data_mw104
_audit_creation_date               2022-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_author_name                 'Farzaneh Fadaei Tirani'
_audit_contact_author              'Farzaneh Fadaei Tirani'
_audit_contact_author_address
;
   Dr. Farzaneh Fadaei Tirani
   EPFL SB ISIC-GE 
   BCH 2111 (Batochime UNIL)
   Av. F.-A. Forel 2 
   CH-1015 Lausanne
   Suisse
;
_audit_contact_author_email        farzaneh.fadaeitirani@epfl.ch
_audit_contact_author_phone        '+41 21 693 9840'
_publ_contact_author_id_orcid      https://orcid.org/0000-0002-7515-7593
_publ_section_references
;
CrysAlisPro Software System, Rigaku Oxford Diffraction, (2022).
Sheldrick, G.M., ShelXT-Integrated space-group and
 crystal-structure determination, Acta Cryst., (2015), A71, 3-8.
Sheldrick, G.M., Crystal structure refinement with ShelXL,
 Acta Cryst., (2015), C71, 3-8.
O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann,
 Olex2: A complete structure solution, refinement and analysis program,
 J. Appl. Cryst., (2009), 42, 339-341.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C23 H29 N3 O3'
_chemical_formula_sum              'C23 H29 N3 O3'
_chemical_formula_weight           395.49
_chemical_absolute_configuration   rmad
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C23 H29 N3 O3'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     8.62694(9)
_cell_length_b                     9.63515(10)
_cell_length_c                     13.05694(13)
_cell_angle_alpha                  90
_cell_angle_beta                   104.0421(11)
_cell_angle_gamma                  90
_cell_volume                       1052.89(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      14836
_cell_measurement_temperature      140.00(10)
_cell_measurement_theta_max        75.8350
_cell_measurement_theta_min        3.4460
_shelx_estimated_absorpt_T_max     0.980
_shelx_estimated_absorpt_T_min     0.758
_exptl_absorpt_coefficient_mu      0.668
_exptl_absorpt_correction_T_max    1.000
_exptl_absorpt_correction_T_min    0.711
_exptl_absorpt_correction_type     Gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.247
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               424
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0 0 1 0.0095
 0 0 -1 0.0229
 -1 0 0 0.0328
 1 0 0 0.0172
 0 1 0 0.2158
 0 -1 0 0.2292
 2 -2 -1 0.1532

_exptl_crystal_size_max            0.44
_exptl_crystal_size_mid            0.06
_exptl_crystal_size_min            0.03
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0.0000 0.0000 1.0000 -0.1205 0.0124 -0.0105
 -0.0000 -0.0000 -1.0000 0.1205 -0.0124 0.0105
 -1.0000 0.0000 -0.0000 0.0649 0.1699 -0.0281
 1.0000 -0.0000 0.0000 -0.0649 -0.1699 0.0281
 -0.0000 1.0000 0.0000 -0.0105 0.0299 0.1568
 0.0000 -1.0000 -0.0000 0.0105 -0.0299 -0.1568
 2.0000 -2.0000 -1.0000 0.0115 -0.4120 -0.2468

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0291
_diffrn_reflns_av_unetI/netI       0.0187
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         16
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              22457
_diffrn_reflns_point_group_measured_fraction_full  0.972
_diffrn_reflns_point_group_measured_fraction_max  0.955
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           76.065
_diffrn_reflns_theta_min           3.489
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        140.00(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.2817
_diffrn_detector_type              AtlasS2
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -111.00 -62.00   1.00    2.00    --  -40.91-148.00 -29.00   49
  2  ω    -81.00  -5.00   1.00    2.00    --  -40.91 123.00-145.00   76
  3  ω     49.00  94.00   1.00    2.00    --   40.91-123.00 134.00   45
  4  ω     42.00  68.00   1.00    8.00    --  112.00-123.00 134.00   26
  5  ω    101.00 126.00   1.00    8.00    --  112.00 148.00  18.00   25
  6  ω     71.00 110.00   1.00    8.00    --  112.00-123.00 134.00   39
  7  ω    114.00 139.00   1.00    8.00    --  112.00 123.00-145.00   25
  8  ω      5.00  30.00   1.00    2.00    --   38.00  79.00 152.90   25
  9  ω   -112.00 -49.00   1.00    2.00    --  -40.91 -57.00  60.00   63
 10  ω    -46.00 -13.00   1.00    2.00    --  -40.91 -57.00  60.00   33
 11  ω    -78.00 -16.00   1.00    2.00    --  -40.91 -38.00 120.00   62
 12  ω     30.00  65.00   1.00    2.00    --   40.91-125.00-150.00   35
 13  ω      9.00  34.00   1.00    2.00    --   40.91  73.00-131.61   25
 14  ω    -14.00  69.00   1.00    2.00    --   40.91 -57.00   0.00   83
 15  ω     14.00  39.00   1.00    2.00    --   46.00  76.00 -10.50   25
 16  ω     12.00  37.00   1.00    2.00    --   46.00  82.00-172.45   25
 17  ω     16.00  41.00   1.00    2.00    --   50.00  82.00   3.64   25
 18  ω     16.00  42.00   1.00    2.00    --   50.00  82.00-130.44   26
 19  ω     16.00  42.00   1.00    2.00    --   50.00  82.00  34.96   26
 20  ω     16.00  41.00   1.00    2.00    --   50.00  81.00 -44.44   25
 21  ω     85.00 119.00   1.00    2.00    --   54.00  71.00 -57.52   34
 22  ω     23.00  67.00   1.00    2.00    --   54.00  71.00 -57.52   44
 23  ω     28.00  54.00   1.00    2.00    --   58.00  71.00 100.22   26
 24  ω     33.00  65.00   1.00    2.00    --   62.00  63.00-104.63   32
 25  ω     35.00  67.00   1.00    2.00    --   66.00  71.00 -33.46   32
 26  ω     36.00  69.00   1.00    2.00    --   66.00  71.00 161.09   33
 27  ω    107.00 134.00   1.00    2.00    --   66.00  68.00 126.15   27
 28  ω     37.00  64.00   1.00    2.00    --   66.00  68.00 126.15   27
 29  ω     68.00 128.00   1.00    2.00    --   66.00  71.00 -33.46   60
 30  ω     37.00  62.00   1.00    2.00    --   66.00  65.00  46.76   25
 31  ω     39.00  69.00   1.00    2.00    --   70.00  71.00  61.28   30
 32  ω    106.00 132.00   1.00    2.00    --   70.00  71.00  61.28   26
 33  ω    101.00 147.00   1.00    2.00    --   74.00  71.00 128.19   46
 34  ω     44.00 139.00   1.00    2.00    --   74.00  68.00  -7.02   95
 35  ω     95.00 121.00   1.00    2.00    --   74.00  63.00-160.78   26
 36  ω     43.00  69.00   1.00    2.00    --   74.00  71.00 128.19   26
 37  ω     45.00  83.00   1.00    2.00    --   74.00  63.00-160.78   38
 38  ω     48.00 101.00   1.00    8.00    --   78.00  65.00-109.21   53
 39  ω     49.00  84.00   1.00    8.00    --   78.00  59.00 -61.24   35
 40  ω     50.00  97.00   1.00    8.00    --   78.00  67.00 138.60   47
 41  ω     53.00  79.00   1.00    8.00    --   82.00  71.00  43.33   26
 42  ω     69.00  96.00   1.00    8.00    --   98.00  61.00  54.44   27
 43  ω    125.00 151.00   1.00    8.00    --  110.00  54.00 -98.40   26
 44  ω     82.00 111.00   1.00    8.00    --  110.00  54.00 -98.40   29
 45  ω     83.00 109.00   1.00    8.00    --  112.00  61.00   0.00   26
 46  ω     29.00 106.00   1.00    8.00    --  112.00 -94.00-180.00   77
 47  ω     36.00  76.00   1.00    8.00    --  112.00 -77.00 -60.00   40
 48  ω     84.00 123.00   1.00    8.00    --  112.00  61.00-150.00   39
 49  ω    143.00 169.00   1.00    8.00    --  112.00  61.00  90.00   26
 50  ω     84.00 140.00   1.00    8.00    --  112.00  61.00  90.00   56
 51  ω    130.00 177.00   1.00    8.00    --  112.00  61.00  60.00   47
 52  ω     35.00  92.00   1.00    8.00    --  112.00 -94.00  90.00   57
 53  ω     83.00 174.00   1.00    8.00    --  112.00  61.00 120.00   91
 54  ω    104.00 170.00   1.00    8.00    --  112.00 111.00 -30.00   66
 55  ω     83.00 121.00   1.00    8.00    --  112.00  61.00  60.00   38
 56  ω     84.00 173.00   1.00    8.00    --  112.00  61.00  30.00   89
 57  ω     81.00 117.00   1.00    8.00    --  112.00  69.00  -0.27   36
 58  ω    149.00 175.00   1.00    8.00    --  112.00  45.00-150.00   26
 59  ω    118.00 167.00   1.00    8.00    --  112.00  61.00 150.00   49
 60  ω     90.00 116.00   1.00    8.00    --  112.00  45.00-150.00   26
 61  ω     85.00 159.00   1.00    8.00    --  112.00  57.00 -88.77   74
 62  ω    131.00 176.00   1.00    8.00    --  112.00  61.00-180.00   45
 63  ω     84.00 166.00   1.00    8.00    --  112.00  61.00 -30.00   82
 64  ω     83.00 109.00   1.00    8.00    --  112.00  61.00 150.00   26
 65  ω     83.00 123.00   1.00    8.00    --  112.00  61.00-120.00   40
 66  ω     85.00 111.00   1.00    8.00    --  112.00  61.00-180.00   26
 67  ω     45.00  81.00   1.00    8.00    --  112.00 -61.00-120.00   36
 68  ω    101.00 139.00   1.00    8.00    --  112.00 -61.00-120.00   38
 69  ω     79.00 109.00   1.00    8.00    --  112.00-111.00 -60.00   30
 70  ω     82.00 164.00   1.00    8.00    --  112.00  65.00-141.43   82
 71  ω     39.00  79.00   1.00    8.00    --  112.00-111.00 -90.00   40
 72  ω     47.00  79.00   1.00    8.00    --  112.00 -94.00 150.00   32
 73  ω     83.00 111.00   1.00    8.00    --  112.00  61.00 -60.00   28
 74  ω     40.00 107.00   1.00    8.00    --  112.00-111.00 150.00   67
 75  ω     84.00 166.00   1.00    8.00    --  112.00  60.00 -70.13   82
 76  ω    135.00 161.00   1.00    8.00    --  112.00  45.00 -30.00   26
 77  ω     80.00 106.00   1.00    8.00    --  112.00-111.00  60.00   26
 78  ω     86.00 113.00   1.00    8.00    --  112.00  45.00 -30.00   27
 79  ω    129.00 154.00   1.00    8.00    --  112.00  45.00-180.00   25
 80  ω     82.00 108.00   1.00    8.00    --  112.00-111.00 -90.00   26
 81  ω     36.00  66.00   1.00    8.00    --  112.00-111.00  60.00   30
 82  ω     89.00 116.00   1.00    8.00    --  112.00  45.00-180.00   27
 83  ω    153.00 178.00   1.00    8.00    --  112.00  61.00   0.00   25
 84  ω     44.00  70.00   1.00    8.00    --  112.00-111.00   0.00   26
 85  ω     82.00 109.00   1.00    8.00    --  112.00-111.00   0.00   27
 86  ω    102.00 141.00   1.00    8.00    --  112.00 -77.00 -60.00   39
 87  ω     60.00  85.00   1.00    8.00    --  112.00-148.00 -29.00   25
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0649411000
_diffrn_orient_matrix_UB_12        -0.0104568000
_diffrn_orient_matrix_UB_13        -0.1204986000
_diffrn_orient_matrix_UB_21        -0.1699292000
_diffrn_orient_matrix_UB_22        0.0298933000
_diffrn_orient_matrix_UB_23        0.0123526000
_diffrn_orient_matrix_UB_31        0.0281463000
_diffrn_orient_matrix_UB_32        0.1567705000
_diffrn_orient_matrix_UB_33        -0.0104981000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.807
_reflns_Friedel_fraction_full      0.940
_reflns_Friedel_fraction_max       0.908
_reflns_number_gt                  4093
_reflns_number_total               4195
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection         'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction          'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max           0.242
_refine_diff_density_min           -0.165
_refine_diff_density_rms           0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.01(6)
_refine_ls_extinction_coef         0.0045(5)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       307
_refine_ls_number_reflns           4195
_refine_ls_number_restraints       74
_refine_ls_R_factor_all            0.0313
_refine_ls_R_factor_gt             0.0303
_refine_ls_restrained_S_all        1.063
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0309P)²+0.2652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0752
_refine_ls_wR_factor_ref           0.0761
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C10B-C11 = C9B-C10B
 1.54 with sigma of 0.005
 C9A-C10A \\sim C10B-C9B
 with sigma of 0.02
 N3A-C8 \\sim N3B-C8
 with sigma of 0.02
 N3A-C10A \\sim N3B-C10B
 with sigma of 0.02
 N3A-C9A \\sim N3B-C9B
 with sigma of 0.02
 N3A-H3A \\sim N3B-H3B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N3A \\sim N3B \\sim C9A \\sim C9B \\sim C10A \\sim C10B: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N3B)=Sof(H3B)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C10B)=Sof(H10C)=Sof(H10D)=
 Sof(H11A)=1-FVAR(1)
 Sof(N3A)=Sof(H3A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=
 Sof(H11)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C11(H11A)
5.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB), C10A(H10A,H10B), C10B(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     difmap
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 1.27549(18) 0.23715(16) 0.31592(11) 0.0300(3) Uani 1 1 d . . . . .
 O2 O 1.02849(17) 0.58329(15) 0.49193(12) 0.0310(3) Uani 1 1 d . . . . .
 O3 O 0.73001(18) 0.24014(15) 0.64084(11) 0.0301(3) Uani 1 1 d . . . . .
 N1 N 1.21525(18) 0.43802(18) 0.38675(12) 0.0215(3) Uani 1 1 d . . . . .
 H1 H 1.217(3) 0.523(3) 0.3858(19) 0.026 Uiso 1 1 d . U . . .
 N2 N 0.91564(18) 0.38274(18) 0.52690(12) 0.0213(3) Uani 1 1 d . . . . .
 H2 H 0.919(3) 0.297(3) 0.5249(17) 0.024(6) Uiso 1 1 d . . . . .
 N3A N 0.7470(3) 0.4417(2) 0.73531(16) 0.0237(5) Uani 0.862(4) 1 d D U P A 1
 H3A H 0.752(4) 0.530(3) 0.733(2) 0.028 Uiso 0.862(4) 1 d D U P A 1
 N3B N 0.6575(19) 0.4338(13) 0.7027(10) 0.023(2) Uani 0.138(4) 1 d D U P A 2
 H3B H 0.65(2) 0.523(5) 0.704(14) 0.027 Uiso 0.138(4) 1 d D U P A 2
 C1 C 1.3200(3) 0.4488(2) 0.23146(15) 0.0309(4) Uani 1 1 d . . . . .
 H1A H 1.418369 0.409512 0.218618 0.046 Uiso 1 1 calc R U . . .
 H1B H 1.339196 0.545200 0.255133 0.046 Uiso 1 1 calc R U . . .
 H1C H 1.235398 0.446087 0.166059 0.046 Uiso 1 1 calc R U . . .
 C2 C 1.2695(2) 0.3654(2) 0.31525(14) 0.0224(4) Uani 1 1 d . . . . .
 C3 C 1.1627(2) 0.3699(2) 0.47193(14) 0.0221(4) Uani 1 1 d . . . . .
 H3 H 1.120787 0.275646 0.447727 0.027 Uiso 1 1 calc R U . . .
 C4 C 1.2976(2) 0.3546(3) 0.57118(16) 0.0326(5) Uani 1 1 d . . . . .
 H4A H 1.383064 0.297675 0.555375 0.049 Uiso 1 1 calc R U . . .
 H4B H 1.256715 0.309795 0.626681 0.049 Uiso 1 1 calc R U . . .
 H4C H 1.339884 0.446517 0.595277 0.049 Uiso 1 1 calc R U . . .
 C5 C 1.0280(2) 0.4557(2) 0.49645(14) 0.0209(4) Uani 1 1 d . . . . .
 C6 C 0.7822(2) 0.4505(2) 0.55700(14) 0.0223(4) Uani 1 1 d . . . . .
 H6 H 0.814724 0.546614 0.582154 0.027 Uiso 1 1 calc R U . . .
 C7 C 0.6376(2) 0.4586(3) 0.46355(17) 0.0367(5) Uani 1 1 d . . . . .
 H7A H 0.667115 0.506842 0.404943 0.055 Uiso 1 1 calc R U . . .
 H7B H 0.551707 0.509706 0.484144 0.055 Uiso 1 1 calc R U . . .
 H7C H 0.600856 0.364647 0.441313 0.055 Uiso 1 1 calc R U . . .
 C8 C 0.7472(2) 0.3671(2) 0.64783(15) 0.0249(4) Uani 1 1 d D . . . .
 C9A C 0.7275(3) 0.3784(3) 0.83300(16) 0.0254(5) Uani 0.862(4) 1 d D U P A 1
 H9AA H 0.815929 0.409202 0.892116 0.031 Uiso 0.862(4) 1 calc R U P A 1
 H9AB H 0.734931 0.276274 0.827235 0.031 Uiso 0.862(4) 1 calc R U P A 1
 C9B C 0.5783(16) 0.3676(15) 0.7776(9) 0.023(2) Uani 0.138(4) 1 d D U P A 2
 H9BA H 0.594834 0.265951 0.776655 0.027 Uiso 0.138(4) 1 calc R U P A 2
 H9BB H 0.461934 0.385446 0.755107 0.027 Uiso 0.138(4) 1 calc R U P A 2
 C10A C 0.5684(3) 0.4153(2) 0.85799(18) 0.0226(5) Uani 0.862(4) 1 d D U P A 1
 H10A H 0.548679 0.350748 0.912433 0.027 Uiso 0.862(4) 1 calc R U P A 1
 H10B H 0.481257 0.402925 0.793595 0.027 Uiso 0.862(4) 1 calc R U P A 1
 C10B C 0.6424(18) 0.4218(10) 0.8906(9) 0.027(3) Uani 0.138(4) 1 d D U P A 2
 H10C H 0.760172 0.430403 0.906695 0.032 Uiso 0.138(4) 1 calc R U P A 2
 H10D H 0.614270 0.356687 0.941917 0.032 Uiso 0.138(4) 1 calc R U P A 2
 C11 C 0.5650(3) 0.5663(2) 0.89803(15) 0.0300(4) Uani 1 1 d D . . . .
 H11 H 0.601371 0.627179 0.846386 0.036 Uiso 0.862(4) 1 calc R U P A 1
 H11A H 0.601116 0.628135 0.846838 0.036 Uiso 0.138(4) 1 calc R U P A 2
 C12 C 0.6761(2) 0.5953(2) 1.00658(16) 0.0277(4) Uani 1 1 d . . . . .
 C13 C 0.7389(3) 0.7278(2) 1.02934(17) 0.0332(5) Uani 1 1 d . . . . .
 H13 H 0.713589 0.797597 0.976516 0.040 Uiso 1 1 calc R U . . .
 C14 C 0.8375(3) 0.7610(3) 1.12702(19) 0.0386(5) Uani 1 1 d . . . . .
 H14 H 0.878104 0.852573 1.140495 0.046 Uiso 1 1 calc R U . . .
 C15 C 0.8763(3) 0.6609(3) 1.20454(19) 0.0375(5) Uani 1 1 d . . . . .
 H15 H 0.944606 0.682486 1.271379 0.045 Uiso 1 1 calc R U . . .
 C16 C 0.8148(3) 0.5291(3) 1.1837(2) 0.0456(6) Uani 1 1 d . . . . .
 H16 H 0.840571 0.459753 1.236848 0.055 Uiso 1 1 calc R U . . .
 C17 C 0.7156(3) 0.4962(2) 1.08590(18) 0.0400(5) Uani 1 1 d . . . . .
 H17 H 0.674286 0.404748 1.073165 0.048 Uiso 1 1 calc R U . . .
 C18 C 0.3916(3) 0.6032(2) 0.89123(15) 0.0294(4) Uani 1 1 d . . . . .
 C19 C 0.3242(3) 0.5980(2) 0.97743(15) 0.0283(4) Uani 1 1 d . . . . .
 H19 H 0.389477 0.575716 1.045113 0.034 Uiso 1 1 calc R U . . .
 C20 C 0.1625(3) 0.6250(2) 0.96623(18) 0.0337(5) Uani 1 1 d . . . . .
 H20 H 0.118779 0.620670 1.026275 0.040 Uiso 1 1 calc R U . . .
 C21 C 0.0644(3) 0.6582(3) 0.86839(19) 0.0393(5) Uani 1 1 d . . . . .
 H21 H -0.045860 0.677021 0.861058 0.047 Uiso 1 1 calc R U . . .
 C22 C 0.1295(3) 0.6632(3) 0.78242(19) 0.0417(6) Uani 1 1 d . . . . .
 H22 H 0.063346 0.684823 0.714886 0.050 Uiso 1 1 calc R U . . .
 C23 C 0.2896(3) 0.6373(2) 0.79290(17) 0.0393(6) Uani 1 1 d . . . . .
 H23 H 0.332166 0.642592 0.732385 0.047 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C2 1.237(3) . ?
 O2 C5 1.231(3) . ?
 O3 C8 1.233(3) . ?
 N1 H1 0.82(3) . ?
 N1 C2 1.339(2) . ?
 N1 C3 1.455(2) . ?
 N2 H2 0.82(3) . ?
 N2 C5 1.334(2) . ?
 N2 C6 1.458(2) . ?
 N3A H3A 0.86(3) . ?
 N3A C8 1.350(3) . ?
 N3A C9A 1.460(3) . ?
 N3B H3B 0.86(4) . ?
 N3B C8 1.338(12) . ?
 N3B C9B 1.469(14) . ?
 C1 H1A 0.9800 . ?
 C1 H1B 0.9800 . ?
 C1 H1C 0.9800 . ?
 C1 C2 1.505(3) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.525(3) . ?
 C3 C5 1.522(2) . ?
 C4 H4A 0.9800 . ?
 C4 H4B 0.9800 . ?
 C4 H4C 0.9800 . ?
 C6 H6 1.0000 . ?
 C6 C7 1.520(3) . ?
 C6 C8 1.522(3) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 H7C 0.9800 . ?
 C9A H9AA 0.9900 . ?
 C9A H9AB 0.9900 . ?
 C9A C10A 1.528(3) . ?
 C9B H9BA 0.9900 . ?
 C9B H9BB 0.9900 . ?
 C9B C10B 1.536(7) . ?
 C10A H10A 0.9900 . ?
 C10A H10B 0.9900 . ?
 C10A C11 1.548(3) . ?
 C10B H10C 0.9900 . ?
 C10B H10D 0.9900 . ?
 C10B C11 1.558(7) . ?
 C11 H11 1.0000 . ?
 C11 H11A 1.0000 . ?
 C11 C12 1.532(3) . ?
 C11 C18 1.519(3) . ?
 C12 C13 1.390(3) . ?
 C12 C17 1.389(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.388(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.380(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.378(4) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.390(4) . ?
 C17 H17 0.9500 . ?
 C18 C19 1.387(3) . ?
 C18 C23 1.408(3) . ?
 C19 H19 0.9500 . ?
 C19 C20 1.392(3) . ?
 C20 H20 0.9500 . ?
 C20 C21 1.388(3) . ?
 C21 H21 0.9500 . ?
 C21 C22 1.373(4) . ?
 C22 H22 0.9500 . ?
 C22 C23 1.377(4) . ?
 C23 H23 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C2 N1 H1 120.2(17) . . ?
 C2 N1 C3 121.58(17) . . ?
 C3 N1 H1 118.1(17) . . ?
 C5 N2 H2 118.6(17) . . ?
 C5 N2 C6 121.54(17) . . ?
 C6 N2 H2 119.8(17) . . ?
 C8 N3A H3A 119(2) . . ?
 C8 N3A C9A 122.7(2) . . ?
 C9A N3A H3A 118(2) . . ?
 C8 N3B H3B 121(10) . . ?
 C8 N3B C9B 124.8(11) . . ?
 C9B N3B H3B 114(10) . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 O1 C2 N1 122.56(18) . . ?
 O1 C2 C1 121.33(17) . . ?
 N1 C2 C1 116.09(17) . . ?
 N1 C3 H3 108.9 . . ?
 N1 C3 C4 112.20(15) . . ?
 N1 C3 C5 108.13(16) . . ?
 C4 C3 H3 108.9 . . ?
 C5 C3 H3 108.9 . . ?
 C5 C3 C4 109.77(15) . . ?
 C3 C4 H4A 109.5 . . ?
 C3 C4 H4B 109.5 . . ?
 C3 C4 H4C 109.5 . . ?
 H4A C4 H4B 109.5 . . ?
 H4A C4 H4C 109.5 . . ?
 H4B C4 H4C 109.5 . . ?
 O2 C5 N2 123.50(17) . . ?
 O2 C5 C3 121.37(17) . . ?
 N2 C5 C3 115.07(17) . . ?
 N2 C6 H6 109.0 . . ?
 N2 C6 C7 110.76(16) . . ?
 N2 C6 C8 107.02(15) . . ?
 C7 C6 H6 109.0 . . ?
 C7 C6 C8 111.93(16) . . ?
 C8 C6 H6 109.0 . . ?
 C6 C7 H7A 109.5 . . ?
 C6 C7 H7B 109.5 . . ?
 C6 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 O3 C8 N3A 124.48(19) . . ?
 O3 C8 N3B 116.2(6) . . ?
 O3 C8 C6 120.59(17) . . ?
 N3A C8 C6 114.81(18) . . ?
 N3B C8 C6 114.4(5) . . ?
 N3A C9A H9AA 109.0 . . ?
 N3A C9A H9AB 109.0 . . ?
 N3A C9A C10A 112.9(2) . . ?
 H9AA C9A H9AB 107.8 . . ?
 C10A C9A H9AA 109.0 . . ?
 C10A C9A H9AB 109.0 . . ?
 N3B C9B H9BA 109.2 . . ?
 N3B C9B H9BB 109.2 . . ?
 N3B C9B C10B 112.0(10) . . ?
 H9BA C9B H9BB 107.9 . . ?
 C10B C9B H9BA 109.2 . . ?
 C10B C9B H9BB 109.2 . . ?
 C9A C10A H10A 109.1 . . ?
 C9A C10A H10B 109.1 . . ?
 C9A C10A C11 112.5(2) . . ?
 H10A C10A H10B 107.8 . . ?
 C11 C10A H10A 109.1 . . ?
 C11 C10A H10B 109.1 . . ?
 C9B C10B H10C 110.2 . . ?
 C9B C10B H10D 110.2 . . ?
 C9B C10B C11 107.7(9) . . ?
 H10C C10B H10D 108.5 . . ?
 C11 C10B H10C 110.2 . . ?
 C11 C10B H10D 110.2 . . ?
 C10A C11 H11 106.8 . . ?
 C10B C11 H11A 106.5 . . ?
 C12 C11 C10A 115.15(18) . . ?
 C12 C11 C10B 92.3(5) . . ?
 C12 C11 H11 106.8 . . ?
 C12 C11 H11A 106.5 . . ?
 C18 C11 C10A 107.43(18) . . ?
 C18 C11 C10B 129.5(6) . . ?
 C18 C11 H11 106.8 . . ?
 C18 C11 H11A 106.5 . . ?
 C18 C11 C12 113.41(16) . . ?
 C13 C12 C11 119.29(18) . . ?
 C17 C12 C11 123.3(2) . . ?
 C17 C12 C13 117.3(2) . . ?
 C12 C13 H13 119.1 . . ?
 C14 C13 C12 121.9(2) . . ?
 C14 C13 H13 119.1 . . ?
 C13 C14 H14 120.0 . . ?
 C15 C14 C13 119.9(2) . . ?
 C15 C14 H14 120.0 . . ?
 C14 C15 H15 120.5 . . ?
 C16 C15 C14 119.1(2) . . ?
 C16 C15 H15 120.5 . . ?
 C15 C16 H16 119.6 . . ?
 C15 C16 C17 120.9(2) . . ?
 C17 C16 H16 119.6 . . ?
 C12 C17 C16 120.9(2) . . ?
 C12 C17 H17 119.6 . . ?
 C16 C17 H17 119.6 . . ?
 C19 C18 C11 123.00(18) . . ?
 C19 C18 C23 117.1(2) . . ?
 C23 C18 C11 119.79(18) . . ?
 C18 C19 H19 119.5 . . ?
 C18 C19 C20 120.98(19) . . ?
 C20 C19 H19 119.5 . . ?
 C19 C20 H20 119.6 . . ?
 C21 C20 C19 120.8(2) . . ?
 C21 C20 H20 119.6 . . ?
 C20 C21 H21 120.6 . . ?
 C22 C21 C20 118.8(2) . . ?
 C22 C21 H21 120.6 . . ?
 C21 C22 H22 119.6 . . ?
 C21 C22 C23 120.8(2) . . ?
 C23 C22 H22 119.6 . . ?
 C18 C23 H23 119.2 . . ?
 C22 C23 C18 121.5(2) . . ?
 C22 C23 H23 119.2 . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 N1 H1 O3 0.82(3) 2.19(3) 2.985(2) 164(2) 2_756 yes
 N2 H2 O2 0.82(3) 2.13(3) 2.945(2) 168(2) 2_746 yes
 N3A H3A O1 0.86(3) 2.09(3) 2.920(3) 164(3) 2_756 yes
 N3B H3B O1 0.86(4) 2.19(8) 3.001(13) 159(17) 2_756 yes
 C1 H1B O3 0.98 2.47 3.346(3) 148.0 2_756 yes
 C3 H3 O2 1.00 2.49 3.309(2) 138.6 2_746 yes
 C6 H6 O1 1.00 2.50 3.321(2) 139.1 2_756 yes

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N1 C3 C5 O2 -36.3(2) . . . . ?
 N1 C3 C5 N2 146.45(16) . . . . ?
 N2 C6 C8 O3 -50.4(2) . . . . ?
 N2 C6 C8 N3A 125.72(19) . . . . ?
 N2 C6 C8 N3B 163.4(7) . . . . ?
 N3A C9A C10A C11 -74.3(3) . . . . ?
 N3B C9B C10B C11 77.9(14) . . . . ?
 C2 N1 C3 C4 91.5(2) . . . . ?
 C2 N1 C3 C5 -147.33(17) . . . . ?
 C3 N1 C2 O1 1.4(3) . . . . ?
 C3 N1 C2 C1 -179.98(17) . . . . ?
 C4 C3 C5 O2 86.5(2) . . . . ?
 C4 C3 C5 N2 -90.8(2) . . . . ?
 C5 N2 C6 C7 94.5(2) . . . . ?
 C5 N2 C6 C8 -143.28(17) . . . . ?
 C6 N2 C5 O2 0.4(3) . . . . ?
 C6 N2 C5 C3 177.63(16) . . . . ?
 C7 C6 C8 O3 71.1(2) . . . . ?
 C7 C6 C8 N3A -112.8(2) . . . . ?
 C7 C6 C8 N3B -75.1(8) . . . . ?
 C8 N3A C9A C10A -111.2(3) . . . . ?
 C8 N3B C9B C10B 116.7(14) . . . . ?
 C9A N3A C8 O3 0.6(4) . . . . ?
 C9A N3A C8 C6 -175.4(2) . . . . ?
 C9A C10A C11 C12 -67.9(2) . . . . ?
 C9A C10A C11 C18 164.72(18) . . . . ?
 C9B N3B C8 O3 18.1(17) . . . . ?
 C9B N3B C8 C6 165.9(11) . . . . ?
 C9B C10B C11 C12 -170.0(9) . . . . ?
 C9B C10B C11 C18 66.7(11) . . . . ?
 C10A C11 C12 C13 150.68(19) . . . . ?
 C10A C11 C12 C17 -30.9(3) . . . . ?
 C10A C11 C18 C19 98.8(2) . . . . ?
 C10A C11 C18 C23 -77.5(2) . . . . ?
 C10B C11 C12 C13 139.6(6) . . . . ?
 C10B C11 C12 C17 -41.9(6) . . . . ?
 C10B C11 C18 C19 84.9(6) . . . . ?
 C10B C11 C18 C23 -91.5(6) . . . . ?
 C11 C12 C13 C14 178.6(2) . . . . ?
 C11 C12 C17 C16 -178.8(2) . . . . ?
 C11 C18 C19 C20 -176.23(19) . . . . ?
 C11 C18 C23 C22 176.0(2) . . . . ?
 C12 C11 C18 C19 -29.6(3) . . . . ?
 C12 C11 C18 C23 154.03(19) . . . . ?
 C12 C13 C14 C15 0.4(4) . . . . ?
 C13 C12 C17 C16 -0.3(4) . . . . ?
 C13 C14 C15 C16 -0.6(4) . . . . ?
 C14 C15 C16 C17 0.4(4) . . . . ?
 C15 C16 C17 C12 0.1(4) . . . . ?
 C17 C12 C13 C14 0.1(3) . . . . ?
 C18 C11 C12 C13 -85.0(2) . . . . ?
 C18 C11 C12 C17 93.5(3) . . . . ?
 C18 C19 C20 C21 -0.1(3) . . . . ?
 C19 C18 C23 C22 -0.6(3) . . . . ?
 C19 C20 C21 C22 0.3(4) . . . . ?
 C20 C21 C22 C23 -0.7(4) . . . . ?
 C21 C22 C23 C18 0.8(4) . . . . ?
 C23 C18 C19 C20 0.2(3) . . . . ?

_olex2_date_sample_data_collection  2022-04-19
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max  1.498
_oxdiff_exptl_absorpt_empirical_full_min  0.641
