# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BNIMOKETUV
_database_code_depnum_ccdc_archive 'CCDC 2233460'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_BNIMOKETUV          
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.06 Note  
RESPONSE: This value is not correct, since it is stated for a centrosymmetric
 space group. The actual Data / Parameter Ratio for the P2(1) group is 11.1,
 which is maximal for Cu Kalpha radiation and d(min)=0.772A.
;
_audit_creation_date             2021-12-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H20 N2 O4'
_chemical_oxdiff_usercomment     BNIMOKETUV
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                   11.38512(6)
_cell_length_b                   9.48447(4)
_cell_length_c                   15.80604(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.6652(6)
_cell_angle_gamma                90
_cell_volume                     1596.950(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39851
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.3290
_cell_measurement_theta_min      2.9590
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.767
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.83418
_exptl_absorpt_correction_T_min  0.83014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41676
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.491
_diffrn_reflns_theta_min         2.988
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00 121.00   0.40    0.05    --   48.63  77.00  90.00  235
  2  ω     27.00 121.00   0.40    0.05    --   48.63  77.00 150.00  235
  3  ω     39.00 121.00   0.40    0.05    --   48.63  38.00  90.00  205
  4  ω     39.00 123.00   0.40    0.05    --   48.63  25.00  30.00  210
  5  ω     27.00 121.00   0.40    0.05    --   48.63  77.00-180.00  235
  6  ω    -31.00  25.00   0.40    0.05    --  -48.63  25.00  30.00  140
  7  ω   -121.00 -39.00   0.40    0.05    --  -48.63 -38.00 150.00  205
  8  ω   -123.00 -37.00   0.40    0.05    --  -48.63 -25.00-133.00  215
  9  ω    100.00 126.00   0.40    0.20    --  111.50 -82.00 166.48   65
 10  ω     81.00 107.00   0.40    0.20    --  111.50-147.00  25.41   65
 11  ω     51.00 101.00   0.40    0.20    --  111.50-125.00 -60.00  125
 12  ω     63.00 104.20   0.40    0.20    --  111.50-125.00-120.00  103
 13  ω     92.00 118.00   0.40    0.20    --  111.50-133.00-166.62   65
 14  ω     42.00  81.20   0.40    0.20    --  111.50-133.00-166.62   98
 15  ω     45.00  71.00   0.40    0.20    --  111.50-125.00-180.00   65
 16  ω     40.00  77.20   0.40    0.20    --  111.50-111.00 -75.51   93
 17  ω     34.00  94.00   0.40    0.05    --   48.63-125.00-120.00  150
 18  ω     41.00  72.20   0.40    0.20    --  111.50-107.00-157.95   78
 19  ω     82.00 108.00   0.40    0.20    --  111.50-111.00 -75.51   65
 20  ω     56.00  82.00   0.40    0.20    --  111.50-103.00 -57.47   65
 21  ω     42.00  91.20   0.40    0.20    --  111.50-122.00  38.98  123
 22  ω     66.00  96.00   0.40    0.20    --  111.50 -95.00   0.00   75
 23  ω     42.00 102.00   0.40    0.20    --  111.50 -99.00 109.09  150
 24  ω     64.00  90.00   0.40    0.20    --  111.50 -95.00 120.00   65
 25  ω     80.00 106.00   0.40    0.20    --  111.50-119.00 175.83   65
 26  ω     43.00  93.00   0.40    0.20    --  111.50 -95.00 150.00  125
 27  ω     41.00  70.20   0.40    0.20    --  111.50-125.00  90.00   73
 28  ω     70.00  96.00   0.40    0.20    --  111.50 -95.00  30.00   65
 29  ω     40.00  65.20   0.40    0.20    --  111.50 -95.00  30.00   63
 30  ω     42.00  71.20   0.40    0.20    --  111.50 -77.00  60.00   73
 31  ω     57.00  88.20   0.40    0.20    --  111.50 -77.00 150.00   78
 32  ω     47.00 104.20   0.40    0.20    --  111.50 -77.00  30.00  143
 33  ω     56.00 104.00   0.40    0.20    --  111.50 -77.00 -30.00  120
 34  ω     46.00  85.20   0.40    0.20    --  111.50 -77.00 -90.00   98
 35  ω     42.00  69.20   0.40    0.20    --  111.50 -61.00 -60.00   68
 36  ω     53.00 103.00   0.40    0.20    --  111.50 -77.00 -60.00  125
 37  ω     46.00  71.20   0.40    0.20    --  111.50 -63.00  -0.18   63
 38  ω     42.00  76.00   0.40    0.20    --  111.50 -67.00  59.07   85
 39  ω    -22.00  25.20   0.40    0.05    --   48.63 -19.00  60.00  118
 40  ω    -25.00  31.00   0.40    0.05    --   48.63 -25.00-133.00  140
 41  ω    123.00 154.20   0.40    0.20    --  111.50  15.00 -60.00   78
 42  ω    146.00 175.20   0.40    0.20    --  111.50  77.00  60.00   73
 43  ω    141.00 168.20   0.40    0.20    --  111.50  77.00  90.00   68
 44  ω     90.00 118.00   0.40    0.20    --  111.50  77.00 150.00   70
 45  ω     90.00 138.00   0.40    0.20    --  111.50  77.00  90.00  120
 46  ω     94.00 121.20   0.40    0.20    --  111.50  77.00 120.00   68
 47  ω     90.00 139.20   0.40    0.20    --  111.50  77.00  60.00  123
 48  ω     93.00 157.00   0.40    0.20    --  111.50  71.00 -44.50  160
 49  ω     90.00 128.00   0.40    0.20    --  111.50  77.00-150.00   95
 50  ω    142.00 171.20   0.40    0.20    --  111.50  77.00-180.00   73
 51  ω    142.00 169.20   0.40    0.20    --  111.50  77.00-150.00   68
 52  ω     90.00 123.20   0.40    0.20    --  111.50  77.00-180.00   83
 53  ω    103.00 129.00   0.40    0.20    --  111.50  62.00  52.98   65
 54  ω     98.00 127.20   0.40    0.20    --  111.50  61.00  90.00   73
 55  ω    138.00 177.20   0.40    0.20    --  111.50  62.00  52.98   98
 56  ω    138.00 163.20   0.40    0.20    --  111.50  61.00  90.00   63
 57  ω     96.00 134.00   0.40    0.20    --  111.50  61.00 120.00   95
 58  ω     96.00 122.00   0.40    0.20    --  111.50  61.00 150.00   65
 59  ω     95.00 177.00   0.40    0.20    --  111.50  65.00 154.82  205
 60  ω    140.00 174.00   0.40    0.20    --  111.50  61.00 120.00   85
 61  ω    102.00 129.20   0.40    0.20    --  111.50  30.00 -30.00   68
 62  ω    120.00 146.00   0.40    0.20    --  111.50  45.00 -90.00   65
 63  ω     98.00 163.20   0.40    0.20    --  111.50  61.00-180.00  163
 64  ω    146.00 175.20   0.40    0.20    --  111.50  45.00-150.00   73
 65  ω    141.00 174.20   0.40    0.20    --  111.50  30.00-120.00   83
 66  ω    106.00 137.20   0.40    0.20    --  111.50  30.00-120.00   78
 67  ω    101.00 177.00   0.40    0.20    --  111.50  25.00  30.00  190
 68  ω    146.00 176.00   0.40    0.20    --  111.50  30.00  90.00   75
 69  ω    152.00 177.20   0.40    0.20    --  111.50  30.00 120.00   63
 70  ω    101.00 135.00   0.40    0.20    --  111.50  30.00 120.00   85
 71  ω    120.00 152.00   0.40    0.20    --  111.50  15.00  90.00   80
 72  ω    102.00 171.20   0.40    0.20    --  111.50  15.00-150.00  173
 73  ω    101.00 154.20   0.40    0.20    --  111.50  15.00-180.00  133
 74  ω    -94.00 -68.80   0.40    0.20    --  -90.00 -77.00-180.00   63
 75  ω    -96.00 -70.00   0.40    0.20    --  -90.00 -77.00-150.00   65
 76  ω    -97.00 -71.00   0.40    0.20    --  -90.00 -77.00  90.00   65
 77  ω    -94.00 -68.80   0.40    0.20    --  -90.00 -77.00 120.00   63
 78  ω    -96.00 -70.00   0.40    0.20    --  -90.00 -77.00 150.00   65
 79  ω    -96.00 -70.80   0.40    0.20    --  -90.00 -72.00 154.63   63
 80  ω    -99.00 -73.00   0.40    0.20    --  -90.00 -73.00 131.59   65
 81  ω   -157.00-129.80   0.40    0.20    --  -90.00 -72.00 154.63   68
 82  ω    -97.00 -71.00   0.40    0.20    --  -90.00 -75.00  72.28   65
 83  ω    -96.20 -71.00   0.40    0.20    --  -90.00 -71.00  89.23   63
 84  ω   -100.00 -74.00   0.40    0.20    --  -90.00 -68.00 160.52   65
 85  ω   -100.00 -72.80   0.40    0.20    --  -90.00 -67.00 153.26   68
 86  ω    -97.00 -71.00   0.40    0.20    --  -90.00 -72.00  72.86   65
 87  ω    -99.00 -73.00   0.40    0.20    --  -90.00 -65.00 164.06   65
 88  ω    -99.00 -73.00   0.40    0.20    --  -90.00 -65.00  93.36   65
 89  ω   -101.00 -75.00   0.40    0.20    --  -90.00 -61.00 120.00   65
 90  ω   -100.20 -75.00   0.40    0.20    --  -90.00 -61.00  86.64   63
 91  ω   -106.00 -76.80   0.40    0.20    --  -90.00 -57.00 163.34   73
 92  ω   -102.20 -77.00   0.40    0.20    --  -90.00 -52.00  97.83   63
 93  ω   -163.00 -79.00   0.40    0.20    --  -90.00 -25.00-133.00  210
 94  ω    -99.00 -73.00   0.40    0.20    --  -90.00 -67.00-172.37   65
 95  ω    -94.20 -69.00   0.40    0.20    --  -90.00 -74.00-167.18   63
 96  ω   -150.00-124.80   0.40    0.20    --  -90.00 -74.00-167.18   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0791495000
_diffrn_orient_matrix_UB_12      -0.0333199000
_diffrn_orient_matrix_UB_13      -0.0589672000
_diffrn_orient_matrix_UB_21      -0.1111123000
_diffrn_orient_matrix_UB_22      0.0424261000
_diffrn_orient_matrix_UB_23      -0.0851980000
_diffrn_orient_matrix_UB_31      0.0479874000
_diffrn_orient_matrix_UB_32      0.1532076000
_diffrn_orient_matrix_UB_33      0.0107492000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                6769
_reflns_number_total             6778
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 3048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.0048(4)
_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   1.040
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         6778
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.040
_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)+(0.0451P)²+0.3879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_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
O1A O 0.67971(11) 0.50027(14) 0.41461(8) 0.0142(2) Uani 1 1 d . . . . .
H1A H 0.654(3) 0.427(3) 0.4328(19) 0.029(7) Uiso 1 1 d . . . . .
O2A O 0.44089(11) 0.50746(13) 0.40254(8) 0.0137(2) Uani 1 1 d . . . . .
H2A H 0.450(3) 0.467(4) 0.353(2) 0.037(8) Uiso 1 1 d . . . . .
O3A O 0.38414(12) 0.75513(15) 0.50553(9) 0.0183(3) Uani 1 1 d . . . . .
O4A O 0.92420(12) 0.95139(16) 0.47924(10) 0.0235(3) Uani 1 1 d . . . . .
N1A N 0.43469(14) 0.86916(17) 0.22474(10) 0.0157(3) Uani 1 1 d . . . . .
N2A N 0.44498(13) 0.73195(15) 0.34234(10) 0.0130(3) Uani 1 1 d . . . . .
C1A C 0.64730(15) 0.62389(19) 0.45153(11) 0.0125(3) Uani 1 1 d . . . . .
C2A C 0.49975(15) 0.63919(18) 0.41961(11) 0.0125(3) Uani 1 1 d . . . . .
C3A C 0.47826(16) 0.6937(2) 0.50574(11) 0.0141(3) Uani 1 1 d . . . . .
C4A C 0.58840(17) 0.6521(2) 0.58185(12) 0.0166(3) Uani 1 1 d . . . . .
H4A H 0.590(2) 0.654(3) 0.6453(19) 0.027(6) Uiso 1 1 d . . . . .
C5A C 0.68109(16) 0.61117(19) 0.55423(11) 0.0147(3) Uani 1 1 d . . . . .
C6A C 0.80520(18) 0.5566(2) 0.61515(13) 0.0197(4) Uani 1 1 d . . . . .
H6A H 0.800(3) 0.521(3) 0.6755(19) 0.033(7) Uiso 1 1 d . . . . .
H6B H 0.865(3) 0.623(4) 0.627(2) 0.051(9) Uiso 1 1 d . . . . .
H6C H 0.832(3) 0.474(4) 0.588(2) 0.043(8) Uiso 1 1 d . . . . .
C7A C 0.71470(15) 0.74883(18) 0.42213(11) 0.0125(3) Uani 1 1 d . . . . .
C8A C 0.71516(16) 0.88454(19) 0.47644(12) 0.0154(3) Uani 1 1 d . . . . .
H8A H 0.629(2) 0.921(3) 0.4613(17) 0.021(6) Uiso 1 1 d . . . . .
H8B H 0.750(2) 0.863(3) 0.5409(16) 0.018(5) Uiso 1 1 d . . . . .
C9A C 0.79811(17) 0.9984(2) 0.45878(13) 0.0201(4) Uani 1 1 d . . . . .
H9A H 0.764(2) 1.028(3) 0.3968(17) 0.017(6) Uiso 1 1 d . . . . .
H9B H 0.798(3) 1.082(3) 0.4960(19) 0.032(7) Uiso 1 1 d . . . . .
C10A C 0.92725(17) 0.8349(2) 0.42269(14) 0.0208(4) Uani 1 1 d . . . . .
H10A H 1.017(2) 0.811(3) 0.4391(17) 0.024(6) Uiso 1 1 d . . . . .
H10B H 0.899(2) 0.864(3) 0.3597(17) 0.021(6) Uiso 1 1 d . . . . .
C11A C 0.85257(16) 0.7094(2) 0.43724(13) 0.0173(3) Uani 1 1 d . . . . .
H11A H 0.900(2) 0.674(3) 0.5000(18) 0.027(7) Uiso 1 1 d . . . . .
H11B H 0.856(2) 0.636(3) 0.3972(16) 0.015(5) Uiso 1 1 d . . . . .
C12A C 0.64601(16) 0.77511(19) 0.32029(11) 0.0147(3) Uani 1 1 d . . . . .
H12A H 0.682(2) 0.851(3) 0.2976(16) 0.015 Uiso 1 1 d . U . . .
H12B H 0.653(2) 0.689(3) 0.2879(17) 0.019(6) Uiso 1 1 d . . . . .
C13A C 0.50852(15) 0.79850(18) 0.29513(11) 0.0129(3) Uani 1 1 d . . . . .
C14A C 0.31320(16) 0.8439(2) 0.22400(12) 0.0156(3) Uani 1 1 d . . . . .
C15A C 0.19750(17) 0.8888(2) 0.16187(12) 0.0201(4) Uani 1 1 d . . . . .
H15A H 0.192(2) 0.949(3) 0.1120(19) 0.030(7) Uiso 1 1 d . . . . .
C16A C 0.08982(17) 0.8427(2) 0.17502(13) 0.0208(4) Uani 1 1 d . . . . .
H16A H 0.009(2) 0.871(3) 0.1340(16) 0.021(6) Uiso 1 1 d . . . . .
C17A C 0.09514(17) 0.7534(2) 0.24705(13) 0.0199(4) Uani 1 1 d . . . . .
H17A H 0.018(2) 0.722(3) 0.2535(17) 0.025(6) Uiso 1 1 d . . . . .
C18A C 0.20898(16) 0.7095(2) 0.30975(12) 0.0173(3) Uani 1 1 d . . . . .
H18A H 0.212(2) 0.646(3) 0.3598(16) 0.018(6) Uiso 1 1 d . . . . .
C19A C 0.31704(16) 0.75733(19) 0.29660(11) 0.0151(3) Uani 1 1 d . . . . .
O1B O 0.67750(11) 0.00151(14) 0.17678(8) 0.0147(2) Uani 1 1 d . . . . .
H1B H 0.654(2) -0.069(3) 0.1408(18) 0.023(6) Uiso 1 1 d . . . . .
O2B O 0.43684(11) 0.00674(14) 0.06953(8) 0.0139(2) Uani 1 1 d . . . . .
H2B H 0.447(3) -0.032(3) 0.120(2) 0.033(7) Uiso 1 1 d . . . . .
O3B O 0.37738(12) 0.26434(14) -0.05840(8) 0.0171(3) Uani 1 1 d . . . . .
O4B O 0.90751(12) 0.46498(14) 0.23709(9) 0.0210(3) Uani 1 1 d . . . . .
N1B N 0.43188(14) 0.36634(17) 0.24710(10) 0.0156(3) Uani 1 1 d . . . . .
N2B N 0.43990(13) 0.22926(16) 0.13408(10) 0.0133(3) Uani 1 1 d . . . . .
C1B C 0.64210(15) 0.12530(19) 0.12406(11) 0.0128(3) Uani 1 1 d . . . . .
C2B C 0.49392(15) 0.13963(18) 0.08276(11) 0.0121(3) Uani 1 1 d . . . . .
C3B C 0.47097(15) 0.19918(19) -0.01316(11) 0.0144(3) Uani 1 1 d . . . . .
C4B C 0.57902(17) 0.15950(19) -0.03605(12) 0.0161(3) Uani 1 1 d . . . . .
H4B H 0.582(2) 0.167(3) -0.0986(18) 0.025(6) Uiso 1 1 d . . . . .
C5B C 0.67368(16) 0.11574(19) 0.03748(11) 0.0144(3) Uani 1 1 d . . . . .
C6B C 0.79571(17) 0.0603(2) 0.03677(13) 0.0194(4) Uani 1 1 d . . . . .
H6D H 0.793(3) 0.035(3) -0.0268(19) 0.029(7) Uiso 1 1 d . . . . .
H6E H 0.816(3) -0.025(4) 0.069(2) 0.038(8) Uiso 1 1 d . . . . .
H6F H 0.862(3) 0.123(4) 0.064(2) 0.049(9) Uiso 1 1 d . . . . .
C7B C 0.70825(15) 0.25054(19) 0.18802(11) 0.0128(3) Uani 1 1 d . . . . .
C8B C 0.70230(16) 0.38785(19) 0.13387(12) 0.0150(3) Uani 1 1 d . . . . .
H8C H 0.736(2) 0.373(3) 0.0842(17) 0.023(6) Uiso 1 1 d . . . . .
H8D H 0.614(2) 0.417(3) 0.1029(18) 0.025(6) Uiso 1 1 d . . . . .
C9B C 0.77947(17) 0.5049(2) 0.19399(12) 0.0191(4) Uani 1 1 d . . . . .
H9C H 0.780(2) 0.591(3) 0.1601(16) 0.019(6) Uiso 1 1 d . . . . .
H9D H 0.742(2) 0.530(3) 0.2406(16) 0.015(5) Uiso 1 1 d . . . . .
C10B C 0.91733(17) 0.3457(2) 0.29424(13) 0.0190(4) Uani 1 1 d . . . . .
H10C H 0.887(2) 0.368(3) 0.3423(15) 0.012(5) Uiso 1 1 d . . . . .
H10D H 1.009(2) 0.328(3) 0.3227(16) 0.018(6) Uiso 1 1 d . . . . .
C11B C 0.84815(16) 0.21779(19) 0.24124(12) 0.0162(3) Uani 1 1 d . . . . .
H11C H 0.851(2) 0.139(3) 0.2818(17) 0.020(6) Uiso 1 1 d . . . . .
H11D H 0.894(2) 0.189(3) 0.1984(17) 0.023(6) Uiso 1 1 d . . . . .
C12B C 0.64167(15) 0.2695(2) 0.25707(11) 0.0148(3) Uani 1 1 d . . . . .
H12C H 0.651(2) 0.183(3) 0.2919(16) 0.014(5) Uiso 1 1 d . . . . .
H12D H 0.678(2) 0.343(3) 0.2977(17) 0.017(6) Uiso 1 1 d . . . . .
C13B C 0.50452(15) 0.29480(18) 0.21369(11) 0.0129(3) Uani 1 1 d . . . . .
C14B C 0.30985(16) 0.3430(2) 0.18663(12) 0.0156(3) Uani 1 1 d . . . . .
C15B C 0.19482(18) 0.3892(2) 0.19033(13) 0.0202(4) Uani 1 1 d . . . . .
H15B H 0.191(2) 0.451(3) 0.2366(19) 0.029(7) Uiso 1 1 d . . . . .
C16B C 0.08662(17) 0.3454(2) 0.12225(14) 0.0219(4) Uani 1 1 d . . . . .
H16B H 0.005(2) 0.376(3) 0.1232(16) 0.023(6) Uiso 1 1 d . . . . .
C17B C 0.09074(16) 0.2576(2) 0.05195(12) 0.0195(4) Uani 1 1 d . . . . .
H17B H 0.014(3) 0.227(3) 0.0053(19) 0.024(6) Uiso 1 1 d . . . . .
C18B C 0.20347(16) 0.2117(2) 0.04658(12) 0.0168(3) Uani 1 1 d . . . . .
H18B H 0.206(2) 0.149(3) -0.0023(16) 0.017 Uiso 1 1 d . U . . .
C19B C 0.31264(15) 0.25658(19) 0.11509(11) 0.0144(3) Uani 1 1 d . . . . .


_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
O1A H1A 0.84(3) . ?
O1A C1A 1.415(2) . ?
O2A H2A 0.91(3) . ?
O2A C2A 1.398(2) . ?
O3A C3A 1.219(2) . ?
O4A C9A 1.427(2) . ?
O4A C10A 1.429(2) . ?
N1A C13A 1.317(2) . ?
N1A C14A 1.400(2) . ?
N2A C2A 1.455(2) . ?
N2A C13A 1.364(2) . ?
N2A C19A 1.400(2) . ?
C1A C2A 1.581(2) . ?
C1A C5A 1.535(2) . ?
C1A C7A 1.569(2) . ?
C2A C3A 1.554(2) . ?
C3A C4A 1.453(2) . ?
C4A H4A 1.00(3) . ?
C4A C5A 1.334(3) . ?
C5A C6A 1.494(3) . ?
C6A H6A 1.03(3) . ?
C6A H6B 0.90(4) . ?
C6A H6C 0.99(3) . ?
C7A C8A 1.546(2) . ?
C7A C11A 1.548(2) . ?
C7A C12A 1.542(2) . ?
C8A H8A 0.99(3) . ?
C8A H8B 0.98(2) . ?
C8A C9A 1.524(3) . ?
C9A H9A 0.96(2) . ?
C9A H9B 0.99(3) . ?
C10A H10A 0.98(3) . ?
C10A H10B 0.97(3) . ?
C10A C11A 1.527(3) . ?
C11A H11A 1.00(3) . ?
C11A H11B 0.95(3) . ?
C12A H12A 0.95(3) . ?
C12A H12B 0.98(3) . ?
C12A C13A 1.489(2) . ?
C14A C15A 1.403(2) . ?
C14A C19A 1.399(2) . ?
C15A H15A 0.96(3) . ?
C15A C16A 1.385(3) . ?
C16A H16A 0.96(2) . ?
C16A C17A 1.403(3) . ?
C17A H17A 0.97(3) . ?
C17A C18A 1.389(3) . ?
C18A H18A 0.98(3) . ?
C18A C19A 1.394(2) . ?
O1B H1B 0.85(3) . ?
O1B C1B 1.414(2) . ?
O2B H2B 0.85(3) . ?
O2B C2B 1.400(2) . ?
O3B C3B 1.221(2) . ?
O4B C9B 1.425(2) . ?
O4B C10B 1.427(2) . ?
N1B C13B 1.316(2) . ?
N1B C14B 1.398(2) . ?
N2B C2B 1.453(2) . ?
N2B C13B 1.363(2) . ?
N2B C19B 1.396(2) . ?
C1B C2B 1.585(2) . ?
C1B C5B 1.536(2) . ?
C1B C7B 1.569(2) . ?
C2B C3B 1.551(2) . ?
C3B C4B 1.449(2) . ?
C4B H4B 1.00(3) . ?
C4B C5B 1.342(3) . ?
C5B C6B 1.489(2) . ?
C6B H6D 1.02(3) . ?
C6B H6E 0.95(3) . ?
C6B H6F 0.94(4) . ?
C7B C8B 1.547(2) . ?
C7B C11B 1.548(2) . ?
C7B C12B 1.543(2) . ?
C8B H8C 1.00(3) . ?
C8B H8D 0.99(3) . ?
C8B C9B 1.523(2) . ?
C9B H9C 0.98(3) . ?
C9B H9D 1.00(2) . ?
C10B H10C 0.97(2) . ?
C10B H10D 0.99(2) . ?
C10B C11B 1.526(3) . ?
C11B H11C 0.98(3) . ?
C11B H11D 1.02(3) . ?
C12B H12C 0.97(3) . ?
C12B H12D 0.94(3) . ?
C12B C13B 1.487(2) . ?
C14B C15B 1.402(2) . ?
C14B C19B 1.406(2) . ?
C15B H15B 0.95(3) . ?
C15B C16B 1.383(3) . ?
C16B H16B 0.98(3) . ?
C16B C17B 1.403(3) . ?
C17B H17B 0.97(3) . ?
C17B C18B 1.386(3) . ?
C18B H18B 0.98(3) . ?
C18B C19B 1.396(2) . ?

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
C1A O1A H1A 111.4(19) . . ?
C2A O2A H2A 111(2) . . ?
C9A O4A C10A 110.14(14) . . ?
C13A N1A C14A 104.73(14) . . ?
C13A N2A C2A 125.89(14) . . ?
C13A N2A C19A 107.10(14) . . ?
C19A N2A C2A 126.67(14) . . ?
O1A C1A C2A 110.29(13) . . ?
O1A C1A C5A 111.49(14) . . ?
O1A C1A C7A 106.12(13) . . ?
C5A C1A C2A 100.73(13) . . ?
C5A C1A C7A 113.97(14) . . ?
C7A C1A C2A 114.33(14) . . ?
O2A C2A N2A 110.12(13) . . ?
O2A C2A C1A 111.25(14) . . ?
O2A C2A C3A 104.68(13) . . ?
N2A C2A C1A 114.57(14) . . ?
N2A C2A C3A 112.38(14) . . ?
C3A C2A C1A 103.24(13) . . ?
O3A C3A C2A 124.52(15) . . ?
O3A C3A C4A 129.29(16) . . ?
C4A C3A C2A 106.16(14) . . ?
C3A C4A H4A 122.4(16) . . ?
C5A C4A C3A 111.06(15) . . ?
C5A C4A H4A 126.5(16) . . ?
C4A C5A C1A 113.02(15) . . ?
C4A C5A C6A 124.57(16) . . ?
C6A C5A C1A 122.41(15) . . ?
C5A C6A H6A 111.1(16) . . ?
C5A C6A H6B 111(2) . . ?
C5A C6A H6C 111.3(18) . . ?
H6A C6A H6B 109(3) . . ?
H6A C6A H6C 105(3) . . ?
H6B C6A H6C 109(3) . . ?
C8A C7A C1A 111.75(13) . . ?
C8A C7A C11A 108.12(14) . . ?
C11A C7A C1A 110.31(14) . . ?
C12A C7A C1A 108.09(13) . . ?
C12A C7A C8A 110.26(14) . . ?
C12A C7A C11A 108.26(13) . . ?
C7A C8A H8A 110.6(15) . . ?
C7A C8A H8B 108.9(15) . . ?
H8A C8A H8B 109(2) . . ?
C9A C8A C7A 111.66(14) . . ?
C9A C8A H8A 109.4(15) . . ?
C9A C8A H8B 107.1(14) . . ?
O4A C9A C8A 112.09(16) . . ?
O4A C9A H9A 109.3(14) . . ?
O4A C9A H9B 109.0(17) . . ?
C8A C9A H9A 110.0(15) . . ?
C8A C9A H9B 109.4(16) . . ?
H9A C9A H9B 107(2) . . ?
O4A C10A H10A 105.1(16) . . ?
O4A C10A H10B 110.6(16) . . ?
O4A C10A C11A 111.77(15) . . ?
H10A C10A H10B 106(2) . . ?
C11A C10A H10A 111.3(16) . . ?
C11A C10A H10B 111.9(15) . . ?
C7A C11A H11A 113.1(15) . . ?
C7A C11A H11B 110.6(14) . . ?
C10A C11A C7A 112.11(15) . . ?
C10A C11A H11A 105.9(16) . . ?
C10A C11A H11B 108.4(14) . . ?
H11A C11A H11B 106(2) . . ?
C7A C12A H12A 112.8(14) . . ?
C7A C12A H12B 107.8(15) . . ?
H12A C12A H12B 108(2) . . ?
C13A C12A C7A 113.64(13) . . ?
C13A C12A H12A 109.4(14) . . ?
C13A C12A H12B 104.6(14) . . ?
N1A C13A N2A 113.22(15) . . ?
N1A C13A C12A 126.79(15) . . ?
N2A C13A C12A 119.70(15) . . ?
N1A C14A C15A 129.43(17) . . ?
C19A C14A N1A 110.41(15) . . ?
C19A C14A C15A 120.13(16) . . ?
C14A C15A H15A 122.1(16) . . ?
C16A C15A C14A 117.50(18) . . ?
C16A C15A H15A 120.4(16) . . ?
C15A C16A H16A 119.9(15) . . ?
C15A C16A C17A 121.69(17) . . ?
C17A C16A H16A 118.4(15) . . ?
C16A C17A H17A 119.4(16) . . ?
C18A C17A C16A 121.48(17) . . ?
C18A C17A H17A 119.1(16) . . ?
C17A C18A H18A 121.1(14) . . ?
C17A C18A C19A 116.52(17) . . ?
C19A C18A H18A 122.4(14) . . ?
C14A C19A N2A 104.49(15) . . ?
C18A C19A N2A 132.79(17) . . ?
C18A C19A C14A 122.65(16) . . ?
C1B O1B H1B 107.3(18) . . ?
C2B O2B H2B 110(2) . . ?
C9B O4B C10B 110.58(14) . . ?
C13B N1B C14B 104.93(14) . . ?
C13B N2B C2B 125.83(14) . . ?
C13B N2B C19B 107.15(14) . . ?
C19B N2B C2B 126.88(14) . . ?
O1B C1B C2B 110.77(13) . . ?
O1B C1B C5B 111.63(14) . . ?
O1B C1B C7B 106.07(13) . . ?
C5B C1B C2B 100.83(13) . . ?
C5B C1B C7B 114.13(14) . . ?
C7B C1B C2B 113.54(13) . . ?
O2B C2B N2B 110.16(13) . . ?
O2B C2B C1B 110.78(14) . . ?
O2B C2B C3B 105.83(13) . . ?
N2B C2B C1B 114.76(13) . . ?
N2B C2B C3B 111.97(14) . . ?
C3B C2B C1B 102.79(13) . . ?
O3B C3B C2B 124.59(15) . . ?
O3B C3B C4B 128.87(16) . . ?
C4B C3B C2B 106.53(14) . . ?
C3B C4B H4B 123.7(15) . . ?
C5B C4B C3B 110.93(15) . . ?
C5B C4B H4B 125.3(15) . . ?
C4B C5B C1B 112.61(15) . . ?
C4B C5B C6B 124.68(16) . . ?
C6B C5B C1B 122.69(15) . . ?
C5B C6B H6D 112.4(15) . . ?
C5B C6B H6E 110.1(18) . . ?
C5B C6B H6F 112(2) . . ?
H6D C6B H6E 105(2) . . ?
H6D C6B H6F 110(3) . . ?
H6E C6B H6F 107(3) . . ?
C8B C7B C1B 111.31(13) . . ?
C8B C7B C11B 107.78(14) . . ?
C11B C7B C1B 111.47(14) . . ?
C12B C7B C1B 107.44(13) . . ?
C12B C7B C8B 110.92(14) . . ?
C12B C7B C11B 107.88(13) . . ?
C7B C8B H8C 111.1(16) . . ?
C7B C8B H8D 110.4(16) . . ?
H8C C8B H8D 105(2) . . ?
C9B C8B C7B 111.44(14) . . ?
C9B C8B H8C 107.5(15) . . ?
C9B C8B H8D 111.6(16) . . ?
O4B C9B C8B 111.85(15) . . ?
O4B C9B H9C 106.4(14) . . ?
O4B C9B H9D 110.0(13) . . ?
C8B C9B H9C 112.3(15) . . ?
C8B C9B H9D 109.1(14) . . ?
H9C C9B H9D 107(2) . . ?
O4B C10B H10C 110.7(14) . . ?
O4B C10B H10D 104.9(15) . . ?
O4B C10B C11B 111.89(15) . . ?
H10C C10B H10D 107.2(19) . . ?
C11B C10B H10C 110.3(14) . . ?
C11B C10B H10D 111.7(15) . . ?
C7B C11B H11C 107.5(14) . . ?
C7B C11B H11D 111.0(14) . . ?
C10B C11B C7B 111.82(15) . . ?
C10B C11B H11C 110.8(15) . . ?
C10B C11B H11D 107.1(15) . . ?
H11C C11B H11D 109(2) . . ?
C7B C12B H12C 108.5(14) . . ?
C7B C12B H12D 111.1(15) . . ?
H12C C12B H12D 108(2) . . ?
C13B C12B C7B 112.99(14) . . ?
C13B C12B H12C 106.8(14) . . ?
C13B C12B H12D 109.5(15) . . ?
N1B C13B N2B 113.25(15) . . ?
N1B C13B C12B 127.21(15) . . ?
N2B C13B C12B 119.27(15) . . ?
N1B C14B C15B 129.77(17) . . ?
N1B C14B C19B 110.06(15) . . ?
C15B C14B C19B 120.15(16) . . ?
C14B C15B H15B 121.7(16) . . ?
C16B C15B C14B 117.57(18) . . ?
C16B C15B H15B 120.7(16) . . ?
C15B C16B H16B 119.3(15) . . ?
C15B C16B C17B 121.67(17) . . ?
C17B C16B H16B 119.0(15) . . ?
C16B C17B H17B 120.6(16) . . ?
C18B C17B C16B 121.71(17) . . ?
C18B C17B H17B 117.6(16) . . ?
C17B C18B H18B 121.6(14) . . ?
C17B C18B C19B 116.55(17) . . ?
C19B C18B H18B 121.8(14) . . ?
N2B C19B C14B 104.57(15) . . ?
C18B C19B N2B 133.04(16) . . ?
C18B C19B C14B 122.34(15) . . ?

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
O1A H1A O3A 0.84(3) 2.02(3) 2.8592(19) 171(3) 2_646 yes
O2A H2A N1B 0.91(3) 1.87(3) 2.7677(19) 167(3) . yes
O1B H1B O3B 0.85(3) 2.00(3) 2.8507(19) 172(2) 2_645 yes
O2B H2B N1A 0.85(3) 1.95(3) 2.7864(19) 169(3) 1_545 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
O1A C1A C2A O2A 28.47(18) . . . . ?
O1A C1A C2A N2A -97.25(17) . . . . ?
O1A C1A C2A C3A 140.24(14) . . . . ?
O1A C1A C5A C4A -133.01(16) . . . . ?
O1A C1A C5A C6A 46.3(2) . . . . ?
O1A C1A C7A C8A -165.88(13) . . . . ?
O1A C1A C7A C11A -45.57(17) . . . . ?
O1A C1A C7A C12A 72.62(16) . . . . ?
O2A C2A C3A O3A -84.4(2) . . . . ?
O2A C2A C3A C4A 93.79(15) . . . . ?
O3A C3A C4A C5A -168.19(19) . . . . ?
O4A C10A C11A C7A 56.3(2) . . . . ?
N1A C14A C15A C16A 176.98(19) . . . . ?
N1A C14A C19A N2A 0.71(19) . . . . ?
N1A C14A C19A C18A -176.72(17) . . . . ?
N2A C2A C3A O3A 35.1(2) . . . . ?
N2A C2A C3A C4A -146.70(15) . . . . ?
C1A C2A C3A O3A 159.10(17) . . . . ?
C1A C2A C3A C4A -22.73(18) . . . . ?
C1A C7A C8A C9A 170.93(14) . . . . ?
C1A C7A C11A C10A -171.66(14) . . . . ?
C1A C7A C12A C13A 54.08(19) . . . . ?
C2A N2A C13A N1A 175.97(15) . . . . ?
C2A N2A C13A C12A 1.8(3) . . . . ?
C2A N2A C19A C14A -175.32(16) . . . . ?
C2A N2A C19A C18A 1.7(3) . . . . ?
C2A C1A C5A C4A -16.0(2) . . . . ?
C2A C1A C5A C6A 163.33(16) . . . . ?
C2A C1A C7A C8A 72.33(17) . . . . ?
C2A C1A C7A C11A -167.35(14) . . . . ?
C2A C1A C7A C12A -49.17(18) . . . . ?
C2A C3A C4A C5A 13.8(2) . . . . ?
C3A C4A C5A C1A 1.8(2) . . . . ?
C3A C4A C5A C6A -177.48(17) . . . . ?
C5A C1A C2A O2A -89.41(15) . . . . ?
C5A C1A C2A N2A 144.88(14) . . . . ?
C5A C1A C2A C3A 22.36(17) . . . . ?
C5A C1A C7A C8A -42.80(19) . . . . ?
C5A C1A C7A C11A 77.52(17) . . . . ?
C5A C1A C7A C12A -164.30(14) . . . . ?
C7A C1A C2A O2A 147.94(13) . . . . ?
C7A C1A C2A N2A 22.2(2) . . . . ?
C7A C1A C2A C3A -100.29(15) . . . . ?
C7A C1A C5A C4A 106.88(17) . . . . ?
C7A C1A C5A C6A -73.8(2) . . . . ?
C7A C8A C9A O4A -57.2(2) . . . . ?
C7A C12A C13A N1A 154.45(17) . . . . ?
C7A C12A C13A N2A -32.2(2) . . . . ?
C8A C7A C11A C10A -49.18(19) . . . . ?
C8A C7A C12A C13A -68.34(19) . . . . ?
C9A O4A C10A C11A -61.3(2) . . . . ?
C10A O4A C9A C8A 61.93(19) . . . . ?
C11A C7A C8A C9A 49.35(19) . . . . ?
C11A C7A C12A C13A 173.57(15) . . . . ?
C12A C7A C8A C9A -68.83(18) . . . . ?
C12A C7A C11A C10A 70.26(19) . . . . ?
C13A N1A C14A C15A -177.32(19) . . . . ?
C13A N1A C14A C19A 0.6(2) . . . . ?
C13A N2A C2A O2A -123.24(17) . . . . ?
C13A N2A C2A C1A 3.1(2) . . . . ?
C13A N2A C2A C3A 120.49(17) . . . . ?
C13A N2A C19A C14A -1.73(19) . . . . ?
C13A N2A C19A C18A 175.32(19) . . . . ?
C14A N1A C13A N2A -1.8(2) . . . . ?
C14A N1A C13A C12A 171.92(17) . . . . ?
C14A C15A C16A C17A -0.6(3) . . . . ?
C15A C14A C19A N2A 178.87(16) . . . . ?
C15A C14A C19A C18A 1.4(3) . . . . ?
C15A C16A C17A C18A 1.4(3) . . . . ?
C16A C17A C18A C19A -0.8(3) . . . . ?
C17A C18A C19A N2A -177.23(19) . . . . ?
C17A C18A C19A C14A -0.6(3) . . . . ?
C19A N2A C2A O2A 49.2(2) . . . . ?
C19A N2A C2A C1A 175.51(15) . . . . ?
C19A N2A C2A C3A -67.1(2) . . . . ?
C19A N2A C13A N1A 2.3(2) . . . . ?
C19A N2A C13A C12A -171.90(15) . . . . ?
C19A C14A C15A C16A -0.8(3) . . . . ?
O1B C1B C2B O2B -28.95(18) . . . . ?
O1B C1B C2B N2B 96.57(17) . . . . ?
O1B C1B C2B C3B -141.61(14) . . . . ?
O1B C1B C5B C4B 134.41(16) . . . . ?
O1B C1B C5B C6B -44.2(2) . . . . ?
O1B C1B C7B C8B 167.10(13) . . . . ?
O1B C1B C7B C11B 46.72(17) . . . . ?
O1B C1B C7B C12B -71.28(15) . . . . ?
O2B C2B C3B O3B 86.4(2) . . . . ?
O2B C2B C3B C4B -92.58(15) . . . . ?
O3B C3B C4B C5B 166.73(19) . . . . ?
O4B C10B C11B C7B -56.4(2) . . . . ?
N1B C14B C15B C16B -177.50(19) . . . . ?
N1B C14B C19B N2B -0.3(2) . . . . ?
N1B C14B C19B C18B 177.47(16) . . . . ?
N2B C2B C3B O3B -33.6(2) . . . . ?
N2B C2B C3B C4B 147.38(14) . . . . ?
C1B C2B C3B O3B -157.33(17) . . . . ?
C1B C2B C3B C4B 23.68(17) . . . . ?
C1B C7B C8B C9B -173.26(13) . . . . ?
C1B C7B C11B C10B 172.64(14) . . . . ?
C1B C7B C12B C13B -56.95(19) . . . . ?
C2B N2B C13B N1B -178.07(16) . . . . ?
C2B N2B C13B C12B -3.5(3) . . . . ?
C2B N2B C19B C14B 177.27(16) . . . . ?
C2B N2B C19B C18B -0.1(3) . . . . ?
C2B C1B C5B C4B 16.76(19) . . . . ?
C2B C1B C5B C6B -161.90(16) . . . . ?
C2B C1B C7B C8B -71.03(17) . . . . ?
C2B C1B C7B C11B 168.59(13) . . . . ?
C2B C1B C7B C12B 50.59(18) . . . . ?
C2B C3B C4B C5B -14.3(2) . . . . ?
C3B C4B C5B C1B -2.0(2) . . . . ?
C3B C4B C5B C6B 176.59(17) . . . . ?
C5B C1B C2B O2B 89.34(15) . . . . ?
C5B C1B C2B N2B -145.14(14) . . . . ?
C5B C1B C2B C3B -23.32(16) . . . . ?
C5B C1B C7B C8B 43.78(19) . . . . ?
C5B C1B C7B C11B -76.60(18) . . . . ?
C5B C1B C7B C12B 165.40(14) . . . . ?
C7B C1B C2B O2B -148.16(13) . . . . ?
C7B C1B C2B N2B -22.6(2) . . . . ?
C7B C1B C2B C3B 99.18(15) . . . . ?
C7B C1B C5B C4B -105.33(17) . . . . ?
C7B C1B C5B C6B 76.0(2) . . . . ?
C7B C8B C9B O4B 57.69(19) . . . . ?
C7B C12B C13B N1B -151.23(17) . . . . ?
C7B C12B C13B N2B 35.1(2) . . . . ?
C8B C7B C11B C10B 50.21(19) . . . . ?
C8B C7B C12B C13B 64.92(19) . . . . ?
C9B O4B C10B C11B 60.72(19) . . . . ?
C10B O4B C9B C8B -61.50(19) . . . . ?
C11B C7B C8B C9B -50.73(18) . . . . ?
C11B C7B C12B C13B -177.25(15) . . . . ?
C12B C7B C8B C9B 67.16(18) . . . . ?
C12B C7B C11B C10B -69.63(19) . . . . ?
C13B N1B C14B C15B 177.35(19) . . . . ?
C13B N1B C14B C19B -0.9(2) . . . . ?
C13B N2B C2B O2B 123.30(17) . . . . ?
C13B N2B C2B C1B -2.5(2) . . . . ?
C13B N2B C2B C3B -119.22(17) . . . . ?
C13B N2B C19B C14B 1.37(18) . . . . ?
C13B N2B C19B C18B -176.04(19) . . . . ?
C14B N1B C13B N2B 1.9(2) . . . . ?
C14B N1B C13B C12B -172.13(17) . . . . ?
C14B C15B C16B C17B 0.3(3) . . . . ?
C15B C14B C19B N2B -178.76(16) . . . . ?
C15B C14B C19B C18B -1.0(3) . . . . ?
C15B C16B C17B C18B -0.8(3) . . . . ?
C16B C17B C18B C19B 0.5(3) . . . . ?
C17B C18B C19B N2B 177.47(18) . . . . ?
C17B C18B C19B C14B 0.4(3) . . . . ?
C19B N2B C2B O2B -51.9(2) . . . . ?
C19B N2B C2B C1B -177.71(15) . . . . ?
C19B N2B C2B C3B 65.6(2) . . . . ?
C19B N2B C13B N1B -2.1(2) . . . . ?
C19B N2B C13B C12B 172.41(15) . . . . ?
C19B C14B C15B C16B 0.6(3) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.662
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C6UV-CDI
_database_code_depnum_ccdc_archive 'CCDC 2233465'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_audit_creation_date             2022-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H20 N2 O4'
_chemical_oxdiff_usercomment     C6UV-CDI
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.48251(7)
_cell_length_b                   8.97191(13)
_cell_length_c                   13.67021(19)
_cell_angle_alpha                107.8011(13)
_cell_angle_beta                 96.7797(9)
_cell_angle_gamma                98.0759(10)
_cell_volume                     852.40(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.0000
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 0 0.1173
0 2 7 0.0466
0 -2 -7 0.0466
0 0 8 0.0410
0 -3 9 0.0503
4 -2 2 0.1190
0 -6 4 0.0684
0 -4 -5 0.0500
5 -2 -2 0.1209
-5 3 2 0.1541
4 0 -4 0.1122
-4 0 4 0.1423
0 1 -9 0.0369
0 6 -2 0.0783
4 0 2 0.1129
-4 0 -2 0.1424
-4 -2 0 0.1453

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
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
2.0015 0.9997 -0.0027 -0.1260 0.1878 0.4357
0.0009 2.0035 6.9946 -0.9995 -0.0466 0.2071
-0.0020 -2.0054 -6.9919 0.9994 0.0462 -0.2073
0.0052 -0.0023 7.9790 -0.8630 -0.3664 0.1995
0.0009 -2.9979 9.0003 -0.6106 -0.8236 0.1747
4.0024 -2.0001 2.0076 0.0146 -0.2646 0.8556
-0.0038 -5.9910 3.9864 0.2944 -1.0035 -0.0002
-0.0006 -4.0034 -4.9931 1.0251 -0.3191 -0.1901
4.9933 -2.0008 -1.9994 0.4456 -0.0557 0.9635
-4.9990 3.0030 2.0161 -0.5688 0.1920 -0.9478
4.0037 -0.0144 -3.9924 0.4232 0.2828 0.7393
-4.0034 0.0063 3.9862 -0.4216 -0.2836 -0.7395
0.0085 0.9885 -9.0021 0.8542 0.5487 -0.2058
-0.0029 6.0039 -2.0021 -0.5106 0.9141 0.0484
4.0038 0.0017 1.9737 -0.2242 0.0112 0.8879
-4.0006 -0.0053 -1.9933 0.2268 -0.0107 -0.8878
-4.0047 -1.9967 -0.0105 0.2535 -0.3745 -0.8721

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.456
_diffrn_reflns_theta_min         3.446
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    133.00 159.00   0.40    0.33    --  111.50  45.00-180.00   65
  2  ω    101.00 177.00   0.40    0.33    --  111.50  45.00-120.00  190
  3  ω    149.00 175.00   0.40    0.33    --  111.50  45.00 -90.00   65
  4  ω    102.00 142.00   0.40    0.33    --  111.50  61.00  30.00  100
  5  ω    101.00 152.20   0.40    0.33    --  111.50  45.00  90.00  128
  6  ω    118.00 153.20   0.40    0.33    --  111.50  45.00 150.00   88
  7  ω    101.00 177.00   0.40    0.33    --  111.50  45.00 120.00  190
  8  ω    101.00 177.00   0.40    0.33    --  111.50  15.00  60.00  190
  9  ω    103.00 175.00   0.40    0.33    --  111.50  21.00  -8.03  180
 10  ω    101.00 177.00   0.40    0.33    --  111.50  15.00-120.00  190
 11  ω    124.00 150.00   0.40    0.33    --  111.50  15.00-150.00   65
 12  ω    -63.00  23.00   0.40    0.08    --  -48.76  57.00  60.00  215
 13  ω    -26.00  26.00   0.40    0.08    --  -48.76  19.00-180.00  130
 14  ω    -26.00  26.00   0.40    0.08    --  -48.76  19.00 -90.00  130
 15  ω    -51.00 -19.00   0.40    0.33    --  -90.00  45.00   0.00   80
 16  ω    -43.00  23.00   0.40    0.08    --  -48.76  38.00 150.00  165
 17  ω     40.00 110.00   0.40    0.33    --  111.50-125.00 -60.00  175
 18  ω     82.00 108.00   0.40    0.33    --  111.50-119.00  42.62   65
 19  ω     40.00 110.00   0.40    0.33    --  111.50-125.00   0.00  175
 20  ω     44.00  70.00   0.40    0.33    --  111.50-119.00  42.62   65
 21  ω     40.00  86.00   0.40    0.33    --  111.50-125.00 -30.00  115
 22  ω     43.00  68.20   0.40    0.33    --  111.50-104.00 -64.50   63
 23  ω     40.00 108.00   0.40    0.33    --  111.50-110.00 -24.00  170
 24  ω     63.00 103.00   0.40    0.33    --  111.50-103.00  31.48  100
 25  ω     23.00  87.00   0.40    0.08    --   48.76-110.00 -24.00  160
 26  ω     40.00 104.00   0.40    0.33    --  111.50 -98.00  61.25  160
 27  ω     72.00  98.00   0.40    0.33    --  111.50-104.00 -64.50   65
 28  ω     61.00  92.20   0.40    0.33    --  111.50 -95.00-120.00   78
 29  ω     40.00 110.00   0.40    0.33    --  111.50-125.00-180.00  175
 30  ω     76.00 102.00   0.40    0.33    --  111.50-102.00-168.32   65
 31  ω     84.00 109.20   0.40    0.33    --  111.50-125.00 -90.00   63
 32  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00-180.00  160
 33  ω     44.00  78.00   0.40    0.33    --  111.50 -95.00   0.00   85
 34  ω     76.00 103.20   0.40    0.33    --  111.50 -95.00 -30.00   68
 35  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00  30.00  160
 36  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00  60.00  160
 37  ω     45.00 103.00   0.40    0.33    --  111.50 -95.00 150.00  145
 38  ω     40.00  76.00   0.40    0.33    --  111.50 -95.00  90.00   90
 39  ω     42.00  69.20   0.40    0.33    --  111.50 -85.00  64.61   68
 40  ω     40.00  65.20   0.40    0.33    --  111.50 -87.00 -83.52   63
 41  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00-150.00  160
 42  ω    103.00 129.00   0.40    0.33    --  111.50 -87.00 -83.52   65
 43  ω     84.00 116.00   0.40    0.33    --  111.50 -85.00  64.61   80
 44  ω     59.00 104.20   0.40    0.33    --  111.50 -77.00  60.00  113
 45  ω     65.00  99.00   0.40    0.33    --  111.50 -77.00 150.00   85
 46  ω     50.00  94.00   0.40    0.33    --  111.50 -77.00 -30.00  110
 47  ω     40.00  70.00   0.40    0.33    --  111.50 -61.00-180.00   75
 48  ω     57.00  99.00   0.40    0.33    --  111.50 -77.00-180.00  105
 49  ω     45.00  71.00   0.40    0.33    --  111.50 -77.00 -90.00   65
 50  ω    -25.00  25.00   0.40    0.08    --   48.76 -19.00 -90.00  125
 51  ω     44.00  69.20   0.40    0.33    --  111.50 -61.00 120.00   63
 52  ω     42.00  70.00   0.40    0.33    --  111.50 -61.00 150.00   70
 53  ω     95.00 177.00   0.40    0.33    --  111.50 125.00 -60.00  205
 54  ω    138.00 170.00   0.40    0.33    --  111.50 125.00   0.00   80
 55  ω    102.00 127.20   0.40    0.33    --  111.50 125.00   0.00   63
 56  ω    122.00 148.00   0.40    0.33    --  111.50 125.00-120.00   65
 57  ω     96.00 121.20   0.40    0.33    --  111.50 125.00-120.00   63
 58  ω     97.00 151.00   0.40    0.33    --  111.50 125.00-150.00  135
 59  ω    124.00 170.00   0.40    0.33    --  111.50 125.00 -90.00  115
 60  ω    103.00 177.00   0.40    0.33    --  111.50 110.00  70.00  185
 61  ω    131.00 167.00   0.40    0.33    --  111.50 125.00 150.00   90
 62  ω   -161.00 -77.00   0.40    0.33    --  -90.00 -56.00  49.09  210
 63  ω   -121.00 -73.00   0.40    0.08    --  -48.76-125.00 150.00  120
 64  ω   -121.00 -73.00   0.40    0.08    --  -48.76-125.00  30.00  120
 65  ω   -161.00 -83.00   0.40    0.33    --  -90.00-110.00 -24.00  195
 66  ω    -82.00 -18.00   0.40    0.33    --  -90.00 110.00  70.00  160
 67  ω    -82.00  -2.00   0.40    0.08    --  -48.76 110.00  70.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0026200000
_diffrn_orient_matrix_UB_12      -0.1211283000
_diffrn_orient_matrix_UB_13      -0.1081933000
_diffrn_orient_matrix_UB_21      0.0253528000
_diffrn_orient_matrix_UB_22      0.1369548000
_diffrn_orient_matrix_UB_23      -0.0458929000
_diffrn_orient_matrix_UB_31      0.2095069000
_diffrn_orient_matrix_UB_32      0.0164490000
_diffrn_orient_matrix_UB_33      0.0248681000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3503
_reflns_number_total             3679
_reflns_odcompleteness_completeness 98.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0025(7)
_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   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.034
_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)+(0.0621P)²+0.3236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.30972(11) 0.14207(9) 0.56007(6) 0.01931(19) Uani 1 1 d . . . . .
O2 O 0.16873(11) 0.34055(9) 0.54728(6) 0.01853(19) Uani 1 1 d . . . . .
O3 O 0.08467(12) 0.09833(10) 0.42475(7) 0.0246(2) Uani 1 1 d . . . . .
O4 O 0.39287(13) 0.67360(10) 0.63279(8) 0.0282(2) Uani 1 1 d . . . . .
N1 N 0.05468(13) 0.41373(11) 0.86205(7) 0.0181(2) Uani 1 1 d . . . . .
N2 N 0.18665(12) 0.45191(11) 0.72947(7) 0.0161(2) Uani 1 1 d . . . . .
C1 C 0.17933(15) 0.18475(13) 0.50330(9) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.29081(15) 0.40976(13) 0.64716(8) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.40585(15) 0.27725(12) 0.64931(9) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.42969(16) 0.54881(13) 0.63769(9) 0.0196(2) Uani 1 1 d . . . . .
C5 C 0.59995(16) 0.49167(14) 0.62455(9) 0.0219(2) Uani 1 1 d . . . . .
H5 H 0.703(2) 0.556(2) 0.6130(13) 0.030(4) Uiso 1 1 d . . . . .
C6 C 0.58828(15) 0.34091(14) 0.62363(9) 0.0200(2) Uani 1 1 d . . . . .
C7 C 0.73029(17) 0.24191(16) 0.59561(11) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.818(3) 0.295(3) 0.5609(17) 0.051(5) Uiso 1 1 d . . . . .
H7B H 0.672(2) 0.136(2) 0.5473(14) 0.036(4) Uiso 1 1 d . . . . .
H7C H 0.800(2) 0.234(2) 0.6591(15) 0.036(4) Uiso 1 1 d . . . . .
C8 C 0.41539(15) 0.22380(13) 0.74724(9) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.21853(15) 0.20422(13) 0.77032(9) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.140(2) 0.1226(18) 0.7108(12) 0.020(3) Uiso 1 1 d . . . . .
H9B H 0.209(2) 0.171(2) 0.8318(13) 0.026(4) Uiso 1 1 d . . . . .
C10 C 0.14937(14) 0.35594(13) 0.79037(8) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.02040(15) 0.55622(13) 0.84849(9) 0.0172(2) Uani 1 1 d . . . . .
C12 C -0.07578(16) 0.66415(14) 0.90652(9) 0.0200(2) Uani 1 1 d . . . . .
H12 H -0.120(2) 0.6515(19) 0.9676(13) 0.024(4) Uiso 1 1 d . . . . .
C13 C -0.10037(16) 0.79433(14) 0.87578(10) 0.0217(2) Uani 1 1 d . . . . .
H13 H -0.168(2) 0.874(2) 0.9161(13) 0.030(4) Uiso 1 1 d . . . . .
C14 C -0.03244(16) 0.81478(14) 0.78850(9) 0.0208(2) Uani 1 1 d . . . . .
H14 H -0.056(2) 0.907(2) 0.7668(13) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.06780(15) 0.71039(13) 0.73133(9) 0.0192(2) Uani 1 1 d . . . . .
H15 H 0.113(2) 0.7237(19) 0.6706(13) 0.023(4) Uiso 1 1 d . . . . .
C16 C 0.09665(14) 0.58184(13) 0.76466(8) 0.0163(2) Uani 1 1 d . . . . .
C17 C 0.47871(16) 0.06189(13) 0.72745(9) 0.0213(2) Uani 1 1 d . . . . .
H17A H 0.387(2) -0.020(2) 0.6721(13) 0.027(4) Uiso 1 1 d . . . . .
H17B H 0.597(2) 0.0633(19) 0.7012(12) 0.024(4) Uiso 1 1 d . . . . .
C18 C 0.50559(17) 0.01587(14) 0.82668(10) 0.0241(3) Uani 1 1 d . . . . .
H18A H 0.384(2) -0.0062(19) 0.8484(12) 0.025(4) Uiso 1 1 d . . . . .
H18B H 0.555(2) -0.086(2) 0.8080(13) 0.031(4) Uiso 1 1 d . . . . .
C19 C 0.63700(18) 0.14628(15) 0.91546(10) 0.0258(3) Uani 1 1 d . . . . .
H19A H 0.651(2) 0.119(2) 0.9813(14) 0.034(4) Uiso 1 1 d . . . . .
H19B H 0.762(2) 0.159(2) 0.8957(13) 0.027(4) Uiso 1 1 d . . . . .
C20 C 0.57244(17) 0.30581(14) 0.93740(9) 0.0229(3) Uani 1 1 d . . . . .
H20A H 0.665(2) 0.390(2) 0.9927(13) 0.029(4) Uiso 1 1 d . . . . .
H20B H 0.455(2) 0.302(2) 0.9672(13) 0.029(4) Uiso 1 1 d . . . . .
C21 C 0.54835(15) 0.35239(13) 0.83849(9) 0.0190(2) Uani 1 1 d . . . . .
H21A H 0.669(2) 0.3655(18) 0.8164(12) 0.020(3) Uiso 1 1 d . . . . .
H21B H 0.506(2) 0.454(2) 0.8535(12) 0.024(4) Uiso 1 1 d . . . . .


_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 C1 1.3449(14) . ?
O1 C3 1.4559(13) . ?
O2 C1 1.3602(14) . ?
O2 C2 1.4533(13) . ?
O3 C1 1.1887(14) . ?
O4 C4 1.2091(15) . ?
N1 C10 1.2990(15) . ?
N1 C11 1.4000(14) . ?
N2 C2 1.4305(14) . ?
N2 C10 1.3921(14) . ?
N2 C16 1.4134(14) . ?
C2 C3 1.5678(15) . ?
C2 C4 1.5554(15) . ?
C3 C6 1.5262(15) . ?
C3 C8 1.5514(15) . ?
C4 C5 1.4489(17) . ?
C5 H5 0.955(18) . ?
C5 C6 1.3392(17) . ?
C6 C7 1.4893(16) . ?
C7 H7A 1.01(2) . ?
C7 H7B 0.982(19) . ?
C7 H7C 0.987(19) . ?
C8 C9 1.5398(15) . ?
C8 C17 1.5464(15) . ?
C8 C21 1.5432(15) . ?
C9 H9A 0.972(15) . ?
C9 H9B 0.983(17) . ?
C9 C10 1.4829(15) . ?
C11 C12 1.3950(16) . ?
C11 C16 1.4036(15) . ?
C12 H12 0.965(17) . ?
C12 C13 1.3845(16) . ?
C13 H13 0.999(17) . ?
C13 C14 1.4023(17) . ?
C14 H14 0.991(18) . ?
C14 C15 1.3924(16) . ?
C15 H15 0.965(16) . ?
C15 C16 1.3973(15) . ?
C17 H17A 0.993(17) . ?
C17 H17B 0.994(16) . ?
C17 C18 1.5338(17) . ?
C18 H18A 1.005(16) . ?
C18 H18B 1.005(18) . ?
C18 C19 1.5282(17) . ?
C19 H19A 1.001(19) . ?
C19 H19B 1.005(17) . ?
C19 C20 1.5290(17) . ?
C20 H20A 0.999(18) . ?
C20 H20B 1.013(17) . ?
C20 C21 1.5313(16) . ?
C21 H21A 0.990(16) . ?
C21 H21B 0.980(17) . ?

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
C1 O1 C3 111.11(8) . . ?
C1 O2 C2 110.56(8) . . ?
C10 N1 C11 104.96(9) . . ?
C10 N2 C2 122.25(9) . . ?
C10 N2 C16 105.91(9) . . ?
C16 N2 C2 131.79(9) . . ?
O1 C1 O2 111.33(9) . . ?
O3 C1 O1 124.80(10) . . ?
O3 C1 O2 123.87(11) . . ?
O2 C2 C3 103.05(8) . . ?
O2 C2 C4 106.62(9) . . ?
N2 C2 O2 110.02(9) . . ?
N2 C2 C3 115.61(9) . . ?
N2 C2 C4 115.74(9) . . ?
C4 C2 C3 104.69(9) . . ?
O1 C3 C2 102.84(8) . . ?
O1 C3 C6 108.54(9) . . ?
O1 C3 C8 107.99(8) . . ?
C6 C3 C2 103.11(9) . . ?
C6 C3 C8 116.54(9) . . ?
C8 C3 C2 116.76(9) . . ?
O4 C4 C2 124.97(11) . . ?
O4 C4 C5 127.97(11) . . ?
C5 C4 C2 106.73(9) . . ?
C4 C5 H5 120.8(10) . . ?
C6 C5 C4 112.55(10) . . ?
C6 C5 H5 126.5(10) . . ?
C5 C6 C3 111.99(10) . . ?
C5 C6 C7 124.87(11) . . ?
C7 C6 C3 123.06(10) . . ?
C6 C7 H7A 108.9(12) . . ?
C6 C7 H7B 109.8(11) . . ?
C6 C7 H7C 110.1(11) . . ?
H7A C7 H7B 109.2(16) . . ?
H7A C7 H7C 108.1(16) . . ?
H7B C7 H7C 110.7(15) . . ?
C9 C8 C3 105.85(9) . . ?
C9 C8 C17 108.51(9) . . ?
C9 C8 C21 111.63(9) . . ?
C17 C8 C3 111.96(9) . . ?
C21 C8 C3 109.17(9) . . ?
C21 C8 C17 109.70(9) . . ?
C8 C9 H9A 108.6(9) . . ?
C8 C9 H9B 112.6(9) . . ?
H9A C9 H9B 107.6(13) . . ?
C10 C9 C8 111.28(9) . . ?
C10 C9 H9A 109.8(9) . . ?
C10 C9 H9B 106.9(10) . . ?
N1 C10 N2 113.78(10) . . ?
N1 C10 C9 126.50(10) . . ?
N2 C10 C9 119.72(10) . . ?
N1 C11 C16 111.00(10) . . ?
C12 C11 N1 127.64(10) . . ?
C12 C11 C16 121.36(10) . . ?
C11 C12 H12 121.6(10) . . ?
C13 C12 C11 117.64(11) . . ?
C13 C12 H12 120.7(10) . . ?
C12 C13 H13 119.6(10) . . ?
C12 C13 C14 120.74(11) . . ?
C14 C13 H13 119.7(10) . . ?
C13 C14 H14 119.1(10) . . ?
C15 C14 C13 122.33(11) . . ?
C15 C14 H14 118.6(10) . . ?
C14 C15 H15 122.2(9) . . ?
C14 C15 C16 116.58(11) . . ?
C16 C15 H15 121.2(9) . . ?
C11 C16 N2 104.24(9) . . ?
C15 C16 N2 134.49(10) . . ?
C15 C16 C11 121.20(10) . . ?
C8 C17 H17A 108.3(10) . . ?
C8 C17 H17B 111.7(9) . . ?
H17A C17 H17B 106.7(13) . . ?
C18 C17 C8 112.18(10) . . ?
C18 C17 H17A 110.8(10) . . ?
C18 C17 H17B 107.0(9) . . ?
C17 C18 H18A 109.4(9) . . ?
C17 C18 H18B 106.8(10) . . ?
H18A C18 H18B 107.9(13) . . ?
C19 C18 C17 111.70(10) . . ?
C19 C18 H18A 110.1(9) . . ?
C19 C18 H18B 110.8(10) . . ?
C18 C19 H19A 112.0(10) . . ?
C18 C19 H19B 109.3(9) . . ?
C18 C19 C20 111.11(10) . . ?
H19A C19 H19B 106.8(14) . . ?
C20 C19 H19A 108.8(10) . . ?
C20 C19 H19B 108.6(10) . . ?
C19 C20 H20A 109.3(10) . . ?
C19 C20 H20B 110.7(10) . . ?
C19 C20 C21 110.68(10) . . ?
H20A C20 H20B 105.5(13) . . ?
C21 C20 H20A 109.5(10) . . ?
C21 C20 H20B 111.0(10) . . ?
C8 C21 H21A 107.5(9) . . ?
C8 C21 H21B 110.1(9) . . ?
C20 C21 C8 112.65(9) . . ?
C20 C21 H21A 108.1(9) . . ?
C20 C21 H21B 109.8(9) . . ?
H21A C21 H21B 108.6(13) . . ?

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
O1 C3 C6 C5 118.29(11) . . . . ?
O1 C3 C6 C7 -58.71(14) . . . . ?
O1 C3 C8 C9 -70.81(10) . . . . ?
O1 C3 C8 C17 47.24(11) . . . . ?
O1 C3 C8 C21 168.91(8) . . . . ?
O2 C2 C3 O1 -10.14(10) . . . . ?
O2 C2 C3 C6 102.69(9) . . . . ?
O2 C2 C3 C8 -128.16(9) . . . . ?
O2 C2 C4 O4 70.59(14) . . . . ?
O2 C2 C4 C5 -103.27(10) . . . . ?
O4 C4 C5 C6 -173.16(12) . . . . ?
N1 C11 C12 C13 -176.96(11) . . . . ?
N1 C11 C16 N2 -2.39(12) . . . . ?
N1 C11 C16 C15 175.01(10) . . . . ?
N2 C2 C3 O1 109.92(10) . . . . ?
N2 C2 C3 C6 -137.26(9) . . . . ?
N2 C2 C3 C8 -8.10(13) . . . . ?
N2 C2 C4 O4 -52.14(16) . . . . ?
N2 C2 C4 C5 134.01(10) . . . . ?
C1 O1 C3 C2 8.00(11) . . . . ?
C1 O1 C3 C6 -100.78(10) . . . . ?
C1 O1 C3 C8 132.03(9) . . . . ?
C1 O2 C2 N2 -114.35(10) . . . . ?
C1 O2 C2 C3 9.47(11) . . . . ?
C1 O2 C2 C4 119.40(9) . . . . ?
C2 O2 C1 O1 -4.98(12) . . . . ?
C2 O2 C1 O3 174.95(11) . . . . ?
C2 N2 C10 N1 179.34(9) . . . . ?
C2 N2 C10 C9 -0.11(15) . . . . ?
C2 N2 C16 C11 -179.57(11) . . . . ?
C2 N2 C16 C15 3.5(2) . . . . ?
C2 C3 C6 C5 9.69(13) . . . . ?
C2 C3 C6 C7 -167.30(11) . . . . ?
C2 C3 C8 C9 44.38(12) . . . . ?
C2 C3 C8 C17 162.43(9) . . . . ?
C2 C3 C8 C21 -75.91(11) . . . . ?
C2 C4 C5 C6 0.45(14) . . . . ?
C3 O1 C1 O2 -2.43(12) . . . . ?
C3 O1 C1 O3 177.65(11) . . . . ?
C3 C2 C4 O4 179.36(11) . . . . ?
C3 C2 C4 C5 5.51(12) . . . . ?
C3 C8 C9 C10 -59.82(11) . . . . ?
C3 C8 C17 C18 174.69(9) . . . . ?
C3 C8 C21 C20 -177.52(9) . . . . ?
C4 C2 C3 O1 -121.50(9) . . . . ?
C4 C2 C3 C6 -8.68(11) . . . . ?
C4 C2 C3 C8 120.48(10) . . . . ?
C4 C5 C6 C3 -6.65(15) . . . . ?
C4 C5 C6 C7 170.29(11) . . . . ?
C6 C3 C8 C9 166.79(9) . . . . ?
C6 C3 C8 C17 -75.16(12) . . . . ?
C6 C3 C8 C21 46.50(12) . . . . ?
C8 C3 C6 C5 -119.60(11) . . . . ?
C8 C3 C6 C7 63.41(14) . . . . ?
C8 C9 C10 N1 -138.33(11) . . . . ?
C8 C9 C10 N2 41.04(13) . . . . ?
C8 C17 C18 C19 -54.87(13) . . . . ?
C9 C8 C17 C18 -68.86(12) . . . . ?
C9 C8 C21 C20 65.81(12) . . . . ?
C10 N1 C11 C12 -179.65(11) . . . . ?
C10 N1 C11 C16 0.65(12) . . . . ?
C10 N2 C2 O2 99.63(11) . . . . ?
C10 N2 C2 C3 -16.54(14) . . . . ?
C10 N2 C2 C4 -139.45(10) . . . . ?
C10 N2 C16 C11 3.08(11) . . . . ?
C10 N2 C16 C15 -173.80(12) . . . . ?
C11 N1 C10 N2 1.48(12) . . . . ?
C11 N1 C10 C9 -179.12(10) . . . . ?
C11 C12 C13 C14 0.78(17) . . . . ?
C12 C11 C16 N2 177.89(10) . . . . ?
C12 C11 C16 C15 -4.72(17) . . . . ?
C12 C13 C14 C15 -2.48(18) . . . . ?
C13 C14 C15 C16 0.57(17) . . . . ?
C14 C15 C16 N2 179.41(11) . . . . ?
C14 C15 C16 C11 2.95(16) . . . . ?
C16 N2 C2 O2 -77.35(13) . . . . ?
C16 N2 C2 C3 166.48(10) . . . . ?
C16 N2 C2 C4 43.57(16) . . . . ?
C16 N2 C10 N1 -3.00(12) . . . . ?
C16 N2 C10 C9 177.55(9) . . . . ?
C16 C11 C12 C13 2.72(17) . . . . ?
C17 C8 C9 C10 179.86(9) . . . . ?
C17 C8 C21 C20 -54.50(13) . . . . ?
C17 C18 C19 C20 55.64(14) . . . . ?
C18 C19 C20 C21 -55.95(14) . . . . ?
C19 C20 C21 C8 56.37(13) . . . . ?
C21 C8 C9 C10 58.85(12) . . . . ?
C21 C8 C17 C18 53.33(13) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.650
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KokBnIn-UV-Ac
_database_code_depnum_ccdc_archive 'CCDC 2233471'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H22N2O5
_chemical_oxdiff_usercomment     KokBnIn-UV-Ac
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.16824(5)
_cell_length_b                   16.10854(12)
_cell_length_c                   13.62304(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.7049(6)
_cell_angle_gamma                90
_cell_volume                     1791.71(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19730
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3410
_cell_measurement_theta_min      2.7990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -2 1 0.0613
-1 1 1 0.1619
0 1 0 0.1542
0 5 2 0.2056
0 5 -3 0.2777
5 -1 1 0.0530
-5 1 0 0.0578
0 -2 -5 0.2992
5 1 0 0.0507
-5 3 0 0.0728
-5 4 1 0.0875
-1 -5 2 0.1350
-1 -5 0 0.1866
-5 -3 3 0.0894

_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.138
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
4.9979 -2.0007 1.0008 0.2461 0.9040 0.2588
-0.9996 0.9999 0.9994 -0.0559 -0.2111 0.0923
-0.0000 0.9996 0.0001 -0.0896 -0.0052 0.0328
-0.0001 4.9982 1.9998 -0.3697 -0.0711 0.3714
0.0002 4.9983 -2.9982 -0.5660 0.0420 -0.1467
4.9979 -1.0010 1.0009 0.1565 0.8988 0.2916
-4.9979 1.0010 -0.0014 -0.1172 -0.9215 -0.1880
0.0003 -1.9992 -4.9982 -0.0170 0.1235 -0.5838
4.9979 0.9983 0.0016 -0.0620 0.9111 0.2536
-4.9979 3.0003 -0.0011 -0.2965 -0.9318 -0.1223
-4.9980 3.9999 0.9986 -0.3469 -0.9596 0.0142
-0.9997 -4.9980 1.9983 0.5212 -0.2027 -0.0011
-0.9996 -4.9979 -0.0009 0.4427 -0.1574 -0.2083
-4.9981 -2.9976 2.9969 0.3591 -0.9687 -0.0084

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.526
_diffrn_reflns_theta_min         4.251
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 136.20   0.40    0.40    --  111.50  45.00 120.00   88
  2  ω     92.00 144.00   0.40    0.40    --  111.50  77.00  90.00  130
  3  ω    146.00 177.20   0.40    0.40    --  111.50  45.00 120.00   78
  4  ω    135.00 160.20   0.40    0.40    --  111.50  61.00  30.00   63
  5  ω     97.00 131.00   0.40    0.40    --  111.50  61.00  30.00   85
  6  ω    141.00 167.00   0.40    0.40    --  111.50  30.00 150.00   65
  7  ω    150.00 175.20   0.40    0.40    --  111.50  30.00  30.00   63
  8  ω    145.00 170.20   0.40    0.40    --  111.50  30.00   0.00   63
  9  ω    112.00 146.00   0.40    0.40    --  111.50  15.00 150.00   85
 10  ω    105.00 136.20   0.40    0.40    --  111.50  30.00   0.00   78
 11  ω    148.00 177.20   0.40    0.40    --  111.50  45.00-180.00   73
 12  ω    102.00 137.20   0.40    0.40    --  111.50  45.00-180.00   88
 13  ω    -25.20  26.00   0.40    0.10    --  -48.76  19.00 150.00  128
 14  ω    -51.00 -19.00   0.40    0.40    --  -90.00  45.00-120.00   80
 15  ω    -80.00 -18.00   0.40    0.40    --  -90.00  97.00  57.00  155
 16  ω    -80.00  24.00   0.40    0.10    --  -48.76  97.00  57.00  260
 17  ω    132.00 158.00   0.40    0.40    --  111.50 125.00-150.00   65
 18  ω    102.00 128.00   0.40    0.40    --  111.50 125.00-150.00   65
 19  ω    122.00 148.00   0.40    0.40    --  111.50 125.00 -90.00   65
 20  ω    115.00 141.00   0.40    0.40    --  111.50 125.00  60.00   65
 21  ω     98.00 138.00   0.40    0.40    --  111.50 125.00 120.00  100
 22  ω    145.00 171.00   0.40    0.40    --  111.50 125.00 120.00   65
 23  ω    107.00 177.00   0.40    0.40    --  111.50  97.00  57.00  175
 24  ω     40.00  65.20   0.40    0.40    --  111.50 -61.00 150.00   63
 25  ω     48.00 104.00   0.40    0.40    --  111.50 -77.00 120.00  140
 26  ω     42.00  69.20   0.40    0.40    --  111.50 -61.00  60.00   68
 27  ω     40.00  65.20   0.40    0.40    --  111.50 -61.00  90.00   63
 28  ω     61.00  87.00   0.40    0.40    --  111.50 -77.00   0.00   65
 29  ω     41.00  67.00   0.40    0.40    --  111.50 -61.00-120.00   65
 30  ω     41.00  66.20   0.40    0.40    --  111.50 -61.00-150.00   63
 31  ω     42.00  69.20   0.40    0.40    --  111.50 -61.00 -30.00   68
 32  ω     76.80 136.00   0.40    0.40    --  111.50 -83.00   0.54  148
 33  ω     71.00  97.00   0.40    0.40    --  111.50-125.00 -30.00   65
 34  ω     40.00  69.20   0.40    0.40    --  111.50-125.00 -30.00   73
 35  ω     41.00  76.20   0.40    0.40    --  111.50-114.00 -77.37   88
 36  ω     83.00 108.20   0.40    0.40    --  111.50-114.00 -77.37   63
 37  ω     51.00  77.00   0.40    0.40    --  111.50 -98.00-161.49   65
 38  ω     54.00  84.00   0.40    0.40    --  111.50-111.00  18.71   75
 39  ω     40.00 103.20   0.40    0.40    --  111.50 -97.00 -50.00  158
 40  ω     93.00 127.00   0.40    0.40    --  111.50-151.00  53.35   85
 41  ω     88.00 114.00   0.40    0.40    --  111.50-137.00  70.41   65
 42  ω     52.00  77.20   0.40    0.40    --  111.50 -95.00 120.00   63
 43  ω     53.00  86.20   0.40    0.40    --  111.50 -95.00  60.00   83
 44  ω     50.00  76.00   0.40    0.40    --  111.50-137.00  70.41   65
 45  ω     42.00 100.00   0.40    0.40    --  111.50 -95.00 -30.00  145
 46  ω     44.00  70.00   0.40    0.40    --  111.50 -95.00 -60.00   65
 47  ω     -6.00  80.00   0.40    0.10    --   48.76 -97.00 -50.00  215
 48  ω   -117.00 -91.00   0.40    0.10    --  -48.76-125.00  30.00   65
 49  ω   -161.00 -85.00   0.40    0.40    --  -90.00 -97.00 -50.00  190
 50  ω   -121.00 -73.80   0.40    0.10    --  -48.76-125.00  60.00  118
 51  ω   -110.00 -82.80   0.40    0.10    --  -48.76-125.00 120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0054857000
_diffrn_orient_matrix_UB_12      -0.0896785000
_diffrn_orient_matrix_UB_13      0.0392619000
_diffrn_orient_matrix_UB_21      0.1833383000
_diffrn_orient_matrix_UB_22      -0.0051718000
_diffrn_orient_matrix_UB_23      -0.0226373000
_diffrn_orient_matrix_UB_31      0.0441588000
_diffrn_orient_matrix_UB_32      0.0328322000
_diffrn_orient_matrix_UB_33      0.1036756000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3770
_reflns_number_total             3879
_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 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0023(3)
_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   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.048
_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)+(0.0455P)²+0.8788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.68632(10) 0.57114(5) 0.89966(6) 0.02000(19) Uani 1 1 d . . . . .
O2 O 0.92896(11) 0.50871(7) 0.88204(9) 0.0378(3) Uani 1 1 d . . . . .
O3 O 0.65589(10) 0.40577(5) 0.99562(6) 0.02029(19) Uani 1 1 d . . . . .
O4 O 0.40591(9) 0.30928(5) 0.89167(6) 0.01591(18) Uani 1 1 d . . . . .
H4 H 0.442(2) 0.2906(12) 0.9498(14) 0.039(5) Uiso 1 1 d . . . . .
O5 O 0.98500(10) 0.24622(5) 0.76803(7) 0.02162(19) Uani 1 1 d . . . . .
N1 N 0.41967(11) 0.29285(6) 0.54865(7) 0.0155(2) Uani 1 1 d . . . . .
N2 N 0.41261(11) 0.38710(6) 0.66969(6) 0.01365(19) Uani 1 1 d . . . . .
C1 C 0.61028(13) 0.50132(7) 0.86109(8) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.60662(12) 0.42077(7) 0.91285(8) 0.0148(2) Uani 1 1 d . . . . .
C3 C 0.51851(13) 0.35877(7) 0.84287(7) 0.0131(2) Uani 1 1 d . . . . .
C4 C 0.42169(13) 0.41916(6) 0.77102(7) 0.0130(2) Uani 1 1 d . . . . .
C5 C 0.51702(13) 0.49956(7) 0.77951(8) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.4996(19) 0.5439(10) 0.7345(11) 0.023(4) Uiso 1 1 d . . . . .
C6 C 0.85372(14) 0.56712(7) 0.91037(8) 0.0189(2) Uani 1 1 d . . . . .
C7 C 0.91982(15) 0.64365(7) 0.95879(9) 0.0202(2) Uani 1 1 d . . . . .
H7A H 1.037(2) 0.6400(11) 0.9649(13) 0.035(4) Uiso 1 1 d . . . . .
H7B H 0.891(2) 0.6911(13) 0.9167(15) 0.045(5) Uiso 1 1 d . . . . .
H7C H 0.872(2) 0.6499(12) 1.0210(15) 0.044(5) Uiso 1 1 d . . . . .
C8 C 0.64427(13) 0.30234(6) 0.78815(8) 0.0135(2) Uani 1 1 d . . . . .
C9 C 0.77853(13) 0.35314(7) 0.73844(8) 0.0150(2) Uani 1 1 d . . . . .
H9A H 0.8318(18) 0.3886(9) 0.7880(11) 0.018(3) Uiso 1 1 d . . . . .
H9B H 0.7321(19) 0.3883(10) 0.6861(11) 0.021(4) Uiso 1 1 d . . . . .
C10 C 0.90792(14) 0.29732(7) 0.69472(9) 0.0186(2) Uani 1 1 d . . . . .
H10A H 0.8635(19) 0.2607(10) 0.6404(11) 0.021(4) Uiso 1 1 d . . . . .
H10B H 0.9962(19) 0.3330(10) 0.6665(11) 0.023(4) Uiso 1 1 d . . . . .
C11 C 0.86762(14) 0.19374(7) 0.81282(9) 0.0200(2) Uani 1 1 d . . . . .
H11A H 0.9290(19) 0.1619(10) 0.8624(11) 0.023(4) Uiso 1 1 d . . . . .
H11B H 0.8198(18) 0.1542(9) 0.7614(11) 0.019(3) Uiso 1 1 d . . . . .
C12 C 0.73149(14) 0.24273(7) 0.86134(8) 0.0166(2) Uani 1 1 d . . . . .
H12A H 0.6505(18) 0.2042(9) 0.8893(11) 0.019(3) Uiso 1 1 d . . . . .
H12B H 0.7790(18) 0.2743(10) 0.9184(11) 0.020(3) Uiso 1 1 d . . . . .
C13 C 0.54054(13) 0.25208(7) 0.71249(8) 0.0147(2) Uani 1 1 d . . . . .
H13A H 0.4552(19) 0.2214(10) 0.7493(11) 0.022(4) Uiso 1 1 d . . . . .
H13B H 0.605(2) 0.2130(10) 0.6742(12) 0.025(4) Uiso 1 1 d . . . . .
C14 C 0.45689(13) 0.30897(7) 0.64119(8) 0.0137(2) Uani 1 1 d . . . . .
C15 C 0.34189(13) 0.36450(7) 0.51334(8) 0.0150(2) Uani 1 1 d . . . . .
C16 C 0.27053(14) 0.38043(7) 0.42068(8) 0.0172(2) Uani 1 1 d . . . . .
H16 H 0.2714(19) 0.3400(10) 0.3705(12) 0.023(4) Uiso 1 1 d . . . . .
C17 C 0.20010(14) 0.45786(8) 0.40507(8) 0.0187(2) Uani 1 1 d . . . . .
H17 H 0.1519(18) 0.4702(10) 0.3422(11) 0.020(4) Uiso 1 1 d . . . . .
C18 C 0.20098(14) 0.51819(7) 0.47940(9) 0.0190(2) Uani 1 1 d . . . . .
H18 H 0.1515(19) 0.5732(10) 0.4663(11) 0.024(4) Uiso 1 1 d . . . . .
C19 C 0.26956(14) 0.50291(7) 0.57188(8) 0.0175(2) Uani 1 1 d . . . . .
H19 H 0.2682(19) 0.5440(10) 0.6237(12) 0.023(4) Uiso 1 1 d . . . . .
C20 C 0.33805(13) 0.42455(7) 0.58783(8) 0.0144(2) Uani 1 1 d . . . . .
C21 C 0.24716(13) 0.43410(7) 0.80593(8) 0.0162(2) Uani 1 1 d . . . . .
H21A H 0.2541(17) 0.4557(9) 0.8722(11) 0.015(3) Uiso 1 1 d . . . . .
H21B H 0.1924(18) 0.4738(10) 0.7636(11) 0.020(3) Uiso 1 1 d . . . . .
H21C H 0.1885(19) 0.3829(10) 0.8038(11) 0.022(4) Uiso 1 1 d . . . . .


_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 C1 1.3811(13) . ?
O1 C6 1.3724(14) . ?
O2 C6 1.1941(16) . ?
O3 C2 1.2102(14) . ?
O4 H4 0.89(2) . ?
O4 C3 1.3999(13) . ?
O5 C10 1.4263(14) . ?
O5 C11 1.4286(14) . ?
N1 C14 1.3140(14) . ?
N1 C15 1.3960(14) . ?
N2 C4 1.4737(13) . ?
N2 C14 1.3688(14) . ?
N2 C20 1.3921(13) . ?
C1 C2 1.4774(16) . ?
C1 C5 1.3289(16) . ?
C2 C3 1.5438(14) . ?
C3 C4 1.5760(14) . ?
C3 C8 1.5757(14) . ?
C4 C5 1.5137(14) . ?
C4 C21 1.5352(14) . ?
C5 H5 0.950(16) . ?
C6 C7 1.4918(16) . ?
C7 H7A 0.962(19) . ?
C7 H7B 0.98(2) . ?
C7 H7C 0.95(2) . ?
C8 C9 1.5411(14) . ?
C8 C12 1.5433(14) . ?
C8 C13 1.5439(14) . ?
C9 H9A 0.977(15) . ?
C9 H9B 0.978(16) . ?
C9 C10 1.5224(15) . ?
C10 H10A 1.006(16) . ?
C10 H10B 1.008(16) . ?
C11 H11A 0.975(16) . ?
C11 H11B 1.016(15) . ?
C11 C12 1.5296(16) . ?
C12 H12A 0.992(15) . ?
C12 H12B 0.998(15) . ?
C13 H13A 1.001(16) . ?
C13 H13B 0.981(17) . ?
C13 C14 1.4870(14) . ?
C15 C16 1.3983(15) . ?
C15 C20 1.4030(15) . ?
C16 H16 0.944(16) . ?
C16 C17 1.3873(16) . ?
C17 H17 0.953(15) . ?
C17 C18 1.4033(17) . ?
C18 H18 0.988(16) . ?
C18 C19 1.3855(16) . ?
C19 H19 0.968(16) . ?
C19 C20 1.3951(15) . ?
C21 H21A 0.968(15) . ?
C21 H21B 0.962(16) . ?
C21 H21C 0.953(16) . ?

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
C6 O1 C1 115.94(9) . . ?
C3 O4 H4 114.4(12) . . ?
C10 O5 C11 110.65(8) . . ?
C14 N1 C15 104.90(9) . . ?
C14 N2 C4 125.56(9) . . ?
C14 N2 C20 106.51(9) . . ?
C20 N2 C4 127.38(9) . . ?
O1 C1 C2 123.29(10) . . ?
C5 C1 O1 125.15(10) . . ?
C5 C1 C2 111.17(10) . . ?
O3 C2 C1 127.52(10) . . ?
O3 C2 C3 125.60(10) . . ?
C1 C2 C3 106.80(9) . . ?
O4 C3 C2 112.08(8) . . ?
O4 C3 C4 108.77(8) . . ?
O4 C3 C8 110.06(8) . . ?
C2 C3 C4 101.55(8) . . ?
C2 C3 C8 111.52(8) . . ?
C8 C3 C4 112.60(8) . . ?
N2 C4 C3 112.07(8) . . ?
N2 C4 C5 112.51(9) . . ?
N2 C4 C21 108.89(8) . . ?
C5 C4 C3 103.48(8) . . ?
C5 C4 C21 108.82(9) . . ?
C21 C4 C3 110.97(8) . . ?
C1 C5 C4 111.28(10) . . ?
C1 C5 H5 126.5(9) . . ?
C4 C5 H5 121.8(9) . . ?
O1 C6 C7 110.76(10) . . ?
O2 C6 O1 121.57(11) . . ?
O2 C6 C7 127.67(11) . . ?
C6 C7 H7A 109.5(11) . . ?
C6 C7 H7B 107.9(12) . . ?
C6 C7 H7C 109.2(12) . . ?
H7A C7 H7B 108.8(16) . . ?
H7A C7 H7C 111.4(15) . . ?
H7B C7 H7C 109.9(16) . . ?
C9 C8 C3 112.59(9) . . ?
C9 C8 C12 107.06(8) . . ?
C9 C8 C13 111.63(9) . . ?
C12 C8 C3 110.38(8) . . ?
C12 C8 C13 109.79(9) . . ?
C13 C8 C3 105.42(8) . . ?
C8 C9 H9A 108.3(9) . . ?
C8 C9 H9B 111.3(9) . . ?
H9A C9 H9B 108.7(12) . . ?
C10 C9 C8 111.70(9) . . ?
C10 C9 H9A 108.4(9) . . ?
C10 C9 H9B 108.4(9) . . ?
O5 C10 C9 111.35(9) . . ?
O5 C10 H10A 108.6(9) . . ?
O5 C10 H10B 106.9(9) . . ?
C9 C10 H10A 113.3(9) . . ?
C9 C10 H10B 109.0(9) . . ?
H10A C10 H10B 107.5(12) . . ?
O5 C11 H11A 105.6(9) . . ?
O5 C11 H11B 109.0(8) . . ?
O5 C11 C12 112.65(9) . . ?
H11A C11 H11B 109.1(12) . . ?
C12 C11 H11A 109.7(9) . . ?
C12 C11 H11B 110.6(8) . . ?
C8 C12 H12A 109.7(9) . . ?
C8 C12 H12B 110.3(9) . . ?
C11 C12 C8 111.68(9) . . ?
C11 C12 H12A 110.2(9) . . ?
C11 C12 H12B 109.2(9) . . ?
H12A C12 H12B 105.6(12) . . ?
C8 C13 H13A 107.6(9) . . ?
C8 C13 H13B 113.5(9) . . ?
H13A C13 H13B 109.9(13) . . ?
C14 C13 C8 110.19(9) . . ?
C14 C13 H13A 108.6(9) . . ?
C14 C13 H13B 107.0(9) . . ?
N1 C14 N2 113.47(9) . . ?
N1 C14 C13 126.42(10) . . ?
N2 C14 C13 120.11(9) . . ?
N1 C15 C16 129.49(10) . . ?
N1 C15 C20 109.91(9) . . ?
C16 C15 C20 120.58(10) . . ?
C15 C16 H16 121.0(10) . . ?
C17 C16 C15 117.59(10) . . ?
C17 C16 H16 121.4(10) . . ?
C16 C17 H17 118.9(9) . . ?
C16 C17 C18 121.25(10) . . ?
C18 C17 H17 119.9(9) . . ?
C17 C18 H18 119.8(9) . . ?
C19 C18 C17 121.76(11) . . ?
C19 C18 H18 118.4(9) . . ?
C18 C19 H19 121.9(9) . . ?
C18 C19 C20 116.86(10) . . ?
C20 C19 H19 121.2(9) . . ?
N2 C20 C15 105.19(9) . . ?
N2 C20 C19 132.90(10) . . ?
C19 C20 C15 121.91(10) . . ?
C4 C21 H21A 108.4(8) . . ?
C4 C21 H21B 109.7(9) . . ?
C4 C21 H21C 109.0(9) . . ?
H21A C21 H21B 109.5(12) . . ?
H21A C21 H21C 110.8(13) . . ?
H21B C21 H21C 109.4(13) . . ?

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
O4 H4 N1 0.89(2) 1.91(2) 2.6978(12) 146.0(17) 4_566 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
O1 C1 C2 O3 5.87(17) . . . . ?
O1 C1 C2 C3 -177.09(9) . . . . ?
O1 C1 C5 C4 -166.65(9) . . . . ?
O3 C2 C3 O4 40.84(14) . . . . ?
O3 C2 C3 C4 156.78(10) . . . . ?
O3 C2 C3 C8 -83.07(13) . . . . ?
O4 C3 C4 N2 -97.13(10) . . . . ?
O4 C3 C4 C5 141.40(8) . . . . ?
O4 C3 C4 C21 24.85(11) . . . . ?
O4 C3 C8 C9 -176.28(8) . . . . ?
O4 C3 C8 C12 -56.71(11) . . . . ?
O4 C3 C8 C13 61.79(10) . . . . ?
O5 C11 C12 C8 55.68(12) . . . . ?
N1 C15 C16 C17 179.75(11) . . . . ?
N1 C15 C20 N2 -1.07(12) . . . . ?
N1 C15 C20 C19 178.87(10) . . . . ?
N2 C4 C5 C1 -140.43(9) . . . . ?
C1 O1 C6 O2 4.63(17) . . . . ?
C1 O1 C6 C7 -176.14(10) . . . . ?
C1 C2 C3 O4 -136.26(9) . . . . ?
C1 C2 C3 C4 -20.33(10) . . . . ?
C1 C2 C3 C8 99.83(10) . . . . ?
C2 C1 C5 C4 6.34(13) . . . . ?
C2 C3 C4 N2 144.53(8) . . . . ?
C2 C3 C4 C5 23.06(10) . . . . ?
C2 C3 C4 C21 -93.50(9) . . . . ?
C2 C3 C8 C9 -51.23(11) . . . . ?
C2 C3 C8 C12 68.34(11) . . . . ?
C2 C3 C8 C13 -173.17(8) . . . . ?
C3 C4 C5 C1 -19.25(11) . . . . ?
C3 C8 C9 C10 174.38(9) . . . . ?
C3 C8 C12 C11 -173.76(9) . . . . ?
C3 C8 C13 C14 61.50(11) . . . . ?
C4 N2 C14 N1 172.71(9) . . . . ?
C4 N2 C14 C13 -8.00(16) . . . . ?
C4 N2 C20 C15 -171.55(10) . . . . ?
C4 N2 C20 C19 8.51(19) . . . . ?
C4 C3 C8 C9 62.18(11) . . . . ?
C4 C3 C8 C12 -178.25(8) . . . . ?
C4 C3 C8 C13 -59.75(11) . . . . ?
C5 C1 C2 O3 -167.27(11) . . . . ?
C5 C1 C2 C3 9.76(12) . . . . ?
C6 O1 C1 C2 66.65(14) . . . . ?
C6 O1 C1 C5 -121.18(12) . . . . ?
C8 C3 C4 N2 25.14(12) . . . . ?
C8 C3 C4 C5 -96.33(10) . . . . ?
C8 C3 C4 C21 147.12(9) . . . . ?
C8 C9 C10 O5 -59.15(12) . . . . ?
C8 C13 C14 N1 148.79(11) . . . . ?
C8 C13 C14 N2 -30.40(13) . . . . ?
C9 C8 C12 C11 -50.89(12) . . . . ?
C9 C8 C13 C14 -61.05(11) . . . . ?
C10 O5 C11 C12 -59.18(12) . . . . ?
C11 O5 C10 C9 60.54(12) . . . . ?
C12 C8 C9 C10 52.90(11) . . . . ?
C12 C8 C13 C14 -179.61(9) . . . . ?
C13 C8 C9 C10 -67.27(11) . . . . ?
C13 C8 C12 C11 70.46(11) . . . . ?
C14 N1 C15 C16 -176.95(11) . . . . ?
C14 N1 C15 C20 1.48(12) . . . . ?
C14 N2 C4 C3 10.27(14) . . . . ?
C14 N2 C4 C5 126.40(11) . . . . ?
C14 N2 C4 C21 -112.88(11) . . . . ?
C14 N2 C20 C15 0.26(11) . . . . ?
C14 N2 C20 C19 -179.68(12) . . . . ?
C15 N1 C14 N2 -1.35(12) . . . . ?
C15 N1 C14 C13 179.42(10) . . . . ?
C15 C16 C17 C18 0.26(17) . . . . ?
C16 C15 C20 N2 177.51(10) . . . . ?
C16 C15 C20 C19 -2.54(16) . . . . ?
C16 C17 C18 C19 -1.04(18) . . . . ?
C17 C18 C19 C20 0.04(17) . . . . ?
C18 C19 C20 N2 -178.34(11) . . . . ?
C18 C19 C20 C15 1.72(16) . . . . ?
C20 N2 C4 C3 -179.40(9) . . . . ?
C20 N2 C4 C5 -63.27(13) . . . . ?
C20 N2 C4 C21 57.45(13) . . . . ?
C20 N2 C14 N1 0.71(12) . . . . ?
C20 N2 C14 C13 179.99(9) . . . . ?
C20 C15 C16 C17 1.47(16) . . . . ?
C21 C4 C5 C1 98.81(10) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.586
_oxdiff_exptl_absorpt_empirical_full_min 0.390
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KOJBNIM-2
_database_code_depnum_ccdc_archive 'CCDC 2233466'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT918_KOJBNIM-2           
;
PROBLEM: Reflection(s) with I(obs) much Smaller I(calc) .         12 Check 
RESPONSE: Removing these reflections worsens the model quality.
;
_vrf_PLAT939_KOJBNIM-2           
;
PROBLEM: Large Value of Not (SHELXL) Weight Optimized S .      20.46 Check 
RESPONSE: This alert is related to alert PLAT918.
;
# end Validation Reply Form

_audit_creation_date             2022-01-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H23 N2 O3'
_chemical_oxdiff_usercomment     KOJBNIM-2
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                   11.68226(12)
_cell_length_b                   9.54123(6)
_cell_length_c                   15.99352(16)
_cell_angle_alpha                90
_cell_angle_beta                 110.8694(11)
_cell_angle_gamma                90
_cell_volume                     1665.73(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39700
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4630
_cell_measurement_theta_min      2.9540
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6684
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.481
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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     49.00  75.00   0.40    0.08    --   48.65  16.00-155.00   65
  2  ω     56.00  81.20   0.40    0.08    --   48.65  16.00-155.00   63
  3  ω     89.00 115.00   0.40    0.08    --   48.65  16.00-155.00   65
  4  ω     46.00  72.00   0.40    0.18    --  111.50 -77.00-180.00   65
  5  ω     50.00  76.00   0.40    0.18    --  111.50 -78.00-141.27   65
  6  ω     77.00 103.00   0.40    0.18    --  111.50 -77.00-180.00   65
  7  ω    104.00 130.00   0.40    0.18    --  111.50 -79.00-109.18   65
  8  ω     66.00 103.20   0.40    0.18    --  111.50 -77.00-157.28   93
  9  ω     44.00  71.20   0.40    0.18    --  111.50 -77.00-128.30   68
 10  ω     49.00  75.00   0.40    0.18    --  111.50 -79.00-109.18   65
 11  ω     59.00  85.00   0.40    0.18    --  111.50 -77.00 -30.00   65
 12  ω     61.00  99.00   0.40    0.18    --  111.50 -77.00 -60.00   95
 13  ω     54.00  79.20   0.40    0.18    --  111.50 -77.00   0.00   63
 14  ω     79.00 104.20   0.40    0.18    --  111.50 -77.00 -30.00   63
 15  ω     76.00 102.00   0.40    0.18    --  111.50 -77.00  30.00   65
 16  ω     58.00  92.00   0.40    0.18    --  111.50 -77.00  60.00   85
 17  ω     51.00  87.00   0.40    0.18    --  111.50 -77.00 120.00   90
 18  ω     40.00  66.00   0.40    0.18    --  111.50 -77.00  90.00   65
 19  ω     43.00  69.00   0.40    0.18    --  111.50 -77.00  30.00   65
 20  ω     44.00  70.00   0.40    0.18    --  111.50 -61.00  30.00   65
 21  ω     57.00  95.00   0.40    0.18    --  111.50 -77.00  60.00   95
 22  ω     40.00  65.20   0.40    0.18    --  111.50 -61.00  90.00   63
 23  ω     41.00  69.00   0.40    0.18    --  111.50 -61.00 150.00   70
 24  ω     42.00  69.20   0.40    0.18    --  111.50 -61.00 -60.00   68
 25  ω     40.00  65.20   0.40    0.18    --  111.50 -61.00 -90.00   63
 26  ω     43.00  69.00   0.40    0.18    --  111.50 -61.00 -30.00   65
 27  ω     43.00  69.00   0.40    0.18    --  111.50 -61.00-120.00   65
 28  ω     50.00  76.00   0.40    0.18    --  111.50 -77.00-180.00   65
 29  ω     40.00  67.20   0.40    0.18    --  111.50 -61.00-180.00   68
 30  ω     18.00  56.00   0.40    0.08    --   48.65 -57.00-150.00   95
 31  ω     -3.00  22.20   0.40    0.08    --   48.65 -16.00  34.00   63
 32  ω     47.00  73.00   0.40    0.18    --  111.50  -1.00 169.36   65
 33  ω     93.00 119.00   0.40    0.18    --  111.50  -1.00 169.36   65
 34  ω     93.00 119.00   0.40    0.18    --  111.50 -81.00  91.66   65
 35  ω     58.00 110.00   0.40    0.18    --  111.50-125.00  90.00  130
 36  ω     70.00 119.20   0.40    0.18    --  111.50-137.00 103.61  123
 37  ω     71.00 108.20   0.40    0.18    --  111.50-125.00  60.00   93
 38  ω     51.00  92.20   0.40    0.08    --   48.65-125.00-120.00  103
 39  ω     60.00  94.00   0.40    0.08    --   48.65-125.00-180.00   85
 40  ω     47.00  79.00   0.40    0.18    --  111.50-125.00-180.00   80
 41  ω     84.00 110.00   0.40    0.18    --  111.50-125.00-180.00   65
 42  ω     81.00 106.20   0.40    0.18    --  111.50-125.00-150.00   63
 43  ω     84.00 110.00   0.40    0.18    --  111.50-125.00 -90.00   65
 44  ω     57.00  83.00   0.40    0.18    --  111.50-125.00 -30.00   65
 45  ω     77.00 108.20   0.40    0.18    --  111.50-117.00 -87.17   78
 46  ω     45.00  71.00   0.40    0.18    --  111.50-117.00 -87.17   65
 47  ω     81.00 106.20   0.40    0.18    --  111.50-105.00 -28.94   63
 48  ω     48.00  74.00   0.40    0.18    --  111.50-118.00   9.99   65
 49  ω     48.00  80.00   0.40    0.18    --  111.50-125.00 120.00   80
 50  ω     63.00 110.20   0.40    0.18    --  111.50-125.00 150.00  118
 51  ω     82.80 108.00   0.40    0.18    --  111.50-115.00  87.02   63
 52  ω     80.80 106.00   0.40    0.18    --  111.50-100.00-104.69   63
 53  ω     69.00  94.20   0.40    0.18    --  111.50 -95.00-180.00   63
 54  ω     79.00 105.00   0.40    0.18    --  111.50 -97.00 -90.48   65
 55  ω     47.00  73.00   0.40    0.18    --  111.50 -95.00-150.00   65
 56  ω     51.00 100.20   0.40    0.18    --  111.50 -95.00 -90.00  123
 57  ω     59.00 101.00   0.40    0.18    --  111.50 -95.00 -60.00  105
 58  ω     45.00  71.00   0.40    0.18    --  111.50 -95.00   0.00   65
 59  ω     78.00 104.00   0.40    0.18    --  111.50 -95.00 -90.00   65
 60  ω     46.00  72.00   0.40    0.18    --  111.50 -95.00  60.00   65
 61  ω     74.00 100.00   0.40    0.18    --  111.50 -95.00  90.00   65
 62  ω     76.00 102.00   0.40    0.18    --  111.50 -95.00 120.00   65
 63  ω     40.00  71.20   0.40    0.18    --  111.50 -95.00 150.00   78
 64  ω    109.00 135.00   0.40    0.18    --  111.50 -88.00 -57.26   65
 65  ω     54.00  80.00   0.40    0.18    --  111.50 -88.00 -57.26   65
 66  ω     42.00  67.20   0.40    0.18    --  111.50 -95.00-120.00   63
 67  ω     57.00 104.20   0.40    0.18    --  111.50 -92.00 -77.71  118
 68  ω     87.00 113.00   0.40    0.18    --  111.50 -88.00 -22.40   65
 69  ω     64.00 122.00   0.40    0.18    --  111.50 -85.00 -67.99  145
 70  ω     54.00  80.00   0.40    0.18    --  111.50 -83.00  15.82   65
 71  ω    105.00 131.00   0.40    0.18    --  111.50 -83.00  18.70   65
 72  ω     61.00 112.20   0.40    0.18    --  111.50 -87.00 149.46  128
 73  ω     99.00 127.00   0.40    0.18    --  111.50 -87.00 174.70   70
 74  ω     84.00 110.00   0.40    0.18    --  111.50 -82.00 166.81   65
 75  ω     53.00  87.00   0.40    0.18    --  111.50 -87.00 174.70   85
 76  ω     49.00  75.00   0.40    0.18    --  111.50 -82.00 166.81   65
 77  ω    104.00 132.00   0.40    0.18    --  111.50 -81.00 104.91   70
 78  ω     74.00 100.00   0.40    0.18    --  111.50 -81.00 104.91   65
 79  ω     40.00  73.20   0.40    0.18    --  111.50 -81.00  91.66   83
 80  ω    142.00 168.00   0.40    0.18    --  111.50  15.00 -60.00   65
 81  ω     97.00 123.00   0.40    0.18    --  111.50  77.00  30.00   65
 82  ω    126.00 152.00   0.40    0.18    --  111.50  77.00 -60.00   65
 83  ω     97.00 123.00   0.40    0.18    --  111.50  77.00 -60.00   65
 84  ω     92.00 120.00   0.40    0.18    --  111.50  77.00-150.00   70
 85  ω    118.00 167.20   0.40    0.18    --  111.50  77.00-180.00  123
 86  ω    102.00 128.00   0.40    0.18    --  111.50  61.00-120.00   65
 87  ω    140.80 178.00   0.40    0.18    --  111.50  61.00  30.00   93
 88  ω    114.00 140.00   0.40    0.18    --  111.50  61.00  60.00   65
 89  ω    130.00 156.00   0.40    0.18    --  111.50  45.00  90.00   65
 90  ω    148.00 178.00   0.40    0.18    --  111.50  61.00 150.00   75
 91  ω    101.00 127.00   0.40    0.18    --  111.50  61.00 150.00   65
 92  ω    103.00 129.00   0.40    0.18    --  111.50  45.00   0.00   65
 93  ω    103.00 145.00   0.40    0.18    --  111.50  45.00 -30.00  105
 94  ω    103.00 171.00   0.40    0.18    --  111.50  45.00 -60.00  170
 95  ω    122.00 176.00   0.40    0.18    --  111.50  45.00-150.00  135
 96  ω    102.00 164.00   0.40    0.18    --  111.50  45.00 -90.00  155
 97  ω    152.00 177.20   0.40    0.18    --  111.50  45.00 -30.00   63
 98  ω    135.00 164.20   0.40    0.18    --  111.50  45.00  60.00   73
 99  ω    109.00 177.00   0.40    0.18    --  111.50  30.00  90.00  170
100  ω    102.00 128.00   0.40    0.18    --  111.50  43.00 177.98   65
101  ω    107.00 161.00   0.40    0.18    --  111.50  30.00 120.00  135
102  ω    102.00 131.20   0.40    0.18    --  111.50  15.00  90.00   73
103  ω    148.00 173.20   0.40    0.18    --  111.50  15.00 -30.00   63
104  ω    112.00 139.20   0.40    0.18    --  111.50  15.00 -60.00   68
105  ω    102.00 177.20   0.40    0.18    --  111.50  16.00-155.00  188
106  ω    138.00 163.20   0.40    0.18    --  111.50 125.00-180.00   63
107  ω    105.00 149.00   0.40    0.18    --  111.50 125.00  60.00  110
108  ω     99.00 130.20   0.40    0.18    --  111.50 125.00 120.00   78
109  ω    129.00 177.00   0.40    0.18    --  111.50 105.00 143.69  120
110  ω    -26.00  25.20   0.40    0.08    --  -48.65  19.00   0.00  128
111  ω    -24.00  15.20   0.40    0.08    --  -48.65  18.00-149.00   98
112  ω    -10.00  16.00   0.40    0.08    --  -48.65  16.00-155.00   65
113  ω    -26.00  16.00   0.40    0.08    --  -48.65  19.00-120.00  105
114  ω    -15.20  26.00   0.40    0.08    --  -48.65  19.00  90.00  103
115  ω    -51.00 -25.80   0.40    0.18    --  -90.00  45.00  30.00   63
116  ω    -51.00 -25.80   0.40    0.18    --  -90.00  45.00   0.00   63
117  ω    -51.00 -25.80   0.40    0.18    --  -90.00  45.00  90.00   63
118  ω   -121.00 -39.80   0.40    0.08    --  -48.65 -16.00  34.00  203
119  ω   -146.00-120.80   0.40    0.18    --  -90.00 -16.00  34.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1387313000
_diffrn_orient_matrix_UB_12      -0.0167027000
_diffrn_orient_matrix_UB_13      -0.0506700000
_diffrn_orient_matrix_UB_21      0.0184095000
_diffrn_orient_matrix_UB_22      0.0293818000
_diffrn_orient_matrix_UB_23      -0.0890925000
_diffrn_orient_matrix_UB_31      0.0181587000
_diffrn_orient_matrix_UB_32      -0.1578713000
_diffrn_orient_matrix_UB_33      -0.0111905000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_full    0.654
_reflns_Friedel_fraction_max     0.639
_reflns_number_gt                6666
_reflns_number_total             6684
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_coef       0.0095(13)
_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   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         6684
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.066
_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)+(0.1239P)²+0.1421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.662(3)
 0.338(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1A-H1A \\sim O2A-H2A \\sim O1B-H1B \\sim O2B-H2B
 with sigma of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C15B(H15C,H15D), C16B(H16C,H16D), C17B(H17C,H17D),
 C18B(H18C,H18D), C19B(H19C,H19D), C20B(H20C,H20D)
4.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C11A(H11A), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B), C11B(H11B)
4.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_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
O1A O 0.43238(15) 0.5090(2) 0.06588(11) 0.0136(4) Uani 1 1 d D . . . .
H1A H 0.439(3) 0.469(4) 0.1172(19) 0.016 Uiso 1 1 d D U . . .
O2A O 0.66465(15) 0.4987(2) 0.17489(11) 0.0140(4) Uani 1 1 d D . . . .
H2A H 0.635(3) 0.426(3) 0.140(2) 0.017 Uiso 1 1 d D U . . .
O3A O 0.38199(15) 0.7643(2) -0.06036(11) 0.0166(4) Uani 1 1 d . . . . .
N1A N 0.43522(18) 0.7304(2) 0.12864(13) 0.0128(4) Uani 1 1 d . . . . .
N2A N 0.42249(18) 0.8663(3) 0.23931(14) 0.0157(4) Uani 1 1 d . . . . .
C1A C 0.4957(2) 0.7955(3) 0.20833(15) 0.0131(5) Uani 1 1 d . . . . .
C2A C 0.3054(2) 0.8435(3) 0.17696(16) 0.0153(5) Uani 1 1 d . . . . .
C3A C 0.1915(2) 0.8903(3) 0.17732(17) 0.0204(6) Uani 1 1 d . . . . .
H3A H 0.185939 0.950385 0.223093 0.025 Uiso 1 1 calc R U . . .
C4A C 0.0876(2) 0.8454(4) 0.10815(18) 0.0220(6) Uani 1 1 d . . . . .
H4A H 0.009471 0.875268 0.107030 0.026 Uiso 1 1 calc R U . . .
C5A C 0.0942(2) 0.7573(3) 0.03990(17) 0.0184(5) Uani 1 1 d . . . . .
H5A H 0.020646 0.728011 -0.005792 0.022 Uiso 1 1 calc R U . . .
C6A C 0.2063(2) 0.7119(3) 0.03774(15) 0.0161(5) Uani 1 1 d . . . . .
H6A H 0.211465 0.653094 -0.008710 0.019 Uiso 1 1 calc R U . . .
C7A C 0.3104(2) 0.7571(3) 0.10722(15) 0.0134(5) Uani 1 1 d . . . . .
C8A C 0.4898(2) 0.6399(3) 0.07974(15) 0.0122(5) Uani 1 1 d . . . . .
C9A C 0.6340(2) 0.6238(3) 0.12446(15) 0.0117(5) Uani 1 1 d . . . . .
C10A C 0.6692(2) 0.6153(3) 0.04034(15) 0.0134(5) Uani 1 1 d . . . . .
C11A C 0.5792(2) 0.6591(3) -0.03385(16) 0.0160(5) Uani 1 1 d . . . . .
H11A H 0.585132 0.663532 -0.091495 0.019 Uiso 1 1 calc R U . . .
C12A C 0.4714(2) 0.6990(3) -0.01426(15) 0.0134(5) Uani 1 1 d . . . . .
C13A C 0.7906(2) 0.5624(3) 0.04367(17) 0.0187(5) Uani 1 1 d . . . . .
H13A H 0.786397 0.537933 -0.016869 0.028 Uiso 1 1 calc R U . . .
H13B H 0.812816 0.479171 0.081975 0.028 Uiso 1 1 calc R U . . .
H13C H 0.852660 0.635387 0.068100 0.028 Uiso 1 1 calc R U . . .
C14A C 0.6988(2) 0.7464(3) 0.18980(15) 0.0119(5) Uani 1 1 d . . . . .
C15A C 0.6288(2) 0.7687(3) 0.25422(15) 0.0145(5) Uani 1 1 d . . . . .
H15A H 0.639343 0.684530 0.292440 0.017 Uiso 1 1 calc R U . . .
H15B H 0.665611 0.849091 0.293819 0.017 Uiso 1 1 calc R U . . .
C16A C 0.8323(2) 0.7040(3) 0.24641(16) 0.0154(5) Uani 1 1 d . . . . .
H16A H 0.830785 0.619598 0.282020 0.018 Uiso 1 1 calc R U . . .
H16B H 0.876354 0.679672 0.205775 0.018 Uiso 1 1 calc R U . . .
C17A C 0.9017(2) 0.8214(3) 0.30972(16) 0.0179(5) Uani 1 1 d . . . . .
H17A H 0.862928 0.838871 0.354588 0.022 Uiso 1 1 calc R U . . .
H17B H 0.987239 0.791205 0.342023 0.022 Uiso 1 1 calc R U . . .
C18A C 0.9021(2) 0.9567(3) 0.25920(18) 0.0206(6) Uani 1 1 d . . . . .
H18A H 0.951329 0.943433 0.220619 0.025 Uiso 1 1 calc R U . . .
H18B H 0.940491 1.032434 0.302453 0.025 Uiso 1 1 calc R U . . .
C19A C 0.7715(2) 0.9993(3) 0.20150(17) 0.0192(5) Uani 1 1 d . . . . .
H19A H 0.726305 1.025691 0.241040 0.023 Uiso 1 1 calc R U . . .
H19B H 0.774827 1.082723 0.165614 0.023 Uiso 1 1 calc R U . . .
C20A C 0.7018(2) 0.8824(3) 0.13854(16) 0.0154(5) Uani 1 1 d . . . . .
H20A H 0.741484 0.863313 0.094362 0.018 Uiso 1 1 calc R U . . .
H20B H 0.616888 0.913697 0.105384 0.018 Uiso 1 1 calc R U . . .
O1B O 0.43045(15) 0.0105(2) 0.39611(11) 0.0137(4) Uani 1 1 d D . . . .
H1B H 0.440(3) -0.025(4) 0.348(2) 0.016 Uiso 1 1 d D U . . .
O2B O 0.66417(15) -0.0001(2) 0.40970(11) 0.0136(4) Uani 1 1 d D . . . .
H2B H 0.644(3) -0.078(3) 0.431(2) 0.016 Uiso 1 1 d D U . . .
O3B O 0.38047(15) 0.2707(2) 0.49452(12) 0.0169(4) Uani 1 1 d . . . . .
N1B N 0.43674(18) 0.2313(2) 0.33464(13) 0.0128(4) Uani 1 1 d . . . . .
N2B N 0.42938(18) 0.3697(3) 0.21987(13) 0.0147(4) Uani 1 1 d . . . . .
C1B C 0.49969(19) 0.2965(3) 0.28863(15) 0.0117(5) Uani 1 1 d . . . . .
C2B C 0.3105(2) 0.3492(3) 0.21930(16) 0.0149(5) Uani 1 1 d . . . . .
C3B C 0.1999(2) 0.4032(3) 0.15997(17) 0.0196(5) Uani 1 1 d . . . . .
H3B H 0.197532 0.463869 0.112278 0.023 Uiso 1 1 calc R U . . .
C4B C 0.0936(2) 0.3639(3) 0.17419(16) 0.0196(5) Uani 1 1 d . . . . .
H4B H 0.017043 0.399174 0.135480 0.024 Uiso 1 1 calc R U . . .
C5B C 0.0964(2) 0.2735(3) 0.24417(17) 0.0189(5) Uani 1 1 d . . . . .
H5B H 0.021585 0.248187 0.251030 0.023 Uiso 1 1 calc R U . . .
C6B C 0.2056(2) 0.2202(3) 0.30357(16) 0.0170(5) Uani 1 1 d . . . . .
H6B H 0.207716 0.158569 0.350763 0.020 Uiso 1 1 calc R U . . .
C7B C 0.3121(2) 0.2620(3) 0.29014(15) 0.0137(5) Uani 1 1 d . . . . .
C8B C 0.4884(2) 0.1413(3) 0.41197(15) 0.0114(5) Uani 1 1 d . . . . .
C9B C 0.6337(2) 0.1246(3) 0.44519(14) 0.0116(5) Uani 1 1 d . . . . .
C10B C 0.6652(2) 0.1139(3) 0.54658(15) 0.0141(5) Uani 1 1 d . . . . .
C11B C 0.5742(2) 0.1581(3) 0.57286(16) 0.0158(5) Uani 1 1 d . . . . .
H11B H 0.578056 0.160586 0.633175 0.019 Uiso 1 1 calc R U . . .
C12B C 0.4689(2) 0.2016(3) 0.49601(15) 0.0137(5) Uani 1 1 d . . . . .
C13B C 0.7857(2) 0.0605(3) 0.60881(16) 0.0185(5) Uani 1 1 d . . . . .
H13D H 0.776852 0.027432 0.664198 0.028 Uiso 1 1 calc R U . . .
H13E H 0.846436 0.136077 0.622674 0.028 Uiso 1 1 calc R U . . .
H13F H 0.812968 -0.017189 0.580343 0.028 Uiso 1 1 calc R U . . .
C14B C 0.6988(2) 0.2486(3) 0.41607(15) 0.0120(5) Uani 1 1 d . . . . .
C15B C 0.6334(2) 0.2703(3) 0.31444(14) 0.0132(5) Uani 1 1 d . . . . .
H15C H 0.671293 0.350848 0.295053 0.016 Uiso 1 1 calc R U . . .
H15D H 0.645774 0.186061 0.282548 0.016 Uiso 1 1 calc R U . . .
C16B C 0.6957(2) 0.3840(3) 0.46797(15) 0.0134(5) Uani 1 1 d . . . . .
H16C H 0.609537 0.413313 0.453689 0.016 Uiso 1 1 calc R U . . .
H16D H 0.731405 0.364885 0.533006 0.016 Uiso 1 1 calc R U . . .
C17B C 0.7667(2) 0.5032(3) 0.44491(17) 0.0172(5) Uani 1 1 d . . . . .
H17C H 0.764663 0.586555 0.481196 0.021 Uiso 1 1 calc R U . . .
H17D H 0.726121 0.528382 0.381074 0.021 Uiso 1 1 calc R U . . .
C18B C 0.9002(2) 0.4639(3) 0.46206(17) 0.0190(5) Uani 1 1 d . . . . .
H18C H 0.944164 0.450222 0.527027 0.023 Uiso 1 1 calc R U . . .
H18D H 0.940772 0.541113 0.441884 0.023 Uiso 1 1 calc R U . . .
C19B C 0.9067(2) 0.3289(3) 0.41182(17) 0.0179(5) Uani 1 1 d . . . . .
H19C H 0.873584 0.347138 0.346611 0.021 Uiso 1 1 calc R U . . .
H19D H 0.993394 0.300088 0.428310 0.021 Uiso 1 1 calc R U . . .
C20B C 0.8340(2) 0.2100(3) 0.43378(16) 0.0153(5) Uani 1 1 d . . . . .
H20C H 0.874042 0.184182 0.497566 0.018 Uiso 1 1 calc R U . . .
H20D H 0.836471 0.126926 0.397379 0.018 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
O1A H1A 0.88(3) . ?
O1A C8A 1.397(3) . ?
O2A H2A 0.88(3) . ?
O2A C9A 1.413(3) . ?
O3A C12A 1.214(3) . ?
N1A C1A 1.367(3) . ?
N1A C7A 1.398(3) . ?
N1A C8A 1.456(3) . ?
N2A C1A 1.317(3) . ?
N2A C2A 1.393(3) . ?
C1A C15A 1.487(3) . ?
C2A C3A 1.406(3) . ?
C2A C7A 1.404(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.388(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.401(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.391(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.392(3) . ?
C8A C9A 1.585(3) . ?
C8A C12A 1.547(3) . ?
C9A C10A 1.542(3) . ?
C9A C14A 1.572(3) . ?
C10A C11A 1.341(3) . ?
C10A C13A 1.489(3) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.452(3) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A C15A 1.541(3) . ?
C14A C16A 1.552(3) . ?
C14A C20A 1.542(4) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C17A 1.534(4) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17A C18A 1.524(4) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A C19A 1.530(4) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C19A C20A 1.528(4) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
O1B H1B 0.89(3) . ?
O1B C8B 1.399(3) . ?
O2B H2B 0.88(3) . ?
O2B C9B 1.417(3) . ?
O3B C12B 1.219(3) . ?
N1B C1B 1.362(3) . ?
N1B C7B 1.404(3) . ?
N1B C8B 1.449(3) . ?
N2B C1B 1.314(3) . ?
N2B C2B 1.399(3) . ?
C1B C15B 1.488(3) . ?
C2B C3B 1.401(3) . ?
C2B C7B 1.401(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.391(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.404(4) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.388(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.394(3) . ?
C8B C9B 1.596(3) . ?
C8B C12B 1.552(3) . ?
C9B C10B 1.533(3) . ?
C9B C14B 1.564(3) . ?
C10B C11B 1.342(3) . ?
C10B C13B 1.495(3) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.456(3) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B C15B 1.544(3) . ?
C14B C16B 1.543(4) . ?
C14B C20B 1.547(3) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C16B C17B 1.528(3) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.530(3) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.534(4) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C19B C20B 1.531(4) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?

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
C8A O1A H1A 111(2) . . ?
C9A O2A H2A 110(2) . . ?
C1A N1A C7A 107.04(19) . . ?
C1A N1A C8A 126.21(19) . . ?
C7A N1A C8A 126.5(2) . . ?
C1A N2A C2A 104.7(2) . . ?
N1A C1A C15A 119.0(2) . . ?
N2A C1A N1A 113.2(2) . . ?
N2A C1A C15A 127.4(2) . . ?
N2A C2A C3A 129.6(2) . . ?
N2A C2A C7A 110.6(2) . . ?
C7A C2A C3A 119.8(2) . . ?
C2A C3A H3A 121.3 . . ?
C4A C3A C2A 117.3(2) . . ?
C4A C3A H3A 121.3 . . ?
C3A C4A H4A 119.0 . . ?
C3A C4A C5A 122.1(2) . . ?
C5A C4A H4A 119.0 . . ?
C4A C5A H5A 119.4 . . ?
C6A C5A C4A 121.3(2) . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A H6A 121.8 . . ?
C5A C6A C7A 116.5(2) . . ?
C7A C6A H6A 121.8 . . ?
N1A C7A C2A 104.3(2) . . ?
C6A C7A N1A 132.7(2) . . ?
C6A C7A C2A 123.0(2) . . ?
O1A C8A N1A 109.75(19) . . ?
O1A C8A C9A 111.0(2) . . ?
O1A C8A C12A 106.20(19) . . ?
N1A C8A C9A 114.41(19) . . ?
N1A C8A C12A 111.7(2) . . ?
C12A C8A C9A 103.36(18) . . ?
O2A C9A C8A 110.6(2) . . ?
O2A C9A C10A 111.2(2) . . ?
O2A C9A C14A 106.55(18) . . ?
C10A C9A C8A 100.48(18) . . ?
C10A C9A C14A 113.83(19) . . ?
C14A C9A C8A 114.2(2) . . ?
C11A C10A C9A 112.8(2) . . ?
C11A C10A C13A 125.0(2) . . ?
C13A C10A C9A 122.2(2) . . ?
C10A C11A H11A 124.5 . . ?
C10A C11A C12A 110.9(2) . . ?
C12A C11A H11A 124.5 . . ?
O3A C12A C8A 124.7(2) . . ?
O3A C12A C11A 128.9(2) . . ?
C11A C12A C8A 106.4(2) . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15A C14A C9A 107.64(19) . . ?
C15A C14A C16A 107.93(18) . . ?
C15A C14A C20A 110.9(2) . . ?
C16A C14A C9A 109.9(2) . . ?
C20A C14A C9A 111.70(18) . . ?
C20A C14A C16A 108.7(2) . . ?
C1A C15A C14A 113.85(18) . . ?
C1A C15A H15A 108.8 . . ?
C1A C15A H15B 108.8 . . ?
C14A C15A H15A 108.8 . . ?
C14A C15A H15B 108.8 . . ?
H15A C15A H15B 107.7 . . ?
C14A C16A H16A 109.1 . . ?
C14A C16A H16B 109.1 . . ?
H16A C16A H16B 107.9 . . ?
C17A C16A C14A 112.3(2) . . ?
C17A C16A H16A 109.1 . . ?
C17A C16A H16B 109.1 . . ?
C16A C17A H17A 109.3 . . ?
C16A C17A H17B 109.3 . . ?
H17A C17A H17B 107.9 . . ?
C18A C17A C16A 111.7(2) . . ?
C18A C17A H17A 109.3 . . ?
C18A C17A H17B 109.3 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A C19A 110.7(2) . . ?
H18A C18A H18B 108.1 . . ?
C19A C18A H18A 109.5 . . ?
C19A C18A H18B 109.5 . . ?
C18A C19A H19A 109.0 . . ?
C18A C19A H19B 109.0 . . ?
H19A C19A H19B 107.8 . . ?
C20A C19A C18A 112.7(2) . . ?
C20A C19A H19A 109.0 . . ?
C20A C19A H19B 109.0 . . ?
C14A C20A H20A 109.3 . . ?
C14A C20A H20B 109.3 . . ?
C19A C20A C14A 111.81(19) . . ?
C19A C20A H20A 109.3 . . ?
C19A C20A H20B 109.3 . . ?
H20A C20A H20B 107.9 . . ?
C8B O1B H1B 107(3) . . ?
C9B O2B H2B 114(2) . . ?
C1B N1B C7B 107.0(2) . . ?
C1B N1B C8B 126.2(2) . . ?
C7B N1B C8B 126.7(2) . . ?
C1B N2B C2B 104.7(2) . . ?
N1B C1B C15B 119.3(2) . . ?
N2B C1B N1B 113.45(19) . . ?
N2B C1B C15B 127.1(2) . . ?
N2B C2B C3B 128.8(2) . . ?
N2B C2B C7B 110.5(2) . . ?
C7B C2B C3B 120.7(2) . . ?
C2B C3B H3B 121.6 . . ?
C4B C3B C2B 116.9(2) . . ?
C4B C3B H3B 121.6 . . ?
C3B C4B H4B 119.1 . . ?
C3B C4B C5B 121.8(2) . . ?
C5B C4B H4B 119.1 . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B C4B 121.7(2) . . ?
C6B C5B H5B 119.2 . . ?
C5B C6B H6B 121.8 . . ?
C5B C6B C7B 116.3(2) . . ?
C7B C6B H6B 121.8 . . ?
C2B C7B N1B 104.3(2) . . ?
C6B C7B N1B 133.1(2) . . ?
C6B C7B C2B 122.6(2) . . ?
O1B C8B N1B 110.24(19) . . ?
O1B C8B C9B 111.1(2) . . ?
O1B C8B C12B 106.06(18) . . ?
N1B C8B C9B 114.44(18) . . ?
N1B C8B C12B 112.0(2) . . ?
C12B C8B C9B 102.46(18) . . ?
O2B C9B C8B 109.84(19) . . ?
O2B C9B C10B 111.6(2) . . ?
O2B C9B C14B 107.33(18) . . ?
C10B C9B C8B 100.63(17) . . ?
C10B C9B C14B 114.0(2) . . ?
C14B C9B C8B 113.42(19) . . ?
C11B C10B C9B 113.1(2) . . ?
C11B C10B C13B 124.2(2) . . ?
C13B C10B C9B 122.7(2) . . ?
C10B C11B H11B 124.7 . . ?
C10B C11B C12B 110.5(2) . . ?
C12B C11B H11B 124.7 . . ?
O3B C12B C8B 124.7(2) . . ?
O3B C12B C11B 128.8(2) . . ?
C11B C12B C8B 106.5(2) . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C15B C14B C9B 107.71(19) . . ?
C15B C14B C20B 108.35(17) . . ?
C16B C14B C9B 111.49(18) . . ?
C16B C14B C15B 110.9(2) . . ?
C16B C14B C20B 108.6(2) . . ?
C20B C14B C9B 109.8(2) . . ?
C1B C15B C14B 113.05(18) . . ?
C1B C15B H15C 109.0 . . ?
C1B C15B H15D 109.0 . . ?
C14B C15B H15C 109.0 . . ?
C14B C15B H15D 109.0 . . ?
H15C C15B H15D 107.8 . . ?
C14B C16B H16C 109.2 . . ?
C14B C16B H16D 109.2 . . ?
H16C C16B H16D 107.9 . . ?
C17B C16B C14B 111.99(19) . . ?
C17B C16B H16C 109.2 . . ?
C17B C16B H16D 109.2 . . ?
C16B C17B H17C 109.1 . . ?
C16B C17B H17D 109.1 . . ?
C16B C17B C18B 112.4(2) . . ?
H17C C17B H17D 107.9 . . ?
C18B C17B H17C 109.1 . . ?
C18B C17B H17D 109.1 . . ?
C17B C18B H18C 109.6 . . ?
C17B C18B H18D 109.6 . . ?
C17B C18B C19B 110.4(2) . . ?
H18C C18B H18D 108.1 . . ?
C19B C18B H18C 109.6 . . ?
C19B C18B H18D 109.6 . . ?
C18B C19B H19C 109.3 . . ?
C18B C19B H19D 109.3 . . ?
H19C C19B H19D 108.0 . . ?
C20B C19B C18B 111.5(2) . . ?
C20B C19B H19C 109.3 . . ?
C20B C19B H19D 109.3 . . ?
C14B C20B H20C 108.9 . . ?
C14B C20B H20D 108.9 . . ?
C19B C20B C14B 113.3(2) . . ?
C19B C20B H20C 108.9 . . ?
C19B C20B H20D 108.9 . . ?
H20C C20B H20D 107.7 . . ?

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
O1A H1A N2B 0.88(3) 1.93(3) 2.810(3) 172(3) . yes
O2A H2A O3A 0.88(3) 1.96(3) 2.818(3) 163(3) 2_645 yes
O1B H1B N2A 0.89(3) 1.97(3) 2.833(3) 165(3) 1_545 yes
O2B H2B O3B 0.88(3) 1.96(3) 2.823(3) 166(3) 2_646 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
O1A C8A C9A O2A -26.8(3) . . . . ?
O1A C8A C9A C10A 90.7(2) . . . . ?
O1A C8A C9A C14A -146.99(18) . . . . ?
O1A C8A C12A O3A 85.9(3) . . . . ?
O1A C8A C12A C11A -93.6(2) . . . . ?
O2A C9A C10A C11A 133.1(2) . . . . ?
O2A C9A C10A C13A -46.4(3) . . . . ?
O2A C9A C14A C15A -73.2(2) . . . . ?
O2A C9A C14A C16A 44.1(2) . . . . ?
O2A C9A C14A C20A 164.80(18) . . . . ?
N1A C1A C15A C14A 34.2(3) . . . . ?
N1A C8A C9A O2A 98.1(2) . . . . ?
N1A C8A C9A C10A -144.4(2) . . . . ?
N1A C8A C9A C14A -22.1(3) . . . . ?
N1A C8A C12A O3A -33.8(4) . . . . ?
N1A C8A C12A C11A 146.8(2) . . . . ?
N2A C1A C15A C14A -152.9(3) . . . . ?
N2A C2A C3A C4A -176.7(3) . . . . ?
N2A C2A C7A N1A -1.1(3) . . . . ?
N2A C2A C7A C6A 176.9(2) . . . . ?
C1A N1A C7A C2A 1.9(3) . . . . ?
C1A N1A C7A C6A -175.8(3) . . . . ?
C1A N1A C8A O1A 123.0(2) . . . . ?
C1A N1A C8A C9A -2.5(3) . . . . ?
C1A N1A C8A C12A -119.5(3) . . . . ?
C1A N2A C2A C3A 177.9(3) . . . . ?
C1A N2A C2A C7A -0.2(3) . . . . ?
C2A N2A C1A N1A 1.5(3) . . . . ?
C2A N2A C1A C15A -171.7(3) . . . . ?
C2A C3A C4A C5A -0.3(5) . . . . ?
C3A C2A C7A N1A -179.4(2) . . . . ?
C3A C2A C7A C6A -1.4(4) . . . . ?
C3A C4A C5A C6A -0.8(5) . . . . ?
C4A C5A C6A C7A 0.8(4) . . . . ?
C5A C6A C7A N1A 177.7(3) . . . . ?
C5A C6A C7A C2A 0.3(4) . . . . ?
C7A N1A C1A N2A -2.3(3) . . . . ?
C7A N1A C1A C15A 171.6(2) . . . . ?
C7A N1A C8A O1A -50.9(3) . . . . ?
C7A N1A C8A C9A -176.4(2) . . . . ?
C7A N1A C8A C12A 66.6(3) . . . . ?
C7A C2A C3A C4A 1.3(4) . . . . ?
C8A N1A C1A N2A -177.2(2) . . . . ?
C8A N1A C1A C15A -3.4(4) . . . . ?
C8A N1A C7A C2A 176.8(2) . . . . ?
C8A N1A C7A C6A -0.9(4) . . . . ?
C8A C9A C10A C11A 16.0(3) . . . . ?
C8A C9A C10A C13A -163.5(2) . . . . ?
C8A C9A C14A C15A 49.2(3) . . . . ?
C8A C9A C14A C16A 166.52(19) . . . . ?
C8A C9A C14A C20A -72.8(2) . . . . ?
C9A C8A C12A O3A -157.2(3) . . . . ?
C9A C8A C12A C11A 23.3(3) . . . . ?
C9A C10A C11A C12A -1.6(3) . . . . ?
C9A C14A C15A C1A -55.5(3) . . . . ?
C9A C14A C16A C17A 178.30(19) . . . . ?
C9A C14A C20A C19A -176.58(19) . . . . ?
C10A C9A C14A C15A 163.9(2) . . . . ?
C10A C9A C14A C16A -78.8(2) . . . . ?
C10A C9A C14A C20A 41.9(3) . . . . ?
C10A C11A C12A O3A 166.3(3) . . . . ?
C10A C11A C12A C8A -14.3(3) . . . . ?
C12A C8A C9A O2A -140.3(2) . . . . ?
C12A C8A C9A C10A -22.7(2) . . . . ?
C12A C8A C9A C14A 99.5(2) . . . . ?
C13A C10A C11A C12A 177.9(3) . . . . ?
C14A C9A C10A C11A -106.5(2) . . . . ?
C14A C9A C10A C13A 73.9(3) . . . . ?
C14A C16A C17A C18A -56.2(3) . . . . ?
C15A C14A C16A C17A -64.6(3) . . . . ?
C15A C14A C20A C19A 63.3(3) . . . . ?
C16A C14A C15A C1A -174.0(2) . . . . ?
C16A C14A C20A C19A -55.2(3) . . . . ?
C16A C17A C18A C19A 53.7(3) . . . . ?
C17A C18A C19A C20A -54.0(3) . . . . ?
C18A C19A C20A C14A 55.9(3) . . . . ?
C20A C14A C15A C1A 67.0(3) . . . . ?
C20A C14A C16A C17A 55.8(2) . . . . ?
O1B C8B C9B O2B 28.8(2) . . . . ?
O1B C8B C9B C10B -89.0(2) . . . . ?
O1B C8B C9B C14B 148.85(18) . . . . ?
O1B C8B C12B O3B -87.8(3) . . . . ?
O1B C8B C12B C11B 91.8(2) . . . . ?
O2B C9B C10B C11B -133.1(2) . . . . ?
O2B C9B C10B C13B 47.3(3) . . . . ?
O2B C9B C14B C15B 70.8(2) . . . . ?
O2B C9B C14B C16B -167.35(17) . . . . ?
O2B C9B C14B C20B -47.0(2) . . . . ?
N1B C1B C15B C14B -34.5(3) . . . . ?
N1B C8B C9B O2B -96.9(2) . . . . ?
N1B C8B C9B C10B 145.3(2) . . . . ?
N1B C8B C9B C14B 23.2(3) . . . . ?
N1B C8B C12B O3B 32.5(4) . . . . ?
N1B C8B C12B C11B -147.9(2) . . . . ?
N2B C1B C15B C14B 151.2(3) . . . . ?
N2B C2B C3B C4B 179.0(3) . . . . ?
N2B C2B C7B N1B 0.7(3) . . . . ?
N2B C2B C7B C6B -177.7(2) . . . . ?
C1B N1B C7B C2B -1.3(3) . . . . ?
C1B N1B C7B C6B 176.8(3) . . . . ?
C1B N1B C8B O1B -124.1(2) . . . . ?
C1B N1B C8B C9B 2.0(4) . . . . ?
C1B N1B C8B C12B 118.0(3) . . . . ?
C1B N2B C2B C3B -179.9(3) . . . . ?
C1B N2B C2B C7B 0.2(3) . . . . ?
C2B N2B C1B N1B -1.1(3) . . . . ?
C2B N2B C1B C15B 173.4(3) . . . . ?
C2B C3B C4B C5B -0.5(4) . . . . ?
C3B C2B C7B N1B -179.2(2) . . . . ?
C3B C2B C7B C6B 2.5(4) . . . . ?
C3B C4B C5B C6B 0.9(5) . . . . ?
C4B C5B C6B C7B 0.4(4) . . . . ?
C5B C6B C7B N1B -179.8(3) . . . . ?
C5B C6B C7B C2B -2.0(4) . . . . ?
C7B N1B C1B N2B 1.6(3) . . . . ?
C7B N1B C1B C15B -173.4(2) . . . . ?
C7B N1B C8B O1B 52.3(3) . . . . ?
C7B N1B C8B C9B 178.4(2) . . . . ?
C7B N1B C8B C12B -65.5(3) . . . . ?
C7B C2B C3B C4B -1.1(4) . . . . ?
C8B N1B C1B N2B 178.6(2) . . . . ?
C8B N1B C1B C15B 3.6(4) . . . . ?
C8B N1B C7B C2B -178.3(2) . . . . ?
C8B N1B C7B C6B -0.2(5) . . . . ?
C8B C9B C10B C11B -16.6(3) . . . . ?
C8B C9B C10B C13B 163.8(2) . . . . ?
C8B C9B C14B C15B -50.7(3) . . . . ?
C8B C9B C14B C16B 71.1(2) . . . . ?
C8B C9B C14B C20B -168.48(18) . . . . ?
C9B C8B C12B O3B 155.6(3) . . . . ?
C9B C8B C12B C11B -24.8(3) . . . . ?
C9B C10B C11B C12B 1.2(3) . . . . ?
C9B C14B C15B C1B 56.6(3) . . . . ?
C9B C14B C16B C17B 176.00(19) . . . . ?
C9B C14B C20B C19B -176.90(19) . . . . ?
C10B C9B C14B C15B -165.08(19) . . . . ?
C10B C9B C14B C16B -43.2(3) . . . . ?
C10B C9B C14B C20B 77.2(2) . . . . ?
C10B C11B C12B O3B -164.8(3) . . . . ?
C10B C11B C12B C8B 15.7(3) . . . . ?
C12B C8B C9B O2B 141.7(2) . . . . ?
C12B C8B C9B C10B 23.9(2) . . . . ?
C12B C8B C9B C14B -98.3(2) . . . . ?
C13B C10B C11B C12B -179.2(2) . . . . ?
C14B C9B C10B C11B 105.1(2) . . . . ?
C14B C9B C10B C13B -74.5(3) . . . . ?
C14B C16B C17B C18B -56.9(3) . . . . ?
C15B C14B C16B C17B -64.0(2) . . . . ?
C15B C14B C20B C19B 65.7(3) . . . . ?
C16B C14B C15B C1B -65.7(3) . . . . ?
C16B C14B C20B C19B -54.8(3) . . . . ?
C16B C17B C18B C19B 54.9(3) . . . . ?
C17B C18B C19B C20B -53.5(3) . . . . ?
C18B C19B C20B C14B 55.3(3) . . . . ?
C20B C14B C15B C1B 175.3(2) . . . . ?
C20B C14B C16B C17B 54.9(3) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.336
_oxdiff_exptl_absorpt_empirical_full_min 0.202
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.662(3) 31812 12371 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.338(3) 0 12371 nmt -0.9998 0.0008 -0.5205 -0.0001 -1.0005 0.0010 -0.0001
0.0022 1.0001

_twin_special_details            
;
Component 2 rotated by -179.9937° 
around [-0.25 0.00 0.97] (reciprocal) or [-0.00 0.00 1.00] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C6BIMFT
_database_code_depnum_ccdc_archive 'CCDC 2233462'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT930_C6BIMFT             
;
PROBLEM: FCF-based Twin Law ( 1 0 0) Est.d BASF 0.15 Check
RESPONSE: This twin law was used in the refinement. BASF = 0.0237(7). 
;
_vrf_PLAT244_C6BIMFT             
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C21 Check 
RESPONSE: The oxygen atom O4 of the non-coordinating acetone molecule has
 a somewhat prolate thermal ellipsoid (likely due to a slight disorder of
 acetone). This problem cannot be resolved basing on the residual electron
 density.
;
_vrf_PLAT340_C6BIMFT             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00448 Ang.  
RESPONSE: This is the result of both weak diffraction power and twinning.
;
# end Validation Reply Form
_audit_creation_date             2021-10-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N2 O3, 0.5(C3 H6 O)'
_chemical_formula_sum            'C21.50 H25 N2 O3.50'
_chemical_formula_weight         367.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21.5 H25 N2 O3.5'
_chemical_oxdiff_usercomment     C6BIMFT
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.38682(16)
_cell_length_b                   12.13681(9)
_cell_length_c                   13.54889(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.0248(6)
_cell_angle_gamma                90
_cell_volume                     3676.17(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    65993
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2710
_cell_measurement_theta_min      2.0300
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            103526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.500
_diffrn_reflns_theta_min         3.266
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -90.00   0.50    0.15    --  -48.76-140.00-149.00   50
  2  ω    -75.00 -50.00   0.50    0.15    --  -48.76 140.00 -90.00   50
  3  ω   -120.00 -73.00   0.50    0.15    --  -48.76-130.00  23.00   94
  4  ω    -76.00 -48.00   0.50    0.15    --  -48.76 130.00  95.00   56
  5  ω     37.00  97.00   0.50    0.15    --   48.76-130.00  23.00  120
  6  ω     65.00 102.00   0.50    0.15    --   48.76-140.00-149.00   74
  7  ω    -83.00 -58.00   0.50    0.60    --  -90.00 140.00 -90.00   50
  8  ω   -134.00-109.00   0.50    0.60    --  -90.00-140.00-149.00   50
  9  ω   -140.00-115.00   0.50    0.60    --  -90.00-130.00  23.00   50
 10  ω    111.00 136.00   0.50    0.60    --  111.50 130.00  95.00   50
 11  ω    129.00 154.00   0.50    0.60    --  111.50 140.00 -90.00   50
 12  ω     74.00 123.00   0.50    0.60    --  111.50-140.00-149.00   98
 13  ω     63.00  93.00   0.50    0.60    --  111.50-130.00  23.00   60
 14  ω    -26.00  23.00   0.50    0.15    --  -48.76  19.00 120.00   98
 15  ω   -120.00 -81.00   0.50    0.15    --  -48.76-125.00-150.00   78
 16  ω    -26.00  17.00   0.50    0.15    --  -48.76  19.00 -60.00   86
 17  ω   -116.00 -75.00   0.50    0.15    --  -48.76-125.00  60.00   82
 18  ω   -119.00 -93.00   0.50    0.15    --  -48.76-125.00-120.00   52
 19  ω    -25.00  25.00   0.50    0.15    --  -48.76  19.00-180.00  100
 20  ω     36.00 116.00   0.50    0.15    --   48.76  57.00-180.00  160
 21  ω    -20.00  42.00   0.50    0.15    --   48.76 -38.00-120.00  124
 22  ω    -46.00 -18.00   0.50    0.60    --  -90.00  45.00 -30.00   56
 23  ω    -51.00 -18.00   0.50    0.60    --  -90.00  45.00  90.00   66
 24  ω    -48.00 -23.00   0.50    0.60    --  -90.00  45.00 120.00   50
 25  ω    127.00 154.00   0.50    0.60    --  111.50  15.00  90.00   54
 26  ω     42.00  69.00   0.50    0.60    --  111.50 -61.00-120.00   54
 27  ω    124.00 171.00   0.50    0.60    --  111.50  30.00  90.00   94
 28  ω     42.00 108.00   0.50    0.60    --  111.50-111.00-138.60  132
 29  ω     49.00  77.00   0.50    0.60    --  111.50-106.00 160.55   56
 30  ω    122.00 178.00   0.50    0.60    --  111.50  15.00 150.00  112
 31  ω     41.00  83.00   0.50    0.60    --  111.50 -77.00   0.00   84
 32  ω     63.00 105.00   0.50    0.60    --  111.50-106.00  70.66   84
 33  ω     42.00 107.00   0.50    0.60    --  111.50-103.00  92.62  130
 34  ω    144.00 169.00   0.50    0.60    --  111.50  30.00  60.00   50
 35  ω     44.00 109.00   0.50    0.60    --  111.50-116.00 -12.58  130
 36  ω     82.00 107.00   0.50    0.60    --  111.50-106.00 160.55   50
 37  ω     95.00 169.00   0.50    0.60    --  111.50 125.00 -30.00  148
 38  ω     72.00 107.00   0.50    0.60    --  111.50-105.00-114.17   70
 39  ω    132.00 158.00   0.50    0.60    --  111.50  30.00-150.00   52
 40  ω     93.00 121.00   0.50    0.60    --  111.50 -87.00   0.33   56
 41  ω     45.00  77.00   0.50    0.60    --  111.50 -77.00 -90.00   64
 42  ω     40.00  88.00   0.50    0.60    --  111.50-102.00 166.61   96
 43  ω     49.00 107.00   0.50    0.60    --  111.50-103.00 110.77  116
 44  ω    129.00 174.00   0.50    0.60    --  111.50  30.00  30.00   90
 45  ω    123.00 178.00   0.50    0.60    --  111.50  45.00-120.00  110
 46  ω    102.00 159.00   0.50    0.60    --  111.50  45.00 -90.00  114
 47  ω     44.00  69.00   0.50    0.60    --  111.50 -95.00-150.00   50
 48  ω     50.00  80.00   0.50    0.60    --  111.50-125.00 150.00   60
 49  ω    102.00 177.00   0.50    0.60    --  111.50  66.00-153.09  150
 50  ω     59.00 106.00   0.50    0.60    --  111.50 -97.00  10.51   94
 51  ω     72.00 103.00   0.50    0.60    --  111.50 -95.00-150.00   62
 52  ω     48.00  77.00   0.50    0.60    --  111.50-125.00  90.00   58
 53  ω    102.00 135.00   0.50    0.60    --  111.50  30.00  60.00   66
 54  ω    108.00 138.00   0.50    0.60    --  111.50  15.00-180.00   60
 55  ω     41.00  67.00   0.50    0.60    --  111.50 -77.00-150.00   52
 56  ω     69.00 104.00   0.50    0.60    --  111.50 -96.00 -71.93   70
 57  ω     79.00 106.00   0.50    0.60    --  111.50 -97.00 -29.75   54
 58  ω     41.00  81.00   0.50    0.60    --  111.50-125.00-150.00   80
 59  ω     42.00  83.00   0.50    0.60    --  111.50 -95.00  90.00   82
 60  ω     77.00 110.00   0.50    0.60    --  111.50-125.00  60.00   66
 61  ω     52.00 103.00   0.50    0.60    --  111.50-112.00 -78.71  102
 62  ω     66.00 105.00   0.50    0.60    --  111.50 -95.00 -90.00   78
 63  ω    105.00 178.00   0.50    0.60    --  111.50 125.00-120.00  146
 64  ω     96.00 127.00   0.50    0.60    --  111.50 125.00  90.00   62
 65  ω    131.00 160.00   0.50    0.60    --  111.50 125.00  90.00   58
 66  ω     76.00 107.00   0.50    0.60    --  111.50-106.00-100.79   62
 67  ω    111.00 177.00   0.50    0.60    --  111.50  45.00 150.00  132
 68  ω     41.00  66.00   0.50    0.60    --  111.50-125.00  60.00   50
 69  ω     96.00 125.00   0.50    0.60    --  111.50 125.00  60.00   58
 70  ω     45.00  74.00   0.50    0.60    --  111.50-111.00  18.81   58
 71  ω     83.00 108.00   0.50    0.60    --  111.50-111.00  18.81   50
 72  ω    133.00 159.00   0.50    0.60    --  111.50  30.00 -90.00   52
 73  ω     67.00 103.00   0.50    0.60    --  111.50 -77.00 -30.00   72
 74  ω     72.00  98.00   0.50    0.60    --  111.50 -95.00 150.00   52
 75  ω     49.00 107.00   0.50    0.60    --  111.50-106.00  67.84  116
 76  ω    129.00 155.00   0.50    0.60    --  111.50  61.00 120.00   52
 77  ω     41.00  71.00   0.50    0.60    --  111.50 -61.00   0.00   60
 78  ω     99.00 178.00   0.50    0.60    --  111.50  61.00 -90.00  158
 79  ω     41.00 108.00   0.50    0.60    --  111.50-109.00-172.50  134
 80  ω    134.00 160.00   0.50    0.60    --  111.50 125.00  60.00   52
 81  ω    109.00 135.00   0.50    0.60    --  111.50  77.00-150.00   52
 82  ω     48.00  83.00   0.50    0.60    --  111.50 -95.00 -60.00   70
 83  ω    138.00 169.00   0.50    0.60    --  111.50   0.00  60.00   62
 84  ω     50.00  76.00   0.50    0.60    --  111.50 -77.00-180.00   52
 85  ω     42.00  69.00   0.50    0.60    --  111.50 -77.00-120.00   54
 86  ω     44.00  70.00   0.50    0.60    --  111.50 -77.00  30.00   52
 87  ω     60.00  85.00   0.50    0.60    --  111.50 -77.00 120.00   50
 88  ω     51.00  77.00   0.50    0.60    --  111.50 -95.00-180.00   52
 89  ω     50.00  76.00   0.50    0.60    --  111.50 -95.00-120.00   52
 90  ω     46.00  72.00   0.50    0.60    --  111.50-111.00 -14.89   52
 91  ω     79.00 108.00   0.50    0.60    --  111.50-111.00 -14.89   58
 92  ω     75.00 101.00   0.50    0.60    --  111.50-125.00-180.00   52
 93  ω     58.00 110.00   0.50    0.60    --  111.50-125.00  30.00  104
 94  ω     67.00  93.00   0.50    0.60    --  111.50-125.00 120.00   52
 95  ω    102.00 172.00   0.50    0.60    --  111.50  30.00 -30.00  140
 96  ω     40.00  68.00   0.50    0.60    --  111.50 -61.00-150.00   56
 97  ω    104.00 137.00   0.50    0.60    --  111.50  15.00-150.00   66
 98  ω    103.00 146.00   0.50    0.60    --  111.50  61.00 -30.00   86
 99  ω     97.00 169.00   0.50    0.60    --  111.50  61.00  90.00  144
100  ω    117.00 143.00   0.50    0.60    --  111.50 124.00 147.77   52
101  ω    142.00 167.00   0.50    0.60    --  111.50 125.00 150.00   50
102  ω     84.00 110.00   0.50    0.60    --  111.50-162.00 -17.59   52
103  ω     86.00 112.00   0.50    0.60    --  111.50 -85.00-140.77   52
104  ω     87.00 113.00   0.50    0.60    --  111.50 -86.00  69.67   52
105  ω     47.00  73.00   0.50    0.60    --  111.50 -88.00-167.96   52
106  ω     42.00  85.00   0.50    0.60    --  111.50 -88.00 105.10   86
107  ω    110.00 136.00   0.50    0.60    --  111.50 -88.00 105.10   52
108  ω     99.00 171.00   0.50    0.60    --  111.50  53.00   1.33  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594560000
_diffrn_orient_matrix_UB_12      0.0637336000
_diffrn_orient_matrix_UB_13      0.0109876000
_diffrn_orient_matrix_UB_21      -0.0347072000
_diffrn_orient_matrix_UB_22      0.1096387000
_diffrn_orient_matrix_UB_23      -0.0016310000
_diffrn_orient_matrix_UB_31      -0.0026066000
_diffrn_orient_matrix_UB_32      -0.0047205000
_diffrn_orient_matrix_UB_33      0.1133756000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7522
_reflns_number_total             7887
_reflns_odcompleteness_completeness 94.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         7887
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.187
_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)+(0.0989P)²+8.7132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2347
_refine_ls_wR_factor_ref         0.2380
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9763(7)
 0.0237(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C15B(H15C,H15D), C16B(H16C,H16D), C17B(H17C,H17D),
 C18B(H18C,H18D), C19B(H19C,H19D), C20B(H20C,H20D)
3.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C11A(H11A), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B), C11B(H11B)
3.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C)
;
_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
O1A O 0.51596(10) 0.71242(18) 0.15354(16) 0.0209(4) Uani 1 1 d . . . . .
H1A H 0.5235(19) 0.741(4) 0.099(4) 0.031 Uiso 1 1 d . U . . .
O2A O 0.40535(10) 0.71039(18) 0.20098(16) 0.0220(5) Uani 1 1 d . . . . .
H2A H 0.429(2) 0.672(4) 0.168(3) 0.033 Uiso 1 1 d . U . . .
O3A O 0.57547(10) 0.9445(2) 0.19084(18) 0.0280(5) Uani 1 1 d . . . . .
N1A N 0.53392(11) 0.7630(2) 0.31573(17) 0.0169(5) Uani 1 1 d . . . . .
N2A N 0.54317(11) 0.7199(2) 0.47602(18) 0.0180(5) Uani 1 1 d . . . . .
C1A C 0.50581(13) 0.7468(2) 0.4017(2) 0.0173(5) Uani 1 1 d . . . . .
C2A C 0.59972(13) 0.7157(2) 0.4366(2) 0.0184(6) Uani 1 1 d . . . . .
C3A C 0.65517(14) 0.6888(3) 0.4822(2) 0.0234(6) Uani 1 1 d . . . . .
H3A H 0.659026 0.671373 0.550585 0.028 Uiso 1 1 calc R U . . .
C4A C 0.70429(14) 0.6882(3) 0.4245(3) 0.0260(7) Uani 1 1 d . . . . .
H4A H 0.742655 0.671351 0.453889 0.031 Uiso 1 1 calc R U . . .
C5A C 0.69834(15) 0.7122(3) 0.3230(3) 0.0279(7) Uani 1 1 d . . . . .
H5A H 0.732893 0.709950 0.285197 0.034 Uiso 1 1 calc R U . . .
C6A C 0.64390(14) 0.7389(3) 0.2763(2) 0.0250(6) Uani 1 1 d . . . . .
H6A H 0.640066 0.754508 0.207506 0.030 Uiso 1 1 calc R U . . .
C7A C 0.59473(13) 0.7417(2) 0.3358(2) 0.0190(6) Uani 1 1 d . . . . .
C8A C 0.50450(13) 0.7954(2) 0.2223(2) 0.0173(6) Uani 1 1 d . . . . .
C9A C 0.43486(13) 0.8101(2) 0.2274(2) 0.0180(6) Uani 1 1 d . . . . .
C10A C 0.42304(14) 0.8979(2) 0.1477(2) 0.0205(6) Uani 1 1 d . . . . .
C11A C 0.47288(14) 0.9533(3) 0.1275(2) 0.0218(6) Uani 1 1 d . . . . .
H11A H 0.473949 1.013985 0.083296 0.026 Uiso 1 1 calc R U . . .
C12A C 0.52491(14) 0.9083(2) 0.1819(2) 0.0201(6) Uani 1 1 d . . . . .
C13A C 0.36269(15) 0.9142(3) 0.0979(2) 0.0285(7) Uani 1 1 d . . . . .
H13A H 0.367036 0.938325 0.029681 0.043 Uiso 1 1 calc R U . . .
H13B H 0.340848 0.970282 0.133532 0.043 Uiso 1 1 calc R U . . .
H13C H 0.340505 0.844549 0.097927 0.043 Uiso 1 1 calc R U . . .
C14A C 0.41489(13) 0.8445(2) 0.3324(2) 0.0172(6) Uani 1 1 d . . . . .
C15A C 0.43976(13) 0.7549(2) 0.4033(2) 0.0180(6) Uani 1 1 d . . . . .
H15A H 0.428483 0.772066 0.471321 0.022 Uiso 1 1 calc R U . . .
H15B H 0.421719 0.683025 0.384208 0.022 Uiso 1 1 calc R U . . .
C16A C 0.34600(13) 0.8464(3) 0.3346(2) 0.0220(6) Uani 1 1 d . . . . .
H16A H 0.329654 0.895898 0.281750 0.026 Uiso 1 1 calc R U . . .
H16B H 0.330344 0.771432 0.320701 0.026 Uiso 1 1 calc R U . . .
C17A C 0.32413(14) 0.8856(3) 0.4345(2) 0.0263(7) Uani 1 1 d . . . . .
H17A H 0.279908 0.890003 0.430381 0.032 Uiso 1 1 calc R U . . .
H17B H 0.336141 0.831358 0.486326 0.032 Uiso 1 1 calc R U . . .
C18A C 0.34996(15) 0.9981(3) 0.4629(3) 0.0280(7) Uani 1 1 d . . . . .
H18A H 0.337509 1.018485 0.529543 0.034 Uiso 1 1 calc R U . . .
H18B H 0.333990 1.054246 0.415541 0.034 Uiso 1 1 calc R U . . .
C19A C 0.41840(14) 0.9968(3) 0.4628(2) 0.0236(6) Uani 1 1 d . . . . .
H19A H 0.434548 0.946419 0.515109 0.028 Uiso 1 1 calc R U . . .
H19B H 0.434017 1.071647 0.477641 0.028 Uiso 1 1 calc R U . . .
C20A C 0.43943(13) 0.9590(2) 0.3624(2) 0.0187(6) Uani 1 1 d . . . . .
H20A H 0.483689 0.956777 0.365196 0.022 Uiso 1 1 calc R U . . .
H20B H 0.426234 1.013360 0.311247 0.022 Uiso 1 1 calc R U . . .
O1B O 0.00931(10) 0.71214(18) 0.83067(16) 0.0232(5) Uani 1 1 d . . . . .
H1B H 0.009(2) 0.744(4) 0.891(4) 0.035 Uiso 1 1 d . U . . .
O2B O -0.10238(10) 0.71264(18) 0.76435(17) 0.0230(5) Uani 1 1 d . . . . .
H2B H -0.077(2) 0.668(4) 0.793(3) 0.034 Uiso 1 1 d . U . . .
O3B O 0.06915(11) 0.9464(2) 0.7985(2) 0.0320(6) Uani 1 1 d . . . . .
N1B N 0.02713(11) 0.7622(2) 0.67132(18) 0.0184(5) Uani 1 1 d . . . . .
N2B N 0.03529(11) 0.7167(2) 0.51265(18) 0.0201(5) Uani 1 1 d . . . . .
C1B C -0.00146(13) 0.7451(2) 0.5807(2) 0.0185(6) Uani 1 1 d . . . . .
C2B C 0.09209(14) 0.7129(3) 0.5614(2) 0.0208(6) Uani 1 1 d . . . . .
C3B C 0.14751(14) 0.6874(3) 0.5238(2) 0.0252(6) Uani 1 1 d . . . . .
H3B H 0.150861 0.669261 0.456108 0.030 Uiso 1 1 calc R U . . .
C4B C 0.19713(15) 0.6897(3) 0.5888(3) 0.0284(7) Uani 1 1 d . . . . .
H4B H 0.235371 0.673682 0.565195 0.034 Uiso 1 1 calc R U . . .
C5B C 0.19227(15) 0.7152(3) 0.6889(3) 0.0295(7) Uani 1 1 d . . . . .
H5B H 0.227298 0.714920 0.731637 0.035 Uiso 1 1 calc R U . . .
C6B C 0.13766(14) 0.7408(3) 0.7275(3) 0.0263(7) Uani 1 1 d . . . . .
H6B H 0.134354 0.757829 0.795402 0.032 Uiso 1 1 calc R U . . .
C7B C 0.08796(13) 0.7402(2) 0.6608(2) 0.0199(6) Uani 1 1 d . . . . .
C8B C -0.00196(14) 0.7950(2) 0.7600(2) 0.0192(6) Uani 1 1 d . . . . .
C9B C -0.07168(13) 0.8116(2) 0.7431(2) 0.0195(6) Uani 1 1 d . . . . .
C10B C -0.08243(14) 0.8990(3) 0.8214(2) 0.0227(6) Uani 1 1 d . . . . .
C11B C -0.03216(15) 0.9533(3) 0.8507(2) 0.0239(6) Uani 1 1 d . . . . .
H11B H -0.030467 1.012824 0.896234 0.029 Uiso 1 1 calc R U . . .
C12B C 0.01926(14) 0.9083(3) 0.8030(2) 0.0232(6) Uani 1 1 d . . . . .
C13B C -0.14282(15) 0.9178(3) 0.8611(3) 0.0301(7) Uani 1 1 d . . . . .
H13D H -0.138050 0.945037 0.929111 0.045 Uiso 1 1 calc R U . . .
H13E H -0.165131 0.848294 0.860082 0.045 Uiso 1 1 calc R U . . .
H13F H -0.164766 0.972294 0.819955 0.045 Uiso 1 1 calc R U . . .
C14B C -0.09107(13) 0.8474(2) 0.6350(2) 0.0190(6) Uani 1 1 d . . . . .
C15B C -0.06737(13) 0.7561(3) 0.5680(2) 0.0204(6) Uani 1 1 d . . . . .
H15C H -0.086290 0.685084 0.584135 0.024 Uiso 1 1 calc R U . . .
H15D H -0.078572 0.773654 0.498118 0.024 Uiso 1 1 calc R U . . .
C16B C -0.06496(13) 0.9606(3) 0.6102(2) 0.0214(6) Uani 1 1 d . . . . .
H16C H -0.078187 1.015619 0.658386 0.026 Uiso 1 1 calc R U . . .
H16D H -0.020757 0.956728 0.616611 0.026 Uiso 1 1 calc R U . . .
C17B C -0.08420(14) 0.9989(3) 0.5056(2) 0.0253(6) Uani 1 1 d . . . . .
H17C H -0.067184 1.072670 0.493738 0.030 Uiso 1 1 calc R U . . .
H17D H -0.068329 0.947231 0.456842 0.030 Uiso 1 1 calc R U . . .
C18B C -0.15234(15) 1.0040(3) 0.4914(3) 0.0309(7) Uani 1 1 d . . . . .
H18C H -0.163691 1.024363 0.422231 0.037 Uiso 1 1 calc R U . . .
H18D H -0.167898 1.061388 0.535187 0.037 Uiso 1 1 calc R U . . .
C19B C -0.18027(14) 0.8927(3) 0.5153(3) 0.0275(7) Uani 1 1 d . . . . .
H19C H -0.168663 0.837446 0.466170 0.033 Uiso 1 1 calc R U . . .
H19D H -0.224401 0.899482 0.510575 0.033 Uiso 1 1 calc R U . . .
C20B C -0.15998(13) 0.8531(3) 0.6196(2) 0.0230(6) Uani 1 1 d . . . . .
H20C H -0.176996 0.779178 0.630891 0.028 Uiso 1 1 calc R U . . .
H20D H -0.175831 0.903981 0.669055 0.028 Uiso 1 1 calc R U . . .
O4 O 0.26752(18) 0.6127(3) 0.3815(2) 0.0646(11) Uani 1 1 d . . . . .
C21 C 0.25720(15) 0.5420(3) 0.3204(3) 0.0278(7) Uani 1 1 d . . . . .
C22 C 0.21274(19) 0.4538(4) 0.3385(4) 0.0445(10) Uani 1 1 d . . . . .
H22A H 0.231513 0.381514 0.331387 0.067 Uiso 1 1 calc R U . . .
H22B H 0.178653 0.460657 0.290472 0.067 Uiso 1 1 calc R U . . .
H22C H 0.198839 0.461342 0.405553 0.067 Uiso 1 1 calc R U . . .
C23 C 0.28764(16) 0.5381(3) 0.2246(3) 0.0318(7) Uani 1 1 d . . . . .
H23A H 0.257622 0.543202 0.169512 0.048 Uiso 1 1 calc R U . . .
H23B H 0.309610 0.468614 0.220185 0.048 Uiso 1 1 calc R U . . .
H23C H 0.315596 0.600007 0.221596 0.048 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
O1A H1A 0.84(5) . ?
O1A C8A 1.405(3) . ?
O2A H2A 0.85(5) . ?
O2A C9A 1.416(3) . ?
O3A C12A 1.214(4) . ?
N1A C1A 1.367(4) . ?
N1A C7A 1.398(4) . ?
N1A C8A 1.451(3) . ?
N2A C1A 1.316(4) . ?
N2A C2A 1.401(4) . ?
C1A C15A 1.483(4) . ?
C2A C3A 1.396(4) . ?
C2A C7A 1.400(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.383(5) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.405(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.382(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.399(4) . ?
C8A C9A 1.574(4) . ?
C8A C12A 1.553(4) . ?
C9A C10A 1.530(4) . ?
C9A C14A 1.571(4) . ?
C10A C11A 1.343(4) . ?
C10A C13A 1.491(4) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.452(4) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A C15A 1.536(4) . ?
C14A C16A 1.544(4) . ?
C14A C20A 1.541(4) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C17A 1.538(4) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17A C18A 1.524(5) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A C19A 1.532(4) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C19A C20A 1.533(4) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
O1B H1B 0.91(5) . ?
O1B C8B 1.402(4) . ?
O2B H2B 0.86(5) . ?
O2B C9B 1.421(4) . ?
O3B C12B 1.213(4) . ?
N1B C1B 1.370(4) . ?
N1B C7B 1.402(4) . ?
N1B C8B 1.452(4) . ?
N2B C1B 1.314(4) . ?
N2B C2B 1.402(4) . ?
C1B C15B 1.482(4) . ?
C2B C3B 1.400(4) . ?
C2B C7B 1.395(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.381(5) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.400(5) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.390(5) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.396(4) . ?
C8B C9B 1.579(4) . ?
C8B C12B 1.559(4) . ?
C9B C10B 1.528(4) . ?
C9B C14B 1.567(4) . ?
C10B C11B 1.345(5) . ?
C10B C13B 1.498(4) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.455(4) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B C15B 1.544(4) . ?
C14B C16B 1.538(4) . ?
C14B C20B 1.547(4) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C16B C17B 1.531(4) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.529(4) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.530(5) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C19B C20B 1.538(5) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
O4 C21 1.206(5) . ?
C21 C22 1.490(5) . ?
C21 C23 1.498(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C8A O1A H1A 109(3) . . ?
C9A O2A H2A 107(3) . . ?
C1A N1A C7A 107.1(2) . . ?
C1A N1A C8A 125.1(2) . . ?
C7A N1A C8A 127.8(2) . . ?
C1A N2A C2A 105.6(2) . . ?
N1A C1A C15A 120.5(2) . . ?
N2A C1A N1A 112.6(3) . . ?
N2A C1A C15A 126.8(3) . . ?
C3A C2A N2A 129.8(3) . . ?
C3A C2A C7A 120.5(3) . . ?
C7A C2A N2A 109.7(3) . . ?
C2A C3A H3A 121.1 . . ?
C4A C3A C2A 117.8(3) . . ?
C4A C3A H3A 121.1 . . ?
C3A C4A H4A 119.5 . . ?
C3A C4A C5A 121.0(3) . . ?
C5A C4A H4A 119.5 . . ?
C4A C5A H5A 118.9 . . ?
C6A C5A C4A 122.2(3) . . ?
C6A C5A H5A 118.9 . . ?
C5A C6A H6A 121.8 . . ?
C5A C6A C7A 116.3(3) . . ?
C7A C6A H6A 121.8 . . ?
N1A C7A C2A 105.0(2) . . ?
N1A C7A C6A 132.8(3) . . ?
C6A C7A C2A 122.2(3) . . ?
O1A C8A N1A 107.1(2) . . ?
O1A C8A C9A 109.1(2) . . ?
O1A C8A C12A 109.4(2) . . ?
N1A C8A C9A 113.4(2) . . ?
N1A C8A C12A 114.7(2) . . ?
C12A C8A C9A 103.0(2) . . ?
O2A C9A C8A 110.0(2) . . ?
O2A C9A C10A 110.9(2) . . ?
O2A C9A C14A 107.7(2) . . ?
C10A C9A C8A 100.5(2) . . ?
C10A C9A C14A 114.1(2) . . ?
C14A C9A C8A 113.6(2) . . ?
C11A C10A C9A 112.2(3) . . ?
C11A C10A C13A 125.8(3) . . ?
C13A C10A C9A 122.0(3) . . ?
C10A C11A H11A 124.4 . . ?
C10A C11A C12A 111.2(3) . . ?
C12A C11A H11A 124.4 . . ?
O3A C12A C8A 125.1(3) . . ?
O3A C12A C11A 129.3(3) . . ?
C11A C12A C8A 105.5(2) . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15A C14A C9A 105.5(2) . . ?
C15A C14A C16A 109.1(2) . . ?
C15A C14A C20A 111.2(2) . . ?
C16A C14A C9A 110.7(2) . . ?
C20A C14A C9A 111.3(2) . . ?
C20A C14A C16A 108.9(2) . . ?
C1A C15A C14A 111.5(2) . . ?
C1A C15A H15A 109.3 . . ?
C1A C15A H15B 109.3 . . ?
C14A C15A H15A 109.3 . . ?
C14A C15A H15B 109.3 . . ?
H15A C15A H15B 108.0 . . ?
C14A C16A H16A 109.0 . . ?
C14A C16A H16B 109.0 . . ?
H16A C16A H16B 107.8 . . ?
C17A C16A C14A 112.7(2) . . ?
C17A C16A H16A 109.0 . . ?
C17A C16A H16B 109.0 . . ?
C16A C17A H17A 109.3 . . ?
C16A C17A H17B 109.3 . . ?
H17A C17A H17B 108.0 . . ?
C18A C17A C16A 111.4(3) . . ?
C18A C17A H17A 109.3 . . ?
C18A C17A H17B 109.3 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A C19A 110.9(3) . . ?
H18A C18A H18B 108.0 . . ?
C19A C18A H18A 109.5 . . ?
C19A C18A H18B 109.5 . . ?
C18A C19A H19A 109.4 . . ?
C18A C19A H19B 109.4 . . ?
C18A C19A C20A 111.0(3) . . ?
H19A C19A H19B 108.0 . . ?
C20A C19A H19A 109.4 . . ?
C20A C19A H19B 109.4 . . ?
C14A C20A H20A 109.1 . . ?
C14A C20A H20B 109.1 . . ?
C19A C20A C14A 112.4(2) . . ?
C19A C20A H20A 109.1 . . ?
C19A C20A H20B 109.1 . . ?
H20A C20A H20B 107.9 . . ?
C8B O1B H1B 107(3) . . ?
C9B O2B H2B 108(3) . . ?
C1B N1B C7B 106.9(2) . . ?
C1B N1B C8B 125.0(2) . . ?
C7B N1B C8B 128.1(2) . . ?
C1B N2B C2B 105.3(2) . . ?
N1B C1B C15B 120.4(3) . . ?
N2B C1B N1B 112.9(3) . . ?
N2B C1B C15B 126.7(3) . . ?
C3B C2B N2B 129.4(3) . . ?
C7B C2B N2B 110.0(3) . . ?
C7B C2B C3B 120.6(3) . . ?
C2B C3B H3B 121.3 . . ?
C4B C3B C2B 117.5(3) . . ?
C4B C3B H3B 121.3 . . ?
C3B C4B H4B 119.3 . . ?
C3B C4B C5B 121.4(3) . . ?
C5B C4B H4B 119.3 . . ?
C4B C5B H5B 119.1 . . ?
C6B C5B C4B 121.9(3) . . ?
C6B C5B H5B 119.1 . . ?
C5B C6B H6B 121.9 . . ?
C5B C6B C7B 116.3(3) . . ?
C7B C6B H6B 121.9 . . ?
C2B C7B N1B 104.9(3) . . ?
C2B C7B C6B 122.3(3) . . ?
C6B C7B N1B 132.7(3) . . ?
O1B C8B N1B 107.3(2) . . ?
O1B C8B C9B 109.4(2) . . ?
O1B C8B C12B 109.7(2) . . ?
N1B C8B C9B 113.5(2) . . ?
N1B C8B C12B 114.2(2) . . ?
C12B C8B C9B 102.8(2) . . ?
O2B C9B C8B 110.3(2) . . ?
O2B C9B C10B 110.5(2) . . ?
O2B C9B C14B 108.1(2) . . ?
C10B C9B C8B 100.3(2) . . ?
C10B C9B C14B 114.2(2) . . ?
C14B C9B C8B 113.2(2) . . ?
C11B C10B C9B 112.6(3) . . ?
C11B C10B C13B 125.2(3) . . ?
C13B C10B C9B 122.2(3) . . ?
C10B C11B H11B 124.6 . . ?
C10B C11B C12B 110.8(3) . . ?
C12B C11B H11B 124.6 . . ?
O3B C12B C8B 125.5(3) . . ?
O3B C12B C11B 129.1(3) . . ?
C11B C12B C8B 105.3(3) . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C15B C14B C9B 105.3(2) . . ?
C15B C14B C20B 108.9(2) . . ?
C16B C14B C9B 111.3(2) . . ?
C16B C14B C15B 111.5(2) . . ?
C16B C14B C20B 108.5(2) . . ?
C20B C14B C9B 111.3(2) . . ?
C1B C15B C14B 111.5(2) . . ?
C1B C15B H15C 109.3 . . ?
C1B C15B H15D 109.3 . . ?
C14B C15B H15C 109.3 . . ?
C14B C15B H15D 109.3 . . ?
H15C C15B H15D 108.0 . . ?
C14B C16B H16C 109.1 . . ?
C14B C16B H16D 109.1 . . ?
H16C C16B H16D 107.8 . . ?
C17B C16B C14B 112.5(3) . . ?
C17B C16B H16C 109.1 . . ?
C17B C16B H16D 109.1 . . ?
C16B C17B H17C 109.4 . . ?
C16B C17B H17D 109.4 . . ?
H17C C17B H17D 108.0 . . ?
C18B C17B C16B 111.0(3) . . ?
C18B C17B H17C 109.4 . . ?
C18B C17B H17D 109.4 . . ?
C17B C18B H18C 109.5 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B C19B 110.7(3) . . ?
H18C C18B H18D 108.1 . . ?
C19B C18B H18C 109.5 . . ?
C19B C18B H18D 109.5 . . ?
C18B C19B H19C 109.3 . . ?
C18B C19B H19D 109.3 . . ?
C18B C19B C20B 111.5(3) . . ?
H19C C19B H19D 108.0 . . ?
C20B C19B H19C 109.3 . . ?
C20B C19B H19D 109.3 . . ?
C14B C20B H20C 109.1 . . ?
C14B C20B H20D 109.1 . . ?
C19B C20B C14B 112.4(3) . . ?
C19B C20B H20C 109.1 . . ?
C19B C20B H20D 109.1 . . ?
H20C C20B H20D 107.8 . . ?
O4 C21 C22 120.2(4) . . ?
O4 C21 C23 122.5(3) . . ?
C22 C21 C23 117.3(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O1A H1A N2A 0.84(5) 1.81(5) 2.643(3) 170(4) 4_575 yes
O2A H2A O1A 0.85(5) 2.02(4) 2.591(3) 124(4) . yes
O1B H1B N2B 0.91(5) 1.79(5) 2.648(3) 158(4) 4_576 yes
O2B H2B O1B 0.86(5) 2.05(4) 2.612(3) 122(4) . 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
O1A C8A C9A O2A 26.8(3) . . . . ?
O1A C8A C9A C10A -90.2(3) . . . . ?
O1A C8A C9A C14A 147.6(2) . . . . ?
O1A C8A C12A O3A -85.0(4) . . . . ?
O1A C8A C12A C11A 90.8(3) . . . . ?
O2A C9A C10A C11A -136.1(3) . . . . ?
O2A C9A C10A C13A 41.9(4) . . . . ?
O2A C9A C14A C15A 65.5(3) . . . . ?
O2A C9A C14A C16A -52.4(3) . . . . ?
O2A C9A C14A C20A -173.7(2) . . . . ?
N1A C1A C15A C14A -35.5(4) . . . . ?
N1A C8A C9A O2A -92.5(3) . . . . ?
N1A C8A C9A C10A 150.6(2) . . . . ?
N1A C8A C9A C14A 28.4(3) . . . . ?
N1A C8A C12A O3A 35.4(4) . . . . ?
N1A C8A C12A C11A -148.8(2) . . . . ?
N2A C1A C15A C14A 147.7(3) . . . . ?
N2A C2A C3A C4A 178.2(3) . . . . ?
N2A C2A C7A N1A 0.7(3) . . . . ?
N2A C2A C7A C6A -176.9(3) . . . . ?
C1A N1A C7A C2A -1.4(3) . . . . ?
C1A N1A C7A C6A 175.9(3) . . . . ?
C1A N1A C8A O1A -120.9(3) . . . . ?
C1A N1A C8A C9A -0.5(4) . . . . ?
C1A N1A C8A C12A 117.5(3) . . . . ?
C1A N2A C2A C3A -178.4(3) . . . . ?
C1A N2A C2A C7A 0.3(3) . . . . ?
C2A N2A C1A N1A -1.2(3) . . . . ?
C2A N2A C1A C15A 175.8(3) . . . . ?
C2A C3A C4A C5A -1.0(5) . . . . ?
C3A C2A C7A N1A 179.5(3) . . . . ?
C3A C2A C7A C6A 1.9(5) . . . . ?
C3A C4A C5A C6A 1.0(5) . . . . ?
C4A C5A C6A C7A 0.5(5) . . . . ?
C5A C6A C7A N1A -178.8(3) . . . . ?
C5A C6A C7A C2A -1.9(5) . . . . ?
C7A N1A C1A N2A 1.7(3) . . . . ?
C7A N1A C1A C15A -175.5(3) . . . . ?
C7A N1A C8A O1A 58.6(4) . . . . ?
C7A N1A C8A C9A 179.0(3) . . . . ?
C7A N1A C8A C12A -63.0(4) . . . . ?
C7A C2A C3A C4A -0.3(5) . . . . ?
C8A N1A C1A N2A -178.7(3) . . . . ?
C8A N1A C1A C15A 4.1(4) . . . . ?
C8A N1A C7A C2A 179.1(3) . . . . ?
C8A N1A C7A C6A -3.7(5) . . . . ?
C8A C9A C10A C11A -19.8(3) . . . . ?
C8A C9A C10A C13A 158.2(3) . . . . ?
C8A C9A C14A C15A -56.6(3) . . . . ?
C8A C9A C14A C16A -174.5(2) . . . . ?
C8A C9A C14A C20A 64.2(3) . . . . ?
C9A C8A C12A O3A 159.1(3) . . . . ?
C9A C8A C12A C11A -25.1(3) . . . . ?
C9A C10A C11A C12A 4.3(4) . . . . ?
C9A C14A C15A C1A 59.1(3) . . . . ?
C9A C14A C16A C17A -177.0(2) . . . . ?
C9A C14A C20A C19A 177.6(2) . . . . ?
C10A C9A C14A C15A -170.9(2) . . . . ?
C10A C9A C14A C16A 71.1(3) . . . . ?
C10A C9A C14A C20A -50.2(3) . . . . ?
C10A C11A C12A O3A -170.7(3) . . . . ?
C10A C11A C12A C8A 13.7(3) . . . . ?
C12A C8A C9A O2A 142.9(2) . . . . ?
C12A C8A C9A C10A 26.0(3) . . . . ?
C12A C8A C9A C14A -96.2(3) . . . . ?
C13A C10A C11A C12A -173.6(3) . . . . ?
C14A C9A C10A C11A 102.1(3) . . . . ?
C14A C9A C10A C13A -79.9(3) . . . . ?
C14A C16A C17A C18A 55.3(3) . . . . ?
C15A C14A C16A C17A 67.3(3) . . . . ?
C15A C14A C20A C19A -65.1(3) . . . . ?
C16A C14A C15A C1A 178.1(2) . . . . ?
C16A C14A C20A C19A 55.2(3) . . . . ?
C16A C17A C18A C19A -55.0(4) . . . . ?
C17A C18A C19A C20A 55.8(4) . . . . ?
C18A C19A C20A C14A -57.0(3) . . . . ?
C20A C14A C15A C1A -61.7(3) . . . . ?
C20A C14A C16A C17A -54.2(3) . . . . ?
O1B C8B C9B O2B -27.0(3) . . . . ?
O1B C8B C9B C10B 89.6(3) . . . . ?
O1B C8B C9B C14B -148.3(2) . . . . ?
O1B C8B C12B O3B 88.4(4) . . . . ?
O1B C8B C12B C11B -89.7(3) . . . . ?
O2B C9B C10B C11B 136.3(3) . . . . ?
O2B C9B C10B C13B -42.3(4) . . . . ?
O2B C9B C14B C15B -65.2(3) . . . . ?
O2B C9B C14B C16B 173.9(2) . . . . ?
O2B C9B C14B C20B 52.7(3) . . . . ?
N1B C1B C15B C14B 34.4(4) . . . . ?
N1B C8B C9B O2B 92.7(3) . . . . ?
N1B C8B C9B C10B -150.7(2) . . . . ?
N1B C8B C9B C14B -28.6(3) . . . . ?
N1B C8B C12B O3B -32.0(4) . . . . ?
N1B C8B C12B C11B 149.9(3) . . . . ?
N2B C1B C15B C14B -147.6(3) . . . . ?
N2B C2B C3B C4B -179.9(3) . . . . ?
N2B C2B C7B N1B -0.7(3) . . . . ?
N2B C2B C7B C6B 178.7(3) . . . . ?
C1B N1B C7B C2B 1.2(3) . . . . ?
C1B N1B C7B C6B -178.0(3) . . . . ?
C1B N1B C8B O1B 120.1(3) . . . . ?
C1B N1B C8B C9B -0.8(4) . . . . ?
C1B N1B C8B C12B -118.1(3) . . . . ?
C1B N2B C2B C3B -179.7(3) . . . . ?
C1B N2B C2B C7B -0.1(3) . . . . ?
C2B N2B C1B N1B 0.9(3) . . . . ?
C2B N2B C1B C15B -177.3(3) . . . . ?
C2B C3B C4B C5B 0.8(5) . . . . ?
C3B C2B C7B N1B 178.9(3) . . . . ?
C3B C2B C7B C6B -1.7(5) . . . . ?
C3B C4B C5B C6B -0.9(5) . . . . ?
C4B C5B C6B C7B -0.2(5) . . . . ?
C5B C6B C7B N1B -179.3(3) . . . . ?
C5B C6B C7B C2B 1.5(5) . . . . ?
C7B N1B C1B N2B -1.4(4) . . . . ?
C7B N1B C1B C15B 176.9(3) . . . . ?
C7B N1B C8B O1B -58.7(4) . . . . ?
C7B N1B C8B C9B -179.6(3) . . . . ?
C7B N1B C8B C12B 63.1(4) . . . . ?
C7B C2B C3B C4B 0.5(5) . . . . ?
C8B N1B C1B N2B 179.6(3) . . . . ?
C8B N1B C1B C15B -2.1(4) . . . . ?
C8B N1B C7B C2B -179.8(3) . . . . ?
C8B N1B C7B C6B 0.9(6) . . . . ?
C8B C9B C10B C11B 19.8(3) . . . . ?
C8B C9B C10B C13B -158.7(3) . . . . ?
C8B C9B C14B C15B 57.3(3) . . . . ?
C8B C9B C14B C16B -63.6(3) . . . . ?
C8B C9B C14B C20B 175.2(2) . . . . ?
C9B C8B C12B O3B -155.3(3) . . . . ?
C9B C8B C12B C11B 26.6(3) . . . . ?
C9B C10B C11B C12B -3.3(4) . . . . ?
C9B C14B C15B C1B -59.5(3) . . . . ?
C9B C14B C16B C17B -178.9(2) . . . . ?
C9B C14B C20B C19B 177.6(3) . . . . ?
C10B C9B C14B C15B 171.3(2) . . . . ?
C10B C9B C14B C16B 50.4(3) . . . . ?
C10B C9B C14B C20B -70.8(3) . . . . ?
C10B C11B C12B O3B 166.7(3) . . . . ?
C10B C11B C12B C8B -15.3(4) . . . . ?
C12B C8B C9B O2B -143.5(2) . . . . ?
C12B C8B C9B C10B -26.9(3) . . . . ?
C12B C8B C9B C14B 95.3(3) . . . . ?
C13B C10B C11B C12B 175.2(3) . . . . ?
C14B C9B C10B C11B -101.6(3) . . . . ?
C14B C9B C10B C13B 79.9(4) . . . . ?
C14B C16B C17B C18B 57.7(4) . . . . ?
C15B C14B C16B C17B 63.9(3) . . . . ?
C15B C14B C20B C19B -66.7(3) . . . . ?
C16B C14B C15B C1B 61.3(3) . . . . ?
C16B C14B C20B C19B 54.8(3) . . . . ?
C16B C17B C18B C19B -55.7(4) . . . . ?
C17B C18B C19B C20B 54.8(4) . . . . ?
C18B C19B C20B C14B -55.5(4) . . . . ?
C20B C14B C15B C1B -179.0(2) . . . . ?
C20B C14B C16B C17B -56.0(3) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.559
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9763(7)
2 0.0237(7)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C6BNIMNH2NH2
_database_code_depnum_ccdc_archive 'CCDC 2233463'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 N4 O2, C2 H6 O'
_chemical_formula_sum            'C28 H34 N4 O3'
_chemical_formula_weight         474.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H35 N4 O3'
_chemical_oxdiff_usercomment     C6BNIMNH2NH2
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.48626(8)
_cell_length_b                   24.4487(2)
_cell_length_c                   12.18602(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.1288(8)
_cell_angle_gamma                90
_cell_volume                     2471.89(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21621
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.8460
_cell_measurement_theta_min      4.1290
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0309
-2 -1 0 0.0277
1 1 0 0.0319
1 -1 0 0.0291
-2 1 0 0.0272
0 0 -1 0.1829
0 0 1 0.2543
-1 2 0 0.0306
0 -1 0 0.0212
-1 -1 0 0.0282

_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
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
0.0003 0.9991 -0.0004 -0.0542 -0.0299 -0.0114
-1.9992 -0.9912 0.0009 0.2121 -0.2928 0.1044
0.9997 0.9952 -0.0006 -0.1331 0.1315 -0.0579
0.9991 -1.0031 0.0001 -0.0247 0.1912 -0.0350
-1.9986 1.0071 0.0002 0.1036 -0.3525 0.0815
0.0001 0.0004 -0.9995 0.0464 -0.0412 -0.1134
-0.0001 -0.0004 0.9995 -0.0464 0.0412 0.1134
-1.0000 2.0000 -0.0000 -0.0294 -0.2212 0.0237
-0.0000 -1.0000 -0.0000 0.0543 0.0299 0.0114
-1.0000 -1.0000 -0.0000 0.1335 -0.1314 0.0579

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31875
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.523
_diffrn_reflns_theta_min         3.616
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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    -83.00  -3.80   0.40    2.50    --  -48.76 113.00-105.00  198
  2  ω     26.00  89.20   0.40    2.50    --   48.76-113.00 163.00  158
  3  ω   -161.00 -81.00   0.40   10.00    --  -90.00-113.00 163.00  200
  4  ω    -82.00 -18.00   0.40   10.00    --  -90.00 113.00-105.00  160
  5  ω     40.00 108.00   0.40   10.00    --  111.50-113.00 163.00  170
  6  ω    102.00 178.00   0.40   10.00    --  111.50 113.00-105.00  190
  7  ω   -120.00 -73.20   0.40    2.50    --  -48.76-125.00 -30.00  117
  8  ω   -120.00 -73.20   0.40    2.50    --  -48.76-125.00  60.00  117
  9  ω   -120.00 -73.20   0.40    2.50    --  -48.76-125.00-120.00  117
 10  ω   -120.00 -73.20   0.40    2.50    --  -48.76-125.00 -90.00  117
 11  ω    -26.00  26.00   0.40    2.50    --  -48.76  19.00 150.00  130
 12  ω   -120.00 -73.20   0.40    2.50    --  -48.76-125.00-150.00  117
 13  ω     40.00 106.80   0.40   10.00    --  111.50-102.00  -5.54  167
 14  ω     40.00  71.20   0.40   10.00    --  111.50 -61.00  60.00   78
 15  ω     40.00 105.20   0.40   10.00    --  111.50 -95.00-150.00  163
 16  ω     92.00 126.00   0.40   10.00    --  111.50  77.00-180.00   85
 17  ω    134.00 172.00   0.40   10.00    --  111.50  77.00-180.00   95
 18  ω     48.00  90.00   0.40   10.00    --  111.50 -95.00-180.00  105
 19  ω     41.00  70.20   0.40   10.00    --  111.50 -61.00-120.00   73
 20  ω    102.00 138.00   0.40   10.00    --  111.50  45.00-120.00   90
 21  ω     41.00  70.20   0.40   10.00    --  111.50 -61.00-150.00   73
 22  ω     41.00  67.00   0.40   10.00    --  111.50 -77.00-120.00   65
 23  ω     43.00  69.00   0.40   10.00    --  111.50 -61.00  30.00   65
 24  ω     81.00 107.00   0.40   10.00    --  111.50-109.00  -8.21   65
 25  ω     42.00 108.00   0.40   10.00    --  111.50-119.00 151.62  165
 26  ω     98.00 124.00   0.40   10.00    --  111.50  61.00-150.00   65
 27  ω    141.00 168.20   0.40   10.00    --  111.50  61.00-150.00   68
 28  ω     84.00 109.20   0.40   10.00    --  111.50-125.00 -60.00   63
 29  ω     42.00 106.00   0.40   10.00    --  111.50-113.00-167.03  160
 30  ω     90.00 129.20   0.40   10.00    --  111.50-150.00 -83.69   98
 31  ω    101.00 173.00   0.40   10.00    --  111.50  15.00 -30.00  180
 32  ω    101.00 140.20   0.40   10.00    --  111.50  30.00   0.00   98
 33  ω     72.00 104.00   0.40   10.00    --  111.50 -77.00-180.00   80
 34  ω    104.00 131.20   0.40   10.00    --  111.50  30.00-150.00   68
 35  ω    139.00 165.00   0.40   10.00    --  111.50  30.00-150.00   65
 36  ω     50.00  90.00   0.40   10.00    --  111.50-125.00 150.00  100
 37  ω     49.00  88.20   0.40   10.00    --  111.50-101.00 -64.71   98
 38  ω    145.00 171.00   0.40   10.00    --  111.50  30.00   0.00   65
 39  ω     53.00  79.00   0.40   10.00    --  111.50 -82.00 179.19   65
 40  ω    106.00 132.00   0.40   10.00    --  111.50 -82.00 179.19   65
 41  ω     99.00 129.00   0.40   10.00    --  111.50 -82.00 115.81   75
 42  ω     41.00  68.20   0.40   10.00    --  111.50 -61.00   0.00   68
 43  ω     52.00  78.00   0.40   10.00    --  111.50 -77.00  90.00   65
 44  ω     83.00 109.00   0.40   10.00    --  111.50-125.00 -90.00   65
 45  ω    109.00 177.00   0.40   10.00    --  111.50  30.00  90.00  170
 46  ω    119.00 145.00   0.40   10.00    --  111.50  61.00 -90.00   65
 47  ω     41.00  70.20   0.40   10.00    --  111.50 -61.00 -30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0791822000
_diffrn_orient_matrix_UB_12      -0.0542787000
_diffrn_orient_matrix_UB_13      -0.0464464000
_diffrn_orient_matrix_UB_21      0.1613161000
_diffrn_orient_matrix_UB_22      -0.0299407000
_diffrn_orient_matrix_UB_23      0.0412166000
_diffrn_orient_matrix_UB_31      -0.0465179000
_diffrn_orient_matrix_UB_32      -0.0114026000
_diffrn_orient_matrix_UB_33      0.1134344000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5026
_reflns_number_total             5343
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00118(19)
_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   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.076
_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)+(0.0516P)²+0.9647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.41114(10) 0.39472(3) 0.55084(7) 0.02251(18) Uani 1 1 d . . . . .
H1 H 0.517(2) 0.4037(8) 0.5791(16) 0.047(5) Uiso 1 1 d . . . . .
O2 O 0.54675(10) 0.29351(4) 0.49208(7) 0.02410(19) Uani 1 1 d . . . . .
N1 N 0.56555(11) 0.21185(4) 0.66272(8) 0.0200(2) Uani 1 1 d . . . . .
N2 N 0.57373(12) 0.17747(4) 0.74873(8) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.5484(19) 0.1881(7) 0.8146(14) 0.030(4) Uiso 1 1 d . . . . .
N3 N 0.23368(11) 0.36174(4) 0.75154(8) 0.0193(2) Uani 1 1 d . . . . .
N4 N -0.01748(12) 0.39505(4) 0.72718(8) 0.0220(2) Uani 1 1 d . . . . .
C1 C 0.36954(13) 0.34400(5) 0.59088(9) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.48384(13) 0.29737(5) 0.57320(9) 0.0201(2) Uani 1 1 d . . . . .
C3 C 0.50126(13) 0.25952(5) 0.66871(9) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.42446(14) 0.28274(5) 0.75912(9) 0.0208(2) Uani 1 1 d . . . . .
H4A H 0.4984(19) 0.2815(6) 0.8356(14) 0.029(4) Uiso 1 1 d . . . . .
H4B H 0.3259(19) 0.2617(6) 0.7627(13) 0.026(4) Uiso 1 1 d . . . . .
C5 C 0.38444(13) 0.34288(5) 0.72227(9) 0.0193(2) Uani 1 1 d . . . . .
C6 C 0.09853(14) 0.37909(5) 0.67766(9) 0.0204(2) Uani 1 1 d . . . . .
C7 C 0.08946(14) 0.37889(5) 0.55429(9) 0.0215(2) Uani 1 1 d . . . . .
H7A H 0.1295(18) 0.4147(7) 0.5335(13) 0.026(4) Uiso 1 1 d . . . . .
H7B H -0.0264(19) 0.3760(6) 0.5164(13) 0.025(4) Uiso 1 1 d . . . . .
C8 C 0.19285(13) 0.33223(5) 0.52229(9) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.63247(13) 0.12413(5) 0.74148(9) 0.0208(2) Uani 1 1 d . . . . .
C10 C 0.64721(16) 0.09038(5) 0.83527(10) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.619(2) 0.1045(7) 0.9016(15) 0.035(4) Uiso 1 1 d . . . . .
C11 C 0.70440(18) 0.03755(6) 0.83099(12) 0.0344(3) Uani 1 1 d . . . . .
H11 H 0.714(2) 0.0139(8) 0.8976(16) 0.043(5) Uiso 1 1 d . . . . .
C12 C 0.74522(18) 0.01764(5) 0.73382(12) 0.0326(3) Uani 1 1 d . . . . .
H12 H 0.785(2) -0.0195(7) 0.7320(14) 0.035(4) Uiso 1 1 d . . . . .
C13 C 0.72939(16) 0.05146(5) 0.64071(11) 0.0284(3) Uani 1 1 d . . . . .
H13 H 0.758(2) 0.0380(7) 0.5717(14) 0.033(4) Uiso 1 1 d . . . . .
C14 C 0.67451(15) 0.10472(5) 0.64374(10) 0.0242(2) Uani 1 1 d . . . . .
H14 H 0.665(2) 0.1289(7) 0.5787(14) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.52261(14) 0.37989(5) 0.77958(10) 0.0235(2) Uani 1 1 d . . . . .
H15A H 0.626(2) 0.3675(7) 0.7609(14) 0.034(4) Uiso 1 1 d . . . . .
H15B H 0.5031(19) 0.4177(7) 0.7567(13) 0.028(4) Uiso 1 1 d . . . . .
H15C H 0.5337(19) 0.3780(7) 0.8623(14) 0.029(4) Uiso 1 1 d . . . . .
C16 C 0.20192(14) 0.36751(5) 0.85870(9) 0.0202(2) Uani 1 1 d . . . . .
C17 C 0.29105(14) 0.35566(5) 0.96593(10) 0.0219(2) Uani 1 1 d . . . . .
H17 H 0.3969(18) 0.3391(6) 0.9797(12) 0.021(3) Uiso 1 1 d . . . . .
C18 C 0.21893(15) 0.36760(5) 1.05530(10) 0.0245(2) Uani 1 1 d . . . . .
H18 H 0.2817(19) 0.3597(6) 1.1326(14) 0.028(4) Uiso 1 1 d . . . . .
C19 C 0.06373(15) 0.38967(5) 1.03924(10) 0.0257(3) Uani 1 1 d . . . . .
H19 H 0.0178(19) 0.3977(6) 1.1051(13) 0.028(4) Uiso 1 1 d . . . . .
C20 C -0.02611(15) 0.40010(5) 0.93236(10) 0.0245(2) Uani 1 1 d . . . . .
H20 H -0.138(2) 0.4150(7) 0.9202(13) 0.030(4) Uiso 1 1 d . . . . .
C21 C 0.04509(14) 0.38877(5) 0.84160(9) 0.0213(2) Uani 1 1 d . . . . .
C22 C 0.12593(14) 0.27635(5) 0.54930(10) 0.0222(2) Uani 1 1 d . . . . .
H22A H 0.1129(18) 0.2744(6) 0.6292(13) 0.022(3) Uiso 1 1 d . . . . .
H22B H 0.2034(18) 0.2473(6) 0.5396(13) 0.025(4) Uiso 1 1 d . . . . .
C23 C -0.03787(15) 0.26237(5) 0.47377(11) 0.0272(3) Uani 1 1 d . . . . .
H23A H -0.123(2) 0.2885(7) 0.4857(14) 0.033(4) Uiso 1 1 d . . . . .
H23B H -0.069(2) 0.2254(7) 0.4918(14) 0.032(4) Uiso 1 1 d . . . . .
C24 C -0.02923(16) 0.26451(6) 0.34997(11) 0.0294(3) Uani 1 1 d . . . . .
H24A H -0.137(2) 0.2558(7) 0.3017(15) 0.038(4) Uiso 1 1 d . . . . .
H24B H 0.0482(19) 0.2353(7) 0.3340(13) 0.027(4) Uiso 1 1 d . . . . .
C25 C 0.03009(15) 0.32027(6) 0.32044(10) 0.0270(3) Uani 1 1 d . . . . .
H25A H -0.053(2) 0.3490(7) 0.3253(14) 0.035(4) Uiso 1 1 d . . . . .
H25B H 0.039(2) 0.3208(7) 0.2413(14) 0.033(4) Uiso 1 1 d . . . . .
C26 C 0.19325(14) 0.33460(5) 0.39553(9) 0.0232(2) Uani 1 1 d . . . . .
H26A H 0.2767(19) 0.3079(7) 0.3801(13) 0.028(4) Uiso 1 1 d . . . . .
H26B H 0.2284(19) 0.3719(7) 0.3783(13) 0.027(4) Uiso 1 1 d . . . . .
O3 O 0.70493(10) 0.44090(3) 0.60832(7) 0.02458(19) Uani 1 1 d . . . . .
H3 H 0.798(3) 0.4250(8) 0.6479(17) 0.052(5) Uiso 1 1 d . . . . .
C27 C 0.72069(19) 0.49855(6) 0.62417(11) 0.0328(3) Uani 1 1 d . . . . .
H27A H 0.620(2) 0.5141(7) 0.5776(15) 0.042(5) Uiso 1 1 d . . . . .
H27B H 0.815(2) 0.5126(8) 0.5945(17) 0.051(5) Uiso 1 1 d . . . . .
C28 C 0.7408(2) 0.51588(6) 0.74527(12) 0.0373(3) Uani 1 1 d . . . . .
H28A H 0.748(2) 0.5569(8) 0.7482(16) 0.047(5) Uiso 1 1 d . . . . .
H28B H 0.641(3) 0.5037(9) 0.7773(18) 0.059(6) Uiso 1 1 d . . . . .
H28C H 0.845(2) 0.5009(8) 0.7902(17) 0.050(5) Uiso 1 1 d . . . . .


_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 H1 0.92(2) . ?
O1 C1 1.4047(13) . ?
O2 C2 1.2218(14) . ?
N1 N2 1.3340(13) . ?
N1 C3 1.2955(15) . ?
N2 H2 0.912(17) . ?
N2 C9 1.4053(15) . ?
N3 C5 1.4726(14) . ?
N3 C6 1.3682(14) . ?
N3 C16 1.3948(14) . ?
N4 C6 1.3172(15) . ?
N4 C21 1.3924(14) . ?
C1 C2 1.5410(15) . ?
C1 C5 1.5797(15) . ?
C1 C8 1.5821(15) . ?
C2 C3 1.4698(15) . ?
C3 C4 1.5041(15) . ?
C4 H4A 1.008(16) . ?
C4 H4B 0.991(16) . ?
C4 C5 1.5541(15) . ?
C5 C15 1.5288(16) . ?
C6 C7 1.4890(15) . ?
C7 H7A 0.990(16) . ?
C7 H7B 0.997(16) . ?
C7 C8 1.5386(15) . ?
C8 C22 1.5413(16) . ?
C8 C26 1.5465(15) . ?
C9 C10 1.3940(16) . ?
C9 C14 1.3963(16) . ?
C10 H10 0.956(17) . ?
C10 C11 1.3846(19) . ?
C11 H11 0.986(19) . ?
C11 C12 1.3896(19) . ?
C12 H12 0.971(17) . ?
C12 C13 1.3874(19) . ?
C13 H13 0.979(17) . ?
C13 C14 1.3861(18) . ?
C14 H14 0.979(17) . ?
C15 H15A 1.001(18) . ?
C15 H15B 0.969(17) . ?
C15 H15C 0.994(16) . ?
C16 C17 1.3958(16) . ?
C16 C21 1.4029(16) . ?
C17 H17 0.967(15) . ?
C17 C18 1.3878(16) . ?
C18 H18 0.999(16) . ?
C18 C19 1.3985(18) . ?
C19 H19 0.983(16) . ?
C19 C20 1.3876(17) . ?
C20 H20 1.001(16) . ?
C20 C21 1.3949(16) . ?
C22 H22A 1.004(15) . ?
C22 H22B 0.991(16) . ?
C22 C23 1.5357(16) . ?
C23 H23A 0.995(17) . ?
C23 H23B 0.981(17) . ?
C23 C24 1.5266(18) . ?
C24 H24A 1.003(18) . ?
C24 H24B 1.017(16) . ?
C24 C25 1.5223(19) . ?
C25 H25A 1.005(18) . ?
C25 H25B 0.984(17) . ?
C25 C26 1.5313(17) . ?
C26 H26A 1.009(16) . ?
C26 H26B 0.995(16) . ?
O3 H3 0.92(2) . ?
O3 C27 1.4251(16) . ?
C27 H27A 0.995(19) . ?
C27 H27B 1.01(2) . ?
C27 C28 1.5102(19) . ?
C28 H28A 1.01(2) . ?
C28 H28B 1.04(2) . ?
C28 H28C 1.01(2) . ?

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
C1 O1 H1 112.2(12) . . ?
C3 N1 N2 118.41(10) . . ?
N1 N2 H2 122.0(10) . . ?
N1 N2 C9 119.73(9) . . ?
C9 N2 H2 118.2(10) . . ?
C6 N3 C5 126.05(9) . . ?
C6 N3 C16 106.53(9) . . ?
C16 N3 C5 127.38(9) . . ?
C6 N4 C21 105.17(9) . . ?
O1 C1 C2 113.14(9) . . ?
O1 C1 C5 113.26(9) . . ?
O1 C1 C8 104.87(9) . . ?
C2 C1 C5 102.14(8) . . ?
C2 C1 C8 110.26(9) . . ?
C5 C1 C8 113.42(9) . . ?
O2 C2 C1 124.41(10) . . ?
O2 C2 C3 127.13(11) . . ?
C3 C2 C1 108.45(9) . . ?
N1 C3 C2 119.69(10) . . ?
N1 C3 C4 129.28(10) . . ?
C2 C3 C4 110.83(10) . . ?
C3 C4 H4A 112.6(9) . . ?
C3 C4 H4B 109.7(9) . . ?
C3 C4 C5 104.32(9) . . ?
H4A C4 H4B 108.1(13) . . ?
C5 C4 H4A 110.6(9) . . ?
C5 C4 H4B 111.6(9) . . ?
N3 C5 C1 110.58(9) . . ?
N3 C5 C4 112.00(9) . . ?
N3 C5 C15 109.03(9) . . ?
C4 C5 C1 105.98(9) . . ?
C15 C5 C1 110.07(9) . . ?
C15 C5 C4 109.14(9) . . ?
N3 C6 C7 121.45(10) . . ?
N4 C6 N3 113.21(10) . . ?
N4 C6 C7 125.34(10) . . ?
C6 C7 H7A 107.9(9) . . ?
C6 C7 H7B 107.7(9) . . ?
C6 C7 C8 110.31(9) . . ?
H7A C7 H7B 107.6(12) . . ?
C8 C7 H7A 110.2(9) . . ?
C8 C7 H7B 112.9(9) . . ?
C7 C8 C1 105.00(9) . . ?
C7 C8 C22 110.35(9) . . ?
C7 C8 C26 110.27(9) . . ?
C22 C8 C1 113.53(9) . . ?
C22 C8 C26 108.95(9) . . ?
C26 C8 C1 108.67(9) . . ?
C10 C9 N2 118.01(10) . . ?
C10 C9 C14 120.21(11) . . ?
C14 C9 N2 121.77(10) . . ?
C9 C10 H10 119.0(10) . . ?
C11 C10 C9 119.55(12) . . ?
C11 C10 H10 121.5(10) . . ?
C10 C11 H11 119.2(11) . . ?
C10 C11 C12 120.73(12) . . ?
C12 C11 H11 120.1(11) . . ?
C11 C12 H12 119.8(10) . . ?
C13 C12 C11 119.30(12) . . ?
C13 C12 H12 120.9(10) . . ?
C12 C13 H13 120.2(10) . . ?
C14 C13 C12 120.89(12) . . ?
C14 C13 H13 118.9(10) . . ?
C9 C14 H14 119.7(10) . . ?
C13 C14 C9 119.31(11) . . ?
C13 C14 H14 121.0(10) . . ?
C5 C15 H15A 110.1(10) . . ?
C5 C15 H15B 111.4(10) . . ?
C5 C15 H15C 109.6(9) . . ?
H15A C15 H15B 109.2(13) . . ?
H15A C15 H15C 108.4(13) . . ?
H15B C15 H15C 108.1(13) . . ?
N3 C16 C17 133.01(11) . . ?
N3 C16 C21 105.21(10) . . ?
C17 C16 C21 121.77(10) . . ?
C16 C17 H17 123.3(9) . . ?
C18 C17 C16 116.70(11) . . ?
C18 C17 H17 119.9(9) . . ?
C17 C18 H18 117.6(9) . . ?
C17 C18 C19 121.94(11) . . ?
C19 C18 H18 120.5(9) . . ?
C18 C19 H19 119.1(9) . . ?
C20 C19 C18 121.18(11) . . ?
C20 C19 H19 119.7(9) . . ?
C19 C20 H20 121.6(9) . . ?
C19 C20 C21 117.62(11) . . ?
C21 C20 H20 120.8(9) . . ?
N4 C21 C16 109.86(10) . . ?
N4 C21 C20 129.39(11) . . ?
C20 C21 C16 120.75(11) . . ?
C8 C22 H22A 111.7(8) . . ?
C8 C22 H22B 109.0(9) . . ?
H22A C22 H22B 107.1(12) . . ?
C23 C22 C8 113.39(10) . . ?
C23 C22 H22A 107.5(9) . . ?
C23 C22 H22B 108.0(9) . . ?
C22 C23 H23A 111.2(10) . . ?
C22 C23 H23B 109.0(10) . . ?
H23A C23 H23B 108.6(14) . . ?
C24 C23 C22 111.06(10) . . ?
C24 C23 H23A 107.9(10) . . ?
C24 C23 H23B 109.0(10) . . ?
C23 C24 H24A 110.1(10) . . ?
C23 C24 H24B 109.4(9) . . ?
H24A C24 H24B 106.6(13) . . ?
C25 C24 C23 110.56(10) . . ?
C25 C24 H24A 111.1(10) . . ?
C25 C24 H24B 109.0(9) . . ?
C24 C25 H25A 110.0(10) . . ?
C24 C25 H25B 110.0(10) . . ?
C24 C25 C26 111.48(10) . . ?
H25A C25 H25B 104.5(13) . . ?
C26 C25 H25A 111.2(10) . . ?
C26 C25 H25B 109.5(10) . . ?
C8 C26 H26A 108.1(9) . . ?
C8 C26 H26B 108.0(9) . . ?
C25 C26 C8 113.38(10) . . ?
C25 C26 H26A 108.8(9) . . ?
C25 C26 H26B 110.9(9) . . ?
H26A C26 H26B 107.4(13) . . ?
C27 O3 H3 107.4(13) . . ?
O3 C27 H27A 104.8(11) . . ?
O3 C27 H27B 110.3(11) . . ?
O3 C27 C28 113.45(11) . . ?
H27A C27 H27B 108.5(15) . . ?
C28 C27 H27A 110.9(10) . . ?
C28 C27 H27B 108.7(12) . . ?
C27 C28 H28A 108.0(11) . . ?
C27 C28 H28B 110.6(12) . . ?
C27 C28 H28C 109.5(11) . . ?
H28A C28 H28B 108.4(16) . . ?
H28A C28 H28C 107.8(16) . . ?
H28B C28 H28C 112.5(16) . . ?

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
O1 H1 O3 0.92(2) 1.81(2) 2.6920(12) 161.4(18) . yes
N2 H2 O2 0.912(17) 2.212(17) 3.1041(12) 166.0(14) 4_566 yes
O3 H3 N4 0.92(2) 1.81(2) 2.7332(13) 179(2) 1_655 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
O1 C1 C2 O2 -35.27(15) . . . . ?
O1 C1 C2 C3 145.13(9) . . . . ?
O1 C1 C5 N3 87.56(11) . . . . ?
O1 C1 C5 C4 -150.86(9) . . . . ?
O1 C1 C5 C15 -32.96(13) . . . . ?
O1 C1 C8 C7 -62.25(10) . . . . ?
O1 C1 C8 C22 177.13(9) . . . . ?
O1 C1 C8 C26 55.73(11) . . . . ?
O2 C2 C3 N1 -12.99(18) . . . . ?
O2 C2 C3 C4 171.71(11) . . . . ?
N1 N2 C9 C10 176.65(11) . . . . ?
N1 N2 C9 C14 -3.71(16) . . . . ?
N1 C3 C4 C5 175.31(11) . . . . ?
N2 N1 C3 C2 -177.24(10) . . . . ?
N2 N1 C3 C4 -2.93(18) . . . . ?
N2 C9 C10 C11 179.88(12) . . . . ?
N2 C9 C14 C13 -178.98(11) . . . . ?
N3 C6 C7 C8 30.70(15) . . . . ?
N3 C16 C17 C18 179.51(12) . . . . ?
N3 C16 C21 N4 0.77(13) . . . . ?
N3 C16 C21 C20 -179.59(11) . . . . ?
N4 C6 C7 C8 -149.00(11) . . . . ?
C1 C2 C3 N1 166.59(10) . . . . ?
C1 C2 C3 C4 -8.70(12) . . . . ?
C1 C8 C22 C23 -173.82(9) . . . . ?
C1 C8 C26 C25 176.40(10) . . . . ?
C2 C1 C5 N3 -150.43(9) . . . . ?
C2 C1 C5 C4 -28.85(11) . . . . ?
C2 C1 C5 C15 89.04(10) . . . . ?
C2 C1 C8 C7 175.65(9) . . . . ?
C2 C1 C8 C22 55.03(12) . . . . ?
C2 C1 C8 C26 -66.37(11) . . . . ?
C2 C3 C4 C5 -9.97(12) . . . . ?
C3 N1 N2 C9 175.58(10) . . . . ?
C3 C4 C5 N3 144.91(9) . . . . ?
C3 C4 C5 C1 24.25(11) . . . . ?
C3 C4 C5 C15 -94.26(10) . . . . ?
C5 N3 C6 N4 -178.31(10) . . . . ?
C5 N3 C6 C7 1.95(17) . . . . ?
C5 N3 C16 C17 -3.8(2) . . . . ?
C5 N3 C16 C21 177.58(10) . . . . ?
C5 C1 C2 O2 -157.35(11) . . . . ?
C5 C1 C2 C3 23.05(11) . . . . ?
C5 C1 C8 C7 61.82(11) . . . . ?
C5 C1 C8 C22 -58.81(12) . . . . ?
C5 C1 C8 C26 179.79(9) . . . . ?
C6 N3 C5 C1 -1.19(15) . . . . ?
C6 N3 C5 C4 -119.15(12) . . . . ?
C6 N3 C5 C15 119.96(12) . . . . ?
C6 N3 C16 C17 178.46(13) . . . . ?
C6 N3 C16 C21 -0.18(12) . . . . ?
C6 N4 C21 C16 -1.07(13) . . . . ?
C6 N4 C21 C20 179.34(12) . . . . ?
C6 C7 C8 C1 -59.04(12) . . . . ?
C6 C7 C8 C22 63.66(12) . . . . ?
C6 C7 C8 C26 -175.93(9) . . . . ?
C7 C8 C22 C23 68.62(12) . . . . ?
C7 C8 C26 C25 -69.01(13) . . . . ?
C8 C1 C2 O2 81.80(13) . . . . ?
C8 C1 C2 C3 -97.80(10) . . . . ?
C8 C1 C5 N3 -31.81(12) . . . . ?
C8 C1 C5 C4 89.77(11) . . . . ?
C8 C1 C5 C15 -152.33(9) . . . . ?
C8 C22 C23 C24 55.88(14) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C9 C14 C13 0.65(18) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C9 -1.0(2) . . . . ?
C14 C9 C10 C11 0.24(19) . . . . ?
C16 N3 C5 C1 -178.54(10) . . . . ?
C16 N3 C5 C4 63.51(14) . . . . ?
C16 N3 C5 C15 -57.39(14) . . . . ?
C16 N3 C6 N4 -0.51(13) . . . . ?
C16 N3 C6 C7 179.75(10) . . . . ?
C16 C17 C18 C19 0.92(18) . . . . ?
C17 C16 C21 N4 -178.06(11) . . . . ?
C17 C16 C21 C20 1.58(18) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C19 C20 C21 -1.20(19) . . . . ?
C19 C20 C21 N4 179.65(12) . . . . ?
C19 C20 C21 C16 0.09(18) . . . . ?
C21 N4 C6 N3 0.97(13) . . . . ?
C21 N4 C6 C7 -179.30(11) . . . . ?
C21 C16 C17 C18 -2.04(17) . . . . ?
C22 C8 C26 C25 52.24(13) . . . . ?
C22 C23 C24 C25 -56.16(14) . . . . ?
C23 C24 C25 C26 56.08(14) . . . . ?
C24 C25 C26 C8 -55.38(14) . . . . ?
C26 C8 C22 C23 -52.58(12) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.287
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KOKBMIMUVQHI
_database_code_depnum_ccdc_archive 'CCDC 2233468'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_KOKBMIMUVQHI        
;
PROBLEM: D-H Bond Without Acceptor  O1       --H1       .     Please Check 
RESPONSE: Disordered peaks of presumably oxygen atoms of water molecules
 with partial occupancies have been deleted by SQUEEZE. A few deleted peaks
 of the residual electron density had been located near the OH group. 
;
_vrf_PLAT094_KOKBMIMUVQHI        
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.31 Report
RESPONSE: Some peaks of the residual electron density could not be completely
 deleted by SQUEEZE, since they are located close to the organic molecule.
 The highest peak of the residual electron density of 0.495 e/A3 may
 correspond to an oxygen atom of a water molecule having a small occupancy.
;
_vrf_PLAT002_KOKBMIMUVQHI        
;
PROBLEM: Number of Distance or Angle Restraints on AtSite          2 Note
RESPONSE: The H-atom of hydroxy group that tends to move to a nearest peak
 of the residual electron density was restrained at a distance of 0.85(2)A.
 Only this distance was restraned.
;
_vrf_PLAT172_KOKBMIMUVQHI        
;
PROBLEM: The CIF-Embedded .res File Contains DFIX Records          1
RESPONSE: The H-atom of hydroxy group that tends to move to a nearest peak
 of the residual electron density was restrained at a distance of 0.85(2)A.
;
_vrf_PLAT605_KOKBMIMUVQHI        
;
PROBLEM: Largest Solvent Accessible VOID in the Structure        461
RESPONSE: Disordered peaks of presumably oxygen atoms of water molecules
 with partial occupancies have been deleted by SQUEEZE.
;
_vrf_PLAT066_KOKBMIMUVQHI        
;
PROBLEM: Predicted and Reported Tmin&Tmax Range Identical          ? 
RESPONSE: The Predicted and Reported Tmin&Tmax were analytically
 calculated from face indexing.
;
# end Validation Reply Form
_audit_creation_date             2022-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N4 O2'
_chemical_formula_sum            'C25 H24 N4 O2'
_chemical_formula_weight         412.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H24 N3 O3'
_chemical_oxdiff_usercomment     KOKBMIMUVQHI
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.1847(2)
_cell_length_b                   9.88774(11)
_cell_length_c                   27.3603(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.5529(13)
_cell_angle_gamma                90
_cell_volume                     4715.65(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21523
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.1870
_cell_measurement_theta_min      3.3510
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0819
0 -1 1 0.0800
0 0 -1 0.0374
0 0 1 0.0579
-2 0 1 0.1266
2 0 -1 0.1479
0 -1 -2 0.0637
0 2 1 0.0943
-1 0 2 0.0943
-1 0 -2 0.0817
1 0 -2 0.1112
1 0 2 0.1129

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
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
0.0005 1.0001 -0.9961 -0.1624 -0.0347 0.0113
-0.0005 -1.0001 0.9961 0.1624 0.0347 -0.0113
0.0001 0.0003 -0.9982 -0.0082 -0.0532 0.0233
-0.0001 -0.0003 0.9982 0.0082 0.0532 -0.0233
-1.9979 0.0001 0.9923 -0.0027 0.0758 0.1516
1.9979 -0.0001 -0.9923 0.0027 -0.0758 -0.1516
-0.0001 -0.9992 -1.9985 0.1379 -0.1247 0.0586
0.0007 1.9993 1.0025 -0.3003 0.0900 -0.0473
-0.9991 -0.0004 1.9935 0.0109 0.1176 0.0408
-0.9986 0.0008 -1.9993 -0.0217 -0.0950 0.1341
0.9991 0.0004 -1.9935 -0.0109 -0.1176 -0.0408
0.9986 -0.0008 1.9993 0.0217 0.0950 -0.1341

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.678
_diffrn_reflns_theta_min         3.370
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -64.80   0.40    0.26    --  -48.51-147.00 -31.00   63
  2  ω    -69.00 -43.00   0.40    0.26    --  -48.51 147.00  18.00   65
  3  ω    -74.00 -48.80   0.40    0.26    --  -48.51 125.00-147.00   63
  4  ω     46.00  71.20   0.40    0.26    --   48.51-125.00 134.00   63
  5  ω     48.80 108.00   0.40    0.26    --   48.51-147.00 -31.00  148
  6  ω    -76.00 -50.80   0.40    0.69    --  -90.00 125.00-147.00   63
  7  ω   -141.00-115.80   0.40    0.69    --  -90.00-125.00 134.00   63
  8  ω    -87.00 -61.80   0.40    0.69    --  -90.00 147.00  18.00   63
  9  ω     80.00 106.00   0.40    0.69    --  111.50 147.00  18.00   65
 10  ω     99.00 157.00   0.40    0.69    --  111.50 125.00-147.00  145
 11  ω     88.00 126.00   0.40    0.69    --  111.50-147.00 -31.00   95
 12  ω     70.00 110.00   0.40    0.69    --  111.50-125.00 134.00  100
 13  ω   -119.00 -75.80   0.40    0.26    --  -48.51-125.00-150.00  108
 14  ω   -120.00 -28.80   0.40    0.26    --  -48.51 -77.00 120.00  228
 15  ω   -120.00 -94.80   0.40    0.26    --  -48.51-125.00 -60.00   63
 16  ω    -25.00  25.00   0.40    0.26    --  -48.51  19.00-150.00  125
 17  ω    -11.20  26.00   0.40    0.26    --  -48.51  19.00 150.00   93
 18  ω    -12.00  23.20   0.40    0.26    --   48.51 -38.00-120.00   88
 19  ω    -50.00 -18.80   0.40    0.69    --  -90.00  45.00  60.00   78
 20  ω     72.00 104.00   0.40    0.69    --  111.50 -95.00 -28.97   80
 21  ω     46.00  74.00   0.40    0.69    --  111.50 -85.00-154.10   70
 22  ω     41.00  69.00   0.40    0.69    --  111.50 -95.00 -28.97   70
 23  ω    103.00 176.20   0.40    0.69    --  111.50  45.00 -30.00  183
 24  ω     42.00 106.00   0.40    0.69    --  111.50-105.00 -45.54  160
 25  ω     41.00  66.20   0.40    0.69    --  111.50 -61.00  90.00   63
 26  ω     40.00  66.00   0.40    0.69    --  111.50 -57.00 -27.00   65
 27  ω     41.00  78.20   0.40    0.69    --  111.50 -77.00 150.00   93
 28  ω     46.00 103.20   0.40    0.69    --  111.50-102.00 126.30  143
 29  ω     92.00 125.20   0.40    0.69    --  111.50-145.00 128.42   83
 30  ω     99.00 169.00   0.40    0.69    --  111.50 125.00 150.00  175
 31  ω     80.00 118.00   0.40    0.69    --  111.50-134.00-101.61   95
 32  ω     40.00  72.00   0.40    0.69    --  111.50 -77.00 -30.00   80
 33  ω     41.00  70.20   0.40    0.69    --  111.50-125.00 150.00   73
 34  ω     89.00 116.20   0.40    0.69    --  111.50 -85.00-154.10   68
 35  ω    114.00 152.00   0.40    0.69    --  111.50  77.00 150.00   95
 36  ω    104.00 140.00   0.40    0.69    --  111.50  45.00   0.00   90
 37  ω    144.00 170.00   0.40    0.69    --  111.50  45.00   0.00   65
 38  ω     40.00 106.00   0.40    0.69    --  111.50-119.00 -42.05  165
 39  ω     41.00  74.20   0.40    0.69    --  111.50-125.00-180.00   83
 40  ω     44.00  85.20   0.40    0.69    --  111.50 -77.00-150.00  103
 41  ω    143.00 169.00   0.40    0.69    --  111.50  30.00 120.00   65
 42  ω     53.00  78.20   0.40    0.69    --  111.50-145.00 128.42   63
 43  ω    103.00 130.20   0.40    0.69    --  111.50  45.00  30.00   68
 44  ω     95.00 157.00   0.40    0.69    --  111.50 125.00   0.00  155
 45  ω     41.00  70.20   0.40    0.69    --  111.50 -61.00  30.00   73
 46  ω     73.00 101.00   0.40    0.69    --  111.50 -95.00-180.00   70
 47  ω    135.00 177.00   0.40    0.69    --  111.50 125.00 120.00  105
 48  ω     47.00  76.20   0.40    0.69    --  111.50 -77.00 -60.00   73
 49  ω    116.80 178.00   0.40    0.69    --  111.50  77.00-150.00  153
 50  ω    141.00 166.20   0.40    0.69    --  111.50  15.00 150.00   63
 51  ω    130.00 156.00   0.40    0.69    --  111.50  45.00 120.00   65
 52  ω     66.00 102.00   0.40    0.69    --  111.50 -77.00  30.00   90
 53  ω     42.00  70.00   0.40    0.69    --  111.50-125.00 -60.00   70
 54  ω     70.00 111.20   0.40    0.69    --  111.50 -81.00 -93.69  103
 55  ω    122.00 162.00   0.40    0.69    --  111.50  30.00  30.00  100
 56  ω     42.00  69.20   0.40    0.69    --  111.50 -61.00   0.00   68
 57  ω     42.00  69.20   0.40    0.69    --  111.50 -61.00  60.00   68
 58  ω     79.00 105.00   0.40    0.69    --  111.50-107.00   4.97   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0053788000
_diffrn_orient_matrix_UB_12      -0.1542623000
_diffrn_orient_matrix_UB_13      0.0081221000
_diffrn_orient_matrix_UB_21      -0.0114660000
_diffrn_orient_matrix_UB_22      0.0183202000
_diffrn_orient_matrix_UB_23      0.0532610000
_diffrn_orient_matrix_UB_31      -0.0874810000
_diffrn_orient_matrix_UB_32      -0.0119180000
_diffrn_orient_matrix_UB_33      -0.0233790000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4797
_reflns_number_total             5013
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00065(6)
_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   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.092
_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)+(0.0481P)²+9.2106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1413
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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 0.42891(9) 0.83739(13) 0.63706(6) 0.0368(3) Uani 1 1 d D . . . .
H1 H 0.4484(15) 0.864(3) 0.6125(9) 0.055 Uiso 1 1 d D U . . .
O2 O 0.24244(7) 0.50922(13) 0.67815(5) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.50410(9) 0.70026(16) 0.80988(7) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.53633(9) 0.67009(15) 0.73735(6) 0.0289(3) Uani 1 1 d . . . . .
N3 N 0.49973(9) 0.41767(15) 0.58039(6) 0.0281(3) Uani 1 1 d . . . . .
N4 N 0.38260(9) 0.61931(16) 0.55930(6) 0.0317(4) Uani 1 1 d . . . . .
C1 C 0.44163(10) 0.69910(17) 0.64924(8) 0.0280(4) Uani 1 1 d . . . . .
C2 C 0.38137(10) 0.66040(17) 0.67819(7) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.40346(11) 0.74404(19) 0.72771(8) 0.0302(4) Uani 1 1 d . . . . .
H3A H 0.3663(13) 0.734(2) 0.7488(9) 0.033(6) Uiso 1 1 d . . . . .
H3B H 0.4010(13) 0.841(2) 0.7188(9) 0.031(6) Uiso 1 1 d . . . . .
C4 C 0.48102(10) 0.70614(18) 0.75984(8) 0.0291(4) Uani 1 1 d . . . . .
C5 C 0.52812(10) 0.67131(18) 0.68225(8) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.55009(10) 0.5306(2) 0.66489(8) 0.0304(4) Uani 1 1 d . . . . .
H6A H 0.5424(13) 0.457(3) 0.6888(9) 0.037(6) Uiso 1 1 d . . . . .
H6B H 0.6049(13) 0.527(2) 0.6646(9) 0.034(6) Uiso 1 1 d . . . . .
C7 C 0.49545(10) 0.51208(17) 0.61310(7) 0.0263(4) Uani 1 1 d . . . . .
C8 C 0.43569(10) 0.61029(18) 0.60299(7) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.58060(12) 0.7814(2) 0.67153(9) 0.0368(5) Uani 1 1 d . . . . .
H9A H 0.6370(16) 0.757(3) 0.6885(10) 0.047(7) Uiso 1 1 d . . . . .
H9B H 0.5701(13) 0.787(3) 0.6321(10) 0.040(6) Uiso 1 1 d . . . . .
H9C H 0.5685(14) 0.875(3) 0.6845(10) 0.043(7) Uiso 1 1 d . . . . .
C10 C 0.58076(11) 0.66045(18) 0.82184(8) 0.0312(4) Uani 1 1 d . . . . .
C11 C 0.63415(12) 0.6431(2) 0.86941(9) 0.0363(4) Uani 1 1 d . . . . .
H11 H 0.6188(19) 0.659(3) 0.8994(13) 0.073(10) Uiso 1 1 d . . . . .
C12 C 0.70746(12) 0.6020(2) 0.87066(9) 0.0385(5) Uani 1 1 d . . . . .
H12 H 0.7478(14) 0.592(3) 0.9050(10) 0.041(6) Uiso 1 1 d . . . . .
C13 C 0.72690(11) 0.5769(2) 0.82548(9) 0.0363(5) Uani 1 1 d . . . . .
H13 H 0.7806(13) 0.545(2) 0.8282(8) 0.033(6) Uiso 1 1 d . . . . .
C14 C 0.67511(11) 0.59455(19) 0.77779(9) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.6892(14) 0.575(3) 0.7466(10) 0.042(7) Uiso 1 1 d . . . . .
C15 C 0.60188(11) 0.63864(18) 0.77689(8) 0.0300(4) Uani 1 1 d . . . . .
C16 C 0.44299(11) 0.41876(19) 0.53536(8) 0.0296(4) Uani 1 1 d . . . . .
C17 C 0.43956(12) 0.3147(2) 0.49955(8) 0.0339(4) Uani 1 1 d . . . . .
H17 H 0.4810(14) 0.241(3) 0.5099(9) 0.042(7) Uiso 1 1 d . . . . .
C18 C 0.38182(14) 0.3124(3) 0.45479(9) 0.0427(5) Uani 1 1 d . . . . .
H18 H 0.3806(15) 0.237(3) 0.4317(10) 0.047(7) Uiso 1 1 d . . . . .
C19 C 0.32698(14) 0.4174(3) 0.44267(9) 0.0482(6) Uani 1 1 d . . . . .
H19 H 0.2864(16) 0.425(3) 0.4088(11) 0.056(8) Uiso 1 1 d . . . . .
C20 C 0.32959(13) 0.5205(3) 0.47638(9) 0.0457(5) Uani 1 1 d . . . . .
H20 H 0.2878(15) 0.590(3) 0.4683(9) 0.044(7) Uiso 1 1 d . . . . .
C21 C 0.38555(11) 0.5219(2) 0.52399(8) 0.0325(4) Uani 1 1 d . . . . .
C22 C 0.30036(11) 0.69945(19) 0.64575(8) 0.0300(4) Uani 1 1 d . . . . .
H22A H 0.2928(14) 0.659(3) 0.6120(10) 0.039(6) Uiso 1 1 d . . . . .
H22B H 0.2959(13) 0.799(3) 0.6414(9) 0.038(6) Uiso 1 1 d . . . . .
C23 C 0.23879(11) 0.6517(2) 0.66963(9) 0.0330(4) Uani 1 1 d . . . . .
H23A H 0.2427(13) 0.700(2) 0.7034(9) 0.033(6) Uiso 1 1 d . . . . .
H23B H 0.1894(13) 0.669(2) 0.6462(9) 0.032(6) Uiso 1 1 d . . . . .
C24 C 0.31519(10) 0.47035(19) 0.71136(8) 0.0303(4) Uani 1 1 d . . . . .
H24A H 0.3134(12) 0.366(2) 0.7149(8) 0.028(5) Uiso 1 1 d . . . . .
H24B H 0.3240(13) 0.514(2) 0.7468(9) 0.036(6) Uiso 1 1 d . . . . .
C25 C 0.38067(10) 0.50747(18) 0.68945(8) 0.0267(4) Uani 1 1 d . . . . .
H25A H 0.3720(12) 0.456(2) 0.6569(9) 0.028(5) Uiso 1 1 d . . . . .
H25B H 0.4292(13) 0.479(2) 0.7140(9) 0.032(6) Uiso 1 1 d . . . . .


_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 H1 0.884(17) . ?
O1 C1 1.411(2) . ?
O2 C23 1.426(2) . ?
O2 C24 1.428(2) . ?
N1 C4 1.314(3) . ?
N1 C10 1.395(3) . ?
N2 C4 1.368(2) . ?
N2 C5 1.472(3) . ?
N2 C15 1.398(3) . ?
N3 C7 1.311(2) . ?
N3 C16 1.363(2) . ?
N4 C8 1.308(3) . ?
N4 C21 1.376(3) . ?
C1 C2 1.571(3) . ?
C1 C5 1.599(3) . ?
C1 C8 1.519(3) . ?
C2 C3 1.540(3) . ?
C2 C22 1.537(3) . ?
C2 C25 1.544(2) . ?
C3 H3A 1.01(2) . ?
C3 H3B 0.99(2) . ?
C3 C4 1.482(3) . ?
C5 C6 1.559(3) . ?
C5 C9 1.530(3) . ?
C6 H6A 1.01(3) . ?
C6 H6B 1.00(2) . ?
C6 C7 1.492(3) . ?
C7 C8 1.425(2) . ?
C9 H9A 1.03(3) . ?
C9 H9B 1.04(3) . ?
C9 H9C 1.04(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.406(3) . ?
C11 H11 0.95(3) . ?
C11 C12 1.385(3) . ?
C12 H12 1.02(3) . ?
C12 C13 1.401(3) . ?
C13 H13 1.01(2) . ?
C13 C14 1.386(3) . ?
C14 H14 0.98(3) . ?
C14 C15 1.395(3) . ?
C16 C17 1.410(3) . ?
C16 C21 1.429(3) . ?
C17 H17 1.03(3) . ?
C17 C18 1.367(3) . ?
C18 H18 0.97(3) . ?
C18 C19 1.412(4) . ?
C19 H19 1.01(3) . ?
C19 C20 1.366(4) . ?
C20 H20 1.00(3) . ?
C20 C21 1.406(3) . ?
C22 H22A 0.98(3) . ?
C22 H22B 0.99(3) . ?
C22 C23 1.523(3) . ?
C23 H23A 1.03(2) . ?
C23 H23B 0.96(2) . ?
C24 H24A 1.03(2) . ?
C24 H24B 1.03(2) . ?
C24 C25 1.523(3) . ?
C25 H25A 1.00(2) . ?
C25 H25B 0.99(2) . ?

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
C1 O1 H1 113.0(19) . . ?
C23 O2 C24 111.19(14) . . ?
C4 N1 C10 104.96(16) . . ?
C4 N2 C5 125.85(16) . . ?
C4 N2 C15 106.50(16) . . ?
C15 N2 C5 127.59(16) . . ?
C7 N3 C16 115.75(16) . . ?
C8 N4 C21 115.32(16) . . ?
O1 C1 C2 105.32(14) . . ?
O1 C1 C5 111.63(15) . . ?
O1 C1 C8 113.32(16) . . ?
C2 C1 C5 112.86(15) . . ?
C8 C1 C2 112.64(14) . . ?
C8 C1 C5 101.32(14) . . ?
C3 C2 C1 105.56(14) . . ?
C3 C2 C25 111.43(16) . . ?
C22 C2 C1 109.82(16) . . ?
C22 C2 C3 109.88(15) . . ?
C22 C2 C25 107.47(14) . . ?
C25 C2 C1 112.68(14) . . ?
C2 C3 H3A 113.6(13) . . ?
C2 C3 H3B 108.9(13) . . ?
H3A C3 H3B 104.1(18) . . ?
C4 C3 C2 110.60(15) . . ?
C4 C3 H3A 108.4(13) . . ?
C4 C3 H3B 111.2(13) . . ?
N1 C4 N2 113.57(17) . . ?
N1 C4 C3 126.64(18) . . ?
N2 C4 C3 119.78(18) . . ?
N2 C5 C1 112.11(15) . . ?
N2 C5 C6 110.17(16) . . ?
N2 C5 C9 108.38(15) . . ?
C6 C5 C1 106.12(14) . . ?
C9 C5 C1 109.66(16) . . ?
C9 C5 C6 110.41(16) . . ?
C5 C6 H6A 110.4(14) . . ?
C5 C6 H6B 112.1(14) . . ?
H6A C6 H6B 107.5(19) . . ?
C7 C6 C5 103.87(15) . . ?
C7 C6 H6A 110.4(14) . . ?
C7 C6 H6B 112.6(13) . . ?
N3 C7 C6 125.64(16) . . ?
N3 C7 C8 122.90(17) . . ?
C8 C7 C6 111.45(16) . . ?
N4 C8 C1 125.50(16) . . ?
N4 C8 C7 123.20(17) . . ?
C7 C8 C1 111.29(16) . . ?
C5 C9 H9A 110.3(15) . . ?
C5 C9 H9B 107.1(14) . . ?
C5 C9 H9C 111.4(14) . . ?
H9A C9 H9B 110(2) . . ?
H9A C9 H9C 110(2) . . ?
H9B C9 H9C 108(2) . . ?
N1 C10 C15 110.00(17) . . ?
C11 C10 N1 129.57(19) . . ?
C11 C10 C15 120.43(19) . . ?
C10 C11 H11 119(2) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 123(2) . . ?
C11 C12 H12 119.1(14) . . ?
C11 C12 C13 120.9(2) . . ?
C13 C12 H12 120.0(14) . . ?
C12 C13 H13 118.1(13) . . ?
C14 C13 C12 122.3(2) . . ?
C14 C13 H13 119.6(13) . . ?
C13 C14 H14 121.3(15) . . ?
C13 C14 C15 116.5(2) . . ?
C15 C14 H14 122.2(15) . . ?
N2 C15 C10 104.95(16) . . ?
C14 C15 N2 133.05(19) . . ?
C14 C15 C10 122.01(19) . . ?
N3 C16 C17 119.64(17) . . ?
N3 C16 C21 121.37(17) . . ?
C17 C16 C21 118.98(18) . . ?
C16 C17 H17 116.1(14) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 123.5(14) . . ?
C17 C18 H18 117.7(16) . . ?
C17 C18 C19 120.6(2) . . ?
C19 C18 H18 121.7(16) . . ?
C18 C19 H19 123.4(17) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 116.3(17) . . ?
C19 C20 H20 119.1(15) . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 120.0(15) . . ?
N4 C21 C16 121.25(18) . . ?
N4 C21 C20 119.67(19) . . ?
C20 C21 C16 119.05(19) . . ?
C2 C22 H22A 107.2(14) . . ?
C2 C22 H22B 110.5(14) . . ?
H22A C22 H22B 108(2) . . ?
C23 C22 C2 112.03(16) . . ?
C23 C22 H22A 110.8(14) . . ?
C23 C22 H22B 108.4(14) . . ?
O2 C23 C22 111.77(15) . . ?
O2 C23 H23A 109.1(13) . . ?
O2 C23 H23B 105.9(14) . . ?
C22 C23 H23A 111.8(13) . . ?
C22 C23 H23B 108.8(14) . . ?
H23A C23 H23B 109.3(19) . . ?
O2 C24 H24A 106.2(12) . . ?
O2 C24 H24B 110.7(13) . . ?
O2 C24 C25 111.80(16) . . ?
H24A C24 H24B 109.1(18) . . ?
C25 C24 H24A 109.0(12) . . ?
C25 C24 H24B 109.9(13) . . ?
C2 C25 H25A 109.3(13) . . ?
C2 C25 H25B 111.1(14) . . ?
C24 C25 C2 111.50(15) . . ?
C24 C25 H25A 106.6(12) . . ?
C24 C25 H25B 108.1(13) . . ?
H25A C25 H25B 110.3(18) . . ?

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
O1 C1 C2 C3 -64.53(18) . . . . ?
O1 C1 C2 C22 53.87(19) . . . . ?
O1 C1 C2 C25 173.64(15) . . . . ?
O1 C1 C5 N2 94.86(18) . . . . ?
O1 C1 C5 C6 -144.83(16) . . . . ?
O1 C1 C5 C9 -25.6(2) . . . . ?
O1 C1 C8 N4 -43.7(2) . . . . ?
O1 C1 C8 C7 137.17(16) . . . . ?
O2 C24 C25 C2 57.2(2) . . . . ?
N1 C10 C11 C12 179.84(19) . . . . ?
N1 C10 C15 N2 1.6(2) . . . . ?
N1 C10 C15 C14 -178.31(16) . . . . ?
N2 C5 C6 C7 143.73(15) . . . . ?
N3 C7 C8 N4 -3.9(3) . . . . ?
N3 C7 C8 C1 175.21(16) . . . . ?
N3 C16 C17 C18 178.25(19) . . . . ?
N3 C16 C21 N4 -4.0(3) . . . . ?
N3 C16 C21 C20 178.20(19) . . . . ?
C1 C2 C3 C4 -62.52(19) . . . . ?
C1 C2 C22 C23 174.37(15) . . . . ?
C1 C2 C25 C24 -172.77(16) . . . . ?
C1 C5 C6 C7 22.16(19) . . . . ?
C2 C1 C5 N2 -23.5(2) . . . . ?
C2 C1 C5 C6 96.77(17) . . . . ?
C2 C1 C5 C9 -143.97(16) . . . . ?
C2 C1 C8 N4 75.7(2) . . . . ?
C2 C1 C8 C7 -103.40(17) . . . . ?
C2 C3 C4 N1 -144.17(18) . . . . ?
C2 C3 C4 N2 34.5(2) . . . . ?
C2 C22 C23 O2 -56.6(2) . . . . ?
C3 C2 C22 C23 -69.9(2) . . . . ?
C3 C2 C25 C24 68.8(2) . . . . ?
C4 N1 C10 C11 177.34(19) . . . . ?
C4 N1 C10 C15 -1.8(2) . . . . ?
C4 N2 C5 C1 -8.6(2) . . . . ?
C4 N2 C5 C6 -126.54(18) . . . . ?
C4 N2 C5 C9 112.56(19) . . . . ?
C4 N2 C15 C10 -0.75(19) . . . . ?
C4 N2 C15 C14 179.16(19) . . . . ?
C5 N2 C4 N1 -177.79(16) . . . . ?
C5 N2 C4 C3 3.4(3) . . . . ?
C5 N2 C15 C10 176.57(16) . . . . ?
C5 N2 C15 C14 -3.5(3) . . . . ?
C5 C1 C2 C3 57.49(18) . . . . ?
C5 C1 C2 C22 175.89(14) . . . . ?
C5 C1 C2 C25 -64.3(2) . . . . ?
C5 C1 C8 N4 -163.44(17) . . . . ?
C5 C1 C8 C7 17.45(19) . . . . ?
C5 C6 C7 N3 168.95(17) . . . . ?
C5 C6 C7 C8 -11.8(2) . . . . ?
C6 C7 C8 N4 176.79(17) . . . . ?
C6 C7 C8 C1 -4.1(2) . . . . ?
C7 N3 C16 C17 -175.03(17) . . . . ?
C7 N3 C16 C21 3.6(3) . . . . ?
C8 N4 C21 C16 0.3(3) . . . . ?
C8 N4 C21 C20 178.10(19) . . . . ?
C8 C1 C2 C3 171.49(15) . . . . ?
C8 C1 C2 C22 -70.11(19) . . . . ?
C8 C1 C2 C25 49.7(2) . . . . ?
C8 C1 C5 N2 -144.23(15) . . . . ?
C8 C1 C5 C6 -23.92(18) . . . . ?
C8 C1 C5 C9 95.33(17) . . . . ?
C9 C5 C6 C7 -96.60(18) . . . . ?
C10 N1 C4 N2 1.4(2) . . . . ?
C10 N1 C4 C3 -179.88(17) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C10 C15 N2 -177.67(16) . . . . ?
C11 C10 C15 C14 2.4(3) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 N2 178.35(18) . . . . ?
C13 C14 C15 C10 -1.8(3) . . . . ?
C15 N2 C4 N1 -0.4(2) . . . . ?
C15 N2 C4 C3 -179.24(16) . . . . ?
C15 N2 C5 C1 174.56(16) . . . . ?
C15 N2 C5 C6 56.6(2) . . . . ?
C15 N2 C5 C9 -64.3(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C16 N3 C7 C6 179.30(17) . . . . ?
C16 N3 C7 C8 0.1(3) . . . . ?
C16 C17 C18 C19 3.1(3) . . . . ?
C17 C16 C21 N4 174.60(18) . . . . ?
C17 C16 C21 C20 -3.2(3) . . . . ?
C17 C18 C19 C20 -2.2(4) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 N4 -173.7(2) . . . . ?
C19 C20 C21 C16 4.1(3) . . . . ?
C21 N4 C8 C1 -175.59(17) . . . . ?
C21 N4 C8 C7 3.4(3) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
C22 C2 C3 C4 179.13(16) . . . . ?
C22 C2 C25 C24 -51.7(2) . . . . ?
C23 O2 C24 C25 -60.1(2) . . . . ?
C24 O2 C23 C22 59.6(2) . . . . ?
C25 C2 C3 C4 60.1(2) . . . . ?
C25 C2 C22 C23 51.5(2) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 6.161
_oxdiff_exptl_absorpt_empirical_full_min 0.632
