# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_kor_5_100_1
_database_code_depnum_ccdc_archive 'CCDC 2076671'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(7aR,13S,13aS,14R)-13a-nitro-13-(pyridin-2-yl)-14-(p-tolyl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-on
_chemical_name_common            
(7aR,13S,13aS,14R)-13a-nitro-13-(pyridin-2-yl)-14-(p-tolyl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-on
_chemical_formula_moiety         'C2 H6 O S, C29 H24 N4 O4'
_chemical_formula_sum            'C31 H30 N4 O5 S'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         570.65
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C c'
_symmetry_int_tables_number      9
_chemical_absolute_configuration .
_exptl_crystal_recrystallization_method 'From DMSO'
_chemical_melting_point          461-462
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C31 H30 N4 O5 S'
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'
S S 0.3331 0.5567 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.55130(10)
_cell_length_b                   17.20680(10)
_cell_length_c                   14.50100(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.9860(10)
_cell_angle_gamma                90
_cell_volume                     2756.50(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21633
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3320
_cell_measurement_theta_min      3.1420
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    1.449
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -2 5 0.1454
-6 -6 6 0.1250
-4 -8 4 0.1184
2 -11 0 0.0992
7 -5 -4 0.1358
7 4 0 0.1318
4 7 4 0.1312
-2 3 -8 0.1406
2 6 6 0.1465
-1 -11 1 0.0927
1 -11 -1 0.0973
2 -3 8 0.1767
3 -10 -2 0.1144
-3 10 4 0.1124
4 -6 4 0.1513
-6 4 7 0.1256
6 -5 -5 0.1406
1 11 0 0.0816
7 0 -4 0.1225
0 11 0 0.0715

_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.178
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
-6.9611 -2.4462 5.2548 -0.7551 -0.6465 0.1086
-5.5902 -5.9446 5.6647 -0.4926 -0.8070 0.3259
-4.4110 -8.4463 4.2019 -0.2202 -0.9241 0.3124
1.5469 -10.9135 -0.1448 0.6129 -0.7151 0.3362
6.5601 -4.7461 -4.4818 0.9915 0.0792 0.1028
6.7195 3.7317 0.1612 0.4751 0.7787 0.4098
3.8684 6.6368 4.1323 -0.0671 0.8277 0.5571
-1.8492 2.6699 -7.7773 0.0028 -0.0089 -1.0000
2.1822 5.9900 6.3280 -0.2823 0.6759 0.6808
-0.7411 -11.0948 0.7875 0.3682 -0.8880 0.2753
1.3642 -10.9531 -1.1093 0.6333 -0.7408 0.2237
1.7888 -2.6953 7.8129 -0.0088 0.0029 1.0000
3.4696 -9.7888 -2.4422 0.8342 -0.5106 0.2082
-3.2906 9.6017 3.5434 -0.8505 0.5203 -0.0767
4.3630 -6.4574 3.5486 0.5542 -0.1343 0.8214
-5.9938 3.9381 6.5704 -0.9818 -0.0786 0.1727
6.4212 -4.5124 -5.2384 0.9968 0.0794 0.0090
0.8942 11.0861 -0.1757 -0.3762 0.9046 -0.2006
7.4124 -0.4106 -4.0228 0.8724 0.4750 0.1149
0.1721 11.1499 0.3843 -0.4685 0.8617 -0.1948

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28113
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.510
_diffrn_reflns_theta_min         4.757
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00-180.00   99
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00  90.00   99
  3  ω      6.00  82.00   1.00    1.00    --   41.35 -99.00  30.00   76
  4  ω      6.00  32.00   1.00    1.00    --   41.35  85.00 170.22   26
  5  ω      6.00  32.00   1.00    1.00    --   41.35  85.00-153.24   26
  6  ω    103.00 178.00   1.00    1.55    --  112.00  77.00  90.00   75
  7  ω     36.00 109.00   1.00    1.55    --  112.00-111.00 150.00   73
  8  ω    103.00 178.00   1.00    1.55    --  112.00  77.00 -60.00   75
  9  ω     40.00 141.00   1.00    1.55    --  112.00 -61.00 120.00  101
 10  ω    103.00 178.00   1.00    1.55    --  112.00  77.00-120.00   75
 11  ω     59.00 178.00   1.00    1.55    --  112.00  15.00 -60.00  119
 12  ω     36.00 109.00   1.00    1.55    --  112.00-111.00-150.00   73
 13  ω     36.00 109.00   1.00    1.55    --  112.00-111.00  90.00   73
 14  ω     39.00 138.00   1.00    1.55    --  112.00 -45.00  30.00   99
 15  ω     36.00 109.00   1.00    1.55    --  112.00-111.00 -30.00   73
 16  ω    104.00 178.00   1.00    1.55    --  112.00 111.00 150.00   74
 17  ω     36.00 140.00   1.00    1.55    --  112.00 -30.00  90.00  104
 18  ω     34.00 108.00   1.00    1.55    --  112.00-106.00  71.00   74
 19  ω    103.00 178.00   1.00    1.55    --  112.00  77.00-180.00   75
 20  ω     30.00 100.00   1.00    1.55    --  112.00 -95.00-180.00   70
 21  ω     35.00 100.00   1.00    1.55    --  112.00 -95.00  90.00   65
 22  ω     73.00 102.00   1.00    1.55    --  112.00 -95.00 150.00   29
 23  ω     62.00 141.00   1.00    1.55    --  112.00 178.00  90.00   79
 24  ω   -107.00 -26.00   1.00    1.00    --  -41.60 -57.00 -30.00   81
 25  ω     -8.00  29.00   1.00    1.00    --   41.60 -77.00-120.00   37
 26  ω      8.00  33.00   1.00    1.00    --   41.60  80.00 -64.70   25
 27  ω      9.00  35.00   1.00    1.00    --   41.60 -38.00  30.00   26
 28  ω      7.00  34.00   1.00    1.00    --   41.60  83.00 -38.13   27
 29  ω     28.00  78.00   1.00    1.00    --   41.60-125.00-120.00   50
 30  ω    116.00 144.00   1.00    1.55    --  112.00 111.00-150.00   28
 31  ω     77.00 106.00   1.00    1.55    --  112.00-111.00 -60.00   29
 32  ω     49.00  75.00   1.00    1.55    --  112.00   0.00   0.00   26
 33  ω     42.00  68.00   1.00    1.55    --  112.00-111.00  30.00   26
 34  ω     76.00 107.00   1.00    1.55    --  112.00-111.00  30.00   31
 35  ω     36.00  82.00   1.00    1.55    --  112.00 -95.00-150.00   46
 36  ω    144.00 169.00   1.00    1.55    --  112.00  77.00 120.00   25
 37  ω    113.00 169.00   1.00    1.55    --  112.00  77.00-150.00   56
 38  ω    120.00 145.00   1.00    1.55    --  112.00 -77.00  30.00   25
 39  ω     71.00 109.00   1.00    1.55    --  112.00-111.00 -90.00   38
 40  ω     50.00  76.00   1.00    1.55    --  112.00 -77.00  30.00   26
 41  ω     50.00  94.00   1.00    1.55    --  112.00 -95.00  30.00   44
 42  ω    112.00 146.00   1.00    1.55    --  112.00 178.00  30.00   34
 43  ω    104.00 131.00   1.00    1.55    --  112.00  30.00 150.00   27
 44  ω     91.00 117.00   1.00    1.55    --  112.00 -45.00 120.00   26
 45  ω     83.00 109.00   1.00    1.55    --  112.00-111.00-180.00   26
 46  ω    138.00 164.00   1.00    1.55    --  112.00 111.00 -30.00   26
 47  ω     75.00 101.00   1.00    1.55    --  112.00 -15.00   0.00   26
 48  ω    124.00 150.00   1.00    1.55    --  112.00 -15.00   0.00   26
 49  ω     84.00 109.00   1.00    1.55    --  112.00-111.00   0.00   25
 50  ω    104.00 172.00   1.00    1.55    --  112.00  77.00  60.00   68
 51  ω    122.00 148.00   1.00    1.55    --  112.00 106.00 170.00   26
 52  ω    119.00 145.00   1.00    1.55    --  112.00  45.00 -30.00   26
 53  ω     45.00  71.00   1.00    1.55    --  112.00 -61.00 -60.00   26
 54  ω    121.00 146.00   1.00    1.55    --  112.00 178.00-150.00   25
 55  ω     82.00 108.00   1.00    1.55    --  112.00-111.00-120.00   26
 56  ω    116.00 141.00   1.00    1.55    --  112.00 -61.00 -60.00   25
 57  ω    132.00 171.00   1.00    1.55    --  112.00 111.00  30.00   39
 58  ω    109.00 135.00   1.00    1.55    --  112.00  77.00   0.00   26
 59  ω    153.00 178.00   1.00    1.55    --  112.00  77.00   0.00   25
 60  ω     70.00  96.00   1.00    1.55    --  112.00 -95.00-120.00   26
 61  ω     81.00 106.00   1.00    1.55    --  112.00 -95.00 120.00   25
 62  ω     54.00  92.00   1.00    1.55    --  112.00 -45.00-150.00   38
 63  ω    146.00 171.00   1.00    1.55    --  112.00  61.00 -90.00   25
 64  ω    143.00 169.00   1.00    1.55    --  112.00  61.00 -30.00   26
 65  ω     93.00 119.00   1.00    1.55    --  112.00   0.00   0.00   26
 66  ω     99.00 140.00   1.00    1.55    --  112.00 -71.00 -46.76   41
 67  ω     69.00  95.00   1.00    1.55    --  112.00 -61.00   0.00   26
 68  ω     59.00  85.00   1.00    1.55    --  112.00 -24.00-164.89   26
 69  ω     68.00  94.00   1.00    1.55    --  112.00 -49.00  61.54   26
 70  ω   -116.00 -17.00   1.00    1.00    --  -41.60 -38.00   0.00   99
 71  ω    -66.00 -13.00   1.00    1.00    --  -41.60  38.00 150.00   53
 72  ω      8.00  42.00   1.00    1.00    --   41.60  81.00  81.81   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0950390000
_diffrn_orient_matrix_UB_12      -0.0421930000
_diffrn_orient_matrix_UB_13      -0.0374453000
_diffrn_orient_matrix_UB_21      0.0735444000
_diffrn_orient_matrix_UB_22      0.0758167000
_diffrn_orient_matrix_UB_23      0.0096858000
_diffrn_orient_matrix_UB_31      0.0707921000
_diffrn_orient_matrix_UB_32      -0.0221528000
_diffrn_orient_matrix_UB_33      0.1041368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_full    0.648
_reflns_Friedel_fraction_max     0.615
_reflns_number_gt                4651
_reflns_number_total             4672
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4672
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.050
_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)+(0.0471P)²+1.2039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C25(H25), C16(H16), C15(H15), C6(H6), C27(H27), C21(H21),
 C28(H28), C18(H18), C3(H3), C5(H5), C19(H19), C4(H4)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C2S(H2SA,H2SB,H2SC), C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1S S 0.45866(5) 0.07742(3) 0.29541(4) 0.02769(13) Uani 1 1 d . . . . .
O1 O 0.56649(14) 0.33827(9) 0.70829(11) 0.0202(3) Uani 1 1 d . . . . .
O4 O 0.44722(14) 0.09101(8) 0.60819(12) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.51079(14) 0.14998(9) 0.74639(11) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.25255(15) 0.36799(10) 0.70998(13) 0.0294(4) Uani 1 1 d . . . . .
N4 N 0.47426(15) 0.14968(10) 0.65837(13) 0.0193(3) Uani 1 1 d . . . . .
O1S O 0.4630(2) 0.13532(15) 0.37276(15) 0.0484(6) Uani 1 1 d . . . . .
N2 N 0.36500(16) 0.34129(10) 0.60746(13) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.34724(16) 0.31713(10) 0.50890(13) 0.0205(4) Uani 1 1 d . . . . .
N3 N 0.22884(16) 0.19280(10) 0.61853(13) 0.0203(4) Uani 1 1 d . . . . .
C9 C 0.2587(2) 0.35816(12) 0.62853(18) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.45858(18) 0.29499(11) 0.67085(15) 0.0180(4) Uani 1 1 d . . . . .
H11 H 0.4299 0.2754 0.7253 0.022 Uiso 1 1 calc R U . . .
C24 C 0.7726(2) 0.20697(13) 0.72188(16) 0.0220(4) Uani 1 1 d . . . . .
H24 H 0.7629 0.2579 0.7439 0.026 Uiso 1 1 calc R U . . .
C14 C 0.61603(18) 0.36418(12) 0.63707(15) 0.0184(4) Uani 1 1 d . . . . .
C20 C 0.7778(2) 0.31417(14) 0.37067(17) 0.0255(5) Uani 1 1 d . . . . .
H20 H 0.7947 0.2794 0.3253 0.031 Uiso 1 1 calc R U . . .
C23 C 0.69412(18) 0.18068(12) 0.63513(15) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.24230(19) 0.19338(12) 0.52953(15) 0.0193(4) Uani 1 1 d . . . . .
C22 C 0.68927(18) 0.33844(12) 0.50062(15) 0.0172(4) Uani 1 1 d . . . . .
C25 C 0.8646(2) 0.15982(14) 0.77659(17) 0.0250(5) Uani 1 1 d . . . . .
H25 H 0.9175 0.1790 0.8353 0.030 Uiso 1 1 calc R U . . .
C13 C 0.62929(18) 0.31301(11) 0.56871(15) 0.0162(4) Uani 1 1 d . . . . .
C1 C 0.35604(19) 0.23002(12) 0.51713(15) 0.0183(4) Uani 1 1 d . . . . .
H1 H 0.3739 0.2078 0.4591 0.022 Uiso 1 1 calc R U . . .
C26 C 0.8805(2) 0.08440(13) 0.74625(17) 0.0236(5) Uani 1 1 d . . . . .
C10 C 0.47062(18) 0.22559(11) 0.60549(14) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.7099(2) 0.46774(12) 0.57549(17) 0.0233(4) Uani 1 1 d . . . . .
H16 H 0.7351 0.5204 0.5772 0.028 Uiso 1 1 calc R U . . .
C15 C 0.65424(19) 0.44199(12) 0.64108(17) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.6416 0.4762 0.6886 0.026 Uiso 1 1 calc R U . . .
C17 C 0.73049(18) 0.41688(13) 0.50525(16) 0.0200(4) Uani 1 1 d . . . . .
C12 C 0.58965(17) 0.22928(11) 0.57326(15) 0.0164(4) Uani 1 1 d . . . . .
H12 H 0.5691 0.2080 0.5062 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1202(2) 0.17113(13) 0.62624(18) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.1097 0.1697 0.6888 0.029 Uiso 1 1 calc R U . . .
C27 C 0.8045(2) 0.05908(13) 0.65884(17) 0.0250(5) Uani 1 1 d . . . . .
H27 H 0.8156 0.0087 0.6361 0.030 Uiso 1 1 calc R U . . .
C21 C 0.71413(19) 0.28807(13) 0.43144(16) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.6866 0.2358 0.4269 0.025 Uiso 1 1 calc R U . . .
C29 C 0.9779(2) 0.03243(15) 0.80783(19) 0.0330(5) Uani 1 1 d . . . . .
H29A H 1.0576 0.0530 0.8095 0.050 Uiso 1 1 calc R U . . .
H29B H 0.9688 -0.0201 0.7805 0.050 Uiso 1 1 calc R U . . .
H29C H 0.9707 0.0306 0.8735 0.050 Uiso 1 1 calc R U . . .
C28 C 0.7123(2) 0.10627(12) 0.60384(16) 0.0220(4) Uani 1 1 d . . . . .
H28 H 0.6610 0.0876 0.5442 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2296(2) 0.35272(14) 0.45797(18) 0.0267(5) Uani 1 1 d . . . . .
H7A H 0.1830 0.3179 0.4059 0.032 Uiso 1 1 calc R U . . .
H7B H 0.2422 0.4029 0.4289 0.032 Uiso 1 1 calc R U . . .
C18 C 0.7949(2) 0.44198(14) 0.44039(18) 0.0248(4) Uani 1 1 d . . . . .
H18 H 0.8221 0.4942 0.4427 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1511(2) 0.16998(13) 0.44768(17) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.1654 0.1681 0.3865 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0231(2) 0.15089(14) 0.54889(19) 0.0294(5) Uani 1 1 d . . . . .
H5 H -0.0529 0.1382 0.5578 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8180(2) 0.39173(15) 0.37489(17) 0.0274(5) Uani 1 1 d . . . . .
H19 H 0.8612 0.4091 0.3322 0.033 Uiso 1 1 calc R U . . .
C2S C 0.4717(2) 0.13155(17) 0.1943(2) 0.0342(6) Uani 1 1 d . . . . .
H2SA H 0.3984 0.1626 0.1681 0.051 Uiso 1 1 calc R U . . .
H2SB H 0.4820 0.0958 0.1447 0.051 Uiso 1 1 calc R U . . .
H2SC H 0.5421 0.1661 0.2146 0.051 Uiso 1 1 calc R U . . .
C8 C 0.1608(2) 0.36545(14) 0.53287(18) 0.0268(5) Uani 1 1 d . . . . .
H8A H 0.1228 0.4176 0.5257 0.032 Uiso 1 1 calc R U . . .
H8B H 0.0973 0.3255 0.5267 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0391(2) 0.14953(14) 0.45750(18) 0.0283(5) Uani 1 1 d . . . . .
H4 H -0.0255 0.1349 0.4028 0.034 Uiso 1 1 calc R U . . .
C1S C 0.6056(3) 0.03346(15) 0.3273(2) 0.0358(6) Uani 1 1 d . . . . .
H1SA H 0.6677 0.0741 0.3391 0.054 Uiso 1 1 calc R U . . .
H1SB H 0.6125 0.0000 0.2745 0.054 Uiso 1 1 calc R U . . .
H1SC H 0.6171 0.0023 0.3859 0.054 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
S1S O1S 1.490(2) . ?
S1S C2S 1.780(3) . ?
S1S C1S 1.791(3) . ?
O1 C11 1.417(2) . ?
O1 C14 1.392(2) . ?
O4 N4 1.230(2) . ?
O3 N4 1.222(2) . ?
O2 C9 1.216(3) . ?
N4 C10 1.509(2) . ?
N2 N1 1.444(3) . ?
N2 C9 1.380(3) . ?
N2 C11 1.438(3) . ?
N1 C1 1.505(3) . ?
N1 C7 1.476(3) . ?
N3 C2 1.344(3) . ?
N3 C6 1.345(3) . ?
C9 C8 1.517(3) . ?
C11 H11 1.0000 . ?
C11 C10 1.556(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.394(3) . ?
C24 C25 1.388(3) . ?
C14 C13 1.367(3) . ?
C14 C15 1.406(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(3) . ?
C20 C19 1.409(3) . ?
C23 C12 1.526(3) . ?
C23 C28 1.395(3) . ?
C2 C1 1.515(3) . ?
C2 C3 1.397(3) . ?
C22 C13 1.430(3) . ?
C22 C17 1.426(3) . ?
C22 C21 1.417(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.399(3) . ?
C13 C12 1.519(3) . ?
C1 H1 1.0000 . ?
C1 C10 1.552(3) . ?
C26 C27 1.384(3) . ?
C26 C29 1.509(3) . ?
C10 C12 1.577(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.368(3) . ?
C16 C17 1.415(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.426(3) . ?
C12 H12 1.0000 . ?
C6 H6 0.9500 . ?
C6 C5 1.380(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C21 H21 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C28 H28 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.538(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.367(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.391(4) . ?
C19 H19 0.9500 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C4 H4 0.9500 . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 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
O1S S1S C2S 106.12(15) . . ?
O1S S1S C1S 105.48(13) . . ?
C2S S1S C1S 97.57(12) . . ?
C14 O1 C11 112.97(16) . . ?
O4 N4 C10 116.44(17) . . ?
O3 N4 O4 124.89(18) . . ?
O3 N4 C10 118.50(17) . . ?
C9 N2 N1 113.65(18) . . ?
C9 N2 C11 121.75(18) . . ?
C11 N2 N1 109.64(16) . . ?
N2 N1 C1 102.80(15) . . ?
N2 N1 C7 102.69(17) . . ?
C7 N1 C1 118.93(17) . . ?
C2 N3 C6 117.02(19) . . ?
O2 C9 N2 123.5(2) . . ?
O2 C9 C8 129.6(2) . . ?
N2 C9 C8 106.78(19) . . ?
O1 C11 N2 111.51(16) . . ?
O1 C11 H11 109.4 . . ?
O1 C11 C10 114.31(16) . . ?
N2 C11 H11 109.4 . . ?
N2 C11 C10 102.72(16) . . ?
C10 C11 H11 109.4 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C25 C24 C23 120.9(2) . . ?
O1 C14 C15 117.81(18) . . ?
C13 C14 O1 119.27(18) . . ?
C13 C14 C15 122.88(19) . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C19 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C24 C23 C12 123.15(18) . . ?
C24 C23 C28 118.1(2) . . ?
C28 C23 C12 118.70(19) . . ?
N3 C2 C1 117.69(18) . . ?
N3 C2 C3 122.9(2) . . ?
C3 C2 C1 118.97(19) . . ?
C17 C22 C13 118.65(18) . . ?
C21 C22 C13 122.73(18) . . ?
C21 C22 C17 118.57(18) . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.7(2) . . ?
C26 C25 H25 119.6 . . ?
C14 C13 C22 118.87(18) . . ?
C14 C13 C12 118.70(18) . . ?
C22 C13 C12 122.21(18) . . ?
N1 C1 C2 112.54(16) . . ?
N1 C1 H1 109.9 . . ?
N1 C1 C10 97.82(15) . . ?
C2 C1 H1 109.9 . . ?
C2 C1 C10 116.21(17) . . ?
C10 C1 H1 109.9 . . ?
C25 C26 C29 120.5(2) . . ?
C27 C26 C25 118.3(2) . . ?
C27 C26 C29 121.3(2) . . ?
N4 C10 C11 110.43(16) . . ?
N4 C10 C1 110.64(16) . . ?
N4 C10 C12 106.75(15) . . ?
C11 C10 C12 112.97(15) . . ?
C1 C10 C11 104.99(16) . . ?
C1 C10 C12 111.12(16) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.80(19) . . ?
C17 C16 H16 119.6 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C16 C17 C22 119.69(19) . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 C22 119.1(2) . . ?
C23 C12 C10 114.32(16) . . ?
C23 C12 H12 107.1 . . ?
C13 C12 C23 110.41(16) . . ?
C13 C12 C10 110.55(15) . . ?
C13 C12 H12 107.1 . . ?
C10 C12 H12 107.1 . . ?
N3 C6 H6 118.0 . . ?
N3 C6 C5 124.0(2) . . ?
C5 C6 H6 118.0 . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.0(2) . . ?
C28 C27 H27 119.5 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 119.6 . . ?
N1 C7 H7A 110.3 . . ?
N1 C7 H7B 110.3 . . ?
N1 C7 C8 107.21(18) . . ?
H7A C7 H7B 108.5 . . ?
C8 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.6 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.4(2) . . ?
C4 C5 H5 120.8 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
S1S C2S H2SA 109.5 . . ?
S1S C2S H2SB 109.5 . . ?
S1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C9 C8 C7 103.46(18) . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.0 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

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 C11 C10 N4 105.33(19) . . . . ?
O1 C11 C10 C1 -135.38(17) . . . . ?
O1 C11 C10 C12 -14.1(2) . . . . ?
O1 C14 C13 C22 -174.93(18) . . . . ?
O1 C14 C13 C12 -0.2(3) . . . . ?
O1 C14 C15 C16 176.1(2) . . . . ?
O4 N4 C10 C11 158.81(17) . . . . ?
O4 N4 C10 C1 43.0(2) . . . . ?
O4 N4 C10 C12 -78.0(2) . . . . ?
O3 N4 C10 C11 -25.9(2) . . . . ?
O3 N4 C10 C1 -141.67(17) . . . . ?
O3 N4 C10 C12 97.3(2) . . . . ?
O2 C9 C8 C7 175.1(2) . . . . ?
N4 C10 C12 C23 -24.9(2) . . . . ?
N4 C10 C12 C13 -150.18(16) . . . . ?
N2 N1 C1 C2 76.8(2) . . . . ?
N2 N1 C1 C10 -45.82(17) . . . . ?
N2 N1 C7 C8 -24.0(2) . . . . ?
N2 C9 C8 C7 -1.7(2) . . . . ?
N2 C11 C10 N4 -133.72(16) . . . . ?
N2 C11 C10 C1 -14.43(19) . . . . ?
N2 C11 C10 C12 106.81(18) . . . . ?
N1 N2 C9 O2 168.48(19) . . . . ?
N1 N2 C9 C8 -14.5(2) . . . . ?
N1 N2 C11 O1 107.40(18) . . . . ?
N1 N2 C11 C10 -15.5(2) . . . . ?
N1 C1 C10 N4 155.83(15) . . . . ?
N1 C1 C10 C11 36.68(18) . . . . ?
N1 C1 C10 C12 -85.77(17) . . . . ?
N1 C7 C8 C9 16.3(2) . . . . ?
N3 C2 C1 N1 -81.7(2) . . . . ?
N3 C2 C1 C10 30.0(3) . . . . ?
N3 C2 C3 C4 3.9(3) . . . . ?
N3 C6 C5 C4 2.8(4) . . . . ?
C9 N2 N1 C1 -99.47(19) . . . . ?
C9 N2 N1 C7 24.6(2) . . . . ?
C9 N2 C11 O1 -116.4(2) . . . . ?
C9 N2 C11 C10 120.7(2) . . . . ?
C11 O1 C14 C13 -48.3(3) . . . . ?
C11 O1 C14 C15 133.92(19) . . . . ?
C11 N2 N1 C1 40.56(19) . . . . ?
C11 N2 N1 C7 164.58(16) . . . . ?
C11 N2 C9 O2 33.8(3) . . . . ?
C11 N2 C9 C8 -149.11(19) . . . . ?
C11 C10 C12 C23 96.7(2) . . . . ?
C11 C10 C12 C13 -28.6(2) . . . . ?
C24 C23 C12 C13 41.9(3) . . . . ?
C24 C23 C12 C10 -83.5(2) . . . . ?
C24 C23 C28 C27 1.4(3) . . . . ?
C24 C25 C26 C27 2.1(3) . . . . ?
C24 C25 C26 C29 -177.8(2) . . . . ?
C14 O1 C11 N2 -62.2(2) . . . . ?
C14 O1 C11 C10 53.8(2) . . . . ?
C14 C13 C12 C23 -89.7(2) . . . . ?
C14 C13 C12 C10 37.8(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C2 N3 C6 C5 -0.9(3) . . . . ?
C2 C1 C10 N4 35.9(2) . . . . ?
C2 C1 C10 C11 -83.2(2) . . . . ?
C2 C1 C10 C12 154.31(17) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C22 C13 C12 C23 84.8(2) . . . . ?
C22 C13 C12 C10 -147.69(19) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C25 C24 C23 C12 178.55(19) . . . . ?
C25 C24 C23 C28 -1.3(3) . . . . ?
C25 C26 C27 C28 -2.1(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C13 C22 C17 C16 -0.9(3) . . . . ?
C13 C22 C17 C18 177.4(2) . . . . ?
C13 C22 C21 C20 -176.6(2) . . . . ?
C1 N1 C7 C8 88.6(2) . . . . ?
C1 C2 C3 C4 -168.6(2) . . . . ?
C1 C10 C12 C23 -145.59(17) . . . . ?
C1 C10 C12 C13 89.1(2) . . . . ?
C26 C27 C28 C23 0.3(3) . . . . ?
C16 C17 C18 C19 177.7(2) . . . . ?
C15 C14 C13 C22 2.8(3) . . . . ?
C15 C14 C13 C12 177.50(19) . . . . ?
C15 C16 C17 C22 2.0(3) . . . . ?
C15 C16 C17 C18 -176.2(2) . . . . ?
C17 C22 C13 C14 -1.4(3) . . . . ?
C17 C22 C13 C12 -175.98(18) . . . . ?
C17 C22 C21 C20 0.6(3) . . . . ?
C17 C16 C15 C14 -0.8(3) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C12 C23 C28 C27 -178.50(19) . . . . ?
C6 N3 C2 C1 170.11(19) . . . . ?
C6 N3 C2 C3 -2.5(3) . . . . ?
C6 C5 C4 C3 -1.2(4) . . . . ?
C21 C20 C19 C18 0.5(4) . . . . ?
C21 C22 C13 C14 175.7(2) . . . . ?
C21 C22 C13 C12 1.2(3) . . . . ?
C21 C22 C17 C16 -178.2(2) . . . . ?
C21 C22 C17 C18 0.1(3) . . . . ?
C29 C26 C27 C28 177.9(2) . . . . ?
C28 C23 C12 C13 -138.25(19) . . . . ?
C28 C23 C12 C10 96.4(2) . . . . ?
C7 N1 C1 C2 -35.7(3) . . . . ?
C7 N1 C1 C10 -158.33(17) . . . . ?
C3 C2 C1 N1 91.2(2) . . . . ?
C3 C2 C1 C10 -157.15(19) . . . . ?
C19 C20 C21 C22 -0.9(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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.723

####################################################################### 
# 
# 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_kor_20_autored
_database_code_depnum_ccdc_archive 'CCDC 2117341'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;

_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(7aR*,13R*,13aS*)-13a-Amino-13-(2-bromophenyl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one '
_chemical_name_common            
'(7aR*,13R*,13aS*)-13a-Amino-13-(2-bromophenyl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one '
_chemical_formula_moiety         'C23 H20 Br N3 O2'
_chemical_formula_sum            'C23 H20 Br N3 O2'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         450.33
_exptl_crystal_recrystallization_method 'from MeCN'
_chemical_melting_point          493-495
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100.01(10)
_chemical_oxdiff_formula         'C23 H20 Br N3 O2'
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'
Br Br -0.6763 1.2805 '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                   22.22011(17)
_cell_length_b                   7.84209(3)
_cell_length_c                   24.48716(18)
_cell_angle_alpha                90
_cell_angle_beta                 116.6327(9)
_cell_angle_gamma                90
_cell_volume                     3814.21(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15958
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.7780
_cell_measurement_theta_min      2.2270
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.312
_exptl_absorpt_coefficient_mu    3.148
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 0 -3 0.0699
11 0 3 0.0692
-8 0 -8 0.0799
0 0 -14 0.1016
3 5 3 0.2147
9 0 -16 0.1105
-5 -5 1 0.2143
-3 -5 -2 0.2147
14 0 -10 0.0991
-13 0 2 0.0572
13 0 -1 0.0577
2 -5 -1 0.2260
0 0 -14 0.0880
0 0 14 0.0885
5 0 -16 0.1013
-5 0 16 0.1021
-3 0 15 0.0830

_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.121
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
-11.2527 -0.1622 -3.3196 0.3981 0.8384 0.3723
11.2782 0.0334 3.2868 -0.4020 -0.8467 -0.3486
-8.1610 0.2718 -7.6598 0.1230 0.9459 0.3004
-0.2845 -0.3653 -14.0285 -0.4490 0.8235 0.3467
3.1089 4.7544 2.5075 0.0062 -0.0070 -1.0000
8.7437 0.1496 -15.6131 -0.9014 0.4288 0.0598
-4.9554 -4.7518 0.9930 0.1913 -0.0933 0.9771
-3.0156 -4.7741 -2.4395 -0.0085 -0.0038 1.0000
13.9835 0.3956 -10.2198 -0.9592 -0.1782 -0.2196
-13.4658 0.1490 1.5743 0.6617 0.6977 0.2746
13.4412 0.0098 -1.4823 -0.6554 -0.6910 -0.3050
2.0040 -5.0401 -0.9219 -0.1895 -0.4029 0.8954
0.0397 0.1573 -14.2215 -0.4628 0.8516 0.2463
0.0290 -0.0540 14.1936 0.4602 -0.8469 -0.2665
4.7252 0.3646 -15.7208 -0.7205 0.6828 0.1216
-4.5084 -0.0956 15.7216 0.7144 -0.6772 -0.1765
-2.6971 0.2914 15.2667 0.6230 -0.7290 -0.2835

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.086
_diffrn_reflns_theta_min         4.039
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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 -16.00   1.00    1.00    --  -40.82 -38.00 120.00   99
  2  ω    -65.00  33.00   1.00    1.00    --  -40.82  38.00  90.00   98
  3  ω    -21.00  73.00   1.00    1.00    --   40.82 -77.00 -90.00   94
  4  ω    103.00 178.00   1.00    1.11    --  112.00  77.00  90.00   75
  5  ω     59.00 178.00   1.00    1.11    --  112.00  15.00 -90.00  119
  6  ω     36.00 140.00   1.00    1.11    --  112.00 -30.00   0.00  104
  7  ω    104.00 178.00   1.00    1.11    --  112.00 111.00  30.00   74
  8  ω     86.00 178.00   1.00    1.11    --  112.00  45.00-120.00   92
  9  ω     30.00 106.00   1.00    1.11    --  112.00 -95.00 -60.00   76
 10  ω     86.00 178.00   1.00    1.11    --  112.00  45.00-180.00   92
 11  ω     30.00 106.00   1.00    1.11    --  112.00 -95.00   0.00   76
 12  ω     30.00 106.00   1.00    1.11    --  112.00 -95.00 -90.00   76
 13  ω     30.00 106.00   1.00    1.11    --  112.00 -95.00 -30.00   76
 14  ω     36.00 109.00   1.00    1.11    --  112.00-111.00   0.00   73
 15  ω     39.00 138.00   1.00    1.11    --  112.00 -45.00   0.00   99
 16  ω     40.00 141.00   1.00    1.11    --  112.00 -61.00-180.00  101
 17  ω     30.00 106.00   1.00    1.11    --  112.00 -95.00 150.00   76
 18  ω     36.00 109.00   1.00    1.11    --  112.00-111.00 -30.00   73
 19  ω     52.00 139.00   1.00    1.11    --  112.00 -61.00-120.00   87
 20  ω    101.00 131.00   1.00    1.11    --  112.00 -77.00-180.00   30
 21  ω     25.00 129.00   1.00    1.11    --  112.00   0.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0451783000
_diffrn_orient_matrix_UB_12      0.0136700000
_diffrn_orient_matrix_UB_13      0.0325659000
_diffrn_orient_matrix_UB_21      -0.0579939000
_diffrn_orient_matrix_UB_22      0.0677312000
_diffrn_orient_matrix_UB_23      -0.0592908000
_diffrn_orient_matrix_UB_31      -0.0247015000
_diffrn_orient_matrix_UB_32      -0.1839266000
_diffrn_orient_matrix_UB_33      -0.0194250000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3912
_reflns_number_total             3971
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.00112(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   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+6.3937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C17(H17A,H17B), C3(H3C,H3D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C19(H19), C9(H9), C22(H22), C14(H14), C21(H21), C13(H13), C20(H20),
 C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.49081(2) 0.29383(2) 0.73752(2) 0.01879(8) Uani 1 1 d . . . . .
O1 O 0.63809(6) 0.63802(13) 0.68293(5) 0.0141(2) Uani 1 1 d . . . . .
O2 O 0.60185(5) 0.91550(14) 0.57728(5) 0.0153(2) Uani 1 1 d . . . . .
N2 N 0.48875(6) 0.60437(15) 0.57891(6) 0.0101(2) Uani 1 1 d . . . . .
N1 N 0.55379(6) 0.66279(16) 0.58434(6) 0.0105(2) Uani 1 1 d . . . . .
N3 N 0.55106(7) 0.29668(16) 0.56678(6) 0.0115(3) Uani 1 1 d . . . . .
C16 C 0.65605(7) 0.36541(19) 0.73520(6) 0.0110(3) Uani 1 1 d . . . . .
C7 C 0.66876(7) 0.53668(19) 0.73389(6) 0.0114(3) Uani 1 1 d . . . . .
C4 C 0.48559(7) 0.90255(18) 0.56527(7) 0.0120(3) Uani 1 1 d . . . . .
H4A H 0.456463 0.921455 0.521181 0.014 Uiso 1 1 calc R U . . .
H4B H 0.489552 1.010494 0.587602 0.014 Uiso 1 1 calc R U . . .
C5 C 0.55440(8) 0.83605(19) 0.57645(6) 0.0112(3) Uani 1 1 d . . . . .
C1 C 0.57033(7) 0.38939(18) 0.62357(6) 0.0102(3) Uani 1 1 d . . . . .
C18 C 0.44849(7) 0.34479(19) 0.60853(7) 0.0107(3) Uani 1 1 d . . . . .
C8 C 0.71443(7) 0.62658(19) 0.78638(7) 0.0128(3) Uani 1 1 d . . . . .
H8 H 0.722133 0.744739 0.783678 0.015 Uiso 1 1 calc R U . . .
C19 C 0.40355(8) 0.31467(19) 0.54730(7) 0.0131(3) Uani 1 1 d . . . . .
H19 H 0.408230 0.377574 0.516270 0.016 Uiso 1 1 calc R U . . .
C2 C 0.50626(7) 0.46783(17) 0.62492(6) 0.0097(3) Uani 1 1 d . . . . .
H2 H 0.518511 0.518759 0.666000 0.012 Uiso 1 1 calc R U . . .
C17 C 0.61100(8) 0.27174(18) 0.67726(7) 0.0117(3) Uani 1 1 d . . . . .
H17A H 0.579497 0.198925 0.685370 0.014 Uiso 1 1 calc R U . . .
H17B H 0.639087 0.195974 0.665735 0.014 Uiso 1 1 calc R U . . .
C9 C 0.74723(7) 0.5436(2) 0.84062(7) 0.0137(3) Uani 1 1 d . . . . .
H9 H 0.778649 0.603633 0.875445 0.016 Uiso 1 1 calc R U . . .
C22 C 0.38894(8) 0.12698(19) 0.63679(7) 0.0151(3) Uani 1 1 d . . . . .
H22 H 0.384744 0.061797 0.667608 0.018 Uiso 1 1 calc R U . . .
C6 C 0.60806(7) 0.55553(18) 0.62446(6) 0.0107(3) Uani 1 1 d . . . . .
H6 H 0.641714 0.536441 0.608391 0.013 Uiso 1 1 calc R U . . .
C14 C 0.67593(8) 0.1033(2) 0.79962(7) 0.0158(3) Uani 1 1 d . . . . .
H14 H 0.646331 0.039765 0.764901 0.019 Uiso 1 1 calc R U . . .
C10 C 0.73485(7) 0.3678(2) 0.84559(7) 0.0129(3) Uani 1 1 d . . . . .
C23 C 0.43855(8) 0.2510(2) 0.65242(7) 0.0128(3) Uani 1 1 d . . . . .
C21 C 0.34556(8) 0.0995(2) 0.57557(8) 0.0169(3) Uani 1 1 d . . . . .
H21 H 0.311292 0.015357 0.564284 0.020 Uiso 1 1 calc R U . . .
C3 C 0.45811(8) 0.75971(19) 0.59002(7) 0.0140(3) Uani 1 1 d . . . . .
H3C H 0.471934 0.775306 0.634165 0.017 Uiso 1 1 calc R U . . .
H3D H 0.408362 0.754668 0.567896 0.017 Uiso 1 1 calc R U . . .
C15 C 0.68878(7) 0.27797(19) 0.79266(7) 0.0119(3) Uani 1 1 d . . . . .
C13 C 0.70582(9) 0.0253(2) 0.85600(7) 0.0191(3) Uani 1 1 d . . . . .
H13 H 0.695499 -0.090233 0.859894 0.023 Uiso 1 1 calc R U . . .
C20 C 0.35226(8) 0.1950(2) 0.53082(7) 0.0163(3) Uani 1 1 d . . . . .
H20 H 0.321810 0.178426 0.488987 0.020 Uiso 1 1 calc R U . . .
C11 C 0.76623(8) 0.2824(2) 0.90258(7) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.797837 0.341704 0.937504 0.020 Uiso 1 1 calc R U . . .
C12 C 0.75151(9) 0.1150(2) 0.90792(7) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.772081 0.059880 0.946533 0.023 Uiso 1 1 calc R U . . .
H3A H 0.5425(11) 0.361(3) 0.5394(11) 0.022(5) Uiso 1 1 d . . . . .
H3B H 0.5821(12) 0.229(3) 0.5705(10) 0.020(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
Br1 C23 1.9065(15) . ?
O1 C7 1.3751(17) . ?
O1 C6 1.4343(17) . ?
O2 C5 1.2169(19) . ?
N2 N1 1.4641(16) . ?
N2 C2 1.4745(18) . ?
N2 C3 1.4791(19) . ?
N1 C5 1.3733(19) . ?
N1 C6 1.4370(18) . ?
N3 C1 1.4533(18) . ?
N3 H3A 0.79(3) . ?
N3 H3B 0.84(2) . ?
C16 C7 1.376(2) . ?
C16 C17 1.510(2) . ?
C16 C15 1.436(2) . ?
C7 C8 1.418(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(2) . ?
C4 C3 1.525(2) . ?
C1 C2 1.565(2) . ?
C1 C17 1.5268(19) . ?
C1 C6 1.5442(19) . ?
C18 C19 1.399(2) . ?
C18 C2 1.509(2) . ?
C18 C23 1.399(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.360(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C2 H2 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.421(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C22 C21 1.388(2) . ?
C6 H6 1.0000 . ?
C14 H14 0.9500 . ?
C14 C15 1.425(2) . ?
C14 C13 1.378(2) . ?
C10 C15 1.426(2) . ?
C10 C11 1.418(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.389(2) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.409(2) . ?
C20 H20 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C6 117.70(11) . . ?
N1 N2 C2 104.25(10) . . ?
N1 N2 C3 104.04(11) . . ?
C2 N2 C3 116.29(12) . . ?
C5 N1 N2 111.63(12) . . ?
C5 N1 C6 128.10(12) . . ?
C6 N1 N2 111.76(11) . . ?
C1 N3 H3A 110.2(17) . . ?
C1 N3 H3B 109.6(16) . . ?
H3A N3 H3B 112(2) . . ?
C7 C16 C17 120.62(13) . . ?
C7 C16 C15 118.03(14) . . ?
C15 C16 C17 121.30(13) . . ?
O1 C7 C16 124.19(13) . . ?
O1 C7 C8 113.42(13) . . ?
C16 C7 C8 122.37(14) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C5 C4 C3 103.07(12) . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
O2 C5 N1 124.57(14) . . ?
O2 C5 C4 128.42(14) . . ?
N1 C5 C4 106.99(12) . . ?
N3 C1 C2 109.65(12) . . ?
N3 C1 C17 109.18(12) . . ?
N3 C1 C6 111.15(12) . . ?
C17 C1 C2 114.34(12) . . ?
C17 C1 C6 112.94(12) . . ?
C6 C1 C2 99.29(11) . . ?
C19 C18 C2 120.40(13) . . ?
C23 C18 C19 116.85(14) . . ?
C23 C18 C2 122.70(13) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.99(14) . . ?
C9 C8 H8 120.0 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.58(14) . . ?
C20 C19 H19 119.2 . . ?
N2 C2 C1 101.55(11) . . ?
N2 C2 C18 111.07(11) . . ?
N2 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C18 C2 C1 114.61(12) . . ?
C18 C2 H2 109.8 . . ?
C16 C17 C1 113.72(12) . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C1 C17 H17A 108.8 . . ?
C1 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.52(14) . . ?
C10 C9 H9 119.7 . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.18(14) . . ?
O1 C6 N1 106.90(11) . . ?
O1 C6 C1 113.66(11) . . ?
O1 C6 H6 111.4 . . ?
N1 C6 C1 101.55(11) . . ?
N1 C6 H6 111.4 . . ?
C1 C6 H6 111.4 . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.94(15) . . ?
C9 C10 C15 119.27(14) . . ?
C11 C10 C9 120.93(14) . . ?
C11 C10 C15 119.79(14) . . ?
C18 C23 Br1 121.21(12) . . ?
C22 C23 Br1 116.36(11) . . ?
C22 C23 C18 122.38(14) . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 119.99(15) . . ?
C20 C21 H21 120.0 . . ?
N2 C3 C4 103.44(12) . . ?
N2 C3 H3C 111.1 . . ?
N2 C3 H3D 111.1 . . ?
C4 C3 H3C 111.1 . . ?
C4 C3 H3D 111.1 . . ?
H3C C3 H3D 109.0 . . ?
C14 C15 C16 122.39(14) . . ?
C14 C15 C10 117.84(14) . . ?
C10 C15 C16 119.76(14) . . ?
C14 C13 H13 119.6 . . ?
C14 C13 C12 120.73(15) . . ?
C12 C13 H13 119.6 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.93(15) . . ?
C21 C20 H20 120.0 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.83(15) . . ?
C12 C11 H11 119.6 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.83(15) . . ?
C11 C12 H12 120.1 . . ?

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 C7 C8 C9 178.31(13) . . . . ?
N2 N1 C5 O2 -178.12(13) . . . . ?
N2 N1 C5 C4 0.44(15) . . . . ?
N2 N1 C6 O1 -97.93(13) . . . . ?
N2 N1 C6 C1 21.42(14) . . . . ?
N1 N2 C2 C1 -33.19(13) . . . . ?
N1 N2 C2 C18 -155.49(11) . . . . ?
N1 N2 C3 C4 31.48(14) . . . . ?
N3 C1 C2 N2 -71.10(13) . . . . ?
N3 C1 C2 C18 48.71(16) . . . . ?
N3 C1 C17 C16 157.16(12) . . . . ?
N3 C1 C6 O1 -170.20(12) . . . . ?
N3 C1 C6 N1 75.38(14) . . . . ?
C16 C7 C8 C9 -0.4(2) . . . . ?
C7 O1 C6 N1 151.75(12) . . . . ?
C7 O1 C6 C1 40.55(17) . . . . ?
C7 C16 C17 C1 -13.4(2) . . . . ?
C7 C16 C15 C14 176.16(14) . . . . ?
C7 C16 C15 C10 -2.3(2) . . . . ?
C7 C8 C9 C10 -1.6(2) . . . . ?
C5 N1 C6 O1 46.89(19) . . . . ?
C5 N1 C6 C1 166.23(14) . . . . ?
C5 C4 C3 N2 -31.13(14) . . . . ?
C18 C19 C20 C21 -1.3(2) . . . . ?
C8 C9 C10 C15 1.5(2) . . . . ?
C8 C9 C10 C11 -176.81(14) . . . . ?
C19 C18 C2 N2 30.28(19) . . . . ?
C19 C18 C2 C1 -84.08(17) . . . . ?
C19 C18 C23 Br1 -174.26(11) . . . . ?
C19 C18 C23 C22 3.3(2) . . . . ?
C2 N2 N1 C5 -142.98(12) . . . . ?
C2 N2 N1 C6 7.83(14) . . . . ?
C2 N2 C3 C4 145.47(12) . . . . ?
C2 C1 C17 C16 -79.60(16) . . . . ?
C2 C1 C6 O1 74.42(13) . . . . ?
C2 C1 C6 N1 -40.00(13) . . . . ?
C2 C18 C19 C20 176.28(14) . . . . ?
C2 C18 C23 Br1 8.4(2) . . . . ?
C2 C18 C23 C22 -174.12(14) . . . . ?
C17 C16 C7 O1 6.0(2) . . . . ?
C17 C16 C7 C8 -175.42(14) . . . . ?
C17 C16 C15 C14 -6.1(2) . . . . ?
C17 C16 C15 C10 175.39(13) . . . . ?
C17 C1 C2 N2 165.92(11) . . . . ?
C17 C1 C2 C18 -74.27(15) . . . . ?
C17 C1 C6 O1 -47.09(17) . . . . ?
C17 C1 C6 N1 -161.51(12) . . . . ?
C9 C10 C15 C16 0.5(2) . . . . ?
C9 C10 C15 C14 -178.08(14) . . . . ?
C9 C10 C11 C12 176.55(15) . . . . ?
C22 C21 C20 C19 1.8(2) . . . . ?
C6 O1 C7 C16 -20.3(2) . . . . ?
C6 O1 C7 C8 161.00(13) . . . . ?
C6 N1 C5 O2 37.0(2) . . . . ?
C6 N1 C5 C4 -144.41(14) . . . . ?
C6 C1 C2 N2 45.43(12) . . . . ?
C6 C1 C2 C18 165.24(11) . . . . ?
C6 C1 C17 C16 32.97(17) . . . . ?
C14 C13 C12 C11 0.4(3) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C23 C18 C19 C20 -1.2(2) . . . . ?
C23 C18 C2 N2 -152.44(14) . . . . ?
C23 C18 C2 C1 93.21(16) . . . . ?
C23 C22 C21 C20 0.3(2) . . . . ?
C21 C22 C23 Br1 174.78(12) . . . . ?
C21 C22 C23 C18 -2.9(2) . . . . ?
C3 N2 N1 C5 -20.66(15) . . . . ?
C3 N2 N1 C6 130.14(12) . . . . ?
C3 N2 C2 C1 -147.06(12) . . . . ?
C3 N2 C2 C18 90.65(15) . . . . ?
C3 C4 C5 O2 -162.28(15) . . . . ?
C3 C4 C5 N1 19.24(15) . . . . ?
C15 C16 C7 O1 -176.21(13) . . . . ?
C15 C16 C7 C8 2.3(2) . . . . ?
C15 C16 C17 C1 168.95(13) . . . . ?
C15 C14 C13 C12 -2.0(3) . . . . ?
C15 C10 C11 C12 -1.8(2) . . . . ?
C13 C14 C15 C16 -176.95(15) . . . . ?
C13 C14 C15 C10 1.6(2) . . . . ?
C11 C10 C15 C16 178.82(14) . . . . ?
C11 C10 C15 C14 0.3(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 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.711
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'I 2/a'
_symmetry_int_tables_number      15
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kor_12_300
_database_code_depnum_ccdc_archive 'CCDC 2083589'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-05-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'methyl 3-(5-(2-chlorophenyl)-4-(2,5-dihydroxyphenyl)-1H-pyrazol-1-yl)propanoate'
_chemical_name_common            
'methyl 3-(5-(2-chlorophenyl)-4-(2,5-dihydroxyphenyl)-1H-pyrazol-1-yl)propanoate'
_chemical_formula_moiety         'C19 H17 Cl N2 O4'
_chemical_formula_sum            'C19 H17 Cl N2 O4'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         372.79
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_melting_point          481-483
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_oxdiff_formula         'C19 H17 Cl N2 O4'
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'
Cl Cl 0.3639 0.7018 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.63400(10)
_cell_length_b                   13.47330(10)
_cell_length_c                   15.5128(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.0160(10)
_cell_angle_gamma                90
_cell_volume                     1803.46(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1530
_cell_measurement_theta_min      3.2600
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -8 0.1121
2 6 6 0.1330
-1 3 10 0.0841
0 -1 -10 0.0780
-2 6 -6 0.0855
-4 2 7 0.1144
-2 -2 9 0.1080
4 -2 -7 0.1282
5 -1 -5 0.1482
-5 1 5 0.1216
5 3 -1 0.1805
0 7 5 0.0927
0 7 -6 0.0728
-5 -3 1 0.1558
2 -6 6 0.0703
0 5 -8 0.0756
-5 -1 -4 0.1445
-2 -6 -6 0.1216
-1 -5 -8 0.0922
0 4 -9 0.0749

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.157
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
1.1255 -5.2503 -7.8620 0.1296 0.9915 -0.0091
2.2047 5.9247 6.1115 0.4780 -0.8783 -0.0092
-0.5340 2.8468 9.5017 -0.1233 -0.9377 -0.3248
0.0113 -0.6662 -10.0359 0.1079 0.8160 0.5678
-1.6004 6.4014 -6.1226 0.0011 -0.0093 1.0000
-3.8239 1.8231 7.2985 -0.6849 -0.7228 -0.0921
-2.0426 -2.2136 9.1506 -0.5293 -0.5567 -0.6402
3.7517 -1.5879 -7.4915 0.6823 0.7199 0.1275
4.8899 -0.5418 -5.1940 0.8783 0.4780 0.0090
-4.8899 0.5418 5.1940 -0.8783 -0.4780 -0.0090
5.2405 3.0892 -0.6537 0.9915 -0.1296 0.0090
0.1384 7.3139 5.4998 0.1776 -0.9497 0.2578
-0.2276 6.9179 -6.1274 0.2498 -0.0348 0.9677
-5.2405 -3.0892 0.6537 -0.9915 0.1296 -0.0090
1.6501 -6.3153 6.1936 0.0091 -0.0019 -1.0000
0.2223 4.7623 -8.4459 0.2895 0.3027 0.9081
-4.8881 -1.2412 -4.3999 -0.8117 0.3852 0.4391
-2.1756 -6.0404 -5.9986 -0.4780 0.8783 -0.0091
-0.7806 -4.9629 -8.1160 -0.1818 0.9740 0.1353
-0.3940 4.2410 -8.7480 0.1728 0.3583 0.9175

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20601
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.492
_diffrn_reflns_theta_min         4.348
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    1.00    --  -41.72 125.00 -30.00   81
  2  ω      9.00  42.00   1.00    1.00    --   41.72  80.00 116.20   33
  3  ω      8.00  42.00   1.00    1.00    --   41.72  81.00  54.29   34
  4  ω     27.00  98.00   1.00    1.00    --   41.72-125.00   0.00   71
  5  ω      7.00  33.00   1.00    1.00    --   41.72  84.00-150.01   26
  6  ω     14.00 115.00   1.00    1.00    --   41.72  57.00   0.00  101
  7  ω      7.00  33.00   1.00    1.00    --   41.72  84.00  32.09   26
  8  ω      9.00  42.00   1.00    1.00    --   41.72  77.00 173.91   33
  9  ω     32.00 153.00   1.00    3.07    --  112.00 -19.00  64.61  121
 10  ω     36.00 109.00   1.00    3.07    --  112.00-111.00  30.00   73
 11  ω     37.00 137.00   1.00    3.07    --  112.00 -34.00   7.04  100
 12  ω     36.00 109.00   1.00    3.07    --  112.00-111.00 -60.00   73
 13  ω     40.00 141.00   1.00    3.07    --  112.00 -62.00 -95.33  101
 14  ω     38.00 137.00   1.00    3.07    --  112.00 -42.00-102.71   99
 15  ω     30.00 165.00   1.00    3.07    --  112.00 -15.00-150.00  135
 16  ω    103.00 178.00   1.00    3.07    --  112.00  77.00 120.00   75
 17  ω     25.00 178.00   1.00    3.07    --  112.00  -2.00 126.08  153
 18  ω     70.00 139.00   1.00    3.07    --  112.00 -30.00-120.00   69
 19  ω     37.00  66.00   1.00    3.07    --  112.00 -30.00-120.00   29
 20  ω     44.00  88.00   1.00    3.07    --  112.00 -61.00 150.00   44
 21  ω     84.00 109.00   1.00    3.07    --  112.00-111.00 120.00   25
 22  ω    104.00 137.00   1.00    3.07    --  112.00 -45.00 -90.00   33
 23  ω     31.00  63.00   1.00    3.07    --  112.00 -15.00-150.00   32
 24  ω     60.00 128.00   1.00    3.07    --  112.00 -61.00  60.00   68
 25  ω    131.00 158.00   1.00    3.07    --  112.00  30.00-150.00   27
 26  ω     86.00 137.00   1.00    3.07    --  112.00 -45.00 150.00   51
 27  ω     78.00 128.00   1.00    3.07    --  112.00 -15.00 -30.00   50
 28  ω      8.00  33.00   1.00    1.00    --  -41.60  38.00  30.00   25
 29  ω     51.00  77.00   1.00    3.07    --  112.00 -95.00-120.00   26
 30  ω     68.00  94.00   1.00    3.07    --  112.00 -45.00  90.00   26
 31  ω    121.00 147.00   1.00    3.07    --  112.00  77.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1696322000
_diffrn_orient_matrix_UB_12      0.0305362000
_diffrn_orient_matrix_UB_13      -0.0125917000
_diffrn_orient_matrix_UB_21      0.0084655000
_diffrn_orient_matrix_UB_22      -0.0724976000
_diffrn_orient_matrix_UB_23      -0.0764902000
_diffrn_orient_matrix_UB_31      -0.0549707000
_diffrn_orient_matrix_UB_32      0.0830214000
_diffrn_orient_matrix_UB_33      -0.0621516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3646
_reflns_number_total             3783
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+2.1480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1612
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Rigid body (RIGU) restrains
 C18, C19, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14', C19', C18', C17', C16', C15'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C15)=Sof(C18')=Sof(H18')=Sof(C17')=Sof(H17')=Sof(C16')=Sof(H16')=Sof(C19)=
 Sof(H19)=Sof(Cl1')=1-FVAR(1)
 Sof(Cl1)=Sof(C15')=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=Sof(C19')=Sof(H19')=
 Sof(C18)=Sof(H18)=FVAR(1)
 Sof(C14)=1-FVAR(2)
 Sof(C14')=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1A), C7(H7), C6(H6), C17(H17), C16(H16), C19'(H19'), C18(H18),
 C18'(H18'), C17'(H17'), C16'(H16'), C19(H19)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1468(2) 0.47173(14) 0.21792(18) 0.0609(6) Uani 1 1 d . . . . .
H1 H 1.0631 0.4433 0.2123 0.091 Uiso 1 1 calc R U . . .
Cl1 Cl 0.9320(3) 0.7333(2) 0.51309(15) 0.0918(9) Uani 0.496(3) 1 d . . P A 1
O2 O 1.0694(3) 0.87377(15) 0.2668(2) 0.0795(9) Uani 1 1 d . . . . .
H2 H 1.1530 0.9021 0.2634 0.119 Uiso 1 1 calc R U . . .
N1 N 0.5975(3) 0.77776(16) 0.36221(17) 0.0478(6) Uani 1 1 d . . . . .
N2 N 0.5985(3) 0.84620(16) 0.29883(18) 0.0499(6) Uani 1 1 d . . . . .
C4 C 0.9639(3) 0.71140(17) 0.26764(17) 0.0350(5) Uani 1 1 d . . . . .
O4 O 0.2820(3) 0.9467(2) 0.55687(19) 0.0802(8) Uani 1 1 d . . . . .
C2 C 0.8145(3) 0.75206(17) 0.29528(18) 0.0378(5) Uani 1 1 d . . . . .
C9 C 0.9840(3) 0.60984(18) 0.25571(18) 0.0379(5) Uani 1 1 d . . . . .
H9 H 0.9026 0.5668 0.2663 0.046 Uiso 1 1 calc R U . . .
C8 C 1.1226(3) 0.57174(18) 0.22841(18) 0.0384(6) Uani 1 1 d . . . . .
C5 C 1.0885(3) 0.77430(18) 0.2525(2) 0.0445(6) Uani 1 1 d . . . . .
C1 C 0.7301(3) 0.83041(19) 0.2590(2) 0.0468(7) Uani 1 1 d . . . . .
H1A H 0.7620 0.8675 0.2122 0.056 Uiso 1 1 calc R U . . .
C7 C 1.2437(3) 0.6350(2) 0.2121(2) 0.0447(6) Uani 1 1 d . . . . .
H7 H 1.3369 0.6098 0.1932 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7263(3) 0.7197(2) 0.36200(19) 0.0451(6) Uani 1 1 d . . . . .
O3 O 0.2608(4) 0.7844(2) 0.5544(3) 0.1151(14) Uani 1 1 d . . . . .
C10 C 0.4689(3) 0.7741(2) 0.4205(2) 0.0514(7) Uani 1 1 d . . . . .
H10A H 0.4742 0.7124 0.4526 0.062 Uiso 1 1 calc R U . . .
H10B H 0.3722 0.7744 0.3867 0.062 Uiso 1 1 calc R U . . .
C6 C 1.2261(3) 0.7355(2) 0.2239(2) 0.0500(7) Uani 1 1 d . . . . .
H6 H 1.3077 0.7780 0.2124 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3255(4) 0.8576(3) 0.5339(2) 0.0644(9) Uani 1 1 d . . . . .
C14' C 0.7701(18) 0.6518(13) 0.4349(8) 0.045(3) Uani 0.50(4) 1 d . U P A 2
C11 C 0.4684(4) 0.8591(3) 0.4827(3) 0.0741(11) Uani 1 1 d . . . . .
H11A H 0.5589 0.8548 0.5214 0.089 Uiso 1 1 calc R U . . .
H11B H 0.4738 0.9212 0.4513 0.089 Uiso 1 1 calc R U . . .
C15' C 0.6991(10) 0.5588(7) 0.4326(5) 0.0483(15) Uani 0.496(3) 1 d . U P A 2
C13 C 0.1434(5) 0.9528(4) 0.6065(3) 0.0973(15) Uani 1 1 d . . . . .
H13A H 0.0575 0.9252 0.5736 0.146 Uiso 1 1 calc R U . . .
H13B H 0.1223 1.0210 0.6195 0.146 Uiso 1 1 calc R U . . .
H13C H 0.1586 0.9161 0.6592 0.146 Uiso 1 1 calc R U . . .
C17 C 0.7608(14) 0.4639(8) 0.5271(8) 0.070(2) Uani 0.496(3) 1 d . U P A 1
H17 H 0.7698 0.4090 0.5634 0.084 Uiso 0.496(3) 1 calc R U P A 1
C16 C 0.8412(18) 0.5504(9) 0.5466(10) 0.081(3) Uani 0.496(3) 1 d . U P A 1
H16 H 0.9037 0.5559 0.5965 0.097 Uiso 0.496(3) 1 calc R U P A 1
C19' C 0.8744(13) 0.6695(11) 0.5019(6) 0.069(2) Uani 0.496(3) 1 d . U P A 2
H19' H 0.9243 0.7306 0.5045 0.083 Uiso 0.496(3) 1 calc R U P A 2
C18 C 0.6642(10) 0.4600(5) 0.4509(6) 0.0622(18) Uani 0.496(3) 1 d . U P A 1
H18 H 0.6108 0.4017 0.4377 0.075 Uiso 0.496(3) 1 calc R U P A 1
C15 C 0.8247(10) 0.6294(6) 0.4884(6) 0.0528(16) Uani 0.504(3) 1 d . U P A 1
C18' C 0.9091(14) 0.5997(11) 0.5665(6) 0.100(3) Uani 0.504(3) 1 d . U P A 2
H18' H 0.9773 0.6128 0.6129 0.120 Uiso 0.504(3) 1 calc R U P A 2
C17' C 0.834(2) 0.5106(14) 0.5558(9) 0.095(3) Uani 0.504(3) 1 d . U P A 2
H17' H 0.8585 0.4627 0.5974 0.114 Uiso 0.504(3) 1 calc R U P A 2
C16' C 0.7329(13) 0.4832(9) 0.4948(7) 0.077(3) Uani 0.504(3) 1 d . U P A 2
H16' H 0.6876 0.4206 0.4926 0.093 Uiso 0.504(3) 1 calc R U P A 2
C19 C 0.6478(11) 0.5394(5) 0.3966(6) 0.0450(14) Uani 0.504(3) 1 d . U P A 1
H19 H 0.5813 0.5359 0.3482 0.054 Uiso 0.504(3) 1 calc R U P A 1
Cl1' Cl 0.5681(2) 0.53136(13) 0.34959(14) 0.0679(6) Uani 0.504(3) 1 d . . P A 2
C14 C 0.7328(15) 0.6265(9) 0.4149(10) 0.039(2) Uani 0.50(4) 1 d . U P A 1


_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 0.8200 . ?
O1 C8 1.374(3) . ?
Cl1 C15 1.715(9) . ?
O2 H2 0.8200 . ?
O2 C5 1.369(3) . ?
N1 N2 1.348(3) . ?
N1 C3 1.360(3) . ?
N1 C10 1.457(3) . ?
N2 C1 1.330(3) . ?
C4 C2 1.479(3) . ?
C4 C9 1.392(3) . ?
C4 C5 1.395(3) . ?
O4 C12 1.310(4) . ?
O4 C13 1.447(4) . ?
C2 C1 1.390(4) . ?
C2 C3 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.382(3) . ?
C8 C7 1.379(3) . ?
C5 C6 1.385(4) . ?
C1 H1A 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.376(4) . ?
C3 C14' 1.492(11) . ?
C3 C14 1.500(10) . ?
O3 C12 1.182(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.497(5) . ?
C6 H6 0.9300 . ?
C12 C11 1.491(4) . ?
C14' C15' 1.40(2) . ?
C14' C19' 1.37(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15' C16' 1.426(12) . ?
C15' Cl1' 1.724(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.385(19) . ?
C17 C18 1.424(15) . ?
C16 H16 0.9300 . ?
C16 C15 1.400(13) . ?
C19' H19' 0.9300 . ?
C19' C18' 1.399(15) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(10) . ?
C15 C14 1.37(2) . ?
C18' H18' 0.9300 . ?
C18' C17' 1.37(2) . ?
C17' H17' 0.9300 . ?
C17' C16' 1.32(2) . ?
C16' H16' 0.9300 . ?
C19 H19 0.9300 . ?
C19 C14 1.408(19) . ?

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
C8 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
N2 N1 C3 111.5(2) . . ?
N2 N1 C10 120.0(2) . . ?
C3 N1 C10 128.5(2) . . ?
C1 N2 N1 104.9(2) . . ?
C9 C4 C2 121.1(2) . . ?
C9 C4 C5 118.3(2) . . ?
C5 C4 C2 120.6(2) . . ?
C12 O4 C13 116.5(3) . . ?
C1 C2 C4 127.8(2) . . ?
C3 C2 C4 127.7(2) . . ?
C3 C2 C1 104.4(2) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
O1 C8 C9 122.5(2) . . ?
O1 C8 C7 117.7(2) . . ?
C7 C8 C9 119.8(2) . . ?
O2 C5 C4 118.0(2) . . ?
O2 C5 C6 122.0(2) . . ?
C6 C5 C4 120.0(2) . . ?
N2 C1 C2 112.1(2) . . ?
N2 C1 H1A 123.9 . . ?
C2 C1 H1A 123.9 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
N1 C3 C2 107.0(2) . . ?
N1 C3 C14' 122.4(4) . . ?
N1 C3 C14 119.7(4) . . ?
C2 C3 C14' 129.1(5) . . ?
C2 C3 C14 131.7(4) . . ?
N1 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
N1 C10 C11 113.2(2) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
O4 C12 C11 112.5(3) . . ?
O3 C12 O4 123.2(3) . . ?
O3 C12 C11 124.2(3) . . ?
C15' C14' C3 115.6(14) . . ?
C19' C14' C3 127.6(16) . . ?
C19' C14' C15' 116.8(10) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 C10 110.7(3) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C14' C15' C16' 123.0(11) . . ?
C14' C15' Cl1' 119.2(7) . . ?
C16' C15' Cl1' 117.8(9) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.1(9) . . ?
C18 C17 H17 120.4 . . ?
C17 C16 H16 121.3 . . ?
C17 C16 C15 117.4(14) . . ?
C15 C16 H16 121.3 . . ?
C14' C19' H19' 118.5 . . ?
C14' C19' C18' 123.0(16) . . ?
C18' C19' H19' 118.5 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 121.9(9) . . ?
C19 C18 H18 119.0 . . ?
C16 C15 Cl1 115.8(10) . . ?
C14 C15 Cl1 120.2(7) . . ?
C14 C15 C16 124.0(11) . . ?
C19' C18' H18' 122.8 . . ?
C17' C18' C19' 114.4(12) . . ?
C17' C18' H18' 122.8 . . ?
C18' C17' H17' 115.5 . . ?
C16' C17' C18' 129.0(13) . . ?
C16' C17' H17' 115.5 . . ?
C15' C16' H16' 123.2 . . ?
C17' C16' C15' 113.6(13) . . ?
C17' C16' H16' 123.2 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C14 119.1(11) . . ?
C14 C19 H19 120.4 . . ?
C15 C14 C3 116.2(12) . . ?
C15 C14 C19 118.4(8) . . ?
C19 C14 C3 125.3(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 C8 C7 C6 -178.4(3) . . . . ?
Cl1 C15 C14 C3 -3.2(10) . . . . ?
Cl1 C15 C14 C19 179.4(6) . . . . ?
O2 C5 C6 C7 178.3(3) . . . . ?
N1 N2 C1 C2 0.4(4) . . . . ?
N1 C3 C14' C15' 84.5(9) . . . . ?
N1 C3 C14' C19' -97.4(10) . . . . ?
N1 C3 C14 C15 -105.9(8) . . . . ?
N1 C3 C14 C19 71.4(10) . . . . ?
N1 C10 C11 C12 173.7(3) . . . . ?
N2 N1 C3 C2 -0.1(3) . . . . ?
N2 N1 C3 C14' 167.6(11) . . . . ?
N2 N1 C3 C14 -167.5(9) . . . . ?
N2 N1 C10 C11 -71.8(4) . . . . ?
C4 C2 C1 N2 178.6(3) . . . . ?
C4 C2 C3 N1 -178.8(3) . . . . ?
C4 C2 C3 C14' 14.6(12) . . . . ?
C4 C2 C3 C14 -13.4(11) . . . . ?
C4 C9 C8 O1 178.5(3) . . . . ?
C4 C9 C8 C7 -0.3(4) . . . . ?
C4 C5 C6 C7 -1.7(5) . . . . ?
O4 C12 C11 C10 -149.8(4) . . . . ?
C2 C4 C9 C8 178.8(3) . . . . ?
C2 C4 C5 O2 2.2(4) . . . . ?
C2 C4 C5 C6 -177.9(3) . . . . ?
C2 C3 C14' C15' -110.7(9) . . . . ?
C2 C3 C14' C19' 67.4(13) . . . . ?
C2 C3 C14 C15 90.3(11) . . . . ?
C2 C3 C14 C19 -92.5(9) . . . . ?
C9 C4 C2 C1 -130.7(3) . . . . ?
C9 C4 C2 C3 48.1(4) . . . . ?
C9 C4 C5 O2 -178.1(3) . . . . ?
C9 C4 C5 C6 1.9(5) . . . . ?
C9 C8 C7 C6 0.6(5) . . . . ?
C8 C7 C6 C5 0.5(5) . . . . ?
C5 C4 C2 C1 49.0(4) . . . . ?
C5 C4 C2 C3 -132.2(3) . . . . ?
C5 C4 C9 C8 -0.9(4) . . . . ?
C1 C2 C3 N1 0.3(3) . . . . ?
C1 C2 C3 C14' -166.3(11) . . . . ?
C1 C2 C3 C14 165.6(11) . . . . ?
C3 N1 N2 C1 -0.2(3) . . . . ?
C3 N1 C10 C11 107.6(4) . . . . ?
C3 C2 C1 N2 -0.4(4) . . . . ?
C3 C14' C15' C16' 177.1(7) . . . . ?
C3 C14' C15' Cl1' -1.1(9) . . . . ?
C3 C14' C19' C18' -178.9(8) . . . . ?
O3 C12 C11 C10 32.7(6) . . . . ?
C10 N1 N2 C1 179.2(3) . . . . ?
C10 N1 C3 C2 -179.4(3) . . . . ?
C10 N1 C3 C14' -11.7(11) . . . . ?
C10 N1 C3 C14 13.1(10) . . . . ?
C14' C15' C16' C17' 1.7(13) . . . . ?
C14' C19' C18' C17' 2.2(14) . . . . ?
C15' C14' C19' C18' -0.8(13) . . . . ?
C13 O4 C12 O3 -2.8(7) . . . . ?
C13 O4 C12 C11 179.7(4) . . . . ?
C17 C16 C15 Cl1 -177.6(9) . . . . ?
C17 C16 C15 C14 1.1(17) . . . . ?
C17 C18 C19 C14 2.2(11) . . . . ?
C16 C17 C18 C19 -0.4(14) . . . . ?
C16 C15 C14 C3 178.2(9) . . . . ?
C16 C15 C14 C19 0.7(14) . . . . ?
C19' C14' C15' C16' -1.3(12) . . . . ?
C19' C14' C15' Cl1' -179.5(6) . . . . ?
C19' C18' C17' C16' -1.8(19) . . . . ?
C18 C17 C16 C15 -1.2(16) . . . . ?
C18 C19 C14 C3 -179.5(7) . . . . ?
C18 C19 C14 C15 -2.3(11) . . . . ?
C18' C17' C16' C15' 0.0(19) . . . . ?
Cl1' C15' C16' C17' 179.9(8) . . . . ?

_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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.827
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kor_7_100
_database_code_depnum_ccdc_archive 'CCDC 2076749'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(4aR,9bS,10S)-10-(2-chlorophenyl)-9b-nitro-3-oxo-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_name_common            
'(4aR,9bS,10S)-10-(2-chlorophenyl)-9b-nitro-3-oxo-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_formula_moiety         'C20 H16 Cl N3 O6'
_chemical_formula_sum            'C20 H16 Cl N3 O6'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         429.81
_exptl_crystal_recrystallization_method 'frome acetonitrile'
_chemical_melting_point          465-466
_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C20 H16 Cl N3 O6'
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'
Cl Cl 0.3639 0.7018 '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                   18.28800(10)
_cell_length_b                   8.88670(10)
_cell_length_c                   24.7898(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.7630(10)
_cell_angle_gamma                90
_cell_volume                     3767.18(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16680
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1330
_cell_measurement_theta_min      3.6770
_shelx_estimated_absorpt_T_max   0.591
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -4 -10 0.1691
-6 -5 2 0.1585
1 0 -16 0.1305
-4 -3 13 0.1431
-8 -4 7 0.1529
-11 -2 4 0.1636
2 -3 -13 0.1597
-10 0 -4 0.1722
6 -5 -5 0.1811
0 -5 -7 0.1708
-4 0 -12 0.1499
1 4 -10 0.1786
3 -1 -16 0.1451
3 3 10 0.1406
-10 -3 5 0.1549
-7 2 14 0.1953
-12 0 3 0.1760
9 -4 -7 0.1902
-2 -3 13 0.1256
2 1 14 0.1020
2 3 11 0.1356
-3 2 14 0.1476
-6 5 8 0.1944
-10 3 1 0.1824
-4 5 0 0.1706
6 5 -6 0.1581
7 1 -15 0.1378
11 3 -6 0.1598
11 1 -1 0.1597
10 -2 -12 0.1637
2 -5 3 0.1611
4 -4 8 0.1487

_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.266
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
-3.1086 -3.5235 -9.7542 -0.0088 -0.0029 1.0000
-5.5534 -5.0906 1.7899 -0.1643 -0.6943 0.7006
1.2635 0.3864 -15.5256 0.1727 0.7159 0.6765
-4.2985 -3.3453 13.0384 -0.2315 -0.9675 -0.1020
-8.2738 -3.9520 7.1746 0.0723 -0.8956 0.4390
-11.2664 -1.7434 4.0525 0.5627 -0.6559 0.5032
2.1209 -3.1152 -13.3935 -0.2870 0.3385 0.8961
-9.8986 -0.2967 -3.5139 0.7255 -0.1719 0.6664
5.9460 -4.9382 -4.8121 -0.8744 -0.0686 0.4803
-0.4122 -5.0129 -7.2436 -0.3937 -0.1614 0.9049
-3.9416 0.2752 -12.2750 0.4860 0.4180 0.7675
1.2193 4.4061 -10.1697 0.5217 0.8531 -0.0092
3.1101 -0.6010 -15.9226 -0.0571 0.6981 0.7137
3.0809 3.4672 9.8977 0.0028 -0.0089 -1.0000
-9.9757 -3.1287 4.6249 0.3168 -0.7659 0.5594
-7.1007 2.0861 14.1668 0.5231 -0.6093 -0.5959
-11.6375 -0.2111 2.6706 0.7700 -0.4720 0.4293
8.5988 -3.7874 -7.3041 -0.9071 0.2160 0.3613
-1.7216 -3.4616 12.6565 -0.4222 -0.8863 -0.1905
1.8276 1.2817 13.6039 -0.1905 -0.3956 -0.8984
2.2366 3.3754 10.7964 0.0406 -0.0793 -0.9960
-2.7164 2.4728 14.4526 0.2468 -0.4576 -0.8542
-5.5668 4.5958 8.4215 0.7597 -0.1007 -0.6424
-10.2484 2.5785 1.3993 0.9823 -0.1281 0.1367
-4.3571 5.2842 -0.3665 0.8715 0.3612 -0.3316
5.5783 4.9154 -6.1657 0.2068 0.8609 -0.4649
7.4232 1.3371 -14.7689 -0.1777 0.9510 0.2532
10.6737 2.5220 -5.5248 -0.4175 0.7694 -0.4835
11.1647 1.2365 -1.3902 -0.6469 0.4969 -0.5785
9.5096 -2.1643 -11.5815 -0.7403 0.5659 0.3630
2.4780 -5.3827 3.2274 -0.7888 -0.5440 0.2863
4.0768 -3.8407 8.0036 -0.8092 -0.5568 -0.1878

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21644
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.301
_diffrn_reflns_theta_min         3.814
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 150.00  100
  2  ω     27.00  97.00   1.00    1.00    --   41.35-125.00   0.00   70
  3  ω     27.00  97.00   1.00    1.00    --   41.35-125.00 150.00   70
  4  ω    103.00 178.00   1.00    1.14    --  112.00  77.00 -30.00   75
  5  ω     30.00 106.00   1.00    1.14    --  112.00 -95.00 150.00   76
  6  ω     39.00 138.00   1.00    1.14    --  112.00 -45.00   0.00   99
  7  ω     36.00 109.00   1.00    1.14    --  112.00-111.00 120.00   73
  8  ω    104.00 178.00   1.00    1.14    --  112.00 111.00  60.00   74
  9  ω     36.00 109.00   1.00    1.14    --  112.00-111.00   0.00   73
 10  ω     30.00 106.00   1.00    1.14    --  112.00 -95.00  30.00   76
 11  ω     83.00 178.00   1.00    1.14    --  112.00  61.00  90.00   95
 12  ω     36.00 140.00   1.00    1.14    --  112.00 -30.00-180.00  104
 13  ω     36.00 109.00   1.00    1.14    --  112.00-111.00  90.00   73
 14  ω     84.00 178.00   1.00    1.14    --  112.00  30.00  30.00   94
 15  ω    -74.00  35.00   1.00    1.00    --  -41.35  77.00   0.00  109
 16  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00  30.00  100
 17  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -90.00  100
 18  ω     36.00 145.00   1.00    1.14    --  112.00 -77.00 150.00  109
 19  ω     59.00 178.00   1.00    1.14    --  112.00  15.00 -60.00  119
 20  ω     84.00 178.00   1.00    1.14    --  112.00  55.00 -37.00   94
 21  ω     86.00 139.00   1.00    1.14    --  112.00  45.00  60.00   53
 22  ω     84.00 178.00   1.00    1.14    --  112.00  30.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0713612000
_diffrn_orient_matrix_UB_12      0.1050986000
_diffrn_orient_matrix_UB_13      -0.0143183000
_diffrn_orient_matrix_UB_21      0.0294070000
_diffrn_orient_matrix_UB_22      0.0897262000
_diffrn_orient_matrix_UB_23      -0.0414853000
_diffrn_orient_matrix_UB_31      -0.0464562000
_diffrn_orient_matrix_UB_32      -0.1045212000
_diffrn_orient_matrix_UB_33      -0.0499543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3834
_reflns_number_total             3899
_reflns_odcompleteness_completeness 97.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00083(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+3.8008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0742
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C18(H18), C9(H9), C17(H17), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.89482(2) 0.76641(3) 0.57730(2) 0.02234(10) Uani 1 1 d . . . . .
O1 O 0.74181(5) 0.37309(9) 0.70726(3) 0.01630(18) Uani 1 1 d . . . . .
O3 O 0.53661(5) 0.66420(10) 0.51879(3) 0.01809(18) Uani 1 1 d . . . . .
O6 O 0.90815(5) 0.39479(10) 0.63422(4) 0.0217(2) Uani 1 1 d . . . . .
O2 O 0.97051(5) 0.32280(10) 0.78750(4) 0.01994(19) Uani 1 1 d . . . . .
O5 O 0.80197(5) 0.43170(12) 0.56050(4) 0.0256(2) Uani 1 1 d . . . . .
O4 O 0.51291(7) 0.84567(12) 0.57375(4) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.86583(5) 0.48462(11) 0.75354(4) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.84082(6) 0.44078(11) 0.61164(4) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.85267(6) 0.64288(11) 0.74070(4) 0.0145(2) Uani 1 1 d . . . . .
C12 C 0.71785(6) 0.52623(13) 0.62707(5) 0.0134(2) Uani 1 1 d . . . . .
C7 C 0.68702(7) 0.44456(13) 0.66161(5) 0.0142(2) Uani 1 1 d . . . . .
C11 C 0.66860(7) 0.60484(13) 0.57932(5) 0.0152(2) Uani 1 1 d . . . . .
H11 H 0.6886 0.6627 0.5554 0.018 Uiso 1 1 calc R U . . .
C13 C 0.82013(6) 0.80427(13) 0.65439(5) 0.0139(2) Uani 1 1 d . . . . .
C8 C 0.60737(7) 0.43343(13) 0.65054(5) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.5874 0.3759 0.6745 0.020 Uiso 1 1 calc R U . . .
C10 C 0.58916(7) 0.59449(13) 0.56840(5) 0.0156(2) Uani 1 1 d . . . . .
C18 C 0.77149(7) 0.88775(14) 0.67567(5) 0.0176(2) Uani 1 1 d . . . . .
H18 H 0.7583 0.8487 0.7067 0.021 Uiso 1 1 calc R U . . .
C9 C 0.55831(7) 0.51057(14) 0.60263(5) 0.0171(2) Uani 1 1 d . . . . .
H9 H 0.5033 0.5060 0.5932 0.021 Uiso 1 1 calc R U . . .
C3 C 0.85338(6) 0.65493(13) 0.68077(5) 0.0130(2) Uani 1 1 d . . . . .
H3 H 0.9081 0.6443 0.6815 0.016 Uiso 1 1 calc R U . . .
C1 C 0.81747(6) 0.40185(13) 0.70453(5) 0.0143(2) Uani 1 1 d . . . . .
H1 H 0.8434 0.3066 0.6995 0.017 Uiso 1 1 calc R U . . .
C14 C 0.83741(7) 0.86561(14) 0.60831(5) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.80475(6) 0.51247(13) 0.65232(5) 0.0130(2) Uani 1 1 d . . . . .
C5 C 0.98754(7) 0.59731(14) 0.79961(5) 0.0192(2) Uani 1 1 d . . . . .
H5A H 1.0226 0.6183 0.7779 0.023 Uiso 1 1 calc R U . . .
H5B H 1.0187 0.5965 0.8414 0.023 Uiso 1 1 calc R U . . .
C6 C 0.94493(7) 0.45026(14) 0.78083(5) 0.0157(2) Uani 1 1 d . . . . .
C17 C 0.74208(7) 1.02678(14) 0.65226(6) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.7089 1.0817 0.6672 0.025 Uiso 1 1 calc R U . . .
C15 C 0.80904(7) 1.00479(14) 0.58485(5) 0.0195(2) Uani 1 1 d . . . . .
H15 H 0.8222 1.0445 0.5539 0.023 Uiso 1 1 calc R U . . .
C4 C 0.92155(7) 0.71340(14) 0.78549(5) 0.0184(2) Uani 1 1 d . . . . .
H4A H 0.9094 0.7378 0.8204 0.022 Uiso 1 1 calc R U . . .
H4B H 0.9367 0.8072 0.7706 0.022 Uiso 1 1 calc R U . . .
C16 C 0.76120(7) 1.08543(14) 0.60703(5) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.7415 1.1809 0.5913 0.025 Uiso 1 1 calc R U . . .
C19 C 0.49745(7) 0.78650(14) 0.52770(5) 0.0206(3) Uani 1 1 d . . . . .
C20 C 0.43434(8) 0.83228(17) 0.47300(6) 0.0305(3) Uani 1 1 d . . . . .
H20A H 0.4573 0.8556 0.4438 0.046 Uiso 1 1 calc R U . . .
H20B H 0.4075 0.9215 0.4800 0.046 Uiso 1 1 calc R U . . .
H20C H 0.3967 0.7498 0.4593 0.046 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
Cl1 C14 1.7442(12) . ?
O1 C7 1.3726(14) . ?
O1 C1 1.4321(13) . ?
O3 C10 1.4078(13) . ?
O3 C19 1.3620(15) . ?
O6 N3 1.2280(13) . ?
O2 C6 1.2142(15) . ?
O5 N3 1.2166(13) . ?
O4 C19 1.1962(16) . ?
N1 N2 1.4432(13) . ?
N1 C1 1.4274(14) . ?
N1 C6 1.3964(14) . ?
N3 C2 1.5262(14) . ?
N2 C3 1.4941(14) . ?
N2 C4 1.4903(14) . ?
C12 C7 1.3856(16) . ?
C12 C11 1.3944(16) . ?
C12 C2 1.4925(15) . ?
C7 C8 1.3870(16) . ?
C11 H11 0.9500 . ?
C11 C10 1.3833(16) . ?
C13 C18 1.3974(16) . ?
C13 C3 1.5089(16) . ?
C13 C14 1.3993(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3892(17) . ?
C10 C9 1.3906(17) . ?
C18 H18 0.9500 . ?
C18 C17 1.3897(17) . ?
C9 H9 0.9500 . ?
C3 H3 1.0000 . ?
C3 C2 1.5640(15) . ?
C1 H1 1.0000 . ?
C1 C2 1.5754(15) . ?
C14 C15 1.3868(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5081(17) . ?
C5 C4 1.5310(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.3889(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3865(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C16 H16 0.9500 . ?
C19 C20 1.4921(17) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C7 O1 C1 108.27(8) . . ?
C19 O3 C10 116.41(9) . . ?
C1 N1 N2 108.05(8) . . ?
C6 N1 N2 112.52(9) . . ?
C6 N1 C1 121.50(10) . . ?
O6 N3 C2 115.86(9) . . ?
O5 N3 O6 125.00(10) . . ?
O5 N3 C2 119.13(9) . . ?
N1 N2 C3 103.28(8) . . ?
N1 N2 C4 102.40(8) . . ?
C4 N2 C3 114.07(9) . . ?
C7 C12 C11 120.34(10) . . ?
C7 C12 C2 107.69(10) . . ?
C11 C12 C2 131.94(10) . . ?
O1 C7 C12 114.45(10) . . ?
O1 C7 C8 122.60(10) . . ?
C12 C7 C8 122.95(11) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 C12 116.76(10) . . ?
C10 C11 H11 121.6 . . ?
C18 C13 C3 121.06(10) . . ?
C18 C13 C14 117.36(11) . . ?
C14 C13 C3 121.57(10) . . ?
C7 C8 H8 121.7 . . ?
C7 C8 C9 116.66(11) . . ?
C9 C8 H8 121.7 . . ?
C11 C10 O3 119.08(10) . . ?
C11 C10 C9 122.78(11) . . ?
C9 C10 O3 118.04(10) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.22(11) . . ?
C17 C18 H18 119.4 . . ?
C8 C9 C10 120.50(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C3 C13 110.47(9) . . ?
N2 C3 H3 109.7 . . ?
N2 C3 C2 100.74(8) . . ?
C13 C3 H3 109.7 . . ?
C13 C3 C2 116.06(9) . . ?
C2 C3 H3 109.7 . . ?
O1 C1 H1 111.4 . . ?
O1 C1 C2 106.65(8) . . ?
N1 C1 O1 111.66(9) . . ?
N1 C1 H1 111.4 . . ?
N1 C1 C2 104.13(9) . . ?
C2 C1 H1 111.4 . . ?
C13 C14 Cl1 120.55(9) . . ?
C15 C14 Cl1 117.40(9) . . ?
C15 C14 C13 122.04(11) . . ?
N3 C2 C3 109.03(8) . . ?
N3 C2 C1 108.05(9) . . ?
C12 C2 N3 113.73(9) . . ?
C12 C2 C3 118.26(9) . . ?
C12 C2 C1 102.76(9) . . ?
C3 C2 C1 103.88(8) . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C6 C5 C4 103.54(9) . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
O2 C6 N1 123.57(11) . . ?
O2 C6 C5 129.37(11) . . ?
N1 C6 C5 107.05(10) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.98(11) . . ?
C16 C17 H17 120.0 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.31(11) . . ?
C16 C15 H15 120.3 . . ?
N2 C4 C5 106.05(9) . . ?
N2 C4 H4A 110.5 . . ?
N2 C4 H4B 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.07(11) . . ?
C15 C16 H16 120.0 . . ?
O3 C19 C20 110.61(11) . . ?
O4 C19 O3 123.06(12) . . ?
O4 C19 C20 126.33(12) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
Cl1 C14 C15 C16 178.04(9) . . . . ?
O1 C7 C8 C9 -179.51(10) . . . . ?
O1 C1 C2 N3 -124.74(9) . . . . ?
O1 C1 C2 C12 -4.23(11) . . . . ?
O1 C1 C2 C3 119.56(9) . . . . ?
O3 C10 C9 C8 176.90(10) . . . . ?
O6 N3 C2 C12 -163.44(10) . . . . ?
O6 N3 C2 C3 62.23(12) . . . . ?
O6 N3 C2 C1 -50.06(12) . . . . ?
O5 N3 C2 C12 15.87(14) . . . . ?
O5 N3 C2 C3 -118.46(11) . . . . ?
O5 N3 C2 C1 129.26(11) . . . . ?
N1 N2 C3 C13 165.43(8) . . . . ?
N1 N2 C3 C2 42.19(10) . . . . ?
N1 N2 C4 C5 28.77(11) . . . . ?
N1 C1 C2 N3 117.06(9) . . . . ?
N1 C1 C2 C12 -122.43(9) . . . . ?
N1 C1 C2 C3 1.36(11) . . . . ?
N2 N1 C1 O1 -88.81(10) . . . . ?
N2 N1 C1 C2 25.89(11) . . . . ?
N2 N1 C6 O2 -168.19(10) . . . . ?
N2 N1 C6 C5 12.80(12) . . . . ?
N2 C3 C2 N3 -141.25(9) . . . . ?
N2 C3 C2 C12 86.78(11) . . . . ?
N2 C3 C2 C1 -26.25(10) . . . . ?
C12 C7 C8 C9 -0.71(17) . . . . ?
C12 C11 C10 O3 -176.22(10) . . . . ?
C12 C11 C10 C9 -0.03(17) . . . . ?
C7 O1 C1 N1 116.84(10) . . . . ?
C7 O1 C1 C2 3.70(12) . . . . ?
C7 C12 C11 C10 -0.96(17) . . . . ?
C7 C12 C2 N3 119.78(10) . . . . ?
C7 C12 C2 C3 -110.38(11) . . . . ?
C7 C12 C2 C1 3.26(12) . . . . ?
C7 C8 C9 C10 -0.30(17) . . . . ?
C11 C12 C7 O1 -179.74(10) . . . . ?
C11 C12 C7 C8 1.38(18) . . . . ?
C11 C12 C2 N3 -61.93(16) . . . . ?
C11 C12 C2 C3 67.91(16) . . . . ?
C11 C12 C2 C1 -178.45(12) . . . . ?
C11 C10 C9 C8 0.68(18) . . . . ?
C13 C18 C17 C16 -0.28(18) . . . . ?
C13 C3 C2 N3 99.47(11) . . . . ?
C13 C3 C2 C12 -32.50(14) . . . . ?
C13 C3 C2 C1 -145.52(9) . . . . ?
C13 C14 C15 C16 -0.87(18) . . . . ?
C10 O3 C19 O4 9.54(18) . . . . ?
C10 O3 C19 C20 -170.09(11) . . . . ?
C18 C13 C3 N2 -21.07(14) . . . . ?
C18 C13 C3 C2 92.76(12) . . . . ?
C18 C13 C14 Cl1 -177.73(9) . . . . ?
C18 C13 C14 C15 1.14(17) . . . . ?
C18 C17 C16 C15 0.58(19) . . . . ?
C3 N2 C4 C5 -82.06(11) . . . . ?
C3 C13 C18 C17 178.65(11) . . . . ?
C3 C13 C14 Cl1 3.06(15) . . . . ?
C3 C13 C14 C15 -178.07(10) . . . . ?
C1 O1 C7 C12 -1.70(13) . . . . ?
C1 O1 C7 C8 177.18(10) . . . . ?
C1 N1 N2 C3 -44.55(11) . . . . ?
C1 N1 N2 C4 -163.29(9) . . . . ?
C1 N1 C6 O2 -37.82(16) . . . . ?
C1 N1 C6 C5 143.17(10) . . . . ?
C14 C13 C18 C17 -0.56(17) . . . . ?
C14 C13 C3 N2 158.11(10) . . . . ?
C14 C13 C3 C2 -88.06(13) . . . . ?
C14 C15 C16 C17 -0.02(18) . . . . ?
C2 C12 C7 O1 -1.21(13) . . . . ?
C2 C12 C7 C8 179.90(11) . . . . ?
C2 C12 C11 C10 -179.07(11) . . . . ?
C6 N1 N2 C3 92.35(10) . . . . ?
C6 N1 N2 C4 -26.39(11) . . . . ?
C6 N1 C1 O1 138.95(10) . . . . ?
C6 N1 C1 C2 -106.36(11) . . . . ?
C6 C5 C4 N2 -21.89(12) . . . . ?
C4 N2 C3 C13 -84.27(11) . . . . ?
C4 N2 C3 C2 152.49(9) . . . . ?
C4 C5 C6 O2 -172.79(12) . . . . ?
C4 C5 C6 N1 6.15(12) . . . . ?
C19 O3 C10 C11 -110.58(12) . . . . ?
C19 O3 C10 C9 73.05(14) . . . . ?

_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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.826
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'I 2/a'
_symmetry_int_tables_number      15
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kor_6_100_2
_database_code_depnum_ccdc_archive 'CCDC 2076734'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(4aR,9bS,10S)-10-(4-methoxyphenyl)-9b-nitro-3-oxo-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_name_common            
'(4aR,9bS,10S)-10-(4-methoxyphenyl)-9b-nitro-3-oxo-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_formula_moiety         'C21 H19 N3 O7'
_chemical_formula_sum            'C21 H19 N3 O7'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         425.39
_exptl_crystal_recrystallization_method 'from CHCl3/CCl4'
_chemical_melting_point          447-448
_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C21 H19 N3 O7'
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                   14.40077(10)
_cell_length_b                   16.91016(12)
_cell_length_c                   8.11294(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.4865(6)
_cell_angle_gamma                90
_cell_volume                     1974.99(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13416
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0340
_cell_measurement_theta_min      4.0140
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -11 0 0.1965
2 0 -5 0.2028
0 2 5 0.2430
-9 0 0 0.0250
-2 0 5 0.2357
1 11 0 0.2013
9 0 0 0.0250
-9 0 0 0.0250

_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.401
_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
-0.8211 -10.9344 0.0386 -0.6425 0.7503 0.1555
2.1418 0.3989 -5.1522 0.1389 -0.1655 0.9764
-0.2771 1.9550 5.1840 0.1477 0.1044 -0.9835
-9.3305 0.1083 -0.1477 -0.8130 -0.5595 -0.1610
-2.1199 0.4714 5.1534 -0.0915 0.1035 -0.9904
0.8455 10.9299 -0.1134 0.6434 -0.7524 -0.1412
9.3203 -0.0794 0.2427 0.8149 0.5616 0.1430
-9.3203 0.0794 -0.2427 -0.8149 -0.5616 -0.1430

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.418
_diffrn_reflns_theta_min         3.070
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00  60.00  100
  2  ω      7.00  34.00   1.00    1.00    --   41.35  83.00 -18.15   27
  3  ω      7.00  33.00   1.00    1.00    --   41.35  84.00-129.65   26
  4  ω    -33.00  66.00   1.00    1.00    --   41.35 -38.00-150.00   99
  5  ω      7.00  34.00   1.00    1.00    --   41.35  83.00  50.36   27
  6  ω    104.00 178.00   1.00    1.29    --  112.00 111.00 -90.00   74
  7  ω     40.00 141.00   1.00    1.29    --  112.00 -61.00 -90.00  101
  8  ω     59.00 178.00   1.00    1.29    --  112.00  15.00   0.00  119
  9  ω     86.00 178.00   1.00    1.29    --  112.00  45.00   0.00   92
 10  ω     36.00 109.00   1.00    1.29    --  112.00-111.00 -60.00   73
 11  ω     30.00 106.00   1.00    1.29    --  112.00 -95.00 -30.00   76
 12  ω     84.00 178.00   1.00    1.29    --  112.00  30.00 -90.00   94
 13  ω    103.00 178.00   1.00    1.29    --  112.00  77.00 120.00   75
 14  ω     86.00 178.00   1.00    1.29    --  112.00  45.00  30.00   92
 15  ω     36.00 145.00   1.00    1.29    --  112.00 -77.00 -90.00  109
 16  ω    104.00 178.00   1.00    1.29    --  112.00 111.00  30.00   74
 17  ω    104.00 178.00   1.00    1.29    --  112.00 111.00   0.00   74
 18  ω     30.00 106.00   1.00    1.29    --  112.00 -95.00-150.00   76
 19  ω    104.00 178.00   1.00    1.29    --  112.00 111.00-120.00   74
 20  ω     36.00 109.00   1.00    1.29    --  112.00-111.00 -90.00   73
 21  ω    109.00 178.00   1.00    1.29    --  112.00 111.00  90.00   69
 22  ω    148.00 177.00   1.00    1.29    --  112.00  77.00 -30.00   29
 23  ω     76.00 101.00   1.00    1.29    --  112.00 -95.00-120.00   25
 24  ω     42.00  70.00   1.00    1.29    --  112.00-111.00  90.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0875322000
_diffrn_orient_matrix_UB_12      0.0522356000
_diffrn_orient_matrix_UB_13      0.0134774000
_diffrn_orient_matrix_UB_21      0.0583160000
_diffrn_orient_matrix_UB_22      -0.0728212000
_diffrn_orient_matrix_UB_23      0.0507239000
_diffrn_orient_matrix_UB_31      0.0199526000
_diffrn_orient_matrix_UB_32      -0.0163604000
_diffrn_orient_matrix_UB_33      -0.1824822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3892
_reflns_number_total             4136
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.7063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C17(H17), C18(H18), C14(H14), C15(H15), C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.37513(5) 0.72153(5) 0.46111(10) 0.01977(19) Uani 1 1 d . . . . .
O1 O 0.63902(5) 0.77381(4) 0.39890(10) 0.01727(18) Uani 1 1 d . . . . .
O3 O 0.97426(6) 0.62910(5) 0.29509(10) 0.02122(19) Uani 1 1 d . . . . .
O7 O 0.70471(6) 0.55432(5) 0.65329(10) 0.02116(19) Uani 1 1 d . . . . .
O6 O 0.56054(6) 0.58883(5) 0.67923(10) 0.0225(2) Uani 1 1 d . . . . .
O5 O 0.83348(6) 0.36643(5) 0.02296(10) 0.0242(2) Uani 1 1 d . . . . .
O4 O 1.00690(7) 0.61689(7) 0.56647(11) 0.0314(2) Uani 1 1 d . . . . .
N1 N 0.54237(6) 0.63841(5) 0.20491(11) 0.01368(19) Uani 1 1 d . . . . .
N3 N 0.63484(6) 0.58997(5) 0.60778(11) 0.01456(19) Uani 1 1 d . . . . .
N2 N 0.50827(6) 0.69746(5) 0.31773(11) 0.01365(19) Uani 1 1 d . . . . .
C13 C 0.64456(7) 0.51984(6) 0.23257(13) 0.0137(2) Uani 1 1 d . . . . .
C12 C 0.73127(7) 0.66145(6) 0.39998(12) 0.0137(2) Uani 1 1 d . . . . .
C11 C 0.81445(8) 0.62177(7) 0.37666(13) 0.0157(2) Uani 1 1 d . . . . .
H11 H 0.8194 0.5674 0.3925 0.019 Uiso 1 1 calc R U . . .
C17 C 0.72039(8) 0.39151(6) 0.23601(14) 0.0172(2) Uani 1 1 d . . . . .
H17 H 0.7285 0.3418 0.2831 0.021 Uiso 1 1 calc R U . . .
C7 C 0.72564(7) 0.74254(6) 0.37374(13) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.57786(7) 0.71071(6) 0.44406(13) 0.0139(2) Uani 1 1 d . . . . .
H1 H 0.5503 0.7202 0.5515 0.017 Uiso 1 1 calc R U . . .
C10 C 0.88960(8) 0.66662(7) 0.32879(13) 0.0177(2) Uani 1 1 d . . . . .
C6 C 0.41472(7) 0.68802(6) 0.35040(13) 0.0148(2) Uani 1 1 d . . . . .
C18 C 0.65754(7) 0.44504(6) 0.30071(13) 0.0153(2) Uani 1 1 d . . . . .
H18 H 0.6234 0.4305 0.3916 0.018 Uiso 1 1 calc R U . . .
C3 C 0.58362(7) 0.57837(6) 0.31694(12) 0.0129(2) Uani 1 1 d . . . . .
H3 H 0.5340 0.5502 0.3728 0.016 Uiso 1 1 calc R U . . .
C16 C 0.77088(8) 0.41375(7) 0.09972(13) 0.0176(2) Uani 1 1 d . . . . .
C14 C 0.69452(8) 0.54084(7) 0.09383(13) 0.0174(2) Uani 1 1 d . . . . .
H14 H 0.6855 0.5902 0.0453 0.021 Uiso 1 1 calc R U . . .
C2 C 0.63683(7) 0.63312(6) 0.44410(12) 0.0128(2) Uani 1 1 d . . . . .
C15 C 0.75730(8) 0.48826(7) 0.02871(13) 0.0198(2) Uani 1 1 d . . . . .
H15 H 0.7908 0.5026 -0.0631 0.024 Uiso 1 1 calc R U . . .
C4 C 0.45694(8) 0.61102(7) 0.11389(13) 0.0171(2) Uani 1 1 d . . . . .
H4A H 0.4595 0.5544 0.0953 0.021 Uiso 1 1 calc R U . . .
H4B H 0.4509 0.6374 0.0080 0.021 Uiso 1 1 calc R U . . .
C9 C 0.88389(8) 0.74767(7) 0.30201(14) 0.0204(2) Uani 1 1 d . . . . .
H9 H 0.9358 0.7755 0.2685 0.025 Uiso 1 1 calc R U . . .
C5 C 0.37476(8) 0.63187(7) 0.22225(14) 0.0179(2) Uani 1 1 d . . . . .
H5A H 0.3255 0.6571 0.1576 0.021 Uiso 1 1 calc R U . . .
H5B H 0.3501 0.5849 0.2738 0.021 Uiso 1 1 calc R U . . .
C19 C 1.02822(8) 0.60639(7) 0.42656(14) 0.0184(2) Uani 1 1 d . . . . .
C8 C 0.80067(8) 0.78716(7) 0.32529(14) 0.0197(2) Uani 1 1 d . . . . .
H8 H 0.7956 0.8414 0.3089 0.024 Uiso 1 1 calc R U . . .
C20 C 1.11509(8) 0.56725(8) 0.37041(16) 0.0245(3) Uani 1 1 d . . . . .
H20A H 1.1022 0.5130 0.3433 0.037 Uiso 1 1 calc R U . . .
H20B H 1.1617 0.5695 0.4571 0.037 Uiso 1 1 calc R U . . .
H20C H 1.1372 0.5941 0.2748 0.037 Uiso 1 1 calc R U . . .
C21 C 0.85538(9) 0.29212(8) 0.09783(16) 0.0264(3) Uani 1 1 d . . . . .
H21A H 0.9024 0.2661 0.0361 0.040 Uiso 1 1 calc R U . . .
H21B H 0.8006 0.2597 0.0989 0.040 Uiso 1 1 calc R U . . .
H21C H 0.8778 0.3006 0.2089 0.040 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
O2 C6 1.2164(14) . ?
O1 C7 1.3750(13) . ?
O1 C1 1.4371(12) . ?
O3 C10 1.4074(13) . ?
O3 C19 1.3587(14) . ?
O7 N3 1.2218(13) . ?
O6 N3 1.2303(12) . ?
O5 C16 1.3673(13) . ?
O5 C21 1.4275(15) . ?
O4 C19 1.1968(15) . ?
N1 N2 1.4489(12) . ?
N1 C3 1.4772(13) . ?
N1 C4 1.4921(14) . ?
N3 C2 1.5161(13) . ?
N2 C1 1.4323(14) . ?
N2 C6 1.3890(13) . ?
C13 C18 1.3911(15) . ?
C13 C3 1.4998(14) . ?
C13 C14 1.3973(15) . ?
C12 C11 1.3902(15) . ?
C12 C7 1.3897(15) . ?
C12 C2 1.4943(14) . ?
C11 H11 0.9300 . ?
C11 C10 1.3853(15) . ?
C17 H17 0.9300 . ?
C17 C18 1.3925(15) . ?
C17 C16 1.3909(16) . ?
C7 C8 1.3832(15) . ?
C1 H1 0.9800 . ?
C1 C2 1.5629(14) . ?
C10 C9 1.3899(17) . ?
C6 C5 1.5108(15) . ?
C18 H18 0.9300 . ?
C3 H3 0.9800 . ?
C3 C2 1.5709(14) . ?
C16 C15 1.3971(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3826(16) . ?
C15 H15 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5335(15) . ?
C9 H9 0.9300 . ?
C9 C8 1.3891(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C19 C20 1.4967(15) . ?
C8 H8 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C7 O1 C1 108.47(8) . . ?
C19 O3 C10 117.10(8) . . ?
C16 O5 C21 117.54(9) . . ?
N2 N1 C3 102.85(7) . . ?
N2 N1 C4 103.77(8) . . ?
C3 N1 C4 113.85(8) . . ?
O7 N3 O6 124.71(9) . . ?
O7 N3 C2 117.91(8) . . ?
O6 N3 C2 117.17(9) . . ?
C1 N2 N1 108.51(8) . . ?
C6 N2 N1 112.81(8) . . ?
C6 N2 C1 123.06(9) . . ?
C18 C13 C3 119.52(9) . . ?
C18 C13 C14 118.98(10) . . ?
C14 C13 C3 121.31(9) . . ?
C11 C12 C2 132.12(10) . . ?
C7 C12 C11 120.16(10) . . ?
C7 C12 C2 107.65(9) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 C12 117.13(10) . . ?
C10 C11 H11 121.4 . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.83(10) . . ?
O1 C7 C12 113.97(9) . . ?
O1 C7 C8 123.42(10) . . ?
C8 C7 C12 122.61(10) . . ?
O1 C1 H1 111.7 . . ?
O1 C1 C2 106.66(8) . . ?
N2 C1 O1 110.84(8) . . ?
N2 C1 H1 111.7 . . ?
N2 C1 C2 103.83(8) . . ?
C2 C1 H1 111.7 . . ?
C11 C10 O3 119.65(10) . . ?
C11 C10 C9 122.70(10) . . ?
C9 C10 O3 117.53(10) . . ?
O2 C6 N2 124.25(10) . . ?
O2 C6 C5 128.58(10) . . ?
N2 C6 C5 107.15(9) . . ?
C13 C18 C17 121.55(10) . . ?
C13 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
N1 C3 C13 113.80(8) . . ?
N1 C3 H3 109.4 . . ?
N1 C3 C2 100.40(8) . . ?
C13 C3 H3 109.4 . . ?
C13 C3 C2 114.04(8) . . ?
C2 C3 H3 109.4 . . ?
O5 C16 C17 124.63(11) . . ?
O5 C16 C15 115.27(10) . . ?
C17 C16 C15 120.08(10) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.99(10) . . ?
C15 C14 H14 120.0 . . ?
N3 C2 C1 112.44(8) . . ?
N3 C2 C3 105.76(8) . . ?
C12 C2 N3 113.71(8) . . ?
C12 C2 C1 103.22(8) . . ?
C12 C2 C3 117.59(8) . . ?
C1 C2 C3 103.82(8) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.55(10) . . ?
C14 C15 H15 119.7 . . ?
N1 C4 H4A 110.4 . . ?
N1 C4 H4B 110.4 . . ?
N1 C4 C5 106.47(8) . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.04(10) . . ?
C8 C9 H9 120.0 . . ?
C6 C5 C4 104.67(9) . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
O3 C19 C20 110.58(10) . . ?
O4 C19 O3 123.16(11) . . ?
O4 C19 C20 126.25(11) . . ?
C7 C8 C9 117.35(11) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 H8 121.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O2 C6 C5 C4 178.41(11) . . . . ?
O1 C7 C8 C9 -179.06(10) . . . . ?
O1 C1 C2 N3 124.13(9) . . . . ?
O1 C1 C2 C12 1.18(10) . . . . ?
O1 C1 C2 C3 -122.03(8) . . . . ?
O3 C10 C9 C8 176.80(10) . . . . ?
O7 N3 C2 C12 -29.36(13) . . . . ?
O7 N3 C2 C1 -146.21(9) . . . . ?
O7 N3 C2 C3 101.15(10) . . . . ?
O6 N3 C2 C12 155.71(9) . . . . ?
O6 N3 C2 C1 38.86(12) . . . . ?
O6 N3 C2 C3 -73.78(11) . . . . ?
O5 C16 C15 C14 178.92(11) . . . . ?
N1 N2 C1 O1 91.14(9) . . . . ?
N1 N2 C1 C2 -23.04(10) . . . . ?
N1 N2 C6 O2 167.01(10) . . . . ?
N1 N2 C6 C5 -14.46(11) . . . . ?
N1 C3 C2 N3 148.18(8) . . . . ?
N1 C3 C2 C12 -83.59(10) . . . . ?
N1 C3 C2 C1 29.64(9) . . . . ?
N1 C4 C5 C6 13.54(11) . . . . ?
N2 N1 C3 C13 -165.91(8) . . . . ?
N2 N1 C3 C2 -43.67(9) . . . . ?
N2 N1 C4 C5 -21.37(10) . . . . ?
N2 C1 C2 N3 -118.74(9) . . . . ?
N2 C1 C2 C12 118.31(8) . . . . ?
N2 C1 C2 C3 -4.90(10) . . . . ?
N2 C6 C5 C4 -0.03(11) . . . . ?
C13 C3 C2 N3 -89.74(10) . . . . ?
C13 C3 C2 C12 38.49(12) . . . . ?
C13 C3 C2 C1 151.72(8) . . . . ?
C13 C14 C15 C16 0.49(18) . . . . ?
C12 C11 C10 O3 -176.74(9) . . . . ?
C12 C11 C10 C9 -0.90(17) . . . . ?
C12 C7 C8 C9 0.37(17) . . . . ?
C11 C12 C7 O1 179.05(9) . . . . ?
C11 C12 C7 C8 -0.43(16) . . . . ?
C11 C12 C2 N3 59.29(15) . . . . ?
C11 C12 C2 C1 -178.61(11) . . . . ?
C11 C12 C2 C3 -65.06(15) . . . . ?
C11 C10 C9 C8 0.88(18) . . . . ?
C17 C16 C15 C14 0.69(18) . . . . ?
C7 O1 C1 N2 -112.66(9) . . . . ?
C7 O1 C1 C2 -0.28(11) . . . . ?
C7 C12 C11 C10 0.66(16) . . . . ?
C7 C12 C2 N3 -123.76(9) . . . . ?
C7 C12 C2 C1 -1.66(11) . . . . ?
C7 C12 C2 C3 111.90(10) . . . . ?
C1 O1 C7 C12 -0.86(12) . . . . ?
C1 O1 C7 C8 178.61(10) . . . . ?
C1 N2 C6 O2 33.80(16) . . . . ?
C1 N2 C6 C5 -147.67(9) . . . . ?
C10 O3 C19 O4 -0.03(17) . . . . ?
C10 O3 C19 C20 179.71(10) . . . . ?
C10 C9 C8 C7 -0.57(17) . . . . ?
C6 N2 C1 O1 -133.97(10) . . . . ?
C6 N2 C1 C2 111.84(10) . . . . ?
C18 C13 C3 N1 -154.48(9) . . . . ?
C18 C13 C3 C2 91.15(12) . . . . ?
C18 C13 C14 C15 -1.50(17) . . . . ?
C18 C17 C16 O5 -178.89(10) . . . . ?
C18 C17 C16 C15 -0.83(17) . . . . ?
C3 N1 N2 C1 43.90(10) . . . . ?
C3 N1 N2 C6 -96.00(9) . . . . ?
C3 N1 C4 C5 89.65(10) . . . . ?
C3 C13 C18 C17 -173.66(10) . . . . ?
C3 C13 C14 C15 173.43(10) . . . . ?
C16 C17 C18 C13 -0.20(17) . . . . ?
C14 C13 C18 C17 1.36(16) . . . . ?
C14 C13 C3 N1 30.62(14) . . . . ?
C14 C13 C3 C2 -83.75(12) . . . . ?
C2 C12 C11 C10 177.31(10) . . . . ?
C2 C12 C7 O1 1.66(12) . . . . ?
C2 C12 C7 C8 -177.82(10) . . . . ?
C4 N1 N2 C1 162.77(8) . . . . ?
C4 N1 N2 C6 22.88(11) . . . . ?
C4 N1 C3 C13 82.51(11) . . . . ?
C4 N1 C3 C2 -155.24(8) . . . . ?
C19 O3 C10 C11 -77.67(13) . . . . ?
C19 O3 C10 C9 106.28(12) . . . . ?
C21 O5 C16 C17 -6.63(17) . . . . ?
C21 O5 C16 C15 175.23(10) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 55.7 3.6 ?
2 0.000 0.500 0.000 55.7 3.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.918
_oxdiff_exptl_absorpt_empirical_full_min 0.524
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kks_3_2
_database_code_depnum_ccdc_archive 'CCDC 2076737'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(4aR,9bS,10S)-9b-nitro-3-oxo-10-phenyl-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_name_common            
'(4aR,9bS,10S)-9b-nitro-3-oxo-10-phenyl-2,3,4a,9b-tetrahydro-1H,10H-benzofuro[2,3-c]pyrazolo[1,2-a]pyrazol-8-yl acetate'
_chemical_formula_moiety         'C20 H17 N3 O6'
_chemical_formula_sum            'C20 H17 N3 O6'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         395.36
_exptl_crystal_recrystallization_method 'from acetonitrile'
_chemical_melting_point          467-468
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_oxdiff_formula         'C20 H17 N3 O6'
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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.08060(10)
_cell_length_b                   12.64680(10)
_cell_length_c                   17.15760(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.4370(10)
_cell_angle_gamma                90
_cell_volume                     3702.95(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1110
_cell_measurement_theta_min      4.3240
_shelx_estimated_absorpt_T_max   0.800
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 2 -1 0.1332
0 -8 3 0.1501
5 6 -6 0.1571
-5 -6 -6 0.1883
5 5 6 0.1844
3 2 10 0.2831
6 -6 -6 0.1369
-6 6 6 0.1225
10 -3 -2 0.1429
-11 2 3 0.1234
6 6 -5 0.1460
11 -1 0 0.1371
-11 -1 0 0.1250
-11 1 0 0.1221
5 7 -3 0.1513
2 7 5 0.1626
-4 6 -6 0.1956

_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.26
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
10.7677 1.9411 -0.7717 -0.9720 0.0240 0.2338
0.0781 -7.8577 3.2125 -0.0063 -0.0070 -1.0000
4.8578 5.9812 -6.0635 -0.4329 -0.2959 0.8515
-5.1942 -5.8258 -5.6330 0.4827 -0.7030 -0.5223
5.3727 5.4876 6.0485 -0.4992 0.7268 0.4717
2.9491 2.4114 10.0918 -0.2849 0.9585 0.0091
6.0248 -5.5163 -5.8568 -0.5297 -0.6898 -0.4935
-5.9835 5.5868 5.7706 0.5260 0.6850 0.5040
10.3562 -2.5667 -2.3617 -0.9287 -0.2755 -0.2482
-10.5184 2.0289 2.6432 0.9433 0.2800 0.1783
6.1879 6.0113 -4.6031 -0.5554 -0.1670 0.8146
11.0422 -0.5014 0.2618 -0.9966 0.0253 -0.0783
-10.9610 -1.2328 0.4715 0.9894 -0.0246 -0.1431
-11.0182 0.6901 -0.3415 0.9944 -0.0253 0.1023
5.0932 7.0085 -2.9390 -0.4602 0.0097 0.8878
2.0968 7.1385 4.9852 -0.2031 0.6888 0.6960
-4.2979 6.0750 -5.9321 0.3931 -0.2986 0.8697

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.373
_diffrn_reflns_theta_min         4.351
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_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    -74.00  34.00   1.00    1.00    --  -41.72  77.00-120.00  108
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.72 -38.00 120.00   99
  3  ω      7.00  33.00   1.00    1.00    --   41.72  84.00  -6.63   26
  4  ω    -21.00  74.00   1.00    1.00    --   41.72 -77.00-150.00   95
  5  ω      7.00  33.00   1.00    1.00    --   41.72  84.00  79.73   26
  6  ω     84.00 178.00   1.00    3.45    --  112.00  30.00 -30.00   94
  7  ω     39.00 138.00   1.00    3.45    --  112.00 -45.00  30.00   99
  8  ω     59.00 178.00   1.00    3.45    --  112.00  15.00 -60.00  119
  9  ω    104.00 178.00   1.00    3.45    --  112.00 111.00 120.00   74
 10  ω     30.00 106.00   1.00    3.45    --  112.00 -95.00   0.00   76
 11  ω     36.00 109.00   1.00    3.45    --  112.00-111.00 -60.00   73
 12  ω     84.00 178.00   1.00    3.45    --  112.00  30.00-150.00   94
 13  ω     36.00 145.00   1.00    3.45    --  112.00 -77.00 -90.00  109
 14  ω     36.00 145.00   1.00    3.45    --  112.00 -77.00  60.00  109
 15  ω     61.00 146.00   1.00    3.45    --  112.00 178.00 -60.00   85
 16  ω     36.00 145.00   1.00    3.45    --  112.00 -77.00 -60.00  109
 17  ω     36.00 109.00   1.00    3.45    --  112.00-111.00 150.00   73
 18  ω     36.00 109.00   1.00    3.45    --  112.00-111.00  60.00   73
 19  ω     36.00 109.00   1.00    3.45    --  112.00-111.00 -90.00   73
 20  ω    104.00 165.00   1.00    3.45    --  112.00 111.00  30.00   61
 21  ω     98.00 124.00   1.00    3.45    --  112.00-142.00-130.25   26
 22  ω     97.00 123.00   1.00    3.45    --  112.00 -61.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0902503000
_diffrn_orient_matrix_UB_12      -0.0007726000
_diffrn_orient_matrix_UB_13      -0.0016721000
_diffrn_orient_matrix_UB_21      0.0018920000
_diffrn_orient_matrix_UB_22      0.0359949000
_diffrn_orient_matrix_UB_23      0.0858256000
_diffrn_orient_matrix_UB_31      -0.0011740000
_diffrn_orient_matrix_UB_32      0.1163873000
_diffrn_orient_matrix_UB_33      -0.0265617000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3701
_reflns_number_total             3883
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00173(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+1.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C18(H18), C9(H9), C8(H8), C14(H14), C15(H15), C17(H17), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.26902(5) 0.09998(6) 0.71239(5) 0.0394(2) Uani 1 1 d . . . . .
O2 O 0.53118(5) 0.17078(9) 0.54541(5) 0.0523(2) Uani 1 1 d . . . . .
O5 O 0.30676(7) 0.36285(8) 0.83406(5) 0.0580(3) Uani 1 1 d . . . . .
O4 O 0.10004(6) 0.26620(9) 0.80277(6) 0.0607(3) Uani 1 1 d . . . . .
N2 N 0.19901(5) 0.29752(8) 0.63023(5) 0.0367(2) Uani 1 1 d . . . . .
N1 N 0.17668(5) 0.23787(8) 0.69787(5) 0.0373(2) Uani 1 1 d . . . . .
O3 O 0.61384(6) 0.12512(10) 0.64417(6) 0.0646(3) Uani 1 1 d . . . . .
N3 N 0.34926(6) 0.33830(8) 0.78139(6) 0.0409(2) Uani 1 1 d . . . . .
O6 O 0.41806(6) 0.35970(10) 0.77935(7) 0.0665(3) Uani 1 1 d . . . . .
C2 C 0.31058(6) 0.28196(8) 0.71184(6) 0.0325(2) Uani 1 1 d . . . . .
C13 C 0.30703(6) 0.42422(9) 0.60284(6) 0.0357(2) Uani 1 1 d . . . . .
C12 C 0.36453(6) 0.21243(9) 0.66864(6) 0.0342(2) Uani 1 1 d . . . . .
C3 C 0.26236(6) 0.36623(8) 0.66324(6) 0.0335(2) Uani 1 1 d . . . . .
H3 H 0.2400 0.4176 0.6988 0.040 Uiso 1 1 calc R U . . .
C1 C 0.24680(6) 0.20278(8) 0.73838(6) 0.0344(2) Uani 1 1 d . . . . .
H1 H 0.2417 0.2046 0.7950 0.041 Uiso 1 1 calc R U . . .
C7 C 0.33534(6) 0.11057(9) 0.67087(6) 0.0359(2) Uani 1 1 d . . . . .
C11 C 0.43151(6) 0.23438(10) 0.62834(6) 0.0389(2) Uani 1 1 d . . . . .
H11 H 0.4519 0.3024 0.6261 0.047 Uiso 1 1 calc R U . . .
C10 C 0.46639(7) 0.15041(10) 0.59173(7) 0.0423(3) Uani 1 1 d . . . . .
C18 C 0.35378(8) 0.50931(10) 0.62611(7) 0.0446(3) Uani 1 1 d . . . . .
H18 H 0.3549 0.5315 0.6778 0.054 Uiso 1 1 calc R U . . .
C9 C 0.43733(8) 0.04859(10) 0.59418(7) 0.0460(3) Uani 1 1 d . . . . .
H9 H 0.4628 -0.0056 0.5688 0.055 Uiso 1 1 calc R U . . .
C8 C 0.37039(8) 0.02679(9) 0.63430(7) 0.0441(3) Uani 1 1 d . . . . .
H8 H 0.3500 -0.0413 0.6365 0.053 Uiso 1 1 calc R U . . .
C6 C 0.11720(7) 0.28783(10) 0.73697(8) 0.0443(3) Uani 1 1 d . . . . .
C19 C 0.60349(7) 0.15447(10) 0.57869(8) 0.0442(3) Uani 1 1 d . . . . .
C14 C 0.30418(8) 0.39441(10) 0.52482(7) 0.0462(3) Uani 1 1 d . . . . .
H14 H 0.2726 0.3382 0.5083 0.055 Uiso 1 1 calc R U . . .
C4 C 0.12543(7) 0.35407(11) 0.60727(8) 0.0493(3) Uani 1 1 d . . . . .
H4A H 0.0946 0.3130 0.5693 0.059 Uiso 1 1 calc R U . . .
H4B H 0.1370 0.4222 0.5845 0.059 Uiso 1 1 calc R U . . .
C5 C 0.08089(8) 0.36831(12) 0.68188(9) 0.0531(3) Uani 1 1 d . . . . .
H5A H 0.0877 0.4393 0.7025 0.064 Uiso 1 1 calc R U . . .
H5B H 0.0254 0.3547 0.6725 0.064 Uiso 1 1 calc R U . . .
C15 C 0.34823(9) 0.44807(12) 0.47165(8) 0.0558(3) Uani 1 1 d . . . . .
H15 H 0.3456 0.4281 0.4194 0.067 Uiso 1 1 calc R U . . .
C17 C 0.39873(9) 0.56138(11) 0.57282(9) 0.0555(3) Uani 1 1 d . . . . .
H17 H 0.4309 0.6171 0.5891 0.067 Uiso 1 1 calc R U . . .
C16 C 0.39580(9) 0.53073(12) 0.49563(8) 0.0568(3) Uani 1 1 d . . . . .
H16 H 0.4259 0.5658 0.4599 0.068 Uiso 1 1 calc R U . . .
C20 C 0.66586(9) 0.17868(14) 0.52317(10) 0.0617(4) Uani 1 1 d . . . . .
H20A H 0.6425 0.1894 0.4719 0.093 Uiso 1 1 calc R U . . .
H20B H 0.7020 0.1206 0.5221 0.093 Uiso 1 1 calc R U . . .
H20C H 0.6933 0.2416 0.5398 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4309(13) . ?
O1 C7 1.3702(13) . ?
O2 C10 1.4133(14) . ?
O2 C19 1.3544(16) . ?
O5 N3 1.2230(14) . ?
O4 C6 1.2098(15) . ?
N2 N1 1.4489(13) . ?
N2 C3 1.4815(14) . ?
N2 C4 1.4846(15) . ?
N1 C1 1.4297(14) . ?
N1 C6 1.3925(15) . ?
O3 C19 1.1893(16) . ?
N3 O6 1.2079(15) . ?
N3 C2 1.5169(13) . ?
C2 C12 1.4932(14) . ?
C2 C3 1.5655(14) . ?
C2 C1 1.5618(15) . ?
C13 C3 1.5038(15) . ?
C13 C18 1.3884(16) . ?
C13 C14 1.3896(16) . ?
C12 C7 1.3824(16) . ?
C12 C11 1.3898(15) . ?
C3 H3 0.9800 . ?
C1 H1 0.9800 . ?
C7 C8 1.3808(16) . ?
C11 H11 0.9300 . ?
C11 C10 1.3817(17) . ?
C10 C9 1.3814(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.3851(18) . ?
C9 H9 0.9300 . ?
C9 C8 1.3871(18) . ?
C8 H8 0.9300 . ?
C6 C5 1.5047(17) . ?
C19 C20 1.4907(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3846(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5273(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C16 1.376(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(2) . ?
C16 H16 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C7 O1 C1 108.01(8) . . ?
C19 O2 C10 117.19(9) . . ?
N1 N2 C3 102.24(8) . . ?
N1 N2 C4 102.39(9) . . ?
C3 N2 C4 114.53(10) . . ?
C1 N1 N2 107.90(8) . . ?
C6 N1 N2 111.84(9) . . ?
C6 N1 C1 121.32(9) . . ?
O5 N3 C2 116.63(10) . . ?
O6 N3 O5 124.97(11) . . ?
O6 N3 C2 118.31(10) . . ?
N3 C2 C3 107.51(8) . . ?
N3 C2 C1 110.96(8) . . ?
C12 C2 N3 114.19(9) . . ?
C12 C2 C3 117.28(8) . . ?
C12 C2 C1 102.71(8) . . ?
C1 C2 C3 103.54(8) . . ?
C18 C13 C3 118.84(10) . . ?
C18 C13 C14 118.91(11) . . ?
C14 C13 C3 122.24(10) . . ?
C7 C12 C2 107.71(9) . . ?
C7 C12 C11 120.36(10) . . ?
C11 C12 C2 131.89(10) . . ?
N2 C3 C2 99.41(8) . . ?
N2 C3 C13 113.97(8) . . ?
N2 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C13 C3 C2 115.35(9) . . ?
C13 C3 H3 109.2 . . ?
O1 C1 C2 107.11(8) . . ?
O1 C1 H1 111.5 . . ?
N1 C1 O1 111.00(9) . . ?
N1 C1 C2 103.86(8) . . ?
N1 C1 H1 111.5 . . ?
C2 C1 H1 111.5 . . ?
O1 C7 C12 114.37(9) . . ?
O1 C7 C8 123.04(11) . . ?
C8 C7 C12 122.59(11) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 C12 116.91(11) . . ?
C10 C11 H11 121.5 . . ?
C11 C10 O2 118.60(12) . . ?
C9 C10 O2 118.55(11) . . ?
C9 C10 C11 122.70(11) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.45(12) . . ?
C17 C18 H18 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.34(11) . . ?
C8 C9 H9 119.8 . . ?
C7 C8 C9 117.10(11) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
O4 C6 N1 123.90(11) . . ?
O4 C6 C5 129.00(12) . . ?
N1 C6 C5 107.09(10) . . ?
O2 C19 C20 111.28(12) . . ?
O3 C19 O2 122.82(12) . . ?
O3 C19 C20 125.89(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.26(12) . . ?
C15 C14 H14 119.9 . . ?
N2 C4 H4A 110.5 . . ?
N2 C4 H4B 110.5 . . ?
N2 C4 C5 106.30(10) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C6 C5 C4 103.89(10) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.39(13) . . ?
C16 C15 H15 119.8 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.13(13) . . ?
C16 C17 H17 119.9 . . ?
C15 C16 C17 119.84(12) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 C7 C8 C9 179.98(10) . . . . ?
O2 C10 C9 C8 -175.29(10) . . . . ?
O5 N3 C2 C12 -153.66(10) . . . . ?
O5 N3 C2 C3 74.38(12) . . . . ?
O5 N3 C2 C1 -38.17(13) . . . . ?
O4 C6 C5 C4 -177.34(15) . . . . ?
N2 N1 C1 O1 -92.00(10) . . . . ?
N2 N1 C1 C2 22.79(11) . . . . ?
N2 N1 C6 O4 -163.91(13) . . . . ?
N2 N1 C6 C5 16.85(13) . . . . ?
N2 C4 C5 C6 -18.89(14) . . . . ?
N1 N2 C3 C2 46.37(9) . . . . ?
N1 N2 C3 C13 169.65(8) . . . . ?
N1 N2 C4 C5 28.00(13) . . . . ?
N1 C6 C5 C4 1.85(14) . . . . ?
N3 C2 C12 C7 120.18(10) . . . . ?
N3 C2 C12 C11 -62.24(15) . . . . ?
N3 C2 C3 N2 -149.87(8) . . . . ?
N3 C2 C3 C13 87.84(10) . . . . ?
N3 C2 C1 O1 -120.60(9) . . . . ?
N3 C2 C1 N1 121.88(9) . . . . ?
O6 N3 C2 C12 29.58(15) . . . . ?
O6 N3 C2 C3 -102.38(12) . . . . ?
O6 N3 C2 C1 145.07(11) . . . . ?
C2 C12 C7 O1 -1.94(12) . . . . ?
C2 C12 C7 C8 178.15(10) . . . . ?
C2 C12 C11 C10 -177.47(11) . . . . ?
C13 C18 C17 C16 1.7(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C12 C2 C3 N2 79.88(10) . . . . ?
C12 C2 C3 C13 -42.42(13) . . . . ?
C12 C2 C1 O1 1.82(10) . . . . ?
C12 C2 C1 N1 -115.70(9) . . . . ?
C12 C7 C8 C9 -0.12(17) . . . . ?
C12 C11 C10 O2 175.40(10) . . . . ?
C12 C11 C10 C9 -0.06(17) . . . . ?
C3 N2 N1 C1 -45.47(10) . . . . ?
C3 N2 N1 C6 90.42(10) . . . . ?
C3 N2 C4 C5 -81.81(12) . . . . ?
C3 C2 C12 C7 -112.76(10) . . . . ?
C3 C2 C12 C11 64.83(15) . . . . ?
C3 C2 C1 O1 124.34(8) . . . . ?
C3 C2 C1 N1 6.82(10) . . . . ?
C3 C13 C18 C17 176.85(12) . . . . ?
C3 C13 C14 C15 -177.96(12) . . . . ?
C1 O1 C7 C12 3.19(12) . . . . ?
C1 O1 C7 C8 -176.90(10) . . . . ?
C1 N1 C6 O4 -34.75(19) . . . . ?
C1 N1 C6 C5 146.01(11) . . . . ?
C1 C2 C12 C7 -0.03(11) . . . . ?
C1 C2 C12 C11 177.55(11) . . . . ?
C1 C2 C3 N2 -32.37(9) . . . . ?
C1 C2 C3 C13 -154.67(9) . . . . ?
C7 O1 C1 N1 109.76(10) . . . . ?
C7 O1 C1 C2 -2.99(11) . . . . ?
C7 C12 C11 C10 -0.14(16) . . . . ?
C11 C12 C7 O1 -179.85(9) . . . . ?
C11 C12 C7 C8 0.23(17) . . . . ?
C11 C10 C9 C8 0.17(19) . . . . ?
C10 O2 C19 O3 -0.60(19) . . . . ?
C10 O2 C19 C20 179.79(12) . . . . ?
C10 C9 C8 C7 -0.08(18) . . . . ?
C18 C13 C3 N2 164.24(10) . . . . ?
C18 C13 C3 C2 -81.64(13) . . . . ?
C18 C13 C14 C15 0.89(19) . . . . ?
C18 C17 C16 C15 -0.1(2) . . . . ?
C6 N1 C1 O1 137.14(10) . . . . ?
C6 N1 C1 C2 -108.07(11) . . . . ?
C19 O2 C10 C11 98.08(13) . . . . ?
C19 O2 C10 C9 -86.28(14) . . . . ?
C14 C13 C3 N2 -16.91(15) . . . . ?
C14 C13 C3 C2 97.22(13) . . . . ?
C14 C13 C18 C17 -2.04(19) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C4 N2 N1 C1 -164.32(9) . . . . ?
C4 N2 N1 C6 -28.43(12) . . . . ?
C4 N2 C3 C2 156.27(9) . . . . ?
C4 N2 C3 C13 -80.46(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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kor_9_100_1
_database_code_depnum_ccdc_archive 'CCDC 2077063'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(7aR,13R,13aS)-13-(2-chlorophenyl)-13a-nitro-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one
_chemical_name_common            
(7aR,13R,13aS)-13-(2-chlorophenyl)-13a-nitro-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one
_chemical_formula_moiety         'C23 H18 Cl N3 O4'
_chemical_formula_sum            'C23 H18 Cl N3 O4'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         435.85
_exptl_crystal_recrystallization_method 'from acetonitrile'
_chemical_melting_point          470-471
_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C23 H18 Cl N3 O4'
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'
Cl Cl 0.3639 0.7018 '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                   7.5805(2)
_cell_length_b                   8.9682(3)
_cell_length_c                   15.1658(5)
_cell_angle_alpha                92.886(3)
_cell_angle_beta                 97.851(3)
_cell_angle_gamma                102.333(3)
_cell_volume                     994.41(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15263
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1400
_cell_measurement_theta_min      5.0530
_shelx_estimated_absorpt_T_max   0.513
_shelx_estimated_absorpt_T_min   0.387
_exptl_absorpt_coefficient_mu    2.022
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             452
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -4 0.2103
1 -2 -9 0.2037
-5 0 3 0.1700
-5 0 -1 0.1997
5 0 2 0.1900
-5 0 3 0.1761
1 4 -7 0.1995
-3 -3 1 0.1858
1 -3 8 0.2240
-2 0 10 0.2003
1 2 8 0.1897
0 6 -1 0.1908
0 -6 2 0.2219
-4 4 4 0.2660
5 -2 0 0.2223
4 2 -1 0.2082
3 2 6 0.1995
3 -1 -8 0.2319
-1 -4 -3 0.1862
-1 -2 -8 0.1908
-1 0 10 0.1886
-4 0 -5 0.2193
-1 -4 7 0.2280
0 -5 -5 0.1864
0 6 -1 0.1911
-2 6 2 0.2626
5 0 -2 0.1973

_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.381
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
4.6689 -1.0184 -4.3470 -0.9220 -0.0743 -0.3800
0.5672 -2.3237 -8.7512 -0.3666 0.8810 -0.2991
-4.6790 -0.3704 2.9014 0.8190 0.3412 0.4613
-4.5757 -0.3030 -1.1015 0.7456 0.6385 0.1908
4.5694 0.0509 1.5377 -0.7531 -0.6448 -0.1309
-4.7600 -0.0960 2.5346 0.8438 0.3495 0.4074
0.8795 4.1278 -6.8650 -0.0056 -0.0076 -1.0000
-3.4854 -3.0973 0.5967 0.4179 0.6858 0.5959
1.2853 -3.0678 8.1593 -0.2807 -0.4557 0.8447
-1.8816 0.1097 9.5203 0.4697 -0.5512 0.6896
0.9939 2.1262 7.9997 0.0774 -0.9769 0.1993
0.4455 5.5509 -1.0147 0.2411 -0.5761 -0.7810
0.3312 -5.7070 1.9969 -0.3681 0.4275 0.8257
-4.1121 3.5533 3.9303 0.9725 -0.2325 0.0090
4.8435 -1.6935 0.2479 -0.9235 -0.3835 -0.0090
4.3630 1.5122 -1.1064 -0.6700 -0.5719 -0.4734
2.5857 2.0349 5.7889 -0.2325 -0.9725 -0.0091
3.0137 -0.8880 -8.4809 -0.6938 0.4257 -0.5808
-1.4342 -4.4785 -3.1678 -0.0708 0.9016 0.4267
-0.9778 -2.0770 -8.0611 -0.0781 0.9745 -0.2101
-0.8018 0.1687 9.8094 0.2935 -0.7028 0.6480
-3.5315 -0.0976 -5.4472 0.5148 0.8413 -0.1650
-0.8561 -4.0856 6.9650 0.0056 -0.0076 1.0000
0.0615 -4.7738 -4.6672 -0.3660 0.8829 0.2942
0.4258 5.5546 -0.5677 0.2513 -0.6096 -0.7518
-2.3219 5.5143 1.5222 0.7487 -0.4591 -0.4783
4.8268 -0.1856 -2.1042 -0.8656 -0.3603 -0.3478

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7849
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.593
_diffrn_reflns_theta_min         2.951
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 150.00  100
  2  ω    -69.00  32.00   1.00    1.00    --  -41.35  57.00 -60.00  101
  3  ω    -87.00  -6.00   1.00    1.00    --  -41.35 125.00 -30.00   81
  4  ω      8.00  42.00   1.00    1.00    --   41.35  81.00 146.57   34
  5  ω     17.00 116.00   1.00    1.00    --   41.35  38.00  90.00   99
  6  ω      6.00  82.00   1.00    1.00    --   41.35 -99.00   0.00   76
  7  ω     36.00 109.00   1.00    1.00    --  112.00-111.00  30.00   73
  8  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00-180.00   99
  9  ω     36.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   73
 10  ω     61.00 146.00   1.00    1.00    --  112.00 178.00-180.00   85
 11  ω     59.00 178.00   1.00    1.00    --  112.00  15.00 -90.00  119
 12  ω     36.00 109.00   1.00    1.00    --  112.00-111.00-180.00   73
 13  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00-120.00   76
 14  ω     36.00 109.00   1.00    1.00    --  112.00-111.00-120.00   73
 15  ω     36.00 109.00   1.00    1.00    --  112.00-111.00  60.00   73
 16  ω     36.00 109.00   1.00    1.00    --  112.00-111.00-150.00   73
 17  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00 150.00   76
 18  ω     29.00 178.00   1.00    1.00    --  112.00   7.00 -86.16  149
 19  ω    104.00 178.00   1.00    1.00    --  112.00 111.00   0.00   74
 20  ω     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 21  ω     36.00 109.00   1.00    1.00    --  112.00-111.00 120.00   73
 22  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 120.00   95
 23  ω    104.00 178.00   1.00    1.00    --  112.00 111.00-180.00   74
 24  ω    104.00 178.00   1.00    1.00    --  112.00 111.00 150.00   74
 25  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00-150.00   76
 26  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00 -60.00   76
 27  ω     61.00 146.00   1.00    1.00    --  112.00 178.00-120.00   85
 28  ω     36.00 140.00   1.00    1.00    --  112.00 -30.00-180.00  104
 29  ω     59.00 178.00   1.00    1.00    --  112.00  15.00 -30.00  119
 30  ω    103.00 178.00   1.00    1.00    --  112.00  77.00 150.00   75
 31  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00  30.00  101
 32  ω     30.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   76
 33  ω     36.00 109.00   1.00    1.00    --  112.00-111.00 150.00   73
 34  ω     36.00 140.00   1.00    1.00    --  112.00 -30.00  90.00  104
 35  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00 -60.00  109
 36  ω     30.00 165.00   1.00    1.00    --  112.00 -15.00   0.00  135
 37  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 -30.00   95
 38  ω     89.00 114.00   1.00    1.00    --  112.00 -30.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1705047000
_diffrn_orient_matrix_UB_12      0.0598451000
_diffrn_orient_matrix_UB_13      0.0149540000
_diffrn_orient_matrix_UB_21      -0.1132981000
_diffrn_orient_matrix_UB_22      -0.1091370000
_diffrn_orient_matrix_UB_23      -0.0790321000
_diffrn_orient_matrix_UB_31      -0.0488703000
_diffrn_orient_matrix_UB_32      -0.1250415000
_diffrn_orient_matrix_UB_33      0.0642138000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7728
_reflns_number_total             7849
_reflns_odcompleteness_completeness 98.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         7849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.069
_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)+(0.1682P)²+0.3689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2129
_refine_ls_wR_factor_ref         0.2134
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.3908(18)
 0.6092(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C3(H3), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C23(H23), C11(H11), C22(H22), C10(H10), C15(H15),
 C21(H21), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.58111(8) 0.19227(7) 0.31914(4) 0.0256(2) Uani 1 1 d . . . . .
O1 O 1.1049(2) 0.67963(19) 0.21534(12) 0.0193(4) Uani 1 1 d . . . . .
O3 O 0.7963(2) 0.4717(2) -0.00768(12) 0.0208(4) Uani 1 1 d . . . . .
O2 O 0.8824(3) 0.9426(2) 0.20809(15) 0.0271(5) Uani 1 1 d . . . . .
O4 O 0.8411(3) 0.2526(2) 0.03239(13) 0.0241(4) Uani 1 1 d . . . . .
N2 N 0.7947(3) 0.6816(2) 0.17823(14) 0.0178(4) Uani 1 1 d . . . . .
N3 N 0.8346(3) 0.3855(2) 0.04893(14) 0.0172(4) Uani 1 1 d . . . . .
N1 N 0.6272(3) 0.5680(2) 0.15423(14) 0.0159(4) Uani 1 1 d . . . . .
C18 C 0.5311(3) 0.2913(3) 0.15162(16) 0.0157(5) Uani 1 1 d . . . . .
C20 C 0.3103(3) 0.0699(3) 0.18588(18) 0.0191(5) Uani 1 1 d . . . . .
H20 H 0.2673 0.0007 0.2277 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7668(3) 0.8231(3) 0.19832(17) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.8711(3) 0.4466(3) 0.14691(15) 0.0156(5) Uani 1 1 d . . . . .
C3 C 0.6843(3) 0.4290(3) 0.18207(15) 0.0148(5) Uani 1 1 d . . . . .
H3 H 0.7087 0.4368 0.2488 0.018 Uiso 1 1 calc R U . . .
C7 C 1.0011(3) 0.3620(3) 0.19898(17) 0.0174(5) Uani 1 1 d . . . . .
H7A H 0.9347 0.2571 0.2070 0.021 Uiso 1 1 calc R U . . .
H7B H 1.1020 0.3541 0.1651 0.021 Uiso 1 1 calc R U . . .
C19 C 0.4666(3) 0.1850(3) 0.21060(16) 0.0171(5) Uani 1 1 d . . . . .
C16 C 1.2041(4) 0.6978(3) 0.37162(19) 0.0276(6) Uani 1 1 d . . . . .
H16 H 1.2301 0.8063 0.3719 0.033 Uiso 1 1 calc R U . . .
C23 C 0.4340(3) 0.2762(3) 0.06484(16) 0.0190(5) Uani 1 1 d . . . . .
H23 H 0.4735 0.3476 0.0235 0.023 Uiso 1 1 calc R U . . .
C1 C 0.9467(3) 0.6239(3) 0.15288(16) 0.0164(5) Uani 1 1 d . . . . .
H1 H 0.9696 0.6561 0.0925 0.020 Uiso 1 1 calc R U . . .
C6 C 0.5031(3) 0.6254(3) 0.20792(17) 0.0189(5) Uani 1 1 d . . . . .
H6A H 0.5202 0.5959 0.2700 0.023 Uiso 1 1 calc R U . . .
H6B H 0.3736 0.5873 0.1810 0.023 Uiso 1 1 calc R U . . .
C8 C 1.0779(3) 0.4478(3) 0.28929(17) 0.0188(5) Uani 1 1 d . . . . .
C11 C 1.1357(4) 0.1477(4) 0.4473(2) 0.0320(6) Uani 1 1 d . . . . .
H11 H 1.1135 0.0394 0.4473 0.038 Uiso 1 1 calc R U . . .
C17 C 1.1222(3) 0.6048(3) 0.29278(17) 0.0188(5) Uani 1 1 d . . . . .
C22 C 0.2812(3) 0.1586(3) 0.03850(18) 0.0220(5) Uani 1 1 d . . . . .
H22 H 0.2198 0.1474 -0.0212 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5640(3) 0.7986(3) 0.20429(18) 0.0222(5) Uani 1 1 d . . . . .
H5A H 0.4974 0.8334 0.1513 0.027 Uiso 1 1 calc R U . . .
H5B H 0.5437 0.8542 0.2587 0.027 Uiso 1 1 calc R U . . .
C10 C 1.0859(4) 0.2129(3) 0.37065(18) 0.0244(5) Uani 1 1 d . . . . .
H10 H 1.0283 0.1490 0.3183 0.029 Uiso 1 1 calc R U . . .
C9 C 1.1192(3) 0.3750(3) 0.36838(17) 0.0216(5) Uani 1 1 d . . . . .
C15 C 1.2453(5) 0.6291(4) 0.4474(2) 0.0352(7) Uani 1 1 d . . . . .
H15 H 1.3019 0.6908 0.5007 0.042 Uiso 1 1 calc R U . . .
C14 C 1.2058(4) 0.4674(4) 0.44864(19) 0.0297(6) Uani 1 1 d . . . . .
C21 C 0.2177(3) 0.0572(3) 0.09939(18) 0.0207(5) Uani 1 1 d . . . . .
H21 H 0.1105 -0.0211 0.0818 0.025 Uiso 1 1 calc R U . . .
C13 C 1.2532(5) 0.3954(4) 0.5265(2) 0.0422(8) Uani 1 1 d . . . . .
H13 H 1.3095 0.4568 0.5800 0.051 Uiso 1 1 calc R U . . .
C12 C 1.2198(5) 0.2400(5) 0.5266(2) 0.0418(8) Uani 1 1 d . . . . .
H12 H 1.2528 0.1939 0.5796 0.050 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
Cl1 C19 1.744(3) . ?
O1 C1 1.404(3) . ?
O1 C17 1.386(3) . ?
O3 N3 1.231(3) . ?
O2 C4 1.219(3) . ?
O4 N3 1.218(3) . ?
N2 N1 1.438(2) . ?
N2 C4 1.357(3) . ?
N2 C1 1.449(3) . ?
N3 C2 1.525(3) . ?
N1 C3 1.467(3) . ?
N1 C6 1.479(3) . ?
C18 C3 1.507(3) . ?
C18 C19 1.398(3) . ?
C18 C23 1.402(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.388(3) . ?
C20 C21 1.388(4) . ?
C4 C5 1.522(3) . ?
C2 C3 1.561(3) . ?
C2 C7 1.529(3) . ?
C2 C1 1.564(3) . ?
C3 H3 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.410(3) . ?
C16 C15 1.362(4) . ?
C23 H23 0.9500 . ?
C23 C22 1.387(3) . ?
C1 H1 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.529(3) . ?
C8 C17 1.372(3) . ?
C8 C9 1.423(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.371(4) . ?
C11 C12 1.415(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.389(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.425(4) . ?
C9 C14 1.431(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.418(4) . ?
C14 C13 1.415(4) . ?
C21 H21 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.363(5) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O1 C1 117.05(18) . . ?
N1 N2 C1 110.33(17) . . ?
C4 N2 N1 112.78(19) . . ?
C4 N2 C1 134.6(2) . . ?
O3 N3 C2 118.16(19) . . ?
O4 N3 O3 124.5(2) . . ?
O4 N3 C2 117.3(2) . . ?
N2 N1 C3 101.39(16) . . ?
N2 N1 C6 102.33(17) . . ?
C3 N1 C6 116.17(19) . . ?
C19 C18 C3 121.8(2) . . ?
C19 C18 C23 117.6(2) . . ?
C23 C18 C3 120.1(2) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C21 C20 C19 119.2(2) . . ?
O2 C4 N2 126.0(2) . . ?
O2 C4 C5 128.7(2) . . ?
N2 C4 C5 105.3(2) . . ?
N3 C2 C3 108.45(17) . . ?
N3 C2 C7 109.13(18) . . ?
N3 C2 C1 108.66(19) . . ?
C3 C2 C1 103.76(17) . . ?
C7 C2 C3 113.28(19) . . ?
C7 C2 C1 113.31(18) . . ?
N1 C3 C18 109.50(18) . . ?
N1 C3 C2 101.75(18) . . ?
N1 C3 H3 108.0 . . ?
C18 C3 C2 120.87(19) . . ?
C18 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C2 C7 H7A 109.7 . . ?
C2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C2 109.68(18) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C18 C19 Cl1 120.84(18) . . ?
C20 C19 Cl1 117.2(2) . . ?
C20 C19 C18 121.9(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.6(3) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.5 . . ?
O1 C1 N2 110.61(19) . . ?
O1 C1 C2 115.12(19) . . ?
O1 C1 H1 109.6 . . ?
N2 C1 C2 102.17(18) . . ?
N2 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
N1 C6 H6A 111.4 . . ?
N1 C6 H6B 111.4 . . ?
N1 C6 C5 101.77(19) . . ?
H6A C6 H6B 109.3 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C17 C8 C7 117.3(2) . . ?
C17 C8 C9 118.7(2) . . ?
C9 C8 C7 123.8(2) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
O1 C17 C16 116.1(2) . . ?
C8 C17 O1 120.5(2) . . ?
C8 C17 C16 123.0(2) . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.1(2) . . ?
C21 C22 H22 120.0 . . ?
C4 C5 C6 103.66(18) . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C8 C9 C10 122.9(2) . . ?
C8 C9 C14 119.1(2) . . ?
C10 C9 C14 117.9(3) . . ?
C16 C15 H15 119.2 . . ?
C16 C15 C14 121.5(2) . . ?
C14 C15 H15 119.2 . . ?
C15 C14 C9 119.0(3) . . ?
C13 C14 C9 119.3(3) . . ?
C13 C14 C15 121.7(3) . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?

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
O3 N3 C2 C3 83.9(2) . . . . ?
O3 N3 C2 C7 -152.2(2) . . . . ?
O3 N3 C2 C1 -28.2(3) . . . . ?
O2 C4 C5 C6 -167.1(3) . . . . ?
O4 N3 C2 C3 -94.3(2) . . . . ?
O4 N3 C2 C7 29.6(3) . . . . ?
O4 N3 C2 C1 153.6(2) . . . . ?
N2 N1 C3 C18 -172.92(18) . . . . ?
N2 N1 C3 C2 -43.9(2) . . . . ?
N2 N1 C6 C5 36.8(2) . . . . ?
N2 C4 C5 C6 13.7(3) . . . . ?
N3 C2 C3 N1 -84.3(2) . . . . ?
N3 C2 C3 C18 37.2(3) . . . . ?
N3 C2 C7 C8 165.05(19) . . . . ?
N3 C2 C1 O1 -131.2(2) . . . . ?
N3 C2 C1 N2 108.9(2) . . . . ?
N1 N2 C4 O2 -168.7(3) . . . . ?
N1 N2 C4 C5 10.5(3) . . . . ?
N1 N2 C1 O1 -145.04(19) . . . . ?
N1 N2 C1 C2 -22.0(2) . . . . ?
N1 C6 C5 C4 -31.3(2) . . . . ?
C18 C23 C22 C21 2.6(4) . . . . ?
C4 N2 N1 C3 -151.4(2) . . . . ?
C4 N2 N1 C6 -31.1(3) . . . . ?
C4 N2 C1 O1 53.9(4) . . . . ?
C4 N2 C1 C2 177.0(3) . . . . ?
C2 C7 C8 C17 -39.2(3) . . . . ?
C2 C7 C8 C9 145.8(2) . . . . ?
C3 N1 C6 C5 146.21(19) . . . . ?
C3 C18 C19 Cl1 -8.8(3) . . . . ?
C3 C18 C19 C20 171.1(2) . . . . ?
C3 C18 C23 C22 -173.5(2) . . . . ?
C3 C2 C7 C8 -74.0(2) . . . . ?
C3 C2 C1 O1 113.5(2) . . . . ?
C3 C2 C1 N2 -6.4(2) . . . . ?
C7 C2 C3 N1 154.43(18) . . . . ?
C7 C2 C3 C18 -84.1(2) . . . . ?
C7 C2 C1 O1 -9.7(3) . . . . ?
C7 C2 C1 N2 -129.6(2) . . . . ?
C7 C8 C17 O1 -3.2(3) . . . . ?
C7 C8 C17 C16 -176.4(2) . . . . ?
C7 C8 C9 C10 -2.2(4) . . . . ?
C7 C8 C9 C14 174.8(2) . . . . ?
C19 C18 C3 N1 -127.7(2) . . . . ?
C19 C18 C3 C2 114.7(2) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C16 C15 C14 C9 -0.5(5) . . . . ?
C16 C15 C14 C13 178.1(3) . . . . ?
C23 C18 C3 N1 44.6(3) . . . . ?
C23 C18 C3 C2 -73.0(3) . . . . ?
C23 C18 C19 Cl1 178.66(17) . . . . ?
C23 C18 C19 C20 -1.4(3) . . . . ?
C23 C22 C21 C20 -2.2(4) . . . . ?
C1 O1 C17 C16 -143.5(2) . . . . ?
C1 O1 C17 C8 42.8(3) . . . . ?
C1 N2 N1 C3 43.2(2) . . . . ?
C1 N2 N1 C6 163.5(2) . . . . ?
C1 N2 C4 O2 -8.1(5) . . . . ?
C1 N2 C4 C5 171.2(3) . . . . ?
C1 C2 C3 N1 31.1(2) . . . . ?
C1 C2 C3 C18 152.6(2) . . . . ?
C1 C2 C7 C8 43.8(3) . . . . ?
C6 N1 C3 C18 77.1(2) . . . . ?
C6 N1 C3 C2 -153.88(18) . . . . ?
C8 C9 C14 C15 1.0(4) . . . . ?
C8 C9 C14 C13 -177.7(3) . . . . ?
C11 C10 C9 C8 176.9(2) . . . . ?
C11 C10 C9 C14 -0.1(4) . . . . ?
C17 O1 C1 N2 81.2(2) . . . . ?
C17 O1 C1 C2 -33.9(3) . . . . ?
C17 C16 C15 C14 -0.7(5) . . . . ?
C17 C8 C9 C10 -177.2(2) . . . . ?
C17 C8 C9 C14 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C10 C9 C14 C15 178.2(3) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C9 C8 C17 O1 172.2(2) . . . . ?
C9 C8 C17 C16 -1.1(4) . . . . ?
C9 C14 C13 C12 0.7(6) . . . . ?
C15 C16 C17 O1 -171.9(2) . . . . ?
C15 C16 C17 C8 1.6(4) . . . . ?
C15 C14 C13 C12 -178.0(3) . . . . ?
C14 C13 C12 C11 -0.1(6) . . . . ?
C21 C20 C19 Cl1 -178.25(18) . . . . ?
C21 C20 C19 C18 1.8(4) . . . . ?
C12 C11 C10 C9 0.7(5) . . . . ?

_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.761
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3908(18)
2 0.6092(18)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_kor_14p1
_database_code_depnum_ccdc_archive 'CCDC 2083590'
loop_
_audit_author_name
_audit_author_address
'Oleg Demidov'
;North Caucasus Federal University, Department of Chemistry
Russia
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-05-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
10-methyl-13a-nitro-13-(pyridin-2-yl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one
_chemical_name_common            
10-methyl-13a-nitro-13-(pyridin-2-yl)-7a,10,11,13a-tetrahydro-9H,13H,14H-benzo[5,6]chromeno[2,3-c]pyrazolo[1,2-a]pyrazol-9-one
_chemical_formula_moiety         'C23 H20 N4 O4'
_chemical_formula_sum            'C23 H20 N4 O4'
_chemical_compound_source        'Samara, Russia'
_chemical_formula_weight         416.43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33
_chemical_absolute_configuration .
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_chemical_melting_point          448-449
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      99.99(10)
_chemical_oxdiff_formula         'C23 H20 N4 O4'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.82982(8)
_cell_length_b                   5.65071(4)
_cell_length_c                   41.3175(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3929.32(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    75817
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2660
_cell_measurement_theta_min      4.2840
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
11 0 2 0.0901
0 -3 10 0.1773
0 0 -27 0.0265
-1 0 27 0.0198
1 0 -27 0.0198
1 3 -10 0.2389
-11 0 -2 0.1172

_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.04
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
10.8977 0.0330 2.1121 0.9454 -0.0246 -0.3250
-0.0351 -3.4143 9.8359 -0.3089 0.0056 -0.9511
-0.4037 -0.1221 -26.7981 0.0228 0.9363 0.3504
-0.8400 0.1995 26.7108 -0.1244 -0.9470 -0.2961
0.8400 -0.1995 -26.7108 0.1244 0.9470 0.2961
0.7952 3.4123 -9.6762 0.3744 -0.0073 0.9272
-10.8979 -0.1811 -1.6480 -0.9588 0.0235 0.2832

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            140500
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.592
_diffrn_reflns_theta_min         2.139
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  31.00   0.75    1.23    --   34.00  87.00  55.69   44
  2  ω      1.00  28.00   0.75    1.23    --   38.00  90.00-130.61   36
  3  ω    -87.00  -6.00   0.75    1.23    --  -41.35 125.00-180.00  108
  4  ω   -113.00 -14.00   0.75    1.23    --  -41.35 -57.00-180.00  132
  5  ω   -116.00 -17.00   0.75    1.23    --  -41.35 -38.00   0.00  132
  6  ω   -116.00 -17.00   0.75    1.23    --  -41.35 -38.00 -90.00  132
  7  ω    -33.00  66.00   0.75    1.23    --   41.35 -38.00 -90.00  132
  8  ω     27.00  96.00   0.75    1.23    --   41.35-125.00  60.00   92
  9  ω      6.00  81.00   0.75    1.23    --   41.35 -99.00 150.00  100
 10  ω      6.00  31.50   0.75    1.23    --   41.35  85.00 -71.69   34
 11  ω      8.00  33.50   0.75    1.23    --   42.00  83.00  84.52   34
 12  ω     16.00  41.50   0.75    1.23    --   50.00  81.00 177.29   34
 13  ω     16.00  41.50   0.75    1.23    --   50.00  81.00 106.98   34
 14  ω     16.00  41.50   0.75    1.23    --   50.00  81.00-132.72   34
 15  ω     22.00 128.50   0.75    1.23    --   54.00  74.00 -16.46  142
 16  ω     26.00 132.50   0.75    1.23    --   58.00  74.00  18.87  142
 17  ω     30.00 136.50   0.75    1.23    --   62.00  74.00  39.06  142
 18  ω     31.00 136.00   0.75    1.23    --   62.00  72.00-149.28  140
 19  ω     31.00 136.00   0.75    1.23    --   62.00  72.00 101.14  140
 20  ω     34.00 140.50   0.75    1.23    --   66.00  74.00 -68.45  142
 21  ω     34.00 140.50   0.75    1.23    --   66.00  73.00 105.90  142
 22  ω     38.00 144.50   0.75    1.23    --   70.00  73.00-170.34  142
 23  ω     38.00 144.50   0.75    1.23    --   70.00  74.00 115.15  142
 24  ω     38.00 144.50   0.75    1.23    --   70.00  74.00-103.59  142
 25  ω     38.00 144.50   0.75    1.23    --   70.00  73.00-170.34  142
 26  ω     38.00 144.50   0.75    1.23    --   70.00  74.00  42.27  142
 27  ω     42.00 148.50   0.75    1.23    --   74.00  74.00 173.95  142
 28  ω     54.00 153.00   0.75    4.92    --   82.00  56.00 -14.79  132
 29  ω     80.00 177.50   0.75    4.92    --  110.00  67.00  12.84  130
 30  ω     83.00 177.50   0.75    4.92    --  112.00  61.00 150.00  126
 31  ω     36.00 108.00   0.75    4.92    --  112.00-111.00  30.00   96
 32  ω     86.00 177.50   0.75    4.92    --  112.00  45.00 -30.00  122
 33  ω     83.00 177.50   0.75    4.92    --  112.00  61.00 -60.00  126
 34  ω     83.00 177.50   0.75    4.92    --  112.00  61.00 -30.00  126
 35  ω     83.00 177.50   0.75    4.92    --  112.00  61.00  30.00  126
 36  ω     30.00 105.00   0.75    4.92    --  112.00 -95.00-180.00  100
 37  ω     30.00 105.00   0.75    4.92    --  112.00 -95.00 150.00  100
 38  ω     36.00 108.00   0.75    4.92    --  112.00-111.00  90.00   96
 39  ω     36.00 108.00   0.75    4.92    --  112.00-111.00 -30.00   96
 40  ω     83.00 177.50   0.75    4.92    --  112.00  61.00   0.00  126
 41  ω     83.00 177.50   0.75    4.92    --  112.00  61.00-180.00  126
 42  ω     61.00 145.00   0.75    4.92    --  112.00 178.00   0.00  112
 43  ω     83.00 177.50   0.75    4.92    --  112.00  61.00-120.00  126
 44  ω     61.00 145.00   0.75    4.92    --  112.00 178.00 120.00  112
 45  ω     86.00 177.50   0.75    4.92    --  112.00  45.00 -90.00  122
 46  ω     30.00 105.00   0.75    4.92    --  112.00 -95.00-120.00  100
 47  ω     38.00 137.00   0.75    4.92    --  112.00 -38.00  46.32  132
 48  ω     83.00 177.50   0.75    4.92    --  112.00  61.00  90.00  126
 49  ω     36.00 108.00   0.75    4.92    --  112.00-111.00 150.00   96
 50  ω     83.00 177.50   0.75    4.92    --  112.00  61.00 120.00  126
 51  ω     86.00 177.50   0.75    4.92    --  112.00  45.00-180.00  122
 52  ω     33.00 145.50   0.75    4.92    --  112.00 -82.00  -9.19  150
 53  ω     86.00 177.50   0.75    4.92    --  112.00  45.00 150.00  122
 54  ω     83.00 177.50   0.75    4.92    --  112.00  61.00 -90.00  126
 55  ω     86.00 177.50   0.75    4.92    --  112.00  45.00 120.00  122
 56  ω     84.00 177.00   0.75    4.92    --  112.00  30.00 -60.00  124
 57  ω     86.00 177.50   0.75    4.92    --  112.00  45.00  60.00  122
 58  ω    103.00 178.00   0.75    4.92    --  112.00  77.00 150.00  100
 59  ω     39.00 138.00   0.75    4.92    --  112.00 -45.00 120.00  132
 60  ω     86.00 177.50   0.75    4.92    --  112.00  45.00   0.00  122
 61  ω     86.00 177.50   0.75    4.92    --  112.00  45.00-120.00  122
 62  ω     83.00 177.50   0.75    4.92    --  112.00  61.00  60.00  126
 63  ω     86.00 177.50   0.75    4.92    --  112.00  45.00  90.00  122
 64  ω     39.00 138.00   0.75    4.92    --  112.00 -45.00-150.00  132
 65  ω     83.00 177.50   0.75    4.92    --  112.00  61.00-150.00  126
 66  ω     36.00 108.00   0.75    4.92    --  112.00-111.00-120.00   96
 67  ω     40.00 140.50   0.75    4.92    --  112.00 -61.00 -30.00  134
 68  ω      7.00  32.50   0.75    1.23    --   41.35  84.00 -19.86   34
 69  ω     17.00 116.00   0.75    1.23    --   41.35  38.00  30.00  132
 70  ω     16.00  41.50   0.75    1.23    --   50.00  82.00-113.21   34
 71  ω     26.00 132.50   0.75    1.23    --   58.00  74.00 152.50  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0869952000
_diffrn_orient_matrix_UB_12      0.0822578000
_diffrn_orient_matrix_UB_13      -0.0025372000
_diffrn_orient_matrix_UB_21      0.0047493000
_diffrn_orient_matrix_UB_22      -0.1012216000
_diffrn_orient_matrix_UB_23      -0.0345496000
_diffrn_orient_matrix_UB_31      -0.0278817000
_diffrn_orient_matrix_UB_32      0.2392441000
_diffrn_orient_matrix_UB_33      -0.0137473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                8149
_reflns_number_total             8234
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 3843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.64(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8234
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.079
_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)+(0.0540P)²+4.2292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C41) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3. Others
 Sof(H42C)=Sof(H42D)=Sof(H40D)=Sof(H40E)=Sof(H40F)=Sof(C41)=Sof(H41)=1-FVAR(1)
 Sof(H42A)=Sof(H42B)=Sof(C39)=Sof(H39)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17)=Sof(H17)=1-FVAR(2)
 Sof(H18A)=Sof(H18B)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C15)=Sof(H15)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C00G(H00G), C2(H2), C26(H26), C39(H39), C24(H24), C15(H15), C41(H41), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C42(H42A,H42B), C42(H42C,H42D), C18(H18A,H18B), C18(H18C,
 H18D), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C31(H31), C20(H20), C6(H6), C33(H33), C11(H11), C35(H35), C30(H30),
 C23(H23), C44(H44), C46(H46), C45(H45), C22(H22), C21(H21), C32(H32), C47(H47),
  C8(H8), C9(H9), C7(H7), C36(H36)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16(H16D,H16E,H16F), C40(H40A,H40B,H40C), C40(H40D,H40E,
 H40F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O5 O 0.22932(15) 0.4205(5) 0.63029(6) 0.0208(6) Uani 1 1 d . . . . .
O7 O 0.0606(2) 0.2234(5) 0.59417(9) 0.0231(7) Uani 1 1 d . . . . .
O1 O 0.01827(16) 0.9122(5) 0.37009(6) 0.0218(6) Uani 1 1 d . . . . .
O4 O 0.25778(16) 1.0280(5) 0.41870(7) 0.0240(6) Uani 1 1 d . . . . .
O8 O -0.01141(16) 0.5284(5) 0.58183(7) 0.0236(6) Uani 1 1 d . . . . .
O3 O 0.1879(2) 0.7181(5) 0.40643(9) 0.0240(7) Uani 1 1 d . . . . .
N5 N 0.10570(19) 0.8255(6) 0.66193(8) 0.0183(6) Uani 1 1 d . . . . .
O6 O 0.1909(2) 0.3805(6) 0.71062(7) 0.0327(7) Uani 1 1 d . . . . .
N4 N 0.14674(18) 0.6033(6) 0.66821(8) 0.0174(6) Uani 1 1 d . . . . .
O2 O 0.05771(19) 0.8618(6) 0.28995(7) 0.0305(7) Uani 1 1 d . . . . .
N7 N 0.04414(18) 0.4327(6) 0.59609(8) 0.0174(6) Uani 1 1 d . . . . .
N3 N 0.20376(19) 0.9289(6) 0.40418(8) 0.0173(6) Uani 1 1 d . . . . .
N00D N 0.26677(18) 0.9203(6) 0.33479(8) 0.0214(7) Uani 1 1 d . . . . .
N1 N 0.10081(18) 1.0903(6) 0.33196(8) 0.0188(6) Uani 1 1 d . . . . .
N6 N -0.01844(19) 0.4252(6) 0.66563(9) 0.0232(7) Uani 1 1 d . . . . .
C00G C 0.2021(3) 1.2493(6) 0.36241(12) 0.0162(9) Uani 1 1 d . . . . .
H00G H 0.2174 1.3941 0.3748 0.019 Uiso 1 1 calc R U . . .
C27 C 0.1483(3) 0.7299(6) 0.59203(12) 0.0157(9) Uani 1 1 d . . . . .
H27A H 0.1146 0.8042 0.5752 0.019 Uiso 1 1 calc R U . . .
H27B H 0.1778 0.8565 0.6035 0.019 Uiso 1 1 calc R U . . .
C12 C -0.0507(3) 0.7240(8) 0.41395(13) 0.0238(10) Uani 1 1 d . . . . .
H12 H -0.0768 0.6221 0.3990 0.029 Uiso 1 1 calc R U . . .
N2 N 0.14125(19) 1.3113(6) 0.33784(8) 0.0172(6) Uani 1 1 d . . . . .
C31 C 0.2079(3) 0.6846(9) 0.48773(10) 0.0253(9) Uani 1 1 d . . . . .
H31 H 0.1862 0.7942 0.4727 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3496(3) 1.2402(7) 0.35218(13) 0.0203(10) Uani 1 1 d . . . . .
H20 H 0.3545 1.3880 0.3629 0.024 Uiso 1 1 calc R U . . .
C29 C 0.2221(2) 0.5456(7) 0.54285(9) 0.0177(7) Uani 1 1 d . . . . .
C25 C 0.0961(2) 0.5919(6) 0.61619(9) 0.0150(7) Uani 1 1 d . . . . .
C28 C 0.2059(2) 0.5595(7) 0.57658(9) 0.0174(7) Uani 1 1 d . . . . .
C4 C 0.0405(2) 1.0544(7) 0.42349(9) 0.0168(7) Uani 1 1 d . . . . .
C6 C 0.0559(2) 1.2015(8) 0.48038(12) 0.0214(8) Uani 1 1 d . . . . .
H6 H 0.0898 1.3252 0.4731 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2762(2) 1.1297(7) 0.34934(9) 0.0172(7) Uani 1 1 d . . . . .
C13 C 0.0044(2) 0.8971(7) 0.40313(9) 0.0183(7) Uani 1 1 d . . . . .
C37 C 0.2422(2) 0.4049(7) 0.59737(9) 0.0181(7) Uani 1 1 d . . . . .
C5 C 0.0249(2) 1.0416(7) 0.45748(9) 0.0169(7) Uani 1 1 d . . . . .
C2 C 0.0990(2) 0.9422(7) 0.36001(9) 0.0175(7) Uani 1 1 d . . . . .
H2 H 0.1241 0.7855 0.3553 0.021 Uiso 1 1 calc R U . . .
C10 C -0.0274(2) 0.8622(7) 0.46909(10) 0.0200(8) Uani 1 1 d . . . . .
C33 C 0.2902(2) 0.3453(8) 0.49800(10) 0.0249(8) Uani 1 1 d . . . . .
H33 H 0.3235 0.2218 0.4903 0.030 Uiso 1 1 calc R U . . .
C11 C -0.0652(3) 0.7083(8) 0.44638(11) 0.0212(9) Uani 1 1 d . . . . .
H11 H -0.1013 0.5918 0.4541 0.025 Uiso 1 1 calc R U . . .
C34 C 0.2748(2) 0.3642(7) 0.53164(10) 0.0200(8) Uani 1 1 d . . . . .
C35 C 0.3099(3) 0.2107(8) 0.55421(12) 0.0235(9) Uani 1 1 d . . . . .
H35 H 0.3449 0.0904 0.5468 0.028 Uiso 1 1 calc R U . . .
C30 C 0.1896(2) 0.7075(8) 0.51996(11) 0.0191(8) Uani 1 1 d . . . . .
H30 H 0.1553 0.8309 0.5270 0.023 Uiso 1 1 calc R U . . .
C43 C -0.0289(2) 0.6354(7) 0.65090(9) 0.0174(7) Uani 1 1 d . . . . .
C26 C 0.1478(2) 0.4506(7) 0.64036(9) 0.0168(7) Uani 1 1 d . . . . .
H26 H 0.1228 0.2944 0.6455 0.020 Uiso 1 1 calc R U . . .
C42 C 0.0783(2) 0.8990(8) 0.69458(9) 0.0225(8) Uani 1 1 d . . . . .
H42A H 0.0245 0.8370 0.6992 0.027 Uiso 0.822(17) 1 calc R U P A 1
H42B H 0.0777 1.0735 0.6967 0.027 Uiso 0.822(17) 1 calc R U P A 1
H42C H 0.1062 1.0462 0.7009 0.027 Uiso 0.178(17) 1 calc R U P A 2
H42D H 0.0207 0.9338 0.6937 0.027 Uiso 0.178(17) 1 calc R U P A 2
C18 C 0.1701(2) 1.3820(8) 0.30500(10) 0.0226(8) Uani 1 1 d . . . . .
H18A H 0.2246 1.3224 0.3011 0.027 Uiso 0.931(16) 1 calc R U P B 1
H18B H 0.1699 1.5562 0.3025 0.027 Uiso 0.931(16) 1 calc R U P B 1
H18C H 0.1399 1.5215 0.2974 0.027 Uiso 0.069(16) 1 calc R U P B 2
H18D H 0.2269 1.4266 0.3063 0.027 Uiso 0.069(16) 1 calc R U P B 2
C23 C 0.3312(2) 0.8191(8) 0.32190(11) 0.0239(8) Uani 1 1 d . . . . .
H23 H 0.3247 0.6720 0.3111 0.029 Uiso 1 1 calc R U . . .
C38 C 0.1607(3) 0.5605(8) 0.69953(10) 0.0252(8) Uani 1 1 d . . . . .
C14 C 0.0878(2) 1.0428(8) 0.30055(10) 0.0231(8) Uani 1 1 d . . . . .
C44 C -0.1033(3) 0.7424(7) 0.64779(14) 0.0209(10) Uani 1 1 d . . . . .
H44 H -0.1088 0.8899 0.6370 0.025 Uiso 1 1 calc R U . . .
C46 C -0.1591(2) 0.4143(8) 0.67649(10) 0.0241(8) Uani 1 1 d . . . . .
H46 H -0.2031 0.3334 0.6857 0.029 Uiso 1 1 calc R U . . .
C45 C -0.1690(2) 0.6293(8) 0.66076(10) 0.0254(8) Uani 1 1 d . . . . .
H45 H -0.2203 0.6982 0.6589 0.031 Uiso 1 1 calc R U . . .
C1 C 0.1508(2) 1.0865(7) 0.38394(9) 0.0165(7) Uani 1 1 d . . . . .
C22 C 0.4068(2) 0.9153(8) 0.32330(10) 0.0234(8) Uani 1 1 d . . . . .
H22 H 0.4509 0.8363 0.3138 0.028 Uiso 1 1 calc R U . . .
C21 C 0.4161(2) 1.1293(8) 0.33889(10) 0.0241(8) Uani 1 1 d . . . . .
H21 H 0.4670 1.2004 0.3406 0.029 Uiso 1 1 calc R U . . .
C32 C 0.2579(2) 0.5027(8) 0.47644(10) 0.0244(8) Uani 1 1 d . . . . .
H32 H 0.2692 0.4891 0.4540 0.029 Uiso 1 1 calc R U . . .
C47 C -0.0828(3) 0.3213(9) 0.67826(10) 0.0253(8) Uani 1 1 d . . . . .
H47 H -0.0759 0.1746 0.6891 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0106(2) 1.0028(8) 0.52398(10) 0.0242(8) Uani 1 1 d . . . . .
H8 H -0.0216 0.9889 0.5465 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0430(2) 0.8465(7) 0.50253(10) 0.0228(8) Uani 1 1 d . . . . .
H9 H -0.0768 0.7244 0.5103 0.027 Uiso 1 1 calc R U . . .
C16 C 0.1397(4) 1.2184(11) 0.24880(16) 0.0377(13) Uani 1 1 d . . . . .
H16A H 0.1871 1.1182 0.2499 0.057 Uiso 0.931(16) 1 calc R U P B 1
H16B H 0.1531 1.3683 0.2382 0.057 Uiso 0.931(16) 1 calc R U P B 1
H16C H 0.0983 1.1373 0.2364 0.057 Uiso 0.931(16) 1 calc R U P B 1
H16D H 0.0889 1.1401 0.2444 0.057 Uiso 0.069(16) 1 calc R U P B 2
H16E H 0.1811 1.1489 0.2351 0.057 Uiso 0.069(16) 1 calc R U P B 2
H16F H 0.1350 1.3878 0.2441 0.057 Uiso 0.069(16) 1 calc R U P B 2
C7 C 0.0392(2) 1.1849(8) 0.51253(11) 0.0225(8) Uani 1 1 d . . . . .
H7 H 0.0611 1.2963 0.5273 0.027 Uiso 1 1 calc R U . . .
C3 C 0.0983(3) 1.2235(7) 0.40805(12) 0.0178(9) Uani 1 1 d . . . . .
H3A H 0.1319 1.2977 0.4249 0.021 Uiso 1 1 calc R U . . .
H3B H 0.0691 1.3504 0.3966 0.021 Uiso 1 1 calc R U . . .
C39 C 0.1399(3) 0.7889(10) 0.71698(14) 0.0203(15) Uani 0.822(17) 1 d . . P A 1
H39 H 0.1880 0.8929 0.7172 0.024 Uiso 0.822(17) 1 calc R U P A 1
C24 C 0.0444(3) 0.7543(6) 0.63761(12) 0.0155(9) Uani 1 1 d . . . . .
H24 H 0.0282 0.8964 0.6248 0.019 Uiso 1 1 calc R U . . .
C40 C 0.1128(4) 0.7502(9) 0.75196(15) 0.0351(13) Uani 1 1 d . . . . .
H40A H 0.0677 0.6405 0.7523 0.053 Uiso 0.822(17) 1 calc R U P A 1
H40B H 0.0967 0.9019 0.7614 0.053 Uiso 0.822(17) 1 calc R U P A 1
H40C H 0.1567 0.6835 0.7646 0.053 Uiso 0.822(17) 1 calc R U P A 1
H40D H 0.1265 0.5931 0.7603 0.053 Uiso 0.178(17) 1 calc R U P A 2
H40E H 0.0674 0.8134 0.7641 0.053 Uiso 0.178(17) 1 calc R U P A 2
H40F H 0.1584 0.8564 0.7545 0.053 Uiso 0.178(17) 1 calc R U P A 2
C36 C 0.2952(3) 0.2299(7) 0.58650(12) 0.0183(9) Uani 1 1 d . . . . .
H36 H 0.3204 0.1265 0.6015 0.022 Uiso 1 1 calc R U . . .
C15 C 0.1105(3) 1.2658(8) 0.28181(15) 0.0242(14) Uani 0.931(16) 1 d . . P B 1
H15 H 0.0626 1.3698 0.2803 0.029 Uiso 0.931(16) 1 calc R U P B 1
C41 C 0.0917(15) 0.732(4) 0.7172(5) 0.018(6) Uani 0.178(17) 1 d . U P A 2
H41 H 0.0425 0.6326 0.7169 0.021 Uiso 0.178(17) 1 calc R U P A 2
C17 C 0.160(3) 1.187(9) 0.2819(12) 0.012(14) Uani 0.069(16) 1 d . U P B 2
H17 H 0.2092 1.0867 0.2829 0.014 Uiso 0.069(16) 1 calc R U P B 2


_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
O5 C37 1.381(5) . ?
O5 C26 1.444(4) . ?
O7 N7 1.217(4) . ?
O1 C13 1.388(4) . ?
O1 C2 1.431(4) . ?
O4 N3 1.225(4) . ?
O8 N7 1.230(4) . ?
O3 N3 1.224(4) . ?
N5 N4 1.456(5) . ?
N5 C42 1.485(5) . ?
N5 C24 1.496(6) . ?
O6 C38 1.226(5) . ?
N4 C26 1.438(5) . ?
N4 C38 1.337(5) . ?
O2 C14 1.222(5) . ?
N7 C25 1.505(5) . ?
N3 C1 1.513(5) . ?
N00D C19 1.337(5) . ?
N00D C23 1.337(5) . ?
N1 N2 1.443(5) . ?
N1 C2 1.430(5) . ?
N1 C14 1.343(5) . ?
N6 C43 1.346(5) . ?
N6 C47 1.338(5) . ?
C00G H00G 1.0000 . ?
C00G N2 1.484(6) . ?
C00G C19 1.518(5) . ?
C00G C1 1.544(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C25 1.542(5) . ?
C27 C28 1.508(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.420(6) . ?
C12 C11 1.365(7) . ?
N2 C18 1.496(5) . ?
C31 H31 0.9500 . ?
C31 C30 1.373(6) . ?
C31 C32 1.408(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.389(6) . ?
C20 C21 1.394(6) . ?
C29 C28 1.422(5) . ?
C29 C34 1.433(5) . ?
C29 C30 1.425(6) . ?
C25 C26 1.546(5) . ?
C25 C24 1.544(6) . ?
C28 C37 1.369(5) . ?
C4 C13 1.367(5) . ?
C4 C5 1.431(5) . ?
C4 C3 1.506(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.409(6) . ?
C6 C7 1.361(7) . ?
C37 C36 1.405(6) . ?
C5 C10 1.426(5) . ?
C2 H2 1.0000 . ?
C2 C1 1.549(5) . ?
C10 C11 1.428(6) . ?
C10 C9 1.409(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.418(6) . ?
C33 C32 1.372(6) . ?
C11 H11 0.9500 . ?
C34 C35 1.404(6) . ?
C35 H35 0.9500 . ?
C35 C36 1.361(7) . ?
C30 H30 0.9500 . ?
C43 C44 1.397(6) . ?
C43 C24 1.508(6) . ?
C26 H26 1.0000 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 H42C 0.9900 . ?
C42 H42D 0.9900 . ?
C42 C39 1.522(7) . ?
C42 C41 1.35(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C18 C15 1.534(7) . ?
C18 C17 1.47(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.386(6) . ?
C38 C39 1.519(7) . ?
C38 C41 1.68(2) . ?
C14 C15 1.528(6) . ?
C14 C17 1.66(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.384(6) . ?
C46 H46 0.9500 . ?
C46 C45 1.388(6) . ?
C46 C47 1.389(6) . ?
C45 H45 0.9500 . ?
C1 C3 1.540(6) . ?
C22 H22 0.9500 . ?
C22 C21 1.379(6) . ?
C21 H21 0.9500 . ?
C32 H32 0.9500 . ?
C47 H47 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.364(6) . ?
C8 C7 1.409(6) . ?
C9 H9 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C16 C15 1.474(9) . ?
C16 C17 1.42(5) . ?
C7 H7 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C39 H39 1.0000 . ?
C39 C40 1.531(8) . ?
C24 H24 1.0000 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C40 H40D 0.9800 . ?
C40 H40E 0.9800 . ?
C40 H40F 0.9800 . ?
C40 C41 1.48(2) . ?
C36 H36 0.9500 . ?
C15 H15 1.0000 . ?
C41 H41 1.0000 . ?
C17 H17 1.0000 . ?

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
C37 O5 C26 116.2(3) . . ?
C13 O1 C2 117.0(3) . . ?
N4 N5 C42 103.1(3) . . ?
N4 N5 C24 102.4(3) . . ?
C42 N5 C24 118.1(3) . . ?
C26 N4 N5 112.3(3) . . ?
C38 N4 N5 114.3(3) . . ?
C38 N4 C26 131.6(3) . . ?
O7 N7 O8 124.7(4) . . ?
O7 N7 C25 119.0(3) . . ?
O8 N7 C25 116.3(3) . . ?
O4 N3 C1 116.1(3) . . ?
O3 N3 O4 124.7(4) . . ?
O3 N3 C1 119.1(3) . . ?
C23 N00D C19 117.5(3) . . ?
C2 N1 N2 112.3(3) . . ?
C14 N1 N2 114.4(3) . . ?
C14 N1 C2 131.5(3) . . ?
C47 N6 C43 117.2(4) . . ?
N2 C00G H00G 109.6 . . ?
N2 C00G C19 115.4(4) . . ?
N2 C00G C1 98.6(3) . . ?
C19 C00G H00G 109.6 . . ?
C19 C00G C1 113.5(3) . . ?
C1 C00G H00G 109.6 . . ?
H27A C27 H27B 108.4 . . ?
C25 C27 H27A 110.0 . . ?
C25 C27 H27B 110.0 . . ?
C28 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
C28 C27 C25 108.5(3) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(4) . . ?
N1 N2 C00G 103.6(3) . . ?
N1 N2 C18 103.4(3) . . ?
C00G N2 C18 117.4(3) . . ?
C30 C31 H31 119.2 . . ?
C30 C31 C32 121.6(4) . . ?
C32 C31 H31 119.2 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.6(4) . . ?
C21 C20 H20 120.7 . . ?
C28 C29 C34 118.3(3) . . ?
C28 C29 C30 122.8(4) . . ?
C30 C29 C34 118.9(4) . . ?
N7 C25 C27 106.1(3) . . ?
N7 C25 C26 112.0(3) . . ?
N7 C25 C24 110.1(3) . . ?
C27 C25 C26 111.0(3) . . ?
C27 C25 C24 113.1(3) . . ?
C24 C25 C26 104.7(3) . . ?
C29 C28 C27 125.0(4) . . ?
C37 C28 C27 115.4(3) . . ?
C37 C28 C29 119.6(3) . . ?
C13 C4 C5 119.3(3) . . ?
C13 C4 C3 116.1(4) . . ?
C5 C4 C3 124.5(4) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C7 C6 C5 122.3(4) . . ?
N00D C19 C00G 117.1(3) . . ?
N00D C19 C20 122.8(4) . . ?
C20 C19 C00G 120.1(4) . . ?
O1 C13 C12 117.5(4) . . ?
C4 C13 O1 119.4(3) . . ?
C4 C13 C12 123.0(4) . . ?
O5 C37 C36 117.4(3) . . ?
C28 C37 O5 120.5(3) . . ?
C28 C37 C36 122.1(4) . . ?
C6 C5 C4 123.9(4) . . ?
C6 C5 C10 117.3(4) . . ?
C10 C5 C4 118.7(3) . . ?
O1 C2 H2 110.6 . . ?
O1 C2 C1 114.2(3) . . ?
N1 C2 O1 109.0(3) . . ?
N1 C2 H2 110.6 . . ?
N1 C2 C1 101.4(3) . . ?
C1 C2 H2 110.6 . . ?
C5 C10 C11 119.1(4) . . ?
C9 C10 C5 119.3(4) . . ?
C9 C10 C11 121.5(4) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 121.0(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C33 C34 C29 119.0(4) . . ?
C35 C34 C29 119.2(4) . . ?
C35 C34 C33 121.8(4) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 C34 121.6(4) . . ?
C36 C35 H35 119.2 . . ?
C31 C30 C29 119.8(4) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
N6 C43 C44 122.7(4) . . ?
N6 C43 C24 116.8(3) . . ?
C44 C43 C24 120.5(4) . . ?
O5 C26 C25 114.1(3) . . ?
O5 C26 H26 110.8 . . ?
N4 C26 O5 108.2(3) . . ?
N4 C26 C25 101.6(3) . . ?
N4 C26 H26 110.8 . . ?
C25 C26 H26 110.8 . . ?
N5 C42 H42A 111.1 . . ?
N5 C42 H42B 111.1 . . ?
N5 C42 H42C 109.1 . . ?
N5 C42 H42D 109.1 . . ?
N5 C42 C39 103.1(3) . . ?
H42A C42 H42B 109.1 . . ?
H42C C42 H42D 107.9 . . ?
C39 C42 H42A 111.1 . . ?
C39 C42 H42B 111.1 . . ?
C41 C42 N5 112.4(10) . . ?
C41 C42 H42C 109.1 . . ?
C41 C42 H42D 109.1 . . ?
N2 C18 H18A 111.0 . . ?
N2 C18 H18B 111.0 . . ?
N2 C18 H18C 109.5 . . ?
N2 C18 H18D 109.5 . . ?
N2 C18 C15 103.9(4) . . ?
H18A C18 H18B 109.0 . . ?
H18C C18 H18D 108.1 . . ?
C15 C18 H18A 111.0 . . ?
C15 C18 H18B 111.0 . . ?
C17 C18 N2 111(2) . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
N00D C23 H23 117.9 . . ?
N00D C23 C22 124.1(4) . . ?
C22 C23 H23 117.9 . . ?
O6 C38 N4 125.8(4) . . ?
O6 C38 C39 128.6(4) . . ?
O6 C38 C41 127.1(8) . . ?
N4 C38 C39 105.4(4) . . ?
N4 C38 C41 101.2(8) . . ?
O2 C14 N1 125.5(4) . . ?
O2 C14 C15 127.7(4) . . ?
O2 C14 C17 123.4(18) . . ?
N1 C14 C15 106.5(4) . . ?
N1 C14 C17 103.3(18) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 C43 118.7(4) . . ?
C45 C44 H44 120.6 . . ?
C45 C46 H46 121.1 . . ?
C45 C46 C47 117.8(4) . . ?
C47 C46 H46 121.1 . . ?
C44 C45 C46 119.4(4) . . ?
C44 C45 H45 120.3 . . ?
C46 C45 H45 120.3 . . ?
N3 C1 C00G 109.9(3) . . ?
N3 C1 C2 112.0(3) . . ?
N3 C1 C3 106.0(3) . . ?
C00G C1 C2 105.1(3) . . ?
C3 C1 C00G 113.2(3) . . ?
C3 C1 C2 110.8(3) . . ?
C23 C22 H22 121.1 . . ?
C21 C22 C23 117.8(4) . . ?
C21 C22 H22 121.1 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.7(4) . . ?
C33 C32 H32 120.2 . . ?
N6 C47 C46 124.2(4) . . ?
N6 C47 H47 117.9 . . ?
C46 C47 H47 117.9 . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C10 C9 H9 119.3 . . ?
C8 C9 C10 121.5(4) . . ?
C8 C9 H9 119.3 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C17 C16 H16D 109.5 . . ?
C17 C16 H16E 109.5 . . ?
C17 C16 H16F 109.5 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C4 C3 C1 109.0(3) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C1 C3 H3A 109.9 . . ?
C1 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C42 C39 H39 108.4 . . ?
C42 C39 C40 115.4(5) . . ?
C38 C39 C42 102.5(4) . . ?
C38 C39 H39 108.4 . . ?
C38 C39 C40 113.3(5) . . ?
C40 C39 H39 108.4 . . ?
N5 C24 C25 99.0(3) . . ?
N5 C24 C43 116.1(4) . . ?
N5 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C43 C24 C25 113.9(3) . . ?
C43 C24 H24 109.1 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
H40D C40 H40E 109.5 . . ?
H40D C40 H40F 109.5 . . ?
H40E C40 H40F 109.5 . . ?
C41 C40 H40D 109.5 . . ?
C41 C40 H40E 109.5 . . ?
C41 C40 H40F 109.5 . . ?
C37 C36 H36 120.5 . . ?
C35 C36 C37 119.0(4) . . ?
C35 C36 H36 120.5 . . ?
C18 C15 H15 108.4 . . ?
C14 C15 C18 101.5(4) . . ?
C14 C15 H15 108.4 . . ?
C16 C15 C18 116.0(5) . . ?
C16 C15 C14 113.7(4) . . ?
C16 C15 H15 108.4 . . ?
C42 C41 C38 102.7(14) . . ?
C42 C41 C40 131.4(16) . . ?
C42 C41 H41 104.3 . . ?
C38 C41 H41 104.3 . . ?
C40 C41 C38 107.2(14) . . ?
C40 C41 H41 104.3 . . ?
C18 C17 C14 99(3) . . ?
C18 C17 H17 108.0 . . ?
C14 C17 H17 108.0 . . ?
C16 C17 C18 124(4) . . ?
C16 C17 C14 109(3) . . ?
C16 C17 H17 108.0 . . ?

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
O5 C37 C36 C35 -179.4(4) . . . . ?
O7 N7 C25 C27 102.8(4) . . . . ?
O7 N7 C25 C26 -18.5(5) . . . . ?
O7 N7 C25 C24 -134.6(4) . . . . ?
O1 C2 C1 N3 102.0(4) . . . . ?
O1 C2 C1 C00G -138.8(3) . . . . ?
O1 C2 C1 C3 -16.2(4) . . . . ?
O4 N3 C1 C00G 49.0(4) . . . . ?
O4 N3 C1 C2 165.4(3) . . . . ?
O4 N3 C1 C3 -73.7(4) . . . . ?
O8 N7 C25 C27 -75.1(4) . . . . ?
O8 N7 C25 C26 163.6(3) . . . . ?
O8 N7 C25 C24 47.6(4) . . . . ?
O3 N3 C1 C00G -134.9(4) . . . . ?
O3 N3 C1 C2 -18.6(5) . . . . ?
O3 N3 C1 C3 102.4(4) . . . . ?
N5 N4 C26 O5 115.8(3) . . . . ?
N5 N4 C26 C25 -4.7(4) . . . . ?
N5 N4 C38 O6 176.3(4) . . . . ?
N5 N4 C38 C39 -9.6(5) . . . . ?
N5 N4 C38 C41 22.2(9) . . . . ?
N5 C42 C39 C38 -33.9(5) . . . . ?
N5 C42 C39 C40 -157.5(4) . . . . ?
N5 C42 C41 C38 18.7(16) . . . . ?
N5 C42 C41 C40 145.8(19) . . . . ?
O6 C38 C39 C42 -159.2(5) . . . . ?
O6 C38 C39 C40 -34.2(8) . . . . ?
O6 C38 C41 C42 -178.5(8) . . . . ?
O6 C38 C41 C40 40.4(19) . . . . ?
N4 N5 C42 C39 28.4(4) . . . . ?
N4 N5 C42 C41 -6.9(13) . . . . ?
N4 N5 C24 C25 -42.5(3) . . . . ?
N4 N5 C24 C43 79.8(4) . . . . ?
N4 C38 C39 C42 27.0(5) . . . . ?
N4 C38 C39 C40 152.0(4) . . . . ?
N4 C38 C41 C42 -24.8(15) . . . . ?
N4 C38 C41 C40 -165.9(11) . . . . ?
O2 C14 C15 C18 -160.4(4) . . . . ?
O2 C14 C15 C16 -35.2(7) . . . . ?
O2 C14 C17 C18 179.2(12) . . . . ?
O2 C14 C17 C16 49(4) . . . . ?
N7 C25 C26 O5 101.6(3) . . . . ?
N7 C25 C26 N4 -142.2(3) . . . . ?
N7 C25 C24 N5 161.4(3) . . . . ?
N7 C25 C24 C43 37.6(5) . . . . ?
N3 C1 C3 C4 -69.6(4) . . . . ?
N00D C23 C22 C21 -0.3(6) . . . . ?
N1 N2 C18 C15 27.3(4) . . . . ?
N1 N2 C18 C17 -11(2) . . . . ?
N1 C2 C1 N3 -141.0(3) . . . . ?
N1 C2 C1 C00G -21.8(4) . . . . ?
N1 C2 C1 C3 100.8(3) . . . . ?
N1 C14 C15 C18 24.9(5) . . . . ?
N1 C14 C15 C16 150.2(4) . . . . ?
N1 C14 C17 C18 -30(3) . . . . ?
N1 C14 C17 C16 -161(3) . . . . ?
N6 C43 C44 C45 0.9(7) . . . . ?
N6 C43 C24 N5 -63.8(4) . . . . ?
N6 C43 C24 C25 50.3(5) . . . . ?
C00G N2 C18 C15 140.7(4) . . . . ?
C00G N2 C18 C17 103(2) . . . . ?
C00G C1 C3 C4 169.9(3) . . . . ?
C27 C25 C26 O5 -16.8(4) . . . . ?
C27 C25 C26 N4 99.4(3) . . . . ?
C27 C25 C24 N5 -80.1(4) . . . . ?
C27 C25 C24 C43 156.0(4) . . . . ?
C27 C28 C37 O5 -4.1(5) . . . . ?
C27 C28 C37 C36 177.7(4) . . . . ?
N2 N1 C2 O1 115.6(3) . . . . ?
N2 N1 C2 C1 -5.2(4) . . . . ?
N2 N1 C14 O2 176.7(4) . . . . ?
N2 N1 C14 C15 -8.5(5) . . . . ?
N2 N1 C14 C17 27(2) . . . . ?
N2 C00G C19 N00D -62.1(5) . . . . ?
N2 C00G C19 C20 116.6(4) . . . . ?
N2 C00G C1 N3 159.9(3) . . . . ?
N2 C00G C1 C2 39.3(3) . . . . ?
N2 C00G C1 C3 -81.7(4) . . . . ?
N2 C18 C15 C14 -31.7(4) . . . . ?
N2 C18 C15 C16 -155.5(4) . . . . ?
N2 C18 C17 C14 24(3) . . . . ?
N2 C18 C17 C16 144(3) . . . . ?
C29 C28 C37 O5 177.9(3) . . . . ?
C29 C28 C37 C36 -0.4(6) . . . . ?
C29 C34 C35 C36 0.0(6) . . . . ?
C25 C27 C28 C29 133.4(4) . . . . ?
C25 C27 C28 C37 -44.6(5) . . . . ?
C28 C27 C25 N7 -68.8(4) . . . . ?
C28 C27 C25 C26 53.1(4) . . . . ?
C28 C27 C25 C24 170.4(3) . . . . ?
C28 C29 C34 C33 178.8(4) . . . . ?
C28 C29 C34 C35 -1.5(5) . . . . ?
C28 C29 C30 C31 179.7(4) . . . . ?
C28 C37 C36 C35 -1.1(6) . . . . ?
C4 C5 C10 C11 -2.7(6) . . . . ?
C4 C5 C10 C9 179.6(3) . . . . ?
C6 C5 C10 C11 175.1(4) . . . . ?
C6 C5 C10 C9 -2.6(6) . . . . ?
C19 N00D C23 C22 1.4(6) . . . . ?
C19 C00G N2 N1 79.6(4) . . . . ?
C19 C00G N2 C18 -33.6(5) . . . . ?
C19 C00G C1 N3 37.3(5) . . . . ?
C19 C00G C1 C2 -83.3(4) . . . . ?
C19 C00G C1 C3 155.6(4) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C13 O1 C2 N1 -144.9(3) . . . . ?
C13 O1 C2 C1 -32.3(5) . . . . ?
C13 C12 C11 C10 0.9(7) . . . . ?
C13 C4 C5 C6 -176.9(4) . . . . ?
C13 C4 C5 C10 0.8(5) . . . . ?
C13 C4 C3 C1 -43.8(5) . . . . ?
C37 O5 C26 N4 -144.1(3) . . . . ?
C37 O5 C26 C25 -31.9(4) . . . . ?
C5 C4 C13 O1 178.8(3) . . . . ?
C5 C4 C13 C12 2.2(6) . . . . ?
C5 C4 C3 C1 132.9(4) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C5 C10 C11 C12 1.9(7) . . . . ?
C5 C10 C9 C8 1.6(6) . . . . ?
C2 O1 C13 C12 -137.6(4) . . . . ?
C2 O1 C13 C4 45.6(5) . . . . ?
C2 N1 N2 C00G 31.3(4) . . . . ?
C2 N1 N2 C18 154.3(3) . . . . ?
C2 N1 C14 O2 13.4(7) . . . . ?
C2 N1 C14 C15 -171.8(4) . . . . ?
C2 N1 C14 C17 -136(2) . . . . ?
C2 C1 C3 C4 52.1(4) . . . . ?
C33 C34 C35 C36 179.7(4) . . . . ?
C11 C12 C13 O1 -179.7(4) . . . . ?
C11 C12 C13 C4 -3.1(7) . . . . ?
C11 C10 C9 C8 -176.0(4) . . . . ?
C34 C29 C28 C27 -176.2(3) . . . . ?
C34 C29 C28 C37 1.6(5) . . . . ?
C34 C29 C30 C31 1.2(6) . . . . ?
C34 C33 C32 C31 -0.7(6) . . . . ?
C34 C35 C36 C37 1.3(6) . . . . ?
C30 C31 C32 C33 -0.8(7) . . . . ?
C30 C29 C28 C27 5.3(6) . . . . ?
C30 C29 C28 C37 -176.9(4) . . . . ?
C30 C29 C34 C33 -2.6(5) . . . . ?
C30 C29 C34 C35 177.1(4) . . . . ?
C43 N6 C47 C46 1.4(6) . . . . ?
C43 C44 C45 C46 0.2(7) . . . . ?
C26 O5 C37 C28 45.5(5) . . . . ?
C26 O5 C37 C36 -136.2(4) . . . . ?
C26 N4 C38 O6 12.9(7) . . . . ?
C26 N4 C38 C39 -173.1(4) . . . . ?
C26 N4 C38 C41 -141.3(9) . . . . ?
C26 C25 C24 N5 40.9(3) . . . . ?
C26 C25 C24 C43 -83.0(4) . . . . ?
C42 N5 N4 C26 154.4(3) . . . . ?
C42 N5 N4 C38 -12.3(4) . . . . ?
C42 N5 C24 C25 -154.9(3) . . . . ?
C42 N5 C24 C43 -32.6(5) . . . . ?
C23 N00D C19 C00G 176.9(4) . . . . ?
C23 N00D C19 C20 -1.7(6) . . . . ?
C23 C22 C21 C20 -0.6(6) . . . . ?
C38 N4 C26 O5 -80.5(5) . . . . ?
C38 N4 C26 C25 159.1(4) . . . . ?
C14 N1 N2 C00G -135.3(3) . . . . ?
C14 N1 N2 C18 -12.3(4) . . . . ?
C14 N1 C2 O1 -80.8(5) . . . . ?
C14 N1 C2 C1 158.4(4) . . . . ?
C44 C43 C24 N5 116.2(4) . . . . ?
C44 C43 C24 C25 -129.8(4) . . . . ?
C45 C46 C47 N6 -0.4(7) . . . . ?
C1 C00G N2 N1 -41.7(3) . . . . ?
C1 C00G N2 C18 -154.9(3) . . . . ?
C1 C00G C19 N00D 50.7(5) . . . . ?
C1 C00G C19 C20 -130.6(4) . . . . ?
C21 C20 C19 N00D 0.9(7) . . . . ?
C21 C20 C19 C00G -177.7(4) . . . . ?
C32 C31 C30 C29 0.5(7) . . . . ?
C32 C33 C34 C29 2.4(6) . . . . ?
C32 C33 C34 C35 -177.4(4) . . . . ?
C47 N6 C43 C44 -1.6(6) . . . . ?
C47 N6 C43 C24 178.3(4) . . . . ?
C47 C46 C45 C44 -0.4(6) . . . . ?
C9 C10 C11 C12 179.5(4) . . . . ?
C9 C8 C7 C6 -1.3(6) . . . . ?
C7 C6 C5 C4 179.4(4) . . . . ?
C7 C6 C5 C10 1.7(6) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C3 C4 C13 O1 -4.4(5) . . . . ?
C3 C4 C13 C12 179.0(4) . . . . ?
C3 C4 C5 C6 6.5(6) . . . . ?
C3 C4 C5 C10 -175.8(4) . . . . ?
C24 N5 N4 C26 31.2(4) . . . . ?
C24 N5 N4 C38 -135.5(4) . . . . ?
C24 N5 C42 C39 140.4(4) . . . . ?
C24 N5 C42 C41 105.1(12) . . . . ?
C24 C25 C26 O5 -139.1(3) . . . . ?
C24 C25 C26 N4 -23.0(4) . . . . ?
C24 C43 C44 C45 -179.0(4) . . . . ?

_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 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.739

