# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_hxy_3
_audit_block_doi                 10.5517/ccdc.csd.cc2kyd1z
_database_code_depnum_ccdc_archive 'CCDC 2381731'
loop_
_audit_author_name
_audit_author_address
'Ling Huang'
;Institute of Medicinal Biotechnology
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-06-13
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H24 N2 O'
_chemical_formula_sum            'C26 H24 N2 O'
_chemical_formula_weight         380.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H24 N2 O'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.50530(10)
_cell_length_b                   11.21780(10)
_cell_length_c                   18.29070(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1950.31(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26462
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      77.4230
_cell_measurement_theta_min      3.9290
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30036
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.586
_diffrn_reflns_theta_min         4.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  62.00   0.50    0.05    --  106.25 -57.00 -30.00   50
  2  ω     34.00  59.00   0.50    0.05    --  106.25 -57.00  30.00   50
  3  ω     38.00  63.00   0.50    0.05    --  106.25 -57.00  60.00   50
  4  ω     34.00 102.00   0.50    0.05    --  106.25 -77.00  60.00  136
  5  ω    102.00 173.00   0.50    0.05    --  106.25  19.00  90.00  142
  6  ω     -3.00  22.00   0.50    0.05    --   45.56 -19.00 -30.00   50
  7  ω    -29.00  15.00   0.50    0.05    --   45.56 -19.00-120.00   88
  8  ω    -12.00  23.00   0.50    0.05    --   45.56 -19.00-180.00   70
  9  ω    -49.00  20.00   0.50    0.05    --  -45.56  96.00   5.00  138
 10  ω    -21.00  30.00   0.50    0.05    --  -45.56  19.00 150.00  102
 11  ω    -96.00 -59.00   0.50    0.05    --  -97.00  74.00 120.00   74
 12  ω    -69.00 -44.00   0.50    0.05    --  -97.00  57.00 -30.00   50
 13  ω    -66.00 -31.00   0.50    0.05    --  -97.00  56.00 -92.00   70
 14  ω   -114.00 -83.00   0.50    0.05    --  -97.00 -57.00 -60.00   62
 15  ω   -140.00 -84.00   0.50    0.05    --  -97.00 -56.00 125.00  112
 16  ω   -169.00-133.00   0.50    0.05    --  -97.00 -57.00 -60.00   72
 17  ω   -168.00 -82.00   0.50    0.05    --  -97.00 -57.00 -90.00  172
 18  ω   -164.00 -97.00   0.50    0.05    --  -97.00 -96.00-103.00  134
 19  ω   -164.00-139.00   0.50    0.05    --  -97.00-125.00-120.00   50
 20  ω   -117.00 -91.00   0.50    0.05    --  -97.00-125.00-120.00   52
 21  ω    -52.00 -27.00   0.50    0.05    --  -45.81  96.00   5.00   50
 22  ω    -90.00 -65.00   0.50    0.05    --  -97.00  96.00   5.00   50
 23  ω   -168.00-142.00   0.50    0.05    --  -97.00 -96.00-103.00   52
 24  ω   -152.00-127.00   0.50    0.05    --  -97.00 -96.00-103.00   50
 25  ω   -152.00-127.00   0.50    0.05    --  -97.00 -96.00-103.00   50
 26  ω   -111.00 -79.00   0.50    0.05    --  -45.81 -74.00  -7.00   64
 27  ω    -74.00 -43.00   0.50    0.05    --  -45.81 -74.00  -7.00   62
 28  ω   -145.00 -94.00   0.50    0.05    --  -97.00 -99.00-180.00  102
 29  ω    104.00 130.00   0.50    0.05    --  106.25  19.00 -60.00   52
 30  ω     77.00 102.00   0.50    0.05    --  106.25 -77.00 -30.00   50
 31  ω     81.00 106.00   0.50    0.05    --  106.25 -99.00-150.00   50
 32  ω    150.00 175.00   0.50    0.05    --  106.25  19.00 -60.00   50
 33  ω     35.00  60.00   0.50    0.05    --  106.25 -77.00 -30.00   50
 34  ω     34.00  59.00   0.50    0.05    --  106.25 -57.00 -60.00   50
 35  ω     39.00  64.00   0.50    0.05    --  106.25 -74.00  -7.00   50
 36  ω     23.00 118.00   0.50    0.05    --   45.81  77.00  30.00  190
 37  ω     31.00 117.00   0.50    0.05    --   45.81  57.00-180.00  172
 38  ω     42.00  83.00   0.50    0.05    --   45.81  74.00 120.00   82
 39  ω    -65.00 -39.00   0.50    0.05    --  -45.81 125.00 -90.00   52
 40  ω     36.00  62.00   0.50    0.05    --   45.81  38.00-120.00   52
 41  ω      4.00  40.00   0.50    0.05    --   45.81 -38.00   0.00   72
 42  ω     69.00  95.00   0.50    0.05    --   45.81  38.00-120.00   52
 43  ω   -153.00-127.00   0.50    0.05    --  -97.00 -38.00  60.00   52
 44  ω   -157.00-131.00   0.50    0.05    --  -97.00 -57.00-120.00   52
 45  ω   -172.00 -93.00   0.50    0.05    --  -97.00 -19.00 -60.00  158
 46  ω   -123.00 -84.00   0.50    0.05    --  -97.00 -57.00-120.00   78
 47  ω   -114.00 -85.00   0.50    0.05    --  -97.00 -38.00  60.00   58
 48  ω     37.00  63.00   0.50    0.05    --  106.25 -57.00 -90.00   52
 49  ω    133.00 166.00   0.50    0.05    --  106.25  57.00  60.00   66
 50  ω    130.00 162.00   0.50    0.05    --  106.25  77.00  30.00   64
 51  ω     47.00  78.00   0.50    0.05    --  106.25 -99.00 -30.00   62
 52  ω     34.00  60.00   0.50    0.05    --  106.25 -57.00-180.00   52
 53  ω     98.00 123.00   0.50    0.05    --  106.25  57.00  60.00   50
 54  ω    107.00 157.00   0.50    0.05    --  106.25  19.00-180.00  100
 55  ω     85.00 110.00   0.50    0.05    --  106.25  77.00  30.00   50
 56  ω     58.00  84.00   0.50    0.05    --  106.25 -77.00  30.00   52
 57  ω     34.00  59.00   0.50    0.05    --  106.25 -57.00 120.00   50
 58  ω     34.00  59.00   0.50    0.05    --  106.25 -57.00-150.00   50
 59  ω    121.00 165.00   0.50    0.05    --  106.25  19.00 -90.00   88
 60  ω     76.00 111.00   0.50    0.05    --  106.25-125.00 -30.00   70
 61  ω     75.00 100.00   0.50    0.05    --  106.25 -77.00-150.00   50
 62  ω     41.00  67.00   0.50    0.05    --  106.25-125.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0990775000
_diffrn_orient_matrix_UB_12      -0.0624148000
_diffrn_orient_matrix_UB_13      0.0545353000
_diffrn_orient_matrix_UB_21      0.1144846000
_diffrn_orient_matrix_UB_22      -0.0936999000
_diffrn_orient_matrix_UB_23      0.0157876000
_diffrn_orient_matrix_UB_31      0.0579434000
_diffrn_orient_matrix_UB_32      0.0785819000
_diffrn_orient_matrix_UB_33      0.0622172000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                3999
_reflns_number_total             4013
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.063
_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)+(0.0364P)²+0.3350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0652
_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 Secondary CH2 refined with riding coordinates:
 C00E(H00D,H00E), C00N(H00G,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00P(H00Q), C00Q(H00R),
 C00S(H00V), C00T(H00W)
2.c Idealised Me refined as rotating group:
 C00O(H00N,H00O,H00P), C00R(H00S,H00T,H00U)
;
_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
O001 O 0.91296(12) 0.66671(10) 0.67850(6) 0.0281(2) Uani 1 1 d . . . . .
N002 N 0.77571(12) 0.56470(10) 0.59864(6) 0.0182(2) Uani 1 1 d . . . . .
N003 N 0.76070(12) 0.16667(11) 0.64982(6) 0.0192(2) Uani 1 1 d . . . . .
C004 C 0.69760(14) 0.14928(11) 0.58327(7) 0.0157(3) Uani 1 1 d . . . . .
C005 C 0.51773(13) 0.30967(12) 0.61741(7) 0.0157(3) Uani 1 1 d . . . . .
C006 C 0.57946(14) 0.22207(11) 0.56442(7) 0.0160(3) Uani 1 1 d . . . . .
C007 C 0.74995(14) 0.06531(11) 0.53161(7) 0.0168(3) Uani 1 1 d . . . . .
C008 C 0.57613(14) 0.42423(12) 0.62309(7) 0.0172(3) Uani 1 1 d . . . . .
C009 C 0.69104(14) 0.05995(12) 0.46046(7) 0.0194(3) Uani 1 1 d . . . . .
H009 H 0.7264 0.0048 0.4256 0.023 Uiso 1 1 calc R U . . .
C00A C 0.52607(14) 0.21363(12) 0.49475(7) 0.0193(3) Uani 1 1 d . . . . .
H00A H 0.4485 0.2624 0.4814 0.023 Uiso 1 1 calc R U . . .
C00B C 0.51641(15) 0.50748(12) 0.67029(7) 0.0193(3) Uani 1 1 d . . . . .
H00B H 0.5557 0.5851 0.6739 0.023 Uiso 1 1 calc R U . . .
C00C C 0.69476(16) 0.72602(13) 0.42702(8) 0.0216(3) Uani 1 1 d . . . . .
H00C H 0.6057 0.7566 0.4413 0.026 Uiso 1 1 calc R U . . .
C00D C 0.85671(14) 0.57269(13) 0.65990(7) 0.0195(3) Uani 1 1 d . . . . .
C00E C 0.70338(14) 0.45548(12) 0.57665(7) 0.0182(3) Uani 1 1 d . . . . .
H00D H 0.7711 0.3885 0.5788 0.022 Uiso 1 1 calc R U . . .
H00E H 0.6728 0.4639 0.5252 0.022 Uiso 1 1 calc R U . . .
C00F C 0.91111(15) 0.62686(12) 0.45704(7) 0.0205(3) Uani 1 1 d . . . . .
H00F H 0.9708 0.5893 0.4917 0.025 Uiso 1 1 calc R U . . .
C00G C 0.78220(14) 0.67350(12) 0.47924(7) 0.0188(3) Uani 1 1 d . . . . .
C00H C 0.39953(15) 0.47755(13) 0.71217(8) 0.0210(3) Uani 1 1 d . . . . .
H00H H 0.3594 0.5345 0.7445 0.025 Uiso 1 1 calc R U . . .
C00I C 0.34160(15) 0.36425(13) 0.70662(7) 0.0205(3) Uani 1 1 d . . . . .
H00I H 0.2622 0.3440 0.7356 0.025 Uiso 1 1 calc R U . . .
C00J C 0.86602(15) -0.00642(12) 0.55252(8) 0.0214(3) Uani 1 1 d . . . . .
H00J H 0.9013 -0.0658 0.5203 0.026 Uiso 1 1 calc R U . . .
C00K C 0.58306(15) 0.13469(13) 0.44259(7) 0.0212(3) Uani 1 1 d . . . . .
H00K H 0.5458 0.1335 0.3944 0.025 Uiso 1 1 calc R U . . .
C00L C 0.39827(14) 0.27960(12) 0.65902(7) 0.0181(3) Uani 1 1 d . . . . .
C00M C 0.95289(15) 0.63505(12) 0.38427(8) 0.0217(3) Uani 1 1 d . . . . .
H00M H 1.0412 0.6032 0.3697 0.026 Uiso 1 1 calc R U . . .
C00N C 0.73756(16) 0.67326(12) 0.55887(8) 0.0218(3) Uani 1 1 d . . . . .
H00G H 0.7812 0.7425 0.5836 0.026 Uiso 1 1 calc R U . . .
H00L H 0.6342 0.6836 0.5613 0.026 Uiso 1 1 calc R U . . .
C00O C 0.33065(15) 0.15896(13) 0.65258(8) 0.0243(3) Uani 1 1 d . . . . .
H00N H 0.3052 0.1441 0.6015 0.036 Uiso 1 1 calc R U . . .
H00O H 0.2458 0.1564 0.6830 0.036 Uiso 1 1 calc R U . . .
H00P H 0.3969 0.0976 0.6691 0.036 Uiso 1 1 calc R U . . .
C00P C 0.86682(16) 0.68923(12) 0.33295(8) 0.0220(3) Uani 1 1 d . . . . .
H00Q H 0.8965 0.6958 0.2835 0.026 Uiso 1 1 calc R U . . .
C00Q C 0.73691(16) 0.73392(13) 0.35432(8) 0.0234(3) Uani 1 1 d . . . . .
H00R H 0.6767 0.7699 0.3192 0.028 Uiso 1 1 calc R U . . .
C00R C 0.87284(15) 0.46290(13) 0.70696(7) 0.0214(3) Uani 1 1 d . . . . .
H00S H 0.9727 0.4498 0.7176 0.032 Uiso 1 1 calc R U . . .
H00T H 0.8349 0.3936 0.6810 0.032 Uiso 1 1 calc R U . . .
H00U H 0.8213 0.4741 0.7529 0.032 Uiso 1 1 calc R U . . .
C00S C 0.87166(16) 0.10047(14) 0.66547(8) 0.0240(3) Uani 1 1 d . . . . .
H00V H 0.9177 0.1141 0.7108 0.029 Uiso 1 1 calc R U . . .
C00T C 0.92649(16) 0.01066(13) 0.61931(8) 0.0252(3) Uani 1 1 d . . . . .
H00W H 1.0039 -0.0368 0.6345 0.030 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
O001 C00D 1.2304(17) . ?
N002 C00D 1.3625(18) . ?
N002 C00E 1.4613(16) . ?
N002 C00N 1.4642(17) . ?
N003 C004 1.3710(17) . ?
N003 C00S 1.3213(18) . ?
C004 C006 1.4306(18) . ?
C004 C007 1.4240(18) . ?
C005 C006 1.4998(18) . ?
C005 C008 1.4038(18) . ?
C005 C00L 1.4080(18) . ?
C006 C00A 1.3748(18) . ?
C007 C009 1.4179(19) . ?
C007 C00J 1.4181(19) . ?
C008 C00B 1.3926(18) . ?
C008 C00E 1.5190(19) . ?
C009 C00K 1.365(2) . ?
C00A C00K 1.4099(19) . ?
C00B C00H 1.391(2) . ?
C00C C00G 1.396(2) . ?
C00C C00Q 1.392(2) . ?
C00D C00R 1.510(2) . ?
C00F C00G 1.3928(19) . ?
C00F C00M 1.3921(19) . ?
C00G C00N 1.5171(18) . ?
C00H C00I 1.389(2) . ?
C00I C00L 1.3964(19) . ?
C00J C00T 1.364(2) . ?
C00L C00O 1.5028(19) . ?
C00M C00P 1.386(2) . ?
C00P C00Q 1.389(2) . ?
C00S C00T 1.414(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D N002 C00E 123.19(11) . . ?
C00D N002 C00N 119.59(11) . . ?
C00E N002 C00N 116.37(11) . . ?
C00S N003 C004 117.49(12) . . ?
N003 C004 C006 118.44(11) . . ?
N003 C004 C007 122.03(12) . . ?
C007 C004 C006 119.47(11) . . ?
C008 C005 C006 119.54(11) . . ?
C008 C005 C00L 119.88(12) . . ?
C00L C005 C006 120.52(12) . . ?
C004 C006 C005 121.69(11) . . ?
C00A C006 C004 118.28(12) . . ?
C00A C006 C005 119.98(12) . . ?
C009 C007 C004 119.93(12) . . ?
C009 C007 C00J 122.06(12) . . ?
C00J C007 C004 117.92(12) . . ?
C005 C008 C00E 119.00(11) . . ?
C00B C008 C005 119.91(12) . . ?
C00B C008 C00E 121.09(12) . . ?
C00K C009 C007 119.39(12) . . ?
C006 C00A C00K 121.91(13) . . ?
C00H C00B C008 120.34(13) . . ?
C00Q C00C C00G 120.60(13) . . ?
O001 C00D N002 121.96(13) . . ?
O001 C00D C00R 119.82(12) . . ?
N002 C00D C00R 118.19(12) . . ?
N002 C00E C008 114.47(11) . . ?
C00M C00F C00G 120.32(13) . . ?
C00C C00G C00N 119.40(12) . . ?
C00F C00G C00C 118.87(13) . . ?
C00F C00G C00N 121.68(12) . . ?
C00I C00H C00B 119.83(13) . . ?
C00H C00I C00L 120.99(13) . . ?
C00T C00J C007 119.34(13) . . ?
C009 C00K C00A 120.83(13) . . ?
C005 C00L C00O 121.22(12) . . ?
C00I C00L C005 119.03(13) . . ?
C00I C00L C00O 119.75(12) . . ?
C00P C00M C00F 120.54(13) . . ?
N002 C00N C00G 114.15(11) . . ?
C00M C00P C00Q 119.52(13) . . ?
C00P C00Q C00C 120.13(14) . . ?
N003 C00S C00T 124.42(14) . . ?
C00J C00T C00S 118.66(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_hxy_2_autored
_audit_block_doi                 10.5517/ccdc.csd.cc2kyd0y
_database_code_depnum_ccdc_archive 'CCDC 2381730'
loop_
_audit_author_name
_audit_author_address
'Ling Huang'
;Institute of Medicinal Biotechnology
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C21 H24 N2 O'
_chemical_formula_sum            'C21 H24 Cl2 N2 O'
_chemical_formula_weight         391.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H23ClN2O
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.90220(10)
_cell_length_b                   15.1936(2)
_cell_length_c                   16.9727(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2037.79(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22337
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7460
_cell_measurement_theta_min      2.6020
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.700
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.611
_diffrn_reflns_theta_min         3.905
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 115.00   0.50    0.05    --   45.56  77.00  30.00  182
  2  ω     61.00  99.00   0.50    0.05    --   45.56 148.00 -85.00   76
  3  ω     85.00 135.00   0.50    0.05    --  106.25 148.00 -85.00  100
  4  ω     84.00 172.00   0.50    0.05    --  106.25  77.00   0.00  176
  5  ω     89.00 116.00   0.50    0.05    --  106.25 124.00 109.00   54
  6  ω    119.00 166.00   0.50    0.05    --  106.25  19.00 -90.00   94
  7  ω     75.00 100.00   0.50    0.05    --  106.25 -99.00-120.00   50
  8  ω    100.00 127.00   0.50    0.05    --  106.25-148.00-134.00   54
  9  ω     45.00 111.00   0.50    0.05    --  106.25-125.00-150.00  132
 10  ω     67.00  99.00   0.50    0.05    --   45.56-148.00-134.00   64
 11  ω     17.00  86.00   0.50    0.05    --   45.56-125.00 -90.00  138
 12  ω     49.00  74.00   0.50    0.05    --  106.25-124.00  30.00   50
 13  ω     40.00  81.00   0.50    0.05    --  106.25-125.00  60.00   82
 14  ω     38.00  82.00   0.50    0.05    --  106.25 -99.00  60.00   88
 15  ω     86.00 111.00   0.50    0.05    --  106.25-125.00  30.00   50
 16  ω     79.00 104.00   0.50    0.05    --  106.25 -99.00 -90.00   50
 17  ω     41.00  98.00   0.50    0.05    --  106.25 -99.00-150.00  114
 18  ω     42.00  67.00   0.50    0.05    --  106.25 -99.00 -90.00   50
 19  ω    -25.00  21.00   0.50    0.05    --   45.56 -19.00   0.00   92
 20  ω    -24.00   2.00   0.50    0.05    --   45.56 -19.00  30.00   52
 21  ω    -27.00  16.00   0.50    0.05    --   45.56 -19.00  60.00   86
 22  ω    -21.00  22.00   0.50    0.05    --   45.56 -19.00  90.00   86
 23  ω    -95.00 -70.00   0.50    0.05    --  -45.56 148.00 -85.00   50
 24  ω   -124.00 -35.00   0.50    0.05    --  -97.00 148.00 -85.00  178
 25  ω   -126.00 -88.00   0.50    0.05    --  -97.00 144.00  43.18   76
 26  ω   -108.00 -80.00   0.50    0.05    --  -97.00 110.00  24.06   56
 27  ω   -108.00 -71.00   0.50    0.05    --  -97.00 109.00  43.67   74
 28  ω    -70.00 -45.00   0.50    0.05    --  -97.00 109.00  43.67   50
 29  ω    -57.00 -27.00   0.50    0.05    --  -97.00 110.00  24.06   60
 30  ω    -64.00 -37.00   0.50    0.05    --  -97.00 124.00 109.00   54
 31  ω   -102.00 -76.00   0.50    0.05    --  -97.00 124.00 109.00   52
 32  ω    -68.00 -24.00   0.50    0.05    --  -97.00  57.00 150.00   88
 33  ω    -68.00 -31.00   0.50    0.05    --  -97.00  57.00 120.00   74
 34  ω    -68.00 -24.00   0.50    0.05    --  -97.00  57.00 -30.00   88
 35  ω    -67.00 -41.00   0.50    0.05    --  -97.00  57.00 -60.00   52
 36  ω    -69.00 -31.00   0.50    0.05    --  -97.00  57.00 -90.00   76
 37  ω   -168.00 -83.00   0.50    0.05    --  -97.00 -57.00 -60.00  170
 38  ω   -132.00 -86.00   0.50    0.05    --  -97.00 -19.00-150.00   92
 39  ω   -168.00-130.00   0.50    0.05    --  -97.00 -57.00  30.00   76
 40  ω   -125.00 -84.00   0.50    0.05    --  -97.00 -57.00  30.00   82
 41  ω   -171.00-144.00   0.50    0.05    --  -97.00 -19.00-150.00   54
 42  ω   -122.00 -96.00   0.50    0.05    --  -97.00 -57.00 120.00   52
 43  ω   -168.00-143.00   0.50    0.05    --  -97.00 -57.00 120.00   50
 44  ω   -168.00-109.00   0.50    0.05    --  -97.00 -99.00  60.00  118
 45  ω   -166.00 -84.00   0.50    0.05    --  -97.00-125.00   0.00  164
 46  ω   -118.00 -68.00   0.50    0.05    --  -45.56-148.00-134.00  100
 47  ω   -148.00-121.00   0.50    0.05    --  -97.00-148.00-134.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0672200000
_diffrn_orient_matrix_UB_12      -0.0949644000
_diffrn_orient_matrix_UB_13      0.0055730000
_diffrn_orient_matrix_UB_21      -0.1823824000
_diffrn_orient_matrix_UB_22      0.0341271000
_diffrn_orient_matrix_UB_23      -0.0100445000
_diffrn_orient_matrix_UB_31      0.0163157000
_diffrn_orient_matrix_UB_32      -0.0095785000
_diffrn_orient_matrix_UB_33      -0.0900158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                4083
_reflns_number_total             4146
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.061
_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)+(0.0539P)²+0.4868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N005(H00A,H00B), C00G(H00E,H00G), C00J(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00F(H00F), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00R), C006(H006), C007(H007)
2.c Idealised Me refined as rotating group:
 C00O(H00O,H00P,H00Q), C00Q(H00S,H00T,H00U)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_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
Cl01 Cl 0.23486(6) 0.76941(3) 0.55044(3) 0.02264(13) Uani 1 1 d . . . . .
Cl02 Cl 0.17658(7) 0.38619(4) 0.31297(4) 0.03438(15) Uani 1 1 d . . . . .
O003 O 0.32618(19) 0.48121(11) 0.18790(9) 0.0255(3) Uani 1 1 d . . . . .
H003 H 0.269133 0.452480 0.220795 0.038 Uiso 1 1 calc R U . . .
N004 N 0.4847(2) 0.49643(12) 0.21766(10) 0.0204(3) Uani 1 1 d . . . . .
N005 N 0.4218(2) 0.61514(11) 0.47637(10) 0.0196(3) Uani 1 1 d . . . . .
H00A H 0.515945 0.637719 0.453077 0.024 Uiso 1 1 calc R U . . .
H00B H 0.354503 0.661218 0.490259 0.024 Uiso 1 1 calc R U . . .
C00A C 0.2694(3) 0.61861(13) 0.35027(12) 0.0196(4) Uani 1 1 d . . . . .
C00B C 0.0645(3) 0.72311(14) 0.30157(13) 0.0225(4) Uani 1 1 d . . . . .
H00C H -0.037201 0.755530 0.308699 0.027 Uiso 1 1 calc R U . . .
C00C C 0.1544(3) 0.73103(15) 0.23188(13) 0.0245(4) Uani 1 1 d . . . . .
H00D H 0.114734 0.769781 0.192025 0.029 Uiso 1 1 calc R U . . .
C00D C 0.6083(3) 0.43828(14) 0.19828(13) 0.0219(4) Uani 1 1 d . . . . .
C00E C 0.3565(3) 0.62508(14) 0.27882(12) 0.0203(4) Uani 1 1 d . . . . .
C00F C 0.1220(3) 0.66817(13) 0.36092(12) 0.0205(4) Uani 1 1 d . . . . .
H00F H 0.061149 0.664144 0.409053 0.025 Uiso 1 1 calc R U . . .
C00G C 0.4742(3) 0.56786(15) 0.54971(13) 0.0251(4) Uani 1 1 d . . . . .
H00E H 0.371406 0.549929 0.578915 0.030 Uiso 1 1 calc R U . . .
H00G H 0.538288 0.609119 0.583606 0.030 Uiso 1 1 calc R U . . .
C00H C 0.7691(3) 0.45489(14) 0.22753(12) 0.0228(4) Uani 1 1 d . . . . .
H00H H 0.858475 0.414999 0.216332 0.027 Uiso 1 1 calc R U . . .
C00I C 0.3024(3) 0.68292(14) 0.21935(13) 0.0239(4) Uani 1 1 d . . . . .
C00J C 0.3291(3) 0.56041(13) 0.41686(12) 0.0207(4) Uani 1 1 d . . . . .
H00I H 0.230788 0.531428 0.442066 0.025 Uiso 1 1 calc R U . . .
H00J H 0.404972 0.514071 0.396057 0.025 Uiso 1 1 calc R U . . .
C00K C 0.7265(3) 0.49189(15) 0.48792(13) 0.0280(5) Uani 1 1 d . . . . .
H00K H 0.757630 0.546025 0.463954 0.034 Uiso 1 1 calc R U . . .
C00L C 0.5408(3) 0.40870(16) 0.57148(13) 0.0286(5) Uani 1 1 d . . . . .
H00L H 0.442725 0.405292 0.603686 0.034 Uiso 1 1 calc R U . . .
C00M C 0.7829(3) 0.33895(15) 0.51304(15) 0.0328(5) Uani 1 1 d . . . . .
H00M H 0.850682 0.288057 0.505297 0.039 Uiso 1 1 calc R U . . .
C00N C 0.6412(3) 0.33477(15) 0.56160(15) 0.0333(5) Uani 1 1 d . . . . .
H00N H 0.613408 0.281461 0.587840 0.040 Uiso 1 1 calc R U . . .
C00O C 0.4023(3) 0.69306(18) 0.14447(14) 0.0339(5) Uani 1 1 d . . . . .
H00O H 0.405002 0.636735 0.116356 0.051 Uiso 1 1 calc R U . . .
H00P H 0.518126 0.711260 0.157169 0.051 Uiso 1 1 calc R U . . .
H00Q H 0.348950 0.737779 0.111095 0.051 Uiso 1 1 calc R U . . .
C00P C 0.8253(3) 0.41717(17) 0.47596(14) 0.0318(5) Uani 1 1 d . . . . .
H00R H 0.921490 0.419813 0.442473 0.038 Uiso 1 1 calc R U . . .
C00Q C 0.5620(3) 0.36237(16) 0.14735(15) 0.0313(5) Uani 1 1 d . . . . .
H00S H 0.471838 0.328308 0.172705 0.047 Uiso 1 1 calc R U . . .
H00T H 0.661327 0.324752 0.139585 0.047 Uiso 1 1 calc R U . . .
H00U H 0.522246 0.384031 0.096211 0.047 Uiso 1 1 calc R U . . .
C006 C 0.6693(3) 0.58644(14) 0.28998(12) 0.0223(4) Uani 1 1 d . . . . .
H006 H 0.690622 0.637727 0.320429 0.027 Uiso 1 1 calc R U . . .
C007 C 0.8009(3) 0.52851(14) 0.27263(12) 0.0230(4) Uani 1 1 d . . . . .
H007 H 0.911806 0.539691 0.291757 0.028 Uiso 1 1 calc R U . . .
C008 C 0.5082(3) 0.56922(14) 0.26291(12) 0.0197(4) Uani 1 1 d . . . . .
C009 C 0.5814(3) 0.48755(15) 0.53510(12) 0.0243(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O003 H003 0.8400 . ?
O003 N004 1.371(2) . ?
N004 C00D 1.357(3) . ?
N004 C008 1.359(3) . ?
N005 H00A 0.9100 . ?
N005 H00B 0.9100 . ?
N005 C00G 1.496(3) . ?
N005 C00J 1.499(3) . ?
C00A C00E 1.398(3) . ?
C00A C00F 1.398(3) . ?
C00A C00J 1.511(3) . ?
C00B H00C 0.9500 . ?
C00B C00C 1.385(3) . ?
C00B C00F 1.385(3) . ?
C00C H00D 0.9500 . ?
C00C C00I 1.395(3) . ?
C00D C00H 1.387(3) . ?
C00D C00Q 1.487(3) . ?
C00E C00I 1.405(3) . ?
C00E C008 1.493(3) . ?
C00F H00F 0.9500 . ?
C00G H00E 0.9900 . ?
C00G H00G 0.9900 . ?
C00G C009 1.506(3) . ?
C00H H00H 0.9500 . ?
C00H C007 1.378(3) . ?
C00I C00O 1.504(3) . ?
C00J H00I 0.9900 . ?
C00J H00J 0.9900 . ?
C00K H00K 0.9500 . ?
C00K C00P 1.393(3) . ?
C00K C009 1.400(3) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.385(3) . ?
C00L C009 1.385(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.392(4) . ?
C00M C00P 1.386(4) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?
C00P H00R 0.9500 . ?
C00Q H00S 0.9800 . ?
C00Q H00T 0.9800 . ?
C00Q H00U 0.9800 . ?
C006 H006 0.9500 . ?
C006 C007 1.394(3) . ?
C006 C008 1.378(3) . ?
C007 H007 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
N004 O003 H003 109.5 . . ?
C00D N004 O003 117.29(17) . . ?
C00D N004 C008 124.63(18) . . ?
C008 N004 O003 118.06(17) . . ?
H00A N005 H00B 107.5 . . ?
C00G N005 H00A 108.4 . . ?
C00G N005 H00B 108.4 . . ?
C00G N005 C00J 115.45(16) . . ?
C00J N005 H00A 108.4 . . ?
C00J N005 H00B 108.4 . . ?
C00E C00A C00F 118.98(19) . . ?
C00E C00A C00J 122.43(18) . . ?
C00F C00A C00J 118.59(18) . . ?
C00C C00B H00C 119.8 . . ?
C00F C00B H00C 119.8 . . ?
C00F C00B C00C 120.32(19) . . ?
C00B C00C H00D 119.5 . . ?
C00B C00C C00I 121.0(2) . . ?
C00I C00C H00D 119.5 . . ?
N004 C00D C00H 116.98(18) . . ?
N004 C00D C00Q 117.9(2) . . ?
C00H C00D C00Q 125.1(2) . . ?
C00A C00E C00I 121.13(19) . . ?
C00A C00E C008 120.82(18) . . ?
C00I C00E C008 118.04(18) . . ?
C00A C00F H00F 119.9 . . ?
C00B C00F C00A 120.26(19) . . ?
C00B C00F H00F 119.9 . . ?
N005 C00G H00E 108.7 . . ?
N005 C00G H00G 108.7 . . ?
N005 C00G C009 114.08(17) . . ?
H00E C00G H00G 107.6 . . ?
C009 C00G H00E 108.7 . . ?
C009 C00G H00G 108.7 . . ?
C00D C00H H00H 119.6 . . ?
C007 C00H C00D 120.89(19) . . ?
C007 C00H H00H 119.6 . . ?
C00C C00I C00E 118.3(2) . . ?
C00C C00I C00O 121.0(2) . . ?
C00E C00I C00O 120.73(19) . . ?
N005 C00J C00A 109.39(16) . . ?
N005 C00J H00I 109.8 . . ?
N005 C00J H00J 109.8 . . ?
C00A C00J H00I 109.8 . . ?
C00A C00J H00J 109.8 . . ?
H00I C00J H00J 108.2 . . ?
C00P C00K H00K 119.9 . . ?
C00P C00K C009 120.3(2) . . ?
C009 C00K H00K 119.9 . . ?
C00N C00L H00L 119.5 . . ?
C00N C00L C009 121.0(2) . . ?
C009 C00L H00L 119.5 . . ?
C00N C00M H00M 119.9 . . ?
C00P C00M H00M 119.9 . . ?
C00P C00M C00N 120.2(2) . . ?
C00L C00N C00M 119.7(2) . . ?
C00L C00N H00N 120.2 . . ?
C00M C00N H00N 120.2 . . ?
C00I C00O H00O 109.5 . . ?
C00I C00O H00P 109.5 . . ?
C00I C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
C00K C00P H00R 120.1 . . ?
C00M C00P C00K 119.8(2) . . ?
C00M C00P H00R 120.1 . . ?
C00D C00Q H00S 109.5 . . ?
C00D C00Q H00T 109.5 . . ?
C00D C00Q H00U 109.5 . . ?
H00S C00Q H00T 109.5 . . ?
H00S C00Q H00U 109.5 . . ?
H00T C00Q H00U 109.5 . . ?
C007 C006 H006 120.0 . . ?
C008 C006 H006 120.0 . . ?
C008 C006 C007 119.90(19) . . ?
C00H C007 C006 119.6(2) . . ?
C00H C007 H007 120.2 . . ?
C006 C007 H007 120.2 . . ?
N004 C008 C00E 117.06(18) . . ?
N004 C008 C006 117.97(19) . . ?
C006 C008 C00E 124.97(18) . . ?
C00K C009 C00G 121.1(2) . . ?
C00L C009 C00G 119.8(2) . . ?
C00L C009 C00K 119.0(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O003 H003 Cl02 0.84 2.00 2.8264(17) 168.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O003 N004 C00D C00H 178.95(18) . . . . ?
O003 N004 C00D C00Q -0.7(3) . . . . ?
O003 N004 C008 C00E 2.2(3) . . . . ?
O003 N004 C008 C006 -177.27(18) . . . . ?
N004 C00D C00H C007 -1.5(3) . . . . ?
N005 C00G C009 C00K 51.9(3) . . . . ?
N005 C00G C009 C00L -130.9(2) . . . . ?
C00A C00E C00I C00C -2.9(3) . . . . ?
C00A C00E C00I C00O 176.6(2) . . . . ?
C00A C00E C008 N004 100.0(2) . . . . ?
C00A C00E C008 C006 -80.6(3) . . . . ?
C00B C00C C00I C00E 1.0(3) . . . . ?
C00B C00C C00I C00O -178.6(2) . . . . ?
C00C C00B C00F C00A -1.5(3) . . . . ?
C00D N004 C008 C00E -179.29(19) . . . . ?
C00D N004 C008 C006 1.3(3) . . . . ?
C00D C00H C007 C006 0.9(3) . . . . ?
C00E C00A C00F C00B -0.4(3) . . . . ?
C00E C00A C00J N005 99.2(2) . . . . ?
C00F C00A C00E C00I 2.6(3) . . . . ?
C00F C00A C00E C008 -176.14(19) . . . . ?
C00F C00A C00J N005 -80.4(2) . . . . ?
C00F C00B C00C C00I 1.2(3) . . . . ?
C00G N005 C00J C00A 174.39(16) . . . . ?
C00I C00E C008 N004 -78.8(3) . . . . ?
C00I C00E C008 C006 100.6(3) . . . . ?
C00J N005 C00G C009 56.0(2) . . . . ?
C00J C00A C00E C00I -176.95(19) . . . . ?
C00J C00A C00E C008 4.3(3) . . . . ?
C00J C00A C00F C00B 179.21(18) . . . . ?
C00N C00L C009 C00G -177.4(2) . . . . ?
C00N C00L C009 C00K -0.1(3) . . . . ?
C00N C00M C00P C00K 0.5(4) . . . . ?
C00P C00K C009 C00G 179.1(2) . . . . ?
C00P C00K C009 C00L 1.9(3) . . . . ?
C00P C00M C00N C00L 1.3(4) . . . . ?
C00Q C00D C00H C007 178.2(2) . . . . ?
C007 C006 C008 N004 -1.9(3) . . . . ?
C007 C006 C008 C00E 178.74(19) . . . . ?
C008 N004 C00D C00H 0.4(3) . . . . ?
C008 N004 C00D C00Q -179.3(2) . . . . ?
C008 C00E C00I C00C 175.88(19) . . . . ?
C008 C00E C00I C00O -4.6(3) . . . . ?
C008 C006 C007 C00H 0.9(3) . . . . ?
C009 C00K C00P C00M -2.1(4) . . . . ?
C009 C00L C00N C00M -1.5(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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.630
####################################################################### 
# 
# 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_hxy-5_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kyd31
_database_code_depnum_ccdc_archive 'CCDC 2381733'
loop_
_audit_author_name
_audit_author_address
'Ling Huang'
;Institute of Medicinal Biotechnology
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-08-19
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C20 H21 N2 O'
_chemical_formula_sum            'C20 H22 Cl2 N2 O'
_chemical_formula_weight         377.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8488(3)
_cell_length_b                   15.7366(5)
_cell_length_c                   15.8854(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1962.06(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4539
_cell_measurement_temperature    295.24(10)
_cell_measurement_theta_max      72.4570
_cell_measurement_theta_min      5.5360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.234
_diffrn_reflns_theta_min         3.954
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.24(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -32.00   0.50    0.16    -- -103.00 125.00 -60.00  134
  2  ω    -97.00 -42.00   0.50    0.16    -- -103.00 117.00-169.00  110
  3  ω    -72.00 -32.00   0.50    0.05    --  -43.34 117.00-169.00   80
  4  ω    -10.00  24.00   0.50    0.05    --  -43.34  38.00 -30.00   68
  5  ω    -11.00  32.00   0.50    0.05    --  -43.34  38.00   0.00   86
  6  ω     97.00 133.00   0.50    0.16    --  107.48  15.00 120.00   72
  7  ω     97.00 137.00   0.50    0.16    --  107.48  15.00  30.00   80
  8  ω    106.00 164.00   0.50    0.16    --  107.48  77.00 -60.00  116
  9  ω    120.00 146.00   0.50    0.16    --  107.48 117.00-169.00   52
 10  ω    -32.00  22.00   0.50    0.05    --   43.34 -38.00-180.00  108
 11  ω     35.00  64.00   0.50    0.16    --  107.48 -77.00-180.00   58
 12  ω     48.00  77.00   0.50    0.16    --  107.48 -77.00  30.00   58
 13  ω     33.00  74.00   0.50    0.16    --  107.48 -77.00  90.00   82
 14  ω     38.00  75.00   0.50    0.16    --  107.48 -77.00 120.00   74
 15  ω     35.00  64.00   0.50    0.16    --  107.48 -77.00 150.00   58
 16  ω     43.00  74.00   0.50    0.16    --  107.48 -77.00 -90.00   62
 17  ω     37.00 101.00   0.50    0.16    --  107.48-125.00 -60.00  128
 18  ω     64.00  98.00   0.50    0.16    --  107.48-117.00 103.00   68
 19  ω     14.00  69.00   0.50    0.05    --   43.34-117.00 103.00  110
 20  ω   -133.00 -95.00   0.50    0.16    -- -103.00 -15.00 150.00   76
 21  ω   -136.00 -94.00   0.50    0.16    -- -103.00-117.00 103.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0243789000
_diffrn_orient_matrix_UB_12      -0.0541197000
_diffrn_orient_matrix_UB_13      0.0798947000
_diffrn_orient_matrix_UB_21      0.0840522000
_diffrn_orient_matrix_UB_22      -0.0704749000
_diffrn_orient_matrix_UB_23      -0.0530076000
_diffrn_orient_matrix_UB_31      0.1757414000
_diffrn_orient_matrix_UB_32      0.0411252000
_diffrn_orient_matrix_UB_33      0.0143028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3384
_reflns_number_total             3909
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.067
_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)+(0.1184P)²+0.1862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O15) = Uanis(O15A)
3. Others
 Sof(O15A)=1-FVAR(1)
 Sof(O15)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 N17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C10(H10), C13(H13), C12(H12), C11(H11), C20(H20),
 C22(H22), C23(H23), C24(H24), C21(H21)
4.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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 0.88311(16) 0.72924(7) 0.40843(7) 0.0660(4) Uani 1 1 d . . . . .
Cl2 Cl 0.7785(3) 0.35178(14) 0.62693(14) 0.1152(7) Uani 1 1 d . . . . .
N17 N 0.6184(5) 0.6356(2) 0.5151(2) 0.0496(7) Uani 1 1 d . . . . .
H17A H 0.693005 0.673482 0.495724 0.060 Uiso 1 1 calc R U . . .
H17B H 0.538720 0.663996 0.543350 0.060 Uiso 1 1 calc R U . . .
N14 N 0.5632(5) 0.4837(2) 0.7548(3) 0.0604(9) Uani 1 1 d . . . . .
O15 O 0.7306(7) 0.4593(4) 0.7627(5) 0.079(2) Uani 0.91(2) 1 d . . P A 2
C8 C 0.7680(5) 0.6267(3) 0.6502(3) 0.0504(8) Uani 1 1 d . . . . .
C16 C 0.7079(6) 0.5778(3) 0.5746(3) 0.0548(10) Uani 1 1 d . . . . .
H16A H 0.804672 0.551816 0.546602 0.066 Uiso 1 1 calc R U . . .
H16B H 0.631205 0.532873 0.592251 0.066 Uiso 1 1 calc R U . . .
C9 C 0.5302(6) 0.5665(3) 0.7370(3) 0.0526(9) Uani 1 1 d . . . . .
C19 C 0.4174(6) 0.5226(3) 0.4657(3) 0.0539(9) Uani 1 1 d . . . . .
C3 C 0.6789(5) 0.6243(3) 0.7265(2) 0.0496(9) Uani 1 1 d . . . . .
C7 C 0.9117(6) 0.6783(3) 0.6438(3) 0.0558(10) Uani 1 1 d . . . . .
H7 H 0.972252 0.680633 0.593524 0.067 Uiso 1 1 calc R U . . .
C6 C 0.9649(6) 0.7263(3) 0.7125(3) 0.0612(10) Uani 1 1 d . . . . .
H6 H 1.061754 0.760061 0.708299 0.073 Uiso 1 1 calc R U . . .
C18 C 0.5360(7) 0.5927(3) 0.4415(3) 0.0640(12) Uani 1 1 d . . . . .
H18A H 0.473387 0.634675 0.409333 0.077 Uiso 1 1 calc R U . . .
H18B H 0.624297 0.569666 0.405372 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7302(7) 0.6744(3) 0.7951(3) 0.0592(10) Uani 1 1 d . . . . .
C5 C 0.8755(6) 0.7240(3) 0.7858(3) 0.0602(10) Uani 1 1 d . . . . .
H5 H 0.912681 0.756650 0.831038 0.072 Uiso 1 1 calc R U . . .
C10 C 0.3627(7) 0.5898(3) 0.7313(4) 0.0691(13) Uani 1 1 d . . . . .
H10 H 0.335747 0.646186 0.719854 0.083 Uiso 1 1 calc R U . . .
C13 C 0.4412(8) 0.4255(4) 0.7653(4) 0.0758(14) Uani 1 1 d . . . . .
H13 H 0.470563 0.369460 0.776999 0.091 Uiso 1 1 calc R U . . .
C12 C 0.2732(8) 0.4479(4) 0.7589(4) 0.0748(14) Uani 1 1 d . . . . .
H12 H 0.187757 0.407508 0.765795 0.090 Uiso 1 1 calc R U . . .
C11 C 0.2330(7) 0.5320(4) 0.7420(4) 0.0778(15) Uani 1 1 d . . . . .
H11 H 0.119827 0.549067 0.737882 0.093 Uiso 1 1 calc R U . . .
C20 C 0.4591(9) 0.4407(4) 0.4460(4) 0.0785(15) Uani 1 1 d . . . . .
H20 H 0.561135 0.429256 0.418429 0.094 Uiso 1 1 calc R U . . .
C22 C 0.2030(10) 0.3898(5) 0.5090(4) 0.0905(19) Uani 1 1 d . . . . .
H22 H 0.131577 0.345217 0.524056 0.109 Uiso 1 1 calc R U . . .
C23 C 0.1599(8) 0.4693(5) 0.5290(5) 0.0940(19) Uani 1 1 d . . . . .
H23 H 0.058347 0.479567 0.557469 0.113 Uiso 1 1 calc R U . . .
C24 C 0.2666(8) 0.5377(4) 0.5076(5) 0.0886(18) Uani 1 1 d . . . . .
H24 H 0.235572 0.592972 0.521566 0.106 Uiso 1 1 calc R U . . .
C25 C 0.6318(9) 0.6739(5) 0.8762(3) 0.0830(16) Uani 1 1 d . . . . .
H25A H 0.523976 0.701402 0.867987 0.125 Uiso 1 1 calc R U . . .
H25B H 0.695237 0.703557 0.918723 0.125 Uiso 1 1 calc R U . . .
H25C H 0.613364 0.616228 0.893854 0.125 Uiso 1 1 calc R U . . .
C21 C 0.3483(12) 0.3733(4) 0.4672(5) 0.099(2) Uani 1 1 d . . . . .
H21 H 0.375720 0.317801 0.452341 0.119 Uiso 1 1 calc R U . . .
O15A O 0.709(7) 0.486(4) 0.802(6) 0.079(2) Uani 0.09(2) 1 d . . 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
N17 H17A 0.8900 . ?
N17 H17B 0.8900 . ?
N17 C16 1.489(5) . ?
N17 C18 1.496(6) . ?
N14 O15 1.374(7) . ?
N14 C9 1.359(6) . ?
N14 C13 1.336(7) . ?
N14 O15A 1.36(6) . ?
C8 C16 1.503(6) . ?
C8 C3 1.400(6) . ?
C8 C7 1.394(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C9 C3 1.489(6) . ?
C9 C10 1.368(7) . ?
C19 C18 1.493(7) . ?
C19 C20 1.367(7) . ?
C19 C24 1.378(8) . ?
C3 C4 1.405(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.391(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.360(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C4 C5 1.390(7) . ?
C4 C25 1.502(7) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.376(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.369(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.387(8) . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.412(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.335(11) . ?
C22 C21 1.345(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.406(10) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C21 H21 0.9300 . ?

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
H17A N17 H17B 107.5 . . ?
C16 N17 H17A 108.5 . . ?
C16 N17 H17B 108.5 . . ?
C16 N17 C18 115.0(3) . . ?
C18 N17 H17A 108.5 . . ?
C18 N17 H17B 108.5 . . ?
C9 N14 O15 118.0(4) . . ?
C9 N14 O15A 104(3) . . ?
C13 N14 O15 118.8(5) . . ?
C13 N14 C9 123.2(5) . . ?
C13 N14 O15A 123(2) . . ?
C3 C8 C16 121.4(4) . . ?
C7 C8 C16 119.6(4) . . ?
C7 C8 C3 118.9(4) . . ?
N17 C16 C8 110.0(3) . . ?
N17 C16 H16A 109.7 . . ?
N17 C16 H16B 109.7 . . ?
C8 C16 H16A 109.7 . . ?
C8 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N14 C9 C3 117.4(4) . . ?
N14 C9 C10 117.0(4) . . ?
C10 C9 C3 125.6(4) . . ?
C20 C19 C18 119.2(5) . . ?
C20 C19 C24 118.6(5) . . ?
C24 C19 C18 122.2(5) . . ?
C8 C3 C9 120.3(4) . . ?
C8 C3 C4 120.9(4) . . ?
C4 C3 C9 118.7(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
N17 C18 H18A 108.8 . . ?
N17 C18 H18B 108.8 . . ?
C19 C18 N17 113.7(4) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C3 C4 C25 121.0(5) . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 C25 121.1(5) . . ?
C6 C5 C4 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.7(5) . . ?
C11 C10 H10 119.1 . . ?
N14 C13 H13 119.8 . . ?
N14 C13 C12 120.3(5) . . ?
C12 C13 H13 119.8 . . ?
C13 C12 H12 120.7 . . ?
C13 C12 C11 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C10 C11 C12 119.1(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C23 C22 H22 119.5 . . ?
C23 C22 C21 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.5(7) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.8(6) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.7(6) . . ?
C22 C21 H21 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
N14 C9 C3 C8 80.9(5) . . . . ?
N14 C9 C3 C4 -97.4(5) . . . . ?
N14 C9 C10 C11 -0.8(8) . . . . ?
N14 C13 C12 C11 -0.4(9) . . . . ?
O15 N14 C9 C3 0.6(7) . . . . ?
O15 N14 C9 C10 -178.6(6) . . . . ?
O15 N14 C13 C12 179.2(7) . . . . ?
C8 C3 C4 C5 -2.2(6) . . . . ?
C8 C3 C4 C25 178.2(5) . . . . ?
C8 C7 C6 C5 -0.9(7) . . . . ?
C16 N17 C18 C19 53.8(6) . . . . ?
C16 C8 C3 C9 5.7(6) . . . . ?
C16 C8 C3 C4 -176.0(4) . . . . ?
C16 C8 C7 C6 177.6(4) . . . . ?
C9 N14 C13 C12 -0.5(9) . . . . ?
C9 C3 C4 C5 176.1(4) . . . . ?
C9 C3 C4 C25 -3.4(7) . . . . ?
C9 C10 C11 C12 -0.1(10) . . . . ?
C19 C20 C21 C22 -1.7(11) . . . . ?
C3 C8 C16 N17 100.9(4) . . . . ?
C3 C8 C7 C6 0.1(6) . . . . ?
C3 C9 C10 C11 -179.9(5) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C7 C8 C16 N17 -76.6(5) . . . . ?
C7 C8 C3 C9 -176.8(4) . . . . ?
C7 C8 C3 C4 1.5(6) . . . . ?
C7 C6 C5 C4 0.2(7) . . . . ?
C18 N17 C16 C8 -173.7(4) . . . . ?
C18 C19 C20 C21 -179.2(6) . . . . ?
C18 C19 C24 C23 -179.8(6) . . . . ?
C10 C9 C3 C8 -100.0(6) . . . . ?
C10 C9 C3 C4 81.7(6) . . . . ?
C13 N14 C9 C3 -179.7(4) . . . . ?
C13 N14 C9 C10 1.1(7) . . . . ?
C13 C12 C11 C10 0.7(10) . . . . ?
C20 C19 C18 N17 -112.5(5) . . . . ?
C20 C19 C24 C23 0.1(10) . . . . ?
C22 C23 C24 C19 -0.3(12) . . . . ?
C23 C22 C21 C20 1.6(11) . . . . ?
C24 C19 C18 N17 67.4(7) . . . . ?
C24 C19 C20 C21 0.9(9) . . . . ?
C25 C4 C5 C6 -179.1(5) . . . . ?
C21 C22 C23 C24 -0.6(12) . . . . ?
O15A N14 C9 C3 33(4) . . . . ?
O15A N14 C9 C10 -147(4) . . . . ?
O15A N14 C13 C12 141(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 1.937
_oxdiff_exptl_absorpt_empirical_full_min 0.457
####################################################################### 
# 
# 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_hxy6-7
_audit_block_doi                 10.5517/ccdc.csd.cc2kyd20
_database_code_depnum_ccdc_archive 'CCDC 2381732'
loop_
_audit_author_name
_audit_author_address
'Ling Huang'
;Institute of Medicinal Biotechnology
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_audit_creation_date             2024-07-11
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'Cl, 0.5(C20 H20 F N2 O), 0.5(C20 H21 F N2 O1.5)'
_chemical_formula_sum            'C20 H20.50 Cl F N2 O1.25'
_chemical_formula_weight         363.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl F'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2259(2)
_cell_length_b                   19.4327(3)
_cell_length_c                   10.2890(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.079(3)
_cell_angle_gamma                90
_cell_volume                     1820.47(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3390
_cell_measurement_theta_min      4.5270
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             762
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17287
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.989
_diffrn_reflns_theta_min         4.551
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  92.00   0.50    0.18    --  107.48 -95.00-150.00  118
  2  ω     36.00 101.00   0.50    0.18    --  107.48-125.00 -30.00  130
  3  ω     36.00 101.00   0.50    0.18    --  107.48-125.00  30.00  130
  4  ω      6.00  80.00   0.50    0.05    --   43.09-108.00 127.00  148
  5  ω     35.00  93.00   0.50    0.18    --  107.48-108.00 127.00  116
  6  ω     33.00  78.00   0.50    0.18    --  107.48 -77.00  60.00   90
  7  ω     33.00  78.00   0.50    0.18    --  107.48 -77.00 120.00   90
  8  ω    -34.00  22.00   0.50    0.05    --   43.09 -38.00  30.00  112
  9  ω    -34.00  22.00   0.50    0.05    --   43.09 -38.00 -60.00  112
 10  ω     33.00  78.00   0.50    0.18    --  107.48 -77.00   0.00   90
 11  ω     33.00  78.00   0.50    0.18    --  107.48 -77.00 -90.00   90
 12  ω     93.00 139.00   0.50    0.18    --  107.48  15.00-180.00   92
 13  ω    -16.00  34.00   0.50    0.05    --  -43.09  38.00-180.00  100
 14  ω    -16.00  34.00   0.50    0.05    --  -43.09  38.00-150.00  100
 15  ω     93.00 139.00   0.50    0.18    --  107.48  15.00 150.00   92
 16  ω    104.00 175.00   0.50    0.18    --  107.48 108.00-135.00  142
 17  ω    -16.00  34.00   0.50    0.05    --  -43.09  38.00 -60.00  100
 18  ω    -80.00   0.00   0.50    0.05    --  -43.09 108.00-135.00  160
 19  ω    -92.00 -30.00   0.50    0.18    -- -103.00 108.00-135.00  124
 20  ω   -100.00 -31.00   0.50    0.18    -- -103.00 125.00 120.00  138
 21  ω   -120.00 -29.00   0.50    0.05    --  -43.09 -38.00-120.00  182
 22  ω   -163.00 -89.00   0.50    0.18    -- -103.00 -30.00  30.00  148
 23  ω   -174.00 -89.00   0.50    0.18    -- -103.00 -45.00  60.00  170
 24  ω   -174.00 -89.00   0.50    0.18    -- -103.00 -45.00  60.00  170
 25  ω   -133.00 -88.00   0.50    0.18    -- -103.00 -15.00-180.00   90
 26  ω   -120.00 -68.00   0.50    0.05    --  -43.09 -38.00  60.00  104
 27  ω   -174.00 -98.00   0.50    0.18    -- -103.00-108.00 127.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0409199000
_diffrn_orient_matrix_UB_12      -0.0768519000
_diffrn_orient_matrix_UB_13      0.0110097000
_diffrn_orient_matrix_UB_21      0.0825556000
_diffrn_orient_matrix_UB_22      0.0061335000
_diffrn_orient_matrix_UB_23      0.1675849000
_diffrn_orient_matrix_UB_31      -0.1418040000
_diffrn_orient_matrix_UB_32      -0.0186387000
_diffrn_orient_matrix_UB_33      0.0093480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                6291
_reflns_number_total             6613
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.3789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(N3B)=Sof(C37B)=Sof(H37B)=1-FVAR(1)
 Sof(C37A)=Sof(H37A)=Sof(N3A)=FVAR(1)
 Fixed Sof: O2B(0.5) O2A(0.5) O2(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2C,H2D), C28(H28A,H28B), C7(H7A,H7B), C8(H8A,H8B), C27(H27A,
 H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C20(H20), C10(H10), C17(H17), C4(H4), C11(H11), C12(H12), C3(H3),
 C37(H37), C25(H25), C1(H1), C30(H30), C32(H32), C40(H40), C18(H18), C39(H39),
 C31(H31), C23(H23), C22(H22), C21(H21), C24(H24), C37B(H37B), C37A(H37A)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C)
;
_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
Cl1 Cl -0.20832(7) 0.46949(4) 0.36370(9) 0.03358(18) Uani 1 1 d . . . . .
Cl2 Cl 0.75290(8) 0.61568(5) 0.72504(9) 0.0392(2) Uani 1 1 d . . . . .
F1 F 0.5806(2) 0.76741(12) 0.8637(2) 0.0442(5) Uani 1 1 d . . . . .
O1 O 0.2782(2) 0.60928(12) 0.5235(2) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.3003(3) 0.67320(13) 0.5754(3) 0.0242(5) Uani 1 1 d . . . . .
F2 F -0.0192(2) 0.29319(14) 0.1391(3) 0.0582(7) Uani 1 1 d . . . . .
N4 N 0.4964(3) 0.53203(14) 0.4942(3) 0.0268(5) Uani 1 1 d . . . . .
H4A H 0.570491 0.559390 0.556903 0.032 Uiso 1 1 calc R U . . .
H4B H 0.416357 0.540105 0.508663 0.032 Uiso 1 1 calc R U . . .
N2 N 0.0343(3) 0.56775(13) 0.5546(3) 0.0249(5) Uani 1 1 d . . . . .
H2C H 0.119601 0.569742 0.547209 0.030 Uiso 1 1 calc R U . . .
H2D H -0.024288 0.535869 0.489285 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3389(3) 0.55427(17) 0.8688(4) 0.0310(7) Uani 1 1 d . . . . .
H5 H 0.352381 0.512975 0.826909 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1950(3) 0.72240(16) 0.5087(3) 0.0256(6) Uani 1 1 d . . . . .
C20 C 0.4280(3) 0.68863(17) 0.6932(3) 0.0280(6) Uani 1 1 d . . . . .
H20 H 0.501662 0.654485 0.737406 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0448(3) 0.66042(16) 0.3713(3) 0.0261(6) Uani 1 1 d . . . . .
C28 C 0.5411(3) 0.45841(17) 0.5298(3) 0.0283(6) Uani 1 1 d . . . . .
H28A H 0.641955 0.452431 0.541294 0.034 Uiso 1 1 calc R U . . .
H28B H 0.474680 0.429066 0.447533 0.034 Uiso 1 1 calc R U . . .
C10 C -0.1595(3) 0.63936(17) 0.2396(3) 0.0299(6) Uani 1 1 d . . . . .
H10 H -0.234455 0.610341 0.239035 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0687(3) 0.54378(17) 0.7056(3) 0.0289(6) Uani 1 1 d . . . . .
H7A H 0.089026 0.493748 0.713187 0.035 Uiso 1 1 calc R U . . .
H7B H -0.018191 0.551427 0.722364 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1986(3) 0.58072(17) 0.8217(3) 0.0285(6) Uani 1 1 d . . . . .
C17 C 0.2180(3) 0.78770(17) 0.5675(3) 0.0310(7) Uani 1 1 d . . . . .
H17 H 0.144124 0.821709 0.523030 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4499(3) 0.75388(19) 0.7478(3) 0.0335(7) Uani 1 1 d . . . . .
C15 C 0.0657(3) 0.70287(16) 0.3707(3) 0.0259(6) Uani 1 1 d . . . . .
C4 C 0.4599(4) 0.58763(19) 0.9766(4) 0.0361(7) Uani 1 1 d . . . . .
H4 H 0.555336 0.568688 1.009392 0.043 Uiso 1 1 calc R U . . .
C11 C -0.1642(3) 0.66083(17) 0.1087(3) 0.0313(7) Uani 1 1 d . . . . .
H11 H -0.241242 0.645511 0.018677 0.038 Uiso 1 1 calc R U . . .
C12 C -0.0570(3) 0.70444(18) 0.1089(3) 0.0305(7) Uani 1 1 d . . . . .
H12 H -0.062827 0.719419 0.018574 0.037 Uiso 1 1 calc R U . . .
C29 C 0.5368(3) 0.43475(16) 0.6683(3) 0.0285(6) Uani 1 1 d . . . . .
C3 C 0.4412(4) 0.64819(19) 1.0358(4) 0.0348(7) Uani 1 1 d . . . . .
H3 H 0.524086 0.671230 1.108718 0.042 Uiso 1 1 calc R U . . .
C35 C 0.4247(4) 0.39077(16) 0.6598(3) 0.0296(6) Uani 1 1 d . . . . .
C37 C 0.3022(4) 0.6755(2) 0.9894(4) 0.0394(8) Uani 1 1 d . . . . .
H37 H 0.289515 0.717498 1.029544 0.047 Uiso 1 1 calc R U . . .
N3B N 0.3311(9) 0.3036(9) 0.4700(19) 0.028(3) Uani 0.47(5) 1 d . . P A 2
C8 C -0.0397(3) 0.63629(16) 0.5131(3) 0.0275(6) Uani 1 1 d . . . . .
H8A H 0.014707 0.670160 0.591068 0.033 Uiso 1 1 calc R U . . .
H8B H -0.140778 0.632690 0.502103 0.033 Uiso 1 1 calc R U . . .
C26 C 0.3252(4) 0.51588(19) 0.2282(3) 0.0319(7) Uani 1 1 d . . . . .
C25 C 0.1856(4) 0.54251(19) 0.1897(4) 0.0351(7) Uani 1 1 d . . . . .
H25 H 0.175217 0.583026 0.235890 0.042 Uiso 1 1 calc R U . . .
C13 C 0.0592(3) 0.72689(17) 0.2389(3) 0.0282(6) Uani 1 1 d . . . . .
C33 C 0.4226(4) 0.36527(18) 0.7866(4) 0.0391(8) Uani 1 1 d . . . . .
C1 C 0.1814(3) 0.6413(2) 0.8839(4) 0.0351(7) Uani 1 1 d . . . . .
H1 H 0.085788 0.659606 0.853736 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1748(4) 0.7742(2) 0.2366(4) 0.0422(9) Uani 1 1 d . . . . .
H14A H 0.168911 0.818996 0.277287 0.063 Uiso 1 1 calc R U . . .
H14B H 0.158555 0.780190 0.135721 0.063 Uiso 1 1 calc R U . . .
H14C H 0.272260 0.754170 0.295112 0.063 Uiso 1 1 calc R U . . .
C36 C 0.3042(4) 0.36979(18) 0.5164(4) 0.0306(7) Uani 1 1 d . . . . .
C30 C 0.6462(4) 0.45428(18) 0.8042(4) 0.0340(7) Uani 1 1 d . . . . .
H30 H 0.722546 0.484233 0.811183 0.041 Uiso 1 1 calc R U . . .
C32 C 0.5336(5) 0.3856(2) 0.9199(4) 0.0430(9) Uani 1 1 d . . . . .
H32 H 0.534085 0.368710 1.006718 0.052 Uiso 1 1 calc R U . . .
C40 C 0.1674(4) 0.39878(18) 0.4549(4) 0.0387(8) Uani 1 1 d . . . . .
H40 H 0.149216 0.436664 0.502725 0.046 Uiso 1 1 calc R U . . .
C18 C 0.3471(4) 0.80481(19) 0.6904(4) 0.0358(7) Uani 1 1 d . . . . .
H18 H 0.362953 0.849507 0.732248 0.043 Uiso 1 1 calc R U . . .
C27 C 0.4604(4) 0.55197(19) 0.3396(4) 0.0335(7) Uani 1 1 d . . . . .
H27A H 0.444927 0.602338 0.328212 0.040 Uiso 1 1 calc R U . . .
H27B H 0.544867 0.540481 0.321234 0.040 Uiso 1 1 calc R U . . .
C39 C 0.0541(4) 0.37509(19) 0.3252(4) 0.0374(7) Uani 1 1 d . . . . .
H39 H -0.039996 0.396253 0.281694 0.045 Uiso 1 1 calc R U . . .
C31 C 0.6437(4) 0.4298(2) 0.9308(4) 0.0419(8) Uani 1 1 d . . . . .
H31 H 0.717649 0.443466 1.024028 0.050 Uiso 1 1 calc R U . . .
C38 C 0.0864(4) 0.3198(2) 0.2647(4) 0.0414(9) Uani 1 1 d . . . . .
C23 C 0.0753(4) 0.4512(2) 0.0170(4) 0.0430(9) Uani 1 1 d . . . . .
H23 H -0.009694 0.429084 -0.054873 0.052 Uiso 1 1 calc R U . . .
C22 C 0.2135(5) 0.4245(2) 0.0545(4) 0.0484(10) Uani 1 1 d . . . . .
H22 H 0.223420 0.383643 0.009178 0.058 Uiso 1 1 calc R U . . .
C21 C 0.3368(4) 0.4573(2) 0.1579(4) 0.0448(9) Uani 1 1 d . . . . .
H21 H 0.431264 0.439360 0.181081 0.054 Uiso 1 1 calc R U . . .
C24 C 0.0620(4) 0.5101(2) 0.0846(4) 0.0401(8) Uani 1 1 d . . . . .
H24 H -0.032585 0.528695 0.058808 0.048 Uiso 1 1 calc R U . . .
C34 C 0.3043(5) 0.3165(2) 0.7773(5) 0.0513(10) Uani 1 1 d . . . . .
H34A H 0.210181 0.340892 0.738576 0.077 Uiso 1 1 calc R U . . .
H34B H 0.328820 0.298698 0.874830 0.077 Uiso 1 1 calc R U . . .
H34C H 0.296802 0.278141 0.712418 0.077 Uiso 1 1 calc R U . . .
C37B C 0.2219(12) 0.2779(10) 0.346(2) 0.033(3) Uani 0.47(5) 1 d . . P A 2
H37B H 0.231286 0.233827 0.311298 0.040 Uiso 0.47(5) 1 calc R U P A 2
O2B O 0.4537(6) 0.2712(3) 0.5338(7) 0.0441(13) Uani 0.5 1 d . . P A 2
O2A O 0.4625(5) 0.3074(4) 0.4708(7) 0.0443(13) Uani 0.5 1 d . . P A 1
C37A C 0.2187(11) 0.3017(13) 0.302(2) 0.037(4) Uani 0.53(5) 1 d . . P A 1
H37A H 0.240298 0.270928 0.242174 0.044 Uiso 0.53(5) 1 calc R U P A 1
N3A N 0.3285(9) 0.3271(11) 0.428(2) 0.032(3) Uani 0.53(5) 1 d . . P A 1
O2 O 0.4111(8) 0.1959(4) 0.5993(8) 0.0639(17) Uiso 0.5 1 d G . P . .
H2A H 0.453165 0.226799 0.569819 0.096 Uiso 0.5 1 d G U P A 1
H2B H 0.336959 0.181569 0.519787 0.096 Uiso 0.5 1 d G 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
F1 C19 1.352(4) . ?
O1 N1 1.330(3) . ?
N1 C16 1.368(4) . ?
N1 C20 1.350(4) . ?
F2 C38 1.354(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C28 1.496(4) . ?
N4 C27 1.510(4) . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
N2 C7 1.502(4) . ?
N2 C8 1.495(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(4) . ?
C5 C4 1.390(5) . ?
C16 C17 1.379(5) . ?
C16 C15 1.483(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.364(5) . ?
C9 C10 1.390(4) . ?
C9 C15 1.402(4) . ?
C9 C8 1.510(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.516(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.504(4) . ?
C6 C1 1.389(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(5) . ?
C19 C18 1.367(5) . ?
C15 C13 1.407(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(4) . ?
C29 C35 1.400(5) . ?
C29 C30 1.388(5) . ?
C3 H3 0.9500 . ?
C3 C37 1.383(5) . ?
C35 C33 1.405(5) . ?
C35 C36 1.485(5) . ?
C37 H37 0.9500 . ?
C37 C1 1.387(5) . ?
N3B C36 1.442(12) . ?
N3B C37B 1.351(14) . ?
N3B O2B 1.284(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C26 C25 1.396(5) . ?
C26 C27 1.508(5) . ?
C26 C21 1.382(5) . ?
C25 H25 0.9500 . ?
C25 C24 1.385(5) . ?
C13 C14 1.507(5) . ?
C33 C32 1.381(6) . ?
C33 C34 1.506(5) . ?
C1 H1 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C36 C40 1.367(5) . ?
C36 N3A 1.339(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.398(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.379(6) . ?
C40 H40 0.9500 . ?
C40 C39 1.389(5) . ?
C18 H18 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C39 H39 0.9500 . ?
C39 C38 1.356(5) . ?
C31 H31 0.9500 . ?
C38 C37B 1.493(17) . ?
C38 C37A 1.277(11) . ?
C23 H23 0.9500 . ?
C23 C22 1.385(6) . ?
C23 C24 1.378(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.381(6) . ?
C21 H21 0.9500 . ?
C24 H24 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C37B H37B 0.9500 . ?
O2B O2 1.748(10) . ?
O2A N3A 1.291(11) . ?
C37A H37A 0.9500 . ?
C37A N3A 1.364(12) . ?
O2 H2A 0.8700 . ?
O2 H2B 0.8699 . ?

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
O1 N1 C16 120.0(2) . . ?
O1 N1 C20 119.1(2) . . ?
C20 N1 C16 120.9(3) . . ?
H4A N4 H4B 107.7 . . ?
C28 N4 H4A 108.8 . . ?
C28 N4 H4B 108.8 . . ?
C28 N4 C27 113.9(2) . . ?
C27 N4 H4A 108.8 . . ?
C27 N4 H4B 108.8 . . ?
H2C N2 H2D 107.5 . . ?
C7 N2 H2C 108.5 . . ?
C7 N2 H2D 108.5 . . ?
C8 N2 H2C 108.5 . . ?
C8 N2 H2D 108.5 . . ?
C8 N2 C7 114.9(2) . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
N1 C16 C17 119.0(3) . . ?
N1 C16 C15 117.2(3) . . ?
C17 C16 C15 123.7(3) . . ?
N1 C20 H20 120.4 . . ?
N1 C20 C19 119.1(3) . . ?
C19 C20 H20 120.4 . . ?
C10 C9 C15 119.5(3) . . ?
C10 C9 C8 119.6(3) . . ?
C15 C9 C8 120.9(3) . . ?
N4 C28 H28A 109.1 . . ?
N4 C28 H28B 109.1 . . ?
N4 C28 C29 112.6(2) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
N2 C7 C6 112.3(3) . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 C1 118.8(3) . . ?
C1 C6 C7 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
F1 C19 C20 117.1(3) . . ?
F1 C19 C18 119.9(3) . . ?
C20 C19 C18 123.1(3) . . ?
C9 C15 C16 121.0(3) . . ?
C9 C15 C13 121.0(3) . . ?
C13 C15 C16 117.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.5(3) . . ?
C13 C12 H12 119.3 . . ?
C35 C29 C28 120.0(3) . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 C35 119.4(3) . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C37 120.2(3) . . ?
C37 C3 H3 119.9 . . ?
C29 C35 C33 121.0(3) . . ?
C29 C35 C36 121.0(3) . . ?
C33 C35 C36 118.0(3) . . ?
C3 C37 H37 120.1 . . ?
C3 C37 C1 119.7(3) . . ?
C1 C37 H37 120.1 . . ?
C37B N3B C36 116.2(8) . . ?
O2B N3B C36 123.8(7) . . ?
O2B N3B C37B 119.8(8) . . ?
N2 C8 C9 110.1(2) . . ?
N2 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C25 C26 C27 120.6(3) . . ?
C21 C26 C25 118.5(3) . . ?
C21 C26 C27 120.9(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C15 C13 C14 121.7(3) . . ?
C12 C13 C15 117.8(3) . . ?
C12 C13 C14 120.5(3) . . ?
C35 C33 C34 121.0(3) . . ?
C32 C33 C35 117.9(3) . . ?
C32 C33 C34 121.1(3) . . ?
C6 C1 H1 119.6 . . ?
C37 C1 C6 120.8(3) . . ?
C37 C1 H1 119.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3B C36 C35 112.1(6) . . ?
C40 C36 C35 124.0(3) . . ?
C40 C36 N3B 121.6(5) . . ?
N3A C36 C35 121.3(6) . . ?
N3A C36 C40 114.1(7) . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C33 C32 H32 119.0 . . ?
C31 C32 C33 122.0(3) . . ?
C31 C32 H32 119.0 . . ?
C36 C40 H40 118.7 . . ?
C36 C40 C39 122.6(3) . . ?
C39 C40 H40 118.7 . . ?
C17 C18 H18 121.8 . . ?
C19 C18 C17 116.4(3) . . ?
C19 C18 H18 121.8 . . ?
N4 C27 H27A 109.1 . . ?
N4 C27 H27B 109.1 . . ?
C26 C27 N4 112.4(3) . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
C40 C39 H39 122.2 . . ?
C38 C39 C40 115.6(3) . . ?
C38 C39 H39 122.2 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
F2 C38 C39 119.1(3) . . ?
F2 C38 C37B 117.5(5) . . ?
C39 C38 C37B 122.2(6) . . ?
C37A C38 F2 117.1(5) . . ?
C37A C38 C39 121.9(6) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C24 C23 C22 119.6(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C26 C21 H21 119.4 . . ?
C22 C21 C26 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N3B C37B C38 119.1(8) . . ?
N3B C37B H37B 120.5 . . ?
C38 C37B H37B 120.5 . . ?
N3B O2B O2 104.5(12) . . ?
C38 C37A H37A 120.5 . . ?
C38 C37A N3A 119.0(8) . . ?
N3A C37A H37A 120.5 . . ?
C36 N3A C37A 123.0(7) . . ?
O2A N3A C36 116.6(8) . . ?
O2A N3A C37A 120.3(7) . . ?
H2A O2 H2B 104.5 . . ?

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
F1 C19 C18 C17 177.3(3) . . . . ?
O1 N1 C16 C17 177.7(3) . . . . ?
O1 N1 C16 C15 -6.0(4) . . . . ?
O1 N1 C20 C19 -179.0(3) . . . . ?
N1 C16 C17 C18 1.6(5) . . . . ?
N1 C16 C15 C9 75.0(4) . . . . ?
N1 C16 C15 C13 -103.4(3) . . . . ?
N1 C20 C19 F1 -178.5(3) . . . . ?
N1 C20 C19 C18 1.1(5) . . . . ?
F2 C38 C37B N3B 178.4(7) . . . . ?
F2 C38 C37A N3A -179.8(8) . . . . ?
N4 C28 C29 C35 106.4(3) . . . . ?
N4 C28 C29 C30 -75.9(4) . . . . ?
N2 C7 C6 C5 -90.3(4) . . . . ?
N2 C7 C6 C1 89.8(4) . . . . ?
C5 C6 C1 C37 1.0(5) . . . . ?
C5 C4 C3 C37 0.7(5) . . . . ?
C16 N1 C20 C19 1.6(4) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C16 C15 C13 C12 175.5(3) . . . . ?
C16 C15 C13 C14 -3.3(4) . . . . ?
C20 N1 C16 C17 -2.9(4) . . . . ?
C20 N1 C16 C15 173.3(3) . . . . ?
C20 C19 C18 C17 -2.4(5) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C9 C15 C13 C12 -3.0(4) . . . . ?
C9 C15 C13 C14 178.2(3) . . . . ?
C28 N4 C27 C26 66.3(3) . . . . ?
C28 C29 C35 C33 176.6(3) . . . . ?
C28 C29 C35 C36 -3.5(5) . . . . ?
C28 C29 C30 C31 -177.4(3) . . . . ?
C10 C9 C15 C16 -175.7(3) . . . . ?
C10 C9 C15 C13 2.7(4) . . . . ?
C10 C9 C8 N2 85.8(3) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C7 N2 C8 C9 170.2(2) . . . . ?
C7 C6 C1 C37 -179.0(3) . . . . ?
C6 C5 C4 C3 -1.2(5) . . . . ?
C17 C16 C15 C9 -108.9(4) . . . . ?
C17 C16 C15 C13 72.7(4) . . . . ?
C15 C16 C17 C18 -174.4(3) . . . . ?
C15 C9 C10 C11 -0.4(4) . . . . ?
C15 C9 C8 N2 -93.2(3) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C4 C3 C37 C1 0.6(5) . . . . ?
C11 C12 C13 C15 1.0(5) . . . . ?
C11 C12 C13 C14 179.8(3) . . . . ?
C29 C35 C33 C32 0.8(5) . . . . ?
C29 C35 C33 C34 -178.4(3) . . . . ?
C29 C35 C36 N3B 97.0(11) . . . . ?
C29 C35 C36 C40 -100.2(4) . . . . ?
C29 C35 C36 N3A 70.2(14) . . . . ?
C29 C30 C31 C32 0.8(5) . . . . ?
C3 C37 C1 C6 -1.5(5) . . . . ?
C35 C29 C30 C31 0.2(5) . . . . ?
C35 C33 C32 C31 0.3(6) . . . . ?
C35 C36 C40 C39 -175.7(3) . . . . ?
C35 C36 N3A O2A -2(3) . . . . ?
C35 C36 N3A C37A 173.8(8) . . . . ?
N3B C36 C40 C39 -14.4(13) . . . . ?
C8 N2 C7 C6 -75.6(3) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C8 C9 C15 C16 3.3(4) . . . . ?
C8 C9 C15 C13 -178.3(3) . . . . ?
C26 C25 C24 C23 0.2(6) . . . . ?
C25 C26 C27 N4 84.8(4) . . . . ?
C25 C26 C21 C22 -1.7(6) . . . . ?
C33 C35 C36 N3B -83.1(11) . . . . ?
C33 C35 C36 C40 79.7(4) . . . . ?
C33 C35 C36 N3A -110.0(14) . . . . ?
C33 C32 C31 C30 -1.1(6) . . . . ?
C36 C35 C33 C32 -179.1(3) . . . . ?
C36 C35 C33 C34 1.8(5) . . . . ?
C36 N3B C37B C38 2.1(12) . . . . ?
C36 N3B O2B O2 116.7(19) . . . . ?
C36 C40 C39 C38 1.7(6) . . . . ?
C30 C29 C35 C33 -1.0(5) . . . . ?
C30 C29 C35 C36 178.8(3) . . . . ?
C40 C36 N3A O2A 168.8(15) . . . . ?
C40 C36 N3A C37A -15.0(15) . . . . ?
C40 C39 C38 F2 179.2(3) . . . . ?
C40 C39 C38 C37B 12.6(12) . . . . ?
C40 C39 C38 C37A -17.2(17) . . . . ?
C27 N4 C28 C29 -164.6(3) . . . . ?
C27 C26 C25 C24 178.3(3) . . . . ?
C27 C26 C21 C22 -179.2(3) . . . . ?
C39 C38 C37B N3B -14.9(16) . . . . ?
C39 C38 C37A N3A 16(2) . . . . ?
C38 C37A N3A C36 0.9(15) . . . . ?
C38 C37A N3A O2A 177(3) . . . . ?
C23 C22 C21 C26 1.7(6) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C21 C26 C25 C24 0.8(5) . . . . ?
C21 C26 C27 N4 -97.7(4) . . . . ?
C24 C23 C22 C21 -0.7(6) . . . . ?
C34 C33 C32 C31 179.4(4) . . . . ?
C37B N3B C36 C35 175.0(7) . . . . ?
C37B N3B C36 C40 11.7(14) . . . . ?
C37B N3B O2B O2 -68.0(12) . . . . ?
O2B N3B C36 C35 -10(2) . . . . ?
O2B N3B C36 C40 -172.9(15) . . . . ?
O2B N3B C37B C38 -173(2) . . . . ?
N3A C36 C40 C39 13.3(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.964
_oxdiff_exptl_absorpt_empirical_full_min 0.488
