# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_huyuehong_0707_auto
_database_code_depnum_ccdc_archive 'CCDC 2408876'
loop_
_audit_author_name
_audit_author_address
'Yuehong hu'
;Lanzhou University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_chemical_melting_point          ?
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.38050(10)
_cell_length_b                   17.9125(3)
_cell_length_c                   20.6371(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3467.61(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      75.8270
_cell_measurement_theta_min      5.3640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.081
_diffrn_reflns_theta_min         4.285
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(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 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  22.00   0.50    0.80    --   46.32 -19.00 120.00  100
  2  ω     32.00  57.00   0.50    1.10    --  104.25 -61.00 120.00   50
  3  ω     48.00  73.00   0.50    1.10    --  104.25-127.00  57.00   50
  4  ω    -20.00  30.00   0.50    0.80    --   46.32  -7.00-120.00  100
  5  ω     76.00 113.00   0.50    1.10    --  104.25-127.00  57.00   74
  6  ω     36.00 111.00   0.50    1.10    --  104.25-125.00 147.00  150
  7  ω   -165.00-127.00   0.50    1.10    -- -102.00 -61.00-120.00   76
  8  ω   -174.00 -97.00   0.50    1.10    -- -102.00  -7.00-120.00  154
  9  ω    -85.00 -56.00   0.50    0.80    --  -46.32 125.00-134.00   58
 10  ω    -79.00 -34.00   0.50    1.10    -- -102.00 125.00 -30.00   90
 11  ω   -112.00 -86.00   0.50    1.10    -- -102.00 125.00  90.00   52
 12  ω    -78.00 -39.00   0.50    1.10    -- -102.00 125.00  90.00   78
 13  ω     -7.00  27.00   0.50    0.80    --  -46.32  19.00 -30.00   68
 14  ω    -69.00 -39.00   0.50    1.10    -- -102.00  61.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0128597000
_diffrn_orient_matrix_UB_12      -0.0852580000
_diffrn_orient_matrix_UB_13      0.0077405000
_diffrn_orient_matrix_UB_21      0.0083783000
_diffrn_orient_matrix_UB_22      -0.0093032000
_diffrn_orient_matrix_UB_23      -0.0741099000
_diffrn_orient_matrix_UB_31      0.1635504000
_diffrn_orient_matrix_UB_32      -0.0061992000
_diffrn_orient_matrix_UB_33      0.0044672000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2991
_reflns_number_total             3472
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.032
_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)+(0.0521P)²+1.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C004(H004)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00J(H00L), C00K(H00M), C00M(H00Q), C00N(H00R), C00O(H00S)
2.c Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00H), C00I(H00I,H00J,H00K), C00L(H00N,H00O,H00P)
;
_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 0.36441(9) 0.66627(6) 0.77133(5) 0.0337(2) Uani 1 1 d . . . . .
O002 O 0.16270(11) 0.47974(6) 0.53360(4) 0.0350(2) Uani 1 1 d . . . . .
N003 N 0.15711(10) 0.62507(6) 0.72822(5) 0.0212(2) Uani 1 1 d . . . . .
H003 H 0.063684 0.629498 0.728220 0.025 Uiso 1 1 calc R U . . .
C004 C 0.22194(12) 0.56853(7) 0.68753(6) 0.0208(2) Uani 1 1 d . . . . .
H004 H 0.327134 0.570231 0.695240 0.025 Uiso 1 1 calc R U . . .
C005 C 0.23431(13) 0.67105(7) 0.76598(6) 0.0232(3) Uani 1 1 d . . . . .
C006 C 0.16445(13) 0.46042(7) 0.76822(6) 0.0236(3) Uani 1 1 d . . . . .
C007 C 0.32789(13) 0.61297(7) 0.58087(6) 0.0247(3) Uani 1 1 d . . . . .
C008 C 0.19684(13) 0.57929(7) 0.61309(6) 0.0233(3) Uani 1 1 d . . . . .
C009 C 0.17229(12) 0.48926(7) 0.70142(6) 0.0224(3) Uani 1 1 d . . . . .
C00A C 0.17025(12) 0.49909(7) 0.59004(6) 0.0253(3) Uani 1 1 d . . . . .
C00B C 0.15093(13) 0.45000(7) 0.64657(6) 0.0253(3) Uani 1 1 d . . . . .
C00C C 0.26359(14) 0.48324(7) 0.81450(6) 0.0273(3) Uani 1 1 d . . . . .
H00C H 0.333202 0.519571 0.803398 0.033 Uiso 1 1 calc R U . . .
C00D C 0.33304(16) 0.68638(7) 0.55972(6) 0.0315(3) Uani 1 1 d . . . . .
H00D H 0.251356 0.717285 0.564298 0.038 Uiso 1 1 calc R U . . .
C00E C 0.05994(14) 0.40855(7) 0.78630(6) 0.0290(3) Uani 1 1 d . . . . .
H00E H -0.009761 0.393100 0.755715 0.035 Uiso 1 1 calc R U . . .
C00F C 0.44981(15) 0.56945(8) 0.57354(7) 0.0338(3) Uani 1 1 d . . . . .
H00F H 0.448917 0.519171 0.588176 0.041 Uiso 1 1 calc R U . . .
C00G C 0.26177(15) 0.45348(8) 0.87665(7) 0.0328(3) Uani 1 1 d . . . . .
H00G H 0.330974 0.468728 0.907545 0.039 Uiso 1 1 calc R U . . .
C00H C 0.05826(14) 0.62179(8) 0.59816(6) 0.0315(3) Uani 1 1 d . . . . .
H00A H 0.065471 0.672867 0.614843 0.047 Uiso 1 1 calc R U . . .
H00B H -0.022184 0.596364 0.618924 0.047 Uiso 1 1 calc R U . . .
H00H H 0.043153 0.623205 0.551184 0.047 Uiso 1 1 calc R U . . .
C00I C 0.15143(15) 0.72957(8) 0.80219(7) 0.0333(3) Uani 1 1 d . . . . .
H00I H 0.194814 0.778618 0.794843 0.050 Uiso 1 1 calc R U . . .
H00J H 0.152787 0.718131 0.848622 0.050 Uiso 1 1 calc R U . . .
H00K H 0.052680 0.730105 0.786695 0.050 Uiso 1 1 calc R U . . .
C00J C 0.15882(16) 0.40151(8) 0.89352(7) 0.0363(3) Uani 1 1 d . . . . .
H00L H 0.157720 0.380895 0.935928 0.044 Uiso 1 1 calc R U . . .
C00K C 0.05782(16) 0.37967(8) 0.84866(7) 0.0361(3) Uani 1 1 d . . . . .
H00M H -0.013558 0.344652 0.860595 0.043 Uiso 1 1 calc R U . . .
C00L C 0.12242(17) 0.36864(8) 0.63695(7) 0.0353(3) Uani 1 1 d . . . . .
H00N H 0.020215 0.360880 0.629763 0.053 Uiso 1 1 calc R U . . .
H00O H 0.152531 0.340974 0.675564 0.053 Uiso 1 1 calc R U . . .
H00P H 0.175815 0.350725 0.599211 0.053 Uiso 1 1 calc R U . . .
C00M C 0.45634(18) 0.71541(8) 0.53187(7) 0.0389(4) Uani 1 1 d . . . . .
H00Q H 0.458463 0.765921 0.517865 0.047 Uiso 1 1 calc R U . . .
C00N C 0.57512(17) 0.67114(9) 0.52457(7) 0.0389(4) Uani 1 1 d . . . . .
H00R H 0.658929 0.690898 0.505240 0.047 Uiso 1 1 calc R U . . .
C00O C 0.57216(16) 0.59782(9) 0.54544(7) 0.0385(3) Uani 1 1 d . . . . .
H00S H 0.653908 0.567040 0.540498 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.2283(15) . ?
O002 C00A 1.2173(15) . ?
N003 H003 0.8800 . ?
N003 C004 1.4493(15) . ?
N003 C005 1.3454(16) . ?
C004 H004 1.0000 . ?
C004 C008 1.5661(16) . ?
C004 C009 1.5215(17) . ?
C005 C00I 1.5039(17) . ?
C006 C009 1.4741(16) . ?
C006 C00C 1.3943(18) . ?
C006 C00E 1.4012(18) . ?
C007 C008 1.5222(17) . ?
C007 C00D 1.3863(18) . ?
C007 C00F 1.3922(18) . ?
C008 C00A 1.5338(18) . ?
C008 C00H 1.5376(17) . ?
C009 C00B 1.3475(17) . ?
C00A C00B 1.4721(17) . ?
C00B C00L 1.4950(18) . ?
C00C H00C 0.9500 . ?
C00C C00G 1.3891(18) . ?
C00D H00D 0.9500 . ?
C00D C00M 1.392(2) . ?
C00E H00E 0.9500 . ?
C00E C00K 1.3873(18) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.3827(19) . ?
C00G H00G 0.9500 . ?
C00G C00J 1.386(2) . ?
C00H H00A 0.9800 . ?
C00H H00B 0.9800 . ?
C00H H00H 0.9800 . ?
C00I H00I 0.9800 . ?
C00I H00J 0.9800 . ?
C00I H00K 0.9800 . ?
C00J H00L 0.9500 . ?
C00J C00K 1.381(2) . ?
C00K H00M 0.9500 . ?
C00L H00N 0.9800 . ?
C00L H00O 0.9800 . ?
C00L H00P 0.9800 . ?
C00M H00Q 0.9500 . ?
C00M C00N 1.376(2) . ?
C00N H00R 0.9500 . ?
C00N C00O 1.382(2) . ?
C00O H00S 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
C004 N003 H003 118.7 . . ?
C005 N003 H003 118.7 . . ?
C005 N003 C004 122.52(10) . . ?
N003 C004 H004 107.5 . . ?
N003 C004 C008 114.78(9) . . ?
N003 C004 C009 114.50(10) . . ?
C008 C004 H004 107.5 . . ?
C009 C004 H004 107.5 . . ?
C009 C004 C008 104.70(10) . . ?
O001 C005 N003 122.97(11) . . ?
O001 C005 C00I 121.16(11) . . ?
N003 C005 C00I 115.86(11) . . ?
C00C C006 C009 120.30(11) . . ?
C00C C006 C00E 118.60(11) . . ?
C00E C006 C009 121.09(11) . . ?
C00D C007 C008 122.78(11) . . ?
C00D C007 C00F 117.92(12) . . ?
C00F C007 C008 119.27(11) . . ?
C007 C008 C004 110.85(10) . . ?
C007 C008 C00A 111.53(10) . . ?
C007 C008 C00H 113.52(10) . . ?
C00A C008 C004 102.32(10) . . ?
C00A C008 C00H 105.30(10) . . ?
C00H C008 C004 112.62(10) . . ?
C006 C009 C004 121.23(11) . . ?
C00B C009 C004 111.98(11) . . ?
C00B C009 C006 126.53(12) . . ?
O002 C00A C008 124.96(12) . . ?
O002 C00A C00B 125.53(12) . . ?
C00B C00A C008 109.49(10) . . ?
C009 C00B C00A 109.61(11) . . ?
C009 C00B C00L 130.31(12) . . ?
C00A C00B C00L 119.93(11) . . ?
C006 C00C H00C 119.6 . . ?
C00G C00C C006 120.78(13) . . ?
C00G C00C H00C 119.6 . . ?
C007 C00D H00D 119.6 . . ?
C007 C00D C00M 120.87(13) . . ?
C00M C00D H00D 119.6 . . ?
C006 C00E H00E 119.9 . . ?
C00K C00E C006 120.28(13) . . ?
C00K C00E H00E 119.9 . . ?
C007 C00F H00F 119.3 . . ?
C00O C00F C007 121.44(13) . . ?
C00O C00F H00F 119.3 . . ?
C00C C00G H00G 120.1 . . ?
C00J C00G C00C 119.88(13) . . ?
C00J C00G H00G 120.1 . . ?
C008 C00H H00A 109.5 . . ?
C008 C00H H00B 109.5 . . ?
C008 C00H H00H 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00H 109.5 . . ?
H00B C00H H00H 109.5 . . ?
C005 C00I H00I 109.5 . . ?
C005 C00I H00J 109.5 . . ?
C005 C00I H00K 109.5 . . ?
H00I C00I H00J 109.5 . . ?
H00I C00I H00K 109.5 . . ?
H00J C00I H00K 109.5 . . ?
C00G C00J H00L 120.0 . . ?
C00K C00J C00G 120.00(13) . . ?
C00K C00J H00L 120.0 . . ?
C00E C00K H00M 119.8 . . ?
C00J C00K C00E 120.42(13) . . ?
C00J C00K H00M 119.8 . . ?
C00B C00L H00N 109.5 . . ?
C00B C00L H00O 109.5 . . ?
C00B C00L H00P 109.5 . . ?
H00N C00L H00O 109.5 . . ?
H00N C00L H00P 109.5 . . ?
H00O C00L H00P 109.5 . . ?
C00D C00M H00Q 119.9 . . ?
C00N C00M C00D 120.17(13) . . ?
C00N C00M H00Q 119.9 . . ?
C00M C00N H00R 120.1 . . ?
C00M C00N C00O 119.82(13) . . ?
C00O C00N H00R 120.1 . . ?
C00F C00O H00S 120.1 . . ?
C00N C00O C00F 119.77(14) . . ?
C00N C00O H00S 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O002 C00A C00B C009 177.51(12) . . . . ?
O002 C00A C00B C00L 1.4(2) . . . . ?
N003 C004 C008 C007 101.27(11) . . . . ?
N003 C004 C008 C00A -139.71(10) . . . . ?
N003 C004 C008 C00H -27.15(15) . . . . ?
N003 C004 C009 C006 -46.79(14) . . . . ?
N003 C004 C009 C00B 138.67(11) . . . . ?
C004 N003 C005 O001 -3.70(18) . . . . ?
C004 N003 C005 C00I 176.50(11) . . . . ?
C004 C008 C00A O002 -170.63(12) . . . . ?
C004 C008 C00A C00B 11.13(12) . . . . ?
C004 C009 C00B C00A -5.14(14) . . . . ?
C004 C009 C00B C00L 170.45(13) . . . . ?
C005 N003 C004 C008 -117.07(12) . . . . ?
C005 N003 C004 C009 121.77(12) . . . . ?
C006 C009 C00B C00A -179.33(11) . . . . ?
C006 C009 C00B C00L -3.7(2) . . . . ?
C006 C00C C00G C00J -1.2(2) . . . . ?
C006 C00E C00K C00J -0.2(2) . . . . ?
C007 C008 C00A O002 -52.08(16) . . . . ?
C007 C008 C00A C00B 129.68(11) . . . . ?
C007 C00D C00M C00N 0.4(2) . . . . ?
C007 C00F C00O C00N 0.6(2) . . . . ?
C008 C004 C009 C006 -173.35(10) . . . . ?
C008 C004 C009 C00B 12.11(13) . . . . ?
C008 C007 C00D C00M 178.46(12) . . . . ?
C008 C007 C00F C00O -179.05(13) . . . . ?
C008 C00A C00B C009 -4.26(14) . . . . ?
C008 C00A C00B C00L 179.62(12) . . . . ?
C009 C004 C008 C007 -132.35(10) . . . . ?
C009 C004 C008 C00A -13.32(11) . . . . ?
C009 C004 C008 C00H 99.24(12) . . . . ?
C009 C006 C00C C00G -176.61(12) . . . . ?
C009 C006 C00E C00K 177.31(12) . . . . ?
C00C C006 C009 C004 -34.24(17) . . . . ?
C00C C006 C009 C00B 139.46(13) . . . . ?
C00C C006 C00E C00K -1.31(19) . . . . ?
C00C C00G C00J C00K -0.3(2) . . . . ?
C00D C007 C008 C004 -106.84(13) . . . . ?
C00D C007 C008 C00A 139.85(12) . . . . ?
C00D C007 C008 C00H 21.09(17) . . . . ?
C00D C007 C00F C00O -0.7(2) . . . . ?
C00D C00M C00N C00O -0.5(2) . . . . ?
C00E C006 C009 C004 147.17(12) . . . . ?
C00E C006 C009 C00B -39.13(18) . . . . ?
C00E C006 C00C C00G 2.02(19) . . . . ?
C00F C007 C008 C004 71.40(15) . . . . ?
C00F C007 C008 C00A -41.91(15) . . . . ?
C00F C007 C008 C00H -160.67(12) . . . . ?
C00F C007 C00D C00M 0.2(2) . . . . ?
C00G C00J C00K C00E 1.0(2) . . . . ?
C00H C008 C00A O002 71.47(15) . . . . ?
C00H C008 C00A C00B -106.77(11) . . . . ?
C00M C00N C00O C00F 0.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.764
####################################################################### 
# 
# 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_huyuehong_0831_auto
_database_code_depnum_ccdc_archive 'CCDC 2408878'
loop_
_audit_author_name
_audit_author_address
'Yuehong hu'
;Lanzhou University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_audit_creation_date             2022-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H16 Cl N O2)'
_chemical_formula_sum            'C36 H32 Cl2 N2 O4'
_chemical_formula_weight         627.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.74490(10)
_cell_length_b                   12.6197(3)
_cell_length_c                   12.8104(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.761(2)
_cell_angle_gamma                90
_cell_volume                     1574.65(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7835
_cell_measurement_temperature    301.46(10)
_cell_measurement_theta_max      77.0390
_cell_measurement_theta_min      3.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11508
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.922
_diffrn_reflns_theta_min         3.452
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.46(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     74.00 102.00   0.50    0.15    --   47.57 133.00 116.00   56
  2  ω     72.00 120.00   0.50    0.15    --   47.57 135.00 -64.00   96
  3  ω    141.00 166.00   0.50    0.61    --  107.75 135.00 -64.00   50
  4  ω     95.00 131.00   0.50    0.61    --  107.75  19.00 120.00   72
  5  ω    146.00 175.00   0.50    0.61    --  107.75  19.00 120.00   58
  6  ω     58.00 108.00   0.50    0.61    --  107.75-109.00  72.38  100
  7  ω     33.00  60.00   0.50    0.15    --   47.57-133.00  48.00   54
  8  ω     35.00 118.00   0.50    0.61    --  107.75-133.00  48.00  166
  9  ω     35.00  63.00   0.50    0.61    --  107.75-135.00-129.00   56
 10  ω     49.00  80.00   0.50    0.61    --  107.75 -77.00-150.00   62
 11  ω     36.00  62.00   0.50    0.61    --  107.75 -57.00-180.00   52
 12  ω     -3.00  23.00   0.50    0.15    --   47.57 -19.00 -90.00   52
 13  ω    -27.00  23.00   0.50    0.15    --   47.57 -19.00  30.00  100
 14  ω     36.00  61.00   0.50    0.61    --  107.75 -57.00  90.00   50
 15  ω     36.00  63.00   0.50    0.61    --  107.75 -57.00  30.00   54
 16  ω    -26.00  28.00   0.50    0.15    --  -47.57  19.00  30.00  108
 17  ω    -98.00 -51.00   0.50    0.15    --  -47.57 133.00 116.00   94
 18  ω   -115.00 -71.00   0.50    0.61    -- -100.00 133.00 116.00   88
 19  ω   -111.00 -28.00   0.50    0.61    -- -100.00 125.00 -90.00  166
 20  ω    -56.00 -28.00   0.50    0.61    -- -100.00  57.00-150.00   56
 21  ω   -172.00-147.00   0.50    0.61    -- -100.00 -37.00 -60.00   50
 22  ω   -161.00-136.00   0.50    0.61    -- -100.00 -99.00  90.00   50
 23  ω   -119.00 -91.00   0.50    0.61    -- -100.00 -99.00  90.00   56
 24  ω   -149.00-124.00   0.50    0.61    -- -100.00-133.00  48.00   50
 25  ω   -173.00 -91.00   0.50    0.61    -- -100.00 -99.00 -30.00  164
 26  ω   -127.00 -87.00   0.50    0.61    -- -100.00 -37.00 -60.00   80
 27  ω   -103.00 -77.00   0.50    0.61    -- -100.00-135.00-129.00   52
 28  ω     69.00  94.00   0.50    0.15    --   47.57  77.00 -90.00   50
 29  ω     35.00  60.00   0.50    0.61    --  107.75 -57.00 -60.00   50
 30  ω     35.00  60.00   0.50    0.61    --  107.75 -57.00 120.00   50
 31  ω     35.00  60.00   0.50    0.61    --  107.75 -57.00-120.00   50
;
_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      0.0338799000
_diffrn_orient_matrix_UB_12      -0.0337317000
_diffrn_orient_matrix_UB_13      -0.1119216000
_diffrn_orient_matrix_UB_21      -0.0044810000
_diffrn_orient_matrix_UB_22      -0.1172606000
_diffrn_orient_matrix_UB_23      0.0331240000
_diffrn_orient_matrix_UB_31      -0.1543929000
_diffrn_orient_matrix_UB_32      -0.0040112000
_diffrn_orient_matrix_UB_33      -0.0292665000
_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         0.666
_reflns_Friedel_fraction_full    0.758
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                4909
_reflns_number_total             5451
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1729 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.268(10)
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.097
_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)+(0.0625P)²+0.2953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C15(H15), C28(H28), C29(H29), C30(H30), C32(H32),
 C9(H9), C13(H13), C25(H25), C26(H26), C31(H31), C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C)
;
_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 0.81392(11) 0.68376(13) 0.28883(14) 0.0920(5) Uani 1 1 d . . . . .
O1 O 0.4249(2) 0.4659(3) 0.5815(2) 0.0626(8) Uani 1 1 d . . . . .
O4 O 0.1280(3) 0.6082(3) 0.1971(3) 0.0629(8) Uani 1 1 d . . . . .
N1 N 0.2030(3) 0.4535(3) 0.5347(2) 0.0438(7) Uani 1 1 d . . . . .
H1 H 0.122(4) 0.453(3) 0.551(3) 0.029(8) Uiso 1 1 d . . . . .
C1 C 0.0752(3) 0.4406(3) 0.2736(3) 0.0410(7) Uani 1 1 d . . . . .
C2 C 0.5750(4) 0.5845(5) 0.2439(4) 0.0667(13) Uani 1 1 d . . . . .
H2 H 0.619278 0.555422 0.187328 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1458(4) 0.6455(3) 0.4312(4) 0.0534(9) Uani 1 1 d . . . . .
H3A H 0.134780 0.709013 0.390533 0.080 Uiso 1 1 calc R U . . .
H3B H 0.194600 0.661501 0.495450 0.080 Uiso 1 1 calc R U . . .
H3C H 0.057090 0.617107 0.446069 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1407(3) 0.5447(3) 0.2684(3) 0.0444(8) Uani 1 1 d . . . . .
C5 C -0.0138(4) 0.2393(4) 0.3132(4) 0.0551(10) Uani 1 1 d . . . . .
H5 H -0.043813 0.170538 0.325486 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2286(3) 0.4523(3) 0.4238(3) 0.0384(7) Uani 1 1 d . . . . .
H6 H 0.319018 0.420357 0.414114 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2269(3) 0.5638(3) 0.3696(3) 0.0412(7) Uani 1 1 d . . . . .
C11 C -0.0625(4) 0.2925(4) 0.2248(4) 0.0588(11) Uani 1 1 d . . . . .
H11 H -0.125032 0.259458 0.179206 0.071 Uiso 1 1 calc R U . . .
C12 C 0.3041(3) 0.4641(3) 0.6063(3) 0.0446(8) Uani 1 1 d . . . . .
C15 C 0.5790(4) 0.6973(4) 0.3931(4) 0.0626(11) Uani 1 1 d . . . . .
H15 H 0.625917 0.744162 0.437383 0.075 Uiso 1 1 calc R U . . .
C17 C 0.2624(4) 0.4745(5) 0.7169(3) 0.0614(11) Uani 1 1 d . . . . .
H17A H 0.306167 0.420057 0.758356 0.092 Uiso 1 1 calc R U . . .
H17B H 0.164541 0.467293 0.720196 0.092 Uiso 1 1 calc R U . . .
H17C H 0.289613 0.542729 0.743357 0.092 Uiso 1 1 calc R U . . .
C18 C 0.1240(3) 0.3881(3) 0.3627(3) 0.0392(7) Uani 1 1 d . . . . .
C20 C 0.3714(3) 0.6010(3) 0.3469(3) 0.0421(7) Uani 1 1 d . . . . .
C21 C 0.6418(4) 0.6533(4) 0.3095(4) 0.0572(10) Uani 1 1 d . . . . .
C28 C -0.0186(4) 0.3948(4) 0.2038(3) 0.0532(9) Uani 1 1 d . . . . .
H28 H -0.050987 0.431270 0.145014 0.064 Uiso 1 1 calc R U . . .
C29 C 0.4399(4) 0.5586(4) 0.2628(3) 0.0576(11) Uani 1 1 d . . . . .
H29 H 0.393732 0.511570 0.218215 0.069 Uiso 1 1 calc R U . . .
C30 C 0.4435(4) 0.6702(3) 0.4102(3) 0.0512(9) Uani 1 1 d . . . . .
H30 H 0.400041 0.700190 0.466668 0.061 Uiso 1 1 calc R U . . .
C32 C 0.0782(4) 0.2859(3) 0.3836(3) 0.0475(8) Uani 1 1 d . . . . .
H32 H 0.108772 0.249985 0.443247 0.057 Uiso 1 1 calc R U . . .
Cl2 Cl 1.31976(13) 0.40805(18) 1.01426(12) 0.1004(6) Uani 1 1 d . . . . .
O2 O 0.9248(3) 0.4879(3) 0.6041(3) 0.0666(9) Uani 1 1 d . . . . .
O3 O 0.6554(4) 0.4839(3) 1.0167(2) 0.0734(10) Uani 1 1 d . . . . .
N2 N 0.7039(3) 0.5010(3) 0.6455(2) 0.0483(8) Uani 1 1 d . . . . .
H2A H 0.611(6) 0.487(5) 0.625(4) 0.081(17) Uiso 1 1 d . . . . .
C7 C 1.1530(4) 0.4227(4) 0.9649(3) 0.0610(12) Uani 1 1 d . . . . .
C9 C 0.9636(4) 0.5322(3) 0.9170(3) 0.0476(8) Uani 1 1 d . . . . .
H9 H 0.924750 0.599464 0.912365 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8029(3) 0.4762(3) 0.5803(3) 0.0451(8) Uani 1 1 d . . . . .
C13 C 0.5604(4) 0.7013(4) 0.7195(4) 0.0634(11) Uani 1 1 d . . . . .
H13 H 0.584973 0.711994 0.650684 0.076 Uiso 1 1 calc R U . . .
C14 C 0.7319(3) 0.5445(3) 0.7489(3) 0.0409(7) Uani 1 1 d . . . . .
H14 H 0.818940 0.583303 0.747885 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7404(3) 0.4624(3) 0.8412(3) 0.0424(7) Uani 1 1 d . . . . .
C19 C 0.6578(4) 0.5150(4) 0.9268(3) 0.0489(9) Uani 1 1 d . . . . .
C22 C 0.5822(4) 0.6056(3) 0.8811(3) 0.0497(9) Uani 1 1 d . . . . .
C23 C 0.6645(5) 0.3598(4) 0.8129(4) 0.0620(11) Uani 1 1 d . . . . .
H23A H 0.572514 0.376182 0.789167 0.093 Uiso 1 1 calc R U . . .
H23B H 0.661792 0.314938 0.873277 0.093 Uiso 1 1 calc R U . . .
H23C H 0.711544 0.323986 0.758401 0.093 Uiso 1 1 calc R U . . .
C24 C 0.6203(3) 0.6208(3) 0.7797(3) 0.0462(8) Uani 1 1 d . . . . .
C25 C 1.0804(5) 0.3351(5) 0.9325(4) 0.0670(13) Uani 1 1 d . . . . .
H25 H 1.119905 0.268214 0.938263 0.080 Uiso 1 1 calc R U . . .
C26 C 1.0961(4) 0.5216(4) 0.9574(3) 0.0577(10) Uani 1 1 d . . . . .
H26 H 1.145916 0.580914 0.979246 0.069 Uiso 1 1 calc R U . . .
C27 C 0.7554(4) 0.4342(4) 0.4758(3) 0.0541(9) Uani 1 1 d . . . . .
H27A H 0.794006 0.476265 0.421565 0.081 Uiso 1 1 calc R U . . .
H27B H 0.657016 0.437547 0.470051 0.081 Uiso 1 1 calc R U . . .
H27C H 0.784665 0.362005 0.468842 0.081 Uiso 1 1 calc R U . . .
C31 C 0.4850(4) 0.6705(4) 0.9279(4) 0.0664(13) Uani 1 1 d . . . . .
H31 H 0.460912 0.659847 0.996793 0.080 Uiso 1 1 calc R U . . .
C33 C 0.4266(5) 0.7501(5) 0.8689(5) 0.0784(17) Uani 1 1 d . . . . .
H33 H 0.362125 0.794624 0.898204 0.094 Uiso 1 1 calc R U . . .
C34 C 0.9470(5) 0.3462(4) 0.8909(3) 0.0560(10) Uani 1 1 d . . . . .
H34 H 0.898426 0.286559 0.868466 0.067 Uiso 1 1 calc R U . . .
C35 C 0.4628(5) 0.7651(5) 0.7653(6) 0.0789(16) Uani 1 1 d . . . . .
H35 H 0.420775 0.818783 0.726252 0.095 Uiso 1 1 calc R U . . .
C36 C 0.8866(4) 0.4452(3) 0.8829(3) 0.0432(7) 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
Cl1 C21 1.748(4) . ?
O1 C12 1.229(4) . ?
O4 C4 1.218(5) . ?
N1 H1 0.82(4) . ?
N1 C6 1.450(4) . ?
N1 C12 1.332(5) . ?
C1 C4 1.464(5) . ?
C1 C18 1.391(5) . ?
C1 C28 1.384(5) . ?
C2 H2 0.9300 . ?
C2 C21 1.360(7) . ?
C2 C29 1.386(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C8 1.532(5) . ?
C4 C8 1.542(5) . ?
C5 H5 0.9300 . ?
C5 C11 1.388(7) . ?
C5 C32 1.383(6) . ?
C6 H6 0.9800 . ?
C6 C8 1.569(5) . ?
C6 C18 1.503(5) . ?
C8 C20 1.521(5) . ?
C11 H11 0.9300 . ?
C11 C28 1.389(7) . ?
C12 C17 1.492(5) . ?
C15 H15 0.9300 . ?
C15 C21 1.368(7) . ?
C15 C30 1.387(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C32 1.393(5) . ?
C20 C29 1.392(5) . ?
C20 C30 1.371(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C32 H32 0.9300 . ?
Cl2 C7 1.736(4) . ?
O2 C10 1.226(5) . ?
O3 C19 1.218(5) . ?
N2 H2A 0.95(6) . ?
N2 C10 1.333(4) . ?
N2 C14 1.452(5) . ?
C7 C25 1.370(8) . ?
C7 C26 1.368(7) . ?
C9 H9 0.9300 . ?
C9 C26 1.384(6) . ?
C9 C36 1.392(6) . ?
C10 C27 1.499(5) . ?
C13 H13 0.9300 . ?
C13 C24 1.393(6) . ?
C13 C35 1.390(7) . ?
C14 H14 0.9800 . ?
C14 C16 1.572(5) . ?
C14 C24 1.514(5) . ?
C16 C19 1.531(5) . ?
C16 C23 1.529(6) . ?
C16 C36 1.522(5) . ?
C19 C22 1.472(6) . ?
C22 C24 1.375(6) . ?
C22 C31 1.401(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25 0.9300 . ?
C25 C34 1.396(7) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C31 H31 0.9300 . ?
C31 C33 1.371(9) . ?
C33 H33 0.9300 . ?
C33 C35 1.397(9) . ?
C34 H34 0.9300 . ?
C34 C36 1.384(6) . ?
C35 H35 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
C6 N1 H1 117(2) . . ?
C12 N1 H1 121(2) . . ?
C12 N1 C6 122.0(3) . . ?
C18 C1 C4 109.0(3) . . ?
C28 C1 C4 128.8(4) . . ?
C28 C1 C18 122.2(4) . . ?
C21 C2 H2 120.6 . . ?
C21 C2 C29 118.8(4) . . ?
C29 C2 H2 120.6 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C8 C3 H3A 109.5 . . ?
C8 C3 H3B 109.5 . . ?
C8 C3 H3C 109.5 . . ?
O4 C4 C1 126.2(3) . . ?
O4 C4 C8 124.6(3) . . ?
C1 C4 C8 109.2(3) . . ?
C11 C5 H5 119.2 . . ?
C32 C5 H5 119.2 . . ?
C32 C5 C11 121.6(4) . . ?
N1 C6 H6 108.1 . . ?
N1 C6 C8 115.1(3) . . ?
N1 C6 C18 112.4(3) . . ?
C8 C6 H6 108.1 . . ?
C18 C6 H6 108.1 . . ?
C18 C6 C8 104.8(3) . . ?
C3 C8 C4 105.2(3) . . ?
C3 C8 C6 112.0(3) . . ?
C4 C8 C6 103.3(3) . . ?
C20 C8 C3 112.7(3) . . ?
C20 C8 C4 111.8(3) . . ?
C20 C8 C6 111.3(3) . . ?
C5 C11 H11 119.7 . . ?
C5 C11 C28 120.5(4) . . ?
C28 C11 H11 119.7 . . ?
O1 C12 N1 121.2(3) . . ?
O1 C12 C17 122.3(3) . . ?
N1 C12 C17 116.5(3) . . ?
C21 C15 H15 120.8 . . ?
C21 C15 C30 118.3(4) . . ?
C30 C15 H15 120.8 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 C6 112.4(3) . . ?
C1 C18 C32 119.7(3) . . ?
C32 C18 C6 127.9(3) . . ?
C29 C20 C8 119.8(3) . . ?
C30 C20 C8 123.0(3) . . ?
C30 C20 C29 117.0(3) . . ?
C2 C21 Cl1 119.3(4) . . ?
C2 C21 C15 121.7(4) . . ?
C15 C21 Cl1 118.9(4) . . ?
C1 C28 C11 117.7(4) . . ?
C1 C28 H28 121.2 . . ?
C11 C28 H28 121.2 . . ?
C2 C29 C20 121.7(4) . . ?
C2 C29 H29 119.2 . . ?
C20 C29 H29 119.2 . . ?
C15 C30 H30 118.8 . . ?
C20 C30 C15 122.4(4) . . ?
C20 C30 H30 118.8 . . ?
C5 C32 C18 118.3(4) . . ?
C5 C32 H32 120.9 . . ?
C18 C32 H32 120.9 . . ?
C10 N2 H2A 119(3) . . ?
C10 N2 C14 122.8(3) . . ?
C14 N2 H2A 118(3) . . ?
C25 C7 Cl2 119.6(4) . . ?
C26 C7 Cl2 119.7(4) . . ?
C26 C7 C25 120.7(4) . . ?
C26 C9 H9 119.0 . . ?
C26 C9 C36 121.9(4) . . ?
C36 C9 H9 119.0 . . ?
O2 C10 N2 122.0(4) . . ?
O2 C10 C27 122.3(3) . . ?
N2 C10 C27 115.7(3) . . ?
C24 C13 H13 121.0 . . ?
C35 C13 H13 121.0 . . ?
C35 C13 C24 117.9(5) . . ?
N2 C14 H14 108.3 . . ?
N2 C14 C16 116.2(3) . . ?
N2 C14 C24 111.2(3) . . ?
C16 C14 H14 108.3 . . ?
C24 C14 H14 108.3 . . ?
C24 C14 C16 104.2(3) . . ?
C19 C16 C14 103.7(3) . . ?
C23 C16 C14 111.4(3) . . ?
C23 C16 C19 106.0(3) . . ?
C36 C16 C14 112.6(3) . . ?
C36 C16 C19 108.5(3) . . ?
C36 C16 C23 113.8(3) . . ?
O3 C19 C16 124.3(4) . . ?
O3 C19 C22 127.0(4) . . ?
C22 C19 C16 108.7(3) . . ?
C24 C22 C19 109.7(3) . . ?
C24 C22 C31 121.9(4) . . ?
C31 C22 C19 128.4(4) . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 C14 127.7(4) . . ?
C22 C24 C13 120.3(4) . . ?
C22 C24 C14 112.0(3) . . ?
C7 C25 H25 120.0 . . ?
C7 C25 C34 120.1(5) . . ?
C34 C25 H25 120.0 . . ?
C7 C26 C9 119.1(4) . . ?
C7 C26 H26 120.5 . . ?
C9 C26 H26 120.5 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C31 H31 121.1 . . ?
C33 C31 C22 117.9(5) . . ?
C33 C31 H31 121.1 . . ?
C31 C33 H33 119.7 . . ?
C31 C33 C35 120.7(5) . . ?
C35 C33 H33 119.7 . . ?
C25 C34 H34 119.7 . . ?
C36 C34 C25 120.5(5) . . ?
C36 C34 H34 119.7 . . ?
C13 C35 C33 121.3(5) . . ?
C13 C35 H35 119.4 . . ?
C33 C35 H35 119.4 . . ?
C9 C36 C16 119.2(3) . . ?
C34 C36 C9 117.7(3) . . ?
C34 C36 C16 123.1(4) . . ?

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
O4 C4 C8 C3 71.9(5) . . . . ?
O4 C4 C8 C6 -170.6(4) . . . . ?
O4 C4 C8 C20 -50.8(5) . . . . ?
N1 C6 C8 C3 -22.2(4) . . . . ?
N1 C6 C8 C4 -134.9(3) . . . . ?
N1 C6 C8 C20 105.0(3) . . . . ?
N1 C6 C18 C1 133.6(3) . . . . ?
N1 C6 C18 C32 -49.0(5) . . . . ?
C1 C4 C8 C3 -106.7(3) . . . . ?
C1 C4 C8 C6 10.9(3) . . . . ?
C1 C4 C8 C20 130.7(3) . . . . ?
C1 C18 C32 C5 0.9(5) . . . . ?
C3 C8 C20 C29 -156.3(4) . . . . ?
C3 C8 C20 C30 28.5(5) . . . . ?
C4 C1 C18 C6 -1.0(4) . . . . ?
C4 C1 C18 C32 -178.8(3) . . . . ?
C4 C1 C28 C11 177.9(4) . . . . ?
C4 C8 C20 C29 -38.1(5) . . . . ?
C4 C8 C20 C30 146.7(4) . . . . ?
C5 C11 C28 C1 0.4(6) . . . . ?
C6 N1 C12 O1 -5.2(6) . . . . ?
C6 N1 C12 C17 174.3(4) . . . . ?
C6 C8 C20 C29 76.9(4) . . . . ?
C6 C8 C20 C30 -98.3(4) . . . . ?
C6 C18 C32 C5 -176.4(3) . . . . ?
C8 C6 C18 C1 7.9(4) . . . . ?
C8 C6 C18 C32 -174.6(3) . . . . ?
C8 C20 C29 C2 -175.3(4) . . . . ?
C8 C20 C30 C15 174.9(4) . . . . ?
C11 C5 C32 C18 -1.3(6) . . . . ?
C12 N1 C6 C8 -89.1(4) . . . . ?
C12 N1 C6 C18 151.1(4) . . . . ?
C18 C1 C4 O4 174.9(4) . . . . ?
C18 C1 C4 C8 -6.5(4) . . . . ?
C18 C1 C28 C11 -0.7(6) . . . . ?
C18 C6 C8 C3 101.8(3) . . . . ?
C18 C6 C8 C4 -10.9(3) . . . . ?
C18 C6 C8 C20 -131.0(3) . . . . ?
C21 C2 C29 C20 0.0(8) . . . . ?
C21 C15 C30 C20 0.4(7) . . . . ?
C28 C1 C4 O4 -3.8(6) . . . . ?
C28 C1 C4 C8 174.7(4) . . . . ?
C28 C1 C18 C6 177.8(3) . . . . ?
C28 C1 C18 C32 0.1(5) . . . . ?
C29 C2 C21 Cl1 178.1(4) . . . . ?
C29 C2 C21 C15 -0.1(8) . . . . ?
C29 C20 C30 C15 -0.4(7) . . . . ?
C30 C15 C21 Cl1 -178.3(4) . . . . ?
C30 C15 C21 C2 -0.1(7) . . . . ?
C30 C20 C29 C2 0.3(7) . . . . ?
C32 C5 C11 C28 0.6(7) . . . . ?
Cl2 C7 C25 C34 -178.8(4) . . . . ?
Cl2 C7 C26 C9 179.3(3) . . . . ?
O3 C19 C22 C24 175.0(4) . . . . ?
O3 C19 C22 C31 -5.0(7) . . . . ?
N2 C14 C16 C19 -135.8(3) . . . . ?
N2 C14 C16 C23 -22.2(4) . . . . ?
N2 C14 C16 C36 107.1(3) . . . . ?
N2 C14 C24 C13 -45.7(5) . . . . ?
N2 C14 C24 C22 136.3(3) . . . . ?
C7 C25 C34 C36 -0.6(7) . . . . ?
C10 N2 C14 C16 -94.2(4) . . . . ?
C10 N2 C14 C24 146.9(4) . . . . ?
C14 N2 C10 O2 0.5(7) . . . . ?
C14 N2 C10 C27 -178.8(4) . . . . ?
C14 C16 C19 O3 -169.1(4) . . . . ?
C14 C16 C19 C22 12.0(4) . . . . ?
C14 C16 C36 C9 55.5(4) . . . . ?
C14 C16 C36 C34 -125.9(4) . . . . ?
C16 C14 C24 C13 -171.6(4) . . . . ?
C16 C14 C24 C22 10.4(4) . . . . ?
C16 C19 C22 C24 -6.1(4) . . . . ?
C16 C19 C22 C31 173.9(4) . . . . ?
C19 C16 C36 C9 -58.6(4) . . . . ?
C19 C16 C36 C34 119.9(4) . . . . ?
C19 C22 C24 C13 178.8(4) . . . . ?
C19 C22 C24 C14 -3.0(4) . . . . ?
C19 C22 C31 C33 -179.2(4) . . . . ?
C22 C31 C33 C35 0.4(8) . . . . ?
C23 C16 C19 O3 73.5(5) . . . . ?
C23 C16 C19 C22 -105.5(4) . . . . ?
C23 C16 C36 C9 -176.4(4) . . . . ?
C23 C16 C36 C34 2.2(5) . . . . ?
C24 C13 C35 C33 0.7(8) . . . . ?
C24 C14 C16 C19 -13.1(4) . . . . ?
C24 C14 C16 C23 100.5(4) . . . . ?
C24 C14 C16 C36 -130.2(3) . . . . ?
C24 C22 C31 C33 0.7(7) . . . . ?
C25 C7 C26 C9 0.3(6) . . . . ?
C25 C34 C36 C9 0.4(6) . . . . ?
C25 C34 C36 C16 -178.2(4) . . . . ?
C26 C7 C25 C34 0.3(7) . . . . ?
C26 C9 C36 C16 178.8(3) . . . . ?
C26 C9 C36 C34 0.2(6) . . . . ?
C31 C22 C24 C13 -1.1(6) . . . . ?
C31 C22 C24 C14 177.0(4) . . . . ?
C31 C33 C35 C13 -1.1(8) . . . . ?
C35 C13 C24 C14 -177.4(4) . . . . ?
C35 C13 C24 C22 0.4(7) . . . . ?
C36 C9 C26 C7 -0.5(6) . . . . ?
C36 C16 C19 O3 -49.2(5) . . . . ?
C36 C16 C19 C22 131.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.882
_oxdiff_exptl_absorpt_empirical_full_min 0.239
####################################################################### 
# 
# 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_huyuehong1-zhfm_0426_auto
_database_code_depnum_ccdc_archive 'CCDC 2408879'
loop_
_audit_author_name
_audit_author_address
'Yuehong hu'
;Lanzhou University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 F2 N O2'
_chemical_formula_sum            'C21 H19 F2 N O2'
_chemical_formula_weight         355.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   9.7705(2)
_cell_length_b                   13.1781(3)
_cell_length_c                   14.4870(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.850(2)
_cell_angle_gamma                90
_cell_volume                     1811.06(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8309
_cell_measurement_temperature    271.8(9)
_cell_measurement_theta_max      76.7210
_cell_measurement_theta_min      4.5580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.11
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12116
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.561
_diffrn_reflns_theta_min         4.598
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      271.8(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00 102.00   0.50    0.05    --   44.44 147.00  85.00   74
  2  ω     62.00 168.00   0.50    0.29    --  112.00 147.00  85.00  212
  3  ω    102.00 127.00   0.50    0.29    --  112.00 124.00 -79.00   50
  4  ω    127.00 152.00   0.50    0.29    --  112.00  61.00-150.00   50
  5  ω     97.00 122.00   0.50    0.29    --  112.00  61.00-150.00   50
  6  ω     44.00  92.00   0.50    0.29    --  112.00 -94.00-120.00   96
  7  ω     50.00  75.00   0.50    0.29    --  112.00-124.00-159.00   50
  8  ω     82.00 107.00   0.50    0.29    --  112.00-125.00 -60.00   50
  9  ω     51.00  77.00   0.50    0.29    --  112.00-125.00 -60.00   52
 10  ω     59.00  84.00   0.50    0.29    --  112.00-147.00  35.00   50
 11  ω     40.00 111.00   0.50    0.29    --  112.00-125.00 150.00  142
 12  ω    -25.00  22.00   0.50    0.05    --   44.44 -19.00   0.00   94
 13  ω    -33.00  12.00   0.50    0.05    --   44.44 -19.00 -60.00   90
 14  ω     58.00 102.00   0.50    0.29    --  112.00 -77.00-180.00   88
 15  ω     56.00  82.00   0.50    0.29    --  112.00 -77.00   0.00   52
 16  ω     39.00  67.00   0.50    0.29    --  112.00 -61.00  30.00   56
 17  ω   -173.00-118.00   0.50    0.29    -- -100.00 -45.00-150.00  110
 18  ω   -136.00 -90.00   0.50    0.29    -- -100.00-147.00  35.00   92
 19  ω   -118.00 -67.00   0.50    0.05    --  -44.44-147.00  35.00  102
 20  ω   -173.00 -90.00   0.50    0.29    -- -100.00 -61.00 -60.00  166
 21  ω    -28.00  25.00   0.50    0.05    --  -44.44  19.00-120.00  106
 22  ω    -53.00 -28.00   0.50    0.29    -- -100.00  45.00  60.00   50
 23  ω    -54.00 -27.00   0.50    0.29    -- -100.00  45.00  90.00   54
 24  ω    -53.00 -27.00   0.50    0.29    -- -100.00  45.00 150.00   52
 25  ω    -95.00 -70.00   0.50    0.05    --  -44.44 147.00  85.00   50
 26  ω   -127.00 -81.00   0.50    0.29    -- -100.00 147.00  85.00   92
 27  ω    -92.00 -67.00   0.50    0.29    -- -100.00 124.00 -79.00   50
 28  ω    -96.00 -46.00   0.50    0.05    --  -44.44 124.00 -79.00  100
 29  ω     74.00 110.00   0.50    0.05    --  112.00-124.00-159.00   72
 30  ω    -44.00 -11.00   0.50    0.05    --  -44.32  37.00-180.00   66
 31  ω      0.00  26.00   0.50    0.05    --  -44.32  37.00-180.00   52
 32  ω    -32.00  10.00   0.50    0.05    --   44.32 -19.00-150.00   84
 33  ω     42.00 123.00   0.50    0.05    --   44.32  19.00  30.00  162
 34  ω      3.00  39.00   0.50    0.05    --   44.32 -37.00 -30.00   72
 35  ω   -103.00 -72.00   0.50    0.05    -- -100.00 125.00  90.00   62
 36  ω   -129.00 -88.00   0.50    0.05    -- -100.00 -61.00 120.00   82
 37  ω    -73.00 -37.00   0.50    0.05    -- -100.00 125.00-120.00   72
 38  ω   -110.00 -85.00   0.50    0.05    -- -100.00 124.00 -79.00   50
 39  ω   -108.00 -60.00   0.50    0.05    -- -100.00 125.00  30.00   96
 40  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00-120.00   52
 41  ω    -57.00 -29.00   0.50    0.05    -- -100.00 125.00  30.00   56
 42  ω   -108.00 -78.00   0.50    0.05    -- -100.00  77.00  90.00   60
 43  ω    -52.00 -26.00   0.50    0.05    -- -100.00 125.00  90.00   52
 44  ω   -173.00-134.00   0.50    0.05    -- -100.00 -61.00 120.00   78
 45  ω    -60.00 -34.00   0.50    0.05    -- -100.00  77.00 -90.00   52
 46  ω   -158.00 -81.00   0.50    0.05    -- -100.00 -30.00  30.00  154
 47  ω   -106.00 -80.00   0.50    0.05    -- -100.00  77.00 -90.00   52
 48  ω    -64.00 -38.00   0.50    0.05    -- -100.00 124.00 -79.00   52
 49  ω    -52.00 -26.00   0.50    0.05    -- -100.00  45.00-150.00   52
 50  ω   -163.00 -83.00   0.50    0.05    -- -100.00-125.00-180.00  160
 51  ω    -67.00 -41.00   0.50    0.05    -- -100.00  77.00  90.00   52
 52  ω     39.00  64.00   0.50    0.05    --  112.00 -61.00 -60.00   50
 53  ω     81.00 106.00   0.50    0.05    --  112.00-125.00  90.00   50
 54  ω     39.00  64.00   0.50    0.05    --  112.00 -61.00-180.00   50
 55  ω     42.00  67.00   0.50    0.05    --  112.00-125.00  90.00   50
 56  ω     39.00  64.00   0.50    0.05    --  112.00 -61.00   0.00   50
 57  ω     66.00  91.00   0.50    0.05    --  112.00 -94.00-150.00   50
 58  ω    142.00 171.00   0.50    0.05    --  112.00  15.00  30.00   58
 59  ω     83.00 109.00   0.50    0.05    --  112.00  15.00  30.00   52
 60  ω     87.00 112.00   0.50    0.05    --  112.00-125.00  30.00   50
 61  ω    149.00 175.00   0.50    0.05    --  112.00  61.00   0.00   52
 62  ω   -117.00 -92.00   0.50    0.05    --  -44.32-147.00  35.00   50
;
_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      -0.0415636000
_diffrn_orient_matrix_UB_12      -0.0602157000
_diffrn_orient_matrix_UB_13      -0.0936833000
_diffrn_orient_matrix_UB_21      0.0381578000
_diffrn_orient_matrix_UB_22      -0.0998134000
_diffrn_orient_matrix_UB_23      0.0555516000
_diffrn_orient_matrix_UB_31      -0.1522878000
_diffrn_orient_matrix_UB_32      -0.0085889000
_diffrn_orient_matrix_UB_33      0.0115641000
_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         0.476
_reflns_Friedel_fraction_full    0.510
_reflns_Friedel_fraction_max     0.463
_reflns_number_gt                2484
_reflns_number_total             2762
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.102
_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)+(0.0720P)²+0.0594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C17(H17), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1309(3) 0.9556(2) 0.3893(2) 0.1391(12) Uani 1 1 d . . . . .
F2 F 0.7717(3) 0.1450(2) 0.6685(2) 0.1350(12) Uani 1 1 d . . . . .
O1 O 0.37612(17) 0.48273(15) 0.37697(14) 0.0662(5) Uani 1 1 d . . . . .
O2 O 0.7432(4) 0.8122(2) 0.6275(3) 0.1434(17) Uani 1 1 d . . . . .
N1 N 0.59883(16) 0.54165(14) 0.40928(12) 0.0468(4) Uani 1 1 d . . . . .
H1 H 0.677302 0.542335 0.392234 0.056 Uiso 1 1 calc R . . . .
C1 C 0.4888(2) 0.49151(16) 0.35459(16) 0.0493(4) Uani 1 1 d . . . . .
C2 C 0.5910(2) 0.59451(16) 0.49557(13) 0.0462(4) Uani 1 1 d . . . . .
H2 H 0.496222 0.583933 0.505336 0.055 Uiso 1 1 calc R . . . .
C3 C 0.4826(2) 0.77504(18) 0.46990(16) 0.0546(5) Uani 1 1 d . . . . .
C4 C 0.6963(2) 0.5565(2) 0.58405(14) 0.0533(5) Uani 1 1 d . . . . .
C5 C 0.6163(2) 0.71132(18) 0.49340(17) 0.0549(5) Uani 1 1 d . . . . .
C6 C 0.7168(2) 0.4476(2) 0.60371(15) 0.0590(6) Uani 1 1 d . . . . .
C7 C 0.2380(3) 0.7967(2) 0.3900(2) 0.0783(8) Uani 1 1 d . . . . .
H7 H 0.153731 0.769982 0.354396 0.094 Uiso 1 1 calc R . . . .
C8 C 0.4856(4) 0.8769(2) 0.4947(3) 0.0790(8) Uani 1 1 d . . . . .
H8 H 0.569088 0.904900 0.530255 0.095 Uiso 1 1 calc R . . . .
C9 C 0.7087(3) 0.7303(2) 0.5936(2) 0.0762(8) Uani 1 1 d . . . . .
C10 C 0.3556(3) 0.7360(2) 0.41699(18) 0.0632(6) Uani 1 1 d . . . . .
H10 H 0.350044 0.667969 0.399560 0.076 Uiso 1 1 calc R . . . .
C11 C 0.6063(3) 0.3795(2) 0.5757(2) 0.0679(6) Uani 1 1 d . . . . .
H11 H 0.518995 0.402947 0.541610 0.081 Uiso 1 1 calc R . . . .
C12 C 0.2466(4) 0.8958(3) 0.4161(2) 0.0854(9) Uani 1 1 d . . . . .
C13 C 0.8475(3) 0.4101(3) 0.65298(18) 0.0734(7) Uani 1 1 d . . . . .
H13 H 0.923013 0.454480 0.672175 0.088 Uiso 1 1 calc R . . . .
C14 C 0.5130(3) 0.4489(3) 0.26405(19) 0.0708(7) Uani 1 1 d . . . . .
H14A H 0.463811 0.385511 0.250235 0.106 Uiso 1 1 calc GR . . . .
H14B H 0.612018 0.438003 0.270799 0.106 Uiso 1 1 calc GR . . . .
H14C H 0.478520 0.495725 0.213037 0.106 Uiso 1 1 calc GR . . . .
C15 C 0.7553(2) 0.6340(2) 0.64010(16) 0.0634(6) Uani 1 1 d . . . . .
C16 C 0.7546(4) 0.2447(3) 0.6468(3) 0.0908(10) Uani 1 1 d . . . . .
C17 C 0.3680(5) 0.9375(3) 0.4680(3) 0.0986(12) Uani 1 1 d . . . . .
H17 H 0.371608 1.005654 0.485195 0.118 Uiso 1 1 calc R . . . .
C18 C 0.7075(3) 0.7393(2) 0.4241(3) 0.0758(7) Uani 1 1 d . . . . .
H18A H 0.790647 0.697807 0.436856 0.114 Uiso 1 1 calc GR . . . .
H18B H 0.734015 0.809459 0.432119 0.114 Uiso 1 1 calc GR . . . .
H18C H 0.654606 0.728043 0.359960 0.114 Uiso 1 1 calc GR . . . .
C19 C 0.8662(4) 0.3080(3) 0.6736(2) 0.0920(12) Uani 1 1 d . . . . .
H19 H 0.953965 0.283124 0.705330 0.110 Uiso 1 1 calc R . . . .
C20 C 0.6238(4) 0.2771(3) 0.5976(3) 0.0829(8) Uani 1 1 d . . . . .
H20 H 0.549258 0.231798 0.579610 0.099 Uiso 1 1 calc R . . . .
C21 C 0.8526(4) 0.6334(3) 0.73768(19) 0.0894(10) Uani 1 1 d . . . . .
H21A H 0.831852 0.575890 0.772609 0.134 Uiso 1 1 calc GR . . . .
H21B H 0.839721 0.694657 0.770494 0.134 Uiso 1 1 calc GR . . . .
H21C H 0.948521 0.629422 0.732266 0.134 Uiso 1 1 calc GR . . . .


_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 C12 1.356(3) . ?
F2 C16 1.352(4) . ?
O1 C1 1.225(3) . ?
O2 C9 1.200(4) . ?
N1 C1 1.346(3) . ?
N1 C2 1.449(3) . ?
C1 C14 1.497(3) . ?
C2 C4 1.523(3) . ?
C2 C5 1.561(3) . ?
C3 C5 1.522(3) . ?
C3 C8 1.389(4) . ?
C3 C10 1.391(3) . ?
C4 C6 1.468(4) . ?
C4 C15 1.345(4) . ?
C5 C9 1.535(4) . ?
C5 C18 1.538(4) . ?
C6 C11 1.387(4) . ?
C6 C13 1.396(3) . ?
C7 C10 1.377(4) . ?
C7 C12 1.358(5) . ?
C8 C17 1.376(5) . ?
C9 C15 1.459(4) . ?
C11 C20 1.388(4) . ?
C12 C17 1.359(5) . ?
C13 C19 1.381(5) . ?
C15 C21 1.503(3) . ?
C16 C19 1.353(6) . ?
C16 C20 1.374(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 122.98(17) . . ?
O1 C1 N1 122.1(2) . . ?
O1 C1 C14 122.4(2) . . ?
N1 C1 C14 115.40(19) . . ?
N1 C2 C4 113.82(18) . . ?
N1 C2 C5 114.55(16) . . ?
C4 C2 C5 105.24(17) . . ?
C8 C3 C5 120.8(2) . . ?
C8 C3 C10 117.4(2) . . ?
C10 C3 C5 121.6(2) . . ?
C6 C4 C2 121.2(2) . . ?
C15 C4 C2 111.4(2) . . ?
C15 C4 C6 127.3(2) . . ?
C3 C5 C2 114.66(17) . . ?
C3 C5 C9 113.6(2) . . ?
C3 C5 C18 108.8(2) . . ?
C9 C5 C2 101.7(2) . . ?
C9 C5 C18 106.1(2) . . ?
C18 C5 C2 111.6(2) . . ?
C11 C6 C4 121.0(2) . . ?
C11 C6 C13 118.3(3) . . ?
C13 C6 C4 120.7(3) . . ?
C12 C7 C10 119.2(3) . . ?
C17 C8 C3 121.6(3) . . ?
O2 C9 C5 125.3(3) . . ?
O2 C9 C15 124.6(3) . . ?
C15 C9 C5 110.0(2) . . ?
C7 C10 C3 121.0(2) . . ?
C6 C11 C20 121.1(3) . . ?
F1 C12 C7 119.2(3) . . ?
F1 C12 C17 118.8(3) . . ?
C7 C12 C17 122.0(3) . . ?
C19 C13 C6 120.9(3) . . ?
C4 C15 C9 109.9(2) . . ?
C4 C15 C21 130.4(3) . . ?
C9 C15 C21 119.7(3) . . ?
F2 C16 C19 119.1(4) . . ?
F2 C16 C20 118.1(4) . . ?
C19 C16 C20 122.9(3) . . ?
C12 C17 C8 118.7(3) . . ?
C16 C19 C13 118.8(3) . . ?
C16 C20 C11 118.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.709
_oxdiff_exptl_absorpt_empirical_full_min 0.400
####################################################################### 
# 
# 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_huyuehong2-zhfm_0426_auto
_database_code_depnum_ccdc_archive 'CCDC 2408877'
loop_
_audit_author_name
_audit_author_address
'Yuehong hu'
;Lanzhou University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 F N O2'
_chemical_formula_sum            'C18 H16 F N O2'
_chemical_formula_weight         297.32
_chemical_melting_point          ?
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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.35635(9)
_cell_length_b                   20.16774(19)
_cell_length_c                   9.47069(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.5299(12)
_cell_angle_gamma                90
_cell_volume                     1484.72(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15574
_cell_measurement_temperature    271.7(3)
_cell_measurement_theta_max      77.3290
_cell_measurement_theta_min      2.1510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19065
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.494
_diffrn_reflns_theta_min         6.054
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      271.7(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    100.00 175.00   0.50    0.05    --  112.00  61.00-180.00  150
  2  ω    143.00 173.00   0.50    0.05    --  112.00  45.00 -90.00   60
  3  ω    101.00 127.00   0.50    0.05    --  112.00  45.00 -90.00   52
  4  ω     92.00 175.00   0.50    0.05    --  112.00  61.00   0.00  166
  5  ω     99.00 171.00   0.50    0.05    --  112.00  77.00  60.00  144
  6  ω    -25.00  20.00   0.50    0.05    --   44.32 -19.00   0.00   90
  7  ω    -25.00  16.00   0.50    0.05    --   44.32 -19.00 120.00   82
  8  ω     74.00 115.00   0.50    0.05    --   44.32-159.00  41.00   82
  9  ω     91.00 134.00   0.50    0.05    --  112.00-159.00  41.00   86
 10  ω     82.00 112.00   0.50    0.05    --  112.00-125.00 120.00   60
 11  ω     43.00  77.00   0.50    0.05    --  112.00-125.00 120.00   68
 12  ω     44.00  78.00   0.50    0.05    --  112.00-159.00  41.00   68
 13  ω     40.00  98.00   0.50    0.05    --  112.00 -94.00   0.00  116
 14  ω    -29.00  -4.00   0.50    0.05    --   44.32 -19.00-180.00   50
 15  ω     29.00  54.00   0.50    0.05    --   44.32-118.00-165.00   50
 16  ω     44.00  79.00   0.50    0.05    --  112.00-125.00-150.00   70
 17  ω     50.00  75.00   0.50    0.05    --  112.00-118.00-165.00   50
 18  ω     42.00  67.00   0.50    0.05    --  112.00 -61.00-180.00   50
 19  ω     41.00  89.00   0.50    0.05    --  112.00 -77.00-180.00   96
 20  ω     39.00  91.00   0.50    0.05    --  112.00 -77.00 -60.00  104
 21  ω     65.00 100.00   0.50    0.05    --  112.00 -77.00   0.00   70
 22  ω     39.00  99.00   0.50    0.05    --  112.00 -77.00  60.00  120
 23  ω     43.00  68.00   0.50    0.05    --  112.00 -61.00  90.00   50
 24  ω     40.00  65.00   0.50    0.05    --  112.00 -61.00-150.00   50
 25  ω     81.00 136.00   0.50    0.05    --  112.00 118.00 -78.00  110
 26  ω     82.00 107.00   0.50    0.05    --  112.00 159.00  73.00   50
 27  ω     53.00  80.00   0.50    0.05    --   44.32 159.00  73.00   54
 28  ω    -22.00  28.00   0.50    0.05    --  -44.32  19.00  30.00  100
 29  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
 30  ω     -3.00  35.00   0.50    0.05    --  -44.32  19.00  60.00   76
 31  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 150.00   58
 32  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00  90.00   58
 33  ω    -70.00 -26.00   0.50    0.05    -- -100.00  61.00  30.00   88
 34  ω    -68.00 -43.00   0.50    0.05    -- -100.00 118.00 -78.00   50
 35  ω   -126.00 -55.00   0.50    0.05    -- -100.00 146.00-158.55  142
 36  ω    -96.00 -71.00   0.50    0.05    --  -44.32 159.00  73.00   50
 37  ω   -121.00 -87.00   0.50    0.05    -- -100.00 148.00 125.80   68
 38  ω    -65.00 -36.00   0.50    0.05    -- -100.00 148.00 125.80   58
 39  ω   -126.00 -33.00   0.50    0.05    -- -100.00 144.00  97.24  186
 40  ω   -111.00 -86.00   0.50    0.05    -- -100.00 159.00  73.00   50
 41  ω    -58.00 -32.00   0.50    0.05    -- -100.00 125.00 -30.00   52
 42  ω   -108.00 -80.00   0.50    0.05    -- -100.00 125.00 -30.00   56
 43  ω    -92.00 -19.00   0.50    0.05    --  -44.32 118.00 -78.00  146
 44  ω    -55.00 -28.00   0.50    0.05    -- -100.00 125.00-150.00   54
 45  ω   -112.00 -59.00   0.50    0.05    -- -100.00 125.00-150.00  106
 46  ω   -177.00-101.00   0.50    0.05    -- -100.00 -30.00  90.00  152
 47  ω   -118.00 -29.00   0.50    0.05    --  -44.32 -57.00  90.00  178
 48  ω    -88.00 -59.00   0.50    0.05    --  -44.32-159.00  41.00   58
 49  ω   -125.00 -99.00   0.50    0.05    -- -100.00-159.00  41.00   52
 50  ω   -130.00 -97.00   0.50    0.05    -- -100.00-118.00-165.00   66
 51  ω   -172.00-147.00   0.50    0.05    -- -100.00-118.00-165.00   50
;
_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      -0.1248558000
_diffrn_orient_matrix_UB_12      -0.0401845000
_diffrn_orient_matrix_UB_13      0.0524996000
_diffrn_orient_matrix_UB_21      0.0542760000
_diffrn_orient_matrix_UB_22      -0.0640771000
_diffrn_orient_matrix_UB_23      -0.0589483000
_diffrn_orient_matrix_UB_31      0.1440402000
_diffrn_orient_matrix_UB_32      -0.0106704000
_diffrn_orient_matrix_UB_33      0.1560396000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2882
_reflns_number_total             3061
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.084
_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)+(0.0683P)²+0.2604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_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
F1 F 0.44521(10) 0.39113(4) 0.41083(9) 0.0566(2) Uani 1 1 d . . . . .
O1 O 0.23372(12) 0.24882(5) 0.65853(9) 0.0525(3) Uani 1 1 d . . . . .
O2 O 0.06430(13) 0.47803(5) 0.24914(11) 0.0557(3) Uani 1 1 d . . . . .
N1 N 0.05802(12) 0.25454(5) 0.41414(10) 0.0385(2) Uani 1 1 d . . . . .
H1 H -0.035194 0.240438 0.345344 0.046 Uiso 1 1 calc R U . . .
C1 C 0.11126(14) 0.22680(6) 0.55239(12) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.15307(14) 0.30762(5) 0.37728(12) 0.0352(2) Uani 1 1 d . . . . .
H2 H 0.276143 0.299603 0.431699 0.042 Uiso 1 1 calc R U . . .
C3 C 0.25962(15) 0.41168(5) 0.54263(13) 0.0392(3) Uani 1 1 d . . . . .
C4 C 0.11122(15) 0.38042(5) 0.41326(12) 0.0366(3) Uani 1 1 d . . . . .
C5 C 0.11820(14) 0.30770(6) 0.20880(12) 0.0395(3) Uani 1 1 d . . . . .
C6 C 0.07701(15) 0.37019(6) 0.14571(13) 0.0426(3) Uani 1 1 d . . . . .
C7 C 0.08196(15) 0.41848(6) 0.26374(13) 0.0405(3) Uani 1 1 d . . . . .
C8 C 0.42266(17) 0.41504(6) 0.53684(14) 0.0446(3) Uani 1 1 d . . . . .
C9 C -0.06029(16) 0.38350(7) 0.43742(15) 0.0482(3) Uani 1 1 d . . . . .
H9A H -0.050830 0.359055 0.527116 0.072 Uiso 1 1 calc R U . . .
H9B H -0.149453 0.364504 0.351262 0.072 Uiso 1 1 calc R U . . .
H9C H -0.087961 0.428876 0.449028 0.072 Uiso 1 1 calc R U . . .
C10 C 0.2424(2) 0.43955(7) 0.67065(15) 0.0515(3) Uani 1 1 d . . . . .
H10 H 0.135582 0.439192 0.680357 0.062 Uiso 1 1 calc R U . . .
C11 C 0.01366(19) 0.16663(7) 0.56851(16) 0.0544(3) Uani 1 1 d . . . . .
H11A H -0.027994 0.173532 0.649308 0.082 Uiso 1 1 calc R U . . .
H11B H 0.088395 0.128737 0.591210 0.082 Uiso 1 1 calc R U . . .
H11C H -0.081831 0.159124 0.475331 0.082 Uiso 1 1 calc R U . . .
C12 C 0.12485(19) 0.25410(7) 0.11932(15) 0.0506(3) Uani 1 1 d . . . . .
H12 H 0.152275 0.211917 0.160880 0.061 Uiso 1 1 calc R U . . .
C13 C 0.03989(19) 0.38127(8) -0.00852(15) 0.0562(4) Uani 1 1 d . . . . .
H13 H 0.011527 0.423340 -0.050516 0.067 Uiso 1 1 calc R U . . .
C14 C 0.56423(19) 0.44189(7) 0.64860(18) 0.0588(4) Uani 1 1 d . . . . .
H14 H 0.671351 0.441895 0.639555 0.071 Uiso 1 1 calc R U . . .
C15 C 0.0468(2) 0.32760(9) -0.09656(15) 0.0659(4) Uani 1 1 d . . . . .
H15 H 0.022246 0.333514 -0.199783 0.079 Uiso 1 1 calc R U . . .
C16 C 0.0896(2) 0.26505(9) -0.03350(17) 0.0630(4) Uani 1 1 d . . . . .
H16 H 0.094741 0.229767 -0.094927 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3828(3) 0.46797(8) 0.78447(16) 0.0674(5) Uani 1 1 d . . . . .
H17 H 0.368212 0.486708 0.868683 0.081 Uiso 1 1 calc R U . . .
C18 C 0.5429(2) 0.46873(8) 0.77407(18) 0.0697(5) Uani 1 1 d . . . . .
H18 H 0.636057 0.487287 0.851474 0.084 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
F1 C8 1.3628(15) . ?
O1 C1 1.2247(14) . ?
O2 C7 1.2117(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.3407(14) . ?
N1 C2 1.4499(14) . ?
C1 C11 1.5009(17) . ?
C2 H2 0.9800 . ?
C2 C4 1.5753(15) . ?
C2 C5 1.5132(15) . ?
C3 C4 1.5236(16) . ?
C3 C8 1.3852(18) . ?
C3 C10 1.3910(17) . ?
C4 C7 1.5492(15) . ?
C4 C9 1.5333(16) . ?
C5 C6 1.3829(17) . ?
C5 C12 1.3873(18) . ?
C6 C7 1.4718(17) . ?
C6 C13 1.3955(17) . ?
C8 C14 1.3762(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C17 1.392(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C16 1.385(2) . ?
C13 H13 0.9300 . ?
C13 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C14 C18 1.376(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.377(3) . ?
C18 H18 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
C1 N1 H1 119.1 . . ?
C1 N1 C2 121.90(9) . . ?
C2 N1 H1 119.1 . . ?
O1 C1 N1 121.88(11) . . ?
O1 C1 C11 122.09(10) . . ?
N1 C1 C11 116.02(10) . . ?
N1 C2 H2 108.3 . . ?
N1 C2 C4 116.83(9) . . ?
N1 C2 C5 110.13(9) . . ?
C4 C2 H2 108.3 . . ?
C5 C2 H2 108.3 . . ?
C5 C2 C4 104.77(9) . . ?
C8 C3 C4 120.70(11) . . ?
C8 C3 C10 115.65(12) . . ?
C10 C3 C4 123.64(12) . . ?
C3 C4 C2 112.32(9) . . ?
C3 C4 C7 109.81(9) . . ?
C3 C4 C9 113.12(10) . . ?
C7 C4 C2 103.72(9) . . ?
C9 C4 C2 111.34(9) . . ?
C9 C4 C7 105.89(9) . . ?
C6 C5 C2 112.19(10) . . ?
C6 C5 C12 120.37(11) . . ?
C12 C5 C2 127.44(11) . . ?
C5 C6 C7 109.98(10) . . ?
C5 C6 C13 121.52(12) . . ?
C13 C6 C7 128.50(12) . . ?
O2 C7 C4 124.56(11) . . ?
O2 C7 C6 126.94(11) . . ?
C6 C7 C4 108.50(10) . . ?
F1 C8 C3 118.13(11) . . ?
F1 C8 C14 117.17(13) . . ?
C14 C8 C3 124.69(13) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10 119.5 . . ?
C3 C10 C17 120.91(15) . . ?
C17 C10 H10 119.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12 120.9 . . ?
C16 C12 C5 118.25(14) . . ?
C16 C12 H12 120.9 . . ?
C6 C13 H13 121.2 . . ?
C15 C13 C6 117.65(14) . . ?
C15 C13 H13 121.2 . . ?
C8 C14 H14 120.9 . . ?
C18 C14 C8 118.15(15) . . ?
C18 C14 H14 120.9 . . ?
C13 C15 H15 119.5 . . ?
C13 C15 C16 121.01(13) . . ?
C16 C15 H15 119.5 . . ?
C12 C16 C15 121.20(14) . . ?
C12 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C10 C17 H17 119.5 . . ?
C18 C17 C10 120.93(15) . . ?
C18 C17 H17 119.5 . . ?
C14 C18 C17 119.66(14) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 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
F1 C8 C14 C18 177.44(13) . . . . ?
N1 C2 C4 C3 111.06(11) . . . . ?
N1 C2 C4 C7 -130.43(9) . . . . ?
N1 C2 C4 C9 -16.98(13) . . . . ?
N1 C2 C5 C6 131.44(11) . . . . ?
N1 C2 C5 C12 -48.98(16) . . . . ?
C1 N1 C2 C4 -86.94(13) . . . . ?
C1 N1 C2 C5 153.74(11) . . . . ?
C2 N1 C1 O1 6.90(18) . . . . ?
C2 N1 C1 C11 -172.17(11) . . . . ?
C2 C4 C7 O2 -171.82(12) . . . . ?
C2 C4 C7 C6 9.04(12) . . . . ?
C2 C5 C6 C7 0.77(14) . . . . ?
C2 C5 C6 C13 -179.90(11) . . . . ?
C2 C5 C12 C16 -179.45(12) . . . . ?
C3 C4 C7 O2 -51.59(16) . . . . ?
C3 C4 C7 C6 129.28(10) . . . . ?
C3 C8 C14 C18 -1.5(2) . . . . ?
C3 C10 C17 C18 -0.6(2) . . . . ?
C4 C2 C5 C6 5.01(13) . . . . ?
C4 C2 C5 C12 -175.41(12) . . . . ?
C4 C3 C8 F1 1.59(16) . . . . ?
C4 C3 C8 C14 -179.52(12) . . . . ?
C4 C3 C10 C17 -179.37(12) . . . . ?
C5 C2 C4 C3 -126.79(10) . . . . ?
C5 C2 C4 C7 -8.27(11) . . . . ?
C5 C2 C4 C9 105.18(10) . . . . ?
C5 C6 C7 O2 174.46(12) . . . . ?
C5 C6 C7 C4 -6.43(14) . . . . ?
C5 C6 C13 C15 -0.4(2) . . . . ?
C5 C12 C16 C15 -0.7(2) . . . . ?
C6 C5 C12 C16 0.10(19) . . . . ?
C6 C13 C15 C16 -0.2(2) . . . . ?
C7 C6 C13 C15 178.77(13) . . . . ?
C8 C3 C4 C2 54.98(14) . . . . ?
C8 C3 C4 C7 -59.89(14) . . . . ?
C8 C3 C4 C9 -177.93(11) . . . . ?
C8 C3 C10 C17 -0.67(19) . . . . ?
C8 C14 C18 C17 0.1(2) . . . . ?
C9 C4 C7 O2 70.86(15) . . . . ?
C9 C4 C7 C6 -108.28(11) . . . . ?
C10 C3 C4 C2 -126.39(12) . . . . ?
C10 C3 C4 C7 118.74(12) . . . . ?
C10 C3 C4 C9 0.70(16) . . . . ?
C10 C3 C8 F1 -177.15(11) . . . . ?
C10 C3 C8 C14 1.74(19) . . . . ?
C10 C17 C18 C14 0.9(3) . . . . ?
C12 C5 C6 C7 -178.85(11) . . . . ?
C12 C5 C6 C13 0.48(19) . . . . ?
C13 C6 C7 O2 -4.8(2) . . . . ?
C13 C6 C7 C4 174.31(13) . . . . ?
C13 C15 C16 C12 0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.905
_oxdiff_exptl_absorpt_empirical_full_min 0.618
####################################################################### 
# 
# 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_huyh_1211_auto
_database_code_depnum_ccdc_archive 'CCDC 2410041'
loop_
_audit_author_name
_audit_author_address
'Yuehong hu'
;Lanzhou University
China
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br2 N O2'
_chemical_formula_sum            'C21 H19 Br2 N O2'
_chemical_formula_weight         477.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.9874(2)
_cell_length_b                   9.81932(13)
_cell_length_c                   24.6758(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.0437(14)
_cell_angle_gamma                90
_cell_volume                     3890.75(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10373
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.8830
_cell_measurement_theta_min      3.7870
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.345
_exptl_absorpt_coefficient_mu    5.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (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    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.096
_diffrn_reflns_theta_min         3.790
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 120.00   58
  2  ω    -52.00 -25.00   0.50    0.05    -- -100.00  45.00  60.00   54
  3  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00   0.00   50
  4  ω    -50.00 -25.00   0.50    0.05    -- -100.00  45.00  30.00   50
  5  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 -30.00   58
  6  ω    -74.00 -32.00   0.50    0.05    -- -100.00  61.00-120.00   84
  7  ω    -44.00  27.00   0.50    0.05    --  -44.63  37.00 120.00  142
  8  ω    -33.00  23.00   0.50    0.05    --   44.63 -19.00 -30.00  112
  9  ω    -31.00  39.00   0.50    0.05    --   44.63 -37.00-120.00  140
 10  ω     43.00  68.00   0.50    0.05    --  108.93 -61.00-150.00   50
 11  ω     69.00 107.00   0.50    0.05    --   44.63 145.00  39.00   76
 12  ω     83.00 131.00   0.50    0.05    --  108.93 126.00-128.00   96
 13  ω    135.00 169.00   0.50    0.05    --  108.93 126.00-128.00   68
 14  ω    144.00 175.00   0.50    0.05    --  108.93  61.00-150.00   62
 15  ω     92.00 129.00   0.50    0.05    --  108.93  61.00-150.00   74
 16  ω     96.00 160.00   0.50    0.05    --  108.93  45.00  30.00  128
 17  ω     37.00  64.00   0.50    0.05    --  108.93 -94.00 150.00   54
 18  ω     50.00  75.00   0.50    0.05    --  108.93-126.00 153.00   50
 19  ω     56.00 125.00   0.50    0.05    --  108.93-145.00 -13.00  138
 20  ω     70.00 101.00   0.50    0.05    --  108.93 -94.00 -60.00   62
 21  ω    -71.00 -46.00   0.50    0.05    --  -44.63 145.00  39.00   50
 22  ω    -92.00 -66.00   0.50    0.05    -- -100.00 137.00 116.16   52
 23  ω   -120.00 -95.00   0.50    0.05    -- -100.00 137.00 116.16   50
 24  ω   -112.00 -65.00   0.50    0.05    -- -100.00 125.00 150.00   94
 25  ω    -65.00 -39.00   0.50    0.05    -- -100.00 125.00 120.00   52
 26  ω   -110.00 -76.00   0.50    0.05    -- -100.00 125.00 120.00   68
 27  ω   -105.00 -79.00   0.50    0.05    -- -100.00 145.00  39.00   52
 28  ω    -95.00 -59.00   0.50    0.05    --  -44.63 126.00-128.00   72
;
_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      -0.0037191000
_diffrn_orient_matrix_UB_12      -0.1526496000
_diffrn_orient_matrix_UB_13      -0.0150533000
_diffrn_orient_matrix_UB_21      0.0428617000
_diffrn_orient_matrix_UB_22      -0.0346228000
_diffrn_orient_matrix_UB_23      0.0637604000
_diffrn_orient_matrix_UB_31      -0.0857509000
_diffrn_orient_matrix_UB_32      -0.0106764000
_diffrn_orient_matrix_UB_33      0.0084070000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3623
_reflns_number_total             3856
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.775
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+12.0932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.63864(2) 0.64313(5) 0.99733(2) 0.05195(16) Uani 1 1 d . . . . .
Br2 Br 0.08193(2) 0.68436(4) 0.50242(2) 0.04780(15) Uani 1 1 d . . . . .
O1 O 0.56323(12) 0.2439(2) 0.74543(9) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.25475(12) 0.40751(19) 0.80564(8) 0.0295(4) Uani 1 1 d . . . . .
N1 N 0.34179(12) 0.5047(2) 0.76416(8) 0.0178(4) Uani 1 1 d . . . . .
H1 H 0.3677(18) 0.569(3) 0.7623(13) 0.019(7) Uiso 1 1 d . . . . .
C1 C 0.44888(15) 0.3125(2) 0.77867(11) 0.0215(5) Uani 1 1 d . . . . .
C2 C 0.36416(14) 0.3790(2) 0.74217(10) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.318546 0.311254 0.737841 0.022 Uiso 1 1 calc R U . . .
C3 C 0.37347(15) 0.4028(2) 0.68374(10) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.44700(16) 0.3606(2) 0.68053(11) 0.0240(5) Uani 1 1 d . . . . .
C5 C 0.49589(15) 0.3008(2) 0.73548(11) 0.0242(5) Uani 1 1 d . . . . .
C6 C 0.49740(15) 0.3945(2) 0.83148(10) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.46456(16) 0.4104(3) 0.87618(11) 0.0277(5) Uani 1 1 d . . . . .
H7 H 0.412873 0.368674 0.873230 0.033 Uiso 1 1 calc R U . . .
C8 C 0.50554(17) 0.4854(3) 0.92456(11) 0.0331(6) Uani 1 1 d . . . . .
H8 H 0.481078 0.498416 0.953739 0.040 Uiso 1 1 calc R U . . .
C9 C 0.58228(16) 0.5413(3) 0.93009(11) 0.0324(6) Uani 1 1 d . . . . .
C10 C 0.61749(16) 0.5275(3) 0.88715(12) 0.0316(6) Uani 1 1 d . . . . .
H10 H 0.670189 0.566852 0.891142 0.038 Uiso 1 1 calc R U . . .
C11 C 0.57432(16) 0.4551(3) 0.83803(11) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.597776 0.446616 0.808114 0.031 Uiso 1 1 calc R U . . .
C12 C 0.43375(18) 0.1668(3) 0.79612(13) 0.0317(6) Uani 1 1 d . . . . .
H12A H 0.487237 0.119874 0.812265 0.048 Uiso 1 1 calc R U . . .
H12B H 0.398986 0.117157 0.762328 0.048 Uiso 1 1 calc R U . . .
H12C H 0.405393 0.170631 0.824889 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4795(2) 0.3616(3) 0.63078(13) 0.0337(6) Uani 1 1 d . . . . .
H13A H 0.435726 0.393432 0.596347 0.051 Uiso 1 1 calc R U . . .
H13B H 0.496393 0.269224 0.624277 0.051 Uiso 1 1 calc R U . . .
H13C H 0.527613 0.422705 0.639236 0.051 Uiso 1 1 calc R U . . .
C14 C 0.30448(16) 0.4669(3) 0.63806(10) 0.0233(5) Uani 1 1 d . . . . .
C15 C 0.22476(17) 0.4107(3) 0.62204(12) 0.0309(6) Uani 1 1 d . . . . .
H15 H 0.215673 0.328962 0.639751 0.037 Uiso 1 1 calc R U . . .
C16 C 0.15865(18) 0.4722(3) 0.58069(12) 0.0348(6) Uani 1 1 d . . . . .
H16 H 0.104739 0.432378 0.569364 0.042 Uiso 1 1 calc R U . . .
C17 C 0.17258(17) 0.5924(3) 0.55626(11) 0.0319(6) Uani 1 1 d . . . . .
C18 C 0.25057(19) 0.6504(3) 0.57093(11) 0.0325(6) Uani 1 1 d . . . . .
H18 H 0.258991 0.732821 0.553434 0.039 Uiso 1 1 calc R U . . .
C19 C 0.31674(17) 0.5865(3) 0.61170(11) 0.0280(5) Uani 1 1 d . . . . .
H19 H 0.370933 0.624915 0.621659 0.034 Uiso 1 1 calc R U . . .
C20 C 0.29057(14) 0.5086(3) 0.79595(10) 0.0214(5) Uani 1 1 d . . . . .
C21 C 0.28129(19) 0.6465(3) 0.81987(13) 0.0328(6) Uani 1 1 d . . . . .
H21A H 0.223024 0.675677 0.804567 0.049 Uiso 1 1 calc R U . . .
H21B H 0.316636 0.712467 0.808838 0.049 Uiso 1 1 calc R U . . .
H21C H 0.298185 0.641198 0.861769 0.049 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
Br1 C9 1.906(3) . ?
Br2 C17 1.902(3) . ?
O1 C5 1.224(3) . ?
O2 C20 1.228(3) . ?
N1 H1 0.78(3) . ?
N1 C2 1.449(3) . ?
N1 C20 1.349(3) . ?
C1 C2 1.569(3) . ?
C1 C5 1.530(3) . ?
C1 C6 1.525(3) . ?
C1 C12 1.540(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.519(3) . ?
C3 C4 1.343(3) . ?
C3 C14 1.476(3) . ?
C4 C5 1.462(4) . ?
C4 C13 1.501(3) . ?
C6 C7 1.398(3) . ?
C6 C11 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.395(4) . ?
C14 C19 1.390(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(4) . ?
C17 C18 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.506(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 117(2) . . ?
C20 N1 H1 120(2) . . ?
C20 N1 C2 122.7(2) . . ?
C5 C1 C2 102.76(19) . . ?
C5 C1 C12 107.3(2) . . ?
C6 C1 C2 114.17(19) . . ?
C6 C1 C5 112.1(2) . . ?
C6 C1 C12 110.2(2) . . ?
C12 C1 C2 110.0(2) . . ?
N1 C2 C1 116.31(19) . . ?
N1 C2 H2 108.6 . . ?
N1 C2 C3 110.20(19) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 104.41(18) . . ?
C3 C2 H2 108.6 . . ?
C4 C3 C2 113.3(2) . . ?
C4 C3 C14 127.5(2) . . ?
C14 C3 C2 119.2(2) . . ?
C3 C4 C5 109.1(2) . . ?
C3 C4 C13 130.1(3) . . ?
C5 C4 C13 120.8(2) . . ?
O1 C5 C1 124.1(2) . . ?
O1 C5 C4 125.5(2) . . ?
C4 C5 C1 110.4(2) . . ?
C7 C6 C1 119.3(2) . . ?
C11 C6 C1 123.3(2) . . ?
C11 C6 C7 117.4(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 Br1 119.0(2) . . ?
C8 C9 C10 121.1(3) . . ?
C10 C9 Br1 119.9(2) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.7(2) . . ?
C11 C10 H10 120.6 . . ?
C6 C11 H11 119.1 . . ?
C10 C11 C6 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C3 120.2(2) . . ?
C19 C14 C3 121.0(2) . . ?
C19 C14 C15 118.8(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Br2 119.7(2) . . ?
C18 C17 Br2 118.5(2) . . ?
C18 C17 C16 121.7(3) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
O2 C20 N1 123.0(2) . . ?
O2 C20 C21 121.9(2) . . ?
N1 C20 C21 115.0(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C9 C10 C11 -178.7(2) . . . . ?
Br2 C17 C18 C19 177.8(2) . . . . ?
N1 C2 C3 C4 126.4(2) . . . . ?
N1 C2 C3 C14 -53.6(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C14 -179.2(2) . . . . ?
C1 C6 C7 C8 -179.0(2) . . . . ?
C1 C6 C11 C10 -179.0(2) . . . . ?
C2 N1 C20 O2 -4.8(4) . . . . ?
C2 N1 C20 C21 174.2(2) . . . . ?
C2 C1 C5 O1 -174.1(2) . . . . ?
C2 C1 C5 C4 3.0(3) . . . . ?
C2 C1 C6 C7 66.2(3) . . . . ?
C2 C1 C6 C11 -114.2(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C13 177.9(2) . . . . ?
C2 C3 C14 C15 -55.3(3) . . . . ?
C2 C3 C14 C19 122.4(2) . . . . ?
C3 C4 C5 O1 174.4(2) . . . . ?
C3 C4 C5 C1 -2.7(3) . . . . ?
C3 C14 C15 C16 177.7(2) . . . . ?
C3 C14 C19 C18 -176.5(2) . . . . ?
C4 C3 C14 C15 124.7(3) . . . . ?
C4 C3 C14 C19 -57.6(4) . . . . ?
C5 C1 C2 N1 -123.9(2) . . . . ?
C5 C1 C2 C3 -2.2(2) . . . . ?
C5 C1 C6 C7 -177.5(2) . . . . ?
C5 C1 C6 C11 2.1(3) . . . . ?
C6 C1 C2 N1 -2.3(3) . . . . ?
C6 C1 C2 C3 119.3(2) . . . . ?
C6 C1 C5 O1 62.9(3) . . . . ?
C6 C1 C5 C4 -120.0(2) . . . . ?
C6 C7 C8 C9 -2.8(4) . . . . ?
C7 C6 C11 C10 0.6(4) . . . . ?
C7 C8 C9 Br1 -179.4(2) . . . . ?
C7 C8 C9 C10 2.3(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C6 -1.0(4) . . . . ?
C11 C6 C7 C8 1.3(4) . . . . ?
C12 C1 C2 N1 122.1(2) . . . . ?
C12 C1 C2 C3 -116.2(2) . . . . ?
C12 C1 C5 O1 -58.2(3) . . . . ?
C12 C1 C5 C4 118.9(2) . . . . ?
C12 C1 C6 C7 -58.2(3) . . . . ?
C12 C1 C6 C11 121.5(3) . . . . ?
C13 C4 C5 O1 -2.8(4) . . . . ?
C13 C4 C5 C1 -179.8(2) . . . . ?
C14 C3 C4 C5 -178.9(2) . . . . ?
C14 C3 C4 C13 -2.0(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C15 C16 C17 Br2 -176.6(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 -1.0(4) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
C20 N1 C2 C1 -96.4(3) . . . . ?
C20 N1 C2 C3 145.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.113
_oxdiff_exptl_absorpt_empirical_full_min 0.394
