# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_10666
_database_code_depnum_ccdc_archive 'CCDC 1957349'
loop_
_audit_author_name
_audit_author_address
'Hai-Lei Cui'
;Chongqing University of Arts and Sciences
China
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Cl N O4'
_chemical_formula_sum            'C22 H19 Cl N O4'
_chemical_formula_weight         396.83
_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      tetragonal
_space_group_IT_number           106
_space_group_name_H-M_alt        'P 42 b c'
_space_group_name_Hall           'P 4c -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'

_cell_length_a                   16.7456(5)
_cell_length_b                   16.7456(5)
_cell_length_c                   13.5915(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3811.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5360
_cell_measurement_theta_min      3.7700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16477
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.616
_diffrn_reflns_theta_min         3.733
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -80.00   1.00    2.50    --  -33.50 -19.00-120.00   25
  2  ω    -21.00   4.00   1.00    2.50    --  -33.50 -19.00-120.00   25
  3  ω     18.00  97.00   1.00    2.50    --   36.80  57.00-150.00   79
  4  ω    -31.00  48.00   1.00    2.50    --   36.80 -57.00  30.00   79
  5  ω     19.00  45.00   1.00    2.50    --   36.80-125.00 -30.00   26
  6  ω      9.00  38.00   1.00    2.50    --   36.80  77.00  60.00   29
  7  ω     73.00  99.00   1.00    2.50    --   36.80  77.00  60.00   26
  8  ω     53.00  91.00   1.00    2.50    --   36.80-125.00 -30.00   38
  9  ω    -31.00  52.00   1.00    2.50    --   36.80 -57.00 -30.00   83
 10  ω     18.00  95.00   1.00    2.50    --   36.80  57.00 150.00   77
 11  ω     58.00  83.00   1.00    2.50    --   36.80  57.00  30.00   25
 12  ω     39.00 143.00   1.00    2.50    --  108.00 -91.00 -90.00  104
 13  ω    140.00 173.00   1.00    2.50    --  108.00  50.00 -60.00   33
 14  ω    103.00 160.00   1.00    2.50    --  108.00 111.00-150.00   57
 15  ω    102.00 128.00   1.00    2.50    --  108.00  50.00 -60.00   26
 16  ω     89.00 163.00   1.00    2.50    --  108.00  50.00-180.00   74
 17  ω    109.00 139.00   1.00    2.50    --  108.00 111.00  60.00   30
 18  ω     94.00 153.00   1.00    2.50    --  108.00  50.00-150.00   59
 19  ω     47.00 118.00   1.00    2.50    --  108.00 -63.00  90.00   71
 20  ω     61.00 115.00   1.00    2.50    --  108.00-111.00  90.00   54
 21  ω     39.00 106.00   1.00    2.50    --  108.00 -50.00-120.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640146000
_diffrn_orient_matrix_UB_12      0.0597557000
_diffrn_orient_matrix_UB_13      0.0345263000
_diffrn_orient_matrix_UB_21      0.0647870000
_diffrn_orient_matrix_UB_22      -0.0489074000
_diffrn_orient_matrix_UB_23      -0.0534431000
_diffrn_orient_matrix_UB_31      -0.0132651000
_diffrn_orient_matrix_UB_32      0.0500148000
_diffrn_orient_matrix_UB_33      -0.0937388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.728
_reflns_Friedel_fraction_max     0.689
_reflns_number_gt                2121
_reflns_number_total             3207
_reflns_odcompleteness_completeness 99.90
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.159
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_coef       0.00132(14)
_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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      0.994
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.96402(8) 0.38117(9) 0.26486(12) 0.0838(5) Uani 1 1 d . . . . .
O1 O 0.6311(2) 0.3347(2) 0.4007(3) 0.0777(12) Uani 1 1 d . . . . .
O2 O 0.5047(2) 0.3674(3) 0.4035(5) 0.1090(17) Uani 1 1 d . . . . .
O3 O 0.87065(19) 0.80058(19) 0.6804(3) 0.0629(10) Uani 1 1 d . . . . .
O4 O 0.93220(17) 0.67508(19) 0.5989(3) 0.0564(9) Uani 1 1 d . . . . .
N1 N 0.5850(2) 0.5636(2) 0.5704(3) 0.0518(10) Uani 1 1 d . . . . .
C1 C 0.8824(2) 0.4151(3) 0.3346(4) 0.0497(12) Uani 1 1 d . . . . .
C2 C 0.8507(3) 0.3661(3) 0.4050(4) 0.0560(13) Uani 1 1 d . . . . .
H2 H 0.873432 0.316537 0.418151 0.067 Uiso 1 1 calc R . . . .
C3 C 0.7848(3) 0.3917(3) 0.4560(4) 0.0533(12) Uani 1 1 d . . . . .
H3 H 0.763519 0.359159 0.504832 0.064 Uiso 1 1 calc R . . . .
C4 C 0.7488(2) 0.4646(3) 0.4368(3) 0.0444(11) Uani 1 1 d . . . . .
C5 C 0.6744(2) 0.4907(3) 0.4881(3) 0.0462(11) Uani 1 1 d . . . . .
C6 C 0.6647(2) 0.5583(3) 0.5455(4) 0.0473(11) Uani 1 1 d . . . . .
C7 C 0.5437(2) 0.5017(3) 0.5292(4) 0.0526(12) Uani 1 1 d . . . . .
C8 C 0.5974(3) 0.4547(3) 0.4786(4) 0.0520(12) Uani 1 1 d . . . . .
C9 C 0.5719(3) 0.3831(3) 0.4239(4) 0.0610(15) Uani 1 1 d . . . . .
C10 C 0.6090(4) 0.2604(3) 0.3548(5) 0.088(2) Uani 1 1 d . . . . .
H10A H 0.581666 0.271165 0.294111 0.132 Uiso 1 1 calc GR . . . .
H10B H 0.574390 0.231034 0.397932 0.132 Uiso 1 1 calc GR . . . .
H10C H 0.656121 0.229596 0.341712 0.132 Uiso 1 1 calc GR . . . .
C11 C 0.5542(3) 0.6235(3) 0.6375(4) 0.0590(14) Uani 1 1 d . . . . .
H11A H 0.563086 0.606625 0.704906 0.071 Uiso 1 1 calc R . . . .
H11B H 0.497133 0.629642 0.627709 0.071 Uiso 1 1 calc R . . . .
C12 C 0.5952(3) 0.7017(3) 0.6197(5) 0.0650(16) Uani 1 1 d . . . . .
H12A H 0.580615 0.739202 0.671022 0.078 Uiso 1 1 calc R . . . .
H12B H 0.577800 0.723564 0.557175 0.078 Uiso 1 1 calc R . . . .
C13 C 0.6850(3) 0.6912(3) 0.6185(4) 0.0493(12) Uani 1 1 d . . . . .
C14 C 0.7352(3) 0.7514(3) 0.6534(4) 0.0526(12) Uani 1 1 d . . . . .
H14 H 0.712895 0.796934 0.681301 0.063 Uiso 1 1 calc R . . . .
C15 C 0.8173(3) 0.7451(3) 0.6474(4) 0.0498(12) Uani 1 1 d . . . . .
C16 C 0.8395(3) 0.8684(3) 0.7326(5) 0.0774(18) Uani 1 1 d . . . . .
H16A H 0.806724 0.899586 0.689205 0.116 Uiso 1 1 calc GR . . . .
H16B H 0.882875 0.900553 0.756286 0.116 Uiso 1 1 calc GR . . . .
H16C H 0.807967 0.850362 0.787304 0.116 Uiso 1 1 calc GR . . . .
C17 C 0.8501(2) 0.6761(3) 0.6053(4) 0.0467(11) Uani 1 1 d . . . . .
C18 C 0.9671(3) 0.6064(3) 0.5550(5) 0.0625(15) Uani 1 1 d . . . . .
H18A H 0.946368 0.599750 0.489670 0.094 Uiso 1 1 calc GR . . . .
H18B H 0.954534 0.560109 0.593677 0.094 Uiso 1 1 calc GR . . . .
H18C H 1.024011 0.612968 0.552021 0.094 Uiso 1 1 calc GR . . . .
C19 C 0.8015(2) 0.6146(3) 0.5753(3) 0.0463(12) Uani 1 1 d . . . . .
H19 H 0.824078 0.567704 0.551532 0.056 Uiso 1 1 calc R . . . .
C20 C 0.7178(2) 0.6219(3) 0.5801(4) 0.0445(11) Uani 1 1 d . . . . .
C21 C 0.7832(3) 0.5120(3) 0.3658(4) 0.0532(13) Uani 1 1 d . . . . .
H21 H 0.760515 0.561350 0.351765 0.064 Uiso 1 1 calc R . . . .
C22 C 0.8501(3) 0.4884(3) 0.3150(4) 0.0580(13) Uani 1 1 d . . . . .
H22 H 0.872959 0.521725 0.268096 0.070 Uiso 1 1 calc R . . . .


_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 C1 1.758(4) . ?
O1 C9 1.319(6) . ?
O1 C10 1.440(6) . ?
O2 C9 1.189(6) . ?
O3 C15 1.365(5) . ?
O3 C16 1.438(6) . ?
O4 C17 1.377(5) . ?
O4 C18 1.421(5) . ?
N1 C6 1.380(5) . ?
N1 C7 1.367(6) . ?
N1 C11 1.451(5) . ?
C1 C2 1.369(7) . ?
C1 C22 1.367(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(6) . ?
C4 C5 1.494(6) . ?
C4 C21 1.376(6) . ?
C5 C6 1.383(6) . ?
C5 C8 1.429(6) . ?
C6 C20 1.465(6) . ?
C7 C7 1.463(8) 2_665 ?
C7 C8 1.380(7) . ?
C8 C9 1.473(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.499(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.513(6) . ?
C13 C14 1.397(6) . ?
C13 C20 1.386(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(6) . ?
C15 C17 1.402(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.375(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.408(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(6) . ?
C22 H22 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
C9 O1 C10 116.2(4) . . ?
C15 O3 C16 117.5(4) . . ?
C17 O4 C18 116.5(3) . . ?
C6 N1 C11 122.9(4) . . ?
C7 N1 C6 109.9(4) . . ?
C7 N1 C11 127.0(4) . . ?
C2 C1 Cl1 118.9(4) . . ?
C22 C1 Cl1 119.6(4) . . ?
C22 C1 C2 121.4(4) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(5) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 122.2(4) . . ?
C21 C4 C3 117.2(4) . . ?
C21 C4 C5 120.5(4) . . ?
C6 C5 C4 126.9(4) . . ?
C6 C5 C8 106.9(4) . . ?
C8 C5 C4 125.9(4) . . ?
N1 C6 C5 107.7(4) . . ?
N1 C6 C20 117.4(4) . . ?
C5 C6 C20 134.8(4) . . ?
N1 C7 C7 122.4(5) . 2_665 ?
N1 C7 C8 107.9(4) . . ?
C8 C7 C7 129.0(5) . 2_665 ?
C5 C8 C9 130.6(4) . . ?
C7 C8 C5 107.6(4) . . ?
C7 C8 C9 121.8(4) . . ?
O1 C9 C8 113.7(4) . . ?
O2 C9 O1 121.3(5) . . ?
O2 C9 C8 124.9(5) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
N1 C11 C12 109.8(4) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 C13 110.8(4) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C14 C13 C12 120.7(4) . . ?
C20 C13 C12 119.7(4) . . ?
C20 C13 C14 119.6(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
O3 C15 C14 125.4(4) . . ?
O3 C15 C17 116.0(4) . . ?
C14 C15 C17 118.5(4) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C15 115.3(4) . . ?
C19 C17 O4 124.3(4) . . ?
C19 C17 C15 120.4(4) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19 119.6 . . ?
C17 C19 C20 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C13 C20 C6 119.3(4) . . ?
C13 C20 C19 118.9(4) . . ?
C19 C20 C6 121.7(4) . . ?
C4 C21 H21 119.0 . . ?
C22 C21 C4 121.9(4) . . ?
C22 C21 H21 119.0 . . ?
C1 C22 C21 118.9(5) . . ?
C1 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -177.1(4) . . . . ?
Cl1 C1 C22 C21 175.9(4) . . . . ?
O3 C15 C17 O4 -2.8(6) . . . . ?
O3 C15 C17 C19 176.1(4) . . . . ?
O4 C17 C19 C20 -177.0(4) . . . . ?
N1 C6 C20 C13 -12.5(7) . . . . ?
N1 C6 C20 C19 167.6(4) . . . . ?
N1 C7 C8 C5 -1.2(6) . . . . ?
N1 C7 C8 C9 -179.0(5) . . . . ?
N1 C11 C12 C13 -50.3(6) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C2 C1 C22 C21 -1.7(8) . . . . ?
C2 C3 C4 C5 176.5(5) . . . . ?
C2 C3 C4 C21 -1.6(8) . . . . ?
C3 C4 C5 C6 120.6(6) . . . . ?
C3 C4 C5 C8 -66.2(7) . . . . ?
C3 C4 C21 C22 0.4(7) . . . . ?
C4 C5 C6 N1 174.2(4) . . . . ?
C4 C5 C6 C20 -3.7(9) . . . . ?
C4 C5 C8 C7 -173.5(5) . . . . ?
C4 C5 C8 C9 4.0(9) . . . . ?
C4 C21 C22 C1 1.2(8) . . . . ?
C5 C4 C21 C22 -177.7(5) . . . . ?
C5 C6 C20 C13 165.2(5) . . . . ?
C5 C6 C20 C19 -14.7(9) . . . . ?
C5 C8 C9 O1 18.7(8) . . . . ?
C5 C8 C9 O2 -163.2(6) . . . . ?
C6 N1 C7 C7 -169.9(4) . . . 2_665 ?
C6 N1 C7 C8 1.2(6) . . . . ?
C6 N1 C11 C12 39.3(6) . . . . ?
C6 C5 C8 C7 0.7(6) . . . . ?
C6 C5 C8 C9 178.3(5) . . . . ?
C7 N1 C6 C5 -0.7(6) . . . . ?
C7 N1 C6 C20 177.6(4) . . . . ?
C7 N1 C11 C12 -146.3(5) . . . . ?
C7 C7 C8 C5 169.1(5) 2_665 . . . ?
C7 C7 C8 C9 -8.7(9) 2_665 . . . ?
C7 C8 C9 O1 -164.1(5) . . . . ?
C7 C8 C9 O2 14.1(9) . . . . ?
C8 C5 C6 N1 0.0(5) . . . . ?
C8 C5 C6 C20 -177.9(5) . . . . ?
C10 O1 C9 O2 -3.4(9) . . . . ?
C10 O1 C9 C8 174.8(5) . . . . ?
C11 N1 C6 C5 174.5(4) . . . . ?
C11 N1 C6 C20 -7.2(7) . . . . ?
C11 N1 C7 C7 15.1(7) . . . 2_665 ?
C11 N1 C7 C8 -173.8(5) . . . . ?
C11 C12 C13 C14 -146.6(5) . . . . ?
C11 C12 C13 C20 35.0(7) . . . . ?
C12 C13 C14 C15 -176.0(5) . . . . ?
C12 C13 C20 C6 -2.8(7) . . . . ?
C12 C13 C20 C19 177.0(5) . . . . ?
C13 C14 C15 O3 -179.3(5) . . . . ?
C13 C14 C15 C17 -0.1(7) . . . . ?
C14 C13 C20 C6 178.8(5) . . . . ?
C14 C13 C20 C19 -1.4(7) . . . . ?
C14 C15 C17 O4 177.9(4) . . . . ?
C14 C15 C17 C19 -3.2(7) . . . . ?
C15 C17 C19 C20 4.2(7) . . . . ?
C16 O3 C15 C14 5.2(7) . . . . ?
C16 O3 C15 C17 -174.0(5) . . . . ?
C17 C19 C20 C6 177.9(5) . . . . ?
C17 C19 C20 C13 -1.9(7) . . . . ?
C18 O4 C17 C15 -179.0(4) . . . . ?
C18 O4 C17 C19 2.2(7) . . . . ?
C20 C13 C14 C15 2.4(8) . . . . ?
C21 C4 C5 C6 -61.3(7) . . . . ?
C21 C4 C5 C8 111.9(5) . . . . ?
C22 C1 C2 C3 0.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.772
