# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20220330
_database_code_depnum_ccdc_archive 'CCDC 2170961'
loop_
_audit_author_name
_audit_author_address
'Dong Li'
; Hubei University of Technology
China
;
_audit_update_record             
;
2022-05-06 deposited with the CCDC.	2022-09-11 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl N O3'
_chemical_formula_sum            'C21 H16 Cl N O3'
_chemical_formula_weight         365.80
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2Br1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   8.9190(3)
_cell_length_b                   24.1190(8)
_cell_length_c                   16.1511(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3474.39(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4270
_cell_measurement_theta_min      5.2830
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    2.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13535
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.142
_diffrn_reflns_theta_min         3.665
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -38.00   1.00    3.00    --  -33.50 178.00 150.00   70
  2  ω     78.00 104.00   1.00    3.00    --   36.47 178.00-180.00   26
  3  ω     11.00  58.00   1.00    3.00    --   36.47 -99.00-180.00   47
  4  ω     11.00  40.00   1.00    3.00    --   36.47 -37.00 120.00   29
  5  ω    -24.00   2.00   1.00    3.00    --   36.47 -37.00 120.00   26
  6  ω     18.00 104.00   1.00    3.00    --   36.47  57.00 120.00   86
  7  ω     49.00 124.00   1.00   12.50    --  108.00 -45.00  90.00   75
  8  ω     92.00 167.00   1.00   12.50    --  108.00  61.00 -90.00   75
  9  ω     40.00 134.00   1.00   12.50    --  108.00 -77.00 -30.00   94
 10  ω     54.00  86.00   1.00   12.50    --  108.00 -94.00-180.00   32
 11  ω    136.00 162.00   1.00   12.50    --  108.00  61.00  30.00   26
 12  ω     62.00 100.00   1.00    3.00    --   36.47 178.00 -60.00   38
 13  ω    -29.00  20.00   1.00    3.00    --   36.47 -77.00 150.00   49
 14  ω     64.00 103.00   1.00    3.00    --   36.47 178.00 150.00   39
 15  ω     52.00  86.00   1.00    3.00    --   36.47  77.00 150.00   34
 16  ω     64.00 147.00   1.00   12.50    --  108.00 178.00   0.00   83
 17  ω     88.00 132.00   1.00   12.50    --  108.00  45.00  60.00   44
 18  ω     47.00  89.00   1.00   12.50    --  108.00 -94.00 -60.00   42
 19  ω    115.00 145.00   1.00   12.50    --  108.00  61.00-150.00   30
;
_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      0.1382361000
_diffrn_orient_matrix_UB_12      0.0364867000
_diffrn_orient_matrix_UB_13      -0.0175061000
_diffrn_orient_matrix_UB_21      0.0874130000
_diffrn_orient_matrix_UB_22      -0.0515232000
_diffrn_orient_matrix_UB_23      -0.0291167000
_diffrn_orient_matrix_UB_31      -0.0555981000
_diffrn_orient_matrix_UB_32      0.0096705000
_diffrn_orient_matrix_UB_33      -0.0891224000
_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         0.531
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.565
_reflns_number_gt                4602
_reflns_number_total             5271
_reflns_odcompleteness_completeness 99.92
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.3380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
 C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20),
 C21(H21), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C18'(H18'),
 C19'(H19'), C20'(H20'), C21'(H21')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.47314(13) 0.47071(4) 0.44946(7) 0.0611(3) Uani 1 1 d . . . . .
O1 O 0.7743(5) 0.22452(13) 0.3813(2) 0.0832(12) Uani 1 1 d . . . . .
O2 O 0.7976(4) 0.40086(13) 0.6827(2) 0.0711(9) Uani 1 1 d . . . . .
O3 O 0.5769(5) 0.57292(13) 0.5169(3) 0.0867(12) Uani 1 1 d . . . . .
N1 N 0.7204(4) 0.28775(12) 0.4828(2) 0.0467(7) Uani 1 1 d . . . . .
C1 C 0.6591(4) 0.24962(15) 0.5408(2) 0.0430(8) Uani 1 1 d . . . . .
C2 C 0.7031(5) 0.25055(18) 0.6227(3) 0.0538(9) Uani 1 1 d . . . . .
H2 H 0.7737 0.2763 0.6405 0.065 Uiso 1 1 calc R . . . .
C3 C 0.6421(6) 0.2132(2) 0.6785(3) 0.0676(12) Uani 1 1 d . . . . .
H3 H 0.6708 0.2142 0.7338 0.081 Uiso 1 1 calc R . . . .
C4 C 0.5391(6) 0.1747(2) 0.6520(3) 0.0721(14) Uani 1 1 d . . . . .
H4 H 0.4990 0.1492 0.6891 0.086 Uiso 1 1 calc R . . . .
C5 C 0.4959(6) 0.1741(2) 0.5706(3) 0.0716(14) Uani 1 1 d . . . . .
H5 H 0.4275 0.1476 0.5526 0.086 Uiso 1 1 calc R . . . .
C6 C 0.5521(5) 0.21198(18) 0.5149(3) 0.0537(9) Uani 1 1 d . . . . .
H6 H 0.5184 0.2123 0.4604 0.064 Uiso 1 1 calc R . . . .
C7 C 0.7762(5) 0.27155(17) 0.4077(3) 0.0549(10) Uani 1 1 d . . . . .
C8 C 0.8410(6) 0.32247(18) 0.3661(3) 0.0659(12) Uani 1 1 d . . . . .
H8A H 0.9494 0.3200 0.3633 0.079 Uiso 1 1 calc R . . . .
H8B H 0.8019 0.3263 0.3104 0.079 Uiso 1 1 calc R . . . .
C9 C 0.7938(5) 0.37102(17) 0.4192(3) 0.0582(10) Uani 1 1 d . . . . .
H9A H 0.7072 0.3895 0.3955 0.070 Uiso 1 1 calc R . . . .
H9B H 0.8748 0.3976 0.4244 0.070 Uiso 1 1 calc R . . . .
C10 C 0.7549(5) 0.34570(16) 0.5037(3) 0.0497(9) Uani 1 1 d . . . . .
H10 H 0.8431 0.3470 0.5399 0.060 Uiso 1 1 calc R . . . .
C11 C 0.6226(5) 0.37312(16) 0.5469(3) 0.0510(9) Uani 1 1 d . . . . .
H11A H 0.5360 0.3718 0.5105 0.061 Uiso 1 1 calc R . . . .
H11B H 0.5983 0.3523 0.5965 0.061 Uiso 1 1 calc R . . . .
C12 C 0.7528(5) 0.44062(16) 0.6442(3) 0.0498(9) Uani 1 1 d . . . . .
C13 C 0.6532(4) 0.43224(15) 0.5700(2) 0.0451(8) Uani 1 1 d . . . . .
C14 C 0.5972(4) 0.47635(16) 0.5317(3) 0.0479(8) Uani 1 1 d . . . . .
C15 C 0.6304(5) 0.53483(16) 0.5552(3) 0.0529(9) Uani 1 1 d . . . . .
C16 C 0.7311(4) 0.54351(16) 0.6265(3) 0.0497(9) Uani 1 1 d . . . . .
C17 C 0.7909(4) 0.49821(17) 0.6697(2) 0.0505(9) Uani 1 1 d . . . . .
C18 C 0.8837(6) 0.5071(2) 0.7365(3) 0.0677(12) Uani 1 1 d . . . . .
H18 H 0.9229 0.4772 0.7657 0.081 Uiso 1 1 calc R . . . .
C19 C 0.9189(7) 0.5615(2) 0.7603(4) 0.0801(15) Uani 1 1 d . . . . .
H19 H 0.9809 0.5676 0.8056 0.096 Uiso 1 1 calc R . . . .
C20 C 0.8624(6) 0.6054(2) 0.7169(3) 0.0719(14) Uani 1 1 d . . . . .
H20 H 0.8880 0.6413 0.7325 0.086 Uiso 1 1 calc R . . . .
C21 C 0.7683(5) 0.59722(18) 0.6507(3) 0.0626(11) Uani 1 1 d . . . . .
H21 H 0.7296 0.6274 0.6220 0.075 Uiso 1 1 calc R . . . .
Cl1' Cl 0.68951(14) 0.03390(6) 0.18551(8) 0.0739(3) Uani 1 1 d . . . . .
O1' O 0.4085(5) 0.27355(14) 0.0915(2) 0.0758(10) Uani 1 1 d . . . . .
O2' O 0.3408(4) 0.10819(12) 0.4044(2) 0.0654(8) Uani 1 1 d . . . . .
O3' O 0.5983(4) -0.06663(14) 0.2637(2) 0.0735(10) Uani 1 1 d . . . . .
N1' N 0.3878(4) 0.21155(13) 0.1987(2) 0.0521(8) Uani 1 1 d . . . . .
C1' C 0.3603(5) 0.24973(17) 0.2644(3) 0.0509(9) Uani 1 1 d . . . . .
C2' C 0.2610(6) 0.2364(2) 0.3261(3) 0.0691(12) Uani 1 1 d . . . . .
H2' H 0.2108 0.2026 0.3252 0.083 Uiso 1 1 calc R . . . .
C3' C 0.2358(7) 0.2741(2) 0.3906(3) 0.0780(15) Uani 1 1 d . . . . .
H3' H 0.1688 0.2651 0.4326 0.094 Uiso 1 1 calc R . . . .
C4' C 0.3089(6) 0.3243(3) 0.3924(3) 0.0779(15) Uani 1 1 d . . . . .
H4' H 0.2909 0.3496 0.4348 0.093 Uiso 1 1 calc R . . . .
C5' C 0.4078(6) 0.3362(2) 0.3312(4) 0.0758(14) Uani 1 1 d . . . . .
H5' H 0.4578 0.3701 0.3321 0.091 Uiso 1 1 calc R . . . .
C6' C 0.4362(5) 0.29970(19) 0.2679(3) 0.0605(11) Uani 1 1 d . . . . .
H6' H 0.5063 0.3086 0.2274 0.073 Uiso 1 1 calc R . . . .
C7' C 0.4075(5) 0.22632(19) 0.1181(3) 0.0577(10) Uani 1 1 d . . . . .
C8' C 0.4303(7) 0.1743(2) 0.0690(3) 0.0811(15) Uani 1 1 d . . . . .
H8'A H 0.5340 0.1710 0.0516 0.097 Uiso 1 1 calc R . . . .
H8'B H 0.3669 0.1743 0.0202 0.097 Uiso 1 1 calc R . . . .
C9' C 0.3883(7) 0.1272(2) 0.1261(3) 0.0811(17) Uani 1 1 d . . . . .
H9'A H 0.4613 0.0974 0.1223 0.097 Uiso 1 1 calc R . . . .
H9'B H 0.2904 0.1125 0.1117 0.097 Uiso 1 1 calc R . . . .
C10' C 0.3863(5) 0.15126(16) 0.2127(3) 0.0561(10) Uani 1 1 d . . . . .
H10' H 0.2920 0.1410 0.2399 0.067 Uiso 1 1 calc R . . . .
C11' C 0.5185(5) 0.13347(16) 0.2682(3) 0.0499(9) Uani 1 1 d . . . . .
H11C H 0.6113 0.1360 0.2372 0.060 Uiso 1 1 calc R . . . .
H11D H 0.5257 0.1583 0.3153 0.060 Uiso 1 1 calc R . . . .
C12' C 0.3926(4) 0.06815(15) 0.3700(2) 0.0459(8) Uani 1 1 d . . . . .
C13' C 0.4971(4) 0.07504(15) 0.2983(2) 0.0445(8) Uani 1 1 d . . . . .
C14' C 0.5622(4) 0.02993(16) 0.2660(2) 0.0480(9) Uani 1 1 d . . . . .
C15' C 0.5325(4) -0.02805(16) 0.2946(3) 0.0510(10) Uani 1 1 d . . . . .
C16' C 0.4212(4) -0.03507(15) 0.3611(3) 0.0496(9) Uani 1 1 d . . . . .
C17' C 0.3547(4) 0.01103(16) 0.3980(2) 0.0455(8) Uani 1 1 d . . . . .
C18' C 0.2502(5) 0.00381(18) 0.4611(3) 0.0559(10) Uani 1 1 d . . . . .
H18' H 0.2070 0.0345 0.4866 0.067 Uiso 1 1 calc R . . . .
C19' C 0.2106(6) -0.0497(2) 0.4859(3) 0.0692(13) Uani 1 1 d . . . . .
H19' H 0.1401 -0.0549 0.5276 0.083 Uiso 1 1 calc R . . . .
C20' C 0.2776(6) -0.09522(19) 0.4477(4) 0.0693(13) Uani 1 1 d . . . . .
H20' H 0.2505 -0.1309 0.4638 0.083 Uiso 1 1 calc R . . . .
C21' C 0.3815(5) -0.08839(18) 0.3877(3) 0.0638(12) Uani 1 1 d . . . . .
H21' H 0.4268 -0.1192 0.3638 0.077 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 C14 1.734(4) . ?
O1 C7 1.212(5) . ?
O2 C12 1.211(5) . ?
O3 C15 1.206(5) . ?
N1 C1 1.422(5) . ?
N1 C7 1.369(5) . ?
N1 C10 1.471(5) . ?
C1 C2 1.380(6) . ?
C1 C6 1.383(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.514(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.535(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.522(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C13 1.499(5) . ?
C12 C13 1.505(5) . ?
C12 C17 1.488(5) . ?
C13 C14 1.328(5) . ?
C14 C15 1.490(5) . ?
C15 C16 1.476(6) . ?
C16 C17 1.401(6) . ?
C16 C21 1.393(5) . ?
C17 C18 1.377(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.402(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(7) . ?
C21 H21 0.9300 . ?
Cl1' C14' 1.729(4) . ?
O1' C7' 1.218(5) . ?
O2' C12' 1.206(5) . ?
O3' C15' 1.208(5) . ?
N1' C1' 1.426(5) . ?
N1' C7' 1.360(6) . ?
N1' C10' 1.472(5) . ?
C1' C2' 1.373(7) . ?
C1' C6' 1.383(6) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.400(7) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.377(8) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.356(8) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.374(7) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.500(7) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C9' 1.512(8) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C10' 1.515(7) . ?
C10' H10' 0.9800 . ?
C10' C11' 1.542(5) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C11' C13' 1.503(5) . ?
C12' C13' 1.496(6) . ?
C12' C17' 1.489(5) . ?
C13' C14' 1.339(5) . ?
C14' C15' 1.496(6) . ?
C15' C16' 1.472(6) . ?
C16' C17' 1.394(5) . ?
C16' C21' 1.401(6) . ?
C17' C18' 1.392(6) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.396(6) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.394(8) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.351(8) . ?
C21' H21' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C10 123.0(3) . . ?
C7 N1 C1 122.6(3) . . ?
C7 N1 C10 113.5(3) . . ?
C2 C1 N1 120.8(4) . . ?
C2 C1 C6 119.8(4) . . ?
C6 C1 N1 119.4(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 H6 120.4 . . ?
O1 C7 N1 125.0(4) . . ?
O1 C7 C8 127.5(4) . . ?
N1 C7 C8 107.5(4) . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 105.7(4) . . ?
C9 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C8 C9 C10 105.0(3) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N1 C10 C9 102.8(3) . . ?
N1 C10 H10 109.6 . . ?
N1 C10 C11 110.8(3) . . ?
C9 C10 H10 109.6 . . ?
C11 C10 C9 114.2(4) . . ?
C11 C10 H10 109.6 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C11 C10 112.7(3) . . ?
C13 C11 H11A 109.1 . . ?
C13 C11 H11B 109.1 . . ?
O2 C12 C13 119.8(4) . . ?
O2 C12 C17 121.5(4) . . ?
C17 C12 C13 118.7(3) . . ?
C11 C13 C12 115.7(3) . . ?
C14 C13 C11 125.3(4) . . ?
C14 C13 C12 119.0(4) . . ?
C13 C14 Cl1 122.3(3) . . ?
C13 C14 C15 124.4(4) . . ?
C15 C14 Cl1 113.3(3) . . ?
O3 C15 C14 120.8(4) . . ?
O3 C15 C16 122.2(4) . . ?
C16 C15 C14 117.0(4) . . ?
C17 C16 C15 120.6(4) . . ?
C21 C16 C15 119.7(4) . . ?
C21 C16 C17 119.7(4) . . ?
C16 C17 C12 120.2(4) . . ?
C18 C17 C12 119.9(4) . . ?
C18 C17 C16 119.8(4) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.8(5) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.8(5) . . ?
C20 C21 H21 120.1 . . ?
C1' N1' C10' 121.5(4) . . ?
C7' N1' C1' 124.4(4) . . ?
C7' N1' C10' 114.0(4) . . ?
C2' C1' N1' 120.0(4) . . ?
C2' C1' C6' 119.3(4) . . ?
C6' C1' N1' 120.6(4) . . ?
C1' C2' H2' 120.3 . . ?
C1' C2' C3' 119.5(5) . . ?
C3' C2' H2' 120.3 . . ?
C2' C3' H3' 119.6 . . ?
C4' C3' C2' 120.8(5) . . ?
C4' C3' H3' 119.6 . . ?
C3' C4' H4' 120.7 . . ?
C5' C4' C3' 118.6(5) . . ?
C5' C4' H4' 120.7 . . ?
C4' C5' H5' 119.1 . . ?
C4' C5' C6' 121.8(5) . . ?
C6' C5' H5' 119.1 . . ?
C1' C6' H6' 120.0 . . ?
C5' C6' C1' 120.0(5) . . ?
C5' C6' H6' 120.0 . . ?
O1' C7' N1' 125.7(4) . . ?
O1' C7' C8' 126.5(5) . . ?
N1' C7' C8' 107.8(4) . . ?
C7' C8' H8'A 110.6 . . ?
C7' C8' H8'B 110.6 . . ?
C7' C8' C9' 105.8(4) . . ?
H8'A C8' H8'B 108.7 . . ?
C9' C8' H8'A 110.6 . . ?
C9' C8' H8'B 110.6 . . ?
C8' C9' H9'A 110.5 . . ?
C8' C9' H9'B 110.5 . . ?
C8' C9' C10' 106.2(4) . . ?
H9'A C9' H9'B 108.7 . . ?
C10' C9' H9'A 110.5 . . ?
C10' C9' H9'B 110.5 . . ?
N1' C10' C9' 103.7(4) . . ?
N1' C10' H10' 109.0 . . ?
N1' C10' C11' 110.9(3) . . ?
C9' C10' H10' 109.0 . . ?
C9' C10' C11' 114.9(4) . . ?
C11' C10' H10' 109.0 . . ?
C10' C11' H11C 109.5 . . ?
C10' C11' H11D 109.5 . . ?
H11C C11' H11D 108.1 . . ?
C13' C11' C10' 110.6(3) . . ?
C13' C11' H11C 109.5 . . ?
C13' C11' H11D 109.5 . . ?
O2' C12' C13' 120.4(4) . . ?
O2' C12' C17' 120.9(4) . . ?
C17' C12' C13' 118.7(3) . . ?
C12' C13' C11' 115.7(3) . . ?
C14' C13' C11' 125.6(4) . . ?
C14' C13' C12' 118.8(4) . . ?
C13' C14' Cl1' 122.2(3) . . ?
C13' C14' C15' 124.2(4) . . ?
C15' C14' Cl1' 113.6(3) . . ?
O3' C15' C14' 120.4(4) . . ?
O3' C15' C16' 122.7(4) . . ?
C16' C15' C14' 116.9(3) . . ?
C17' C16' C15' 120.5(4) . . ?
C17' C16' C21' 119.5(4) . . ?
C21' C16' C15' 120.0(4) . . ?
C16' C17' C12' 120.7(4) . . ?
C18' C17' C12' 119.4(4) . . ?
C18' C17' C16' 119.9(4) . . ?
C17' C18' H18' 120.2 . . ?
C17' C18' C19' 119.7(4) . . ?
C19' C18' H18' 120.2 . . ?
C18' C19' H19' 120.2 . . ?
C20' C19' C18' 119.5(5) . . ?
C20' C19' H19' 120.2 . . ?
C19' C20' H20' 119.5 . . ?
C21' C20' C19' 121.0(4) . . ?
C21' C20' H20' 119.5 . . ?
C16' C21' H21' 119.8 . . ?
C20' C21' C16' 120.4(5) . . ?
C20' C21' H21' 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C14 C15 O3 -2.2(6) . . . . ?
Cl1 C14 C15 C16 178.0(3) . . . . ?
O1 C7 C8 C9 171.9(5) . . . . ?
O2 C12 C13 C11 -2.8(6) . . . . ?
O2 C12 C13 C14 175.7(4) . . . . ?
O2 C12 C17 C16 -176.7(4) . . . . ?
O2 C12 C17 C18 2.5(7) . . . . ?
O3 C15 C16 C17 179.8(5) . . . . ?
O3 C15 C16 C21 -0.8(7) . . . . ?
N1 C1 C2 C3 179.9(4) . . . . ?
N1 C1 C6 C5 178.2(4) . . . . ?
N1 C7 C8 C9 -9.0(5) . . . . ?
N1 C10 C11 C13 179.6(3) . . . . ?
C1 N1 C7 O1 3.1(7) . . . . ?
C1 N1 C7 C8 -176.0(4) . . . . ?
C1 N1 C10 C9 -171.6(3) . . . . ?
C1 N1 C10 C11 -49.3(5) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C1 C6 C5 -3.1(6) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C4 C5 C6 C1 3.0(8) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
C7 N1 C1 C2 131.1(4) . . . . ?
C7 N1 C1 C6 -50.2(5) . . . . ?
C7 N1 C10 C9 19.1(5) . . . . ?
C7 N1 C10 C11 141.4(4) . . . . ?
C7 C8 C9 C10 20.1(5) . . . . ?
C8 C9 C10 N1 -23.2(4) . . . . ?
C8 C9 C10 C11 -143.3(4) . . . . ?
C9 C10 C11 C13 -65.0(5) . . . . ?
C10 N1 C1 C2 -37.2(5) . . . . ?
C10 N1 C1 C6 141.4(4) . . . . ?
C10 N1 C7 O1 172.4(5) . . . . ?
C10 N1 C7 C8 -6.7(5) . . . . ?
C10 C11 C13 C12 -75.9(5) . . . . ?
C10 C11 C13 C14 105.7(5) . . . . ?
C11 C13 C14 Cl1 2.0(6) . . . . ?
C11 C13 C14 C15 -179.3(4) . . . . ?
C12 C13 C14 Cl1 -176.3(3) . . . . ?
C12 C13 C14 C15 2.4(6) . . . . ?
C12 C17 C18 C19 -179.9(5) . . . . ?
C13 C12 C17 C16 1.8(6) . . . . ?
C13 C12 C17 C18 -179.0(4) . . . . ?
C13 C14 C15 O3 179.0(5) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C21 179.0(4) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C15 C16 C17 C18 -179.5(4) . . . . ?
C15 C16 C21 C20 -179.8(4) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C12 C13 C11 178.7(3) . . . . ?
C17 C12 C13 C14 -2.8(6) . . . . ?
C17 C16 C21 C20 -0.4(7) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
C18 C19 C20 C21 1.3(9) . . . . ?
C19 C20 C21 C16 -0.8(8) . . . . ?
C21 C16 C17 C12 -179.6(4) . . . . ?
C21 C16 C17 C18 1.1(6) . . . . ?
Cl1' C14' C15' O3' 2.2(5) . . . . ?
Cl1' C14' C15' C16' -177.9(3) . . . . ?
O1' C7' C8' C9' -169.0(5) . . . . ?
O2' C12' C13' C11' -5.9(5) . . . . ?
O2' C12' C13' C14' 174.5(4) . . . . ?
O2' C12' C17' C16' -176.5(4) . . . . ?
O2' C12' C17' C18' 4.4(5) . . . . ?
O3' C15' C16' C17' 176.2(4) . . . . ?
O3' C15' C16' C21' -3.8(6) . . . . ?
N1' C1' C2' C3' 179.5(4) . . . . ?
N1' C1' C6' C5' 179.6(4) . . . . ?
N1' C7' C8' C9' 12.1(6) . . . . ?
N1' C10' C11' C13' 167.0(4) . . . . ?
C1' N1' C7' O1' 2.1(8) . . . . ?
C1' N1' C7' C8' -178.9(4) . . . . ?
C1' N1' C10' C9' 168.8(4) . . . . ?
C1' N1' C10' C11' -67.3(5) . . . . ?
C1' C2' C3' C4' 0.3(8) . . . . ?
C2' C1' C6' C5' -2.3(7) . . . . ?
C2' C3' C4' C5' -1.0(8) . . . . ?
C3' C4' C5' C6' 0.1(8) . . . . ?
C4' C5' C6' C1' 1.5(8) . . . . ?
C6' C1' C2' C3' 1.4(7) . . . . ?
C7' N1' C1' C2' 141.3(5) . . . . ?
C7' N1' C1' C6' -40.6(6) . . . . ?
C7' N1' C10' C9' -7.1(5) . . . . ?
C7' N1' C10' C11' 116.8(4) . . . . ?
C7' C8' C9' C10' -16.1(6) . . . . ?
C8' C9' C10' N1' 14.1(5) . . . . ?
C8' C9' C10' C11' -107.2(5) . . . . ?
C9' C10' C11' C13' -75.8(5) . . . . ?
C10' N1' C1' C2' -34.2(6) . . . . ?
C10' N1' C1' C6' 143.9(4) . . . . ?
C10' N1' C7' O1' 177.9(5) . . . . ?
C10' N1' C7' C8' -3.1(5) . . . . ?
C10' C11' C13' C12' -79.9(4) . . . . ?
C10' C11' C13' C14' 99.6(5) . . . . ?
C11' C13' C14' Cl1' 2.8(5) . . . . ?
C11' C13' C14' C15' -176.7(3) . . . . ?
C12' C13' C14' Cl1' -177.7(3) . . . . ?
C12' C13' C14' C15' 2.8(5) . . . . ?
C12' C17' C18' C19' 178.0(4) . . . . ?
C13' C12' C17' C16' 3.3(5) . . . . ?
C13' C12' C17' C18' -175.9(3) . . . . ?
C13' C14' C15' O3' -178.2(4) . . . . ?
C13' C14' C15' C16' 1.6(5) . . . . ?
C14' C15' C16' C17' -3.6(5) . . . . ?
C14' C15' C16' C21' 176.4(3) . . . . ?
C15' C16' C17' C12' 1.2(5) . . . . ?
C15' C16' C17' C18' -179.7(3) . . . . ?
C15' C16' C21' C20' -178.9(4) . . . . ?
C16' C17' C18' C19' -1.2(6) . . . . ?
C17' C12' C13' C11' 174.3(3) . . . . ?
C17' C12' C13' C14' -5.2(5) . . . . ?
C17' C16' C21' C20' 1.1(6) . . . . ?
C17' C18' C19' C20' 0.7(6) . . . . ?
C18' C19' C20' C21' 0.7(7) . . . . ?
C19' C20' C21' C16' -1.6(7) . . . . ?
C21' C16' C17' C12' -178.9(3) . . . . ?
C21' C16' C17' C18' 0.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.918
