# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_2719_autored
_database_code_depnum_ccdc_archive 'CCDC 2235158'
loop_
_audit_author_name
_audit_author_address
indole
;zhe jiang normal university
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Cl N O2'
_chemical_formula_sum            'C24 H20 Cl N O2'
_chemical_formula_weight         389.86
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8922(2)
_cell_length_b                   10.1765(3)
_cell_length_c                   14.9016(4)
_cell_angle_alpha                109.628(2)
_cell_angle_beta                 97.057(2)
_cell_angle_gamma                93.235(2)
_cell_volume                     971.63(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13568
_cell_measurement_temperature    190(20)
_cell_measurement_theta_max      74.1040
_cell_measurement_theta_min      3.1740
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.583
_exptl_absorpt_coefficient_mu    1.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (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    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19351
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  11.00   1.00    1.00    --    0.00  37.00  60.00   26
  2  ω    -30.00  52.00   1.00    1.00    --    0.00  77.00 150.00   82
  3  ω    -87.00 -58.00   1.00    1.00    --    0.00 -57.00 -60.00   29
  4  ω    -42.00  16.00   1.00    1.00    --    0.00 -37.00 120.00   58
  5  ω    -70.00 -40.00   1.00    1.00    --    0.00 -37.00  30.00   30
  6  ω     38.00  72.00   1.00    1.00    --    0.00  37.00  60.00   34
  7  ω     51.00  87.00   1.00    1.00    --    0.00  57.00 -90.00   36
  8  ω    -23.00  23.00   1.00    1.00    --    0.00 -57.00 -60.00   46
  9  ω     57.00  85.00   1.00    1.00    --    0.00  77.00 150.00   28
 10  ω    -29.00  28.00   1.00    1.00    --    0.00  77.00 -60.00   57
 11  ω     51.00  88.00   1.00    1.00    --    0.00  77.00 -60.00   37
 12  ω     -2.00  25.00   1.00    1.00    --    0.00  57.00 -90.00   27
 13  ω    -27.00  19.00   1.00    1.00    --    0.00 -37.00  30.00   46
 14  ω     71.00 131.00   1.00    2.00    --   95.80  61.00 -30.00   60
 15  ω    125.00 184.00   1.00    2.00    --   95.80  61.00-150.00   59
 16  ω      7.00 128.00   1.00    2.00    --   95.80 -82.00 -30.00  121
 17  ω     71.00  99.00   1.00    2.00    --   95.80  61.00-150.00   28
 18  ω     75.00 109.00   1.00    2.00    --   95.80  45.00 -60.00   34
 19  ω     36.00  93.00   1.00    2.00    --   95.80 -61.00 120.00   57
 20  ω    158.00 184.00   1.00    2.00    --   95.80  69.00  61.52   26
 21  ω     63.00  89.00   1.00    2.00    --   95.80  82.00  60.00   26
 22  ω    105.00 131.00   1.00    2.00    --   95.80  77.00-150.00   26
 23  ω    107.00 133.00   1.00    2.00    --   95.80  82.00  60.00   26
 24  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -30.00   26
 25  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
 26  ω     63.00  89.00   1.00    2.00    --   95.80  82.00  30.00   26
 27  ω     65.00  93.00   1.00    2.00    --   95.80  77.00 150.00   28
 28  ω     63.00  88.00   1.00    2.00    --   95.80  82.00   0.00   25
 29  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 30  ω      6.00 125.00   1.00    2.00    --   95.80 -82.00-150.00  119
 31  ω    150.00 181.00   1.00    2.00    --   95.80  77.00 120.00   31
 32  ω     65.00 102.00   1.00    2.00    --   95.80  77.00-150.00   37
 33  ω    155.00 181.00   1.00    2.00    --   95.80  77.00-180.00   26
 34  ω     65.00  98.00   1.00    2.00    --   95.80  77.00 120.00   33
 35  ω      6.00  32.00   1.00    2.00    --   95.80 -61.00 120.00   26
 36  ω     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 37  ω    120.00 185.00   1.00    2.00    --   95.80  45.00 150.00   65
 38  ω     76.00 113.00   1.00    2.00    --   95.80  45.00 150.00   37
 39  ω     65.00  91.00   1.00    2.00    --   95.80  82.00-180.00   26
 40  ω    132.00 157.00   1.00    2.00    --   95.80  82.00-180.00   25
 41  ω     74.00 100.00   1.00    2.00    --   95.80  61.00 -60.00   26
 42  ω     65.00  91.00   1.00    2.00    --   95.80  82.00-120.00   26
 43  ω     75.00 107.00   1.00    2.00    --   95.80  45.00 -90.00   32
 44  ω    117.00 145.00   1.00    2.00    --   95.80  45.00 -90.00   28
 45  ω     74.00 153.00   1.00    2.00    --   95.80  61.00  90.00   79
 46  ω    160.00 185.00   1.00    2.00    --   95.80  61.00  90.00   25
 47  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 48  ω     75.00 159.00   1.00    2.00    --   95.80  45.00-180.00   84
 49  ω     79.00 151.00   1.00    2.00    --   95.80  45.00 -30.00   72
 50  ω     65.00  91.00   1.00    2.00    --   95.80  77.00  90.00   26
 51  ω     66.00  92.00   1.00    2.00    --   95.80  82.00 120.00   26
 52  ω     63.00  88.00   1.00    2.00    --   95.80  82.00 150.00   25
 53  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-150.00   26
 54  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-120.00   25
 55  ω     73.00  98.00   1.00    2.00    --   95.80  61.00 120.00   25
 56  ω     87.00 126.00   1.00    2.00    --   95.80 -82.00  30.00   39
 57  ω     15.00 102.00   1.00    2.00    --   95.80 -61.00-150.00   87
 58  ω     63.00  88.00   1.00    2.00    --   95.80  82.00 -30.00   25
 59  ω     40.00  77.00   1.00    2.00    --   95.80 -82.00  30.00   37
 60  ω     13.00 100.00   1.00    2.00    --   95.80 -82.00 120.00   87
 61  ω     70.00 117.00   1.00    2.00    --   95.80  67.00  28.17   47
 62  ω     71.00 147.00   1.00    2.00    --   95.80  61.00   0.00   76
 63  ω     68.00 135.00   1.00    2.00    --   95.80  69.00  61.52   67
 64  ω     76.00 184.00   1.00    2.00    --   95.80  33.00  62.75  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0418671000
_diffrn_orient_matrix_UB_12      0.0596874000
_diffrn_orient_matrix_UB_13      0.1109327000
_diffrn_orient_matrix_UB_21      0.2198620000
_diffrn_orient_matrix_UB_22      -0.0174312000
_diffrn_orient_matrix_UB_23      -0.0033810000
_diffrn_orient_matrix_UB_31      0.0345823000
_diffrn_orient_matrix_UB_32      0.1491666000
_diffrn_orient_matrix_UB_33      -0.0031629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3275
_reflns_number_total             3432
_reflns_odcompleteness_completeness 99.71
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.072
_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)+(0.0419P)²+0.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0920
_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C24(H24), C18(H18), C3(H3), C23(H23), C12(H12), C21(H21), C6(H6),
 C19(H19), C10(H10), C20(H20), C9(H9), C11(H11), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.96352(6) 0.13596(4) 0.66777(3) 0.03990(14) Uani 1 1 d . . . . .
O1 O 0.68096(14) 0.58884(11) 0.91733(7) 0.0278(2) Uani 1 1 d . . . . .
O2 O 0.42822(15) 0.45583(12) 0.81189(8) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.78664(16) 0.29788(12) 0.83662(8) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.96031(19) 0.58567(15) 0.74257(10) 0.0244(3) Uani 1 1 d . . . . .
C15 C 0.95973(19) 0.49154(15) 0.80200(10) 0.0240(3) Uani 1 1 d . . . . .
H15A H 0.991197 0.550359 0.871019 0.029 Uiso 1 1 calc R U . . .
H15B H 1.065062 0.428984 0.786542 0.029 Uiso 1 1 calc R U . . .
C2 C 0.69308(19) 0.32732(15) 0.67750(10) 0.0228(3) Uani 1 1 d . . . . .
C13 C 0.60160(19) 0.48496(15) 0.83645(10) 0.0227(3) Uani 1 1 d . . . . .
C17 C 0.6525(2) 0.18470(14) 0.82691(10) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.76206(19) 0.40001(14) 0.78602(9) 0.0208(3) Uani 1 1 d . . . . .
C22 C 0.7289(2) 0.12053(15) 0.89259(10) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.8688(2) 0.70916(16) 0.76573(11) 0.0295(3) Uani 1 1 d . . . . .
H8 H 0.804002 0.735808 0.820886 0.035 Uiso 1 1 calc R U . . .
C24 C 0.9416(2) 0.30416(16) 0.90740(11) 0.0290(3) Uani 1 1 d . . . . .
H24 H 1.052650 0.372534 0.928381 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4712(2) 0.13529(16) 0.76805(11) 0.0281(3) Uani 1 1 d . . . . .
H18 H 0.420115 0.179070 0.724359 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5552(2) 0.38480(17) 0.62858(11) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.505515 0.469125 0.663627 0.035 Uiso 1 1 calc R U . . .
C23 C 0.9119(2) 0.19906(17) 0.94222(11) 0.0320(3) Uani 1 1 d . . . . .
H23 H 0.997282 0.180848 0.990809 0.038 Uiso 1 1 calc R U . . .
C12 C 1.0566(2) 0.55114(17) 0.66260(11) 0.0327(3) Uani 1 1 d . . . . .
H12 H 1.120436 0.467757 0.645618 0.039 Uiso 1 1 calc R U . . .
C21 C 0.6202(2) 0.00405(16) 0.89891(11) 0.0324(3) Uani 1 1 d . . . . .
H21 H 0.668946 -0.040062 0.942810 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5412(2) 0.66889(17) 0.97267(12) 0.0338(4) Uani 1 1 d . . . . .
H14A H 0.462595 0.712709 0.933373 0.051 Uiso 1 1 calc R U . . .
H14B H 0.612257 0.741822 1.030607 0.051 Uiso 1 1 calc R U . . .
H14C H 0.454462 0.606228 0.991440 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7008(3) 0.14400(18) 0.52279(12) 0.0372(4) Uani 1 1 d . . . . .
H6 H 0.751825 0.060965 0.486607 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3690(2) 0.01963(17) 0.77610(12) 0.0350(4) Uani 1 1 d . . . . .
H19 H 0.245457 -0.016775 0.736667 0.042 Uiso 1 1 calc R U . . .
C10 C 0.9671(2) 0.75700(17) 0.63012(12) 0.0352(4) Uani 1 1 d . . . . .
H10 H 0.968663 0.814527 0.591437 0.042 Uiso 1 1 calc R U . . .
C20 C 0.4422(2) -0.04524(17) 0.84063(12) 0.0362(4) Uani 1 1 d . . . . .
H20 H 0.367880 -0.124379 0.844150 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8707(2) 0.79353(17) 0.70966(12) 0.0341(4) Uani 1 1 d . . . . .
H9 H 0.805858 0.876455 0.725873 0.041 Uiso 1 1 calc R U . . .
C1 C 0.7704(2) 0.20853(16) 0.62094(11) 0.0283(3) Uani 1 1 d . . . . .
C11 C 1.0614(3) 0.63600(18) 0.60715(12) 0.0379(4) Uani 1 1 d . . . . .
H11 H 1.129633 0.611218 0.553132 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4887(2) 0.32293(19) 0.53076(12) 0.0375(4) Uani 1 1 d . . . . .
H4 H 0.395091 0.364863 0.499752 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5585(3) 0.2004(2) 0.47843(12) 0.0414(4) Uani 1 1 d . . . . .
H5 H 0.508490 0.155245 0.412014 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7414(16) . ?
O1 C13 1.3365(17) . ?
O1 C14 1.4503(17) . ?
O2 C13 1.1956(17) . ?
N1 C17 1.3918(18) . ?
N1 C16 1.4807(17) . ?
N1 C24 1.3883(18) . ?
C7 C15 1.507(2) . ?
C7 C8 1.396(2) . ?
C7 C12 1.387(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5519(18) . ?
C2 C16 1.5350(18) . ?
C2 C3 1.398(2) . ?
C2 C1 1.398(2) . ?
C13 C16 1.5527(18) . ?
C17 C22 1.415(2) . ?
C17 C18 1.395(2) . ?
C22 C23 1.427(2) . ?
C22 C21 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.352(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C23 H23 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.383(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.374(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C1 1.395(2) . ?
C6 C5 1.374(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.400(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.382(2) . ?
C10 C11 1.385(3) . ?
C20 H20 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 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
C13 O1 C14 115.20(11) . . ?
C17 N1 C16 126.23(11) . . ?
C24 N1 C17 107.82(12) . . ?
C24 N1 C16 125.81(12) . . ?
C8 C7 C15 122.28(13) . . ?
C12 C7 C15 119.75(13) . . ?
C12 C7 C8 117.97(14) . . ?
C7 C15 H15A 108.7 . . ?
C7 C15 H15B 108.7 . . ?
C7 C15 C16 114.27(11) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C3 C2 C16 120.18(12) . . ?
C1 C2 C16 123.49(12) . . ?
C1 C2 C3 116.19(13) . . ?
O1 C13 C16 111.20(11) . . ?
O2 C13 O1 123.25(13) . . ?
O2 C13 C16 125.27(13) . . ?
N1 C17 C22 107.45(12) . . ?
N1 C17 C18 130.77(13) . . ?
C18 C17 C22 121.76(13) . . ?
N1 C16 C15 109.60(10) . . ?
N1 C16 C2 112.00(11) . . ?
N1 C16 C13 101.60(10) . . ?
C15 C16 C13 112.67(11) . . ?
C2 C16 C15 109.37(11) . . ?
C2 C16 C13 111.44(11) . . ?
C17 C22 C23 106.96(13) . . ?
C21 C22 C17 119.37(14) . . ?
C21 C22 C23 133.65(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.14(14) . . ?
C9 C8 H8 119.4 . . ?
N1 C24 H24 124.8 . . ?
C23 C24 N1 110.31(13) . . ?
C23 C24 H24 124.8 . . ?
C17 C18 H18 121.5 . . ?
C19 C18 C17 117.08(14) . . ?
C19 C18 H18 121.5 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.20(15) . . ?
C4 C3 H3 118.9 . . ?
C22 C23 H23 126.3 . . ?
C24 C23 C22 107.46(13) . . ?
C24 C23 H23 126.3 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.13(15) . . ?
C11 C12 H12 119.4 . . ?
C22 C21 H21 120.5 . . ?
C20 C21 C22 118.95(15) . . ?
C20 C21 H21 120.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C1 120.07(15) . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 121.96(15) . . ?
C20 C19 H19 119.0 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.58(15) . . ?
C11 C10 H10 120.2 . . ?
C21 C20 C19 120.87(15) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.96(15) . . ?
C10 C9 H9 120.0 . . ?
C2 C1 Cl1 122.09(11) . . ?
C6 C1 Cl1 116.22(12) . . ?
C6 C1 C2 121.66(14) . . ?
C12 C11 C10 120.21(15) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.94(16) . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.69(15) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 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
O1 C13 C16 N1 85.37(13) . . . . ?
O1 C13 C16 C15 -31.81(15) . . . . ?
O1 C13 C16 C2 -155.19(11) . . . . ?
O2 C13 C16 N1 -88.64(16) . . . . ?
O2 C13 C16 C15 154.18(14) . . . . ?
O2 C13 C16 C2 30.79(19) . . . . ?
N1 C17 C22 C23 0.34(15) . . . . ?
N1 C17 C22 C21 178.91(12) . . . . ?
N1 C17 C18 C19 -178.95(14) . . . . ?
N1 C24 C23 C22 -0.32(18) . . . . ?
C7 C15 C16 N1 171.88(11) . . . . ?
C7 C15 C16 C2 48.74(15) . . . . ?
C7 C15 C16 C13 -75.79(15) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C7 C12 C11 C10 -0.8(2) . . . . ?
C15 C7 C8 C9 -179.72(14) . . . . ?
C15 C7 C12 C11 -179.38(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C17 N1 C16 C15 -169.28(12) . . . . ?
C17 N1 C16 C2 -47.70(17) . . . . ?
C17 N1 C16 C13 71.34(15) . . . . ?
C17 N1 C24 C23 0.54(17) . . . . ?
C17 C22 C23 C24 -0.02(17) . . . . ?
C17 C22 C21 C20 0.3(2) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C16 N1 C17 C22 -176.31(12) . . . . ?
C16 N1 C17 C18 2.4(2) . . . . ?
C16 N1 C24 C23 176.34(13) . . . . ?
C16 C2 C3 C4 180.00(14) . . . . ?
C16 C2 C1 Cl1 -3.3(2) . . . . ?
C16 C2 C1 C6 178.73(14) . . . . ?
C22 C17 C18 C19 -0.4(2) . . . . ?
C22 C21 C20 C19 -0.3(2) . . . . ?
C8 C7 C15 C16 76.36(17) . . . . ?
C8 C7 C12 C11 -0.2(2) . . . . ?
C24 N1 C17 C22 -0.53(15) . . . . ?
C24 N1 C17 C18 178.18(14) . . . . ?
C24 N1 C16 C15 15.68(18) . . . . ?
C24 N1 C16 C2 137.26(13) . . . . ?
C24 N1 C16 C13 -103.70(14) . . . . ?
C18 C17 C22 C23 -178.51(13) . . . . ?
C18 C17 C22 C21 0.1(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C3 C2 C16 N1 140.99(13) . . . . ?
C3 C2 C16 C15 -97.31(14) . . . . ?
C3 C2 C16 C13 27.93(17) . . . . ?
C3 C2 C1 Cl1 172.43(11) . . . . ?
C3 C2 C1 C6 -5.5(2) . . . . ?
C3 C4 C5 C6 -3.1(3) . . . . ?
C23 C22 C21 C20 178.41(16) . . . . ?
C12 C7 C15 C16 -104.53(15) . . . . ?
C12 C7 C8 C9 1.2(2) . . . . ?
C21 C22 C23 C24 -178.29(16) . . . . ?
C14 O1 C13 O2 -2.2(2) . . . . ?
C14 O1 C13 C16 -176.39(11) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C1 C2 C16 N1 -43.45(17) . . . . ?
C1 C2 C16 C15 78.25(16) . . . . ?
C1 C2 C16 C13 -156.51(13) . . . . ?
C1 C2 C3 C4 4.1(2) . . . . ?
C1 C6 C5 C4 1.7(3) . . . . ?
C11 C10 C9 C8 -0.1(2) . . . . ?
C5 C6 C1 Cl1 -175.29(13) . . . . ?
C5 C6 C1 C2 2.8(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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.622
