# 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_cyp-238_autored
_database_code_depnum_ccdc_archive 'CCDC 2162244'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2022-03-26 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 6-oxo-6H-isoindolo[2,1-a]indole-10b(11H)-carboxylate'
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2
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      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                   8.9025(3)
_cell_length_b                   5.6087(2)
_cell_length_c                   15.0571(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.429(3)
_cell_angle_gamma                90
_cell_volume                     739.40(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4504
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9220
_cell_measurement_theta_min      5.9720
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5822
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.752
_diffrn_reflns_theta_min         5.051
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -19.00   1.00    1.00    --  -41.76 -57.00 -90.00   96
  2  ω    -52.00  33.00   1.00    1.00    --  -41.76  38.00-120.00   85
  3  ω     33.00  74.00   1.00    3.00    --  106.05 -30.00 -30.00   41
  4  ω     97.00 126.00   1.00    3.00    --  106.05 -30.00 -30.00   29
  5  ω     32.00 103.00   1.00    3.00    --  106.05 -94.00 -30.00   71
  6  ω     39.00 100.00   1.00    3.00    --  106.05 -94.00-120.00   61
  7  ω    109.00 178.00   1.00    3.00    --  106.05  77.00  30.00   69
  8  ω     55.00  83.00   1.00    3.00    --  106.05-125.00-120.00   28
  9  ω     80.00 176.00   1.00    3.00    --  106.05  30.00 -30.00   96
 10  ω    -63.00 -19.00   1.00    1.00    --  -42.01 -57.00-180.00   44
 11  ω    -77.00 -44.00   1.00    1.00    --  -42.01 125.00-120.00   33
 12  ω    -61.00 -33.00   1.00    1.00    --  -42.01 -57.00-120.00   28
 13  ω    -37.00  -7.00   1.00    1.00    --  -42.01 125.00-120.00   30
 14  ω      8.00  33.00   1.00    1.00    --   42.01  83.00-178.91   25
 15  ω     10.00  35.00   1.00    1.00    --   42.01  81.00-125.20   25
 16  ω     34.00  86.00   1.00    1.00    --   42.01  19.00-150.00   52
 17  ω    153.00 178.00   1.00    3.00    --  106.05  61.00 -90.00   25
 18  ω     79.00 105.00   1.00    3.00    --  106.05  61.00 120.00   26
 19  ω     78.00 120.00   1.00    3.00    --  106.05  68.00-146.17   42
 20  ω     78.00 104.00   1.00    3.00    --  106.05  61.00 -60.00   26
 21  ω     79.00 118.00   1.00    3.00    --  106.05  61.00 -90.00   39
 22  ω     77.00 102.00   1.00    3.00    --  106.05  61.00 150.00   25
 23  ω     77.00 105.00   1.00    3.00    --  106.05  61.00-150.00   28
 24  ω     80.00 122.00   1.00    3.00    --  106.05  45.00-150.00   42
 25  ω    152.00 178.00   1.00    3.00    --  106.05  62.00-110.70   26
 26  ω     83.00 109.00   1.00    3.00    --  106.05  45.00 -60.00   26
 27  ω     79.00 105.00   1.00    3.00    --  106.05  61.00-180.00   26
 28  ω    152.00 177.00   1.00    3.00    --  106.05  61.00-120.00   25
 29  ω     77.00 107.00   1.00    3.00    --  106.05  61.00-120.00   30
 30  ω     84.00 110.00   1.00    3.00    --  106.05  45.00 150.00   26
 31  ω     78.00 104.00   1.00    3.00    --  106.05  62.00-110.70   26
 32  ω     76.00 102.00   1.00    3.00    --  106.05  69.00-112.84   26
 33  ω     76.00 102.00   1.00    3.00    --  106.05  68.00 158.64   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1704505000
_diffrn_orient_matrix_UB_12      0.0208421000
_diffrn_orient_matrix_UB_13      0.0057680000
_diffrn_orient_matrix_UB_21      -0.0410791000
_diffrn_orient_matrix_UB_22      0.0054428000
_diffrn_orient_matrix_UB_23      -0.1038412000
_diffrn_orient_matrix_UB_31      -0.0136943000
_diffrn_orient_matrix_UB_32      -0.2740058000
_diffrn_orient_matrix_UB_33      -0.0015649000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                2612
_reflns_number_total             2660
_reflns_odcompleteness_completeness 99.80
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.14(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.043
_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)+(0.0917P)²+0.7211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C10(H10), C1(H1), C13(H13), C12(H12), C11(H11)
1.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.1000(5) 0.8187(8) 0.6807(3) 0.0667(12) Uani 1 1 d . . . . .
N1 N 0.3117(4) 0.6306(7) 0.7628(2) 0.0400(9) Uani 1 1 d . . . . .
O3 O 0.6848(4) 0.3936(8) 0.7608(3) 0.0659(12) Uani 1 1 d . . . . .
O2 O 0.6082(5) 0.7654(8) 0.7661(4) 0.0845(16) Uani 1 1 d . . . . .
C4 C 0.2776(5) 0.6115(9) 0.8510(3) 0.0414(10) Uani 1 1 d . . . . .
C8 C 0.4232(5) 0.4465(8) 0.7497(3) 0.0381(10) Uani 1 1 d . . . . .
C15 C 0.2070(5) 0.6824(10) 0.6849(3) 0.0454(11) Uani 1 1 d . . . . .
C5 C 0.3413(5) 0.4035(9) 0.8908(3) 0.0430(11) Uani 1 1 d . . . . .
C16 C 0.5811(5) 0.5596(10) 0.7606(3) 0.0430(11) Uani 1 1 d . . . . .
C14 C 0.2503(5) 0.5289(10) 0.6139(3) 0.0466(11) Uani 1 1 d . . . . .
C9 C 0.3692(5) 0.3794(9) 0.6509(3) 0.0431(11) Uani 1 1 d . . . . .
C3 C 0.1931(6) 0.7648(11) 0.8944(3) 0.0496(12) Uani 1 1 d . . . . .
H3 H 0.1499 0.9029 0.8666 0.060 Uiso 1 1 calc R U . . .
C17 C 0.8419(6) 0.4664(12) 0.7679(5) 0.0606(15) Uani 1 1 d . . . . .
H17A H 0.8497 0.5953 0.7260 0.073 Uiso 1 1 calc R U . . .
H17B H 0.8819 0.5216 0.8286 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3249(6) 0.3481(11) 0.9784(3) 0.0558(14) Uani 1 1 d . . . . .
H6 H 0.3686 0.2109 1.0067 0.067 Uiso 1 1 calc R U . . .
C2 C 0.1758(6) 0.7039(11) 0.9812(4) 0.0578(14) Uani 1 1 d . . . . .
H2 H 0.1181 0.8020 1.0117 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4230(6) 0.2056(11) 0.5996(4) 0.0542(13) Uani 1 1 d . . . . .
H10 H 0.5030 0.1056 0.6243 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4132(6) 0.2594(10) 0.8238(3) 0.0479(11) Uani 1 1 d . . . . .
H7A H 0.3491 0.1259 0.8000 0.058 Uiso 1 1 calc R U . . .
H7B H 0.5135 0.2010 0.8510 0.058 Uiso 1 1 calc R U . . .
C1 C 0.2412(7) 0.5033(13) 1.0230(4) 0.0624(16) Uani 1 1 d . . . . .
H1 H 0.2298 0.4699 1.0819 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1805(7) 0.5093(13) 0.5241(4) 0.0636(16) Uani 1 1 d . . . . .
H13 H 0.1003 0.6091 0.4994 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2342(7) 0.3373(16) 0.4727(4) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.1902 0.3219 0.4121 0.092 Uiso 1 1 calc R U . . .
C11 C 0.3529(8) 0.1859(13) 0.5096(4) 0.0702(17) Uani 1 1 d . . . . .
H11 H 0.3860 0.0698 0.4735 0.084 Uiso 1 1 calc R U . . .
C18 C 0.9258(8) 0.2651(17) 0.7469(9) 0.123(4) Uani 1 1 d . . . . .
H18A H 0.8884 0.2165 0.6858 0.184 Uiso 1 1 calc R U . . .
H18B H 0.9139 0.1366 0.7872 0.184 Uiso 1 1 calc R U . . .
H18C H 1.0320 0.3062 0.7536 0.184 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
O1 C15 1.214(6) . ?
N1 C4 1.419(6) . ?
N1 C8 1.470(6) . ?
N1 C15 1.390(6) . ?
O3 C16 1.310(6) . ?
O3 C17 1.442(6) . ?
O2 C16 1.179(7) . ?
C4 C5 1.385(7) . ?
C4 C3 1.382(7) . ?
C8 C16 1.524(6) . ?
C8 C9 1.525(6) . ?
C8 C7 1.545(6) . ?
C15 C14 1.477(7) . ?
C5 C6 1.389(7) . ?
C5 C7 1.521(7) . ?
C14 C9 1.386(7) . ?
C14 C13 1.387(7) . ?
C9 C10 1.383(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.386(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.420(10) . ?
C6 H6 0.9300 . ?
C6 C1 1.394(9) . ?
C2 H2 0.9300 . ?
C2 C1 1.367(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.375(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.391(10) . ?
C11 H11 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C4 N1 C8 109.6(4) . . ?
C15 N1 C4 125.5(4) . . ?
C15 N1 C8 113.6(4) . . ?
C16 O3 C17 118.2(5) . . ?
C5 C4 N1 109.2(4) . . ?
C3 C4 N1 128.5(5) . . ?
C3 C4 C5 122.3(4) . . ?
N1 C8 C16 109.0(4) . . ?
N1 C8 C9 101.7(4) . . ?
N1 C8 C7 104.6(3) . . ?
C16 C8 C9 109.2(4) . . ?
C16 C8 C7 112.2(4) . . ?
C9 C8 C7 119.1(4) . . ?
O1 C15 N1 125.2(5) . . ?
O1 C15 C14 129.4(4) . . ?
N1 C15 C14 105.4(4) . . ?
C4 C5 C6 119.6(5) . . ?
C4 C5 C7 110.4(4) . . ?
C6 C5 C7 129.8(5) . . ?
O3 C16 C8 109.9(4) . . ?
O2 C16 O3 124.1(5) . . ?
O2 C16 C8 126.0(5) . . ?
C9 C14 C15 110.0(4) . . ?
C9 C14 C13 121.3(5) . . ?
C13 C14 C15 128.5(5) . . ?
C14 C9 C8 109.0(4) . . ?
C10 C9 C8 129.8(5) . . ?
C10 C9 C14 121.2(5) . . ?
C4 C3 H3 121.5 . . ?
C4 C3 C2 117.1(5) . . ?
C2 C3 H3 121.5 . . ?
O3 C17 H17A 110.2 . . ?
O3 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 O3 107.5(6) . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C1 118.3(5) . . ?
C1 C6 H6 120.8 . . ?
C3 C2 H2 119.1 . . ?
C1 C2 C3 121.8(5) . . ?
C1 C2 H2 119.1 . . ?
C9 C10 H10 121.3 . . ?
C9 C10 C11 117.5(6) . . ?
C11 C10 H10 121.3 . . ?
C8 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C5 C7 C8 101.8(4) . . ?
C5 C7 H7A 111.4 . . ?
C5 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 H1 119.6 . . ?
C14 C13 H13 121.2 . . ?
C12 C13 C14 117.7(6) . . ?
C12 C13 H13 121.2 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.3(5) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 C12 121.0(6) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C15 C14 C9 -172.4(6) . . . . ?
O1 C15 C14 C13 2.0(10) . . . . ?
N1 C4 C5 C6 179.0(4) . . . . ?
N1 C4 C5 C7 -4.7(5) . . . . ?
N1 C4 C3 C2 179.5(5) . . . . ?
N1 C8 C16 O3 171.9(4) . . . . ?
N1 C8 C16 O2 -9.5(8) . . . . ?
N1 C8 C9 C14 5.0(5) . . . . ?
N1 C8 C9 C10 -176.1(5) . . . . ?
N1 C8 C7 C5 -20.3(5) . . . . ?
N1 C15 C14 C9 4.4(6) . . . . ?
N1 C15 C14 C13 178.8(6) . . . . ?
C4 N1 C8 C16 -101.1(4) . . . . ?
C4 N1 C8 C9 143.7(4) . . . . ?
C4 N1 C8 C7 19.1(5) . . . . ?
C4 N1 C15 O1 36.2(8) . . . . ?
C4 N1 C15 C14 -140.7(5) . . . . ?
C4 C5 C6 C1 1.3(8) . . . . ?
C4 C5 C7 C8 15.9(5) . . . . ?
C4 C3 C2 C1 1.1(8) . . . . ?
C8 N1 C4 C5 -9.5(5) . . . . ?
C8 N1 C4 C3 171.7(5) . . . . ?
C8 N1 C15 O1 175.9(5) . . . . ?
C8 N1 C15 C14 -1.0(5) . . . . ?
C8 C9 C10 C11 -179.0(5) . . . . ?
C15 N1 C4 C5 131.5(5) . . . . ?
C15 N1 C4 C3 -47.3(7) . . . . ?
C15 N1 C8 C16 112.9(4) . . . . ?
C15 N1 C8 C9 -2.3(5) . . . . ?
C15 N1 C8 C7 -126.9(4) . . . . ?
C15 C14 C9 C8 -6.0(6) . . . . ?
C15 C14 C9 C10 175.0(5) . . . . ?
C15 C14 C13 C12 -174.3(6) . . . . ?
C5 C4 C3 C2 0.9(7) . . . . ?
C5 C6 C1 C2 0.6(9) . . . . ?
C16 O3 C17 C18 -167.4(7) . . . . ?
C16 C8 C9 C14 -110.1(4) . . . . ?
C16 C8 C9 C10 68.8(7) . . . . ?
C16 C8 C7 C5 97.7(4) . . . . ?
C14 C9 C10 C11 -0.2(8) . . . . ?
C14 C13 C12 C11 0.8(11) . . . . ?
C9 C8 C16 O3 -77.9(5) . . . . ?
C9 C8 C16 O2 100.7(7) . . . . ?
C9 C8 C7 C5 -132.9(4) . . . . ?
C9 C14 C13 C12 -0.5(9) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C3 C4 C5 C6 -2.1(7) . . . . ?
C3 C4 C5 C7 174.1(5) . . . . ?
C3 C2 C1 C6 -1.9(9) . . . . ?
C17 O3 C16 O2 -0.3(9) . . . . ?
C17 O3 C16 C8 178.3(4) . . . . ?
C6 C5 C7 C8 -168.4(5) . . . . ?
C7 C8 C16 O3 56.5(5) . . . . ?
C7 C8 C16 O2 -124.9(7) . . . . ?
C7 C8 C9 C14 119.2(5) . . . . ?
C7 C8 C9 C10 -61.9(7) . . . . ?
C7 C5 C6 C1 -174.1(5) . . . . ?
C13 C14 C9 C8 179.2(5) . . . . ?
C13 C14 C9 C10 0.2(8) . . . . ?
C13 C12 C11 C10 -0.9(12) . . . . ?

_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.813
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
####################################################################### 
# 
# 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_238_auto
_database_code_depnum_ccdc_archive 'CCDC 2183419'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 1-(2-bromobenzoyl)-1H-indole-2-carboxylate'
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2Br1
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      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                   7.8811(6)
_cell_length_b                   10.3618(5)
_cell_length_c                   10.9560(8)
_cell_angle_alpha                66.055(6)
_cell_angle_beta                 78.039(6)
_cell_angle_gamma                88.232(5)
_cell_volume                     798.52(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0200
_cell_measurement_theta_min      4.5050
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.234
_diffrn_reflns_theta_min         4.520
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -21.00   1.00    1.00    --  -41.76 -57.00 -30.00   86
  2  ω    -60.00  33.00   1.00    1.00    --  -41.76  38.00 -90.00   93
  3  ω    -19.00  30.00   1.00    1.00    --  -41.76  57.00 120.00   49
  4  ω    -69.00 -30.00   1.00    1.00    --  -41.76  57.00 120.00   39
  5  ω    -85.00 -56.00   1.00    1.00    --  -41.76 124.00-177.00   29
  6  ω     27.00  62.00   1.00    1.00    --   41.76-125.00-180.00   35
  7  ω     43.00 121.00   1.00    3.00    --  106.05 -45.00-180.00   78
  8  ω     39.00 112.00   1.00    3.00    --  106.05-125.00   0.00   73
  9  ω     24.00  64.00   1.00    3.00    --  106.05 -94.00   0.00   40
 10  ω     30.00  61.00   1.00    3.00    --  106.05 -94.00  60.00   31
 11  ω     98.00 123.00   1.00    3.00    --  106.05 -77.00 150.00   25
 12  ω     44.00 123.00   1.00    3.00    --  106.05 -45.00  90.00   79
 13  ω     63.00 107.00   1.00    3.00    --  106.05 -94.00-180.00   44
 14  ω     24.00 106.00   1.00    3.00    --  106.05 -94.00  90.00   82
 15  ω    111.00 176.00   1.00    3.00    --  106.05  77.00 150.00   65
 16  ω    110.00 176.00   1.00    3.00    --  106.05  77.00-120.00   66
 17  ω     70.00 107.00   1.00    3.00    --  106.05 -94.00   0.00   37
 18  ω    108.00 175.00   1.00    3.00    --  106.05   0.00  60.00   67
 19  ω     21.00  84.00   1.00    3.00    --  106.05   0.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0931630000
_diffrn_orient_matrix_UB_12      0.0285764000
_diffrn_orient_matrix_UB_13      0.1240424000
_diffrn_orient_matrix_UB_21      -0.0715928000
_diffrn_orient_matrix_UB_22      0.1343154000
_diffrn_orient_matrix_UB_23      -0.0961857000
_diffrn_orient_matrix_UB_31      -0.1620568000
_diffrn_orient_matrix_UB_32      -0.0877570000
_diffrn_orient_matrix_UB_33      0.0126449000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2967
_reflns_number_total             3096
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.655
_refine_diff_density_min         -1.145
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.029
_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)+(0.0985P)²+1.5710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1707
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C11(H11), C7(H7), C6(H6), C14(H14), C12(H12), C13(H13)
1.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.15661(7) -0.12122(5) 0.95501(4) 0.0561(2) Uani 1 1 d . . . . .
O3 O 0.3596(4) 0.4646(3) 0.7232(3) 0.0497(7) Uani 1 1 d . . . . .
O1 O 0.1245(5) 0.0179(3) 0.6426(4) 0.0588(9) Uani 1 1 d . . . . .
O2 O 0.2295(5) 0.2456(3) 0.8391(3) 0.0519(7) Uani 1 1 d . . . . .
N1 N 0.2014(4) 0.2493(3) 0.5748(3) 0.0360(7) Uani 1 1 d . . . . .
C2 C 0.2480(5) 0.4868(4) 0.4903(4) 0.0417(8) Uani 1 1 d . . . . .
H2 H 0.2775 0.5768 0.4816 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1535(5) 0.3077(4) 0.4458(4) 0.0360(7) Uani 1 1 d . . . . .
C1 C 0.2585(5) 0.3630(4) 0.5982(4) 0.0362(7) Uani 1 1 d . . . . .
C10 C 0.3783(5) 0.0659(4) 0.7053(4) 0.0385(8) Uani 1 1 d . . . . .
C9 C 0.2222(5) 0.1038(4) 0.6442(4) 0.0388(8) Uani 1 1 d . . . . .
C16 C 0.2809(5) 0.3468(4) 0.7337(4) 0.0395(8) Uani 1 1 d . . . . .
C15 C 0.3738(6) -0.0372(4) 0.8361(4) 0.0416(8) Uani 1 1 d . . . . .
C3 C 0.1838(5) 0.4544(4) 0.3932(4) 0.0388(8) Uani 1 1 d . . . . .
C5 C 0.0937(6) 0.2409(5) 0.3748(4) 0.0459(9) Uani 1 1 d . . . . .
H5 H 0.0749 0.1431 0.4108 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1505(6) 0.5387(5) 0.2636(4) 0.0495(10) Uani 1 1 d . . . . .
H8 H 0.1687 0.6366 0.2269 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3730(7) 0.4705(6) 0.8507(5) 0.0568(11) Uani 1 1 d . . . . .
H17A H 0.4626 0.4106 0.8885 0.068 Uiso 1 1 calc R U . . .
H17B H 0.2635 0.4380 0.9166 0.068 Uiso 1 1 calc R U . . .
C11 C 0.5391(6) 0.1271(5) 0.6242(5) 0.0515(10) Uani 1 1 d . . . . .
H11 H 0.5459 0.1960 0.5362 0.062 Uiso 1 1 calc R U . . .
C7 C 0.0913(6) 0.4739(5) 0.1932(5) 0.0556(11) Uani 1 1 d . . . . .
H7 H 0.0690 0.5286 0.1075 0.067 Uiso 1 1 calc R U . . .
C6 C 0.0634(6) 0.3274(6) 0.2469(5) 0.0546(11) Uani 1 1 d . . . . .
H6 H 0.0234 0.2865 0.1959 0.065 Uiso 1 1 calc R U . . .
C14 C 0.5223(7) -0.0754(5) 0.8855(6) 0.0571(12) Uani 1 1 d . . . . .
H14 H 0.5160 -0.1424 0.9744 0.068 Uiso 1 1 calc R U . . .
C18 C 0.4178(7) 0.6212(6) 0.8199(6) 0.0635(13) Uani 1 1 d . . . . .
H18A H 0.5300 0.6501 0.7596 0.095 Uiso 1 1 calc R U . . .
H18B H 0.4200 0.6302 0.9034 0.095 Uiso 1 1 calc R U . . .
H18C H 0.3322 0.6801 0.7770 0.095 Uiso 1 1 calc R U . . .
C12 C 0.6886(6) 0.0868(6) 0.6725(7) 0.0659(14) Uani 1 1 d . . . . .
H12 H 0.7958 0.1279 0.6168 0.079 Uiso 1 1 calc R U . . .
C13 C 0.6801(7) -0.0143(6) 0.8032(7) 0.0676(15) Uani 1 1 d . . . . .
H13 H 0.7815 -0.0411 0.8357 0.081 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 C15 1.905(4) . ?
O3 C16 1.338(5) . ?
O3 C17 1.448(5) . ?
O1 C9 1.202(5) . ?
O2 C16 1.202(5) . ?
N1 C4 1.421(5) . ?
N1 C1 1.408(5) . ?
N1 C9 1.409(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.361(6) . ?
C2 C3 1.423(6) . ?
C4 C3 1.398(5) . ?
C4 C5 1.384(6) . ?
C1 C16 1.473(5) . ?
C10 C9 1.488(5) . ?
C10 C15 1.391(5) . ?
C10 C11 1.387(6) . ?
C15 C14 1.371(6) . ?
C3 C8 1.407(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.361(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.495(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.393(7) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.372(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.378(9) . ?
C13 H13 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
C16 O3 C17 116.0(3) . . ?
C1 N1 C4 107.1(3) . . ?
C1 N1 C9 128.6(3) . . ?
C9 N1 C4 122.8(3) . . ?
C1 C2 H2 126.0 . . ?
C1 C2 C3 108.0(3) . . ?
C3 C2 H2 126.0 . . ?
C3 C4 N1 107.4(3) . . ?
C5 C4 N1 129.9(4) . . ?
C5 C4 C3 122.7(4) . . ?
N1 C1 C16 122.2(3) . . ?
C2 C1 N1 109.5(3) . . ?
C2 C1 C16 126.5(3) . . ?
C15 C10 C9 123.3(4) . . ?
C11 C10 C9 118.6(4) . . ?
C11 C10 C15 117.8(4) . . ?
O1 C9 N1 120.1(4) . . ?
O1 C9 C10 123.3(4) . . ?
N1 C9 C10 116.3(3) . . ?
O3 C16 C1 109.8(3) . . ?
O2 C16 O3 124.9(4) . . ?
O2 C16 C1 125.3(4) . . ?
C10 C15 Br1 120.0(3) . . ?
C14 C15 Br1 118.3(3) . . ?
C14 C15 C10 121.5(4) . . ?
C4 C3 C2 108.0(3) . . ?
C4 C3 C8 119.2(4) . . ?
C8 C3 C2 132.9(4) . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.5(4) . . ?
C6 C5 H5 121.7 . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.6(4) . . ?
C7 C8 H8 120.7 . . ?
O3 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
O3 C17 C18 107.2(4) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.6 . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C6 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?

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 C15 C14 C13 -178.5(4) . . . . ?
N1 C4 C3 C2 -0.8(4) . . . . ?
N1 C4 C3 C8 178.6(4) . . . . ?
N1 C4 C5 C6 -177.7(4) . . . . ?
N1 C1 C16 O3 171.1(3) . . . . ?
N1 C1 C16 O2 -12.0(6) . . . . ?
C2 C1 C16 O3 -25.5(6) . . . . ?
C2 C1 C16 O2 151.4(4) . . . . ?
C2 C3 C8 C7 178.6(4) . . . . ?
C4 N1 C1 C2 -0.1(4) . . . . ?
C4 N1 C1 C16 165.8(3) . . . . ?
C4 N1 C9 O1 -38.8(6) . . . . ?
C4 N1 C9 C10 135.5(4) . . . . ?
C4 C3 C8 C7 -0.6(6) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C1 N1 C4 C3 0.6(4) . . . . ?
C1 N1 C4 C5 178.1(4) . . . . ?
C1 N1 C9 O1 157.1(4) . . . . ?
C1 N1 C9 C10 -28.7(6) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C2 C3 C8 -178.5(4) . . . . ?
C10 C15 C14 C13 -2.1(7) . . . . ?
C10 C11 C12 C13 -0.6(8) . . . . ?
C9 N1 C4 C3 -166.5(3) . . . . ?
C9 N1 C4 C5 11.0(6) . . . . ?
C9 N1 C1 C2 166.0(4) . . . . ?
C9 N1 C1 C16 -28.0(6) . . . . ?
C9 C10 C15 Br1 -7.9(5) . . . . ?
C9 C10 C15 C14 175.8(4) . . . . ?
C9 C10 C11 C12 -174.7(4) . . . . ?
C16 O3 C17 C18 -164.7(4) . . . . ?
C15 C10 C9 O1 -50.2(6) . . . . ?
C15 C10 C9 N1 135.7(4) . . . . ?
C15 C10 C11 C12 -0.3(7) . . . . ?
C15 C14 C13 C12 1.2(8) . . . . ?
C3 C2 C1 N1 -0.4(5) . . . . ?
C3 C2 C1 C16 -165.6(4) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C3 C8 C7 C6 0.1(7) . . . . ?
C5 C4 C3 C2 -178.6(4) . . . . ?
C5 C4 C3 C8 0.8(6) . . . . ?
C8 C7 C6 C5 0.3(8) . . . . ?
C17 O3 C16 O2 -3.6(6) . . . . ?
C17 O3 C16 C1 173.3(4) . . . . ?
C11 C10 C9 O1 123.9(5) . . . . ?
C11 C10 C9 N1 -50.2(5) . . . . ?
C11 C10 C15 Br1 178.0(3) . . . . ?
C11 C10 C15 C14 1.7(6) . . . . ?
C11 C12 C13 C14 0.2(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 2.036
_oxdiff_exptl_absorpt_empirical_full_min 0.613
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
