# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_sw
_database_code_depnum_ccdc_archive 'CCDC 2109801'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2021-09-14 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 Br N2'
_chemical_formula_sum            'C23 H15 Br N2'
_chemical_formula_weight         399.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H15BrN2
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'

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

_cell_length_a                   45.2994(6)
_cell_length_b                   6.08550(10)
_cell_length_c                   12.8728(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.7350(10)
_cell_angle_gamma                90
_cell_volume                     3544.60(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11250
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7620
_cell_measurement_theta_min      3.8870
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    3.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.559
_diffrn_reflns_theta_min         3.908
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -25.00   0.50    1.23    --  -47.08 -74.00 120.00  188
  2  ω    -69.00  26.00   0.50    1.23    --  -47.08  74.00-110.00  190
  3  ω    -25.00  70.00   0.50    1.23    --   47.08 -74.00 120.00  190
  4  ω     25.00 120.00   0.50    1.23    --   47.08  74.00-110.00  190
  5  ω    -92.00 -19.00   0.50    4.92    --  -91.75  74.00-110.00  146
  6  ω   -164.00 -69.00   0.50    4.92    --  -91.75 -74.00 120.00  190
  7  ω     91.00 178.00   0.50    4.92    --  113.25  74.00-110.00  174
  8  ω     41.00 106.00   0.50    4.92    --  113.25 -74.00 120.00  130
  9  ω   -119.00 -73.00   0.50    1.23    --  -47.08-125.00-150.00   92
 10  ω   -119.00 -73.00   0.50    1.23    --  -47.08-125.00 -60.00   92
 11  ω    -16.00  28.00   0.50    1.23    --  -47.08  19.00  60.00   88
 12  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00 -30.00   76
 13  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00-180.00   76
 14  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00   0.00   76
 15  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00 120.00   76
 16  ω     99.00 178.00   0.50    4.92    --  113.25  30.00-150.00  158
 17  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00-150.00   76
 18  ω     96.00 178.00   0.50    4.92    --  113.25  15.00 -30.00  164
 19  ω     41.00 106.00   0.50    4.92    --  113.25 -94.00-180.00  130
 20  ω     96.00 178.00   0.50    4.92    --  113.25  61.00   0.00  164
 21  ω     99.00 178.00   0.50    4.92    --  113.25  30.00 -30.00  158
 22  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00  30.00   76
 23  ω     41.00 111.00   0.50    4.92    --  113.25-125.00 -90.00  140
 24  ω     96.00 178.00   0.50    4.92    --  113.25  15.00-180.00  164
 25  ω     99.00 178.00   0.50    4.92    --  113.25  30.00  30.00  158
 26  ω     41.00  79.00   0.50    4.92    --  113.25 -61.00 -90.00   76
 27  ω   -119.00 -23.00   0.50    1.23    --  -47.08 -77.00 -30.00  192
 28  ω   -121.00 -32.00   0.50    1.23    --  -47.08 -37.00 150.00  178
 29  ω   -119.00 -56.00   0.50    1.23    --  -47.08 -77.00  60.00  126
 30  ω   -119.00 -39.00   0.50    1.23    --  -47.08 -77.00  30.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124167000
_diffrn_orient_matrix_UB_12      -0.2067450000
_diffrn_orient_matrix_UB_13      0.0514808000
_diffrn_orient_matrix_UB_21      -0.0240757000
_diffrn_orient_matrix_UB_22      -0.0176419000
_diffrn_orient_matrix_UB_23      -0.0882484000
_diffrn_orient_matrix_UB_31      0.0206226000
_diffrn_orient_matrix_UB_32      -0.1449620000
_diffrn_orient_matrix_UB_33      -0.0626275000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3390
_reflns_number_total             3794
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+12.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 H11-C11
 0.91 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73370(2) 0.85121(7) 0.11294(3) 0.04598(16) Uani 1 1 d . . . . .
N1 N 0.65178(6) -0.0611(5) 0.6574(2) 0.0374(6) Uani 1 1 d . . . . .
N2 N 0.64922(5) 0.3415(4) 0.4748(2) 0.0291(5) Uani 1 1 d . . . . .
C1 C 0.59883(6) 0.2766(5) 0.5396(2) 0.0256(5) Uani 1 1 d . . . . .
C2 C 0.57900(6) 0.4236(5) 0.5846(2) 0.0260(6) Uani 1 1 d . . . . .
C3 C 0.58784(7) 0.6126(5) 0.6446(2) 0.0284(6) Uani 1 1 d . . . . .
H3 H 0.6086(9) 0.644(6) 0.650(3) 0.034(10) Uiso 1 1 d . . . . .
C4 C 0.56778(7) 0.7498(5) 0.6857(2) 0.0302(6) Uani 1 1 d . . . . .
H4 H 0.5742(8) 0.870(6) 0.717(3) 0.025(8) Uiso 1 1 d . . . . .
C5 C 0.53700(7) 0.7073(5) 0.6724(2) 0.0314(6) Uani 1 1 d . . . . .
H5 H 0.5228(8) 0.802(6) 0.703(3) 0.026(8) Uiso 1 1 d . . . . .
C6 C 0.52740(7) 0.5293(5) 0.6165(2) 0.0306(6) Uani 1 1 d . . . . .
H6 H 0.5072(9) 0.502(7) 0.610(3) 0.041(10) Uiso 1 1 d . . . . .
C7 C 0.54770(6) 0.3858(5) 0.5688(2) 0.0264(6) Uani 1 1 d . . . . .
C8 C 0.53779(6) 0.2102(5) 0.5073(2) 0.0268(6) Uani 1 1 d . . . . .
H8 H 0.5172(8) 0.198(6) 0.501(3) 0.031(9) Uiso 1 1 d . . . . .
C9 C 0.55715(6) 0.0694(5) 0.4589(2) 0.0265(6) Uani 1 1 d . . . . .
C10 C 0.54658(7) -0.1116(5) 0.3967(2) 0.0290(6) Uani 1 1 d . . . . .
H10 H 0.5265(8) -0.124(5) 0.388(3) 0.022(8) Uiso 1 1 d . . . . .
C11 C 0.56556(7) -0.2518(5) 0.3528(2) 0.0295(6) Uani 1 1 d D . . . .
H11 H 0.5576(8) -0.364(5) 0.316(3) 0.036(10) Uiso 1 1 d D . . . .
C12 C 0.59640(7) -0.2159(5) 0.3652(2) 0.0295(6) Uani 1 1 d . . . . .
H12 H 0.6091(9) -0.316(6) 0.335(3) 0.035(10) Uiso 1 1 d . . . . .
C13 C 0.60753(6) -0.0446(5) 0.4233(2) 0.0277(6) Uani 1 1 d . . . . .
H13 H 0.6283(8) -0.013(6) 0.425(3) 0.033(9) Uiso 1 1 d . . . . .
C14 C 0.58846(6) 0.1027(5) 0.4742(2) 0.0258(6) Uani 1 1 d . . . . .
C15 C 0.63190(6) 0.2994(5) 0.5665(2) 0.0276(6) Uani 1 1 d . . . . .
H15 H 0.6361(8) 0.400(6) 0.617(3) 0.030(9) Uiso 1 1 d . . . . .
C16 C 0.64316(7) 0.0949(5) 0.6167(2) 0.0303(6) Uani 1 1 d . . . . .
C17 C 0.66159(6) 0.5298(5) 0.4732(2) 0.0297(6) Uani 1 1 d . . . . .
H17 H 0.6595(9) 0.633(7) 0.525(3) 0.042(11) Uiso 1 1 d . . . . .
C18 C 0.67932(6) 0.6009(5) 0.3873(2) 0.0299(6) Uani 1 1 d . . . . .
C19 C 0.68299(7) 0.4672(5) 0.3010(2) 0.0325(6) Uani 1 1 d . . . . .
H19 H 0.6730(9) 0.327(6) 0.303(3) 0.037(10) Uiso 1 1 d . . . . .
C20 C 0.69975(7) 0.5404(6) 0.2202(3) 0.0354(7) Uani 1 1 d . . . . .
H20 H 0.7035(8) 0.443(7) 0.163(3) 0.039(10) Uiso 1 1 d . . . . .
C21 C 0.71225(7) 0.7468(6) 0.2267(2) 0.0351(7) Uani 1 1 d . . . . .
C22 C 0.70954(7) 0.8817(6) 0.3120(3) 0.0375(7) Uani 1 1 d . . . . .
H22 H 0.7183(11) 1.024(9) 0.307(4) 0.069(15) Uiso 1 1 d . . . . .
C23 C 0.69279(7) 0.8079(5) 0.3919(3) 0.0340(7) Uani 1 1 d . . . . .
H23 H 0.6908(8) 0.900(6) 0.453(3) 0.037(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C21 1.905(3) . ?
N1 C16 1.143(4) . ?
N2 C15 1.470(4) . ?
N2 C17 1.276(4) . ?
C1 C2 1.411(4) . ?
C1 C14 1.419(4) . ?
C1 C15 1.528(4) . ?
C2 C3 1.432(4) . ?
C2 C7 1.441(4) . ?
C3 H3 0.96(4) . ?
C3 C4 1.360(4) . ?
C4 H4 0.88(4) . ?
C4 C5 1.420(4) . ?
C5 H5 0.96(4) . ?
C5 C6 1.360(5) . ?
C6 H6 0.93(4) . ?
C6 C7 1.429(4) . ?
C7 C8 1.392(4) . ?
C8 H8 0.94(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.432(4) . ?
C9 C14 1.437(4) . ?
C10 H10 0.91(4) . ?
C10 C11 1.354(4) . ?
C11 H11 0.894(18) . ?
C11 C12 1.416(4) . ?
C12 H12 0.93(4) . ?
C12 C13 1.365(4) . ?
C13 H13 0.96(4) . ?
C13 C14 1.425(4) . ?
C15 H15 0.91(4) . ?
C15 C16 1.482(4) . ?
C17 H17 0.92(4) . ?
C17 C18 1.463(4) . ?
C18 C19 1.394(4) . ?
C18 C23 1.399(4) . ?
C19 H19 0.96(4) . ?
C19 C20 1.390(5) . ?
C20 H20 0.97(4) . ?
C20 C21 1.379(5) . ?
C21 C22 1.381(5) . ?
C22 H22 0.95(6) . ?
C22 C23 1.382(5) . ?
C23 H23 0.97(4) . ?

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
C17 N2 C15 114.9(3) . . ?
C2 C1 C14 121.2(3) . . ?
C2 C1 C15 119.1(3) . . ?
C14 C1 C15 119.7(3) . . ?
C1 C2 C3 124.3(3) . . ?
C1 C2 C7 118.8(3) . . ?
C3 C2 C7 116.9(3) . . ?
C2 C3 H3 117(2) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 121(2) . . ?
C3 C4 H4 119(2) . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 120(2) . . ?
C4 C5 H5 121(2) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 119(2) . . ?
C5 C6 H6 119(3) . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 120(3) . . ?
C6 C7 C2 119.4(3) . . ?
C8 C7 C2 119.4(3) . . ?
C8 C7 C6 121.2(3) . . ?
C7 C8 H8 114(2) . . ?
C7 C8 C9 122.2(3) . . ?
C9 C8 H8 124(2) . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 C14 119.4(3) . . ?
C10 C9 C14 119.1(3) . . ?
C9 C10 H10 116(2) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 123(2) . . ?
C10 C11 H11 117(3) . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 123(3) . . ?
C11 C12 H12 118(2) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 120(2) . . ?
C12 C13 H13 120(2) . . ?
C12 C13 C14 121.1(3) . . ?
C14 C13 H13 119(2) . . ?
C1 C14 C9 118.9(3) . . ?
C1 C14 C13 123.4(3) . . ?
C13 C14 C9 117.7(3) . . ?
N2 C15 C1 112.9(2) . . ?
N2 C15 H15 111(2) . . ?
N2 C15 C16 108.1(2) . . ?
C1 C15 H15 113(2) . . ?
C16 C15 C1 109.6(2) . . ?
C16 C15 H15 101(2) . . ?
N1 C16 C15 178.7(4) . . ?
N2 C17 H17 123(3) . . ?
N2 C17 C18 122.3(3) . . ?
C18 C17 H17 115(3) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 C23 119.4(3) . . ?
C23 C18 C17 119.3(3) . . ?
C18 C19 H19 115(2) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 125(2) . . ?
C19 C20 H20 120(2) . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 121(2) . . ?
C20 C21 Br1 118.7(3) . . ?
C20 C21 C22 122.5(3) . . ?
C22 C21 Br1 118.8(3) . . ?
C21 C22 H22 116(3) . . ?
C21 C22 C23 118.1(3) . . ?
C23 C22 H22 126(3) . . ?
C18 C23 H23 120(2) . . ?
C22 C23 C18 121.0(3) . . ?
C22 C23 H23 119(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
Br1 C21 C22 C23 177.1(2) . . . . ?
N2 C17 C18 C19 1.6(5) . . . . ?
N2 C17 C18 C23 -178.6(3) . . . . ?
C1 C2 C3 C4 179.6(3) . . . . ?
C1 C2 C7 C6 178.1(3) . . . . ?
C1 C2 C7 C8 -1.9(4) . . . . ?
C2 C1 C14 C9 -3.7(4) . . . . ?
C2 C1 C14 C13 177.3(3) . . . . ?
C2 C1 C15 N2 -120.1(3) . . . . ?
C2 C1 C15 C16 119.3(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C2 C7 C8 C9 -0.7(4) . . . . ?
C3 C2 C7 C6 -2.8(4) . . . . ?
C3 C2 C7 C8 177.2(3) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C5 C6 C7 C2 3.3(4) . . . . ?
C5 C6 C7 C8 -176.7(3) . . . . ?
C6 C7 C8 C9 179.3(3) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C7 C8 C9 C14 1.2(4) . . . . ?
C8 C9 C10 C11 -177.8(3) . . . . ?
C8 C9 C14 C1 1.0(4) . . . . ?
C8 C9 C14 C13 -180.0(3) . . . . ?
C9 C10 C11 C12 -2.2(4) . . . . ?
C10 C9 C14 C1 -177.3(3) . . . . ?
C10 C9 C14 C13 1.8(4) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C1 176.8(3) . . . . ?
C12 C13 C14 C9 -2.2(4) . . . . ?
C14 C1 C2 C3 -174.9(3) . . . . ?
C14 C1 C2 C7 4.2(4) . . . . ?
C14 C1 C15 N2 62.8(3) . . . . ?
C14 C1 C15 C16 -57.8(3) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C15 N2 C17 C18 -179.1(3) . . . . ?
C15 C1 C2 C3 8.1(4) . . . . ?
C15 C1 C2 C7 -172.8(2) . . . . ?
C15 C1 C14 C9 173.3(2) . . . . ?
C15 C1 C14 C13 -5.7(4) . . . . ?
C17 N2 C15 C1 114.1(3) . . . . ?
C17 N2 C15 C16 -124.5(3) . . . . ?
C17 C18 C19 C20 179.4(3) . . . . ?
C17 C18 C23 C22 -179.6(3) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C19 C18 C23 C22 0.2(5) . . . . ?
C19 C20 C21 Br1 -177.2(2) . . . . ?
C19 C20 C21 C22 2.0(5) . . . . ?
C20 C21 C22 C23 -2.2(5) . . . . ?
C21 C22 C23 C18 1.0(5) . . . . ?
C23 C18 C19 C20 -0.4(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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_soh
_database_code_depnum_ccdc_archive 'CCDC 2224125'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;memorial university of newfoundland
Canada
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H20 N2'
_chemical_formula_sum            'C31 H20 N2'
_chemical_formula_weight         420.49
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31 H20 N2'
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'

_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.18100(10)
_cell_length_b                   9.6048(2)
_cell_length_c                   11.9887(3)
_cell_angle_alpha                67.824(2)
_cell_angle_beta                 85.664(2)
_cell_angle_gamma                78.436(2)
_cell_volume                     541.24(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    10439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1480
_cell_measurement_theta_min      3.9840
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -1 0.0366
-2 -1 4 0.0661
-1 6 4 0.0242
2 1 -4 0.0095
-1 0 7 0.0444
-1 -4 -7 0.0169
3 4 1 0.0176
0 4 -4 0.0026
-1 -2 5 0.0467
3 0 4 0.0471
0 0 -7 0.0053

_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0012 -1.9991 -1.0009 -0.0083 -0.3182 -0.0764
-2.3860 -1.4456 4.3547 0.0033 0.1601 -0.9871
-0.5766 5.6853 4.0781 0.0262 0.9996 -0.0090
2.3900 1.2789 -4.4467 -0.0040 -0.1873 0.9823
-1.1118 0.1158 6.8272 -0.4268 0.3266 -0.8433
-1.2945 -3.6589 -7.2174 0.7877 -0.6044 0.1194
2.8140 4.1552 0.5033 -0.4260 0.3279 0.8432
0.0950 3.6261 -4.1175 0.5771 0.3974 0.7134
-1.1974 -2.3772 5.2166 -0.3838 -0.0720 -0.9206
2.7454 -0.0763 3.9196 -0.9723 -0.1800 0.1491
0.2555 -0.4824 -7.3805 0.6436 -0.3078 0.7007

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17194
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.280
_diffrn_reflns_theta_min         3.982
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -33.00   0.50    5.00    --  -48.54 -63.00  95.00  174
  2  ω     33.00 121.00   0.50    5.00    --   48.54  63.00-127.00  176
  3  ω    -23.00  65.00   0.50    5.00    --   48.54 -63.00  95.00  176
  4  ω    -68.00 -18.00   0.50   15.00    --  -90.00  63.00-127.00  100
  5  ω   -161.00 -74.00   0.50   15.00    --  -90.00 -63.00  95.00  174
  6  ω     96.00 178.00   0.50   15.00    --  111.50  63.00-127.00  164
  7  ω     40.00  82.00   0.50   15.00    --  111.50 -63.00  95.00   84
  8  ω    -64.00  24.00   0.50    5.00    --  -48.54  63.00-127.00  176
  9  ω     34.00  95.00   0.50    5.00    --   48.54-125.00 -30.00  122
 10  ω    -25.00  30.00   0.50    5.00    --   48.54 -19.00   0.00  110
 11  ω    -25.00  30.00   0.50    5.00    --   48.54 -19.00  90.00  110
 12  ω   -161.00 -83.00   0.50   15.00    --  -90.00 -94.00   0.00  156
 13  ω    -65.00 -18.00   0.50   15.00    --  -90.00  61.00  60.00   94
 14  ω    -65.00 -18.00   0.50   15.00    --  -90.00  61.00  30.00   94
 15  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00  30.00  130
 16  ω     40.00  79.00   0.50   15.00    --  111.50 -61.00 150.00   78
 17  ω     95.00 178.00   0.50   15.00    --  111.50 125.00  60.00  166
 18  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00 120.00  130
 19  ω     40.00 111.00   0.50   15.00    --  111.50-125.00-150.00  142
 20  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00   0.00  130
 21  ω     40.00 106.00   0.50   15.00    --  111.50 -93.00-148.71  132
 22  ω    101.00 178.00   0.50   15.00    --  111.50  15.00  30.00  154
 23  ω     40.00  79.00   0.50   15.00    --  111.50 -61.00  30.00   78
 24  ω     40.00 111.00   0.50   15.00    --  111.50-125.00 -60.00  142
 25  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00  60.00  130
 26  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00  90.00  130
 27  ω     40.00  79.00   0.50   15.00    --  111.50 -61.00-150.00   78
 28  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00 -60.00  130
 29  ω    101.00 178.00   0.50   15.00    --  111.50  45.00 -60.00  154
 30  ω    101.00 178.00   0.50   15.00    --  111.50  45.00 150.00  154
 31  ω    101.00 178.00   0.50   15.00    --  111.50  45.00  60.00  154
 32  ω     40.00 111.00   0.50   15.00    --  111.50-125.00 -90.00  142
 33  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00 -30.00  130
 34  ω     40.00 105.00   0.50   15.00    --  111.50 -94.00 150.00  130
 35  ω     40.00  79.00   0.50   15.00    --  111.50 -61.00-120.00   78
 36  ω   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00 -90.00  186
 37  ω   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00-180.00  186
 38  ω   -120.00 -35.00   0.50    5.00    --  -48.54 -57.00-150.00  170
 39  ω   -120.00 -27.00   0.50    5.00    --  -48.54 -77.00  30.00  186
 40  ω     27.00 121.00   0.50    5.00    --   48.54  77.00 -30.00  188
 41  ω     35.00 121.00   0.50    5.00    --   48.54  57.00 -60.00  172
 42  ω     27.00 121.00   0.50    5.00    --   48.54  77.00  30.00  188
 43  ω     27.00 121.00   0.50    5.00    --   48.54  77.00 120.00  188
 44  ω   -161.00 -83.00   0.50   15.00    --  -90.00 -77.00-150.00  156
 45  ω   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00 -60.00  186
 46  ω   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00  30.00  186
 47  ω   -161.00 -68.00   0.50   15.00    --  -90.00 -77.00 163.06  186
 48  ω    101.00 178.00   0.50   15.00    --  111.50  30.00-150.00  154
 49  ω     31.00  57.00   0.50    5.00    --   48.54  77.00-180.00   52
 50  ω    -47.00 -22.00   0.50    5.00    --    2.00 130.00-141.19   50
 51  ω    -64.00 -39.00   0.50    5.00    --   10.00 167.00  -4.67   50
 52  ω     -4.00  21.00   0.50    5.00    --   26.00  95.00-146.78   50
 53  ω      4.00  29.00   0.50    5.00    --   34.00  95.00 -18.65   50
 54  ω     13.00  38.00   0.50    5.00    --   42.00  92.00  14.42   50
 55  ω     17.00  42.00   0.50    5.00    --   42.00  85.00  98.60   50
 56  ω    -60.00 -35.00   0.50    5.00    --  -48.54 -57.00 120.00   50
 57  ω    -52.00 -27.00   0.50    5.00    --  -48.54 -77.00-150.00   50
 58  ω   -114.00 -88.00   0.50    5.00    --  -48.54 -77.00-150.00   52
 59  ω     55.00  84.00   0.50    5.00    --   48.54  37.00   0.00   58
 60  ω     53.00  81.00   0.50    5.00    --   48.54  19.00-180.00   56
 61  ω    -62.00 -36.00   0.50    5.00    --  -58.00 -77.00 -65.53   52
 62  ω    -70.00 -44.00   0.50    5.00    --  -58.00 -57.00   4.95   52
 63  ω    -68.00 -42.00   0.50    5.00    --  -62.00 -72.00-132.26   52
 64  ω    -76.00 -50.00   0.50    5.00    --  -66.00 -67.00 151.75   52
 65  ω    -75.00 -49.00   0.50    5.00    --  -66.00 -68.00 -30.50   52
 66  ω    -76.00 -50.00   0.50    5.00    --  -66.00 -66.00   3.07   52
 67  ω     49.00  74.00   0.50    5.00    --   70.00  75.00 134.75   50
 68  ω     49.00  75.00   0.50    5.00    --   70.00  75.00  95.70   52
 69  ω    -79.00 -53.00   0.50   15.00    --  -70.00 -68.00 -86.39   52
 70  ω    -78.00 -52.00   0.50   15.00    --  -70.00 -67.00-176.10   52
 71  ω    -82.00 -57.00   0.50   15.00    --  -74.00 -65.00 -52.62   50
 72  ω    -84.00 -58.00   0.50   15.00    --  -78.00 -75.00 -14.03   52
 73  ω    -83.00 -57.00   0.50   15.00    --  -78.00 -74.00 143.52   52
 74  ω    -87.00 -62.00   0.50   15.00    --  -82.00 -73.00 105.42   50
 75  ω    -91.00 -65.00   0.50   15.00    --  -82.00 -66.00-141.78   52
 76  ω    -88.00 -62.00   0.50   15.00    --  -82.00 -72.00  74.90   52
 77  ω    -86.00 -60.00   0.50   15.00    --  -82.00 -77.00-131.34   52
 78  ω    -91.00 -65.00   0.50   15.00    --  -82.00 -68.00  33.18   52
 79  ω    -97.00 -71.00   0.50   15.00    --  -86.00 -61.00  49.22   52
 80  ω    -96.00 -71.00   0.50   15.00    --  -90.00 -70.00-132.58   50
 81  ω    -96.00 -70.00   0.50   15.00    --  -90.00 -77.00  90.00   52
 82  ω    -96.00 -70.00   0.50   15.00    --  -90.00 -77.00 -90.00   52
 83  ω    -95.00 -70.00   0.50   15.00    --  -90.00 -76.00 -82.09   50
 84  ω    -93.00 -68.00   0.50   15.00    --  -90.00 -77.00-150.00   50
 85  ω   -156.00-130.00   0.50   15.00    --  -90.00 -76.00 -82.09   52
 86  ω    -95.00 -69.00   0.50   15.00    --  -90.00 -77.00 150.00   52
 87  ω   -161.00-126.00   0.50   15.00    --  -90.00 -70.00-132.58   70
 88  ω    -98.00 -73.00   0.50   15.00    --  -90.00 -64.00 170.97   50
 89  ω    -95.00 -69.00   0.50   15.00    --  -90.00 -75.00  43.04   52
 90  ω   -102.00 -77.00   0.50   15.00    --  -90.00 -61.00 120.00   50
 91  ω    -97.00 -71.00   0.50   15.00    --  -90.00 -75.00 -15.97   52
 92  ω    -93.00 -68.00   0.50   15.00    --  -90.00 -77.00 -30.00   50
 93  ω   -100.00 -74.00   0.50   15.00    --  -90.00 -64.00  -3.09   52
 94  ω     91.00 117.00   0.50   15.00    --  111.50  77.00 -60.00   52
 95  ω    112.00 143.00   0.50   15.00    --  111.50  77.00-180.00   62
 96  ω     97.00 129.00   0.50   15.00    --  111.50  61.00 150.00   64
 97  ω    128.00 154.00   0.50   15.00    --  111.50  15.00   0.00   52
 98  ω     49.00  75.00   0.50   15.00    --  111.50-125.00  90.00   52
 99  ω    134.00 161.00   0.50   15.00    --  111.50  77.00   0.00   54
100  ω     48.00  74.00   0.50   15.00    --  111.50-125.00 -30.00   52
101  ω     90.00 116.00   0.50   15.00    --  111.50  77.00   0.00   52
102  ω     90.00 117.00   0.50   15.00    --  111.50  77.00-120.00   54
103  ω    121.00 147.00   0.50   15.00    --  111.50  77.00-150.00   52
104  ω    139.00 167.00   0.50   15.00    --  111.50  61.00  90.00   56
105  ω     99.00 129.00   0.50   15.00    --  111.50  61.00  90.00   60
106  ω     91.00 117.00   0.50   15.00    --  111.50  77.00-150.00   52
107  ω     93.00 119.00   0.50   15.00    --  111.50  77.00  90.00   52
108  ω    101.00 127.00   0.50   15.00    --  111.50  61.00   0.00   52
109  ω    130.00 156.00   0.50   15.00    --  111.50  77.00 150.00   52
110  ω     40.00  65.00   0.50   15.00    --  111.50 -61.00-180.00   50
111  ω     46.00  72.00   0.50   15.00    --  111.50-125.00  30.00   52
112  ω     95.00 122.00   0.50   15.00    --  111.50  77.00 150.00   54
113  ω     91.00 117.00   0.50   15.00    --  111.50  77.00  60.00   52
114  ω     93.00 118.00   0.50   15.00    --  111.50  77.00  30.00   50
115  ω    132.00 170.00   0.50   15.00    --  111.50  77.00 -90.00   76
116  ω    102.00 128.00   0.50   15.00    --  111.50  45.00   0.00   52
117  ω     94.00 127.00   0.50   15.00    --  111.50  77.00 -90.00   66
118  ω     98.00 151.00   0.50   15.00    --  111.50  61.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2126753000
_diffrn_orient_matrix_UB_12      0.0533806000
_diffrn_orient_matrix_UB_13      -0.0980584000
_diffrn_orient_matrix_UB_21      -0.1024930000
_diffrn_orient_matrix_UB_22      0.1448534000
_diffrn_orient_matrix_UB_23      0.0286851000
_diffrn_orient_matrix_UB_31      0.1907452000
_diffrn_orient_matrix_UB_32      0.0851242000
_diffrn_orient_matrix_UB_33      -0.0939037000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3764
_reflns_number_total             4253
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.145
_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)+(0.0606P)²+0.0162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(8)
 -0.1(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30)
;
_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
N1 N 0.7351(6) 0.9392(3) 0.2495(3) 0.0741(7) Uani 1 1 d . . . . .
N2 N 0.5090(4) 0.6389(2) 0.46849(17) 0.0507(4) Uani 1 1 d . . . . .
C1 C 0.7470(4) 0.5448(2) 0.31974(18) 0.0405(4) Uani 1 1 d . . . . .
C2 C 0.5554(4) 0.5760(2) 0.23179(19) 0.0425(4) Uani 1 1 d . . . . .
C3 C 0.3505(4) 0.7088(3) 0.1970(2) 0.0499(5) Uani 1 1 d . . . . .
H3 H 0.337459 0.778599 0.234701 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1752(5) 0.7342(3) 0.1097(2) 0.0586(6) Uani 1 1 d . . . . .
H4 H 0.046515 0.822581 0.087466 0.070 Uiso 1 1 calc R U . . .
C5 C 0.1834(5) 0.6299(4) 0.0519(2) 0.0637(7) Uani 1 1 d . . . . .
H5 H 0.062974 0.650441 -0.008628 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3664(5) 0.5003(3) 0.0846(2) 0.0589(6) Uani 1 1 d . . . . .
H6 H 0.367854 0.430501 0.047800 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5579(4) 0.4684(3) 0.17475(19) 0.0466(5) Uani 1 1 d . . . . .
C8 C 0.7453(5) 0.3341(3) 0.2090(2) 0.0510(5) Uani 1 1 d . . . . .
H8 H 0.744377 0.264354 0.172403 0.061 Uiso 1 1 calc R U . . .
C9 C 0.9335(4) 0.3012(2) 0.2962(2) 0.0461(5) Uani 1 1 d . . . . .
C10 C 1.1254(5) 0.1633(3) 0.3293(3) 0.0604(6) Uani 1 1 d . . . . .
H10 H 1.123827 0.094933 0.291436 0.072 Uiso 1 1 calc R U . . .
C11 C 1.3079(5) 0.1298(3) 0.4135(3) 0.0649(7) Uani 1 1 d . . . . .
H11 H 1.431208 0.039259 0.433408 0.078 Uiso 1 1 calc R U . . .
C12 C 1.3126(5) 0.2324(3) 0.4721(3) 0.0613(6) Uani 1 1 d . . . . .
H12 H 1.437970 0.207990 0.531333 0.074 Uiso 1 1 calc R U . . .
C13 C 1.1362(5) 0.3661(3) 0.4429(2) 0.0520(5) Uani 1 1 d . . . . .
H13 H 1.145104 0.432222 0.481937 0.062 Uiso 1 1 calc R U . . .
C14 C 0.9369(4) 0.4078(2) 0.35353(19) 0.0425(5) Uani 1 1 d . . . . .
C15 C 0.7397(4) 0.6523(2) 0.3869(2) 0.0451(5) Uani 1 1 d . . . . .
H15 H 0.899072 0.618247 0.436393 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7304(5) 0.8143(3) 0.3073(2) 0.0519(5) Uani 1 1 d . . . . .
C17 C 0.5600(4) 0.5525(3) 0.5760(2) 0.0489(5) Uani 1 1 d . . . . .
H17 H 0.736232 0.511274 0.596101 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3655(5) 0.5108(3) 0.67258(19) 0.0488(5) Uani 1 1 d . . . . .
C19 C 0.4180(5) 0.3590(3) 0.7599(2) 0.0558(6) Uani 1 1 d . . . . .
C20 C 0.6387(6) 0.2465(3) 0.7538(3) 0.0672(7) Uani 1 1 d . . . . .
H20 H 0.754706 0.271100 0.689246 0.081 Uiso 1 1 calc R U . . .
C21 C 0.6825(8) 0.1033(4) 0.8413(3) 0.0841(10) Uani 1 1 d . . . . .
H21 H 0.829752 0.032539 0.835984 0.101 Uiso 1 1 calc R U . . .
C22 C 0.5105(9) 0.0613(5) 0.9382(4) 0.0993(13) Uani 1 1 d . . . . .
H22 H 0.544434 -0.036494 0.997330 0.119 Uiso 1 1 calc R U . . .
C23 C 0.2941(8) 0.1626(5) 0.9465(3) 0.0907(11) Uani 1 1 d . . . . .
H23 H 0.178406 0.132756 1.010573 0.109 Uiso 1 1 calc R U . . .
C24 C 0.2402(6) 0.3144(3) 0.8586(2) 0.0647(7) Uani 1 1 d . . . . .
C25 C 0.0195(6) 0.4198(4) 0.8659(2) 0.0711(8) Uani 1 1 d . . . . .
H25 H -0.097110 0.389269 0.929469 0.085 Uiso 1 1 calc R U . . .
C26 C -0.0347(5) 0.5686(3) 0.7825(2) 0.0589(6) Uani 1 1 d . . . . .
C27 C -0.2621(6) 0.6763(4) 0.7917(3) 0.0748(8) Uani 1 1 d . . . . .
H27 H -0.380595 0.645298 0.854347 0.090 Uiso 1 1 calc R U . . .
C28 C -0.3083(6) 0.8206(4) 0.7123(3) 0.0756(8) Uani 1 1 d . . . . .
H28 H -0.457822 0.888397 0.719972 0.091 Uiso 1 1 calc R U . . .
C29 C -0.1310(6) 0.8697(4) 0.6174(3) 0.0731(8) Uani 1 1 d . . . . .
H29 H -0.162240 0.971027 0.564096 0.088 Uiso 1 1 calc R U . . .
C30 C 0.0847(5) 0.7725(3) 0.6018(2) 0.0587(6) Uani 1 1 d . . . . .
H30 H 0.197056 0.807769 0.537278 0.070 Uiso 1 1 calc R U . . .
C31 C 0.1423(4) 0.6165(3) 0.6830(2) 0.0514(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.140(3) . ?
N2 C15 1.481(3) . ?
N2 C17 1.255(3) . ?
C1 C2 1.410(3) . ?
C1 C14 1.415(3) . ?
C1 C15 1.524(3) . ?
C2 C3 1.432(3) . ?
C2 C7 1.436(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.348(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.427(3) . ?
C7 C8 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 C10 1.427(3) . ?
C9 C14 1.436(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.339(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.414(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.358(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.432(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.480(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.467(3) . ?
C18 C19 1.424(3) . ?
C18 C31 1.409(3) . ?
C19 C20 1.425(4) . ?
C19 C24 1.429(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.393(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.354(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.427(4) . ?
C24 C25 1.388(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.387(4) . ?
C26 C27 1.431(4) . ?
C26 C31 1.437(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.337(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.404(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.356(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.430(4) . ?

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
C17 N2 C15 114.73(19) . . ?
C2 C1 C14 120.61(17) . . ?
C2 C1 C15 120.41(18) . . ?
C14 C1 C15 118.82(18) . . ?
C1 C2 C3 123.65(18) . . ?
C1 C2 C7 119.27(18) . . ?
C3 C2 C7 117.05(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 119.5(2) . . ?
C8 C7 C2 119.50(18) . . ?
C8 C7 C6 121.0(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 121.91(18) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 121.02(19) . . ?
C8 C9 C14 119.61(18) . . ?
C10 C9 C14 119.4(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.7(2) . . ?
C14 C13 H13 119.1 . . ?
C1 C14 C9 119.09(18) . . ?
C1 C14 C13 124.37(18) . . ?
C13 C14 C9 116.54(18) . . ?
N2 C15 C1 108.61(17) . . ?
N2 C15 H15 108.0 . . ?
C1 C15 H15 108.0 . . ?
C16 C15 N2 109.85(17) . . ?
C16 C15 C1 114.07(18) . . ?
C16 C15 H15 108.0 . . ?
N1 C16 C15 176.1(3) . . ?
N2 C17 H17 117.2 . . ?
N2 C17 C18 125.6(2) . . ?
C18 C17 H17 117.2 . . ?
C19 C18 C17 116.8(2) . . ?
C31 C18 C17 122.3(2) . . ?
C31 C18 C19 120.8(2) . . ?
C18 C19 C20 123.5(2) . . ?
C18 C19 C24 119.1(2) . . ?
C20 C19 C24 117.5(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(4) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.2(3) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C19 119.0(3) . . ?
C25 C24 C19 119.1(2) . . ?
C25 C24 C23 121.9(3) . . ?
C24 C25 H25 118.6 . . ?
C26 C25 C24 122.9(3) . . ?
C26 C25 H25 118.6 . . ?
C25 C26 C27 122.3(3) . . ?
C25 C26 C31 119.1(2) . . ?
C27 C26 C31 118.7(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.6(3) . . ?
C28 C27 H27 119.2 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 119.5 . . ?
C29 C30 C31 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C18 C31 C26 119.1(2) . . ?
C18 C31 C30 123.6(2) . . ?
C30 C31 C26 117.2(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
N2 C17 C18 C19 144.0(2) . . . . ?
N2 C17 C18 C31 -38.8(3) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C7 C6 -179.2(2) . . . . ?
C1 C2 C7 C8 1.4(3) . . . . ?
C2 C1 C14 C9 0.5(3) . . . . ?
C2 C1 C14 C13 -179.2(2) . . . . ?
C2 C1 C15 N2 69.7(2) . . . . ?
C2 C1 C15 C16 -53.2(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C2 C7 C8 C9 -0.8(3) . . . . ?
C3 C2 C7 C6 2.2(3) . . . . ?
C3 C2 C7 C8 -177.2(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C7 -1.8(4) . . . . ?
C5 C6 C7 C2 0.1(4) . . . . ?
C5 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C9 179.8(2) . . . . ?
C7 C2 C3 C4 -3.0(3) . . . . ?
C7 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C14 0.1(3) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C8 C9 C14 C1 0.1(3) . . . . ?
C8 C9 C14 C13 179.8(2) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C9 C14 C1 179.6(2) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C1 179.6(2) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C14 C1 C2 C3 177.2(2) . . . . ?
C14 C1 C2 C7 -1.3(3) . . . . ?
C14 C1 C15 N2 -105.6(2) . . . . ?
C14 C1 C15 C16 131.5(2) . . . . ?
C14 C9 C10 C11 0.6(4) . . . . ?
C15 N2 C17 C18 -175.3(2) . . . . ?
C15 C1 C2 C3 1.9(3) . . . . ?
C15 C1 C2 C7 -176.49(19) . . . . ?
C15 C1 C14 C9 175.85(19) . . . . ?
C15 C1 C14 C13 -3.9(3) . . . . ?
C17 N2 C15 C1 98.3(2) . . . . ?
C17 N2 C15 C16 -136.3(2) . . . . ?
C17 C18 C19 C20 -3.3(3) . . . . ?
C17 C18 C19 C24 177.51(19) . . . . ?
C17 C18 C31 C26 -177.86(19) . . . . ?
C17 C18 C31 C30 -0.2(3) . . . . ?
C18 C19 C20 C21 178.8(2) . . . . ?
C18 C19 C24 C23 -179.6(2) . . . . ?
C18 C19 C24 C25 0.8(3) . . . . ?
C19 C18 C31 C26 -0.7(3) . . . . ?
C19 C18 C31 C30 176.9(2) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C19 C24 C25 C26 -1.3(4) . . . . ?
C20 C19 C24 C23 1.3(3) . . . . ?
C20 C19 C24 C25 -178.4(2) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C22 C23 C24 C19 0.5(5) . . . . ?
C22 C23 C24 C25 -179.9(3) . . . . ?
C23 C24 C25 C26 179.0(2) . . . . ?
C24 C19 C20 C21 -2.1(4) . . . . ?
C24 C25 C26 C27 -179.5(2) . . . . ?
C24 C25 C26 C31 0.8(4) . . . . ?
C25 C26 C27 C28 178.3(2) . . . . ?
C25 C26 C31 C18 0.2(3) . . . . ?
C25 C26 C31 C30 -177.6(2) . . . . ?
C26 C27 C28 C29 -0.3(5) . . . . ?
C27 C26 C31 C18 -179.4(2) . . . . ?
C27 C26 C31 C30 2.7(3) . . . . ?
C27 C28 C29 C30 1.9(5) . . . . ?
C28 C29 C30 C31 -1.1(4) . . . . ?
C29 C30 C31 C18 -178.9(2) . . . . ?
C29 C30 C31 C26 -1.2(3) . . . . ?
C31 C18 C19 C20 179.4(2) . . . . ?
C31 C18 C19 C24 0.2(3) . . . . ?
C31 C26 C27 C28 -2.1(4) . . . . ?

_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 5.113
_oxdiff_exptl_absorpt_empirical_full_min 0.485
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(8)
2 -0.1(8)

