# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wjg10cult
_database_code_depnum_ccdc_archive 'CCDC 2085870'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H13 N'
_chemical_formula_sum            'C18 H13 N'
_chemical_formula_weight         243.29
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.2558(8)
_cell_length_b                   10.8126(4)
_cell_length_c                   17.9094(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.874(7)
_cell_angle_gamma                90
_cell_volume                     2543.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.0800
_cell_measurement_theta_min      5.0890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7642
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_min         5.103
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00 108.00   1.00    5.00    --  110.57 -94.00  60.00   81
  2  ω     -9.00  36.00   1.00    2.00    --  -40.45  37.00  90.00   45
  3  ω    -66.00 -22.00   1.00    2.00    --  -40.45  37.00  90.00   44
  4  ω    -65.00  36.00   1.00    2.00    --  -40.45  37.00-120.00  101
  5  ω     35.00  63.00   1.00    2.00    --   40.45-125.00 150.00   28
  6  ω     36.00 122.00   1.00    5.00    --  110.57-125.00 -90.00   86
  7  ω     83.00 178.00   1.00    5.00    --  110.57  45.00  30.00   95
  8  ω     80.00 178.00   1.00    5.00    --  110.57  61.00 120.00   98
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1122940000
_diffrn_orient_matrix_UB_12      0.0313217000
_diffrn_orient_matrix_UB_13      0.0505976000
_diffrn_orient_matrix_UB_21      -0.0332447000
_diffrn_orient_matrix_UB_22      0.1159810000
_diffrn_orient_matrix_UB_23      0.0333588000
_diffrn_orient_matrix_UB_31      -0.0046702000
_diffrn_orient_matrix_UB_32      -0.0766746000
_diffrn_orient_matrix_UB_33      0.0709802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3128
_reflns_number_total             4525
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.004
_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)+(0.0210P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
  C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C22A(H22A), C23A(H23A),
 C24A(H24A), C25A(H25A), C26A(H26A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.16193(13) 0.07833(16) 0.43750(10) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.12824(15) -0.02615(19) 0.46530(12) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.12508(15) -0.04729(19) 0.54115(12) 0.0228(4) Uani 1 1 d . . . . .
H2 H 0.1482 0.0132 0.5828 0.027 Uiso 1 1 calc R . . . .
C3 C 0.08711(16) -0.1592(2) 0.55333(12) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.0843 -0.1759 0.6045 0.031 Uiso 1 1 calc R . . . .
C4 C 0.05261(17) -0.2490(2) 0.49230(13) 0.0292(5) Uani 1 1 d . . . . .
H4 H 0.0280 -0.3260 0.5028 0.035 Uiso 1 1 calc R . . . .
C5 C 0.05419(16) -0.22641(19) 0.41667(13) 0.0261(5) Uani 1 1 d . . . . .
H5 H 0.0295 -0.2867 0.3749 0.031 Uiso 1 1 calc R . . . .
C6 C 0.09243(15) -0.11403(19) 0.40261(12) 0.0214(4) Uani 1 1 d . . . . .
C7 C 0.10372(15) -0.05985(19) 0.33273(12) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.08102(16) -0.0999(2) 0.25341(12) 0.0261(5) Uani 1 1 d . . . . .
H8 H 0.0510 -0.1787 0.2361 0.031 Uiso 1 1 calc R . . . .
C9 C 0.10285(17) -0.0234(2) 0.20060(12) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.0870 -0.0498 0.1464 0.034 Uiso 1 1 calc R . . . .
C10 C 0.14796(16) 0.0923(2) 0.22563(12) 0.0274(5) Uani 1 1 d . . . . .
H10 H 0.1635 0.1425 0.1884 0.033 Uiso 1 1 calc R . . . .
C11 C 0.17051(16) 0.1353(2) 0.30376(12) 0.0262(5) Uani 1 1 d . . . . .
H11 H 0.2007 0.2142 0.3206 0.031 Uiso 1 1 calc R . . . .
C12 C 0.14702(15) 0.05811(19) 0.35641(12) 0.0224(4) Uani 1 1 d . . . . .
C21 C 0.20437(16) 0.18612(19) 0.48408(12) 0.0228(4) Uani 1 1 d . . . . .
C22 C 0.28530(16) 0.1746(2) 0.55814(12) 0.0253(4) Uani 1 1 d . . . . .
H22 H 0.3130 0.0953 0.5772 0.030 Uiso 1 1 calc R . . . .
C23 C 0.32585(18) 0.2793(2) 0.60450(13) 0.0331(5) Uani 1 1 d . . . . .
H23 H 0.3814 0.2716 0.6554 0.040 Uiso 1 1 calc R . . . .
C24 C 0.28556(19) 0.3942(2) 0.57672(14) 0.0367(6) Uani 1 1 d . . . . .
H24 H 0.3127 0.4656 0.6088 0.044 Uiso 1 1 calc R . . . .
C25 C 0.20556(19) 0.4056(2) 0.50205(15) 0.0358(5) Uani 1 1 d . . . . .
H25 H 0.1790 0.4852 0.4827 0.043 Uiso 1 1 calc R . . . .
C26 C 0.16380(17) 0.30196(19) 0.45528(13) 0.0271(5) Uani 1 1 d . . . . .
H26 H 0.1084 0.3099 0.4044 0.033 Uiso 1 1 calc R . . . .
N1A N 0.44338(12) 0.40765(16) 0.34162(9) 0.0216(4) Uani 1 1 d . . . . .
C1A C 0.50188(15) 0.41642(19) 0.29520(11) 0.0205(4) Uani 1 1 d . . . . .
C2A C 0.48950(15) 0.49637(19) 0.23074(12) 0.0233(4) Uani 1 1 d . . . . .
H2A H 0.4349 0.5539 0.2119 0.028 Uiso 1 1 calc R . . . .
C3A C 0.56031(16) 0.48820(19) 0.19551(12) 0.0240(4) Uani 1 1 d . . . . .
H3A H 0.5544 0.5417 0.1518 0.029 Uiso 1 1 calc R . . . .
C4A C 0.64050(16) 0.4028(2) 0.22281(12) 0.0252(4) Uani 1 1 d . . . . .
H4A H 0.6868 0.3980 0.1965 0.030 Uiso 1 1 calc R . . . .
C5A C 0.65304(15) 0.32546(19) 0.28740(11) 0.0234(4) Uani 1 1 d . . . . .
H5A H 0.7081 0.2685 0.3060 0.028 Uiso 1 1 calc R . . . .
C6A C 0.58395(15) 0.33202(18) 0.32499(11) 0.0193(4) Uani 1 1 d . . . . .
C7A C 0.57445(15) 0.27040(18) 0.39327(11) 0.0201(4) Uani 1 1 d . . . . .
C8A C 0.63212(16) 0.18051(18) 0.44731(12) 0.0230(4) Uani 1 1 d . . . . .
H8A H 0.6930 0.1499 0.4443 0.028 Uiso 1 1 calc R . . . .
C9A C 0.59894(16) 0.13653(19) 0.50550(12) 0.0257(5) Uani 1 1 d . . . . .
H9A H 0.6376 0.0752 0.5428 0.031 Uiso 1 1 calc R . . . .
C10A C 0.50911(16) 0.1814(2) 0.51003(12) 0.0261(5) Uani 1 1 d . . . . .
H10A H 0.4872 0.1485 0.5498 0.031 Uiso 1 1 calc R . . . .
C11A C 0.45145(16) 0.27233(19) 0.45809(11) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.3909 0.3031 0.4616 0.028 Uiso 1 1 calc R . . . .
C12A C 0.48617(15) 0.31683(19) 0.40026(11) 0.0207(4) Uani 1 1 d . . . . .
C21A C 0.34675(15) 0.46434(18) 0.32382(11) 0.0205(4) Uani 1 1 d . . . . .
C22A C 0.33732(17) 0.5613(2) 0.37120(13) 0.0307(5) Uani 1 1 d . . . . .
H22A H 0.3955 0.5922 0.4146 0.037 Uiso 1 1 calc R . . . .
C23A C 0.24228(17) 0.6126(2) 0.35460(14) 0.0339(5) Uani 1 1 d . . . . .
H23A H 0.2355 0.6795 0.3865 0.041 Uiso 1 1 calc R . . . .
C24A C 0.15678(16) 0.5669(2) 0.29167(13) 0.0275(5) Uani 1 1 d . . . . .
H24A H 0.0915 0.6011 0.2813 0.033 Uiso 1 1 calc R . . . .
C25A C 0.16752(16) 0.4711(2) 0.24427(12) 0.0265(5) Uani 1 1 d . . . . .
H25A H 0.1095 0.4403 0.2007 0.032 Uiso 1 1 calc R . . . .
C26A C 0.26255(16) 0.4200(2) 0.26000(12) 0.0245(4) Uani 1 1 d . . . . .
H26A H 0.2697 0.3548 0.2270 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.393(3) . ?
N1 C12 1.401(2) . ?
N1 C21 1.424(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.446(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.409(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.394(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.392(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.378(4) . ?
C24 C25 1.385(3) . ?
C25 C26 1.387(3) . ?
N1A C1A 1.391(3) . ?
N1A C12A 1.393(3) . ?
N1A C21A 1.426(2) . ?
C1A C2A 1.397(3) . ?
C1A C6A 1.414(3) . ?
C2A C3A 1.385(3) . ?
C3A C4A 1.402(3) . ?
C4A C5A 1.381(3) . ?
C5A C6A 1.394(3) . ?
C6A C7A 1.444(3) . ?
C7A C8A 1.392(3) . ?
C7A C12A 1.405(3) . ?
C8A C9A 1.385(3) . ?
C9A C10A 1.401(3) . ?
C10A C11A 1.383(3) . ?
C11A C12A 1.396(3) . ?
C21A C22A 1.388(3) . ?
C21A C26A 1.382(3) . ?
C22A C23A 1.385(3) . ?
C23A C24A 1.390(3) . ?
C24A C25A 1.385(3) . ?
C25A C26A 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.03(17) . . ?
C1 N1 C21 125.54(17) . . ?
C12 N1 C21 126.42(18) . . ?
N1 C1 C2 128.82(19) . . ?
N1 C1 C6 109.34(17) . . ?
C2 C1 C6 121.82(19) . . ?
C3 C2 C1 117.49(19) . . ?
C2 C3 C4 121.74(19) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 119.12(19) . . ?
C1 C6 C7 106.80(18) . . ?
C5 C6 C1 119.38(19) . . ?
C5 C6 C7 133.80(19) . . ?
C8 C7 C6 134.0(2) . . ?
C8 C7 C12 119.2(2) . . ?
C12 C7 C6 106.82(17) . . ?
C9 C8 C7 119.1(2) . . ?
C8 C9 C10 121.0(2) . . ?
C11 C10 C9 121.4(2) . . ?
C10 C11 C12 117.3(2) . . ?
N1 C12 C7 109.00(18) . . ?
C11 C12 N1 128.91(19) . . ?
C11 C12 C7 122.08(19) . . ?
C22 C21 N1 119.57(19) . . ?
C22 C21 C26 120.5(2) . . ?
C26 C21 N1 119.92(19) . . ?
C21 C22 C23 119.8(2) . . ?
C24 C23 C22 120.0(2) . . ?
C23 C24 C25 120.0(2) . . ?
C24 C25 C26 120.6(2) . . ?
C25 C26 C21 119.0(2) . . ?
C1A N1A C12A 108.07(16) . . ?
C1A N1A C21A 126.06(16) . . ?
C12A N1A C21A 124.97(17) . . ?
N1A C1A C2A 128.57(19) . . ?
N1A C1A C6A 109.31(17) . . ?
C2A C1A C6A 122.08(19) . . ?
C3A C2A C1A 117.15(19) . . ?
C2A C3A C4A 121.54(19) . . ?
C5A C4A C3A 120.89(19) . . ?
C4A C5A C6A 119.20(19) . . ?
C1A C6A C7A 106.32(17) . . ?
C5A C6A C1A 119.12(18) . . ?
C5A C6A C7A 134.56(19) . . ?
C8A C7A C6A 133.32(19) . . ?
C8A C7A C12A 119.66(19) . . ?
C12A C7A C6A 107.02(17) . . ?
C9A C8A C7A 118.72(19) . . ?
C8A C9A C10A 120.79(19) . . ?
C11A C10A C9A 121.66(19) . . ?
C10A C11A C12A 117.05(19) . . ?
N1A C12A C7A 109.24(17) . . ?
N1A C12A C11A 128.67(19) . . ?
C11A C12A C7A 122.09(19) . . ?
C22A C21A N1A 120.18(18) . . ?
C26A C21A N1A 119.26(18) . . ?
C26A C21A C22A 120.5(2) . . ?
C23A C22A C21A 119.4(2) . . ?
C22A C23A C24A 120.6(2) . . ?
C25A C24A C23A 119.4(2) . . ?
C24A C25A C26A 120.4(2) . . ?
C21A C26A C25A 119.71(19) . . ?

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
N1 C1 C2 C3 179.4(2) . . . . ?
N1 C1 C6 C5 -179.63(18) . . . . ?
N1 C1 C6 C7 -0.7(2) . . . . ?
N1 C21 C22 C23 -178.87(19) . . . . ?
N1 C21 C26 C25 179.3(2) . . . . ?
C1 N1 C12 C7 0.0(2) . . . . ?
C1 N1 C12 C11 -178.9(2) . . . . ?
C1 N1 C21 C22 52.8(3) . . . . ?
C1 N1 C21 C26 -126.6(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 C8 -179.1(2) . . . . ?
C1 C6 C7 C12 0.7(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 177.84(18) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C12 179.4(2) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C6 C7 C12 N1 -0.4(2) . . . . ?
C6 C7 C12 C11 178.55(19) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C7 C12 N1 179.38(18) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 N1 179.7(2) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C12 N1 C1 C2 -177.9(2) . . . . ?
C12 N1 C1 C6 0.5(2) . . . . ?
C12 N1 C21 C22 -126.9(2) . . . . ?
C12 N1 C21 C26 53.6(3) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C21 N1 C1 C2 2.3(3) . . . . ?
C21 N1 C1 C6 -179.30(19) . . . . ?
C21 N1 C12 C7 179.72(19) . . . . ?
C21 N1 C12 C11 0.9(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.9(4) . . . . ?
C23 C24 C25 C26 1.3(4) . . . . ?
C24 C25 C26 C21 -0.8(3) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
N1A C1A C2A C3A 178.55(19) . . . . ?
N1A C1A C6A C5A -179.77(17) . . . . ?
N1A C1A C6A C7A -0.5(2) . . . . ?
N1A C21A C22A C23A -177.9(2) . . . . ?
N1A C21A C26A C25A 177.34(18) . . . . ?
C1A N1A C12A C7A 2.1(2) . . . . ?
C1A N1A C12A C11A -177.1(2) . . . . ?
C1A N1A C21A C22A -110.2(2) . . . . ?
C1A N1A C21A C26A 71.1(3) . . . . ?
C1A C2A C3A C4A 0.5(3) . . . . ?
C1A C6A C7A C8A -179.0(2) . . . . ?
C1A C6A C7A C12A 1.8(2) . . . . ?
C2A C1A C6A C5A -2.0(3) . . . . ?
C2A C1A C6A C7A 177.21(18) . . . . ?
C2A C3A C4A C5A -1.6(3) . . . . ?
C3A C4A C5A C6A 0.8(3) . . . . ?
C4A C5A C6A C1A 0.9(3) . . . . ?
C4A C5A C6A C7A -178.0(2) . . . . ?
C5A C6A C7A C8A 0.1(4) . . . . ?
C5A C6A C7A C12A -179.1(2) . . . . ?
C6A C1A C2A C3A 1.3(3) . . . . ?
C6A C7A C8A C9A -177.3(2) . . . . ?
C6A C7A C12A N1A -2.4(2) . . . . ?
C6A C7A C12A C11A 176.81(18) . . . . ?
C7A C8A C9A C10A 0.0(3) . . . . ?
C8A C7A C12A N1A 178.22(17) . . . . ?
C8A C7A C12A C11A -2.5(3) . . . . ?
C8A C9A C10A C11A -1.3(3) . . . . ?
C9A C10A C11A C12A 0.6(3) . . . . ?
C10A C11A C12A N1A -179.62(19) . . . . ?
C10A C11A C12A C7A 1.3(3) . . . . ?
C12A N1A C1A C2A -178.51(19) . . . . ?
C12A N1A C1A C6A -1.0(2) . . . . ?
C12A N1A C21A C22A 82.0(3) . . . . ?
C12A N1A C21A C26A -96.7(2) . . . . ?
C12A C7A C8A C9A 1.8(3) . . . . ?
C21A N1A C1A C2A 12.0(3) . . . . ?
C21A N1A C1A C6A -170.48(18) . . . . ?
C21A N1A C12A C7A 171.79(17) . . . . ?
C21A N1A C12A C11A -7.4(3) . . . . ?
C21A C22A C23A C24A 0.6(4) . . . . ?
C22A C21A C26A C25A -1.4(3) . . . . ?
C22A C23A C24A C25A -1.4(3) . . . . ?
C23A C24A C25A C26A 0.8(3) . . . . ?
C24A C25A C26A C21A 0.6(3) . . . . ?
C26A C21A C22A C23A 0.8(3) . . . . ?

_olex2_date_sample_data_collection 2017-07-04
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_wjg8cult
_database_code_depnum_ccdc_archive 'CCDC 2085873'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Br N'
_chemical_formula_sum            'C18 H12 Br N'
_chemical_formula_weight         322.20
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.42117(15)
_cell_length_b                   20.1472(4)
_cell_length_c                   8.63599(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.529(2)
_cell_angle_gamma                90
_cell_volume                     1389.26(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3297
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      75.3650
_cell_measurement_theta_min      5.3740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4009
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.389
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_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     33.00 107.00   1.00    2.00    --  110.57 -30.00-150.00   74
  2  ω      9.00  52.00   1.00    1.00    --   40.57 -99.00   0.00   43
  3  ω    -65.00  14.00   1.00    1.00    --  -40.57  57.00 -90.00   79
  4  ω   -112.00 -18.00   1.00    1.00    --  -40.57 -37.00  90.00   94
  5  ω     90.00 178.00   1.00    2.00    --  110.57  45.00-120.00   88
  6  ω    102.00 178.00   1.00    2.00    --  110.57 111.00 -90.00   76
  7  ω     80.00 178.00   1.00    2.00    --  110.57  77.00 -30.00   98
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0836859000
_diffrn_orient_matrix_UB_12      -0.0549719000
_diffrn_orient_matrix_UB_13      0.0709281000
_diffrn_orient_matrix_UB_21      -0.1738250000
_diffrn_orient_matrix_UB_22      0.0258386000
_diffrn_orient_matrix_UB_23      -0.1022786000
_diffrn_orient_matrix_UB_31      0.0023140000
_diffrn_orient_matrix_UB_32      -0.0464689000
_diffrn_orient_matrix_UB_33      -0.1410148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2377
_reflns_number_total             2449
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+1.3270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0863
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C22(H22),
 C23(H23), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84647(3) -0.03631(2) 0.09395(3) 0.02545(12) Uani 1 1 d . . . . .
N1 N 0.5118(2) 0.12333(9) 0.5004(2) 0.0137(4) Uani 1 1 d . . . . .
C1 C 0.3420(3) 0.13787(10) 0.4616(3) 0.0138(4) Uani 1 1 d . . . . .
C2 C 0.2098(3) 0.12055(11) 0.3220(3) 0.0163(4) Uani 1 1 d . . . . .
H2 H 0.2291 0.0979 0.2331 0.020 Uiso 1 1 calc R . . . .
C3 C 0.0498(3) 0.13776(11) 0.3190(3) 0.0185(5) Uani 1 1 d . . . . .
H3 H -0.0425 0.1261 0.2266 0.022 Uiso 1 1 calc R . . . .
C4 C 0.0201(3) 0.17183(11) 0.4478(3) 0.0208(5) Uani 1 1 d . . . . .
H4 H -0.0914 0.1831 0.4412 0.025 Uiso 1 1 calc R . . . .
C5 C 0.1513(3) 0.18948(11) 0.5854(3) 0.0189(5) Uani 1 1 d . . . . .
H5 H 0.1308 0.2128 0.6728 0.023 Uiso 1 1 calc R . . . .
C6 C 0.3144(3) 0.17215(10) 0.5927(3) 0.0148(4) Uani 1 1 d . . . . .
C7 C 0.4761(3) 0.17903(10) 0.7175(3) 0.0143(4) Uani 1 1 d . . . . .
C8 C 0.5295(3) 0.20913(10) 0.8710(3) 0.0181(5) Uani 1 1 d . . . . .
H8 H 0.4513 0.2302 0.9136 0.022 Uiso 1 1 calc R . . . .
C9 C 0.6980(3) 0.20783(11) 0.9601(3) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.7357 0.2279 1.0650 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8140(3) 0.17710(11) 0.8969(3) 0.0191(5) Uani 1 1 d . . . . .
H10 H 0.9293 0.1772 0.9597 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7641(3) 0.14671(10) 0.7451(3) 0.0162(4) Uani 1 1 d . . . . .
H11 H 0.8430 0.1258 0.7032 0.019 Uiso 1 1 calc R . . . .
C12 C 0.5940(3) 0.14796(10) 0.6560(3) 0.0134(4) Uani 1 1 d . . . . .
C21 C 0.5870(2) 0.08543(10) 0.4036(3) 0.0132(4) Uani 1 1 d . . . . .
C22 C 0.6931(3) 0.03273(10) 0.4739(3) 0.0148(4) Uani 1 1 d . . . . .
H22 H 0.7128 0.0218 0.5854 0.018 Uiso 1 1 calc R . . . .
C23 C 0.7698(3) -0.00371(10) 0.3813(3) 0.0153(4) Uani 1 1 d . . . . .
H23 H 0.8448 -0.0387 0.4293 0.018 Uiso 1 1 calc R . . . .
C24 C 0.7353(3) 0.01183(11) 0.2179(3) 0.0161(4) Uani 1 1 d . . . . .
C25 C 0.6279(3) 0.06310(11) 0.1446(3) 0.0161(4) Uani 1 1 d . . . . .
H25 H 0.6039 0.0722 0.0315 0.019 Uiso 1 1 calc R . . . .
C26 C 0.5561(3) 0.10090(11) 0.2391(3) 0.0153(4) Uani 1 1 d . . . . .
H26 H 0.4858 0.1373 0.1918 0.018 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C24 1.897(2) . ?
N1 C1 1.391(3) . ?
N1 C12 1.393(3) . ?
N1 C21 1.422(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.396(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.399(3) . ?
C6 C7 1.450(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.412(3) . ?
C8 C9 1.383(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.394(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.383(3) . ?
C24 C25 1.386(3) . ?
C25 C26 1.388(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.37(18) . . ?
C1 N1 C21 125.94(18) . . ?
C12 N1 C21 125.53(18) . . ?
N1 C1 C2 129.0(2) . . ?
N1 C1 C6 109.24(19) . . ?
C2 C1 C6 121.7(2) . . ?
C3 C2 C1 117.2(2) . . ?
C2 C3 C4 121.9(2) . . ?
C5 C4 C3 120.9(2) . . ?
C4 C5 C6 118.5(2) . . ?
C1 C6 C7 106.76(19) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 133.3(2) . . ?
C8 C7 C6 133.7(2) . . ?
C8 C7 C12 119.8(2) . . ?
C12 C7 C6 106.54(19) . . ?
C9 C8 C7 118.9(2) . . ?
C8 C9 C10 120.6(2) . . ?
C11 C10 C9 121.6(2) . . ?
C10 C11 C12 117.6(2) . . ?
N1 C12 C7 109.09(19) . . ?
N1 C12 C11 129.4(2) . . ?
C11 C12 C7 121.5(2) . . ?
C22 C21 N1 119.7(2) . . ?
C26 C21 N1 120.33(19) . . ?
C26 C21 C22 119.9(2) . . ?
C23 C22 C21 120.2(2) . . ?
C24 C23 C22 118.9(2) . . ?
C23 C24 Br1 118.58(17) . . ?
C23 C24 C25 122.0(2) . . ?
C25 C24 Br1 119.38(17) . . ?
C24 C25 C26 118.9(2) . . ?
C25 C26 C21 120.0(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 C24 C25 C26 -175.67(16) . . . . ?
N1 C1 C2 C3 175.8(2) . . . . ?
N1 C1 C6 C5 -177.00(19) . . . . ?
N1 C1 C6 C7 0.2(2) . . . . ?
N1 C21 C22 C23 -178.68(19) . . . . ?
N1 C21 C26 C25 -179.05(19) . . . . ?
C1 N1 C12 C7 -0.4(2) . . . . ?
C1 N1 C12 C11 -178.4(2) . . . . ?
C1 N1 C21 C22 -128.8(2) . . . . ?
C1 N1 C21 C26 51.6(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C6 C7 C8 178.3(2) . . . . ?
C1 C6 C7 C12 -0.5(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 177.51(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -176.1(2) . . . . ?
C5 C6 C7 C8 -5.0(4) . . . . ?
C5 C6 C7 C12 176.2(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C7 C8 C9 -178.6(2) . . . . ?
C6 C7 C12 N1 0.5(2) . . . . ?
C6 C7 C12 C11 178.72(19) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C7 C12 N1 -178.46(18) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 N1 177.9(2) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C12 N1 C1 C2 -176.9(2) . . . . ?
C12 N1 C1 C6 0.1(2) . . . . ?
C12 N1 C21 C22 46.1(3) . . . . ?
C12 N1 C21 C26 -133.5(2) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C21 N1 C1 C2 -1.3(3) . . . . ?
C21 N1 C1 C6 175.66(19) . . . . ?
C21 N1 C12 C7 -175.99(18) . . . . ?
C21 N1 C12 C11 6.0(3) . . . . ?
C21 C22 C23 C24 -1.9(3) . . . . ?
C22 C21 C26 C25 1.3(3) . . . . ?
C22 C23 C24 Br1 177.93(16) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 1.5(3) . . . . ?
C24 C25 C26 C21 -2.5(3) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?

_olex2_date_sample_data_collection 2017-05-05
_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.600
####################################################################### 
# 
# 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_wjg6cult
_database_code_depnum_ccdc_archive 'CCDC 2085874'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H11 Br N2'
_chemical_formula_sum            'C17 H11 Br N2'
_chemical_formula_weight         323.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N Br H8'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6198(2)
_cell_length_b                   7.12537(14)
_cell_length_c                   16.4875(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.047(2)
_cell_angle_gamma                90
_cell_volume                     1335.03(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4510
_cell_measurement_theta_min      3.8770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3890
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.459
_diffrn_reflns_theta_min         3.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  34.00   1.00    1.00    --  -40.45  37.00  60.00  101
  2  ω      2.00  73.00   1.00    1.00    --   40.45 -99.00 150.00   71
  3  ω     30.00  93.00   1.00    1.00    --   40.45-125.00  30.00   63
  4  ω     33.00 138.00   1.00    3.00    --  110.57 -30.00-180.00  105
  5  ω     70.00 142.00   1.00    3.00    --  110.57 -77.00-180.00   72
  6  ω     92.00 177.00   1.00    3.00    --  110.57  77.00-180.00   85
  7  ω     95.00 178.00   1.00    3.00    --  110.57 125.00 -90.00   83
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438334000
_diffrn_orient_matrix_UB_12      0.1086679000
_diffrn_orient_matrix_UB_13      0.0685092000
_diffrn_orient_matrix_UB_21      0.0651065000
_diffrn_orient_matrix_UB_22      0.1769968000
_diffrn_orient_matrix_UB_23      -0.0203747000
_diffrn_orient_matrix_UB_31      -0.1102606000
_diffrn_orient_matrix_UB_32      0.0603916000
_diffrn_orient_matrix_UB_33      -0.0635158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2231
_reflns_number_total             2359
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0802
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C22(H22),
 C23(H23), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89529(2) 0.59989(2) 0.43013(2) 0.01928(12) Uani 1 1 d . . . . .
N1 N 0.40727(13) 0.5630(2) 0.22101(9) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.53770(13) 0.6358(2) 0.34439(10) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.30741(15) 0.5194(2) 0.25264(11) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.29908(16) 0.4639(3) 0.33233(12) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.3667 0.4590 0.3761 0.023 Uiso 1 1 calc R . . . .
C3 C 0.18825(19) 0.4161(3) 0.34543(13) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.1803 0.3765 0.3990 0.030 Uiso 1 1 calc R . . . .
C4 C 0.08828(18) 0.4251(3) 0.28140(14) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.0138 0.3915 0.2921 0.031 Uiso 1 1 calc R . . . .
C5 C 0.09659(15) 0.4826(3) 0.20251(13) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.0284 0.4903 0.1593 0.027 Uiso 1 1 calc R . . . .
C6 C 0.20778(15) 0.5291(2) 0.18771(12) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.24707(17) 0.5819(2) 0.11378(13) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.18886(18) 0.6137(2) 0.03195(13) 0.0214(4) Uani 1 1 d . . . . .
H8 H 0.1059 0.5997 0.0163 0.026 Uiso 1 1 calc R . . . .
C9 C 0.25299(17) 0.6657(3) -0.02611(12) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.2141 0.6859 -0.0821 0.029 Uiso 1 1 calc R . . . .
C10 C 0.37547(17) 0.6888(3) -0.00274(12) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.4180 0.7277 -0.0431 0.027 Uiso 1 1 calc R . . . .
C11 C 0.43573(16) 0.6562(3) 0.07783(12) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.5187 0.6707 0.0929 0.023 Uiso 1 1 calc R . . . .
C12 C 0.37096(17) 0.6017(2) 0.13625(12) 0.0160(4) Uani 1 1 d . . . . .
C21 C 0.52399(15) 0.5681(2) 0.26729(11) 0.0146(3) Uani 1 1 d . . . . .
C22 C 0.61670(15) 0.5019(2) 0.23341(11) 0.0164(4) Uani 1 1 d . . . . .
H22 H 0.6028 0.4505 0.1791 0.020 Uiso 1 1 calc R . . . .
C23 C 0.72938(14) 0.5132(2) 0.28114(11) 0.0170(4) Uani 1 1 d . . . . .
H23 H 0.7951 0.4731 0.2597 0.020 Uiso 1 1 calc R . . . .
C24 C 0.74441(17) 0.5843(2) 0.36099(12) 0.0162(4) Uani 1 1 d . . . . .
C25 C 0.64701(16) 0.6420(3) 0.39072(11) 0.0172(4) Uani 1 1 d . . . . .
H25 H 0.6582 0.6876 0.4460 0.021 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C24 1.8845(19) . ?
N1 C1 1.403(2) . ?
N1 C12 1.400(2) . ?
N1 C21 1.411(2) . ?
N2 C21 1.338(2) . ?
N2 C25 1.339(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.386(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.438(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.417(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.396(3) . ?
C21 C22 1.395(3) . ?
C22 C23 1.382(2) . ?
C23 C24 1.387(3) . ?
C24 C25 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C21 125.52(15) . . ?
C12 N1 C1 108.32(15) . . ?
C12 N1 C21 126.15(16) . . ?
C21 N2 C25 117.68(16) . . ?
N1 C1 C6 108.66(16) . . ?
C2 C1 N1 129.68(16) . . ?
C2 C1 C6 121.57(16) . . ?
C3 C2 C1 117.64(18) . . ?
C2 C3 C4 121.41(19) . . ?
C5 C4 C3 120.82(18) . . ?
C4 C5 C6 118.67(18) . . ?
C1 C6 C7 107.57(16) . . ?
C5 C6 C1 119.87(18) . . ?
C5 C6 C7 132.50(17) . . ?
C8 C7 C6 133.34(18) . . ?
C8 C7 C12 119.84(19) . . ?
C12 C7 C6 106.82(17) . . ?
C9 C8 C7 119.40(18) . . ?
C8 C9 C10 120.26(18) . . ?
C11 C10 C9 121.58(18) . . ?
C10 C11 C12 118.09(17) . . ?
N1 C12 C7 108.63(17) . . ?
C11 C12 N1 130.54(17) . . ?
C11 C12 C7 120.81(18) . . ?
N2 C21 N1 115.69(16) . . ?
N2 C21 C22 123.62(17) . . ?
C22 C21 N1 120.68(16) . . ?
C23 C22 C21 118.12(17) . . ?
C22 C23 C24 118.58(16) . . ?
C23 C24 Br1 120.84(14) . . ?
C25 C24 Br1 119.58(15) . . ?
C25 C24 C23 119.57(17) . . ?
N2 C25 C24 122.38(18) . . ?

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 C24 C25 N2 179.46(13) . . . . ?
N1 C1 C2 C3 -175.47(18) . . . . ?
N1 C1 C6 C5 177.01(15) . . . . ?
N1 C1 C6 C7 -0.53(19) . . . . ?
N1 C21 C22 C23 178.99(16) . . . . ?
N2 C21 C22 C23 -2.4(3) . . . . ?
C1 N1 C12 C7 -0.17(18) . . . . ?
C1 N1 C12 C11 178.19(18) . . . . ?
C1 N1 C21 N2 -37.5(2) . . . . ?
C1 N1 C21 C22 141.19(17) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C6 C7 C8 -179.54(18) . . . . ?
C1 C6 C7 C12 0.42(19) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -177.39(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 175.88(19) . . . . ?
C5 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C12 -176.69(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C7 C8 C9 179.43(19) . . . . ?
C6 C7 C12 N1 -0.15(19) . . . . ?
C6 C7 C12 C11 -178.70(15) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C7 C12 N1 179.81(15) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 N1 -178.76(17) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C12 N1 C1 C2 176.97(17) . . . . ?
C12 N1 C1 C6 0.44(19) . . . . ?
C12 N1 C21 N2 141.97(17) . . . . ?
C12 N1 C21 C22 -39.3(3) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
C21 N1 C1 C2 -3.5(3) . . . . ?
C21 N1 C1 C6 180.00(15) . . . . ?
C21 N1 C12 C7 -179.73(15) . . . . ?
C21 N1 C12 C11 -1.4(3) . . . . ?
C21 N2 C25 C24 1.1(3) . . . . ?
C21 C22 C23 C24 1.9(3) . . . . ?
C22 C23 C24 Br1 178.96(12) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 N2 -1.5(3) . . . . ?
C25 N2 C21 N1 179.58(15) . . . . ?
C25 N2 C21 C22 0.9(3) . . . . ?

_olex2_date_sample_data_collection 2017-04-25
_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_wjg11cult
_database_code_depnum_ccdc_archive 'CCDC 2085871'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.3832(2)
_cell_length_b                   11.72436(15)
_cell_length_c                   16.3283(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.6388(18)
_cell_angle_gamma                90
_cell_volume                     2502.81(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      75.3780
_cell_measurement_theta_min      4.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9254
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.474
_diffrn_reflns_theta_min         3.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00 176.00   1.00    3.00    --  110.57  15.00 -30.00  126
  2  ω    -30.00  23.00   1.00    2.00    --   40.57 -57.00 -30.00   53
  3  ω    -62.00  31.00   1.00    2.00    --  -40.57  37.00-150.00   93
  4  ω   -116.00 -14.00   1.00    2.00    --  -40.57 -37.00  30.00  102
  5  ω    103.00 134.00   1.00    3.00    --  110.57 125.00-150.00   31
  6  ω     97.00 178.00   1.00    3.00    --  110.57  45.00-180.00   81
  7  ω     42.00 141.00   1.00    3.00    --  110.57 -61.00 120.00   99
  8  ω     35.00  75.00   1.00    3.00    --  110.57 -94.00 120.00   40
  9  ω     26.00  95.00   1.00    3.00    --  110.57 -94.00 -30.00   69
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0784717000
_diffrn_orient_matrix_UB_12      0.0890996000
_diffrn_orient_matrix_UB_13      -0.0579100000
_diffrn_orient_matrix_UB_21      -0.0666600000
_diffrn_orient_matrix_UB_22      -0.0252631000
_diffrn_orient_matrix_UB_23      0.0511705000
_diffrn_orient_matrix_UB_31      0.0574190000
_diffrn_orient_matrix_UB_32      0.0931283000
_diffrn_orient_matrix_UB_33      0.0693815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4219
_reflns_number_total             4490
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.8100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0784
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C22(H22),
 C23(H23), C24(H24), C25(H25), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A),
  C9A(H9A), C10A(H10A), C11A(H11A), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40493(7) 0.59236(8) 0.84714(6) 0.0203(2) Uani 1 1 d . . . . .
N2 N 0.53673(7) 0.60052(8) 0.80026(6) 0.0225(2) Uani 1 1 d . . . . .
C1 C 0.42229(8) 0.68661(9) 0.90391(7) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.51423(8) 0.73865(9) 0.95931(7) 0.0224(2) Uani 1 1 d . . . . .
H2 H 0.5776 0.7133 0.9608 0.027 Uiso 1 1 calc R . . . .
C3 C 0.50938(9) 0.82885(10) 1.01222(7) 0.0241(2) Uani 1 1 d . . . . .
H3 H 0.5708 0.8663 1.0504 0.029 Uiso 1 1 calc R . . . .
C4 C 0.41620(9) 0.86637(10) 1.01086(7) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.4155 0.9282 1.0482 0.029 Uiso 1 1 calc R . . . .
C5 C 0.32537(9) 0.81430(9) 0.95574(7) 0.0222(2) Uani 1 1 d . . . . .
H5 H 0.2623 0.8395 0.9551 0.027 Uiso 1 1 calc R . . . .
C6 C 0.32794(8) 0.72416(9) 0.90102(7) 0.0197(2) Uani 1 1 d . . . . .
C7 C 0.24968(8) 0.65249(9) 0.83663(7) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.14300(8) 0.65182(9) 0.80230(7) 0.0210(2) Uani 1 1 d . . . . .
H8 H 0.1080 0.7058 0.8226 0.025 Uiso 1 1 calc R . . . .
C9 C 0.08924(8) 0.57133(10) 0.73822(7) 0.0220(2) Uani 1 1 d . . . . .
H9 H 0.0167 0.5703 0.7141 0.026 Uiso 1 1 calc R . . . .
C10 C 0.14043(8) 0.49105(9) 0.70828(7) 0.0218(2) Uani 1 1 d . . . . .
H10 H 0.1017 0.4361 0.6646 0.026 Uiso 1 1 calc R . . . .
C11 C 0.24613(8) 0.48997(9) 0.74099(7) 0.0207(2) Uani 1 1 d . . . . .
H11 H 0.2806 0.4357 0.7204 0.025 Uiso 1 1 calc R . . . .
C12 C 0.29996(8) 0.57175(9) 0.80530(7) 0.0189(2) Uani 1 1 d . . . . .
C21 C 0.48068(8) 0.53465(9) 0.82843(7) 0.0188(2) Uani 1 1 d . . . . .
C22 C 0.49335(9) 0.41792(10) 0.84061(8) 0.0269(3) Uani 1 1 d . . . . .
H22 H 0.4516 0.3746 0.8613 0.032 Uiso 1 1 calc R . . . .
C23 C 0.56887(9) 0.36614(10) 0.82166(8) 0.0299(3) Uani 1 1 d . . . . .
H23 H 0.5799 0.2862 0.8291 0.036 Uiso 1 1 calc R . . . .
C24 C 0.62782(8) 0.43275(10) 0.79186(8) 0.0262(2) Uani 1 1 d . . . . .
H24 H 0.6798 0.3996 0.7780 0.031 Uiso 1 1 calc R . . . .
C25 C 0.60933(8) 0.54849(10) 0.78275(8) 0.0260(2) Uani 1 1 d . . . . .
H25 H 0.6506 0.5940 0.7629 0.031 Uiso 1 1 calc R . . . .
N1A N 0.27388(7) 0.57296(8) 0.43503(6) 0.02005(19) Uani 1 1 d . . . . .
N2A N 0.28429(7) 0.77133(8) 0.44246(6) 0.0222(2) Uani 1 1 d . . . . .
C1A C 0.20350(8) 0.55525(9) 0.34587(7) 0.0192(2) Uani 1 1 d . . . . .
C2A C 0.12752(8) 0.62786(9) 0.28867(7) 0.0217(2) Uani 1 1 d . . . . .
H2A H 0.1163 0.7009 0.3080 0.026 Uiso 1 1 calc R . . . .
C3A C 0.06897(8) 0.58866(10) 0.20219(7) 0.0238(2) Uani 1 1 d . . . . .
H3A H 0.0167 0.6362 0.1614 0.029 Uiso 1 1 calc R . . . .
C4A C 0.08475(8) 0.48115(10) 0.17332(7) 0.0249(2) Uani 1 1 d . . . . .
H4A H 0.0445 0.4580 0.1130 0.030 Uiso 1 1 calc R . . . .
C5A C 0.15807(8) 0.40803(10) 0.23118(7) 0.0233(2) Uani 1 1 d . . . . .
H5A H 0.1675 0.3342 0.2118 0.028 Uiso 1 1 calc R . . . .
C6A C 0.21835(8) 0.44512(9) 0.31921(7) 0.0199(2) Uani 1 1 d . . . . .
C7A C 0.30166(8) 0.39433(9) 0.39517(7) 0.0207(2) Uani 1 1 d . . . . .
C8A C 0.35193(9) 0.28973(10) 0.40806(8) 0.0264(2) Uani 1 1 d . . . . .
H8A H 0.3298 0.2337 0.3618 0.032 Uiso 1 1 calc R . . . .
C9A C 0.43428(9) 0.26885(10) 0.48899(8) 0.0305(3) Uani 1 1 d . . . . .
H9A H 0.4690 0.1978 0.4984 0.037 Uiso 1 1 calc R . . . .
C10A C 0.46716(9) 0.35098(10) 0.55720(8) 0.0281(3) Uani 1 1 d . . . . .
H10A H 0.5245 0.3349 0.6121 0.034 Uiso 1 1 calc R . . . .
C11A C 0.41825(8) 0.45519(10) 0.54671(7) 0.0239(2) Uani 1 1 d . . . . .
H11A H 0.4408 0.5107 0.5933 0.029 Uiso 1 1 calc R . . . .
C12A C 0.33462(8) 0.47549(9) 0.46500(7) 0.0198(2) Uani 1 1 d . . . . .
C21A C 0.28371(8) 0.67447(9) 0.48486(7) 0.0198(2) Uani 1 1 d . . . . .
C22A C 0.29077(8) 0.66885(10) 0.57250(7) 0.0240(2) Uani 1 1 d . . . . .
H22A H 0.2895 0.5976 0.5997 0.029 Uiso 1 1 calc R . . . .
C23A C 0.29959(9) 0.76973(10) 0.61861(8) 0.0275(3) Uani 1 1 d . . . . .
H23A H 0.3057 0.7692 0.6788 0.033 Uiso 1 1 calc R . . . .
C24A C 0.29939(8) 0.87196(10) 0.57582(8) 0.0267(3) Uani 1 1 d . . . . .
H24A H 0.3047 0.9428 0.6057 0.032 Uiso 1 1 calc R . . . .
C25A C 0.29128(8) 0.86807(10) 0.48830(8) 0.0246(2) Uani 1 1 d . . . . .
H25A H 0.2906 0.9383 0.4590 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3964(14) . ?
N1 C12 1.3945(13) . ?
N1 C21 1.4198(13) . ?
N2 C21 1.3293(14) . ?
N2 C25 1.3391(14) . ?
C1 C2 1.3934(15) . ?
C1 C6 1.4086(15) . ?
C2 C3 1.3855(16) . ?
C3 C4 1.4019(16) . ?
C4 C5 1.3818(16) . ?
C5 C6 1.3944(15) . ?
C6 C7 1.4462(15) . ?
C7 C8 1.3970(15) . ?
C7 C12 1.4104(15) . ?
C8 C9 1.3815(16) . ?
C9 C10 1.4025(16) . ?
C10 C11 1.3855(15) . ?
C11 C12 1.3941(15) . ?
C21 C22 1.3840(16) . ?
C22 C23 1.3871(17) . ?
C23 C24 1.3819(17) . ?
C24 C25 1.3788(17) . ?
N1A C1A 1.3995(13) . ?
N1A C12A 1.3972(14) . ?
N1A C21A 1.4151(14) . ?
N2A C21A 1.3318(14) . ?
N2A C25A 1.3394(15) . ?
C1A C2A 1.3929(15) . ?
C1A C6A 1.4070(15) . ?
C2A C3A 1.3867(15) . ?
C3A C4A 1.3971(17) . ?
C4A C5A 1.3816(17) . ?
C5A C6A 1.4028(15) . ?
C6A C7A 1.4456(15) . ?
C7A C8A 1.3944(16) . ?
C7A C12A 1.4070(15) . ?
C8A C9A 1.3799(17) . ?
C9A C10A 1.3972(18) . ?
C10A C11A 1.3844(16) . ?
C11A C12A 1.3947(15) . ?
C21A C22A 1.3932(15) . ?
C22A C23A 1.3792(16) . ?
C23A C24A 1.3869(17) . ?
C24A C25A 1.3852(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C21 125.39(9) . . ?
C12 N1 C1 108.65(9) . . ?
C12 N1 C21 125.68(9) . . ?
C21 N2 C25 116.66(10) . . ?
N1 C1 C6 108.78(9) . . ?
C2 C1 N1 129.51(10) . . ?
C2 C1 C6 121.68(10) . . ?
C3 C2 C1 117.27(10) . . ?
C2 C3 C4 121.73(10) . . ?
C5 C4 C3 120.64(10) . . ?
C4 C5 C6 118.80(10) . . ?
C1 C6 C7 106.85(9) . . ?
C5 C6 C1 119.86(10) . . ?
C5 C6 C7 133.28(10) . . ?
C8 C7 C6 133.38(10) . . ?
C8 C7 C12 119.62(10) . . ?
C12 C7 C6 106.99(9) . . ?
C9 C8 C7 118.82(10) . . ?
C8 C9 C10 120.86(10) . . ?
C11 C10 C9 121.53(10) . . ?
C10 C11 C12 117.36(10) . . ?
N1 C12 C7 108.68(9) . . ?
C11 C12 N1 129.50(10) . . ?
C11 C12 C7 121.81(10) . . ?
N2 C21 N1 115.34(9) . . ?
N2 C21 C22 124.18(10) . . ?
C22 C21 N1 120.48(10) . . ?
C21 C22 C23 117.98(11) . . ?
C24 C23 C22 118.92(11) . . ?
C25 C24 C23 118.37(10) . . ?
N2 C25 C24 123.90(11) . . ?
C1A N1A C21A 125.34(9) . . ?
C12A N1A C1A 108.57(9) . . ?
C12A N1A C21A 126.05(9) . . ?
C21A N2A C25A 116.54(9) . . ?
N1A C1A C6A 108.71(9) . . ?
C2A C1A N1A 129.19(10) . . ?
C2A C1A C6A 122.09(10) . . ?
C3A C2A C1A 116.99(10) . . ?
C2A C3A C4A 121.84(10) . . ?
C5A C4A C3A 120.94(10) . . ?
C4A C5A C6A 118.54(10) . . ?
C1A C6A C7A 106.92(9) . . ?
C5A C6A C1A 119.53(10) . . ?
C5A C6A C7A 133.52(10) . . ?
C8A C7A C6A 133.16(10) . . ?
C8A C7A C12A 119.62(10) . . ?
C12A C7A C6A 107.18(9) . . ?
C9A C8A C7A 118.99(11) . . ?
C8A C9A C10A 120.75(11) . . ?
C11A C10A C9A 121.60(11) . . ?
C10A C11A C12A 117.40(11) . . ?
N1A C12A C7A 108.60(9) . . ?
C11A C12A N1A 129.69(10) . . ?
C11A C12A C7A 121.64(10) . . ?
N2A C21A N1A 116.04(9) . . ?
N2A C21A C22A 124.10(10) . . ?
C22A C21A N1A 119.86(10) . . ?
C23A C22A C21A 118.09(10) . . ?
C22A C23A C24A 119.06(10) . . ?
C25A C24A C23A 118.22(11) . . ?
N2A C25A C24A 123.97(11) . . ?

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
N1 C1 C2 C3 -177.09(10) . . . . ?
N1 C1 C6 C5 176.80(9) . . . . ?
N1 C1 C6 C7 -2.56(11) . . . . ?
N1 C21 C22 C23 -179.70(10) . . . . ?
N2 C21 C22 C23 -0.44(17) . . . . ?
C1 N1 C12 C7 -0.91(11) . . . . ?
C1 N1 C12 C11 177.40(10) . . . . ?
C1 N1 C21 N2 -52.92(14) . . . . ?
C1 N1 C21 C22 126.41(12) . . . . ?
C1 C2 C3 C4 0.35(16) . . . . ?
C1 C6 C7 C8 -176.44(11) . . . . ?
C1 C6 C7 C12 1.98(11) . . . . ?
C2 C1 C6 C5 -1.15(16) . . . . ?
C2 C1 C6 C7 179.49(10) . . . . ?
C2 C3 C4 C5 -0.36(17) . . . . ?
C3 C4 C5 C6 -0.40(16) . . . . ?
C4 C5 C6 C1 1.12(15) . . . . ?
C4 C5 C6 C7 -179.71(11) . . . . ?
C5 C6 C7 C8 4.3(2) . . . . ?
C5 C6 C7 C12 -177.26(11) . . . . ?
C6 C1 C2 C3 0.40(16) . . . . ?
C6 C7 C8 C9 178.39(11) . . . . ?
C6 C7 C12 N1 -0.68(11) . . . . ?
C6 C7 C12 C11 -179.14(9) . . . . ?
C7 C8 C9 C10 0.37(15) . . . . ?
C8 C7 C12 N1 178.00(9) . . . . ?
C8 C7 C12 C11 -0.46(15) . . . . ?
C8 C9 C10 C11 -0.56(16) . . . . ?
C9 C10 C11 C12 0.23(15) . . . . ?
C10 C11 C12 N1 -177.83(10) . . . . ?
C10 C11 C12 C7 0.27(15) . . . . ?
C12 N1 C1 C2 179.92(11) . . . . ?
C12 N1 C1 C6 2.19(12) . . . . ?
C12 N1 C21 N2 120.30(11) . . . . ?
C12 N1 C21 C22 -60.37(15) . . . . ?
C12 C7 C8 C9 0.12(15) . . . . ?
C21 N1 C1 C2 -5.88(17) . . . . ?
C21 N1 C1 C6 176.38(9) . . . . ?
C21 N1 C12 C7 -175.08(9) . . . . ?
C21 N1 C12 C11 3.23(18) . . . . ?
C21 N2 C25 C24 0.37(16) . . . . ?
C21 C22 C23 C24 0.11(17) . . . . ?
C22 C23 C24 C25 0.40(17) . . . . ?
C23 C24 C25 N2 -0.67(18) . . . . ?
C25 N2 C21 N1 179.50(9) . . . . ?
C25 N2 C21 C22 0.21(16) . . . . ?
N1A C1A C2A C3A 179.07(10) . . . . ?
N1A C1A C6A C5A -178.53(9) . . . . ?
N1A C1A C6A C7A -0.43(11) . . . . ?
N1A C21A C22A C23A -179.58(10) . . . . ?
N2A C21A C22A C23A -0.44(16) . . . . ?
C1A N1A C12A C7A -1.06(11) . . . . ?
C1A N1A C12A C11A 175.98(10) . . . . ?
C1A N1A C21A N2A -45.94(14) . . . . ?
C1A N1A C21A C22A 133.27(11) . . . . ?
C1A C2A C3A C4A 0.24(16) . . . . ?
C1A C6A C7A C8A -177.84(11) . . . . ?
C1A C6A C7A C12A -0.22(11) . . . . ?
C2A C1A C6A C5A 2.76(15) . . . . ?
C2A C1A C6A C7A -179.14(9) . . . . ?
C2A C3A C4A C5A 1.81(16) . . . . ?
C3A C4A C5A C6A -1.56(16) . . . . ?
C4A C5A C6A C1A -0.65(15) . . . . ?
C4A C5A C6A C7A -178.14(11) . . . . ?
C5A C6A C7A C8A -0.1(2) . . . . ?
C5A C6A C7A C12A 177.51(11) . . . . ?
C6A C1A C2A C3A -2.51(15) . . . . ?
C6A C7A C8A C9A 176.41(11) . . . . ?
C6A C7A C12A N1A 0.78(11) . . . . ?
C6A C7A C12A C11A -176.54(10) . . . . ?
C7A C8A C9A C10A -0.04(18) . . . . ?
C8A C7A C12A N1A 178.78(9) . . . . ?
C8A C7A C12A C11A 1.46(16) . . . . ?
C8A C9A C10A C11A 0.63(18) . . . . ?
C9A C10A C11A C12A -0.17(17) . . . . ?
C10A C11A C12A N1A -177.58(10) . . . . ?
C10A C11A C12A C7A -0.87(16) . . . . ?
C12A N1A C1A C2A 179.51(10) . . . . ?
C12A N1A C1A C6A 0.92(11) . . . . ?
C12A N1A C21A N2A 131.63(11) . . . . ?
C12A N1A C21A C22A -49.16(15) . . . . ?
C12A C7A C8A C9A -0.97(16) . . . . ?
C21A N1A C1A C2A -2.56(17) . . . . ?
C21A N1A C1A C6A 178.85(9) . . . . ?
C21A N1A C12A C7A -178.97(9) . . . . ?
C21A N1A C12A C11A -1.93(18) . . . . ?
C21A N2A C25A C24A 1.06(16) . . . . ?
C21A C22A C23A C24A 1.04(16) . . . . ?
C22A C23A C24A C25A -0.62(17) . . . . ?
C23A C24A C25A N2A -0.47(17) . . . . ?
C25A N2A C21A N1A 178.58(9) . . . . ?
C25A N2A C21A C22A -0.60(15) . . . . ?

_olex2_date_sample_data_collection 2017-07-10
_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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_wjg12cult
_database_code_depnum_ccdc_archive 'CCDC 2085872'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H11 N3'
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 N2 H15'
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      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                   25.4249(16)
_cell_length_b                   5.1479(3)
_cell_length_c                   19.2278(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.349(8)
_cell_angle_gamma                90
_cell_volume                     2343.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    99.94(15)
_cell_measurement_theta_max      75.5070
_cell_measurement_theta_min      3.7140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3510
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.494
_diffrn_reflns_theta_min         3.733
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.94(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_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     52.00 111.00   1.00    1.00    --  110.57 -45.00 -30.00   59
  2  ω    -85.00  -2.00   1.00    1.00    --  -40.57 125.00 -30.00   83
  3  ω   -105.00  -9.00   1.00    1.00    --  -40.57 -77.00-150.00   96
  4  ω     59.00 114.00   1.00    1.00    --  110.57-111.00 -60.00   55
  5  ω     26.00 102.00   1.00    1.00    --  110.57 -94.00-180.00   76
  6  ω     96.00 178.00   1.00    1.00    --  110.57  30.00 -60.00   82
  7  ω    116.00 172.00   1.00    1.00    --  110.57 111.00-120.00   56
  8  ω    101.00 178.00   1.00    1.00    --  110.57 111.00 120.00   77
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0364621000
_diffrn_orient_matrix_UB_12      0.0506932000
_diffrn_orient_matrix_UB_13      -0.0825164000
_diffrn_orient_matrix_UB_21      0.0035267000
_diffrn_orient_matrix_UB_22      0.2946920000
_diffrn_orient_matrix_UB_23      0.0151251000
_diffrn_orient_matrix_UB_31      0.0537112000
_diffrn_orient_matrix_UB_32      0.0144330000
_diffrn_orient_matrix_UB_33      -0.0191452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1826
_reflns_number_total             2081
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.024
_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)+(0.0500P)²+0.7278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C21(H21),
 C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13212(4) 0.49483(19) 0.30582(5) 0.0191(2) Uani 1 1 d . . . . .
N2 N 0.07639(4) 0.8422(2) 0.31479(6) 0.0233(2) Uani 1 1 d . . . . .
N3 N 0.15283(4) 0.6918(2) 0.42172(6) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.09941(5) 0.4361(2) 0.23027(7) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.05063(5) 0.5534(2) 0.18019(7) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.0333 0.6961 0.1948 0.029 Uiso 1 1 calc R . . . .
C3 C 0.02851(5) 0.4532(3) 0.10830(7) 0.0268(3) Uani 1 1 d . . . . .
H3 H -0.0043 0.5313 0.0732 0.032 Uiso 1 1 calc R . . . .
C4 C 0.05268(5) 0.2423(3) 0.08573(7) 0.0274(3) Uani 1 1 d . . . . .
H4 H 0.0362 0.1788 0.0361 0.033 Uiso 1 1 calc R . . . .
C5 C 0.10064(5) 0.1247(3) 0.13553(7) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.1172 -0.0204 0.1207 0.030 Uiso 1 1 calc R . . . .
C6 C 0.12412(5) 0.2239(2) 0.20787(7) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.17383(5) 0.1503(2) 0.27050(7) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.21394(5) -0.0436(2) 0.27852(7) 0.0226(3) Uani 1 1 d . . . . .
H8 H 0.2103 -0.1605 0.2388 0.027 Uiso 1 1 calc R . . . .
C9 C 0.25913(5) -0.0622(2) 0.34544(7) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.2867 -0.1941 0.3521 0.029 Uiso 1 1 calc R . . . .
C10 C 0.26451(5) 0.1116(3) 0.40334(7) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.2963 0.0975 0.4486 0.029 Uiso 1 1 calc R . . . .
C11 C 0.22477(5) 0.3047(2) 0.39686(7) 0.0220(3) Uani 1 1 d . . . . .
H11 H 0.2288 0.4216 0.4367 0.026 Uiso 1 1 calc R . . . .
C12 C 0.17868(5) 0.3205(2) 0.32955(6) 0.0195(3) Uani 1 1 d . . . . .
C20 C 0.11998(5) 0.6856(2) 0.34940(7) 0.0193(3) Uani 1 1 d . . . . .
C21 C 0.06565(5) 1.0239(3) 0.35726(7) 0.0254(3) Uani 1 1 d . . . . .
H21 H 0.0347 1.1382 0.3349 0.030 Uiso 1 1 calc R . . . .
C22 C 0.09730(5) 1.0536(3) 0.43203(7) 0.0267(3) Uani 1 1 d . . . . .
H22 H 0.0895 1.1860 0.4614 0.032 Uiso 1 1 calc R . . . .
C23 C 0.14100(5) 0.8791(3) 0.46178(7) 0.0279(3) Uani 1 1 d . . . . .
H23 H 0.1637 0.8930 0.5133 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4191(15) . ?
N1 C12 1.4219(14) . ?
N1 C20 1.3965(15) . ?
N2 C20 1.3356(15) . ?
N2 C21 1.3338(16) . ?
N3 C20 1.3366(16) . ?
N3 C23 1.3349(17) . ?
C1 C2 1.4003(17) . ?
C1 C6 1.4035(17) . ?
C2 C3 1.3882(18) . ?
C3 C4 1.393(2) . ?
C4 C5 1.3857(18) . ?
C5 C6 1.3955(17) . ?
C6 C7 1.4434(17) . ?
C7 C8 1.3951(17) . ?
C7 C12 1.4033(17) . ?
C8 C9 1.3814(18) . ?
C9 C10 1.3957(18) . ?
C10 C11 1.3905(17) . ?
C11 C12 1.3966(17) . ?
C21 C22 1.3766(19) . ?
C22 C23 1.3803(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 107.65(10) . . ?
C20 N1 C1 126.08(10) . . ?
C20 N1 C12 126.26(10) . . ?
C21 N2 C20 115.85(11) . . ?
C23 N3 C20 115.52(11) . . ?
C2 C1 N1 130.87(12) . . ?
C2 C1 C6 120.52(12) . . ?
C6 C1 N1 108.60(10) . . ?
C3 C2 C1 117.44(12) . . ?
C2 C3 C4 122.36(12) . . ?
C5 C4 C3 120.16(12) . . ?
C4 C5 C6 118.58(12) . . ?
C1 C6 C7 107.58(10) . . ?
C5 C6 C1 120.93(11) . . ?
C5 C6 C7 131.49(12) . . ?
C8 C7 C6 131.53(11) . . ?
C8 C7 C12 120.79(11) . . ?
C12 C7 C6 107.67(10) . . ?
C9 C8 C7 118.63(11) . . ?
C8 C9 C10 120.35(11) . . ?
C11 C10 C9 122.00(12) . . ?
C10 C11 C12 117.50(11) . . ?
C7 C12 N1 108.46(10) . . ?
C11 C12 N1 130.81(11) . . ?
C11 C12 C7 120.70(11) . . ?
N2 C20 N1 116.75(11) . . ?
N2 C20 N3 126.49(11) . . ?
N3 C20 N1 116.75(10) . . ?
N2 C21 C22 123.02(11) . . ?
C21 C22 C23 115.91(12) . . ?
N3 C23 C22 123.18(12) . . ?

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
N1 C1 C2 C3 178.86(11) . . . . ?
N1 C1 C6 C5 -179.78(10) . . . . ?
N1 C1 C6 C7 -0.75(12) . . . . ?
N2 C21 C22 C23 -1.13(19) . . . . ?
C1 N1 C12 C7 -2.02(12) . . . . ?
C1 N1 C12 C11 176.02(12) . . . . ?
C1 N1 C20 N2 -6.39(17) . . . . ?
C1 N1 C20 N3 173.02(10) . . . . ?
C1 C2 C3 C4 0.79(18) . . . . ?
C1 C6 C7 C8 -179.15(12) . . . . ?
C1 C6 C7 C12 -0.50(13) . . . . ?
C2 C1 C6 C5 -0.24(17) . . . . ?
C2 C1 C6 C7 178.79(10) . . . . ?
C2 C3 C4 C5 -0.19(19) . . . . ?
C3 C4 C5 C6 -0.63(18) . . . . ?
C4 C5 C6 C1 0.84(17) . . . . ?
C4 C5 C6 C7 -177.93(12) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C12 178.39(12) . . . . ?
C6 C1 C2 C3 -0.57(17) . . . . ?
C6 C7 C8 C9 177.42(12) . . . . ?
C6 C7 C12 N1 1.56(12) . . . . ?
C6 C7 C12 C11 -176.72(10) . . . . ?
C7 C8 C9 C10 -0.54(18) . . . . ?
C8 C7 C12 N1 -179.62(10) . . . . ?
C8 C7 C12 C11 2.11(17) . . . . ?
C8 C9 C10 C11 1.20(19) . . . . ?
C9 C10 C11 C12 -0.20(18) . . . . ?
C10 C11 C12 N1 -179.27(11) . . . . ?
C10 C11 C12 C7 -1.43(17) . . . . ?
C12 N1 C1 C2 -177.77(12) . . . . ?
C12 N1 C1 C6 1.71(12) . . . . ?
C12 N1 C20 N2 175.20(10) . . . . ?
C12 N1 C20 N3 -5.39(16) . . . . ?
C12 C7 C8 C9 -1.08(17) . . . . ?
C20 N1 C1 C2 3.6(2) . . . . ?
C20 N1 C1 C6 -176.95(10) . . . . ?
C20 N1 C12 C7 176.63(10) . . . . ?
C20 N1 C12 C11 -5.33(19) . . . . ?
C20 N2 C21 C22 0.61(18) . . . . ?
C20 N3 C23 C22 1.23(19) . . . . ?
C21 N2 C20 N1 -179.65(10) . . . . ?
C21 N2 C20 N3 1.01(18) . . . . ?
C21 C22 C23 N3 0.16(19) . . . . ?
C23 N3 C20 N1 178.77(10) . . . . ?
C23 N3 C20 N2 -1.89(18) . . . . ?

_olex2_date_sample_data_collection 2017-07-18
_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 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.501
####################################################################### 
# 
# 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_dd18025
_database_code_depnum_ccdc_archive 'CCDC 2085875'
loop_
_audit_author_name
_audit_author_address
'Jianguo Wang'
;Inner Mongolia University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'_publ_contact_author_address      Inner Mongolia University_publ_contact_author_email        wangjg@imu.edu.cn_publ_contact_author_id_orcid     0000-0003-0984-9716_publ_contact_author_name         Jianguo Wang_publ_contact_author_phone        0086 15297765892_publ_section_references'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 Br N3'
_chemical_formula_sum            'C16 H10 Br N3'
_chemical_formula_weight         324.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.8257(12)
_cell_length_b                   13.1338(8)
_cell_length_c                   5.5743(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1305.05(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2794
_cell_measurement_theta_min      5.524
_cell_measurement_theta_max      52.202

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.141
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4943
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6993
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.762
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             2444
_reflns_number_gt                1928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.903
_reflns_Friedel_fraction_full    0.904

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.3608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.388(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2444
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.33525(3) 0.97009(4) 1.15745(18) 0.0700(2) Uani 1 1 d . . . . .
N1 N 0.3579(3) 0.7644(3) 0.6057(8) 0.0557(12) Uani 1 1 d . . . . .
N2 N 0.4695(2) 0.8638(3) 0.6127(9) 0.0602(13) Uani 1 1 d . . . . .
N3 N 0.4543(3) 0.7341(3) 0.3338(8) 0.0568(11) Uani 1 1 d . . . . .
C1 C 0.4259(3) 0.7901(4) 0.5269(9) 0.0517(13) Uani 1 1 d . . . . .
C2 C 0.3324(3) 0.8172(4) 0.7915(10) 0.0567(14) Uani 1 1 d . . . . .
H2 H 0.2854 0.8014 0.8537 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3730(3) 0.8944(4) 0.8954(9) 0.0529(13) Uani 1 1 d . . . . .
C4 C 0.4423(4) 0.9155(4) 0.7992(11) 0.0609(15) Uani 1 1 d . . . . .
H4 H 0.4710 0.9673 0.8663 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4156(3) 0.6587(4) 0.2000(10) 0.0579(14) Uani 1 1 d . . . . .
C6 C 0.3456(4) 0.6150(5) 0.2337(11) 0.0687(17) Uani 1 1 d . . . . .
H6 H 0.3147 0.6349 0.3598 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3232(4) 0.5406(5) 0.0731(12) 0.074(2) Uani 1 1 d . . . . .
H7 H 0.2767 0.5099 0.0938 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3678(5) 0.5103(6) -0.1176(14) 0.081(2) Uani 1 1 d . . . . .
H8 H 0.3510 0.4599 -0.2218 0.097 Uiso 1 1 calc R U . . .
C9 C 0.4366(5) 0.5545(5) -0.1530(12) 0.0746(19) Uani 1 1 d . . . . .
H9 H 0.4665 0.5350 -0.2818 0.090 Uiso 1 1 calc R U . . .
C10 C 0.4609(4) 0.6289(4) 0.0072(10) 0.0627(16) Uani 1 1 d . . . . .
C11 C 0.5296(4) 0.6856(5) 0.0213(11) 0.0658(16) Uani 1 1 d . . . . .
C12 C 0.5258(3) 0.7501(4) 0.2222(10) 0.0607(15) Uani 1 1 d . . . . .
C13 C 0.5860(4) 0.8111(5) 0.2832(13) 0.0722(18) Uani 1 1 d . . . . .
H13 H 0.5843 0.8525 0.4185 0.087 Uiso 1 1 calc R U . . .
C14 C 0.6488(4) 0.8091(5) 0.138(2) 0.087(2) Uani 1 1 d . . . . .
H14 H 0.6894 0.8505 0.1754 0.104 Uiso 1 1 calc R U . . .
C15 C 0.6524(5) 0.7469(7) -0.0605(17) 0.094(2) Uani 1 1 d . . . . .
H15 H 0.6954 0.7471 -0.1550 0.112 Uiso 1 1 calc R U . . .
C16 C 0.5935(4) 0.6846(6) -0.1211(13) 0.081(2) Uani 1 1 d . . . . .
H16 H 0.5964 0.6425 -0.2549 0.097 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 C3 1.891(5) . ?
N1 C2 1.327(7) . ?
N1 C1 1.333(7) . ?
N2 C1 1.330(7) . ?
N2 C4 1.333(7) . ?
N3 C1 1.399(7) . ?
N3 C5 1.420(7) . ?
N3 C12 1.433(8) . ?
C2 C3 1.373(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(8) . ?
C5 C10 1.400(7) . ?
C6 C7 1.384(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.434(9) . ?
C11 C16 1.389(9) . ?
C11 C12 1.406(8) . ?
C12 C13 1.382(8) . ?
C13 C14 1.381(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(11) . ?
C15 H15 0.9300 . ?
C16 H16 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
C2 N1 C1 115.8(5) . . ?
C1 N2 C4 116.1(5) . . ?
C1 N3 C5 126.5(5) . . ?
C1 N3 C12 125.4(5) . . ?
C5 N3 C12 107.9(5) . . ?
N2 C1 N1 126.7(5) . . ?
N2 C1 N3 116.6(5) . . ?
N1 C1 N3 116.7(5) . . ?
N1 C2 C3 122.3(5) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 117.3(5) . . ?
C2 C3 Br1 121.8(4) . . ?
C4 C3 Br1 120.9(4) . . ?
N2 C4 C3 121.8(5) . . ?
N2 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C10 120.5(5) . . ?
C6 C5 N3 131.0(5) . . ?
C10 C5 N3 108.5(5) . . ?
C7 C6 C5 117.6(6) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C8 122.3(7) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 120.1(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 118.9(7) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C5 120.5(6) . . ?
C9 C10 C11 131.6(6) . . ?
C5 C10 C11 107.8(5) . . ?
C16 C11 C12 120.0(7) . . ?
C16 C11 C10 131.6(6) . . ?
C12 C11 C10 108.4(5) . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 N3 131.9(6) . . ?
C11 C12 N3 107.5(6) . . ?
C14 C13 C12 118.3(7) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C13 121.4(7) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 121.0(7) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 118.8(7) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 C1 N1 1.3(8) . . . . ?
C4 N2 C1 N3 -178.9(4) . . . . ?
C2 N1 C1 N2 -1.3(7) . . . . ?
C2 N1 C1 N3 178.9(4) . . . . ?
C5 N3 C1 N2 -173.9(5) . . . . ?
C12 N3 C1 N2 -0.2(7) . . . . ?
C5 N3 C1 N1 5.9(7) . . . . ?
C12 N3 C1 N1 179.6(5) . . . . ?
C1 N1 C2 C3 0.7(7) . . . . ?
N1 C2 C3 C4 -0.2(8) . . . . ?
N1 C2 C3 Br1 179.1(4) . . . . ?
C1 N2 C4 C3 -0.6(8) . . . . ?
C2 C3 C4 N2 0.1(8) . . . . ?
Br1 C3 C4 N2 -179.2(4) . . . . ?
C1 N3 C5 C6 -6.5(8) . . . . ?
C12 N3 C5 C6 178.9(5) . . . . ?
C1 N3 C5 C10 173.8(4) . . . . ?
C12 N3 C5 C10 -0.8(5) . . . . ?
C10 C5 C6 C7 0.9(7) . . . . ?
N3 C5 C6 C7 -178.7(5) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C9 -0.2(10) . . . . ?
C7 C8 C9 C10 0.8(9) . . . . ?
C8 C9 C10 C5 -0.5(8) . . . . ?
C8 C9 C10 C11 177.9(6) . . . . ?
C6 C5 C10 C9 -0.3(7) . . . . ?
N3 C5 C10 C9 179.4(5) . . . . ?
C6 C5 C10 C11 -179.1(5) . . . . ?
N3 C5 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C16 0.3(10) . . . . ?
C5 C10 C11 C16 178.9(6) . . . . ?
C9 C10 C11 C12 -178.8(6) . . . . ?
C5 C10 C11 C12 -0.2(6) . . . . ?
C16 C11 C12 C13 -1.5(8) . . . . ?
C10 C11 C12 C13 177.7(5) . . . . ?
C16 C11 C12 N3 -179.5(5) . . . . ?
C10 C11 C12 N3 -0.3(6) . . . . ?
C1 N3 C12 C13 8.3(9) . . . . ?
C5 N3 C12 C13 -177.0(6) . . . . ?
C1 N3 C12 C11 -174.0(4) . . . . ?
C5 N3 C12 C11 0.7(5) . . . . ?
C11 C12 C13 C14 1.8(9) . . . . ?
N3 C12 C13 C14 179.3(6) . . . . ?
C12 C13 C14 C15 -1.1(11) . . . . ?
C13 C14 C15 C16 0.0(12) . . . . ?
C14 C15 C16 C11 0.3(11) . . . . ?
C12 C11 C16 C15 0.4(9) . . . . ?
C10 C11 C16 C15 -178.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 N2 0.93 2.32 2.858(8) 116.4 .
C13 H13 Br1 0.93 3.04 3.819(7) 141.9 2_674
C6 H6 N1 0.93 2.32 2.864(8) 117.2 .
C6 H6 N1 0.93 2.32 2.864(8) 117.2 .
C13 H13 Br1 0.93 3.04 3.819(7) 141.9 2_674
C13 H13 N2 0.93 2.32 2.858(8) 116.4 .

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



