# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1917793'
loop_
_audit_author_name
_audit_author_address
'Yanhui Wang'
;Qingdao university of science and technology
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        9-phenyl-9H-carbazole-2-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   11.1664(15)
_cell_length_b                   11.040(4)
_cell_length_c                   11.208(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.792(6)
_cell_angle_gamma                90.00
_cell_volume                     1365.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1081
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6715
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2400
_reflns_number_gt                1583
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0166(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2400
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21968(12) 1.01360(12) 0.13542(13) 0.0451(4) Uani 1 1 d . . .
N2 N -0.17547(17) 0.98076(19) 0.43676(19) 0.0878(6) Uani 1 1 d . . .
C1 C 0.24595(14) 0.95628(15) 0.03235(16) 0.0422(4) Uani 1 1 d . . .
C2 C 0.34010(15) 0.97580(16) -0.03160(16) 0.0484(5) Uani 1 1 d . . .
H2A H 0.3983 1.0347 -0.0074 0.058 Uiso 1 1 calc R . .
C3 C 0.34589(16) 0.90615(17) -0.13187(17) 0.0541(5) Uani 1 1 d . . .
H3A H 0.4085 0.9186 -0.1764 0.065 Uiso 1 1 calc R . .
C4 C 0.25986(17) 0.81732(17) -0.16809(19) 0.0599(6) Uani 1 1 d . . .
H4A H 0.2663 0.7704 -0.2357 0.072 Uiso 1 1 calc R . .
C5 C 0.16643(17) 0.79848(16) -0.10561(18) 0.0565(5) Uani 1 1 d . . .
H5A H 0.1089 0.7392 -0.1306 0.068 Uiso 1 1 calc R . .
C6 C 0.15711(14) 0.86830(15) -0.00395(16) 0.0443(5) Uani 1 1 d . . .
C7 C 0.07206(14) 0.87423(14) 0.07998(16) 0.0438(4) Uani 1 1 d . . .
C8 C -0.03584(16) 0.81523(16) 0.08917(18) 0.0534(5) Uani 1 1 d . . .
H8A H -0.0649 0.7556 0.0336 0.064 Uiso 1 1 calc R . .
C9 C -0.09907(16) 0.84476(17) 0.17948(19) 0.0561(5) Uani 1 1 d . . .
H9A H -0.1715 0.8052 0.1853 0.067 Uiso 1 1 calc R . .
C10 C -0.05604(15) 0.93426(16) 0.26389(17) 0.0498(5) Uani 1 1 d . . .
C11 C 0.05158(15) 0.99433(16) 0.25750(17) 0.0493(5) Uani 1 1 d . . .
H11A H 0.0808 1.0531 0.3140 0.059 Uiso 1 1 calc R . .
C12 C 0.11391(14) 0.96431(15) 0.16512(16) 0.0433(4) Uani 1 1 d . . .
C13 C -0.12241(17) 0.96188(19) 0.3594(2) 0.0608(6) Uani 1 1 d . . .
C14 C 0.30031(14) 1.09312(15) 0.20846(17) 0.0465(5) Uani 1 1 d . . .
C15 C 0.33373(16) 1.20076(16) 0.16133(19) 0.0564(5) Uani 1 1 d . . .
H15A H 0.3011 1.2233 0.0831 0.068 Uiso 1 1 calc R . .
C16 C 0.41576(18) 1.27497(19) 0.2306(2) 0.0716(7) Uani 1 1 d . . .
H16A H 0.4388 1.3478 0.1991 0.086 Uiso 1 1 calc R . .
C17 C 0.4632(2) 1.2420(2) 0.3450(3) 0.0825(8) Uani 1 1 d . . .
H17A H 0.5198 1.2917 0.3908 0.099 Uiso 1 1 calc R . .
C18 C 0.4285(2) 1.1365(2) 0.3933(2) 0.0831(7) Uani 1 1 d . . .
H18A H 0.4601 1.1155 0.4722 0.100 Uiso 1 1 calc R . .
C19 C 0.34614(17) 1.06058(19) 0.32476(18) 0.0647(6) Uani 1 1 d . . .
H19A H 0.3222 0.9885 0.3571 0.078 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 C12 1.386(2) . ?
N1 C1 1.387(2) . ?
N1 C14 1.423(2) . ?
N2 C13 1.142(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.371(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.437(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.408(2) . ?
C8 C9 1.359(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.401(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.384(2) . ?
C10 C13 1.425(3) . ?
C11 C12 1.374(2) . ?
C11 H11A 0.9300 . ?
C14 C19 1.373(3) . ?
C14 C15 1.375(2) . ?
C15 C16 1.377(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.360(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.365(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.386(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 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
C12 N1 C1 108.49(13) . . ?
C12 N1 C14 126.24(15) . . ?
C1 N1 C14 124.37(14) . . ?
C2 C1 N1 129.61(15) . . ?
C2 C1 C6 121.31(17) . . ?
N1 C1 C6 109.09(15) . . ?
C3 C2 C1 118.30(17) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 121.21(18) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.58(18) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.76(17) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C1 118.84(17) . . ?
C5 C6 C7 134.46(16) . . ?
C1 C6 C7 106.70(15) . . ?
C8 C7 C12 118.92(17) . . ?
C8 C7 C6 134.08(17) . . ?
C12 C7 C6 106.97(14) . . ?
C9 C8 C7 119.91(18) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.55(17) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C11 C10 C9 120.92(18) . . ?
C11 C10 C13 119.46(18) . . ?
C9 C10 C13 119.60(17) . . ?
C12 C11 C10 117.87(17) . . ?
C12 C11 H11A 121.1 . . ?
C10 C11 H11A 121.1 . . ?
C11 C12 N1 129.40(16) . . ?
C11 C12 C7 121.83(16) . . ?
N1 C12 C7 108.74(15) . . ?
N2 C13 C10 178.1(2) . . ?
C19 C14 C15 120.46(17) . . ?
C19 C14 N1 119.72(17) . . ?
C15 C14 N1 119.80(17) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C14 C19 C18 119.1(2) . . ?
C14 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1918561'
loop_
_audit_author_name
_audit_author_address
'Yanhui Wang'
;Qingdao university of science and technology
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-(9H-carbazol-9-yl)benzonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P21/c   '

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

_cell_length_a                   10.2050(3)
_cell_length_b                   15.8800(5)
_cell_length_c                   8.5080(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.80(4)
_cell_angle_gamma                90.00
_cell_volume                     1377.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    332
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      13.15

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6921
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.1561
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2444
_reflns_number_gt                853
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0050P)²+0.0030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2444
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2031
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7460(3) 0.3247(2) 0.2405(4) 0.0688(10) Uani 1 1 d . . .
N2 N 0.6438(3) -0.0218(3) 0.4112(5) 0.1012(14) Uani 1 1 d . . .
C1 C 0.7490(4) 0.4020(3) 0.3154(5) 0.0667(11) Uani 1 1 d . . .
C2 C 0.6629(4) 0.4323(3) 0.4196(6) 0.0867(14) Uani 1 1 d . . .
H2A H 0.5887 0.4019 0.4439 0.104 Uiso 1 1 calc R . .
C3 C 0.6894(5) 0.5090(4) 0.4872(6) 0.1021(17) Uani 1 1 d . . .
H3A H 0.6328 0.5314 0.5586 0.123 Uiso 1 1 calc R . .
C4 C 0.7985(6) 0.5527(3) 0.4501(7) 0.1069(18) Uani 1 1 d . . .
H4A H 0.8153 0.6047 0.4972 0.128 Uiso 1 1 calc R . .
C5 C 0.8838(4) 0.5219(3) 0.3456(7) 0.0910(16) Uani 1 1 d . . .
H5A H 0.9567 0.5531 0.3191 0.109 Uiso 1 1 calc R . .
C6 C 0.8599(4) 0.4444(3) 0.2805(5) 0.0689(12) Uani 1 1 d . . .
C7 C 0.9302(4) 0.3919(3) 0.1799(5) 0.0717(12) Uani 1 1 d . . .
C8 C 1.0469(4) 0.3996(3) 0.1072(7) 0.0978(16) Uani 1 1 d . . .
H8A H 1.0961 0.4487 0.1188 0.117 Uiso 1 1 calc R . .
C9 C 1.0897(5) 0.3357(4) 0.0191(7) 0.1039(17) Uani 1 1 d . . .
H9A H 1.1688 0.3410 -0.0298 0.125 Uiso 1 1 calc R . .
C10 C 1.0180(5) 0.2628(3) 0.0003(6) 0.0904(15) Uani 1 1 d . . .
H10A H 1.0491 0.2198 -0.0620 0.108 Uiso 1 1 calc R . .
C11 C 0.9013(4) 0.2523(3) 0.0717(6) 0.0766(13) Uani 1 1 d . . .
H11A H 0.8530 0.2028 0.0601 0.092 Uiso 1 1 calc R . .
C12 C 0.8594(4) 0.3178(3) 0.1605(5) 0.0680(12) Uani 1 1 d . . .
C13 C 0.6475(4) 0.2639(3) 0.2542(5) 0.0674(12) Uani 1 1 d . . .
C14 C 0.5177(4) 0.2850(3) 0.2184(6) 0.0875(15) Uani 1 1 d . . .
H14A H 0.4955 0.3383 0.1804 0.105 Uiso 1 1 calc R . .
C15 C 0.4234(4) 0.2260(3) 0.2402(6) 0.0928(16) Uani 1 1 d . . .
H15A H 0.3360 0.2403 0.2193 0.111 Uiso 1 1 calc R . .
C16 C 0.4528(4) 0.1467(3) 0.2915(5) 0.0821(14) Uani 1 1 d . . .
H16A H 0.3869 0.1075 0.3064 0.099 Uiso 1 1 calc R . .
C17 C 0.5832(4) 0.1261(2) 0.3210(5) 0.0652(11) Uani 1 1 d . . .
C18 C 0.6800(4) 0.1842(3) 0.3026(5) 0.0642(11) Uani 1 1 d . . .
H18A H 0.7675 0.1697 0.3229 0.077 Uiso 1 1 calc R . .
C19 C 0.6151(4) 0.0440(3) 0.3723(6) 0.0780(14) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.375(5) . ?
N1 C1 1.383(5) . ?
N1 C13 1.403(4) . ?
N2 C19 1.131(5) . ?
C1 C6 1.362(5) . ?
C1 C2 1.367(5) . ?
C2 C3 1.368(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.415(5) . ?
C7 C8 1.374(5) . ?
C7 C12 1.386(5) . ?
C8 C9 1.348(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.374(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.373(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11A 0.9300 . ?
C13 C18 1.366(5) . ?
C13 C14 1.385(4) . ?
C14 C15 1.362(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.361(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.367(4) . ?
C17 C19 1.408(5) . ?
C18 H18A 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
C12 N1 C1 107.3(3) . . ?
C12 N1 C13 127.7(4) . . ?
C1 N1 C13 124.9(4) . . ?
C6 C1 C2 122.3(4) . . ?
C6 C1 N1 109.8(4) . . ?
C2 C1 N1 127.7(4) . . ?
C1 C2 C3 117.8(4) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C1 C6 C5 119.4(5) . . ?
C1 C6 C7 106.9(4) . . ?
C5 C6 C7 133.6(5) . . ?
C8 C7 C12 118.7(5) . . ?
C8 C7 C6 134.1(5) . . ?
C12 C7 C6 107.2(4) . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.9(5) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C12 C11 C10 117.0(4) . . ?
C12 C11 H11A 121.5 . . ?
C10 C11 H11A 121.5 . . ?
C11 C12 N1 128.8(4) . . ?
C11 C12 C7 122.4(4) . . ?
N1 C12 C7 108.7(4) . . ?
C18 C13 C14 120.4(4) . . ?
C18 C13 N1 119.8(4) . . ?
C14 C13 N1 119.8(4) . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C16 C15 C14 122.3(4) . . ?
C16 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C15 C16 C17 118.2(4) . . ?
C15 C16 H16A 120.9 . . ?
C17 C16 H16A 120.9 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 C19 120.2(4) . . ?
C16 C17 C19 118.8(4) . . ?
C13 C18 C17 119.5(4) . . ?
C13 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
N2 C19 C17 178.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1918562'
loop_
_audit_author_name
_audit_author_address
'Yanhui Wang'
;Qingdao university of science and technology
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        2-(9H-carbazol-9-yl)benzonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31

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'
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           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   14.7314(14)
_cell_length_b                   24.585(2)
_cell_length_c                   8.0451(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2913.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2721
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.74

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8583
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.765
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3248
_reflns_number_gt                2507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.991

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0731P)²] 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 886 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_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
C1 C 0.5921(2) 0.21050(13) 0.4259(6) 0.0923(12) Uani 1 1 d . . . . .
H1A H 0.565503 0.176623 0.409342 0.111 Uiso 1 1 calc R U . . .
C2 C 0.6516(3) 0.21717(13) 0.5549(6) 0.0866(11) Uani 1 1 d . . . . .
H2A H 0.665286 0.187580 0.622366 0.104 Uiso 1 1 calc R U . . .
C3 C 0.69194(19) 0.26701(11) 0.5874(5) 0.0688(8) Uani 1 1 d . . . . .
H3A H 0.732215 0.271603 0.675279 0.083 Uiso 1 1 calc R U . . .
C4 C 0.66946(15) 0.30949(9) 0.4829(4) 0.0512(6) Uani 1 1 d . . . . .
C5 C 0.61022(16) 0.30309(10) 0.3478(4) 0.0552(7) Uani 1 1 d . . . . .
C6 C 0.57054(18) 0.25249(13) 0.3200(5) 0.0770(9) Uani 1 1 d . . . . .
H6A H 0.530482 0.247216 0.232160 0.092 Uiso 1 1 calc R U . . .
C7 C 0.65643(14) 0.39200(9) 0.3575(3) 0.0428(5) Uani 1 1 d . . . . .
C8 C 0.65993(15) 0.44702(10) 0.3203(3) 0.0467(6) Uani 1 1 d . . . . .
H8A H 0.695776 0.470799 0.381734 0.056 Uiso 1 1 calc R U . . .
C9 C 0.60809(17) 0.46513(12) 0.1884(3) 0.0569(6) Uani 1 1 d . . . . .
H9A H 0.608765 0.501902 0.161354 0.068 Uiso 1 1 calc R U . . .
C10 C 0.55492(17) 0.42977(14) 0.0950(4) 0.0655(8) Uani 1 1 d . . . . .
H10A H 0.521565 0.443064 0.005709 0.079 Uiso 1 1 calc R U . . .
C11 C 0.55121(16) 0.37533(14) 0.1336(3) 0.0622(8) Uani 1 1 d . . . . .
H11A H 0.515397 0.351849 0.071003 0.075 Uiso 1 1 calc R U . . .
C12 C 0.60179(14) 0.35558(11) 0.2678(3) 0.0499(6) Uani 1 1 d . . . . .
C13 C 0.75084(15) 0.38766(9) 0.6152(3) 0.0430(5) Uani 1 1 d . . . . .
C14 C 0.71990(18) 0.38710(11) 0.7781(3) 0.0558(7) Uani 1 1 d . . . . .
H14A H 0.664708 0.370751 0.803626 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7711(2) 0.41080(12) 0.9021(3) 0.0646(8) Uani 1 1 d . . . . .
H15A H 0.750491 0.409762 1.011377 0.077 Uiso 1 1 calc R U . . .
C16 C 0.8520(2) 0.43590(12) 0.8663(4) 0.0672(8) Uani 1 1 d . . . . .
H16A H 0.885430 0.452121 0.950846 0.081 Uiso 1 1 calc R U . . .
C17 C 0.8835(2) 0.43709(12) 0.7058(4) 0.0618(7) Uani 1 1 d . . . . .
H17A H 0.938055 0.454383 0.681613 0.074 Uiso 1 1 calc R U . . .
C18 C 0.83385(16) 0.41243(10) 0.5790(3) 0.0484(6) Uani 1 1 d . . . . .
C19 C 0.86852(18) 0.41204(12) 0.4124(4) 0.0589(7) Uani 1 1 d . . . . .
N1 N 0.69913(12) 0.36364(7) 0.4864(3) 0.0466(5) Uani 1 1 d . . . . .
N2 N 0.89807(18) 0.41238(13) 0.2811(4) 0.0847(9) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.368(6) . ?
C1 C6 1.376(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3A 0.9300 . ?
C4 N1 1.401(3) . ?
C4 C5 1.403(4) . ?
C5 C6 1.392(4) . ?
C5 C12 1.448(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.386(3) . ?
C7 N1 1.399(3) . ?
C7 C12 1.404(3) . ?
C8 C9 1.381(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.390(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.399(4) . ?
C11 H11A 0.9300 . ?
C13 C14 1.388(3) . ?
C13 C18 1.397(3) . ?
C13 N1 1.415(3) . ?
C14 C15 1.380(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.394(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.435(4) . ?
C19 N2 1.142(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.8(3) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 H3A 121.6 . . ?
C2 C3 H3A 121.6 . . ?
C3 C4 N1 129.2(3) . . ?
C3 C4 C5 122.4(2) . . ?
N1 C4 C5 108.4(2) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 C12 133.6(3) . . ?
C4 C5 C12 107.3(2) . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6A 120.8 . . ?
C5 C6 H6A 120.8 . . ?
C8 C7 N1 129.0(2) . . ?
C8 C7 C12 122.2(2) . . ?
N1 C7 C12 108.7(2) . . ?
C9 C8 C7 117.4(2) . . ?
C9 C8 H8A 121.3 . . ?
C7 C8 H8A 121.3 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9A 119.2 . . ?
C10 C9 H9A 119.2 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 118.8(2) . . ?
C11 C12 C5 134.3(2) . . ?
C7 C12 C5 106.9(2) . . ?
C14 C13 C18 119.3(2) . . ?
C14 C13 N1 120.7(2) . . ?
C18 C13 N1 120.0(2) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C13 119.8(2) . . ?
C17 C18 C19 120.0(2) . . ?
C13 C18 C19 120.2(2) . . ?
N2 C19 C18 178.3(3) . . ?
C7 N1 C4 108.56(19) . . ?
C7 N1 C13 125.23(18) . . ?
C4 N1 C13 125.4(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
C6 C1 C2 C3 1.2(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 N1 179.7(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
N1 C4 C5 C6 -179.0(2) . . . . ?
C3 C4 C5 C12 179.5(2) . . . . ?
N1 C4 C5 C12 -1.3(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C12 C5 C6 C1 -177.8(3) . . . . ?
N1 C7 C8 C9 -177.6(2) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C7 -1.2(3) . . . . ?
C10 C11 C12 C5 175.9(3) . . . . ?
C8 C7 C12 C11 1.8(3) . . . . ?
N1 C7 C12 C11 179.05(19) . . . . ?
C8 C7 C12 C5 -176.0(2) . . . . ?
N1 C7 C12 C5 1.2(2) . . . . ?
C6 C5 C12 C11 0.0(5) . . . . ?
C4 C5 C12 C11 -177.3(2) . . . . ?
C6 C5 C12 C7 177.3(3) . . . . ?
C4 C5 C12 C7 0.0(3) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
N1 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C13 1.6(4) . . . . ?
C16 C17 C18 C19 -177.8(3) . . . . ?
C14 C13 C18 C17 -1.3(3) . . . . ?
N1 C13 C18 C17 178.6(2) . . . . ?
C14 C13 C18 C19 178.1(2) . . . . ?
N1 C13 C18 C19 -2.1(3) . . . . ?
C8 C7 N1 C4 175.0(2) . . . . ?
C12 C7 N1 C4 -2.0(2) . . . . ?
C8 C7 N1 C13 5.0(3) . . . . ?
C12 C7 N1 C13 -172.0(2) . . . . ?
C3 C4 N1 C7 -178.8(3) . . . . ?
C5 C4 N1 C7 2.1(2) . . . . ?
C3 C4 N1 C13 -8.9(4) . . . . ?
C5 C4 N1 C13 172.0(2) . . . . ?
C14 C13 N1 C7 112.0(2) . . . . ?
C18 C13 N1 C7 -67.8(3) . . . . ?
C14 C13 N1 C4 -56.3(3) . . . . ?
C18 C13 N1 C4 123.8(2) . . . . ?

_refine_diff_density_max         0.087
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1936260'
loop_
_audit_author_name
_audit_author_address
'Yanhui Wang'
;Qingdao university of science and technology
China
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H24 N4'
_chemical_formula_weight         536.61

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.265(8)
_cell_length_b                   8.089(4)
_cell_length_c                   22.642(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.613(11)
_cell_angle_gamma                90
_cell_volume                     2793(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3230
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      24.23

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13685
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4908
_reflns_number_gt                3278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0467P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0058(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4908
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_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
C1 C 0.62840(16) 0.2245(3) 0.35880(11) 0.0597(6) Uani 1 1 d . . . . .
H1 H 0.637153 0.129624 0.335051 0.072 Uiso 1 1 calc R U . . .
C2 C 0.68997(17) 0.2708(3) 0.40193(13) 0.0676(7) Uani 1 1 d . . . . .
H2 H 0.741954 0.207173 0.407757 0.081 Uiso 1 1 calc R U . . .
C3 C 0.67773(16) 0.4078(3) 0.43687(12) 0.0663(7) Uani 1 1 d . . . . .
H3 H 0.721326 0.436329 0.466387 0.080 Uiso 1 1 calc R U . . .
C4 C 0.60377(15) 0.5037(3) 0.42983(11) 0.0566(6) Uani 1 1 d . . . . .
H4 H 0.595118 0.597242 0.454251 0.068 Uiso 1 1 calc R U . . .
C5 C 0.54238(14) 0.4592(2) 0.38595(10) 0.0465(5) Uani 1 1 d . . . . .
C6 C 0.55297(14) 0.3202(2) 0.35084(10) 0.0476(5) Uani 1 1 d . . . . .
C7 C 0.42114(13) 0.4393(2) 0.32549(9) 0.0437(5) Uani 1 1 d . . . . .
C8 C 0.34135(14) 0.4659(2) 0.29466(10) 0.0506(6) Uani 1 1 d . . . . .
H8 H 0.304951 0.557016 0.303589 0.061 Uiso 1 1 calc R U . . .
C9 C 0.31746(16) 0.3556(3) 0.25095(10) 0.0582(6) Uani 1 1 d . . . . .
H9 H 0.263274 0.370389 0.229272 0.070 Uiso 1 1 calc R U . . .
C10 C 0.37037(17) 0.2229(3) 0.23759(11) 0.0625(7) Uani 1 1 d . . . . .
H10 H 0.351903 0.148546 0.207037 0.075 Uiso 1 1 calc R U . . .
C11 C 0.44885(17) 0.1975(3) 0.26778(11) 0.0583(6) Uani 1 1 d . . . . .
H11 H 0.484704 0.106035 0.258455 0.070 Uiso 1 1 calc R U . . .
C12 C 0.47544(14) 0.3071(2) 0.31218(9) 0.0469(5) Uani 1 1 d . . . . .
C13 C 0.43206(13) 0.6857(2) 0.39199(9) 0.0429(5) Uani 1 1 d . . . . .
C14 C 0.48688(15) 0.8207(2) 0.39478(10) 0.0517(6) Uani 1 1 d . . . . .
H14 H 0.545652 0.810354 0.383169 0.062 Uiso 1 1 calc R U . . .
C15 C 0.45724(15) 0.9697(3) 0.41418(10) 0.0537(6) Uani 1 1 d . . . . .
H15 H 0.495986 1.061491 0.417228 0.064 Uiso 1 1 calc R U . . .
C16 C 0.37130(14) 0.9871(2) 0.42933(9) 0.0469(5) Uani 1 1 d . . . . .
C17 C 0.31705(15) 0.8525(3) 0.42709(10) 0.0519(6) Uani 1 1 d . . . . .
H17 H 0.258035 0.863622 0.438111 0.062 Uiso 1 1 calc R U . . .
C18 C 0.34684(15) 0.7017(2) 0.40914(10) 0.0497(6) Uani 1 1 d . . . . .
H18 H 0.308979 0.608404 0.408492 0.060 Uiso 1 1 calc R U . . .
C19 C 0.33812(16) 1.1456(3) 0.44595(11) 0.0599(6) Uani 1 1 d . . . . .
C20 C 0.09046(15) -0.3040(2) 0.25280(9) 0.0487(6) Uani 1 1 d . . . . .
H20 H 0.058395 -0.396537 0.237590 0.058 Uiso 1 1 calc R U . . .
C21 C 0.17101(16) -0.2659(3) 0.23216(10) 0.0532(6) Uani 1 1 d . . . . .
H21 H 0.194386 -0.331353 0.201797 0.064 Uiso 1 1 calc R U . . .
C22 C 0.21880(15) -0.1331(3) 0.25505(9) 0.0515(6) Uani 1 1 d . . . . .
H22 H 0.275396 -0.111697 0.241008 0.062 Uiso 1 1 calc R U . . .
C23 C 0.18636(14) -0.0312(2) 0.29762(9) 0.0451(5) Uani 1 1 d . . . . .
H23 H 0.219334 0.059961 0.313016 0.054 Uiso 1 1 calc R U . . .
C24 C 0.10420(13) -0.0667(2) 0.31698(8) 0.0389(5) Uani 1 1 d . . . . .
C25 C 0.05653(14) -0.2049(2) 0.29639(9) 0.0406(5) Uani 1 1 d . . . . .
C26 C -0.02121(13) -0.0747(2) 0.36599(8) 0.0384(5) Uani 1 1 d . . . . .
C27 C -0.09102(13) -0.0398(2) 0.40087(9) 0.0439(5) Uani 1 1 d . . . . .
H27 H -0.091667 0.056715 0.424769 0.053 Uiso 1 1 calc R U . . .
C28 C -0.15941(15) -0.1506(3) 0.39949(9) 0.0510(6) Uani 1 1 d . . . . .
H28 H -0.208224 -0.129996 0.422998 0.061 Uiso 1 1 calc R U . . .
C29 C -0.15894(15) -0.2918(3) 0.36457(10) 0.0544(6) Uani 1 1 d . . . . .
H29 H -0.206471 -0.367519 0.365346 0.065 Uiso 1 1 calc R U . . .
C30 C -0.09081(15) -0.3228(2) 0.32918(9) 0.0497(6) Uani 1 1 d . . . . .
H30 H -0.090719 -0.419317 0.305255 0.060 Uiso 1 1 calc R U . . .
C31 C -0.02204(14) -0.2121(2) 0.32860(9) 0.0396(5) Uani 1 1 d . . . . .
C32 C 0.07687(12) 0.1671(2) 0.38574(8) 0.0369(5) Uani 1 1 d . . . . .
C33 C 0.10247(13) 0.2985(2) 0.35167(9) 0.0421(5) Uani 1 1 d . . . . .
H33 H 0.109178 0.284105 0.310483 0.051 Uiso 1 1 calc R U . . .
C34 C 0.11817(13) 0.4492(2) 0.37724(9) 0.0429(5) Uani 1 1 d . . . . .
H34 H 0.137049 0.539002 0.353935 0.051 Uiso 1 1 calc R U . . .
C35 C 0.10667(12) 0.4716(2) 0.43688(9) 0.0375(5) Uani 1 1 d . . . . .
C36 C 0.08314(12) 0.3395(2) 0.47141(9) 0.0406(5) Uani 1 1 d . . . . .
H36 H 0.076453 0.353887 0.512606 0.049 Uiso 1 1 calc R U . . .
C37 C 0.06950(13) 0.1875(2) 0.44579(8) 0.0399(5) Uani 1 1 d . . . . .
H37 H 0.054877 0.095647 0.469566 0.048 Uiso 1 1 calc R U . . .
C38 C 0.11733(13) 0.6328(2) 0.46267(9) 0.0429(5) Uani 1 1 d . . . . .
N1 N 0.46177(11) 0.53239(19) 0.37052(8) 0.0466(4) Uani 1 1 d . . . . .
N2 N 0.31165(15) 1.2716(3) 0.45844(12) 0.0851(8) Uani 1 1 d . . . . .
N3 N 0.05611(10) 0.01343(17) 0.35924(7) 0.0391(4) Uani 1 1 d . . . . .
N4 N 0.12390(12) 0.7616(2) 0.48295(9) 0.0571(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(3) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 N1 1.395(3) . ?
C6 C12 1.443(3) . ?
C7 N1 1.390(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.376(3) . ?
C13 C18 1.381(3) . ?
C13 N1 1.414(2) . ?
C14 C15 1.367(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(3) . ?
C16 C19 1.435(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.137(3) . ?
C20 C21 1.370(3) . ?
C20 C25 1.390(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 N3 1.392(2) . ?
C24 C25 1.402(3) . ?
C25 C31 1.433(3) . ?
C26 C27 1.384(3) . ?
C26 N3 1.393(2) . ?
C26 C31 1.397(3) . ?
C27 C28 1.375(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.365(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C32 C37 1.379(3) . ?
C32 C33 1.380(3) . ?
C32 N3 1.410(2) . ?
C33 C34 1.367(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(3) . ?
C35 C38 1.435(3) . ?
C36 C37 1.372(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 N4 1.140(2) . ?

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 C1 C6 118.3(2) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 N1 129.11(19) . . ?
C6 C5 N1 108.91(18) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C12 107.00(18) . . ?
C1 C6 C12 133.5(2) . . ?
N1 C7 C8 129.38(19) . . ?
N1 C7 C12 108.92(18) . . ?
C8 C7 C12 121.7(2) . . ?
C9 C8 C7 117.3(2) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 C6 133.7(2) . . ?
C7 C12 C6 106.95(18) . . ?
C14 C13 C18 119.46(19) . . ?
C14 C13 N1 120.53(19) . . ?
C18 C13 N1 120.00(18) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.39(19) . . ?
C17 C16 C19 120.1(2) . . ?
C15 C16 C19 120.53(19) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.78(19) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
N2 C19 C16 179.2(3) . . ?
C21 C20 C25 118.79(19) . . ?
C21 C20 H20 120.6 . . ?
C25 C20 H20 120.6 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 121.7(2) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 117.4(2) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
C23 C24 N3 129.62(18) . . ?
C23 C24 C25 121.78(19) . . ?
N3 C24 C25 108.54(18) . . ?
C20 C25 C24 119.4(2) . . ?
C20 C25 C31 133.29(18) . . ?
C24 C25 C31 107.26(17) . . ?
C27 C26 N3 129.54(18) . . ?
C27 C26 C31 121.47(19) . . ?
N3 C26 C31 108.95(18) . . ?
C28 C27 C26 117.2(2) . . ?
C28 C27 H27 121.4 . . ?
C26 C27 H27 121.4 . . ?
C27 C28 C29 121.7(2) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.1(2) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C30 C31 C26 119.8(2) . . ?
C30 C31 C25 133.28(19) . . ?
C26 C31 C25 106.95(17) . . ?
C37 C32 C33 119.77(17) . . ?
C37 C32 N3 119.89(16) . . ?
C33 C32 N3 120.32(17) . . ?
C34 C33 C32 119.94(19) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.21(18) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C36 120.02(17) . . ?
C34 C35 C38 119.95(17) . . ?
C36 C35 C38 120.02(18) . . ?
C37 C36 C35 119.50(18) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C32 120.44(17) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
N4 C38 C35 178.5(2) . . ?
C7 N1 C5 108.22(16) . . ?
C7 N1 C13 125.98(17) . . ?
C5 N1 C13 125.37(17) . . ?
C24 N3 C26 108.25(15) . . ?
C24 N3 C32 125.99(17) . . ?
C26 N3 C32 125.40(16) . . ?

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
C6 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C3 C4 C5 N1 178.5(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
N1 C5 C6 C1 -179.01(19) . . . . ?
C4 C5 C6 C12 177.3(2) . . . . ?
N1 C5 C6 C12 -0.1(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C12 -178.0(2) . . . . ?
N1 C7 C8 C9 178.6(2) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C10 C11 C12 C6 -178.1(2) . . . . ?
N1 C7 C12 C11 -179.24(19) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
N1 C7 C12 C6 -0.1(2) . . . . ?
C8 C7 C12 C6 178.08(19) . . . . ?
C5 C6 C12 C11 179.1(2) . . . . ?
C1 C6 C12 C11 -2.2(4) . . . . ?
C5 C6 C12 C7 0.1(2) . . . . ?
C1 C6 C12 C7 178.8(2) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
N1 C13 C14 C15 178.4(2) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C14 C15 C16 C17 2.7(3) . . . . ?
C14 C15 C16 C19 -175.8(2) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C19 C16 C17 C18 177.5(2) . . . . ?
C16 C17 C18 C13 -1.3(3) . . . . ?
C14 C13 C18 C17 1.9(3) . . . . ?
N1 C13 C18 C17 -176.72(19) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C20 C21 C22 C23 -2.3(3) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 N3 179.58(18) . . . . ?
C22 C23 C24 C25 2.7(3) . . . . ?
C21 C20 C25 C24 1.6(3) . . . . ?
C21 C20 C25 C31 -177.5(2) . . . . ?
C23 C24 C25 C20 -3.7(3) . . . . ?
N3 C24 C25 C20 178.84(16) . . . . ?
C23 C24 C25 C31 175.57(17) . . . . ?
N3 C24 C25 C31 -1.9(2) . . . . ?
N3 C26 C27 C28 -179.28(17) . . . . ?
C31 C26 C27 C28 3.2(3) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C30 -1.6(3) . . . . ?
C28 C29 C30 C31 0.2(3) . . . . ?
C29 C30 C31 C26 2.9(3) . . . . ?
C29 C30 C31 C25 -178.2(2) . . . . ?
C27 C26 C31 C30 -4.7(3) . . . . ?
N3 C26 C31 C30 177.35(16) . . . . ?
C27 C26 C31 C25 176.12(17) . . . . ?
N3 C26 C31 C25 -1.85(19) . . . . ?
C20 C25 C31 C30 2.4(4) . . . . ?
C24 C25 C31 C30 -176.8(2) . . . . ?
C20 C25 C31 C26 -178.6(2) . . . . ?
C24 C25 C31 C26 2.27(19) . . . . ?
C37 C32 C33 C34 -1.7(3) . . . . ?
N3 C32 C33 C34 176.68(17) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
C33 C34 C35 C36 3.0(3) . . . . ?
C33 C34 C35 C38 -175.67(18) . . . . ?
C34 C35 C36 C37 -1.4(3) . . . . ?
C38 C35 C36 C37 177.24(18) . . . . ?
C35 C36 C37 C32 -1.7(3) . . . . ?
C33 C32 C37 C36 3.3(3) . . . . ?
N3 C32 C37 C36 -175.11(17) . . . . ?
C8 C7 N1 C5 -178.0(2) . . . . ?
C12 C7 N1 C5 0.1(2) . . . . ?
C8 C7 N1 C13 -5.2(3) . . . . ?
C12 C7 N1 C13 172.85(18) . . . . ?
C4 C5 N1 C7 -177.1(2) . . . . ?
C6 C5 N1 C7 0.0(2) . . . . ?
C4 C5 N1 C13 10.0(3) . . . . ?
C6 C5 N1 C13 -172.82(18) . . . . ?
C14 C13 N1 C7 -126.6(2) . . . . ?
C18 C13 N1 C7 52.0(3) . . . . ?
C14 C13 N1 C5 45.0(3) . . . . ?
C18 C13 N1 C5 -136.4(2) . . . . ?
C23 C24 N3 C26 -176.43(18) . . . . ?
C25 C24 N3 C26 0.74(19) . . . . ?
C23 C24 N3 C32 10.2(3) . . . . ?
C25 C24 N3 C32 -172.60(16) . . . . ?
C27 C26 N3 C24 -177.03(19) . . . . ?
C31 C26 N3 C24 0.71(19) . . . . ?
C27 C26 N3 C32 -3.6(3) . . . . ?
C31 C26 N3 C32 174.11(16) . . . . ?
C37 C32 N3 C24 -136.58(19) . . . . ?
C33 C32 N3 C24 45.0(3) . . . . ?
C37 C32 N3 C26 51.2(2) . . . . ?
C33 C32 N3 C26 -127.2(2) . . . . ?

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
C4 H4 N2 0.95 2.61 3.327(3) 132.8 3_676
C27 H27 N4 0.95 2.62 3.515(3) 157.3 3_566

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1918555'
loop_
_audit_author_name
_audit_author_address
'Yanhui Wang'
;Qingdao university of science and technology
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        9-phenyl-9H-carbazole-3-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   13.648(3)
_cell_length_b                   10.5450(10)
_cell_length_c                   18.9249(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.28(3)
_cell_angle_gamma                90.00
_cell_volume                     2721.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1909
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      24.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6431
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2387
_reflns_number_gt                1652
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+2.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2387
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.16160(10) -0.05079(16) 0.18736(8) 0.0517(6) Uani 1 1 d G . .
C10 C 0.23580(13) -0.12909(16) 0.16432(8) 0.0625(7) Uani 1 1 d G . .
H10A H 0.2266 -0.1750 0.1226 0.075 Uiso 1 1 calc R . .
C11 C 0.32372(11) -0.13876(18) 0.20361(10) 0.0749(9) Uani 1 1 d G . .
H11A H 0.3734 -0.1911 0.1882 0.090 Uiso 1 1 calc R . .
C12 C 0.33745(11) -0.0701(2) 0.26592(10) 0.0736(9) Uani 1 1 d G . .
H12A H 0.3963 -0.0766 0.2922 0.088 Uiso 1 1 calc R . .
C13 C 0.26325(15) 0.00818(18) 0.28895(7) 0.0777(9) Uani 1 1 d G . .
H13A H 0.2724 0.0541 0.3306 0.093 Uiso 1 1 calc R . .
C14 C 0.17533(12) 0.01784(17) 0.24967(8) 0.0641(7) Uani 1 1 d G . .
H14A H 0.1257 0.0702 0.2651 0.077 Uiso 1 1 calc R . .
N1 N 0.07305(14) -0.04021(19) 0.14791(10) 0.0531(5) Uani 1 1 d . . .
N2 N -0.15118(19) 0.4314(2) -0.02725(14) 0.0785(8) Uani 1 1 d . . .
C1 C 0.00662(18) -0.1378(2) 0.13466(12) 0.0522(6) Uani 1 1 d . . .
C2 C 0.0113(2) -0.2617(3) 0.15681(14) 0.0625(7) Uani 1 1 d . . .
H2A H 0.0639 -0.2918 0.1847 0.075 Uiso 1 1 calc R . .
C3 C -0.0651(2) -0.3391(3) 0.13595(15) 0.0706(8) Uani 1 1 d . . .
H3A H -0.0636 -0.4239 0.1495 0.085 Uiso 1 1 calc R . .
C4 C -0.1441(2) -0.2948(3) 0.09552(16) 0.0711(8) Uani 1 1 d . . .
H4A H -0.1948 -0.3501 0.0825 0.085 Uiso 1 1 calc R . .
C5 C -0.1491(2) -0.1712(3) 0.07432(14) 0.0614(7) Uani 1 1 d . . .
H5A H -0.2028 -0.1416 0.0474 0.074 Uiso 1 1 calc R . .
C6 C -0.07274(17) -0.0908(2) 0.09377(12) 0.0498(6) Uani 1 1 d . . .
C7 C -0.05283(17) 0.0406(2) 0.08115(12) 0.0481(6) Uani 1 1 d . . .
C8 C 0.03781(17) 0.0684(2) 0.11567(12) 0.0477(6) Uani 1 1 d . . .
C15 C 0.07939(19) 0.1875(2) 0.11325(13) 0.0553(7) Uani 1 1 d . . .
H15A H 0.1390 0.2047 0.1368 0.066 Uiso 1 1 calc R . .
C16 C 0.03049(18) 0.2795(2) 0.07523(13) 0.0558(7) Uani 1 1 d . . .
H16A H 0.0576 0.3602 0.0723 0.067 Uiso 1 1 calc R . .
C17 C -0.05930(18) 0.2543(2) 0.04076(12) 0.0520(6) Uani 1 1 d . . .
C18 C -0.10143(18) 0.1353(2) 0.04370(12) 0.0538(6) Uani 1 1 d . . .
H18A H -0.1617 0.1193 0.0207 0.065 Uiso 1 1 calc R . .
C19 C -0.1097(2) 0.3530(3) 0.00248(14) 0.0603(7) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C9 N1 1.400(2) . ?
C10 C11 1.3900 . ?
C10 H10A 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11A 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12A 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
N1 C8 1.376(3) . ?
N1 C1 1.388(3) . ?
N2 C19 1.138(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.397(3) . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.434(3) . ?
C7 C18 1.379(3) . ?
C7 C8 1.407(3) . ?
C8 C15 1.379(3) . ?
C15 C16 1.366(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.391(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.383(3) . ?
C17 C19 1.429(4) . ?
C18 H18A 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
C10 C9 C14 120.0 . . ?
C10 C9 N1 120.30(14) . . ?
C14 C9 N1 119.70(14) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C9 C14 H14A 120.0 . . ?
C8 N1 C1 108.85(19) . . ?
C8 N1 C9 125.61(19) . . ?
C1 N1 C9 125.54(19) . . ?
C2 C1 N1 128.9(2) . . ?
C2 C1 C6 122.2(2) . . ?
N1 C1 C6 108.9(2) . . ?
C3 C2 C1 116.9(3) . . ?
C3 C2 H2A 121.5 . . ?
C1 C2 H2A 121.5 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 133.9(2) . . ?
C1 C6 C7 106.7(2) . . ?
C18 C7 C8 118.9(2) . . ?
C18 C7 C6 134.0(2) . . ?
C8 C7 C6 107.1(2) . . ?
N1 C8 C15 129.5(2) . . ?
N1 C8 C7 108.5(2) . . ?
C15 C8 C7 122.0(2) . . ?
C16 C15 C8 118.1(2) . . ?
C16 C15 H15A 121.0 . . ?
C8 C15 H15A 121.0 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 C19 119.3(2) . . ?
C16 C17 C19 119.8(2) . . ?
C7 C18 C17 119.1(2) . . ?
C7 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
N2 C19 C17 178.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
