#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:36:16 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263733 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242277.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242277
loop_
_publ_author_name
'Chen, Pengfei'
'Yin, Yuanye'
'Ni, Yingyong'
'Zhu, Huichao'
'Huang, Jianyan'
'Yang, Jiaxiang'
'Yang, Jianjun'
'Kong, Lin'
_publ_section_title
;
 Molecular engineering of carbazole--acrylonitrile fluorophores:
 substituent-dependent optical properties and mechanochromism
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2289
_journal_page_last               2296
_journal_paper_doi               10.1039/D1CE00012H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C28 H23 N3'
_chemical_formula_weight         401.49
_chemical_name_common            kzben
_chemical_name_systematic        kzben
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-03-31 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9068(15)
_cell_length_b                   13.0177(13)
_cell_length_c                   12.5244(13)
_cell_measurement_reflns_used    6603
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.32
_cell_volume                     2303.3(4)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16109
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.441
_exptl_absorpt_coefficient_mu    0.069
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       bulk
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0036(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0470
_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)+(0.0771P)²+0.5438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3254
_reflns_number_total             4068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00012h2.cif
_cod_data_source_block           kzben
_cod_depositor_comments
'Adding full bibliography for 7242273--7242277.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242277
_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.
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
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'
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 0.08999(11) 0.54466(13) 0.19872(15) 0.0547(4) Uani 1 1 d . . . . .
C6 C 0.06679(12) 0.60675(13) 0.10191(16) 0.0598(5) Uani 1 1 d . . . . .
C2 C 0.04585(13) 0.56021(16) 0.28029(17) 0.0665(5) Uani 1 1 d . . . . .
H2 H 0.0604 0.5194 0.3445 0.080 Uiso 1 1 calc R U . . .
C5 C 0.00069(15) 0.68560(17) 0.0851(2) 0.0802(6) Uani 1 1 d . . . . .
H5 H -0.0144 0.7271 0.0214 0.096 Uiso 1 1 calc R U . . .
C4 C -0.04132(16) 0.69921(19) 0.1671(2) 0.0929(8) Uani 1 1 d . . . . .
H4 H -0.0857 0.7514 0.1581 0.111 Uiso 1 1 calc R U . . .
C3 C -0.02029(15) 0.63846(19) 0.2625(2) 0.0844(7) Uani 1 1 d . . . . .
H3 H -0.0509 0.6503 0.3154 0.101 Uiso 1 1 calc R U . . .
C10 C 0.11239(15) 0.61826(15) -0.07682(16) 0.0706(5) Uani 1 1 d . . . . .
H10A H 0.0526 0.6543 -0.1066 0.085 Uiso 1 1 calc R U . . .
H10B H 0.1123 0.5624 -0.1281 0.085 Uiso 1 1 calc R U . . .
C9 C 0.19093(17) 0.69098(17) -0.07537(19) 0.0823(6) Uani 1 1 d . . . . .
H9A H 0.2498 0.6527 -0.0547 0.099 Uiso 1 1 calc R U . . .
H9B H 0.1796 0.7169 -0.1512 0.099 Uiso 1 1 calc R U . . .
C7 C 0.2801(2) 0.8547(2) -0.0101(3) 0.1167(10) Uani 1 1 d . . . . .
H7A H 0.2802 0.9155 0.0333 0.175 Uiso 1 1 calc R U . . .
H7B H 0.2667 0.8729 -0.0879 0.175 Uiso 1 1 calc R U . . .
H7C H 0.3410 0.8221 0.0169 0.175 Uiso 1 1 calc R U . . .
C8 C 0.20298(17) 0.77943(18) 0.0018(2) 0.0866(7) Uani 1 1 d . . . . .
H8A H 0.2206 0.7548 0.0788 0.104 Uiso 1 1 calc R U . . .
H8B H 0.1433 0.8157 -0.0145 0.104 Uiso 1 1 calc R U . . .
C11 C 0.15865(11) 0.47069(12) 0.18709(13) 0.0478(4) Uani 1 1 d . . . . .
C12 C 0.20615(11) 0.38963(12) 0.25293(13) 0.0476(4) Uani 1 1 d . . . . .
H12 H 0.1990 0.3769 0.3228 0.057 Uiso 1 1 calc R U . . .
C13 C 0.17286(12) 0.49191(12) 0.08288(13) 0.0498(4) Uani 1 1 d . . . . .
C16 C 0.26473(11) 0.32742(12) 0.21327(13) 0.0478(4) Uani 1 1 d . . . . .
C15 C 0.27681(13) 0.34962(13) 0.10937(14) 0.0557(4) Uani 1 1 d . . . . .
H15 H 0.3156 0.3073 0.0833 0.067 Uiso 1 1 calc R U . . .
C14 C 0.23308(13) 0.43202(13) 0.04436(14) 0.0565(4) Uani 1 1 d . . . . .
H14 H 0.2436 0.4470 -0.0233 0.068 Uiso 1 1 calc R U . . .
C18 C 0.29197(13) 0.14066(13) 0.22898(15) 0.0566(4) Uani 1 1 d . . . . .
C19 C 0.22756(16) 0.12524(14) 0.11794(18) 0.0660(5) Uani 1 1 d . . . . .
C17 C 0.33192(15) 0.04878(14) 0.28833(17) 0.0668(5) Uani 1 1 d . . . . .
C20 C 0.31065(12) 0.23574(12) 0.27819(14) 0.0513(4) Uani 1 1 d . . . . .
C21 C 0.37400(12) 0.24472(13) 0.39249(14) 0.0546(4) Uani 1 1 d . . . . .
H21 H 0.3974 0.1840 0.4303 0.066 Uiso 1 1 calc R U . . .
C22 C 0.40188(12) 0.33241(13) 0.44841(14) 0.0531(4) Uani 1 1 d . . . . .
H22 H 0.3779 0.3929 0.4105 0.064 Uiso 1 1 calc R U . . .
C23 C 0.46627(12) 0.34271(13) 0.56311(15) 0.0554(4) Uani 1 1 d . . . . .
C28 C 0.47750(13) 0.43851(15) 0.61556(16) 0.0637(5) Uani 1 1 d . . . . .
H28 H 0.4441 0.4947 0.5766 0.076 Uiso 1 1 calc R U . . .
C27 C 0.53742(16) 0.45125(18) 0.72445(19) 0.0805(6) Uani 1 1 d . . . . .
H27 H 0.5442 0.5156 0.7585 0.097 Uiso 1 1 calc R U . . .
C24 C 0.51812(15) 0.26047(16) 0.62352(19) 0.0791(6) Uani 1 1 d . . . . .
H24 H 0.5123 0.1959 0.5902 0.095 Uiso 1 1 calc R U . . .
C26 C 0.5868(2) 0.3688(2) 0.7821(2) 0.1037(9) Uani 1 1 d . . . . .
H26 H 0.6266 0.3769 0.8557 0.124 Uiso 1 1 calc R U . . .
C25 C 0.5775(2) 0.2738(2) 0.7313(2) 0.1066(9) Uani 1 1 d . . . . .
H25 H 0.6118 0.2183 0.7705 0.128 Uiso 1 1 calc R U . . .
N1 N 0.11766(10) 0.57463(11) 0.03234(12) 0.0592(4) Uani 1 1 d . . . . .
N2 N 0.36218(17) -0.02391(14) 0.33754(19) 0.0956(6) Uani 1 1 d . . . . .
N3 N 0.17597(16) 0.10977(15) 0.02937(17) 0.0924(6) Uani 1 1 d . . . . .
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'
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 120.30(16) . . ?
C2 C1 C11 133.22(17) . . ?
C6 C1 C11 106.45(15) . . ?
N1 C6 C5 128.97(19) . . ?
N1 C6 C1 109.55(14) . . ?
C5 C6 C1 121.47(19) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C5 C6 116.8(2) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
N1 C10 C9 115.18(16) . . ?
N1 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C8 C9 C10 115.5(2) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C12 C11 C13 119.93(14) . . ?
C12 C11 C1 133.66(16) . . ?
C13 C11 C1 106.39(14) . . ?
C11 C12 C16 119.30(15) . . ?
C11 C12 H12 120.3 . . ?
C16 C12 H12 120.3 . . ?
N1 C13 C14 129.54(16) . . ?
N1 C13 C11 109.42(15) . . ?
C14 C13 C11 121.03(15) . . ?
C12 C16 C15 119.52(15) . . ?
C12 C16 C20 120.29(14) . . ?
C15 C16 C20 120.14(14) . . ?
C14 C15 C16 122.21(15) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C14 C13 117.95(15) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C20 C18 C19 122.75(16) . . ?
C20 C18 C17 121.93(16) . . ?
C19 C18 C17 115.23(16) . . ?
N3 C19 C18 178.0(2) . . ?
N2 C17 C18 178.0(2) . . ?
C18 C20 C21 119.52(15) . . ?
C18 C20 C16 119.21(15) . . ?
C21 C20 C16 121.27(14) . . ?
C22 C21 C20 125.75(15) . . ?
C22 C21 H21 117.1 . . ?
C20 C21 H21 117.1 . . ?
C21 C22 C23 126.37(15) . . ?
C21 C22 H22 116.8 . . ?
C23 C22 H22 116.8 . . ?
C28 C23 C24 117.96(17) . . ?
C28 C23 C22 119.27(16) . . ?
C24 C23 C22 122.77(17) . . ?
C27 C28 C23 121.00(19) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C26 C27 C28 119.7(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C13 N1 C6 108.19(14) . . ?
C13 N1 C10 125.40(16) . . ?
C6 N1 C10 126.40(15) . . ?
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 1.395(3) . ?
C1 C6 1.406(3) . ?
C1 C11 1.446(2) . ?
C6 N1 1.389(2) . ?
C6 C5 1.392(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.374(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.383(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C10 N1 1.459(2) . ?
C10 C9 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 C8 1.477(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C8 1.553(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C12 1.386(2) . ?
C11 C13 1.415(2) . ?
C12 C16 1.394(2) . ?
C12 H12 0.9300 . ?
C13 N1 1.380(2) . ?
C13 C14 1.387(2) . ?
C16 C15 1.400(2) . ?
C16 C20 1.483(2) . ?
C15 C14 1.378(2) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C18 C20 1.371(2) . ?
C18 C19 1.430(3) . ?
C18 C17 1.434(2) . ?
C19 N3 1.148(3) . ?
C17 N2 1.141(2) . ?
C20 C21 1.446(2) . ?
C21 C22 1.334(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.457(2) . ?
C22 H22 0.9300 . ?
C23 C28 1.394(3) . ?
C23 C24 1.394(3) . ?
C28 C27 1.381(3) . ?
C28 H28 0.9300 . ?
C27 C26 1.370(3) . ?
C27 H27 0.9300 . ?
C24 C25 1.368(3) . ?
C24 H24 0.9300 . ?
C26 C25 1.377(4) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
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
C2 C1 C6 N1 -178.26(15) . . . . ?
C11 C1 C6 N1 -0.08(18) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C11 C1 C6 C5 178.95(16) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C11 C1 C2 C3 -177.95(18) . . . . ?
N1 C6 C5 C4 178.28(19) . . . . ?
C1 C6 C5 C4 -0.5(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
N1 C10 C9 C8 -56.4(3) . . . . ?
C10 C9 C8 C7 -175.24(19) . . . . ?
C2 C1 C11 C12 -0.9(3) . . . . ?
C6 C1 C11 C12 -178.75(17) . . . . ?
C2 C1 C11 C13 177.50(18) . . . . ?
C6 C1 C11 C13 -0.33(17) . . . . ?
C13 C11 C12 C16 -2.5(2) . . . . ?
C1 C11 C12 C16 175.77(16) . . . . ?
C12 C11 C13 N1 179.32(14) . . . . ?
C1 C11 C13 N1 0.64(17) . . . . ?
C12 C11 C13 C14 0.7(2) . . . . ?
C1 C11 C13 C14 -177.95(15) . . . . ?
C11 C12 C16 C15 1.9(2) . . . . ?
C11 C12 C16 C20 -175.46(14) . . . . ?
C12 C16 C15 C14 0.5(3) . . . . ?
C20 C16 C15 C14 177.86(16) . . . . ?
C16 C15 C14 C13 -2.2(3) . . . . ?
N1 C13 C14 C15 -176.67(16) . . . . ?
C11 C13 C14 C15 1.6(3) . . . . ?
C19 C18 C20 C21 177.68(16) . . . . ?
C17 C18 C20 C21 1.3(3) . . . . ?
C19 C18 C20 C16 -1.8(3) . . . . ?
C17 C18 C20 C16 -178.16(16) . . . . ?
C12 C16 C20 C18 120.12(18) . . . . ?
C15 C16 C20 C18 -57.2(2) . . . . ?
C12 C16 C20 C21 -59.4(2) . . . . ?
C15 C16 C20 C21 123.30(18) . . . . ?
C18 C20 C21 C22 176.51(17) . . . . ?
C16 C20 C21 C22 -4.0(3) . . . . ?
C20 C21 C22 C23 -179.41(15) . . . . ?
C21 C22 C23 C28 -170.53(17) . . . . ?
C21 C22 C23 C24 9.7(3) . . . . ?
C24 C23 C28 C27 -0.7(3) . . . . ?
C22 C23 C28 C27 179.60(17) . . . . ?
C23 C28 C27 C26 0.0(3) . . . . ?
C28 C23 C24 C25 0.5(3) . . . . ?
C22 C23 C24 C25 -179.7(2) . . . . ?
C28 C27 C26 C25 0.7(4) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C27 C26 C25 C24 -0.8(5) . . . . ?
C14 C13 N1 C6 177.73(17) . . . . ?
C11 C13 N1 C6 -0.70(18) . . . . ?
C14 C13 N1 C10 -0.7(3) . . . . ?
C11 C13 N1 C10 -179.18(16) . . . . ?
C5 C6 N1 C13 -178.46(18) . . . . ?
C1 C6 N1 C13 0.48(19) . . . . ?
C5 C6 N1 C10 0.0(3) . . . . ?
C1 C6 N1 C10 178.94(16) . . . . ?
C9 C10 N1 C13 -81.5(2) . . . . ?
C9 C10 N1 C6 100.3(2) . . . . ?
