#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:29:48 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268675 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/31/7243189.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_7243189
loop_
_publ_author_name
'Wang, Si-Si'
'Li, Kechang'
'Ma, Xiaohui'
'Xue, Pengchong'
_publ_section_title
;
 Acceptor-regulated luminescence in carbazole-based charge transfer
 complexes
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5314
_journal_page_last               5320
_journal_paper_doi               10.1039/D1CE00656H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C24 H14 N5'
_chemical_formula_weight         372.40
_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-2013
_audit_update_record
;
2021-03-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.538(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.694(5)
_cell_length_b                   7.226(2)
_cell_length_c                   17.313(5)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.74
_cell_measurement_theta_min      2.59
_cell_volume                     1954.2(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_min         1.304
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             772
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/n-haxane'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.986
_exptl_transmission_factor_min   0.983
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0477
_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)+(0.0647P)²+0.0140P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2458
_reflns_number_total             4041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00656h2.cif
_cod_data_source_block           n201222a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'NONE' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243188--7243189.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243189
_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   0.983
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-2
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
N1 N 0.35717(10) 0.1680(2) 0.43431(9) 0.0431(4) Uani 1 1 d . . . . .
N2 N 0.42750(13) 0.5941(3) 0.32972(13) 0.0735(6) Uani 1 1 d . . . . .
N3 N 0.34553(13) 0.7015(3) 0.53810(11) 0.0682(6) Uani 1 1 d . . . . .
N4 N -0.05657(13) 0.4089(3) 0.40105(12) 0.0769(6) Uani 1 1 d . . . . .
N5 N 0.01686(14) 0.3286(3) 0.19761(12) 0.0797(7) Uani 1 1 d . . . . .
C1 C 0.33998(12) 0.1007(2) 0.35920(11) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.39301(14) 0.0885(3) 0.29961(12) 0.0544(6) Uani 1 1 d . . . . .
H2 H 0.4497 0.1272 0.3067 0.065 Uiso 1 1 calc R U . . .
C3 C 0.35882(15) 0.0173(3) 0.22997(12) 0.0628(6) Uani 1 1 d . . . . .
H3 H 0.3935 0.0060 0.1896 0.075 Uiso 1 1 calc R U . . .
C4 C 0.27364(16) -0.0385(3) 0.21814(12) 0.0627(6) Uani 1 1 d . . . . .
H4 H 0.2523 -0.0851 0.1700 0.075 Uiso 1 1 calc R U . . .
C5 C 0.22078(14) -0.0257(3) 0.27652(12) 0.0520(6) Uani 1 1 d . . . . .
H5 H 0.1639 -0.0627 0.2682 0.062 Uiso 1 1 calc R U . . .
C6 C 0.25353(12) 0.0437(2) 0.34859(11) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.21781(12) 0.0769(2) 0.42071(11) 0.0402(5) Uani 1 1 d . . . . .
C8 C 0.13696(13) 0.0525(3) 0.44580(13) 0.0516(5) Uani 1 1 d . . . . .
H8 H 0.0928 0.0007 0.4131 0.062 Uiso 1 1 calc R U . . .
C9 C 0.12334(15) 0.1066(3) 0.52010(13) 0.0617(6) Uani 1 1 d . . . . .
H9 H 0.0696 0.0909 0.5376 0.074 Uiso 1 1 calc R U . . .
C10 C 0.18938(15) 0.1844(3) 0.56916(12) 0.0592(6) Uani 1 1 d . . . . .
H10 H 0.1784 0.2223 0.6186 0.071 Uiso 1 1 calc R U . . .
C11 C 0.27028(14) 0.2068(3) 0.54656(11) 0.0499(5) Uani 1 1 d . . . . .
H11 H 0.3144 0.2558 0.5801 0.060 Uiso 1 1 calc R U . . .
C12 C 0.28362(12) 0.1534(2) 0.47178(11) 0.0398(5) Uani 1 1 d . . . . .
C13 C 0.44000(12) 0.2294(3) 0.47135(11) 0.0485(5) Uani 1 1 d . . . . .
H13A H 0.4316 0.3383 0.5025 0.058 Uiso 1 1 calc R U . . .
H13B H 0.4764 0.2643 0.4315 0.058 Uiso 1 1 calc R U . . .
C14 C 0.48492(12) 0.0810(2) 0.52273(11) 0.0455(5) Uani 1 1 d . . . . .
H14A H 0.5338 0.1358 0.5529 0.055 Uiso 1 1 calc R U . . .
H14B H 0.4459 0.0363 0.5587 0.055 Uiso 1 1 calc R U . . .
C15 C 0.35725(14) 0.5772(3) 0.33905(12) 0.0507(5) Uani 1 1 d . . . . .
C16 C 0.26862(12) 0.5509(2) 0.35146(11) 0.0424(5) Uani 1 1 d . . . . .
C17 C 0.24049(12) 0.5883(2) 0.42387(11) 0.0415(5) Uani 1 1 d . . . . .
C18 C 0.15600(13) 0.5574(3) 0.43717(11) 0.0452(5) Uani 1 1 d . . . . .
H18 H 0.1376 0.5830 0.4855 0.054 Uiso 1 1 calc R U . . .
C19 C 0.09934(12) 0.4883(3) 0.37812(11) 0.0428(5) Uani 1 1 d . . . . .
C20 C 0.12682(12) 0.4533(3) 0.30499(11) 0.0439(5) Uani 1 1 d . . . . .
C21 C 0.21137(13) 0.4841(3) 0.29199(12) 0.0469(5) Uani 1 1 d . . . . .
H21 H 0.2297 0.4601 0.2435 0.056 Uiso 1 1 calc R U . . .
C22 C 0.29912(14) 0.6544(3) 0.48715(12) 0.0501(5) Uani 1 1 d . . . . .
C23 C 0.01230(14) 0.4463(3) 0.39151(12) 0.0540(6) Uani 1 1 d . . . . .
C24 C 0.06660(14) 0.3831(3) 0.24429(13) 0.0549(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
C12 N1 C1 108.47(15) . . ?
C12 N1 C13 124.41(16) . . ?
C1 N1 C13 126.91(17) . . ?
C2 C1 N1 129.84(19) . . ?
C2 C1 C6 121.43(18) . . ?
N1 C1 C6 108.71(17) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.14(19) . . ?
C5 C6 C7 134.07(19) . . ?
C1 C6 C7 106.78(16) . . ?
C8 C7 C12 119.34(18) . . ?
C8 C7 C6 133.94(18) . . ?
C12 C7 C6 106.70(16) . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.42(19) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C11 128.72(18) . . ?
N1 C12 C7 109.34(16) . . ?
C11 C12 C7 121.91(18) . . ?
N1 C13 C14 112.62(16) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C14 C13 113.1(2) 3_656 . ?
C14 C14 H14A 109.0 3_656 . ?
C13 C14 H14A 109.0 . . ?
C14 C14 H14B 109.0 3_656 . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C16 178.5(2) . . ?
C21 C16 C17 119.75(18) . . ?
C21 C16 C15 120.08(19) . . ?
C17 C16 C15 120.15(18) . . ?
C18 C17 C16 120.59(18) . . ?
C18 C17 C22 118.54(18) . . ?
C16 C17 C22 120.84(18) . . ?
C19 C18 C17 119.54(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.15(18) . . ?
C18 C19 C23 120.64(18) . . ?
C20 C19 C23 119.18(18) . . ?
C21 C20 C19 120.10(18) . . ?
C21 C20 C24 120.73(18) . . ?
C19 C20 C24 119.16(18) . . ?
C20 C21 C16 119.85(19) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
N3 C22 C17 178.0(2) . . ?
N4 C23 C19 178.2(3) . . ?
N5 C24 C20 177.9(2) . . ?
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 1.382(2) . ?
N1 C1 1.390(2) . ?
N1 C13 1.462(2) . ?
N2 C15 1.136(3) . ?
N3 C22 1.140(2) . ?
N4 C23 1.142(3) . ?
N5 C24 1.138(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.406(3) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C14 1.512(4) 3_656 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.440(3) . ?
C16 C21 1.386(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.442(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(3) . ?
C19 C23 1.440(3) . ?
C20 C21 1.385(3) . ?
C20 C24 1.436(3) . ?
C21 H21 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
C12 N1 C1 C2 179.27(18) . . . . ?
C13 N1 C1 C2 -5.8(3) . . . . ?
C12 N1 C1 C6 0.57(19) . . . . ?
C13 N1 C1 C6 175.51(16) . . . . ?
N1 C1 C2 C3 -179.20(18) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C5 178.63(16) . . . . ?
C2 C1 C6 C7 -179.39(17) . . . . ?
N1 C1 C6 C7 -0.56(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C1 C6 C7 C8 178.9(2) . . . . ?
C5 C6 C7 C12 -178.7(2) . . . . ?
C1 C6 C7 C12 0.34(19) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.6(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C1 N1 C12 C11 -178.51(18) . . . . ?
C13 N1 C12 C11 6.4(3) . . . . ?
C1 N1 C12 C7 -0.3(2) . . . . ?
C13 N1 C12 C7 -175.45(16) . . . . ?
C10 C11 C12 N1 177.18(18) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C8 C7 C12 N1 -178.81(16) . . . . ?
C6 C7 C12 N1 0.0(2) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C6 C7 C12 C11 178.31(17) . . . . ?
C12 N1 C13 C14 75.9(2) . . . . ?
C1 N1 C13 C14 -98.2(2) . . . . ?
N1 C13 C14 C14 69.0(3) . . . 3_656 ?
C21 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 C18 -177.76(17) . . . . ?
C21 C16 C17 C22 178.75(17) . . . . ?
C15 C16 C17 C22 0.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C22 C17 C18 C19 -177.88(17) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C17 C18 C19 C23 176.91(18) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C23 C19 C20 C21 -176.83(18) . . . . ?
C18 C19 C20 C24 -179.43(18) . . . . ?
C23 C19 C20 C24 2.4(3) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C24 C20 C21 C16 -179.63(18) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C15 C16 C21 C20 177.86(18) . . . . ?
