#------------------------------------------------------------------------------
#$Date: 2019-11-24 04:12:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236654 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/69/7236938.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_7236938
loop_
_publ_author_name
'Jiang, Jianxia'
'Li, Xianglong'
'Hanif, Muddasir'
'Zhou, Jiadong'
'Hu, Dehua'
'Su, Shijian'
'Xie, Zengqi'
'Gao, Yu'
'Yang, Bing'
'Ma, Yuguang'
_publ_section_title
;
 Pyridal[2,1,3]thiadiazole as strong electron-withdrawing and less
 sterically-hindered acceptor for highly efficient donor--acceptor type
 NIR materials
;
_journal_issue                   42
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              11053
_journal_paper_doi               10.1039/C7TC03978F
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C30 H19 N5 S'
_chemical_formula_sum            'C30 H19 N5 S'
_chemical_formula_weight         481.56
_chemical_name_systematic
4-(4-(4-(diphenylamino)phenyl)-[1,2,5]thiadiazolo[3,4-c]pyridin-7-yl)benzonitrile
_chemical_properties_physical    ', Efflorescent'
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 144.02(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   46.21(2)
_cell_length_b                   6.9886(10)
_cell_length_c                   24.593(13)
_cell_measurement_reflns_used    909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.5350
_cell_measurement_theta_min      7.9650
_cell_volume                     4666(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.1277
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7825
_diffrn_reflns_theta_full        67.25
_diffrn_reflns_theta_max         67.25
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    1.465
_exptl_absorpt_correction_T_max  0.9044
_exptl_absorpt_correction_T_min  0.8918
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/methanol'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.00123(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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.2366
_reflns_number_gt                1879
_reflns_number_total             4194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc03978f2.cif
_cod_data_source_block           exp_6238
_cod_original_cell_volume        4666(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7236938
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'
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
S1 S 0.82050(5) 0.0164(3) 1.20129(9) 0.0706(5) Uani 1 1 d .
N1 N 0.76548(14) 0.0513(7) 1.1391(3) 0.0595(12) Uani 1 1 d .
N2 N 0.81112(14) -0.0124(7) 1.1227(3) 0.0580(12) Uani 1 1 d .
N3 N 0.66013(14) 0.0495(6) 0.8875(3) 0.0563(12) Uani 1 1 d .
N4 N 0.56041(14) 0.2895(7) 0.9598(3) 0.0616(13) Uani 1 1 d .
N5 N 0.83747(19) -0.1651(9) 0.8534(3) 0.0903(18) Uani 1 1 d .
C1 C 0.68312(16) 0.0696(7) 0.9698(3) 0.0456(12) Uani 1 1 d .
C2 C 0.73575(17) 0.0427(7) 1.0495(3) 0.0476(12) Uani 1 1 d .
C3 C 0.76176(17) 0.0063(7) 1.0398(3) 0.0480(12) Uani 1 1 d .
C4 C 0.73542(17) -0.0092(7) 0.9498(3) 0.0463(12) Uani 1 1 d .
C5 C 0.68562(18) 0.0108(8) 0.8802(3) 0.0557(14) Uani 1 1 d .
H5 H 0.6669 -0.0040 0.8204 0.067 Uiso 1 1 calc R
C6 C 0.75776(17) -0.0441(7) 0.9296(3) 0.0471(12) Uani 1 1 d .
C7 C 0.73046(19) -0.0245(8) 0.8404(4) 0.0649(16) Uani 1 1 d .
H7 H 0.6976 0.0121 0.7928 0.078 Uiso 1 1 calc R
C8 C 0.7505(2) -0.0572(9) 0.8206(4) 0.0700(17) Uani 1 1 d .
H8 H 0.7312 -0.0427 0.7603 0.084 Uiso 1 1 calc R
C9 C 0.79951(19) -0.1120(8) 0.8902(4) 0.0555(13) Uani 1 1 d .
C10 C 0.82744(18) -0.1289(7) 0.9797(4) 0.0566(14) Uani 1 1 d .
H10 H 0.8605 -0.1624 1.0275 0.068 Uiso 1 1 calc R
C11 C 0.80686(17) -0.0969(8) 0.9985(3) 0.0560(14) Uani 1 1 d .
H11 H 0.8262 -0.1108 1.0589 0.067 Uiso 1 1 calc R
C12 C 0.8209(2) -0.1431(9) 0.8701(4) 0.0646(16) Uani 1 1 d .
C13 C 0.65344(16) 0.1160(7) 0.9723(3) 0.0481(12) Uani 1 1 d .
C14 C 0.67058(18) 0.1266(8) 1.0515(3) 0.0568(14) Uani 1 1 d .
H14 H 0.7034 0.0974 1.1085 0.068 Uiso 1 1 calc R
C15 C 0.64074(18) 0.1786(8) 1.0485(3) 0.0598(15) Uani 1 1 d .
H15 H 0.6534 0.1809 1.1030 0.072 Uiso 1 1 calc R
C16 C 0.59131(18) 0.2283(8) 0.9647(3) 0.0565(14) Uani 1 1 d .
C17 C 0.57417(17) 0.2182(9) 0.8860(3) 0.0640(16) Uani 1 1 d .
H17 H 0.5416 0.2506 0.8292 0.077 Uiso 1 1 calc R
C18 C 0.60402(18) 0.1615(8) 0.8894(4) 0.0624(16) Uani 1 1 d .
H18 H 0.5908 0.1531 0.8345 0.075 Uiso 1 1 calc R
C19 C 0.52204(18) 0.4236(9) 0.8896(3) 0.0571(14) Uani 1 1 d .
C20 C 0.5329(2) 0.5993(10) 0.8847(4) 0.0759(18) Uani 1 1 d .
H20 H 0.5655 0.6311 0.9270 0.091 Uiso 1 1 calc R
C21 C 0.4960(3) 0.7303(10) 0.8177(4) 0.085(2) Uani 1 1 d .
H21 H 0.5037 0.8498 0.8150 0.102 Uiso 1 1 calc R
C22 C 0.4478(3) 0.6816(11) 0.7549(4) 0.085(2) Uani 1 1 d .
H22 H 0.4227 0.7685 0.7094 0.102 Uiso 1 1 calc R
C23 C 0.4367(2) 0.5069(11) 0.7593(4) 0.081(2) Uani 1 1 d .
H23 H 0.4041 0.4746 0.7165 0.097 Uiso 1 1 calc R
C24 C 0.47374(19) 0.3775(9) 0.8270(4) 0.0654(16) Uani 1 1 d .
H24 H 0.4660 0.2590 0.8303 0.079 Uiso 1 1 calc R
C25 C 0.56406(18) 0.2147(9) 1.0191(3) 0.0561(14) Uani 1 1 d .
C26 C 0.5531(2) 0.3335(10) 1.0457(4) 0.0758(18) Uani 1 1 d .
H26 H 0.5449 0.4611 1.0274 0.091 Uiso 1 1 calc R
C27 C 0.5544(2) 0.2596(12) 1.0999(4) 0.092(2) Uani 1 1 d .
H27 H 0.5462 0.3384 1.1166 0.111 Uiso 1 1 calc R
C28 C 0.5673(2) 0.0738(13) 1.1294(4) 0.090(2) Uani 1 1 d .
H28 H 0.5682 0.0266 1.1660 0.108 Uiso 1 1 calc R
C29 C 0.5789(2) -0.0409(11) 1.1043(4) 0.086(2) Uani 1 1 d .
H29 H 0.5886 -0.1666 1.1253 0.103 Uiso 1 1 calc R
C30 C 0.5764(2) 0.0271(9) 1.0476(4) 0.0694(17) Uani 1 1 d .
H30 H 0.5831 -0.0543 1.0288 0.083 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 S1 N2 101.2(3)
C2 N1 S1 106.4(4)
C3 N2 S1 106.4(4)
C1 N3 C5 120.9(4)
C16 N4 C25 122.2(4)
C16 N4 C19 119.0(4)
C25 N4 C19 118.7(4)
N3 C1 C2 116.6(5)
N3 C1 C13 117.9(4)
C2 C1 C13 125.5(4)
N1 C2 C3 113.4(4)
N1 C2 C1 125.4(5)
C3 C2 C1 121.3(5)
N2 C3 C4 127.6(5)
N2 C3 C2 112.6(4)
C4 C3 C2 119.8(5)
C5 C4 C3 113.2(5)
C5 C4 C6 121.3(4)
C3 C4 C6 125.5(4)
N3 C5 C4 128.1(5)
C11 C6 C7 116.8(5)
C11 C6 C4 121.8(4)
C7 C6 C4 121.5(5)
C8 C7 C6 122.1(5)
C7 C8 C9 120.4(5)
C10 C9 C8 118.3(5)
C10 C9 C12 121.2(5)
C8 C9 C12 120.5(5)
C11 C10 C9 120.8(5)
C10 C11 C6 121.7(5)
N5 C12 C9 178.9(7)
C14 C13 C18 116.0(5)
C14 C13 C1 125.6(5)
C18 C13 C1 118.3(4)
C15 C14 C13 122.1(5)
C14 C15 C16 121.1(5)
C17 C16 N4 120.6(5)
C17 C16 C15 117.0(5)
N4 C16 C15 122.4(5)
C18 C17 C16 121.5(5)
C17 C18 C13 122.3(5)
C20 C19 C24 119.4(6)
C20 C19 N4 120.6(5)
C24 C19 N4 120.0(6)
C19 C20 C21 120.8(6)
C22 C21 C20 119.2(7)
C23 C22 C21 120.2(6)
C22 C23 C24 120.4(6)
C19 C24 C23 120.0(6)
C30 C25 C26 119.4(5)
C30 C25 N4 121.9(5)
C26 C25 N4 118.6(5)
C25 C26 C27 119.0(7)
C28 C27 C26 121.6(7)
C29 C28 C27 118.9(7)
C28 C29 C30 120.8(7)
C25 C30 C29 120.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.603(5)
S1 N2 1.614(4)
N1 C2 1.358(6)
N2 C3 1.360(7)
N3 C1 1.329(6)
N3 C5 1.354(6)
N4 C16 1.400(6)
N4 C25 1.425(6)
N4 C19 1.432(7)
N5 C12 1.136(6)
C1 C2 1.441(7)
C1 C13 1.459(6)
C2 C3 1.425(6)
C3 C4 1.425(7)
C4 C5 1.367(7)
C4 C6 1.485(6)
C6 C11 1.390(7)
C6 C7 1.394(7)
C7 C8 1.369(7)
C8 C9 1.390(7)
C9 C10 1.388(7)
C9 C12 1.433(7)
C10 C11 1.371(6)
C13 C14 1.390(6)
C13 C18 1.392(7)
C14 C15 1.369(6)
C15 C16 1.402(8)
C16 C17 1.378(7)
C17 C18 1.370(6)
C19 C20 1.367(8)
C19 C24 1.376(7)
C20 C21 1.384(8)
C21 C22 1.377(9)
C22 C23 1.361(9)
C23 C24 1.381(8)
C25 C30 1.374(7)
C25 C26 1.384(7)
C26 C27 1.385(8)
C27 C28 1.367(9)
C28 C29 1.359(9)
C29 C30 1.387(8)
