#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028047.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_4028047
loop_
_publ_author_name
'Tao Tao'
'Yu-Xin Peng'
'Wei Huang'
'Xiao-Zeng You'
_publ_section_title
;
 Coplanar Bithiazole-Centered Heterocyclic Aromatic Fluorescent Compounds
 Having Different Donor/Acceptor Terminal Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2472
_journal_page_last               2481
_journal_paper_doi               10.1021/jo302706t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C22 H24 N2 S4'
_chemical_formula_sum            'C22 H24 N2 S4'
_chemical_formula_weight         444.67
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.87(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.175(13)
_cell_length_b                   25.53(6)
_cell_length_c                   9.45(2)
_cell_measurement_reflns_used    7417
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      18.4
_cell_measurement_theta_min      2.5
_cell_volume                     1104(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (BRUKER 2000)'
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1019
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5870
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.9572
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2119
_refine_ls_wR_factor_ref         0.2475
_reflns_number_gt                866
_reflns_number_total             1932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302706t_si_003_5.cif
_cod_data_source_block           2T2TZ
_cod_original_cell_volume        1104(5)
_cod_database_code               4028047
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'
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
C1 C 1.4263(12) 0.5199(3) 0.0243(7) 0.0683(16) Uani 1 1 d . . .
C2 C 1.1838(16) 0.5893(3) 0.0259(9) 0.097(2) Uani 1 1 d DU . .
C3 C 1.2134(12) 0.5662(2) 0.1623(7) 0.0717(17) Uani 1 1 d . C .
C4 C 1.1190(11) 0.5845(2) 0.2763(7) 0.0727(17) Uani 1 1 d DU . .
C6 C 1.0559(16) 0.5888(3) 0.5096(9) 0.107(3) Uani 1 1 d D . .
H6 H 1.0820 0.5800 0.6110 0.129 Uiso 1 1 calc R A 1
C7 C 0.9067(19) 0.6279(3) 0.4216(10) 0.117(3) Uani 1 1 d D C .
H7 H 0.7910 0.6487 0.4502 0.140 Uiso 1 1 calc R B 1
N1 N 1.3116(13) 0.5617(2) -0.0482(7) 0.0902(17) Uani 1 1 d . C .
S1 S 1.3938(4) 0.50906(7) 0.19281(19) 0.0823(7) Uani 1 1 d . . .
C5 C 1.168(4) 0.5629(7) 0.4220(15) 0.112(10) Uani 0.607(7) 1 d PD C 1
H5 H 1.2730 0.5320 0.4593 0.135 Uiso 0.607(7) 1 calc PR C 1
S2 S 0.9322(16) 0.6389(3) 0.2561(7) 0.132(3) Uani 0.607(7) 1 d PD C 1
C8 C 1.117(2) 0.6454(4) -0.0214(13) 0.085(3) Uani 0.607(7) 1 d PDU C 1
H8A H 1.1191 0.6656 0.0661 0.102 Uiso 0.607(7) 1 calc PR C 1
H8B H 1.2619 0.6600 -0.0482 0.102 Uiso 0.607(7) 1 calc PR C 1
C9 C 0.823(3) 0.6473(5) -0.1626(15) 0.109(4) Uani 0.607(7) 1 d PDU C 1
H9A H 0.6773 0.6389 -0.1286 0.130 Uiso 0.607(7) 1 calc PR C 1
H9B H 0.8115 0.6208 -0.2387 0.130 Uiso 0.607(7) 1 calc PR C 1
C10 C 0.750(5) 0.6992(6) -0.244(3) 0.158(6) Uani 0.607(7) 1 d PDU C 1
H10A H 0.9311 0.7152 -0.2298 0.190 Uiso 0.607(7) 1 calc PR C 1
H10B H 0.6304 0.6933 -0.3580 0.190 Uiso 0.607(7) 1 calc PR C 1
C11 C 0.601(5) 0.7362(8) -0.192(3) 0.192(8) Uani 0.607(7) 1 d PDU C 1
H11A H 0.6380 0.7277 -0.0856 0.288 Uiso 0.607(7) 1 calc PR C 1
H11B H 0.3945 0.7345 -0.2632 0.288 Uiso 0.607(7) 1 calc PR C 1
H11C H 0.6706 0.7709 -0.1940 0.288 Uiso 0.607(7) 1 calc PR C 1
C5' C 0.927(4) 0.6228(8) 0.2790(19) 0.093(10) Uani 0.393(7) 1 d PDU C 2
H5' H 0.8183 0.6439 0.1906 0.111 Uiso 0.393(7) 1 calc PR C 2
S2' S 1.255(2) 0.5538(4) 0.4523(9) 0.106(3) Uani 0.393(7) 1 d PD C 2
C8' C 0.913(3) 0.6199(7) -0.078(3) 0.128(7) Uani 0.393(7) 1 d PDU C 2
H8'1 H 0.8012 0.6025 -0.1802 0.154 Uiso 0.393(7) 1 calc PR C 2
H8'2 H 0.7905 0.6238 -0.0263 0.154 Uiso 0.393(7) 1 calc PR C 2
C9' C 1.018(5) 0.6709(7) -0.100(4) 0.149(7) Uani 0.393(7) 1 d PDU C 2
H9'1 H 1.1113 0.6647 -0.1667 0.178 Uiso 0.393(7) 1 calc PR C 2
H9'2 H 1.1724 0.6811 0.0044 0.178 Uiso 0.393(7) 1 calc PR C 2
C10' C 0.832(6) 0.7183(9) -0.167(4) 0.151(8) Uani 0.393(7) 1 d PDU C 2
H10C H 0.7907 0.7315 -0.0831 0.181 Uiso 0.393(7) 1 calc PR C 2
H10D H 0.9533 0.7443 -0.1816 0.181 Uiso 0.393(7) 1 calc PR C 2
C11' C 0.549(6) 0.7182(11) -0.316(3) 0.160(9) Uani 0.393(7) 1 d PDU C 2
H11D H 0.5797 0.7066 -0.4036 0.240 Uiso 0.393(7) 1 calc PR C 2
H11E H 0.4694 0.7530 -0.3372 0.240 Uiso 0.393(7) 1 calc PR C 2
H11F H 0.4150 0.6950 -0.3038 0.240 Uiso 0.393(7) 1 calc PR C 2
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'
S S 0.1246 0.1234 '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
N1 C1 C1 126.8(7) . 3_865
N1 C1 S1 114.8(5) . .
C1 C1 S1 118.4(6) 3_865 .
C3 C2 N1 113.3(6) . .
C3 C2 C8 127.5(7) . .
N1 C2 C8 116.3(7) . .
C3 C2 C8' 120.2(11) . .
N1 C2 C8' 117.5(12) . .
C8 C2 C8' 44.8(8) . .
C2 C3 C4 129.4(6) . .
C2 C3 S1 110.3(5) . .
C4 C3 S1 120.3(5) . .
C5 C4 C5' 93.5(9) . .
C5 C4 C3 129.6(7) . .
C5' C4 C3 136.4(8) . .
C5 C4 S2 105.8(7) . .
C5' C4 S2 15.1(10) . .
C3 C4 S2 124.5(5) . .
C5 C4 S2' 14.2(7) . .
C5' C4 S2' 106.3(8) . .
C3 C4 S2' 117.2(5) . .
S2 C4 S2' 117.5(5) . .
C7 C6 C5 105.9(9) . .
C7 C6 S2' 119.1(7) . .
C5 C6 S2' 15.0(7) . .
C7 C6 H6 127.0 . .
C5 C6 H6 127.0 . .
S2' C6 H6 113.4 . .
C6 C7 C5' 104.8(9) . .
C6 C7 S2 116.8(7) . .
C5' C7 S2 15.1(9) . .
C6 C7 H7 121.6 . .
C5' C7 H7 132.7 . .
S2 C7 H7 121.6 . .
C1 N1 C2 112.2(6) . .
C3 S1 C1 89.4(3) . .
C6 C5 C4 118.1(11) . .
C6 C5 H5 120.9 . .
C4 C5 H5 120.9 . .
C4 S2 C7 92.8(5) . .
C9 C8 C2 107.3(9) . .
C9 C8 H8A 110.3 . .
C2 C8 H8A 110.3 . .
C9 C8 H8B 110.3 . .
C2 C8 H8B 110.3 . .
H8A C8 H8B 108.5 . .
C8 C9 C10 113.4(14) . .
C8 C9 H9A 108.9 . .
C10 C9 H9A 108.9 . .
C8 C9 H9B 108.9 . .
C10 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C11 C10 C9 116.7(17) . .
C11 C10 H10A 108.1 . .
C9 C10 H10A 108.1 . .
C11 C10 H10B 108.1 . .
C9 C10 H10B 108.1 . .
H10A C10 H10B 107.3 . .
C4 C5' C7 116.9(11) . .
C4 C5' H5' 121.6 . .
C7 C5' H5' 121.6 . .
C6 S2' C4 92.1(6) . .
C9' C8' C2 105.1(13) . .
C9' C8' H8'1 110.7 . .
C2 C8' H8'1 110.7 . .
C9' C8' H8'2 110.7 . .
C2 C8' H8'2 110.7 . .
H8'1 C8' H8'2 108.8 . .
C8' C9' C10' 125(2) . .
C8' C9' H9'1 106.1 . .
C10' C9' H9'1 106.1 . .
C8' C9' H9'2 106.1 . .
C10' C9' H9'2 106.1 . .
H9'1 C9' H9'2 106.3 . .
C11' C10' C9' 124(3) . .
C11' C10' H10C 106.4 . .
C9' C10' H10C 106.4 . .
C11' C10' H10D 106.4 . .
C9' C10' H10D 106.4 . .
H10C C10' H10D 106.4 . .
C10' C11' H11D 109.5 . .
C10' C11' H11E 109.5 . .
H11D C11' H11E 109.5 . .
C10' C11' H11F 109.5 . .
H11D C11' H11F 109.5 . .
H11E C11' H11F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.259(7) .
C1 C1 1.465(12) 3_865
C1 S1 1.701(7) .
C2 C3 1.360(9) .
C2 N1 1.363(8) .
C2 C8 1.493(9) .
C2 C8' 1.500(11) .
C3 C4 1.453(8) .
C3 S1 1.682(7) .
C4 C5 1.392(10) .
C4 C5' 1.404(11) .
C4 S2 1.653(8) .
C4 S2' 1.669(9) .
C6 C7 1.298(6) .
C6 C5 1.381(10) .
C6 S2' 1.634(8) .
C6 H6 0.9300 .
C7 C5' 1.407(11) .
C7 S2 1.655(9) .
C7 H7 0.9300 .
C5 H5 0.9300 .
C8 C9 1.485(10) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.490(10) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.444(10) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C5' H5' 0.9300 .
C8' C9' 1.464(11) .
C8' H8'1 0.9700 .
C8' H8'2 0.9700 .
C9' C10' 1.491(11) .
C9' H9'1 0.9700 .
C9' H9'2 0.9700 .
C10' C11' 1.483(11) .
C10' H10C 0.9700 .
C10' H10D 0.9700 .
C11' H11D 0.9600 .
C11' H11E 0.9600 .
C11' H11F 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71614424
