#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028045.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_4028045
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         'C20 H24 N6 S2'
_chemical_formula_sum            'C20 H24 N6 S2'
_chemical_formula_weight         412.57
_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                 107.022(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.393(2)
_cell_length_b                   8.3690(14)
_cell_length_c                   10.1189(16)
_cell_measurement_reflns_used    6731
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.9
_cell_volume                     1084.5(3)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5135
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0385
_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)+(0.0672P)²+0.0416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1507
_reflns_number_total             1896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302706t_si_003_3.cif
_cod_data_source_block           2Im2TZ
_cod_database_code               4028045
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
C1 C 0.03267(14) 0.9953(2) 0.95373(18) 0.0497(5) Uani 1 1 d .
C2 C 0.15948(14) 0.9170(2) 0.87060(19) 0.0506(5) Uani 1 1 d .
C3 C 0.25160(17) 0.8160(3) 0.8715(2) 0.0663(6) Uani 1 1 d .
H3A H 0.2783 0.8497 0.7966 0.080 Uiso 1 1 calc R
H3B H 0.2291 0.7058 0.8545 0.080 Uiso 1 1 calc R
C4 C 0.33900(18) 0.8249(3) 1.0062(3) 0.0849(8) Uani 1 1 d .
H4A H 0.3638 0.9342 1.0213 0.102 Uiso 1 1 calc R
H4B H 0.3118 0.7954 1.0817 0.102 Uiso 1 1 calc R
C5 C 0.4298(2) 0.7167(5) 1.0077(4) 0.1161(11) Uani 1 1 d U
H5A H 0.4046 0.6078 0.9909 0.139 Uiso 1 1 calc R
H5B H 0.4574 0.7473 0.9328 0.139 Uiso 1 1 calc R
C6 C 0.5141(3) 0.7216(8) 1.1369(5) 0.205(3) Uani 1 1 d U
H6A H 0.5370 0.8299 1.1572 0.308 Uiso 1 1 calc R
H6B H 0.5713 0.6575 1.1284 0.308 Uiso 1 1 calc R
H6C H 0.4895 0.6805 1.2103 0.308 Uiso 1 1 calc R
C7 C 0.11868(14) 1.0374(2) 0.78183(18) 0.0510(5) Uani 1 1 d .
C8 C 0.15735(17) 1.0110(3) 0.5578(2) 0.0670(6) Uani 1 1 d .
H8 H 0.1249 0.9128 0.5328 0.080 Uiso 1 1 calc R
C9 C 0.24288(18) 1.2227(3) 0.5587(2) 0.0701(6) Uani 1 1 d .
H9 H 0.2829 1.3005 0.5325 0.084 Uiso 1 1 calc R
C10 C 0.21109(17) 1.2313(3) 0.6726(2) 0.0639(6) Uani 1 1 d .
H10 H 0.2236 1.3134 0.7373 0.077 Uiso 1 1 calc R
N1 N 0.10849(12) 0.89349(18) 0.96947(16) 0.0528(4) Uani 1 1 d .
N2 N 0.15629(13) 1.09295(19) 0.67298(15) 0.0531(4) Uani 1 1 d .
N3 N 0.20917(16) 1.0861(2) 0.48619(18) 0.0727(5) Uani 1 1 d .
S1 S 0.01391(4) 1.12603(6) 0.81784(5) 0.0569(2) 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'
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 123.4(2) . 3_577
N1 C1 S1 116.23(13) . .
C1 C1 S1 120.33(19) 3_577 .
C7 C2 N1 113.44(16) . .
C7 C2 C3 126.68(17) . .
N1 C2 C3 119.86(16) . .
C2 C3 C4 113.37(18) . .
C2 C3 H3A 108.9 . .
C4 C3 H3A 108.9 . .
C2 C3 H3B 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C5 C4 C3 112.8(2) . .
C5 C4 H4A 109.0 . .
C3 C4 H4A 109.0 . .
C5 C4 H4B 109.0 . .
C3 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C6 C5 C4 113.7(3) . .
C6 C5 H5A 108.8 . .
C4 C5 H5A 108.8 . .
C6 C5 H5B 108.8 . .
C4 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C2 C7 N2 126.42(17) . .
C2 C7 S1 112.12(13) . .
N2 C7 S1 121.43(14) . .
N3 C8 N2 112.1(2) . .
N3 C8 H8 124.0 . .
N2 C8 H8 124.0 . .
C10 C9 N3 111.62(19) . .
C10 C9 H9 124.2 . .
N3 C9 H9 124.2 . .
C9 C10 N2 105.20(19) . .
C9 C10 H10 127.4 . .
N2 C10 H10 127.4 . .
C1 N1 C2 110.62(16) . .
C8 N2 C10 106.49(17) . .
C8 N2 C7 126.71(18) . .
C10 N2 C7 126.28(16) . .
C8 N3 C9 104.61(18) . .
C1 S1 C7 87.57(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.299(2) .
C1 C1 1.459(3) 3_577
C1 S1 1.7172(18) .
C2 C7 1.354(3) .
C2 N1 1.381(2) .
C2 C3 1.493(3) .
C3 C4 1.516(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.513(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.456(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N2 1.417(2) .
C7 S1 1.7180(18) .
C8 N3 1.302(3) .
C8 N2 1.356(2) .
C8 H8 0.9300 .
C9 C10 1.342(3) .
C9 N3 1.362(3) .
C9 H9 0.9300 .
C10 N2 1.371(3) .
C10 H10 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71614425
