#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028049.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_4028049
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         'C32 H36 N2 O4 S2'
_chemical_formula_sum            'C32 H36 N2 O4 S2'
_chemical_formula_weight         576.75
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.203(9)
_cell_angle_beta                 105.772(9)
_cell_angle_gamma                100.009(9)
_cell_formula_units_Z            1
_cell_length_a                   8.436(6)
_cell_length_b                   9.551(7)
_cell_length_c                   10.274(7)
_cell_measurement_reflns_used    4782
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.6
_cell_volume                     754.7(9)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3861
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0354
_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)+(0.0352P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                1867
_reflns_number_total             2623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302706t_si_003_7.cif
_cod_data_source_block           2EB2TZ
_cod_database_code               4028049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.8320(3) 1.1595(3) 0.0401(3) 0.1055(9) Uani 1 1 d .
H1A H 0.7466 1.0748 -0.0240 0.158 Uiso 1 1 calc R
H1B H 0.9078 1.1962 -0.0066 0.158 Uiso 1 1 calc R
H1C H 0.7787 1.2351 0.0716 0.158 Uiso 1 1 calc R
C2 C 0.9276(3) 1.1175(3) 0.1606(3) 0.0828(7) Uani 1 1 d .
H2A H 0.9930 1.0501 0.1313 0.099 Uiso 1 1 calc R
H2B H 1.0058 1.2044 0.2305 0.099 Uiso 1 1 calc R
C3 C 0.8567(3) 0.9502(2) 0.2902(2) 0.0553(5) Uani 1 1 d .
C4 C 0.7229(2) 0.88402(19) 0.34239(19) 0.0462(5) Uani 1 1 d .
C5 C 0.5609(2) 0.9074(2) 0.3054(2) 0.0549(5) Uani 1 1 d .
H5 H 0.5342 0.9674 0.2464 0.066 Uiso 1 1 calc R
C6 C 0.4392(2) 0.8429(2) 0.35492(19) 0.0526(5) Uani 1 1 d .
H6 H 0.3312 0.8598 0.3288 0.063 Uiso 1 1 calc R
C7 C 0.4750(2) 0.75266(19) 0.44355(18) 0.0429(5) Uani 1 1 d .
C8 C 0.6382(2) 0.7294(2) 0.47982(19) 0.0504(5) Uani 1 1 d .
H8 H 0.6655 0.6692 0.5386 0.061 Uiso 1 1 calc R
C9 C 0.7591(2) 0.7943(2) 0.4298(2) 0.0526(5) Uani 1 1 d .
H9 H 0.8672 0.7774 0.4553 0.063 Uiso 1 1 calc R
C10 C 0.3440(2) 0.68024(19) 0.49376(18) 0.0421(4) Uani 1 1 d .
C11 C 0.3514(2) 0.66587(19) 0.62492(18) 0.0424(5) Uani 1 1 d .
C12 C 0.4993(2) 0.7279(2) 0.75811(18) 0.0485(5) Uani 1 1 d .
H12A H 0.4633 0.7861 0.8291 0.058 Uiso 1 1 calc R
H12B H 0.5881 0.7935 0.7408 0.058 Uiso 1 1 calc R
C13 C 0.5720(2) 0.6099(2) 0.81441(18) 0.0535(5) Uani 1 1 d .
H13A H 0.4791 0.5328 0.8125 0.064 Uiso 1 1 calc R
H13B H 0.6296 0.5658 0.7527 0.064 Uiso 1 1 calc R
C14 C 0.6946(3) 0.6673(2) 0.9617(2) 0.0693(6) Uani 1 1 d .
H14A H 0.6350 0.7051 1.0246 0.083 Uiso 1 1 calc R
H14B H 0.7834 0.7489 0.9652 0.083 Uiso 1 1 calc R
C15 C 0.7754(3) 0.5512(3) 1.0134(2) 0.0983(9) Uani 1 1 d .
H15A H 0.6882 0.4658 1.0015 0.147 Uiso 1 1 calc R
H15B H 0.8411 0.5904 1.1111 0.147 Uiso 1 1 calc R
H15C H 0.8482 0.5236 0.9602 0.147 Uiso 1 1 calc R
C16 C 0.0849(2) 0.54314(18) 0.51151(18) 0.0428(5) Uani 1 1 d .
N1 N 0.20371(18) 0.58813(15) 0.63410(15) 0.0448(4) Uani 1 1 d .
O1 O 0.80919(17) 1.04669(16) 0.21977(16) 0.0738(4) Uani 1 1 d .
O2 O 0.99186(18) 0.92071(17) 0.30574(17) 0.0804(5) Uani 1 1 d .
S1 S 0.14284(6) 0.59345(5) 0.37715(5) 0.04944(18) 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'
O O 0.0106 0.0060 '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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C1 108.7(2) . .
O1 C2 H2A 110.0 . .
C1 C2 H2A 110.0 . .
O1 C2 H2B 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.3 . .
O2 C3 O1 122.7(2) . .
O2 C3 C4 125.1(2) . .
O1 C3 C4 112.17(18) . .
C9 C4 C5 118.47(18) . .
C9 C4 C3 119.12(18) . .
C5 C4 C3 122.41(19) . .
C6 C5 C4 120.79(19) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 121.04(17) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C6 C7 C8 117.78(18) . .
C6 C7 C10 121.24(16) . .
C8 C7 C10 120.95(17) . .
C9 C8 C7 120.79(19) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C4 121.13(18) . .
C8 C9 H9 119.4 . .
C4 C9 H9 119.4 . .
C11 C10 C7 130.63(16) . .
C11 C10 S1 109.62(14) . .
C7 C10 S1 119.75(14) . .
C10 C11 N1 115.15(15) . .
C10 C11 C12 127.62(17) . .
N1 C11 C12 117.21(17) . .
C11 C12 C13 113.23(15) . .
C11 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
C11 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C14 C13 C12 113.62(16) . .
C14 C13 H13A 108.8 . .
C12 C13 H13A 108.8 . .
C14 C13 H13B 108.8 . .
C12 C13 H13B 108.8 . .
H13A C13 H13B 107.7 . .
C13 C14 C15 113.24(19) . .
C13 C14 H14A 108.9 . .
C15 C14 H14A 108.9 . .
C13 C14 H14B 108.9 . .
C15 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N1 C16 C16 123.2(2) . 2_566
N1 C16 S1 115.25(14) . .
C16 C16 S1 121.52(18) 2_566 .
C16 N1 C11 110.76(16) . .
C3 O1 C2 117.80(17) . .
C16 S1 C10 89.21(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.457(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 O1 1.447(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 O2 1.198(2) .
C3 O1 1.337(2) .
C3 C4 1.478(3) .
C4 C9 1.379(3) .
C4 C5 1.386(3) .
C5 C6 1.375(3) .
C5 H5 0.9300 .
C6 C7 1.391(2) .
C6 H6 0.9300 .
C7 C8 1.395(2) .
C7 C10 1.470(2) .
C8 C9 1.374(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C11 1.369(3) .
C10 S1 1.7288(19) .
C11 N1 1.373(2) .
C11 C12 1.501(2) .
C12 C13 1.518(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.504(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.514(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 N1 1.308(2) .
C16 C16 1.453(3) 2_566
C16 S1 1.715(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71614619
