#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:45:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178442 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/63/4026348.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_4026348
loop_
_publ_author_name
'Bin Hu'
'Shu-Jun Fu'
'Feng Xu'
'Tao Tao'
'Hao-Yu Zhu'
'Kou-Sen Cao'
'Wei Huang'
'Xiao-Zeng You'
_publ_section_title
;
 Linear Heterocyclic Aromatic Fluorescence Compounds Having Various
 Donor-Acceptor Spacers Prepared by the Combination of Carbon-Carbon Bond
 and Carbon-Nitrogen Bond Cross-Coupling Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4444
_journal_page_last               4456
_journal_paper_doi               10.1021/jo200065d
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C28 H20 N2 S4'
_chemical_formula_sum            'C28 H20 N2 S4'
_chemical_formula_weight         512.70
_chemical_name_systematic
; 
 ? 
;
_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                 120.036(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.211(5)
_cell_length_b                   7.868(3)
_cell_length_c                   16.060(7)
_cell_measurement_reflns_used    1232
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.525
_cell_measurement_theta_min      2.614
_cell_volume                     1226.4(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5998
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0350
_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)+(0.0255P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                1407
_reflns_number_total             2152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200065d_si_002_13.cif
_cod_data_source_block           26
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4026348
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 1.0640(2) -0.0979(3) 0.42569(16) 0.0566(6) Uani 1 1 d .
H1 H 1.0941 -0.1594 0.4822 0.068 Uiso 1 1 calc R
C2 C 0.9238(2) -0.0790(3) 0.36649(16) 0.0526(6) Uani 1 1 d .
H2 H 0.8631 -0.1275 0.3832 0.063 Uiso 1 1 calc R
C3 C 0.8739(2) 0.0129(2) 0.28156(15) 0.0425(5) Uani 1 1 d .
C4 C 0.9727(2) 0.0787(3) 0.26277(16) 0.0523(6) Uani 1 1 d .
H4 H 0.9458 0.1406 0.2068 0.063 Uiso 1 1 calc R
C5 C 1.1103(2) 0.0528(3) 0.32657(17) 0.0567(6) Uani 1 1 d .
H5 H 1.1737 0.0997 0.3119 0.068 Uiso 1 1 calc R
C6 C 0.7273(2) 0.0433(3) 0.21696(15) 0.0441(6) Uani 1 1 d .
C7 C 0.6673(2) 0.1458(3) 0.13804(15) 0.0444(6) Uani 1 1 d .
H7 H 0.7182 0.2060 0.1167 0.053 Uiso 1 1 calc R
C8 C 0.5226(2) 0.1541(2) 0.09124(15) 0.0425(5) Uani 1 1 d U
C9 C 0.4707(2) 0.0538(2) 0.13553(15) 0.0439(5) Uani 1 1 d .
C10 C 0.3294(2) 0.0215(2) 0.11225(15) 0.0447(5) Uani 1 1 d .
C11 C 0.2854(2) -0.0603(3) 0.16643(16) 0.0578(6) Uani 1 1 d .
H11 H 0.3453 -0.1028 0.2274 0.069 Uiso 1 1 calc R
C12 C 0.1423(2) -0.0749(3) 0.12258(16) 0.0548(6) Uani 1 1 d .
H12 H 0.0983 -0.1279 0.1516 0.066 Uiso 1 1 calc R
C13 C 0.07331(19) -0.0040(2) 0.03312(15) 0.0422(5) Uani 1 1 d .
C14 C 0.4403(2) 0.2625(3) 0.00323(15) 0.0568(6) Uani 1 1 d U
H14A H 0.3836 0.1910 -0.0508 0.085 Uiso 1 1 calc R
H14B H 0.5019 0.3266 -0.0099 0.085 Uiso 1 1 calc R
H14C H 0.3830 0.3390 0.0143 0.085 Uiso 1 1 calc R
N1 N 1.15896(19) -0.0354(2) 0.40839(14) 0.0554(5) Uani 1 1 d .
S1 S 0.60200(6) -0.04867(8) 0.23496(4) 0.0560(2) Uani 1 1 d .
S2 S 0.18886(6) 0.08217(7) 0.00381(4) 0.05201(19) 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 C2 125.1(2) . .
N1 C1 H1 117.5 . .
C2 C1 H1 117.5 . .
C1 C2 C3 119.5(2) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C4 C3 C2 115.8(2) . .
C4 C3 C6 121.5(2) . .
C2 C3 C6 122.7(2) . .
C5 C4 C3 120.2(2) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
N1 C5 C4 124.3(2) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
C7 C6 C3 127.9(2) . .
C7 C6 S1 109.84(16) . .
C3 C6 S1 122.23(16) . .
C6 C7 C8 115.1(2) . .
C6 C7 H7 122.4 . .
C8 C7 H7 122.4 . .
C9 C8 C7 111.79(19) . .
C9 C8 C14 126.33(19) . .
C7 C8 C14 121.88(19) . .
C8 C9 C10 131.0(2) . .
C8 C9 S1 111.10(16) . .
C10 C9 S1 117.86(16) . .
C11 C10 C9 128.0(2) . .
C11 C10 S2 109.58(16) . .
C9 C10 S2 122.39(16) . .
C10 C11 C12 114.2(2) . .
C10 C11 H11 122.9 . .
C12 C11 H11 122.9 . .
C13 C12 C11 113.6(2) . .
C13 C12 H12 123.2 . .
C11 C12 H12 123.2 . .
C12 C13 C13 129.1(2) . 3
C12 C13 S2 109.92(16) . .
C13 C13 S2 121.0(2) 3 .
C8 C14 H14A 109.5 . .
C8 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C8 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C1 N1 C5 115.1(2) . .
C6 S1 C9 92.13(11) . .
C13 S2 C10 92.70(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.322(3) .
C1 C2 1.378(3) .
C1 H1 0.9300 .
C2 C3 1.390(3) .
C2 H2 0.9300 .
C3 C4 1.386(3) .
C3 C6 1.459(3) .
C4 C5 1.374(3) .
C4 H4 0.9300 .
C5 N1 1.337(3) .
C5 H5 0.9300 .
C6 C7 1.362(3) .
C6 S1 1.728(2) .
C7 C8 1.406(3) .
C7 H7 0.9300 .
C8 C9 1.371(3) .
C8 C14 1.507(3) .
C9 C10 1.456(3) .
C9 S1 1.736(2) .
C10 C11 1.358(3) .
C10 S2 1.731(2) .
C11 C12 1.397(3) .
C11 H11 0.9300 .
C12 C13 1.364(3) .
C12 H12 0.9300 .
C13 C13 1.445(4) 3
C13 S2 1.723(2) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
