#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:03:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178735 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/46/4084692.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_4084692
loop_
_publ_author_name
'Tao, Tao'
'Qian, Hui-Fen'
'Huang, Wei'
'You, Xiao-Zeng'
_publ_section_title
;
 Tuning the Spectroscopic, Electrochemical, and Single-Crystal Conductance
 Properties of a Series of Rhenium-Containing Bithiazoles with Different
 Donor/Acceptor Hybrids
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5120
_journal_paper_doi               10.1021/om500168j
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C50 H42 N4 S2'
_chemical_formula_sum            'C50 H42 N4 S2'
_chemical_formula_weight         763.00
_chemical_name_systematic
; 
 ? 
;
_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                97.960(3)
_cell_angle_beta                 103.410(3)
_cell_angle_gamma                111.124(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3291(14)
_cell_length_b                   10.8951(19)
_cell_length_c                   12.605(2)
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.33
_cell_volume                     1006.3(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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5592
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0455
_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)+(0.0876P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                2838
_reflns_number_total             3511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500168j_si_004.cif
_cod_data_source_block           6
_cod_database_code               4084692
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
C3 C 0.0329(3) -0.4280(2) 0.50058(16) 0.0551(5) Uani 1 1 d .
C2 C 0.0493(3) -0.2405(2) 0.44663(16) 0.0536(5) Uani 1 1 d .
C1 C 0.1863(3) -0.1828(2) 0.54685(15) 0.0520(5) Uani 1 1 d .
C4 C 0.2973(2) -0.0396(2) 0.60659(15) 0.0513(5) Uani 1 1 d .
C5 C 0.3685(3) 0.0597(2) 0.54995(16) 0.0562(5) Uani 1 1 d .
H5 H 0.3451 0.0338 0.4726 0.067 Uiso 1 1 calc R
C6 C 0.4710(3) 0.1931(2) 0.60486(16) 0.0581(5) Uani 1 1 d .
H6 H 0.5178 0.2569 0.5659 0.070 Uiso 1 1 calc R
C7 C 0.5035(2) 0.2308(2) 0.72062(16) 0.0512(5) Uani 1 1 d .
C8 C 0.4370(2) 0.1342(2) 0.78024(15) 0.0488(4) Uani 1 1 d .
C9 C 0.3348(2) -0.0004(2) 0.72269(15) 0.0507(5) Uani 1 1 d .
H9 H 0.2910 -0.0650 0.7618 0.061 Uiso 1 1 calc R
C10 C 0.4951(2) 0.2064(2) 0.89648(15) 0.0509(5) Uani 1 1 d .
C11 C 0.5960(3) 0.3431(2) 0.90280(15) 0.0540(5) Uani 1 1 d .
C12 C 0.6706(3) 0.4411(2) 1.00404(18) 0.0646(6) Uani 1 1 d .
H12 H 0.7386 0.5315 1.0080 0.078 Uiso 1 1 calc R
C13 C 0.6397(3) 0.3991(3) 1.09814(18) 0.0733(6) Uani 1 1 d .
H13 H 0.6883 0.4625 1.1670 0.088 Uiso 1 1 calc R
C14 C 0.5381(3) 0.2646(3) 1.09305(17) 0.0724(6) Uani 1 1 d .
H14 H 0.5188 0.2400 1.1583 0.087 Uiso 1 1 calc R
C15 C 0.4658(3) 0.1675(2) 0.99387(16) 0.0615(5) Uani 1 1 d .
H15 H 0.3986 0.0774 0.9913 0.074 Uiso 1 1 calc R
C16 C 0.6801(3) 0.4814(2) 0.76417(17) 0.0572(5) Uani 1 1 d .
C17 C 0.5758(3) 0.5187(2) 0.6837(2) 0.0688(6) Uani 1 1 d .
H17 H 0.4532 0.4643 0.6507 0.083 Uiso 1 1 calc R
C18 C 0.6553(4) 0.6376(3) 0.6527(2) 0.0878(8) Uani 1 1 d .
H18 H 0.5871 0.6631 0.5977 0.105 Uiso 1 1 calc R
C19 C 0.8378(5) 0.7186(3) 0.7043(3) 0.0953(9) Uani 1 1 d .
H19 H 0.8918 0.7988 0.6839 0.114 Uiso 1 1 calc R
C20 C 0.9373(4) 0.6817(3) 0.7838(3) 0.0924(8) Uani 1 1 d .
H20 H 1.0589 0.7377 0.8186 0.111 Uiso 1 1 calc R
C21 C 0.8615(3) 0.5629(2) 0.8139(2) 0.0737(6) Uani 1 1 d .
H21 H 0.9318 0.5374 0.8676 0.088 Uiso 1 1 calc R
C22 C -0.0121(3) -0.1701(2) 0.36142(18) 0.0647(6) Uani 1 1 d .
H22A H 0.0262 -0.0752 0.3972 0.078 Uiso 1 1 calc R
H22B H -0.1430 -0.2108 0.3325 0.078 Uiso 1 1 calc R
C23 C 0.0685(4) -0.1816(3) 0.2625(2) 0.0799(7) Uani 1 1 d .
H23A H 0.1991 -0.1349 0.2920 0.096 Uiso 1 1 calc R
H23B H 0.0396 -0.2766 0.2326 0.096 Uiso 1 1 calc R
C24 C 0.0044(4) -0.1258(4) 0.1693(2) 0.1005(9) Uani 1 1 d .
H24A H 0.0241 -0.0329 0.1996 0.121 Uiso 1 1 calc R
H24B H -0.1246 -0.1777 0.1350 0.121 Uiso 1 1 calc R
C25 C 0.0950(5) -0.1279(5) 0.0819(3) 0.1343(14) Uani 1 1 d .
H25A H 0.2176 -0.0615 0.1108 0.201 Uiso 1 1 calc R
H25B H 0.0323 -0.1072 0.0174 0.201 Uiso 1 1 calc R
H25C H 0.0939 -0.2163 0.0604 0.201 Uiso 1 1 calc R
N1 N -0.0372(2) -0.37964(17) 0.42180(13) 0.0581(4) Uani 1 1 d .
N2 N 0.6004(2) 0.35746(17) 0.79461(13) 0.0568(4) Uani 1 1 d .
S1 S 0.21014(7) -0.30924(5) 0.60948(4) 0.0588(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 C3 C3 123.9(2) . 2_546
N1 C3 S1 115.08(15) . .
C3 C3 S1 121.06(19) 2_546 .
C1 C2 N1 114.98(18) . .
C1 C2 C22 127.74(19) . .
N1 C2 C22 117.27(17) . .
C2 C1 C4 131.00(19) . .
C2 C1 S1 109.29(15) . .
C4 C1 S1 119.56(14) . .
C9 C4 C5 118.59(19) . .
C9 C4 C1 119.48(17) . .
C5 C4 C1 121.93(18) . .
C6 C5 C4 122.23(18) . .
C6 C5 H5 118.9 . .
C4 C5 H5 118.9 . .
C5 C6 C7 118.33(18) . .
C5 C6 H6 120.8 . .
C7 C6 H6 120.8 . .
N2 C7 C6 129.57(18) . .
N2 C7 C8 109.40(16) . .
C6 C7 C8 121.02(19) . .
C9 C8 C7 119.46(17) . .
C9 C8 C10 133.86(17) . .
C7 C8 C10 106.67(17) . .
C8 C9 C4 120.35(17) . .
C8 C9 H9 119.8 . .
C4 C9 H9 119.8 . .
C15 C10 C11 119.43(18) . .
C15 C10 C8 133.51(19) . .
C11 C10 C8 107.03(16) . .
C12 C11 C10 121.64(18) . .
C12 C11 N2 129.53(19) . .
C10 C11 N2 108.81(17) . .
C13 C12 C11 117.3(2) . .
C13 C12 H12 121.3 . .
C11 C12 H12 121.3 . .
C12 C13 C14 121.7(2) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C15 C14 C13 121.2(2) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
C14 C15 C10 118.7(2) . .
C14 C15 H15 120.7 . .
C10 C15 H15 120.7 . .
C21 C16 C17 120.2(2) . .
C21 C16 N2 120.0(2) . .
C17 C16 N2 119.79(19) . .
C16 C17 C18 119.4(2) . .
C16 C17 H17 120.3 . .
C18 C17 H17 120.3 . .
C17 C18 C19 119.5(3) . .
C17 C18 H18 120.3 . .
C19 C18 H18 120.3 . .
C20 C19 C18 120.5(3) . .
C20 C19 H19 119.8 . .
C18 C19 H19 119.8 . .
C19 C20 C21 120.8(3) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
C20 C21 C16 119.6(3) . .
C20 C21 H21 120.2 . .
C16 C21 H21 120.2 . .
C2 C22 C23 110.62(19) . .
C2 C22 H22A 109.5 . .
C23 C22 H22A 109.5 . .
C2 C22 H22B 109.5 . .
C23 C22 H22B 109.5 . .
H22A C22 H22B 108.1 . .
C24 C23 C22 115.0(2) . .
C24 C23 H23A 108.5 . .
C22 C23 H23A 108.5 . .
C24 C23 H23B 108.5 . .
C22 C23 H23B 108.5 . .
H23A C23 H23B 107.5 . .
C23 C24 C25 113.5(3) . .
C23 C24 H24A 108.9 . .
C25 C24 H24A 108.9 . .
C23 C24 H24B 108.9 . .
C25 C24 H24B 108.9 . .
H24A C24 H24B 107.7 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C3 N1 C2 111.01(16) . .
C7 N2 C11 108.08(15) . .
C7 N2 C16 125.52(16) . .
C11 N2 C16 126.28(17) . .
C3 S1 C1 89.60(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 N1 1.305(3) .
C3 C3 1.459(4) 2_546
C3 S1 1.712(2) .
C2 C1 1.374(3) .
C2 N1 1.375(3) .
C2 C22 1.503(3) .
C1 C4 1.473(3) .
C1 S1 1.728(2) .
C4 C9 1.393(3) .
C4 C5 1.407(3) .
C5 C6 1.369(3) .
C5 H5 0.9300 .
C6 C7 1.394(3) .
C6 H6 0.9300 .
C7 N2 1.384(3) .
C7 C8 1.404(3) .
C8 C9 1.386(3) .
C8 C10 1.441(3) .
C9 H9 0.9300 .
C10 C15 1.398(3) .
C10 C11 1.401(3) .
C11 C12 1.390(3) .
C11 N2 1.401(2) .
C12 C13 1.375(3) .
C12 H12 0.9300 .
C13 C14 1.387(3) .
C13 H13 0.9300 .
C14 C15 1.367(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C21 1.380(3) .
C16 C17 1.382(3) .
C16 N2 1.424(3) .
C17 C18 1.382(3) .
C17 H17 0.9300 .
C18 C19 1.388(4) .
C18 H18 0.9300 .
C19 C20 1.348(4) .
C19 H19 0.9300 .
C20 C21 1.370(4) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 C23 1.558(3) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.475(4) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C25 1.475(5) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
N1 C2 C1 C4 -173.72(19) .
C22 C2 C1 C4 8.0(4) .
N1 C2 C1 S1 1.7(2) .
C22 C2 C1 S1 -176.59(17) .
C2 C1 C4 C9 137.5(2) .
S1 C1 C4 C9 -37.5(2) .
C2 C1 C4 C5 -42.9(3) .
S1 C1 C4 C5 142.07(17) .
C9 C4 C5 C6 -0.8(3) .
C1 C4 C5 C6 179.67(19) .
C4 C5 C6 C7 -0.7(3) .
C5 C6 C7 N2 -179.5(2) .
C5 C6 C7 C8 1.7(3) .
N2 C7 C8 C9 179.82(17) .
C6 C7 C8 C9 -1.2(3) .
N2 C7 C8 C10 0.7(2) .
C6 C7 C8 C10 179.69(18) .
C7 C8 C9 C4 -0.4(3) .
C10 C8 C9 C4 178.52(19) .
C5 C4 C9 C8 1.3(3) .
C1 C4 C9 C8 -179.14(17) .
C9 C8 C10 C15 -1.9(4) .
C7 C8 C10 C15 177.1(2) .
C9 C8 C10 C11 -179.7(2) .
C7 C8 C10 C11 -0.8(2) .
C15 C10 C11 C12 1.0(3) .
C8 C10 C11 C12 179.24(19) .
C15 C10 C11 N2 -177.65(18) .
C8 C10 C11 N2 0.6(2) .
C10 C11 C12 C13 -0.7(3) .
N2 C11 C12 C13 177.6(2) .
C11 C12 C13 C14 -0.2(4) .
C12 C13 C14 C15 0.8(4) .
C13 C14 C15 C10 -0.5(4) .
C11 C10 C15 C14 -0.4(3) .
C8 C10 C15 C14 -178.1(2) .
C21 C16 C17 C18 0.7(4) .
N2 C16 C17 C18 -178.4(2) .
C16 C17 C18 C19 -1.1(4) .
C17 C18 C19 C20 0.2(5) .
C18 C19 C20 C21 1.1(5) .
C19 C20 C21 C16 -1.5(4) .
C17 C16 C21 C20 0.5(4) .
N2 C16 C21 C20 179.7(2) .
C1 C2 C22 C23 99.5(3) .
N1 C2 C22 C23 -78.7(2) .
C2 C22 C23 C24 175.1(2) .
C22 C23 C24 C25 175.1(3) .
C3 C3 N1 C2 178.5(2) 2_546
S1 C3 N1 C2 -0.8(2) .
C1 C2 N1 C3 -0.6(3) .
C22 C2 N1 C3 177.84(18) .
C6 C7 N2 C11 -179.2(2) .
C8 C7 N2 C11 -0.3(2) .
C6 C7 N2 C16 4.5(3) .
C8 C7 N2 C16 -176.57(18) .
C12 C11 N2 C7 -178.7(2) .
C10 C11 N2 C7 -0.2(2) .
C12 C11 N2 C16 -2.5(3) .
C10 C11 N2 C16 176.05(18) .
C21 C16 N2 C7 -125.8(2) .
C17 C16 N2 C7 53.3(3) .
C21 C16 N2 C11 58.6(3) .
C17 C16 N2 C11 -122.2(2) .
N1 C3 S1 C1 1.47(17) .
C3 C3 S1 C1 -177.8(2) 2_546
C2 C1 S1 C3 -1.71(15) .
C4 C1 S1 C3 174.32(16) .
