#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/82/4328294.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_4328294
loop_
_publ_author_name
'Qun Zhao'
'Jason L. Freeman'
'Jianwei Wang'
'Yuanli Zhang'
'Tracy P. Hamilton'
'Christopher M. Lawson'
'Gary M. Gray'
_publ_section_title
;
 Syntheses, X-ray Crystal Structures, and Optical, Fluorescence, and
 Nonlinear Optical Characterizations of Diphenylphosphino-Substituted
 Bithiophenes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2016
_journal_page_last               2030
_journal_paper_doi               10.1021/ic201309k
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C20 H15 O P S2'
_chemical_formula_weight         366.41
_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
_audit_update_record
;
2010-03-22 # Formatted by publCIF
;
_cell_angle_alpha                79.99(3)
_cell_angle_beta                 83.97(3)
_cell_angle_gamma                70.75(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2348(12)
_cell_length_b                   8.5970(17)
_cell_length_c                   17.503(4)
_cell_measurement_reflns_used    316
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      14
_cell_volume                     871.1(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3988
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        1.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needles
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1013P)²+0.5460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                2581
_reflns_number_total             3069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic201309k_si_002_3.cif
_cod_data_source_block           zq511a
_cod_original_cell_volume        871.1(3)
_cod_database_code               4328294
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 0.2788(5) 0.4495(4) 0.20816(17) 0.0367(7) Uani 1 1 d .
C2 C 0.0911(6) 0.4252(5) 0.1859(2) 0.0500(9) Uani 1 1 d .
H2 H -0.0484 0.4510 0.2137 0.060 Uiso 1 1 calc R
C3 C 0.1302(6) 0.3575(5) 0.1168(2) 0.0508(9) Uani 1 1 d .
H3 H 0.0190 0.3329 0.0943 0.061 Uiso 1 1 calc R
C4 C 0.3486(5) 0.3305(4) 0.08529(17) 0.0371(7) Uani 1 1 d .
C5 C 0.4491(5) 0.2614(4) 0.01506(18) 0.0392(7) Uani 1 1 d .
C6 C 0.3287(5) 0.2380(4) -0.04790(16) 0.0351(7) Uani 1 1 d .
H6 H 0.1721 0.2664 -0.0509 0.042 Uiso 1 1 calc R
C7 C 0.4998(8) 0.1629(5) -0.1036(2) 0.0634(11) Uani 1 1 d .
H7 H 0.4635 0.1361 -0.1487 0.076 Uiso 1 1 calc R
C8 C 0.7132(7) 0.1340(5) -0.0868(2) 0.0620(11) Uani 1 1 d .
H8 H 0.8382 0.0866 -0.1187 0.074 Uiso 1 1 calc R
C9 C 0.2537(6) 0.4072(4) 0.37645(17) 0.0395(7) Uani 1 1 d .
C10 C 0.4265(8) 0.3065(6) 0.4240(2) 0.0712(12) Uani 1 1 d .
H10 H 0.5762 0.3018 0.4098 0.085 Uiso 1 1 calc R
C11 C 0.3794(10) 0.2147(7) 0.4914(3) 0.0903(16) Uani 1 1 d .
H11 H 0.4968 0.1482 0.5228 0.108 Uiso 1 1 calc R
C12 C 0.1617(9) 0.2197(6) 0.5128(2) 0.0743(13) Uani 1 1 d .
H12 H 0.1303 0.1576 0.5591 0.089 Uiso 1 1 calc R
C13 C -0.0087(8) 0.3144(6) 0.4671(2) 0.0708(12) Uani 1 1 d .
H13 H -0.1572 0.3163 0.4817 0.085 Uiso 1 1 calc R
C14 C 0.0358(7) 0.4096(5) 0.3982(2) 0.0572(9) Uani 1 1 d .
H14 H -0.0828 0.4748 0.3670 0.069 Uiso 1 1 calc R
C15 C 0.1582(5) 0.7388(4) 0.28892(17) 0.0373(7) Uani 1 1 d .
C16 C 0.2559(6) 0.8461(4) 0.3105(2) 0.0508(8) Uani 1 1 d .
H16 H 0.4053 0.8061 0.3256 0.061 Uiso 1 1 calc R
C17 C 0.1327(7) 1.0132(5) 0.3097(3) 0.0637(11) Uani 1 1 d .
H17 H 0.1997 1.0850 0.3242 0.076 Uiso 1 1 calc R
C18 C -0.0891(7) 1.0732(5) 0.2875(2) 0.0592(10) Uani 1 1 d .
H18 H -0.1721 1.1853 0.2866 0.071 Uiso 1 1 calc R
C19 C -0.1861(6) 0.9655(5) 0.2667(2) 0.0547(9) Uani 1 1 d .
H19 H -0.3357 1.0056 0.2518 0.066 Uiso 1 1 calc R
C20 C -0.0660(6) 0.7999(4) 0.2676(2) 0.0458(8) Uani 1 1 d .
H20 H -0.1348 0.7285 0.2540 0.055 Uiso 1 1 calc R
O O 0.5817(4) 0.5100(3) 0.28766(13) 0.0471(6) Uani 1 1 d .
P P 0.33721(13) 0.52561(10) 0.28986(4) 0.0359(3) Uani 1 1 d .
S1 S 0.50347(13) 0.39110(10) 0.14235(4) 0.0408(3) Uani 1 1 d .
S2 S 0.73433(18) 0.19143(15) -0.00230(6) 0.0660(4) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C2 C1 S1 110.8(2)
C2 C1 P 133.8(2)
S1 C1 P 115.38(17)
C1 C2 C3 112.9(3)
C1 C2 H2 123.6
C3 C2 H2 123.6
C4 C3 C2 113.7(3)
C4 C3 H3 123.1
C2 C3 H3 123.1
C3 C4 C5 128.8(3)
C3 C4 S1 109.9(2)
C5 C4 S1 121.3(2)
C4 C5 C6 127.2(3)
C4 C5 S2 121.6(2)
C6 C5 S2 111.3(2)
C7 C6 C5 106.6(3)
C7 C6 H6 126.7
C5 C6 H6 126.7
C8 C7 C6 115.9(3)
C8 C7 H7 122.1
C6 C7 H7 122.1
C7 C8 S2 113.0(3)
C7 C8 H8 123.5
S2 C8 H8 123.5
C14 C9 C10 118.3(3)
C14 C9 P 125.1(3)
C10 C9 P 116.6(3)
C11 C10 C9 120.8(4)
C11 C10 H10 119.6
C9 C10 H10 119.6
C12 C11 C10 120.3(4)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 120.1(4)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.5(4)
C12 C13 H13 119.7
C14 C13 H13 119.7
C9 C14 C13 120.0(4)
C9 C14 H14 120.0
C13 C14 H14 120.0
C16 C15 C20 119.1(3)
C16 C15 P 116.4(3)
C20 C15 P 124.5(2)
C15 C16 C17 120.4(4)
C15 C16 H16 119.8
C17 C16 H16 119.8
C18 C17 C16 120.0(4)
C18 C17 H17 120.0
C16 C17 H17 120.0
C19 C18 C17 119.3(4)
C19 C18 H18 120.3
C17 C18 H18 120.3
C20 C19 C18 121.1(4)
C20 C19 H19 119.5
C18 C19 H19 119.5
C19 C20 C15 120.0(3)
C19 C20 H20 120.0
C15 C20 H20 120.0
O P C1 110.19(14)
O P C15 111.63(14)
C1 P C15 108.71(15)
O P C9 111.70(15)
C1 P C9 107.62(14)
C15 P C9 106.83(14)
C4 S1 C1 92.74(15)
C8 S2 C5 93.20(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.360(4)
C1 S1 1.714(3)
C1 P 1.788(3)
C2 C3 1.396(5)
C2 H2 0.9300
C3 C4 1.375(4)
C3 H3 0.9300
C4 C5 1.450(4)
C4 S1 1.708(3)
C5 C6 1.473(4)
C5 S2 1.691(3)
C6 C7 1.432(5)
C6 H6 0.9300
C7 C8 1.325(6)
C7 H7 0.9300
C8 S2 1.669(4)
C8 H8 0.9300
C9 C14 1.366(5)
C9 C10 1.388(5)
C9 P 1.803(3)
C10 C11 1.362(6)
C10 H10 0.9300
C11 C12 1.358(7)
C11 H11 0.9300
C12 C13 1.347(6)
C12 H12 0.9300
C13 C14 1.391(5)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.380(5)
C15 C20 1.388(4)
C15 P 1.803(3)
C16 C17 1.387(5)
C16 H16 0.9300
C17 C18 1.379(6)
C17 H17 0.9300
C18 C19 1.374(6)
C18 H18 0.9300
C19 C20 1.371(5)
C19 H19 0.9300
C20 H20 0.9300
O P 1.483(2)
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
S1 C1 C2 C3 0.9(4)
P C1 C2 C3 -178.3(3)
C1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 179.5(3)
C2 C3 C4 S1 -0.2(4)
C3 C4 C5 C6 14.6(5)
S1 C4 C5 C6 -165.7(2)
C3 C4 C5 S2 -163.8(3)
S1 C4 C5 S2 15.9(4)
C4 C5 C6 C7 -178.9(3)
S2 C5 C6 C7 -0.3(3)
C5 C6 C7 C8 -0.1(5)
C6 C7 C8 S2 0.5(5)
C14 C9 C10 C11 -1.1(7)
P C9 C10 C11 178.9(4)
C9 C10 C11 C12 0.3(8)
C10 C11 C12 C13 0.6(8)
C11 C12 C13 C14 -0.8(7)
C10 C9 C14 C13 0.9(6)
P C9 C14 C13 -179.0(3)
C12 C13 C14 C9 0.1(7)
C20 C15 C16 C17 -1.0(5)
P C15 C16 C17 178.5(3)
C15 C16 C17 C18 0.2(6)
C16 C17 C18 C19 0.4(6)
C17 C18 C19 C20 -0.1(6)
C18 C19 C20 C15 -0.8(6)
C16 C15 C20 C19 1.3(5)
P C15 C20 C19 -178.2(3)
C2 C1 P O 174.6(3)
S1 C1 P O -4.6(2)
C2 C1 P C15 -62.7(4)
S1 C1 P C15 118.00(18)
C2 C1 P C9 52.6(4)
S1 C1 P C9 -126.64(18)
C16 C15 P O -19.5(3)
C20 C15 P O 159.9(3)
C16 C15 P C1 -141.3(3)
C20 C15 P C1 38.2(3)
C16 C15 P C9 102.8(3)
C20 C15 P C9 -77.7(3)
C14 C9 P O 173.6(3)
C10 C9 P O -6.4(3)
C14 C9 P C1 -65.4(3)
C10 C9 P C1 114.7(3)
C14 C9 P C15 51.2(3)
C10 C9 P C15 -128.7(3)
C3 C4 S1 C1 0.6(3)
C5 C4 S1 C1 -179.1(3)
C2 C1 S1 C4 -0.9(3)
P C1 S1 C4 178.52(18)
C7 C8 S2 C5 -0.6(3)
C4 C5 S2 C8 179.1(3)
C6 C5 S2 C8 0.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661220
