#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/35/7023579.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_7023579
loop_
_publ_author_name
'Freeman, Jason L.'
'Zhao, Qun'
'Zhang, Yuanli'
'Wang, Jianwei'
'Lawson, Christopher M.'
'Gray, Gary M.'
_publ_section_title
;
 Synthesis, linear and nonlinear optical properties of
 phosphonato-substituted bithiophenes derived from 2,2'-biphenol.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14281
_journal_page_last               14297
_journal_paper_doi               10.1039/c3dt51499d
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C32 H20 O6 P2 S2'
_chemical_formula_weight         626.54
_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                 102.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5662(17)
_cell_length_b                   14.881(3)
_cell_length_c                   11.645(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1449.1(5)
_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  0.1227
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3184
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1178P)²+0.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1835
_reflns_number_gt                2003
_reflns_number_total             2543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt51499d.txt
_cod_data_source_block           jlf3752
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1449.0(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7023579
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 0.4254(4) 0.2514(3) 0.9393(3) 0.0547(9) Uani 1 1 d .
C2 C 0.4751(5) 0.1704(4) 0.9017(4) 0.0730(12) Uani 1 1 d .
H2 H 0.4238 0.1468 0.8294 0.088 Uiso 1 1 calc R
C3 C 0.6005(6) 0.1245(4) 0.9711(5) 0.0913(16) Uani 1 1 d .
H3 H 0.6336 0.0695 0.9467 0.110 Uiso 1 1 calc R
C4 C 0.6758(6) 0.1611(5) 1.0767(5) 0.0976(19) Uani 1 1 d .
H4 H 0.7626 0.1315 1.1231 0.117 Uiso 1 1 calc R
C5 C 0.6246(5) 0.2414(4) 1.1152(4) 0.0795(14) Uani 1 1 d .
H5 H 0.6761 0.2643 1.1878 0.095 Uiso 1 1 calc R
C6 C 0.4971(4) 0.2890(3) 1.0472(3) 0.0594(10) Uani 1 1 d .
C7 C 0.4417(5) 0.3761(3) 1.0859(3) 0.0604(10) Uani 1 1 d .
C8 C 0.5497(7) 0.4411(4) 1.1402(4) 0.0872(17) Uani 1 1 d .
H8 H 0.6587 0.4296 1.1512 0.105 Uiso 1 1 calc R
C9 C 0.5003(10) 0.5221(4) 1.1782(4) 0.105(2) Uani 1 1 d .
H9 H 0.5750 0.5639 1.2156 0.126 Uiso 1 1 calc R
C10 C 0.3385(10) 0.5403(3) 1.1601(4) 0.102(2) Uani 1 1 d .
H10 H 0.3047 0.5954 1.1836 0.122 Uiso 1 1 calc R
C11 C 0.2271(7) 0.4782(3) 1.1077(4) 0.0736(12) Uani 1 1 d .
H11 H 0.1183 0.4903 1.0959 0.088 Uiso 1 1 calc R
C12 C 0.2801(5) 0.3981(2) 1.0733(3) 0.0541(9) Uani 1 1 d .
C13 C 0.0629(4) 0.1927(2) 0.9028(3) 0.0426(7) Uani 1 1 d .
C14 C 0.0026(4) 0.1373(2) 0.8103(3) 0.0502(9) Uani 1 1 d .
H14 H -0.0165 0.1554 0.7320 0.060 Uiso 1 1 calc R
C15 C -0.0272(4) 0.0501(2) 0.8464(3) 0.0490(8) Uani 1 1 d .
H15 H -0.0679 0.0041 0.7944 0.059 Uiso 1 1 calc R
C16 C 0.0096(3) 0.0398(2) 0.9657(3) 0.0393(7) Uani 1 1 d .
O1 O 0.3017(3) 0.29800(17) 0.86417(19) 0.0516(7) Uani 1 1 d .
O2 O 0.1653(3) 0.33149(16) 1.02885(19) 0.0485(6) Uani 1 1 d .
O3 O 0.0276(3) 0.36247(16) 0.8109(2) 0.0623(7) Uani 1 1 d .
P P 0.13001(10) 0.30363(6) 0.89431(7) 0.0434(3) Uani 1 1 d .
S S 0.08425(11) 0.13737(5) 1.03466(7) 0.0470(3) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 122.1(4) . .
C2 C1 O1 118.5(3) . .
C6 C1 O1 119.4(4) . .
C3 C2 C1 120.2(4) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C4 C3 C2 118.9(5) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 121.0(5) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C6 121.3(5) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C1 C6 C5 116.6(4) . .
C1 C6 C7 121.2(4) . .
C5 C6 C7 122.2(4) . .
C8 C7 C12 115.5(4) . .
C8 C7 C6 121.3(4) . .
C12 C7 C6 123.1(3) . .
C9 C8 C7 122.1(5) . .
C9 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
C10 C9 C8 119.2(5) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
C11 C10 C9 120.8(5) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C12 C11 C10 118.3(5) . .
C12 C11 H11 120.8 . .
C10 C11 H11 120.8 . .
C11 C12 C7 123.9(4) . .
C11 C12 O2 118.0(4) . .
C7 C12 O2 118.0(3) . .
C14 C13 S 111.4(3) . .
C14 C13 P 126.5(3) . .
S C13 P 121.91(19) . .
C13 C14 C15 112.6(3) . .
C13 C14 H14 123.7 . .
C15 C14 H14 123.7 . .
C16 C15 C14 113.1(3) . .
C16 C15 H15 123.5 . .
C14 C15 H15 123.5 . .
C15 C16 C16 128.4(3) . 3_557
C15 C16 S 111.2(2) . .
C16 C16 S 120.4(3) 3_557 .
C1 O1 P 119.97(19) . .
C12 O2 P 120.91(19) . .
O3 P O2 117.46(15) . .
O3 P O1 109.79(15) . .
O2 P O1 104.19(13) . .
O3 P C13 116.51(15) . .
O2 P C13 100.62(14) . .
O1 P C13 107.05(14) . .
C16 S C13 91.80(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.381(6) .
C1 C6 1.390(5) .
C1 O1 1.402(4) .
C2 C3 1.377(6) .
C2 H2 0.9300 .
C3 C4 1.372(8) .
C3 H3 0.9300 .
C4 C5 1.380(8) .
C4 H4 0.9300 .
C5 C6 1.395(6) .
C5 H5 0.9300 .
C6 C7 1.484(6) .
C7 C8 1.392(6) .
C7 C12 1.398(6) .
C8 C9 1.382(8) .
C8 H8 0.9300 .
C9 C10 1.382(9) .
C9 H9 0.9300 .
C10 C11 1.373(7) .
C10 H10 0.9300 .
C11 C12 1.366(6) .
C11 H11 0.9300 .
C12 O2 1.413(4) .
C13 C14 1.366(5) .
C13 S 1.717(3) .
C13 P 1.757(3) .
C14 C15 1.405(5) .
C14 H14 0.9300 .
C15 C16 1.365(4) .
C15 H15 0.9300 .
C16 C16 1.457(6) 3_557
C16 S 1.715(3) .
O1 P 1.587(3) .
O2 P 1.585(2) .
O3 P 1.452(3) .
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
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.8(6) . .
O1 C1 C2 C3 177.4(4) . .
C1 C2 C3 C4 -0.8(8) . .
C2 C3 C4 C5 1.9(8) . .
C3 C4 C5 C6 -1.4(8) . .
C2 C1 C6 C5 1.3(6) . .
O1 C1 C6 C5 -176.9(3) . .
C2 C1 C6 C7 -179.9(3) . .
O1 C1 C6 C7 1.9(5) . .
C4 C5 C6 C1 -0.2(6) . .
C4 C5 C6 C7 -179.0(4) . .
C1 C6 C7 C8 -137.6(4) . .
C5 C6 C7 C8 41.1(5) . .
C1 C6 C7 C12 43.8(5) . .
C5 C6 C7 C12 -137.5(4) . .
C12 C7 C8 C9 -0.4(5) . .
C6 C7 C8 C9 -179.1(4) . .
C7 C8 C9 C10 -1.3(7) . .
C8 C9 C10 C11 1.7(7) . .
C9 C10 C11 C12 -0.4(7) . .
C10 C11 C12 C7 -1.4(6) . .
C10 C11 C12 O2 174.6(3) . .
C8 C7 C12 C11 1.8(5) . .
C6 C7 C12 C11 -179.5(3) . .
C8 C7 C12 O2 -174.2(3) . .
C6 C7 C12 O2 4.5(5) . .
S C13 C14 C15 0.4(4) . .
P C13 C14 C15 174.7(3) . .
C13 C14 C15 C16 0.3(5) . .
C14 C15 C16 C16 178.1(4) . 3_557
C14 C15 C16 S -0.9(4) . .
C2 C1 O1 P 108.5(3) . .
C6 C1 O1 P -73.2(4) . .
C11 C12 O2 P 111.1(3) . .
C7 C12 O2 P -72.7(3) . .
C12 O2 P O3 -79.1(3) . .
C12 O2 P O1 42.5(3) . .
C12 O2 P C13 153.3(3) . .
C1 O1 P O3 174.2(3) . .
C1 O1 P O2 47.6(3) . .
C1 O1 P C13 -58.4(3) . .
C14 C13 P O3 46.1(4) . .
S C13 P O3 -140.1(2) . .
C14 C13 P O2 174.3(3) . .
S C13 P O2 -11.9(2) . .
C14 C13 P O1 -77.2(3) . .
S C13 P O1 96.6(2) . .
C15 C16 S C13 0.9(3) . .
C16 C16 S C13 -178.2(3) 3_557 .
C14 C13 S C16 -0.7(3) . .
P C13 S C16 -175.4(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102114458
