#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:56:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178541 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/47/4064775.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_4064775
loop_
_publ_author_name
'Peay, Miya A.'
'Heckler, James E.'
'Deligonul, Nihal'
'Gray, Thomas G.'
_publ_section_title
;
 Red-Shifts upon Metal Binding: A Di-Gold(I)-Substituted Bithiophene
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5071
_journal_paper_doi               10.1021/om2003267
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C44 H34 Au2 P2 S2'
_chemical_formula_sum            'C44 H34 Au2 P2 S2'
_chemical_formula_weight         1082.70
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.362(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.453(3)
_cell_length_b                   13.060(3)
_cell_length_c                   16.282(3)
_cell_measurement_reflns_used    5768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.34
_cell_volume                     3695.0(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker ASX APEX II 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  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20969
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.164
_exptl_absorpt_correction_T_max  0.6445
_exptl_absorpt_correction_T_min  0.2245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'AXScale in APEX 2 (Bruker, 2004)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.406
_refine_diff_density_min         -1.843
_refine_diff_density_rms         0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0376
_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)+(0.1000P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                3088
_reflns_number_total             4214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2003267_si_002.cif
_cod_data_source_block           nd043009_0m
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

 Adding full bibliography for 4064775.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3695.0(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4064775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Au1 Au 0.162083(17) 0.70875(2) 0.143158(18) 0.01882(13) Uani 1 1 d .
S1 S 0.03558(12) 0.88345(16) 0.09291(13) 0.0225(4) Uani 1 1 d .
P1 P 0.22596(12) 0.60089(16) 0.23574(13) 0.0188(4) Uani 1 1 d .
C16 C 0.3342(5) 0.4449(6) 0.2230(5) 0.0251(19) Uani 1 1 d .
H16 H 0.3605 0.4709 0.2723 0.030 Uiso 1 1 calc R
C11 C 0.2670(5) 0.4918(6) 0.1893(5) 0.0239(19) Uani 1 1 d .
C12 C 0.2295(5) 0.4541(6) 0.1165(5) 0.0244(18) Uani 1 1 d .
H12 H 0.1838 0.4862 0.0928 0.029 Uiso 1 1 calc R
C15 C 0.3625(5) 0.3606(7) 0.1849(5) 0.0264(19) Uani 1 1 d .
H15 H 0.4079 0.3279 0.2087 0.032 Uiso 1 1 calc R
C14 C 0.3255(6) 0.3230(7) 0.1124(6) 0.030(2) Uani 1 1 d .
H14 H 0.3459 0.2655 0.0861 0.036 Uiso 1 1 calc R
C13 C 0.2591(5) 0.3688(7) 0.0782(5) 0.0281(19) Uani 1 1 d .
H13 H 0.2333 0.3426 0.0286 0.034 Uiso 1 1 calc R
C4 C 0.0296(5) 0.9612(6) 0.0061(5) 0.0200(17) Uani 1 1 d .
C2 C 0.1322(5) 0.8513(6) -0.0093(5) 0.0225(18) Uani 1 1 d .
H2 H 0.1738 0.8248 -0.0365 0.027 Uiso 1 1 calc R
C1 C 0.1130(5) 0.8142(6) 0.0638(5) 0.0246(19) Uani 1 1 d .
C3 C 0.0851(5) 0.9330(6) -0.0420(5) 0.0246(18) Uani 1 1 d .
H3 H 0.0920 0.9650 -0.0932 0.030 Uiso 1 1 calc R
C10 C 0.3362(5) 0.6441(7) 0.3698(5) 0.0239(18) Uani 1 1 d .
H10 H 0.3131 0.5926 0.4005 0.029 Uiso 1 1 calc R
C5 C 0.3065(5) 0.6663(7) 0.2906(5) 0.0230(18) Uani 1 1 d .
C17 C 0.1698(5) 0.5466(6) 0.3128(5) 0.0209(17) Uani 1 1 d .
C18 C 0.0959(5) 0.5843(7) 0.3201(6) 0.0261(19) Uani 1 1 d .
H18 H 0.0758 0.6368 0.2839 0.031 Uiso 1 1 calc R
C6 C 0.3417(5) 0.7436(7) 0.2469(5) 0.0272(19) Uani 1 1 d .
H6 H 0.3213 0.7605 0.1925 0.033 Uiso 1 1 calc R
C9 C 0.4002(6) 0.6972(7) 0.4049(6) 0.031(2) Uani 1 1 d .
H9 H 0.4202 0.6824 0.4599 0.038 Uiso 1 1 calc R
C8 C 0.4348(6) 0.7711(8) 0.3606(7) 0.039(2) Uani 1 1 d .
H8 H 0.4793 0.8058 0.3842 0.047 Uiso 1 1 calc R
C22 C 0.1975(5) 0.4680(6) 0.3646(5) 0.0227(18) Uani 1 1 d .
H22 H 0.2472 0.4403 0.3596 0.027 Uiso 1 1 calc R
C21 C 0.1525(5) 0.4291(7) 0.4246(5) 0.0270(19) Uani 1 1 d .
H21 H 0.1717 0.3760 0.4606 0.032 Uiso 1 1 calc R
C19 C 0.0519(5) 0.5466(7) 0.3792(6) 0.032(2) Uani 1 1 d .
H19 H 0.0022 0.5740 0.3845 0.039 Uiso 1 1 calc R
C20 C 0.0801(6) 0.4691(7) 0.4306(6) 0.032(2) Uani 1 1 d .
H20 H 0.0493 0.4426 0.4707 0.038 Uiso 1 1 calc R
C7 C 0.4043(6) 0.7943(7) 0.2818(6) 0.035(2) Uani 1 1 d .
H7 H 0.4273 0.8463 0.2515 0.042 Uiso 1 1 calc R
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'
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'
Au Au -2.0133 8.8022 '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
C1 Au1 P1 174.7(3) . .
C1 S1 C4 94.1(4) . .
C11 P1 C17 104.2(4) . .
C11 P1 C5 105.1(4) . .
C17 P1 C5 106.8(4) . .
C11 P1 Au1 113.7(3) . .
C17 P1 Au1 116.0(3) . .
C5 P1 Au1 110.2(3) . .
C15 C16 C11 119.9(9) . .
C15 C16 H16 120.0 . .
C11 C16 H16 120.0 . .
C12 C11 C16 119.6(8) . .
C12 C11 P1 117.8(7) . .
C16 C11 P1 122.6(7) . .
C11 C12 C13 119.9(8) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C16 C15 C14 120.7(9) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C13 C14 C15 120.0(9) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C13 C12 119.9(9) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C3 C4 C4 130.6(9) . 5_575
C3 C4 S1 108.7(6) . .
C4 C4 S1 120.7(8) 5_575 .
C1 C2 C3 114.6(7) . .
C1 C2 H2 122.7 . .
C3 C2 H2 122.7 . .
C2 C1 S1 108.5(6) . .
C2 C1 Au1 132.8(7) . .
S1 C1 Au1 118.4(5) . .
C4 C3 C2 114.1(7) . .
C4 C3 H3 122.9 . .
C2 C3 H3 122.9 . .
C5 C10 C9 119.8(8) . .
C5 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C5 C6 118.7(8) . .
C10 C5 P1 124.8(7) . .
C6 C5 P1 116.4(7) . .
C22 C17 C18 118.8(8) . .
C22 C17 P1 122.1(6) . .
C18 C17 P1 119.1(7) . .
C19 C18 C17 120.9(8) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C7 C6 C5 120.7(9) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C8 C9 C10 120.6(10) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C7 C8 C9 119.5(10) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
C17 C22 C21 120.3(8) . .
C17 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C20 C21 C22 119.3(8) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C20 C19 C18 119.8(9) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C19 C20 C21 120.9(8) . .
C19 C20 H20 119.5 . .
C21 C20 H20 119.5 . .
C6 C7 C8 120.7(9) . .
C6 C7 H7 119.7 . .
C8 C7 H7 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 2.023(9) .
Au1 P1 2.277(2) .
S1 C1 1.729(9) .
S1 C4 1.735(8) .
P1 C11 1.794(9) .
P1 C17 1.808(8) .
P1 C5 1.808(9) .
C16 C15 1.378(12) .
C16 C11 1.390(12) .
C16 H16 0.9500 .
C11 C12 1.389(12) .
C12 C13 1.399(12) .
C12 H12 0.9500 .
C15 C14 1.381(12) .
C15 H15 0.9500 .
C14 C13 1.376(13) .
C14 H14 0.9500 .
C13 H13 0.9500 .
C4 C3 1.354(12) .
C4 C4 1.447(15) 5_575
C2 C1 1.356(11) .
C2 C3 1.418(11) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C10 C5 1.376(11) .
C10 C9 1.391(13) .
C10 H10 0.9500 .
C5 C6 1.408(12) .
C17 C22 1.387(12) .
C17 C18 1.395(12) .
C18 C19 1.378(12) .
C18 H18 0.9500 .
C6 C7 1.355(13) .
C6 H6 0.9500 .
C9 C8 1.377(15) .
C9 H9 0.9500 .
C8 C7 1.376(15) .
C8 H8 0.9500 .
C22 C21 1.404(11) .
C22 H22 0.9500 .
C21 C20 1.379(13) .
C21 H21 0.9500 .
C19 C20 1.374(13) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C7 H7 0.9500 .
