#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:18:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180499 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/68/7216889.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_7216889
_publ_contact_author             'Professor J. S. Field'
_publ_section_title
;
 Novel diphenylphosphine derivatives of 2,2′-bithiophene,
 2,2′:5′,2″-terthiophene,
 2-(2′-thienyl)pyridine and 2,6-di-2′-thienylpyridine.
 Crystal structures of
 5,5′-bis(diphenylphosphino)-2,2′-bithiophene,
 diphenyl{5-[6′-(diphenylphosphino)-2′-pyridyl]-2-thienyl}phosphine
 and 2,6-bis[5′-(diphenylphosphino)-2′-thienyl]pyridine
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3352
_journal_paper_doi               10.1039/b107389n
_journal_year                    2001
_chemical_formula_moiety         '[{P(C6H5)2}2(C4H2S)(C5H3N)]'
_chemical_formula_sum            'C33 H25 N P2 S'
_chemical_formula_weight         529.54
_chemical_melting_point          432.15
_chemical_name_systematic
;
Diphenyl[5-(2'-{6'-diphenylphosphino}pyridyl)-2-thienyl]phosphine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.11(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.408(5)
_cell_length_b                   15.978(6)
_cell_length_c                   20.402(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      2
_cell_volume                     2689(2)
_computing_cell_refinement       'CELDIM, CAD4'
_computing_data_collection       'Nonius CAD4'
_computing_data_reduction        'XCAD (McArdle, 2000)'
_computing_molecular_graphics    'ORTEP 3  (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       'omega-2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       1
_diffrn_reflns_number            3925
_diffrn_reflns_theta_full        22.98
_diffrn_reflns_theta_max         22.98
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0%
_diffrn_standards_interval_time  '60 minutes'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0517
_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)+(0.0000P)²+4.3953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                2173
_reflns_number_total             3616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b107389n.txt
_cod_data_source_block           el08
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '159 C' was changed to '432.15' - it
was converted from degrees Celsius(C) to
Kelvins(K).

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2690(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7216889
#BEGIN Tags that were not found in dictionaries:
_exptl-crystal_preparation
;
Crystals grown from petroleum ether/ether by slow evaporation
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
P1 P -0.39497(19) 1.36499(10) 0.06385(8) 0.0534(4) Uani 1 1 d
P2 P 0.17519(18) 0.95797(10) 0.20249(8) 0.0536(4) Uani 1 1 d
S S -0.23718(17) 1.19705(10) 0.12305(7) 0.0550(4) Uani 1 1 d
N N -0.1134(5) 1.0386(3) 0.18400(19) 0.0454(11) Uani 1 1 d
C1 C -0.3938(7) 1.2676(3) 0.1090(2) 0.0484(14) Uani 1 1 d
C2 C -0.5197(8) 1.2380(4) 0.1347(3) 0.0599(17) Uani 1 1 d
C3 C -0.4907(7) 1.1596(4) 0.1655(3) 0.0556(16) Uani 1 1 d
C4 C -0.3423(6) 1.1283(3) 0.1637(2) 0.0462(14) Uani 1 1 d
C5 C -0.2685(6) 1.0495(3) 0.1897(2) 0.0435(13) Uani 1 1 d
C6 C -0.3516(8) 0.9899(4) 0.2196(3) 0.0575(16) Uani 1 1 d
C7 C -0.2745(8) 0.9171(4) 0.2439(3) 0.0603(17) Uani 1 1 d
C8 C -0.1178(8) 0.9055(4) 0.2360(3) 0.0578(17) Uani 1 1 d
C9 C -0.0409(6) 0.9666(3) 0.2056(2) 0.0464(14) Uani 1 1 d
C10 C -0.1835(7) 1.3788(3) 0.0585(3) 0.0509(15) Uani 1 1 d
C11 C -0.0999(8) 1.3280(5) 0.0210(3) 0.0667(18) Uani 1 1 d
C12 C 0.0609(9) 1.3426(5) 0.0200(4) 0.075(2) Uani 1 1 d
C13 C 0.1382(10) 1.4092(5) 0.0556(4) 0.083(2) Uani 1 1 d
C14 C 0.0617(10) 1.4601(5) 0.0925(4) 0.083(2) Uani 1 1 d
C15 C -0.1004(8) 1.4450(4) 0.0930(3) 0.0670(18) Uani 1 1 d
C16 C -0.4856(6) 1.3342(4) -0.0218(3) 0.0520(15) Uani 1 1 d
C17 C -0.5040(9) 1.3955(5) -0.0700(3) 0.0693(19) Uani 1 1 d
C18 C -0.5812(9) 1.3824(6) -0.1343(4) 0.082(2) Uani 1 1 d
C19 C -0.6426(9) 1.3048(7) -0.1519(4) 0.086(2) Uani 1 1 d
C20 C -0.6260(11) 1.2414(6) -0.1061(4) 0.093(3) Uani 1 1 d
C21 C -0.5485(9) 1.2563(5) -0.0412(4) 0.072(2) Uani 1 1 d
C22 C 0.2013(7) 0.8449(4) 0.2026(3) 0.0512(15) Uani 1 1 d
C23 C 0.3134(7) 0.8086(5) 0.2526(3) 0.0642(18) Uani 1 1 d
C24 C 0.3356(9) 0.7220(6) 0.2540(4) 0.082(2) Uani 1 1 d
C25 C 0.2419(11) 0.6727(5) 0.2072(4) 0.086(2) Uani 1 1 d
C26 C 0.1297(12) 0.7070(5) 0.1594(4) 0.081(2) Uani 1 1 d
C27 C 0.1089(9) 0.7925(4) 0.1569(3) 0.073(2) Uani 1 1 d
C28 C 0.1895(6) 0.9865(4) 0.1169(3) 0.0491(14) Uani 1 1 d
C29 C 0.2832(8) 0.9408(4) 0.0819(4) 0.0650(18) Uani 1 1 d
C30 C 0.3088(10) 0.9665(5) 0.0207(4) 0.081(2) Uani 1 1 d
C31 C 0.2434(9) 1.0400(5) -0.0063(4) 0.078(2) Uani 1 1 d
C32 C 0.1506(9) 1.0875(5) 0.0272(4) 0.0735(19) Uani 1 1 d
C33 C 0.1252(8) 1.0613(4) 0.0890(3) 0.0612(17) Uani 1 1 d
H1 H -0.619(7) 1.266(4) 0.130(3) 0.08(2) Uiso 1 1 d
H2 H -0.567(7) 1.130(4) 0.188(3) 0.074(19) Uiso 1 1 d
H3 H -0.464(7) 1.004(3) 0.219(3) 0.07(2) Uiso 1 1 d
H4 H -0.344(8) 0.869(5) 0.262(3) 0.13(3) Uiso 1 1 d
H5 H -0.071(6) 0.861(3) 0.251(2) 0.039(15) Uiso 1 1 d
H6 H -0.149(6) 1.279(3) 0.005(2) 0.040(15) Uiso 1 1 d
H7 H 0.117(8) 1.293(5) -0.007(3) 0.13(3) Uiso 1 1 d
H8 H 0.250(10) 1.422(5) 0.053(4) 0.13(3) Uiso 1 1 d
H9 H 0.107(9) 1.508(5) 0.119(3) 0.12(3) Uiso 1 1 d
H10 H -0.155(5) 1.481(3) 0.116(2) 0.026(13) Uiso 1 1 d
H11 H -0.470(6) 1.446(3) -0.056(2) 0.044(16) Uiso 1 1 d
H12 H -0.605(10) 1.425(5) -0.166(4) 0.14(3) Uiso 1 1 d
H13 H -0.704(6) 1.289(3) -0.192(3) 0.055(16) Uiso 1 1 d
H14 H -0.656(9) 1.186(5) -0.118(3) 0.11(3) Uiso 1 1 d
H15 H -0.533(7) 1.217(4) -0.010(3) 0.08(2) Uiso 1 1 d
H16 H 0.379(7) 0.845(3) 0.282(3) 0.065(19) Uiso 1 1 d
H17 H 0.413(8) 0.702(4) 0.285(3) 0.10(3) Uiso 1 1 d
H18 H 0.265(7) 0.608(4) 0.211(3) 0.08(2) Uiso 1 1 d
H19 H 0.062(9) 0.678(5) 0.130(3) 0.11(3) Uiso 1 1 d
H20 H 0.026(6) 0.819(3) 0.126(3) 0.060(17) Uiso 1 1 d
H21 H 0.335(6) 0.890(4) 0.099(3) 0.064(18) Uiso 1 1 d
H22 H 0.378(8) 0.933(4) 0.002(3) 0.10(3) Uiso 1 1 d
H23 H 0.256(7) 1.056(4) -0.048(3) 0.08(2) Uiso 1 1 d
H24 H 0.104(6) 1.148(4) 0.013(2) 0.063(17) Uiso 1 1 d
H25 H 0.065(8) 1.093(4) 0.111(3) 0.09(2) Uiso 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'
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
C1 P1 C10 103.1(3)
C1 P1 C16 102.4(3)
C10 P1 C16 102.0(3)
C22 P2 C28 102.6(3)
C22 P2 C9 101.2(3)
C28 P2 C9 105.2(2)
C1 S C4 93.0(3)
C9 N C5 118.1(5)
C2 C1 S 109.7(5)
C2 C1 P1 124.8(4)
S C1 P1 125.5(3)
C1 C2 C3 113.9(6)
C4 C3 C2 113.6(6)
C3 C4 C5 129.8(5)
C3 C4 S 109.8(5)
C5 C4 S 120.3(4)
N C5 C6 122.0(5)
N C5 C4 115.6(5)
C6 C5 C4 122.4(5)
C7 C6 C5 119.6(6)
C8 C7 C6 117.9(6)
C7 C8 C9 120.1(6)
N C9 C8 122.2(5)
N C9 P2 116.5(4)
C8 C9 P2 120.9(5)
C15 C10 C11 117.7(6)
C15 C10 P1 117.9(5)
C11 C10 P1 124.4(5)
C12 C11 C10 120.7(7)
C11 C12 C13 119.1(8)
C14 C13 C12 122.1(8)
C13 C14 C15 118.2(8)
C10 C15 C14 122.1(7)
C17 C16 C21 117.0(6)
C17 C16 P1 117.3(5)
C21 C16 P1 125.5(5)
C18 C17 C16 123.0(7)
C19 C18 C17 118.7(8)
C18 C19 C20 120.6(7)
C19 C20 C21 119.7(8)
C20 C21 C16 121.0(7)
C27 C22 C23 117.6(6)
C27 C22 P2 123.4(5)
C23 C22 P2 118.9(5)
C22 C23 C24 120.1(7)
C25 C24 C23 120.1(7)
C26 C25 C24 120.3(8)
C25 C26 C27 120.1(8)
C22 C27 C26 121.8(7)
C29 C28 C33 117.6(6)
C29 C28 P2 120.9(5)
C33 C28 P2 120.9(5)
C30 C29 C28 121.4(7)
C31 C30 C29 120.2(8)
C32 C31 C30 120.2(7)
C31 C32 C33 119.4(7)
C32 C33 C28 121.2(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.807(6)
P1 C10 1.815(6)
P1 C16 1.834(6)
P2 C22 1.820(6)
P2 C28 1.832(5)
P2 C9 1.835(5)
S C1 1.715(5)
S C4 1.720(5)
N C9 1.336(6)
N C5 1.343(6)
C1 C2 1.355(8)
C2 C3 1.401(8)
C3 C4 1.352(7)
C4 C5 1.458(7)
C5 C6 1.389(7)
C6 C7 1.378(8)
C7 C8 1.370(8)
C8 C9 1.382(8)
C10 C15 1.382(8)
C10 C11 1.395(8)
C11 C12 1.376(9)
C12 C13 1.379(10)
C13 C14 1.352(10)
C14 C15 1.386(9)
C16 C17 1.375(8)
C16 C21 1.380(8)
C17 C18 1.363(9)
C18 C19 1.363(11)
C19 C20 1.369(11)
C20 C21 1.379(9)
C22 C27 1.376(8)
C22 C23 1.377(8)
C23 C24 1.395(10)
C24 C25 1.365(11)
C25 C26 1.337(10)
C26 C27 1.378(9)
C28 C29 1.372(8)
C28 C33 1.387(8)
C29 C30 1.370(9)
C30 C31 1.366(10)
C31 C32 1.362(9)
C32 C33 1.385(8)
