#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/16/4071670.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_4071670
loop_
_publ_author_name
'Kling, Christian'
'Ott, Holger'
'Schwab, Gerald'
'Stalke, Dietmar'
_publ_contact_author             'Prof. Dr. Dietmar Stalke'
_publ_section_title
;
 Heteroaromatic Substituted Phosphoranes with Enhanced Hemilabile
 Character
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5038
_journal_paper_doi               10.1021/om800307d
_journal_volume                  27
_journal_year                    2008
_chemical_formula_sum            'C18 H16 N P S'
_chemical_formula_weight         309.35
_chemical_name_common            S=P(Pic)Ph2
_chemical_name_systematic        'Diphenyl-(2-picolyl)phosphane sulfide'
_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                 99.485(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4129(7)
_cell_length_b                   7.3039(5)
_cell_length_c                   17.1658(11)
_cell_measurement_reflns_used    14316
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      3.31
_cell_volume                     1535.02(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_molecular_graphics    'SHELXTL-NT V6.14'
_computing_publication_material  'SHELXTL-NT V6.14'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS II'
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16794
_diffrn_reflns_theta_full        24.83
_diffrn_reflns_theta_max         24.83
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0268
_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)+(0.0363P)²+0.2289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                2642
_reflns_number_total             2642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800307d_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4071670
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
_atom_site_refinement_flags
C1 C -0.12257(13) 0.2468(2) 0.35074(9) 0.0230(3) Uani 1 1 d .
C2 C -0.18077(14) 0.2470(2) 0.27397(10) 0.0283(4) Uani 1 1 d .
H2A H -0.1442 0.2198 0.2309 0.034 Uiso 1 1 calc R
C3 C -0.29109(14) 0.2864(2) 0.25987(11) 0.0339(4) Uani 1 1 d .
H3A H -0.3302 0.2855 0.2074 0.041 Uiso 1 1 calc R
C4 C -0.34459(14) 0.3274(2) 0.32265(11) 0.0348(4) Uani 1 1 d .
H4A H -0.4203 0.3560 0.3131 0.042 Uiso 1 1 calc R
C5 C -0.28809(14) 0.3265(2) 0.39886(11) 0.0345(4) Uani 1 1 d .
H5A H -0.3251 0.3546 0.4416 0.041 Uiso 1 1 calc R
C6 C -0.17761(14) 0.2850(2) 0.41346(10) 0.0291(4) Uani 1 1 d .
H6A H -0.1394 0.2826 0.4662 0.035 Uiso 1 1 calc R
C7 C 0.07221(12) 0.2773(2) 0.28262(9) 0.0220(3) Uani 1 1 d .
C8 C 0.05882(13) 0.4636(2) 0.26571(9) 0.0262(4) Uani 1 1 d .
H8A H 0.0200 0.5386 0.2968 0.031 Uiso 1 1 calc R
C9 C 0.10202(14) 0.5392(2) 0.20370(10) 0.0287(4) Uani 1 1 d .
H9A H 0.0927 0.6659 0.1921 0.034 Uiso 1 1 calc R
C10 C 0.15899(13) 0.4296(2) 0.15833(9) 0.0277(4) Uani 1 1 d .
H10A H 0.1886 0.4817 0.1158 0.033 Uiso 1 1 calc R
C11 C 0.17280(13) 0.2455(2) 0.17482(9) 0.0274(4) Uani 1 1 d .
H11A H 0.2124 0.1713 0.1439 0.033 Uiso 1 1 calc R
C12 C 0.12888(13) 0.1684(2) 0.23666(9) 0.0245(3) Uani 1 1 d .
H12A H 0.1376 0.0412 0.2475 0.029 Uiso 1 1 calc R
C13 C 0.08282(13) 0.3165(2) 0.45187(9) 0.0251(3) Uani 1 1 d .
H13A H 0.0702 0.4480 0.4397 0.030 Uiso 1 1 calc R
H13B H 0.0463 0.2864 0.4974 0.030 Uiso 1 1 calc R
C14 C 0.20332(13) 0.2842(2) 0.47487(9) 0.0233(3) Uani 1 1 d .
C15 C 0.24368(14) 0.1641(2) 0.53544(10) 0.0297(4) Uani 1 1 d .
H15A H 0.1951 0.0988 0.5627 0.036 Uiso 1 1 calc R
C16 C 0.35508(15) 0.1406(2) 0.55563(10) 0.0347(4) Uani 1 1 d .
H16A H 0.3844 0.0598 0.5971 0.042 Uiso 1 1 calc R
C17 C 0.42322(14) 0.2368(2) 0.51428(10) 0.0333(4) Uani 1 1 d .
H17A H 0.5003 0.2233 0.5265 0.040 Uiso 1 1 calc R
C18 C 0.37649(14) 0.3531(2) 0.45473(10) 0.0300(4) Uani 1 1 d .
H18A H 0.4237 0.4186 0.4264 0.036 Uiso 1 1 calc R
N1 N 0.26895(11) 0.37909(18) 0.43458(8) 0.0261(3) Uani 1 1 d .
P1 P 0.02021(3) 0.18128(5) 0.36638(2) 0.02101(11) Uani 1 1 d .
S1 S 0.04611(3) -0.08248(5) 0.38004(2) 0.02523(11) 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'
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 C6 119.05(15)
C2 C1 P1 118.82(12)
C6 C1 P1 121.99(12)
C3 C2 C1 120.68(16)
C2 C3 C4 119.74(16)
C5 C4 C3 120.13(16)
C4 C5 C6 120.38(17)
C5 C6 C1 119.99(16)
C12 C7 C8 119.60(15)
C12 C7 P1 120.57(12)
C8 C7 P1 119.80(12)
C9 C8 C7 120.07(15)
C8 C9 C10 119.97(15)
C11 C10 C9 120.29(15)
C10 C11 C12 120.04(15)
C11 C12 C7 120.02(15)
C14 C13 P1 113.50(11)
N1 C14 C15 122.42(15)
N1 C14 C13 116.46(14)
C15 C14 C13 121.11(14)
C16 C15 C14 119.30(16)
C15 C16 C17 118.71(16)
C18 C17 C16 118.36(16)
N1 C18 C17 123.97(16)
C18 N1 C14 117.25(14)
C7 P1 C1 104.35(7)
C7 P1 C13 105.51(7)
C1 P1 C13 104.58(7)
C7 P1 S1 113.74(5)
C1 P1 S1 114.46(5)
C13 P1 S1 113.22(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.394(2)
C1 C6 1.395(2)
C1 P1 1.8125(16)
C2 C3 1.381(2)
C3 C4 1.388(3)
C4 C5 1.379(3)
C5 C6 1.386(2)
C7 C12 1.390(2)
C7 C8 1.395(2)
C7 P1 1.8116(16)
C8 C9 1.383(2)
C9 C10 1.389(2)
C10 C11 1.379(2)
C11 C12 1.390(2)
C13 C14 1.501(2)
C13 P1 1.8322(15)
C14 N1 1.345(2)
C14 C15 1.389(2)
C15 C16 1.380(3)
C16 C17 1.382(3)
C17 C18 1.381(2)
C18 N1 1.336(2)
P1 S1 1.9608(6)
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
C6 C1 C2 C3 0.7(2)
P1 C1 C2 C3 176.49(13)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -0.8(3)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 1.1(3)
C2 C1 C6 C5 -1.4(2)
P1 C1 C6 C5 -177.09(13)
C12 C7 C8 C9 -0.2(2)
P1 C7 C8 C9 177.50(12)
C7 C8 C9 C10 -0.1(2)
C8 C9 C10 C11 0.0(2)
C9 C10 C11 C12 0.5(2)
C10 C11 C12 C7 -0.9(2)
C8 C7 C12 C11 0.7(2)
P1 C7 C12 C11 -176.98(12)
P1 C13 C14 N1 83.07(15)
P1 C13 C14 C15 -97.76(16)
N1 C14 C15 C16 0.2(2)
C13 C14 C15 C16 -178.93(15)
C14 C15 C16 C17 -0.5(2)
C15 C16 C17 C18 0.3(2)
C16 C17 C18 N1 0.2(3)
C17 C18 N1 C14 -0.5(2)
C15 C14 N1 C18 0.3(2)
C13 C14 N1 C18 179.47(14)
C12 C7 P1 C1 -128.09(13)
C8 C7 P1 C1 54.24(14)
C12 C7 P1 C13 121.99(13)
C8 C7 P1 C13 -55.68(14)
C12 C7 P1 S1 -2.69(14)
C8 C7 P1 S1 179.64(11)
C2 C1 P1 C7 37.54(14)
C6 C1 P1 C7 -146.80(13)
C2 C1 P1 C13 148.12(13)
C6 C1 P1 C13 -36.21(15)
C2 C1 P1 S1 -87.41(13)
C6 C1 P1 S1 88.26(13)
C14 C13 P1 C7 -69.68(13)
C14 C13 P1 C1 -179.43(11)
C14 C13 P1 S1 55.32(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659773
