#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:15:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178695 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/06/4080690.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_4080690
loop_
_publ_author_name
'Leung, Wing-Por'
'Chan, Yuk-Chi'
'Mak, Thomas C. W.'
_publ_section_title
;
 Synthesis and Structural Characterization of Lithium, Potassium,
 Magnesium, and Heavier Group 14 Metal Complexes Derived from
 2-Quinolyl-Linked (Thiophosphorano)methane
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2584
_journal_paper_doi               10.1021/om400062e
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C16 H21 K N P S'
_chemical_formula_weight         329.47
_chemical_name_systematic
; 
 ? 
;
_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                 105.8950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8842(9)
_cell_length_b                   9.9351(7)
_cell_length_c                   13.9787(10)
_cell_measurement_reflns_used    77
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1720.9(2)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_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  0.0756
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18758
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0429
_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)+(0.0529P)²+0.9384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2224
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400062e_si_002.cif
_cod_data_source_block           CYC26
_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 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4080690
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
K1 K 0.62775(6) 0.09623(7) -0.40523(6) 0.0534(2) Uani 1 1 d .
S1 S 0.60165(7) 0.01252(8) -0.62868(7) 0.0531(3) Uani 1 1 d .
P1 P 0.64426(6) -0.18103(8) -0.61249(6) 0.0376(2) Uani 1 1 d .
N1 N 0.65928(18) -0.1846(2) -0.38309(17) 0.0337(5) Uani 1 1 d .
C1 C 0.6697(2) -0.1857(3) -0.2835(2) 0.0334(6) Uani 1 1 d .
C2 C 0.7444(2) -0.0958(3) -0.2216(2) 0.0422(7) Uani 1 1 d .
H2A H 0.8154 -0.1181 -0.2303 0.051 Uiso 1 1 calc R
C3 C 0.7572(3) -0.0912(3) -0.1207(2) 0.0496(8) Uani 1 1 d .
H3A H 0.8067 -0.0315 -0.0818 0.060 Uiso 1 1 calc R
C4 C 0.6973(3) -0.1744(4) -0.0760(3) 0.0577(9) Uani 1 1 d .
H4A H 0.7063 -0.1703 -0.0077 0.069 Uiso 1 1 calc R
C5 C 0.6245(3) -0.2629(3) -0.1341(2) 0.0505(8) Uani 1 1 d .
H5A H 0.5852 -0.3196 -0.1041 0.061 Uiso 1 1 calc R
C6 C 0.6083(2) -0.2694(3) -0.2370(2) 0.0379(7) Uani 1 1 d .
C7 C 0.5308(2) -0.3549(3) -0.3014(2) 0.0412(7) Uani 1 1 d .
H7A H 0.4872 -0.4105 -0.2754 0.049 Uiso 1 1 calc R
C8 C 0.5208(2) -0.3554(3) -0.3995(2) 0.0377(7) Uani 1 1 d .
H8A H 0.4698 -0.4113 -0.4407 0.045 Uiso 1 1 calc R
C9 C 0.5879(2) -0.2704(3) -0.4424(2) 0.0333(6) Uani 1 1 d .
C10 C 0.5773(2) -0.2793(3) -0.5449(2) 0.0370(7) Uani 1 1 d .
H10A H 0.5298 -0.3439 -0.5801 0.044 Uiso 1 1 calc R
C11 C 0.6112(3) -0.2621(4) -0.7356(2) 0.0547(9) Uani 1 1 d .
H11A H 0.6322 -0.3570 -0.7253 0.066 Uiso 1 1 calc R
C12 C 0.6726(4) -0.2016(5) -0.8043(3) 0.0843(14) Uani 1 1 d .
H12A H 0.6532 -0.2482 -0.8669 0.127 Uiso 1 1 calc R
H12B H 0.7488 -0.2104 -0.7744 0.127 Uiso 1 1 calc R
H12C H 0.6543 -0.1081 -0.8151 0.127 Uiso 1 1 calc R
C13 C 0.4902(3) -0.2578(5) -0.7853(3) 0.0872(14) Uani 1 1 d .
H13A H 0.4750 -0.3017 -0.8488 0.131 Uiso 1 1 calc R
H13B H 0.4667 -0.1658 -0.7944 0.131 Uiso 1 1 calc R
H13C H 0.4527 -0.3031 -0.7441 0.131 Uiso 1 1 calc R
C14 C 0.7900(3) -0.1990(3) -0.5540(3) 0.0508(8) Uani 1 1 d .
H14A H 0.7979 -0.1908 -0.4825 0.061 Uiso 1 1 calc R
C15 C 0.8602(3) -0.0883(4) -0.5770(4) 0.0809(13) Uani 1 1 d .
H15A H 0.9344 -0.1061 -0.5429 0.121 Uiso 1 1 calc R
H15B H 0.8392 -0.0035 -0.5552 0.121 Uiso 1 1 calc R
H15C H 0.8517 -0.0852 -0.6473 0.121 Uiso 1 1 calc R
C16 C 0.8318(3) -0.3391(4) -0.5668(3) 0.0727(11) Uani 1 1 d .
H16A H 0.9078 -0.3433 -0.5347 0.109 Uiso 1 1 calc R
H16B H 0.8192 -0.3582 -0.6364 0.109 Uiso 1 1 calc R
H16C H 0.7947 -0.4043 -0.5375 0.109 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'
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'
K K 0.2009 0.2494 '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
N1 K1 C10 133.38(7) . 3_654
N1 K1 S1 79.72(5) . .
C10 K1 S1 94.47(6) 3_654 .
N1 K1 C2 46.04(7) . .
C10 K1 C2 134.76(8) 3_654 .
S1 K1 C2 122.14(6) . .
N1 K1 C1 24.71(6) . .
C10 K1 C1 128.94(7) 3_654 .
S1 K1 C1 104.40(5) . .
C2 K1 C1 25.38(7) . .
N1 K1 C4 128.06(8) . 2_654
C10 K1 C4 97.80(8) 3_654 2_654
S1 K1 C4 89.61(7) . 2_654
C2 K1 C4 107.19(8) . 2_654
C1 K1 C4 128.69(8) . 2_654
N1 K1 S1 76.61(5) . 3_654
C10 K1 S1 59.14(5) 3_654 3_654
S1 K1 S1 101.47(3) . 3_654
C2 K1 S1 86.13(6) . 3_654
C1 K1 S1 70.68(5) . 3_654
C4 K1 S1 154.79(7) 2_654 3_654
N1 K1 C5 106.83(8) . 2_654
C10 K1 C5 119.79(8) 3_654 2_654
S1 K1 C5 96.29(6) . 2_654
C2 K1 C5 84.38(8) . 2_654
C1 K1 C5 104.92(8) . 2_654
C4 K1 C5 23.78(8) 2_654 2_654
S1 K1 C5 162.25(6) 3_654 2_654
N1 K1 C3 147.24(8) . 2_654
C10 K1 C3 79.07(8) 3_654 2_654
S1 K1 C3 105.65(6) . 2_654
C2 K1 C3 111.06(8) . 2_654
C1 K1 C3 136.36(8) . 2_654
C4 K1 C3 23.88(8) 2_654 2_654
S1 K1 C3 131.42(6) 3_654 2_654
C5 K1 C3 41.03(8) 2_654 2_654
N1 K1 C9 128.89(7) . 3_654
C10 K1 C9 23.89(7) 3_654 3_654
S1 K1 C9 70.94(5) . 3_654
C2 K1 C9 155.00(8) . 3_654
C1 K1 C9 138.05(7) . 3_654
C4 K1 C9 93.25(8) 2_654 3_654
S1 K1 C9 69.71(5) 3_654 3_654
C5 K1 C9 117.01(8) 2_654 3_654
C3 K1 C9 82.11(7) 2_654 3_654
N1 K1 P1 109.27(5) . 3_654
C10 K1 P1 28.22(5) 3_654 3_654
S1 K1 P1 106.35(3) . 3_654
C2 K1 P1 109.11(6) . 3_654
C1 K1 P1 100.79(5) . 3_654
C4 K1 P1 122.47(7) 2_654 3_654
S1 K1 P1 32.66(2) 3_654 3_654
C5 K1 P1 140.07(6) 2_654 3_654
C3 K1 P1 100.27(6) 2_654 3_654
C9 K1 P1 46.28(5) 3_654 3_654
N1 K1 K1 71.05(5) . 3_654
C10 K1 K1 69.28(6) 3_654 3_654
S1 K1 K1 52.26(2) . 3_654
C2 K1 K1 110.89(6) . 3_654
C1 K1 K1 85.70(5) . 3_654
C4 K1 K1 136.45(7) 2_654 3_654
S1 K1 K1 49.20(2) 3_654 3_654
C5 K1 K1 148.55(6) 2_654 3_654
C3 K1 K1 137.92(6) 2_654 3_654
C9 K1 K1 57.85(5) 3_654 3_654
P1 K1 K1 62.49(2) 3_654 3_654
P1 S1 K1 100.95(4) . .
P1 S1 K1 84.12(4) . 3_654
K1 S1 K1 78.53(3) . 3_654
C10 P1 C14 107.54(15) . .
C10 P1 C11 103.87(14) . .
C14 P1 C11 108.62(16) . .
C10 P1 S1 116.07(10) . .
C14 P1 S1 111.06(11) . .
C11 P1 S1 109.26(12) . .
C10 P1 K1 57.94(9) . 3_654
C14 P1 K1 150.17(11) . 3_654
C11 P1 K1 100.52(12) . 3_654
S1 P1 K1 63.22(3) . 3_654
C9 N1 C1 118.7(2) . .
C9 N1 K1 120.02(17) . .
C1 N1 K1 95.21(16) . .
N1 C1 C2 118.5(3) . .
N1 C1 C6 124.1(3) . .
C2 C1 C6 117.3(3) . .
N1 C1 K1 60.08(14) . .
C2 C1 K1 76.36(16) . .
C6 C1 K1 135.31(18) . .
C3 C2 C1 121.1(3) . .
C3 C2 K1 134.1(2) . .
C1 C2 K1 78.26(16) . .
C2 C3 C4 121.1(3) . .
C2 C3 K1 90.31(19) . 2_644
C4 C3 K1 72.0(2) . 2_644
C5 C4 C3 119.1(3) . .
C5 C4 K1 83.1(2) . 2_644
C3 C4 K1 84.2(2) . 2_644
C4 C5 C6 121.5(3) . .
C4 C5 K1 73.1(2) . 2_644
C6 C5 K1 90.96(19) . 2_644
C5 C6 C1 119.9(3) . .
C5 C6 C7 124.0(3) . .
C1 C6 C7 116.1(3) . .
C8 C7 C6 120.2(3) . .
C7 C8 C9 121.3(3) . .
N1 C9 C10 121.5(2) . .
N1 C9 C8 119.6(2) . .
C10 C9 C8 118.9(3) . .
N1 C9 K1 110.92(16) . 3_654
C10 C9 K1 64.31(15) . 3_654
C8 C9 K1 94.40(16) . 3_654
C9 C10 P1 126.5(2) . .
C9 C10 K1 91.80(17) . 3_654
P1 C10 K1 93.84(11) . 3_654
C13 C11 C12 110.1(3) . .
C13 C11 P1 111.1(3) . .
C12 C11 P1 112.9(3) . .
C15 C14 C16 112.8(3) . .
C15 C14 P1 115.6(3) . .
C16 C14 P1 112.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 N1 2.825(2) .
K1 C10 3.124(3) 3_654
K1 S1 3.1600(12) .
K1 C2 3.221(3) .
K1 C1 3.245(3) .
K1 C4 3.266(4) 2_654
K1 S1 3.3009(11) 3_654
K1 C5 3.390(3) 2_654
K1 C3 3.417(3) 2_654
K1 C9 3.465(3) 3_654
K1 P1 3.6782(11) 3_654
K1 K1 4.0909(15) 3_654
S1 P1 1.9956(11) .
S1 K1 3.3010(11) 3_654
P1 C10 1.743(3) .
P1 C14 1.839(3) .
P1 C11 1.841(3) .
P1 K1 3.6782(11) 3_654
N1 C9 1.357(3) .
N1 C1 1.362(3) .
C1 C2 1.421(4) .
C1 C6 1.422(4) .
C2 C3 1.375(4) .
C3 C4 1.391(5) .
C3 K1 3.417(3) 2_644
C4 C5 1.377(5) .
C4 K1 3.266(4) 2_644
C5 C6 1.397(4) .
C5 K1 3.390(3) 2_644
C6 C7 1.427(4) .
C7 C8 1.341(4) .
C8 C9 1.450(4) .
C9 C10 1.404(4) .
C9 K1 3.465(3) 3_654
C10 K1 3.124(3) 3_654
C11 C13 1.524(5) .
C11 C12 1.525(5) .
C14 C15 1.513(5) .
C14 C16 1.521(5) .
