#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/06/4080685.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_4080685
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 H22 N P S'
_chemical_formula_weight         291.38
_chemical_name_systematic
; 
 ? 
;
_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                 112.9150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6310(4)
_cell_length_b                   12.1927(4)
_cell_length_c                   12.3190(4)
_cell_measurement_reflns_used    153
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1609.13(9)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15261
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0322
_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)+(0.0521P)²+0.4394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2485
_reflns_number_total             2866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400062e_si_002.cif
_cod_data_source_block           CYC14
_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)/c
_cod_database_code               4080685
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
P1 P 0.21008(4) 0.19400(3) 0.21564(4) 0.04032(14) Uani 1 1 d .
S1 S 0.27434(5) 0.15842(4) 0.09442(4) 0.05771(17) Uani 1 1 d .
N1 N 0.27956(14) -0.01845(12) 0.44816(12) 0.0503(4) Uani 1 1 d .
C1 C 0.29727(16) -0.12863(16) 0.46869(15) 0.0524(4) Uani 1 1 d .
C2 C 0.2431(2) -0.1792(2) 0.5404(2) 0.0726(6) Uani 1 1 d .
H2A H 0.1977 -0.1373 0.5729 0.087 Uiso 1 1 calc R
C3 C 0.2571(3) -0.2887(2) 0.5624(3) 0.0906(8) Uani 1 1 d .
H3A H 0.2209 -0.3211 0.6097 0.109 Uiso 1 1 calc R
C4 C 0.3253(3) -0.3534(2) 0.5144(3) 0.0946(9) Uani 1 1 d .
H4A H 0.3331 -0.4283 0.5294 0.113 Uiso 1 1 calc R
C5 C 0.3803(2) -0.30716(18) 0.4459(2) 0.0780(7) Uani 1 1 d .
H5A H 0.4261 -0.3505 0.4151 0.094 Uiso 1 1 calc R
C6 C 0.36767(18) -0.19297(15) 0.42169(17) 0.0560(5) Uani 1 1 d .
C7 C 0.42460(18) -0.13890(16) 0.35459(18) 0.0583(5) Uani 1 1 d .
H7A H 0.4731 -0.1780 0.3231 0.070 Uiso 1 1 calc R
C8 C 0.40806(17) -0.02913(15) 0.33627(16) 0.0531(4) Uani 1 1 d .
H8A H 0.4460 0.0078 0.2930 0.064 Uiso 1 1 calc R
C9 C 0.33297(15) 0.02841(14) 0.38342(14) 0.0445(4) Uani 1 1 d .
C10 C 0.31254(17) 0.14977(14) 0.36363(14) 0.0485(4) Uani 1 1 d .
H10A H 0.3933 0.1843 0.3830 0.058 Uiso 1 1 calc R
H10B H 0.2785 0.1774 0.4187 0.058 Uiso 1 1 calc R
C11 C 0.05386(17) 0.13713(16) 0.18119(16) 0.0538(4) Uani 1 1 d .
H11A H 0.0000 0.1690 0.1053 0.065 Uiso 1 1 calc R
C12 C -0.0029(2) 0.1707(2) 0.2695(2) 0.0836(7) Uani 1 1 d .
H12A H -0.0845 0.1389 0.2466 0.125 Uiso 1 1 calc R
H12B H -0.0094 0.2492 0.2705 0.125 Uiso 1 1 calc R
H12C H 0.0495 0.1452 0.3467 0.125 Uiso 1 1 calc R
C13 C 0.0496(2) 0.01346(17) 0.16281(19) 0.0704(6) Uani 1 1 d .
H13A H -0.0338 -0.0125 0.1445 0.106 Uiso 1 1 calc R
H13B H 0.1056 -0.0215 0.2335 0.106 Uiso 1 1 calc R
H13C H 0.0744 -0.0036 0.0989 0.106 Uiso 1 1 calc R
C14 C 0.19504(18) 0.34204(14) 0.23420(17) 0.0504(4) Uani 1 1 d .
H14A H 0.1657 0.3525 0.2981 0.060 Uiso 1 1 calc R
C15 C 0.3187(2) 0.40127(18) 0.2680(3) 0.0846(7) Uani 1 1 d .
H15A H 0.3070 0.4781 0.2773 0.127 Uiso 1 1 calc R
H15B H 0.3502 0.3912 0.2072 0.127 Uiso 1 1 calc R
H15C H 0.3774 0.3721 0.3409 0.127 Uiso 1 1 calc R
C16 C 0.0985(2) 0.39207(17) 0.1227(2) 0.0702(6) Uani 1 1 d .
H16A H 0.0915 0.4692 0.1344 0.105 Uiso 1 1 calc R
H16B H 0.0191 0.3575 0.1053 0.105 Uiso 1 1 calc R
H16C H 0.1240 0.3810 0.0582 0.105 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 P1 C11 108.76(9)
C10 P1 C14 102.86(8)
C11 P1 C14 105.47(9)
C10 P1 S1 113.60(6)
C11 P1 S1 112.16(7)
C14 P1 S1 113.28(6)
C9 N1 C1 117.74(16)
N1 C1 C2 118.23(19)
N1 C1 C6 122.69(17)
C2 C1 C6 119.08(19)
C3 C2 C1 120.4(3)
C2 C3 C4 120.8(2)
C5 C4 C3 120.5(2)
C4 C5 C6 120.0(3)
C7 C6 C1 117.47(17)
C7 C6 C5 123.3(2)
C1 C6 C5 119.2(2)
C8 C7 C6 119.36(18)
C7 C8 C9 119.49(18)
N1 C9 C8 123.20(16)
N1 C9 C10 116.30(15)
C8 C9 C10 120.48(16)
C9 C10 P1 116.90(12)
C13 C11 C12 111.88(17)
C13 C11 P1 112.38(14)
C12 C11 P1 113.38(15)
C15 C14 C16 110.16(18)
C15 C14 P1 112.10(14)
C16 C14 P1 110.74(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C10 1.8283(17)
P1 C11 1.8336(18)
P1 C14 1.8363(17)
P1 S1 1.9612(6)
N1 C9 1.317(2)
N1 C1 1.368(2)
C1 C2 1.411(3)
C1 C6 1.411(3)
C2 C3 1.360(4)
C3 C4 1.402(4)
C4 C5 1.363(4)
C5 C6 1.419(3)
C6 C7 1.408(3)
C7 C8 1.358(3)
C8 C9 1.410(2)
C9 C10 1.503(2)
C11 C13 1.523(3)
C11 C12 1.532(3)
C14 C15 1.516(3)
C14 C16 1.522(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659881
