#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:28:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178566 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/75/4067514.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_4067514
loop_
_publ_author_name
'Kozlov, V. A.'
'Aleksanyan, D. V.'
'Nelyubina, Yu. V.'
'Lyssenko, K. A.'
'Vasil’ev, A. A.'
'Petrovskii, P. V.'
'Odinets, I. L.'
_publ_section_title
;
 Cyclopalladation ofmeta-(Diphenylthiophosphoryloxy)benzaldimines:NCSand
 UnexpectedNCO5,6-Membered Pincer Palladium Complexes
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2054
_journal_paper_doi               10.1021/om9009894
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C25 H20 N O P S'
_chemical_formula_sum            'C25 H20 N O P S'
_chemical_formula_weight         413.45
_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                 91.406(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.108(2)
_cell_length_b                   16.831(4)
_cell_length_c                   12.130(3)
_cell_measurement_reflns_used    423
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     2063.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_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, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       '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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15717
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+1.1834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                3687
_reflns_number_total             5136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om9009894_si_002.cif
_cod_data_source_block           3b
_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 
;
_cod_original_cell_volume        2063.1(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4067514
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.07826(5) 0.69035(3) 1.16928(5) 0.03751(15) Uani 1 1 d . . .
P1 P 0.18278(5) 0.60926(3) 1.24246(5) 0.03269(15) Uani 1 1 d . . .
O1 O 0.33900(14) 0.61118(9) 1.21631(13) 0.0376(4) Uani 1 1 d . . .
C1 C 0.38497(19) 0.62070(11) 1.10937(18) 0.0313(4) Uani 1 1 d . . .
C2 C 0.3560(2) 0.56622(13) 1.0276(2) 0.0421(5) Uani 1 1 d . . .
H2A H 0.2998 0.5224 1.0422 0.051 Uiso 1 1 calc R . .
C3 C 0.4086(2) 0.57536(15) 0.9243(2) 0.0502(7) Uani 1 1 d . . .
C4 C 0.4914(3) 0.63861(16) 0.9047(2) 0.0525(7) Uani 1 1 d . . .
H4A H 0.5279 0.6452 0.8338 0.063 Uiso 1 1 calc R . .
C5 C 0.5217(3) 0.69248(14) 0.9877(2) 0.0481(6) Uani 1 1 d . . .
H5A H 0.5798 0.7355 0.9740 0.058 Uiso 1 1 calc R A .
C6 C 0.4676(2) 0.68384(12) 1.09075(17) 0.0338(5) Uani 1 1 d . . .
H6A H 0.4873 0.7210 1.1477 0.041 Uiso 1 1 calc R . .
N1' N 0.3167(4) 0.4751(2) 0.8179(3) 0.0325(7) Uiso 0.50 1 d P A 1
C7' C 0.4002(4) 0.5302(2) 0.8183(4) 0.0313(9) Uiso 0.50 1 d P A 1
H7'A H 0.4533 0.5421 0.7569 0.038 Uiso 0.50 1 calc PR A 1
C8' C 0.3058(5) 0.4247(3) 0.7241(4) 0.0307(9) Uiso 0.50 1 d P A 1
C9' C 0.2621(5) 0.3479(3) 0.7446(4) 0.0396(11) Uiso 0.50 1 d P A 1
H9'A H 0.2410 0.3325 0.8174 0.047 Uiso 0.50 1 calc PR A 1
C11' C 0.2742(5) 0.3092(3) 0.5579(4) 0.0307(12) Uiso 0.50 1 d P A 1
H11A H 0.2659 0.2695 0.5026 0.037 Uiso 0.50 1 calc PR A 1
C12' C 0.3165(6) 0.3922(4) 0.5312(5) 0.0554(14) Uiso 0.50 1 d P A 1
H12A H 0.3334 0.4074 0.4575 0.066 Uiso 0.50 1 calc PR A 1
C13' C 0.3306(5) 0.4468(3) 0.6177(4) 0.0419(10) Uiso 0.50 1 d P A 1
H13A H 0.3575 0.4997 0.6026 0.050 Uiso 0.50 1 calc PR A 1
C10' C 0.2495(5) 0.2945(4) 0.6598(4) 0.0432(12) Uiso 0.50 1 d P A 1
H10A H 0.2203 0.2424 0.6773 0.052 Uiso 0.50 1 calc PR A 1
C13 C 0.4045(5) 0.4371(3) 0.5854(4) 0.0418(10) Uiso 0.50 1 d P A 2
H13B H 0.4630 0.4776 0.5621 0.050 Uiso 0.50 1 calc PR A 2
C10 C 0.2294(6) 0.3210(4) 0.6438(5) 0.0574(17) Uiso 0.50 1 d P A 2
H10B H 0.1704 0.2796 0.6628 0.069 Uiso 0.50 1 calc PR A 2
C12 C 0.3709(6) 0.3756(3) 0.5144(5) 0.0501(13) Uiso 0.50 1 d P A 2
H12B H 0.4134 0.3720 0.4456 0.060 Uiso 0.50 1 calc PR A 2
N1 N 0.3948(3) 0.50335(19) 0.7583(3) 0.0277(7) Uiso 0.50 1 d P A 2
C7 C 0.3602(4) 0.5035(2) 0.8566(3) 0.0273(8) Uiso 0.50 1 d P A 2
H7A H 0.3080 0.4624 0.8870 0.033 Uiso 0.50 1 calc PR A 2
C8 C 0.3544(4) 0.4400(2) 0.6883(4) 0.0279(8) Uiso 0.50 1 d P A 2
C9 C 0.2647(6) 0.3817(4) 0.7189(5) 0.0513(13) Uiso 0.50 1 d P A 2
H9A H 0.2274 0.3828 0.7900 0.062 Uiso 0.50 1 calc PR A 2
C11 C 0.2870(6) 0.3251(4) 0.5378(5) 0.0395(15) Uiso 0.50 1 d P A 2
H11B H 0.2599 0.2877 0.4832 0.047 Uiso 0.50 1 calc PR A 2
C14 C 0.1938(2) 0.61664(12) 1.39010(19) 0.0369(5) Uani 1 1 d . . .
C15 C 0.3039(3) 0.64945(16) 1.4448(2) 0.0536(7) Uani 1 1 d . . .
H15A H 0.3789 0.6650 1.4044 0.064 Uiso 1 1 calc R . .
C16 C 0.3037(3) 0.65936(19) 1.5579(2) 0.0673(9) Uani 1 1 d . . .
H16A H 0.3784 0.6822 1.5949 0.081 Uiso 1 1 calc R . .
C17 C 0.1955(3) 0.63630(15) 1.6172(2) 0.0578(7) Uani 1 1 d . . .
H17A H 0.1964 0.6430 1.6950 0.069 Uiso 1 1 calc R . .
C18 C 0.0863(3) 0.60367(13) 1.5644(2) 0.0475(6) Uani 1 1 d . . .
H18A H 0.0120 0.5879 1.6056 0.057 Uiso 1 1 calc R . .
C19 C 0.0849(2) 0.59383(13) 1.45063(19) 0.0414(5) Uani 1 1 d . . .
H19A H 0.0095 0.5715 1.4141 0.050 Uiso 1 1 calc R . .
C20 C 0.13044(19) 0.50889(12) 1.21102(17) 0.0320(4) Uani 1 1 d . . .
C21 C 0.2096(2) 0.44564(14) 1.2456(2) 0.0467(6) Uani 1 1 d . . .
H21A H 0.2883 0.4554 1.2880 0.056 Uiso 1 1 calc R . .
C22 C 0.1739(2) 0.36844(14) 1.2185(2) 0.0498(6) Uani 1 1 d . . .
H22A H 0.2282 0.3253 1.2421 0.060 Uiso 1 1 calc R . .
C23 C 0.0599(2) 0.35419(13) 1.15723(19) 0.0397(5) Uani 1 1 d . . .
H23A H 0.0360 0.3012 1.1384 0.048 Uiso 1 1 calc R . .
C24 C -0.0196(2) 0.41649(13) 1.1231(2) 0.0425(5) Uani 1 1 d . . .
H24A H -0.0984 0.4064 1.0810 0.051 Uiso 1 1 calc R . .
C25 C 0.0154(2) 0.49405(13) 1.15010(19) 0.0399(5) Uani 1 1 d . . .
H25A H -0.0396 0.5369 1.1268 0.048 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'
O O 0.0106 0.0060 '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
O1 P1 C14 99.05(9)
O1 P1 C20 105.02(9)
C14 P1 C20 106.59(10)
O1 P1 S1 114.94(6)
C14 P1 S1 115.45(8)
C20 P1 S1 114.20(7)
C1 O1 P1 122.16(12)
C6 C1 C2 121.1(2)
C6 C1 O1 117.29(18)
C2 C1 O1 121.49(19)
C1 C2 C3 119.9(2)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
C4 C3 C2 119.5(2)
C4 C3 C7' 105.4(3)
C2 C3 C7' 135.1(3)
C4 C3 C7 134.6(3)
C2 C3 C7 105.8(3)
C3 C4 C5 120.3(2)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C4 C5 C6 120.2(2)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C1 C6 C5 119.0(2)
C1 C6 H6A 120.5
C5 C6 H6A 120.5
C7' N1' C8' 118.9(4)
N1' C7' C3 113.8(4)
N1' C7' H7'A 123.1
C3 C7' H7'A 123.1
C13' C8' C9' 119.1(4)
C13' C8' N1' 125.3(4)
C9' C8' N1' 115.5(4)
C10' C9' C8' 120.0(5)
C10' C9' H9'A 120.0
C8' C9' H9'A 120.0
C10' C11' C12' 116.7(5)
C10' C11' H11A 121.7
C12' C11' H11A 121.7
C13' C12' C11' 118.3(5)
C13' C12' H12A 120.8
C11' C12' H12A 120.8
C8' C13' C12' 120.6(5)
C8' C13' H13A 119.7
C12' C13' H13A 119.7
C11' C10' C9' 125.1(6)
C11' C10' H10A 117.4
C9' C10' H10A 117.4
C8 C13 C12 120.5(5)
C8 C13 H13B 119.8
C12 C13 H13B 119.8
C9 C10 C11 116.5(6)
C9 C10 H10B 121.8
C11 C10 H10B 121.8
C11 C12 C13 122.0(6)
C11 C12 H12B 119.0
C13 C12 H12B 119.0
C7 N1 C8 119.3(4)
N1 C7 C3 114.8(4)
N1 C7 H7A 122.6
C3 C7 H7A 122.6
C13 C8 C9 118.6(4)
C13 C8 N1 118.0(4)
C9 C8 N1 123.4(5)
C8 C9 C10 119.7(5)
C8 C9 H9A 120.2
C10 C9 H9A 120.2
C12 C11 C10 122.5(6)
C12 C11 H11B 118.8
C10 C11 H11B 118.8
C19 C14 C15 119.3(2)
C19 C14 P1 118.47(17)
C15 C14 P1 122.06(18)
C16 C15 C14 120.0(2)
C16 C15 H15A 120.0
C14 C15 H15A 120.0
C15 C16 C17 120.3(3)
C15 C16 H16A 119.8
C17 C16 H16A 119.8
C18 C17 C16 120.4(3)
C18 C17 H17A 119.8
C16 C17 H17A 119.8
C17 C18 C19 119.9(2)
C17 C18 H18A 120.1
C19 C18 H18A 120.1
C18 C19 C14 120.2(2)
C18 C19 H19A 119.9
C14 C19 H19A 119.9
C25 C20 C21 119.5(2)
C25 C20 P1 121.23(15)
C21 C20 P1 119.24(16)
C22 C21 C20 120.1(2)
C22 C21 H21A 119.9
C20 C21 H21A 119.9
C23 C22 C21 120.1(2)
C23 C22 H22A 120.0
C21 C22 H22A 120.0
C22 C23 C24 120.3(2)
C22 C23 H23A 119.9
C24 C23 H23A 119.9
C23 C24 C25 120.0(2)
C23 C24 H24A 120.0
C25 C24 H24A 120.0
C20 C25 C24 120.1(2)
C20 C25 H25A 120.0
C24 C25 H25A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 P1 1.9289(8)
P1 O1 1.6185(16)
P1 C14 1.796(2)
P1 C20 1.808(2)
O1 C1 1.398(3)
C1 C6 1.374(3)
C1 C2 1.377(3)
C2 C3 1.382(4)
C2 H2A 0.9500
C3 C4 1.379(4)
C3 C7' 1.495(5)
C3 C7 1.535(5)
C4 C5 1.384(3)
C4 H4A 0.9500
C5 C6 1.384(3)
C5 H5A 0.9500
C6 H6A 0.9500
N1' C7' 1.253(6)
N1' C8' 1.422(5)
C7' H7'A 0.9500
C8' C13' 1.372(7)
C8' C9' 1.390(7)
C9' C10' 1.370(7)
C9' H9'A 0.9500
C11' C10' 1.290(8)
C11' C12' 1.499(8)
C11' H11A 0.9500
C12' C13' 1.398(8)
C12' H12A 0.9500
C13' H13A 0.9500
C10' H10A 0.9500
C13 C8 1.359(7)
C13 C12 1.383(7)
C13 H13B 0.9500
C10 C9 1.407(9)
C10 C11 1.426(9)
C10 H10B 0.9500
C12 C11 1.239(8)
C12 H12B 0.9500
N1 C7 1.251(5)
N1 C8 1.417(5)
C7 H7A 0.9500
C8 C9 1.393(7)
C9 H9A 0.9500
C11 H11B 0.9500
C14 C19 1.391(3)
C14 C15 1.396(3)
C15 C16 1.381(4)
C15 H15A 0.9500
C16 C17 1.380(4)
C16 H16A 0.9500
C17 C18 1.377(4)
C17 H17A 0.9500
C18 C19 1.390(3)
C18 H18A 0.9500
C19 H19A 0.9500
C20 C25 1.385(3)
C20 C21 1.390(3)
C21 C22 1.386(3)
C21 H21A 0.9500
C22 C23 1.376(3)
C22 H22A 0.9500
C23 C24 1.379(3)
C23 H23A 0.9500
C24 C25 1.390(3)
C24 H24A 0.9500
C25 H25A 0.9500
