#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:42:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178720 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/31/4083164.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_4083164
loop_
_publ_author_name
'Ghisolfi, Alessio'
'Fliedel, Christophe'
'Rosa, Vitor'
'Monakhov, Kirill Yu.'
'Braunstein, Pierre'
_publ_section_title
;
 Combined Experimental and Theoretical Study of
 Bis(diphenylphosphino)(N-thioether)amine-Type Ligands in Nickel(II)
 Complexes for Catalytic Ethylene Oligomerization
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2523
_journal_paper_doi               10.1021/om500141k
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C31 H27 N P2 S'
_chemical_formula_sum            'C31 H27 N P2 S'
_chemical_formula_weight         507.54
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 114.573(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3103(3)
_cell_length_b                   18.3198(9)
_cell_length_c                   9.5180(3)
_cell_measurement_reflns_used    6522
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1317.81(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7889
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.3274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                4601
_reflns_number_total             5106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500141k_si_002.cif
_cod_data_source_block           compound_4
_cod_depositor_comments
'Adding full bibliography for 4083164--4083170.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4083164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.36229(8) 0.00572(3) 0.97947(7) 0.02712(14) Uani 1 1 d .
S1 S 0.91691(9) 0.29834(4) 0.94054(8) 0.03823(17) Uani 1 1 d .
P2 P 0.70400(8) -0.05957(3) 1.00144(7) 0.02715(15) Uani 1 1 d .
N1 N 0.5752(3) 0.01585(11) 0.9924(2) 0.0265(4) Uani 1 1 d .
C26 C 0.5632(3) -0.14805(15) 1.1729(3) 0.0307(5) Uani 1 1 d .
H26 H 0.4633 -0.1561 1.0817 0.037 Uiso 1 1 calc R
C1 C 0.6546(3) 0.08537(13) 0.9839(3) 0.0245(5) Uani 1 1 d .
C4 C 0.8152(3) 0.21736(15) 0.9639(3) 0.0288(5) Uani 1 1 d .
C12 C 0.2419(3) 0.14618(15) 0.8384(3) 0.0333(6) Uani 1 1 d .
H12 H 0.3215 0.1679 0.9290 0.040 Uiso 1 1 calc R
C7 C 0.2297(3) 0.07064(14) 0.8283(3) 0.0267(5) Uani 1 1 d .
C8 C 0.1074(3) 0.03946(16) 0.6917(3) 0.0341(6) Uani 1 1 d .
H8 H 0.0959 -0.0110 0.6832 0.041 Uiso 1 1 calc R
C6 C 0.6998(3) 0.09861(15) 0.8612(3) 0.0324(6) Uani 1 1 d .
H6 H 0.6757 0.0635 0.7845 0.039 Uiso 1 1 calc R
C19 C 0.5612(3) -0.11607(15) 0.8390(3) 0.0291(5) Uani 1 1 d .
C18 C 0.5077(3) 0.03665(16) 1.2959(3) 0.0326(6) Uani 1 1 d .
H18 H 0.6071 0.0122 1.2989 0.039 Uiso 1 1 calc R
C30 C 0.8567(3) -0.09969(14) 1.3080(3) 0.0322(6) Uani 1 1 d .
H30 H 0.9544 -0.0750 1.3077 0.039 Uiso 1 1 calc R
C17 C 0.5039(4) 0.06107(17) 1.4328(3) 0.0390(7) Uani 1 1 d .
H17 H 0.6021 0.0540 1.5258 0.047 Uiso 1 1 calc R
C5 C 0.7803(4) 0.16336(16) 0.8518(3) 0.0344(6) Uani 1 1 d .
H5 H 0.8115 0.1710 0.7697 0.041 Uiso 1 1 calc R
C2 C 0.6905(3) 0.13841(15) 1.0963(3) 0.0321(6) Uani 1 1 d .
H2 H 0.6621 0.1301 1.1797 0.039 Uiso 1 1 calc R
C23 C 0.4928(5) -0.23391(18) 0.7125(4) 0.0472(8) Uani 1 1 d .
H23 H 0.5096 -0.2842 0.7163 0.057 Uiso 1 1 calc R
C9 C 0.0027(3) 0.08337(18) 0.5682(3) 0.0402(7) Uani 1 1 d .
H9 H -0.0779 0.0622 0.4774 0.048 Uiso 1 1 calc R
C20 C 0.4458(3) -0.08397(17) 0.7005(3) 0.0367(6) Uani 1 1 d .
H20 H 0.4300 -0.0336 0.6948 0.044 Uiso 1 1 calc R
C25 C 0.7045(3) -0.10850(14) 1.1695(3) 0.0282(5) Uani 1 1 d .
C31 C 0.9639(4) 0.34590(17) 1.1169(4) 0.0421(7) Uani 1 1 d .
H31A H 0.8562 0.3529 1.1296 0.063 Uiso 1 1 calc R
H31B H 1.0152 0.3925 1.1140 0.063 Uiso 1 1 calc R
H31C H 1.0454 0.3179 1.2019 0.063 Uiso 1 1 calc R
C16 C 0.3565(4) 0.0957(2) 1.4324(3) 0.0495(8) Uani 1 1 d .
H16 H 0.3539 0.1118 1.5242 0.059 Uiso 1 1 calc R
C29 C 0.8614(4) -0.12764(17) 1.4448(3) 0.0384(6) Uani 1 1 d .
H29 H 0.9620 -0.1215 1.5363 0.046 Uiso 1 1 calc R
C28 C 0.7175(4) -0.16454(17) 1.4459(3) 0.0414(7) Uani 1 1 d .
H28 H 0.7202 -0.1821 1.5386 0.050 Uiso 1 1 calc R
C13 C 0.3646(3) 0.04834(15) 1.1542(3) 0.0297(5) Uani 1 1 d .
C27 C 0.5694(4) -0.17550(17) 1.3103(3) 0.0386(6) Uani 1 1 d .
H27 H 0.4736 -0.2014 1.3113 0.046 Uiso 1 1 calc R
C22 C 0.3760(4) -0.2015(2) 0.5772(3) 0.0500(8) Uani 1 1 d .
H22 H 0.3124 -0.2300 0.4909 0.060 Uiso 1 1 calc R
C11 C 0.1374(4) 0.18931(16) 0.7155(3) 0.0367(6) Uani 1 1 d .
H11 H 0.1472 0.2399 0.7237 0.044 Uiso 1 1 calc R
C10 C 0.0182(3) 0.15789(17) 0.5803(3) 0.0376(6) Uani 1 1 d .
H10 H -0.0515 0.1872 0.4976 0.045 Uiso 1 1 calc R
C24 C 0.5851(4) -0.19170(16) 0.8426(3) 0.0374(6) Uani 1 1 d .
H24 H 0.6635 -0.2140 0.9330 0.045 Uiso 1 1 calc R
C21 C 0.3543(4) -0.1268(2) 0.5710(3) 0.0472(8) Uani 1 1 d .
H21 H 0.2779 -0.1049 0.4793 0.057 Uiso 1 1 calc R
C3 C 0.7689(4) 0.20422(15) 1.0857(3) 0.0332(6) Uani 1 1 d .
H3 H 0.7903 0.2397 1.1612 0.040 Uiso 1 1 calc R
C14 C 0.2162(4) 0.0829(2) 1.1562(3) 0.0462(8) Uani 1 1 d .
H14 H 0.1177 0.0906 1.0638 0.055 Uiso 1 1 calc R
C15 C 0.2131(4) 0.1059(2) 1.2932(4) 0.0553(9) Uani 1 1 d .
H15 H 0.1123 0.1288 1.2915 0.066 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 P1 C13 105.41(11)
N1 P1 C7 104.37(10)
C13 P1 C7 102.21(12)
C4 S1 C31 102.74(13)
N1 P2 C19 103.87(11)
N1 P2 C25 102.19(10)
C19 P2 C25 103.07(12)
C1 N1 P2 114.70(15)
C1 N1 P1 124.36(16)
P2 N1 P1 120.75(12)
C27 C26 C25 120.8(2)
C27 C26 H26 119.6
C25 C26 H26 119.6
C2 C1 C6 118.7(2)
C2 C1 N1 122.0(2)
C6 C1 N1 119.2(2)
C3 C4 C5 118.4(3)
C3 C4 S1 124.4(2)
C5 C4 S1 117.2(2)
C11 C12 C7 120.7(2)
C11 C12 H12 119.7
C7 C12 H12 119.7
C12 C7 C8 118.4(2)
C12 C7 P1 126.01(19)
C8 C7 P1 115.5(2)
C9 C8 C7 120.5(3)
C9 C8 H8 119.8
C7 C8 H8 119.8
C5 C6 C1 120.8(2)
C5 C6 H6 119.6
C1 C6 H6 119.6
C20 C19 C24 118.3(3)
C20 C19 P2 120.6(2)
C24 C19 P2 120.3(2)
C17 C18 C13 120.9(2)
C17 C18 H18 119.5
C13 C18 H18 119.5
C29 C30 C25 120.1(2)
C29 C30 H30 119.9
C25 C30 H30 119.9
C16 C17 C18 120.8(2)
C16 C17 H17 119.6
C18 C17 H17 119.6
C6 C5 C4 120.7(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C2 C3 120.6(2)
C1 C2 H2 119.7
C3 C2 H2 119.7
C22 C23 C24 120.3(3)
C22 C23 H23 119.8
C24 C23 H23 119.8
C10 C9 C8 120.0(3)
C10 C9 H9 120.0
C8 C9 H9 120.0
C21 C20 C19 120.4(3)
C21 C20 H20 119.8
C19 C20 H20 119.8
C26 C25 C30 118.5(2)
C26 C25 P2 125.40(19)
C30 C25 P2 115.9(2)
S1 C31 H31A 109.5
S1 C31 H31B 109.5
H31A C31 H31B 109.5
S1 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C15 C16 C17 118.5(3)
C15 C16 H16 120.7
C17 C16 H16 120.7
C28 C29 C30 120.2(2)
C28 C29 H29 119.9
C30 C29 H29 119.9
C29 C28 C27 120.3(3)
C29 C28 H28 119.9
C27 C28 H28 119.9
C14 C13 C18 117.4(2)
C14 C13 P1 122.1(2)
C18 C13 P1 119.7(2)
C28 C27 C26 120.1(3)
C28 C27 H27 120.0
C26 C27 H27 120.0
C21 C22 C23 119.7(3)
C21 C22 H22 120.2
C23 C22 H22 120.2
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C9 C10 C11 119.9(3)
C9 C10 H10 120.0
C11 C10 H10 120.0
C23 C24 C19 120.6(3)
C23 C24 H24 119.7
C19 C24 H24 119.7
C22 C21 C20 120.6(3)
C22 C21 H21 119.7
C20 C21 H21 119.7
C4 C3 C2 120.8(2)
C4 C3 H3 119.6
C2 C3 H3 119.6
C15 C14 C13 121.1(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C16 C15 C14 121.2(3)
C16 C15 H15 119.4
C14 C15 H15 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N1 1.732(2)
P1 C13 1.830(3)
P1 C7 1.839(2)
S1 C4 1.767(3)
S1 C31 1.784(3)
P2 N1 1.728(2)
P2 C19 1.828(3)
P2 C25 1.833(3)
N1 C1 1.452(3)
C26 C27 1.382(4)
C26 C25 1.392(4)
C26 H26 0.9300
C1 C2 1.383(3)
C1 C6 1.388(3)
C4 C3 1.386(4)
C4 C5 1.395(4)
C12 C11 1.379(4)
C12 C7 1.388(4)
C12 H12 0.9300
C7 C8 1.397(3)
C8 C9 1.391(4)
C8 H8 0.9300
C6 C5 1.383(4)
C6 H6 0.9300
C19 C20 1.398(4)
C19 C24 1.398(4)
C18 C17 1.390(4)
C18 C13 1.395(4)
C18 H18 0.9300
C30 C29 1.385(4)
C30 C25 1.406(4)
C30 H30 0.9300
C17 C16 1.378(4)
C17 H17 0.9300
C5 H5 0.9300
C2 C3 1.394(4)
C2 H2 0.9300
C23 C22 1.383(5)
C23 C24 1.390(4)
C23 H23 0.9300
C9 C10 1.372(4)
C9 H9 0.9300
C20 C21 1.391(4)
C20 H20 0.9300
C31 H31A 0.9600
C31 H31B 0.9600
C31 H31C 0.9600
C16 C15 1.378(4)
C16 H16 0.9300
C29 C28 1.378(4)
C29 H29 0.9300
C28 C27 1.378(4)
C28 H28 0.9300
C13 C14 1.393(4)
C27 H27 0.9300
C22 C21 1.378(6)
C22 H22 0.9300
C11 C10 1.381(4)
C11 H11 0.9300
C10 H10 0.9300
C24 H24 0.9300
C21 H21 0.9300
C3 H3 0.9300
C14 C15 1.381(4)
C14 H14 0.9300
C15 H15 0.9300
