#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/68/2236811.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236811
loop_
_publ_author_name
'Sewpersad, Shirveen'
'Van Zyl, Werner E.'
_publ_section_title
;
 Bis[O-propan-2-yl
 (4-ethoxyphenyl)dithiophosphonato-κ²S,S']nickel(II)
;
_journal_coeditor_code           BH2460
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1457
_journal_paper_doi               10.1107/S1600536812045114
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C11 H16 O2 P S2)2]'
_chemical_formula_moiety         'C22 H32 Ni O4 P2 S4'
_chemical_formula_sum            'C22 H32 Ni O4 P2 S4'
_chemical_formula_weight         609.37
_chemical_melting_point          441
_chemical_name_systematic
;
Bis[O-propan-2-yl
(4-ethoxyphenyl)dithiophosphonato-κ²S,S']nickel(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                109.530(4)
_cell_angle_beta                 101.959(4)
_cell_angle_gamma                93.913(5)
_cell_formula_units_Z            1
_cell_length_a                   7.8893(6)
_cell_length_b                   8.4178(7)
_cell_length_c                   11.4825(10)
_cell_measurement_reflns_used    14410
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.60
_cell_volume                     695.22(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1.2° φ scans and ω 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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14410
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.8568
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.305
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0303
_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)+(0.0280P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                2381
_reflns_number_total             3062
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2460.cif
_cod_data_source_block           I
_cod_database_code               2236811
_cod_database_fobs_code          2236811
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Ni Ni1 0.5000 0.5000 0.0000 0.02229(10) Uani d S 1 2
S S1 0.64099(6) 0.75272(6) 0.02356(5) 0.02729(13) Uani d . 1 1
S S2 0.58144(7) 0.38847(6) -0.18193(5) 0.02842(13) Uani d . 1 1
P P1 0.64598(6) 0.63370(6) -0.15849(5) 0.02271(12) Uani d . 1 1
O O1 0.19743(19) 0.8621(2) -0.53641(14) 0.0416(4) Uani d . 1 1
O O2 0.82744(15) 0.67472(17) -0.18857(12) 0.0266(3) Uani d . 1 1
C C1 0.5013(2) 0.7025(2) -0.26799(17) 0.0231(4) Uani d . 1 1
C C2 0.4982(3) 0.8752(3) -0.2422(2) 0.0317(5) Uani d . 1 1
H H2 0.5664 0.9551 -0.1634 0.038 Uiso calc R 1 1
C C3 0.3977(3) 0.9335(3) -0.3289(2) 0.0336(5) Uani d . 1 1
H H3 0.3976 1.0523 -0.3099 0.040 Uiso calc R 1 1
C C4 0.2974(2) 0.8179(3) -0.44330(19) 0.0308(5) Uani d . 1 1
C C5 0.2947(3) 0.6447(3) -0.4682(2) 0.0405(6) Uani d . 1 1
H H5 0.2227 0.5647 -0.5455 0.049 Uiso calc R 1 1
C C6 0.3960(3) 0.5880(3) -0.3815(2) 0.0360(5) Uani d . 1 1
H H6 0.3937 0.4690 -0.3996 0.043 Uiso calc R 1 1
C C7 0.2176(3) 1.0381(3) -0.5253(2) 0.0463(6) Uani d . 1 1
H H7A 0.3430 1.0834 -0.5079 0.056 Uiso calc R 1 1
H H7B 0.1696 1.1073 -0.4548 0.056 Uiso calc R 1 1
C C8 0.1178(3) 1.0441(4) -0.6510(3) 0.0654(8) Uani d . 1 1
H H8A 0.1653 0.9734 -0.7200 0.098 Uiso calc R 1 1
H H8B 0.1299 1.1621 -0.6482 0.098 Uiso calc R 1 1
H H8C -0.0063 1.0008 -0.6662 0.098 Uiso calc R 1 1
C C9 0.9927(2) 0.6387(3) -0.11992(19) 0.0302(5) Uani d . 1 1
H H9 0.9693 0.6009 -0.0502 0.036 Uiso calc R 1 1
C C10 1.1185(3) 0.8017(3) -0.0629(3) 0.0646(8) Uani d . 1 1
H H10A 1.1334 0.8447 -0.1302 0.097 Uiso calc R 1 1
H H10B 1.2319 0.7811 -0.0211 0.097 Uiso calc R 1 1
H H10C 1.0725 0.8863 0.0001 0.097 Uiso calc R 1 1
C C11 1.0541(3) 0.4983(3) -0.2128(2) 0.0567(7) Uani d . 1 1
H H11A 0.9642 0.3971 -0.2481 0.085 Uiso calc R 1 1
H H11B 1.1628 0.4711 -0.1695 0.085 Uiso calc R 1 1
H H11C 1.0758 0.5343 -0.2819 0.085 Uiso calc R 1 1
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'
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'
Ni Ni 0.3393 1.1124 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
S2 Ni1 S2 . 2_665 180.0
S2 Ni1 S1 . 2_665 91.679(18)
S2 Ni1 S1 2_665 2_665 88.321(18)
S2 Ni1 S1 . . 88.321(18)
S2 Ni1 S1 2_665 . 91.679(18)
S1 Ni1 S1 2_665 . 180.0
S2 Ni1 P1 . . 44.885(16)
S2 Ni1 P1 2_665 . 135.115(17)
S1 Ni1 P1 2_665 . 135.174(16)
S1 Ni1 P1 . . 44.827(16)
S2 Ni1 P1 . 2_665 135.115(16)
S2 Ni1 P1 2_665 2_665 44.885(16)
S1 Ni1 P1 2_665 2_665 44.827(16)
S1 Ni1 P1 . 2_665 135.173(16)
P1 Ni1 P1 . 2_665 180.0
P1 S1 Ni1 . . 83.26(2)
P1 S2 Ni1 . . 83.33(2)
O2 P1 C1 . . 100.70(7)
O2 P1 S1 . . 113.76(6)
C1 P1 S1 . . 113.38(7)
O2 P1 S2 . . 114.16(6)
C1 P1 S2 . . 113.47(7)
S1 P1 S2 . . 101.93(3)
O2 P1 Ni1 . . 141.40(5)
C1 P1 Ni1 . . 117.90(6)
S1 P1 Ni1 . . 51.913(17)
S2 P1 Ni1 . . 51.790(18)
C4 O1 C7 . . 118.46(17)
C9 O2 P1 . . 121.36(11)
C6 C1 C2 . . 118.40(18)
C6 C1 P1 . . 121.83(15)
C2 C1 P1 . . 119.72(15)
C3 C2 C1 . . 121.31(19)
C3 C2 H2 . . 119.3
C1 C2 H2 . . 119.3
C4 C3 C2 . . 119.60(19)
C4 C3 H3 . . 120.2
C2 C3 H3 . . 120.2
O1 C4 C3 . . 124.21(19)
O1 C4 C5 . . 116.20(19)
C3 C4 C5 . . 119.59(18)
C6 C5 C4 . . 120.3(2)
C6 C5 H5 . . 119.8
C4 C5 H5 . . 119.8
C5 C6 C1 . . 120.7(2)
C5 C6 H6 . . 119.6
C1 C6 H6 . . 119.6
O1 C7 C8 . . 106.7(2)
O1 C7 H7A . . 110.4
C8 C7 H7A . . 110.4
O1 C7 H7B . . 110.4
C8 C7 H7B . . 110.4
H7A C7 H7B . . 108.6
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
O2 C9 C11 . . 107.84(16)
O2 C9 C10 . . 107.22(17)
C11 C9 C10 . . 113.9(2)
O2 C9 H9 . . 109.3
C11 C9 H9 . . 109.3
C10 C9 H9 . . 109.3
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C9 C11 H11A . . 109.5
C9 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C9 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S2 . 2.2328(5)
Ni1 S2 2_665 2.2328(5)
Ni1 S1 2_665 2.2369(5)
Ni1 S1 . 2.2369(5)
Ni1 P1 . 2.8224(5)
Ni1 P1 2_665 2.8224(5)
S1 P1 . 2.0035(7)
S2 P1 . 2.0053(7)
P1 O2 . 1.5828(12)
P1 C1 . 1.7894(18)
O1 C4 . 1.364(2)
O1 C7 . 1.438(3)
O2 C9 . 1.484(2)
C1 C6 . 1.385(3)
C1 C2 . 1.386(3)
C2 C3 . 1.383(3)
C2 H2 . 0.9500
C3 C4 . 1.381(3)
C3 H3 . 0.9500
C4 C5 . 1.387(3)
C5 C6 . 1.378(3)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 C8 . 1.513(3)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 C11 . 1.489(3)
C9 C10 . 1.497(3)
C9 H9 . 1.0000
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
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_site_symmetry_1
_geom_torsion
S2 Ni1 S1 P1 . 12.58(2)
S2 Ni1 S1 P1 2_665 -167.42(2)
P1 Ni1 S1 P1 2_665 180.0
S1 Ni1 S2 P1 2_665 167.43(2)
S1 Ni1 S2 P1 . -12.57(2)
P1 Ni1 S2 P1 2_665 180.0
Ni1 S1 P1 O2 . -137.71(6)
Ni1 S1 P1 C1 . 107.99(7)
Ni1 S1 P1 S2 . -14.35(3)
Ni1 S2 P1 O2 . 137.47(6)
Ni1 S2 P1 C1 . -107.90(7)
Ni1 S2 P1 S1 . 14.37(3)
S2 Ni1 P1 O2 . -81.30(9)
S2 Ni1 P1 O2 2_665 98.70(9)
S1 Ni1 P1 O2 2_665 -99.27(9)
S1 Ni1 P1 O2 . 80.73(9)
S2 Ni1 P1 C1 . 99.02(8)
S2 Ni1 P1 C1 2_665 -80.98(8)
S1 Ni1 P1 C1 2_665 81.05(8)
S1 Ni1 P1 C1 . -98.95(8)
S2 Ni1 P1 S1 . -162.03(3)
S2 Ni1 P1 S1 2_665 17.97(3)
S1 Ni1 P1 S1 2_665 180.0000(10)
S2 Ni1 P1 S2 2_665 180.0
S1 Ni1 P1 S2 2_665 -17.97(3)
S1 Ni1 P1 S2 . 162.03(3)
C1 P1 O2 C9 . -179.91(14)
S1 P1 O2 C9 . 58.46(15)
S2 P1 O2 C9 . -57.97(15)
Ni1 P1 O2 C9 . 0.38(19)
O2 P1 C1 C6 . 101.89(17)
S1 P1 C1 C6 . -136.21(15)
S2 P1 C1 C6 . -20.53(18)
Ni1 P1 C1 C6 . -78.31(17)
O2 P1 C1 C2 . -75.50(16)
S1 P1 C1 C2 . 46.41(17)
S2 P1 C1 C2 . 162.08(14)
Ni1 P1 C1 C2 . 104.30(15)
C6 C1 C2 C3 . -2.3(3)
P1 C1 C2 C3 . 175.20(15)
C1 C2 C3 C4 . 0.4(3)
C7 O1 C4 C3 . 10.4(3)
C7 O1 C4 C5 . -169.75(19)
C2 C3 C4 O1 . -178.27(18)
C2 C3 C4 C5 . 1.9(3)
O1 C4 C5 C6 . 177.9(2)
C3 C4 C5 C6 . -2.2(3)
C4 C5 C6 C1 . 0.3(3)
C2 C1 C6 C5 . 1.9(3)
P1 C1 C6 C5 . -175.49(17)
C4 O1 C7 C8 . 169.83(18)
P1 O2 C9 C11 . 112.06(18)
P1 O2 C9 C10 . -124.87(18)
