#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/34/2223414.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_2223414
loop_
_publ_author_name
'Djedouani, Amel'
'Boufas, Sihem'
'Bendaas, Abderrahmen'
'Allain, Magali'
'Bouet, Gilles'
_publ_section_title
;
 Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis(dimethyl
 sulfoxide)nickel(II)
;
_journal_coeditor_code           HG2559
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1205
_journal_page_last               m1206
_journal_paper_doi               10.1107/S1600536809034655
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C8 H7 O4)2 (C2 H6 O S)2]'
_chemical_formula_moiety         'C20 H26 Ni O10 S2'
_chemical_formula_sum            'C20 H26 Ni O10 S2'
_chemical_formula_weight         549.24
_chemical_name_systematic
;
Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis(dimethyl
sulfoxide)nickel(II)
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 123.525(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3850(10)
_cell_length_b                   6.2833(4)
_cell_length_c                   19.7434(15)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.82
_cell_volume                     1177.40(18)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'DIAMOND (Brandenburg, 1998) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14084
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_T_max  0.9019
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.973
_refine_ls_extinction_coef       0.0084(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²+0.3428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                1962
_reflns_number_total             2628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2559.cif
_cod_data_source_block           I
_cod_original_cell_volume        1177.40(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223414
_cod_database_fobs_code          2223414
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_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_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.5 0.5 0.5 0.02521(16) Uani d S 1 . .
S S1 0.75777(6) 0.76611(10) 0.53190(4) 0.03283(19) Uani d . 1 . .
O O5 0.22643(18) 0.1935(3) 0.18093(9) 0.0384(4) Uani d . 1 . .
O O1 0.62169(17) 0.6626(3) 0.46467(10) 0.0387(4) Uani d . 1 . .
O O2 0.47029(16) 0.2626(3) 0.42577(9) 0.0307(4) Uani d . 1 . .
O O3 0.32165(16) 0.6292(3) 0.40600(9) 0.0316(4) Uani d . 1 . .
O O4 0.1020(2) 0.4798(3) 0.15900(11) 0.0478(5) Uani d . 1 . .
C C6 0.2779(2) 0.4022(4) 0.29848(13) 0.0252(5) Uani d . 1 . .
C C3 0.1192(3) 0.7190(4) 0.28219(15) 0.0378(6) Uani d . 1 . .
H H3A 0.1101 0.8133 0.3173 0.057 Uiso calc R 1 . .
H H3B 0.0368 0.631 0.2527 0.057 Uiso calc R 1 . .
H H3C 0.1291 0.801 0.2446 0.057 Uiso calc R 1 . .
C C10 0.3256(3) 0.0457(4) 0.23083(15) 0.0317(6) Uani d . 1 . .
C C8 0.3859(2) 0.2500(4) 0.34964(14) 0.0253(5) Uani d . 1 . .
C C9 0.3994(2) 0.0651(4) 0.31075(14) 0.0296(5) Uani d . 1 . .
H H9 0.4616 -0.0426 0.3428 0.036 Uiso calc R 1 . .
C C5 0.2474(2) 0.5807(4) 0.33237(13) 0.0265(5) Uani d . 1 . .
C C2 0.7743(3) 1.0036(4) 0.48915(18) 0.0469(7) Uani d . 1 . .
H H2A 0.7626 0.9718 0.4382 0.07 Uiso calc R 1 . .
H H2B 0.8659 1.0642 0.5256 0.07 Uiso calc R 1 . .
H H2C 0.7034 1.1033 0.4805 0.07 Uiso calc R 1 . .
C C7 0.1958(2) 0.3697(4) 0.21184(14) 0.0312(6) Uani d . 1 . .
C C4 0.3357(3) -0.1273(5) 0.18287(17) 0.0470(7) Uani d . 1 . .
H H4A 0.4053 -0.2289 0.2191 0.071 Uiso calc R 1 . .
H H4B 0.3623 -0.0679 0.1484 0.071 Uiso calc R 1 . .
H H4C 0.246 -0.1966 0.1501 0.071 Uiso calc R 1 . .
C C1 0.8954(3) 0.6199(5) 0.53594(19) 0.0526(8) Uani d . 1 . .
H H1A 0.8972 0.4776 0.5542 0.079 Uiso calc R 1 . .
H H1B 0.9841 0.6879 0.573 0.079 Uiso calc R 1 . .
H H1C 0.8792 0.6154 0.4828 0.079 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_publ_flag
O2 Ni1 O2 3_666 . 180 ?
O2 Ni1 O3 3_666 . 92.94(6) ?
O2 Ni1 O3 . . 87.06(6) ?
O2 Ni1 O3 3_666 3_666 87.06(6) ?
O2 Ni1 O3 . 3_666 92.94(6) ?
O3 Ni1 O3 . 3_666 180.0000(10) ?
O2 Ni1 O1 3_666 3_666 89.72(7) ?
O2 Ni1 O1 . 3_666 90.28(7) ?
O3 Ni1 O1 . 3_666 89.31(7) ?
O3 Ni1 O1 3_666 3_666 90.69(7) ?
O2 Ni1 O1 3_666 . 90.28(7) ?
O2 Ni1 O1 . . 89.72(7) ?
O3 Ni1 O1 . . 90.69(7) ?
O3 Ni1 O1 3_666 . 89.31(7) ?
O1 Ni1 O1 3_666 . 180 ?
O1 S1 C2 . . 105.60(12) ?
O1 S1 C1 . . 105.41(12) ?
C2 S1 C1 . . 97.65(15) ?
C10 O5 C7 . . 121.85(18) ?
S1 O1 Ni1 . . 116.97(9) ?
C8 O2 Ni1 . . 129.32(15) ?
C5 O3 Ni1 . . 131.49(15) ?
C8 C6 C7 . . 118.8(2) ?
C8 C6 C5 . . 121.45(19) ?
C7 C6 C5 . . 119.74(19) ?
C5 C3 H3A . . 109.5 ?
C5 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C5 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C9 C10 O5 . . 121.6(2) ?
C9 C10 C4 . . 127.3(2) ?
O5 C10 C4 . . 111.1(2) ?
O2 C8 C6 . . 125.9(2) ?
O2 C8 C9 . . 116.6(2) ?
C6 C8 C9 . . 117.4(2) ?
C10 C9 C8 . . 121.6(2) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
O3 C5 C6 . . 123.2(2) ?
O3 C5 C3 . . 114.3(2) ?
C6 C5 C3 . . 122.51(19) ?
S1 C2 H2A . . 109.5 ?
S1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
S1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
O4 C7 O5 . . 112.9(2) ?
O4 C7 C6 . . 128.7(2) ?
O5 C7 C6 . . 118.4(2) ?
C10 C4 H4A . . 109.5 ?
C10 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C10 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
S1 C1 H1A . . 109.5 ?
S1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
S1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 O2 3_666 1.9849(16) yes
Ni1 O2 . 1.9849(16) yes
Ni1 O3 . 2.0159(15) yes
Ni1 O3 3_666 2.0159(15) yes
Ni1 O1 3_666 2.1255(18) yes
Ni1 O1 . 2.1255(18) yes
S1 O1 . 1.5211(17) ?
S1 C2 . 1.775(3) ?
S1 C1 . 1.780(3) ?
O5 C10 . 1.371(3) ?
O5 C7 . 1.398(3) ?
O2 C8 . 1.262(3) ?
O3 C5 . 1.250(3) ?
O4 C7 . 1.215(3) ?
C6 C8 . 1.440(3) ?
C6 C7 . 1.441(3) ?
C6 C5 . 1.443(3) ?
C3 C5 . 1.507(3) ?
C3 H3A . 0.96 ?
C3 H3B . 0.96 ?
C3 H3C . 0.96 ?
C10 C9 . 1.321(3) ?
C10 C4 . 1.487(4) ?
C8 C9 . 1.447(3) ?
C9 H9 . 0.93 ?
C2 H2A . 0.96 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1B O4 4_676 0.9600 2.5500 3.384(4) 145.00 yes
C2 H2B O4 4_676 0.9600 2.5300 3.370(4) 146.00 yes
C2 H2C O2 1_565 0.9600 2.4600 3.378(4) 160.00 yes
