#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201956.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_2201956
loop_
_publ_author_name
'Laifa El Adoui'
'Nourredine Benali-Cherif'
'Hocine Merazig'
_publ_section_title
Undecacarbonyl(μ₄-2-thiodithiobenzoato-κ⁴C,S,S',S'')(trimethylphosphite)tetrafer
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m108
_journal_page_last               m110
_journal_paper_doi               10.1107/S1600536803003052
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Fe4 (C3 H9 O3 P1) (C7 H4 S3) (C O)11]'
_chemical_formula_moiety         'C21 H13 Fe4 O14 P1 S3'
_chemical_formula_structural     'FE4 S3 P C21 O14 H13'
_chemical_formula_sum            'C21 H13 Fe4 O14 P S3'
_chemical_formula_weight         839.89
_chemical_melting_point          210
_chemical_name_common
;
Undecacarbonyl(μ₄-2-thiodithiobenzoato-
κ⁴C,S,S',S'')(trimethylphosphite)tetrafer
;
_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
_cell_angle_alpha                93.971(2)
_cell_angle_beta                 100.923(5)
_cell_angle_gamma                111.959(5)
_cell_formula_units_Z            2
_cell_length_a                   9.263(5)
_cell_length_b                   11.588(5)
_cell_length_c                   15.784(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1524.5(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6499
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0.01
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.474
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6179
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0601P)²+0.2274P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                4937
_reflns_number_total             6179
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6051.cif
_cod_data_source_block           I
_cod_original_cell_volume        1524.5(12)
_cod_original_formula_sum        'C21 H13 Fe4 O14 P1 S3'
_cod_database_code               2201956
_cod_database_fobs_code          2201956
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
C1 0.0641(3) 0.2051(2) 0.66065(17) 0.0383(5) Uani d . 1 . . C
C2 -0.0901(3) 0.1117(2) 0.66930(19) 0.0428(6) Uani d . 1 . . C
C3 -0.1294(3) 0.0898(3) 0.7496(2) 0.0512(7) Uani d . 1 . . C
C4 -0.2748(4) -0.0065(4) 0.7522(3) 0.0759(11) Uani d . 1 . . C
H4 -0.3003 -0.0216 0.8057 0.091 Uiso calc R 1 . . H
C5 -0.3800(5) -0.0788(4) 0.6768(4) 0.0892(13) Uani d . 1 . . C
H5 -0.4761 -0.1425 0.6794 0.107 Uiso calc R 1 . . H
C6 -0.3435(4) -0.0572(3) 0.5980(3) 0.0760(11) Uani d . 1 . . C
H6 -0.4153 -0.1061 0.5469 0.091 Uiso calc R 1 . . H
C7 -0.2016(4) 0.0362(3) 0.5936(2) 0.0557(7) Uani d . 1 . . C
H7 -0.1788 0.0497 0.5394 0.067 Uiso calc R 1 . . H
C8 0.1430(7) 0.3957(4) 0.9694(3) 0.0947(14) Uani d . 1 . . C
C9 0.3416(6) 0.5045(4) 0.8814(3) 0.0859(12) Uani d . 1 . . C
C10 0.0195(5) 0.4321(4) 0.8073(3) 0.0735(10) Uani d . 1 . . C
C11 0.2544(6) 0.1568(4) 0.9776(3) 0.0807(11) Uani d . 1 . . C
C12 0.4604(5) 0.2557(4) 0.8920(2) 0.0713(10) Uani d . 1 . . C
C13 0.1416(4) 0.3878(3) 0.4746(2) 0.0542(7) Uani d . 1 . . C
C14 0.1641(4) 0.4870(3) 0.6377(2) 0.0549(7) Uani d . 1 . . C
C15 -0.1105(4) 0.3047(3) 0.5418(2) 0.0531(7) Uani d . 1 . . C
C16 0.4438(3) 0.3574(3) 0.5495(2) 0.0535(7) Uani d . 1 . . C
C17 0.4961(4) 0.4954(3) 0.6966(2) 0.0643(8) Uani d . 1 . . C
C18 0.5146(4) 0.2607(3) 0.6880(3) 0.0657(9) Uani d . 1 . . C
O8 0.1318(6) 0.4116(4) 1.0393(2) 0.1509(19) Uani d . 1 . . O
O9 0.4599(5) 0.5897(4) 0.8980(3) 0.1346(15) Uani d . 1 . . O
O10 -0.0720(4) 0.4701(3) 0.7765(2) 0.1069(11) Uani d . 1 . . O
O11 0.2584(5) 0.1387(4) 1.04755(19) 0.1217(13) Uani d . 1 . . O
O12 0.5960(4) 0.3008(3) 0.9091(2) 0.1121(11) Uani d . 1 . . O
O13 0.1647(3) 0.4173(3) 0.40977(17) 0.0802(7) Uani d . 1 . . O
O14 0.2080(3) 0.5874(2) 0.67283(18) 0.0813(8) Uani d . 1 . . O
O15 -0.2423(3) 0.2867(3) 0.5220(2) 0.0845(8) Uani d . 1 . . O
O16 0.4830(3) 0.3680(2) 0.48578(17) 0.0673(6) Uani d . 1 . . O
O17 0.5716(4) 0.5968(3) 0.7258(2) 0.1028(10) Uani d . 1 . . O
O18 0.6026(4) 0.2169(3) 0.7097(3) 0.1068(11) Uani d . 1 . . O
S1 -0.00663(11) 0.16723(8) 0.85468(5) 0.0587(2) Uani d . 1 . . S
S2 0.22733(8) 0.28083(6) 0.75232(4) 0.04077(15) Uani d . 1 . . S
S3 0.15241(8) 0.16762(6) 0.57733(4) 0.04108(15) Uani d . 1 . . S
Fe1 0.15957(6) 0.36938(4) 0.85957(3) 0.05849(14) Uani d . 1 . . Fe
Fe3 0.09722(4) 0.33472(3) 0.57491(2) 0.03976(11) Uani d . 1 . . Fe
Fe4 0.37651(4) 0.33337(3) 0.64835(3) 0.04323(11) Uani d . 1 . . Fe
Fe2 0.24825(6) 0.18620(4) 0.86845(3) 0.05237(12) Uani d D 1 A . Fe
P1 0.21962(10) 0.00023(7) 0.81367(6) 0.0562(2) Uani d D 1 . . P
O19 0.2791(7) -0.0021(6) 0.7252(4) 0.0728(17) Uani d PDU 0.58 A 1 O
C19 0.213(2) -0.1009(12) 0.6531(11) 0.1034(17) Uani d PDU 0.58 A 1 C
H19A 0.1887 -0.1804 0.6739 0.155 Uiso calc PR 0.58 A 1 H
H19B 0.2890 -0.0907 0.6175 0.155 Uiso calc PR 0.58 A 1 H
H19C 0.1170 -0.0985 0.6191 0.155 Uiso calc PR 0.58 A 1 H
O20 0.3269(13) -0.0539(8) 0.8740(5) 0.087(2) Uani d PDU 0.58 A 1 O
C20 0.3423(11) -0.1701(7) 0.8593(6) 0.1034(17) Uani d PDU 0.58 A 1 C
H20A 0.2381 -0.2366 0.8390 0.155 Uiso calc PR 0.58 A 1 H
H20B 0.3958 -0.1858 0.9129 0.155 Uiso calc PR 0.58 A 1 H
H20C 0.4037 -0.1669 0.8162 0.155 Uiso calc PR 0.58 A 1 H
O21 0.0550(7) -0.1126(5) 0.7790(5) 0.100(2) Uani d PDU 0.58 A 1 O
C21 -0.0306(12) -0.1630(9) 0.8435(6) 0.1034(17) Uani d PDU 0.58 A 1 C
H21A -0.0008 -0.0984 0.8927 0.155 Uiso calc PR 0.58 A 1 H
H21B -0.0048 -0.2315 0.8622 0.155 Uiso calc PR 0.58 A 1 H
H21C -0.1436 -0.1929 0.8190 0.155 Uiso calc PR 0.58 A 1 H
O19A 0.1918(11) -0.0148(9) 0.7152(5) 0.078(3) Uani d PDU 0.42 A 2 O
C19A 0.192(4) -0.111(2) 0.6550(15) 0.145(4) Uani d PDU 0.42 A 2 C
H19D 0.2522 -0.0737 0.6136 0.217 Uiso calc PR 0.42 A 2 H
H19E 0.0838 -0.1631 0.6248 0.217 Uiso calc PR 0.42 A 2 H
H19F 0.2398 -0.1611 0.6857 0.217 Uiso calc PR 0.42 A 2 H
O20A 0.3526(17) -0.0441(13) 0.8426(8) 0.106(5) Uani d PDU 0.42 A 2 O
C20A 0.387(2) -0.0726(14) 0.9265(7) 0.145(4) Uani d PD 0.42 A 2 C
H20D 0.4233 0.0023 0.9684 0.217 Uiso calc PR 0.42 A 2 H
H20E 0.4690 -0.1051 0.9313 0.217 Uiso calc PR 0.42 A 2 H
H20F 0.2922 -0.1346 0.9375 0.217 Uiso calc PR 0.42 A 2 H
O21A 0.0669(14) -0.0978(8) 0.8376(8) 0.135(5) Uani d PDU 0.42 A 2 O
C21A -0.042(2) -0.2224(11) 0.7950(9) 0.145(4) Uani d PDU 0.42 A 2 C
H21D 0.0165 -0.2650 0.7716 0.217 Uiso calc PR 0.42 A 2 H
H21E -0.1209 -0.2165 0.7484 0.217 Uiso calc PR 0.42 A 2 H
H21F -0.0936 -0.2687 0.8364 0.217 Uiso calc PR 0.42 A 2 H
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -3 7
-1 5 4
8 -3 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 S2 121.8(2) ?
C2 C1 S3 118.41(18) ?
S2 C1 S3 104.52(14) ?
C2 C1 Fe3 126.52(18) ?
S2 C1 Fe3 104.06(12) ?
S3 C1 Fe3 68.51(9) ?
C3 C2 C7 117.6(3) ?
C3 C2 C1 123.5(3) ?
C7 C2 C1 118.8(3) ?
C2 C3 C4 119.7(3) ?
C2 C3 S1 126.6(2) ?
C4 C3 S1 113.6(3) ?
C5 C4 C3 120.9(4) ?
C6 C5 C4 119.9(3) ?
C5 C6 C7 120.4(4) ?
C6 C7 C2 121.4(3) ?
O8 C8 Fe1 179.5(5) ?
O9 C9 Fe1 177.6(4) ?
O10 C10 Fe1 177.5(4) ?
O11 C11 Fe2 179.6(4) ?
O12 C12 Fe2 178.4(4) ?
O13 C13 Fe3 177.4(3) ?
O14 C14 Fe3 175.5(3) ?
O15 C15 Fe3 178.9(3) ?
O16 C16 Fe4 177.4(3) ?
O17 C17 Fe4 179.1(4) ?
O18 C18 Fe4 177.2(4) ?
C3 S1 Fe2 112.41(10) ?
C3 S1 Fe1 114.95(10) ?
Fe2 S1 Fe1 68.83(4) ?
C1 S2 Fe2 119.91(9) ?
C1 S2 Fe1 112.42(9) ?
Fe2 S2 Fe1 70.09(3) ?
C1 S2 Fe4 84.14(9) ?
Fe2 S2 Fe4 133.26(4) ?
Fe1 S2 Fe4 141.04(4) ?
C1 S3 Fe3 61.92(8) ?
C1 S3 Fe4 85.59(9) ?
Fe3 S3 Fe4 72.77(4) ?
C9 Fe1 C8 90.4(2) ?
C9 Fe1 C10 101.0(2) ?
C8 Fe1 C10 98.7(2) ?
C9 Fe1 S2 92.10(14) ?
C8 Fe1 S2 154.02(15) ?
C10 Fe1 S2 106.18(12) ?
C9 Fe1 S1 158.42(15) ?
C8 Fe1 S1 86.94(15) ?
C10 Fe1 S1 100.56(14) ?
S2 Fe1 S1 81.27(4) ?
C9 Fe1 Fe2 104.03(16) ?
C8 Fe1 Fe2 99.63(15) ?
C10 Fe1 Fe2 148.69(13) ?
S2 Fe1 Fe2 54.73(2) ?
S1 Fe1 Fe2 55.52(4) ?
C14 Fe3 C15 98.35(14) ?
C14 Fe3 C13 96.84(14) ?
C15 Fe3 C13 94.16(14) ?
C14 Fe3 C1 107.53(12) ?
C15 Fe3 C1 94.26(12) ?
C13 Fe3 C1 152.71(12) ?
C14 Fe3 S3 138.67(10) ?
C15 Fe3 S3 115.25(10) ?
C13 Fe3 S3 103.60(10) ?
C1 Fe3 S3 49.57(7) ?
C14 Fe3 Fe4 86.86(10) ?
C15 Fe3 Fe4 165.22(10) ?
C13 Fe3 Fe4 98.96(10) ?
C1 Fe3 Fe4 70.96(7) ?
S3 Fe3 Fe4 54.95(2) ?
C16 Fe4 C17 91.80(15) ?
C16 Fe4 C18 92.67(15) ?
C17 Fe4 C18 100.35(17) ?
C16 Fe4 S3 91.18(10) ?
C17 Fe4 S3 156.07(12) ?
C18 Fe4 S3 103.22(13) ?
C16 Fe4 S2 165.66(10) ?
C17 Fe4 S2 97.27(12) ?
C18 Fe4 S2 96.58(12) ?
S3 Fe4 S2 76.07(4) ?
C16 Fe4 Fe3 91.66(10) ?
C17 Fe4 Fe3 103.89(12) ?
C18 Fe4 Fe3 155.21(12) ?
S3 Fe4 Fe3 52.28(3) ?
S2 Fe4 Fe3 75.42(4) ?
C11 Fe2 C12 90.37(19) ?
C11 Fe2 P1 96.36(14) ?
C12 Fe2 P1 97.05(13) ?
C11 Fe2 S2 159.64(14) ?
C12 Fe2 S2 92.28(12) ?
P1 Fe2 S2 103.33(4) y
C11 Fe2 S1 89.10(15) ?
C12 Fe2 S1 160.09(13) ?
P1 Fe2 S1 102.78(4) y
S2 Fe2 S1 81.62(3) y
C11 Fe2 Fe1 104.72(14) ?
C12 Fe2 Fe1 105.45(13) ?
P1 Fe2 Fe1 148.78(4) y
S2 Fe2 Fe1 55.18(2) y
S1 Fe2 Fe1 55.65(3) y
O20A P1 O19A 104.5(6) ?
O20A P1 O21 111.6(7) ?
O19A P1 O21 74.7(5) ?
O20A P1 O20 21.9(6) ?
O19A P1 O20 124.2(4) ?
O21 P1 O20 105.3(5) ?
O20A P1 O21A 105.8(7) ?
O19A P1 O21A 108.1(6) ?
O21 P1 O21A 33.5(4) ?
O20 P1 O21A 89.2(7) ?
O20A P1 O19 80.4(5) ?
O19A P1 O19 27.7(3) ?
O21 P1 O19 96.0(4) ?
O20 P1 O19 102.0(4) ?
O21A P1 O19 128.7(5) ?
O20A P1 Fe2 119.1(6) ?
O19A P1 Fe2 111.5(3) ?
O21 P1 Fe2 124.2(3) ?
O20 P1 Fe2 112.8(3) ?
O21A P1 Fe2 107.4(4) ?
O19 P1 Fe2 113.3(3) ?
C19 O19 P1 126.8(8) ?
C20 O20 P1 128.8(7) ?
C21 O21 P1 116.0(7) ?
C19A O19A P1 130.4(13) ?
C20A O20A P1 121.5(12) ?
C21A O21A P1 131.2(11) ?
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
C1 C2 . 1.472(4) y
C1 S2 . 1.775(3) y
C1 S3 . 1.784(3) y
C1 Fe3 . 2.068(3) y
C2 C3 . 1.398(4) ?
C2 C7 . 1.404(4) ?
C3 C4 . 1.401(4) ?
C3 S1 . 1.779(3) y
C4 C5 . 1.370(6) ?
C5 C6 . 1.365(6) ?
C6 C7 . 1.373(5) ?
C8 O8 . 1.136(5) ?
C8 Fe1 . 1.785(4) ?
C9 O9 . 1.136(5) ?
C9 Fe1 . 1.773(5) ?
C10 O10 . 1.141(5) ?
C10 Fe1 . 1.809(4) ?
C11 O11 . 1.135(5) ?
C11 Fe2 . 1.773(4) ?
C12 O12 . 1.133(5) ?
C12 Fe2 . 1.774(4) ?
C13 O13 . 1.135(4) ?
C13 Fe3 . 1.801(3) ?
C14 O14 . 1.140(4) ?
C14 Fe3 . 1.785(3) ?
C15 O15 . 1.135(4) ?
C15 Fe3 . 1.786(3) ?
C16 O16 . 1.131(4) ?
C16 Fe4 . 1.789(3) ?
C17 O17 . 1.127(4) ?
C17 Fe4 . 1.806(4) ?
C18 O18 . 1.126(4) ?
C18 Fe4 . 1.820(4) ?
S1 Fe2 . 2.2540(16) y
S1 Fe1 . 2.2575(13) y
S2 Fe2 . 2.2142(8) y
S2 Fe1 . 2.2264(9) y
S2 Fe4 . 2.3112(9) y
S3 Fe3 . 2.1807(11) y
S3 Fe4 . 2.2567(10) y
Fe1 Fe2 . 2.5499(11) y
Fe3 Fe4 . 2.6331(14) y
Fe2 P1 . 2.1655(13) y
P1 O20A . 1.511(9) ?
P1 O19A . 1.513(8) ?
P1 O21 . 1.558(6) ?
P1 O20 . 1.575(7) ?
P1 O21A . 1.579(8) ?
P1 O19 . 1.597(6) ?
O19 C19 . 1.419(13) ?
O20 C20 . 1.415(9) ?
O21 C21 . 1.431(9) ?
O19A C19A . 1.414(16) ?
O20A C20A . 1.393(10) ?
O21A C21A . 1.439(11) ?
