#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:01:48 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179436 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/33/4333379.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4333379
loop_
_publ_author_name
'Hu, Chuanjiang'
'Noll, Bruce C.'
'Scheidt, W. Robert'
_publ_section_title
;
 Sulfoxide as a Ligand in Iron(II) Porphyrinates:  S- or O-Bound?
;
_journal_issue                   20
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8258
_journal_page_last               8263
_journal_paper_doi               10.1021/ic7008495
_journal_volume                  46
_journal_year                    2007
_chemical_formula_moiety         'C52 H44 Fe N4 O2 S2'
_chemical_formula_sum            'C52 H44 Fe N4 O2 S2'
_chemical_formula_weight         876.88
_chemical_melting_point          ?
_chemical_name_common            Fe(TPP)(TMSO)2
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.2460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.2580(3)
_cell_length_b                   15.9262(5)
_cell_length_c                   12.3930(4)
_cell_measurement_reflns_used    8883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3196
_cell_measurement_theta_min      2.2344
_cell_volume                     1992.95(11)
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_collection       'BRUKER APEX2'
_computing_data_reduction        'BRUKER SAINT/XPREP'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'φ 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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24711
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9021
_exptl_absorpt_correction_T_min  0.8248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0275
_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)+(0.0461P)²+1.4430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                3846
_reflns_number_total             4085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7008495sup1.cif
_cod_data_source_block           final
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Monoclinic' changed to 'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1992.95(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4333379
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_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
Fe1 Fe 0.5000 0.0000 0.0000 0.00873(9) Uani 1 2 d S
N1 N 0.64838(11) 0.04229(7) 0.15194(10) 0.0103(2) Uani 1 1 d .
N2 N 0.52162(11) 0.09752(7) -0.09088(10) 0.0103(2) Uani 1 1 d .
C(A1 C 0.68820(14) 0.01182(9) 0.26711(12) 0.0110(3) Uani 1 1 d .
C(A2 C 0.71584(13) 0.11697(8) 0.16630(12) 0.0109(3) Uani 1 1 d .
C(A3 C 0.60615(14) 0.16498(8) -0.04404(12) 0.0112(3) Uani 1 1 d .
C(A4 C 0.45395(14) 0.11317(9) -0.21263(12) 0.0113(3) Uani 1 1 d .
C(B1 C 0.78282(14) 0.06801(9) 0.35371(12) 0.0132(3) Uani 1 1 d .
H(B1 H 0.8245 0.0612 0.4386 0.016 Uiso 1 1 calc R
C(B2 C 0.80100(14) 0.13206(9) 0.29160(12) 0.0131(3) Uani 1 1 d .
H(B2 H 0.8591 0.1784 0.3243 0.016 Uiso 1 1 calc R
C(B3 C 0.58709(14) 0.22496(9) -0.13731(13) 0.0135(3) Uani 1 1 d .
H(B3 H 0.6320 0.2770 -0.1277 0.016 Uiso 1 1 calc R
C(B4 C 0.49344(14) 0.19329(9) -0.24079(13) 0.0135(3) Uani 1 1 d .
H(B4 H 0.4597 0.2189 -0.3179 0.016 Uiso 1 1 calc R
C(M1 C 0.69896(14) 0.17383(9) 0.07522(12) 0.0111(3) Uani 1 1 d .
C(M2 C 0.35959(14) 0.06055(9) -0.29752(12) 0.0109(3) Uani 1 1 d .
C11 C 0.78775(14) 0.24923(9) 0.10846(12) 0.0115(3) Uani 1 1 d .
C12 C 0.74883(15) 0.32495(9) 0.13864(13) 0.0162(3) Uani 1 1 d .
H12 H 0.6649 0.3290 0.1392 0.019 Uiso 1 1 calc R
C13 C 0.83132(16) 0.39485(9) 0.16802(14) 0.0184(3) Uani 1 1 d .
H13 H 0.8029 0.4465 0.1871 0.022 Uiso 1 1 calc R
C14 C 0.95506(15) 0.38922(9) 0.16950(13) 0.0172(3) Uani 1 1 d .
H14 H 1.0116 0.4369 0.1896 0.021 Uiso 1 1 calc R
C15 C 0.99563(15) 0.31360(10) 0.14138(13) 0.0175(3) Uani 1 1 d .
H15 H 1.0808 0.3092 0.1436 0.021 Uiso 1 1 calc R
C16 C 0.91212(14) 0.24419(9) 0.11000(13) 0.0153(3) Uani 1 1 d .
H16 H 0.9401 0.1929 0.0894 0.018 Uiso 1 1 calc R
C21 C 0.31678(14) 0.08093(8) -0.42761(12) 0.0116(3) Uani 1 1 d .
C22 C 0.18598(15) 0.09841(9) -0.50856(13) 0.0144(3) Uani 1 1 d .
H22 H 0.1181 0.0949 -0.4830 0.017 Uiso 1 1 calc R
C23 C 0.15452(16) 0.12100(9) -0.62674(13) 0.0172(3) Uani 1 1 d .
H23 H 0.0653 0.1334 -0.6810 0.021 Uiso 1 1 calc R
C24 C 0.25235(16) 0.12556(9) -0.66582(13) 0.0175(3) Uani 1 1 d .
H24 H 0.2306 0.1424 -0.7459 0.021 Uiso 1 1 calc R
C25 C 0.38190(16) 0.10544(9) -0.58751(13) 0.0172(3) Uani 1 1 d .
H25 H 0.4489 0.1071 -0.6143 0.021 Uiso 1 1 calc R
C26 C 0.41348(15) 0.08282(9) -0.46969(13) 0.0143(3) Uani 1 1 d .
H26 H 0.5023 0.0684 -0.4167 0.017 Uiso 1 1 calc R
S1 S 0.36302(3) 0.07402(2) 0.04813(3) 0.01066(9) Uani 1 1 d .
O1 O 0.41639(11) 0.11685(7) 0.16616(9) 0.0210(2) Uani 1 1 d .
C1 C 0.21772(16) 0.01706(10) 0.03337(16) 0.0207(3) Uani 1 1 d .
H1A H 0.1966 -0.0283 -0.0270 0.025 Uiso 1 1 calc R
H1B H 0.2332 -0.0085 0.1113 0.025 Uiso 1 1 calc R
C2 C 0.10316(15) 0.08035(10) -0.00682(14) 0.0186(3) Uani 1 1 d .
H2A H 0.0720 0.0854 0.0561 0.022 Uiso 1 1 calc R
H2B H 0.0283 0.0603 -0.0816 0.022 Uiso 1 1 calc R
C3 C 0.15021(15) 0.16667(10) -0.02904(14) 0.0179(3) Uani 1 1 d .
H3A H 0.0769 0.1963 -0.0954 0.021 Uiso 1 1 calc R
H3B H 0.1811 0.2017 0.0443 0.021 Uiso 1 1 calc R
C4 C 0.26375(15) 0.15010(9) -0.06210(13) 0.0155(3) Uani 1 1 d .
H4A H 0.3147 0.2020 -0.0561 0.019 Uiso 1 1 calc R
H4B H 0.2305 0.1272 -0.1446 0.019 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'
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Fe1 N2 180.0 . 3_655
N2 Fe1 N1 90.55(5) . .
N2 Fe1 N1 89.44(5) 3_655 .
N2 Fe1 N1 89.45(5) . 3_655
N2 Fe1 N1 90.56(5) 3_655 3_655
N1 Fe1 N1 180.0 . 3_655
N2 Fe1 S1 90.63(3) . .
N2 Fe1 S1 89.37(3) 3_655 .
N1 Fe1 S1 87.62(3) . .
N1 Fe1 S1 92.38(3) 3_655 .
N2 Fe1 S1 89.37(3) . 3_655
N2 Fe1 S1 90.63(3) 3_655 3_655
N1 Fe1 S1 92.38(3) . 3_655
N1 Fe1 S1 87.62(3) 3_655 3_655
S1 Fe1 S1 180.0 . 3_655
C(A2 N1 C(A1 105.13(11) . .
C(A2 N1 Fe1 126.45(9) . .
C(A1 N1 Fe1 127.46(9) . .
C(A4 N2 C(A3 105.29(11) . .
C(A4 N2 Fe1 127.72(9) . .
C(A3 N2 Fe1 126.97(9) . .
N1 C(A1 C(M2 125.65(13) . 3_655
N1 C(A1 C(B1 110.28(12) . .
C(M2 C(A1 C(B1 124.01(13) 3_655 .
N1 C(A2 C(M1 125.87(13) . .
N1 C(A2 C(B2 110.43(12) . .
C(M1 C(A2 C(B2 123.56(13) . .
N2 C(A3 C(M1 125.46(12) . .
N2 C(A3 C(B3 110.37(12) . .
C(M1 C(A3 C(B3 124.15(13) . .
N2 C(A4 C(M2 125.73(12) . .
N2 C(A4 C(B4 110.12(12) . .
C(M2 C(A4 C(B4 124.15(12) . .
C(B2 C(B1 C(A1 107.09(12) . .
C(B2 C(B1 H(B1 126.5 . .
C(A1 C(B1 H(B1 126.5 . .
C(B1 C(B2 C(A2 107.04(12) . .
C(B1 C(B2 H(B2 126.5 . .
C(A2 C(B2 H(B2 126.5 . .
C(B4 C(B3 C(A3 106.96(12) . .
C(B4 C(B3 H(B3 126.5 . .
C(A3 C(B3 H(B3 126.5 . .
C(B3 C(B4 C(A4 107.21(12) . .
C(B3 C(B4 H(B4 126.4 . .
C(A4 C(B4 H(B4 126.4 . .
C(A3 C(M1 C(A2 124.40(13) . .
C(A3 C(M1 C11 118.04(12) . .
C(A2 C(M1 C11 117.56(12) . .
C(A1 C(M2 C(A4 123.31(12) 3_655 .
C(A1 C(M2 C21 119.41(12) 3_655 .
C(A4 C(M2 C21 117.11(12) . .
C12 C11 C16 118.73(13) . .
C12 C11 C(M1 121.19(12) . .
C16 C11 C(M1 120.09(12) . .
C11 C12 C13 120.75(13) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C14 C13 C12 120.12(14) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C15 C14 C13 119.55(14) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C14 C15 C16 120.26(14) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C15 C16 C11 120.58(13) . .
C15 C16 H16 119.7 . .
C11 C16 H16 119.7 . .
C22 C21 C26 118.38(13) . .
C22 C21 C(M2 123.46(12) . .
C26 C21 C(M2 118.15(13) . .
C23 C22 C21 120.28(13) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C24 C23 C22 120.57(14) . .
C24 C23 H23 119.7 . .
C22 C23 H23 119.7 . .
C25 C24 C23 119.71(13) . .
C25 C24 H24 120.1 . .
C23 C24 H24 120.1 . .
C24 C25 C26 119.81(14) . .
C24 C25 H25 120.1 . .
C26 C25 H25 120.1 . .
C25 C26 C21 121.16(14) . .
C25 C26 H26 119.4 . .
C21 C26 H26 119.4 . .
O1 S1 C4 106.54(7) . .
O1 S1 C1 106.57(7) . .
C4 S1 C1 91.76(7) . .
O1 S1 Fe1 118.91(5) . .
C4 S1 Fe1 115.18(5) . .
C1 S1 Fe1 114.27(5) . .
C2 C1 S1 107.22(10) . .
C2 C1 H1A 110.3 . .
S1 C1 H1A 110.3 . .
C2 C1 H1B 110.3 . .
S1 C1 H1B 110.3 . .
H1A C1 H1B 108.5 . .
C1 C2 C3 109.73(12) . .
C1 C2 H2A 109.7 . .
C3 C2 H2A 109.7 . .
C1 C2 H2B 109.7 . .
C3 C2 H2B 109.7 . .
H2A C2 H2B 108.2 . .
C4 C3 C2 106.75(12) . .
C4 C3 H3A 110.4 . .
C2 C3 H3A 110.4 . .
C4 C3 H3B 110.4 . .
C2 C3 H3B 110.4 . .
H3A C3 H3B 108.6 . .
C3 C4 S1 103.02(9) . .
C3 C4 H4A 111.2 . .
S1 C4 H4A 111.2 . .
C3 C4 H4B 111.2 . .
S1 C4 H4B 111.2 . .
H4A C4 H4B 109.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 N2 1.9956(11) .
Fe1 N2 1.9956(11) 3_655
Fe1 N1 2.0020(11) .
Fe1 N1 2.0020(11) 3_655
Fe1 S1 2.2220(3) .
Fe1 S1 2.2221(3) 3_655
N1 C(A2 1.3797(17) .
N1 C(A1 1.3812(17) .
N2 C(A4 1.3793(17) .
N2 C(A3 1.3814(18) .
C(A1 C(M2 1.3925(19) 3_655
C(A1 C(B1 1.4409(19) .
C(A2 C(M1 1.3929(19) .
C(A2 C(B2 1.4394(19) .
C(A3 C(M1 1.3894(19) .
C(A3 C(B3 1.4405(19) .
C(A4 C(M2 1.396(2) .
C(A4 C(B4 1.4439(19) .
C(B1 C(B2 1.347(2) .
C(B1 H(B1 0.9500 .
C(B2 H(B2 0.9500 .
C(B3 C(B4 1.347(2) .
C(B3 H(B3 0.9500 .
C(B4 H(B4 0.9500 .
C(M1 C11 1.4989(18) .
C(M2 C(A1 1.3926(19) 3_655
C(M2 C21 1.4999(18) .
C11 C12 1.390(2) .
C11 C16 1.394(2) .
C12 C13 1.391(2) .
C12 H12 0.9500 .
C13 C14 1.388(2) .
C13 H13 0.9500 .
C14 C15 1.386(2) .
C14 H14 0.9500 .
C15 C16 1.391(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.395(2) .
C21 C26 1.400(2) .
C22 C23 1.393(2) .
C22 H22 0.9500 .
C23 C24 1.387(2) .
C23 H23 0.9500 .
C24 C25 1.386(2) .
C24 H24 0.9500 .
C25 C26 1.389(2) .
C25 H25 0.9500 .
C26 H26 0.9500 .
S1 O1 1.4794(11) .
S1 C4 1.7981(14) .
S1 C1 1.8076(15) .
C1 C2 1.536(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.541(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.528(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
