#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:52:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179267 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/87/4318796.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_4318796
loop_
_publ_author_name
'Kathleen M. Barkigia'
'Magali Palacio'
'Yu Sun'
'Marc Nogues'
'Mark W. Renner'
'François Varret'
'Pierrette Battioni'
'Daniel Mansuy'
'Jack Fajer'
_publ_contact_author
;
 K.M. Barkigia (regarding the crystallographic data and cif)
 Materials Science Dept.
 Molecular Materials Division
 Bldg. 555
 Brookhaven National Laboratory
 Upton, NY 11973 USA
;
_publ_contact_author_email       barkigia@bnl.gov
_publ_contact_author_fax         631-344-5815
_publ_contact_author_phone       631-344-7661
_publ_section_title
;
 Air-Stable, Electron-Deficient Fe(II) Catalytic Porphyrins.
 Characterization and Molecular Structures of Rare High Spin Fe(II)
 Hexacoordinated Porphyrins
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5647
_journal_page_last               5649
_journal_paper_doi               10.1021/ic025869s
_journal_volume                  41
_journal_year                    2002
_chemical_compound_source        acetone/pentane/ethanol
_chemical_formula_structural
;
 Fe N12 C44 H12 Cl8 O16, 2(C2 H5 OH), (C H2 Cl2)
;
_chemical_formula_sum            'C49 H26 Cl10 Fe N12 O18'
_chemical_formula_weight         1481.17
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL
_cell_angle_alpha                70.51(2)
_cell_angle_beta                 88.85(2)
_cell_angle_gamma                73.60(2)
_cell_formula_units_Z            1
_cell_length_a                   12.001(2)
_cell_length_b                   12.110(4)
_cell_length_c                   12.258(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     1605.7(8)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1977)
_computing_data_collection       CAD4_(Enraf-Nonius,_1977)
_computing_data_reduction        'XCAD4VAX provided with SHELXL-93'
_computing_molecular_graphics    'SHELXTL and other in  house programs'
_computing_publication_material  'CIFTAB provided with SHELXS-86'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Burla et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0941
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4709
_diffrn_reflns_theta_max         58.00
_diffrn_reflns_theta_min         3.84
_diffrn_standards_decay_%        0.52
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.376
_exptl_absorpt_correction_T_max  0.65779
_exptl_absorpt_correction_T_min  0.27857
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 Absorption corrections were made using the SHELXTL Version 5 software.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.409
_refine_ls_goodness_of_fit_ref   1.760
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.472
_refine_ls_restrained_S_obs      1.760
_refine_ls_R_factor_all          0.1971
_refine_ls_R_factor_gt           0.1093
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2861
_refine_ls_wR_factor_ref         0.2428
_reflns_number_gt                2405
_reflns_number_total             4456
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic025869s_s2_1.cif
_cod_data_source_block           1(EtOH)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1605.7(7)
_cod_database_code               4318796
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Fe Fe 0.5000 0.0000 1.0000 0.0489(7) Uani 1 d S .
Cl1 Cl 0.7598(4) 0.2660(4) 0.7042(3) 0.1253(14) Uani 1 d . .
Cl2 Cl 0.6854(6) -0.1138(5) 0.6203(5) 0.207(3) Uani 1 d . .
Cl3 Cl 0.1075(3) 0.2071(3) 0.6819(3) 0.1088(12) Uani 1 d . .
Cl4 Cl 0.2335(4) 0.4773(4) 0.8967(4) 0.159(2) Uani 1 d . .
O1 O 1.0283(10) -0.2320(14) 1.0796(12) 0.176(7) Uani 1 d . .
O2 O 1.0055(12) -0.3598(15) 1.0062(11) 0.238(10) Uani 1 d . .
O3 O 0.9658(9) -0.0103(14) 0.7937(10) 0.158(5) Uani 1 d . .
O4 O 0.9611(13) -0.1606(9) 0.7514(11) 0.237(10) Uani 1 d . .
O5 O 0.5337(9) 0.3655(10) 0.4898(8) 0.138(5) Uani 1 d . .
O6 O 0.5249(9) 0.1983(14) 0.4726(8) 0.143(5) Uani 1 d . .
O7 O 0.2628(8) 0.3913(10) 0.5049(7) 0.134(4) Uani 1 d . .
O8 O 0.2860(8) 0.4925(8) 0.6095(9) 0.121(4) Uani 1 d . .
N1 N 0.6637(6) -0.0824(6) 0.9598(5) 0.049(2) Uani 1 d . .
N2 N 0.4671(6) 0.1281(6) 0.8331(5) 0.047(2) Uani 1 d . .
N3 N 0.9745(10) -0.2691(14) 1.0263(10) 0.108(5) Uani 1 d . .
N4 N 0.9293(10) -0.0934(11) 0.8002(11) 0.115(5) Uani 1 d . .
N5 N 0.5203(8) 0.2682(11) 0.5251(8) 0.083(3) Uani 1 d . .
N6 N 0.3028(7) 0.3985(10) 0.5877(8) 0.078(3) Uani 1 d . .
C1 C 0.7477(7) -0.1756(8) 1.0390(7) 0.050(2) Uani 1 d . .
C2 C 0.8557(7) -0.1892(8) 0.9806(8) 0.055(3) Uani 1 d . .
C3 C 0.8359(8) -0.1079(8) 0.8745(7) 0.058(3) Uani 1 d . .
C4 C 0.7127(7) -0.0380(7) 0.8581(7) 0.050(2) Uani 1 d . .
C5 C 0.6581(7) 0.0546(7) 0.7584(7) 0.045(2) Uani 1 d . .
C6 C 0.5426(7) 0.1303(7) 0.7467(6) 0.047(2) Uani 1 d . .
C7 C 0.4836(8) 0.2287(8) 0.6440(7) 0.056(3) Uani 1 d . .
C8 C 0.3800(8) 0.2857(8) 0.6724(7) 0.055(3) Uani 1 d . .
C9 C 0.3660(7) 0.2230(7) 0.7898(7) 0.044(2) Uani 1 d . .
C10 C 0.2654(7) 0.2456(8) 0.8499(7) 0.051(2) Uani 1 d . .
C11 C 0.7264(8) 0.0784(8) 0.6531(7) 0.054(3) Uani 1 d . .
C12 C 0.7746(8) 0.1732(9) 0.6218(8) 0.064(3) Uani 1 d . .
C13 C 0.8383(10) 0.1968(12) 0.5242(10) 0.093(4) Uani 1 d . .
H13 H 0.8694(10) 0.2625(12) 0.5030(10) 0.111 Uiso 1 calc R .
C14 C 0.8531(13) 0.1223(17) 0.4625(12) 0.115(6) Uani 1 d . .
H14 H 0.8953(13) 0.1371(17) 0.3975(12) 0.138 Uiso 1 calc R .
C15 C 0.8095(15) 0.0269(17) 0.4907(13) 0.131(6) Uani 1 d . .
H15 H 0.8222(15) -0.0240(17) 0.4465(13) 0.157 Uiso 1 calc R .
C16 C 0.7452(12) 0.0052(11) 0.5867(11) 0.101(4) Uani 1 d . .
C17 C 0.1625(7) 0.3502(8) 0.7856(7) 0.048(2) Uani 1 d . .
C18 C 0.0861(8) 0.3416(8) 0.7076(8) 0.056(3) Uani 1 d . .
C19 C -0.0094(9) 0.4395(11) 0.6515(8) 0.070(3) Uani 1 d . .
H19 H -0.0613(9) 0.4320(11) 0.6010(8) 0.083 Uiso 1 calc R .
C20 C -0.0263(11) 0.5458(12) 0.6712(10) 0.091(4) Uani 1 d . .
H20 H -0.0909(11) 0.6113(12) 0.6337(10) 0.109 Uiso 1 calc R .
C21 C 0.0474(12) 0.5603(10) 0.7435(11) 0.096(4) Uani 1 d . .
H21 H 0.0353(12) 0.6355(10) 0.7535(11) 0.115 Uiso 1 calc R .
C22 C 0.1425(10) 0.4602(10) 0.8034(9) 0.077(3) Uani 1 d . .
O9 O 0.4213(10) -0.1158(10) 0.9479(9) 0.105(4) Uani 1 d . .
C23 C 0.3636(22) -0.1404(19) 0.8886(15) 0.185(13) Uani 1 d . .
H23A H 0.4110(22) -0.2114(19) 0.8719(15) 0.222 Uiso 1 calc R 1
H23B H 0.3420(22) -0.0729(19) 0.8155(15) 0.222 Uiso 1 calc R 1
C24 C 0.2624(39) -0.1654(37) 0.9332(37) 0.192(18) Uiso 0.50 d P 1
H24A H 0.2221(39) -0.1843(37) 0.8781(37) 0.288 Uiso 0.50 calc PR 1
H24B H 0.2130(39) -0.0950(37) 0.9478(37) 0.288 Uiso 0.50 calc PR 1
H24C H 0.2822(39) -0.2339(37) 1.0044(37) 0.288 Uiso 0.50 calc PR 1
C25 C 0.3985(33) -0.1146(30) 0.7663(28) 0.155(13) Uiso 0.50 d P 2
H25A H 0.3485(33) -0.1365(30) 0.7222(28) 0.232 Uiso 0.50 calc PR 2
H25B H 0.4778(33) -0.1617(30) 0.7670(28) 0.232 Uiso 0.50 calc PR 2
H25C H 0.3916(33) -0.0289(30) 0.7315(28) 0.232 Uiso 0.50 calc PR 2
C26 C 0.5424(38) -0.3602(50) 1.8847(30) 0.302(43) Uani 0.50 d P .
H26A H 0.4894(38) -0.2814(50) 1.8396(30) 0.363 Uiso 0.50 calc PR .
H26B H 0.5559(38) -0.3736(50) 1.9664(30) 0.363 Uiso 0.50 calc PR .
Cl5 Cl 0.6725(27) -0.4390(24) 1.8058(17) 0.374(13) Uani 0.50 d P .
Cl6 Cl 0.5476(24) -0.5100(43) 1.8366(21) 0.549(29) Uani 0.50 d P .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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
_geom_angle_publ_flag
N1 Fe N1 180.0 2_657 . ?
N1 Fe N2 89.9(2) 2_657 2_657 ?
N1 Fe N2 90.1(2) . 2_657 ?
N1 Fe N2 90.1(2) 2_657 . ?
N1 Fe N2 89.9(2) . . ?
N2 Fe N2 180.0 2_657 . ?
N1 Fe O9 87.1(4) 2_657 . ?
N1 Fe O9 92.9(4) . . ?
N2 Fe O9 89.0(3) 2_657 . ?
N2 Fe O9 91.0(3) . . ?
N1 Fe O9 92.9(4) 2_657 2_657 ?
N1 Fe O9 87.1(4) . 2_657 ?
N2 Fe O9 91.0(3) 2_657 2_657 ?
N2 Fe O9 89.0(3) . 2_657 ?
O9 Fe O9 179.999(1) . 2_657 ?
C4 N1 C1 109.4(6) . . ?
C4 N1 Fe 125.1(5) . . ?
C1 N1 Fe 124.4(5) . . ?
C6 N2 C9 108.9(6) . . ?
C6 N2 Fe 125.1(5) . . ?
C9 N2 Fe 126.0(5) . . ?
O2 N3 O1 127.4(15) . . ?
O2 N3 C2 117.1(17) . . ?
O1 N3 C2 115.5(15) . . ?
O4 N4 O3 125.2(13) . . ?
O4 N4 C3 118.4(15) . . ?
O3 N4 C3 116.4(14) . . ?
O5 N5 O6 127.6(12) . . ?
O5 N5 C7 117.0(12) . . ?
O6 N5 C7 115.2(11) . . ?
O7 N6 O8 124.9(11) . . ?
O7 N6 C8 118.1(12) . . ?
O8 N6 C8 117.0(11) . . ?
C10 C1 N1 127.9(7) 2_657 . ?
C10 C1 C2 125.8(8) 2_657 . ?
N1 C1 C2 106.3(7) . . ?
C3 C2 C1 109.3(7) . . ?
C3 C2 N3 120.8(8) . . ?
C1 C2 N3 129.7(8) . . ?
C2 C3 N4 121.3(8) . . ?
C2 C3 C4 107.6(7) . . ?
N4 C3 C4 130.8(8) . . ?
C5 C4 N1 127.3(7) . . ?
C5 C4 C3 125.3(8) . . ?
N1 C4 C3 107.4(7) . . ?
C4 C5 C6 125.1(7) . . ?
C4 C5 C11 117.9(7) . . ?
C6 C5 C11 117.0(7) . . ?
N2 C6 C5 126.5(7) . . ?
N2 C6 C7 107.1(7) . . ?
C5 C6 C7 126.4(7) . . ?
C8 C7 C6 107.6(7) . . ?
C8 C7 N5 122.0(8) . . ?
C6 C7 N5 130.4(8) . . ?
C7 C8 C9 109.2(7) . . ?
C7 C8 N6 120.7(8) . . ?
C9 C8 N6 130.1(8) . . ?
N2 C9 C10 125.5(7) . . ?
N2 C9 C8 107.1(7) . . ?
C10 C9 C8 127.2(7) . . ?
C1 C10 C9 125.2(7) 2_657 . ?
C1 C10 C17 117.4(7) 2_657 . ?
C9 C10 C17 117.4(7) . . ?
C16 C11 C12 117.3(9) . . ?
C16 C11 C5 121.7(10) . . ?
C12 C11 C5 121.0(9) . . ?
C11 C12 C13 121.8(11) . . ?
C11 C12 Cl1 120.2(7) . . ?
C13 C12 Cl1 118.0(10) . . ?
C14 C13 C12 118.0(13) . . ?
C13 C14 C15 122.5(14) . . ?
C14 C15 C16 119.1(15) . . ?
C11 C16 C15 121.3(13) . . ?
C11 C16 Cl2 119.5(9) . . ?
C15 C16 Cl2 119.2(12) . . ?
C22 C17 C18 118.0(8) . . ?
C22 C17 C10 119.1(10) . . ?
C18 C17 C10 122.8(9) . . ?
C19 C18 C17 121.2(9) . . ?
C19 C18 Cl3 118.9(9) . . ?
C17 C18 Cl3 119.9(7) . . ?
C20 C19 C18 119.1(11) . . ?
C19 C20 C21 122.1(11) . . ?
C20 C21 C22 119.0(11) . . ?
C17 C22 C21 120.5(11) . . ?
C17 C22 Cl4 120.4(8) . . ?
C21 C22 Cl4 119.1(9) . . ?
C23 O9 Fe 156.5(15) . . ?
O9 C23 C24 116.3(25) . . ?
O9 C23 C25 113.3(27) . . ?
Cl5 C26 Cl6 55.7(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe N1 2.069(6) 2_657 ?
Fe N1 2.069(6) . ?
Fe N2 2.078(6) 2_657 ?
Fe N2 2.078(6) . ?
Fe O9 2.153(11) . ?
Fe O9 2.153(11) 2_657 ?
Cl1 C12 1.718(11) . ?
Cl2 C16 1.714(14) . ?
Cl3 C18 1.709(10) . ?
Cl4 C22 1.697(11) . ?
O1 N3 1.19(2) . ?
O2 N3 1.16(2) . ?
O3 N4 1.19(2) . ?
O4 N4 1.14(2) . ?
O5 N5 1.168(13) . ?
O6 N5 1.212(14) . ?
O7 N6 1.170(13) . ?
O8 N6 1.216(13) . ?
N1 C4 1.375(10) . ?
N1 C1 1.378(10) . ?
N2 C6 1.379(9) . ?
N2 C9 1.380(9) . ?
N3 C2 1.475(13) . ?
N4 C3 1.442(12) . ?
N5 C7 1.475(11) . ?
N6 C8 1.477(12) . ?
C1 C10 1.376(11) 2_657 ?
C1 C2 1.464(11) . ?
C2 C3 1.320(11) . ?
C3 C4 1.461(11) . ?
C4 C5 1.372(11) . ?
C5 C6 1.408(11) . ?
C5 C11 1.505(11) . ?
C6 C7 1.437(11) . ?
C7 C8 1.342(12) . ?
C8 C9 1.417(11) . ?
C9 C10 1.410(11) . ?
C10 C1 1.376(11) 2_657 ?
C10 C17 1.497(11) . ?
C11 C16 1.364(14) . ?
C11 C12 1.368(13) . ?
C12 C13 1.398(13) . ?
C13 C14 1.33(2) . ?
C14 C15 1.34(2) . ?
C15 C16 1.39(2) . ?
C17 C22 1.375(13) . ?
C17 C18 1.386(13) . ?
C18 C19 1.383(13) . ?
C19 C20 1.347(15) . ?
C20 C21 1.35(2) . ?
C21 C22 1.403(14) . ?
O9 C23 1.17(3) . ?
C23 C24 1.39(4) . ?
C23 C25 1.50(3) . ?
C26 Cl5 2.00(4) . ?
C26 Cl6 2.07(7) . ?
