#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/46/4114690.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_4114690
loop_
_publ_author_name
'Kui Chen'
'Miquel Costas'
'Jinheung Kim'
'Adrianne K. Tipton'
'Lawrence Que'
_publ_section_title
;
 Olefin Cis-Dihydroxylation versus Epoxidation by Non-Heme Iron Catalysts:
 Two Faces of an FeIII-OOH Coin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3026
_journal_page_last               3035
_journal_paper_doi               10.1021/ja0120025
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C20 H26 F6 Fe N4 O6 S2'
_chemical_formula_weight         652.42
_chemical_name_common            00309
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 117.312(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.232(2)
_cell_length_b                   9.540(1)
_cell_length_c                   18.263(2)
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    293(2)
_cell_volume                     2667.6(5)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7980
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.778161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0369
_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)+(0.0543P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2190
_reflns_number_total             3028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0120025_2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4114690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 1.0000 0.05617(4) 0.7500 0.02650(14) Uani 1 2 d S
S1 S 0.99021(4) 0.31101(6) 0.86856(3) 0.03062(16) Uani 1 1 d .
F1 F 0.85612(9) 0.46992(14) 0.77564(9) 0.0465(4) Uani 1 1 d .
F2 F 0.83406(10) 0.33550(17) 0.85803(12) 0.0608(5) Uani 1 1 d .
F3 F 0.91548(12) 0.51858(17) 0.90463(11) 0.0604(5) Uani 1 1 d .
O1 O 0.95146(10) 0.20362(16) 0.80456(10) 0.0327(4) Uani 1 1 d .
O2 O 1.02005(11) 0.25829(19) 0.95070(10) 0.0439(4) Uani 1 1 d .
O3 O 1.04586(10) 0.40786(18) 0.85536(10) 0.0406(4) Uani 1 1 d .
N1 N 1.11659(12) 0.0369(2) 0.87837(12) 0.0327(5) Uani 1 1 d .
N2 N 0.96470(12) -0.1206(2) 0.80788(13) 0.0382(5) Uani 1 1 d .
C1 C 1.21842(15) 0.1857(3) 0.85478(16) 0.0383(6) Uani 1 1 d .
H1A H 1.2093 0.1375 0.8053 0.057 Uiso 1 1 calc R
H1B H 1.2781 0.2160 0.8836 0.057 Uiso 1 1 calc R
H1C H 1.1805 0.2656 0.8409 0.057 Uiso 1 1 calc R
C2 C 1.19897(15) 0.0893(3) 0.90826(15) 0.0355(5) Uani 1 1 d .
C3 C 1.26272(18) 0.0577(3) 0.98726(16) 0.0473(7) Uani 1 1 d .
H3 H 1.3188 0.0939 1.0063 0.057 Uiso 1 1 calc R
C4 C 1.2431(2) -0.0268(3) 1.03723(18) 0.0573(8) Uani 1 1 d .
H4 H 1.2857 -0.0493 1.0900 0.069 Uiso 1 1 calc R
C5 C 1.1596(2) -0.0776(3) 1.00829(18) 0.0536(8) Uani 1 1 d .
H5 H 1.1448 -0.1342 1.0414 0.064 Uiso 1 1 calc R
C6 C 1.09773(17) -0.0435(3) 0.92931(16) 0.0400(6) Uani 1 1 d .
C7 C 1.00430(16) -0.0903(3) 0.89709(17) 0.0457(7) Uani 1 1 d .
H7A H 1.0021 -0.1738 0.9264 0.055 Uiso 1 1 calc R
H7B H 0.9710 -0.0174 0.9070 0.055 Uiso 1 1 calc R
C8 C 1.00511(17) -0.2480(3) 0.79309(17) 0.0474(7) Uani 1 1 d .
H8A H 0.9776 -0.3309 0.8014 0.057 Uiso 1 1 calc R
H8B H 1.0667 -0.2508 0.8322 0.057 Uiso 1 1 calc R
C9 C 0.86898(16) -0.1409(3) 0.7755(2) 0.0526(8) Uani 1 1 d .
H9A H 0.8585 -0.2195 0.8026 0.079 Uiso 1 1 calc R
H9B H 0.8429 -0.1583 0.7172 0.079 Uiso 1 1 calc R
H9C H 0.8438 -0.0581 0.7857 0.079 Uiso 1 1 calc R
C10 C 0.89391(16) 0.4142(3) 0.85023(16) 0.0383(6) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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
O1 Fe1 O1 96.19(9) 2_756 .
O1 Fe1 N2 171.25(6) 2_756 .
O1 Fe1 N2 91.56(7) . .
O1 Fe1 N2 91.56(7) 2_756 2_756
O1 Fe1 N2 171.25(6) . 2_756
N2 Fe1 N2 81.03(11) . 2_756
O1 Fe1 N1 100.69(6) 2_756 .
O1 Fe1 N1 85.50(6) . .
N2 Fe1 N1 75.81(7) . .
N2 Fe1 N1 97.09(7) 2_756 .
O1 Fe1 N1 85.50(6) 2_756 2_756
O1 Fe1 N1 100.69(6) . 2_756
N2 Fe1 N1 97.09(7) . 2_756
N2 Fe1 N1 75.81(7) 2_756 2_756
N1 Fe1 N1 170.81(10) . 2_756
O3 S1 O2 117.16(11) . .
O3 S1 O1 114.39(10) . .
O2 S1 O1 113.74(10) . .
O3 S1 C10 104.16(11) . .
O2 S1 C10 103.91(11) . .
O1 S1 C10 100.82(10) . .
S1 O1 Fe1 135.24(9) . .
C6 N1 C2 117.8(2) . .
C6 N1 Fe1 111.96(15) . .
C2 N1 Fe1 130.17(16) . .
C7 N2 C8 110.1(2) . .
C7 N2 C9 109.3(2) . .
C8 N2 C9 110.4(2) . .
C7 N2 Fe1 106.71(15) . .
C8 N2 Fe1 106.34(14) . .
C9 N2 Fe1 113.93(15) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 121.3(2) . .
N1 C2 C1 118.1(2) . .
C3 C2 C1 120.5(2) . .
C4 C3 C2 120.0(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 C5 119.1(3) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
C4 C5 C6 119.3(3) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
N1 C6 C5 122.4(2) . .
N1 C6 C7 116.7(2) . .
C5 C6 C7 120.8(2) . .
N2 C7 C6 111.0(2) . .
N2 C7 H7A 109.4 . .
C6 C7 H7A 109.4 . .
N2 C7 H7B 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
N2 C8 C8 110.57(18) . 2_756
N2 C8 H8A 109.5 . .
C8 C8 H8A 109.5 2_756 .
N2 C8 H8B 109.5 . .
C8 C8 H8B 109.5 2_756 .
H8A C8 H8B 108.1 . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
F1 C10 F3 107.7(2) . .
F1 C10 F2 107.3(2) . .
F3 C10 F2 107.8(2) . .
F1 C10 S1 112.51(16) . .
F3 C10 S1 110.33(18) . .
F2 C10 S1 111.08(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O1 2.1061(15) 2_756
Fe1 O1 2.1062(15) .
Fe1 N2 2.2189(19) .
Fe1 N2 2.2189(19) 2_756
Fe1 N1 2.2899(19) .
Fe1 N1 2.2900(19) 2_756
S1 O3 1.4295(17) .
S1 O2 1.4353(17) .
S1 O1 1.4647(16) .
S1 C10 1.823(2) .
F1 C10 1.322(3) .
F2 C10 1.335(3) .
F3 C10 1.334(3) .
N1 C6 1.356(3) .
N1 C2 1.361(3) .
N2 C7 1.478(3) .
N2 C8 1.485(3) .
N2 C9 1.487(3) .
C1 C2 1.487(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.387(4) .
C3 C4 1.372(4) .
C3 H3 0.9300 .
C4 C5 1.373(4) .
C4 H4 0.9300 .
C5 C6 1.382(4) .
C5 H5 0.9300 .
C6 C7 1.506(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C8 1.501(5) 2_756
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3 S1 O1 Fe1 53.21(17) . .
O2 S1 O1 Fe1 -85.11(15) . .
C10 S1 O1 Fe1 164.32(14) . .
O1 Fe1 O1 S1 -64.55(12) 2_756 .
N2 Fe1 O1 S1 111.37(14) . .
N2 Fe1 O1 S1 143.3(4) 2_756 .
N1 Fe1 O1 S1 35.74(14) . .
N1 Fe1 O1 S1 -151.12(14) 2_756 .
O1 Fe1 N1 C6 173.64(15) 2_756 .
O1 Fe1 N1 C6 78.18(16) . .
N2 Fe1 N1 C6 -14.57(15) . .
N2 Fe1 N1 C6 -93.41(16) 2_756 .
N1 Fe1 N1 C6 -54.54(15) 2_756 .
O1 Fe1 N1 C2 -8.5(2) 2_756 .
O1 Fe1 N1 C2 -103.9(2) . .
N2 Fe1 N1 C2 163.3(2) . .
N2 Fe1 N1 C2 84.5(2) 2_756 .
N1 Fe1 N1 C2 123.36(19) 2_756 .
O1 Fe1 N2 C7 99.4(5) 2_756 .
O1 Fe1 N2 C7 -52.90(15) . .
N2 Fe1 N2 C7 131.77(17) 2_756 .
N1 Fe1 N2 C7 32.06(14) . .
N1 Fe1 N2 C7 -153.88(14) 2_756 .
O1 Fe1 N2 C8 -18.0(6) 2_756 .
O1 Fe1 N2 C8 -170.36(16) . .
N2 Fe1 N2 C8 14.32(12) 2_756 .
N1 Fe1 N2 C8 -85.40(16) . .
N1 Fe1 N2 C8 88.67(16) 2_756 .
O1 Fe1 N2 C9 -139.8(4) 2_756 .
O1 Fe1 N2 C9 67.85(18) . .
N2 Fe1 N2 C9 -107.5(2) 2_756 .
N1 Fe1 N2 C9 152.81(19) . .
N1 Fe1 N2 C9 -33.13(19) 2_756 .
C6 N1 C2 C3 2.2(3) . .
Fe1 N1 C2 C3 -175.58(18) . .
C6 N1 C2 C1 -175.8(2) . .
Fe1 N1 C2 C1 6.4(3) . .
N1 C2 C3 C4 -0.6(4) . .
C1 C2 C3 C4 177.4(2) . .
C2 C3 C4 C5 -0.8(4) . .
C3 C4 C5 C6 0.7(4) . .
C2 N1 C6 C5 -2.4(4) . .
Fe1 N1 C6 C5 175.8(2) . .
C2 N1 C6 C7 175.2(2) . .
Fe1 N1 C6 C7 -6.7(3) . .
C4 C5 C6 N1 1.0(4) . .
C4 C5 C6 C7 -176.5(3) . .
C8 N2 C7 C6 68.9(2) . .
C9 N2 C7 C6 -169.7(2) . .
Fe1 N2 C7 C6 -46.1(2) . .
N1 C6 C7 N2 36.3(3) . .
C5 C6 C7 N2 -146.1(2) . .
C7 N2 C8 C8 -156.8(2) . 2_756
C9 N2 C8 C8 82.5(3) . 2_756
Fe1 N2 C8 C8 -41.5(3) . 2_756
O3 S1 C10 F1 57.9(2) . .
O2 S1 C10 F1 -178.91(17) . .
O1 S1 C10 F1 -60.90(19) . .
O3 S1 C10 F3 -62.40(19) . .
O2 S1 C10 F3 60.8(2) . .
O1 S1 C10 F3 178.80(17) . .
O3 S1 C10 F2 178.15(17) . .
O2 S1 C10 F2 -58.7(2) . .
O1 S1 C10 F2 59.35(19) . .
