#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/20/4112057.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_4112057
loop_
_publ_author_name
'Paul D. Oldenburg'
'Albert A. Shteinman'
'Lawrence Que'
_publ_section_title
;
 Iron-Catalyzed Olefincis-Dihydroxylation Using a Bio-Inspired
 N,N,O-Ligand
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15672
_journal_page_last               15673
_journal_paper_doi               10.1021/ja054947i
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C36 H30 Fe N6 O2, 2(C F3 O3 S)'
_chemical_formula_sum            'C38 H30 F6 Fe N6 O8 S2'
_chemical_formula_weight         932.65
_chemical_name_common            04108
_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-97
_cell_angle_alpha                110.064(2)
_cell_angle_beta                 95.696(3)
_cell_angle_gamma                91.331(3)
_cell_formula_units_Z            1
_cell_length_a                   9.0468(14)
_cell_length_b                   10.5152(16)
_cell_length_c                   10.7334(16)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.34
_cell_volume                     952.6(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3355
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, R. Blessing, 1995'
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0228P)²+1.3407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2786
_reflns_number_total             3355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja054947isi20050722_043827.cif
_cod_data_source_block           04108a
_cod_database_code               4112057
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.5000 0.5000 0.5000 0.02234(14) Uani 1 2 d S
S1 S 0.79162(8) 1.02651(7) 1.15719(7) 0.03199(18) Uani 1 1 d .
O4 O 0.9117(2) 1.1274(2) 1.1887(2) 0.0456(6) Uani 1 1 d .
O3 O 0.7377(2) 0.9660(2) 1.0175(2) 0.0411(5) Uani 1 1 d .
F3 F 0.7773(2) 0.78093(18) 1.1673(2) 0.0546(5) Uani 1 1 d .
O2 O 0.6767(2) 1.0588(2) 1.2445(2) 0.0463(6) Uani 1 1 d .
O1 O 0.4607(2) 0.54690(18) 0.69444(17) 0.0295(4) Uani 1 1 d .
N1 N 0.6345(2) 0.7088(2) 0.8273(2) 0.0262(5) Uani 1 1 d .
H1A H 0.6562 0.7676 0.9088 0.031 Uiso 1 1 calc R
N3 N 0.7288(2) 0.4721(2) 0.5664(2) 0.0254(5) Uani 1 1 d .
N2 N 0.5837(2) 0.7053(2) 0.5320(2) 0.0258(5) Uani 1 1 d .
F2 F 0.9380(2) 0.9182(2) 1.3164(2) 0.0650(6) Uani 1 1 d .
F1 F 0.9839(2) 0.8393(2) 1.1127(3) 0.0758(7) Uani 1 1 d .
C3 C 0.9543(3) 0.5505(3) 0.7134(3) 0.0309(6) Uani 1 1 d .
H3B H 1.0091 0.6191 0.7867 0.037 Uiso 1 1 calc R
C12 C 0.5080(3) 0.6337(3) 0.8055(2) 0.0239(6) Uani 1 1 d .
C1 C 0.7439(3) 0.7065(3) 0.7329(3) 0.0247(6) Uani 1 1 d .
H1B H 0.8301 0.7674 0.7890 0.030 Uiso 1 1 calc R
C7 C 0.6918(3) 0.7704(3) 0.6303(3) 0.0247(6) Uani 1 1 d .
C2 C 0.8089(3) 0.5694(3) 0.6700(2) 0.0240(6) Uani 1 1 d .
C18 C 0.3365(3) 0.5382(3) 0.9201(3) 0.0304(6) Uani 1 1 d .
H18A H 0.3353 0.4547 0.8478 0.037 Uiso 1 1 calc R
C17 C 0.2547(3) 0.5476(3) 1.0245(3) 0.0367(7) Uani 1 1 d .
H17A H 0.1971 0.4707 1.0242 0.044 Uiso 1 1 calc R
C13 C 0.4212(3) 0.6512(3) 0.9204(2) 0.0245(6) Uani 1 1 d .
C14 C 0.4225(3) 0.7729(3) 1.0255(3) 0.0316(6) Uani 1 1 d .
H14A H 0.4798 0.8501 1.0263 0.038 Uiso 1 1 calc R
C5 C 0.9367(3) 0.3319(3) 0.5426(3) 0.0341(7) Uani 1 1 d .
H5A H 0.9784 0.2490 0.4967 0.041 Uiso 1 1 calc R
C8 C 0.7613(3) 0.8920(3) 0.6377(3) 0.0313(6) Uani 1 1 d .
H8A H 0.8355 0.9375 0.7094 0.038 Uiso 1 1 calc R
C15 C 0.3394(3) 0.7812(3) 1.1297(3) 0.0409(8) Uani 1 1 d .
H15A H 0.3395 0.8647 1.2017 0.049 Uiso 1 1 calc R
C9 C 0.7219(3) 0.9461(3) 0.5399(3) 0.0364(7) Uani 1 1 d .
H9A H 0.7696 1.0288 0.5430 0.044 Uiso 1 1 calc R
C10 C 0.6128(3) 0.8794(3) 0.4378(3) 0.0338(7) Uani 1 1 d .
H10A H 0.5845 0.9142 0.3687 0.041 Uiso 1 1 calc R
C4 C 1.0181(3) 0.4304(3) 0.6483(3) 0.0376(7) Uani 1 1 d .
H4B H 1.1173 0.4162 0.6766 0.045 Uiso 1 1 calc R
C11 C 0.5459(3) 0.7610(3) 0.4383(3) 0.0308(6) Uani 1 1 d .
H11A H 0.4690 0.7159 0.3690 0.037 Uiso 1 1 calc R
C6 C 0.7935(3) 0.3565(3) 0.5050(3) 0.0293(6) Uani 1 1 d .
H6A H 0.7373 0.2885 0.4321 0.035 Uiso 1 1 calc R
C16 C 0.2567(3) 0.6694(3) 1.1297(3) 0.0403(8) Uani 1 1 d .
H16A H 0.2011 0.6759 1.2020 0.048 Uiso 1 1 calc R
C19 C 0.8767(3) 0.8844(3) 1.1884(3) 0.0397(7) 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 180.0 2_666 .
O1 Fe1 N2 92.93(8) 2_666 2_666
O1 Fe1 N2 87.07(8) . 2_666
O1 Fe1 N2 87.07(8) 2_666 .
O1 Fe1 N2 92.93(8) . .
N2 Fe1 N2 180.000(1) 2_666 .
O1 Fe1 N3 93.42(8) 2_666 .
O1 Fe1 N3 86.58(8) . .
N2 Fe1 N3 95.62(8) 2_666 .
N2 Fe1 N3 84.38(8) . .
O1 Fe1 N3 86.58(8) 2_666 2_666
O1 Fe1 N3 93.42(8) . 2_666
N2 Fe1 N3 84.38(8) 2_666 2_666
N2 Fe1 N3 95.62(8) . 2_666
N3 Fe1 N3 180.000(1) . 2_666
O4 S1 O2 115.40(14) . .
O4 S1 O3 115.47(13) . .
O2 S1 O3 114.41(14) . .
O4 S1 C19 104.00(14) . .
O2 S1 C19 104.03(14) . .
O3 S1 C19 100.96(14) . .
C12 O1 Fe1 137.44(17) . .
C12 N1 C1 128.6(2) . .
C12 N1 H1A 115.7 . .
C1 N1 H1A 115.7 . .
C6 N3 C2 118.4(2) . .
C6 N3 Fe1 120.37(17) . .
C2 N3 Fe1 121.24(17) . .
C7 N2 C11 117.8(2) . .
C7 N2 Fe1 121.96(18) . .
C11 N2 Fe1 119.24(18) . .
C4 C3 C2 119.3(3) . .
C4 C3 H3B 120.4 . .
C2 C3 H3B 120.4 . .
O1 C12 N1 123.4(2) . .
O1 C12 C13 118.7(2) . .
N1 C12 C13 117.9(2) . .
N1 C1 C7 113.7(2) . .
N1 C1 C2 114.9(2) . .
C7 C1 C2 112.4(2) . .
N1 C1 H1B 104.8 . .
C7 C1 H1B 104.8 . .
C2 C1 H1B 104.8 . .
N2 C7 C8 121.7(3) . .
N2 C7 C1 119.3(2) . .
C8 C7 C1 118.9(2) . .
N3 C2 C3 121.1(2) . .
N3 C2 C1 119.5(2) . .
C3 C2 C1 119.2(2) . .
C17 C18 C13 120.2(3) . .
C17 C18 H18A 119.9 . .
C13 C18 H18A 119.9 . .
C18 C17 C16 119.8(3) . .
C18 C17 H17A 120.1 . .
C16 C17 H17A 120.1 . .
C14 C13 C18 119.8(2) . .
C14 C13 C12 122.8(2) . .
C18 C13 C12 117.4(2) . .
C13 C14 C15 119.5(3) . .
C13 C14 H14A 120.3 . .
C15 C14 H14A 120.3 . .
C6 C5 C4 118.4(3) . .
C6 C5 H5A 120.8 . .
C4 C5 H5A 120.8 . .
C9 C8 C7 119.4(3) . .
C9 C8 H8A 120.3 . .
C7 C8 H8A 120.3 . .
C16 C15 C14 120.6(3) . .
C16 C15 H15A 119.7 . .
C14 C15 H15A 119.7 . .
C8 C9 C10 119.4(3) . .
C8 C9 H9A 120.3 . .
C10 C9 H9A 120.3 . .
C11 C10 C9 118.2(3) . .
C11 C10 H10A 120.9 . .
C9 C10 H10A 120.9 . .
C5 C4 C3 119.5(3) . .
C5 C4 H4B 120.2 . .
C3 C4 H4B 120.2 . .
N2 C11 C10 123.5(3) . .
N2 C11 H11A 118.3 . .
C10 C11 H11A 118.3 . .
N3 C6 C5 123.3(3) . .
N3 C6 H6A 118.3 . .
C5 C6 H6A 118.3 . .
C15 C16 C17 120.1(3) . .
C15 C16 H16A 120.0 . .
C17 C16 H16A 120.0 . .
F1 C19 F3 108.2(3) . .
F1 C19 F2 106.8(3) . .
F3 C19 F2 106.0(2) . .
F1 C19 S1 111.9(2) . .
F3 C19 S1 111.8(2) . .
F2 C19 S1 111.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O1 2.0431(17) 2_666
Fe1 O1 2.0431(17) .
Fe1 N2 2.171(2) 2_666
Fe1 N2 2.171(2) .
Fe1 N3 2.181(2) .
Fe1 N3 2.181(2) 2_666
S1 O4 1.431(2) .
S1 O2 1.438(2) .
S1 O3 1.441(2) .
S1 C19 1.812(3) .
F3 C19 1.338(3) .
O1 C12 1.253(3) .
N1 C12 1.329(3) .
N1 C1 1.480(3) .
N1 H1A 0.8800 .
N3 C6 1.347(3) .
N3 C2 1.354(3) .
N2 C7 1.344(3) .
N2 C11 1.347(3) .
F2 C19 1.352(4) .
F1 C19 1.318(4) .
C3 C4 1.388(4) .
C3 C2 1.393(4) .
C3 H3B 0.9500 .
C12 C13 1.488(4) .
C1 C7 1.518(4) .
C1 C2 1.527(4) .
C1 H1B 1.0000 .
C7 C8 1.386(4) .
C18 C17 1.381(4) .
C18 C13 1.398(4) .
C18 H18A 0.9500 .
C17 C16 1.385(4) .
C17 H17A 0.9500 .
C13 C14 1.384(4) .
C14 C15 1.388(4) .
C14 H14A 0.9500 .
C5 C6 1.375(4) .
C5 C4 1.377(4) .
C5 H5A 0.9500 .
C8 C9 1.377(4) .
C8 H8A 0.9500 .
C15 C16 1.379(4) .
C15 H15A 0.9500 .
C9 C10 1.376(4) .
C9 H9A 0.9500 .
C10 C11 1.374(4) .
C10 H10A 0.9500 .
C4 H4B 0.9500 .
C11 H11A 0.9500 .
C6 H6A 0.9500 .
C16 H16A 0.9500 .
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
O1 Fe1 O1 C12 -140(100) 2_666
N2 Fe1 O1 C12 155.6(3) 2_666
N2 Fe1 O1 C12 -24.4(3) .
N3 Fe1 O1 C12 59.8(3) .
N3 Fe1 O1 C12 -120.2(3) 2_666
O1 Fe1 N3 C6 -52.4(2) 2_666
O1 Fe1 N3 C6 127.6(2) .
N2 Fe1 N3 C6 40.8(2) 2_666
N2 Fe1 N3 C6 -139.2(2) .
N3 Fe1 N3 C6 123(100) 2_666
O1 Fe1 N3 C2 127.95(19) 2_666
O1 Fe1 N3 C2 -52.05(19) .
N2 Fe1 N3 C2 -138.77(19) 2_666
N2 Fe1 N3 C2 41.23(19) .
N3 Fe1 N3 C2 -56(100) 2_666
O1 Fe1 N2 C7 -127.8(2) 2_666
O1 Fe1 N2 C7 52.2(2) .
N2 Fe1 N2 C7 64(100) 2_666
N3 Fe1 N2 C7 -34.09(19) .
N3 Fe1 N2 C7 145.91(19) 2_666
O1 Fe1 N2 C11 40.5(2) 2_666
O1 Fe1 N2 C11 -139.5(2) .
N2 Fe1 N2 C11 -128(100) 2_666
N3 Fe1 N2 C11 134.2(2) .
N3 Fe1 N2 C11 -45.8(2) 2_666
Fe1 O1 C12 N1 -16.8(4) .
Fe1 O1 C12 C13 165.27(18) .
C1 N1 C12 O1 -1.0(4) .
C1 N1 C12 C13 176.9(2) .
C12 N1 C1 C7 73.8(3) .
C12 N1 C1 C2 -57.8(3) .
C11 N2 C7 C8 1.1(4) .
Fe1 N2 C7 C8 169.53(19) .
C11 N2 C7 C1 -176.3(2) .
Fe1 N2 C7 C1 -7.9(3) .
N1 C1 C7 N2 -71.7(3) .
C2 C1 C7 N2 61.1(3) .
N1 C1 C7 C8 110.9(3) .
C2 C1 C7 C8 -116.3(3) .
C6 N3 C2 C3 -0.5(4) .
Fe1 N3 C2 C3 179.08(19) .
C6 N3 C2 C1 174.2(2) .
Fe1 N3 C2 C1 -6.1(3) .
C4 C3 C2 N3 0.5(4) .
C4 C3 C2 C1 -174.3(2) .
N1 C1 C2 N3 79.6(3) .
C7 C1 C2 N3 -52.6(3) .
N1 C1 C2 C3 -105.5(3) .
C7 C1 C2 C3 122.3(3) .
C13 C18 C17 C16 0.0(4) .
C17 C18 C13 C14 -0.2(4) .
C17 C18 C13 C12 179.4(2) .
O1 C12 C13 C14 -151.8(3) .
N1 C12 C13 C14 30.1(4) .
O1 C12 C13 C18 28.6(4) .
N1 C12 C13 C18 -149.5(2) .
C18 C13 C14 C15 0.0(4) .
C12 C13 C14 C15 -179.6(3) .
N2 C7 C8 C9 -1.8(4) .
C1 C7 C8 C9 175.6(2) .
C13 C14 C15 C16 0.4(4) .
C7 C8 C9 C10 0.8(4) .
C8 C9 C10 C11 0.7(4) .
C6 C5 C4 C3 0.0(4) .
C2 C3 C4 C5 -0.2(4) .
C7 N2 C11 C10 0.6(4) .
Fe1 N2 C11 C10 -168.2(2) .
C9 C10 C11 N2 -1.5(4) .
C2 N3 C6 C5 0.2(4) .
Fe1 N3 C6 C5 -179.4(2) .
C4 C5 C6 N3 0.0(4) .
C14 C15 C16 C17 -0.7(5) .
C18 C17 C16 C15 0.5(5) .
O4 S1 C19 F1 -60.4(3) .
O2 S1 C19 F1 178.5(2) .
O3 S1 C19 F1 59.6(2) .
O4 S1 C19 F3 178.1(2) .
O2 S1 C19 F3 56.9(3) .
O3 S1 C19 F3 -61.9(3) .
O4 S1 C19 F2 59.4(2) .
O2 S1 C19 F2 -61.8(2) .
O3 S1 C19 F2 179.4(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139118893
