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#$Date: 2017-03-04 07:18:20 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/57/4125774.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_4125774
loop_
_publ_author_name
'Lo, Julian C.'
'Kim, Dongyoung'
'Pan, Chung-Mao'
'Edwards, Jacob T.'
'Yabe, Yuki'
'Gui, Jinghan'
'Qin, Tian'
'Gutiérrez, Sara'
'Giacoboni, Jessica'
'Smith, Myles W.'
'Holland, Patrick L.'
'Baran, Phil S.'
_publ_section_title
;
 Fe-Catalyzed C-C Bond Construction from Olefins via Radicals.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2484
_journal_page_last               2503
_journal_paper_doi               10.1021/jacs.6b13155
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C18 H30 Fe O6'
_chemical_formula_sum            'C18 H30 Fe O6'
_chemical_formula_weight         398.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.126(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4305(11)
_cell_length_b                   11.1187(8)
_cell_length_c                   12.8932(9)
_cell_measurement_reflns_used    338
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     1986.0(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13589
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.619
_diffrn_reflns_theta_min         2.517
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0526P)²+1.5809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1806
_reflns_number_total             2291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b13155_si_003.cif
_cod_data_source_block           mini-16016
_cod_database_code               4125774
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.798
_shelx_estimated_absorpt_t_max   0.911
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.5000 0.5000 0.03016(13) Uani 1 2 d S . P C .
O11 O 0.43632(10) 0.39046(12) 0.36251(11) 0.0390(3) Uani 1 1 d . . . . .
O21 O 0.55847(10) 0.35175(11) 0.59720(10) 0.0343(3) Uani 1 1 d . . . . .
C11 C 0.38000(16) 0.2221(2) 0.24394(17) 0.0484(5) Uani 1 1 d . . . . .
H11A H 0.3110 0.2305 0.2226 0.073 Uiso 1 1 calc R U . . .
H11B H 0.3964 0.1366 0.2469 0.073 Uiso 1 1 calc R U . . .
H11C H 0.3950 0.2627 0.1863 0.073 Uiso 1 1 calc R U . . .
C21 C 0.43739(13) 0.27781(17) 0.35985(15) 0.0342(4) Uani 1 1 d . . . . .
C31 C 0.48632(14) 0.20480(17) 0.45474(18) 0.0386(4) Uani 1 1 d . . . . .
H31 H 0.4806 0.1204 0.4423 0.046 Uiso 1 1 calc R U . . .
C41 C 0.54306(13) 0.24425(16) 0.56656(15) 0.0312(4) Uani 1 1 d . . . . .
C51 C 0.58976(17) 0.15377(17) 0.66047(18) 0.0460(5) Uani 1 1 d . . . . .
H51A H 0.6592 0.1698 0.7009 0.069 Uiso 1 1 calc R U . . .
H51B H 0.5791 0.0729 0.6269 0.069 Uiso 1 1 calc R U . . .
H51C H 0.5616 0.1592 0.7152 0.069 Uiso 1 1 calc R U . . .
O10 O 0.37362(10) 0.48273(14) 0.53254(12) 0.0455(4) Uani 1 1 d . . . . .
C20 C 0.37049(16) 0.4246(2) 0.62804(17) 0.0472(5) Uani 1 1 d . . . . .
H20A H 0.4147 0.4645 0.7009 0.057 Uiso 1 1 calc R U . . .
H20B H 0.3901 0.3394 0.6313 0.057 Uiso 1 1 calc R U . . .
C30 C 0.26946(16) 0.4328(3) 0.6121(2) 0.0594(7) Uani 1 1 d . . . . .
H30A H 0.2645 0.4894 0.6685 0.071 Uiso 1 1 calc R U . . .
H30B H 0.2457 0.3529 0.6220 0.071 Uiso 1 1 calc R U . . .
C40 C 0.2133(2) 0.4773(3) 0.4923(2) 0.0788(10) Uani 1 1 d . . . . .
H40C H 0.1549 0.4276 0.4504 0.095 Uiso 0.5 1 calc R U P A 2
H40D H 0.1934 0.5620 0.4924 0.095 Uiso 0.5 1 calc R U P A 2
H40A H 0.1761 0.4108 0.4410 0.095 Uiso 0.5 1 calc R U P B 1
H40B H 0.1676 0.5408 0.4903 0.095 Uiso 0.5 1 calc R U P B 1
C5A C 0.2808(7) 0.5245(6) 0.4554(7) 0.0569(19) Uani 0.5 1 d . . P C 1
H5AA H 0.2645 0.4971 0.3759 0.068 Uiso 0.5 1 calc R U P C 1
H5AB H 0.2792 0.6135 0.4557 0.068 Uiso 0.5 1 calc R U P C 1
C5B C 0.2794(6) 0.4672(6) 0.4385(6) 0.0485(15) Uani 0.5 1 d . . P C 2
H5BA H 0.2736 0.3874 0.4020 0.058 Uiso 0.5 1 calc R U P C 2
H5BB H 0.2660 0.5303 0.3792 0.058 Uiso 0.5 1 calc R U P C 2
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'
Fe Fe 0.3463 0.8444 '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'
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
O11 Fe1 O11 180.00(9) . 5_666
O11 Fe1 O21 87.95(5) . .
O11 Fe1 O21 92.05(5) 5_666 .
O11 Fe1 O21 92.05(5) . 5_666
O11 Fe1 O21 87.95(5) 5_666 5_666
O21 Fe1 O21 180.0 . 5_666
O11 Fe1 O10 90.86(6) . 5_666
O11 Fe1 O10 89.14(6) 5_666 5_666
O21 Fe1 O10 89.90(5) . 5_666
O21 Fe1 O10 90.10(5) 5_666 5_666
O11 Fe1 O10 89.14(6) . .
O11 Fe1 O10 90.86(6) 5_666 .
O21 Fe1 O10 90.10(5) . .
O21 Fe1 O10 89.90(5) 5_666 .
O10 Fe1 O10 180.00(8) 5_666 .
C21 O11 Fe1 128.40(12) . .
C41 O21 Fe1 127.75(12) . .
C21 C11 H11A 109.5 . .
C21 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C21 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O11 C21 C31 124.82(17) . .
O11 C21 C11 115.60(18) . .
C31 C21 C11 119.58(18) . .
C21 C31 C41 125.63(17) . .
C21 C31 H31 117.2 . .
C41 C31 H31 117.2 . .
O21 C41 C31 125.20(16) . .
O21 C41 C51 115.59(16) . .
C31 C41 C51 119.20(16) . .
C41 C51 H51A 109.5 . .
C41 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C41 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C20 O10 C5A 110.5(4) . .
C20 O10 C5B 105.7(4) . .
C20 O10 Fe1 125.93(12) . .
C5A O10 Fe1 123.5(4) . .
C5B O10 Fe1 120.5(3) . .
O10 C20 C30 106.78(17) . .
O10 C20 H20A 110.4 . .
C30 C20 H20A 110.4 . .
O10 C20 H20B 110.4 . .
C30 C20 H20B 110.4 . .
H20A C20 H20B 108.6 . .
C20 C30 C40 105.15(19) . .
C20 C30 H30A 110.7 . .
C40 C30 H30A 110.7 . .
C20 C30 H30B 110.7 . .
C40 C30 H30B 110.7 . .
H30A C30 H30B 108.8 . .
C5A C40 C30 107.0(4) . .
C5B C40 C30 104.9(3) . .
C5B C40 H40C 110.8 . .
C30 C40 H40C 110.8 . .
C5B C40 H40D 110.8 . .
C30 C40 H40D 110.8 . .
H40C C40 H40D 108.8 . .
C5A C40 H40A 110.3 . .
C30 C40 H40A 110.3 . .
C5A C40 H40B 110.3 . .
C30 C40 H40B 110.3 . .
H40A C40 H40B 108.6 . .
O10 C5A C40 107.9(5) . .
O10 C5A H5AA 110.1 . .
C40 C5A H5AA 110.1 . .
O10 C5A H5AB 110.1 . .
C40 C5A H5AB 110.1 . .
H5AA C5A H5AB 108.4 . .
O10 C5B C40 104.3(5) . .
O10 C5B H5BA 110.9 . .
C40 C5B H5BA 110.9 . .
O10 C5B H5BB 110.9 . .
C40 C5B H5BB 110.9 . .
H5BA C5B H5BB 108.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O11 2.0142(13) .
Fe1 O11 2.0142(13) 5_666
Fe1 O21 2.0263(12) .
Fe1 O21 2.0263(12) 5_666
Fe1 O10 2.1763(14) 5_666
Fe1 O10 2.1764(14) .
O11 C21 1.253(2) .
O21 C41 1.248(2) .
C11 C21 1.495(2) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C21 C31 1.383(3) .
C31 C41 1.388(3) .
C31 H31 0.9500 .
C41 C51 1.493(3) .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
O10 C20 1.410(2) .
O10 C5A 1.415(8) .
O10 C5B 1.435(8) .
C20 C30 1.483(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C30 C40 1.484(3) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C40 C5A 1.422(10) .
C40 C5B 1.469(9) .
C40 H40C 0.9900 .
C40 H40D 0.9900 .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C5A H5AA 0.9900 .
C5A H5AB 0.9900 .
C5B H5BA 0.9900 .
C5B H5BB 0.9900 .
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
Fe1 O11 C21 C31 -1.4(3)
Fe1 O11 C21 C11 178.09(13)
O11 C21 C31 C41 -1.4(3)
C11 C21 C31 C41 179.1(2)
Fe1 O21 C41 C31 4.8(3)
Fe1 O21 C41 C51 -174.44(13)
C21 C31 C41 O21 -0.5(3)
C21 C31 C41 C51 178.76(19)
C5A O10 C20 C30 -1.6(4)
C5B O10 C20 C30 -29.8(4)
Fe1 O10 C20 C30 -178.61(16)
O10 C20 C30 C40 10.6(3)
C20 C30 C40 C5A -15.9(4)
C20 C30 C40 C5B 11.9(4)
C20 O10 C5A C40 -8.7(6)
Fe1 O10 C5A C40 168.5(3)
C30 C40 C5A O10 15.2(6)
C20 O10 C5B C40 37.3(5)
Fe1 O10 C5B C40 -171.8(3)
C30 C40 C5B O10 -29.8(5)
