#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/59/4085931.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_4085931
loop_
_publ_author_name
'Bellow, James A.'
'Yousif, Maryam'
'Cabelof, Alyssa C.'
'Lord, Richard L.'
'Groysman, Stanislav'
_publ_section_title
;
 Reactivity Modes of an Iron Bis(alkoxide) Complex with Aryl Azides:
 Catalytic Nitrene Coupling vs Formation of Iron(III) Imido Dimers
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2917
_journal_paper_doi               10.1021/acs.organomet.5b00231
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C24 H29 Fe0.5 N O'
_chemical_formula_weight         375.41
_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                 110.977(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.3174(18)
_cell_length_b                   9.2385(7)
_cell_length_c                   21.1985(16)
_cell_measurement_temperature    100(2)
_cell_volume                     4263.9(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker Apex2'
_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  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47471
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SABABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubes
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.414
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     226
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0806
_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)+(0.0405P)²+44.3600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                3211
_reflns_number_total             3631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00231_si_002.cif
_cod_data_source_block           sg594_0m_compound_4
_cod_depositor_comments
'Adding full bibliography for 4085929--4085933.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C24 H29 Fe0.50 N O'
_cod_database_code               4085931
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 0.0000 0.75958(9) 0.2500 0.0188(2) Uani 1 2 d SU
O1 O 0.07380(13) 0.6687(3) 0.26614(14) 0.0245(7) Uani 1 1 d U
N1 N -0.01150(16) 0.9811(4) 0.12730(17) 0.0231(8) Uani 1 1 d U
C1 C 0.1325(2) 0.6236(5) 0.3049(2) 0.0278(9) Uani 1 1 d U
C2 C 0.1611(2) 0.5594(6) 0.2522(2) 0.0377(11) Uani 1 1 d U
C3 C 0.1287(4) 0.4221(8) 0.2190(4) 0.085(2) Uani 1 1 d U
C4 C 0.1571(3) 0.6741(7) 0.1999(3) 0.0534(16) Uani 1 1 d U
H3 H 0.1817 0.7582 0.2220 0.080 Uiso 1 1 calc R
H1 H 0.1141 0.7034 0.1776 0.080 Uiso 1 1 calc R
H2 H 0.1728 0.6349 0.1663 0.080 Uiso 1 1 calc R
C5 C 0.2300(3) 0.5244(12) 0.2837(4) 0.107(3) Uani 1 1 d U
H5 H 0.2428 0.4705 0.2511 0.161 Uiso 1 1 calc R
H4 H 0.2378 0.4656 0.3244 0.161 Uiso 1 1 calc R
H6 H 0.2535 0.6147 0.2957 0.161 Uiso 1 1 calc R
C6 C 0.1250(2) 0.5158(6) 0.3611(2) 0.0355(11) Uani 1 1 d U
C7 C 0.0716(3) 0.4118(7) 0.3310(3) 0.0652(19) Uani 1 1 d U
H7 H 0.0795 0.3499 0.2974 0.098 Uiso 1 1 calc R
H8 H 0.0337 0.4669 0.3092 0.098 Uiso 1 1 calc R
H9 H 0.0671 0.3514 0.3669 0.098 Uiso 1 1 calc R
C8 C 0.1086(3) 0.6072(7) 0.4133(3) 0.0543(16) Uani 1 1 d U
H11 H 0.1420 0.6755 0.4352 0.082 Uiso 1 1 calc R
H10 H 0.1029 0.5432 0.4474 0.082 Uiso 1 1 calc R
H12 H 0.0706 0.6609 0.3903 0.082 Uiso 1 1 calc R
C9 C 0.1813(3) 0.4231(6) 0.4016(3) 0.0474(14) Uani 1 1 d U
H15 H 0.1951 0.3675 0.3704 0.071 Uiso 1 1 calc R
H14 H 0.1698 0.3564 0.4312 0.071 Uiso 1 1 calc R
H13 H 0.2145 0.4864 0.4292 0.071 Uiso 1 1 calc R
C10 C 0.1717(2) 0.7590(6) 0.3383(2) 0.0371(11) Uani 1 1 d U
C11 C 0.2294(3) 0.7549(10) 0.3894(3) 0.073(2) Uani 1 1 d U
H20 H 0.2474 0.6645 0.4072 0.088 Uiso 1 1 calc R
C12 C 0.2616(3) 0.8866(13) 0.4152(3) 0.093(3) Uani 1 1 d U
H19 H 0.3004 0.8825 0.4508 0.111 Uiso 1 1 calc R
C13 C 0.2386(4) 1.0129(11) 0.3906(4) 0.086(2) Uani 1 1 d U
H18 H 0.2608 1.0990 0.4082 0.103 Uiso 1 1 calc R
C14 C 0.1828(3) 1.0203(8) 0.3398(3) 0.0623(17) Uani 1 1 d U
H16 H 0.1663 1.1116 0.3214 0.075 Uiso 1 1 calc R
C15 C 0.1500(2) 0.8953(6) 0.3148(3) 0.0399(12) Uani 1 1 d U
H17 H 0.1109 0.9033 0.2800 0.048 Uiso 1 1 calc R
C16 C -0.00769(19) 0.9048(5) 0.1721(2) 0.0227(9) Uani 1 1 d U
C17 C -0.0132(2) 1.0823(5) 0.0768(2) 0.0237(9) Uani 1 1 d U
C18 C -0.0692(2) 1.1148(5) 0.0267(2) 0.0266(9) Uani 1 1 d U
C19 C -0.1275(2) 1.0384(6) 0.0222(2) 0.0396(12) Uani 1 1 d U
H22 H -0.1242 0.9355 0.0127 0.059 Uiso 1 1 calc R
H21 H -0.1622 1.0812 -0.0142 0.059 Uiso 1 1 calc R
H23 H -0.1341 1.0486 0.0651 0.059 Uiso 1 1 calc R
C20 C -0.0685(2) 1.2198(5) -0.0194(2) 0.0322(10) Uani 1 1 d U
H24 H -0.1058 1.2455 -0.0544 0.039 Uiso 1 1 calc R
C21 C -0.0146(2) 1.2885(5) -0.0157(2) 0.0357(11) Uani 1 1 d U
H25 H -0.0155 1.3618 -0.0474 0.043 Uiso 1 1 calc R
C22 C 0.0404(2) 1.2506(5) 0.0341(2) 0.0353(11) Uani 1 1 d U
H29 H 0.0772 1.2972 0.0358 0.042 Uiso 1 1 calc R
C23 C 0.0425(2) 1.1451(5) 0.0819(2) 0.0275(9) Uani 1 1 d U
C24 C 0.1015(2) 1.1003(6) 0.1355(2) 0.0369(11) Uani 1 1 d U
H28 H 0.1356 1.1548 0.1302 0.055 Uiso 1 1 calc R
H27 H 0.1081 0.9965 0.1313 0.055 Uiso 1 1 calc R
H26 H 0.0995 1.1201 0.1801 0.055 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'
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 125.50(19) 2 .
O1 Fe1 C16 104.55(14) 2 2
O1 Fe1 C16 109.76(15) . 2
O1 Fe1 C16 109.76(14) 2 .
O1 Fe1 C16 104.55(14) . .
C16 Fe1 C16 99.9(2) 2 .
C1 O1 Fe1 155.7(3) . .
C16 N1 C17 175.2(4) . .
O1 C1 C10 108.8(4) . .
O1 C1 C2 105.5(3) . .
C10 C1 C2 106.9(4) . .
O1 C1 C6 106.1(3) . .
C10 C1 C6 111.1(4) . .
C2 C1 C6 118.0(4) . .
C4 C2 C3 110.9(5) . .
C4 C2 C5 104.3(5) . .
C3 C2 C5 107.2(6) . .
C4 C2 C1 108.6(4) . .
C3 C2 C1 111.7(5) . .
C5 C2 C1 113.9(4) . .
C2 C4 H3 109.5 . .
C2 C4 H1 109.5 . .
H3 C4 H1 109.5 . .
C2 C4 H2 109.5 . .
H3 C4 H2 109.5 . .
H1 C4 H2 109.5 . .
C2 C5 H5 109.5 . .
C2 C5 H4 109.5 . .
H5 C5 H4 109.5 . .
C2 C5 H6 109.5 . .
H5 C5 H6 109.5 . .
H4 C5 H6 109.5 . .
C7 C6 C9 106.7(5) . .
C7 C6 C8 105.7(5) . .
C9 C6 C8 106.4(4) . .
C7 C6 C1 111.7(4) . .
C9 C6 C1 117.4(4) . .
C8 C6 C1 108.2(4) . .
C6 C7 H7 109.5 . .
C6 C7 H8 109.5 . .
H7 C7 H8 109.5 . .
C6 C7 H9 109.5 . .
H7 C7 H9 109.5 . .
H8 C7 H9 109.5 . .
C6 C8 H11 109.5 . .
C6 C8 H10 109.5 . .
H11 C8 H10 109.5 . .
C6 C8 H12 109.5 . .
H11 C8 H12 109.5 . .
H10 C8 H12 109.5 . .
C6 C9 H15 109.5 . .
C6 C9 H14 109.5 . .
H15 C9 H14 109.5 . .
C6 C9 H13 109.5 . .
H15 C9 H13 109.5 . .
H14 C9 H13 109.5 . .
C15 C10 C11 115.6(6) . .
C15 C10 C1 119.1(4) . .
C11 C10 C1 125.2(6) . .
C10 C11 C12 120.1(8) . .
C10 C11 H20 119.9 . .
C12 C11 H20 119.9 . .
C13 C12 C11 121.4(7) . .
C13 C12 H19 119.3 . .
C11 C12 H19 119.3 . .
C12 C13 C14 119.8(7) . .
C12 C13 H18 120.1 . .
C14 C13 H18 120.1 . .
C13 C14 C15 120.1(8) . .
C13 C14 H16 120.0 . .
C15 C14 H16 120.0 . .
C14 C15 C10 122.9(6) . .
C14 C15 H17 118.5 . .
C10 C15 H17 118.5 . .
N1 C16 Fe1 177.3(4) . .
C18 C17 C23 124.4(4) . .
C18 C17 N1 119.2(4) . .
C23 C17 N1 116.5(4) . .
C20 C18 C17 116.6(4) . .
C20 C18 C19 121.6(4) . .
C17 C18 C19 121.8(4) . .
C18 C19 H22 109.5 . .
C18 C19 H21 109.5 . .
H22 C19 H21 109.5 . .
C18 C19 H23 109.5 . .
H22 C19 H23 109.5 . .
H21 C19 H23 109.5 . .
C18 C20 C21 121.5(4) . .
C18 C20 H24 119.3 . .
C21 C20 H24 119.3 . .
C22 C21 C20 120.2(4) . .
C22 C21 H25 119.9 . .
C20 C21 H25 119.9 . .
C21 C22 C23 120.9(4) . .
C21 C22 H29 119.5 . .
C23 C22 H29 119.5 . .
C17 C23 C22 116.5(4) . .
C17 C23 C24 121.5(4) . .
C22 C23 C24 122.0(4) . .
C23 C24 H28 109.5 . .
C23 C24 H27 109.5 . .
H28 C24 H27 109.5 . .
C23 C24 H26 109.5 . .
H28 C24 H26 109.5 . .
H27 C24 H26 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O1 1.833(3) 2
Fe1 O1 1.833(3) .
Fe1 C16 2.085(4) 2
Fe1 C16 2.085(4) .
O1 C1 1.385(5) .
N1 C16 1.160(5) .
N1 C17 1.411(5) .
C1 C10 1.562(7) .
C1 C2 1.605(6) .
C1 C6 1.610(7) .
C2 C4 1.512(7) .
C2 C3 1.515(9) .
C2 C5 1.538(8) .
C4 H3 0.9800 .
C4 H1 0.9800 .
C4 H2 0.9800 .
C5 H5 0.9800 .
C5 H4 0.9800 .
C5 H6 0.9800 .
C6 C7 1.521(8) .
C6 C9 1.545(7) .
C6 C8 1.545(7) .
C7 H7 0.9800 .
C7 H8 0.9800 .
C7 H9 0.9800 .
C8 H11 0.9800 .
C8 H10 0.9800 .
C8 H12 0.9800 .
C9 H15 0.9800 .
C9 H14 0.9800 .
C9 H13 0.9800 .
C10 C15 1.381(8) .
C10 C11 1.393(8) .
C11 C12 1.432(12) .
C11 H20 0.9500 .
C12 C13 1.311(13) .
C12 H19 0.9500 .
C13 C14 1.363(11) .
C13 H18 0.9500 .
C14 C15 1.381(8) .
C14 H16 0.9500 .
C15 H17 0.9500 .
C17 C18 1.389(6) .
C17 C23 1.393(6) .
C18 C20 1.381(6) .
C18 C19 1.505(6) .
C19 H22 0.9800 .
C19 H21 0.9800 .
C19 H23 0.9800 .
C20 C21 1.384(7) .
C20 H24 0.9500 .
C21 C22 1.384(7) .
C21 H25 0.9500 .
C22 C23 1.393(6) .
C22 H29 0.9500 .
C23 C24 1.495(7) .
C24 H28 0.9800 .
C24 H27 0.9800 .
C24 H26 0.9800 .
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 C1 -108.5(7) 2
C16 Fe1 O1 C1 17.2(7) 2
C16 Fe1 O1 C1 123.6(7) .
Fe1 O1 C1 C10 -56.1(8) .
Fe1 O1 C1 C2 -170.5(6) .
Fe1 O1 C1 C6 63.6(8) .
O1 C1 C2 C4 55.3(5) .
C10 C1 C2 C4 -60.4(5) .
C6 C1 C2 C4 173.6(4) .
O1 C1 C2 C3 -67.3(6) .
C10 C1 C2 C3 177.0(5) .
C6 C1 C2 C3 51.0(6) .
O1 C1 C2 C5 171.0(6) .
C10 C1 C2 C5 55.4(7) .
C6 C1 C2 C5 -70.6(7) .
O1 C1 C6 C7 43.3(5) .
C10 C1 C6 C7 161.4(5) .
C2 C1 C6 C7 -74.6(6) .
O1 C1 C6 C9 167.1(4) .
C10 C1 C6 C9 -74.8(5) .
C2 C1 C6 C9 49.1(6) .
O1 C1 C6 C8 -72.6(5) .
C10 C1 C6 C8 45.5(5) .
C2 C1 C6 C8 169.4(4) .
O1 C1 C10 C15 -14.2(5) .
C2 C1 C10 C15 99.2(5) .
C6 C1 C10 C15 -130.8(4) .
O1 C1 C10 C11 168.5(5) .
C2 C1 C10 C11 -78.0(6) .
C6 C1 C10 C11 52.0(6) .
C15 C10 C11 C12 1.3(8) .
C1 C10 C11 C12 178.6(5) .
C10 C11 C12 C13 -1.6(11) .
C11 C12 C13 C14 0.4(12) .
C12 C13 C14 C15 1.0(10) .
C13 C14 C15 C10 -1.2(8) .
C11 C10 C15 C14 0.0(7) .
C1 C10 C15 C14 -177.5(4) .
C17 N1 C16 Fe1 -137(7) .
O1 Fe1 C16 N1 -85(8) 2
O1 Fe1 C16 N1 52(8) .
C16 Fe1 C16 N1 166(8) 2
C16 N1 C17 C18 -131(5) .
C16 N1 C17 C23 48(5) .
C23 C17 C18 C20 -2.0(6) .
N1 C17 C18 C20 176.9(4) .
C23 C17 C18 C19 177.2(4) .
N1 C17 C18 C19 -3.8(6) .
C17 C18 C20 C21 0.2(6) .
C19 C18 C20 C21 -179.1(4) .
C18 C20 C21 C22 1.3(7) .
C20 C21 C22 C23 -1.1(7) .
C18 C17 C23 C22 2.2(6) .
N1 C17 C23 C22 -176.8(4) .
C18 C17 C23 C24 -177.3(4) .
N1 C17 C23 C24 3.7(6) .
C21 C22 C23 C17 -0.6(7) .
C21 C22 C23 C24 178.9(5) .
