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#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/41/4324100.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_4324100
loop_
_publ_author_name
'Julia B. H. Strautmann'
'Carl-Georg Freiherr von Richthofen'
'Gabriele Heinze-Brückner'
'Serena DeBeer'
'Eberhard Bothe'
'Eckhard Bill'
'Thomas Weyhermüller'
'Anja Stammler'
'Hartmut Bögge'
'Thorsten Glaser'
_publ_contact_author_address
;     Fakultät f. Chemie
      Universität Bielefeld
      33501 Bielefeld
      Germany
;
_publ_contact_author_email       thorsten.glaser@uni-bielefeld.de
_publ_contact_author_fax         '49 521 106 6003'
_publ_contact_author_name        'Prof. Dr. T. Glaser'
_publ_contact_author_phone       '49 521 106 6105'
_publ_section_title
;
 Molecular and Electronic Structures of Dinuclear Iron Complexes
 Incorporating Strongly Electron-Donating Ligands: Implications for the
 Generation of the One- and Two-Electron Oxidized Forms
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              155
_journal_page_last               171
_journal_paper_doi               10.1021/ic101535y
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C22 H32 N2 O2'
_chemical_formula_weight         356.50
_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                 113.6210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1065(6)
_cell_length_b                   9.6850(3)
_cell_length_c                   13.2882(5)
_cell_measurement_reflns_used    6426
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.46
_cell_volume                     2017.09(12)
_computing_cell_refinement       'SAINT (Bruker AXS, 2001)'
_computing_data_collection       'SMART (Bruker AXS, 2001)'
_computing_data_reduction        'SAINT (Bruker AXS, 2001)'
_computing_molecular_graphics    'DIAMOND 2.1 (Crystal Impact, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS SMART 1K'
_diffrn_measurement_method       omega-scan
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10047
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Bruker AXS, 2001)'
_exptl_crystal_colour            violet-colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0374
_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)+(0.0680P)²+0.8321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                1945
_reflns_number_total             2179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101535y_si_002_1.cif
_cod_data_source_block           gl1523
_cod_database_code               4324100
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47277(5) 0.62415(8) 0.10623(6) 0.0357(2) Uani 1 1 d . . .
H1O H 0.4737(12) 0.540(2) 0.1359(15) 0.076(5) Uiso 1 1 d . . .
N1 N 0.42541(5) 0.37171(8) 0.14605(6) 0.0269(2) Uani 1 1 d . . .
C1 C 0.36432(7) 0.75656(10) -0.02844(8) 0.0330(2) Uani 1 1 d . . .
C2 C 0.28582(7) 0.76121(12) -0.11727(9) 0.0371(3) Uani 1 1 d . . .
H2A H 0.2658(10) 0.8498(16) -0.1507(13) 0.058(4) Uiso 1 1 d . . .
C3 C 0.23655(7) 0.64384(12) -0.15967(9) 0.0370(3) Uani 1 1 d . . .
C4 C 0.26915(7) 0.51767(11) -0.11086(8) 0.0336(3) Uani 1 1 d . . .
H4A H 0.2352(8) 0.4329(14) -0.1385(10) 0.039(3) Uiso 1 1 d . . .
C5 C 0.34835(6) 0.50735(10) -0.02285(8) 0.0286(2) Uani 1 1 d . . .
C6 C 0.39524(6) 0.62802(10) 0.01855(8) 0.0290(2) Uani 1 1 d . . .
C7 C 0.15123(9) 0.65351(19) -0.25591(11) 0.0542(4) Uani 1 1 d . . .
H7A H 0.1185(12) 0.567(2) -0.2697(15) 0.079(6) Uiso 1 1 d . . .
H7B H 0.1567(14) 0.673(2) -0.3251(19) 0.104(7) Uiso 1 1 d . . .
H7C H 0.1142(13) 0.716(2) -0.2433(16) 0.090(6) Uiso 1 1 d . . .
C8 C 0.41544(10) 0.88510(12) 0.01842(12) 0.0460(3) Uani 1 1 d . . .
H8A H 0.3856(13) 0.966(2) -0.0150(16) 0.088(6) Uiso 1 1 d . . .
H8B H 0.4688(14) 0.888(2) 0.0085(17) 0.089(6) Uiso 1 1 d . . .
H8C H 0.4283(13) 0.8982(19) 0.0982(18) 0.088(6) Uiso 1 1 d . . .
C9 C 0.38516(7) 0.36876(10) 0.02477(8) 0.0300(2) Uani 1 1 d . . .
H9A H 0.3377(8) 0.2973(14) -0.0037(10) 0.041(3) Uiso 1 1 d . . .
H9B H 0.4296(8) 0.3431(13) 0.0000(10) 0.036(3) Uiso 1 1 d . . .
C10 C 0.36086(7) 0.39120(12) 0.19112(9) 0.0363(3) Uani 1 1 d . . .
H10A H 0.3255(9) 0.4732(15) 0.1576(11) 0.050(4) Uiso 1 1 d . . .
H10B H 0.3875(9) 0.4032(14) 0.2706(12) 0.044(3) Uiso 1 1 d . . .
H10C H 0.3202(9) 0.3110(16) 0.1743(12) 0.053(4) Uiso 1 1 d . . .
C11 C 0.47533(7) 0.24566(10) 0.18779(8) 0.0317(2) Uani 1 1 d . . .
H11A H 0.5149(8) 0.2353(12) 0.1512(10) 0.031(3) Uiso 1 1 d . . .
H11B H 0.4373(8) 0.1643(14) 0.1658(10) 0.040(3) Uiso 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'
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
C6 O1 H1O 103.7(11) . . ?
C10 N1 C11 111.92(8) . . ?
C10 N1 C9 110.51(8) . . ?
C11 N1 C9 110.06(7) . . ?
C2 C1 C6 118.19(10) . . ?
C2 C1 C8 121.90(10) . . ?
C6 C1 C8 119.90(10) . . ?
C1 C2 C3 122.67(10) . . ?
C1 C2 H2A 117.7(9) . . ?
C3 C2 H2A 119.6(9) . . ?
C4 C3 C2 117.64(10) . . ?
C4 C3 C7 121.36(12) . . ?
C2 C3 C7 121.00(11) . . ?
C3 C4 C5 121.83(10) . . ?
C3 C4 H4A 119.4(7) . . ?
C5 C4 H4A 118.8(7) . . ?
C4 C5 C6 118.76(9) . . ?
C4 C5 C9 121.15(9) . . ?
C6 C5 C9 120.04(9) . . ?
O1 C6 C1 117.90(9) . . ?
O1 C6 C5 121.21(9) . . ?
C1 C6 C5 120.89(10) . . ?
C3 C7 H7A 113.0(11) . . ?
C3 C7 H7B 112.6(13) . . ?
H7A C7 H7B 104.4(17) . . ?
C3 C7 H7C 112.4(12) . . ?
H7A C7 H7C 102.2(17) . . ?
H7B C7 H7C 111.6(18) . . ?
C1 C8 H8A 112.0(12) . . ?
C1 C8 H8B 112.8(11) . . ?
H8A C8 H8B 106.0(16) . . ?
C1 C8 H8C 112.8(11) . . ?
H8A C8 H8C 104.1(15) . . ?
H8B C8 H8C 108.7(16) . . ?
N1 C9 C5 111.96(8) . . ?
N1 C9 H9A 111.8(7) . . ?
C5 C9 H9A 108.2(7) . . ?
N1 C9 H9B 106.7(7) . . ?
C5 C9 H9B 109.6(8) . . ?
H9A C9 H9B 108.4(10) . . ?
N1 C10 H10A 110.1(8) . . ?
N1 C10 H10B 110.9(8) . . ?
H10A C10 H10B 109.1(11) . . ?
N1 C10 H10C 112.1(8) . . ?
H10A C10 H10C 106.0(12) . . ?
H10B C10 H10C 108.3(12) . . ?
N1 C11 C11 113.30(6) . 2_655 ?
N1 C11 H11A 108.1(7) . . ?
C11 C11 H11A 110.1(7) 2_655 . ?
N1 C11 H11B 109.7(7) . . ?
C11 C11 H11B 109.5(7) 2_655 . ?
H11A C11 H11B 105.9(10) . . ?
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
O1 C6 1.3710(12) . ?
O1 H1O 0.91(2) . ?
N1 C10 1.4641(13) . ?
N1 C11 1.4654(12) . ?
N1 C9 1.4775(12) . ?
C1 C2 1.3887(16) . ?
C1 C6 1.3981(14) . ?
C1 C8 1.5053(15) . ?
C2 C3 1.3926(17) . ?
C2 H2A 0.963(16) . ?
C3 C4 1.3910(15) . ?
C3 C7 1.5095(16) . ?
C4 C5 1.3942(14) . ?
C4 H4A 0.988(14) . ?
C5 C6 1.3993(13) . ?
C5 C9 1.5097(13) . ?
C7 H7A 0.98(2) . ?
C7 H7B 0.98(2) . ?
C7 H7C 0.94(2) . ?
C8 H8A 0.94(2) . ?
C8 H8B 0.97(2) . ?
C8 H8C 1.00(2) . ?
C9 H9A 1.017(13) . ?
C9 H9B 0.974(13) . ?
C10 H10A 0.990(14) . ?
C10 H10B 0.975(14) . ?
C10 H10C 1.006(15) . ?
C11 C11 1.5258(19) 2_655 ?
C11 H11A 0.984(13) . ?
C11 H11B 0.989(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5247940
