#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/55/4065513.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_4065513
loop_
_publ_author_name
'Meyer, Steffen'
'Orben, Claudia Manuela'
'Demeshko, Serhiy'
'Dechert, Sebastian'
'Meyer, Franc'
_publ_section_title
;
 Synthesis and Characterization of Di- and Tetracarbene Iron(II) Complexes
 with Chelating N-Heterocyclic Carbene Ligands and Their Application in
 Aryl Grignard--Alkyl Halide Cross-Coupling
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              6692
_journal_paper_doi               10.1021/om200870w
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety
'(C22 H30 Fe N10 2+),(Br4 Fe 2-), 0.5(C4 H10 O), 0.5(C2 H3 N)'
_chemical_formula_sum            'C25 H36.5 Br4 Fe2 N10.5 O0.5'
_chemical_formula_weight         923.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 95.742(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0724(6)
_cell_length_b                   19.3867(7)
_cell_length_c                   13.9064(7)
_cell_measurement_reflns_used    23888
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      1.47
_cell_volume                     3506.6(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23888
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    5.420
_exptl_absorpt_correction_T_max  0.6881
_exptl_absorpt_correction_T_min  0.3493
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6808
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0207P)²+7.8290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                5443
_reflns_number_total             6808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200870w_si_002.cif
_cod_data_source_block           stm13-24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_original_formula_sum        'C25 H36.50 Br4 Fe2 N10.50 O0.50'
_cod_database_code               4065513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.25887(6) 0.49240(4) 0.74593(5) 0.02534(16) Uani 1 1 d . . .
N1 N 0.3608(3) 0.5962(2) 0.8734(3) 0.0287(9) Uani 1 1 d . . .
N2 N 0.4579(3) 0.5748(2) 0.7630(3) 0.0289(9) Uani 1 1 d . . .
N3 N 0.1792(3) 0.6029(2) 0.8619(3) 0.0387(11) Uani 1 1 d . . .
N4 N 0.0713(3) 0.5906(2) 0.7382(4) 0.0401(12) Uani 1 1 d . . .
N5 N 0.1422(3) 0.4326(2) 0.6993(3) 0.0294(10) Uani 1 1 d . . .
N6 N 0.2445(3) 0.4457(2) 0.8708(3) 0.0324(10) Uani 1 1 d . . .
N11 N 0.2781(3) 0.4840(2) 0.5390(3) 0.0284(9) Uani 1 1 d . . .
N12 N 0.2702(3) 0.5907(2) 0.5762(3) 0.0323(10) Uani 1 1 d . . .
N13 N 0.3634(3) 0.3931(2) 0.6283(3) 0.0266(9) Uani 1 1 d . . .
N14 N 0.4429(3) 0.3942(2) 0.7692(3) 0.0311(10) Uani 1 1 d . . .
C1 C 0.3671(4) 0.5546(3) 0.7950(3) 0.0281(11) Uani 1 1 d . . .
C2 C 0.5041(4) 0.6276(3) 0.8189(4) 0.0358(13) Uani 1 1 d . . .
H2 H 0.5659 0.6493 0.8102 0.080 Uiso 1 1 calc R . .
C3 C 0.4425(4) 0.6413(3) 0.8878(4) 0.0319(12) Uani 1 1 d . . .
H3 H 0.4528 0.6747 0.9358 0.080 Uiso 1 1 calc R . .
C4 C 0.2712(4) 0.5957(3) 0.9283(4) 0.0378(13) Uani 1 1 d . . .
H4A H 0.2688 0.5528 0.9638 0.080 Uiso 1 1 calc R . .
H4B H 0.2758 0.6335 0.9743 0.080 Uiso 1 1 calc R . .
C5 C 0.1612(4) 0.5647(3) 0.7803(4) 0.0325(12) Uani 1 1 d . . .
C6 C 0.1029(5) 0.6513(3) 0.8709(5) 0.0527(17) Uani 1 1 d . . .
H6 H 0.0996 0.6830 0.9207 0.080 Uiso 1 1 calc R . .
C7 C 0.0355(5) 0.6431(3) 0.7939(5) 0.0559(18) Uani 1 1 d . . .
H7 H -0.0249 0.6680 0.7798 0.080 Uiso 1 1 calc R . .
C8 C 0.0178(5) 0.5690(3) 0.6457(4) 0.0459(15) Uani 1 1 d . . .
H8A H 0.0647 0.5447 0.6090 0.080 Uiso 1 1 calc R . .
H8B H -0.0080 0.6089 0.6103 0.080 Uiso 1 1 calc R . .
H8C H -0.0384 0.5393 0.6571 0.080 Uiso 1 1 calc R . .
C9 C 0.5052(4) 0.5472(3) 0.6799(4) 0.0343(12) Uani 1 1 d . . .
H9A H 0.5576 0.5784 0.6629 0.080 Uiso 1 1 calc R . .
H9B H 0.4537 0.5422 0.6261 0.080 Uiso 1 1 calc R . .
H9C H 0.5354 0.5031 0.6963 0.080 Uiso 1 1 calc R . .
C11 C 0.2671(4) 0.5268(3) 0.6161(3) 0.0276(11) Uani 1 1 d . . .
C12 C 0.2800(5) 0.5868(3) 0.4780(4) 0.0426(14) Uani 1 1 d . . .
H12 H 0.2822 0.6239 0.4360 0.080 Uiso 1 1 calc R . .
C13 C 0.2858(4) 0.5201(3) 0.4544(4) 0.0378(13) Uani 1 1 d . . .
H13 H 0.2934 0.5018 0.3936 0.080 Uiso 1 1 calc R . .
C14 C 0.2892(4) 0.4095(3) 0.5469(3) 0.0298(12) Uani 1 1 d . . .
H14A H 0.2234 0.3887 0.5561 0.080 Uiso 1 1 calc R . .
H14B H 0.3123 0.3911 0.4880 0.080 Uiso 1 1 calc R . .
C15 C 0.3593(4) 0.4220(2) 0.7167(3) 0.0261(11) Uani 1 1 d . . .
C16 C 0.4455(4) 0.3492(3) 0.6253(4) 0.0370(13) Uani 1 1 d . . .
H16 H 0.4626 0.3240 0.5723 0.080 Uiso 1 1 calc R . .
C17 C 0.4961(4) 0.3500(3) 0.7140(4) 0.0388(13) Uani 1 1 d . . .
H17 H 0.5556 0.3255 0.7345 0.080 Uiso 1 1 calc R . .
C18 C 0.2671(5) 0.6566(3) 0.6260(4) 0.0425(14) Uani 1 1 d . . .
H18A H 0.2647 0.6487 0.6938 0.080 Uiso 1 1 calc R . .
H18B H 0.2071 0.6817 0.6008 0.080 Uiso 1 1 calc R . .
H18C H 0.3275 0.6827 0.6161 0.080 Uiso 1 1 calc R . .
C19 C 0.4793(5) 0.4101(3) 0.8700(4) 0.0420(14) Uani 1 1 d . . .
H19A H 0.4500 0.3779 0.9120 0.080 Uiso 1 1 calc R . .
H19B H 0.4589 0.4561 0.8851 0.080 Uiso 1 1 calc R . .
H19C H 0.5529 0.4067 0.8788 0.080 Uiso 1 1 calc R . .
C20 C 0.0727(4) 0.3984(3) 0.6769(4) 0.0302(12) Uani 1 1 d . . .
C21 C -0.0153(4) 0.3553(3) 0.6468(4) 0.0433(14) Uani 1 1 d . . .
H21A H -0.0259 0.3231 0.6972 0.080 Uiso 1 1 calc R . .
H21B H -0.0029 0.3307 0.5892 0.080 Uiso 1 1 calc R . .
H21C H -0.0753 0.3837 0.6340 0.080 Uiso 1 1 calc R . .
C22 C 0.2283(5) 0.4137(3) 0.9359(4) 0.0386(14) Uani 1 1 d . . .
C23 C 0.2070(6) 0.3724(4) 1.0195(4) 0.066(2) Uani 1 1 d . . .
H23A H 0.2654 0.3439 1.0393 0.080 Uiso 1 1 calc R . .
H23B H 0.1481 0.3437 1.0025 0.080 Uiso 1 1 calc R . .
H23C H 0.1934 0.4024 1.0716 0.080 Uiso 1 1 calc R . .
Fe2 Fe 0.72987(8) 0.7500 0.63879(7) 0.0304(2) Uani 1 2 d S . .
Br1 Br 0.76379(4) 0.63902(3) 0.71941(4) 0.03789(14) Uani 1 1 d . . .
Br2 Br 0.84733(7) 0.7500 0.50959(6) 0.0443(2) Uani 1 2 d S . .
Br3 Br 0.54119(6) 0.7500 0.60339(5) 0.03547(19) Uani 1 2 d S . .
Fe3 Fe 0.20053(11) 0.70532(7) 0.18102(9) 0.0267(3) Uani 0.50 1 d P A -1
Br4 Br 0.24719(7) 0.7510(4) 0.34226(6) 0.0317(3) Uani 0.50 1 d P A -1
Br5 Br 0.32853(7) 0.7571(6) 0.08067(6) 0.0241(12) Uani 0.50 1 d P A -1
Br6 Br 0.02840(8) 0.7576(9) 0.11277(7) 0.042(2) Uani 0.50 1 d P A -1
Br7 Br 0.22548(13) 0.58070(6) 0.19304(8) 0.0445(3) Uani 0.50 1 d P A -1
N7 N 0.3679(7) 0.2500 0.9313(7) 0.066(2) Uani 1 2 d S . .
C31 C 0.3208(8) 0.2500 0.8581(8) 0.052(2) Uani 1 2 d S . .
C32 C 0.2575(8) 0.2500 0.7654(7) 0.057(3) Uani 1 2 d S . .
H32A H 0.1977 0.2219 0.7701 0.080 Uiso 0.50 1 calc PR . .
H32B H 0.2965 0.2317 0.7163 0.080 Uiso 0.50 1 calc PR . .
H32C H 0.2366 0.2963 0.7489 0.080 Uiso 0.50 1 calc PR . .
O1 O 0.1261(8) 0.5256(6) 0.0873(7) 0.076(3) Uiso 0.50 1 d PD B -2
C41 C 0.2730(13) 0.5473(13) 0.1865(16) 0.116(8) Uiso 0.50 1 d PD B -2
H41A H 0.3039 0.5731 0.2408 0.080 Uiso 0.50 1 calc PR B -2
H41B H 0.3068 0.5582 0.1303 0.080 Uiso 0.50 1 calc PR B -2
H41C H 0.2799 0.4988 0.2000 0.080 Uiso 0.50 1 calc PR B -2
C42 C 0.1605(10) 0.5657(7) 0.1685(8) 0.045(3) Uiso 0.50 1 d PD B -2
H42A H 0.1240 0.5537 0.2236 0.080 Uiso 0.50 1 calc PR B -2
H42B H 0.1514 0.6145 0.1551 0.080 Uiso 0.50 1 calc PR B -2
C43 C 0.0184(12) 0.5256(11) 0.0681(12) 0.085(6) Uiso 0.50 1 d PD B -2
H43A H -0.0070 0.5727 0.0665 0.080 Uiso 0.50 1 calc PR B -2
H43B H -0.0121 0.5011 0.1189 0.080 Uiso 0.50 1 calc PR B -2
C44 C -0.0119(14) 0.4902(10) -0.0306(10) 0.069(5) Uiso 0.50 1 d PD B -2
H44A H -0.0854 0.4901 -0.0439 0.080 Uiso 0.50 1 calc PR B -2
H44B H 0.0130 0.4436 -0.0284 0.080 Uiso 0.50 1 calc PR B -2
H44C H 0.0179 0.5150 -0.0806 0.080 Uiso 0.50 1 calc PR B -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'
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'
Br Br -0.2901 2.4595 '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
C1 Fe1 C11 90.4(2) .
C1 Fe1 C15 91.5(2) .
C11 Fe1 C15 86.9(2) .
C1 Fe1 N5 176.4(2) .
C11 Fe1 N5 90.52(19) .
C15 Fe1 N5 91.99(19) .
C1 Fe1 N6 96.09(19) .
C11 Fe1 N6 172.54(19) .
C15 Fe1 N6 89.30(19) .
N5 Fe1 N6 83.22(17) .
C1 Fe1 C5 86.6(2) .
C11 Fe1 C5 94.5(2) .
C15 Fe1 C5 177.6(2) .
N5 Fe1 C5 89.94(19) .
N6 Fe1 C5 89.6(2) .
C1 N1 C3 112.4(4) .
C1 N1 C4 122.0(4) .
C3 N1 C4 125.3(4) .
C1 N2 C2 111.9(4) .
C1 N2 C9 127.0(4) .
C2 N2 C9 121.1(4) .
C5 N3 C6 112.3(5) .
C5 N3 C4 123.0(5) .
C6 N3 C4 124.6(5) .
C5 N4 C7 110.9(5) .
C5 N4 C8 126.2(5) .
C7 N4 C8 122.9(5) .
C20 N5 Fe1 176.4(4) .
C22 N6 Fe1 171.6(5) .
C11 N11 C13 112.5(4) .
C11 N11 C14 123.9(4) .
C13 N11 C14 123.5(4) .
C11 N12 C12 111.2(4) .
C11 N12 C18 127.0(4) .
C12 N12 C18 121.8(5) .
C15 N13 C16 112.6(4) .
C15 N13 C14 122.2(4) .
C16 N13 C14 125.1(4) .
C15 N14 C17 111.6(4) .
C15 N14 C19 126.5(4) .
C17 N14 C19 121.8(4) .
N2 C1 N1 102.5(4) .
N2 C1 Fe1 133.9(4) .
N1 C1 Fe1 123.4(4) .
C3 C2 N2 106.8(5) .
C2 C3 N1 106.5(5) .
N3 C4 N1 108.9(4) .
N4 C5 N3 103.2(5) .
N4 C5 Fe1 135.1(4) .
N3 C5 Fe1 121.7(4) .
C7 C6 N3 105.7(5) .
C6 C7 N4 107.8(5) .
N12 C11 N11 102.8(4) .
N12 C11 Fe1 134.5(4) .
N11 C11 Fe1 122.7(4) .
C13 C12 N12 107.9(5) .
C12 C13 N11 105.6(5) .
N13 C14 N11 109.3(4) .
N13 C15 N14 102.7(4) .
N13 C15 Fe1 124.2(4) .
N14 C15 Fe1 132.9(4) .
C17 C16 N13 106.3(4) .
C16 C17 N14 106.7(5) .
N5 C20 C21 179.0(6) .
N6 C22 C23 179.8(8) .
Br1 Fe2 Br1 123.19(5) 4_575
Br1 Fe2 Br3 102.90(3) 4_575
Br1 Fe2 Br3 102.90(3) .
Br1 Fe2 Br2 103.61(3) 4_575
Br1 Fe2 Br2 103.61(3) .
Br3 Fe2 Br2 122.36(5) .
Br4 Fe3 Br7 106.1(2) .
Br4 Fe3 Br5 104.42(18) .
Br7 Fe3 Br5 110.1(2) .
Br4 Fe3 Br6 109.1(2) .
Br7 Fe3 Br6 121.5(4) .
Br5 Fe3 Br6 104.3(2) .
N7 C31 C32 178.3(11) .
C43 O1 C42 112.6(11) .
O1 C42 C41 103.3(12) .
O1 C43 C44 109.3(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C1 1.931(5) .
Fe1 C11 1.938(5) .
Fe1 C15 1.965(5) .
Fe1 N5 1.972(5) .
Fe1 N6 1.983(4) .
Fe1 C5 1.986(5) .
N1 C1 1.366(6) .
N1 C3 1.380(6) .
N1 C4 1.460(6) .
N2 C1 1.365(6) .
N2 C2 1.387(7) .
N2 C9 1.465(6) .
N3 C5 1.356(7) .
N3 C6 1.384(7) .
N3 C4 1.448(7) .
N4 C5 1.356(7) .
N4 C7 1.388(7) .
N4 C8 1.462(7) .
N5 C20 1.143(6) .
N6 C22 1.135(7) .
N11 C11 1.373(6) .
N11 C13 1.381(6) .
N11 C14 1.456(6) .
N12 C11 1.360(6) .
N12 C12 1.386(7) .
N12 C18 1.455(7) .
N13 C15 1.356(6) .
N13 C16 1.375(6) .
N13 C14 1.450(6) .
N14 C15 1.363(6) .
N14 C17 1.384(7) .
N14 C19 1.468(6) .
C2 C3 1.337(7) .
C6 C7 1.327(9) .
C12 C13 1.338(8) .
C16 C17 1.340(7) .
C20 C21 1.449(7) .
C22 C23 1.461(8) .
Fe2 Br1 2.4460(7) 4_575
Fe2 Br1 2.4460(7) .
Fe2 Br3 2.4664(13) .
Fe2 Br2 2.4775(12) .
Fe3 Br4 2.431(3) .
Fe3 Br7 2.4414(18) .
Fe3 Br5 2.494(5) .
Fe3 Br6 2.562(7) .
N7 C31 1.137(12) .
C31 C32 1.460(14) .
O1 C43 1.407(15) .
O1 C42 1.407(13) .
C41 C42 1.510(16) .
C43 C44 1.551(16) .
