#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:03:50 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179031 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/29/4122965.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_4122965
loop_
_publ_author_name
'Grubel, Katarzyna'
'Brennessel, William W.'
'Mercado, Brandon Q.'
'Holland, Patrick L.'
_publ_section_title
;
 Alkali Metal Control over N-N Cleavage in Iron Complexes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141120101403003
_journal_paper_doi               10.1021/ja507442b
_journal_year                    2014
_chemical_formula_moiety         'C44 H54 Cl2 Fe2 N4'
_chemical_formula_sum            'C44 H54 Cl2 Fe2 N4'
_chemical_formula_weight         821.51
_chemical_name_common            holmc22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 115.854(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.577(2)
_cell_length_b                   13.577(2)
_cell_length_c                   13.373(2)
_cell_measurement_reflns_used    4092
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      29.64
_cell_measurement_theta_min      2.26
_cell_volume                     2055.0(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_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  0.1356
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52227
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_correction_T_min  0.8732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         6845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0494
_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)+(0.0338P)²+1.4474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                4350
_reflns_number_total             6845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja507442b_si_002.cif
_cod_data_source_block           holmc22
_cod_original_cell_volume        2055.1(6)
_cod_database_code               4122965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.41791(3) 0.04077(2) 0.37210(3) 0.01907(9) Uani 1 1 d .
Cl1 Cl 0.56800(5) 0.11074(4) 0.53295(5) 0.02639(14) Uani 1 1 d .
N11 N 0.25867(16) 0.09895(14) 0.29828(16) 0.0183(4) Uani 1 1 d .
N21 N 0.43770(17) 0.05223(14) 0.23391(16) 0.0196(4) Uani 1 1 d .
C11 C 0.0672(2) 0.14453(19) 0.1493(2) 0.0254(5) Uani 1 1 d .
H11A H 0.0612 0.1825 0.2090 0.038 Uiso 1 1 calc R
H11B H 0.0116 0.0893 0.1287 0.038 Uiso 1 1 calc R
H11C H 0.0482 0.1871 0.0846 0.038 Uiso 1 1 calc R
C21 C 0.1918(2) 0.10553(16) 0.18913(19) 0.0193(4) Uani 1 1 d .
C31 C 0.2318(2) 0.08103(17) 0.10904(19) 0.0205(5) Uani 1 1 d .
C41 C 0.3508(2) 0.06601(16) 0.13160(19) 0.0198(5) Uani 1 1 d .
C51 C 0.3829(2) 0.06780(19) 0.0342(2) 0.0261(5) Uani 1 1 d .
H51A H 0.4690 0.0702 0.0624 0.039 Uiso 1 1 calc R
H51B H 0.3479 0.1261 -0.0116 0.039 Uiso 1 1 calc R
H51C H 0.3525 0.0083 -0.0107 0.039 Uiso 1 1 calc R
C61 C 0.1423(2) 0.0835(2) -0.0122(2) 0.0330(6) Uani 1 1 d .
H61A H 0.0647 0.0636 -0.0185 0.050 Uiso 1 1 calc R
H61B H 0.1671 0.0381 -0.0550 0.050 Uiso 1 1 calc R
H61C H 0.1374 0.1505 -0.0412 0.050 Uiso 1 1 calc R
C12 C 0.2153(2) 0.13932(18) 0.37263(19) 0.0213(5) Uani 1 1 d .
C22 C 0.2411(2) 0.23793(18) 0.4061(2) 0.0245(5) Uani 1 1 d .
C32 C 0.1996(2) 0.2762(2) 0.4785(2) 0.0318(6) Uani 1 1 d .
H32A H 0.2178 0.3424 0.5033 0.038 Uiso 1 1 calc R
C42 C 0.1321(2) 0.2199(2) 0.5154(2) 0.0363(7) Uani 1 1 d .
H42A H 0.1031 0.2477 0.5639 0.044 Uiso 1 1 calc R
C52 C 0.1070(2) 0.1233(2) 0.4813(2) 0.0316(6) Uani 1 1 d .
H52A H 0.0600 0.0851 0.5064 0.038 Uiso 1 1 calc R
C62 C 0.1490(2) 0.08056(19) 0.4109(2) 0.0246(5) Uani 1 1 d .
C72 C 0.3076(2) 0.30115(19) 0.3607(2) 0.0305(6) Uani 1 1 d .
H72A H 0.3068 0.3696 0.3836 0.046 Uiso 1 1 calc R
H72B H 0.2701 0.2971 0.2794 0.046 Uiso 1 1 calc R
H72C H 0.3894 0.2780 0.3895 0.046 Uiso 1 1 calc R
C82 C 0.1206(2) -0.02502(19) 0.3748(2) 0.0328(6) Uani 1 1 d .
H82A H 0.0723 -0.0533 0.4085 0.049 Uiso 1 1 calc R
H82B H 0.1942 -0.0626 0.3986 0.049 Uiso 1 1 calc R
H82C H 0.0770 -0.0279 0.2937 0.049 Uiso 1 1 calc R
C13 C 0.5586(2) 0.05574(18) 0.25043(19) 0.0218(5) Uani 1 1 d .
C23 C 0.6218(2) -0.03101(19) 0.2601(2) 0.0259(5) Uani 1 1 d .
C33 C 0.7377(2) -0.0232(2) 0.2743(2) 0.0320(6) Uani 1 1 d .
H33A H 0.7813 -0.0815 0.2784 0.038 Uiso 1 1 calc R
C43 C 0.7908(2) 0.0670(2) 0.2825(2) 0.0361(7) Uani 1 1 d .
H43A H 0.8702 0.0706 0.2923 0.043 Uiso 1 1 calc R
C53 C 0.7285(2) 0.1519(2) 0.2765(2) 0.0355(6) Uani 1 1 d .
H53A H 0.7663 0.2139 0.2843 0.043 Uiso 1 1 calc R
C63 C 0.6111(2) 0.14825(19) 0.2593(2) 0.0264(5) Uani 1 1 d .
C73 C 0.5661(3) -0.1300(2) 0.2528(2) 0.0341(6) Uani 1 1 d .
H73A H 0.6232 -0.1743 0.3081 0.051 Uiso 1 1 calc R
H73B H 0.5422 -0.1573 0.1783 0.051 Uiso 1 1 calc R
H73C H 0.4965 -0.1230 0.2673 0.051 Uiso 1 1 calc R
C83 C 0.5413(3) 0.24083(19) 0.2476(2) 0.0337(6) Uani 1 1 d .
H83A H 0.5934 0.2981 0.2619 0.051 Uiso 1 1 calc R
H83B H 0.5075 0.2399 0.3011 0.051 Uiso 1 1 calc R
H83C H 0.4776 0.2449 0.1720 0.051 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'
Cl Cl 0.1484 0.1585 '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_3
N11 Fe1 N21 90.85(8) .
N11 Fe1 Cl1 122.02(6) .
N21 Fe1 Cl1 116.40(6) .
N11 Fe1 Cl1 115.85(6) 3_656
N21 Fe1 Cl1 123.78(6) 3_656
Cl1 Fe1 Cl1 91.02(2) 3_656
Fe1 Cl1 Fe1 88.98(2) 3_656
C21 N11 C12 118.96(19) .
C21 N11 Fe1 126.43(16) .
C12 N11 Fe1 114.59(15) .
C41 N21 C13 119.26(19) .
C41 N21 Fe1 125.90(16) .
C13 N21 Fe1 114.51(14) .
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 .
N11 C21 C31 123.6(2) .
N11 C21 C11 118.1(2) .
C31 C21 C11 118.3(2) .
C41 C31 C21 124.8(2) .
C41 C31 C61 117.2(2) .
C21 C31 C61 117.5(2) .
N21 C41 C31 123.8(2) .
N21 C41 C51 118.2(2) .
C31 C41 C51 117.9(2) .
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 .
C31 C61 H61A 109.5 .
C31 C61 H61B 109.5 .
H61A C61 H61B 109.5 .
C31 C61 H61C 109.5 .
H61A C61 H61C 109.5 .
H61B C61 H61C 109.5 .
C62 C12 C22 121.2(2) .
C62 C12 N11 120.1(2) .
C22 C12 N11 118.7(2) .
C32 C22 C12 118.4(2) .
C32 C22 C72 121.0(2) .
C12 C22 C72 120.6(2) .
C42 C32 C22 121.2(3) .
C42 C32 H32A 119.4 .
C22 C32 H32A 119.4 .
C52 C42 C32 119.7(2) .
C52 C42 H42A 120.1 .
C32 C42 H42A 120.1 .
C42 C52 C62 121.3(3) .
C42 C52 H52A 119.3 .
C62 C52 H52A 119.3 .
C52 C62 C12 118.1(2) .
C52 C62 C82 120.5(2) .
C12 C62 C82 121.3(2) .
C22 C72 H72A 109.5 .
C22 C72 H72B 109.5 .
H72A C72 H72B 109.5 .
C22 C72 H72C 109.5 .
H72A C72 H72C 109.5 .
H72B C72 H72C 109.5 .
C62 C82 H82A 109.5 .
C62 C82 H82B 109.5 .
H82A C82 H82B 109.5 .
C62 C82 H82C 109.5 .
H82A C82 H82C 109.5 .
H82B C82 H82C 109.5 .
C23 C13 C63 121.4(2) .
C23 C13 N21 120.5(2) .
C63 C13 N21 118.1(2) .
C33 C23 C13 118.0(2) .
C33 C23 C73 120.6(2) .
C13 C23 C73 121.3(2) .
C43 C33 C23 121.5(3) .
C43 C33 H33A 119.3 .
C23 C33 H33A 119.3 .
C33 C43 C53 119.8(2) .
C33 C43 H43A 120.1 .
C53 C43 H43A 120.1 .
C43 C53 C63 121.0(3) .
C43 C53 H53A 119.5 .
C63 C53 H53A 119.5 .
C53 C63 C13 118.2(2) .
C53 C63 C83 121.1(2) .
C13 C63 C83 120.6(2) .
C23 C73 H73A 109.5 .
C23 C73 H73B 109.5 .
H73A C73 H73B 109.5 .
C23 C73 H73C 109.5 .
H73A C73 H73C 109.5 .
H73B C73 H73C 109.5 .
C63 C83 H83A 109.5 .
C63 C83 H83B 109.5 .
H83A C83 H83B 109.5 .
C63 C83 H83C 109.5 .
H83A C83 H83C 109.5 .
H83B C83 H83C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 N11 1.9711(19) .
Fe1 N21 1.9756(19) .
Fe1 Cl1 2.3561(7) .
Fe1 Cl1 2.3831(7) 3_656
Cl1 Fe1 2.3831(7) 3_656
N11 C21 1.332(3) .
N11 C12 1.435(3) .
N21 C41 1.341(3) .
N21 C13 1.438(3) .
C11 C21 1.513(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C21 C31 1.408(3) .
C31 C41 1.406(3) .
C31 C61 1.518(3) .
C41 C51 1.523(3) .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C61 H61A 0.9800 .
C61 H61B 0.9800 .
C61 H61C 0.9800 .
C12 C62 1.403(3) .
C12 C22 1.404(3) .
C22 C32 1.386(3) .
C22 C72 1.499(4) .
C32 C42 1.383(4) .
C32 H32A 0.9500 .
C42 C52 1.380(4) .
C42 H42A 0.9500 .
C52 C62 1.391(3) .
C52 H52A 0.9500 .
C62 C82 1.505(4) .
C72 H72A 0.9800 .
C72 H72B 0.9800 .
C72 H72C 0.9800 .
C82 H82A 0.9800 .
C82 H82B 0.9800 .
C82 H82C 0.9800 .
C13 C23 1.395(3) .
C13 C63 1.400(3) .
C23 C33 1.390(3) .
C23 C73 1.499(4) .
C33 C43 1.376(4) .
C33 H33A 0.9500 .
C43 C53 1.376(4) .
C43 H43A 0.9500 .
C53 C63 1.392(4) .
C53 H53A 0.9500 .
C63 C83 1.502(4) .
C73 H73A 0.9800 .
C73 H73B 0.9800 .
C73 H73C 0.9800 .
C83 H83A 0.9800 .
C83 H83B 0.9800 .
C83 H83C 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
_geom_torsion_site_symmetry_4
N11 Fe1 Cl1 Fe1 121.70(7) . 3_656
N21 Fe1 Cl1 Fe1 -129.03(6) . 3_656
Cl1 Fe1 Cl1 Fe1 0.0 3_656 3_656
N21 Fe1 N11 C21 18.71(19) . .
Cl1 Fe1 N11 C21 140.97(17) . .
Cl1 Fe1 N11 C21 -109.98(18) 3_656 .
N21 Fe1 N11 C12 -159.73(16) . .
Cl1 Fe1 N11 C12 -37.47(18) . .
Cl1 Fe1 N11 C12 71.58(16) 3_656 .
N11 Fe1 N21 C41 -17.14(19) . .
Cl1 Fe1 N21 C41 -143.97(17) . .
Cl1 Fe1 N21 C41 105.18(18) 3_656 .
N11 Fe1 N21 C13 156.19(16) . .
Cl1 Fe1 N21 C13 29.36(17) . .
Cl1 Fe1 N21 C13 -81.49(16) 3_656 .
C12 N11 C21 C31 170.9(2) . .
Fe1 N11 C21 C31 -7.5(3) . .
C12 N11 C21 C11 -7.1(3) . .
Fe1 N11 C21 C11 174.49(16) . .
N11 C21 C31 C41 -13.4(4) . .
C11 C21 C31 C41 164.6(2) . .
N11 C21 C31 C61 174.7(2) . .
C11 C21 C31 C61 -7.4(3) . .
C13 N21 C41 C31 -168.6(2) . .
Fe1 N21 C41 C31 4.5(3) . .
C13 N21 C41 C51 10.0(3) . .
Fe1 N21 C41 C51 -176.94(16) . .
C21 C31 C41 N21 15.0(4) . .
C61 C31 C41 N21 -173.0(2) . .
C21 C31 C41 C51 -163.6(2) . .
C61 C31 C41 C51 8.4(3) . .
C21 N11 C12 C62 90.2(3) . .
Fe1 N11 C12 C62 -91.2(2) . .
C21 N11 C12 C22 -90.1(3) . .
Fe1 N11 C12 C22 88.5(2) . .
C62 C12 C22 C32 0.1(4) . .
N11 C12 C22 C32 -179.6(2) . .
C62 C12 C22 C72 -177.3(2) . .
N11 C12 C22 C72 3.0(3) . .
C12 C22 C32 C42 -1.4(4) . .
C72 C22 C32 C42 176.0(2) . .
C22 C32 C42 C52 1.1(4) . .
C32 C42 C52 C62 0.5(4) . .
C42 C52 C62 C12 -1.8(4) . .
C42 C52 C62 C82 180.0(2) . .
C22 C12 C62 C52 1.4(4) . .
N11 C12 C62 C52 -178.9(2) . .
C22 C12 C62 C82 179.7(2) . .
N11 C12 C62 C82 -0.6(3) . .
C41 N21 C13 C23 -100.9(3) . .
Fe1 N21 C13 C23 85.3(2) . .
C41 N21 C13 C63 80.7(3) . .
Fe1 N21 C13 C63 -93.1(2) . .
C63 C13 C23 C33 -2.6(4) . .
N21 C13 C23 C33 179.1(2) . .
C63 C13 C23 C73 178.8(2) . .
N21 C13 C23 C73 0.5(3) . .
C13 C23 C33 C43 2.2(4) . .
C73 C23 C33 C43 -179.2(3) . .
C23 C33 C43 C53 -0.1(4) . .
C33 C43 C53 C63 -1.7(4) . .
C43 C53 C63 C13 1.3(4) . .
C43 C53 C63 C83 -177.2(3) . .
C23 C13 C63 C53 0.9(4) . .
N21 C13 C63 C53 179.3(2) . .
C23 C13 C63 C83 179.4(2) . .
N21 C13 C63 C83 -2.2(3) . .
