#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104015.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_4104015
loop_
_publ_author_name
'Brenda A. Frazier'
'Peter T. Wolczanski'
'Emil B. Lobkovsky'
'Thomas R. Cundari'
_publ_section_title
;
 Unusual Electronic Features and Reactivity of the Dipyridylazaallyl
 Ligand: Characterizations of (smif)2M [M = Fe, Co, Co+, Ni; smif =
 {(2-py)CH}2N] and [(TMS)2NFe]2(smif)2
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3428
_journal_page_last               3429
_journal_paper_doi               10.1021/ja8089747
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C24 H20 Fe N6'
_chemical_formula_sum            'C24 H20 Fe N6'
_chemical_formula_weight         448.31
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.809(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7442(4)
_cell_length_b                   27.4138(14)
_cell_length_c                   9.2149(4)
_cell_measurement_reflns_used    4857
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.53
_cell_volume                     2020.93(17)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25212
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.8610
_exptl_absorpt_correction_T_min  0.7229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.9777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                3994
_reflns_number_total             5007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8089747_si_001.cif
_cod_data_source_block           bf9
_cod_original_cell_volume        2020.93(16)
_cod_database_code               4104015
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
Fe1 Fe 0.85868(3) 0.129701(8) 0.16453(3) 0.02162(6) Uani 1 1 d
N1 N 0.90386(16) 0.18867(5) 0.06722(16) 0.0258(3) Uani 1 1 d
N2 N 0.90055(17) 0.17308(5) 0.33725(16) 0.0271(3) Uani 1 1 d
N3 N 0.83163(16) 0.08236(5) 0.31214(16) 0.0245(3) Uani 1 1 d
N4 N 0.61640(16) 0.13999(5) 0.05873(16) 0.0240(3) Uani 1 1 d
N5 N 0.81594(16) 0.08712(5) -0.01055(15) 0.0238(3) Uani 1 1 d
N6 N 1.08881(16) 0.10652(5) 0.22474(16) 0.0244(3) Uani 1 1 d
C1 C 0.9026(2) 0.19400(7) -0.0771(2) 0.0308(4) Uani 1 1 d
H1 H 0.867(2) 0.1660(7) -0.143(2) 0.029(5) Uiso 1 1 d
C2 C 0.9441(2) 0.23714(7) -0.1287(2) 0.0384(5) Uani 1 1 d
H2 H 0.947(2) 0.2373(7) -0.219(2) 0.041(6) Uiso 1 1 d
C3 C 0.9875(2) 0.27660(7) -0.0285(3) 0.0429(5) Uani 1 1 d
H3 H 1.015(3) 0.3056(8) -0.064(2) 0.054(7) Uiso 1 1 d
C4 C 0.9867(3) 0.27248(7) 0.1181(3) 0.0407(5) Uani 1 1 d
H4 H 1.016(2) 0.2971(8) 0.191(2) 0.043(6) Uiso 1 1 d
C5 C 0.9444(2) 0.22792(6) 0.1678(2) 0.0317(4) Uani 1 1 d
C6 C 0.9401(2) 0.21865(7) 0.3167(2) 0.0356(5) Uani 1 1 d
H6 H 0.960(2) 0.2417(8) 0.395(2) 0.043(6) Uiso 1 1 d
C7 C 0.8863(2) 0.15385(7) 0.4641(2) 0.0318(4) Uani 1 1 d
H7 H 0.902(2) 0.1747(7) 0.553(2) 0.032(5) Uiso 1 1 d
C8 C 0.8508(2) 0.10355(7) 0.45376(19) 0.0283(4) Uani 1 1 d
C9 C 0.8355(2) 0.07507(8) 0.5729(2) 0.0356(5) Uani 1 1 d
H9 H 0.848(2) 0.0914(7) 0.669(2) 0.038(6) Uiso 1 1 d
C10 C 0.8073(2) 0.02594(8) 0.5510(2) 0.0388(5) Uani 1 1 d
H10 H 0.798(2) 0.0038(8) 0.630(2) 0.046(6) Uiso 1 1 d
C11 C 0.7924(2) 0.00477(7) 0.4097(2) 0.0373(5) Uani 1 1 d
H11 H 0.776(2) -0.0296(8) 0.388(2) 0.045(6) Uiso 1 1 d
C12 C 0.8045(2) 0.03426(7) 0.2939(2) 0.0299(4) Uani 1 1 d
H12 H 0.7905(19) 0.0230(6) 0.192(2) 0.020(4) Uiso 1 1 d
C13 C 0.5199(2) 0.16813(6) 0.1051(2) 0.0283(4) Uani 1 1 d
H13 H 0.5809(19) 0.1862(6) 0.199(2) 0.021(4) Uiso 1 1 d
C14 C 0.3496(2) 0.17239(7) 0.0202(2) 0.0352(4) Uani 1 1 d
H14 H 0.292(3) 0.1913(8) 0.056(2) 0.048(6) Uiso 1 1 d
C15 C 0.2769(2) 0.14729(8) -0.1209(2) 0.0388(5) Uani 1 1 d
H15 H 0.165(3) 0.1497(8) -0.175(2) 0.049(6) Uiso 1 1 d
C16 C 0.3735(2) 0.11834(7) -0.1706(2) 0.0364(5) Uani 1 1 d
H16 H 0.329(2) 0.1019(8) -0.262(2) 0.042(6) Uiso 1 1 d
C17 C 0.5448(2) 0.11394(6) -0.0791(2) 0.0274(4) Uani 1 1 d
C18 C 0.6580(2) 0.08474(7) -0.1156(2) 0.0284(4) Uani 1 1 d
H18 H 0.625(2) 0.0651(7) -0.204(2) 0.033(5) Uiso 1 1 d
C19 C 0.9495(2) 0.06387(6) -0.0124(2) 0.0270(4) Uani 1 1 d
H19 H 0.943(2) 0.0419(7) -0.092(2) 0.032(5) Uiso 1 1 d
C20 C 1.1014(2) 0.07417(6) 0.1170(2) 0.0261(4) Uani 1 1 d
C21 C 1.2575(2) 0.05386(7) 0.1419(2) 0.0327(4) Uani 1 1 d
H21 H 1.262(2) 0.0328(7) 0.068(2) 0.035(5) Uiso 1 1 d
C22 C 1.3941(2) 0.06554(7) 0.2762(2) 0.0375(5) Uani 1 1 d
H22 H 1.496(2) 0.0511(7) 0.292(2) 0.040(6) Uiso 1 1 d
C23 C 1.3787(2) 0.09702(7) 0.3859(2) 0.0375(5) Uani 1 1 d
H23 H 1.469(2) 0.1062(7) 0.478(2) 0.033(5) Uiso 1 1 d
C24 C 1.2242(2) 0.11714(7) 0.3543(2) 0.0307(4) Uani 1 1 d
H24 H 1.205(2) 0.1406(7) 0.422(2) 0.025(5) 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'
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
N2 Fe1 N5 179.11(6)
N2 Fe1 N3 82.51(6)
N5 Fe1 N3 98.32(6)
N2 Fe1 N4 97.50(6)
N5 Fe1 N4 82.17(6)
N3 Fe1 N4 91.80(6)
N2 Fe1 N6 97.87(6)
N5 Fe1 N6 82.48(6)
N3 Fe1 N6 89.23(6)
N4 Fe1 N6 164.61(6)
N2 Fe1 N1 82.02(6)
N5 Fe1 N1 97.16(6)
N3 Fe1 N1 164.45(6)
N4 Fe1 N1 91.76(6)
N6 Fe1 N1 91.34(6)
C1 N1 C5 118.96(15)
C1 N1 Fe1 128.56(12)
C5 N1 Fe1 112.47(12)
C6 N2 C7 128.16(16)
C6 N2 Fe1 116.21(13)
C7 N2 Fe1 115.62(12)
C12 N3 C8 118.86(15)
C12 N3 Fe1 129.02(12)
C8 N3 Fe1 112.07(11)
C13 N4 C17 119.14(14)
C13 N4 Fe1 128.29(11)
C17 N4 Fe1 112.57(11)
C18 N5 C19 128.55(15)
C18 N5 Fe1 115.98(12)
C19 N5 Fe1 115.47(11)
C24 N6 C20 119.33(15)
C24 N6 Fe1 128.42(13)
C20 N6 Fe1 112.22(10)
N1 C1 C2 122.78(17)
C3 C2 C1 119.00(19)
C4 C3 C2 119.47(19)
C3 C4 C5 120.28(19)
N1 C5 C4 119.48(18)
N1 C5 C6 114.53(16)
C4 C5 C6 125.98(17)
N2 C6 C5 114.73(16)
N2 C7 C8 115.08(16)
N3 C8 C9 119.74(17)
N3 C8 C7 114.64(15)
C9 C8 C7 125.61(17)
C10 C9 C8 120.16(18)
C9 C10 C11 119.63(19)
C12 C11 C10 118.42(19)
N3 C12 C11 123.14(18)
N4 C13 C14 123.03(16)
C15 C14 C13 118.26(18)
C16 C15 C14 119.64(17)
C15 C16 C17 120.34(17)
N4 C17 C16 119.54(17)
N4 C17 C18 114.44(14)
C16 C17 C18 126.01(16)
N5 C18 C17 114.83(15)
N5 C19 C20 115.04(15)
N6 C20 C21 119.74(15)
N6 C20 C19 114.79(14)
C21 C20 C19 125.47(16)
C22 C21 C20 119.46(18)
C21 C22 C23 120.17(17)
C24 C23 C22 118.32(17)
N6 C24 C23 122.93(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N2 1.9002(14)
Fe1 N5 1.9022(14)
Fe1 N3 1.9623(14)
Fe1 N4 1.9623(13)
Fe1 N6 1.9645(13)
Fe1 N1 1.9644(14)
N1 C1 1.333(2)
N1 C5 1.370(2)
N2 C6 1.330(2)
N2 C7 1.333(2)
N3 C12 1.338(2)
N3 C8 1.375(2)
N4 C13 1.335(2)
N4 C17 1.369(2)
N5 C18 1.330(2)
N5 C19 1.337(2)
N6 C24 1.330(2)
N6 C20 1.368(2)
C1 C2 1.377(3)
C2 C3 1.372(3)
C3 C4 1.359(3)
C4 C5 1.406(3)
C5 C6 1.411(3)
C7 C8 1.408(3)
C8 C9 1.397(3)
C9 C10 1.369(3)
C10 C11 1.383(3)
C11 C12 1.376(3)
C13 C14 1.379(2)
C14 C15 1.379(3)
C15 C16 1.366(3)
C16 C17 1.396(2)
C17 C18 1.415(3)
C19 C20 1.410(2)
C20 C21 1.404(2)
C21 C22 1.367(3)
C22 C23 1.377(3)
C23 C24 1.377(3)
