#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:22:53 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179374 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/71/4327131.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_4327131
loop_
_publ_author_name
'Yu He'
'John D. Gorden'
'Christian R. Goldsmith'
_publ_section_title
;
 Steric Modifications Tune the Regioselectivity of the Alkane Oxidation
 Catalyzed by Non-Heme Iron Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12651
_journal_page_last               12660
_journal_paper_doi               10.1021/ic201695a
_journal_volume                  50
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H36 N4'
_chemical_formula_sum            'C32 H36 N4'
_chemical_formula_weight         476.65
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2011-06-09T09:28:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.012(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1486(16)
_cell_length_b                   11.4474(11)
_cell_length_c                   14.5026(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     2691.7(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '0.3 wide w/ exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8963
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.08
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0896P)²+1.2111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2093
_reflns_number_gt                2343
_reflns_number_total             3312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic201695a_si_002_1.cif
_cod_data_source_block           bbpc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4327131
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
C1 C 0.4703(2) 0.8662(2) 0.0951(2) 0.0858(9) Uani 1 1 d .
H1A H 0.4976 0.9247 0.138 0.103 Uiso 1 1 calc R
C2 C 0.41883(18) 0.8963(3) 0.0047(2) 0.0756(8) Uani 1 1 d .
H2A H 0.4113 0.9742 -0.0143 0.091 Uiso 1 1 calc R
C3 C 0.37905(17) 0.8105(3) -0.0568(2) 0.0753(8) Uani 1 1 d .
H3A H 0.3431 0.8297 -0.1182 0.09 Uiso 1 1 calc R
C4 C 0.39106(14) 0.6958(2) -0.02958(18) 0.0613(6) Uani 1 1 d .
H4A H 0.3643 0.6375 -0.073 0.074 Uiso 1 1 calc R
C5 C 0.44220(12) 0.66684(19) 0.06113(15) 0.0456(5) Uani 1 1 d .
C6 C 0.45584(13) 0.54155(19) 0.09376(16) 0.0503(5) Uani 1 1 d .
H6A H 0.4295 0.4909 0.0388 0.06 Uiso 1 1 calc R
H6B H 0.5145 0.5249 0.1156 0.06 Uiso 1 1 calc R
C7 C 0.33242(13) 0.5227(2) 0.13804(17) 0.0550(6) Uani 1 1 d .
H8A H 0.3105 0.4578 0.0943 0.066 Uiso 1 1 calc R
H8B H 0.3156 0.5943 0.1011 0.066 Uiso 1 1 calc R
C8 C 0.29571(12) 0.52010(18) 0.21896(16) 0.0473(5) Uani 1 1 d .
C9 C 0.31610(13) 0.6038(2) 0.29003(17) 0.0551(6) Uani 1 1 d .
H9A H 0.3544 0.6612 0.2897 0.066 Uiso 1 1 calc R
C10 C 0.28011(17) 0.6033(3) 0.3622(2) 0.0729(8) Uani 1 1 d .
H10A H 0.2937 0.6608 0.4101 0.087 Uiso 1 1 calc R
C11 C 0.22427(16) 0.5182(3) 0.3633(2) 0.0788(9) Uani 1 1 d .
H11A H 0.2003 0.5167 0.4123 0.095 Uiso 1 1 calc R
C12 C 0.20452(16) 0.4367(3) 0.2923(2) 0.0804(9) Uani 1 1 d .
H12A H 0.166 0.3796 0.2924 0.096 Uiso 1 1 calc R
C13 C 0.23990(13) 0.4362(2) 0.22036(18) 0.0567(6) Uani 1 1 d .
H13 H 0.2259 0.3786 0.1725 0.068 Uiso 1 1 calc R
C14 C 0.45335(12) 0.40512(17) 0.22266(15) 0.0440(5) Uani 1 1 d .
H14A H 0.4262 0.3951 0.2721 0.053 Uiso 1 1 calc R
C15 C 0.43301(14) 0.29557(19) 0.15778(19) 0.0578(6) Uani 1 1 d .
H15A H 0.3746 0.295 0.1207 0.069 Uiso 1 1 calc R
H15B H 0.4634 0.2978 0.1119 0.069 Uiso 1 1 calc R
C16 C 0.45501(17) 0.1848(2) 0.2185(2) 0.0729(8) Uani 1 1 d .
H16A H 0.4206 0.1787 0.2597 0.088 Uiso 1 1 calc R
H16B H 0.4441 0.1175 0.1756 0.088 Uiso 1 1 calc R
N1 N 0.48271(17) 0.7523(2) 0.12415(18) 0.0819(7) Uani 1 1 d .
N2 N 0.42294(10) 0.51595(14) 0.17272(13) 0.0447(4) Uani 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 0 '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'
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
C2 C1 N1 121.7(3) . .
C2 C1 H1A 119.2 . .
N1 C1 H1A 119.2 . .
C3 C2 C1 118.6(3) . .
C3 C2 H2A 120.7 . .
C1 C2 H2A 120.7 . .
C2 C3 C4 120.7(2) . .
C2 C3 H3A 119.6 . .
C4 C3 H3A 119.6 . .
C5 C4 C3 120.1(3) . .
C5 C4 H4A 120 . .
C3 C4 H4A 120 . .
C4 C5 N1 120.0(2) . .
C4 C5 C6 121.4(2) . .
N1 C5 C6 118.67(19) . .
N2 C6 C5 112.17(17) . .
N2 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
N2 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N2 C7 C8 113.35(17) . .
N2 C7 H8A 108.9 . .
C8 C7 H8A 108.9 . .
N2 C7 H8B 108.9 . .
C8 C7 H8B 108.9 . .
H8A C7 H8B 107.7 . .
C13 C8 C9 119.5(2) . .
C13 C8 C7 120.1(2) . .
C9 C8 C7 120.4(2) . .
C8 C9 C10 120.2(2) . .
C8 C9 H9A 119.9 . .
C10 C9 H9A 119.9 . .
C11 C10 C9 120.0(3) . .
C11 C10 H10A 120 . .
C9 C10 H10A 120 . .
C12 C11 C10 119.1(3) . .
C12 C11 H11A 120.4 . .
C10 C11 H11A 120.4 . .
C11 C12 C13 121.5(3) . .
C11 C12 H12A 119.3 . .
C13 C12 H12A 119.3 . .
C8 C13 C12 119.8(3) . .
C8 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
N2 C14 C14 113.39(11) . 2_655
N2 C14 C15 115.40(17) . .
C14 C14 C15 107.83(15) 2_655 .
N2 C14 H14A 106.5 . .
C14 C14 H14A 106.5 2_655 .
C15 C14 H14A 106.5 . .
C16 C15 C14 111.2(2) . .
C16 C15 H15A 109.4 . .
C14 C15 H15A 109.4 . .
C16 C15 H15B 109.4 . .
C14 C15 H15B 109.4 . .
H15A C15 H15B 108 . .
C16 C16 C15 111.19(18) 2_655 .
C16 C16 H16A 109.4 2_655 .
C15 C16 H16A 109.4 . .
C16 C16 H16B 109.4 2_655 .
C15 C16 H16B 109.4 . .
H16A C16 H16B 108 . .
C5 N1 C1 118.9(2) . .
C6 N2 C14 113.18(16) . .
C6 N2 C7 110.83(17) . .
C14 N2 C7 112.33(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.365(4) .
C1 N1 1.365(4) .
C1 H1A 0.93 .
C2 C3 1.352(4) .
C2 H2A 0.93 .
C3 C4 1.367(4) .
C3 H3A 0.93 .
C4 C5 1.363(3) .
C4 H4A 0.93 .
C5 N1 1.364(3) .
C5 C6 1.505(3) .
C6 N2 1.462(3) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C7 N2 1.470(3) .
C7 C8 1.502(3) .
C7 H8A 0.97 .
C7 H8B 0.97 .
C8 C13 1.361(3) .
C8 C9 1.367(3) .
C9 C10 1.377(3) .
C9 H9A 0.93 .
C10 C11 1.370(4) .
C10 H10A 0.93 .
C11 C12 1.347(4) .
C11 H11A 0.93 .
C12 C13 1.368(4) .
C12 H12A 0.93 .
C13 H13 0.93 .
C14 N2 1.470(3) .
C14 C14 1.537(4) 2_655
C14 C15 1.538(3) .
C14 H14A 0.98 .
C15 C16 1.519(3) .
C15 H15A 0.97 .
C15 H15B 0.97 .
C16 C16 1.516(6) 2_655
C16 H16A 0.97 .
C16 H16B 0.97 .
