#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:50:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178965 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/94/4119401.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_4119401
loop_
_publ_author_name
'Erika R. Bartholomew'
'Emily C. Volpe'
'Peter T. Wolczanski'
'Emil B. Lobkovsky'
'Thomas R. Cundari'
_publ_section_title
;
 Selective Extraction of N2 from Air by Diarylimine Iron Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3511
_journal_page_last               3527
_journal_paper_doi               10.1021/ja311021u
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C20 H23 F6 Fe N3 P2'
_chemical_formula_sum            'C20 H23 F6 Fe N3 P2'
_chemical_formula_weight         537.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 121.8450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0597(7)
_cell_length_b                   9.1733(4)
_cell_length_c                   15.7972(10)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.87
_cell_measurement_theta_min      2.55
_cell_volume                     2346.2(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9138
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.8845
_exptl_absorpt_correction_T_min  0.8176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                4493
_reflns_number_total             5119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311021u_si_001_1.cif
_cod_data_source_block           ev10
_cod_database_code               4119401
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'
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 0.167193(17) 0.82040(3) 0.293100(19) 0.02250(6) Uani 1 1 d .
F1 F 0.00134(8) 0.58853(18) 0.14792(10) 0.0441(4) Uani 1 1 d .
F2 F -0.06811(8) 0.40678(17) 0.21218(11) 0.0453(4) Uani 1 1 d .
F3 F 0.10937(10) 0.5636(2) 0.54248(11) 0.0635(5) Uani 1 1 d .
F4 F 0.43883(8) 1.28567(16) 0.41433(11) 0.0437(4) Uani 1 1 d .
F5 F 0.34534(8) 1.21317(16) 0.21934(10) 0.0391(4) Uani 1 1 d .
F6 F 0.22751(8) 1.01180(17) 0.15569(9) 0.0382(4) Uani 1 1 d .
N1 N 0.21960(11) 0.8345(2) 0.43622(13) 0.0274(5) Uani 1 1 d .
N2 N 0.11501(12) 0.8061(2) 0.15879(14) 0.0292(5) Uani 1 1 d .
N3 N 0.08204(14) 0.7971(3) 0.07686(16) 0.0498(7) Uani 1 1 d .
C1 C 0.09715(13) 0.6777(2) 0.31126(17) 0.0266(5) Uani 1 1 d .
C2 C 0.03175(12) 0.5872(3) 0.24712(17) 0.0297(5) Uani 1 1 d .
C3 C -0.00516(13) 0.4915(3) 0.27974(18) 0.0325(6) Uani 1 1 d .
C4 C 0.01917(14) 0.4794(3) 0.37906(19) 0.0363(6) Uani 1 1 d .
H4 H -0.0175(12) 0.406(2) 0.3903(16) 0.019(6) Uiso 1 1 d .
C5 C 0.08235(14) 0.5683(3) 0.44319(17) 0.0358(6) Uani 1 1 d .
C6 C 0.12228(13) 0.6635(3) 0.41323(17) 0.0298(6) Uani 1 1 d .
C7 C 0.19109(15) 0.7551(3) 0.48032(17) 0.0344(6) Uani 1 1 d .
H7 H 0.2172(15) 0.762(3) 0.555(2) 0.050(8) Uiso 1 1 d .
C8 C 0.28976(15) 0.9322(3) 0.49279(17) 0.0362(6) Uani 1 1 d .
H8B H 0.3407(13) 0.870(3) 0.5427(16) 0.023(6) Uiso 1 1 d .
H8A H 0.2827(16) 1.000(3) 0.538(2) 0.050(8) Uiso 1 1 d .
C9 C 0.30522(13) 1.0083(2) 0.42003(16) 0.0280(5) Uani 1 1 d .
C10 C 0.36760(14) 1.1129(3) 0.45441(17) 0.0315(6) Uani 1 1 d .
H10 H 0.4011(13) 1.141(3) 0.5296(16) 0.026(6) Uiso 1 1 d .
C11 C 0.37993(13) 1.1811(3) 0.38557(18) 0.0304(6) Uani 1 1 d .
C12 C 0.33305(13) 1.1454(3) 0.28630(17) 0.0283(5) Uani 1 1 d .
C13 C 0.27162(13) 1.0403(3) 0.25577(16) 0.0268(5) Uani 1 1 d .
C14 C 0.25365(12) 0.9698(2) 0.31856(16) 0.0238(5) Uani 1 1 d .
P1 P 0.25428(4) 0.64532(8) 0.30839(5) 0.04028(19) Uani 1 1 d D
C15 C 0.21659(19) 0.4610(3) 0.2916(3) 0.0619(10) Uani 1 1 d D
H15A H 0.2596 0.3934 0.2999 0.093 Uiso 1 1 calc R
H15B H 0.1676 0.4501 0.2245 0.093 Uiso 1 1 calc R
H15C H 0.2020 0.4391 0.3411 0.093 Uiso 1 1 calc R
C16 C 0.3528(2) 0.6382(5) 0.4218(4) 0.118(2) Uani 1 1 d D
H16A H 0.3848 0.5567 0.4190 0.177 Uiso 1 1 calc R
H16B H 0.3452 0.6242 0.4779 0.177 Uiso 1 1 calc R
H16C H 0.3824 0.7297 0.4306 0.177 Uiso 1 1 calc R
C17 C 0.2839(2) 0.6528(4) 0.2144(3) 0.0828(10) Uani 1 1 d D
H17A H 0.3221 0.5728 0.2261 0.124 Uiso 1 1 calc R
H17B H 0.3109 0.7462 0.2198 0.124 Uiso 1 1 calc R
H17C H 0.2344 0.6434 0.1476 0.124 Uiso 1 1 calc R
P2 P 0.08113(3) 1.00352(7) 0.26990(5) 0.03247(15) Uani 1 1 d D
C18 C 0.07044(19) 1.1420(3) 0.1830(3) 0.0646(9) Uani 1 1 d D
H18A H 0.0318 1.2169 0.1780 0.097 Uiso 1 1 calc R
H18B H 0.0493 1.0979 0.1173 0.097 Uiso 1 1 calc R
H18C H 0.1244 1.1865 0.2063 0.097 Uiso 1 1 calc R
C19 C -0.02580(17) 0.9554(4) 0.2188(4) 0.0977(15) Uani 1 1 d D
H19A H -0.0576 1.0434 0.2119 0.147 Uiso 1 1 calc R
H19B H -0.0298 0.8865 0.2635 0.147 Uiso 1 1 calc R
H19C H -0.0481 0.9102 0.1532 0.147 Uiso 1 1 calc R
C20 C 0.1068(3) 1.1119(5) 0.3772(3) 0.1149(16) Uani 1 1 d D
H20A H 0.0650 1.1882 0.3581 0.172 Uiso 1 1 calc R
H20B H 0.1610 1.1570 0.4034 0.172 Uiso 1 1 calc R
H20C H 0.1082 1.0497 0.4285 0.172 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 N1 178.17(10)
N2 Fe1 C1 97.20(9)
N1 Fe1 C1 81.25(9)
N2 Fe1 C14 99.73(9)
N1 Fe1 C14 81.82(9)
C1 Fe1 C14 163.06(9)
N2 Fe1 P1 89.54(7)
N1 Fe1 P1 91.47(6)
C1 Fe1 P1 91.62(7)
C14 Fe1 P1 89.13(7)
N2 Fe1 P2 87.74(7)
N1 Fe1 P2 91.32(6)
C1 Fe1 P2 91.59(7)
C14 Fe1 P2 88.49(6)
P1 Fe1 P2 176.04(3)
C7 N1 C8 121.3(2)
C7 N1 Fe1 118.81(15)
C8 N1 Fe1 119.86(16)
N3 N2 Fe1 178.9(2)
C2 C1 C6 114.0(2)
C2 C1 Fe1 134.17(19)
C6 C1 Fe1 111.81(15)
F1 C2 C3 116.44(19)
F1 C2 C1 120.6(2)
C3 C2 C1 122.9(2)
F2 C3 C2 119.0(2)
F2 C3 C4 118.3(2)
C2 C3 C4 122.7(2)
C5 C4 C3 115.5(2)
C4 C5 F3 118.9(2)
C4 C5 C6 123.3(2)
F3 C5 C6 117.7(2)
C5 C6 C1 121.5(2)
C5 C6 C7 124.2(2)
C1 C6 C7 114.2(2)
N1 C7 C6 113.9(2)
N1 C8 C9 107.67(19)
C10 C9 C14 123.6(2)
C10 C9 C8 119.5(2)
C14 C9 C8 116.9(2)
C11 C10 C9 118.0(2)
F4 C11 C12 118.3(2)
F4 C11 C10 120.7(2)
C12 C11 C10 120.9(2)
F5 C12 C11 120.5(2)
F5 C12 C13 120.6(2)
C11 C12 C13 118.8(2)
F6 C13 C14 120.70(19)
F6 C13 C12 115.1(2)
C14 C13 C12 124.2(2)
C13 C14 C9 114.4(2)
C13 C14 Fe1 131.84(16)
C9 C14 Fe1 113.73(18)
C16 P1 C15 103.89(18)
C16 P1 C17 101.7(2)
C15 P1 C17 100.57(18)
C16 P1 Fe1 117.63(15)
C15 P1 Fe1 116.37(11)
C17 P1 Fe1 114.33(12)
C20 P2 C18 101.18(19)
C20 P2 C19 103.8(2)
C18 P2 C19 100.63(17)
C20 P2 Fe1 116.74(12)
C18 P2 Fe1 115.60(12)
C19 P2 Fe1 116.49(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N2 1.811(2)
Fe1 N1 1.9347(19)
Fe1 C1 1.996(2)
Fe1 C14 2.014(2)
Fe1 P1 2.2292(7)
Fe1 P2 2.2389(7)
F1 C2 1.354(3)
F2 C3 1.353(3)
F3 C5 1.369(3)
F4 C11 1.360(3)
F5 C12 1.350(3)
F6 C13 1.368(2)
N1 C7 1.308(3)
N1 C8 1.459(3)
N2 N3 1.104(3)
C1 C2 1.391(3)
C1 C6 1.424(3)
C2 C3 1.384(3)
C3 C4 1.386(4)
C4 C5 1.362(3)
C5 C6 1.395(3)
C6 C7 1.443(3)
C8 C9 1.501(4)
C9 C10 1.396(3)
C9 C14 1.413(3)
C10 C11 1.378(4)
C11 C12 1.373(3)
C12 C13 1.392(3)
C13 C14 1.370(3)
P1 C16 1.786(3)
P1 C15 1.801(3)
P1 C17 1.847(4)
P2 C20 1.796(4)
P2 C18 1.802(3)
P2 C19 1.807(3)
