#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/23/4102361.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_4102361
loop_
_publ_author_name
'Almaz S. Jalilov'
'Gaoquan Li'
'Stephen F. Nelsen'
'Ilia A. Guzei'
'Qin Wu'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;
_publ_contact_author_email       iguzei@chem.wisc.edu
_publ_contact_author_fax         608-262-0381
_publ_contact_author_name
;
Guzei, Ilia A. 
;
_publ_contact_author_phone       608-263-4694
_publ_section_title
;
 Solution and Solid-State Studies of Doubly Trimethylene-Bridged
 Tetraalkyl p-Phenylenediamine Diradical Dication Conformations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6176
_journal_page_last               6182
_journal_paper_doi               10.1021/ja100322k
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C22 H32 F12 N4 Sb2'
_chemical_formula_sum            'C22 H32 F12 N4 Sb2'
_chemical_formula_weight         824.02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;
_cell_angle_alpha                109.500(5)
_cell_angle_beta                 100.439(5)
_cell_angle_gamma                104.66(5)
_cell_formula_units_Z            1
_cell_length_a                   6.5273(5)
_cell_length_b                   10.0768(8)
_cell_length_c                   11.99250(13)
_cell_measurement_reflns_used    7348
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.04
_cell_measurement_theta_min      4.09
_cell_volume                     688.1(3)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.80° ω and 0.8 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10796
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         73.04
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    16.518
_exptl_absorpt_correction_T_max  0.3590
_exptl_absorpt_correction_T_min  0.2208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0307
_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)+(0.0399P)²+0.9271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2443
_reflns_number_total             2566
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja100322k_si_005.cif
_cod_data_source_block           nelsen20
_cod_original_cell_volume        688.13(8)
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4102361
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Sb1 Sb 0.15251(5) 0.14948(3) 0.77959(3) 0.04043(11) Uani 1 1 d . . .
F1 F 0.2407(6) 0.0657(4) 0.8914(3) 0.0554(8) Uani 1 1 d . A 1
F2 F -0.0285(5) -0.0427(3) 0.6653(3) 0.0537(7) Uani 1 1 d . A 1
F3 F 0.3900(5) 0.1298(4) 0.7172(3) 0.0589(8) Uani 1 1 d . A 1
F4 F 0.0646(5) 0.2375(4) 0.6729(3) 0.0554(8) Uani 1 1 d . A 1
F5 F 0.3330(5) 0.3409(3) 0.8984(3) 0.0562(8) Uani 1 1 d . A 1
F6 F -0.0787(6) 0.1726(4) 0.8488(3) 0.0583(8) Uani 1 1 d . A 1
N1 N 0.5680(7) 0.2895(4) 0.2520(4) 0.0413(9) Uani 1 1 d . . .
N2 N 1.1423(7) 0.4340(5) 0.2347(4) 0.0417(9) Uani 1 1 d . . .
C1 C 0.7399(8) 0.5178(5) 0.4384(4) 0.0384(10) Uani 1 1 d . . .
H1 H 0.7619 0.5770 0.3916 0.046 Uiso 1 1 calc R . .
C2 C 0.8104(8) 0.5859(5) 0.5656(5) 0.0408(10) Uani 1 1 d . . .
H2 H 0.8783 0.6915 0.6046 0.049 Uiso 1 1 calc R . .
C3 C 0.7843(8) 0.5029(5) 0.6393(5) 0.0384(10) Uani 1 1 d . . .
C4 C 0.6727(8) 0.3454(5) 0.5777(5) 0.0419(11) Uani 1 1 d . . .
H4 H 0.6474 0.2872 0.6252 0.050 Uiso 1 1 calc R . .
C5 C 0.6017(8) 0.2771(5) 0.4521(5) 0.0410(10) Uani 1 1 d . . .
H5 H 0.5285 0.1718 0.4136 0.049 Uiso 1 1 calc R . .
C6 C 0.6349(7) 0.3602(5) 0.3761(5) 0.0386(10) Uani 1 1 d . . .
C7 C 0.4228(9) 0.1312(5) 0.1918(5) 0.0459(11) Uani 1 1 d . . .
H7B H 0.3151 0.1132 0.2370 0.069 Uiso 1 1 calc R . .
H7C H 0.5126 0.0667 0.1922 0.069 Uiso 1 1 calc R . .
H7A H 0.3444 0.1087 0.1063 0.069 Uiso 1 1 calc R . .
C8 C 0.6364(8) 0.3593(5) 0.1691(5) 0.0407(10) Uani 1 1 d . . .
H8B H 0.7319 0.4647 0.2190 0.049 Uiso 1 1 calc R . .
H8A H 0.5036 0.3592 0.1140 0.049 Uiso 1 1 calc R . .
C9 C 0.7620(8) 0.2785(6) 0.0906(4) 0.0413(10) Uani 1 1 d . . .
H9B H 0.7903 0.3243 0.0311 0.050 Uiso 1 1 calc R . .
H9A H 0.6660 0.1729 0.0421 0.050 Uiso 1 1 calc R . .
C10 C 0.9831(8) 0.2813(5) 0.1632(4) 0.0423(11) Uani 1 1 d . . .
H10A H 0.9555 0.2318 0.2204 0.051 Uiso 1 1 calc R . .
H10B H 1.0488 0.2233 0.1046 0.051 Uiso 1 1 calc R . .
C11 C 1.1987(9) 0.5183(6) 0.1601(5) 0.0462(11) Uani 1 1 d . . .
H11B H 1.1784 0.4487 0.0759 0.069 Uiso 1 1 calc R . .
H11C H 1.3534 0.5845 0.1966 0.069 Uiso 1 1 calc R . .
H11A H 1.1023 0.5783 0.1576 0.069 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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_publ_flag
F3 Sb1 F4 91.11(16) . yes
F3 Sb1 F2 91.18(15) . yes
F4 Sb1 F2 92.29(14) . yes
F3 Sb1 F6 177.71(16) . yes
F4 Sb1 F6 90.42(15) . yes
F2 Sb1 F6 90.46(15) . yes
F3 Sb1 F5 89.74(16) . yes
F4 Sb1 F5 89.16(15) . yes
F2 Sb1 F5 178.26(15) . yes
F6 Sb1 F5 88.57(15) . yes
F3 Sb1 F1 90.04(15) . yes
F4 Sb1 F1 178.21(14) . yes
F2 Sb1 F1 89.05(15) . yes
F6 Sb1 F1 88.39(15) . yes
F5 Sb1 F1 89.47(14) . yes
C6 N1 C8 123.8(4) . ?
C6 N1 C7 120.2(4) . ?
C8 N1 C7 116.0(4) . ?
C3 N2 C11 122.2(4) 2_766 ?
C3 N2 C10 123.2(4) 2_766 ?
C11 N2 C10 114.3(4) . ?
C2 C1 C6 121.0(5) . ?
C2 C1 H1 119.5 . ?
C6 C1 H1 119.5 . ?
C1 C2 C3 121.7(5) . ?
C1 C2 H2 119.1 . ?
C3 C2 H2 119.1 . ?
N2 C3 C2 123.4(4) 2_766 ?
N2 C3 C4 119.0(4) 2_766 ?
C2 C3 C4 117.6(5) . ?
C5 C4 C3 121.0(5) . ?
C5 C4 H4 119.5 . ?
C3 C4 H4 119.5 . ?
C4 C5 C6 121.6(5) . ?
C4 C5 H5 119.2 . ?
C6 C5 H5 119.2 . ?
N1 C6 C1 122.6(5) . ?
N1 C6 C5 120.5(4) . ?
C1 C6 C5 116.9(4) . ?
N1 C7 H7B 109.5 . ?
N1 C7 H7C 109.5 . ?
H7B C7 H7C 109.5 . ?
N1 C7 H7A 109.5 . ?
H7B C7 H7A 109.5 . ?
H7C C7 H7A 109.5 . ?
N1 C8 C9 112.4(4) . ?
N1 C8 H8B 109.1 . ?
C9 C8 H8B 109.1 . ?
N1 C8 H8A 109.1 . ?
C9 C8 H8A 109.1 . ?
H8B C8 H8A 107.9 . ?
C8 C9 C10 115.2(4) . ?
C8 C9 H9B 108.5 . ?
C10 C9 H9B 108.5 . ?
C8 C9 H9A 108.5 . ?
C10 C9 H9A 108.5 . ?
H9B C9 H9A 107.5 . ?
N2 C10 C9 112.9(4) . ?
N2 C10 H10A 109.0 . ?
C9 C10 H10A 109.0 . ?
N2 C10 H10B 109.0 . ?
C9 C10 H10B 109.0 . ?
H10A C10 H10B 107.8 . ?
N2 C11 H11B 109.5 . ?
N2 C11 H11C 109.5 . ?
H11B C11 H11C 109.5 . ?
N2 C11 H11A 109.5 . ?
H11B C11 H11A 109.5 . ?
H11C C11 H11A 109.5 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 F3 1.865(3) . yes
Sb1 F4 1.871(3) . yes
Sb1 F2 1.873(3) . yes
Sb1 F6 1.877(3) . yes
Sb1 F5 1.883(3) . yes
Sb1 F1 1.888(3) . yes
N1 C6 1.347(6) . ?
N1 C8 1.466(6) . ?
N1 C7 1.477(6) . ?
N2 C3 1.364(6) 2_766 ?
N2 C11 1.458(7) . ?
N2 C10 1.473(6) . ?
C1 C2 1.377(6) . ?
C1 C6 1.421(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.409(7) . ?
C2 H2 0.9500 . ?
C3 N2 1.364(6) 2_766 ?
C3 C4 1.426(7) . ?
C4 C5 1.361(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.438(7) . ?
C5 H5 0.9500 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
C8 C9 1.526(6) . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.533(7) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11A 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
C6 C1 C2 C3 0.8(7) . .
C1 C2 C3 N2 178.0(4) . 2_766
C1 C2 C3 C4 -2.8(7) . .
N2 C3 C4 C5 -178.3(4) 2_766 .
C2 C3 C4 C5 2.5(7) . .
C3 C4 C5 C6 -0.3(7) . .
C8 N1 C6 C1 13.7(7) . .
C7 N1 C6 C1 -168.3(4) . .
C8 N1 C6 C5 -166.3(4) . .
C7 N1 C6 C5 11.7(6) . .
C2 C1 C6 N1 -178.6(4) . .
C2 C1 C6 C5 1.4(7) . .
C4 C5 C6 N1 178.4(4) . .
C4 C5 C6 C1 -1.7(7) . .
C6 N1 C8 C9 119.0(5) . .
C7 N1 C8 C9 -59.1(5) . .
N1 C8 C9 C10 -63.8(6) . .
C3 N2 C10 C9 114.8(5) 2_766 .
C11 N2 C10 C9 -59.4(5) . .
C8 C9 C10 N2 -60.7(6) . .
