#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/23/4102358.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_4102358
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         'C16 H25 Cl8 N3 Sb'
_chemical_formula_sum            'C16 H25 Cl8 N3 Sb'
_chemical_formula_weight         664.74
_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                72.189(7)
_cell_angle_beta                 89.358(10)
_cell_angle_gamma                88.158(7)
_cell_formula_units_Z            2
_cell_length_a                   9.6088(9)
_cell_length_b                   9.6875(8)
_cell_length_c                   14.5497(16)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.43
_cell_measurement_theta_min      3.19
_cell_volume                     1288.8(2)
_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 0.949
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5 ° 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7631
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         69.43
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    16.200
_exptl_absorpt_correction_T_max  0.3968
_exptl_absorpt_correction_T_min  0.1321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             658
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.434
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         7653
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0814
_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)+(0.1734P)²+0.9085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2183
_refine_ls_wR_factor_ref         0.2288
_reflns_number_gt                6507
_reflns_number_total             7653
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja100322k_si_002.cif
_cod_data_source_block           nelsen17
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4102358
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
Sb1 Sb 0.0000 0.5000 0.5000 0.0530(2) Uani 1 2 d SU
Cl1 Cl 0.1483(2) 0.4810(3) 0.37321(18) 0.0715(6) Uani 1 1 d U
Cl2 Cl 0.1685(2) 0.6356(2) 0.55077(14) 0.0609(5) Uani 1 1 d U
Cl3 Cl 0.0997(3) 0.2852(2) 0.60392(19) 0.0742(6) Uani 1 1 d U
Sb2 Sb 0.0000 0.0000 1.0000 0.0559(2) Uani 1 2 d SU
Cl4 Cl -0.0795(3) 0.1759(2) 0.85810(16) 0.0732(6) Uani 1 1 d U
Cl5 Cl -0.0017(3) -0.1804(3) 0.92084(18) 0.0763(6) Uani 1 1 d U
Cl6 Cl 0.2332(3) 0.0496(3) 0.95227(18) 0.0806(7) Uani 1 1 d U
N1 N 0.2866(8) 0.0861(8) 0.3309(5) 0.0667(18) Uani 1 1 d U
N2 N 0.5032(7) 0.1240(10) 0.6744(6) 0.0682(18) Uani 1 1 d U
C1 C 0.3347(9) 0.1035(8) 0.4132(6) 0.0588(18) Uani 1 1 d U
C2 C 0.4291(9) 0.2101(10) 0.4168(6) 0.063(2) Uani 1 1 d U
H2 H 0.4591 0.2769 0.3580 0.076 Uiso 1 1 calc R
C3 C 0.4780(9) 0.2208(11) 0.4996(7) 0.067(2) Uani 1 1 d U
H3 H 0.5377 0.2978 0.4980 0.080 Uiso 1 1 calc R
C4 C 0.4440(9) 0.1216(10) 0.5895(7) 0.0619(19) Uani 1 1 d U
C5 C 0.3452(10) 0.0178(10) 0.5883(7) 0.065(2) Uani 1 1 d U
H5 H 0.3169 -0.0498 0.6473 0.077 Uiso 1 1 calc R
C6 C 0.2896(10) 0.0130(10) 0.5037(7) 0.070(2) Uani 1 1 d U
H6 H 0.2183 -0.0534 0.5056 0.084 Uiso 1 1 calc R
C7 C 0.1583(10) 0.0077(10) 0.3311(6) 0.065(2) Uani 1 1 d U
H7B H 0.1632 -0.0861 0.3833 0.078 Uiso 1 1 calc R
H7A H 0.1500 -0.0131 0.2689 0.078 Uiso 1 1 calc R
C8 C 0.0317(11) 0.0942(11) 0.3459(8) 0.075(2) Uani 1 1 d U
H8A H 0.0281 0.1882 0.2954 0.089 Uiso 1 1 calc R
H8B H 0.0369 0.1096 0.4093 0.089 Uiso 1 1 calc R
H8C H -0.0523 0.0411 0.3427 0.089 Uiso 1 1 calc R
C9 C 0.3381(14) 0.1683(12) 0.2354(7) 0.096(3) Uani 1 1 d U
H9B H 0.4087 0.2366 0.2423 0.115 Uiso 1 1 calc R
H9A H 0.2602 0.2256 0.1964 0.115 Uiso 1 1 calc R
C10 C 0.4036(15) 0.0647(16) 0.1828(7) 0.103(4) Uani 1 1 d U
H10A H 0.3314 -0.0021 0.1760 0.124 Uiso 1 1 calc R
H10B H 0.4310 0.1233 0.1170 0.124 Uiso 1 1 calc R
C11 C 0.5803(10) 0.2529(13) 0.6776(7) 0.077(2) Uani 1 1 d U
H11B H 0.6300 0.2295 0.7400 0.092 Uiso 1 1 calc R
H11A H 0.6510 0.2753 0.6255 0.092 Uiso 1 1 calc R
C12 C 0.4896(12) 0.3817(15) 0.6665(10) 0.092(3) Uani 1 1 d U
H12A H 0.4416 0.4069 0.6042 0.110 Uiso 1 1 calc R
H12B H 0.5458 0.4630 0.6692 0.110 Uiso 1 1 calc R
H12C H 0.4207 0.3612 0.7188 0.110 Uiso 1 1 calc R
C13 C 0.4716(13) 0.0243(15) 0.7687(8) 0.095(4) Uani 1 1 d U
H13B H 0.3988 -0.0417 0.7616 0.114 Uiso 1 1 calc R
H13A H 0.4335 0.0802 0.8105 0.114 Uiso 1 1 calc R
C14 C 0.3426(17) 0.6560(18) 0.0137(10) 0.112(4) Uani 1 1 d U
H14A H 0.2720 0.7346 0.0089 0.134 Uiso 1 1 calc R
H14B H 0.3764 0.6675 -0.0526 0.134 Uiso 1 1 calc R
Cl7 Cl 0.4817(5) 0.6888(7) 0.0783(3) 0.1517(19) Uani 1 1 d U
Cl8 Cl 0.2575(7) 0.4957(5) 0.0511(3) 0.1455(17) Uani 1 1 d U
N3 N 0.6861(10) 0.3144(10) 0.2264(6) 0.078(2) Uani 1 1 d U
C15 C 0.7603(11) 0.4046(10) 0.2069(6) 0.068(2) Uani 1 1 d U
C16 C 0.8617(13) 0.5229(13) 0.1816(8) 0.087(3) Uani 1 1 d U
H16A H 0.9396 0.4967 0.1456 0.104 Uiso 1 1 calc R
H16B H 0.8968 0.5375 0.2409 0.104 Uiso 1 1 calc R
H16C H 0.8157 0.6127 0.1418 0.104 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'
Cl Cl 0.3639 0.7018 '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'
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
_geom_angle_publ_flag
Cl3 Sb1 Cl3 180.00(12) 2_566 . yes
Cl3 Sb1 Cl1 89.49(10) 2_566 . yes
Cl3 Sb1 Cl1 90.51(10) . . yes
Cl3 Sb1 Cl1 90.51(10) 2_566 2_566 yes
Cl3 Sb1 Cl1 89.49(10) . 2_566 yes
Cl1 Sb1 Cl1 180.000(1) . 2_566 yes
Cl3 Sb1 Cl2 90.41(7) 2_566 . yes
Cl3 Sb1 Cl2 89.59(7) . . yes
Cl1 Sb1 Cl2 90.51(7) . . yes
Cl1 Sb1 Cl2 89.49(7) 2_566 . yes
Cl3 Sb1 Cl2 89.59(7) 2_566 2_566 yes
Cl3 Sb1 Cl2 90.41(7) . 2_566 yes
Cl1 Sb1 Cl2 89.49(7) . 2_566 yes
Cl1 Sb1 Cl2 90.51(7) 2_566 2_566 yes
Cl2 Sb1 Cl2 180.0 . 2_566 yes
Cl4 Sb2 Cl4 180.00(8) 2_557 . yes
Cl4 Sb2 Cl6 90.61(9) 2_557 2_557 yes
Cl4 Sb2 Cl6 89.39(9) . 2_557 yes
Cl4 Sb2 Cl6 89.39(9) 2_557 . yes
Cl4 Sb2 Cl6 90.61(9) . . yes
Cl6 Sb2 Cl6 180.000(1) 2_557 . yes
Cl4 Sb2 Cl5 89.68(8) 2_557 . yes
Cl4 Sb2 Cl5 90.32(8) . . yes
Cl6 Sb2 Cl5 89.69(10) 2_557 . yes
Cl6 Sb2 Cl5 90.31(10) . . yes
Cl4 Sb2 Cl5 90.32(8) 2_557 2_557 yes
Cl4 Sb2 Cl5 89.68(8) . 2_557 yes
Cl6 Sb2 Cl5 90.31(10) 2_557 2_557 yes
Cl6 Sb2 Cl5 89.69(10) . 2_557 yes
Cl5 Sb2 Cl5 180.000(1) . 2_557 yes
C1 N1 C9 122.8(7) . . ?
C1 N1 C7 120.6(8) . . ?
C9 N1 C7 115.3(7) . . ?
C4 N2 C13 124.6(7) . . ?
C4 N2 C11 119.9(9) . . ?
C13 N2 C11 114.1(7) . . ?
N1 C1 C2 124.3(8) . . ?
N1 C1 C6 120.3(7) . . ?
C2 C1 C6 115.4(7) . . ?
C3 C2 C1 122.5(9) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 122.1(8) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N2 C4 C3 122.5(7) . . ?
N2 C4 C5 121.1(9) . . ?
C3 C4 C5 116.4(8) . . ?
C6 C5 C4 120.9(9) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 122.2(8) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N1 C7 C8 111.4(7) . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
H7B C7 H7A 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 110.7(9) . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
H9B C9 H9A 108.1 . . ?
C13 C10 C9 115.5(8) 2_656 . ?
C13 C10 H10A 108.4 2_656 . ?
C9 C10 H10A 108.4 . . ?
C13 C10 H10B 108.4 2_656 . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 N2 113.0(8) . . ?
C12 C11 H11B 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N2 C11 H11A 109.0 . . ?
H11B C11 H11A 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C10 113.0(9) . 2_656 ?
N2 C13 H13B 109.0 . . ?
C10 C13 H13B 109.0 2_656 . ?
N2 C13 H13A 109.0 . . ?
C10 C13 H13A 109.0 2_656 . ?
H13B C13 H13A 107.8 . . ?
Cl8 C14 Cl7 121.3(9) . . ?
Cl8 C14 H14A 107.0 . . ?
Cl7 C14 H14A 107.0 . . ?
Cl8 C14 H14B 107.0 . . ?
Cl7 C14 H14B 107.0 . . ?
H14A C14 H14B 106.7 . . ?
N3 C15 C16 178.8(12) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 Cl3 2.348(2) 2_566 yes
Sb1 Cl3 2.348(2) . yes
Sb1 Cl1 2.366(2) . yes
Sb1 Cl1 2.366(2) 2_566 yes
Sb1 Cl2 2.3771(17) . yes
Sb1 Cl2 2.3771(17) 2_566 yes
Sb2 Cl4 2.355(2) 2_557 yes
Sb2 Cl4 2.355(2) . yes
Sb2 Cl6 2.359(2) 2_557 yes
Sb2 Cl6 2.359(2) . yes
Sb2 Cl5 2.370(2) . yes
Sb2 Cl5 2.370(2) 2_557 yes
N1 C1 1.347(10) . ?
N1 C9 1.464(13) . ?
N1 C7 1.469(11) . ?
N2 C4 1.372(11) . ?
N2 C13 1.452(14) . ?
N2 C11 1.486(11) . ?
C1 C2 1.410(11) . ?
C1 C6 1.412(13) . ?
C2 C3 1.332(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(11) . ?
C5 C6 1.361(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.506(15) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.55(2) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C13 1.50(2) 2_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.467(18) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C10 1.50(2) 2_656 ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 Cl8 1.712(16) . ?
C14 Cl7 1.734(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N3 C15 1.112(12) . ?
C15 C16 1.485(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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_4
C9 N1 C1 C2 6.0(15) .
C7 N1 C1 C2 -160.2(9) .
C9 N1 C1 C6 -174.7(10) .
C7 N1 C1 C6 19.1(12) .
N1 C1 C2 C3 -177.6(9) .
C6 C1 C2 C3 3.1(14) .
C1 C2 C3 C4 3.2(15) .
C13 N2 C4 C3 180.0(10) .
C11 N2 C4 C3 14.6(13) .
C13 N2 C4 C5 -0.2(15) .
C11 N2 C4 C5 -165.6(9) .
C2 C3 C4 N2 174.2(9) .
C2 C3 C4 C5 -5.6(14) .
N2 C4 C5 C6 -178.1(9) .
C3 C4 C5 C6 1.7(14) .
C4 C5 C6 C1 4.6(16) .
N1 C1 C6 C5 173.7(9) .
C2 C1 C6 C5 -6.9(14) .
C1 N1 C7 C8 71.2(10) .
C9 N1 C7 C8 -95.9(11) .
C1 N1 C9 C10 119.4(9) .
C7 N1 C9 C10 -73.7(11) .
N1 C9 C10 C13 -62.1(11) 2_656
C4 N2 C11 C12 68.9(11) .
C13 N2 C11 C12 -98.0(12) .
C4 N2 C13 C10 119.1(10) 2_656
C11 N2 C13 C10 -74.8(12) 2_656
