#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/82/4108261.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_4108261
loop_
_publ_author_name
'Stephen F. Nelsen'
'Gaoquan Li'
'Kevin P. Schultz'
'Hieu Q. Tran'
'Ilia A. Guzei'
'Dennis H. Evans'
_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
;
 Alkylated Trimethylene-Bridged Bis(p-Phenylenediamines)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11620
_journal_page_last               11622
_journal_paper_doi               10.1021/ja802292g
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C26 H38 F12 N6 Sb2'
_chemical_formula_sum            'C26 H38 F12 N6 Sb2'
_chemical_formula_weight         906.12
_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                113.7150(10)
_cell_angle_beta                 109.4020(10)
_cell_angle_gamma                94.5840(10)
_cell_formula_units_Z            1
_cell_length_a                   7.6010(7)
_cell_length_b                   11.2909(10)
_cell_length_c                   11.3686(10)
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.03
_cell_volume                     816.40(13)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2000)'
_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 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker CCD-1000 area detector'
_diffrn_measurement_method       '0.30° ω and 0.4 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12317
_diffrn_reflns_theta_full        30.47
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.751
_exptl_absorpt_correction_T_max  0.7208
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_description       block
_exptl_crystal_F_000             446
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0324P)²+0.3770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0607
_reflns_number_gt                4175
_reflns_number_total             4589
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja802292g_si_004.cif
_cod_data_source_block           nelsen16
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4108261
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 0.78826(2) 0.755315(12) 0.254112(12) 0.02276(5) Uani 1 1 d . . .
F1 F 0.6703(3) 0.65946(13) 0.05872(14) 0.0442(4) Uani 1 1 d . . .
F2 F 0.7272(3) 0.59710(14) 0.26578(16) 0.0458(4) Uani 1 1 d . . .
F3 F 0.5532(2) 0.79024(14) 0.25931(15) 0.0370(3) Uani 1 1 d . . .
F4 F 0.9004(2) 0.84589(16) 0.44936(14) 0.0441(4) Uani 1 1 d . . .
F5 F 0.8474(2) 0.91105(12) 0.23972(14) 0.0355(3) Uani 1 1 d . . .
F6 F 1.0219(3) 0.71981(19) 0.2479(2) 0.0567(5) Uani 1 1 d . . .
N3 N 0.1867(3) 0.8241(2) 0.9454(2) 0.0407(5) Uani 1 1 d . . .
C1 C 0.2858(2) 0.34782(17) 0.31143(17) 0.0171(3) Uani 1 1 d . A .
C2 C 0.3300(3) 0.44595(18) 0.26910(18) 0.0201(3) Uani 1 1 d . . .
H2 H 0.3492 0.4189 0.1846 0.024 Uiso 1 1 calc R . .
C3 C 0.3449(3) 0.57774(17) 0.34798(18) 0.0203(3) Uani 1 1 d . . .
H3 H 0.3757 0.6405 0.3175 0.024 Uiso 1 1 calc R . .
C4 C 0.3155(2) 0.62363(17) 0.47482(18) 0.0185(3) Uani 1 1 d . . .
C5 C 0.2591(3) 0.52461(18) 0.51126(19) 0.0217(3) Uani 1 1 d . . .
H5 H 0.2292 0.5506 0.5915 0.026 Uiso 1 1 calc R . .
C6 C 0.2468(3) 0.39316(18) 0.43381(19) 0.0211(3) Uani 1 1 d . . .
H6 H 0.2111 0.3302 0.4626 0.025 Uiso 1 1 calc R . .
N1 N 0.2819(2) 0.21814(15) 0.23833(15) 0.0190(3) Uani 1 1 d . . .
C7 C 0.2936(6) 0.1766(3) 0.1021(4) 0.0223(7) Uani 0.613(5) 1 d P A 1
H7A H 0.1778 0.1839 0.0369 0.033 Uiso 0.613(5) 1 calc PR A 1
H7B H 0.3037 0.0837 0.0653 0.033 Uiso 0.613(5) 1 calc PR A 1
H7C H 0.4074 0.2342 0.1130 0.033 Uiso 0.613(5) 1 calc PR A 1
C8 C 0.2213(14) 0.1132(14) 0.2671(15) 0.0225(17) Uani 0.613(5) 1 d P A 1
H8A H 0.1126 0.0444 0.1824 0.027 Uiso 0.613(5) 1 calc PR A 1
H8B H 0.1750 0.1498 0.3431 0.027 Uiso 0.613(5) 1 calc PR A 1
C9 C 0.3842(5) 0.0484(3) 0.3104(3) 0.0236(7) Uani 0.613(5) 1 d P A 1
H9A H 0.4328 0.0156 0.2353 0.028 Uiso 0.613(5) 1 calc PR A 1
H9B H 0.3303 -0.0302 0.3173 0.028 Uiso 0.613(5) 1 calc PR A 1
C10 C 0.5548(7) 0.1393(4) 0.4493(5) 0.0251(8) Uani 0.613(5) 1 d P A 1
H10A H 0.5065 0.1780 0.5239 0.030 Uiso 0.613(5) 1 calc PR A 1
H10B H 0.6422 0.0850 0.4748 0.030 Uiso 0.613(5) 1 calc PR A 1
C11 C 0.7460(9) 0.2103(6) 0.3397(6) 0.0295(13) Uani 0.613(5) 1 d P A 1
H11A H 0.6665 0.2225 0.2596 0.044 Uiso 0.613(5) 1 calc PR A 1
H11B H 0.7529 0.1169 0.3077 0.044 Uiso 0.613(5) 1 calc PR A 1
H11C H 0.8759 0.2682 0.3824 0.044 Uiso 0.613(5) 1 calc PR A 1
C7A C 0.174(2) 0.110(2) 0.256(2) 0.022(3) Uani 0.387(5) 1 d P A 2
H7A1 H 0.2396 0.1210 0.3511 0.033 Uiso 0.387(5) 1 calc PR A 2
H7A2 H 0.1721 0.0219 0.1879 0.033 Uiso 0.387(5) 1 calc PR A 2
H7A3 H 0.0419 0.1186 0.2398 0.033 Uiso 0.387(5) 1 calc PR A 2
C8A C 0.3802(9) 0.1642(5) 0.1395(6) 0.0208(11) Uani 0.387(5) 1 d P A 2
H8A1 H 0.4422 0.2390 0.1308 0.025 Uiso 0.387(5) 1 calc PR A 2
H8A2 H 0.2815 0.1010 0.0457 0.025 Uiso 0.387(5) 1 calc PR A 2
C9A C 0.5322(7) 0.0928(4) 0.1852(5) 0.0202(11) Uani 0.387(5) 1 d P A 2
H9A1 H 0.4724 0.0226 0.2012 0.024 Uiso 0.387(5) 1 calc PR A 2
H9A2 H 0.5735 0.0479 0.1077 0.024 Uiso 0.387(5) 1 calc PR A 2
C10A C 0.7103(17) 0.1841(10) 0.3177(12) 0.0251(8) Uani 0.387(5) 1 d P A 2
H10C H 0.8058 0.1319 0.3353 0.030 Uiso 0.387(5) 1 calc PR A 2
H10D H 0.7695 0.2559 0.3036 0.030 Uiso 0.387(5) 1 calc PR A 2
C11A C 0.6219(10) 0.1410(6) 0.4912(8) 0.0241(13) Uani 0.387(5) 1 d P A 2
H11D H 0.7293 0.1605 0.5788 0.036 Uiso 0.387(5) 1 calc PR A 2
H11E H 0.6088 0.0518 0.4192 0.036 Uiso 0.387(5) 1 calc PR A 2
H11F H 0.5027 0.1440 0.5068 0.036 Uiso 0.387(5) 1 calc PR A 2
N2 N 0.6607(2) 0.24508(16) 0.44250(16) 0.0219(3) Uani 1 1 d . . .
C12 C 0.1713(3) 0.6140(2) 0.9855(3) 0.0338(5) Uani 1 1 d . . .
H12A H 0.1485 0.6339 1.0707 0.051 Uiso 1 1 calc R . .
H12B H 0.2929 0.5872 0.9957 0.051 Uiso 1 1 calc R . .
H12C H 0.0656 0.5412 0.9050 0.051 Uiso 1 1 calc R . .
C13 C 0.1819(3) 0.7323(2) 0.9637(2) 0.0259(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 0.0000 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'
Sb Sb -0.5866 1.5461 '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
F5 Sb1 F4 92.08(6) . yes
F5 Sb1 F6 89.98(7) . yes
F4 Sb1 F6 91.22(8) . yes
F5 Sb1 F1 89.92(6) . yes
F4 Sb1 F1 177.85(6) . yes
F6 Sb1 F1 89.59(8) . yes
F5 Sb1 F3 90.07(6) . yes
F4 Sb1 F3 89.09(7) . yes
F6 Sb1 F3 179.68(8) . yes
F1 Sb1 F3 90.09(7) . yes
F5 Sb1 F2 179.18(5) . yes
F4 Sb1 F2 88.75(7) . yes
F6 Sb1 F2 89.97(8) . yes
F1 Sb1 F2 89.26(7) . yes
F3 Sb1 F2 89.97(7) . yes
N1 C1 C6 121.66(16) . ?
N1 C1 C2 121.62(16) . ?
C6 C1 C2 116.72(16) . ?
C3 C2 C1 121.20(17) . ?
C3 C2 H2 119.4 . ?
C1 C2 H2 119.4 . ?
C2 C3 C4 121.74(17) . ?
C2 C3 H3 119.1 . ?
C4 C3 H3 119.1 . ?
N2 C4 C5 121.06(17) 2_666 ?
N2 C4 C3 122.22(17) 2_666 ?
C5 C4 C3 116.71(16) . ?
C6 C5 C4 121.57(17) . ?
C6 C5 H5 119.2 . ?
C4 C5 H5 119.2 . ?
C5 C6 C1 121.85(17) . ?
C5 C6 H6 119.1 . ?
C1 C6 H6 119.1 . ?
C1 N1 C8 124.4(5) . ?
C1 N1 C7 117.73(19) . ?
C8 N1 C7 116.1(6) . ?
C1 N1 C8A 126.7(2) . ?
C8 N1 C8A 107.5(5) . ?
C7 N1 C8A 27.8(2) . ?
C1 N1 C7A 119.9(8) . ?
C8 N1 C7A 12.3(10) . ?
C7 N1 C7A 116.0(9) . ?
C8A N1 C7A 113.4(8) . ?
N1 C7 H7A 109.5 . ?
N1 C7 H7B 109.5 . ?
N1 C7 H7C 109.5 . ?
N1 C8 C9 112.0(7) . ?
N1 C8 H8A 109.2 . ?
C9 C8 H8A 109.2 . ?
N1 C8 H8B 109.2 . ?
C9 C8 H8B 109.2 . ?
H8A C8 H8B 107.9 . ?
C8 C9 C10 115.4(6) . ?
C8 C9 H9A 108.4 . ?
C10 C9 H9A 108.4 . ?
C8 C9 H9B 108.4 . ?
C10 C9 H9B 108.4 . ?
H9A C9 H9B 107.5 . ?
N2 C10 C9 112.6(3) . ?
N2 C10 H10A 109.1 . ?
C9 C10 H10A 109.1 . ?
N2 C10 H10B 109.1 . ?
C9 C10 H10B 109.1 . ?
H10A C10 H10B 107.8 . ?
N2 C11 H11A 109.5 . ?
N2 C11 H11B 109.5 . ?
N2 C11 H11C 109.5 . ?
N1 C7A H7A1 109.5 . ?
N1 C7A H7A2 109.5 . ?
H7A1 C7A H7A2 109.5 . ?
N1 C7A H7A3 109.5 . ?
H7A1 C7A H7A3 109.5 . ?
H7A2 C7A H7A3 109.5 . ?
N1 C8A C9A 114.1(4) . ?
N1 C8A H8A1 108.7 . ?
C9A C8A H8A1 108.7 . ?
N1 C8A H8A2 108.7 . ?
C9A C8A H8A2 108.7 . ?
H8A1 C8A H8A2 107.6 . ?
C10A C9A C8A 114.5(6) . ?
C10A C9A H9A1 108.6 . ?
C8A C9A H9A1 108.6 . ?
C10A C9A H9A2 108.6 . ?
C8A C9A H9A2 108.6 . ?
H9A1 C9A H9A2 107.6 . ?
N2 C10A C9A 111.5(8) . ?
N2 C10A H10C 109.3 . ?
C9A C10A H10C 109.3 . ?
N2 C10A H10D 109.3 . ?
C9A C10A H10D 109.3 . ?
H10C C10A H10D 108.0 . ?
N2 C11A H11D 109.5 . ?
N2 C11A H11E 109.5 . ?
H11D C11A H11E 109.5 . ?
N2 C11A H11F 109.5 . ?
H11D C11A H11F 109.5 . ?
H11E C11A H11F 109.5 . ?
C4 N2 C10 123.8(2) 2_666 ?
C4 N2 C11 117.9(3) 2_666 ?
C10 N2 C11 118.3(3) . ?
C4 N2 C10A 127.9(4) 2_666 ?
C10 N2 C10A 107.6(5) . ?
C11 N2 C10A 12.6(5) . ?
C4 N2 C11A 120.3(3) 2_666 ?
C10 N2 C11A 21.5(2) . ?
C11 N2 C11A 117.4(4) . ?
C10A N2 C11A 110.2(5) . ?
C13 C12 H12A 109.5 . ?
C13 C12 H12B 109.5 . ?
H12A C12 H12B 109.5 . ?
C13 C12 H12C 109.5 . ?
H12A C12 H12C 109.5 . ?
H12B C12 H12C 109.5 . ?
N3 C13 C12 178.8(2) . ?
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 F5 1.8641(12) . yes
Sb1 F4 1.8647(13) . yes
Sb1 F6 1.8695(15) . yes
Sb1 F1 1.8701(13) . yes
Sb1 F3 1.8750(13) . yes
Sb1 F2 1.8770(13) . yes
N3 C13 1.137(3) . ?
C1 N1 1.354(2) . ?
C1 C6 1.418(2) . ?
C1 C2 1.431(2) . ?
C2 C3 1.365(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(3) . ?
C3 H3 0.9500 . ?
C4 N2 1.355(2) 2_666 ?
C4 C5 1.421(3) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C8 1.430(14) . ?
N1 C7 1.463(3) . ?
N1 C8A 1.508(5) . ?
N1 C7A 1.53(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.530(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.534(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.429(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.455(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A C9A 1.530(8) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.529(11) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A N2 1.496(14) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A N2 1.534(7) . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
N2 C4 1.355(2) 2_666 ?
C12 C13 1.454(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N1 C1 C2 C3 -176.06(17) . .
C6 C1 C2 C3 3.8(3) . .
C1 C2 C3 C4 -0.6(3) . .
C2 C3 C4 N2 176.66(17) . 2_666
C2 C3 C4 C5 -3.5(3) . .
N2 C4 C5 C6 -175.69(18) 2_666 .
C3 C4 C5 C6 4.4(3) . .
C4 C5 C6 C1 -1.3(3) . .
N1 C1 C6 C5 177.00(17) . .
C2 C1 C6 C5 -2.9(3) . .
C6 C1 N1 C8 6.3(6) . .
C2 C1 N1 C8 -173.8(5) . .
C6 C1 N1 C7 170.5(2) . .
C2 C1 N1 C7 -9.6(3) . .
C6 C1 N1 C8A -158.3(3) . .
C2 C1 N1 C8A 21.6(4) . .
C6 C1 N1 C7A 19.8(9) . .
C2 C1 N1 C7A -160.3(9) . .
C1 N1 C8 C9 -117.1(7) . .
C7 N1 C8 C9 78.5(9) . .
C8A N1 C8 C9 50.0(10) . .
C7A N1 C8 C9 171(7) . .
N1 C8 C9 C10 65.2(10) . .
C8 C9 C10 N2 -67.2(7) . .
C1 N1 C8A C9A 117.6(4) . .
C8 N1 C8A C9A -49.1(6) . .
C7 N1 C8A C9A -162.2(8) . .
C7A N1 C8A C9A -60.6(9) . .
N1 C8A C9A C10A -67.6(7) . .
C8A C9A C10A N2 63.9(9) . .
C9 C10 N2 C4 120.0(3) . 2_666
C9 C10 N2 C11 -59.1(5) . .
C9 C10 N2 C10A -51.8(6) . .
C9 C10 N2 C11A -152.4(13) . .
C9A C10A N2 C4 -119.4(6) . 2_666
C9A C10A N2 C10 52.0(9) . .
C9A C10A N2 C11 -159(4) . .
C9A C10A N2 C11A 74.7(9) . .
