#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:32:06 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178874 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/03/4110395.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_4110395
loop_
_publ_author_name
'Shijun Zheng'
'Stephen Barlow'
'Chad Risko'
'Tiffany L. Kinnibrugh'
'Viktor N. Khrustalev'
'Simon C. Jones'
'Mikhail Yu. Antipin'
'Neil M. Tucker'
'Tatiana V. Timofeeva'
'Veaceslav Coropceanu'
'Jean-Luc Brédas'
'Seth R. Marder'
_publ_contact_author
;
Stephen Barlow
;
_publ_contact_author_email
;
stephen.barlow@chemistry.gatech.edu
;
_publ_section_title
;
 Isolation and Crystal Structures of Two Singlet Bis(Triarylamine)
 Dications with Nonquinoidal Geometries
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1812
_journal_page_last               1817
_journal_paper_doi               10.1021/ja0541534
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C42 H38 N2 O4 2+, 2(Cl6 Sb 1-)'
_chemical_formula_sum            'C42 H38 Cl12 N2 O4 Sb2'
_chemical_formula_weight         1303.64
_chemical_name_systematic
; 
 E-4,4'-Bis[4-bis(4-methoxyphenyl)amino]stilbene bis(hexachloroantimonate) 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.749(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0382(9)
_cell_length_b                   14.4404(11)
_cell_length_c                   15.2760(12)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.3
_cell_volume                     2499.3(3)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL, v. 5.10 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL, v. 5.10 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL, v. 5.10 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL, v. 5.10 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21899
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.765
_exptl_absorpt_correction_T_max  0.696
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       prism
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.977
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4897
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0414
_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)+(0.0430P)²+7.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                4108
_reflns_number_total             4897
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja0541534si20051017_112017_1.cif
_cod_data_source_block           COMPOUND_1_2SBCL6
_cod_database_code               4110395
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.37323(2) 0.24316(2) 0.007948(18) 0.04263(11) Uani 1 1 d . . .
Cl1 Cl 0.51573(12) 0.17661(16) -0.04671(12) 0.0982(6) Uani 1 1 d . . .
Cl2 Cl 0.23757(9) 0.24620(9) -0.14403(7) 0.0536(3) Uani 1 1 d . . .
Cl3 Cl 0.51002(11) 0.23800(13) 0.15953(8) 0.0841(5) Uani 1 1 d . . .
Cl4 Cl 0.22941(11) 0.30572(11) 0.06589(9) 0.0714(4) Uani 1 1 d . . .
Cl5 Cl 0.43615(14) 0.39292(11) -0.01286(11) 0.0897(5) Uani 1 1 d . . .
Cl6 Cl 0.30923(12) 0.09259(10) 0.02911(12) 0.0803(4) Uani 1 1 d . . .
O1 O -0.1331(3) 0.3725(3) 0.1852(3) 0.0742(11) Uani 1 1 d . . .
O2 O 0.6822(4) 0.5892(3) 0.3298(3) 0.0585(12) Uani 0.70 1 d PD A 1
O2' O 0.6587(7) 0.5056(6) 0.2772(7) 0.048(2) Uani 0.30 1 d PD A 2
N1 N 0.1987(2) 0.6331(2) 0.1723(2) 0.0382(7) Uani 1 1 d D . .
C1 C 0.0510(3) 0.9768(3) 0.0036(3) 0.0374(8) Uani 1 1 d . . .
H1A H 0.1014 1.0039 -0.0256 0.045 Uiso 1 1 calc R . .
C2 C 0.0876(3) 0.8917(2) 0.0508(3) 0.0353(8) Uani 1 1 d . . .
C3 C 0.0207(3) 0.8427(3) 0.0963(3) 0.0408(9) Uani 1 1 d . . .
H3A H -0.0505 0.8689 0.0991 0.049 Uiso 1 1 calc R . .
C4 C 0.0568(4) 0.7588(3) 0.1361(3) 0.0429(9) Uani 1 1 d . . .
H4A H 0.0095 0.7264 0.1648 0.052 Uiso 1 1 calc R A .
C5 C 0.1642(3) 0.7192(3) 0.1354(3) 0.0364(8) Uani 1 1 d . . .
C6 C 0.2338(3) 0.7692(3) 0.0938(3) 0.0384(8) Uani 1 1 d . . .
H6A H 0.3076 0.7449 0.0949 0.046 Uiso 1 1 calc R A .
C7 C 0.1962(3) 0.8520(3) 0.0522(3) 0.0375(8) Uani 1 1 d . . .
H7A H 0.2435 0.8841 0.0235 0.045 Uiso 1 1 calc R . .
C8 C 0.1133(3) 0.5652(3) 0.1722(3) 0.0399(8) Uani 1 1 d . . .
C9 C 0.0066(4) 0.5606(3) 0.1001(3) 0.0448(9) Uani 1 1 d . . .
H9A H -0.0081 0.6013 0.0486 0.054 Uiso 1 1 calc R A .
C10 C -0.0785(4) 0.4978(3) 0.1022(3) 0.0505(10) Uani 1 1 d . . .
H10A H -0.1525 0.4965 0.0532 0.061 Uiso 1 1 calc R . .
C11 C -0.0558(4) 0.4367(3) 0.1758(4) 0.0550(11) Uani 1 1 d . . .
C12 C 0.0525(4) 0.4390(4) 0.2466(4) 0.0652(14) Uani 1 1 d . . .
H12A H 0.0687 0.3956 0.2961 0.078 Uiso 1 1 calc R . .
C13 C 0.1366(4) 0.5027(3) 0.2465(3) 0.0536(11) Uani 1 1 d . . .
H13A H 0.2099 0.5046 0.2961 0.064 Uiso 1 1 calc R A .
C14 C -0.2460(5) 0.3668(4) 0.1151(4) 0.0798(17) Uani 1 1 d . . .
H14A H -0.2921 0.3177 0.1309 0.120 Uiso 1 1 calc R A .
H14B H -0.2366 0.3528 0.0552 0.120 Uiso 1 1 calc R . .
H14C H -0.2871 0.4261 0.1108 0.120 Uiso 1 1 calc R . .
C15 C 0.3222(5) 0.6163(9) 0.2116(13) 0.041(3) Uani 0.70 1 d PD A 1
C16 C 0.3746(6) 0.5385(6) 0.1898(9) 0.042(2) Uani 0.70 1 d PD A 1
H16A H 0.3272 0.4932 0.1489 0.051 Uiso 0.70 1 calc PR A 1
C17 C 0.4958(6) 0.5263(6) 0.2270(5) 0.0411(18) Uani 0.70 1 d PD A 1
H17A H 0.5321 0.4738 0.2104 0.049 Uiso 0.70 1 calc PR A 1
C18 C 0.5635(4) 0.5918(6) 0.2888(5) 0.0451(17) Uani 0.70 1 d PD A 1
C19 C 0.5109(5) 0.6683(5) 0.3135(5) 0.0529(17) Uani 0.70 1 d PD A 1
H19A H 0.5578 0.7129 0.3557 0.064 Uiso 0.70 1 calc PR A 1
C20 C 0.3902(5) 0.6792(5) 0.2764(5) 0.0430(17) Uani 0.70 1 d PD A 1
H20A H 0.3534 0.7300 0.2952 0.052 Uiso 0.70 1 calc PR A 1
C21 C 0.7467(9) 0.5238(6) 0.2949(8) 0.059(2) Uani 0.70 1 d PD A 1
H21A H 0.8311 0.5290 0.3304 0.089 Uiso 0.70 1 calc PR A 1
H21B H 0.7333 0.5366 0.2291 0.089 Uiso 0.70 1 calc PR A 1
H21C H 0.7197 0.4609 0.3013 0.089 Uiso 0.70 1 calc PR A 1
C15' C 0.3180(8) 0.6021(16) 0.205(3) 0.030(6) Uani 0.30 1 d PD A 2
C16' C 0.3433(11) 0.5140(10) 0.1798(17) 0.027(4) Uani 0.30 1 d PD A 2
H16B H 0.2805 0.4749 0.1447 0.032 Uiso 0.30 1 calc PR A 2
C17' C 0.4588(10) 0.4821(10) 0.2054(11) 0.039(3) Uani 0.30 1 d PD A 2
H17B H 0.4757 0.4211 0.1903 0.047 Uiso 0.30 1 calc PR A 2
C18' C 0.5491(9) 0.5421(9) 0.2538(12) 0.034(4) Uani 0.30 1 d PD A 2
C19' C 0.5270(10) 0.6325(9) 0.2743(10) 0.032(3) Uani 0.30 1 d PD A 2
H19B H 0.5900 0.6731 0.3055 0.038 Uiso 0.30 1 calc PR A 2
C20' C 0.4105(10) 0.6623(11) 0.2480(11) 0.039(4) Uani 0.30 1 d PD A 2
H20B H 0.3939 0.7244 0.2598 0.047 Uiso 0.30 1 calc PR A 2
C21' C 0.7593(14) 0.5649(14) 0.3160(17) 0.052(5) Uani 0.30 1 d PD A 2
H21D H 0.8318 0.5285 0.3294 0.078 Uiso 0.30 1 calc PR A 2
H21E H 0.7563 0.5928 0.3737 0.078 Uiso 0.30 1 calc PR A 2
H21F H 0.7583 0.6140 0.2714 0.078 Uiso 0.30 1 calc PR A 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
Cl2 Sb1 Cl3 179.15(6) .
Cl2 Sb1 Cl5 89.85(5) .
Cl3 Sb1 Cl5 90.68(5) .
Cl2 Sb1 Cl1 90.21(5) .
Cl3 Sb1 Cl1 89.11(6) .
Cl5 Sb1 Cl1 91.20(7) .
Cl2 Sb1 Cl6 90.14(5) .
Cl3 Sb1 Cl6 89.33(5) .
Cl5 Sb1 Cl6 179.76(7) .
Cl1 Sb1 Cl6 89.04(7) .
Cl2 Sb1 Cl4 90.59(4) .
Cl3 Sb1 Cl4 90.07(5) .
Cl5 Sb1 Cl4 90.53(6) .
Cl1 Sb1 Cl4 178.10(6) .
Cl6 Sb1 Cl4 89.23(6) .
C11 O1 C14 118.3(4) .
C18 O2 C21 117.7(7) .
C18' O2' C21' 119.1(13) .
C5 N1 C8 120.5(3) .
C5 N1 C15 117.2(8) .
C8 N1 C15 122.3(8) .
C5 N1 C15' 123.9(16) .
C8 N1 C15' 115.3(14) .
C1 C1 C2 125.5(5) 3_575
C1 C2 C3 123.4(3) .
C1 C2 C7 119.0(3) .
C3 C2 C7 117.5(3) .
C4 C3 C2 121.0(3) .
C3 C4 C5 120.7(4) .
N1 C5 C6 120.5(3) .
N1 C5 C4 120.9(3) .
C6 C5 C4 118.6(3) .
C7 C6 C5 120.5(3) .
C6 C7 C2 121.5(3) .
C9 C8 C13 119.5(4) .
C9 C8 N1 120.6(3) .
C13 C8 N1 119.8(4) .
C10 C9 C8 120.7(4) .
C9 C10 C11 119.7(4) .
O1 C11 C10 124.8(4) .
O1 C11 C12 115.6(4) .
C10 C11 C12 119.7(4) .
C13 C12 C11 121.1(4) .
C12 C13 C8 119.2(4) .
C16 C15 C20 119.8(6) .
C16 C15 N1 122.2(6) .
C20 C15 N1 118.0(6) .
C15 C16 C17 120.5(7) .
C16 C17 C18 119.1(6) .
O2 C18 C19 113.8(6) .
O2 C18 C17 125.5(6) .
C19 C18 C17 120.7(5) .
C20 C19 C18 119.5(6) .
C19 C20 C15 120.3(6) .
C16' C15' C20' 119.2(11) .
C16' C15' N1 118.8(10) .
C20' C15' N1 121.3(11) .
C15' C16' C17' 121.1(12) .
C16' C17' C18' 118.1(12) .
O2' C18' C19' 123.5(11) .
O2' C18' C17' 114.5(10) .
C19' C18' C17' 122.0(9) .
C18' C19' C20' 118.5(11) .
C19' C20' C15' 120.7(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl2 2.3444(10) .
Sb1 Cl3 2.3457(11) .
Sb1 Cl5 2.3482(13) .
Sb1 Cl1 2.3518(15) .
Sb1 Cl6 2.3651(13) .
Sb1 Cl4 2.3733(13) .
O1 C11 1.356(5) .
O1 C14 1.420(6) .
O2 C18 1.353(4) .
O2 C21 1.436(4) .
O2' C18' 1.351(5) .
O2' C21' 1.438(5) .
N1 C5 1.369(5) .
N1 C8 1.422(5) .
N1 C15 1.425(4) .
N1 C15' 1.425(5) .
C1 C1 1.370(7) 3_575
C1 C2 1.417(5) .
C2 C3 1.419(5) .
C2 C7 1.420(5) .
C3 C4 1.359(5) .
C4 C5 1.418(5) .
C5 C6 1.410(5) .
C6 C7 1.358(5) .
C8 C9 1.382(6) .
C8 C13 1.401(6) .
C9 C10 1.376(6) .
C10 C11 1.382(6) .
C11 C12 1.386(7) .
C12 C13 1.368(6) .
C15 C16 1.383(6) .
C15 C20 1.388(6) .
C16 C17 1.386(6) .
C17 C18 1.389(6) .
C18 C19 1.388(6) .
C19 C20 1.379(6) .
C15' C16' 1.390(7) .
C15' C20' 1.391(7) .
C16' C17' 1.390(7) .
C17' C18' 1.392(7) .
C18' C19' 1.388(7) .
C19' C20' 1.390(7) .
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
C1 C1 C2 C3 0.9(7) 3_575
C1 C1 C2 C7 -179.9(5) 3_575
C1 C2 C3 C4 176.3(4) .
C7 C2 C3 C4 -2.9(6) .
C2 C3 C4 C5 1.7(7) .
C8 N1 C5 C6 -149.0(4) .
C15 N1 C5 C6 32.2(9) .
C15' N1 C5 C6 25(2) .
C8 N1 C5 C4 29.5(6) .
C15 N1 C5 C4 -149.3(8) .
C15' N1 C5 C4 -157(2) .
C3 C4 C5 N1 -177.5(4) .
C3 C4 C5 C6 1.0(6) .
N1 C5 C6 C7 176.0(4) .
C4 C5 C6 C7 -2.6(6) .
C5 C6 C7 C2 1.3(6) .
C1 C2 C7 C6 -177.9(4) .
C3 C2 C7 C6 1.4(6) .
C5 N1 C8 C9 34.0(6) .
C15 N1 C8 C9 -147.4(9) .
C15' N1 C8 C9 -140(2) .
C5 N1 C8 C13 -145.3(4) .
C15 N1 C8 C13 33.4(10) .
C15' N1 C8 C13 40(2) .
C13 C8 C9 C10 2.5(7) .
N1 C8 C9 C10 -176.8(4) .
C8 C9 C10 C11 -2.0(7) .
C14 O1 C11 C10 -0.1(8) .
C14 O1 C11 C12 179.8(5) .
C9 C10 C11 O1 179.6(5) .
C9 C10 C11 C12 -0.3(8) .
O1 C11 C12 C13 -177.9(5) .
C10 C11 C12 C13 2.0(8) .
C11 C12 C13 C8 -1.5(8) .
C9 C8 C13 C12 -0.8(7) .
N1 C8 C13 C12 178.5(4) .
C5 N1 C15 C16 -131.0(16) .
C8 N1 C15 C16 50(2) .
C5 N1 C15 C20 51(2) .
C8 N1 C15 C20 -127.4(13) .
C20 C15 C16 C17 -5(3) .
N1 C15 C16 C17 177.7(14) .
C15 C16 C17 C18 2.0(18) .
C21 O2 C18 C19 -167.7(7) .
C21 O2 C18 C17 12.0(11) .
C16 C17 C18 O2 -179.4(8) .
C16 C17 C18 C19 0.2(12) .
O2 C18 C19 C20 179.9(7) .
C17 C18 C19 C20 0.2(11) .
C18 C19 C20 C15 -2.8(15) .
C16 C15 C20 C19 5(2) .
N1 C15 C20 C19 -177.2(12) .
C5 N1 C15' C16' -135(3) .
C8 N1 C15' C16' 39(5) .
C5 N1 C15' C20' 35(5) .
C8 N1 C15' C20' -150(3) .
C20' C15' C16' C17' 6(6) .
N1 C15' C16' C17' 177(3) .
C15' C16' C17' C18' -2(4) .
C21' O2' C18' C19' -7(3) .
C21' O2' C18' C17' 171.6(17) .
C16' C17' C18' O2' 179.2(16) .
C16' C17' C18' C19' -2(3) .
O2' C18' C19' C20' -179.1(15) .
C17' C18' C19' C20' 2(3) .
C18' C19' C20' C15' 2(3) .
C16' C15' C20' C19' -6(5) .
N1 C15' C20' C19' -176(3) .
