#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:39:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178401 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/23/4022367.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_4022367
loop_
_publ_author_name
'S. V. Rosokha'
'S. V. Lindeman'
'R. Rathore'
'J. K. Kochi'
_publ_section_title
;
 Molecular Recognition of NO/NO⁺ via Multicenter (Charge-Transfer)
 Binding to Bridged Diarene Donors. Effect of Structure on
 the Optical Transitions and Complexation Thermodynamics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3947
_journal_page_last               3957
_journal_paper_doi               10.1021/jo030015q
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'chemical synthesis'
_chemical_formula_moiety
;
(C26 H32), 4(N O)^+^, 4(Sb Cl6)^-^, 2(C H2 Cl2)
;
_chemical_formula_sum            'C28 H36 Cl28 N4 O4 Sb4'
_chemical_formula_weight         1972.21
_chemical_name_systematic
;
2,3-bis(2,4,6-trimethyl)phenylbicyclo(2.2)octa-2-ene/
nitrosonium hexafluoroantimonate molecular complex 14
dichloromethane disolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.000(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.870(2)
_cell_length_b                   20.407(3)
_cell_length_c                   28.548(5)
_cell_measurement_reflns_used    8109
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     6333.0(19)
_computing_cell_refinement       'SAINT V6.01 (BrukerAXS, 1997-99)'
_computing_data_collection       'SMART V5.054 (BrukerAXS, 1997-98)'
_computing_data_reduction        'SAINT & SADABS (Sheldrick, 1998)'
_computing_molecular_graphics    'XP V5.06 (BrukerAXS, 1997-99)'
_computing_publication_material  'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Siemens SMART 1K'
_diffrn_measurement_method
;
ω-scan, frame range 0.3 deg, hemisphere
;
_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  0.1572
_diffrn_reflns_av_sigmaI/netI    0.0761
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            33265
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             3776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.25
_refine_diff_density_max         3.067
_refine_diff_density_min         -2.798
_refine_diff_density_rms         0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.049
_refine_ls_goodness_of_fit_obs   1.157
_refine_ls_hydrogen_treatment
;
riding and rotating model with Uiso = 1.2Uiso/eq of an adjacent atom
(1.5Uiso/eq for Me-groups)
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         9665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_restrained_S_obs      1.157
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_obs          0.0716
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2094
_refine_ls_wR_factor_obs         0.1820
_reflns_number_observed          6520
_reflns_number_total             9937
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo030015q_s1.cif
_cod_data_source_block           ros-fx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022367
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'
'-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Sb1 Sb -0.51373(6) 0.52266(3) 0.38510(2) 0.02464(14) Uani 1 d .
Sb2 Sb 0.01216(7) 0.33451(2) 0.01142(2) 0.0298(2) Uani 1 d .
Cl1 Cl -0.7316(2) 0.5219(2) 0.39114(11) 0.0421(7) Uani 1 d .
Cl2 Cl -0.2932(2) 0.52335(14) 0.38343(11) 0.0368(6) Uani 1 d .
Cl3 Cl -0.5037(3) 0.41617(10) 0.41746(8) 0.0394(6) Uani 1 d .
Cl4 Cl -0.4992(3) 0.56904(10) 0.46182(7) 0.0306(5) Uani 1 d .
Cl5 Cl -0.5184(3) 0.63028(10) 0.35436(8) 0.0344(5) Uani 1 d .
Cl6 Cl -0.5254(3) 0.48038(12) 0.30907(8) 0.0405(6) Uani 1 d .
Cl7 Cl 0.2277(3) 0.34133(14) 0.0001(2) 0.0525(10) Uani 1 d .
Cl8 Cl -0.2049(3) 0.33642(14) 0.02072(11) 0.0393(6) Uani 1 d .
Cl9 Cl -0.0034(3) 0.25069(12) -0.04514(9) 0.0410(6) Uani 1 d .
Cl10 Cl -0.0125(3) 0.41534(14) -0.04864(12) 0.0537(8) Uani 1 d .
Cl11 Cl 0.0290(3) 0.42026(13) 0.06826(13) 0.0561(8) Uani 1 d .
Cl12 Cl 0.0364(3) 0.25597(13) 0.07054(10) 0.0484(8) Uani 1 d .
C1 C -0.1011(9) 0.6503(4) 0.2877(3) 0.024(2) Uani 1 d .
C2 C -0.2298(10) 0.6654(5) 0.2812(4) 0.033(2) Uani 1 d .
C3 C -0.2775(10) 0.7226(5) 0.3001(3) 0.029(2) Uani 1 d .
H3A H -0.3620(10) 0.7323(5) 0.2952(3) 0.035 Uiso 1 calc R
C4 C -0.2057(10) 0.7670(5) 0.3261(3) 0.031(2) Uani 1 d .
C5 C -0.0832(10) 0.7503(4) 0.3346(3) 0.028(2) Uani 1 d .
H5A H -0.0341(10) 0.7786(4) 0.3534(3) 0.033 Uiso 1 calc R
C6 C -0.0313(9) 0.6941(5) 0.3166(3) 0.028(2) Uani 1 d .
C7 C -0.3142(9) 0.6214(5) 0.2539(4) 0.030(2) Uani 1 d .
H7A H -0.3792(42) 0.6477(7) 0.2394(23) 0.045 Uiso 1 calc R
H7B H -0.3511(55) 0.5891(24) 0.2750(7) 0.045 Uiso 1 calc R
H7C H -0.2672(17) 0.5988(29) 0.2295(18) 0.045 Uiso 1 calc R
C8 C -0.2606(13) 0.8304(6) 0.3438(4) 0.045(3) Uani 1 d .
H8A H -0.2530(81) 0.8324(22) 0.3780(6) 0.068 Uiso 1 calc R
H8B H -0.3477(26) 0.8325(22) 0.3350(30) 0.068 Uiso 1 calc R
H8C H -0.2167(60) 0.8675(6) 0.3298(27) 0.068 Uiso 1 calc R
C9 C 0.1011(11) 0.6784(6) 0.3309(4) 0.039(3) Uani 1 d .
H9A H 0.1180(27) 0.6974(37) 0.3617(14) 0.058 Uiso 1 calc R
H9B H 0.1580(12) 0.6970(37) 0.3078(17) 0.058 Uiso 1 calc R
H9C H 0.1122(25) 0.6308(6) 0.3323(30) 0.058 Uiso 1 calc R
C10 C -0.0463(8) 0.5920(4) 0.2648(3) 0.023(2) Uani 1 d .
C11 C -0.0906(9) 0.5234(5) 0.2787(4) 0.030(2) Uani 1 d .
H11A H -0.1616(9) 0.5259(5) 0.3009(4) 0.036 Uiso 1 calc R
C12 C 0.0214(11) 0.4897(5) 0.3019(3) 0.034(2) Uani 1 d .
H12A H 0.0498(11) 0.5156(5) 0.3292(3) 0.040 Uiso 1 calc R
H12B H -0.0016(11) 0.4454(5) 0.3130(3) 0.040 Uiso 1 calc R
C13 C -0.1245(11) 0.4848(5) 0.2349(4) 0.038(2) Uani 1 d .
H13A H -0.2019(11) 0.5023(5) 0.2216(4) 0.045 Uiso 1 calc R
H13B H -0.1381(11) 0.4383(5) 0.2432(4) 0.045 Uiso 1 calc R
Cl1X Cl -0.0962(4) 0.3035(2) 0.30492(15) 0.0687(10) Uani 1 d .
Cl2X Cl -0.3468(4) 0.3433(2) 0.2848(2) 0.090(2) Uani 1 d .
N1 N -0.2797(8) 0.1783(4) 0.1232(3) 0.031(2) Uani 1 d .
O1 O -0.2344(8) 0.1885(4) 0.0892(3) 0.041(2) Uani 1 d .
C1X C -0.2305(16) 0.3411(8) 0.3265(7) 0.071(5) Uani 1 d .
H1XA H -0.2599(16) 0.3168(8) 0.3543(7) 0.086 Uiso 1 calc R
H1XB H -0.2109(16) 0.3864(8) 0.3365(7) 0.086 Uiso 1 calc R
O2 O -0.7773(11) 0.4944(5) 0.4944(5) 0.061(3) Uani 1 d .
N2 N -0.7287(16) 0.5228(7) 0.5149(5) 0.064(4) Uani 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'
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
_geom_angle_site_symmetry_3
Cl6 Sb1 Cl3 91.49(9) . .
Cl6 Sb1 Cl5 89.83(8) . .
Cl3 Sb1 Cl5 178.11(10) . .
Cl6 Sb1 Cl1 90.63(12) . .
Cl3 Sb1 Cl1 90.65(12) . .
Cl5 Sb1 Cl1 90.69(11) . .
Cl6 Sb1 Cl4 178.18(9) . .
Cl3 Sb1 Cl4 90.17(8) . .
Cl5 Sb1 Cl4 88.49(8) . .
Cl1 Sb1 Cl4 90.11(10) . .
Cl6 Sb1 Cl2 92.17(12) . .
Cl3 Sb1 Cl2 88.11(11) . .
Cl5 Sb1 Cl2 90.49(10) . .
Cl1 Sb1 Cl2 176.97(10) . .
Cl4 Sb1 Cl2 87.13(10) . .
Cl12 Sb2 Cl9 90.29(10) . .
Cl12 Sb2 Cl7 91.57(13) . .
Cl9 Sb2 Cl7 91.14(13) . .
Cl12 Sb2 Cl8 92.43(12) . .
Cl9 Sb2 Cl8 90.98(11) . .
Cl7 Sb2 Cl8 175.46(10) . .
Cl12 Sb2 Cl11 90.18(12) . .
Cl9 Sb2 Cl11 179.43(12) . .
Cl7 Sb2 Cl11 88.53(13) . .
Cl8 Sb2 Cl11 89.31(12) . .
Cl12 Sb2 Cl10 179.64(12) . .
Cl9 Sb2 Cl10 90.07(11) . .
Cl7 Sb2 Cl10 88.42(13) . .
Cl8 Sb2 Cl10 87.56(11) . .
Cl11 Sb2 Cl10 89.45(12) . .
C6 C1 C2 116.9(9) . .
C6 C1 C10 122.8(9) . .
C2 C1 C10 120.3(9) . .
C3 C2 C1 119.5(10) . .
C3 C2 C7 118.5(10) . .
C1 C2 C7 122.0(9) . .
C2 C3 C4 122.7(10) . .
C5 C4 C3 117.6(9) . .
C5 C4 C8 121.8(10) . .
C3 C4 C8 120.6(11) . .
C6 C5 C4 121.9(9) . .
C5 C6 C1 121.2(9) . .
C5 C6 C9 117.3(9) . .
C1 C6 C9 121.4(9) . .
C10 C10 C1 126.3(5) 2 .
C10 C10 C11 114.0(5) 2 .
C1 C10 C11 119.5(8) . .
C13 C11 C10 109.5(8) . .
C13 C11 C12 108.2(8) . .
C10 C11 C12 105.7(8) . .
C13 C12 C11 108.0(8) 2 .
C11 C13 C12 110.6(9) . 2
Cl2X C1X Cl1X 112.0(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl6 2.339(2) .
Sb1 Cl3 2.364(2) .
Sb1 Cl5 2.366(2) .
Sb1 Cl1 2.375(3) .
Sb1 Cl4 2.391(2) .
Sb1 Cl2 2.398(3) .
Sb2 Cl12 2.342(3) .
Sb2 Cl9 2.359(2) .
Sb2 Cl7 2.369(3) .
Sb2 Cl8 2.375(3) .
Sb2 Cl11 2.393(3) .
Sb2 Cl10 2.394(3) .
C1 C6 1.433(13) .
C1 C2 1.445(15) .
C1 C10 1.481(13) .
C2 C3 1.386(14) .
C2 C7 1.502(15) .
C3 C4 1.408(15) .
C4 C5 1.40(2) .
C4 C8 1.511(14) .
C5 C6 1.379(14) .
C6 C9 1.530(15) .
C10 C10 1.31(2) 2
C10 C11 1.534(13) .
C11 C13 1.524(15) .
C11 C12 1.548(15) .
C12 C13 1.54(2) 2
C13 C12 1.54(2) 2
Cl1X C1X 1.76(2) .
Cl2X C1X 1.74(2) .
N1 O1 1.108(12) .
O2 N2 0.98(2) .
