#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/74/7117423.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_7117423
loop_
_publ_author_name
'S. Menichetti'
'S. Cecchi'
'P. Procacci'
'M. Innocenti'
'L. Becucci'
'L. Franco'
'C. Viglianisi'
_publ_section_title
;
 Thia-bridged triarylamine heterohelicene radical cations as redox-driven
 molecular switches
;
_journal_name_full               Chem.Commun.
_journal_page_first              11452
_journal_paper_doi               10.1039/C5cc04007H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C22 H19 Cl2 F6 N O3 S2 Sb'
_chemical_formula_sum            'C22 H19 Cl2 F6 N O3 S2 Sb'
_chemical_formula_weight         716.15
_chemical_name_systematic
;
2,3,4-trimethoxybenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazinyl
hexafluoroantimonate, free radical
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_date
;
'Wed May 09 15:26:04 2012'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_audit_update_record
;
2013-03-27 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                102.819(5)
_cell_angle_beta                 97.906(4)
_cell_angle_gamma                112.771(5)
_cell_formula_units_Z            2
_cell_length_a                   9.106(1)
_cell_length_b                   10.580(1)
_cell_length_c                   15.856(1)
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.7253
_cell_measurement_theta_min      4.7500
_cell_volume                     1330.3(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
1 omega -25.00 62.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 77.0000 0.0000 87

2 omega -75.00 -35.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 179.0000 90.0000 40

3 omega 34.00 70.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 37.0000 -90.0000 36

4 omega -121.00 -90.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 125.0000 -90.0000 31

5 omega -37.00 -6.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 125.0000 -90.0000 31

6 omega -33.00 -7.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 77.0000 -120.0000 26

7 omega -103.00 -55.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 77.0000 -120.0000 48

8 omega 46.00 71.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 30.0000 25

9 omega 75.00 143.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 37.0000 -150.0000 68

10 omega 15.00 70.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 90.0000 55

11 omega 15.00 96.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 -60.0000 81

12 omega 16.00 80.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 -120.0000 64

13 omega 14.00 109.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 30.0000 95

14 omega 13.00 67.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 -60.0000 54

15 omega 76.00 150.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 37.0000 90.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7657
_diffrn_reflns_theta_full        61.82
_diffrn_reflns_theta_max         61.82
_diffrn_reflns_theta_min         4.75
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    12.175
_exptl_absorpt_correction_T_max  0.6145
_exptl_absorpt_correction_T_min  0.3776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            darkviolet
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.689
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0687
_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)+(0.1219P)²+1.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2066
_reflns_number_gt                2857
_reflns_number_total             4050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04007h2.cif
_cod_data_source_block           exp_711
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117423
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
N1 N 0.5005(8) -0.2338(7) 0.0936(4) 0.0461(16) Uani 1 1 d . . .
O1 O 0.1294(8) -0.5027(7) 0.2429(5) 0.0647(17) Uani 1 1 d . . .
O2 O 0.3504(9) -0.3343(8) 0.4070(4) 0.074(2) Uani 1 1 d . . .
O3 O 0.6470(8) -0.1293(7) 0.4138(4) 0.0641(18) Uani 1 1 d . . .
F1 F 0.1674(10) 0.1165(9) 0.3724(5) 0.119(3) Uani 1 1 d . . .
F2 F 0.0474(16) -0.1607(10) 0.3054(8) 0.170(5) Uani 1 1 d . . .
F3 F 0.3597(12) -0.0051(12) 0.3229(7) 0.151(4) Uani 1 1 d . . .
F4 F -0.0285(12) -0.0133(15) 0.2154(8) 0.183(5) Uani 1 1 d . . .
F5 F 0.1646(11) -0.1305(9) 0.1662(6) 0.130(3) Uani 1 1 d . . .
F6 F 0.2890(13) 0.1492(10) 0.2370(6) 0.134(3) Uani 1 1 d . . .
S1 S 0.7172(4) -0.1952(4) -0.03643(19) 0.0771(8) Uani 1 1 d . . .
S2 S 0.1706(3) -0.4896(3) 0.07363(15) 0.0585(6) Uani 1 1 d . . .
Sb1 Sb 0.16343(8) -0.00637(7) 0.26862(4) 0.0656(3) Uani 1 1 d . . .
C1 C 0.4359(11) -0.3430(10) 0.0119(6) 0.053(2) Uani 1 1 d . . .
C2 C 0.5188(12) -0.3313(12) -0.0558(6) 0.061(3) Uani 1 1 d . . .
C3 C 0.4489(17) -0.4358(14) -0.1387(7) 0.077(3) Uani 1 1 d . . .
H3 H 0.5044 -0.4274 -0.1837 0.092 Uiso 1 1 calc R . .
C4 C 0.2986(16) -0.5516(12) -0.1553(6) 0.069(3) Uani 1 1 d . . .
H4 H 0.2524 -0.6205 -0.2111 0.083 Uiso 1 1 calc R . .
C5 C 0.2189(14) -0.5636(11) -0.0888(6) 0.069(3) Uani 1 1 d . . .
H5 H 0.1173 -0.6412 -0.0998 0.083 Uiso 1 1 calc R . .
C6 C 0.2854(11) -0.4637(10) -0.0060(6) 0.054(2) Uani 1 1 d . . .
C7 C 0.5971(10) -0.0889(10) 0.0958(6) 0.050(2) Uani 1 1 d . . .
C8 C 0.6990(11) -0.0575(11) 0.0398(6) 0.057(2) Uani 1 1 d . . .
C9 C 0.7903(12) 0.0856(14) 0.0444(8) 0.072(3) Uani 1 1 d . . .
H9 H 0.8608 0.1071 0.0071 0.087 Uiso 1 1 calc R . .
C10 C 0.7773(14) 0.1946(14) 0.1034(9) 0.083(4) Uani 1 1 d . . .
H10 H 0.8411 0.2898 0.1073 0.100 Uiso 1 1 calc R . .
C11 C 0.6720(12) 0.1637(11) 0.1555(8) 0.068(3) Uani 1 1 d . . .
H11 H 0.6620 0.2385 0.1941 0.082 Uiso 1 1 calc R . .
C12 C 0.5762(11) 0.0212(10) 0.1535(7) 0.057(2) Uani 1 1 d . . .
H12 H 0.5020 0.0008 0.1890 0.069 Uiso 1 1 calc R . .
C13 C 0.4656(10) -0.2639(8) 0.1726(5) 0.0436(19) Uani 1 1 d . . .
C14 C 0.3191(10) -0.3755(8) 0.1712(6) 0.045(2) Uani 1 1 d . . .
C15 C 0.2807(10) -0.3964(9) 0.2504(6) 0.047(2) Uani 1 1 d . . .
C16 C 0.3914(11) -0.3093(10) 0.3318(6) 0.053(2) Uani 1 1 d . . .
C17 C 0.5449(10) -0.2023(10) 0.3321(6) 0.051(2) Uani 1 1 d . . .
C18 C 0.5818(10) -0.1787(9) 0.2544(5) 0.0440(19) Uani 1 1 d . . .
H18 H 0.6825 -0.1072 0.2557 0.053 Uiso 1 1 calc R . .
C19 C 0.1208(18) -0.6075(15) 0.2841(10) 0.122(6) Uani 1 1 d . . .
H19A H 0.0080 -0.6744 0.2735 0.183 Uiso 1 1 calc R . .
H19B H 0.1673 -0.5630 0.3472 0.183 Uiso 1 1 calc R . .
H19C H 0.1812 -0.6575 0.2601 0.183 Uiso 1 1 calc R . .
C20 C 0.3520(18) -0.2226(15) 0.4750(9) 0.098(4) Uani 1 1 d . . .
H20A H 0.3208 -0.2576 0.5238 0.146 Uiso 1 1 calc R . .
H20B H 0.2758 -0.1888 0.4522 0.146 Uiso 1 1 calc R . .
H20C H 0.4606 -0.1450 0.4956 0.146 Uiso 1 1 calc R . .
C21 C 0.8091(4) -0.0129(4) 0.4184(3) 0.084(4) Uani 1 1 d . . .
H21A H 0.8720 0.0313 0.4794 0.126 Uiso 1 1 calc R . .
H21B H 0.7919 0.0579 0.3950 0.126 Uiso 1 1 calc R . .
H21C H 0.8678 -0.0531 0.3837 0.126 Uiso 1 1 calc R . .
Cl1 Cl 0.4327(4) -0.4357(4) 0.6183(3) 0.1418(16) Uani 1 1 d R . .
Cl2 Cl 0.1153(4) -0.6470(4) 0.5787(3) 0.299(5) Uani 1 1 d R . .
C22 C 0.2951(4) -0.5789(4) 0.5405(3) 0.143(6) Uani 1 1 d R . .
H22A H 0.3366 -0.6509 0.5272 0.172 Uiso 1 1 calc R . .
H22B H 0.2706 -0.5548 0.4863 0.172 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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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'
Cl Cl 0.3639 0.7018 '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
C1 N1 C13 120.8(7) . .
C1 N1 C7 119.3(7) . .
C13 N1 C7 119.8(7) . .
C15 O1 C19 118.5(9) . .
C16 O2 C20 119.9(8) . .
C17 O3 C21 116.5(6) . .
C2 S1 C8 98.7(4) . .
C14 S2 C6 101.1(4) . .
F4 Sb1 F6 94.2(6) . .
F4 Sb1 F2 89.0(6) . .
F6 Sb1 F2 176.7(5) . .
F4 Sb1 F1 90.0(5) . .
F6 Sb1 F1 89.2(4) . .
F2 Sb1 F1 89.7(4) . .
F4 Sb1 F5 91.7(5) . .
F6 Sb1 F5 91.0(4) . .
F2 Sb1 F5 90.0(4) . .
F1 Sb1 F5 178.3(4) . .
F4 Sb1 F3 178.3(5) . .
F6 Sb1 F3 87.2(5) . .
F2 Sb1 F3 89.7(6) . .
F1 Sb1 F3 91.1(4) . .
F5 Sb1 F3 87.3(4) . .
C2 C1 N1 120.1(9) . .
C2 C1 C6 118.0(9) . .
N1 C1 C6 121.9(8) . .
C3 C2 C1 119.7(10) . .
C3 C2 S1 118.7(8) . .
C1 C2 S1 121.4(8) . .
C4 C3 C2 121.2(10) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C5 C4 C3 119.0(9) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
C4 C5 C6 121.3(11) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 120.8(10) . .
C5 C6 S2 117.2(8) . .
C1 C6 S2 122.0(7) . .
C8 C7 C12 120.4(9) . .
C8 C7 N1 121.8(9) . .
C12 C7 N1 117.7(8) . .
C7 C8 C9 119.5(10) . .
C7 C8 S1 120.6(8) . .
C9 C8 S1 119.9(8) . .
C10 C9 C8 120.7(10) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C11 C10 C9 119.8(11) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C12 121.9(12) . .
C10 C11 H11 119.0 . .
C12 C11 H11 119.0 . .
C7 C12 C11 117.4(10) . .
C7 C12 H12 121.3 . .
C11 C12 H12 121.3 . .
C14 C13 N1 121.3(7) . .
C14 C13 C18 119.7(7) . .
N1 C13 C18 118.9(7) . .
C15 C14 C13 120.5(8) . .
C15 C14 S2 116.1(6) . .
C13 C14 S2 123.3(6) . .
O1 C15 C16 123.2(8) . .
O1 C15 C14 116.6(7) . .
C16 C15 C14 120.2(8) . .
O2 C16 C15 118.4(8) . .
O2 C16 C17 122.9(8) . .
C15 C16 C17 118.7(8) . .
O3 C17 C18 124.5(8) . .
O3 C17 C16 114.1(7) . .
C18 C17 C16 121.4(8) . .
C17 C18 C13 119.3(8) . .
C17 C18 H18 120.4 . .
C13 C18 H18 120.4 . .
O1 C19 H19A 109.5 . .
O1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O2 C20 H20A 109.5 . .
O2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O3 C21 H21A 109.5 . .
O3 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O3 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
Cl1 C22 Cl2 108.6 . .
Cl1 C22 H22A 110.0 . .
Cl2 C22 H22A 110.0 . .
Cl1 C22 H22B 110.0 . .
Cl2 C22 H22B 110.0 . .
H22A C22 H22B 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.400(11) .
N1 C13 1.406(10) .
N1 C7 1.432(11) .
O1 C15 1.369(10) .
O1 C19 1.389(13) .
O2 C16 1.348(10) .
O2 C20 1.406(14) .
O3 C17 1.345(10) .
O3 C21 1.492(7) .
F1 Sb1 1.843(7) .
F2 Sb1 1.839(8) .
F3 Sb1 1.867(8) .
F4 Sb1 1.800(8) .
F5 Sb1 1.853(7) .
F6 Sb1 1.826(8) .
S1 C2 1.751(11) .
S1 C8 1.752(11) .
S2 C14 1.735(8) .
S2 C6 1.748(10) .
C1 C2 1.396(13) .
C1 C6 1.402(13) .
C2 C3 1.390(15) .
C3 C4 1.380(16) .
C3 H3 0.9300 .
C4 C5 1.361(15) .
C4 H4 0.9300 .
C5 C6 1.370(12) .
C5 H5 0.9300 .
C7 C8 1.372(12) .
C7 C12 1.406(13) .
C8 C9 1.395(14) .
C9 C10 1.370(17) .
C9 H9 0.9300 .
C10 C11 1.344(16) .
C10 H10 0.9300 .
C11 C12 1.410(13) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.391(11) .
C13 C18 1.407(11) .
C14 C15 1.390(11) .
C15 C16 1.388(12) .
C16 C17 1.417(12) .
C17 C18 1.370(11) .
C18 H18 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
Cl1 C22 1.6320 .
Cl2 C22 1.7663 .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
