# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_711
_database_code_depnum_ccdc_archive 'CCDC 931338'
_audit_update_record             
;
2013-03-27 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_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)
;
_chemical_name_systematic        
;
2,3,4-trimethoxybenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazinyl
hexafluoroantimonate, free radical
;
_chemical_name_common            ?
_chemical_melting_point          ?
_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

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.106(1)
_cell_length_b                   10.580(1)
_cell_length_c                   15.856(1)
_cell_angle_alpha                102.819(5)
_cell_angle_beta                 97.906(4)
_cell_angle_gamma                112.771(5)
_cell_volume                     1330.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3037
_cell_measurement_theta_min      4.7500
_cell_measurement_theta_max      61.7253

_exptl_crystal_description       prismatic
_exptl_crystal_colour            darkviolet
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             706
_exptl_absorpt_coefficient_mu    12.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3776
_exptl_absorpt_correction_T_max  0.6145
_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_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        50
_diffrn_reflns_number            7657
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.75
_diffrn_reflns_theta_max         61.82
_reflns_number_total             4050
_reflns_number_gt                2857
_reflns_threshold_expression     >2sigma(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -25.00 62.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 77.0000 0.0000 87

#__ type_ start__ end____ width___ exp.time_
2 omega -75.00 -35.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 179.0000 90.0000 40

#__ type_ start__ end____ width___ exp.time_
3 omega 34.00 70.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 0.4688 37.0000 -90.0000 36

#__ type_ start__ end____ width___ exp.time_
4 omega -121.00 -90.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 125.0000 -90.0000 31

#__ type_ start__ end____ width___ exp.time_
5 omega -37.00 -6.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 125.0000 -90.0000 31

#__ type_ start__ end____ width___ exp.time_
6 omega -33.00 -7.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
7 omega -103.00 -55.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -77.8666 77.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
8 omega 46.00 71.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 30.0000 25

#__ type_ start__ end____ width___ exp.time_
9 omega 75.00 143.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 37.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
10 omega 15.00 70.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 90.0000 55

#__ type_ start__ end____ width___ exp.time_
11 omega 15.00 96.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 -60.0000 81

#__ type_ start__ end____ width___ exp.time_
12 omega 16.00 80.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
13 omega 14.00 109.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -77.0000 30.0000 95

#__ type_ start__ end____ width___ exp.time_
14 omega 13.00 67.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 -37.0000 -60.0000 54

#__ type_ start__ end____ width___ exp.time_
15 omega 76.00 150.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 78.8041 37.0000 90.0000 74
;

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1219P)²+1.2492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4050
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
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 . ?

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
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 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        61.82
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.689
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.127
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_732
_database_code_depnum_ccdc_archive 'CCDC 931339'
_audit_update_record             
;
2013-03-27 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_audit_creation_date             
;
'Thu May 24 12:04:54 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)
;
_chemical_name_systematic        
;
2,3,4-trimethoxybenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N O3 S2'
_chemical_formula_sum            'C21 H17 N O3 S2'
_chemical_formula_weight         395.48

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.641(1)
_cell_length_b                   14.807(1)
_cell_length_c                   23.076(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3635.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.0
_cell_measurement_reflns_used    3350
_cell_measurement_theta_min      4.1513
_cell_measurement_theta_max      70.8280

_exptl_crystal_description       prismatic
_exptl_crystal_colour            lightyellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7742
_exptl_absorpt_correction_T_max  0.9052
_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_special_details           
;
?
;
_diffrn_ambient_temperature      150.0
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        50
_diffrn_reflns_number            10195
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.47
_diffrn_reflns_theta_max         70.96
_reflns_number_total             3344
_reflns_number_gt                2293
_reflns_threshold_expression     >2sigma(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -114.00 -73.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -46.5324 -125.0000 -90.0000 41

#__ type_ start__ end____ width___ exp.time_
2 omega -11.00 68.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 46.5324 -77.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
3 omega -140.00 -70.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 -55.0000 120.0000 70

#__ type_ start__ end____ width___ exp.time_
4 omega 29.00 67.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 97.3169 -45.0000 -60.0000 38

#__ type_ start__ end____ width___ exp.time_
5 omega 30.00 56.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 97.3169 -45.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
6 omega 81.00 157.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 97.3169 125.0000 -60.0000 76

#__ type_ start__ end____ width___ exp.time_
7 omega 47.00 75.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 97.3169 -45.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
8 omega -118.00 -48.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -46.5324 -77.0000 -60.0000 70

;
_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0443P)²+1.0404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.7710(2) 0.28237(16) 0.83525(10) 0.0204(6) Uani 1 1 d . . .
O1 O 1.04469(19) 0.03758(13) 0.89607(9) 0.0269(5) Uani 1 1 d . . .
O2 O 1.18524(19) 0.15366(14) 0.95877(8) 0.0289(5) Uani 1 1 d . . .
O3 O 1.12334(19) 0.33761(14) 0.96049(8) 0.0258(5) Uani 1 1 d . . .
S1 S 0.61351(7) 0.28930(5) 0.72932(3) 0.0228(2) Uani 1 1 d . . .
S2 S 0.93552(7) 0.42841(5) 0.89220(3) 0.0229(2) Uani 1 1 d . . .
C1 C 0.7806(3) 0.36524(19) 0.80443(12) 0.0185(6) Uani 1 1 d . . .
C2 C 0.7106(3) 0.3778(2) 0.75400(12) 0.0207(7) Uani 1 1 d . . .
C3 C 0.7167(3) 0.4592(2) 0.72410(13) 0.0245(7) Uani 1 1 d . . .
H3 H 0.6671 0.4683 0.6914 0.029 Uiso 1 1 calc R . .
C4 C 0.7965(3) 0.5265(2) 0.74307(13) 0.0253(7) Uani 1 1 d . . .
H4 H 0.8032 0.5800 0.7222 0.030 Uiso 1 1 calc R . .
C5 C 0.8668(3) 0.5147(2) 0.79315(12) 0.0238(7) Uani 1 1 d . . .
H5 H 0.9208 0.5601 0.8056 0.029 Uiso 1 1 calc R . .
C6 C 0.8568(3) 0.43533(19) 0.82470(12) 0.0200(7) Uani 1 1 d . . .
C7 C 0.6500(3) 0.24384(19) 0.84327(12) 0.0191(6) Uani 1 1 d . . .
C8 C 0.5646(3) 0.24771(19) 0.79761(12) 0.0193(6) Uani 1 1 d . . .
C9 C 0.4426(3) 0.21525(19) 0.80501(13) 0.0231(7) Uani 1 1 d . . .
H9 H 0.3847 0.2199 0.7750 0.028 Uiso 1 1 calc R . .
C10 C 0.4077(3) 0.1762(2) 0.85698(13) 0.0274(7) Uani 1 1 d . . .
H10 H 0.3268 0.1536 0.8617 0.033 Uiso 1 1 calc R . .
C11 C 0.4936(3) 0.1706(2) 0.90219(13) 0.0254(7) Uani 1 1 d . . .
H11 H 0.4704 0.1438 0.9370 0.031 Uiso 1 1 calc R . .
C12 C 0.6135(3) 0.20497(19) 0.89544(12) 0.0214(7) Uani 1 1 d . . .
H12 H 0.6702 0.2020 0.9260 0.026 Uiso 1 1 calc R . .
C13 C 0.8758(3) 0.2505(2) 0.86757(12) 0.0199(6) Uani 1 1 d . . .
C14 C 0.9536(3) 0.3101(2) 0.89657(12) 0.0189(6) Uani 1 1 d . . .
C15 C 1.0565(3) 0.2762(2) 0.92809(12) 0.0205(7) Uani 1 1 d . . .
C16 C 1.0824(3) 0.1848(2) 0.92845(12) 0.0224(7) Uani 1 1 d . . .
C17 C 1.0075(3) 0.1258(2) 0.89558(12) 0.0214(7) Uani 1 1 d . . .
C18 C 0.9036(3) 0.1586(2) 0.86632(12) 0.0215(7) Uani 1 1 d . . .
H18 H 0.8522 0.1192 0.8458 0.026 Uiso 1 1 calc R . .
C19 C 1.2507(3) 0.3523(3) 0.94230(15) 0.0415(9) Uani 1 1 d . . .
H19A H 1.2897 0.3958 0.9674 0.062 Uiso 1 1 calc R . .
H19B H 1.2513 0.3746 0.9032 0.062 Uiso 1 1 calc R . .
H19C H 1.2963 0.2965 0.9441 0.062 Uiso 1 1 calc R . .
C20 C 1.1530(3) 0.1019(2) 1.00886(13) 0.0347(8) Uani 1 1 d . . .
H20A H 1.2284 0.0824 1.0280 0.052 Uiso 1 1 calc R . .
H20B H 1.1048 0.0501 0.9974 0.052 Uiso 1 1 calc R . .
H20C H 1.1042 0.1384 1.0348 0.052 Uiso 1 1 calc R . .
C21 C 0.9730(3) -0.0242(2) 0.86187(13) 0.0295(8) Uani 1 1 d . . .
H21A H 1.0077 -0.0838 0.8656 0.044 Uiso 1 1 calc R . .
H21B H 0.9757 -0.0059 0.8220 0.044 Uiso 1 1 calc R . .
H21C H 0.8874 -0.0244 0.8750 0.044 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C7 1.420(4) . ?
N1 C13 1.423(3) . ?
N1 C1 1.422(4) . ?
O1 C17 1.365(3) . ?
O1 C21 1.429(3) . ?
O2 C16 1.379(3) . ?
O2 C20 1.428(4) . ?
O3 C15 1.375(3) . ?
O3 C19 1.435(4) . ?
S1 C2 1.763(3) . ?
S1 C8 1.770(3) . ?
S2 C14 1.765(3) . ?
S2 C6 1.772(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9300 . ?
C7 C12 1.390(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.383(4) . ?
C13 C18 1.392(4) . ?
C14 C15 1.407(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.405(4) . ?
C17 C18 1.383(4) . ?
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 . ?

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
C7 N1 C13 120.6(2) . . ?
C7 N1 C1 118.5(2) . . ?
C13 N1 C1 119.5(2) . . ?
C17 O1 C21 117.0(2) . . ?
C16 O2 C20 113.6(2) . . ?
C15 O3 C19 115.5(2) . . ?
C2 S1 C8 98.24(14) . . ?
C14 S2 C6 99.14(13) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 N1 119.6(3) . . ?
C6 C1 N1 121.0(2) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 S1 120.7(2) . . ?
C1 C2 S1 118.9(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 S2 118.3(2) . . ?
C1 C6 S2 121.7(2) . . ?
C12 C7 C8 119.4(3) . . ?
C12 C7 N1 122.1(2) . . ?
C8 C7 N1 118.4(3) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 S1 119.7(2) . . ?
C9 C8 S1 120.2(2) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C14 C13 C18 120.5(3) . . ?
C14 C13 N1 120.7(3) . . ?
C18 C13 N1 118.7(3) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 S2 122.8(2) . . ?
C15 C14 S2 117.9(2) . . ?
O3 C15 C16 122.8(3) . . ?
O3 C15 C14 116.6(3) . . ?
C16 C15 C14 120.5(3) . . ?
O2 C16 C15 119.3(3) . . ?
O2 C16 C17 121.1(3) . . ?
C15 C16 C17 119.5(3) . . ?
O1 C17 C18 124.8(3) . . ?
O1 C17 C16 115.2(2) . . ?
C18 C17 C16 119.9(3) . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 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 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        70.96
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.071
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_77
_database_code_depnum_ccdc_archive 'CCDC 931340'
_audit_update_record             
;
2013-03-27 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_audit_creation_date             
;
'Thu Apr 30 13:50:52 2009'
;
_audit_creation_method           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_chemical_name_systematic        
;
3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazinyl
hexafluoroantimonate, free radical
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 F6 N S2 Sb'
_chemical_formula_sum            'C21 H17 F6 N S2 Sb'
_chemical_formula_weight         583.23

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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'

_cell_length_a                   8.543(1)
_cell_length_b                   15.622(1)
_cell_length_c                   16.383(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.989(4)
_cell_angle_gamma                90.00
_cell_volume                     2178.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8286
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      71.50

_exptl_crystal_description       prismatic
_exptl_crystal_colour            darkviolet
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1148
_exptl_absorpt_coefficient_mu    12.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2557
_exptl_absorpt_correction_T_max  0.4753
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        50
_diffrn_reflns_number            8286
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         71.50
_reflns_number_total             3934
_reflns_number_gt                2197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab


_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1187P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00037(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3934
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.2288(7) 0.4802(4) 0.7636(4) 0.0435(16) Uani 1 1 d . . .
F1 F 0.2621(13) 0.1832(6) 0.5481(5) 0.180(5) Uani 1 1 d . . .
F2 F 0.3920(12) 0.1805(6) 0.6961(7) 0.184(5) Uani 1 1 d . . .
F3 F 0.5537(15) 0.2270(7) 0.5750(13) 0.294(11) Uani 1 1 d . . .
F4 F 0.4784(9) 0.3430(4) 0.6821(5) 0.115(3) Uani 1 1 d . . .
F5 F 0.3482(15) 0.3448(6) 0.5355(5) 0.194(6) Uani 1 1 d . . .
F6 F 0.1896(10) 0.2967(7) 0.6559(6) 0.156(4) Uani 1 1 d . . .
S1 S 0.3445(3) 0.33137(14) 0.87712(15) 0.0602(6) Uani 1 1 d . . .
S2 S -0.1098(3) 0.52498(14) 0.70379(15) 0.0592(6) Uani 1 1 d . . .
Sb1 Sb 0.37194(8) 0.26050(4) 0.61510(4) 0.0685(3) Uani 1 1 d . . .
C1 C -0.1164(11) 0.3020(6) 0.8228(5) 0.057(2) Uani 1 1 d . . .
C2 C 0.0410(11) 0.2931(5) 0.8556(5) 0.052(2) Uani 1 1 d . . .
H2 H 0.0700 0.2468 0.8893 0.062 Uiso 1 1 calc R . .
C3 C 0.1517(9) 0.3526(5) 0.8379(5) 0.0466(19) Uani 1 1 d . . .
C4 C 0.1142(9) 0.4228(5) 0.7880(4) 0.0405(17) Uani 1 1 d . . .
C5 C -0.0430(10) 0.4325(5) 0.7577(5) 0.049(2) Uani 1 1 d . . .
C6 C -0.1541(10) 0.3714(6) 0.7745(5) 0.054(2) Uani 1 1 d . . .
H6 H -0.2571 0.3780 0.7521 0.064 Uiso 1 1 calc R . .
C7 C 0.0581(10) 0.5457(5) 0.6529(5) 0.050(2) Uani 1 1 d . . .
C8 C 0.2064(10) 0.5217(5) 0.6871(5) 0.048(2) Uani 1 1 d . . .
C9 C 0.3348(11) 0.5339(5) 0.6419(5) 0.056(2) Uani 1 1 d . . .
H9 H 0.4332 0.5135 0.6617 0.067 Uiso 1 1 calc R . .
C10 C 0.3168(11) 0.5768(5) 0.5664(5) 0.060(2) Uani 1 1 d . . .
H10 H 0.4037 0.5856 0.5370 0.072 Uiso 1 1 calc R . .
C11 C 0.1674(12) 0.6067(5) 0.5348(5) 0.061(2) Uani 1 1 d . . .
C12 C 0.0418(10) 0.5883(5) 0.5784(5) 0.054(2) Uani 1 1 d . . .
H12 H -0.0581 0.6050 0.5572 0.065 Uiso 1 1 calc R . .
C13 C 0.3699(9) 0.4940(5) 0.8138(5) 0.0445(19) Uani 1 1 d . . .
C14 C 0.4332(9) 0.4301(5) 0.8671(5) 0.048(2) Uani 1 1 d . . .
C15 C 0.5768(10) 0.4443(6) 0.9131(5) 0.057(2) Uani 1 1 d . . .
H15 H 0.6184 0.4021 0.9488 0.069 Uiso 1 1 calc R . .
C16 C 0.6574(10) 0.5203(7) 0.9060(5) 0.059(2) Uani 1 1 d . . .
C17 C 0.5902(10) 0.5844(6) 0.8562(5) 0.064(2) Uani 1 1 d . . .
H17 H 0.6424 0.6364 0.8528 0.076 Uiso 1 1 calc R . .
C18 C 0.4465(9) 0.5728(5) 0.8112(5) 0.053(2) Uani 1 1 d . . .
H18 H 0.4016 0.6172 0.7794 0.064 Uiso 1 1 calc R . .
C19 C -0.2370(12) 0.2361(6) 0.8393(7) 0.077(3) Uani 1 1 d . . .
H19A H -0.3369 0.2524 0.8125 0.116 Uiso 1 1 calc R . .
H19B H -0.2450 0.2320 0.8973 0.116 Uiso 1 1 calc R . .
H19C H -0.2063 0.1816 0.8188 0.116 Uiso 1 1 calc R . .
C20 C 0.1497(13) 0.6532(7) 0.4546(6) 0.080(3) Uani 1 1 d . . .
H20A H 0.2508 0.6595 0.4340 0.120 Uiso 1 1 calc R . .
H20B H 0.1051 0.7087 0.4623 0.120 Uiso 1 1 calc R . .
H20C H 0.0817 0.6212 0.4161 0.120 Uiso 1 1 calc R . .
C21 C 0.8158(11) 0.5315(7) 0.9551(6) 0.082(3) Uani 1 1 d . . .
H21A H 0.8572 0.5871 0.9446 0.123 Uiso 1 1 calc R . .
H21B H 0.8873 0.4884 0.9393 0.123 Uiso 1 1 calc R . .
H21C H 0.8027 0.5260 1.0125 0.123 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C4 1.410(9) . ?
N1 C8 1.410(9) . ?
N1 C13 1.416(9) . ?
F1 Sb1 1.834(7) . ?
F2 Sb1 1.821(8) . ?
F3 Sb1 1.815(10) . ?
F4 Sb1 1.877(6) . ?
F5 Sb1 1.852(8) . ?
F6 Sb1 1.837(8) . ?
S1 C14 1.733(8) . ?
S1 C3 1.747(8) . ?
S2 C7 1.750(9) . ?
S2 C5 1.763(8) . ?
C1 C6 1.365(12) . ?
C1 C2 1.411(12) . ?
C1 C19 1.497(12) . ?
C2 C3 1.375(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(11) . ?
C4 C5 1.399(10) . ?
C5 C6 1.390(11) . ?
C6 H6 0.9300 . ?
C7 C12 1.387(11) . ?
C7 C8 1.391(11) . ?
C8 C9 1.389(12) . ?
C9 C10 1.403(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(12) . ?
C11 C20 1.497(12) . ?
C12 H12 0.9300 . ?
C13 C18 1.396(11) . ?
C13 C14 1.403(11) . ?
C14 C15 1.400(11) . ?
C15 C16 1.383(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(13) . ?
C16 C21 1.523(12) . ?
C17 C18 1.387(11) . ?
C17 H17 0.9300 . ?
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 . ?

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
C4 N1 C8 120.1(6) . . ?
C4 N1 C13 120.6(6) . . ?
C8 N1 C13 119.3(7) . . ?
C14 S1 C3 101.7(4) . . ?
C7 S2 C5 98.5(4) . . ?
F3 Sb1 F2 92.1(7) . . ?
F3 Sb1 F1 90.2(6) . . ?
F2 Sb1 F1 89.7(5) . . ?
F3 Sb1 F6 178.8(4) . . ?
F2 Sb1 F6 88.6(6) . . ?
F1 Sb1 F6 90.8(5) . . ?
F3 Sb1 F5 89.7(7) . . ?
F2 Sb1 F5 177.8(5) . . ?
F1 Sb1 F5 91.6(4) . . ?
F6 Sb1 F5 89.6(6) . . ?
F3 Sb1 F4 91.3(6) . . ?
F2 Sb1 F4 92.0(4) . . ?
F1 Sb1 F4 177.7(4) . . ?
F6 Sb1 F4 87.7(4) . . ?
F5 Sb1 F4 86.6(4) . . ?
C6 C1 C2 117.9(8) . . ?
C6 C1 C19 121.3(9) . . ?
C2 C1 C19 120.8(8) . . ?
C3 C2 C1 120.2(8) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 122.1(7) . . ?
C2 C3 S1 115.9(6) . . ?
C4 C3 S1 121.9(6) . . ?
C3 C4 C5 117.3(7) . . ?
C3 C4 N1 122.6(7) . . ?
C5 C4 N1 120.0(7) . . ?
C6 C5 C4 120.5(7) . . ?
C6 C5 S2 117.7(6) . . ?
C4 C5 S2 121.7(6) . . ?
C1 C6 C5 122.0(8) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C12 C7 C8 120.0(8) . . ?
C12 C7 S2 119.0(6) . . ?
C8 C7 S2 121.0(7) . . ?
C9 C8 C7 118.9(8) . . ?
C9 C8 N1 119.0(8) . . ?
C7 C8 N1 121.9(8) . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.5(9) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 117.5(8) . . ?
C12 C11 C20 122.4(9) . . ?
C10 C11 C20 120.1(9) . . ?
C11 C12 C7 122.5(8) . . ?
C11 C12 H12 118.8 . . ?
C7 C12 H12 118.8 . . ?
C18 C13 C14 119.4(7) . . ?
C18 C13 N1 119.6(7) . . ?
C14 C13 N1 121.0(7) . . ?
C15 C14 C13 119.6(8) . . ?
C15 C14 S1 117.4(6) . . ?
C13 C14 S1 123.0(6) . . ?
C16 C15 C14 120.7(8) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.2(8) . . ?
C15 C16 C21 118.7(9) . . ?
C17 C16 C21 122.1(9) . . ?
C16 C17 C18 121.4(9) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 119.6(8) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.928
_diffrn_reflns_theta_full        71.50
_diffrn_measured_fraction_theta_full 0.927
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.520
_refine_diff_density_rms         0.124


