# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Thomas Muller'
_publ_contact_author_email       THOMASJJ.MUELLER@UNI-DUESSELDORF.DE

_publ_section_title              
;
First synthesis and electronic properties
in diphenothiazine dumbbells bridged by heterocycles
;
loop_
_publ_author_name
T.Muller
'Adam W. Franz'
'Larisa N. Popa'
'Frank Rominger'

# Attachment 'B814850C_CIF.cif'

data_afr8
_database_code_depnum_ccdc_archive 'CCDC 689758'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 N2 S3'
_chemical_formula_weight         478.62

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'
S S 0.1246 0.1234 '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                   8.3982(15)
_cell_length_b                   8.7381(16)
_cell_length_c                   17.245(3)
_cell_angle_alpha                83.601(5)
_cell_angle_beta                 87.923(4)
_cell_angle_gamma                62.354(4)
_cell_volume                     1113.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1866
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11772
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         28.32
_reflns_number_total             5501
_reflns_number_gt                4126
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0519P)^2^+0.3433P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5501
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
S1 S 0.69546(9) 0.78761(9) 0.22494(4) 0.02924(18) Uani 1 1 d . . .
C2 C 0.8372(4) 0.8725(4) 0.19039(17) 0.0293(6) Uani 1 1 d . . .
C3 C 0.8089(4) 1.0133(4) 0.22624(19) 0.0385(7) Uani 1 1 d . . .
H3 H 0.8724 1.0787 0.2142 0.046 Uiso 1 1 calc R . .
C4 C 0.6743(4) 1.0523(4) 0.28345(19) 0.0363(7) Uani 1 1 d . . .
H4 H 0.6390 1.1458 0.3144 0.044 Uiso 1 1 calc R . .
C5 C 0.6016(4) 0.9427(4) 0.28930(17) 0.0294(6) Uani 1 1 d . . .
N2 N 0.9582(3) 0.7935(3) 0.13144(14) 0.0313(6) Uani 1 1 d . . .
S2 S 1.17414(12) 0.54756(12) 0.01338(5) 0.0457(2) Uani 1 1 d . . .
N3 N 0.4721(3) 0.9344(3) 0.34210(14) 0.0298(5) Uani 1 1 d . . .
S3 S 0.21065(11) 0.83182(10) 0.42564(5) 0.0361(2) Uani 1 1 d . . .
C11 C 0.8957(4) 0.8524(4) 0.05262(18) 0.0320(7) Uani 1 1 d . . .
C12 C 0.7383(4) 1.0063(4) 0.0342(2) 0.0421(8) Uani 1 1 d . . .
H12 H 0.6743 1.0760 0.0743 0.051 Uiso 1 1 calc R . .
C13 C 0.6743(5) 1.0584(5) -0.0418(2) 0.0488(9) Uani 1 1 d . . .
H13 H 0.5652 1.1620 -0.0534 0.059 Uiso 1 1 calc R . .
C14 C 0.7671(6) 0.9617(5) -0.1006(2) 0.0547(10) Uani 1 1 d . . .
H14 H 0.7227 0.9983 -0.1529 0.066 Uiso 1 1 calc R . .
C15 C 0.9254(5) 0.8108(5) -0.0839(2) 0.0496(9) Uani 1 1 d . . .
H15 H 0.9913 0.7451 -0.1248 0.060 Uiso 1 1 calc R . .
C16 C 0.9890(4) 0.7546(4) -0.00729(19) 0.0364(7) Uani 1 1 d . . .
C17 C 1.2582(4) 0.5786(4) 0.09884(18) 0.0318(7) Uani 1 1 d . . .
C18 C 1.4401(4) 0.4816(4) 0.1163(2) 0.0388(8) Uani 1 1 d . . .
H18 H 1.5177 0.4092 0.0796 0.047 Uiso 1 1 calc R . .
C19 C 1.5102(4) 0.4883(4) 0.1860(2) 0.0406(8) Uani 1 1 d . . .
H19 H 1.6352 0.4214 0.1976 0.049 Uiso 1 1 calc R . .
C20 C 1.3966(4) 0.5933(4) 0.2384(2) 0.0383(7) Uani 1 1 d . . .
H20 H 1.4433 0.5966 0.2872 0.046 Uiso 1 1 calc R . .
C21 C 1.2158(4) 0.6943(4) 0.22149(18) 0.0345(7) Uani 1 1 d . . .
H21 H 1.1400 0.7677 0.2583 0.041 Uiso 1 1 calc R . .
C22 C 1.1433(4) 0.6897(4) 0.15106(17) 0.0291(6) Uani 1 1 d . . .
C31 C 0.2900(4) 1.0629(4) 0.33280(16) 0.0269(6) Uani 1 1 d . . .
C32 C 0.2382(4) 1.2174(4) 0.28459(17) 0.0332(7) Uani 1 1 d . . .
H32 H 0.3257 1.2369 0.2548 0.040 Uiso 1 1 calc R . .
C33 C 0.0601(4) 1.3430(4) 0.27979(18) 0.0374(7) Uani 1 1 d . . .
H33 H 0.0262 1.4471 0.2459 0.045 Uiso 1 1 calc R . .
C34 C -0.0687(4) 1.3191(4) 0.32350(19) 0.0395(8) Uani 1 1 d . . .
H34 H -0.1899 1.4078 0.3213 0.047 Uiso 1 1 calc R . .
C35 C -0.0200(4) 1.1651(4) 0.37043(18) 0.0354(7) Uani 1 1 d . . .
H35 H -0.1080 1.1473 0.4007 0.042 Uiso 1 1 calc R . .
C36 C 0.1575(4) 1.0360(4) 0.37353(16) 0.0282(6) Uani 1 1 d . . .
C37 C 0.4264(4) 0.7792(4) 0.46081(17) 0.0312(6) Uani 1 1 d . . .
C38 C 0.4898(5) 0.6789(4) 0.53188(18) 0.0393(8) Uani 1 1 d . . .
H38 H 0.4131 0.6455 0.5630 0.047 Uiso 1 1 calc R . .
C39 C 0.6616(5) 0.6273(4) 0.5578(2) 0.0456(9) Uani 1 1 d . . .
H39 H 0.7045 0.5568 0.6060 0.055 Uiso 1 1 calc R . .
C40 C 0.7715(5) 0.6789(4) 0.5130(2) 0.0470(9) Uani 1 1 d . . .
H40 H 0.8907 0.6434 0.5307 0.056 Uiso 1 1 calc R . .
C41 C 0.7099(4) 0.7816(4) 0.4429(2) 0.0401(8) Uani 1 1 d . . .
H41 H 0.7861 0.8181 0.4132 0.048 Uiso 1 1 calc R . .
C42 C 0.5368(4) 0.8321(4) 0.41559(17) 0.0300(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0250(4) 0.0264(4) 0.0355(4) -0.0044(3) 0.0054(3) -0.0113(3)
C2 0.0228(14) 0.0298(15) 0.0330(16) -0.0008(12) 0.0029(12) -0.0109(12)
C3 0.0341(17) 0.0358(17) 0.051(2) -0.0083(15) 0.0097(15) -0.0206(15)
C4 0.0312(16) 0.0301(16) 0.050(2) -0.0125(14) 0.0056(14) -0.0146(14)
C5 0.0239(14) 0.0289(15) 0.0321(16) -0.0056(12) 0.0053(12) -0.0093(12)
N2 0.0245(12) 0.0361(14) 0.0294(13) -0.0041(11) 0.0061(10) -0.0112(11)
S2 0.0396(5) 0.0499(5) 0.0497(5) -0.0228(4) 0.0064(4) -0.0193(4)
N3 0.0225(12) 0.0305(13) 0.0307(13) 0.0008(10) 0.0046(10) -0.0086(10)
S3 0.0365(4) 0.0369(4) 0.0367(4) -0.0010(3) 0.0060(3) -0.0195(4)
C11 0.0318(16) 0.0364(16) 0.0346(16) 0.0003(13) 0.0016(13) -0.0224(14)
C12 0.0417(19) 0.0349(17) 0.049(2) 0.0041(15) -0.0039(15) -0.0186(16)
C13 0.056(2) 0.0414(19) 0.054(2) 0.0163(17) -0.0163(18) -0.0304(18)
C14 0.074(3) 0.066(3) 0.040(2) 0.0148(19) -0.0132(19) -0.049(2)
C15 0.066(3) 0.067(3) 0.0365(19) -0.0026(17) 0.0029(17) -0.049(2)
C16 0.0359(17) 0.0443(18) 0.0382(18) -0.0028(14) 0.0037(14) -0.0268(15)
C17 0.0289(15) 0.0310(15) 0.0388(17) -0.0058(13) 0.0073(13) -0.0166(13)
C18 0.0290(16) 0.0287(16) 0.055(2) -0.0048(14) 0.0100(14) -0.0110(13)
C19 0.0257(16) 0.0354(17) 0.057(2) 0.0003(15) -0.0028(15) -0.0120(14)
C20 0.0337(17) 0.0393(18) 0.0426(19) 0.0009(14) -0.0037(14) -0.0183(15)
C21 0.0327(16) 0.0337(16) 0.0362(17) -0.0007(13) 0.0046(13) -0.0156(14)
C22 0.0253(14) 0.0280(15) 0.0363(17) -0.0005(12) 0.0051(12) -0.0153(12)
C31 0.0240(14) 0.0309(15) 0.0265(14) -0.0074(12) 0.0028(11) -0.0123(12)
C32 0.0289(15) 0.0336(16) 0.0333(16) -0.0002(13) 0.0023(12) -0.0123(13)
C33 0.0335(17) 0.0323(16) 0.0379(18) 0.0014(13) -0.0031(14) -0.0089(14)
C34 0.0254(16) 0.0422(18) 0.0416(18) -0.0044(15) -0.0060(13) -0.0074(14)
C35 0.0267(15) 0.0463(19) 0.0334(17) -0.0074(14) 0.0043(12) -0.0168(14)
C36 0.0292(15) 0.0310(15) 0.0249(14) -0.0041(12) 0.0021(12) -0.0141(13)
C37 0.0359(16) 0.0241(14) 0.0286(15) -0.0043(12) 0.0024(12) -0.0095(13)
C38 0.054(2) 0.0266(15) 0.0294(16) -0.0022(13) 0.0034(15) -0.0124(15)
C39 0.057(2) 0.0320(17) 0.0367(19) -0.0018(14) -0.0127(17) -0.0108(17)
C40 0.042(2) 0.0354(18) 0.053(2) -0.0076(16) -0.0152(17) -0.0072(16)
C41 0.0317(17) 0.0363(17) 0.046(2) -0.0064(15) -0.0014(14) -0.0096(14)
C42 0.0314(15) 0.0221(14) 0.0294(15) -0.0050(11) 0.0027(12) -0.0060(12)

_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
S1 C5 1.724(3) . ?
S1 C2 1.729(3) . ?
C2 C3 1.357(4) . ?
C2 N2 1.405(4) . ?
C3 C4 1.415(4) . ?
C4 C5 1.347(4) . ?
C5 N3 1.416(3) . ?
N2 C22 1.419(4) . ?
N2 C11 1.426(4) . ?
S2 C17 1.757(3) . ?
S2 C16 1.762(3) . ?
N3 C31 1.418(3) . ?
N3 C42 1.431(4) . ?
S3 C37 1.762(3) . ?
S3 C36 1.767(3) . ?
C11 C16 1.389(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.380(5) . ?
C13 C14 1.369(5) . ?
C14 C15 1.380(5) . ?
C15 C16 1.390(5) . ?
C17 C18 1.385(4) . ?
C17 C22 1.395(4) . ?
C18 C19 1.377(5) . ?
C19 C20 1.371(5) . ?
C20 C21 1.378(4) . ?
C21 C22 1.391(4) . ?
C31 C32 1.391(4) . ?
C31 C36 1.391(4) . ?
C32 C33 1.383(4) . ?
C33 C34 1.377(4) . ?
C34 C35 1.380(4) . ?
C35 C36 1.389(4) . ?
C37 C38 1.389(4) . ?
C37 C42 1.395(4) . ?
C38 C39 1.373(5) . ?
C39 C40 1.381(5) . ?
C40 C41 1.381(5) . ?
C41 C42 1.392(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
_geom_angle_publ_flag
C5 S1 C2 90.96(14) . . ?
C3 C2 N2 129.7(3) . . ?
C3 C2 S1 111.5(2) . . ?
N2 C2 S1 118.7(2) . . ?
C2 C3 C4 112.7(3) . . ?
C5 C4 C3 112.9(3) . . ?
C4 C5 N3 129.3(3) . . ?
C4 C5 S1 112.0(2) . . ?
N3 C5 S1 118.7(2) . . ?
C2 N2 C22 119.0(2) . . ?
C2 N2 C11 117.3(2) . . ?
C22 N2 C11 122.1(2) . . ?
C17 S2 C16 100.06(15) . . ?
C5 N3 C31 119.6(2) . . ?
C5 N3 C42 117.3(2) . . ?
C31 N3 C42 120.2(2) . . ?
C37 S3 C36 98.89(14) . . ?
C16 C11 C12 118.6(3) . . ?
C16 C11 N2 120.3(3) . . ?
C12 C11 N2 121.0(3) . . ?
C13 C12 C11 120.7(3) . . ?
C14 C13 C12 120.4(4) . . ?
C13 C14 C15 119.8(3) . . ?
C14 C15 C16 120.3(4) . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 S2 120.7(2) . . ?
C15 C16 S2 118.9(3) . . ?
C18 C17 C22 120.2(3) . . ?
C18 C17 S2 118.6(2) . . ?
C22 C17 S2 121.0(2) . . ?
C19 C18 C17 121.0(3) . . ?
C20 C19 C18 118.8(3) . . ?
C19 C20 C21 121.2(3) . . ?
C20 C21 C22 120.6(3) . . ?
C21 C22 C17 118.1(3) . . ?
C21 C22 N2 122.1(3) . . ?
C17 C22 N2 119.8(3) . . ?
C32 C31 C36 118.3(3) . . ?
C32 C31 N3 122.2(3) . . ?
C36 C31 N3 119.5(3) . . ?
C33 C32 C31 120.4(3) . . ?
C34 C33 C32 120.8(3) . . ?
C33 C34 C35 119.4(3) . . ?
C34 C35 C36 120.1(3) . . ?
C35 C36 C31 120.8(3) . . ?
C35 C36 S3 118.8(2) . . ?
C31 C36 S3 120.2(2) . . ?
C38 C37 C42 119.9(3) . . ?
C38 C37 S3 120.2(3) . . ?
C42 C37 S3 119.9(2) . . ?
C39 C38 C37 121.0(3) . . ?
C38 C39 C40 119.3(3) . . ?
C41 C40 C39 120.6(3) . . ?
C40 C41 C42 120.4(3) . . ?
C41 C42 C37 118.8(3) . . ?
C41 C42 N3 121.3(3) . . ?
C37 C42 N3 119.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.068

#======================================================================

# End of Crystallographic Information File