# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2007


data_global

_journal_coden_Cambridge         1145

loop_
_publ_author_name
'W.G. Skene'
'Marie Bourgeaux'
'Stephane Dufresne'

_publ_contact_author_name        'W.G. Skene'
_publ_contact_author_address     
;
Department of Chemistry
University of Montreal
CP 6128
Succ Centre-Ville
Montreal
Quebec
H3C 3J7
CANADA
;

_publ_contact_author_email       W.SKENE@UMONTREAL.CA

_publ_requested_journal          'Journal of Materials Chemistry'

_publ_section_title              
;
Tunable spectroscopic and electrochemical properties
of conjugated push-push, push-pull and pull-pull thiopheno azomethines
;

# Attachment 'SKENE9.CIF'

data_skene9
_database_code_depnum_ccdc_archive 'CCDC 626758'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H36 N4 O4 S3'
_chemical_formula_weight         588.79
_chemical_compound_source        'Synthesized by the authors. See text'

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'

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

_cell_length_a                   10.5863(4)
_cell_length_b                   10.9741(4)
_cell_length_c                   14.5969(5)
_cell_angle_alpha                96.217(2)
_cell_angle_beta                 97.195(2)
_cell_angle_gamma                111.441(2)
_cell_volume                     1544.06(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10345
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      54.96

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.4500
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Platform diffractometer, equipped with a Bruker SMART 2K
Charged-Coupled Device (CCD) Area Detector using the program SMART and
normal focus sealed tube source graphite monochromated Cu-K\a radiation.
The crystal-to-detector distance was 4.908 cm, and the data collection
was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 9.0 degree
scan in 30 frames over four different parts of the reciprocal space
(120 frames total). One complete sphere of data was collected, to
better than 0.8\%A resolution. Upon completion of the data collection,
the first 101 frames were recollected in order to improve the decay
correction analysis.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS Smart 2K/Platform'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 5.5
_diffrn_standards_number         121
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        -0.02
_diffrn_reflns_number            18808
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_sigmaI/netI    0.0630
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         54.97
_reflns_number_total             3767
_reflns_number_gt                2540
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'

_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^)+(0.2000P)^2^+0.0000P] 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         3767
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.1054
_refine_ls_wR_factor_ref         0.3097
_refine_ls_wR_factor_gt          0.2912
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_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
S1 S 0.21066(19) -0.19110(19) -0.12355(13) 0.0340(7) Uani 1 1 d . . .
S2 S 0.4958(2) -0.00719(19) 0.24763(12) 0.0344(7) Uani 1 1 d . . .
S3 S 0.6813(2) 0.28336(19) 0.61612(13) 0.0366(7) Uani 1 1 d . . .
O1 O 0.1601(7) 0.1978(8) 0.1839(5) 0.083(2) Uani 1 1 d . . .
O2 O 0.2248(6) 0.1373(6) 0.0549(4) 0.0548(17) Uani 1 1 d . . .
O3 O 0.4135(6) 0.3867(6) 0.3394(4) 0.0569(17) Uani 1 1 d . . .
O4 O 0.3161(5) 0.2341(5) 0.4271(4) 0.0433(15) Uani 1 1 d . . .
N1 N 0.1460(7) -0.3170(6) -0.3020(4) 0.0393(17) Uani 1 1 d . . .
N2 N 0.3318(6) -0.0584(6) 0.0738(4) 0.0307(16) Uani 1 1 d . . .
N3 N 0.5531(6) 0.1565(6) 0.4218(4) 0.0319(16) Uani 1 1 d . . .
N4 N 0.8104(7) 0.3613(6) 0.7969(4) 0.0443(18) Uani 1 1 d . . .
C1 C 0.2304(8) -0.2912(7) -0.2180(5) 0.0333(19) Uani 1 1 d . . .
C2 C 0.3381(8) -0.3304(7) -0.1934(5) 0.0341(19) Uani 1 1 d . . .
H2 H 0.3638 -0.3866 -0.2348 0.041 Uiso 1 1 calc R . .
C3 C 0.4048(7) -0.2788(7) -0.1017(5) 0.0316(19) Uani 1 1 d . . .
H3 H 0.4825 -0.2950 -0.0749 0.038 Uiso 1 1 calc R . .
C4 C 0.3501(8) -0.2024(7) -0.0525(5) 0.0307(19) Uani 1 1 d . . .
C5 C 0.3964(8) -0.1284(7) 0.0406(5) 0.034(2) Uani 1 1 d . . .
H5 H 0.4752 -0.1306 0.0783 0.041 Uiso 1 1 calc R . .
C6 C 0.3767(7) 0.0143(7) 0.1617(5) 0.0305(19) Uani 1 1 d . . .
C7 C 0.3298(7) 0.1087(7) 0.1975(5) 0.0280(18) Uani 1 1 d . . .
C8 C 0.3868(7) 0.1622(7) 0.2951(5) 0.0288(18) Uani 1 1 d . . .
C9 C 0.4791(8) 0.1114(7) 0.3322(5) 0.0308(19) Uani 1 1 d . . .
C10 C 0.6296(8) 0.1014(7) 0.4596(5) 0.032(2) Uani 1 1 d . . .
H10 H 0.6374 0.0270 0.4248 0.039 Uiso 1 1 calc R . .
C11 C 0.7026(7) 0.1499(7) 0.5528(5) 0.0306(19) Uani 1 1 d . . .
C12 C 0.7881(7) 0.1072(8) 0.6063(5) 0.037(2) Uani 1 1 d . . .
H12 H 0.8121 0.0356 0.5836 0.044 Uiso 1 1 calc R . .
C13 C 0.8374(8) 0.1782(7) 0.6975(5) 0.035(2) Uani 1 1 d . . .
H13 H 0.8982 0.1606 0.7429 0.042 Uiso 1 1 calc R . .
C14 C 0.7878(8) 0.2757(8) 0.7136(5) 0.036(2) Uani 1 1 d . . .
C15 C 0.1629(8) -0.3984(8) -0.3812(5) 0.042(2) Uani 1 1 d . . .
H15A H 0.2613 -0.3852 -0.3757 0.051 Uiso 1 1 calc R . .
H15B H 0.1361 -0.3689 -0.4397 0.051 Uiso 1 1 calc R . .
C16 C 0.0775(8) -0.5440(8) -0.3873(5) 0.045(2) Uani 1 1 d . . .
H16A H 0.1035 -0.5738 -0.3295 0.067 Uiso 1 1 calc R . .
H16B H 0.0940 -0.5947 -0.4408 0.067 Uiso 1 1 calc R . .
H16C H -0.0204 -0.5582 -0.3956 0.067 Uiso 1 1 calc R . .
C17 C 0.0282(8) -0.2764(8) -0.3149(6) 0.046(2) Uani 1 1 d . . .
H17A H -0.0036 -0.2687 -0.2543 0.055 Uiso 1 1 calc R . .
H17B H -0.0486 -0.3461 -0.3599 0.055 Uiso 1 1 calc R . .
C18 C 0.0621(9) -0.1469(9) -0.3501(7) 0.060(3) Uani 1 1 d . . .
H18A H 0.1398 -0.0779 -0.3068 0.089 Uiso 1 1 calc R . .
H18B H -0.0184 -0.1223 -0.3543 0.089 Uiso 1 1 calc R . .
H18C H 0.0870 -0.1558 -0.4122 0.089 Uiso 1 1 calc R . .
C19 C 0.2284(9) 0.1503(8) 0.1476(6) 0.046(2) Uani 1 1 d . . .
C20 C 0.1294(13) 0.1744(12) -0.0007(6) 0.098(5) Uani 1 1 d . . .
H20A H 0.1500 0.2702 0.0174 0.118 Uiso 1 1 calc R . .
H20B H 0.0343 0.1233 0.0082 0.118 Uiso 1 1 calc R . .
C21 C 0.1435(17) 0.1445(15) -0.1015(8) 0.138(7) Uani 1 1 d . . .
H21A H 0.2411 0.1811 -0.1069 0.208 Uiso 1 1 calc R . .
H21B H 0.0930 0.1848 -0.1407 0.208 Uiso 1 1 calc R . .
H21C H 0.1053 0.0481 -0.1222 0.208 Uiso 1 1 calc R . .
C22 C 0.3714(8) 0.2731(8) 0.3524(5) 0.036(2) Uani 1 1 d . . .
C23 C 0.3325(10) 0.3379(8) 0.5038(6) 0.053(2) Uani 1 1 d . . .
H23A H 0.2732 0.3865 0.4862 0.064 Uiso 1 1 calc R . .
H23B H 0.4296 0.4018 0.5194 0.064 Uiso 1 1 calc R . .
C24 C 0.2915(10) 0.2718(9) 0.5858(6) 0.063(3) Uani 1 1 d . . .
H24A H 0.1941 0.2119 0.5704 0.094 Uiso 1 1 calc R . .
H24B H 0.3052 0.3394 0.6399 0.094 Uiso 1 1 calc R . .
H24C H 0.3482 0.2209 0.6008 0.094 Uiso 1 1 calc R . .
C25 C 0.8940(9) 0.3507(8) 0.8795(5) 0.044(2) Uani 1 1 d . . .
H25A H 0.8803 0.2564 0.8786 0.053 Uiso 1 1 calc R . .
H25B H 0.8623 0.3802 0.9357 0.053 Uiso 1 1 calc R . .
C26 C 1.0459(9) 0.4321(8) 0.8869(6) 0.056(3) Uani 1 1 d . . .
H26A H 1.0785 0.4024 0.8321 0.083 Uiso 1 1 calc R . .
H26B H 1.0971 0.4207 0.9439 0.083 Uiso 1 1 calc R . .
H26C H 1.0606 0.5261 0.8896 0.083 Uiso 1 1 calc R . .
C27 C 0.7573(10) 0.4675(8) 0.8021(6) 0.054(2) Uani 1 1 d . . .
H27A H 0.7437 0.4909 0.7390 0.064 Uiso 1 1 calc R . .
H27B H 0.8266 0.5474 0.8439 0.064 Uiso 1 1 calc R . .
C28 C 0.6237(10) 0.4292(9) 0.8378(6) 0.067(3) Uani 1 1 d . . .
H28A H 0.5516 0.3575 0.7925 0.100 Uiso 1 1 calc R . .
H28B H 0.5978 0.5062 0.8462 0.100 Uiso 1 1 calc R . .
H28C H 0.6344 0.3989 0.8979 0.100 Uiso 1 1 calc R . .

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 0.0440(13) 0.0482(13) 0.0249(12) 0.0110(9) 0.0143(9) 0.0311(10)
S2 0.0523(14) 0.0523(14) 0.0194(12) 0.0157(9) 0.0151(9) 0.0383(11)
S3 0.0522(14) 0.0517(13) 0.0222(12) 0.0154(9) 0.0116(9) 0.0345(11)
O1 0.088(5) 0.141(6) 0.050(4) -0.017(4) -0.006(4) 0.092(5)
O2 0.082(4) 0.078(4) 0.025(4) 0.006(3) -0.009(3) 0.062(4)
O3 0.086(5) 0.054(4) 0.041(4) 0.010(3) 0.016(3) 0.037(4)
O4 0.054(4) 0.052(4) 0.037(4) 0.004(3) 0.023(3) 0.032(3)
N1 0.045(4) 0.058(4) 0.026(4) 0.004(3) 0.011(3) 0.032(4)
N2 0.045(4) 0.046(4) 0.022(4) 0.016(3) 0.021(3) 0.034(3)
N3 0.043(4) 0.053(4) 0.016(4) 0.017(3) 0.014(3) 0.031(4)
N4 0.068(5) 0.052(4) 0.024(4) 0.006(3) 0.007(3) 0.036(4)
C1 0.038(5) 0.040(5) 0.030(5) 0.009(4) 0.014(4) 0.020(4)
C2 0.042(5) 0.043(5) 0.025(5) 0.003(4) 0.015(4) 0.025(4)
C3 0.037(5) 0.039(5) 0.035(5) 0.016(4) 0.015(4) 0.029(4)
C4 0.044(5) 0.035(4) 0.024(5) 0.011(3) 0.013(4) 0.025(4)
C5 0.043(5) 0.044(5) 0.024(5) 0.020(4) 0.012(4) 0.020(4)
C6 0.042(5) 0.037(5) 0.026(5) 0.016(4) 0.014(4) 0.024(4)
C7 0.033(4) 0.044(5) 0.017(4) 0.010(3) 0.006(3) 0.024(4)
C8 0.032(4) 0.037(4) 0.029(5) 0.011(3) 0.011(3) 0.024(4)
C9 0.043(5) 0.040(5) 0.022(5) 0.014(3) 0.018(4) 0.024(4)
C10 0.046(5) 0.043(5) 0.023(5) 0.011(4) 0.022(4) 0.027(4)
C11 0.037(5) 0.045(5) 0.026(5) 0.019(4) 0.012(4) 0.027(4)
C12 0.037(5) 0.052(5) 0.034(5) 0.016(4) 0.012(4) 0.026(4)
C13 0.046(5) 0.050(5) 0.023(5) 0.019(4) 0.009(4) 0.030(4)
C14 0.045(5) 0.044(5) 0.031(5) 0.023(4) 0.012(4) 0.026(4)
C15 0.039(5) 0.066(6) 0.029(5) 0.002(4) 0.014(4) 0.028(5)
C16 0.049(5) 0.072(6) 0.025(5) 0.005(4) 0.017(4) 0.033(5)
C17 0.045(5) 0.071(6) 0.035(5) 0.011(4) 0.013(4) 0.036(5)
C18 0.057(6) 0.091(7) 0.057(7) 0.026(5) 0.020(5) 0.052(6)
C19 0.054(6) 0.062(6) 0.035(6) -0.007(4) 0.003(4) 0.043(5)
C20 0.153(11) 0.141(10) 0.035(6) -0.025(6) -0.041(7) 0.126(9)
C21 0.250(17) 0.195(14) 0.042(8) -0.018(8) -0.039(9) 0.201(14)
C22 0.048(5) 0.040(5) 0.027(5) 0.010(4) 0.003(4) 0.026(4)
C23 0.073(7) 0.058(6) 0.035(6) 0.000(4) 0.016(5) 0.032(5)
C24 0.086(7) 0.081(7) 0.043(6) 0.010(5) 0.027(5) 0.052(6)
C25 0.071(7) 0.050(5) 0.018(5) 0.014(4) 0.007(4) 0.030(5)
C26 0.071(7) 0.051(6) 0.040(6) 0.019(4) -0.002(5) 0.018(5)
C27 0.090(7) 0.061(6) 0.033(5) 0.010(4) 0.015(5) 0.052(6)
C28 0.109(9) 0.090(7) 0.046(6) 0.032(5) 0.036(6) 0.075(7)

_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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 . . 1.745(8) Y
S1 C1 . . 1.751(8) Y
S2 C6 . . 1.762(7) Y
S2 C9 . . 1.767(7) Y
S3 C14 . . 1.731(8) Y
S3 C11 . . 1.746(8) Y
O1 C19 . . 1.178(9) Y
O2 C19 . . 1.341(10) Y
O2 C20 . . 1.417(10) Y
O3 C22 . . 1.205(9) Y
O4 C22 . . 1.339(9) Y
O4 C23 . . 1.453(9) Y
N1 C1 . . 1.359(10) Y
N1 C15 . . 1.452(10) Y
N1 C17 . . 1.469(10) Y
N2 C5 . . 1.295(9) Y
N2 C6 . . 1.362(9) Y
N3 C10 . . 1.282(9) Y
N3 C9 . . 1.374(9) Y
N4 C14 . . 1.391(10) Y
N4 C25 . . 1.444(10) Y
N4 C27 . . 1.467(10) Y
C1 C2 . . 1.380(11) Y
C2 C3 . . 1.384(10) Y
C2 H2 . . 0.95 ?
C3 C4 . . 1.373(10) Y
C3 H3 . . 0.95 ?
C4 C5 . . 1.432(10) Y
C5 H5 . . 0.95 ?
C6 C7 . . 1.384(10) Y
C7 C8 . . 1.443(10) Y
C7 C19 . . 1.458(11) Y
C8 C9 . . 1.375(10) Y
C8 C22 . . 1.472(11) Y
C10 C11 . . 1.418(10) Y
C10 H10 . . 0.95 ?
C11 C12 . . 1.364(10) Y
C12 C13 . . 1.398(10) Y
C12 H12 . . 0.95 ?
C13 C14 . . 1.365(10) Y
C13 H13 . . 0.95 ?
C15 C16 . . 1.507(11) Y
C15 H15a . . 0.99 ?
C15 H15b . . 0.99 ?
C16 H16a . . 0.98 ?
C16 H16b . . 0.98 ?
C16 H16c . . 0.98 ?
C17 C18 . . 1.498(11) Y
C17 H17a . . 0.99 ?
C17 H17b . . 0.99 ?
C18 H18a . . 0.98 ?
C18 H18b . . 0.98 ?
C18 H18c . . 0.98 ?
C20 C21 . . 1.510(16) Y
C20 H20a . . 0.99 ?
C20 H20b . . 0.99 ?
C21 H21a . . 0.98 ?
C21 H21b . . 0.98 ?
C21 H21c . . 0.98 ?
C23 C24 . . 1.495(12) Y
C23 H23a . . 0.99 ?
C23 H23b . . 0.99 ?
C24 H24a . . 0.98 ?
C24 H24b . . 0.98 ?
C24 H24c . . 0.98 ?
C25 C26 . . 1.510(12) Y
C25 H25a . . 0.99 ?
C25 H25b . . 0.99 ?
C26 H26a . . 0.98 ?
C26 H26b . . 0.98 ?
C26 H26c . . 0.98 ?
C27 C28 . . 1.498(12) Y
C27 H27a . . 0.99 ?
C27 H27b . . 0.99 ?
C28 H28a . . 0.98 ?
C28 H28b . . 0.98 ?
C28 H28c . . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 S1 C1 . . . 90.9(4) Y
C6 S2 C9 . . . 91.7(4) Y
C14 S3 C11 . . . 90.4(4) Y
C19 O2 C20 . . . 118.4(7) Y
C22 O4 C23 . . . 116.9(6) Y
C1 N1 C15 . . . 119.8(6) Y
C1 N1 C17 . . . 122.6(6) Y
C15 N1 C17 . . . 117.3(6) Y
C5 N2 C6 . . . 121.0(7) Y
C10 N3 C9 . . . 122.8(7) Y
C14 N4 C25 . . . 119.7(6) Y
C14 N4 C27 . . . 121.5(7) Y
C25 N4 C27 . . . 118.7(6) Y
N1 C1 C2 . . . 129.5(7) Y
N1 C1 S1 . . . 119.4(6) Y
C2 C1 S1 . . . 111.1(6) Y
C1 C2 C3 . . . 112.7(7) Y
C1 C2 H2 . . . 123.7 ?
C3 C2 H2 . . . 123.7 ?
C4 C3 C2 . . . 114.8(7) Y
C4 C3 H3 . . . 122.6 ?
C2 C3 H3 . . . 122.6 ?
C3 C4 C5 . . . 129.9(7) Y
C3 C4 S1 . . . 110.4(6) Y
C5 C4 S1 . . . 119.5(6) Y
N2 C5 C4 . . . 120.6(7) Y
N2 C5 H5 . . . 119.7 ?
C4 C5 H5 . . . 119.7 ?
N2 C6 C7 . . . 125.2(7) Y
N2 C6 S2 . . . 123.9(6) Y
C7 C6 S2 . . . 110.8(5) Y
C6 C7 C8 . . . 113.2(6) Y
C6 C7 C19 . . . 126.3(7) Y
C8 C7 C19 . . . 120.4(7) Y
C9 C8 C7 . . . 113.3(7) Y
C9 C8 C22 . . . 118.5(7) Y
C7 C8 C22 . . . 127.7(7) Y
N3 C9 C8 . . . 122.6(7) Y
N3 C9 S2 . . . 126.2(6) Y
C8 C9 S2 . . . 111.0(6) Y
N3 C10 C11 . . . 121.0(7) Y
N3 C10 H10 . . . 119.5 ?
C11 C10 H10 . . . 119.5 ?
C12 C11 C10 . . . 130.8(7) Y
C12 C11 S3 . . . 111.0(6) Y
C10 C11 S3 . . . 118.2(5) Y
C11 C12 C13 . . . 114.1(7) Y
C11 C12 H12 . . . 123 ?
C13 C12 H12 . . . 123 ?
C14 C13 C12 . . . 112.0(7) Y
C14 C13 H13 . . . 124 ?
C12 C13 H13 . . . 124 ?
C13 C14 N4 . . . 127.7(7) Y
C13 C14 S3 . . . 112.6(6) Y
N4 C14 S3 . . . 119.7(6) Y
N1 C15 C16 . . . 112.6(6) Y
N1 C15 H15A . . . 109.1 ?
C16 C15 H15A . . . 109.1 ?
N1 C15 H15B . . . 109.1 ?
C16 C15 H15B . . . 109.1 ?
H15A C15 H15B . . . 107.8 ?
C15 C16 H16A . . . 109.5 ?
C15 C16 H16B . . . 109.5 ?
H16A C16 H16B . . . 109.5 ?
C15 C16 H16C . . . 109.5 ?
H16A C16 H16C . . . 109.5 ?
H16B C16 H16C . . . 109.5 ?
N1 C17 C18 . . . 112.8(7) Y
N1 C17 H17A . . . 109 ?
C18 C17 H17A . . . 109 ?
N1 C17 H17B . . . 109 ?
C18 C17 H17B . . . 109 ?
H17A C17 H17B . . . 107.8 ?
C17 C18 H18A . . . 109.5 ?
C17 C18 H18B . . . 109.5 ?
H18A C18 H18B . . . 109.5 ?
C17 C18 H18C . . . 109.5 ?
H18A C18 H18C . . . 109.5 ?
H18B C18 H18C . . . 109.5 ?
O1 C19 O2 . . . 121.7(8) Y
O1 C19 C7 . . . 124.6(8) Y
O2 C19 C7 . . . 113.6(7) Y
O2 C20 C21 . . . 107.2(8) Y
O2 C20 H20A . . . 110.3 ?
C21 C20 H20A . . . 110.3 ?
O2 C20 H20B . . . 110.3 ?
C21 C20 H20B . . . 110.3 ?
H20A C20 H20B . . . 108.5 ?
C20 C21 H21A . . . 109.5 ?
C20 C21 H21B . . . 109.5 ?
H21A C21 H21B . . . 109.5 ?
C20 C21 H21C . . . 109.5 ?
H21A C21 H21C . . . 109.5 ?
H21B C21 H21C . . . 109.5 ?
O3 C22 O4 . . . 123.6(7) Y
O3 C22 C8 . . . 125.2(8) Y
O4 C22 C8 . . . 110.8(7) Y
O4 C23 C24 . . . 107.2(7) Y
O4 C23 H23A . . . 110.3 ?
C24 C23 H23A . . . 110.3 ?
O4 C23 H23B . . . 110.3 ?
C24 C23 H23B . . . 110.3 ?
H23A C23 H23B . . . 108.5 ?
C23 C24 H24A . . . 109.5 ?
C23 C24 H24B . . . 109.5 ?
H24A C24 H24B . . . 109.5 ?
C23 C24 H24C . . . 109.5 ?
H24A C24 H24C . . . 109.5 ?
H24B C24 H24C . . . 109.5 ?
N4 C25 C26 . . . 113.2(6) Y
N4 C25 H25A . . . 108.9 ?
C26 C25 H25A . . . 108.9 ?
N4 C25 H25B . . . 108.9 ?
C26 C25 H25B . . . 108.9 ?
H25A C25 H25B . . . 107.8 ?
C25 C26 H26A . . . 109.5 ?
C25 C26 H26B . . . 109.5 ?
H26A C26 H26B . . . 109.5 ?
C25 C26 H26C . . . 109.5 ?
H26A C26 H26C . . . 109.5 ?
H26B C26 H26C . . . 109.5 ?
N4 C27 C28 . . . 112.7(7) Y
N4 C27 H27A . . . 109 ?
C28 C27 H27A . . . 109 ?
N4 C27 H27B . . . 109 ?
C28 C27 H27B . . . 109 ?
H27A C27 H27B . . . 107.8 ?
C27 C28 H28A . . . 109.5 ?
C27 C28 H28B . . . 109.5 ?
H28A C28 H28B . . . 109.5 ?
C27 C28 H28C . . . 109.5 ?
H28A C28 H28C . . . 109.5 ?
H28B C28 H28C . . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 N1 C1 C2 . . . . 0.90(12) Y
C17 N1 C1 C2 . . . . 175.0(8) Y
C15 N1 C1 S1 . . . . 179.1(5) Y
C17 N1 C1 S1 . . . . -6.8(1) Y
C4 S1 C1 N1 . . . . -177.9(6) Y
C4 S1 C1 C2 . . . . 0.6(6) Y
N1 C1 C2 C3 . . . . 177.0(7) Y
S1 C1 C2 C3 . . . . -1.3(8) Y
C1 C2 C3 C4 . . . . 1.6(9) Y
C2 C3 C4 C5 . . . . -176.1(7) Y
C2 C3 C4 S1 . . . . -1.0(8) Y
C1 S1 C4 C3 . . . . 0.2(6) Y
C1 S1 C4 C5 . . . . 175.9(6) Y
C6 N2 C5 C4 . . . . -178.7(6) Y
C3 C4 C5 N2 . . . . 177.9(7) Y
S1 C4 C5 N2 . . . . 3.3(1) Y
C5 N2 C6 C7 . . . . 168.6(7) Y
C5 N2 C6 S2 . . . . -15.6(1) Y
C9 S2 C6 N2 . . . . -175.8(6) Y
C9 S2 C6 C7 . . . . 0.6(6) Y
N2 C6 C7 C8 . . . . 175.0(6) Y
S2 C6 C7 C8 . . . . -1.3(8) Y
N2 C6 C7 C19 . . . . -2.20(12) Y
S2 C6 C7 C19 . . . . -178.5(6) Y
C6 C7 C8 C9 . . . . 1.6(9) Y
C19 C7 C8 C9 . . . . 178.9(7) Y
C6 C7 C8 C22 . . . . 173.0(7) Y
C19 C7 C8 C22 . . . . -9.70(12) Y
C10 N3 C9 C8 . . . . 173.4(7) Y
C10 N3 C9 S2 . . . . -11.3(1) Y
C7 C8 C9 N3 . . . . 174.9(6) Y
C22 C8 C9 N3 . . . . 2.60(11) Y
C7 C8 C9 S2 . . . . -1.1(8) Y
C22 C8 C9 S2 . . . . -173.3(6) Y
C6 S2 C9 N3 . . . . -175.5(6) Y
C6 S2 C9 C8 . . . . 0.3(6) Y
C9 N3 C10 C11 . . . . -179.0(6) Y
N3 C10 C11 C12 . . . . 179.8(7) Y
N3 C10 C11 S3 . . . . 2.1(1) Y
C14 S3 C11 C12 . . . . -0.6(6) Y
C14 S3 C11 C10 . . . . 177.6(6) Y
C10 C11 C12 C13 . . . . -177.6(7) Y
S3 C11 C12 C13 . . . . 0.2(8) Y
C11 C12 C13 C14 . . . . 0.4(9) Y
C12 C13 C14 N4 . . . . 177.1(7) Y
C12 C13 C14 S3 . . . . -0.8(8) Y
C25 N4 C14 C13 . . . . -0.80(12) Y
C27 N4 C14 C13 . . . . 176.0(8) Y
C25 N4 C14 S3 . . . . 177.1(6) Y
C27 N4 C14 S3 . . . . -6.2(1) Y
C11 S3 C14 C13 . . . . 0.8(6) Y
C11 S3 C14 N4 . . . . -177.3(6) Y
C1 N1 C15 C16 . . . . 90.0(9) Y
C17 N1 C15 C16 . . . . -84.4(9) Y
C1 N1 C17 C18 . . . . 95.5(9) Y
C15 N1 C17 C18 . . . . -90.3(9) Y
C20 O2 C19 O1 . . . . -4.10(13) Y
C20 O2 C19 C7 . . . . 179.8(8) Y
C6 C7 C19 O1 . . . . 156.0(9) Y
C8 C7 C19 O1 . . . . -21.00(13) Y
C6 C7 C19 O2 . . . . -27.90(12) Y
C8 C7 C19 O2 . . . . 155.1(7) Y
C19 O2 C20 C21 . . . . -177.7(1) Y
C23 O4 C22 O3 . . . . -12.00(11) Y
C23 O4 C22 C8 . . . . 161.9(6) Y
C9 C8 C22 O3 . . . . 107.2(9) Y
C7 C8 C22 O3 . . . . -63.80(12) Y
C9 C8 C22 O4 . . . . -66.6(9) Y
C7 C8 C22 O4 . . . . 122.4(8) Y
C22 O4 C23 C24 . . . . -167.8(7) Y
C14 N4 C25 C26 . . . . 87.9(9) Y
C27 N4 C25 C26 . . . . -88.9(9) Y
C14 N4 C27 C28 . . . . 97.1(9) Y
C25 N4 C27 C28 . . . . -86.1(9) Y

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        54.97
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.705
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.163