# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_address             ' Yasushi Morita '
_publ_author_footnote            ?
_publ_contact_author_email       morita@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5395
_publ_contact_author_phone       +81-6-6850-5393

_publ_contact_author_name        'Yasushi Morita'
_publ_contact_letter             
;
ENTER TEXT OF LETTER
;
_publ_requested_category         'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name    ?

_publ_section_title              ?
loop_
_publ_author_name
T.Murata
Y.Morita

data_TTF-PhU_THF
_database_code_depnum_ccdc_archive 'CCDC 826938'
#TrackingRef '- CIF.cif'

_audit_creation_method           SHELXL-97
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;

#Assistant Professor

#Department of Chemistry, Graduate School of Science, Osaka University
#Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan

_chemical_name_systematic        
;
?
;
_chemical_name_common            TTFPhU-THF
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.96 H15.92 N2 O2.74 S4'
_chemical_formula_weight         443.90

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'
O O 0.0106 0.0060 '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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   18.863(8)
_cell_length_b                   5.722(3)
_cell_length_c                   21.510(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.96(3)
_cell_angle_gamma                90.00
_cell_volume                     2069.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10935
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.50

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             918.5
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7454
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   '(Higashi, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoKa
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \^A\/Yw
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15488
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4269
_reflns_number_gt                2597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID AUTO'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'

_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. The site-occupancy factor
of THF solvent was refined, and a global Uiso was applied for O3 and
C17\^a C20 atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\^A\/Ys^2^(Fo^2^)+(0.1364P)^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         4269
_refine_ls_number_parameters     234
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2219
_refine_ls_wR_factor_gt          0.2030
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.029
_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 0.25612(7) 0.9552(2) 0.07646(6) 0.0386(3) Uani 1 1 d . . .
S2 S 0.25235(8) 1.0974(3) 0.20621(7) 0.0485(4) Uani 1 1 d . . .
S3 S 0.37797(8) 1.5087(3) 0.22964(9) 0.0634(5) Uani 1 1 d . . .
S4 S 0.38830(10) 1.3626(3) 0.10207(9) 0.0698(5) Uani 1 1 d . . .
O1 O 0.0330(2) 0.0438(5) -0.06556(16) 0.0372(7) Uani 1 1 d . . .
O2 O 0.0826(2) 0.4853(6) 0.12431(16) 0.0418(8) Uani 1 1 d . . .
O3 O 0.2872(5) 0.7439(16) 0.4365(4) 0.117(2) Uiso 0.740(10) 1 d PD . .
N1 N 0.1104(2) 0.3715(6) -0.04748(17) 0.0285(8) Uani 1 1 d . . .
N2 N 0.0632(2) 0.2671(6) 0.03083(17) 0.0312(8) Uani 1 1 d . . .
H2 H 0.0359 0.1695 0.0433 0.037 Uiso 1 1 calc R . .
C1 C 0.3451(3) 1.3142(9) 0.1586(3) 0.0441(11) Uani 1 1 d . . .
C2 C 0.4414(4) 1.6136(13) 0.1486(4) 0.081(2) Uani 1 1 d . . .
H2A H 0.4723 1.7030 0.1326 0.097 Uiso 1 1 calc R . .
C3 C 0.4367(4) 1.6713(12) 0.2047(4) 0.074(2) Uani 1 1 d . . .
H3 H 0.4655 1.8018 0.2316 0.089 Uiso 1 1 calc R . .
C4 C 0.2926(3) 1.1454(8) 0.1481(2) 0.0356(10) Uani 1 1 d . . .
C5 C 0.1927(2) 0.7958(8) 0.1010(2) 0.0312(9) Uani 1 1 d . . .
C6 C 0.1925(3) 0.8663(9) 0.1605(2) 0.0404(11) Uani 1 1 d . . .
H6 H 0.1599 0.7898 0.1772 0.049 Uiso 1 1 calc R . .
C7 C 0.1474(2) 0.6027(7) 0.0560(2) 0.0281(9) Uani 1 1 d . . .
C8 C 0.0972(3) 0.4552(7) 0.0753(2) 0.0309(9) Uani 1 1 d . . .
C9 C 0.0665(2) 0.2127(8) -0.0302(2) 0.0301(9) Uani 1 1 d . . .
C10 C 0.1504(2) 0.5535(7) -0.0044(2) 0.0290(9) Uani 1 1 d . . .
H10 H 0.1821 0.6508 -0.0177 0.035 Uiso 1 1 calc R . .
C11 C 0.1075(2) 0.3567(7) -0.1163(2) 0.0278(9) Uani 1 1 d . . .
C12 C 0.1388(3) 0.1660(8) -0.1341(2) 0.0361(10) Uani 1 1 d . . .
H12 H 0.1624 0.0419 -0.1020 0.043 Uiso 1 1 calc R . .
C13 C 0.1351(3) 0.1585(9) -0.2001(3) 0.0433(12) Uani 1 1 d . . .
H13 H 0.1552 0.0264 -0.2138 0.052 Uiso 1 1 calc R . .
C14 C 0.1023(3) 0.3421(9) -0.2459(2) 0.0396(11) Uani 1 1 d . . .
H14 H 0.1004 0.3362 -0.2908 0.048 Uiso 1 1 calc R . .
C15 C 0.0721(3) 0.5351(8) -0.2269(2) 0.0347(10) Uani 1 1 d . . .
H15 H 0.0497 0.6614 -0.2585 0.042 Uiso 1 1 calc R . .
C16 C 0.0749(3) 0.5421(8) -0.1610(2) 0.0312(9) Uani 1 1 d . . .
H16 H 0.0547 0.6734 -0.1472 0.037 Uiso 1 1 calc R . .
C17 C 0.3008(8) 0.895(2) 0.3951(7) 0.117(2) Uiso 0.740(10) 1 d PD . .
H17A H 0.2924 1.0548 0.4079 0.140 Uiso 0.740(10) 1 calc PR . .
H17B H 0.2599 0.8672 0.3465 0.140 Uiso 0.740(10) 1 calc PR . .
C18 C 0.3798(8) 0.888(2) 0.3960(7) 0.117(2) Uiso 0.740(10) 1 d PD . .
H18A H 0.4143 1.0172 0.4241 0.140 Uiso 0.740(10) 1 calc PR . .
H18B H 0.3751 0.8943 0.3482 0.140 Uiso 0.740(10) 1 calc PR . .
C19 C 0.4097(8) 0.655(2) 0.4295(7) 0.117(2) Uiso 0.740(10) 1 d PD . .
H19A H 0.4639 0.6686 0.4686 0.140 Uiso 0.740(10) 1 calc PR . .
H19B H 0.4103 0.5406 0.3953 0.140 Uiso 0.740(10) 1 calc PR . .
C20 C 0.3504(8) 0.586(2) 0.4555(7) 0.117(2) Uiso 0.740(10) 1 d PD . .
H20A H 0.3287 0.4295 0.4366 0.140 Uiso 0.740(10) 1 calc PR . .
H20B H 0.3783 0.5732 0.5070 0.140 Uiso 0.740(10) 1 calc PR . .

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 0.0389(6) 0.0439(7) 0.0379(6) -0.0080(5) 0.0217(5) -0.0119(5)
S2 0.0509(7) 0.0555(9) 0.0444(7) -0.0169(6) 0.0263(6) -0.0067(6)
S3 0.0426(7) 0.0527(9) 0.0770(10) -0.0260(8) 0.0115(7) -0.0005(7)
S4 0.0672(10) 0.0679(11) 0.0827(11) -0.0064(9) 0.0413(9) -0.0275(9)
O1 0.0465(17) 0.0296(17) 0.0439(17) -0.0006(15) 0.0278(15) -0.0078(15)
O2 0.055(2) 0.0448(19) 0.0401(17) 0.0016(15) 0.0343(16) -0.0023(16)
N1 0.0328(17) 0.0290(19) 0.0278(17) 0.0028(15) 0.0174(15) -0.0022(16)
N2 0.0366(19) 0.0289(19) 0.0348(18) 0.0097(16) 0.0220(16) -0.0010(16)
C1 0.032(2) 0.040(3) 0.052(3) -0.006(2) 0.012(2) 0.001(2)
C2 0.052(4) 0.059(4) 0.111(6) 0.009(4) 0.017(4) -0.025(3)
C3 0.050(3) 0.043(4) 0.096(5) -0.006(4) 0.005(4) -0.010(3)
C4 0.029(2) 0.036(3) 0.038(2) -0.005(2) 0.0121(19) 0.003(2)
C5 0.031(2) 0.033(2) 0.033(2) 0.0052(19) 0.0163(18) 0.0041(19)
C6 0.043(3) 0.045(3) 0.039(2) -0.001(2) 0.024(2) -0.001(2)
C7 0.0257(19) 0.029(2) 0.031(2) 0.0032(18) 0.0140(17) -0.0003(17)
C8 0.032(2) 0.028(2) 0.035(2) 0.0083(19) 0.0177(19) 0.0061(18)
C9 0.032(2) 0.027(2) 0.035(2) 0.0069(19) 0.0183(19) 0.0018(18)
C10 0.031(2) 0.026(2) 0.032(2) 0.0024(18) 0.0159(18) -0.0029(18)
C11 0.0287(19) 0.031(2) 0.028(2) 0.0009(18) 0.0167(17) -0.0042(17)
C12 0.043(2) 0.030(2) 0.043(2) 0.002(2) 0.025(2) 0.001(2)
C13 0.052(3) 0.038(3) 0.053(3) -0.013(2) 0.035(2) -0.008(2)
C14 0.046(3) 0.046(3) 0.036(2) -0.008(2) 0.027(2) -0.013(2)
C15 0.038(2) 0.038(3) 0.031(2) 0.0026(19) 0.0189(19) -0.003(2)
C16 0.035(2) 0.031(2) 0.032(2) 0.0004(18) 0.0192(19) -0.0002(19)

_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 C4 1.753(5) . ?
S1 C5 1.766(4) . ?
S2 C6 1.727(5) . ?
S2 C4 1.754(5) . ?
S3 C3 1.709(8) . ?
S3 C1 1.760(5) . ?
S4 C1 1.766(5) . ?
S4 C2 1.778(7) . ?
O1 C9 1.215(5) . ?
O2 C8 1.217(5) . ?
O3 C17 1.346(11) . ?
O3 C20 1.402(12) . ?
N1 C10 1.370(5) . ?
N1 C9 1.390(5) . ?
N1 C11 1.459(5) . ?
N2 C9 1.377(5) . ?
N2 C8 1.388(6) . ?
N2 H2 0.8800 . ?
C1 C4 1.327(7) . ?
C2 C3 1.292(10) . ?
C2 H2A 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.341(6) . ?
C5 C7 1.462(6) . ?
C6 H6 0.9500 . ?
C7 C10 1.357(5) . ?
C7 C8 1.462(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(6) . ?
C11 C16 1.375(6) . ?
C12 C13 1.390(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.482(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.498(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.512(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 S1 C5 96.1(2) . . ?
C6 S2 C4 95.5(2) . . ?
C3 S3 C1 95.4(3) . . ?
C1 S4 C2 93.3(3) . . ?
C17 O3 C20 102.5(10) . . ?
C10 N1 C9 121.9(3) . . ?
C10 N1 C11 119.1(3) . . ?
C9 N1 C11 118.8(3) . . ?
C9 N2 C8 128.7(3) . . ?
C9 N2 H2 115.6 . . ?
C8 N2 H2 115.6 . . ?
C4 C1 S3 123.3(4) . . ?
C4 C1 S4 122.6(4) . . ?
S3 C1 S4 114.1(3) . . ?
C3 C2 S4 118.2(6) . . ?
C3 C2 H2A 120.9 . . ?
S4 C2 H2A 120.9 . . ?
C2 C3 S3 118.9(5) . . ?
C2 C3 H3 120.6 . . ?
S3 C3 H3 120.6 . . ?
C1 C4 S1 124.5(4) . . ?
C1 C4 S2 121.6(4) . . ?
S1 C4 S2 113.9(3) . . ?
C6 C5 C7 127.3(4) . . ?
C6 C5 S1 115.1(4) . . ?
C7 C5 S1 117.6(3) . . ?
C5 C6 S2 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
S2 C6 H6 120.3 . . ?
C10 C7 C8 117.8(4) . . ?
C10 C7 C5 121.7(4) . . ?
C8 C7 C5 120.5(4) . . ?
O2 C8 N2 119.4(4) . . ?
O2 C8 C7 126.5(4) . . ?
N2 C8 C7 114.1(3) . . ?
O1 C9 N2 122.8(4) . . ?
O1 C9 N1 123.7(4) . . ?
N2 C9 N1 113.4(4) . . ?
C7 C10 N1 123.7(4) . . ?
C7 C10 H10 118.1 . . ?
N1 C10 H10 118.1 . . ?
C12 C11 C16 121.9(4) . . ?
C12 C11 N1 120.3(4) . . ?
C16 C11 N1 117.7(4) . . ?
C11 C12 C13 118.7(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.4(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 119.2(4) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O3 C17 C18 117.8(12) . . ?
O3 C17 H17A 107.8 . . ?
C18 C17 H17A 107.8 . . ?
O3 C17 H17B 107.8 . . ?
C18 C17 H17B 107.8 . . ?
H17A C17 H17B 107.2 . . ?
C17 C18 C19 100.7(11) . . ?
C17 C18 H18A 111.6 . . ?
C19 C18 H18A 111.6 . . ?
C17 C18 H18B 111.6 . . ?
C19 C18 H18B 111.6 . . ?
H18A C18 H18B 109.4 . . ?
C18 C19 C20 103.4(11) . . ?
C18 C19 H19A 111.1 . . ?
C20 C19 H19A 111.1 . . ?
C18 C19 H19B 111.1 . . ?
C20 C19 H19B 111.1 . . ?
H19A C19 H19B 109.0 . . ?
O3 C20 C19 113.3(11) . . ?
O3 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
O3 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S3 C1 C4 -177.1(5) . . . . ?
C3 S3 C1 S4 3.0(4) . . . . ?
C2 S4 C1 C4 176.5(5) . . . . ?
C2 S4 C1 S3 -3.6(4) . . . . ?
C1 S4 C2 C3 3.3(7) . . . . ?
S4 C2 C3 S3 -1.8(9) . . . . ?
C1 S3 C3 C2 -0.8(6) . . . . ?
S3 C1 C4 S1 177.8(3) . . . . ?
S4 C1 C4 S1 -2.3(6) . . . . ?
S3 C1 C4 S2 -1.3(6) . . . . ?
S4 C1 C4 S2 178.6(3) . . . . ?
C5 S1 C4 C1 -179.7(4) . . . . ?
C5 S1 C4 S2 -0.5(3) . . . . ?
C6 S2 C4 C1 179.7(4) . . . . ?
C6 S2 C4 S1 0.5(3) . . . . ?
C4 S1 C5 C6 0.4(4) . . . . ?
C4 S1 C5 C7 -178.8(3) . . . . ?
C7 C5 C6 S2 178.9(3) . . . . ?
S1 C5 C6 S2 -0.2(5) . . . . ?
C4 S2 C6 C5 -0.2(4) . . . . ?
C6 C5 C7 C10 177.6(5) . . . . ?
S1 C5 C7 C10 -3.3(6) . . . . ?
C6 C5 C7 C8 -2.5(7) . . . . ?
S1 C5 C7 C8 176.5(3) . . . . ?
C9 N2 C8 O2 174.1(4) . . . . ?
C9 N2 C8 C7 -4.8(6) . . . . ?
C10 C7 C8 O2 -173.7(4) . . . . ?
C5 C7 C8 O2 6.4(7) . . . . ?
C10 C7 C8 N2 5.1(6) . . . . ?
C5 C7 C8 N2 -174.8(3) . . . . ?
C8 N2 C9 O1 -178.8(4) . . . . ?
C8 N2 C9 N1 0.2(6) . . . . ?
C10 N1 C9 O1 -176.8(4) . . . . ?
C11 N1 C9 O1 9.2(6) . . . . ?
C10 N1 C9 N2 4.3(6) . . . . ?
C11 N1 C9 N2 -169.7(3) . . . . ?
C8 C7 C10 N1 -1.3(6) . . . . ?
C5 C7 C10 N1 178.6(4) . . . . ?
C9 N1 C10 C7 -3.8(6) . . . . ?
C11 N1 C10 C7 170.2(4) . . . . ?
C10 N1 C11 C12 119.5(4) . . . . ?
C9 N1 C11 C12 -66.3(5) . . . . ?
C10 N1 C11 C16 -58.4(5) . . . . ?
C9 N1 C11 C16 115.7(4) . . . . ?
C16 C11 C12 C13 -1.9(7) . . . . ?
N1 C11 C12 C13 -179.8(4) . . . . ?
C11 C12 C13 C14 1.5(7) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C12 C11 C16 C15 1.3(6) . . . . ?
N1 C11 C16 C15 179.2(4) . . . . ?
C14 C15 C16 C11 -0.2(6) . . . . ?
C20 O3 C17 C18 -14.0(16) . . . . ?
O3 C17 C18 C19 16.6(16) . . . . ?
C17 C18 C19 C20 -10.7(14) . . . . ?
C17 O3 C20 C19 5.4(15) . . . . ?
C18 C19 C20 O3 4.1(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.896
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.096

_iucr_refine_instructions_details 
;

TITL eigo
CELL 0.71075 18.86330 5.72210 21.50960 90.000 116.959 90.000
ZERR 4 0.00810 0.00290 0.00860 0.000 0.031 0.000
LATT 1
SYMM -X, .50+Y, .50-Z
SFAC C H O N S
UNIT 75.920000 63.840000 11 8 16
SHEL 99999.000000 0.000000
L.S. 30
FMAP 2
PLAN -20
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -73.0
ACTA
SIZE 0.650 0.200 0.060
DFIX 1.4300 0.0200 O3 C17
DFIX 1.4300 0.0200 O3 C20
DFIX 1.5400 0.0200 C17 C18
DFIX 1.5400 0.0200 C18 C19
DFIX 1.5400 0.0200 C19 C20
WGHT 0.136400
FVAR 0.85688 0.73972 0.11674
S1 5 0.256117 0.955178 0.076463 11.00000 0.03893 0.04387 =
0.03791 -0.00804 0.02168 -0.01189
S2 5 0.252351 1.097361 0.206214 11.00000 0.05090 0.05547 =
0.04439 -0.01686 0.02626 -0.00672
S3 5 0.377968 1.508686 0.229643 11.00000 0.04261 0.05270 =
0.07704 -0.02604 0.01150 -0.00053
S4 5 0.388301 1.362555 0.102067 11.00000 0.06719 0.06789 =
0.08274 -0.00640 0.04131 -0.02747
O1 3 0.033049 0.043833 -0.065560 11.00000 0.04648 0.02962 =
0.04385 -0.00055 0.02781 -0.00777
O2 3 0.082563 0.485265 0.124306 11.00000 0.05506 0.04484 =
0.04007 0.00162 0.03435 -0.00226
O3 3 0.287206 0.743854 0.436480 21.00000 31.00000
N1 4 0.110433 0.371506 -0.047482 11.00000 0.03281 0.02904 =
0.02776 0.00278 0.01738 -0.00224
N2 4 0.063212 0.267080 0.030826 11.00000 0.03660 0.02891 =
0.03483 0.00966 0.02199 -0.00095
AFIX 43
H2 2 0.035912 0.169524 0.043314 11.00000 -1.20000
AFIX 0
C1 1 0.345105 1.314212 0.158605 11.00000 0.03223 0.03979 =
0.05195 -0.00573 0.01171 0.00128
C2 1 0.441380 1.613618 0.148607 11.00000 0.05154 0.05947 =
0.11060 0.00886 0.01748 -0.02526
AFIX 43
H2A 2 0.472348 1.703014 0.132650 11.00000 -1.20000
AFIX 0
C3 1 0.436723 1.671271 0.204705 11.00000 0.05008 0.04272 =
0.09641 -0.00587 0.00505 -0.01044
AFIX 43
H3 2 0.465463 1.801796 0.231634 11.00000 -1.20000
AFIX 0
C4 1 0.292613 1.145429 0.148114 11.00000 0.02935 0.03576 =
0.03811 -0.00490 0.01205 0.00260
C5 1 0.192652 0.795838 0.101024 11.00000 0.03053 0.03262 =
0.03276 0.00525 0.01630 0.00409
C6 1 0.192546 0.866308 0.160452 11.00000 0.04278 0.04481 =
0.03943 -0.00129 0.02368 -0.00083
AFIX 43
H6 2 0.159882 0.789848 0.177215 11.00000 -1.20000
AFIX 0
C7 1 0.147396 0.602683 0.055995 11.00000 0.02572 0.02942 =
0.03059 0.00324 0.01402 -0.00030
C8 1 0.097172 0.455163 0.075273 11.00000 0.03234 0.02847 =
0.03471 0.00828 0.01770 0.00606
C9 1 0.066499 0.212656 -0.030158 11.00000 0.03153 0.02728 =
0.03510 0.00687 0.01830 0.00184
C10 1 0.150449 0.553509 -0.004446 11.00000 0.03091 0.02625 =
0.03179 0.00239 0.01591 -0.00294
AFIX 43
H10 2 0.182132 0.650790 -0.017687 11.00000 -1.20000
AFIX 0
C11 1 0.107460 0.356723 -0.116325 11.00000 0.02868 0.03074 =
0.02826 0.00088 0.01671 -0.00416
C12 1 0.138758 0.166048 -0.134136 11.00000 0.04267 0.02984 =
0.04264 0.00245 0.02530 0.00140
AFIX 43
H12 2 0.162424 0.041902 -0.101973 11.00000 -1.20000
AFIX 0
C13 1 0.135091 0.158507 -0.200125 11.00000 0.05158 0.03801 =
0.05295 -0.01296 0.03473 -0.00774
AFIX 43
H13 2 0.155233 0.026438 -0.213760 11.00000 -1.20000
AFIX 0
C14 1 0.102306 0.342125 -0.245891 11.00000 0.04580 0.04591 =
0.03621 -0.00810 0.02657 -0.01322
AFIX 43
H14 2 0.100424 0.336237 -0.290753 11.00000 -1.20000
AFIX 0
C15 1 0.072095 0.535102 -0.226941 11.00000 0.03845 0.03825 =
0.03102 0.00259 0.01885 -0.00267
AFIX 43
H15 2 0.049663 0.661387 -0.258544 11.00000 -1.20000
AFIX 0
C16 1 0.074941 0.542137 -0.161030 11.00000 0.03535 0.03133 =
0.03155 0.00038 0.01917 -0.00018
AFIX 43
H16 2 0.054663 0.673405 -0.147184 11.00000 -1.20000
AFIX 0
C17 1 0.300762 0.894702 0.395052 21.00000 31.00000
AFIX 23
H17A 2 0.292392 1.054805 0.407897 21.00000 -1.20000
H17B 2 0.259922 0.867242 0.346474 21.00000 -1.20000
AFIX 0
C18 1 0.379761 0.888112 0.395956 21.00000 31.00000
AFIX 23
H18A 2 0.414344 1.017214 0.424132 21.00000 -1.20000
H18B 2 0.375065 0.894287 0.348239 21.00000 -1.20000
AFIX 0
C19 1 0.409678 0.655303 0.429540 21.00000 31.00000
AFIX 23
H19A 2 0.463943 0.668586 0.468626 21.00000 -1.20000
H19B 2 0.410283 0.540633 0.395319 21.00000 -1.20000
AFIX 0
C20 1 0.350403 0.585658 0.455501 21.00000 31.00000
AFIX 23
H20A 2 0.328697 0.429494 0.436641 21.00000 -1.20000
H20B 2 0.378349 0.573153 0.506986 21.00000 -1.20000
HKLF 4

REM eigo
REM R1 = 0.0691 for 2597 Fo > 4sig(Fo) and 0.1107 for all 4269 data
REM 234 parameters refined using 5 restraints

END

WGHT 0.1456 0.0000
REM Highest difference peak 1.126, deepest hole -0.588, 1-sigma level 0.096
Q1 1 0.4579 1.1913 0.1209 11.00000 0.05 1.13
Q2 1 0.3651 0.5690 0.4010 11.00000 0.05 0.89
Q3 1 0.4488 0.8328 0.4449 11.00000 0.05 0.77
Q4 1 0.3038 0.7931 0.3697 11.00000 0.05 0.59
Q5 1 0.3329 0.7245 0.3719 11.00000 0.05 0.56
Q6 1 0.3593 1.3589 0.0563 11.00000 0.05 0.37
Q7 1 0.3229 1.4658 0.0257 11.00000 0.05 0.37
Q8 1 0.3657 1.3458 0.1332 11.00000 0.05 0.36
Q9 1 0.2748 1.1053 0.1757 11.00000 0.05 0.32
Q10 1 0.1222 0.5407 0.0621 11.00000 0.05 0.29
Q11 1 0.3585 1.4575 0.2591 11.00000 0.05 0.28
Q12 1 0.1817 0.6966 0.0887 11.00000 0.05 0.26
Q13 1 0.0906 0.5305 -0.1808 11.00000 0.05 0.26
Q14 1 0.0995 0.4539 -0.2287 11.00000 0.05 0.25
Q15 1 0.1588 0.5652 0.0315 11.00000 0.05 0.25
Q16 1 0.2271 0.8664 0.0926 11.00000 0.05 0.25
Q17 1 0.1629 0.1911 -0.1649 11.00000 0.05 0.22
Q18 1 0.0812 0.5038 0.0966 11.00000 0.05 0.22
Q19 1 0.1096 0.3619 -0.0824 11.00000 0.05 0.22
Q20 1 0.0886 0.3163 -0.0387 11.00000 0.05 0.22
;

#===END

data_TTF-PhU_Py
_database_code_depnum_ccdc_archive 'CCDC 826939'
#TrackingRef '- CIF.cif'

_audit_creation_method           SHELXL-97
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;

#Assistant Professor

#Department of Chemistry, Graduate School of Science, Osaka University
#Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan

_chemical_name_systematic        
;
TTFPhU-pyridine
;
_chemical_name_common            TTFPhU-pyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 N2 O2 S4, C5 H5 N1'
_chemical_formula_sum            'C21 H15 N3 O2 S4'
_chemical_formula_weight         469.60

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'
O O 0.0106 0.0060 '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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   35.208(2)
_cell_length_b                   5.6195(3)
_cell_length_c                   25.610(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.721(2)
_cell_angle_gamma                90.00
_cell_volume                     4061.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    11932
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.45

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8272
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\^A\/Ya
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \^A\/Yw
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17165
_diffrn_reflns_av_R_equivalents  0.1395
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4638
_reflns_number_gt                2296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID AUTO'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'

_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/[\^A\/Ys^2^(Fo^2^)+(0.0510P)^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         4638
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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 0.07245(4) 0.3411(2) 0.32160(6) 0.0428(3) Uani 1 1 d . . .
S2 S 0.14115(4) 0.23284(19) 0.29489(5) 0.0356(3) Uani 1 1 d . . .
S3 S 0.02942(4) 0.7723(2) 0.21412(6) 0.0439(3) Uani 1 1 d . . .
S4 S 0.09806(4) 0.6511(2) 0.18732(6) 0.0468(3) Uani 1 1 d . . .
O1 O 0.27086(9) -0.6946(4) 0.45201(14) 0.0360(7) Uani 1 1 d . . .
O2 O 0.16263(10) -0.2773(5) 0.45686(15) 0.0429(7) Uani 1 1 d . . .
N1 N 0.21574(10) -0.4786(5) 0.45129(15) 0.0302(8) Uani 1 1 d . . .
H1 H 0.2185 -0.5791 0.4798 0.036 Uiso 1 1 calc R . .
N2 N 0.23944(10) -0.3590(5) 0.38869(15) 0.0280(7) Uani 1 1 d . . .
N3 N 0.06461(18) 0.0847(7) 0.5163(2) 0.0669(12) Uani 1 1 d . . .
C1 C 0.07603(13) 0.5870(7) 0.2318(2) 0.0341(10) Uani 1 1 d . . .
C2 C 0.03031(16) 0.9466(8) 0.1591(2) 0.0473(12) Uani 1 1 d . . .
H2 H 0.0091 1.0767 0.1379 0.057 Uiso 1 1 calc R . .
C3 C 0.06105(15) 0.8956(8) 0.1470(2) 0.0488(12) Uani 1 1 d . . .
H3 H 0.0629 0.9883 0.1175 0.059 Uiso 1 1 calc R . .
C4 C 0.09336(13) 0.4112(7) 0.2759(2) 0.0314(9) Uani 1 1 d . . .
C5 C 0.11131(14) 0.1071(7) 0.3637(2) 0.0387(10) Uani 1 1 d . . .
H5 H 0.1101 0.0182 0.3942 0.046 Uiso 1 1 calc R . .
C6 C 0.14293(13) 0.0524(7) 0.35304(19) 0.0297(9) Uani 1 1 d . . .
C7 C 0.17779(13) -0.1381(7) 0.38217(19) 0.0299(9) Uani 1 1 d . . .
C8 C 0.20653(13) -0.1787(6) 0.36462(19) 0.0292(9) Uani 1 1 d . . .
H8 H 0.2038 -0.0750 0.3333 0.035 Uiso 1 1 calc R . .
C9 C 0.18338(14) -0.2965(7) 0.43218(19) 0.0321(10) Uani 1 1 d . . .
C10 C 0.24406(14) -0.5251(7) 0.43218(19) 0.0312(9) Uani 1 1 d . . .
C11 C 0.26957(13) -0.3704(6) 0.36746(19) 0.0273(9) Uani 1 1 d . . .
C12 C 0.29956(13) -0.1819(7) 0.3825(2) 0.0342(10) Uani 1 1 d . . .
H12 H 0.3016 -0.0531 0.4081 0.041 Uiso 1 1 calc R . .
C13 C 0.32684(14) -0.1838(7) 0.3595(2) 0.0402(11) Uani 1 1 d . . .
H13 H 0.3476 -0.0550 0.3693 0.048 Uiso 1 1 calc R . .
C14 C 0.32367(15) -0.3718(8) 0.3228(2) 0.0435(11) Uani 1 1 d . . .
H14 H 0.3422 -0.3725 0.3070 0.052 Uiso 1 1 calc R . .
C15 C 0.29357(15) -0.5601(8) 0.3086(2) 0.0439(11) Uani 1 1 d . . .
H15 H 0.2918 -0.6902 0.2835 0.053 Uiso 1 1 calc R . .
C16 C 0.26601(14) -0.5604(7) 0.3306(2) 0.0358(10) Uani 1 1 d . . .
H16 H 0.2451 -0.6887 0.3206 0.043 Uiso 1 1 calc R . .
C18 C 0.10112(19) 0.1121(11) 0.5139(3) 0.0679(16) Uani 1 1 d . . .
H18 H 0.1244 -0.0101 0.5316 0.082 Uiso 1 1 calc R . .
C19 C 0.10691(18) 0.3048(11) 0.4874(3) 0.0631(15) Uani 1 1 d . . .
H19 H 0.1340 0.3197 0.4879 0.076 Uiso 1 1 calc R . .
C20 C 0.0734(2) 0.4734(10) 0.4605(3) 0.0730(17) Uani 1 1 d . . .
H20 H 0.0760 0.6090 0.4407 0.088 Uiso 1 1 calc R . .
C21 C 0.0358(2) 0.4488(10) 0.4619(3) 0.0677(15) Uani 1 1 d . . .
H21 H 0.0120 0.5681 0.4438 0.081 Uiso 1 1 calc R . .
C22 C 0.03257(17) 0.2529(9) 0.4893(3) 0.0543(13) Uani 1 1 d . . .
H22 H 0.0056 0.2360 0.4890 0.065 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 0.0471(7) 0.0493(6) 0.0465(8) 0.0084(6) 0.0357(6) 0.0112(6)
S2 0.0413(6) 0.0408(6) 0.0340(7) 0.0074(5) 0.0274(6) 0.0088(5)
S3 0.0421(6) 0.0502(7) 0.0430(7) 0.0082(6) 0.0274(6) 0.0114(6)
S4 0.0542(7) 0.0525(7) 0.0472(8) 0.0090(6) 0.0376(7) 0.0096(6)
O1 0.0448(16) 0.0319(15) 0.0397(18) 0.0112(13) 0.0298(15) 0.0107(14)
O2 0.0558(18) 0.0465(17) 0.050(2) 0.0096(15) 0.0440(17) 0.0068(15)
N1 0.0377(19) 0.0296(17) 0.029(2) 0.0066(15) 0.0229(17) 0.0004(16)
N2 0.0323(18) 0.0300(17) 0.0249(19) 0.0031(15) 0.0188(16) -0.0011(15)
N3 0.105(4) 0.051(3) 0.068(3) 0.003(2) 0.065(3) -0.001(3)
C1 0.032(2) 0.034(2) 0.034(3) -0.003(2) 0.019(2) 0.0030(19)
C2 0.048(3) 0.048(3) 0.036(3) 0.013(2) 0.020(2) 0.009(2)
C3 0.054(3) 0.051(3) 0.036(3) 0.008(2) 0.025(3) -0.003(2)
C4 0.031(2) 0.036(2) 0.031(2) -0.0048(19) 0.021(2) 0.0001(19)
C5 0.046(3) 0.041(2) 0.040(3) 0.005(2) 0.031(2) 0.002(2)
C6 0.033(2) 0.034(2) 0.027(2) -0.0018(18) 0.020(2) -0.0004(19)
C7 0.032(2) 0.036(2) 0.022(2) 0.0006(18) 0.0161(19) -0.0039(19)
C8 0.036(2) 0.028(2) 0.029(2) 0.0043(17) 0.022(2) -0.0025(19)
C9 0.037(2) 0.031(2) 0.028(2) -0.0033(18) 0.019(2) -0.0064(19)
C10 0.035(2) 0.035(2) 0.028(2) -0.0059(19) 0.021(2) -0.005(2)
C11 0.029(2) 0.031(2) 0.027(2) 0.0102(18) 0.0199(19) 0.0070(18)
C12 0.041(2) 0.033(2) 0.036(3) 0.0031(19) 0.027(2) 0.004(2)
C13 0.044(2) 0.041(2) 0.047(3) 0.009(2) 0.033(2) 0.000(2)
C14 0.048(3) 0.056(3) 0.041(3) 0.016(2) 0.035(2) 0.018(2)
C15 0.060(3) 0.043(2) 0.039(3) 0.005(2) 0.035(3) 0.012(2)
C16 0.045(2) 0.036(2) 0.037(3) 0.003(2) 0.030(2) 0.000(2)
C18 0.066(4) 0.087(4) 0.046(4) 0.010(3) 0.031(3) 0.033(3)
C19 0.052(3) 0.099(5) 0.047(3) -0.019(3) 0.035(3) -0.017(3)
C20 0.127(5) 0.051(3) 0.068(4) -0.005(3) 0.074(4) -0.016(4)
C21 0.084(4) 0.055(3) 0.067(4) 0.005(3) 0.047(3) 0.026(3)
C22 0.053(3) 0.064(3) 0.063(4) -0.012(3) 0.044(3) -0.004(3)

_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 1.732(4) . ?
S1 C4 1.760(4) . ?
S2 C4 1.759(4) . ?
S2 C6 1.771(4) . ?
S3 C2 1.733(5) . ?
S3 C1 1.758(4) . ?
S4 C3 1.745(5) . ?
S4 C1 1.757(4) . ?
O1 C10 1.217(4) . ?
O2 C9 1.223(5) . ?
N1 C10 1.373(5) . ?
N1 C9 1.385(5) . ?
N1 H1 0.8800 . ?
N2 C8 1.377(4) . ?
N2 C10 1.387(5) . ?
N2 C11 1.454(4) . ?
N3 C22 1.308(6) . ?
N3 C18 1.333(7) . ?
C1 C4 1.341(5) . ?
C2 C3 1.323(6) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.330(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.454(5) . ?
C7 C8 1.350(5) . ?
C7 C9 1.473(5) . ?
C8 H8 0.9500 . ?
C11 C12 1.378(5) . ?
C11 C16 1.380(5) . ?
C12 C13 1.395(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.356(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.339(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.352(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.346(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 C4 95.4(2) . . ?
C4 S2 C6 96.08(18) . . ?
C2 S3 C1 94.4(2) . . ?
C3 S4 C1 94.7(2) . . ?
C10 N1 C9 129.3(3) . . ?
C10 N1 H1 115.3 . . ?
C9 N1 H1 115.3 . . ?
C8 N2 C10 121.2(3) . . ?
C8 N2 C11 118.2(3) . . ?
C10 N2 C11 120.6(3) . . ?
C22 N3 C18 116.3(5) . . ?
C4 C1 S4 122.8(3) . . ?
C4 C1 S3 122.6(3) . . ?
S4 C1 S3 114.7(2) . . ?
C3 C2 S3 118.9(4) . . ?
C3 C2 H2 120.6 . . ?
S3 C2 H2 120.6 . . ?
C2 C3 S4 117.3(4) . . ?
C2 C3 H3 121.4 . . ?
S4 C3 H3 121.4 . . ?
C1 C4 S2 122.1(3) . . ?
C1 C4 S1 124.3(3) . . ?
S2 C4 S1 113.6(2) . . ?
C6 C5 S1 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
S1 C5 H5 120.2 . . ?
C5 C6 C7 128.2(4) . . ?
C5 C6 S2 115.2(3) . . ?
C7 C6 S2 116.6(3) . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 C9 116.8(4) . . ?
C6 C7 C9 121.6(3) . . ?
C7 C8 N2 125.0(4) . . ?
C7 C8 H8 117.5 . . ?
N2 C8 H8 117.5 . . ?
O2 C9 N1 120.1(4) . . ?
O2 C9 C7 125.8(4) . . ?
N1 C9 C7 114.1(3) . . ?
O1 C10 N1 123.2(4) . . ?
O1 C10 N2 123.4(3) . . ?
N1 C10 N2 113.4(3) . . ?
C12 C11 C16 121.8(3) . . ?
C12 C11 N2 118.0(3) . . ?
C16 C11 N2 120.1(3) . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 118.6(4) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N3 C18 C19 123.6(5) . . ?
N3 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
C20 C19 C18 118.2(5) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C21 119.3(5) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 119.1(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N3 C22 C21 123.4(5) . . ?
N3 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S4 C1 C4 -177.3(3) . . . . ?
C3 S4 C1 S3 2.6(3) . . . . ?
C2 S3 C1 C4 177.7(3) . . . . ?
C2 S3 C1 S4 -2.3(3) . . . . ?
C1 S3 C2 C3 0.9(4) . . . . ?
S3 C2 C3 S4 0.8(6) . . . . ?
C1 S4 C3 C2 -2.1(4) . . . . ?
S4 C1 C4 S2 1.8(5) . . . . ?
S3 C1 C4 S2 -178.1(2) . . . . ?
S4 C1 C4 S1 179.9(2) . . . . ?
S3 C1 C4 S1 0.0(5) . . . . ?
C6 S2 C4 C1 -179.8(3) . . . . ?
C6 S2 C4 S1 1.9(2) . . . . ?
C5 S1 C4 C1 179.8(3) . . . . ?
C5 S1 C4 S2 -2.0(3) . . . . ?
C4 S1 C5 C6 1.2(4) . . . . ?
S1 C5 C6 C7 -178.8(3) . . . . ?
S1 C5 C6 S2 -0.1(5) . . . . ?
C4 S2 C6 C5 -1.2(4) . . . . ?
C4 S2 C6 C7 177.8(3) . . . . ?
C5 C6 C7 C8 177.2(4) . . . . ?
S2 C6 C7 C8 -1.5(5) . . . . ?
C5 C6 C7 C9 -2.6(6) . . . . ?
S2 C6 C7 C9 178.6(3) . . . . ?
C6 C7 C8 N2 -178.2(3) . . . . ?
C9 C7 C8 N2 1.7(6) . . . . ?
C10 N2 C8 C7 3.2(6) . . . . ?
C11 N2 C8 C7 -176.6(4) . . . . ?
C10 N1 C9 O2 -176.7(4) . . . . ?
C10 N1 C9 C7 2.8(5) . . . . ?
C8 C7 C9 O2 175.2(4) . . . . ?
C6 C7 C9 O2 -4.9(6) . . . . ?
C8 C7 C9 N1 -4.3(5) . . . . ?
C6 C7 C9 N1 175.6(3) . . . . ?
C9 N1 C10 O1 -178.9(4) . . . . ?
C9 N1 C10 N2 1.7(5) . . . . ?
C8 N2 C10 O1 175.9(3) . . . . ?
C11 N2 C10 O1 -4.3(5) . . . . ?
C8 N2 C10 N1 -4.7(5) . . . . ?
C11 N2 C10 N1 175.1(3) . . . . ?
C8 N2 C11 C12 62.2(5) . . . . ?
C10 N2 C11 C12 -117.5(4) . . . . ?
C8 N2 C11 C16 -114.7(4) . . . . ?
C10 N2 C11 C16 65.6(5) . . . . ?
C16 C11 C12 C13 0.3(6) . . . . ?
N2 C11 C12 C13 -176.6(3) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
N2 C11 C16 C15 176.9(3) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C22 N3 C18 C19 2.3(8) . . . . ?
N3 C18 C19 C20 -2.1(8) . . . . ?
C18 C19 C20 C21 1.4(8) . . . . ?
C19 C20 C21 C22 -1.2(9) . . . . ?
C18 N3 C22 C21 -2.0(8) . . . . ?
C20 C21 C22 N3 1.5(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.070

#===END