# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Yoshitane Imai'
_publ_contact_author_email       Y-IMAI@APCH.KINDAI.AC.JP

_publ_section_title              
;
Conformational and color polymorphism of achiral
2-methyl-3-(2-naphthalenylthio)-1,4-naphthalenedione
;
loop_
_publ_author_name
'Yoshitane Imai'
'Takunori Harada'
'Takafumi Kinuta'
'Reiko Kuroda'
'Yoshio Matsubara'
'Keiko Nagasaki'
;
Y.Sasaki
;
'Tomohiro Sato'
'Nobuo Tajima'

# Attachment 'N3IMAI89.CIF'

data_imai89_1
_database_code_depnum_ccdc_archive 'CCDC 702857'
#data_im7662b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O2 S'
_chemical_formula_weight         330.38

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'
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   Cc

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'

_cell_length_a                   22.763(3)
_cell_length_b                   4.9872(5)
_cell_length_c                   13.6097(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.969(2)
_cell_angle_gamma                90.00
_cell_volume                     1536.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2715
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.15

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8977
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6362
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.85
_reflns_number_total             3232
_reflns_number_gt                2712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAMRT'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
The whole molecule is disordered into two orientation. Because of this,
it was necessary to restrain all the bond distances and angles to assume
standard values. Also the planarity of the naphthyl ring was imposed for
all four of them.

;

_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)+(0.0644P)²+0.9320P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.358(208)
_refine_ls_number_reflns         3232
_refine_ls_number_parameters     200
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.077
_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
C1 C 0.3765(3) 0.0794(13) 0.0253(5) 0.013(2) Uiso 0.50 1 d PD A 1
C2 C 0.4072(2) -0.1182(11) -0.0332(4) 0.0153(16) Uiso 0.50 1 d PD A 1
C3 C 0.3935(3) -0.1463(12) -0.1306(4) 0.0175(17) Uiso 0.50 1 d PD A 1
C4 C 0.3460(3) 0.0130(13) -0.1855(4) 0.0176(16) Uiso 0.50 1 d PD A 1
C5 C 0.2685(3) 0.3733(16) -0.1768(5) 0.0216(18) Uiso 0.50 1 d PD A 1
H5 H 0.2561 0.3509 -0.2451 0.026 Uiso 0.50 1 calc PR A 1
C6 C 0.2416(4) 0.5654(18) -0.1231(6) 0.024(2) Uiso 0.50 1 d PD A 1
H6 H 0.2114 0.6740 -0.1559 0.029 Uiso 0.50 1 calc PR A 1
C7 C 0.2574(4) 0.604(2) -0.0235(6) 0.035(3) Uiso 0.50 1 d PD A 1
H7 H 0.2387 0.7369 0.0123 0.042 Uiso 0.50 1 calc PR A 1
C8 C 0.3015(5) 0.442(2) 0.0227(8) 0.040(4) Uiso 0.50 1 d PD A 1
H8 H 0.3129 0.4647 0.0913 0.048 Uiso 0.50 1 calc PR A 1
C9 C 0.3300(4) 0.2441(19) -0.0295(6) 0.022(3) Uiso 0.50 1 d PD A 1
C10 C 0.3137(3) 0.2125(13) -0.1318(4) 0.0164(17) Uiso 0.50 1 d PD A 1
O1 O 0.3869(2) 0.0871(13) 0.1147(4) 0.0276(13) Uiso 0.50 1 d PD A 1
S2 S 0.45791(8) -0.3314(5) 0.03409(15) 0.0223(2) Uani 0.50 1 d PD A 1
C3M C 0.4228(3) -0.3326(13) -0.1979(5) 0.0180(17) Uiso 0.50 1 d PD A 1
H3M1 H 0.4635 -0.3677 -0.1698 0.027 Uiso 0.50 1 calc PR A 1
H3M2 H 0.4232 -0.2491 -0.2630 0.027 Uiso 0.50 1 calc PR A 1
H3M3 H 0.4009 -0.5018 -0.2046 0.027 Uiso 0.50 1 calc PR A 1
O4 O 0.3307(3) -0.0100(11) -0.2724(4) 0.0309(14) Uiso 0.50 1 d PD A 1
C11 C 0.5366(3) 0.0833(15) 0.0159(6) 0.025(2) Uiso 0.50 1 d PD A 1
H11 H 0.5224 0.0877 -0.0522 0.029 Uiso 0.50 1 calc PR A 1
C12 C 0.5133(2) -0.0962(11) 0.0779(5) 0.0154(17) Uiso 0.50 1 d PD A 1
C13 C 0.5323(3) -0.0876(17) 0.1803(5) 0.0205(17) Uiso 0.50 1 d PD A 1
H13 H 0.5132 -0.1951 0.2250 0.025 Uiso 0.50 1 calc PR A 1
C14 C 0.5782(3) 0.0760(15) 0.2145(5) 0.024(2) Uiso 0.50 1 d PD A 1
H14 H 0.5937 0.0626 0.2819 0.028 Uiso 0.50 1 calc PR A 1
C15 C 0.6488(4) 0.4464(18) 0.1844(6) 0.028(2) Uiso 0.50 1 d PD A 1
H15 H 0.6655 0.4542 0.2512 0.034 Uiso 0.50 1 calc PR A 1
C16 C 0.6683(4) 0.6149(19) 0.1135(6) 0.027(2) Uiso 0.50 1 d PD A 1
H16 H 0.6985 0.7406 0.1338 0.032 Uiso 0.50 1 calc PR A 1
C17 C 0.6458(4) 0.6102(17) 0.0128(6) 0.026(2) Uiso 0.50 1 d PD A 1
H17 H 0.6612 0.7274 -0.0331 0.031 Uiso 0.50 1 calc PR A 1
C18 C 0.6014(4) 0.4348(16) -0.0175(6) 0.019(3) Uiso 0.50 1 d PD A 1
H18 H 0.5845 0.4294 -0.0843 0.022 Uiso 0.50 1 calc PR A 1
C19 C 0.5819(3) 0.2625(14) 0.0542(5) 0.016(2) Uiso 0.50 1 d PD A 1
C20 C 0.6034(3) 0.2632(14) 0.1539(4) 0.0125(16) Uiso 0.50 1 d PD A 1
C21 C 0.5305(3) 0.0716(13) -0.0078(5) 0.016(2) Uiso 0.50 1 d PD B 2
C22 C 0.5012(2) -0.1236(12) 0.0526(5) 0.0214(19) Uiso 0.50 1 d PD B 2
C23 C 0.5151(3) -0.1447(13) 0.1515(4) 0.0184(17) Uiso 0.50 1 d PD B 2
C24 C 0.5616(3) 0.0297(15) 0.2016(5) 0.0194(18) Uiso 0.50 1 d PD B 2
C25 C 0.6368(4) 0.3854(18) 0.1882(6) 0.026(2) Uiso 0.50 1 d PD B 2
H25 H 0.6463 0.3621 0.2573 0.032 Uiso 0.50 1 calc PR B 2
C26 C 0.6675(4) 0.572(2) 0.1393(7) 0.031(2) Uiso 0.50 1 d PD B 2
H26 H 0.6991 0.6714 0.1727 0.037 Uiso 0.50 1 calc PR B 2
C27 C 0.6507(3) 0.6103(16) 0.0403(6) 0.019(2) Uiso 0.50 1 d PD B 2
H27 H 0.6692 0.7448 0.0049 0.022 Uiso 0.50 1 calc PR B 2
C28 C 0.6072(4) 0.4542(18) -0.0071(7) 0.022(3) Uiso 0.50 1 d PD B 2
H28 H 0.5974 0.4843 -0.0758 0.026 Uiso 0.50 1 calc PR B 2
C29 C 0.5754(3) 0.2496(15) 0.0381(5) 0.018(2) Uiso 0.50 1 d PD B 2
C30 C 0.5921(3) 0.2297(14) 0.1392(5) 0.0170(18) Uiso 0.50 1 d PD B 2
O21 O 0.5159(2) 0.0969(12) -0.0964(4) 0.0240(12) Uiso 0.50 1 d PD B 2
S22 S 0.44791(8) -0.3312(5) -0.01341(15) 0.0223(2) Uani 0.50 1 d PD B 2
C23M C 0.4840(4) -0.3354(17) 0.2139(6) 0.035(2) Uiso 0.50 1 d PD B 2
H23A H 0.4594 -0.4581 0.1711 0.053 Uiso 0.50 1 calc PR B 2
H23B H 0.4591 -0.2341 0.2552 0.053 Uiso 0.50 1 calc PR B 2
H23C H 0.5133 -0.4386 0.2562 0.053 Uiso 0.50 1 calc PR B 2
O24 O 0.5737(3) 0.0166(11) 0.2914(4) 0.0327(15) Uiso 0.50 1 d PD B 2
C31 C 0.3705(4) 0.0822(17) 0.0054(7) 0.021(3) Uiso 0.50 1 d PD B 2
H31 H 0.3835 0.0690 0.0739 0.025 Uiso 0.50 1 calc PR B 2
C32 C 0.3961(3) -0.0875(13) -0.0607(5) 0.0173(17) Uiso 0.50 1 d PD B 2
C33 C 0.3744(3) -0.0891(15) -0.1596(5) 0.0157(15) Uiso 0.50 1 d PD B 2
H33 H 0.3896 -0.2127 -0.2036 0.019 Uiso 0.50 1 calc PR B 2
C34 C 0.3310(3) 0.0879(14) -0.1938(5) 0.0132(14) Uiso 0.50 1 d PD B 2
H34 H 0.3175 0.0930 -0.2622 0.016 Uiso 0.50 1 calc PR B 2
C35 C 0.2615(3) 0.4493(15) -0.1625(5) 0.0125(14) Uiso 0.50 1 d PD B 2
H35 H 0.2478 0.4507 -0.2308 0.015 Uiso 0.50 1 calc PR B 2
C36 C 0.2384(3) 0.6238(16) -0.1012(5) 0.0163(17) Uiso 0.50 1 d PD B 2
H36 H 0.2084 0.7461 -0.1258 0.020 Uiso 0.50 1 calc PR B 2
C37 C 0.2597(3) 0.6214(15) 0.0011(6) 0.0130(17) Uiso 0.50 1 d PD B 2
H37 H 0.2434 0.7435 0.0446 0.016 Uiso 0.50 1 calc PR B 2
C38 C 0.3027(3) 0.4485(15) 0.0380(6) 0.0084(19) Uiso 0.50 1 d PD B 2
H38 H 0.3161 0.4497 0.1065 0.010 Uiso 0.50 1 calc PR B 2
C39 C 0.3267(4) 0.2703(17) -0.0254(6) 0.010(2) Uiso 0.50 1 d PD B 2
C40 C 0.3058(4) 0.2650(17) -0.1270(6) 0.022(2) Uiso 0.50 1 d PD B 2


_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
C1 O1 1.216(6) . ?
C1 C9 1.480(7) . ?
C1 C2 1.486(6) . ?
C2 C3 1.337(6) . ?
C2 S2 1.755(6) . ?
C3 C4 1.479(6) . ?
C3 C3M 1.509(6) . ?
C4 O4 1.203(6) . ?
C4 C10 1.476(6) . ?
C5 C6 1.386(7) . ?
C5 C10 1.393(6) . ?
C6 C7 1.379(7) . ?
C7 C8 1.387(8) . ?
C8 C9 1.411(7) . ?
C9 C10 1.412(7) . ?
S2 C12 1.779(6) . ?
C11 C12 1.373(6) . ?
C11 C19 1.422(7) . ?
C12 C13 1.415(6) . ?
C13 C14 1.369(7) . ?
C14 C20 1.407(6) . ?
C15 C16 1.386(6) . ?
C15 C20 1.410(7) . ?
C16 C17 1.412(7) . ?
C17 C18 1.367(7) . ?
C18 C19 1.407(7) . ?
C19 C20 1.394(6) . ?
C21 O21 1.223(7) . ?
C21 C29 1.446(8) . ?
C21 C22 1.477(7) . ?
C22 C23 1.354(8) . ?
C22 S22 1.767(7) . ?
C23 C24 1.481(8) . ?
C23 C23M 1.500(8) . ?
C24 O24 1.226(7) . ?
C24 C30 1.524(8) . ?
C25 C26 1.378(9) . ?
C25 C30 1.393(8) . ?
C26 C27 1.375(9) . ?
C27 C28 1.366(9) . ?
C28 C29 1.427(10) . ?
C29 C30 1.393(9) . ?
S22 C32 1.768(6) . ?
C31 C39 1.402(9) . ?
C31 C32 1.404(8) . ?
C32 C33 1.385(7) . ?
C33 C34 1.370(7) . ?
C34 C40 1.429(8) . ?
C35 C36 1.351(7) . ?
C35 C40 1.412(8) . ?
C36 C37 1.426(8) . ?
C37 C38 1.360(8) . ?
C38 C39 1.390(10) . ?
C39 C40 1.415(9) . ?

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
O1 C1 C9 122.8(6) . . ?
O1 C1 C2 120.2(6) . . ?
C9 C1 C2 116.8(6) . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 S2 121.8(4) . . ?
C1 C2 S2 116.3(4) . . ?
C2 C3 C4 121.9(5) . . ?
C2 C3 C3M 126.4(5) . . ?
C4 C3 C3M 111.7(5) . . ?
O4 C4 C10 116.3(6) . . ?
O4 C4 C3 124.5(6) . . ?
C10 C4 C3 119.2(5) . . ?
C6 C5 C10 120.8(6) . . ?
C7 C6 C5 122.1(7) . . ?
C6 C7 C8 117.8(8) . . ?
C7 C8 C9 121.9(9) . . ?
C8 C9 C10 119.1(7) . . ?
C8 C9 C1 118.5(7) . . ?
C10 C9 C1 122.4(6) . . ?
C5 C10 C9 118.4(6) . . ?
C5 C10 C4 123.6(6) . . ?
C9 C10 C4 118.0(6) . . ?
C2 S2 C12 100.4(3) . . ?
C12 C11 C19 119.7(7) . . ?
C11 C12 C13 119.2(6) . . ?
C11 C12 S2 121.9(5) . . ?
C13 C12 S2 118.8(5) . . ?
C14 C13 C12 119.8(6) . . ?
C13 C14 C20 122.6(7) . . ?
C16 C15 C20 117.8(7) . . ?
C15 C16 C17 123.7(7) . . ?
C18 C17 C16 119.1(8) . . ?
C17 C18 C19 117.3(7) . . ?
C20 C19 C18 124.7(6) . . ?
C20 C19 C11 121.8(6) . . ?
C18 C19 C11 113.6(6) . . ?
C19 C20 C14 116.5(6) . . ?
C19 C20 C15 117.4(6) . . ?
C14 C20 C15 126.1(6) . . ?
O21 C21 C29 118.0(6) . . ?
O21 C21 C22 121.6(6) . . ?
C29 C21 C22 120.3(6) . . ?
C23 C22 C21 122.1(6) . . ?
C23 C22 S22 122.5(5) . . ?
C21 C22 S22 115.4(5) . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 C23M 122.5(6) . . ?
C24 C23 C23M 117.9(6) . . ?
O24 C24 C23 120.3(6) . . ?
O24 C24 C30 121.5(7) . . ?
C23 C24 C30 118.2(6) . . ?
C26 C25 C30 121.8(8) . . ?
C27 C26 C25 117.6(8) . . ?
C28 C27 C26 119.9(8) . . ?
C27 C28 C29 125.4(8) . . ?
C30 C29 C28 112.2(7) . . ?
C30 C29 C21 119.4(6) . . ?
C28 C29 C21 128.4(7) . . ?
C29 C30 C25 123.0(7) . . ?
C29 C30 C24 120.3(6) . . ?
C25 C30 C24 116.8(6) . . ?
C32 S22 C22 100.3(3) . . ?
C39 C31 C32 122.8(8) . . ?
C33 C32 C31 119.8(6) . . ?
C33 C32 S22 120.5(5) . . ?
C31 C32 S22 119.1(5) . . ?
C34 C33 C32 119.9(6) . . ?
C33 C34 C40 120.3(6) . . ?
C36 C35 C40 121.3(6) . . ?
C35 C36 C37 118.9(6) . . ?
C38 C37 C36 121.6(7) . . ?
C37 C38 C39 119.4(8) . . ?
C38 C39 C31 123.8(7) . . ?
C38 C39 C40 120.3(7) . . ?
C31 C39 C40 115.8(8) . . ?
C35 C40 C39 118.5(6) . . ?
C35 C40 C34 120.2(6) . . ?
C39 C40 C34 121.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.85
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.052

#===END

data_imai89_2
_database_code_depnum_ccdc_archive 'CCDC 702858'
#data_im8788a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O2 S'
_chemical_formula_weight         330.38

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'
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   P2(1)

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

_cell_length_a                   8.0141(17)
_cell_length_b                   5.8339(12)
_cell_length_c                   16.979(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.228(3)
_cell_angle_gamma                90.00
_cell_volume                     787.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.88

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(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  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6936
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3513
_reflns_number_gt                3201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0504P)²+0.0617P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_number_reflns         3513
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002

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
C1 C 0.7771(3) 0.4840(4) 0.79674(12) 0.0217(4) Uani 1 1 d . . .
C2 C 0.6137(3) 0.3569(4) 0.78323(12) 0.0195(4) Uani 1 1 d . . .
C3 C 0.4786(3) 0.4174(4) 0.81792(12) 0.0213(5) Uani 1 1 d . . .
C4 C 0.4849(2) 0.6280(4) 0.86794(11) 0.0220(4) Uani 1 1 d . . .
C5 C 0.6585(3) 0.9346(4) 0.93907(13) 0.0261(5) Uani 1 1 d . . .
H5 H 0.5627 0.9810 0.9628 0.031 Uiso 1 1 calc R . .
C6 C 0.8082(3) 1.0530(4) 0.95561(13) 0.0299(5) Uani 1 1 d . . .
H6 H 0.8158 1.1796 0.9911 0.036 Uiso 1 1 calc R . .
C7 C 0.9475(3) 0.9859(4) 0.92019(13) 0.0295(5) Uani 1 1 d . . .
H7 H 1.0502 1.0681 0.9311 0.035 Uiso 1 1 calc R . .
C8 C 0.9379(3) 0.8010(4) 0.86928(13) 0.0251(5) Uani 1 1 d . . .
H8 H 1.0340 0.7566 0.8454 0.030 Uiso 1 1 calc R . .
C9 C 0.7890(3) 0.6795(4) 0.85268(12) 0.0209(4) Uani 1 1 d . . .
C10 C 0.6478(3) 0.7480(4) 0.88789(12) 0.0217(4) Uani 1 1 d . . .
C3M C 0.3161(3) 0.2883(4) 0.80960(14) 0.0280(5) Uani 1 1 d . . .
H3M1 H 0.3017 0.2064 0.7588 0.042 Uiso 1 1 calc R . .
H3M2 H 0.2228 0.3958 0.8114 0.042 Uiso 1 1 calc R . .
H3M3 H 0.3175 0.1779 0.8532 0.042 Uiso 1 1 calc R . .
O1 O 0.89780(19) 0.4252(3) 0.76490(9) 0.0303(4) Uani 1 1 d . . .
O4 O 0.35742(19) 0.7028(3) 0.89140(9) 0.0306(4) Uani 1 1 d . . .
S S 0.61082(6) 0.10246(8) 0.72678(3) 0.02238(13) Uani 1 1 d . . .
C11 C 0.7519(2) 0.0438(3) 0.59229(12) 0.0182(4) Uani 1 1 d . . .
H11 H 0.7919 -0.0963 0.6162 0.022 Uiso 1 1 calc R . .
C12 C 0.6667(2) 0.1954(4) 0.63427(11) 0.0178(4) Uani 1 1 d . . .
C13 C 0.6089(2) 0.4068(3) 0.60017(12) 0.0179(4) Uani 1 1 d . . .
H13 H 0.5492 0.5105 0.6295 0.021 Uiso 1 1 calc R . .
C14 C 0.6389(2) 0.4612(3) 0.52535(11) 0.0170(4) Uani 1 1 d . . .
H14 H 0.6019 0.6049 0.5033 0.020 Uiso 1 1 calc R . .
C15 C 0.7539(2) 0.3590(4) 0.40111(12) 0.0211(5) Uani 1 1 d . . .
H15 H 0.7163 0.5009 0.3778 0.025 Uiso 1 1 calc R . .
C16 C 0.8361(2) 0.2062(4) 0.35848(12) 0.0220(4) Uani 1 1 d . . .
H16 H 0.8551 0.2426 0.3058 0.026 Uiso 1 1 calc R . .
C17 C 0.8931(3) -0.0057(4) 0.39243(12) 0.0214(4) Uani 1 1 d . . .
H17 H 0.9508 -0.1105 0.3626 0.026 Uiso 1 1 calc R . .
C18 C 0.8653(2) -0.0597(3) 0.46780(12) 0.0190(4) Uani 1 1 d . . .
H18 H 0.9032 -0.2029 0.4899 0.023 Uiso 1 1 calc R . .
C19 C 0.7807(2) 0.0945(4) 0.51355(11) 0.0166(4) Uani 1 1 d . . .
C20 C 0.7244(2) 0.3075(3) 0.47948(12) 0.0166(4) Uani 1 1 d . . .


_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
C1 O1 1.216(2) . ?
C1 C9 1.479(3) . ?
C1 C2 1.497(3) . ?
C2 C3 1.343(3) . ?
C2 S 1.765(2) . ?
C3 C4 1.491(3) . ?
C3 C3M 1.496(3) . ?
C4 O4 1.223(2) . ?
C4 C10 1.482(3) . ?
C5 C6 1.382(3) . ?
C5 C10 1.389(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.403(3) . ?
S C12 1.772(2) . ?
C11 C12 1.371(3) . ?
C11 C19 1.416(3) . ?
C12 C13 1.416(3) . ?
C13 C14 1.360(3) . ?
C14 C20 1.419(3) . ?
C15 C16 1.369(3) . ?
C15 C20 1.413(3) . ?
C16 C17 1.415(3) . ?
C17 C18 1.363(3) . ?
C18 C19 1.416(3) . ?
C19 C20 1.420(3) . ?

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
O1 C1 C9 120.82(19) . . ?
O1 C1 C2 121.4(2) . . ?
C9 C1 C2 117.72(18) . . ?
C3 C2 C1 122.7(2) . . ?
C3 C2 S 120.19(17) . . ?
C1 C2 S 116.84(15) . . ?
C2 C3 C4 119.69(19) . . ?
C2 C3 C3M 124.5(2) . . ?
C4 C3 C3M 115.82(18) . . ?
O4 C4 C10 120.3(2) . . ?
O4 C4 C3 120.67(19) . . ?
C10 C4 C3 118.99(17) . . ?
C6 C5 C10 120.2(2) . . ?
C5 C6 C7 119.7(2) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C8 C9 120.4(2) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 C1 120.62(19) . . ?
C10 C9 C1 120.16(19) . . ?
C5 C10 C9 120.0(2) . . ?
C5 C10 C4 119.76(19) . . ?
C9 C10 C4 120.19(19) . . ?
C2 S C12 103.69(10) . . ?
C12 C11 C19 120.46(19) . . ?
C11 C12 C13 120.56(18) . . ?
C11 C12 S 117.50(16) . . ?
C13 C12 S 121.52(16) . . ?
C14 C13 C12 119.88(19) . . ?
C13 C14 C20 121.29(18) . . ?
C16 C15 C20 120.6(2) . . ?
C15 C16 C17 120.37(19) . . ?
C18 C17 C16 120.13(19) . . ?
C17 C18 C19 120.95(19) . . ?
C11 C19 C18 122.09(19) . . ?
C11 C19 C20 119.09(18) . . ?
C18 C19 C20 118.81(18) . . ?
C15 C20 C14 122.14(18) . . ?
C15 C20 C19 119.17(18) . . ?
C14 C20 C19 118.69(18) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052


