

data_1

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          ?

_chemical_formula_sum

 'C18 H10 S2'

_chemical_formula_weight          290.38

 

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'

 'S'  'S'   0.1246   0.1234

 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

 

_symmetry_cell_setting            Orthorhombic

_symmetry_space_group_name_H-M    P2(1)2(1)2(1)

 

loop_

 _symmetry_equiv_pos_as_xyz

 'x, y, z'

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

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

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

 

_cell_length_a                    3.9971(16)

_cell_length_b                    10.334(4)

_cell_length_c                    31.473(13)

_cell_angle_alpha                 90.00

_cell_angle_beta                  90.00

_cell_angle_gamma                 90.00

_cell_volume                      1300.1(9)

_cell_formula_units_Z             4

_cell_measurement_temperature     296(2)

_cell_measurement_reflns_used     3483

_cell_measurement_theta_min       2.59

_cell_measurement_theta_max       28.04

 

_exptl_crystal_description        Rod

_exptl_crystal_colour             Yellow

_exptl_crystal_size_max           0.29

_exptl_crystal_size_mid           0.15

_exptl_crystal_size_min           0.10

_exptl_crystal_density_meas       ?

_exptl_crystal_density_diffrn     1.484

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              600

_exptl_absorpt_coefficient_mu     0.393

_exptl_absorpt_correction_type    Multi-scan

_exptl_absorpt_correction_T_min   0.8946

_exptl_absorpt_correction_T_max   0.9618

_exptl_absorpt_process_details    SADABS

 

_exptl_special_details

;

 ?

;

 

_diffrn_ambient_temperature       296(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        'phi and omega scans'

_diffrn_detector_area_resol_mean  ?

_diffrn_standards_number          ?

_diffrn_standards_interval_count  ?

_diffrn_standards_interval_time   ?

_diffrn_standards_decay_%         ?

_diffrn_reflns_number             7988

_diffrn_reflns_av_R_equivalents   0.0242

_diffrn_reflns_av_sigmaI/netI     0.0305

_diffrn_reflns_limit_h_min        -5

_diffrn_reflns_limit_h_max        5

_diffrn_reflns_limit_k_min        -13

_diffrn_reflns_limit_k_max        10

_diffrn_reflns_limit_l_min        -37

_diffrn_reflns_limit_l_max        39

_diffrn_reflns_theta_min          1.29

_diffrn_reflns_theta_max          28.20

_reflns_number_total              3070

_reflns_number_gt                 2777

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'Bruker SMART'

_computing_cell_refinement        'Bruker SMART'

_computing_data_reduction         'Bruker SAINT'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics     'Bruker SHELXTL'

_computing_publication_material   'Bruker SHELXTL'

 

_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)+(0.0370P)²+0.4220P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary      direct

_atom_sites_solution_secondary    difmap

_atom_sites_solution_hydrogens    geom

_refine_ls_hydrogen_treatment     ?

_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    0.03(8)

_refine_ls_number_reflns          3070

_refine_ls_number_parameters      181

_refine_ls_number_restraints      0

_refine_ls_R_factor_all           0.0395

_refine_ls_R_factor_gt            0.0335

_refine_ls_wR_factor_ref          0.0846

_refine_ls_wR_factor_gt           0.0760

_refine_ls_goodness_of_fit_ref    1.042

_refine_ls_restrained_S_all       1.042

_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 0.33376(16) 1.00249(6) 0.975179(17) 0.04268(15) Uani 1 1 d . . .

S2 S 0.96461(15) 0.64683(5) 0.837293(18) 0.03804(14) Uani 1 1 d . . .

C12 C 0.6929(5) 0.86307(18) 0.86638(6) 0.0291(4) Uani 1 1 d . . .

C13 C 0.7140(5) 0.87767(18) 0.82030(6) 0.0298(4) Uani 1 1 d . . .

C11 C 0.7962(6) 0.73751(19) 0.87883(6) 0.0333(5) Uani 1 1 d . . .

C7 C 0.5762(5) 0.94770(19) 0.89904(6) 0.0302(4) Uani 1 1 d . . .

C6 C 0.5185(6) 1.08808(18) 0.89975(6) 0.0323(4) Uani 1 1 d . . .

C15 C 0.9058(6) 0.7597(2) 0.75691(7) 0.0393(5) Uani 1 1 d . . .

H15A H 1.0145 0.6891 0.7449 0.047 Uiso 1 1 calc R . .

C18 C 0.5767(6) 0.97249(19) 0.79335(6) 0.0340(5) Uani 1 1 d . . .

H18A H 0.4614 1.0424 0.8048 0.041 Uiso 1 1 calc R . .

C14 C 0.8646(6) 0.76846(19) 0.80092(6) 0.0329(4) Uani 1 1 d . . .

C16 C 0.7826(6) 0.8574(2) 0.73170(7) 0.0414(5) Uani 1 1 d . . .

H16A H 0.8127 0.8537 0.7024 0.050 Uiso 1 1 calc R . .

C1 C 0.3778(6) 1.1288(2) 0.93867(7) 0.0361(5) Uani 1 1 d . . .

C8 C 0.5090(6) 0.89303(19) 0.93910(7) 0.0351(5) Uani 1 1 d . . .

C5 C 0.6142(6) 1.1843(2) 0.87068(7) 0.0377(5) Uani 1 1 d . . .

H5A H 0.7225 1.1615 0.8456 0.045 Uiso 1 1 calc R . .

C3 C 0.3874(7) 1.3497(2) 0.91681(9) 0.0503(6) Uani 1 1 d . . .

H3A H 0.3365 1.4363 0.9215 0.060 Uiso 1 1 calc R . .

C9 C 0.5895(6) 0.7643(2) 0.94947(7) 0.0389(5) Uani 1 1 d . . .

H9A H 0.5359 0.7310 0.9761 0.047 Uiso 1 1 calc R . .

C17 C 0.6132(6) 0.9617(2) 0.74958(7) 0.0384(5) Uani 1 1 d . . .

H17A H 0.5233 1.0251 0.7320 0.046 Uiso 1 1 calc R . .

C2 C 0.3041(7) 1.2592(2) 0.94684(8) 0.0462(6) Uani 1 1 d . . .

H2A H 0.2010 1.2837 0.9721 0.055 Uiso 1 1 calc R . .

C10 C 0.7471(6) 0.6886(2) 0.92008(7) 0.0386(5) Uani 1 1 d . . .

H10A H 0.8209 0.6060 0.9272 0.046 Uiso 1 1 calc R . .

C4 C 0.5469(7) 1.3137(2) 0.87940(8) 0.0465(6) Uani 1 1 d . . .

H4A H 0.6095 1.3769 0.8599 0.056 Uiso 1 1 calc R . .

 


 

_geom_special_details

;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;

 

loop_

 _geom_bond_atom_site_label_1

 _geom_bond_atom_site_label_2

 _geom_bond_distance

 _geom_bond_site_symmetry_2

 _geom_bond_publ_flag

S1 C1 1.748(2) . ?

S1 C8 1.749(2) . ?

S2 C11 1.744(2) . ?

S2 C14 1.746(2) . ?

C12 C11 1.417(3) . ?

C12 C7 1.428(3) . ?

C12 C13 1.461(3) . ?

C13 C18 1.408(3) . ?

C13 C14 1.417(3) . ?

C11 C10 1.407(3) . ?

C7 C8 1.407(3) . ?

C7 C6 1.469(3) . ?

C6 C5 1.404(3) . ?

C6 C1 1.412(3) . ?

C15 C16 1.375(3) . ?

C15 C14 1.398(3) . ?

C15 H15A 0.9300 . ?

C18 C17 1.390(3) . ?

C18 H18A 0.9300 . ?

C16 C17 1.392(3) . ?

C16 H16A 0.9300 . ?

C1 C2 1.404(3) . ?

C8 C9 1.407(3) . ?

C5 C4 1.391(3) . ?

C5 H5A 0.9300 . ?

C3 C2 1.370(4) . ?

C3 C4 1.390(4) . ?

C3 H3A 0.9300 . ?

C9 C10 1.365(3) . ?

C9 H9A 0.9300 . ?

C17 H17A 0.9300 . ?

C2 H2A 0.9300 . ?

C10 H10A 0.9300 . ?

C4 H4A 0.9300 . ?

 

loop_

 _geom_angle_atom_site_label_1

 _geom_angle_atom_site_label_2

 _geom_angle_atom_site_label_3

 _geom_angle

 _geom_angle_site_symmetry_1

 _geom_angle_site_symmetry_3

 _geom_angle_publ_flag

C1 S1 C8 90.91(10) . . ?

C11 S2 C14 90.93(10) . . ?

C11 C12 C7 117.20(18) . . ?

C11 C12 C13 110.62(18) . . ?

C7 C12 C13 132.10(19) . . ?

C18 C13 C14 117.44(18) . . ?

C18 C13 C12 130.37(19) . . ?

C14 C13 C12 111.70(18) . . ?

C10 C11 C12 122.9(2) . . ?

C10 C11 S2 123.54(16) . . ?

C12 C11 S2 113.42(16) . . ?

C8 C7 C12 117.47(18) . . ?

C8 C7 C6 110.66(18) . . ?

C12 C7 C6 131.84(19) . . ?

C5 C6 C1 117.58(18) . . ?

C5 C6 C7 130.3(2) . . ?

C1 C6 C7 111.71(18) . . ?

C16 C15 C14 118.8(2) . . ?

C16 C15 H15A 120.6 . . ?

C14 C15 H15A 120.6 . . ?

C17 C18 C13 120.1(2) . . ?

C17 C18 H18A 120.0 . . ?

C13 C18 H18A 120.0 . . ?

C15 C14 C13 121.9(2) . . ?

C15 C14 S2 125.18(17) . . ?

C13 C14 S2 112.85(15) . . ?

C15 C16 C17 120.6(2) . . ?

C15 C16 H16A 119.7 . . ?

C17 C16 H16A 119.7 . . ?

C2 C1 C6 121.9(2) . . ?

C2 C1 S1 125.15(18) . . ?

C6 C1 S1 112.83(16) . . ?

C7 C8 C9 122.9(2) . . ?

C7 C8 S1 113.47(15) . . ?

C9 C8 S1 123.53(17) . . ?

C4 C5 C6 120.0(2) . . ?

C4 C5 H5A 120.0 . . ?

C6 C5 H5A 120.0 . . ?

C2 C3 C4 120.9(2) . . ?

C2 C3 H3A 119.5 . . ?

C4 C3 H3A 119.5 . . ?

C10 C9 C8 119.3(2) . . ?

C10 C9 H9A 120.3 . . ?

C8 C9 H9A 120.3 . . ?

C18 C17 C16 120.9(2) . . ?

C18 C17 H17A 119.5 . . ?

C16 C17 H17A 119.5 . . ?

C3 C2 C1 118.5(2) . . ?

C3 C2 H2A 120.7 . . ?

C1 C2 H2A 120.7 . . ?

C9 C10 C11 118.9(2) . . ?

C9 C10 H10A 120.5 . . ?

C11 C10 H10A 120.5 . . ?

C3 C4 C5 120.8(2) . . ?

C3 C4 H4A 119.6 . . ?

C5 C4 H4A 119.6 . . ?

 

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

C11 C12 C13 C18 165.3(2) . . . . ?

C7 C12 C13 C18 -11.3(4) . . . . ?

C11 C12 C13 C14 -6.3(3) . . . . ?

C7 C12 C13 C14 177.1(2) . . . . ?

C7 C12 C11 C10 8.6(3) . . . . ?

C13 C12 C11 C10 -168.6(2) . . . . ?

C7 C12 C11 S2 -175.22(16) . . . . ?

C13 C12 C11 S2 7.6(2) . . . . ?

C14 S2 C11 C10 170.7(2) . . . . ?

C14 S2 C11 C12 -5.38(18) . . . . ?

C11 C12 C7 C8 -12.5(3) . . . . ?

C13 C12 C7 C8 164.0(2) . . . . ?

C11 C12 C7 C6 165.3(2) . . . . ?

C13 C12 C7 C6 -18.3(4) . . . . ?

C8 C7 C6 C5 165.7(2) . . . . ?

C12 C7 C6 C5 -12.2(4) . . . . ?

C8 C7 C6 C1 -6.3(3) . . . . ?

C12 C7 C6 C1 175.8(2) . . . . ?

C14 C13 C18 C17 -4.7(3) . . . . ?

C12 C13 C18 C17 -175.9(2) . . . . ?

C16 C15 C14 C13 -3.0(3) . . . . ?

C16 C15 C14 S2 172.96(19) . . . . ?

C18 C13 C14 C15 6.0(3) . . . . ?

C12 C13 C14 C15 178.8(2) . . . . ?

C18 C13 C14 S2 -170.40(17) . . . . ?

C12 C13 C14 S2 2.4(2) . . . . ?

C11 S2 C14 C15 -174.7(2) . . . . ?

C11 S2 C14 C13 1.61(18) . . . . ?

C14 C15 C16 C17 -1.4(4) . . . . ?

C5 C6 C1 C2 6.2(4) . . . . ?

C7 C6 C1 C2 179.3(2) . . . . ?

C5 C6 C1 S1 -170.12(18) . . . . ?

C7 C6 C1 S1 3.0(3) . . . . ?

C8 S1 C1 C2 -175.4(2) . . . . ?

C8 S1 C1 C6 0.77(19) . . . . ?

C12 C7 C8 C9 7.9(3) . . . . ?

C6 C7 C8 C9 -170.3(2) . . . . ?

C12 C7 C8 S1 -174.79(16) . . . . ?

C6 C7 C8 S1 7.0(3) . . . . ?

C1 S1 C8 C7 -4.58(19) . . . . ?

C1 S1 C8 C9 172.7(2) . . . . ?

C1 C6 C5 C4 -4.7(4) . . . . ?

C7 C6 C5 C4 -176.3(2) . . . . ?

C7 C8 C9 C10 1.6(4) . . . . ?

S1 C8 C9 C10 -175.43(18) . . . . ?

C13 C18 C17 C16 0.5(4) . . . . ?

C15 C16 C17 C18 2.7(4) . . . . ?

C4 C3 C2 C1 -1.2(4) . . . . ?

C6 C1 C2 C3 -3.3(4) . . . . ?

S1 C1 C2 C3 172.5(2) . . . . ?

C8 C9 C10 C11 -6.0(3) . . . . ?

C12 C11 C10 C9 0.8(4) . . . . ?

S2 C11 C10 C9 -174.94(18) . . . . ?

C2 C3 C4 C5 2.6(4) . . . . ?

C6 C5 C4 C3 0.5(4) . . . . ?

 

_diffrn_measured_fraction_theta_max    0.963

_diffrn_reflns_theta_full              28.20

_diffrn_measured_fraction_theta_full   0.963

_refine_diff_density_max    0.212

_refine_diff_density_min   -0.208

_refine_diff_density_rms    0.047

