 
data_2008src0842

#Dr. E. McDonald

#The thiophene ring was disordered over 2 main positions and
#restraints have been applied to ring atoms.

 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H19 N O5 S'
_chemical_formula_weight          397.43
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 '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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.5497(4)
_cell_length_b                    10.3189(4)
_cell_length_c                    11.1034(4)
_cell_angle_alpha                 104.436(2)
_cell_angle_beta                  107.828(2)
_cell_angle_gamma                 104.170(2)
_cell_volume                      945.55(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4177
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Block'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.396
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              416
_exptl_absorpt_coefficient_mu     0.205
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9449
_exptl_absorpt_correction_T_max   0.9759
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6443 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             21235
_diffrn_reflns_av_R_equivalents   0.0491
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.22
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4327
_reflns_number_gt                 3334
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0527P)²+0.3253P] 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_number_reflns          4327
_refine_ls_number_parameters      288
_refine_ls_number_restraints      52
_refine_ls_R_factor_all           0.0626
_refine_ls_R_factor_gt            0.0427
_refine_ls_wR_factor_ref          0.1126
_refine_ls_wR_factor_gt           0.1008
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.050
_refine_ls_shift/su_max           0.004
_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 0.14843(17) 0.68649(16) 0.48821(15) 0.0170(3) Uani 1 1 d . . .
C2 C 0.06360(17) 0.84511(16) 0.39416(15) 0.0166(3) Uani 1 1 d . . .
C3 C -0.06573(17) 0.70095(16) 0.31323(15) 0.0170(3) Uani 1 1 d . . .
H3 H -0.1689 0.7013 0.3172 0.020 Uiso 1 1 calc R . .
C4 C -0.00728(17) 0.59573(15) 0.37293(15) 0.0168(3) Uani 1 1 d . A .
H4 H -0.0833 0.5426 0.4040 0.020 Uiso 1 1 calc R . .
C5 C 0.00697(18) 0.49489(16) 0.24972(15) 0.0181(3) Uani 1 1 d D . .
C6 C -0.16128(18) 0.39766(16) 0.14867(16) 0.0215(3) Uani 1 1 d . A .
H6A H -0.2258 0.3594 0.1952 0.026 Uiso 1 1 calc R . .
H6B H -0.1603 0.3174 0.0784 0.026 Uiso 1 1 calc R . .
C7 C -0.22105(19) 0.50330(17) 0.08797(16) 0.0222(3) Uani 1 1 d . . .
H7A H -0.2470 0.4730 -0.0105 0.027 Uiso 1 1 calc R A .
H7B H -0.3141 0.5137 0.1054 0.027 Uiso 1 1 calc R . .
C8 C -0.07774(17) 0.64216(16) 0.16568(15) 0.0177(3) Uani 1 1 d . A .
C9 C -0.06551(18) 0.75102(16) 0.09632(15) 0.0187(3) Uani 1 1 d . . .
C10 C -0.1961(2) 0.8962(2) 0.01050(19) 0.0300(4) Uani 1 1 d . . .
H10A H -0.1798 0.8681 -0.0748 0.036 Uiso 1 1 calc R A .
H10B H -0.1106 0.9867 0.0736 0.036 Uiso 1 1 calc R . .
C11 C -0.3518(3) 0.9152(3) -0.0164(3) 0.0621(8) Uani 1 1 d . A .
H11A H -0.4355 0.8247 -0.0781 0.093 Uiso 1 1 calc R . .
H11B H -0.3559 0.9886 -0.0575 0.093 Uiso 1 1 calc R . .
H11C H -0.3658 0.9446 0.0688 0.093 Uiso 1 1 calc R . .
C12 C 0.32314(17) 0.94255(15) 0.58839(15) 0.0166(3) Uani 1 1 d . . .
C13 C 0.46747(18) 0.92683(16) 0.60758(15) 0.0194(3) Uani 1 1 d . . .
H13 H 0.4737 0.8400 0.5589 0.023 Uiso 1 1 calc R . .
C14 C 0.60243(18) 1.03935(17) 0.69862(16) 0.0207(3) Uani 1 1 d . . .
H14 H 0.7018 1.0289 0.7138 0.025 Uiso 1 1 calc R . .
C15 C 0.59403(19) 1.16725(17) 0.76792(16) 0.0213(3) Uani 1 1 d . . .
H15 H 0.6873 1.2450 0.8281 0.026 Uiso 1 1 calc R . .
C16 C 0.44902(19) 1.18091(17) 0.74889(17) 0.0264(4) Uani 1 1 d . . .
H16 H 0.4430 1.2681 0.7969 0.032 Uiso 1 1 calc R . .
C17 C 0.31207(19) 1.06791(17) 0.65996(17) 0.0231(4) Uani 1 1 d . . .
H17 H 0.2124 1.0765 0.6484 0.028 Uiso 1 1 calc R . .
N1 N 0.18233(14) 0.82784(13) 0.49234(12) 0.0164(3) Uani 1 1 d . . .
O1 O 0.23249(13) 0.64817(11) 0.56719(11) 0.0216(3) Uani 1 1 d . . .
O2 O 0.06534(12) 0.95673(11) 0.37680(11) 0.0206(3) Uani 1 1 d . . .
O3 O 0.05319(12) 0.59288(11) 0.18375(10) 0.0179(2) Uani 1 1 d . A .
O4 O 0.04415(13) 0.80059(12) 0.07003(11) 0.0244(3) Uani 1 1 d . A .
O5 O -0.19572(13) 0.78436(12) 0.06994(11) 0.0237(3) Uani 1 1 d . A .
S1 S 0.3116(3) 0.4923(3) 0.2981(3) 0.0242(4) Uani 0.494(3) 1 d PD A 1
C18 C 0.122(8) 0.421(8) 0.283(9) 0.0189(6) Uani 0.494(3) 1 d PDU A 1
C19 C 0.356(2) 0.378(2) 0.346(3) 0.0224(16) Uani 0.494(3) 1 d PDU A 1
H19 H 0.4626 0.3854 0.3692 0.027 Uiso 0.494(3) 1 calc PR A 1
C20 C 0.261(2) 0.266(2) 0.360(2) 0.021(2) Uani 0.494(3) 1 d PDU A 1
H20 H 0.2810 0.1888 0.3859 0.026 Uiso 0.494(3) 1 calc PR A 1
C21 C 0.1043(10) 0.3041(8) 0.3192(10) 0.0301(18) Uani 0.494(3) 1 d PDU A 1
H21 H 0.0088 0.2505 0.3205 0.036 Uiso 0.494(3) 1 calc PR A 1
S2 S 0.0686(2) 0.26904(19) 0.3210(2) 0.0216(4) Uani 0.506(3) 1 d PDU A 2
C118 C 0.123(8) 0.422(8) 0.284(9) 0.0189(6) Uani 0.506(3) 1 d PDU A 2
C119 C 0.2354(19) 0.266(2) 0.361(2) 0.022(3) Uani 0.506(3) 1 d PD A 2
H119 H 0.2545 0.1946 0.3966 0.026 Uiso 0.506(3) 1 calc PR A 2
C120 C 0.360(2) 0.355(2) 0.352(3) 0.0224(16) Uani 0.506(3) 1 d PD A 2
H120 H 0.4638 0.3551 0.3688 0.027 Uiso 0.506(3) 1 calc PR A 2
C121 C 0.2761(11) 0.4598(10) 0.3021(12) 0.037(3) Uani 0.506(3) 1 d PD A 2
H121 H 0.3287 0.5410 0.2865 0.044 Uiso 0.506(3) 1 calc PR A 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 1.2112(18) . ?
C1 N1 1.4003(19) . ?
C1 C4 1.510(2) . ?
C2 O2 1.2114(18) . ?
C2 N1 1.3945(19) . ?
C2 C3 1.517(2) . ?
C3 C4 1.536(2) . ?
C3 C8 1.556(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.564(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.4499(18) . ?
C5 C18 1.490(9) . ?
C5 C118 1.496(8) . ?
C5 C6 1.547(2) . ?
C6 C7 1.550(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.540(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.4390(17) . ?
C8 C9 1.513(2) . ?
C9 O4 1.2012(19) . ?
C9 O5 1.3368(18) . ?
C10 O5 1.4653(19) . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.385(2) . ?
C12 C17 1.386(2) . ?
C12 N1 1.4352(19) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
S1 C19 1.506(16) . ?
S1 C18 1.72(9) . ?
C18 C21 1.36(8) . ?
C19 C20 1.363(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.601(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
S2 C119 1.527(15) . ?
S2 C118 1.72(9) . ?
C118 C121 1.35(8) . ?
C119 C120 1.365(11) . ?
C119 H119 0.9500 . ?
C120 C121 1.600(17) . ?
C120 H120 0.9500 . ?
C121 H121 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
O1 C1 N1 123.84(14) . . ?
O1 C1 C4 127.49(14) . . ?
N1 C1 C4 108.67(12) . . ?
O2 C2 N1 125.28(14) . . ?
O2 C2 C3 126.32(14) . . ?
N1 C2 C3 108.40(12) . . ?
C2 C3 C4 105.23(12) . . ?
C2 C3 C8 112.33(12) . . ?
C4 C3 C8 101.56(11) . . ?
C2 C3 H3 112.3 . . ?
C4 C3 H3 112.3 . . ?
C8 C3 H3 112.3 . . ?
C1 C4 C3 104.99(12) . . ?
C1 C4 C5 113.84(12) . . ?
C3 C4 C5 101.65(11) . . ?
C1 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
C5 C4 H4 111.9 . . ?
O3 C5 C18 111(4) . . ?
O3 C5 C118 111(4) . . ?
C18 C5 C118 1(7) . . ?
O3 C5 C6 103.01(12) . . ?
C18 C5 C6 116(3) . . ?
C118 C5 C6 116(3) . . ?
O3 C5 C4 101.68(11) . . ?
C18 C5 C4 116(4) . . ?
C118 C5 C4 115(4) . . ?
C6 C5 C4 107.44(12) . . ?
C5 C6 C7 101.47(12) . . ?
C5 C6 H6A 111.5 . . ?
C7 C6 H6A 111.5 . . ?
C5 C6 H6B 111.5 . . ?
C7 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
C8 C7 C6 101.45(12) . . ?
C8 C7 H7A 111.5 . . ?
C6 C7 H7A 111.5 . . ?
C8 C7 H7B 111.5 . . ?
C6 C7 H7B 111.5 . . ?
H7A C7 H7B 109.3 . . ?
O3 C8 C9 110.85(12) . . ?
O3 C8 C7 103.32(11) . . ?
C9 C8 C7 115.76(13) . . ?
O3 C8 C3 101.98(11) . . ?
C9 C8 C3 114.85(12) . . ?
C7 C8 C3 108.59(12) . . ?
O4 C9 O5 125.31(14) . . ?
O4 C9 C8 125.53(14) . . ?
O5 C9 C8 109.17(12) . . ?
O5 C10 C11 107.68(15) . . ?
O5 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O5 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 121.10(14) . . ?
C13 C12 N1 119.71(13) . . ?
C17 C12 N1 119.19(13) . . ?
C14 C13 C12 119.07(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.67(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.62(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.47(14) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.02(14) . . ?
C12 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C2 N1 C1 112.65(12) . . ?
C2 N1 C12 123.79(12) . . ?
C1 N1 C12 123.56(12) . . ?
C8 O3 C5 96.99(10) . . ?
C9 O5 C10 115.24(12) . . ?
C19 S1 C18 92(2) . . ?
C21 C18 C5 128(7) . . ?
C21 C18 S1 110.0(11) . . ?
C5 C18 S1 122(6) . . ?
C20 C19 S1 128(2) . . ?
C20 C19 H19 116.2 . . ?
S1 C19 H19 116.2 . . ?
C19 C20 C21 97.6(18) . . ?
C19 C20 H20 131.2 . . ?
C21 C20 H20 131.2 . . ?
C18 C21 C20 113(3) . . ?
C18 C21 H21 123.5 . . ?
C20 C21 H21 123.5 . . ?
C119 S2 C118 91.3(18) . . ?
C121 C118 C5 131(7) . . ?
C121 C118 S2 110.0(13) . . ?
C5 C118 S2 119(6) . . ?
C120 C119 S2 127.2(17) . . ?
C120 C119 H119 116.4 . . ?
S2 C119 H119 116.4 . . ?
C119 C120 C121 97.6(17) . . ?
C119 C120 H120 131.2 . . ?
C121 C120 H120 131.2 . . ?
C118 C121 C120 114(3) . . ?
C118 C121 H121 123.2 . . ?
C120 C121 H121 123.2 . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.243
_refine_diff_density_min   -0.276
_refine_diff_density_rms    0.059
