 
data_2007src1053 
#Dr Adrian Dobbs 

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H30 Cl N O2 S' 
_chemical_formula_weight          383.96 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic  
_symmetry_space_group_name_H-M     Pbca 
 
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' 
 '-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                    13.0538(3) 
_cell_length_b                    15.5288(3) 
_cell_length_c                    19.1088(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3873.54(14) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     28447
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        Wedge 
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.60 
_exptl_crystal_size_mid           0.50 
_exptl_crystal_size_min           0.50 
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.317 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1648 
_exptl_absorpt_coefficient_mu     0.319 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.8318 
_exptl_absorpt_correction_T_max   0.8569 
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details 
; 
 SADABS was used to perform the Absorption correction 
Estimated minimum and maximum transmission: 0.6628  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             31418 
_diffrn_reflns_av_R_equivalents   0.0516 
_diffrn_reflns_av_sigmaI/netI     0.0367 
_diffrn_reflns_limit_h_min        -16 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          2.95 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              4422 
_reflns_number_gt                 3598 
_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, 1990)' 
_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)+(0.0508P)²+3.0009P] 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          4422 
_refine_ls_number_parameters      228 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0550 
_refine_ls_R_factor_gt            0.0406 
_refine_ls_wR_factor_ref          0.1096 
_refine_ls_wR_factor_gt           0.1017 
_refine_ls_goodness_of_fit_ref    1.025 
_refine_ls_restrained_S_all       1.025 
_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 0.27994(3) 0.82924(3) 0.09615(2) 0.01605(12) Uani 1 1 d . . . 
Cl1 Cl 0.06250(4) 0.99941(3) 0.19543(3) 0.03027(14) Uani 1 1 d . . . 
O1 O 0.29179(10) 0.80925(8) 0.02315(6) 0.0224(3) Uani 1 1 d . . . 
O2 O 0.35020(10) 0.79336(8) 0.14609(7) 0.0231(3) Uani 1 1 d . . . 
N1 N 0.28751(11) 0.93277(9) 0.10536(7) 0.0162(3) Uani 1 1 d . . . 
C16 C 0.02929(14) 0.76017(12) 0.20594(9) 0.0206(4) Uani 1 1 d . . . 
H16 H 0.0095 0.7569 0.2537 0.025 Uiso 1 1 calc R . . 
C14 C 0.15544(13) 0.79484(10) 0.11896(8) 0.0150(3) Uani 1 1 d . . . 
C18 C -0.01109(14) 0.74468(12) 0.08428(9) 0.0215(4) Uani 1 1 d . . . 
H18 H -0.0580 0.7296 0.0483 0.026 Uiso 1 1 calc R . . 
C15 C 0.12725(14) 0.78777(11) 0.18905(9) 0.0181(4) Uani 1 1 d . . . 
H15 H 0.1747 0.8017 0.2250 0.022 Uiso 1 1 calc R . . 
C2 C 0.21094(13) 1.07306(11) 0.11083(9) 0.0171(4) Uani 1 1 d . . . 
H2 H 0.2284 1.1240 0.0811 0.020 Uiso 1 1 calc R . . 
C9 C 0.19325(14) 1.06192(12) -0.05547(9) 0.0199(4) Uani 1 1 d . . . 
H9A H 0.1260 1.0327 -0.0578 0.024 Uiso 1 1 calc R . . 
H9B H 0.1827 1.1195 -0.0344 0.024 Uiso 1 1 calc R . . 
C17 C -0.04067(14) 0.73708(11) 0.15399(9) 0.0195(4) Uani 1 1 d . . . 
C3 C 0.29644(14) 1.06412(12) 0.16551(10) 0.0218(4) Uani 1 1 d . . . 
H3A H 0.3602 1.0918 0.1487 0.026 Uiso 1 1 calc R . . 
H3B H 0.2759 1.0915 0.2102 0.026 Uiso 1 1 calc R . . 
C8 C 0.26627(14) 1.00927(11) -0.00936(8) 0.0167(4) Uani 1 1 d . . . 
H8 H 0.2758 0.9521 -0.0326 0.020 Uiso 1 1 calc R . . 
C19 C 0.08588(14) 0.77401(11) 0.06657(9) 0.0189(4) Uani 1 1 d . . . 
H19 H 0.1047 0.7798 0.0188 0.023 Uiso 1 1 calc R . . 
C6 C 0.02198(14) 1.11023(12) 0.08808(9) 0.0216(4) Uani 1 1 d . . . 
H6A H 0.0469 1.1571 0.0573 0.026 Uiso 1 1 calc R . . 
H6B H 0.0107 1.0588 0.0585 0.026 Uiso 1 1 calc R . . 
C5 C 0.10449(14) 1.08971(11) 0.14181(9) 0.0204(4) Uani 1 1 d . . . 
H5 H 0.1105 1.1408 0.1734 0.024 Uiso 1 1 calc R . . 
C4 C 0.31261(15) 0.96777(12) 0.17553(9) 0.0220(4) Uani 1 1 d . . . 
H4A H 0.3843 0.9548 0.1886 0.026 Uiso 1 1 calc R . . 
H4B H 0.2661 0.9444 0.2118 0.026 Uiso 1 1 calc R . . 
C1 C 0.22052(13) 0.99197(11) 0.06362(8) 0.0155(3) Uani 1 1 d . . . 
H1 H 0.1514 0.9651 0.0581 0.019 Uiso 1 1 calc R . . 
C7 C -0.07971(15) 1.13724(14) 0.11974(11) 0.0283(4) Uani 1 1 d . . . 
H7A H -0.1027 1.0932 0.1529 0.042 Uiso 1 1 calc R . . 
H7B H -0.1307 1.1437 0.0825 0.042 Uiso 1 1 calc R . . 
H7C H -0.0713 1.1922 0.1442 0.042 Uiso 1 1 calc R . . 
C20 C -0.14477(15) 0.70211(14) 0.17307(11) 0.0294(4) Uani 1 1 d . . . 
H20A H -0.1390 0.6406 0.1840 0.044 Uiso 1 1 calc R . . 
H20B H -0.1918 0.7100 0.1336 0.044 Uiso 1 1 calc R . . 
H20C H -0.1711 0.7330 0.2140 0.044 Uiso 1 1 calc R . . 
C13 C 0.37102(14) 1.05303(12) -0.00712(9) 0.0221(4) Uani 1 1 d . . . 
H13A H 0.4186 1.0179 0.0214 0.027 Uiso 1 1 calc R . . 
H13B H 0.3644 1.1101 0.0154 0.027 Uiso 1 1 calc R . . 
C11 C 0.34173(16) 1.11425(14) -0.12776(10) 0.0307(5) Uani 1 1 d . . . 
H11A H 0.3353 1.1740 -0.1103 0.037 Uiso 1 1 calc R . . 
H11B H 0.3699 1.1167 -0.1758 0.037 Uiso 1 1 calc R . . 
C10 C 0.23645(15) 1.07225(13) -0.12947(9) 0.0256(4) Uani 1 1 d . . . 
H10A H 0.2416 1.0150 -0.1520 0.031 Uiso 1 1 calc R . . 
H10B H 0.1892 1.1081 -0.1577 0.031 Uiso 1 1 calc R . . 
C12 C 0.41504(15) 1.06417(14) -0.08074(10) 0.0282(4) Uani 1 1 d . . . 
H12A H 0.4812 1.0952 -0.0779 0.034 Uiso 1 1 calc R . . 
H12B H 0.4282 1.0068 -0.1015 0.034 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 O2 1.4360(13) . ? 
S1 O1 1.4376(13) . ? 
S1 N1 1.6203(15) . ? 
S1 C14 1.7654(17) . ? 
Cl1 C5 1.8212(18) . ? 
N1 C4 1.483(2) . ? 
N1 C1 1.499(2) . ? 
C16 C15 1.387(3) . ? 
C16 C17 1.396(3) . ? 
C16 H16 0.9500 . ? 
C14 C19 1.390(2) . ? 
C14 C15 1.393(2) . ? 
C18 C19 1.387(3) . ? 
C18 C17 1.392(2) . ? 
C18 H18 0.9500 . ? 
C15 H15 0.9500 . ? 
C2 C5 1.532(2) . ? 
C2 C3 1.535(2) . ? 
C2 C1 1.554(2) . ? 
C2 H2 1.0000 . ? 
C9 C10 1.531(2) . ? 
C9 C8 1.534(2) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C17 C20 1.508(3) . ? 
C3 C4 1.523(3) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
C8 C13 1.527(3) . ? 
C8 C1 1.541(2) . ? 
C8 H8 1.0000 . ? 
C19 H19 0.9500 . ? 
C6 C7 1.518(3) . ? 
C6 C5 1.522(3) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C5 H5 1.0000 . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C1 H1 1.0000 . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
C13 C12 1.529(2) . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C11 C10 1.522(3) . ? 
C11 C12 1.526(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C12 H12A 0.9900 . ? 
C12 H12B 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 
O2 S1 O1 119.50(8) . . ? 
O2 S1 N1 105.89(8) . . ? 
O1 S1 N1 108.24(7) . . ? 
O2 S1 C14 107.85(8) . . ? 
O1 S1 C14 105.86(8) . . ? 
N1 S1 C14 109.24(8) . . ? 
C4 N1 C1 112.66(13) . . ? 
C4 N1 S1 118.37(11) . . ? 
C1 N1 S1 121.01(11) . . ? 
C15 C16 C17 121.15(16) . . ? 
C15 C16 H16 119.4 . . ? 
C17 C16 H16 119.4 . . ? 
C19 C14 C15 120.10(16) . . ? 
C19 C14 S1 119.62(13) . . ? 
C15 C14 S1 120.28(13) . . ? 
C19 C18 C17 120.96(16) . . ? 
C19 C18 H18 119.5 . . ? 
C17 C18 H18 119.5 . . ? 
C16 C15 C14 119.45(16) . . ? 
C16 C15 H15 120.3 . . ? 
C14 C15 H15 120.3 . . ? 
C5 C2 C3 114.30(14) . . ? 
C5 C2 C1 115.71(14) . . ? 
C3 C2 C1 105.27(13) . . ? 
C5 C2 H2 107.0 . . ? 
C3 C2 H2 107.0 . . ? 
C1 C2 H2 107.0 . . ? 
C10 C9 C8 110.95(15) . . ? 
C10 C9 H9A 109.4 . . ? 
C8 C9 H9A 109.4 . . ? 
C10 C9 H9B 109.4 . . ? 
C8 C9 H9B 109.4 . . ? 
H9A C9 H9B 108.0 . . ? 
C18 C17 C16 118.51(17) . . ? 
C18 C17 C20 120.78(17) . . ? 
C16 C17 C20 120.68(16) . . ? 
C4 C3 C2 105.97(14) . . ? 
C4 C3 H3A 110.5 . . ? 
C2 C3 H3A 110.5 . . ? 
C4 C3 H3B 110.5 . . ? 
C2 C3 H3B 110.5 . . ? 
H3A C3 H3B 108.7 . . ? 
C13 C8 C9 109.58(14) . . ? 
C13 C8 C1 113.54(14) . . ? 
C9 C8 C1 111.84(14) . . ? 
C13 C8 H8 107.2 . . ? 
C9 C8 H8 107.2 . . ? 
C1 C8 H8 107.2 . . ? 
C18 C19 C14 119.80(16) . . ? 
C18 C19 H19 120.1 . . ? 
C14 C19 H19 120.1 . . ? 
C7 C6 C5 114.08(15) . . ? 
C7 C6 H6A 108.7 . . ? 
C5 C6 H6A 108.7 . . ? 
C7 C6 H6B 108.7 . . ? 
C5 C6 H6B 108.7 . . ? 
H6A C6 H6B 107.6 . . ? 
C6 C5 C2 114.62(14) . . ? 
C6 C5 Cl1 109.13(13) . . ? 
C2 C5 Cl1 111.13(12) . . ? 
C6 C5 H5 107.2 . . ? 
C2 C5 H5 107.2 . . ? 
Cl1 C5 H5 107.2 . . ? 
N1 C4 C3 102.46(14) . . ? 
N1 C4 H4A 111.3 . . ? 
C3 C4 H4A 111.3 . . ? 
N1 C4 H4B 111.3 . . ? 
C3 C4 H4B 111.3 . . ? 
H4A C4 H4B 109.2 . . ? 
N1 C1 C8 111.26(14) . . ? 
N1 C1 C2 103.59(13) . . ? 
C8 C1 C2 114.53(13) . . ? 
N1 C1 H1 109.1 . . ? 
C8 C1 H1 109.1 . . ? 
C2 C1 H1 109.1 . . ? 
C6 C7 H7A 109.5 . . ? 
C6 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
C6 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
C17 C20 H20A 109.5 . . ? 
C17 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
C17 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C8 C13 C12 111.16(15) . . ? 
C8 C13 H13A 109.4 . . ? 
C12 C13 H13A 109.4 . . ? 
C8 C13 H13B 109.4 . . ? 
C12 C13 H13B 109.4 . . ? 
H13A C13 H13B 108.0 . . ? 
C10 C11 C12 111.14(16) . . ? 
C10 C11 H11A 109.4 . . ? 
C12 C11 H11A 109.4 . . ? 
C10 C11 H11B 109.4 . . ? 
C12 C11 H11B 109.4 . . ? 
H11A C11 H11B 108.0 . . ? 
C11 C10 C9 110.96(16) . . ? 
C11 C10 H10A 109.4 . . ? 
C9 C10 H10A 109.4 . . ? 
C11 C10 H10B 109.4 . . ? 
C9 C10 H10B 109.4 . . ? 
H10A C10 H10B 108.0 . . ? 
C11 C12 C13 111.32(16) . . ? 
C11 C12 H12A 109.4 . . ? 
C13 C12 H12A 109.4 . . ? 
C11 C12 H12B 109.4 . . ? 
C13 C12 H12B 109.4 . . ? 
H12A C12 H12B 108.0 . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.875 
_refine_diff_density_min   -0.417 
_refine_diff_density_rms    0.059 
