 
data_2007src1052 
# Dr A Dobbs
# The crystal was a mixture of enantiomers (~ 44% seen as flack parameter)
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H28 Cl N O2 S' 
_chemical_formula_weight          405.96 
 
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            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                    8.9411(3) 
_cell_length_b                    11.0719(3) 
_cell_length_c                    10.9373(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  99.810(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1066.91(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used   12241 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description       Block 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.60 
_exptl_crystal_size_mid           0.50 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas      'not measured' 
_exptl_crystal_density_diffrn     1.264 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              432 
_exptl_absorpt_coefficient_mu     0.293 
_exptl_absorpt_correction_type   multi-scan 
_exptl_absorpt_correction_T_min   0.8436 
_exptl_absorpt_correction_T_max   0.9171 
_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: 0.6543 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             13213 
_diffrn_reflns_av_R_equivalents   0.0367 
_diffrn_reflns_av_sigmaI/netI     0.0443 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.23 
_diffrn_reflns_theta_max          27.47 
_reflns_number_total              4663 
_reflns_number_gt                 4248 
_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)+(0.0566P)²+0.1765P] 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    0.44(6)
 _chemical_absolute_configuration   unk
_refine_ls_number_reflns          4663 
_refine_ls_number_parameters      247 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0470 
_refine_ls_R_factor_gt            0.0404 
_refine_ls_wR_factor_ref          0.1078 
_refine_ls_wR_factor_gt           0.1043 
_refine_ls_goodness_of_fit_ref    1.121 
_refine_ls_restrained_S_all       1.121 
_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 1.13593(7) -0.00421(5) 0.66579(6) 0.02739(14) Uani 1 1 d . . . 
Cl1 Cl 0.51558(7) 0.13204(6) 0.38166(6) 0.03947(17) Uani 1 1 d . . . 
C1 C 0.7071(3) 0.1502(2) 0.4660(2) 0.0267(5) Uani 1 1 d . . . 
H1 H 0.7301 0.2386 0.4697 0.032 Uiso 1 1 calc R . . 
C2 C 0.8190(3) 0.0904(2) 0.3958(2) 0.0319(6) Uani 1 1 d . . . 
H2A H 0.8088 0.1253 0.3114 0.038 Uiso 1 1 calc R . . 
H2B H 0.7974 0.0028 0.3876 0.038 Uiso 1 1 calc R . . 
C3 C 0.9800(3) 0.1101(2) 0.4653(2) 0.0286(5) Uani 1 1 d . . . 
H3A H 1.0535 0.0656 0.4240 0.034 Uiso 1 1 calc R . . 
H3B H 1.0060 0.1970 0.4666 0.034 Uiso 1 1 calc R . . 
N1 N 0.9857(2) 0.06478(17) 0.59373(17) 0.0224(4) Uani 1 1 d . . . 
C4 C 0.8837(2) 0.1256(2) 0.66729(18) 0.0197(4) Uani 1 1 d . . . 
H4 H 0.8949 0.0838 0.7494 0.024 Uiso 1 1 calc R . . 
C5 C 0.7190(2) 0.10528(19) 0.59990(18) 0.0210(4) Uani 1 1 d . . . 
H5 H 0.6517 0.1578 0.6415 0.025 Uiso 1 1 calc R . . 
C6 C 0.6678(3) -0.0254(2) 0.6126(2) 0.0260(5) Uani 1 1 d . . . 
H6A H 0.5712 -0.0388 0.5550 0.031 Uiso 1 1 calc R . . 
H6B H 0.7447 -0.0805 0.5881 0.031 Uiso 1 1 calc R . . 
C7 C 0.6453(3) -0.0562(2) 0.7444(2) 0.0287(5) Uani 1 1 d . . . 
H7A H 0.7440 -0.0575 0.7994 0.043 Uiso 1 1 calc R . . 
H7B H 0.5973 -0.1357 0.7448 0.043 Uiso 1 1 calc R . . 
H7C H 0.5802 0.0048 0.7735 0.043 Uiso 1 1 calc R . . 
C8 C 0.9243(2) 0.25951(19) 0.69222(19) 0.0199(4) Uani 1 1 d . . . 
H8A H 1.0361 0.2689 0.7062 0.024 Uiso 1 1 calc R . . 
H8B H 0.8816 0.3079 0.6183 0.024 Uiso 1 1 calc R . . 
C9 C 0.8632(3) 0.3074(2) 0.8048(2) 0.0345(6) Uani 1 1 d . . . 
H9A H 0.7509 0.3065 0.7870 0.041 Uiso 1 1 calc R . . 
H9B H 0.8963 0.2533 0.8764 0.041 Uiso 1 1 calc R . . 
C10 C 0.9169(3) 0.4336(2) 0.83856(19) 0.0229(5) Uani 1 1 d . . . 
C11 C 1.0540(3) 0.4544(2) 0.9176(2) 0.0275(5) Uani 1 1 d . . . 
H11 H 1.1110 0.3877 0.9554 0.033 Uiso 1 1 calc R . . 
C12 C 1.1083(3) 0.5697(2) 0.9420(2) 0.0323(6) Uani 1 1 d . . . 
H12 H 1.2024 0.5818 0.9957 0.039 Uiso 1 1 calc R . . 
C13 C 1.0264(4) 0.6687(2) 0.8887(2) 0.0370(7) Uani 1 1 d . . . 
H13 H 1.0644 0.7483 0.9048 0.044 Uiso 1 1 calc R . . 
C14 C 0.8887(3) 0.6497(2) 0.8116(2) 0.0371(6) Uani 1 1 d . . . 
H14 H 0.8309 0.7165 0.7753 0.045 Uiso 1 1 calc R . . 
C15 C 0.8351(3) 0.5333(2) 0.7876(2) 0.0318(6) Uani 1 1 d . . . 
H15 H 0.7402 0.5214 0.7350 0.038 Uiso 1 1 calc R . . 
C16 C 1.2541(2) 0.1069(2) 0.7481(2) 0.0238(5) Uani 1 1 d . . . 
C17 C 1.3274(2) 0.1890(2) 0.6821(2) 0.0260(5) Uani 1 1 d . . . 
H17 H 1.3211 0.1808 0.5950 0.031 Uiso 1 1 calc R . . 
C18 C 1.4099(3) 0.2832(2) 0.7452(2) 0.0278(5) Uani 1 1 d . . . 
H18 H 1.4577 0.3408 0.7002 0.033 Uiso 1 1 calc R . . 
C19 C 1.4234(3) 0.2941(2) 0.8740(2) 0.0304(5) Uani 1 1 d . . . 
C20 C 1.3511(3) 0.2088(3) 0.9375(2) 0.0320(5) Uani 1 1 d . . . 
H20 H 1.3611 0.2143 1.0253 0.038 Uiso 1 1 calc R . . 
C22 C 1.5119(3) 0.3964(3) 0.9432(3) 0.0488(8) Uani 1 1 d . . . 
H22A H 1.6104 0.3663 0.9852 0.073 Uiso 1 1 calc R . . 
H22B H 1.4550 0.4290 1.0048 0.073 Uiso 1 1 calc R . . 
H22C H 1.5276 0.4601 0.8845 0.073 Uiso 1 1 calc R . . 
C21 C 1.2652(3) 0.1166(2) 0.8762(2) 0.0271(5) Uani 1 1 d . . . 
H21 H 1.2145 0.0607 0.9208 0.032 Uiso 1 1 calc R . . 
O1 O 1.2130(2) -0.05397(17) 0.57177(19) 0.0415(5) Uani 1 1 d . . . 
O2 O 1.0872(2) -0.08184(16) 0.75612(19) 0.0388(5) 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 
S1 O2 1.4321(19) . ? 
S1 O1 1.4414(19) . ? 
S1 N1 1.6271(19) . ? 
S1 C16 1.765(2) . ? 
Cl1 C1 1.812(2) . ? 
C1 C2 1.514(4) . ? 
C1 C5 1.533(3) . ? 
C1 H1 1.0000 . ? 
C2 C3 1.525(3) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 N1 1.484(3) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
N1 C4 1.477(3) . ? 
C4 C8 1.539(3) . ? 
C4 C5 1.547(3) . ? 
C4 H4 1.0000 . ? 
C5 C6 1.531(3) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.528(3) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
C8 C9 1.525(3) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C10 1.504(3) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 C15 1.387(3) . ? 
C10 C11 1.394(3) . ? 
C11 C12 1.376(4) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.390(4) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.384(4) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.384(4) . ? 
C14 H14 0.9500 . ? 
C15 H15 0.9500 . ? 
C16 C17 1.392(3) . ? 
C16 C21 1.392(3) . ? 
C17 C18 1.391(3) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.399(3) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.396(4) . ? 
C19 C22 1.508(3) . ? 
C20 C21 1.380(4) . ? 
C20 H20 0.9500 . ? 
C22 H22A 0.9800 . ? 
C22 H22B 0.9800 . ? 
C22 H22C 0.9800 . ? 
C21 H21 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 
O2 S1 O1 120.08(12) . . ? 
O2 S1 N1 107.05(11) . . ? 
O1 S1 N1 106.82(11) . . ? 
O2 S1 C16 107.00(11) . . ? 
O1 S1 C16 108.23(11) . . ? 
N1 S1 C16 107.02(10) . . ? 
C2 C1 C5 113.48(19) . . ? 
C2 C1 Cl1 110.01(15) . . ? 
C5 C1 Cl1 110.86(16) . . ? 
C2 C1 H1 107.4 . . ? 
C5 C1 H1 107.4 . . ? 
Cl1 C1 H1 107.4 . . ? 
C1 C2 C3 109.51(18) . . ? 
C1 C2 H2A 109.8 . . ? 
C3 C2 H2A 109.8 . . ? 
C1 C2 H2B 109.8 . . ? 
C3 C2 H2B 109.8 . . ? 
H2A C2 H2B 108.2 . . ? 
N1 C3 C2 107.55(19) . . ? 
N1 C3 H3A 110.2 . . ? 
C2 C3 H3A 110.2 . . ? 
N1 C3 H3B 110.2 . . ? 
C2 C3 H3B 110.2 . . ? 
H3A C3 H3B 108.5 . . ? 
C4 N1 C3 115.86(18) . . ? 
C4 N1 S1 119.03(14) . . ? 
C3 N1 S1 120.65(16) . . ? 
N1 C4 C8 112.75(18) . . ? 
N1 C4 C5 107.47(16) . . ? 
C8 C4 C5 113.64(17) . . ? 
N1 C4 H4 107.6 . . ? 
C8 C4 H4 107.6 . . ? 
C5 C4 H4 107.6 . . ? 
C6 C5 C1 114.85(18) . . ? 
C6 C5 C4 111.67(18) . . ? 
C1 C5 C4 108.26(18) . . ? 
C6 C5 H5 107.2 . . ? 
C1 C5 H5 107.2 . . ? 
C4 C5 H5 107.2 . . ? 
C7 C6 C5 112.73(19) . . ? 
C7 C6 H6A 109.0 . . ? 
C5 C6 H6A 109.0 . . ? 
C7 C6 H6B 109.0 . . ? 
C5 C6 H6B 109.0 . . ? 
H6A C6 H6B 107.8 . . ? 
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 . . ? 
C9 C8 C4 111.80(18) . . ? 
C9 C8 H8A 109.3 . . ? 
C4 C8 H8A 109.3 . . ? 
C9 C8 H8B 109.3 . . ? 
C4 C8 H8B 109.3 . . ? 
H8A C8 H8B 107.9 . . ? 
C10 C9 C8 112.2(2) . . ? 
C10 C9 H9A 109.2 . . ? 
C8 C9 H9A 109.2 . . ? 
C10 C9 H9B 109.2 . . ? 
C8 C9 H9B 109.2 . . ? 
H9A C9 H9B 107.9 . . ? 
C15 C10 C11 117.8(2) . . ? 
C15 C10 C9 121.1(2) . . ? 
C11 C10 C9 121.1(2) . . ? 
C12 C11 C10 121.1(2) . . ? 
C12 C11 H11 119.4 . . ? 
C10 C11 H11 119.4 . . ? 
C11 C12 C13 120.5(2) . . ? 
C11 C12 H12 119.8 . . ? 
C13 C12 H12 119.8 . . ? 
C14 C13 C12 119.1(2) . . ? 
C14 C13 H13 120.5 . . ? 
C12 C13 H13 120.5 . . ? 
C13 C14 C15 120.0(2) . . ? 
C13 C14 H14 120.0 . . ? 
C15 C14 H14 120.0 . . ? 
C14 C15 C10 121.5(2) . . ? 
C14 C15 H15 119.2 . . ? 
C10 C15 H15 119.2 . . ? 
C17 C16 C21 120.8(2) . . ? 
C17 C16 S1 118.99(17) . . ? 
C21 C16 S1 120.10(18) . . ? 
C16 C17 C18 119.3(2) . . ? 
C16 C17 H17 120.3 . . ? 
C18 C17 H17 120.3 . . ? 
C17 C18 C19 120.8(2) . . ? 
C17 C18 H18 119.6 . . ? 
C19 C18 H18 119.6 . . ? 
C20 C19 C18 118.4(2) . . ? 
C20 C19 C22 120.4(2) . . ? 
C18 C19 C22 121.2(2) . . ? 
C21 C20 C19 121.7(2) . . ? 
C21 C20 H20 119.2 . . ? 
C19 C20 H20 119.2 . . ? 
C19 C22 H22A 109.5 . . ? 
C19 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C19 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
C20 C21 C16 119.0(2) . . ? 
C20 C21 H21 120.5 . . ? 
C16 C21 H21 120.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              27.47 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.587 
_refine_diff_density_min   -0.522 
_refine_diff_density_rms    0.177 
