 
data_2007src0763
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr F. H. Fry
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H28 Cl N O2 S'
_chemical_formula_weight          369.93
 
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    'P na2(1)'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'
 
_cell_length_a                    15.4076(3)
_cell_length_b                    12.9924(4)
_cell_length_c                    9.3800(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1877.70(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12291
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Rod
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.309
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              792
_exptl_absorpt_coefficient_mu     0.326
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6519
_exptl_absorpt_correction_T_max   0.7458
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
 SADABS was used to perform the Absorption correction and gives the 
estimated minimum and maximum transmission values as 0.6519 and 0.7458.
;
 
_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    '10cm confocal mirrors'
_diffrn_measurement_device_type    
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method         'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             10624
_diffrn_reflns_av_R_equivalents   0.0506
_diffrn_reflns_av_sigmaI/netI     0.0598
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          28.50
_reflns_number_total              4506
_reflns_number_gt                 4215
_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    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., 
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 
2004)
;
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON/PLUTON (Spek, A. L., 1998)'
_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.

The refined Flack parameter for this structure is 0.40 (12) using 1994, 79 % 
Friedel pairs. The inverted structure gives a Flack parameter of 0.59 (12). 
For this reason the structure has been refined as an inversion twin with the 
ratio of enantiomers being 0.40 (12).
;
 
_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)+(0.0627P)²+4.7927P] 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, 1994 Friedel pairs'
_refine_ls_abs_structure_Flack    0.40(12)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          4506
_refine_ls_number_parameters      220
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0743
_refine_ls_R_factor_gt            0.0699
_refine_ls_wR_factor_ref          0.1761
_refine_ls_wR_factor_gt           0.1726
_refine_ls_goodness_of_fit_ref    1.074
_refine_ls_restrained_S_all       1.074
_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 0.6588(3) 0.0084(3) 0.4155(7) 0.0303(9) Uani 1 1 d . . .
H1A H 0.6527 0.0078 0.3115 0.046 Uiso 1 1 calc R . .
H1B H 0.6657 -0.0623 0.4503 0.046 Uiso 1 1 calc R . .
H1C H 0.7099 0.0490 0.4420 0.046 Uiso 1 1 calc R . .
C2 C 0.5781(3) 0.0562(3) 0.4821(5) 0.0235(8) Uani 1 1 d . . .
H2 H 0.5813 0.0473 0.5878 0.028 Uiso 1 1 calc R . .
C3 C 0.5669(3) 0.1715(3) 0.4487(5) 0.0236(8) Uani 1 1 d . . .
H3 H 0.6174 0.2081 0.4925 0.028 Uiso 1 1 calc R . .
C4 C 0.4831(3) 0.2177(3) 0.5167(4) 0.0198(8) Uani 1 1 d . . .
H4 H 0.4516 0.1618 0.5683 0.024 Uiso 1 1 calc R . .
C5 C 0.4717(3) 0.2159(4) 0.2553(4) 0.0231(9) Uani 1 1 d . . .
H5A H 0.4457 0.1506 0.2216 0.028 Uiso 1 1 calc R . .
H5B H 0.4645 0.2689 0.1804 0.028 Uiso 1 1 calc R . .
C6 C 0.5647(3) 0.2017(4) 0.2915(5) 0.0317(10) Uani 1 1 d . . .
H6A H 0.5973 0.2664 0.2758 0.038 Uiso 1 1 calc R . .
H6B H 0.5907 0.1469 0.2320 0.038 Uiso 1 1 calc R . .
C7 C 0.4989(3) 0.3070(3) 0.6201(4) 0.0198(7) Uani 1 1 d . . .
H7 H 0.4406 0.3343 0.6476 0.024 Uiso 1 1 calc R . .
C8 C 0.5506(3) 0.3982(3) 0.5568(5) 0.0236(8) Uani 1 1 d . . .
H8A H 0.6093 0.3746 0.5289 0.028 Uiso 1 1 calc R . .
H8B H 0.5208 0.4238 0.4702 0.028 Uiso 1 1 calc R . .
C9 C 0.5584(3) 0.4854(3) 0.6652(5) 0.0277(9) Uani 1 1 d . . .
H9A H 0.5000 0.5125 0.6878 0.033 Uiso 1 1 calc R . .
H9B H 0.5932 0.5421 0.6239 0.033 Uiso 1 1 calc R . .
C10 C 0.6019(3) 0.4469(4) 0.8020(5) 0.0298(9) Uani 1 1 d . . .
H10A H 0.6623 0.4258 0.7804 0.036 Uiso 1 1 calc R . .
H10B H 0.6043 0.5037 0.8722 0.036 Uiso 1 1 calc R . .
C11 C 0.5533(3) 0.3563(4) 0.8666(5) 0.0328(10) Uani 1 1 d . . .
H11A H 0.4954 0.3793 0.8993 0.039 Uiso 1 1 calc R . .
H11B H 0.5856 0.3302 0.9505 0.039 Uiso 1 1 calc R . .
C12 C 0.5428(3) 0.2699(3) 0.7578(5) 0.0266(9) Uani 1 1 d . . .
H12A H 0.5076 0.2140 0.8004 0.032 Uiso 1 1 calc R . .
H12B H 0.6006 0.2413 0.7345 0.032 Uiso 1 1 calc R . .
C13 C 0.2898(2) 0.1193(2) 0.4013(5) 0.0174(6) Uani 1 1 d . . .
C14 C 0.2667(3) 0.0712(3) 0.2746(4) 0.0247(9) Uani 1 1 d . . .
H14 H 0.2678 0.1085 0.1875 0.030 Uiso 1 1 calc R . .
C15 C 0.2420(3) -0.0320(4) 0.2756(5) 0.0294(10) Uani 1 1 d . . .
H15 H 0.2265 -0.0649 0.1888 0.035 Uiso 1 1 calc R . .
C16 C 0.2397(2) -0.0866(2) 0.4018(5) 0.0209(7) Uani 1 1 d . . .
C17 C 0.2623(3) -0.0378(3) 0.5287(5) 0.0255(9) Uani 1 1 d . . .
H17 H 0.2607 -0.0749 0.6160 0.031 Uiso 1 1 calc R . .
C18 C 0.2872(3) 0.0648(3) 0.5280(5) 0.0228(9) Uani 1 1 d . . .
H18 H 0.3025 0.0979 0.6148 0.027 Uiso 1 1 calc R . .
C19 C 0.2134(3) -0.1985(3) 0.4030(6) 0.0285(8) Uani 1 1 d . . .
H19A H 0.1576 -0.2064 0.3539 0.043 Uiso 1 1 calc R . .
H19B H 0.2077 -0.2222 0.5017 0.043 Uiso 1 1 calc R . .
H19C H 0.2576 -0.2395 0.3540 0.043 Uiso 1 1 calc R . .
N1 N 0.43052(16) 0.2502(2) 0.3934(5) 0.0167(5) Uani 1 1 d . . .
O1 O 0.3012(2) 0.2914(2) 0.5357(3) 0.0232(6) Uani 1 1 d . . .
O2 O 0.2936(2) 0.2943(2) 0.2706(3) 0.0231(7) Uani 1 1 d . . .
S1 S 0.32487(5) 0.24788(6) 0.40037(14) 0.01646(18) Uani 1 1 d . . .
Cl1 Cl 0.48551(7) -0.01701(7) 0.41558(19) 0.0411(3) 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 C2 1.524(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.540(5) . ?
C2 Cl1 1.824(4) . ?
C2 H2 1.0000 . ?
C3 C6 1.526(7) . ?
C3 C4 1.560(6) . ?
C3 H3 1.0000 . ?
C4 N1 1.474(6) . ?
C4 C7 1.532(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.484(6) . ?
C5 N1 1.509(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.536(6) . ?
C7 C8 1.546(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.527(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.532(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.384(6) . ?
C13 C14 1.389(6) . ?
C13 S1 1.756(3) . ?
C14 C15 1.393(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(6) . ?
C16 C19 1.509(5) . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 S1 1.629(3) . ?
O1 S1 1.436(3) . ?
O2 S1 1.442(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.8(3) . . ?
C1 C2 Cl1 106.6(3) . . ?
C3 C2 Cl1 110.5(3) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
Cl1 C2 H2 108.6 . . ?
C6 C3 C2 116.7(4) . . ?
C6 C3 C4 106.1(3) . . ?
C2 C3 C4 112.6(3) . . ?
C6 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
N1 C4 C7 111.6(3) . . ?
N1 C4 C3 104.2(3) . . ?
C7 C4 C3 114.8(3) . . ?
N1 C4 H4 108.7 . . ?
C7 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C6 C5 N1 104.2(3) . . ?
C6 C5 H5A 110.9 . . ?
N1 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
N1 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C5 C6 C3 106.0(4) . . ?
C5 C6 H6A 110.5 . . ?
C3 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
C3 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?
C4 C7 C12 111.4(3) . . ?
C4 C7 C8 114.8(3) . . ?
C12 C7 C8 109.7(3) . . ?
C4 C7 H7 106.8 . . ?
C12 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C9 C8 C7 110.7(4) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 110.5(4) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.8(4) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 110.8(4) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C7 112.2(3) . . ?
C11 C12 H12A 109.2 . . ?
C7 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C7 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C18 C13 C14 119.9(3) . . ?
C18 C13 S1 119.9(3) . . ?
C14 C13 S1 120.2(3) . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 C19 120.5(4) . . ?
C17 C16 C19 120.0(4) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C13 C18 C17 120.2(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 N1 C5 110.9(3) . . ?
C4 N1 S1 120.9(3) . . ?
C5 N1 S1 116.7(3) . . ?
O1 S1 O2 119.83(15) . . ?
O1 S1 N1 106.3(2) . . ?
O2 S1 N1 107.0(2) . . ?
O1 S1 C13 107.0(2) . . ?
O2 S1 C13 107.4(2) . . ?
N1 S1 C13 108.96(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              28.50
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    1.193
_refine_diff_density_min   -0.769
_refine_diff_density_rms    0.096
