 
data_shelx
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C13 H13 Cl N2 O S' 
_chemical_formula_sum
 'C13 H13 Cl N2 O S' 
_chemical_formula_weight          280.76

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    24.9132(13)
_cell_length_b                    10.5411(5)
_cell_length_c                    10.4984(4)
_cell_angle_alpha                 90
_cell_angle_beta                  101.545(5)
_cell_angle_gamma                 90
_cell_volume                      2701.2(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     5953 
_cell_measurement_theta_min     2.7890
_cell_measurement_theta_max     27.3560
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.381          
_exptl_crystal_F_000              1168
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.35
_exptl_crystal_size_min           0.28
_exptl_absorpt_coefficient_mu     0.426
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.85027 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
; 
_oxdiff_exptl_absorpt_empirical_full_min           0.896
_oxdiff_exptl_absorpt_empirical_full_max           1.105
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
; 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source 'fine-focus sealed X-ray tube'   
_diffrn_source_type 'Enhance (Mo) X-ray Source'                   
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini'
_diffrn_detector 'CCD plate'
_diffrn_detector_type Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number             6994
_diffrn_reflns_av_unetI/netI      0.0401
_diffrn_reflns_v_R_equivalents    ?
_diffrn_reflns_limit_h_min        -33
_diffrn_reflns_limit_h_max        33
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.553
_diffrn_reflns_theta_max          29.135
_diffrn_reflns_theta_full         26.000
_diffrn_measured_fraction_theta_max   0.909
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.909
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.909
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              6994
_reflns_number_gt                 5554
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction      'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution     'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0834P)²+6.7424P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          6994
_refine_ls_number_parameters      325
_refine_ls_number_restraints      5
_refine_ls_R_factor_all           0.1037
_refine_ls_R_factor_gt            0.0854
_refine_ls_wR_factor_ref          0.2210
_refine_ls_wR_factor_gt           0.2111
_refine_ls_goodness_of_fit_ref    1.084
_refine_ls_restrained_S_all       1.090
_refine_ls_shift/su_max           0.011
_refine_ls_shift/su_mean          0.002
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1A Cl 0.36220(7) 0.54666(15) 0.66566(16) 0.0556(4) Uani 1 1 d . . . . .
Cl1B Cl 0.15031(8) 0.42904(17) 0.32186(19) 0.0668(5) Uani 1 1 d . . . . .
S1A S 0.47838(7) 1.13901(16) 0.83602(15) 0.0515(4) Uani 1 1 d . . . . .
S1B S 0.01598(8) -0.14724(18) 0.35435(18) 0.0637(5) Uani 1 1 d . . . . .
O1A O 0.45254(18) 0.8820(4) 0.4499(3) 0.0488(11) Uani 1 1 d . . . . .
O1B O 0.05098(18) 0.1121(4) -0.0010(4) 0.0509(10) Uani 1 1 d . . . . .
N1A N 0.46526(18) 0.9777(5) 0.6440(4) 0.0375(10) Uani 1 1 d . . . . .
H1A H 0.4956 1.0108 0.6335 0.045 Uiso 1 1 calc R U . . .
N1B N 0.03456(18) 0.0140(5) 0.1774(4) 0.0401(11) Uani 1 1 d . . . . .
H1B H 0.0040 -0.0160 0.1354 0.048 Uiso 1 1 calc R U . . .
N2A N 0.41051(18) 0.9405(4) 0.8007(4) 0.0336(9) Uani 1 1 d . . . . .
N2B N 0.08756(19) 0.0428(5) 0.3879(4) 0.0400(11) Uani 1 1 d . . . . .
C1A C 0.4457(2) 1.0042(5) 0.7577(4) 0.0317(11) Uani 1 1 d . . . . .
C1B C 0.0517(2) -0.0155(5) 0.3089(5) 0.0367(12) Uani 1 1 d . . . . .
C2A C 0.4371(2) 0.9012(5) 0.5508(4) 0.0364(12) Uani 1 1 d . . . . .
C2B C 0.0650(2) 0.0887(6) 0.1145(5) 0.0403(13) Uani 1 1 d . . . . .
C3A C 0.3854(2) 0.8476(6) 0.5808(4) 0.0409(13) Uani 1 1 d . . . . .
H3A1 H 0.3767 0.7681 0.5347 0.049 Uiso 1 1 calc R U . . .
H3A2 H 0.3554 0.9061 0.5519 0.049 Uiso 1 1 calc R U . . .
C3B C 0.1174(2) 0.1348(6) 0.1977(5) 0.0403(13) Uani 1 1 d . . . . .
H3B1 H 0.1282 0.2138 0.1627 0.048 Uiso 1 1 calc R U . . .
H3B2 H 0.1462 0.0730 0.1964 0.048 Uiso 1 1 calc R U . . .
C4A C 0.39230(19) 0.8251(5) 0.7276(4) 0.0288(10) Uani 1 1 d . . . . .
H4A H 0.4208 0.7605 0.7526 0.035 Uiso 1 1 calc R U . . .
C4B C 0.1106(2) 0.1554(5) 0.3371(5) 0.0337(11) Uani 1 1 d . . . . .
H4B H 0.0849 0.2258 0.3374 0.040 Uiso 1 1 calc R U . . .
C5A C 0.33973(19) 0.7750(5) 0.7621(4) 0.0273(10) Uani 1 1 d . . . . .
C5B C 0.1644(2) 0.1914(5) 0.4239(5) 0.0360(12) Uani 1 1 d . . . . .
C6A C 0.3230(2) 0.6510(5) 0.7370(5) 0.0353(11) Uani 1 1 d . . . . .
C6B C 0.1856(2) 0.3138(6) 0.4235(5) 0.0451(14) Uani 1 1 d . . . . .
C7A C 0.2768(3) 0.6028(6) 0.7717(6) 0.0478(14) Uani 1 1 d . . . . .
H7A H 0.2672 0.5183 0.7552 0.057 Uiso 1 1 calc R U . . .
C7B C 0.2345(3) 0.3457(8) 0.5040(6) 0.0608(19) Uani 1 1 d . . . . .
H7B H 0.2484 0.4273 0.5019 0.073 Uiso 1 1 calc R U . . .
C8A C 0.2446(3) 0.6811(7) 0.8316(7) 0.0630(19) Uani 1 1 d . . . . .
H8A H 0.2134 0.6496 0.8567 0.076 Uiso 1 1 calc R U . . .
C8B C 0.2619(3) 0.2596(9) 0.5849(8) 0.075(2) Uani 1 1 d . . . . .
H8B H 0.2949 0.2819 0.6390 0.090 Uiso 1 1 calc R U . . .
C9A C 0.2594(3) 0.8056(7) 0.8531(7) 0.0599(18) Uani 1 1 d . . . . .
H9A H 0.2375 0.8595 0.8908 0.072 Uiso 1 1 calc R U . . .
C9B C 0.2423(3) 0.1393(8) 0.5894(8) 0.068(2) Uani 1 1 d . . . . .
H9B H 0.2618 0.0801 0.6462 0.082 Uiso 1 1 calc R U . . .
C10A C 0.3067(2) 0.8523(6) 0.8196(5) 0.0398(12) Uani 1 1 d . . . . .
H10A H 0.3163 0.9368 0.8360 0.048 Uiso 1 1 calc R U . . .
C10B C 0.1933(2) 0.1056(7) 0.5094(6) 0.0530(15) Uani 1 1 d . . . . .
H10B H 0.1798 0.0238 0.5135 0.064 Uiso 1 1 calc R U . . .
C11A C 0.4479(3) 1.1473(7) 0.9788(6) 0.0539(16) Uani 1 1 d . . . . .
H11A H 0.4413 1.0609 1.0035 0.065 Uiso 1 1 calc R U . . .
H11B H 0.4753 1.1828 1.0486 0.065 Uiso 1 1 calc R U . . .
C11B C 0.0467(3) -0.1604(8) 0.5241(7) 0.068(2) Uani 1 1 d D . . . .
H11C H 0.0470 -0.0751 0.5591 0.082 Uiso 1 1 calc R U . A 1
H11D H 0.0209 -0.2083 0.5632 0.082 Uiso 1 1 calc R U . A 1
C12B C 0.1011(5) -0.2141(13) 0.5781(14) 0.058(4) Uiso 0.535(18) 1 d D U P B 1
H12B H 0.1195 -0.1950 0.6621 0.070 Uiso 0.535(18) 1 calc R U P B 1
C13B C 0.1229(8) -0.2907(15) 0.5019(16) 0.080(5) Uiso 0.535(18) 1 d D . P B 1
H13A H 0.1039 -0.3085 0.4182 0.096 Uiso 0.535(18) 1 calc R U P B 1
H13B H 0.1572 -0.3266 0.5321 0.096 Uiso 0.535(18) 1 calc R U P B 1
C22B C 0.0909(6) -0.259(2) 0.5173(18) 0.068(5) Uiso 0.465(18) 1 d D U P B 2
H22B H 0.0796 -0.3328 0.4704 0.082 Uiso 0.465(18) 1 calc R U P B 2
C23B C 0.1440(7) -0.251(3) 0.572(2) 0.104(8) Uiso 0.465(18) 1 d D . P B 2
H23A H 0.1573 -0.1795 0.6195 0.124 Uiso 0.465(18) 1 calc R U P B 2
H23B H 0.1677 -0.3168 0.5617 0.124 Uiso 0.465(18) 1 calc R U P B 2
C12A C 0.4013(5) 1.2126(10) 0.9748(12) 0.110(4) Uani 1 1 d D . . . .
H12A H 0.3861 1.1934 1.0465 0.133 Uiso 1 1 calc R U . . .
C13A C 0.3716(5) 1.2935(15) 0.9014(14) 0.142(5) Uani 1 1 d D . . . .
H13C H 0.3819 1.3215 0.8258 0.170 Uiso 1 1 calc R U . . .
H13D H 0.3398 1.3243 0.9237 0.170 Uiso 1 1 calc R U . . .
 
 
_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
Cl1A C6A 1.736(5) . ?
Cl1B C6B 1.735(7) . ?
S1A C1A 1.757(5) . ?
S1A C11A 1.812(6) . ?
S1B C1B 1.766(5) . ?
S1B C11B 1.799(7) . ?
O1A C2A 1.214(6) . ?
O1B C2B 1.219(7) . ?
N1A C2A 1.351(7) . ?
N1A C1A 1.404(6) . ?
N1B C2B 1.352(7) . ?
N1B C1B 1.396(7) . ?
N2A C1A 1.258(6) . ?
N2A C4A 1.461(7) . ?
N2B C1B 1.252(7) . ?
N2B C4B 1.464(7) . ?
C2A C3A 1.497(7) . ?
C2B C3B 1.500(8) . ?
C3A C4A 1.534(6) . ?
C3B C4B 1.523(7) . ?
C4A C5A 1.522(6) . ?
C4B C5B 1.511(7) . ?
C5A C10A 1.379(7) . ?
C5A C6A 1.380(7) . ?
C5B C10B 1.373(9) . ?
C5B C6B 1.394(8) . ?
C6A C7A 1.374(8) . ?
C6B C7B 1.379(9) . ?
C7A C8A 1.386(9) . ?
C7B C8B 1.334(11) . ?
C8A C9A 1.370(10) . ?
C8B C9B 1.362(12) . ?
C9A C10A 1.386(8) . ?
C9B C10B 1.382(9) . ?
C11A C12A 1.343(12) . ?
C11B C12B 1.475(13) . ?
C11B C22B 1.53(2) . ?
C12B C13B 1.327(9) . ?
C22B C23B 1.334(10) . ?
C12A C13A 1.281(9) . ?
 
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
C1A S1A C11A 101.2(3) . . ?
C1B S1B C11B 101.0(3) . . ?
C2A N1A C1A 121.1(4) . . ?
C2B N1B C1B 121.5(4) . . ?
C1A N2A C4A 114.9(4) . . ?
C1B N2B C4B 115.9(4) . . ?
N2A C1A N1A 125.7(5) . . ?
N2A C1A S1A 123.7(4) . . ?
N1A C1A S1A 110.6(4) . . ?
N2B C1B N1B 125.6(5) . . ?
N2B C1B S1B 122.6(4) . . ?
N1B C1B S1B 111.8(4) . . ?
O1A C2A N1A 121.5(5) . . ?
O1A C2A C3A 123.8(5) . . ?
N1A C2A C3A 114.7(4) . . ?
O1B C2B N1B 121.8(5) . . ?
O1B C2B C3B 123.8(5) . . ?
N1B C2B C3B 114.4(5) . . ?
C2A C3A C4A 110.0(4) . . ?
C2B C3B C4B 110.7(4) . . ?
N2A C4A C5A 110.8(4) . . ?
N2A C4A C3A 111.1(4) . . ?
C5A C4A C3A 111.3(4) . . ?
N2B C4B C5B 110.4(4) . . ?
N2B C4B C3B 111.2(4) . . ?
C5B C4B C3B 111.0(4) . . ?
C10A C5A C6A 117.4(5) . . ?
C10A C5A C4A 121.0(5) . . ?
C6A C5A C4A 121.6(4) . . ?
C10B C5B C6B 117.6(5) . . ?
C10B C5B C4B 121.0(5) . . ?
C6B C5B C4B 121.4(5) . . ?
C7A C6A C5A 122.4(5) . . ?
C7A C6A Cl1A 117.0(5) . . ?
C5A C6A Cl1A 120.6(4) . . ?
C7B C6B C5B 120.8(6) . . ?
C7B C6B Cl1B 118.9(5) . . ?
C5B C6B Cl1B 120.3(4) . . ?
C6A C7A C8A 119.5(6) . . ?
C8B C7B C6B 120.1(7) . . ?
C9A C8A C7A 118.9(6) . . ?
C7B C8B C9B 120.9(7) . . ?
C8A C9A C10A 120.9(6) . . ?
C8B C9B C10B 119.8(8) . . ?
C5A C10A C9A 120.9(6) . . ?
C5B C10B C9B 120.8(7) . . ?
C12A C11A S1A 120.1(7) . . ?
C12B C11B S1B 125.9(7) . . ?
C22B C11B S1B 100.0(8) . . ?
C13B C12B C11B 117.2(15) . . ?
C23B C22B C11B 127(2) . . ?
C13A C12A C11A 138.7(11) . . ?
 
_refine_diff_density_max    0.431
_refine_diff_density_min   -0.336
_refine_diff_density_rms    0.078

_shelxl_version_number 2014/6



