The N—O bond as an element of chirality: (<i>P</i>)-4-(<i>p</i>-chlorophenyl)-3-{2-[4-(<i>p</i>-toluenesulfonyl)piperazino]ethoxy}thiazole-2(3<i>H</i>)-thione
Hartung, Jens; Špehar, Kristina; Svoboda, Ingrid; Fuess, Hartmut; Acta Crystallographica Section E 59 (2003) o1894–o1895; doi:10.1107/S1600536803024814

data_2202650
_publ_section_title
;The N---O bond as an element of chirality:
 (<i>P</i>)-4-(<i>p</i>-chlorophenyl)-3-{2-[4-(<i>p</i>-toluenesulfonyl)piperazino]ethoxy}thiazole-2(3<i>H</i>)-thione
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1894
_journal_page_last               o1895
_journal_paper_doi               10.1107/S1600536803024814
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C22 H24 Cl N3 O3 S3'
_chemical_formula_moiety         'C22 H24 Cl N3 O3 S3'
_chemical_formula_sum            'C22 H24 Cl N3 O3 S3'
_chemical_formula_weight         510.07
_chemical_name_systematic
;
(P)-4-(p-chlorophenyl)-3-{2-[4-(p-
toluenesulfonyl)piperazino]ethoxy}thiazole-2(3H)-thione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2270(10)
_cell_length_b                   14.0980(10)
_cell_length_c                   22.1780(10)
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      16.85
_cell_measurement_theta_min      3.15
_cell_volume                     2572.3(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2002)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2002)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2002). PLATON2002 (Spek, 2002)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 'Sapphire CCD detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method
;
Rotation method data acquisition using \w
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17136
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.23
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.213
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0578P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                3163
_reflns_number_total             5188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fl6063.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Orthorhombic' changed to 'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202650
_cod_database_fobs_code          2202650