Readily prepared 3-chloro-1-(phenylthio)propene, a versatile three-carbon annulating agent.
Liu, Taoping; Zhao, Xiaoming; Lu, Long; Cohen, Theodore; Organic letters 11 (2009) 4576–4579; doi:10.1021/ol901818j

data_1504171
_publ_section_title
;
 Readily prepared 3-chloro-1-(phenylthio)propene, a versatile three-carbon
 annulating agent.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4576
_journal_page_last               4579
_journal_paper_doi               10.1021/ol901818j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C18 H24 O S'
_chemical_formula_weight         288.43
_space_group_IT_number           61
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_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   9.2519(9)
_cell_length_b                   16.7091(16)
_cell_length_c                   20.816(2)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.328
_cell_measurement_theta_min      4.876
_cell_volume                     3218.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
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_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00019(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.0820
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_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                1950
_reflns_number_total             3512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901818j_si_002.cif
_cod_data_source_block           Compound_21
_cod_depositor_comments
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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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3217.9(5)
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               1504171