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_1504170
_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            'C16 H22 O S'
_chemical_formula_weight         262.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 108.452(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.777(4)
_cell_length_b                   6.552(2)
_cell_length_c                   16.810(5)
_cell_measurement_reflns_used    1337
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.658
_cell_measurement_theta_min      4.613
_cell_volume                     1439.4(7)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_sigmaI/netI    0.1174
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7675
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3115
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1554
_reflns_number_total             3115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901818j_si_002.cif
_cod_data_source_block           Compound_10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        1439.3(8)
_cod_original_sg_symbol_H-M      'P 2(1)/n'
_cod_database_code               1504170