Mild and efficient synthesis of (Z)-alpha-chloroalkylidene-beta-lactones via the PdCl2-catalyzed cyclocarbonylation of 2-alkynols.
Ma, Shengming; Wu, Bin; Zhao, Shimin; Organic letters 5 (2003) 4429–4432; doi:10.1021/ol0357245

data_1507395
_publ_section_title
;
 Mild and efficient synthesis of (Z)-alpha-chloroalkylidene-beta-lactones
 via the PdCl2-catalyzed cyclocarbonylation of 2-alkynols.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4429
_journal_page_last               4432
_journal_paper_doi               10.1021/ol0357245
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C13 H13 Cl O2'
_chemical_formula_weight         236.68
_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                 101.777(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8786(13)
_cell_length_b                   18.626(2)
_cell_length_c                   13.5620(17)
_cell_measurement_reflns_used    1865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.711
_cell_measurement_theta_min      4.374
_cell_volume                     2442.9(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 0.936
_diffrn_measured_fraction_theta_max 0.936
_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  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14691
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57282
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0402P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                2497
_reflns_number_total             5663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0357245si20030909_045751.cif
_cod_data_source_block           cd23166
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C13 H13 O2  Cl'
_cod_database_code               1507395