One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based on regioselective [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes
Hussain, Ibrar; Riahi, Abdolmajid; Yawer, Mirza Arfan; Villinger, Alexander; Fischer, Christine; Görls, Helmar; Langer, Peter; Organic & Biomolecular Chemistry 6 (2008) 3542–3551; doi:10.1039/b803472a

data_7150930
_publ_section_title
;
 One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based
 on regioselective [3 + 3] cyclocondensations of
 1,3-bis(trimethylsilyloxy)-1,3-butadienes
;
_journal_issue                   19
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3542
_journal_page_last               3551
_journal_paper_doi               10.1039/b803472a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C14 H14 O3 S'
_chemical_formula_weight         262.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.843(4)
_cell_angle_beta                 105.477(5)
_cell_angle_gamma                98.661(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0866(5)
_cell_length_b                   9.2066(7)
_cell_length_c                   10.2121(9)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.04
_cell_volume                     627.70(9)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4319
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1008P)^2^+1.4708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2341
_reflns_number_gt                1645
_reflns_number_total             2743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803472a.txt
_cod_data_source_block           FO3241
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'NONE' changed to 'none' 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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150930