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_7150929
_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            'C13 H9 F3 O3 S'
_chemical_formula_weight         302.26
_chemical_name_common
'Methyl 4-(thien-2-yl)-6-trifluormethyl-salicylate'
_chemical_name_systematic
;
Methyl 4-(thien-2-yl)-6-trifluormethyl-salicylate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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            8
_cell_length_a                   13.840(3)
_cell_length_b                   4.9310(10)
_cell_length_c                   35.860(7)
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      44.283
_cell_measurement_theta_min      5.978
_cell_volume                     2447.3(9)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            7225
_diffrn_reflns_theta_full        22.43
_diffrn_reflns_theta_max         22.43
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.7696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0478P)^2^+2.9174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2510
_reflns_number_total             2910
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803472a.txt
_cod_data_source_block           av_y214c1
_cod_original_sg_symbol_H-M      'P n a 2 1'
_cod_database_code               7150929