Tandem thia-Fries rearrangement ‒ cyclisation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate benzyne precursors
Catherine Hall; Jaclyn L. Henderson; Guillaume Ernouf; Michael F. Greaney; Chem.Commun. 49 (2013) 7602–; doi:10.1039/c3cc44529a

data_7109650
_publ_section_title
;
 Tandem thia-Fries rearrangement -- cyclisation of
 2-(trimethylsilyl)phenyl trifluoromethanesulfonate benzyne precursors
;
_journal_name_full               Chem.Commun.
_journal_page_first              7602
_journal_paper_doi               10.1039/c3cc44529a
_journal_volume                  49
_journal_year                    2013
_chemical_compound_source        Henj471A
_chemical_formula_moiety         'C14 H10 Br2 O3 S1'
_chemical_formula_sum            'C14 H10 Br2 O3 S'
_chemical_formula_weight         418.11
_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
_audit_creation_date             07-02-13
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 98.312(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2297(2)
_cell_length_b                   15.8563(5)
_cell_length_c                   12.3339(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     1399.06(7)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16386
_diffrn_reflns_theta_full        27.003
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_min         2.106
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.946
_exptl_absorpt_correction_T_max  0.41
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.7565
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001527
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0700
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0700
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2934
_reflns_number_total             3430
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.3855(4)
_oxford_structure_analysis_title 'mg7002 in P2(1)/n'
_cod_data_source_file            c3cc44529a.txt
_cod_data_source_block           MG7002
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C14 H10 Br2 O3 S1'
_cod_database_code               7109650