Synthesis of Bromo-, Boryl-, and Stannyl-Functionalized 1,2-Bis(trimethylsilyl)benzenes via Diels-Alder or C-H Activation Reactions
Christian Reus; Nai-Wei Liu; Michael Bolte; Hans-Wolfram Lerner; Matthias Wagner; Journal of Organic Chemistry 77 (2012) 3518–3523; doi:10.1021/jo3002936

data_4027135
_publ_section_title
;
 Synthesis of Bromo-, Boryl-, and Stannyl-Functionalized
 1,2-Bis(trimethylsilyl)benzenes via Diels-Alder or C-H Activation
 Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3518
_journal_page_last               3523
_journal_paper_doi               10.1021/jo3002936
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C5 H3 Br O2'
_chemical_formula_sum            'C5 H3 Br O2'
_chemical_formula_weight         174.98
_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                 97.688(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0278(6)
_cell_length_b                   6.1571(5)
_cell_length_c                   11.2580(7)
_cell_measurement_reflns_used    8723
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.5
_cell_volume                     551.46(7)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5222
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         3.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.344
_exptl_absorpt_correction_T_max  0.4055
_exptl_absorpt_correction_T_min  0.3077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0216
_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^)+(0.0287P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0496
_reflns_number_gt                917
_reflns_number_total             1036
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3002936_si_002_1.cif
_cod_data_source_block           wa1187
_cod_database_code               4027135