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_4027137
_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           33
_symmetry_cell_setting           orthorhombic
_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            4
_cell_length_a                   10.664(3)
_cell_length_b                   13.107(3)
_cell_length_c                   3.9339(9)
_cell_measurement_reflns_used    1508
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.7
_cell_volume                     549.9(2)
_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 0.975
_diffrn_measured_fraction_theta_max 0.976
_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  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1571
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.53
_diffrn_reflns_theta_min         3.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.365
_exptl_absorpt_correction_T_max  0.5570
_exptl_absorpt_correction_T_min  0.1662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.850
_refine_diff_density_rms         0.249
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.365
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         855
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.364
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0800
_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^)+(0.0825P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.1938
_reflns_number_gt                647
_reflns_number_total             855
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3002936_si_002_3.cif
_cod_data_source_block           wa1221
_cod_database_code               4027137