Directed Regioselective ortho,ortho’-Magnesiations of Aromatics and Heterocycles using sBu2Mg in Toluene
Hess, Andreas; Prohaska, Jan Philip; Doerrich, Sabrina Bettina; Trauner, Florian; Lutter, Ferdinand Hermann; Lemaire, Sébastien; Wagschal, Simon; Karaghiosoff, Konstantin; Knochel, Paul; Chemical Science  (2021) –; doi:10.1039/D1SC01777B

data_1562680
_publ_section_title
;
 Directed Regioselective ortho,ortho&#x2019;-Magnesiations of Aromatics
 and Heterocycles using sBu2Mg in Toluene
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01777B
_journal_year                    2021
_chemical_formula_moiety         'C21 H24 Br N3 O5 Si'
_chemical_formula_sum            'C21 H24 Br N3 O5 Si'
_chemical_formula_weight         506.43
_chemical_name_systematic
;
(4-bromo-2,5-dimethoxyphenyl)(5-(4-(trimethylsilyl)-1H-
1,2,3-triazol-1-yl)benzo[d][1,3]dioxol-4-yl)methanol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                105.984(4)
_cell_angle_beta                 104.098(4)
_cell_angle_gamma                96.492(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0355(4)
_cell_length_b                   11.4221(6)
_cell_length_c                   13.0590(5)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.2820
_cell_measurement_theta_min      2.6860
_cell_volume                     1096.49(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.715
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.0145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01777b2.cif
_cod_data_source_block           test1
_cod_original_cell_volume        1096.48(9)
_cod_database_code               1562680
_shelx_estimated_absorpt_t_min   0.546
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2014-3
_shelx_res_checksum              87830
_shelx_hkl_checksum              14468