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_1562679
_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_absolute_configuration unk
_chemical_formula_moiety         'C9 H6 Cl2 I N3 S'
_chemical_formula_sum            'C9 H6 Cl2 I N3 S'
_chemical_formula_weight         386.03
_chemical_name_systematic
;
2-(3,5-dichloro-2-iodo-6-(methylthio)phenyl)-2H-1,2,3-triazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.5021(13)
_cell_length_b                   9.0794(3)
_cell_length_c                   9.4820(4)
_cell_measurement_reflns_used    5777
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.8740
_cell_measurement_theta_min      2.3180
_cell_volume                     2539.86(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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 0.986
_diffrn_measured_fraction_theta_max 0.987
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15592
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.347
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.370
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+5.4896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2254
_reflns_number_total             2462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01777b2.cif
_cod_data_source_block           test2
_cod_database_code               1562679
_shelx_estimated_absorpt_t_min   0.372
_shelx_estimated_absorpt_t_max   0.861
_shelxl_version_number           2014-3
_shelx_res_checksum              71803
_shelx_hkl_checksum              44872