Synthesis of Functionalized Pyridazin-3(2H)-ones via Selective Bromine-Magnesium Exchange and Lactam Directed Ortho C-H Magnesiation
Tom Verhelst; Jens Maes; Zuming Liu; Sergey Sergeyev; Bert U. W. Maes; Journal of Organic Chemistry 76 (2011) 6670–6677; doi:10.1021/jo201009m

data_4026520
_publ_contact_author_address
;
Karel de Grote University College
Department of Applied Engineering
Salesianenlaan 30
B-2660 Antwerp
BELGIUM
;
_publ_contact_author_email       christophe.vandevelde@kdg.be
_publ_contact_author_name        'Christophe M.L. Vande Velde'
_publ_section_title
;
 Synthesis of Functionalized Pyridazin-3(2H)-ones via Selective
 Bromine-Magnesium Exchange and Lactam Directed Ortho C-H Magnesiation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6670
_journal_page_last               6677
_journal_paper_doi               10.1021/jo201009m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H11 Cl N2 O S'
_chemical_formula_sum            'C12 H11 Cl N2 O S'
_chemical_formula_weight         266.74
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   4.3122(12)
_cell_length_b                   10.505(3)
_cell_length_c                   27.486(7)
_cell_measurement_reflns_used    6882
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.44
_cell_volume                     1245.1(6)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker Saint v7.66A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker platform goniometer with Smart 1000'
_diffrn_measurement_method       \w-scans
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13935
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2008/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.1764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                3340
_reflns_number_total             3701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201009m_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4026520