Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium Exchange on Bromopyridazin-3(2H)-ones
Oxana Ryabtsova; Tom Verhelst; Mattijs Baeten; Christophe M. L. Vande Velde; Bert U. W. Maes; Journal of Organic Chemistry 74 (2009) 9440–9445; doi:10.1021/jo9020985

data_4025114
_publ_contact_author             'Christophe M.L. Vande Velde'
_publ_contact_author_email       christophe.vandevelde@kdg.be
_publ_section_title
;
Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium
Exchange on Bromopyridazin-3(2H)-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9440
_journal_page_last               9445
_journal_paper_doi               10.1021/jo9020985
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C11 H9 Br N2 O'
_chemical_formula_sum            'C11 H9 Br N2 O'
_chemical_formula_weight         265.11
_chemical_name_systematic
;
 2-benzyl-5-bromopyridazin-3(2H)one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.994(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8704(16)
_cell_length_b                   5.8208(10)
_cell_length_c                   17.713(3)
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.78
_cell_measurement_theta_min      2.34
_cell_volume                     999.0(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2008)'
_computing_data_collection       'Bruker SAINT (Bruker, 2008)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997), Mercury (Bruno, 2002)
;
_computing_publication_material
;
WinGX (Farrugia, 1999), PLATON (Spek, 2008)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type
;
area detector diffractometer Bruker Smart APEX
;
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11491
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.04
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    4.086
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0217
_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^)+(0.0294P)^2^+0.4173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0607
_reflns_number_gt                2844
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9020985_si_004.cif
_cod_data_source_block           11b
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4025114