Direct arylations of 2H-indazoles on water.
Ohnmacht, Stephan A.; Culshaw, Andrew J.; Greaney, Michael F.; Organic letters 12 (2010) 224–226; doi:10.1021/ol902537d

data_1503349
_publ_section_title
;
 Direct arylations of 2H-indazoles on water.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              224
_journal_page_last               226
_journal_paper_doi               10.1021/ol902537d
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'S Ohnmacht'
_chemical_formula_moiety         'C19 H13 Br N2'
_chemical_formula_sum            'C19 H13 Br N2'
_chemical_formula_weight         349.22
_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                 95.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7732(4)
_cell_length_b                   10.2447(3)
_cell_length_c                   14.0730(4)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.3295
_cell_measurement_theta_min      2.464
_cell_volume                     1544.71(9)
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Phi and Omega 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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14121
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_T_max  0.4845
_exptl_absorpt_correction_T_min  0.3791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'evaporation of DCM/hexane solution'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0474P)^2^+0.4209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                2709
_reflns_number_total             3156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902537d_si_002.cif
_cod_data_source_block           mg9006
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503349