Synthesis of fused indazole ring systems and application to nigeglanine hydrobromide.
Sather, Aaron C.; Berryman, Orion B.; Rebek, Jr, Julius; Organic letters 14 (2012) 1600–1603; doi:10.1021/ol300303s

data_1507180
_publ_section_title
;
 Synthesis of fused indazole ring systems and application to nigeglanine
 hydrobromide.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1600
_journal_page_last               1603
_journal_paper_doi               10.1021/ol300303s
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C9 H10 Br2 N2 O2'
_chemical_formula_sum            'C9 H10 Br2 N2 O2'
_chemical_formula_weight         338.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6859(4)
_cell_length_b                   15.6593(10)
_cell_length_c                   10.8980(7)
_cell_measurement_reflns_used    7136
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.7215
_cell_measurement_theta_min      6.9868
_cell_volume                     1130.04(12)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8634
_diffrn_reflns_theta_full        67.14
_diffrn_reflns_theta_max         67.14
_diffrn_reflns_theta_min         6.99
_diffrn_source
'Incoatec ImuS micro-focus source with MX mirrors'
_exptl_absorpt_coefficient_mu    8.980
_exptl_absorpt_correction_T_max  0.47
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular bar'
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.720
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.3332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                1940
_reflns_number_total             1985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300303s_si_003.cif
_cod_data_source_block           I
_cod_database_code               1507180