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_1507182
_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         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.2268
_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                 98.206(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5423(7)
_cell_length_b                   16.3967(15)
_cell_length_c                   8.2715(7)
_cell_measurement_reflns_used    4432
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      64.4139
_cell_measurement_theta_min      6.5153
_cell_volume                     1012.45(16)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7270
_diffrn_reflns_theta_full        65.10
_diffrn_reflns_theta_max         65.10
_diffrn_reflns_theta_min         6.52
_diffrn_source
'Incoatec ImuS micro-focus source with MX mirrors'
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.287
_refine_ls_extinction_coef       0.000929
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2270
_refine_ls_wR_factor_ref         0.2362
_reflns_number_gt                1590
_reflns_number_total             1704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300303s_si_005.cif
_cod_data_source_block           I
_cod_database_code               1507182