Preparation of polyfunctional indazoles and heteroarylazo compounds using highly functionalized zinc reagents.
Haag, Benjamin; Peng, Zhihua; Knochel, Paul; Organic letters 11 (2009) 4270–4273; doi:10.1021/ol901585k

data_1504123
_publ_section_title
;
 Preparation of polyfunctional indazoles and heteroarylazo compounds using
 highly functionalized zinc reagents.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4270
_journal_page_last               4273
_journal_paper_doi               10.1021/ol901585k
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C21 H12 N2 O'
_chemical_formula_weight         308.33
_space_group_IT_number           33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   15.8840(9)
_cell_length_b                   4.6260(2)
_cell_length_c                   19.4181(10)
_cell_measurement_temperature    200(2)
_cell_volume                     1426.83(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7787
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.319
_refine_ls_shift/su_mean         0.091
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                862
_reflns_number_total             1170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901585k_si_002.cif
_cod_data_source_block           mn324
_cod_database_code               1504123