Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive Cyclization and Alkyne Insertion.
Wu, Tz-Yi; Dhole, Sandip; Selvaraju, Manikandan; Sun, Chung-Ming; ACS combinatorial science 20 (2018) 156–163; doi:10.1021/acscombsci.7b00170

data_4515840
_publ_section_title
;
 Regioselective Synthesis of Pyranone-Fused Indazoles via Reductive
 Cyclization and Alkyne Insertion.
;
_journal_issue                   3
_journal_name_full               'ACS combinatorial science'
_journal_page_first              156
_journal_page_last               163
_journal_paper_doi               10.1021/acscombsci.7b00170
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C30 H22 N2 O3'
_chemical_formula_weight         458.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.643(7)
_cell_angle_beta                 83.233(7)
_cell_angle_gamma                77.531(7)
_cell_formula_units_Z            4
_cell_length_a                   11.032(4)
_cell_length_b                   14.107(5)
_cell_length_c                   15.819(6)
_cell_measurement_reflns_used    2451
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.3361
_cell_measurement_theta_min      2.2411
_cell_volume                     2323.4(15)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_sigmaI/netI    0.1186
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34217
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.7467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         9338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2073
_refine_ls_R_factor_gt           0.0913
_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^)+(0.1522P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2968
_reflns_number_gt                3872
_reflns_number_total             9338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            co7b00170_si_004.cif
_cod_data_source_block           mo_120338_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2323.3(15)
_cod_database_code               4515840