2<i>H</i>-Indazole Tautomers Stabilized by Intra- and Intermolecular Hydrogen Bonds.
Sigalov, Mark V.; Afonin, Andrey V.; Sterkhova, Irina V.; Shainyan, Bagrat A.; The Journal of organic chemistry 84 (2019) 9075–9086; doi:10.1021/acs.joc.9b01021

data_4034191
_publ_section_title
;
 2<i>H</i>-Indazole Tautomers Stabilized by Intra- and Intermolecular
 Hydrogen Bonds.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9075
_journal_page_last               9086
_journal_paper_doi               10.1021/acs.joc.9b01021
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.6120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2386(2)
_cell_length_b                   6.08660(10)
_cell_length_c                   16.4889(2)
_cell_measurement_reflns_used    8900
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      77.2840
_cell_measurement_theta_min      3.6220
_cell_volume                     1227.01(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -23.00  56.00   0.50    1.00    --   48.66 -34.00  39.00  158
  2  \w     34.00  81.00   0.50    2.00    --  105.75 -34.00  39.00   94
  3  \w     42.00  84.00   0.50    2.00    --  105.75 -45.00  90.00   84
  4  \w     34.00 127.00   0.50    2.00    --  105.75 -77.00  60.00  186
  5  \w     34.00 109.00   0.50    2.00    --  105.75 -95.00-120.00  150
  6  \w     84.00 109.00   0.50    2.00    --  105.75 -61.00-120.00   50
  7  \w     42.00 121.00   0.50    1.00    --   48.66  34.00-162.00  158
  8  \w     99.00 178.00   0.50    2.00    --  105.75  34.00-162.00  158
  9  \w    124.00 177.00   0.50    2.00    --  105.75  45.00 -90.00  106
 10  \w     45.00  75.00   0.50    2.00    --  105.75 -61.00-120.00   60
 11  \w     34.00 127.00   0.50    2.00    --  105.75 -77.00-180.00  186
 12  \w     34.00  82.00   0.50    2.00    --  105.75 -30.00-180.00   96
 13  \w     34.00  86.00   0.50    2.00    --  105.75 -45.00-120.00  104
 14  \w     31.00  94.00   0.50    1.00    --   48.66-125.00 -90.00  126
 15  \w     34.00  86.00   0.50    2.00    --  105.75 -45.00  30.00  104
 16  \w     34.00 116.00   0.50    2.00    --  105.75-125.00  60.00  164
 17  \w     34.00 110.00   0.50    2.00    --  105.75 -61.00 150.00  152
 18  \w     34.00  82.00   0.50    2.00    --  105.75 -30.00 -90.00   96
 19  \w    -56.00  23.00   0.50    1.00    --  -48.66  34.00-162.00  158
 20  \w    -63.00 -12.00   0.50    2.00    --  -84.25  34.00-162.00  102
 21  \w   -120.00 -41.00   0.50    1.00    --  -48.66 -34.00  39.00  158
 22  \w   -119.00 -70.00   0.50    1.00    --  -48.66-125.00 -30.00   98
 23  \w   -119.00 -70.00   0.50    1.00    --  -48.66-125.00-150.00   98
 24  \w   -156.00 -77.00   0.50    2.00    --  -84.25 -34.00  39.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1092877000
_diffrn_orient_matrix_UB_12      0.0520477000
_diffrn_orient_matrix_UB_13      0.0460683000
_diffrn_orient_matrix_UB_21      0.0626746000
_diffrn_orient_matrix_UB_22      -0.0984975000
_diffrn_orient_matrix_UB_23      -0.0703095000
_diffrn_orient_matrix_UB_31      0.0021484000
_diffrn_orient_matrix_UB_32      0.2273170000
_diffrn_orient_matrix_UB_33      -0.0409893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.713
_diffrn_reflns_theta_min         3.615
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.5908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2344
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01021_si_003.cif
_cod_data_source_block           mark_4_6_2018_3
_cod_database_code               4034191
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C13(H13), C16(H16), C3(H3), C15(H15), C6(H6), C14(H14),
 C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.007
_oxdiff_exptl_absorpt_empirical_full_min 0.681