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_4034192
_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         260.30
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.6080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2263(2)
_cell_length_b                   6.08740(10)
_cell_length_c                   16.4983(2)
_cell_measurement_reflns_used    8813
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8610
_cell_measurement_theta_min      3.6220
_cell_volume                     1226.64(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9839
_diffrn_measured_fraction_theta_max 0.9839
_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     44.00 115.00   0.50    0.05    --   48.66  38.00-120.00  142
  2  \w    149.00 177.00   0.50    0.15    --  105.75 125.00-180.00   56
  3  \w    120.00 145.00   0.50    0.15    --  105.75 138.00 -71.00   50
  4  \w    106.00 142.00   0.50    0.15    --  105.75 125.00-180.00   72
  5  \w     39.00  82.00   0.50    0.15    --  105.75 -30.00-180.00   86
  6  \w     58.00 109.00   0.50    0.15    --  105.75 -61.00-180.00  102
  7  \w     70.00  96.00   0.50    0.15    --  105.75 -95.00-120.00   52
  8  \w     39.00 102.00   0.50    0.05    --   48.66-138.00-133.00  126
  9  \w     39.00 127.00   0.50    0.15    --  105.75-138.00-133.00  176
 10  \w     35.00 122.00   0.50    0.15    --  105.75-132.00  42.00  174
 11  \w     44.00 116.00   0.50    0.15    --  105.75-125.00 150.00  144
 12  \w     36.00  82.00   0.50    0.15    --  105.75 -30.00  90.00   92
 13  \w     35.00 115.00   0.50    0.15    --  105.75-125.00  60.00  160
 14  \w     40.00  79.00   0.50    0.15    --  105.75 -45.00-120.00   78
 15  \w     38.00  63.00   0.50    0.15    --  105.75 -30.00-150.00   50
 16  \w     34.00 116.00   0.50    0.15    --  105.75-125.00-180.00  164
 17  \w     97.00 172.00   0.50    0.15    --  105.75 125.00 150.00  150
 18  \w    109.00 134.00   0.50    0.15    --  105.75 132.00 111.00   50
 19  \w    -55.00 -12.00   0.50    0.15    --  -84.25  30.00-180.00   86
 20  \w   -100.00 -17.00   0.50    0.05    --  -48.66 138.00 -71.00  166
 21  \w    -96.00 -14.00   0.50    0.15    --  -84.25 132.00 111.00  164
 22  \w   -101.00 -17.00   0.50    0.15    --  -84.25 138.00 -71.00  168
 23  \w   -119.00 -28.00   0.50    0.05    --  -48.66 -77.00  60.00  182
 24  \w   -119.00 -66.00   0.50    0.05    --  -48.66-132.00  42.00  106
 25  \w   -119.00 -70.00   0.50    0.05    --  -48.66-125.00  90.00   98
 26  \w   -119.00 -62.00   0.50    0.05    --  -48.66-138.00-133.00  114
;
_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      0.1217664000
_diffrn_orient_matrix_UB_12      0.0567175000
_diffrn_orient_matrix_UB_13      -0.0083976000
_diffrn_orient_matrix_UB_21      -0.0275914000
_diffrn_orient_matrix_UB_22      0.2465856000
_diffrn_orient_matrix_UB_23      0.0039398000
_diffrn_orient_matrix_UB_31      0.0179595000
_diffrn_orient_matrix_UB_32      -0.0052972000
_diffrn_orient_matrix_UB_33      0.0930085000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13422
_diffrn_reflns_theta_full        77.3839
_diffrn_reflns_theta_max         77.38
_diffrn_reflns_theta_min         3.62
_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  0.79439
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.4094
_exptl_crystal_description       block
_exptl_crystal_F_000             545.6745
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2044
_refine_diff_density_min         -0.2364
_refine_diff_density_rms         0.0548
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             12.2136
_refine_ls_goodness_of_fit_ref   1.0307
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.0303
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.4921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2346
_reflns_number_total             2571
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01021_si_002.cif
_cod_data_source_block           Mark2_4_6_2018_1
_cod_database_code               4034192
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H2-N2
 0.93 with sigma of 0.005
 H1-N1
 0.93 with sigma of 0.005
3. Others
 Fixed Sof: H1(0.82) H2(0.18)
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C3(H3), C14(H14), C16(H16), C15(H15), C6(H6), C4(H4),
 C5(H5)
;
_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 1.464
_oxdiff_exptl_absorpt_empirical_full_min 0.655