Rapid access to 3-aminoindazoles from nitriles with hydrazines: a strategy to overcome the basicity barrier imparted by hydrazines.
Zhang, Chunyan; Zhao, Haowen; Li, Zehua; Liang, Zuyu; Qi, Shuo; Cai, Mingyu; Zhang, Sheng; Jia, Xiaofei; Zhang, Guoying; Hu, Mao-Lin; Chemical communications (Cambridge, England) 56 (2020) 9521–9524; doi:10.1039/d0cc03789c

data_7126865
_publ_section_title
;
 Rapid access to 3-aminoindazoles from nitriles with hydrazines: a
 strategy to overcome the basicity barrier imparted by hydrazines.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9521
_journal_page_last               9524
_journal_paper_doi               10.1039/d0cc03789c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C13 H10 Br N3'
_chemical_formula_sum            'C13 H10 Br N3'
_chemical_formula_weight         288.15
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.208(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7045(3)
_cell_length_b                   4.14060(10)
_cell_length_c                   20.5390(4)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.2470
_cell_measurement_theta_min      3.7330
_cell_volume                     1160.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -38.00  35.00   0.50    0.05    --   37.97 -57.00   0.00  146
  2  \w     44.00  69.00   0.50    0.05    --   37.97-129.00 132.00   50
  3  \w     86.00 120.00   0.50    0.06    --  112.45-129.00 132.00   68
  4  \w     39.00 106.00   0.50    0.06    --  112.45 -94.00 -30.00  134
  5  \w     92.00 123.00   0.50    0.06    --  112.45-140.00 -40.00   62
  6  \w     52.00  80.00   0.50    0.06    --  112.45 -94.00-180.00   56
  7  \w    145.00 173.00   0.50    0.06    --  112.45  45.00 -60.00   56
  8  \w    105.00 147.00   0.50    0.06    --  112.45 129.00-154.00   84
  9  \w     79.00 119.00   0.50    0.06    --  112.45  45.00 -60.00   80
 10  \w     29.00  55.00   0.50    0.06    --  112.45 -94.00  60.00   52
 11  \w   -103.00 -68.00   0.50    0.05    --  -37.97-129.00 132.00   70
 12  \w   -109.00 -65.00   0.50    0.05    --  -37.97 -57.00  30.00   88
 13  \w    -51.00  -9.00   0.50    0.05    --  -37.97 -57.00  30.00   84
 14  \w   -111.00 -61.00   0.50    0.05    --  -37.97-140.00 -40.00  100
 15  \w   -151.00 -60.00   0.50    0.06    --  -98.50-140.00 -40.00  182
 16  \w   -166.00 -84.00   0.50    0.06    --  -98.50-129.00 132.00  164
 17  \w   -168.00 -86.00   0.50    0.06    --  -98.50 -94.00  60.00  164
 18  \w   -172.00 -80.00   0.50    0.06    --  -98.50 -94.00-120.00  184
 19  \w    -81.00 -17.00   0.50    0.06    --  -98.50 111.00   0.00  128
 20  \w    -92.00 -29.00   0.50    0.05    --  -37.97 129.00-154.00  126
 21  \w    -82.00 -57.00   0.50    0.06    --  -98.50 129.00-154.00   50
;
_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      0.0199233000
_diffrn_orient_matrix_UB_12      0.3649538000
_diffrn_orient_matrix_UB_13      0.0075769000
_diffrn_orient_matrix_UB_21      0.1075633000
_diffrn_orient_matrix_UB_22      -0.0711000000
_diffrn_orient_matrix_UB_23      0.0241792000
_diffrn_orient_matrix_UB_31      0.0279443000
_diffrn_orient_matrix_UB_32      0.0145368000
_diffrn_orient_matrix_UB_33      -0.0709003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5424
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         3.727
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
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    1.649
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0728P)^2^+0.5134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             2051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03789c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7126865.cif.'
_cod_database_code               7126865
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'c h n Br'
_shelx_estimated_absorpt_t_max   0.456
_shelx_estimated_absorpt_t_min   0.456
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              79676
_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 4.269
_oxdiff_exptl_absorpt_empirical_full_min 0.536