Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives
Chen, Yichun; Lu, Ziqi; He, Wenfen; Zhu, Huanyi; Lu, Weilong; Shi, Junjun; Sheng, Jie; Xie, Wucheng; RSC Advances 14 (2024) 4804–4809; doi:10.1039/D3RA07466H

data_7248101
_publ_section_title
;
 Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to
 synthesize unsubstituted 1-aminoindole derivatives
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              4804
_journal_page_last               4809
_journal_paper_doi               10.1039/D3RA07466H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C10 H10 N2 O'
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-15
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.356(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.4933(3)
_cell_length_b                   9.0418(3)
_cell_length_c                   21.8135(9)
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.0010
_cell_measurement_theta_min      4.1070
_cell_volume                     1835.74(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -19.00  64.00   1.00    1.00    --   40.73 -38.00  60.00   83
  2  \w     94.00 171.00   1.00    2.82    --  106.95  30.00 120.00   77
  3  \w    151.00 177.00   1.00    2.82    --  106.95 125.00  30.00   26
  4  \w     93.00 161.00   1.00    2.82    --  106.95  30.00-120.00   68
  5  \w     64.00 119.00   1.00    2.82    --  106.95-125.00-180.00   55
  6  \w     32.00 139.00   1.00    2.82    --  106.95 -77.00 -30.00  107
  7  \w     31.00  77.00   1.00    2.82    --  106.95 -30.00 120.00   46
  8  \w    -65.00  10.00   1.00    1.00    --  -40.73  57.00 -30.00   75
  9  \w   -108.00 -21.00   1.00    1.00    --  -40.73 -38.00-180.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1043407000
_diffrn_orient_matrix_UB_12      0.0168474000
_diffrn_orient_matrix_UB_13      0.0633899000
_diffrn_orient_matrix_UB_21      0.1271018000
_diffrn_orient_matrix_UB_22      -0.0383922000
_diffrn_orient_matrix_UB_23      -0.0314138000
_diffrn_orient_matrix_UB_31      0.0191294000
_diffrn_orient_matrix_UB_32      0.1649843000
_diffrn_orient_matrix_UB_33      -0.0138771000
_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  0.0185
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.295
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1793
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.6792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1574
_reflns_number_total             1793
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra07466h3.cif
_cod_data_source_block           23-2
_cod_database_code               7248101
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C3: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              45976
_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 1.780
_oxdiff_exptl_absorpt_empirical_full_min 0.609