Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2<i>H</i>-indazoles with allyl alcohols.
Nipate, Dhananjay S.; Meena, Neha; Swami, Prakash N.; Rangan, Krishnan; Kumar, Anil; Chemical communications (Cambridge, England) 60 (2024) 344–347; doi:10.1039/d3cc04600a

data_7132412
_publ_section_title
;
 Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and
 2-aryl-2<i>H</i>-indazoles with allyl alcohols.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              344
_journal_page_last               347
_journal_paper_doi               10.1039/d3cc04600a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H10 N2 O'
_chemical_formula_sum            'C16 H10 N2 O'
_chemical_formula_weight         246.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-13 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                75.453(2)
_cell_angle_beta                 79.894(2)
_cell_angle_gamma                79.458(2)
_cell_formula_units_Z            4
_cell_length_a                   8.0807(2)
_cell_length_b                   11.4488(3)
_cell_length_c                   13.0502(4)
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      78.9640
_cell_measurement_theta_min      4.7020
_cell_volume                     1138.21(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -89.00 -37.00   0.50    2.16    --    0.00 -37.00 120.00  104
  2  \w     56.00  86.00   0.50    2.16    --    0.00  37.00  90.00   60
  3  \w    -17.00  44.00   0.50    2.16    --    0.00  37.00  90.00  122
  4  \w    -86.00  16.00   0.50    2.16    --    0.00 -37.00-150.00  204
  5  \w    -31.00  -5.00   0.50    2.16    --    0.00 -37.00 120.00   52
  6  \w    -24.00  29.00   0.50    2.16    --    0.00 -77.00  90.00  106
  7  \w     54.00 123.00   0.50    8.65    --  107.20 -30.00 -30.00  138
  8  \w    102.00 128.00   0.50    8.65    --  107.20  30.00 -60.00   52
  9  \w     18.00  44.00   0.50    8.65    --  107.20 -30.00 -30.00   52
 10  \w     90.00 131.00   0.50    8.65    --  107.20 -82.00 -60.00   82
 11  \w     39.00 102.00   0.50    8.65    --  107.20 -82.00-180.00  126
 12  \w    141.00 197.00   0.50    8.65    --  107.20  30.00 -60.00  112
 13  \w     39.00  75.00   0.50    8.65    --  107.20 -82.00 120.00   72
 14  \w     94.00 132.00   0.50    8.65    --  107.20 -82.00 120.00   76
 15  \w     22.00  56.00   0.50    8.65    --  107.20 -82.00 -60.00   68
 16  \w     92.00 117.00   0.50    8.65    --  107.20 -45.00  60.00   50
 17  \w     99.00 140.00   0.50    8.65    --  107.20 -82.00   0.00   82
 18  \w     43.00  81.00   0.50    8.65    --  107.20 -82.00   0.00   76
 19  \w     18.00  54.00   0.50    8.65    --  107.20 -61.00-120.00   72
 20  \w     65.00 109.00   0.50    8.65    --  107.20 -61.00-120.00   88
 21  \w     18.00 129.00   0.50    8.65    --  107.20 -15.00 -30.00  222
 22  \w     99.00 124.00   0.50    8.65    --  107.20  82.00-180.00   50
 23  \w     18.00 124.00   0.50    8.65    --  107.20 -82.00-120.00  212
 24  \w     60.00 137.00   0.50    8.65    --  107.20 -82.00  60.00  154
 25  \w     90.00 131.00   0.50    8.65    --  107.20  30.00 150.00   82
 26  \w     36.00 127.00   0.50    8.65    --  107.20 -82.00 -30.00  182
 27  \w     85.00 195.00   0.50    8.65    --  107.20  15.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0128590000
_diffrn_orient_matrix_UB_12      0.1181347000
_diffrn_orient_matrix_UB_13      -0.0872757000
_diffrn_orient_matrix_UB_21      0.0488834000
_diffrn_orient_matrix_UB_22      -0.0754650000
_diffrn_orient_matrix_UB_23      -0.0861383000
_diffrn_orient_matrix_UB_31      -0.1891032000
_diffrn_orient_matrix_UB_32      0.0097237000
_diffrn_orient_matrix_UB_33      -0.0108576000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.868
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0598P)^2^+0.2010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4215
_reflns_number_total             4788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04600a2.cif
_cod_data_source_block           exp_1263_ak_dsn-892_20221107
_cod_depositor_comments          'Adding full bibliography for 7132412.cif.'
_cod_database_code               7132412
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H10 N2 O'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C103(H103), C104(H104), C105(H105), C106(H106), C109(H109),
  C111(H111), C112(H112), C113(H113), C114(H114), C116(H116)
;
_shelx_res_checksum              57398
_shelx_hkl_checksum              11664
_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 1.855
_oxdiff_exptl_absorpt_empirical_full_min 0.663