Synthesis of indoles and carbazoles from a lignin model compound α-hydroxyacetophenone
Chen, Zhiyan; Huang, Wenbo; Yi, Liqi; Dong, Xiaohan; Sheng, Keyan; Li, Minghao; Bai, Rongxian; Sidorenko, A. Yu.; Huang, Jiang; Gu, Yanlong; Green Chemistry 24 (2022) 2919–2926; doi:10.1039/D1GC04892A

data_7244591
_publ_section_title
;
 Synthesis of indoles and carbazoles from a lignin model compound
 \a-hydroxyacetophenone
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2919
_journal_page_last               2926
_journal_paper_doi               10.1039/D1GC04892A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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             2021-12-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                92.730(5)
_cell_angle_beta                 90.852(5)
_cell_angle_gamma                108.525(7)
_cell_formula_units_Z            4
_cell_length_a                   7.9813(6)
_cell_length_b                   11.4019(10)
_cell_length_c                   17.8408(8)
_cell_measurement_reflns_used    5706
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2870
_cell_measurement_theta_min      2.4300
_cell_volume                     1536.9(2)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.966
_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    -52.00  18.00   1.00    1.00    --  -40.98  38.00  90.00   70
  2  \w    -85.00  41.00   1.00    1.00    --  -40.98   0.00  30.00  126
  3  \w     29.00  95.00   1.00    1.00    --   40.98-125.00   0.00   66
  4  \w     36.00 118.00   1.00    1.00    --  106.95 -61.00   0.00   82
  5  \w     75.00 121.00   1.00    1.00    --  106.95-125.00 -60.00   46
  6  \w     75.00 108.00   1.00    1.00    --  106.95 -94.00 -30.00   33
  7  \w     42.00 134.00   1.00    1.00    --  106.95 -61.00-120.00   92
  8  \w     88.00 152.00   1.00    1.00    --  106.95  30.00 -30.00   64
  9  \w     84.00 166.00   1.00    1.00    --  106.95  45.00 -90.00   82
 10  \w    106.00 131.00   1.00    1.00    --  106.95 125.00  90.00   25
 11  \w     31.00 137.00   1.00    1.00    --  106.95 -15.00 -60.00  106
 12  \w     84.00 118.00   1.00    1.00    --  106.95-125.00 120.00   34
 13  \w     52.00  78.00   1.00    1.00    --  106.95-125.00 120.00   26
 14  \w     41.00  67.00   1.00    1.00    --  106.95-125.00 150.00   26
 15  \w     35.00 140.00   1.00    1.00    --  106.95 -77.00 120.00  105
 16  \w     32.00 135.00   1.00    1.00    --  106.95 -30.00  90.00  103
 17  \w     28.00  82.00   1.00    1.00    --   40.98-125.00-180.00   54
 18  \w    -51.00  -7.00   1.00    1.00    --  -40.98 125.00-180.00   44
;
_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      0.1010898000
_diffrn_orient_matrix_UB_12      0.1333700000
_diffrn_orient_matrix_UB_13      0.0295930000
_diffrn_orient_matrix_UB_21      -0.1749867000
_diffrn_orient_matrix_UB_22      0.0171563000
_diffrn_orient_matrix_UB_23      0.0251087000
_diffrn_orient_matrix_UB_31      0.0253613000
_diffrn_orient_matrix_UB_32      -0.0478138000
_diffrn_orient_matrix_UB_33      0.0772960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.073
_diffrn_reflns_theta_min         2.481
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83692
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.1046
_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^)+(0.1907P)^2^+3.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3058
_refine_ls_wR_factor_ref         0.3130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5141
_reflns_number_total             6026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04892a2.cif
_cod_data_source_block           l2y-a
_cod_depositor_comments
'Adding full bibliography for 7244591--7244594.cif.'
_cod_database_code               7244591
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16B(H16C,H16D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C6B(H6B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B),
 C14B(H14B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17B(H17D,H17E,
 H17F), C18B(H18D,H18E,H18F), C19B(H19D,H19E,H19F)
;
_shelx_res_checksum              24230
_olex2_date_sample_data_collection 2019-05-20
_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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.832