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_7244593
_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         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.144(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7113(6)
_cell_length_b                   9.8511(5)
_cell_length_c                   25.2850(14)
_cell_measurement_reflns_used    5197
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      28.6730
_cell_measurement_theta_min      2.7900
_cell_volume                     2894.5(3)
_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 (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_environment      air
_diffrn_ambient_temperature      293.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -31.00  58.00   1.00    4.00    --  -11.59  57.00 -60.00   89
  2  \w     47.00  85.00   1.00    4.00    --   11.74  37.00-180.00   38
  3  \w     41.00  96.00   1.00    4.00    --   11.74 178.00-180.00   55
  4  \w    -20.00  22.00   1.00    4.00    --  -11.59 -99.00 120.00   42
;
_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      -0.0091647000
_diffrn_orient_matrix_UB_12      -0.0699451000
_diffrn_orient_matrix_UB_13      -0.0056358000
_diffrn_orient_matrix_UB_21      -0.0564181000
_diffrn_orient_matrix_UB_22      0.0051390000
_diffrn_orient_matrix_UB_23      0.0073186000
_diffrn_orient_matrix_UB_31      -0.0215023000
_diffrn_orient_matrix_UB_32      0.0162401000
_diffrn_orient_matrix_UB_33      -0.0267077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72112
_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    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0573P)^2^+1.3803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4201
_reflns_number_total             5094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04892a2.cif
_cod_data_source_block           indole2
_cod_depositor_comments
'Adding full bibliography for 7244591--7244594.cif.'
_cod_database_code               7244593
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C12B(H12B), C2(H2), C7B(H7B), C16B(H16B), C7(H7), C16(H16),
 C12(H12), C13B(H13B), C14B(H14B), C13(H13), C8B(H8B), C15B(H15B), C14(H14),
 C15(H15), C8(H8)
2.b Idealised Me refined as rotating group:
 C10B(H10D,H10E,H10F), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C9B(H9BA,H9BB,
 H9BC), C18(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_shelx_res_checksum              33377
_olex2_date_sample_data_collection 2019-01-25
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.740