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_7244594
_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      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             2019-05-29
_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                 110.655(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6474(9)
_cell_length_b                   7.3679(5)
_cell_length_c                   17.5437(13)
_cell_measurement_reflns_used    2583
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      3.7120
_cell_volume                     1529.7(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 (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      N~2~
_diffrn_ambient_temperature      99.99(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 0.969
_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      2.00  45.00   1.00    2.29    --   40.98 -38.00 120.00   43
  2  \w     23.00  69.00   1.00    2.29    --   40.98-125.00  30.00   46
  3  \w     36.00 135.00   1.00    4.00    --  106.95 -61.00 150.00   99
  4  \w    134.00 166.00   1.00    4.00    --  106.95  15.00   0.00   32
  5  \w     77.00 107.00   1.00    4.00    --  106.95-125.00 -60.00   30
  6  \w     34.00 114.00   1.00    4.00    --  106.95-125.00 120.00   80
  7  \w     55.00  86.00   1.00    4.00    --  106.95  15.00   0.00   31
  8  \w    -95.00 -18.00   1.00    2.29    --  -40.98 -57.00-120.00   77
  9  \w   -111.00 -23.00   1.00    2.29    --  -41.23 -39.00 134.00   88
 10  \w     23.00  48.00   1.00    2.29    --   41.23-125.00 -30.00   25
 11  \w     55.00  81.00   1.00    2.29    --   41.23-125.00 -30.00   26
 12  \w     99.00 128.00   1.00    4.00    --  106.95 -30.00 -90.00   29
 13  \w     41.00  82.00   1.00    4.00    --  106.95 -30.00 -90.00   41
 14  \w     85.00 164.00   1.00    4.00    --  106.95  61.00 -60.00   79
 15  \w     41.00  67.00   1.00    4.00    --  106.95 -77.00  60.00   26
;
_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      -0.0165832000
_diffrn_orient_matrix_UB_12      0.0888121000
_diffrn_orient_matrix_UB_13      -0.0827810000
_diffrn_orient_matrix_UB_21      -0.1211532000
_diffrn_orient_matrix_UB_22      0.0540606000
_diffrn_orient_matrix_UB_23      -0.0083104000
_diffrn_orient_matrix_UB_31      0.0445237000
_diffrn_orient_matrix_UB_32      0.1813832000
_diffrn_orient_matrix_UB_33      0.0434166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6302
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.501
_diffrn_reflns_theta_min         3.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79396
_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    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0560P)^2^+0.4510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2422
_reflns_number_total             2986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04892a2.cif
_cod_data_source_block           c2y-b
_cod_depositor_comments
'Adding full bibliography for 7244591--7244594.cif.'
_cod_database_code               7244594
_shelx_shelxl_version_number     2018/3
_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 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)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C10(H10), C7(H7), C11(H11), C8(H8), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2019-05-29
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.619