#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:38:39 +0300 (Thu, 05 May 2022) $
#$Revision: 274996 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244592.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244592
loop_
_publ_author_name
'Chen, Zhiyan'
'Huang, Wenbo'
'Yi, Liqi'
'Dong, Xiaohan'
'Sheng, Keyan'
'Li, Minghao'
'Bai, Rongxian'
'Sidorenko, A. Yu.'
'Huang, Jiang'
'Gu, Yanlong'
_publ_section_title
;
 Synthesis of indoles and carbazoles from a lignin model compound
 α-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      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             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                111.938(7)
_cell_angle_beta                 99.562(5)
_cell_angle_gamma                97.455(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2100(4)
_cell_length_b                   9.4039(6)
_cell_length_c                   10.1909(8)
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      28.8980
_cell_measurement_theta_min      2.3790
_cell_volume                     703.68(9)
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  85.00   1.00    1.50    --   11.74  57.00 -60.00  101
  2  ω    -21.00  88.00   1.00    1.50    --   11.74  77.00  60.00  109
  3  ω    -60.00  40.00   1.00    1.50    --   11.74 -57.00 150.00  100
  4  ω     35.00 101.00   1.00    1.50    --   11.74 178.00 150.00   66
  5  ω    -16.00  23.00   1.00    1.50    --   11.74  57.00-180.00   39
  6  ω    -20.00  53.00   1.00    1.50    --   11.74 -99.00 -30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0890164000
_diffrn_orient_matrix_UB_12      -0.0165020000
_diffrn_orient_matrix_UB_13      -0.0255270000
_diffrn_orient_matrix_UB_21      -0.0099388000
_diffrn_orient_matrix_UB_22      0.0107366000
_diffrn_orient_matrix_UB_23      0.0706877000
_diffrn_orient_matrix_UB_31      0.0024793000
_diffrn_orient_matrix_UB_32      0.0807995000
_diffrn_orient_matrix_UB_33      0.0174906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.216
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68891
_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    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0407
_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/[σ²(Fo²)+(0.0512P)²+0.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2148
_reflns_number_total             2474
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc04892a2.cif
_cod_data_source_block           indole1
_cod_depositor_comments
'Adding full bibliography for 7244591--7244594.cif.'
_cod_database_code               7244592
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 100.00
_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:
 C3(H3), C14(H14), C10(H10), C12(H12), C11(H11), C7(H7), C13(H13), C8(H8)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_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 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.737
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.68467(13) 0.02645(11) 0.21776(11) 0.0245(3) Uani 1 1 d . . . . .
O1 O 0.43700(14) -0.14253(13) 0.14497(13) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.35272(15) 0.41518(13) 0.71056(13) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.73544(17) 0.46487(16) 0.68519(15) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.59058(17) 0.33706(16) 0.58536(15) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.61512(18) 0.22334(16) 0.46134(15) 0.0182(3) Uani 1 1 d . . . . .
H3 H 0.722003 0.232306 0.442232 0.022 Uiso 1 1 calc R . . . .
C2 C 0.48727(18) 0.09421(16) 0.36185(15) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.32458(18) 0.07386(16) 0.38582(15) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.42487(18) 0.31895(16) 0.60724(15) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.78478(18) 0.49448(16) 0.83294(15) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.725568 0.433589 0.870563 0.023 Uiso 1 1 calc R . . . .
C10 C 0.82962(18) 0.55569(16) 0.63159(16) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.799939 0.536679 0.533498 0.023 Uiso 1 1 calc R . . . .
C12 C 1.01240(18) 0.70371(17) 0.86892(16) 0.0214(4) Uani 1 1 d . . . . .
H12 H 1.103774 0.783642 0.930146 0.026 Uiso 1 1 calc R . . . .
C11 C 0.96680(19) 0.67388(17) 0.72233(16) 0.0220(3) Uani 1 1 d . . . . .
H11 H 1.028446 0.733350 0.684866 0.026 Uiso 1 1 calc R . . . .
C17 C 0.52854(18) -0.01998(17) 0.23235(16) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.14568(18) 0.20789(17) 0.56330(16) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.040901 0.139343 0.523460 0.024 Uiso 1 1 calc R . . . .
C6 C 0.29608(18) 0.18806(16) 0.51110(15) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.92090(18) 0.61363(16) 0.92330(16) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.951152 0.633332 1.021522 0.024 Uiso 1 1 calc R . . . .
C16 C 0.17957(19) -0.05640(17) 0.28432(16) 0.0231(4) Uani 1 1 d . . . . .
H16A H 0.168067 -0.060405 0.187633 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.077394 -0.037763 0.315645 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.200504 -0.154328 0.284766 0.035 Uiso 1 1 calc GR . . . .
C8 C 0.18517(18) 0.34583(17) 0.68202(16) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.109521 0.387757 0.736584 0.025 Uiso 1 1 calc R . . . .
C15 C 0.42539(19) 0.57382(17) 0.81998(17) 0.0254(4) Uani 1 1 d . . . . .
H15A H 0.495162 0.568922 0.903041 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.336256 0.626076 0.849095 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.492562 0.630807 0.779778 0.038 Uiso 1 1 calc GR . . . .
C18 C 0.7329(2) -0.08257(18) 0.09579(17) 0.0275(4) Uani 1 1 d . . . . .
H18A H 0.661012 -0.092476 0.006988 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.721838 -0.183015 0.101186 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.848158 -0.044972 0.097823 0.041 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 C18 114.76(11) . . ?
C5 N1 C15 128.51(12) . . ?
C8 N1 C5 108.26(12) . . ?
C8 N1 C15 122.65(12) . . ?
C14 C9 C4 121.71(13) . . ?
C10 C9 C4 120.01(13) . . ?
C10 C9 C14 118.25(13) . . ?
C3 C4 C9 119.39(12) . . ?
C3 C4 C5 115.53(13) . . ?
C5 C4 C9 125.07(12) . . ?
C4 C3 H3 118.1 . . ?
C4 C3 C2 123.86(13) . . ?
C2 C3 H3 118.1 . . ?
C3 C2 C17 118.99(13) . . ?
C1 C2 C3 120.57(13) . . ?
C1 C2 C17 120.45(13) . . ?
C2 C1 C6 116.74(13) . . ?
C2 C1 C16 124.41(13) . . ?
C6 C1 C16 118.80(13) . . ?
N1 C5 C4 131.08(13) . . ?
N1 C5 C6 107.38(12) . . ?
C4 C5 C6 121.49(13) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.51(14) . . ?
C13 C14 H14 119.7 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.97(13) . . ?
C11 C10 H10 119.5 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C13 C12 C11 119.48(14) . . ?
C10 C11 C12 120.15(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C17 C2 112.53(12) . . ?
O1 C17 O2 121.16(13) . . ?
O1 C17 C2 126.31(14) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 H7 126.6 . . ?
C8 C7 C6 106.86(13) . . ?
C1 C6 C5 121.74(13) . . ?
C1 C6 C7 131.24(13) . . ?
C5 C6 C7 106.87(12) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.62(14) . . ?
C12 C13 H13 119.7 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C8 H8 124.7 . . ?
C7 C8 N1 110.61(13) . . ?
C7 C8 H8 124.7 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C17 1.3500(18) . ?
O2 C18 1.4387(17) . ?
O1 C17 1.2133(18) . ?
N1 C5 1.3831(18) . ?
N1 C8 1.3765(19) . ?
N1 C15 1.4594(18) . ?
C9 C4 1.486(2) . ?
C9 C14 1.401(2) . ?
C9 C10 1.394(2) . ?
C4 C3 1.383(2) . ?
C4 C5 1.414(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.414(2) . ?
C2 C1 1.399(2) . ?
C2 C17 1.481(2) . ?
C1 C6 1.406(2) . ?
C1 C16 1.501(2) . ?
C5 C6 1.418(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.387(2) . ?
C12 C13 1.383(2) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.430(2) . ?
C7 C8 1.356(2) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 H8 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
