#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:23:52 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293164 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248338.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_7248338
loop_
_publ_author_name
'Nie, Guihua'
'Tu, Ting'
'Liao, Tianhui'
'Liu, Donghan'
'Ye, Wenjun'
'Ren, Shi-Chao'
_publ_section_title
;
 N-heterocyclic carbene and photocatalyst-catalyzed rapid access to indole
 ketones via radical C(sp3)--H acylation
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              5397
_journal_page_last               5408
_journal_paper_doi               10.1039/D4GC00653D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.830(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9529(5)
_cell_length_b                   15.6474(6)
_cell_length_c                   10.0527(5)
_cell_measurement_reflns_used    6836
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.358
_cell_measurement_theta_min      2.433
_cell_volume                     1542.59(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.434
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1800 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.8525.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0627
_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)+(0.0318P)²+1.1843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2689
_reflns_number_total             3535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc00653d2.cif
_cod_data_source_block           mo_230919_ngh_c076_1a_zlj_0m
_cod_depositor_comments
'Adding full bibliography for 7248336--7248338.cif.'
_cod_database_code               7248338
_shelx_shelxl_version_number     2019/2
_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.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.969
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.78346(17) 0.38528(11) 0.47104(15) 0.0421(4) Uani 1 1 d . . . . .
N1 N 0.47350(17) 0.30420(11) 0.40543(17) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.4218(2) 0.07909(13) 0.3477(2) 0.0296(5) Uani 1 1 d . . . . .
H1 H 0.458959 0.027392 0.387733 0.036 Uiso 1 1 calc R U . . .
O2 O 0.97281(15) 0.64733(10) 0.93926(15) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.3194(2) 0.07702(15) 0.2361(2) 0.0349(5) Uani 1 1 d . . . . .
H2 H 0.286209 0.023460 0.199889 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2636(2) 0.15242(15) 0.1755(2) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.193220 0.149134 0.098931 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3088(2) 0.23136(15) 0.2248(2) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.271075 0.282381 0.182780 0.041 Uiso 1 1 calc R U . . .
C5 C 0.41122(19) 0.23427(13) 0.3376(2) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.47060(19) 0.15830(12) 0.40138(19) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.5731(2) 0.18690(12) 0.50995(19) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.57013(19) 0.27357(13) 0.5080(2) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.6599(2) 0.31621(12) 0.6230(2) 0.0264(4) Uani 1 1 d . . . . .
H9 H 0.604009 0.339842 0.688151 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7460(2) 0.23744(13) 0.6872(2) 0.0326(5) Uani 1 1 d . . . . .
H10A H 0.839095 0.239775 0.665073 0.039 Uiso 1 1 calc R U . . .
H10B H 0.753271 0.238340 0.786625 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6725(2) 0.15452(13) 0.6285(2) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.737673 0.113595 0.599608 0.035 Uiso 1 1 calc R U . . .
H11B H 0.624715 0.126477 0.695426 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4349(2) 0.39318(13) 0.3815(2) 0.0361(5) Uani 1 1 d . . . . .
H12A H 0.390347 0.400384 0.287408 0.054 Uiso 1 1 calc R U . . .
H12B H 0.516511 0.429208 0.399188 0.054 Uiso 1 1 calc R U . . .
H12C H 0.371712 0.409929 0.441712 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7541(2) 0.38454(13) 0.5841(2) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.81143(19) 0.44963(12) 0.68536(19) 0.0238(4) Uani 1 1 d . . . . .
C15 C 0.9023(2) 0.51013(14) 0.6486(2) 0.0308(5) Uani 1 1 d . . . . .
H15 H 0.927067 0.506902 0.561627 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9562(2) 0.57378(14) 0.7350(2) 0.0334(5) Uani 1 1 d . . . . .
H16 H 1.018771 0.613497 0.708463 0.040 Uiso 1 1 calc R U . . .
C17 C 0.91845(19) 0.58000(13) 0.8627(2) 0.0276(4) Uani 1 1 d . . . . .
C18 C 0.82981(19) 0.52069(13) 0.9023(2) 0.0269(4) Uani 1 1 d . . . . .
H18 H 0.804487 0.524539 0.989038 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7781(2) 0.45541(12) 0.8141(2) 0.0257(4) Uani 1 1 d . . . . .
H19 H 0.718930 0.414040 0.842313 0.031 Uiso 1 1 calc R U . . .
C20 C 0.9267(2) 0.66157(15) 1.0649(2) 0.0383(5) Uani 1 1 d . . . . .
H20A H 0.827414 0.668725 1.048388 0.057 Uiso 1 1 calc R U . . .
H20B H 0.969790 0.713259 1.107758 0.057 Uiso 1 1 calc R U . . .
H20C H 0.951336 0.612455 1.124624 0.057 Uiso 1 1 calc R U . . .
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
C5 N1 C12 126.46(17) . . ?
C8 N1 C5 107.03(16) . . ?
C8 N1 C12 126.24(18) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.4(2) . . ?
C6 C1 H1 120.3 . . ?
C17 O2 C20 117.57(17) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(2) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 129.37(19) . . ?
N1 C5 C6 108.76(17) . . ?
C4 C5 C6 121.87(19) . . ?
C1 C6 C5 118.16(18) . . ?
C1 C6 C7 136.29(19) . . ?
C5 C6 C7 105.54(17) . . ?
C6 C7 C11 141.87(18) . . ?
C8 C7 C6 106.89(18) . . ?
C8 C7 C11 111.01(18) . . ?
N1 C8 C9 132.60(18) . . ?
C7 C8 N1 111.78(18) . . ?
C7 C8 C9 115.29(18) . . ?
C8 C9 H9 110.2 . . ?
C8 C9 C10 100.33(16) . . ?
C8 C9 C13 115.48(17) . . ?
C10 C9 H9 110.2 . . ?
C13 C9 H9 110.2 . . ?
C13 C9 C10 109.93(16) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 C9 108.05(16) . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C7 C11 C10 102.89(16) . . ?
C7 C11 H11A 111.2 . . ?
C7 C11 H11B 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C9 120.23(19) . . ?
O1 C13 C14 120.45(18) . . ?
C14 C13 C9 119.31(17) . . ?
C15 C14 C13 118.24(17) . . ?
C19 C14 C13 123.86(18) . . ?
C19 C14 C15 117.88(18) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.67(19) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.62(19) . . ?
C17 C16 H16 120.2 . . ?
O2 C17 C16 115.43(18) . . ?
O2 C17 C18 124.53(19) . . ?
C18 C17 C16 120.03(19) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.54(18) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.21(18) . . ?
C18 C19 H19 119.4 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C13 1.221(2) . ?
N1 C5 1.379(3) . ?
N1 C8 1.371(3) . ?
N1 C12 1.453(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C1 C6 1.405(3) . ?
O2 C17 1.361(2) . ?
O2 C20 1.433(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.430(3) . ?
C6 C7 1.432(3) . ?
C7 C8 1.357(3) . ?
C7 C11 1.501(3) . ?
C8 C9 1.492(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.575(3) . ?
C9 C13 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.555(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.484(3) . ?
C14 C15 1.401(3) . ?
C14 C19 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.369(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.401(3) . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -1.6(3) . . . . ?
O1 C13 C14 C19 177.0(2) . . . . ?
N1 C5 C6 C1 -179.85(17) . . . . ?
N1 C5 C6 C7 -0.8(2) . . . . ?
N1 C8 C9 C10 -176.6(2) . . . . ?
N1 C8 C9 C13 -58.5(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 C8 179.5(2) . . . . ?
C1 C6 C7 C11 -7.0(4) . . . . ?
O2 C17 C18 C19 178.54(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 N1 179.9(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.51(18) . . . . ?
C5 N1 C8 C7 -0.1(2) . . . . ?
C5 N1 C8 C9 -172.9(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C11 174.2(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C7 C8 N1 -0.3(2) . . . . ?
C6 C7 C8 C9 173.80(15) . . . . ?
C6 C7 C11 C10 178.5(2) . . . . ?
C7 C8 C9 C10 10.8(2) . . . . ?
C7 C8 C9 C13 128.85(19) . . . . ?
C8 N1 C5 C4 -178.6(2) . . . . ?
C8 N1 C5 C6 0.6(2) . . . . ?
C8 C7 C11 C10 -8.1(2) . . . . ?
C8 C9 C10 C11 -15.1(2) . . . . ?
C8 C9 C13 O1 -21.4(3) . . . . ?
C8 C9 C13 C14 159.46(17) . . . . ?
C9 C10 C11 C7 14.5(2) . . . . ?
C9 C13 C14 C15 177.60(18) . . . . ?
C9 C13 C14 C19 -3.9(3) . . . . ?
C10 C9 C13 O1 91.2(2) . . . . ?
C10 C9 C13 C14 -88.0(2) . . . . ?
C11 C7 C8 N1 -176.05(16) . . . . ?
C11 C7 C8 C9 -1.9(2) . . . . ?
C12 N1 C5 C4 7.0(3) . . . . ?
C12 N1 C5 C6 -173.77(19) . . . . ?
C12 N1 C8 C7 174.21(19) . . . . ?
C12 N1 C8 C9 1.4(3) . . . . ?
C13 C9 C10 C11 -137.23(17) . . . . ?
C13 C14 C15 C16 177.94(19) . . . . ?
C13 C14 C19 C18 -176.59(18) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C14 C19 C18 2.0(3) . . . . ?
C15 C16 C17 O2 -177.39(19) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
C20 O2 C17 C16 173.82(19) . . . . ?
C20 O2 C17 C18 -5.2(3) . . . . ?
