#------------------------------------------------------------------------------
#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/81/7128155.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_7128155
loop_
_publ_author_name
'Hu, Yan'
'Nan, Jiang'
'Gong, Xue'
'Zhang, Jiawen'
'Yin, Jiacheng'
'Ma, Yangmin'
_publ_section_title
;
 Zinc-catalyzed C-H alkenylation of quinoline N-oxides with ynones:
 a new strategy towards quinoline-enol scaffolds.
;
_journal_issue                   40
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4930
_journal_page_last               4933
_journal_paper_doi               10.1039/d1cc00245g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-10 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.874(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6333(12)
_cell_length_b                   5.5710(5)
_cell_length_c                   20.8717(18)
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      3.30
_cell_volume                     1437.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22330
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_min         3.296
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0649
_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)+(0.1000P)²+0.6035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.2311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1806
_reflns_number_total             3547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00245g2.cif
_cod_data_source_block           sust_2837_0m_a
_cod_depositor_comments          'Adding full bibliography for 7128155.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7128155
_shelx_shelxl_version_number     2018/3
_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_min   0.983
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O2 O 0.60419(15) 0.1606(3) 0.12876(8) 0.0644(5) Uani 1 1 d . . . . .
O1 O 0.54789(16) 0.1074(3) 0.42240(9) 0.0663(6) Uani 1 1 d . . . . .
H1 H 0.553651 0.135035 0.461554 0.099 Uiso 1 1 calc R U . . .
N1 N 0.60891(16) 0.3293(4) 0.53300(10) 0.0554(5) Uani 1 1 d . . . . .
C1 C 0.72753(18) 0.6700(4) 0.54060(12) 0.0495(6) Uani 1 1 d . . . . .
C12 C 0.59904(19) 0.1770(4) 0.19343(11) 0.0503(6) Uani 1 1 d . . . . .
C13 C 0.60112(18) 0.2408(4) 0.32695(11) 0.0482(6) Uani 1 1 d . . . . .
C2 C 0.66470(18) 0.4825(4) 0.50127(12) 0.0492(6) Uani 1 1 d . . . . .
C10 C 0.65969(19) 0.4503(4) 0.43494(12) 0.0518(6) Uani 1 1 d . . . . .
H10 H 0.697455 0.553883 0.412798 0.062 Uiso 1 1 d R U . . .
C11 C 0.60101(19) 0.2620(4) 0.39766(12) 0.0516(6) Uani 1 1 d . . . . .
C3 C 0.7274(2) 0.6812(5) 0.60792(13) 0.0558(6) Uani 1 1 d . . . . .
C4 C 0.7891(2) 0.8366(5) 0.51376(14) 0.0598(7) Uani 1 1 d . . . . .
H4 H 0.789206 0.830971 0.469239 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6489(2) 0.4044(4) 0.29164(12) 0.0553(6) Uani 1 1 d . . . . .
H14 H 0.682431 0.539335 0.312967 0.066 Uiso 1 1 calc R U . . .
C15 C 0.6486(2) 0.3745(5) 0.22664(12) 0.0581(7) Uani 1 1 d . . . . .
H15 H 0.681878 0.487755 0.204665 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5502(2) 0.0116(5) 0.22650(14) 0.0667(8) Uani 1 1 d . . . . .
H16 H 0.516294 -0.122018 0.204684 0.080 Uiso 1 1 calc R U . . .
C5 C 0.6081(2) 0.3446(5) 0.59771(14) 0.0658(7) Uani 1 1 d . . . . .
H5 H 0.567073 0.235895 0.616129 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5515(2) 0.0439(5) 0.29195(13) 0.0683(8) Uani 1 1 d . . . . .
H17 H 0.518098 -0.069983 0.313667 0.082 Uiso 1 1 calc R U . . .
C6 C 0.6654(2) 0.5136(5) 0.63577(14) 0.0662(7) Uani 1 1 d . . . . .
H6 H 0.664422 0.520721 0.680156 0.079 Uiso 1 1 calc R U . . .
C7 C 0.7903(2) 0.8602(6) 0.64607(15) 0.0718(8) Uani 1 1 d . . . . .
H7 H 0.791277 0.869537 0.690681 0.086 Uiso 1 1 calc R U . . .
C8 C 0.8492(2) 1.0078(5) 0.55208(16) 0.0730(8) Uani 1 1 d . . . . .
H8 H 0.889992 1.116680 0.533568 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5588(3) -0.0470(6) 0.09381(14) 0.0772(9) Uani 1 1 d . . . . .
H18A H 0.591919 -0.188267 0.115507 0.116 Uiso 1 1 calc R U . . .
H18B H 0.571371 -0.041524 0.050026 0.116 Uiso 1 1 calc R U . . .
H18C H 0.482322 -0.051292 0.092344 0.116 Uiso 1 1 calc R U . . .
C9 C 0.8493(2) 1.0189(6) 0.61839(17) 0.0781(9) Uani 1 1 d . . . . .
H9 H 0.890025 1.135806 0.644172 0.094 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
C12 O2 C18 117.6(2) . . ?
C11 O1 H1 109.5 . . ?
C5 N1 C2 123.8(2) . . ?
C4 C1 C3 119.0(2) . . ?
C4 C1 C2 122.2(2) . . ?
C3 C1 C2 118.8(2) . . ?
O2 C12 C16 124.7(2) . . ?
O2 C12 C15 116.1(2) . . ?
C16 C12 C15 119.2(2) . . ?
C14 C13 C17 115.9(2) . . ?
C14 C13 C11 124.6(2) . . ?
C17 C13 C11 119.5(2) . . ?
N1 C2 C10 118.9(2) . . ?
N1 C2 C1 116.8(2) . . ?
C10 C2 C1 124.3(2) . . ?
C2 C10 C11 123.7(2) . . ?
C2 C10 H10 119.6 . . ?
C11 C10 H10 116.7 . . ?
O1 C11 C10 122.7(2) . . ?
O1 C11 C13 117.5(2) . . ?
C10 C11 C13 119.8(2) . . ?
C1 C3 C7 118.5(3) . . ?
C1 C3 C6 119.7(2) . . ?
C7 C3 C6 121.8(3) . . ?
C8 C4 C1 121.0(3) . . ?
C8 C4 H4 119.5 . . ?
C1 C4 H4 119.5 . . ?
C15 C14 C13 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C12 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C12 C15 H15 119.9 . . ?
C12 C16 C17 119.8(2) . . ?
C12 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C6 C5 N1 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
N1 C5 H5 119.4 . . ?
C16 C17 C13 122.4(2) . . ?
C16 C17 H17 118.8 . . ?
C13 C17 H17 118.8 . . ?
C5 C6 C3 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C3 C6 H6 120.2 . . ?
C9 C7 C3 120.9(3) . . ?
C9 C7 H7 119.6 . . ?
C3 C7 H7 119.6 . . ?
C4 C8 C9 120.1(3) . . ?
C4 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C9 C8 120.5(3) . . ?
C7 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
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 C12 1.368(3) . ?
O2 C18 1.424(3) . ?
O1 C11 1.265(3) . ?
O1 H1 0.8200 . ?
N1 C5 1.355(3) . ?
N1 C2 1.362(3) . ?
C1 C4 1.400(3) . ?
C1 C3 1.407(3) . ?
C1 C2 1.459(3) . ?
C12 C16 1.371(4) . ?
C12 C15 1.380(3) . ?
C13 C14 1.386(3) . ?
C13 C17 1.394(3) . ?
C13 C11 1.481(3) . ?
C2 C10 1.385(3) . ?
C10 C11 1.421(3) . ?
C10 H10 0.9300 . ?
C3 C7 1.414(4) . ?
C3 C6 1.418(4) . ?
C4 C8 1.370(4) . ?
C4 H4 0.9300 . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C5 C6 1.344(4) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352667
