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#$Date: 2024-09-06 04:58:27 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160075.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_7160075
loop_
_publ_author_name
'Bettoni, Léo'
'Joly, Nicolas'
'Mendas, Inès'
'Moscogiuri, Matteo Maria'
'Lohier, Jean-François'
'Gaillard, Sylvain'
'Poater, Albert'
'Renaud, Jean-Luc'
_publ_section_title
;
 Iron-catalyzed synthesis of substituted 3-arylquinolin-2(1H)-ones
 via an intramolecular dehydrogenative coupling of amido-alcohols.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6933
_journal_page_last               6940
_journal_paper_doi               10.1039/d4ob00649f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_chemical_name_systematic
;
3-phenylquinolin-2(1H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-16 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.736(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8048(14)
_cell_length_b                   5.7547(5)
_cell_length_c                   21.5754(16)
_cell_measurement_reflns_used    9010
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      39.39
_cell_measurement_theta_min      2.38
_cell_volume                     2127.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32875
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         39.517
_diffrn_reflns_theta_min         2.377
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2016/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5643
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         6340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0793P)²+0.6013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4220
_reflns_number_total             6340
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00649f2.cif
_cod_data_source_block           bettoni8_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160074--7160075.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160075
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.40693(4) 0.05347(11) 0.43925(3) 0.02169(13) Uani 1 1 d . . . . .
N1 N 0.46156(4) 0.25279(12) 0.53091(3) 0.01763(13) Uani 1 1 d . . . . .
C1 C 0.46530(5) 0.43346(14) 0.57366(4) 0.01674(13) Uani 1 1 d . . . . .
C10 C 0.28430(4) 0.39658(13) 0.39554(4) 0.01653(13) Uani 1 1 d . . . . .
C8 C 0.34661(4) 0.41080(13) 0.45702(4) 0.01603(13) Uani 1 1 d . . . . .
C2 C 0.40964(4) 0.61255(14) 0.55780(4) 0.01633(13) Uani 1 1 d . . . . .
C9 C 0.40554(4) 0.22560(14) 0.47384(4) 0.01659(13) Uani 1 1 d . . . . .
C7 C 0.35098(5) 0.59424(13) 0.49759(4) 0.01663(13) Uani 1 1 d . . . . .
H7 H 0.313587 0.715312 0.485499 0.020 Uiso 1 1 calc R U . . .
C11 C 0.27131(5) 0.58297(15) 0.35227(4) 0.01973(15) Uani 1 1 d . . . . .
H11 H 0.303608 0.716879 0.361770 0.024 Uiso 1 1 calc R U . . .
C4 C 0.47244(5) 0.80203(17) 0.65864(4) 0.02315(16) Uani 1 1 d . . . . .
H4 H 0.475277 0.927499 0.687799 0.028 Uiso 1 1 calc R U . . .
C15 C 0.23530(5) 0.20261(15) 0.38110(4) 0.02134(15) Uani 1 1 d . . . . .
H15 H 0.243979 0.073961 0.409763 0.026 Uiso 1 1 calc R U . . .
C6 C 0.52449(5) 0.43876(16) 0.63174(4) 0.02097(16) Uani 1 1 d . . . . .
H6 H 0.561933 0.317279 0.642256 0.025 Uiso 1 1 calc R U . . .
C5 C 0.52771(5) 0.62279(17) 0.67350(4) 0.02408(17) Uani 1 1 d . . . . .
H5 H 0.567905 0.627906 0.712794 0.029 Uiso 1 1 calc R U . . .
C3 C 0.41376(5) 0.79630(15) 0.60154(4) 0.01951(15) Uani 1 1 d . . . . .
H3 H 0.376037 0.917167 0.591810 0.023 Uiso 1 1 calc R U . . .
C14 C 0.17409(5) 0.19639(17) 0.32527(4) 0.02510(17) Uani 1 1 d . . . . .
H14 H 0.140046 0.066155 0.316637 0.030 Uiso 1 1 calc R U . . .
C12 C 0.21125(5) 0.57333(16) 0.29529(4) 0.02254(16) Uani 1 1 d . . . . .
H12 H 0.203642 0.698697 0.265585 0.027 Uiso 1 1 calc R U . . .
C13 C 0.16254(5) 0.38069(17) 0.28192(4) 0.02474(18) Uani 1 1 d . . . . .
H13 H 0.121397 0.374704 0.243244 0.030 Uiso 1 1 calc R U . . .
H1 H 0.5015(8) 0.149(2) 0.5399(6) 0.031(3) Uiso 1 1 d . . . . .
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
C9 N1 C1 125.42(7) . . ?
N1 C1 C6 120.15(7) . . ?
N1 C1 C2 119.12(7) . . ?
C6 C1 C2 120.72(7) . . ?
C15 C10 C11 118.87(7) . . ?
C15 C10 C8 120.89(7) . . ?
C11 C10 C8 120.17(7) . . ?
C7 C8 C9 119.43(7) . . ?
C7 C8 C10 121.13(7) . . ?
C9 C8 C10 119.43(7) . . ?
C3 C2 C1 118.87(7) . . ?
C3 C2 C7 123.81(7) . . ?
C1 C2 C7 117.32(7) . . ?
O1 C9 N1 120.19(7) . . ?
O1 C9 C8 123.91(7) . . ?
N1 C9 C8 115.90(7) . . ?
C8 C7 C2 122.75(7) . . ?
C12 C11 C10 120.40(8) . . ?
C3 C4 C5 120.02(8) . . ?
C14 C15 C10 120.61(8) . . ?
C5 C6 C1 119.19(8) . . ?
C6 C5 C4 120.83(8) . . ?
C4 C3 C2 120.35(8) . . ?
C15 C14 C13 120.09(8) . . ?
C13 C12 C11 120.08(8) . . ?
C12 C13 C14 119.90(8) . . ?
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 C9 1.2444(10) . ?
N1 C9 1.3673(10) . ?
N1 C1 1.3794(11) . ?
C1 C6 1.4021(11) . ?
C1 C2 1.4063(11) . ?
C10 C15 1.3988(12) . ?
C10 C11 1.3994(11) . ?
C10 C8 1.4828(10) . ?
C8 C7 1.3599(11) . ?
C8 C9 1.4704(11) . ?
C2 C3 1.4058(11) . ?
C2 C7 1.4331(10) . ?
C11 C12 1.3947(11) . ?
C4 C3 1.3828(11) . ?
C4 C5 1.4015(13) . ?
C15 C14 1.3886(12) . ?
C6 C5 1.3815(13) . ?
C14 C13 1.3920(14) . ?
C12 C13 1.3887(14) . ?
