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#$Date: 2023-09-28 10:34:56 +0300 (Thu, 28 Sep 2023) $
#$Revision: 286575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107564.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_8107564
loop_
_publ_author_name
'Liu, Yi'
'Zhao, Zhimeng'
'Zhang, Yuming'
'Liu, Feng'
'Chen, Yang'
'Xiao, Tao'
_publ_section_title
;
 Synthesis and crystal structure of
 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              795
_journal_page_last               796
_journal_paper_doi               10.1515/ncrs-2023-0214
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29
_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
_cell_angle_alpha                86.8770(10)
_cell_angle_beta                 78.9440(10)
_cell_angle_gamma                68.9080(10)
_cell_formula_units_Z            2
_cell_length_a                   7.75390(10)
_cell_length_b                   8.26060(10)
_cell_length_c                   11.6271(2)
_cell_measurement_reflns_used    8871
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.7940
_cell_measurement_theta_min      5.7400
_cell_volume                     681.861(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.212
_diffrn_reflns_theta_min         3.874
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85972
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0518
_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+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2468
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0214_suppl_001.cif
_cod_data_source_block           X
_cod_database_code               8107564
_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   0.865
_shelx_estimated_absorpt_t_max   0.929
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
O1 O 0.46691(17) 0.16852(15) 0.40464(10) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.3953(2) 0.2687(2) 0.50584(14) 0.0188(4) Uani 1 1 d . . . . .
O2 O 0.82551(17) 0.26213(17) 0.58562(11) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.2013(2) 0.3271(2) 0.54143(15) 0.0213(4) Uani 1 1 d . . . . .
H2A H 0.1264 0.2987 0.4984 0.026 Uiso 1 1 calc R U . . .
O3 O 0.6343(2) 0.26500(16) 0.15787(11) 0.0305(4) Uani 1 1 d . . . . .
C3 C 0.1218(2) 0.4285(2) 0.64231(15) 0.0229(4) Uani 1 1 d . . . . .
H3A H -0.0078 0.4675 0.6678 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2340(3) 0.4731(2) 0.70644(15) 0.0225(4) Uani 1 1 d . . . . .
H4A H 0.1787 0.5438 0.7729 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4267(2) 0.4120(2) 0.67082(14) 0.0205(4) Uani 1 1 d . . . . .
H5A H 0.5011 0.4406 0.7141 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5113(2) 0.3069(2) 0.56980(14) 0.0185(4) Uani 1 1 d . . . . .
C7 C 0.7166(2) 0.2355(2) 0.53099(14) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.7786(2) 0.1291(2) 0.42531(15) 0.0218(4) Uani 1 1 d . . . . .
H8A H 0.9068 0.0779 0.3964 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6566(2) 0.1022(2) 0.36803(14) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.7077(3) -0.0034(2) 0.25822(15) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.6287 -0.0729 0.2641 0.027 Uiso 1 1 calc R U . . .
H10B H 0.8372 -0.0821 0.2502 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6848(2) 0.1084(2) 0.14877(15) 0.0216(4) Uani 1 1 d . . . . .
C12 C 0.7278(2) 0.0168(2) 0.03357(15) 0.0208(4) Uani 1 1 d . . . . .
C13 C 0.7397(3) -0.1567(2) 0.03145(16) 0.0248(4) Uani 1 1 d . . . . .
H13A H 0.7276 -0.2143 0.1018 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7689(3) -0.2438(2) -0.07283(16) 0.0280(4) Uani 1 1 d . . . . .
H14A H 0.7761 -0.3586 -0.0726 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7874(3) -0.1582(2) -0.17785(16) 0.0292(4) Uani 1 1 d . . . . .
H15A H 0.8049 -0.2148 -0.2485 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7797(3) 0.0121(2) -0.17719(16) 0.0264(4) Uani 1 1 d . . . . .
H16A H 0.7947 0.0673 -0.2483 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7503(2) 0.1033(2) -0.07342(15) 0.0227(4) Uani 1 1 d . . . . .
C18 C 0.7459(3) 0.2874(2) -0.08228(16) 0.0290(4) Uani 1 1 d . . . . .
H18A H 0.7248 0.3347 -0.0050 0.043 Uiso 1 1 calc R U . . .
H18B H 0.8639 0.2888 -0.1257 0.043 Uiso 1 1 calc R U . . .
H18C H 0.6462 0.3560 -0.1218 0.043 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C9 O1 C1 118.68(13) . .
O1 C1 C2 116.12(14) . .
O1 C1 C6 121.97(15) . .
C2 C1 C6 121.91(16) . .
C3 C2 C1 118.56(15) . .
C3 C2 H2A 120.7 . .
C1 C2 H2A 120.7 . .
C2 C3 C4 120.83(16) . .
C2 C3 H3A 119.6 . .
C4 C3 H3A 119.6 . .
C5 C4 C3 119.86(16) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
C4 C5 C6 120.52(15) . .
C4 C5 H5A 119.7 . .
C6 C5 H5A 119.7 . .
C1 C6 C5 118.28(15) . .
C1 C6 C7 119.71(15) . .
C5 C6 C7 122.01(15) . .
O2 C7 C8 123.36(16) . .
O2 C7 C6 122.33(15) . .
C8 C7 C6 114.30(14) . .
C9 C8 C7 121.93(16) . .
C9 C8 H8A 119.0 . .
C7 C8 H8A 119.0 . .
C8 C9 O1 123.38(15) . .
C8 C9 C10 125.54(16) . .
O1 C9 C10 111.08(14) . .
C9 C10 C11 112.61(14) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
O3 C11 C12 122.72(15) . .
O3 C11 C10 119.85(15) . .
C12 C11 C10 117.43(14) . .
C13 C12 C17 119.26(16) . .
C13 C12 C11 119.44(15) . .
C17 C12 C11 121.27(15) . .
C14 C13 C12 121.51(17) . .
C14 C13 H13A 119.2 . .
C12 C13 H13A 119.2 . .
C13 C14 C15 119.34(17) . .
C13 C14 H14A 120.3 . .
C15 C14 H14A 120.3 . .
C16 C15 C14 119.78(16) . .
C16 C15 H15A 120.1 . .
C14 C15 H15A 120.1 . .
C15 C16 C17 122.16(17) . .
C15 C16 H16A 118.9 . .
C17 C16 H16A 118.9 . .
C16 C17 C12 117.94(16) . .
C16 C17 C18 118.01(16) . .
C12 C17 C18 124.05(16) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 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
O1 C9 1.360(2) .
O1 C1 1.3794(19) .
C1 C2 1.388(2) .
C1 C6 1.396(2) .
O2 C7 1.233(2) .
C2 C3 1.384(2) .
C2 H2A 0.9300 .
O3 C11 1.213(2) .
C3 C4 1.399(2) .
C3 H3A 0.9300 .
C4 C5 1.379(2) .
C4 H4A 0.9300 .
C5 C6 1.403(2) .
C5 H5A 0.9300 .
C6 C7 1.471(2) .
C7 C8 1.450(2) .
C8 C9 1.341(2) .
C8 H8A 0.9300 .
C9 C10 1.492(2) .
C10 C11 1.531(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.495(2) .
C12 C13 1.404(2) .
C12 C17 1.413(2) .
C13 C14 1.382(2) .
C13 H13A 0.9300 .
C14 C15 1.387(3) .
C14 H14A 0.9300 .
C15 C16 1.387(3) .
C15 H15A 0.9300 .
C16 C17 1.395(2) .
C16 H16A 0.9300 .
C17 C18 1.507(2) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
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
C9 O1 C1 C2 -177.53(13) . . . .
C9 O1 C1 C6 1.5(2) . . . .
O1 C1 C2 C3 -179.88(13) . . . .
C6 C1 C2 C3 1.1(2) . . . .
C1 C2 C3 C4 0.7(2) . . . .
C2 C3 C4 C5 -1.7(3) . . . .
C3 C4 C5 C6 0.8(2) . . . .
O1 C1 C6 C5 179.07(13) . . . .
C2 C1 C6 C5 -2.0(2) . . . .
O1 C1 C6 C7 -1.6(2) . . . .
C2 C1 C6 C7 177.35(14) . . . .
C4 C5 C6 C1 1.0(2) . . . .
C4 C5 C6 C7 -178.31(14) . . . .
C1 C6 C7 O2 -178.41(15) . . . .
C5 C6 C7 O2 0.9(3) . . . .
C1 C6 C7 C8 0.3(2) . . . .
C5 C6 C7 C8 179.60(14) . . . .
O2 C7 C8 C9 179.81(16) . . . .
C6 C7 C8 C9 1.1(2) . . . .
C7 C8 C9 O1 -1.3(3) . . . .
C7 C8 C9 C10 179.25(15) . . . .
C1 O1 C9 C8 0.0(2) . . . .
C1 O1 C9 C10 179.50(12) . . . .
C8 C9 C10 C11 -100.7(2) . . . .
O1 C9 C10 C11 79.83(17) . . . .
C9 C10 C11 O3 1.6(2) . . . .
C9 C10 C11 C12 -178.63(14) . . . .
O3 C11 C12 C13 -164.27(17) . . . .
C10 C11 C12 C13 16.0(2) . . . .
O3 C11 C12 C17 13.6(3) . . . .
C10 C11 C12 C17 -166.17(15) . . . .
C17 C12 C13 C14 -1.4(3) . . . .
C11 C12 C13 C14 176.45(16) . . . .
C12 C13 C14 C15 0.2(3) . . . .
C13 C14 C15 C16 1.1(3) . . . .
C14 C15 C16 C17 -1.2(3) . . . .
C15 C16 C17 C12 -0.1(3) . . . .
C15 C16 C17 C18 179.52(16) . . . .
C13 C12 C17 C16 1.3(3) . . . .
C11 C12 C17 C16 -176.48(15) . . . .
C13 C12 C17 C18 -178.21(16) . . . .
C11 C12 C17 C18 4.0(3) . . . .
