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#$Date: 2023-06-15 11:51:30 +0300 (Thu, 15 Jun 2023) $
#$Revision: 284478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107373.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_8107373
loop_
_publ_author_name
'Liu, Yi'
'Liu, Feng'
'Chen, Yang'
'Yan, Xiaolong'
'Xiao, Tao'
_publ_section_title
;
 Synthesis and crystal structure of
 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              129
_journal_page_last               131
_journal_paper_doi               10.1515/ncrs-2022-0490
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C17 H11 F O3'
_chemical_formula_weight         282.26
_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
_cell_angle_alpha                90
_cell_angle_beta                 108.193(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1987(2)
_cell_length_b                   17.5458(3)
_cell_length_c                   8.5802(2)
_cell_measurement_reflns_used    5174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2350
_cell_measurement_theta_min      5.0240
_cell_volume                     1315.60(5)
_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 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.376
_diffrn_reflns_theta_min         5.041
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93560
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            corlorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0346
_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)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2282
_reflns_number_total             2636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0490_suppl.cif
_cod_data_source_block           X
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107373
_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   0.841
_shelx_estimated_absorpt_t_max   0.916
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 0.13907(9) 0.21053(4) 0.96057(10) 0.0208(2) Uani 1 1 d . . . . .
C1 C 0.24833(12) 0.24545(6) 0.90922(13) 0.0189(3) Uani 1 1 d . . . . .
O2 O 0.16022(11) 0.44262(5) 0.92851(12) 0.0308(2) Uani 1 1 d . . . . .
C2 C 0.25961(12) 0.32140(6) 0.89753(14) 0.0207(3) Uani 1 1 d . . . . .
H2A H 0.3371 0.3416 0.8617 0.025 Uiso 1 1 calc R U . . .
O3 O 0.47612(10) 0.18074(5) 1.15504(10) 0.0272(2) Uani 1 1 d . . . . .
C3 C 0.15398(13) 0.37269(7) 0.93941(14) 0.0212(3) Uani 1 1 d . . . . .
F F 0.49913(10) 0.09392(4) 0.71310(9) 0.0345(2) Uani 1 1 d . . . . .
C4 C 0.03775(12) 0.33442(6) 0.99640(13) 0.0188(3) Uani 1 1 d . . . . .
C5 C -0.07314(13) 0.37558(7) 1.04359(14) 0.0225(3) Uani 1 1 d . . . . .
H5A H -0.0746 0.4285 1.0380 0.027 Uiso 1 1 calc R U . . .
C6 C -0.17909(14) 0.33804(7) 1.09783(16) 0.0264(3) Uani 1 1 d . . . . .
H6A H -0.2520 0.3656 1.1287 0.032 Uiso 1 1 calc R U . . .
C7 C -0.17765(13) 0.25808(7) 1.10688(16) 0.0267(3) Uani 1 1 d . . . . .
H7A H -0.2488 0.2331 1.1454 0.032 Uiso 1 1 calc R U . . .
C8 C -0.07178(13) 0.21637(7) 1.05926(15) 0.0234(3) Uani 1 1 d . . . . .
H8A H -0.0720 0.1634 1.0635 0.028 Uiso 1 1 calc R U . . .
C9 C 0.03548(12) 0.25497(7) 1.00475(13) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.35136(13) 0.18836(6) 0.86772(14) 0.0201(3) Uani 1 1 d . . . . .
H10A H 0.4041 0.2123 0.7989 0.024 Uiso 1 1 calc R U . . .
H10B H 0.2901 0.1469 0.8059 0.024 Uiso 1 1 calc R U . . .
C11 C 0.46848(12) 0.15642(6) 1.02013(14) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.57831(12) 0.09619(6) 1.00437(15) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.59231(14) 0.06808(7) 0.85820(15) 0.0241(3) Uani 1 1 d . . . . .
C14 C 0.70054(15) 0.01417(7) 0.85227(18) 0.0310(3) Uani 1 1 d . . . . .
H14A H 0.7070 -0.0033 0.7523 0.037 Uiso 1 1 calc R U . . .
C15 C 0.79879(15) -0.01304(7) 0.9988(2) 0.0345(3) Uani 1 1 d . . . . .
H15A H 0.8725 -0.0491 0.9975 0.041 Uiso 1 1 calc R U . . .
C16 C 0.78827(15) 0.01296(7) 1.14764(19) 0.0335(3) Uani 1 1 d . . . . .
H16A H 0.8546 -0.0056 1.2456 0.040 Uiso 1 1 calc R U . . .
C17 C 0.67896(14) 0.06658(7) 1.14991(16) 0.0259(3) Uani 1 1 d . . . . .
H17A H 0.6720 0.0834 1.2501 0.031 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'
F F 0.0727 0.0534 '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
C1 O1 C9 118.65(9) . .
C2 C1 O1 123.54(10) . .
C2 C1 C10 125.24(10) . .
O1 C1 C10 111.22(9) . .
C1 C2 C3 121.61(10) . .
C1 C2 H2A 119.2 . .
C3 C2 H2A 119.2 . .
O2 C3 C2 123.25(11) . .
O2 C3 C4 122.40(10) . .
C2 C3 C4 114.35(10) . .
C9 C4 C5 118.26(10) . .
C9 C4 C3 119.82(10) . .
C5 C4 C3 121.92(10) . .
C6 C5 C4 120.40(11) . .
C6 C5 H5A 119.8 . .
C4 C5 H5A 119.8 . .
C5 C6 C7 120.17(10) . .
C5 C6 H6A 119.9 . .
C7 C6 H6A 119.9 . .
C8 C7 C6 120.61(11) . .
C8 C7 H7A 119.7 . .
C6 C7 H7A 119.7 . .
C7 C8 C9 118.79(11) . .
C7 C8 H8A 120.6 . .
C9 C8 H8A 120.6 . .
O1 C9 C8 116.24(10) . .
O1 C9 C4 122.01(10) . .
C8 C9 C4 121.75(10) . .
C1 C10 C11 111.96(9) . .
C1 C10 H10A 109.2 . .
C11 C10 H10A 109.2 . .
C1 C10 H10B 109.2 . .
C11 C10 H10B 109.2 . .
H10A C10 H10B 107.9 . .
O3 C11 C12 119.61(10) . .
O3 C11 C10 120.35(10) . .
C12 C11 C10 120.01(9) . .
C13 C12 C17 116.78(11) . .
C13 C12 C11 125.94(11) . .
C17 C12 C11 117.25(10) . .
F C13 C14 116.86(11) . .
F C13 C12 120.10(10) . .
C14 C13 C12 123.04(12) . .
C15 C14 C13 118.35(12) . .
C15 C14 H14A 120.8 . .
C13 C14 H14A 120.8 . .
C14 C15 C16 120.61(11) . .
C14 C15 H15A 119.7 . .
C16 C15 H15A 119.7 . .
C17 C16 C15 119.80(13) . .
C17 C16 H16A 120.1 . .
C15 C16 H16A 120.1 . .
C16 C17 C12 121.40(13) . .
C16 C17 H17A 119.3 . .
C12 C17 H17A 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3624(13) .
O1 C9 1.3731(13) .
C1 C2 1.3428(16) .
C1 C10 1.4964(14) .
O2 C3 1.2331(15) .
C2 C3 1.4497(15) .
C2 H2A 0.9300 .
O3 C11 1.2150(14) .
C3 C4 1.4696(15) .
F C13 1.3505(15) .
C4 C9 1.3962(17) .
C4 C5 1.4085(15) .
C5 C6 1.3723(16) .
C5 H5A 0.9300 .
C6 C7 1.4050(19) .
C6 H6A 0.9300 .
C7 C8 1.3783(16) .
C7 H7A 0.9300 .
C8 C9 1.3926(16) .
C8 H8A 0.9300 .
C10 C11 1.5182(15) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.4969(15) .
C12 C13 1.3906(17) .
C12 C17 1.4017(17) .
C13 C14 1.3857(16) .
C14 C15 1.384(2) .
C14 H14A 0.9300 .
C15 C16 1.388(2) .
C15 H15A 0.9300 .
C16 C17 1.3815(18) .
C16 H16A 0.9300 .
C17 H17A 0.9300 .
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 -0.76(16) . . . .
C9 O1 C1 C10 179.53(8) . . . .
O1 C1 C2 C3 -0.08(18) . . . .
C10 C1 C2 C3 179.59(10) . . . .
C1 C2 C3 O2 -179.25(11) . . . .
C1 C2 C3 C4 0.73(16) . . . .
O2 C3 C4 C9 179.40(11) . . . .
C2 C3 C4 C9 -0.59(15) . . . .
O2 C3 C4 C5 -0.59(17) . . . .
C2 C3 C4 C5 179.43(10) . . . .
C9 C4 C5 C6 0.68(17) . . . .
C3 C4 C5 C6 -179.33(11) . . . .
C4 C5 C6 C7 0.07(18) . . . .
C5 C6 C7 C8 -0.99(19) . . . .
C6 C7 C8 C9 1.12(18) . . . .
C1 O1 C9 C8 -178.80(9) . . . .
C1 O1 C9 C4 0.89(15) . . . .
C7 C8 C9 O1 179.33(10) . . . .
C7 C8 C9 C4 -0.35(17) . . . .
C5 C4 C9 O1 179.79(9) . . . .
C3 C4 C9 O1 -0.20(16) . . . .
C5 C4 C9 C8 -0.54(16) . . . .
C3 C4 C9 C8 179.47(10) . . . .
C2 C1 C10 C11 102.52(13) . . . .
O1 C1 C10 C11 -77.77(11) . . . .
C1 C10 C11 O3 -4.06(15) . . . .
C1 C10 C11 C12 177.69(9) . . . .
O3 C11 C12 C13 -173.80(11) . . . .
C10 C11 C12 C13 4.47(16) . . . .
O3 C11 C12 C17 4.56(15) . . . .
C10 C11 C12 C17 -177.17(10) . . . .
C17 C12 C13 F 179.95(10) . . . .
C11 C12 C13 F -1.69(17) . . . .
C17 C12 C13 C14 -0.85(17) . . . .
C11 C12 C13 C14 177.51(11) . . . .
F C13 C14 C15 179.45(11) . . . .
C12 C13 C14 C15 0.22(18) . . . .
C13 C14 C15 C16 0.27(19) . . . .
C14 C15 C16 C17 -0.08(19) . . . .
C15 C16 C17 C12 -0.59(19) . . . .
C13 C12 C17 C16 1.03(17) . . . .
C11 C12 C17 C16 -177.48(10) . . . .
