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#$Date: 2023-05-05 04:09:58 +0300 (Fri, 05 May 2023) $
#$Revision: 283179 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/87/1568780.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_1568780
loop_
_publ_author_name
'Mavroskoufis, Andreas'
'Lohani, Manish'
'Weber, Manuela'
'Hopkinson, Matthew N.'
'Götze, Jan P'
_publ_section_title
;
 A (TD-)DFT study on photo-NHC catalysis: photoenolization/Diels-Alder
 reaction of acid fluorides catalyzed by N-heterocyclic carbenes.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              4027
_journal_page_last               4037
_journal_paper_doi               10.1039/d2sc04732b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C22 H15 F3 O2'
_chemical_formula_weight         368.34
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2bv0t1
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-02 deposited with the CCDC.	2023-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0695(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6916(2)
_cell_length_b                   13.1235(2)
_cell_length_c                   13.3856(2)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.63
_cell_volume                     1689.54(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30101
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         2.181
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.9585
_exptl_transmission_factor_min   0.9217
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0326
_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)+(0.0321P)²+0.9040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             3458
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04732b2.cif
_cod_data_source_block           AM0328SC
_cod_depositor_comments
'Adding full bibliography for 1568779--1568781.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568780
_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   0.969
_shelx_estimated_absorpt_t_max   0.983
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
F1 F 0.84370(7) 0.46872(6) 0.12896(5) 0.02295(18) Uani 1 1 d . . . . .
F2 F 0.64599(8) 0.52585(6) 0.06366(5) 0.02317(18) Uani 1 1 d . . . . .
F3 F 0.68659(8) 0.36439(6) 0.06450(6) 0.02440(18) Uani 1 1 d . . . . .
O1 O 0.83904(9) 0.63800(6) 0.35002(7) 0.0201(2) Uani 1 1 d . . . . .
O2 O 0.68251(8) 0.53623(6) 0.27097(6) 0.01503(18) Uani 1 1 d . . . . .
C1 C 0.81170(12) 0.55229(9) 0.32250(9) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.90583(12) 0.46419(9) 0.34273(9) 0.0152(2) Uani 1 1 d . . . . .
C3 C 1.04414(13) 0.48127(10) 0.38225(9) 0.0182(3) Uani 1 1 d . . . . .
H3 H 1.076675 0.548681 0.396205 0.022 Uiso 1 1 calc R U . . .
C4 C 1.13326(13) 0.39942(10) 0.40090(9) 0.0208(3) Uani 1 1 d . . . . .
H4 H 1.227861 0.410490 0.426616 0.025 Uiso 1 1 calc R U . . .
C5 C 1.08438(13) 0.30085(10) 0.38199(10) 0.0209(3) Uani 1 1 d . . . . .
H5 H 1.145803 0.244737 0.395348 0.025 Uiso 1 1 calc R U . . .
C6 C 0.94665(13) 0.28369(9) 0.34376(9) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.913894 0.216022 0.331774 0.022 Uiso 1 1 calc R U . . .
C7 C 0.85658(12) 0.36561(9) 0.32299(9) 0.0147(2) Uani 1 1 d . . . . .
C8 C 0.70527(12) 0.34871(9) 0.28365(9) 0.0136(2) Uani 1 1 d . . . . .
H8 H 0.699520 0.287676 0.238603 0.016 Uiso 1 1 calc R U . . .
C9 C 0.64679(12) 0.44093(9) 0.22031(9) 0.0140(2) Uani 1 1 d . . . . .
C10 C 0.62212(12) 0.32570(9) 0.37095(9) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.70630(12) 0.44976(9) 0.11848(9) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.48893(12) 0.43704(9) 0.19678(9) 0.0151(2) Uani 1 1 d . . . . .
C13 C 0.40706(13) 0.52087(10) 0.21333(9) 0.0181(3) Uani 1 1 d . . . . .
H13 H 0.449334 0.581872 0.240274 0.022 Uiso 1 1 calc R U . . .
C14 C 0.26329(13) 0.51550(11) 0.19049(10) 0.0230(3) Uani 1 1 d . . . . .
H14 H 0.207517 0.572478 0.203135 0.028 Uiso 1 1 calc R U . . .
C15 C 0.20113(13) 0.42763(11) 0.14945(10) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.102921 0.424195 0.133900 0.030 Uiso 1 1 calc R U . . .
C16 C 0.28262(14) 0.34474(11) 0.13113(10) 0.0240(3) Uani 1 1 d . . . . .
H16 H 0.240164 0.284648 0.102129 0.029 Uiso 1 1 calc R U . . .
C17 C 0.42599(13) 0.34886(10) 0.15487(9) 0.0193(3) Uani 1 1 d . . . . .
H17 H 0.481274 0.291516 0.142542 0.023 Uiso 1 1 calc R U . . .
C18 C 0.62110(13) 0.39256(9) 0.45156(9) 0.0188(3) Uani 1 1 d . . . . .
H18 H 0.674685 0.453300 0.453418 0.023 Uiso 1 1 calc R U . . .
C19 C 0.54286(14) 0.37169(10) 0.52927(10) 0.0217(3) Uani 1 1 d . . . . .
H19 H 0.541947 0.418817 0.583056 0.026 Uiso 1 1 calc R U . . .
C20 C 0.46605(13) 0.28257(10) 0.52898(10) 0.0213(3) Uani 1 1 d . . . . .
H20 H 0.411858 0.268633 0.581893 0.026 Uiso 1 1 calc R U . . .
C21 C 0.46931(13) 0.21428(10) 0.45078(10) 0.0223(3) Uani 1 1 d . . . . .
H21 H 0.418878 0.152204 0.450766 0.027 Uiso 1 1 calc R U . . .
C22 C 0.54603(13) 0.23584(10) 0.37198(9) 0.0191(3) Uani 1 1 d . . . . .
H22 H 0.546440 0.188612 0.318232 0.023 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'
F F 0.0171 0.0103 '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
C1 O2 C9 121.41(9) . . ?
O1 C1 O2 116.84(11) . . ?
O1 C1 C2 124.61(11) . . ?
O2 C1 C2 118.53(10) . . ?
C7 C2 C3 120.74(11) . . ?
C7 C2 C1 120.19(11) . . ?
C3 C2 C1 119.08(11) . . ?
C4 C3 C2 119.53(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.94(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.60(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.97(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 119.21(11) . . ?
C6 C7 C8 120.93(11) . . ?
C2 C7 C8 119.81(10) . . ?
C7 C8 C10 110.03(9) . . ?
C7 C8 C9 110.54(9) . . ?
C10 C8 C9 112.45(9) . . ?
C7 C8 H8 107.9 . . ?
C10 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
O2 C9 C12 107.61(9) . . ?
O2 C9 C8 111.73(9) . . ?
C12 C9 C8 112.23(9) . . ?
O2 C9 C11 104.76(9) . . ?
C12 C9 C11 107.08(9) . . ?
C8 C9 C11 112.99(9) . . ?
C18 C10 C22 118.17(11) . . ?
C18 C10 C8 121.51(11) . . ?
C22 C10 C8 120.31(11) . . ?
F2 C11 F3 107.92(10) . . ?
F2 C11 F1 106.30(10) . . ?
F3 C11 F1 106.61(10) . . ?
F2 C11 C9 110.82(10) . . ?
F3 C11 C9 111.71(10) . . ?
F1 C11 C9 113.16(10) . . ?
C13 C12 C17 119.42(11) . . ?
C13 C12 C9 121.24(11) . . ?
C17 C12 C9 119.31(11) . . ?
C12 C13 C14 120.06(12) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.33(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.71(12) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.39(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.07(12) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C19 C18 C10 120.89(12) . . ?
C19 C18 H18 119.6 . . ?
C10 C18 H18 119.6 . . ?
C20 C19 C18 120.48(12) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.16(12) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.42(12) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C10 C22 C21 120.85(12) . . ?
C10 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
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
F1 C11 1.3448(14) . ?
F2 C11 1.3311(14) . ?
F3 C11 1.3341(14) . ?
O1 C1 1.2030(15) . ?
O2 C1 1.3694(14) . ?
O2 C9 1.4443(13) . ?
C1 C2 1.4770(16) . ?
C2 C7 1.3930(16) . ?
C2 C3 1.3973(17) . ?
C3 C4 1.3817(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3900(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3879(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3912(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.5122(16) . ?
C8 C10 1.5290(16) . ?
C8 C9 1.5448(16) . ?
C8 H8 1.0000 . ?
C9 C12 1.5244(16) . ?
C9 C11 1.5485(16) . ?
C10 C18 1.3917(17) . ?
C10 C22 1.3919(17) . ?
C12 C13 1.3900(17) . ?
C12 C17 1.3934(17) . ?
C13 C14 1.3911(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3878(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3879(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3861(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3813(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.3923(18) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
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
C9 O2 C1 O1 169.68(10) . . . . ?
C9 O2 C1 C2 -11.85(15) . . . . ?
O1 C1 C2 C7 168.99(12) . . . . ?
O2 C1 C2 C7 -9.35(17) . . . . ?
O1 C1 C2 C3 -10.68(18) . . . . ?
O2 C1 C2 C3 170.98(10) . . . . ?
C7 C2 C3 C4 0.70(18) . . . . ?
C1 C2 C3 C4 -179.63(11) . . . . ?
C2 C3 C4 C5 -1.14(19) . . . . ?
C3 C4 C5 C6 0.45(19) . . . . ?
C4 C5 C6 C7 0.71(19) . . . . ?
C5 C6 C7 C2 -1.13(18) . . . . ?
C5 C6 C7 C8 -178.53(11) . . . . ?
C3 C2 C7 C6 0.43(18) . . . . ?
C1 C2 C7 C6 -179.23(11) . . . . ?
C3 C2 C7 C8 177.86(10) . . . . ?
C1 C2 C7 C8 -1.80(17) . . . . ?
C6 C7 C8 C10 82.54(13) . . . . ?
C2 C7 C8 C10 -94.84(13) . . . . ?
C6 C7 C8 C9 -152.66(11) . . . . ?
C2 C7 C8 C9 29.95(14) . . . . ?
C1 O2 C9 C12 164.46(9) . . . . ?
C1 O2 C9 C8 40.84(13) . . . . ?
C1 O2 C9 C11 -81.82(12) . . . . ?
C7 C8 C9 O2 -47.61(12) . . . . ?
C10 C8 C9 O2 75.79(12) . . . . ?
C7 C8 C9 C12 -168.58(9) . . . . ?
C10 C8 C9 C12 -45.18(13) . . . . ?
C7 C8 C9 C11 70.22(12) . . . . ?
C10 C8 C9 C11 -166.37(9) . . . . ?
C7 C8 C10 C18 56.47(14) . . . . ?
C9 C8 C10 C18 -67.22(14) . . . . ?
C7 C8 C10 C22 -122.87(12) . . . . ?
C9 C8 C10 C22 113.45(12) . . . . ?
O2 C9 C11 F2 -62.47(12) . . . . ?
C12 C9 C11 F2 51.63(12) . . . . ?
C8 C9 C11 F2 175.69(9) . . . . ?
O2 C9 C11 F3 177.16(9) . . . . ?
C12 C9 C11 F3 -68.75(12) . . . . ?
C8 C9 C11 F3 55.32(13) . . . . ?
O2 C9 C11 F1 56.83(12) . . . . ?
C12 C9 C11 F1 170.92(10) . . . . ?
C8 C9 C11 F1 -65.01(13) . . . . ?
O2 C9 C12 C13 7.22(15) . . . . ?
C8 C9 C12 C13 130.54(11) . . . . ?
C11 C9 C12 C13 -104.93(12) . . . . ?
O2 C9 C12 C17 -174.86(10) . . . . ?
C8 C9 C12 C17 -51.55(14) . . . . ?
C11 C9 C12 C17 72.98(13) . . . . ?
C17 C12 C13 C14 1.61(18) . . . . ?
C9 C12 C13 C14 179.52(11) . . . . ?
C12 C13 C14 C15 -1.24(19) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C12 -0.4(2) . . . . ?
C13 C12 C17 C16 -0.77(18) . . . . ?
C9 C12 C17 C16 -178.72(11) . . . . ?
C22 C10 C18 C19 -1.99(18) . . . . ?
C8 C10 C18 C19 178.66(11) . . . . ?
C10 C18 C19 C20 1.23(19) . . . . ?
C18 C19 C20 C21 0.58(19) . . . . ?
C19 C20 C21 C22 -1.57(19) . . . . ?
C18 C10 C22 C21 0.98(18) . . . . ?
C8 C10 C22 C21 -179.66(11) . . . . ?
C20 C21 C22 C10 0.8(2) . . . . ?
