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#$Date: 2023-08-05 12:31:58 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159414.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_7159414
loop_
_publ_author_name
'Egashira, Mayumi'
'Chen, Hsiu-Hui'
_publ_section_title
;
 Highly efficient fixation of carbon dioxide into 2-oxazolidinones under
 mild conditions by using a reusable ionic liquid/CuI catalyst system.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5377
_journal_page_last               5381
_journal_paper_doi               10.1039/d3ob00698k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C25 H20 F3 N O3'
_chemical_formula_weight         439.42
_chemical_name_systematic
(Z)-5-benzylidene-4-(4-methoxyphenyl)-3-(4-(trifluoromethyl)benzyl)oxazolidin-2-one
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2fbh5g
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0518(4)
_cell_length_b                   10.0983(2)
_cell_length_c                   10.6704(3)
_cell_measurement_reflns_used    5351
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.83
_cell_volume                     2090.60(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         2.822
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.046
_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     311
_refine_ls_number_reflns         6096
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0689P)²+0.7504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4076
_reflns_number_total             6096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00698k2.cif
_cod_data_source_block           ic21443
_cod_depositor_comments          'Adding full bibliography for 7159414.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159414
_shelx_shelxl_version_number     2019/1
_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   0.975
_shelx_estimated_absorpt_t_max   0.988
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
F1 F 0.5583(2) 0.4253(5) 0.2959(4) 0.0630(10) Uani 0.502(2) 1 d D U P A 1
F2 F 0.5925(5) 0.6181(13) 0.2712(12) 0.0828(14) Uani 0.502(2) 1 d D U P A 1
F3 F 0.51977(17) 0.5858(5) 0.3916(3) 0.0702(9) Uani 0.502(2) 1 d D U P A 1
F1' F 0.5431(4) 0.4343(8) 0.3294(8) 0.0630(10) Uani 0.310(3) 1 d D . P A 2
F2' F 0.5930(9) 0.594(2) 0.251(2) 0.0828(14) Uani 0.310(3) 1 d D . P A 2
F3' F 0.5319(3) 0.6502(6) 0.3718(5) 0.0702(9) Uani 0.310(3) 1 d D . P A 2
F1" F 0.5774(5) 0.4615(9) 0.2831(12) 0.0630(10) Uani 0.188(2) 1 d D . P A 3
F2" F 0.5674(4) 0.6658(8) 0.3266(10) 0.0828(14) Uani 0.188(2) 1 d D . P A 3
F3" F 0.5118(4) 0.5104(10) 0.3921(7) 0.0702(9) Uani 0.188(2) 1 d D . P A 3
O1 O 0.14316(6) 0.61893(11) -0.05015(12) 0.0377(3) Uani 1 1 d . . . . .
O2 O 0.18125(7) 0.44802(12) -0.14909(14) 0.0482(3) Uani 1 1 d . . . . .
O3 O 0.27150(8) 1.24410(14) -0.29504(16) 0.0590(4) Uani 1 1 d . . . . .
N1 N 0.23853(7) 0.64771(14) -0.11567(14) 0.0366(3) Uani 1 1 d . . . . .
C1 C 0.18880(8) 0.55997(17) -0.11029(17) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.23465(8) 0.76808(16) -0.04170(16) 0.0342(3) Uani 1 1 d . . . . .
H2 H 0.271251 0.764561 0.041569 0.041 Uiso 1 1 calc R U . . .
C3 C 0.16498(8) 0.74718(16) -0.01316(16) 0.0334(3) Uani 1 1 d . . . . .
C4 C 0.29963(8) 0.61103(19) -0.15733(18) 0.0413(4) Uani 1 1 d . . . . .
H4A H 0.309251 0.680141 -0.216201 0.050 Uiso 1 1 calc R U . . .
H4B H 0.290833 0.526873 -0.206335 0.050 Uiso 1 1 calc R U . . .
C5 C 0.36205(8) 0.59466(17) -0.04423(18) 0.0390(4) Uani 1 1 d . . . . .
C6 C 0.36256(10) 0.4993(2) 0.0484(2) 0.0589(6) Uani 1 1 d . . . . .
H6 H 0.324028 0.442113 0.039457 0.071 Uiso 1 1 calc R U . . .
C7 C 0.41861(10) 0.4859(3) 0.1543(2) 0.0646(7) Uani 1 1 d . . . . .
H7 H 0.418241 0.420931 0.218488 0.078 Uiso 1 1 calc R U . . .
C8 C 0.47530(9) 0.5680(2) 0.1660(2) 0.0479(5) Uani 1 1 d . . . . .
C9 C 0.47583(10) 0.6606(2) 0.0729(2) 0.0516(5) Uani 1 1 d . . . . .
H9 H 0.515082 0.715452 0.079798 0.062 Uiso 1 1 calc R U . . .
C10 C 0.41905(9) 0.67427(18) -0.0318(2) 0.0458(4) Uani 1 1 d . . . . .
H10 H 0.419481 0.739458 -0.095767 0.055 Uiso 1 1 calc R U . . .
C11 C 0.53478(11) 0.5555(2) 0.2825(2) 0.0614(6) Uani 1 1 d D . . . .
C12 C 0.24283(8) 0.89393(16) -0.11151(16) 0.0342(3) Uani 1 1 d . . . . .
C13 C 0.30191(9) 0.97100(19) -0.06963(19) 0.0438(4) Uani 1 1 d . . . . .
H13 H 0.337221 0.943074 0.002854 0.053 Uiso 1 1 calc R U . . .
C14 C 0.30977(10) 1.0874(2) -0.1321(2) 0.0498(5) Uani 1 1 d . . . . .
H14 H 0.350151 1.139296 -0.101994 0.060 Uiso 1 1 calc R U . . .
C15 C 0.25898(10) 1.12887(17) -0.23875(19) 0.0438(4) Uani 1 1 d . . . . .
C16 C 0.20012(9) 1.05254(17) -0.28253(18) 0.0403(4) Uani 1 1 d . . . . .
H16 H 0.165179 1.079923 -0.355851 0.048 Uiso 1 1 calc R U . . .
C17 C 0.19264(8) 0.93619(16) -0.21865(17) 0.0373(4) Uani 1 1 d . . . . .
H17 H 0.152258 0.884292 -0.248915 0.045 Uiso 1 1 calc R U . . .
C18 C 0.21747(14) 1.2935(2) -0.3989(2) 0.0634(6) Uani 1 1 d . . . . .
H18A H 0.208169 1.229833 -0.470500 0.095 Uiso 1 1 calc R U . . .
H18B H 0.231523 1.378328 -0.428743 0.095 Uiso 1 1 calc R U . . .
H18C H 0.175690 1.306173 -0.368499 0.095 Uiso 1 1 calc R U . . .
C19 C 0.12916(8) 0.83118(16) 0.03945(17) 0.0365(4) Uani 1 1 d . . . . .
H19 H 0.149123 0.916627 0.057342 0.044 Uiso 1 1 calc R U . . .
C20 C 0.06354(8) 0.81315(16) 0.07447(16) 0.0343(3) Uani 1 1 d . . . . .
C21 C 0.03979(9) 0.91611(18) 0.13825(19) 0.0423(4) Uani 1 1 d . . . . .
H21 H 0.065688 0.995765 0.155762 0.051 Uiso 1 1 calc R U . . .
C22 C -0.02104(10) 0.9045(2) 0.1767(2) 0.0512(5) Uani 1 1 d . . . . .
H22 H -0.036679 0.976181 0.219369 0.061 Uiso 1 1 calc R U . . .
C23 C -0.05870(9) 0.7896(2) 0.1532(2) 0.0508(5) Uani 1 1 d . . . . .
H23 H -0.100001 0.780895 0.180742 0.061 Uiso 1 1 calc R U . . .
C24 C -0.03617(10) 0.6871(2) 0.0895(2) 0.0518(5) Uani 1 1 d . . . . .
H24 H -0.062352 0.607699 0.072699 0.062 Uiso 1 1 calc R U . . .
C25 C 0.02409(9) 0.69795(18) 0.0496(2) 0.0448(4) Uani 1 1 d . . . . .
H25 H 0.038668 0.626536 0.004987 0.054 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'
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
C1 O1 C3 109.62(12) . . ?
C15 O3 C18 116.87(16) . . ?
C1 N1 C4 122.43(14) . . ?
C1 N1 C2 112.53(13) . . ?
C4 N1 C2 122.76(13) . . ?
O2 C1 N1 129.46(16) . . ?
O2 C1 O1 121.78(15) . . ?
N1 C1 O1 108.76(14) . . ?
N1 C2 C12 114.09(13) . . ?
N1 C2 C3 99.78(12) . . ?
C12 C2 C3 115.99(13) . . ?
C19 C3 O1 123.43(14) . . ?
C19 C3 C2 128.39(15) . . ?
O1 C3 C2 108.17(13) . . ?
N1 C4 C5 112.05(14) . . ?
C10 C5 C6 118.91(17) . . ?
C10 C5 C4 120.86(17) . . ?
C6 C5 C4 120.23(16) . . ?
C5 C6 C7 120.74(19) . . ?
C6 C7 C8 119.6(2) . . ?
C9 C8 C7 119.99(19) . . ?
C9 C8 C11 120.79(19) . . ?
C7 C8 C11 119.2(2) . . ?
C8 C9 C10 119.92(18) . . ?
C5 C10 C9 120.86(18) . . ?
F1" C11 F2" 110.8(6) . . ?
F3 C11 F2 111.4(4) . . ?
F1' C11 F2' 109.3(13) . . ?
F1' C11 F3' 114.2(5) . . ?
F2' C11 F3' 99.3(7) . . ?
F3 C11 F1 106.1(3) . . ?
F2 C11 F1 100.1(7) . . ?
F1" C11 F3" 96.5(6) . . ?
F2" C11 F3" 102.1(6) . . ?
F1" C11 C8 117.4(6) . . ?
F3 C11 C8 113.9(2) . . ?
F1' C11 C8 113.1(5) . . ?
F2" C11 C8 116.4(4) . . ?
F2 C11 C8 114.0(7) . . ?
F2' C11 C8 109.1(12) . . ?
F3' C11 C8 110.8(3) . . ?
F1 C11 C8 110.1(3) . . ?
F3" C11 C8 110.6(4) . . ?
C17 C12 C13 118.29(16) . . ?
C17 C12 C2 121.45(14) . . ?
C13 C12 C2 120.25(15) . . ?
C14 C13 C12 120.82(18) . . ?
C13 C14 C15 120.28(16) . . ?
O3 C15 C14 116.18(17) . . ?
O3 C15 C16 124.19(19) . . ?
C14 C15 C16 119.63(17) . . ?
C17 C16 C15 119.59(17) . . ?
C16 C17 C12 121.38(15) . . ?
C3 C19 C20 130.21(15) . . ?
C21 C20 C25 117.97(15) . . ?
C21 C20 C19 118.14(15) . . ?
C25 C20 C19 123.88(15) . . ?
C22 C21 C20 121.11(17) . . ?
C23 C22 C21 120.16(18) . . ?
C22 C23 C24 119.46(17) . . ?
C23 C24 C25 120.91(18) . . ?
C24 C25 C20 120.37(17) . . ?
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 1.392(5) . ?
F2 C11 1.351(6) . ?
F3 C11 1.310(4) . ?
F1' C11 1.316(7) . ?
F2' C11 1.352(8) . ?
F3' C11 1.362(5) . ?
F1" C11 1.277(8) . ?
F2" C11 1.317(7) . ?
F3" C11 1.435(7) . ?
O1 C1 1.3787(19) . ?
O1 C3 1.3919(19) . ?
O2 C1 1.200(2) . ?
O3 C15 1.362(2) . ?
O3 C18 1.429(3) . ?
N1 C1 1.346(2) . ?
N1 C4 1.453(2) . ?
N1 C2 1.462(2) . ?
C2 C12 1.503(2) . ?
C2 C3 1.518(2) . ?
C3 C19 1.324(2) . ?
C4 C5 1.512(2) . ?
C5 C10 1.376(2) . ?
C5 C6 1.378(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.367(3) . ?
C8 C11 1.495(3) . ?
C9 C10 1.386(3) . ?
C12 C17 1.386(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.380(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.388(2) . ?
C16 C17 1.385(2) . ?
C19 C20 1.467(2) . ?
C20 C21 1.391(2) . ?
C20 C25 1.394(2) . ?
C21 C22 1.387(3) . ?
C22 C23 1.373(3) . ?
C23 C24 1.376(3) . ?
C24 C25 1.383(3) . ?
