# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ic21443
_audit_block_doi                 10.5517/ccdc.csd.cc2fbh5g
_database_code_depnum_ccdc_archive 'CCDC 2244405'
loop_
_audit_author_name
_audit_author_address
'Hsiu-Hui Chen'
;National Taipei University of Technology
Taiwan
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
(Z)-5-benzylidene-4-(4-methoxyphenyl)-3-(4-(trifluoromethyl)benzyl)oxazolidin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 F3 N O3'
_chemical_formula_weight         439.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.0518(4)
_cell_length_b                   10.0983(2)
_cell_length_c                   10.6704(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.6280(10)
_cell_angle_gamma                90
_cell_volume                     2090.60(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5351
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_T_max  0.9604
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31962
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6096
_reflns_number_gt                4076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.7504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6096
_refine_ls_number_parameters     311
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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) . ?

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) . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
