# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
# 
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data_200825_dll_a_6_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2054232'
loop_
_audit_author_name
_audit_author_address
'Dai Linlong'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(R)-3-(5-(4-chlorophenyl)-3-phenylimidazolidin-1-yl)oxazolidin-2-one
_chemical_formula_moiety         'C18 H18 Cl N3 O2'
_chemical_formula_sum            'C18 H18 Cl N3 O2'
_chemical_formula_weight         343.80
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0897(15)
_cell_length_b                   9.406(2)
_cell_length_c                   28.473(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1631.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1086 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.9422.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            20803
_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         27.068
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3500
_reflns_number_total             3592
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       SAINT
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.2433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.39517(11) -0.09108(5) 0.51034(2) 0.04912(16) Uani 1 1 d . . . . .
O1 O 0.33067(19) 0.21002(12) 0.71852(4) 0.0276(2) Uani 1 1 d . . . . .
O2 O -0.02530(18) 0.25194(13) 0.73501(4) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.4771(2) 0.66762(14) 0.63480(4) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.3213(2) 0.46525(13) 0.66459(4) 0.0191(2) Uani 1 1 d . . . . .
N3 N 0.1472(2) 0.41119(14) 0.69150(4) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.8189(3) 0.76791(17) 0.60576(6) 0.0272(3) Uani 1 1 d . . . . .
H1 H 0.820673 0.701975 0.580486 0.033 Uiso 1 1 calc R . . . .
C2 C 0.9883(3) 0.86618(19) 0.61046(7) 0.0356(4) Uani 1 1 d . . . . .
H2 H 1.106539 0.865259 0.588700 0.043 Uiso 1 1 calc R . . . .
C3 C 0.9869(3) 0.9655(2) 0.64651(7) 0.0377(4) Uani 1 1 d . . . . .
H3 H 1.102991 1.032277 0.649576 0.045 Uiso 1 1 calc R . . . .
C4 C 0.8130(3) 0.96557(19) 0.67799(6) 0.0336(4) Uani 1 1 d . . . . .
H4 H 0.809671 1.034002 0.702516 0.040 Uiso 1 1 calc R . . . .
C5 C 0.6442(3) 0.86768(16) 0.67426(5) 0.0263(3) Uani 1 1 d . . . . .
H5 H 0.526772 0.869252 0.696224 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6459(2) 0.76581(15) 0.63807(5) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.3645(3) 0.61591(15) 0.67659(5) 0.0224(3) Uani 1 1 d . . . . .
H7A H 0.226036 0.668492 0.682073 0.027 Uiso 1 1 calc R . . . .
H7B H 0.458918 0.623944 0.704767 0.027 Uiso 1 1 calc R . . . .
C8 C 0.2821(2) 0.46418(16) 0.61308(5) 0.0204(3) Uani 1 1 d . . . . .
H8 H 0.136069 0.507563 0.605825 0.024 Uiso 1 1 calc R . . . .
C9 C 0.4668(3) 0.56312(16) 0.59710(5) 0.0230(3) Uani 1 1 d . . . . .
H9A H 0.607329 0.511084 0.594020 0.028 Uiso 1 1 calc R . . . .
H9B H 0.430880 0.608691 0.566711 0.028 Uiso 1 1 calc R . . . .
C10 C 0.1707(2) 0.28494(16) 0.71483(5) 0.0214(3) Uani 1 1 d . . . . .
C11 C -0.1789(3) 0.36897(19) 0.72798(6) 0.0303(4) Uani 1 1 d . . . . .
H11A H -0.192052 0.426984 0.756852 0.036 Uiso 1 1 calc R . . . .
H11B H -0.326121 0.332595 0.719395 0.036 Uiso 1 1 calc R . . . .
C12 C -0.0822(2) 0.45617(19) 0.68815(6) 0.0277(3) Uani 1 1 d . . . . .
H12A H -0.147652 0.430741 0.657456 0.033 Uiso 1 1 calc R . . . .
H12B H -0.098955 0.559526 0.693642 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2987(3) 0.31830(15) 0.59107(5) 0.0208(3) Uani 1 1 d . . . . .
C14 C 0.1519(3) 0.27957(18) 0.55578(6) 0.0300(3) Uani 1 1 d . . . . .
H14 H 0.031613 0.340075 0.548553 0.036 Uiso 1 1 calc R . . . .
C15 C 0.1794(4) 0.1529(2) 0.53092(6) 0.0355(4) Uani 1 1 d . . . . .
H15 H 0.079147 0.126613 0.506878 0.043 Uiso 1 1 calc R . . . .
C16 C 0.3549(3) 0.06676(16) 0.54198(5) 0.0309(4) Uani 1 1 d . . . . .
C17 C 0.4999(3) 0.09997(18) 0.57760(6) 0.0300(4) Uani 1 1 d . . . . .
H17 H 0.617737 0.037875 0.585185 0.036 Uiso 1 1 calc R . . . .
C18 C 0.4698(3) 0.22644(17) 0.60218(5) 0.0251(3) Uani 1 1 d . . . . .
H18 H 0.567629 0.250311 0.626937 0.030 Uiso 1 1 calc R . . . .


_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
Cl1 C16 1.7539(16) . ?
O1 C10 1.207(2) . ?
O2 C10 1.3608(18) . ?
O2 C11 1.459(2) . ?
N1 C6 1.3849(19) . ?
N1 C7 1.4570(18) . ?
N1 C9 1.4568(19) . ?
N2 N3 1.4033(17) . ?
N2 C7 1.4813(19) . ?
N2 C8 1.4859(17) . ?
N3 C10 1.3682(19) . ?
N3 C12 1.4628(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(2) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.407(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C9 1.529(2) . ?
C8 C13 1.512(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.394(2) . ?
C13 C18 1.390(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(2) . ?
C18 H18 0.9500 . ?

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
C10 O2 C11 109.43(12) . . ?
C6 N1 C7 121.13(12) . . ?
C6 N1 C9 122.12(12) . . ?
C9 N1 C7 110.86(12) . . ?
N3 N2 C7 110.79(11) . . ?
N3 N2 C8 114.53(12) . . ?
C7 N2 C8 105.22(11) . . ?
N2 N3 C12 125.52(12) . . ?
C10 N3 N2 120.04(12) . . ?
C10 N3 C12 112.49(12) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.29(16) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.90(17) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.88(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.13(17) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.24(15) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C1 121.60(14) . . ?
N1 C6 C5 119.86(13) . . ?
C1 C6 C5 118.54(14) . . ?
N1 C7 N2 102.40(11) . . ?
N1 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
N2 C7 H7A 111.3 . . ?
N2 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N2 C8 H8 110.1 . . ?
N2 C8 C9 99.87(11) . . ?
N2 C8 C13 113.86(12) . . ?
C9 C8 H8 110.1 . . ?
C13 C8 H8 110.1 . . ?
C13 C8 C9 112.32(12) . . ?
N1 C9 C8 102.90(12) . . ?
N1 C9 H9A 111.2 . . ?
N1 C9 H9B 111.2 . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
O1 C10 O2 122.55(14) . . ?
O1 C10 N3 129.32(14) . . ?
O2 C10 N3 108.13(13) . . ?
O2 C11 H11A 110.7 . . ?
O2 C11 H11B 110.7 . . ?
O2 C11 C12 105.14(13) . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
N3 C12 C11 99.54(13) . . ?
N3 C12 H12A 111.9 . . ?
N3 C12 H12B 111.9 . . ?
C11 C12 H12A 111.9 . . ?
C11 C12 H12B 111.9 . . ?
H12A C12 H12B 109.6 . . ?
C14 C13 C8 119.55(14) . . ?
C18 C13 C8 121.33(13) . . ?
C18 C13 C14 118.85(14) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.77(16) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.64(16) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 Cl1 119.26(14) . . ?
C15 C16 C17 122.07(15) . . ?
C17 C16 Cl1 118.66(15) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.57(16) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 121.04(15) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
