# Electronic Supplementary Material (ESI) for ChemComm.
# 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).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_gv_ak_239rf_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2256925'
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ganesh.v@chem.iitkgp.ac.in
aankhikhamrai@kgpian.iitkgp.ac.in
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-3-(2-(hydroxy(phenyl)methyl)hex-1-en-1-yl)oxazolidin-2-one
_chemical_formula_moiety         'C16 H21 N O3'
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34
_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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.4074(2)
_cell_length_b                   8.1039(2)
_cell_length_c                   31.1224(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2877.09(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.21
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1501 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8150.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1184
_exptl_crystal_preparation       DESILYLATION
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            57596
_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         27.121
_diffrn_reflns_theta_min         2.618
_diffrn_ambient_temperature      119.90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2935
_reflns_number_total             3176
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.086
_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)+(0.0450P)²+1.1446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C11(H11A,H11B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.20250(7) 0.21706(11) 0.51420(3) 0.0254(2) Uani 1 1 d . . . . .
O2 O 0.08931(7) 0.34798(10) 0.46564(3) 0.02391(19) Uani 1 1 d . . . . .
O3 O 0.45064(7) 0.77236(10) 0.37571(3) 0.0245(2) Uani 1 1 d . . . . .
H3 H 0.446654 0.809071 0.400911 0.037 Uiso 1 1 calc R U . . .
N1 N 0.29124(8) 0.35275(11) 0.46128(3) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.70715(11) 0.23855(17) 0.35365(5) 0.0321(3) Uani 1 1 d . . . . .
H1A H 0.681297 0.263665 0.324346 0.048 Uiso 1 1 calc R U . . .
H1B H 0.775952 0.166245 0.352575 0.048 Uiso 1 1 calc R U . . .
H1C H 0.727618 0.341288 0.368474 0.048 Uiso 1 1 calc R U . . .
C2 C 0.60882(10) 0.15242(14) 0.37779(4) 0.0223(2) Uani 1 1 d . . . . .
H2A H 0.633542 0.135306 0.407959 0.027 Uiso 1 1 calc R U . . .
H2B H 0.595751 0.042425 0.364807 0.027 Uiso 1 1 calc R U . . .
C3 C 0.49322(9) 0.24788(14) 0.37746(4) 0.0201(2) Uani 1 1 d . . . . .
H3A H 0.432755 0.181813 0.392452 0.024 Uiso 1 1 calc R U . . .
H3B H 0.467421 0.262683 0.347336 0.024 Uiso 1 1 calc R U . . .
C4 C 0.50189(9) 0.41838(13) 0.39908(3) 0.0182(2) Uani 1 1 d . . . . .
H4A H 0.533726 0.404715 0.428456 0.022 Uiso 1 1 calc R U . . .
H4B H 0.557372 0.487981 0.382652 0.022 Uiso 1 1 calc R U . . .
C5 C 0.38474(9) 0.50542(12) 0.40168(3) 0.0170(2) Uani 1 1 d . . . . .
C6 C 0.36465(9) 0.64579(13) 0.36998(3) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.285452 0.694178 0.375534 0.022 Uiso 1 1 calc R U . . .
C7 C 0.36881(9) 0.58632(13) 0.32380(3) 0.0192(2) Uani 1 1 d . . . . .
C8 C 0.46186(10) 0.62304(15) 0.29660(4) 0.0257(3) Uani 1 1 d . . . . .
H8 H 0.526147 0.686197 0.306893 0.031 Uiso 1 1 calc R U . . .
C9 C 0.46097(11) 0.56727(17) 0.25418(4) 0.0315(3) Uani 1 1 d . . . . .
H9 H 0.524274 0.593473 0.235553 0.038 Uiso 1 1 calc R U . . .
C10 C 0.36800(12) 0.47383(16) 0.23919(4) 0.0307(3) Uani 1 1 d . . . . .
H10 H 0.367460 0.436363 0.210270 0.037 Uiso 1 1 calc R U . . .
C11 C 0.32677(10) 0.21132(15) 0.52469(4) 0.0244(2) Uani 1 1 d . . . . .
H11A H 0.352890 0.095877 0.528773 0.029 Uiso 1 1 calc R U . . .
H11B H 0.342857 0.273983 0.551355 0.029 Uiso 1 1 calc R U . . .
C12 C 0.18637(10) 0.31061(13) 0.47868(3) 0.0196(2) Uani 1 1 d . . . . .
C13 C 0.29567(9) 0.47019(12) 0.42784(3) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.226067 0.532250 0.423385 0.020 Uiso 1 1 calc R U . . .
C14 C 0.27552(12) 0.43474(16) 0.26635(4) 0.0294(3) Uani 1 1 d . . . . .
H14 H 0.212202 0.369390 0.256174 0.035 Uiso 1 1 calc R U . . .
C15 C 0.27596(10) 0.49143(14) 0.30834(4) 0.0240(2) Uani 1 1 d . . . . .
H15 H 0.212287 0.465373 0.326807 0.029 Uiso 1 1 calc R U . . .
C16 C 0.38967(9) 0.28990(14) 0.48643(3) 0.0210(2) Uani 1 1 d . . . . .
H16A H 0.442380 0.380172 0.495702 0.025 Uiso 1 1 calc R U . . .
H16B H 0.435376 0.207194 0.470072 0.025 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
O1 C11 1.4554(14) . ?
O1 C12 1.3531(14) . ?
O2 C12 1.2175(14) . ?
O3 H3 0.8400 . ?
O3 C6 1.4304(13) . ?
N1 C12 1.3569(14) . ?
N1 C13 1.4113(13) . ?
N1 C16 1.4603(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5198(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5289(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5399(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5133(14) . ?
C5 C6 1.5231(14) . ?
C5 C13 1.3328(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5164(15) . ?
C7 C8 1.3901(15) . ?
C7 C15 1.3946(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3955(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3841(19) . ?
C10 H10 0.9500 . ?
C10 C14 1.3883(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C16 1.5293(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3852(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C12 O1 C11 109.49(8) . . ?
C6 O3 H3 109.5 . . ?
C12 N1 C13 119.71(9) . . ?
C12 N1 C16 112.10(9) . . ?
C13 N1 C16 127.08(9) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.63(10) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.31(9) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.64(9) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 C6 116.50(9) . . ?
C13 C5 C4 127.30(10) . . ?
C13 C5 C6 116.16(9) . . ?
O3 C6 C5 110.59(9) . . ?
O3 C6 H6 108.5 . . ?
O3 C6 C7 108.95(8) . . ?
C5 C6 H6 108.5 . . ?
C7 C6 C5 111.83(9) . . ?
C7 C6 H6 108.5 . . ?
C8 C7 C6 122.22(10) . . ?
C8 C7 C15 119.19(11) . . ?
C15 C7 C6 118.59(10) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.10(11) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.10(11) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C14 120.13(11) . . ?
C14 C10 H10 119.9 . . ?
O1 C11 H11A 110.6 . . ?
O1 C11 H11B 110.6 . . ?
O1 C11 C16 105.60(9) . . ?
H11A C11 H11B 108.8 . . ?
C16 C11 H11A 110.6 . . ?
C16 C11 H11B 110.6 . . ?
O1 C12 N1 110.31(9) . . ?
O2 C12 O1 122.37(10) . . ?
O2 C12 N1 127.31(10) . . ?
N1 C13 H13 115.8 . . ?
C5 C13 N1 128.47(10) . . ?
C5 C13 H13 115.8 . . ?
C10 C14 H14 120.1 . . ?
C15 C14 C10 119.73(12) . . ?
C15 C14 H14 120.1 . . ?
C7 C15 H15 119.6 . . ?
C14 C15 C7 120.74(11) . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C11 101.65(9) . . ?
N1 C16 H16A 111.4 . . ?
N1 C16 H16B 111.4 . . ?
C11 C16 H16A 111.4 . . ?
C11 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?

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
O1 C11 C16 N1 7.83(11) . . . . ?
O3 C6 C7 C8 14.64(14) . . . . ?
O3 C6 C7 C15 -165.46(9) . . . . ?
C1 C2 C3 C4 -61.45(13) . . . . ?
C2 C3 C4 C5 -175.38(9) . . . . ?
C3 C4 C5 C6 -104.42(11) . . . . ?
C3 C4 C5 C13 73.57(14) . . . . ?
C4 C5 C6 O3 -59.79(12) . . . . ?
C4 C5 C6 C7 61.81(12) . . . . ?
C4 C5 C13 N1 5.05(18) . . . . ?
C5 C6 C7 C8 -107.90(12) . . . . ?
C5 C6 C7 C15 72.00(12) . . . . ?
C6 C5 C13 N1 -176.96(10) . . . . ?
C6 C7 C8 C9 -179.17(11) . . . . ?
C6 C7 C15 C14 179.76(10) . . . . ?
C7 C8 C9 C10 -0.65(19) . . . . ?
C8 C7 C15 C14 -0.34(17) . . . . ?
C8 C9 C10 C14 -0.24(19) . . . . ?
C9 C10 C14 C15 0.83(19) . . . . ?
C10 C14 C15 C7 -0.54(18) . . . . ?
C11 O1 C12 O2 -172.75(10) . . . . ?
C11 O1 C12 N1 7.22(12) . . . . ?
C12 O1 C11 C16 -9.48(12) . . . . ?
C12 N1 C13 C5 -166.59(11) . . . . ?
C12 N1 C16 C11 -4.02(12) . . . . ?
C13 N1 C12 O1 -170.56(9) . . . . ?
C13 N1 C12 O2 9.41(17) . . . . ?
C13 N1 C16 C11 163.77(10) . . . . ?
C13 C5 C6 O3 121.99(10) . . . . ?
C13 C5 C6 C7 -116.41(11) . . . . ?
C15 C7 C8 C9 0.93(17) . . . . ?
C16 N1 C12 O1 -1.76(12) . . . . ?
C16 N1 C12 O2 178.22(11) . . . . ?
C16 N1 C13 C5 26.45(18) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id gv_ak_239RF
_olex2_submission_special_instructions 'No special instructions were received'
