# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_RST-463(S)
_database_code_depnum_ccdc_archive 'CCDC 1981280'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2020-02-01 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(S)-N-(2-(2-hydroxy-3-phenoxypropyl)phenyl)acetamide
_chemical_name_common            ?
_chemical_melting_point          390
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33

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'

_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'

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

_cell_length_a                   10.2060(4)
_cell_length_b                   11.8825(5)
_cell_length_c                   12.7337(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1544.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.16

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50079
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3821
_reflns_number_gt                3171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0577P)²+0.2713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1244 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ab
_refine_ls_number_reflns         3821
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.0818(3) -0.0491(2) 0.16453(19) 0.0469(6) Uani 1 1 d . . . . .
C2 C 0.0876(4) -0.1653(3) 0.1728(2) 0.0639(8) Uani 1 1 d . . . . .
H2 H 0.1509 -0.1993 0.2160 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0005(4) -0.2310(3) 0.1172(3) 0.0760(10) Uani 1 1 d . . . . .
H3 H 0.0031 -0.3098 0.1228 0.091 Uiso 1 1 calc R U . . .
C4 C -0.0934(4) -0.1812(3) 0.0537(2) 0.0739(10) Uani 1 1 d . . . . .
H4 H -0.1528 -0.2258 0.0155 0.089 Uiso 1 1 calc R U . . .
C5 C -0.0984(3) -0.0653(3) 0.0468(2) 0.0575(7) Uani 1 1 d . . . . .
H5 H -0.1624 -0.0319 0.0038 0.069 Uiso 1 1 calc R U . . .
C6 C -0.0118(2) 0.0035(2) 0.10136(18) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.1743(2) 0.0191(2) 0.21929(16) 0.0469(5) Uani 1 1 d . . . . .
H1 H 0.208(3) 0.073(3) 0.185(2) 0.054(8) Uiso 1 1 d . . . . .
C7 C 0.2133(2) 0.0052(2) 0.31900(19) 0.0457(5) Uani 1 1 d . . . . .
C8 C 0.3166(3) 0.0843(2) 0.3556(2) 0.0536(6) Uani 1 1 d . . . . .
H8A H 0.3401 0.1349 0.2989 0.080 Uiso 1 1 calc R U . . .
H8B H 0.2838 0.1276 0.4146 0.080 Uiso 1 1 calc R U . . .
H8C H 0.3933 0.0421 0.3773 0.080 Uiso 1 1 calc R U . . .
O1 O 0.1657(2) -0.0682(2) 0.37565(15) 0.0615(6) Uani 1 1 d . . . . .
C9 C -0.0184(2) 0.1294(2) 0.08855(19) 0.0468(6) Uani 1 1 d . . . . .
H9A H 0.0023 0.1651 0.1559 0.056 Uiso 1 1 calc R U . . .
H9B H -0.1081 0.1508 0.0696 0.056 Uiso 1 1 calc R U . . .
C10 C 0.0756(2) 0.1736(2) 0.00493(17) 0.0389(5) Uani 1 1 d . . . . .
H10 H 0.060(3) 0.130(2) -0.059(2) 0.038(7) Uiso 1 1 d . . . . .
O2 O 0.20695(16) 0.15950(15) 0.04087(13) 0.0415(4) Uani 1 1 d . . . . .
H2A H 0.254(4) 0.136(3) -0.011(3) 0.075(11) Uiso 1 1 d . . . . .
C11 C 0.0482(2) 0.2947(2) -0.01965(19) 0.0452(6) Uani 1 1 d . . . . .
H11A H -0.0442 0.3047 -0.0383 0.054 Uiso 1 1 calc R U . . .
H11B H 0.0676 0.3419 0.0415 0.054 Uiso 1 1 calc R U . . .
O3 O 0.13027(18) 0.32564(15) -0.10617(15) 0.0510(4) Uani 1 1 d . . . . .
C12 C 0.1127(3) 0.4297(2) -0.1495(2) 0.0490(6) Uani 1 1 d . . . . .
C13 C 0.1915(3) 0.4532(3) -0.2359(2) 0.0616(8) Uani 1 1 d . . . . .
H13 H 0.2507 0.3988 -0.2608 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1827(5) 0.5561(3) -0.2849(3) 0.0826(12) Uani 1 1 d . . . . .
H14 H 0.2373 0.5725 -0.3424 0.099 Uiso 1 1 calc R U . . .
C15 C 0.0941(5) 0.6352(3) -0.2500(3) 0.0938(15) Uani 1 1 d . . . . .
H15 H 0.0872 0.7052 -0.2841 0.113 Uiso 1 1 calc R U . . .
C16 C 0.0168(5) 0.6115(3) -0.1662(3) 0.0892(14) Uani 1 1 d . . . . .
H16 H -0.0434 0.6660 -0.1429 0.107 Uiso 1 1 calc R U . . .
C17 C 0.0240(4) 0.5087(3) -0.1134(3) 0.0652(8) Uani 1 1 d . . . . .
H17 H -0.0298 0.4937 -0.0552 0.078 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
C1 C2 1.385(4) . ?
C1 C6 1.397(4) . ?
C1 N1 1.426(3) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9400 . ?
C6 C9 1.507(4) . ?
N1 C7 1.341(3) . ?
N1 H1 0.85(3) . ?
C7 O1 1.231(3) . ?
C7 C8 1.488(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C10 1.527(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 O2 1.427(3) 1 ?
C10 O2 1.427(3) . ?
C10 C11 1.499(3) . ?
C10 H10 0.98(3) . ?
O2 O2 0.000(5) 1 ?
O2 H2A 0.87(4) . ?
C11 O3 1.432(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
O3 C12 1.366(3) . ?
C12 C17 1.383(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.357(7) . ?
C15 H15 0.9400 . ?
C16 C17 1.396(5) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?

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
C2 C1 C6 121.3(3) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 118.7(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C9 120.1(3) . . ?
C1 C6 C9 122.5(2) . . ?
C7 N1 C1 126.1(2) . . ?
C7 N1 H1 117(2) . . ?
C1 N1 H1 117(2) . . ?
O1 C7 N1 121.7(3) . . ?
O1 C7 C8 122.9(2) . . ?
N1 C7 C8 115.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 C10 112.9(2) . . ?
C6 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C6 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O2 C10 C11 110.8(2) 1 . ?
O2 C10 C11 110.8(2) . . ?
O2 C10 C9 109.06(18) 1 . ?
O2 C10 C9 109.06(18) . . ?
C11 C10 C9 111.0(2) . . ?
O2 C10 H10 110.9(16) 1 . ?
O2 C10 H10 110.9(16) . . ?
C11 C10 H10 108.0(15) . . ?
C9 C10 H10 107.0(16) . . ?
C10 O2 H2A 108(2) . . ?
O3 C11 C10 107.35(19) . . ?
O3 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C12 O3 C11 117.8(2) . . ?
O3 C12 C17 124.5(3) . . ?
O3 C12 C13 115.2(3) . . ?
C17 C12 C13 120.3(3) . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 122.0(4) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C12 C17 C16 118.0(4) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?

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
C6 C1 C2 C3 0.4(4) . . . . ?
N1 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C9 178.1(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
N1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C9 -178.4(2) . . . . ?
N1 C1 C6 C9 0.3(3) . . . . ?
C2 C1 N1 C7 -44.0(4) . . . . ?
C6 C1 N1 C7 137.3(3) . . . . ?
C1 N1 C7 O1 -3.5(4) . . . . ?
C1 N1 C7 C8 176.8(2) . . . . ?
C5 C6 C9 C10 -94.2(3) . . . . ?
C1 C6 C9 C10 83.8(3) . . . . ?
C6 C9 C10 O2 -68.4(3) . . . 1 ?
C6 C9 C10 O2 -68.4(3) . . . . ?
C6 C9 C10 C11 169.2(2) . . . . ?
C11 C10 O2 O2 0.00(4) . . . 1 ?
C9 C10 O2 O2 0.00(2) . . . 1 ?
O2 C10 C11 O3 64.9(2) 1 . . . ?
O2 C10 C11 O3 64.9(2) . . . . ?
C9 C10 C11 O3 -173.76(19) . . . . ?
C10 C11 O3 C12 173.5(2) . . . . ?
C11 O3 C12 C17 2.3(4) . . . . ?
C11 O3 C12 C13 -177.5(2) . . . . ?
O3 C12 C13 C14 -179.3(3) . . . . ?
C17 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
O3 C12 C17 C16 -179.8(3) . . . . ?
C13 C12 C17 C16 -0.1(4) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.85(3) 2.10(3) 2.838(3) 144(3) 1
O2 H2A O1 0.87(4) 1.84(4) 2.701(3) 171(4) 2_554

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/Ethyl acetate'
