# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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. 
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data_181211_phenta_0m
_database_code_depnum_ccdc_archive 'CCDC 1979128'
loop_
_audit_author_name
_audit_author_address
'Tianwen Bai'
;Zhejiang University
China
;
_audit_update_record             
;
2020-01-21 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        DL-Phe-NTA
_chemical_formula_moiety         'C10 H9 N O2 S'
_chemical_formula_sum            'C10 H9 N O2 S'
_chemical_formula_weight         207.24
_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'
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'
S S 0.1246 0.1234 '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                   5.2044(2)
_cell_length_b                   14.8960(7)
_cell_length_c                   25.4784(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1975.21(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6425
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.8762.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14300
_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         26.751
_diffrn_reflns_theta_min         2.735
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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         0.708
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3737
_reflns_number_total             4192
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.167
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_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     253
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), N2(H2A), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_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
S1 S -0.30466(13) 0.77909(4) 0.28020(3) 0.05557(17) Uani 1 1 d . . . . .
O1 O -0.4520(4) 0.80954(14) 0.37748(8) 0.0717(5) Uani 1 1 d . . . . .
O2 O 0.0539(4) 0.68407(12) 0.23272(7) 0.0593(4) Uani 1 1 d . . . . .
N1 N 0.0597(4) 0.68559(13) 0.32232(7) 0.0480(4) Uani 1 1 d . . . . .
H1 H 0.191739 0.651264 0.325337 0.058 Uiso 1 1 calc R . . . .
C1 C 0.1382(7) 0.6329(2) 0.48397(11) 0.0694(8) Uani 1 1 d . . . . .
H1A H 0.056300 0.682105 0.498951 0.083 Uiso 1 1 calc R . . . .
C2 C 0.3368(8) 0.5920(2) 0.51034(13) 0.0849(10) Uani 1 1 d . . . . .
H2 H 0.388251 0.613900 0.542868 0.102 Uiso 1 1 calc R . . . .
C3 C 0.4586(7) 0.5198(3) 0.48921(16) 0.0872(11) Uani 1 1 d . . . . .
H3 H 0.593806 0.492693 0.507040 0.105 Uiso 1 1 calc R . . . .
C4 C 0.3811(7) 0.4873(2) 0.44158(15) 0.0799(10) Uani 1 1 d . . . . .
H4 H 0.463356 0.437751 0.427060 0.096 Uiso 1 1 calc R . . . .
C5 C 0.1810(6) 0.52783(16) 0.41496(11) 0.0632(7) Uani 1 1 d . . . . .
H5 H 0.128389 0.504813 0.382778 0.076 Uiso 1 1 calc R . . . .
C6 C 0.0587(5) 0.60179(16) 0.43545(10) 0.0528(6) Uani 1 1 d . . . . .
C7 C -0.1588(5) 0.64709(17) 0.40654(10) 0.0589(6) Uani 1 1 d . . . . .
H7A H -0.275571 0.673386 0.431912 0.071 Uiso 1 1 calc R . . . .
H7B H -0.253365 0.602228 0.386832 0.071 Uiso 1 1 calc R . . . .
C8 C -0.0672(5) 0.72038(16) 0.36887(9) 0.0485(5) Uani 1 1 d . . . . .
H8 H 0.051272 0.760358 0.387504 0.058 Uiso 1 1 calc R . . . .
C9 C -0.2964(5) 0.77485(16) 0.34947(10) 0.0521(5) Uani 1 1 d . . . . .
C10 C -0.0291(4) 0.70705(14) 0.27510(10) 0.0445(5) Uani 1 1 d . . . . .
S2 S 0.82153(14) 0.45451(4) 0.24745(3) 0.05761(17) Uani 1 1 d . . . . .
O3 O 0.9610(4) 0.43858(13) 0.14808(8) 0.0705(5) Uani 1 1 d . . . . .
O4 O 0.4826(4) 0.54988(13) 0.30110(7) 0.0641(5) Uani 1 1 d . . . . .
N2 N 0.4741(4) 0.56215(13) 0.21191(7) 0.0470(4) Uani 1 1 d . . . . .
H2A H 0.348354 0.599578 0.211186 0.056 Uiso 1 1 calc R . . . .
C11 C 0.3529(5) 0.65234(16) 0.06463(10) 0.0534(6) Uani 1 1 d . . . . .
H11 H 0.392288 0.600222 0.046218 0.064 Uiso 1 1 calc R . . . .
C12 C 0.1624(6) 0.70802(18) 0.04600(11) 0.0618(7) Uani 1 1 d . . . . .
H12 H 0.076911 0.693689 0.015060 0.074 Uiso 1 1 calc R . . . .
C13 C 0.0984(6) 0.78452(18) 0.07291(12) 0.0660(7) Uani 1 1 d . . . . .
H13 H -0.029950 0.822281 0.060367 0.079 Uiso 1 1 calc R . . . .
C14 C 0.2249(7) 0.80462(18) 0.11823(12) 0.0754(9) Uani 1 1 d . . . . .
H14 H 0.180172 0.855811 0.137019 0.090 Uiso 1 1 calc R . . . .
C15 C 0.4193(6) 0.74956(17) 0.13654(10) 0.0638(7) Uani 1 1 d . . . . .
H15 H 0.506087 0.764883 0.167164 0.077 Uiso 1 1 calc R . . . .
C16 C 0.4867(5) 0.67197(15) 0.10993(9) 0.0467(5) Uani 1 1 d . . . . .
C17 C 0.6942(5) 0.61091(16) 0.12987(9) 0.0514(5) Uani 1 1 d . . . . .
H17A H 0.814270 0.645763 0.150684 0.062 Uiso 1 1 calc R . . . .
H17B H 0.787585 0.586447 0.100189 0.062 Uiso 1 1 calc R . . . .
C18 C 0.5918(4) 0.53328(15) 0.16331(9) 0.0441(5) Uani 1 1 d . . . . .
H18 H 0.465420 0.499418 0.142786 0.053 Uiso 1 1 calc R . . . .
C19 C 0.8112(5) 0.47107(15) 0.17839(9) 0.0489(5) Uani 1 1 d . . . . .
C20 C 0.5589(5) 0.53129(15) 0.25753(9) 0.0473(5) Uani 1 1 d . . . . .


_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
S1 C9 1.767(3) . ?
S1 C10 1.796(2) . ?
O1 C9 1.197(3) . ?
O2 C10 1.212(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.453(3) . ?
N1 C10 1.328(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.375(5) . ?
C1 C6 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.530(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.525(3) . ?
S2 C19 1.778(2) . ?
S2 C20 1.801(2) . ?
O3 C19 1.199(3) . ?
O4 C20 1.211(3) . ?
N2 H2A 0.8600 . ?
N2 C18 1.447(3) . ?
N2 C20 1.326(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(4) . ?
C11 C16 1.379(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 C17 1.501(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.520(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
C9 S1 C10 91.80(12) . . ?
C8 N1 H1 120.1 . . ?
C10 N1 H1 120.1 . . ?
C10 N1 C8 119.7(2) . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C6 120.9(3) . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 121.3(2) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 113.1(2) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N1 C8 C7 113.5(2) . . ?
N1 C8 H8 109.0 . . ?
N1 C8 C9 106.30(19) . . ?
C7 C8 H8 109.0 . . ?
C9 C8 C7 109.9(2) . . ?
C9 C8 H8 109.0 . . ?
O1 C9 S1 124.3(2) . . ?
O1 C9 C8 124.5(2) . . ?
C8 C9 S1 111.23(17) . . ?
O2 C10 S1 121.17(18) . . ?
O2 C10 N1 128.0(2) . . ?
N1 C10 S1 110.86(17) . . ?
C19 S2 C20 91.73(12) . . ?
C18 N2 H2A 119.8 . . ?
C20 N2 H2A 119.8 . . ?
C20 N2 C18 120.44(19) . . ?
C12 C11 H11 119.2 . . ?
C12 C11 C16 121.6(2) . . ?
C16 C11 H11 119.2 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 117.3(2) . . ?
C11 C16 C17 121.2(2) . . ?
C15 C16 C17 121.5(2) . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C16 C17 C18 113.3(2) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
N2 C18 C17 113.50(19) . . ?
N2 C18 H18 109.0 . . ?
N2 C18 C19 106.43(19) . . ?
C17 C18 H18 109.0 . . ?
C19 C18 C17 109.84(19) . . ?
C19 C18 H18 109.0 . . ?
O3 C19 S2 124.2(2) . . ?
O3 C19 C18 124.8(2) . . ?
C18 C19 S2 110.95(17) . . ?
O4 C20 S2 121.65(19) . . ?
O4 C20 N2 128.0(2) . . ?
N2 C20 S2 110.34(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
