# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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. 
# 
#######################################################################

data_20200601zh_ykd_chenhui_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2009781'
loop_
_audit_author_name
_audit_author_address
'Yaxiang Gong' 'China Pharmaceutical University'
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.0612(5)
_cell_length_b                   5.4197(2)
_cell_length_c                   13.8643(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.611(2)
_cell_angle_gamma                90
_cell_volume                     957.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9068
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      53.95

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.506
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17880
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.841
_diffrn_reflns_theta_max         54.011
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3504
_reflns_number_gt                3131
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0442P)²+0.0888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.85578(19) 0.8362(4) 0.34864(18) 0.0403(6) Uani 1 1 d . . . . .
H1 H 0.850250 0.981663 0.309626 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7866(2) 0.7986(5) 0.41012(19) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.733364 0.916648 0.412174 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7951(2) 0.5892(5) 0.46856(18) 0.0445(6) Uani 1 1 d . . . . .
H3 H 0.748321 0.564194 0.511387 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8718(2) 0.4173(5) 0.46423(19) 0.0451(6) Uani 1 1 d . . . . .
H4 H 0.877665 0.272990 0.503950 0.054 Uiso 1 1 calc R U . . .
C5 C 0.94024(19) 0.4547(5) 0.40203(18) 0.0407(6) Uani 1 1 d . . . . .
H5 H 0.992832 0.335166 0.399599 0.049 Uiso 1 1 calc R U . . .
C6 C 0.93316(18) 0.6638(4) 0.34330(17) 0.0369(5) Uani 1 1 d . . . . .
C7 C 1.00799(18) 0.7074(4) 0.27633(18) 0.0408(6) Uani 1 1 d . . . . .
H7A H 1.073335 0.614083 0.302356 0.049 Uiso 1 1 calc R U . . .
H7B H 1.026327 0.884888 0.278522 0.049 Uiso 1 1 calc R U . . .
C8 C 0.96567(17) 0.6327(4) 0.16798(18) 0.0336(5) Uani 1 1 d . . . . .
H8 H 1.019445 0.676147 0.129346 0.040 Uiso 1 1 calc R U . . .
C9 C 0.94605(18) 0.3549(4) 0.15950(18) 0.0349(5) Uani 1 1 d . . . . .
C10 C 0.3969(2) 0.2493(5) 0.28018(18) 0.0467(6) Uani 1 1 d . . . . .
H10 H 0.387770 0.106788 0.239310 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3158(2) 0.3292(6) 0.3220(2) 0.0571(8) Uani 1 1 d . . . . .
H11 H 0.251003 0.242611 0.308996 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3286(2) 0.5325(7) 0.3819(2) 0.0582(8) Uani 1 1 d . . . . .
H12 H 0.272679 0.586347 0.410556 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4217(2) 0.6588(6) 0.4007(2) 0.0553(7) Uani 1 1 d . . . . .
H13 H 0.430716 0.798792 0.442910 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5029(2) 0.5816(5) 0.35788(19) 0.0438(6) Uani 1 1 d . . . . .
H14 H 0.566999 0.671022 0.370161 0.053 Uiso 1 1 calc R U . . .
C15 C 0.49139(19) 0.3758(4) 0.29754(17) 0.0350(5) Uani 1 1 d . . . . .
C16 C 0.57871(18) 0.2901(4) 0.24921(16) 0.0363(5) Uani 1 1 d . . . . .
H16A H 0.586841 0.109097 0.256974 0.044 Uiso 1 1 calc R U . . .
H16B H 0.645462 0.367751 0.283225 0.044 Uiso 1 1 calc R U . . .
C17 C 0.55711(16) 0.3551(4) 0.13905(16) 0.0282(5) Uani 1 1 d . . . . .
H17 H 0.485485 0.295235 0.106469 0.034 Uiso 1 1 calc R U . . .
C18 C 0.56277(16) 0.6346(4) 0.12347(15) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.86681(13) 0.7649(3) 0.12414(14) 0.0318(4) Uani 1 1 d . . . . .
H1A H 0.849656 0.737030 0.057840 0.048 Uiso 1 1 calc R U . . .
H1B H 0.875883 0.929652 0.135602 0.048 Uiso 1 1 calc R U . . .
H1C H 0.814331 0.709087 0.152133 0.048 Uiso 1 1 calc R U . . .
N2 N 0.63602(13) 0.2302(3) 0.09311(13) 0.0313(4) Uani 1 1 d . . . . .
H2A H 0.618094 0.249973 0.026357 0.047 Uiso 1 1 calc R U . . .
H2B H 0.637867 0.066497 0.107972 0.047 Uiso 1 1 calc R U . . .
H2C H 0.700375 0.297726 0.116886 0.047 Uiso 1 1 calc R U . . .
O1 O 1.02439(15) 0.2207(3) 0.16521(17) 0.0621(6) Uani 1 1 d . . . . .
O2 O 0.85432(12) 0.2792(3) 0.15202(12) 0.0385(4) Uani 1 1 d . . . . .
O3 O 0.65238(11) 0.7246(3) 0.12868(13) 0.0409(4) Uani 1 1 d . . . . .
O4 O 0.47964(12) 0.7564(3) 0.10843(11) 0.0358(4) Uani 1 1 d . . . . .
O5 O 0.26837(14) 0.6826(4) 0.10208(16) 0.0707(7) Uani 1 1 d . . . . .
H5A H 0.244042 0.506757 0.107027 0.085 Uiso 1 1 d R U . . .
H5B H 0.336042 0.684057 0.126327 0.085 Uiso 1 1 d R U . . .
O6 O 0.18299(14) 0.1613(4) 0.07538(13) 0.0592(6) Uani 1 1 d . . . . .
H6A H 0.214689 -0.012247 0.084966 0.071 Uiso 1 1 d R U . . .
H6B H 0.140189 0.190253 0.111866 0.071 Uiso 1 1 d 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 1.386(4) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.506(3) . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.486(3) . ?
C8 C9 1.528(3) . ?
C8 H8 1.0000 . ?
C9 O1 1.244(3) . ?
C9 O2 1.249(3) . ?
C10 C11 1.383(4) . ?
C10 C15 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.516(3) . ?
C16 C17 1.532(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N2 1.488(3) . ?
C17 C18 1.534(3) . ?
C17 H17 1.0000 . ?
C18 O4 1.249(3) . ?
C18 O3 1.255(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
O5 H5A 1.0117 . ?
O5 H5B 0.8744 . ?
O6 H6A 1.0245 . ?
O6 H6B 0.8465 . ?

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 120.9(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 121.4(2) . . ?
C1 C6 C7 120.3(2) . . ?
C6 C7 C8 114.68(18) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 109.13(18) . . ?
N1 C8 C7 111.56(18) . . ?
C9 C8 C7 110.7(2) . . ?
N1 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O1 C9 O2 125.0(2) . . ?
O1 C9 C8 116.7(2) . . ?
O2 C9 C8 118.15(19) . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C15 C10 H10 119.8 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 118.6(2) . . ?
C14 C15 C16 121.4(2) . . ?
C10 C15 C16 119.9(2) . . ?
C15 C16 C17 112.17(18) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 109.15(17) . . ?
N2 C17 C18 109.26(17) . . ?
C16 C17 C18 111.31(18) . . ?
N2 C17 H17 109.0 . . ?
C16 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
O4 C18 O3 124.8(2) . . ?
O4 C18 C17 118.58(18) . . ?
O3 C18 C17 116.65(19) . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C17 N2 H2A 109.5 . . ?
C17 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C17 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5A O5 H5B 106.8 . . ?
H6A O6 H6B 113.2 . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031



