# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_A
_database_code_depnum_ccdc_archive 'CCDC 2106796'
loop_
_audit_author_name
_audit_author_address
'Xiaodong Liu' HNU
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C13H17NO2
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.1132(13)
_cell_length_b                   5.7769(7)
_cell_length_c                   20.392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1191.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4006
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      24.72

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   0.7145
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            8463
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.666
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2194
_reflns_number_gt                2020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.985

_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    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0425P)²+0.0916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2194
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.17438(17) -0.3144(2) 0.14390(8) 0.0602(4) Uani 1 1 d . . . . .
O2 O 0.07686(17) -0.3144(3) 0.02102(9) 0.0616(4) Uani 1 1 d . . . . .
H2 H 0.1152 -0.3755 0.0520 0.092 Uiso 1 1 calc R U . . .
C7 C 0.11781(19) 0.0174(3) 0.20369(10) 0.0434(5) Uani 1 1 d . . . . .
C8 C 0.0175(2) 0.2058(4) 0.19867(11) 0.0547(5) Uani 1 1 d . . . . .
H8A H 0.0598 0.3565 0.1995 0.066 Uiso 1 1 calc R U . . .
H8B H -0.0452 0.1968 0.2346 0.066 Uiso 1 1 calc R U . . .
C9 C -0.0514(2) 0.1654(4) 0.13303(12) 0.0550(6) Uani 1 1 d . . . . .
H9A H -0.0289 0.2872 0.1022 0.066 Uiso 1 1 calc R U . . .
H9B H -0.1466 0.1635 0.1388 0.066 Uiso 1 1 calc R U . . .
C10 C -0.0028(2) -0.0688(4) 0.10787(10) 0.0457(5) Uani 1 1 d . . . . .
H10 H -0.0742 -0.1822 0.1130 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2127(2) -0.0040(4) 0.25746(10) 0.0468(5) Uani 1 1 d . . . . .
C5 C 0.2127(3) 0.1673(5) 0.30590(12) 0.0608(6) Uani 1 1 d . . . . .
H5 H 0.1544 0.2912 0.3027 0.073 Uiso 1 1 calc R U . . .
C1 C 0.3030(2) -0.1846(4) 0.26404(13) 0.0602(6) Uani 1 1 d . . . . .
H1A H 0.3057 -0.3009 0.2325 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3885(3) -0.1930(6) 0.31675(14) 0.0747(8) Uani 1 1 d . . . . .
H2A H 0.4484 -0.3146 0.3202 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2984(3) 0.1544(5) 0.35850(13) 0.0738(8) Uani 1 1 d . . . . .
H4 H 0.2962 0.2689 0.3905 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3864(3) -0.0238(6) 0.36424(14) 0.0722(8) Uani 1 1 d . . . . .
H3 H 0.4440 -0.0307 0.3997 0.087 Uiso 1 1 calc R U . . .
N1 N 0.10521(15) -0.1274(3) 0.15481(8) 0.0443(4) Uani 1 1 d . . . . .
C13 C 0.1702(2) 0.0691(4) 0.02665(13) 0.0575(6) Uani 1 1 d . . . . .
H13A H 0.2415 0.0083 0.0525 0.086 Uiso 1 1 calc R U . . .
H13B H 0.1523 0.2255 0.0398 0.086 Uiso 1 1 calc R U . . .
H13C H 0.1944 0.0663 -0.0189 0.086 Uiso 1 1 calc R U . . .
C12 C -0.0627(2) -0.0054(5) -0.00954(13) 0.0679(7) Uani 1 1 d . . . . .
H12A H -0.0359 -0.0345 -0.0539 0.102 Uiso 1 1 calc R U . . .
H12B H -0.0803 0.1567 -0.0040 0.102 Uiso 1 1 calc R U . . .
H12C H -0.1413 -0.0923 0.0000 0.102 Uiso 1 1 calc R U . . .
C11 C 0.04705(19) -0.0785(4) 0.03701(10) 0.0467(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
O1 N1 1.306(2) . ?
O2 C11 1.433(3) . ?
O2 H2 0.8200 . ?
C7 N1 1.307(3) . ?
C7 C6 1.463(3) . ?
C7 C8 1.491(3) . ?
C8 C9 1.527(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.492(3) . ?
C10 C11 1.531(3) . ?
C10 H10 0.9800 . ?
C6 C1 1.393(3) . ?
C6 C5 1.398(3) . ?
C5 C4 1.381(4) . ?
C5 H5 0.9300 . ?
C1 C2 1.380(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(4) . ?
C2 H2A 0.9300 . ?
C4 C3 1.366(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C13 C11 1.524(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 C11 1.521(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C11 O2 H2 109.5 . . ?
N1 C7 C6 125.57(18) . . ?
N1 C7 C8 110.38(18) . . ?
C6 C7 C8 124.01(18) . . ?
C7 C8 C9 105.02(17) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C10 106.43(18) . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
N1 C10 C9 102.75(16) . . ?
N1 C10 C11 110.85(16) . . ?
C9 C10 C11 117.06(18) . . ?
N1 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 124.44(19) . . ?
C5 C6 C7 118.0(2) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O1 N1 C7 127.35(18) . . ?
O1 N1 C10 118.07(16) . . ?
C7 N1 C10 114.57(16) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C11 C12 105.99(18) . . ?
O2 C11 C13 109.17(17) . . ?
C12 C11 C13 110.8(2) . . ?
O2 C11 C10 108.58(18) . . ?
C12 C11 C10 109.78(17) . . ?
C13 C11 C10 112.32(18) . . ?

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
N1 C7 C8 C9 -5.8(2) . . . . ?
C6 C7 C8 C9 176.31(18) . . . . ?
C7 C8 C9 C10 9.0(2) . . . . ?
C8 C9 C10 N1 -8.7(2) . . . . ?
C8 C9 C10 C11 -130.4(2) . . . . ?
N1 C7 C6 C1 -0.4(3) . . . . ?
C8 C7 C6 C1 177.2(2) . . . . ?
N1 C7 C6 C5 -180.0(2) . . . . ?
C8 C7 C6 C5 -2.4(3) . . . . ?
C1 C6 C5 C4 -0.8(3) . . . . ?
C7 C6 C5 C4 178.8(2) . . . . ?
C5 C6 C1 C2 0.2(4) . . . . ?
C7 C6 C1 C2 -179.3(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C6 C7 N1 O1 -1.0(3) . . . . ?
C8 C7 N1 O1 -178.82(19) . . . . ?
C6 C7 N1 C10 177.93(18) . . . . ?
C8 C7 N1 C10 0.1(2) . . . . ?
C9 C10 N1 O1 -175.38(17) . . . . ?
C11 C10 N1 O1 -49.6(2) . . . . ?
C9 C10 N1 C7 5.6(2) . . . . ?
C11 C10 N1 C7 131.45(19) . . . . ?
N1 C10 C11 O2 67.6(2) . . . . ?
C9 C10 C11 O2 -175.00(17) . . . . ?
N1 C10 C11 C12 -176.91(18) . . . . ?
C9 C10 C11 C12 -59.5(2) . . . . ?
N1 C10 C11 C13 -53.2(2) . . . . ?
C9 C10 C11 C13 64.2(2) . . . . ?

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
C10 H10 O1 0.98 2.62 3.413(3) 138.2 3_445
C8 H8A O1 0.97 2.50 3.383(3) 151.5 1_565
O2 H2 N1 0.82 2.54 2.948(2) 111.9 .
O2 H2 O1 0.82 2.00 2.693(2) 141.9 .
C10 H10 O1 0.98 2.62 3.413(3) 138.2 3_445
C8 H8A O1 0.97 2.50 3.383(3) 151.5 1_565
O2 H2 N1 0.82 2.54 2.948(2) 111.9 .
O2 H2 O1 0.82 2.00 2.693(2) 141.9 .

_refine_diff_density_max         0.090
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.021



