# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_liuxc_0921_auto
_database_code_depnum_ccdc_archive 'CCDC 2375205'
loop_
_audit_author_name
_audit_author_address
'Yong Yuan'
;Northwest Normal University
China
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_audit_creation_date             2023-09-21
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5314(9)
_cell_length_b                   4.1737(2)
_cell_length_c                   14.2425(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.820(6)
_cell_angle_gamma                90
_cell_volume                     923.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    304.23(10)
_cell_measurement_theta_max      30.6690
_cell_measurement_theta_min      2.6100
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7692
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.382
_diffrn_reflns_theta_min         2.623
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.23(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  61.00   1.00    2.00    --   -6.19   5.00 124.00   80
  2  ω      2.00  32.00   1.00    2.00    --    4.16 -99.00 -30.00   30
  3  ω    -61.00   9.00   1.00    2.00    --   -6.19 -57.00 -90.00   70
  4  ω    -75.00 -50.00   1.00    2.00    --   -6.19  -5.00 -52.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405773000
_diffrn_orient_matrix_UB_12      0.0085642000
_diffrn_orient_matrix_UB_13      -0.0221099000
_diffrn_orient_matrix_UB_21      0.0207949000
_diffrn_orient_matrix_UB_22      0.0065127000
_diffrn_orient_matrix_UB_23      0.0446202000
_diffrn_orient_matrix_UB_31      0.0028575000
_diffrn_orient_matrix_UB_32      -0.1696396000
_diffrn_orient_matrix_UB_33      0.0005967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1515
_reflns_number_total             2294
_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       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.021
_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)+(0.0703P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1446
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.31747(7) 0.1778(3) 0.66454(7) 0.0655(3) Uani 1 1 d . . . . .
O2 O 0.52201(6) 0.1063(3) 0.62898(7) 0.0627(3) Uani 1 1 d . . . . .
H2 H 0.552330 0.074133 0.583274 0.094 Uiso 1 1 calc R U . . .
N1 N 0.39467(7) 0.0369(3) 0.53876(8) 0.0557(3) Uani 1 1 d . . . . .
C1 C 0.26050(9) 0.3352(3) 0.51497(10) 0.0517(4) Uani 1 1 d . . . . .
C2 C 0.26719(10) 0.3544(4) 0.41853(11) 0.0673(4) Uani 1 1 d . . . . .
H2A H 0.314950 0.267408 0.389237 0.081 Uiso 1 1 calc R U . . .
C3 C 0.20371(11) 0.5011(5) 0.36528(12) 0.0739(5) Uani 1 1 d . . . . .
H3 H 0.209313 0.510961 0.300416 0.089 Uiso 1 1 calc R U . . .
C4 C 0.13200(10) 0.6338(4) 0.40623(13) 0.0656(4) Uani 1 1 d . . . . .
C5 C 0.12580(10) 0.6149(4) 0.50230(13) 0.0718(5) Uani 1 1 d . . . . .
H5 H 0.078065 0.702806 0.531410 0.086 Uiso 1 1 calc R U . . .
C6 C 0.18896(10) 0.4683(4) 0.55663(12) 0.0653(4) Uani 1 1 d . . . . .
H6 H 0.183291 0.459037 0.621489 0.078 Uiso 1 1 calc R U . . .
C7 C 0.06274(13) 0.7922(5) 0.34688(15) 0.0899(6) Uani 1 1 d . . . . .
H7A H 0.008448 0.775078 0.377858 0.135 Uiso 1 1 calc R U . . .
H7B H 0.059016 0.687963 0.286867 0.135 Uiso 1 1 calc R U . . .
H7C H 0.076763 1.014127 0.338187 0.135 Uiso 1 1 calc R U . . .
C8 C 0.32793(9) 0.1750(3) 0.57046(9) 0.0508(3) Uani 1 1 d . . . . .
C9 C 0.38870(11) -0.0053(5) 0.70355(12) 0.0673(4) Uani 1 1 d . . . . .
H9A H 0.368530 -0.203697 0.731095 0.081 Uiso 1 1 calc R U . . .
H9B H 0.419414 0.116951 0.751278 0.081 Uiso 1 1 calc R U . . .
C10 C 0.44608(10) -0.0719(4) 0.61999(10) 0.0573(4) Uani 1 1 d . . . . .
H10 H 0.458839 -0.301245 0.615130 0.069 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0612(6) 0.0852(8) 0.0503(6) 0.0033(5) 0.0078(5) 0.0129(5)
O2 0.0522(6) 0.0782(7) 0.0577(6) -0.0164(5) -0.0027(5) 0.0015(5)
N1 0.0470(7) 0.0659(7) 0.0541(7) -0.0120(5) -0.0016(5) 0.0012(5)
C1 0.0433(7) 0.0556(8) 0.0562(8) -0.0039(6) 0.0041(6) -0.0028(6)
C2 0.0523(9) 0.0916(12) 0.0582(9) -0.0007(8) 0.0059(7) 0.0091(8)
C3 0.0636(10) 0.0966(13) 0.0615(10) 0.0071(9) -0.0018(8) 0.0041(9)
C4 0.0528(9) 0.0638(9) 0.0797(11) -0.0007(8) -0.0093(8) -0.0021(7)
C5 0.0494(9) 0.0784(11) 0.0878(12) -0.0109(9) 0.0034(8) 0.0106(8)
C6 0.0561(9) 0.0770(10) 0.0628(9) -0.0070(8) 0.0064(7) 0.0064(8)
C7 0.0703(12) 0.0871(13) 0.1117(16) 0.0040(11) -0.0223(11) 0.0090(10)
C8 0.0478(7) 0.0549(8) 0.0497(7) -0.0052(6) 0.0036(6) -0.0039(6)
C9 0.0630(9) 0.0807(11) 0.0580(9) 0.0087(8) 0.0000(7) 0.0064(8)
C10 0.0548(8) 0.0573(8) 0.0596(9) -0.0055(6) -0.0042(6) 0.0043(6)

_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 C8 1.3520(16) . ?
O1 C9 1.4489(18) . ?
O2 C10 1.3986(18) . ?
N1 C8 1.2743(17) . ?
N1 C10 1.4684(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.383(2) . ?
C1 C8 1.465(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.375(2) . ?
C4 C7 1.511(2) . ?
C5 C6 1.383(2) . ?
C9 C10 1.523(2) . ?

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
C8 O1 C9 105.87(11) . . ?
C8 N1 C10 107.25(12) . . ?
C2 C1 C6 118.40(14) . . ?
C2 C1 C8 119.98(13) . . ?
C6 C1 C8 121.62(13) . . ?
C3 C2 C1 120.62(15) . . ?
C2 C3 C4 121.37(16) . . ?
C3 C4 C7 120.75(17) . . ?
C5 C4 C3 117.76(15) . . ?
C5 C4 C7 121.49(16) . . ?
C4 C5 C6 121.51(15) . . ?
C1 C6 C5 120.34(15) . . ?
O1 C8 C1 115.82(12) . . ?
N1 C8 O1 117.72(13) . . ?
N1 C8 C1 126.46(13) . . ?
O1 C9 C10 104.41(12) . . ?
O2 C10 N1 110.84(13) . . ?
O2 C10 C9 109.48(12) . . ?
N1 C10 C9 103.98(12) . . ?

_shelx_res_file                  
;
TITL liuxc_0921_auto_a.res in P2(1)/c
    liuxc_0921_auto.res
    created by SHELXL-2018/3 at 10:13:14 on 21-Sep-2023
REM Old TITL liuxc_0921_auto in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.175, Rweak 0.260, Alpha 0.018
REM <I/s> 0.273 for 237 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N O2
CELL 0.71073 15.531359 4.173675 14.242453 90 90.8201 90
ZERR 4 0.000943 0.000236 0.000932 0 0.0055 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 40 44 4 8

L.S. 4 0 0
PLAN  2
SIZE 0.11 0.13 0.27
TEMP 31
BOND
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\liuxc_0921_auto.hkl">
REM </olex2.extras>

WGHT    0.070300    0.131500
FVAR       5.71035
O1    4    0.317471    0.177842    0.664537    11.00000    0.06118    0.08523 =
         0.05034    0.00327    0.00780    0.01292
O2    4    0.522007    0.106300    0.628982    11.00000    0.05218    0.07823 =
         0.05766   -0.01638   -0.00271    0.00154
AFIX 147
H2    2    0.552330    0.074133    0.583274    11.00000   -1.50000
AFIX   0
N1    3    0.394674    0.036936    0.538757    11.00000    0.04699    0.06588 =
         0.05407   -0.01197   -0.00160    0.00120
C1    1    0.260500    0.335241    0.514972    11.00000    0.04333    0.05561 =
         0.05618   -0.00388    0.00413   -0.00280
C2    1    0.267186    0.354353    0.418527    11.00000    0.05227    0.09160 =
         0.05822   -0.00072    0.00589    0.00910
AFIX  43
H2A   2    0.314950    0.267408    0.389237    11.00000   -1.20000
AFIX   0
C3    1    0.203706    0.501133    0.365276    11.00000    0.06357    0.09658 =
         0.06154    0.00713   -0.00177    0.00414
AFIX  43
H3    2    0.209313    0.510961    0.300416    11.00000   -1.20000
AFIX   0
C4    1    0.132000    0.633807    0.406233    11.00000    0.05283    0.06382 =
         0.07971   -0.00072   -0.00933   -0.00213
C5    1    0.125804    0.614945    0.502300    11.00000    0.04941    0.07843 =
         0.08777   -0.01094    0.00341    0.01056
AFIX  43
H5    2    0.078065    0.702806    0.531410    11.00000   -1.20000
AFIX   0
C6    1    0.188960    0.468262    0.556629    11.00000    0.05612    0.07701 =
         0.06283   -0.00696    0.00638    0.00640
AFIX  43
H6    2    0.183291    0.459037    0.621489    11.00000   -1.20000
AFIX   0
C7    1    0.062745    0.792178    0.346876    11.00000    0.07035    0.08710 =
         0.11171    0.00402   -0.02232    0.00897
AFIX 137
H7A   2    0.008448    0.775078    0.377858    11.00000   -1.50000
H7B   2    0.059016    0.687963    0.286867    11.00000   -1.50000
H7C   2    0.076763    1.014127    0.338187    11.00000   -1.50000
AFIX   0
C8    1    0.327929    0.174976    0.570465    11.00000    0.04785    0.05488 =
         0.04969   -0.00520    0.00364   -0.00390
C9    1    0.388696   -0.005337    0.703551    11.00000    0.06299    0.08074 =
         0.05805    0.00871    0.00002    0.00637
AFIX  23
H9A   2    0.368530   -0.203697    0.731095    11.00000   -1.20000
H9B   2    0.419414    0.116951    0.751278    11.00000   -1.20000
AFIX   0
C10   1    0.446078   -0.071941    0.619992    11.00000    0.05484    0.05729 =
         0.05959   -0.00547   -0.00418    0.00433
AFIX  13
H10   2    0.458839   -0.301245    0.615130    11.00000   -1.20000
AFIX   0
HKLF 4




REM  liuxc_0921_auto_a.res in P2(1)/c
REM wR2 = 0.1446, GooF = S = 1.021, Restrained GooF = 1.021 for all data
REM R1 = 0.0455 for 1515 Fo > 4sig(Fo) and 0.0707 for all 2294 data
REM 120 parameters refined using 0 restraints

END

WGHT      0.0703      0.1315

REM Highest difference peak  0.168,  deepest hole -0.153,  1-sigma level  0.037
Q1    1   0.0347  0.9910  0.3874  11.00000  0.05    0.17
Q2    1   0.0149  0.6414  0.3259  11.00000  0.05    0.16
;
_shelx_res_checksum              23784
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.787
