# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_20230207
_database_code_depnum_ccdc_archive 'CCDC 2242953'
loop_
_audit_author_name
_audit_author_address
C
;zhengzhou university
China
;
_audit_update_record             
;
2023-02-18 deposited with the CCDC.	2023-08-04 downloaded from the CCDC.
;
_audit_creation_date             2023-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O2'
_chemical_formula_sum            'C10 H13 N O2'
_chemical_formula_weight         179.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2Cl1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   20.5451(8)
_cell_length_b                   10.7614(4)
_cell_length_c                   9.2895(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.545(4)
_cell_angle_gamma                90
_cell_volume                     2036.08(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1766
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7830
_cell_measurement_theta_min      4.3290
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         4.342
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -52.00   1.00    1.50    --  -33.50-157.00-166.00   50
  2  ω   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 -90.00   93
  3  ω   -102.00 -15.00   1.00    1.50    --  -33.50 -57.00-150.00   87
  4  ω     57.00 110.00   1.00    1.50    --   36.47 178.00 -60.00   53
  5  ω    -32.00  55.00   1.00    1.50    --   36.47 -57.00   0.00   87
  6  ω    -33.00  65.00   1.00    1.50    --   36.47 -77.00 120.00   98
  7  ω     47.00 102.00   1.00    1.50    --   36.47-157.00-166.00   55
  8  ω     -4.00  66.00   1.00    1.50    --   36.47 -99.00 -90.00   70
  9  ω     64.00 104.00   1.00    1.50    --   36.47  57.00 150.00   40
 10  ω     73.00 105.00   1.00    1.50    --   36.47  57.00  60.00   32
 11  ω      9.00  92.00   1.00    1.50    --   36.47  77.00   0.00   83
 12  ω     38.00  64.00   1.00    5.00    --  108.00-111.00-120.00   26
 13  ω     44.00 121.00   1.00    5.00    --  108.00 -61.00 120.00   77
 14  ω    128.00 154.00   1.00    5.00    --  108.00  77.00-120.00   26
 15  ω     81.00 122.00   1.00    5.00    --  108.00 178.00  90.00   41
 16  ω    150.00 176.00   1.00    5.00    --  108.00  61.00 -90.00   26
 17  ω     67.00 167.00   1.00    5.00    --  108.00  15.00-150.00  100
 18  ω     67.00 133.00   1.00    5.00    --  108.00 -30.00 -60.00   66
 19  ω     41.00 128.00   1.00    5.00    --  108.00 -61.00 -30.00   87
 20  ω     91.00 117.00   1.00    5.00    --  108.00  61.00 -90.00   26
 21  ω     60.00 112.00   1.00    5.00    --  108.00-111.00 -30.00   52
 22  ω     39.00 108.00   1.00    5.00    --  108.00 -94.00 120.00   69
 23  ω     86.00 176.00   1.00    5.00    --  108.00  30.00 -90.00   90
 24  ω     42.00 122.00   1.00    5.00    --  108.00 -30.00-120.00   80
 25  ω     77.00 102.00   1.00    5.00    --  108.00-111.00-120.00   25
 26  ω     49.00  87.00   1.00    5.00    --  108.00 -61.00-150.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0642036500
_diffrn_orient_matrix_UB_12      -0.0689858500
_diffrn_orient_matrix_UB_13      0.0551327000
_diffrn_orient_matrix_UB_21      0.0388579500
_diffrn_orient_matrix_UB_22      0.1216833500
_diffrn_orient_matrix_UB_23      -0.0086993000
_diffrn_orient_matrix_UB_31      -0.0097884000
_diffrn_orient_matrix_UB_32      0.0308291000
_diffrn_orient_matrix_UB_33      0.1578796000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1331
_reflns_number_total             1816
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.036
_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)+(0.0775P)²+0.3828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1519
_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. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.21807(8) 0.23190(15) 0.23989(16) 0.0841(5) Uani 1 1 d . . . . .
O2 O 0.27877(8) 0.38835(12) 0.01645(14) 0.0688(4) Uani 1 1 d . . . . .
H2 H 0.2794 0.3481 -0.0583 0.103 Uiso 1 1 calc GR . . . .
N1 N 0.21393(9) 0.38885(16) 0.39877(17) 0.0632(5) Uani 1 1 d D . . . .
H1 H 0.2341(10) 0.4503(17) 0.440(2) 0.068(6) Uiso 1 1 d D . . . .
C1 C 0.24270(11) 0.32532(19) 0.30008(19) 0.0643(5) Uani 1 1 d . . . . .
C2 C 0.30760(11) 0.3787(2) 0.2704(2) 0.0711(6) Uani 1 1 d . . . . .
H2A H 0.3050 0.4686 0.2744 0.085 Uiso 1 1 calc R . . . .
H2B H 0.3414 0.3523 0.3472 0.085 Uiso 1 1 calc R . . . .
C3 C 0.32812(11) 0.3420(2) 0.1269(2) 0.0693(6) Uani 1 1 d . . . . .
H3 H 0.3297 0.2512 0.1206 0.083 Uiso 1 1 calc R . . . .
C4 C 0.39443(13) 0.3946(3) 0.1068(3) 0.0974(8) Uani 1 1 d . . . . .
H4A H 0.3927 0.4837 0.1096 0.146 Uiso 1 1 calc GR . . . .
H4B H 0.4060 0.3683 0.0148 0.146 Uiso 1 1 calc GR . . . .
H4C H 0.4268 0.3653 0.1833 0.146 Uiso 1 1 calc GR . . . .
C5 C 0.15280(10) 0.36804(18) 0.44917(19) 0.0609(5) Uani 1 1 d . . . . .
C6 C 0.13798(12) 0.4405(2) 0.5639(2) 0.0793(6) Uani 1 1 d . . . . .
H6 H 0.1682 0.4992 0.6046 0.095 Uiso 1 1 calc R . . . .
C7 C 0.07942(14) 0.4269(3) 0.6183(3) 0.0939(8) Uani 1 1 d . . . . .
H7 H 0.0704 0.4761 0.6957 0.113 Uiso 1 1 calc R . . . .
C8 C 0.03429(13) 0.3416(3) 0.5594(3) 0.0914(8) Uani 1 1 d . . . . .
H8 H -0.0054 0.3324 0.5963 0.110 Uiso 1 1 calc R . . . .
C9 C 0.04813(13) 0.2699(3) 0.4457(3) 0.0918(8) Uani 1 1 d . . . . .
H9 H 0.0175 0.2119 0.4054 0.110 Uiso 1 1 calc R . . . .
C10 C 0.10714(12) 0.2822(2) 0.3895(2) 0.0791(6) Uani 1 1 d . . . . .
H10 H 0.1158 0.2329 0.3120 0.095 Uiso 1 1 calc R . . . .


_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 C1 1.227(2) . ?
O2 H2 0.8200 . ?
O2 C3 1.434(3) . ?
N1 H1 0.846(16) . ?
N1 C1 1.341(3) . ?
N1 C5 1.415(3) . ?
C1 C2 1.510(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.503(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.509(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.386(3) . ?
C5 C10 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?

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
C3 O2 H2 109.5 . . ?
C1 N1 H1 118.4(15) . . ?
C1 N1 C5 129.46(18) . . ?
C5 N1 H1 112.1(15) . . ?
O1 C1 N1 122.5(2) . . ?
O1 C1 C2 123.36(19) . . ?
N1 C1 C2 114.18(18) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 C1 114.78(18) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
O2 C3 C2 106.80(17) . . ?
O2 C3 H3 109.3 . . ?
O2 C3 C4 110.26(19) . . ?
C2 C3 H3 109.3 . . ?
C2 C3 C4 112.0(2) . . ?
C4 C3 H3 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 117.37(18) . . ?
C10 C5 N1 124.00(19) . . ?
C10 C5 C6 118.6(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 C9 119.6(2) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?

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
O2 H2 O1 0.82 1.90 2.7184(19) 175.0 7
N1 H1 O2 0.846(16) 2.047(16) 2.887(2) 173(2) 6_566

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
O1 C1 C2 C3 22.0(3) . . . . ?
N1 C1 C2 C3 -158.10(18) . . . . ?
N1 C5 C6 C7 179.4(2) . . . . ?
N1 C5 C10 C9 -179.2(2) . . . . ?
C1 N1 C5 C6 173.2(2) . . . . ?
C1 N1 C5 C10 -8.0(3) . . . . ?
C1 C2 C3 O2 61.3(2) . . . . ?
C1 C2 C3 C4 -177.88(19) . . . . ?
C5 N1 C1 O1 -2.2(3) . . . . ?
C5 N1 C1 C2 177.90(18) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C5 C10 C9 -0.4(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?

_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.894
