# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20240304-pym-wga-168_auto
_database_code_depnum_ccdc_archive 'CCDC 2368464'
loop_
_audit_author_name
_audit_author_address
'Cui feihu'
;School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University
China
;
_audit_update_record             
;
2024-07-06 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_audit_creation_date             2024-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Cl N2 O'
_chemical_formula_sum            'C12 H13 Cl N2 O'
_chemical_formula_weight         236.69
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
Cl Cl 0.3639 0.7018 '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      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                   8.3724(5)
_cell_length_b                   10.2633(5)
_cell_length_c                   13.8066(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1186.38(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    295.89(10)
_cell_measurement_theta_max      76.3510
_cell_measurement_theta_min      5.3510
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5283
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.835
_diffrn_reflns_theta_min         5.370
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.89(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -25.00   0.50    0.80    --  -91.75  45.00 150.00   52
  2  ω    -25.00  25.00   0.50    0.44    --  -47.52  19.00  60.00  100
  3  ω    -26.00   0.00   0.50    0.44    --  -47.52  19.00 -30.00   52
  4  ω    -25.00  26.00   0.50    0.44    --  -47.52  19.00 -60.00  102
  5  ω    -47.00 -19.00   0.50    0.80    --  -91.75  45.00 -90.00   56
  6  ω    -47.00 -21.00   0.50    0.80    --  -91.75  45.00 -60.00   52
  7  ω    -51.00 -26.00   0.50    0.80    --  -91.75  45.00 -30.00   50
  8  ω   -106.00 -66.00   0.50    0.44    --  -47.52 154.00 -86.00   80
  9  ω    -92.00 -67.00   0.50    0.80    --  -91.75 154.00 -86.00   50
 10  ω    -71.00 -46.00   0.50    0.44    --  -47.52 120.00 115.00   50
 11  ω   -109.00 -83.00   0.50    0.80    --  -91.75-120.00  31.00   52
 12  ω   -116.00 -70.00   0.50    0.44    --  -47.52-125.00  60.00   92
 13  ω     75.00 112.00   0.50    0.80    --  108.42-120.00  31.00   74
 14  ω     43.00  70.00   0.50    0.80    --  108.42 -61.00  90.00   54
 15  ω     40.00  67.00   0.50    0.80    --  108.42-120.00  31.00   54
 16  ω     38.00  70.00   0.50    0.80    --  108.42 -61.00   0.00   64
 17  ω     48.00  92.00   0.50    0.80    --  108.42-154.00-126.00   88
 18  ω     57.00 104.00   0.50    0.80    --  108.42 -77.00-120.00   94
 19  ω     94.00 119.00   0.50    0.80    --  108.42  30.00-150.00   50
 20  ω    124.00 175.00   0.50    0.80    --  108.42  30.00-150.00  102
 21  ω     88.00 113.00   0.50    0.44    --   47.52 154.00 -86.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0462203000
_diffrn_orient_matrix_UB_12      0.1385496000
_diffrn_orient_matrix_UB_13      0.0323954000
_diffrn_orient_matrix_UB_21      0.0077089000
_diffrn_orient_matrix_UB_22      -0.0464890000
_diffrn_orient_matrix_UB_23      0.1059654000
_diffrn_orient_matrix_UB_31      0.1779368000
_diffrn_orient_matrix_UB_32      -0.0342706000
_diffrn_orient_matrix_UB_33      -0.0131283000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.563
_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                1888
_reflns_number_total             2177
_reflns_odcompleteness_completeness 99.92
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.095
_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)+(0.0735P)²+0.0207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.49(3)
 0.51(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C006(H006)
3.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B)
3.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00E(H00E)
3.d Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00G(H00I,H00J,H00K)
;
_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
Cl01 Cl 0.44516(15) -0.05261(8) 0.49358(7) 0.1031(4) Uani 1 1 d . . . . .
N002 N 0.5520(3) 0.3897(2) 0.39233(14) 0.0601(5) Uani 1 1 d . . . . .
N003 N 0.4118(3) 0.3778(2) 0.53233(17) 0.0667(6) Uani 1 1 d . . . . .
O004 O 0.6168(4) 0.5623(2) 0.29753(19) 0.1008(8) Uani 1 1 d . . . . .
C005 C 0.5297(3) 0.1707(2) 0.58473(17) 0.0554(6) Uani 1 1 d . . . . .
C006 C 0.4440(3) 0.2422(2) 0.50453(19) 0.0581(6) Uani 1 1 d . . . . .
H006 H 0.341516 0.198770 0.493189 0.070 Uiso 1 1 calc R U . . .
C007 C 0.5356(4) 0.2480(2) 0.40701(17) 0.0573(6) Uani 1 1 d . . . . .
H00A H 0.639072 0.205948 0.411796 0.069 Uiso 1 1 calc R U . . .
H00B H 0.474831 0.207956 0.355145 0.069 Uiso 1 1 calc R U . . .
C008 C 0.4734(4) 0.4524(3) 0.4699(2) 0.0639(7) Uani 1 1 d . . . . .
C009 C 0.6044(3) 0.2358(3) 0.65989(19) 0.0633(7) Uani 1 1 d . . . . .
H009 H 0.606124 0.326384 0.659785 0.076 Uiso 1 1 calc R U . . .
C00A C 0.5312(4) 0.0354(3) 0.5881(2) 0.0657(7) Uani 1 1 d . . . . .
C00B C 0.6176(4) 0.4455(3) 0.3115(2) 0.0718(8) Uani 1 1 d . . . . .
C00C C 0.6000(5) -0.0327(3) 0.6634(2) 0.0823(9) Uani 1 1 d . . . . .
H00C H 0.597174 -0.123294 0.663874 0.099 Uiso 1 1 calc R U . . .
C00D C 0.6769(4) 0.1689(4) 0.7355(2) 0.0771(8) Uani 1 1 d . . . . .
H00D H 0.728242 0.214676 0.784562 0.093 Uiso 1 1 calc R U . . .
C00E C 0.6728(4) 0.0340(4) 0.7379(2) 0.0837(10) Uani 1 1 d . . . . .
H00E H 0.718756 -0.011129 0.789222 0.100 Uiso 1 1 calc R U . . .
C00F C 0.6913(5) 0.3522(4) 0.2413(2) 0.0864(10) Uani 1 1 d . . . . .
H00F H 0.767415 0.298274 0.274460 0.130 Uiso 1 1 calc R U . . .
H00G H 0.744326 0.399957 0.190896 0.130 Uiso 1 1 calc R U . . .
H00H H 0.609517 0.298378 0.213431 0.130 Uiso 1 1 calc R U . . .
C00G C 0.4641(5) 0.5977(3) 0.4787(2) 0.0871(9) Uani 1 1 d . . . . .
H00I H 0.569883 0.633723 0.477555 0.131 Uiso 1 1 calc R U . . .
H00J H 0.412953 0.620249 0.538678 0.131 Uiso 1 1 calc R U . . .
H00K H 0.403368 0.632330 0.425638 0.131 Uiso 1 1 calc 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
Cl01 C00A 1.743(3) . ?
N002 C007 1.475(3) . ?
N002 C008 1.412(4) . ?
N002 C00B 1.369(4) . ?
N003 C006 1.468(3) . ?
N003 C008 1.264(4) . ?
O004 C00B 1.214(4) . ?
C005 C006 1.510(4) . ?
C005 C009 1.384(4) . ?
C005 C00A 1.389(3) . ?
C006 H006 0.9800 . ?
C006 C007 1.551(4) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C008 C00G 1.498(4) . ?
C009 H009 0.9300 . ?
C009 C00D 1.389(4) . ?
C00A C00C 1.379(4) . ?
C00B C00F 1.496(5) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.378(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.385(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00G H00K 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
C008 N002 C007 107.6(2) . . ?
C00B N002 C007 124.2(2) . . ?
C00B N002 C008 127.9(2) . . ?
C008 N003 C006 108.7(2) . . ?
C009 C005 C006 122.0(2) . . ?
C009 C005 C00A 117.0(3) . . ?
C00A C005 C006 121.0(2) . . ?
N003 C006 C005 110.9(2) . . ?
N003 C006 H006 108.2 . . ?
N003 C006 C007 106.4(2) . . ?
C005 C006 H006 108.2 . . ?
C005 C006 C007 114.9(2) . . ?
C007 C006 H006 108.2 . . ?
N002 C007 C006 101.7(2) . . ?
N002 C007 H00A 111.4 . . ?
N002 C007 H00B 111.4 . . ?
C006 C007 H00A 111.4 . . ?
C006 C007 H00B 111.4 . . ?
H00A C007 H00B 109.3 . . ?
N002 C008 C00G 122.7(3) . . ?
N003 C008 N002 115.6(2) . . ?
N003 C008 C00G 121.7(3) . . ?
C005 C009 H009 119.3 . . ?
C005 C009 C00D 121.5(3) . . ?
C00D C009 H009 119.3 . . ?
C005 C00A Cl01 119.3(2) . . ?
C00C C00A Cl01 118.3(2) . . ?
C00C C00A C005 122.4(3) . . ?
N002 C00B C00F 115.2(3) . . ?
O004 C00B N002 122.7(3) . . ?
O004 C00B C00F 122.1(3) . . ?
C00A C00C H00C 120.1 . . ?
C00E C00C C00A 119.7(3) . . ?
C00E C00C H00C 120.1 . . ?
C009 C00D H00D 120.0 . . ?
C00E C00D C009 120.1(3) . . ?
C00E C00D H00D 120.0 . . ?
C00C C00E C00D 119.3(3) . . ?
C00C C00E H00E 120.3 . . ?
C00D C00E H00E 120.3 . . ?
C00B C00F H00F 109.5 . . ?
C00B C00F H00G 109.5 . . ?
C00B C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?
C008 C00G H00I 109.5 . . ?
C008 C00G H00J 109.5 . . ?
C008 C00G H00K 109.5 . . ?
H00I C00G H00J 109.5 . . ?
H00I C00G H00K 109.5 . . ?
H00J C00G H00K 109.5 . . ?

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
Cl01 C00A C00C C00E 178.3(3) . . . . ?
N003 C006 C007 N002 2.6(3) . . . . ?
C005 C006 C007 N002 -120.5(2) . . . . ?
C005 C009 C00D C00E -1.3(5) . . . . ?
C005 C00A C00C C00E -1.2(5) . . . . ?
C006 N003 C008 N002 0.8(3) . . . . ?
C006 N003 C008 C00G -178.8(3) . . . . ?
C006 C005 C009 C00D 177.2(3) . . . . ?
C006 C005 C00A Cl01 4.6(4) . . . . ?
C006 C005 C00A C00C -176.0(3) . . . . ?
C007 N002 C008 N003 1.0(4) . . . . ?
C007 N002 C008 C00G -179.5(3) . . . . ?
C007 N002 C00B O004 173.3(3) . . . . ?
C007 N002 C00B C00F -6.9(4) . . . . ?
C008 N002 C007 C006 -2.2(3) . . . . ?
C008 N002 C00B O004 0.9(5) . . . . ?
C008 N002 C00B C00F -179.3(3) . . . . ?
C008 N003 C006 C005 123.4(3) . . . . ?
C008 N003 C006 C007 -2.1(3) . . . . ?
C009 C005 C006 N003 -16.6(3) . . . . ?
C009 C005 C006 C007 104.0(3) . . . . ?
C009 C005 C00A Cl01 -177.8(2) . . . . ?
C009 C005 C00A C00C 1.6(5) . . . . ?
C009 C00D C00E C00C 1.7(5) . . . . ?
C00A C005 C006 N003 160.8(3) . . . . ?
C00A C005 C006 C007 -78.6(3) . . . . ?
C00A C005 C009 C00D -0.3(4) . . . . ?
C00A C00C C00E C00D -0.5(5) . . . . ?
C00B N002 C007 C006 -175.9(3) . . . . ?
C00B N002 C008 N003 174.4(3) . . . . ?
C00B N002 C008 C00G -6.1(5) . . . . ?

_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 2.025
_oxdiff_exptl_absorpt_empirical_full_min 0.560
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.49(3)
2 0.51(3)

