# Supplementary Information (SI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_37-lc
_database_code_depnum_ccdc_archive 'CCDC 2341820'
loop_
_audit_author_name
_audit_author_address
'Xinsong Lin'
;Florida State University
United States of America
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2026-04-22 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V119 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2024-03-19
_chemical_oxdiff_formula         CHNOCl
_chemical_oxdiff_usercomment     R.T.
_diffrn_orient_matrix_UB_11      0.0604557000
_diffrn_orient_matrix_UB_12      -0.1046291000
_diffrn_orient_matrix_UB_13      -0.0818931000
_diffrn_orient_matrix_UB_21      0.0120581000
_diffrn_orient_matrix_UB_22      0.1588611000
_diffrn_orient_matrix_UB_23      -0.0596850000
_diffrn_orient_matrix_UB_31      0.2023069000
_diffrn_orient_matrix_UB_32      0.0222239000
_diffrn_orient_matrix_UB_33      0.0417457000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.85 with sigma of 0.02
 H2A-H2B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.519
_oxdiff_exptl_absorpt_empirical_full_min 0.612
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C6 H9 Cl N2 O2'
_chemical_formula_moiety         'Cl, H2 O, C6 H7 N2 O'
_chemical_formula_weight         176.60
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.33530(10)
_cell_length_b                   8.04600(10)
_cell_length_c                   14.1590(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.8950(10)
_cell_angle_gamma                90
_cell_volume                     829.618(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(3)
_cell_measurement_reflns_used    11718
_cell_measurement_theta_min      6.0380
_cell_measurement_theta_max      79.6850
_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    3.731
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      299(3)
_diffrn_ambient_environment      air
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  28.00   0.50    0.15    --  -47.47  19.00  90.00   54
  2  ω    -19.00  26.00   0.50    0.15    --  -47.47  37.00  60.00   90
  3  ω      1.00  28.00   0.50    0.15    --  -47.47  19.00 -60.00   54
  4  ω     32.00  91.00   0.50    0.15    --   47.47-121.00 -98.00  118
  5  ω     44.00 110.00   0.50    0.62    --  113.25-121.00 -98.00  132
  6  ω     78.00 104.00   0.50    0.62    --  113.25 -94.00 -90.00   52
  7  ω     44.00 102.00   0.50    0.62    --  113.25-125.00 -60.00  116
  8  ω     45.00  91.00   0.50    0.62    --  113.25 -94.00 -60.00   92
  9  ω     43.00 105.00   0.50    0.62    --  113.25 -94.00  30.00  124
 10  ω     71.00 101.00   0.50    0.62    --  113.25 -94.00-180.00   60
 11  ω     48.00 112.00   0.50    0.15    --   47.47-152.00 101.00  128
 12  ω     48.00 131.00   0.50    0.62    --  113.25-152.00 101.00  166
 13  ω     66.00 100.00   0.50    0.62    --  113.25 -94.00 150.00   68
 14  ω     73.00 105.00   0.50    0.62    --  113.25 -94.00  90.00   64
 15  ω     42.00 136.00   0.50    0.62    --  113.25 -77.00  60.00  188
 16  ω     42.00 136.00   0.50    0.62    --  113.25 -77.00  60.00  188
 17  ω     46.00  92.00   0.50    0.62    --  113.25 -61.00 -60.00   92
 18  ω     83.00 109.00   0.50    0.62    --  113.25 -77.00 -90.00   52
 19  ω     44.00  70.00   0.50    0.62    --  113.25 -45.00 -60.00   52
 20  ω     42.00  68.00   0.50    0.62    --  113.25 -45.00   0.00   52
 21  ω     42.00  70.00   0.50    0.62    --  113.25 -45.00 -30.00   56
 22  ω     45.00  71.00   0.50    0.62    --  113.25 -77.00 -90.00   52
 23  ω     43.00  71.00   0.50    0.62    --  113.25 -45.00-150.00   56
 24  ω     42.00  94.00   0.50    0.62    --  113.25 -61.00-180.00  104
 25  ω     42.00  71.00   0.50    0.62    --  113.25 -45.00-120.00   58
 26  ω     42.00  71.00   0.50    0.62    --  113.25 -45.00 -90.00   58
 27  ω     42.00  71.00   0.50    0.62    --  113.25 -45.00  30.00   58
 28  ω     44.00  70.00   0.50    0.62    --  113.25 -45.00  60.00   52
 29  ω     42.00  71.00   0.50    0.62    --  113.25 -45.00  90.00   58
 30  ω     42.00  71.00   0.50    0.62    --  113.25 -45.00 120.00   58
 31  ω    138.00 172.00   0.50    0.62    --  113.25  77.00 -30.00   68
 32  ω    145.00 171.00   0.50    0.62    --  113.25  45.00 -90.00   52
 33  ω    101.00 144.00   0.50    0.62    --  113.25  45.00 -90.00   86
 34  ω    101.00 134.00   0.50    0.62    --  113.25  77.00 -30.00   66
 35  ω    100.00 178.00   0.50    0.62    --  113.25  15.00  90.00  156
 36  ω     82.00 119.00   0.50    0.15    --   47.47  57.00 -30.00   74
 37  ω     82.00 119.00   0.50    0.15    --   47.47  57.00 -60.00   74
 38  ω     41.00 178.00   0.50    0.62    --  113.25   0.00-120.00  274
 39  ω     90.00 125.00   0.50    0.62    --  113.25   0.00-120.00   70
 40  ω     98.00 178.00   0.50    0.62    --  113.25 121.00 -15.00  160
 41  ω     95.00 178.00   0.50    0.62    --  113.25 125.00 -60.00  166
 42  ω     95.00 178.00   0.50    0.62    --  113.25 125.00  60.00  166
 43  ω     77.00 164.00   0.50    0.62    --  113.25 152.00 144.00  174
 44  ω    -84.00 -10.00   0.50    0.15    --  -47.47 121.00 -15.00  148
 45  ω   -105.00 -27.00   0.50    0.15    --  -47.47 152.00 144.00  156
 46  ω   -105.00 -27.00   0.50    0.62    --  -91.75 152.00 144.00  156
 47  ω    -52.00 -19.00   0.50    0.62    --  -91.75  61.00  60.00   66
 48  ω   -164.00 -20.00   0.50    0.62    --  -91.75   0.00  60.00  288
 49  ω   -164.00 -20.00   0.50    0.62    --  -91.75   0.00  30.00  288
 50  ω   -164.00 -20.00   0.50    0.62    --  -91.75   0.00-150.00  288
 51  ω   -119.00 -82.00   0.50    0.15    --  -47.47 -57.00-180.00   74
 52  ω   -161.00 -76.00   0.50    0.62    --  -91.75-121.00 -98.00  170
 53  ω   -119.00 -82.00   0.50    0.15    --  -47.47 -57.00 -30.00   74
 54  ω   -119.00 -55.00   0.50    0.15    --  -47.47-152.00 101.00  128
;
_diffrn_reflns_number            16704
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_theta_min         6.297
_diffrn_reflns_theta_max         80.331
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1796
_reflns_number_gt                1679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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       
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_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)+(0.0620P)²+0.1287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     106
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0286
0 -1 0 0.0146
0 0 1 0.1170
0 0 -1 0.0840
1 0 0 0.0789
-1 0 0 0.0569
-3 0 5 0.0646
4 1 3 0.0856

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 0.9990 -0.0003 -0.1045 0.1587 0.0222
-0.0002 -0.9990 0.0003 0.1045 -0.1587 -0.0222
0.0001 0.0001 0.9989 -0.0818 -0.0596 0.0417
-0.0001 -0.0001 -0.9989 0.0818 0.0596 -0.0417
0.9994 -0.0008 0.0001 0.0605 0.0119 0.2022
-0.9994 0.0008 -0.0001 -0.0605 -0.0119 -0.2022
-2.9978 0.0026 4.9940 -0.5905 -0.3338 -0.3979
3.9980 0.9961 2.9965 -0.1079 0.0276 0.9561

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
Cl1 Cl 0.23284(5) 0.02090(5) 0.64639(2) 0.05362(16) Uani 1 1 d . . . . .
O2 O 0.12398(18) 0.39493(16) 0.64774(8) 0.0565(3) Uani 1 1 d D . . . .
H2A H 0.153(4) 0.292(2) 0.6507(18) 0.085 Uiso 1 1 d D U . . .
H2B H 0.140(3) 0.425(3) 0.7043(13) 0.085 Uiso 1 1 d D U . . .
O1 O 0.35184(17) 0.80889(18) 0.41403(9) 0.0675(4) Uani 1 1 d . . . . .
N1 N 0.20593(17) 0.61841(17) 0.49457(9) 0.0494(3) Uani 1 1 d . . . . .
H1A H 0.1119 0.6138 0.4521 0.059 Uiso 1 1 calc R U . . .
H1B H 0.2100 0.5579 0.5449 0.059 Uiso 1 1 calc R U . . .
N2 N 0.65190(15) 0.80209(14) 0.53376(8) 0.0405(3) Uani 1 1 d . . . . .
H2 H 0.6416 0.8496 0.4790 0.049 Uiso 1 1 calc R U . . .
C1 C 0.34455(19) 0.71863(18) 0.48256(9) 0.0437(3) Uani 1 1 d . . . . .
C2 C 0.50746(17) 0.71752(16) 0.55850(9) 0.0381(3) Uani 1 1 d . . . . .
C3 C 0.5208(2) 0.64177(19) 0.64597(10) 0.0466(3) Uani 1 1 d . . . . .
H3 H 0.4222 0.5826 0.6646 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6840(2) 0.6551(2) 0.70612(10) 0.0543(4) Uani 1 1 d . . . . .
H4 H 0.6948 0.6054 0.7659 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8299(2) 0.7414(2) 0.67772(11) 0.0535(4) Uani 1 1 d . . . . .
H5 H 0.9400 0.7490 0.7175 0.064 Uiso 1 1 calc R U . . .
C6 C 0.8108(2) 0.8162(2) 0.58987(11) 0.0487(3) Uani 1 1 d . . . . .
H6 H 0.9076 0.8760 0.5697 0.058 Uiso 1 1 calc R U . . .


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
O2 H2A 0.855(16) . ?
O2 H2B 0.832(16) . ?
O1 C1 1.2183(18) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.3246(19) . ?
N2 H2 0.8600 . ?
N2 C2 1.3407(17) . ?
N2 C6 1.3345(19) . ?
C1 C2 1.5086(17) . ?
C2 C3 1.3733(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(2) . ?
C6 H6 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
H2A O2 H2B 103(2) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C2 N2 H2 118.4 . . ?
C6 N2 H2 118.4 . . ?
C6 N2 C2 123.29(12) . . ?
O1 C1 N1 124.96(13) . . ?
O1 C1 C2 117.67(13) . . ?
N1 C1 C2 117.35(12) . . ?
N2 C2 C1 113.20(11) . . ?
N2 C2 C3 119.20(12) . . ?
C3 C2 C1 127.60(12) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.85(13) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.23(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.20(14) . . ?
C6 C5 H5 120.4 . . ?
N2 C6 C5 119.23(14) . . ?
N2 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?

