# Electronic Supplementary Material (ESI) for RSC Mechanochemistry.
# 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_eqV170522
_database_code_depnum_ccdc_archive 'CCDC 2268819'
loop_
_audit_author_name
_audit_author_address
'Laure Vendier'
;Laboratoire de Chimie de Coordination CNRS 
France
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2024-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl N2 O4'
_chemical_formula_sum            'C21 H15 Cl N2 O4'
_chemical_formula_weight         394.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.5285(15)
_cell_length_b                   10.8463(17)
_cell_length_c                   10.9208(16)
_cell_angle_alpha                94.939(9)
_cell_angle_beta                 113.931(8)
_cell_angle_gamma                110.838(8)
_cell_volume                     928.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      36.85

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow

_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             408

_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_T_max  0.7433


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            39871
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3787
_reflns_number_gt                3423
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0353P)²+0.7665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3609(2) 0.02555(15) 0.66677(17) 0.0198(3) Uani 1 1 d . . . . .
C1A C 0.23661(17) 0.41456(14) 0.67006(15) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.26302(18) 0.11018(14) 0.63711(15) 0.0146(3) Uani 1 1 d . . . . .
C2A C 0.28821(18) 0.39958(15) 0.80487(15) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.311460 0.323348 0.824861 0.020 Uiso 1 1 calc R U . . .
C2B C 0.2024(2) 0.52667(16) 0.64309(16) 0.0221(3) Uani 1 1 d . . . . .
H2B H 0.165706 0.537336 0.551427 0.026 Uiso 1 1 calc R U . . .
C3 C 0.31583(18) 0.22860(14) 0.60102(14) 0.0143(3) Uani 1 1 d . . . . .
C3A C 0.30604(19) 0.49471(16) 0.91028(16) 0.0200(3) Uani 1 1 d . . . . .
H3A H 0.340146 0.483567 1.001701 0.024 Uiso 1 1 calc R U . . .
C3B C 0.2207(2) 0.62329(17) 0.74746(18) 0.0255(4) Uani 1 1 d . . . . .
H3B H 0.197475 0.699683 0.728155 0.031 Uiso 1 1 calc R U . . .
C4 C 0.48788(18) 0.28985(14) 0.61690(14) 0.0152(3) Uani 1 1 d . . . . .
C4A C 0.2734(2) 0.60568(16) 0.88002(16) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.58968(18) 0.20848(15) 0.64490(14) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.74895(19) 0.26095(16) 0.65075(16) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.793074 0.348431 0.635773 0.026 Uiso 1 1 calc R U . . .
C7 C 0.8434(2) 0.18490(18) 0.67863(18) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.951875 0.220730 0.681819 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7817(2) 0.05743(18) 0.70184(17) 0.0244(3) Uani 1 1 d . . . . .
H8 H 0.847850 0.006794 0.721574 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6228(2) 0.00428(16) 0.69611(16) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.579389 -0.083127 0.711441 0.025 Uiso 1 1 calc R U . . .
C10 C 0.52745(18) 0.07983(15) 0.66773(15) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.20248(18) 0.30243(14) 0.55341(14) 0.0143(3) Uani 1 1 d . . . . .
H11 H 0.083392 0.232258 0.519429 0.017 Uiso 1 1 calc R U . . .
C12 C 0.11935(18) 0.26723(14) 0.30524(15) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.0812(2) 0.23991(16) 0.06734(16) 0.0220(3) Uani 1 1 d . . . . .
H13A H 0.052177 0.295479 0.002098 0.026 Uiso 1 1 calc R U . . .
H13B H -0.025638 0.160747 0.046118 0.026 Uiso 1 1 calc R U . . .
C14 C 0.1942(2) 0.18894(17) 0.04345(17) 0.0265(4) Uani 1 1 d . . . . .
C15 C 0.2841(3) 0.1478(2) 0.0222(2) 0.0393(5) Uani 1 1 d . . . . .
H15 H 0.349(3) 0.109(2) 0.004(2) 0.047 Uiso 1 1 d . U . . .
N1 N 0.20678(15) 0.35434(12) 0.43586(12) 0.0153(3) Uani 1 1 d . . . . .
N2 N 0.15434(17) 0.32243(13) 0.20854(13) 0.0228(3) Uani 1 1 d . . . . .
O1 O 0.01213(13) 0.14886(10) 0.27472(11) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.54967(13) 0.40855(10) 0.61017(11) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.12003(13) 0.06443(10) 0.64617(11) 0.0175(2) Uani 1 1 d . . . . .
O4 O 0.29957(18) -0.08393(13) 0.68741(18) 0.0427(4) Uani 1 1 d . . . . .
Cl1 Cl 0.30280(6) 0.72832(5) 1.01386(4) 0.03234(13) Uani 1 1 d . . . . .
H1 H 0.299320 0.424210 0.454280 0.016(4) Uiso 1 1 d . . . . .
H2 H 0.240808 0.402761 0.236869 0.027(5) Uiso 1 1 d . . . . .
H3 H 0.097110 -0.008350 0.666970 0.049(7) Uiso 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
C1 O4 1.2090(19) . ?
C1 C10 1.478(2) . ?
C1 C2 1.494(2) . ?
C1A C2B 1.392(2) . ?
C1A C2A 1.395(2) . ?
C1A C11 1.5243(19) . ?
C2 O3 1.3226(17) . ?
C2 C3 1.359(2) . ?
C2A C3A 1.389(2) . ?
C2A H2A 0.9500 . ?
C2B C3B 1.390(2) . ?
C2B H2B 0.9500 . ?
C3 C4 1.461(2) . ?
C3 C11 1.520(2) . ?
C3A C4A 1.381(2) . ?
C3A H3A 0.9500 . ?
C3B C4A 1.382(2) . ?
C3B H3B 0.9500 . ?
C4 O2 1.2336(18) . ?
C4 C5 1.493(2) . ?
C4A Cl1 1.7471(16) . ?
C5 C6 1.390(2) . ?
C5 C10 1.397(2) . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C11 N1 1.4551(17) . ?
C11 H11 1.0000 . ?
C12 O1 1.2329(17) . ?
C12 N2 1.3554(19) . ?
C12 N1 1.3658(19) . ?
C13 N2 1.453(2) . ?
C13 C14 1.469(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.185(3) . ?
C15 H15 0.93(2) . ?
N1 H1 0.8641(12) . ?
N2 O3 5.8051(18) . ?
N2 H2 0.8774(13) . ?
O3 H3 0.8191(10) . ?

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
O4 C1 C10 123.43(14) . . ?
O4 C1 C2 118.54(14) . . ?
C10 C1 C2 118.02(13) . . ?
C2B C1A C2A 118.54(13) . . ?
C2B C1A C11 121.32(13) . . ?
C2A C1A C11 119.88(12) . . ?
O3 C2 C3 120.66(13) . . ?
O3 C2 C1 117.10(12) . . ?
C3 C2 C1 122.23(13) . . ?
C3A C2A C1A 120.86(14) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C3B C2B C1A 121.37(14) . . ?
C3B C2B H2B 119.3 . . ?
C1A C2B H2B 119.3 . . ?
C2 C3 C4 119.32(13) . . ?
C2 C3 C11 120.83(13) . . ?
C4 C3 C11 119.73(12) . . ?
C4A C3A C2A 118.94(14) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
C4A C3B C2B 118.47(14) . . ?
C4A C3B H3B 120.8 . . ?
C2B C3B H3B 120.8 . . ?
O2 C4 C3 120.34(13) . . ?
O2 C4 C5 120.36(13) . . ?
C3 C4 C5 119.28(12) . . ?
C3A C4A C3B 121.82(14) . . ?
C3A C4A Cl1 118.92(12) . . ?
C3B C4A Cl1 119.25(12) . . ?
C6 C5 C10 119.20(14) . . ?
C6 C5 C4 120.27(13) . . ?
C10 C5 C4 120.52(13) . . ?
C5 C6 C7 119.73(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.95(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.70(15) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.57(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 120.85(14) . . ?
C9 C10 C1 119.60(13) . . ?
C5 C10 C1 119.51(13) . . ?
N1 C11 C3 112.29(12) . . ?
N1 C11 C1A 111.12(11) . . ?
C3 C11 C1A 113.62(11) . . ?
N1 C11 H11 106.4 . . ?
C3 C11 H11 106.4 . . ?
C1A C11 H11 106.4 . . ?
O1 C12 N2 121.76(13) . . ?
O1 C12 N1 123.41(13) . . ?
N2 C12 N1 114.79(12) . . ?
N2 C13 C14 113.73(14) . . ?
N2 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N2 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 179.05(18) . . ?
C14 C15 H15 176.0(15) . . ?
C12 N1 C11 120.22(12) . . ?
C12 N1 H1 116.63(13) . . ?
C11 N1 H1 115.77(12) . . ?
C12 N2 C13 121.29(12) . . ?
C12 N2 O3 11.26(8) . . ?
C13 N2 O3 120.59(9) . . ?
C12 N2 H2 118.38(13) . . ?
C13 N2 H2 118.60(13) . . ?
O3 N2 H2 114.94(9) . . ?
C2 O3 N2 60.54(8) . . ?
C2 O3 H3 114.04(11) . . ?
N2 O3 H3 144.89(9) . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048

