# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_mn
_database_code_depnum_ccdc_archive 'CCDC 2360551'
loop_
_audit_author_name
_audit_author_address
'Yue Wu'
;Liaocheng University
China
;
_audit_update_record             
;
2024-08-18 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 Cl3 Mn N2 O2'
_chemical_formula_weight         330.49

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6164(9)
_cell_length_b                   7.2631(7)
_cell_length_c                   18.8935(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.858(2)
_cell_angle_gamma                90.00
_cell_volume                     1300.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2406
_cell_measurement_theta_min      5.586
_cell_measurement_theta_max      57.132

_exptl_crystal_description       rod-shaped
_exptl_crystal_colour            'Dark pink'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5498
_exptl_absorpt_correction_T_max  0.8550
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5952
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2293
_reflns_number_gt                1887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0454P)²+2.7963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.081(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2293
_refine_ls_number_parameters     158
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.50056(6) 0.87432(8) 0.24164(3) 0.0242(2) Uani 1 1 d U . .
Cl1 Cl 0.47252(11) 0.84122(15) 0.10601(5) 0.0332(3) Uani 1 1 d U . .
Cl2 Cl 0.31627(10) 1.12064(13) 0.23972(6) 0.0298(3) Uani 1 1 d U . .
Cl3 Cl 0.67972(10) 1.12953(13) 0.24269(6) 0.0302(3) Uani 1 1 d U . .
O1 O 0.6257(3) 0.2122(5) 0.0613(2) 0.0372(8) Uani 1 1 d . . .
H1 H 0.592(5) 0.190(7) 0.018(3) 0.049(16) Uiso 1 1 d . . .
H2 H 0.613(5) 0.120(7) 0.078(3) 0.042(18) Uiso 1 1 d . . .
O2 O 0.5542(3) 0.9134(4) 0.36374(15) 0.0307(7) Uani 1 1 d U . .
H2A H 0.4999 0.8519 0.3832 0.046 Uiso 1 1 calc R . .
H3 H 0.536(6) 1.026(9) 0.370(4) 0.09(2) Uiso 1 1 d . . .
N1 N 0.1377(3) 0.3218(5) 0.08959(18) 0.0320(8) Uani 1 1 d U . .
H1A H 0.2181 0.3488 0.1150 0.038 Uiso 1 1 calc R . .
N2 N -0.0856(3) 0.2766(5) 0.05920(17) 0.0296(8) Uani 1 1 d U . .
H2B H -0.1739 0.2690 0.0616 0.035 Uiso 1 1 calc R . .
C1 C -0.0065(5) 0.3619(6) 0.1868(2) 0.0392(11) Uani 1 1 d U . .
H1B H -0.1050 0.3512 0.1894 0.059 Uiso 1 1 calc R . .
H1C H 0.0248 0.4849 0.1995 0.059 Uiso 1 1 calc R . .
H1E H 0.0464 0.2762 0.2196 0.059 Uiso 1 1 calc R . .
C2 C 0.0154(4) 0.3213(6) 0.1133(2) 0.0296(9) Uani 1 1 d U . .
C3 C 0.1161(4) 0.2722(6) 0.0176(2) 0.0298(9) Uani 1 1 d U . .
C4 C 0.2070(4) 0.2487(7) -0.0310(2) 0.0407(11) Uani 1 1 d U . .
H4A H 0.3037 0.2668 -0.0181 0.049 Uiso 1 1 calc R . .
C5 C 0.1469(5) 0.1972(7) -0.0992(3) 0.0455(12) Uani 1 1 d U . .
H5A H 0.2045 0.1824 -0.1337 0.055 Uiso 1 1 calc R . .
C6 C 0.0033(5) 0.1665(7) -0.1184(2) 0.0437(11) Uani 1 1 d U . .
H6B H -0.0325 0.1293 -0.1651 0.052 Uiso 1 1 calc R . .
C7 C -0.0879(5) 0.1894(6) -0.0706(2) 0.0386(10) Uani 1 1 d U . .
H7A H -0.1844 0.1695 -0.0834 0.046 Uiso 1 1 calc R . .
C8 C -0.0274(4) 0.2439(6) -0.0020(2) 0.0290(9) Uani 1 1 d 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
Mn1 0.0236(4) 0.0222(4) 0.0256(4) -0.0001(2) 0.0010(2) -0.0005(2)
Cl1 0.0349(6) 0.0378(6) 0.0261(5) 0.0009(4) 0.0028(4) -0.0057(5)
Cl2 0.0219(5) 0.0247(6) 0.0412(6) 0.0018(4) 0.0010(4) 0.0014(4)
Cl3 0.0225(5) 0.0255(6) 0.0430(6) -0.0015(4) 0.0064(4) -0.0014(4)
O1 0.0346(17) 0.047(2) 0.0302(19) 0.0006(17) 0.0059(14) -0.0034(15)
O2 0.0327(16) 0.0302(17) 0.0292(15) 0.0048(13) 0.0053(12) 0.0038(13)
N1 0.0186(16) 0.044(2) 0.0312(18) 0.0010(16) -0.0021(13) -0.0039(15)
N2 0.0190(16) 0.038(2) 0.0320(18) 0.0024(16) 0.0042(13) -0.0005(14)
C1 0.040(3) 0.046(3) 0.032(2) 0.001(2) 0.0068(19) -0.001(2)
C2 0.026(2) 0.027(2) 0.035(2) 0.0042(18) 0.0014(17) -0.0004(18)
C3 0.0231(19) 0.030(2) 0.035(2) 0.0035(18) 0.0027(16) 0.0002(17)
C4 0.024(2) 0.058(3) 0.042(2) 0.004(2) 0.0105(18) 0.005(2)
C5 0.045(3) 0.058(3) 0.037(2) 0.006(2) 0.015(2) 0.009(2)
C6 0.046(3) 0.054(3) 0.029(2) 0.005(2) -0.0002(19) 0.004(2)
C7 0.031(2) 0.045(3) 0.038(2) 0.003(2) -0.0015(18) 0.002(2)
C8 0.0222(19) 0.033(2) 0.031(2) 0.0054(18) 0.0025(16) 0.0015(17)

_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
Mn1 O2 2.294(3) . ?
Mn1 Cl2 2.5141(11) . ?
Mn1 Cl3 2.5285(11) . ?
Mn1 Cl2 2.5316(11) 2_645 ?
Mn1 Cl3 2.5358(11) 2_645 ?
Mn1 Cl1 2.5418(11) . ?
Cl2 Mn1 2.5316(11) 2_655 ?
Cl3 Mn1 2.5358(11) 2_655 ?
O1 H1 0.83(6) . ?
O1 H2 0.76(5) . ?
O2 H2A 0.8200 . ?
O2 H3 0.85(7) . ?
N1 C2 1.329(5) . ?
N1 C3 1.388(5) . ?
N1 H1A 0.8600 . ?
N2 C2 1.324(5) . ?
N2 C8 1.389(5) . ?
N2 H2B 0.8600 . ?
C1 C2 1.471(6) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1E 0.9600 . ?
C3 C8 1.382(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.371(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.385(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.373(6) . ?
C6 H6B 0.9300 . ?
C7 C8 1.383(6) . ?
C7 H7A 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
O2 Mn1 Cl2 87.88(8) . . ?
O2 Mn1 Cl3 82.30(8) . . ?
Cl2 Mn1 Cl3 87.49(4) . . ?
O2 Mn1 Cl2 85.35(8) . 2_645 ?
Cl2 Mn1 Cl2 172.68(3) . 2_645 ?
Cl3 Mn1 Cl2 94.33(4) . 2_645 ?
O2 Mn1 Cl3 90.55(8) . 2_645 ?
Cl2 Mn1 Cl3 90.36(4) . 2_645 ?
Cl3 Mn1 Cl3 172.60(3) . 2_645 ?
Cl2 Mn1 Cl3 86.95(3) 2_645 2_645 ?
O2 Mn1 Cl1 172.97(8) . . ?
Cl2 Mn1 Cl1 95.73(4) . . ?
Cl3 Mn1 Cl1 91.82(4) . . ?
Cl2 Mn1 Cl1 91.30(4) 2_645 . ?
Cl3 Mn1 Cl1 95.44(4) 2_645 . ?
Mn1 Cl2 Mn1 92.52(3) . 2_655 ?
Mn1 Cl3 Mn1 92.08(3) . 2_655 ?
H1 O1 H2 100(5) . . ?
Mn1 O2 H2A 109.5 . . ?
Mn1 O2 H3 104(5) . . ?
H2A O2 H3 107.7 . . ?
C2 N1 C3 109.7(3) . . ?
C2 N1 H1A 125.2 . . ?
C3 N1 H1A 125.2 . . ?
C2 N2 C8 109.7(3) . . ?
C2 N2 H2B 125.1 . . ?
C8 N2 H2B 125.1 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1B C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
N2 C2 N1 108.4(4) . . ?
N2 C2 C1 125.0(4) . . ?
N1 C2 C1 126.6(4) . . ?
C8 C3 C4 121.3(4) . . ?
C8 C3 N1 106.0(3) . . ?
C4 C3 N1 132.7(4) . . ?
C5 C4 C3 116.5(4) . . ?
C5 C4 H4A 121.8 . . ?
C3 C4 H4A 121.8 . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C7 C6 C5 121.9(4) . . ?
C7 C6 H6B 119.0 . . ?
C5 C6 H6B 119.0 . . ?
C6 C7 C8 116.0(4) . . ?
C6 C7 H7A 122.0 . . ?
C8 C7 H7A 122.0 . . ?
C7 C8 C3 122.3(4) . . ?
C7 C8 N2 131.6(4) . . ?
C3 C8 N2 106.1(3) . . ?

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
N2 H2B O1 0.86 1.97 2.822(4) 171.0 1_455
N1 H1A O2 0.86 2.21 3.017(4) 156.7 2_645
N1 H1A Cl2 0.86 2.90 3.385(4) 117.4 1_545
O2 H3 Cl1 0.85(7) 2.34(7) 3.178(3) 170(6) 2_655
O2 H2A O1 0.82 2.01 2.824(4) 175.1 2_655
O1 H2 Cl1 0.76(5) 2.54(5) 3.251(4) 157(5) 1_545
O1 H1 Cl1 0.83(6) 2.34(6) 3.164(4) 170(5) 3_665

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.116
