# Supplementary Information (SI) for Chemical Science.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2259710'
loop_
_audit_author_name
_audit_author_address
'Maciej Hodorowicz'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2024-10-28 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         ?
_chemical_formula_sum            'C6 H26 Cl2 Mn N6 O'
_chemical_formula_weight         324.17

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'
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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.9372(2)
_cell_length_b                   14.3092(2)
_cell_length_c                   8.86370(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1514.02(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    29388
_cell_measurement_theta_min      2.2090
_cell_measurement_theta_max      30.4540

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.218
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_T_min  0.71535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      250.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            62494
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         30.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2233
_reflns_number_gt                1895
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/4 (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)+(0.0344P)²+0.2180P] 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         2233
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_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
Mn1 Mn 0.500000 0.69602(2) 0.250000 0.03131(8) Uani 1 2 d S T P . .
Cl1 Cl 0.32319(2) 0.63664(2) 0.76367(3) 0.04123(9) Uani 1 1 d . . . . .
O1 O 0.500000 0.79845(10) 0.750000 0.0548(4) Uani 1 2 d S T P . .
N7 N 0.33360(7) 0.68520(6) 0.12960(9) 0.03567(19) Uani 1 1 d . . . . .
H7A H 0.294251 0.738181 0.143265 0.043 Uiso 1 1 calc R U . . .
H7B H 0.345090 0.677673 0.029989 0.043 Uiso 1 1 calc R U . . .
N4 N 0.40317(7) 0.59012(6) 0.39644(9) 0.03825(19) Uani 1 1 d . . . . .
H4A H 0.426400 0.531571 0.376534 0.046 Uiso 1 1 calc R U . . .
H4B H 0.414616 0.601921 0.494980 0.046 Uiso 1 1 calc R U . . .
N8 N 0.44607(8) 0.82244(6) 0.39345(10) 0.0406(2) Uani 1 1 d . . . . .
H8A H 0.371218 0.829451 0.388871 0.049 Uiso 1 1 calc R U . . .
H8B H 0.465399 0.813190 0.490447 0.049 Uiso 1 1 calc R U . . .
C5 C 0.28339(9) 0.60036(8) 0.35899(12) 0.0393(2) Uani 1 1 d . . . . .
H5A H 0.253777 0.657502 0.405066 0.047 Uiso 1 1 calc R U . . .
H5B H 0.241258 0.547069 0.399021 0.047 Uiso 1 1 calc R U . . .
C6 C 0.26979(9) 0.60500(7) 0.18932(12) 0.0391(2) Uani 1 1 d . . . . .
H6A H 0.297202 0.546988 0.143576 0.047 Uiso 1 1 calc R U . . .
H6B H 0.190356 0.611901 0.163734 0.047 Uiso 1 1 calc R U . . .
C9 C 0.50164(9) 0.90686(8) 0.33521(16) 0.0470(3) Uani 1 1 d . . . . .
H9A H 0.579594 0.908424 0.369783 0.056 Uiso 1 1 calc R U . . .
H9B H 0.463597 0.962637 0.373831 0.056 Uiso 1 1 calc R U . . .
H1O H 0.4475(16) 0.7602(13) 0.7569(18) 0.074(6) 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
Mn1 N7 2.2602(8) 3_655 ?
Mn1 N7 2.2602(8) . ?
Mn1 N8 2.3030(9) . ?
Mn1 N8 2.3030(9) 3_655 ?
Mn1 N4 2.3058(8) . ?
Mn1 N4 2.3059(8) 3_655 ?
O1 H1O 0.834(19) . ?
O1 H1O 0.834(19) 3_656 ?
N7 C6 1.4756(14) . ?
N7 H7A 0.9000 . ?
N7 H7B 0.9000 . ?
N4 C5 1.4751(14) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N8 C9 1.4716(16) . ?
N8 H8A 0.9000 . ?
N8 H8B 0.9000 . ?
C5 C6 1.5141(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C9 C9 1.511(3) 3_655 ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?

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
N7 Mn1 N7 172.15(4) 3_655 . ?
N7 Mn1 N8 92.22(3) 3_655 . ?
N7 Mn1 N8 93.94(3) . . ?
N7 Mn1 N8 93.94(3) 3_655 3_655 ?
N7 Mn1 N8 92.22(3) . 3_655 ?
N8 Mn1 N8 76.46(5) . 3_655 ?
N7 Mn1 N4 97.46(3) 3_655 . ?
N7 Mn1 N4 77.31(3) . . ?
N8 Mn1 N4 93.74(3) . . ?
N8 Mn1 N4 165.27(3) 3_655 . ?
N7 Mn1 N4 77.31(3) 3_655 3_655 ?
N7 Mn1 N4 97.46(3) . 3_655 ?
N8 Mn1 N4 165.27(3) . 3_655 ?
N8 Mn1 N4 93.74(3) 3_655 3_655 ?
N4 Mn1 N4 97.84(5) . 3_655 ?
H1O O1 H1O 98(3) . 3_656 ?
C6 N7 Mn1 109.73(6) . . ?
C6 N7 H7A 109.7 . . ?
Mn1 N7 H7A 109.7 . . ?
C6 N7 H7B 109.7 . . ?
Mn1 N7 H7B 109.7 . . ?
H7A N7 H7B 108.2 . . ?
C5 N4 Mn1 107.09(6) . . ?
C5 N4 H4A 110.3 . . ?
Mn1 N4 H4A 110.3 . . ?
C5 N4 H4B 110.3 . . ?
Mn1 N4 H4B 110.3 . . ?
H4A N4 H4B 108.6 . . ?
C9 N8 Mn1 108.97(7) . . ?
C9 N8 H8A 109.9 . . ?
Mn1 N8 H8A 109.9 . . ?
C9 N8 H8B 109.9 . . ?
Mn1 N8 H8B 109.9 . . ?
H8A N8 H8B 108.3 . . ?
N4 C5 C6 109.38(8) . . ?
N4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N7 C6 C5 109.57(8) . . ?
N7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N8 C9 C9 109.81(8) . 3_655 ?
N8 C9 H9A 109.7 . . ?
C9 C9 H9A 109.7 3_655 . ?
N8 C9 H9B 109.7 . . ?
C9 C9 H9B 109.7 3_655 . ?
H9A C9 H9B 108.2 . . ?

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
Mn1 N4 C5 C6 45.52(9) . . . . ?
Mn1 N7 C6 C5 40.61(9) . . . . ?
N4 C5 C6 N7 -59.32(11) . . . . ?
Mn1 N8 C9 C9 42.60(12) . . . 3_655 ?

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
_geom_hbond_publ_flag
N7 H7A Cl1 0.90 2.51 3.3785(9) 161.6 2_564 yes
N7 H7B Cl1 0.90 2.45 3.3194(9) 163.5 1_554 yes
N4 H4A Cl1 0.90 2.88 3.5812(9) 135.5 7_565 yes
N4 H4B Cl1 0.90 2.67 3.4568(9) 147.1 . yes
N8 H8A Cl1 0.90 2.62 3.4636(10) 156.9 2_564 yes
N8 H8B O1 0.90 2.35 3.2435(9) 174.2 . yes
C6 H6A Cl1 0.98 2.85 3.5771(11) 131.5 7_565 yes
O1 H1O Cl1 0.834(19) 2.310(19) 3.1354(11) 170.7(17) . yes

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047



