# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_NH-J3
_database_code_depnum_ccdc_archive 'CCDC 1897592'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 Cl4 Mn N6, 2(C5 H8 N3)'
_chemical_formula_sum            'C20 H30 Cl4 Mn N12'
_chemical_formula_weight         635.30

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'

_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                   7.6700(8)
_cell_length_b                   9.0452(10)
_cell_length_c                   11.0423(10)
_cell_angle_alpha                108.104(9)
_cell_angle_beta                 96.967(9)
_cell_angle_gamma                110.004(10)
_cell_volume                     661.63(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    121.0(4)
_cell_measurement_reflns_used    2442
_cell_measurement_theta_min      3.7950
_cell_measurement_theta_max      27.5800

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             327
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.939
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.895
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      121.0(4)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4168
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0229
_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       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2312
_reflns_number_gt                2052
_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 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.3191P] 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         2312
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT094_NH-J3               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       6.92 Report
RESPONSE: The residual density refers to one molecule of water present with
an occupation of 10 %. Due to the low occupation, attempts to construct 
a water molecule with two hydrogen atoms have not been succesful. Therefore,
it has been deleted, which resulted in the high amount of residual electron
density. The low occupation of the water molecule is due to crystals of low 
quality, where decomposition already occurred.  
;
# end Validation Reply Form


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 0.3198(4) 0.6975(3) 0.0944(2) 0.0152(5) Uani 1 1 d . . . . .
H1 H 0.2574 0.6567 0.0058 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2602(4) 0.5942(3) 0.1639(2) 0.0168(6) Uani 1 1 d . . . . .
H2 H 0.1604 0.4870 0.1243 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3572(4) 0.6589(3) 0.2961(2) 0.0144(5) Uani 1 1 d . . . . .
C4 C 0.3041(4) 0.5590(4) 0.3815(3) 0.0199(6) Uani 1 1 d . . . . .
H4A H 0.4034 0.5222 0.4021 0.030 Uiso 1 1 calc R U . . .
H4B H 0.1856 0.4617 0.3356 0.030 Uiso 1 1 calc R U . . .
H4C H 0.2892 0.6291 0.4615 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5530(4) 0.9040(3) 0.2764(2) 0.0134(5) Uani 1 1 d . . . . .
C6 C 1.1213(4) 1.2141(4) 0.8720(3) 0.0206(6) Uani 1 1 d . . . . .
H7 H 1.1853 1.2355 0.9567 0.025 Uiso 1 1 calc R U . . .
C7 C 1.1951(4) 1.3204(4) 0.8106(2) 0.0198(6) Uani 1 1 d . . . . .
H8 H 1.3099 1.4156 0.8517 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0915(4) 1.2817(3) 0.6817(3) 0.0167(6) Uani 1 1 d . . . . .
C9 C 1.1592(4) 1.3959(4) 0.6094(3) 0.0237(6) Uani 1 1 d . . . . .
H10A H 1.0576 1.3669 0.5351 0.036 Uiso 1 1 calc R U . . .
H10B H 1.2673 1.3826 0.5794 0.036 Uiso 1 1 calc R U . . .
H10C H 1.1964 1.5117 0.6671 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8623(4) 1.0393(3) 0.6841(2) 0.0164(6) Uani 1 1 d . . . . .
Cl1 Cl 0.56927(9) 0.76596(8) -0.15325(6) 0.01758(19) Uani 1 1 d . . . . .
Cl2 Cl 0.13734(9) 0.83655(8) -0.10759(6) 0.01680(19) Uani 1 1 d . . . . .
Mn1 Mn 0.5000 1.0000 0.0000 0.01298(18) Uani 1 2 d S . P . .
N1 N 0.4627(3) 0.8532(3) 0.14738(19) 0.0133(5) Uani 1 1 d . . . . .
N2 N 0.5024(3) 0.8118(3) 0.3520(2) 0.0153(5) Uani 1 1 d . . . . .
N3 N 0.7007(3) 1.0553(3) 0.3343(3) 0.0187(5) Uani 1 1 d . . . . .
N4 N 0.9549(3) 1.0774(3) 0.8101(2) 0.0190(5) Uani 1 1 d . . . . .
N5 N 0.9312(3) 1.1434(3) 0.6202(2) 0.0148(5) Uani 1 1 d . . . . .
N6 N 0.7042(4) 0.9003(3) 0.6244(3) 0.0211(5) Uani 1 1 d . . . . .
H1N H 0.763(5) 1.084(4) 0.415(3) 0.028(9) Uiso 1 1 d . . . . .
H2N H 0.740(4) 1.102(4) 0.288(3) 0.022(8) Uiso 1 1 d . . . . .
H3N H 0.646(5) 0.877(4) 0.546(3) 0.032(9) Uiso 1 1 d . . . . .
H4N H 0.657(4) 0.854(4) 0.666(3) 0.016(8) Uiso 1 1 d . . . . .
H5N H 0.901(5) 1.007(4) 0.839(3) 0.026(9) 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 N1 1.343(3) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9300 . ?
C3 N2 1.336(3) . ?
C3 C4 1.497(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N3 1.336(3) . ?
C5 N2 1.353(3) . ?
C5 N1 1.363(3) . ?
C6 N4 1.345(4) . ?
C6 C7 1.353(4) . ?
C6 H7 0.9300 . ?
C7 C8 1.416(4) . ?
C7 H8 0.9300 . ?
C8 N5 1.325(3) . ?
C8 C9 1.490(4) . ?
C9 H10A 0.9600 . ?
C9 H10B 0.9600 . ?
C9 H10C 0.9600 . ?
C10 N6 1.317(4) . ?
C10 N5 1.351(3) . ?
C10 N4 1.361(3) . ?
Cl1 Mn1 2.5276(7) . ?
Cl2 Mn1 2.5744(7) . ?
Mn1 N1 2.385(2) . ?
Mn1 N1 2.385(2) 2_675 ?
Mn1 Cl1 2.5276(7) 2_675 ?
Mn1 Cl2 2.5744(7) 2_675 ?
N3 H1N 0.87(3) . ?
N3 H2N 0.78(3) . ?
N4 H5N 0.81(3) . ?
N6 H3N 0.84(3) . ?
N6 H4N 0.76(3) . ?

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
N1 C1 C2 123.9(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 116.5(2) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
N2 C3 C2 121.5(2) . . ?
N2 C3 C4 117.2(2) . . ?
C2 C3 C4 121.3(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 N2 116.8(2) . . ?
N3 C5 N1 118.7(2) . . ?
N2 C5 N1 124.4(2) . . ?
N4 C6 C7 119.7(2) . . ?
N4 C6 H7 120.1 . . ?
C7 C6 H7 120.1 . . ?
C6 C7 C8 117.7(3) . . ?
C6 C7 H8 121.1 . . ?
C8 C7 H8 121.1 . . ?
N5 C8 C7 121.9(2) . . ?
N5 C8 C9 117.1(2) . . ?
C7 C8 C9 121.0(3) . . ?
C8 C9 H10A 109.5 . . ?
C8 C9 H10B 109.5 . . ?
H10A C9 H10B 109.5 . . ?
C8 C9 H10C 109.5 . . ?
H10A C9 H10C 109.5 . . ?
H10B C9 H10C 109.5 . . ?
N6 C10 N5 119.8(2) . . ?
N6 C10 N4 119.7(3) . . ?
N5 C10 N4 120.5(2) . . ?
N1 Mn1 N1 180.00(11) . 2_675 ?
N1 Mn1 Cl1 91.39(5) . 2_675 ?
N1 Mn1 Cl1 88.61(5) 2_675 2_675 ?
N1 Mn1 Cl1 88.60(5) . . ?
N1 Mn1 Cl1 91.40(5) 2_675 . ?
Cl1 Mn1 Cl1 180.0 2_675 . ?
N1 Mn1 Cl2 91.71(5) . 2_675 ?
N1 Mn1 Cl2 88.29(5) 2_675 2_675 ?
Cl1 Mn1 Cl2 91.20(2) 2_675 2_675 ?
Cl1 Mn1 Cl2 88.80(2) . 2_675 ?
N1 Mn1 Cl2 88.29(5) . . ?
N1 Mn1 Cl2 91.71(5) 2_675 . ?
Cl1 Mn1 Cl2 88.80(2) 2_675 . ?
Cl1 Mn1 Cl2 91.20(2) . . ?
Cl2 Mn1 Cl2 180.0 2_675 . ?
C1 N1 C5 115.5(2) . . ?
C1 N1 Mn1 113.26(15) . . ?
C5 N1 Mn1 131.15(17) . . ?
C3 N2 C5 118.2(2) . . ?
C5 N3 H1N 118(2) . . ?
C5 N3 H2N 117(2) . . ?
H1N N3 H2N 123(3) . . ?
C6 N4 C10 121.3(2) . . ?
C6 N4 H5N 126(2) . . ?
C10 N4 H5N 112(2) . . ?
C8 N5 C10 118.8(2) . . ?
C10 N6 H3N 120(2) . . ?
C10 N6 H4N 118(2) . . ?
H3N N6 H4N 121(3) . . ?

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
N1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 N2 -1.0(4) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
N4 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 N5 -2.3(4) . . . . ?
C6 C7 C8 C9 177.7(2) . . . . ?
C2 C1 N1 C5 2.1(3) . . . . ?
C2 C1 N1 Mn1 -174.30(19) . . . . ?
N3 C5 N1 C1 177.8(2) . . . . ?
N2 C5 N1 C1 -2.9(3) . . . . ?
N3 C5 N1 Mn1 -6.6(3) . . . . ?
N2 C5 N1 Mn1 172.69(17) . . . . ?
C2 C3 N2 C5 0.3(4) . . . . ?
C4 C3 N2 C5 179.8(2) . . . . ?
N3 C5 N2 C3 -178.9(2) . . . . ?
N1 C5 N2 C3 1.8(4) . . . . ?
C7 C6 N4 C10 2.8(4) . . . . ?
N6 C10 N4 C6 176.9(2) . . . . ?
N5 C10 N4 C6 -3.3(4) . . . . ?
C7 C8 N5 C10 1.9(4) . . . . ?
C9 C8 N5 C10 -178.1(2) . . . . ?
N6 C10 N5 C8 -179.3(2) . . . . ?
N4 C10 N5 C8 0.9(4) . . . . ?

_refine_diff_density_max         2.447
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4



