# Electronic Supplementary Material (ESI) for ChemComm.
# 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_pre2
_database_code_depnum_ccdc_archive 'CCDC 1979545'
loop_
_audit_author_name
_audit_author_address
'Jin Kim'
;Sunchon National University
South Korea
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C16 H21 Cl Mn N3 O6, Cl O4'
_chemical_formula_sum            'C16 H21 Cl2 Mn N3 O10'
_chemical_formula_weight         541.20

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'

_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                   8.906(2)
_cell_length_b                   9.306(3)
_cell_length_c                   14.498(4)
_cell_angle_alpha                89.499(3)
_cell_angle_beta                 76.650(3)
_cell_angle_gamma                65.347(3)
_cell_volume                     1057.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9741
_cell_measurement_theta_min      1.451
_cell_measurement_theta_max      25.272

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             554
_exptl_transmission_factor_min   0.457
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.938
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9741
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.451
_diffrn_reflns_theta_max         25.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3754
_reflns_number_gt                3170
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1566P)²] 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         3754
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1900
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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 0.11157(8) 0.36126(6) 0.75250(4) 0.0155(3) Uani 1 1 d . . . . .
N1 N 0.3202(4) 0.4369(4) 0.6705(2) 0.0169(7) Uani 1 1 d . . . . .
N2 N 0.3338(5) 0.1347(4) 0.6873(2) 0.0182(8) Uani 1 1 d . . . . .
N3 N -0.0207(4) 0.6225(4) 0.7517(2) 0.0193(8) Uani 1 1 d . . . . .
O1 O 0.0134(4) 0.2756(4) 0.8812(2) 0.0281(8) Uani 1 1 d . . . . .
O2 O 0.2562(4) 0.3681(3) 0.86117(19) 0.0187(6) Uani 1 1 d . . . . .
O3 O -0.0914(4) 0.3061(4) 0.7114(2) 0.0292(7) Uani 1 1 d . . . . .
O4 O 0.0683(4) 0.3573(4) 0.5748(2) 0.0330(8) Uani 1 1 d . . . . .
O5 O -0.0700(5) 0.1935(4) 0.5609(2) 0.0446(10) Uani 1 1 d . . . . .
O6 O -0.2314(4) 0.4679(4) 0.6030(2) 0.0311(8) Uani 1 1 d . . . . .
O7 O 0.2159(5) 0.8259(5) 0.9071(3) 0.0489(10) Uani 1 1 d . . . . .
O8 O 0.4920(5) 0.6402(5) 0.9038(3) 0.0603(12) Uani 1 1 d . . . . .
O9 O 0.4029(5) 0.8969(4) 0.9669(3) 0.0436(9) Uani 1 1 d . . . . .
O10 O 0.2877(5) 0.7373(6) 1.0500(3) 0.0543(11) Uani 1 1 d . . . . .
Cl1 Cl -0.08196(13) 0.33067(11) 0.61055(7) 0.0200(3) Uani 1 1 d . . . . .
Cl2 Cl 0.34895(14) 0.77487(11) 0.95621(7) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.3507(6) -0.0102(5) 0.7141(3) 0.0214(9) Uani 1 1 d . . . . .
H1A H 0.257576 -0.017257 0.758427 0.026 Uiso 1 1 calc R U . . .
C2 C 0.4966(6) -0.1476(5) 0.6800(3) 0.0271(11) Uani 1 1 d . . . . .
H2 H 0.503596 -0.247235 0.699883 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6323(6) -0.1374(5) 0.6166(3) 0.0272(10) Uani 1 1 d . . . . .
H3 H 0.734148 -0.230544 0.591669 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6194(6) 0.0103(5) 0.5891(3) 0.0242(10) Uani 1 1 d . . . . .
H4 H 0.712102 0.019748 0.545897 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4676(6) 0.1437(4) 0.6262(3) 0.0194(9) Uani 1 1 d . . . . .
C6 C 0.4442(5) 0.3071(4) 0.5961(3) 0.0186(9) Uani 1 1 d . . . . .
H6A H 0.555769 0.312646 0.581916 0.022 Uiso 1 1 calc R U . . .
H6B H 0.404122 0.322466 0.536906 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2289(5) 0.5850(4) 0.6279(3) 0.0196(9) Uani 1 1 d . . . . .
H7A H 0.201810 0.557434 0.569955 0.024 Uiso 1 1 calc R U . . .
H7B H 0.303854 0.640040 0.609104 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0679(5) 0.6935(4) 0.6973(3) 0.0186(9) Uani 1 1 d . . . . .
C9 C 0.0078(6) 0.8584(5) 0.7032(3) 0.0243(10) Uani 1 1 d . . . . .
H9 H 0.069427 0.906375 0.662279 0.029 Uiso 1 1 calc R U . . .
C10 C -0.1422(6) 0.9511(5) 0.7690(3) 0.0263(10) Uani 1 1 d . . . . .
H10 H -0.182412 1.063359 0.775817 0.032 Uiso 1 1 calc R U . . .
C11 C -0.2328(6) 0.8791(5) 0.8248(3) 0.0282(10) Uani 1 1 d . . . . .
H11 H -0.336677 0.941095 0.870247 0.034 Uiso 1 1 calc R U . . .
C12 C -0.1708(6) 0.7155(5) 0.8138(3) 0.0223(9) Uani 1 1 d . . . . .
H12 H -0.235457 0.666515 0.851107 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3979(5) 0.4736(5) 0.7417(3) 0.0179(9) Uani 1 1 d . . . . .
H13A H 0.323961 0.582594 0.772829 0.021 Uiso 1 1 calc R U . . .
H13B H 0.510022 0.470199 0.708840 0.021 Uiso 1 1 calc R U . . .
C14 C 0.4218(6) 0.3583(5) 0.8169(3) 0.0205(9) Uani 1 1 d . . . . .
H14A H 0.499702 0.248973 0.787487 0.025 Uiso 1 1 calc R U . . .
H14B H 0.470864 0.387444 0.864402 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2621(6) 0.2483(5) 0.9264(3) 0.0265(10) Uani 1 1 d . . . . .
H15A H 0.307822 0.263603 0.979708 0.032 Uiso 1 1 calc R U . . .
H15B H 0.336149 0.140797 0.893063 0.032 Uiso 1 1 calc R U . . .
C16 C 0.0809(6) 0.2674(5) 0.9631(3) 0.0238(9) Uani 1 1 d . . . . .
H16A H 0.079129 0.175843 0.997823 0.029 Uiso 1 1 calc R U . . .
H16B H 0.012107 0.365798 1.006985 0.029 Uiso 1 1 calc R U . . .
H1 H -0.059(8) 0.273(7) 0.892(4) 0.029 Uiso 1 1 d . U . . .


_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 O1 2.164(3) . ?
Mn1 N3 2.217(3) . ?
Mn1 N2 2.224(3) . ?
Mn1 O2 2.270(3) . ?
Mn1 O3 2.272(3) . ?
Mn1 N1 2.328(3) . ?
N1 C13 1.482(5) . ?
N1 C6 1.484(5) . ?
N1 C7 1.491(5) . ?
N2 C5 1.344(6) . ?
N2 C1 1.357(5) . ?
N3 C8 1.349(5) . ?
N3 C12 1.357(6) . ?
O1 C16 1.439(5) . ?
O2 C14 1.431(5) . ?
O2 C15 1.447(5) . ?
O3 Cl1 1.467(3) . ?
O4 Cl1 1.441(3) . ?
O5 Cl1 1.423(3) . ?
O6 Cl1 1.436(3) . ?
O7 Cl2 1.432(4) . ?
O8 Cl2 1.417(4) . ?
O9 Cl2 1.427(3) . ?
O10 Cl2 1.441(4) . ?
C1 C2 1.377(6) . ?
C2 C3 1.377(7) . ?
C3 C4 1.393(6) . ?
C4 C5 1.390(6) . ?
C5 C6 1.521(5) . ?
C7 C8 1.493(6) . ?
C8 C9 1.394(5) . ?
C9 C10 1.380(7) . ?
C10 C11 1.376(7) . ?
C11 C12 1.382(6) . ?
C13 C14 1.510(5) . ?
C15 C16 1.512(7) . ?

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
O1 Mn1 N3 113.21(13) . . ?
O1 Mn1 N2 98.19(13) . . ?
N3 Mn1 N2 147.79(13) . . ?
O1 Mn1 O2 71.76(11) . . ?
N3 Mn1 O2 95.76(11) . . ?
N2 Mn1 O2 87.10(11) . . ?
O1 Mn1 O3 78.21(11) . . ?
N3 Mn1 O3 96.12(12) . . ?
N2 Mn1 O3 97.16(12) . . ?
O2 Mn1 O3 149.97(11) . . ?
O1 Mn1 N1 146.89(11) . . ?
N3 Mn1 N1 74.63(12) . . ?
N2 Mn1 N1 75.10(12) . . ?
O2 Mn1 N1 75.50(10) . . ?
O3 Mn1 N1 134.36(11) . . ?
C13 N1 C6 113.5(3) . . ?
C13 N1 C7 109.2(3) . . ?
C6 N1 C7 111.6(3) . . ?
C13 N1 Mn1 107.2(2) . . ?
C6 N1 Mn1 108.8(2) . . ?
C7 N1 Mn1 106.1(2) . . ?
C5 N2 C1 118.0(4) . . ?
C5 N2 Mn1 117.7(2) . . ?
C1 N2 Mn1 123.8(3) . . ?
C8 N3 C12 118.4(3) . . ?
C8 N3 Mn1 117.0(3) . . ?
C12 N3 Mn1 123.6(3) . . ?
C16 O1 Mn1 120.7(3) . . ?
C14 O2 C15 112.6(3) . . ?
C14 O2 Mn1 112.0(2) . . ?
C15 O2 Mn1 110.9(2) . . ?
Cl1 O3 Mn1 107.74(17) . . ?
O5 Cl1 O6 110.5(2) . . ?
O5 Cl1 O4 110.9(2) . . ?
O6 Cl1 O4 110.2(2) . . ?
O5 Cl1 O3 109.60(19) . . ?
O6 Cl1 O3 109.05(19) . . ?
O4 Cl1 O3 106.45(18) . . ?
O8 Cl2 O9 108.0(2) . . ?
O8 Cl2 O7 109.8(3) . . ?
O9 Cl2 O7 111.0(2) . . ?
O8 Cl2 O10 110.3(3) . . ?
O9 Cl2 O10 107.9(2) . . ?
O7 Cl2 O10 109.8(2) . . ?
N2 C1 C2 122.9(4) . . ?
C1 C2 C3 118.6(4) . . ?
C2 C3 C4 119.6(4) . . ?
C5 C4 C3 118.5(4) . . ?
N2 C5 C4 122.3(4) . . ?
N2 C5 C6 116.9(4) . . ?
C4 C5 C6 120.7(4) . . ?
N1 C6 C5 112.3(3) . . ?
N1 C7 C8 110.8(3) . . ?
N3 C8 C9 121.5(4) . . ?
N3 C8 C7 115.9(3) . . ?
C9 C8 C7 122.6(4) . . ?
C10 C9 C8 119.3(4) . . ?
C11 C10 C9 119.2(4) . . ?
C10 C11 C12 119.2(4) . . ?
N3 C12 C11 122.2(4) . . ?
N1 C13 C14 112.2(3) . . ?
O2 C14 C13 106.4(3) . . ?
O2 C15 C16 106.6(3) . . ?
O1 C16 C15 106.6(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
Mn1 O3 Cl1 O5 128.2(2) . . . . ?
Mn1 O3 Cl1 O6 -110.65(19) . . . . ?
Mn1 O3 Cl1 O4 8.2(2) . . . . ?
C5 N2 C1 C2 -1.4(6) . . . . ?
Mn1 N2 C1 C2 -173.1(3) . . . . ?
N2 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C1 N2 C5 C4 1.2(5) . . . . ?
Mn1 N2 C5 C4 173.3(3) . . . . ?
C1 N2 C5 C6 179.0(3) . . . . ?
Mn1 N2 C5 C6 -8.8(4) . . . . ?
C3 C4 C5 N2 -0.1(6) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C13 N1 C6 C5 86.5(4) . . . . ?
C7 N1 C6 C5 -149.5(3) . . . . ?
Mn1 N1 C6 C5 -32.8(4) . . . . ?
N2 C5 C6 N1 29.0(5) . . . . ?
C4 C5 C6 N1 -153.1(3) . . . . ?
C13 N1 C7 C8 -73.1(4) . . . . ?
C6 N1 C7 C8 160.6(3) . . . . ?
Mn1 N1 C7 C8 42.2(3) . . . . ?
C12 N3 C8 C9 -0.6(5) . . . . ?
Mn1 N3 C8 C9 -169.6(3) . . . . ?
C12 N3 C8 C7 -178.0(3) . . . . ?
Mn1 N3 C8 C7 13.0(4) . . . . ?
N1 C7 C8 N3 -38.7(5) . . . . ?
N1 C7 C8 C9 144.0(4) . . . . ?
N3 C8 C9 C10 2.8(6) . . . . ?
C7 C8 C9 C10 180.0(4) . . . . ?
C8 C9 C10 C11 -2.6(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C8 N3 C12 C11 -1.8(6) . . . . ?
Mn1 N3 C12 C11 166.5(3) . . . . ?
C10 C11 C12 N3 1.9(6) . . . . ?
C6 N1 C13 C14 -80.5(4) . . . . ?
C7 N1 C13 C14 154.3(4) . . . . ?
Mn1 N1 C13 C14 39.7(4) . . . . ?
C15 O2 C14 C13 172.2(3) . . . . ?
Mn1 O2 C14 C13 46.4(3) . . . . ?
N1 C13 C14 O2 -58.5(4) . . . . ?
C14 O2 C15 C16 -177.0(3) . . . . ?
Mn1 O2 C15 C16 -50.5(4) . . . . ?
Mn1 O1 C16 C15 -26.6(4) . . . . ?
O2 C15 C16 O1 48.7(4) . . . . ?

_refine_diff_density_max         1.395
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.180

####################################################################### 
# 
# 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_pre2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1979546'
loop_
_audit_author_name
_audit_author_address
'Jin Kim'
;Sunchon National University
South Korea
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H42 Mn2 N18 O4'
_chemical_formula_sum            'C32 H42 Mn2 N18 O4'
_chemical_formula_weight         852.71

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.8912(11)
_cell_length_b                   10.4204(11)
_cell_length_c                   16.9841(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.8018(13)
_cell_angle_gamma                90
_cell_volume                     1899.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    23415
_cell_measurement_theta_min      1.898
_cell_measurement_theta_max      25.032

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   0.698
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.728
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23415
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_full        25.032
_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             3343
_reflns_number_gt                2727
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0606P)²+3.5529P] 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         3343
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_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 0.48833(4) 0.13147(4) 0.06373(3) 0.01384(16) Uani 1 1 d . . . . .
N2 N 0.5541(2) 0.1309(3) 0.19863(15) 0.0173(6) Uani 1 1 d . . . . .
N1 N 0.3170(2) 0.0659(3) 0.12511(15) 0.0159(6) Uani 1 1 d . . . . .
N3 N 0.3450(2) 0.2864(2) 0.03392(15) 0.0169(6) Uani 1 1 d . . . . .
C8 C 0.2406(3) 0.2720(3) 0.06659(18) 0.0168(7) Uani 1 1 d . . . . .
C12 C 0.3415(3) 0.3629(3) -0.02987(19) 0.0194(7) Uani 1 1 d . . . . .
H12 H 0.415602 0.374796 -0.051509 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1299(3) 0.3319(3) 0.0334(2) 0.0217(7) Uani 1 1 d . . . . .
H9 H 0.057000 0.320410 0.056444 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5344(3) 0.0283(3) 0.32178(19) 0.0215(7) Uani 1 1 d . . . . .
H4 H 0.486724 -0.023761 0.351219 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4895(3) 0.0581(3) 0.24230(18) 0.0172(7) Uani 1 1 d . . . . .
C2 C 0.7164(3) 0.1505(3) 0.3128(2) 0.0254(8) Uani 1 1 d . . . . .
H2 H 0.795488 0.183983 0.335803 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2569(3) 0.1892(3) 0.13994(18) 0.0172(7) Uani 1 1 d . . . . .
H7A H 0.308842 0.234740 0.184831 0.021 Uiso 1 1 calc R U . . .
H7B H 0.174523 0.172149 0.155069 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6664(3) 0.1756(3) 0.2343(2) 0.0212(7) Uani 1 1 d . . . . .
H1 H 0.713134 0.226820 0.203771 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1268(3) 0.4083(3) -0.0334(2) 0.0247(8) Uani 1 1 d . . . . .
H10 H 0.051477 0.448986 -0.057162 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3681(3) 0.0021(3) 0.20100(18) 0.0203(7) Uani 1 1 d . . . . .
H6A H 0.380783 -0.089945 0.190427 0.024 Uiso 1 1 calc R U . . .
H6B H 0.306319 0.008017 0.237357 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6490(3) 0.0754(3) 0.3575(2) 0.0258(8) Uani 1 1 d . . . . .
H3 H 0.681121 0.056523 0.411816 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2342(3) 0.4252(3) -0.0654(2) 0.0227(7) Uani 1 1 d . . . . .
H11 H 0.234240 0.478422 -0.110778 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2327(3) -0.0188(3) 0.07047(19) 0.0193(7) Uani 1 1 d . . . . .
H13A H 0.272271 -0.104452 0.071128 0.023 Uiso 1 1 calc R U . . .
H13B H 0.226741 0.015589 0.015625 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1013(3) -0.0371(4) 0.0871(2) 0.0255(8) Uani 1 1 d . . . . .
H14A H 0.055734 0.045364 0.078880 0.031 Uiso 1 1 calc R U . . .
H14B H 0.057038 -0.100313 0.048953 0.031 Uiso 1 1 calc R U . . .
O1 O 0.1018(2) -0.0802(3) 0.16584(15) 0.0304(6) Uani 1 1 d . . . . .
C15 C -0.0247(3) -0.0924(4) 0.1795(2) 0.0377(10) Uani 1 1 d . . . . .
H15A H -0.067039 -0.162786 0.146307 0.045 Uiso 1 1 calc R U . . .
H15B H -0.070773 -0.011817 0.164260 0.045 Uiso 1 1 calc R U . . .
C16 C -0.0244(4) -0.1198(4) 0.2644(3) 0.0438(11) Uani 1 1 d . . . . .
H16A H 0.029883 -0.057804 0.298157 0.053 Uiso 1 1 calc R U . . .
H16B H -0.109850 -0.111868 0.276530 0.053 Uiso 1 1 calc R U . . .
O2 O 0.0217(3) -0.2500(4) 0.2812(2) 0.0666(10) Uani 1 1 d D . . . .
N4 N 0.6272(3) 0.2685(3) 0.04260(18) 0.0254(7) Uani 1 1 d . . . . .
N5 N 0.7357(3) 0.2610(3) 0.05261(17) 0.0261(7) Uani 1 1 d . . . . .
N6 N 0.8449(3) 0.2561(4) 0.0620(2) 0.0477(10) Uani 1 1 d . . . . .
N7 N 0.5711(2) -0.0614(3) 0.06263(15) 0.0195(6) Uani 1 1 d . . . . .
N8 N 0.6142(2) -0.1213(3) 0.12201(16) 0.0200(6) Uani 1 1 d . . . . .
N9 N 0.6547(3) -0.1786(3) 0.17831(18) 0.0376(8) Uani 1 1 d . . . . .
H2A H 0.072(3) -0.254(4) 0.3375(15) 0.045 Uiso 1 1 d D U . . .


_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 N4 2.154(3) . ?
Mn1 N7 2.204(3) . ?
Mn1 N3 2.243(3) . ?
Mn1 N7 2.255(3) 3_655 ?
Mn1 N2 2.281(3) . ?
Mn1 N1 2.387(2) . ?
N2 C5 1.341(4) . ?
N2 C1 1.353(4) . ?
N1 C6 1.473(4) . ?
N1 C13 1.481(4) . ?
N1 C7 1.483(4) . ?
N3 C12 1.341(4) . ?
N3 C8 1.356(4) . ?
C8 C9 1.389(4) . ?
C8 C7 1.501(4) . ?
C12 C11 1.382(5) . ?
C9 C10 1.383(5) . ?
C4 C3 1.382(5) . ?
C4 C5 1.390(5) . ?
C5 C6 1.505(4) . ?
C2 C1 1.376(5) . ?
C2 C3 1.384(5) . ?
C10 C11 1.382(5) . ?
C13 C14 1.517(4) . ?
C14 O1 1.410(4) . ?
O1 C15 1.442(4) . ?
C15 C16 1.469(6) . ?
C16 O2 1.458(6) . ?
N4 N5 1.168(4) . ?
N5 N6 1.173(4) . ?
N7 N8 1.211(4) . ?
N8 N9 1.150(4) . ?

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
N4 Mn1 N7 107.67(11) . . ?
N4 Mn1 N3 88.09(10) . . ?
N7 Mn1 N3 157.56(10) . . ?
N4 Mn1 N7 98.73(11) . 3_655 ?
N7 Mn1 N7 75.42(11) . 3_655 ?
N3 Mn1 N7 86.69(10) . 3_655 ?
N4 Mn1 N2 93.43(10) . . ?
N7 Mn1 N2 86.99(9) . . ?
N3 Mn1 N2 108.41(9) . . ?
N7 Mn1 N2 160.96(10) 3_655 . ?
N4 Mn1 N1 152.35(10) . . ?
N7 Mn1 N1 95.37(10) . . ?
N3 Mn1 N1 74.87(9) . . ?
N7 Mn1 N1 101.78(9) 3_655 . ?
N2 Mn1 N1 72.27(9) . . ?
C5 N2 C1 117.8(3) . . ?
C5 N2 Mn1 116.9(2) . . ?
C1 N2 Mn1 123.7(2) . . ?
C6 N1 C13 112.4(2) . . ?
C6 N1 C7 110.8(2) . . ?
C13 N1 C7 112.2(2) . . ?
C6 N1 Mn1 107.73(17) . . ?
C13 N1 Mn1 110.15(18) . . ?
C7 N1 Mn1 103.13(18) . . ?
C12 N3 C8 119.1(3) . . ?
C12 N3 Mn1 122.3(2) . . ?
C8 N3 Mn1 115.4(2) . . ?
N3 C8 C9 121.0(3) . . ?
N3 C8 C7 114.5(3) . . ?
C9 C8 C7 124.5(3) . . ?
N3 C12 C11 122.5(3) . . ?
C10 C9 C8 119.3(3) . . ?
C3 C4 C5 119.3(3) . . ?
N2 C5 C4 122.2(3) . . ?
N2 C5 C6 117.6(3) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C2 C3 118.7(3) . . ?
N1 C7 C8 110.5(2) . . ?
N2 C1 C2 123.2(3) . . ?
C11 C10 C9 119.5(3) . . ?
N1 C6 C5 113.8(3) . . ?
C4 C3 C2 118.9(3) . . ?
C10 C11 C12 118.6(3) . . ?
N1 C13 C14 117.5(3) . . ?
O1 C14 C13 111.4(3) . . ?
C14 O1 C15 109.4(3) . . ?
O1 C15 C16 109.4(3) . . ?
O2 C16 C15 108.4(4) . . ?
N5 N4 Mn1 130.8(3) . . ?
N4 N5 N6 178.5(4) . . ?
N8 N7 Mn1 124.3(2) . . ?
N8 N7 Mn1 129.3(2) . 3_655 ?
Mn1 N7 Mn1 104.58(11) . 3_655 ?
N9 N8 N7 179.6(4) . . ?

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
C12 N3 C8 C9 2.1(5) . . . . ?
Mn1 N3 C8 C9 -157.8(2) . . . . ?
C12 N3 C8 C7 -177.3(3) . . . . ?
Mn1 N3 C8 C7 22.8(3) . . . . ?
C8 N3 C12 C11 -2.0(5) . . . . ?
Mn1 N3 C12 C11 156.5(3) . . . . ?
N3 C8 C9 C10 -0.7(5) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
C1 N2 C5 C4 0.1(4) . . . . ?
Mn1 N2 C5 C4 166.3(2) . . . . ?
C1 N2 C5 C6 -176.4(3) . . . . ?
Mn1 N2 C5 C6 -10.3(4) . . . . ?
C3 C4 C5 N2 0.2(5) . . . . ?
C3 C4 C5 C6 176.7(3) . . . . ?
C6 N1 C7 C8 162.5(2) . . . . ?
C13 N1 C7 C8 -71.0(3) . . . . ?
Mn1 N1 C7 C8 47.5(3) . . . . ?
N3 C8 C7 N1 -50.3(4) . . . . ?
C9 C8 C7 N1 130.4(3) . . . . ?
C5 N2 C1 C2 -0.4(5) . . . . ?
Mn1 N2 C1 C2 -165.5(2) . . . . ?
C3 C2 C1 N2 0.3(5) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C13 N1 C6 C5 155.7(3) . . . . ?
C7 N1 C6 C5 -77.9(3) . . . . ?
Mn1 N1 C6 C5 34.2(3) . . . . ?
N2 C5 C6 N1 -17.9(4) . . . . ?
C4 C5 C6 N1 165.4(3) . . . . ?
C5 C4 C3 C2 -0.3(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
N3 C12 C11 C10 0.4(5) . . . . ?
C6 N1 C13 C14 78.2(4) . . . . ?
C7 N1 C13 C14 -47.4(4) . . . . ?
Mn1 N1 C13 C14 -161.7(2) . . . . ?
N1 C13 C14 O1 -54.9(4) . . . . ?
C13 C14 O1 C15 178.3(3) . . . . ?
C14 O1 C15 C16 -172.2(3) . . . . ?
O1 C15 C16 O2 -70.5(4) . . . . ?

_refine_diff_density_max         1.837
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.086

