# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_10854
_database_code_depnum_ccdc_archive 'CCDC 2053116'
loop_
_audit_author_name
_audit_author_address
'Chuancong Zhou'
;LiaoCheng University
China
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-07-07 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            'C14 H8 Mn1.50 N O7'
_chemical_formula_weight         384.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   9.1618(3)
_cell_length_b                   13.5269(5)
_cell_length_c                   21.5410(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.109(3)
_cell_angle_gamma                90
_cell_volume                     2642.91(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3824
_cell_measurement_theta_min      3.2670
_cell_measurement_theta_max      70.8650

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_F_000             1540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    12.249
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8477
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.146
_diffrn_reflns_theta_max         67.244
_diffrn_reflns_theta_full        67.244
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2373
_reflns_number_gt                2034
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    diamond
_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)+(0.0714P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Mn2 Mn 0.65102(6) -0.04541(4) 0.81287(2) 0.01524(18) Uani 1 1 d . . . . .
Mn1 Mn 0.000000 0.02467(6) 0.750000 0.0139(2) Uani 1 2 d S T P . .
N1 N 0.5599(3) 0.0269(2) 0.89536(13) 0.0188(7) Uani 1 1 d . . . . .
O1 O 1.1442(3) 0.0769(3) 1.09401(14) 0.0437(8) Uani 1 1 d . . . . .
O2 O 1.1100(3) 0.08225(19) 1.19306(11) 0.0229(6) Uani 1 1 d . . . . .
O3 O 0.7979(3) 0.39417(19) 1.20576(12) 0.0243(6) Uani 1 1 d . . . . .
O4 O 0.5607(3) 0.35353(18) 1.18808(12) 0.0234(6) Uani 1 1 d . . . . .
O5 O 0.1956(3) 0.02683(19) 0.81713(11) 0.0230(6) Uani 1 1 d . . . . .
O6 O 0.4015(3) -0.04317(17) 0.79166(11) 0.0180(5) Uani 1 1 d . . . . .
C1 C 1.0658(4) 0.0969(3) 1.13412(17) 0.0205(8) Uani 1 1 d . . . . .
C2 C 0.9188(4) 0.1451(3) 1.11660(16) 0.0170(7) Uani 1 1 d . . . . .
C3 C 0.8722(4) 0.2157(3) 1.15521(16) 0.0179(7) Uani 1 1 d . . . . .
H3 H 0.933105 0.234688 1.191492 0.021 Uiso 1 1 calc R U . . .
C4 C 0.7340(4) 0.2590(3) 1.14011(15) 0.0163(7) Uani 1 1 d . . . . .
C5 C 0.6413(4) 0.2283(3) 1.08734(16) 0.0181(7) Uani 1 1 d . . . . .
H5 H 0.547183 0.255109 1.078703 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6870(4) 0.1577(3) 1.04679(15) 0.0165(7) Uani 1 1 d . . . . .
C7 C 0.8290(4) 0.1184(3) 1.06189(16) 0.0187(7) Uani 1 1 d . . . . .
H7A H 0.863718 0.073589 1.034698 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6929(4) 0.3413(3) 1.18084(16) 0.0183(8) Uani 1 1 d . . . . .
C9 C 0.5884(4) 0.1235(3) 0.99004(16) 0.0180(7) Uani 1 1 d . . . . .
C10 C 0.4390(4) 0.1466(3) 0.97869(18) 0.0282(9) Uani 1 1 d . . . . .
H10 H 0.397186 0.186327 1.006704 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3525(4) 0.1103(3) 0.92562(17) 0.0284(9) Uani 1 1 d . . . . .
H11 H 0.252793 0.126019 0.917457 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4163(4) 0.0507(3) 0.88509(16) 0.0169(7) Uani 1 1 d . . . . .
C13 C 0.6415(4) 0.0635(3) 0.94588(16) 0.0206(8) Uani 1 1 d . . . . .
H13 H 0.741336 0.047995 0.952182 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3304(4) 0.0079(3) 0.82649(16) 0.0169(7) Uani 1 1 d . . . . .
O7 O 0.6424(3) -0.2079(2) 0.81813(15) 0.0372(7) Uani 1 1 d . . . . .
H7D H 0.588298 -0.222312 0.783958 0.045 Uiso 1 1 d R U . . .
H7B H 0.594047 -0.231822 0.845517 0.045 Uiso 1 1 d R 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
Mn2 O3 2.149(3) 7_657 ?
Mn2 O7 2.203(3) . ?
Mn2 O6 2.235(2) 2_656 ?
Mn2 O2 2.266(2) 5_757 ?
Mn2 O6 2.267(2) . ?
Mn2 N1 2.287(3) . ?
Mn1 O5 2.138(2) 2_556 ?
Mn1 O5 2.138(2) . ?
Mn1 O2 2.228(2) 6_455 ?
Mn1 O2 2.228(3) 5_657 ?
Mn1 O4 2.239(2) 7_557 ?
Mn1 O4 2.239(2) 8_455 ?
N1 C13 1.326(4) . ?
N1 C12 1.341(4) . ?
O1 C1 1.229(4) . ?
O2 C1 1.292(4) . ?
O3 C8 1.257(4) . ?
O4 C8 1.254(4) . ?
O5 C14 1.250(4) . ?
O6 C14 1.266(4) . ?
C1 C2 1.496(5) . ?
C2 C3 1.374(5) . ?
C2 C7 1.386(5) . ?
C3 C4 1.391(4) . ?
C4 C5 1.383(5) . ?
C4 C8 1.498(5) . ?
C5 C6 1.397(5) . ?
C6 C7 1.401(5) . ?
C6 C9 1.487(5) . ?
C9 C13 1.389(5) . ?
C9 C10 1.392(5) . ?
C10 C11 1.385(5) . ?
C11 C12 1.378(5) . ?
C12 C14 1.506(5) . ?

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
O3 Mn2 O7 165.89(10) 7_657 . ?
O3 Mn2 O6 79.67(9) 7_657 2_656 ?
O7 Mn2 O6 93.51(10) . 2_656 ?
O3 Mn2 O2 87.79(9) 7_657 5_757 ?
O7 Mn2 O2 79.95(9) . 5_757 ?
O6 Mn2 O2 91.08(9) 2_656 5_757 ?
O3 Mn2 O6 100.92(9) 7_657 . ?
O7 Mn2 O6 88.92(9) . . ?
O6 Mn2 O6 74.28(9) 2_656 . ?
O2 Mn2 O6 161.10(9) 5_757 . ?
O3 Mn2 N1 81.42(10) 7_657 . ?
O7 Mn2 N1 111.54(11) . . ?
O6 Mn2 N1 136.59(10) 2_656 . ?
O2 Mn2 N1 126.82(10) 5_757 . ?
O6 Mn2 N1 71.49(9) . . ?
O5 Mn1 O5 178.44(14) 2_556 . ?
O5 Mn1 O2 92.16(9) 2_556 6_455 ?
O5 Mn1 O2 88.86(9) . 6_455 ?
O5 Mn1 O2 88.85(9) 2_556 5_657 ?
O5 Mn1 O2 92.16(9) . 5_657 ?
O2 Mn1 O2 99.02(14) 6_455 5_657 ?
O5 Mn1 O4 97.92(10) 2_556 7_557 ?
O5 Mn1 O4 80.92(9) . 7_557 ?
O2 Mn1 O4 167.35(9) 6_455 7_557 ?
O2 Mn1 O4 88.85(10) 5_657 7_557 ?
O5 Mn1 O4 80.92(9) 2_556 8_455 ?
O5 Mn1 O4 97.92(10) . 8_455 ?
O2 Mn1 O4 88.85(10) 6_455 8_455 ?
O2 Mn1 O4 167.35(9) 5_657 8_455 ?
O4 Mn1 O4 85.24(13) 7_557 8_455 ?
C13 N1 C12 118.2(3) . . ?
C13 N1 Mn2 124.9(2) . . ?
C12 N1 Mn2 115.5(2) . . ?
C1 O2 Mn1 122.5(2) . 5_657 ?
C1 O2 Mn2 98.6(2) . 5_757 ?
Mn1 O2 Mn2 113.83(10) 5_657 5_757 ?
C8 O3 Mn2 129.5(2) . 7_657 ?
C8 O4 Mn1 119.8(2) . 7_557 ?
C14 O5 Mn1 145.2(2) . . ?
C14 O6 Mn2 123.3(2) . 2_656 ?
C14 O6 Mn2 118.4(2) . . ?
Mn2 O6 Mn2 105.70(9) 2_656 . ?
O1 C1 O2 121.6(3) . . ?
O1 C1 C2 120.9(3) . . ?
O2 C1 C2 117.5(3) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 119.7(3) . . ?
C7 C2 C1 120.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 C8 121.9(3) . . ?
C3 C4 C8 118.1(3) . . ?
C4 C5 C6 121.0(3) . . ?
C5 C6 C7 117.6(3) . . ?
C5 C6 C9 121.7(3) . . ?
C7 C6 C9 120.6(3) . . ?
C2 C7 C6 121.3(3) . . ?
O4 C8 O3 124.5(3) . . ?
O4 C8 C4 119.8(3) . . ?
O3 C8 C4 115.6(3) . . ?
C13 C9 C10 116.2(3) . . ?
C13 C9 C6 120.9(3) . . ?
C10 C9 C6 122.9(3) . . ?
C11 C10 C9 120.0(3) . . ?
C12 C11 C10 119.0(3) . . ?
N1 C12 C11 122.0(3) . . ?
N1 C12 C14 115.5(3) . . ?
C11 C12 C14 122.5(3) . . ?
N1 C13 C9 124.7(3) . . ?
O5 C14 O6 126.6(3) . . ?
O5 C14 C12 116.4(3) . . ?
O6 C14 C12 117.1(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 O2 C1 O1 -116.2(4) 5_657 . . . ?
Mn2 O2 C1 O1 9.3(4) 5_757 . . . ?
Mn1 O2 C1 C2 67.4(4) 5_657 . . . ?
Mn2 O2 C1 C2 -167.1(3) 5_757 . . . ?
O1 C1 C2 C3 -141.9(4) . . . . ?
O2 C1 C2 C3 34.5(5) . . . . ?
O1 C1 C2 C7 38.4(6) . . . . ?
O2 C1 C2 C7 -145.1(3) . . . . ?
C7 C2 C3 C4 1.3(5) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 2.3(5) . . . . ?
C2 C3 C4 C8 -175.2(3) . . . . ?
C3 C4 C5 C6 -3.3(5) . . . . ?
C8 C4 C5 C6 174.1(3) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C4 C5 C6 C9 179.6(3) . . . . ?
C3 C2 C7 C6 -4.0(5) . . . . ?
C1 C2 C7 C6 175.6(3) . . . . ?
C5 C6 C7 C2 2.9(5) . . . . ?
C9 C6 C7 C2 -176.0(3) . . . . ?
Mn1 O4 C8 O3 -0.8(5) 7_557 . . . ?
Mn1 O4 C8 C4 179.2(2) 7_557 . . . ?
Mn2 O3 C8 O4 -69.5(5) 7_657 . . . ?
Mn2 O3 C8 C4 110.5(3) 7_657 . . . ?
C5 C4 C8 O4 33.6(5) . . . . ?
C3 C4 C8 O4 -148.9(3) . . . . ?
C5 C4 C8 O3 -146.4(3) . . . . ?
C3 C4 C8 O3 31.1(5) . . . . ?
C5 C6 C9 C13 171.3(3) . . . . ?
C7 C6 C9 C13 -9.8(5) . . . . ?
C5 C6 C9 C10 -10.5(6) . . . . ?
C7 C6 C9 C10 168.4(4) . . . . ?
C13 C9 C10 C11 -0.1(6) . . . . ?
C6 C9 C10 C11 -178.4(4) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C13 N1 C12 C11 -0.8(5) . . . . ?
Mn2 N1 C12 C11 -167.9(3) . . . . ?
C13 N1 C12 C14 179.1(3) . . . . ?
Mn2 N1 C12 C14 12.0(4) . . . . ?
C10 C11 C12 N1 -0.2(6) . . . . ?
C10 C11 C12 C14 179.8(4) . . . . ?
C12 N1 C13 C9 1.4(6) . . . . ?
Mn2 N1 C13 C9 167.2(3) . . . . ?
C10 C9 C13 N1 -1.0(6) . . . . ?
C6 C9 C13 N1 177.4(3) . . . . ?
Mn1 O5 C14 O6 -13.6(7) . . . . ?
Mn1 O5 C14 C12 166.2(3) . . . . ?
Mn2 O6 C14 O5 34.4(5) 2_656 . . . ?
Mn2 O6 C14 O5 170.7(3) . . . . ?
Mn2 O6 C14 C12 -145.4(2) 2_656 . . . ?
Mn2 O6 C14 C12 -9.0(4) . . . . ?
N1 C12 C14 O5 177.9(3) . . . . ?
C11 C12 C14 O5 -2.1(5) . . . . ?
N1 C12 C14 O6 -2.3(5) . . . . ?
C11 C12 C14 O6 177.7(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
_geom_hbond_publ_flag
O7 H7D O4 0.85 2.71 3.420(4) 142.3 6 yes

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.094



####################################################################### 
# 
# 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_exp_11220
_database_code_depnum_ccdc_archive 'CCDC 2054576'
loop_
_audit_author_name
_audit_author_address
'Chuancong Zhou'
;Liaocheng University
China
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-07-07 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            'C14 H16 Mn1.50 N O11'
_chemical_formula_weight         456.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.4443(5)
_cell_length_b                   9.2427(6)
_cell_length_c                   12.6409(7)
_cell_angle_alpha                99.620(5)
_cell_angle_beta                 91.660(5)
_cell_angle_gamma                106.133(6)
_cell_volume                     821.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2831
_cell_measurement_theta_min      5.0700
_cell_measurement_theta_max      71.0770

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             465
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    10.153
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5035
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.558
_diffrn_reflns_theta_max         67.223
_diffrn_reflns_theta_full        67.223
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2919
_reflns_number_gt                2529
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    diamond
_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)+(0.0907P)²+0.9597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2919
_refine_ls_number_parameters     250
_refine_ls_number_restraints     660
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.018
_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 0.500000 1.000000 0.500000 0.0217(2) Uani 1 2 d S U P . .
Mn2 Mn 0.15384(9) 0.38928(6) 0.35567(4) 0.0224(2) Uani 1 1 d . U . . .
N1 N 0.2140(5) 0.4786(3) 0.1989(2) 0.0217(7) Uani 1 1 d . U . . .
O1 O 0.1129(7) -0.1064(4) -0.1539(3) 0.0701(14) Uani 1 1 d . U . . .
O2 O -0.0350(5) -0.1407(3) -0.3123(2) 0.0345(7) Uani 1 1 d . U . . .
O3 O 0.1696(5) 0.3508(3) -0.4789(2) 0.0307(7) Uani 1 1 d . U . . .
O4 O 0.1015(4) 0.5468(3) -0.3788(2) 0.0279(6) Uani 1 1 d . U . . .
O5 O 0.4376(4) 0.8500(3) 0.3444(2) 0.0312(7) Uani 1 1 d . U . . .
O6 O 0.3103(5) 0.6311(3) 0.4003(2) 0.0394(8) Uani 1 1 d . U . . .
O7 O 0.4365(6) 0.3543(5) 0.3414(4) 0.0667(12) Uani 1 1 d . U . . .
H7A H 0.427460 0.283449 0.287454 0.100 Uiso 1 1 d R U . . .
H7B H 0.505750 0.341192 0.391457 0.100 Uiso 1 1 d R U . . .
O8 O 0.6980(5) 1.1585(4) 0.4210(3) 0.0473(9) Uani 1 1 d . U . . .
H8A H 0.788416 1.145148 0.384857 0.071 Uiso 1 1 d R U . . .
H8B H 0.738896 1.240133 0.467662 0.071 Uiso 1 1 d R U . . .
O9 O 0.7237(5) 0.9072(4) 0.5352(2) 0.0374(8) Uani 1 1 d . U . . .
H9A H 0.730297 0.820671 0.502817 0.056 Uiso 1 1 d R U . . .
H9B H 0.774799 0.923952 0.598784 0.056 Uiso 1 1 d R U . . .
O10 O 0.3886(16) -0.0026(15) -0.0049(11) 0.238(6) Uani 1 1 d . U . . .
H10D H 0.279661 -0.029379 -0.037365 0.285 Uiso 1 1 d R U . . .
H10E H 0.381410 0.032262 0.061005 0.285 Uiso 1 1 d R U . . .
O11 O 0.4772(17) 0.1146(13) 0.2004(7) 0.192(4) Uani 1 1 d . U . . .
H11A H 0.430111 0.038999 0.230964 0.230 Uiso 1 1 d R U . . .
H11B H 0.594911 0.127479 0.206114 0.230 Uiso 1 1 d R U . . .
C1 C 0.0504(7) -0.0563(5) -0.2268(3) 0.0305(9) Uani 1 1 d . U . . .
C2 C 0.0890(6) 0.1150(4) -0.2174(3) 0.0253(8) Uani 1 1 d . U . . .
C3 C 0.0865(6) 0.1837(4) -0.3065(3) 0.0233(8) Uani 1 1 d . U . . .
H3 H 0.055128 0.123220 -0.374674 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1304(6) 0.3421(4) -0.2951(3) 0.0208(8) Uani 1 1 d . U . . .
C5 C 0.1730(6) 0.4317(4) -0.1928(3) 0.0215(8) Uani 1 1 d . U . . .
H5 H 0.199826 0.537528 -0.184999 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1761(6) 0.3655(4) -0.1018(3) 0.0224(8) Uani 1 1 d . U . . .
C7 C 0.1349(6) 0.2072(5) -0.1154(3) 0.0277(9) Uani 1 1 d . U . . .
H7 H 0.137889 0.161628 -0.055389 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1324(6) 0.4190(4) -0.3910(3) 0.0220(8) Uani 1 1 d . U . . .
C9 C 0.2268(6) 0.4617(4) 0.0072(3) 0.0232(8) Uani 1 1 d . U . . .
C10 C 0.3333(7) 0.6148(5) 0.0241(3) 0.0315(9) Uani 1 1 d . U . . .
H10A H 0.375362 0.661131 -0.033980 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3761(6) 0.6973(5) 0.1278(3) 0.0305(9) Uani 1 1 d . U . . .
H16 H 0.444816 0.800154 0.140001 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3157(6) 0.6258(4) 0.2131(3) 0.0217(8) Uani 1 1 d . U . . .
C13 C 0.1691(6) 0.4012(4) 0.0984(3) 0.0240(8) Uani 1 1 d . U . . .
H18 H 0.094394 0.300157 0.088592 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3580(6) 0.7089(4) 0.3284(3) 0.0245(8) Uani 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 O9 2.142(3) 2_676 ?
Mn1 O9 2.142(3) . ?
Mn1 O5 2.164(3) . ?
Mn1 O5 2.164(3) 2_676 ?
Mn1 O8 2.166(3) . ?
Mn1 O8 2.166(3) 2_676 ?
Mn2 O4 2.156(3) 2_565 ?
Mn2 O6 2.183(3) . ?
Mn2 O3 2.185(3) 1_556 ?
Mn2 O2 2.187(3) 2 ?
Mn2 O7 2.223(4) . ?
Mn2 N1 2.280(3) . ?
N1 C13 1.333(5) . ?
N1 C12 1.339(5) . ?
O1 C1 1.232(6) . ?
O2 C1 1.258(5) . ?
O3 C8 1.260(5) . ?
O4 C8 1.251(5) . ?
O5 C14 1.252(5) . ?
O6 C14 1.251(5) . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8500 . ?
O8 H8A 0.8500 . ?
O8 H8B 0.8500 . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8500 . ?
O10 O10 1.65(2) 2_655 ?
O10 H10D 0.8500 . ?
O10 H10E 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8500 . ?
C1 C2 1.512(5) . ?
C2 C3 1.385(5) . ?
C2 C7 1.396(5) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 C8 1.503(5) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(6) . ?
C6 C9 1.485(5) . ?
C7 H7 0.9300 . ?
C9 C13 1.392(5) . ?
C9 C10 1.394(6) . ?
C10 C11 1.381(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(6) . ?
C11 H16 0.9300 . ?
C12 C14 1.510(5) . ?
C13 H18 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
O9 Mn1 O9 180.0 2_676 . ?
O9 Mn1 O5 89.93(12) 2_676 . ?
O9 Mn1 O5 90.07(12) . . ?
O9 Mn1 O5 90.07(12) 2_676 2_676 ?
O9 Mn1 O5 89.93(12) . 2_676 ?
O5 Mn1 O5 180.0 . 2_676 ?
O9 Mn1 O8 92.52(14) 2_676 . ?
O9 Mn1 O8 87.48(14) . . ?
O5 Mn1 O8 86.02(12) . . ?
O5 Mn1 O8 93.98(12) 2_676 . ?
O9 Mn1 O8 87.48(14) 2_676 2_676 ?
O9 Mn1 O8 92.52(14) . 2_676 ?
O5 Mn1 O8 93.98(12) . 2_676 ?
O5 Mn1 O8 86.02(12) 2_676 2_676 ?
O8 Mn1 O8 180.0 . 2_676 ?
O4 Mn2 O6 88.58(13) 2_565 . ?
O4 Mn2 O3 91.26(11) 2_565 1_556 ?
O6 Mn2 O3 93.09(11) . 1_556 ?
O4 Mn2 O2 99.28(12) 2_565 2 ?
O6 Mn2 O2 172.03(14) . 2 ?
O3 Mn2 O2 85.44(11) 1_556 2 ?
O4 Mn2 O7 172.62(15) 2_565 . ?
O6 Mn2 O7 84.15(16) . . ?
O3 Mn2 O7 87.89(14) 1_556 . ?
O2 Mn2 O7 87.96(15) 2 . ?
O4 Mn2 N1 96.30(11) 2_565 . ?
O6 Mn2 N1 73.35(11) . . ?
O3 Mn2 N1 164.24(12) 1_556 . ?
O2 Mn2 N1 106.85(11) 2 . ?
O7 Mn2 N1 82.84(14) . . ?
C13 N1 C12 118.0(3) . . ?
C13 N1 Mn2 128.2(2) . . ?
C12 N1 Mn2 113.8(2) . . ?
C1 O2 Mn2 131.6(3) . 2 ?
C8 O3 Mn2 133.0(3) . 1_554 ?
C8 O4 Mn2 131.3(3) . 2_565 ?
C14 O5 Mn1 125.5(2) . . ?
C14 O6 Mn2 119.7(2) . . ?
Mn2 O7 H7A 107.1 . . ?
Mn2 O7 H7B 126.4 . . ?
H7A O7 H7B 108.4 . . ?
Mn1 O8 H8A 129.6 . . ?
Mn1 O8 H8B 105.7 . . ?
H8A O8 H8B 108.2 . . ?
Mn1 O9 H9A 122.8 . . ?
Mn1 O9 H9B 121.0 . . ?
H9A O9 H9B 108.6 . . ?
O10 O10 H10D 153.4 2_655 . ?
O10 O10 H10E 97.0 2_655 . ?
H10D O10 H10E 108.9 . . ?
H11A O11 H11B 105.2 . . ?
O1 C1 O2 123.0(4) . . ?
O1 C1 C2 118.9(4) . . ?
O2 C1 C2 118.0(4) . . ?
C3 C2 C7 119.0(4) . . ?
C3 C2 C1 122.3(3) . . ?
C7 C2 C1 118.7(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 C8 121.5(3) . . ?
C5 C4 C8 119.1(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 C9 120.5(3) . . ?
C5 C6 C9 121.0(3) . . ?
C6 C7 C2 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
O4 C8 O3 124.1(3) . . ?
O4 C8 C4 118.7(3) . . ?
O3 C8 C4 117.1(3) . . ?
C13 C9 C10 116.6(3) . . ?
C13 C9 C6 120.7(3) . . ?
C10 C9 C6 122.6(3) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H16 120.3 . . ?
C10 C11 H16 120.3 . . ?
N1 C12 C11 122.2(3) . . ?
N1 C12 C14 115.7(3) . . ?
C11 C12 C14 122.1(3) . . ?
N1 C13 C9 124.2(3) . . ?
N1 C13 H18 117.9 . . ?
C9 C13 H18 117.9 . . ?
O6 C14 O5 125.3(3) . . ?
O6 C14 C12 117.2(3) . . ?
O5 C14 C12 117.5(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
Mn2 O2 C1 O1 13.5(8) 2 . . . ?
Mn2 O2 C1 C2 -170.8(3) 2 . . . ?
O1 C1 C2 C3 156.1(5) . . . . ?
O2 C1 C2 C3 -19.7(7) . . . . ?
O1 C1 C2 C7 -21.7(7) . . . . ?
O2 C1 C2 C7 162.5(4) . . . . ?
C7 C2 C3 C4 0.5(7) . . . . ?
C1 C2 C3 C4 -177.2(4) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C2 C3 C4 C8 178.7(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C8 C4 C5 C6 -178.9(4) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C4 C5 C6 C9 178.3(4) . . . . ?
C5 C6 C7 C2 -0.8(7) . . . . ?
C9 C6 C7 C2 -179.3(4) . . . . ?
C3 C2 C7 C6 0.6(7) . . . . ?
C1 C2 C7 C6 178.4(4) . . . . ?
Mn2 O4 C8 O3 107.9(4) 2_565 . . . ?
Mn2 O4 C8 C4 -73.7(4) 2_565 . . . ?
Mn2 O3 C8 O4 -11.6(7) 1_554 . . . ?
Mn2 O3 C8 C4 169.9(3) 1_554 . . . ?
C3 C4 C8 O4 153.1(4) . . . . ?
C5 C4 C8 O4 -26.7(6) . . . . ?
C3 C4 C8 O3 -28.4(6) . . . . ?
C5 C4 C8 O3 151.8(4) . . . . ?
C7 C6 C9 C13 -24.2(6) . . . . ?
C5 C6 C9 C13 157.3(4) . . . . ?
C7 C6 C9 C10 155.6(4) . . . . ?
C5 C6 C9 C10 -22.8(7) . . . . ?
C13 C9 C10 C11 0.1(7) . . . . ?
C6 C9 C10 C11 -179.7(4) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?
C13 N1 C12 C11 -0.8(6) . . . . ?
Mn2 N1 C12 C11 175.9(3) . . . . ?
C13 N1 C12 C14 178.4(4) . . . . ?
Mn2 N1 C12 C14 -4.9(4) . . . . ?
C10 C11 C12 N1 -1.0(7) . . . . ?
C10 C11 C12 C14 179.8(4) . . . . ?
C12 N1 C13 C9 2.5(6) . . . . ?
Mn2 N1 C13 C9 -173.7(3) . . . . ?
C10 C9 C13 N1 -2.1(7) . . . . ?
C6 C9 C13 N1 177.7(4) . . . . ?
Mn2 O6 C14 O5 175.4(3) . . . . ?
Mn2 O6 C14 C12 -4.5(5) . . . . ?
Mn1 O5 C14 O6 -3.8(7) . . . . ?
Mn1 O5 C14 C12 176.1(3) . . . . ?
N1 C12 C14 O6 6.4(6) . . . . ?
C11 C12 C14 O6 -174.4(4) . . . . ?
N1 C12 C14 O5 -173.6(4) . . . . ?
C11 C12 C14 O5 5.7(6) . . . . ?

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
O11 H11B O1 0.85 2.34 3.143(12) 157.5 2_655 yes
O11 H11A O5 0.85 2.45 3.241(12) 155.2 1_545 yes
O10 H10E O11 0.85 1.84 2.628(15) 154.4 . yes
O10 H10D O1 0.85 1.81 2.599(11) 154.1 . yes
O9 H9B O2 0.85 2.06 2.769(4) 140.9 1_666 yes
O9 H9A O3 0.85 1.91 2.709(4) 154.9 2_665 yes
O8 H8B O6 0.85 1.99 2.737(4) 146.6 2_676 yes
O8 H8A O2 0.85 2.08 2.926(5) 171.4 2_665 yes
O7 H7B O8 0.85 2.56 3.245(6) 138.2 1_545 yes
O7 H7A O11 0.85 1.89 2.695(10) 158.7 . yes

_refine_diff_density_max         0.945
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.108



####################################################################### 
# 
# 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_exp_10202
_database_code_depnum_ccdc_archive 'CCDC 2053175'
loop_
_audit_author_name
_audit_author_address
'Chuancong Zhou'
;LiaoCheng University
China
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-07-07 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            'C14 H17 Mn1.50 N O11.50'
_chemical_formula_weight         465.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 '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                   6.8023(7)
_cell_length_b                   9.1613(8)
_cell_length_c                   14.8193(15)
_cell_angle_alpha                103.790(8)
_cell_angle_beta                 100.798(8)
_cell_angle_gamma                101.414(8)
_cell_volume                     852.05(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1474
_cell_measurement_theta_min      5.1320
_cell_measurement_theta_max      71.4340

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             475
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.821
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5020
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.140
_diffrn_reflns_theta_max         67.247
_diffrn_reflns_theta_full        67.247
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3038
_reflns_number_gt                2355
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    diamond
_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)+(0.1072P)²+2.1566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3038
_refine_ls_number_parameters     259
_refine_ls_number_restraints     696
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2101
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.055
_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 0.500000 1.000000 0.000000 0.0126(3) Uani 1 2 d S U P . .
Mn2 Mn 0.30483(17) 0.55766(11) 0.19560(7) 0.0233(3) Uani 1 1 d . U . . .
N1 N 0.5269(8) 0.7736(5) 0.3113(3) 0.0148(10) Uani 1 1 d . U . . .
O1 O 0.6743(9) 0.5633(5) 0.6879(4) 0.0396(13) Uani 1 1 d . U . . .
O2 O 0.8507(7) 0.7037(5) 0.8303(3) 0.0207(9) Uani 1 1 d . U . . .
O3 O 1.1530(7) 1.2846(5) 0.8839(3) 0.0274(11) Uani 1 1 d . U . . .
O4 O 0.9719(7) 1.3786(5) 0.7818(3) 0.0225(10) Uani 1 1 d . U . . .
O5 O 0.5319(7) 0.9881(4) 0.1424(3) 0.0194(9) Uani 1 1 d . U . . .
O6 O 0.3661(7) 0.7438(5) 0.1263(3) 0.0214(9) Uani 1 1 d . U . . .
O9 O 0.5196(9) 0.4738(5) 0.1202(4) 0.0434(14) Uani 1 1 d . U . . .
H9B H 0.634555 0.488893 0.159858 0.065 Uiso 1 1 d R U . . .
H9D H 0.537355 0.522953 0.079198 0.065 Uiso 1 1 d R U . . .
O10 O 0.0524(15) 0.4706(10) 0.0365(6) 0.028(2) Uani 0.5 1 d . U P . .
H10B H 0.028111 0.559360 0.041806 0.034 Uiso 0.5 1 d R U P . .
H10C H -0.014459 0.434500 -0.021954 0.034 Uiso 0.5 1 d R U P . .
O7 O 0.7473(7) 0.8813(5) -0.0088(3) 0.0251(10) Uani 1 1 d . U . . .
H7B H 0.741176 0.819379 0.025753 0.038 Uiso 1 1 d R U . . .
H7C H 0.732496 0.830169 -0.066687 0.038 Uiso 1 1 d R U . . .
O8 O 0.2741(7) 0.7693(5) -0.0592(3) 0.0248(10) Uani 1 1 d . U . . .
H8B H 0.152029 0.780980 -0.064125 0.037 Uiso 1 1 d R U . . .
H8D H 0.296149 0.713840 -0.021705 0.037 Uiso 1 1 d R U . . .
O11 O 0.2001(19) 0.5558(14) 0.6717(9) 0.145(4) Uani 1 1 d . U . . .
H11C H 0.112619 0.497330 0.690227 0.174 Uiso 1 1 d R U . . .
H11A H 0.317039 0.534840 0.682327 0.174 Uiso 1 1 d R U . . .
O12 O 0.864(2) 0.4355(15) 0.5245(10) 0.180(5) Uani 1 1 d . U . . .
H12C H 0.761148 0.454106 0.546034 0.216 Uiso 1 1 d R U . . .
H12D H 0.842218 0.438376 0.466654 0.216 Uiso 1 1 d R U . . .
C1 C 0.7803(10) 0.6914(7) 0.7437(4) 0.0196(12) Uani 1 1 d . U . . .
C2 C 0.8182(9) 0.8310(6) 0.7067(4) 0.0167(12) Uani 1 1 d . U . . .
C3 C 0.9155(9) 0.9768(6) 0.7720(4) 0.0147(11) Uani 1 1 d . U . . .
H3 H 0.965814 0.986730 0.836547 0.018 Uiso 1 1 calc R U . . .
C4 C 0.9352(9) 1.1070(6) 0.7380(4) 0.0132(11) Uani 1 1 d . U . . .
C5 C 0.8647(9) 1.0912(6) 0.6422(4) 0.0142(11) Uani 1 1 d . U . . .
H5 H 0.877370 1.179562 0.621009 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7744(9) 0.9453(6) 0.5758(4) 0.0127(11) Uani 1 1 d . U . . .
C7 C 0.7482(9) 0.8151(6) 0.6102(4) 0.0174(12) Uani 1 1 d . U . . .
H7A H 0.683159 0.717148 0.567841 0.021 Uiso 1 1 calc R U . . .
C8 C 1.0262(9) 1.2669(6) 0.8064(4) 0.0148(11) Uani 1 1 d . U . . .
C9 C 0.7057(9) 0.9298(6) 0.4716(4) 0.0131(11) Uani 1 1 d . U . . .
C10 C 0.7459(9) 1.0582(7) 0.4362(4) 0.0176(12) Uani 1 1 d . U . . .
H10A H 0.819756 1.154624 0.478070 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6780(9) 1.0440(6) 0.3402(4) 0.0146(11) Uani 1 1 d . U . . .
H11 H 0.705176 1.129275 0.316568 0.017 Uiso 1 1 calc R U . . .
C12 C 0.5678(9) 0.8988(6) 0.2799(4) 0.0130(11) Uani 1 1 d . U . . .
C13 C 0.5946(10) 0.7896(7) 0.4035(4) 0.0195(12) Uani 1 1 d . U . . .
H13 H 0.566393 0.701589 0.424595 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4823(9) 0.8760(6) 0.1742(4) 0.0131(11) Uani 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 O5 2.112(4) . ?
Mn1 O5 2.112(4) 2_675 ?
Mn1 O7 2.184(4) 2_675 ?
Mn1 O7 2.184(4) . ?
Mn1 O8 2.219(4) . ?
Mn1 O8 2.219(4) 2_675 ?
Mn2 O4 2.139(4) 2_676 ?
Mn2 O9 2.149(5) . ?
Mn2 O6 2.203(4) . ?
Mn2 O1 2.261(5) 2_666 ?
Mn2 N1 2.316(5) . ?
Mn2 O2 2.325(4) 2_666 ?
N1 C13 1.321(8) . ?
N1 C12 1.336(7) . ?
O1 C1 1.249(8) . ?
O2 C1 1.252(7) . ?
O3 C8 1.254(7) . ?
O4 C8 1.263(7) . ?
O5 C14 1.242(7) . ?
O6 C14 1.264(7) . ?
O10 O10 1.452(17) 2_565 ?
C1 C2 1.503(8) . ?
C2 C7 1.383(8) . ?
C2 C3 1.397(8) . ?
C3 C4 1.394(8) . ?
C4 C5 1.373(8) . ?
C4 C8 1.502(7) . ?
C5 C6 1.397(8) . ?
C6 C7 1.398(8) . ?
C6 C9 1.491(8) . ?
C9 C13 1.397(8) . ?
C9 C10 1.398(8) . ?
C10 C11 1.377(8) . ?
C11 C12 1.384(8) . ?
C12 C14 1.513(8) . ?

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
O5 Mn1 O5 180.0 . 2_675 ?
O5 Mn1 O7 92.18(17) . 2_675 ?
O5 Mn1 O7 87.81(17) 2_675 2_675 ?
O5 Mn1 O7 87.82(17) . . ?
O5 Mn1 O7 92.18(17) 2_675 . ?
O7 Mn1 O7 180.00(19) 2_675 . ?
O5 Mn1 O8 92.61(16) . . ?
O5 Mn1 O8 87.39(16) 2_675 . ?
O7 Mn1 O8 91.74(17) 2_675 . ?
O7 Mn1 O8 88.26(17) . . ?
O5 Mn1 O8 87.39(16) . 2_675 ?
O5 Mn1 O8 92.61(16) 2_675 2_675 ?
O7 Mn1 O8 88.26(17) 2_675 2_675 ?
O7 Mn1 O8 91.74(17) . 2_675 ?
O8 Mn1 O8 180.0 . 2_675 ?
O4 Mn2 O9 159.2(2) 2_676 . ?
O4 Mn2 O6 89.13(17) 2_676 . ?
O9 Mn2 O6 82.07(19) . . ?
O4 Mn2 O1 93.8(2) 2_676 2_666 ?
O9 Mn2 O1 101.3(2) . 2_666 ?
O6 Mn2 O1 158.76(17) . 2_666 ?
O4 Mn2 N1 95.07(17) 2_676 . ?
O9 Mn2 N1 100.21(19) . . ?
O6 Mn2 N1 72.74(16) . . ?
O1 Mn2 N1 86.04(17) 2_666 . ?
O4 Mn2 O2 91.50(16) 2_676 2_666 ?
O9 Mn2 O2 85.08(17) . 2_666 ?
O6 Mn2 O2 144.68(15) . 2_666 ?
O1 Mn2 O2 56.37(16) 2_666 2_666 ?
N1 Mn2 O2 142.20(16) . 2_666 ?
C13 N1 C12 118.5(5) . . ?
C13 N1 Mn2 127.6(4) . . ?
C12 N1 Mn2 113.5(4) . . ?
C1 O1 Mn2 93.4(4) . 2_666 ?
C1 O2 Mn2 90.3(3) . 2_666 ?
C8 O4 Mn2 122.7(4) . 2_676 ?
C14 O5 Mn1 130.8(4) . . ?
C14 O6 Mn2 120.3(4) . . ?
O1 C1 O2 120.0(6) . . ?
O1 C1 C2 119.6(6) . . ?
O2 C1 C2 120.4(5) . . ?
C7 C2 C3 121.0(5) . . ?
C7 C2 C1 120.1(5) . . ?
C3 C2 C1 118.9(5) . . ?
C4 C3 C2 118.4(5) . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 C8 119.2(5) . . ?
C3 C4 C8 120.3(5) . . ?
C4 C5 C6 121.5(5) . . ?
C5 C6 C7 118.1(5) . . ?
C5 C6 C9 120.8(5) . . ?
C7 C6 C9 121.1(5) . . ?
C2 C7 C6 120.4(5) . . ?
O3 C8 O4 123.0(5) . . ?
O3 C8 C4 119.5(5) . . ?
O4 C8 C4 117.4(5) . . ?
C13 C9 C10 115.6(5) . . ?
C13 C9 C6 123.2(5) . . ?
C10 C9 C6 121.2(5) . . ?
C11 C10 C9 121.0(5) . . ?
C10 C11 C12 118.0(5) . . ?
N1 C12 C11 122.6(5) . . ?
N1 C12 C14 116.7(5) . . ?
C11 C12 C14 120.7(5) . . ?
N1 C13 C9 124.3(5) . . ?
O5 C14 O6 125.9(5) . . ?
O5 C14 C12 117.5(5) . . ?
O6 C14 C12 116.6(5) . . ?

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
Mn2 O1 C1 O2 0.7(7) 2_666 . . . ?
Mn2 O1 C1 C2 -177.8(5) 2_666 . . . ?
Mn2 O2 C1 O1 -0.7(7) 2_666 . . . ?
Mn2 O2 C1 C2 177.8(5) 2_666 . . . ?
O1 C1 C2 C7 -4.4(9) . . . . ?
O2 C1 C2 C7 177.0(6) . . . . ?
O1 C1 C2 C3 172.4(6) . . . . ?
O2 C1 C2 C3 -6.2(9) . . . . ?
C7 C2 C3 C4 1.8(9) . . . . ?
C1 C2 C3 C4 -175.0(5) . . . . ?
C2 C3 C4 C5 -1.5(9) . . . . ?
C2 C3 C4 C8 176.0(5) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C8 C4 C5 C6 -178.5(5) . . . . ?
C4 C5 C6 C7 3.1(9) . . . . ?
C4 C5 C6 C9 -177.8(5) . . . . ?
C3 C2 C7 C6 0.3(9) . . . . ?
C1 C2 C7 C6 177.1(5) . . . . ?
C5 C6 C7 C2 -2.7(9) . . . . ?
C9 C6 C7 C2 178.1(5) . . . . ?
Mn2 O4 C8 O3 -96.6(6) 2_676 . . . ?
Mn2 O4 C8 C4 84.4(6) 2_676 . . . ?
C5 C4 C8 O3 -155.0(6) . . . . ?
C3 C4 C8 O3 27.5(8) . . . . ?
C5 C4 C8 O4 24.1(8) . . . . ?
C3 C4 C8 O4 -153.5(6) . . . . ?
C5 C6 C9 C13 -172.8(6) . . . . ?
C7 C6 C9 C13 6.4(9) . . . . ?
C5 C6 C9 C10 5.8(8) . . . . ?
C7 C6 C9 C10 -175.0(6) . . . . ?
C13 C9 C10 C11 0.2(9) . . . . ?
C6 C9 C10 C11 -178.5(5) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C13 N1 C12 C11 0.0(9) . . . . ?
Mn2 N1 C12 C11 172.6(4) . . . . ?
C13 N1 C12 C14 -178.4(5) . . . . ?
Mn2 N1 C12 C14 -5.8(6) . . . . ?
C10 C11 C12 N1 -0.4(9) . . . . ?
C10 C11 C12 C14 177.9(5) . . . . ?
C12 N1 C13 C9 0.6(9) . . . . ?
Mn2 N1 C13 C9 -170.9(4) . . . . ?
C10 C9 C13 N1 -0.7(9) . . . . ?
C6 C9 C13 N1 178.0(5) . . . . ?
Mn1 O5 C14 O6 -13.1(9) . . . . ?
Mn1 O5 C14 C12 166.9(4) . . . . ?
Mn2 O6 C14 O5 178.1(4) . . . . ?
Mn2 O6 C14 C12 -2.0(7) . . . . ?
N1 C12 C14 O5 -174.7(5) . . . . ?
C11 C12 C14 O5 7.0(8) . . . . ?
N1 C12 C14 O6 5.4(8) . . . . ?
C11 C12 C14 O6 -173.0(5) . . . . ?

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
O12 H12D O11 0.85 2.03 2.880(19) 178.2 2_666 yes
O12 H12C O1 0.85 2.34 3.051(16) 141.7 . yes
O11 H11A O1 0.85 2.38 3.175(14) 156.9 . yes
O11 H11C O4 0.85 2.17 2.987(12) 160.6 1_445 yes
O8 H8D O6 0.85 2.09 2.778(6) 137.3 . yes
O8 H8B O2 0.85 2.20 2.901(6) 139.5 1_454 yes
O7 H7C O2 0.85 2.08 2.839(6) 149.2 1_554 yes
O7 H7B O3 0.85 1.93 2.734(6) 156.5 2_776 yes
O10 H10C O6 0.85 2.58 3.276(10) 140.2 2_565 yes
O10 H10C O3 0.85 2.33 2.773(10) 112.8 1_444 yes
O10 H10B O3 0.85 2.29 2.995(10) 141.0 2_676 yes
O9 H9D O3 0.85 2.34 2.833(7) 117.2 2_776 yes
O9 H9B O4 0.85 2.60 3.352(7) 148.9 2_776 yes
O9 H9B O4 0.85 2.60 3.352(7) 148.9 2_776 yes
O9 H9D O3 0.85 2.34 2.833(7) 117.2 2_776 yes
O10 H10B O3 0.85 2.29 2.995(10) 141.0 2_676 yes
O10 H10C O3 0.85 2.33 2.773(10) 112.8 1_444 yes
O10 H10C O6 0.85 2.58 3.276(10) 140.2 2_565 yes
O7 H7B O3 0.85 1.93 2.734(6) 156.5 2_776 yes
O7 H7C O2 0.85 2.08 2.839(6) 149.2 1_554 yes
O8 H8B O2 0.85 2.20 2.901(6) 139.5 1_454 yes
O8 H8D O6 0.85 2.09 2.778(6) 137.3 . yes
O11 H11C O4 0.85 2.17 2.987(12) 160.6 1_445 yes
O11 H11A O1 0.85 2.38 3.175(14) 156.9 . yes
O12 H12C O1 0.85 2.34 3.051(16) 141.7 . yes
O12 H12D O11 0.85 2.03 2.880(19) 178.2 2_666 yes

_refine_diff_density_max         0.937
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.156



