# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_90K
_database_code_depnum_ccdc_archive 'CCDC 1446778'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Mn2 N2 O12'
_chemical_formula_weight         470.16

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.5477(2)
_cell_length_b                   15.2820(3)
_cell_length_c                   13.6085(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.060(2)
_cell_angle_gamma                90
_cell_volume                     1777.61(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(4)
_cell_measurement_reflns_used    6099
_cell_measurement_theta_min      2.6640
_cell_measurement_theta_max      29.2120

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.484
_exptl_absorpt_correction_T_min  0.90922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.905
_oxdiff_exptl_absorpt_empirical_full_max 1.113
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      90.0(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            10570
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.666
_diffrn_reflns_theta_max         29.551
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3860
_reflns_number_gt                3638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.874
_reflns_Friedel_fraction_full    0.993

_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0220P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.404(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3860
_refine_ls_number_parameters     239
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0539
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.033
_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
Mn1 Mn 0.21792(8) 0.83650(2) 0.98797(5) 0.00698(10) Uani 1 1 d . . . . .
Mn2 Mn 0.21761(8) 0.50143(4) 0.73529(5) 0.00732(10) Uani 1 1 d . . . . .
O1 O 0.3053(3) 0.93129(17) 0.88103(18) 0.0110(6) Uani 1 1 d . . . . .
O2 O 0.1371(3) 0.94165(18) 1.08493(17) 0.0109(6) Uani 1 1 d . . . . .
O3 O 0.3089(3) 0.73669(17) 0.88980(18) 0.0118(6) Uani 1 1 d . . . . .
O4 O 0.1319(3) 0.74154(17) 1.09681(18) 0.0121(6) Uani 1 1 d . . . . .
O5 O 0.4469(3) 0.83260(16) 1.0514(2) 0.0129(6) Uani 1 1 d . . . . .
O6 O -0.0030(3) 0.83214(15) 0.9091(2) 0.0120(6) Uani 1 1 d . . . . .
O7 O 0.4414(3) 0.49016(16) 0.66053(19) 0.0120(6) Uani 1 1 d . . . . .
O8 O 0.3222(3) 0.60573(17) 0.81995(18) 0.0142(6) Uani 1 1 d . . . . .
O9 O -0.0077(3) 0.50869(16) 0.80788(19) 0.0121(6) Uani 1 1 d . . . . .
O10 O 0.1084(3) 0.39475(16) 0.65239(17) 0.0119(6) Uani 1 1 d . . . . .
O11 O 0.1351(3) 0.59806(19) 0.6329(2) 0.0159(6) Uani 1 1 d . . . . .
O12 O 0.2959(3) 0.39509(17) 0.83302(18) 0.0114(6) Uani 1 1 d . . . . .
C1 C 0.2475(5) 0.6663(2) 0.8598(3) 0.0116(9) Uani 1 1 d . . . . .
H1 H 0.1402 0.6592 0.8679 0.014 Uiso 1 1 calc R U . . .
C2 C 0.1781(5) 0.6640(2) 1.1051(3) 0.0105(9) Uani 1 1 d . . . . .
H2 H 0.2708 0.6488 1.0739 0.013 Uiso 1 1 calc R U . . .
C3 C -0.0716(4) 0.8965(2) 0.8729(3) 0.0103(7) Uani 1 1 d . . . . .
H3 H -0.0202 0.9501 0.8757 0.012 Uiso 1 1 calc R U . . .
C4 C 0.4962(4) 0.8791(2) 1.1192(3) 0.0122(8) Uani 1 1 d . . . . .
H4 H 0.4229 0.8989 1.1644 0.015 Uiso 1 1 calc R U . . .
C5 C -0.0030(4) 0.9458(2) 1.1147(3) 0.0110(7) Uani 1 1 d . . . . .
H5 H -0.0685 0.8986 1.1019 0.013 Uiso 1 1 calc R U . . .
C6 C 0.4394(4) 0.9649(2) 0.8777(3) 0.0137(8) Uani 1 1 d . . . . .
H6 H 0.5046 0.9564 0.9317 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2079(4) 0.8175(2) 0.6368(2) 0.0140(8) Uani 1 1 d . . . . .
H11A H 0.0953 0.8186 0.6454 0.017 Uiso 1 1 calc R U . . .
H11B H 0.2496 0.7702 0.6765 0.017 Uiso 1 1 calc R U . . .
C12 C 0.2454(4) 0.8006(2) 0.5291(2) 0.0128(6) Uani 1 1 d D . . . .
H12A H 0.3575 0.8051 0.5198 0.015 Uiso 1 1 calc R U . . .
H12B H 0.2145 0.7413 0.5125 0.015 Uiso 1 1 calc R U . . .
C13 C 0.1641(4) 0.8635(2) 0.4598(2) 0.0138(7) Uani 1 1 d D U . . .
H13A H 0.1987 0.9225 0.4747 0.017 Uiso 1 1 calc R U . . .
H13B H 0.0523 0.8609 0.4715 0.017 Uiso 1 1 calc R U . . .
C14 C 0.1942(4) 0.8452(2) 0.3511(3) 0.0145(8) Uani 1 1 d D . . . .
H14A H 0.1537 0.8932 0.3120 0.017 Uiso 1 1 calc R U . . .
H14B H 0.3061 0.8415 0.3399 0.017 Uiso 1 1 calc R U . . .
N1 N 0.1183(3) 0.76175(17) 0.31921(19) 0.0113(5) Uani 1 1 d . . . . .
H1A H 0.1755 0.7166 0.3397 0.017 Uiso 1 1 calc R U . . .
H1B H 0.1114 0.7607 0.2539 0.017 Uiso 1 1 calc R U . . .
H1C H 0.0229 0.7583 0.3449 0.017 Uiso 1 1 calc R U . . .
N2 N 0.2757(3) 0.90242(17) 0.67138(19) 0.0112(5) Uani 1 1 d . . . . .
H2A H 0.2292 0.9465 0.6400 0.017 Uiso 1 1 calc R U . . .
H2B H 0.3779 0.9034 0.6589 0.017 Uiso 1 1 calc R U . . .
H2C H 0.2604 0.9079 0.7357 0.017 Uiso 1 1 calc 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
Mn1 O5 2.138(3) . ?
Mn1 O6 2.170(3) . ?
Mn1 O3 2.173(3) . ?
Mn1 O1 2.187(3) . ?
Mn1 O2 2.192(3) . ?
Mn1 O4 2.202(3) . ?
Mn2 O11 2.148(3) . ?
Mn2 O8 2.159(3) . ?
Mn2 O9 2.170(2) . ?
Mn2 O7 2.176(2) . ?
Mn2 O10 2.190(2) . ?
Mn2 O12 2.203(3) . ?
O1 C6 1.257(5) . ?
O2 C5 1.267(4) . ?
O3 C1 1.264(4) . ?
O4 C2 1.255(4) . ?
O5 C4 1.237(5) . ?
O6 C3 1.246(4) . ?
O7 C5 1.254(4) 4_564 ?
O8 C1 1.250(4) . ?
O9 C6 1.248(4) 3_445 ?
O10 C2 1.255(4) 2_564 ?
O11 C4 1.251(4) 4_464 ?
O12 C3 1.255(4) 3_545 ?
C1 H1 0.9300 . ?
C2 O10 1.255(4) 2_565 ?
C2 H2 0.9300 . ?
C3 O12 1.255(4) 3_455 ?
C3 H3 0.9300 . ?
C4 O11 1.251(4) 4_565 ?
C4 H4 0.9300 . ?
C5 O7 1.254(4) 4_465 ?
C5 H5 0.9300 . ?
C6 O9 1.248(4) 3 ?
C6 H6 0.9300 . ?
C11 N2 1.496(4) . ?
C11 C12 1.523(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.528(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.494(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?

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 O6 173.29(11) . . ?
O5 Mn1 O3 84.24(10) . . ?
O6 Mn1 O3 89.26(10) . . ?
O5 Mn1 O1 88.45(10) . . ?
O6 Mn1 O1 89.42(10) . . ?
O3 Mn1 O1 86.11(10) . . ?
O5 Mn1 O2 93.85(10) . . ?
O6 Mn1 O2 92.56(10) . . ?
O3 Mn1 O2 176.88(10) . . ?
O1 Mn1 O2 91.37(7) . . ?
O5 Mn1 O4 90.99(10) . . ?
O6 Mn1 O4 91.16(10) . . ?
O3 Mn1 O4 94.12(7) . . ?
O1 Mn1 O4 179.38(12) . . ?
O2 Mn1 O4 88.38(10) . . ?
O11 Mn2 O8 88.47(10) . . ?
O11 Mn2 O9 88.29(10) . . ?
O8 Mn2 O9 94.93(9) . . ?
O11 Mn2 O7 92.19(10) . . ?
O8 Mn2 O7 86.83(10) . . ?
O9 Mn2 O7 178.18(12) . . ?
O11 Mn2 O10 92.23(11) . . ?
O8 Mn2 O10 178.68(11) . . ?
O9 Mn2 O10 83.97(9) . . ?
O7 Mn2 O10 94.25(9) . . ?
O11 Mn2 O12 175.88(13) . . ?
O8 Mn2 O12 95.62(11) . . ?
O9 Mn2 O12 91.79(9) . . ?
O7 Mn2 O12 87.60(10) . . ?
O10 Mn2 O12 83.69(9) . . ?
C6 O1 Mn1 127.5(2) . . ?
C5 O2 Mn1 122.0(3) . . ?
C1 O3 Mn1 130.3(2) . . ?
C2 O4 Mn1 125.3(2) . . ?
C4 O5 Mn1 126.5(2) . . ?
C3 O6 Mn1 125.4(3) . . ?
C5 O7 Mn2 120.4(2) 4_564 . ?
C1 O8 Mn2 124.6(3) . . ?
C6 O9 Mn2 130.0(2) 3_445 . ?
C2 O10 Mn2 126.4(3) 2_564 . ?
C4 O11 Mn2 126.7(2) 4_464 . ?
C3 O12 Mn2 121.4(2) 3_545 . ?
O8 C1 O3 123.9(4) . . ?
O8 C1 H1 118.0 . . ?
O3 C1 H1 118.0 . . ?
O10 C2 O4 124.9(4) 2_565 . ?
O10 C2 H2 117.6 2_565 . ?
O4 C2 H2 117.6 . . ?
O6 C3 O12 125.5(3) . 3_455 ?
O6 C3 H3 117.3 . . ?
O12 C3 H3 117.3 3_455 . ?
O5 C4 O11 126.3(3) . 4_565 ?
O5 C4 H4 116.9 . . ?
O11 C4 H4 116.9 4_565 . ?
O7 C5 O2 124.0(4) 4_465 . ?
O7 C5 H5 118.0 4_465 . ?
O2 C5 H5 118.0 . . ?
O9 C6 O1 125.4(4) 3 . ?
O9 C6 H6 117.3 3 . ?
O1 C6 H6 117.3 . . ?
N2 C11 C12 111.6(3) . . ?
N2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 113.2(3) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 114.1(3) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N1 C14 C13 111.3(3) . . ?
N1 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 N1 H1A 109.5 . . ?
C14 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C14 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?

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
N1 H1A O12 0.89 2.00 2.843(4) 158.7 2_564
N1 H1B O4 0.89 2.17 3.045(3) 169.2 1_554
N1 H1C O3 0.89 1.93 2.817(3) 172.6 4_464
N2 H2A O2 0.89 2.03 2.908(4) 171.3 2_574
N2 H2A O7 0.89 2.57 3.160(4) 124.9 3_455
N2 H2B O10 0.89 1.98 2.859(3) 170.4 3
N2 H2C O1 0.89 2.04 2.897(4) 160.1 .

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_160K
_database_code_depnum_ccdc_archive 'CCDC 1446779'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Mn2 N2 O12'
_chemical_formula_weight         470.16

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.5542(2)
_cell_length_b                   15.2990(3)
_cell_length_c                   13.6149(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.100(2)
_cell_angle_gamma                90
_cell_volume                     1781.79(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    159.99(17)
_cell_measurement_reflns_used    5956
_cell_measurement_theta_min      2.6550
_cell_measurement_theta_max      29.1870

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_T_min  0.89649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.908
_oxdiff_exptl_absorpt_empirical_full_max 1.056
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      159.99(17)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            10639
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         29.525
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3880
_reflns_number_gt                3596
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.879
_reflns_Friedel_fraction_full    0.994

_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0274P)²+0.6330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3880
_refine_ls_number_parameters     239
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.039
_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
Mn1 Mn 0.21810(9) 0.83626(3) 0.98788(6) 0.01024(10) Uani 1 1 d . . . . .
Mn2 Mn 0.21742(9) 0.50159(4) 0.73544(6) 0.01082(10) Uani 1 1 d . . . . .
O1 O 0.3060(3) 0.93136(19) 0.8811(2) 0.0161(7) Uani 1 1 d . . . . .
O2 O 0.1362(3) 0.9409(2) 1.0848(2) 0.0167(7) Uani 1 1 d . . . . .
O3 O 0.3095(3) 0.7366(2) 0.8895(2) 0.0183(7) Uani 1 1 d . . . . .
O4 O 0.1315(3) 0.7406(2) 1.0957(2) 0.0182(7) Uani 1 1 d . . . . .
O5 O 0.4460(4) 0.83246(18) 1.0523(2) 0.0201(8) Uani 1 1 d . . . . .
O6 O -0.0023(4) 0.83264(17) 0.9084(2) 0.0180(7) Uani 1 1 d . . . . .
O7 O 0.4412(3) 0.49117(18) 0.6605(2) 0.0173(7) Uani 1 1 d . . . . .
O8 O 0.3215(4) 0.60616(19) 0.8203(2) 0.0224(7) Uani 1 1 d . . . . .
O9 O -0.0070(3) 0.50812(18) 0.8085(2) 0.0173(7) Uani 1 1 d . . . . .
O10 O 0.1085(3) 0.39488(19) 0.6523(2) 0.0186(7) Uani 1 1 d . . . . .
O11 O 0.1343(4) 0.5980(2) 0.6335(2) 0.0253(8) Uani 1 1 d . . . . .
O12 O 0.2966(3) 0.39531(19) 0.8327(2) 0.0168(7) Uani 1 1 d . . . . .
C1 C 0.2482(6) 0.6671(2) 0.8601(3) 0.0165(10) Uani 1 1 d . . . . .
H1 H 0.1410 0.6603 0.8686 0.020 Uiso 1 1 calc R U . . .
C2 C 0.1772(6) 0.6635(3) 1.1048(3) 0.0153(10) Uani 1 1 d . . . . .
H2 H 0.2699 0.6482 1.0737 0.018 Uiso 1 1 calc R U . . .
C3 C -0.0706(5) 0.8966(3) 0.8729(3) 0.0166(9) Uani 1 1 d . . . . .
H3 H -0.0196 0.9502 0.8761 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4968(5) 0.8799(3) 1.1190(3) 0.0181(9) Uani 1 1 d . . . . .
H4 H 0.4233 0.9014 1.1631 0.022 Uiso 1 1 calc R U . . .
C5 C -0.0036(5) 0.9451(3) 1.1148(3) 0.0148(8) Uani 1 1 d . . . . .
H5 H -0.0691 0.8980 1.1021 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4392(5) 0.9650(3) 0.8783(3) 0.0188(9) Uani 1 1 d . . . . .
H6 H 0.5034 0.9572 0.9328 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2072(5) 0.8182(3) 0.6366(3) 0.0231(9) Uani 1 1 d . . . . .
H11A H 0.0946 0.8195 0.6450 0.028 Uiso 1 1 calc R U . . .
H11B H 0.2482 0.7708 0.6765 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2450(4) 0.8005(3) 0.5287(3) 0.0234(8) Uani 1 1 d D . . . .
H12A H 0.3570 0.8050 0.5192 0.028 Uiso 1 1 calc R U . . .
H12B H 0.2139 0.7413 0.5123 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1639(4) 0.8631(3) 0.4604(3) 0.0251(8) Uani 1 1 d D U . . .
H13A H 0.1976 0.9221 0.4757 0.030 Uiso 1 1 calc R U . . .
H13B H 0.0521 0.8600 0.4716 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1963(5) 0.8446(3) 0.3515(3) 0.0242(10) Uani 1 1 d D . . . .
H14A H 0.1573 0.8927 0.3120 0.029 Uiso 1 1 calc R U . . .
H14B H 0.3082 0.8403 0.3412 0.029 Uiso 1 1 calc R U . . .
N1 N 0.1193(3) 0.7614(2) 0.3194(2) 0.0173(6) Uani 1 1 d . . . . .
H1A H 0.1738 0.7160 0.3419 0.026 Uiso 1 1 calc R U . . .
H1B H 0.1159 0.7594 0.2541 0.026 Uiso 1 1 calc R U . . .
H1C H 0.0226 0.7593 0.3431 0.026 Uiso 1 1 calc R U . . .
N2 N 0.2750(3) 0.90266(19) 0.6714(2) 0.0174(6) Uani 1 1 d . . . . .
H2A H 0.2291 0.9468 0.6399 0.026 Uiso 1 1 calc R U . . .
H2B H 0.3772 0.9034 0.6593 0.026 Uiso 1 1 calc R U . . .
H2C H 0.2592 0.9082 0.7356 0.026 Uiso 1 1 calc 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
Mn1 O5 2.136(4) . ?
Mn1 O6 2.172(3) . ?
Mn1 O3 2.176(3) . ?
Mn1 O2 2.191(3) . ?
Mn1 O1 2.191(3) . ?
Mn1 O4 2.203(3) . ?
Mn2 O11 2.146(3) . ?
Mn2 O8 2.163(3) . ?
Mn2 O9 2.167(3) . ?
Mn2 O7 2.177(3) . ?
Mn2 O10 2.192(3) . ?
Mn2 O12 2.202(3) . ?
O1 C6 1.251(5) . ?
O2 C5 1.266(5) . ?
O3 C1 1.251(5) . ?
O4 C2 1.248(5) . ?
O5 C4 1.240(5) . ?
O6 C3 1.238(5) . ?
O7 C5 1.250(5) 4_564 ?
O8 C1 1.248(5) . ?
O9 C6 1.247(5) 3_445 ?
O10 C2 1.250(5) 2_564 ?
O11 C4 1.239(5) 4_464 ?
O12 C3 1.260(5) 3_545 ?
C1 H1 0.9300 . ?
C2 O10 1.250(5) 2_565 ?
C2 H2 0.9300 . ?
C3 O12 1.260(5) 3_455 ?
C3 H3 0.9300 . ?
C4 O11 1.239(5) 4_565 ?
C4 H4 0.9300 . ?
C5 O7 1.250(5) 4_465 ?
C5 H5 0.9300 . ?
C6 O9 1.247(5) 3 ?
C6 H6 0.9300 . ?
C11 N2 1.493(5) . ?
C11 C12 1.530(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.535(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.498(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?

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 O6 173.60(14) . . ?
O5 Mn1 O3 84.52(11) . . ?
O6 Mn1 O3 89.34(11) . . ?
O5 Mn1 O2 93.79(11) . . ?
O6 Mn1 O2 92.27(11) . . ?
O3 Mn1 O2 177.05(11) . . ?
O5 Mn1 O1 88.63(12) . . ?
O6 Mn1 O1 89.16(11) . . ?
O3 Mn1 O1 86.10(12) . . ?
O2 Mn1 O1 91.45(8) . . ?
O5 Mn1 O4 90.95(12) . . ?
O6 Mn1 O4 91.25(11) . . ?
O3 Mn1 O4 93.82(8) . . ?
O2 Mn1 O4 88.62(11) . . ?
O1 Mn1 O4 179.58(14) . . ?
O11 Mn2 O8 88.38(12) . . ?
O11 Mn2 O9 88.43(12) . . ?
O8 Mn2 O9 94.85(11) . . ?
O11 Mn2 O7 92.15(11) . . ?
O8 Mn2 O7 86.76(12) . . ?
O9 Mn2 O7 178.31(14) . . ?
O11 Mn2 O10 92.23(13) . . ?
O8 Mn2 O10 178.68(14) . . ?
O9 Mn2 O10 84.00(11) . . ?
O7 Mn2 O10 94.39(11) . . ?
O11 Mn2 O12 175.86(16) . . ?
O8 Mn2 O12 95.73(12) . . ?
O9 Mn2 O12 91.69(11) . . ?
O7 Mn2 O12 87.61(11) . . ?
O10 Mn2 O12 83.67(10) . . ?
C6 O1 Mn1 127.4(3) . . ?
C5 O2 Mn1 122.4(3) . . ?
C1 O3 Mn1 129.9(3) . . ?
C2 O4 Mn1 126.1(3) . . ?
C4 O5 Mn1 127.0(3) . . ?
C3 O6 Mn1 125.6(3) . . ?
C5 O7 Mn2 120.7(3) 4_564 . ?
C1 O8 Mn2 125.3(3) . . ?
C6 O9 Mn2 130.9(3) 3_445 . ?
C2 O10 Mn2 126.8(3) 2_564 . ?
C4 O11 Mn2 127.1(3) 4_464 . ?
C3 O12 Mn2 121.7(3) 3_545 . ?
O8 C1 O3 124.3(4) . . ?
O8 C1 H1 117.9 . . ?
O3 C1 H1 117.9 . . ?
O4 C2 O10 125.4(4) . 2_565 ?
O4 C2 H2 117.3 . . ?
O10 C2 H2 117.3 2_565 . ?
O6 C3 O12 125.5(4) . 3_455 ?
O6 C3 H3 117.2 . . ?
O12 C3 H3 117.2 3_455 . ?
O11 C4 O5 127.3(4) 4_565 . ?
O11 C4 H4 116.3 4_565 . ?
O5 C4 H4 116.3 . . ?
O7 C5 O2 124.0(4) 4_465 . ?
O7 C5 H5 118.0 4_465 . ?
O2 C5 H5 118.0 . . ?
O9 C6 O1 125.4(4) 3 . ?
O9 C6 H6 117.3 3 . ?
O1 C6 H6 117.3 . . ?
N2 C11 C12 112.0(3) . . ?
N2 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.6(3) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 113.3(3) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C13 111.0(3) . . ?
N1 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 N1 H1A 109.5 . . ?
C14 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C14 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?

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

N1 H1A O12 0.89 2.01 2.842(4) 156.2 2_564
N1 H1B O4 0.89 2.18 3.065(4) 172.1 1_554
N1 H1C O3 0.89 1.93 2.820(4) 175.5 4_464
N2 H2A O2 0.89 2.04 2.919(4) 171.4 2_574
N2 H2A O7 0.89 2.57 3.164(4) 124.7 3_455
N2 H2B O10 0.89 1.99 2.868(4) 170.9 3
N2 H2C O1 0.89 2.05 2.900(4) 159.4 .

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_345K
_database_code_depnum_ccdc_archive 'CCDC 1446780'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Mn2 N2 O12'
_chemical_formula_weight         470.16

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.5685(2)
_cell_length_b                   15.3292(4)
_cell_length_c                   13.6602(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.226(2)
_cell_angle_gamma                90
_cell_volume                     1794.24(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    345(2)
_cell_measurement_reflns_used    4140
_cell_measurement_theta_min      3.0500
_cell_measurement_theta_max      28.1940

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_min  0.96510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      345(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            8647
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.982
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.680
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2751
_reflns_number_gt                2323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0319P)²+1.1099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.38(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     246
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      1.000
_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
Mn1 Mn 0.2184(2) 0.83558(4) 0.98772(12) 0.01931(16) Uani 1 1 d . . . . .
Mn2 Mn 0.2163(2) 0.50213(8) 0.73527(12) 0.01995(16) Uani 1 1 d . . . . .
O1 O 0.3111(7) 0.9303(4) 0.8826(4) 0.0361(15) Uani 1 1 d . . . . .
O2 O 0.1339(7) 0.9392(4) 1.0850(4) 0.0314(14) Uani 1 1 d . . . . .
O3 O 0.3130(7) 0.7368(4) 0.8894(4) 0.0353(15) Uani 1 1 d . . . . .
O4 O 0.1312(7) 0.7380(4) 1.0919(4) 0.0378(16) Uani 1 1 d . . . . .
O5 O 0.4431(9) 0.8328(3) 1.0563(5) 0.0436(18) Uani 1 1 d . . . . .
O6 O 0.0015(8) 0.8342(3) 0.9058(5) 0.0375(16) Uani 1 1 d . . . . .
O7 O 0.4381(7) 0.4951(3) 0.6610(4) 0.0344(17) Uani 1 1 d . . . . .
O8 O 0.3196(7) 0.6085(4) 0.8172(4) 0.0437(17) Uani 1 1 d . . . . .
O9 O -0.0061(7) 0.5068(3) 0.8112(4) 0.0351(17) Uani 1 1 d . . . . .
O10 O 0.1092(7) 0.3947(4) 0.6524(4) 0.0406(16) Uani 1 1 d . . . . .
O11 O 0.1298(8) 0.5971(5) 0.6338(5) 0.0577(19) Uani 1 1 d . . . . .
O12 O 0.3013(6) 0.3968(4) 0.8307(4) 0.0335(14) Uani 1 1 d . . . . .
C1 C 0.2489(13) 0.6685(5) 0.8578(6) 0.035(2) Uani 1 1 d . . . . .
H1 H 0.1416 0.6629 0.8656 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1746(11) 0.6624(5) 1.1043(6) 0.027(2) Uani 1 1 d . . . . .
H2 H 0.2672 0.6466 1.0739 0.033 Uiso 1 1 calc R U . . .
C3 C -0.0677(11) 0.8977(6) 0.8709(6) 0.035(2) Uani 1 1 d . . . . .
H3 H -0.0175 0.9514 0.8750 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4978(11) 0.8799(6) 1.1190(6) 0.038(2) Uani 1 1 d . . . . .
H4 H 0.4253 0.9020 1.1630 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0058(10) 0.9421(5) 1.1148(5) 0.0313(19) Uani 1 1 d . . . . .
H5 H -0.0702 0.8947 1.1014 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4399(10) 0.9647(5) 0.8788(6) 0.0340(19) Uani 1 1 d . . . . .
H6 H 0.5036 0.9580 0.9335 0.041 Uiso 1 1 calc R U . . .
N1 N 0.1229(6) 0.7609(4) 0.3201(4) 0.0423(13) Uani 1 1 d . . . . .
H1A H 0.1764 0.7148 0.3413 0.063 Uiso 1 1 calc R U . . .
H1B H 0.1176 0.7598 0.2551 0.063 Uiso 1 1 calc R U . . .
H1C H 0.0269 0.7595 0.3447 0.063 Uiso 1 1 calc R U . . .
N2 N 0.2731(6) 0.9050(3) 0.6705(4) 0.0388(13) Uani 1 1 d . . . . .
H2A H 0.3759 0.9033 0.6617 0.058 Uiso 1 1 calc R U . . .
H2B H 0.2527 0.9111 0.7340 0.058 Uiso 1 1 calc R U . . .
H2C H 0.2332 0.9500 0.6377 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2025(13) 0.8231(6) 0.6343(6) 0.053(3) Uani 1 1 d D . . . .
H11A H 0.0899 0.8277 0.6392 0.063 Uiso 1 1 calc R U . . .
H11B H 0.2357 0.7756 0.6764 0.063 Uiso 1 1 calc R U . . .
C12 C 0.2447(11) 0.8010(6) 0.5292(5) 0.036(2) Uani 0.701(13) 1 d D . P . .
H12A H 0.3566 0.8065 0.5203 0.043 Uiso 0.701(13) 1 calc R U P . .
H12B H 0.2152 0.7413 0.5148 0.043 Uiso 0.701(13) 1 calc R U P . .
C13 C 0.1611(11) 0.8620(6) 0.4609(5) 0.034(2) Uani 0.701(13) 1 d D U P . .
H13A H 0.1903 0.9216 0.4760 0.040 Uiso 0.701(13) 1 calc R U P . .
H13B H 0.0493 0.8564 0.4703 0.040 Uiso 0.701(13) 1 calc R U P . .
C14 C 0.2019(13) 0.8415(5) 0.3521(6) 0.053(3) Uani 1 1 d D . . . .
H14A H 0.1693 0.8898 0.3108 0.064 Uiso 1 1 calc R U . . .
H14B H 0.3139 0.8347 0.3455 0.064 Uiso 1 1 calc R U . . .
C15 C 0.145(3) 0.8368(18) 0.5303(12) 0.047(5) Uiso 0.299(13) 1 d D . P . .
C16 C 0.266(3) 0.8387(18) 0.4549(12) 0.047(5) Uiso 0.299(13) 1 d D . P . .


_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 2.138(8) . ?
Mn1 O3 2.182(5) . ?
Mn1 O6 2.166(7) . ?
Mn1 O2 2.195(5) . ?
Mn1 O4 2.198(6) . ?
Mn1 O1 2.194(6) . ?
Mn2 O11 2.141(6) . ?
Mn2 O8 2.165(6) . ?
Mn2 O7 2.161(6) . ?
Mn2 O9 2.174(6) . ?
Mn2 O10 2.198(6) . ?
Mn2 O12 2.198(5) . ?
O1 C6 1.225(10) . ?
O2 C5 1.266(10) . ?
O3 C1 1.258(10) . ?
O4 C2 1.229(9) . ?
O5 C4 1.214(11) . ?
O6 C3 1.235(10) . ?
O7 C5 1.249(9) 4_564 ?
O8 C1 1.235(10) . ?
O9 C6 1.219(9) 3_445 ?
O10 C2 1.231(10) 2_564 ?
O11 C4 1.201(11) 4_464 ?
O12 C3 1.248(10) 3_545 ?
C1 H1 0.9300 . ?
C2 O10 1.231(10) 2_565 ?
C2 H2 0.9300 . ?
C3 O12 1.248(10) 3_455 ?
C3 H3 0.9300 . ?
C4 O11 1.201(11) 4_565 ?
C4 H4 0.9300 . ?
C5 O7 1.249(9) 4_465 ?
C5 H5 0.9300 . ?
C6 O9 1.219(9) 3 ?
C6 H6 0.9300 . ?
N1 C14 1.475(10) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C11 1.477(9) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C11 C12 1.521(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.501(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.561(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.465(13) . ?

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 O3 85.4(2) . . ?
O5 Mn1 O6 174.6(3) . . ?
O3 Mn1 O6 89.7(2) . . ?
O5 Mn1 O2 92.8(2) . . ?
O3 Mn1 O2 177.0(2) . . ?
O6 Mn1 O2 92.0(2) . . ?
O5 Mn1 O4 90.6(3) . . ?
O3 Mn1 O4 93.14(13) . . ?
O6 Mn1 O4 92.0(2) . . ?
O2 Mn1 O4 89.2(2) . . ?
O5 Mn1 O1 88.4(3) . . ?
O3 Mn1 O1 85.4(2) . . ?
O6 Mn1 O1 88.9(2) . . ?
O2 Mn1 O1 92.19(14) . . ?
O4 Mn1 O1 178.3(3) . . ?
O11 Mn2 O8 87.8(3) . . ?
O11 Mn2 O7 91.9(2) . . ?
O8 Mn2 O7 85.5(2) . . ?
O11 Mn2 O9 89.1(3) . . ?
O8 Mn2 O9 94.9(2) . . ?
O7 Mn2 O9 178.9(3) . . ?
O11 Mn2 O10 91.9(3) . . ?
O8 Mn2 O10 179.5(3) . . ?
O7 Mn2 O10 95.0(2) . . ?
O9 Mn2 O10 84.6(2) . . ?
O11 Mn2 O12 175.5(3) . . ?
O8 Mn2 O12 96.5(3) . . ?
O7 Mn2 O12 87.2(2) . . ?
O9 Mn2 O12 91.7(2) . . ?
O10 Mn2 O12 83.8(2) . . ?
C6 O1 Mn1 129.9(6) . . ?
C5 O2 Mn1 122.3(5) . . ?
C1 O3 Mn1 128.8(6) . . ?
C2 O4 Mn1 128.8(6) . . ?
C4 O5 Mn1 129.9(6) . . ?
C3 O6 Mn1 127.0(6) . . ?
C5 O7 Mn2 122.7(5) 4_564 . ?
C1 O8 Mn2 126.4(7) . . ?
C6 O9 Mn2 132.8(6) 3_445 . ?
C2 O10 Mn2 128.2(6) 2_564 . ?
C4 O11 Mn2 129.2(6) 4_464 . ?
C3 O12 Mn2 123.2(5) 3_545 . ?
O8 C1 O3 124.1(10) . . ?
O8 C1 H1 117.9 . . ?
O3 C1 H1 117.9 . . ?
O4 C2 O10 127.3(9) . 2_565 ?
O4 C2 H2 116.3 . . ?
O10 C2 H2 116.3 2_565 . ?
O6 C3 O12 126.2(8) . 3_455 ?
O6 C3 H3 116.9 . . ?
O12 C3 H3 116.9 3_455 . ?
O11 C4 O5 130.9(9) 4_565 . ?
O11 C4 H4 114.6 4_565 . ?
O5 C4 H4 114.6 . . ?
O2 C5 O7 123.8(8) . 4_465 ?
O2 C5 H5 118.1 . . ?
O7 C5 H5 118.1 4_465 . ?
O9 C6 O1 127.2(8) 3 . ?
O9 C6 H6 116.4 3 . ?
O1 C6 H6 116.4 . . ?
C14 N1 H1A 109.5 . . ?
C14 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C14 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C11 C12 114.0(7) . . ?
N2 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N2 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 109.5(7) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 111.0(7) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N1 C14 C13 110.2(7) . . ?
N1 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N1 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?

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

N1 H1A O12 0.89 2.02 2.863(7) 156.9 2_564
N1 H1B O4 0.89 2.26 3.138(8) 170.6 1_554
N1 H1C O3 0.89 1.93 2.823(8) 175.1 4_464
N2 H2A O10 0.89 2.01 2.895(9) 175.4 3
N2 H2B O1 0.89 2.11 2.939(8) 154.9 .
N2 H2C O2 0.89 2.03 2.912(8) 170.5 2_574

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_360K
_database_code_depnum_ccdc_archive 'CCDC 1446781'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Mn2 N2 O12'
_chemical_formula_weight         470.16

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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

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

_cell_length_a                   8.6962(2)
_cell_length_b                   8.6962(2)
_cell_length_c                   13.6572(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     894.44(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    360(2)
_cell_measurement_reflns_used    6106
_cell_measurement_theta_min      2.7300
_cell_measurement_theta_max      28.1630

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_min  0.84586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      360(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            9753
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         2.695
_diffrn_reflns_theta_max         28.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             739
_reflns_number_gt                675
_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, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         739
_refine_ls_number_parameters     44
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.225
_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
Mn1 Mn 0.6667 0.3333 0.2500 0.0259(3) Uani 1 6 d S T P . .
Mn2 Mn 1.0000 0.0000 0.0000 0.0250(3) Uani 1 6 d S T P . .
C1 C 0.8876(5) 0.2136(5) 0.1292(3) 0.0453(9) Uani 1 1 d . . . . .
H1 H 0.7949 0.1013 0.1453 0.054 Uiso 1 1 calc R U . . .
O1 O 0.8707(4) 0.3390(4) 0.1556(2) 0.0535(8) Uani 1 1 d . . . . .
O2 O 1.0120(3) 0.2179(4) 0.0841(2) 0.0468(7) Uani 1 1 d . . . . .
N1 N 0.3511(14) -0.4715(11) 0.0640(7) 0.053(2) Uiso 0.3333 1 d D . P A 1
H1A H 0.4444 -0.4749 0.0882 0.079 Uiso 0.3333 1 calc R U P A 1
H1B H 0.3664 -0.4488 0.0001 0.079 Uiso 0.3333 1 calc R U P A 1
H1C H 0.2533 -0.5759 0.0737 0.079 Uiso 0.3333 1 calc R U P A 1
C2 C 0.3333 -0.3333 0.1128(6) 0.084(3) Uani 1 3 d DS T P A 1
H2A H 0.2077 -0.3745 0.1203 0.101 Uiso 0.3333 1 calc R U P A 1
H2B H 0.3823 -0.2304 0.0701 0.101 Uiso 0.3333 1 calc R U P A 1
C3 C 0.4194(12) -0.2744(19) 0.2113(5) 0.056(3) Uiso 0.3333 1 d D . P A 1
H3A H 0.4652 -0.3513 0.2306 0.067 Uiso 0.3333 1 calc R U P A 1
H3B H 0.5200 -0.1551 0.2050 0.067 Uiso 0.3333 1 calc R U P A 1


_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 2.174(3) 4_665 ?
Mn1 O1 2.174(3) 6 ?
Mn1 O1 2.174(3) 3_665 ?
Mn1 O1 2.174(3) 2_655 ?
Mn1 O1 2.174(3) 5_655 ?
Mn1 O1 2.174(3) . ?
Mn2 O2 2.173(2) . ?
Mn2 O2 2.173(2) 7_755 ?
Mn2 O2 2.173(2) 9_545 ?
Mn2 O2 2.173(2) 3_765 ?
Mn2 O2 2.173(2) 2_645 ?
Mn2 O2 2.173(2) 8_665 ?
C1 O1 1.225(4) . ?
C1 O2 1.229(4) . ?
N1 C2 1.4484(10) . ?
C2 C3 1.499(8) . ?
C3 C3 1.445(9) 5_655 ?

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 O1 88.43(12) 4_665 6 ?
O1 Mn1 O1 90.03(16) 4_665 3_665 ?
O1 Mn1 O1 177.77(15) 6 3_665 ?
O1 Mn1 O1 177.77(15) 4_665 2_655 ?
O1 Mn1 O1 93.15(16) 6 2_655 ?
O1 Mn1 O1 88.43(12) 3_665 2_655 ?
O1 Mn1 O1 88.43(12) 4_665 5_655 ?
O1 Mn1 O1 88.43(12) 6 5_655 ?
O1 Mn1 O1 93.15(16) 3_665 5_655 ?
O1 Mn1 O1 90.03(16) 2_655 5_655 ?
O1 Mn1 O1 93.15(16) 4_665 . ?
O1 Mn1 O1 90.03(16) 6 . ?
O1 Mn1 O1 88.43(12) 3_665 . ?
O1 Mn1 O1 88.43(12) 2_655 . ?
O1 Mn1 O1 177.77(15) 5_655 . ?
O2 Mn2 O2 180.0 . 7_755 ?
O2 Mn2 O2 85.35(11) . 9_545 ?
O2 Mn2 O2 94.65(11) 7_755 9_545 ?
O2 Mn2 O2 94.65(11) . 3_765 ?
O2 Mn2 O2 85.35(11) 7_755 3_765 ?
O2 Mn2 O2 180.00(16) 9_545 3_765 ?
O2 Mn2 O2 94.65(11) . 2_645 ?
O2 Mn2 O2 85.35(11) 7_755 2_645 ?
O2 Mn2 O2 85.35(11) 9_545 2_645 ?
O2 Mn2 O2 94.65(11) 3_765 2_645 ?
O2 Mn2 O2 85.35(11) . 8_665 ?
O2 Mn2 O2 94.65(11) 7_755 8_665 ?
O2 Mn2 O2 94.65(11) 9_545 8_665 ?
O2 Mn2 O2 85.35(11) 3_765 8_665 ?
O2 Mn2 O2 180.00(12) 2_645 8_665 ?
O1 C1 O2 128.0(4) . . ?
C1 O1 Mn1 127.9(3) . . ?
C1 O2 Mn2 125.5(2) . . ?
N1 C2 C3 117.0(6) . . ?
C3 C3 C2 115.6(10) 5_655 . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_298K
_database_code_depnum_ccdc_archive 'CCDC 1446782'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Mn2 N2 O12'
_chemical_formula_weight         470.16

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.5608(2)
_cell_length_b                   15.3339(3)
_cell_length_c                   13.6433(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.190(2)
_cell_angle_gamma                90
_cell_volume                     1790.98(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6551
_cell_measurement_theta_min      2.7400
_cell_measurement_theta_max      28.4360

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.473
_exptl_absorpt_correction_T_min  0.86247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_ambient_temperature      298(2)
_diffrn_reflns_number            9298
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3788
_reflns_number_gt                3599
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.997

_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, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0400P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.34(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3788
_refine_ls_number_parameters     239
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.108
_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
Mn1 Mn 0.21861(7) 0.83573(2) 0.98774(5) 0.01754(7) Uani 1 1 d . . . . .
Mn2 Mn 0.21677(7) 0.50202(3) 0.73566(5) 0.01820(7) Uani 1 1 d . . . . .
O1 O 0.3091(3) 0.93087(15) 0.88225(17) 0.0312(6) Uani 1 1 d . . . . .
O2 O 0.1342(2) 0.93931(15) 1.08489(17) 0.0291(6) Uani 1 1 d . . . . .
O3 O 0.3112(3) 0.73677(15) 0.88936(18) 0.0319(6) Uani 1 1 d . . . . .
O4 O 0.1302(3) 0.73843(15) 1.09299(18) 0.0342(6) Uani 1 1 d . . . . .
O5 O 0.4443(3) 0.83238(16) 1.0555(2) 0.0386(7) Uani 1 1 d . . . . .
O6 O 0.0009(3) 0.83416(14) 0.90597(19) 0.0327(6) Uani 1 1 d . . . . .
O7 O 0.4402(3) 0.49387(14) 0.66035(19) 0.0321(6) Uani 1 1 d . . . . .
O8 O 0.3193(3) 0.60731(16) 0.8193(2) 0.0415(7) Uani 1 1 d . . . . .
O9 O -0.0058(3) 0.50726(14) 0.81042(18) 0.0296(6) Uani 1 1 d . . . . .
O10 O 0.1082(3) 0.39464(16) 0.65235(17) 0.0329(6) Uani 1 1 d . . . . .
O11 O 0.1314(3) 0.59777(19) 0.6347(2) 0.0486(7) Uani 1 1 d . . . . .
O12 O 0.2998(2) 0.39617(15) 0.83123(18) 0.0299(6) Uani 1 1 d . . . . .
C1 C 0.2491(4) 0.6679(2) 0.8595(3) 0.0287(8) Uani 1 1 d . . . . .
H1 H 0.1419 0.6619 0.8681 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1750(4) 0.6626(2) 1.1047(2) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.2683 0.6470 1.0747 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0691(4) 0.8968(2) 0.8716(2) 0.0278(7) Uani 1 1 d . . . . .
H3 H -0.0193 0.9505 0.8760 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4967(4) 0.8806(2) 1.1194(2) 0.0330(8) Uani 1 1 d . . . . .
H4 H 0.4232 0.9039 1.1622 0.040 Uiso 1 1 calc R U . . .
C5 C -0.0046(4) 0.9429(2) 1.1150(2) 0.0257(7) Uani 1 1 d . . . . .
H5 H -0.0696 0.8955 1.1026 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4406(4) 0.9649(2) 0.8792(2) 0.0294(8) Uani 1 1 d . . . . .
H6 H 0.5044 0.9578 0.9340 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2028(5) 0.8218(3) 0.6363(3) 0.0432(10) Uani 1 1 d . . . . .
H11A H 0.0902 0.8255 0.6428 0.052 Uiso 1 1 calc R U . . .
H11B H 0.2389 0.7742 0.6775 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2437(5) 0.8015(3) 0.5284(3) 0.0526(11) Uani 1 1 d D . . . .
H12A H 0.3556 0.8065 0.5194 0.063 Uiso 1 1 calc R U . . .
H12B H 0.2137 0.7420 0.5133 0.063 Uiso 1 1 calc R U . . .
C13 C 0.1629(5) 0.8617(3) 0.4610(3) 0.0523(10) Uani 1 1 d D U . . .
H13A H 0.1936 0.9210 0.4764 0.063 Uiso 1 1 calc R U . . .
H13B H 0.0511 0.8570 0.4710 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1997(6) 0.8429(2) 0.3520(3) 0.0465(11) Uani 1 1 d D . . . .
H14A H 0.1634 0.8911 0.3118 0.056 Uiso 1 1 calc R U . . .
H14B H 0.3118 0.8376 0.3434 0.056 Uiso 1 1 calc R U . . .
N1 N 0.1223(3) 0.76116(19) 0.3200(2) 0.0334(7) Uani 1 1 d . . . . .
H1A H 0.1740 0.7156 0.3443 0.050 Uiso 1 1 calc R U . . .
H1B H 0.1220 0.7584 0.2549 0.050 Uiso 1 1 calc R U . . .
H1C H 0.0244 0.7604 0.3418 0.050 Uiso 1 1 calc R U . . .
N2 N 0.2737(3) 0.90418(18) 0.6710(2) 0.0322(6) Uani 1 1 d . . . . .
H2A H 0.2301 0.9489 0.6396 0.048 Uiso 1 1 calc R U . . .
H2B H 0.3758 0.9034 0.6592 0.048 Uiso 1 1 calc R U . . .
H2C H 0.2577 0.9098 0.7351 0.048 Uiso 1 1 calc 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
Mn1 O5 2.140(3) . ?
Mn1 O6 2.169(2) . ?
Mn1 O3 2.177(2) . ?
Mn1 O2 2.193(2) . ?
Mn1 O1 2.192(2) . ?
Mn1 O4 2.207(2) . ?
Mn2 O11 2.140(3) . ?
Mn2 O8 2.162(2) . ?
Mn2 O9 2.166(2) . ?
Mn2 O7 2.178(3) . ?
Mn2 O12 2.199(2) . ?
Mn2 O10 2.205(2) . ?
O1 C6 1.242(4) . ?
O2 C5 1.259(4) . ?
O3 C1 1.250(4) . ?
O4 C2 1.235(4) . ?
O5 C4 1.227(4) . ?
O6 C3 1.224(4) . ?
O7 C5 1.244(4) 4_564 ?
O8 C1 1.236(4) . ?
O9 C6 1.232(4) 3_445 ?
O10 C2 1.233(4) 2_564 ?
O11 C4 1.217(4) 4_464 ?
O12 C3 1.248(4) 3_545 ?
C1 H1 0.9300 . ?
C2 O10 1.233(4) 2_565 ?
C2 H2 0.9300 . ?
C3 O12 1.248(4) 3_455 ?
C3 H3 0.9300 . ?
C4 O11 1.217(4) 4_565 ?
C4 H4 0.9300 . ?
C5 O7 1.244(4) 4_465 ?
C5 H5 0.9300 . ?
C6 O9 1.232(4) 3 ?
C6 H6 0.9300 . ?
C11 N2 1.479(5) . ?
C11 C12 1.545(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.474(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.549(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.483(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?

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 O6 174.29(12) . . ?
O5 Mn1 O3 85.38(10) . . ?
O6 Mn1 O3 89.38(9) . . ?
O5 Mn1 O2 93.17(9) . . ?
O6 Mn1 O2 91.97(9) . . ?
O3 Mn1 O2 177.39(9) . . ?
O5 Mn1 O1 88.80(10) . . ?
O6 Mn1 O1 88.55(9) . . ?
O3 Mn1 O1 85.92(9) . . ?
O2 Mn1 O1 91.88(8) . . ?
O5 Mn1 O4 90.80(10) . . ?
O6 Mn1 O4 91.78(9) . . ?
O3 Mn1 O4 93.23(8) . . ?
O2 Mn1 O4 88.96(9) . . ?
O1 Mn1 O4 179.09(10) . . ?
O11 Mn2 O8 87.98(11) . . ?
O11 Mn2 O9 88.76(10) . . ?
O8 Mn2 O9 94.60(10) . . ?
O11 Mn2 O7 91.98(10) . . ?
O8 Mn2 O7 86.33(10) . . ?
O9 Mn2 O7 178.83(10) . . ?
O11 Mn2 O12 175.70(12) . . ?
O8 Mn2 O12 96.22(10) . . ?
O9 Mn2 O12 91.79(9) . . ?
O7 Mn2 O12 87.40(9) . . ?
O11 Mn2 O10 92.18(11) . . ?
O8 Mn2 O10 178.87(11) . . ?
O9 Mn2 O10 84.29(9) . . ?
O7 Mn2 O10 94.78(9) . . ?
O12 Mn2 O10 83.64(9) . . ?
C6 O1 Mn1 128.6(2) . . ?
C5 O2 Mn1 122.8(2) . . ?
C1 O3 Mn1 129.4(2) . . ?
C2 O4 Mn1 127.9(2) . . ?
C4 O5 Mn1 128.3(2) . . ?
C3 O6 Mn1 127.4(2) . . ?
C5 O7 Mn2 121.7(2) 4_564 . ?
C1 O8 Mn2 126.7(2) . . ?
C6 O9 Mn2 132.1(2) 3_445 . ?
C2 O10 Mn2 127.4(2) 2_564 . ?
C4 O11 Mn2 128.2(2) 4_464 . ?
C3 O12 Mn2 123.0(2) 3_545 . ?
O8 C1 O3 124.9(3) . . ?
O8 C1 H1 117.5 . . ?
O3 C1 H1 117.5 . . ?
O4 C2 O10 126.4(3) . 2_565 ?
O4 C2 H2 116.8 . . ?
O10 C2 H2 116.8 2_565 . ?
O6 C3 O12 127.0(3) . 3_455 ?
O6 C3 H3 116.5 . . ?
O12 C3 H3 116.5 3_455 . ?
O11 C4 O5 129.0(3) 4_565 . ?
O11 C4 H4 115.5 4_565 . ?
O5 C4 H4 115.5 . . ?
O7 C5 O2 123.8(3) 4_465 . ?
O7 C5 H5 118.1 4_465 . ?
O2 C5 H5 118.1 . . ?
O9 C6 O1 126.0(3) 3 . ?
O9 C6 H6 117.0 3 . ?
O1 C6 H6 117.0 . . ?
N2 C11 C12 112.5(3) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.2(3) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 112.7(3) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N1 C14 C13 110.3(3) . . ?
N1 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N1 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 N1 H1A 109.5 . . ?
C14 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C14 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?

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
N1 H1A O12 0.89 2.03 2.855(4) 153.2 2_564
N1 H1B O4 0.89 2.23 3.118(4) 174.5 1_554
N1 H1C O3 0.89 1.94 2.829(4) 178.0 4_464
N2 H2A O2 0.89 2.04 2.925(4) 172.2 2_574
N2 H2A O7 0.89 2.59 3.171(4) 123.5 3_455
N2 H2B O10 0.89 2.00 2.880(4) 171.6 3
N2 H2C O1 0.89 2.08 2.926(4) 158.7 .

_refine_diff_density_max         1.689
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.071



