# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1434500'
_audit_update_record             
;
2015-12-17 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Mn2 N O13.5'
_chemical_formula_weight         613.27

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   10.7074(3)
_cell_length_b                   28.5474(8)
_cell_length_c                   8.0000(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2445.35(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33633
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.427
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_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             5807
_reflns_number_gt                5528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Brucker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_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)+(0.0288P)²+1.6702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5807
_refine_ls_number_parameters     384
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.178
_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 0.16001(5) 0.15886(2) 1.28203(7) 0.02211(13) Uani 1 1 d . . . . .
Mn2 Mn 0.42466(5) 0.28752(2) 1.24050(8) 0.02311(13) Uani 1 1 d . . . . .
O1 O 0.1071(2) 0.14039(9) 1.0289(4) 0.0263(6) Uani 1 1 d . . . . .
O2 O 0.1245(2) 0.18659(10) 0.8079(4) 0.0319(6) Uani 1 1 d . . . . .
O3 O 0.3044(2) 0.20522(9) 1.1489(4) 0.0296(6) Uani 1 1 d . . . . .
O4 O 0.4807(3) 0.23437(10) 1.0546(4) 0.0307(7) Uani 1 1 d . . . . .
O5 O 0.6358(3) 0.16912(9) 0.4593(4) 0.0336(7) Uani 1 1 d . . . . .
O6 O 0.7336(2) 0.20161(8) 0.6751(4) 0.0269(6) Uani 1 1 d . . . . .
O7 O 0.9629(3) 0.17036(9) 0.5366(4) 0.0366(8) Uani 1 1 d . . . . .
O8 O 1.0157(3) 0.11216(10) 0.3745(5) 0.0400(8) Uani 1 1 d . . . . .
O9 O 0.0638(2) 0.22845(8) 1.2522(4) 0.0272(6) Uani 1 1 d D . . . .
H9A H 0.118(4) 0.2483(13) 1.279(6) 0.044(14) Uiso 1 1 d D . . . .
H9B H 0.023(5) 0.237(2) 1.166(6) 0.08(2) Uiso 1 1 d D . . . .
O10 O 0.2435(3) 0.18809(11) 1.4981(4) 0.0336(7) Uani 1 1 d D . . . .
H10A H 0.207(4) 0.1895(19) 1.589(5) 0.055(17) Uiso 1 1 d D . . . .
H10B H 0.310(3) 0.2029(16) 1.500(6) 0.043(15) Uiso 1 1 d D . . . .
O11 O 0.3705(3) 0.33378(12) 1.0383(4) 0.0378(7) Uani 1 1 d D . . . .
H11A H 0.333(4) 0.3212(19) 0.956(5) 0.07(2) Uiso 1 1 d D . . . .
H11B H 0.440(3) 0.3449(15) 1.005(5) 0.030(12) Uiso 1 1 d D . . . .
O12 O 0.4645(3) 0.23722(10) 1.4458(4) 0.0277(6) Uani 1 1 d D . . . .
H12A H 0.477(4) 0.2516(14) 1.535(4) 0.035(14) Uiso 1 1 d D . . . .
H12B H 0.519(5) 0.2161(17) 1.436(8) 0.09(2) Uiso 1 1 d D . . . .
O13 O 0.8852(16) 0.0571(5) 0.1268(16) 0.171(8) Uani 0.5 1 d . . P . .
O14 O 0.7530(4) 0.21819(17) 0.1935(6) 0.0703(13) Uani 1 1 d D . . . .
H14C H 0.719(5) 0.2018(18) 0.269(6) 0.065(19) Uiso 1 1 d D . . . .
H14B H 0.695(5) 0.232(3) 0.141(9) 0.12(3) Uiso 1 1 d D . . . .
N1 N 0.2954(3) 0.09760(10) 1.2790(5) 0.0308(7) Uani 1 1 d . . . . .
C1 C 0.1673(3) 0.15772(12) 0.9086(5) 0.0218(7) Uani 1 1 d . . . . .
C2 C 0.2990(3) 0.14029(12) 0.8767(5) 0.0219(7) Uani 1 1 d . . . . .
C3 C 0.4058(3) 0.16323(12) 0.9319(5) 0.0213(7) Uani 1 1 d . . . . .
C4 C 0.3954(3) 0.20350(12) 1.0528(5) 0.0216(7) Uani 1 1 d . . . . .
C5 C 0.5230(3) 0.14707(12) 0.8818(5) 0.0239(8) Uani 1 1 d . . . . .
H5A H 0.5942 0.1630 0.9165 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5353(3) 0.10762(11) 0.7809(5) 0.0238(8) Uani 1 1 d . . . . .
C7 C 0.4280(3) 0.08420(12) 0.7311(6) 0.0298(8) Uani 1 1 d . . . . .
H7A H 0.4345 0.0572 0.6665 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3106(3) 0.10080(12) 0.7769(6) 0.0308(9) Uani 1 1 d . . . . .
H8A H 0.2393 0.0853 0.7403 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6604(3) 0.08985(11) 0.7266(6) 0.0271(8) Uani 1 1 d . . . . .
C10 C 0.7437(3) 0.11801(11) 0.6355(5) 0.0206(7) Uani 1 1 d . . . . .
C11 C 0.7025(3) 0.16697(11) 0.5864(5) 0.0212(7) Uani 1 1 d . . . . .
C12 C 0.8564(3) 0.09925(12) 0.5779(6) 0.0271(8) Uani 1 1 d . . . . .
C13 C 0.9508(3) 0.12904(12) 0.4893(6) 0.0243(8) Uani 1 1 d . . . . .
C14 C 0.8854(4) 0.05269(15) 0.6105(8) 0.0490(14) Uani 1 1 d . . . . .
H14A H 0.9594 0.0400 0.5698 0.059 Uiso 1 1 calc R U . . .
C15 C 0.8048(5) 0.02519(14) 0.7033(9) 0.0631(19) Uani 1 1 d . . . . .
H15A H 0.8258 -0.0057 0.7277 0.076 Uiso 1 1 calc R U . . .
C16 C 0.6929(4) 0.04350(13) 0.7599(8) 0.0465(14) Uani 1 1 d . . . . .
H16A H 0.6387 0.0247 0.8209 0.056 Uiso 1 1 calc R U . . .
C17 C 0.4169(4) 0.10203(14) 1.3071(6) 0.0346(9) Uani 1 1 d . . . . .
H17A H 0.4475 0.1317 1.3324 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2544(4) 0.05472(13) 1.2405(8) 0.0446(12) Uani 1 1 d . . . . .
H18A H 0.1699 0.0508 1.2174 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5006(4) 0.06536(13) 1.3010(6) 0.0341(10) Uani 1 1 d . . . . .
H19A H 0.5851 0.0706 1.3202 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3310(4) 0.01595(13) 1.2332(8) 0.0454(12) Uani 1 1 d . . . . .
H20A H 0.2979 -0.0132 1.2064 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4574(3) 0.02060(12) 1.2660(6) 0.0301(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O10 2.118(3) . ?
Mn1 O1 2.168(3) . ?
Mn1 O8 2.171(3) 1_456 ?
Mn1 O9 2.251(2) . ?
Mn1 N1 2.272(3) . ?
Mn1 O3 2.297(3) . ?
Mn2 O11 2.167(3) . ?
Mn2 O6 2.176(3) 3_457 ?
Mn2 O7 2.189(3) 3_457 ?
Mn2 O4 2.208(3) . ?
Mn2 O12 2.223(3) . ?
Mn2 O2 2.297(3) 3_557 ?
O1 C1 1.260(5) . ?
O2 C1 1.240(5) . ?
O2 Mn2 2.297(3) 3_457 ?
O3 C4 1.242(4) . ?
O4 C4 1.269(4) . ?
O5 C11 1.244(5) . ?
O6 C11 1.262(4) . ?
O6 Mn2 2.176(3) 3_557 ?
O7 C13 1.246(4) . ?
O7 Mn2 2.189(3) 3_557 ?
O8 C13 1.249(5) . ?
O8 Mn1 2.171(3) 1_654 ?
O9 H9A 0.83(2) . ?
O9 H9B 0.85(2) . ?
O10 H10A 0.82(2) . ?
O10 H10B 0.83(2) . ?
O11 H11A 0.85(2) . ?
O11 H11B 0.85(2) . ?
O12 H12A 0.83(2) . ?
O12 H12B 0.85(2) . ?
O14 H14C 0.85(2) . ?
O14 H14B 0.85(3) . ?
N1 C17 1.326(5) . ?
N1 C18 1.337(5) . ?
C1 C2 1.517(5) . ?
C2 C8 1.387(5) . ?
C2 C3 1.389(5) . ?
C3 C5 1.396(5) . ?
C3 C4 1.507(5) . ?
C5 C6 1.392(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.388(5) . ?
C6 C9 1.497(5) . ?
C7 C8 1.392(5) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C16 1.394(5) . ?
C9 C10 1.405(5) . ?
C10 C12 1.399(5) . ?
C10 C11 1.517(5) . ?
C12 C14 1.390(5) . ?
C12 C13 1.499(5) . ?
C14 C15 1.383(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(6) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C19 1.379(5) . ?
C17 H17A 0.9300 . ?
C18 C20 1.379(5) . ?
C18 H18A 0.9300 . ?
C19 C21 1.387(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.386(5) . ?
C20 H20A 0.9300 . ?
C21 C21 1.488(7) 2_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
O10 Mn1 O1 165.66(11) . . ?
O10 Mn1 O8 105.31(13) . 1_456 ?
O1 Mn1 O8 89.02(12) . 1_456 ?
O10 Mn1 O9 86.10(12) . . ?
O1 Mn1 O9 89.78(11) . . ?
O8 Mn1 O9 104.63(11) 1_456 . ?
O10 Mn1 N1 92.45(13) . . ?
O1 Mn1 N1 88.25(12) . . ?
O8 Mn1 N1 89.13(12) 1_456 . ?
O9 Mn1 N1 166.07(11) . . ?
O10 Mn1 O3 82.38(11) . . ?
O1 Mn1 O3 83.29(10) . . ?
O8 Mn1 O3 172.31(13) 1_456 . ?
O9 Mn1 O3 75.55(9) . . ?
N1 Mn1 O3 90.52(11) . . ?
O11 Mn2 O6 83.88(11) . 3_457 ?
O11 Mn2 O7 108.87(13) . 3_457 ?
O6 Mn2 O7 81.08(11) 3_457 3_457 ?
O11 Mn2 O4 89.35(13) . . ?
O6 Mn2 O4 124.23(11) 3_457 . ?
O7 Mn2 O4 151.07(12) 3_457 . ?
O11 Mn2 O12 175.16(12) . . ?
O6 Mn2 O12 92.47(11) 3_457 . ?
O7 Mn2 O12 73.56(11) 3_457 . ?
O4 Mn2 O12 90.09(11) . . ?
O11 Mn2 O2 85.83(11) . 3_557 ?
O6 Mn2 O2 151.89(10) 3_457 3_557 ?
O7 Mn2 O2 77.65(12) 3_457 3_557 ?
O4 Mn2 O2 81.63(11) . 3_557 ?
O12 Mn2 O2 98.85(11) . 3_557 ?
C1 O1 Mn1 119.0(2) . . ?
C1 O2 Mn2 131.9(2) . 3_457 ?
C4 O3 Mn1 142.4(2) . . ?
C4 O4 Mn2 106.8(2) . . ?
C11 O6 Mn2 122.3(2) . 3_557 ?
C13 O7 Mn2 138.4(3) . 3_557 ?
C13 O8 Mn1 114.2(2) . 1_654 ?
Mn1 O9 H9A 105(3) . . ?
Mn1 O9 H9B 125(4) . . ?
H9A O9 H9B 111(4) . . ?
Mn1 O10 H10A 123(4) . . ?
Mn1 O10 H10B 125(3) . . ?
H10A O10 H10B 112(4) . . ?
Mn2 O11 H11A 117(4) . . ?
Mn2 O11 H11B 103(3) . . ?
H11A O11 H11B 109(4) . . ?
Mn2 O12 H12A 110(3) . . ?
Mn2 O12 H12B 122(5) . . ?
H12A O12 H12B 109(4) . . ?
H14C O14 H14B 107(4) . . ?
C17 N1 C18 116.7(3) . . ?
C17 N1 Mn1 123.4(3) . . ?
C18 N1 Mn1 119.9(2) . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C2 116.9(3) . . ?
O1 C1 C2 118.4(3) . . ?
C8 C2 C3 119.5(3) . . ?
C8 C2 C1 116.5(3) . . ?
C3 C2 C1 123.8(3) . . ?
C2 C3 C5 119.5(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C3 C4 120.2(3) . . ?
O3 C4 O4 122.0(3) . . ?
O3 C4 C3 119.0(3) . . ?
O4 C4 C3 119.0(3) . . ?
C6 C5 C3 121.2(3) . . ?
C6 C5 H5A 119.4 . . ?
C3 C5 H5A 119.4 . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 C9 119.6(3) . . ?
C5 C6 C9 121.8(3) . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C2 C8 C7 120.6(3) . . ?
C2 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C16 C9 C10 118.9(3) . . ?
C16 C9 C6 119.3(3) . . ?
C10 C9 C6 121.7(3) . . ?
C12 C10 C9 120.0(3) . . ?
C12 C10 C11 121.2(3) . . ?
C9 C10 C11 118.5(3) . . ?
O5 C11 O6 124.9(3) . . ?
O5 C11 C10 115.1(3) . . ?
O6 C11 C10 120.0(3) . . ?
C14 C12 C10 119.8(3) . . ?
C14 C12 C13 118.7(3) . . ?
C10 C12 C13 121.3(3) . . ?
O7 C13 O8 122.0(4) . . ?
O7 C13 C12 117.7(3) . . ?
O8 C13 C12 120.3(3) . . ?
C15 C14 C12 120.3(4) . . ?
C15 C14 H14A 119.9 . . ?
C12 C14 H14A 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C9 120.8(4) . . ?
C15 C16 H16A 119.6 . . ?
C9 C16 H16A 119.6 . . ?
N1 C17 C19 124.0(4) . . ?
N1 C17 H17A 118.0 . . ?
C19 C17 H17A 118.0 . . ?
N1 C18 C20 123.3(4) . . ?
N1 C18 H18A 118.3 . . ?
C20 C18 H18A 118.3 . . ?
C17 C19 C21 119.3(4) . . ?
C17 C19 H19A 120.3 . . ?
C21 C19 H19A 120.3 . . ?
C18 C20 C21 119.8(4) . . ?
C18 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C20 C21 C19 116.9(3) . . ?
C20 C21 C21 121.5(4) . 2_655 ?
C19 C21 C21 121.6(4) . 2_655 ?

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 -11.2(6) 3_457 . . . ?
Mn2 O2 C1 C2 165.0(3) 3_457 . . . ?
Mn1 O1 C1 O2 -111.7(4) . . . . ?
Mn1 O1 C1 C2 72.1(4) . . . . ?
O2 C1 C2 C8 -89.8(4) . . . . ?
O1 C1 C2 C8 86.6(5) . . . . ?
O2 C1 C2 C3 85.8(5) . . . . ?
O1 C1 C2 C3 -97.8(4) . . . . ?
C8 C2 C3 C5 2.0(6) . . . . ?
C1 C2 C3 C5 -173.5(4) . . . . ?
C8 C2 C3 C4 -174.5(4) . . . . ?
C1 C2 C3 C4 10.1(5) . . . . ?
Mn1 O3 C4 O4 -152.6(3) . . . . ?
Mn1 O3 C4 C3 26.7(6) . . . . ?
Mn2 O4 C4 O3 -3.0(5) . . . . ?
Mn2 O4 C4 C3 177.8(3) . . . . ?
C2 C3 C4 O3 26.8(5) . . . . ?
C5 C3 C4 O3 -149.6(4) . . . . ?
C2 C3 C4 O4 -153.9(4) . . . . ?
C5 C3 C4 O4 29.6(5) . . . . ?
C2 C3 C5 C6 -1.7(6) . . . . ?
C4 C3 C5 C6 174.8(4) . . . . ?
C3 C5 C6 C7 -0.3(6) . . . . ?
C3 C5 C6 C9 -179.9(4) . . . . ?
C5 C6 C7 C8 2.0(6) . . . . ?
C9 C6 C7 C8 -178.5(4) . . . . ?
C3 C2 C8 C7 -0.4(6) . . . . ?
C1 C2 C8 C7 175.4(4) . . . . ?
C6 C7 C8 C2 -1.7(7) . . . . ?
C7 C6 C9 C16 -54.7(6) . . . . ?
C5 C6 C9 C16 124.8(5) . . . . ?
C7 C6 C9 C10 122.0(4) . . . . ?
C5 C6 C9 C10 -58.4(6) . . . . ?
C16 C9 C10 C12 0.8(7) . . . . ?
C6 C9 C10 C12 -176.0(4) . . . . ?
C16 C9 C10 C11 174.5(4) . . . . ?
C6 C9 C10 C11 -2.2(6) . . . . ?
Mn2 O6 C11 O5 -133.8(3) 3_557 . . . ?
Mn2 O6 C11 C10 48.1(4) 3_557 . . . ?
C12 C10 C11 O5 91.9(4) . . . . ?
C9 C10 C11 O5 -81.8(5) . . . . ?
C12 C10 C11 O6 -89.9(5) . . . . ?
C9 C10 C11 O6 96.5(4) . . . . ?
C9 C10 C12 C14 0.3(7) . . . . ?
C11 C10 C12 C14 -173.3(4) . . . . ?
C9 C10 C12 C13 -176.2(4) . . . . ?
C11 C10 C12 C13 10.2(6) . . . . ?
Mn2 O7 C13 O8 -157.1(3) 3_557 . . . ?
Mn2 O7 C13 C12 21.5(6) 3_557 . . . ?
Mn1 O8 C13 O7 5.0(5) 1_654 . . . ?
Mn1 O8 C13 C12 -173.6(3) 1_654 . . . ?
C14 C12 C13 O7 -140.8(5) . . . . ?
C10 C12 C13 O7 35.7(6) . . . . ?
C14 C12 C13 O8 37.9(7) . . . . ?
C10 C12 C13 O8 -145.6(4) . . . . ?
C10 C12 C14 C15 -1.6(9) . . . . ?
C13 C12 C14 C15 175.0(6) . . . . ?
C12 C14 C15 C16 1.9(10) . . . . ?
C14 C15 C16 C9 -0.9(10) . . . . ?
C10 C9 C16 C15 -0.5(8) . . . . ?
C6 C9 C16 C15 176.3(5) . . . . ?
C18 N1 C17 C19 -1.0(8) . . . . ?
Mn1 N1 C17 C19 -178.1(4) . . . . ?
C17 N1 C18 C20 1.6(9) . . . . ?
Mn1 N1 C18 C20 178.9(5) . . . . ?
N1 C17 C19 C21 -0.9(8) . . . . ?
N1 C18 C20 C21 -0.4(10) . . . . ?
C18 C20 C21 C19 -1.6(8) . . . . ?
C18 C20 C21 C21 177.6(4) . . . 2_655 ?
C17 C19 C21 C20 2.2(7) . . . . ?
C17 C19 C21 C21 -177.0(3) . . . 2_655 ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3



_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1434501'
_audit_update_record             
;
2015-12-17 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Mn2 N O13.5'
_chemical_formula_weight         626.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9630(4)
_cell_length_b                   10.7340(5)
_cell_length_c                   30.1664(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.4870(10)
_cell_angle_gamma                90
_cell_volume                     2578.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34458
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         28.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6281
_reflns_number_gt                5192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Brucker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.7807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6281
_refine_ls_number_parameters     395
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.03243(4) 0.45369(3) 0.16397(2) 0.02244(9) Uani 1 1 d . . . . .
Mn2 Mn -0.00901(4) 0.18632(3) 0.28595(2) 0.02285(9) Uani 1 1 d . . . . .
O1 O -0.22250(17) 0.50388(12) 0.14539(5) 0.0268(3) Uani 1 1 d . . . . .
O2 O -0.44286(18) 0.48763(13) 0.18968(5) 0.0323(3) Uani 1 1 d . . . . .
O3 O -0.10381(18) 0.30964(13) 0.20778(5) 0.0301(3) Uani 1 1 d . . . . .
O4 O -0.19677(18) 0.13371(13) 0.23537(5) 0.0293(3) Uani 1 1 d . . . . .
O5 O -0.57649(18) -0.12329(13) 0.20424(4) 0.0268(3) Uani 1 1 d . . . . .
O6 O -0.79550(18) -0.02694(14) 0.17363(5) 0.0329(3) Uani 1 1 d . . . . .
O7 O -0.7163(2) -0.35125(15) 0.17428(5) 0.0369(4) Uani 1 1 d . . . . .
O8 O -0.8771(2) -0.40475(15) 0.11827(5) 0.0388(4) Uani 1 1 d . . . . .
O9 O 0.24823(18) 0.37000(15) 0.19304(5) 0.0331(3) Uani 1 1 d D . . . .
H9A H 0.347(2) 0.398(2) 0.1947(9) 0.048(8) Uiso 1 1 d D . . . .
H9B H 0.238(3) 0.3034(18) 0.2061(9) 0.049(8) Uiso 1 1 d D . . . .
O10 O 0.00125(18) 0.54828(13) 0.22985(5) 0.0260(3) Uani 1 1 d D . . . .
H10A H 0.015(3) 0.4905(19) 0.2483(7) 0.036(7) Uiso 1 1 d D . . . .
H10B H -0.089(3) 0.585(2) 0.2395(9) 0.054(8) Uiso 1 1 d D . . . .
O11 O -0.2099(2) 0.24079(15) 0.33031(6) 0.0362(4) Uani 1 1 d D . . . .
H11A H -0.286(3) 0.278(2) 0.3168(9) 0.055(9) Uiso 1 1 d D . . . .
H11B H -0.243(3) 0.1732(18) 0.3412(9) 0.049(8) Uiso 1 1 d D . . . .
O12 O 0.19466(18) 0.14601(14) 0.23793(5) 0.0283(3) Uani 1 1 d D . . . .
H12A H 0.182(4) 0.092(2) 0.2180(8) 0.069(10) Uiso 1 1 d D . . . .
H12B H 0.281(3) 0.131(3) 0.2527(8) 0.052(8) Uiso 1 1 d D . . . .
O13 O 0.1394(10) 0.2705(9) -0.0717(2) 0.160(4) Uani 0.5 1 d . . P . .
O14 O -0.4396(3) 0.3592(2) 0.28017(8) 0.0701(7) Uani 1 1 d D . . . .
H14B H -0.395(4) 0.412(3) 0.2642(11) 0.104(15) Uiso 1 1 d D . . . .
H14C H -0.515(4) 0.389(3) 0.2963(10) 0.087(13) Uiso 1 1 d D . . . .
N1 N 0.0329(2) 0.31653(16) 0.10719(6) 0.0316(4) Uani 1 1 d . . . . .
C1 C -0.3427(2) 0.44410(17) 0.16190(6) 0.0218(4) Uani 1 1 d . . . . .
C2 C -0.3770(2) 0.31384(17) 0.14570(6) 0.0213(4) Uani 1 1 d . . . . .
C3 C -0.3215(2) 0.20673(17) 0.16804(6) 0.0208(4) Uani 1 1 d . . . . .
C4 C -0.2002(2) 0.21791(17) 0.20601(6) 0.0218(4) Uani 1 1 d . . . . .
C5 C -0.3718(2) 0.09022(18) 0.15326(6) 0.0234(4) Uani 1 1 d . . . . .
H5A H -0.3370 0.0198 0.1688 0.028 Uiso 1 1 calc R U . . .
C6 C -0.4733(2) 0.07618(18) 0.11569(6) 0.0232(4) Uani 1 1 d . . . . .
C7 C -0.5243(3) 0.18313(19) 0.09326(7) 0.0279(4) Uani 1 1 d . . . . .
H7A H -0.601(3) 0.175(2) 0.0682(8) 0.033 Uiso 1 1 d . U . . .
C8 C -0.4788(3) 0.30018(18) 0.10830(7) 0.0275(4) Uani 1 1 d . . . . .
H8A H -0.5166 0.3705 0.0932 0.033 Uiso 1 1 calc R U . . .
C9 C -0.5268(3) -0.04854(18) 0.09880(6) 0.0248(4) Uani 1 1 d . . . . .
C10 C -0.6174(2) -0.13217(17) 0.12527(6) 0.0199(4) Uani 1 1 d . . . . .
C11 C -0.6670(2) -0.09222(17) 0.17151(6) 0.0207(4) Uani 1 1 d . . . . .
C12 C -0.6734(2) -0.24503(18) 0.10701(6) 0.0243(4) Uani 1 1 d . . . . .
C13 C -0.7624(2) -0.33962(18) 0.13499(6) 0.0240(4) Uani 1 1 d . . . . .
C14 C -0.6395(3) -0.2738(2) 0.06319(7) 0.0416(6) Uani 1 1 d . . . . .
H14A H -0.6780 -0.3483 0.0511 0.050 Uiso 1 1 calc R U . . .
C15 C -0.5487(4) -0.1918(2) 0.03754(8) 0.0536(8) Uani 1 1 d . . . . .
H15A H -0.5253 -0.2115 0.0082 0.064 Uiso 1 1 calc R U . . .
C16 C -0.4926(3) -0.0811(2) 0.05523(7) 0.0418(6) Uani 1 1 d . . . . .
H16A H -0.4306 -0.0270 0.0377 0.050 Uiso 1 1 calc R U . . .
C17 C 0.0517(3) 0.1947(2) 0.11338(8) 0.0352(5) Uani 1 1 d . . . . .
H17A H 0.0748 0.1668 0.1420 0.042 Uiso 1 1 calc R U . . .
C18 C 0.0007(4) 0.3535(2) 0.06585(8) 0.0548(8) Uani 1 1 d . . . . .
H18A H -0.0135 0.4382 0.0605 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0391(3) 0.1073(2) 0.08017(8) 0.0402(5) Uani 1 1 d . . . . .
H19A H 0.0526 0.0231 0.0865 0.048 Uiso 1 1 calc R U . . .
C20 C -0.0127(5) 0.2726(3) 0.03056(9) 0.0669(9) Uani 1 1 d . . . . .
H20A H -0.0345 0.3033 0.0023 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0061(3) 0.1459(2) 0.03713(8) 0.0417(6) Uani 1 1 d . . . . .
C22 C -0.0078(4) 0.0605(2) -0.00068(9) 0.0511(7) Uani 1 1 d . . . . .
H22A H -0.0299 0.0959 -0.0283 0.061 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 O9 2.1221(15) . ?
Mn1 O1 2.1693(14) . ?
Mn1 O8 2.1782(15) 1_665 ?
Mn1 O10 2.2474(14) . ?
Mn1 N1 2.2587(17) . ?
Mn1 O3 2.3105(15) . ?
Mn2 O5 2.1735(14) 2_455 ?
Mn2 O11 2.1744(16) . ?
Mn2 O7 2.1874(15) 2_455 ?
Mn2 O4 2.2008(14) . ?
Mn2 O12 2.2262(14) . ?
Mn2 O2 2.2893(14) 2_445 ?
O1 C1 1.259(2) . ?
O2 C1 1.252(2) . ?
O2 Mn2 2.2892(14) 2_455 ?
O3 C4 1.250(2) . ?
O4 C4 1.265(2) . ?
O5 C11 1.262(2) . ?
O5 Mn2 2.1736(14) 2_445 ?
O6 C11 1.243(2) . ?
O7 C13 1.244(2) . ?
O7 Mn2 2.1874(15) 2_445 ?
O8 C13 1.253(2) . ?
O8 Mn1 2.1782(15) 1_445 ?
O9 H9A 0.842(16) . ?
O9 H9B 0.820(16) . ?
O10 H10A 0.840(16) . ?
O10 H10B 0.871(16) . ?
O11 H11A 0.828(16) . ?
O11 H11B 0.839(16) . ?
O12 H12A 0.843(17) . ?
O12 H12B 0.831(16) . ?
O14 H14B 0.825(18) . ?
O14 H14C 0.842(17) . ?
N1 C17 1.329(3) . ?
N1 C18 1.331(3) . ?
C1 C2 1.505(3) . ?
C2 C8 1.391(3) . ?
C2 C3 1.402(3) . ?
C3 C5 1.385(3) . ?
C3 C4 1.497(3) . ?
C5 C6 1.395(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(3) . ?
C6 C9 1.493(3) . ?
C7 C8 1.383(3) . ?
C7 H7A 0.97(2) . ?
C8 H8A 0.9300 . ?
C9 C16 1.389(3) . ?
C9 C10 1.405(3) . ?
C10 C12 1.402(3) . ?
C10 C11 1.515(3) . ?
C12 C14 1.386(3) . ?
C12 C13 1.502(3) . ?
C14 C15 1.380(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C19 1.376(3) . ?
C17 H17A 0.9300 . ?
C18 C20 1.377(4) . ?
C18 H18A 0.9300 . ?
C19 C21 1.386(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.467(3) . ?
C22 C22 1.305(5) 3 ?
C22 H22A 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 O1 164.71(6) . . ?
O9 Mn1 O8 106.61(6) . 1_665 ?
O1 Mn1 O8 88.68(6) . 1_665 ?
O9 Mn1 O10 85.47(6) . . ?
O1 Mn1 O10 90.35(5) . . ?
O8 Mn1 O10 106.50(6) 1_665 . ?
O9 Mn1 N1 91.77(7) . . ?
O1 Mn1 N1 88.49(6) . . ?
O8 Mn1 N1 88.40(6) 1_665 . ?
O10 Mn1 N1 165.03(6) . . ?
O9 Mn1 O3 82.12(6) . . ?
O1 Mn1 O3 82.59(5) . . ?
O8 Mn1 O3 171.18(6) 1_665 . ?
O10 Mn1 O3 74.96(5) . . ?
N1 Mn1 O3 90.09(6) . . ?
O5 Mn2 O11 83.94(6) 2_455 . ?
O5 Mn2 O7 81.03(6) 2_455 2_455 ?
O11 Mn2 O7 108.43(6) . 2_455 ?
O5 Mn2 O4 123.08(5) 2_455 . ?
O11 Mn2 O4 89.81(6) . . ?
O7 Mn2 O4 151.91(6) 2_455 . ?
O5 Mn2 O12 92.43(6) 2_455 . ?
O11 Mn2 O12 175.26(6) . . ?
O7 Mn2 O12 73.88(6) 2_455 . ?
O4 Mn2 O12 89.62(6) . . ?
O5 Mn2 O2 152.29(6) 2_455 2_445 ?
O11 Mn2 O2 85.80(6) . 2_445 ?
O7 Mn2 O2 77.93(6) 2_455 2_445 ?
O4 Mn2 O2 82.47(5) . 2_445 ?
O12 Mn2 O2 98.79(5) . 2_445 ?
C1 O1 Mn1 118.98(12) . . ?
C1 O2 Mn2 132.22(13) . 2_455 ?
C4 O3 Mn1 142.58(13) . . ?
C4 O4 Mn2 108.21(12) . . ?
C11 O5 Mn2 122.08(12) . 2_445 ?
C13 O7 Mn2 137.56(13) . 2_445 ?
C13 O8 Mn1 112.24(13) . 1_445 ?
Mn1 O9 H9A 128.6(17) . . ?
Mn1 O9 H9B 119.2(18) . . ?
H9A O9 H9B 112(2) . . ?
Mn1 O10 H10A 103.7(17) . . ?
Mn1 O10 H10B 126.8(18) . . ?
H10A O10 H10B 102.5(19) . . ?
Mn2 O11 H11A 111(2) . . ?
Mn2 O11 H11B 104.1(19) . . ?
H11A O11 H11B 112(2) . . ?
Mn2 O12 H12A 121(2) . . ?
Mn2 O12 H12B 106.9(19) . . ?
H12A O12 H12B 110(2) . . ?
H14B O14 H14C 113(3) . . ?
C17 N1 C18 116.47(19) . . ?
C17 N1 Mn1 122.38(15) . . ?
C18 N1 Mn1 120.94(15) . . ?
O2 C1 O1 124.42(17) . . ?
O2 C1 C2 116.68(16) . . ?
O1 C1 C2 118.80(16) . . ?
C8 C2 C3 118.84(17) . . ?
C8 C2 C1 117.63(17) . . ?
C3 C2 C1 123.38(16) . . ?
C5 C3 C2 119.77(17) . . ?
C5 C3 C4 120.09(17) . . ?
C2 C3 C4 120.05(16) . . ?
O3 C4 O4 121.55(18) . . ?
O3 C4 C3 119.22(17) . . ?
O4 C4 C3 119.23(16) . . ?
C3 C5 C6 121.52(18) . . ?
C3 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 118.09(17) . . ?
C7 C6 C9 119.51(17) . . ?
C5 C6 C9 122.40(18) . . ?
C8 C7 C6 121.01(18) . . ?
C8 C7 H7A 119.7(14) . . ?
C6 C7 H7A 119.0(14) . . ?
C7 C8 C2 120.73(18) . . ?
C7 C8 H8A 119.6 . . ?
C2 C8 H8A 119.6 . . ?
C16 C9 C10 118.88(18) . . ?
C16 C9 C6 119.38(17) . . ?
C10 C9 C6 121.69(17) . . ?
C12 C10 C9 119.46(17) . . ?
C12 C10 C11 121.48(16) . . ?
C9 C10 C11 118.78(16) . . ?
O6 C11 O5 125.01(18) . . ?
O6 C11 C10 115.35(17) . . ?
O5 C11 C10 119.62(16) . . ?
C14 C12 C10 120.23(18) . . ?
C14 C12 C13 118.81(17) . . ?
C10 C12 C13 120.88(17) . . ?
O7 C13 O8 122.38(18) . . ?
O7 C13 C12 117.81(17) . . ?
O8 C13 C12 119.80(18) . . ?
C15 C14 C12 119.98(19) . . ?
C15 C14 H14A 120.0 . . ?
C12 C14 H14A 120.0 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C9 121.2(2) . . ?
C15 C16 H16A 119.4 . . ?
C9 C16 H16A 119.4 . . ?
N1 C17 C19 124.2(2) . . ?
N1 C17 H17A 117.9 . . ?
C19 C17 H17A 117.9 . . ?
N1 C18 C20 123.3(2) . . ?
N1 C18 H18A 118.4 . . ?
C20 C18 H18A 118.4 . . ?
C17 C19 C21 119.4(2) . . ?
C17 C19 H19A 120.3 . . ?
C21 C19 H19A 120.3 . . ?
C18 C20 C21 120.1(3) . . ?
C18 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C19 116.6(2) . . ?
C20 C21 C22 119.8(2) . . ?
C19 C21 C22 123.6(2) . . ?
C22 C22 C21 126.2(3) 3 . ?
C22 C22 H22A 116.9 3 . ?
C21 C22 H22A 116.9 . . ?

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 11.9(3) 2_455 . . . ?
Mn2 O2 C1 C2 -164.42(13) 2_455 . . . ?
Mn1 O1 C1 O2 109.91(19) . . . . ?
Mn1 O1 C1 C2 -73.83(19) . . . . ?
O2 C1 C2 C8 90.3(2) . . . . ?
O1 C1 C2 C8 -86.3(2) . . . . ?
O2 C1 C2 C3 -85.2(2) . . . . ?
O1 C1 C2 C3 98.3(2) . . . . ?
C8 C2 C3 C5 -1.5(3) . . . . ?
C1 C2 C3 C5 173.88(18) . . . . ?
C8 C2 C3 C4 174.78(17) . . . . ?
C1 C2 C3 C4 -9.8(3) . . . . ?
Mn1 O3 C4 O4 151.51(16) . . . . ?
Mn1 O3 C4 C3 -27.9(3) . . . . ?
Mn2 O4 C4 O3 2.2(2) . . . . ?
Mn2 O4 C4 C3 -178.42(13) . . . . ?
C5 C3 C4 O3 150.30(19) . . . . ?
C2 C3 C4 O3 -26.0(3) . . . . ?
C5 C3 C4 O4 -29.1(3) . . . . ?
C2 C3 C4 O4 154.58(18) . . . . ?
C2 C3 C5 C6 1.8(3) . . . . ?
C4 C3 C5 C6 -174.51(17) . . . . ?
C3 C5 C6 C7 -0.3(3) . . . . ?
C3 C5 C6 C9 179.06(18) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C9 C6 C7 C8 179.19(19) . . . . ?
C6 C7 C8 C2 1.6(3) . . . . ?
C3 C2 C8 C7 -0.2(3) . . . . ?
C1 C2 C8 C7 -175.84(19) . . . . ?
C7 C6 C9 C16 54.9(3) . . . . ?
C5 C6 C9 C16 -124.5(2) . . . . ?
C7 C6 C9 C10 -122.3(2) . . . . ?
C5 C6 C9 C10 58.3(3) . . . . ?
C16 C9 C10 C12 -1.0(3) . . . . ?
C6 C9 C10 C12 176.20(18) . . . . ?
C16 C9 C10 C11 -175.0(2) . . . . ?
C6 C9 C10 C11 2.2(3) . . . . ?
Mn2 O5 C11 O6 133.27(17) 2_445 . . . ?
Mn2 O5 C11 C10 -48.6(2) 2_445 . . . ?
C12 C10 C11 O6 -91.8(2) . . . . ?
C9 C10 C11 O6 82.1(2) . . . . ?
C12 C10 C11 O5 89.9(2) . . . . ?
C9 C10 C11 O5 -96.2(2) . . . . ?
C9 C10 C12 C14 0.0(3) . . . . ?
C11 C10 C12 C14 173.8(2) . . . . ?
C9 C10 C12 C13 176.63(18) . . . . ?
C11 C10 C12 C13 -9.5(3) . . . . ?
Mn2 O7 C13 O8 155.91(17) 2_445 . . . ?
Mn2 O7 C13 C12 -23.0(3) 2_445 . . . ?
Mn1 O8 C13 O7 -4.6(3) 1_445 . . . ?
Mn1 O8 C13 C12 174.33(14) 1_445 . . . ?
C14 C12 C13 O7 141.1(2) . . . . ?
C10 C12 C13 O7 -35.6(3) . . . . ?
C14 C12 C13 O8 -37.8(3) . . . . ?
C10 C12 C13 O8 145.5(2) . . . . ?
C10 C12 C14 C15 0.8(4) . . . . ?
C13 C12 C14 C15 -175.9(2) . . . . ?
C12 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C9 -0.6(5) . . . . ?
C10 C9 C16 C15 1.3(4) . . . . ?
C6 C9 C16 C15 -175.9(3) . . . . ?
C18 N1 C17 C19 -0.3(4) . . . . ?
Mn1 N1 C17 C19 174.47(19) . . . . ?
C17 N1 C18 C20 -0.2(5) . . . . ?
Mn1 N1 C18 C20 -175.1(3) . . . . ?
N1 C17 C19 C21 0.5(4) . . . . ?
N1 C18 C20 C21 0.6(6) . . . . ?
C18 C20 C21 C19 -0.3(5) . . . . ?
C18 C20 C21 C22 -179.8(3) . . . . ?
C17 C19 C21 C20 -0.2(4) . . . . ?
C17 C19 C21 C22 179.3(3) . . . . ?
C20 C21 C22 C22 179.7(4) . . . 3 ?
C19 C21 C22 C22 0.2(6) . . . 3 ?

_refine_diff_density_max         0.705
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1434502'
_audit_update_record             
;
2015-12-17 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Mn2 N O14'
_chemical_formula_weight         636.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0116(4)
_cell_length_b                   10.7378(5)
_cell_length_c                   30.3601(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.0040(10)
_cell_angle_gamma                90
_cell_volume                     2611.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             1300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.039
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34862
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6315
_reflns_number_gt                5458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Brucker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+8.8614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6315
_refine_ls_number_parameters     396
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.156
_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 0.52942(7) 1.44392(5) 0.16450(2) 0.02078(14) Uani 1 1 d . . . . .
Mn2 Mn 0.49062(7) 1.17659(5) 0.28563(2) 0.02102(14) Uani 1 1 d . . . . .
O1 O 0.2748(3) 1.4941(2) 0.14654(9) 0.0267(6) Uani 1 1 d . . . . .
O2 O 0.0555(3) 1.4789(2) 0.19017(9) 0.0300(6) Uani 1 1 d . . . . .
O3 O 0.3926(3) 1.3000(2) 0.20820(9) 0.0288(6) Uani 1 1 d . . . . .
O4 O 0.3008(3) 1.1236(2) 0.23556(9) 0.0279(6) Uani 1 1 d . . . . .
O5 O -0.2980(4) 0.9620(3) 0.17502(9) 0.0314(6) Uani 1 1 d . . . . .
O6 O -0.0767(4) 0.8667(2) 0.20466(8) 0.0263(6) Uani 1 1 d . . . . .
O7 O -0.2165(4) 0.6379(3) 0.17470(9) 0.0353(7) Uani 1 1 d . . . . .
O8 O -0.3836(4) 0.5877(3) 0.11949(10) 0.0365(7) Uani 1 1 d . . . . .
O9 O 0.5017(3) 1.5386(2) 0.22997(9) 0.0251(5) Uani 1 1 d D . . . .
H9A H 0.413(4) 1.577(4) 0.2352(16) 0.044(15) Uiso 1 1 d D . . . .
H9B H 0.517(8) 1.482(5) 0.2493(19) 0.11(3) Uiso 1 1 d D . . . .
O10 O 0.7459(3) 1.3616(3) 0.19383(10) 0.0309(6) Uani 1 1 d D . . . .
H10B H 0.840(4) 1.399(4) 0.1955(16) 0.039(13) Uiso 1 1 d D . . . .
H10A H 0.742(8) 1.303(4) 0.2124(15) 0.063(18) Uiso 1 1 d D . . . .
O11 O 0.2931(4) 1.2312(3) 0.33030(11) 0.0337(7) Uani 1 1 d D . . . .
H11A H 0.248(6) 1.163(3) 0.3356(16) 0.035(13) Uiso 1 1 d D . . . .
H11B H 0.215(5) 1.267(4) 0.3169(15) 0.038(14) Uiso 1 1 d D . . . .
O12 O 0.6932(3) 1.1363(3) 0.23824(9) 0.0269(6) Uani 1 1 d D . . . .
H12A H 0.691(6) 1.075(3) 0.2203(13) 0.036(13) Uiso 1 1 d D . . . .
H12B H 0.784(4) 1.126(4) 0.2522(13) 0.029(12) Uiso 1 1 d D . . . .
O13 O 0.184(3) 0.541(3) 0.0040(7) 0.127(3) Uani 0.294(8) 1 d . . P . .
O14 O 0.3555(12) 0.7173(11) 0.0690(3) 0.127(3) Uani 0.706(8) 1 d . . P . .
O15 O 0.4364(6) 0.8506(4) 0.21974(16) 0.0684(13) Uani 1 1 d D . . . .
H15B H 0.379(7) 0.911(4) 0.229(2) 0.10(3) Uiso 1 1 d D . . . .
H15C H 0.519(5) 0.881(5) 0.2063(18) 0.061(18) Uiso 1 1 d D . . . .
N1 N 0.5268(4) 1.3048(3) 0.10891(11) 0.0299(7) Uani 1 1 d . . . . .
C1 C 0.1552(4) 1.4350(3) 0.16276(12) 0.0212(7) Uani 1 1 d . . . . .
C2 C 0.1188(4) 1.3044(3) 0.14627(12) 0.0206(7) Uani 1 1 d . . . . .
C3 C 0.1744(4) 1.1979(3) 0.16848(11) 0.0208(7) Uani 1 1 d . . . . .
C4 C 0.2966(4) 1.2082(3) 0.20637(11) 0.0207(7) Uani 1 1 d . . . . .
C5 C 0.1225(4) 1.0804(3) 0.15410(12) 0.0220(7) Uani 1 1 d . . . . .
H5A H 0.1568 1.0099 0.1696 0.026 Uiso 1 1 calc R U . . .
C6 C 0.0193(5) 1.0674(3) 0.11660(11) 0.0210(7) Uani 1 1 d . . . . .
C7 C -0.0306(5) 1.1750(3) 0.09429(12) 0.0271(8) Uani 1 1 d . . . . .
H7A H -0.0965 1.1681 0.0689 0.033 Uiso 1 1 calc R U . . .
C8 C 0.0163(5) 1.2923(3) 0.10926(12) 0.0271(8) Uani 1 1 d . . . . .
H8A H -0.0212 1.3630 0.0944 0.032 Uiso 1 1 calc R U . . .
C9 C -0.0348(4) 0.9432(3) 0.09987(11) 0.0205(7) Uani 1 1 d . . . . .
C10 C -0.1224(4) 0.8588(3) 0.12602(11) 0.0180(6) Uani 1 1 d . . . . .
C11 C -0.1696(4) 0.8971(3) 0.17250(11) 0.0205(7) Uani 1 1 d . . . . .
C12 C -0.1778(5) 0.7455(3) 0.10800(11) 0.0216(7) Uani 1 1 d . . . . .
C13 C -0.2667(4) 0.6511(3) 0.13575(12) 0.0221(7) Uani 1 1 d . . . . .
C14 C -0.1468(6) 0.7175(4) 0.06434(13) 0.0320(9) Uani 1 1 d . . . . .
H14A H -0.1868 0.6435 0.0522 0.038 Uiso 1 1 calc R U . . .
C15 C -0.0564(6) 0.7992(4) 0.03857(13) 0.0370(10) Uani 1 1 d . . . . .
H15A H -0.0322 0.7788 0.0096 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0025(5) 0.9111(4) 0.05623(12) 0.0304(9) Uani 1 1 d . . . . .
H16A H 0.0564 0.9662 0.0387 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5478(6) 1.1833(4) 0.11664(15) 0.0362(9) Uani 1 1 d . . . . .
H17A H 0.5808 1.1586 0.1448 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4831(9) 1.3375(5) 0.06847(17) 0.0624(17) Uani 1 1 d . . . . .
H18A H 0.4694 1.4217 0.0622 0.075 Uiso 1 1 calc R U . . .
C19 C 0.5233(7) 1.0931(4) 0.08525(17) 0.0486(12) Uani 1 1 d . . . . .
H19A H 0.5422 1.0098 0.0921 0.058 Uiso 1 1 calc R U . . .
C20 C 0.4567(12) 1.2526(7) 0.03504(19) 0.090(3) Uani 1 1 d . . . . .
H20A H 0.4295 1.2799 0.0067 0.108 Uiso 1 1 calc R U . . .
C21 C 0.4708(9) 1.1267(6) 0.0437(2) 0.0698(19) Uani 1 1 d . . . . .
C22 C 0.4283(9) 1.0256(8) 0.0090(3) 0.085(2) Uani 1 1 d . . . . .
H22A H 0.3638 0.9601 0.0226 0.102 Uiso 1 1 calc R U . . .
H22B H 0.3602 1.0620 -0.0144 0.102 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 O10 2.128(3) . ?
Mn1 O1 2.170(3) . ?
Mn1 O8 2.184(3) 1_665 ?
Mn1 O9 2.247(3) . ?
Mn1 N1 2.254(3) . ?
Mn1 O3 2.324(3) . ?
Mn2 O6 2.173(3) 2 ?
Mn2 O11 2.182(3) . ?
Mn2 O7 2.196(3) 2 ?
Mn2 O4 2.206(3) . ?
Mn2 O12 2.230(3) . ?
Mn2 O2 2.278(3) 2_545 ?
Mn2 O3 2.799(3) . ?
O1 C1 1.257(4) . ?
O2 C1 1.256(4) . ?
O2 Mn2 2.278(3) 2 ?
O3 C4 1.251(4) . ?
O4 C4 1.269(4) . ?
O5 C11 1.246(4) . ?
O6 C11 1.260(4) . ?
O6 Mn2 2.173(3) 2_545 ?
O7 C13 1.250(5) . ?
O7 Mn2 2.196(3) 2_545 ?
O8 C13 1.253(4) . ?
O8 Mn1 2.184(3) 1_445 ?
O9 H9A 0.842(19) . ?
O9 H9B 0.849(19) . ?
O10 H10B 0.85(2) . ?
O10 H10A 0.84(2) . ?
O11 H11A 0.837(19) . ?
O11 H11B 0.835(19) . ?
O12 H12A 0.855(19) . ?
O12 H12B 0.841(19) . ?
O15 H15B 0.851(19) . ?
O15 H15C 0.851(19) . ?
N1 C18 1.318(6) . ?
N1 C17 1.335(5) . ?
C1 C2 1.516(5) . ?
C2 C8 1.386(5) . ?
C2 C3 1.396(5) . ?
C3 C5 1.396(5) . ?
C3 C4 1.502(5) . ?
C5 C6 1.402(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(5) . ?
C6 C9 1.489(4) . ?
C7 C8 1.389(5) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C16 1.398(5) . ?
C9 C10 1.401(5) . ?
C10 C12 1.403(5) . ?
C10 C11 1.524(5) . ?
C12 C14 1.386(5) . ?
C12 C13 1.505(5) . ?
C14 C15 1.388(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.381(5) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C19 1.371(6) . ?
C17 H17A 0.9300 . ?
C18 C20 1.378(7) . ?
C18 H18A 0.9300 . ?
C19 C21 1.371(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.382(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.548(8) . ?
C22 C22 1.393(13) 3_675 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
O10 Mn1 O1 164.57(11) . . ?
O10 Mn1 O8 106.79(12) . 1_665 ?
O1 Mn1 O8 88.62(11) . 1_665 ?
O10 Mn1 O9 84.86(11) . . ?
O1 Mn1 O9 90.16(10) . . ?
O8 Mn1 O9 105.75(11) 1_665 . ?
O10 Mn1 N1 91.99(12) . . ?
O1 Mn1 N1 88.86(12) . . ?
O8 Mn1 N1 89.94(12) 1_665 . ?
O9 Mn1 N1 164.25(11) . . ?
O10 Mn1 O3 82.77(10) . . ?
O1 Mn1 O3 81.83(10) . . ?
O8 Mn1 O3 170.43(11) 1_665 . ?
O9 Mn1 O3 74.98(10) . . ?
N1 Mn1 O3 89.33(11) . . ?
O6 Mn2 O11 83.98(11) 2 . ?
O6 Mn2 O7 81.20(11) 2 2 ?
O11 Mn2 O7 108.03(12) . 2 ?
O6 Mn2 O4 123.30(10) 2 . ?
O11 Mn2 O4 89.94(12) . . ?
O7 Mn2 O4 151.73(11) 2 . ?
O6 Mn2 O12 92.13(11) 2 . ?
O11 Mn2 O12 175.51(11) . . ?
O7 Mn2 O12 73.45(10) 2 . ?
O4 Mn2 O12 90.34(10) . . ?
O6 Mn2 O2 152.16(10) 2 2_545 ?
O11 Mn2 O2 85.79(10) . 2_545 ?
O7 Mn2 O2 77.50(11) 2 2_545 ?
O4 Mn2 O2 82.43(10) . 2_545 ?
O12 Mn2 O2 98.69(10) . 2_545 ?
O6 Mn2 O3 75.69(9) 2 . ?
O11 Mn2 O3 101.47(11) . . ?
O7 Mn2 O3 140.06(11) 2 . ?
O4 Mn2 O3 50.46(8) . . ?
O12 Mn2 O3 75.33(9) . . ?
O2 Mn2 O3 131.85(9) 2_545 . ?
C1 O1 Mn1 119.7(2) . . ?
C1 O2 Mn2 132.2(2) . 2 ?
C4 O3 Mn1 142.6(2) . . ?
C4 O3 Mn2 80.1(2) . . ?
Mn1 O3 Mn2 131.76(11) . . ?
C4 O4 Mn2 107.8(2) . . ?
C11 O6 Mn2 122.0(2) . 2_545 ?
C13 O7 Mn2 138.2(3) . 2_545 ?
C13 O8 Mn1 112.5(2) . 1_445 ?
Mn1 O9 H9A 119(3) . . ?
Mn1 O9 H9B 106(5) . . ?
H9A O9 H9B 109(3) . . ?
Mn1 O10 H10B 123(3) . . ?
Mn1 O10 H10A 123(4) . . ?
H10B O10 H10A 111(5) . . ?
Mn2 O11 H11A 102(3) . . ?
Mn2 O11 H11B 112(4) . . ?
H11A O11 H11B 101(5) . . ?
Mn2 O12 H12A 124(3) . . ?
Mn2 O12 H12B 109(3) . . ?
H12A O12 H12B 103(4) . . ?
H15B O15 H15C 108(3) . . ?
C18 N1 C17 117.0(4) . . ?
C18 N1 Mn1 121.3(3) . . ?
C17 N1 Mn1 121.1(3) . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C2 116.4(3) . . ?
O1 C1 C2 118.8(3) . . ?
C8 C2 C3 119.6(3) . . ?
C8 C2 C1 117.5(3) . . ?
C3 C2 C1 122.7(3) . . ?
C2 C3 C5 119.9(3) . . ?
C2 C3 C4 120.5(3) . . ?
C5 C3 C4 119.5(3) . . ?
O3 C4 O4 121.6(3) . . ?
O3 C4 C3 119.0(3) . . ?
O4 C4 C3 119.4(3) . . ?
C3 C5 C6 120.8(3) . . ?
C3 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 118.2(3) . . ?
C7 C6 C9 119.8(3) . . ?
C5 C6 C9 122.0(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C2 C8 C7 120.2(3) . . ?
C2 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C16 C9 C10 118.7(3) . . ?
C16 C9 C6 119.1(3) . . ?
C10 C9 C6 122.1(3) . . ?
C9 C10 C12 119.9(3) . . ?
C9 C10 C11 119.0(3) . . ?
C12 C10 C11 120.9(3) . . ?
O5 C11 O6 125.0(3) . . ?
O5 C11 C10 115.2(3) . . ?
O6 C11 C10 119.7(3) . . ?
C14 C12 C10 120.0(3) . . ?
C14 C12 C13 118.9(3) . . ?
C10 C12 C13 121.0(3) . . ?
O7 C13 O8 122.5(3) . . ?
O7 C13 C12 117.3(3) . . ?
O8 C13 C12 120.2(3) . . ?
C12 C14 C15 120.4(3) . . ?
C12 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C9 121.4(3) . . ?
C15 C16 H16A 119.3 . . ?
C9 C16 H16A 119.3 . . ?
N1 C17 C19 123.5(4) . . ?
N1 C17 H17A 118.2 . . ?
C19 C17 H17A 118.2 . . ?
N1 C18 C20 123.0(5) . . ?
N1 C18 H18A 118.5 . . ?
C20 C18 H18A 118.5 . . ?
C21 C19 C17 119.4(5) . . ?
C21 C19 H19A 120.3 . . ?
C17 C19 H19A 120.3 . . ?
C18 C20 C21 119.7(5) . . ?
C18 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C19 C21 C20 117.1(5) . . ?
C19 C21 C22 120.2(6) . . ?
C20 C21 C22 122.7(6) . . ?
C22 C22 C21 111.7(8) 3_675 . ?
C22 C22 H22A 109.3 3_675 . ?
C21 C22 H22A 109.3 . . ?
C22 C22 H22B 109.3 3_675 . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?

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 11.4(6) 2 . . . ?
Mn2 O2 C1 C2 -164.2(2) 2 . . . ?
Mn1 O1 C1 O2 110.6(4) . . . . ?
Mn1 O1 C1 C2 -73.9(4) . . . . ?
O2 C1 C2 C8 89.4(4) . . . . ?
O1 C1 C2 C8 -86.5(4) . . . . ?
O2 C1 C2 C3 -86.0(4) . . . . ?
O1 C1 C2 C3 98.1(4) . . . . ?
C8 C2 C3 C5 -1.9(5) . . . . ?
C1 C2 C3 C5 173.5(3) . . . . ?
C8 C2 C3 C4 175.0(3) . . . . ?
C1 C2 C3 C4 -9.7(5) . . . . ?
Mn1 O3 C4 O4 150.7(3) . . . . ?
Mn2 O3 C4 O4 -1.4(3) . . . . ?
Mn1 O3 C4 C3 -28.9(6) . . . . ?
Mn2 O3 C4 C3 178.9(3) . . . . ?
Mn2 O4 C4 O3 1.9(4) . . . . ?
Mn2 O4 C4 C3 -178.5(3) . . . . ?
C2 C3 C4 O3 -25.7(5) . . . . ?
C5 C3 C4 O3 151.2(4) . . . . ?
C2 C3 C4 O4 154.7(3) . . . . ?
C5 C3 C4 O4 -28.5(5) . . . . ?
C2 C3 C5 C6 2.1(5) . . . . ?
C4 C3 C5 C6 -174.7(3) . . . . ?
C3 C5 C6 C7 -0.3(5) . . . . ?
C3 C5 C6 C9 178.6(3) . . . . ?
C5 C6 C7 C8 -1.7(6) . . . . ?
C9 C6 C7 C8 179.3(4) . . . . ?
C3 C2 C8 C7 -0.2(6) . . . . ?
C1 C2 C8 C7 -175.7(4) . . . . ?
C6 C7 C8 C2 2.0(6) . . . . ?
C7 C6 C9 C16 54.3(5) . . . . ?
C5 C6 C9 C16 -124.5(4) . . . . ?
C7 C6 C9 C10 -123.4(4) . . . . ?
C5 C6 C9 C10 57.7(5) . . . . ?
C16 C9 C10 C12 -1.0(5) . . . . ?
C6 C9 C10 C12 176.8(3) . . . . ?
C16 C9 C10 C11 -175.4(3) . . . . ?
C6 C9 C10 C11 2.4(5) . . . . ?
Mn2 O6 C11 O5 133.0(3) 2_545 . . . ?
Mn2 O6 C11 C10 -50.1(4) 2_545 . . . ?
C9 C10 C11 O5 81.8(4) . . . . ?
C12 C10 C11 O5 -92.5(4) . . . . ?
C9 C10 C11 O6 -95.4(4) . . . . ?
C12 C10 C11 O6 90.2(4) . . . . ?
C9 C10 C12 C14 -0.3(5) . . . . ?
C11 C10 C12 C14 174.0(4) . . . . ?
C9 C10 C12 C13 177.7(3) . . . . ?
C11 C10 C12 C13 -7.9(5) . . . . ?
Mn2 O7 C13 O8 158.3(3) 2_545 . . . ?
Mn2 O7 C13 C12 -20.3(6) 2_545 . . . ?
Mn1 O8 C13 O7 -5.1(5) 1_445 . . . ?
Mn1 O8 C13 C12 173.4(3) 1_445 . . . ?
C14 C12 C13 O7 140.2(4) . . . . ?
C10 C12 C13 O7 -37.9(5) . . . . ?
C14 C12 C13 O8 -38.4(5) . . . . ?
C10 C12 C13 O8 143.5(4) . . . . ?
C10 C12 C14 C15 2.0(6) . . . . ?
C13 C12 C14 C15 -176.1(4) . . . . ?
C12 C14 C15 C16 -2.4(7) . . . . ?
C14 C15 C16 C9 1.0(7) . . . . ?
C10 C9 C16 C15 0.6(6) . . . . ?
C6 C9 C16 C15 -177.2(4) . . . . ?
C18 N1 C17 C19 -1.2(8) . . . . ?
Mn1 N1 C17 C19 170.1(4) . . . . ?
C17 N1 C18 C20 1.0(10) . . . . ?
Mn1 N1 C18 C20 -170.4(6) . . . . ?
N1 C17 C19 C21 -1.6(9) . . . . ?
N1 C18 C20 C21 2.1(13) . . . . ?
C17 C19 C21 C20 4.5(10) . . . . ?
C17 C19 C21 C22 -174.9(6) . . . . ?
C18 C20 C21 C19 -4.7(12) . . . . ?
C18 C20 C21 C22 174.6(7) . . . . ?
C19 C21 C22 C22 -77.6(13) . . . 3_675 ?
C20 C21 C22 C22 103.1(12) . . . 3_675 ?

_refine_diff_density_max         1.095
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.098

_shelxl_version_number           2014-3



