# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1432831'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-01-20 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            'C11 H13 N5 O5 Zn'
_chemical_formula_weight         360.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.0970(9)
_cell_length_b                   12.8101(11)
_cell_length_c                   10.9229(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.581(2)
_cell_angle_gamma                90
_cell_volume                     1378.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    877
_cell_measurement_theta_min      4.1480
_cell_measurement_theta_max      70.5510

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.806
_shelx_estimated_absorpt_T_min   0.604
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3031
_exptl_absorpt_correction_T_max  0.7801
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4221
_diffrn_reflns_av_unetI/netI     0.1468
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.664
_diffrn_reflns_theta_max         66.183
_diffrn_reflns_theta_full        66.183
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2368
_reflns_number_gt                1278
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2368
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2196
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.73124(11) 0.35523(9) 0.27988(10) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.2584(7) 0.7411(5) 0.5739(6) 0.0376(17) Uani 1 1 d . . . . .
N2 N 0.2655(8) 0.8462(6) 0.5881(7) 0.047(2) Uani 1 1 d . . . . .
N3 N 0.2806(8) 0.8859(6) 0.4818(8) 0.050(2) Uani 1 1 d . . . . .
N4 N 0.2818(7) 0.8107(6) 0.3977(6) 0.0372(17) Uani 1 1 d . . . . .
O1 O -0.1105(5) 0.4528(5) 0.3059(6) 0.0482(16) Uani 1 1 d . . . . .
O2 O 0.0002(6) 0.3063(5) 0.2859(6) 0.0546(18) Uani 1 1 d . . . . .
O3 O 0.4752(6) 0.3254(5) 0.2491(6) 0.0580(19) Uani 1 1 d . . . . .
O4 O 0.5995(6) 0.4667(4) 0.3054(6) 0.0456(15) Uani 1 1 d . . . . .
C10 C 0.9084(12) 0.6124(10) 0.0371(11) 0.078(4) Uani 1 1 d . . . . .
O6 O 0.7322(10) 0.6691(7) 0.3671(9) 0.114(3) Uani 1 1 d . . . . .
C1 C -0.0034(9) 0.4010(8) 0.3037(8) 0.045(2) Uani 1 1 d . . . . .
C2 C 0.4867(9) 0.4166(7) 0.2861(8) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.2678(8) 0.7229(7) 0.4578(8) 0.038(2) Uani 1 1 d . . . . .
C4 C 0.1286(8) 0.4630(7) 0.3293(8) 0.040(2) Uani 1 1 d . . . . .
C5 C 0.2422(8) 0.4174(7) 0.2982(7) 0.038(2) Uani 1 1 d . . . . .
H5 H 0.2356 0.3511 0.2629 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3656(8) 0.4706(7) 0.3197(7) 0.039(2) Uani 1 1 d . . . . .
C7 C 0.3752(8) 0.5715(7) 0.3696(8) 0.041(2) Uani 1 1 d . . . . .
H7 H 0.4568 0.6078 0.3820 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2605(8) 0.6177(7) 0.4009(8) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.1377(8) 0.5631(7) 0.3800(7) 0.037(2) Uani 1 1 d . . . . .
H9 H 0.0617 0.5938 0.4000 0.045 Uiso 1 1 calc R U . . .
N5 N 0.8224(11) 0.6424(9) 0.1234(11) 0.099(4) Uani 1 1 d . . . . .
C11 C 0.6709(13) 0.6494(9) 0.0649(13) 0.087(4) 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
Zn1 N4 1.999(6) 2_645 ?
Zn1 O1 1.999(6) 1_655 ?
Zn1 N1 2.003(7) 3_666 ?
Zn1 O4 2.012(6) . ?
N1 C3 1.313(10) . ?
N1 N2 1.355(9) . ?
N1 Zn1 2.003(7) 3_666 ?
N2 N3 1.306(10) . ?
N3 N4 1.333(10) . ?
N4 C3 1.326(10) . ?
N4 Zn1 1.999(6) 2_655 ?
O1 C1 1.273(10) . ?
O1 Zn1 2.000(6) 1_455 ?
O2 C1 1.231(11) . ?
O3 C2 1.234(10) . ?
O4 C2 1.284(10) . ?
C10 N5 1.465(15) . ?
C1 C4 1.524(11) . ?
C2 C6 1.518(11) . ?
C3 C8 1.479(11) . ?
C4 C9 1.391(11) . ?
C4 C5 1.393(11) . ?
C5 C6 1.394(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(11) . ?
C7 C8 1.408(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(11) . ?
C9 H9 0.9300 . ?
N5 C11 1.527(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 O1 101.4(3) 2_645 1_655 ?
N4 Zn1 N1 125.4(3) 2_645 3_666 ?
O1 Zn1 N1 111.7(3) 1_655 3_666 ?
N4 Zn1 O4 115.5(3) 2_645 . ?
O1 Zn1 O4 94.0(2) 1_655 . ?
N1 Zn1 O4 104.4(3) 3_666 . ?
C3 N1 N2 106.0(7) . . ?
C3 N1 Zn1 131.1(6) . 3_666 ?
N2 N1 Zn1 121.9(5) . 3_666 ?
N3 N2 N1 107.3(7) . . ?
N2 N3 N4 110.6(7) . . ?
C3 N4 N3 104.7(7) . . ?
C3 N4 Zn1 137.0(6) . 2_655 ?
N3 N4 Zn1 117.0(6) . 2_655 ?
C1 O1 Zn1 109.2(6) . 1_455 ?
C2 O4 Zn1 102.2(5) . . ?
O2 C1 O1 124.8(9) . . ?
O2 C1 C4 119.2(9) . . ?
O1 C1 C4 116.0(8) . . ?
O3 C2 O4 123.0(8) . . ?
O3 C2 C6 119.2(8) . . ?
O4 C2 C6 117.7(8) . . ?
N1 C3 N4 111.4(8) . . ?
N1 C3 C8 124.2(8) . . ?
N4 C3 C8 124.4(7) . . ?
C9 C4 C5 119.8(8) . . ?
C9 C4 C1 122.2(8) . . ?
C5 C4 C1 118.0(8) . . ?
C4 C5 C6 120.5(8) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.1(8) . . ?
C5 C6 C2 118.3(8) . . ?
C7 C6 C2 121.6(8) . . ?
C6 C7 C8 119.5(8) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 119.8(8) . . ?
C9 C8 C3 119.1(7) . . ?
C7 C8 C3 121.1(8) . . ?
C4 C9 C8 120.3(8) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 N5 C11 115.2(10) . . ?

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
C3 N1 N2 N3 -0.9(10) . . . . ?
Zn1 N1 N2 N3 168.8(5) 3_666 . . . ?
N1 N2 N3 N4 0.8(10) . . . . ?
N2 N3 N4 C3 -0.5(10) . . . . ?
N2 N3 N4 Zn1 168.8(5) . . . 2_655 ?
Zn1 O1 C1 O2 1.2(12) 1_455 . . . ?
Zn1 O1 C1 C4 -176.8(6) 1_455 . . . ?
Zn1 O4 C2 O3 -6.2(10) . . . . ?
Zn1 O4 C2 C6 169.3(6) . . . . ?
N2 N1 C3 N4 0.6(10) . . . . ?
Zn1 N1 C3 N4 -167.7(6) 3_666 . . . ?
N2 N1 C3 C8 -178.1(7) . . . . ?
Zn1 N1 C3 C8 13.6(12) 3_666 . . . ?
N3 N4 C3 N1 -0.1(9) . . . . ?
Zn1 N4 C3 N1 -166.0(6) 2_655 . . . ?
N3 N4 C3 C8 178.6(7) . . . . ?
Zn1 N4 C3 C8 12.6(14) 2_655 . . . ?
O2 C1 C4 C9 -163.9(9) . . . . ?
O1 C1 C4 C9 14.2(12) . . . . ?
O2 C1 C4 C5 17.4(13) . . . . ?
O1 C1 C4 C5 -164.5(8) . . . . ?
C9 C4 C5 C6 1.2(13) . . . . ?
C1 C4 C5 C6 -180.0(7) . . . . ?
C4 C5 C6 C7 -1.8(12) . . . . ?
C4 C5 C6 C2 179.0(7) . . . . ?
O3 C2 C6 C5 -4.9(12) . . . . ?
O4 C2 C6 C5 179.5(7) . . . . ?
O3 C2 C6 C7 175.9(8) . . . . ?
O4 C2 C6 C7 0.3(12) . . . . ?
C5 C6 C7 C8 1.6(13) . . . . ?
C2 C6 C7 C8 -179.2(7) . . . . ?
C6 C7 C8 C9 -1.0(12) . . . . ?
C6 C7 C8 C3 177.9(8) . . . . ?
N1 C3 C8 C9 67.7(11) . . . . ?
N4 C3 C8 C9 -110.8(10) . . . . ?
N1 C3 C8 C7 -111.2(10) . . . . ?
N4 C3 C8 C7 70.4(11) . . . . ?
C5 C4 C9 C8 -0.6(13) . . . . ?
C1 C4 C9 C8 -179.3(8) . . . . ?
C7 C8 C9 C4 0.5(12) . . . . ?
C3 C8 C9 C4 -178.4(8) . . . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -1.068
_refine_diff_density_rms         0.135

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1432832'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-01-20 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            'C12 H16 Cd2 N5 O8.50'
_chemical_formula_weight         591.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.626 0.249 0.265 113 44 ' '
2 0.374 0.749 0.735 113 44 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_cell_length_a                   10.4622(9)
_cell_length_b                   7.1870(6)
_cell_length_c                   13.4544(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.694(2)
_cell_angle_gamma                90
_cell_volume                     933.34(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    921
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      70.9460

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    18.758
_shelx_estimated_absorpt_T_min   0.099
_shelx_estimated_absorpt_T_max   0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0985
_exptl_absorpt_correction_T_max  0.1784
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3248
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.561
_diffrn_reflns_theta_max         68.212
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1858
_reflns_number_gt                1266
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1858
_refine_ls_number_parameters     134
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1811
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.85630(9) 0.2500 0.72512(7) 0.0445(5) Uani 1 2 d S T P . .
Cd2 Cd 1.0000 0.0000 1.0000 0.0516(5) Uani 1 2 d S U P . .
N1 N 0.1355(9) 0.0964(17) 0.2606(6) 0.046(2) Uani 1 1 d . U . . .
N2 N 0.0964(9) 0.1572(17) 0.1618(6) 0.060(4) Uani 1 1 d . . . . .
O1 O 0.6350(10) 0.2500 0.6226(9) 0.060(4) Uani 1 2 d S T P . .
O2 O 0.6056(11) 0.2500 0.7767(9) 0.077(5) Uani 1 2 d S T P . .
O3 O 0.1143(14) 0.2500 0.7627(9) 0.084(6) Uani 1 2 d S T P . .
O4 O -0.0564(12) 0.2500 0.6015(9) 0.073(5) Uani 1 2 d S T P . .
O5 O 0.9025(12) 0.2500 0.9024(8) 0.054(3) Uani 1 2 d S T P . .
O6 O 0.8025(10) -0.0342(19) 1.0423(8) 0.088(4) Uani 1 1 d . . . . .
O8 O 0.562(4) 0.342(6) 0.948(3) 0.078(14) Uani 0.25 1 d . . P A -1
C1 C 0.5640(12) 0.2500 0.6791(11) 0.035(4) Uani 1 2 d S T P . .
C2 C 0.4078(13) 0.2500 0.6145(11) 0.037(4) Uani 1 2 d S T P . .
C3 C 0.3594(13) 0.2500 0.5052(10) 0.033(4) Uani 1 2 d S T P . .
H3 H 0.4215 0.2500 0.4710 0.039 Uiso 1 2 calc R U P . .
C4 C 0.2143(14) 0.2500 0.4427(11) 0.036(4) Uani 1 2 d S T P . .
C5 C 0.1264(15) 0.2500 0.4930(11) 0.065(7) Uani 1 2 d S T P . .
H5 H 0.0313 0.2500 0.4535 0.079 Uiso 1 2 calc R U P . .
C6 C 0.1796(15) 0.2500 0.6080(11) 0.035(3) Uani 1 2 d S TU P . .
C7 C 0.3142(15) 0.2500 0.6678(10) 0.041(4) Uani 1 2 d S T P . .
H7 H 0.3464 0.2500 0.7426 0.049 Uiso 1 2 calc R U P . .
C8 C 0.0711(17) 0.2500 0.6590(12) 0.061(6) Uani 1 2 d S T P . .
C9 C 0.1639(14) 0.2500 0.3226(11) 0.044(4) Uani 1 2 d S T 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
Cd1 O4 2.185(11) 1_655 ?
Cd1 O1 2.191(9) . ?
Cd1 O5 2.243(10) . ?
Cd1 N1 2.496(13) 2_656 ?
Cd1 N1 2.496(13) 3_656 ?
Cd1 O3 2.547(13) 1_655 ?
Cd1 C8 2.717(16) 1_655 ?
Cd2 O5 2.227(6) . ?
Cd2 O5 2.227(6) 3_757 ?
Cd2 N2 2.311(9) 3_656 ?
Cd2 N2 2.311(9) 1_656 ?
Cd2 O6 2.358(10) 3_757 ?
Cd2 O6 2.358(10) . ?
N1 N2 1.306(11) . ?
N1 C9 1.346(13) . ?
N1 Cd1 2.496(12) 3_656 ?
N2 N2 1.33(3) 4_565 ?
N2 Cd2 2.311(9) 1_454 ?
O1 C1 1.252(18) . ?
O2 C1 1.212(18) . ?
O3 C8 1.289(18) . ?
O3 Cd1 2.547(13) 1_455 ?
O4 C8 1.26(2) . ?
O4 Cd1 2.185(11) 1_455 ?
O5 Cd2 2.227(6) 2_757 ?
C1 C2 1.527(16) . ?
C2 C3 1.358(17) . ?
C2 C7 1.42(2) . ?
C3 C4 1.424(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.34(2) . ?
C4 C9 1.493(18) . ?
C5 C6 1.428(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.32(2) . ?
C6 C8 1.537(19) . ?
C7 H7 0.9300 . ?
C8 Cd1 2.717(16) 1_455 ?
C9 N1 1.346(13) 4_565 ?

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
O4 Cd1 O1 99.9(4) 1_655 . ?
O4 Cd1 O5 145.8(4) 1_655 . ?
O1 Cd1 O5 114.3(4) . . ?
O4 Cd1 N1 92.66(19) 1_655 2_656 ?
O1 Cd1 N1 92.6(2) . 2_656 ?
O5 Cd1 N1 86.06(17) . 2_656 ?
O4 Cd1 N1 92.66(18) 1_655 3_656 ?
O1 Cd1 N1 92.6(2) . 3_656 ?
O5 Cd1 N1 86.06(17) . 3_656 ?
N1 Cd1 N1 171.8(3) 2_656 3_656 ?
O4 Cd1 O3 55.2(4) 1_655 1_655 ?
O1 Cd1 O3 155.0(4) . 1_655 ?
O5 Cd1 O3 90.7(4) . 1_655 ?
N1 Cd1 O3 89.0(2) 2_656 1_655 ?
N1 Cd1 O3 89.0(2) 3_656 1_655 ?
O4 Cd1 C8 27.0(4) 1_655 1_655 ?
O1 Cd1 C8 126.9(4) . 1_655 ?
O5 Cd1 C8 118.8(4) . 1_655 ?
N1 Cd1 C8 91.0(2) 2_656 1_655 ?
N1 Cd1 C8 91.0(2) 3_656 1_655 ?
O3 Cd1 C8 28.1(4) 1_655 1_655 ?
O5 Cd2 O5 180.0 . 3_757 ?
O5 Cd2 N2 84.5(4) . 3_656 ?
O5 Cd2 N2 95.5(4) 3_757 3_656 ?
O5 Cd2 N2 95.5(4) . 1_656 ?
O5 Cd2 N2 84.5(4) 3_757 1_656 ?
N2 Cd2 N2 180.0 3_656 1_656 ?
O5 Cd2 O6 91.0(4) . 3_757 ?
O5 Cd2 O6 89.0(4) 3_757 3_757 ?
N2 Cd2 O6 85.9(4) 3_656 3_757 ?
N2 Cd2 O6 94.1(4) 1_656 3_757 ?
O5 Cd2 O6 89.0(4) . . ?
O5 Cd2 O6 91.0(4) 3_757 . ?
N2 Cd2 O6 94.1(4) 3_656 . ?
N2 Cd2 O6 85.9(4) 1_656 . ?
O6 Cd2 O6 180.0 3_757 . ?
N2 N1 C9 105.3(11) . . ?
N2 N1 Cd1 113.6(8) . 3_656 ?
C9 N1 Cd1 141.0(7) . 3_656 ?
N1 N2 N2 109.5(7) . 4_565 ?
N1 N2 Cd2 130.3(9) . 1_454 ?
N2 N2 Cd2 119.3(3) 4_565 1_454 ?
C1 O1 Cd1 110.3(8) . . ?
C8 O3 Cd1 83.3(10) . 1_455 ?
C8 O4 Cd1 100.8(10) . 1_455 ?
Cd2 O5 Cd2 107.6(4) 2_757 . ?
Cd2 O5 Cd1 119.3(3) 2_757 . ?
Cd2 O5 Cd1 119.3(3) . . ?
O2 C1 O1 127.5(12) . . ?
O2 C1 C2 118.4(13) . . ?
O1 C1 C2 114.2(12) . . ?
C3 C2 C7 120.4(12) . . ?
C3 C2 C1 119.1(14) . . ?
C7 C2 C1 120.5(12) . . ?
C2 C3 C4 120.4(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.1(12) . . ?
C5 C4 C9 121.6(12) . . ?
C3 C4 C9 119.3(12) . . ?
C4 C5 C6 119.5(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 122.4(12) . . ?
C7 C6 C8 121.6(12) . . ?
C5 C6 C8 116.0(13) . . ?
C6 C7 C2 118.2(12) . . ?
C6 C7 H7 120.9 . . ?
C2 C7 H7 120.9 . . ?
O4 C8 O3 120.8(15) . . ?
O4 C8 C6 121.0(13) . . ?
O3 C8 C6 118.2(14) . . ?
O4 C8 Cd1 52.2(8) . 1_455 ?
O3 C8 Cd1 68.6(9) . 1_455 ?
C6 C8 Cd1 173.2(11) . 1_455 ?
N1 C9 N1 110.2(13) 4_565 . ?
N1 C9 C4 124.9(6) 4_565 . ?
N1 C9 C4 124.9(6) . . ?

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
C9 N1 N2 N2 -1.8(10) . . . 4_565 ?
Cd1 N1 N2 N2 -179.3(3) 3_656 . . 4_565 ?
C9 N1 N2 Cd2 -170.7(8) . . . 1_454 ?
Cd1 N1 N2 Cd2 11.8(11) 3_656 . . 1_454 ?
Cd1 O1 C1 O2 0.000(6) . . . . ?
Cd1 O1 C1 C2 180.000 . . . . ?
O2 C1 C2 C3 180.000 . . . . ?
O1 C1 C2 C3 0.000(5) . . . . ?
O2 C1 C2 C7 0.000(6) . . . . ?
O1 C1 C2 C7 180.000 . . . . ?
C7 C2 C3 C4 0.000(5) . . . . ?
C1 C2 C3 C4 180.000 . . . . ?
C2 C3 C4 C5 0.000(5) . . . . ?
C2 C3 C4 C9 180.000(4) . . . . ?
C3 C4 C5 C6 0.000(5) . . . . ?
C9 C4 C5 C6 180.000 . . . . ?
C4 C5 C6 C7 0.000(6) . . . . ?
C4 C5 C6 C8 180.000 . . . . ?
C5 C6 C7 C2 0.000(6) . . . . ?
C8 C6 C7 C2 180.000 . . . . ?
C3 C2 C7 C6 0.000(7) . . . . ?
C1 C2 C7 C6 180.000 . . . . ?
Cd1 O4 C8 O3 0.000(6) 1_455 . . . ?
Cd1 O4 C8 C6 180.000 1_455 . . . ?
Cd1 O3 C8 O4 0.000(5) 1_455 . . . ?
Cd1 O3 C8 C6 180.000 1_455 . . . ?
C7 C6 C8 O4 180.000 . . . . ?
C5 C6 C8 O4 0.000(7) . . . . ?
C7 C6 C8 O3 0.000(7) . . . . ?
C5 C6 C8 O3 180.000 . . . . ?
N2 N1 C9 N1 3.0(16) . . . 4_565 ?
Cd1 N1 C9 N1 179.4(3) 3_656 . . 4_565 ?
N2 N1 C9 C4 -179.3(12) . . . . ?
Cd1 N1 C9 C4 -3(2) 3_656 . . . ?
C5 C4 C9 N1 88.7(13) . . . 4_565 ?
C3 C4 C9 N1 -91.3(13) . . . 4_565 ?
C5 C4 C9 N1 -88.7(13) . . . . ?
C3 C4 C9 N1 91.3(13) . . . . ?

_refine_diff_density_max         1.911
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.203

####################################################################### 
# 
# 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 1432833'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-01-20 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            'C9 H7 Mn N4 Na O6'
_chemical_formula_weight         345.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   19.571(2)
_cell_length_b                   11.0278(9)
_cell_length_c                   13.2983(12)
_cell_angle_alpha                90
_cell_angle_beta                 124.0840(10)
_cell_angle_gamma                90
_cell_volume                     2377.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4012
_cell_measurement_theta_min      4.85
_cell_measurement_theta_max      66.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.783
_shelx_estimated_absorpt_T_min   0.304
_shelx_estimated_absorpt_T_max   0.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3036
_exptl_absorpt_correction_T_max  0.4125
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   sadabs
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4012
_diffrn_reflns_av_unetI/netI     0.1296
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.850
_diffrn_reflns_theta_max         66.189
_diffrn_reflns_theta_full        66.189
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2082
_reflns_number_gt                1191
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2082
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.33914(7) 0.38966(11) 0.21572(11) 0.0274(3) Uani 1 1 d . . . . .
Na1 Na 0.2762(2) 0.6959(3) 0.2492(3) 0.0452(9) Uani 1 1 d . . . . .
O1 O 0.7442(3) 0.9701(4) 0.6131(4) 0.0301(13) Uani 1 1 d . . . . .
O2 O 0.6996(3) 1.1589(4) 0.5802(4) 0.0280(13) Uani 1 1 d . . . . .
O3 O 0.4004(3) 1.2324(5) 0.3004(5) 0.0438(16) Uani 1 1 d . . . . .
O4 O 0.3105(3) 1.0837(5) 0.2124(5) 0.0401(15) Uani 1 1 d . . . . .
O5 O 0.2943(3) 0.3862(5) 0.3473(4) 0.0375(14) Uani 1 1 d . . . . .
H5A H 0.2620 0.4441 0.3360 0.045 Uiso 1 1 d R U . . .
H5B H 0.3331 0.3793 0.4219 0.045 Uiso 1 1 d R U . . .
O6 O 0.3586(3) 0.3636(5) 0.0725(5) 0.0451(16) Uani 1 1 d . . . . .
H6A H 0.3507 0.2909 0.0472 0.054 Uiso 1 1 d R U . . .
H6B H 0.4061 0.3875 0.0930 0.054 Uiso 1 1 d R U . . .
N1 N 0.4174(4) 0.6470(5) 0.3133(5) 0.0304(16) Uani 1 1 d . . . . .
N2 N 0.4326(4) 0.5273(5) 0.3218(5) 0.0267(15) Uani 1 1 d . . . . .
N3 N 0.5127(4) 0.5084(5) 0.3875(5) 0.0287(16) Uani 1 1 d . . . . .
N4 N 0.5517(3) 0.6157(5) 0.4209(5) 0.0263(14) Uani 1 1 d . . . . .
C1 C 0.4918(4) 0.6993(6) 0.3727(6) 0.0210(16) Uani 1 1 d . . . . .
C2 C 0.5065(4) 0.8304(7) 0.3829(6) 0.0204(16) Uani 1 1 d . . . . .
C3 C 0.5863(4) 0.8753(6) 0.4575(6) 0.0223(17) Uani 1 1 d . . . . .
H3 H 0.6305 0.8219 0.4982 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6003(4) 1.0005(7) 0.4717(6) 0.0203(16) Uani 1 1 d . . . . .
C5 C 0.5332(4) 1.0793(6) 0.4107(6) 0.0216(17) Uani 1 1 d . . . . .
H5 H 0.5420 1.1626 0.4212 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4535(5) 1.0353(7) 0.3346(6) 0.0244(17) Uani 1 1 d . . . . .
C7 C 0.4411(4) 0.9120(6) 0.3219(6) 0.0235(17) Uani 1 1 d . . . . .
H7 H 0.3877 0.8823 0.2712 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6857(5) 1.0464(6) 0.5608(6) 0.0244(18) Uani 1 1 d . . . . .
C9 C 0.3823(4) 1.1218(7) 0.2751(7) 0.0265(18) 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 O3 2.049(5) 1_545 ?
Mn1 O6 2.161(5) . ?
Mn1 N2 2.179(6) . ?
Mn1 O1 2.206(5) 8_465 ?
Mn1 O2 2.340(5) 8_465 ?
Mn1 O5 2.357(5) . ?
Mn1 C8 2.613(7) 8_465 ?
Mn1 Na1 3.325(4) 4_545 ?
Mn1 Na1 3.706(3) . ?
Na1 O4 2.374(7) 4_545 ?
Na1 O1 2.397(6) 8_465 ?
Na1 O5 2.444(6) 4 ?
Na1 N1 2.452(7) . ?
Na1 O2 2.595(6) 5_676 ?
Na1 C9 3.044(8) 4_545 ?
Na1 Mn1 3.325(4) 4 ?
O1 C8 1.269(8) . ?
O1 Mn1 2.206(5) 8_566 ?
O1 Na1 2.397(6) 8_566 ?
O2 C8 1.265(8) . ?
O2 Mn1 2.340(5) 8_566 ?
O2 Na1 2.595(6) 5_676 ?
O3 C9 1.263(9) . ?
O3 Mn1 2.049(5) 1_565 ?
O4 C9 1.238(9) . ?
O4 Na1 2.375(7) 4 ?
O5 Na1 2.444(6) 4_545 ?
O5 H5A 0.8499 . ?
O5 H5B 0.8500 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8499 . ?
N1 C1 1.338(9) . ?
N1 N2 1.344(8) . ?
N2 N3 1.315(8) . ?
N3 N4 1.341(8) . ?
N4 C1 1.339(9) . ?
C1 C2 1.466(9) . ?
C2 C3 1.389(9) . ?
C2 C7 1.394(9) . ?
C3 C4 1.400(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(9) . ?
C4 C8 1.495(9) . ?
C5 C6 1.387(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(9) . ?
C6 C9 1.496(9) . ?
C7 H7 0.9300 . ?
C8 Mn1 2.613(7) 8_566 ?
C9 Na1 3.044(8) 4 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Mn1 O6 92.0(2) 1_545 . ?
O3 Mn1 N2 102.3(2) 1_545 . ?
O6 Mn1 N2 99.5(2) . . ?
O3 Mn1 O1 164.6(2) 1_545 8_465 ?
O6 Mn1 O1 92.9(2) . 8_465 ?
N2 Mn1 O1 91.3(2) . 8_465 ?
O3 Mn1 O2 107.5(2) 1_545 8_465 ?
O6 Mn1 O2 89.81(19) . 8_465 ?
N2 Mn1 O2 148.4(2) . 8_465 ?
O1 Mn1 O2 57.90(17) 8_465 8_465 ?
O3 Mn1 O5 85.7(2) 1_545 . ?
O6 Mn1 O5 167.2(2) . . ?
N2 Mn1 O5 93.3(2) . . ?
O1 Mn1 O5 86.30(19) 8_465 . ?
O2 Mn1 O5 78.99(18) 8_465 . ?
O3 Mn1 C8 136.2(2) 1_545 8_465 ?
O6 Mn1 C8 91.9(2) . 8_465 ?
N2 Mn1 C8 120.0(2) . 8_465 ?
O1 Mn1 C8 28.98(19) 8_465 8_465 ?
O2 Mn1 C8 28.92(18) 8_465 8_465 ?
O5 Mn1 C8 81.3(2) . 8_465 ?
O3 Mn1 Na1 67.24(18) 1_545 4_545 ?
O6 Mn1 Na1 120.46(16) . 4_545 ?
N2 Mn1 Na1 138.29(19) . 4_545 ?
O1 Mn1 Na1 97.73(15) 8_465 4_545 ?
O2 Mn1 Na1 50.98(14) 8_465 4_545 ?
O5 Mn1 Na1 47.26(14) . 4_545 ?
C8 Mn1 Na1 73.35(18) 8_465 4_545 ?
O3 Mn1 Na1 146.78(17) 1_545 . ?
O6 Mn1 Na1 117.50(16) . . ?
N2 Mn1 Na1 60.18(17) . . ?
O1 Mn1 Na1 38.18(14) 8_465 . ?
O2 Mn1 Na1 88.72(13) 8_465 . ?
O5 Mn1 Na1 68.78(14) . . ?
C8 Mn1 Na1 62.37(17) 8_465 . ?
Na1 Mn1 Na1 105.74(4) 4_545 . ?
O4 Na1 O1 81.3(2) 4_545 8_465 ?
O4 Na1 O5 107.4(2) 4_545 4 ?
O1 Na1 O5 115.3(2) 8_465 4 ?
O4 Na1 N1 127.8(2) 4_545 . ?
O1 Na1 N1 82.0(2) 8_465 . ?
O5 Na1 N1 124.4(2) 4 . ?
O4 Na1 O2 86.3(2) 4_545 5_676 ?
O1 Na1 O2 166.9(2) 8_465 5_676 ?
O5 Na1 O2 72.64(18) 4 5_676 ?
N1 Na1 O2 102.3(2) . 5_676 ?
O4 Na1 C9 22.33(19) 4_545 4_545 ?
O1 Na1 C9 84.0(2) 8_465 4_545 ?
O5 Na1 C9 86.2(2) 4 4_545 ?
N1 Na1 C9 149.4(2) . 4_545 ?
O2 Na1 C9 86.3(2) 5_676 4_545 ?
O4 Na1 Mn1 71.46(16) 4_545 4 ?
O1 Na1 Mn1 133.31(17) 8_465 4 ?
O5 Na1 Mn1 45.08(14) 4 4 ?
N1 Na1 Mn1 144.44(19) . 4 ?
O2 Na1 Mn1 44.47(12) 5_676 4 ?
C9 Na1 Mn1 57.07(16) 4_545 4 ?
O4 Na1 Mn1 82.93(16) 4_545 . ?
O1 Na1 Mn1 34.67(12) 8_465 . ?
O5 Na1 Mn1 147.93(17) 4 . ?
N1 Na1 Mn1 57.03(16) . . ?
O2 Na1 Mn1 139.24(16) 5_676 . ?
C9 Na1 Mn1 97.49(17) 4_545 . ?
Mn1 Na1 Mn1 154.16(11) 4 . ?
C8 O1 Mn1 93.6(4) . 8_566 ?
C8 O1 Na1 134.0(5) . 8_566 ?
Mn1 O1 Na1 107.2(2) 8_566 8_566 ?
C8 O2 Mn1 87.6(4) . 8_566 ?
C8 O2 Na1 134.2(5) . 5_676 ?
Mn1 O2 Na1 84.55(17) 8_566 5_676 ?
C9 O3 Mn1 132.9(5) . 1_565 ?
C9 O4 Na1 110.9(5) . 4 ?
Mn1 O5 Na1 87.66(19) . 4_545 ?
Mn1 O5 H5A 113.9 . . ?
Na1 O5 H5A 114.0 4_545 . ?
Mn1 O5 H5B 114.1 . . ?
Na1 O5 H5B 114.0 4_545 . ?
H5A O5 H5B 111.4 . . ?
Mn1 O6 H6A 113.0 . . ?
Mn1 O6 H6B 112.1 . . ?
H6A O6 H6B 110.1 . . ?
C1 N1 N2 104.8(6) . . ?
C1 N1 Na1 138.9(5) . . ?
N2 N1 Na1 113.5(5) . . ?
N3 N2 N1 109.7(6) . . ?
N3 N2 Mn1 125.1(5) . . ?
N1 N2 Mn1 124.3(5) . . ?
N2 N3 N4 109.0(6) . . ?
C1 N4 N3 105.4(6) . . ?
N1 C1 N4 111.0(6) . . ?
N1 C1 C2 124.9(7) . . ?
N4 C1 C2 124.2(7) . . ?
C3 C2 C7 118.9(7) . . ?
C3 C2 C1 120.0(7) . . ?
C7 C2 C1 121.0(7) . . ?
C2 C3 C4 120.3(7) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.2(7) . . ?
C5 C4 C8 121.3(7) . . ?
C3 C4 C8 119.2(7) . . ?
C6 C5 C4 120.9(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 119.0(7) . . ?
C7 C6 C9 121.2(7) . . ?
C5 C6 C9 119.7(7) . . ?
C6 C7 C2 121.7(7) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
O2 C8 O1 120.9(7) . . ?
O2 C8 C4 120.7(7) . . ?
O1 C8 C4 118.3(7) . . ?
O2 C8 Mn1 63.5(4) . 8_566 ?
O1 C8 Mn1 57.4(4) . 8_566 ?
C4 C8 Mn1 175.6(5) . 8_566 ?
O4 C9 O3 123.4(7) . . ?
O4 C9 C6 120.6(7) . . ?
O3 C9 C6 115.8(7) . . ?
O4 C9 Na1 46.8(4) . 4 ?
O3 C9 Na1 83.5(5) . 4 ?
C6 C9 Na1 144.9(5) . 4 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 2.4(8) . . . . ?
Na1 N1 N2 N3 -162.4(5) . . . . ?
C1 N1 N2 Mn1 -167.5(5) . . . . ?
Na1 N1 N2 Mn1 27.7(7) . . . . ?
N1 N2 N3 N4 -1.6(9) . . . . ?
Mn1 N2 N3 N4 168.2(5) . . . . ?
N2 N3 N4 C1 0.1(8) . . . . ?
N2 N1 C1 N4 -2.4(8) . . . . ?
Na1 N1 C1 N4 156.2(6) . . . . ?
N2 N1 C1 C2 176.8(7) . . . . ?
Na1 N1 C1 C2 -24.6(12) . . . . ?
N3 N4 C1 N1 1.4(8) . . . . ?
N3 N4 C1 C2 -177.8(7) . . . . ?
N1 C1 C2 C3 173.1(7) . . . . ?
N4 C1 C2 C3 -7.8(11) . . . . ?
N1 C1 C2 C7 -4.5(11) . . . . ?
N4 C1 C2 C7 174.6(7) . . . . ?
C7 C2 C3 C4 0.5(10) . . . . ?
C1 C2 C3 C4 -177.2(7) . . . . ?
C2 C3 C4 C5 0.5(11) . . . . ?
C2 C3 C4 C8 174.6(6) . . . . ?
C3 C4 C5 C6 -1.4(11) . . . . ?
C8 C4 C5 C6 -175.5(7) . . . . ?
C4 C5 C6 C7 1.4(11) . . . . ?
C4 C5 C6 C9 177.0(7) . . . . ?
C5 C6 C7 C2 -0.3(11) . . . . ?
C9 C6 C7 C2 -175.9(7) . . . . ?
C3 C2 C7 C6 -0.6(11) . . . . ?
C1 C2 C7 C6 177.1(7) . . . . ?
Mn1 O2 C8 O1 -1.2(8) 8_566 . . . ?
Na1 O2 C8 O1 -81.2(10) 5_676 . . . ?
Mn1 O2 C8 C4 -178.6(6) 8_566 . . . ?
Na1 O2 C8 C4 101.3(7) 5_676 . . . ?
Na1 O2 C8 Mn1 -80.0(5) 5_676 . . 8_566 ?
Mn1 O1 C8 O2 1.2(8) 8_566 . . . ?
Na1 O1 C8 O2 119.4(7) 8_566 . . . ?
Mn1 O1 C8 C4 178.8(6) 8_566 . . . ?
Na1 O1 C8 C4 -63.1(9) 8_566 . . . ?
Na1 O1 C8 Mn1 118.1(6) 8_566 . . 8_566 ?
C5 C4 C8 O2 -2.3(11) . . . . ?
C3 C4 C8 O2 -176.4(7) . . . . ?
C5 C4 C8 O1 -179.9(7) . . . . ?
C3 C4 C8 O1 6.1(11) . . . . ?
Na1 O4 C9 O3 -36.3(10) 4 . . . ?
Na1 O4 C9 C6 138.5(6) 4 . . . ?
Mn1 O3 C9 O4 -25.5(13) 1_565 . . . ?
Mn1 O3 C9 C6 159.5(5) 1_565 . . . ?
Mn1 O3 C9 Na1 -51.2(7) 1_565 . . 4 ?
C7 C6 C9 O4 -0.4(12) . . . . ?
C5 C6 C9 O4 -175.9(7) . . . . ?
C7 C6 C9 O3 174.8(7) . . . . ?
C5 C6 C9 O3 -0.8(11) . . . . ?
C7 C6 C9 Na1 56.8(12) . . . 4 ?
C5 C6 C9 Na1 -118.8(9) . . . 4 ?

_refine_diff_density_max         0.994
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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 1432834'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-01-20 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            'C18 H38 Mn3 N8 O24'
_chemical_formula_weight         915.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3088(8)
_cell_length_b                   10.1375(10)
_cell_length_c                   12.0815(14)
_cell_angle_alpha                78.884(4)
_cell_angle_beta                 77.512(3)
_cell_angle_gamma                78.615(4)
_cell_volume                     846.18(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             469
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.209
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7131
_exptl_absorpt_correction_T_max  0.8887
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   sadabs
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13197
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3230
_reflns_number_gt                2960
_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 FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+11.9023P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     286
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1982
_refine_ls_wR_factor_gt          0.1956
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.31354(14) 0.54931(10) 0.32290(8) 0.0217(3) Uani 1 1 d . . . . .
Mn2 Mn 0.5000 0.0000 1.0000 0.0223(4) Uani 1 2 d S . P . .
C1 C 0.6234(9) 0.2886(6) 0.2794(5) 0.0195(13) Uani 1 1 d . . . . .
C2 C 0.7071(8) 0.1527(6) 0.3372(5) 0.0155(12) Uani 1 1 d . . . . .
C3 C 0.8207(8) 0.0556(6) 0.2734(5) 0.0182(12) Uani 1 1 d . . . . .
H3 H 0.8441 0.0753 0.1937 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8989(8) -0.0691(5) 0.3266(4) 0.0112(11) Uani 1 1 d . . . . .
C5 C 0.8568(8) -0.1002(5) 0.4478(5) 0.0152(12) Uani 1 1 d . . . . .
H5 H 0.9052 -0.1854 0.4842 0.018 Uiso 1 1 calc R U . . .
C6 C 0.7437(8) -0.0046(6) 0.5133(5) 0.0155(12) Uani 1 1 d . . . . .
C7 C 0.6710(8) 0.1229(6) 0.4570(5) 0.0172(12) Uani 1 1 d . . . . .
H7 H 0.5982 0.1884 0.4998 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7110(8) -0.0384(6) 0.6387(5) 0.0144(11) Uani 1 1 d . . . . .
C9 C 1.0197(9) -0.1756(6) 0.2621(5) 0.0199(13) Uani 1 1 d . . . . .
N1 N 0.6256(9) -0.0304(5) 0.8166(5) 0.0259(12) Uani 1 1 d . . . . .
N2 N 0.6175(8) 0.0451(5) 0.7123(4) 0.0213(11) Uani 1 1 d . . . . .
N3 N 0.7717(8) -0.1621(5) 0.6944(4) 0.0234(12) Uani 1 1 d . . . . .
N4 N 0.7169(9) -0.1535(5) 0.8069(5) 0.0279(13) Uani 1 1 d . . . . .
O1 O 0.6505(7) 0.3113(5) 0.1716(4) 0.0304(11) Uani 1 1 d . . . . .
O2 O 0.5277(7) 0.3716(5) 0.3438(4) 0.0298(11) Uani 1 1 d . . . . .
O3 O 1.0362(7) -0.1558(5) 0.1545(4) 0.0348(13) Uani 1 1 d . . . . .
O4 O 1.1007(7) -0.2791(5) 0.3191(4) 0.0331(12) Uani 1 1 d . . . . .
O5 O 0.5320(8) 0.6778(5) 0.3109(5) 0.0368(13) Uani 1 1 d D . . . .
H5A H 0.636(8) 0.658(8) 0.265(6) 0.055 Uiso 1 1 d D U . . .
H5C H 0.497(11) 0.764(3) 0.296(7) 0.055 Uiso 1 1 d D U . . .
O6 O 0.0909(8) 0.4265(5) 0.3351(5) 0.0382(13) Uani 1 1 d D . . . .
H6A H 0.024(12) 0.464(7) 0.284(6) 0.057 Uiso 1 1 d D U . . .
H6B H 0.125(13) 0.343(3) 0.327(7) 0.057 Uiso 1 1 d D U . . .
O7 O 0.3911(9) 0.5415(6) 0.1364(5) 0.0409(14) Uani 1 1 d D . . . .
H7A H 0.474(10) 0.471(5) 0.128(8) 0.061 Uiso 1 1 d D U . . .
H7C H 0.433(12) 0.610(5) 0.094(7) 0.061 Uiso 1 1 d D U . . .
O8 O 0.6326(8) 0.1826(6) 0.9891(4) 0.0356(12) Uani 1 1 d D . . . .
H8A H 0.737(7) 0.182(10) 0.941(5) 0.053 Uiso 1 1 d D U . . .
H8B H 0.648(11) 0.199(10) 1.052(4) 0.053 Uiso 1 1 d D U . . .
O9 O 0.2646(9) 0.5267(7) 0.5118(5) 0.0502(16) Uani 1 1 d D . . . .
H9A H 0.214(13) 0.465(9) 0.497(9) 0.075 Uiso 1 1 d D U . . .
H9B H 0.191(12) 0.563(10) 0.567(7) 0.075 Uiso 1 1 d D U . . .
O10 O 0.2550(12) 0.1324(10) 0.9471(8) 0.083(3) Uani 1 1 d . . . . .
H10A H 0.25(2) 0.194(15) 0.969(15) 0.125 Uiso 1 1 d D U . . .
H10B H 0.17(2) 0.078(14) 0.989(14) 0.125 Uiso 1 1 d D U . . .
O11 O 0.8717(13) 0.5617(11) 0.1726(8) 0.104(3) Uani 1 1 d . . . . .
O12 O 0.029(3) 0.342(2) 1.0608(17) 0.097(6) Uani 0.5 1 d . . P . .
O12' O 0.214(4) 0.3927(19) 1.0336(18) 0.108(7) Uani 0.5 1 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 O4 2.093(5) 1_465 ?
Mn1 O2 2.154(4) . ?
Mn1 O6 2.201(6) . ?
Mn1 O9 2.206(6) . ?
Mn1 O7 2.214(5) . ?
Mn1 O5 2.217(6) . ?
Mn1 H9A 2.14(11) . ?
Mn2 O10 2.152(8) 2_657 ?
Mn2 O10 2.152(8) . ?
Mn2 O8 2.223(5) 2_657 ?
Mn2 O8 2.223(5) . ?
Mn2 N1 2.263(5) 2_657 ?
Mn2 N1 2.263(5) . ?
C1 O1 1.258(8) . ?
C1 O2 1.259(7) . ?
C1 C2 1.496(8) . ?
C2 C3 1.395(8) . ?
C2 C7 1.398(8) . ?
C3 C4 1.377(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(8) . ?
C4 C9 1.484(8) . ?
C5 C6 1.395(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(8) . ?
C6 C8 1.465(8) . ?
C7 H7 0.9300 . ?
C8 N2 1.331(7) . ?
C8 N3 1.343(8) . ?
C9 O4 1.256(8) . ?
C9 O3 1.259(8) . ?
N1 N4 1.307(8) . ?
N1 N2 1.348(7) . ?
N3 N4 1.346(7) . ?
O4 Mn1 2.093(5) 1_645 ?
O5 H5A 0.86(2) . ?
O5 H5C 0.86(2) . ?
O6 H6A 0.85(2) . ?
O6 H6B 0.85(2) . ?
O7 H7A 0.85(2) . ?
O7 H7C 0.85(2) . ?
O8 H8A 0.85(2) . ?
O8 H8B 0.85(2) . ?
O9 H9A 0.85(2) . ?
O9 H9B 0.85(2) . ?
O10 H10A 0.71(15) . ?
O10 H10B 0.92(14) . ?
O12 O12' 1.49(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 O2 174.71(19) 1_465 . ?
O4 Mn1 O6 87.4(2) 1_465 . ?
O2 Mn1 O6 92.7(2) . . ?
O4 Mn1 O9 90.0(2) 1_465 . ?
O2 Mn1 O9 84.8(2) . . ?
O6 Mn1 O9 90.1(2) . . ?
O4 Mn1 O7 98.7(2) 1_465 . ?
O2 Mn1 O7 86.60(19) . . ?
O6 Mn1 O7 89.1(2) . . ?
O9 Mn1 O7 171.3(2) . . ?
O4 Mn1 O5 91.1(2) 1_465 . ?
O2 Mn1 O5 88.8(2) . . ?
O6 Mn1 O5 178.50(19) . . ?
O9 Mn1 O5 89.8(2) . . ?
O7 Mn1 O5 91.3(2) . . ?
O4 Mn1 H9A 95(3) 1_465 . ?
O2 Mn1 H9A 80(3) . . ?
O6 Mn1 H9A 68.7(12) . . ?
O9 Mn1 H9A 22.4(6) . . ?
O7 Mn1 H9A 153.0(10) . . ?
O5 Mn1 H9A 111.4(12) . . ?
O10 Mn2 O10 180.0 2_657 . ?
O10 Mn2 O8 88.9(3) 2_657 2_657 ?
O10 Mn2 O8 91.1(3) . 2_657 ?
O10 Mn2 O8 91.1(3) 2_657 . ?
O10 Mn2 O8 88.9(3) . . ?
O8 Mn2 O8 180.0 2_657 . ?
O10 Mn2 N1 91.1(3) 2_657 2_657 ?
O10 Mn2 N1 88.9(3) . 2_657 ?
O8 Mn2 N1 94.39(19) 2_657 2_657 ?
O8 Mn2 N1 85.61(19) . 2_657 ?
O10 Mn2 N1 88.9(3) 2_657 . ?
O10 Mn2 N1 91.1(3) . . ?
O8 Mn2 N1 85.61(19) 2_657 . ?
O8 Mn2 N1 94.39(19) . . ?
N1 Mn2 N1 180.0 2_657 . ?
O1 C1 O2 124.8(5) . . ?
O1 C1 C2 118.4(5) . . ?
O2 C1 C2 116.8(5) . . ?
C3 C2 C7 119.5(5) . . ?
C3 C2 C1 121.1(5) . . ?
C7 C2 C1 119.4(5) . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 C9 122.9(5) . . ?
C5 C4 C9 118.0(5) . . ?
C6 C5 C4 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.9(5) . . ?
C5 C6 C8 119.1(5) . . ?
C7 C6 C8 122.0(5) . . ?
C2 C7 C6 120.6(5) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N2 C8 N3 111.0(5) . . ?
N2 C8 C6 126.0(5) . . ?
N3 C8 C6 123.0(5) . . ?
O4 C9 O3 124.5(6) . . ?
O4 C9 C4 117.3(5) . . ?
O3 C9 C4 118.2(5) . . ?
N4 N1 N2 110.8(5) . . ?
N4 N1 Mn2 113.6(4) . . ?
N2 N1 Mn2 135.3(4) . . ?
C8 N2 N1 104.3(5) . . ?
C8 N3 N4 105.7(5) . . ?
N1 N4 N3 108.1(5) . . ?
C1 O2 Mn1 134.8(4) . . ?
C9 O4 Mn1 148.8(5) . 1_645 ?
Mn1 O5 H5A 116(6) . . ?
Mn1 O5 H5C 116(6) . . ?
H5A O5 H5C 107(3) . . ?
Mn1 O6 H6A 108(6) . . ?
Mn1 O6 H6B 118(6) . . ?
H6A O6 H6B 107(3) . . ?
Mn1 O7 H7A 107(7) . . ?
Mn1 O7 H7C 117(7) . . ?
H7A O7 H7C 109(3) . . ?
Mn2 O8 H8A 112(6) . . ?
Mn2 O8 H8B 116(6) . . ?
H8A O8 H8B 109(3) . . ?
Mn1 O9 H9A 74(7) . . ?
Mn1 O9 H9B 140(8) . . ?
H9A O9 H9B 109(3) . . ?
Mn2 O10 H10A 104(10) . . ?
Mn2 O10 H10B 95(10) . . ?
H10A O10 H10B 115(10) . . ?

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
O1 C1 C2 C3 3.2(9) . . . . ?
O2 C1 C2 C3 -177.8(6) . . . . ?
O1 C1 C2 C7 -176.9(6) . . . . ?
O2 C1 C2 C7 2.0(9) . . . . ?
C7 C2 C3 C4 -0.3(9) . . . . ?
C1 C2 C3 C4 179.5(6) . . . . ?
C2 C3 C4 C5 2.3(9) . . . . ?
C2 C3 C4 C9 179.7(6) . . . . ?
C3 C4 C5 C6 -2.4(9) . . . . ?
C9 C4 C5 C6 -179.9(6) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
C4 C5 C6 C8 -177.1(5) . . . . ?
C3 C2 C7 C6 -1.7(9) . . . . ?
C1 C2 C7 C6 178.4(6) . . . . ?
C5 C6 C7 C2 1.7(9) . . . . ?
C8 C6 C7 C2 179.1(6) . . . . ?
C5 C6 C8 N2 175.2(6) . . . . ?
C7 C6 C8 N2 -2.2(10) . . . . ?
C5 C6 C8 N3 -5.8(9) . . . . ?
C7 C6 C8 N3 176.8(6) . . . . ?
C3 C4 C9 O4 172.2(6) . . . . ?
C5 C4 C9 O4 -10.4(9) . . . . ?
C3 C4 C9 O3 -6.9(9) . . . . ?
C5 C4 C9 O3 170.5(6) . . . . ?
N3 C8 N2 N1 1.3(7) . . . . ?
C6 C8 N2 N1 -179.6(6) . . . . ?
N4 N1 N2 C8 -0.8(7) . . . . ?
Mn2 N1 N2 C8 -174.6(5) . . . . ?
N2 C8 N3 N4 -1.3(7) . . . . ?
C6 C8 N3 N4 179.6(6) . . . . ?
N2 N1 N4 N3 0.0(8) . . . . ?
Mn2 N1 N4 N3 175.3(4) . . . . ?
C8 N3 N4 N1 0.8(7) . . . . ?
O1 C1 O2 Mn1 19.8(11) . . . . ?
C2 C1 O2 Mn1 -159.1(4) . . . . ?
O3 C9 O4 Mn1 16.9(14) . . . 1_645 ?
C4 C9 O4 Mn1 -162.2(6) . . . 1_645 ?

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
O5 H5A O11 0.86(2) 2.02(3) 2.855(11) 165(7) .
O5 H5C N2 0.86(2) 1.94(2) 2.790(7) 169(8) 2_666
O6 H6A O11 0.85(2) 1.93(2) 2.785(11) 176(8) 1_455
O6 H6B N3 0.85(2) 1.89(2) 2.734(7) 173(9) 2_656
O7 H7A O1 0.85(2) 1.92(4) 2.728(7) 158(9) .
O7 H7C O8 0.85(2) 2.16(5) 2.905(8) 147(8) 2_666
O8 H8A O3 0.85(2) 1.81(2) 2.655(7) 173(10) 2_756
O8 H8B O1 0.85(2) 2.01(4) 2.807(7) 158(9) 1_556
O8 H8B O1 0.85(2) 2.01(4) 2.807(7) 158(9) 1_556
O9 H9B O2 0.85(2) 2.76(10) 2.978(9) 96(7) 2_666
O9 H9B O6 0.85(2) 2.14(6) 2.859(8) 142(8) 2_566
O10 H10A O12' 0.71(15) 2.25(15) 2.96(2) 175(18) .

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.129

