# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global


data_z
#TrackingRef '1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Mn2 N14 O4'
_chemical_formula_weight         604.34

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   23.746(8)
_cell_length_b                   12.946(4)
_cell_length_c                   15.957(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4905(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    1.087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8120
_exptl_absorpt_correction_T_max  0.8716
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2011)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49835
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5629
_reflns_number_gt                4617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+6.3302P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5629
_refine_ls_number_parameters     361
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.522825(18) 0.21230(4) 0.11317(3) 0.03038(14) Uani 1 1 d . . .
Mn2 Mn 0.269050(19) 0.10617(4) -0.00940(3) 0.03338(14) Uani 1 1 d . . .
C1 C 0.76167(13) 0.1313(2) 0.0059(2) 0.0347(7) Uani 1 1 d . . .
H1 H 0.7992 0.1152 -0.0046 0.042 Uiso 1 1 calc R . .
C2 C 0.68666(12) 0.2127(2) 0.0282(2) 0.0289(6) Uani 1 1 d . . .
C3 C 0.65141(12) 0.3031(2) 0.0450(2) 0.0316(7) Uani 1 1 d . . .
C4 C 0.58995(13) 0.4113(2) 0.0785(2) 0.0344(7) Uani 1 1 d . . .
C5 C 0.53589(13) 0.4549(3) 0.1048(2) 0.0364(7) Uani 1 1 d . . .
C6 C 0.52568(16) 0.5605(3) 0.1049(3) 0.0517(10) Uani 1 1 d . . .
H6 H 0.5536 0.6067 0.0884 0.062 Uiso 1 1 calc R . .
C7 C 0.47356(18) 0.5959(3) 0.1299(3) 0.0619(12) Uani 1 1 d . . .
H7 H 0.4656 0.6662 0.1295 0.074 Uiso 1 1 calc R . .
C8 C 0.43349(18) 0.5260(4) 0.1553(3) 0.0693(14) Uani 1 1 d . . .
H8 H 0.3982 0.5483 0.1731 0.083 Uiso 1 1 calc R . .
C9 C 0.44657(16) 0.4225(3) 0.1539(3) 0.0594(12) Uani 1 1 d . . .
H9 H 0.4193 0.3755 0.1711 0.071 Uiso 1 1 calc R . .
C10 C 0.37454(16) 0.1369(4) 0.2725(2) 0.0648(13) Uani 1 1 d . . .
H10 H 0.3533 0.1234 0.3202 0.078 Uiso 1 1 calc R . .
C11 C 0.39860(12) 0.1550(3) 0.1485(2) 0.0336(7) Uani 1 1 d . . .
C12 C 0.40149(12) 0.1626(2) 0.0575(2) 0.0311(6) Uani 1 1 d . . .
C13 C 0.38689(14) 0.1642(3) -0.0712(2) 0.0354(7) Uani 1 1 d . . .
C14 C 0.35707(16) 0.1546(3) -0.1519(2) 0.0433(8) Uani 1 1 d . . .
C15 C 0.3825(2) 0.1717(4) -0.2280(3) 0.0699(13) Uani 1 1 d . . .
H15 H 0.4204 0.1896 -0.2307 0.084 Uiso 1 1 calc R . .
C16 C 0.3514(3) 0.1620(5) -0.2998(3) 0.0897(18) Uani 1 1 d . . .
H16 H 0.3680 0.1727 -0.3519 0.108 Uiso 1 1 calc R . .
C17 C 0.2958(3) 0.1366(5) -0.2943(3) 0.0864(17) Uani 1 1 d . . .
H17 H 0.2739 0.1308 -0.3423 0.104 Uiso 1 1 calc R . .
C18 C 0.2728(2) 0.1199(4) -0.2170(3) 0.0660(13) Uani 1 1 d . . .
H18 H 0.2350 0.1020 -0.2136 0.079 Uiso 1 1 calc R . .
N1 N 0.74244(11) 0.2280(2) 0.01313(19) 0.0360(6) Uani 1 1 d . . .
N2 N 0.67210(10) 0.11453(19) 0.02929(17) 0.0306(5) Uani 1 1 d . . .
N3 N 0.72169(10) 0.06073(19) 0.01512(17) 0.0310(6) Uani 1 1 d . . .
N4 N 0.59661(10) 0.30795(18) 0.06707(17) 0.0299(5) Uani 1 1 d . . .
N5 N 0.67627(11) 0.3958(2) 0.0429(2) 0.0433(7) Uani 1 1 d . . .
N6 N 0.63600(12) 0.4668(2) 0.0652(2) 0.0478(8) Uani 1 1 d . . .
N7 N 0.49698(12) 0.3858(2) 0.1287(2) 0.0402(7) Uani 1 1 d . . .
N8 N 0.35295(12) 0.1318(3) 0.1947(2) 0.0583(10) Uani 1 1 d . . .
N9 N 0.44462(10) 0.1732(2) 0.19297(17) 0.0352(6) Uani 1 1 d . . .
N10 N 0.42852(12) 0.1626(3) 0.27590(18) 0.0460(7) Uani 1 1 d . . .
N11 N 0.35998(10) 0.1464(2) 0.00269(17) 0.0326(6) Uani 1 1 d . . .
N12 N 0.45021(11) 0.1890(2) 0.02222(17) 0.0360(6) Uani 1 1 d . . .
N13 N 0.44060(12) 0.1894(2) -0.06288(17) 0.0393(7) Uani 1 1 d . . .
N14 N 0.30244(14) 0.1279(2) -0.14563(19) 0.0453(7) Uani 1 1 d . . .
O1 O 0.55816(10) 0.0772(2) 0.04520(19) 0.0487(6) Uani 1 1 d D . .
H1A H 0.5945(8) 0.078(4) 0.045(3) 0.073 Uiso 1 1 d D . .
H1B H 0.5474(17) 0.076(4) -0.0052(15) 0.073 Uiso 1 1 d D . .
O2 O 0.25095(11) 0.1000(3) 0.12657(17) 0.0537(7) Uani 1 1 d D . .
H2A H 0.2812(11) 0.112(4) 0.152(3) 0.081 Uiso 1 1 d D . .
H2B H 0.2220(11) 0.101(4) 0.155(3) 0.081 Uiso 1 1 d D . .
O3 O 0.5285(2) 0.0776(6) -0.1336(4) 0.135(2) Uani 1 1 d D . .
H3B H 0.515(4) 0.065(8) -0.186(3) 0.202 Uiso 1 1 d D . .
H3A H 0.501(3) 0.119(7) -0.115(5) 0.202 Uiso 1 1 d D . .
O4 O 0.1839(3) 0.0946(5) 0.2882(4) 0.165(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.0212(2) 0.0336(3) 0.0363(3) 0.0027(2) -0.00122(18) -0.00258(18)
Mn2 0.0262(2) 0.0213(2) 0.0527(3) -0.0014(2) -0.0113(2) 0.00208(18)
C1 0.0267(15) 0.0279(15) 0.0494(19) -0.0010(13) 0.0042(13) 0.0040(12)
C2 0.0253(13) 0.0236(14) 0.0379(16) 0.0002(12) 0.0060(12) -0.0006(11)
C3 0.0235(13) 0.0256(15) 0.0456(18) -0.0008(13) 0.0090(13) -0.0001(11)
C4 0.0294(15) 0.0247(15) 0.0490(19) 0.0016(13) 0.0078(14) 0.0030(12)
C5 0.0309(15) 0.0306(16) 0.0476(19) -0.0005(14) 0.0048(14) 0.0047(13)
C6 0.047(2) 0.0327(19) 0.075(3) 0.0014(18) 0.0133(19) 0.0056(16)
C7 0.054(2) 0.044(2) 0.088(3) -0.005(2) 0.011(2) 0.0222(19)
C8 0.040(2) 0.061(3) 0.107(4) -0.004(3) 0.022(2) 0.021(2)
C9 0.0333(18) 0.047(2) 0.097(3) 0.001(2) 0.021(2) 0.0089(17)
C10 0.0353(18) 0.122(4) 0.037(2) -0.008(2) 0.0026(16) -0.026(2)
C11 0.0234(14) 0.0428(18) 0.0347(16) -0.0022(14) -0.0004(12) -0.0041(13)
C12 0.0242(14) 0.0326(16) 0.0366(17) 0.0007(13) -0.0039(12) -0.0009(12)
C13 0.0375(17) 0.0328(17) 0.0359(17) 0.0013(13) -0.0039(14) 0.0020(13)
C14 0.053(2) 0.0387(19) 0.0381(18) 0.0013(15) -0.0087(16) 0.0010(16)
C15 0.071(3) 0.102(4) 0.038(2) 0.004(2) -0.001(2) -0.001(3)
C16 0.108(5) 0.125(5) 0.037(2) 0.003(3) -0.011(3) 0.002(4)
C17 0.115(5) 0.097(4) 0.047(3) -0.006(3) -0.040(3) -0.007(4)
C18 0.074(3) 0.067(3) 0.057(3) -0.001(2) -0.031(2) -0.014(2)
N1 0.0271(12) 0.0221(13) 0.0589(18) -0.0004(11) 0.0107(12) -0.0018(10)
N2 0.0279(12) 0.0221(12) 0.0417(15) -0.0007(10) 0.0024(11) 0.0004(10)
N3 0.0273(12) 0.0218(12) 0.0439(15) -0.0011(11) -0.0003(11) 0.0032(10)
N4 0.0252(12) 0.0207(12) 0.0437(15) -0.0005(10) 0.0064(11) 0.0005(9)
N5 0.0286(13) 0.0223(13) 0.079(2) -0.0015(13) 0.0178(14) -0.0007(11)
N6 0.0331(14) 0.0248(14) 0.085(2) -0.0034(14) 0.0186(15) -0.0002(11)
N7 0.0275(13) 0.0373(15) 0.0557(18) 0.0004(13) 0.0069(12) 0.0028(12)
N8 0.0320(15) 0.104(3) 0.0391(17) -0.0098(18) 0.0022(13) -0.0221(17)
N9 0.0264(12) 0.0464(16) 0.0329(14) 0.0008(12) -0.0021(10) -0.0046(11)
N10 0.0323(14) 0.073(2) 0.0326(15) -0.0062(14) -0.0002(12) -0.0103(15)
N11 0.0269(12) 0.0327(14) 0.0382(14) -0.0015(11) -0.0052(11) -0.0010(11)
N12 0.0270(13) 0.0448(16) 0.0361(14) 0.0004(12) -0.0007(11) -0.0029(11)
N13 0.0374(15) 0.0477(17) 0.0328(14) 0.0029(12) 0.0006(12) -0.0031(13)
N14 0.0519(18) 0.0405(16) 0.0435(16) -0.0009(13) -0.0173(14) -0.0025(14)
O1 0.0323(12) 0.0432(14) 0.0705(18) -0.0126(14) -0.0021(12) -0.0024(11)
O2 0.0317(12) 0.075(2) 0.0544(16) -0.0079(14) -0.0008(12) -0.0033(14)
O3 0.107(4) 0.169(6) 0.129(4) -0.004(4) 0.041(3) 0.033(4)
O4 0.179(6) 0.157(6) 0.159(6) 0.015(4) 0.015(5) -0.006(4)

_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 N10 2.209(3) 4_655 ?
Mn1 O1 2.222(3) . ?
Mn1 N4 2.268(2) . ?
Mn1 N12 2.274(3) . ?
Mn1 N9 2.308(3) . ?
Mn1 N7 2.341(3) . ?
Mn2 N3 2.174(3) 5_655 ?
Mn2 O2 2.213(3) . ?
Mn2 N11 2.229(3) . ?
Mn2 N1 2.238(3) 3_455 ?
Mn2 N5 2.267(3) 3_455 ?
Mn2 N14 2.331(3) . ?
C1 N3 1.326(4) . ?
C1 N1 1.338(4) . ?
C1 H1 0.9300 . ?
C2 N2 1.317(4) . ?
C2 N1 1.361(4) . ?
C2 C3 1.464(4) . ?
C3 N5 1.338(4) . ?
C3 N4 1.349(4) . ?
C4 N6 1.326(4) . ?
C4 N4 1.360(4) . ?
C4 C5 1.464(4) . ?
C5 N7 1.341(4) . ?
C5 C6 1.389(5) . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 N7 1.349(4) . ?
C9 H9 0.9300 . ?
C10 N10 1.326(4) . ?
C10 N8 1.345(5) . ?
C10 H10 0.9300 . ?
C11 N9 1.324(4) . ?
C11 N8 1.345(4) . ?
C11 C12 1.456(4) . ?
C12 N12 1.331(4) . ?
C12 N11 1.335(4) . ?
C13 N13 1.323(4) . ?
C13 N11 1.361(4) . ?
C13 C14 1.474(5) . ?
C14 N14 1.346(5) . ?
C14 C15 1.374(6) . ?
C15 C16 1.371(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(7) . ?
C17 H17 0.9300 . ?
C18 N14 1.342(5) . ?
C18 H18 0.9300 . ?
N1 Mn2 2.238(3) 3 ?
N2 N3 1.386(3) . ?
N3 Mn2 2.174(3) 5_655 ?
N5 N6 1.373(4) . ?
N5 Mn2 2.267(3) 3 ?
N9 N10 1.384(4) . ?
N10 Mn1 2.209(3) 4_655 ?
N12 N13 1.377(4) . ?
O1 H1A 0.862(18) . ?
O1 H1B 0.844(18) . ?
O2 H2A 0.843(18) . ?
O2 H2B 0.825(18) . ?
O3 H3B 0.90(2) . ?
O3 H3A 0.90(2) . ?

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
N10 Mn1 O1 87.96(12) 4_655 . ?
N10 Mn1 N4 90.85(11) 4_655 . ?
O1 Mn1 N4 88.84(9) . . ?
N10 Mn1 N12 150.37(12) 4_655 . ?
O1 Mn1 N12 82.56(10) . . ?
N4 Mn1 N12 116.82(10) . . ?
N10 Mn1 N9 85.12(10) 4_655 . ?
O1 Mn1 N9 113.61(10) . . ?
N4 Mn1 N9 156.97(10) . . ?
N12 Mn1 N9 73.31(10) . . ?
N10 Mn1 N7 109.35(12) 4_655 . ?
O1 Mn1 N7 154.89(11) . . ?
N4 Mn1 N7 73.33(9) . . ?
N12 Mn1 N7 89.78(11) . . ?
N9 Mn1 N7 86.62(10) . . ?
N3 Mn2 O2 91.44(11) 5_655 . ?
N3 Mn2 N11 97.92(10) 5_655 . ?
O2 Mn2 N11 96.41(10) . . ?
N3 Mn2 N1 168.70(9) 5_655 3_455 ?
O2 Mn2 N1 90.32(12) . 3_455 ?
N11 Mn2 N1 92.97(10) . 3_455 ?
N3 Mn2 N5 94.42(10) 5_655 3_455 ?
O2 Mn2 N5 92.39(12) . 3_455 ?
N11 Mn2 N5 164.63(11) . 3_455 ?
N1 Mn2 N5 74.36(10) 3_455 3_455 ?
N3 Mn2 N14 92.66(10) 5_655 . ?
O2 Mn2 N14 169.93(10) . . ?
N11 Mn2 N14 73.92(10) . . ?
N1 Mn2 N14 87.45(11) 3_455 . ?
N5 Mn2 N14 96.45(12) 3_455 . ?
N3 C1 N1 113.0(3) . . ?
N3 C1 H1 123.5 . . ?
N1 C1 H1 123.5 . . ?
N2 C2 N1 113.5(3) . . ?
N2 C2 C3 128.2(3) . . ?
N1 C2 C3 118.2(3) . . ?
N5 C3 N4 113.0(3) . . ?
N5 C3 C2 117.4(3) . . ?
N4 C3 C2 129.5(3) . . ?
N6 C4 N4 114.6(3) . . ?
N6 C4 C5 124.1(3) . . ?
N4 C4 C5 121.3(3) . . ?
N7 C5 C6 122.4(3) . . ?
N7 C5 C4 115.4(3) . . ?
C6 C5 C4 122.2(3) . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 118.7(4) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
N7 C9 C8 123.3(4) . . ?
N7 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N10 C10 N8 114.7(3) . . ?
N10 C10 H10 122.6 . . ?
N8 C10 H10 122.6 . . ?
N9 C11 N8 114.2(3) . . ?
N9 C11 C12 118.9(3) . . ?
N8 C11 C12 126.8(3) . . ?
N12 C12 N11 113.9(3) . . ?
N12 C12 C11 118.7(3) . . ?
N11 C12 C11 127.4(3) . . ?
N13 C13 N11 114.0(3) . . ?
N13 C13 C14 124.9(3) . . ?
N11 C13 C14 121.1(3) . . ?
N14 C14 C15 122.1(4) . . ?
N14 C14 C13 114.8(3) . . ?
C15 C14 C13 123.1(4) . . ?
C16 C15 C14 119.1(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 118.9(4) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N14 C18 C17 123.0(5) . . ?
N14 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C1 N1 C2 102.2(2) . . ?
C1 N1 Mn2 143.0(2) . 3 ?
C2 N1 Mn2 114.81(19) . 3 ?
C2 N2 N3 105.0(2) . . ?
C1 N3 N2 106.3(2) . . ?
C1 N3 Mn2 127.4(2) . 5_655 ?
N2 N3 Mn2 126.30(18) . 5_655 ?
C3 N4 C4 101.1(2) . . ?
C3 N4 Mn1 143.5(2) . . ?
C4 N4 Mn1 113.82(19) . . ?
C3 N5 N6 106.6(2) . . ?
C3 N5 Mn2 115.1(2) . 3 ?
N6 N5 Mn2 138.2(2) . 3 ?
C4 N6 N5 104.7(3) . . ?
C5 N7 C9 117.4(3) . . ?
C5 N7 Mn1 115.4(2) . . ?
C9 N7 Mn1 127.0(3) . . ?
C10 N8 C11 100.9(3) . . ?
C11 N9 N10 105.5(2) . . ?
C11 N9 Mn1 114.0(2) . . ?
N10 N9 Mn1 140.5(2) . . ?
C10 N10 N9 104.6(3) . . ?
C10 N10 Mn1 127.7(2) . 4_655 ?
N9 N10 Mn1 126.4(2) . 4_655 ?
C12 N11 C13 101.2(3) . . ?
C12 N11 Mn2 144.0(2) . . ?
C13 N11 Mn2 114.8(2) . . ?
C12 N12 N13 105.9(3) . . ?
C12 N12 Mn1 115.0(2) . . ?
N13 N12 Mn1 139.0(2) . . ?
C13 N13 N12 105.0(3) . . ?
C18 N14 C14 117.5(4) . . ?
C18 N14 Mn2 127.1(3) . . ?
C14 N14 Mn2 115.3(2) . . ?
Mn1 O1 H1A 111(3) . . ?
Mn1 O1 H1B 112(3) . . ?
H1A O1 H1B 108(3) . . ?
Mn2 O2 H2A 108(3) . . ?
Mn2 O2 H2B 135(3) . . ?
H2A O2 H2B 116(3) . . ?
H3B O3 H3A 99(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 N5 177.8(3) . . . . ?
N1 C2 C3 N5 1.3(5) . . . . ?
N2 C2 C3 N4 1.4(6) . . . . ?
N1 C2 C3 N4 -175.0(3) . . . . ?
N6 C4 C5 N7 -169.2(4) . . . . ?
N4 C4 C5 N7 9.7(5) . . . . ?
N6 C4 C5 C6 10.8(6) . . . . ?
N4 C4 C5 C6 -170.3(4) . . . . ?
N7 C5 C6 C7 -0.5(6) . . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C5 C6 C7 C8 1.1(7) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C7 C8 C9 N7 0.0(8) . . . . ?
N9 C11 C12 N12 -0.9(5) . . . . ?
N8 C11 C12 N12 178.4(4) . . . . ?
N9 C11 C12 N11 179.4(3) . . . . ?
N8 C11 C12 N11 -1.3(6) . . . . ?
N13 C13 C14 N14 179.9(3) . . . . ?
N11 C13 C14 N14 0.3(5) . . . . ?
N13 C13 C14 C15 -0.3(6) . . . . ?
N11 C13 C14 C15 -179.9(4) . . . . ?
N14 C14 C15 C16 0.5(8) . . . . ?
C13 C14 C15 C16 -179.3(5) . . . . ?
C14 C15 C16 C17 0.6(9) . . . . ?
C15 C16 C17 C18 -1.0(10) . . . . ?
C16 C17 C18 N14 0.5(9) . . . . ?
N3 C1 N1 C2 0.2(4) . . . . ?
N3 C1 N1 Mn2 -179.9(3) . . . 3 ?
N2 C2 N1 C1 -0.7(4) . . . . ?
C3 C2 N1 C1 176.3(3) . . . . ?
N2 C2 N1 Mn2 179.4(2) . . . 3 ?
C3 C2 N1 Mn2 -3.6(4) . . . 3 ?
N1 C2 N2 N3 0.8(4) . . . . ?
C3 C2 N2 N3 -175.8(3) . . . . ?
N1 C1 N3 N2 0.2(4) . . . . ?
N1 C1 N3 Mn2 -179.8(2) . . . 5_655 ?
C2 N2 N3 C1 -0.6(3) . . . . ?
C2 N2 N3 Mn2 179.4(2) . . . 5_655 ?
N5 C3 N4 C4 -0.2(4) . . . . ?
C2 C3 N4 C4 176.3(3) . . . . ?
N5 C3 N4 Mn1 -163.6(3) . . . . ?
C2 C3 N4 Mn1 12.9(6) . . . . ?
N6 C4 N4 C3 -0.1(4) . . . . ?
C5 C4 N4 C3 -179.1(3) . . . . ?
N6 C4 N4 Mn1 169.2(3) . . . . ?
C5 C4 N4 Mn1 -9.8(4) . . . . ?
N10 Mn1 N4 C3 57.3(4) 4_655 . . . ?
O1 Mn1 N4 C3 -30.6(4) . . . . ?
N12 Mn1 N4 C3 -111.7(4) . . . . ?
N9 Mn1 N4 C3 136.8(4) . . . . ?
N7 Mn1 N4 C3 167.3(4) . . . . ?
N10 Mn1 N4 C4 -104.8(2) 4_655 . . . ?
O1 Mn1 N4 C4 167.3(2) . . . . ?
N12 Mn1 N4 C4 86.2(2) . . . . ?
N9 Mn1 N4 C4 -25.3(4) . . . . ?
N7 Mn1 N4 C4 5.2(2) . . . . ?
N4 C3 N5 N6 0.4(4) . . . . ?
C2 C3 N5 N6 -176.6(3) . . . . ?
N4 C3 N5 Mn2 178.6(2) . . . 3 ?
C2 C3 N5 Mn2 1.6(4) . . . 3 ?
N4 C4 N6 N5 0.3(4) . . . . ?
C5 C4 N6 N5 179.3(3) . . . . ?
C3 N5 N6 C4 -0.4(4) . . . . ?
Mn2 N5 N6 C4 -177.9(3) 3 . . . ?
C6 C5 N7 C9 -0.3(6) . . . . ?
C4 C5 N7 C9 179.7(4) . . . . ?
C6 C5 N7 Mn1 175.7(3) . . . . ?
C4 C5 N7 Mn1 -4.3(4) . . . . ?
C8 C9 N7 C5 0.6(7) . . . . ?
C8 C9 N7 Mn1 -174.9(4) . . . . ?
N10 Mn1 N7 C5 84.6(3) 4_655 . . . ?
O1 Mn1 N7 C5 -46.8(4) . . . . ?
N4 Mn1 N7 C5 -0.3(2) . . . . ?
N12 Mn1 N7 C5 -118.5(3) . . . . ?
N9 Mn1 N7 C5 168.2(3) . . . . ?
N10 Mn1 N7 C9 -99.8(4) 4_655 . . . ?
O1 Mn1 N7 C9 128.8(4) . . . . ?
N4 Mn1 N7 C9 175.3(4) . . . . ?
N12 Mn1 N7 C9 57.1(4) . . . . ?
N9 Mn1 N7 C9 -16.2(4) . . . . ?
N10 C10 N8 C11 1.0(6) . . . . ?
N9 C11 N8 C10 -0.1(5) . . . . ?
C12 C11 N8 C10 -179.4(4) . . . . ?
N8 C11 N9 N10 -0.7(4) . . . . ?
C12 C11 N9 N10 178.6(3) . . . . ?
N8 C11 N9 Mn1 179.8(3) . . . . ?
C12 C11 N9 Mn1 -0.8(4) . . . . ?
N10 Mn1 N9 C11 -158.0(3) 4_655 . . . ?
O1 Mn1 N9 C11 -72.4(3) . . . . ?
N4 Mn1 N9 C11 121.3(3) . . . . ?
N12 Mn1 N9 C11 1.4(2) . . . . ?
N7 Mn1 N9 C11 92.2(2) . . . . ?
N10 Mn1 N9 N10 22.8(3) 4_655 . . . ?
O1 Mn1 N9 N10 108.4(4) . . . . ?
N4 Mn1 N9 N10 -57.9(5) . . . . ?
N12 Mn1 N9 N10 -177.8(4) . . . . ?
N7 Mn1 N9 N10 -87.0(4) . . . . ?
N8 C10 N10 N9 -1.5(6) . . . . ?
N8 C10 N10 Mn1 166.0(3) . . . 4_655 ?
C11 N9 N10 C10 1.3(4) . . . . ?
Mn1 N9 N10 C10 -179.5(3) . . . . ?
C11 N9 N10 Mn1 -166.4(2) . . . 4_655 ?
Mn1 N9 N10 Mn1 12.8(5) . . . 4_655 ?
N12 C12 N11 C13 0.4(4) . . . . ?
C11 C12 N11 C13 -179.9(3) . . . . ?
N12 C12 N11 Mn2 -178.2(3) . . . . ?
C11 C12 N11 Mn2 1.4(6) . . . . ?
N13 C13 N11 C12 0.0(4) . . . . ?
C14 C13 N11 C12 179.6(3) . . . . ?
N13 C13 N11 Mn2 179.1(2) . . . . ?
C14 C13 N11 Mn2 -1.3(4) . . . . ?
N3 Mn2 N11 C12 -89.8(4) 5_655 . . . ?
O2 Mn2 N11 C12 2.6(4) . . . . ?
N1 Mn2 N11 C12 93.3(4) 3_455 . . . ?
N5 Mn2 N11 C12 127.1(5) 3_455 . . . ?
N14 Mn2 N11 C12 179.7(4) . . . . ?
N3 Mn2 N11 C13 91.7(2) 5_655 . . . ?
O2 Mn2 N11 C13 -175.9(2) . . . . ?
N1 Mn2 N11 C13 -85.3(2) 3_455 . . . ?
N5 Mn2 N11 C13 -51.4(5) 3_455 . . . ?
N14 Mn2 N11 C13 1.2(2) . . . . ?
N11 C12 N12 N13 -0.7(4) . . . . ?
C11 C12 N12 N13 179.7(3) . . . . ?
N11 C12 N12 Mn1 -178.1(2) . . . . ?
C11 C12 N12 Mn1 2.2(4) . . . . ?
N10 Mn1 N12 C12 43.1(4) 4_655 . . . ?
O1 Mn1 N12 C12 115.5(2) . . . . ?
N4 Mn1 N12 C12 -159.6(2) . . . . ?
N9 Mn1 N12 C12 -1.9(2) . . . . ?
N7 Mn1 N12 C12 -88.4(2) . . . . ?
N10 Mn1 N12 N13 -133.1(3) 4_655 . . . ?
O1 Mn1 N12 N13 -60.7(3) . . . . ?
N4 Mn1 N12 N13 24.2(4) . . . . ?
N9 Mn1 N12 N13 -178.2(4) . . . . ?
N7 Mn1 N12 N13 95.3(3) . . . . ?
N11 C13 N13 N12 -0.4(4) . . . . ?
C14 C13 N13 N12 -180.0(3) . . . . ?
C12 N12 N13 C13 0.6(4) . . . . ?
Mn1 N12 N13 C13 177.1(3) . . . . ?
C17 C18 N14 C14 0.5(7) . . . . ?
C17 C18 N14 Mn2 178.2(4) . . . . ?
C15 C14 N14 C18 -1.0(6) . . . . ?
C13 C14 N14 C18 178.8(3) . . . . ?
C15 C14 N14 Mn2 -179.0(3) . . . . ?
C13 C14 N14 Mn2 0.8(4) . . . . ?
N3 Mn2 N14 C18 83.7(4) 5_655 . . . ?
O2 Mn2 N14 C18 -162.4(6) . . . . ?
N11 Mn2 N14 C18 -178.9(4) . . . . ?
N1 Mn2 N14 C18 -85.0(4) 3_455 . . . ?
N5 Mn2 N14 C18 -11.1(4) 3_455 . . . ?
N3 Mn2 N14 C14 -98.6(3) 5_655 . . . ?
O2 Mn2 N14 C14 15.4(8) . . . . ?
N11 Mn2 N14 C14 -1.1(2) . . . . ?
N1 Mn2 N14 C14 92.7(3) 3_455 . . . ?
N5 Mn2 N14 C14 166.7(3) 3_455 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.070


_database_code_depnum_ccdc_archive 'CCDC 901457'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global


data_z
#TrackingRef '2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Mn2 N15 O3'
_chemical_formula_weight         641.41

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   19.6971(9)
_cell_length_b                   19.6971(9)
_cell_length_c                   19.9978(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7758.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2608
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8802
_exptl_absorpt_correction_T_max  0.8977
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2011)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33422
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3408
_reflns_number_gt                2979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1077P)^2^+16.6495P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     216
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.10504(3) 1.01786(3) 0.02432(3) 0.0384(2) Uani 1 1 d . . .
C1 C 0.1761(3) 1.2567(2) 0.1079(2) 0.0653(14) Uani 1 1 d . . .
H1 H 0.1615 1.2936 0.0827 0.078 Uiso 1 1 calc R . .
C2 C 0.19548(17) 1.15803(17) 0.13974(17) 0.0378(8) Uani 1 1 d . . .
C3 C 0.19926(17) 1.08502(17) 0.14962(17) 0.0372(7) Uani 1 1 d . . .
C4 C 0.1872(2) 0.97916(18) 0.1477(2) 0.0463(9) Uani 1 1 d . . .
C5 C 0.1625(2) 0.9123(2) 0.1265(2) 0.0572(11) Uani 1 1 d . . .
C6 C 0.1824(4) 0.8520(2) 0.1572(4) 0.106(2) Uani 1 1 d . . .
H6 H 0.2136 0.8523 0.1922 0.127 Uiso 1 1 calc R . .
C7 C 0.1551(5) 0.7923(3) 0.1349(4) 0.130(3) Uani 1 1 d . . .
H7 H 0.1682 0.7515 0.1544 0.156 Uiso 1 1 calc R . .
C8 C 0.1084(4) 0.7920(3) 0.0838(4) 0.100(2) Uani 1 1 d . . .
H8 H 0.0884 0.7519 0.0694 0.120 Uiso 1 1 calc R . .
C9 C 0.0924(3) 0.8531(2) 0.0549(3) 0.0725(14) Uani 1 1 d . . .
H9 H 0.0617 0.8533 0.0195 0.087 Uiso 1 1 calc R . .
C10 C 0.0893(10) 0.0460(9) 0.7182(7) 0.134(6) Uani 0.50 1 d PD . .
H10A H 0.0772 -0.0002 0.7280 0.201 Uiso 0.50 1 calc PR . .
H10B H 0.1337 0.0471 0.6985 0.201 Uiso 0.50 1 calc PR . .
H10C H 0.0570 0.0649 0.6875 0.201 Uiso 0.50 1 calc PR . .
C11 C 0.0423(8) 0.1107(6) 0.8203(7) 0.098(4) Uani 0.50 1 d PD . .
H11A H 0.0155 0.0744 0.8385 0.147 Uiso 0.50 1 calc PR . .
H11B H 0.0135 0.1412 0.7960 0.147 Uiso 0.50 1 calc PR . .
H11C H 0.0643 0.1347 0.8560 0.147 Uiso 0.50 1 calc PR . .
C12 C 0.1562(10) 0.0947(7) 0.8085(7) 0.122(6) Uani 0.50 1 d PD . .
H12 H 0.1956 0.0772 0.7895 0.146 Uiso 0.50 1 calc PR . .
N1 N 0.1665(2) 1.19189(16) 0.08879(17) 0.0585(10) Uani 1 1 d . . .
N2 N 0.22080(15) 1.19863(14) 0.18682(15) 0.0408(7) Uani 1 1 d . . .
N3 N 0.20823(18) 1.26339(15) 0.16586(16) 0.0497(8) Uani 1 1 d . . .
N4 N 0.17066(15) 1.03598(14) 0.11216(15) 0.0394(7) Uani 1 1 d . . .
N5 N 0.22361(19) 0.99158(16) 0.20199(18) 0.0556(9) Uani 1 1 d . . .
N6 N 0.23178(17) 1.06108(15) 0.20283(16) 0.0484(8) Uani 1 1 d . . .
N7 N 0.11885(18) 0.91274(16) 0.07504(18) 0.0518(8) Uani 1 1 d . . .
N8 N 0.0894(9) 0.0849(5) 0.7789(6) 0.124(5) Uani 0.50 1 d PD . .
O1 O 0.1078(2) 1.12075(16) -0.01524(16) 0.0667(9) Uani 1 1 d D . .
H1A H 0.127(3) 1.141(3) 0.0180(17) 0.100 Uiso 1 1 d D . .
H1B H 0.133(2) 1.126(3) -0.0496(16) 0.100 Uiso 1 1 d D . .
O2 O 0.1566(9) 0.1257(4) 0.8574(4) 0.166(7) Uani 0.50 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.0331(3) 0.0446(4) 0.0374(4) -0.0176(2) -0.0015(2) 0.0011(2)
C1 0.106(4) 0.035(2) 0.055(3) -0.0008(17) -0.047(3) 0.001(2)
C2 0.0406(18) 0.0360(18) 0.0368(18) -0.0019(14) -0.0116(14) -0.0013(14)
C3 0.0370(17) 0.0364(18) 0.0382(19) -0.0070(14) -0.0086(14) -0.0002(13)
C4 0.053(2) 0.0326(19) 0.054(2) -0.0024(16) -0.0099(17) 0.0035(15)
C5 0.072(3) 0.033(2) 0.067(3) -0.0075(18) -0.010(2) -0.0002(18)
C6 0.165(7) 0.036(3) 0.118(5) 0.006(3) -0.049(5) 0.000(3)
C7 0.218(9) 0.035(3) 0.137(6) 0.004(3) -0.047(7) -0.007(4)
C8 0.148(6) 0.042(3) 0.110(5) -0.016(3) -0.012(4) -0.023(3)
C9 0.089(4) 0.049(3) 0.079(3) -0.022(2) 0.004(3) -0.016(2)
C10 0.171(18) 0.129(14) 0.101(12) -0.012(10) 0.022(11) 0.020(12)
C11 0.134(12) 0.078(8) 0.081(8) -0.005(6) 0.034(8) 0.016(7)
C12 0.176(17) 0.073(9) 0.117(13) 0.040(9) 0.051(12) 0.025(10)
N1 0.089(3) 0.0379(17) 0.0485(19) -0.0022(14) -0.0371(18) -0.0010(16)
N2 0.0498(17) 0.0311(15) 0.0416(17) -0.0014(12) -0.0188(13) -0.0031(12)
N3 0.070(2) 0.0316(15) 0.0477(18) -0.0014(13) -0.0279(16) 0.0001(14)
N4 0.0411(16) 0.0337(15) 0.0433(17) -0.0061(12) -0.0082(13) 0.0004(12)
N5 0.072(2) 0.0344(17) 0.061(2) -0.0008(15) -0.0247(18) 0.0043(15)
N6 0.060(2) 0.0358(17) 0.0491(19) -0.0017(13) -0.0245(15) 0.0008(14)
N7 0.060(2) 0.0399(17) 0.056(2) -0.0135(15) 0.0022(16) -0.0076(14)
N8 0.216(16) 0.063(6) 0.093(8) -0.013(6) 0.064(10) 0.005(8)
O1 0.098(3) 0.0501(18) 0.0524(18) -0.0111(14) -0.0215(17) -0.0007(16)
O2 0.42(2) 0.046(4) 0.038(4) -0.004(3) 0.065(7) 0.018(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.176(3) . ?
Mn1 N4 2.210(3) . ?
Mn1 N3 2.216(3) 14_465 ?
Mn1 N2 2.245(3) 6_554 ?
Mn1 N6 2.298(3) 6_554 ?
Mn1 N7 2.322(4) . ?
C1 N3 1.326(5) . ?
C1 N1 1.346(5) . ?
C1 H1 0.9300 . ?
C2 N2 1.332(4) . ?
C2 N1 1.345(5) . ?
C2 C3 1.454(5) . ?
C3 N6 1.328(4) . ?
C3 N4 1.346(4) . ?
C4 N5 1.324(5) . ?
C4 N4 1.365(5) . ?
C4 C5 1.467(5) . ?
C5 N7 1.341(6) . ?
C5 C6 1.394(7) . ?
C6 C7 1.369(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(8) . ?
C8 H8 0.9300 . ?
C9 N7 1.347(5) . ?
C9 H9 0.9300 . ?
C10 N8 1.436(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N8 1.342(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.153(14) . ?
C12 N8 1.457(15) . ?
C12 H12 0.9300 . ?
N2 N3 1.365(4) . ?
N2 Mn1 2.245(3) 4_465 ?
N3 Mn1 2.216(3) 16_665 ?
N5 N6 1.378(4) . ?
N6 Mn1 2.298(3) 4_465 ?
O1 H1A 0.856(10) . ?
O1 H1B 0.852(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 N4 97.12(11) . . ?
O1 Mn1 N3 91.07(14) . 14_465 ?
N4 Mn1 N3 90.74(11) . 14_465 ?
O1 Mn1 N2 96.49(12) . 6_554 ?
N4 Mn1 N2 164.10(11) . 6_554 ?
N3 Mn1 N2 97.18(11) 14_465 6_554 ?
O1 Mn1 N6 92.52(14) . 6_554 ?
N4 Mn1 N6 97.12(11) . 6_554 ?
N3 Mn1 N6 170.89(11) 14_465 6_554 ?
N2 Mn1 N6 74.09(10) 6_554 6_554 ?
O1 Mn1 N7 170.55(13) . . ?
N4 Mn1 N7 74.23(11) . . ?
N3 Mn1 N7 92.82(13) 14_465 . ?
N2 Mn1 N7 91.57(12) 6_554 . ?
N6 Mn1 N7 84.93(13) 6_554 . ?
N3 C1 N1 114.2(3) . . ?
N3 C1 H1 122.9 . . ?
N1 C1 H1 122.9 . . ?
N2 C2 N1 113.4(3) . . ?
N2 C2 C3 118.6(3) . . ?
N1 C2 C3 128.0(3) . . ?
N6 C3 N4 113.1(3) . . ?
N6 C3 C2 119.0(3) . . ?
N4 C3 C2 127.8(3) . . ?
N5 C4 N4 113.9(3) . . ?
N5 C4 C5 125.6(4) . . ?
N4 C4 C5 120.5(3) . . ?
N7 C5 C6 121.6(4) . . ?
N7 C5 C4 115.4(4) . . ?
C6 C5 C4 123.0(4) . . ?
C7 C6 C5 118.5(6) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 117.7(5) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
N7 C9 C8 123.3(5) . . ?
N7 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N8 C10 H10A 109.5 . . ?
N8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N8 114.9(16) . . ?
O2 C12 H12 122.6 . . ?
N8 C12 H12 122.6 . . ?
C2 N1 C1 101.2(3) . . ?
C2 N2 N3 106.0(3) . . ?
C2 N2 Mn1 115.0(2) . 4_465 ?
N3 N2 Mn1 139.0(2) . 4_465 ?
C1 N3 N2 105.2(3) . . ?
C1 N3 Mn1 130.8(3) . 16_665 ?
N2 N3 Mn1 123.8(2) . 16_665 ?
C3 N4 C4 101.5(3) . . ?
C3 N4 Mn1 143.4(2) . . ?
C4 N4 Mn1 114.9(2) . . ?
C4 N5 N6 104.9(3) . . ?
C3 N6 N5 106.6(3) . . ?
C3 N6 Mn1 113.1(2) . 4_465 ?
N5 N6 Mn1 139.3(2) . 4_465 ?
C5 N7 C9 118.2(4) . . ?
C5 N7 Mn1 114.6(2) . . ?
C9 N7 Mn1 127.0(3) . . ?
C11 N8 C10 136.3(17) . . ?
C11 N8 C12 108.8(13) . . ?
C10 N8 C12 114.6(14) . . ?
Mn1 O1 H1A 99(4) . . ?
Mn1 O1 H1B 114(4) . . ?
H1A O1 H1B 109.0(17) . . ?

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
N2 C2 C3 N6 -4.5(5) . . . . ?
N1 C2 C3 N6 178.4(4) . . . . ?
N2 C2 C3 N4 172.3(4) . . . . ?
N1 C2 C3 N4 -4.8(7) . . . . ?
N5 C4 C5 N7 171.2(4) . . . . ?
N4 C4 C5 N7 -6.0(6) . . . . ?
N5 C4 C5 C6 -8.5(8) . . . . ?
N4 C4 C5 C6 174.2(5) . . . . ?
N7 C5 C6 C7 -1.5(11) . . . . ?
C4 C5 C6 C7 178.2(7) . . . . ?
C5 C6 C7 C8 -0.8(14) . . . . ?
C6 C7 C8 C9 2.3(13) . . . . ?
C7 C8 C9 N7 -1.6(11) . . . . ?
N2 C2 N1 C1 0.2(5) . . . . ?
C3 C2 N1 C1 177.5(4) . . . . ?
N3 C1 N1 C2 -0.1(6) . . . . ?
N1 C2 N2 N3 -0.3(5) . . . . ?
C3 C2 N2 N3 -177.8(3) . . . . ?
N1 C2 N2 Mn1 178.7(3) . . . 4_465 ?
C3 C2 N2 Mn1 1.2(4) . . . 4_465 ?
N1 C1 N3 N2 -0.1(6) . . . . ?
N1 C1 N3 Mn1 -175.3(3) . . . 16_665 ?
C2 N2 N3 C1 0.2(5) . . . . ?
Mn1 N2 N3 C1 -178.4(4) 4_465 . . . ?
C2 N2 N3 Mn1 175.9(3) . . . 16_665 ?
Mn1 N2 N3 Mn1 -2.8(6) 4_465 . . 16_665 ?
N6 C3 N4 C4 1.2(4) . . . . ?
C2 C3 N4 C4 -175.8(4) . . . . ?
N6 C3 N4 Mn1 175.0(3) . . . . ?
C2 C3 N4 Mn1 -2.0(7) . . . . ?
N5 C4 N4 C3 -0.8(4) . . . . ?
C5 C4 N4 C3 176.7(4) . . . . ?
N5 C4 N4 Mn1 -176.8(3) . . . . ?
C5 C4 N4 Mn1 0.8(5) . . . . ?
O1 Mn1 N4 C3 13.0(4) . . . . ?
N3 Mn1 N4 C3 -78.1(4) 14_465 . . . ?
N2 Mn1 N4 C3 161.7(4) 6_554 . . . ?
N6 Mn1 N4 C3 106.5(4) 6_554 . . . ?
N7 Mn1 N4 C3 -170.8(4) . . . . ?
O1 Mn1 N4 C4 -173.7(3) . . . . ?
N3 Mn1 N4 C4 95.1(3) 14_465 . . . ?
N2 Mn1 N4 C4 -25.0(6) 6_554 . . . ?
N6 Mn1 N4 C4 -80.2(3) 6_554 . . . ?
N7 Mn1 N4 C4 2.4(3) . . . . ?
N4 C4 N5 N6 0.2(5) . . . . ?
C5 C4 N5 N6 -177.2(4) . . . . ?
N4 C3 N6 N5 -1.2(5) . . . . ?
C2 C3 N6 N5 176.1(3) . . . . ?
N4 C3 N6 Mn1 -172.1(2) . . . 4_465 ?
C2 C3 N6 Mn1 5.2(4) . . . 4_465 ?
C4 N5 N6 C3 0.6(4) . . . . ?
C4 N5 N6 Mn1 167.7(3) . . . 4_465 ?
C6 C5 N7 C9 2.3(8) . . . . ?
C4 C5 N7 C9 -177.5(4) . . . . ?
C6 C5 N7 Mn1 -172.5(5) . . . . ?
C4 C5 N7 Mn1 7.8(5) . . . . ?
C8 C9 N7 C5 -0.7(8) . . . . ?
C8 C9 N7 Mn1 173.3(5) . . . . ?
O1 Mn1 N7 C5 18.5(9) . . . . ?
N4 Mn1 N7 C5 -5.7(3) . . . . ?
N3 Mn1 N7 C5 -95.7(3) 14_465 . . . ?
N2 Mn1 N7 C5 167.1(3) 6_554 . . . ?
N6 Mn1 N7 C5 93.2(3) 6_554 . . . ?
O1 Mn1 N7 C9 -155.7(7) . . . . ?
N4 Mn1 N7 C9 -179.8(4) . . . . ?
N3 Mn1 N7 C9 90.2(4) 14_465 . . . ?
N2 Mn1 N7 C9 -7.1(4) 6_554 . . . ?
N6 Mn1 N7 C9 -81.0(4) 6_554 . . . ?
O2 C12 N8 C11 -5.3(17) . . . . ?
O2 C12 N8 C10 -179.7(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.086


_database_code_depnum_ccdc_archive 'CCDC 901458'