# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_1



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C15 H18 Cd N O7'

_chemical_formula_weight         436.70



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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_name_H-M_alt        'P 21/c'



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   8.7173(6)

_cell_length_b                   19.4288(17)

_cell_length_c                   9.6558(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 97.170(3)

_cell_angle_gamma                90.00

_cell_volume                     1622.6(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      ?

_cell_measurement_theta_max      ?



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.27

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.788

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             876

_exptl_absorpt_coefficient_mu    1.383

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7064

_exptl_absorpt_correction_T_max  0.7694

_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      173(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  'PHOTON 100 CMOS detector'

_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            2800

_diffrn_reflns_av_R_equivalents  0.0000

_diffrn_reflns_av_sigmaI/netI    0.0704

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       0

_diffrn_reflns_limit_k_max       23

_diffrn_reflns_limit_l_min       0

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.99

_diffrn_reflns_theta_max         25.00

_reflns_number_total             2800

_reflns_number_gt                2211

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'Bruker SHELXTL'

_computing_structure_refinement  'Bruker SHELXTL'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
; 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F², conventional R-factors R are based 

 on F, with F set to zero for negative F². The threshold expression of 

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F² 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/[σ²(Fo²)+(0.0132P)²+8.8805P] where P=(Fo²+2Fc²)/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         2800

_refine_ls_number_parameters     219

_refine_ls_number_restraints     24

_refine_ls_R_factor_all          0.0767

_refine_ls_R_factor_gt           0.0479

_refine_ls_wR_factor_ref         0.0859

_refine_ls_wR_factor_gt          0.0782

_refine_ls_goodness_of_fit_ref   1.001

_refine_ls_restrained_S_all      0.999

_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

























































O7 O 0.0594(11) 0.4206(7) 0.4069(14) 0.0246(17) Uiso 0.621(8) 1 d PD A 1
C12 C 0.1927(16) 0.3339(7) 0.3027(17) 0.030(3) Uiso 0.621(8) 1 d PD A 1
H12A H 0.2833 0.3298 0.2525 0.045 Uiso 0.621(8) 1 calc PR A 1
H12B H 0.1005 0.3181 0.2425 0.045 Uiso 0.621(8) 1 calc PR A 1
H12C H 0.2078 0.3055 0.3872 0.045 Uiso 0.621(8) 1 calc PR A 1
C13 C 0.1720(13) 0.4069(5) 0.3420(13) 0.029(3) Uiso 0.621(8) 1 d PD A 1
N1 N 0.2709(10) 0.4561(4) 0.3177(10) 0.023(2) Uiso 0.621(8) 1 d PD A 1
C14 C 0.2488(16) 0.5268(5) 0.3598(16) 0.028(3) Uiso 0.621(8) 1 d PD A 1
H14A H 0.3332 0.5554 0.3335 0.042 Uiso 0.621(8) 1 calc PR A 1
H14B H 0.2483 0.5288 0.4611 0.042 Uiso 0.621(8) 1 calc PR A 1
H14C H 0.1500 0.5440 0.3130 0.042 Uiso 0.621(8) 1 calc PR A 1
C15 C 0.4127(15) 0.4440(9) 0.256(2) 0.036(3) Uiso 0.621(8) 1 d PD A 1
H15A H 0.4674 0.4876 0.2495 0.055 Uiso 0.621(8) 1 calc PR A 1
H15B H 0.3874 0.4242 0.1629 0.055 Uiso 0.621(8) 1 calc PR A 1
H15C H 0.4787 0.4119 0.3152 0.055 Uiso 0.621(8) 1 calc PR A 1
O7' O 0.0472(18) 0.4313(11) 0.394(2) 0.0246(17) Uiso 0.379(8) 1 d PD A 2
C12' C 0.206(3) 0.5273(9) 0.376(3) 0.030(3) Uiso 0.379(8) 1 d PD A 2
H12D H 0.3064 0.5383 0.3458 0.045 Uiso 0.379(8) 1 calc PR A 2
H12E H 0.2071 0.5398 0.4744 0.045 Uiso 0.379(8) 1 calc PR A 2
H12F H 0.1246 0.5532 0.3193 0.045 Uiso 0.379(8) 1 calc PR A 2
C13' C 0.1755(19) 0.4521(7) 0.358(2) 0.029(3) Uiso 0.379(8) 1 d PD A 2
N1' N 0.2685(16) 0.4092(6) 0.3029(16) 0.023(2) Uiso 0.379(8) 1 d PD A 2
C14' C 0.239(3) 0.3346(8) 0.302(3) 0.028(3) Uiso 0.379(8) 1 d PD A 2
H14D H 0.3183 0.3109 0.2564 0.042 Uiso 0.379(8) 1 calc PR A 2
H14E H 0.1368 0.3252 0.2513 0.042 Uiso 0.379(8) 1 calc PR A 2
H14F H 0.2426 0.3181 0.3984 0.042 Uiso 0.379(8) 1 calc PR A 2
C15' C 0.417(2) 0.4274(15) 0.260(3) 0.036(3) Uiso 0.379(8) 1 d PD A 2
H15D H 0.4624 0.3868 0.2203 0.055 Uiso 0.379(8) 1 calc PR A 2
H15E H 0.4865 0.4436 0.3411 0.055 Uiso 0.379(8) 1 calc PR A 2
H15F H 0.4029 0.4639 0.1895 0.055 Uiso 0.379(8) 1 calc PR A 2
C1 C 1.0413(7) 0.9303(3) 0.5228(7) 0.0112(13) Uani 1 1 d . . .
C2 C 0.9062(7) 0.9556(3) 0.5714(7) 0.0129(14) Uani 1 1 d . . .
C3 C 0.8689(7) 1.0251(3) 0.5473(6) 0.0139(14) Uani 1 1 d . . .
H3 H 0.7785 1.0427 0.5802 0.017 Uiso 1 1 calc R . .
C4 C 1.1029(7) 0.8580(3) 0.5497(7) 0.0135(14) Uani 1 1 d . . .
C5 C 0.5702(7) 0.8438(3) 0.7703(7) 0.0125(14) Uani 1 1 d . . .
C6 C 0.6127(7) 0.8209(3) 0.6430(7) 0.0178(15) Uani 1 1 d . . .
H6 H 0.5639 0.7816 0.5988 0.021 Uiso 1 1 calc R . .
C7 C 0.7246(7) 0.8552(3) 0.5813(7) 0.0178(16) Uani 1 1 d . . .
H7 H 0.7534 0.8386 0.4956 0.021 Uiso 1 1 calc R . .
C8 C 0.7971(7) 0.9143(3) 0.6430(6) 0.0115(14) Uani 1 1 d . . .
C9 C 0.7540(8) 0.9366(3) 0.7691(6) 0.0170(15) Uani 1 1 d . . .
H9 H 0.8005 0.9767 0.8124 0.020 Uiso 1 1 calc R . .
C10 C 0.6427(8) 0.9008(3) 0.8333(7) 0.0173(15) Uani 1 1 d . . .
H10 H 0.6169 0.9159 0.9211 0.021 Uiso 1 1 calc R . .
C11 C 0.4514(7) 0.8045(3) 0.8405(7) 0.0147(15) Uani 1 1 d . . .
Cd1 Cd 1.24810(6) 0.73026(2) 0.55894(6) 0.01423(13) Uani 1 1 d . . .
O1 O 1.1990(5) 0.8366(2) 0.4710(5) 0.0198(11) Uani 1 1 d . . .
O2 O 1.0619(5) 0.8217(2) 0.6449(5) 0.0194(11) Uani 1 1 d . . .
O3 O 0.4355(5) 0.8221(2) 0.9639(5) 0.0197(11) Uani 1 1 d . . .
O4 O 0.3757(5) 0.7577(2) 0.7753(5) 0.0193(11) Uani 1 1 d . . .
O5 O 1.2141(5) 0.6373(2) 0.6930(5) 0.0190(11) Uani 1 1 d D . .
H5A H 1.127(4) 0.622(3) 0.668(7) 0.023 Uiso 1 1 d D . .
H5B H 1.217(7) 0.650(3) 0.774(3) 0.023 Uiso 1 1 d D . .
O6 O 1.0307(6) 0.6876(3) 0.4220(5) 0.0267(13) Uani 1 1 d D . .
H6A H 0.989(8) 0.657(3) 0.459(7) 0.032 Uiso 1 1 d D . .
H6B H 1.049(9) 0.675(4) 0.346(4) 0.032 Uiso 1 1 d 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






























































O7 C13 1.257(12) . ?
C12 C13 1.486(15) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.327(12) . ?
N1 C14 1.454(11) . ?
N1 C15 1.454(11) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O7' C13' 1.275(15) . ?
C12' C13' 1.491(17) . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' N1' 1.321(14) . ?
N1' C15' 1.453(13) . ?
N1' C14' 1.472(14) . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C1 C3 1.398(8) 3_776 ?
C1 C2 1.409(8) . ?
C1 C4 1.515(8) . ?
C2 C3 1.400(8) . ?
C2 C8 1.480(8) . ?
C3 C1 1.398(8) 3_776 ?
C3 H3 0.9500 . ?
C4 O2 1.246(8) . ?
C4 O1 1.269(7) . ?
C5 C10 1.380(9) . ?
C5 C6 1.399(9) . ?
C5 C11 1.514(9) . ?
C6 C7 1.377(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(8) . ?
C9 C10 1.399(9) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O4 1.247(8) . ?
C11 O3 1.264(8) . ?
Cd1 O3 2.218(4) 4_675 ?
Cd1 O1 2.254(4) . ?
Cd1 O5 2.263(5) . ?
Cd1 O4 2.303(5) 1_655 ?
Cd1 O6 2.324(5) . ?
Cd1 O2 2.611(4) . ?
O3 Cd1 2.218(4) 4_476 ?
O4 Cd1 2.303(5) 1_455 ?
O5 H5A 0.82(2) . ?
O5 H5B 0.82(2) . ?
O6 H6A 0.81(2) . ?
O6 H6B 0.81(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










































































































C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C13 N1 120.0(11) . . ?
O7 C13 C12 117.2(11) . . ?
N1 C13 C12 122.7(10) . . ?
C13 N1 C14 121.3(8) . . ?
C13 N1 C15 124.0(10) . . ?
C14 N1 C15 114.6(11) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13' C12' H12D 109.5 . . ?
C13' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C13' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
O7' C13' N1' 120.8(14) . . ?
O7' C13' C12' 115.4(15) . . ?
N1' C13' C12' 123.6(13) . . ?
C13' N1' C15' 125.2(13) . . ?
C13' N1' C14' 120.5(11) . . ?
C15' N1' C14' 113.5(15) . . ?
N1' C14' H14D 109.5 . . ?
N1' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
N1' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
N1' C15' H15D 109.5 . . ?
N1' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
N1' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C3 C1 C2 119.1(5) 3_776 . ?
C3 C1 C4 116.7(5) 3_776 . ?
C2 C1 C4 124.0(5) . . ?
C3 C2 C1 117.8(6) . . ?
C3 C2 C8 116.8(5) . . ?
C1 C2 C8 125.3(6) . . ?
C1 C3 C2 123.0(6) 3_776 . ?
C1 C3 H3 118.5 3_776 . ?
C2 C3 H3 118.5 . . ?
O2 C4 O1 121.8(5) . . ?
O2 C4 C1 121.5(5) . . ?
O1 C4 C1 116.6(6) . . ?
C10 C5 C6 119.1(6) . . ?
C10 C5 C11 120.6(6) . . ?
C6 C5 C11 120.3(6) . . ?
C7 C6 C5 120.4(6) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 118.0(6) . . ?
C9 C8 C2 120.0(6) . . ?
C7 C8 C2 121.7(6) . . ?
C8 C9 C10 120.8(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 120.6(6) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O4 C11 O3 124.1(6) . . ?
O4 C11 C5 119.3(6) . . ?
O3 C11 C5 116.6(6) . . ?
O3 Cd1 O1 112.31(16) 4_675 . ?
O3 Cd1 O5 91.49(17) 4_675 . ?
O1 Cd1 O5 156.17(16) . . ?
O3 Cd1 O4 100.60(17) 4_675 1_655 ?
O1 Cd1 O4 100.21(17) . 1_655 ?
O5 Cd1 O4 75.45(16) . 1_655 ?
O3 Cd1 O6 101.02(18) 4_675 . ?
O1 Cd1 O6 90.57(18) . . ?
O5 Cd1 O6 83.39(18) . . ?
O4 Cd1 O6 149.97(16) 1_655 . ?
O3 Cd1 O2 164.36(15) 4_675 . ?
O1 Cd1 O2 53.13(14) . . ?
O5 Cd1 O2 103.31(15) . . ?
O4 Cd1 O2 78.66(15) 1_655 . ?
O6 Cd1 O2 85.91(18) . . ?
C4 O1 Cd1 100.6(4) . . ?
C4 O2 Cd1 84.5(3) . . ?
C11 O3 Cd1 116.0(4) . 4_476 ?
C11 O4 Cd1 142.4(4) . 1_455 ?
Cd1 O5 H5A 108(5) . . ?
Cd1 O5 H5B 108(5) . . ?
H5A O5 H5B 108(6) . . ?
Cd1 O6 H6A 113(5) . . ?
Cd1 O6 H6B 112(6) . . ?
H6A O6 H6B 110(6) . . ?



_diffrn_measured_fraction_theta_max 0.977

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.977

_refine_diff_density_max         0.891

_refine_diff_density_min         -0.860

_refine_diff_density_rms         0.162
_database_code_depnum_ccdc_archive 'CCDC 1013700'
#######################################################################
#
#                 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_2



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C22 H10 Co2 O10'

_chemical_formula_weight         552.16



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           12

_space_group_name_H-M_alt        'C 2/m'

_space_group_name_Hall           '-C 2y'



loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   18.7009(15)

_cell_length_b                   7.2352(5)

_cell_length_c                   12.5595(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 123.488(2)

_cell_angle_gamma                90.00

_cell_volume                     1417.27(18)

_cell_formula_units_Z            2

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      ?

_cell_measurement_theta_max      ?



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.37

_exptl_crystal_size_mid          0.33

_exptl_crystal_size_min          0.22

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.294

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    1.214

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6635

_exptl_absorpt_correction_T_max  0.7777

_exptl_absorpt_process_details   ?



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      173(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5869

_diffrn_reflns_av_R_equivalents  0.0621

_diffrn_reflns_av_sigmaI/netI    0.0594

_diffrn_reflns_limit_h_min       -23

_diffrn_reflns_limit_h_max       23

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         3.10

_diffrn_reflns_theta_max         26.38

_reflns_number_total             1516

_reflns_number_gt                1022

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'Bruker SHELXTL'

_computing_structure_refinement  'Bruker SHELXTL'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
; 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F², conventional R-factors R are based 

 on F, with F set to zero for negative F². The threshold expression of 

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F² 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/[σ²(Fo²)+(0.1489P)²+9.8438P] where P=(Fo²+2Fc²)/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         1516

_refine_ls_number_parameters     109

_refine_ls_number_restraints     60

_refine_ls_R_factor_all          0.1234

_refine_ls_R_factor_gt           0.0873

_refine_ls_wR_factor_ref         0.2566

_refine_ls_wR_factor_gt          0.2331

_refine_ls_goodness_of_fit_ref   1.094

_refine_ls_restrained_S_all      1.127

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group






















Co1 Co 0.2500 0.2500 0.5000 0.0267(5) Uani 1 2 d S . .
O1 O 0.3080(4) 0.1510(11) 0.4112(5) 0.0564(19) Uani 1 1 d . . .
O2 O 0.6544(4) -0.1500(7) 0.3253(4) 0.0439(15) Uani 1 1 d . . .
C1 C 0.3221(8) 0.0000 0.3818(12) 0.045(3) Uani 1 2 d SU . .
C2 C 0.3639(7) 0.0000 0.3072(10) 0.054(3) Uani 1 2 d SDU . .
C3 C 0.4296(8) -0.1146(13) 0.3358(11) 0.058(5) Uani 0.50 1 d PDU . .
H3A H 0.4536 -0.1931 0.4095 0.070 Uiso 0.50 1 d PR . .
C4 C 0.4658(7) -0.1134(13) 0.2657(10) 0.044(4) Uani 0.50 1 d PDU . .
H4A H 0.5151 -0.1891 0.2921 0.053 Uiso 0.50 1 d PR . .
C5 C 0.4359(6) 0.0000 0.1628(8) 0.039(3) Uani 1 2 d SDU . .
C6 C 0.3684(7) 0.1280(13) 0.1307(10) 0.036(3) Uani 0.50 1 d PDU . .
H6A H 0.3463 0.2082 0.0582 0.043 Uiso 0.50 1 d PR . .
C7 C 0.3321(7) 0.1267(13) 0.2024(11) 0.047(4) Uani 0.50 1 d PDU . .
H7A H 0.2839 0.2046 0.1781 0.056 Uiso 0.50 1 d PR . .
C8 C 0.4703(5) 0.0000 0.0814(8) 0.022(2) Uani 1 2 d S . .
C9 C 0.5561(6) 0.0000 0.1299(7) 0.021(2) Uani 1 2 d S . .
C10 C 0.6271(5) 0.0000 0.2759(7) 0.0188(19) Uani 1 2 d S . .
C11 C 0.5843(6) 0.0000 0.0507(8) 0.029(2) Uani 1 2 d S . .
H11A H 0.6449 0.0000 0.0875 0.035 Uiso 1 2 d SR . .
O1W O 0.3233(5) 0.5000 0.5312(8) 0.047(2) Uani 1 2 d S . .
H1WA H 0.3564 0.5000 0.5048 0.057 Uiso 1 2 d SR . .
H1WB H 0.3189 0.5913 0.5699 0.057 Uiso 0.50 1 d PR . .






_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












































Co1 O2 2.050(4) 5_656 ?
Co1 O2 2.050(4) 3_455 ?
Co1 O1 2.065(6) 7_556 ?
Co1 O1 2.065(6) . ?
Co1 O1W 2.170(4) . ?
Co1 O1W 2.170(4) 7_556 ?
O1 C1 1.228(9) . ?
O2 C10 1.214(6) . ?
O2 Co1 2.050(4) 3_545 ?
C1 O1 1.228(9) 6 ?
C1 C2 1.516(15) . ?
C2 C3 1.356(9) 6 ?
C2 C3 1.356(9) . ?
C2 C7 1.436(9) 6 ?
C2 C7 1.436(9) . ?
C3 C4 1.375(9) . ?
C3 C3 1.658(19) 6 ?
C3 C7 1.664(15) 6 ?
C3 H3A 0.9601 . ?
C4 C5 1.364(9) . ?
C4 C4 1.642(19) 6 ?
C4 C6 1.672(15) 6 ?
C4 H4A 0.9600 . ?
C5 C4 1.364(9) 6 ?
C5 C6 1.432(8) 6 ?
C5 C6 1.432(8) . ?
C5 C8 1.479(13) . ?
C6 C7 1.395(9) . ?
C6 C4 1.672(15) 6 ?
C6 C6 1.852(19) 6 ?
C6 H6A 0.9599 . ?
C7 C3 1.664(15) 6 ?
C7 C7 1.833(19) 6 ?
C7 H7A 0.9599 . ?
C8 C9 1.367(13) . ?
C8 C11 1.387(12) 5_655 ?
C9 C11 1.358(14) . ?
C9 C10 1.561(10) . ?
C10 O2 1.214(6) 6 ?
C11 C8 1.387(12) 5_655 ?
C11 H11A 0.9600 . ?
O1W Co1 2.170(4) 4_556 ?
O1W H1WA 0.8488 . ?
O1W H1WB 0.8500 . ?



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


































































































O2 Co1 O2 180.000(1) 5_656 3_455 ?
O2 Co1 O1 87.2(2) 5_656 7_556 ?
O2 Co1 O1 92.8(2) 3_455 7_556 ?
O2 Co1 O1 92.8(2) 5_656 . ?
O2 Co1 O1 87.2(2) 3_455 . ?
O1 Co1 O1 180.0(2) 7_556 . ?
O2 Co1 O1W 90.6(3) 5_656 . ?
O2 Co1 O1W 89.4(3) 3_455 . ?
O1 Co1 O1W 94.6(3) 7_556 . ?
O1 Co1 O1W 85.4(3) . . ?
O2 Co1 O1W 89.4(3) 5_656 7_556 ?
O2 Co1 O1W 90.6(3) 3_455 7_556 ?
O1 Co1 O1W 85.4(3) 7_556 7_556 ?
O1 Co1 O1W 94.6(3) . 7_556 ?
O1W Co1 O1W 180.0(4) . 7_556 ?
C1 O1 Co1 137.3(7) . . ?
C10 O2 Co1 137.3(5) . 3_545 ?
O1 C1 O1 125.7(11) 6 . ?
O1 C1 C2 117.1(6) 6 . ?
O1 C1 C2 117.1(6) . . ?
C3 C2 C3 75.4(8) 6 . ?
C3 C2 C7 119.3(8) 6 6 ?
C3 C2 C7 73.1(7) . 6 ?
C3 C2 C7 73.1(7) 6 . ?
C3 C2 C7 119.3(8) . . ?
C7 C2 C7 79.3(8) 6 . ?
C3 C2 C1 122.5(7) 6 . ?
C3 C2 C1 122.5(7) . . ?
C7 C2 C1 118.2(7) 6 . ?
C7 C2 C1 118.2(7) . . ?
C2 C3 C4 121.3(9) . . ?
C2 C3 C3 52.3(4) . 6 ?
C4 C3 C3 89.7(4) . 6 ?
C2 C3 C7 55.7(5) . 6 ?
C4 C3 C7 90.5(6) . 6 ?
C3 C3 C7 93.0(4) 6 6 ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.2 . . ?
C3 C3 H3A 126.2 6 . ?
C7 C3 H3A 127.5 6 . ?
C5 C4 C3 121.4(9) . . ?
C5 C4 C4 53.0(4) . 6 ?
C3 C4 C4 90.3(4) . 6 ?
C5 C4 C6 55.2(5) . 6 ?
C3 C4 C6 90.2(6) . 6 ?
C4 C4 C6 93.6(4) 6 6 ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.5 . . ?
C4 C4 H4A 124.8 6 . ?
C6 C4 H4A 128.0 6 . ?
C4 C5 C4 74.0(9) 6 . ?
C4 C5 C6 119.5(8) 6 6 ?
C4 C5 C6 73.4(7) . 6 ?
C4 C5 C6 73.4(7) 6 . ?
C4 C5 C6 119.5(7) . . ?
C6 C5 C6 80.6(9) 6 . ?
C4 C5 C8 123.2(7) 6 . ?
C4 C5 C8 123.2(7) . . ?
C6 C5 C8 117.3(6) 6 . ?
C6 C5 C8 117.3(6) . . ?
C7 C6 C5 118.7(8) . . ?
C7 C6 C4 89.4(6) . 6 ?
C5 C6 C4 51.4(5) . 6 ?
C7 C6 C6 89.6(4) . 6 ?
C5 C6 C6 49.7(4) . 6 ?
C4 C6 C6 86.4(4) 6 6 ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.6 . . ?
C4 C6 H6A 131.2 6 . ?
C6 C6 H6A 127.2 6 . ?
C6 C7 C2 119.6(8) . . ?
C6 C7 C3 89.9(6) . 6 ?
C2 C7 C3 51.2(5) . 6 ?
C6 C7 C7 90.4(4) . 6 ?
C2 C7 C7 50.3(4) . 6 ?
C3 C7 C7 87.0(4) 6 6 ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 120.5 . . ?
C3 C7 H7A 131.8 6 . ?
C7 C7 H7A 125.9 6 . ?
C9 C8 C11 116.2(9) . 5_655 ?
C9 C8 C5 123.0(8) . . ?
C11 C8 C5 120.8(8) 5_655 . ?
C11 C9 C8 120.5(8) . . ?
C11 C9 C10 116.0(8) . . ?
C8 C9 C10 123.5(8) . . ?
O2 C10 O2 126.7(8) 6 . ?
O2 C10 C9 116.5(4) 6 . ?
O2 C10 C9 116.5(4) . . ?
C9 C11 C8 123.3(9) . 5_655 ?
C9 C11 H11A 118.7 . . ?
C8 C11 H11A 118.1 5_655 . ?
Co1 O1W Co1 112.9(3) . 4_556 ?
Co1 O1W H1WA 117.0 . . ?
Co1 O1W H1WA 117.0 4_556 . ?
Co1 O1W H1WB 120.0 . . ?
Co1 O1W H1WB 37.4 4_556 . ?
H1WA O1W H1WB 123.0 . . ?



_diffrn_measured_fraction_theta_max 0.964

_diffrn_reflns_theta_full        26.38

_diffrn_measured_fraction_theta_full 0.964

_refine_diff_density_max         1.416

_refine_diff_density_min         -0.974

_refine_diff_density_rms         0.165

# SQUEEZE RESULTS (APPEND TO CIF)

# Note: Data are Listed for all Voids in the P1 Unit Cell

# i.e. Centre of Gravity, Solvent Accessible Volume,

# Recovered number of Electrons in the Void and

# Details about the Squeezed Material

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 0.000 0.000 -0.007 178 74 ' '
2 0.793 0.000 0.087 5 1 ' '
3 0.207 0.000 0.913 6 1 ' '
4 0.500 0.500 -0.007 178 74 ' '
5 0.293 0.500 0.087 5 1 ' '
6 0.707 0.500 0.913 6 1 ' '

_platon_squeeze_details          
;

;

_database_code_depnum_ccdc_archive 'CCDC 1013701'
#######################################################################
#
#                 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_3



_audit_creation_method           SHELXL-2014

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C30 H28 Mn2 N2 O11'

_chemical_formula_weight         702.42



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 21/n'

_space_group_name_Hall           '-P 2yn'



_shelx_space_group_comment       
;

The symmetry employed for this shelxl refinement is uniquely defined

by the following loop, which should always be used as a source of

symmetry information in preference to the above space-group names.

They are only intended as comments.

;



loop_

_space_group_symop_operation_xyz




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



_cell_length_a                   12.6852(11)

_cell_length_b                   14.7613(15)

_cell_length_c                   16.0030(15)

_cell_angle_alpha                90

_cell_angle_beta                 98.210(3)

_cell_angle_gamma                90

_cell_volume                     2965.9(5)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      ?

_cell_measurement_theta_max      ?



_exptl_crystal_description       block

_exptl_crystal_colour            pink

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.573

_exptl_crystal_F_000             1440

_exptl_transmission_factor_min   ?

_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.368

_exptl_crystal_size_mid          0.325

_exptl_crystal_size_min          0.247

_exptl_absorpt_coefficient_mu    0.917

_shelx_estimated_absorpt_T_min   0.729

_shelx_estimated_absorpt_T_max   0.805

_exptl_absorpt_correction_type   ?

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      173(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            17987

_diffrn_reflns_av_unetI/netI     0.1190

_diffrn_reflns_av_R_equivalents  0.1318

_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -17

_diffrn_reflns_limit_k_max       17

_diffrn_reflns_limit_l_min       -19

_diffrn_reflns_limit_l_max       20

_diffrn_reflns_theta_min         3.045

_diffrn_reflns_theta_max         26.381

_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_max 0.901

_diffrn_measured_fraction_theta_full 0.943

_diffrn_reflns_Laue_measured_fraction_max 0.901

_diffrn_reflns_Laue_measured_fraction_full 0.943

_diffrn_reflns_point_group_measured_fraction_max 0.901

_diffrn_reflns_point_group_measured_fraction_full 0.943

_reflns_number_total             5467

_reflns_number_gt                2809

_reflns_threshold_expression     'I > 2σ(I)'

_reflns_Friedel_coverage         0.000

_reflns_Friedel_fraction_max     .

_reflns_Friedel_fraction_full    .



_reflns_special_details          
;

 Reflections were merged by SHELXL according to the crystal

 class for the calculation of statistics and refinement.

 

 _reflns_Friedel_fraction is defined as the number of unique

 Friedel pairs measured divided by the number that would be

 possible theoretically, ignoring centric projections and

 systematic absences.

;



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'Bruker SHELXTL'

_computing_structure_refinement  'Bruker SHELXTL'

_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)+(0.0400P)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         5467

_refine_ls_number_parameters     417

_refine_ls_number_restraints     18

_refine_ls_R_factor_all          0.1394

_refine_ls_R_factor_gt           0.0503

_refine_ls_wR_factor_ref         0.1136

_refine_ls_wR_factor_gt          0.0886

_refine_ls_goodness_of_fit_ref   0.950

_refine_ls_restrained_S_all      0.952

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_site_symmetry_order

_atom_site_calc_flag

_atom_site_refinement_flags_posn

_atom_site_refinement_flags_adp

_atom_site_refinement_flags_occupancy

_atom_site_disorder_assembly

_atom_site_disorder_group














































































Mn1 Mn 0.52314(4) 0.25119(5) 0.01592(4) 0.01138(18) Uani 1 1 d . . . . .
Mn2 Mn 0.5000 0.5000 0.0000 0.0104(3) Uani 1 2 d S . P . .
Mn3 Mn 0.5000 0.0000 0.0000 0.0122(3) Uani 1 2 d S . P . .
O1 O 1.8402(2) 0.5339(2) 0.4395(2) 0.0246(9) Uani 1 1 d . . . . .
O2 O 1.8350(2) 0.6850(2) 0.4318(2) 0.0244(9) Uani 1 1 d . . . . .
O3 O 1.4173(2) 0.5454(2) 0.1013(2) 0.0189(8) Uani 1 1 d . . . . .
O4 O 1.4033(2) 0.6967(2) 0.0861(2) 0.0174(8) Uani 1 1 d . . . . .
O5 O 1.0450(2) 0.7083(2) 0.3755(2) 0.0212(8) Uani 1 1 d . . . . .
O6 O 1.0827(2) 0.5641(2) 0.4094(2) 0.0244(9) Uani 1 1 d . . . . .
O7 O 0.6392(2) 0.7261(2) 0.0397(2) 0.0257(9) Uani 1 1 d . . . . .
O8 O 0.6375(2) 0.5756(2) 0.0562(2) 0.0234(9) Uani 1 1 d . . . . .
O10 O 0.5717(2) 0.3826(2) 0.07972(17) 0.0147(7) Uani 1 1 d . . . . .
O11 O 0.5444(2) 0.1179(3) -0.2203(2) 0.0298(9) Uani 1 1 d . . . . .
N2 N 0.6683(4) 0.1196(4) -0.3061(3) 0.0438(13) Uani 1 1 d . . . . .
C1 C 1.7944(3) 0.6080(4) 0.4200(3) 0.0159(12) Uani 1 1 d . . . . .
C2 C 1.6793(3) 0.6051(3) 0.3803(3) 0.0159(12) Uani 1 1 d . . . . .
C3 C 1.6057(3) 0.5481(3) 0.4109(3) 0.0180(11) Uani 1 1 d . . . . .
H3A H 1.6285 0.5069 0.4554 0.022 Uiso 1 1 calc R U . . .
C4 C 1.4985(3) 0.5520(3) 0.3759(3) 0.0171(11) Uani 1 1 d . . . . .
H4A H 1.4485 0.5138 0.3976 0.021 Uiso 1 1 calc R U . . .
C5 C 1.4632(3) 0.6111(3) 0.3091(3) 0.0123(10) Uani 1 1 d . . . . .
C6 C 1.5379(3) 0.6663(3) 0.2783(3) 0.0172(11) Uani 1 1 d . . . . .
H6A H 1.5162 0.7062 0.2325 0.021 Uiso 1 1 calc R U . . .
C7 C 1.6442(3) 0.6631(3) 0.3145(3) 0.0159(11) Uani 1 1 d . . . . .
H7A H 1.6940 0.7019 0.2933 0.019 Uiso 1 1 calc R U . . .
C8 C 1.3487(3) 0.6175(3) 0.2737(3) 0.0115(10) Uani 1 1 d . . . . .
C9 C 1.2711(3) 0.6181(3) 0.3282(3) 0.0127(10) Uani 1 1 d . . . . .
H9A H 1.2936 0.6112 0.3871 0.015 Uiso 1 1 calc R U . . .
C10 C 1.1631(3) 0.6282(3) 0.3000(3) 0.0135(10) Uani 1 1 d . . . . .
C11 C 1.1273(3) 0.6386(3) 0.2136(3) 0.0116(11) Uani 1 1 d . . . . .
C12 C 1.2035(3) 0.6369(3) 0.1585(3) 0.0140(11) Uani 1 1 d . . . . .
H12A H 1.1805 0.6432 0.0997 0.017 Uiso 1 1 calc R U . . .
C13 C 1.3122(3) 0.6262(3) 0.1868(3) 0.0107(10) Uani 1 1 d . . . . .
C14 C 1.3848(3) 0.6216(4) 0.1189(3) 0.0122(10) Uani 1 1 d . . . . .
C15 C 1.0894(3) 0.6337(4) 0.3667(3) 0.0137(11) Uani 1 1 d . . . . .
C16 C 1.0119(3) 0.6469(3) 0.1789(3) 0.0119(11) Uani 1 1 d . . . . .
C17 C 0.9366(3) 0.5918(3) 0.2087(3) 0.0169(11) Uani 1 1 d . . . . .
H17A H 0.9578 0.5518 0.2545 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8308(3) 0.5947(3) 0.1722(3) 0.0176(12) Uani 1 1 d . . . . .
H18A H 0.7809 0.5553 0.1925 0.021 Uiso 1 1 calc R U . . .
C19 C 0.7959(3) 0.6540(3) 0.1065(3) 0.0129(11) Uani 1 1 d . . . . .
C20 C 0.8698(3) 0.7133(3) 0.0801(3) 0.0177(11) Uani 1 1 d . . . . .
H20A H 0.8467 0.7576 0.0384 0.021 Uiso 1 1 calc R U . . .
C21 C 0.9764(3) 0.7085(3) 0.1138(3) 0.0169(11) Uani 1 1 d . . . . .
H21A H 1.0262 0.7473 0.0927 0.020 Uiso 1 1 calc R U . . .
C22 C 0.6817(3) 0.6516(3) 0.0644(3) 0.0147(11) Uani 1 1 d . . . . .
C23 C 0.5634(4) 0.3866(4) 0.2358(3) 0.0341(14) Uani 1 1 d . U . . .
H23A H 0.5181 0.4307 0.2018 0.051 Uiso 1 1 d R U . C .
H23B H 0.5706 0.4039 0.2955 0.051 Uiso 1 1 d R U . . .
H23C H 0.5309 0.3263 0.2285 0.051 Uiso 1 1 d R U . . .
C25 C 0.7755(4) 0.3807(5) 0.2629(3) 0.0410(15) Uani 1 1 d . U . . .
H25A H 0.7550 0.4349 0.2921 0.062 Uiso 1 1 calc R U . A 1
H25B H 0.8531 0.3794 0.2651 0.062 Uiso 1 1 calc R U . A 1
H25C H 0.7523 0.3265 0.2906 0.062 Uiso 1 1 calc R U . A 1
C26 C 0.7743(4) 0.3830(4) 0.0903(3) 0.0319(13) Uani 1 1 d . U . . .
H26A H 0.7634 0.3239 0.0624 0.048 Uiso 1 1 calc R U . B 1
H26B H 0.8508 0.3945 0.1048 0.048 Uiso 1 1 calc R U . B 1
H26C H 0.7421 0.4305 0.0522 0.048 Uiso 1 1 calc R U . B 1
C27 C 0.5849(5) 0.1155(5) -0.3786(4) 0.065(2) Uani 1 1 d . . . . .
H27A H 0.6172 0.1159 -0.4307 0.098 Uiso 1 1 calc R U . . .
H27B H 0.5434 0.0599 -0.3759 0.098 Uiso 1 1 calc R U . . .
H27C H 0.5379 0.1682 -0.3780 0.098 Uiso 1 1 calc R U . . .
C28 C 0.7784(5) 0.1278(5) -0.3245(5) 0.073(2) Uani 1 1 d . . . . .
H28A H 0.7784 0.1259 -0.3857 0.110 Uiso 1 1 calc R U . . .
H28B H 0.8088 0.1854 -0.3022 0.110 Uiso 1 1 calc R U . . .
H28C H 0.8212 0.0776 -0.2979 0.110 Uiso 1 1 calc R U . . .
C29 C 0.6412(4) 0.1198(4) -0.2294(4) 0.0326(14) Uani 1 1 d . . . . .
C30 C 0.7245(4) 0.1213(4) -0.1525(4) 0.0380(15) Uani 1 1 d . . . . .
H30A H 0.7954 0.1228 -0.1700 0.057 Uiso 1 1 calc R U . . .
H30B H 0.7147 0.1753 -0.1188 0.057 Uiso 1 1 calc R U . . .
H30C H 0.7176 0.0670 -0.1186 0.057 Uiso 1 1 calc R U . . .
N1A N 0.7226(7) 0.3828(7) 0.1705(5) 0.0240(15) Uani 0.5 1 d . . P C 1
C24A C 0.6178(8) 0.3842(7) 0.1552(6) 0.0142(16) Uani 0.5 1 d . . P C 1
N1B N 0.6693(7) 0.3847(6) 0.2083(5) 0.0240(15) Uani 0.5 1 d . . P C 2
C24B C 0.6663(8) 0.3845(7) 0.1248(7) 0.0142(16) Uani 0.5 1 d . . P C 2
O1W O 0.4803(2) 0.1275(2) -0.07467(17) 0.0154(7) Uani 1 1 d . . . . .
H1WA H 0.4164 0.1322 -0.0988 0.018 Uiso 1 1 d R U . . .
H1WB H 0.5210 0.1268 -0.1125 0.018 Uiso 1 1 d R U . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag






































































































Mn1 O2 2.113(3) 2_745 ?
Mn1 O4 2.136(3) 3_765 ?
Mn1 O5 2.144(3) 2_645 ?
Mn1 O7 2.151(3) 3_665 ?
Mn1 O10 2.237(3) . ?
Mn1 O1W 2.346(3) . ?
Mn2 O8 2.156(3) . ?
Mn2 O8 2.156(3) 3_665 ?
Mn2 O3 2.160(3) 3_765 ?
Mn2 O3 2.160(3) 1_455 ?
Mn2 O10 2.265(3) . ?
Mn2 O10 2.265(3) 3_665 ?
Mn3 O6 2.128(3) 4_565 ?
Mn3 O6 2.128(3) 2_645 ?
Mn3 O1 2.176(3) 2_745 ?
Mn3 O1 2.176(3) 4_465 ?
Mn3 O1W 2.224(3) 3_655 ?
Mn3 O1W 2.225(3) . ?
O1 C1 1.256(6) . ?
O1 Mn3 2.176(3) 2_755 ?
O2 C1 1.251(6) . ?
O2 Mn1 2.113(3) 2_755 ?
O3 C14 1.244(6) . ?
O3 Mn2 2.160(3) 1_655 ?
O4 C14 1.263(6) . ?
O4 Mn1 2.136(3) 3_765 ?
O5 C15 1.255(6) . ?
O5 Mn1 2.144(3) 2_655 ?
O6 C15 1.244(5) . ?
O6 Mn3 2.128(3) 2_655 ?
O7 C22 1.262(5) . ?
O7 Mn1 2.151(3) 3_665 ?
O8 C22 1.253(5) . ?
O10 C24A 1.265(11) . ?
O10 C24B 1.309(11) . ?
O11 C29 1.257(6) . ?
N2 C29 1.321(6) . ?
N2 C27 1.456(7) . ?
N2 C28 1.473(6) . ?
C1 C2 1.508(6) . ?
C2 C7 1.381(6) . ?
C2 C3 1.396(6) . ?
C3 C4 1.397(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.403(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(6) . ?
C5 C8 1.485(5) . ?
C6 C7 1.390(6) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.405(5) . ?
C8 C13 1.408(6) . ?
C9 C10 1.387(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.400(6) . ?
C10 C15 1.519(6) . ?
C11 C12 1.399(6) . ?
C11 C16 1.495(5) . ?
C12 C13 1.397(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.524(5) . ?
C16 C17 1.390(6) . ?
C16 C21 1.408(6) . ?
C17 C18 1.386(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.390(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.391(6) . ?
C19 C22 1.507(6) . ?
C20 C21 1.385(6) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C23 N1B 1.473(9) . ?
C23 C24A 1.549(10) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9799 . ?
C23 H23C 0.9799 . ?
C25 N1B 1.499(10) . ?
C25 N1A 1.535(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N1A 1.521(9) . ?
C26 C24B 1.548(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.503(7) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N1A C24A 1.317(14) . ?
N1B C24B 1.332(13) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?



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



























































































































































































O2 Mn1 O4 91.63(12) 2_745 3_765 ?
O2 Mn1 O5 87.83(13) 2_745 2_645 ?
O4 Mn1 O5 175.20(13) 3_765 2_645 ?
O2 Mn1 O7 161.36(13) 2_745 3_665 ?
O4 Mn1 O7 97.16(12) 3_765 3_665 ?
O5 Mn1 O7 84.74(12) 2_645 3_665 ?
O2 Mn1 O10 93.26(12) 2_745 . ?
O4 Mn1 O10 85.11(11) 3_765 . ?
O5 Mn1 O10 90.16(12) 2_645 . ?
O7 Mn1 O10 103.81(12) 3_665 . ?
O2 Mn1 O1W 89.64(12) 2_745 . ?
O4 Mn1 O1W 84.02(11) 3_765 . ?
O5 Mn1 O1W 100.74(12) 2_645 . ?
O7 Mn1 O1W 75.05(12) 3_665 . ?
O10 Mn1 O1W 168.83(10) . . ?
O8 Mn2 O8 180.0 . 3_665 ?
O8 Mn2 O3 91.31(12) . 3_765 ?
O8 Mn2 O3 88.69(12) 3_665 3_765 ?
O8 Mn2 O3 88.69(12) . 1_455 ?
O8 Mn2 O3 91.31(12) 3_665 1_455 ?
O3 Mn2 O3 180.0 3_765 1_455 ?
O8 Mn2 O10 85.71(12) . . ?
O8 Mn2 O10 94.29(12) 3_665 . ?
O3 Mn2 O10 89.23(11) 3_765 . ?
O3 Mn2 O10 90.77(11) 1_455 . ?
O8 Mn2 O10 94.29(12) . 3_665 ?
O8 Mn2 O10 85.71(12) 3_665 3_665 ?
O3 Mn2 O10 90.77(11) 3_765 3_665 ?
O3 Mn2 O10 89.23(11) 1_455 3_665 ?
O10 Mn2 O10 180.0 . 3_665 ?
O6 Mn3 O6 180.0(2) 4_565 2_645 ?
O6 Mn3 O1 83.53(12) 4_565 2_745 ?
O6 Mn3 O1 96.47(12) 2_645 2_745 ?
O6 Mn3 O1 96.47(12) 4_565 4_465 ?
O6 Mn3 O1 83.53(12) 2_645 4_465 ?
O1 Mn3 O1 180.0(3) 2_745 4_465 ?
O6 Mn3 O1W 87.79(12) 4_565 3_655 ?
O6 Mn3 O1W 92.21(12) 2_645 3_655 ?
O1 Mn3 O1W 85.97(12) 2_745 3_655 ?
O1 Mn3 O1W 94.03(12) 4_465 3_655 ?
O6 Mn3 O1W 92.21(12) 4_565 . ?
O6 Mn3 O1W 87.79(12) 2_645 . ?
O1 Mn3 O1W 94.03(12) 2_745 . ?
O1 Mn3 O1W 85.97(12) 4_465 . ?
O1W Mn3 O1W 180.00(12) 3_655 . ?
C1 O1 Mn3 132.8(3) . 2_755 ?
C1 O2 Mn1 142.1(3) . 2_755 ?
C14 O3 Mn2 131.4(3) . 1_655 ?
C14 O4 Mn1 139.5(3) . 3_765 ?
C15 O5 Mn1 126.2(3) . 2_655 ?
C15 O6 Mn3 145.2(3) . 2_655 ?
C22 O7 Mn1 127.3(3) . 3_665 ?
C22 O8 Mn2 146.2(3) . . ?
C24A O10 Mn1 120.8(5) . . ?
C24B O10 Mn1 116.2(5) . . ?
C24A O10 Mn2 128.1(5) . . ?
C24B O10 Mn2 123.8(5) . . ?
Mn1 O10 Mn2 110.14(12) . . ?
C29 N2 C27 119.0(5) . . ?
C29 N2 C28 124.5(6) . . ?
C27 N2 C28 116.5(5) . . ?
O2 C1 O1 126.0(4) . . ?
O2 C1 C2 116.3(4) . . ?
O1 C1 C2 117.8(4) . . ?
C7 C2 C3 118.8(4) . . ?
C7 C2 C1 119.4(4) . . ?
C3 C2 C1 121.7(4) . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 C8 120.5(4) . . ?
C4 C5 C8 121.2(4) . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C2 C7 C6 121.7(4) . . ?
C2 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C9 C8 C13 116.8(4) . . ?
C9 C8 C5 119.9(4) . . ?
C13 C8 C5 123.2(4) . . ?
C10 C9 C8 123.0(4) . . ?
C10 C9 H9A 118.5 . . ?
C8 C9 H9A 118.5 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 C15 117.0(4) . . ?
C11 C10 C15 122.9(4) . . ?
C12 C11 C10 117.6(4) . . ?
C12 C11 C16 119.7(4) . . ?
C10 C11 C16 122.6(4) . . ?
C13 C12 C11 122.5(4) . . ?
C13 C12 H12A 118.8 . . ?
C11 C12 H12A 118.8 . . ?
C12 C13 C8 120.0(4) . . ?
C12 C13 C14 116.3(4) . . ?
C8 C13 C14 123.6(4) . . ?
O3 C14 O4 127.9(4) . . ?
O3 C14 C13 117.0(4) . . ?
O4 C14 C13 115.1(5) . . ?
O6 C15 O5 126.6(4) . . ?
O6 C15 C10 116.1(5) . . ?
O5 C15 C10 117.2(4) . . ?
C17 C16 C21 118.0(4) . . ?
C17 C16 C11 120.6(4) . . ?
C21 C16 C11 121.4(4) . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 H18A 119.2 . . ?
C19 C18 H18A 119.2 . . ?
C18 C19 C20 118.0(4) . . ?
C18 C19 C22 120.3(4) . . ?
C20 C19 C22 121.6(4) . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?
O8 C22 O7 125.6(4) . . ?
O8 C22 C19 117.0(4) . . ?
O7 C22 C19 117.4(4) . . ?
N1B C23 H23A 109.5 . . ?
C24A C23 H23A 81.2 . . ?
N1B C23 H23B 109.5 . . ?
C24A C23 H23B 145.8 . . ?
H23A C23 H23B 109.5 . . ?
N1B C23 H23C 109.4 . . ?
C24A C23 H23C 96.3 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1A C25 H25A 109.5 . . ?
N1A C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1A C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1A C26 H26A 109.5 . . ?
N1A C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N1A C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O11 C29 N2 119.7(5) . . ?
O11 C29 C30 119.3(5) . . ?
N2 C29 C30 120.9(5) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24A N1A C26 112.9(8) . . ?
C24A N1A C25 118.0(7) . . ?
C26 N1A C25 129.1(7) . . ?
O10 C24A N1A 119.6(8) . . ?
O10 C24A C23 126.6(8) . . ?
N1A C24A C23 113.8(8) . . ?
C24B N1B C23 113.8(8) . . ?
C24B N1B C25 118.7(8) . . ?
C23 N1B C25 127.5(7) . . ?
O10 C24B N1B 116.4(8) . . ?
O10 C24B C26 126.3(8) . . ?
N1B C24B C26 117.2(9) . . ?
Mn3 O1W Mn1 109.16(11) . . ?
Mn3 O1W H1WA 109.9 . . ?
Mn1 O1W H1WA 109.8 . . ?
Mn3 O1W H1WB 109.9 . . ?
Mn1 O1W H1WB 109.8 . . ?
H1WA O1W H1WB 108.3 . . ?



_refine_diff_density_max         0.546

_refine_diff_density_min         -0.442

_refine_diff_density_rms         0.095



_shelxl_version_number           2014-3




_database_code_depnum_ccdc_archive 'CCDC 1013702'
