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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0606-ypf-055
_database_code_depnum_ccdc_archive 'CCDC 1033515'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2014-11-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H16 Cl8 Co5 N16, 2(C6 H15 N)'
_chemical_formula_sum            'C40 H46 Cl8 Co5 N18'
_chemical_formula_weight         1357.20
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.5936(6)
_cell_length_b                   11.9201(7)
_cell_length_c                   12.1223(6)
_cell_angle_alpha                63.593(5)
_cell_angle_beta                 88.025(4)
_cell_angle_gamma                67.331(5)
_cell_volume                     1365.40(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    299.4(7)
_cell_measurement_theta_max      29.1725
_cell_measurement_theta_min      2.9207
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            glaucous
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             683
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16802
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      299.4(7)
_diffrn_detector_area_resol_mean 16.1623
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   21.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6281  -99.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   17.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6281  -99.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   20.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6281  -99.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   36.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906  -57.0000  -90.0000 168

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   38.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906  -57.0000   30.0000 174

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00   35.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906  -57.0000  150.0000 164

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   88.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906   57.0000 -180.0000 174

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   83.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906   45.0000  -42.0000 168

#__ type_ start__ end____ width___ exp.time_
  9 omega    1.00   88.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6906   57.0000   60.0000 174
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0333782000
_diffrn_orient_matrix_UB_12      -0.0708338000
_diffrn_orient_matrix_UB_13      0.0172613000
_diffrn_orient_matrix_UB_21      -0.0485220000
_diffrn_orient_matrix_UB_22      -0.0139605000
_diffrn_orient_matrix_UB_23      0.0332027000
_diffrn_orient_matrix_UB_31      -0.0324306000
_diffrn_orient_matrix_UB_32      0.0105209000
_diffrn_orient_matrix_UB_33      -0.0546656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3667
_reflns_number_total             5578
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.8577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1433
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Co3 Co 0.79802(7) 0.18642(9) 0.83959(7) 0.0311(2) Uani 1 1 d . . .
Co1 Co 0.75840(7) 0.45878(9) 0.30276(7) 0.0304(2) Uani 1 1 d . . .
Co2 Co 0.5000 0.5000 0.5000 0.0253(3) Uani 1 2 d S . .
Cl1 Cl 0.7580(2) 0.5951(2) 0.10559(15) 0.0718(6) Uani 1 1 d . . .
Cl2 Cl 0.92818(16) 0.2609(2) 0.40573(18) 0.0621(5) Uani 1 1 d . . .
Cl3 Cl 0.63834(16) 0.25759(18) 0.69018(14) 0.0481(4) Uani 1 1 d . . .
Cl4 Cl 0.86950(17) -0.04090(18) 0.94548(17) 0.0567(5) Uani 1 1 d . . .
N1 N 0.7253(4) 0.2628(5) -0.0411(4) 0.0344(12) Uani 1 1 d . . .
N2 N 0.4700(4) 0.3223(5) 0.2935(4) 0.0316(11) Uani 1 1 d . . .
N3 N 0.6106(4) 0.4058(5) 0.3069(4) 0.0271(11) Uani 1 1 d . . .
N4 N 0.5321(4) 0.4167(5) 0.3899(4) 0.0259(11) Uani 1 1 d . . .
N5 N 0.3613(4) 0.4430(5) 0.5226(4) 0.0275(11) Uani 1 1 d . . .
N6 N 0.2727(4) 0.4366(5) 0.5972(4) 0.0286(11) Uani 1 1 d . . .
N7 N 0.2742(4) 0.3158(5) 0.4972(4) 0.0322(12) Uani 1 1 d . . .
N8 N -0.0674(4) 0.2483(5) 0.7598(4) 0.0334(12) Uani 1 1 d . . .
N9 N 0.7021(8) 0.9249(8) 0.7388(7) 0.075(2) Uani 1 1 d . . .
C1 C 0.8005(6) 0.2514(7) 0.0479(6) 0.0453(18) Uani 1 1 d . . .
H1 H 0.8869 0.2237 0.0452 0.054 Uiso 1 1 calc R . .
C2 C 0.7545(5) 0.2794(7) 0.1441(6) 0.0414(16) Uani 1 1 d . . .
H2 H 0.8094 0.2716 0.2039 0.050 Uiso 1 1 calc R . .
C3 C 0.6276(5) 0.3187(6) 0.1510(5) 0.0287(13) Uani 1 1 d . . .
C4 C 0.5500(5) 0.3304(6) 0.0586(5) 0.0323(14) Uani 1 1 d . . .
H4 H 0.4633 0.3582 0.0591 0.039 Uiso 1 1 calc R . .
C5 C 0.6023(5) 0.3006(6) -0.0338(5) 0.0334(14) Uani 1 1 d . . .
H5 H 0.5492 0.3072 -0.0942 0.040 Uiso 1 1 calc R . .
C6 C 0.5702(5) 0.3482(6) 0.2510(5) 0.0268(13) Uani 1 1 d . . .
C7 C 0.4520(5) 0.3648(6) 0.3803(5) 0.0266(13) Uani 1 1 d . . .
C8 C 0.3590(5) 0.3705(6) 0.4641(5) 0.0268(13) Uani 1 1 d . . .
C9 C 0.2215(5) 0.3607(6) 0.5791(5) 0.0294(13) Uani 1 1 d . . .
C10 C 0.1208(5) 0.3256(6) 0.6431(5) 0.0294(14) Uani 1 1 d . . .
C11 C 0.1177(6) 0.2021(7) 0.6658(6) 0.0495(19) Uani 1 1 d . . .
H11 H 0.1789 0.1425 0.6424 0.059 Uiso 1 1 calc R . .
C12 C 0.0220(7) 0.1689(7) 0.7238(6) 0.0521(19) Uani 1 1 d . . .
H12 H 0.0208 0.0860 0.7381 0.063 Uiso 1 1 calc R . .
C13 C -0.0637(5) 0.3668(7) 0.7377(6) 0.0401(16) Uani 1 1 d . . .
H13 H -0.1262 0.4248 0.7616 0.048 Uiso 1 1 calc R . .
C14 C 0.0281(6) 0.4068(7) 0.6812(6) 0.0454(17) Uani 1 1 d . . .
H14 H 0.0273 0.4900 0.6686 0.054 Uiso 1 1 calc R . .
C15 C 0.6597(13) 0.9769(13) 0.6037(12) 0.157(5) Uani 1 1 d U . .
H15A H 0.6485 0.9059 0.5924 0.189 Uiso 1 1 calc R . .
H15B H 0.5786 1.0559 0.5756 0.189 Uiso 1 1 calc R . .
C16 C 0.7510(11) 1.0161(11) 0.5292(11) 0.145(5) Uani 1 1 d U . .
H16A H 0.7080 1.1057 0.4592 0.218 Uiso 1 1 calc R . .
H16B H 0.7937 0.9505 0.4997 0.218 Uiso 1 1 calc R . .
H16C H 0.8119 1.0181 0.5792 0.218 Uiso 1 1 calc R . .
C17 C 0.8216(11) 0.7923(12) 0.7958(10) 0.117(4) Uani 1 1 d U . .
H17A H 0.8907 0.8133 0.7582 0.141 Uiso 1 1 calc R . .
H17B H 0.8391 0.7653 0.8838 0.141 Uiso 1 1 calc R . .
C18 C 0.8267(11) 0.6811(11) 0.7878(10) 0.119(4) Uani 1 1 d U . .
H18A H 0.8310 0.6964 0.7033 0.179 Uiso 1 1 calc R . .
H18B H 0.7521 0.6660 0.8123 0.179 Uiso 1 1 calc R . .
H18C H 0.9005 0.6018 0.8422 0.179 Uiso 1 1 calc R . .
C19 C 0.5943(13) 0.9054(14) 0.8068(13) 0.155(5) Uani 1 1 d U . .
H19A H 0.5625 0.8586 0.7760 0.186 Uiso 1 1 calc R . .
H19B H 0.6309 0.8421 0.8940 0.186 Uiso 1 1 calc R . .
C20 C 0.4920(12) 1.0127(12) 0.8043(13) 0.161(6) Uani 1 1 d U . .
H20A H 0.4546 1.0798 0.7191 0.242 Uiso 1 1 calc R . .
H20B H 0.5180 1.0539 0.8453 0.242 Uiso 1 1 calc R . .
H20C H 0.4309 0.9803 0.8465 0.242 Uiso 1 1 calc R . .


_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
Co3 Cl3 2.2541(17) . ?
Co3 Cl4 2.219(2) . ?
Co3 N1 2.031(4) 1_556 ?
Co3 N8 2.015(4) 1_655 ?
Co1 Cl1 2.2122(19) . ?
Co1 Cl2 2.229(2) . ?
Co1 N3 2.034(4) . ?
Co1 N6 2.030(4) 2_666 ?
Co2 Cl3 2.6446(17) . ?
Co2 Cl3 2.6446(17) 2_666 ?
Co2 N4 1.941(4) . ?
Co2 N4 1.941(4) 2_666 ?
Co2 N5 1.941(4) 2_666 ?
Co2 N5 1.941(4) . ?
N1 Co3 2.031(4) 1_554 ?
N1 C1 1.337(7) . ?
N1 C5 1.332(7) . ?
N2 C6 1.343(7) . ?
N2 C7 1.336(6) . ?
N3 N4 1.348(5) . ?
N3 C6 1.353(6) . ?
N4 C7 1.331(6) . ?
N5 N6 1.347(5) . ?
N5 C8 1.347(6) . ?
N6 Co1 2.030(4) 2_666 ?
N6 C9 1.348(7) . ?
N7 C8 1.335(6) . ?
N7 C9 1.350(6) . ?
N8 Co3 2.015(4) 1_455 ?
N8 C12 1.320(7) . ?
N8 C13 1.333(7) . ?
N9 C15 1.491(13) . ?
N9 C17 1.517(12) . ?
N9 C19 1.510(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(7) . ?
C3 C4 1.384(7) . ?
C3 C6 1.477(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(7) . ?
C5 H5 0.9300 . ?
C7 C8 1.460(7) . ?
C9 C10 1.472(7) . ?
C10 C11 1.387(8) . ?
C10 C14 1.366(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.372(8) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.447(14) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.350(12) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.357(14) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
Cl4 Co3 Cl3 106.49(7) . . ?
N1 Co3 Cl3 108.31(14) 1_556 . ?
N1 Co3 Cl4 107.51(15) 1_556 . ?
N8 Co3 Cl3 109.58(14) 1_655 . ?
N8 Co3 Cl4 112.52(16) 1_655 . ?
N8 Co3 N1 112.18(19) 1_655 1_556 ?
Cl1 Co1 Cl2 118.35(9) . . ?
N3 Co1 Cl1 107.61(13) . . ?
N3 Co1 Cl2 105.56(14) . . ?
N6 Co1 Cl1 109.75(14) 2_666 . ?
N6 Co1 Cl2 107.69(14) 2_666 . ?
N6 Co1 N3 107.33(16) 2_666 . ?
Cl3 Co2 Cl3 180.000(1) . 2_666 ?
N4 Co2 Cl3 89.85(14) . . ?
N4 Co2 Cl3 90.15(14) 2_666 . ?
N4 Co2 Cl3 90.15(14) . 2_666 ?
N4 Co2 Cl3 89.85(14) 2_666 2_666 ?
N4 Co2 N4 180.000(1) 2_666 . ?
N5 Co2 Cl3 87.48(14) . . ?
N5 Co2 Cl3 92.52(14) . 2_666 ?
N5 Co2 Cl3 87.48(14) 2_666 2_666 ?
N5 Co2 Cl3 92.52(14) 2_666 . ?
N5 Co2 N4 81.02(17) 2_666 2_666 ?
N5 Co2 N4 98.98(17) . 2_666 ?
N5 Co2 N4 98.98(17) 2_666 . ?
N5 Co2 N4 81.02(17) . . ?
N5 Co2 N5 180.0 2_666 . ?
Co3 Cl3 Co2 132.92(7) . . ?
C1 N1 Co3 121.4(4) . 1_554 ?
C5 N1 Co3 119.8(4) . 1_554 ?
C5 N1 C1 117.5(5) . . ?
C7 N2 C6 101.3(4) . . ?
N4 N3 Co1 118.8(3) . . ?
N4 N3 C6 104.9(4) . . ?
C6 N3 Co1 136.1(3) . . ?
N3 N4 Co2 136.9(3) . . ?
C7 N4 Co2 116.4(3) . . ?
C7 N4 N3 106.4(4) . . ?
N6 N5 Co2 137.4(3) . . ?
C8 N5 Co2 115.5(3) . . ?
C8 N5 N6 106.1(4) . . ?
N5 N6 Co1 118.3(3) . 2_666 ?
N5 N6 C9 105.6(4) . . ?
C9 N6 Co1 136.1(4) . 2_666 ?
C8 N7 C9 101.7(4) . . ?
C12 N8 Co3 118.6(4) . 1_455 ?
C12 N8 C13 117.0(5) . . ?
C13 N8 Co3 124.4(4) . 1_455 ?
C15 N9 C17 113.8(8) . . ?
C15 N9 C19 107.6(9) . . ?
C19 N9 C17 110.4(8) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(5) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.6(5) . . ?
C2 C3 C6 123.7(5) . . ?
C4 C3 C6 118.6(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 123.3(5) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N2 C6 N3 113.5(4) . . ?
N2 C6 C3 122.4(5) . . ?
N3 C6 C3 124.1(5) . . ?
N2 C7 C8 132.9(5) . . ?
N4 C7 N2 113.9(4) . . ?
N4 C7 C8 113.2(4) . . ?
N5 C8 C7 113.3(5) . . ?
N7 C8 N5 113.4(4) . . ?
N7 C8 C7 133.3(5) . . ?
N6 C9 N7 113.2(5) . . ?
N6 C9 C10 124.6(5) . . ?
N7 C9 C10 122.2(5) . . ?
C11 C10 C9 118.3(5) . . ?
C14 C10 C9 124.7(5) . . ?
C14 C10 C11 117.0(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.5 . . ?
N8 C12 C11 123.7(6) . . ?
N8 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
N8 C13 H13 118.6 . . ?
N8 C13 C14 122.9(6) . . ?
C14 C13 H13 118.6 . . ?
C10 C14 C13 120.5(6) . . ?
C10 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N9 C15 H15A 109.4 . . ?
N9 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 N9 111.2(11) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N9 C17 H17A 107.3 . . ?
N9 C17 H17B 107.3 . . ?
H17A C17 H17B 106.9 . . ?
C18 C17 N9 120.0(10) . . ?
C18 C17 H17A 107.3 . . ?
C18 C17 H17B 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N9 C19 H19A 106.8 . . ?
N9 C19 H19B 106.8 . . ?
H19A C19 H19B 106.6 . . ?
C20 C19 N9 122.2(12) . . ?
C20 C19 H19A 106.8 . . ?
C20 C19 H19B 106.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
Co3 N1 C1 C2 -167.9(5) 1_554 . . . ?
Co3 N1 C5 C4 168.4(5) 1_554 . . . ?
Co3 N8 C12 C11 178.7(5) 1_455 . . . ?
Co3 N8 C13 C14 -178.8(5) 1_455 . . . ?
Co1 N3 N4 Co2 12.4(7) . . . . ?
Co1 N3 N4 C7 -174.7(4) . . . . ?
Co1 N3 C6 N2 174.4(4) . . . . ?
Co1 N3 C6 C3 -6.9(9) . . . . ?
Co1 N6 C9 N7 177.5(4) 2_666 . . . ?
Co1 N6 C9 C10 -4.0(9) 2_666 . . . ?
Co2 N4 C7 N2 173.1(4) . . . . ?
Co2 N4 C7 C8 -4.8(6) . . . . ?
Co2 N5 N6 Co1 14.6(7) . . . 2_666 ?
Co2 N5 N6 C9 -168.1(4) . . . . ?
Co2 N5 C8 N7 170.4(4) . . . . ?
Co2 N5 C8 C7 -8.0(6) . . . . ?
Cl1 Co1 N3 N4 -131.8(4) . . . . ?
Cl1 Co1 N3 C6 54.7(6) . . . . ?
Cl2 Co1 N3 N4 100.9(4) . . . . ?
Cl2 Co1 N3 C6 -72.6(5) . . . . ?
Cl3 Co2 Cl3 Co3 178(100) 2_666 . . . ?
Cl3 Co2 N4 N3 -99.7(5) . . . . ?
Cl3 Co2 N4 N3 80.3(5) 2_666 . . . ?
Cl3 Co2 N4 C7 87.9(4) . . . . ?
Cl3 Co2 N4 C7 -92.1(4) 2_666 . . . ?
Cl3 Co2 N5 N6 81.2(5) . . . . ?
Cl3 Co2 N5 N6 -98.8(5) 2_666 . . . ?
Cl3 Co2 N5 C8 94.1(4) 2_666 . . . ?
Cl3 Co2 N5 C8 -85.9(4) . . . . ?
Cl4 Co3 Cl3 Co2 -173.50(9) . . . . ?
N1 Co3 Cl3 Co2 71.12(18) 1_556 . . . ?
N1 C1 C2 C3 0.9(10) . . . . ?
N2 C7 C8 N5 -169.1(6) . . . . ?
N2 C7 C8 N7 12.9(11) . . . . ?
N3 N4 C7 N2 -1.5(7) . . . . ?
N3 N4 C7 C8 -179.4(4) . . . . ?
N4 Co2 Cl3 Co3 130.55(15) . . . . ?
N4 Co2 Cl3 Co3 -49.45(15) 2_666 . . . ?
N4 Co2 N4 N3 56(100) 2_666 . . . ?
N4 Co2 N4 C7 -117(100) 2_666 . . . ?
N4 Co2 N5 N6 -8.5(6) 2_666 . . . ?
N4 Co2 N5 N6 171.5(6) . . . . ?
N4 Co2 N5 C8 -175.6(4) 2_666 . . . ?
N4 Co2 N5 C8 4.4(4) . . . . ?
N4 N3 C6 N2 0.3(6) . . . . ?
N4 N3 C6 C3 179.0(5) . . . . ?
N4 C7 C8 N5 8.3(7) . . . . ?
N4 C7 C8 N7 -169.7(6) . . . . ?
N5 Co2 Cl3 Co3 -148.43(15) . . . . ?
N5 Co2 Cl3 Co3 31.57(15) 2_666 . . . ?
N5 Co2 N4 N3 -7.1(5) 2_666 . . . ?
N5 Co2 N4 N3 172.9(5) . . . . ?
N5 Co2 N4 C7 -179.5(4) 2_666 . . . ?
N5 Co2 N4 C7 0.5(4) . . . . ?
N5 Co2 N5 N6 -125(100) 2_666 . . . ?
N5 Co2 N5 C8 68(100) 2_666 . . . ?
N5 N6 C9 N7 0.9(6) . . . . ?
N5 N6 C9 C10 179.3(5) . . . . ?
N6 Co1 N3 N4 -13.7(4) 2_666 . . . ?
N6 Co1 N3 C6 172.7(5) 2_666 . . . ?
N6 N5 C8 N7 -0.6(6) . . . . ?
N6 N5 C8 C7 -179.0(4) . . . . ?
N6 C9 C10 C11 -149.3(6) . . . . ?
N6 C9 C10 C14 31.4(9) . . . . ?
N7 C9 C10 C11 29.0(8) . . . . ?
N7 C9 C10 C14 -150.3(6) . . . . ?
N8 Co3 Cl3 Co2 -51.55(19) 1_655 . . . ?
N8 C13 C14 C10 0.8(10) . . . . ?
C1 N1 C5 C4 1.2(9) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C1 C2 C3 C6 178.9(6) . . . . ?
C2 C3 C4 C5 1.1(9) . . . . ?
C2 C3 C6 N2 -147.3(6) . . . . ?
C2 C3 C6 N3 34.0(9) . . . . ?
C3 C4 C5 N1 -1.3(9) . . . . ?
C4 C3 C6 N2 32.4(8) . . . . ?
C4 C3 C6 N3 -146.2(6) . . . . ?
C5 N1 C1 C2 -1.0(10) . . . . ?
C6 N2 C7 N4 1.5(6) . . . . ?
C6 N2 C7 C8 178.9(6) . . . . ?
C6 N3 N4 Co2 -172.2(4) . . . . ?
C6 N3 N4 C7 0.7(6) . . . . ?
C6 C3 C4 C5 -178.7(5) . . . . ?
C7 N2 C6 N3 -1.1(6) . . . . ?
C7 N2 C6 C3 -179.8(5) . . . . ?
C8 N5 N6 Co1 -177.5(3) . . . 2_666 ?
C8 N5 N6 C9 -0.2(6) . . . . ?
C8 N7 C9 N6 -1.1(6) . . . . ?
C8 N7 C9 C10 -179.6(5) . . . . ?
C9 N7 C8 N5 1.0(6) . . . . ?
C9 N7 C8 C7 179.0(6) . . . . ?
C9 C10 C11 C12 -178.8(6) . . . . ?
C9 C10 C14 C13 178.5(5) . . . . ?
C10 C11 C12 N8 -0.3(11) . . . . ?
C11 C10 C14 C13 -0.8(9) . . . . ?
C12 N8 C13 C14 -0.5(9) . . . . ?
C13 N8 C12 C11 0.3(10) . . . . ?
C14 C10 C11 C12 0.5(9) . . . . ?
C15 N9 C17 C18 -55.0(14) . . . . ?
C15 N9 C19 C20 -77.4(16) . . . . ?
C17 N9 C15 C16 -65.1(13) . . . . ?
C17 N9 C19 C20 157.9(14) . . . . ?
C19 N9 C15 C16 172.2(10) . . . . ?
C19 N9 C17 C18 66.1(12) . . . . ?

####################################################################### 
# 
# 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_0719-ypf-081a
_database_code_depnum_ccdc_archive 'CCDC 1033516'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2014-11-09
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C30 H16 Co3 N8 O8, 0.5(C H4 O)'
_chemical_formula_sum            'C30.50 H18 Co3 N8 O8.50'
_chemical_formula_weight         809.32
_chemical_melting_point          ?
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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.2529(12)
_cell_length_b                   10.6355(11)
_cell_length_c                   11.0493(13)
_cell_angle_alpha                63.622(11)
_cell_angle_beta                 86.489(10)
_cell_angle_gamma                74.907(10)
_cell_volume                     938.68(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3513
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8018
_cell_measurement_theta_min      2.9736
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6688
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -84.00    4.00   1.0000    8.4300
omega____ theta____ kappa____ phi______ frames
    -      -17.4897  -57.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   55.00   1.0000    8.4300
omega____ theta____ kappa____ phi______ frames
    -      -17.4897   19.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   10.00   1.0000    8.4300
omega____ theta____ kappa____ phi______ frames
    -      -17.4897  -77.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   47.00   1.0000    8.4300
omega____ theta____ kappa____ phi______ frames
    -      -17.4897   57.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00   57.00   1.0000    8.4300
omega____ theta____ kappa____ phi______ frames
    -       18.7397  -99.0000  -90.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0450811000
_diffrn_orient_matrix_UB_12      0.0570853000
_diffrn_orient_matrix_UB_13      0.0131867000
_diffrn_orient_matrix_UB_21      -0.0590496000
_diffrn_orient_matrix_UB_22      0.0081742000
_diffrn_orient_matrix_UB_23      -0.0430882000
_diffrn_orient_matrix_UB_31      -0.0284531000
_diffrn_orient_matrix_UB_32      -0.0511901000
_diffrn_orient_matrix_UB_33      0.0558955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3302
_reflns_number_total             3840
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0913P)²+3.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.1933
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5000 0.5000 0.5000 0.0147(2) Uani 1 2 d S . .
Co2 Co 0.22196(7) 0.27529(7) 0.48166(6) 0.0175(2) Uani 1 1 d . . .
O1 O 0.4734(4) 0.3090(4) 0.6677(4) 0.0279(8) Uani 1 1 d . . .
O2 O 0.3242(5) 0.1765(4) 0.6608(4) 0.0379(10) Uani 1 1 d . . .
O3 O 0.4904(4) 0.4171(5) 0.3592(4) 0.0316(9) Uani 1 1 d . . .
O4 O 0.3163(5) 0.3339(5) 0.3089(4) 0.0361(10) Uani 1 1 d . . .
O5 O -0.058(5) 0.259(5) 0.881(4) 0.130(14) Uani 0.25 1 d P . .
H5 H -0.0930 0.2246 0.9555 0.196 Uiso 0.25 1 calc PR . .
N1 N -0.0221(4) 0.3385(4) 0.4905(4) 0.0208(9) Uani 1 1 d . . .
N2 N -0.1945(4) 0.5125(5) 0.5213(4) 0.0208(9) Uani 1 1 d . . .
N3 N -0.2656(4) 0.4141(4) 0.5213(4) 0.0183(8) Uani 1 1 d . . .
N4 N -0.2251(5) -0.0714(5) 0.5084(5) 0.0237(9) Uani 1 1 d . . .
C1 C 0.4166(6) 0.2056(6) 0.7180(5) 0.0248(11) Uani 1 1 d . . .
C2 C 0.4608(6) 0.0985(6) 0.8648(5) 0.0266(11) Uani 1 1 d . . .
C3 C 0.5565(8) 0.1209(7) 0.9404(6) 0.0402(15) Uani 1 1 d . . .
H3 H 0.5940 0.2024 0.9008 0.048 Uiso 1 1 calc R . .
C4 C 0.5969(8) 0.0221(7) 1.0753(6) 0.0409(16) Uani 1 1 d . . .
H4 H 0.6624 0.0369 1.1252 0.049 Uiso 1 1 calc R . .
C5 C 0.044(6) 0.320(6) 0.889(4) 0.097(16) Uani 0.25 1 d P . .
H5A H 0.0106 0.3721 0.9418 0.146 Uiso 0.25 1 calc PR . .
H5B H 0.0613 0.3869 0.7991 0.146 Uiso 0.25 1 calc PR . .
H5C H 0.1355 0.2470 0.9301 0.146 Uiso 0.25 1 calc PR . .
C6 C 0.4212(6) 0.3974(6) 0.2799(5) 0.0254(11) Uani 1 1 d . . .
C7 C 0.4629(6) 0.4492(6) 0.1343(5) 0.0275(11) Uani 1 1 d . . .
C8 C 0.5759(8) 0.5187(8) 0.0933(6) 0.0388(15) Uani 1 1 d . . .
H8 H 0.6270 0.5318 0.1549 0.047 Uiso 1 1 calc R . .
C9 C 0.6134(8) 0.5694(8) -0.0417(6) 0.0415(16) Uani 1 1 d . . .
H9 H 0.6902 0.6159 -0.0697 0.050 Uiso 1 1 calc R . .
C10 C -0.0546(5) 0.4632(5) 0.5018(5) 0.0209(10) Uani 1 1 d . . .
C11 C -0.1608(5) 0.3124(5) 0.5024(5) 0.0184(9) Uani 1 1 d . . .
C12 C -0.1897(5) 0.1828(5) 0.5017(6) 0.0226(10) Uani 1 1 d . . .
C13 C -0.1524(7) 0.1504(6) 0.3925(6) 0.0294(12) Uani 1 1 d . . .
H13 H -0.1148 0.2134 0.3162 0.035 Uiso 1 1 calc R . .
C14 C -0.1725(7) 0.0230(6) 0.4004(5) 0.0297(12) Uani 1 1 d . . .
H14 H -0.1485 0.0018 0.3273 0.036 Uiso 1 1 calc R . .
C15 C -0.2623(7) -0.0374(7) 0.6112(6) 0.0352(14) Uani 1 1 d . . .
H15 H -0.3000 -0.1016 0.6866 0.042 Uiso 1 1 calc R . .
C16 C -0.2470(7) 0.0888(7) 0.6103(6) 0.0346(13) Uani 1 1 d . . .
H16 H -0.2755 0.1093 0.6831 0.041 Uiso 1 1 calc R . .


_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 O1 2.116(3) . ?
Co1 O1 2.116(3) 2_666 ?
Co1 O3 2.118(4) 2_666 ?
Co1 O3 2.118(4) . ?
Co1 N3 2.106(4) 2_566 ?
Co1 N3 2.106(4) 1_655 ?
Co2 O2 1.945(4) . ?
Co2 O4 1.953(4) . ?
Co2 N1 2.191(4) . ?
Co2 N2 2.191(4) 2_566 ?
Co2 N4 2.114(4) 2_556 ?
O1 C1 1.232(6) . ?
O2 C1 1.267(6) . ?
O3 C6 1.234(6) . ?
O4 C6 1.269(6) . ?
O5 H5 0.8200 . ?
O5 C5 1.30(5) . ?
N1 C10 1.342(6) . ?
N1 C11 1.369(6) . ?
N2 Co2 2.191(4) 2_566 ?
N2 N3 1.373(5) . ?
N2 C10 1.308(6) . ?
N3 Co1 2.106(4) 1_455 ?
N3 C11 1.336(6) . ?
N4 Co2 2.114(4) 2_556 ?
N4 C14 1.337(7) . ?
N4 C15 1.339(7) . ?
C1 C2 1.513(7) . ?
C2 C3 1.384(8) . ?
C2 C4 1.388(8) 2_657 ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C4 C2 1.388(8) 2_657 ?
C4 H4 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.512(7) . ?
C7 C8 1.375(8) . ?
C7 C9 1.388(8) 2_665 ?
C8 H8 0.9300 . ?
C8 C9 1.399(8) . ?
C9 C7 1.388(8) 2_665 ?
C9 H9 0.9300 . ?
C10 C10 1.420(9) 2_566 ?
C11 C12 1.473(6) . ?
C12 C13 1.396(8) . ?
C12 C16 1.362(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(8) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 180.000(1) . 2_666 ?
O1 Co1 O3 86.48(15) . 2_666 ?
O1 Co1 O3 93.52(16) 2_666 2_666 ?
O1 Co1 O3 86.48(15) 2_666 . ?
O1 Co1 O3 93.52(16) . . ?
O3 Co1 O3 180.000(1) . 2_666 ?
N3 Co1 O1 90.68(15) 2_566 2_666 ?
N3 Co1 O1 89.32(15) 1_655 2_666 ?
N3 Co1 O1 89.32(15) 2_566 . ?
N3 Co1 O1 90.68(15) 1_655 . ?
N3 Co1 O3 88.68(15) 2_566 2_666 ?
N3 Co1 O3 91.32(15) 1_655 2_666 ?
N3 Co1 O3 91.32(15) 2_566 . ?
N3 Co1 O3 88.68(15) 1_655 . ?
N3 Co1 N3 180.000(1) 1_655 2_566 ?
O2 Co2 O4 126.5(2) . . ?
O2 Co2 N1 111.89(18) . . ?
O2 Co2 N2 91.11(17) . 2_566 ?
O2 Co2 N4 89.54(17) . 2_556 ?
O4 Co2 N1 121.35(19) . . ?
O4 Co2 N2 92.35(16) . 2_566 ?
O4 Co2 N4 92.12(17) . 2_556 ?
N2 Co2 N1 80.33(15) 2_566 . ?
N4 Co2 N1 93.82(16) 2_556 . ?
N4 Co2 N2 173.92(16) 2_556 2_566 ?
C1 O1 Co1 150.4(4) . . ?
C1 O2 Co2 133.5(4) . . ?
C6 O3 Co1 152.1(4) . . ?
C6 O4 Co2 124.4(3) . . ?
C5 O5 H5 109.5 . . ?
C10 N1 Co2 106.3(3) . . ?
C10 N1 C11 100.6(4) . . ?
C11 N1 Co2 152.7(3) . . ?
N3 N2 Co2 146.1(3) . 2_566 ?
C10 N2 Co2 108.7(3) . 2_566 ?
C10 N2 N3 104.8(4) . . ?
N2 N3 Co1 110.7(3) . 1_455 ?
C11 N3 Co1 140.1(3) . 1_455 ?
C11 N3 N2 106.5(4) . . ?
C14 N4 Co2 118.8(4) . 2_556 ?
C14 N4 C15 117.6(4) . . ?
C15 N4 Co2 123.2(4) . 2_556 ?
O1 C1 O2 127.5(5) . . ?
O1 C1 C2 117.7(5) . . ?
O2 C1 C2 114.8(4) . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 C4 119.6(5) . 2_657 ?
C4 C2 C1 119.8(5) 2_657 . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C4 C3 120.0(5) 2_657 . ?
C2 C4 H4 120.0 2_657 . ?
C3 C4 H4 120.0 . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 125.9(5) . . ?
O3 C6 C7 119.2(5) . . ?
O4 C6 C7 114.8(5) . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 C9 119.9(5) . 2_665 ?
C9 C7 C6 120.9(5) 2_665 . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.5(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C9 C8 120.5(5) 2_665 . ?
C7 C9 H9 119.7 2_665 . ?
C8 C9 H9 119.7 . . ?
N1 C10 C10 123.3(6) . 2_566 ?
N2 C10 N1 115.9(4) . . ?
N2 C10 C10 120.8(6) . 2_566 ?
N1 C11 C12 123.8(4) . . ?
N3 C11 N1 112.3(4) . . ?
N3 C11 C12 123.8(4) . . ?
C13 C12 C11 120.7(5) . . ?
C16 C12 C11 120.5(5) . . ?
C16 C12 C13 118.6(5) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(5) . . ?
C14 C13 H13 120.7 . . ?
N4 C14 C13 122.9(5) . . ?
N4 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
N4 C15 H15 118.6 . . ?
N4 C15 C16 122.9(5) . . ?
C16 C15 H15 118.6 . . ?
C12 C16 C15 119.3(5) . . ?
C12 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?

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
Co1 O1 C1 O2 -0.6(12) . . . . ?
Co1 O1 C1 C2 179.0(5) . . . . ?
Co1 O3 C6 O4 -57.7(11) . . . . ?
Co1 O3 C6 C7 123.5(7) . . . . ?
Co1 N3 C11 N1 158.9(4) 1_455 . . . ?
Co1 N3 C11 C12 -24.2(8) 1_455 . . . ?
Co2 O2 C1 O1 -3.7(10) . . . . ?
Co2 O2 C1 C2 176.7(4) . . . . ?
Co2 O4 C6 O3 8.6(8) . . . . ?
Co2 O4 C6 C7 -172.5(4) . . . . ?
Co2 N1 C10 N2 -173.9(4) . . . . ?
Co2 N1 C10 C10 3.8(8) . . . 2_566 ?
Co2 N1 C11 N3 168.8(6) . . . . ?
Co2 N1 C11 C12 -8.2(11) . . . . ?
Co2 N2 N3 Co1 4.8(7) 2_566 . . 1_455 ?
Co2 N2 N3 C11 170.3(5) 2_566 . . . ?
Co2 N2 C10 N1 -175.1(4) 2_566 . . . ?
Co2 N2 C10 C10 7.1(8) 2_566 . . 2_566 ?
Co2 N4 C14 C13 -171.6(5) 2_556 . . . ?
Co2 N4 C15 C16 172.0(5) 2_556 . . . ?
O1 Co1 O1 C1 118(100) 2_666 . . . ?
O1 Co1 O3 C6 89.4(8) . . . . ?
O1 Co1 O3 C6 -90.6(8) 2_666 . . . ?
O1 C1 C2 C3 2.9(9) . . . . ?
O1 C1 C2 C4 -178.1(6) . . . 2_657 ?
O2 Co2 O4 C6 -45.6(5) . . . . ?
O2 Co2 N1 C10 81.9(4) . . . . ?
O2 Co2 N1 C11 -87.6(8) . . . . ?
O2 C1 C2 C3 -177.5(6) . . . . ?
O2 C1 C2 C4 1.6(8) . . . 2_657 ?
O3 Co1 O1 C1 -37.0(8) . . . . ?
O3 Co1 O1 C1 143.0(8) 2_666 . . . ?
O3 Co1 O3 C6 -123(100) 2_666 . . . ?
O3 C6 C7 C8 -0.7(9) . . . . ?
O3 C6 C7 C9 -179.2(6) . . . 2_665 ?
O4 Co2 O2 C1 56.3(6) . . . . ?
O4 Co2 N1 C10 -92.3(4) . . . . ?
O4 Co2 N1 C11 98.3(8) . . . . ?
O4 C6 C7 C8 -179.7(6) . . . . ?
O4 C6 C7 C9 1.8(8) . . . 2_665 ?
N1 Co2 O2 C1 -117.4(6) . . . . ?
N1 Co2 O4 C6 127.6(5) . . . . ?
N1 C11 C12 C13 -57.5(7) . . . . ?
N1 C11 C12 C16 119.5(6) . . . . ?
N2 Co2 O2 C1 -37.4(6) 2_566 . . . ?
N2 Co2 O4 C6 47.5(5) 2_566 . . . ?
N2 Co2 N1 C10 -5.4(3) 2_566 . . . ?
N2 Co2 N1 C11 -174.9(8) 2_566 . . . ?
N2 N3 C11 N1 0.4(5) . . . . ?
N2 N3 C11 C12 177.3(5) . . . . ?
N3 Co1 O1 C1 -125.7(8) 1_655 . . . ?
N3 Co1 O1 C1 54.3(8) 2_566 . . . ?
N3 Co1 O3 C6 -180.0(8) 1_655 . . . ?
N3 Co1 O3 C6 0.0(8) 2_566 . . . ?
N3 N2 C10 N1 -1.0(6) . . . . ?
N3 N2 C10 C10 -178.8(6) . . . 2_566 ?
N3 C11 C12 C13 125.9(6) . . . . ?
N3 C11 C12 C16 -57.1(8) . . . . ?
N4 Co2 O2 C1 148.6(6) 2_556 . . . ?
N4 Co2 O4 C6 -136.6(5) 2_556 . . . ?
N4 Co2 N1 C10 172.9(3) 2_556 . . . ?
N4 Co2 N1 C11 3.5(8) 2_556 . . . ?
N4 C15 C16 C12 -1.0(10) . . . . ?
C1 C2 C3 C4 -180.0(6) . . . . ?
C2 C3 C4 C2 -1.0(12) . . . 2_657 ?
C4 C2 C3 C4 1.0(12) 2_657 . . . ?
C6 C7 C8 C9 -178.8(6) . . . . ?
C7 C8 C9 C7 0.3(12) . . . 2_665 ?
C9 C7 C8 C9 -0.3(12) 2_665 . . . ?
C10 N1 C11 N3 -0.9(5) . . . . ?
C10 N1 C11 C12 -177.9(5) . . . . ?
C10 N2 N3 Co1 -165.1(3) . . . 1_455 ?
C10 N2 N3 C11 0.4(5) . . . . ?
C11 N1 C10 N2 1.2(6) . . . . ?
C11 N1 C10 C10 178.9(6) . . . 2_566 ?
C11 C12 C13 C14 175.8(5) . . . . ?
C11 C12 C16 C15 -175.1(5) . . . . ?
C12 C13 C14 N4 -0.5(9) . . . . ?
C13 C12 C16 C15 2.0(9) . . . . ?
C14 N4 C15 C16 -0.7(9) . . . . ?
C15 N4 C14 C13 1.4(9) . . . . ?
C16 C12 C13 C14 -1.2(8) . . . . ?

####################################################################### 
# 
# 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_2011073101ypf
_database_code_depnum_ccdc_archive 'CCDC 1033517'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2011-07-31
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C14 H9 Co0.5 N8), 2(H2 O)'
_chemical_formula_sum            'C28 H22 Co N16 O2'
_chemical_formula_weight         673.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H30 N8 Co1'
_chemical_oxdiff_usercomment     'C H N O Co'
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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2567(10)
_cell_length_b                   15.269(4)
_cell_length_c                   10.2578(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.720(5)
_cell_angle_gamma                90.00
_cell_volume                     1439.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6294
_cell_measurement_theta_min      2.8004
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6210
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1623
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00   52.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.3518    0.0000 -120.0000 294

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   14.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.3518   86.0000 -126.0000 124

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   38.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5236   77.0000 -180.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0348078000
_diffrn_orient_matrix_UB_12      0.0412898000
_diffrn_orient_matrix_UB_13      -0.0093401000
_diffrn_orient_matrix_UB_21      -0.0017625000
_diffrn_orient_matrix_UB_22      0.0037341000
_diffrn_orient_matrix_UB_23      0.0687107000
_diffrn_orient_matrix_UB_31      0.0689059000
_diffrn_orient_matrix_UB_32      0.0209610000
_diffrn_orient_matrix_UB_33      0.0062551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2424
_reflns_number_total             2938
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.9642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0963
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5000 0.0000 1.0000 0.01996(13) Uani 1 2 d S . .
O1 O 0.4045(2) 0.17386(18) 0.6485(3) 0.0711(8) Uani 1 1 d D . .
H1A H 0.483(3) 0.171(3) 0.702(3) 0.107 Uiso 1 1 d D . .
H1B H 0.405(4) 0.2194(17) 0.601(3) 0.107 Uiso 1 1 d D . .
N1 N -0.2197(3) 0.1469(2) 0.4412(3) 0.0610(8) Uani 1 1 d . . .
N2 N 0.2310(2) 0.06402(13) 0.76115(19) 0.0286(4) Uani 1 1 d . . .
H2 H 0.2709 0.1058 0.7220 0.034 Uiso 1 1 calc R . .
N3 N 0.0633(2) -0.02739(14) 0.8135(2) 0.0321(5) Uani 1 1 d . . .
N4 N 0.29841(19) 0.01396(12) 0.85867(18) 0.0230(4) Uani 1 1 d . . .
N5 N 0.35847(19) -0.09604(12) 1.06339(18) 0.0240(4) Uani 1 1 d . . .
N6 N 0.36245(19) -0.16062(12) 1.15532(18) 0.0261(4) Uani 1 1 d . . .
N7 N 0.1453(2) -0.16787(13) 1.0299(2) 0.0309(5) Uani 1 1 d . . .
N8 N 0.08829(19) -0.40315(12) 1.37423(19) 0.0267(4) Uani 1 1 d . . .
C1 C -0.0829(3) 0.1741(2) 0.4557(3) 0.0580(9) Uani 1 1 d . . .
H1 H -0.0563 0.2174 0.3994 0.070 Uiso 1 1 calc R . .
C2 C 0.0225(3) 0.1416(2) 0.5495(3) 0.0476(7) Uani 1 1 d . . .
H2A H 0.1171 0.1631 0.5559 0.057 Uiso 1 1 calc R . .
C3 C -0.0140(3) 0.07705(17) 0.6338(2) 0.0325(5) Uani 1 1 d . . .
C4 C -0.1565(3) 0.0488(2) 0.6199(3) 0.0481(7) Uani 1 1 d . . .
H4 H -0.1866 0.0057 0.6749 0.058 Uiso 1 1 calc R . .
C5 C -0.2538(3) 0.0856(2) 0.5229(3) 0.0600(9) Uani 1 1 d . . .
H5 H -0.3495 0.0659 0.5146 0.072 Uiso 1 1 calc R . .
C6 C 0.0918(2) 0.03826(16) 0.7349(2) 0.0299(5) Uani 1 1 d . . .
C7 C 0.1923(2) -0.04007(15) 0.8864(2) 0.0252(5) Uani 1 1 d . . .
C8 C 0.2279(2) -0.10287(15) 0.9919(2) 0.0249(5) Uani 1 1 d . . .
C9 C 0.2342(2) -0.20113(15) 1.1325(2) 0.0269(5) Uani 1 1 d . . .
C10 C 0.1884(2) -0.27194(15) 1.2140(2) 0.0290(5) Uani 1 1 d . . .
C11 C 0.0431(3) -0.29625(19) 1.2025(3) 0.0426(7) Uani 1 1 d . . .
H11 H -0.0242 -0.2695 1.1406 0.051 Uiso 1 1 calc R . .
C12 C -0.0005(3) -0.36030(19) 1.2835(3) 0.0418(7) Uani 1 1 d . . .
H12 H -0.0987 -0.3749 1.2747 0.050 Uiso 1 1 calc R . .
C13 C 0.2283(3) -0.38037(18) 1.3818(3) 0.0418(7) Uani 1 1 d . . .
H13 H 0.2939 -0.4094 1.4425 0.050 Uiso 1 1 calc R . .
C14 C 0.2817(3) -0.31661(18) 1.3054(3) 0.0438(7) Uani 1 1 d . . .
H14 H 0.3806 -0.3037 1.3154 0.053 Uiso 1 1 calc R . .


_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 N4 2.2352(18) 3_657 ?
Co1 N4 2.2352(18) . ?
Co1 N5 2.1188(18) 3_657 ?
Co1 N5 2.1188(18) . ?
Co1 N8 2.1832(18) 4_655 ?
Co1 N8 2.1832(18) 2_557 ?
O1 H1A 0.858(10) . ?
O1 H1B 0.848(10) . ?
N1 C1 1.324(4) . ?
N1 C5 1.319(4) . ?
N2 H2 0.8600 . ?
N2 N4 1.352(3) . ?
N2 C6 1.344(3) . ?
N3 C6 1.332(3) . ?
N3 C7 1.346(3) . ?
N4 C7 1.338(3) . ?
N5 N6 1.362(3) . ?
N5 C8 1.342(3) . ?
N6 C9 1.334(3) . ?
N7 C8 1.339(3) . ?
N7 C9 1.356(3) . ?
N8 Co1 2.1832(18) 2_547 ?
N8 C12 1.338(3) . ?
N8 C13 1.335(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.379(4) . ?
C3 C4 1.380(4) . ?
C3 C6 1.466(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.454(3) . ?
C9 C10 1.460(3) . ?
C10 C11 1.387(3) . ?
C10 C14 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Co1 N4 180.0 . 3_657 ?
N5 Co1 N4 103.54(7) 3_657 . ?
N5 Co1 N4 76.46(7) . . ?
N5 Co1 N4 76.46(7) 3_657 3_657 ?
N5 Co1 N4 103.54(7) . 3_657 ?
N5 Co1 N5 180.00(7) 3_657 . ?
N5 Co1 N8 90.01(7) 3_657 2_557 ?
N5 Co1 N8 89.99(7) . 2_557 ?
N5 Co1 N8 89.99(7) 3_657 4_655 ?
N5 Co1 N8 90.01(7) . 4_655 ?
N8 Co1 N4 91.33(7) 2_557 3_657 ?
N8 Co1 N4 88.67(7) 4_655 3_657 ?
N8 Co1 N4 91.33(7) 4_655 . ?
N8 Co1 N4 88.67(7) 2_557 . ?
N8 Co1 N8 180.0 2_557 4_655 ?
H1A O1 H1B 110(2) . . ?
C5 N1 C1 116.6(3) . . ?
N4 N2 H2 125.3 . . ?
C6 N2 H2 125.3 . . ?
C6 N2 N4 109.35(18) . . ?
C6 N3 C7 102.63(19) . . ?
N2 N4 Co1 144.27(14) . . ?
C7 N4 Co1 112.41(14) . . ?
C7 N4 N2 102.65(17) . . ?
N6 N5 Co1 138.25(14) . . ?
C8 N5 Co1 115.81(14) . . ?
C8 N5 N6 105.78(17) . . ?
C9 N6 N5 105.23(17) . . ?
C8 N7 C9 100.84(18) . . ?
C12 N8 Co1 120.00(15) . 2_547 ?
C13 N8 Co1 124.75(16) . 2_547 ?
C13 N8 C12 115.2(2) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.7(3) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 117.4(2) . . ?
C2 C3 C6 122.7(2) . . ?
C4 C3 C6 119.9(2) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 124.2(3) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N2 C6 C3 124.7(2) . . ?
N3 C6 N2 110.6(2) . . ?
N3 C6 C3 124.7(2) . . ?
N3 C7 C8 128.1(2) . . ?
N4 C7 N3 114.7(2) . . ?
N4 C7 C8 117.14(19) . . ?
N5 C8 C7 117.82(19) . . ?
N7 C8 N5 114.0(2) . . ?
N7 C8 C7 128.2(2) . . ?
N6 C9 N7 114.2(2) . . ?
N6 C9 C10 123.7(2) . . ?
N7 C9 C10 122.1(2) . . ?
C11 C10 C9 119.5(2) . . ?
C14 C10 C9 123.7(2) . . ?
C14 C10 C11 116.7(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
N8 C12 C11 124.6(2) . . ?
N8 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
N8 C13 H13 117.9 . . ?
N8 C13 C14 124.2(2) . . ?
C14 C13 H13 117.9 . . ?
C10 C14 H14 120.1 . . ?
C13 C14 C10 119.9(2) . . ?
C13 C14 H14 120.1 . . ?

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
Co1 N4 C7 N3 172.80(16) . . . . ?
Co1 N4 C7 C8 -5.7(2) . . . . ?
Co1 N5 N6 C9 -175.08(18) . . . . ?
Co1 N5 C8 N7 176.01(15) . . . . ?
Co1 N5 C8 C7 -4.9(3) . . . . ?
Co1 N8 C12 C11 177.8(2) 2_547 . . . ?
Co1 N8 C13 C14 -177.3(2) 2_547 . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
N2 N4 C7 N3 -0.1(3) . . . . ?
N2 N4 C7 C8 -178.60(19) . . . . ?
N3 C7 C8 N5 -171.0(2) . . . . ?
N3 C7 C8 N7 8.0(4) . . . . ?
N4 Co1 N4 N2 -156(100) 3_657 . . . ?
N4 Co1 N4 C7 35(100) 3_657 . . . ?
N4 Co1 N5 N6 175.9(2) . . . . ?
N4 Co1 N5 N6 -4.1(2) 3_657 . . . ?
N4 Co1 N5 C8 -178.60(16) 3_657 . . . ?
N4 Co1 N5 C8 1.40(16) . . . . ?
N4 N2 C6 N3 0.7(3) . . . . ?
N4 N2 C6 C3 -179.3(2) . . . . ?
N4 C7 C8 N5 7.3(3) . . . . ?
N4 C7 C8 N7 -173.8(2) . . . . ?
N5 Co1 N4 N2 -9.5(3) 3_657 . . . ?
N5 Co1 N4 N2 170.5(3) . . . . ?
N5 Co1 N4 C7 -177.59(15) 3_657 . . . ?
N5 Co1 N4 C7 2.41(15) . . . . ?
N5 Co1 N5 N6 64(100) 3_657 . . . ?
N5 Co1 N5 C8 -110(100) 3_657 . . . ?
N5 N6 C9 N7 0.5(3) . . . . ?
N5 N6 C9 C10 -176.2(2) . . . . ?
N6 N5 C8 N7 -0.2(3) . . . . ?
N6 N5 C8 C7 178.88(19) . . . . ?
N6 C9 C10 C11 165.0(2) . . . . ?
N6 C9 C10 C14 -14.0(4) . . . . ?
N7 C9 C10 C11 -11.5(4) . . . . ?
N7 C9 C10 C14 169.5(3) . . . . ?
N8 Co1 N4 N2 -99.8(2) 4_655 . . . ?
N8 Co1 N4 N2 80.2(2) 2_557 . . . ?
N8 Co1 N4 C7 92.11(16) 4_655 . . . ?
N8 Co1 N4 C7 -87.89(16) 2_557 . . . ?
N8 Co1 N5 N6 -95.4(2) 2_557 . . . ?
N8 Co1 N5 N6 84.6(2) 4_655 . . . ?
N8 Co1 N5 C8 90.04(16) 2_557 . . . ?
N8 Co1 N5 C8 -89.96(16) 4_655 . . . ?
N8 C13 C14 C10 -0.1(5) . . . . ?
C1 N1 C5 C4 -0.3(6) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C6 179.2(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C6 N2 3.8(4) . . . . ?
C2 C3 C6 N3 -176.2(3) . . . . ?
C3 C4 C5 N1 -0.1(6) . . . . ?
C4 C3 C6 N2 -176.4(3) . . . . ?
C4 C3 C6 N3 3.6(4) . . . . ?
C5 N1 C1 C2 0.2(6) . . . . ?
C6 N2 N4 Co1 -169.1(2) . . . . ?
C6 N2 N4 C7 -0.3(2) . . . . ?
C6 N3 C7 N4 0.5(3) . . . . ?
C6 N3 C7 C8 178.8(2) . . . . ?
C6 C3 C4 C5 -179.2(3) . . . . ?
C7 N3 C6 N2 -0.7(3) . . . . ?
C7 N3 C6 C3 179.3(2) . . . . ?
C8 N5 N6 C9 -0.2(2) . . . . ?
C8 N7 C9 N6 -0.6(3) . . . . ?
C8 N7 C9 C10 176.2(2) . . . . ?
C9 N7 C8 N5 0.5(3) . . . . ?
C9 N7 C8 C7 -178.5(2) . . . . ?
C9 C10 C11 C12 -177.2(3) . . . . ?
C9 C10 C14 C13 177.5(3) . . . . ?
C10 C11 C12 N8 -0.8(5) . . . . ?
C11 C10 C14 C13 -1.5(4) . . . . ?
C12 N8 C13 C14 1.2(4) . . . . ?
C13 N8 C12 C11 -0.7(4) . . . . ?
C14 C10 C11 C12 1.9(4) . . . . ?

####################################################################### 
# 
# 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_0115-ypf-007a
_database_code_depnum_ccdc_archive 'CCDC 1033518'

_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2012-02-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H9 N8 Ni0.5), 2(H2 O)'
_chemical_formula_sum            'C28 H22 N16 Ni O2'
_chemical_formula_weight         673.33
_chemical_melting_point          ?
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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1787(10)
_cell_length_b                   15.2181(11)
_cell_length_c                   10.3355(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.657(8)
_cell_angle_gamma                90.00
_cell_volume                     1433.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0948
_cell_measurement_theta_min      2.8055
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            reseda
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11641
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1623
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00   -3.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6427  -57.0000  -90.0000 166

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00    3.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6427  -57.0000 -180.0000 116

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00  -37.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6427 -178.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   52.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6427   77.0000   30.0000 198

#__ type_ start__ end____ width___ exp.time_
  5 omega  -34.00   38.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6427   57.0000 -180.0000 144

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   32.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8146   89.0000  128.0000 86

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   76.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8146  178.0000    0.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0135194000
_diffrn_orient_matrix_UB_12      -0.0146414000
_diffrn_orient_matrix_UB_13      -0.0626803000
_diffrn_orient_matrix_UB_21      0.0388607000
_diffrn_orient_matrix_UB_22      0.0394095000
_diffrn_orient_matrix_UB_23      -0.0091158000
_diffrn_orient_matrix_UB_31      0.0660268000
_diffrn_orient_matrix_UB_32      -0.0201605000
_diffrn_orient_matrix_UB_33      0.0276869000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1951
_reflns_number_total             2922
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1073
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Ni1 Ni 0.5000 0.0000 1.0000 0.01941(18) Uani 1 2 d S . .
O1 O 0.4039(3) 0.1736(2) 0.6454(3) 0.0708(11) Uani 1 1 d D . .
H1A H 0.478(4) 0.178(3) 0.704(3) 0.106 Uiso 1 1 d D . .
H1B H 0.398(5) 0.2187(19) 0.597(4) 0.106 Uiso 1 1 d D . .
N1 N 0.0858(3) -0.40378(17) 1.3774(2) 0.0243(7) Uani 1 1 d . . .
N2 N 0.3646(3) -0.15957(17) 1.1580(2) 0.0247(7) Uani 1 1 d . . .
N3 N 0.3612(3) -0.09515(16) 1.0655(2) 0.0215(6) Uani 1 1 d . . .
N4 N 0.1447(3) -0.16777(18) 1.0322(3) 0.0295(7) Uani 1 1 d . . .
N5 N 0.3020(3) 0.01406(16) 0.8623(2) 0.0219(7) Uani 1 1 d . . .
N6 N 0.2345(3) 0.06431(17) 0.7637(2) 0.0286(7) Uani 1 1 d . . .
H6 H 0.2754 0.1059 0.7247 0.034 Uiso 1 1 calc R . .
N7 N 0.0646(3) -0.02791(18) 0.8150(3) 0.0310(8) Uani 1 1 d . . .
N8 N -0.2187(4) 0.1444(3) 0.4398(3) 0.0601(11) Uani 1 1 d . . .
C1 C 0.2265(4) -0.3803(2) 1.3846(4) 0.0437(11) Uani 1 1 d . . .
H1 H 0.2926 -0.4088 1.4455 0.052 Uiso 1 1 calc R . .
C2 C 0.2816(4) -0.3164(2) 1.3079(4) 0.0446(11) Uani 1 1 d . . .
H2 H 0.3813 -0.3035 1.3182 0.054 Uiso 1 1 calc R . .
C3 C 0.1883(4) -0.2723(2) 1.2166(3) 0.0255(8) Uani 1 1 d . . .
C4 C 0.0422(4) -0.2967(3) 1.2052(3) 0.0438(11) Uani 1 1 d . . .
H4 H -0.0256 -0.2698 1.1438 0.053 Uiso 1 1 calc R . .
C5 C -0.0017(4) -0.3610(3) 1.2855(3) 0.0426(11) Uani 1 1 d . . .
H5 H -0.1006 -0.3762 1.2751 0.051 Uiso 1 1 calc R . .
C6 C 0.2346(4) -0.2006(2) 1.1352(3) 0.0260(8) Uani 1 1 d . . .
C7 C 0.2293(4) -0.1031(2) 0.9949(3) 0.0252(8) Uani 1 1 d . . .
C8 C 0.1943(4) -0.0406(2) 0.8890(3) 0.0237(8) Uani 1 1 d . . .
C9 C 0.0933(4) 0.0385(2) 0.7367(3) 0.0288(9) Uani 1 1 d . . .
C10 C -0.0124(4) 0.0765(2) 0.6346(3) 0.0316(9) Uani 1 1 d . . .
C11 C -0.1552(4) 0.0473(3) 0.6216(4) 0.0473(11) Uani 1 1 d . . .
H11 H -0.1850 0.0047 0.6774 0.057 Uiso 1 1 calc R . .
C12 C -0.2534(5) 0.0826(3) 0.5236(4) 0.0609(14) Uani 1 1 d . . .
H12 H -0.3496 0.0623 0.5154 0.073 Uiso 1 1 calc R . .
C13 C -0.0814(5) 0.1723(3) 0.4554(4) 0.0554(13) Uani 1 1 d . . .
H13 H -0.0548 0.2157 0.3993 0.067 Uiso 1 1 calc R . .
C14 C 0.0257(4) 0.1409(3) 0.5501(4) 0.0474(12) Uani 1 1 d . . .
H14 H 0.1209 0.1628 0.5566 0.057 Uiso 1 1 calc R . .


_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
Ni1 N1 2.145(3) 4_655 ?
Ni1 N1 2.145(3) 2_557 ?
Ni1 N3 2.092(3) 3_657 ?
Ni1 N3 2.092(3) . ?
Ni1 N5 2.185(2) 3_657 ?
Ni1 N5 2.185(2) . ?
O1 H1A 0.855(10) . ?
O1 H1B 0.848(10) . ?
N1 Ni1 2.145(3) 2_547 ?
N1 C1 1.334(4) . ?
N1 C5 1.340(4) . ?
N2 N3 1.367(3) . ?
N2 C6 1.343(4) . ?
N3 C7 1.345(4) . ?
N4 C6 1.363(4) . ?
N4 C7 1.337(4) . ?
N5 N6 1.365(3) . ?
N5 C8 1.344(4) . ?
N6 H6 0.8600 . ?
N6 C9 1.351(4) . ?
N7 C8 1.352(4) . ?
N7 C9 1.340(4) . ?
N8 C12 1.341(5) . ?
N8 C13 1.321(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 C4 1.383(5) . ?
C3 C6 1.470(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.458(4) . ?
C9 C10 1.467(4) . ?
C10 C11 1.375(5) . ?
C10 C14 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.389(5) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.000(1) 4_655 2_557 ?
N1 Ni1 N5 90.98(9) 4_655 . ?
N1 Ni1 N5 89.02(9) 2_557 . ?
N1 Ni1 N5 89.02(9) 4_655 3_657 ?
N1 Ni1 N5 90.98(9) 2_557 3_657 ?
N3 Ni1 N1 89.87(10) . 4_655 ?
N3 Ni1 N1 89.87(10) 3_657 2_557 ?
N3 Ni1 N1 90.13(10) . 2_557 ?
N3 Ni1 N1 90.13(10) 3_657 4_655 ?
N3 Ni1 N3 180.0 . 3_657 ?
N3 Ni1 N5 77.68(10) . . ?
N3 Ni1 N5 77.68(10) 3_657 3_657 ?
N3 Ni1 N5 102.32(10) . 3_657 ?
N3 Ni1 N5 102.32(10) 3_657 . ?
N5 Ni1 N5 180.0 3_657 . ?
H1A O1 H1B 110(2) . . ?
C1 N1 Ni1 124.7(2) . 2_547 ?
C1 N1 C5 114.0(3) . . ?
C5 N1 Ni1 121.3(2) . 2_547 ?
C6 N2 N3 105.2(2) . . ?
N2 N3 Ni1 139.19(19) . . ?
C7 N3 Ni1 115.5(2) . . ?
C7 N3 N2 105.1(3) . . ?
C7 N4 C6 100.1(3) . . ?
N6 N5 Ni1 144.4(2) . . ?
C8 N5 Ni1 112.46(19) . . ?
C8 N5 N6 102.6(2) . . ?
N5 N6 H6 125.3 . . ?
C9 N6 N5 109.4(3) . . ?
C9 N6 H6 125.3 . . ?
C9 N7 C8 103.1(3) . . ?
C13 N8 C12 116.2(3) . . ?
N1 C1 H1 117.6 . . ?
N1 C1 C2 124.8(3) . . ?
C2 C1 H1 117.6 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 116.6(3) . . ?
C2 C3 C6 123.9(3) . . ?
C4 C3 C6 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 125.5(3) . . ?
N1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
N2 C6 N4 114.3(3) . . ?
N2 C6 C3 123.7(3) . . ?
N4 C6 C3 122.0(3) . . ?
N3 C7 C8 117.0(3) . . ?
N4 C7 N3 115.2(3) . . ?
N4 C7 C8 127.8(3) . . ?
N5 C8 N7 114.6(3) . . ?
N5 C8 C7 117.0(3) . . ?
N7 C8 C7 128.3(3) . . ?
N6 C9 C10 124.9(3) . . ?
N7 C9 N6 110.2(3) . . ?
N7 C9 C10 124.9(3) . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 C14 118.3(3) . . ?
C14 C10 C9 122.6(3) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(4) . . ?
C12 C11 H11 120.7 . . ?
N8 C12 C11 124.1(4) . . ?
N8 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N8 C13 H13 117.9 . . ?
N8 C13 C14 124.2(4) . . ?
C14 C13 H13 117.9 . . ?
C10 C14 C13 118.5(4) . . ?
C10 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?

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
Ni1 N1 C1 C2 -178.1(3) 2_547 . . . ?
Ni1 N1 C5 C4 177.9(3) 2_547 . . . ?
Ni1 N3 C7 N4 175.9(2) . . . . ?
Ni1 N3 C7 C8 -4.8(4) . . . . ?
Ni1 N5 N6 C9 -169.8(3) . . . . ?
Ni1 N5 C8 N7 173.4(2) . . . . ?
Ni1 N5 C8 C7 -4.7(4) . . . . ?
N1 Ni1 N3 N2 85.2(3) 4_655 . . . ?
N1 Ni1 N3 N2 -94.8(3) 2_557 . . . ?
N1 Ni1 N3 C7 -89.3(2) 4_655 . . . ?
N1 Ni1 N3 C7 90.7(2) 2_557 . . . ?
N1 Ni1 N5 N6 80.8(4) 2_557 . . . ?
N1 Ni1 N5 N6 -99.2(4) 4_655 . . . ?
N1 Ni1 N5 C8 91.3(2) 4_655 . . . ?
N1 Ni1 N5 C8 -88.7(2) 2_557 . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
N2 N3 C7 N4 -0.3(4) . . . . ?
N2 N3 C7 C8 179.0(3) . . . . ?
N3 Ni1 N3 N2 24(100) 3_657 . . . ?
N3 Ni1 N3 C7 -150(100) 3_657 . . . ?
N3 Ni1 N5 N6 171.1(4) . . . . ?
N3 Ni1 N5 N6 -8.9(4) 3_657 . . . ?
N3 Ni1 N5 C8 1.7(2) . . . . ?
N3 Ni1 N5 C8 -178.3(2) 3_657 . . . ?
N3 N2 C6 N4 0.5(4) . . . . ?
N3 N2 C6 C3 -177.0(3) . . . . ?
N3 C7 C8 N5 6.5(5) . . . . ?
N3 C7 C8 N7 -171.3(3) . . . . ?
N4 C7 C8 N5 -174.4(3) . . . . ?
N4 C7 C8 N7 7.9(6) . . . . ?
N5 Ni1 N3 N2 176.2(3) . . . . ?
N5 Ni1 N3 N2 -3.8(3) 3_657 . . . ?
N5 Ni1 N3 C7 1.8(2) . . . . ?
N5 Ni1 N3 C7 -178.2(2) 3_657 . . . ?
N5 Ni1 N5 N6 54(100) 3_657 . . . ?
N5 Ni1 N5 C8 -116(100) 3_657 . . . ?
N5 N6 C9 N7 0.0(4) . . . . ?
N5 N6 C9 C10 -178.8(3) . . . . ?
N6 N5 C8 N7 -0.4(4) . . . . ?
N6 N5 C8 C7 -178.4(3) . . . . ?
N6 C9 C10 C11 -176.7(4) . . . . ?
N6 C9 C10 C14 3.4(6) . . . . ?
N7 C9 C10 C11 4.7(6) . . . . ?
N7 C9 C10 C14 -175.2(4) . . . . ?
N8 C13 C14 C10 -0.2(7) . . . . ?
C1 N1 C5 C4 -1.6(6) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C1 C2 C3 C6 176.8(4) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C2 C3 C6 N2 -13.2(6) . . . . ?
C2 C3 C6 N4 169.5(3) . . . . ?
C3 C4 C5 N1 0.3(7) . . . . ?
C4 C3 C6 N2 165.0(3) . . . . ?
C4 C3 C6 N4 -12.2(5) . . . . ?
C5 N1 C1 C2 1.4(6) . . . . ?
C6 N2 N3 Ni1 -174.9(3) . . . . ?
C6 N2 N3 C7 -0.1(3) . . . . ?
C6 N4 C7 N3 0.5(4) . . . . ?
C6 N4 C7 C8 -178.6(3) . . . . ?
C6 C3 C4 C5 -177.1(4) . . . . ?
C7 N4 C6 N2 -0.6(4) . . . . ?
C7 N4 C6 C3 176.9(3) . . . . ?
C8 N5 N6 C9 0.2(3) . . . . ?
C8 N7 C9 N6 -0.2(4) . . . . ?
C8 N7 C9 C10 178.6(3) . . . . ?
C9 N7 C8 N5 0.3(4) . . . . ?
C9 N7 C8 C7 178.1(3) . . . . ?
C9 C10 C11 C12 -179.0(4) . . . . ?
C9 C10 C14 C13 179.2(4) . . . . ?
C10 C11 C12 N8 -0.2(7) . . . . ?
C11 C10 C14 C13 -0.7(6) . . . . ?
C12 N8 C13 C14 0.9(7) . . . . ?
C13 N8 C12 C11 -0.7(7) . . . . ?
C14 C10 C11 C12 0.9(6) . . . . ?

####################################################################### 
# 
# 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_0226-ypf-013
_database_code_depnum_ccdc_archive 'CCDC 1033519'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2014-11-07
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H8 Cu2 N8, O'
_chemical_formula_sum            'C14 H8 Cu2 N8 O'
_chemical_formula_weight         431.36
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y, z-1/2'

_cell_length_a                   14.6978(14)
_cell_length_b                   19.3933(17)
_cell_length_c                   10.3560(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2951.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0851
_cell_measurement_theta_min      2.7647
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12075
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.77
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1623
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    1.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7990  -57.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   45.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7990   77.0000   60.0000 178

#__ type_ start__ end____ width___ exp.time_
  3 omega  -73.00   12.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.7990  -77.0000    0.0000 170

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00  -25.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9709  -57.0000  -90.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0477145000
_diffrn_orient_matrix_UB_12      -0.0030333000
_diffrn_orient_matrix_UB_13      0.0088239000
_diffrn_orient_matrix_UB_21      -0.0045108000
_diffrn_orient_matrix_UB_22      -0.0363622000
_diffrn_orient_matrix_UB_23      0.0050564000
_diffrn_orient_matrix_UB_31      0.0058689000
_diffrn_orient_matrix_UB_32      -0.0031419000
_diffrn_orient_matrix_UB_33      -0.0675672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2123
_reflns_number_total             3018
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0524P)²+5.9026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1390
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.0000 0.26499(4) 0.2500 0.0259(2) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.50941(4) 0.7500 0.0243(2) Uani 1 2 d S . .
Cu3 Cu 0.34552(5) 0.38215(3) 0.75452(6) 0.0316(2) Uani 1 1 d . . .
O1 O 0.010(3) 0.526(3) 0.445(5) 0.42(4) Uiso 0.50(4) 1 d P . 2
O2 O 0.0000 0.580(4) 0.2500 0.82(7) Uiso 1.00(7) 2 d S . 1
N1 N 0.0947(3) 0.33589(19) 0.3296(4) 0.0290(10) Uani 1 1 d . . .
N2 N 0.3276(3) 0.52242(17) 0.4449(3) 0.0177(8) Uani 1 1 d . . .
N3 N 0.3442(3) 0.45002(17) 0.6134(3) 0.0165(8) Uani 1 1 d . . .
N4 N 0.4065(3) 0.50304(17) 0.6251(3) 0.0164(8) Uani 1 1 d . . .
N5 N 0.5097(3) 0.62976(18) 0.5822(4) 0.0198(9) Uani 1 1 d . . .
N6 N 0.4423(3) 0.64023(16) 0.3883(3) 0.0159(8) Uani 1 1 d . . .
N7 N 0.5033(3) 0.69355(17) 0.4000(4) 0.0168(8) Uani 1 1 d . . .
N8 N 0.7421(3) 0.8177(2) 0.6824(4) 0.0332(11) Uani 1 1 d . . .
C1 C 0.1271(4) 0.3929(3) 0.2719(5) 0.0355(14) Uani 1 1 d . . .
H1 H 0.1037 0.4045 0.1913 0.043 Uiso 1 1 calc R . .
C2 C 0.1930(4) 0.4353(2) 0.3247(5) 0.0353(14) Uani 1 1 d . . .
H2 H 0.2145 0.4730 0.2783 0.042 Uiso 1 1 calc R . .
C3 C 0.2266(3) 0.4216(2) 0.4465(4) 0.0216(10) Uani 1 1 d . . .
C4 C 0.1894(4) 0.3653(3) 0.5104(5) 0.0428(16) Uani 1 1 d . . .
H4 H 0.2070 0.3553 0.5946 0.051 Uiso 1 1 calc R . .
C5 C 0.1260(4) 0.3243(3) 0.4481(5) 0.0436(16) Uani 1 1 d . . .
H5 H 0.1038 0.2860 0.4921 0.052 Uiso 1 1 calc R . .
C6 C 0.2992(3) 0.4642(2) 0.5036(4) 0.0164(9) Uani 1 1 d . . .
C7 C 0.3934(3) 0.5431(2) 0.5229(4) 0.0154(9) Uani 1 1 d . . .
C8 C 0.4486(3) 0.6049(2) 0.4978(4) 0.0167(9) Uani 1 1 d . . .
C9 C 0.5408(3) 0.6851(2) 0.5178(4) 0.0203(10) Uani 1 1 d . . .
C10 C 0.6086(3) 0.7319(2) 0.5737(4) 0.0234(11) Uani 1 1 d . . .
C11 C 0.6349(4) 0.7923(3) 0.5148(5) 0.0389(14) Uani 1 1 d . . .
H11 H 0.6089 0.8053 0.4367 0.047 Uiso 1 1 calc R . .
C12 C 0.7005(4) 0.8339(3) 0.5722(5) 0.0448(16) Uani 1 1 d . . .
H12 H 0.7161 0.8750 0.5317 0.054 Uiso 1 1 calc R . .
C13 C 0.7160(4) 0.7587(3) 0.7386(5) 0.0324(13) Uani 1 1 d . . .
H13 H 0.7440 0.7464 0.8158 0.039 Uiso 1 1 calc R . .
C14 C 0.6505(4) 0.7150(3) 0.6896(5) 0.0328(13) Uani 1 1 d . . .
H14 H 0.6346 0.6749 0.7335 0.039 Uiso 1 1 calc R . .


_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
Cu1 N1 2.123(4) . ?
Cu1 N1 2.123(4) 4 ?
Cu1 N7 2.082(4) 7_655 ?
Cu1 N7 2.082(4) 6_556 ?
Cu2 N4 1.891(4) . ?
Cu2 N4 1.891(4) 4_656 ?
Cu3 N3 1.967(3) . ?
Cu3 N6 2.033(4) 8_566 ?
Cu3 N8 2.074(4) 6_557 ?
O1 O1 1.55(9) 5_566 ?
N1 C1 1.343(6) . ?
N1 C5 1.330(6) . ?
N2 C6 1.348(5) . ?
N2 C7 1.322(5) . ?
N3 N4 1.382(5) . ?
N3 C6 1.344(5) . ?
N4 C7 1.327(5) . ?
N5 C8 1.343(6) . ?
N5 C9 1.343(6) . ?
N6 Cu3 2.033(4) 8_565 ?
N6 N7 1.373(5) . ?
N6 C8 1.329(5) . ?
N7 Cu1 2.082(4) 6_666 ?
N7 C9 1.349(6) . ?
N8 Cu3 2.074(4) 6_667 ?
N8 C12 1.332(7) . ?
N8 C13 1.340(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(6) . ?
C3 C4 1.387(6) . ?
C3 C6 1.474(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(7) . ?
C5 H5 0.9300 . ?
C7 C8 1.469(6) . ?
C9 C10 1.467(6) . ?
C10 C11 1.375(7) . ?
C10 C14 1.389(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.380(7) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 99.3(2) . 4 ?
N7 Cu1 N1 134.85(15) 6_556 . ?
N7 Cu1 N1 99.00(14) 7_655 . ?
N7 Cu1 N1 134.85(15) 7_655 4 ?
N7 Cu1 N1 99.00(14) 6_556 4 ?
N7 Cu1 N7 96.58(19) 6_556 7_655 ?
N4 Cu2 N4 172.5(2) . 4_656 ?
N3 Cu3 N6 130.99(15) . 8_566 ?
N3 Cu3 N8 129.10(16) . 6_557 ?
N6 Cu3 N8 99.76(16) 8_566 6_557 ?
C1 N1 Cu1 126.3(3) . . ?
C5 N1 Cu1 118.3(3) . . ?
C5 N1 C1 115.3(4) . . ?
C7 N2 C6 101.9(3) . . ?
N4 N3 Cu3 115.2(3) . . ?
C6 N3 Cu3 140.4(3) . . ?
C6 N3 N4 104.4(3) . . ?
N3 N4 Cu2 126.1(3) . . ?
C7 N4 Cu2 127.8(3) . . ?
C7 N4 N3 105.6(3) . . ?
C9 N5 C8 101.0(4) . . ?
N7 N6 Cu3 132.7(3) . 8_565 ?
C8 N6 Cu3 121.3(3) . 8_565 ?
C8 N6 N7 105.5(3) . . ?
N6 N7 Cu1 114.8(3) . 6_666 ?
C9 N7 Cu1 140.0(3) . 6_666 ?
C9 N7 N6 104.8(3) . . ?
C12 N8 Cu3 117.6(3) . 6_667 ?
C12 N8 C13 116.3(4) . . ?
C13 N8 Cu3 126.0(4) . 6_667 ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.2(5) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 116.5(4) . . ?
C2 C3 C6 121.1(4) . . ?
C4 C3 C6 122.3(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 124.4(5) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N2 C6 C3 120.9(4) . . ?
N3 C6 N2 113.6(4) . . ?
N3 C6 C3 125.5(4) . . ?
N2 C7 N4 114.5(4) . . ?
N2 C7 C8 122.9(4) . . ?
N4 C7 C8 122.6(4) . . ?
N5 C8 C7 123.2(4) . . ?
N6 C8 N5 114.6(4) . . ?
N6 C8 C7 122.2(4) . . ?
N5 C9 N7 114.1(4) . . ?
N5 C9 C10 122.0(4) . . ?
N7 C9 C10 123.9(4) . . ?
C11 C10 C9 122.9(4) . . ?
C11 C10 C14 117.4(4) . . ?
C14 C10 C9 119.6(4) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
N8 C12 C11 123.2(5) . . ?
N8 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N8 C13 H13 117.8 . . ?
N8 C13 C14 124.4(5) . . ?
C14 C13 H13 117.8 . . ?
C10 C14 H14 120.6 . . ?
C13 C14 C10 118.8(5) . . ?
C13 C14 H14 120.6 . . ?

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
Cu1 N1 C1 C2 -176.0(5) . . . . ?
Cu1 N1 C5 C4 178.5(5) . . . . ?
Cu1 N7 C9 N5 172.1(3) 6_666 . . . ?
Cu1 N7 C9 C10 -6.9(8) 6_666 . . . ?
Cu2 N4 C7 N2 173.6(3) . . . . ?
Cu2 N4 C7 C8 -5.6(6) . . . . ?
Cu3 N3 N4 Cu2 8.2(4) . . . . ?
Cu3 N3 N4 C7 -178.9(3) . . . . ?
Cu3 N3 C6 N2 177.7(3) . . . . ?
Cu3 N3 C6 C3 -3.6(8) . . . . ?
Cu3 N6 N7 Cu1 -2.0(5) 8_565 . . 6_666 ?
Cu3 N6 N7 C9 171.8(3) 8_565 . . . ?
Cu3 N6 C8 N5 -173.7(3) 8_565 . . . ?
Cu3 N6 C8 C7 7.0(6) 8_565 . . . ?
Cu3 N8 C12 C11 175.1(5) 6_667 . . . ?
Cu3 N8 C13 C14 -176.0(4) 6_667 . . . ?
N1 Cu1 N1 C1 -44.3(4) 4 . . . ?
N1 Cu1 N1 C5 135.4(5) 4 . . . ?
N1 C1 C2 C3 -2.8(10) . . . . ?
N2 C7 C8 N5 173.7(4) . . . . ?
N2 C7 C8 N6 -7.2(7) . . . . ?
N3 N4 C7 N2 0.8(5) . . . . ?
N3 N4 C7 C8 -178.4(4) . . . . ?
N4 Cu2 N4 N3 28.9(3) 4_656 . . . ?
N4 Cu2 N4 C7 -142.5(4) 4_656 . . . ?
N4 N3 C6 N2 -0.4(5) . . . . ?
N4 N3 C6 C3 178.3(4) . . . . ?
N4 C7 C8 N5 -7.2(7) . . . . ?
N4 C7 C8 N6 172.0(4) . . . . ?
N5 C9 C10 C11 -173.6(5) . . . . ?
N5 C9 C10 C14 7.9(7) . . . . ?
N6 Cu3 N3 N4 -19.3(4) 8_566 . . . ?
N6 Cu3 N3 C6 162.7(4) 8_566 . . . ?
N6 N7 C9 N5 0.9(5) . . . . ?
N6 N7 C9 C10 -178.1(4) . . . . ?
N7 Cu1 N1 C1 177.1(5) 7_655 . . . ?
N7 Cu1 N1 C1 68.4(5) 6_556 . . . ?
N7 Cu1 N1 C5 -3.2(5) 7_655 . . . ?
N7 Cu1 N1 C5 -111.9(4) 6_556 . . . ?
N7 N6 C8 N5 -0.7(5) . . . . ?
N7 N6 C8 C7 -179.9(4) . . . . ?
N7 C9 C10 C11 5.3(8) . . . . ?
N7 C9 C10 C14 -173.1(5) . . . . ?
N8 Cu3 N3 N4 155.3(3) 6_557 . . . ?
N8 Cu3 N3 C6 -22.7(6) 6_557 . . . ?
N8 C13 C14 C10 0.7(8) . . . . ?
C1 N1 C5 C4 -1.8(9) . . . . ?
C1 C2 C3 C4 -1.4(8) . . . . ?
C1 C2 C3 C6 177.7(5) . . . . ?
C2 C3 C4 C5 3.7(9) . . . . ?
C2 C3 C6 N2 7.6(7) . . . . ?
C2 C3 C6 N3 -171.0(5) . . . . ?
C3 C4 C5 N1 -2.2(10) . . . . ?
C4 C3 C6 N2 -173.4(5) . . . . ?
C4 C3 C6 N3 8.0(8) . . . . ?
C5 N1 C1 C2 4.3(9) . . . . ?
C6 N2 C7 N4 -1.0(5) . . . . ?
C6 N2 C7 C8 178.2(4) . . . . ?
C6 N3 N4 Cu2 -173.2(3) . . . . ?
C6 N3 N4 C7 -0.2(5) . . . . ?
C6 C3 C4 C5 -175.4(5) . . . . ?
C7 N2 C6 N3 0.8(5) . . . . ?
C7 N2 C6 C3 -177.9(4) . . . . ?
C8 N5 C9 N7 -1.2(5) . . . . ?
C8 N5 C9 C10 177.8(4) . . . . ?
C8 N6 N7 Cu1 -173.9(3) . . . 6_666 ?
C8 N6 N7 C9 -0.1(4) . . . . ?
C9 N5 C8 N6 1.2(5) . . . . ?
C9 N5 C8 C7 -179.6(4) . . . . ?
C9 C10 C11 C12 -179.1(5) . . . . ?
C9 C10 C14 C13 178.0(5) . . . . ?
C10 C11 C12 N8 1.6(10) . . . . ?
C11 C10 C14 C13 -0.5(8) . . . . ?
C12 N8 C13 C14 0.2(8) . . . . ?
C13 N8 C12 C11 -1.4(9) . . . . ?
C14 C10 C11 C12 -0.6(9) . . . . ?

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1033520'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2014-11-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.25(C56 H48 Mn4 N32 O8), 2(H2 O)'
_chemical_formula_sum            'C14 H16 Mn N8 O4'
_chemical_formula_weight         415.29
_chemical_melting_point          ?
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'
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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+1/4, x+3/4, z+1/4'
3 '-x, -y+1/2, z'
4 'y+1/4, -x+1/4, z+3/4'
5 'x, -y, -z+1/2'
6 '-x+1/2, y, -z'
7 'y+3/4, x+1/4, -z+1/4'
8 '-y+1/4, -x+1/4, -z+1/4'
9 'x+1/2, y+1/2, z+1/2'
10 '-y+3/4, x+5/4, z+3/4'
11 '-x+1/2, -y+1, z+1/2'
12 'y+3/4, -x+3/4, z+5/4'
13 'x+1/2, -y+1/2, -z+1'
14 '-x+1, y+1/2, -z+1/2'
15 'y+5/4, x+3/4, -z+3/4'
16 '-y+3/4, -x+3/4, -z+3/4'
17 '-x, -y, -z'
18 'y-1/4, -x-3/4, -z-1/4'
19 'x, y-1/2, -z'
20 '-y-1/4, x-1/4, -z-3/4'
21 '-x, y, z-1/2'
22 'x-1/2, -y, z'
23 '-y-3/4, -x-1/4, z-1/4'
24 'y-1/4, x-1/4, z-1/4'
25 '-x+1/2, -y+1/2, -z+1/2'
26 'y+1/4, -x-1/4, -z+1/4'
27 'x+1/2, y, -z+1/2'
28 '-y+1/4, x+1/4, -z-1/4'
29 '-x+1/2, y+1/2, z'
30 'x, -y+1/2, z+1/2'
31 '-y-1/4, -x+1/4, z+1/4'
32 'y+1/4, x+1/4, z+1/4'

_cell_length_a                   19.1314(3)
_cell_length_b                   19.1314(3)
_cell_length_c                   20.6667(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7564.2(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.9169
_exptl_absorpt_correction_T_min  0.7524
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9413
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1664
_reflns_number_total             1933
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+12.4393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1180
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.2500 0.10902(3) 0.0000 0.03433(19) Uani 1 2 d S . .
O1 O 0.16612(11) 0.18328(11) 0.00805(9) 0.0569(6) Uani 1 1 d . . .
H1A H 0.1649 0.1995 0.0464 0.085 Uiso 1 1 d R . .
H1B H 0.1276 0.1630 -0.0003 0.085 Uiso 1 1 d R . .
O2 O 0.41143(10) 0.21647(11) 0.10057(9) 0.0523(5) Uani 1 1 d G . .
H2A H 0.3783 0.1990 0.1227 0.078 Uiso 1 1 d G . .
H2B H 0.4001 0.2573 0.0881 0.078 Uiso 1 1 d G . .
N1 N 0.26803(10) 0.11308(11) 0.10997(9) 0.0360(5) Uani 1 1 d . . .
N2 N 0.30129(11) 0.15158(11) 0.15683(9) 0.0393(5) Uani 1 1 d . . .
N3 N 0.22762(10) 0.07744(10) 0.20661(8) 0.0336(4) Uani 1 1 d . . .
N4 N 0.33009(16) 0.22924(14) 0.39028(11) 0.0648(7) Uani 1 1 d . . .
C1 C 0.22576(11) 0.07080(11) 0.14196(10) 0.0308(5) Uani 1 1 d . . .
C2 C 0.27579(13) 0.12931(12) 0.21280(11) 0.0347(5) Uani 1 1 d . . .
C3 C 0.29593(13) 0.16179(13) 0.27475(11) 0.0391(5) Uani 1 1 d . . .
C4 C 0.2629(2) 0.1466(2) 0.33120(14) 0.0749(11) Uani 1 1 d . . .
H4 H 0.2277 0.1130 0.3321 0.090 Uiso 1 1 calc R . .
C5 C 0.2819(2) 0.1813(2) 0.38742(15) 0.0837(12) Uani 1 1 d . . .
H5 H 0.2587 0.1697 0.4255 0.100 Uiso 1 1 calc R . .
C6 C 0.3610(2) 0.2453(2) 0.33518(16) 0.0804(11) Uani 1 1 d . . .
H6 H 0.3947 0.2803 0.3356 0.096 Uiso 1 1 calc R . .
C7 C 0.34633(19) 0.21319(19) 0.27685(15) 0.0704(10) Uani 1 1 d . . .
H7 H 0.3701 0.2261 0.2395 0.084 Uiso 1 1 calc R . .


_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 2.150(2) . ?
Mn1 O1 2.150(2) 6 ?
Mn1 N1 2.3001(18) 6 ?
Mn1 N1 2.3001(18) . ?
Mn1 N3 2.3972(19) 8 ?
Mn1 N3 2.3972(19) 4_554 ?
O1 H1A 0.8518 . ?
O1 H1B 0.8513 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8504 . ?
N1 N2 1.373(3) . ?
N1 C1 1.321(3) . ?
N2 C2 1.326(3) . ?
N3 Mn1 2.3972(19) 2_545 ?
N3 C1 1.343(3) . ?
N3 C2 1.360(3) . ?
N4 C5 1.301(5) . ?
N4 C6 1.319(4) . ?
C1 C1 1.442(4) 8 ?
C2 C3 1.474(3) . ?
C3 C4 1.359(4) . ?
C3 C7 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 97.27(12) . 6 ?
O1 Mn1 N1 86.69(7) . 6 ?
O1 Mn1 N1 90.75(7) 6 6 ?
O1 Mn1 N1 90.75(7) . . ?
O1 Mn1 N1 86.69(7) 6 . ?
O1 Mn1 N3 161.31(6) 6 8 ?
O1 Mn1 N3 88.09(7) . 8 ?
O1 Mn1 N3 88.09(7) 6 4_554 ?
O1 Mn1 N3 161.31(6) . 4_554 ?
N1 Mn1 N1 176.13(10) 6 . ?
N1 Mn1 N3 107.48(7) 6 8 ?
N1 Mn1 N3 75.31(6) . 8 ?
N1 Mn1 N3 75.31(6) 6 4_554 ?
N1 Mn1 N3 107.48(7) . 4_554 ?
N3 Mn1 N3 92.51(9) 8 4_554 ?
Mn1 O1 H1A 109.4 . . ?
Mn1 O1 H1B 109.3 . . ?
H1A O1 H1B 109.4 . . ?
H2A O2 H2B 109.4 . . ?
N2 N1 Mn1 141.68(15) . . ?
C1 N1 Mn1 112.46(14) . . ?
C1 N1 N2 105.02(17) . . ?
C2 N2 N1 105.81(18) . . ?
C1 N3 Mn1 107.19(14) . 2_545 ?
C1 N3 C2 100.40(18) . . ?
C2 N3 Mn1 152.14(14) . 2_545 ?
C5 N4 C6 116.2(3) . . ?
N1 C1 N3 115.08(19) . . ?
N1 C1 C1 120.9(2) . 8 ?
N3 C1 C1 124.0(2) . 8 ?
N2 C2 N3 113.68(19) . . ?
N2 C2 C3 121.7(2) . . ?
N3 C2 C3 124.5(2) . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 C7 116.9(2) . . ?
C7 C3 C2 120.7(2) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
N4 C5 C4 124.2(3) . . ?
N4 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N4 C6 H6 118.0 . . ?
N4 C6 C7 124.0(3) . . ?
C7 C6 H6 118.0 . . ?
C3 C7 C6 119.1(3) . . ?
C3 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?

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
Mn1 N1 N2 C2 167.4(2) . . . . ?
Mn1 N1 C1 N3 -171.85(15) . . . . ?
Mn1 N1 C1 C1 5.09(17) . . . 8 ?
Mn1 N3 C1 N1 176.44(16) 2_545 . . . ?
Mn1 N3 C1 C1 -0.40(16) 2_545 . . 8 ?
Mn1 N3 C2 N2 -172.6(2) 2_545 . . . ?
Mn1 N3 C2 C3 4.0(5) 2_545 . . . ?
O1 Mn1 N1 N2 14.0(3) 6 . . . ?
O1 Mn1 N1 N2 -83.2(3) . . . . ?
O1 Mn1 N1 C1 -178.73(17) 6 . . . ?
O1 Mn1 N1 C1 84.03(17) . . . . ?
N1 Mn1 N1 N2 -34.6(3) 6 . . . ?
N1 Mn1 N1 C1 132.60(16) 6 . . . ?
N1 N2 C2 N3 0.6(3) . . . . ?
N1 N2 C2 C3 -176.1(2) . . . . ?
N2 N1 C1 N3 0.0(3) . . . . ?
N2 N1 C1 C1 176.93(11) . . . 8 ?
N2 C2 C3 C4 170.2(3) . . . . ?
N2 C2 C3 C7 -5.0(4) . . . . ?
N3 Mn1 N1 N2 101.0(3) 4_554 . . . ?
N3 Mn1 N1 N2 -171.0(3) 8 . . . ?
N3 Mn1 N1 C1 -91.78(16) 4_554 . . . ?
N3 Mn1 N1 C1 -3.79(16) 8 . . . ?
N3 C2 C3 C4 -6.1(4) . . . . ?
N3 C2 C3 C7 178.7(3) . . . . ?
N4 C6 C7 C3 0.8(7) . . . . ?
C1 N1 N2 C2 -0.3(3) . . . . ?
C1 N3 C2 N2 -0.6(3) . . . . ?
C1 N3 C2 C3 176.0(2) . . . . ?
C2 N3 C1 N1 0.3(3) . . . . ?
C2 N3 C1 C1 -176.50(12) . . . 8 ?
C2 C3 C4 C5 -176.9(3) . . . . ?
C2 C3 C7 C6 176.3(3) . . . . ?
C3 C4 C5 N4 0.6(7) . . . . ?
C4 C3 C7 C6 0.9(5) . . . . ?
C5 N4 C6 C7 -1.8(6) . . . . ?
C6 N4 C5 C4 1.1(6) . . . . ?
C7 C3 C4 C5 -1.5(6) . . . . ?

