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

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_120521d
_database_code_depnum_ccdc_archive 'CCDC 989725'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N12 O Pb'
_chemical_formula_weight         647.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7700(11)
_cell_length_b                   14.5781(14)
_cell_length_c                   15.7165(18)
_cell_angle_alpha                66.1160(10)
_cell_angle_beta                 71.702(2)
_cell_angle_gamma                68.8200(10)
_cell_volume                     2062.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4451
_cell_measurement_theta_min      2.279
_cell_measurement_theta_max      28.312

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    8.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_T_max  0.23
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10239
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.1103
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.02
_reflns_number_total             7123
_reflns_number_gt                5225
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1996)'
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7123
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.43771(4) 0.60993(3) 0.11176(3) 0.03004(16) Uani 1 1 d . . .
Pb2 Pb 1.01901(4) 0.46716(3) 0.38539(3) 0.02860(16) Uani 1 1 d . . .
N1 N 0.5439(8) 0.8750(7) 0.1338(6) 0.0223(19) Uani 1 1 d . . .
N2 N 0.5366(9) 0.7227(7) 0.1463(7) 0.032(2) Uani 1 1 d . . .
N3 N 0.4297(9) 1.3630(7) 0.0908(7) 0.034(2) Uani 1 1 d . . .
N4 N 0.3454(11) 1.4517(8) 0.1020(7) 0.039(2) Uani 1 1 d . . .
N5 N 0.2208(10) 1.4436(8) 0.1295(7) 0.036(2) Uani 1 1 d . . .
N6 N 0.2192(9) 1.3494(8) 0.1315(7) 0.036(2) Uani 1 1 d . . .
N7 N 0.8192(8) 0.3383(7) 0.1131(6) 0.025(2) Uani 1 1 d . . .
N8 N 0.6671(9) 0.4873(7) 0.1173(7) 0.031(2) Uani 1 1 d . . .
N9 N 1.1691(9) -0.1261(8) 0.1001(7) 0.036(2) Uani 1 1 d . . .
N10 N 1.1811(10) -0.2281(8) 0.1270(7) 0.040(3) Uani 1 1 d . . .
N11 N 1.0631(10) -0.2473(8) 0.1715(7) 0.037(2) Uani 1 1 d . . .
N12 N 0.9691(9) -0.1587(7) 0.1779(7) 0.031(2) Uani 1 1 d . . .
N13 N 0.8965(8) 0.2231(6) 0.3577(6) 0.0214(19) Uani 1 1 d . . .
N14 N 0.9086(9) 0.3721(7) 0.3510(6) 0.030(2) Uani 1 1 d . . .
N15 N 1.2104(10) -0.2500(8) 0.3540(7) 0.041(3) Uani 1 1 d . . .
N16 N 1.2123(11) -0.3489(8) 0.3751(8) 0.049(3) Uani 1 1 d . . .
N17 N 1.0926(11) -0.3639(8) 0.4222(7) 0.042(3) Uani 1 1 d . . .
N18 N 1.0092(9) -0.2737(7) 0.4354(7) 0.035(2) Uani 1 1 d . . .
N19 N 0.6313(8) 0.7354(7) 0.4066(6) 0.024(2) Uani 1 1 d . . .
N20 N 0.7856(9) 0.5843(7) 0.4115(6) 0.029(2) Uani 1 1 d . . .
N21 N 0.4868(9) 1.2325(7) 0.3402(7) 0.031(2) Uani 1 1 d . . .
N22 N 0.3928(9) 1.3248(7) 0.3369(7) 0.033(2) Uani 1 1 d . . .
N23 N 0.2730(9) 1.3142(7) 0.3499(7) 0.036(2) Uani 1 1 d . . .
N24 N 0.2830(9) 1.2153(7) 0.3616(7) 0.029(2) Uani 1 1 d . . .
O1 O 0.4096(9) 0.5261(6) 0.2773(6) 0.057(3) Uani 1 1 d . . .
H1B H 0.3969 0.4667 0.2924 0.069 Uiso 1 1 d R . .
H1C H 0.3423 0.5626 0.3060 0.069 Uiso 1 1 d R . .
O2 O 1.0111(8) 0.5679(6) 0.2219(6) 0.050(2) Uani 1 1 d . . .
H2B H 1.0754 0.5370 0.1868 0.060 Uiso 1 1 d R . .
H2C H 1.0224 0.6270 0.2099 0.060 Uiso 1 1 d R . .
C1 C 0.4985(11) 0.9843(8) 0.1198(7) 0.024(2) Uani 1 1 d . . .
C2 C 0.5842(11) 1.0358(9) 0.1196(8) 0.030(3) Uani 1 1 d . . .
H2 H 0.6741 1.0001 0.1247 0.036 Uiso 1 1 calc R . .
C3 C 0.5376(11) 1.1394(9) 0.1120(8) 0.029(3) Uani 1 1 d . . .
H3 H 0.5969 1.1731 0.1110 0.035 Uiso 1 1 calc R . .
C4 C 0.4035(10) 1.1945(8) 0.1060(7) 0.024(2) Uani 1 1 d . . .
C5 C 0.3178(10) 1.1448(8) 0.1031(7) 0.025(2) Uani 1 1 d . . .
H5 H 0.2284 1.1813 0.0971 0.030 Uiso 1 1 calc R . .
C6 C 0.3649(10) 1.0401(8) 0.1092(7) 0.023(2) Uani 1 1 d . . .
H6 H 0.3073 1.0074 0.1062 0.028 Uiso 1 1 calc R . .
C7 C 0.4752(11) 0.8205(9) 0.1218(8) 0.031(3) Uani 1 1 d . . .
H7 H 0.3947 0.8500 0.0991 0.037 Uiso 1 1 calc R . .
C8 C 0.6543(12) 0.7092(9) 0.1741(8) 0.036(3) Uani 1 1 d . . .
H8 H 0.7199 0.6467 0.1930 0.043 Uiso 1 1 calc R . .
C9 C 0.6557(12) 0.8045(9) 0.1684(8) 0.034(3) Uani 1 1 d . . .
H9 H 0.7206 0.8189 0.1849 0.041 Uiso 1 1 calc R . .
C10 C 0.3510(10) 1.3032(9) 0.1077(7) 0.026(2) Uani 1 1 d . . .
C11 C 0.8734(10) 0.2321(8) 0.1156(7) 0.023(2) Uani 1 1 d . . .
C12 C 0.9870(11) 0.2050(9) 0.0501(8) 0.029(3) Uani 1 1 d . . .
H12 H 1.0275 0.2555 0.0034 0.035 Uiso 1 1 calc R . .
C13 C 1.0407(10) 0.1005(8) 0.0548(7) 0.028(2) Uani 1 1 d . . .
H13 H 1.1180 0.0814 0.0115 0.034 Uiso 1 1 calc R . .
C14 C 0.9787(10) 0.0247(8) 0.1242(7) 0.025(2) Uani 1 1 d . . .
C15 C 0.8617(10) 0.0553(8) 0.1868(7) 0.025(2) Uani 1 1 d . . .
H15 H 0.8184 0.0058 0.2323 0.030 Uiso 1 1 calc R . .
C16 C 0.8088(10) 0.1584(8) 0.1823(7) 0.025(2) Uani 1 1 d . . .
H16 H 0.7296 0.1781 0.2240 0.030 Uiso 1 1 calc R . .
C17 C 0.6872(10) 0.3896(9) 0.1253(8) 0.029(3) Uani 1 1 d . . .
H17 H 0.6175 0.3597 0.1380 0.034 Uiso 1 1 calc R . .
C18 C 0.7965(11) 0.4985(9) 0.0962(8) 0.037(3) Uani 1 1 d . . .
H18 H 0.8161 0.5602 0.0843 0.044 Uiso 1 1 calc R . .
C19 C 0.8892(12) 0.4089(9) 0.0952(8) 0.035(3) Uani 1 1 d . . .
H19 H 0.9829 0.3964 0.0845 0.042 Uiso 1 1 calc R . .
C20 C 1.0376(11) -0.0855(9) 0.1334(8) 0.026(2) Uani 1 1 d . . .
C21 C 0.9404(10) 0.1160(8) 0.3665(7) 0.020(2) Uani 1 1 d . . .
C22 C 1.0590(10) 0.0802(8) 0.3087(7) 0.024(2) Uani 1 1 d . . .
H22 H 1.1070 0.1267 0.2633 0.029 Uiso 1 1 calc R . .
C23 C 1.1068(10) -0.0239(8) 0.3178(7) 0.025(2) Uani 1 1 d . . .
H23 H 1.1874 -0.0470 0.2787 0.030 Uiso 1 1 calc R . .
C24 C 1.0361(10) -0.0961(8) 0.3852(7) 0.024(2) Uani 1 1 d . . .
C25 C 0.9175(10) -0.0573(8) 0.4436(7) 0.025(2) Uani 1 1 d . . .
H25 H 0.8693 -0.1034 0.4895 0.030 Uiso 1 1 calc R . .
C26 C 0.8691(10) 0.0469(8) 0.4357(7) 0.021(2) Uani 1 1 d . . .
H26 H 0.7904 0.0704 0.4759 0.026 Uiso 1 1 calc R . .
C27 C 0.9771(11) 0.2769(9) 0.3551(8) 0.028(2) Uani 1 1 d . . .
H27 H 1.0693 0.2496 0.3561 0.034 Uiso 1 1 calc R . .
C28 C 0.7740(11) 0.3804(9) 0.3528(8) 0.031(3) Uani 1 1 d . . .
H28 H 0.7018 0.4399 0.3514 0.038 Uiso 1 1 calc R . .
C29 C 0.7658(10) 0.2891(8) 0.3569(7) 0.025(2) Uani 1 1 d . . .
H29 H 0.6886 0.2733 0.3588 0.030 Uiso 1 1 calc R . .
C30 C 1.0846(11) -0.2059(9) 0.3926(8) 0.027(2) Uani 1 1 d . . .
C31 C 0.5780(10) 0.8443(8) 0.3916(7) 0.023(2) Uani 1 1 d . . .
C32 C 0.6539(10) 0.8988(8) 0.3985(7) 0.025(2) Uani 1 1 d . . .
H32 H 0.7409 0.8647 0.4113 0.030 Uiso 1 1 calc R . .
C33 C 0.6016(10) 1.0033(8) 0.3865(7) 0.024(2) Uani 1 1 d . . .
H33 H 0.6527 1.0389 0.3928 0.029 Uiso 1 1 calc R . .
C34 C 0.4737(10) 1.0561(8) 0.3653(7) 0.023(2) Uani 1 1 d . . .
C35 C 0.3972(10) 1.0019(8) 0.3586(8) 0.028(2) Uani 1 1 d . . .
H35 H 0.3102 1.0365 0.3460 0.033 Uiso 1 1 calc R . .
C36 C 0.4488(10) 0.8959(8) 0.3706(7) 0.026(2) Uani 1 1 d . . .
H36 H 0.3977 0.8601 0.3646 0.032 Uiso 1 1 calc R . .
C37 C 0.7650(10) 0.6865(9) 0.3825(8) 0.028(2) Uani 1 1 d . . .
H37 H 0.8329 0.7206 0.3498 0.034 Uiso 1 1 calc R . .
C38 C 0.6613(11) 0.5683(9) 0.4575(8) 0.036(3) Uani 1 1 d . . .
H38 H 0.6446 0.5031 0.4874 0.043 Uiso 1 1 calc R . .
C39 C 0.5671(11) 0.6581(8) 0.4538(8) 0.032(3) Uani 1 1 d . . .
H39 H 0.4747 0.6667 0.4787 0.038 Uiso 1 1 calc R . .
C40 C 0.4164(10) 1.1672(8) 0.3561(7) 0.019(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 O1 2.356(8) . ?
Pb1 N8 2.475(9) . ?
Pb1 N2 2.546(9) . ?
Pb2 O2 2.399(8) . ?
Pb2 N14 2.413(9) . ?
Pb2 N20 2.494(9) . ?
N1 C7 1.359(13) . ?
N1 C9 1.367(14) . ?
N1 C1 1.431(14) . ?
N2 C7 1.286(14) . ?
N2 C8 1.391(14) . ?
N3 C10 1.324(13) . ?
N3 N4 1.328(14) . ?
N4 N5 1.308(14) . ?
N5 N6 1.367(13) . ?
N6 C10 1.338(14) . ?
N7 C17 1.340(14) . ?
N7 C19 1.379(13) . ?
N7 C11 1.432(14) . ?
N8 C17 1.320(14) . ?
N8 C18 1.382(13) . ?
N9 N10 1.340(13) . ?
N9 C20 1.345(14) . ?
N10 N11 1.313(13) . ?
N11 N12 1.341(13) . ?
N12 C20 1.347(13) . ?
N13 C27 1.346(13) . ?
N13 C29 1.390(13) . ?
N13 C21 1.419(13) . ?
N14 C27 1.301(14) . ?
N14 C28 1.403(13) . ?
N15 C30 1.336(14) . ?
N15 N16 1.336(14) . ?
N16 N17 1.316(14) . ?
N17 N18 1.353(14) . ?
N18 C30 1.336(13) . ?
N19 C37 1.363(14) . ?
N19 C39 1.366(13) . ?
N19 C31 1.424(13) . ?
N20 C37 1.323(14) . ?
N20 C38 1.361(13) . ?
N21 C40 1.324(13) . ?
N21 N22 1.353(13) . ?
N22 N23 1.297(12) . ?
N23 N24 1.345(13) . ?
N24 C40 1.344(13) . ?
C1 C2 1.383(14) . ?
C1 C6 1.398(14) . ?
C2 C3 1.375(16) . ?
C3 C4 1.388(15) . ?
C4 C5 1.383(14) . ?
C4 C10 1.487(15) . ?
C5 C6 1.396(15) . ?
C8 C9 1.360(16) . ?
C11 C12 1.379(15) . ?
C11 C16 1.381(13) . ?
C12 C13 1.399(15) . ?
C13 C14 1.399(14) . ?
C14 C15 1.387(14) . ?
C14 C20 1.461(15) . ?
C15 C16 1.381(15) . ?
C18 C19 1.329(16) . ?
C21 C22 1.379(15) . ?
C21 C26 1.391(13) . ?
C22 C23 1.377(15) . ?
C23 C24 1.407(13) . ?
C24 C25 1.399(15) . ?
C24 C30 1.460(15) . ?
C25 C26 1.382(14) . ?
C28 C29 1.339(15) . ?
C31 C32 1.381(14) . ?
C31 C36 1.394(14) . ?
C32 C33 1.373(14) . ?
C33 C34 1.384(14) . ?
C34 C35 1.382(14) . ?
C34 C40 1.473(14) . ?
C35 C36 1.393(15) . ?
C38 C39 1.328(16) . ?

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 Pb1 N8 81.6(3) . . ?
O1 Pb1 N2 83.2(3) . . ?
N8 Pb1 N2 84.2(3) . . ?
O2 Pb2 N14 80.5(3) . . ?
O2 Pb2 N20 82.6(3) . . ?
N14 Pb2 N20 84.3(3) . . ?
C7 N1 C9 106.9(9) . . ?
C7 N1 C1 125.1(9) . . ?
C9 N1 C1 127.7(9) . . ?
C7 N2 C8 107.8(10) . . ?
C7 N2 Pb1 115.4(7) . . ?
C8 N2 Pb1 136.1(8) . . ?
C10 N3 N4 105.4(9) . . ?
N5 N4 N3 109.3(9) . . ?
N4 N5 N6 109.9(9) . . ?
C10 N6 N5 102.7(9) . . ?
C17 N7 C19 106.2(9) . . ?
C17 N7 C11 125.7(8) . . ?
C19 N7 C11 128.1(9) . . ?
C17 N8 C18 104.1(9) . . ?
C17 N8 Pb1 120.2(7) . . ?
C18 N8 Pb1 134.5(7) . . ?
N10 N9 C20 104.0(9) . . ?
N11 N10 N9 110.2(9) . . ?
N10 N11 N12 109.8(9) . . ?
N11 N12 C20 104.1(9) . . ?
C27 N13 C29 107.7(9) . . ?
C27 N13 C21 124.2(9) . . ?
C29 N13 C21 127.9(8) . . ?
C27 N14 C28 106.3(9) . . ?
C27 N14 Pb2 115.6(7) . . ?
C28 N14 Pb2 135.3(8) . . ?
C30 N15 N16 104.5(9) . . ?
N17 N16 N15 110.5(10) . . ?
N16 N17 N18 108.4(9) . . ?
C30 N18 N17 104.9(9) . . ?
C37 N19 C39 105.7(9) . . ?
C37 N19 C31 124.9(9) . . ?
C39 N19 C31 129.2(9) . . ?
C37 N20 C38 104.9(9) . . ?
C37 N20 Pb2 120.8(7) . . ?
C38 N20 Pb2 134.2(7) . . ?
C40 N21 N22 104.7(8) . . ?
N23 N22 N21 109.6(8) . . ?
N22 N23 N24 109.7(9) . . ?
C40 N24 N23 104.5(8) . . ?
C2 C1 C6 118.9(10) . . ?
C2 C1 N1 120.7(9) . . ?
C6 C1 N1 120.3(9) . . ?
C3 C2 C1 120.5(10) . . ?
C2 C3 C4 121.2(10) . . ?
C5 C4 C3 118.8(10) . . ?
C5 C4 C10 120.6(9) . . ?
C3 C4 C10 120.5(9) . . ?
C4 C5 C6 120.3(10) . . ?
C5 C6 C1 120.1(9) . . ?
N2 C7 N1 110.8(10) . . ?
C9 C8 N2 107.3(10) . . ?
C8 C9 N1 107.2(10) . . ?
N3 C10 N6 112.6(10) . . ?
N3 C10 C4 123.8(9) . . ?
N6 C10 C4 123.5(9) . . ?
C12 C11 C16 120.7(10) . . ?
C12 C11 N7 119.8(9) . . ?
C16 C11 N7 119.4(9) . . ?
C11 C12 C13 119.2(10) . . ?
C14 C13 C12 120.4(10) . . ?
C15 C14 C13 118.8(10) . . ?
C15 C14 C20 120.0(9) . . ?
C13 C14 C20 121.1(9) . . ?
C16 C15 C14 120.8(9) . . ?
C11 C16 C15 120.0(9) . . ?
N8 C17 N7 112.4(9) . . ?
C19 C18 N8 110.7(10) . . ?
C18 C19 N7 106.6(10) . . ?
N9 C20 N12 111.9(10) . . ?
N9 C20 C14 123.4(9) . . ?
N12 C20 C14 124.7(10) . . ?
C22 C21 C26 120.3(10) . . ?
C22 C21 N13 119.0(9) . . ?
C26 C21 N13 120.6(9) . . ?
C23 C22 C21 120.4(9) . . ?
C22 C23 C24 121.2(10) . . ?
C25 C24 C23 116.8(10) . . ?
C25 C24 C30 122.1(9) . . ?
C23 C24 C30 121.1(10) . . ?
C26 C25 C24 122.5(9) . . ?
C25 C26 C21 118.8(9) . . ?
N14 C27 N13 110.9(9) . . ?
C29 C28 N14 109.3(10) . . ?
C28 C29 N13 105.8(9) . . ?
N15 C30 N18 111.7(10) . . ?
N15 C30 C24 123.4(9) . . ?
N18 C30 C24 124.9(10) . . ?
C32 C31 C36 119.8(10) . . ?
C32 C31 N19 120.0(9) . . ?
C36 C31 N19 120.1(9) . . ?
C33 C32 C31 120.3(9) . . ?
C32 C33 C34 120.8(10) . . ?
C35 C34 C33 119.2(10) . . ?
C35 C34 C40 120.3(9) . . ?
C33 C34 C40 120.4(9) . . ?
C34 C35 C36 120.7(10) . . ?
C35 C36 C31 119.2(10) . . ?
N20 C37 N19 111.2(9) . . ?
C39 C38 N20 110.9(10) . . ?
C38 C39 N19 107.2(9) . . ?
N21 C40 N24 111.5(9) . . ?
N21 C40 C34 125.6(9) . . ?
N24 C40 C34 123.0(9) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         2.606
_refine_diff_density_min         -3.310
_refine_diff_density_rms         0.273
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_120614g
_database_code_depnum_ccdc_archive 'CCDC 989726'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N12 Ni O6'
_chemical_formula_weight         589.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.2296(18)
_cell_length_b                   13.2582(12)
_cell_length_c                   13.4958(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.226(2)
_cell_angle_gamma                90.00
_cell_volume                     2665.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    898
_cell_measurement_theta_min      3.104
_cell_measurement_theta_max      20.480

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6623
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_sigmaI/netI    0.1235
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2342
_reflns_number_gt                1303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1996)'
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2342
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.85511(7) 0.7500 0.0388(3) Uani 1 2 d S . .
N1 N 0.586(3) 0.687(5) 0.573(5) 0.043(6) Uani 0.719(11) 1 d P A 1
N2 N 0.531(13) 0.746(14) 0.672(9) 0.040(10) Uani 0.719(11) 1 d P A 1
N1' N 0.569(9) 0.685(14) 0.552(14) 0.043(6) Uani 0.281(11) 1 d P A 2
N2' N 0.52(3) 0.74(4) 0.65(2) 0.04(3) Uani 0.281(11) 1 d P A 2
N3 N 0.7278(3) 0.6114(3) 0.2386(4) 0.0454(11) Uani 1 1 d . A .
N4 N 0.7366(3) 0.6458(3) 0.1516(4) 0.0452(11) Uani 1 1 d . . .
N5 N 0.7029(3) 0.7384(3) 0.1141(4) 0.0470(11) Uani 1 1 d . . .
N6 N 0.6705(3) 0.7676(3) 0.1748(4) 0.0464(11) Uani 1 1 d . A .
O1 O 0.4945(2) 0.9729(2) 0.8502(3) 0.0477(10) Uani 1 1 d . A .
H1C H 0.5405 0.9703 0.9288 0.057 Uiso 1 1 d R . .
H1D H 0.4498 0.9895 0.8453 0.057 Uiso 1 1 d R . .
O2 O 0.6389(2) 0.8687(2) 0.9030(3) 0.0452(9) Uani 1 1 d . A .
H2C H 0.6751 0.8649 0.8870 0.054 Uiso 1 1 d R . .
H2D H 0.6577 0.8300 0.9657 0.054 Uiso 1 1 d R . .
O3 O 0.6289(2) 0.9734(2) 0.1208(3) 0.0495(10) Uani 1 1 d . . .
H3C H 0.6457 0.9124 0.1412 0.059 Uiso 1 1 d R . .
H3D H 0.6749 1.0112 0.1660 0.059 Uiso 1 1 d R . .
C1 C 0.5464(4) 0.7652(4) 0.5873(5) 0.0477(14) Uani 1 1 d . . .
H1 H 0.5309 0.8258 0.5431 0.057 Uiso 1 1 calc R A 1
C2 C 0.5750(6) 0.6545(6) 0.7235(9) 0.047(3) Uani 0.719(11) 1 d P A 1
H2 H 0.5811 0.6219 0.7895 0.057 Uiso 0.719(11) 1 calc PR A 1
C3 C 0.6084(6) 0.6177(5) 0.6656(8) 0.047(3) Uani 0.719(11) 1 d P A 1
H3 H 0.6397 0.5578 0.6847 0.057 Uiso 0.719(11) 1 calc PR A 1
C2' C 0.4958(17) 0.6433(15) 0.622(2) 0.047(7) Uani 0.281(11) 1 d P A 2
H2' H 0.4653 0.6076 0.6434 0.057 Uiso 0.281(11) 1 calc PR A 2
C3' C 0.5257(16) 0.6065(14) 0.560(2) 0.047(7) Uani 0.281(11) 1 d P A 2
H3' H 0.5185 0.5412 0.5297 0.057 Uiso 0.281(11) 1 calc PR A 2
C4 C 0.6077(3) 0.6866(4) 0.4874(5) 0.0401(13) Uani 1 1 d . . .
C5 C 0.6005(4) 0.7735(4) 0.4238(5) 0.0490(14) Uani 1 1 d . A .
H5 H 0.5783 0.8323 0.4323 0.059 Uiso 1 1 calc R . .
C6 C 0.6260(4) 0.7738(4) 0.3475(5) 0.0491(14) Uani 1 1 d . . .
H6 H 0.6198 0.8325 0.3048 0.059 Uiso 1 1 calc R A .
C7 C 0.6608(3) 0.6868(4) 0.3340(5) 0.0362(12) Uani 1 1 d . A .
C8 C 0.6687(4) 0.5995(4) 0.4003(5) 0.0471(14) Uani 1 1 d . . .
H8 H 0.6918 0.5408 0.3931 0.057 Uiso 1 1 calc R A .
C9 C 0.6426(4) 0.5988(4) 0.4765(5) 0.0509(15) Uani 1 1 d . A .
H9 H 0.6485 0.5404 0.5194 0.061 Uiso 1 1 calc R . .
C10 C 0.6868(3) 0.6878(4) 0.2507(4) 0.0375(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 2.09(17) . ?
Ni1 N2 2.09(17) 2_656 ?
Ni1 O2 2.111(3) . ?
Ni1 O2 2.111(3) 2_656 ?
Ni1 O1 2.111(3) . ?
Ni1 O1 2.111(3) 2_656 ?
Ni1 N2' 2.2(4) . ?
Ni1 N2' 2.2(4) 2_656 ?
N1 C1 1.37(7) . ?
N1 C3 1.38(7) . ?
N1 C4 1.46(7) . ?
N2 C1 1.36(14) . ?
N2 C2 1.39(19) . ?
N1' C1 1.34(18) . ?
N1' C3' 1.38(18) . ?
N1' C4 1.47(17) . ?
N2' C1 1.2(4) . ?
N2' C2' 1.4(5) . ?
N3 C10 1.356(6) . ?
N3 N4 1.367(5) . ?
N4 N5 1.329(5) . ?
N5 N6 1.361(5) . ?
N6 C10 1.365(6) . ?
C2 C3 1.376(9) . ?
C2' C3' 1.37(2) . ?
C4 C5 1.390(6) . ?
C4 C9 1.398(6) . ?
C5 C6 1.394(6) . ?
C6 C7 1.402(6) . ?
C7 C8 1.412(6) . ?
C7 C10 1.491(6) . ?
C8 C9 1.400(6) . ?

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
N2 Ni1 N2 93(10) . 2_656 ?
N2 Ni1 O2 88(5) . . ?
N2 Ni1 O2 99(5) 2_656 . ?
N2 Ni1 O2 99(5) . 2_656 ?
N2 Ni1 O2 88(5) 2_656 2_656 ?
O2 Ni1 O2 170.20(18) . 2_656 ?
N2 Ni1 O1 169(5) . . ?
N2 Ni1 O1 92(5) 2_656 . ?
O2 Ni1 O1 81.68(13) . . ?
O2 Ni1 O1 91.06(13) 2_656 . ?
N2 Ni1 O1 92(5) . 2_656 ?
N2 Ni1 O1 169(5) 2_656 2_656 ?
O2 Ni1 O1 91.06(13) . 2_656 ?
O2 Ni1 O1 81.68(13) 2_656 2_656 ?
O1 Ni1 O1 84.58(17) . 2_656 ?
N2 Ni1 N2' 6(10) . . ?
N2 Ni1 N2' 95(7) 2_656 . ?
O2 Ni1 N2' 93(10) . . ?
O2 Ni1 N2' 93(10) 2_656 . ?
O1 Ni1 N2' 172(10) . . ?
O1 Ni1 N2' 89(10) 2_656 . ?
N2 Ni1 N2' 95(7) . 2_656 ?
N2 Ni1 N2' 6(10) 2_656 2_656 ?
O2 Ni1 N2' 93(10) . 2_656 ?
O2 Ni1 N2' 93(10) 2_656 2_656 ?
O1 Ni1 N2' 89(10) . 2_656 ?
O1 Ni1 N2' 172(10) 2_656 2_656 ?
C1 N1 C3 105(4) . . ?
C1 N1 C4 125(5) . . ?
C3 N1 C4 129(5) . . ?
C1 N2 C2 102(10) . . ?
C1 N2 Ni1 125(10) . . ?
C2 N2 Ni1 129(6) . . ?
C1 N1' C3' 103(10) . . ?
C1 N1' C4 127(10) . . ?
C3' N1' C4 128(10) . . ?
C1 N2' C2' 106(10) . . ?
C10 N3 N4 104.6(4) . . ?
N5 N4 N3 109.8(4) . . ?
N4 N5 N6 109.4(4) . . ?
N5 N6 C10 104.8(4) . . ?
N2' C1 N1' 114(10) . . ?
N2' C1 N2 10(10) . . ?
N1' C1 N2 116(10) . . ?
N2' C1 N1 115(10) . . ?
N1' C1 N1 12(7) . . ?
N2 C1 N1 114(9) . . ?
C3 C2 N2 112(6) . . ?
C2 C3 N1 107(3) . . ?
C3' C2' N2' 106(10) . . ?
C2' C3' N1' 107(8) . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 N1 121(3) . . ?
C9 C4 N1 119(3) . . ?
C5 C4 N1' 119(7) . . ?
C9 C4 N1' 121(7) . . ?
N1 C4 N1' 11(7) . . ?
C4 C5 C6 120.9(5) . . ?
C5 C6 C7 120.9(5) . . ?
C6 C7 C8 117.5(4) . . ?
C6 C7 C10 120.4(4) . . ?
C8 C7 C10 122.1(4) . . ?
C9 C8 C7 121.7(5) . . ?
C4 C9 C8 119.4(5) . . ?
N3 C10 N6 111.3(4) . . ?
N3 C10 C7 125.6(4) . . ?
N6 C10 C7 123.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_120629c
_database_code_depnum_ccdc_archive 'CCDC 989727'
_audit_update_record             
;
2014-03-03 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Co N12 O6'
_chemical_formula_weight         589.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.96(4)
_cell_length_b                   12.97(4)
_cell_length_c                   13.27(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.51(5)
_cell_angle_gamma                90.00
_cell_volume                     2518(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      3.075
_cell_measurement_theta_max      26.616

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1220
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5659
_diffrn_reflns_av_R_equivalents  0.1583
_diffrn_reflns_av_sigmaI/netI    0.1568
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2214
_reflns_number_gt                1150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1996)'
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1746P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     196
_refine_ls_number_restraints     516
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2970
_refine_ls_wR_factor_gt          0.2251
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.0000 0.14630(10) 0.7500 0.0350(5) Uani 1 2 d SU . .
N1 N 0.0816(4) 0.3154(5) 0.5657(6) 0.0416(14) Uani 1 1 d U . .
N2 N 0.0292(4) 0.2580(5) 0.6632(6) 0.0428(14) Uani 1 1 d U . .
N3 N 0.1710(4) 0.2310(5) 0.1761(5) 0.0421(14) Uani 1 1 d U . .
N4 N 0.2032(4) 0.2600(5) 0.1156(5) 0.0452(15) Uani 1 1 d U . .
N5 N 0.2369(5) 0.3517(5) 0.1513(6) 0.0471(15) Uani 1 1 d U . .
N6 N 0.2270(4) 0.3869(5) 0.2386(6) 0.0447(15) Uani 1 1 d U . .
O1 O -0.1413(3) 0.1326(4) 0.5972(4) 0.0419(13) Uani 1 1 d U . .
H1C H -0.1605 0.1713 0.5326 0.050 Uiso 1 1 d R A .
H1D H -0.1782 0.1373 0.6131 0.050 Uiso 1 1 d R . .
O2 O 0.0047(3) 0.0279(4) 0.6464(4) 0.0450(13) Uani 1 1 d U . .
H2C H 0.0504 0.0109 0.6519 0.054 Uiso 1 1 d R A .
H2D H -0.0422 0.0300 0.5660 0.054 Uiso 1 1 d R . .
O3 O 0.1301(3) 0.9736(4) 0.6227(4) 0.0438(13) Uani 1 1 d . . .
H3C H 0.1473 0.9112 0.6438 0.053 Uiso 1 1 d R . .
H3D H 0.1770 1.0122 0.6682 0.053 Uiso 1 1 d R . .
C1 C 0.1095(5) 0.3147(5) 0.4872(6) 0.0337(14) Uani 1 1 d U A .
C2 C 0.0987(5) 0.2276(6) 0.4230(7) 0.0451(17) Uani 1 1 d U . .
H2 H 0.0737 0.1690 0.4298 0.054 Uiso 1 1 calc R A .
C3 C 0.1256(5) 0.2262(6) 0.3462(7) 0.0432(16) Uani 1 1 d U A .
H3 H 0.1194 0.1661 0.3029 0.052 Uiso 1 1 calc R . .
C4 C 0.1609(5) 0.3131(5) 0.3344(6) 0.0339(14) Uani 1 1 d U . .
C5 C 0.1702(5) 0.4004(6) 0.4003(7) 0.0446(17) Uani 1 1 d U A .
H5 H 0.1953 0.4594 0.3944 0.054 Uiso 1 1 calc R . .
C6 C 0.1430(5) 0.4023(6) 0.4750(7) 0.0431(16) Uani 1 1 d U . .
H6 H 0.1475 0.4626 0.5166 0.052 Uiso 1 1 calc R A .
C7 C 0.0468(5) 0.2367(6) 0.5851(7) 0.0480(17) Uani 1 1 d U A .
H7 H 0.0361 0.1723 0.5467 0.058 Uiso 1 1 calc R . .
C8 C 0.0756(8) 0.3474(8) 0.7201(11) 0.051(3) Uani 0.717(10) 1 d PU A 1
H8 H 0.0844 0.3784 0.7905 0.061 Uiso 0.717(10) 1 calc PR A 1
C9 C 0.1070(8) 0.3848(9) 0.6614(11) 0.050(2) Uani 0.717(10) 1 d PU A 1
H9 H 0.1395 0.4457 0.6815 0.060 Uiso 0.717(10) 1 calc PR A 1
C8' C 0.000(2) 0.364(2) 0.628(3) 0.050(5) Uani 0.283(10) 1 d PU A 2
H8' H -0.0315 0.4025 0.6474 0.060 Uiso 0.283(10) 1 calc PR A 2
C9' C 0.029(2) 0.397(2) 0.562(3) 0.053(5) Uani 0.283(10) 1 d PU A 2
H9' H 0.0171 0.4609 0.5219 0.064 Uiso 0.283(10) 1 calc PR A 2
C10 C 0.1877(5) 0.3109(5) 0.2517(6) 0.0350(15) Uani 1 1 d U A .


_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 2.100(7) . ?
Co1 O1 2.100(7) 2_556 ?
Co1 O2 2.101(6) 2_556 ?
Co1 O2 2.101(6) . ?
Co1 N2 2.132(7) 2_556 ?
Co1 N2 2.132(7) . ?
N1 C7 1.326(9) . ?
N1 C9 1.370(13) . ?
N1 C9' 1.43(3) . ?
N1 C1 1.438(8) . ?
N2 C7 1.304(9) . ?
N2 C8 1.358(12) . ?
N2 C8' 1.45(3) . ?
N3 C10 1.331(9) . ?
N3 N4 1.336(8) . ?
N4 N5 1.288(9) . ?
N5 N6 1.365(9) . ?
N6 C10 1.311(9) . ?
O1 H1C 0.8500 . ?
O1 H1D 0.8500 . ?
O2 H2C 0.8499 . ?
O2 H2D 0.8501 . ?
O3 H3C 0.8500 . ?
O3 H3D 0.8500 . ?
C1 C2 1.349(10) . ?
C1 C6 1.361(10) . ?
C2 C3 1.400(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(11) . ?
C4 C10 1.474(9) . ?
C5 C6 1.379(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.335(15) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C8' C9' 1.37(4) . ?
C8' H8' 0.9300 . ?
C9' H9' 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 170.3(3) . 2_556 ?
O1 Co1 O2 90.6(2) . 2_556 ?
O1 Co1 O2 82.3(2) 2_556 2_556 ?
O1 Co1 O2 82.3(2) . . ?
O1 Co1 O2 90.6(2) 2_556 . ?
O2 Co1 O2 86.0(4) 2_556 . ?
O1 Co1 N2 88.2(3) . 2_556 ?
O1 Co1 N2 98.4(3) 2_556 2_556 ?
O2 Co1 N2 90.5(3) 2_556 2_556 ?
O2 Co1 N2 169.9(2) . 2_556 ?
O1 Co1 N2 98.4(3) . . ?
O1 Co1 N2 88.2(3) 2_556 . ?
O2 Co1 N2 169.9(2) 2_556 . ?
O2 Co1 N2 90.5(3) . . ?
N2 Co1 N2 94.4(4) 2_556 . ?
C7 N1 C9 104.6(7) . . ?
C7 N1 C9' 99.1(13) . . ?
C9 N1 C9' 51.1(12) . . ?
C7 N1 C1 126.4(6) . . ?
C9 N1 C1 127.0(7) . . ?
C9' N1 C1 123.2(13) . . ?
C7 N2 C8 102.7(7) . . ?
C7 N2 C8' 100.7(13) . . ?
C8 N2 C8' 49.0(12) . . ?
C7 N2 Co1 124.8(5) . . ?
C8 N2 Co1 125.4(6) . . ?
C8' N2 Co1 130.1(13) . . ?
C10 N3 N4 104.6(6) . . ?
N5 N4 N3 110.4(6) . . ?
N4 N5 N6 108.5(6) . . ?
C10 N6 N5 104.9(6) . . ?
Co1 O1 H1C 112.8 . . ?
Co1 O1 H1D 120.0 . . ?
H1C O1 H1D 108.4 . . ?
Co1 O2 H2C 126.8 . . ?
Co1 O2 H2D 110.6 . . ?
H2C O2 H2D 108.1 . . ?
H3C O3 H3D 108.5 . . ?
C2 C1 C6 121.2(6) . . ?
C2 C1 N1 119.0(6) . . ?
C6 C1 N1 119.7(6) . . ?
C1 C2 C3 119.4(7) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 118.7(6) . . ?
C3 C4 C10 119.6(6) . . ?
C5 C4 C10 121.7(6) . . ?
C4 C5 C6 121.2(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.1(7) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C7 N1 113.6(7) . . ?
N2 C7 H7 123.2 . . ?
N1 C7 H7 123.2 . . ?
C9 C8 N2 111.0(9) . . ?
C9 C8 H8 124.5 . . ?
N2 C8 H8 124.5 . . ?
C8 C9 N1 106.1(9) . . ?
C8 C9 H9 127.0 . . ?
N1 C9 H9 127.0 . . ?
C9' C8' N2 106(2) . . ?
C9' C8' H8' 127.0 . . ?
N2 C8' H8' 127.0 . . ?
C8' C9' N1 107(2) . . ?
C8' C9' H9' 126.3 . . ?
N1 C9' H9' 126.3 . . ?
N6 C10 N3 111.6(6) . . ?
N6 C10 C4 125.2(6) . . ?
N3 C10 C4 123.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.170
_refine_diff_density_min         -1.377
_refine_diff_density_rms         0.177

#===END
