# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_160326e
_database_code_depnum_ccdc_archive 'CCDC 1533555'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N2 O10 Zn'
_chemical_formula_weight         562.80

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'
Zn Zn 0.2839 1.4301 '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                   21.9751(19)
_cell_length_b                   7.6630(7)
_cell_length_c                   29.079(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.209(2)
_cell_angle_gamma                90.00
_cell_volume                     4786.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2250
_cell_measurement_theta_min      2.608
_cell_measurement_theta_max      21.896

_exptl_crystal_description       tufted
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2312
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11599
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4214
_reflns_number_gt                2658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+1.7040P] 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         4214
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.14337(2) 0.81958(7) 0.198370(18) 0.03388(19) Uani 1 1 d U . .
N1 N 0.06825(15) 0.9374(5) 0.15662(12) 0.0351(10) Uani 1 1 d . . .
N2 N -0.10006(16) 1.1339(5) 0.07899(13) 0.0418(11) Uani 1 1 d . . .
H2 H -0.1260 1.1628 0.0961 0.050 Uiso 1 1 calc R . .
O1 O 0.39037(15) 0.2886(5) 0.24457(11) 0.0479(9) Uani 1 1 d . . .
O2 O 0.31724(14) 0.0925(5) 0.21851(11) 0.0509(10) Uani 1 1 d . . .
O3 O 0.43060(15) 0.0841(6) 0.01190(12) 0.0686(13) Uani 1 1 d . . .
H3 H 0.4496 0.0589 -0.0086 0.103 Uiso 1 1 calc R . .
O4 O 0.51842(15) -0.0032(6) 0.05744(11) 0.0691(13) Uani 1 1 d . . .
O5 O 0.21032(18) 0.6888(5) 0.16822(13) 0.0608(11) Uani 1 1 d . . .
O6 O 0.12514(15) 0.5504(5) 0.16854(13) 0.0597(10) Uani 1 1 d U . .
O7 O -0.08779(16) 1.1331(5) 0.00336(12) 0.0596(11) Uani 1 1 d . . .
O8 O 0.19840(14) 1.0178(5) 0.22053(14) 0.0747(13) Uani 1 1 d . . .
H8C H 0.2354 1.0501 0.2204 0.090 Uiso 1 1 d R . .
H8D H 0.1778 1.1063 0.2261 0.090 Uiso 1 1 d R . .
O9 O 0.32747(16) 0.7661(5) 0.14818(13) 0.0666(11) Uani 1 1 d . . .
H9C H 0.2925 0.7227 0.1499 0.080 Uiso 1 1 d R . .
H9D H 0.3331 0.8572 0.1652 0.080 Uiso 1 1 d R . .
O10 O 0.1255(2) 0.2741(6) 0.23820(17) 0.0962(16) Uani 1 1 d . . .
H10C H 0.1193 0.3271 0.2119 0.115 Uiso 1 1 d R . .
H10D H 0.1435 0.3449 0.2592 0.115 Uiso 1 1 d R . .
C1 C 0.3616(2) 0.1853(7) 0.21409(15) 0.0313(11) Uani 1 1 d . . .
C2 C 0.4647(2) 0.0538(7) 0.05200(17) 0.0425(13) Uani 1 1 d . . .
C3 C 0.38704(18) 0.1639(6) 0.17048(14) 0.0282(10) Uani 1 1 d . . .
C4 C 0.34962(18) 0.1802(6) 0.12513(14) 0.0258(10) Uani 1 1 d . . .
C5 C 0.37611(19) 0.1463(6) 0.08708(15) 0.0326(11) Uani 1 1 d . . .
H5 H 0.3523 0.1605 0.0568 0.039 Uiso 1 1 calc R . .
C6 C 0.43735(19) 0.0917(6) 0.09284(15) 0.0331(11) Uani 1 1 d . . .
C7 C 0.47390(19) 0.0743(7) 0.13785(16) 0.0400(12) Uani 1 1 d . . .
H7 H 0.5148 0.0356 0.1420 0.048 Uiso 1 1 calc R . .
C8 C 0.44929(19) 0.1144(6) 0.17579(16) 0.0365(12) Uani 1 1 d . . .
H8 H 0.4744 0.1087 0.2058 0.044 Uiso 1 1 calc R . .
C9 C 0.1778(2) 0.5577(8) 0.15822(16) 0.0435(13) Uani 1 1 d . . .
C10 C 0.1994(2) 0.4085(6) 0.13316(15) 0.0356(12) Uani 1 1 d . . .
C11 C 0.26219(19) 0.3665(6) 0.14082(14) 0.0294(11) Uani 1 1 d . . .
H11 H 0.2909 0.4308 0.1623 0.035 Uiso 1 1 calc R . .
C12 C 0.28253(18) 0.2297(6) 0.11682(14) 0.0255(10) Uani 1 1 d . . .
C13 C 0.2386(2) 0.1369(6) 0.08414(16) 0.0373(12) Uani 1 1 d . . .
H13 H 0.2516 0.0462 0.0673 0.045 Uiso 1 1 calc R . .
C14 C 0.1763(2) 0.1782(7) 0.07663(17) 0.0459(14) Uani 1 1 d . . .
H14 H 0.1475 0.1162 0.0546 0.055 Uiso 1 1 calc R . .
C15 C 0.1570(2) 0.3102(7) 0.10160(17) 0.0447(13) Uani 1 1 d . . .
H15 H 0.1147 0.3345 0.0973 0.054 Uiso 1 1 calc R . .
C16 C 0.0559(2) 0.9352(7) 0.10981(17) 0.0420(13) Uani 1 1 d . . .
H16 H 0.0855 0.8857 0.0952 0.050 Uiso 1 1 calc R . .
C17 C 0.0026(2) 1.0008(7) 0.08140(16) 0.0453(14) Uani 1 1 d . . .
H17 H -0.0031 0.9974 0.0488 0.054 Uiso 1 1 calc R . .
C18 C -0.0422(2) 1.0721(7) 0.10299(16) 0.0382(12) Uani 1 1 d . . .
C19 C -0.0301(2) 1.0761(7) 0.15185(16) 0.0434(13) Uani 1 1 d . . .
H19 H -0.0590 1.1237 0.1675 0.052 Uiso 1 1 calc R . .
C20 C 0.0249(2) 1.0091(7) 0.17679(16) 0.0426(13) Uani 1 1 d . . .
H20 H 0.0324 1.0137 0.2095 0.051 Uiso 1 1 calc R . .
C21 C -0.1202(2) 1.1537(7) 0.03134(18) 0.0422(13) Uani 1 1 d . . .
C22 C -0.1882(2) 1.2059(6) 0.01644(15) 0.0360(12) Uani 1 1 d . . .
C23 C -0.2335(2) 1.1400(7) 0.03776(16) 0.0442(14) Uani 1 1 d . . .
H23 H -0.2224 1.0648 0.0633 0.053 Uiso 1 1 calc R . .
C24 C -0.2051(2) 1.3161(7) -0.02190(16) 0.0438(13) Uani 1 1 d . . .
H24 H -0.1749 1.3602 -0.0368 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
Zn1 O8 1.964(4) . ?
Zn1 O1 1.970(3) 4 ?
Zn1 N1 2.041(3) . ?
Zn1 O5 2.117(3) . ?
Zn1 O6 2.241(4) . ?
N1 C16 1.331(6) . ?
N1 C20 1.339(5) . ?
N2 C21 1.371(6) . ?
N2 C18 1.397(5) . ?
N2 H2 0.8600 . ?
O1 C1 1.255(5) . ?
O1 Zn1 1.970(3) 4_545 ?
O2 C1 1.235(5) . ?
O3 C2 1.267(5) . ?
O3 H3 0.8200 . ?
O4 C2 1.236(5) . ?
O5 C9 1.232(6) . ?
O6 C9 1.256(5) . ?
O7 C21 1.200(5) . ?
O8 H8C 0.8500 . ?
O8 H8D 0.8499 . ?
O9 H9C 0.8498 . ?
O9 H9D 0.8499 . ?
O10 H10C 0.8500 . ?
O10 H10D 0.8501 . ?
C1 C3 1.500(6) . ?
C2 C6 1.469(6) . ?
C3 C8 1.396(5) . ?
C3 C4 1.404(6) . ?
C4 C5 1.379(6) . ?
C4 C12 1.492(5) . ?
C5 C6 1.385(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(6) . ?
C7 C8 1.363(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.486(7) . ?
C10 C15 1.384(6) . ?
C10 C11 1.389(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(6) . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(6) . ?
C19 C20 1.370(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.518(6) . ?
C22 C23 1.375(6) . ?
C22 C24 1.385(6) . ?
C23 C24 1.372(6) 7_475 ?
C23 H23 0.9300 . ?
C24 C23 1.372(6) 7_475 ?
C24 H24 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
O8 Zn1 O1 97.61(15) . 4 ?
O8 Zn1 N1 102.56(17) . . ?
O1 Zn1 N1 98.82(14) 4 . ?
O8 Zn1 O5 93.93(16) . . ?
O1 Zn1 O5 135.23(15) 4 . ?
N1 Zn1 O5 120.56(15) . . ?
O8 Zn1 O6 152.43(14) . . ?
O1 Zn1 O6 98.44(15) 4 . ?
N1 Zn1 O6 96.95(14) . . ?
O5 Zn1 O6 59.13(14) . . ?
C16 N1 C20 116.4(4) . . ?
C16 N1 Zn1 124.5(3) . . ?
C20 N1 Zn1 118.8(3) . . ?
C21 N2 C18 127.5(4) . . ?
C21 N2 H2 116.3 . . ?
C18 N2 H2 116.3 . . ?
C1 O1 Zn1 116.6(3) . 4_545 ?
C2 O3 H3 109.5 . . ?
C9 O5 Zn1 93.7(3) . . ?
C9 O6 Zn1 87.3(3) . . ?
Zn1 O8 H8C 138.3 . . ?
Zn1 O8 H8D 111.3 . . ?
H8C O8 H8D 108.5 . . ?
H9C O9 H9D 107.9 . . ?
H10C O10 H10D 107.7 . . ?
O2 C1 O1 125.5(4) . . ?
O2 C1 C3 117.9(4) . . ?
O1 C1 C3 116.3(4) . . ?
O4 C2 O3 123.1(4) . . ?
O4 C2 C6 120.6(4) . . ?
O3 C2 C6 116.3(4) . . ?
C8 C3 C4 119.6(4) . . ?
C8 C3 C1 117.9(4) . . ?
C4 C3 C1 122.4(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C12 119.2(4) . . ?
C3 C4 C12 122.5(4) . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 C2 121.0(4) . . ?
C7 C6 C2 119.2(4) . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C3 121.3(4) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
O5 C9 O6 119.8(5) . . ?
O5 C9 C10 120.9(5) . . ?
O6 C9 C10 119.3(5) . . ?
C15 C10 C11 119.1(4) . . ?
C15 C10 C9 120.3(4) . . ?
C11 C10 C9 120.6(4) . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 C4 121.6(4) . . ?
C13 C12 C4 119.9(4) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
N1 C16 C17 124.9(4) . . ?
N1 C16 H16 117.6 . . ?
C17 C16 H16 117.6 . . ?
C16 C17 C18 117.9(4) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C17 C18 C19 118.1(4) . . ?
C17 C18 N2 124.4(4) . . ?
C19 C18 N2 117.4(4) . . ?
C20 C19 C18 119.3(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N1 C20 C19 123.5(4) . . ?
N1 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
O7 C21 N2 124.0(4) . . ?
O7 C21 C22 122.1(4) . . ?
N2 C21 C22 114.0(4) . . ?
C23 C22 C24 119.4(4) . . ?
C23 C22 C21 122.5(4) . . ?
C24 C22 C21 118.1(4) . . ?
C24 C23 C22 120.8(4) 7_475 . ?
C24 C23 H23 119.6 7_475 . ?
C22 C23 H23 119.6 . . ?
C23 C24 C22 119.8(4) 7_475 . ?
C23 C24 H24 120.1 7_475 . ?
C22 C24 H24 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_160329f
_database_code_depnum_ccdc_archive 'CCDC 1533557'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H64 Co3 N8 O27'
_chemical_formula_weight         1578.04

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.4462(7)
_cell_length_b                   9.5919(9)
_cell_length_c                   23.752(2)
_cell_angle_alpha                90.2900(10)
_cell_angle_beta                 95.1460(10)
_cell_angle_gamma                105.614(2)
_cell_volume                     1626.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1343
_cell_measurement_theta_min      2.844
_cell_measurement_theta_max      25.632

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             813
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8318
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.1229
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5626
_reflns_number_gt                3222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)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         5626
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.0000 0.0000 0.0000 0.0280(3) Uani 1 2 d S . .
Co2 Co 0.16789(11) 0.26276(8) 0.53202(3) 0.0298(2) Uani 1 1 d . . .
N1 N 0.2204(7) 0.2049(5) 0.0157(2) 0.0418(13) Uani 1 1 d . . .
N2 N 0.5003(7) 0.6019(5) 0.1008(2) 0.0405(13) Uani 1 1 d . . .
H2 H 0.4527 0.6720 0.0919 0.049 Uiso 1 1 calc R . .
N3 N 0.8390(7) 1.5671(5) 0.41343(19) 0.0361(12) Uani 1 1 d . . .
N4 N 0.7921(7) 1.2081(5) 0.30525(19) 0.0366(12) Uani 1 1 d . . .
H4 H 0.7431 1.1268 0.3202 0.044 Uiso 1 1 calc R . .
O1 O 0.5526(6) -0.0270(4) 0.35765(16) 0.0423(11) Uani 1 1 d . . .
O2 O 0.3185(6) -0.2173(5) 0.37512(16) 0.0470(11) Uani 1 1 d . . .
O3 O 0.0721(6) -0.0571(4) 0.08217(15) 0.0358(10) Uani 1 1 d . . .
O4 O 0.2389(6) -0.2187(4) 0.07428(16) 0.0439(11) Uani 1 1 d . . .
O5 O 0.1409(6) 0.1678(4) 0.45003(16) 0.0420(11) Uani 1 1 d . . .
O6 O 0.2550(6) 0.4042(4) 0.45607(17) 0.0455(11) Uani 1 1 d . . .
O7 O 0.7357(8) 0.5468(5) 0.1564(2) 0.090(2) Uani 1 1 d . . .
O8 O 0.9190(7) 1.3079(5) 0.22600(18) 0.0601(13) Uani 1 1 d . . .
O9 O -0.1939(6) 0.1094(4) 0.03054(16) 0.0460(11) Uani 1 1 d . . .
H9C H -0.2081 0.1431 -0.0021 0.055 Uiso 1 1 d R . .
H9D H -0.1508 0.1801 0.0541 0.055 Uiso 1 1 d R . .
O10 O 0.1560(6) 0.0799(5) 0.57867(19) 0.0635(14) Uani 1 1 d . . .
H10C H 0.2452 0.0586 0.5985 0.076 Uiso 1 1 d R . .
H10D H 0.0691 0.0025 0.5709 0.076 Uiso 1 1 d R . .
O11 O 0.4676(5) 0.3117(4) 0.54511(16) 0.0466(11) Uani 1 1 d . . .
H11C H 0.5230 0.2708 0.5701 0.056 Uiso 1 1 d R . .
H11D H 0.5370 0.3966 0.5412 0.056 Uiso 1 1 d R . .
O12 O -0.1343(6) 0.1947(5) 0.52841(17) 0.0580(13) Uani 1 1 d . . .
H12C H -0.1868 0.2091 0.5574 0.070 Uiso 1 1 d R . .
H12D H -0.1589 0.1038 0.5222 0.070 Uiso 1 1 d R . .
O13 O 0.9555(7) 0.3527(5) 0.11079(19) 0.0775(16) Uani 1 1 d . . .
H13C H 0.8936 0.4151 0.1121 0.093 Uiso 1 1 d R . .
H13D H 0.9655 0.3197 0.1437 0.093 Uiso 1 1 d R . .
O14 O 0.505(3) 0.9700(14) 0.5207(5) 0.114(5) Uani 0.50 1 d P . .
H14C H 0.4870 0.9677 0.5556 0.136 Uiso 0.50 1 d PR . .
H14D H 0.5071 0.8862 0.5096 0.136 Uiso 0.50 1 d PR . .
C1 C 0.3987(9) -0.1201(6) 0.3432(2) 0.0326(14) Uani 1 1 d . . .
C2 C 0.1676(8) -0.1404(7) 0.1026(2) 0.0367(15) Uani 1 1 d . . .
C3 C 0.3099(8) -0.1202(6) 0.2831(2) 0.0294(13) Uani 1 1 d . . .
C4 C 0.2875(8) 0.0049(6) 0.2554(2) 0.0291(13) Uani 1 1 d . . .
C5 C 0.2307(8) -0.0080(6) 0.1972(2) 0.0320(14) Uani 1 1 d . . .
H5 H 0.2101 0.0722 0.1787 0.038 Uiso 1 1 calc R . .
C6 C 0.2043(8) -0.1364(6) 0.1664(2) 0.0284(13) Uani 1 1 d . . .
C7 C 0.2176(8) -0.2614(6) 0.1951(2) 0.0327(14) Uani 1 1 d . . .
H7 H 0.1936 -0.3496 0.1755 0.039 Uiso 1 1 calc R . .
C8 C 0.2666(8) -0.2523(6) 0.2527(2) 0.0360(15) Uani 1 1 d . . .
H8 H 0.2710 -0.3359 0.2718 0.043 Uiso 1 1 calc R . .
C9 C 0.2177(8) 0.2877(6) 0.4273(2) 0.0331(14) Uani 1 1 d . . .
C10 C 0.2702(8) 0.2848(6) 0.3676(2) 0.0308(14) Uani 1 1 d . . .
C11 C 0.2541(8) 0.1535(6) 0.3405(2) 0.0338(14) Uani 1 1 d . . .
H11 H 0.2041 0.0680 0.3587 0.041 Uiso 1 1 calc R . .
C12 C 0.3120(8) 0.1469(6) 0.2859(2) 0.0308(14) Uani 1 1 d . . .
C13 C 0.3868(8) 0.2767(6) 0.2600(2) 0.0386(15) Uani 1 1 d . . .
H13 H 0.4265 0.2748 0.2241 0.046 Uiso 1 1 calc R . .
C14 C 0.4032(9) 0.4086(6) 0.2867(3) 0.0424(16) Uani 1 1 d . . .
H14 H 0.4534 0.4940 0.2685 0.051 Uiso 1 1 calc R . .
C15 C 0.3443(8) 0.4147(6) 0.3413(2) 0.0382(15) Uani 1 1 d . . .
H15 H 0.3547 0.5032 0.3592 0.046 Uiso 1 1 calc R . .
C16 C 0.3658(9) 0.2138(6) 0.0548(3) 0.0472(18) Uani 1 1 d . . .
H16 H 0.4011 0.1296 0.0629 0.057 Uiso 1 1 calc R . .
C17 C 0.4663(9) 0.3402(7) 0.0837(3) 0.0457(17) Uani 1 1 d . . .
H17 H 0.5642 0.3400 0.1109 0.055 Uiso 1 1 calc R . .
C18 C 0.4180(9) 0.4669(6) 0.0715(2) 0.0373(15) Uani 1 1 d . . .
C19 C 0.2765(8) 0.4617(6) 0.0287(3) 0.0408(16) Uani 1 1 d . . .
H19 H 0.2456 0.5460 0.0178 0.049 Uiso 1 1 calc R . .
C20 C 0.1831(9) 0.3319(6) 0.0026(2) 0.0414(16) Uani 1 1 d . . .
H20 H 0.0883 0.3309 -0.0259 0.050 Uiso 1 1 calc R . .
C21 C 0.7746(9) 1.4297(7) 0.4288(2) 0.0418(16) Uani 1 1 d . . .
H21 H 0.7364 1.4134 0.4649 0.050 Uiso 1 1 calc R . .
C22 C 0.7615(8) 1.3107(6) 0.3941(2) 0.0386(15) Uani 1 1 d . . .
H22 H 0.7180 1.2174 0.4070 0.046 Uiso 1 1 calc R . .
C23 C 0.8145(8) 1.3328(6) 0.3395(2) 0.0300(14) Uani 1 1 d . . .
C24 C 0.8839(8) 1.4737(6) 0.3231(2) 0.0376(15) Uani 1 1 d . . .
H24 H 0.9240 1.4926 0.2872 0.045 Uiso 1 1 calc R . .
C25 C 0.8925(9) 1.5860(6) 0.3609(2) 0.0415(16) Uani 1 1 d . . .
H25 H 0.9382 1.6803 0.3492 0.050 Uiso 1 1 calc R . .
C26 C 0.6464(10) 0.6309(7) 0.1415(3) 0.0474(18) Uani 1 1 d . . .
C27 C 0.8385(9) 1.1999(6) 0.2509(3) 0.0362(15) Uani 1 1 d . . .
C28 C 0.6960(8) 0.7792(6) 0.1689(3) 0.0370(15) Uani 1 1 d . . .
C29 C 0.6778(9) 0.9018(6) 0.1404(3) 0.0402(16) Uani 1 1 d . . .
H29 H 0.6326 0.8926 0.1024 0.048 Uiso 1 1 calc R . .
C30 C 0.7247(8) 1.0355(6) 0.1669(2) 0.0377(15) Uani 1 1 d . . .
H30 H 0.7143 1.1160 0.1465 0.045 Uiso 1 1 calc R . .
C31 C 0.7882(8) 1.0522(6) 0.2244(2) 0.0344(14) Uani 1 1 d . . .
C32 C 0.8076(8) 0.9301(7) 0.2534(3) 0.0407(16) Uani 1 1 d . . .
H32 H 0.8506 0.9388 0.2916 0.049 Uiso 1 1 calc R . .
C33 C 0.7634(8) 0.7961(7) 0.2257(3) 0.0420(16) Uani 1 1 d . . .
H33 H 0.7791 0.7161 0.2455 0.050 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 O3 2.093(4) 2 ?
Co1 O3 2.093(4) . ?
Co1 O9 2.170(4) 2 ?
Co1 O9 2.170(4) . ?
Co1 N1 2.200(5) . ?
Co1 N1 2.200(5) 2 ?
Co2 O10 2.066(4) . ?
Co2 N3 2.093(4) 2_676 ?
Co2 O5 2.116(4) . ?
Co2 O11 2.146(4) . ?
Co2 O12 2.162(4) . ?
Co2 O6 2.297(4) . ?
N1 C16 1.345(7) . ?
N1 C20 1.353(7) . ?
N2 C26 1.357(7) . ?
N2 C18 1.423(7) . ?
N3 C21 1.341(7) . ?
N3 C25 1.343(7) . ?
N3 Co2 2.093(4) 2_676 ?
N4 C27 1.372(7) . ?
N4 C23 1.407(6) . ?
O1 C1 1.267(7) . ?
O2 C1 1.260(6) . ?
O3 C2 1.276(6) . ?
O4 C2 1.253(7) . ?
O5 C9 1.284(7) . ?
O6 C9 1.259(6) . ?
O7 C26 1.211(7) . ?
O8 C27 1.233(7) . ?
O14 O14 1.15(2) 2_676 ?
C1 C3 1.517(7) . ?
C2 C6 1.514(7) . ?
C3 C8 1.400(7) . ?
C3 C4 1.413(7) . ?
C4 C5 1.404(7) . ?
C4 C12 1.498(7) . ?
C5 C6 1.388(7) . ?
C6 C7 1.405(7) . ?
C7 C8 1.380(7) . ?
C9 C10 1.506(8) . ?
C10 C11 1.382(7) . ?
C10 C15 1.397(8) . ?
C11 C12 1.411(7) . ?
C12 C13 1.390(7) . ?
C13 C14 1.382(8) . ?
C14 C15 1.411(8) . ?
C16 C17 1.383(8) . ?
C17 C18 1.382(8) . ?
C18 C19 1.387(8) . ?
C19 C20 1.366(8) . ?
C21 C22 1.381(8) . ?
C22 C23 1.389(7) . ?
C23 C24 1.382(8) . ?
C24 C25 1.383(7) . ?
C26 C28 1.499(8) . ?
C27 C31 1.485(8) . ?
C28 C33 1.390(8) . ?
C28 C29 1.393(8) . ?
C29 C30 1.370(7) . ?
C30 C31 1.399(7) . ?
C31 C32 1.395(8) . ?
C32 C33 1.384(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Co1 O3 180.0(2) 2 . ?
O3 Co1 O9 91.13(14) 2 2 ?
O3 Co1 O9 88.87(14) . 2 ?
O3 Co1 O9 88.87(14) 2 . ?
O3 Co1 O9 91.13(14) . . ?
O9 Co1 O9 180.00(18) 2 . ?
O3 Co1 N1 92.10(17) 2 . ?
O3 Co1 N1 87.90(17) . . ?
O9 Co1 N1 92.35(17) 2 . ?
O9 Co1 N1 87.65(17) . . ?
O3 Co1 N1 87.90(17) 2 2 ?
O3 Co1 N1 92.10(17) . 2 ?
O9 Co1 N1 87.65(17) 2 2 ?
O9 Co1 N1 92.35(17) . 2 ?
N1 Co1 N1 180.0(3) . 2 ?
O10 Co2 N3 108.75(19) . 2_676 ?
O10 Co2 O5 98.77(17) . . ?
N3 Co2 O5 151.40(17) 2_676 . ?
O10 Co2 O11 87.82(16) . . ?
N3 Co2 O11 92.32(17) 2_676 . ?
O5 Co2 O11 96.43(15) . . ?
O10 Co2 O12 84.89(17) . . ?
N3 Co2 O12 87.66(18) 2_676 . ?
O5 Co2 O12 87.17(16) . . ?
O11 Co2 O12 172.30(15) . . ?
O10 Co2 O6 152.28(17) . . ?
N3 Co2 O6 95.97(17) 2_676 . ?
O5 Co2 O6 59.53(15) . . ?
O11 Co2 O6 78.63(15) . . ?
O12 Co2 O6 109.04(15) . . ?
C16 N1 C20 115.6(5) . . ?
C16 N1 Co1 120.4(4) . . ?
C20 N1 Co1 119.9(4) . . ?
C26 N2 C18 126.4(5) . . ?
C21 N3 C25 116.2(5) . . ?
C21 N3 Co2 119.9(4) . 2_676 ?
C25 N3 Co2 123.7(4) . 2_676 ?
C27 N4 C23 128.1(5) . . ?
C2 O3 Co1 133.8(4) . . ?
C9 O5 Co2 94.0(3) . . ?
C9 O6 Co2 86.4(4) . . ?
O2 C1 O1 123.8(6) . . ?
O2 C1 C3 117.7(5) . . ?
O1 C1 C3 118.4(5) . . ?
O4 C2 O3 125.5(5) . . ?
O4 C2 C6 118.4(5) . . ?
O3 C2 C6 116.0(5) . . ?
C8 C3 C4 119.4(5) . . ?
C8 C3 C1 115.9(5) . . ?
C4 C3 C1 124.3(5) . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 C12 119.2(5) . . ?
C3 C4 C12 123.0(5) . . ?
C6 C5 C4 122.3(5) . . ?
C5 C6 C7 119.0(5) . . ?
C5 C6 C2 120.4(5) . . ?
C7 C6 C2 120.6(5) . . ?
C8 C7 C6 119.5(5) . . ?
C7 C8 C3 121.6(5) . . ?
O6 C9 O5 119.5(5) . . ?
O6 C9 C10 121.4(6) . . ?
O5 C9 C10 119.1(5) . . ?
C11 C10 C15 120.5(5) . . ?
C11 C10 C9 119.7(5) . . ?
C15 C10 C9 119.7(5) . . ?
C10 C11 C12 121.2(6) . . ?
C13 C12 C11 118.0(5) . . ?
C13 C12 C4 120.7(5) . . ?
C11 C12 C4 121.3(5) . . ?
C14 C13 C12 121.3(6) . . ?
C13 C14 C15 120.5(6) . . ?
C10 C15 C14 118.5(5) . . ?
N1 C16 C17 124.2(5) . . ?
C16 C17 C18 118.6(6) . . ?
C17 C18 C19 118.0(6) . . ?
C17 C18 N2 124.4(6) . . ?
C19 C18 N2 117.6(5) . . ?
C20 C19 C18 119.5(6) . . ?
N1 C20 C19 123.8(6) . . ?
N3 C21 C22 123.9(5) . . ?
C21 C22 C23 118.9(6) . . ?
C24 C23 C22 118.2(5) . . ?
C24 C23 N4 125.3(5) . . ?
C22 C23 N4 116.6(5) . . ?
C23 C24 C25 118.8(5) . . ?
N3 C25 C24 124.0(6) . . ?
O7 C26 N2 124.9(6) . . ?
O7 C26 C28 119.5(6) . . ?
N2 C26 C28 115.6(5) . . ?
O8 C27 N4 122.1(5) . . ?
O8 C27 C31 122.1(6) . . ?
N4 C27 C31 115.7(5) . . ?
C33 C28 C29 117.9(5) . . ?
C33 C28 C26 118.8(5) . . ?
C29 C28 C26 123.3(6) . . ?
C30 C29 C28 121.6(6) . . ?
C29 C30 C31 120.6(5) . . ?
C32 C31 C30 118.3(5) . . ?
C32 C31 C27 123.4(6) . . ?
C30 C31 C27 118.3(5) . . ?
C31 C32 C33 120.5(6) . . ?
C28 C33 C32 121.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.977
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.108
