# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3
_database_code_depnum_ccdc_archive 'CCDC 1494895'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H28 N4 O10 Zn2'
_chemical_formula_sum            'C27 H28 N4 O10 Zn2'
_chemical_formula_weight         699.27

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.8940(4)
_cell_length_b                   13.8940(4)
_cell_length_c                   28.8987(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5578.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    34778
_cell_measurement_theta_min      1.41
_cell_measurement_theta_max      26.69

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             2864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    1.786
_shelx_estimated_absorpt_T_min   0.469
_shelx_estimated_absorpt_T_max   0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7884
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(MULABS; Spek, 2009)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38089
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2784
_reflns_number_gt                2653
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014/6 (Sheldrick, 2015) and PLATON (Spek, 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1226 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     202
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0496
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.60341(2) 0.69479(2) 0.70603(2) 0.02013(10) Uani 1 1 d . . . . .
O1 O 0.6283(2) 0.60528(17) 0.65591(9) 0.0350(6) Uani 1 1 d . . . . .
O2 O 0.62074(16) 0.48417(16) 0.70549(11) 0.0332(5) Uani 1 1 d . . . . .
O3 O 0.68945(17) 0.17562(16) 0.51401(9) 0.0261(5) Uani 1 1 d . . . . .
O4 O 0.70036(17) 0.30578(17) 0.46888(8) 0.0291(6) Uani 1 1 d . . . . .
O1W O 0.46638(16) 0.67723(17) 0.72619(9) 0.0266(5) Uani 1 1 d D . . . .
H1WA H 0.437(3) 0.626(2) 0.7203(15) 0.040 Uiso 1 1 d D U . . .
H1WB H 0.426(3) 0.718(3) 0.7208(15) 0.040 Uiso 1 1 d D U . . .
N1 N 0.6021(2) 0.8271(2) 0.67817(11) 0.0296(6) Uani 1 1 d . . . . .
N2 N 0.59828(19) 0.9479(2) 0.62959(11) 0.0289(6) Uani 1 1 d . . . . .
C1 C 0.6292(2) 0.5160(2) 0.66559(11) 0.0242(7) Uani 1 1 d . . . . .
C2 C 0.6427(2) 0.4497(2) 0.62482(11) 0.0219(6) Uani 1 1 d . . . . .
C3 C 0.6747(2) 0.3554(2) 0.63133(11) 0.0219(6) Uani 1 1 d . . . . .
H3 H 0.6873 0.3327 0.6614 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6880(2) 0.2949(2) 0.59344(11) 0.0221(6) Uani 1 1 d . . . . .
H4 H 0.7092 0.2313 0.5980 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6700(2) 0.3283(2) 0.54922(11) 0.0200(6) Uani 1 1 d . . . . .
C6 C 0.6879(2) 0.2671(2) 0.50719(11) 0.0221(6) Uani 1 1 d . . . . .
C7 C 0.6373(3) 0.4227(2) 0.54278(12) 0.0267(7) Uani 1 1 d . . . . .
H7 H 0.6242 0.4453 0.5128 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6242(2) 0.4827(2) 0.58038(12) 0.0275(7) Uani 1 1 d . . . . .
H8 H 0.6028 0.5462 0.5758 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5878(2) 0.8532(3) 0.63470(13) 0.0288(7) Uani 1 1 d . . . . .
C10 C 0.6226(2) 0.9847(3) 0.67269(14) 0.0318(7) Uani 1 1 d . . . . .
H10 H 0.6350 1.0495 0.6799 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6250(2) 0.9113(2) 0.70142(16) 0.0318(8) Uani 1 1 d . . . . .
H11 H 0.6400 0.9153 0.7331 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5933(2) 1.0062(3) 0.58696(12) 0.0303(8) Uani 1 1 d . . . . .
H12A H 0.6463 0.9867 0.5667 0.036 Uiso 1 1 calc R U . . .
H12B H 0.6040 1.0737 0.5953 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5000 1.0000 0.55952(15) 0.0338(11) Uani 1 2 d S T P . .
H13A H 0.4962 1.0567 0.5394 0.041 Uiso 1 1 d R U . . .
C14 C 0.5644(3) 0.7857(3) 0.59584(15) 0.0399(9) Uani 1 1 d . . . . .
H14A H 0.5808 0.7204 0.6048 0.060 Uiso 1 1 calc R U . . .
H14B H 0.6011 0.8036 0.5686 0.060 Uiso 1 1 calc R U . . .
H14C H 0.4962 0.7893 0.5889 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.940(2) . ?
Zn1 O3 1.954(2) 8 ?
Zn1 O1W 2.006(2) . ?
Zn1 N1 2.008(3) . ?
O1 C1 1.272(4) . ?
O2 C1 1.241(4) . ?
O3 C6 1.286(4) . ?
O3 Zn1 1.954(2) 16_444 ?
O4 C6 1.243(4) . ?
O1W H1WA 0.83(3) . ?
O1W H1WB 0.81(3) . ?
N1 C9 1.323(5) . ?
N1 C11 1.385(5) . ?
N2 C9 1.331(5) . ?
N2 C10 1.389(5) . ?
N2 C12 1.476(4) . ?
C1 C2 1.508(4) . ?
C2 C8 1.388(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.393(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9400 . ?
C5 C7 1.401(5) . ?
C5 C6 1.503(4) . ?
C7 C8 1.382(5) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C14 1.499(5) . ?
C10 C11 1.316(6) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.522(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C12 1.522(4) 11_564 ?
C13 H13A 0.9802 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

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 Zn1 O3 121.61(10) . 8 ?
O1 Zn1 O1W 107.95(11) . . ?
O3 Zn1 O1W 103.51(10) 8 . ?
O1 Zn1 N1 106.82(12) . . ?
O3 Zn1 N1 112.53(12) 8 . ?
O1W Zn1 N1 102.67(11) . . ?
C1 O1 Zn1 117.6(2) . . ?
C6 O3 Zn1 112.1(2) . 16_444 ?
Zn1 O1W H1WA 120(3) . . ?
Zn1 O1W H1WB 121(3) . . ?
H1WA O1W H1WB 102(4) . . ?
C9 N1 C11 105.3(3) . . ?
C9 N1 Zn1 129.3(3) . . ?
C11 N1 Zn1 125.2(3) . . ?
C9 N2 C10 106.9(3) . . ?
C9 N2 C12 129.0(3) . . ?
C10 N2 C12 123.9(3) . . ?
O2 C1 O1 123.4(3) . . ?
O2 C1 C2 121.4(3) . . ?
O1 C1 C2 115.2(3) . . ?
C8 C2 C3 119.6(3) . . ?
C8 C2 C1 119.9(3) . . ?
C3 C2 C1 120.5(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C7 119.7(3) . . ?
C4 C5 C6 121.8(3) . . ?
C7 C5 C6 118.4(3) . . ?
O4 C6 O3 124.2(3) . . ?
O4 C6 C5 119.9(3) . . ?
O3 C6 C5 116.0(3) . . ?
C8 C7 C5 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C5 C7 H7 119.9 . . ?
C7 C8 C2 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C2 C8 H8 119.9 . . ?
N1 C9 N2 111.1(3) . . ?
N1 C9 C14 124.9(3) . . ?
N2 C9 C14 124.0(3) . . ?
C11 C10 N2 106.6(3) . . ?
C11 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
C10 C11 N1 110.0(4) . . ?
C10 C11 H11 125.0 . . ?
N1 C11 H11 125.0 . . ?
N2 C12 C13 116.3(3) . . ?
N2 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
N2 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C12 117.2(4) . 11_564 ?
C12 C13 H13A 108.0 . . ?
C12 C13 H13A 108.0 11_564 . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Zn1 O1 C1 O2 -4.5(4) . . . . ?
Zn1 O1 C1 C2 176.3(2) . . . . ?
O2 C1 C2 C8 161.3(3) . . . . ?
O1 C1 C2 C8 -19.5(4) . . . . ?
O2 C1 C2 C3 -19.4(5) . . . . ?
O1 C1 C2 C3 159.8(3) . . . . ?
C8 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C7 -0.8(5) . . . . ?
C3 C4 C5 C6 177.0(3) . . . . ?
Zn1 O3 C6 O4 -8.4(4) 16_444 . . . ?
Zn1 O3 C6 C5 171.9(2) 16_444 . . . ?
C4 C5 C6 O4 -157.6(3) . . . . ?
C7 C5 C6 O4 20.3(4) . . . . ?
C4 C5 C6 O3 22.2(4) . . . . ?
C7 C5 C6 O3 -159.9(3) . . . . ?
C4 C5 C7 C8 0.9(5) . . . . ?
C6 C5 C7 C8 -177.0(3) . . . . ?
C5 C7 C8 C2 -0.5(5) . . . . ?
C3 C2 C8 C7 0.1(5) . . . . ?
C1 C2 C8 C7 179.4(3) . . . . ?
C11 N1 C9 N2 -1.2(4) . . . . ?
Zn1 N1 C9 N2 -176.3(2) . . . . ?
C11 N1 C9 C14 177.8(3) . . . . ?
Zn1 N1 C9 C14 2.8(5) . . . . ?
C10 N2 C9 N1 1.1(4) . . . . ?
C12 N2 C9 N1 176.8(3) . . . . ?
C10 N2 C9 C14 -178.0(3) . . . . ?
C12 N2 C9 C14 -2.3(5) . . . . ?
C9 N2 C10 C11 -0.4(4) . . . . ?
C12 N2 C10 C11 -176.4(3) . . . . ?
N2 C10 C11 N1 -0.4(4) . . . . ?
C9 N1 C11 C10 1.0(4) . . . . ?
Zn1 N1 C11 C10 176.3(2) . . . . ?
C9 N2 C12 C13 57.8(4) . . . . ?
C10 N2 C12 C13 -127.1(3) . . . . ?
N2 C12 C13 C12 37.9(2) . . . 11_564 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O2 0.83(3) 1.78(3) 2.618(3) 177(5) 11_554
O1W H1WB O4 0.81(3) 2.02(3) 2.814(3) 166(4) 14_464
C10 H10 O4 0.94 2.52 3.427(4) 163 7_655
C13 H13A O2 0.98 2.59 3.450(5) 147 16_454
C14 H14A O1 0.97 2.27 3.176(5) 154 .

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1494894'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu N4 O4, 6(H2 O)'
_chemical_formula_sum            'C19 H32 Cu N4 O10'
_chemical_formula_weight         540.02

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.1991(10)
_cell_length_b                   13.4825(8)
_cell_length_c                   14.6649(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.027(5)
_cell_angle_gamma                90
_cell_volume                     2500.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    17464
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      26.72

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1132
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.931
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(MULABS; Spek, 2009)'
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'φ + ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34541
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.656
_diffrn_reflns_theta_max         26.257
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5044
_reflns_number_gt                3674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014/6 (Sheldrick, 2015) and PLATON (Spek, 2009) 
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5044
_refine_ls_number_parameters     345
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.884
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.34303(2) 0.26036(2) 0.16801(2) 0.01701(7) Uani 1 1 d . . . . .
O1 O 0.19767(12) 0.30767(11) 0.12911(12) 0.0258(4) Uani 1 1 d . . . . .
O2 O 0.24014(13) 0.37864(11) 0.01650(12) 0.0275(4) Uani 1 1 d . . . . .
O3 O 0.40063(12) 0.38699(10) 0.24642(11) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.39639(12) 0.27123(11) 0.35136(11) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.30065(15) 0.12072(12) 0.13510(14) 0.0208(4) Uani 1 1 d . . . . .
N2 N 0.26310(15) -0.02442(12) 0.06008(14) 0.0219(4) Uani 1 1 d . . . . .
N3 N 0.48641(14) 0.22932(13) 0.18466(13) 0.0225(4) Uani 1 1 d . . . . .
N4 N 0.62984(15) 0.20984(13) 0.16636(15) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.18087(18) 0.37015(15) 0.05845(17) 0.0217(5) Uani 1 1 d . . . . .
C2 C 0.08590(17) 0.43618(15) 0.02697(17) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.07299(18) 0.51800(16) -0.03620(17) 0.0251(5) Uani 1 1 d . . . . .
H3 H 0.1223 0.5301 -0.0611 0.030 Uiso 1 1 calc R U . . .
C4 C 0.01221(18) 0.41872(16) 0.06222(18) 0.0242(5) Uani 1 1 d . . . . .
H4 H 0.0200 0.3635 0.1042 0.029 Uiso 1 1 calc R U . . .
C5 C 0.41602(17) 0.35795(15) 0.33513(17) 0.0194(5) Uani 1 1 d . . . . .
C6 C 0.46000(16) 0.43178(15) 0.42056(16) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.51209(17) 0.39908(15) 0.52144(17) 0.0199(5) Uani 1 1 d . . . . .
H7 H 0.5202 0.3308 0.5357 0.024 Uiso 1 1 calc R U . . .
C8 C 0.44804(17) 0.53316(15) 0.39923(17) 0.0199(5) Uani 1 1 d . . . . .
H8 H 0.4130 0.5553 0.3311 0.024 Uiso 1 1 calc R U . . .
C9 C 0.26245(17) 0.07485(15) 0.04601(17) 0.0210(5) Uani 1 1 d . . . . .
C10 C 0.30474(19) -0.04172(16) 0.16381(18) 0.0264(5) Uani 1 1 d . . . . .
H10 H 0.3152 -0.1037 0.1963 0.032 Uiso 1 1 calc R U . . .
C11 C 0.32759(18) 0.04804(15) 0.20950(18) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.3570 0.0594 0.2804 0.031 Uiso 1 1 calc R U . . .
C12 C 0.23357(19) -0.10056(16) -0.01944(19) 0.0271(5) Uani 1 1 d . . . . .
H12A H 0.1691 -0.0800 -0.0797 0.033 Uiso 1 1 calc R U . . .
H12B H 0.2186 -0.1629 0.0058 0.033 Uiso 1 1 calc R U . . .
C13 C 0.32133(19) -0.11704(17) -0.0496(2) 0.0314(6) Uani 1 1 d . . . . .
H13A H 0.3882 -0.1277 0.0122 0.038 Uiso 1 1 calc R U . . .
H13B H 0.3291 -0.0577 -0.0842 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2249(2) 0.12411(17) -0.05509(18) 0.0307(6) Uani 1 1 d . . . . .
H14A H 0.2765 0.1144 -0.0806 0.046 Uiso 1 1 calc R U . . .
H14B H 0.2160 0.1945 -0.0478 0.046 Uiso 1 1 calc R U . . .
H14C H 0.1578 0.0956 -0.1029 0.046 Uiso 1 1 calc R U . . .
C15 C 0.52950(16) 0.24473(16) 0.12272(15) 0.0229(4) Uani 1 1 d . . . . .
C16 C 0.65007(19) 0.16989(17) 0.25965(19) 0.0306(6) Uani 1 1 d . . . . .
H16 H 0.7132 0.1396 0.3067 0.037 Uiso 1 1 calc R U . . .
C17 C 0.56165(19) 0.18271(17) 0.27035(18) 0.0285(5) Uani 1 1 d . . . . .
H17 H 0.5527 0.1630 0.3274 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2981(2) -0.20611(17) -0.1201(2) 0.0318(6) Uani 1 1 d . . . . .
H18A H 0.3053 -0.2671 -0.0811 0.038 Uiso 1 1 calc R U . . .
H18B H 0.2250 -0.2022 -0.1743 0.038 Uiso 1 1 calc R U . . .
C19 C 0.4766(2) 0.2934(2) 0.02081(19) 0.0363(6) Uani 1 1 d . . . . .
H19A H 0.4072 0.3165 0.0087 0.054 Uiso 1 1 calc R U . . .
H19B H 0.4693 0.2461 -0.0319 0.054 Uiso 1 1 calc R U . . .
H19C H 0.5188 0.3493 0.0191 0.054 Uiso 1 1 calc R U . . .
O1W O 0.16071(19) 0.05207(15) 0.47728(17) 0.0393(5) Uani 1 1 d . . . . .
H1WA H 0.099(3) 0.043(2) 0.428(3) 0.062(11) Uiso 1 1 d . . . . .
H1WB H 0.189(3) 0.001(3) 0.477(3) 0.064(12) Uiso 1 1 d . . . . .
O2W O 0.19551(17) 0.04376(15) 0.68194(17) 0.0471(5) Uani 1 1 d D . . . .
H2WA H 0.188(3) 0.046(2) 0.6222(15) 0.071 Uiso 1 1 d D U . . .
H2WB H 0.2188(15) 0.086(2) 0.716(2) 0.071 Uiso 1 1 d D U . . .
O3W O 0.52767(18) 0.52574(14) 0.20687(16) 0.0390(5) Uani 1 1 d . . . . .
H3WA H 0.499(3) 0.483(2) 0.225(2) 0.053(10) Uiso 1 1 d . . . . .
H3WB H 0.574(3) 0.501(2) 0.199(3) 0.056(11) Uiso 1 1 d . . . . .
O4W O 0.2125(2) 0.19825(18) 0.3596(2) 0.0652(7) Uani 1 1 d . . . . .
H4WA H 0.223(3) 0.160(3) 0.407(3) 0.061(11) Uiso 1 1 d . . . . .
H4WB H 0.270(3) 0.214(3) 0.357(3) 0.083(13) Uiso 1 1 d . . . . .
O5W O -0.00378(19) 0.23178(16) 0.2591(2) 0.0705(7) Uani 1 1 d D . . . .
H5WA H 0.0608(15) 0.231(3) 0.282(3) 0.106 Uiso 1 1 d D U . . .
H5WB H -0.025(3) 0.1758(18) 0.262(3) 0.106 Uiso 1 1 d D U . . .
O6W O 0.41284(18) 0.09324(17) 0.79365(19) 0.0705(7) Uani 1 1 d D . . . .
H6WA H 0.4466 0.1449 0.7919 0.106 Uiso 1 1 d DR U . . .
H6WB H 0.3816 0.0823 0.7332 0.106 Uiso 1 1 d DR U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9687(17) . ?
Cu1 O1 1.9804(15) . ?
Cu1 N3 1.9818(18) . ?
Cu1 O3 2.0129(14) . ?
O1 C1 1.271(3) . ?
O2 C1 1.253(3) . ?
O3 C5 1.279(3) . ?
O4 C5 1.250(2) . ?
N1 C9 1.319(3) . ?
N1 C11 1.385(3) . ?
N2 C9 1.354(3) . ?
N2 C10 1.379(3) . ?
N2 C12 1.465(3) . ?
N3 C15 1.322(3) . ?
N3 C17 1.377(3) . ?
N4 C15 1.354(3) . ?
N4 C16 1.374(3) . ?
N4 C18 1.463(3) 3_655 ?
C1 C2 1.503(3) . ?
C2 C4 1.382(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.385(3) 3_565 ?
C3 H3 0.9400 . ?
C4 C3 1.385(3) 3_565 ?
C4 H4 0.9400 . ?
C5 C6 1.496(3) . ?
C6 C7 1.391(3) . ?
C6 C8 1.395(3) . ?
C7 C8 1.382(3) 3_666 ?
C7 H7 0.9400 . ?
C8 C7 1.382(3) 3_666 ?
C8 H8 0.9400 . ?
C9 C14 1.485(3) . ?
C10 C11 1.349(3) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C18 1.521(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C19 1.486(3) . ?
C16 C17 1.345(3) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 N4 1.463(3) 3_655 ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
O1W H1WA 0.85(4) . ?
O1W H1WB 0.80(4) . ?
O2W H2WA 0.836(17) . ?
O2W H2WB 0.734(17) . ?
O3W H3WA 0.81(3) . ?
O3W H3WB 0.79(3) . ?
O4W H4WA 0.82(3) . ?
O4W H4WB 0.86(4) . ?
O5W H5WA 0.821(18) . ?
O5W H5WB 0.819(18) . ?
O6W H6WA 0.8531 . ?
O6W H6WB 0.8039 . ?

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 O1 94.30(7) . . ?
N1 Cu1 N3 90.62(7) . . ?
O1 Cu1 N3 168.89(7) . . ?
N1 Cu1 O3 161.95(7) . . ?
O1 Cu1 O3 89.49(6) . . ?
N3 Cu1 O3 88.90(7) . . ?
C1 O1 Cu1 103.49(14) . . ?
C5 O3 Cu1 99.13(12) . . ?
C9 N1 C11 106.90(18) . . ?
C9 N1 Cu1 129.31(15) . . ?
C11 N1 Cu1 122.64(15) . . ?
C9 N2 C10 107.77(17) . . ?
C9 N2 C12 126.29(19) . . ?
C10 N2 C12 125.74(18) . . ?
C15 N3 C17 106.82(18) . . ?
C15 N3 Cu1 130.73(15) . . ?
C17 N3 Cu1 122.45(15) . . ?
C15 N4 C16 107.82(19) . . ?
C15 N4 C18 126.9(2) . 3_655 ?
C16 N4 C18 125.0(2) . 3_655 ?
O2 C1 O1 122.8(2) . . ?
O2 C1 C2 120.3(2) . . ?
O1 C1 C2 116.9(2) . . ?
C4 C2 C3 119.3(2) . . ?
C4 C2 C1 120.7(2) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 120.3(2) 3_565 . ?
C4 C3 H3 119.9 3_565 . ?
C2 C3 H3 119.9 . . ?
C2 C4 C3 120.5(2) . 3_565 ?
C2 C4 H4 119.8 . . ?
C3 C4 H4 119.8 3_565 . ?
O4 C5 O3 122.03(19) . . ?
O4 C5 C6 120.49(19) . . ?
O3 C5 C6 117.48(18) . . ?
C7 C6 C8 120.04(19) . . ?
C7 C6 C5 119.83(19) . . ?
C8 C6 C5 120.13(19) . . ?
C8 C7 C6 120.14(19) 3_666 . ?
C8 C7 H7 119.9 3_666 . ?
C6 C7 H7 119.9 . . ?
C7 C8 C6 119.8(2) 3_666 . ?
C7 C8 H8 120.1 3_666 . ?
C6 C8 H8 120.1 . . ?
N1 C9 N2 109.96(19) . . ?
N1 C9 C14 125.37(19) . . ?
N2 C9 C14 124.68(19) . . ?
C11 C10 N2 106.38(19) . . ?
C11 C10 H10 126.8 . . ?
N2 C10 H10 126.8 . . ?
C10 C11 N1 109.0(2) . . ?
C10 C11 H11 125.5 . . ?
N1 C11 H11 125.5 . . ?
N2 C12 C13 111.04(18) . . ?
N2 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C18 111.17(19) . . ?
C12 C13 H13A 109.4 . . ?
C18 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C18 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 N4 109.69(19) . . ?
N3 C15 C19 125.5(2) . . ?
N4 C15 C19 124.9(2) . . ?
C17 C16 N4 106.4(2) . . ?
C17 C16 H16 126.8 . . ?
N4 C16 H16 126.8 . . ?
C16 C17 N3 109.3(2) . . ?
C16 C17 H17 125.4 . . ?
N3 C17 H17 125.4 . . ?
N4 C18 C13 111.18(19) 3_655 . ?
N4 C18 H18A 109.4 3_655 . ?
C13 C18 H18A 109.4 . . ?
N4 C18 H18B 109.4 3_655 . ?
C13 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1WA O1W H1WB 101(3) . . ?
H2WA O2W H2WB 120(3) . . ?
H3WA O3W H3WB 109(3) . . ?
H4WA O4W H4WB 112(4) . . ?
H5WA O5W H5WB 109(3) . . ?
H6WA O6W H6WB 98.8 . . ?

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 O1 C1 O2 11.9(2) . . . . ?
Cu1 O1 C1 C2 -167.34(15) . . . . ?
O2 C1 C2 C4 171.1(2) . . . . ?
O1 C1 C2 C4 -9.7(3) . . . . ?
O2 C1 C2 C3 -10.8(3) . . . . ?
O1 C1 C2 C3 168.37(19) . . . . ?
C4 C2 C3 C4 0.6(4) . . . 3_565 ?
C1 C2 C3 C4 -177.5(2) . . . 3_565 ?
C3 C2 C4 C3 -0.6(4) . . . 3_565 ?
C1 C2 C4 C3 177.5(2) . . . 3_565 ?
Cu1 O3 C5 O4 0.8(2) . . . . ?
Cu1 O3 C5 C6 -179.86(15) . . . . ?
O4 C5 C6 C7 21.7(3) . . . . ?
O3 C5 C6 C7 -157.7(2) . . . . ?
O4 C5 C6 C8 -157.7(2) . . . . ?
O3 C5 C6 C8 22.9(3) . . . . ?
C8 C6 C7 C8 0.1(4) . . . 3_666 ?
C5 C6 C7 C8 -179.34(19) . . . 3_666 ?
C7 C6 C8 C7 -0.1(3) . . . 3_666 ?
C5 C6 C8 C7 179.34(19) . . . 3_666 ?
C11 N1 C9 N2 0.4(2) . . . . ?
Cu1 N1 C9 N2 168.18(15) . . . . ?
C11 N1 C9 C14 -179.1(2) . . . . ?
Cu1 N1 C9 C14 -11.4(3) . . . . ?
C10 N2 C9 N1 -0.5(2) . . . . ?
C12 N2 C9 N1 -175.6(2) . . . . ?
C10 N2 C9 C14 179.1(2) . . . . ?
C12 N2 C9 C14 3.9(4) . . . . ?
C9 N2 C10 C11 0.3(3) . . . . ?
C12 N2 C10 C11 175.5(2) . . . . ?
N2 C10 C11 N1 -0.1(3) . . . . ?
C9 N1 C11 C10 -0.2(3) . . . . ?
Cu1 N1 C11 C10 -168.97(16) . . . . ?
C9 N2 C12 C13 77.5(3) . . . . ?
C10 N2 C12 C13 -96.8(3) . . . . ?
N2 C12 C13 C18 171.6(2) . . . . ?
C17 N3 C15 N4 -0.3(2) . . . . ?
Cu1 N3 C15 N4 -179.27(14) . . . . ?
C17 N3 C15 C19 -179.9(2) . . . . ?
Cu1 N3 C15 C19 1.0(3) . . . . ?
C16 N4 C15 N3 0.6(2) . . . . ?
C18 N4 C15 N3 175.35(19) 3_655 . . . ?
C16 N4 C15 C19 -179.7(2) . . . . ?
C18 N4 C15 C19 -5.0(3) 3_655 . . . ?
C15 N4 C16 C17 -0.6(3) . . . . ?
C18 N4 C16 C17 -175.6(2) 3_655 . . . ?
N4 C16 C17 N3 0.5(3) . . . . ?
C15 N3 C17 C16 -0.2(3) . . . . ?
Cu1 N3 C17 C16 178.95(15) . . . . ?
C12 C13 C18 N4 168.0(2) . . . 3_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O3W 0.85(4) 2.00(4) 2.830(3) 167(3) 2_545
O1W H1WB O2 0.80(4) 1.91(4) 2.709(3) 178(4) 2_545
O2W H2WA O1W 0.836(17) 1.979(17) 2.814(3) 176(4) .
O2W H2WB O6W 0.734(17) 2.459(19) 2.838(3) 114.1(19) .
O3W H3WA O3 0.81(3) 2.03(3) 2.836(3) 169(3) .
O3W H3WB O2W 0.79(3) 1.95(4) 2.736(3) 173(3) 4_665
O4W H4WA O1W 0.82(3) 2.20(4) 2.925(3) 149(3) .
O4W H4WB O4 0.86(4) 1.99(4) 2.845(3) 171(4) .
O5W H5WA O4W 0.821(18) 1.97(2) 2.773(3) 164(4) .
O5W H5WB O3W 0.819(18) 2.08(2) 2.870(3) 162(4) 2_545
O6W H6WA O5W 0.85 1.95 2.787(3) 167 4_666
O6W H6WB O2W 0.80 2.45 2.838(3) 111 .
C12 H12B O4W 0.98 2.57 3.436(4) 148 2_545
C14 H14B O2 0.97 2.62 3.566(3) 165 .
C19 H19A O2 0.97 2.57 3.522(3) 168 .


_refine_diff_density_max         0.325
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1494893'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 Co2 N4 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C33 H38 Co2 N6 O10'
_chemical_formula_weight         796.55

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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.3638(12)
_cell_length_b                   10.9135(4)
_cell_length_c                   18.8942(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.374(5)
_cell_angle_gamma                90
_cell_volume                     3593.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    19903
_cell_measurement_theta_min      1.35
_cell_measurement_theta_max      26.65

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.987
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8962
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(MULABS; Spek, 2009)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37738
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.348
_diffrn_reflns_theta_max         26.229
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7228
_reflns_number_gt                4696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014/6 (Sheldrick, 2015) and PLATON (Spek, 2009)
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   cifmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7228
_refine_ls_number_parameters     466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.18635(2) 0.29472(4) 0.47069(2) 0.01684(10) Uani 1 1 d . . . . .
Co2 Co 0.28547(2) 0.29775(4) 0.37667(2) 0.01610(10) Uani 1 1 d . . . . .
O1 O 0.11172(13) 0.3015(2) 0.36397(11) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.18544(12) 0.3057(2) 0.28995(11) 0.0299(5) Uani 1 1 d . . . . .
O3 O 0.25962(14) 0.1177(2) 0.38731(13) 0.0338(6) Uani 1 1 d . . . . .
O4 O 0.18782(16) 0.1106(2) 0.46227(14) 0.0400(6) Uani 1 1 d . . . . .
O5 O 0.28131(13) 0.4815(2) 0.39262(12) 0.0271(5) Uani 1 1 d . . . . .
O6 O 0.20443(14) 0.4791(2) 0.46415(13) 0.0301(6) Uani 1 1 d . . . . .
O7 O -0.21096(13) 0.2149(3) 0.05285(12) 0.0367(6) Uani 1 1 d . . . . .
O8 O -0.13533(13) 0.2179(2) -0.01935(11) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.10528(15) 0.3257(2) 0.52198(14) 0.0235(6) Uani 1 1 d . . . . .
N2 N 0.04164(16) 0.4047(3) 0.59159(14) 0.0280(6) Uani 1 1 d . . . . .
N3 N -0.07349(16) 0.2262(3) 0.73942(15) 0.0293(7) Uani 1 1 d . . . . .
N4 N -0.13943(14) 0.1873(2) 0.81585(13) 0.0216(6) Uani 1 1 d . . . . .
C1 C 0.12169(18) 0.2968(3) 0.30130(16) 0.0225(6) Uani 1 1 d . . . . .
C2 C 0.22508(19) 0.0614(3) 0.42456(18) 0.0252(7) Uani 1 1 d . . . . .
C3 C 0.23038(19) -0.0750(3) 0.42573(18) 0.0226(7) Uani 1 1 d . . . . .
C4 C 0.2092(2) -0.1415(3) 0.47964(18) 0.0250(7) Uani 1 1 d . . . . .
H4A H 0.1905 -0.1004 0.5141 0.030 Uiso 1 1 calc R U . . .
C5 C 0.25712(19) -0.1369(3) 0.37473(18) 0.0244(7) Uani 1 1 d . . . . .
H5A H 0.2714 -0.0925 0.3386 0.029 Uiso 1 1 calc R U . . .
C6 C 0.24353(19) 0.5328(3) 0.42987(17) 0.0211(6) Uani 1 1 d . . . . .
C7 C 0.24215(19) 0.6699(3) 0.43074(17) 0.0212(6) Uani 1 1 d . . . . .
C8 C 0.21584(19) -0.2679(3) 0.48200(17) 0.0247(7) Uani 1 1 d . . . . .
H8A H 0.2024 -0.3121 0.5187 0.030 Uiso 1 1 calc R U . . .
C9 C 0.26292(19) -0.2639(3) 0.37662(18) 0.0254(8) Uani 1 1 d . . . . .
H9A H 0.2807 -0.3052 0.3416 0.031 Uiso 1 1 calc R U . . .
C10 C 0.05139(17) 0.2793(3) 0.23478(16) 0.0206(6) Uani 1 1 d . . . . .
C11 C 0.05623(17) 0.2914(3) 0.16288(16) 0.0256(7) Uani 1 1 d . . . . .
H11 H 0.1036 0.3107 0.1563 0.031 Uiso 1 1 calc R U . . .
C12 C -0.00828(18) 0.2753(3) 0.10106(17) 0.0269(8) Uani 1 1 d . . . . .
H12 H -0.0044 0.2839 0.0529 0.032 Uiso 1 1 calc R U . . .
C13 C -0.07873(18) 0.2464(3) 0.11001(17) 0.0221(7) Uani 1 1 d . . . . .
C14 C -0.14666(18) 0.2250(3) 0.04217(17) 0.0247(7) Uani 1 1 d . . . . .
C15 C -0.08367(18) 0.2356(3) 0.18126(17) 0.0271(7) Uani 1 1 d . . . . .
H15 H -0.1311 0.2166 0.1878 0.032 Uiso 1 1 calc R U . . .
C16 C -0.01933(19) 0.2525(3) 0.24322(17) 0.0250(7) Uani 1 1 d . . . . .
H16 H -0.0237 0.2458 0.2913 0.030 Uiso 1 1 calc R U . . .
C17 C 0.11166(18) 0.3878(3) 0.58426(16) 0.0242(7) Uani 1 1 d . . . . .
C18 C -0.0115(2) 0.3521(4) 0.53113(19) 0.0368(9) Uani 1 1 d . . . . .
H18 H -0.0649 0.3504 0.5211 0.044 Uiso 1 1 calc R U . . .
C19 C 0.02817(18) 0.3038(3) 0.48918(17) 0.0305(7) Uani 1 1 d . . . . .
H19 H 0.0065 0.2614 0.4441 0.037 Uiso 1 1 calc R U . . .
C20 C 0.0244(2) 0.4678(3) 0.65302(19) 0.0346(8) Uani 1 1 d . . . . .
H20A H -0.0238 0.5130 0.6331 0.042 Uiso 1 1 calc R U . . .
H20B H 0.0651 0.5275 0.6753 0.042 Uiso 1 1 calc R U . . .
C21 C 0.0177(2) 0.3800(3) 0.71364(19) 0.0350(8) Uani 1 1 d . . . . .
H21A H 0.0658 0.3343 0.7336 0.042 Uiso 1 1 calc R U . . .
H21B H 0.0093 0.4270 0.7545 0.042 Uiso 1 1 calc R U . . .
C22 C -0.0481(2) 0.2906(4) 0.68308(18) 0.0386(9) Uani 1 1 d . . . . .
H22A H -0.0919 0.3355 0.6500 0.046 Uiso 1 1 calc R U . . .
H22B H -0.0325 0.2294 0.6527 0.046 Uiso 1 1 calc R U . . .
C23 C -0.11670(18) 0.2741(3) 0.77845(16) 0.0237(7) Uani 1 1 d . . . . .
C24 C -0.1094(2) 0.0783(3) 0.79902(18) 0.0288(7) Uani 1 1 d . . . . .
H24 H -0.1164 0.0007 0.8175 0.035 Uiso 1 1 calc R U . . .
C25 C -0.0688(2) 0.1006(3) 0.7523(2) 0.0351(8) Uani 1 1 d . . . . .
H25 H -0.0425 0.0429 0.7325 0.042 Uiso 1 1 calc R U . . .
C26 C -0.1362(2) 0.4064(3) 0.7783(2) 0.0361(9) Uani 1 1 d . . . . .
H26A H -0.1440 0.4402 0.7289 0.054 Uiso 1 1 calc R U . . .
H26B H -0.0945 0.4496 0.8142 0.054 Uiso 1 1 calc R U . . .
H26C H -0.1827 0.4158 0.7916 0.054 Uiso 1 1 calc R U . . .
C27 C 0.1838(2) 0.4343(4) 0.6375(2) 0.0423(10) Uani 1 1 d . . . . .
H27A H 0.1948 0.3901 0.6842 0.063 Uiso 1 1 calc R U . . .
H27B H 0.1785 0.5210 0.6462 0.063 Uiso 1 1 calc R U . . .
H27C H 0.2255 0.4224 0.6170 0.063 Uiso 1 1 calc R U . . .
O9 O 0.64877(19) 0.3140(4) 0.32886(19) 0.0714(10) Uani 1 1 d . . . . .
N5 N 0.58780(19) 0.3291(3) 0.41666(18) 0.0458(8) Uani 1 1 d . . . . .
C28 C 0.6213(3) 0.3732(5) 0.3689(2) 0.0567(12) Uani 1 1 d . . . . .
H28 H 0.6240 0.4590 0.3657 0.068 Uiso 1 1 calc R U . . .
C29 C 0.5561(3) 0.4079(4) 0.4612(2) 0.0551(11) Uani 1 1 d . . . . .
H29A H 0.5581 0.4925 0.4460 0.083 Uiso 1 1 calc R U . . .
H29B H 0.5857 0.3992 0.5135 0.083 Uiso 1 1 calc R U . . .
H29C H 0.5032 0.3850 0.4540 0.083 Uiso 1 1 calc R U . . .
C30 C 0.5817(3) 0.1980(4) 0.4256(2) 0.0579(11) Uani 1 1 d . . . . .
H30A H 0.6010 0.1554 0.3902 0.087 Uiso 1 1 calc R U . . .
H30B H 0.5283 0.1762 0.4168 0.087 Uiso 1 1 calc R U . . .
H30C H 0.6116 0.1746 0.4759 0.087 Uiso 1 1 calc R U . . .
O10 O 0.6342(2) 0.7323(3) 0.1527(2) 0.0725(10) Uani 1 1 d . . . . .
N6 N 0.6824(3) 0.5393(4) 0.1575(2) 0.0635(11) Uani 1 1 d . . . . .
C31 C 0.6874(3) 0.6609(4) 0.1602(2) 0.0526(11) Uani 1 1 d . . . . .
H31 H 0.7364 0.6951 0.1687 0.063 Uiso 1 1 calc R U . . .
C32 C 0.7506(4) 0.4631(6) 0.1643(3) 0.097(2) Uani 1 1 d . . . . .
H32A H 0.7611 0.4121 0.2085 0.146 Uiso 1 1 calc R U . . .
H32B H 0.7944 0.5156 0.1686 0.146 Uiso 1 1 calc R U . . .
H32C H 0.7411 0.4116 0.1205 0.146 Uiso 1 1 calc R U . . .
C33 C 0.6094(4) 0.4775(7) 0.1452(5) 0.130(3) Uani 1 1 d . . . . .
H33A H 0.5698 0.5377 0.1425 0.194 Uiso 1 1 calc R U . . .
H33B H 0.6132 0.4215 0.1860 0.194 Uiso 1 1 calc R U . . .
H33C H 0.5965 0.4321 0.0987 0.194 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 2.016(2) . ?
Co1 O7 2.033(2) 4_666 ?
Co1 N1 2.044(2) . ?
Co1 O6 2.049(2) . ?
Co1 O1 2.051(2) . ?
Co1 Co2 2.9169(5) . ?
Co2 O5 2.033(2) . ?
Co2 O2 2.042(2) . ?
Co2 O3 2.046(2) . ?
Co2 O8 2.050(2) 4_666 ?
Co2 N4 2.061(2) 4_665 ?
O1 C1 1.255(3) . ?
O2 C1 1.259(4) . ?
O3 C2 1.247(4) . ?
O4 C2 1.254(4) . ?
O5 C6 1.264(4) . ?
O6 C6 1.254(4) . ?
O7 C14 1.264(4) . ?
O7 Co1 2.033(2) 4_565 ?
O8 C14 1.246(4) . ?
O8 Co2 2.050(2) 4_565 ?
N1 C17 1.331(4) . ?
N1 C19 1.376(4) . ?
N2 C17 1.349(4) . ?
N2 C18 1.372(4) . ?
N2 C20 1.467(4) . ?
N3 C23 1.348(4) . ?
N3 C25 1.391(5) . ?
N3 C22 1.469(4) . ?
N4 C23 1.326(4) . ?
N4 C24 1.389(4) . ?
N4 Co2 2.061(2) 4_566 ?
C1 C10 1.503(4) . ?
C2 C3 1.491(4) . ?
C3 C5 1.387(4) . ?
C3 C4 1.402(4) . ?
C4 C8 1.384(4) . ?
C4 H4A 0.9400 . ?
C5 C9 1.390(4) . ?
C5 H5A 0.9400 . ?
C6 C7 1.497(4) . ?
C7 C8 1.388(4) 1_565 ?
C7 C9 1.400(4) 1_565 ?
C8 C7 1.388(4) 1_545 ?
C8 H8A 0.9400 . ?
C9 C7 1.400(4) 1_545 ?
C9 H9A 0.9400 . ?
C10 C16 1.388(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9400 . ?
C13 C15 1.382(4) . ?
C13 C14 1.499(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C27 1.478(5) . ?
C18 C19 1.342(5) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.528(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.518(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C26 1.487(5) . ?
C24 C25 1.345(5) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
O9 C28 1.219(5) . ?
N5 C28 1.332(5) . ?
N5 C29 1.449(5) . ?
N5 C30 1.449(6) . ?
C28 H28 0.9400 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
O10 C31 1.222(5) . ?
N6 C31 1.330(6) . ?
N6 C33 1.452(7) . ?
N6 C32 1.474(6) . ?
C31 H31 0.9400 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?

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
O4 Co1 O7 88.66(11) . 4_666 ?
O4 Co1 N1 103.43(10) . . ?
O7 Co1 N1 106.59(10) 4_666 . ?
O4 Co1 O6 165.27(9) . . ?
O7 Co1 O6 88.15(11) 4_666 . ?
N1 Co1 O6 91.26(10) . . ?
O4 Co1 O1 88.85(11) . . ?
O7 Co1 O1 157.54(9) 4_666 . ?
N1 Co1 O1 95.70(10) . . ?
O6 Co1 O1 88.62(10) . . ?
O4 Co1 Co2 86.38(7) . . ?
O7 Co1 Co2 81.89(7) 4_666 . ?
N1 Co1 Co2 166.97(7) . . ?
O6 Co1 Co2 78.94(6) . . ?
O1 Co1 Co2 75.68(6) . . ?
O5 Co2 O2 90.62(10) . . ?
O5 Co2 O3 155.78(9) . . ?
O2 Co2 O3 86.65(10) . . ?
O5 Co2 O8 89.34(10) . 4_666 ?
O2 Co2 O8 163.66(9) . 4_666 ?
O3 Co2 O8 86.70(10) . 4_666 ?
O5 Co2 N4 93.86(10) . 4_665 ?
O2 Co2 N4 98.05(9) . 4_665 ?
O3 Co2 N4 110.35(10) . 4_665 ?
O8 Co2 N4 98.25(9) 4_666 4_665 ?
O5 Co2 Co1 82.01(6) . . ?
O2 Co2 Co1 85.01(6) . . ?
O3 Co2 Co1 73.78(7) . . ?
O8 Co2 Co1 78.81(6) 4_666 . ?
N4 Co2 Co1 174.92(7) 4_665 . ?
C1 O1 Co1 132.5(2) . . ?
C1 O2 Co2 120.66(19) . . ?
C2 O3 Co2 134.7(2) . . ?
C2 O4 Co1 119.7(2) . . ?
C6 O5 Co2 124.9(2) . . ?
C6 O6 Co1 128.4(2) . . ?
C14 O7 Co1 124.8(2) . 4_565 ?
C14 O8 Co2 128.5(2) . 4_565 ?
C17 N1 C19 106.1(3) . . ?
C17 N1 Co1 129.0(2) . . ?
C19 N1 Co1 123.9(2) . . ?
C17 N2 C18 107.9(3) . . ?
C17 N2 C20 126.5(3) . . ?
C18 N2 C20 125.5(3) . . ?
C23 N3 C25 107.5(3) . . ?
C23 N3 C22 126.0(3) . . ?
C25 N3 C22 125.6(3) . . ?
C23 N4 C24 106.0(3) . . ?
C23 N4 Co2 128.2(2) . 4_566 ?
C24 N4 Co2 125.4(2) . 4_566 ?
O1 C1 O2 125.3(3) . . ?
O1 C1 C10 116.9(3) . . ?
O2 C1 C10 117.8(2) . . ?
O3 C2 O4 125.1(3) . . ?
O3 C2 C3 117.2(3) . . ?
O4 C2 C3 117.6(3) . . ?
C5 C3 C4 119.5(3) . . ?
C5 C3 C2 120.8(3) . . ?
C4 C3 C2 119.7(3) . . ?
C8 C4 C3 119.8(3) . . ?
C8 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C3 C5 C9 120.6(3) . . ?
C3 C5 H5A 119.7 . . ?
C9 C5 H5A 119.7 . . ?
O6 C6 O5 125.7(3) . . ?
O6 C6 C7 116.6(3) . . ?
O5 C6 C7 117.6(3) . . ?
C8 C7 C9 119.5(3) 1_565 1_565 ?
C8 C7 C6 120.5(3) 1_565 . ?
C9 C7 C6 119.9(3) 1_565 . ?
C4 C8 C7 120.8(3) . 1_545 ?
C4 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 1_545 . ?
C5 C9 C7 119.8(3) . 1_545 ?
C5 C9 H9A 120.1 . . ?
C7 C9 H9A 120.1 1_545 . ?
C16 C10 C11 118.7(3) . . ?
C16 C10 C1 121.2(3) . . ?
C11 C10 C1 120.0(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C15 C13 C12 119.1(3) . . ?
C15 C13 C14 121.8(3) . . ?
C12 C13 C14 119.1(3) . . ?
O8 C14 O7 125.6(3) . . ?
O8 C14 C13 118.0(3) . . ?
O7 C14 C13 116.4(3) . . ?
C13 C15 C16 120.7(3) . . ?
C13 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C10 C16 C15 120.6(3) . . ?
C10 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N1 C17 N2 109.8(3) . . ?
N1 C17 C27 125.9(3) . . ?
N2 C17 C27 124.2(3) . . ?
C19 C18 N2 106.3(3) . . ?
C19 C18 H18 126.8 . . ?
N2 C18 H18 126.8 . . ?
C18 C19 N1 109.8(3) . . ?
C18 C19 H19 125.1 . . ?
N1 C19 H19 125.1 . . ?
N2 C20 C21 112.7(3) . . ?
N2 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N2 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 111.1(3) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N3 C22 C21 115.4(3) . . ?
N3 C22 H22A 108.4 . . ?
C21 C22 H22A 108.4 . . ?
N3 C22 H22B 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
N4 C23 N3 110.6(3) . . ?
N4 C23 C26 125.4(3) . . ?
N3 C23 C26 123.9(3) . . ?
C25 C24 N4 109.7(3) . . ?
C25 C24 H24 125.2 . . ?
N4 C24 H24 125.2 . . ?
C24 C25 N3 106.1(3) . . ?
C24 C25 H25 126.9 . . ?
N3 C25 H25 126.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 C27 H27A 109.5 . . ?
C17 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C17 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 N5 C29 122.3(4) . . ?
C28 N5 C30 120.4(4) . . ?
C29 N5 C30 117.3(3) . . ?
O9 C28 N5 126.7(5) . . ?
O9 C28 H28 116.6 . . ?
N5 C28 H28 116.6 . . ?
N5 C29 H29A 109.5 . . ?
N5 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N5 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 N6 C33 121.2(5) . . ?
C31 N6 C32 120.9(5) . . ?
C33 N6 C32 117.9(5) . . ?
O10 C31 N6 126.1(5) . . ?
O10 C31 H31 117.0 . . ?
N6 C31 H31 117.0 . . ?
N6 C32 H32A 109.5 . . ?
N6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N6 C33 H33A 109.5 . . ?
N6 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N6 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
Co1 O1 C1 O2 -12.0(5) . . . . ?
Co1 O1 C1 C10 168.0(2) . . . . ?
Co2 O2 C1 O1 11.4(5) . . . . ?
Co2 O2 C1 C10 -168.6(2) . . . . ?
Co2 O3 C2 O4 8.6(6) . . . . ?
Co2 O3 C2 C3 -169.8(2) . . . . ?
Co1 O4 C2 O3 -3.9(5) . . . . ?
Co1 O4 C2 C3 174.5(2) . . . . ?
O3 C2 C3 C5 -14.4(5) . . . . ?
O4 C2 C3 C5 167.2(3) . . . . ?
O3 C2 C3 C4 164.7(3) . . . . ?
O4 C2 C3 C4 -13.8(5) . . . . ?
C5 C3 C4 C8 0.7(5) . . . . ?
C2 C3 C4 C8 -178.4(3) . . . . ?
C4 C3 C5 C9 0.1(5) . . . . ?
C2 C3 C5 C9 179.2(3) . . . . ?
Co1 O6 C6 O5 -1.2(5) . . . . ?
Co1 O6 C6 C7 176.0(2) . . . . ?
Co2 O5 C6 O6 1.8(5) . . . . ?
Co2 O5 C6 C7 -175.3(2) . . . . ?
O6 C6 C7 C8 16.1(5) . . . 1_565 ?
O5 C6 C7 C8 -166.5(3) . . . 1_565 ?
O6 C6 C7 C9 -159.9(3) . . . 1_565 ?
O5 C6 C7 C9 17.5(5) . . . 1_565 ?
C3 C4 C8 C7 -1.1(5) . . . 1_545 ?
C3 C5 C9 C7 -0.5(5) . . . 1_545 ?
O1 C1 C10 C16 -8.7(5) . . . . ?
O2 C1 C10 C16 171.3(3) . . . . ?
O1 C1 C10 C11 170.4(3) . . . . ?
O2 C1 C10 C11 -9.5(5) . . . . ?
C16 C10 C11 C12 -0.9(5) . . . . ?
C1 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C15 0.9(5) . . . . ?
C11 C12 C13 C14 -177.8(3) . . . . ?
Co2 O8 C14 O7 5.5(5) 4_565 . . . ?
Co2 O8 C14 C13 -175.0(2) 4_565 . . . ?
Co1 O7 C14 O8 -7.9(5) 4_565 . . . ?
Co1 O7 C14 C13 172.6(2) 4_565 . . . ?
C15 C13 C14 O8 -169.2(3) . . . . ?
C12 C13 C14 O8 9.4(4) . . . . ?
C15 C13 C14 O7 10.3(5) . . . . ?
C12 C13 C14 O7 -171.1(3) . . . . ?
C12 C13 C15 C16 -0.4(5) . . . . ?
C14 C13 C15 C16 178.2(3) . . . . ?
C11 C10 C16 C15 1.4(5) . . . . ?
C1 C10 C16 C15 -179.5(3) . . . . ?
C13 C15 C16 C10 -0.7(5) . . . . ?
C19 N1 C17 N2 0.3(3) . . . . ?
Co1 N1 C17 N2 169.2(2) . . . . ?
C19 N1 C17 C27 -178.6(3) . . . . ?
Co1 N1 C17 C27 -9.7(5) . . . . ?
C18 N2 C17 N1 -0.6(4) . . . . ?
C20 N2 C17 N1 179.4(3) . . . . ?
C18 N2 C17 C27 178.4(3) . . . . ?
C20 N2 C17 C27 -1.6(5) . . . . ?
C17 N2 C18 C19 0.6(4) . . . . ?
C20 N2 C18 C19 -179.4(3) . . . . ?
N2 C18 C19 N1 -0.4(4) . . . . ?
C17 N1 C19 C18 0.0(4) . . . . ?
Co1 N1 C19 C18 -169.5(2) . . . . ?
C17 N2 C20 C21 -95.1(4) . . . . ?
C18 N2 C20 C21 84.9(4) . . . . ?
N2 C20 C21 C22 -62.4(4) . . . . ?
C23 N3 C22 C21 76.2(5) . . . . ?
C25 N3 C22 C21 -115.8(4) . . . . ?
C20 C21 C22 N3 -163.4(3) . . . . ?
C24 N4 C23 N3 -0.5(4) . . . . ?
Co2 N4 C23 N3 -173.6(2) 4_566 . . . ?
C24 N4 C23 C26 179.0(3) . . . . ?
Co2 N4 C23 C26 5.8(5) 4_566 . . . ?
C25 N3 C23 N4 0.4(4) . . . . ?
C22 N3 C23 N4 170.2(3) . . . . ?
C25 N3 C23 C26 -179.0(3) . . . . ?
C22 N3 C23 C26 -9.3(5) . . . . ?
C23 N4 C24 C25 0.4(4) . . . . ?
Co2 N4 C24 C25 173.8(2) 4_566 . . . ?
N4 C24 C25 N3 -0.1(4) . . . . ?
C23 N3 C25 C24 -0.2(4) . . . . ?
C22 N3 C25 C24 -170.0(3) . . . . ?
C29 N5 C28 O9 -179.3(4) . . . . ?
C30 N5 C28 O9 0.5(7) . . . . ?
C33 N6 C31 O10 -0.4(8) . . . . ?
C32 N6 C31 O10 177.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20A O1 0.98 2.60 3.491(4) 151 3_566
C21 H21A O9 0.98 2.54 3.422(5) 150 4_566
C26 H26C O3 0.97 2.39 3.234(4) 145 4_566
C27 H27C O7 0.97 2.44 3.300(4) 147 4_666
C31 H31 O9 0.94 2.46 3.390(6) 168 2_655

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

