# 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1527997'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 Cl Cu4 N12 O16'
_chemical_formula_weight         1178.34

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   29.8816(12)
_cell_length_b                   7.7255(3)
_cell_length_c                   21.4941(9)
_cell_angle_alpha                90
_cell_angle_beta                 117.245(2)
_cell_angle_gamma                90
_cell_volume                     4411.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4024
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             2372
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.048
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14470
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         25.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4083
_reflns_number_gt                3488
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0504P)²+10.7404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4083
_refine_ls_number_parameters     337
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.109
_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
C1 C 0.19489(13) 0.9213(4) 0.34786(16) 0.0236(7) Uani 1 1 d . . . . .
C2 C 0.17411(13) 0.8693(4) 0.27243(16) 0.0257(7) Uani 1 1 d . . . . .
C3 C 0.19539(14) 0.9318(5) 0.23137(17) 0.0276(8) Uani 1 1 d . . . . .
H3 H 0.2238 1.0017 0.2512 0.033 Uiso 1 1 calc R U . . .
C4 C 0.17406(15) 0.8896(5) 0.16035(18) 0.0315(8) Uani 1 1 d . . . . .
C5 C 0.13186(16) 0.7853(5) 0.13164(19) 0.0406(10) Uani 1 1 d . . . . .
H5 H 0.1173 0.7580 0.0843 0.049 Uiso 1 1 calc R U . . .
C6 C 0.11089(17) 0.7210(6) 0.17263(19) 0.0443(11) Uani 1 1 d . . . . .
H6 H 0.0828 0.6495 0.1530 0.053 Uiso 1 1 calc R U . . .
C7 C 0.13198(15) 0.7638(5) 0.24269(19) 0.0368(9) Uani 1 1 d . . . . .
H7 H 0.1178 0.7214 0.2702 0.044 Uiso 1 1 calc R U . . .
C8 C 0.07130(14) 1.0717(6) 0.4394(2) 0.0398(10) Uani 1 1 d . . . . .
H8 H 0.0852 1.1310 0.4818 0.048 Uiso 1 1 calc R U . . .
C9 C 0.06310(17) 0.9157(8) 0.3547(2) 0.0718(18) Uani 1 1 d . . . . .
H9 H 0.0707 0.8457 0.3256 0.086 Uiso 1 1 calc R U . . .
C10 C 0.01631(18) 0.9607(9) 0.3424(3) 0.080(2) Uani 1 1 d . . . . .
H10 H -0.0138 0.9278 0.3046 0.096 Uiso 1 1 calc R U . . .
C11 C -0.01537(14) 1.1456(5) 0.41045(19) 0.0332(8) Uani 1 1 d . . . . .
C12 C -0.06411(14) 1.1669(6) 0.3607(2) 0.0405(10) Uani 1 1 d . . . . .
H12 H -0.0749 1.1279 0.3151 0.049 Uiso 1 1 calc R U . . .
C13 C -0.09615(14) 1.2471(5) 0.3800(2) 0.0387(9) Uani 1 1 d . . . . .
H13 H -0.1298 1.2650 0.3486 0.046 Uiso 1 1 calc R U . . .
C14 C -0.07641(13) 1.3006(5) 0.44866(19) 0.0299(8) Uani 1 1 d . . . . .
N6 N -0.02899(13) 1.2810(6) 0.49490(18) 0.0540(11) Uani 1 1 d . . . . .
N5 N 0.00245(13) 1.1992(6) 0.47511(17) 0.0559(11) Uani 1 1 d . . . . .
Cl1 Cl 0.5000 0.0418(2) 0.7500 0.0645(5) Uani 1 2 d DS TU P . .
Cu1 Cu 0.17192(2) 0.96548(5) 0.46626(2) 0.02285(13) Uani 1 1 d . . . . .
Cu2 Cu 0.26698(2) 1.10955(5) 0.46874(2) 0.02176(13) Uani 1 1 d . . . . .
N1 N 0.09766(11) 0.9869(4) 0.41554(15) 0.0307(7) Uani 1 1 d . . . . .
N2 N 0.02207(11) 1.0642(4) 0.39670(16) 0.0343(7) Uani 1 1 d . . . . .
O1 O 0.23531(9) 1.0062(3) 0.37419(12) 0.0295(6) Uani 1 1 d . . . . .
O2 O 0.16966(9) 0.8762(3) 0.37868(11) 0.0278(5) Uani 1 1 d . . . . .
O3 O 0.20492(9) 1.2254(3) 0.45364(12) 0.0233(5) Uani 1 1 d . . . . .
H1W H 0.1906(15) 1.256(5) 0.417(2) 0.028 Uiso 1 1 d . U . . .
O4 O 0.24083(9) 0.8901(3) 0.51753(11) 0.0237(5) Uani 1 1 d D . . . .
H2W H 0.2498(14) 0.893(5) 0.5585(10) 0.028 Uiso 1 1 d D U . . .
O7A O 0.4836(8) 0.143(2) 0.6933(8) 0.139(6) Uani 0.413(14) 1 d D U P A 1
O8A O 0.4652(6) -0.082(2) 0.7348(11) 0.178(6) Uani 0.413(14) 1 d D U P A 1
O7B O 0.4586(5) 0.129(2) 0.7041(8) 0.176(6) Uani 0.587(14) 1 d D U P A 2
O8B O 0.4837(6) -0.041(2) 0.7909(7) 0.177(5) Uani 0.587(14) 1 d D U P A 2
C15 C 0.19538(15) 0.9680(5) 0.11461(18) 0.0331(8) Uani 1 1 d . . . . .
O5 O 0.16676(11) 0.9580(4) 0.05002(13) 0.0457(8) Uani 1 1 d . . . . .
O6 O 0.23708(13) 1.0383(5) 0.14149(14) 0.0622(10) Uani 1 1 d . . . . .
N4 N -0.10507(11) 1.3877(4) 0.47648(15) 0.0303(7) Uani 1 1 d . . . . .
C16 C -0.15463(13) 1.4251(5) 0.44471(19) 0.0289(8) Uani 1 1 d . . . . .
H16 H -0.1767 1.3953 0.3988 0.035 Uiso 1 1 calc R U . . .
C18 C -0.08532(16) 1.4512(6) 0.5438(2) 0.0497(12) Uani 1 1 d . . . . .
H18 H -0.0521 1.4440 0.5783 0.060 Uiso 1 1 calc R U . . .
N3 N -0.16756(11) 1.5091(4) 0.48691(15) 0.0298(7) Uani 1 1 d . . . . .
C17 C -0.12399(16) 1.5258(6) 0.5491(2) 0.0496(12) Uani 1 1 d . . . . .
H17 H -0.1217 1.5807 0.5889 0.059 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
C1 O1 1.258(4) . ?
C1 O2 1.260(4) . ?
C1 C2 1.501(4) . ?
C2 C7 1.386(5) . ?
C2 C3 1.389(5) . ?
C3 C4 1.397(5) . ?
C4 C5 1.381(5) . ?
C4 C15 1.521(5) . ?
C5 C6 1.386(5) . ?
C6 C7 1.380(5) . ?
C8 N1 1.298(5) . ?
C8 N2 1.332(5) . ?
C9 C10 1.345(6) . ?
C9 N1 1.358(5) . ?
C10 N2 1.359(5) . ?
C11 N5 1.308(5) . ?
C11 C12 1.366(5) . ?
C11 N2 1.427(4) . ?
C12 C13 1.356(5) . ?
C13 C14 1.378(5) . ?
C14 N6 1.315(5) . ?
C14 N4 1.419(4) . ?
N6 N5 1.352(4) . ?
Cl1 O7A 1.338(7) 2_656 ?
Cl1 O7A 1.338(7) . ?
Cl1 O8B 1.346(7) . ?
Cl1 O8B 1.346(7) 2_656 ?
Cl1 O7B 1.356(7) . ?
Cl1 O7B 1.356(7) 2_656 ?
Cl1 O8A 1.341(7) . ?
Cl1 O8A 1.341(7) 2_656 ?
Cu1 O4 1.928(2) . ?
Cu1 O5 1.967(2) 6_576 ?
Cu1 O2 1.977(2) . ?
Cu1 N1 1.981(3) . ?
Cu1 O3 2.307(2) . ?
Cu1 Cu2 3.0285(6) . ?
Cu2 O3 1.948(2) . ?
Cu2 O3 1.957(2) 7_576 ?
Cu2 N3 1.970(3) 3_545 ?
Cu2 O1 1.975(2) . ?
Cu2 O4 2.310(2) . ?
Cu2 Cu2 2.9653(7) 7_576 ?
O3 Cu2 1.957(2) 7_576 ?
C15 O6 1.234(5) . ?
C15 O5 1.256(4) . ?
O5 Cu1 1.967(2) 6_575 ?
N4 C16 1.348(4) . ?
N4 C18 1.378(5) . ?
C16 N3 1.309(4) . ?
C18 C17 1.342(6) . ?
N3 C17 1.380(5) . ?
N3 Cu2 1.970(3) 3_455 ?

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 C1 O2 126.2(3) . . ?
O1 C1 C2 117.6(3) . . ?
O2 C1 C2 116.3(3) . . ?
C7 C2 C3 119.6(3) . . ?
C7 C2 C1 119.7(3) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 120.0(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 C15 120.7(3) . . ?
C3 C4 C15 119.8(3) . . ?
C4 C5 C6 120.7(3) . . ?
C7 C6 C5 119.6(4) . . ?
C6 C7 C2 120.6(3) . . ?
N1 C8 N2 112.6(3) . . ?
C10 C9 N1 110.4(4) . . ?
C9 C10 N2 105.8(4) . . ?
N5 C11 C12 124.3(3) . . ?
N5 C11 N2 112.5(3) . . ?
C12 C11 N2 123.2(3) . . ?
C13 C12 C11 117.7(4) . . ?
C12 C13 C14 116.7(3) . . ?
N6 C14 C13 124.1(3) . . ?
N6 C14 N4 112.7(3) . . ?
C13 C14 N4 123.3(3) . . ?
C14 N6 N5 118.6(3) . . ?
C11 N5 N6 118.6(3) . . ?
O7A Cl1 O7A 109(2) 2_656 . ?
O8B Cl1 O8B 123.4(15) . 2_656 ?
O8B Cl1 O7B 103.3(9) . . ?
O8B Cl1 O7B 104.0(10) 2_656 . ?
O8B Cl1 O7B 104.0(10) . 2_656 ?
O8B Cl1 O7B 103.3(9) 2_656 2_656 ?
O7B Cl1 O7B 120.3(15) . 2_656 ?
O7A Cl1 O8A 124.1(15) 2_656 . ?
O7A Cl1 O8A 106.0(9) . . ?
O7A Cl1 O8A 106.0(9) 2_656 2_656 ?
O7A Cl1 O8A 124.1(15) . 2_656 ?
O8A Cl1 O8A 88.5(19) . 2_656 ?
O4 Cu1 O5 94.49(10) . 6_576 ?
O4 Cu1 O2 90.04(10) . . ?
O5 Cu1 O2 173.57(12) 6_576 . ?
O4 Cu1 N1 166.91(12) . . ?
O5 Cu1 N1 86.63(11) 6_576 . ?
O2 Cu1 N1 87.92(11) . . ?
O4 Cu1 O3 85.88(9) . . ?
O5 Cu1 O3 93.60(11) 6_576 . ?
O2 Cu1 O3 91.26(9) . . ?
N1 Cu1 O3 107.09(11) . . ?
O4 Cu1 Cu2 49.70(7) . . ?
O5 Cu1 Cu2 109.83(10) 6_576 . ?
O2 Cu1 Cu2 76.58(7) . . ?
N1 Cu1 Cu2 141.65(9) . . ?
O3 Cu1 Cu2 40.03(6) . . ?
O3 Cu2 O3 81.19(10) . 7_576 ?
O3 Cu2 N3 175.63(11) . 3_545 ?
O3 Cu2 N3 95.05(11) 7_576 3_545 ?
O3 Cu2 O1 92.47(10) . . ?
O3 Cu2 O1 163.07(10) 7_576 . ?
N3 Cu2 O1 90.54(11) 3_545 . ?
O3 Cu2 O4 85.35(9) . . ?
O3 Cu2 O4 101.15(9) 7_576 . ?
N3 Cu2 O4 97.61(10) 3_545 . ?
O1 Cu2 O4 93.91(9) . . ?
O3 Cu2 Cu2 40.71(7) . 7_576 ?
O3 Cu2 Cu2 40.48(7) 7_576 7_576 ?
N3 Cu2 Cu2 135.49(9) 3_545 7_576 ?
O1 Cu2 Cu2 131.28(8) . 7_576 ?
O4 Cu2 Cu2 94.27(6) . 7_576 ?
O3 Cu2 Cu1 49.63(7) . . ?
O3 Cu2 Cu1 106.70(7) 7_576 . ?
N3 Cu2 Cu1 134.18(9) 3_545 . ?
O1 Cu2 Cu1 80.19(7) . . ?
O4 Cu2 Cu1 39.53(6) . . ?
Cu2 Cu2 Cu1 76.357(17) 7_576 . ?
C8 N1 C9 104.7(3) . . ?
C8 N1 Cu1 123.7(3) . . ?
C9 N1 Cu1 131.5(3) . . ?
C8 N2 C10 106.5(3) . . ?
C8 N2 C11 124.1(3) . . ?
C10 N2 C11 129.3(3) . . ?
C1 O1 Cu2 125.6(2) . . ?
C1 O2 Cu1 129.5(2) . . ?
Cu2 O3 Cu2 98.81(10) . 7_576 ?
Cu2 O3 Cu1 90.34(9) . . ?
Cu2 O3 Cu1 120.42(11) 7_576 . ?
Cu1 O4 Cu2 90.77(9) . . ?
O6 C15 O5 125.1(3) . . ?
O6 C15 C4 120.3(3) . . ?
O5 C15 C4 114.5(3) . . ?
C15 O5 Cu1 134.0(2) . 6_575 ?
C16 N4 C18 107.4(3) . . ?
C16 N4 C14 128.6(3) . . ?
C18 N4 C14 124.1(3) . . ?
N3 C16 N4 111.1(3) . . ?
C17 C18 N4 105.7(4) . . ?
C16 N3 C17 105.7(3) . . ?
C16 N3 Cu2 129.7(3) . 3_455 ?
C17 N3 Cu2 124.5(2) . 3_455 ?
C18 C17 N3 110.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 174.8(3) . . . . ?
O2 C1 C2 C7 -5.7(5) . . . . ?
O1 C1 C2 C3 -8.0(5) . . . . ?
O2 C1 C2 C3 171.5(3) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 -176.6(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C15 175.9(3) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C15 C4 C5 C6 -176.7(4) . . . . ?
C4 C5 C6 C7 1.0(7) . . . . ?
C5 C6 C7 C2 -0.5(7) . . . . ?
C3 C2 C7 C6 -0.3(6) . . . . ?
C1 C2 C7 C6 177.0(4) . . . . ?
N1 C9 C10 N2 0.7(8) . . . . ?
N5 C11 C12 C13 -0.9(7) . . . . ?
N2 C11 C12 C13 -179.7(4) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 N6 1.2(6) . . . . ?
C12 C13 C14 N4 179.4(4) . . . . ?
C13 C14 N6 N5 -1.9(7) . . . . ?
N4 C14 N6 N5 179.7(4) . . . . ?
C12 C11 N5 N6 0.2(7) . . . . ?
N2 C11 N5 N6 179.1(4) . . . . ?
C14 N6 N5 C11 1.2(7) . . . . ?
N2 C8 N1 C9 -2.1(5) . . . . ?
N2 C8 N1 Cu1 -178.6(3) . . . . ?
C10 C9 N1 C8 0.8(7) . . . . ?
C10 C9 N1 Cu1 176.8(4) . . . . ?
N1 C8 N2 C10 2.6(6) . . . . ?
N1 C8 N2 C11 179.8(4) . . . . ?
C9 C10 N2 C8 -1.9(7) . . . . ?
C9 C10 N2 C11 -178.9(5) . . . . ?
N5 C11 N2 C8 -12.7(6) . . . . ?
C12 C11 N2 C8 166.2(4) . . . . ?
N5 C11 N2 C10 163.8(5) . . . . ?
C12 C11 N2 C10 -17.3(7) . . . . ?
O2 C1 O1 Cu2 -5.8(5) . . . . ?
C2 C1 O1 Cu2 173.7(2) . . . . ?
O1 C1 O2 Cu1 17.7(5) . . . . ?
C2 C1 O2 Cu1 -161.8(2) . . . . ?
C5 C4 C15 O6 -168.8(4) . . . . ?
C3 C4 C15 O6 15.2(6) . . . . ?
C5 C4 C15 O5 13.0(6) . . . . ?
C3 C4 C15 O5 -163.0(4) . . . . ?
O6 C15 O5 Cu1 1.2(7) . . . 6_575 ?
C4 C15 O5 Cu1 179.3(3) . . . 6_575 ?
N6 C14 N4 C16 -178.0(4) . . . . ?
C13 C14 N4 C16 3.6(6) . . . . ?
N6 C14 N4 C18 2.4(6) . . . . ?
C13 C14 N4 C18 -176.0(4) . . . . ?
C18 N4 C16 N3 0.5(5) . . . . ?
C14 N4 C16 N3 -179.1(3) . . . . ?
C16 N4 C18 C17 -0.6(5) . . . . ?
C14 N4 C18 C17 179.1(4) . . . . ?
N4 C16 N3 C17 -0.2(4) . . . . ?
N4 C16 N3 Cu2 175.9(2) . . . 3_455 ?
N4 C18 C17 N3 0.5(6) . . . . ?
C16 N3 C17 C18 -0.2(5) . . . . ?
Cu2 N3 C17 C18 -176.6(3) 3_455 . . . ?

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
C8 H8 O5 0.93 2.30 2.762(5) 110.2 6_576
C9 H9 O8A 0.93 2.39 3.09(2) 132.3 7_556
O4 H2W O6 0.796(18) 2.06(2) 2.773(3) 150(4) 6_576
C18 H18 O8B 0.93 2.61 3.459(16) 151.5 4_566
C17 H17 O7B 0.93 2.57 3.211(16) 126.6 3_465

_refine_diff_density_max         1.304
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.085



####################################################################### 
# 
# 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 1527998'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14.50 N6 Ni O5.25'
_chemical_formula_weight         457.57

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.4549(3)
_cell_length_b                   9.6723(4)
_cell_length_c                   12.4874(6)
_cell_angle_alpha                111.4130(10)
_cell_angle_beta                 90.1010(10)
_cell_angle_gamma                101.5080(10)
_cell_volume                     928.48(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3879
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.22

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             469
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.093
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6135
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         25.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3360
_reflns_number_gt                3210
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0042P)²+5.6224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     316
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.279
_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
C1 C 0.1917(6) 0.2093(6) 0.1459(5) 0.0286(12) Uani 1 1 d . . . . .
H1 H 0.2450 0.2245 0.2158 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0223(8) 0.2113(6) 0.0200(5) 0.0342(13) Uani 1 1 d . . . . .
H2 H -0.0669 0.2289 -0.0127 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1340(8) 0.1389(7) -0.0401(5) 0.0420(15) Uani 1 1 d . . . . .
H3 H 0.1368 0.0988 -0.1198 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3522(9) 0.0583(11) 0.0018(7) 0.027(2) Uani 0.5 1 d G U P A -1
C5 C 0.4199(11) 0.0277(12) -0.1035(6) 0.032(3) Uani 0.5 1 d G U P A -1
H5 H 0.3773 0.0540 -0.1603 0.039 Uiso 0.5 1 calc R U P A -1
C6 C 0.5513(12) -0.0422(11) -0.1240(5) 0.033(3) Uani 0.5 1 d G U P A -1
H6 H 0.5967 -0.0626 -0.1945 0.039 Uiso 0.5 1 calc R U P A -1
C7 C 0.6150(9) -0.0816(10) -0.0391(6) 0.022(2) Uani 0.5 1 d G U P A -1
N3 N 0.5473(9) -0.0510(9) 0.0662(6) 0.035(2) Uani 0.5 1 d G . P A -1
N4 N 0.4158(9) 0.0189(9) 0.0867(6) 0.039(3) Uani 0.5 1 d G . P A -1
C8 C 0.1909(7) 0.6468(6) 0.3681(5) 0.0338(13) Uani 1 1 d . . . . .
H8 H 0.2253 0.6155 0.4246 0.041 Uiso 1 1 calc R U . . .
C9 C 0.0592(7) 0.6551(7) 0.2247(6) 0.0367(13) Uani 1 1 d . . . . .
H9 H -0.0172 0.6277 0.1627 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1761(8) 0.7830(7) 0.2624(7) 0.0490(18) Uani 1 1 d . . . . .
H10 H 0.1957 0.8592 0.2323 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3753(10) 0.8936(9) 0.4015(6) 0.037(3) Uani 0.5 1 d G . P B -1
N7 N 0.4455(11) 1.0195(10) 0.3759(5) 0.073(5) Uani 0.5 1 d G . P B -1
N8 N 0.5641(10) 1.1341(9) 0.4528(7) 0.052(3) Uani 0.5 1 d G . P B -1
C14 C 0.6125(10) 1.1229(10) 0.5552(6) 0.019(2) Uani 0.5 1 d G U P B -1
C13 C 0.5423(11) 0.9970(11) 0.5808(5) 0.033(3) Uani 0.5 1 d G . P B -1
H13 H 0.5747 0.9895 0.6493 0.040 Uiso 0.5 1 calc R U P B -1
C12 C 0.4237(11) 0.8824(10) 0.5039(7) 0.028(3) Uani 0.5 1 d G U P B -1
H12 H 0.3767 0.7982 0.5210 0.033 Uiso 0.5 1 calc R U P B -1
C15 C -0.0312(6) 0.1861(5) 0.3679(4) 0.0222(10) Uani 1 1 d . . . . .
C16 C -0.0129(6) 0.0892(6) 0.4358(4) 0.0227(10) Uani 1 1 d . . . . .
C17 C -0.1232(6) -0.0483(6) 0.4123(4) 0.0255(11) Uani 1 1 d . . . . .
H17 H -0.2054 -0.0807 0.3534 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1107(6) 0.1367(6) 0.5237(4) 0.0258(11) Uani 1 1 d . . . . .
H18 H 0.1850 0.2281 0.5394 0.031 Uiso 1 1 calc R U . . .
C19 C -0.3565(7) 0.4343(7) 0.1825(5) 0.0335(13) Uani 1 1 d . . . . .
C20 C -0.4313(6) 0.4670(6) 0.0870(5) 0.0273(11) Uani 1 1 d . . . . .
C21 C -0.3637(7) 0.4394(8) -0.0173(5) 0.0390(15) Uani 1 1 d . . . . .
H21 H -0.2718 0.3982 -0.0298 0.047 Uiso 1 1 calc R U . . .
C22 C -0.5683(7) 0.5273(8) 0.1034(5) 0.0429(16) Uani 1 1 d . . . . .
H22 H -0.6153 0.5458 0.1731 0.052 Uiso 1 1 calc R U . . .
N1 N 0.0595(5) 0.2551(5) 0.1366(4) 0.0245(9) Uani 1 1 d . . . . .
N2 N 0.2422(6) 0.1367(5) 0.0409(4) 0.0346(11) Uani 1 1 d . . . . .
N5 N 0.0701(5) 0.5708(5) 0.2922(4) 0.0242(9) Uani 1 1 d . . . . .
N6 N 0.2608(6) 0.7775(5) 0.3551(5) 0.0419(13) Uani 1 1 d . . . . .
Ni1 Ni -0.06867(7) 0.36138(7) 0.27169(5) 0.01794(18) Uani 1 1 d . . . . .
O1 O 0.0699(4) 0.3110(4) 0.3899(3) 0.0264(8) Uani 1 1 d . . . . .
O2 O -0.1463(4) 0.1447(4) 0.2926(3) 0.0267(8) Uani 1 1 d . . . . .
O3 O -0.2039(5) 0.4478(4) 0.4104(3) 0.0281(8) Uani 1 1 d D . . . .
H1W H -0.292(4) 0.454(8) 0.386(5) 0.042 Uiso 1 1 d D U . . .
H2W H -0.166(7) 0.530(4) 0.465(4) 0.042 Uiso 1 1 d D U . . .
O4 O -0.2359(4) 0.3734(4) 0.1603(3) 0.0280(8) Uani 1 1 d . . . . .
O5 O -0.4193(7) 0.4687(8) 0.2755(4) 0.080(2) Uani 1 1 d . . . . .
O6 O 0.418(2) 0.305(3) 0.394(2) 0.073(7) Uani 0.25 1 d D . P . .
H3W H 0.5034 0.2283 0.4016 0.110 Uiso 0.25 1 d DR U P . .
H4W H 0.4603 0.3403 0.3464 0.110 Uiso 0.25 1 d DR U P . .


_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
C1 N1 1.301(7) . ?
C1 N2 1.359(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(8) . ?
C2 N1 1.375(7) . ?
C2 H2 0.9300 . ?
C3 N2 1.371(8) . ?
C3 H3 0.9300 . ?
C4 N2 1.300(9) . ?
C4 C5 1.3900 . ?
C4 N4 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 N3 1.3900 . ?
N3 N4 1.3900 . ?
C8 N5 1.293(7) . ?
C8 N6 1.351(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(9) . ?
C9 N5 1.385(7) . ?
C9 H9 0.9300 . ?
C10 N6 1.384(9) . ?
C10 H10 0.9300 . ?
C11 N6 1.274(9) . ?
C11 N7 1.3900 . ?
C11 C12 1.3900 . ?
N7 N8 1.3900 . ?
N8 C14 1.3900 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C15 O2 1.248(6) . ?
C15 O1 1.269(6) . ?
C15 C16 1.503(6) . ?
C15 Ni1 2.473(5) . ?
C16 C17 1.393(7) . ?
C16 C18 1.395(7) . ?
C17 C18 1.385(7) 2_556 ?
C17 H17 0.9300 . ?
C18 C17 1.384(7) 2_556 ?
C18 H18 0.9300 . ?
C19 O5 1.238(7) . ?
C19 O4 1.259(6) . ?
C19 C20 1.509(7) . ?
C20 C21 1.379(8) . ?
C20 C22 1.381(7) . ?
C21 C22 1.384(8) 2_465 ?
C21 H21 0.9300 . ?
C22 C21 1.384(8) 2_465 ?
C22 H22 0.9300 . ?
N1 Ni1 2.065(4) . ?
N5 Ni1 2.053(4) . ?
Ni1 O4 2.031(3) . ?
Ni1 O3 2.083(4) . ?
Ni1 O1 2.130(3) . ?
Ni1 O2 2.178(3) . ?
O3 H1W 0.83(2) . ?
O3 H2W 0.84(2) . ?
O6 H3W 1.1551 . ?
O6 H4W 0.8373 . ?

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 C1 N2 111.6(5) . . ?
N1 C1 H1 124.2 . . ?
N2 C1 H1 124.2 . . ?
C3 C2 N1 110.2(5) . . ?
C3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
C2 C3 N2 105.8(5) . . ?
C2 C3 H3 127.1 . . ?
N2 C3 H3 127.1 . . ?
N2 C4 C5 128.5(5) . . ?
N2 C4 N4 111.1(5) . . ?
C5 C4 N4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N3 C7 C6 120.0 . . ?
N4 N3 C7 120.0 . . ?
N3 N4 C4 120.0 . . ?
N5 C8 N6 111.5(5) . . ?
N5 C8 H8 124.2 . . ?
N6 C8 H8 124.2 . . ?
C10 C9 N5 109.6(6) . . ?
C10 C9 H9 125.2 . . ?
N5 C9 H9 125.2 . . ?
C9 C10 N6 105.7(5) . . ?
C9 C10 H10 127.2 . . ?
N6 C10 H10 127.2 . . ?
N6 C11 N7 135.5(6) . . ?
N6 C11 C12 104.4(6) . . ?
N7 C11 C12 120.0 . . ?
N8 N7 C11 120.0 . . ?
N7 N8 C14 120.0 . . ?
N8 C14 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O2 C15 O1 121.0(4) . . ?
O2 C15 C16 120.0(4) . . ?
O1 C15 C16 119.0(4) . . ?
O2 C15 Ni1 61.6(2) . . ?
O1 C15 Ni1 59.5(2) . . ?
C16 C15 Ni1 175.0(3) . . ?
C17 C16 C18 119.6(5) . . ?
C17 C16 C15 119.6(4) . . ?
C18 C16 C15 120.8(5) . . ?
C18 C17 C16 120.3(5) 2_556 . ?
C18 C17 H17 119.9 2_556 . ?
C16 C17 H17 119.9 . . ?
C17 C18 C16 120.1(5) 2_556 . ?
C17 C18 H18 119.9 2_556 . ?
C16 C18 H18 119.9 . . ?
O5 C19 O4 125.7(5) . . ?
O5 C19 C20 117.3(5) . . ?
O4 C19 C20 116.9(5) . . ?
C21 C20 C22 118.8(5) . . ?
C21 C20 C19 121.0(5) . . ?
C22 C20 C19 120.2(5) . . ?
C20 C21 C22 120.4(5) . 2_465 ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 2_465 . ?
C20 C22 C21 120.8(5) . 2_465 ?
C20 C22 H22 119.6 . . ?
C21 C22 H22 119.6 2_465 . ?
C1 N1 C2 105.6(4) . . ?
C1 N1 Ni1 125.7(4) . . ?
C2 N1 Ni1 128.6(4) . . ?
C4 N2 C1 136.4(6) . . ?
C4 N2 C3 116.4(6) . . ?
C1 N2 C3 106.8(5) . . ?
C8 N5 C9 106.2(5) . . ?
C8 N5 Ni1 126.4(4) . . ?
C9 N5 Ni1 127.3(4) . . ?
C11 N6 C8 140.1(7) . . ?
C11 N6 C10 113.0(6) . . ?
C8 N6 C10 107.0(5) . . ?
O4 Ni1 N5 92.94(16) . . ?
O4 Ni1 N1 90.97(16) . . ?
N5 Ni1 N1 91.26(17) . . ?
O4 Ni1 O3 91.12(15) . . ?
N5 Ni1 O3 94.03(16) . . ?
N1 Ni1 O3 174.20(16) . . ?
O4 Ni1 O1 168.25(15) . . ?
N5 Ni1 O1 98.47(15) . . ?
N1 Ni1 O1 91.56(15) . . ?
O3 Ni1 O1 85.32(14) . . ?
O4 Ni1 O2 107.51(14) . . ?
N5 Ni1 O2 159.55(15) . . ?
N1 Ni1 O2 88.39(15) . . ?
O3 Ni1 O2 85.82(15) . . ?
O1 Ni1 O2 61.11(13) . . ?
O4 Ni1 C15 137.61(16) . . ?
N5 Ni1 C15 129.32(17) . . ?
N1 Ni1 C15 91.16(16) . . ?
O3 Ni1 C15 83.65(15) . . ?
O1 Ni1 C15 30.86(15) . . ?
O2 Ni1 C15 30.29(15) . . ?
C15 O1 Ni1 89.7(3) . . ?
C15 O2 Ni1 88.1(3) . . ?
Ni1 O3 H1W 109(5) . . ?
Ni1 O3 H2W 121(5) . . ?
H1W O3 H2W 107(6) . . ?
C19 O4 Ni1 128.7(4) . . ?
H3W O6 H4W 103.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.5(7) . . . . ?
N2 C4 C5 C6 171.7(8) . . . . ?
N4 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 N3 0.0 . . . . ?
C6 C7 N3 N4 0.0 . . . . ?
C7 N3 N4 C4 0.0 . . . . ?
N2 C4 N4 N3 -173.1(7) . . . . ?
C5 C4 N4 N3 0.0 . . . . ?
N5 C9 C10 N6 0.0(7) . . . . ?
N6 C11 N7 N8 174.8(9) . . . . ?
C12 C11 N7 N8 0.0 . . . . ?
C11 N7 N8 C14 0.0 . . . . ?
N7 N8 C14 C13 0.0 . . . . ?
N8 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
N6 C11 C12 C13 -176.3(6) . . . . ?
N7 C11 C12 C13 0.0 . . . . ?
O2 C15 C16 C17 1.3(7) . . . . ?
O1 C15 C16 C17 -180.0(5) . . . . ?
O2 C15 C16 C18 -177.2(5) . . . . ?
O1 C15 C16 C18 1.6(7) . . . . ?
C18 C16 C17 C18 0.4(8) . . . 2_556 ?
C15 C16 C17 C18 -178.1(5) . . . 2_556 ?
C17 C16 C18 C17 -0.4(8) . . . 2_556 ?
C15 C16 C18 C17 178.1(5) . . . 2_556 ?
O5 C19 C20 C21 176.6(7) . . . . ?
O4 C19 C20 C21 -3.8(9) . . . . ?
O5 C19 C20 C22 -2.5(10) . . . . ?
O4 C19 C20 C22 177.0(6) . . . . ?
C22 C20 C21 C22 0.4(11) . . . 2_465 ?
C19 C20 C21 C22 -178.8(6) . . . 2_465 ?
C21 C20 C22 C21 -0.4(11) . . . 2_465 ?
C19 C20 C22 C21 178.8(6) . . . 2_465 ?
N2 C1 N1 C2 -0.4(6) . . . . ?
N2 C1 N1 Ni1 176.9(4) . . . . ?
C3 C2 N1 C1 0.0(7) . . . . ?
C3 C2 N1 Ni1 -177.2(4) . . . . ?
C5 C4 N2 C1 -159.6(6) . . . . ?
N4 C4 N2 C1 12.7(10) . . . . ?
C5 C4 N2 C3 28.9(9) . . . . ?
N4 C4 N2 C3 -158.8(5) . . . . ?
N1 C1 N2 C4 -171.4(8) . . . . ?
N1 C1 N2 C3 0.7(7) . . . . ?
C2 C3 N2 C4 173.2(6) . . . . ?
C2 C3 N2 C1 -0.7(7) . . . . ?
N6 C8 N5 C9 0.2(6) . . . . ?
N6 C8 N5 Ni1 177.2(4) . . . . ?
C10 C9 N5 C8 -0.1(7) . . . . ?
C10 C9 N5 Ni1 -177.1(4) . . . . ?
N7 C11 N6 C8 174.5(6) . . . . ?
C12 C11 N6 C8 -10.1(10) . . . . ?
N7 C11 N6 C10 -6.7(10) . . . . ?
C12 C11 N6 C10 168.6(5) . . . . ?
N5 C8 N6 C11 178.6(8) . . . . ?
N5 C8 N6 C10 -0.2(7) . . . . ?
C9 C10 N6 C11 -179.0(6) . . . . ?
C9 C10 N6 C8 0.1(7) . . . . ?
O2 C15 O1 Ni1 4.2(5) . . . . ?
C16 C15 O1 Ni1 -174.5(4) . . . . ?
O1 C15 O2 Ni1 -4.1(5) . . . . ?
C16 C15 O2 Ni1 174.6(4) . . . . ?
O5 C19 O4 Ni1 -18.0(10) . . . . ?
C20 C19 O4 Ni1 162.5(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
C1 H1 O1 0.93 2.61 3.089(6) 112.8 .
C1 H1 O6 0.93 2.45 3.36(2) 169.2 .
C3 H3 O2 0.93 2.56 3.358(7) 143.6 2
C5 H5 O2 0.93 2.53 3.045(8) 115.1 2
C8 H8 O3 0.93 2.35 3.222(7) 155.9 2_566
C12 H12 O6 0.93 2.56 3.05(2) 113.3 2_666
O3 H1W O5 0.83(2) 1.81(4) 2.565(6) 151(7) .
O3 H1W O6 0.83(2) 2.60(6) 3.19(2) 129(6) 1_455
O3 H2W O1 0.84(2) 1.94(3) 2.762(5) 166(6) 2_566
O6 H3W N7 1.16 1.89 2.74(3) 127.0 1_545
O6 H3W N8 1.16 1.45 2.54(3) 154.2 1_545
O6 H4W O5 0.84 1.91 2.73(2) 164.1 1_655

_refine_diff_density_max         1.065
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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 1527995'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N14 Ni S2'
_chemical_formula_weight         599.32

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.409(2)
_cell_length_b                   16.144(5)
_cell_length_c                   10.837(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.531(9)
_cell_angle_gamma                90
_cell_volume                     1236.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    978
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      20.78

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.999
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2137
_reflns_number_gt                1595
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0308P)²+0.9939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2137
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C -0.2771(5) 0.1508(2) 0.4512(3) 0.0287(9) Uani 1 1 d . . . . .
H1 H -0.1743 0.1356 0.5209 0.034 Uiso 1 1 calc R U . . .
C2 C -0.5524(6) 0.1559(2) 0.3127(4) 0.0380(10) Uani 1 1 d . . . . .
H2 H -0.6788 0.1442 0.2702 0.046 Uiso 1 1 calc R U . . .
C3 C -0.4489(5) 0.2154(2) 0.2767(4) 0.0367(10) Uani 1 1 d . . . . .
H3 H -0.4888 0.2504 0.2054 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1150(5) 0.2606(2) 0.3613(3) 0.0276(9) Uani 1 1 d . . . . .
C5 C 0.0290(6) 0.2820(3) 0.4714(4) 0.0507(13) Uani 1 1 d . . . . .
H5 H 0.0252 0.2669 0.5534 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1770(6) 0.3261(3) 0.4545(4) 0.0503(13) Uani 1 1 d . . . . .
H6 H 0.2775 0.3426 0.5250 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1729(5) 0.3455(2) 0.3295(3) 0.0272(9) Uani 1 1 d . . . . .
C8 C 0.4975(6) 0.4096(3) 0.3782(4) 0.0367(10) Uani 1 1 d . . . . .
H8 H 0.5448 0.4020 0.4672 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5867(6) 0.4453(2) 0.2996(4) 0.0359(10) Uani 1 1 d . . . . .
H9 H 0.7089 0.4666 0.3272 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3136(5) 0.4112(2) 0.1757(4) 0.0290(9) Uani 1 1 d . . . . .
H10 H 0.2088 0.4040 0.1033 0.035 Uiso 1 1 calc R U . . .
C11 C 0.0863(6) 0.4639(2) -0.1838(4) 0.0299(9) Uani 1 1 d . . . . .
N1 N -0.4418(4) 0.11526(18) 0.4220(3) 0.0274(7) Uani 1 1 d . . . . .
N2 N -0.2731(4) 0.21331(18) 0.3671(3) 0.0283(7) Uani 1 1 d . . . . .
N3 N -0.1187(5) 0.2837(2) 0.2440(3) 0.0347(8) Uani 1 1 d . . . . .
N4 N 0.0282(5) 0.3266(2) 0.2291(3) 0.0357(8) Uani 1 1 d . . . . .
N5 N 0.3208(4) 0.38704(18) 0.2980(3) 0.0286(7) Uani 1 1 d . . . . .
N6 N 0.4720(4) 0.44554(18) 0.1732(3) 0.0273(7) Uani 1 1 d . . . . .
N7 N 0.2122(5) 0.48293(19) -0.0948(3) 0.0311(8) Uani 1 1 d . . . . .
Ni1 Ni 0.5000 0.5000 0.0000 0.0227(2) Uani 1 2 d S . P . .
S1 S -0.08361(17) 0.43494(8) -0.31015(12) 0.0555(4) 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
C1 N1 1.298(4) . ?
C1 N2 1.366(4) . ?
C2 C3 1.357(5) . ?
C2 N1 1.387(5) . ?
C3 N2 1.375(5) . ?
C4 N3 1.317(5) . ?
C4 C5 1.384(5) . ?
C4 N2 1.415(5) . ?
C5 C6 1.365(6) . ?
C6 C7 1.382(5) . ?
C7 N4 1.313(5) . ?
C7 N5 1.411(5) . ?
C8 C9 1.354(5) . ?
C8 N5 1.385(5) . ?
C9 N6 1.377(5) . ?
C10 N6 1.306(5) . ?
C10 N5 1.366(4) . ?
C11 N7 1.163(5) . ?
C11 S1 1.625(4) . ?
N1 Ni1 2.140(3) 2_545 ?
N3 N4 1.341(4) . ?
N6 Ni1 2.139(3) . ?
N7 Ni1 2.088(3) . ?
Ni1 N7 2.088(3) 3_665 ?
Ni1 N6 2.139(3) 3_665 ?
Ni1 N1 2.140(3) 2 ?
Ni1 N1 2.140(3) 4_665 ?

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 C1 N2 111.9(3) . . ?
C3 C2 N1 109.9(3) . . ?
C2 C3 N2 105.9(3) . . ?
N3 C4 C5 123.2(4) . . ?
N3 C4 N2 114.7(3) . . ?
C5 C4 N2 122.0(3) . . ?
C6 C5 C4 117.2(4) . . ?
C5 C6 C7 117.9(4) . . ?
N4 C7 C6 122.1(4) . . ?
N4 C7 N5 114.2(3) . . ?
C6 C7 N5 123.7(3) . . ?
C9 C8 N5 105.4(3) . . ?
C8 C9 N6 110.8(4) . . ?
N6 C10 N5 111.6(3) . . ?
N7 C11 S1 177.6(4) . . ?
C1 N1 C2 105.6(3) . . ?
C1 N1 Ni1 125.1(2) . 2_545 ?
C2 N1 Ni1 127.7(2) . 2_545 ?
C1 N2 C3 106.7(3) . . ?
C1 N2 C4 127.8(3) . . ?
C3 N2 C4 125.1(3) . . ?
C4 N3 N4 118.7(3) . . ?
C7 N4 N3 120.7(3) . . ?
C10 N5 C8 106.7(3) . . ?
C10 N5 C7 124.3(3) . . ?
C8 N5 C7 129.0(3) . . ?
C10 N6 C9 105.5(3) . . ?
C10 N6 Ni1 121.2(2) . . ?
C9 N6 Ni1 132.9(3) . . ?
C11 N7 Ni1 152.7(3) . . ?
N7 Ni1 N7 180.0 . 3_665 ?
N7 Ni1 N6 91.31(12) . . ?
N7 Ni1 N6 88.69(12) 3_665 . ?
N7 Ni1 N6 88.69(12) . 3_665 ?
N7 Ni1 N6 91.31(12) 3_665 3_665 ?
N6 Ni1 N6 180.0 . 3_665 ?
N7 Ni1 N1 90.66(12) . 2 ?
N7 Ni1 N1 89.34(12) 3_665 2 ?
N6 Ni1 N1 85.79(11) . 2 ?
N6 Ni1 N1 94.21(11) 3_665 2 ?
N7 Ni1 N1 89.34(12) . 4_665 ?
N7 Ni1 N1 90.66(12) 3_665 4_665 ?
N6 Ni1 N1 94.21(11) . 4_665 ?
N6 Ni1 N1 85.79(11) 3_665 4_665 ?
N1 Ni1 N1 180.0 2 4_665 ?

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
N1 C2 C3 N2 -1.7(5) . . . . ?
N3 C4 C5 C6 -3.0(7) . . . . ?
N2 C4 C5 C6 178.6(4) . . . . ?
C4 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 N4 3.5(7) . . . . ?
C5 C6 C7 N5 -176.6(4) . . . . ?
N5 C8 C9 N6 -0.1(5) . . . . ?
N2 C1 N1 C2 0.3(4) . . . . ?
N2 C1 N1 Ni1 166.6(2) . . . 2_545 ?
C3 C2 N1 C1 0.9(5) . . . . ?
C3 C2 N1 Ni1 -165.0(3) . . . 2_545 ?
N1 C1 N2 C3 -1.4(4) . . . . ?
N1 C1 N2 C4 -173.9(3) . . . . ?
C2 C3 N2 C1 1.8(4) . . . . ?
C2 C3 N2 C4 174.6(4) . . . . ?
N3 C4 N2 C1 146.5(4) . . . . ?
C5 C4 N2 C1 -34.9(6) . . . . ?
N3 C4 N2 C3 -24.7(5) . . . . ?
C5 C4 N2 C3 153.9(4) . . . . ?
C5 C4 N3 N4 3.4(6) . . . . ?
N2 C4 N3 N4 -178.1(3) . . . . ?
C6 C7 N4 N3 -3.3(6) . . . . ?
N5 C7 N4 N3 176.9(3) . . . . ?
C4 N3 N4 C7 -0.2(6) . . . . ?
N6 C10 N5 C8 1.1(4) . . . . ?
N6 C10 N5 C7 -177.7(3) . . . . ?
C9 C8 N5 C10 -0.5(4) . . . . ?
C9 C8 N5 C7 178.1(4) . . . . ?
N4 C7 N5 C10 4.1(5) . . . . ?
C6 C7 N5 C10 -175.7(4) . . . . ?
N4 C7 N5 C8 -174.3(4) . . . . ?
C6 C7 N5 C8 5.8(6) . . . . ?
N5 C10 N6 C9 -1.1(4) . . . . ?
N5 C10 N6 Ni1 -174.5(2) . . . . ?
C8 C9 N6 C10 0.7(5) . . . . ?
C8 C9 N6 Ni1 173.1(3) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1528001'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Co N6 O5'
_chemical_formula_weight         527.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   16.979(3)
_cell_length_b                   24.792(5)
_cell_length_c                   6.1089(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2571.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1864
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.84

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16566
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.454
_diffrn_reflns_theta_max         25.143
_diffrn_reflns_theta_full        25.143
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4597
_reflns_number_gt                3470
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²+3.3335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     345
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2685
_refine_ls_wR_factor_gt          0.2576
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.525
_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
C1 C -0.1528(9) 0.7402(7) -0.438(2) 0.047(4) Uani 1 1 d . . . . .
H1 H -0.1924 0.7616 -0.3789 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0888(8) 0.6848(7) -0.647(3) 0.053(4) Uani 1 1 d . . . . .
H2 H -0.0777 0.6605 -0.7589 0.064 Uiso 1 1 calc R U . . .
C3 C -0.0386(9) 0.7005(7) -0.485(3) 0.057(4) Uani 1 1 d . . . . .
H3 H 0.0136 0.6899 -0.4688 0.069 Uiso 1 1 calc R U . . .
C4 C -0.0499(8) 0.7596(6) -0.161(3) 0.047(4) Uani 1 1 d . . . . .
N6 N 0.0175(7) 0.7369(5) -0.081(2) 0.055(4) Uani 1 1 d . . . . .
N5 N 0.0499(8) 0.7588(6) 0.089(2) 0.054(4) Uani 1 1 d . . . . .
C7 C 0.0204(7) 0.7992(7) 0.186(3) 0.051(4) Uani 1 1 d . . . . .
C6 C -0.0507(9) 0.8235(7) 0.124(3) 0.056(4) Uani 1 1 d . . . . .
H6 H -0.0721 0.8523 0.2018 0.068 Uiso 1 1 calc R U . . .
C5 C -0.0869(8) 0.8030(7) -0.057(2) 0.051(4) Uani 1 1 d . . . . .
H5 H -0.1340 0.8172 -0.1093 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1285(7) 0.7952(7) 0.449(2) 0.044(3) Uani 1 1 d . . . . .
H8 H 0.1553 0.7674 0.3792 0.053 Uiso 1 1 calc R U . . .
C9 C 0.0403(9) 0.8560(7) 0.526(3) 0.065(5) Uani 1 1 d . . . . .
H9 H -0.0045 0.8775 0.5206 0.078 Uiso 1 1 calc R U . . .
C10 C 0.0956(10) 0.8576(7) 0.681(3) 0.061(4) Uani 1 1 d . . . . .
H10 H 0.0964 0.8809 0.8006 0.073 Uiso 1 1 calc R U . . .
C18 C 0.2040(9) 0.6967(6) 0.893(2) 0.048(4) Uani 1 1 d . . . . .
C19 C 0.1722(12) 0.6457(6) 0.988(3) 0.061(3) Uani 1 1 d . U . . .
C20 C 0.1717(13) 0.6348(7) 1.198(3) 0.078(4) Uani 1 1 d . U . . .
H20 H 0.1906 0.6602 1.2965 0.094 Uiso 1 1 calc R U . . .
C21 C 0.1430(13) 0.5855(8) 1.275(3) 0.083(4) Uani 1 1 d . U . . .
H21 H 0.1416 0.5794 1.4249 0.099 Uiso 1 1 calc R U . . .
C22 C 0.1184(11) 0.5481(7) 1.143(3) 0.066(4) Uani 1 1 d . U . . .
C23A C 0.093(2) 0.5660(13) 0.960(6) 0.065(4) Uani 0.52(2) 1 d . U P A 1
H23A H 0.0528 0.5481 0.8877 0.078 Uiso 0.52(2) 1 calc R U P A 1
C24A C 0.126(2) 0.6124(12) 0.867(6) 0.064(4) Uani 0.52(2) 1 d . U P A 1
H24A H 0.1159 0.6205 0.7206 0.077 Uiso 0.52(2) 1 calc R U P A 1
C23B C 0.147(3) 0.5461(15) 0.907(6) 0.065(4) Uani 0.48(2) 1 d . U P A 2
H23B H 0.1395 0.5166 0.8156 0.078 Uiso 0.48(2) 1 calc R U P A 2
C24B C 0.186(3) 0.5947(14) 0.842(6) 0.065(4) Uani 0.48(2) 1 d . U P A 2
H24B H 0.2178 0.5958 0.7183 0.078 Uiso 0.48(2) 1 calc R U P A 2
Co1 Co 0.24525(11) 0.79461(7) 0.8172(3) 0.0365(5) Uani 1 1 d . . . . .
N1 N -0.1595(7) 0.7115(5) -0.6131(17) 0.039(3) Uani 1 1 d . . . . .
N2 N -0.0789(6) 0.7344(5) -0.3542(17) 0.040(3) Uani 1 1 d . . . . .
N3 N 0.0607(7) 0.8170(5) 0.375(2) 0.046(3) Uani 1 1 d . . . . .
N4 N 0.1522(7) 0.8182(5) 0.6340(18) 0.043(3) Uani 1 1 d . . . . .
O4 O 0.2289(5) 0.7328(4) 1.0260(16) 0.046(2) Uani 1 1 d . . . . .
O5 O 0.2063(8) 0.7035(5) 0.6927(18) 0.076(3) Uani 1 1 d . . . . .
O3 O 0.0890(7) 0.4995(5) 1.220(3) 0.093(5) Uani 1 1 d . . . . .
C15 C 0.1301(9) 0.4724(6) 1.386(3) 0.052(4) Uani 1 1 d . . . . .
C14 C 0.2079(10) 0.4654(7) 1.378(3) 0.058(4) Uani 1 1 d . . . . .
H14 H 0.2363 0.4803 1.2624 0.069 Uiso 1 1 calc R U . . .
C16 C 0.0878(11) 0.4476(8) 1.543(4) 0.094(8) Uani 1 1 d . . . . .
H16 H 0.0332 0.4504 1.5425 0.113 Uiso 1 1 calc R U . . .
C13 C 0.2472(11) 0.4361(7) 1.538(2) 0.060(4) Uani 1 1 d . . . . .
H13 H 0.3018 0.4330 1.5366 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1248(10) 0.4180(7) 1.707(3) 0.064(5) Uani 1 1 d . . . . .
H17 H 0.0954 0.4028 1.8197 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2025(9) 0.4115(5) 1.702(2) 0.045(3) Uani 1 1 d . . . . .
C11 C 0.2453(10) 0.3773(6) 1.871(2) 0.046(3) Uani 1 1 d . . . . .
O1 O 0.2036(7) 0.3472(4) 1.9911(18) 0.058(3) Uani 1 1 d . . . . .
O2 O 0.3170(9) 0.3827(7) 1.886(2) 0.091(5) 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
C1 N1 1.287(17) . ?
C1 N2 1.365(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(2) . ?
C2 N1 1.386(18) . ?
C2 H2 0.9300 . ?
C3 N2 1.347(18) . ?
C3 H3 0.9300 . ?
C4 N6 1.366(18) . ?
C4 C5 1.40(2) . ?
C4 N2 1.425(18) . ?
N6 N5 1.293(17) . ?
N5 C7 1.27(2) . ?
C7 N3 1.411(19) . ?
C7 C6 1.403(19) . ?
C6 C5 1.36(2) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C8 N4 1.327(17) . ?
C8 N3 1.351(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.34(2) . ?
C9 N3 1.38(2) . ?
C9 H9 0.9300 . ?
C10 N4 1.400(19) . ?
C10 H10 0.9300 . ?
C18 O5 1.239(18) . ?
C18 O4 1.279(17) . ?
C18 C19 1.49(2) . ?
C19 C24A 1.36(4) . ?
C19 C20 1.31(2) . ?
C19 C24B 1.57(4) . ?
C20 C21 1.40(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.30(3) . ?
C21 H21 0.9300 . ?
C22 C23A 1.28(4) . ?
C22 O3 1.386(19) . ?
C22 C23B 1.52(4) . ?
C23A C24A 1.40(4) . ?
C23A H23A 0.9300 . ?
C24A H24A 0.9300 . ?
C23B C24B 1.43(5) . ?
C23B H23B 0.9300 . ?
C24B H24B 0.9300 . ?
Co1 O1 1.957(11) 3_558 ?
Co1 O4 2.013(10) . ?
Co1 N1 2.048(11) 4_565 ?
Co1 N4 2.022(11) . ?
N1 Co1 2.048(11) 4_465 ?
O3 C15 1.405(18) . ?
C15 C14 1.33(2) . ?
C15 C16 1.35(2) . ?
C14 C13 1.39(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.39(2) . ?
C16 H16 0.9300 . ?
C13 C12 1.39(2) . ?
C13 H13 0.9300 . ?
C17 C12 1.33(2) . ?
C17 H17 0.9300 . ?
C12 C11 1.522(18) . ?
C11 O2 1.23(2) . ?
C11 O1 1.264(18) . ?
O1 Co1 1.957(11) 3_548 ?

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 C1 N2 109.6(13) . . ?
N1 C1 H1 125.2 . . ?
N2 C1 H1 125.2 . . ?
C3 C2 N1 107.3(13) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 106.9(13) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N6 C4 C5 122.2(14) . . ?
N6 C4 N2 113.8(13) . . ?
C5 C4 N2 124.0(12) . . ?
C4 N6 N5 118.0(13) . . ?
C7 N5 N6 122.8(13) . . ?
N5 C7 N3 116.1(12) . . ?
N5 C7 C6 123.5(15) . . ?
N3 C7 C6 120.3(15) . . ?
C5 C6 C7 116.6(15) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
C6 C5 C4 116.9(13) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
N4 C8 N3 111.9(13) . . ?
N4 C8 H8 124.1 . . ?
N3 C8 H8 124.1 . . ?
C10 C9 N3 108.7(13) . . ?
C10 C9 H9 125.7 . . ?
N3 C9 H9 125.7 . . ?
C9 C10 N4 108.4(14) . . ?
C9 C10 H10 125.8 . . ?
N4 C10 H10 125.8 . . ?
O5 C18 O4 121.3(15) . . ?
O5 C18 C19 120.7(15) . . ?
O4 C18 C19 117.9(13) . . ?
C24A C19 C20 114(2) . . ?
C20 C19 C24B 113.0(19) . . ?
C24A C19 C18 120.9(18) . . ?
C20 C19 C18 123.8(17) . . ?
C24B C19 C18 114.4(18) . . ?
C19 C20 C21 120.9(19) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 121.9(18) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23A C22 C21 114(2) . . ?
C23A C22 O3 119(2) . . ?
C21 C22 O3 121.9(17) . . ?
C21 C22 C23B 121(2) . . ?
O3 C22 C23B 114(2) . . ?
C22 C23A C24A 121(3) . . ?
C22 C23A H23A 119.7 . . ?
C24A C23A H23A 119.7 . . ?
C19 C24A C23A 121(3) . . ?
C19 C24A H24A 119.7 . . ?
C23A C24A H24A 119.7 . . ?
C24B C23B C22 113(3) . . ?
C24B C23B H23B 123.7 . . ?
C22 C23B H23B 123.7 . . ?
C23B C24B C19 117(3) . . ?
C23B C24B H24B 121.5 . . ?
C19 C24B H24B 121.5 . . ?
O1 Co1 O4 100.9(5) 3_558 . ?
O1 Co1 N1 93.6(5) 3_558 4_565 ?
O4 Co1 N1 116.0(4) . 4_565 ?
O1 Co1 N4 119.0(5) 3_558 . ?
O4 Co1 N4 117.6(4) . . ?
N1 Co1 N4 107.6(4) 4_565 . ?
C1 N1 C2 108.1(12) . . ?
C1 N1 Co1 127.9(10) . 4_465 ?
C2 N1 Co1 124.0(9) . 4_465 ?
C1 N2 C3 108.0(12) . . ?
C1 N2 C4 125.7(11) . . ?
C3 N2 C4 126.3(11) . . ?
C8 N3 C9 105.6(12) . . ?
C8 N3 C7 124.2(13) . . ?
C9 N3 C7 130.1(12) . . ?
C8 N4 C10 105.5(12) . . ?
C8 N4 Co1 125.7(10) . . ?
C10 N4 Co1 128.6(10) . . ?
C18 O4 Co1 100.2(8) . . ?
C22 O3 C15 118.9(13) . . ?
C14 C15 C16 119.9(15) . . ?
C14 C15 O3 121.7(15) . . ?
C16 C15 O3 117.9(15) . . ?
C15 C14 C13 121.0(16) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C17 C16 C15 120.8(17) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C14 C13 C12 118.2(17) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C12 C17 C16 119.6(17) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C12 C13 120.3(15) . . ?
C17 C12 C11 121.7(15) . . ?
C13 C12 C11 118.0(14) . . ?
O2 C11 O1 125.3(13) . . ?
O2 C11 C12 117.6(14) . . ?
O1 C11 C12 117.1(14) . . ?
C11 O1 Co1 119.5(10) . 3_548 ?

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
N1 C2 C3 N2 2.0(19) . . . . ?
C5 C4 N6 N5 -4(2) . . . . ?
N2 C4 N6 N5 176.9(14) . . . . ?
C4 N6 N5 C7 2(2) . . . . ?
N6 N5 C7 N3 177.2(14) . . . . ?
N6 N5 C7 C6 1(3) . . . . ?
N5 C7 C6 C5 -3(3) . . . . ?
N3 C7 C6 C5 -178.4(14) . . . . ?
C7 C6 C5 C4 0(2) . . . . ?
N6 C4 C5 C6 3(2) . . . . ?
N2 C4 C5 C6 -178.5(14) . . . . ?
N3 C9 C10 N4 -1(2) . . . . ?
O5 C18 C19 C24A -18(3) . . . . ?
O4 C18 C19 C24A 162(2) . . . . ?
O5 C18 C19 C20 177(2) . . . . ?
O4 C18 C19 C20 -3(3) . . . . ?
O5 C18 C19 C24B 31(3) . . . . ?
O4 C18 C19 C24B -148(2) . . . . ?
C24A C19 C20 C21 16(4) . . . . ?
C24B C19 C20 C21 -33(3) . . . . ?
C18 C19 C20 C21 -178.2(18) . . . . ?
C19 C20 C21 C22 2(4) . . . . ?
C20 C21 C22 C23A -26(4) . . . . ?
C20 C21 C22 O3 -179.1(19) . . . . ?
C20 C21 C22 C23B 23(4) . . . . ?
C21 C22 C23A C24A 32(5) . . . . ?
O3 C22 C23A C24A -175(3) . . . . ?
C20 C19 C24A C23A -10(5) . . . . ?
C18 C19 C24A C23A -177(3) . . . . ?
C22 C23A C24A C19 -14(6) . . . . ?
C21 C22 C23B C24B -13(4) . . . . ?
O3 C22 C23B C24B -173(3) . . . . ?
C22 C23B C24B C19 -17(5) . . . . ?
C20 C19 C24B C23B 40(4) . . . . ?
C18 C19 C24B C23B -171(3) . . . . ?
N2 C1 N1 C2 1.0(17) . . . . ?
N2 C1 N1 Co1 -177.9(9) . . . 4_465 ?
C3 C2 N1 C1 -1.9(18) . . . . ?
C3 C2 N1 Co1 177.1(11) . . . 4_465 ?
N1 C1 N2 C3 0.2(18) . . . . ?
N1 C1 N2 C4 -179.6(13) . . . . ?
C2 C3 N2 C1 -1.4(19) . . . . ?
C2 C3 N2 C4 178.4(14) . . . . ?
N6 C4 N2 C1 163.8(14) . . . . ?
C5 C4 N2 C1 -15(2) . . . . ?
N6 C4 N2 C3 -16(2) . . . . ?
C5 C4 N2 C3 165.4(16) . . . . ?
N4 C8 N3 C9 -0.7(18) . . . . ?
N4 C8 N3 C7 -177.6(13) . . . . ?
C10 C9 N3 C8 1(2) . . . . ?
C10 C9 N3 C7 177.9(15) . . . . ?
N5 C7 N3 C8 3(2) . . . . ?
C6 C7 N3 C8 178.7(15) . . . . ?
N5 C7 N3 C9 -173.4(17) . . . . ?
C6 C7 N3 C9 3(3) . . . . ?
N3 C8 N4 C10 -0.1(17) . . . . ?
N3 C8 N4 Co1 174.6(10) . . . . ?
C9 C10 N4 C8 0.9(19) . . . . ?
C9 C10 N4 Co1 -173.6(12) . . . . ?
O5 C18 O4 Co1 9.7(17) . . . . ?
C19 C18 O4 Co1 -170.5(12) . . . . ?
C23A C22 O3 C15 163(3) . . . . ?
C21 C22 O3 C15 -46(3) . . . . ?
C23B C22 O3 C15 113(3) . . . . ?
C22 O3 C15 C14 -47(3) . . . . ?
C22 O3 C15 C16 141(2) . . . . ?
C16 C15 C14 C13 -5(3) . . . . ?
O3 C15 C14 C13 -176.8(16) . . . . ?
C14 C15 C16 C17 5(3) . . . . ?
O3 C15 C16 C17 177.0(19) . . . . ?
C15 C14 C13 C12 4(3) . . . . ?
C15 C16 C17 C12 -4(3) . . . . ?
C16 C17 C12 C13 3(3) . . . . ?
C16 C17 C12 C11 -177.2(18) . . . . ?
C14 C13 C12 C17 -3(2) . . . . ?
C14 C13 C12 C11 177.2(14) . . . . ?
C17 C12 C11 O2 -164.1(17) . . . . ?
C13 C12 C11 O2 16(2) . . . . ?
C17 C12 C11 O1 13(2) . . . . ?
C13 C12 C11 O1 -166.8(13) . . . . ?
O2 C11 O1 Co1 -12(2) . . . 3_548 ?
C12 C11 O1 Co1 171.2(9) . . . 3_548 ?

_refine_diff_density_max         1.293
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.133



####################################################################### 
# 
# 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 1527996'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H26 Cu5 N6 O18'
_chemical_formula_weight         1220.39

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.6597(11)
_cell_length_b                   11.1980(16)
_cell_length_c                   13.3076(18)
_cell_angle_alpha                110.824(4)
_cell_angle_beta                 95.302(4)
_cell_angle_gamma                104.344(4)
_cell_volume                     1012.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1390
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      24.45

_exptl_crystal_description       Block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_F_000             609
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.676
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6636
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.671
_diffrn_reflns_theta_max         25.179
_diffrn_reflns_theta_full        25.179
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3611
_reflns_number_gt                2837
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     343
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.022
_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
C23 C 0.0651(14) 0.0752(10) -0.0746(9) 0.020(2) Uani 0.5 1 d . U P A 1
H23 H 0.1165 0.1137 -0.1207 0.024 Uiso 0.5 1 calc R U P A 1
C22 C -0.0732(16) 0.1098(11) -0.0253(9) 0.025(3) Uani 0.5 1 d . U P A 1
H22 H -0.1266 0.1721 -0.0348 0.030 Uiso 0.5 1 calc R U P A 1
N3 N 0.0925(14) 0.0556(10) -0.0481(8) 0.029(2) Uani 0.5 1 d . U P A 2
N4 N -0.0454(13) 0.0913(9) 0.0003(8) 0.026(2) Uani 0.5 1 d . U P A 2
C1 C -0.3614(6) 0.0178(4) 0.1644(3) 0.0209(10) Uani 1 1 d . . . . .
H1 H -0.3371 -0.0508 0.1816 0.025 Uiso 1 1 calc R U . . .
C2 C -0.4787(7) 0.1711(5) 0.1549(4) 0.0311(12) Uani 1 1 d . . . . .
H2 H -0.5522 0.2276 0.1660 0.037 Uiso 1 1 calc R U . . .
C3 C -0.3498(8) 0.1691(5) 0.0926(4) 0.0352(13) Uani 1 1 d . . . . .
H3 H -0.3179 0.2222 0.0530 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1306(7) 0.0327(6) 0.0485(4) 0.0380(14) Uani 1 1 d . . . . .
C6 C -0.1856(6) 0.1973(4) 0.4754(3) 0.0177(9) Uani 1 1 d . . . . .
C7 C -0.1321(6) 0.2827(4) 0.4118(3) 0.0171(9) Uani 1 1 d . . . . .
C8 C -0.2163(6) 0.3816(4) 0.4211(3) 0.0205(10) Uani 1 1 d . . . . .
H8 H -0.3110 0.3863 0.4600 0.025 Uiso 1 1 calc R U . . .
C9 C -0.1631(6) 0.4727(4) 0.3741(4) 0.0245(11) Uani 1 1 d . . . . .
H9 H -0.2194 0.5393 0.3825 0.029 Uiso 1 1 calc R U . . .
C10 C -0.0248(7) 0.4640(4) 0.3144(4) 0.0266(11) Uani 1 1 d . . . . .
H10 H 0.0127 0.5255 0.2827 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0584(6) 0.3634(4) 0.3015(3) 0.0223(10) Uani 1 1 d . . . . .
H11 H 0.1503 0.3575 0.2605 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0051(6) 0.2717(4) 0.3495(3) 0.0180(10) Uani 1 1 d . . . . .
C13 C 0.0868(6) 0.1582(4) 0.3290(3) 0.0190(10) Uani 1 1 d . . . . .
C14 C 0.3338(6) 0.2698(4) 0.6945(4) 0.0202(10) Uani 1 1 d . . . . .
C15 C 0.4846(6) 0.3712(4) 0.7883(3) 0.0169(9) Uani 1 1 d . . . . .
C16 C 0.4592(7) 0.4944(4) 0.8477(4) 0.0268(11) Uani 1 1 d . . . . .
H16 H 0.3491 0.5103 0.8302 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5954(8) 0.5921(5) 0.9315(4) 0.0334(12) Uani 1 1 d . . . . .
H17 H 0.5765 0.6736 0.9705 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7600(8) 0.5711(5) 0.9586(4) 0.0368(13) Uani 1 1 d . . . . .
H18 H 0.8518 0.6376 1.0156 0.044 Uiso 1 1 calc R U . . .
C19 C 0.7864(7) 0.4503(5) 0.9001(4) 0.0301(12) Uani 1 1 d . . . . .
H19 H 0.8983 0.4364 0.9172 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6510(6) 0.3495(4) 0.8169(3) 0.0183(10) Uani 1 1 d . . . . .
Cu1 Cu -0.61840(7) 0.05107(5) 0.31162(4) 0.01818(15) Uani 1 1 d . . . . .
Cu2 Cu -0.5000 0.0000 0.5000 0.01890(19) Uani 1 2 d S . P . .
Cu3 Cu -0.04210(7) 0.09409(5) 0.63394(4) 0.01601(15) Uani 1 1 d . . . . .
N1 N -0.4856(5) 0.0768(4) 0.2000(3) 0.0204(9) Uani 1 1 d . . . . .
N2 N -0.2749(5) 0.0711(4) 0.0999(3) 0.0258(9) Uani 1 1 d . . . . .
O1 O -0.0146(4) 0.0517(3) 0.3294(2) 0.0237(7) Uani 1 1 d . . . . .
O2 O 0.2481(4) 0.1779(3) 0.3107(3) 0.0266(8) Uani 1 1 d . . . . .
O3 O -0.3548(4) 0.1378(3) 0.4582(2) 0.0213(7) Uani 1 1 d . . . . .
O4 O -0.0616(4) 0.1994(3) 0.5446(3) 0.0265(7) Uani 1 1 d . . . . .
O5 O 0.3524(4) 0.2562(3) 0.6004(2) 0.0268(8) Uani 1 1 d . . . . .
O6 O 0.1926(4) 0.2107(3) 0.7221(2) 0.0247(7) Uani 1 1 d . . . . .
O9 O -0.2853(4) -0.0309(3) 0.5627(2) 0.0150(6) Uani 1 1 d D . . . .
H1O H -0.293(6) -0.104(3) 0.517(3) 0.018 Uiso 1 1 d D U . . .
C21 C 0.6848(6) 0.2161(4) 0.7628(3) 0.0200(10) Uani 1 1 d . . . . .
O7 O 0.8432(4) 0.2090(3) 0.7780(3) 0.0383(9) Uani 1 1 d . . . . .
O8 O 0.5465(4) 0.1147(3) 0.7089(2) 0.0226(7) 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
C23 C22 1.361(14) . ?
C23 C4 1.549(12) 2 ?
C23 H23 0.9300 . ?
C22 C4 1.548(12) . ?
C22 H22 0.9300 . ?
N3 C4 1.096(10) 2 ?
N3 N4 1.357(12) . ?
N4 C4 1.196(10) . ?
C1 N1 1.318(5) . ?
C1 N2 1.344(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(6) . ?
C2 N1 1.381(5) . ?
C2 H2 0.9300 . ?
C3 N2 1.386(6) . ?
C3 H3 0.9300 . ?
C4 N3 1.097(10) 2 ?
C4 N2 1.429(5) . ?
C4 C23 1.549(12) 2 ?
C6 O4 1.250(5) . ?
C6 O3 1.259(5) . ?
C6 C7 1.498(6) . ?
C7 C8 1.390(5) . ?
C7 C12 1.400(5) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.503(5) . ?
C13 O1 1.254(5) . ?
C13 O2 1.262(5) . ?
C14 O5 1.234(5) . ?
C14 O6 1.278(5) . ?
C14 C15 1.502(6) . ?
C15 C16 1.397(6) . ?
C15 C20 1.400(6) . ?
C16 C17 1.372(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.509(5) . ?
Cu1 N1 1.940(3) . ?
Cu1 O2 1.948(3) 1_455 ?
Cu1 O9 1.951(3) 2_456 ?
Cu1 O8 1.999(3) 2_556 ?
Cu1 O3 2.404(3) . ?
Cu1 Cu2 2.8793(6) . ?
Cu1 Cu3 3.0034(8) 2_456 ?
Cu2 O9 1.938(3) 2_456 ?
Cu2 O9 1.938(3) . ?
Cu2 O3 1.949(3) . ?
Cu2 O3 1.949(3) 2_456 ?
Cu2 Cu1 2.8793(6) 2_456 ?
Cu3 O6 1.916(3) . ?
Cu3 O9 1.941(3) . ?
Cu3 O4 1.969(3) . ?
Cu3 O1 1.992(3) 2_556 ?
Cu3 O7 2.285(3) 1_455 ?
Cu3 Cu1 3.0034(8) 2_456 ?
O1 Cu3 1.992(3) 2_556 ?
O2 Cu1 1.948(3) 1_655 ?
O9 Cu1 1.951(3) 2_456 ?
O9 H1O 0.816(19) . ?
C21 O7 1.239(5) . ?
C21 O8 1.268(5) . ?
O7 Cu3 2.285(3) 1_655 ?
O8 Cu1 2.000(3) 2_556 ?

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
C22 C23 C4 115.2(9) . 2 ?
C22 C23 H23 122.4 . . ?
C4 C23 H23 122.4 2 . ?
C23 C22 C4 111.7(10) . . ?
C23 C22 H22 124.2 . . ?
C4 C22 H22 124.2 . . ?
C4 N3 N4 121.8(9) 2 . ?
C4 N4 N3 123.4(9) . . ?
N1 C1 N2 110.3(4) . . ?
N1 C1 H1 124.9 . . ?
N2 C1 H1 124.9 . . ?
C3 C2 N1 109.9(4) . . ?
C3 C2 H2 125.0 . . ?
N1 C2 H2 125.0 . . ?
C2 C3 N2 105.3(4) . . ?
C2 C3 H3 127.3 . . ?
N2 C3 H3 127.3 . . ?
N3 C4 N4 114.8(7) 2 . ?
N3 C4 N2 122.0(7) 2 . ?
N4 C4 N2 123.2(6) . . ?
N2 C4 C22 110.8(6) . . ?
N2 C4 C23 116.1(5) . 2 ?
C22 C4 C23 133.1(6) . 2 ?
O4 C6 O3 126.8(4) . . ?
O4 C6 C7 117.4(4) . . ?
O3 C6 C7 115.6(4) . . ?
C8 C7 C12 119.4(4) . . ?
C8 C7 C6 117.7(3) . . ?
C12 C7 C6 122.9(3) . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.2(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.0(4) . . ?
C11 C12 C13 120.0(4) . . ?
C7 C12 C13 120.8(4) . . ?
O1 C13 O2 126.3(4) . . ?
O1 C13 C12 116.3(4) . . ?
O2 C13 C12 117.3(4) . . ?
O5 C14 O6 126.5(4) . . ?
O5 C14 C15 118.2(4) . . ?
O6 C14 C15 115.2(4) . . ?
C16 C15 C20 118.5(4) . . ?
C16 C15 C14 118.3(4) . . ?
C20 C15 C14 123.1(4) . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.0(5) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.5(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 119.6(4) . . ?
C19 C20 C21 118.3(4) . . ?
C15 C20 C21 122.1(4) . . ?
N1 Cu1 O2 94.34(13) . 1_455 ?
N1 Cu1 O9 171.14(14) . 2_456 ?
O2 Cu1 O9 91.10(11) 1_455 2_456 ?
N1 Cu1 O8 89.85(13) . 2_556 ?
O2 Cu1 O8 164.69(14) 1_455 2_556 ?
O9 Cu1 O8 86.70(11) 2_456 2_556 ?
N1 Cu1 O3 96.73(13) . . ?
O2 Cu1 O3 114.86(12) 1_455 . ?
O9 Cu1 O3 74.61(11) 2_456 . ?
O8 Cu1 O3 79.15(12) 2_556 . ?
N1 Cu1 Cu2 129.54(11) . . ?
O2 Cu1 Cu2 125.62(9) 1_455 . ?
O9 Cu1 Cu2 42.06(8) 2_456 . ?
O8 Cu1 Cu2 60.16(9) 2_556 . ?
O3 Cu1 Cu2 42.12(7) . . ?
N1 Cu1 Cu3 148.21(12) . 2_456 ?
O2 Cu1 Cu3 84.74(9) 1_455 2_456 ?
O9 Cu1 Cu3 39.36(9) 2_456 2_456 ?
O8 Cu1 Cu3 83.96(9) 2_556 2_456 ?
O3 Cu1 Cu3 112.52(7) . 2_456 ?
Cu2 Cu1 Cu3 73.045(17) . 2_456 ?
O9 Cu2 O9 180.00(16) 2_456 . ?
O9 Cu2 O3 86.50(12) 2_456 . ?
O9 Cu2 O3 93.49(12) . . ?
O9 Cu2 O3 93.49(12) 2_456 2_456 ?
O9 Cu2 O3 86.51(12) . 2_456 ?
O3 Cu2 O3 180.0 . 2_456 ?
O9 Cu2 Cu1 42.40(8) 2_456 . ?
O9 Cu2 Cu1 137.60(8) . . ?
O3 Cu2 Cu1 55.79(9) . . ?
O3 Cu2 Cu1 124.21(9) 2_456 . ?
O9 Cu2 Cu1 137.60(8) 2_456 2_456 ?
O9 Cu2 Cu1 42.40(8) . 2_456 ?
O3 Cu2 Cu1 124.21(9) . 2_456 ?
O3 Cu2 Cu1 55.79(9) 2_456 2_456 ?
Cu1 Cu2 Cu1 180.0 . 2_456 ?
O6 Cu3 O9 171.67(12) . . ?
O6 Cu3 O4 94.99(13) . . ?
O9 Cu3 O4 92.47(12) . . ?
O6 Cu3 O1 87.97(13) . 2_556 ?
O9 Cu3 O1 86.64(12) . 2_556 ?
O4 Cu3 O1 156.47(12) . 2_556 ?
O6 Cu3 O7 84.61(12) . 1_455 ?
O9 Cu3 O7 90.67(12) . 1_455 ?
O4 Cu3 O7 98.41(13) . 1_455 ?
O1 Cu3 O7 105.11(13) 2_556 1_455 ?
O6 Cu3 Cu1 132.37(9) . 2_456 ?
O9 Cu3 Cu1 39.60(8) . 2_456 ?
O4 Cu3 Cu1 119.99(9) . 2_456 ?
O1 Cu3 Cu1 72.57(9) 2_556 2_456 ?
O7 Cu3 Cu1 60.74(10) 1_455 2_456 ?
C1 N1 C2 106.3(3) . . ?
C1 N1 Cu1 124.7(3) . . ?
C2 N1 Cu1 128.3(3) . . ?
C1 N2 C3 108.1(3) . . ?
C1 N2 C4 125.5(4) . . ?
C3 N2 C4 126.4(4) . . ?
C13 O1 Cu3 132.0(3) . 2_556 ?
C13 O2 Cu1 119.8(3) . 1_655 ?
C6 O3 Cu2 134.3(3) . . ?
C6 O3 Cu1 138.0(3) . . ?
Cu2 O3 Cu1 82.10(11) . . ?
C6 O4 Cu3 135.1(3) . . ?
C14 O6 Cu3 129.9(3) . . ?
Cu2 O9 Cu3 129.12(15) . . ?
Cu2 O9 Cu1 95.54(11) . 2_456 ?
Cu3 O9 Cu1 101.04(13) . 2_456 ?
Cu2 O9 H1O 100(3) . . ?
Cu3 O9 H1O 118(3) . . ?
Cu1 O9 H1O 110(3) 2_456 . ?
O7 C21 O8 123.1(4) . . ?
O7 C21 C20 118.9(4) . . ?
O8 C21 C20 117.8(4) . . ?
C21 O7 Cu3 120.1(3) . 1_655 ?
C21 O8 Cu1 108.7(3) . 2_556 ?

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
C4 C23 C22 C4 1.0(13) 2 . . . ?
C4 N3 N4 C4 2.4(18) 2 . . . ?
N1 C2 C3 N2 -0.2(6) . . . . ?
N3 N4 C4 N3 -2.2(16) . . . 2 ?
N3 N4 C4 N2 179.6(8) . . . . ?
C23 C22 C4 N2 179.6(8) . . . . ?
C23 C22 C4 C23 -1.3(16) . . . 2 ?
O4 C6 C7 C8 -119.8(4) . . . . ?
O3 C6 C7 C8 55.5(6) . . . . ?
O4 C6 C7 C12 56.4(6) . . . . ?
O3 C6 C7 C12 -128.2(4) . . . . ?
C12 C7 C8 C9 -2.7(7) . . . . ?
C6 C7 C8 C9 173.7(4) . . . . ?
C7 C8 C9 C10 1.3(7) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C10 C11 C12 C13 175.9(4) . . . . ?
C8 C7 C12 C11 2.3(7) . . . . ?
C6 C7 C12 C11 -173.9(4) . . . . ?
C8 C7 C12 C13 -174.3(4) . . . . ?
C6 C7 C12 C13 9.6(7) . . . . ?
C11 C12 C13 O1 -148.9(4) . . . . ?
C7 C12 C13 O1 27.6(6) . . . . ?
C11 C12 C13 O2 29.6(6) . . . . ?
C7 C12 C13 O2 -153.9(4) . . . . ?
O5 C14 C15 C16 101.7(4) . . . . ?
O6 C14 C15 C16 -74.6(5) . . . . ?
O5 C14 C15 C20 -76.4(5) . . . . ?
O6 C14 C15 C20 107.2(4) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
C14 C15 C16 C17 -177.7(4) . . . . ?
C15 C16 C17 C18 0.2(7) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C17 C18 C19 C20 -1.3(8) . . . . ?
C18 C19 C20 C15 2.1(7) . . . . ?
C18 C19 C20 C21 -175.1(4) . . . . ?
C16 C15 C20 C19 -1.7(6) . . . . ?
C14 C15 C20 C19 176.5(4) . . . . ?
C16 C15 C20 C21 175.4(4) . . . . ?
C14 C15 C20 C21 -6.4(6) . . . . ?
N2 C1 N1 C2 0.6(5) . . . . ?
N2 C1 N1 Cu1 -170.7(3) . . . . ?
C3 C2 N1 C1 -0.2(6) . . . . ?
C3 C2 N1 Cu1 170.6(4) . . . . ?
N1 C1 N2 C3 -0.8(5) . . . . ?
N1 C1 N2 C4 179.1(4) . . . . ?
C2 C3 N2 C1 0.6(6) . . . . ?
C2 C3 N2 C4 -179.3(5) . . . . ?
N3 C4 N2 C1 9.4(10) 2 . . . ?
N4 C4 N2 C1 -172.6(7) . . . . ?
C22 C4 N2 C1 176.5(6) . . . . ?
C23 C4 N2 C1 -2.8(8) 2 . . . ?
N3 C4 N2 C3 -170.8(8) 2 . . . ?
N4 C4 N2 C3 7.3(10) . . . . ?
C22 C4 N2 C3 -3.7(8) . . . . ?
C23 C4 N2 C3 177.1(6) 2 . . . ?
O2 C13 O1 Cu3 29.8(7) . . . 2_556 ?
C12 C13 O1 Cu3 -151.8(3) . . . 2_556 ?
O1 C13 O2 Cu1 -13.6(6) . . . 1_655 ?
C12 C13 O2 Cu1 168.1(3) . . . 1_655 ?
O4 C6 O3 Cu2 -14.3(7) . . . . ?
C7 C6 O3 Cu2 170.8(3) . . . . ?
O4 C6 O3 Cu1 -156.9(3) . . . . ?
C7 C6 O3 Cu1 28.2(6) . . . . ?
O3 C6 O4 Cu3 15.4(7) . . . . ?
C7 C6 O4 Cu3 -169.8(3) . . . . ?
O5 C14 O6 Cu3 -5.3(6) . . . . ?
C15 C14 O6 Cu3 170.7(2) . . . . ?
C19 C20 C21 O7 -14.6(6) . . . . ?
C15 C20 C21 O7 168.2(4) . . . . ?
C19 C20 C21 O8 161.2(4) . . . . ?
C15 C20 C21 O8 -16.0(6) . . . . ?
O8 C21 O7 Cu3 49.1(6) . . . 1_655 ?
C20 C21 O7 Cu3 -135.3(3) . . . 1_655 ?
O7 C21 O8 Cu1 13.5(5) . . . 2_556 ?
C20 C21 O8 Cu1 -162.1(3) . . . 2_556 ?

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
C23 H23 O1 0.93 2.64 3.119(11) 112.5 2
C1 H1 O8 0.93 2.41 2.869(5) 110.3 2_556
O9 H1O O5 0.816(19) 1.77(2) 2.569(4) 166(5) 2_556

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1528000'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cu2 N8 O10'
_chemical_formula_weight         705.54

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.8758(3)
_cell_length_b                   10.5245(5)
_cell_length_c                   21.6313(9)
_cell_angle_alpha                80.5010(10)
_cell_angle_beta                 84.0300(10)
_cell_angle_gamma                72.1610(10)
_cell_volume                     1467.26(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.08

_exptl_crystal_description       Block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.517
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9723
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.956
_diffrn_reflns_theta_max         25.156
_diffrn_reflns_theta_full        25.156
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5243
_reflns_number_gt                4356
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5243
_refine_ls_number_parameters     409
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.616
_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
C1 C 0.3851(4) 0.0203(3) 0.77629(14) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.3306(4) -0.0010(3) 0.84631(14) 0.0230(6) Uani 1 1 d . . . . .
C3 C 0.2938(5) -0.1134(3) 0.88200(16) 0.0301(7) Uani 1 1 d . . . . .
H3 H 0.2977 -0.1882 0.8637 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2505(5) -0.1117(3) 0.94666(16) 0.0345(8) Uani 1 1 d . . . . .
H4 H 0.2229 -0.1856 0.9717 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2484(5) -0.0006(3) 0.97341(16) 0.0326(7) Uani 1 1 d . . . . .
H5 H 0.2231 0.0005 1.0164 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2849(5) 0.1079(3) 0.93472(14) 0.0248(6) Uani 1 1 d . . . . .
C7 C 0.2874(5) 0.2412(3) 0.95303(14) 0.0292(7) Uani 1 1 d . . . . .
C8 C 0.5145(5) 0.4234(3) 0.71346(14) 0.0268(7) Uani 1 1 d . . . . .
H8 H 0.5421 0.3571 0.6875 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4329(5) 0.5297(3) 0.79384(15) 0.0284(7) Uani 1 1 d . . . . .
H9 H 0.3924 0.5482 0.8346 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4783(5) 0.6160(3) 0.74680(15) 0.0282(7) Uani 1 1 d . . . . .
H10 H 0.4755 0.7043 0.7485 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5842(4) 0.6017(3) 0.63312(13) 0.0222(6) Uani 1 1 d . . . . .
C12 C 0.5710(5) 0.7387(3) 0.61747(15) 0.0268(7) Uani 1 1 d . . . . .
H12 H 0.5277 0.7984 0.6468 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6254(5) 0.7790(3) 0.55687(15) 0.0282(7) Uani 1 1 d . . . . .
H13 H 0.6180 0.8686 0.5427 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6924(4) 0.6819(3) 0.51679(14) 0.0244(6) Uani 1 1 d . . . . .
C15 C 0.8072(4) 0.8271(3) 0.42809(14) 0.0262(7) Uani 1 1 d . . . . .
H15 H 0.7913 0.9004 0.4490 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8057(5) 0.6289(3) 0.40793(15) 0.0340(8) Uani 1 1 d . . . . .
H16 H 0.7881 0.5437 0.4119 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8816(5) 0.6944(3) 0.35685(15) 0.0339(8) Uani 1 1 d . . . . .
H17 H 0.9277 0.6607 0.3191 0.041 Uiso 1 1 calc R U . . .
C18 C 0.9482(5) 1.2094(3) 0.34405(15) 0.0293(7) Uani 1 1 d . . . . .
C19 C 1.0312(5) 1.2080(3) 0.27615(15) 0.0257(7) Uani 1 1 d . . . . .
C20 C 1.0742(5) 1.3131(3) 0.23583(17) 0.0333(8) Uani 1 1 d . . . . .
H20 H 1.0546 1.3961 0.2490 0.040 Uiso 1 1 calc R U . . .
C21 C 1.1469(5) 1.2919(3) 0.17560(17) 0.0358(8) Uani 1 1 d . . . . .
H21 H 1.1782 1.3610 0.1477 0.043 Uiso 1 1 calc R U . . .
C22 C 1.1746(5) 1.1660(3) 0.15578(15) 0.0311(7) Uani 1 1 d . . . . .
H22 H 1.2220 1.1508 0.1150 0.037 Uiso 1 1 calc R U . . .
C23 C 1.1285(4) 1.0667(3) 0.19934(14) 0.0232(6) Uani 1 1 d . . . . .
C24 C 1.1457(4) 0.9235(3) 0.18909(14) 0.0259(6) Uani 1 1 d . . . . .
Cu1 Cu 0.37451(6) 0.25887(3) 0.82231(2) 0.02463(15) Uani 1 1 d . . . . .
Cu2 Cu 0.99165(6) 0.94983(4) 0.31491(2) 0.02446(14) Uani 1 1 d . . . . .
N1 N 0.3232(4) 0.1053(2) 0.87330(12) 0.0224(5) Uani 1 1 d . . . . .
N2 N 0.4547(4) 0.4082(3) 0.77345(12) 0.0251(6) Uani 1 1 d . . . . .
N3 N 0.5301(4) 0.5494(2) 0.69508(12) 0.0229(5) Uani 1 1 d . . . . .
N4 N 0.6415(4) 0.5142(3) 0.59372(12) 0.0333(6) Uani 1 1 d . . . . .
N5 N 0.6993(5) 0.5545(3) 0.53381(12) 0.0323(6) Uani 1 1 d . . . . .
N6 N 0.7591(4) 0.7139(2) 0.45337(11) 0.0246(5) Uani 1 1 d . . . . .
N7 N 0.8803(4) 0.8192(3) 0.36919(12) 0.0268(6) Uani 1 1 d . . . . .
N8 N 1.0601(4) 1.0898(3) 0.25740(12) 0.0222(5) Uani 1 1 d . . . . .
O1 O 0.2477(4) 0.2614(3) 1.00755(11) 0.0448(6) Uani 1 1 d . . . . .
O2 O 0.3332(4) 0.3231(2) 0.90746(10) 0.0348(6) Uani 1 1 d . . . . .
O3 O 0.3898(4) -0.0658(2) 0.74360(11) 0.0357(6) Uani 1 1 d . . . . .
O4 O 0.4234(3) 0.1327(2) 0.75664(10) 0.0266(5) Uani 1 1 d . . . . .
O5 O 0.0298(4) 0.3563(2) 0.80113(12) 0.0377(6) Uani 1 1 d D . . . .
H1W H -0.016(6) 0.298(3) 0.791(2) 0.056 Uiso 1 1 d D U . . .
H2W H -0.030(6) 0.367(4) 0.8359(12) 0.056 Uiso 1 1 d D U . . .
O6 O 1.3203(4) 0.8574(3) 0.34841(11) 0.0358(6) Uani 1 1 d D . . . .
H3W H 1.403(5) 0.879(4) 0.3207(15) 0.054 Uiso 1 1 d D U . . .
H4W H 1.344(6) 0.883(4) 0.3809(14) 0.054 Uiso 1 1 d D U . . .
O7 O 1.0753(3) 0.8557(2) 0.23670(10) 0.0283(5) Uani 1 1 d . . . . .
O8 O 1.2229(4) 0.8840(3) 0.13984(11) 0.0387(6) Uani 1 1 d . . . . .
O9 O 0.9205(4) 1.0981(2) 0.37142(11) 0.0337(5) Uani 1 1 d . . . . .
O10 O 0.9147(4) 1.3129(2) 0.36758(12) 0.0445(6) 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
C1 O3 1.229(4) . ?
C1 O4 1.285(4) . ?
C1 C2 1.519(4) . ?
C2 N1 1.330(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.402(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.331(4) . ?
C6 C7 1.525(4) . ?
C7 O1 1.221(4) . ?
C7 O2 1.279(4) . ?
C8 N2 1.319(4) . ?
C8 N3 1.354(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.327(5) . ?
C9 N2 1.380(4) . ?
C9 H9 0.9300 . ?
C10 N3 1.376(4) . ?
C10 H10 0.9300 . ?
C11 N4 1.302(4) . ?
C11 N3 1.420(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.360(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9300 . ?
C14 N5 1.318(4) . ?
C14 N6 1.420(4) . ?
C15 N6 1.347(4) . ?
C15 N7 1.326(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.348(5) . ?
C16 N6 1.385(4) . ?
C16 H16 0.9300 . ?
C17 N7 1.380(4) . ?
C17 H17 0.9300 . ?
C18 O10 1.227(4) . ?
C18 O9 1.282(4) . ?
C18 C19 1.520(4) . ?
C19 N8 1.323(4) . ?
C19 C20 1.378(5) . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.411(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 N8 1.329(4) . ?
C23 C24 1.526(4) . ?
C24 O8 1.218(4) . ?
C24 O7 1.293(4) . ?
Cu1 N1 1.906(2) . ?
Cu1 N2 1.937(3) . ?
Cu1 O2 2.029(2) . ?
Cu1 O4 2.036(2) . ?
Cu1 O5 2.336(3) . ?
Cu1 H2W 2.67(4) . ?
Cu2 N8 1.907(3) . ?
Cu2 N7 1.944(3) . ?
Cu2 O7 2.044(2) . ?
Cu2 O9 2.051(2) . ?
Cu2 O6 2.311(3) . ?
Cu2 H4W 2.78(3) . ?
N4 N5 1.353(4) . ?
O5 H1W 0.837(19) . ?
O5 H2W 0.827(19) . ?
O6 H3W 0.838(19) . ?
O6 H4W 0.841(19) . ?

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 C1 O4 125.6(3) . . ?
O3 C1 C2 120.5(3) . . ?
O4 C1 C2 113.9(2) . . ?
N1 C2 C3 120.1(3) . . ?
N1 C2 C1 111.9(3) . . ?
C3 C2 C1 128.0(3) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 120.7(3) . . ?
N1 C6 C7 111.7(3) . . ?
C5 C6 C7 127.7(3) . . ?
O1 C7 O2 126.0(3) . . ?
O1 C7 C6 119.7(3) . . ?
O2 C7 C6 114.3(3) . . ?
N2 C8 N3 110.3(3) . . ?
N2 C8 H8 124.9 . . ?
N3 C8 H8 124.9 . . ?
C10 C9 N2 110.0(3) . . ?
C10 C9 H9 125.0 . . ?
N2 C9 H9 125.0 . . ?
C9 C10 N3 106.6(3) . . ?
C9 C10 H10 126.7 . . ?
N3 C10 H10 126.7 . . ?
N4 C11 N3 115.0(2) . . ?
N4 C11 C12 124.4(3) . . ?
N3 C11 C12 120.5(3) . . ?
C13 C12 C11 116.1(3) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C14 C13 C12 117.8(3) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
N5 C14 C13 123.6(3) . . ?
N5 C14 N6 114.8(3) . . ?
C13 C14 N6 121.7(3) . . ?
N6 C15 N7 110.4(3) . . ?
N6 C15 H15 124.8 . . ?
N7 C15 H15 124.8 . . ?
C17 C16 N6 106.2(3) . . ?
C17 C16 H16 126.9 . . ?
N6 C16 H16 126.9 . . ?
C16 C17 N7 109.5(3) . . ?
C16 C17 H17 125.3 . . ?
N7 C17 H17 125.3 . . ?
O10 C18 O9 126.2(3) . . ?
O10 C18 C19 118.9(3) . . ?
O9 C18 C19 114.9(3) . . ?
N8 C19 C20 120.8(3) . . ?
N8 C19 C18 112.1(3) . . ?
C20 C19 C18 127.1(3) . . ?
C19 C20 C21 118.2(3) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 117.2(3) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
N8 C23 C22 120.9(3) . . ?
N8 C23 C24 112.3(3) . . ?
C22 C23 C24 126.8(3) . . ?
O8 C24 O7 126.9(3) . . ?
O8 C24 C23 119.7(3) . . ?
O7 C24 C23 113.4(3) . . ?
N1 Cu1 N2 174.16(10) . . ?
N1 Cu1 O2 80.52(10) . . ?
N2 Cu1 O2 98.28(10) . . ?
N1 Cu1 O4 80.12(9) . . ?
N2 Cu1 O4 100.49(10) . . ?
O2 Cu1 O4 160.02(9) . . ?
N1 Cu1 O5 92.70(10) . . ?
N2 Cu1 O5 93.07(10) . . ?
O2 Cu1 O5 92.88(10) . . ?
O4 Cu1 O5 92.92(9) . . ?
N1 Cu1 H2W 84.2(9) . . ?
N2 Cu1 H2W 101.1(9) . . ?
O2 Cu1 H2W 76.5(7) . . ?
O4 Cu1 H2W 106.4(8) . . ?
O5 Cu1 H2W 17.4(6) . . ?
N8 Cu2 N7 171.36(10) . . ?
N8 Cu2 O7 80.14(10) . . ?
N7 Cu2 O7 99.81(10) . . ?
N8 Cu2 O9 80.42(10) . . ?
N7 Cu2 O9 99.05(10) . . ?
O7 Cu2 O9 160.42(9) . . ?
N8 Cu2 O6 93.53(10) . . ?
N7 Cu2 O6 95.11(10) . . ?
O7 Cu2 O6 90.26(9) . . ?
O9 Cu2 O6 93.28(9) . . ?
N8 Cu2 H4W 94.7(9) . . ?
N7 Cu2 H4W 93.7(9) . . ?
O7 Cu2 H4W 105.9(7) . . ?
O9 Cu2 H4W 78.0(7) . . ?
O6 Cu2 H4W 15.7(7) . . ?
C6 N1 C2 122.6(3) . . ?
C6 N1 Cu1 118.5(2) . . ?
C2 N1 Cu1 118.8(2) . . ?
C8 N2 C9 105.9(3) . . ?
C8 N2 Cu1 128.5(2) . . ?
C9 N2 Cu1 125.1(2) . . ?
C10 N3 C8 107.2(2) . . ?
C10 N3 C11 127.5(3) . . ?
C8 N3 C11 125.3(3) . . ?
C11 N4 N5 119.2(3) . . ?
C14 N5 N4 118.9(3) . . ?
C15 N6 C16 107.5(3) . . ?
C15 N6 C14 126.3(3) . . ?
C16 N6 C14 126.0(3) . . ?
C15 N7 C17 106.4(3) . . ?
C15 N7 Cu2 126.2(2) . . ?
C17 N7 Cu2 127.1(2) . . ?
C23 N8 C19 122.3(3) . . ?
C23 N8 Cu2 118.9(2) . . ?
C19 N8 Cu2 118.7(2) . . ?
C7 O2 Cu1 114.84(19) . . ?
C1 O4 Cu1 114.91(18) . . ?
Cu1 O5 H1W 109(3) . . ?
Cu1 O5 H2W 105(3) . . ?
H1W O5 H2W 102(4) . . ?
Cu2 O6 H3W 110(3) . . ?
Cu2 O6 H4W 116(3) . . ?
H3W O6 H4W 104(4) . . ?
C24 O7 Cu2 114.93(19) . . ?
C18 O9 Cu2 113.9(2) . . ?

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
O3 C1 C2 N1 -176.9(3) . . . . ?
O4 C1 C2 N1 3.2(4) . . . . ?
O3 C1 C2 C3 4.2(5) . . . . ?
O4 C1 C2 C3 -175.8(3) . . . . ?
N1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C4 C5 C6 N1 -0.7(5) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
N1 C6 C7 O1 177.4(3) . . . . ?
C5 C6 C7 O1 -2.3(5) . . . . ?
N1 C6 C7 O2 -2.7(4) . . . . ?
C5 C6 C7 O2 177.6(3) . . . . ?
N2 C9 C10 N3 0.0(4) . . . . ?
N4 C11 C12 C13 -0.9(5) . . . . ?
N3 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C12 C13 C14 N5 2.3(5) . . . . ?
C12 C13 C14 N6 -177.7(3) . . . . ?
N6 C16 C17 N7 -0.9(4) . . . . ?
O10 C18 C19 N8 179.8(3) . . . . ?
O9 C18 C19 N8 0.0(4) . . . . ?
O10 C18 C19 C20 -0.5(5) . . . . ?
O9 C18 C19 C20 179.7(3) . . . . ?
N8 C19 C20 C21 0.3(5) . . . . ?
C18 C19 C20 C21 -179.4(3) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -0.9(5) . . . . ?
C21 C22 C23 N8 0.2(4) . . . . ?
C21 C22 C23 C24 180.0(3) . . . . ?
N8 C23 C24 O8 -173.7(3) . . . . ?
C22 C23 C24 O8 6.6(5) . . . . ?
N8 C23 C24 O7 5.4(4) . . . . ?
C22 C23 C24 O7 -174.4(3) . . . . ?
C5 C6 N1 C2 -0.7(5) . . . . ?
C7 C6 N1 C2 179.5(3) . . . . ?
C5 C6 N1 Cu1 -179.6(2) . . . . ?
C7 C6 N1 Cu1 0.7(3) . . . . ?
C3 C2 N1 C6 1.3(4) . . . . ?
C1 C2 N1 C6 -177.8(2) . . . . ?
C3 C2 N1 Cu1 -179.9(2) . . . . ?
C1 C2 N1 Cu1 1.1(3) . . . . ?
N3 C8 N2 C9 -0.4(4) . . . . ?
N3 C8 N2 Cu1 171.6(2) . . . . ?
C10 C9 N2 C8 0.2(4) . . . . ?
C10 C9 N2 Cu1 -172.2(2) . . . . ?
C9 C10 N3 C8 -0.3(3) . . . . ?
C9 C10 N3 C11 177.9(3) . . . . ?
N2 C8 N3 C10 0.4(4) . . . . ?
N2 C8 N3 C11 -177.8(3) . . . . ?
N4 C11 N3 C10 175.1(3) . . . . ?
C12 C11 N3 C10 -5.9(5) . . . . ?
N4 C11 N3 C8 -7.0(4) . . . . ?
C12 C11 N3 C8 172.0(3) . . . . ?
N3 C11 N4 N5 -178.9(3) . . . . ?
C12 C11 N4 N5 2.2(5) . . . . ?
C13 C14 N5 N4 -1.1(5) . . . . ?
N6 C14 N5 N4 179.0(3) . . . . ?
C11 N4 N5 C14 -1.2(5) . . . . ?
N7 C15 N6 C16 0.4(3) . . . . ?
N7 C15 N6 C14 174.6(3) . . . . ?
C17 C16 N6 C15 0.4(4) . . . . ?
C17 C16 N6 C14 -173.9(3) . . . . ?
N5 C14 N6 C15 -165.3(3) . . . . ?
C13 C14 N6 C15 14.8(5) . . . . ?
N5 C14 N6 C16 8.0(4) . . . . ?
C13 C14 N6 C16 -172.0(3) . . . . ?
N6 C15 N7 C17 -0.9(3) . . . . ?
N6 C15 N7 Cu2 -174.68(19) . . . . ?
C16 C17 N7 C15 1.2(4) . . . . ?
C16 C17 N7 Cu2 174.8(2) . . . . ?
C22 C23 N8 C19 0.7(4) . . . . ?
C24 C23 N8 C19 -179.1(3) . . . . ?
C22 C23 N8 Cu2 178.3(2) . . . . ?
C24 C23 N8 Cu2 -1.5(3) . . . . ?
C20 C19 N8 C23 -1.0(4) . . . . ?
C18 C19 N8 C23 178.8(3) . . . . ?
C20 C19 N8 Cu2 -178.6(2) . . . . ?
C18 C19 N8 Cu2 1.2(3) . . . . ?
O1 C7 O2 Cu1 -176.8(3) . . . . ?
C6 C7 O2 Cu1 3.3(3) . . . . ?
O3 C1 O4 Cu1 174.4(2) . . . . ?
C2 C1 O4 Cu1 -5.6(3) . . . . ?
O8 C24 O7 Cu2 172.4(3) . . . . ?
C23 C24 O7 Cu2 -6.6(3) . . . . ?
O10 C18 O9 Cu2 179.2(3) . . . . ?
C19 C18 O9 Cu2 -1.1(3) . . . . ?

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
O6 H3W O4 0.838(19) 1.95(3) 2.735(3) 156(4) 2_766

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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 1527999'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Co N6 O14'
_chemical_formula_weight         725.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.5905(5)
_cell_length_b                   11.7646(5)
_cell_length_c                   13.5378(6)
_cell_angle_alpha                105.3360(10)
_cell_angle_beta                 105.4280(10)
_cell_angle_gamma                106.8560(10)
_cell_volume                     1445.46(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.18

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             742
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.681
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9549
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.680
_diffrn_reflns_theta_max         25.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5219
_reflns_number_gt                4028
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0592P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5219
_refine_ls_number_parameters     490
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.977
_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
C19A C 0.7199(7) -0.0094(7) -0.1630(3) 0.0388(16) Uani 0.658(13) 1 d D U P A 1
H19A H 0.7379 -0.0474 -0.2245 0.047 Uiso 0.658(13) 1 calc R U P A 1
C18A C 0.6176(7) 0.0366(8) -0.1649(3) 0.0384(15) Uani 0.658(13) 1 d D U P A 1
H18A H 0.5517 0.0355 -0.2267 0.046 Uiso 0.658(13) 1 calc R U P A 1
C19B C 0.6775(11) -0.0655(13) -0.1537(7) 0.045(3) Uani 0.342(13) 1 d D U P A 2
H19B H 0.6705 -0.1359 -0.2094 0.054 Uiso 0.342(13) 1 calc R U P A 2
C18B C 0.5771(11) -0.0173(12) -0.1547(7) 0.044(3) Uani 0.342(13) 1 d D U P A 2
H18B H 0.4890 -0.0474 -0.2110 0.053 Uiso 0.342(13) 1 calc R U P A 2
C1 C 0.1599(3) 0.7344(3) 0.6518(2) 0.0272(6) Uani 1 1 d . . . . .
C2 C 0.1737(3) 0.7672(2) 0.5554(2) 0.0246(6) Uani 1 1 d . . . . .
C3 C 0.2519(3) 0.8916(2) 0.5700(2) 0.0248(6) Uani 1 1 d . . . . .
H3 H 0.2939 0.9553 0.6400 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2672(3) 0.9206(2) 0.4803(2) 0.0245(6) Uani 1 1 d . . . . .
C5 C 0.1999(3) 0.8259(2) 0.3742(2) 0.0246(6) Uani 1 1 d . . . . .
H5 H 0.2093 0.8460 0.3139 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1193(3) 0.7023(2) 0.35933(19) 0.0223(5) Uani 1 1 d . . . . .
C7 C 0.1082(3) 0.6732(2) 0.4501(2) 0.0252(6) Uani 1 1 d . . . . .
H7 H 0.0562 0.5897 0.4404 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3595(3) 1.0511(2) 0.4966(2) 0.0272(6) Uani 1 1 d . . . . .
C9 C 0.0466(3) 0.5976(2) 0.24557(19) 0.0224(5) Uani 1 1 d . . . . .
C10 C 0.3211(3) 0.5766(3) 0.1185(2) 0.0318(6) Uani 1 1 d . . . . .
H10 H 0.3289 0.6549 0.1642 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4251(3) 0.5321(3) 0.1298(2) 0.0349(7) Uani 1 1 d . . . . .
H11 H 0.5164 0.5727 0.1834 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2337(3) 0.3935(3) -0.0127(2) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.1719 0.3210 -0.0746 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4401(3) 0.3288(3) 0.0274(2) 0.0258(6) Uani 1 1 d . . . . .
C14 C 0.5687(3) 0.3522(3) 0.1080(2) 0.0390(8) Uani 1 1 d . . . . .
H14 H 0.6089 0.4210 0.1750 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6313(3) 0.2692(3) 0.0832(2) 0.0380(7) Uani 1 1 d . . . . .
H15 H 0.7164 0.2781 0.1332 0.046 Uiso 1 1 calc R U . . .
C16 C 0.5644(3) 0.1700(3) -0.0195(2) 0.0273(6) Uani 1 1 d . . . . .
C17 C 0.7468(3) 0.0764(2) 0.0069(2) 0.0252(6) Uani 1 1 d D U . . .
H17 H 0.7869 0.1133 0.0835 0.030 Uiso 1 1 calc R U . . .
C20 C 1.0860(3) 0.1687(2) 0.18733(19) 0.0209(5) Uani 1 1 d . . . . .
C21 C 1.1563(3) 0.2645(2) 0.30324(19) 0.0214(5) Uani 1 1 d . . . . .
C22 C 1.1418(3) 0.2270(2) 0.39042(19) 0.0231(5) Uani 1 1 d . . . . .
H22 H 1.0873 0.1426 0.3763 0.028 Uiso 1 1 calc R U . . .
C23 C 1.2082(3) 0.3150(2) 0.49823(19) 0.0235(6) Uani 1 1 d . . . . .
C24 C 1.2924(3) 0.4408(2) 0.5195(2) 0.0247(6) Uani 1 1 d . . . . .
H24 H 1.3376 0.4999 0.5916 0.030 Uiso 1 1 calc R U . . .
C25 C 1.3088(3) 0.4778(2) 0.43351(19) 0.0237(6) Uani 1 1 d . . . . .
C26 C 1.2405(3) 0.3896(2) 0.3250(2) 0.0239(6) Uani 1 1 d . . . . .
H26 H 1.2516 0.4149 0.2673 0.029 Uiso 1 1 calc R U . . .
C27 C 1.4019(3) 0.6105(2) 0.4548(2) 0.0262(6) Uani 1 1 d . . . . .
C28 C 1.1953(3) 0.2783(3) 0.5940(2) 0.0261(6) Uani 1 1 d . . . . .
Co1 Co 0.0000 0.5000 0.0000 0.01843(13) Uani 1 2 d S . P . .
Co2 Co 1.0000 0.0000 0.0000 0.01938(14) Uani 1 2 d S . P A .
N1 N 0.2015(2) 0.4898(2) 0.03012(17) 0.0255(5) Uani 1 1 d . . . . .
N2 N 0.3692(2) 0.4136(2) 0.04534(17) 0.0266(5) Uani 1 1 d . . . . .
N3 N 0.3787(2) 0.2325(2) -0.06783(19) 0.0315(5) Uani 1 1 d . . . . .
N4 N 0.4416(2) 0.1500(2) -0.09213(19) 0.0331(6) Uani 1 1 d . . . . .
N5 N 0.6300(2) 0.0864(2) -0.05527(17) 0.0305(5) Uani 1 1 d D U . . .
N6 N 0.7962(2) 0.0088(2) -0.05357(17) 0.0334(6) Uani 1 1 d D U . . .
O1 O 0.1907(2) 0.81240(19) 0.74109(15) 0.0412(5) Uani 1 1 d . . . . .
O2 O 0.1113(3) 0.6107(2) 0.62850(16) 0.0564(7) Uani 1 1 d D . . . .
H1O H 0.102(4) 0.588(3) 0.680(2) 0.068 Uiso 1 1 d D U . . .
O3 O 0.4245(2) 1.12982(19) 0.59823(16) 0.0462(6) Uani 1 1 d D . . . .
H2O H 0.481(3) 1.202(2) 0.603(3) 0.055 Uiso 1 1 d D U . . .
O4 O 0.3730(2) 1.08056(19) 0.41814(15) 0.0446(6) Uani 1 1 d . . . . .
O5 O 0.06733(19) 0.62503(16) 0.16657(13) 0.0247(4) Uani 1 1 d . . . . .
O6 O -0.0288(2) 0.48767(17) 0.23712(14) 0.0346(5) Uani 1 1 d . . . . .
O7 O 0.0710(2) 0.66134(18) -0.04024(16) 0.0297(4) Uani 1 1 d D . . . .
H1W H 0.007(3) 0.692(4) -0.052(3) 0.089(15) Uiso 1 1 d D . . . .
H2W H 0.063(4) 0.626(3) -0.1069(17) 0.069(12) Uiso 1 1 d D . . . .
O8 O 1.2538(2) 0.35364(19) 0.68838(14) 0.0402(5) Uani 1 1 d . . . . .
O9 O 1.1138(2) 0.15777(19) 0.56419(15) 0.0377(5) Uani 1 1 d D . . . .
H3O H 1.108(3) 0.138(3) 0.618(2) 0.045 Uiso 1 1 d D U . . .
O10 O 1.4611(2) 0.68789(18) 0.55681(15) 0.0383(5) Uani 1 1 d D . . . .
H4O H 1.511(3) 0.761(2) 0.567(3) 0.046 Uiso 1 1 d D U . . .
O11 O 1.4186(2) 0.64157(19) 0.37749(16) 0.0422(5) Uani 1 1 d . . . . .
O12 O 1.09918(19) 0.20240(16) 0.10807(13) 0.0251(4) Uani 1 1 d . . . . .
O13 O 1.01718(19) 0.05331(16) 0.16837(13) 0.0252(4) Uani 1 1 d . . . . .
O14 O 0.1129(3) 0.1150(2) 0.74396(18) 0.0556(7) Uani 1 1 d D . . . .
H3W H 0.184(3) 0.157(3) 0.799(2) 0.083 Uiso 1 1 d D U . . .
H4W H 0.076(4) 0.050(3) 0.755(3) 0.083 Uiso 1 1 d D 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
C19A C18A 1.342(5) . ?
C19A N6 1.410(4) . ?
C18A N5 1.398(4) . ?
C19B C18B 1.341(8) . ?
C19B N6 1.418(6) . ?
C18B N5 1.396(6) . ?
C1 O1 1.200(3) . ?
C1 O2 1.311(3) . ?
C1 C2 1.487(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.390(3) . ?
C3 C4 1.382(4) . ?
C4 C5 1.400(3) . ?
C4 C8 1.482(4) . ?
C5 C6 1.385(4) . ?
C6 C7 1.384(3) . ?
C6 C9 1.516(3) . ?
C8 O4 1.232(3) . ?
C8 O3 1.295(3) . ?
C9 O5 1.250(3) . ?
C9 O6 1.264(3) . ?
C10 C11 1.341(4) . ?
C10 N1 1.370(3) . ?
C11 N2 1.385(3) . ?
C12 N1 1.310(3) . ?
C12 N2 1.355(3) . ?
C13 N3 1.312(3) . ?
C13 C14 1.398(4) . ?
C13 N2 1.422(3) . ?
C14 C15 1.351(4) . ?
C15 C16 1.391(4) . ?
C16 N4 1.316(3) . ?
C16 N5 1.417(3) . ?
C17 N6 1.304(3) . ?
C17 N5 1.354(3) . ?
C20 O13 1.258(3) . ?
C20 O12 1.265(3) . ?
C20 C21 1.498(3) . ?
C20 Co2 2.502(2) . ?
C21 C26 1.384(4) . ?
C21 C22 1.394(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.393(4) . ?
C23 C28 1.498(3) . ?
C24 C25 1.381(4) . ?
C25 C26 1.397(3) . ?
C25 C27 1.487(4) . ?
C27 O11 1.234(3) . ?
C27 O10 1.294(3) . ?
C28 O8 1.210(3) . ?
C28 O9 1.311(3) . ?
Co1 O7 2.0981(18) 2_565 ?
Co1 O7 2.0981(18) . ?
Co1 N1 2.109(2) . ?
Co1 N1 2.109(2) 2_565 ?
Co1 O5 2.1304(16) . ?
Co1 O5 2.1304(16) 2_565 ?
Co2 N6 2.129(2) . ?
Co2 N6 2.129(2) 2_755 ?
Co2 O13 2.1398(16) 2_755 ?
Co2 O13 2.1398(16) . ?
Co2 O12 2.1916(16) . ?
Co2 O12 2.1916(16) 2_755 ?
Co2 C20 2.502(2) 2_755 ?
N3 N4 1.348(3) . ?

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
C18A C19A N6 109.6(3) . . ?
C19A C18A N5 106.1(3) . . ?
C18B C19B N6 108.7(5) . . ?
C19B C18B N5 107.0(5) . . ?
O1 C1 O2 123.8(2) . . ?
O1 C1 C2 123.8(2) . . ?
O2 C1 C2 112.4(2) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 120.2(2) . . ?
C7 C2 C1 120.1(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 C8 120.0(2) . . ?
C5 C4 C8 119.7(2) . . ?
C6 C5 C4 119.9(2) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 C9 119.5(2) . . ?
C5 C6 C9 121.0(2) . . ?
C6 C7 C2 120.8(2) . . ?
O4 C8 O3 123.2(3) . . ?
O4 C8 C4 121.5(2) . . ?
O3 C8 C4 115.3(2) . . ?
O5 C9 O6 124.3(2) . . ?
O5 C9 C6 117.8(2) . . ?
O6 C9 C6 117.9(2) . . ?
C11 C10 N1 110.1(2) . . ?
C10 C11 N2 106.1(2) . . ?
N1 C12 N2 111.0(2) . . ?
N3 C13 C14 124.1(2) . . ?
N3 C13 N2 115.9(2) . . ?
C14 C13 N2 119.9(2) . . ?
C15 C14 C13 116.2(3) . . ?
C14 C15 C16 118.0(2) . . ?
N4 C16 C15 123.8(2) . . ?
N4 C16 N5 115.1(2) . . ?
C15 C16 N5 121.1(2) . . ?
N6 C17 N5 111.9(2) . . ?
O13 C20 O12 119.5(2) . . ?
O13 C20 C21 120.3(2) . . ?
O12 C20 C21 120.2(2) . . ?
O13 C20 Co2 58.77(12) . . ?
O12 C20 Co2 61.12(12) . . ?
C21 C20 Co2 171.48(16) . . ?
C26 C21 C22 119.5(2) . . ?
C26 C21 C20 120.3(2) . . ?
C22 C21 C20 120.1(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 C28 121.9(2) . . ?
C24 C23 C28 118.3(2) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 C27 120.8(2) . . ?
C26 C25 C27 119.0(2) . . ?
C21 C26 C25 120.1(2) . . ?
O11 C27 O10 123.8(2) . . ?
O11 C27 C25 120.3(2) . . ?
O10 C27 C25 116.0(2) . . ?
O8 C28 O9 124.5(2) . . ?
O8 C28 C23 122.6(2) . . ?
O9 C28 C23 113.0(2) . . ?
O7 Co1 O7 180.00(13) 2_565 . ?
O7 Co1 N1 90.15(8) 2_565 . ?
O7 Co1 N1 89.85(8) . . ?
O7 Co1 N1 89.85(8) 2_565 2_565 ?
O7 Co1 N1 90.15(8) . 2_565 ?
N1 Co1 N1 180.0 . 2_565 ?
O7 Co1 O5 91.52(7) 2_565 . ?
O7 Co1 O5 88.48(7) . . ?
N1 Co1 O5 90.84(7) . . ?
N1 Co1 O5 89.16(7) 2_565 . ?
O7 Co1 O5 88.48(7) 2_565 2_565 ?
O7 Co1 O5 91.52(7) . 2_565 ?
N1 Co1 O5 89.16(7) . 2_565 ?
N1 Co1 O5 90.84(7) 2_565 2_565 ?
O5 Co1 O5 180.0 . 2_565 ?
N6 Co2 N6 180.0 . 2_755 ?
N6 Co2 O13 87.58(7) . 2_755 ?
N6 Co2 O13 92.41(7) 2_755 2_755 ?
N6 Co2 O13 92.42(7) . . ?
N6 Co2 O13 87.59(7) 2_755 . ?
O13 Co2 O13 180.00(16) 2_755 . ?
N6 Co2 O12 92.00(7) . . ?
N6 Co2 O12 88.00(7) 2_755 . ?
O13 Co2 O12 119.61(6) 2_755 . ?
O13 Co2 O12 60.40(6) . . ?
N6 Co2 O12 88.00(7) . 2_755 ?
N6 Co2 O12 92.00(7) 2_755 2_755 ?
O13 Co2 O12 60.40(6) 2_755 2_755 ?
O13 Co2 O12 119.60(6) . 2_755 ?
O12 Co2 O12 180.0 . 2_755 ?
N6 Co2 C20 94.75(8) . . ?
N6 Co2 C20 85.25(8) 2_755 . ?
O13 Co2 C20 149.83(7) 2_755 . ?
O13 Co2 C20 30.17(7) . . ?
O12 Co2 C20 30.37(7) . . ?
O12 Co2 C20 149.63(7) 2_755 . ?
N6 Co2 C20 85.25(8) . 2_755 ?
N6 Co2 C20 94.75(8) 2_755 2_755 ?
O13 Co2 C20 30.17(7) 2_755 2_755 ?
O13 Co2 C20 149.83(7) . 2_755 ?
O12 Co2 C20 149.63(7) . 2_755 ?
O12 Co2 C20 30.37(7) 2_755 2_755 ?
C20 Co2 C20 180.0 . 2_755 ?
C12 N1 C10 106.3(2) . . ?
C12 N1 Co1 128.92(18) . . ?
C10 N1 Co1 123.41(17) . . ?
C12 N2 C11 106.6(2) . . ?
C12 N2 C13 127.5(2) . . ?
C11 N2 C13 125.9(2) . . ?
C13 N3 N4 119.4(2) . . ?
C16 N4 N3 118.6(2) . . ?
C17 N5 C18B 104.2(4) . . ?
C17 N5 C18A 106.4(3) . . ?
C17 N5 C16 126.9(2) . . ?
C18B N5 C16 128.1(4) . . ?
C18A N5 C16 123.1(3) . . ?
C17 N6 C19B 103.4(4) . . ?
C17 N6 C19A 105.1(3) . . ?
C17 N6 Co2 126.00(17) . . ?
C19B N6 Co2 130.1(4) . . ?
C19A N6 Co2 124.0(3) . . ?
C9 O5 Co1 128.16(16) . . ?
C20 O12 Co2 88.51(14) . . ?
C20 O13 Co2 91.06(14) . . ?

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
N6 C19A C18A N5 0.9(6) . . . . ?
N6 C19B C18B N5 -0.7(13) . . . . ?
O1 C1 C2 C3 13.9(4) . . . . ?
O2 C1 C2 C3 -165.7(3) . . . . ?
O1 C1 C2 C7 -166.0(3) . . . . ?
O2 C1 C2 C7 14.4(4) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C1 C2 C3 C4 178.4(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C2 C3 C4 C8 -175.4(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C8 C4 C5 C6 176.8(2) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C6 C9 -179.3(2) . . . . ?
C5 C6 C7 C2 1.8(4) . . . . ?
C9 C6 C7 C2 179.9(2) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 179.6(2) . . . . ?
C3 C4 C8 O4 -178.5(3) . . . . ?
C5 C4 C8 O4 3.8(4) . . . . ?
C3 C4 C8 O3 2.0(4) . . . . ?
C5 C4 C8 O3 -175.7(2) . . . . ?
C7 C6 C9 O5 -174.8(2) . . . . ?
C5 C6 C9 O5 3.3(4) . . . . ?
C7 C6 C9 O6 3.9(4) . . . . ?
C5 C6 C9 O6 -178.0(2) . . . . ?
N1 C10 C11 N2 0.2(3) . . . . ?
N3 C13 C14 C15 0.6(5) . . . . ?
N2 C13 C14 C15 -178.1(3) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 N4 -2.3(5) . . . . ?
C14 C15 C16 N5 174.2(3) . . . . ?
O13 C20 C21 C26 175.4(2) . . . . ?
O12 C20 C21 C26 -2.3(3) . . . . ?
O13 C20 C21 C22 -2.2(3) . . . . ?
O12 C20 C21 C22 -179.9(2) . . . . ?
C26 C21 C22 C23 1.6(4) . . . . ?
C20 C21 C22 C23 179.2(2) . . . . ?
C21 C22 C23 C24 -1.5(4) . . . . ?
C21 C22 C23 C28 -179.9(2) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C28 C23 C24 C25 179.0(2) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C23 C24 C25 C27 -178.0(2) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
C20 C21 C26 C25 -178.4(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C27 C25 C26 C21 178.2(2) . . . . ?
C24 C25 C27 O11 178.1(2) . . . . ?
C26 C25 C27 O11 -0.3(4) . . . . ?
C24 C25 C27 O10 -2.2(4) . . . . ?
C26 C25 C27 O10 179.5(2) . . . . ?
C22 C23 C28 O8 179.2(2) . . . . ?
C24 C23 C28 O8 0.8(4) . . . . ?
C22 C23 C28 O9 -1.4(4) . . . . ?
C24 C23 C28 O9 -179.8(2) . . . . ?
N2 C12 N1 C10 0.8(3) . . . . ?
N2 C12 N1 Co1 -165.80(17) . . . . ?
C11 C10 N1 C12 -0.6(3) . . . . ?
C11 C10 N1 Co1 166.9(2) . . . . ?
N1 C12 N2 C11 -0.7(3) . . . . ?
N1 C12 N2 C13 176.9(2) . . . . ?
C10 C11 N2 C12 0.3(3) . . . . ?
C10 C11 N2 C13 -177.3(3) . . . . ?
N3 C13 N2 C12 14.8(4) . . . . ?
C14 C13 N2 C12 -166.4(3) . . . . ?
N3 C13 N2 C11 -168.1(3) . . . . ?
C14 C13 N2 C11 10.7(4) . . . . ?
C14 C13 N3 N4 -0.7(4) . . . . ?
N2 C13 N3 N4 178.1(2) . . . . ?
C15 C16 N4 N3 2.3(4) . . . . ?
N5 C16 N4 N3 -174.4(2) . . . . ?
C13 N3 N4 C16 -0.8(4) . . . . ?
N6 C17 N5 C18B 21.8(8) . . . . ?
N6 C17 N5 C18A -9.3(5) . . . . ?
N6 C17 N5 C16 -168.0(3) . . . . ?
C19B C18B N5 C17 -11.9(11) . . . . ?
C19B C18B N5 C16 178.1(7) . . . . ?
C19A C18A N5 C17 4.8(5) . . . . ?
C19A C18A N5 C16 164.4(4) . . . . ?
N4 C16 N5 C17 -171.6(3) . . . . ?
C15 C16 N5 C17 11.6(4) . . . . ?
N4 C16 N5 C18B -3.7(11) . . . . ?
C15 C16 N5 C18B 179.5(10) . . . . ?
N4 C16 N5 C18A 33.0(6) . . . . ?
C15 C16 N5 C18A -143.8(5) . . . . ?
N5 C17 N6 C19B -21.9(8) . . . . ?
N5 C17 N6 C19A 9.6(5) . . . . ?
N5 C17 N6 Co2 165.36(19) . . . . ?
C18B C19B N6 C17 13.4(11) . . . . ?
C18B C19B N6 Co2 -174.2(7) . . . . ?
C18A C19A N6 C17 -6.4(6) . . . . ?
C18A C19A N6 Co2 -162.7(4) . . . . ?
O6 C9 O5 Co1 -5.0(4) . . . . ?
C6 C9 O5 Co1 173.62(14) . . . . ?
O13 C20 O12 Co2 -7.4(2) . . . . ?
C21 C20 O12 Co2 170.33(19) . . . . ?
O12 C20 O13 Co2 7.6(2) . . . . ?
C21 C20 O13 Co2 -170.15(19) . . . . ?

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
C19A H19A O4 0.93 2.44 3.127(4) 130.7 2_665
C19A H19A O13 0.93 2.53 2.991(6) 111.0 2_755
C11 H11 O8 0.93 2.33 3.252(3) 172.1 2_766
C14 H14 O8 0.93 2.51 3.396(4) 159.1 2_766
C15 H15 O1 0.93 2.38 3.164(3) 141.5 2_666
C17 H17 O1 0.93 2.22 3.119(3) 161.4 2_666
O2 H1O O6 0.827(19) 1.80(2) 2.605(3) 163(4) 2_566
O3 H2O O11 0.859(18) 1.745(19) 2.599(3) 172(3) 2_776
O7 H1W O12 0.856(19) 2.06(2) 2.869(2) 158(4) 2_665
O7 H2W O6 0.858(18) 1.78(2) 2.611(3) 163(4) 2_565
O9 H3O O14 0.837(18) 1.781(18) 2.614(3) 173(3) 1_655
O10 H4O O4 0.825(18) 1.830(18) 2.654(3) 176(3) 2_776
O14 H3W N3 0.811(19) 2.10(2) 2.896(3) 169(4) 1_556
O14 H4W O13 0.827(19) 2.01(2) 2.785(3) 157(4) 2_656

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064

