# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1813159'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C26 H40 Cu4 N10 O19'
_chemical_formula_weight         1050.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   11.1999(18)
_cell_length_b                   17.297(3)
_cell_length_c                   14.0431(19)
_cell_angle_alpha                90
_cell_angle_beta                 124.762(9)
_cell_angle_gamma                90
_cell_volume                     2235.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7757
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.29

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.956
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34181
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.908
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3937
_reflns_number_gt                2945
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0427P)²+9.2245P] 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         3937
_refine_ls_number_parameters     322
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.100
_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
Cu1 Cu 0.89661(7) 0.64854(4) 0.50700(5) 0.02013(19) Uani 1 1 d . . . . .
Cu2 Cu 1.14058(7) 0.51842(3) 0.61392(5) 0.01841(18) Uani 1 1 d . . . . .
O1 O 0.9226(4) 0.5377(2) 0.5274(3) 0.0171(9) Uani 1 1 d . . . . .
H1 H 0.889(7) 0.526(4) 0.549(6) 0.026 Uiso 1 1 d . U . . .
O2 O 0.8641(5) 0.7593(2) 0.4837(4) 0.0449(12) Uani 1 1 d . . . . .
O3 O 0.2472(4) 0.8910(2) 0.0897(3) 0.0334(10) Uani 1 1 d . . . . .
O4 O 0.0304(4) 0.8573(2) -0.0649(3) 0.0300(9) Uani 1 1 d . . . . .
O5 O 0.0356(4) 0.6698(2) -0.3288(3) 0.0356(11) Uani 1 1 d . . . . .
O6 O 0.1837(4) 0.5674(2) -0.2471(3) 0.0273(9) Uani 1 1 d . . . . .
O7 O 0.4106(13) 0.5798(9) 0.3858(13) 0.100(5) Uani 0.5 1 d D . P . .
O8 O 0.220(3) 0.6533(16) 0.205(2) 0.061(8) Uani 0.25 1 d . U P . .
O8' O 0.163(3) 0.6402(15) 0.162(2) 0.063(8) Uani 0.25 1 d . U P . .
O9 O 0.253(3) 0.5955(12) 0.288(3) 0.053(6) Uani 0.25 1 d . . P . .
O9' O 0.164(3) 0.5828(14) 0.2394(19) 0.040(6) Uani 0.25 1 d . U P . .
O10 O 0.9989(14) 0.9405(8) 0.6902(11) 0.084(4) Uani 0.5 1 d . . P . .
O11 O 0.2175(9) 0.4977(4) 0.3711(7) 0.102(2) Uani 1 1 d . . . . .
O12 O 0.1560(19) 0.5530(13) 0.2799(19) 0.045(5) Uani 0.25 1 d D U P . .
O12' O 0.271(3) 0.5517(14) 0.3400(19) 0.054(5) Uani 0.25 1 d . U P . .
N1 N 0.6159(5) 0.6792(3) 0.2790(4) 0.0260(11) Uani 1 1 d . . . . .
N2 N 0.7208(5) 0.6298(2) 0.3491(4) 0.0228(10) Uani 1 1 d . . . . .
N3 N 0.7082(5) 0.5662(2) 0.2928(3) 0.0204(10) Uani 1 1 d . . . . .
N4 N 0.5943(5) 0.5719(2) 0.1832(4) 0.0232(11) Uani 1 1 d . . . . .
N5 N 0.7153(10) 0.8597(4) 0.3948(8) 0.103(3) Uani 1 1 d . . . . .
C1 C 0.5389(5) 0.6419(3) 0.1777(4) 0.0198(11) Uani 1 1 d . . . . .
C2 C 0.4087(5) 0.6753(3) 0.0742(4) 0.0203(12) Uani 1 1 d . . . . .
C3 C 0.3566(6) 0.7454(3) 0.0846(4) 0.0227(12) Uani 1 1 d . . . . .
H3B H 0.4085 0.7718 0.1548 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2282(6) 0.7765(3) -0.0085(4) 0.0211(12) Uani 1 1 d . . . . .
C5 C 0.1563(6) 0.7382(3) -0.1144(4) 0.0245(13) Uani 1 1 d . . . . .
H5A H 0.0704 0.7587 -0.1775 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2106(6) 0.6702(3) -0.1273(4) 0.0214(12) Uani 1 1 d . . . . .
C7 C 0.3360(6) 0.6375(3) -0.0318(4) 0.0219(12) Uani 1 1 d . . . . .
H7A H 0.3707 0.5906 -0.0392 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1638(6) 0.8478(3) 0.0058(4) 0.0225(12) Uani 1 1 d . . . . .
C9 C 0.1370(6) 0.6319(3) -0.2445(4) 0.0241(13) Uani 1 1 d . . . . .
C10 C 0.7668(11) 0.7993(5) 0.4625(9) 0.086(3) Uani 1 1 d . . . . .
C11 C 0.6897(15) 0.7813(8) 0.5233(13) 0.135(5) Uani 1 1 d . . . . .
H11B H 0.6406 0.7325 0.4963 0.202 Uiso 1 1 calc R U . . .
H11C H 0.6204 0.8212 0.5055 0.202 Uiso 1 1 calc R U . . .
H11D H 0.7606 0.7790 0.6056 0.202 Uiso 1 1 calc R U . . .
C12 C 0.789(2) 0.8670(13) 0.3251(15) 0.229(11) Uani 1 1 d . . . . .
H12A H 0.7994 0.8164 0.3024 0.343 Uiso 1 1 calc R U . . .
H12B H 0.8828 0.8907 0.3738 0.343 Uiso 1 1 calc R U . . .
H12C H 0.7285 0.8982 0.2572 0.343 Uiso 1 1 calc R U . . .
C13 C 0.6003(16) 0.9121(8) 0.3679(16) 0.211(8) Uani 1 1 d . U . . .
H13A H 0.5194 0.8833 0.3559 0.317 Uiso 1 1 calc R U . . .
H13B H 0.5701 0.9404 0.2988 0.317 Uiso 1 1 calc R U . . .
H13C H 0.6345 0.9475 0.4311 0.317 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
Cu1 O1 1.935(4) . ?
Cu1 O2 1.943(4) . ?
Cu1 O5 1.944(4) 1_656 ?
Cu1 N2 1.980(4) . ?
Cu1 O4 2.236(4) 4_676 ?
Cu1 Cu2 3.1794(9) . ?
Cu1 Cu2 3.2543(10) 3_766 ?
Cu1 H1 2.21(7) . ?
Cu2 O6 1.921(3) 1_656 ?
Cu2 O1 1.945(4) 3_766 ?
Cu2 O1 2.041(4) . ?
Cu2 N3 2.048(4) 3_766 ?
Cu2 O3 2.111(4) 4_676 ?
Cu2 Cu2 3.0117(13) 3_766 ?
Cu2 Cu1 3.2543(10) 3_766 ?
O1 Cu2 1.945(4) 3_766 ?
O1 H1 0.63(6) . ?
O2 C10 1.177(10) . ?
O3 C8 1.252(6) . ?
O3 Cu2 2.111(4) 4_475 ?
O4 C8 1.246(6) . ?
O4 Cu1 2.236(4) 4_475 ?
O5 C9 1.260(6) . ?
O5 Cu1 1.944(4) 1_454 ?
O6 C9 1.242(6) . ?
O6 Cu2 1.920(3) 1_454 ?
O7 O12' 1.39(2) . ?
O7 O9 1.52(3) . ?
O8 O8' 0.61(3) . ?
O8 O9 1.41(3) . ?
O8 O9' 1.57(4) . ?
O8' O9' 1.46(3) . ?
O8' O9 1.64(4) . ?
O9 O9' 0.86(3) . ?
O9 O12' 0.99(3) . ?
O9 O12 1.26(3) . ?
O9' O12 0.81(2) . ?
O9' O12' 1.34(3) . ?
O9' O10 1.61(3) 4_475 ?
O10 O12 1.47(2) 4_676 ?
O10 O9' 1.61(3) 4_676 ?
O11 O12' 1.31(3) . ?
O11 O12 1.42(3) . ?
O12 O12' 1.07(2) . ?
O12 O10 1.47(2) 4_475 ?
N1 N2 1.327(6) . ?
N1 C1 1.335(6) . ?
N2 N3 1.315(6) . ?
N3 N4 1.329(5) . ?
N3 Cu2 2.048(4) 3_766 ?
N4 C1 1.344(6) . ?
N5 C10 1.304(12) . ?
N5 C13 1.438(14) . ?
N5 C12 1.605(18) . ?
C1 C2 1.468(7) . ?
C2 C7 1.387(7) . ?
C2 C3 1.389(7) . ?
C3 C4 1.387(7) . ?
C3 H3B 0.9300 . ?
C4 C5 1.390(7) . ?
C4 C8 1.500(7) . ?
C5 C6 1.383(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(7) . ?
C6 C9 1.509(7) . ?
C7 H7A 0.9300 . ?
C10 C11 1.553(15) . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11D 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 178.25(18) . . ?
O1 Cu1 O5 93.45(15) . 1_656 ?
O2 Cu1 O5 87.70(16) . 1_656 ?
O1 Cu1 N2 88.48(16) . . ?
O2 Cu1 N2 90.09(17) . . ?
O5 Cu1 N2 166.25(19) 1_656 . ?
O1 Cu1 O4 86.54(15) . 4_676 ?
O2 Cu1 O4 94.45(19) . 4_676 ?
O5 Cu1 O4 104.75(17) 1_656 4_676 ?
N2 Cu1 O4 88.95(17) . 4_676 ?
O1 Cu1 Cu2 38.07(11) . . ?
O2 Cu1 Cu2 143.67(14) . . ?
O5 Cu1 Cu2 71.47(11) 1_656 . ?
N2 Cu1 Cu2 116.83(12) . . ?
O4 Cu1 Cu2 64.20(10) 4_676 . ?
O1 Cu1 Cu2 33.09(11) . 3_766 ?
O2 Cu1 Cu2 146.24(13) . 3_766 ?
O5 Cu1 Cu2 124.33(11) 1_656 3_766 ?
N2 Cu1 Cu2 61.37(12) . 3_766 ?
O4 Cu1 Cu2 69.14(10) 4_676 3_766 ?
Cu2 Cu1 Cu2 55.81(2) . 3_766 ?
O1 Cu1 H1 15.8(16) . . ?
O2 Cu1 H1 163.1(17) . . ?
O5 Cu1 H1 89.5(18) 1_656 . ?
N2 Cu1 H1 88.6(18) . . ?
O4 Cu1 H1 102.4(17) 4_676 . ?
Cu2 Cu1 H1 49.5(17) . . ?
Cu2 Cu1 H1 43.6(17) 3_766 . ?
O6 Cu2 O1 172.85(17) 1_656 3_766 ?
O6 Cu2 O1 93.13(15) 1_656 . ?
O1 Cu2 O1 81.88(16) 3_766 . ?
O6 Cu2 N3 91.64(16) 1_656 3_766 ?
O1 Cu2 N3 89.01(16) 3_766 3_766 ?
O1 Cu2 N3 140.32(16) . 3_766 ?
O6 Cu2 O3 89.93(17) 1_656 4_676 ?
O1 Cu2 O3 96.68(16) 3_766 4_676 ?
O1 Cu2 O3 112.16(15) . 4_676 ?
N3 Cu2 O3 107.21(17) 3_766 4_676 ?
O6 Cu2 Cu2 132.67(12) 1_656 3_766 ?
O1 Cu2 Cu2 42.14(11) 3_766 3_766 ?
O1 Cu2 Cu2 39.74(10) . 3_766 ?
N3 Cu2 Cu2 120.69(12) 3_766 3_766 ?
O3 Cu2 Cu2 109.32(10) 4_676 3_766 ?
O6 Cu2 Cu1 79.50(11) 1_656 . ?
O1 Cu2 Cu1 99.03(11) 3_766 . ?
O1 Cu2 Cu1 35.78(10) . . ?
N3 Cu2 Cu1 169.22(13) 3_766 . ?
O3 Cu2 Cu1 79.13(11) 4_676 . ?
Cu2 Cu2 Cu1 63.36(3) 3_766 . ?
O6 Cu2 Cu1 143.64(11) 1_656 3_766 ?
O1 Cu2 Cu1 32.90(11) 3_766 3_766 ?
O1 Cu2 Cu1 94.64(10) . 3_766 ?
N3 Cu2 Cu1 60.83(11) 3_766 3_766 ?
O3 Cu2 Cu1 119.36(12) 4_676 3_766 ?
Cu2 Cu2 Cu1 60.84(2) 3_766 3_766 ?
Cu1 Cu2 Cu1 124.19(2) . 3_766 ?
Cu1 O1 Cu2 114.01(17) . 3_766 ?
Cu1 O1 Cu2 106.14(17) . . ?
Cu2 O1 Cu2 98.13(16) 3_766 . ?
Cu1 O1 H1 107(6) . . ?
Cu2 O1 H1 111(6) 3_766 . ?
Cu2 O1 H1 120(6) . . ?
C10 O2 Cu1 132.8(6) . . ?
C8 O3 Cu2 114.1(3) . 4_475 ?
C8 O4 Cu1 116.2(4) . 4_475 ?
C9 O5 Cu1 134.4(3) . 1_454 ?
C9 O6 Cu2 124.1(3) . 1_454 ?
O12' O7 O9 39.4(12) . . ?
O8' O8 O9 101(5) . . ?
O8' O8 O9' 69(4) . . ?
O9 O8 O9' 32.9(13) . . ?
O8 O8' O9' 88(5) . . ?
O8 O8' O9 58(4) . . ?
O9' O8' O9 31.4(11) . . ?
O9' O9 O12' 93(3) . . ?
O9' O9 O12 39.3(19) . . ?
O12' O9 O12 54.9(18) . . ?
O9' O9 O8 83(3) . . ?
O12' O9 O8 175(4) . . ?
O12 O9 O8 122(3) . . ?
O9' O9 O7 154(3) . . ?
O12' O9 O7 63(2) . . ?
O12 O9 O7 118(2) . . ?
O8 O9 O7 120(2) . . ?
O9' O9 O8' 63(3) . . ?
O12' O9 O8' 154(3) . . ?
O12 O9 O8' 102(3) . . ?
O8 O9 O8' 21.6(14) . . ?
O7 O9 O8' 137.8(19) . . ?
O12 O9' O9 99(3) . . ?
O12 O9' O12' 52.8(19) . . ?
O9 O9' O12' 48(2) . . ?
O12 O9' O8' 174(4) . . ?
O9 O9' O8' 86(3) . . ?
O12' O9' O8' 132(3) . . ?
O12 O9' O8 159(3) . . ?
O9 O9' O8 64(3) . . ?
O12' O9' O8 111(3) . . ?
O8' O9' O8 23.1(13) . . ?
O12 O9' O10 65(2) . 4_475 ?
O9 O9' O10 160(3) . 4_475 ?
O12' O9' O10 118(2) . 4_475 ?
O8' O9' O10 109.3(18) . 4_475 ?
O8 O9' O10 128.6(18) . 4_475 ?
O12 O10 O9' 30.0(10) 4_676 4_676 ?
O12' O11 O12 45.6(11) . . ?
O9' O12 O12' 90(3) . . ?
O9' O12 O9 42(2) . . ?
O12' O12 O9 49.4(16) . . ?
O9' O12 O11 151(3) . . ?
O12' O12 O11 62(2) . . ?
O9 O12 O11 111(2) . . ?
O9' O12 O10 85(3) . 4_475 ?
O12' O12 O10 175(3) . 4_475 ?
O9 O12 O10 125(3) . 4_475 ?
O11 O12 O10 123.4(16) . 4_475 ?
O9 O12' O12 76(3) . . ?
O9 O12' O11 148(3) . . ?
O12 O12' O11 73(2) . . ?
O9 O12' O9' 39.7(18) . . ?
O12 O12' O9' 37.2(14) . . ?
O11 O12' O9' 109(2) . . ?
O9 O12' O7 77(3) . . ?
O12 O12' O7 153(3) . . ?
O11 O12' O7 134(2) . . ?
O9' O12' O7 116(2) . . ?
N2 N1 C1 103.9(4) . . ?
N3 N2 N1 110.3(4) . . ?
N3 N2 Cu1 120.5(3) . . ?
N1 N2 Cu1 128.3(3) . . ?
N2 N3 N4 109.7(4) . . ?
N2 N3 Cu2 116.6(3) . 3_766 ?
N4 N3 Cu2 133.7(3) . 3_766 ?
N3 N4 C1 103.9(4) . . ?
C10 N5 C13 130.8(14) . . ?
C10 N5 C12 109.9(11) . . ?
C13 N5 C12 119.0(13) . . ?
N1 C1 N4 112.2(4) . . ?
N1 C1 C2 122.6(5) . . ?
N4 C1 C2 125.2(4) . . ?
C7 C2 C3 119.9(5) . . ?
C7 C2 C1 121.5(5) . . ?
C3 C2 C1 118.6(4) . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3B 119.6 . . ?
C2 C3 H3B 119.6 . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 C8 120.8(5) . . ?
C5 C4 C8 120.4(5) . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 C9 120.6(4) . . ?
C7 C6 C9 119.7(5) . . ?
C2 C7 C6 119.7(5) . . ?
C2 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
O4 C8 O3 125.7(5) . . ?
O4 C8 C4 116.8(5) . . ?
O3 C8 C4 117.4(5) . . ?
O6 C9 O5 127.5(5) . . ?
O6 C9 C6 116.7(4) . . ?
O5 C9 C6 115.9(5) . . ?
O2 C10 N5 128.0(12) . . ?
O2 C10 C11 117.9(10) . . ?
N5 C10 C11 114.1(10) . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11D 109.5 . . ?
H11B C11 H11D 109.5 . . ?
H11C C11 H11D 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O9 O8 O8' O9' 10(3) . . . . ?
O9' O8 O8' O9 -10(3) . . . . ?
O8' O8 O9 O9' -17(6) . . . . ?
O8' O8 O9 O12 -26(6) . . . . ?
O9' O8 O9 O12 -8(2) . . . . ?
O8' O8 O9 O7 151(5) . . . . ?
O9' O8 O9 O7 168(4) . . . . ?
O9' O8 O9 O8' 17(6) . . . . ?
O12' O7 O9 O9' -24(7) . . . . ?
O12' O7 O9 O12 1.0(19) . . . . ?
O12' O7 O9 O8 -175(3) . . . . ?
O12' O7 O9 O8' -160(4) . . . . ?
O8 O8' O9 O9' 161(6) . . . . ?
O8 O8' O9 O12' -175(7) . . . . ?
O9' O8' O9 O12' 24(5) . . . . ?
O8 O8' O9 O12 158(5) . . . . ?
O9' O8' O9 O12 -3(2) . . . . ?
O9' O8' O9 O8 -161(6) . . . . ?
O8 O8' O9 O7 -39(6) . . . . ?
O9' O8' O9 O7 160(5) . . . . ?
O12' O9 O9' O12 15(4) . . . . ?
O8 O9 O9' O12 -169(3) . . . . ?
O7 O9 O9' O12 36(9) . . . . ?
O8' O9 O9' O12 -176(4) . . . . ?
O12 O9 O9' O12' -15(4) . . . . ?
O8 O9 O9' O12' 177(3) . . . . ?
O7 O9 O9' O12' 21(6) . . . . ?
O8' O9 O9' O12' 170(2) . . . . ?
O12' O9 O9' O8' -170(2) . . . . ?
O12 O9 O9' O8' 176(4) . . . . ?
O8 O9 O9' O8' 7(2) . . . . ?
O7 O9 O9' O8' -148(7) . . . . ?
O12' O9 O9' O8 -177(3) . . . . ?
O12 O9 O9' O8 169(3) . . . . ?
O7 O9 O9' O8 -155(8) . . . . ?
O8' O9 O9' O8 -7(2) . . . . ?
O12' O9 O9' O10 51(10) . . . 4_475 ?
O12 O9 O9' O10 37(8) . . . 4_475 ?
O8 O9 O9' O10 -132(9) . . . 4_475 ?
O7 O9 O9' O10 73(13) . . . 4_475 ?
O8' O9 O9' O10 -139(10) . . . 4_475 ?
O8 O8' O9' O9 -16(5) . . . . ?
O8 O8' O9' O12' -27(6) . . . . ?
O9 O8' O9' O12' -10(2) . . . . ?
O9 O8' O9' O8 16(5) . . . . ?
O8 O8' O9' O10 150(5) . . . 4_475 ?
O9 O8' O9' O10 166(4) . . . 4_475 ?
O8' O8 O9' O12 -165(10) . . . . ?
O9 O8 O9' O12 33(8) . . . . ?
O8' O8 O9' O9 162(6) . . . . ?
O8' O8 O9' O12' 159(5) . . . . ?
O9 O8 O9' O12' -3(2) . . . . ?
O9 O8 O9' O8' -162(6) . . . . ?
O8' O8 O9' O10 -38(6) . . . 4_475 ?
O9 O8 O9' O10 161(4) . . . 4_475 ?
O9 O9' O12 O12' -14(4) . . . . ?
O8 O9' O12 O12' -44(10) . . . . ?
O10 O9' O12 O12' 180(2) 4_475 . . . ?
O12' O9' O12 O9 14(4) . . . . ?
O8 O9' O12 O9 -30(8) . . . . ?
O10 O9' O12 O9 -167(3) 4_475 . . . ?
O9 O9' O12 O11 -30(7) . . . . ?
O12' O9' O12 O11 -17(5) . . . . ?
O8 O9' O12 O11 -60(13) . . . . ?
O10 O9' O12 O11 163(6) 4_475 . . . ?
O9 O9' O12 O10 167(3) . . . 4_475 ?
O12' O9' O12 O10 -180(2) . . . 4_475 ?
O8 O9' O12 O10 137(9) . . . 4_475 ?
O12' O9 O12 O9' -162(5) . . . . ?
O8 O9 O12 O9' 13(4) . . . . ?
O7 O9 O12 O9' -163(4) . . . . ?
O8' O9 O12 O9' 4(3) . . . . ?
O9' O9 O12 O12' 162(5) . . . . ?
O8 O9 O12 O12' 175(3) . . . . ?
O7 O9 O12 O12' -1(2) . . . . ?
O8' O9 O12 O12' 166(3) . . . . ?
O9' O9 O12 O11 165(4) . . . . ?
O12' O9 O12 O11 3(2) . . . . ?
O8 O9 O12 O11 178(2) . . . . ?
O7 O9 O12 O11 2(3) . . . . ?
O8' O9 O12 O11 168.5(16) . . . . ?
O9' O9 O12 O10 -16(4) . . . 4_475 ?
O12' O9 O12 O10 -178(3) . . . 4_475 ?
O8 O9 O12 O10 -3(4) . . . 4_475 ?
O7 O9 O12 O10 -179.3(17) . . . 4_475 ?
O8' O9 O12 O10 -12(3) . . . 4_475 ?
O12' O11 O12 O9' 19(5) . . . . ?
O12' O11 O12 O9 -2.3(19) . . . . ?
O12' O11 O12 O10 179(3) . . . 4_475 ?
O9' O9 O12' O12 -11(3) . . . . ?
O7 O9 O12' O12 179(2) . . . . ?
O8' O9 O12' O12 -32(6) . . . . ?
O9' O9 O12' O11 -16(6) . . . . ?
O12 O9 O12' O11 -5(4) . . . . ?
O7 O9 O12' O11 174(5) . . . . ?
O8' O9 O12' O11 -37(9) . . . . ?
O12 O9 O12' O9' 11(3) . . . . ?
O7 O9 O12' O9' -170(3) . . . . ?
O8' O9 O12' O9' -21(5) . . . . ?
O9' O9 O12' O7 170(3) . . . . ?
O12 O9 O12' O7 -179(2) . . . . ?
O8' O9 O12' O7 149(6) . . . . ?
O9' O12 O12' O9 12(3) . . . . ?
O11 O12 O12' O9 -177(2) . . . . ?
O9' O12 O12' O11 -171(3) . . . . ?
O9 O12 O12' O11 177(2) . . . . ?
O9 O12 O12' O9' -12(3) . . . . ?
O11 O12 O12' O9' 171(3) . . . . ?
O9' O12 O12' O7 14(6) . . . . ?
O9 O12 O12' O7 2(4) . . . . ?
O11 O12 O12' O7 -175(5) . . . . ?
O12 O11 O12' O9 5(4) . . . . ?
O12 O11 O12' O9' -5.9(17) . . . . ?
O12 O11 O12' O7 177(3) . . . . ?
O12 O9' O12' O9 -162(5) . . . . ?
O8' O9' O12' O9 14(3) . . . . ?
O8 O9' O12' O9 3(3) . . . . ?
O10 O9' O12' O9 -162(4) 4_475 . . . ?
O9 O9' O12' O12 162(5) . . . . ?
O8' O9' O12' O12 176(5) . . . . ?
O8 O9' O12' O12 165(4) . . . . ?
O10 O9' O12' O12 0(2) 4_475 . . . ?
O12 O9' O12' O11 9(3) . . . . ?
O9 O9' O12' O11 171(3) . . . . ?
O8' O9' O12' O11 -175(2) . . . . ?
O8 O9' O12' O11 174.2(18) . . . . ?
O10 O9' O12' O11 9(3) 4_475 . . . ?
O12 O9' O12' O7 -173(3) . . . . ?
O9 O9' O12' O7 -11(3) . . . . ?
O8' O9' O12' O7 3(4) . . . . ?
O8 O9' O12' O7 -8(3) . . . . ?
O10 O9' O12' O7 -173.2(17) 4_475 . . . ?
O9 O7 O12' O12 -2(4) . . . . ?
O9 O7 O12' O11 -176(4) . . . . ?
O9 O7 O12' O9' 7(2) . . . . ?
C1 N1 N2 N3 0.4(6) . . . . ?
C1 N1 N2 Cu1 169.4(4) . . . . ?
N1 N2 N3 N4 0.2(6) . . . . ?
Cu1 N2 N3 N4 -169.9(3) . . . . ?
N1 N2 N3 Cu2 -179.5(3) . . . 3_766 ?
Cu1 N2 N3 Cu2 10.4(5) . . . 3_766 ?
N2 N3 N4 C1 -0.6(6) . . . . ?
Cu2 N3 N4 C1 179.0(4) 3_766 . . . ?
N2 N1 C1 N4 -0.8(6) . . . . ?
N2 N1 C1 C2 178.8(5) . . . . ?
N3 N4 C1 N1 0.9(6) . . . . ?
N3 N4 C1 C2 -178.7(5) . . . . ?
N1 C1 C2 C7 175.9(5) . . . . ?
N4 C1 C2 C7 -4.6(9) . . . . ?
N1 C1 C2 C3 -5.6(9) . . . . ?
N4 C1 C2 C3 174.0(5) . . . . ?
C7 C2 C3 C4 3.3(9) . . . . ?
C1 C2 C3 C4 -175.3(5) . . . . ?
C2 C3 C4 C5 -3.3(9) . . . . ?
C2 C3 C4 C8 173.6(5) . . . . ?
C3 C4 C5 C6 0.3(9) . . . . ?
C8 C4 C5 C6 -176.6(5) . . . . ?
C4 C5 C6 C7 2.7(9) . . . . ?
C4 C5 C6 C9 -176.0(5) . . . . ?
C3 C2 C7 C6 -0.2(9) . . . . ?
C1 C2 C7 C6 178.4(5) . . . . ?
C5 C6 C7 C2 -2.8(9) . . . . ?
C9 C6 C7 C2 175.9(5) . . . . ?
Cu1 O4 C8 O3 -63.6(7) 4_475 . . . ?
Cu1 O4 C8 C4 113.7(4) 4_475 . . . ?
Cu2 O3 C8 O4 4.7(8) 4_475 . . . ?
Cu2 O3 C8 C4 -172.6(4) 4_475 . . . ?
C3 C4 C8 O4 -155.7(5) . . . . ?
C5 C4 C8 O4 21.1(8) . . . . ?
C3 C4 C8 O3 21.8(8) . . . . ?
C5 C4 C8 O3 -161.3(5) . . . . ?
Cu2 O6 C9 O5 14.4(9) 1_454 . . . ?
Cu2 O6 C9 C6 -164.9(4) 1_454 . . . ?
Cu1 O5 C9 O6 5.5(10) 1_454 . . . ?
Cu1 O5 C9 C6 -175.1(4) 1_454 . . . ?
C5 C6 C9 O6 -173.3(5) . . . . ?
C7 C6 C9 O6 8.0(8) . . . . ?
C5 C6 C9 O5 7.3(8) . . . . ?
C7 C6 C9 O5 -171.4(5) . . . . ?
Cu1 O2 C10 N5 -142.1(8) . . . . ?
Cu1 O2 C10 C11 39.6(13) . . . . ?
C13 N5 C10 O2 -178.0(12) . . . . ?
C12 N5 C10 O2 8.5(15) . . . . ?
C13 N5 C10 C11 0.3(17) . . . . ?
C12 N5 C10 C11 -173.2(11) . . . . ?

_refine_diff_density_max         0.864
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.112

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1813161'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C9 H8 Co2 N4 O7'
_chemical_formula_weight         402.05

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      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                   12.3214(8)
_cell_length_b                   14.7121(10)
_cell_length_c                   6.7818(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.908(2)
_cell_angle_gamma                90
_cell_volume                     1214.53(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6299
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.778
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12822
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.236
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2134
_reflns_number_gt                1834
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0443P)²+1.9997P] 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         2134
_refine_ls_number_parameters     214
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.76688(4) 0.45341(3) 0.69909(7) 0.01395(15) Uani 1 1 d . . . . .
Co2 Co 0.81528(4) 0.24676(3) 0.45585(7) 0.01109(15) Uani 1 1 d . . . . .
O1 O 0.71126(19) 0.58342(15) 0.6858(4) 0.0156(5) Uani 1 1 d . . . . .
O2 O 0.8677(2) 0.65996(17) 0.7033(4) 0.0224(6) Uani 1 1 d . . . . .
O3 O 0.3783(2) 0.89595(17) 0.7878(4) 0.0216(6) Uani 1 1 d . . . . .
O4 O 0.3516(2) 0.76398(17) 0.6152(4) 0.0209(6) Uani 1 1 d . . . . .
O5 O 0.9450(3) 0.4957(2) 0.7295(6) 0.0411(8) Uani 1 1 d D . . . .
H5A H 0.931(4) 0.5517(16) 0.728(9) 0.062 Uiso 1 1 d D U . . .
H5C H 1.0130(18) 0.488(3) 0.736(9) 0.062 Uiso 1 1 d D U . . .
O6 O 0.83592(19) 0.32535(15) 0.7090(3) 0.0120(5) Uani 1 1 d D . . . .
H6A H 0.9035(11) 0.336(3) 0.719(6) 0.018 Uiso 1 1 d D U . . .
O7 O 0.9976(2) 0.2501(2) 0.5074(5) 0.0250(7) Uani 1 1 d . . . . .
H7A H 1.031(4) 0.274(3) 0.451(8) 0.037 Uiso 1 1 d . U . . .
H7C H 1.038(4) 0.220(3) 0.603(8) 0.037 Uiso 1 1 d . U . . .
N1 N 0.7844(2) 1.04106(18) 0.5485(4) 0.0153(6) Uani 1 1 d . . . . .
N2 N 0.8191(2) 1.12323(19) 0.6184(4) 0.0145(6) Uani 1 1 d . . . . .
N3 N 0.8103(2) 1.12789(18) 0.8052(4) 0.0136(6) Uani 1 1 d . . . . .
N4 N 0.7702(2) 1.04971(18) 0.8656(4) 0.0154(6) Uani 1 1 d . . . . .
C1 C 0.7634(3) 0.6562(2) 0.6903(5) 0.0115(7) Uani 1 1 d . . . . .
C2 C 0.7011(3) 0.7443(2) 0.6842(5) 0.0102(7) Uani 1 1 d . . . . .
C3 C 0.5877(3) 0.7429(2) 0.6810(5) 0.0125(7) Uani 1 1 d . . . . .
H3B H 0.5498 0.6880 0.6701 0.015 Uiso 1 1 calc R U . . .
C4 C 0.5315(3) 0.8241(2) 0.6944(5) 0.0150(7) Uani 1 1 d . . . . .
C5 C 0.5888(3) 0.9060(2) 0.7039(5) 0.0166(7) Uani 1 1 d . . . . .
H5B H 0.5517 0.9602 0.7167 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7005(3) 0.9079(2) 0.6947(5) 0.0111(7) Uani 1 1 d . . . . .
C7 C 0.7571(3) 0.8263(2) 0.6876(5) 0.0116(7) Uani 1 1 d . . . . .
H7B H 0.8324 0.8268 0.6852 0.014 Uiso 1 1 calc R U . . .
C8 C 0.4104(3) 0.8276(2) 0.6994(5) 0.0164(8) Uani 1 1 d . . . . .
C9 C 0.7554(3) 0.9982(2) 0.7023(5) 0.0118(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
Co1 O3 1.992(2) 2_646 ?
Co1 O1 2.029(2) . ?
Co1 O6 2.064(2) . ?
Co1 O5 2.259(3) . ?
Co1 N4 2.269(3) 4_575 ?
Co1 N1 2.347(3) 4_576 ?
Co2 O6 2.031(2) 4_565 ?
Co2 O4 2.044(3) 3_666 ?
Co2 O6 2.053(2) . ?
Co2 N3 2.104(3) 4_575 ?
Co2 N2 2.122(3) 1_545 ?
Co2 O7 2.219(3) . ?
O1 C1 1.246(4) . ?
O2 C1 1.276(4) . ?
O3 C8 1.266(4) . ?
O3 Co1 1.993(2) 2_656 ?
O4 C8 1.264(4) . ?
O4 Co2 2.044(3) 3_666 ?
O5 H5A 0.842(19) . ?
O5 H5C 0.841(19) . ?
O6 Co2 2.031(2) 4_566 ?
O6 H6A 0.839(10) . ?
O7 H7A 0.69(5) . ?
O7 H7C 0.87(5) . ?
N1 C9 1.315(4) . ?
N1 N2 1.344(4) . ?
N1 Co1 2.347(3) 4_575 ?
N2 N3 1.290(4) . ?
N2 Co2 2.122(3) 1_565 ?
N3 N4 1.341(4) . ?
N3 Co2 2.104(3) 4_576 ?
N4 C9 1.331(4) . ?
N4 Co1 2.269(3) 4_576 ?
C1 C2 1.504(4) . ?
C2 C7 1.389(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.390(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.393(5) . ?
C4 C8 1.498(5) . ?
C5 C6 1.388(5) . ?
C5 H5B 0.9300 . ?
C6 C7 1.393(5) . ?
C6 C9 1.488(5) . ?
C7 H7B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Co1 O1 95.89(10) 2_646 . ?
O3 Co1 O6 88.83(10) 2_646 . ?
O1 Co1 O6 175.26(9) . . ?
O3 Co1 O5 168.11(11) 2_646 . ?
O1 Co1 O5 93.49(10) . . ?
O6 Co1 O5 81.89(10) . . ?
O3 Co1 N4 101.00(11) 2_646 4_575 ?
O1 Co1 N4 91.89(10) . 4_575 ?
O6 Co1 N4 86.73(9) . 4_575 ?
O5 Co1 N4 85.95(13) . 4_575 ?
O3 Co1 N1 84.98(11) 2_646 4_576 ?
O1 Co1 N1 89.41(10) . 4_576 ?
O6 Co1 N1 91.48(9) . 4_576 ?
O5 Co1 N1 87.83(12) . 4_576 ?
N4 Co1 N1 173.72(11) 4_575 4_576 ?
O6 Co2 O4 90.86(10) 4_565 3_666 ?
O6 Co2 O6 165.59(13) 4_565 . ?
O4 Co2 O6 103.33(10) 3_666 . ?
O6 Co2 N3 93.18(10) 4_565 4_575 ?
O4 Co2 N3 90.03(11) 3_666 4_575 ?
O6 Co2 N3 84.43(10) . 4_575 ?
O6 Co2 N2 89.16(10) 4_565 1_545 ?
O4 Co2 N2 89.82(11) 3_666 1_545 ?
O6 Co2 N2 93.33(10) . 1_545 ?
N3 Co2 N2 177.66(11) 4_575 1_545 ?
O6 Co2 O7 83.60(11) 4_565 . ?
O4 Co2 O7 174.45(11) 3_666 . ?
O6 Co2 O7 82.22(10) . . ?
N3 Co2 O7 90.59(11) 4_575 . ?
N2 Co2 O7 89.79(11) 1_545 . ?
C1 O1 Co1 129.7(2) . . ?
C8 O3 Co1 135.0(2) . 2_656 ?
C8 O4 Co2 130.5(2) . 3_666 ?
Co1 O5 H5A 94(3) . . ?
Co1 O5 H5C 156(3) . . ?
H5A O5 H5C 110(3) . . ?
Co2 O6 Co2 112.34(11) 4_566 . ?
Co2 O6 Co1 113.58(11) 4_566 . ?
Co2 O6 Co1 119.34(11) . . ?
Co2 O6 H6A 106(3) 4_566 . ?
Co2 O6 H6A 99(3) . . ?
Co1 O6 H6A 104(3) . . ?
Co2 O7 H7A 126(4) . . ?
Co2 O7 H7C 124(3) . . ?
H7A O7 H7C 110(5) . . ?
C9 N1 N2 105.2(3) . . ?
C9 N1 Co1 145.5(2) . 4_575 ?
N2 N1 Co1 107.4(2) . 4_575 ?
N3 N2 N1 108.9(3) . . ?
N3 N2 Co2 117.8(2) . 1_565 ?
N1 N2 Co2 127.3(2) . 1_565 ?
N2 N3 N4 110.2(3) . . ?
N2 N3 Co2 121.5(2) . 4_576 ?
N4 N3 Co2 126.0(2) . 4_576 ?
C9 N4 N3 104.1(3) . . ?
C9 N4 Co1 142.8(2) . 4_576 ?
N3 N4 Co1 112.7(2) . 4_576 ?
O1 C1 O2 123.3(3) . . ?
O1 C1 C2 118.7(3) . . ?
O2 C1 C2 117.9(3) . . ?
C7 C2 C3 120.5(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3B 120.2 . . ?
C2 C3 H3B 120.2 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 C8 122.6(3) . . ?
C5 C4 C8 118.0(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5B 119.5 . . ?
C4 C5 H5B 119.5 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 C9 117.7(3) . . ?
C7 C6 C9 122.9(3) . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 H7B 120.0 . . ?
C6 C7 H7B 120.0 . . ?
O4 C8 O3 127.1(3) . . ?
O4 C8 C4 117.9(3) . . ?
O3 C8 C4 115.1(3) . . ?
N1 C9 N4 111.6(3) . . ?
N1 C9 C6 125.3(3) . . ?
N4 C9 C6 122.7(3) . . ?

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.109

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1813163'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C21 H16 N6 O7 Zn2'
_chemical_formula_weight         595.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.6026(3)
_cell_length_b                   10.2758(4)
_cell_length_c                   15.0264(6)
_cell_angle_alpha                93.0700(10)
_cell_angle_beta                 92.0680(10)
_cell_angle_gamma                108.4260(10)
_cell_volume                     1110.38(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9073
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.62

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.218
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11870
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3856
_reflns_number_gt                3479
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0340P)²+0.6471P] 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         3856
_refine_ls_number_parameters     334
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.31579(3) 0.33182(2) 0.63064(2) 0.02248(8) Uani 1 1 d . . . . .
Zn2 Zn 0.55387(3) 0.22524(2) 0.77825(2) 0.02311(8) Uani 1 1 d . . . . .
O1 O 0.2827(2) 0.46143(15) 0.54428(10) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.3074(4) 0.5807(2) 0.67193(12) 0.0726(8) Uani 1 1 d . . . . .
O3 O 0.4104(2) 1.07856(15) 0.67311(10) 0.0316(4) Uani 1 1 d . . . . .
O4 O 0.3054(2) 1.16311(15) 0.55606(10) 0.0285(3) Uani 1 1 d . . . . .
O5 O 0.5264(2) 0.37479(15) 0.71265(11) 0.0317(4) Uani 1 1 d D . . . .
H5 H 0.599(3) 0.4546(15) 0.7229(19) 0.048 Uiso 1 1 d D U . . .
O6 O 0.2387(6) 0.2951(5) 0.3739(2) 0.1475(16) Uani 1 1 d . . . . .
O7 O -0.0229(7) 0.6181(4) 0.7518(2) 0.1129(12) Uani 1 1 d D . . . .
H7B H -0.073(8) 0.647(7) 0.709(3) 0.169 Uiso 1 1 d D U . . .
H7C H 0.071(6) 0.599(7) 0.734(4) 0.169 Uiso 1 1 d D U . . .
N1 N -0.0868(2) 0.74032(18) 0.29733(11) 0.0237(4) Uani 1 1 d . . . . .
N2 N -0.1039(3) 0.7418(2) 0.20729(12) 0.0285(4) Uani 1 1 d . . . . .
N3 N 0.0589(3) 0.7681(2) 0.17595(12) 0.0293(4) Uani 1 1 d . . . . .
N4 N 0.1867(2) 0.78484(18) 0.24459(11) 0.0247(4) Uani 1 1 d . . . . .
N5 N 0.3879(3) 0.09207(18) 0.86508(12) 0.0256(4) Uani 1 1 d . . . . .
N6 N 0.6317(3) 0.34255(19) 0.90747(12) 0.0284(4) Uani 1 1 d . . . . .
C1 C 0.2888(3) 0.5707(2) 0.58961(15) 0.0302(5) Uani 1 1 d . . . . .
C2 C 0.2666(3) 0.6889(2) 0.54145(14) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.1974(3) 0.6718(2) 0.45260(13) 0.0215(4) Uani 1 1 d . . . . .
H3A H 0.1686 0.5865 0.4213 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1719(3) 0.7825(2) 0.41159(13) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.2159(3) 0.9102(2) 0.45760(13) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.1966 0.9836 0.4297 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2890(3) 0.9290(2) 0.54550(13) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.3129(3) 0.8177(2) 0.58656(14) 0.0228(4) Uani 1 1 d . . . . .
H7A H 0.3609 0.8294 0.6453 0.027 Uiso 1 1 calc R U . . .
C8 C 0.3402(3) 1.0676(2) 0.59553(13) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.0922(3) 0.76725(19) 0.31839(13) 0.0194(4) Uani 1 1 d . . . . .
C10 C 0.7540(4) 0.4667(3) 0.92727(17) 0.0383(6) Uani 1 1 d . . . . .
H10A H 0.8223 0.5131 0.8820 0.046 Uiso 1 1 calc R U . . .
C11 C 0.7836(4) 0.5297(3) 1.01340(19) 0.0464(7) Uani 1 1 d . . . . .
H11A H 0.8700 0.6168 1.0247 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6855(4) 0.4635(3) 1.08091(18) 0.0452(7) Uani 1 1 d . . . . .
H12A H 0.7043 0.5052 1.1385 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5560(4) 0.3318(3) 1.06318(15) 0.0355(6) Uani 1 1 d . . . . .
C14 C 0.4475(4) 0.2533(3) 1.12932(16) 0.0475(7) Uani 1 1 d . . . . .
H14A H 0.4613 0.2902 1.1880 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3261(4) 0.1273(3) 1.10841(17) 0.0463(7) Uani 1 1 d . . . . .
H15A H 0.2576 0.0783 1.1528 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1769(4) -0.0642(3) 0.99302(18) 0.0431(6) Uani 1 1 d . . . . .
H16A H 0.1065 -0.1173 1.0353 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1608(4) -0.1132(3) 0.90633(18) 0.0434(6) Uani 1 1 d . . . . .
H17A H 0.0789 -0.2001 0.8888 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2681(3) -0.0321(2) 0.84362(16) 0.0343(5) Uani 1 1 d . . . . .
H18A H 0.2550 -0.0667 0.7844 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3007(4) 0.0673(3) 1.01830(16) 0.0350(5) Uani 1 1 d . . . . .
C20 C 0.4037(3) 0.1417(2) 0.95176(14) 0.0263(5) Uani 1 1 d . . . . .
C21 C 0.5345(3) 0.2760(2) 0.97429(14) 0.0270(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
Zn1 O5 1.9051(16) . ?
Zn1 O1 1.9734(14) . ?
Zn1 O4 1.9916(14) 1_545 ?
Zn1 N1 2.0392(18) 2_566 ?
Zn2 O5 1.9306(15) . ?
Zn2 N4 2.0474(18) 2_666 ?
Zn2 N5 2.0941(18) . ?
Zn2 O3 2.1306(15) 1_545 ?
Zn2 N6 2.1883(18) . ?
O1 C1 1.269(3) . ?
O2 C1 1.235(3) . ?
O3 C8 1.249(3) . ?
O3 Zn2 2.1306(15) 1_565 ?
O4 C8 1.265(3) . ?
O4 Zn1 1.9916(14) 1_565 ?
O5 H5 0.832(10) . ?
O7 H7B 0.849(10) . ?
O7 H7C 0.844(10) . ?
N1 C9 1.323(3) . ?
N1 N2 1.356(2) . ?
N1 Zn1 2.0392(18) 2_566 ?
N2 N3 1.293(3) . ?
N3 N4 1.357(2) . ?
N4 C9 1.333(3) . ?
N4 Zn2 2.0474(18) 2_666 ?
N5 C18 1.327(3) . ?
N5 C20 1.360(3) . ?
N6 C10 1.330(3) . ?
N6 C21 1.352(3) . ?
C1 C2 1.497(3) . ?
C2 C7 1.388(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C9 1.486(3) . ?
C5 C6 1.394(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.386(3) . ?
C6 C8 1.503(3) . ?
C7 H7A 0.9300 . ?
C10 C11 1.394(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.404(4) . ?
C12 H12A 0.9300 . ?
C13 C21 1.408(3) . ?
C13 C14 1.429(4) . ?
C14 C15 1.345(4) . ?
C14 H14A 0.9300 . ?
C15 C19 1.438(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.358(4) . ?
C16 C19 1.404(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.399(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.398(3) . ?
C20 C21 1.438(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
O5 Zn1 O1 122.57(7) . . ?
O5 Zn1 O4 108.06(7) . 1_545 ?
O1 Zn1 O4 104.64(6) . 1_545 ?
O5 Zn1 N1 106.83(7) . 2_566 ?
O1 Zn1 N1 111.59(7) . 2_566 ?
O4 Zn1 N1 100.98(7) 1_545 2_566 ?
O5 Zn2 N4 106.27(7) . 2_666 ?
O5 Zn2 N5 134.18(7) . . ?
N4 Zn2 N5 119.46(7) 2_666 . ?
O5 Zn2 O3 91.40(6) . 1_545 ?
N4 Zn2 O3 96.41(7) 2_666 1_545 ?
N5 Zn2 O3 86.49(7) . 1_545 ?
O5 Zn2 N6 96.16(7) . . ?
N4 Zn2 N6 95.82(7) 2_666 . ?
N5 Zn2 N6 77.49(7) . . ?
O3 Zn2 N6 163.21(7) 1_545 . ?
C1 O1 Zn1 106.42(13) . . ?
C8 O3 Zn2 142.87(14) . 1_565 ?
C8 O4 Zn1 117.04(13) . 1_565 ?
Zn1 O5 Zn2 116.33(8) . . ?
Zn1 O5 H5 122(2) . . ?
Zn2 O5 H5 121(2) . . ?
H7B O7 H7C 109.5(18) . . ?
C9 N1 N2 106.48(17) . . ?
C9 N1 Zn1 131.79(14) . 2_566 ?
N2 N1 Zn1 120.55(14) . 2_566 ?
N3 N2 N1 108.74(17) . . ?
N2 N3 N4 109.09(17) . . ?
C9 N4 N3 105.93(17) . . ?
C9 N4 Zn2 130.59(14) . 2_666 ?
N3 N4 Zn2 120.67(13) . 2_666 ?
C18 N5 C20 117.82(19) . . ?
C18 N5 Zn2 126.81(15) . . ?
C20 N5 Zn2 115.35(14) . . ?
C10 N6 C21 118.0(2) . . ?
C10 N6 Zn2 129.44(16) . . ?
C21 N6 Zn2 112.53(14) . . ?
O2 C1 O1 121.9(2) . . ?
O2 C1 C2 119.4(2) . . ?
O1 C1 C2 118.61(19) . . ?
C7 C2 C3 119.42(19) . . ?
C7 C2 C1 119.16(18) . . ?
C3 C2 C1 121.41(19) . . ?
C4 C3 C2 119.62(18) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.56(18) . . ?
C3 C4 C9 121.25(18) . . ?
C5 C4 C9 118.17(18) . . ?
C4 C5 C6 120.21(18) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 119.05(18) . . ?
C7 C6 C8 120.28(18) . . ?
C5 C6 C8 120.67(18) . . ?
C6 C7 C2 121.13(19) . . ?
C6 C7 H7A 119.4 . . ?
C2 C7 H7A 119.4 . . ?
O3 C8 O4 125.30(19) . . ?
O3 C8 C6 117.50(18) . . ?
O4 C8 C6 117.19(18) . . ?
N1 C9 N4 109.77(18) . . ?
N1 C9 C4 123.74(18) . . ?
N4 C9 C4 126.41(19) . . ?
N6 C10 C11 122.5(2) . . ?
N6 C10 H10A 118.8 . . ?
C11 C10 H10A 118.8 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C12 C13 C21 116.8(2) . . ?
C12 C13 C14 124.0(2) . . ?
C21 C13 C14 119.2(2) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C19 120.8(2) . . ?
C14 C15 H15A 119.6 . . ?
C19 C15 H15A 119.6 . . ?
C17 C16 C19 119.5(2) . . ?
C17 C16 H16A 120.3 . . ?
C19 C16 H16A 120.3 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
N5 C18 C17 122.8(2) . . ?
N5 C18 H18A 118.6 . . ?
C17 C18 H18A 118.6 . . ?
C20 C19 C16 117.5(2) . . ?
C20 C19 C15 119.3(2) . . ?
C16 C19 C15 123.1(2) . . ?
N5 C20 C19 122.9(2) . . ?
N5 C20 C21 117.31(19) . . ?
C19 C20 C21 119.8(2) . . ?
N6 C21 C13 123.3(2) . . ?
N6 C21 C20 117.25(19) . . ?
C13 C21 C20 119.5(2) . . ?

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.064

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

data_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1813162'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C19 H14 N6 O6 Zn2'
_chemical_formula_weight         553.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   13.4270(14)
_cell_length_b                   17.2924(19)
_cell_length_c                   9.1168(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.616(4)
_cell_angle_gamma                90
_cell_volume                     2017.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.431
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34491
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4642
_reflns_number_gt                3686
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0399P)²+2.5627P] 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         4642
_refine_ls_number_parameters     304
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.94397(2) 0.06641(2) 0.14303(4) 0.02246(10) Uani 1 1 d . . . . .
Zn2 Zn 0.74649(3) 0.12694(2) -0.15924(4) 0.02756(10) Uani 1 1 d . . . . .
O1 O 0.87227(16) 0.06671(12) -0.0729(2) 0.0263(4) Uani 1 1 d . . . . .
H1 H 0.872(3) 0.028(2) -0.106(4) 0.039 Uiso 1 1 d . U . . .
O2 O 1.1902(2) 0.07568(14) 0.8645(3) 0.0498(7) Uani 1 1 d . . . . .
O3 O 1.04688(18) 0.01882(12) 0.7160(2) 0.0345(5) Uani 1 1 d . . . . .
O4 O 1.24746(18) 0.36102(14) 0.7518(3) 0.0504(7) Uani 1 1 d . . . . .
O5 O 1.09457(16) 0.42022(11) 0.6829(3) 0.0306(5) Uani 1 1 d . . . . .
O6 O 0.6666(3) -0.0026(3) -0.1003(5) 0.1051(16) Uani 1 1 d . . . . .
H6B H 0.645(6) -0.050(5) -0.079(10) 0.158 Uiso 1 1 d . U . . .
N1 N 0.86511(17) 0.16000(13) 0.1904(2) 0.0205(5) Uani 1 1 d . . . . .
N2 N 0.78019(18) 0.18170(14) 0.0751(3) 0.0254(5) Uani 1 1 d . . . . .
N3 N 0.74346(19) 0.24599(14) 0.1119(3) 0.0286(5) Uani 1 1 d . . . . .
N4 N 0.80373(18) 0.26818(13) 0.2527(3) 0.0231(5) Uani 1 1 d . . . . .
N5 N 0.5866(2) 0.15392(17) -0.2273(3) 0.0352(6) Uani 1 1 d . . . . .
N6 N 0.69505(19) 0.08268(14) -0.3874(3) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.8785(2) 0.21461(15) 0.2975(3) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.9647(2) 0.21495(15) 0.4429(3) 0.0195(5) Uani 1 1 d . . . . .
C3 C 0.9962(2) 0.14675(16) 0.5247(3) 0.0220(6) Uani 1 1 d . . . . .
H3A H 0.9630 0.1004 0.4878 0.026 Uiso 1 1 calc R U . . .
C4 C 1.0778(2) 0.14822(15) 0.6618(3) 0.0219(6) Uani 1 1 d . . . . .
C5 C 1.1291(2) 0.21706(16) 0.7143(3) 0.0233(6) Uani 1 1 d . . . . .
H5A H 1.1852 0.2174 0.8041 0.028 Uiso 1 1 calc R U . . .
C6 C 1.0977(2) 0.28521(15) 0.6345(3) 0.0219(6) Uani 1 1 d . . . . .
C7 C 1.0148(2) 0.28412(15) 0.4977(3) 0.0204(5) Uani 1 1 d . . . . .
H7A H 0.9931 0.3297 0.4434 0.025 Uiso 1 1 calc R U . . .
C8 C 1.1088(2) 0.07591(16) 0.7565(3) 0.0274(6) Uani 1 1 d . . . . .
C9 C 1.1524(2) 0.36026(17) 0.6953(3) 0.0273(6) Uani 1 1 d . . . . .
C10 C 0.5325(3) 0.1827(3) -0.1395(5) 0.0682(14) Uani 1 1 d . . . . .
H10A H 0.5685 0.1976 -0.0394 0.082 Uiso 1 1 calc R U . . .
C11 C 0.4260(4) 0.1915(4) -0.1901(7) 0.0949(19) Uani 1 1 d . U . . .
H11A H 0.3904 0.2109 -0.1250 0.114 Uiso 1 1 calc R U . . .
C12 C 0.3732(3) 0.1712(4) -0.3381(7) 0.095(2) Uani 1 1 d . U . . .
H12A H 0.3012 0.1780 -0.3760 0.114 Uiso 1 1 calc R U . . .
C13 C 0.4264(3) 0.1412(3) -0.4286(5) 0.0660(13) Uani 1 1 d . . . . .
H13A H 0.3912 0.1261 -0.5288 0.079 Uiso 1 1 calc R U . . .
C14 C 0.5336(2) 0.1329(2) -0.3717(4) 0.0361(7) Uani 1 1 d . . . . .
C15 C 0.5963(2) 0.0996(2) -0.4639(4) 0.0347(7) Uani 1 1 d . . . . .
C16 C 0.5556(4) 0.0874(3) -0.6212(5) 0.0668(13) Uani 1 1 d . . . . .
H16A H 0.4862 0.0993 -0.6728 0.080 Uiso 1 1 calc R U . . .
C17 C 0.6200(4) 0.0575(3) -0.6991(5) 0.0802(16) Uani 1 1 d . . . . .
H17A H 0.5951 0.0496 -0.8048 0.096 Uiso 1 1 calc R U . . .
C18 C 0.7211(4) 0.0396(3) -0.6188(5) 0.0699(13) Uani 1 1 d . . . . .
H18A H 0.7657 0.0190 -0.6694 0.084 Uiso 1 1 calc R U . . .
C19 C 0.7560(3) 0.0522(2) -0.4623(4) 0.0439(8) Uani 1 1 d . . . . .
H19A H 0.8243 0.0389 -0.4077 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.912(2) . ?
Zn1 O3 1.935(2) 3_756 ?
Zn1 O5 1.957(2) 4_565 ?
Zn1 N1 2.050(2) . ?
Zn2 O1 1.937(2) . ?
Zn2 N5 2.099(3) . ?
Zn2 N6 2.126(3) . ?
Zn2 N4 2.213(2) 4_565 ?
Zn2 N2 2.254(2) . ?
O1 H1 0.73(4) . ?
O2 C8 1.230(4) . ?
O3 C8 1.271(4) . ?
O3 Zn1 1.935(2) 3_756 ?
O4 C9 1.224(4) . ?
O5 C9 1.280(4) . ?
O5 Zn1 1.957(2) 4_566 ?
O6 H6B 0.90(8) . ?
N1 C1 1.331(3) . ?
N1 N2 1.349(3) . ?
N2 N3 1.301(3) . ?
N3 N4 1.349(3) . ?
N4 C1 1.335(3) . ?
N4 Zn2 2.213(2) 4_566 ?
N5 C10 1.329(5) . ?
N5 C14 1.343(4) . ?
N6 C19 1.324(4) . ?
N6 C15 1.330(4) . ?
C1 C2 1.473(4) . ?
C2 C7 1.389(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(4) . ?
C4 C8 1.505(4) . ?
C5 C6 1.382(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(4) . ?
C6 C9 1.511(4) . ?
C7 H7A 0.9300 . ?
C10 C11 1.372(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.366(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.348(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.381(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.475(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.375(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(7) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(6) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O3 126.66(9) . 3_756 ?
O1 Zn1 O5 111.17(9) . 4_565 ?
O3 Zn1 O5 96.44(9) 3_756 4_565 ?
O1 Zn1 N1 94.79(9) . . ?
O3 Zn1 N1 113.22(9) 3_756 . ?
O5 Zn1 N1 115.98(9) 4_565 . ?
O1 Zn2 N5 158.08(10) . . ?
O1 Zn2 N6 100.90(9) . . ?
N5 Zn2 N6 77.90(10) . . ?
O1 Zn2 N4 103.43(9) . 4_565 ?
N5 Zn2 N4 98.45(10) . 4_565 ?
N6 Zn2 N4 89.17(9) . 4_565 ?
O1 Zn2 N2 86.59(8) . . ?
N5 Zn2 N2 94.64(9) . . ?
N6 Zn2 N2 172.38(9) . . ?
N4 Zn2 N2 90.43(9) 4_565 . ?
Zn1 O1 Zn2 121.69(11) . . ?
Zn1 O1 H1 111(3) . . ?
Zn2 O1 H1 115(3) . . ?
C8 O3 Zn1 119.60(19) . 3_756 ?
C9 O5 Zn1 132.63(19) . 4_566 ?
C1 N1 N2 105.6(2) . . ?
C1 N1 Zn1 138.69(19) . . ?
N2 N1 Zn1 115.09(17) . . ?
N3 N2 N1 109.5(2) . . ?
N3 N2 Zn2 128.36(18) . . ?
N1 N2 Zn2 120.10(17) . . ?
N2 N3 N4 108.9(2) . . ?
C1 N4 N3 105.8(2) . . ?
C1 N4 Zn2 140.23(18) . 4_566 ?
N3 N4 Zn2 113.83(16) . 4_566 ?
C10 N5 C14 117.9(3) . . ?
C10 N5 Zn2 127.0(2) . . ?
C14 N5 Zn2 114.9(2) . . ?
C19 N6 C15 119.4(3) . . ?
C19 N6 Zn2 125.4(2) . . ?
C15 N6 Zn2 114.3(2) . . ?
N1 C1 N4 110.2(2) . . ?
N1 C1 C2 123.9(2) . . ?
N4 C1 C2 125.9(2) . . ?
C7 C2 C3 120.1(2) . . ?
C7 C2 C1 119.4(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 C8 119.6(2) . . ?
C3 C4 C8 120.4(3) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 C9 120.1(2) . . ?
C7 C6 C9 120.4(2) . . ?
C2 C7 C6 120.1(2) . . ?
C2 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
O2 C8 O3 125.1(3) . . ?
O2 C8 C4 119.1(3) . . ?
O3 C8 C4 115.8(3) . . ?
O4 C9 O5 123.8(3) . . ?
O4 C9 C6 119.5(3) . . ?
O5 C9 C6 116.7(2) . . ?
N5 C10 C11 122.9(4) . . ?
N5 C10 H10A 118.6 . . ?
C11 C10 H10A 118.6 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11A 120.7 . . ?
C10 C11 H11A 120.7 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
N5 C14 C13 121.5(3) . . ?
N5 C14 C15 116.1(3) . . ?
C13 C14 C15 122.4(3) . . ?
N6 C15 C16 121.8(3) . . ?
N6 C15 C14 115.9(3) . . ?
C16 C15 C14 122.3(3) . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 H16A 120.7 . . ?
C15 C16 H16A 120.7 . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 H17A 120.5 . . ?
C16 C17 H17A 120.5 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
N6 C19 C18 121.8(4) . . ?
N6 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?

_refine_diff_density_max         0.700
_refine_diff_density_min         -0.664
_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_4_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1813164'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C14 H8 N5 O5 Zn2'
_chemical_formula_weight         457.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.9093(14)
_cell_length_b                   8.4758(14)
_cell_length_c                   11.879(2)
_cell_angle_alpha                105.314(5)
_cell_angle_beta                 105.849(6)
_cell_angle_gamma                94.385(6)
_cell_volume                     729.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8388
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.331
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.776
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13714
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.784
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3334
_reflns_number_gt                2943
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0298P)²+0.8964P] 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         3334
_refine_ls_number_parameters     238
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.30105(4) 0.61545(3) 0.21951(2) 0.01904(8) Uani 1 1 d . . . . .
Zn2 Zn -0.07191(4) 0.29966(3) 0.12567(2) 0.01895(8) Uani 1 1 d . . . . .
O1 O 0.5325(3) 0.7997(3) 0.41549(18) 0.0421(5) Uani 1 1 d . . . . .
O2 O 0.2912(3) 0.6271(3) 0.38667(17) 0.0400(5) Uani 1 1 d . . . . .
O3 O 0.7895(2) 1.2067(2) 0.84563(17) 0.0273(4) Uani 1 1 d . . . . .
O4 O 0.7914(3) 1.0986(2) 0.99558(16) 0.0326(4) Uani 1 1 d . . . . .
O5 O 0.1352(2) 0.4154(2) 0.11698(16) 0.0233(4) Uani 1 1 d . . . . .
H5 H 0.130(5) 0.395(4) 0.053(3) 0.035 Uiso 1 1 d . U . . .
N1 N 0.2473(3) 0.5397(2) 0.85663(18) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.2513(3) 0.4054(3) 0.89919(19) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.3874(3) 0.3369(2) 0.88434(18) 0.0220(4) Uani 1 1 d . . . . .
N4 N 0.4762(3) 0.4246(2) 0.83180(17) 0.0189(4) Uani 1 1 d . . . . .
N5 N -0.0392(3) 0.1934(2) 0.26532(18) 0.0215(4) Uani 1 1 d . . . . .
C1 C 0.4310(4) 0.7297(3) 0.4558(2) 0.0306(6) Uani 1 1 d . . . . .
C2 C 0.4704(4) 0.7623(3) 0.5919(2) 0.0235(5) Uani 1 1 d . . . . .
C3 C 0.5816(3) 0.9059(3) 0.6714(2) 0.0225(5) Uani 1 1 d . . . . .
H3B H 0.6300 0.9818 0.6401 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6215(3) 0.9375(3) 0.7975(2) 0.0186(4) Uani 1 1 d . . . . .
C5 C 0.5532(3) 0.8214(3) 0.8445(2) 0.0192(5) Uani 1 1 d . . . . .
H5A H 0.5800 0.8416 0.9288 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4453(3) 0.6761(3) 0.7654(2) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.4018(3) 0.6473(3) 0.6392(2) 0.0227(5) Uani 1 1 d . . . . .
H7A H 0.3267 0.5510 0.5864 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7402(3) 1.0925(3) 0.8839(2) 0.0199(5) Uani 1 1 d . . . . .
C9 C 0.3873(3) 0.5478(3) 0.81639(19) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.0440(5) 0.2752(4) 0.3817(3) 0.0455(9) Uani 1 1 d . . . . .
H10A H 0.0940 0.3856 0.4011 0.055 Uiso 1 1 calc R U . . .
C11 C 0.0600(5) 0.2047(4) 0.4757(3) 0.0474(9) Uani 1 1 d . . . . .
H11A H 0.1178 0.2684 0.5562 0.057 Uiso 1 1 calc R U . . .
C12 C -0.0085(3) 0.0415(3) 0.4511(2) 0.0229(5) Uani 1 1 d . . . . .
C13 C -0.0964(7) -0.0403(4) 0.3316(3) 0.0765(16) Uani 1 1 d . U . . .
H13A H -0.1492 -0.1503 0.3097 0.092 Uiso 1 1 calc R U . . .
C14 C -0.1081(6) 0.0383(4) 0.2420(3) 0.0667(14) Uani 1 1 d . . . . .
H14A H -0.1681 -0.0220 0.1611 0.080 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O5 1.9430(18) . ?
Zn1 O3 1.9656(17) 2_676 ?
Zn1 O2 1.9852(19) . ?
Zn1 N4 2.040(2) 2_666 ?
Zn1 O1 2.554(2) . ?
Zn1 C1 2.590(3) . ?
Zn2 O5 1.8858(17) . ?
Zn2 O4 1.9685(18) 1_444 ?
Zn2 N1 2.029(2) 2_566 ?
Zn2 N5 2.0544(19) . ?
Zn2 H5 2.21(3) . ?
O1 C1 1.230(3) . ?
O2 C1 1.278(4) . ?
O3 C8 1.252(3) . ?
O3 Zn1 1.9656(17) 2_676 ?
O4 C8 1.262(3) . ?
O4 Zn2 1.9685(18) 1_666 ?
O5 H5 0.72(3) . ?
N1 C9 1.324(3) . ?
N1 N2 1.361(3) . ?
N1 Zn2 2.029(2) 2_566 ?
N2 N3 1.293(3) . ?
N3 N4 1.356(3) . ?
N4 C9 1.328(3) . ?
N4 Zn1 2.040(2) 2_666 ?
N5 C14 1.311(4) . ?
N5 C10 1.323(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.387(4) . ?
C2 C7 1.390(3) . ?
C3 C4 1.390(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.395(3) . ?
C4 C8 1.494(3) . ?
C5 C6 1.385(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(3) . ?
C6 C9 1.477(3) . ?
C7 H7A 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.359(4) . ?
C12 C12 1.490(4) 2_556 ?
C13 C14 1.383(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Zn1 O3 105.07(8) . 2_676 ?
O5 Zn1 O2 103.15(8) . . ?
O3 Zn1 O2 116.10(9) 2_676 . ?
O5 Zn1 N4 101.86(8) . 2_666 ?
O3 Zn1 N4 105.87(8) 2_676 2_666 ?
O2 Zn1 N4 122.42(9) . 2_666 ?
O5 Zn1 O1 155.15(7) . . ?
O3 Zn1 O1 97.42(7) 2_676 . ?
O2 Zn1 O1 56.39(8) . . ?
N4 Zn1 O1 81.63(8) 2_666 . ?
O5 Zn1 C1 130.41(8) . . ?
O3 Zn1 C1 109.11(8) 2_676 . ?
O2 Zn1 C1 28.74(9) . . ?
N4 Zn1 C1 102.07(9) 2_666 . ?
O1 Zn1 C1 27.66(8) . . ?
O5 Zn2 O4 122.11(8) . 1_444 ?
O5 Zn2 N1 107.88(8) . 2_566 ?
O4 Zn2 N1 105.79(9) 1_444 2_566 ?
O5 Zn2 N5 116.47(8) . . ?
O4 Zn2 N5 95.27(8) 1_444 . ?
N1 Zn2 N5 108.04(8) 2_566 . ?
O5 Zn2 H5 18.2(9) . . ?
O4 Zn2 H5 105.1(9) 1_444 . ?
N1 Zn2 H5 110.1(9) 2_566 . ?
N5 Zn2 H5 129.2(9) . . ?
C1 O1 Zn1 77.77(16) . . ?
C1 O2 Zn1 102.92(17) . . ?
C8 O3 Zn1 141.01(17) . 2_676 ?
C8 O4 Zn2 122.60(16) . 1_666 ?
Zn2 O5 Zn1 135.17(10) . . ?
Zn2 O5 H5 107(3) . . ?
Zn1 O5 H5 114(3) . . ?
C9 N1 N2 105.76(19) . . ?
C9 N1 Zn2 130.00(16) . 2_566 ?
N2 N1 Zn2 123.89(15) . 2_566 ?
N3 N2 N1 109.21(18) . . ?
N2 N3 N4 108.63(19) . . ?
C9 N4 N3 106.26(19) . . ?
C9 N4 Zn1 124.09(15) . 2_666 ?
N3 N4 Zn1 129.64(16) . 2_666 ?
C14 N5 C10 116.4(2) . . ?
C14 N5 Zn2 120.07(18) . . ?
C10 N5 Zn2 123.48(17) . . ?
O1 C1 O2 122.9(2) . . ?
O1 C1 C2 119.9(3) . . ?
O2 C1 C2 117.2(2) . . ?
O1 C1 Zn1 74.57(15) . . ?
O2 C1 Zn1 48.34(12) . . ?
C2 C1 Zn1 165.3(2) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 120.8(2) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3B 119.7 . . ?
C4 C3 H3B 119.7 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 C8 121.0(2) . . ?
C5 C4 C8 119.3(2) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 C9 119.2(2) . . ?
C7 C6 C9 120.5(2) . . ?
C2 C7 C6 120.2(2) . . ?
C2 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
O3 C8 O4 122.6(2) . . ?
O3 C8 C4 121.0(2) . . ?
O4 C8 C4 116.4(2) . . ?
N1 C9 N4 110.1(2) . . ?
N1 C9 C6 126.7(2) . . ?
N4 C9 C6 123.1(2) . . ?
N5 C10 C11 123.2(3) . . ?
N5 C10 H10A 118.4 . . ?
C11 C10 H10A 118.4 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C13 C12 C11 115.7(2) . . ?
C13 C12 C12 121.7(3) . 2_556 ?
C11 C12 C12 122.5(3) . 2_556 ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
N5 C14 C13 123.4(3) . . ?
N5 C14 H14A 118.3 . . ?
C13 C14 H14A 118.3 . . ?

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
O4 Zn2 O5 Zn1 178.14(12) 1_444 . . . ?
N1 Zn2 O5 Zn1 55.46(16) 2_566 . . . ?
N5 Zn2 O5 Zn1 -66.16(16) . . . . ?
C9 N1 N2 N3 -0.2(3) . . . . ?
Zn2 N1 N2 N3 -174.07(15) 2_566 . . . ?
N1 N2 N3 N4 0.1(3) . . . . ?
N2 N3 N4 C9 0.1(2) . . . . ?
N2 N3 N4 Zn1 -178.95(16) . . . 2_666 ?
Zn1 O1 C1 O2 -1.7(3) . . . . ?
Zn1 O1 C1 C2 177.7(2) . . . . ?
Zn1 O2 C1 O1 2.1(3) . . . . ?
Zn1 O2 C1 C2 -177.23(19) . . . . ?
O1 C1 C2 C3 21.3(4) . . . . ?
O2 C1 C2 C3 -159.3(2) . . . . ?
Zn1 C1 C2 C3 -167.5(6) . . . . ?
O1 C1 C2 C7 -156.3(3) . . . . ?
O2 C1 C2 C7 23.0(4) . . . . ?
Zn1 C1 C2 C7 14.8(9) . . . . ?
C7 C2 C3 C4 -1.6(4) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C2 C3 C4 C8 -179.6(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C8 C4 C5 C6 -179.0(2) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C4 C5 C6 C9 174.6(2) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 177.4(2) . . . . ?
C5 C6 C7 C2 1.8(4) . . . . ?
C9 C6 C7 C2 -174.2(2) . . . . ?
Zn1 O3 C8 O4 -108.5(3) 2_676 . . . ?
Zn1 O3 C8 C4 73.9(3) 2_676 . . . ?
Zn2 O4 C8 O3 8.5(4) 1_666 . . . ?
Zn2 O4 C8 C4 -173.72(16) 1_666 . . . ?
C3 C4 C8 O3 8.6(4) . . . . ?
C5 C4 C8 O3 -172.8(2) . . . . ?
C3 C4 C8 O4 -169.1(2) . . . . ?
C5 C4 C8 O4 9.4(3) . . . . ?
N2 N1 C9 N4 0.3(3) . . . . ?
Zn2 N1 C9 N4 173.62(16) 2_566 . . . ?
N2 N1 C9 C6 -177.6(2) . . . . ?
Zn2 N1 C9 C6 -4.3(3) 2_566 . . . ?
N3 N4 C9 N1 -0.2(3) . . . . ?
Zn1 N4 C9 N1 178.89(15) 2_666 . . . ?
N3 N4 C9 C6 177.7(2) . . . . ?
Zn1 N4 C9 C6 -3.1(3) 2_666 . . . ?
C5 C6 C9 N1 85.6(3) . . . . ?
C7 C6 C9 N1 -98.4(3) . . . . ?
C5 C6 C9 N4 -92.0(3) . . . . ?
C7 C6 C9 N4 84.0(3) . . . . ?
C14 N5 C10 C11 0.1(6) . . . . ?
Zn2 N5 C10 C11 177.6(3) . . . . ?
N5 C10 C11 C12 1.3(6) . . . . ?
C10 C11 C12 C13 -2.4(6) . . . . ?
C10 C11 C12 C12 178.7(4) . . . 2_556 ?
C11 C12 C13 C14 2.1(7) . . . . ?
C12 C12 C13 C14 -178.9(4) 2_556 . . . ?
C10 N5 C14 C13 -0.4(7) . . . . ?
Zn2 N5 C14 C13 -178.0(4) . . . . ?
C12 C13 C14 N5 -0.8(8) . . . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.088

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

data_2_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1813160'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-02-22 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            'C13 H13 Mn2 N5 O6'
_chemical_formula_weight         445.16

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.9787(8)
_cell_length_b                   19.687(2)
_cell_length_c                   11.6833(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.269(4)
_cell_angle_gamma                90
_cell_volume                     1603.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.619
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7378
_exptl_absorpt_correction_T_max  0.8814
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16468
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2819
_reflns_number_gt                2471
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0441P)²+1.6548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     280
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.180
_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
Mn1 Mn 0.63995(6) 0.58892(2) 0.22811(3) 0.01435(13) Uani 1 1 d . . . . .
Mn2 Mn 0.41114(6) 0.57089(2) -0.04399(3) 0.01670(14) Uani 1 1 d . . . . .
C1 C 0.1430(4) 0.59940(13) 0.2748(2) 0.0142(6) Uani 1 1 d . . . . .
C2 C 0.1518(4) 0.62318(14) 0.3957(2) 0.0143(6) Uani 1 1 d . . . . .
C3 C 0.0966(4) 0.68995(14) 0.4168(2) 0.0162(6) Uani 1 1 d . . . . .
H3A H 0.052(4) 0.7157(16) 0.358(3) 0.019 Uiso 1 1 d . U . . .
C4 C 0.1176(4) 0.71690(14) 0.5261(2) 0.0153(6) Uani 1 1 d . . . . .
C5 C 0.1832(4) 0.67587(14) 0.6159(2) 0.0173(6) Uani 1 1 d . . . . .
H5A H 0.193(4) 0.6936(16) 0.690(3) 0.021 Uiso 1 1 d . U . . .
C6 C 0.2302(4) 0.60825(14) 0.5965(2) 0.0163(6) Uani 1 1 d . . . . .
C7 C 0.2188(4) 0.58252(14) 0.4852(2) 0.0166(6) Uani 1 1 d . . . . .
H7A H 0.254(4) 0.5410(18) 0.473(3) 0.020 Uiso 1 1 d . U . . .
C8 C 0.0782(4) 0.79148(14) 0.5469(2) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.2951(4) 0.56402(14) 0.6958(2) 0.0195(6) Uani 1 1 d . . . . .
C10 C 0.6332(5) 0.6785(3) 0.4626(4) 0.0534(12) Uani 1 1 d D U . . .
C11 C 0.5657(7) 0.7581(3) 0.4203(5) 0.0629(14) Uani 1 1 d D U . . .
H11A H 0.482(7) 0.753(3) 0.347(4) 0.076 Uiso 1 1 d . U . . .
H11B H 0.478(8) 0.782(3) 0.446(5) 0.076 Uiso 1 1 d . U . . .
H11C H 0.663(8) 0.786(3) 0.403(4) 0.076 Uiso 1 1 d . U . . .
C12 C 0.7251(7) 0.6070(3) 0.5944(7) 0.0774(18) Uani 1 1 d D . . . .
H12A H 0.811(6) 0.593(3) 0.559(5) 0.093 Uiso 1 1 d D U . . .
H12B H 0.652(7) 0.588(3) 0.632(5) 0.093 Uiso 1 1 d D U . . .
C13 C 0.6435(8) 0.7309(4) 0.6502(5) 0.0747(19) Uani 1 1 d . . . . .
H13A H 0.557(9) 0.756(3) 0.645(5) 0.090 Uiso 1 1 d . U . . .
H13B H 0.771(8) 0.743(3) 0.680(5) 0.090 Uiso 1 1 d . U . . .
H13C H 0.574(8) 0.704(3) 0.713(5) 0.090 Uiso 1 1 d . U . . .
N1 N 0.2959(3) 0.58788(12) 0.21257(19) 0.0174(5) Uani 1 1 d . U . . .
N2 N 0.2225(3) 0.57516(12) 0.1060(2) 0.0197(5) Uani 1 1 d . U . . .
N3 N 0.0353(3) 0.57774(13) 0.1048(2) 0.0235(6) Uani 1 1 d . U . . .
N4 N -0.0199(3) 0.59296(12) 0.2107(2) 0.0195(5) Uani 1 1 d . U . . .
N5 N 0.6680(6) 0.6730(2) 0.5700(4) 0.0125(9) Uani 0.5 1 d . U P . .
N5' N 0.6144(12) 0.7195(5) 0.5186(7) 0.066(2) Uani 0.5 1 d . U P . .
O1 O 0.6407(3) 0.53665(10) 0.06322(17) 0.0160(4) Uani 1 1 d . . . . .
O2 O 0.0014(3) 0.82490(10) 0.46579(18) 0.0303(5) Uani 1 1 d . . . . .
O3 O 0.1261(3) 0.81401(10) 0.64354(18) 0.0291(5) Uani 1 1 d . . . . .
O4 O 0.3093(4) 0.59237(12) 0.79207(19) 0.0430(7) Uani 1 1 d . . . . .
O5 O 0.3334(3) 0.50361(10) 0.67591(18) 0.0298(5) Uani 1 1 d . . . . .
H5B H 0.722(6) 0.543(2) 0.046(4) 0.045 Uiso 1 1 d . U . . .
O6 O 0.6428(4) 0.63983(15) 0.3851(2) 0.0480(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
Mn1 O6 2.089(2) . ?
Mn1 O5 2.143(2) 3_666 ?
Mn1 O3 2.152(2) 4_675 ?
Mn1 O1 2.184(2) . ?
Mn1 N4 2.392(2) 1_655 ?
Mn1 N1 2.401(2) . ?
Mn2 O4 2.060(2) 1_554 ?
Mn2 O1 2.105(2) . ?
Mn2 O2 2.148(2) 4_675 ?
Mn2 O1 2.158(2) 3_665 ?
Mn2 N2 2.235(2) . ?
Mn2 Mn2 3.2071(9) 3_665 ?
C1 N1 1.334(4) . ?
C1 N4 1.342(4) . ?
C1 C2 1.487(4) . ?
C2 C7 1.384(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.386(4) . ?
C3 H3A 0.90(3) . ?
C4 C5 1.387(4) . ?
C4 C8 1.515(4) . ?
C5 C6 1.392(4) . ?
C5 H5A 0.93(3) . ?
C6 C7 1.394(4) . ?
C6 C9 1.506(4) . ?
C7 H7A 0.87(3) . ?
C8 O3 1.246(3) . ?
C8 O2 1.256(3) . ?
C9 O5 1.243(4) . ?
C9 O4 1.256(4) . ?
C10 N5' 1.050(8) . ?
C10 O6 1.188(5) . ?
C10 N5 1.273(6) . ?
C10 C11 1.705(7) . ?
C11 N5' 1.408(11) . ?
C11 H11A 1.02(5) . ?
C11 H11B 0.83(5) . ?
C11 H11C 0.90(5) . ?
C12 N5 1.385(7) . ?
C12 H12A 0.79(2) . ?
C12 H12B 0.78(2) . ?
C13 N5 1.491(6) . ?
C13 N5' 1.559(10) . ?
C13 H13A 0.78(6) . ?
C13 H13B 0.98(6) . ?
C13 H13C 1.04(6) . ?
N1 N2 1.350(3) . ?
N2 N3 1.307(3) . ?
N3 N4 1.344(3) . ?
N4 Mn1 2.392(2) 1_455 ?
N5 N5' 1.149(10) . ?
O1 Mn2 2.158(2) 3_665 ?
O1 H5B 0.62(4) . ?
O2 Mn2 2.148(2) 4_576 ?
O3 Mn1 2.152(2) 4_576 ?
O4 Mn2 2.060(2) 1_556 ?
O5 Mn1 2.143(2) 3_666 ?

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
O6 Mn1 O5 87.19(10) . 3_666 ?
O6 Mn1 O3 88.61(10) . 4_675 ?
O5 Mn1 O3 175.17(8) 3_666 4_675 ?
O6 Mn1 O1 179.13(9) . . ?
O5 Mn1 O1 93.31(8) 3_666 . ?
O3 Mn1 O1 90.86(8) 4_675 . ?
O6 Mn1 N4 94.82(9) . 1_655 ?
O5 Mn1 N4 90.39(9) 3_666 1_655 ?
O3 Mn1 N4 87.60(9) 4_675 1_655 ?
O1 Mn1 N4 84.47(8) . 1_655 ?
O6 Mn1 N1 92.59(9) . . ?
O5 Mn1 N1 95.63(9) 3_666 . ?
O3 Mn1 N1 86.92(9) 4_675 . ?
O1 Mn1 N1 88.08(7) . . ?
N4 Mn1 N1 170.68(8) 1_655 . ?
O4 Mn2 O1 147.71(10) 1_554 . ?
O4 Mn2 O2 86.74(9) 1_554 4_675 ?
O1 Mn2 O2 93.41(8) . 4_675 ?
O4 Mn2 O1 93.12(9) 1_554 3_665 ?
O1 Mn2 O1 82.43(8) . 3_665 ?
O2 Mn2 O1 171.98(8) 4_675 3_665 ?
O4 Mn2 N2 121.94(11) 1_554 . ?
O1 Mn2 N2 90.19(8) . . ?
O2 Mn2 N2 95.91(9) 4_675 . ?
O1 Mn2 N2 90.98(8) 3_665 . ?
O4 Mn2 Mn2 126.26(7) 1_554 3_665 ?
O1 Mn2 Mn2 41.84(5) . 3_665 ?
O2 Mn2 Mn2 134.86(6) 4_675 3_665 ?
O1 Mn2 Mn2 40.59(6) 3_665 3_665 ?
N2 Mn2 Mn2 90.79(7) . 3_665 ?
N1 C1 N4 111.0(2) . . ?
N1 C1 C2 124.5(2) . . ?
N4 C1 C2 124.2(2) . . ?
C7 C2 C3 120.0(3) . . ?
C7 C2 C1 122.4(2) . . ?
C3 C2 C1 117.6(2) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 120(2) . . ?
C2 C3 H3A 119(2) . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C8 120.4(2) . . ?
C5 C4 C8 120.0(2) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5A 119.5(19) . . ?
C6 C5 H5A 120.1(19) . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 C9 119.6(2) . . ?
C7 C6 C9 120.8(2) . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 H7A 121(2) . . ?
C6 C7 H7A 119(2) . . ?
O3 C8 O2 126.0(3) . . ?
O3 C8 C4 116.5(2) . . ?
O2 C8 C4 117.5(2) . . ?
O5 C9 O4 125.6(3) . . ?
O5 C9 C6 118.0(3) . . ?
O4 C9 C6 116.3(3) . . ?
N5' C10 O6 168.6(8) . . ?
N5' C10 N5 58.4(6) . . ?
O6 C10 N5 133.0(5) . . ?
N5' C10 C11 55.6(6) . . ?
O6 C10 C11 113.0(4) . . ?
N5 C10 C11 113.9(4) . . ?
N5' C11 C10 37.9(4) . . ?
N5' C11 H11A 138(3) . . ?
C10 C11 H11A 108(3) . . ?
N5' C11 H11B 100(4) . . ?
C10 C11 H11B 128(4) . . ?
H11A C11 H11B 87(4) . . ?
N5' C11 H11C 111(3) . . ?
C10 C11 H11C 115(3) . . ?
H11A C11 H11C 106(4) . . ?
H11B C11 H11C 108(5) . . ?
N5 C12 H12A 115(5) . . ?
N5 C12 H12B 112(5) . . ?
H12A C12 H12B 132(7) . . ?
N5 C13 N5' 44.2(4) . . ?
N5 C13 H13A 123(5) . . ?
N5' C13 H13A 87(5) . . ?
N5 C13 H13B 107(3) . . ?
N5' C13 H13B 118(3) . . ?
H13A C13 H13B 124(6) . . ?
N5 C13 H13C 97(3) . . ?
N5' C13 H13C 125(3) . . ?
H13A C13 H13C 90(5) . . ?
H13B C13 H13C 108(4) . . ?
C1 N1 N2 104.5(2) . . ?
C1 N1 Mn1 140.95(18) . . ?
N2 N1 Mn1 114.39(17) . . ?
N3 N2 N1 110.2(2) . . ?
N3 N2 Mn2 127.78(18) . . ?
N1 N2 Mn2 121.07(18) . . ?
N2 N3 N4 108.8(2) . . ?
C1 N4 N3 105.5(2) . . ?
C1 N4 Mn1 140.99(19) . 1_455 ?
N3 N4 Mn1 113.11(17) . 1_455 ?
N5' N5 C10 51.1(5) . . ?
N5' N5 C12 160.0(6) . . ?
C10 N5 C12 109.0(5) . . ?
N5' N5 C13 71.1(6) . . ?
C10 N5 C13 122.1(5) . . ?
C12 N5 C13 128.9(6) . . ?
C10 N5' N5 70.6(7) . . ?
C10 N5' C11 86.5(7) . . ?
N5 N5' C11 156.9(8) . . ?
C10 N5' C13 135.3(10) . . ?
N5 N5' C13 64.7(6) . . ?
C11 N5' C13 138.1(8) . . ?
Mn2 O1 Mn2 97.57(8) . 3_665 ?
Mn2 O1 Mn1 110.23(9) . . ?
Mn2 O1 Mn1 123.21(9) 3_665 . ?
Mn2 O1 H5B 115(4) . . ?
Mn2 O1 H5B 108(5) 3_665 . ?
Mn1 O1 H5B 103(4) . . ?
C8 O2 Mn2 130.98(19) . 4_576 ?
C8 O3 Mn1 137.53(19) . 4_576 ?
C9 O4 Mn2 138.9(2) . 1_556 ?
C9 O5 Mn1 136.9(2) . 3_666 ?
C10 O6 Mn1 168.1(4) . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.081

