# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_18042306
_database_code_depnum_ccdc_archive 'CCDC 1872616'
_audit_update_record             
;
2018-10-11 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H7 N7 O6 Zn2'
_chemical_formula_sum            'C6 H7 N7 O6 Zn2'
_chemical_formula_weight         403.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_H-M_alt        'P n n m'
_space_group_name_Hall           '-P 2 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5016(3)
_cell_length_b                   17.0121(4)
_cell_length_c                   14.7070(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2877.68(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8940
_cell_measurement_theta_min      3.9680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6406
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.641
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  20.00   1.00    1.00    --    0.00  57.00-180.00   42
  2  ω    -16.00  20.00   1.00    1.00    --    0.00  57.00 -60.00   36
  3  ω     29.00  54.00   1.00    1.00    --    0.00  57.00 -60.00   25
  4  ω     22.00 125.00   1.00    1.00    --   54.00  77.00 -60.00  103
  5  ω     43.00 108.00   1.00    1.00    --   54.00  57.00-150.00   65
  6  ω    -15.00  18.00   1.00    1.00    --   54.00 -77.00  60.00   33
  7  ω    100.00 177.00   1.00    2.73    --  108.00  50.00-120.00   77
  8  ω     42.00 126.00   1.00    2.73    --  108.00 -63.00 150.00   84
  9  ω     35.00 111.00   1.00    2.73    --  108.00-111.00-180.00   76
 10  ω     46.00  82.00   1.00    2.73    --  108.00-111.00 -30.00   36
 11  ω     48.00  73.00   1.00    2.73    --  108.00 -37.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0439568000
_diffrn_orient_matrix_UB_12      0.0690513000
_diffrn_orient_matrix_UB_13      -0.0584683000
_diffrn_orient_matrix_UB_21      0.0416133000
_diffrn_orient_matrix_UB_22      -0.0426246000
_diffrn_orient_matrix_UB_23      -0.0864782000
_diffrn_orient_matrix_UB_31      -0.1194536000
_diffrn_orient_matrix_UB_32      -0.0402582000
_diffrn_orient_matrix_UB_33      -0.0085685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2329
_reflns_number_total             2679
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+5.1154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H5C(0.5) H5D(0.5) H8A(0.5) H8B(0.5)
3.a Rotating group:
 O5(H5A,H5B), O6(H6A,H6B), N5(H5C,H5D), N8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.02498(4) 0.10197(2) 0.21540(3) 0.01765(15) Uani 1 1 d . . . . .
Zn2 Zn -0.26953(4) 0.19340(2) 0.28445(3) 0.01864(15) Uani 1 1 d . . . . .
O1 O -0.2784(3) 0.07428(15) 0.2742(2) 0.0383(8) Uani 1 1 d . . . . .
O2 O -0.1150(2) 0.02184(14) 0.21773(18) 0.0247(5) Uani 1 1 d . . . . .
O3 O -0.5538(2) -0.21602(15) 0.30600(18) 0.0255(5) Uani 1 1 d . . . . .
O4 O -0.4228(2) -0.30150(13) 0.25363(18) 0.0214(5) Uani 1 1 d . . . . .
O5 O -0.3012(3) 0.1916(2) 0.1377(2) 0.0452(8) Uani 1 1 d . . . . .
H5A H -0.322622 0.237758 0.119378 0.068 Uiso 1 1 d GR . . . .
H5B H -0.360529 0.162135 0.124891 0.068 Uiso 1 1 d GR . . . .
O6 O 0.0304(3) 0.08103(17) 0.3630(2) 0.0356(7) Uani 1 1 d . . . . .
H6A H 0.086463 0.108087 0.387535 0.053 Uiso 1 1 d GR . . . .
H6B H 0.049714 0.032549 0.374636 0.053 Uiso 1 1 d GR . . . .
N1 N -0.2014(3) -0.12258(17) 0.2238(2) 0.0197(6) Uani 1 1 d . . . . .
N2 N -0.2646(2) -0.18824(16) 0.2300(2) 0.0196(6) Uani 1 1 d . . . . .
N3 N -0.2383(3) 0.18625(19) 0.4252(2) 0.0251(7) Uani 1 1 d . . . . .
N4 N -0.1338(3) 0.1686(4) 0.4552(3) 0.0665(15) Uani 1 1 d . . . . .
N5 N -0.4159(6) 0.2135(8) 0.500000 0.132(6) Uani 1 2 d S T P . .
H5C H -0.452305 0.179831 0.466447 0.158 Uiso 0.5 1 d GR . . . .
H5D H -0.443396 0.211087 0.554680 0.158 Uiso 0.5 1 d GR . . . .
N6 N -0.0001(3) 0.1097(2) 0.0746(2) 0.0260(7) Uani 1 1 d . . . . .
N7 N -0.1021(3) 0.1393(2) 0.0440(2) 0.0324(8) Uani 1 1 d . . . . .
N8 N 0.1682(5) 0.0614(5) 0.000000 0.075(3) Uani 1 2 d S T P . .
H8A H 0.167778 0.019753 0.033340 0.090 Uiso 0.5 1 d GR . . . .
H8B H 0.187698 0.048933 -0.054690 0.090 Uiso 0.5 1 d GR . . . .
C1 C -0.2186(3) 0.0185(2) 0.2463(3) 0.0218(7) Uani 1 1 d . . . . .
C2 C -0.2706(3) -0.0613(2) 0.2462(3) 0.0227(8) Uani 1 1 d . . . . .
C3 C -0.3728(3) -0.1686(2) 0.2566(3) 0.0216(7) Uani 1 1 d . . . . .
C4 C -0.4574(3) -0.2321(2) 0.2729(2) 0.0185(7) Uani 1 1 d . . . . .
C5 C -0.3808(3) -0.0877(2) 0.2675(3) 0.0281(9) Uani 1 1 d . . . . .
H5 H -0.445177 -0.058258 0.285005 0.034 Uiso 1 1 calc R . . . .
C6 C 0.0592(5) 0.0927(4) 0.000000 0.0342(13) Uani 1 2 d S T P . .
C7 C -0.3026(6) 0.1961(4) 0.500000 0.0358(14) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.347(2) 2 ?
Zn1 O2 2.110(2) . ?
Zn1 O4 2.070(2) 4_455 ?
Zn1 O6 2.200(3) . ?
Zn1 N1 2.063(3) 2 ?
Zn1 N6 2.095(3) . ?
Zn2 O1 2.035(3) . ?
Zn2 O3 2.092(2) 2_455 ?
Zn2 O4 2.283(2) 4_455 ?
Zn2 O5 2.189(3) . ?
Zn2 N2 2.062(3) 4_455 ?
Zn2 N3 2.104(3) . ?
O1 C1 1.242(5) . ?
O2 C1 1.264(4) . ?
O3 C4 1.242(4) . ?
O4 C4 1.278(4) . ?
O5 H5A 0.8661 . ?
O5 H5B 0.8673 . ?
O6 H6A 0.8712 . ?
O6 H6B 0.8714 . ?
N1 N2 1.335(4) . ?
N1 C2 1.351(4) . ?
N2 C3 1.347(5) . ?
N3 N4 1.315(5) . ?
N3 C7 1.336(5) . ?
N4 N4 1.318(8) 6_556 ?
N5 H5C 0.8644 . ?
N5 H5C 0.86(14) 6_556 ?
N5 H5D 0.8650 . ?
N5 H5D 0.87(4) 6_556 ?
N5 C7 1.337(9) . ?
N6 N7 1.353(4) . ?
N6 C6 1.325(4) . ?
N7 N7 1.295(6) 6 ?
N8 H8A 0.8617 . ?
N8 H8A 0.86(8) 6 ?
N8 H8B 0.8616 . ?
N8 H8B 0.86(2) 6 ?
N8 C6 1.361(8) . ?
C1 C2 1.484(5) . ?
C2 C5 1.381(5) . ?
C3 C4 1.474(5) . ?
C3 C5 1.388(5) . ?
C5 H5 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
O2 Zn1 O2 75.93(10) . 2 ?
O2 Zn1 O6 84.31(11) . . ?
O4 Zn1 O2 163.55(10) 4_455 2 ?
O4 Zn1 O2 94.33(10) 4_455 . ?
O4 Zn1 O6 85.84(11) 4_455 . ?
O4 Zn1 N6 95.11(11) 4_455 . ?
O6 Zn1 O2 80.09(10) . 2 ?
N1 Zn1 O2 149.26(11) 2 . ?
N1 Zn1 O2 73.59(10) 2 2 ?
N1 Zn1 O4 114.23(11) 2 4_455 ?
N1 Zn1 O6 86.59(11) 2 . ?
N1 Zn1 N6 100.62(12) 2 . ?
N6 Zn1 O2 87.23(12) . . ?
N6 Zn1 O2 97.58(11) . 2 ?
N6 Zn1 O6 171.53(12) . . ?
O1 Zn2 O3 98.39(11) . 2_455 ?
O1 Zn2 O4 93.91(10) . 4_455 ?
O1 Zn2 O5 84.53(13) . . ?
O1 Zn2 N2 166.99(12) . 4_455 ?
O1 Zn2 N3 91.36(13) . . ?
O3 Zn2 O4 166.16(10) 2_455 4_455 ?
O3 Zn2 O5 89.46(11) 2_455 . ?
O3 Zn2 N3 91.56(11) 2_455 . ?
O5 Zn2 O4 85.40(11) . 4_455 ?
N2 Zn2 O3 91.19(11) 4_455 2_455 ?
N2 Zn2 O4 75.72(10) 4_455 4_455 ?
N2 Zn2 O5 86.79(13) 4_455 . ?
N2 Zn2 N3 97.18(12) 4_455 . ?
N3 Zn2 O4 94.49(11) . 4_455 ?
N3 Zn2 O5 175.87(13) . . ?
C1 O1 Zn2 139.3(2) . . ?
Zn1 O2 Zn1 104.04(10) . 2 ?
C1 O2 Zn1 112.3(2) . 2 ?
C1 O2 Zn1 138.9(2) . . ?
C4 O3 Zn2 148.1(3) . 2_455 ?
Zn1 O4 Zn2 125.02(11) 4_445 4_445 ?
C4 O4 Zn1 120.5(2) . 4_445 ?
C4 O4 Zn2 113.1(2) . 4_445 ?
Zn2 O5 H5A 109.9 . . ?
Zn2 O5 H5B 110.6 . . ?
H5A O5 H5B 103.4 . . ?
Zn1 O6 H6A 110.2 . . ?
Zn1 O6 H6B 110.8 . . ?
H6A O6 H6B 103.2 . . ?
N2 N1 Zn1 132.9(2) . 2 ?
N2 N1 C2 107.9(3) . . ?
C2 N1 Zn1 117.6(2) . 2 ?
N1 N2 Zn2 134.9(2) . 4_445 ?
N1 N2 C3 108.3(3) . . ?
C3 N2 Zn2 116.6(2) . 4_445 ?
N4 N3 Zn2 119.9(3) . . ?
N4 N3 C7 104.9(3) . . ?
C7 N3 Zn2 135.1(3) . . ?
N3 N4 N4 109.6(2) . 6_556 ?
H5C N5 H5C 69.6 . 6_556 ?
H5C N5 H5D 108.8 6_556 6_556 ?
H5C N5 H5D 42.3 . 6_556 ?
H5C N5 H5D 108.8 . . ?
H5D N5 H5C 42.3 . 6_556 ?
H5D N5 H5D 136.8 . 6_556 ?
C7 N5 H5C 109(3) . 6_556 ?
C7 N5 H5C 108.9 . . ?
C7 N5 H5D 110.2 . . ?
C7 N5 H5D 110.2(10) . 6_556 ?
N7 N6 Zn1 118.1(2) . . ?
C6 N6 Zn1 137.2(3) . . ?
C6 N6 N7 104.7(3) . . ?
N7 N7 N6 109.41(19) 6 . ?
H8A N8 H8A 69.4 . 6 ?
H8A N8 H8B 109.3 6 6 ?
H8A N8 H8B 42.9 . 6 ?
H8A N8 H8B 109.3 . . ?
H8B N8 H8A 42.9 . 6 ?
H8B N8 H8B 138.0 . 6 ?
C6 N8 H8A 108.4(19) . 6 ?
C6 N8 H8A 108.4 . . ?
C6 N8 H8B 109.6 . . ?
C6 N8 H8B 109.6(5) . 6 ?
O1 C1 O2 126.6(3) . . ?
O1 C1 C2 118.5(3) . . ?
O2 C1 C2 114.9(3) . . ?
N1 C2 C1 117.9(3) . . ?
N1 C2 C5 110.2(3) . . ?
C5 C2 C1 131.8(3) . . ?
N2 C3 C4 118.3(3) . . ?
N2 C3 C5 110.0(3) . . ?
C5 C3 C4 131.6(3) . . ?
O3 C4 O4 124.7(3) . . ?
O3 C4 C3 119.4(3) . . ?
O4 C4 C3 115.8(3) . . ?
C2 C5 C3 103.6(3) . . ?
C2 C5 H5 128.2 . . ?
C3 C5 H5 128.2 . . ?
N6 C6 N6 111.9(5) 6 . ?
N6 C6 N8 124.1(2) 6 . ?
N6 C6 N8 124.1(2) . . ?
N3 C7 N3 110.9(5) . 6_556 ?
N3 C7 N5 124.6(3) . . ?
N3 C7 N5 124.6(3) 6_556 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6B O6 0.87 2.15 2.844(6) 136.6 2 yes
N5 H5D O3 0.87 2.05 2.875(3) 158.8 5_456 yes

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.383 0.117 0.500 404.7 88.1 ?
2 -0.687 -0.187 0.000 404.7 88.1 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.830
