# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1414115'
_audit_update_record             
;
2015-07-21 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_audit_creation_date             2015-07-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.07.16 svn.r3196 for OlexSys, GUI svn.r5065)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 N3 O10 Zn2'
_chemical_formula_sum            'C24 H13 N3 O10 Zn2'
_chemical_formula_weight         634.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONZn
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      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'-x, -y, -z'
'-x+y, -x, -z-1/2'
'y, -x+y, -z'
'x, y, -z-1/2'
'x-y, x, -z'
'-y, x-y, -z-1/2'

_cell_length_a                   16.7612(16)
_cell_length_b                   16.7612(16)
_cell_length_c                   6.8980(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1678.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5905
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      74.5210
_cell_measurement_theta_min      5.2350
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    2.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         5.278
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1688
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   38.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   38.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  3 omega  -62.00   37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   19.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6040  -99.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega   64.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6040 -122.0000 -117.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   28.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6040 -125.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -30.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   95.00  135.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -77.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -45.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega  114.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324   15.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324 -125.0000  -30.0000 76

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -45.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324   15.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   28.00   54.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   47.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   51.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   25.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -94.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 18 omega   71.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -94.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -94.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
 20 omega   82.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324   45.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
 21 omega   96.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324   30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  153.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324   30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   32.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3324  -30.0000  -30.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0984929000
_diffrn_orient_matrix_UB_12      0.0237243000
_diffrn_orient_matrix_UB_13      0.0553124000
_diffrn_orient_matrix_UB_21      -0.0343614000
_diffrn_orient_matrix_UB_22      -0.1026994000
_diffrn_orient_matrix_UB_23      0.0368924000
_diffrn_orient_matrix_UB_31      0.0197006000
_diffrn_orient_matrix_UB_32      -0.0116611000
_diffrn_orient_matrix_UB_33      -0.2134310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   '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                983
_reflns_number_total             1091
_reflns_odcompleteness_completeness 99.91
_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.
 
 _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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    ?
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0711
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0984P)²+4.4893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. Restrained distances
 O3-Zn1
 1.95 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.001
4. Others
 Fixed Sof: O3(0.16667) H3A(0.16667)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6667 0.3333 0.00190(14) 0.0428(5) Uani 1 3 d DS T P . .
O2 O 0.1270(3) -0.0461(3) 0.2500 0.0443(11) Uani 1 2 d S T P . .
C6 C 0.0642(4) -0.0199(4) 0.2500 0.0375(13) Uani 1 2 d S T P . .
N1 N 0.0909(3) 0.0689(3) 0.2500 0.0371(11) Uani 1 2 d S T P . .
C5 C 0.2216(4) 0.0217(4) 0.2500 0.0418(14) Uani 1 2 d S T P . .
C2 C 0.4062(4) 0.1494(5) 0.2500 0.0533(18) Uani 1 2 d S T P . .
C4 C 0.2661(3) 0.0522(4) 0.4243(9) 0.0594(14) Uani 1 1 d . . . . .
H4 H 0.2338 0.0296 0.5431 0.071 Uiso 1 1 calc R . . . .
C3 C 0.3585(4) 0.1162(4) 0.4233(10) 0.0655(15) Uani 1 1 d . . . . .
H3 H 0.3902 0.1382 0.5428 0.079 Uiso 1 1 calc R . . . .
O1 O 0.5445(3) 0.2454(3) 0.0867(9) 0.0911(16) Uani 1 1 d . . . . .
C1 C 0.5053(6) 0.2183(6) 0.2500 0.073(3) Uani 1 2 d S T P . .
O3 O 0.6160(11) 0.2788(9) -0.2500 0.103(7) Uani 0.3333 2 d DS TU P . .
H3A H 0.5616 0.2201 -0.2500 0.123 Uiso 0.3333 2 calc RS 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 O1 1.921(4) 3_655 ?
Zn1 O1 1.921(4) 5_665 ?
Zn1 O1 1.921(4) . ?
Zn1 O3 1.9493(11) 3_655 ?
Zn1 O3 1.9493(11) . ?
Zn1 O3 1.9493(11) 8_665 ?
O2 C6 1.327(7) . ?
O2 C5 1.416(7) . ?
C6 N1 1.336(7) 8_556 ?
C6 N1 1.323(7) . ?
N1 C6 1.336(7) 3 ?
C5 C4 1.372(6) 10_556 ?
C5 C4 1.372(6) . ?
C2 C3 1.390(7) 10_556 ?
C2 C3 1.390(7) . ?
C2 C1 1.476(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.373(7) . ?
C3 H3 0.9500 . ?
O1 C1 1.268(6) . ?
C1 O1 1.268(6) 10_556 ?
O3 Zn1 1.9493(11) 8_665 ?
O3 O3 1.530(5) 3_655 ?
O3 O3 1.530(5) 8_665 ?
O3 H3A 0.9500 . ?

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 O1 111.15(17) 3_655 5_665 ?
O1 Zn1 O1 111.15(17) 3_655 . ?
O1 Zn1 O1 111.16(17) 5_665 . ?
O1 Zn1 O3 82.2(3) 3_655 3_655 ?
O1 Zn1 O3 126.8(7) . 3_655 ?
O1 Zn1 O3 110.5(8) 5_665 3_655 ?
O1 Zn1 O3 110.5(8) 3_655 . ?
O1 Zn1 O3 126.8(7) 5_665 . ?
O1 Zn1 O3 110.5(8) . 8_665 ?
O1 Zn1 O3 126.8(7) 3_655 8_665 ?
O1 Zn1 O3 82.2(3) 5_665 8_665 ?
O1 Zn1 O3 82.2(3) . . ?
O3 Zn1 O3 46.22(14) 3_655 8_665 ?
O3 Zn1 O3 46.22(14) 3_655 . ?
O3 Zn1 O3 46.22(14) . 8_665 ?
C6 O2 C5 119.2(4) . . ?
O2 C6 N1 112.9(5) . 8_556 ?
N1 C6 O2 119.7(5) . . ?
N1 C6 N1 127.5(5) . 8_556 ?
C6 N1 C6 112.5(5) . 3 ?
C4 C5 O2 118.8(3) 10_556 . ?
C4 C5 O2 118.8(3) . . ?
C4 C5 C4 122.4(6) 10_556 . ?
C3 C2 C3 118.6(6) 10_556 . ?
C3 C2 C1 120.7(3) 10_556 . ?
C3 C2 C1 120.7(3) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.5(6) . . ?
C3 C4 H4 120.8 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(6) . . ?
C4 C3 H3 119.5 . . ?
C1 O1 Zn1 135.0(5) . . ?
O1 C1 C2 117.3(4) 10_556 . ?
O1 C1 C2 117.3(4) . . ?
O1 C1 O1 125.4(8) . 10_556 ?
Zn1 O3 Zn1 126.10(17) 8_665 . ?
Zn1 O3 H3A 117.0 . . ?
Zn1 O3 H3A 117.0 8_665 . ?
O3 O3 Zn1 66.89(7) 3_655 8_665 ?
O3 O3 Zn1 66.89(7) 8_665 8_665 ?
O3 O3 Zn1 66.89(7) 8_665 . ?
O3 O3 Zn1 66.89(7) 3_655 . ?
O3 O3 O3 59.998(1) 8_665 3_655 ?
O3 O3 H3A 150.0 8_665 . ?
O3 O3 H3A 150.0 3_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 C2 177.8(5) . . . . ?
Zn1 O1 C1 O1 -2.3(15) . . . 10_556 ?
O2 C6 N1 C6 180.0 . . . 3 ?
O2 C5 C4 C3 178.3(5) . . . . ?
C6 O2 C5 C4 -91.1(5) . . . 10_556 ?
C6 O2 C5 C4 91.1(5) . . . . ?
N1 C6 N1 C6 0.0 8_556 . . 3 ?
C5 O2 C6 N1 180.0 . . . 8_556 ?
C5 O2 C6 N1 0.0 . . . . ?
C5 C4 C3 C2 -0.2(9) . . . . ?
C4 C5 C4 C3 0.6(11) 10_556 . . . ?
C3 C2 C3 C4 -0.2(11) 10_556 . . . ?
C3 C2 C1 O1 179.9(7) . . . . ?
C3 C2 C1 O1 0.0(11) . . . 10_556 ?
C3 C2 C1 O1 0.0(11) 10_556 . . . ?
C3 C2 C1 O1 -179.9(7) 10_556 . . 10_556 ?
C1 C2 C3 C4 179.9(6) . . . . ?

_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 0.000 0.500 -0.442 215.9 39.6 ?
2 0.500 0.000 -0.463 215.9 39.6 ?
3 0.500 0.500 -0.111 215.9 39.6 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
