# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1031993'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N6 O4 Zn'
_chemical_formula_weight         409.73

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                   10.370(2)
_cell_length_b                   10.025(2)
_cell_length_c                   19.575(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.13(3)
_cell_angle_gamma                90
_cell_volume                     2033.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13505
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.237
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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                   ?
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       'not measured'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19300
_diffrn_reflns_av_unetI/netI     0.2227
_diffrn_reflns_av_R_equivalents  0.2140
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4650
_reflns_number_gt                2199
_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       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Some solvent molecules'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     237
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2200
_refine_ls_R_factor_gt           0.1057
_refine_ls_wR_factor_ref         0.2574
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.006

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 0.99133(9) 0.74199(9) 0.34104(5) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.9340(6) 0.6358(7) 0.4463(4) 0.056(2) Uani 1 1 d . . . . .
O2 O 0.8034(6) 0.6816(7) 0.3602(4) 0.0489(18) Uani 1 1 d . . . . .
O3 O 1.0469(5) 0.9370(6) 0.4348(3) 0.0377(16) Uani 1 1 d . . . . .
O4 O 1.1649(5) 0.7933(6) 0.3791(3) 0.0334(15) Uani 1 1 d . . . . .
N3 N 1.1682(6) 0.5517(7) 0.2712(4) 0.0333(18) Uani 1 1 d . U . . .
N1 N 1.0397(6) 0.5817(7) 0.2827(4) 0.0293(17) Uani 1 1 d . . . . .
N5 N 0.8413(7) 0.4814(7) 0.2516(4) 0.044(2) Uani 1 1 d . . . . .
H5A H 0.798245 0.543582 0.270595 0.052 Uiso 1 1 calc R U . . .
H5B H 0.801470 0.416214 0.231509 0.052 Uiso 1 1 calc R U . . .
N2 N 0.9516(6) 0.8997(7) 0.2783(4) 0.0325(18) Uani 1 1 d . . . . .
N4 N 1.1710(7) 0.4451(7) 0.2339(4) 0.039(2) Uani 1 1 d . . . . .
C6 C 0.4844(8) 0.5382(8) 0.4711(4) 0.032(2) Uani 1 1 d . . . . .
C7 C 1.5058(8) 0.9643(8) 0.4684(4) 0.030(2) Uani 1 1 d . . . . .
C19 C 0.7144(8) 0.5701(8) 0.4563(4) 0.027(2) Uani 1 1 d . . . . .
C23 C 0.5882(8) 0.5908(8) 0.4329(4) 0.032(2) Uani 1 1 d . . . . .
H23 H 0.571042 0.638253 0.392726 0.038 Uiso 1 1 calc R U . . .
C25 C 1.2748(8) 0.9387(8) 0.4595(5) 0.032(2) Uani 1 1 d . . . . .
C27 C 1.6316(8) 0.9444(9) 0.4434(4) 0.032(2) Uani 1 1 d . . . . .
H27 H 1.641262 0.901662 0.401767 0.038 Uiso 1 1 calc R U . . .
C29 C 1.3926(7) 0.9160(8) 0.4348(4) 0.029(2) Uani 1 1 d . . . . .
H29 H 1.399319 0.867432 0.394593 0.035 Uiso 1 1 calc R U . . .
C34 C 0.9725(7) 0.4860(8) 0.2532(4) 0.0215(19) Uani 1 1 d . U . . .
C36 C 1.2625(8) 1.0128(8) 0.5202(4) 0.030(2) Uani 1 1 d . . . . .
H36 H 1.180823 1.032573 0.535382 0.036 Uiso 1 1 calc R U . . .
C39 C 0.3557(8) 0.5588(9) 0.4487(5) 0.043(3) Uani 1 1 d . . . . .
H39 H 0.337410 0.608405 0.409361 0.051 Uiso 1 1 calc R U . . .
C47 C 0.8230(9) 0.6337(9) 0.4194(5) 0.035(2) Uani 1 1 d . U . . .
C54 C 1.1550(8) 0.8886(9) 0.4219(4) 0.029(2) Uani 1 1 d . . . . .
C60 C 0.7442(8) 0.4947(9) 0.5150(5) 0.035(2) Uani 1 1 d . . . . .
H60 H 0.829659 0.480832 0.529364 0.041 Uiso 1 1 calc R U . . .
N6 N 0.0287(8) 0.2163(7) 0.4313(4) 0.050(2) Uani 1 1 d . . . . .
H6A H 0.028655 0.130082 0.442163 0.060 Uiso 1 1 calc R U . . .
H6B H 0.041040 0.262427 0.469880 0.060 Uiso 1 1 calc R U . . .
C92 C 0.1382(13) 0.2430(11) 0.3859(6) 0.081(4) Uani 1 1 d . . . . .
H92A H 0.128269 0.189832 0.345264 0.122 Uiso 1 1 calc R U . . .
H92B H 0.218101 0.220664 0.409505 0.122 Uiso 1 1 calc R U . . .
H92C H 0.138722 0.335773 0.373699 0.122 Uiso 1 1 calc R U . . .
C93 C -0.1001(12) 0.2521(11) 0.3999(7) 0.080(4) Uani 1 1 d . . . . .
H93A H -0.099540 0.343812 0.385830 0.120 Uiso 1 1 calc R U . . .
H93B H -0.165386 0.239150 0.432757 0.120 Uiso 1 1 calc R U . . .
H93C H -0.118164 0.196259 0.360843 0.120 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 O4 1.990(6) . ?
Zn1 N2 2.034(7) . ?
Zn1 N1 2.045(7) . ?
Zn1 O2 2.088(6) . ?
Zn1 O1 2.414(7) . ?
Zn1 C47 2.603(9) . ?
O1 C47 1.249(11) . ?
O2 C47 1.264(11) . ?
O3 C54 1.257(9) . ?
O4 C54 1.277(9) . ?
N3 N4 1.295(9) . ?
N3 N1 1.393(9) . ?
N1 C34 1.307(9) . ?
N5 C34 1.360(9) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N2 C34 1.337(9) 2_755 ?
N2 N4 1.362(9) 2_755 ?
C6 C6 1.394(16) 3_666 ?
C6 C39 1.405(12) . ?
C6 C23 1.434(11) . ?
C7 C29 1.410(11) . ?
C7 C27 1.425(11) . ?
C7 C7 1.437(16) 3_876 ?
C19 C23 1.386(11) . ?
C19 C60 1.400(11) . ?
C19 C47 1.503(11) . ?
C23 H23 0.9300 . ?
C25 C29 1.351(11) . ?
C25 C36 1.410(11) . ?
C25 C54 1.507(11) . ?
C27 C36 1.356(10) 3_876 ?
C27 H27 0.9300 . ?
C29 H29 0.9300 . ?
C36 H36 0.9300 . ?
C39 C60 1.386(11) 3_666 ?
C39 H39 0.9300 . ?
C60 H60 0.9300 . ?
N6 C93 1.493(13) . ?
N6 C92 1.493(13) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
C92 H92A 0.9600 . ?
C92 H92B 0.9600 . ?
C92 H92C 0.9600 . ?
C93 H93A 0.9600 . ?
C93 H93B 0.9600 . ?
C93 H93C 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
O4 Zn1 N2 100.7(3) . . ?
O4 Zn1 N1 100.1(3) . . ?
N2 Zn1 N1 108.8(3) . . ?
O4 Zn1 O2 147.7(3) . . ?
N2 Zn1 O2 99.4(3) . . ?
N1 Zn1 O2 97.0(3) . . ?
O4 Zn1 O1 92.4(2) . . ?
N2 Zn1 O1 143.8(3) . . ?
N1 Zn1 O1 101.7(3) . . ?
O2 Zn1 O1 57.2(2) . . ?
O4 Zn1 C47 120.3(3) . . ?
N2 Zn1 C47 123.7(3) . . ?
N1 Zn1 C47 100.7(3) . . ?
O2 Zn1 C47 28.7(3) . . ?
O1 Zn1 C47 28.5(2) . . ?
C47 O1 Zn1 84.2(6) . . ?
C47 O2 Zn1 98.9(6) . . ?
C54 O4 Zn1 110.2(5) . . ?
N4 N3 N1 108.1(6) . . ?
C34 N1 N3 105.5(6) . . ?
C34 N1 Zn1 133.3(5) . . ?
N3 N1 Zn1 121.1(5) . . ?
C34 N5 H5A 120.0 . . ?
C34 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C34 N2 N4 105.3(6) 2_755 2_755 ?
C34 N2 Zn1 132.2(6) 2_755 . ?
N4 N2 Zn1 122.2(5) 2_755 . ?
N3 N4 N2 109.6(7) . 2_745 ?
C6 C6 C39 121.6(10) 3_666 . ?
C6 C6 C23 118.0(10) 3_666 . ?
C39 C6 C23 120.4(8) . . ?
C29 C7 C27 123.3(8) . . ?
C29 C7 C7 118.6(9) . 3_876 ?
C27 C7 C7 118.2(10) . 3_876 ?
C23 C19 C60 122.0(8) . . ?
C23 C19 C47 119.5(8) . . ?
C60 C19 C47 118.5(8) . . ?
C19 C23 C6 119.3(8) . . ?
C19 C23 H23 120.3 . . ?
C6 C23 H23 120.3 . . ?
C29 C25 C36 120.1(8) . . ?
C29 C25 C54 120.6(8) . . ?
C36 C25 C54 119.3(8) . . ?
C36 C27 C7 120.6(8) 3_876 . ?
C36 C27 H27 119.7 3_876 . ?
C7 C27 H27 119.7 . . ?
C25 C29 C7 121.5(8) . . ?
C25 C29 H29 119.2 . . ?
C7 C29 H29 119.2 . . ?
N1 C34 N2 111.4(7) . 2_745 ?
N1 C34 N5 123.5(7) . . ?
N2 C34 N5 124.9(7) 2_745 . ?
C27 C36 C25 120.8(8) 3_876 . ?
C27 C36 H36 119.6 3_876 . ?
C25 C36 H36 119.6 . . ?
C60 C39 C6 120.2(9) 3_666 . ?
C60 C39 H39 119.9 3_666 . ?
C6 C39 H39 119.9 . . ?
O1 C47 O2 119.7(9) . . ?
O1 C47 C19 120.0(9) . . ?
O2 C47 C19 120.3(9) . . ?
O1 C47 Zn1 67.3(5) . . ?
O2 C47 Zn1 52.4(4) . . ?
C19 C47 Zn1 172.5(7) . . ?
O3 C54 O4 121.0(8) . . ?
O3 C54 C25 119.9(8) . . ?
O4 C54 C25 119.0(8) . . ?
C19 C60 C39 118.9(8) . 3_666 ?
C19 C60 H60 120.6 . . ?
C39 C60 H60 120.6 3_666 . ?
C93 N6 C92 113.6(9) . . ?
C93 N6 H6A 108.9 . . ?
C92 N6 H6A 108.9 . . ?
C93 N6 H6B 108.9 . . ?
C92 N6 H6B 108.9 . . ?
H6A N6 H6B 107.7 . . ?
N6 C92 H92A 109.5 . . ?
N6 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
N6 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
N6 C93 H93A 109.5 . . ?
N6 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
N6 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 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
N4 N3 N1 C34 2.5(9) . . . . ?
N4 N3 N1 Zn1 179.0(5) . . . . ?
N1 N3 N4 N2 -1.9(9) . . . 2_745 ?
C60 C19 C23 C6 2.5(13) . . . . ?
C47 C19 C23 C6 -175.4(7) . . . . ?
C6 C6 C23 C19 -3.3(15) 3_666 . . . ?
C39 C6 C23 C19 179.5(8) . . . . ?
C29 C7 C27 C36 -176.6(8) . . . 3_876 ?
C7 C7 C27 C36 2.6(15) 3_876 . . 3_876 ?
C36 C25 C29 C7 0.4(13) . . . . ?
C54 C25 C29 C7 178.7(8) . . . . ?
C27 C7 C29 C25 -179.0(8) . . . . ?
C7 C7 C29 C25 1.9(15) 3_876 . . . ?
N3 N1 C34 N2 -2.2(9) . . . 2_745 ?
Zn1 N1 C34 N2 -178.0(6) . . . 2_745 ?
N3 N1 C34 N5 -178.2(7) . . . . ?
Zn1 N1 C34 N5 6.0(13) . . . . ?
C29 C25 C36 C27 -3.9(14) . . . 3_876 ?
C54 C25 C36 C27 177.8(8) . . . 3_876 ?
C6 C6 C39 C60 1.5(17) 3_666 . . 3_666 ?
C23 C6 C39 C60 178.6(8) . . . 3_666 ?
Zn1 O1 C47 O2 -0.2(8) . . . . ?
Zn1 O1 C47 C19 177.7(7) . . . . ?
Zn1 O2 C47 O1 0.2(9) . . . . ?
Zn1 O2 C47 C19 -177.7(6) . . . . ?
C23 C19 C47 O1 167.3(8) . . . . ?
C60 C19 C47 O1 -10.7(12) . . . . ?
C23 C19 C47 O2 -14.8(12) . . . . ?
C60 C19 C47 O2 167.2(8) . . . . ?
Zn1 O4 C54 O3 -0.1(10) . . . . ?
Zn1 O4 C54 C25 177.0(6) . . . . ?
C29 C25 C54 O3 -162.1(8) . . . . ?
C36 C25 C54 O3 16.2(13) . . . . ?
C29 C25 C54 O4 20.8(13) . . . . ?
C36 C25 C54 O4 -160.9(8) . . . . ?
C23 C19 C60 C39 -1.1(13) . . . 3_666 ?
C47 C19 C60 C39 176.8(8) . . . 3_666 ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.128


# SQUEEZE RESULTS (Version =  21116)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.010 0.250 237 83 ' '
2 0.500 -0.015 0.750 237 83 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
