# 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_1_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1833939'
_audit_update_record             
;
2018-03-31 deposited with the CCDC.
2018-05-11 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            'C10 H6 N20 O2 Zn3'
_chemical_formula_weight         634.46

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      tetragonal
_space_group_IT_number           135
_space_group_name_H-M_alt        'P 42/m b c'
_space_group_name_Hall           '-P 4c 2ab'

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

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

_cell_length_a                   14.3715(11)
_cell_length_b                   14.3715(11)
_cell_length_c                   19.721(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4073.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3146
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.93

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.566
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24219
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         25.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1906
_reflns_number_gt                1482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+6.5571P] 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         1906
_refine_ls_number_parameters     169
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3170(3) 0.2897(3) 0.4038(2) 0.0432(11) Uani 1 1 d . . . . .
H1 H 0.3397 0.2484 0.4361 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2960(3) 0.3598(2) 0.3089(2) 0.0304(8) Uani 1 1 d . . . . .
C3 C 0.2389(3) 0.3989(3) 0.3563(2) 0.0309(8) Uani 1 1 d . . . . .
C4 C 0.3138(3) 0.3743(2) 0.23759(19) 0.0299(8) Uani 1 1 d . . . . .
C5 C 0.1734(2) 0.4757(2) 0.35621(19) 0.0279(8) Uani 1 1 d . . . . .
N1 N 0.2531(2) 0.3549(2) 0.41765(17) 0.0400(8) Uani 1 1 d . . . . .
N2 N 0.3452(2) 0.2896(2) 0.33910(17) 0.0363(8) Uani 1 1 d . . . . .
N3 N 0.3730(3) 0.3195(2) 0.20606(17) 0.0441(9) Uani 1 1 d . . . . .
N4 N 0.3734(3) 0.3487(3) 0.14080(19) 0.0599(12) Uani 1 1 d . . . . .
N5 N 0.3173(3) 0.4193(3) 0.13386(17) 0.0507(10) Uani 1 1 d . . . . .
N6 N 0.2779(2) 0.4375(2) 0.19529(16) 0.0337(8) Uani 1 1 d . . . . .
N7 N 0.1474(2) 0.5302(2) 0.30578(15) 0.0275(7) Uani 1 1 d . . . . .
N8 N 0.0890(2) 0.5928(2) 0.33487(16) 0.0300(7) Uani 1 1 d . . . . .
N9 N 0.0802(2) 0.5755(2) 0.39968(17) 0.0349(8) Uani 1 1 d . . . . .
N10 N 0.1328(2) 0.5010(2) 0.41458(15) 0.0318(7) Uani 1 1 d . . . . .
O1 O 0.0661(4) 0.3251(4) 0.5000 0.0615(13) Uani 1 2 d DS T P . .
H1W H 0.054(4) 0.293(4) 0.463(2) 0.092 Uiso 1 1 d D U . . .
O2 O 0.3009(5) 0.5308(5) 0.5000 0.096(2) Uani 1 2 d DS T P . .
H2W H 0.326(5) 0.550(5) 0.537(2) 0.144 Uiso 1 1 d D U . . .
Zn1 Zn 0.21814(3) 0.55904(3) 0.21569(2) 0.02803(16) Uani 1 1 d . . . . .
Zn2 Zn 0.18293(5) 0.41230(5) 0.5000 0.0413(2) 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
C1 N2 1.339(5) . ?
C1 N1 1.340(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(5) . ?
C2 N2 1.368(5) . ?
C2 C4 1.444(5) . ?
C3 N1 1.381(5) . ?
C3 C5 1.451(5) . ?
C4 N3 1.315(5) . ?
C4 N6 1.337(5) . ?
C5 N7 1.320(5) . ?
C5 N10 1.341(5) . ?
N1 Zn2 2.082(3) . ?
N2 Zn1 2.029(3) 12_656 ?
N3 N4 1.354(5) . ?
N3 Zn1 2.336(4) 12_656 ?
N4 N5 1.304(5) . ?
N5 N6 1.362(4) . ?
N6 Zn1 1.988(3) . ?
N7 N8 1.358(4) . ?
N7 Zn1 2.088(3) . ?
N8 N9 1.308(4) . ?
N8 Zn1 2.103(3) 7_455 ?
N9 N10 1.343(4) . ?
N10 Zn2 2.232(3) . ?
O1 Zn2 2.095(6) . ?
O1 H1W 0.88(2) . ?
O2 Zn2 2.403(6) . ?
O2 H2W 0.85(2) . ?
Zn1 N2 2.029(3) 11_566 ?
Zn1 N8 2.103(3) 7_455 ?
Zn1 N3 2.336(4) 11_566 ?
Zn2 N1 2.082(3) 10_556 ?
Zn2 N10 2.232(3) 10_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 113.7(4) . . ?
N2 C1 H1 123.2 . . ?
N1 C1 H1 123.2 . . ?
C3 C2 N2 108.4(3) . . ?
C3 C2 C4 135.6(4) . . ?
N2 C2 C4 116.0(3) . . ?
C2 C3 N1 108.9(3) . . ?
C2 C3 C5 134.7(4) . . ?
N1 C3 C5 116.4(3) . . ?
N3 C4 N6 111.2(3) . . ?
N3 C4 C2 119.3(3) . . ?
N6 C4 C2 129.5(3) . . ?
N7 C5 N10 111.3(3) . . ?
N7 C5 C3 129.5(3) . . ?
N10 C5 C3 119.2(3) . . ?
C1 N1 C3 104.0(3) . . ?
C1 N1 Zn2 140.2(3) . . ?
C3 N1 Zn2 115.5(2) . . ?
C1 N2 C2 105.0(3) . . ?
C1 N2 Zn1 135.5(3) . 12_656 ?
C2 N2 Zn1 119.5(3) . 12_656 ?
C4 N3 N4 105.5(3) . . ?
C4 N3 Zn1 109.3(3) . 12_656 ?
N4 N3 Zn1 145.0(3) . 12_656 ?
N5 N4 N3 109.8(3) . . ?
N4 N5 N6 108.2(3) . . ?
C4 N6 N5 105.3(3) . . ?
C4 N6 Zn1 129.6(3) . . ?
N5 N6 Zn1 121.9(3) . . ?
C5 N7 N8 104.5(3) . . ?
C5 N7 Zn1 128.4(2) . . ?
N8 N7 Zn1 121.9(2) . . ?
N9 N8 N7 110.3(3) . . ?
N9 N8 Zn1 127.3(2) . 7_455 ?
N7 N8 Zn1 119.6(2) . 7_455 ?
N8 N9 N10 108.1(3) . . ?
C5 N10 N9 105.9(3) . . ?
C5 N10 Zn2 110.6(2) . . ?
N9 N10 Zn2 143.4(2) . . ?
Zn2 O1 H1W 118(4) . . ?
Zn2 O2 H2W 122(5) . . ?
N6 Zn1 N2 105.64(14) . 11_566 ?
N6 Zn1 N7 102.02(12) . . ?
N2 Zn1 N7 146.50(13) 11_566 . ?
N6 Zn1 N8 117.01(13) . 7_455 ?
N2 Zn1 N8 92.42(12) 11_566 7_455 ?
N7 Zn1 N8 91.55(12) . 7_455 ?
N6 Zn1 N3 103.39(13) . 11_566 ?
N2 Zn1 N3 75.67(13) 11_566 11_566 ?
N7 Zn1 N3 79.88(11) . 11_566 ?
N8 Zn1 N3 139.60(13) 7_455 11_566 ?
N1 Zn2 N1 102.53(18) . 10_556 ?
N1 Zn2 O1 98.69(14) . . ?
N1 Zn2 O1 98.69(14) 10_556 . ?
N1 Zn2 N10 78.12(12) . . ?
N1 Zn2 N10 166.25(14) 10_556 . ?
O1 Zn2 N10 94.75(13) . . ?
N1 Zn2 N10 166.25(14) . 10_556 ?
N1 Zn2 N10 78.12(12) 10_556 10_556 ?
O1 Zn2 N10 94.75(13) . 10_556 ?
N10 Zn2 N10 97.98(16) . 10_556 ?
N1 Zn2 O2 86.49(17) . . ?
N1 Zn2 O2 86.49(17) 10_556 . ?
O1 Zn2 O2 171.6(3) . . ?
N10 Zn2 O2 79.82(16) . . ?
N10 Zn2 O2 79.82(16) 10_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 N1 1.3(4) . . . . ?
C4 C2 C3 N1 -179.8(4) . . . . ?
N2 C2 C3 C5 178.0(4) . . . . ?
C4 C2 C3 C5 -3.1(8) . . . . ?
C3 C2 C4 N3 -177.2(4) . . . . ?
N2 C2 C4 N3 1.6(5) . . . . ?
C3 C2 C4 N6 2.3(7) . . . . ?
N2 C2 C4 N6 -178.9(4) . . . . ?
C2 C3 C5 N7 2.6(7) . . . . ?
N1 C3 C5 N7 179.2(4) . . . . ?
C2 C3 C5 N10 -174.8(4) . . . . ?
N1 C3 C5 N10 1.7(5) . . . . ?
N2 C1 N1 C3 0.7(5) . . . . ?
N2 C1 N1 Zn2 -172.5(3) . . . . ?
C2 C3 N1 C1 -1.2(4) . . . . ?
C5 C3 N1 C1 -178.6(4) . . . . ?
C2 C3 N1 Zn2 174.0(3) . . . . ?
C5 C3 N1 Zn2 -3.4(4) . . . . ?
N1 C1 N2 C2 0.0(5) . . . . ?
N1 C1 N2 Zn1 176.4(3) . . . 12_656 ?
C3 C2 N2 C1 -0.8(4) . . . . ?
C4 C2 N2 C1 -179.9(3) . . . . ?
C3 C2 N2 Zn1 -177.9(2) . . . 12_656 ?
C4 C2 N2 Zn1 3.0(4) . . . 12_656 ?
N6 C4 N3 N4 -0.9(5) . . . . ?
C2 C4 N3 N4 178.8(4) . . . . ?
N6 C4 N3 Zn1 175.9(3) . . . 12_656 ?
C2 C4 N3 Zn1 -4.5(4) . . . 12_656 ?
C4 N3 N4 N5 0.9(5) . . . . ?
Zn1 N3 N4 N5 -173.8(4) 12_656 . . . ?
N3 N4 N5 N6 -0.5(5) . . . . ?
N3 C4 N6 N5 0.6(4) . . . . ?
C2 C4 N6 N5 -179.0(4) . . . . ?
N3 C4 N6 Zn1 -159.1(3) . . . . ?
C2 C4 N6 Zn1 21.4(6) . . . . ?
N4 N5 N6 C4 0.0(5) . . . . ?
N4 N5 N6 Zn1 161.6(3) . . . . ?
N10 C5 N7 N8 0.8(4) . . . . ?
C3 C5 N7 N8 -176.8(4) . . . . ?
N10 C5 N7 Zn1 155.2(2) . . . . ?
C3 C5 N7 Zn1 -22.4(6) . . . . ?
C5 N7 N8 N9 -0.5(4) . . . . ?
Zn1 N7 N8 N9 -156.9(2) . . . . ?
C5 N7 N8 Zn1 161.8(2) . . . 7_455 ?
Zn1 N7 N8 Zn1 5.4(4) . . . 7_455 ?
N7 N8 N9 N10 0.0(4) . . . . ?
Zn1 N8 N9 N10 -160.7(2) 7_455 . . . ?
N7 C5 N10 N9 -0.9(4) . . . . ?
C3 C5 N10 N9 177.0(3) . . . . ?
N7 C5 N10 Zn2 -177.2(2) . . . . ?
C3 C5 N10 Zn2 0.6(4) . . . . ?
N8 N9 N10 C5 0.6(4) . . . . ?
N8 N9 N10 Zn2 174.8(3) . . . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.079



