# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_HPU-1
_database_code_depnum_ccdc_archive 'CCDC 1542239'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22.50 H20.50 N5.50 O6.50 Zn'
_chemical_formula_weight         537.31

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/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                   12.208(3)
_cell_length_b                   13.002(3)
_cell_length_c                   16.101(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.197(4)
_cell_angle_gamma                90
_cell_volume                     2477.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4987
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.041
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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            15212
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         28.224
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5915
_reflns_number_gt                3889
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5915
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.24494(2) -0.43375(2) 1.16949(2) 0.04324(11) Uani 1 1 d . . . . .
N1 N 0.26843(17) 0.44563(15) 1.09315(13) 0.0460(5) Uani 1 1 d . . . . .
N2 N 0.29366(16) 0.09761(15) 0.95231(13) 0.0457(5) Uani 1 1 d . . . . .
N3 N 0.34209(18) 0.03160(16) 0.90742(14) 0.0522(5) Uani 1 1 d . . . . .
N4 N 0.41048(17) 0.19177(16) 0.90261(15) 0.0552(6) Uani 1 1 d . . . . .
N5 N 0.62608(16) -0.01327(16) 0.72728(13) 0.0465(5) Uani 1 1 d . . . . .
O1 O -0.10949(16) -0.04878(16) 0.75428(12) 0.0651(5) Uani 1 1 d . . . . .
O2 O -0.18338(16) -0.17731(15) 0.81001(12) 0.0651(5) Uani 1 1 d . . . . .
O3 O 0.07249(17) -0.37342(15) 1.04388(14) 0.0732(6) Uani 1 1 d . . . . .
O4 O 0.23130(16) -0.30379(14) 1.11106(11) 0.0616(5) Uani 1 1 d . . . . .
C1 C -0.1072(2) -0.1157(2) 0.81175(16) 0.0483(6) Uani 1 1 d . . . . .
C2 C -0.0051(2) -0.11563(19) 0.88542(15) 0.0430(6) Uani 1 1 d . . . . .
C3 C 0.0198(2) -0.20249(18) 0.93477(14) 0.0425(5) Uani 1 1 d . . . . .
H3 H -0.0264 -0.2600 0.9212 0.051 Uiso 1 1 calc R U . . .
C4 C 0.11123(19) -0.20599(18) 1.00348(15) 0.0422(5) Uani 1 1 d . . . . .
C5 C 0.1386(2) -0.3022(2) 1.05568(16) 0.0484(6) Uani 1 1 d . . . . .
C6 C 0.1785(2) -0.1191(2) 1.02389(15) 0.0471(6) Uani 1 1 d . . . . .
H6 H 0.2413 -0.1211 1.0702 0.057 Uiso 1 1 calc R U . . .
C7 C 0.1541(2) -0.03067(19) 0.97713(16) 0.0440(6) Uani 1 1 d . . . . .
C8 C 0.0631(2) -0.02858(19) 0.90729(16) 0.0478(6) Uani 1 1 d . . . . .
H8 H 0.0469 0.0309 0.8745 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2245(3) 0.0634(2) 1.00795(18) 0.0598(7) Uani 1 1 d . . . . .
H9A H 0.1745 0.1191 1.0146 0.072 Uiso 1 1 calc R U . . .
H9B H 0.2733 0.0489 1.0640 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5563(2) -0.0771(2) 0.7523(2) 0.0636(8) Uani 1 1 d . . . . .
H10 H 0.5559 -0.1459 0.7362 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4845(2) -0.0463(2) 0.8009(2) 0.0643(8) Uani 1 1 d . . . . .
H11 H 0.4371 -0.0936 0.8178 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4834(2) 0.05529(19) 0.82443(17) 0.0479(6) Uani 1 1 d . . . . .
C13 C 0.5547(2) 0.12206(19) 0.79693(17) 0.0523(6) Uani 1 1 d . . . . .
H13 H 0.5553 0.1916 0.8106 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6247(2) 0.08504(19) 0.74928(17) 0.0494(6) Uani 1 1 d . . . . .
H14 H 0.6733 0.1305 0.7316 0.059 Uiso 1 1 calc R U . . .
C15 C 0.4110(2) 0.09230(19) 0.87848(17) 0.0476(6) Uani 1 1 d . . . . .
C16 C 0.33701(19) 0.19208(19) 0.94924(16) 0.0455(6) Uani 1 1 d . . . . .
C17 C 0.3100(2) 0.28022(18) 0.99702(16) 0.0455(6) Uani 1 1 d . . . . .
C18 C 0.3907(3) 0.3177(3) 1.0636(2) 0.0912(12) Uani 1 1 d . . . . .
H18 H 0.4621 0.2879 1.0775 0.109 Uiso 1 1 calc R U . . .
C19 C 0.3677(3) 0.3988(3) 1.1101(2) 0.0914(12) Uani 1 1 d . . . . .
H19 H 0.4244 0.4223 1.1559 0.110 Uiso 1 1 calc R U . . .
C20 C 0.2073(2) 0.3272(2) 0.98055(18) 0.0557(7) Uani 1 1 d . . . . .
H20 H 0.1485 0.3034 0.9365 0.067 Uiso 1 1 calc R U . . .
C21 C 0.1908(2) 0.40977(19) 1.02911(18) 0.0530(7) Uani 1 1 d . . . . .
H21 H 0.1206 0.4419 1.0156 0.064 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 1.9213(18) . ?
Zn1 O1 1.9708(19) 4_656 ?
Zn1 N5 2.0269(19) 4_556 ?
Zn1 N1 2.056(2) 1_545 ?
N1 C21 1.303(3) . ?
N1 C19 1.324(3) . ?
N1 Zn1 2.056(2) 1_565 ?
N2 C16 1.343(3) . ?
N2 N3 1.348(3) . ?
N2 C9 1.444(3) . ?
N3 C15 1.319(3) . ?
N4 C16 1.303(3) . ?
N4 C15 1.351(3) . ?
N5 C10 1.321(3) . ?
N5 C14 1.327(3) . ?
N5 Zn1 2.0270(19) 4_655 ?
O1 C1 1.266(3) . ?
O1 Zn1 1.9708(19) 4 ?
O2 C1 1.223(3) . ?
O3 C5 1.212(3) . ?
O4 C5 1.257(3) . ?
C1 C2 1.495(4) . ?
C2 C3 1.371(3) . ?
C2 C8 1.398(3) . ?
C3 C4 1.366(3) . ?
C4 C6 1.388(3) . ?
C4 C5 1.498(3) . ?
C6 C7 1.366(3) . ?
C7 C8 1.374(3) . ?
C7 C9 1.507(3) . ?
C10 C11 1.370(4) . ?
C11 C12 1.375(3) . ?
C12 C13 1.377(3) . ?
C12 C15 1.466(3) . ?
C13 C14 1.369(3) . ?
C16 C17 1.462(3) . ?
C17 C20 1.360(3) . ?
C17 C18 1.356(4) . ?
C18 C19 1.362(4) . ?
C20 C21 1.372(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
O4 Zn1 O1 113.31(8) . 4_656 ?
O4 Zn1 N5 122.54(8) . 4_556 ?
O1 Zn1 N5 105.56(8) 4_656 4_556 ?
O4 Zn1 N1 112.72(8) . 1_545 ?
O1 Zn1 N1 95.28(8) 4_656 1_545 ?
N5 Zn1 N1 103.64(8) 4_556 1_545 ?
C21 N1 C19 116.7(2) . . ?
C21 N1 Zn1 124.41(17) . 1_565 ?
C19 N1 Zn1 118.83(18) . 1_565 ?
C16 N2 N3 109.50(19) . . ?
C16 N2 C9 126.9(2) . . ?
N3 N2 C9 122.4(2) . . ?
C15 N3 N2 102.12(19) . . ?
C16 N4 C15 102.8(2) . . ?
C10 N5 C14 118.2(2) . . ?
C10 N5 Zn1 120.94(17) . 4_655 ?
C14 N5 Zn1 120.44(16) . 4_655 ?
C1 O1 Zn1 106.38(17) . 4 ?
C5 O4 Zn1 108.45(16) . . ?
O2 C1 O1 123.6(3) . . ?
O2 C1 C2 120.0(2) . . ?
O1 C1 C2 116.4(2) . . ?
C3 C2 C8 119.1(2) . . ?
C3 C2 C1 118.8(2) . . ?
C8 C2 C1 122.0(2) . . ?
C2 C3 C4 121.2(2) . . ?
C3 C4 C6 118.9(2) . . ?
C3 C4 C5 120.5(2) . . ?
C6 C4 C5 120.6(2) . . ?
O3 C5 O4 123.2(2) . . ?
O3 C5 C4 120.1(2) . . ?
O4 C5 C4 116.7(2) . . ?
C7 C6 C4 121.2(2) . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 C9 118.2(2) . . ?
C8 C7 C9 122.3(2) . . ?
C7 C8 C2 120.2(2) . . ?
N2 C9 C7 114.8(2) . . ?
N5 C10 C11 122.7(2) . . ?
C10 C11 C12 119.3(2) . . ?
C13 C12 C11 117.8(2) . . ?
C13 C12 C15 120.3(2) . . ?
C11 C12 C15 121.8(2) . . ?
C12 C13 C14 119.3(2) . . ?
N5 C14 C13 122.6(2) . . ?
N3 C15 N4 115.0(2) . . ?
N3 C15 C12 122.9(2) . . ?
N4 C15 C12 122.1(2) . . ?
N4 C16 N2 110.6(2) . . ?
N4 C16 C17 125.6(2) . . ?
N2 C16 C17 123.7(2) . . ?
C20 C17 C18 116.7(2) . . ?
C20 C17 C16 124.4(2) . . ?
C18 C17 C16 118.9(2) . . ?
C19 C18 C17 120.4(3) . . ?
N1 C19 C18 122.9(3) . . ?
C17 C20 C21 119.8(2) . . ?
N1 C21 C20 123.4(2) . . ?

_refine_diff_density_max         0.684
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3



