# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1452210'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_date             2016-02-07T20:13:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18  H30  N4  O4  Zn1'
_chemical_formula_sum            'C13 H18 N2 O4 Zn0.50'
_chemical_formula_weight         298.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2199(9)
_cell_length_b                   8.3508(10)
_cell_length_c                   11.2244(13)
_cell_angle_alpha                86.849(10)
_cell_angle_beta                 78.013(10)
_cell_angle_gamma                66.215(11)
_cell_volume                     689.30(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      3.7510
_cell_measurement_theta_max      26.9430
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314
_exptl_absorpt_correction_T_min  0.97129
_exptl_absorpt_correction_T_max  1.00000
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.946
_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.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      190(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.0696
_diffrn_reflns_number            5198
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.2984
_diffrn_reflns_theta_max         29.1678
_diffrn_measured_fraction_theta_max 0.5095
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_orient_matrix_UB_11      -0.0303919000
_diffrn_orient_matrix_UB_12      -0.0455619000
_diffrn_orient_matrix_UB_13      -0.0357334000
_diffrn_orient_matrix_UB_21      -0.0357693000
_diffrn_orient_matrix_UB_22      -0.0338138000
_diffrn_orient_matrix_UB_23      0.0536127000
_diffrn_orient_matrix_UB_31      -0.0840932000
_diffrn_orient_matrix_UB_32      0.0735230000
_diffrn_orient_matrix_UB_33      0.0051391000
_reflns_number_total             3117
_reflns_number_gt                2600
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_method       'ω scans'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SIR-97 (Altomare, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0229P)²+0.0819P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.079
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.4
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2435(3) -0.3960(3) -0.0078(2) 0.0267(5) Uani 1 d . .
C2 C 0.3061(4) -0.5653(3) 0.0307(2) 0.0365(6) Uani 1 d . .
C3 C 0.2211(3) -0.6044(3) 0.1408(2) 0.0330(6) Uani 1 d . .
C4 C 0.0730(3) -0.4722(3) 0.2102(2) 0.0228(5) Uani 1 d . .
C5 C 0.0205(3) -0.3061(3) 0.16382(19) 0.0215(5) Uani 1 d . .
C6 C -0.0350(3) -0.5028(3) 0.3286(2) 0.0266(5) Uani 1 d . .
C7 C -0.3207(3) -0.5365(3) 0.4192(2) 0.0234(5) Uani 1 d . .
C8 C -0.4080(3) -0.3847(3) 0.5128(2) 0.0269(5) Uani 1 d . .
C9 C -0.4662(3) -0.5771(3) 0.3793(2) 0.0280(5) Uani 1 d . .
C10 C 0.0971(3) 0.0279(3) 0.23792(19) 0.0192(5) Uani 1 d . .
C11 C 0.0459(3) 0.0135(3) 0.37393(18) 0.0197(5) Uani 1 d . .
C12 C 0.1613(3) 0.0155(3) 0.44868(19) 0.0211(5) Uani 1 d . .
C13 C -0.1158(3) -0.0015(3) 0.42628(19) 0.0207(5) Uani 1 d . .
N1 N 0.1014(2) -0.2658(2) 0.05803(16) 0.0216(4) Uani 1 d . .
N2 N -0.2094(3) -0.4966(3) 0.31040(17) 0.0249(4) Uani 1 d . .
O1 O -0.0311(2) 0.08141(19) 0.18068(13) 0.0239(3) Uani 1 d . .
O2 O 0.2611(2) -0.0139(2) 0.19077(13) 0.0290(4) Uani 1 d . .
O3 O -0.2761(2) 0.0312(2) 0.04906(17) 0.0256(4) Uani 1 d . .
O4 O -0.4004(3) -0.1413(3) 0.23653(18) 0.0396(5) Uani 1 d . .
Zn1 Zn 0 0 0 0.02085(12) Uani 1 d . .
H1 H 0.300(3) -0.361(3) -0.081(2) 0.026(6) Uiso 1 d . .
H1N H -0.185(3) -0.571(3) 0.258(2) 0.030(7) Uiso 1 d . .
H1O3 H -0.313(4) -0.022(3) 0.098(3) 0.045(9) Uiso 1 d . .
H1O4 H -0.510(5) -0.113(4) 0.238(3) 0.060(10) Uiso 1 d . .
H2 H 0.412(3) -0.656(3) -0.021(2) 0.039(7) Uiso 1 d . .
H2O3 H -0.292(5) 0.012(4) -0.024(4) 0.096(14) Uiso 1 d . .
H2O4 H -0.357(5) -0.250(4) 0.248(3) 0.077(12) Uiso 1 d . .
H3 H 0.265(3) -0.720(3) 0.168(2) 0.031(7) Uiso 1 d . .
H5 H -0.082(3) -0.213(3) 0.209(2) 0.023(6) Uiso 1 d . .
H6A H -0.067(3) -0.407(3) 0.388(2) 0.027(6) Uiso 1 d . .
H6B H 0.039(3) -0.615(3) 0.364(2) 0.027(6) Uiso 1 d . .
H7B H -0.245(3) -0.640(3) 0.4582(19) 0.020(6) Uiso 1 d . .
H8A H -0.320(4) -0.359(3) 0.541(2) 0.042(8) Uiso 1 d . .
H8B H -0.482(3) -0.279(3) 0.474(2) 0.028(6) Uiso 1 d . .
H9 H -0.411(3) -0.673(3) 0.320(2) 0.037(7) Uiso 1 d . .
H9A H -0.538(3) -0.482(3) 0.340(2) 0.026(6) Uiso 1 d . .
H12 H 0.268(3) 0.025(3) 0.418(2) 0.023(6) Uiso 1 d . .
H13 H -0.194(3) -0.004(3) 0.377(2) 0.032(7) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.341(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.95(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.98(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.383(3) . ?
C4 C6 1.508(3) . ?
C5 N1 1.332(3) . ?
C5 H5 0.95(2) . ?
C6 N2 1.470(3) . ?
C6 H6A 0.99(2) . ?
C6 H6B 1.00(2) . ?
C7 N2 1.476(3) . ?
C7 C9 1.521(3) . ?
C7 C8 1.524(3) . ?
C7 H7B 0.98(2) . ?
C8 C9 1.530(3) 2_446 ?
C8 H8A 0.95(3) . ?
C8 H8B 0.99(2) . ?
C9 C8 1.530(3) 2_446 ?
C9 H9 0.97(2) . ?
C9 H9A 0.93(2) . ?
C10 O2 1.250(2) . ?
C10 O1 1.262(2) . ?
C10 C11 1.509(3) . ?
C11 C13 1.389(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.387(3) 2_556 ?
C12 H12 0.90(2) . ?
C13 C12 1.387(3) 2_556 ?
C13 H13 0.94(3) . ?
N1 Zn1 2.1495(18) . ?
N2 H1N 0.82(2) . ?
O1 Zn1 2.1063(14) . ?
O3 Zn1 2.1315(17) . ?
O3 H1O3 0.77(3) . ?
O3 H2O3 0.89(4) . ?
O4 H1O4 0.83(3) . ?
O4 H2O4 0.84(3) . ?
Zn1 O1 2.1063(14) 2 ?
Zn1 O3 2.1315(17) 2 ?
Zn1 N1 2.1496(18) 2 ?

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
N1 C1 C2 122.3(2) . . ?
N1 C1 H1 114.8(13) . . ?
C2 C1 H1 122.9(13) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 119.0(15) . . ?
C3 C2 H2 121.6(15) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 119.7(14) . . ?
C4 C3 H3 120.9(14) . . ?
C5 C4 C3 116.9(2) . . ?
C5 C4 C6 119.56(19) . . ?
C3 C4 C6 123.5(2) . . ?
N1 C5 C4 124.58(19) . . ?
N1 C5 H5 116.6(13) . . ?
C4 C5 H5 118.8(13) . . ?
N2 C6 C4 110.23(19) . . ?
N2 C6 H6A 105.2(13) . . ?
C4 C6 H6A 110.2(13) . . ?
N2 C6 H6B 112.8(13) . . ?
C4 C6 H6B 110.1(13) . . ?
H6A C6 H6B 108.1(19) . . ?
N2 C7 C9 108.52(19) . . ?
N2 C7 C8 111.65(18) . . ?
C9 C7 C8 110.2(2) . . ?
N2 C7 H7B 110.1(12) . . ?
C9 C7 H7B 108.3(12) . . ?
C8 C7 H7B 108.0(12) . . ?
C7 C8 C9 110.95(19) . 2_446 ?
C7 C8 H8A 112.0(14) . . ?
C9 C8 H8A 109.7(16) 2_446 . ?
C7 C8 H8B 108.7(13) . . ?
C9 C8 H8B 108.2(13) 2_446 . ?
H8A C8 H8B 107.2(19) . . ?
C7 C9 C8 112.1(2) . 2_446 ?
C7 C9 H9 110.2(15) . . ?
C8 C9 H9 111.1(14) 2_446 . ?
C7 C9 H9A 110.1(14) . . ?
C8 C9 H9A 107.6(14) 2_446 . ?
H9 C9 H9A 106(2) . . ?
O2 C10 O1 125.20(19) . . ?
O2 C10 C11 118.24(19) . . ?
O1 C10 C11 116.55(18) . . ?
C13 C11 C12 119.3(2) . . ?
C13 C11 C10 120.7(2) . . ?
C12 C11 C10 119.98(19) . . ?
C13 C12 C11 120.4(2) 2_556 . ?
C13 C12 H12 117.6(15) 2_556 . ?
C11 C12 H12 122.0(15) . . ?
C12 C13 C11 120.3(2) 2_556 . ?
C12 C13 H13 119.5(15) 2_556 . ?
C11 C13 H13 120.2(15) . . ?
C5 N1 C1 117.44(19) . . ?
C5 N1 Zn1 119.42(14) . . ?
C1 N1 Zn1 123.14(15) . . ?
C6 N2 C7 114.55(19) . . ?
C6 N2 H1N 106.3(18) . . ?
C7 N2 H1N 107.4(17) . . ?
C10 O1 Zn1 123.03(13) . . ?
Zn1 O3 H1O3 125(2) . . ?
Zn1 O3 H2O3 99(2) . . ?
H1O3 O3 H2O3 111(3) . . ?
H1O4 O4 H2O4 105(3) . . ?
O1 Zn1 O1 180.00(8) . 2 ?
O1 Zn1 O3 86.31(7) . . ?
O1 Zn1 O3 93.68(7) 2 . ?
O1 Zn1 O3 93.69(7) . 2 ?
O1 Zn1 O3 86.32(7) 2 2 ?
O3 Zn1 O3 180 . 2 ?
O1 Zn1 N1 88.11(6) . . ?
O1 Zn1 N1 91.89(6) 2 . ?
O3 Zn1 N1 93.27(7) . . ?
O3 Zn1 N1 86.73(7) 2 . ?
O1 Zn1 N1 91.89(6) . 2 ?
O1 Zn1 N1 88.11(6) 2 2 ?
O3 Zn1 N1 86.73(7) . 2 ?
O3 Zn1 N1 93.27(7) 2 2 ?
N1 Zn1 N1 180 . 2 ?

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
N1 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C6 176.8(2) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C6 C4 C5 N1 -177.2(2) . . . . ?
C5 C4 C6 N2 72.9(3) . . . . ?
C3 C4 C6 N2 -104.5(3) . . . . ?
N2 C7 C8 C9 175.9(2) . . . 2_446 ?
C9 C7 C8 C9 55.2(3) . . . 2_446 ?
N2 C7 C9 C8 -178.41(19) . . . 2_446 ?
C8 C7 C9 C8 -55.9(3) . . . 2_446 ?
O2 C10 C11 C13 -157.7(2) . . . . ?
O1 C10 C11 C13 22.1(3) . . . . ?
O2 C10 C11 C12 22.4(3) . . . . ?
O1 C10 C11 C12 -157.78(19) . . . . ?
C13 C11 C12 C13 0.5(3) . . . 2_556 ?
C10 C11 C12 C13 -179.70(18) . . . 2_556 ?
C12 C11 C13 C12 -0.5(3) . . . 2_556 ?
C10 C11 C13 C12 179.70(18) . . . 2_556 ?
C4 C5 N1 C1 0.1(3) . . . . ?
C4 C5 N1 Zn1 179.72(17) . . . . ?
C2 C1 N1 C5 -0.3(3) . . . . ?
C2 C1 N1 Zn1 -179.83(19) . . . . ?
C4 C6 N2 C7 176.18(18) . . . . ?
C9 C7 N2 C6 -163.8(2) . . . . ?
C8 C7 N2 C6 74.5(3) . . . . ?
O2 C10 O1 Zn1 31.4(3) . . . . ?
C11 C10 O1 Zn1 -148.37(13) . . . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF and water'
_chemical_properties_physical    Photo-sensitive
