# 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_Zn
_database_code_depnum_ccdc_archive 'CCDC 1575366'
_audit_update_record             
;
2018-01-03 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;
_audit_creation_date             2017-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C48 H24 N24 O16 Zn4), 2(C3 H7 N O)'
_chemical_formula_sum            'C18 H20 N8 O6 Zn'
_chemical_formula_weight         509.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Zn'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.4591(5)
_cell_length_b                   16.6924(5)
_cell_length_c                   13.1556(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.234(4)
_cell_angle_gamma                90
_cell_volume                     2468.19(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2324
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      72.1870
_cell_measurement_theta_min      4.7160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4731
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.202
_diffrn_reflns_theta_min         4.743
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  32.00   1.00    1.44    --  -39.90  38.00  90.00   80
  2  ω    -66.00  34.00   1.00    1.44    --  -39.90  57.00-180.00  100
  3  ω     65.00  97.00   1.00    1.44    --   39.90-125.00-180.00   32
  4  ω     51.00 122.00   1.00    5.75    --  106.29-125.00-120.00   71
  5  ω     54.00 125.00   1.00    5.75    --  106.29 -45.00  60.00   71
  6  ω     77.00 112.00   1.00    5.75    --  106.29  30.00-120.00   35
  7  ω    115.00 174.00   1.00    5.75    --  106.29  30.00-120.00   59
  8  ω    100.00 137.00   1.00    5.75    --  106.29 125.00-120.00   37
  9  ω     96.00 123.00   1.00    5.75    --  106.29 125.00 120.00   27
 10  ω     32.00 109.00   1.00    5.75    --  106.29 -94.00  90.00   77
 11  ω     37.00 128.00   1.00    5.75    --  106.29-152.00  91.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1149639000
_diffrn_orient_matrix_UB_12      0.0364778000
_diffrn_orient_matrix_UB_13      -0.0637599000
_diffrn_orient_matrix_UB_21      -0.0425918000
_diffrn_orient_matrix_UB_22      -0.0842606000
_diffrn_orient_matrix_UB_23      -0.0381385000
_diffrn_orient_matrix_UB_31      -0.0613873000
_diffrn_orient_matrix_UB_32      -0.0096132000
_diffrn_orient_matrix_UB_33      0.0934267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus 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                2134
_reflns_number_total             2402
_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.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+13.8364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C1(H1), C9(H9)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn01 Zn 0.500000 0.58207(3) 0.250000 0.02125(18) Uani 1 2 d S T P . .
O1 O 0.4258(2) 0.65990(13) 0.32821(17) 0.0288(5) Uani 1 1 d . . . . .
N3 N 0.2056(2) 0.89956(15) 0.40194(19) 0.0221(5) Uani 1 1 d . . . . .
N1 N 0.1230(2) 1.00570(15) 0.32554(19) 0.0247(5) Uani 1 1 d . . . . .
O2 O 0.3668(3) 0.55876(15) 0.4133(2) 0.0540(9) Uani 1 1 d . . . . .
C6 C 0.3748(3) 0.63049(18) 0.3964(2) 0.0254(6) Uani 1 1 d . . . . .
C2 C 0.1044(3) 0.93762(18) 0.3710(2) 0.0257(6) Uani 1 1 d . . . . .
H2 H 0.030382 0.919228 0.379810 0.031 Uiso 1 1 calc R . . . .
C3 C 0.2273(3) 0.82422(18) 0.4547(2) 0.0216(6) Uani 1 1 d . . . . .
C4 C 0.2901(3) 0.76750(18) 0.4105(2) 0.0227(6) Uani 1 1 d . . . . .
H4 H 0.316650 0.780212 0.350036 0.027 Uiso 1 1 calc R . . . .
N2 N 0.2967(3) 0.9419(2) 0.3758(3) 0.0544(10) Uani 1 1 d . . . . .
C5 C 0.3146(3) 0.69187(18) 0.4542(2) 0.0219(6) Uani 1 1 d . . . . .
C1 C 0.2423(4) 1.0054(3) 0.3311(4) 0.0538(12) Uani 1 1 d . . . . .
H1 H 0.282251 1.046921 0.305374 0.065 Uiso 1 1 calc R . . . .
O3 O 0.3738(4) 0.3328(3) 0.3730(5) 0.1108(18) Uani 1 1 d . . . . .
N4 N 0.1894(4) 0.3539(3) 0.4023(4) 0.0788(16) Uani 1 1 d . . . . .
C9 C 0.2979(5) 0.3771(3) 0.3949(5) 0.0701(15) Uani 1 1 d . . . . .
H9 H 0.317574 0.430784 0.407359 0.084 Uiso 1 1 calc R . . . .
C8 C 0.1488(8) 0.2747(5) 0.3829(5) 0.136(4) Uani 1 1 d . . . . .
H8A H 0.088740 0.273293 0.320869 0.205 Uiso 1 1 calc GR . . . .
H8B H 0.115850 0.255756 0.440223 0.205 Uiso 1 1 calc GR . . . .
H8C H 0.214126 0.240978 0.374446 0.205 Uiso 1 1 calc GR . . . .
C7 C 0.1021(7) 0.4141(7) 0.4196(8) 0.158(5) Uani 1 1 d . . . . .
H7A H 0.141831 0.463899 0.439573 0.236 Uiso 1 1 calc GR . . . .
H7B H 0.062790 0.396136 0.473566 0.236 Uiso 1 1 calc GR . . . .
H7C H 0.044332 0.421612 0.356827 0.236 Uiso 1 1 calc GR . . . .


_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
Zn01 O1 1.952(2) 2_655 ?
Zn01 O1 1.952(2) . ?
Zn01 N1 2.013(3) 3_545 ?
Zn01 N1 2.013(3) 4_545 ?
O1 C6 1.261(4) . ?
N3 C2 1.315(4) . ?
N3 C3 1.434(4) . ?
N3 N2 1.360(4) . ?
N1 C2 1.320(4) . ?
N1 C1 1.355(5) . ?
O2 C6 1.225(4) . ?
C6 C5 1.520(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 C5 1.402(4) 7_566 ?
C4 H4 0.9300 . ?
C4 C5 1.393(4) . ?
N2 C1 1.310(5) . ?
C1 H1 0.9300 . ?
O3 C9 1.219(7) . ?
N4 C9 1.324(6) . ?
N4 C8 1.409(8) . ?
N4 C7 1.467(10) . ?
C9 H9 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O1 Zn01 O1 96.55(13) 2_655 . ?
O1 Zn01 N1 119.74(10) . 3_545 ?
O1 Zn01 N1 119.74(10) 2_655 4_545 ?
O1 Zn01 N1 110.30(10) . 4_545 ?
O1 Zn01 N1 110.30(10) 2_655 3_545 ?
N1 Zn01 N1 101.41(15) 4_545 3_545 ?
C6 O1 Zn01 115.17(19) . . ?
C2 N3 C3 129.3(3) . . ?
C2 N3 N2 110.2(3) . . ?
N2 N3 C3 120.6(3) . . ?
C2 N1 Zn01 127.5(2) . 3_455 ?
C2 N1 C1 102.9(3) . . ?
C1 N1 Zn01 129.1(2) . 3_455 ?
O1 C6 C5 114.3(3) . . ?
O2 C6 O1 124.9(3) . . ?
O2 C6 C5 120.7(3) . . ?
N3 C2 N1 110.2(3) . . ?
N3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
C4 C3 N3 116.9(2) . . ?
C4 C3 C5 121.4(3) . 7_566 ?
C5 C3 N3 121.7(3) 7_566 . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C1 N2 N3 102.2(3) . . ?
C3 C5 C6 124.3(3) 7_566 . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 C3 116.8(3) . 7_566 ?
N1 C1 H1 122.8 . . ?
N2 C1 N1 114.5(3) . . ?
N2 C1 H1 122.8 . . ?
C9 N4 C8 122.9(6) . . ?
C9 N4 C7 119.4(6) . . ?
C8 N4 C7 117.3(7) . . ?
O3 C9 N4 124.3(5) . . ?
O3 C9 H9 117.9 . . ?
N4 C9 H9 117.9 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_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 0.355 0.750 103.0 28.8 ?
2 0.000 0.645 0.250 103.0 29.0 ?
3 0.500 0.145 0.250 103.0 29.0 ?
4 0.500 0.855 0.750 103.0 28.8 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.821
_oxdiff_exptl_absorpt_empirical_full_min 0.238
