# 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 2019

####################################################################### 
# 
# 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_exp_8183_tw
_database_code_depnum_ccdc_archive 'CCDC 1820496'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2019-01-03 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            'C26 H18 N7 O3 Zn'
_chemical_formula_weight         541.84

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'
O O 0.0492 0.0322 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1505(10)
_cell_length_b                   10.4512(11)
_cell_length_c                   13.869(2)
_cell_angle_alpha                108.994(13)
_cell_angle_beta                 101.343(12)
_cell_angle_gamma                97.790(9)
_cell_volume                     1200.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1706
_cell_measurement_theta_min      3.5300
_cell_measurement_theta_max      70.7050

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             554
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.792
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_T_min  0.97216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Enhance (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4297
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.488
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_full        67.250
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4297
_reflns_number_gt                3036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1118P)²+4.2726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4297
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2778
_refine_ls_wR_factor_gt          0.2567
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
Zn1 Zn 0.80796(14) 1.14769(11) 0.77770(9) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.6535(8) 0.9666(7) 0.6935(6) 0.0372(16) Uani 1 1 d . . . . .
N2 N 0.2473(8) 0.5307(7) 0.5643(5) 0.0347(16) Uani 1 1 d . . . . .
N3 N -0.1057(8) 0.2408(7) 0.6851(6) 0.0359(16) Uani 1 1 d . . . . .
N4 N 0.2322(10) 0.0454(9) -0.1303(7) 0.055(2) Uani 1 1 d . . . . .
N5 N 0.1711(10) -0.0209(9) -0.2355(7) 0.051(2) Uani 1 1 d . . . . .
N6 N 0.0360(10) 0.0034(8) -0.2636(6) 0.048(2) Uani 1 1 d . . . . .
N7 N 0.0009(8) 0.0834(7) -0.1780(6) 0.0386(17) Uani 1 1 d . . . . .
O1 O 0.5760(9) 1.2774(8) 0.7568(5) 0.0572(19) Uani 1 1 d . . . . .
O2 O 0.7465(8) 1.2730(7) 0.8921(5) 0.0508(17) Uani 1 1 d . . . . .
O3 O 0.2903(12) 0.1180(12) 0.6175(7) 0.104(4) Uani 1 1 d . . . . .
H3C H 0.2515 0.0771 0.6534 0.125 Uiso 1 1 d R U . . .
H3D H 0.3770 0.1680 0.6553 0.125 Uiso 1 1 d R U . . .
C1 C 0.5320(11) 0.9268(10) 0.7263(7) 0.048(2) Uani 1 1 d . . . . .
H1 H 0.5191 0.9844 0.7897 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4272(11) 0.8058(9) 0.6709(7) 0.044(2) Uani 1 1 d . . . . .
H2 H 0.3463 0.7809 0.6972 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4422(9) 0.7201(8) 0.5750(7) 0.0318(18) Uani 1 1 d . . . . .
C4 C 0.5647(10) 0.7606(9) 0.5409(7) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.5777 0.7057 0.4767 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6685(10) 0.8819(9) 0.6014(7) 0.040(2) Uani 1 1 d . . . . .
H5 H 0.7525 0.9064 0.5777 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3276(9) 0.5865(8) 0.5110(7) 0.0305(17) Uani 1 1 d . . . . .
C7 C 0.3055(10) 0.5301(8) 0.4031(7) 0.0361(19) Uani 1 1 d . . . . .
H7 H 0.3632 0.5735 0.3697 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1976(10) 0.4093(9) 0.3445(7) 0.0350(19) Uani 1 1 d . . . . .
C9 C 0.1098(10) 0.3531(8) 0.3998(7) 0.0349(19) Uani 1 1 d . . . . .
H9 H 0.0317 0.2749 0.3635 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1399(9) 0.4138(8) 0.5067(6) 0.0307(17) Uani 1 1 d . . . . .
C11 C 0.0541(9) 0.3544(8) 0.5697(6) 0.0297(17) Uani 1 1 d . . . . .
C12 C 0.0873(10) 0.4123(9) 0.6774(7) 0.040(2) Uani 1 1 d . . . . .
H12 H 0.1652 0.4906 0.7138 0.048 Uiso 1 1 calc R U . . .
C13 C 0.0052(11) 0.3545(9) 0.7319(7) 0.044(2) Uani 1 1 d . . . . .
H13 H 0.0284 0.3968 0.8050 0.053 Uiso 1 1 calc R U . . .
C14 C -0.1385(11) 0.1845(9) 0.5816(7) 0.042(2) Uani 1 1 d . . . . .
H14 H -0.2160 0.1053 0.5478 0.050 Uiso 1 1 calc R U . . .
C15 C -0.0638(11) 0.2364(9) 0.5202(7) 0.042(2) Uani 1 1 d . . . . .
H15 H -0.0917 0.1935 0.4471 0.050 Uiso 1 1 calc R U . . .
C16 C 0.1728(10) 0.3381(8) 0.2292(7) 0.0363(19) Uani 1 1 d . . . . .
C17 C 0.2982(10) 0.3364(10) 0.1852(7) 0.042(2) Uani 1 1 d . . . . .
H17 H 0.3945 0.3864 0.2275 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2803(11) 0.2614(10) 0.0799(7) 0.043(2) Uani 1 1 d . . . . .
H18 H 0.3653 0.2580 0.0526 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1384(11) 0.1917(9) 0.0150(7) 0.038(2) Uani 1 1 d . . . . .
C20 C 0.0116(11) 0.1968(10) 0.0565(7) 0.041(2) Uani 1 1 d . . . . .
H20 H -0.0851 0.1504 0.0131 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0297(10) 0.2707(9) 0.1624(7) 0.040(2) Uani 1 1 d . . . . .
H21 H -0.0558 0.2753 0.1892 0.048 Uiso 1 1 calc R U . . .
C22 C 0.1226(10) 0.1099(9) -0.0969(7) 0.0376(19) Uani 1 1 d . . . . .
C23 C 0.6320(11) 1.3134(9) 0.8530(8) 0.043(2) Uani 1 1 d . . . . .
C24 C 0.5638(11) 1.4104(9) 0.9305(7) 0.042(2) Uani 1 1 d . . . . .
C25 C 0.4278(11) 1.4457(11) 0.8939(8) 0.050(2) Uani 1 1 d . . . . .
H25 H 0.3787 1.4080 0.8223 0.060 Uiso 1 1 calc R U . . .
C26 C 0.3649(11) 1.5362(10) 0.9628(8) 0.049(2) Uani 1 1 d . . . . .
H26 H 0.2754 1.5610 0.9375 0.058 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 O2 1.935(6) . ?
Zn1 N7 2.027(8) 1_666 ?
Zn1 N1 2.032(7) . ?
Zn1 N3 2.056(7) 1_665 ?
N1 C5 1.341(11) . ?
N1 C1 1.346(11) . ?
N2 C6 1.344(10) . ?
N2 C10 1.352(10) . ?
N3 C14 1.315(11) . ?
N3 C13 1.332(11) . ?
N3 Zn1 2.056(7) 1_445 ?
N4 N5 1.355(12) . ?
N4 C22 1.355(12) . ?
N5 N6 1.305(12) . ?
N6 N7 1.337(10) . ?
N7 C22 1.343(11) . ?
N7 Zn1 2.027(8) 1_444 ?
O1 C23 1.239(11) . ?
O2 C23 1.271(11) . ?
O3 H3C 0.8500 . ?
O3 H3D 0.8501 . ?
C1 C2 1.364(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(12) . ?
C3 C6 1.505(11) . ?
C4 C5 1.372(12) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.380(12) . ?
C7 C8 1.381(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(11) . ?
C8 C16 1.483(12) . ?
C9 C10 1.363(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.501(10) . ?
C11 C12 1.369(12) . ?
C11 C15 1.397(12) . ?
C12 C13 1.378(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.384(12) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.384(12) . ?
C16 C17 1.401(12) . ?
C17 C18 1.378(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(13) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(13) . ?
C19 C22 1.474(12) . ?
C20 C21 1.383(12) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.516(13) . ?
C24 C26 1.382(13) 2_687 ?
C24 C25 1.393(14) . ?
C25 C26 1.384(13) . ?
C25 H25 0.9300 . ?
C26 C24 1.382(13) 2_687 ?
C26 H26 0.9300 . ?

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
O2 Zn1 N7 115.0(3) . 1_666 ?
O2 Zn1 N1 114.7(3) . . ?
N7 Zn1 N1 102.9(3) 1_666 . ?
O2 Zn1 N3 114.0(3) . 1_665 ?
N7 Zn1 N3 94.6(3) 1_666 1_665 ?
N1 Zn1 N3 113.5(3) . 1_665 ?
C5 N1 C1 117.1(7) . . ?
C5 N1 Zn1 120.7(6) . . ?
C1 N1 Zn1 122.2(6) . . ?
C6 N2 C10 116.6(7) . . ?
C14 N3 C13 117.3(7) . . ?
C14 N3 Zn1 123.5(6) . 1_445 ?
C13 N3 Zn1 118.5(6) . 1_445 ?
N5 N4 C22 103.8(8) . . ?
N6 N5 N4 110.6(7) . . ?
N5 N6 N7 109.1(8) . . ?
N6 N7 C22 105.9(7) . . ?
N6 N7 Zn1 109.6(6) . 1_444 ?
C22 N7 Zn1 142.9(6) . 1_444 ?
C23 O2 Zn1 108.5(6) . . ?
H3C O3 H3D 108.2 . . ?
N1 C1 C2 123.0(8) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.4(8) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 117.8(8) . . ?
C4 C3 C6 121.3(8) . . ?
C2 C3 C6 120.9(7) . . ?
C3 C4 C5 120.1(8) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 122.5(8) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
N2 C6 C7 123.3(7) . . ?
N2 C6 C3 116.4(7) . . ?
C7 C6 C3 120.3(7) . . ?
C6 C7 C8 120.0(8) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 116.7(8) . . ?
C7 C8 C16 123.3(7) . . ?
C9 C8 C16 120.0(7) . . ?
C10 C9 C8 119.7(7) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 123.5(7) . . ?
N2 C10 C11 114.8(7) . . ?
C9 C10 C11 121.7(7) . . ?
C12 C11 C15 116.9(8) . . ?
C12 C11 C10 122.0(7) . . ?
C15 C11 C10 121.1(7) . . ?
C11 C12 C13 120.0(8) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N3 C13 C12 123.1(8) . . ?
N3 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
N3 C14 C15 123.6(8) . . ?
N3 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
C14 C15 C11 119.0(8) . . ?
C14 C15 H15 120.5 . . ?
C11 C15 H15 120.5 . . ?
C21 C16 C17 118.1(8) . . ?
C21 C16 C8 122.6(8) . . ?
C17 C16 C8 119.4(8) . . ?
C18 C17 C16 120.6(8) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.8(8) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.3(8) . . ?
C18 C19 C22 119.7(8) . . ?
C20 C19 C22 120.9(8) . . ?
C21 C20 C19 120.0(8) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 121.1(8) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
N7 C22 N4 110.6(8) . . ?
N7 C22 C19 126.7(8) . . ?
N4 C22 C19 122.6(8) . . ?
O1 C23 O2 123.3(9) . . ?
O1 C23 C24 120.0(9) . . ?
O2 C23 C24 116.7(8) . . ?
C26 C24 C25 119.7(9) 2_687 . ?
C26 C24 C23 120.6(9) 2_687 . ?
C25 C24 C23 119.7(9) . . ?
C26 C25 C24 120.8(9) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C24 C26 C25 119.5(9) 2_687 . ?
C24 C26 H26 120.2 2_687 . ?
C25 C26 H26 120.2 . . ?

_refine_diff_density_max         1.711
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.152

