# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_GoldsmithSK071221c
_database_code_depnum_ccdc_archive 'CCDC 2173563'
loop_
_audit_author_name
_audit_author_address
'P. Raj Pokkuluri'
;Auburn University
United States of America
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-08-29 downloaded from the CCDC.
;
_chemical_name_systematic        
'(1-(2,5-dihydroxybenzyl)-8-(2,5-dihydroxybenzylalkoxide)-1,4,8,11-tetraazacyclotetradecane)zinc(II) triflate'
_chemical_name_common            '[Zn(H3qp4)](OTf)'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H35 F3 N4 O7 S Zn'
_chemical_formula_iupac          ?
_chemical_formula_weight         658.00

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4279(5)
_cell_length_b                   14.3589(7)
_cell_length_c                   21.7932(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.919(2)
_cell_angle_gamma                90
_cell_volume                     2896.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9753
_cell_measurement_theta_min      2.3739
_cell_measurement_theta_max      26.2417
_cell_measurement_temperature    306.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368

_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      306.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            74846
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
;

_reflns_number_total             5940
_reflns_number_gt                5147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0915
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         5940
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.3919P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.383
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.67652(2) 0.22066(2) 0.39160(2) 0.03777(8) Uani d . . . 1 . .
C C1 0.7060(2) 0.43268(16) 0.35450(11) 0.0504(5) Uani d . . . 1 . .
H H1A 0.689718 0.496439 0.366139 0.06 Uiso calc U . R 1 . .
H H1AB 0.677446 0.428287 0.309437 0.06 Uiso calc U . R 1 . .
N N1 0.60957(18) 0.37070(11) 0.38336(7) 0.0374(3) Uani d . . . 1 . .
O O1 0.54589(16) 0.18378(9) 0.31596(6) 0.0435(3) Uani d . . . 1 . .
F F1 0.1308(2) 0.34628(13) 0.65812(8) 0.0882(5) Uani d . . . 1 . .
S S1 0.12037(7) 0.29225(4) 0.54372(3) 0.05638(15) Uani d . . . 1 . .
F F3 0.3209(3) 0.2825(3) 0.64246(16) 0.1765(15) Uani d . . . 1 . .
O O3 0.25557(19) 0.39618(11) 0.42287(9) 0.0600(4) Uani d . . . 1 . .
H H3 0.215(4) 0.4108(7) 0.4519(15) 0.09 Uiso calc U . R 1 . .
C C3 0.9183(3) 0.32133(18) 0.34930(12) 0.0566(6) Uani d . . . 1 . .
H H3A 0.869127 0.310203 0.306658 0.068 Uiso calc U . R 1 . .
H H3AB 1.021123 0.32506 0.349467 0.068 Uiso calc U . R 1 . .
N N3 0.7516(2) 0.06963(12) 0.40812(8) 0.0471(4) Uani d . . . 1 . .
F F2 0.1396(4) 0.20035(16) 0.64688(13) 0.1512(12) Uani d . . . 1 . .
O O2 0.2116(2) -0.13306(13) 0.31163(10) 0.0651(5) Uani d . . . 1 . .
H H5 0.264(4) -0.175(3) 0.3109(19) 0.112(15) Uiso d . . . 1 . .
C C2 0.8671(3) 0.41261(16) 0.37196(13) 0.0574(6) Uani d . . . 1 . .
H H2A 0.918415 0.462682 0.355711 0.069 Uiso calc U . R 1 . .
H H2AB 0.894612 0.414177 0.41715 0.069 Uiso calc U . R 1 . .
N N2 0.8901(2) 0.24305(14) 0.38911(10) 0.0479(4) Uani d . . . 1 . .
H H2 0.932(3) 0.2551(19) 0.4254(13) 0.056(7) Uiso d . . . 1 . .
O O4 0.3445(2) 0.70589(10) 0.28503(9) 0.0586(4) Uani d . . . 1 . .
H H4 0.391(4) 0.6914(7) 0.2565(15) 0.088 Uiso calc U . R 1 . .
C C4 0.9538(3) 0.15332(18) 0.37397(13) 0.0600(6) Uani d . . . 1 . .
H H4A 1.058221 0.158489 0.380968 0.072 Uiso calc U . R 1 . .
H H4AB 0.919261 0.137986 0.330354 0.072 Uiso calc U . R 1 . .
N N4 0.6544(2) 0.23654(13) 0.48357(8) 0.0447(4) Uani d . . . 1 . .
H H1 0.737(3) 0.2547(18) 0.5040(12) 0.053(7) Uiso d . . . 1 . .
O O5 0.1948(3) 0.22281(15) 0.51577(13) 0.1023(8) Uani d . . . 1 . .
C C5 0.9108(3) 0.07758(17) 0.41513(13) 0.0621(6) Uani d . . . 1 . .
H H5A 0.949703 0.018519 0.404391 0.075 Uiso calc U . R 1 . .
H H5AB 0.952304 0.091039 0.458424 0.075 Uiso calc U . R 1 . .
O O7 -0.0303(2) 0.2780(2) 0.53617(12) 0.1012(8) Uani d . . . 1 . .
C C7 0.7189(3) 0.07700(18) 0.52112(11) 0.0640(7) Uani d . . . 1 . .
H H7A 0.705173 0.03584 0.554802 0.077 Uiso calc U . R 1 . .
H H7AB 0.814701 0.103855 0.53245 0.077 Uiso calc U . R 1 . .
O O6 0.1563(3) 0.38702(15) 0.53227(11) 0.1061(9) Uani d . . . 1 . .
C C6 0.7127(3) 0.01940(16) 0.46239(11) 0.0600(6) Uani d . . . 1 . .
H H6A 0.777296 -0.033315 0.472287 0.072 Uiso calc U . R 1 . .
H H6AB 0.615528 -0.005017 0.450002 0.072 Uiso calc U . R 1 . .
C C9 0.5606(2) 0.31906(16) 0.48557(10) 0.0483(5) Uani d . . . 1 . .
H H9A 0.563703 0.337929 0.528538 0.058 Uiso calc U . R 1 . .
H H9AB 0.461493 0.304043 0.466979 0.058 Uiso calc U . R 1 . .
C C8 0.6091(3) 0.15465(18) 0.51604(12) 0.0612(6) Uani d . . . 1 . .
H H8A 0.516762 0.132428 0.49337 0.073 Uiso calc U . R 1 . .
H H8AB 0.596746 0.172734 0.557588 0.073 Uiso calc U . R 1 . .
C C15 0.2327(3) 0.02980(16) 0.30025(11) 0.0512(5) Uani d . . . 1 . .
H H15 0.132663 0.033523 0.289296 0.061 Uiso calc U . R 1 . .
C C16 0.2988(3) -0.05580(14) 0.31452(10) 0.0469(5) Uani d . . . 1 . .
C C17 0.4470(2) -0.06041(14) 0.33129(9) 0.0448(5) Uani d . . . 1 . .
H H17 0.491189 -0.117791 0.341162 0.054 Uiso calc U . R 1 . .
C C18 0.4583(2) 0.37707(13) 0.34643(9) 0.0390(4) Uani d . . . 1 . .
H H18A 0.402059 0.327105 0.359908 0.047 Uiso calc U . R 1 . .
H H18B 0.461687 0.366045 0.302824 0.047 Uiso calc U . R 1 . .
C C19 0.3786(2) 0.46768(13) 0.35079(9) 0.0384(4) Uani d . . . 1 . .
C C20 0.4002(2) 0.54583(14) 0.31549(9) 0.0419(4) Uani d . . . 1 . .
H H20 0.467037 0.542842 0.289173 0.05 Uiso calc U . R 1 . .
C C21 0.3243(2) 0.62762(14) 0.31884(9) 0.0434(4) Uani d . . . 1 . .
C C22 0.2243(2) 0.63243(15) 0.35772(10) 0.0467(5) Uani d . . . 1 . .
H H22 0.172806 0.687125 0.360098 0.056 Uiso calc U . R 1 . .
C C23 0.2011(2) 0.55619(16) 0.39294(10) 0.0472(5) Uani d . . . 1 . .
H H23 0.133803 0.559624 0.41903 0.057 Uiso calc U . R 1 . .
C C24 0.2775(2) 0.47431(14) 0.38971(10) 0.0427(4) Uani d . . . 1 . .
C C25 0.1832(3) 0.2809(2) 0.62710(16) 0.0750(8) Uani d . . . 1 . .
C C14 0.3153(2) 0.10944(14) 0.30226(10) 0.0474(5) Uani d . . . 1 . .
H H14 0.269718 0.16652 0.292818 0.057 Uiso calc U . R 1 . .
C C13 0.4653(2) 0.10615(13) 0.31813(8) 0.0399(4) Uani d . . . 1 . .
C C12 0.5317(2) 0.01945(13) 0.33372(9) 0.0418(4) Uani d . . . 1 . .
C C11 0.6931(2) 0.01558(15) 0.35015(11) 0.0493(5) Uani d . . . 1 . .
H H11A 0.723488 -0.048852 0.356179 0.059 Uiso calc U . R 1 . .
H H11B 0.733175 0.040381 0.315681 0.059 Uiso calc U . R 1 . .
C C10 0.6150(2) 0.39713(14) 0.44958(9) 0.0447(5) Uani d . . . 1 . .
H H10A 0.556282 0.452193 0.451327 0.054 Uiso calc U . R 1 . .
H H10B 0.713685 0.412183 0.468865 0.054 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 . 1.9353(14) ?
Zn1 N2 . 2.0500(19) ?
Zn1 N4 . 2.0666(18) ?
Zn1 N1 . 2.2426(16) ?
Zn1 N3 . 2.2883(17) ?
C1 N1 . 1.494(3) ?
C1 C2 . 1.522(3) ?
N1 C10 . 1.484(2) ?
N1 C18 . 1.502(2) ?
O1 C13 . 1.355(2) ?
F1 C25 . 1.308(3) ?
S1 O7 . 1.414(2) ?
S1 O5 . 1.421(2) ?
S1 O6 . 1.436(2) ?
S1 C25 . 1.809(3) ?
F3 C25 . 1.278(4) ?
O3 C24 . 1.371(2) ?
C3 N2 . 1.474(3) ?
C3 C2 . 1.512(3) ?
N3 C5 . 1.484(3) ?
N3 C6 . 1.489(3) ?
N3 C11 . 1.496(3) ?
F2 C25 . 1.326(4) ?
O2 C16 . 1.375(3) ?
N2 C4 . 1.485(3) ?
O4 C21 . 1.377(2) ?
C4 C5 . 1.513(4) ?
N4 C8 . 1.477(3) ?
N4 C9 . 1.484(3) ?
C7 C8 . 1.511(4) ?
C7 C6 . 1.516(4) ?
C9 C10 . 1.512(3) ?
C15 C14 . 1.379(3) ?
C15 C16 . 1.386(3) ?
C16 C17 . 1.377(3) ?
C17 C12 . 1.393(3) ?
C18 C19 . 1.514(3) ?
C19 C24 . 1.394(3) ?
C19 C20 . 1.397(3) ?
C20 C21 . 1.384(3) ?
C21 C22 . 1.383(3) ?
C22 C23 . 1.378(3) ?
C23 C24 . 1.388(3) ?
C14 C13 . 1.392(3) ?
C13 C12 . 1.406(3) ?
C12 C11 . 1.497(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Zn1 N2 . . 119.35(7) ?
O1 Zn1 N4 . . 133.74(7) ?
N2 Zn1 N4 . . 106.77(8) ?
O1 Zn1 N1 . . 94.05(6) ?
N2 Zn1 N1 . . 96.32(7) ?
N4 Zn1 N1 . . 83.86(6) ?
O1 Zn1 N3 . . 90.15(6) ?
N2 Zn1 N3 . . 82.92(7) ?
N4 Zn1 N3 . . 92.13(7) ?
N1 Zn1 N3 . . 175.53(6) ?
N1 C1 C2 . . 116.12(18) ?
C10 N1 C1 . . 110.21(16) ?
C10 N1 C18 . . 111.09(15) ?
C1 N1 C18 . . 109.28(15) ?
C10 N1 Zn1 . . 102.15(11) ?
C1 N1 Zn1 . . 114.94(13) ?
C18 N1 Zn1 . . 109.02(11) ?
C13 O1 Zn1 . . 117.78(11) ?
O7 S1 O5 . . 114.56(16) ?
O7 S1 O6 . . 112.44(18) ?
O5 S1 O6 . . 116.01(15) ?
O7 S1 C25 . . 103.57(16) ?
O5 S1 C25 . . 105.83(16) ?
O6 S1 C25 . . 102.54(15) ?
N2 C3 C2 . . 111.4(2) ?
C5 N3 C6 . . 110.61(18) ?
C5 N3 C11 . . 109.29(18) ?
C6 N3 C11 . . 108.22(18) ?
C5 N3 Zn1 . . 102.71(13) ?
C6 N3 Zn1 . . 117.94(14) ?
C11 N3 Zn1 . . 107.78(12) ?
C3 C2 C1 . . 116.6(2) ?
C3 N2 C4 . . 113.89(19) ?
C3 N2 Zn1 . . 115.01(14) ?
C4 N2 Zn1 . . 108.09(14) ?
N2 C4 C5 . . 109.1(2) ?
C8 N4 C9 . . 113.20(18) ?
C8 N4 Zn1 . . 117.93(15) ?
C9 N4 Zn1 . . 106.67(12) ?
N3 C5 C4 . . 111.94(18) ?
C8 C7 C6 . . 115.1(2) ?
N3 C6 C7 . . 115.49(19) ?
N4 C9 C10 . . 108.33(17) ?
N4 C8 C7 . . 111.5(2) ?
C14 C15 C16 . . 120.1(2) ?
O2 C16 C17 . . 122.7(2) ?
O2 C16 C15 . . 117.8(2) ?
C17 C16 C15 . . 119.5(2) ?
C16 C17 C12 . . 121.10(19) ?
N1 C18 C19 . . 116.80(15) ?
C24 C19 C20 . . 117.90(18) ?
C24 C19 C18 . . 120.08(17) ?
C20 C19 C18 . . 122.00(18) ?
C21 C20 C19 . . 121.44(19) ?
O4 C21 C22 . . 117.82(18) ?
O4 C21 C20 . . 122.60(19) ?
C22 C21 C20 . . 119.58(19) ?
C23 C22 C21 . . 120.00(19) ?
C22 C23 C24 . . 120.39(19) ?
O3 C24 C23 . . 122.31(19) ?
O3 C24 C19 . . 116.99(18) ?
C23 C24 C19 . . 120.68(19) ?
F3 C25 F1 . . 108.4(3) ?
F3 C25 F2 . . 107.1(3) ?
F1 C25 F2 . . 106.7(3) ?
F3 C25 S1 . . 112.6(3) ?
F1 C25 S1 . . 111.75(19) ?
F2 C25 S1 . . 110.0(2) ?
C15 C14 C13 . . 121.35(19) ?
O1 C13 C14 . . 120.92(17) ?
O1 C13 C12 . . 120.61(19) ?
C14 C13 C12 . . 118.40(19) ?
C17 C12 C13 . . 119.55(19) ?
C17 C12 C11 . . 121.90(18) ?
C13 C12 C11 . . 118.50(18) ?
N3 C11 C12 . . 112.20(17) ?
N1 C10 C9 . . 111.23(16) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 N1 C10 . . . . 76.6(2) ?
C2 C1 N1 C18 . . . . -161.09(19) ?
C2 C1 N1 Zn1 . . . . -38.2(2) ?
N2 C3 C2 C1 . . . . -79.3(3) ?
N1 C1 C2 C3 . . . . 66.6(3) ?
C2 C3 N2 C4 . . . . -172.95(19) ?
C2 C3 N2 Zn1 . . . . 61.5(2) ?
C3 N2 C4 C5 . . . . -176.8(2) ?
Zn1 N2 C4 C5 . . . . -47.7(2) ?
C6 N3 C5 C4 . . . . -161.1(2) ?
C11 N3 C5 C4 . . . . 79.9(2) ?
Zn1 N3 C5 C4 . . . . -34.4(2) ?
N2 C4 C5 N3 . . . . 57.1(3) ?
C5 N3 C6 C7 . . . . 79.3(3) ?
C11 N3 C6 C7 . . . . -161.0(2) ?
Zn1 N3 C6 C7 . . . . -38.4(3) ?
C8 C7 C6 N3 . . . . 66.2(3) ?
C8 N4 C9 C10 . . . . -178.53(18) ?
Zn1 N4 C9 C10 . . . . -47.21(19) ?
C9 N4 C8 C7 . . . . -171.71(19) ?
Zn1 N4 C8 C7 . . . . 62.8(2) ?
C6 C7 C8 N4 . . . . -79.2(3) ?
C14 C15 C16 O2 . . . . -179.8(2) ?
C14 C15 C16 C17 . . . . 0.7(3) ?
O2 C16 C17 C12 . . . . -179.98(19) ?
C15 C16 C17 C12 . . . . -0.5(3) ?
C10 N1 C18 C19 . . . . 51.6(2) ?
C1 N1 C18 C19 . . . . -70.2(2) ?
Zn1 N1 C18 C19 . . . . 163.45(13) ?
N1 C18 C19 C24 . . . . -100.6(2) ?
N1 C18 C19 C20 . . . . 81.1(2) ?
C24 C19 C20 C21 . . . . 0.1(3) ?
C18 C19 C20 C21 . . . . 178.52(18) ?
C19 C20 C21 O4 . . . . 179.3(2) ?
C19 C20 C21 C22 . . . . -0.2(3) ?
O4 C21 C22 C23 . . . . -179.4(2) ?
C20 C21 C22 C23 . . . . 0.2(3) ?
C21 C22 C23 C24 . . . . 0.0(3) ?
C22 C23 C24 O3 . . . . -178.5(2) ?
C22 C23 C24 C19 . . . . -0.2(3) ?
C20 C19 C24 O3 . . . . 178.55(19) ?
C18 C19 C24 O3 . . . . 0.1(3) ?
C20 C19 C24 C23 . . . . 0.1(3) ?
C18 C19 C24 C23 . . . . -178.36(18) ?
O7 S1 C25 F3 . . . . 173.5(3) ?
O5 S1 C25 F3 . . . . 52.6(3) ?
O6 S1 C25 F3 . . . . -69.4(3) ?
O7 S1 C25 F1 . . . . -64.2(3) ?
O5 S1 C25 F1 . . . . 174.9(2) ?
O6 S1 C25 F1 . . . . 52.9(3) ?
O7 S1 C25 F2 . . . . 54.1(3) ?
O5 S1 C25 F2 . . . . -66.8(3) ?
O6 S1 C25 F2 . . . . 171.2(3) ?
C16 C15 C14 C13 . . . . 0.4(3) ?
Zn1 O1 C13 C14 . . . . 123.21(17) ?
Zn1 O1 C13 C12 . . . . -59.8(2) ?
C15 C14 C13 O1 . . . . 175.58(19) ?
C15 C14 C13 C12 . . . . -1.5(3) ?
C16 C17 C12 C13 . . . . -0.7(3) ?
C16 C17 C12 C11 . . . . -178.31(19) ?
O1 C13 C12 C17 . . . . -175.42(17) ?
C14 C13 C12 C17 . . . . 1.7(3) ?
O1 C13 C12 C11 . . . . 2.2(3) ?
C14 C13 C12 C11 . . . . 179.36(18) ?
C5 N3 C11 C12 . . . . -169.60(18) ?
C6 N3 C11 C12 . . . . 69.9(2) ?
Zn1 N3 C11 C12 . . . . -58.7(2) ?
C17 C12 C11 N3 . . . . -118.6(2) ?
C13 C12 C11 N3 . . . . 63.8(2) ?
C1 N1 C10 C9 . . . . -161.21(17) ?
C18 N1 C10 C9 . . . . 77.5(2) ?
Zn1 N1 C10 C9 . . . . -38.60(18) ?
N4 C9 C10 N1 . . . . 60.5(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 S1 . 0.83 2.89 3.4728(17) 128.8 ?
O3 H3 O6 . 0.83 1.96 2.724(3) 152.5 ?
O2 H5 O4 1_545 0.78(4) 2.00(4) 2.744(3) 160.(4) ?
N2 H2 S1 1_655 0.83(3) 2.89(3) 3.714(2) 171.(2) ?
N2 H2 O7 1_655 0.83(3) 2.40(3) 3.190(3) 160.(2) ?
O4 H4 O1 2_655 0.85 1.79 2.622(2) 164.0 ?
N4 H1 O7 1_655 0.86(3) 2.20(3) 3.036(3) 164.(2) ?
C9 H9AB O3 . 0.97 2.4 3.143(3) 133.5 ?
C11 H11A F2 3_656 0.97 2.54 3.474(3) 162.3 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol, diethyl ether'
_chemical_properties_physical    Hygroscopic
