# 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 
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data_sad2_xp_a
_database_code_depnum_ccdc_archive 'CCDC 1814568'
_audit_update_record             
;
2018-01-03 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2 O5 Zn'
_chemical_formula_sum            'C23 H17 N2 O5 Zn'
_chemical_formula_weight         466.75
_chemical_melting_point          ?
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                   14.9534(6)
_cell_length_b                   23.9949(9)
_cell_length_c                   15.9759(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.674(2)
_cell_angle_gamma                90
_cell_volume                     5289.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    93294
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.9675
_cell_measurement_theta_min      3.681
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.9178.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51821
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.912
_diffrn_reflns_theta_min         3.684
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon 100'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4792
_reflns_number_total             5417
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+3.9901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C8 \\sim C10 \\sim C12 \\sim C13 \\sim C11 \\sim C9: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
3.a Riding coordinates:
 N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C17(H17), C4(H4), C16(H16), C6(H6), C23(H23), C22(H22),
 C10(H10), C12(H12), C15(H15), C18(H18), C9(H9), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Zn1 Zn 0.07965(2) 0.51134(2) 0.36401(2) 0.02649(8) Uani 1 1 d . . . . .
O5 O 0.47556(8) 0.93468(4) 0.14240(7) 0.0275(2) Uani 1 1 d . . . . .
O4 O 0.32733(9) 0.93331(5) 0.13932(8) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.03842(10) 0.55360(5) 0.14315(7) 0.0369(3) Uani 1 1 d . . . . .
O3 O 0.41041(9) 0.67307(5) 0.13131(8) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.13562(10) 0.55252(5) 0.29047(8) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.16743(10) 0.53250(5) 0.49319(8) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.41088(11) 0.51513(6) 0.81096(9) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.3867 0.4844 0.7841 0.041 Uiso 1 1 d R . . . .
C2 C 0.40343(10) 0.84611(6) 0.13993(9) 0.0209(3) Uani 1 1 d . . . . .
C1 C 0.40128(11) 0.90814(6) 0.14147(9) 0.0227(3) Uani 1 1 d . . . . .
C5 C 0.48108(11) 0.76006(6) 0.12789(11) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.5324 0.7412 0.1214 0.032 Uiso 1 1 calc R . . . .
C3 C 0.48062(10) 0.81768(6) 0.13121(10) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.5323 0.8376 0.1276 0.029 Uiso 1 1 calc R . . . .
C7 C 0.40421(11) 0.73079(6) 0.13434(10) 0.0262(3) Uani 1 1 d . . . . .
C17 C 0.18379(12) 0.56058(7) 0.64208(10) 0.0290(3) Uani 1 1 d . . . . .
H17 H 0.1546 0.5730 0.6806 0.035 Uiso 1 1 calc R . . . .
C4 C 0.32693(10) 0.81586(7) 0.14520(10) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.2751 0.8346 0.1508 0.032 Uiso 1 1 calc R . . . .
C16 C 0.12875(12) 0.55087(6) 0.55119(10) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.0623 0.5573 0.5295 0.034 Uiso 1 1 calc R . . . .
C13 C 0.19553(14) 0.59056(7) 0.18793(10) 0.0361(4) Uani 1 1 d . U . . .
C8 C 0.33964(14) 0.64406(7) 0.15084(11) 0.0353(4) Uani 1 1 d . U . . .
C19 C 0.28312(13) 0.55156(7) 0.67505(10) 0.0327(4) Uani 1 1 d . . . . .
C6 C 0.32618(11) 0.75826(7) 0.14227(11) 0.0296(3) Uani 1 1 d . . . . .
H6 H 0.2743 0.7383 0.1455 0.035 Uiso 1 1 calc R . . . .
C14 C 0.11711(14) 0.56319(6) 0.20857(10) 0.0342(4) Uani 1 1 d . . . . .
C23 C 0.45580(12) 0.55049(7) 0.96567(10) 0.0305(3) Uani 1 1 d . . . . .
H23 H 0.4265 0.5845 0.9436 0.037 Uiso 1 1 calc R . . . .
C21 C 0.45287(11) 0.50797(7) 0.90555(11) 0.0287(3) Uani 1 1 d . . . . .
C22 C 0.49758(12) 0.45772(7) 0.94114(11) 0.0320(4) Uani 1 1 d . . . . .
H22 H 0.4964 0.4289 0.9018 0.038 Uiso 1 1 calc R . . . .
C10 C 0.26007(14) 0.62357(8) 0.08004(11) 0.0399(4) Uani 1 1 d . U . . .
H10 H 0.2553 0.6272 0.0205 0.048 Uiso 1 1 calc R . . . .
C12 C 0.18756(14) 0.59760(7) 0.09892(11) 0.0390(4) Uani 1 1 d . U . . .
H12 H 0.1327 0.5847 0.0515 0.047 Uiso 1 1 calc R . . . .
C15 C 0.26349(13) 0.52384(8) 0.52490(11) 0.0357(4) Uani 1 1 d . . . . .
H15 H 0.2909 0.5110 0.4852 0.043 Uiso 1 1 calc R . . . .
C18 C 0.32324(14) 0.53335(9) 0.61460(11) 0.0401(4) Uani 1 1 d . . . . .
H18 H 0.3897 0.5276 0.6342 0.048 Uiso 1 1 calc R . . . .
C9 C 0.35165(15) 0.63603(8) 0.24015(12) 0.0460(5) Uani 1 1 d . U . . .
H9 H 0.4072 0.6487 0.2871 0.055 Uiso 1 1 calc R . . . .
C11 C 0.28007(16) 0.60903(8) 0.25847(11) 0.0457(5) Uani 1 1 d . U . . .
H11 H 0.2879 0.6029 0.3184 0.055 Uiso 1 1 calc R . . . .
C20 C 0.34380(13) 0.56086(9) 0.77444(11) 0.0404(4) Uani 1 1 d . . . . .
H20A H 0.3797 0.5954 0.7818 0.048 Uiso 1 1 calc R . . . .
H20B H 0.3018 0.5641 0.8077 0.048 Uiso 1 1 calc R . . . .


_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 O5 2.0027(11) 4_545 ?
Zn1 O4 2.3452(12) 4_545 ?
Zn1 O2 2.0006(12) 2 ?
Zn1 O1 1.9532(12) . ?
Zn1 N1 2.0375(13) . ?
O5 Zn1 2.0026(11) 4 ?
O5 C1 1.2755(19) . ?
O4 Zn1 2.3452(12) 4 ?
O4 C1 1.2487(19) . ?
O2 Zn1 2.0007(12) 2 ?
O2 C14 1.258(2) . ?
O3 C7 1.3903(19) . ?
O3 C8 1.399(2) . ?
O1 C14 1.255(2) . ?
N1 C16 1.342(2) . ?
N1 C15 1.342(2) . ?
N2 H2 0.8601 . ?
N2 C21 1.406(2) . ?
N2 C20 1.449(2) . ?
C2 C1 1.489(2) . ?
C2 C3 1.393(2) . ?
C2 C4 1.385(2) . ?
C1 Zn1 2.4979(15) 4 ?
C5 H5 0.9300 . ?
C5 C3 1.384(2) . ?
C5 C7 1.384(2) . ?
C3 H3 0.9300 . ?
C7 C6 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.385(2) . ?
C17 C19 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C6 1.383(2) . ?
C16 H16 0.9300 . ?
C13 C14 1.488(3) . ?
C13 C12 1.391(2) . ?
C13 C11 1.402(2) . ?
C8 C10 1.378(2) . ?
C8 C9 1.381(3) . ?
C19 C18 1.389(2) . ?
C19 C20 1.511(2) . ?
C6 H6 0.9300 . ?
C23 H23 0.9300 . ?
C23 C21 1.390(2) . ?
C23 C22 1.393(2) 5_667 ?
C21 C22 1.390(2) . ?
C22 C23 1.393(2) 5_667 ?
C22 H22 0.9300 . ?
C10 H10 0.9300 . ?
C10 C12 1.381(3) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C15 C18 1.385(2) . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
C9 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
O5 Zn1 O4 60.13(4) 4_545 4_545 ?
O5 Zn1 N1 111.88(5) 4_545 . ?
O2 Zn1 O5 97.20(5) 2 4_545 ?
O2 Zn1 O4 157.13(5) 2 4_545 ?
O2 Zn1 N1 98.13(5) 2 . ?
O1 Zn1 O5 134.24(5) . 4_545 ?
O1 Zn1 O4 89.70(5) . 4_545 ?
O1 Zn1 O2 106.41(6) . 2 ?
O1 Zn1 N1 103.01(6) . . ?
N1 Zn1 O4 93.77(5) . 4_545 ?
C1 O5 Zn1 96.77(9) . 4 ?
C1 O4 Zn1 81.95(9) . 4 ?
C14 O2 Zn1 131.50(11) . 2 ?
C7 O3 C8 114.94(14) . . ?
C14 O1 Zn1 139.20(12) . . ?
C16 N1 Zn1 120.03(11) . . ?
C16 N1 C15 118.27(13) . . ?
C15 N1 Zn1 121.43(11) . . ?
C21 N2 H2 111.0 . . ?
C21 N2 C20 118.58(13) . . ?
C20 N2 H2 110.9 . . ?
C3 C2 C1 121.00(13) . . ?
C4 C2 C1 119.96(14) . . ?
C4 C2 C3 119.02(14) . . ?
O5 C1 Zn1 52.76(7) . 4 ?
O5 C1 C2 118.35(13) . . ?
O4 C1 Zn1 68.38(9) . 4 ?
O4 C1 O5 121.12(14) . . ?
O4 C1 C2 120.50(14) . . ?
C2 C1 Zn1 170.65(11) . 4 ?
C3 C5 H5 120.4 . . ?
C3 C5 C7 119.18(14) . . ?
C7 C5 H5 120.4 . . ?
C2 C3 H3 119.7 . . ?
C5 C3 C2 120.64(13) . . ?
C5 C3 H3 119.7 . . ?
C5 C7 O3 115.75(14) . . ?
C5 C7 C6 121.16(14) . . ?
C6 C7 O3 123.09(14) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C19 119.21(15) . . ?
C19 C17 H17 120.4 . . ?
C2 C4 H4 119.4 . . ?
C6 C4 C2 121.20(14) . . ?
C6 C4 H4 119.4 . . ?
N1 C16 C17 122.62(15) . . ?
N1 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C12 C13 C14 121.07(15) . . ?
C12 C13 C11 118.60(17) . . ?
C11 C13 C14 120.32(15) . . ?
C10 C8 O3 118.85(15) . . ?
C10 C8 C9 121.70(17) . . ?
C9 C8 O3 119.45(15) . . ?
C17 C19 C18 118.09(15) . . ?
C17 C19 C20 119.79(15) . . ?
C18 C19 C20 122.11(16) . . ?
C7 C6 H6 120.6 . . ?
C4 C6 C7 118.79(14) . . ?
C4 C6 H6 120.6 . . ?
O2 C14 C13 117.48(14) . . ?
O1 C14 O2 126.06(17) . . ?
O1 C14 C13 116.45(15) . . ?
C21 C23 H23 119.9 . . ?
C21 C23 C22 120.28(16) . 5_667 ?
C22 C23 H23 119.9 5_667 . ?
C23 C21 N2 122.36(15) . . ?
C22 C21 N2 119.40(15) . . ?
C22 C21 C23 118.16(15) . . ?
C23 C22 H22 119.2 5_667 . ?
C21 C22 C23 121.57(16) . 5_667 ?
C21 C22 H22 119.2 . . ?
C8 C10 H10 120.5 . . ?
C8 C10 C12 118.94(16) . . ?
C12 C10 H10 120.5 . . ?
C13 C12 H12 119.6 . . ?
C10 C12 C13 120.87(16) . . ?
C10 C12 H12 119.6 . . ?
N1 C15 H15 118.8 . . ?
N1 C15 C18 122.33(16) . . ?
C18 C15 H15 118.8 . . ?
C19 C18 H18 120.3 . . ?
C15 C18 C19 119.47(17) . . ?
C15 C18 H18 120.3 . . ?
C8 C9 H9 120.5 . . ?
C11 C9 C8 118.91(16) . . ?
C11 C9 H9 120.5 . . ?
C13 C11 H11 119.6 . . ?
C9 C11 C13 120.81(16) . . ?
C9 C11 H11 119.6 . . ?
N2 C20 C19 110.69(14) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?

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
Zn1 O5 C1 O4 -1.47(14) 4 . . . ?
Zn1 O5 C1 C2 176.54(10) 4 . . . ?
Zn1 O4 C1 O5 1.26(12) 4 . . . ?
Zn1 O4 C1 C2 -176.71(12) 4 . . . ?
Zn1 O2 C14 O1 -8.5(3) 2 . . . ?
Zn1 O2 C14 C13 172.58(12) 2 . . . ?
Zn1 O1 C14 O2 10.8(3) . . . . ?
Zn1 O1 C14 C13 -170.26(14) . . . . ?
Zn1 N1 C16 C17 173.42(12) . . . . ?
Zn1 N1 C15 C18 -174.22(15) . . . . ?
O3 C7 C6 C4 179.66(14) . . . . ?
O3 C8 C10 C12 -176.48(17) . . . . ?
O3 C8 C9 C11 177.91(18) . . . . ?
N1 C15 C18 C19 1.2(3) . . . . ?
N2 C21 C22 C23 176.94(16) . . . 5_667 ?
C2 C4 C6 C7 0.3(2) . . . . ?
C1 C2 C3 C5 -178.61(13) . . . . ?
C1 C2 C4 C6 178.81(14) . . . . ?
C5 C7 C6 C4 -1.1(2) . . . . ?
C3 C2 C1 O5 -5.88(19) . . . . ?
C3 C2 C1 O4 172.14(13) . . . . ?
C3 C2 C4 C6 0.2(2) . . . . ?
C3 C5 C7 O3 -179.42(13) . . . . ?
C3 C5 C7 C6 1.3(2) . . . . ?
C7 O3 C8 C10 99.62(19) . . . . ?
C7 O3 C8 C9 -81.2(2) . . . . ?
C7 C5 C3 C2 -0.7(2) . . . . ?
C17 C19 C18 C15 -1.2(3) . . . . ?
C17 C19 C20 N2 134.46(18) . . . . ?
C4 C2 C1 O5 175.56(13) . . . . ?
C4 C2 C1 O4 -6.4(2) . . . . ?
C4 C2 C3 C5 0.0(2) . . . . ?
C16 N1 C15 C18 -0.2(3) . . . . ?
C16 C17 C19 C18 0.4(3) . . . . ?
C16 C17 C19 C20 -178.76(17) . . . . ?
C8 O3 C7 C5 171.26(13) . . . . ?
C8 O3 C7 C6 -9.4(2) . . . . ?
C8 C10 C12 C13 -2.0(3) . . . . ?
C8 C9 C11 C13 -0.9(3) . . . . ?
C19 C17 C16 N1 0.6(3) . . . . ?
C14 C13 C12 C10 179.30(18) . . . . ?
C14 C13 C11 C9 -177.84(19) . . . . ?
C23 C21 C22 C23 0.1(3) . . . 5_667 ?
C21 N2 C20 C19 -161.94(17) . . . . ?
C22 C23 C21 N2 -176.83(16) 5_667 . . . ?
C22 C23 C21 C22 -0.1(3) 5_667 . . . ?
C10 C8 C9 C11 -3.0(3) . . . . ?
C12 C13 C14 O2 -9.5(3) . . . . ?
C12 C13 C14 O1 171.51(18) . . . . ?
C12 C13 C11 C9 3.2(3) . . . . ?
C15 N1 C16 C17 -0.7(2) . . . . ?
C18 C19 C20 N2 -44.7(3) . . . . ?
C9 C8 C10 C12 4.4(3) . . . . ?
C11 C13 C14 O2 171.60(18) . . . . ?
C11 C13 C14 O1 -7.4(3) . . . . ?
C11 C13 C12 C10 -1.7(3) . . . . ?
C20 N2 C21 C23 -19.1(3) . . . . ?
C20 N2 C21 C22 164.22(17) . . . . ?
C20 C19 C18 C15 177.91(19) . . . . ?

_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 -0.126 0.250 0.624 889.2 206.5 ?
2 0.643 0.750 0.893 889.2 206.5 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_TMU-21(RL2)_sq
_database_code_depnum_ccdc_archive 'CCDC 1814569'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 N2 O5 Zn, C3 H7 N O'
_chemical_formula_sum            'C28 H25 N3 O6 Zn'
_chemical_formula_weight         564.88

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'

_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                   14.6564(9)
_cell_length_b                   25.3323(10)
_cell_length_c                   15.9430(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.865(6)
_cell_angle_gamma                90
_cell_volume                     5567.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5490
_cell_measurement_theta_min      4.2190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44109
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_min         4.212
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPAD dectris PILATUS 200K'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  68.00   0.50   45.00    --   -0.30  38.00 150.00   52
  2  ω    -18.00  44.00   0.50   45.00    --   -0.30  38.00 -60.00  124
  3  ω     56.00  82.00   0.50   45.00    --   -0.30  38.00 -60.00   52
  4  ω     -9.00  21.00   0.50   45.00    --   -0.30  38.00  90.00   60
  5  ω     44.00  79.00   0.50   45.00    --   -0.30  38.00-150.00   70
  6  ω    -21.00  16.00   0.50   45.00    --   -0.30  38.00 -90.00   74
  7  ω    -24.00  89.00   0.50   45.00    --   -0.30  38.00  30.00  226
  8  ω     51.00  86.00   0.50   45.00    --   -0.30  19.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0231646000
_diffrn_orient_matrix_UB_12      -0.0134472000
_diffrn_orient_matrix_UB_13      -0.0407013000
_diffrn_orient_matrix_UB_21      0.0353460000
_diffrn_orient_matrix_UB_22      0.0098442000
_diffrn_orient_matrix_UB_23      -0.0172538000
_diffrn_orient_matrix_UB_31      0.0293631000
_diffrn_orient_matrix_UB_32      -0.0225063000
_diffrn_orient_matrix_UB_33      0.0167998000
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6003
_reflns_number_total             7876
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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    ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         7863
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+2.5694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C19(H19), C18(H18), C9(H9), C3(H3), C13(H13), C7(H7),
 C4(H4), C15(H15), C6(H6), C24(H24), C22(H22), C16(H16), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.07779(2) 0.50358(2) 0.36096(2) 0.04194(8) Uani 1 1 d . . . . .
O4 O 0.47058(10) 0.93016(5) 0.14045(9) 0.0497(3) Uani 1 1 d . . . . .
O2 O 0.04026(11) 0.54525(6) 0.14329(10) 0.0559(4) Uani 1 1 d . . . . .
O3 O 0.32541(12) 0.93087(5) 0.15011(11) 0.0597(4) Uani 1 1 d . . . . .
N1 N 0.16398(12) 0.52450(6) 0.48663(11) 0.0453(3) Uani 1 1 d . . . . .
O5 O 0.39806(11) 0.68345(5) 0.13402(11) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.13176(11) 0.54618(6) 0.28679(10) 0.0612(4) Uani 1 1 d . . . . .
C14 C 0.39617(14) 0.90602(7) 0.14529(11) 0.0409(4) Uani 1 1 d . . . . .
C2 C 0.18864(13) 0.59182(6) 0.18691(11) 0.0376(3) Uani 1 1 d . . . . .
C11 C 0.39622(13) 0.84730(6) 0.14379(11) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.11409(13) 0.55827(6) 0.20668(12) 0.0406(4) Uani 1 1 d . . . . .
N2 N 0.39100(16) 0.53079(8) 0.80530(14) 0.0658(5) Uani 1 1 d D . . . .
H2 H 0.355(2) 0.5031(8) 0.795(2) 0.079 Uiso 1 1 d D U . . .
C5 C 0.32657(14) 0.65377(7) 0.15223(14) 0.0463(4) Uani 1 1 d . . . . .
C8 C 0.39229(14) 0.73774(7) 0.13778(13) 0.0446(4) Uani 1 1 d . . . . .
C12 C 0.47173(14) 0.81933(7) 0.13104(14) 0.0487(4) Uani 1 1 d . . . . .
H12 H 0.523942 0.837582 0.124473 0.058 Uiso 1 1 calc R U . . .
C10 C 0.31882(14) 0.81921(7) 0.15353(14) 0.0493(4) Uani 1 1 d . . . . .
H10 H 0.267716 0.837500 0.162201 0.059 Uiso 1 1 calc R U . . .
C19 C 0.12643(14) 0.54829(9) 0.54271(13) 0.0513(4) Uani 1 1 d . . . . .
H19 H 0.060096 0.554957 0.523263 0.062 Uiso 1 1 calc R U . . .
C18 C 0.18178(15) 0.56323(9) 0.62770(14) 0.0550(5) Uani 1 1 d . . . . .
H18 H 0.152523 0.578942 0.664824 0.066 Uiso 1 1 calc R U . . .
C9 C 0.31638(14) 0.76475(7) 0.15058(15) 0.0514(5) Uani 1 1 d . . . . .
H9 H 0.264174 0.746492 0.157145 0.062 Uiso 1 1 calc R U . . .
C3 C 0.26592(15) 0.61198(9) 0.25551(13) 0.0543(5) Uani 1 1 d . . . . .
H3 H 0.271687 0.604462 0.314189 0.065 Uiso 1 1 calc R U . . .
C13 C 0.47086(15) 0.76482(8) 0.12790(15) 0.0530(5) Uani 1 1 d . . . . .
H13 H 0.521922 0.746452 0.119327 0.064 Uiso 1 1 calc R U . . .
C7 C 0.18215(17) 0.60286(10) 0.10019(13) 0.0633(6) Uani 1 1 d . . . . .
H7 H 0.130619 0.589461 0.053032 0.076 Uiso 1 1 calc R U . . .
C17 C 0.28028(15) 0.55497(9) 0.65782(15) 0.0559(5) Uani 1 1 d . . . . .
C4 C 0.33498(16) 0.64318(9) 0.23858(14) 0.0597(5) Uani 1 1 d . . . . .
H4 H 0.386588 0.656821 0.285394 0.072 Uiso 1 1 calc R U . . .
C15 C 0.25974(17) 0.51354(11) 0.51837(18) 0.0685(6) Uani 1 1 d . . . . .
H15 H 0.286976 0.495474 0.481888 0.082 Uiso 1 1 calc R U . . .
C6 C 0.25178(19) 0.63374(11) 0.08290(14) 0.0702(7) Uani 1 1 d . . . . .
H6 H 0.247510 0.640736 0.024420 0.084 Uiso 1 1 calc R U . . .
C25 C 0.52326(15) 0.50422(8) 1.04651(16) 0.0533(5) Uani 1 1 d . . . . .
C21 C 0.43720(14) 0.53971(10) 0.89631(15) 0.0564(5) Uani 1 1 d . . . . .
C20 C 0.34227(18) 0.57357(10) 0.74920(17) 0.0689(6) Uani 1 1 d . . . . .
H20A H 0.390057 0.598463 0.743394 0.083 Uiso 1 1 calc R U . . .
H20B H 0.301758 0.591826 0.776955 0.083 Uiso 1 1 calc R U . . .
C24 C 0.52754(19) 0.55640(10) 1.07978(17) 0.0683(6) Uani 1 1 d . . . . .
H24 H 0.555290 0.562526 1.140723 0.082 Uiso 1 1 calc R U . . .
C22 C 0.44768(18) 0.59007(10) 0.93203(18) 0.0678(6) Uani 1 1 d . . . . .
H22 H 0.425386 0.619014 0.894792 0.081 Uiso 1 1 calc R U . . .
C16 C 0.31861(17) 0.52796(13) 0.60233(19) 0.0792(8) Uani 1 1 d . . . . .
H16 H 0.384272 0.519542 0.621784 0.095 Uiso 1 1 calc R U . . .
C23 C 0.4915(2) 0.59757(11) 1.0236(2) 0.0772(7) Uani 1 1 d . . . . .
H23 H 0.496252 0.631545 1.046833 0.093 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 O1 1.9554(13) . ?
Zn1 O4 1.9879(14) 4_545 ?
Zn1 O2 2.0081(13) 2 ?
Zn1 N1 2.0422(17) . ?
Zn1 O3 2.3679(14) 4_545 ?
Zn1 C14 2.5081(17) 4_545 ?
O4 C14 1.275(2) . ?
O2 C1 1.248(2) . ?
O3 C14 1.238(2) . ?
N1 C19 1.342(2) . ?
N1 C15 1.349(3) . ?
O5 C8 1.381(2) . ?
O5 C5 1.398(2) . ?
O1 C1 1.252(2) . ?
C14 C11 1.487(2) . ?
C2 C3 1.378(2) . ?
C2 C7 1.382(3) . ?
C2 C1 1.500(2) . ?
C11 C12 1.386(3) . ?
C11 C10 1.392(2) . ?
N2 C21 1.395(3) . ?
N2 C20 1.432(3) . ?
N2 H2 0.857(17) . ?
C5 C6 1.363(3) . ?
C5 C4 1.366(3) . ?
C8 C9 1.379(3) . ?
C8 C13 1.394(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C10 C9 1.381(3) . ?
C10 H10 0.9300 . ?
C19 C18 1.375(3) . ?
C19 H19 0.9300 . ?
C18 C17 1.374(3) . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C7 C6 1.386(3) . ?
C7 H7 0.9300 . ?
C17 C16 1.380(3) . ?
C17 C20 1.507(3) . ?
C4 H4 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C25 C24 1.418(3) . ?
C25 C25 1.422(5) 5_667 ?
C25 C21 1.430(3) 5_667 ?
C21 C22 1.384(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C24 C23 1.359(4) . ?
C24 H24 0.9300 . ?
C22 C23 1.394(4) . ?
C22 H22 0.9300 . ?
C16 H16 0.9300 . ?
C23 H23 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
O1 Zn1 O4 136.50(7) . 4_545 ?
O1 Zn1 O2 102.15(6) . 2 ?
O4 Zn1 O2 101.04(6) 4_545 2 ?
O1 Zn1 N1 101.98(6) . . ?
O4 Zn1 N1 110.68(6) 4_545 . ?
O2 Zn1 N1 97.78(6) 2 . ?
O1 Zn1 O3 90.48(6) . 4_545 ?
O4 Zn1 O3 59.45(5) 4_545 4_545 ?
O2 Zn1 O3 159.64(6) 2 4_545 ?
N1 Zn1 O3 95.07(6) . 4_545 ?
O1 Zn1 C14 114.93(7) . 4_545 ?
O4 Zn1 C14 30.23(6) 4_545 4_545 ?
O2 Zn1 C14 131.12(6) 2 4_545 ?
N1 Zn1 C14 104.06(6) . 4_545 ?
O3 Zn1 C14 29.23(5) 4_545 4_545 ?
C14 O4 Zn1 98.07(12) . 4 ?
C1 O2 Zn1 131.78(12) . 2 ?
C14 O3 Zn1 81.67(11) . 4 ?
C19 N1 C15 116.91(18) . . ?
C19 N1 Zn1 120.88(13) . . ?
C15 N1 Zn1 122.17(14) . . ?
C8 O5 C5 117.74(15) . . ?
C1 O1 Zn1 139.99(14) . . ?
O3 C14 O4 120.76(17) . . ?
O3 C14 C11 120.97(16) . . ?
O4 C14 C11 118.26(17) . . ?
O3 C14 Zn1 69.10(10) . 4 ?
O4 C14 Zn1 51.70(9) . 4 ?
C11 C14 Zn1 169.67(13) . 4 ?
C3 C2 C7 118.54(16) . . ?
C3 C2 C1 120.29(15) . . ?
C7 C2 C1 121.17(16) . . ?
C12 C11 C10 118.47(16) . . ?
C12 C11 C14 121.23(16) . . ?
C10 C11 C14 120.30(17) . . ?
O2 C1 O1 125.68(17) . . ?
O2 C1 C2 118.20(15) . . ?
O1 C1 C2 116.11(16) . . ?
C21 N2 C20 119.3(2) . . ?
C21 N2 H2 113(2) . . ?
C20 N2 H2 111(2) . . ?
C6 C5 C4 121.09(17) . . ?
C6 C5 O5 119.00(18) . . ?
C4 C5 O5 119.84(18) . . ?
C9 C8 O5 124.41(16) . . ?
C9 C8 C13 120.76(17) . . ?
O5 C8 C13 114.84(17) . . ?
C13 C12 C11 121.22(16) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C9 C10 C11 121.31(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
N1 C19 C18 122.83(18) . . ?
N1 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C17 C18 C19 120.03(18) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C8 C9 C10 119.21(16) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C2 C3 C4 121.09(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C12 C13 C8 119.03(18) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C2 C7 C6 120.54(18) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C18 C17 C16 117.4(2) . . ?
C18 C17 C20 120.46(19) . . ?
C16 C17 C20 122.1(2) . . ?
C5 C4 C3 119.21(18) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C15 C16 122.68(19) . . ?
N1 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C5 C6 C7 119.51(18) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C24 C25 C25 118.3(3) . 5_667 ?
C24 C25 C21 122.0(2) . 5_667 ?
C25 C25 C21 119.6(2) 5_667 5_667 ?
C22 C21 N2 121.6(2) . . ?
C22 C21 C25 119.4(2) . 5_667 ?
N2 C21 C25 119.0(2) . 5_667 ?
N2 C20 C17 112.1(2) . . ?
N2 C20 H20A 109.2 . . ?
C17 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C17 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?

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
Zn1 O3 C14 O4 1.78(16) 4 . . . ?
Zn1 O3 C14 C11 -177.43(15) 4 . . . ?
Zn1 O4 C14 O3 -2.12(19) 4 . . . ?
Zn1 O4 C14 C11 177.11(12) 4 . . . ?
O3 C14 C11 C12 174.64(18) . . . . ?
O4 C14 C11 C12 -4.6(2) . . . . ?
Zn1 C14 C11 C12 8.2(8) 4 . . . ?
O3 C14 C11 C10 -4.1(3) . . . . ?
O4 C14 C11 C10 176.68(16) . . . . ?
Zn1 C14 C11 C10 -170.6(6) 4 . . . ?
Zn1 O2 C1 O1 1.5(3) 2 . . . ?
Zn1 O2 C1 C2 -177.76(12) 2 . . . ?
Zn1 O1 C1 O2 4.7(3) . . . . ?
Zn1 O1 C1 C2 -176.04(15) . . . . ?
C3 C2 C1 O2 172.87(18) . . . . ?
C7 C2 C1 O2 -7.7(3) . . . . ?
C3 C2 C1 O1 -6.5(3) . . . . ?
C7 C2 C1 O1 173.0(2) . . . . ?
C8 O5 C5 C6 100.1(2) . . . . ?
C8 O5 C5 C4 -83.0(2) . . . . ?
C5 O5 C8 C9 -5.9(3) . . . . ?
C5 O5 C8 C13 173.79(18) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C14 C11 C12 C13 -178.71(18) . . . . ?
C12 C11 C10 C9 -0.1(3) . . . . ?
C14 C11 C10 C9 178.69(18) . . . . ?
C15 N1 C19 C18 2.6(3) . . . . ?
Zn1 N1 C19 C18 -179.73(17) . . . . ?
N1 C19 C18 C17 1.4(4) . . . . ?
O5 C8 C9 C10 179.73(19) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C11 C10 C9 C8 0.0(3) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 C4 -179.65(19) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
O5 C8 C13 C12 -179.79(18) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 -179.7(2) . . . . ?
C19 C18 C17 C16 -4.8(4) . . . . ?
C19 C18 C17 C20 177.0(2) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
O5 C5 C4 C3 -177.3(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C19 N1 C15 C16 -3.2(4) . . . . ?
Zn1 N1 C15 C16 179.2(2) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
O5 C5 C6 C7 178.0(2) . . . . ?
C2 C7 C6 C5 -0.7(4) . . . . ?
C20 N2 C21 C22 -8.2(3) . . . . ?
C20 N2 C21 C25 173.4(2) . . . 5_667 ?
C21 N2 C20 C17 -168.6(2) . . . . ?
C18 C17 C20 N2 118.8(3) . . . . ?
C16 C17 C20 N2 -59.3(3) . . . . ?
C25 C25 C24 C23 -2.6(4) 5_667 . . . ?
C21 C25 C24 C23 178.3(2) 5_667 . . . ?
N2 C21 C22 C23 178.0(2) . . . . ?
C25 C21 C22 C23 -3.6(3) 5_667 . . . ?
N1 C15 C16 C17 -0.2(5) . . . . ?
C18 C17 C16 C15 4.2(4) . . . . ?
C20 C17 C16 C15 -177.6(3) . . . . ?
C25 C24 C23 C22 1.2(4) . . . . ?
C21 C22 C23 C24 2.0(4) . . . . ?

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.057





