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The crystal structure of tris­[dimethyl 5-({1-[(pyridin-2-yl-κN)carbamoyl-κO]eth­yl}carbamo­yl)benzene-1,3-di­carboxyl­ate]zinc(II) dinitrate aceto­nitrile tri­solvate, [Zn(C19H19N3O6)3](NO3)2·3CH3CN or [Zn(L)3](NO3)2·3CH3CN, (1), has been determined by single-crystal X-ray diffraction. The neutral ligand L coordinates to the Zn2+ cation in a bidentate fashion via the pyridine N atom and an amide O atom, forming a six-membered chelate ring. The Λ-helical chirality of the Zn2+ coordination sphere is induced by pendant L-alanine residues through stacking inter­actions between the arene groups of two coordinated ligands, assisted by a hydrogen bond between amide groups bonded to the stacked arene rings. The third ligand is coordinated to the Zn2+ cation by the same six-membered chelate ring, but in the opposite direction with respect to the analogous chelate rings of the first two coordinated ligands. Besides ionic inter­actions between [ZnL3]2+ com­plexes and NO3 anions, several types of hydrogen bonds and inter­molecular stacking inter­actions contribute to the stability of the solid-state phase.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621006471/ef3020sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621006471/ef3020Isup2.hkl
Contains datablock I

CCDC reference: 2091352

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Tris[dimethyl 5-({1-[(pyridin-2-yl-κN)carbamoyl-κO]ethyl}carbamoyl)benzene-1,3-dicarboxylate]zinc(II) dinitrate acetonitrile trisolvate top
Crystal data top
[Zn(C19H19N3O6)3](NO3)2·3C2H3NF(000) = 1528
Mr = 1468.66Dx = 1.409 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 10.5897 (2) ÅCell parameters from 8319 reflections
b = 22.8595 (5) Åθ = 3.6–74.5°
c = 14.3102 (3) ŵ = 1.25 mm1
β = 92.524 (2)°T = 136 K
V = 3460.78 (12) Å3Prism, colourless
Z = 20.2 × 0.15 × 0.1 mm
Data collection top
Agilent Xcalibur Nova
diffractometer with a Ruby detector
10880 independent reflections
Radiation source: sealed X-ray tube10178 reflections with I > 2σ(I)
Detector resolution: 10.4323 pixels mm-1Rint = 0.038
ω scansθmax = 76.5°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 138
Tmin = 0.658, Tmax = 1.000k = 2528
19332 measured reflectionsl = 1617
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.077P)2 + 1.8689P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
10880 reflectionsΔρmax = 0.86 e Å3
955 parametersΔρmin = 0.66 e Å3
1 restraintAbsolute structure: Flack x determined using 3017 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
Special details top

Geometry. 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.

Refinement. The data were processed with the CrysalisPRO program (Agilent, 2014) for unit cell determination and data reduction. The structure was solved by direct methods using the SHELXT program (Sheldrick, 2015a) and refined against F2 on all data by a full-matrix least squares procedure with the SHELXL program (Sheldrick, 2015b). All non-H atoms were refined using anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.74871 (5)0.12080 (3)0.09775 (4)0.02888 (16)
N110.6173 (4)0.1615 (2)0.0009 (3)0.0303 (8)
C110.6131 (5)0.1429 (3)0.0882 (4)0.0409 (12)
H110.6730850.1157350.1056950.049*
C210.5252 (5)0.1617 (3)0.1548 (4)0.0458 (14)
H210.5266150.1480330.2159890.055*
C310.4339 (5)0.2017 (3)0.1292 (4)0.0433 (13)
H310.3717450.2143300.1724810.052*
C410.4371 (5)0.2223 (3)0.0387 (4)0.0388 (12)
H410.3784110.2497260.0201410.047*
C510.5308 (4)0.2010 (2)0.0250 (3)0.0303 (10)
N210.5299 (4)0.2225 (2)0.1159 (3)0.0337 (9)
H21N0.466 (6)0.247 (3)0.128 (5)0.034 (16)*
C610.6249 (5)0.2236 (2)0.1824 (4)0.0311 (10)
O110.7272 (3)0.19862 (17)0.1774 (2)0.0314 (7)
C710.5968 (6)0.2640 (3)0.2637 (4)0.0421 (13)
H710.5051430.2655410.2703540.051*
C7110.6437 (12)0.3244 (3)0.2413 (5)0.077 (3)
H71A0.6191460.3512740.2888440.116*
H71B0.6076240.3366750.1817690.116*
H71C0.7341570.3238950.2391250.116*
N310.6566 (5)0.2436 (2)0.3511 (3)0.0349 (9)
H31N0.690 (7)0.269 (4)0.371 (6)0.05 (2)*
C810.6312 (5)0.1899 (3)0.3814 (4)0.0342 (11)
O210.5713 (4)0.1548 (2)0.3324 (3)0.0404 (9)
C910.6750 (5)0.1737 (3)0.4800 (4)0.0331 (10)
C1010.6844 (4)0.1144 (3)0.5010 (4)0.0368 (11)
H1010.6680830.0866480.4545880.044*
C1110.7185 (5)0.0968 (3)0.5921 (4)0.0382 (11)
C1210.7434 (5)0.1384 (3)0.6610 (4)0.0374 (12)
H1210.7686700.1266050.7211080.045*
C1310.7311 (5)0.1973 (3)0.6411 (4)0.0350 (11)
C1410.6965 (4)0.2153 (3)0.5498 (4)0.0329 (10)
H1410.6879220.2549230.5360380.039*
C1510.7246 (6)0.0342 (3)0.6187 (5)0.0496 (15)
O310.7556 (6)0.0165 (3)0.6956 (4)0.0679 (15)
O410.6941 (5)0.0006 (2)0.5467 (4)0.0603 (13)
C1610.6901 (10)0.0630 (4)0.5648 (8)0.079 (3)
H16A0.7747900.0778240.5721750.118*
H16B0.6468670.0823540.5131910.118*
H16C0.6461650.0700160.6209290.118*
C1810.7532 (5)0.2412 (3)0.7173 (4)0.0415 (13)
O510.8087 (5)0.2285 (3)0.7925 (3)0.0582 (12)
O610.7078 (5)0.2932 (2)0.6982 (3)0.0482 (10)
C1910.7222 (10)0.3364 (5)0.7724 (6)0.072 (2)
H19A0.6860510.3216220.8279800.108*
H19B0.6796510.3718540.7533420.108*
H19C0.8103540.3443760.7847550.108*
N120.7595 (4)0.0383 (2)0.0230 (3)0.0318 (9)
C120.8619 (5)0.0300 (3)0.0278 (4)0.0412 (12)
H120.9243340.0586160.0260150.049*
C220.8788 (6)0.0188 (3)0.0826 (5)0.0489 (15)
H220.9505660.0227800.1172000.059*
C320.7860 (6)0.0622 (3)0.0849 (4)0.0451 (13)
H320.7940670.0952380.1220120.054*
C420.6825 (5)0.0552 (3)0.0314 (4)0.0390 (12)
H420.6205540.0840590.0304990.047*
C520.6712 (4)0.0043 (2)0.0218 (3)0.0307 (10)
N220.5612 (4)0.0013 (2)0.0718 (3)0.0310 (9)
H22N0.505 (6)0.033 (3)0.064 (5)0.034 (16)*
C620.5324 (4)0.0412 (2)0.1374 (3)0.0283 (9)
O120.6017 (3)0.08215 (17)0.1641 (3)0.0322 (7)
C720.4022 (4)0.0358 (2)0.1767 (3)0.0301 (10)
H720.3757770.0052430.1761860.036*
C7120.3100 (5)0.0720 (3)0.1148 (4)0.0433 (13)
H71D0.2260670.0677830.1367590.065*
H71E0.3117110.0583490.0514300.065*
H71F0.3342800.1124050.1174830.065*
N320.4087 (4)0.0577 (2)0.2721 (3)0.0292 (8)
H32N0.444 (5)0.091 (3)0.286 (4)0.018 (12)*
C820.3515 (5)0.0287 (2)0.3405 (3)0.0312 (10)
O220.2924 (4)0.01705 (19)0.3275 (3)0.0401 (9)
C920.3603 (4)0.0569 (2)0.4350 (3)0.0294 (10)
C1020.3602 (4)0.1171 (3)0.4463 (3)0.0298 (9)
H1020.3568980.1414460.3941900.036*
C1120.3649 (4)0.1413 (2)0.5365 (4)0.0309 (10)
C1220.3688 (4)0.1048 (2)0.6144 (3)0.0327 (11)
H1220.3707730.1207860.6741420.039*
C1320.3698 (5)0.0448 (3)0.6030 (4)0.0338 (11)
C1420.3645 (5)0.0206 (2)0.5137 (4)0.0317 (10)
H1420.3637710.0198390.5064190.038*
C1520.3689 (5)0.2051 (3)0.5527 (4)0.0351 (11)
O320.3798 (4)0.2276 (2)0.6295 (3)0.0470 (10)
O420.3619 (5)0.2356 (2)0.4727 (3)0.0507 (11)
C1620.3677 (9)0.2981 (3)0.4822 (5)0.0626 (19)
H16D0.2979450.3114040.5171430.094*
H16E0.3634270.3157880.4212550.094*
H16F0.4456720.3088890.5143930.094*
C1820.3763 (6)0.0041 (3)0.6846 (4)0.0408 (12)
O520.3863 (7)0.0474 (2)0.6800 (4)0.0712 (17)
O620.3680 (5)0.0329 (2)0.7653 (3)0.0508 (11)
C1920.3694 (9)0.0025 (4)0.8485 (4)0.066 (2)
H19D0.2992230.0291190.8449720.099*
H19E0.3628860.0222600.9022720.099*
H19F0.4469290.0242330.8537770.099*
N130.8839 (4)0.0971 (2)0.2055 (3)0.0301 (8)
C130.8494 (5)0.0566 (3)0.2679 (4)0.0370 (11)
H130.7713160.0384390.2582770.044*
C230.9235 (5)0.0408 (3)0.3452 (4)0.0388 (12)
H230.8965170.0125180.3864720.047*
C331.0400 (5)0.0683 (3)0.3600 (4)0.0382 (12)
H331.0926940.0583400.4111970.046*
C431.0759 (4)0.1103 (3)0.2977 (4)0.0342 (11)
H431.1531100.1293340.3066970.041*
C530.9956 (4)0.1241 (3)0.2210 (3)0.0287 (9)
N231.0358 (4)0.1675 (2)0.1599 (3)0.0309 (9)
H23N1.097 (6)0.183 (3)0.178 (4)0.022 (14)*
C630.9920 (4)0.1806 (2)0.0721 (3)0.0298 (10)
O130.8994 (3)0.15749 (19)0.0319 (2)0.0347 (8)
C731.0637 (5)0.2292 (3)0.0245 (4)0.0361 (11)
H731.1509520.2306600.0501050.043*
C7130.9981 (9)0.2870 (3)0.0429 (5)0.0606 (19)
H71G1.0428350.3182200.0140440.091*
H71H0.9970700.2936400.1090640.091*
H71I0.9128690.2855960.0170960.091*
N331.0632 (4)0.2175 (2)0.0763 (3)0.0367 (10)
H33N1.026 (13)0.245 (8)0.115 (10)0.13 (5)*
C831.1061 (5)0.1655 (3)0.1035 (4)0.0342 (10)
O231.1546 (4)0.1303 (2)0.0487 (3)0.0446 (10)
C931.0900 (5)0.1517 (3)0.2068 (4)0.0333 (11)
C1031.0804 (5)0.0930 (3)0.2299 (4)0.0368 (12)
H1031.0897370.0648110.1833240.044*
C1131.0567 (5)0.0760 (3)0.3226 (4)0.0365 (11)
C1231.0445 (4)0.1187 (3)0.3913 (3)0.0363 (10)
H1231.0274720.1077420.4531670.044*
C1331.0575 (5)0.1777 (3)0.3687 (4)0.0373 (12)
C1431.0797 (4)0.1942 (3)0.2758 (4)0.0349 (11)
H1431.0875590.2335980.2600870.042*
C1531.0421 (6)0.0138 (3)0.3487 (4)0.0438 (13)
O331.0154 (5)0.0034 (2)0.4271 (3)0.0555 (12)
O431.0640 (4)0.0221 (2)0.2746 (3)0.0471 (10)
C1631.0498 (9)0.0834 (4)0.2907 (6)0.0627 (19)
H16G0.9646310.0914570.3127440.094*
H16H1.0677520.1041960.2333900.094*
H16I1.1073440.0956980.3367900.094*
C1831.0489 (5)0.2246 (3)0.4408 (4)0.0406 (13)
O531.0657 (5)0.2753 (2)0.4255 (4)0.0586 (12)
O631.0209 (5)0.2026 (2)0.5265 (3)0.0512 (11)
C1931.0115 (9)0.2443 (4)0.6028 (5)0.064 (2)
H19G0.9721160.2794860.5819250.096*
H19H0.9615150.2278150.6538700.096*
H19I1.0945090.2531390.6231280.096*
N140.2542 (4)0.2835 (2)0.2067 (4)0.0388 (10)
O140.2557 (4)0.2296 (2)0.2216 (4)0.0505 (11)
O240.3283 (4)0.3041 (2)0.1483 (4)0.0532 (11)
O340.1833 (6)0.3166 (3)0.2466 (5)0.081 (2)
N150.3466 (5)0.1176 (3)0.0067 (4)0.0484 (13)
O150.3525 (5)0.0676 (2)0.0414 (4)0.0590 (13)
O250.4418 (7)0.1482 (3)0.0040 (5)0.0773 (17)
O350.2434 (7)0.1343 (4)0.0260 (6)0.100 (3)
N160.7679 (7)0.3456 (3)0.4726 (5)0.0627 (16)
C160.8357 (7)0.3690 (3)0.5245 (4)0.0462 (13)
C260.9231 (7)0.3995 (3)0.5882 (5)0.0497 (14)
H26A0.9883020.4174140.5535100.075*
H26B0.9603770.3722020.6323410.075*
H26C0.8785040.4291090.6210880.075*
N171.0742 (11)0.3678 (9)0.8306 (7)0.150 (7)
C171.0102 (9)0.4064 (7)0.8423 (6)0.089 (4)
C270.9280 (8)0.4552 (5)0.8581 (6)0.072 (2)
H27A0.8797730.4640690.8014880.108*
H27B0.9777980.4886890.8768100.108*
H27C0.8716870.4455640.9065400.108*
N180.3658 (9)0.4510 (4)0.6973 (8)0.091 (3)
C180.3738 (9)0.4055 (5)0.7285 (7)0.073 (2)
C280.3794 (12)0.3481 (5)0.7731 (9)0.095 (3)
H28A0.4202420.3514320.8340490.142*
H28B0.4264190.3216930.7356430.142*
H28C0.2952180.3333290.7787740.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0286 (3)0.0325 (3)0.0257 (3)0.0009 (2)0.0033 (2)0.0006 (3)
N110.0291 (18)0.037 (2)0.0246 (19)0.0003 (16)0.0007 (14)0.0006 (17)
C110.041 (3)0.052 (3)0.029 (2)0.001 (2)0.002 (2)0.005 (2)
C210.042 (3)0.069 (4)0.026 (2)0.000 (3)0.003 (2)0.007 (3)
C310.037 (2)0.061 (4)0.032 (3)0.001 (2)0.003 (2)0.005 (3)
C410.035 (2)0.043 (3)0.038 (3)0.002 (2)0.002 (2)0.001 (2)
C510.032 (2)0.032 (3)0.027 (2)0.0037 (18)0.0014 (17)0.001 (2)
N210.038 (2)0.035 (2)0.028 (2)0.0051 (18)0.0012 (16)0.0044 (18)
C610.038 (2)0.027 (2)0.028 (2)0.0037 (19)0.0003 (18)0.0028 (19)
O110.0356 (17)0.0320 (19)0.0267 (16)0.0004 (14)0.0020 (13)0.0012 (14)
C710.057 (3)0.036 (3)0.033 (3)0.007 (2)0.004 (2)0.004 (2)
C7110.160 (9)0.030 (4)0.040 (4)0.006 (4)0.019 (5)0.004 (3)
N310.047 (2)0.030 (2)0.028 (2)0.0037 (19)0.0021 (18)0.0048 (18)
C810.034 (2)0.037 (3)0.032 (2)0.005 (2)0.0017 (19)0.005 (2)
O210.0435 (19)0.044 (2)0.0339 (19)0.0117 (17)0.0041 (15)0.0057 (17)
C910.032 (2)0.038 (3)0.029 (2)0.0024 (19)0.0040 (18)0.001 (2)
C1010.031 (2)0.039 (3)0.041 (3)0.002 (2)0.0080 (18)0.002 (2)
C1110.032 (2)0.038 (3)0.045 (3)0.000 (2)0.006 (2)0.003 (2)
C1210.038 (2)0.044 (3)0.030 (2)0.002 (2)0.0062 (19)0.003 (2)
C1310.033 (2)0.042 (3)0.030 (2)0.000 (2)0.0083 (19)0.002 (2)
C1410.033 (2)0.036 (3)0.030 (2)0.0026 (19)0.0048 (18)0.001 (2)
C1510.048 (3)0.042 (4)0.059 (4)0.003 (3)0.004 (3)0.002 (3)
O310.101 (4)0.045 (3)0.058 (3)0.005 (3)0.000 (3)0.011 (2)
O410.081 (3)0.034 (3)0.065 (3)0.001 (2)0.007 (3)0.001 (2)
C1610.103 (7)0.035 (4)0.096 (7)0.002 (4)0.009 (5)0.002 (4)
C1810.044 (3)0.049 (4)0.031 (3)0.004 (2)0.010 (2)0.003 (2)
O510.082 (3)0.061 (3)0.030 (2)0.013 (3)0.006 (2)0.000 (2)
O610.069 (3)0.041 (2)0.034 (2)0.005 (2)0.0003 (18)0.0065 (18)
C1910.093 (6)0.071 (6)0.053 (4)0.001 (4)0.005 (4)0.017 (4)
N120.0337 (19)0.035 (2)0.027 (2)0.0002 (17)0.0084 (16)0.0053 (18)
C120.039 (3)0.043 (3)0.042 (3)0.001 (2)0.014 (2)0.005 (3)
C220.053 (3)0.046 (4)0.049 (3)0.001 (3)0.022 (3)0.012 (3)
C320.050 (3)0.045 (3)0.041 (3)0.006 (3)0.013 (2)0.009 (3)
C420.043 (3)0.034 (3)0.040 (3)0.001 (2)0.004 (2)0.007 (2)
C520.032 (2)0.032 (3)0.028 (2)0.0018 (18)0.0050 (18)0.001 (2)
N220.0329 (19)0.032 (2)0.029 (2)0.0014 (16)0.0049 (16)0.0059 (17)
C620.034 (2)0.029 (2)0.021 (2)0.0009 (18)0.0043 (17)0.0021 (19)
O120.0323 (16)0.0329 (19)0.0320 (18)0.0060 (14)0.0083 (13)0.0063 (15)
C720.032 (2)0.035 (3)0.024 (2)0.0002 (19)0.0022 (17)0.0039 (19)
C7120.035 (2)0.062 (4)0.033 (3)0.010 (2)0.001 (2)0.003 (3)
N320.0305 (18)0.031 (2)0.027 (2)0.0060 (16)0.0060 (15)0.0026 (17)
C820.036 (2)0.032 (3)0.026 (2)0.0016 (19)0.0057 (18)0.0006 (19)
O220.052 (2)0.036 (2)0.0322 (18)0.0133 (17)0.0072 (16)0.0032 (16)
C920.031 (2)0.035 (3)0.023 (2)0.0034 (18)0.0028 (17)0.0009 (19)
C1020.0282 (18)0.034 (3)0.027 (2)0.003 (2)0.0027 (15)0.002 (2)
C1120.029 (2)0.034 (3)0.029 (2)0.0001 (17)0.0033 (17)0.001 (2)
C1220.032 (2)0.043 (3)0.024 (2)0.0011 (18)0.0024 (17)0.0035 (19)
C1320.037 (2)0.039 (3)0.026 (2)0.003 (2)0.0032 (18)0.004 (2)
C1420.039 (2)0.030 (3)0.026 (2)0.0035 (19)0.0029 (18)0.003 (2)
C1520.040 (2)0.035 (3)0.030 (3)0.003 (2)0.0039 (19)0.002 (2)
O320.065 (2)0.038 (2)0.037 (2)0.0005 (19)0.0020 (18)0.0095 (19)
O420.083 (3)0.033 (2)0.036 (2)0.005 (2)0.003 (2)0.0005 (18)
C1620.106 (6)0.035 (4)0.048 (4)0.006 (4)0.009 (4)0.004 (3)
C1820.056 (3)0.042 (3)0.024 (2)0.005 (2)0.002 (2)0.003 (2)
O520.138 (5)0.037 (3)0.038 (2)0.002 (3)0.005 (3)0.011 (2)
O620.076 (3)0.053 (3)0.0235 (18)0.003 (2)0.0033 (18)0.0049 (18)
C1920.101 (6)0.073 (5)0.024 (3)0.001 (4)0.004 (3)0.012 (3)
N130.0325 (19)0.032 (2)0.0254 (19)0.0005 (16)0.0015 (15)0.0048 (16)
C130.034 (2)0.039 (3)0.039 (3)0.001 (2)0.004 (2)0.009 (2)
C230.042 (3)0.043 (3)0.033 (3)0.005 (2)0.009 (2)0.008 (2)
C330.038 (2)0.051 (4)0.026 (2)0.007 (2)0.0010 (19)0.002 (2)
C430.030 (2)0.043 (3)0.030 (2)0.0037 (19)0.0033 (17)0.001 (2)
C530.0294 (18)0.032 (2)0.0247 (19)0.002 (2)0.0056 (15)0.002 (2)
N230.033 (2)0.035 (2)0.0248 (19)0.0040 (18)0.0019 (16)0.0016 (17)
C630.029 (2)0.032 (3)0.029 (2)0.0010 (18)0.0063 (17)0.002 (2)
O130.0304 (16)0.048 (2)0.0253 (16)0.0024 (15)0.0016 (13)0.0040 (15)
C730.042 (3)0.037 (3)0.030 (3)0.003 (2)0.007 (2)0.003 (2)
C7130.100 (5)0.034 (3)0.050 (4)0.006 (3)0.026 (4)0.001 (3)
N330.043 (2)0.038 (3)0.029 (2)0.0035 (19)0.0065 (17)0.0037 (19)
C830.032 (2)0.037 (3)0.033 (2)0.001 (2)0.0023 (18)0.005 (2)
O230.054 (2)0.048 (3)0.0306 (18)0.0117 (19)0.0039 (15)0.0036 (18)
C930.029 (2)0.044 (3)0.027 (2)0.002 (2)0.0053 (17)0.002 (2)
C1030.035 (2)0.045 (3)0.031 (3)0.004 (2)0.0084 (19)0.005 (2)
C1130.035 (2)0.044 (3)0.031 (2)0.004 (2)0.0093 (19)0.002 (2)
C1230.037 (2)0.046 (3)0.026 (2)0.003 (2)0.0089 (17)0.003 (3)
C1330.032 (2)0.052 (3)0.029 (2)0.005 (2)0.0087 (19)0.010 (2)
C1430.029 (2)0.040 (3)0.036 (3)0.0008 (19)0.0079 (19)0.004 (2)
C1530.047 (3)0.051 (4)0.035 (3)0.004 (2)0.014 (2)0.008 (3)
O330.079 (3)0.056 (3)0.032 (2)0.004 (2)0.008 (2)0.007 (2)
O430.064 (3)0.043 (2)0.036 (2)0.0057 (19)0.0155 (18)0.0007 (18)
C1630.091 (5)0.045 (4)0.053 (4)0.005 (4)0.022 (4)0.000 (3)
C1830.044 (3)0.049 (4)0.030 (3)0.014 (2)0.012 (2)0.009 (2)
O530.087 (3)0.048 (3)0.042 (2)0.013 (2)0.005 (2)0.007 (2)
O630.076 (3)0.051 (3)0.0263 (19)0.012 (2)0.0092 (18)0.0044 (19)
C1930.105 (6)0.059 (5)0.030 (3)0.024 (4)0.015 (3)0.011 (3)
N140.035 (2)0.042 (3)0.039 (2)0.0004 (18)0.0032 (18)0.001 (2)
O140.043 (2)0.042 (3)0.065 (3)0.0072 (18)0.0091 (19)0.011 (2)
O240.054 (2)0.051 (3)0.057 (3)0.008 (2)0.023 (2)0.013 (2)
O340.094 (4)0.075 (4)0.076 (4)0.034 (3)0.050 (3)0.017 (3)
N150.065 (3)0.047 (3)0.035 (3)0.021 (3)0.011 (2)0.005 (2)
O150.059 (3)0.052 (3)0.067 (3)0.014 (2)0.011 (2)0.020 (3)
O250.095 (4)0.055 (4)0.084 (4)0.009 (3)0.024 (3)0.002 (3)
O350.080 (4)0.122 (7)0.098 (5)0.047 (4)0.013 (4)0.046 (5)
N160.092 (4)0.046 (3)0.049 (3)0.020 (3)0.003 (3)0.003 (3)
C160.067 (4)0.037 (3)0.035 (3)0.003 (3)0.008 (3)0.002 (2)
C260.065 (4)0.045 (4)0.039 (3)0.002 (3)0.001 (3)0.008 (3)
N170.109 (7)0.27 (2)0.068 (6)0.096 (11)0.011 (5)0.028 (9)
C170.064 (5)0.157 (12)0.046 (4)0.015 (6)0.001 (4)0.027 (6)
C270.064 (4)0.098 (7)0.054 (4)0.011 (4)0.004 (3)0.013 (5)
N180.093 (6)0.057 (5)0.123 (8)0.008 (4)0.013 (5)0.004 (5)
C180.077 (5)0.063 (6)0.077 (6)0.014 (4)0.005 (4)0.023 (5)
C280.101 (7)0.070 (7)0.113 (9)0.022 (6)0.005 (6)0.013 (6)
Geometric parameters (Å, º) top
Zn—O122.058 (3)C122—H1220.9300
Zn—O132.066 (4)C132—C1421.391 (8)
Zn—N132.128 (4)C132—C1821.494 (8)
Zn—O112.130 (4)C142—H1420.9300
Zn—N112.134 (4)C152—O321.215 (7)
Zn—N122.174 (5)C152—O421.339 (7)
N11—C111.342 (7)O42—C1621.436 (9)
N11—C511.343 (7)C162—H16D0.9600
C11—C211.373 (8)C162—H16E0.9600
C11—H110.9300C162—H16F0.9600
C21—C311.391 (10)C182—O521.183 (9)
C21—H210.9300C182—O621.335 (8)
C31—C411.377 (9)O62—C1921.440 (8)
C31—H310.9300C192—H19D0.9600
C41—C511.405 (7)C192—H19E0.9600
C41—H410.9300C192—H19F0.9600
C51—N211.391 (7)N13—C531.343 (6)
N21—C611.353 (7)N13—C131.348 (7)
N21—H21N0.90 (7)C13—C231.376 (8)
C61—O111.229 (7)C13—H130.9300
C61—C711.525 (8)C23—C331.391 (8)
C71—N311.454 (7)C23—H230.9300
C71—C7111.508 (11)C33—C431.375 (8)
C71—H710.9800C33—H330.9300
C711—H71A0.9600C43—C531.396 (7)
C711—H71B0.9600C43—H430.9300
C711—H71C0.9600C53—N231.401 (7)
N31—C811.333 (8)N23—C631.352 (6)
N31—H31N0.74 (9)N23—H23N0.77 (7)
C81—O211.224 (7)C63—O131.234 (6)
C81—C911.513 (7)C63—C731.524 (7)
C91—C1411.391 (8)C73—N331.466 (7)
C91—C1011.391 (9)C73—C7131.521 (9)
C101—C1111.397 (8)C73—H730.9800
C101—H1010.9300C713—H71G0.9600
C111—C1211.388 (9)C713—H71H0.9600
C111—C1511.481 (10)C713—H71I0.9600
C121—C1311.381 (9)N33—C831.337 (8)
C121—H1210.9300N33—H33N0.92 (16)
C131—C1411.403 (8)C83—O231.220 (7)
C131—C1811.492 (8)C83—C931.513 (7)
C141—H1410.9300C93—C1031.384 (8)
C151—O311.204 (9)C93—C1431.386 (8)
C151—O411.330 (9)C103—C1131.394 (8)
O41—C1611.451 (10)C103—H1030.9300
C161—H16A0.9600C113—C1231.388 (8)
C161—H16B0.9600C113—C1531.476 (10)
C161—H16C0.9600C123—C1331.393 (10)
C181—O511.237 (8)C123—H1230.9300
C181—O611.308 (9)C133—C1431.393 (8)
O61—C1911.453 (9)C133—C1831.490 (8)
C191—H19A0.9600C143—H1430.9300
C191—H19B0.9600C153—O331.211 (8)
C191—H19C0.9600C153—O431.353 (8)
N12—C121.346 (7)O43—C1631.426 (10)
N12—C521.349 (7)C163—H16G0.9600
C12—C221.380 (9)C163—H16H0.9600
C12—H120.9300C163—H16I0.9600
C22—C321.395 (10)C183—O531.189 (9)
C22—H220.9300C183—O631.346 (8)
C32—C421.374 (8)O63—C1931.449 (8)
C32—H320.9300C193—H19G0.9600
C42—C521.398 (8)C193—H19H0.9600
C42—H420.9300C193—H19I0.9600
C52—N221.400 (6)N14—O341.225 (8)
N22—C621.353 (7)N14—O141.252 (7)
N22—H22N0.98 (7)N14—O241.262 (7)
C62—O121.240 (6)N15—O251.228 (9)
C62—C721.516 (6)N15—O351.230 (8)
C72—N321.453 (6)N15—O151.248 (8)
C72—C7121.531 (7)N16—C161.141 (9)
C72—H720.9800C16—C261.450 (9)
C712—H71D0.9600C26—H26A0.9600
C712—H71E0.9600C26—H26B0.9600
C712—H71F0.9600C26—H26C0.9600
N32—C821.349 (7)N17—C171.130 (19)
N32—H32N0.87 (6)C17—C271.440 (17)
C82—O221.228 (7)C27—H27A0.9600
C82—C921.498 (7)C27—H27B0.9600
C92—C1021.385 (8)C27—H27C0.9600
C92—C1421.399 (7)N18—C181.133 (14)
C102—C1121.403 (7)C18—C281.459 (17)
C102—H1020.9300C28—H28A0.9600
C112—C1221.391 (7)C28—H28B0.9600
C112—C1521.477 (8)C28—H28C0.9600
C122—C1321.380 (8)
O12—Zn—O13178.36 (17)C92—C102—H102120.1
O12—Zn—N1393.15 (15)C112—C102—H102120.1
O13—Zn—N1385.72 (15)C122—C112—C102119.9 (5)
O12—Zn—O1190.60 (15)C122—C112—C152117.9 (5)
O13—Zn—O1190.47 (15)C102—C112—C152122.2 (5)
N13—Zn—O1184.80 (16)C132—C122—C112120.1 (5)
O12—Zn—N1190.11 (15)C132—C122—H122119.9
O13—Zn—N1191.23 (15)C112—C122—H122119.9
N13—Zn—N11168.71 (18)C122—C132—C142120.2 (5)
O11—Zn—N1184.36 (16)C122—C132—C182121.9 (5)
O12—Zn—N1284.93 (16)C142—C132—C182117.9 (5)
O13—Zn—N1293.99 (16)C132—C142—C92120.1 (5)
N13—Zn—N1295.02 (17)C132—C142—H142120.0
O11—Zn—N12175.52 (16)C92—C142—H142120.0
N11—Zn—N1296.03 (17)O32—C152—O42123.5 (6)
C11—N11—C51117.6 (4)O32—C152—C112124.1 (5)
C11—N11—Zn118.2 (4)O42—C152—C112112.4 (5)
C51—N11—Zn123.9 (3)C152—O42—C162115.9 (5)
N11—C11—C21123.6 (6)O42—C162—H16D109.5
N11—C11—H11118.2O42—C162—H16E109.5
C21—C11—H11118.2H16D—C162—H16E109.5
C11—C21—C31118.7 (5)O42—C162—H16F109.5
C11—C21—H21120.6H16D—C162—H16F109.5
C31—C21—H21120.6H16E—C162—H16F109.5
C41—C31—C21119.0 (5)O52—C182—O62123.3 (6)
C41—C31—H31120.5O52—C182—C132125.3 (6)
C21—C31—H31120.5O62—C182—C132111.4 (5)
C31—C41—C51118.7 (5)C182—O62—C192116.0 (6)
C31—C41—H41120.7O62—C192—H19D109.5
C51—C41—H41120.7O62—C192—H19E109.5
N11—C51—N21120.8 (4)H19D—C192—H19E109.5
N11—C51—C41122.4 (5)O62—C192—H19F109.5
N21—C51—C41116.8 (5)H19D—C192—H19F109.5
C61—N21—C51128.9 (5)H19E—C192—H19F109.5
C61—N21—H21N113 (4)C53—N13—C13118.0 (4)
C51—N21—H21N116 (4)C53—N13—Zn124.2 (3)
O11—C61—N21125.5 (5)C13—N13—Zn117.5 (3)
O11—C61—C71121.8 (5)N13—C13—C23123.4 (5)
N21—C61—C71112.5 (5)N13—C13—H13118.3
C61—O11—Zn122.3 (3)C23—C13—H13118.3
N31—C71—C711109.9 (5)C13—C23—C33118.3 (5)
N31—C71—C61111.7 (5)C13—C23—H23120.8
C711—C71—C61108.4 (6)C33—C23—H23120.8
N31—C71—H71108.9C43—C33—C23119.0 (5)
C711—C71—H71108.9C43—C33—H33120.5
C61—C71—H71108.9C23—C33—H33120.5
C71—C711—H71A109.5C33—C43—C53119.4 (5)
C71—C711—H71B109.5C33—C43—H43120.3
H71A—C711—H71B109.5C53—C43—H43120.3
C71—C711—H71C109.5N13—C53—C43121.8 (5)
H71A—C711—H71C109.5N13—C53—N23120.8 (4)
H71B—C711—H71C109.5C43—C53—N23117.4 (4)
C81—N31—C71119.2 (5)C63—N23—C53129.4 (4)
C81—N31—H31N135 (6)C63—N23—H23N117 (5)
C71—N31—H31N105 (6)C53—N23—H23N113 (5)
O21—C81—N31121.7 (5)O13—C63—N23124.9 (5)
O21—C81—C91120.2 (5)O13—C63—C73120.3 (4)
N31—C81—C91118.1 (5)N23—C63—C73114.8 (4)
C141—C91—C101120.2 (5)C63—O13—Zn125.1 (3)
C141—C91—C81122.4 (5)N33—C73—C713110.3 (5)
C101—C91—C81117.2 (5)N33—C73—C63109.1 (5)
C91—C101—C111119.8 (6)C713—C73—C63108.4 (5)
C91—C101—H101120.1N33—C73—H73109.7
C111—C101—H101120.1C713—C73—H73109.7
C121—C111—C101119.8 (6)C63—C73—H73109.7
C121—C111—C151118.4 (6)C73—C713—H71G109.5
C101—C111—C151121.7 (6)C73—C713—H71H109.5
C131—C121—C111120.6 (5)H71G—C713—H71H109.5
C131—C121—H121119.7C73—C713—H71I109.5
C111—C121—H121119.7H71G—C713—H71I109.5
C121—C131—C141119.8 (5)H71H—C713—H71I109.5
C121—C131—C181119.6 (5)C83—N33—C73117.6 (5)
C141—C131—C181120.6 (6)C83—N33—H33N126 (10)
C91—C141—C131119.7 (5)C73—N33—H33N117 (10)
C91—C141—H141120.1O23—C83—N33122.5 (5)
C131—C141—H141120.1O23—C83—C93121.1 (5)
O31—C151—O41123.6 (7)N33—C83—C93116.4 (5)
O31—C151—C111124.5 (7)C103—C93—C143120.4 (5)
O41—C151—C111111.8 (6)C103—C93—C83116.0 (5)
C151—O41—C161117.2 (7)C143—C93—C83123.5 (5)
O41—C161—H16A109.5C93—C103—C113120.5 (5)
O41—C161—H16B109.5C93—C103—H103119.8
H16A—C161—H16B109.5C113—C103—H103119.8
O41—C161—H16C109.5C123—C113—C103119.0 (6)
H16A—C161—H16C109.5C123—C113—C153119.5 (5)
H16B—C161—H16C109.5C103—C113—C153121.5 (5)
O51—C181—O61123.4 (6)C113—C123—C133120.8 (5)
O51—C181—C131122.1 (6)C113—C123—H123119.6
O61—C181—C131114.5 (5)C133—C123—H123119.6
C181—O61—C191116.1 (6)C143—C133—C123119.7 (5)
O61—C191—H19A109.5C143—C133—C183117.9 (6)
O61—C191—H19B109.5C123—C133—C183122.3 (5)
H19A—C191—H19B109.5C93—C143—C133119.6 (6)
O61—C191—H19C109.5C93—C143—H143120.2
H19A—C191—H19C109.5C133—C143—H143120.2
H19B—C191—H19C109.5O33—C153—O43123.6 (7)
C12—N12—C52117.7 (5)O33—C153—C113124.4 (6)
C12—N12—Zn116.7 (4)O43—C153—C113111.9 (5)
C52—N12—Zn125.6 (3)C153—O43—C163117.1 (6)
N12—C12—C22123.3 (6)O43—C163—H16G109.5
N12—C12—H12118.4O43—C163—H16H109.5
C22—C12—H12118.4H16G—C163—H16H109.5
C12—C22—C32118.6 (5)O43—C163—H16I109.5
C12—C22—H22120.7H16G—C163—H16I109.5
C32—C22—H22120.7H16H—C163—H16I109.5
C42—C32—C22118.9 (6)O53—C183—O63123.9 (6)
C42—C32—H32120.5O53—C183—C133124.7 (6)
C22—C32—H32120.5O63—C183—C133111.4 (6)
C32—C42—C52119.2 (5)C183—O63—C193116.4 (6)
C32—C42—H42120.4O63—C193—H19G109.5
C52—C42—H42120.4O63—C193—H19H109.5
N12—C52—C42122.2 (5)H19G—C193—H19H109.5
N12—C52—N22121.2 (5)O63—C193—H19I109.5
C42—C52—N22116.6 (5)H19G—C193—H19I109.5
C62—N22—C52129.5 (4)H19H—C193—H19I109.5
C62—N22—H22N118 (4)O34—N14—O14122.2 (6)
C52—N22—H22N112 (4)O34—N14—O24119.3 (6)
O12—C62—N22125.0 (4)O14—N14—O24118.5 (5)
O12—C62—C72118.8 (4)O25—N15—O35121.9 (7)
N22—C62—C72116.1 (4)O25—N15—O15120.5 (6)
C62—O12—Zn129.2 (3)O35—N15—O15117.6 (7)
N32—C72—C62108.3 (4)N16—C16—C26178.4 (8)
N32—C72—C712111.2 (4)C16—C26—H26A109.5
C62—C72—C712108.0 (4)C16—C26—H26B109.5
N32—C72—H72109.8H26A—C26—H26B109.5
C62—C72—H72109.8C16—C26—H26C109.5
C712—C72—H72109.8H26A—C26—H26C109.5
C72—C712—H71D109.5H26B—C26—H26C109.5
C72—C712—H71E109.5N17—C17—C27179.4 (13)
H71D—C712—H71E109.5C17—C27—H27A109.5
C72—C712—H71F109.5C17—C27—H27B109.5
H71D—C712—H71F109.5H27A—C27—H27B109.5
H71E—C712—H71F109.5C17—C27—H27C109.5
C82—N32—C72120.6 (4)H27A—C27—H27C109.5
C82—N32—H32N118 (4)H27B—C27—H27C109.5
C72—N32—H32N122 (4)N18—C18—C28176.6 (12)
O22—C82—N32123.4 (5)C18—C28—H28A109.5
O22—C82—C92121.0 (5)C18—C28—H28B109.5
N32—C82—C92115.5 (5)H28A—C28—H28B109.5
C102—C92—C142119.7 (5)C18—C28—H28C109.5
C102—C92—C82122.2 (5)H28A—C28—H28C109.5
C142—C92—C82118.0 (5)H28B—C28—H28C109.5
C92—C102—C112119.9 (5)
C51—N11—C11—C210.5 (9)O22—C82—C92—C14234.0 (7)
Zn—N11—C11—C21173.8 (5)N32—C82—C92—C142147.9 (5)
N11—C11—C21—C310.9 (10)C142—C92—C102—C1120.4 (7)
C11—C21—C31—C411.9 (10)C82—C92—C102—C112178.1 (4)
C21—C31—C41—C511.5 (9)C92—C102—C112—C1220.5 (7)
C11—N11—C51—N21179.6 (5)C92—C102—C112—C152178.1 (4)
Zn—N11—C51—N216.4 (7)C102—C112—C122—C1320.9 (7)
C11—N11—C51—C410.9 (8)C152—C112—C122—C132177.8 (5)
Zn—N11—C51—C41173.1 (4)C112—C122—C132—C1421.2 (7)
C31—C41—C51—N110.1 (9)C112—C122—C132—C182178.8 (5)
C31—C41—C51—N21179.4 (5)C122—C132—C142—C921.1 (7)
N11—C51—N21—C6121.5 (9)C182—C132—C142—C92179.0 (5)
C41—C51—N21—C61159.0 (6)C102—C92—C142—C1320.7 (7)
C51—N21—C61—O119.6 (10)C82—C92—C142—C132178.5 (4)
C51—N21—C61—C71165.7 (6)C122—C112—C152—O322.7 (8)
N21—C61—O11—Zn28.1 (7)C102—C112—C152—O32175.9 (5)
C71—C61—O11—Zn157.0 (4)C122—C112—C152—O42178.7 (5)
O11—C61—C71—N3135.0 (8)C102—C112—C152—O422.7 (7)
N21—C61—C71—N31149.5 (5)O32—C152—O42—C1620.2 (9)
O11—C61—C71—C71186.3 (8)C112—C152—O42—C162178.8 (6)
N21—C61—C71—C71189.2 (7)C122—C132—C182—O52174.4 (7)
C711—C71—N31—C81177.5 (7)C142—C132—C182—O525.6 (10)
C61—C71—N31—C8157.1 (7)C122—C132—C182—O626.3 (8)
C71—N31—C81—O219.1 (8)C142—C132—C182—O62173.7 (5)
C71—N31—C81—C91169.1 (5)O52—C182—O62—C1921.2 (10)
O21—C81—C91—C141153.8 (5)C132—C182—O62—C192178.1 (6)
N31—C81—C91—C14124.5 (7)C53—N13—C13—C231.4 (8)
O21—C81—C91—C10121.5 (7)Zn—N13—C13—C23174.6 (5)
N31—C81—C91—C101160.3 (5)N13—C13—C23—C330.4 (9)
C141—C91—C101—C1111.5 (7)C13—C23—C33—C430.6 (9)
C81—C91—C101—C111176.9 (4)C23—C33—C43—C530.5 (8)
C91—C101—C111—C1210.3 (7)C13—N13—C53—C431.4 (8)
C91—C101—C111—C151177.4 (5)Zn—N13—C53—C43174.1 (4)
C101—C111—C121—C1312.0 (8)C13—N13—C53—N23178.6 (5)
C151—C111—C121—C131175.8 (5)Zn—N13—C53—N235.9 (7)
C111—C121—C131—C1411.8 (8)C33—C43—C53—N130.5 (8)
C111—C121—C131—C181177.5 (5)C33—C43—C53—N23179.5 (5)
C101—C91—C141—C1311.8 (7)N13—C53—N23—C6315.6 (8)
C81—C91—C141—C131176.9 (5)C43—C53—N23—C63164.4 (5)
C121—C131—C141—C910.1 (7)C53—N23—C63—O135.1 (9)
C181—C131—C141—C91179.3 (5)C53—N23—C63—C73177.1 (5)
C121—C111—C151—O313.7 (10)N23—C63—O13—Zn26.4 (7)
C101—C111—C151—O31178.5 (7)C73—C63—O13—Zn151.3 (4)
C121—C111—C151—O41177.7 (5)O13—C63—C73—N3334.9 (7)
C101—C111—C151—O410.1 (8)N23—C63—C73—N33147.2 (5)
O31—C151—O41—C1614.4 (12)O13—C63—C73—C71385.3 (7)
C111—C151—O41—C161176.9 (7)N23—C63—C73—C71392.6 (6)
C121—C131—C181—O5116.3 (8)C713—C73—N33—C83173.4 (5)
C141—C131—C181—O51164.5 (6)C63—C73—N33—C8354.4 (6)
C121—C131—C181—O61162.8 (5)C73—N33—C83—O236.4 (8)
C141—C131—C181—O6116.4 (7)C73—N33—C83—C93172.9 (4)
O51—C181—O61—C1911.9 (9)O23—C83—C93—C10326.8 (7)
C131—C181—O61—C191177.2 (6)N33—C83—C93—C103152.5 (5)
C52—N12—C12—C221.8 (9)O23—C83—C93—C143155.9 (5)
Zn—N12—C12—C22176.7 (5)N33—C83—C93—C14324.7 (7)
N12—C12—C22—C320.6 (11)C143—C93—C103—C1131.7 (8)
C12—C22—C32—C421.2 (10)C83—C93—C103—C113175.6 (4)
C22—C32—C42—C521.8 (10)C93—C103—C113—C1230.7 (8)
C12—N12—C52—C421.2 (8)C93—C103—C113—C153178.1 (5)
Zn—N12—C52—C42177.2 (4)C103—C113—C123—C1331.0 (7)
C12—N12—C52—N22179.1 (5)C153—C113—C123—C133179.8 (5)
Zn—N12—C52—N220.7 (7)C113—C123—C133—C1431.7 (7)
C32—C42—C52—N120.6 (9)C113—C123—C133—C183178.1 (5)
C32—C42—C52—N22177.4 (5)C103—C93—C143—C1331.0 (7)
N12—C52—N22—C6211.6 (8)C83—C93—C143—C133176.1 (4)
C42—C52—N22—C62170.4 (5)C123—C133—C143—C930.7 (7)
C52—N22—C62—O121.6 (9)C183—C133—C143—C93179.1 (4)
C52—N22—C62—C72178.6 (5)C123—C113—C153—O332.7 (9)
N22—C62—O12—Zn21.1 (8)C103—C113—C153—O33176.2 (6)
C72—C62—O12—Zn155.8 (3)C123—C113—C153—O43176.5 (5)
O12—C62—C72—N3232.2 (7)C103—C113—C153—O434.7 (7)
N22—C62—C72—N32150.6 (5)O33—C153—O43—C1632.4 (9)
O12—C62—C72—C71288.3 (6)C113—C153—O43—C163178.5 (6)
N22—C62—C72—C71288.9 (6)C143—C133—C183—O533.9 (8)
C62—C72—N32—C82136.6 (5)C123—C133—C183—O53175.9 (6)
C712—C72—N32—C82104.8 (6)C143—C133—C183—O63176.9 (5)
C72—N32—C82—O220.5 (8)C123—C133—C183—O633.3 (7)
C72—N32—C82—C92177.5 (4)O53—C183—O63—C1930.1 (9)
O22—C82—C92—C102143.8 (5)C133—C183—O63—C193179.3 (5)
N32—C82—C92—C10234.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N32—H32N···O210.87 (6)2.07 (6)2.916 (6)163 (5)
N33—H33N···O51i0.92 (16)2.63 (13)3.227 (7)123 (12)
N21—H21N···O140.90 (7)2.68 (7)3.336 (7)131 (6)
N21—H21N···O240.90 (7)1.99 (7)2.888 (7)176 (7)
N23—H23N···O14ii0.77 (7)2.06 (7)2.835 (6)176 (6)
N22—H22N···O150.98 (7)1.82 (7)2.733 (6)154 (6)
N31—H31N···N160.74 (9)2.39 (9)3.110 (8)165 (8)
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z.
Coordination bonds and angles (Å, °) in (1) top
BondsAngles between atoms from ligands1 and 22 and 3
Zn—N112.134 (4)N11—Zn—O1184.36 (16)
Zn—O112.130 (4)N12—Zn—O1284.93 (16)
Zn—N122.174 (5)N11—Zn—N1296.03 (17)
Zn—O122.058 (3)N11—Zn—O1290.11 (15)
Zn—N132.128 (4)N12—Zn—O11175.52 (16)
Zn—O132.066 (4)O11—Zn—O1290.60 (15)
N13—Zn—O1385.72 (15)
N11—Zn—N13168.71 (18)
N11—Zn—O1391.23 (15)
N12—Zn—N1395.02 (17)
N12—Zn—O1393.99 (16)
N13—Zn—O1184.80 (16)
N13—Zn—O1293.15 (15)
O11—Zn—O1390.47 (15)
O12—Zn—O13178.36 (17)
Selected torsion angles (°) in title complex (1) and in two Herrick dimers in BADGAR (Kokan et al., 2017) top
Torsion angle(1)BADGAR
(Fig. 3b)Dimer 1 (Fig. 3a)Dimer 2a
N11—C51—N21—C6121.5 (9) (sp)161.3 (6) (ap)157.6 (6) (ap)
N12—C52—N22—C62-11.6 (8) (sp)177.2 (5) (ap)-176.9 (6) (ap)
N13—C53—N23—C63-15.6 (8) (sp)
N21—C61—C71—N31149.5 (5) (ac)-150.0 (5) (ac)-153.1 (5) (ap)
N22—C62—C72—N32150.6 (5) (ap)-138.9 (5) (ac)-138.2 (5) (ac)
N23—C63—C73—N33147.2 (5) (ac)
C61—C71—N31—C81-57.1 (7) (sc)76.8 (6) (sc)80.2 (6) (sc)
C62—C72—N32—C82-136.6 (5) (ac)71.5 (6) (sc)70.2 (6) (sc)
C63—C73—N33—C83-54.4 (6) (sc)
N31—C81—C91—C101-160.3 (5) (ap)174.5 (5) (ap)173.3 (5) (ap)
N32—C82—C92—C10234.3 (7) (sp)172.8 (5) (ap)172.6 (4) (ap)
N33—C83—C93—C103-152.5 (5) (ap)
C101—C111—C151—O41-0.1 (8) (sp)-12.5 (13) (sp)-15.1 (12) (sp)
C102—C112—C152—O422.7 (7) (sp)-6.0 (10) (sp)-8.1 (10) (sp)
C103—C113—C153—O43-4.7 (7) (sp)
C141—C131—C181—O6116.4 (7) (sp)2.2 (9) (sp)-5.0 (9) (sp)
C142—C132—C182—O62-173.7 (5) (ap)12.9 (8) (sp)13.2 (8) (sp)
C143—C133—C183—O63-176.9 (5) (ap)
Stereochemical assignments of torsion angles are given in parentheses (ap = antiperiplanar, sp = synperiplanar, ac = anticlinal and sc = synclinal)

Note: (a) torsion angles in dimer 2 that are analogous to those in dimer 1 are defined by the atoms with labels where the last digits '1' and '2' are replaced with digits '3' and '4', respectively [atom labels from BADGAR (Kokan et al., 2017)].
Aromatic interactions in the title complex (1) (intramolecular and intermolecular) and in Herrick dimers in BADGAR (Kokan et al., 2017) top
Stacking interactionParametera
Θ (°)d (Å)R (Å)l (Å)α (°)
1b
Intramolecular (Figs. 1 and 3b)
Ph1···Ph2122.54.048 (3)3.4134 (19)2.17713.2 (2)
Intermolecular (Fig. 4a)
Ph3···Ph1i123.74.195 (3)3.490 (2)2.3287.0 (2)
Ph3···Ph2ii123.24.295 (3)3.5941 (19)2.3518.0 (2)
BADGARc
Ph1···Ph2 (dimer 1, Fig. 3a)115.73.931 (4)3.542 (2)1.7054.1 (3)
Ph3···Ph4 (dimer 2)118.64.018 (3)3.527 (2)1.9262.9 (3)
Notes: (a) parameters of stacking interactions are defined in Fig. 2 of Snyder et al. (2012b): Θ = displacement angle as the smaller of two angles defined by the ring-to-ring centroids with planes of the benzoyl rings; d = ring-centroid-to-ring-centroid distance; R = distance of ring centroid and plane defined by the opposite ring; l = horizontal displacement of two ring centroids; α = angle between planes of two benzoyl rings. (b) Ph1 = C91–C141, Ph2 = C92–C142 and Ph3 = C93–C143. (b) Ph1 = C91–C141 and Ph2 = C92–C142 for dimer 1, and Ph3 = C93–C143 and Ph4 = C94–C144 for dimer 2. Symmetry codes: (i) x, y, z-1; (ii) x+1, y, z-1.
Geometry parameters (Å, °) for hydrogen bonds in the title complex (1) (intramolecular and intermolecular) and in Herrick dimers in BADGAR (Kokan et al., 2017). top
D—H···AD—HH···AD···AD—H···A
1
Intramolecular (Figs. 1 and 2b)
N32—H32N···O210.87 (6)2.07 (6)2.916 (6)163 (5)
Intermolecular
Ligand–ligand (Fig. 3a)
N33—H33N···O51i0.92 (16)2.63 (13)3.227 (7)123 (12)
Ligand–anion (Fig. 3b)
N21—H21N···O140.90 (7)2.68 (7)3.336 (7)131 (6)
N21—H21N···O240.90 (7)1.99 (7)2.888 (7)176 (6)
N23—H23N···O14iii0.77 (7)2.06 (7)2.835 (6)176 (6)
N22—H22N···O150.98 (7)1.82 (7)2.733 (6)154 (6)
Ligand–solvent (Fig. 3b)
N31—H31N···N160.74 (9)2.39 (9)3.110 (8)165 (8)
BADGAR intradimer (Fig. 2a)
Dimer 1
N31—H31N···O120.862.032.845 (6)158
N32—H32N···O110.862.162.964 (6)156
Dimer 2
N33—H33N···O140.862.012.842 (6)163
N34—H34N···O130.862.162.971 (6)157
Symmetry codes: (i) x, y, z-1; (iii) x+1, y, z
 

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