Induction of Λ-helicity in a zinc com­plex with an alanine-appended amino­pyridine ligand

Perić, B.; Kokan, Z.; Kirin, S.I.

doi:10.1107/S2053229621006471

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Induction of Λ-helicity in a zinc complex with an alanine-appended aminopyridine ligand

B. Perić, Z. Kokan and S. I. Kirin

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.

Keywords: alanine; aminopyridine; supramolecular chirality; zinc complex; crystal structure; amino acid.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621006471/ef3020sup1.cif Contains datablocks I, global
	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)₂·3C₂H₃N	F(000) = 1528
M_r = 1468.66	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 10.5897 (2) Å	Cell parameters from 8319 reflections
b = 22.8595 (5) Å	θ = 3.6–74.5°
c = 14.3102 (3) Å	µ = 1.25 mm⁻¹
β = 92.524 (2)°	T = 136 K
V = 3460.78 (12) Å³	Prism, colourless
Z = 2	0.2 × 0.15 × 0.1 mm

Data collection top

Agilent Xcalibur Nova diffractometer with a Ruby detector	10880 independent reflections
Radiation source: sealed X-ray tube	10178 reflections with I > 2σ(I)
Detector resolution: 10.4323 pixels mm^-1	R_int = 0.038
ω scans	θ_max = 76.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −13→8
T_min = 0.658, T_max = 1.000	k = −25→28
19332 measured reflections	l = −16→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.077P)² + 1.8689P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
10880 reflections	Δρ_max = 0.86 e Å⁻³
955 parameters	Δρ_min = −0.66 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 3017 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute 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

	x	y	z	U_iso*/U_eq
Zn	0.74871 (5)	0.12080 (3)	0.09775 (4)	0.02888 (16)
N11	0.6173 (4)	0.1615 (2)	0.0009 (3)	0.0303 (8)
C11	0.6131 (5)	0.1429 (3)	−0.0882 (4)	0.0409 (12)
H11	0.673085	0.115735	−0.105695	0.049*
C21	0.5252 (5)	0.1617 (3)	−0.1548 (4)	0.0458 (14)
H21	0.526615	0.148033	−0.215989	0.055*
C31	0.4339 (5)	0.2017 (3)	−0.1292 (4)	0.0433 (13)
H31	0.371745	0.214330	−0.172481	0.052*
C41	0.4371 (5)	0.2223 (3)	−0.0387 (4)	0.0388 (12)
H41	0.378411	0.249726	−0.020141	0.047*
C51	0.5308 (4)	0.2010 (2)	0.0250 (3)	0.0303 (10)
N21	0.5299 (4)	0.2225 (2)	0.1159 (3)	0.0337 (9)
H21N	0.466 (6)	0.247 (3)	0.128 (5)	0.034 (16)*
C61	0.6249 (5)	0.2236 (2)	0.1824 (4)	0.0311 (10)
O11	0.7272 (3)	0.19862 (17)	0.1774 (2)	0.0314 (7)
C71	0.5968 (6)	0.2640 (3)	0.2637 (4)	0.0421 (13)
H71	0.505143	0.265541	0.270354	0.051*
C711	0.6437 (12)	0.3244 (3)	0.2413 (5)	0.077 (3)
H71A	0.619146	0.351274	0.288844	0.116*
H71B	0.607624	0.336675	0.181769	0.116*
H71C	0.734157	0.323895	0.239125	0.116*
N31	0.6566 (5)	0.2436 (2)	0.3511 (3)	0.0349 (9)
H31N	0.690 (7)	0.269 (4)	0.371 (6)	0.05 (2)*
C81	0.6312 (5)	0.1899 (3)	0.3814 (4)	0.0342 (11)
O21	0.5713 (4)	0.1548 (2)	0.3324 (3)	0.0404 (9)
C91	0.6750 (5)	0.1737 (3)	0.4800 (4)	0.0331 (10)
C101	0.6844 (4)	0.1144 (3)	0.5010 (4)	0.0368 (11)
H101	0.668083	0.086648	0.454588	0.044*
C111	0.7185 (5)	0.0968 (3)	0.5921 (4)	0.0382 (11)
C121	0.7434 (5)	0.1384 (3)	0.6610 (4)	0.0374 (12)
H121	0.768670	0.126605	0.721108	0.045*
C131	0.7311 (5)	0.1973 (3)	0.6411 (4)	0.0350 (11)
C141	0.6965 (4)	0.2153 (3)	0.5498 (4)	0.0329 (10)
H141	0.687922	0.254923	0.536038	0.039*
C151	0.7246 (6)	0.0342 (3)	0.6187 (5)	0.0496 (15)
O31	0.7556 (6)	0.0165 (3)	0.6956 (4)	0.0679 (15)
O41	0.6941 (5)	−0.0006 (2)	0.5467 (4)	0.0603 (13)
C161	0.6901 (10)	−0.0630 (4)	0.5648 (8)	0.079 (3)
H16A	0.774790	−0.077824	0.572175	0.118*
H16B	0.646867	−0.082354	0.513191	0.118*
H16C	0.646165	−0.070016	0.620929	0.118*
C181	0.7532 (5)	0.2412 (3)	0.7173 (4)	0.0415 (13)
O51	0.8087 (5)	0.2285 (3)	0.7925 (3)	0.0582 (12)
O61	0.7078 (5)	0.2932 (2)	0.6982 (3)	0.0482 (10)
C191	0.7222 (10)	0.3364 (5)	0.7724 (6)	0.072 (2)
H19A	0.686051	0.321622	0.827980	0.108*
H19B	0.679651	0.371854	0.753342	0.108*
H19C	0.810354	0.344376	0.784755	0.108*
N12	0.7595 (4)	0.0383 (2)	0.0230 (3)	0.0318 (9)
C12	0.8619 (5)	0.0300 (3)	−0.0278 (4)	0.0412 (12)
H12	0.924334	0.058616	−0.026015	0.049*
C22	0.8788 (6)	−0.0188 (3)	−0.0826 (5)	0.0489 (15)
H22	0.950566	−0.022780	−0.117200	0.059*
C32	0.7860 (6)	−0.0622 (3)	−0.0849 (4)	0.0451 (13)
H32	0.794067	−0.095238	−0.122012	0.054*
C42	0.6825 (5)	−0.0552 (3)	−0.0314 (4)	0.0390 (12)
H42	0.620554	−0.084059	−0.030499	0.047*
C52	0.6712 (4)	−0.0043 (2)	0.0218 (3)	0.0307 (10)
N22	0.5612 (4)	0.0013 (2)	0.0718 (3)	0.0310 (9)
H22N	0.505 (6)	−0.033 (3)	0.064 (5)	0.034 (16)*
C62	0.5324 (4)	0.0412 (2)	0.1374 (3)	0.0283 (9)
O12	0.6017 (3)	0.08215 (17)	0.1641 (3)	0.0322 (7)
C72	0.4022 (4)	0.0358 (2)	0.1767 (3)	0.0301 (10)
H72	0.375777	−0.005243	0.176186	0.036*
C712	0.3100 (5)	0.0720 (3)	0.1148 (4)	0.0433 (13)
H71D	0.226067	0.067783	0.136759	0.065*
H71E	0.311711	0.058349	0.051430	0.065*
H71F	0.334280	0.112405	0.117483	0.065*
N32	0.4087 (4)	0.0577 (2)	0.2721 (3)	0.0292 (8)
H32N	0.444 (5)	0.091 (3)	0.286 (4)	0.018 (12)*
C82	0.3515 (5)	0.0287 (2)	0.3405 (3)	0.0312 (10)
O22	0.2924 (4)	−0.01705 (19)	0.3275 (3)	0.0401 (9)
C92	0.3603 (4)	0.0569 (2)	0.4350 (3)	0.0294 (10)
C102	0.3602 (4)	0.1171 (3)	0.4463 (3)	0.0298 (9)
H102	0.356898	0.141446	0.394190	0.036*
C112	0.3649 (4)	0.1413 (2)	0.5365 (4)	0.0309 (10)
C122	0.3688 (4)	0.1048 (2)	0.6144 (3)	0.0327 (11)
H122	0.370773	0.120786	0.674142	0.039*
C132	0.3698 (5)	0.0448 (3)	0.6030 (4)	0.0338 (11)
C142	0.3645 (5)	0.0206 (2)	0.5137 (4)	0.0317 (10)
H142	0.363771	−0.019839	0.506419	0.038*
C152	0.3689 (5)	0.2051 (3)	0.5527 (4)	0.0351 (11)
O32	0.3798 (4)	0.2276 (2)	0.6295 (3)	0.0470 (10)
O42	0.3619 (5)	0.2356 (2)	0.4727 (3)	0.0507 (11)
C162	0.3677 (9)	0.2981 (3)	0.4822 (5)	0.0626 (19)
H16D	0.297945	0.311404	0.517143	0.094*
H16E	0.363427	0.315788	0.421255	0.094*
H16F	0.445672	0.308889	0.514393	0.094*
C182	0.3763 (6)	0.0041 (3)	0.6846 (4)	0.0408 (12)
O52	0.3863 (7)	−0.0474 (2)	0.6800 (4)	0.0712 (17)
O62	0.3680 (5)	0.0329 (2)	0.7653 (3)	0.0508 (11)
C192	0.3694 (9)	−0.0025 (4)	0.8485 (4)	0.066 (2)
H19D	0.299223	−0.029119	0.844972	0.099*
H19E	0.362886	0.022260	0.902272	0.099*
H19F	0.446929	−0.024233	0.853777	0.099*
N13	0.8839 (4)	0.0971 (2)	0.2055 (3)	0.0301 (8)
C13	0.8494 (5)	0.0566 (3)	0.2679 (4)	0.0370 (11)
H13	0.771316	0.038439	0.258277	0.044*
C23	0.9235 (5)	0.0408 (3)	0.3452 (4)	0.0388 (12)
H23	0.896517	0.012518	0.386472	0.047*
C33	1.0400 (5)	0.0683 (3)	0.3600 (4)	0.0382 (12)
H33	1.092694	0.058340	0.411197	0.046*
C43	1.0759 (4)	0.1103 (3)	0.2977 (4)	0.0342 (11)
H43	1.153110	0.129334	0.306697	0.041*
C53	0.9956 (4)	0.1241 (3)	0.2210 (3)	0.0287 (9)
N23	1.0358 (4)	0.1675 (2)	0.1599 (3)	0.0309 (9)
H23N	1.097 (6)	0.183 (3)	0.178 (4)	0.022 (14)*
C63	0.9920 (4)	0.1806 (2)	0.0721 (3)	0.0298 (10)
O13	0.8994 (3)	0.15749 (19)	0.0319 (2)	0.0347 (8)
C73	1.0637 (5)	0.2292 (3)	0.0245 (4)	0.0361 (11)
H73	1.150952	0.230660	0.050105	0.043*
C713	0.9981 (9)	0.2870 (3)	0.0429 (5)	0.0606 (19)
H71G	1.042835	0.318220	0.014044	0.091*
H71H	0.997070	0.293640	0.109064	0.091*
H71I	0.912869	0.285596	0.017096	0.091*
N33	1.0632 (4)	0.2175 (2)	−0.0763 (3)	0.0367 (10)
H33N	1.026 (13)	0.245 (8)	−0.115 (10)	0.13 (5)*
C83	1.1061 (5)	0.1655 (3)	−0.1035 (4)	0.0342 (10)
O23	1.1546 (4)	0.1303 (2)	−0.0487 (3)	0.0446 (10)
C93	1.0900 (5)	0.1517 (3)	−0.2068 (4)	0.0333 (11)
C103	1.0804 (5)	0.0930 (3)	−0.2299 (4)	0.0368 (12)
H103	1.089737	0.064811	−0.183324	0.044*
C113	1.0567 (5)	0.0760 (3)	−0.3226 (4)	0.0365 (11)
C123	1.0445 (4)	0.1187 (3)	−0.3913 (3)	0.0363 (10)
H123	1.027472	0.107742	−0.453167	0.044*
C133	1.0575 (5)	0.1777 (3)	−0.3687 (4)	0.0373 (12)
C143	1.0797 (4)	0.1942 (3)	−0.2758 (4)	0.0349 (11)
H143	1.087559	0.233598	−0.260087	0.042*
C153	1.0421 (6)	0.0138 (3)	−0.3487 (4)	0.0438 (13)
O33	1.0154 (5)	−0.0034 (2)	−0.4271 (3)	0.0555 (12)
O43	1.0640 (4)	−0.0221 (2)	−0.2746 (3)	0.0471 (10)
C163	1.0498 (9)	−0.0834 (4)	−0.2907 (6)	0.0627 (19)
H16G	0.964631	−0.091457	−0.312744	0.094*
H16H	1.067752	−0.104196	−0.233390	0.094*
H16I	1.107344	−0.095698	−0.336790	0.094*
C183	1.0489 (5)	0.2246 (3)	−0.4408 (4)	0.0406 (13)
O53	1.0657 (5)	0.2753 (2)	−0.4255 (4)	0.0586 (12)
O63	1.0209 (5)	0.2026 (2)	−0.5265 (3)	0.0512 (11)
C193	1.0115 (9)	0.2443 (4)	−0.6028 (5)	0.064 (2)
H19G	0.972116	0.279486	−0.581925	0.096*
H19H	0.961515	0.227815	−0.653870	0.096*
H19I	1.094509	0.253139	−0.623128	0.096*
N14	0.2542 (4)	0.2835 (2)	0.2067 (4)	0.0388 (10)
O14	0.2557 (4)	0.2296 (2)	0.2216 (4)	0.0505 (11)
O24	0.3283 (4)	0.3041 (2)	0.1483 (4)	0.0532 (11)
O34	0.1833 (6)	0.3166 (3)	0.2466 (5)	0.081 (2)
N15	0.3466 (5)	−0.1176 (3)	0.0067 (4)	0.0484 (13)
O15	0.3525 (5)	−0.0676 (2)	0.0414 (4)	0.0590 (13)
O25	0.4418 (7)	−0.1482 (3)	0.0040 (5)	0.0773 (17)
O35	0.2434 (7)	−0.1343 (4)	−0.0260 (6)	0.100 (3)
N16	0.7679 (7)	0.3456 (3)	0.4726 (5)	0.0627 (16)
C16	0.8357 (7)	0.3690 (3)	0.5245 (4)	0.0462 (13)
C26	0.9231 (7)	0.3995 (3)	0.5882 (5)	0.0497 (14)
H26A	0.988302	0.417414	0.553510	0.075*
H26B	0.960377	0.372202	0.632341	0.075*
H26C	0.878504	0.429109	0.621088	0.075*
N17	1.0742 (11)	0.3678 (9)	0.8306 (7)	0.150 (7)
C17	1.0102 (9)	0.4064 (7)	0.8423 (6)	0.089 (4)
C27	0.9280 (8)	0.4552 (5)	0.8581 (6)	0.072 (2)
H27A	0.879773	0.464069	0.801488	0.108*
H27B	0.977798	0.488689	0.876810	0.108*
H27C	0.871687	0.445564	0.906540	0.108*
N18	0.3658 (9)	0.4510 (4)	0.6973 (8)	0.091 (3)
C18	0.3738 (9)	0.4055 (5)	0.7285 (7)	0.073 (2)
C28	0.3794 (12)	0.3481 (5)	0.7731 (9)	0.095 (3)
H28A	0.420242	0.351432	0.834049	0.142*
H28B	0.426419	0.321693	0.735643	0.142*
H28C	0.295218	0.333329	0.778774	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0286 (3)	0.0325 (3)	0.0257 (3)	−0.0009 (2)	0.0033 (2)	−0.0006 (3)
N11	0.0291 (18)	0.037 (2)	0.0246 (19)	−0.0003 (16)	0.0007 (14)	0.0006 (17)
C11	0.041 (3)	0.052 (3)	0.029 (2)	0.001 (2)	−0.002 (2)	−0.005 (2)
C21	0.042 (3)	0.069 (4)	0.026 (2)	0.000 (3)	−0.003 (2)	−0.007 (3)
C31	0.037 (2)	0.061 (4)	0.032 (3)	−0.001 (2)	−0.003 (2)	0.005 (3)
C41	0.035 (2)	0.043 (3)	0.038 (3)	0.002 (2)	−0.002 (2)	0.001 (2)
C51	0.032 (2)	0.032 (3)	0.027 (2)	−0.0037 (18)	0.0014 (17)	−0.001 (2)
N21	0.038 (2)	0.035 (2)	0.028 (2)	0.0051 (18)	0.0012 (16)	−0.0044 (18)
C61	0.038 (2)	0.027 (2)	0.028 (2)	−0.0037 (19)	0.0003 (18)	−0.0028 (19)
O11	0.0356 (17)	0.0320 (19)	0.0267 (16)	−0.0004 (14)	0.0020 (13)	−0.0012 (14)
C71	0.057 (3)	0.036 (3)	0.033 (3)	0.007 (2)	−0.004 (2)	−0.004 (2)
C711	0.160 (9)	0.030 (4)	0.040 (4)	−0.006 (4)	−0.019 (5)	−0.004 (3)
N31	0.047 (2)	0.030 (2)	0.028 (2)	−0.0037 (19)	−0.0021 (18)	−0.0048 (18)
C81	0.034 (2)	0.037 (3)	0.032 (2)	−0.005 (2)	0.0017 (19)	−0.005 (2)
O21	0.0435 (19)	0.044 (2)	0.0339 (19)	−0.0117 (17)	0.0041 (15)	−0.0057 (17)
C91	0.032 (2)	0.038 (3)	0.029 (2)	−0.0024 (19)	0.0040 (18)	−0.001 (2)
C101	0.031 (2)	0.039 (3)	0.041 (3)	−0.002 (2)	0.0080 (18)	−0.002 (2)
C111	0.032 (2)	0.038 (3)	0.045 (3)	0.000 (2)	0.006 (2)	0.003 (2)
C121	0.038 (2)	0.044 (3)	0.030 (2)	0.002 (2)	0.0062 (19)	0.003 (2)
C131	0.033 (2)	0.042 (3)	0.030 (2)	0.000 (2)	0.0083 (19)	−0.002 (2)
C141	0.033 (2)	0.036 (3)	0.030 (2)	−0.0026 (19)	0.0048 (18)	0.001 (2)
C151	0.048 (3)	0.042 (4)	0.059 (4)	0.003 (3)	0.004 (3)	0.002 (3)
O31	0.101 (4)	0.045 (3)	0.058 (3)	0.005 (3)	0.000 (3)	0.011 (2)
O41	0.081 (3)	0.034 (3)	0.065 (3)	−0.001 (2)	−0.007 (3)	−0.001 (2)
C161	0.103 (7)	0.035 (4)	0.096 (7)	0.002 (4)	−0.009 (5)	0.002 (4)
C181	0.044 (3)	0.049 (4)	0.031 (3)	−0.004 (2)	0.010 (2)	−0.003 (2)
O51	0.082 (3)	0.061 (3)	0.030 (2)	0.013 (3)	−0.006 (2)	0.000 (2)
O61	0.069 (3)	0.041 (2)	0.034 (2)	0.005 (2)	−0.0003 (18)	−0.0065 (18)
C191	0.093 (6)	0.071 (6)	0.053 (4)	−0.001 (4)	0.005 (4)	−0.017 (4)
N12	0.0337 (19)	0.035 (2)	0.027 (2)	−0.0002 (17)	0.0084 (16)	−0.0053 (18)
C12	0.039 (3)	0.043 (3)	0.042 (3)	−0.001 (2)	0.014 (2)	−0.005 (3)
C22	0.053 (3)	0.046 (4)	0.049 (3)	0.001 (3)	0.022 (3)	−0.012 (3)
C32	0.050 (3)	0.045 (3)	0.041 (3)	0.006 (3)	0.013 (2)	−0.009 (3)
C42	0.043 (3)	0.034 (3)	0.040 (3)	−0.001 (2)	0.004 (2)	−0.007 (2)
C52	0.032 (2)	0.032 (3)	0.028 (2)	0.0018 (18)	0.0050 (18)	−0.001 (2)
N22	0.0329 (19)	0.032 (2)	0.029 (2)	−0.0014 (16)	0.0049 (16)	−0.0059 (17)
C62	0.034 (2)	0.029 (2)	0.021 (2)	−0.0009 (18)	0.0043 (17)	−0.0021 (19)
O12	0.0323 (16)	0.0329 (19)	0.0320 (18)	−0.0060 (14)	0.0083 (13)	−0.0063 (15)
C72	0.032 (2)	0.035 (3)	0.024 (2)	0.0002 (19)	0.0022 (17)	−0.0039 (19)
C712	0.035 (2)	0.062 (4)	0.033 (3)	0.010 (2)	0.001 (2)	−0.003 (3)
N32	0.0305 (18)	0.031 (2)	0.027 (2)	−0.0060 (16)	0.0060 (15)	−0.0026 (17)
C82	0.036 (2)	0.032 (3)	0.026 (2)	−0.0016 (19)	0.0057 (18)	−0.0006 (19)
O22	0.052 (2)	0.036 (2)	0.0322 (18)	−0.0133 (17)	0.0072 (16)	−0.0032 (16)
C92	0.031 (2)	0.035 (3)	0.023 (2)	−0.0034 (18)	0.0028 (17)	0.0009 (19)
C102	0.0282 (18)	0.034 (3)	0.027 (2)	−0.003 (2)	0.0027 (15)	0.002 (2)
C112	0.029 (2)	0.034 (3)	0.029 (2)	0.0001 (17)	0.0033 (17)	−0.001 (2)
C122	0.032 (2)	0.043 (3)	0.024 (2)	−0.0011 (18)	0.0024 (17)	−0.0035 (19)
C132	0.037 (2)	0.039 (3)	0.026 (2)	−0.003 (2)	0.0032 (18)	0.004 (2)
C142	0.039 (2)	0.030 (3)	0.026 (2)	−0.0035 (19)	0.0029 (18)	0.003 (2)
C152	0.040 (2)	0.035 (3)	0.030 (3)	0.003 (2)	0.0039 (19)	0.002 (2)
O32	0.065 (2)	0.038 (2)	0.037 (2)	0.0005 (19)	0.0020 (18)	−0.0095 (19)
O42	0.083 (3)	0.033 (2)	0.036 (2)	0.005 (2)	0.003 (2)	0.0005 (18)
C162	0.106 (6)	0.035 (4)	0.048 (4)	0.006 (4)	0.009 (4)	0.004 (3)
C182	0.056 (3)	0.042 (3)	0.024 (2)	−0.005 (2)	0.002 (2)	0.003 (2)
O52	0.138 (5)	0.037 (3)	0.038 (2)	−0.002 (3)	0.005 (3)	0.011 (2)
O62	0.076 (3)	0.053 (3)	0.0235 (18)	0.003 (2)	0.0033 (18)	0.0049 (18)
C192	0.101 (6)	0.073 (5)	0.024 (3)	0.001 (4)	0.004 (3)	0.012 (3)
N13	0.0325 (19)	0.032 (2)	0.0254 (19)	0.0005 (16)	0.0015 (15)	0.0048 (16)
C13	0.034 (2)	0.039 (3)	0.039 (3)	0.001 (2)	0.004 (2)	0.009 (2)
C23	0.042 (3)	0.043 (3)	0.033 (3)	0.005 (2)	0.009 (2)	0.008 (2)
C33	0.038 (2)	0.051 (4)	0.026 (2)	0.007 (2)	0.0010 (19)	0.002 (2)
C43	0.030 (2)	0.043 (3)	0.030 (2)	0.0037 (19)	0.0033 (17)	0.001 (2)
C53	0.0294 (18)	0.032 (2)	0.0247 (19)	0.002 (2)	0.0056 (15)	−0.002 (2)
N23	0.033 (2)	0.035 (2)	0.0248 (19)	−0.0040 (18)	0.0019 (16)	0.0016 (17)
C63	0.029 (2)	0.032 (3)	0.029 (2)	0.0010 (18)	0.0063 (17)	0.002 (2)
O13	0.0304 (16)	0.048 (2)	0.0253 (16)	−0.0024 (15)	0.0016 (13)	0.0040 (15)
C73	0.042 (3)	0.037 (3)	0.030 (3)	−0.003 (2)	0.007 (2)	0.003 (2)
C713	0.100 (5)	0.034 (3)	0.050 (4)	0.006 (3)	0.026 (4)	0.001 (3)
N33	0.043 (2)	0.038 (3)	0.029 (2)	0.0035 (19)	0.0065 (17)	0.0037 (19)
C83	0.032 (2)	0.037 (3)	0.033 (2)	−0.001 (2)	0.0023 (18)	0.005 (2)
O23	0.054 (2)	0.048 (3)	0.0306 (18)	0.0117 (19)	−0.0039 (15)	0.0036 (18)
C93	0.029 (2)	0.044 (3)	0.027 (2)	0.002 (2)	0.0053 (17)	0.002 (2)
C103	0.035 (2)	0.045 (3)	0.031 (3)	0.004 (2)	0.0084 (19)	0.005 (2)
C113	0.035 (2)	0.044 (3)	0.031 (2)	0.004 (2)	0.0093 (19)	0.002 (2)
C123	0.037 (2)	0.046 (3)	0.026 (2)	0.003 (2)	0.0089 (17)	0.003 (3)
C133	0.032 (2)	0.052 (3)	0.029 (2)	0.005 (2)	0.0087 (19)	0.010 (2)
C143	0.029 (2)	0.040 (3)	0.036 (3)	0.0008 (19)	0.0079 (19)	0.004 (2)
C153	0.047 (3)	0.051 (4)	0.035 (3)	0.004 (2)	0.014 (2)	0.008 (3)
O33	0.079 (3)	0.056 (3)	0.032 (2)	−0.004 (2)	0.008 (2)	−0.007 (2)
O43	0.064 (3)	0.043 (2)	0.036 (2)	0.0057 (19)	0.0155 (18)	0.0007 (18)
C163	0.091 (5)	0.045 (4)	0.053 (4)	0.005 (4)	0.022 (4)	0.000 (3)
C183	0.044 (3)	0.049 (4)	0.030 (3)	0.014 (2)	0.012 (2)	0.009 (2)
O53	0.087 (3)	0.048 (3)	0.042 (2)	0.013 (2)	0.005 (2)	0.007 (2)
O63	0.076 (3)	0.051 (3)	0.0263 (19)	0.012 (2)	0.0092 (18)	0.0044 (19)
C193	0.105 (6)	0.059 (5)	0.030 (3)	0.024 (4)	0.015 (3)	0.011 (3)
N14	0.035 (2)	0.042 (3)	0.039 (2)	0.0004 (18)	0.0032 (18)	−0.001 (2)
O14	0.043 (2)	0.042 (3)	0.065 (3)	−0.0072 (18)	−0.0091 (19)	0.011 (2)
O24	0.054 (2)	0.051 (3)	0.057 (3)	0.008 (2)	0.023 (2)	0.013 (2)
O34	0.094 (4)	0.075 (4)	0.076 (4)	0.034 (3)	0.050 (3)	0.017 (3)
N15	0.065 (3)	0.047 (3)	0.035 (3)	−0.021 (3)	0.011 (2)	−0.005 (2)
O15	0.059 (3)	0.052 (3)	0.067 (3)	−0.014 (2)	0.011 (2)	−0.020 (3)
O25	0.095 (4)	0.055 (4)	0.084 (4)	0.009 (3)	0.024 (3)	0.002 (3)
O35	0.080 (4)	0.122 (7)	0.098 (5)	−0.047 (4)	0.013 (4)	−0.046 (5)
N16	0.092 (4)	0.046 (3)	0.049 (3)	−0.020 (3)	−0.003 (3)	0.003 (3)
C16	0.067 (4)	0.037 (3)	0.035 (3)	−0.003 (3)	0.008 (3)	−0.002 (2)
C26	0.065 (4)	0.045 (4)	0.039 (3)	0.002 (3)	−0.001 (3)	−0.008 (3)
N17	0.109 (7)	0.27 (2)	0.068 (6)	0.096 (11)	0.011 (5)	0.028 (9)
C17	0.064 (5)	0.157 (12)	0.046 (4)	0.015 (6)	0.001 (4)	0.027 (6)
C27	0.064 (4)	0.098 (7)	0.054 (4)	−0.011 (4)	−0.004 (3)	0.013 (5)
N18	0.093 (6)	0.057 (5)	0.123 (8)	0.008 (4)	0.013 (5)	−0.004 (5)
C18	0.077 (5)	0.063 (6)	0.077 (6)	0.014 (4)	−0.005 (4)	−0.023 (5)
C28	0.101 (7)	0.070 (7)	0.113 (9)	0.022 (6)	0.005 (6)	−0.013 (6)

Geometric parameters (Å, º) top

Zn—O12	2.058 (3)	C122—H122	0.9300
Zn—O13	2.066 (4)	C132—C142	1.391 (8)
Zn—N13	2.128 (4)	C132—C182	1.494 (8)
Zn—O11	2.130 (4)	C142—H142	0.9300
Zn—N11	2.134 (4)	C152—O32	1.215 (7)
Zn—N12	2.174 (5)	C152—O42	1.339 (7)
N11—C11	1.342 (7)	O42—C162	1.436 (9)
N11—C51	1.343 (7)	C162—H16D	0.9600
C11—C21	1.373 (8)	C162—H16E	0.9600
C11—H11	0.9300	C162—H16F	0.9600
C21—C31	1.391 (10)	C182—O52	1.183 (9)
C21—H21	0.9300	C182—O62	1.335 (8)
C31—C41	1.377 (9)	O62—C192	1.440 (8)
C31—H31	0.9300	C192—H19D	0.9600
C41—C51	1.405 (7)	C192—H19E	0.9600
C41—H41	0.9300	C192—H19F	0.9600
C51—N21	1.391 (7)	N13—C53	1.343 (6)
N21—C61	1.353 (7)	N13—C13	1.348 (7)
N21—H21N	0.90 (7)	C13—C23	1.376 (8)
C61—O11	1.229 (7)	C13—H13	0.9300
C61—C71	1.525 (8)	C23—C33	1.391 (8)
C71—N31	1.454 (7)	C23—H23	0.9300
C71—C711	1.508 (11)	C33—C43	1.375 (8)
C71—H71	0.9800	C33—H33	0.9300
C711—H71A	0.9600	C43—C53	1.396 (7)
C711—H71B	0.9600	C43—H43	0.9300
C711—H71C	0.9600	C53—N23	1.401 (7)
N31—C81	1.333 (8)	N23—C63	1.352 (6)
N31—H31N	0.74 (9)	N23—H23N	0.77 (7)
C81—O21	1.224 (7)	C63—O13	1.234 (6)
C81—C91	1.513 (7)	C63—C73	1.524 (7)
C91—C141	1.391 (8)	C73—N33	1.466 (7)
C91—C101	1.391 (9)	C73—C713	1.521 (9)
C101—C111	1.397 (8)	C73—H73	0.9800
C101—H101	0.9300	C713—H71G	0.9600
C111—C121	1.388 (9)	C713—H71H	0.9600
C111—C151	1.481 (10)	C713—H71I	0.9600
C121—C131	1.381 (9)	N33—C83	1.337 (8)
C121—H121	0.9300	N33—H33N	0.92 (16)
C131—C141	1.403 (8)	C83—O23	1.220 (7)
C131—C181	1.492 (8)	C83—C93	1.513 (7)
C141—H141	0.9300	C93—C103	1.384 (8)
C151—O31	1.204 (9)	C93—C143	1.386 (8)
C151—O41	1.330 (9)	C103—C113	1.394 (8)
O41—C161	1.451 (10)	C103—H103	0.9300
C161—H16A	0.9600	C113—C123	1.388 (8)
C161—H16B	0.9600	C113—C153	1.476 (10)
C161—H16C	0.9600	C123—C133	1.393 (10)
C181—O51	1.237 (8)	C123—H123	0.9300
C181—O61	1.308 (9)	C133—C143	1.393 (8)
O61—C191	1.453 (9)	C133—C183	1.490 (8)
C191—H19A	0.9600	C143—H143	0.9300
C191—H19B	0.9600	C153—O33	1.211 (8)
C191—H19C	0.9600	C153—O43	1.353 (8)
N12—C12	1.346 (7)	O43—C163	1.426 (10)
N12—C52	1.349 (7)	C163—H16G	0.9600
C12—C22	1.380 (9)	C163—H16H	0.9600
C12—H12	0.9300	C163—H16I	0.9600
C22—C32	1.395 (10)	C183—O53	1.189 (9)
C22—H22	0.9300	C183—O63	1.346 (8)
C32—C42	1.374 (8)	O63—C193	1.449 (8)
C32—H32	0.9300	C193—H19G	0.9600
C42—C52	1.398 (8)	C193—H19H	0.9600
C42—H42	0.9300	C193—H19I	0.9600
C52—N22	1.400 (6)	N14—O34	1.225 (8)
N22—C62	1.353 (7)	N14—O14	1.252 (7)
N22—H22N	0.98 (7)	N14—O24	1.262 (7)
C62—O12	1.240 (6)	N15—O25	1.228 (9)
C62—C72	1.516 (6)	N15—O35	1.230 (8)
C72—N32	1.453 (6)	N15—O15	1.248 (8)
C72—C712	1.531 (7)	N16—C16	1.141 (9)
C72—H72	0.9800	C16—C26	1.450 (9)
C712—H71D	0.9600	C26—H26A	0.9600
C712—H71E	0.9600	C26—H26B	0.9600
C712—H71F	0.9600	C26—H26C	0.9600
N32—C82	1.349 (7)	N17—C17	1.130 (19)
N32—H32N	0.87 (6)	C17—C27	1.440 (17)
C82—O22	1.228 (7)	C27—H27A	0.9600
C82—C92	1.498 (7)	C27—H27B	0.9600
C92—C102	1.385 (8)	C27—H27C	0.9600
C92—C142	1.399 (7)	N18—C18	1.133 (14)
C102—C112	1.403 (7)	C18—C28	1.459 (17)
C102—H102	0.9300	C28—H28A	0.9600
C112—C122	1.391 (7)	C28—H28B	0.9600
C112—C152	1.477 (8)	C28—H28C	0.9600
C122—C132	1.380 (8)

O12—Zn—O13	178.36 (17)	C92—C102—H102	120.1
O12—Zn—N13	93.15 (15)	C112—C102—H102	120.1
O13—Zn—N13	85.72 (15)	C122—C112—C102	119.9 (5)
O12—Zn—O11	90.60 (15)	C122—C112—C152	117.9 (5)
O13—Zn—O11	90.47 (15)	C102—C112—C152	122.2 (5)
N13—Zn—O11	84.80 (16)	C132—C122—C112	120.1 (5)
O12—Zn—N11	90.11 (15)	C132—C122—H122	119.9
O13—Zn—N11	91.23 (15)	C112—C122—H122	119.9
N13—Zn—N11	168.71 (18)	C122—C132—C142	120.2 (5)
O11—Zn—N11	84.36 (16)	C122—C132—C182	121.9 (5)
O12—Zn—N12	84.93 (16)	C142—C132—C182	117.9 (5)
O13—Zn—N12	93.99 (16)	C132—C142—C92	120.1 (5)
N13—Zn—N12	95.02 (17)	C132—C142—H142	120.0
O11—Zn—N12	175.52 (16)	C92—C142—H142	120.0
N11—Zn—N12	96.03 (17)	O32—C152—O42	123.5 (6)
C11—N11—C51	117.6 (4)	O32—C152—C112	124.1 (5)
C11—N11—Zn	118.2 (4)	O42—C152—C112	112.4 (5)
C51—N11—Zn	123.9 (3)	C152—O42—C162	115.9 (5)
N11—C11—C21	123.6 (6)	O42—C162—H16D	109.5
N11—C11—H11	118.2	O42—C162—H16E	109.5
C21—C11—H11	118.2	H16D—C162—H16E	109.5
C11—C21—C31	118.7 (5)	O42—C162—H16F	109.5
C11—C21—H21	120.6	H16D—C162—H16F	109.5
C31—C21—H21	120.6	H16E—C162—H16F	109.5
C41—C31—C21	119.0 (5)	O52—C182—O62	123.3 (6)
C41—C31—H31	120.5	O52—C182—C132	125.3 (6)
C21—C31—H31	120.5	O62—C182—C132	111.4 (5)
C31—C41—C51	118.7 (5)	C182—O62—C192	116.0 (6)
C31—C41—H41	120.7	O62—C192—H19D	109.5
C51—C41—H41	120.7	O62—C192—H19E	109.5
N11—C51—N21	120.8 (4)	H19D—C192—H19E	109.5
N11—C51—C41	122.4 (5)	O62—C192—H19F	109.5
N21—C51—C41	116.8 (5)	H19D—C192—H19F	109.5
C61—N21—C51	128.9 (5)	H19E—C192—H19F	109.5
C61—N21—H21N	113 (4)	C53—N13—C13	118.0 (4)
C51—N21—H21N	116 (4)	C53—N13—Zn	124.2 (3)
O11—C61—N21	125.5 (5)	C13—N13—Zn	117.5 (3)
O11—C61—C71	121.8 (5)	N13—C13—C23	123.4 (5)
N21—C61—C71	112.5 (5)	N13—C13—H13	118.3
C61—O11—Zn	122.3 (3)	C23—C13—H13	118.3
N31—C71—C711	109.9 (5)	C13—C23—C33	118.3 (5)
N31—C71—C61	111.7 (5)	C13—C23—H23	120.8
C711—C71—C61	108.4 (6)	C33—C23—H23	120.8
N31—C71—H71	108.9	C43—C33—C23	119.0 (5)
C711—C71—H71	108.9	C43—C33—H33	120.5
C61—C71—H71	108.9	C23—C33—H33	120.5
C71—C711—H71A	109.5	C33—C43—C53	119.4 (5)
C71—C711—H71B	109.5	C33—C43—H43	120.3
H71A—C711—H71B	109.5	C53—C43—H43	120.3
C71—C711—H71C	109.5	N13—C53—C43	121.8 (5)
H71A—C711—H71C	109.5	N13—C53—N23	120.8 (4)
H71B—C711—H71C	109.5	C43—C53—N23	117.4 (4)
C81—N31—C71	119.2 (5)	C63—N23—C53	129.4 (4)
C81—N31—H31N	135 (6)	C63—N23—H23N	117 (5)
C71—N31—H31N	105 (6)	C53—N23—H23N	113 (5)
O21—C81—N31	121.7 (5)	O13—C63—N23	124.9 (5)
O21—C81—C91	120.2 (5)	O13—C63—C73	120.3 (4)
N31—C81—C91	118.1 (5)	N23—C63—C73	114.8 (4)
C141—C91—C101	120.2 (5)	C63—O13—Zn	125.1 (3)
C141—C91—C81	122.4 (5)	N33—C73—C713	110.3 (5)
C101—C91—C81	117.2 (5)	N33—C73—C63	109.1 (5)
C91—C101—C111	119.8 (6)	C713—C73—C63	108.4 (5)
C91—C101—H101	120.1	N33—C73—H73	109.7
C111—C101—H101	120.1	C713—C73—H73	109.7
C121—C111—C101	119.8 (6)	C63—C73—H73	109.7
C121—C111—C151	118.4 (6)	C73—C713—H71G	109.5
C101—C111—C151	121.7 (6)	C73—C713—H71H	109.5
C131—C121—C111	120.6 (5)	H71G—C713—H71H	109.5
C131—C121—H121	119.7	C73—C713—H71I	109.5
C111—C121—H121	119.7	H71G—C713—H71I	109.5
C121—C131—C141	119.8 (5)	H71H—C713—H71I	109.5
C121—C131—C181	119.6 (5)	C83—N33—C73	117.6 (5)
C141—C131—C181	120.6 (6)	C83—N33—H33N	126 (10)
C91—C141—C131	119.7 (5)	C73—N33—H33N	117 (10)
C91—C141—H141	120.1	O23—C83—N33	122.5 (5)
C131—C141—H141	120.1	O23—C83—C93	121.1 (5)
O31—C151—O41	123.6 (7)	N33—C83—C93	116.4 (5)
O31—C151—C111	124.5 (7)	C103—C93—C143	120.4 (5)
O41—C151—C111	111.8 (6)	C103—C93—C83	116.0 (5)
C151—O41—C161	117.2 (7)	C143—C93—C83	123.5 (5)
O41—C161—H16A	109.5	C93—C103—C113	120.5 (5)
O41—C161—H16B	109.5	C93—C103—H103	119.8
H16A—C161—H16B	109.5	C113—C103—H103	119.8
O41—C161—H16C	109.5	C123—C113—C103	119.0 (6)
H16A—C161—H16C	109.5	C123—C113—C153	119.5 (5)
H16B—C161—H16C	109.5	C103—C113—C153	121.5 (5)
O51—C181—O61	123.4 (6)	C113—C123—C133	120.8 (5)
O51—C181—C131	122.1 (6)	C113—C123—H123	119.6
O61—C181—C131	114.5 (5)	C133—C123—H123	119.6
C181—O61—C191	116.1 (6)	C143—C133—C123	119.7 (5)
O61—C191—H19A	109.5	C143—C133—C183	117.9 (6)
O61—C191—H19B	109.5	C123—C133—C183	122.3 (5)
H19A—C191—H19B	109.5	C93—C143—C133	119.6 (6)
O61—C191—H19C	109.5	C93—C143—H143	120.2
H19A—C191—H19C	109.5	C133—C143—H143	120.2
H19B—C191—H19C	109.5	O33—C153—O43	123.6 (7)
C12—N12—C52	117.7 (5)	O33—C153—C113	124.4 (6)
C12—N12—Zn	116.7 (4)	O43—C153—C113	111.9 (5)
C52—N12—Zn	125.6 (3)	C153—O43—C163	117.1 (6)
N12—C12—C22	123.3 (6)	O43—C163—H16G	109.5
N12—C12—H12	118.4	O43—C163—H16H	109.5
C22—C12—H12	118.4	H16G—C163—H16H	109.5
C12—C22—C32	118.6 (5)	O43—C163—H16I	109.5
C12—C22—H22	120.7	H16G—C163—H16I	109.5
C32—C22—H22	120.7	H16H—C163—H16I	109.5
C42—C32—C22	118.9 (6)	O53—C183—O63	123.9 (6)
C42—C32—H32	120.5	O53—C183—C133	124.7 (6)
C22—C32—H32	120.5	O63—C183—C133	111.4 (6)
C32—C42—C52	119.2 (5)	C183—O63—C193	116.4 (6)
C32—C42—H42	120.4	O63—C193—H19G	109.5
C52—C42—H42	120.4	O63—C193—H19H	109.5
N12—C52—C42	122.2 (5)	H19G—C193—H19H	109.5
N12—C52—N22	121.2 (5)	O63—C193—H19I	109.5
C42—C52—N22	116.6 (5)	H19G—C193—H19I	109.5
C62—N22—C52	129.5 (4)	H19H—C193—H19I	109.5
C62—N22—H22N	118 (4)	O34—N14—O14	122.2 (6)
C52—N22—H22N	112 (4)	O34—N14—O24	119.3 (6)
O12—C62—N22	125.0 (4)	O14—N14—O24	118.5 (5)
O12—C62—C72	118.8 (4)	O25—N15—O35	121.9 (7)
N22—C62—C72	116.1 (4)	O25—N15—O15	120.5 (6)
C62—O12—Zn	129.2 (3)	O35—N15—O15	117.6 (7)
N32—C72—C62	108.3 (4)	N16—C16—C26	178.4 (8)
N32—C72—C712	111.2 (4)	C16—C26—H26A	109.5
C62—C72—C712	108.0 (4)	C16—C26—H26B	109.5
N32—C72—H72	109.8	H26A—C26—H26B	109.5
C62—C72—H72	109.8	C16—C26—H26C	109.5
C712—C72—H72	109.8	H26A—C26—H26C	109.5
C72—C712—H71D	109.5	H26B—C26—H26C	109.5
C72—C712—H71E	109.5	N17—C17—C27	179.4 (13)
H71D—C712—H71E	109.5	C17—C27—H27A	109.5
C72—C712—H71F	109.5	C17—C27—H27B	109.5
H71D—C712—H71F	109.5	H27A—C27—H27B	109.5
H71E—C712—H71F	109.5	C17—C27—H27C	109.5
C82—N32—C72	120.6 (4)	H27A—C27—H27C	109.5
C82—N32—H32N	118 (4)	H27B—C27—H27C	109.5
C72—N32—H32N	122 (4)	N18—C18—C28	176.6 (12)
O22—C82—N32	123.4 (5)	C18—C28—H28A	109.5
O22—C82—C92	121.0 (5)	C18—C28—H28B	109.5
N32—C82—C92	115.5 (5)	H28A—C28—H28B	109.5
C102—C92—C142	119.7 (5)	C18—C28—H28C	109.5
C102—C92—C82	122.2 (5)	H28A—C28—H28C	109.5
C142—C92—C82	118.0 (5)	H28B—C28—H28C	109.5
C92—C102—C112	119.9 (5)

C51—N11—C11—C21	−0.5 (9)	O22—C82—C92—C142	34.0 (7)
Zn—N11—C11—C21	173.8 (5)	N32—C82—C92—C142	−147.9 (5)
N11—C11—C21—C31	−0.9 (10)	C142—C92—C102—C112	0.4 (7)
C11—C21—C31—C41	1.9 (10)	C82—C92—C102—C112	178.1 (4)
C21—C31—C41—C51	−1.5 (9)	C92—C102—C112—C122	−0.5 (7)
C11—N11—C51—N21	−179.6 (5)	C92—C102—C112—C152	178.1 (4)
Zn—N11—C51—N21	6.4 (7)	C102—C112—C122—C132	0.9 (7)
C11—N11—C51—C41	0.9 (8)	C152—C112—C122—C132	−177.8 (5)
Zn—N11—C51—C41	−173.1 (4)	C112—C122—C132—C142	−1.2 (7)
C31—C41—C51—N11	0.1 (9)	C112—C122—C132—C182	178.8 (5)
C31—C41—C51—N21	−179.4 (5)	C122—C132—C142—C92	1.1 (7)
N11—C51—N21—C61	21.5 (9)	C182—C132—C142—C92	−179.0 (5)
C41—C51—N21—C61	−159.0 (6)	C102—C92—C142—C132	−0.7 (7)
C51—N21—C61—O11	−9.6 (10)	C82—C92—C142—C132	−178.5 (4)
C51—N21—C61—C71	165.7 (6)	C122—C112—C152—O32	2.7 (8)
N21—C61—O11—Zn	−28.1 (7)	C102—C112—C152—O32	−175.9 (5)
C71—C61—O11—Zn	157.0 (4)	C122—C112—C152—O42	−178.7 (5)
O11—C61—C71—N31	−35.0 (8)	C102—C112—C152—O42	2.7 (7)
N21—C61—C71—N31	149.5 (5)	O32—C152—O42—C162	−0.2 (9)
O11—C61—C71—C711	86.3 (8)	C112—C152—O42—C162	−178.8 (6)
N21—C61—C71—C711	−89.2 (7)	C122—C132—C182—O52	−174.4 (7)
C711—C71—N31—C81	−177.5 (7)	C142—C132—C182—O52	5.6 (10)
C61—C71—N31—C81	−57.1 (7)	C122—C132—C182—O62	6.3 (8)
C71—N31—C81—O21	9.1 (8)	C142—C132—C182—O62	−173.7 (5)
C71—N31—C81—C91	−169.1 (5)	O52—C182—O62—C192	−1.2 (10)
O21—C81—C91—C141	−153.8 (5)	C132—C182—O62—C192	178.1 (6)
N31—C81—C91—C141	24.5 (7)	C53—N13—C13—C23	−1.4 (8)
O21—C81—C91—C101	21.5 (7)	Zn—N13—C13—C23	−174.6 (5)
N31—C81—C91—C101	−160.3 (5)	N13—C13—C23—C33	0.4 (9)
C141—C91—C101—C111	−1.5 (7)	C13—C23—C33—C43	0.6 (9)
C81—C91—C101—C111	−176.9 (4)	C23—C33—C43—C53	−0.5 (8)
C91—C101—C111—C121	−0.3 (7)	C13—N13—C53—C43	1.4 (8)
C91—C101—C111—C151	177.4 (5)	Zn—N13—C53—C43	174.1 (4)
C101—C111—C121—C131	2.0 (8)	C13—N13—C53—N23	−178.6 (5)
C151—C111—C121—C131	−175.8 (5)	Zn—N13—C53—N23	−5.9 (7)
C111—C121—C131—C141	−1.8 (8)	C33—C43—C53—N13	−0.5 (8)
C111—C121—C131—C181	177.5 (5)	C33—C43—C53—N23	179.5 (5)
C101—C91—C141—C131	1.8 (7)	N13—C53—N23—C63	−15.6 (8)
C81—C91—C141—C131	176.9 (5)	C43—C53—N23—C63	164.4 (5)
C121—C131—C141—C91	−0.1 (7)	C53—N23—C63—O13	5.1 (9)
C181—C131—C141—C91	−179.3 (5)	C53—N23—C63—C73	−177.1 (5)
C121—C111—C151—O31	−3.7 (10)	N23—C63—O13—Zn	26.4 (7)
C101—C111—C151—O31	178.5 (7)	C73—C63—O13—Zn	−151.3 (4)
C121—C111—C151—O41	177.7 (5)	O13—C63—C73—N33	−34.9 (7)
C101—C111—C151—O41	−0.1 (8)	N23—C63—C73—N33	147.2 (5)
O31—C151—O41—C161	4.4 (12)	O13—C63—C73—C713	85.3 (7)
C111—C151—O41—C161	−176.9 (7)	N23—C63—C73—C713	−92.6 (6)
C121—C131—C181—O51	16.3 (8)	C713—C73—N33—C83	−173.4 (5)
C141—C131—C181—O51	−164.5 (6)	C63—C73—N33—C83	−54.4 (6)
C121—C131—C181—O61	−162.8 (5)	C73—N33—C83—O23	−6.4 (8)
C141—C131—C181—O61	16.4 (7)	C73—N33—C83—C93	172.9 (4)
O51—C181—O61—C191	−1.9 (9)	O23—C83—C93—C103	26.8 (7)
C131—C181—O61—C191	177.2 (6)	N33—C83—C93—C103	−152.5 (5)
C52—N12—C12—C22	1.8 (9)	O23—C83—C93—C143	−155.9 (5)
Zn—N12—C12—C22	−176.7 (5)	N33—C83—C93—C143	24.7 (7)
N12—C12—C22—C32	−0.6 (11)	C143—C93—C103—C113	−1.7 (8)
C12—C22—C32—C42	−1.2 (10)	C83—C93—C103—C113	175.6 (4)
C22—C32—C42—C52	1.8 (10)	C93—C103—C113—C123	0.7 (8)
C12—N12—C52—C42	−1.2 (8)	C93—C103—C113—C153	−178.1 (5)
Zn—N12—C52—C42	177.2 (4)	C103—C113—C123—C133	1.0 (7)
C12—N12—C52—N22	−179.1 (5)	C153—C113—C123—C133	179.8 (5)
Zn—N12—C52—N22	−0.7 (7)	C113—C123—C133—C143	−1.7 (7)
C32—C42—C52—N12	−0.6 (9)	C113—C123—C133—C183	178.1 (5)
C32—C42—C52—N22	177.4 (5)	C103—C93—C143—C133	1.0 (7)
N12—C52—N22—C62	−11.6 (8)	C83—C93—C143—C133	−176.1 (4)
C42—C52—N22—C62	170.4 (5)	C123—C133—C143—C93	0.7 (7)
C52—N22—C62—O12	1.6 (9)	C183—C133—C143—C93	−179.1 (4)
C52—N22—C62—C72	178.6 (5)	C123—C113—C153—O33	−2.7 (9)
N22—C62—O12—Zn	21.1 (8)	C103—C113—C153—O33	176.2 (6)
C72—C62—O12—Zn	−155.8 (3)	C123—C113—C153—O43	176.5 (5)
O12—C62—C72—N32	−32.2 (7)	C103—C113—C153—O43	−4.7 (7)
N22—C62—C72—N32	150.6 (5)	O33—C153—O43—C163	−2.4 (9)
O12—C62—C72—C712	88.3 (6)	C113—C153—O43—C163	178.5 (6)
N22—C62—C72—C712	−88.9 (6)	C143—C133—C183—O53	3.9 (8)
C62—C72—N32—C82	−136.6 (5)	C123—C133—C183—O53	−175.9 (6)
C712—C72—N32—C82	104.8 (6)	C143—C133—C183—O63	−176.9 (5)
C72—N32—C82—O22	0.5 (8)	C123—C133—C183—O63	3.3 (7)
C72—N32—C82—C92	−177.5 (4)	O53—C183—O63—C193	−0.1 (9)
O22—C82—C92—C102	−143.8 (5)	C133—C183—O63—C193	−179.3 (5)
N32—C82—C92—C102	34.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N32—H32N···O21	0.87 (6)	2.07 (6)	2.916 (6)	163 (5)
N33—H33N···O51ⁱ	0.92 (16)	2.63 (13)	3.227 (7)	123 (12)
N21—H21N···O14	0.90 (7)	2.68 (7)	3.336 (7)	131 (6)
N21—H21N···O24	0.90 (7)	1.99 (7)	2.888 (7)	176 (7)
N23—H23N···O14ⁱⁱ	0.77 (7)	2.06 (7)	2.835 (6)	176 (6)
N22—H22N···O15	0.98 (7)	1.82 (7)	2.733 (6)	154 (6)
N31—H31N···N16	0.74 (9)	2.39 (9)	3.110 (8)	165 (8)

Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z.

Coordination bonds and angles (Å, °) in (1) top

Bonds		Angles between atoms from ligands	1 and 2	2 and 3
Zn—N11	2.134 (4)	N11—Zn—O11	84.36 (16)
Zn—O11	2.130 (4)	N12—Zn—O12	84.93 (16)
Zn—N12	2.174 (5)	N11—Zn—N12	96.03 (17)
Zn—O12	2.058 (3)	N11—Zn—O12	90.11 (15)
Zn—N13	2.128 (4)	N12—Zn—O11	175.52 (16)
Zn—O13	2.066 (4)	O11—Zn—O12	90.60 (15)
		N13—Zn—O13		85.72 (15)
		N11—Zn—N13		168.71 (18)
		N11—Zn—O13		91.23 (15)
		N12—Zn—N13		95.02 (17)
		N12—Zn—O13		93.99 (16)
		N13—Zn—O11		84.80 (16)
		N13—Zn—O12		93.15 (15)
		O11—Zn—O13		90.47 (15)
		O12—Zn—O13		178.36 (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 2^a
N11—C51—N21—C61	21.5 (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—N31	149.5 (5) (ac)	-150.0 (5) (ac)	-153.1 (5) (ap)
N22—C62—C72—N32	150.6 (5) (ap)	-138.9 (5) (ac)	-138.2 (5) (ac)
N23—C63—C73—N33	147.2 (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—C102	34.3 (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—O42	2.7 (7) (sp)	-6.0 (10) (sp)	-8.1 (10) (sp)
C103—C113—C153—O43	-4.7 (7) (sp)

C141—C131—C181—O61	16.4 (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 interaction			Parameter^a
	Θ (°)	d (Å)	R (Å)	l (Å)	α (°)
1^b
Intramolecular (Figs. 1 and 3b)
Ph1···Ph2	122.5	4.048 (3)	3.4134 (19)	2.177	13.2 (2)
Intermolecular (Fig. 4a)
Ph3···Ph1ⁱ	123.7	4.195 (3)	3.490 (2)	2.328	7.0 (2)
Ph3···Ph2ⁱⁱ	123.2	4.295 (3)	3.5941 (19)	2.351	8.0 (2)

BADGAR^c
Ph1···Ph2 (dimer 1, Fig. 3a)	115.7	3.931 (4)	3.542 (2)	1.705	4.1 (3)
Ph3···Ph4 (dimer 2)	118.6	4.018 (3)	3.527 (2)	1.926	2.9 (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···A	D—H	H···A	D···A	D—H···A
1
Intramolecular (Figs. 1 and 2b)
N32—H32N···O21	0.87 (6)	2.07 (6)	2.916 (6)	163 (5)
Intermolecular
Ligand–ligand (Fig. 3a)
N33—H33N···O51ⁱ	0.92 (16)	2.63 (13)	3.227 (7)	123 (12)
Ligand–anion (Fig. 3b)
N21—H21N···O14	0.90 (7)	2.68 (7)	3.336 (7)	131 (6)
N21—H21N···O24	0.90 (7)	1.99 (7)	2.888 (7)	176 (6)
N23—H23N···O14ⁱⁱⁱ	0.77 (7)	2.06 (7)	2.835 (6)	176 (6)
N22—H22N···O15	0.98 (7)	1.82 (7)	2.733 (6)	154 (6)
Ligand–solvent (Fig. 3b)
N31—H31N···N16	0.74 (9)	2.39 (9)	3.110 (8)	165 (8)

BADGAR intradimer (Fig. 2a)
Dimer 1
N31—H31N···O12	0.86	2.03	2.845 (6)	158
N32—H32N···O11	0.86	2.16	2.964 (6)	156
Dimer 2
N33—H33N···O14	0.86	2.01	2.842 (6)	163
N34—H34N···O13	0.86	2.16	2.971 (6)	157

Symmetry codes: (i) x, y, z-1; (iii) x+1, y, z

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Induction of Λ-helicity in a zinc com­plex with an alanine-appended amino­pyridine ligand

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Induction of Λ-helicity in a zinc complex with an alanine-appended aminopyridine ligand