Bis(2,2′-bipyridine-κ²N,N′)(oxalato-κ²O,O′)zinc(II) penta­hydrate

In the crystal structure of the title compound, [Zn(C₂O₄)(C₁₀H₈N₂)₂]·5H₂O, the Zn atom is coordinated by two O atoms from a bidentate chelating oxalate group and four N atoms from two 2,2′-bipyridine ligands in a distorted octa­hedral arrangement. Neutral mononuclear [Zn(C₂O₄)(C₁₀H₈N₂)₂] units are linked by inter­molecular π–π stacking inter­actions of the aromatic rings and a hydrogen-bonding network of uncoordinated water mol­ecules. The compound is isostructural with the Co analogue, [Co(C₂O₄)(C₁₀H₈N₂)₂]·5H₂O [Šestan, Giester & Perić (2004). Acta Cryst. C60, m595–m597], and very similar to the Cu complex containing 1,10-phenanthroline instead of 2,2′-bipyridine, [Cu(C₂O₄)(C₁₂H₈N₂)₂]·5H₂O [Castillo, Luque & Román (2001). J. Mol. Struct. 570, 181–188].

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.093
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C15    -   C16    ...       1.53 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H24    ..  H27     ..       1.92 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H72    ..  H91     ..       2.11 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           33.37
           From the CIF: _reflns_number_total               7328
           From the CIF: _diffrn_reflns_limit_ max hkl   15.   32.   14.
           From the CIF: _diffrn_reflns_limit_ min hkl  -15.  -32.  -14.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   15.   35.   16.
           Calculated minimum hkl  -15.  -35.  -16.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: Nonius Collect Software (Hooft, 1998); cell refinement: DENZO-SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997), Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Bis(2,2'-bipyridine)(oxalato-O,O')zinc(II) pentahydrate

Crystal data

[Zn(C2O4)(C10H8N2)2]·5H2O	F(000) = 1152
Mr = 555.84	In the IR spectrum of (I) the absorption bands corresponding to the bidentate chelating oxalate ligand are located at: 1721, 1672?cm-1 [νas(CO)], 1421?cm-1 [νs(CO) + ν(CC)], 1283, 907?cm-1 [νs(CO) + δ(OCO)] and 778?cm-1 [δ(OCO) + ν(ZnO)]. The band of medium intensity due to ν(ZnO) is located at 412?cm-1. Other absorptions in the spectrum originate from different vibrations of coordinated 2,2'-bipyridine and uncoordinated water molecules (Nakamoto, 1997).
Monoclinic, P21/c	Dx = 1.532 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.001 (2) Å	Cell parameters from 7450 reflections
b = 22.834 (5) Å	θ = 3.4–33.4°
c = 10.854 (2) Å	µ = 1.08 mm^−1
β = 103.45 (3)°	T = 200 K
V = 2410.7 (8) Å^3	Lath, colourless
Z = 4	0.2 × 0.1 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	7328 independent reflections
Radiation source: fine-focus sealed tube	5698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 18.4 pixels mm^-1	θmax = 33.4°, θmin = 3.4°
ω scans	h = −15→15
Absorption correction: multi-scan (DENZO-SCALEPACK; Otwinowski & Minor, 1997)	k = −32→32
Tmin = 0.84, Tmax = 0.95	l = −14→14
14262 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 0.1838P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
7328 reflections	Δρmax = 0.55 e Å^−3
365 parameters	Δρmin = −0.73 e Å^−3
15 restraints

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.65019 (2)	0.10862 (1)	0.29698 (2)	0.0222 (1)
O1	0.81639 (11)	0.10655 (5)	0.22114 (12)	0.0283 (3)
O2	0.62551 (10)	0.03020 (5)	0.19358 (11)	0.0279 (3)
O3	0.90476 (12)	0.05134 (6)	0.08416 (14)	0.0407 (4)
O4	0.73730 (14)	−0.03612 (6)	0.11092 (18)	0.0598 (6)
N11	0.53207 (12)	0.15760 (6)	0.13197 (13)	0.0232 (3)
N12	0.68715 (12)	0.19863 (6)	0.35913 (13)	0.0246 (3)
N21	0.74926 (13)	0.07334 (6)	0.49601 (14)	0.0286 (4)
N22	0.50336 (13)	0.09411 (6)	0.40611 (14)	0.0269 (4)
C1	0.82436 (15)	0.06101 (7)	0.15037 (16)	0.0247 (4)
C2	0.72028 (15)	0.01362 (7)	0.14951 (16)	0.0280 (4)
C11	0.45329 (15)	0.13389 (7)	0.02205 (16)	0.0280 (5)
C12	0.37440 (16)	0.16739 (8)	−0.07807 (17)	0.0322 (5)
C13	0.37683 (17)	0.22758 (8)	−0.06306 (18)	0.0354 (5)
C14	0.45785 (16)	0.25223 (8)	0.05036 (18)	0.0325 (5)
C15	0.53532 (14)	0.21634 (7)	0.14637 (15)	0.0233 (4)
C16	0.62643 (14)	0.23910 (7)	0.27003 (15)	0.0236 (4)
C17	0.65015 (17)	0.29853 (7)	0.29339 (17)	0.0317 (5)
C18	0.73578 (19)	0.31633 (8)	0.41063 (19)	0.0369 (5)
C19	0.79651 (17)	0.27497 (8)	0.50237 (18)	0.0350 (5)
C21	0.87444 (17)	0.06291 (8)	0.53418 (19)	0.0363 (5)
C22	0.9325 (2)	0.04045 (9)	0.6614 (2)	0.0434 (6)
C23	0.8589 (2)	0.02810 (9)	0.7524 (2)	0.0445 (6)
C24	0.7306 (2)	0.03832 (8)	0.71507 (18)	0.0379 (6)
C25	0.67746 (17)	0.06109 (7)	0.58513 (16)	0.0276 (5)
C26	0.53968 (16)	0.07382 (7)	0.53561 (16)	0.0270 (5)
C27	0.45365 (19)	0.06571 (8)	0.61777 (19)	0.0350 (5)
C28	0.3276 (2)	0.07939 (8)	0.5648 (2)	0.0418 (6)
C29	0.29001 (18)	0.09989 (8)	0.4322 (2)	0.0401 (6)
C110	0.76989 (16)	0.21649 (8)	0.47272 (17)	0.0294 (5)
C210	0.38084 (17)	0.10644 (7)	0.35594 (19)	0.0328 (5)
O5	0.09253 (14)	0.39551 (6)	0.48259 (16)	0.0394 (5)
O6	0.98464 (17)	0.31513 (8)	0.27214 (16)	0.0498 (5)
O7	0.18340 (13)	0.19275 (7)	0.16803 (14)	0.0404 (4)
O8	0.00590 (13)	0.18844 (6)	0.32079 (14)	0.0387 (4)
O9	0.14233 (15)	0.30847 (7)	0.09417 (17)	0.0481 (5)
H11	0.45208	0.09336	0.01337	0.0336*
H12	0.32293	0.14977	−0.15107	0.0386*
H13	0.32623	0.25158	−0.12620	0.0425*
H14	0.45965	0.29264	0.06123	0.0390*
H17	0.61044	0.32619	0.23302	0.0380*
H18	0.75195	0.35600	0.42699	0.0443*
H19	0.85221	0.28635	0.57970	0.0420*
H21	0.93255	0.06962	0.48007	0.0436*
H22	1.02680	0.03383	0.68345	0.0521*
H23	0.89935	0.01379	0.83260	0.0534*
H24	0.67155	0.03163	0.76831	0.0455*
H27	0.48280	0.05216	0.70047	0.0419*
H28	0.26018	0.07626	0.61079	0.0502*
H29	0.19826	0.10901	0.39796	0.0481*
H110	0.80935	0.18822	0.53171	0.0352*
H210	0.35320	0.11919	0.27251	0.0393*
H51	0.132 (2)	0.4211 (8)	0.4541 (19)	0.037 (6)*
H52	0.050 (3)	0.4115 (11)	0.529 (2)	0.064 (8)*
H61	0.987 (3)	0.2831 (9)	0.310 (3)	0.084 (11)*
H62	1.014 (3)	0.3364 (11)	0.336 (2)	0.071 (9)*
H71	0.168 (3)	0.1704 (9)	0.1027 (19)	0.052 (7)*
H72	0.174 (3)	0.2269 (8)	0.131 (2)	0.069 (9)*
H81	0.057 (2)	0.1872 (12)	0.268 (2)	0.068 (9)*
H82	−0.050 (2)	0.1615 (10)	0.291 (2)	0.065 (8)*
H91	0.097 (3)	0.3116 (12)	0.149 (2)	0.062 (8)*
H92	0.104 (2)	0.3106 (12)	0.0175 (16)	0.056 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0176 (1)	0.0200 (1)	0.0291 (1)	0.0015 (1)	0.0058 (1)	0.0012 (1)
O1	0.0194 (4)	0.0239 (6)	0.0435 (7)	−0.0017 (4)	0.0115 (5)	−0.0017 (5)
O2	0.0202 (5)	0.0217 (5)	0.0435 (7)	−0.0014 (4)	0.0110 (5)	−0.0016 (5)
O3	0.0299 (6)	0.0418 (7)	0.0576 (9)	0.0030 (5)	0.0250 (6)	0.0001 (7)
O4	0.0349 (7)	0.0323 (7)	0.1171 (14)	−0.0045 (6)	0.0276 (8)	−0.0301 (8)
N11	0.0176 (5)	0.0218 (6)	0.0302 (7)	−0.0006 (4)	0.0054 (5)	0.0013 (5)
N12	0.0192 (5)	0.0228 (6)	0.0316 (7)	0.0007 (5)	0.0055 (5)	−0.0024 (5)
N21	0.0260 (6)	0.0248 (7)	0.0333 (8)	0.0030 (5)	0.0033 (5)	0.0019 (6)
N22	0.0239 (6)	0.0224 (6)	0.0369 (8)	0.0030 (5)	0.0121 (5)	0.0020 (6)
C1	0.0195 (6)	0.0258 (8)	0.0289 (8)	0.0040 (5)	0.0060 (6)	0.0047 (7)
C2	0.0234 (7)	0.0240 (7)	0.0363 (9)	0.0005 (6)	0.0061 (6)	−0.0031 (7)
C11	0.0232 (7)	0.0266 (8)	0.0335 (9)	−0.0036 (6)	0.0049 (6)	−0.0015 (7)
C12	0.0219 (7)	0.0394 (10)	0.0321 (9)	−0.0037 (6)	−0.0001 (6)	0.0001 (8)
C13	0.0257 (7)	0.0379 (10)	0.0388 (10)	0.0042 (7)	−0.0004 (7)	0.0107 (8)
C14	0.0279 (7)	0.0249 (8)	0.0423 (10)	0.0027 (6)	0.0035 (7)	0.0071 (7)
C15	0.0182 (6)	0.0218 (7)	0.0307 (8)	0.0002 (5)	0.0072 (6)	0.0020 (6)
C16	0.0186 (6)	0.0221 (7)	0.0314 (9)	0.0000 (5)	0.0082 (6)	−0.0006 (6)
C17	0.0327 (8)	0.0215 (8)	0.0405 (10)	−0.0005 (6)	0.0078 (7)	0.0012 (7)
C18	0.0375 (9)	0.0259 (8)	0.0484 (11)	−0.0068 (7)	0.0121 (8)	−0.0108 (8)
C19	0.0284 (8)	0.0368 (9)	0.0386 (10)	−0.0055 (7)	0.0052 (7)	−0.0134 (8)
C21	0.0268 (8)	0.0348 (9)	0.0432 (11)	0.0053 (7)	−0.0003 (7)	0.0006 (8)
C22	0.0375 (9)	0.0360 (10)	0.0486 (12)	0.0077 (8)	−0.0064 (9)	0.0008 (9)
C23	0.0552 (12)	0.0346 (10)	0.0341 (10)	0.0080 (9)	−0.0093 (9)	0.0029 (8)
C24	0.0520 (11)	0.0298 (9)	0.0313 (10)	0.0043 (8)	0.0084 (8)	0.0030 (8)
C25	0.0341 (8)	0.0183 (7)	0.0295 (9)	0.0016 (6)	0.0054 (7)	−0.0001 (6)
C26	0.0325 (8)	0.0179 (7)	0.0330 (9)	−0.0001 (6)	0.0125 (7)	−0.0013 (6)
C27	0.0431 (9)	0.0265 (8)	0.0413 (10)	−0.0045 (7)	0.0218 (8)	0.0000 (8)
C28	0.0420 (10)	0.0309 (9)	0.0630 (14)	−0.0053 (8)	0.0336 (10)	−0.0036 (9)
C29	0.0275 (8)	0.0329 (9)	0.0652 (14)	0.0024 (7)	0.0216 (9)	0.0004 (9)
C110	0.0242 (7)	0.0302 (8)	0.0323 (9)	0.0017 (6)	0.0037 (6)	−0.0032 (7)
C210	0.0247 (7)	0.0302 (9)	0.0451 (11)	0.0035 (6)	0.0117 (7)	0.0034 (8)
O5	0.0331 (6)	0.0301 (7)	0.0599 (10)	0.0003 (5)	0.0207 (6)	0.0016 (6)
O6	0.0509 (9)	0.0479 (9)	0.0528 (10)	−0.0055 (7)	0.0164 (8)	−0.0058 (8)
O7	0.0311 (6)	0.0478 (9)	0.0412 (8)	−0.0009 (6)	0.0062 (6)	−0.0005 (7)
O8	0.0281 (6)	0.0446 (8)	0.0439 (8)	−0.0095 (5)	0.0097 (6)	−0.0055 (6)
O9	0.0402 (8)	0.0585 (10)	0.0466 (10)	−0.0075 (7)	0.0121 (7)	0.0066 (8)

Geometric parameters (Å, º)

Zn1—O1	2.0197 (13)	C14—C15	1.408 (2)
Zn1—O2	2.0972 (13)	C15—C16	1.527 (2)
Zn1—N11	2.2068 (15)	C16—C17	1.391 (2)
Zn1—N12	2.1680 (15)	C17—C18	1.418 (3)
Zn1—N21	2.3026 (16)	C18—C19	1.404 (3)
Zn1—N22	2.1162 (15)	C19—C110	1.385 (3)
O1—C1	1.306 (2)	C21—C22	1.461 (3)
O2—C2	1.2171 (19)	C22—C23	1.391 (3)
O3—C1	1.217 (2)	C23—C24	1.274 (3)
O4—C2	1.236 (2)	C24—C25	1.481 (3)
O5—H52	0.82 (3)	C25—C26	1.388 (2)
O5—H51	0.806 (19)	C26—C27	1.388 (3)
O6—H61	0.84 (2)	C27—C28	1.296 (3)
O6—H62	0.84 (2)	C28—C29	1.477 (3)
O7—H71	0.86 (2)	C29—C210	1.372 (3)
O7—H72	0.872 (19)	C11—H11	0.9300
O8—H81	0.85 (2)	C12—H12	0.9300
O8—H82	0.84 (2)	C13—H13	0.9300
N11—C11	1.378 (2)	C14—H14	0.9300
N11—C15	1.350 (2)	C17—H17	0.9300
N12—C16	1.373 (2)	C18—H18	0.9300
N12—C110	1.377 (2)	C19—H19	0.9300
N21—C25	1.361 (2)	C21—H21	0.9300
N21—C21	1.247 (2)	C22—H22	0.9300
N22—C210	1.252 (2)	C23—H23	0.9300
N22—C26	1.444 (2)	C24—H24	0.9300
O9—H92	0.833 (17)	C27—H27	0.9300
O9—H91	0.83 (3)	C28—H28	0.9300
C1—C2	1.500 (2)	C29—H29	0.9300
C11—C12	1.411 (2)	C110—H110	0.9300
C12—C13	1.384 (3)	C210—H210	0.9300
C13—C14	1.423 (3)
Zn1···O8^i	3.9518 (16)	C19···C15^vii	3.347 (2)
Zn1···H82^i	3.25 (2)	C19···C14^vii	3.599 (3)
O1···O2	2.5510 (17)	C23···O3^iv	3.174 (3)
O1···O8^i	2.7028 (19)	C24···C210^ii	3.516 (3)
O1···N11	3.0168 (18)	C24···C29^ii	3.522 (3)
O1···N12	3.0390 (19)	C25···C28^ii	3.592 (3)
O1···C2	2.384 (2)	C26···C26^ii	3.508 (2)
O2···N11	3.0811 (19)	C27···O2^ii	3.220 (2)
O2···C27^ii	3.220 (2)	C28···O9^vii	3.220 (3)
O2···O1	2.5510 (17)	C28···C25^ii	3.592 (3)
O2···C11	3.248 (2)	C29···C24^ii	3.522 (3)
O2···N22	3.2023 (19)	C29···O9^vii	3.295 (3)
O2···C1	2.259 (2)	C1···H18^xi	3.0300
O3···O5^iii	2.679 (2)	C1···H52^iii	2.93 (3)
O3···O4	2.665 (2)	C1···H22^iv	2.9900
O3···C23^iv	3.174 (3)	C1···H82^i	2.88 (2)
O4···O5^v	2.677 (2)	C2···H22^iv	2.9500
O4···C12^vi	3.190 (2)	C2···H51^v	2.947 (19)
O4···O3	2.665 (2)	C110···C14^vii	3.490 (2)
O4···C11^vi	3.069 (2)	C110···O8^i	3.242 (2)
O5···O7^vii	2.844 (2)	C14···H17	2.7800
O5···O4^viii	2.677 (2)	C17···H14	2.7900
O5···C12^vii	3.363 (2)	C18···H61	3.06 (3)
O5···O3^ix	2.679 (2)	C21···H110	2.9300
O5···O6^x	2.933 (2)	C24···H27	2.4700
O6···O9^i	2.768 (2)	C26···H17^vii	3.1000
O6···O5^i	2.933 (2)	C27···H17^vii	3.0300
O6···O8^i	2.940 (2)	C27···H24	2.5200
O6···C18	3.193 (3)	C29···H92^vii	3.05 (2)
O7···O9	2.764 (2)	C210···C24^ii	3.516 (3)
O7···O5^xi	2.844 (2)	C210···O7	3.173 (2)
O7···O8	2.698 (2)	H11···O4^vi	2.4300
O7···C210	3.173 (2)	H11···O2	2.7100
O8···O9^vii	2.964 (2)	H12···O4^vi	2.7200
O8···O7	2.698 (2)	H13···O7^xi	2.6800
O8···O1^x	2.7028 (19)	H14···H17	2.2400
O8···C110^x	3.242 (2)	H14···C17	2.7900
O8···Zn1^x	3.9518 (16)	H17···H14	2.2400
O8···O6^x	2.940 (2)	H17···C26^xi	3.1000
O9···C29^xi	3.295 (3)	H17···C14	2.7800
O9···O8^xi	2.964 (2)	H17···C27^xi	3.0300
O9···O7	2.764 (2)	H18···O3^vii	2.9200
O9···O6^x	2.768 (2)	H18···C1^vii	3.0300
O9···C28^xi	3.220 (3)	H19···H82^xiv	2.5700
O1···H82^i	1.86 (2)	H19···O8^xiv	2.7700
O1···H21	2.9100	H21···O1	2.9100
O2···H27^ii	2.5700	H22···C1^iv	2.9900
O2···H11	2.7100	H22···C2^iv	2.9500
O3···H52^iii	1.90 (3)	H22···O4^iv	2.8500
O3···H23^iv	2.4600	H23···O3^iv	2.4600
O3···H18^xi	2.9200	H23···O3^xv	2.8500
O3···H23^xii	2.8500	H24···C27	2.5200
O4···H22^iv	2.8500	H24···H27	1.9200
O4···H51^v	1.90 (2)	H27···C24	2.4700
O4···H12^vi	2.7200	H27···H24	1.9200
O4···H11^vi	2.4300	H27···O2^ii	2.5700
O5···H62^x	2.10 (2)	H28···O9^vii	2.8700
O5···H71^vii	2.02 (2)	H29···H92^vii	2.5500
O6···H110^xi	2.7900	H29···H81	2.5000
O6···H91^i	1.94 (3)	H29···O8	2.6300
O7···H91	2.84 (3)	H51···C2^viii	2.947 (19)
O7···H81	1.85 (2)	H51···H62^x	2.46 (3)
O7···H210	2.4700	H51···O4^viii	1.90 (2)
O7···H13^vii	2.6800	H52···O3^ix	1.90 (3)
O8···H92^vii	2.132 (17)	H52···H71^vii	2.26 (3)
O8···H19^xiii	2.7700	H52···C1^ix	2.93 (3)
O8···H61^x	2.17 (2)	H61···C18	3.06 (3)
O8···H29	2.6300	H61···H91^i	2.36 (4)
O9···H72	1.916 (19)	H61···H81^i	2.38 (3)
O9···H28^xi	2.8700	H61···O8^i	2.17 (2)
N11···O1	3.0168 (18)	H62···H91^i	2.43 (3)
N11···N12	2.754 (2)	H62···H51^i	2.46 (3)
N11···C16	2.438 (2)	H62···O5^i	2.10 (2)
N11···O2	3.0811 (19)	H71···O5^xi	2.02 (2)
N11···C210	3.357 (2)	H71···H52^xi	2.26 (3)
N12···N11	2.754 (2)	H71···H210	2.5700
N12···C15	2.484 (2)	H71···H81	2.35 (3)
N12···N22	3.126 (2)	H72···H91	2.11 (3)
N12···O1	3.0390 (19)	H72···O9	1.916 (19)
N12···N21	3.217 (2)	H72···H92	2.29 (3)
N21···C26	2.235 (2)	H72···H81	2.28 (3)
N21···N12	3.217 (2)	H81···H71	2.35 (3)
N21···C110	3.289 (2)	H81···H72	2.28 (3)
N21···N22	2.472 (2)	H81···H61^x	2.38 (3)
N22···C25	2.409 (2)	H81···H29	2.5000
N22···N12	3.126 (2)	H81···O7	1.85 (2)
N22···N21	2.472 (2)	H82···O1^x	1.86 (2)
N22···O2	3.2023 (19)	H82···C1^x	2.88 (2)
N11···H210	2.7500	H82···H19^xiii	2.5700
N21···H110	2.7000	H82···Zn1^x	3.25 (2)
C11···C18^xi	3.511 (3)	H91···O6^x	1.94 (3)
C11···O4^vi	3.069 (2)	H91···O7	2.84 (3)
C12···O5^xi	3.363 (2)	H91···H72	2.11 (3)
C12···C17^xi	3.457 (3)	H91···H62^x	2.43 (3)
C12···O4^vi	3.190 (2)	H91···H61^x	2.36 (4)
C13···C17^xi	3.498 (3)	H92···O8^xi	2.132 (17)
C13···C16^xi	3.492 (2)	H92···H72	2.29 (3)
C14···C110^xi	3.490 (2)	H92···C29^xi	3.05 (2)
C14···C19^xi	3.599 (3)	H92···H29^xi	2.5500
C15···C19^xi	3.347 (2)	H110···N21	2.7000
C16···C13^vii	3.492 (2)	H110···C21	2.9300
C17···C12^vii	3.457 (3)	H110···O6^vii	2.7900
C17···C13^vii	3.498 (3)	H210···H71	2.5700
C18···O6	3.193 (3)	H210···O7	2.4700
C18···C11^vii	3.511 (3)	H210···N11	2.7500
O1—Zn1—O2	76.56 (5)	C16—C17—C18	119.02 (16)
O1—Zn1—N11	90.98 (6)	C17—C18—C19	121.00 (17)
O1—Zn1—N12	92.99 (6)	C18—C19—C110	117.12 (17)
O1—Zn1—N21	99.14 (6)	N21—C21—C22	121.93 (18)
O1—Zn1—N22	165.57 (6)	C21—C22—C23	125.64 (19)
O2—Zn1—N11	91.39 (6)	C22—C23—C24	113.4 (2)
O2—Zn1—N12	165.09 (6)	C23—C24—C25	118.62 (19)
O2—Zn1—N21	100.06 (6)	C24—C25—C26	123.11 (16)
O2—Zn1—N22	98.93 (6)	N21—C25—C26	108.78 (15)
N11—Zn1—N12	78.02 (6)	N21—C25—C24	128.11 (16)
N11—Zn1—N21	166.18 (6)	N22—C26—C27	127.96 (16)
N11—Zn1—N22	102.91 (6)	N22—C26—C25	116.51 (15)
N12—Zn1—N21	91.99 (6)	C25—C26—C27	115.53 (16)
N12—Zn1—N22	93.70 (6)	C26—C27—C28	111.54 (18)
N21—Zn1—N22	67.87 (6)	C27—C28—C29	120.64 (19)
Zn1—O1—C1	115.27 (10)	C28—C29—C210	124.64 (18)
Zn1—O2—C2	118.06 (11)	N12—C110—C19	122.45 (17)
H51—O5—H52	107 (2)	N11—C11—H11	118.00
H61—O6—H62	98 (3)	C12—C11—H11	118.00
H71—O7—H72	99.9 (19)	C11—C12—H12	121.00
H81—O8—H82	100 (2)	C13—C12—H12	121.00
C11—N11—C15	118.95 (14)	C14—C13—H13	120.00
Zn1—N11—C11	126.42 (11)	C12—C13—H13	120.00
Zn1—N11—C15	114.56 (11)	C15—C14—H14	120.00
Zn1—N12—C110	125.65 (12)	C13—C14—H14	120.00
C16—N12—C110	120.43 (14)	C18—C17—H17	120.00
Zn1—N12—C16	113.80 (11)	C16—C17—H17	120.00
Zn1—N21—C21	123.94 (13)	C19—C18—H18	120.00
Zn1—N21—C25	123.76 (11)	C17—C18—H18	119.00
C21—N21—C25	112.31 (16)	C110—C19—H19	121.00
Zn1—N22—C26	123.02 (11)	C18—C19—H19	121.00
Zn1—N22—C210	117.24 (13)	C22—C21—H21	119.00
C26—N22—C210	119.66 (15)	N21—C21—H21	119.00
H91—O9—H92	121 (2)	C21—C22—H22	117.00
O1—C1—C2	116.16 (14)	C23—C22—H22	117.00
O3—C1—C2	114.73 (15)	C24—C23—H23	123.00
O1—C1—O3	129.12 (16)	C22—C23—H23	123.00
O4—C2—C1	121.00 (15)	C23—C24—H24	121.00
O2—C2—O4	126.89 (16)	C25—C24—H24	121.00
O2—C2—C1	112.08 (14)	C28—C27—H27	124.00
N11—C11—C12	123.95 (15)	C26—C27—H27	124.00
C11—C12—C13	117.17 (16)	C27—C28—H28	120.00
C12—C13—C14	119.06 (17)	C29—C28—H28	120.00
C13—C14—C15	120.98 (16)	C210—C29—H29	118.00
N11—C15—C16	115.67 (14)	C28—C29—H29	118.00
C14—C15—C16	124.43 (15)	N22—C210—C29	115.56 (18)
N11—C15—C14	119.89 (15)	C19—C110—H110	119.00
N12—C16—C17	119.98 (15)	N12—C110—H110	119.00
C15—C16—C17	122.26 (15)	C29—C210—H210	122.00
N12—C16—C15	117.75 (14)	N22—C210—H210	122.00
O2—Zn1—O1—C1	0.35 (11)	Zn1—N12—C16—C15	4.13 (17)
N11—Zn1—O1—C1	−90.85 (12)	Zn1—N12—C16—C17	−175.12 (12)
N12—Zn1—O1—C1	−168.90 (12)	C110—N12—C16—C15	−179.70 (14)
N21—Zn1—O1—C1	98.60 (12)	C110—N12—C16—C17	1.1 (2)
O1—Zn1—O2—C2	8.86 (12)	Zn1—N12—C110—C19	175.29 (13)
N11—Zn1—O2—C2	99.53 (13)	C16—N12—C110—C19	−0.4 (2)
N21—Zn1—O2—C2	−88.23 (13)	Zn1—N21—C21—C22	−179.91 (14)
N22—Zn1—O2—C2	−157.17 (13)	C25—N21—C21—C22	−0.4 (2)
O1—Zn1—N11—C11	89.06 (13)	Zn1—N21—C25—C24	179.91 (14)
O1—Zn1—N11—C15	−94.00 (11)	Zn1—N21—C25—C26	−0.46 (19)
O2—Zn1—N11—C11	12.49 (13)	C21—N21—C25—C24	0.4 (2)
O2—Zn1—N11—C15	−170.57 (11)	C21—N21—C25—C26	179.98 (16)
N12—Zn1—N11—C11	−178.09 (13)	Zn1—N22—C26—C25	−3.2 (2)
N12—Zn1—N11—C15	−1.15 (11)	Zn1—N22—C26—C27	176.41 (14)
N22—Zn1—N11—C11	−87.00 (13)	C210—N22—C26—C25	−179.87 (16)
N22—Zn1—N11—C15	89.94 (11)	C210—N22—C26—C27	−0.3 (3)
O1—Zn1—N12—C16	88.67 (11)	Zn1—N22—C210—C29	−176.13 (13)
O1—Zn1—N12—C110	−87.27 (13)	C26—N22—C210—C29	0.8 (2)
N11—Zn1—N12—C16	−1.70 (10)	O1—C1—C2—O2	14.9 (2)
N11—Zn1—N12—C110	−177.64 (14)	O3—C1—C2—O4	17.1 (3)
N21—Zn1—N12—C16	−172.07 (11)	O1—C1—C2—O4	−163.03 (17)
N21—Zn1—N12—C110	11.99 (13)	O3—C1—C2—O2	−165.08 (16)
N22—Zn1—N12—C16	−104.12 (11)	N11—C11—C12—C13	−0.4 (2)
N22—Zn1—N12—C110	79.94 (13)	C11—C12—C13—C14	0.3 (2)
O1—Zn1—N21—C21	5.22 (15)	C12—C13—C14—C15	0.3 (3)
O1—Zn1—N21—C25	−174.28 (13)	C13—C14—C15—C16	179.13 (15)
O2—Zn1—N21—C21	83.06 (15)	C13—C14—C15—N11	−0.7 (2)
O2—Zn1—N21—C25	−96.44 (13)	N11—C15—C16—C17	173.96 (15)
N12—Zn1—N21—C21	−88.13 (15)	C14—C15—C16—N12	174.87 (15)
N12—Zn1—N21—C25	92.37 (13)	C14—C15—C16—C17	−5.9 (2)
N22—Zn1—N21—C21	178.68 (16)	N11—C15—C16—N12	−5.3 (2)
N22—Zn1—N21—C25	−0.82 (12)	N12—C16—C17—C18	−0.9 (2)
O2—Zn1—N22—C26	99.31 (13)	C15—C16—C17—C18	179.87 (16)
O2—Zn1—N22—C210	−83.91 (13)	C16—C17—C18—C19	0.1 (3)
N11—Zn1—N22—C26	−167.18 (12)	C17—C18—C19—C110	0.5 (3)
N11—Zn1—N22—C210	9.61 (14)	C18—C19—C110—N12	−0.4 (3)
N12—Zn1—N22—C26	−88.63 (13)	N21—C21—C22—C23	0.3 (3)
N12—Zn1—N22—C210	88.15 (13)	C21—C22—C23—C24	0.0 (3)
N21—Zn1—N22—C26	2.01 (12)	C22—C23—C24—C25	0.0 (3)
N21—Zn1—N22—C210	178.80 (14)	C23—C24—C25—N21	−0.2 (3)
Zn1—O1—C1—O3	172.24 (16)	C23—C24—C25—C26	−179.76 (18)
Zn1—O1—C1—C2	−7.68 (18)	N21—C25—C26—C27	−177.54 (15)
Zn1—O2—C2—O4	163.10 (16)	C24—C25—C26—C27	2.1 (2)
Zn1—O2—C2—C1	−14.63 (18)	C24—C25—C26—N22	−178.27 (15)
Zn1—N11—C11—C12	176.76 (12)	N21—C25—C26—N22	2.1 (2)
C15—N11—C11—C12	−0.1 (2)	N22—C26—C27—C28	−0.5 (3)
Zn1—N11—C15—C14	−176.56 (12)	C25—C26—C27—C28	179.03 (16)
Zn1—N11—C15—C16	3.56 (16)	C26—C27—C28—C29	0.8 (3)
C11—N11—C15—C14	0.6 (2)	C27—C28—C29—C210	−0.4 (3)
C11—N11—C15—C16	−179.25 (13)	C28—C29—C210—N22	−0.5 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x+1, −y+1/2, z−1/2; (iv) −x+2, −y, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1, −y, −z; (vii) x, −y+1/2, z+1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) x−1, −y+1/2, z+1/2; (x) x−1, y, z; (xi) x, −y+1/2, z−1/2; (xii) x, y, z−1; (xiii) x−1, −y+1/2, z−1/2; (xiv) x+1, −y+1/2, z+1/2; (xv) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4^viii	0.806 (19)	1.90 (2)	2.677 (2)	163.4 (19)
O5—H52···O3^ix	0.82 (3)	1.90 (3)	2.679 (2)	160 (2)
O6—H61···O8^i	0.84 (2)	2.17 (2)	2.940 (2)	153 (3)
O6—H62···O5^i	0.84 (2)	2.10 (2)	2.933 (2)	174 (2)
O7—H71···O5^xi	0.86 (2)	2.02 (2)	2.844 (2)	161 (3)
O7—H72···O9	0.872 (19)	1.916 (19)	2.764 (2)	164 (2)
O8—H81···O7	0.85 (2)	1.85 (2)	2.698 (2)	172 (2)
O8—H82···O1^x	0.84 (2)	1.86 (2)	2.7028 (19)	176 (2)
O9—H91···O6^x	0.83 (3)	1.94 (3)	2.768 (2)	177 (3)
O9—H92···O8^xi	0.833 (17)	2.132 (17)	2.964 (2)	177 (3)

Symmetry codes: (i) x+1, y, z; (viii) −x+1, y+1/2, −z+1/2; (ix) x−1, −y+1/2, z+1/2; (x) x−1, y, z; (xi) x, −y+1/2, z−1/2.