Poly[dimethyl­ammonium [bis­(dimethyl­amine)tri-μ₄-terephthalato-sodium(I)dizinc(II)]]

The three terephthalate groups in the title polymeric coordination compound, {(C₂H₈N)[NaZn₂(C₈H₄O₄)₃(C₂H₇N)₂]}_n, lie on inversion centers. One functions as a bridge to two Na and two Zn atoms. The O atoms of the other two terephthalate groups bind to only one Zn atom. The Zn atom is additionally coordinated by a dimethyl­amine mol­ecule; together with bonding from the O atoms of the three terephthalate groups, the geometry is tetra­hedral. The manner of bridging of the terephalate groups gives rise to a polyanionic honeycomb sheet motif; the sheets are held into a three-dimensional network through the Na atoms. The cavities in the network are occupied by the dimethyl­ammonium cations. The organic cation is disordered about a centre of inversion.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.133
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.06

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.500     0.764
            Tmin(prime) and Tmax expected:      0.627     0.752
            RR(prime) =      0.785
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         40 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Na1
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         N2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      80.00 A   3 

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         21

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

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

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Related literature

A similar compound, bis(µ₅-terephthalato)(µ₄-terephthalato)bis(dimethyformamide)sodiumzinc, was synthesized by using a conventional preparation; the DMF is incorporated into the crystal structure (see Yang et al., 2002). Under hydrothermal conditions, the DMF is decomposed into dimethylamine, which coordinates to zinc in the title compound.

S1. Experimental

Zinc formate (1.55 g, 1 mmol) and terephthalic acid (1.66 g, 1 mmol) in dissolved in DMF (10 ml). The solution was heated in a 25-ml, Teflon-lined stainless-steel Parr bomb at 433 K for five days. The bomb was allowed to cool to room temperature. Several colorless prisms were picked out by hand.

S2. Refinement

Carbon- and nitrogen-bound H atoms were placed in calculated positions [C—H 0.93–0.97 Å and U_iso(H) 1.2–1.5U_eq(C)], and were included in the refinement in the riding-model approximation.

The dimethylammonium cation is disordered about an inversion site, and was refined as a half-occupancy species, subject to distance restraints of C–N 1.45±01 and C···C 2.37±0.01 Å. Their anisotropic temperature factors were restrained to be nearly isotropic.

The refinement initially assumed two independent zinc atoms in the asymmetric unit; however, the difference Fourier consistently had a deep hole near that atom on the inversion site. The occupancy of the zinc atom at (1/2, 1/2, 1/2) refined to 0.188, an occupancy consistent with sodium. The refinement with magnesium in place of sodium led to worse convergence. Furthermore, the octahedral environment of oxygen atoms at distances of 2.3 to 2.5 Å is consistent with this assumption. Sodium could have come from the water used to clean the containers, or the terephthalic acid was contaminated with unknown amounts of the sodium salt.

The final difference Fourier map had a large peak at 2.66 Å from H13a; this peak could not be refined as an oxygen atom.

Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

	Fig. 1. Thermal ellipsoid plot of a portion of the polymeric structure; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. (Symmetry code is given in Table 1.)
	Fig. 2. Layer structure of the zinc-terepthalate network as illustrated by OLEX (Dolomanov et al., 2003).

Poly[dimethylammonium [bis(dimethylamine)tri-µ₄-terephthalato-sodium(I)dizinc(II)]]

Crystal data

(C2H8N)[NaZn2(C8H4O4)3(C2H7N)2]	Z = 1
Mr = 782.33	F(000) = 402
Triclinic, P1	Dx = 1.461 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7893 (4) Å	Cell parameters from 8042 reflections
b = 10.3641 (4) Å	θ = 3.1–27.5°
c = 10.6649 (4) Å	µ = 1.42 mm^−1
α = 111.801 (1)°	T = 295 K
β = 100.498 (1)°	Prism, colorless
γ = 109.257 (1)°	0.32 × 0.26 × 0.20 mm
V = 889.29 (6) Å^3

Data collection

Rigaku RAXIS-RAPID diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 10.000 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω–scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.500, Tmax = 0.764	l = −13→13
8744 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0891P)^2 + 0.691P] where P = (Fo^2 + 2Fc^2)/3
4032 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 1.52 e Å^−3
21 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.59102 (3)	0.46809 (3)	0.79701 (3)	0.02569 (13)
Na1	0.5000	0.5000	0.5000	0.0244 (3)
O1	0.5534 (4)	0.7060 (3)	0.7200 (3)	0.0504 (6)
O2	0.5491 (3)	0.6447 (2)	0.8990 (2)	0.0373 (5)
O3	0.3246 (3)	0.3460 (3)	0.5606 (3)	0.0487 (6)
O4	0.4059 (2)	0.2685 (3)	0.7140 (3)	0.0442 (5)
O5	0.6919 (2)	0.4596 (3)	0.6530 (2)	0.0385 (5)
O6	0.9088 (3)	0.6470 (3)	0.8285 (3)	0.0530 (6)
N1	0.7009 (3)	0.4443 (3)	0.9649 (3)	0.0379 (6)
H1	0.6297	0.3985	0.9910	0.045*
C1	0.5425 (3)	0.7297 (3)	0.8384 (3)	0.0337 (6)
C2	0.5199 (3)	0.8695 (3)	0.9231 (3)	0.0314 (5)
C3	0.4778 (4)	0.9489 (3)	0.8546 (3)	0.0368 (6)
H3	0.4632	0.9147	0.7572	0.044*
C4	0.5425 (4)	0.9221 (3)	1.0700 (3)	0.0354 (6)
H4	0.5711	0.8703	1.1168	0.042*
C5	0.3034 (3)	0.2560 (3)	0.6121 (3)	0.0357 (6)
C6	0.1461 (4)	0.1213 (4)	0.5529 (4)	0.0409 (7)
C7	0.0188 (4)	0.1272 (4)	0.4790 (5)	0.0598 (11)
H7	0.0311	0.2126	0.4640	0.072*
C8	0.1269 (4)	−0.0070 (5)	0.5731 (5)	0.0597 (11)
H8	0.2121	−0.0127	0.6218	0.072*
C9	0.8376 (3)	0.5484 (4)	0.7029 (3)	0.0352 (6)
C10	0.9209 (3)	0.5225 (3)	0.5965 (3)	0.0307 (5)
C11	0.8412 (3)	0.4176 (4)	0.4516 (4)	0.0367 (6)
H11	0.7345	0.3623	0.4187	0.044*
C12	1.0806 (3)	0.6048 (4)	0.6438 (3)	0.0365 (6)
H12	1.1350	0.6755	0.7405	0.044*
C13	0.7748 (5)	0.3415 (5)	0.9174 (5)	0.0580 (10)
H13A	0.7019	0.2478	0.8332	0.087*
H13B	0.8092	0.3180	0.9929	0.087*
H13C	0.8616	0.3917	0.8952	0.087*
C14	0.8095 (4)	0.5905 (5)	1.0944 (4)	0.0552 (9)
H14A	0.7582	0.6551	1.1234	0.083*
H14B	0.8961	0.6424	1.0730	0.083*
H14C	0.8448	0.5689	1.1711	0.083*
N2	0.972 (2)	0.971 (5)	0.987 (3)	0.208 (10)	0.50
H2A	0.9050	0.8762	0.9352	0.249*	0.50
H2B	0.9252	1.0288	0.9983	0.249*	0.50
C15	1.083 (2)	1.0104 (17)	0.9171 (17)	0.113 (5)	0.50
H15A	1.0303	1.0028	0.8274	0.170*	0.50
H15B	1.1296	0.9404	0.8991	0.170*	0.50
H15C	1.1609	1.1140	0.9785	0.170*	0.50
C16	1.059 (3)	0.994 (2)	1.1262 (18)	0.156 (8)	0.50
H16A	0.9906	0.9761	1.1783	0.235*	0.50
H16B	1.1385	1.0981	1.1802	0.235*	0.50
H16C	1.1050	0.9234	1.1119	0.235*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02318 (18)	0.02679 (19)	0.03174 (19)	0.01195 (14)	0.01341 (13)	0.01542 (14)
Na1	0.0289 (7)	0.0256 (6)	0.0254 (6)	0.0119 (6)	0.0155 (6)	0.0155 (5)
O1	0.0838 (19)	0.0400 (12)	0.0462 (13)	0.0368 (13)	0.0382 (13)	0.0227 (10)
O2	0.0492 (12)	0.0339 (10)	0.0431 (11)	0.0273 (10)	0.0229 (10)	0.0209 (9)
O3	0.0360 (12)	0.0443 (12)	0.0695 (16)	0.0084 (10)	0.0204 (11)	0.0372 (12)
O4	0.0278 (10)	0.0414 (12)	0.0447 (12)	0.0001 (9)	0.0018 (9)	0.0197 (10)
O5	0.0313 (10)	0.0482 (12)	0.0497 (12)	0.0206 (9)	0.0278 (10)	0.0272 (10)
O6	0.0454 (13)	0.0672 (16)	0.0425 (13)	0.0212 (13)	0.0245 (11)	0.0203 (12)
N1	0.0275 (11)	0.0504 (15)	0.0457 (14)	0.0167 (11)	0.0150 (11)	0.0312 (12)
C1	0.0375 (15)	0.0268 (12)	0.0382 (14)	0.0157 (12)	0.0157 (12)	0.0138 (11)
C2	0.0400 (15)	0.0262 (12)	0.0303 (12)	0.0168 (11)	0.0141 (11)	0.0124 (10)
C3	0.0530 (18)	0.0327 (14)	0.0283 (12)	0.0219 (13)	0.0154 (12)	0.0142 (11)
C4	0.0465 (16)	0.0312 (13)	0.0341 (14)	0.0205 (13)	0.0133 (12)	0.0178 (11)
C5	0.0279 (13)	0.0331 (14)	0.0386 (14)	0.0049 (11)	0.0121 (12)	0.0162 (12)
C6	0.0295 (14)	0.0379 (15)	0.0431 (16)	−0.0006 (12)	0.0024 (12)	0.0247 (13)
C7	0.0374 (18)	0.048 (2)	0.088 (3)	0.0028 (16)	0.0022 (18)	0.049 (2)
C8	0.0351 (17)	0.053 (2)	0.079 (3)	0.0040 (16)	−0.0043 (18)	0.043 (2)
C9	0.0346 (14)	0.0458 (16)	0.0438 (15)	0.0244 (13)	0.0245 (13)	0.0279 (14)
C10	0.0281 (13)	0.0396 (14)	0.0397 (14)	0.0192 (12)	0.0204 (11)	0.0254 (12)
C11	0.0251 (12)	0.0440 (16)	0.0494 (16)	0.0160 (12)	0.0203 (12)	0.0257 (14)
C12	0.0286 (14)	0.0452 (16)	0.0389 (14)	0.0165 (13)	0.0169 (12)	0.0200 (13)
C13	0.051 (2)	0.065 (2)	0.086 (3)	0.038 (2)	0.028 (2)	0.049 (2)
C14	0.0416 (18)	0.067 (2)	0.0456 (18)	0.0172 (18)	0.0061 (15)	0.0246 (18)
N2	0.214 (13)	0.208 (15)	0.197 (12)	0.074 (10)	0.097 (10)	0.095 (9)
C15	0.114 (8)	0.088 (7)	0.127 (8)	0.023 (5)	0.066 (7)	0.046 (6)
C16	0.159 (11)	0.128 (10)	0.161 (11)	0.047 (8)	0.053 (9)	0.061 (8)

Geometric parameters (Å, º)

Zn1—O5	1.963 (2)	C6—C8	1.383 (5)
Zn1—O2	1.970 (2)	C7—C8^iii	1.386 (5)
Zn1—O4	1.982 (2)	C7—H7	0.9300
Zn1—N1	2.056 (3)	C8—C7^iii	1.386 (5)
Na1—O3	2.297 (2)	C8—H8	0.9300
Na1—O3^i	2.297 (2)	C9—C10	1.510 (4)
Na1—O1	2.331 (2)	C10—C11	1.390 (4)
Na1—O1^i	2.331 (2)	C10—C12	1.393 (4)
Na1—O5	2.505 (2)	C11—C12^iv	1.378 (4)
Na1—O5^i	2.505 (2)	C11—H11	0.9300
O1—C1	1.226 (4)	C12—C11^iv	1.378 (4)
O2—C1	1.282 (4)	C12—H12	0.9300
O3—C5	1.229 (4)	C13—H13A	0.9600
O4—C5	1.271 (4)	C13—H13B	0.9600
O5—C9	1.288 (4)	C13—H13C	0.9600
O6—C9	1.224 (4)	C14—H14A	0.9600
N1—C13	1.468 (5)	C14—H14B	0.9600
N1—C14	1.477 (5)	C14—H14C	0.9600
N1—H1	0.8600	N2—C15	1.455 (10)
C1—C2	1.509 (4)	N2—C16	1.458 (10)
C2—C3	1.393 (4)	N2—H2A	0.8600
C2—C4	1.400 (4)	N2—H2B	0.8600
C3—C4^ii	1.382 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C3^ii	1.382 (4)	C15—H15C	0.9600
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.514 (4)	C16—H16B	0.9600
C6—C7	1.381 (5)	C16—H16C	0.9600
O5—Zn1—O2	122.49 (9)	C7—C6—C5	119.5 (3)
O5—Zn1—O4	107.71 (10)	C8—C6—C5	121.3 (3)
O2—Zn1—O4	111.96 (10)	C6—C7—C8^iii	120.5 (3)
O5—Zn1—N1	114.27 (10)	C6—C7—H7	119.7
O2—Zn1—N1	101.73 (10)	C8^iii—C7—H7	119.7
O4—Zn1—N1	95.35 (10)	C6—C8—C7^iii	120.2 (3)
O3—Na1—O3^i	180.00 (12)	C6—C8—H8	119.9
O3—Na1—O1	87.36 (10)	C7^iii—C8—H8	119.9
O3^i—Na1—O1	92.64 (10)	O6—C9—O5	123.9 (3)
O3—Na1—O1^i	92.64 (10)	O6—C9—C10	120.2 (3)
O3^i—Na1—O1^i	87.36 (10)	O5—C9—C10	115.8 (3)
O1—Na1—O1^i	180.0	C11—C10—C12	119.0 (3)
O3—Na1—O5	83.95 (8)	C11—C10—C9	121.3 (3)
O3^i—Na1—O5	96.05 (8)	C12—C10—C9	119.7 (3)
O1—Na1—O5	82.33 (9)	C12^iv—C11—C10	120.4 (3)
O1^i—Na1—O5	97.67 (9)	C12^iv—C11—H11	119.8
O3—Na1—O5^i	96.05 (8)	C10—C11—H11	119.8
O3^i—Na1—O5^i	83.95 (8)	C11^iv—C12—C10	120.5 (3)
O1—Na1—O5^i	97.67 (9)	C11^iv—C12—H12	119.7
O1^i—Na1—O5^i	82.33 (9)	C10—C12—H12	119.7
O5—Na1—O5^i	180.0	N1—C13—H13A	109.5
C1—O1—Na1	139.5 (2)	N1—C13—H13B	109.5
C1—O2—Zn1	116.88 (18)	H13A—C13—H13B	109.5
C5—O3—Na1	144.9 (2)	N1—C13—H13C	109.5
C5—O4—Zn1	110.7 (2)	H13A—C13—H13C	109.5
C9—O5—Zn1	115.7 (2)	H13B—C13—H13C	109.5
C9—O5—Na1	121.97 (19)	N1—C14—H14A	109.5
Zn1—O5—Na1	94.39 (8)	N1—C14—H14B	109.5
C13—N1—C14	111.2 (3)	H14A—C14—H14B	109.5
C13—N1—Zn1	111.3 (2)	N1—C14—H14C	109.5
C14—N1—Zn1	115.2 (2)	H14A—C14—H14C	109.5
C13—N1—H1	106.1	H14B—C14—H14C	109.5
C14—N1—H1	106.2	C15—N2—C16	107.3 (10)
Zn1—N1—H1	106.1	C15—N2—H2A	110.3
O1—C1—O2	125.3 (3)	C16—N2—H2A	110.3
O1—C1—C2	118.9 (3)	C15—N2—H2B	110.3
O2—C1—C2	115.7 (2)	C16—N2—H2B	110.3
C3—C2—C4	119.3 (3)	H2A—N2—H2B	108.5
C3—C2—C1	119.6 (3)	N2—C15—H15A	109.5
C4—C2—C1	121.1 (2)	N2—C15—H15B	109.5
C4^ii—C3—C2	120.7 (3)	H15A—C15—H15B	109.5
C4^ii—C3—H3	119.7	N2—C15—H15C	109.5
C2—C3—H3	119.7	H15A—C15—H15C	109.5
C3^ii—C4—C2	120.0 (3)	H15B—C15—H15C	109.5
C3^ii—C4—H4	120.0	N2—C16—H16A	109.5
C2—C4—H4	120.0	N2—C16—H16B	109.5
O3—C5—O4	124.1 (3)	H16A—C16—H16B	109.5
O3—C5—C6	119.0 (3)	N2—C16—H16C	109.5
O4—C5—C6	116.9 (3)	H16A—C16—H16C	109.5
C7—C6—C8	119.3 (3)	H16B—C16—H16C	109.5
O3—Na1—O1—C1	22.2 (4)	Na1—Zn1—N1—C14	92.3 (4)
O3^i—Na1—O1—C1	−157.8 (4)	Na1—O1—C1—O2	29.8 (6)
O5—Na1—O1—C1	−62.1 (4)	Na1—O1—C1—C2	−150.5 (3)
O5^i—Na1—O1—C1	117.9 (4)	Zn1—O2—C1—O1	3.3 (4)
O5—Zn1—O2—C1	22.2 (3)	Zn1—O2—C1—C2	−176.43 (19)
O4—Zn1—O2—C1	−108.0 (2)	O1—C1—C2—C3	14.2 (5)
N1—Zn1—O2—C1	151.2 (2)	O2—C1—C2—C3	−166.0 (3)
O1—Na1—O3—C5	−96.9 (4)	O1—C1—C2—C4	−165.0 (3)
O1^i—Na1—O3—C5	83.1 (4)	O2—C1—C2—C4	14.8 (4)
O5—Na1—O3—C5	−14.4 (4)	C4—C2—C3—C4^ii	−0.3 (5)
O5^i—Na1—O3—C5	165.6 (4)	C1—C2—C3—C4^ii	−179.5 (3)
Zn1—Na1—O3—C5	−40.3 (4)	C3—C2—C4—C3^ii	0.3 (5)
Zn1^i—Na1—O3—C5	139.7 (4)	C1—C2—C4—C3^ii	179.5 (3)
O5—Zn1—O4—C5	−69.6 (2)	Na1—O3—C5—O4	35.7 (6)
O2—Zn1—O4—C5	67.9 (2)	Na1—O3—C5—C6	−144.7 (3)
N1—Zn1—O4—C5	172.8 (2)	Zn1—O4—C5—O3	8.7 (4)
O2—Zn1—O5—C9	73.2 (2)	Zn1—O4—C5—C6	−170.9 (2)
O4—Zn1—O5—C9	−154.8 (2)	O3—C5—C6—C7	−20.8 (5)
N1—Zn1—O5—C9	−50.3 (2)	O4—C5—C6—C7	158.9 (4)
O2—Zn1—O5—Na1	−55.59 (12)	O3—C5—C6—C8	160.1 (4)
O4—Zn1—O5—Na1	76.39 (10)	O4—C5—C6—C8	−20.3 (5)
N1—Zn1—O5—Na1	−179.06 (9)	C8—C6—C7—C8^iii	0.8 (8)
O3—Na1—O5—C9	−162.0 (2)	C5—C6—C7—C8^iii	−178.4 (4)
O3^i—Na1—O5—C9	18.0 (2)	C7—C6—C8—C7^iii	−0.8 (8)
O1—Na1—O5—C9	−73.9 (2)	C5—C6—C8—C7^iii	178.4 (4)
O1^i—Na1—O5—C9	106.1 (2)	Zn1—O5—C9—O6	−8.9 (4)
O3—Na1—O5—Zn1	−37.89 (10)	Na1—O5—C9—O6	104.7 (3)
O3^i—Na1—O5—Zn1	142.11 (10)	Zn1—O5—C9—C10	169.76 (18)
O1—Na1—O5—Zn1	50.25 (9)	Na1—O5—C9—C10	−76.6 (3)
O1^i—Na1—O5—Zn1	−129.75 (9)	O6—C9—C10—C11	−176.2 (3)
O5—Zn1—N1—C13	−33.0 (3)	O5—C9—C10—C11	5.1 (4)
O2—Zn1—N1—C13	−167.0 (2)	O6—C9—C10—C12	3.8 (4)
O4—Zn1—N1—C13	79.2 (2)	O5—C9—C10—C12	−174.9 (3)
Na1—Zn1—N1—C13	−35.5 (4)	C12—C10—C11—C12^iv	0.2 (5)
O5—Zn1—N1—C14	94.8 (3)	C9—C10—C11—C12^iv	−179.8 (3)
O2—Zn1—N1—C14	−39.2 (3)	C11—C10—C12—C11^iv	−0.2 (5)
O4—Zn1—N1—C14	−153.0 (2)	C9—C10—C12—C11^iv	179.8 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x, −y, −z+1; (iv) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^v	0.86	2.29	3.122 (3)	162

Symmetry code: (v) −x+1, −y+1, −z+2.