Poly[piperazinediium [aqua-bis(μ-pyridine-2,5-dicarboxyl-ato)zincate] dihydrate].

The polymeric title compound, {(C(4)H(12)N(2))[Zn(C(7)H(3)NO(4))(2)(H(2)O)]·2H(2)O}(n), was obtained by the reaction of zinc(II) nitrate hexa-hydrate with the proton-transfer compound (pipzH(2))(py-2,5-dc) (where pipz is piperazine and py-2,5-dcH(2) is pyridine-2,5-dicarboxylic acid) in aqueous solution. Each Zn(II) atom is coordinated in a distorted octa-hedral geometry by four O atoms and two N atoms from one water mol-ecule and two (py-2,5-dc)(2-) ligands, which also act as bridging ligands between Zn(II) atoms. π-π Stacking inter-actions between two aromatic rings of (py-2,5-dc)(2-) fragments, with centroid-centroid distances of 3.4747 (7) and 3.7081 (7) Å are observed. The crystal structure is stabilized by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Aghabozorg et al. (2007 ▶, 2007a ▶,b ▶); Sheshmani et al. (2007 ▶).

Experimental

Crystal data

(C4H12N2)[Zn(C7H3NO4)2(H2O)]·2H2O

M = 537.78

Monoclinic,

a = 13.1752 (5) Å

b = 11.9066 (5) Å

c = 13.6902 (5) Å

β = 100.567 (1)°

V = 2111.19 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.24 mm−1

T = 100 (2) K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector’ diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.756, T max = 0.808

26339 measured reflections

6148 independent reflections

5458 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.069

S = 1.03

6148 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2005 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063787/bt2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063787/bt2642Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C4H12N2)[Zn(C7H3N1O4)2(H2O1)]·2H2O	F000 = 1112
Mr = 537.78	Dx = 1.692 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 583 reflections
a = 13.1752 (5) Å	θ = 3–30º
b = 11.9066 (5) Å	µ = 1.24 mm−1
c = 13.6902 (5) Å	T = 100 (2) K
β = 100.5670 (10)º	Prism, colourless
V = 2111.19 (14) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector' diffractometer	6148 independent reflections
Radiation source: fine-focus sealed tube	5458 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 100(2) K	θmax = 30.0º
ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −18→18
Tmin = 0.756, Tmax = 0.808	k = −16→16
26339 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0365P)2 + 1.P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6148 reflections	Δρmax = 0.83 e Å−3
307 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
Zn1	0.157893 (10)	−0.413714 (11)	0.162746 (10)	0.00887 (5)
O1	0.22982 (7)	−0.25877 (8)	0.17492 (7)	0.01233 (17)
O2	0.20008 (9)	−0.07463 (9)	0.15203 (11)	0.0298 (3)
O3	−0.32052 (7)	−0.19745 (8)	0.00316 (8)	0.01648 (19)
O4	−0.28405 (7)	−0.37980 (8)	0.01990 (8)	0.01749 (19)
O5	0.30053 (7)	−0.48325 (7)	0.22242 (7)	0.01115 (17)
O6	0.38201 (7)	−0.64637 (8)	0.26384 (8)	0.0179 (2)
O7	−0.11016 (7)	−0.88980 (8)	0.19126 (7)	0.01188 (17)
O8	−0.17065 (7)	−0.73902 (8)	0.10247 (7)	0.01579 (19)
O9	0.18192 (7)	−0.43941 (8)	0.01814 (7)	0.01400 (18)
H9A	0.1826	−0.3867	−0.0203	0.017*
H9B	0.2171	−0.4917	0.0041	0.017*
N1	0.03069 (8)	−0.30642 (9)	0.10358 (8)	0.00939 (19)
N2	0.11783 (8)	−0.58497 (8)	0.17585 (8)	0.00904 (19)
C1	0.05938 (9)	−0.19776 (10)	0.10974 (9)	0.0110 (2)
C2	−0.01048 (10)	−0.11078 (11)	0.08528 (10)	0.0135 (2)
H2A	0.0123	−0.0349	0.0895	0.016*
C3	−0.11439 (10)	−0.13610 (11)	0.05445 (10)	0.0134 (2)
H3A	−0.1637	−0.0777	0.0380	0.016*
C4	−0.14516 (9)	−0.24797 (10)	0.04793 (9)	0.0103 (2)
C5	−0.06942 (9)	−0.33022 (10)	0.07249 (9)	0.0099 (2)
H5A	−0.0898	−0.4068	0.0669	0.012*
C6	0.17291 (10)	−0.17423 (11)	0.14852 (10)	0.0141 (2)
C7	−0.25825 (9)	−0.27880 (11)	0.02066 (9)	0.0116 (2)
C8	0.20087 (9)	−0.65035 (10)	0.20725 (9)	0.0093 (2)
C9	0.19325 (9)	−0.76566 (10)	0.21772 (9)	0.0109 (2)
H9C	0.2534	−0.8101	0.2377	0.013*
C10	0.09628 (9)	−0.81510 (10)	0.19858 (9)	0.0108 (2)
H10A	0.0892	−0.8938	0.2064	0.013*
C11	0.00939 (9)	−0.74839 (10)	0.16771 (9)	0.0094 (2)
C12	0.02468 (9)	−0.63331 (10)	0.15639 (9)	0.0100 (2)
H12A	−0.0338	−0.5873	0.1338	0.012*
C13	0.30435 (9)	−0.59080 (10)	0.23404 (9)	0.0104 (2)
C14	−0.09852 (9)	−0.79664 (10)	0.15208 (9)	0.0101 (2)
N3	0.35861 (8)	−0.31370 (9)	0.36536 (8)	0.0119 (2)
H3B	0.2960	−0.2863	0.3754	0.014*
H3C	0.3469	−0.3564	0.3084	0.014*
N4	0.49509 (8)	−0.22071 (9)	0.53234 (8)	0.0123 (2)
H4A	0.5059	−0.1777	0.5892	0.015*
H4B	0.5580	−0.2480	0.5233	0.015*
C15	0.42751 (10)	−0.21754 (11)	0.35168 (10)	0.0149 (2)
H15A	0.3933	−0.1696	0.2962	0.018*
H15B	0.4926	−0.2463	0.3347	0.018*
C16	0.45104 (10)	−0.14881 (11)	0.44632 (10)	0.0150 (2)
H16A	0.5008	−0.0886	0.4384	0.018*
H16B	0.3869	−0.1129	0.4588	0.018*
C17	0.42647 (10)	−0.31659 (11)	0.54554 (10)	0.0136 (2)
H17A	0.3609	−0.2879	0.5616	0.016*
H17B	0.4602	−0.3642	0.6014	0.016*
C18	0.40415 (10)	−0.38587 (11)	0.45105 (10)	0.0135 (2)
H18A	0.4689	−0.4202	0.4384	0.016*
H18B	0.3555	−0.4471	0.4589	0.016*
O1W	0.37141 (7)	0.04431 (8)	0.14623 (7)	0.01687 (19)
H1WA	0.3491	0.0939	0.1065	0.020*
H1WB	0.3222	0.0028	0.1486	0.020*
O2W	0.50510 (8)	0.07757 (9)	0.31667 (8)	0.0206 (2)
H2WA	0.4610	0.0668	0.2669	0.025*
H2WB	0.5594	0.0516	0.3052	0.025*

	U11	U22	U33	U12	U13	U23
Zn1	0.00708 (7)	0.00737 (7)	0.01160 (7)	−0.00038 (5)	0.00023 (5)	−0.00018 (5)
O1	0.0093 (4)	0.0106 (4)	0.0159 (4)	−0.0009 (3)	−0.0006 (3)	0.0007 (3)
O2	0.0161 (5)	0.0113 (5)	0.0573 (8)	−0.0044 (4)	−0.0058 (5)	0.0039 (5)
O3	0.0096 (4)	0.0164 (5)	0.0234 (5)	0.0031 (3)	0.0029 (4)	0.0053 (4)
O4	0.0101 (4)	0.0143 (4)	0.0279 (5)	0.0001 (3)	0.0030 (4)	−0.0020 (4)
O5	0.0089 (4)	0.0092 (4)	0.0148 (4)	−0.0007 (3)	0.0008 (3)	−0.0009 (3)
O6	0.0098 (4)	0.0143 (4)	0.0277 (5)	0.0015 (3)	−0.0013 (4)	0.0024 (4)
O7	0.0132 (4)	0.0094 (4)	0.0134 (4)	−0.0020 (3)	0.0035 (3)	0.0006 (3)
O8	0.0097 (4)	0.0159 (5)	0.0209 (5)	−0.0020 (3)	0.0001 (3)	0.0068 (4)
O9	0.0179 (5)	0.0108 (4)	0.0140 (4)	0.0025 (3)	0.0045 (3)	0.0017 (3)
N1	0.0086 (4)	0.0095 (5)	0.0100 (5)	0.0000 (3)	0.0015 (4)	−0.0007 (4)
N2	0.0090 (5)	0.0088 (4)	0.0094 (4)	−0.0001 (3)	0.0019 (4)	−0.0004 (3)
C1	0.0103 (5)	0.0105 (5)	0.0118 (5)	−0.0009 (4)	0.0010 (4)	0.0002 (4)
C2	0.0144 (6)	0.0083 (5)	0.0169 (6)	0.0002 (4)	0.0005 (5)	0.0005 (4)
C3	0.0124 (5)	0.0114 (6)	0.0161 (6)	0.0030 (4)	0.0014 (4)	0.0003 (4)
C4	0.0091 (5)	0.0126 (5)	0.0095 (5)	0.0014 (4)	0.0022 (4)	0.0006 (4)
C5	0.0096 (5)	0.0097 (5)	0.0103 (5)	0.0000 (4)	0.0014 (4)	−0.0003 (4)
C6	0.0115 (5)	0.0118 (5)	0.0182 (6)	−0.0019 (4)	0.0002 (5)	0.0011 (5)
C7	0.0083 (5)	0.0156 (6)	0.0110 (5)	0.0009 (4)	0.0024 (4)	0.0002 (4)
C8	0.0082 (5)	0.0110 (5)	0.0087 (5)	0.0000 (4)	0.0020 (4)	−0.0009 (4)
C9	0.0097 (5)	0.0103 (5)	0.0126 (5)	0.0016 (4)	0.0021 (4)	0.0002 (4)
C10	0.0127 (5)	0.0082 (5)	0.0117 (5)	−0.0003 (4)	0.0025 (4)	−0.0001 (4)
C11	0.0093 (5)	0.0098 (5)	0.0093 (5)	−0.0011 (4)	0.0027 (4)	−0.0007 (4)
C12	0.0085 (5)	0.0105 (5)	0.0108 (5)	−0.0003 (4)	0.0014 (4)	0.0003 (4)
C13	0.0093 (5)	0.0116 (5)	0.0103 (5)	−0.0007 (4)	0.0019 (4)	−0.0011 (4)
C14	0.0099 (5)	0.0102 (5)	0.0107 (5)	−0.0019 (4)	0.0034 (4)	−0.0014 (4)
N3	0.0084 (4)	0.0138 (5)	0.0125 (5)	0.0001 (4)	−0.0004 (4)	−0.0021 (4)
N4	0.0085 (4)	0.0145 (5)	0.0134 (5)	−0.0015 (4)	0.0008 (4)	−0.0031 (4)
C15	0.0136 (6)	0.0173 (6)	0.0134 (6)	−0.0029 (5)	0.0013 (5)	0.0012 (5)
C16	0.0150 (6)	0.0116 (6)	0.0175 (6)	−0.0013 (4)	0.0007 (5)	0.0000 (5)
C17	0.0116 (5)	0.0161 (6)	0.0130 (6)	−0.0028 (4)	0.0019 (4)	0.0001 (5)
C18	0.0123 (5)	0.0111 (5)	0.0161 (6)	−0.0005 (4)	0.0001 (4)	0.0000 (4)
O1W	0.0133 (4)	0.0167 (5)	0.0195 (5)	−0.0004 (4)	0.0002 (4)	0.0024 (4)
O2W	0.0142 (5)	0.0265 (5)	0.0203 (5)	0.0045 (4)	0.0007 (4)	−0.0099 (4)

Zn1—O1	2.0668 (9)	C8—C13	1.5208 (17)
Zn1—O5	2.0788 (9)	C9—C10	1.3874 (17)
Zn1—O9	2.0840 (9)	C9—H9C	0.9500
Zn1—N2	2.1222 (10)	C10—C11	1.3938 (17)
Zn1—N1	2.1445 (10)	C10—H10A	0.9500
Zn1—O7i	2.2209 (9)	C11—C12	1.3976 (16)
O1—C6	1.2675 (16)	C11—C14	1.5119 (16)
O2—C6	1.2372 (16)	C12—H12A	0.9500
O3—C7	1.2636 (15)	N3—C18	1.4888 (17)
O4—C7	1.2492 (16)	N3—C15	1.4941 (17)
O5—C13	1.2903 (15)	N3—H3B	0.9201
O6—C13	1.2239 (15)	N3—H3C	0.9200
O7—C14	1.2536 (15)	N4—C16	1.4852 (17)
O7—Zn1ii	2.2209 (9)	N4—C17	1.4877 (16)
O8—C14	1.2643 (15)	N4—H4A	0.9200
O9—H9A	0.8200	N4—H4B	0.9199
O9—H9B	0.8199	C15—C16	1.5156 (18)
N1—C5	1.3399 (15)	C15—H15A	0.9900
N1—C1	1.3461 (16)	C15—H15B	0.9900
N2—C12	1.3374 (15)	C16—H16A	0.9900
N2—C8	1.3472 (15)	C16—H16B	0.9900
C1—C2	1.3852 (17)	C17—C18	1.5167 (18)
C1—C6	1.5187 (17)	C17—H17A	0.9900
C2—C3	1.3898 (18)	C17—H17B	0.9900
C2—H2A	0.9500	C18—H18A	0.9900
C3—C4	1.3904 (17)	C18—H18B	0.9900
C3—H3A	0.9500	O1W—H1WA	0.8200
C4—C5	1.3946 (16)	O1W—H1WB	0.8200
C4—C7	1.5133 (17)	O2W—H2WA	0.8200
C5—H5A	0.9500	O2W—H2WB	0.8199
C8—C9	1.3859 (17)
O1—Zn1—O5	87.46 (3)	C9—C10—C11	119.48 (11)
O1—Zn1—O9	93.46 (4)	C9—C10—H10A	120.3
O5—Zn1—O9	91.78 (4)	C11—C10—H10A	120.3
O1—Zn1—N2	165.55 (4)	C10—C11—C12	117.73 (11)
O5—Zn1—N2	78.76 (4)	C10—C11—C14	121.67 (11)
O9—Zn1—N2	91.30 (4)	C12—C11—C14	120.52 (11)
O1—Zn1—N1	79.27 (4)	N2—C12—C11	123.05 (11)
O5—Zn1—N1	166.71 (4)	N2—C12—H12A	118.5
O9—Zn1—N1	88.45 (4)	C11—C12—H12A	118.5
N2—Zn1—N1	114.52 (4)	O6—C13—O5	126.08 (12)
O1—Zn1—O7i	90.82 (4)	O6—C13—C8	119.08 (11)
O5—Zn1—O7i	94.71 (3)	O5—C13—C8	114.84 (10)
O9—Zn1—O7i	172.38 (4)	O7—C14—O8	124.83 (11)
N2—Zn1—O7i	86.06 (4)	O7—C14—C11	117.47 (11)
N1—Zn1—O7i	86.15 (4)	O8—C14—C11	117.67 (11)
C6—O1—Zn1	116.57 (8)	C18—N3—C15	112.01 (10)
C13—O5—Zn1	117.11 (8)	C18—N3—H3B	109.2
C14—O7—Zn1ii	125.14 (8)	C15—N3—H3B	109.2
Zn1—O9—H9A	121.2	C18—N3—H3C	109.2
Zn1—O9—H9B	121.7	C15—N3—H3C	109.2
H9A—O9—H9B	111.0	H3B—N3—H3C	107.9
C5—N1—C1	118.15 (10)	C16—N4—C17	112.39 (10)
C5—N1—Zn1	130.51 (8)	C16—N4—H4A	109.1
C1—N1—Zn1	110.97 (8)	C17—N4—H4A	109.1
C12—N2—C8	118.47 (10)	C16—N4—H4B	109.1
C12—N2—Zn1	129.05 (8)	C17—N4—H4B	109.1
C8—N2—Zn1	112.47 (8)	H4A—N4—H4B	107.9
N1—C1—C2	122.48 (11)	N3—C15—C16	109.90 (10)
N1—C1—C6	116.52 (11)	N3—C15—H15A	109.7
C2—C1—C6	120.98 (11)	C16—C15—H15A	109.7
C1—C2—C3	119.02 (12)	N3—C15—H15B	109.7
C1—C2—H2A	120.5	C16—C15—H15B	109.7
C3—C2—H2A	120.5	H15A—C15—H15B	108.2
C2—C3—C4	119.13 (11)	N4—C16—C15	110.83 (11)
C2—C3—H3A	120.4	N4—C16—H16A	109.5
C4—C3—H3A	120.4	C15—C16—H16A	109.5
C3—C4—C5	118.03 (11)	N4—C16—H16B	109.5
C3—C4—C7	120.70 (11)	C15—C16—H16B	109.5
C5—C4—C7	121.19 (11)	H16A—C16—H16B	108.1
N1—C5—C4	123.18 (11)	N4—C17—C18	109.93 (10)
N1—C5—H5A	118.4	N4—C17—H17A	109.7
C4—C5—H5A	118.4	C18—C17—H17A	109.7
O2—C6—O1	126.75 (12)	N4—C17—H17B	109.7
O2—C6—C1	116.73 (12)	C18—C17—H17B	109.7
O1—C6—C1	116.51 (11)	H17A—C17—H17B	108.2
O4—C7—O3	124.76 (12)	N3—C18—C17	110.19 (10)
O4—C7—C4	119.32 (11)	N3—C18—H18A	109.6
O3—C7—C4	115.88 (11)	C17—C18—H18A	109.6
N2—C8—C9	122.37 (11)	N3—C18—H18B	109.6
N2—C8—C13	116.57 (10)	C17—C18—H18B	109.6
C9—C8—C13	121.04 (11)	H18A—C18—H18B	108.1
C8—C9—C10	118.85 (11)	H1WA—O1W—H1WB	105.7
C8—C9—H9C	120.6	H2WA—O2W—H2WB	107.0
C10—C9—H9C	120.6
O5—Zn1—O1—C6	−178.14 (10)	C7—C4—C5—N1	−175.31 (11)
O9—Zn1—O1—C6	90.24 (10)	Zn1—O1—C6—O2	178.27 (13)
N2—Zn1—O1—C6	−160.74 (14)	Zn1—O1—C6—C1	−0.95 (15)
N1—Zn1—O1—C6	2.47 (9)	N1—C1—C6—O2	178.30 (13)
O7i—Zn1—O1—C6	−83.46 (9)	C2—C1—C6—O2	−3.7 (2)
O1—Zn1—O5—C13	179.97 (9)	N1—C1—C6—O1	−2.41 (17)
O9—Zn1—O5—C13	−86.64 (9)	C2—C1—C6—O1	175.64 (12)
N2—Zn1—O5—C13	4.33 (9)	C3—C4—C7—O4	−176.67 (12)
N1—Zn1—O5—C13	−177.44 (14)	C5—C4—C7—O4	−0.21 (18)
O7i—Zn1—O5—C13	89.35 (9)	C3—C4—C7—O3	1.13 (17)
O1—Zn1—N1—C5	−176.42 (11)	C5—C4—C7—O3	177.58 (11)
O5—Zn1—N1—C5	−179.05 (13)	C12—N2—C8—C9	1.56 (18)
O9—Zn1—N1—C5	89.77 (11)	Zn1—N2—C8—C9	−177.67 (9)
N2—Zn1—N1—C5	−0.96 (12)	C12—N2—C8—C13	−176.63 (11)
O7i—Zn1—N1—C5	−84.85 (11)	Zn1—N2—C8—C13	4.14 (13)
O1—Zn1—N1—C1	−3.59 (8)	N2—C8—C9—C10	−2.33 (18)
O5—Zn1—N1—C1	−6.2 (2)	C13—C8—C9—C10	175.78 (11)
O9—Zn1—N1—C1	−97.41 (9)	C8—C9—C10—C11	1.14 (18)
N2—Zn1—N1—C1	171.87 (8)	C9—C10—C11—C12	0.67 (18)
O7i—Zn1—N1—C1	87.97 (8)	C9—C10—C11—C14	−176.08 (11)
O1—Zn1—N2—C12	158.72 (13)	C8—N2—C12—C11	0.41 (18)
O5—Zn1—N2—C12	176.45 (11)	Zn1—N2—C12—C11	179.49 (9)
O9—Zn1—N2—C12	−92.00 (11)	C10—C11—C12—N2	−1.51 (18)
N1—Zn1—N2—C12	−3.11 (12)	C14—C11—C12—N2	175.29 (11)
O7i—Zn1—N2—C12	80.84 (11)	Zn1—O5—C13—O6	176.62 (11)
O1—Zn1—N2—C8	−22.2 (2)	Zn1—O5—C13—C8	−3.37 (13)
O5—Zn1—N2—C8	−4.43 (8)	N2—C8—C13—O6	179.33 (12)
O9—Zn1—N2—C8	87.12 (8)	C9—C8—C13—O6	1.12 (18)
N1—Zn1—N2—C8	176.02 (8)	N2—C8—C13—O5	−0.67 (16)
O7i—Zn1—N2—C8	−100.03 (8)	C9—C8—C13—O5	−178.89 (11)
C5—N1—C1—C2	0.03 (18)	Zn1ii—O7—C14—O8	−82.76 (15)
Zn1—N1—C1—C2	−173.79 (10)	Zn1ii—O7—C14—C11	95.54 (12)
C5—N1—C1—C6	178.04 (11)	C10—C11—C14—O7	18.00 (17)
Zn1—N1—C1—C6	4.23 (13)	C12—C11—C14—O7	−158.66 (11)
N1—C1—C2—C3	0.9 (2)	C10—C11—C14—O8	−163.58 (12)
C6—C1—C2—C3	−177.05 (12)	C12—C11—C14—O8	19.76 (17)
C1—C2—C3—C4	−0.72 (19)	C18—N3—C15—C16	−56.65 (14)
C2—C3—C4—C5	−0.27 (18)	C17—N4—C16—C15	−56.30 (14)
C2—C3—C4—C7	176.29 (12)	N3—C15—C16—N4	55.00 (14)
C1—N1—C5—C4	−1.11 (18)	C16—N4—C17—C18	56.56 (14)
Zn1—N1—C5—C4	171.29 (9)	C15—N3—C18—C17	57.58 (13)
C3—C4—C5—N1	1.24 (18)	N4—C17—C18—N3	−56.24 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3iii	0.82	1.93	2.730 (1)	167
O1W—H1WB···O2	0.82	1.86	2.678 (2)	173
O2W—H2WA···O1W	0.82	1.87	2.682 (1)	174
N3—H3B···O8iv	0.92	1.82	2.741 (1)	177
N3—H3C···O1	0.92	2.46	2.912 (1)	111
N3—H3C···O5	0.92	1.94	2.818 (1)	158
O2W—H2WB···O5v	0.82	1.99	2.805 (1)	170
N4—H4A···O2Wvi	0.92	1.78	2.679 (2)	164
N4—H4B···O3vii	0.92	1.79	2.714 (1)	179
O9—H9A···O8viii	0.82	1.86	2.678 (1)	173
O9—H9B···O4viii	0.82	1.83	2.640 (1)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3i	0.82	1.93	2.730 (1)	167
O1W—H1WB⋯O2	0.82	1.86	2.678 (2)	173
O2W—H2WA⋯O1W	0.82	1.87	2.682 (1)	174
N3—H3B⋯O8ii	0.92	1.82	2.741 (1)	177
N3—H3C⋯O1	0.92	2.46	2.912 (1)	111
N3—H3C⋯O5	0.92	1.94	2.818 (1)	158
O2W—H2WB⋯O5iii	0.82	1.99	2.805 (1)	170
N4—H4A⋯O2Wiv	0.92	1.78	2.679 (2)	164
N4—H4B⋯O3v	0.92	1.79	2.714 (1)	179
O9—H9A⋯O8vi	0.82	1.86	2.678 (1)	173
O9—H9B⋯O4vi	0.82	1.83	2.640 (1)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .