Bis(2,6-diamino-pyridinium) bis-(pyridine-2,6-dicarboxyl-ato)zincate(II) monohydrate.

In the title hydrated mol-ecular salt, (C(5)H(8)N(3))(2)[Zn(C(7)H(3)NO(4))(2)]·H(2)O, the Zn(II) atom is coordinated by two O,N,O'-tridentate pyridine-2,6-dicarboxyl-ate dianions, generating a slightly distorted trans-ZnN(2)O(4) octa-hedral coordination geometry for the metal ion. In the crystal, a network of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds involving the cations, anions and water mol-ecules results in a three-dimensional network.

Related literature

For isostructural mol­ecular salts with Co and Ni, see: Moghimi et al. (2002 ▶). For related sturctures, see: Tabatabaee et al. (2009 ▶); Ranjbar et al. (2002 ▶); Moghimi et al. (2005 ▶).

Experimental

Crystal data

(C5H8N3)2[Zn(C7H3NO4)2]·H2O

M = 633.9

Monoclinic,

a = 8.2940 (3) Å

b = 13.2368 (4) Å

c = 23.8063 (7) Å

β = 104.995 (3)°

V = 2524.60 (14) Å3

Z = 4

Cu Kα radiation

μ = 1.99 mm−1

T = 120 K

0.26 × 0.19 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.142, T max = 1

66673 measured reflections

4502 independent reflections

4175 reflections with I > 3σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.077

S = 1.61

4502 reflections

415 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007) ▶; molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006 ▶.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018204/hb5879sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018204/hb5879Isup2.hkl

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

(C5H8N3)2[Zn(C7H3NO4)2]·H2O	F(000) = 1304
Mr = 633.9	Dx = 1.667 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 46751 reflections
a = 8.2940 (3) Å	θ = 3.3–67.0°
b = 13.2368 (4) Å	µ = 1.99 mm−1
c = 23.8063 (7) Å	T = 120 K
β = 104.995 (3)°	Block, colourless
V = 2524.60 (14) Å3	0.26 × 0.19 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	4502 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	4175 reflections with I > 3σ(I)
mirror	Rint = 0.031
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 3.8°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→15
Tmin = 0.142, Tmax = 1	l = −28→28
66673 measured reflections

Refinement on F2	60 constraints
R[F2 > 2σ(F2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.61	(Δ/σ)max = 0.002
4502 reflections	Δρmax = 0.20 e Å−3
415 parameters	Δρmin = −0.32 e Å−3
12 restraints

Experimental. CrysAlisPro, Oxford Diffraction (2009), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Zn1	0.73417 (2)	0.251250 (11)	0.490469 (7)	0.01551 (8)
O1	0.85536 (12)	0.30784 (7)	0.42606 (4)	0.0190 (3)
O2	0.90680 (12)	0.45264 (7)	0.38497 (4)	0.0203 (3)
O3	0.61404 (12)	0.27022 (7)	0.56153 (4)	0.0175 (3)
O4	0.56144 (12)	0.38883 (7)	0.62210 (4)	0.0185 (3)
O5	0.49822 (12)	0.22838 (7)	0.41879 (4)	0.0194 (3)
O6	0.38232 (13)	0.10376 (7)	0.35720 (4)	0.0266 (3)
O7	0.96377 (11)	0.19455 (7)	0.55438 (4)	0.0182 (3)
O8	1.05526 (12)	0.05147 (7)	0.60233 (4)	0.0213 (3)
N1	0.73813 (13)	0.40157 (8)	0.50291 (5)	0.0140 (3)
N2	0.71778 (13)	0.10107 (8)	0.48158 (4)	0.0141 (3)
N3	0.69954 (14)	0.60578 (8)	0.79837 (5)	0.0165 (3)
N4	0.67598 (16)	0.73531 (9)	0.86105 (5)	0.0197 (4)
N5	0.74582 (15)	0.47174 (9)	0.74142 (5)	0.0222 (4)
N6	0.84303 (14)	0.80163 (8)	0.72445 (5)	0.0165 (3)
N7	0.78444 (15)	0.93207 (9)	0.77987 (5)	0.0230 (4)
N8	0.87253 (16)	0.67785 (9)	0.66049 (5)	0.0229 (4)
C1	0.79561 (15)	0.46127 (9)	0.46716 (5)	0.0149 (4)
C2	0.79764 (16)	0.56544 (10)	0.47355 (5)	0.0174 (4)
C3	0.73738 (16)	0.60625 (10)	0.51793 (6)	0.0179 (4)
C4	0.67565 (15)	0.54303 (10)	0.55434 (5)	0.0165 (4)
C5	0.67867 (15)	0.44000 (9)	0.54554 (5)	0.0143 (4)
C6	0.85813 (15)	0.40324 (10)	0.42179 (5)	0.0163 (4)
C7	0.61279 (15)	0.35991 (9)	0.58001 (5)	0.0145 (4)
C8	0.59296 (16)	0.06081 (9)	0.44044 (5)	0.0151 (4)
C9	0.56638 (16)	−0.04242 (10)	0.43691 (5)	0.0170 (4)
C10	0.66832 (16)	−0.10379 (10)	0.47856 (6)	0.0180 (4)
C11	0.79717 (16)	−0.06116 (10)	0.52144 (6)	0.0169 (4)
C12	0.82002 (16)	0.04249 (10)	0.52096 (5)	0.0145 (4)
C13	0.48221 (16)	0.13793 (10)	0.40166 (5)	0.0173 (4)
C14	0.95791 (16)	0.10108 (10)	0.56312 (5)	0.0162 (4)
C15	0.62074 (16)	0.69111 (10)	0.80890 (5)	0.0169 (4)
C16	0.48878 (17)	0.72880 (11)	0.76506 (6)	0.0204 (4)
C17	0.44414 (17)	0.67788 (10)	0.71250 (6)	0.0222 (4)
C18	0.52517 (17)	0.59131 (10)	0.70276 (6)	0.0200 (4)
C19	0.65634 (16)	0.55427 (10)	0.74686 (5)	0.0170 (4)
C20	0.88001 (16)	0.85182 (10)	0.77596 (5)	0.0170 (4)
C21	1.01211 (17)	0.81712 (10)	0.82058 (6)	0.0197 (4)
C22	1.09920 (18)	0.73294 (11)	0.81063 (6)	0.0219 (4)
C23	1.05885 (17)	0.68247 (10)	0.75763 (6)	0.0214 (4)
C24	0.92679 (17)	0.71923 (11)	0.71358 (6)	0.0179 (4)
O9	0.13470 (16)	0.86262 (8)	0.64907 (5)	0.0345 (4)
H2	0.839584	0.608225	0.447989	0.0209*
H3	0.738256	0.678095	0.523516	0.0215*
H4	0.632137	0.570423	0.584768	0.0198*
H9	0.479364	−0.070943	0.406331	0.0204*
H10	0.65006	−0.175446	0.477824	0.0216*
H11	0.868503	−0.102603	0.550646	0.0203*
H16	0.430228	0.788661	0.771181	0.0245*
H17	0.354128	0.703644	0.681951	0.0266*
H18	0.491551	0.557035	0.666037	0.024*
H21	1.04204	0.850964	0.857491	0.0236*
H22	1.190356	0.708568	0.841236	0.0263*
H23	1.120325	0.623848	0.751528	0.0257*
H3n	0.7811 (18)	0.5828 (12)	0.8249 (6)	0.0199*
H4n	0.619 (2)	0.7832 (12)	0.8695 (7)	0.0237*
H4m	0.7661 (19)	0.7184 (14)	0.8843 (7)	0.0237*
H5n	0.711 (2)	0.4411 (13)	0.7078 (6)	0.0267*
H5m	0.798 (2)	0.4391 (13)	0.7727 (7)	0.0267*
H6n	0.7610 (18)	0.8265 (12)	0.6964 (6)	0.0198*
H7n	0.805 (2)	0.9661 (13)	0.8120 (6)	0.0276*
H7m	0.701 (2)	0.9456 (14)	0.7516 (7)	0.0276*
H8n	0.933 (2)	0.6358 (12)	0.6492 (7)	0.0275*
H8m	0.787 (2)	0.7089 (14)	0.6359 (7)	0.0275*
H9o	0.130 (3)	0.8128 (14)	0.6273 (9)	0.0517*
H9p	0.100 (3)	0.9126 (14)	0.6256 (9)	0.0517*

	U11	U22	U33	U12	U13	U23
Zn1	0.02022 (13)	0.00980 (13)	0.01659 (13)	−0.00032 (6)	0.00492 (9)	−0.00079 (5)
O1	0.0250 (5)	0.0150 (4)	0.0187 (4)	−0.0002 (4)	0.0087 (4)	−0.0008 (3)
O2	0.0226 (5)	0.0217 (5)	0.0178 (4)	0.0023 (4)	0.0075 (4)	0.0046 (4)
O3	0.0208 (5)	0.0134 (4)	0.0190 (5)	−0.0020 (4)	0.0066 (4)	−0.0013 (3)
O4	0.0212 (5)	0.0190 (5)	0.0163 (4)	−0.0019 (4)	0.0066 (4)	−0.0023 (3)
O5	0.0217 (5)	0.0151 (4)	0.0191 (5)	0.0023 (4)	0.0013 (4)	0.0006 (4)
O6	0.0279 (5)	0.0220 (5)	0.0223 (5)	0.0004 (4)	−0.0070 (4)	−0.0007 (4)
O7	0.0189 (5)	0.0142 (4)	0.0196 (4)	−0.0009 (3)	0.0018 (3)	−0.0017 (3)
O8	0.0203 (5)	0.0185 (5)	0.0204 (5)	0.0008 (4)	−0.0033 (4)	0.0003 (4)
N1	0.0143 (5)	0.0125 (6)	0.0141 (5)	−0.0004 (4)	0.0017 (4)	0.0007 (4)
N2	0.0156 (5)	0.0123 (5)	0.0146 (5)	0.0007 (4)	0.0044 (4)	0.0004 (4)
N3	0.0164 (6)	0.0170 (5)	0.0153 (5)	0.0016 (4)	0.0025 (4)	0.0005 (4)
N4	0.0209 (6)	0.0189 (5)	0.0190 (6)	0.0047 (5)	0.0044 (5)	−0.0023 (4)
N5	0.0288 (7)	0.0187 (6)	0.0184 (6)	0.0038 (5)	0.0045 (5)	−0.0021 (4)
N6	0.0173 (6)	0.0170 (5)	0.0142 (5)	−0.0004 (4)	0.0024 (4)	−0.0006 (4)
N7	0.0262 (7)	0.0201 (6)	0.0207 (6)	0.0027 (5)	0.0024 (5)	−0.0064 (5)
N8	0.0235 (7)	0.0246 (6)	0.0206 (6)	0.0001 (5)	0.0055 (5)	−0.0076 (5)
C1	0.0131 (6)	0.0156 (6)	0.0146 (6)	0.0002 (5)	0.0012 (5)	0.0022 (5)
C2	0.0165 (6)	0.0160 (6)	0.0179 (6)	−0.0003 (5)	0.0009 (5)	0.0037 (5)
C3	0.0180 (6)	0.0114 (6)	0.0210 (6)	0.0005 (5)	−0.0009 (5)	−0.0009 (5)
C4	0.0149 (6)	0.0166 (6)	0.0161 (6)	0.0006 (5)	0.0007 (5)	−0.0021 (5)
C5	0.0119 (6)	0.0162 (6)	0.0131 (6)	−0.0003 (5)	0.0000 (4)	−0.0015 (5)
C6	0.0146 (6)	0.0182 (6)	0.0147 (6)	0.0009 (5)	0.0015 (5)	0.0012 (5)
C7	0.0129 (6)	0.0155 (6)	0.0136 (6)	−0.0012 (5)	0.0004 (5)	−0.0014 (5)
C8	0.0151 (6)	0.0167 (6)	0.0135 (5)	0.0008 (5)	0.0037 (5)	−0.0014 (4)
C9	0.0167 (6)	0.0169 (6)	0.0169 (6)	−0.0023 (5)	0.0035 (5)	−0.0033 (5)
C10	0.0204 (7)	0.0118 (6)	0.0226 (6)	−0.0015 (5)	0.0071 (5)	−0.0006 (5)
C11	0.0171 (7)	0.0161 (6)	0.0174 (6)	0.0016 (5)	0.0041 (5)	0.0015 (5)
C12	0.0142 (6)	0.0156 (6)	0.0137 (6)	0.0014 (5)	0.0036 (5)	−0.0001 (5)
C13	0.0175 (7)	0.0174 (6)	0.0168 (6)	0.0005 (5)	0.0040 (5)	0.0006 (5)
C14	0.0164 (6)	0.0164 (6)	0.0162 (6)	0.0000 (5)	0.0050 (5)	−0.0012 (5)
C15	0.0168 (7)	0.0169 (6)	0.0189 (6)	−0.0015 (5)	0.0082 (5)	0.0010 (5)
C16	0.0182 (7)	0.0201 (6)	0.0231 (7)	0.0035 (6)	0.0058 (5)	0.0006 (5)
C17	0.0174 (7)	0.0270 (8)	0.0206 (6)	0.0006 (5)	0.0021 (5)	0.0029 (5)
C18	0.0202 (7)	0.0243 (7)	0.0155 (6)	−0.0022 (5)	0.0045 (5)	−0.0007 (5)
C19	0.0183 (6)	0.0171 (6)	0.0172 (6)	−0.0034 (5)	0.0073 (5)	−0.0010 (5)
C20	0.0184 (7)	0.0165 (6)	0.0174 (6)	−0.0035 (5)	0.0071 (5)	−0.0014 (5)
C21	0.0199 (7)	0.0232 (7)	0.0150 (6)	−0.0038 (5)	0.0028 (5)	−0.0018 (5)
C22	0.0172 (7)	0.0251 (7)	0.0219 (7)	−0.0007 (6)	0.0020 (5)	0.0037 (5)
C23	0.0185 (7)	0.0214 (7)	0.0245 (7)	0.0020 (5)	0.0061 (5)	−0.0004 (5)
C24	0.0173 (7)	0.0188 (6)	0.0194 (6)	−0.0038 (5)	0.0082 (5)	−0.0016 (5)
O9	0.0590 (8)	0.0185 (5)	0.0210 (5)	0.0045 (5)	0.0017 (5)	−0.0002 (4)

Zn1—O1	2.1725 (10)	N8—H8m	0.895 (15)
Zn1—O3	2.1886 (11)	C1—C2	1.3868 (18)
Zn1—O5	2.2595 (9)	C1—C6	1.5216 (19)
Zn1—O7	2.2372 (8)	C2—C3	1.390 (2)
Zn1—N1	2.0107 (11)	C2—H2	0.96
Zn1—N2	2.0001 (11)	C3—C4	1.394 (2)
O1—C6	1.2676 (16)	C3—H3	0.96
O2—C6	1.2418 (17)	C4—C5	1.3810 (18)
O3—C7	1.2671 (16)	C4—H4	0.96
O4—C7	1.2460 (16)	C5—C7	1.5256 (18)
O5—C13	1.2607 (16)	C8—C9	1.3832 (18)
O6—C13	1.2481 (15)	C8—C13	1.5163 (17)
O7—C14	1.2577 (15)	C9—C10	1.3871 (17)
O8—C14	1.2508 (14)	C9—H9	0.96
N1—C1	1.3364 (18)	C10—C11	1.3920 (17)
N1—C5	1.3383 (18)	C10—H10	0.96
N2—C8	1.3380 (15)	C11—C12	1.3855 (18)
N2—C12	1.3370 (15)	C11—H11	0.96
N3—C15	1.3604 (18)	C12—C14	1.5240 (16)
N3—C19	1.3672 (16)	C15—C16	1.3945 (17)
N3—H3n	0.854 (13)	C16—C17	1.3846 (19)
N4—C15	1.3413 (17)	C16—H16	0.96
N4—H4n	0.845 (17)	C17—C18	1.378 (2)
N4—H4m	0.838 (14)	C17—H17	0.96
N5—C19	1.3457 (18)	C18—C19	1.3912 (17)
N5—H5n	0.878 (15)	C18—H18	0.96
N5—H5m	0.872 (15)	C20—C21	1.3920 (17)
N6—C20	1.3581 (16)	C21—C22	1.381 (2)
N6—C24	1.3536 (18)	C21—H21	0.96
N6—H6n	0.884 (14)	C22—C23	1.390 (2)
N7—C20	1.3429 (18)	C22—H22	0.96
N7—H7n	0.866 (15)	C23—C24	1.3934 (17)
N7—H7m	0.850 (14)	C23—H23	0.96
N8—C24	1.3437 (17)	O9—H9o	0.83 (2)
N8—H8n	0.840 (18)	O9—H9p	0.866 (19)
O1—Zn1—O3	153.16 (4)	O1—C6—O2	126.67 (13)
O1—Zn1—O5	88.95 (4)	O1—C6—C1	115.43 (12)
O1—Zn1—O7	97.34 (4)	O2—C6—C1	117.90 (11)
O1—Zn1—N1	76.69 (4)	O3—C7—O4	127.03 (12)
O1—Zn1—N2	107.41 (4)	O3—C7—C5	115.34 (11)
O3—Zn1—O5	96.92 (4)	O4—C7—C5	117.62 (11)
O3—Zn1—O7	89.46 (3)	N2—C8—C9	121.25 (11)
O3—Zn1—N1	76.46 (4)	N2—C8—C13	114.18 (11)
O3—Zn1—N2	99.43 (4)	C9—C8—C13	124.49 (10)
O5—Zn1—O7	152.52 (3)	C8—C9—C10	118.50 (11)
O5—Zn1—N1	102.81 (4)	C8—C9—H9	120.7524
O5—Zn1—N2	76.41 (4)	C10—C9—H9	120.7525
O7—Zn1—N1	104.67 (3)	C9—C10—C11	119.81 (12)
O7—Zn1—N2	76.18 (3)	C9—C10—H10	120.0969
N1—Zn1—N2	175.74 (5)	C11—C10—H10	120.0967
Zn1—O1—C6	114.92 (9)	C10—C11—C12	118.43 (11)
Zn1—O3—C7	114.97 (9)	C10—C11—H11	120.7863
Zn1—O5—C13	111.69 (7)	C12—C11—H11	120.7859
Zn1—O7—C14	112.33 (7)	N2—C12—C11	121.11 (10)
Zn1—N1—C1	119.10 (9)	N2—C12—C14	113.48 (11)
Zn1—N1—C5	119.51 (9)	C11—C12—C14	125.41 (10)
C1—N1—C5	121.36 (11)	O5—C13—O6	127.57 (11)
Zn1—N2—C8	119.46 (8)	O5—C13—C8	116.49 (10)
Zn1—N2—C12	119.26 (8)	O6—C13—C8	115.91 (11)
C8—N2—C12	120.83 (11)	O7—C14—O8	126.50 (11)
C15—N3—C19	123.53 (10)	O7—C14—C12	116.50 (10)
C15—N3—H3n	119.1 (11)	O8—C14—C12	116.99 (11)
C19—N3—H3n	117.4 (11)	N3—C15—N4	117.86 (11)
C15—N4—H4n	118.0 (10)	N3—C15—C16	118.72 (12)
C15—N4—H4m	121.9 (12)	N4—C15—C16	123.41 (13)
H4n—N4—H4m	120.0 (16)	C15—C16—C17	118.47 (13)
C19—N5—H5n	113.8 (11)	C15—C16—H16	120.7643
C19—N5—H5m	118.9 (12)	C17—C16—H16	120.7632
H5n—N5—H5m	121.5 (15)	C16—C17—C18	121.93 (12)
C20—N6—C24	124.03 (10)	C16—C17—H17	119.0364
C20—N6—H6n	116.7 (10)	C18—C17—H17	119.0372
C24—N6—H6n	119.3 (10)	C17—C18—C19	119.09 (12)
C20—N7—H7n	119.2 (11)	C17—C18—H18	120.4552
C20—N7—H7m	119.1 (12)	C19—C18—H18	120.4557
H7n—N7—H7m	121.5 (16)	N3—C19—N5	117.91 (10)
C24—N8—H8n	119.2 (10)	N3—C19—C18	118.26 (12)
C24—N8—H8m	116.3 (11)	N5—C19—C18	123.81 (12)
H8n—N8—H8m	122.5 (16)	N6—C20—N7	116.75 (11)
N1—C1—C2	120.95 (12)	N6—C20—C21	118.49 (12)
N1—C1—C6	113.37 (11)	N7—C20—C21	124.76 (12)
C2—C1—C6	125.67 (12)	C20—C21—C22	118.59 (12)
C1—C2—C3	118.25 (13)	C20—C21—H21	120.7048
C1—C2—H2	120.8742	C22—C21—H21	120.7055
C3—C2—H2	120.873	C21—C22—C23	121.98 (12)
C2—C3—C4	120.10 (12)	C21—C22—H22	119.0091
C2—C3—H3	119.9475	C23—C22—H22	119.0085
C4—C3—H3	119.949	C22—C23—C24	118.24 (13)
C3—C4—C5	118.32 (13)	C22—C23—H23	120.8827
C3—C4—H4	120.8394	C24—C23—H23	120.881
C5—C4—H4	120.8387	N6—C24—N8	116.41 (11)
N1—C5—C4	121.00 (12)	N6—C24—C23	118.68 (12)
N1—C5—C7	113.41 (11)	N8—C24—C23	124.90 (13)
C4—C5—C7	125.55 (12)	H9o—O9—H9p	104.4 (19)
O3—Zn1—O1—C6	−6.33 (14)	Zn1—N1—C1—C2	178.80 (9)
O5—Zn1—O1—C6	97.02 (9)	Zn1—N1—C1—C6	−2.24 (14)
O7—Zn1—O1—C6	−109.82 (9)	C5—N1—C1—C2	0.87 (19)
N1—Zn1—O1—C6	−6.41 (9)	C5—N1—C1—C6	179.83 (11)
N2—Zn1—O1—C6	172.42 (9)	Zn1—N1—C5—C4	−178.36 (9)
O1—Zn1—O3—C7	−4.88 (14)	Zn1—N1—C5—C7	−0.20 (14)
O5—Zn1—O3—C7	−106.37 (9)	C1—N1—C5—C4	−0.43 (19)
O7—Zn1—O3—C7	100.44 (9)	C1—N1—C5—C7	177.72 (11)
N1—Zn1—O3—C7	−4.80 (9)	Zn1—N2—C8—C9	−172.85 (10)
N2—Zn1—O3—C7	176.33 (9)	Zn1—N2—C8—C13	4.06 (14)
O1—Zn1—O5—C13	98.37 (9)	C12—N2—C8—C9	−0.59 (19)
O3—Zn1—O5—C13	−107.90 (9)	C12—N2—C8—C13	176.32 (11)
O7—Zn1—O5—C13	−5.62 (13)	Zn1—N2—C12—C11	170.43 (10)
N1—Zn1—O5—C13	174.47 (9)	Zn1—N2—C12—C14	−9.58 (14)
N2—Zn1—O5—C13	−9.83 (9)	C8—N2—C12—C11	−1.85 (19)
O1—Zn1—O7—C14	−119.53 (9)	C8—N2—C12—C14	178.14 (11)
O3—Zn1—O7—C14	86.52 (9)	N1—C1—C2—C3	−0.37 (19)
O5—Zn1—O7—C14	−17.54 (13)	C6—C1—C2—C3	−179.19 (12)
N1—Zn1—O7—C14	162.37 (9)	N1—C1—C6—O1	−3.56 (16)
N2—Zn1—O7—C14	−13.33 (8)	N1—C1—C6—O2	176.76 (11)
O1—Zn1—N1—C1	4.42 (9)	C2—C1—C6—O1	175.34 (12)
O1—Zn1—N1—C5	−177.61 (10)	C2—C1—C6—O2	−4.34 (19)
O3—Zn1—N1—C1	−175.54 (10)	C1—C2—C3—C4	−0.54 (19)
O3—Zn1—N1—C5	2.43 (9)	C2—C3—C4—C5	0.96 (19)
O5—Zn1—N1—C1	−81.39 (10)	C3—C4—C5—N1	−0.48 (19)
O5—Zn1—N1—C5	96.58 (10)	C3—C4—C5—C7	−178.40 (12)
O7—Zn1—N1—C1	98.66 (10)	N1—C5—C7—O3	−4.10 (16)
O7—Zn1—N1—C5	−83.38 (10)	N1—C5—C7—O4	177.08 (11)
O1—Zn1—N2—C8	−82.06 (10)	C4—C5—C7—O3	173.95 (12)
O1—Zn1—N2—C12	105.56 (10)	C4—C5—C7—O4	−4.86 (19)
O3—Zn1—N2—C8	97.37 (10)	N2—C8—C9—C10	2.52 (19)
O3—Zn1—N2—C12	−75.02 (10)	C13—C8—C9—C10	−174.06 (12)
O5—Zn1—N2—C8	2.46 (9)	N2—C8—C13—O5	−13.36 (17)
O5—Zn1—N2—C12	−169.93 (10)	N2—C8—C13—O6	168.57 (12)
O7—Zn1—N2—C8	−175.54 (10)	C9—C8—C13—O5	163.43 (13)
O7—Zn1—N2—C12	12.07 (9)	C9—C8—C13—O6	−14.64 (19)
Zn1—O1—C6—O2	−173.25 (11)	C8—C9—C10—C11	−2.1 (2)
Zn1—O1—C6—C1	7.10 (14)	C9—C10—C11—C12	−0.2 (2)
Zn1—O3—C7—O4	−175.28 (11)	C10—C11—C12—N2	2.2 (2)
Zn1—O3—C7—C5	6.04 (14)	C10—C11—C12—C14	−177.76 (12)
Zn1—O5—C13—O6	−167.46 (12)	N2—C12—C14—O7	−3.18 (17)
Zn1—O5—C13—C8	14.74 (14)	N2—C12—C14—O8	177.85 (11)
Zn1—O7—C14—O8	−168.70 (11)	C11—C12—C14—O7	176.81 (13)
Zn1—O7—C14—C12	12.44 (14)	C11—C12—C14—O8	−2.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3i	0.96	2.49	3.1769 (16)	129
C18—H18···O4	0.96	2.59	3.3556 (16)	137
C22—H22···O3ii	0.96	2.59	3.3789 (17)	139
N3—H3n···O8ii	0.854 (13)	1.948 (13)	2.7845 (13)	166.0 (16)
N4—H4n···O4iii	0.845 (17)	2.096 (17)	2.9287 (16)	168.4 (14)
N4—H4m···O7ii	0.838 (14)	2.357 (14)	3.1874 (14)	171.0 (17)
N5—H5n···O4	0.878 (15)	2.206 (14)	3.0600 (14)	164.2 (15)
N5—H5m···O9iv	0.872 (15)	2.066 (15)	2.9203 (15)	166.3 (17)
N6—H6n···O6v	0.884 (14)	1.763 (14)	2.6381 (13)	169.9 (15)
N7—H7n···O2vi	0.866 (15)	2.032 (15)	2.8818 (15)	166.8 (17)
N8—H8n···O2vii	0.840 (18)	2.085 (18)	2.9206 (17)	172.4 (17)
O9—H9o···O1v	0.83 (2)	2.06 (2)	2.8936 (14)	174 (2)
O9—H9p···O8viii	0.866 (19)	1.928 (19)	2.7462 (14)	157.1 (18)

Table 1

Selected bond lengths (Å)

Zn1—O1	2.1725 (10)
Zn1—O3	2.1886 (11)
Zn1—O5	2.2595 (9)
Zn1—O7	2.2372 (8)
Zn1—N1	2.0107 (11)
Zn1—N2	2.0001 (11)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3i	0.96	2.49	3.1769 (16)	129
C18—H18⋯O4	0.96	2.59	3.3556 (16)	137
C22—H22⋯O3ii	0.96	2.59	3.3789 (17)	139
N3—H3n⋯O8ii	0.854 (13)	1.948 (13)	2.7845 (13)	166.0 (16)
N4—H4n⋯O4iii	0.845 (17)	2.096 (17)	2.9287 (16)	168.4 (14)
N4—H4m⋯O7ii	0.838 (14)	2.357 (14)	3.1874 (14)	171.0 (17)
N5—H5n⋯O4	0.878 (15)	2.206 (14)	3.0600 (14)	164.2 (15)
N5—H5m⋯O9iv	0.872 (15)	2.066 (15)	2.9203 (15)	166.3 (17)
N6—H6n⋯O6v	0.884 (14)	1.763 (14)	2.6381 (13)	169.9 (15)
N7—H7n⋯O2vi	0.866 (15)	2.032 (15)	2.8818 (15)	166.8 (17)
N8—H8n⋯O2vii	0.840 (18)	2.085 (18)	2.9206 (17)	172.4 (17)
O9—H9o⋯O1v	0.83 (2)	2.06 (2)	2.8936 (14)	174 (2)
O9—H9p⋯O8viii	0.866 (19)	1.928 (19)	2.7462 (14)	157.1 (18)

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