Diaqua-bis[4-(dimethyl-amino)benzoato](isonicotinamide)zinc(II).

The mol-ecule of the title Zn(II) complex, [Zn(C(9)H(10)NO(2))(2)(C(6)H(6)N(2)O)(H(2)O)(2)], contains two 4-(dimethyl-amino)benzoate (DMAB) ligands, one isonicotinamide (INA) ligand and two water mol-ecules; one of the DMAB ions acts as a bidentate ligand while the other and INA are monodentate ligands. The four O atoms in the equatorial plane around the Zn atom form a distorted square-planar arrangement, while the distorted octa-hedral coordination is completed by the N atom of the INA ligand and the O atom of the water mol-ecule in the axial positions. Intra-molecular C-H⋯O hydrogen bonding results in the formation of a six-membered ring adopting an envelope conformation. The dihedral angle between the carboxyl groups and the adjacent benzene rings are 4.87 (16) and 2.2 (2)°, while the two benzene rings are oriented at a dihedral angle of 65.13 (8)°. The dihedral angle between the benzene and pyridine rings are 11.47 (7) and 74.83 (8)°, respectively. In the crystal structure, inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular structure. π-π contacts between the pyridine and benzene rings and between the benzene rings [centroid-centroid distances = 3.695 (1) and 3.841 (1) Å, respectively] further stabilize the structure. Weak inter-molecular C-H⋯π inter-actions are also present.

Related literature

For general backgroud, see: Antolini et al. (1982 ▶); Chen & Chen (2002 ▶); Amiraslanov et al. (1979 ▶); Bigoli et al. (1972 ▶); Hauptmann et al. (2000 ▶); Shnulin et al. (1981 ▶); Antsyshkina et al. (1980 ▶); Adiwidjaja et al. (1978 ▶); Catterick et al. (1974 ▶); Krishnamachari (1974 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶, 2008 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶).

Experimental

Crystal data

[Zn(n class="CellLine">C9H10NO2)2(C6H6N2O)(H2O)2]

M = 551.91

Triclinic,

a = 6.8616 (2) Å

b = 8.0947 (3) Å

c = 22.4953 (4) Å

α = 90.683 (2)°

β = 92.838 (2)°

γ = 93.313 (3)°

V = 1245.69 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 100 K

0.57 × 0.27 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.720, T max = 0.810

21315 measured reflections

6053 independent reflections

5647 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.078

S = 1.29

6053 reflections

353 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.99 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017620/xu2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017620/xu2522Isup2.hkl

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

[Zn(C9H10NO2)2(C6H6N2O)(H2O)2]	Z = 2
Mr = 551.91	F(000) = 576
Triclinic, P1	Dx = 1.471 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8616 (2) Å	Cell parameters from 9908 reflections
b = 8.0947 (3) Å	θ = 2.7–28.4°
c = 22.4953 (4) Å	µ = 1.04 mm−1
α = 90.683 (2)°	T = 100 K
β = 92.838 (2)°	Block, colorless
γ = 93.313 (3)°	0.57 × 0.27 × 0.20 mm
V = 1245.69 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	6053 independent reflections
Radiation source: fine-focus sealed tube	5647 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.720, Tmax = 0.810	k = −10→10
21315 measured reflections	l = −30→30

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ2(Fo2) + 1.9543P] where P = (Fo2 + 2Fc2)/3
6053 reflections	(Δ/σ)max = 0.001
353 parameters	Δρmax = 0.43 e Å−3
6 restraints	Δρmin = −0.99 e Å−3

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	0.43308 (4)	0.52665 (3)	0.277312 (12)	0.00968 (7)
O1	0.6072 (2)	0.6802 (2)	0.33222 (7)	0.0139 (3)
O2	0.8588 (2)	0.5241 (2)	0.35273 (8)	0.0151 (3)
O3	0.3267 (2)	0.4011 (2)	0.19727 (7)	0.0136 (3)
O4	0.6263 (2)	0.5140 (2)	0.19916 (7)	0.0140 (3)
O5	−0.3021 (2)	1.0876 (2)	0.23256 (8)	0.0152 (3)
O6	0.5716 (2)	0.3151 (2)	0.31154 (8)	0.0137 (3)
H61	0.683 (3)	0.366 (4)	0.3259 (14)	0.034 (9)*
H62	0.605 (5)	0.250 (4)	0.2826 (13)	0.043 (11)*
O7	0.2121 (2)	0.4297 (2)	0.32786 (8)	0.0156 (4)
H71	0.241 (5)	0.362 (4)	0.3573 (12)	0.041 (10)*
H72	0.102 (4)	0.471 (4)	0.3366 (15)	0.040 (10)*
N1	0.2604 (3)	0.7288 (2)	0.25405 (8)	0.0111 (4)
N2	−0.0589 (3)	1.2657 (3)	0.20535 (10)	0.0150 (4)
H21	−0.144 (5)	1.345 (4)	0.2033 (14)	0.028 (9)*
H22	0.065 (5)	1.293 (4)	0.1978 (14)	0.026 (8)*
N3	1.2354 (3)	1.2427 (2)	0.43495 (9)	0.0134 (4)
N4	0.5670 (4)	0.1902 (3)	−0.06335 (10)	0.0295 (6)
C1	0.7806 (3)	0.6619 (3)	0.35163 (10)	0.0118 (4)
C2	0.8980 (3)	0.8119 (3)	0.37526 (10)	0.0116 (4)
C3	1.0944 (3)	0.8040 (3)	0.39285 (10)	0.0133 (4)
H3	1.1525	0.7032	0.3907	0.016*
C4	1.2056 (3)	0.9437 (3)	0.41358 (10)	0.0137 (4)
H4	1.3366	0.9350	0.4251	0.016*
C5	1.1230 (3)	1.0971 (3)	0.41741 (10)	0.0116 (4)
C6	0.9246 (3)	1.1047 (3)	0.39978 (11)	0.0148 (5)
H6	0.8656	1.2049	0.4023	0.018*
C7	0.8157 (3)	0.9653 (3)	0.37883 (10)	0.0138 (5)
H7	0.6850	0.9738	0.3669	0.017*
C8	0.4856 (3)	0.4329 (3)	0.17119 (10)	0.0118 (4)
C9	0.5045 (4)	0.3732 (3)	0.10964 (10)	0.0138 (5)
C10	0.3518 (4)	0.2825 (3)	0.07888 (11)	0.0186 (5)
H10	0.2349	0.2609	0.0974	0.022*
C11	0.3696 (4)	0.2240 (3)	0.02182 (12)	0.0223 (5)
H11	0.2643	0.1656	0.0022	0.027*
C12	0.5457 (4)	0.2517 (3)	−0.00729 (11)	0.0223 (6)
C13	0.6994 (4)	0.3448 (3)	0.02368 (12)	0.0227 (6)
H13	0.8169	0.3664	0.0056	0.027*
C14	0.6774 (4)	0.4042 (3)	0.08049 (11)	0.0181 (5)
H14	0.7802	0.4665	0.0999	0.022*
C15	0.3272 (3)	0.8873 (3)	0.25996 (10)	0.0134 (5)
H15	0.4576	0.9101	0.2721	0.016*
C16	0.2101 (3)	1.0188 (3)	0.24869 (11)	0.0138 (5)
H16	0.2620	1.1274	0.2524	0.017*
C17	0.0147 (3)	0.9856 (3)	0.23173 (10)	0.0103 (4)
C18	−0.0561 (3)	0.8214 (3)	0.22551 (10)	0.0117 (4)
H18	−0.1868	0.7952	0.2145	0.014*
C19	0.0719 (3)	0.6980 (3)	0.23603 (10)	0.0120 (4)
H19	0.0254	0.5884	0.2304	0.014*
C20	1.1361 (4)	1.3649 (3)	0.46894 (11)	0.0172 (5)
H20A	1.2236	1.4601	0.4773	0.026*
H20B	1.0964	1.3173	0.5056	0.026*
H20C	1.0230	1.3975	0.4462	0.026*
C21	1.4337 (4)	1.2219 (3)	0.45885 (13)	0.0240 (6)
H21A	1.4981	1.3285	0.4675	0.036*
H21B	1.5046	1.1645	0.4301	0.036*
H21C	1.4290	1.1589	0.4947	0.036*
C22	0.7510 (5)	0.2163 (4)	−0.09166 (13)	0.0376 (8)
H22A	0.7477	0.1513	−0.1277	0.056*
H22B	0.8556	0.1835	−0.0652	0.056*
H22C	0.7719	0.3313	−0.1008	0.056*
C23	0.4016 (5)	0.1097 (4)	−0.09693 (13)	0.0358 (8)
H23A	0.4403	0.0798	−0.1359	0.054*
H23B	0.2978	0.1841	−0.1005	0.054*
H23C	0.3572	0.0119	−0.0767	0.054*
C24	−0.1275 (3)	1.1191 (3)	0.22302 (10)	0.0117 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.00962 (12)	0.00784 (13)	0.01170 (12)	0.00169 (9)	0.00048 (9)	−0.00011 (9)
O1	0.0114 (8)	0.0130 (8)	0.0170 (8)	0.0028 (6)	−0.0028 (6)	−0.0015 (6)
O2	0.0125 (8)	0.0096 (8)	0.0232 (9)	0.0023 (6)	−0.0006 (7)	−0.0010 (7)
O3	0.0134 (8)	0.0131 (8)	0.0145 (8)	−0.0001 (6)	0.0033 (6)	−0.0011 (6)
O4	0.0138 (8)	0.0123 (8)	0.0156 (8)	−0.0018 (6)	−0.0003 (6)	−0.0008 (6)
O5	0.0109 (8)	0.0115 (8)	0.0232 (9)	0.0010 (6)	0.0018 (7)	−0.0018 (7)
O6	0.0108 (8)	0.0128 (9)	0.0177 (8)	0.0020 (6)	0.0005 (6)	0.0000 (7)
O7	0.0133 (8)	0.0166 (9)	0.0180 (8)	0.0055 (7)	0.0050 (7)	0.0059 (7)
N1	0.0113 (9)	0.0118 (10)	0.0102 (9)	−0.0001 (7)	0.0011 (7)	0.0004 (7)
N2	0.0107 (10)	0.0095 (10)	0.0249 (11)	0.0017 (8)	−0.0012 (8)	0.0026 (8)
N3	0.0125 (9)	0.0118 (10)	0.0155 (9)	0.0011 (7)	−0.0012 (7)	−0.0021 (8)
N4	0.0458 (16)	0.0308 (14)	0.0131 (11)	0.0092 (12)	0.0045 (10)	−0.0039 (9)
C1	0.0141 (11)	0.0119 (11)	0.0096 (10)	0.0010 (8)	0.0016 (8)	−0.0002 (8)
C2	0.0127 (11)	0.0122 (11)	0.0100 (10)	0.0003 (8)	0.0011 (8)	−0.0001 (8)
C3	0.0140 (11)	0.0104 (11)	0.0157 (11)	0.0027 (8)	0.0004 (9)	0.0006 (9)
C4	0.0115 (11)	0.0148 (12)	0.0148 (11)	0.0022 (9)	−0.0014 (8)	0.0011 (9)
C5	0.0140 (11)	0.0111 (11)	0.0097 (10)	0.0005 (8)	0.0004 (8)	0.0007 (8)
C6	0.0143 (11)	0.0114 (11)	0.0189 (11)	0.0044 (9)	−0.0005 (9)	−0.0010 (9)
C7	0.0114 (11)	0.0143 (12)	0.0156 (11)	0.0024 (9)	−0.0009 (8)	−0.0008 (9)
C8	0.0120 (11)	0.0088 (11)	0.0151 (11)	0.0027 (8)	0.0007 (8)	0.0017 (8)
C9	0.0170 (11)	0.0120 (11)	0.0126 (11)	0.0027 (9)	0.0009 (9)	0.0007 (8)
C10	0.0202 (13)	0.0200 (13)	0.0154 (12)	0.0008 (10)	0.0003 (9)	−0.0016 (10)
C11	0.0285 (14)	0.0203 (14)	0.0176 (12)	0.0024 (11)	−0.0044 (10)	−0.0039 (10)
C12	0.0370 (16)	0.0181 (13)	0.0128 (11)	0.0090 (11)	0.0020 (10)	0.0007 (10)
C13	0.0274 (14)	0.0234 (14)	0.0186 (12)	0.0053 (11)	0.0093 (10)	0.0029 (10)
C14	0.0213 (13)	0.0170 (13)	0.0162 (11)	0.0013 (10)	0.0035 (9)	0.0008 (9)
C15	0.0113 (11)	0.0123 (11)	0.0166 (11)	−0.0003 (8)	−0.0003 (8)	0.0031 (9)
C16	0.0128 (11)	0.0094 (11)	0.0190 (11)	−0.0002 (8)	0.0004 (9)	0.0009 (9)
C17	0.0113 (10)	0.0097 (11)	0.0103 (10)	0.0021 (8)	0.0018 (8)	0.0004 (8)
C18	0.0102 (10)	0.0116 (11)	0.0131 (10)	0.0008 (8)	0.0006 (8)	−0.0004 (8)
C19	0.0141 (11)	0.0079 (11)	0.0136 (10)	−0.0015 (8)	−0.0001 (8)	−0.0009 (8)
C20	0.0220 (13)	0.0149 (12)	0.0148 (11)	0.0026 (9)	0.0013 (9)	−0.0029 (9)
C21	0.0171 (13)	0.0168 (13)	0.0372 (16)	0.0029 (10)	−0.0089 (11)	−0.0057 (11)
C22	0.056 (2)	0.043 (2)	0.0170 (14)	0.0158 (16)	0.0132 (14)	−0.0017 (13)
C23	0.057 (2)	0.0350 (18)	0.0164 (13)	0.0177 (16)	−0.0076 (13)	−0.0072 (12)
C24	0.0120 (11)	0.0103 (11)	0.0127 (10)	0.0013 (8)	−0.0004 (8)	−0.0023 (8)

Zn1—O1	2.0353 (17)	C7—C6	1.381 (3)
Zn1—O3	2.1328 (17)	C7—H7	0.9300
Zn1—O4	2.2584 (17)	C9—C8	1.475 (3)
Zn1—O6	2.1393 (17)	C9—C10	1.394 (3)
Zn1—O7	2.0647 (17)	C9—C14	1.395 (3)
Zn1—N1	2.1307 (19)	C10—C11	1.376 (4)
Zn1—C8	2.545 (2)	C10—H10	0.9300
O1—C1	1.265 (3)	C11—H11	0.9300
O2—C1	1.265 (3)	C12—C11	1.410 (4)
O3—C8	1.278 (3)	C13—C12	1.410 (4)
O4—C8	1.271 (3)	C13—H13	0.9300
O5—C24	1.240 (3)	C14—C13	1.378 (4)
O6—H61	0.891 (17)	C14—H14	0.9300
O6—H62	0.879 (19)	C15—C16	1.389 (3)
O7—H71	0.89 (3)	C15—H15	0.9300
O7—H72	0.875 (18)	C16—C17	1.386 (3)
N1—C15	1.340 (3)	C16—H16	0.9300
N1—C19	1.345 (3)	C18—C17	1.392 (3)
N2—H21	0.89 (3)	C18—C19	1.382 (3)
N2—H22	0.89 (3)	C18—H18	0.9300
N3—C5	1.412 (3)	C19—H19	0.9300
N3—C20	1.463 (3)	C20—H20A	0.9600
N3—C21	1.458 (3)	C20—H20B	0.9600
N4—C12	1.368 (3)	C20—H20C	0.9600
N4—C22	1.448 (4)	C21—H21A	0.9600
N4—C23	1.449 (4)	C21—H21B	0.9600
C1—C2	1.495 (3)	C21—H21C	0.9600
C3—C2	1.391 (3)	C22—H22A	0.9600
C3—C4	1.389 (3)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600
C4—C5	1.398 (3)	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C6	1.404 (3)	C23—H23C	0.9600
C6—H6	0.9300	C24—N2	1.325 (3)
C7—C2	1.396 (3)	C24—C17	1.505 (3)
O1—Zn1—O3	158.68 (7)	C10—C9—C8	121.4 (2)
O1—Zn1—O4	99.43 (6)	C10—C9—C14	117.7 (2)
O1—Zn1—O6	91.08 (7)	C14—C9—C8	120.9 (2)
O1—Zn1—O7	106.57 (7)	C9—C10—H10	119.2
O1—Zn1—N1	89.59 (7)	C11—C10—C9	121.6 (2)
O3—Zn1—O4	60.03 (6)	C11—C10—H10	119.2
O3—Zn1—O6	93.40 (7)	C10—C11—C12	120.8 (3)
O6—Zn1—O4	87.44 (6)	C10—C11—H11	119.6
O7—Zn1—O3	94.72 (7)	C12—C11—H11	119.6
O7—Zn1—O4	151.55 (7)	N4—C12—C11	121.4 (3)
O7—Zn1—O6	80.80 (7)	N4—C12—C13	121.2 (3)
O7—Zn1—N1	89.90 (7)	C11—C12—C13	117.4 (2)
N1—Zn1—O3	89.40 (7)	C12—C13—H13	119.6
N1—Zn1—O4	101.82 (7)	C14—C13—C12	120.8 (2)
N1—Zn1—O6	170.47 (7)	C14—C13—H13	119.6
C1—O1—Zn1	128.40 (15)	C9—C14—H14	119.2
C8—O3—Zn1	93.10 (14)	C13—C14—C9	121.6 (3)
C8—O4—Zn1	87.63 (13)	C13—C14—H14	119.2
Zn1—O6—H61	98 (2)	N1—C15—C16	122.8 (2)
Zn1—O6—H62	111 (2)	N1—C15—H15	118.6
H61—O6—H62	106 (3)	C16—C15—H15	118.6
Zn1—O7—H71	119 (2)	C15—C16—H16	120.6
Zn1—O7—H72	130 (2)	C17—C16—C15	118.9 (2)
H72—O7—H71	106 (2)	C17—C16—H16	120.6
C15—N1—Zn1	123.02 (16)	C16—C17—C18	118.7 (2)
C15—N1—C19	117.8 (2)	C16—C17—C24	122.9 (2)
C19—N1—Zn1	119.03 (16)	C18—C17—C24	118.3 (2)
C24—N2—H21	116 (2)	C17—C18—H18	120.7
C24—N2—H22	126 (2)	C19—C18—C17	118.6 (2)
H22—N2—H21	118 (3)	C19—C18—H18	120.7
C5—N3—C21	116.7 (2)	N1—C19—C18	123.1 (2)
C5—N3—C20	116.3 (2)	N1—C19—H19	118.4
C21—N3—C20	112.2 (2)	C18—C19—H19	118.4
C12—N4—C22	120.3 (3)	N3—C20—H20A	109.5
C12—N4—C23	120.4 (3)	N3—C20—H20B	109.5
C22—N4—C23	119.1 (2)	N3—C20—H20C	109.5
O1—C1—O2	123.7 (2)	H20A—C20—H20B	109.5
O1—C1—C2	117.7 (2)	H20A—C20—H20C	109.5
O2—C1—C2	118.5 (2)	H20B—C20—H20C	109.5
C3—C2—C1	121.0 (2)	N3—C21—H21A	109.5
C3—C2—C7	117.9 (2)	N3—C21—H21B	109.5
C7—C2—C1	121.2 (2)	N3—C21—H21C	109.5
C2—C3—H3	119.4	H21A—C21—H21B	109.5
C4—C3—C2	121.3 (2)	H21A—C21—H21C	109.5
C4—C3—H3	119.4	H21B—C21—H21C	109.5
C3—C4—C5	120.9 (2)	N4—C22—H22A	109.5
C3—C4—H4	119.6	N4—C22—H22B	109.5
C5—C4—H4	119.6	N4—C22—H22C	109.5
C4—C5—N3	122.0 (2)	H22A—C22—H22B	109.5
C4—C5—C6	117.7 (2)	H22A—C22—H22C	109.5
C6—C5—N3	120.2 (2)	H22B—C22—H22C	109.5
C5—C6—H6	119.5	N4—C23—H23A	109.5
C7—C6—C5	121.0 (2)	N4—C23—H23B	109.5
C7—C6—H6	119.5	N4—C23—H23C	109.5
C2—C7—H7	119.3	H23A—C23—H23B	109.5
C6—C7—C2	121.3 (2)	H23A—C23—H23C	109.5
C6—C7—H7	119.3	H23B—C23—H23C	109.5
O3—C8—C9	119.8 (2)	O5—C24—N2	123.0 (2)
O4—C8—O3	119.2 (2)	O5—C24—C17	119.1 (2)
O4—C8—C9	121.0 (2)	N2—C24—C17	117.9 (2)
O3—Zn1—O1—C1	−71.5 (3)	C23—N4—C12—C13	−173.5 (3)
O4—Zn1—O1—C1	−56.9 (2)	O1—C1—C2—C3	−174.7 (2)
O6—Zn1—O1—C1	30.69 (19)	O1—C1—C2—C7	3.5 (3)
O7—Zn1—O1—C1	111.42 (19)	O2—C1—C2—C3	6.0 (3)
N1—Zn1—O1—C1	−158.81 (19)	O2—C1—C2—C7	−175.8 (2)
O1—Zn1—O3—C8	16.4 (2)	C4—C3—C2—C1	178.5 (2)
O4—Zn1—O3—C8	−0.36 (12)	C4—C3—C2—C7	0.3 (3)
O6—Zn1—O3—C8	−85.43 (13)	C2—C3—C4—C5	0.0 (4)
O7—Zn1—O3—C8	−166.47 (13)	C3—C4—C5—N3	−176.2 (2)
N1—Zn1—O3—C8	103.68 (13)	C3—C4—C5—C6	0.2 (3)
O1—Zn1—O4—C8	−173.56 (13)	N3—C5—C6—C7	175.8 (2)
O3—Zn1—O4—C8	0.36 (12)	C4—C5—C6—C7	−0.7 (3)
O6—Zn1—O4—C8	95.77 (13)	C6—C7—C2—C1	−179.0 (2)
O7—Zn1—O4—C8	30.5 (2)	C6—C7—C2—C3	−0.8 (3)
N1—Zn1—O4—C8	−81.99 (13)	C2—C7—C6—C5	1.0 (4)
O1—Zn1—N1—C15	22.18 (18)	C10—C9—C8—O3	0.2 (3)
O1—Zn1—N1—C19	−153.57 (17)	C10—C9—C8—O4	179.2 (2)
O3—Zn1—N1—C15	−136.52 (18)	C14—C9—C8—O3	−179.1 (2)
O3—Zn1—N1—C19	47.73 (17)	C14—C9—C8—O4	−0.1 (3)
O4—Zn1—N1—C19	106.89 (17)	C8—C9—C10—C11	−178.9 (2)
O4—Zn1—N1—C15	−77.36 (18)	C14—C9—C10—C11	0.4 (4)
O7—Zn1—N1—C15	128.76 (18)	C8—C9—C14—C13	178.0 (2)
O7—Zn1—N1—C19	−46.99 (17)	C10—C9—C14—C13	−1.3 (4)
Zn1—O1—C1—O2	−19.5 (3)	C9—C10—C11—C12	1.1 (4)
Zn1—O1—C1—C2	161.36 (15)	N4—C12—C11—C10	178.1 (3)
Zn1—O3—C8—O4	0.6 (2)	C13—C12—C11—C10	−1.7 (4)
Zn1—O3—C8—C9	179.65 (18)	C14—C13—C12—N4	−179.0 (2)
Zn1—O4—C8—O3	−0.6 (2)	C14—C13—C12—C11	0.8 (4)
Zn1—O4—C8—C9	−179.61 (19)	C9—C14—C13—C12	0.8 (4)
Zn1—N1—C15—C16	−175.38 (17)	N1—C15—C16—C17	1.3 (4)
C19—N1—C15—C16	0.4 (3)	C15—C16—C17—C18	−1.2 (3)
Zn1—N1—C19—C18	173.64 (17)	C15—C16—C17—C24	175.2 (2)
C15—N1—C19—C18	−2.3 (3)	C19—C18—C17—C16	−0.5 (3)
C20—N3—C5—C4	−146.3 (2)	C19—C18—C17—C24	−177.2 (2)
C20—N3—C5—C6	37.4 (3)	C17—C18—C19—N1	2.4 (3)
C21—N3—C5—C4	−10.4 (3)	O5—C24—C17—C16	−150.0 (2)
C21—N3—C5—C6	173.4 (2)	O5—C24—C17—C18	26.5 (3)
C22—N4—C12—C11	−178.3 (3)	N2—C24—C17—C16	30.0 (3)
C22—N4—C12—C13	1.5 (4)	N2—C24—C17—C18	−153.5 (2)
C23—N4—C12—C11	6.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O4i	0.89 (3)	2.15 (3)	3.034 (3)	174 (3)
N2—H22···O3ii	0.89 (3)	1.95 (3)	2.820 (3)	164 (3)
O6—H61···O2	0.89 (3)	1.79 (3)	2.646 (2)	161 (3)
O6—H62···O5iii	0.88 (3)	1.88 (3)	2.749 (2)	169 (3)
O7—H71···N3iv	0.89 (3)	2.01 (3)	2.863 (3)	162 (3)
O7—H72···O2v	0.87 (3)	1.80 (3)	2.667 (2)	171 (3)
C22—H22A···Cg3vi	0.96	2.74	3.567 (3)	145
C23—H23C···Cg2vii	0.96	2.86	3.644 (3)	140

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0353 (17)
Zn1—O3	2.1328 (17)
Zn1—O4	2.2584 (17)
Zn1—O6	2.1393 (17)
Zn1—O7	2.0647 (17)
Zn1—N1	2.1307 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O4i	0.89 (3)	2.15 (3)	3.034 (3)	174 (3)
N2—H22⋯O3ii	0.89 (3)	1.95 (3)	2.820 (3)	164 (3)
O6—H61⋯O2	0.89 (3)	1.79 (3)	2.646 (2)	161 (3)
O6—H62⋯O5iii	0.88 (3)	1.88 (3)	2.749 (2)	169 (3)
O7—H71⋯N3iv	0.89 (3)	2.01 (3)	2.863 (3)	162 (3)
O7—H72⋯O2v	0.87 (3)	1.80 (3)	2.667 (2)	171 (3)
C22—H22A⋯Cg3vi	0.96	2.74	3.567 (3)	145
C23—H23C⋯Cg2vii	0.96	2.86	3.644 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg2 and Cg3 are the centroids of the C9–C14 and N1/C15–C19 rings, respectively.