Aqua-(benzene-1,2-dicarboxyl-ato-κO)bis-[2-(1H-pyrazol-3-yl-κN)pyridine-κN]cadmium(II).

In the mononuclear title complex, [Cd(C(8)H(4)O(4))(C(8)H(7)N(3))(2)(H(2)O)], the Cd(II) atom is six-coordinated in a distorted octa-hedral geometry by four N atoms from two bidentate chelating 2-(1H-pyrazol-3-yl)pyridine ligands, one O atom from a benzene-1,2-dicarboxyl-ate ligand and one water mol-ecule. The mol-ecular structure features intra-molecular O-H⋯O and N-H⋯O hydrogen bonds. In the crystal structure, the complex mol-ecules are assembled into a two-dimensional supra-molecular layer parallel to (011) via O-H⋯O and N-H⋯O hydrogen bonds and π-π stacking inter-actions between the pyridyl and pyrazole rings [centroid-centroid distances = 3.544 (2) and 3.722 (3) Å].

Related literature

For general background to the roles played by aromatic ring stacking and hydrogen bonding in biological reactions and in mol­ecular recognition and self-organization, see: Borrows et al. (1995 ▶); Hunter (1994 ▶). For related structures, see: Cheng et al. (2006 ▶); Hu et al. (2008 ▶); Wan et al. (2003 ▶).

Experimental

Crystal data

[Cd(C8H4O4)(C8H7N3)2(H2O)]

M = 584.86

Triclinic,

a = 10.1546 (7) Å

b = 10.7709 (7) Å

c = 12.4900 (9) Å

α = 64.986 (1)°

β = 71.209 (1)°

γ = 81.618 (1)°

V = 1171.90 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.98 mm−1

T = 296 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.771, T max = 0.828

5869 measured reflections

4075 independent reflections

3194 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.064

S = 1.06

4075 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.60 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034616/hy2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034616/hy2347Isup2.hkl

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

[Cd(C8H4O4)(C8H7N3)2(H2O)]	Z = 2
Mr = 584.86	F(000) = 588
Triclinic, P1	Dx = 1.657 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1546 (7) Å	Cell parameters from 2320 reflections
b = 10.7709 (7) Å	θ = 2.4–26.3°
c = 12.4900 (9) Å	µ = 0.98 mm−1
α = 64.986 (1)°	T = 296 K
β = 71.209 (1)°	Block, colorless
γ = 81.618 (1)°	0.28 × 0.22 × 0.20 mm
V = 1171.90 (14) Å3

Bruker APEXII CCD diffractometer	4075 independent reflections
Radiation source: fine-focus sealed tube	3194 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.771, Tmax = 0.828	k = −11→12
5869 measured reflections	l = −14→12

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0213P)2 + 0.3676P] where P = (Fo2 + 2Fc2)/3
4075 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

	x	y	z	Uiso*/Ueq
Cd1	0.24772 (3)	0.29292 (3)	0.32881 (3)	0.03231 (10)
O1	0.1867 (3)	0.2927 (3)	0.5234 (2)	0.0476 (7)
O2	0.3783 (3)	0.3400 (3)	0.5504 (2)	0.0436 (7)
O3	0.3964 (3)	0.0332 (3)	0.6592 (3)	0.0526 (7)
O4	0.4584 (3)	−0.0169 (3)	0.8281 (2)	0.0553 (8)
O5	0.4235 (3)	0.1523 (3)	0.3978 (2)	0.0518 (7)
H5A	0.4793	0.0992	0.3694	0.078*
H5B	0.4031	0.1299	0.4751	0.078*
N1	0.0044 (3)	0.2749 (3)	0.3848 (3)	0.0356 (7)
N2	0.1955 (3)	0.1179 (3)	0.2898 (3)	0.0335 (7)
N3	0.2667 (3)	0.0223 (3)	0.2516 (3)	0.0414 (8)
H3A	0.3558	0.0203	0.2226	0.050*
N4	0.2559 (3)	0.4476 (3)	0.1084 (3)	0.0391 (8)
N5	0.3742 (3)	0.4808 (3)	0.2559 (3)	0.0337 (7)
N6	0.4404 (3)	0.5217 (3)	0.3126 (3)	0.0428 (8)
H6	0.4467	0.4744	0.3861	0.051*
C1	−0.0887 (4)	0.3532 (4)	0.4319 (4)	0.0483 (11)
H1	−0.0561	0.4242	0.4401	0.058*
C2	−0.2294 (5)	0.3350 (5)	0.4689 (4)	0.0587 (12)
H2	−0.2909	0.3935	0.4993	0.070*
C3	−0.2772 (4)	0.2280 (5)	0.4598 (4)	0.0601 (13)
H3	−0.3722	0.2125	0.4851	0.072*
C4	−0.1854 (4)	0.1449 (4)	0.4138 (3)	0.0453 (11)
H4	−0.2169	0.0719	0.4077	0.054*
C5	−0.0440 (4)	0.1701 (4)	0.3760 (3)	0.0330 (9)
C6	0.0611 (4)	0.0854 (4)	0.3267 (3)	0.0324 (9)
C7	0.0489 (4)	−0.0336 (4)	0.3124 (3)	0.0452 (11)
H7	−0.0324	−0.0786	0.3316	0.054*
C8	0.1816 (5)	−0.0697 (4)	0.2642 (4)	0.0462 (11)
H8	0.2082	−0.1450	0.2437	0.055*
C9	0.1999 (5)	0.4256 (5)	0.0353 (4)	0.0578 (12)
H9	0.1482	0.3466	0.0681	0.069*
C10	0.2141 (5)	0.5130 (5)	−0.0862 (4)	0.0635 (13)
H10	0.1728	0.4939	−0.1340	0.076*
C11	0.2908 (4)	0.6286 (5)	−0.1340 (4)	0.0579 (12)
H11	0.3027	0.6895	−0.2158	0.069*
C12	0.3501 (4)	0.6549 (4)	−0.0614 (3)	0.0431 (10)
H12	0.4024	0.7333	−0.0931	0.052*
C13	0.3305 (3)	0.5622 (3)	0.0601 (3)	0.0312 (9)
C14	0.3906 (4)	0.5814 (3)	0.1437 (3)	0.0313 (8)
C15	0.4666 (4)	0.6870 (4)	0.1304 (4)	0.0485 (11)
H15	0.4923	0.7688	0.0615	0.058*
C16	0.4951 (4)	0.6451 (4)	0.2400 (4)	0.0529 (12)
H16	0.5442	0.6941	0.2604	0.064*
C17	0.2603 (4)	0.2903 (3)	0.5888 (3)	0.0330 (9)
C18	0.1943 (3)	0.2270 (3)	0.7271 (3)	0.0284 (8)
C19	0.0726 (4)	0.2855 (4)	0.7768 (3)	0.0423 (10)
H19	0.0285	0.3548	0.7243	0.051*
C20	0.0159 (4)	0.2427 (4)	0.9027 (4)	0.0514 (11)
H20	−0.0655	0.2833	0.9347	0.062*
C21	0.0796 (4)	0.1403 (4)	0.9804 (4)	0.0523 (11)
H21	0.0423	0.1121	1.0655	0.063*
C22	0.1987 (4)	0.0793 (4)	0.9329 (3)	0.0434 (10)
H22	0.2414	0.0099	0.9866	0.052*
C23	0.2569 (3)	0.1189 (3)	0.8060 (3)	0.0288 (8)
C24	0.3806 (4)	0.0414 (4)	0.7593 (4)	0.0365 (9)

	U11	U22	U33	U12	U13	U23
Cd1	0.03555 (16)	0.02947 (15)	0.03196 (15)	−0.00863 (11)	−0.01207 (12)	−0.00811 (11)
O1	0.0392 (16)	0.0718 (19)	0.0339 (15)	−0.0109 (14)	−0.0121 (13)	−0.0188 (14)
O2	0.0391 (15)	0.0525 (17)	0.0334 (14)	−0.0165 (13)	−0.0063 (12)	−0.0098 (13)
O3	0.0638 (19)	0.0536 (18)	0.0454 (17)	0.0198 (14)	−0.0187 (15)	−0.0289 (15)
O4	0.0462 (17)	0.068 (2)	0.0481 (17)	0.0108 (15)	−0.0218 (15)	−0.0174 (15)
O5	0.0597 (18)	0.0574 (18)	0.0525 (17)	0.0234 (14)	−0.0305 (15)	−0.0327 (15)
N1	0.0378 (18)	0.0329 (18)	0.0318 (17)	−0.0021 (15)	−0.0107 (15)	−0.0080 (15)
N2	0.0373 (18)	0.0305 (17)	0.0340 (18)	−0.0020 (15)	−0.0107 (15)	−0.0134 (15)
N3	0.043 (2)	0.042 (2)	0.041 (2)	0.0027 (16)	−0.0156 (17)	−0.0165 (17)
N4	0.0442 (19)	0.0408 (19)	0.0325 (18)	−0.0096 (16)	−0.0151 (16)	−0.0092 (15)
N5	0.0397 (18)	0.0361 (17)	0.0258 (16)	−0.0100 (14)	−0.0106 (14)	−0.0089 (15)
N6	0.053 (2)	0.045 (2)	0.0325 (18)	−0.0139 (17)	−0.0164 (16)	−0.0110 (16)
C1	0.057 (3)	0.036 (2)	0.043 (2)	0.001 (2)	−0.012 (2)	−0.010 (2)
C2	0.050 (3)	0.058 (3)	0.054 (3)	0.016 (2)	−0.008 (2)	−0.020 (2)
C3	0.032 (2)	0.083 (4)	0.052 (3)	0.001 (3)	−0.013 (2)	−0.014 (3)
C4	0.037 (2)	0.055 (3)	0.040 (2)	−0.010 (2)	−0.016 (2)	−0.010 (2)
C5	0.038 (2)	0.032 (2)	0.0241 (19)	−0.0078 (18)	−0.0155 (17)	0.0004 (17)
C6	0.037 (2)	0.033 (2)	0.0236 (19)	−0.0105 (18)	−0.0107 (17)	−0.0037 (17)
C7	0.059 (3)	0.040 (2)	0.041 (2)	−0.020 (2)	−0.019 (2)	−0.011 (2)
C8	0.068 (3)	0.033 (2)	0.042 (2)	−0.005 (2)	−0.022 (2)	−0.014 (2)
C9	0.067 (3)	0.064 (3)	0.048 (3)	−0.022 (2)	−0.021 (2)	−0.017 (2)
C10	0.072 (3)	0.087 (4)	0.045 (3)	−0.011 (3)	−0.030 (3)	−0.026 (3)
C11	0.063 (3)	0.068 (3)	0.030 (2)	0.004 (3)	−0.020 (2)	−0.006 (2)
C12	0.046 (2)	0.042 (2)	0.032 (2)	−0.0029 (19)	−0.0107 (19)	−0.0053 (19)
C13	0.0270 (19)	0.032 (2)	0.0267 (19)	0.0024 (16)	−0.0052 (16)	−0.0075 (17)
C14	0.033 (2)	0.030 (2)	0.027 (2)	−0.0046 (17)	−0.0037 (17)	−0.0100 (17)
C15	0.058 (3)	0.039 (2)	0.042 (2)	−0.022 (2)	−0.009 (2)	−0.007 (2)
C16	0.063 (3)	0.047 (3)	0.051 (3)	−0.028 (2)	−0.008 (2)	−0.019 (2)
C17	0.042 (2)	0.029 (2)	0.028 (2)	−0.0002 (18)	−0.0095 (19)	−0.0121 (17)
C18	0.030 (2)	0.030 (2)	0.0287 (19)	−0.0084 (16)	−0.0068 (17)	−0.0146 (17)
C19	0.046 (2)	0.037 (2)	0.037 (2)	0.0019 (19)	−0.010 (2)	−0.0114 (19)
C20	0.048 (3)	0.056 (3)	0.045 (3)	0.006 (2)	0.000 (2)	−0.028 (2)
C21	0.062 (3)	0.059 (3)	0.027 (2)	−0.005 (2)	0.001 (2)	−0.017 (2)
C22	0.051 (3)	0.043 (2)	0.028 (2)	0.000 (2)	−0.010 (2)	−0.0078 (19)
C23	0.031 (2)	0.0283 (19)	0.030 (2)	−0.0057 (16)	−0.0089 (17)	−0.0122 (17)
C24	0.041 (2)	0.028 (2)	0.035 (2)	−0.0080 (18)	−0.006 (2)	−0.0080 (18)

Cd1—N5	2.241 (3)	C4—H4	0.9300
Cd1—N2	2.304 (3)	C5—C6	1.456 (5)
Cd1—O1	2.306 (3)	C6—C7	1.394 (5)
Cd1—O5	2.306 (2)	C7—C8	1.360 (5)
Cd1—N1	2.355 (3)	C7—H7	0.9300
Cd1—N4	2.525 (3)	C8—H8	0.9300
O1—C17	1.263 (4)	C9—C10	1.378 (6)
O2—C17	1.246 (4)	C9—H9	0.9300
O3—C24	1.248 (4)	C10—C11	1.367 (6)
O4—C24	1.262 (4)	C10—H10	0.9300
O5—H5A	0.8500	C11—C12	1.372 (5)
O5—H5B	0.8500	C11—H11	0.9300
N1—C1	1.334 (5)	C12—C13	1.387 (5)
N1—C5	1.352 (4)	C12—H12	0.9300
N2—N3	1.336 (4)	C13—C14	1.461 (5)
N2—C6	1.340 (4)	C14—C15	1.389 (5)
N3—C8	1.336 (4)	C15—C16	1.363 (5)
N3—H3A	0.8600	C15—H15	0.9300
N4—C9	1.331 (5)	C16—H16	0.9300
N4—C13	1.345 (4)	C17—C18	1.513 (5)
N5—C14	1.336 (4)	C18—C19	1.385 (5)
N5—N6	1.343 (4)	C18—C23	1.395 (5)
N6—C16	1.329 (4)	C19—C20	1.377 (5)
N6—H6	0.8600	C19—H19	0.9300
C1—C2	1.369 (5)	C20—C21	1.367 (5)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.373 (6)	C21—C22	1.372 (5)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.360 (6)	C22—C23	1.394 (5)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.389 (5)	C23—C24	1.500 (5)
N5—Cd1—N2	146.39 (10)	C8—C7—C6	105.2 (3)
N5—Cd1—O1	89.21 (9)	C8—C7—H7	127.4
N2—Cd1—O1	123.55 (9)	C6—C7—H7	127.4
N5—Cd1—O5	91.79 (10)	N3—C8—C7	107.9 (4)
N2—Cd1—O5	86.61 (10)	N3—C8—H8	126.1
O1—Cd1—O5	81.39 (9)	C7—C8—H8	126.1
N5—Cd1—N1	128.46 (10)	N4—C9—C10	123.9 (4)
N2—Cd1—N1	70.85 (11)	N4—C9—H9	118.1
O1—Cd1—N1	79.65 (10)	C10—C9—H9	118.1
O5—Cd1—N1	134.70 (10)	C11—C10—C9	117.8 (4)
N5—Cd1—N4	67.54 (10)	C11—C10—H10	121.1
N2—Cd1—N4	86.92 (10)	C9—C10—H10	121.1
O1—Cd1—N4	141.67 (10)	C10—C11—C12	120.0 (4)
O5—Cd1—N4	127.21 (10)	C10—C11—H11	120.0
N1—Cd1—N4	91.24 (10)	C12—C11—H11	120.0
C17—O1—Cd1	131.2 (2)	C11—C12—C13	118.7 (4)
Cd1—O5—H5A	130.4	C11—C12—H12	120.7
Cd1—O5—H5B	107.9	C13—C12—H12	120.7
H5A—O5—H5B	116.4	N4—C13—C12	122.0 (3)
C1—N1—C5	117.7 (3)	N4—C13—C14	115.6 (3)
C1—N1—Cd1	125.5 (3)	C12—C13—C14	122.4 (3)
C5—N1—Cd1	116.6 (2)	N5—C14—C15	110.1 (3)
N3—N2—C6	105.9 (3)	N5—C14—C13	117.4 (3)
N3—N2—Cd1	136.5 (2)	C15—C14—C13	132.5 (3)
C6—N2—Cd1	117.0 (2)	C16—C15—C14	105.1 (3)
C8—N3—N2	111.2 (3)	C16—C15—H15	127.4
C8—N3—H3A	124.4	C14—C15—H15	127.4
N2—N3—H3A	124.4	N6—C16—C15	108.0 (3)
C9—N4—C13	117.6 (3)	N6—C16—H16	126.0
C9—N4—Cd1	127.5 (3)	C15—C16—H16	126.0
C13—N4—Cd1	114.9 (2)	O2—C17—O1	126.4 (3)
C14—N5—N6	105.8 (3)	O2—C17—C18	117.4 (3)
C14—N5—Cd1	124.4 (2)	O1—C17—C18	116.1 (3)
N6—N5—Cd1	129.7 (2)	C19—C18—C23	119.4 (3)
C16—N6—N5	111.1 (3)	C19—C18—C17	118.2 (3)
C16—N6—H6	124.5	C23—C18—C17	122.3 (3)
N5—N6—H6	124.5	C20—C19—C18	121.0 (4)
N1—C1—C2	123.7 (4)	C20—C19—H19	119.5
N1—C1—H1	118.2	C18—C19—H19	119.5
C2—C1—H1	118.2	C21—C20—C19	119.9 (4)
C1—C2—C3	118.1 (4)	C21—C20—H20	120.1
C1—C2—H2	121.0	C19—C20—H20	120.1
C3—C2—H2	121.0	C20—C21—C22	119.9 (4)
C4—C3—C2	119.9 (4)	C20—C21—H21	120.0
C4—C3—H3	120.1	C22—C21—H21	120.0
C2—C3—H3	120.1	C21—C22—C23	121.4 (4)
C3—C4—C5	119.2 (4)	C21—C22—H22	119.3
C3—C4—H4	120.4	C23—C22—H22	119.3
C5—C4—H4	120.4	C22—C23—C18	118.3 (3)
N1—C5—C4	121.4 (4)	C22—C23—C24	119.2 (3)
N1—C5—C6	115.9 (3)	C18—C23—C24	122.5 (3)
C4—C5—C6	122.6 (3)	O3—C24—O4	124.5 (4)
N2—C6—C7	109.8 (3)	O3—C24—C23	118.6 (3)
N2—C6—C5	119.2 (3)	O4—C24—C23	116.8 (3)
C7—C6—C5	131.0 (3)
N5—Cd1—O1—C17	−56.3 (3)	C3—C4—C5—N1	0.5 (5)
N2—Cd1—O1—C17	115.7 (3)	C3—C4—C5—C6	179.5 (3)
O5—Cd1—O1—C17	35.6 (3)	N3—N2—C6—C7	0.7 (4)
N1—Cd1—O1—C17	174.3 (3)	Cd1—N2—C6—C7	−171.7 (2)
N4—Cd1—O1—C17	−107.0 (3)	N3—N2—C6—C5	178.9 (3)
N5—Cd1—N1—C1	−31.9 (3)	Cd1—N2—C6—C5	6.6 (4)
N2—Cd1—N1—C1	179.9 (3)	N1—C5—C6—N2	−2.3 (5)
O1—Cd1—N1—C1	48.7 (3)	C4—C5—C6—N2	178.6 (3)
O5—Cd1—N1—C1	115.5 (3)	N1—C5—C6—C7	175.5 (4)
N4—Cd1—N1—C1	−93.8 (3)	C4—C5—C6—C7	−3.6 (6)
N5—Cd1—N1—C5	152.8 (2)	N2—C6—C7—C8	−0.6 (4)
N2—Cd1—N1—C5	4.6 (2)	C5—C6—C7—C8	−178.6 (4)
O1—Cd1—N1—C5	−126.5 (2)	N2—N3—C8—C7	0.1 (4)
O5—Cd1—N1—C5	−59.8 (3)	C6—C7—C8—N3	0.3 (4)
N4—Cd1—N1—C5	90.9 (2)	C13—N4—C9—C10	0.0 (7)
N5—Cd1—N2—N3	53.0 (4)	Cd1—N4—C9—C10	−177.2 (3)
O1—Cd1—N2—N3	−112.4 (3)	N4—C9—C10—C11	0.3 (7)
O5—Cd1—N2—N3	−35.1 (3)	C9—C10—C11—C12	−0.3 (7)
N1—Cd1—N2—N3	−175.1 (3)	C10—C11—C12—C13	0.0 (6)
N4—Cd1—N2—N3	92.5 (3)	C9—N4—C13—C12	−0.3 (5)
N5—Cd1—N2—C6	−137.6 (2)	Cd1—N4—C13—C12	177.2 (3)
O1—Cd1—N2—C6	56.9 (3)	C9—N4—C13—C14	−179.6 (3)
O5—Cd1—N2—C6	134.2 (2)	Cd1—N4—C13—C14	−2.1 (4)
N1—Cd1—N2—C6	−5.8 (2)	C11—C12—C13—N4	0.3 (6)
N4—Cd1—N2—C6	−98.2 (2)	C11—C12—C13—C14	179.5 (4)
C6—N2—N3—C8	−0.5 (4)	N6—N5—C14—C15	−0.7 (4)
Cd1—N2—N3—C8	169.6 (3)	Cd1—N5—C14—C15	175.8 (2)
N5—Cd1—N4—C9	177.2 (4)	N6—N5—C14—C13	178.7 (3)
N2—Cd1—N4—C9	19.5 (3)	Cd1—N5—C14—C13	−4.8 (4)
O1—Cd1—N4—C9	−126.0 (3)	N4—C13—C14—N5	4.3 (5)
O5—Cd1—N4—C9	102.9 (3)	C12—C13—C14—N5	−175.0 (3)
N1—Cd1—N4—C9	−51.2 (4)	N4—C13—C14—C15	−176.5 (4)
N5—Cd1—N4—C13	−0.1 (2)	C12—C13—C14—C15	4.3 (6)
N2—Cd1—N4—C13	−157.7 (3)	N5—C14—C15—C16	0.0 (5)
O1—Cd1—N4—C13	56.8 (3)	C13—C14—C15—C16	−179.2 (4)
O5—Cd1—N4—C13	−74.3 (3)	N5—N6—C16—C15	−1.1 (5)
N1—Cd1—N4—C13	131.5 (2)	C14—C15—C16—N6	0.6 (5)
N2—Cd1—N5—C14	46.0 (4)	Cd1—O1—C17—O2	30.6 (6)
O1—Cd1—N5—C14	−146.1 (3)	Cd1—O1—C17—C18	−152.7 (2)
O5—Cd1—N5—C14	132.5 (3)	O2—C17—C18—C19	116.8 (4)
N1—Cd1—N5—C14	−70.0 (3)	O1—C17—C18—C19	−60.2 (4)
N4—Cd1—N5—C14	2.6 (3)	O2—C17—C18—C23	−58.5 (5)
N2—Cd1—N5—N6	−138.4 (3)	O1—C17—C18—C23	124.5 (4)
O1—Cd1—N5—N6	29.5 (3)	C23—C18—C19—C20	2.8 (5)
O5—Cd1—N5—N6	−51.8 (3)	C17—C18—C19—C20	−172.6 (4)
N1—Cd1—N5—N6	105.6 (3)	C18—C19—C20—C21	−0.4 (6)
N4—Cd1—N5—N6	178.2 (3)	C19—C20—C21—C22	−0.9 (7)
C14—N5—N6—C16	1.1 (4)	C20—C21—C22—C23	−0.2 (6)
Cd1—N5—N6—C16	−175.2 (3)	C21—C22—C23—C18	2.6 (5)
C5—N1—C1—C2	−1.5 (6)	C21—C22—C23—C24	−175.2 (3)
Cd1—N1—C1—C2	−176.7 (3)	C19—C18—C23—C22	−3.8 (5)
N1—C1—C2—C3	1.7 (6)	C17—C18—C23—C22	171.4 (3)
C1—C2—C3—C4	−0.7 (7)	C19—C18—C23—C24	173.9 (3)
C2—C3—C4—C5	−0.3 (6)	C17—C18—C23—C24	−10.8 (5)
C1—N1—C5—C4	0.4 (5)	C22—C23—C24—O3	149.6 (3)
Cd1—N1—C5—C4	176.0 (3)	C18—C23—C24—O3	−28.2 (5)
C1—N1—C5—C6	−178.7 (3)	C22—C23—C24—O4	−27.2 (5)
Cd1—N1—C5—C6	−3.1 (4)	C18—C23—C24—O4	155.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3i	0.85	1.84	2.672 (4)	168
O5—H5B···O3	0.85	2.07	2.892 (4)	164
N3—H3A···O4i	0.86	1.79	2.646 (4)	176
N6—H6···O2	0.86	1.91	2.700 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3i	0.85	1.84	2.672 (4)	168
O5—H5B⋯O3	0.85	2.07	2.892 (4)	164
N3—H3A⋯O4i	0.86	1.79	2.646 (4)	176
N6—H6⋯O2	0.86	1.91	2.700 (4)	152

Symmetry code: (i) .