Triaqua-(benzene-1,3-dicarboxyl-ato)(4,5-diaza-fluoren-9-one)cadmium(II) penta-hydrate.

In the title compound, [Cd(C(8)H(4)O(4))(C(11)H(6)N(2)O)(H(2)O)(3)]·5H(2)O, the Cd(II) atom is seven-coordinated by two N atoms from one bidentate phenanthroline-derived ligand and by five O atoms, two from one bidentate benzene-1,3-dicarboxyl-ate (1,3-BDC) ligand and three from water mol-ecules, in a distorted penta-gonal-bipyramidal geometry. Neighbouring units inter-act through π-π inter-actions [centroid-centroid distances = 3.380 (3) and 3.283 (4) Å]. Finally, three types of O-H⋯O hydrogen bonds exist between coordinated dissociative water mol-ecules and hybridization water mol-ecules and carboxyl-ate O atoms, resulting in a two-dimensional network parallel to (010).

Related literature

For applications of 1,10-phenanthroline and its derivatives in the construction of metal-organic complexes, see: Li et al. (2006 ▶, 2009 ▶); Olivier et al. (2008 ▶); Hong et al. (2009 ▶). For π–π stacking in related structures, see: Noveron et al. (2002 ▶). For the synthesis of 4,5-diaza­fluorene-9-one, see: Henderson et al. (1984 ▶).

Experimental

Crystal data

[Cd(C8H4O4)(C11H6N2O)(H2O)3]·5H2O

M = 602.83

Monoclinic,

a = 7.1218 (6) Å

b = 31.893 (3) Å

c = 11.0278 (9) Å

β = 106.579 (1)°

V = 2400.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 292 K

0.54 × 0.23 × 0.18 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.762, T max = 0.839

14040 measured reflections

4721 independent reflections

3839 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.119

S = 1.07

4721 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.81 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810045551/nk2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045551/nk2061Isup2.hkl

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

[Cd(C8H4O4)(C11H6N2O)(H2O)3]·5H2O	F(000) = 1224
Mr = 602.83	Dx = 1.665 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1218 (6) Å	θ = 2.0–26.3°
b = 31.893 (3) Å	µ = 0.98 mm−1
c = 11.0278 (9) Å	T = 292 K
β = 106.579 (1)°	Block, yellow
V = 2400.7 (4) Å3	0.54 × 0.23 × 0.18 mm
Z = 4

Bruker SMART diffractometer	4721 independent reflections
Radiation source: fine-focus sealed tube	3839 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 0 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −5→8
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −39→39
Tmin = 0.762, Tmax = 0.839	l = −13→13
14040 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0547P)2 + 1.8475P] where P = (Fo2 + 2Fc2)/3
4721 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.81 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	Occ. (<1)
Cd1	0.56424 (5)	0.130201 (10)	0.55013 (3)	0.02848 (13)
O1	0.7075 (5)	0.13446 (11)	0.7651 (3)	0.0416 (9)
OW1	0.8374 (4)	0.09822 (9)	0.5298 (3)	0.0312 (7)
HW1A	0.8890	0.1109	0.4809	0.037*
HW1B	0.9250	0.0942	0.5979	0.037*
O2	0.5183 (5)	0.07925 (12)	0.7288 (3)	0.0456 (9)
OW2	0.2993 (5)	0.16577 (13)	0.5563 (3)	0.0578 (12)
HW2A	0.2058	0.1667	0.4891	0.069*
HW2B	0.2668	0.1774	0.6207	0.069*
O3	0.9536 (5)	0.18494 (9)	1.2167 (3)	0.0336 (8)
OW3	0.7151 (6)	0.19952 (11)	0.5577 (3)	0.0515 (10)
HW3A	0.7787	0.2095	0.6338	0.062*
HW3B	0.7838	0.2084	0.5131	0.062*
O4	0.9934 (5)	0.13719 (10)	1.3685 (3)	0.0333 (8)
O5	0.1452 (5)	0.05436 (10)	−0.0081 (3)	0.0349 (8)
N1	0.4690 (5)	0.14857 (11)	0.3209 (3)	0.0259 (8)
N2	0.3800 (5)	0.07067 (11)	0.4391 (3)	0.0264 (8)
C1	0.4799 (7)	0.18203 (14)	0.2489 (5)	0.0333 (11)
H1	0.5383	0.2064	0.2889	0.040*
C2	0.4087 (7)	0.18207 (15)	0.1182 (5)	0.0359 (11)
H2A	0.4202	0.2062	0.0733	0.043*
C3	0.3204 (7)	0.14672 (15)	0.0531 (4)	0.0316 (10)
H3	0.2742	0.1462	−0.0347	0.038*
C4	0.3049 (6)	0.11249 (14)	0.1256 (4)	0.0263 (9)
C5	0.2193 (6)	0.06945 (14)	0.0947 (4)	0.0287 (10)
C6	0.2442 (6)	0.04832 (13)	0.2210 (4)	0.0245 (9)
C7	0.1839 (6)	0.01058 (14)	0.2564 (4)	0.0308 (10)
H7	0.1212	−0.0094	0.1972	0.037*
C8	0.2219 (7)	0.00387 (14)	0.3860 (4)	0.0334 (11)
H8	0.1813	−0.0210	0.4147	0.040*
C9	0.3191 (7)	0.03368 (14)	0.4727 (4)	0.0312 (10)
H9	0.3436	0.0278	0.5585	0.037*
C10	0.3391 (6)	0.07652 (13)	0.3142 (4)	0.0221 (9)
C11	0.3795 (6)	0.11571 (13)	0.2567 (4)	0.0243 (9)
C12	0.9333 (6)	0.14869 (14)	1.2546 (4)	0.0251 (9)
C13	0.8319 (6)	0.11616 (13)	1.1591 (4)	0.0234 (9)
C14	0.7805 (6)	0.12412 (13)	1.0307 (4)	0.0243 (9)
H14	0.8081	0.1503	1.0025	0.029*
C15	0.6886 (6)	0.09410 (14)	0.9428 (4)	0.0274 (10)
C16	0.6496 (7)	0.05520 (15)	0.9856 (5)	0.0338 (11)
H16	0.5879	0.0349	0.9274	0.041*
C17	0.7005 (7)	0.04609 (14)	1.1122 (5)	0.0337 (11)
H17	0.6737	0.0197	1.1393	0.040*
C18	0.7922 (6)	0.07636 (14)	1.2003 (4)	0.0285 (10)
H18	0.8271	0.0702	1.2863	0.034*
C19	0.6332 (6)	0.10307 (16)	0.8034 (4)	0.0321 (11)
OW4	0.1300 (5)	0.07422 (14)	0.7339 (3)	0.0625 (12)
HW4A	0.1331	0.0676	0.8169	0.075*
HW4B	0.2467	0.0716	0.7319	0.075*
OW5	0.2756 (7)	0.19371 (15)	0.7778 (4)	0.0766 (14)
HW5A	0.1698	0.1891	0.7959	0.092*
HW5B	0.3185	0.2198	0.8040	0.092*
OW6	0.3635 (6)	0.25918 (11)	0.5216 (3)	0.0536 (11)
HW6A	0.3927	0.2793	0.5723	0.064*
HW6B	0.4312	0.2386	0.5545	0.064*
OW7	0.9155 (6)	0.20440 (13)	0.8111 (3)	0.0589 (11)
HW7A	0.8662	0.1781	0.8182	0.071*
HW7B	0.8881	0.2207	0.8634	0.071*
OW8	0.4647 (6)	0.26328 (12)	0.9142 (4)	0.0279 (9)	0.75
HW8A	0.4693	0.2841	0.8685	0.033*	0.75
HW8B	0.5802	0.2546	0.9405	0.033*	0.75
OW8'	0.477 (2)	0.2319 (4)	1.0368 (17)	0.061 (5)	0.25
H8'	0.4158	0.2104	1.0082	0.073*	0.25
H8''	0.5963	0.2359	1.0493	0.073*	0.25

	U11	U22	U33	U12	U13	U23
Cd1	0.0292 (2)	0.03009 (19)	0.02268 (19)	0.00057 (15)	0.00189 (14)	−0.00493 (14)
O1	0.044 (2)	0.054 (2)	0.0225 (17)	−0.0072 (17)	0.0024 (16)	−0.0039 (15)
OW1	0.0296 (17)	0.0403 (18)	0.0240 (16)	−0.0001 (14)	0.0079 (14)	0.0083 (14)
O2	0.036 (2)	0.064 (2)	0.034 (2)	−0.0091 (18)	0.0051 (16)	−0.0191 (18)
OW2	0.034 (2)	0.092 (3)	0.036 (2)	0.028 (2)	−0.0080 (17)	−0.033 (2)
O3	0.044 (2)	0.0315 (17)	0.0209 (16)	−0.0052 (15)	0.0032 (15)	−0.0013 (13)
OW3	0.068 (3)	0.039 (2)	0.035 (2)	−0.0166 (19)	−0.0034 (19)	−0.0003 (16)
O4	0.0363 (19)	0.0418 (19)	0.0182 (16)	−0.0087 (15)	0.0019 (14)	0.0018 (13)
O5	0.0340 (18)	0.0456 (19)	0.0220 (17)	−0.0038 (15)	0.0032 (14)	−0.0081 (15)
N1	0.0227 (19)	0.0261 (18)	0.026 (2)	0.0014 (16)	0.0030 (16)	−0.0035 (16)
N2	0.0241 (19)	0.0296 (19)	0.0224 (19)	0.0020 (15)	0.0016 (16)	−0.0012 (15)
C1	0.033 (3)	0.026 (2)	0.044 (3)	−0.003 (2)	0.015 (2)	−0.002 (2)
C2	0.036 (3)	0.034 (3)	0.038 (3)	0.002 (2)	0.012 (2)	0.010 (2)
C3	0.032 (3)	0.037 (2)	0.027 (2)	0.006 (2)	0.011 (2)	0.005 (2)
C4	0.020 (2)	0.033 (2)	0.023 (2)	0.0041 (19)	0.0023 (18)	0.0000 (19)
C5	0.021 (2)	0.035 (2)	0.031 (3)	0.0055 (19)	0.009 (2)	−0.006 (2)
C6	0.021 (2)	0.030 (2)	0.021 (2)	0.0025 (18)	0.0029 (18)	−0.0022 (17)
C7	0.028 (2)	0.029 (2)	0.032 (3)	−0.0005 (19)	0.003 (2)	−0.007 (2)
C8	0.039 (3)	0.025 (2)	0.035 (3)	−0.003 (2)	0.009 (2)	0.005 (2)
C9	0.035 (3)	0.034 (2)	0.023 (2)	0.004 (2)	0.007 (2)	0.0049 (19)
C10	0.019 (2)	0.025 (2)	0.021 (2)	0.0022 (17)	0.0026 (17)	−0.0035 (17)
C11	0.017 (2)	0.029 (2)	0.027 (2)	0.0039 (18)	0.0060 (18)	0.0015 (18)
C12	0.016 (2)	0.038 (2)	0.022 (2)	0.0006 (19)	0.0060 (18)	−0.0037 (19)
C13	0.018 (2)	0.028 (2)	0.026 (2)	0.0011 (17)	0.0085 (18)	−0.0039 (18)
C14	0.021 (2)	0.028 (2)	0.025 (2)	0.0008 (18)	0.0085 (18)	−0.0035 (18)
C15	0.016 (2)	0.038 (2)	0.027 (2)	0.0002 (19)	0.0053 (18)	−0.006 (2)
C16	0.024 (2)	0.039 (3)	0.039 (3)	−0.007 (2)	0.009 (2)	−0.018 (2)
C17	0.033 (3)	0.030 (2)	0.040 (3)	−0.006 (2)	0.014 (2)	−0.001 (2)
C18	0.024 (2)	0.034 (2)	0.027 (2)	0.0000 (19)	0.0061 (19)	0.0018 (19)
C19	0.020 (2)	0.047 (3)	0.027 (2)	0.008 (2)	0.002 (2)	−0.010 (2)
OW4	0.035 (2)	0.115 (4)	0.034 (2)	−0.009 (2)	0.0048 (18)	0.020 (2)
OW5	0.085 (3)	0.096 (3)	0.061 (3)	−0.034 (3)	0.041 (3)	−0.030 (3)
OW6	0.090 (3)	0.0289 (18)	0.035 (2)	0.0020 (19)	0.008 (2)	0.0007 (15)
OW7	0.068 (3)	0.069 (3)	0.041 (2)	−0.021 (2)	0.018 (2)	−0.0136 (19)
OW8	0.036 (2)	0.0227 (19)	0.025 (2)	0.0051 (17)	0.0096 (19)	0.0136 (16)
OW8'	0.060 (10)	0.038 (8)	0.096 (14)	−0.021 (8)	0.040 (10)	0.007 (8)

Cd1—OW2	2.219 (3)	C6—C10	1.388 (6)
Cd1—OW1	2.264 (3)	C7—C8	1.394 (6)
Cd1—O1	2.302 (3)	C7—H7	0.9300
Cd1—N2	2.431 (4)	C8—C9	1.386 (6)
Cd1—OW3	2.449 (3)	C8—H8	0.9300
Cd1—N1	2.492 (4)	C9—H9	0.9300
Cd1—O2	2.645 (4)	C10—C11	1.467 (6)
O1—C19	1.260 (6)	C12—C13	1.508 (6)
OW1—HW1A	0.8387	C13—C14	1.381 (6)
OW1—HW1B	0.8379	C13—C18	1.404 (6)
O2—C19	1.241 (5)	C14—C15	1.386 (6)
OW2—HW2A	0.8440	C14—H14	0.9300
OW2—HW2B	0.8887	C15—C16	1.383 (7)
O3—C12	1.252 (5)	C15—C19	1.502 (6)
OW3—HW3A	0.8910	C16—C17	1.370 (7)
OW3—HW3B	0.8352	C16—H16	0.9300
O4—C12	1.259 (5)	C17—C18	1.393 (6)
O5—C5	1.206 (5)	C17—H17	0.9300
N1—C11	1.323 (6)	C18—H18	0.9300
N1—C1	1.346 (6)	OW4—HW4A	0.9335
N2—C10	1.336 (5)	OW4—HW4B	0.8417
N2—C9	1.345 (6)	OW5—HW5A	0.8459
C1—C2	1.385 (7)	OW5—HW5B	0.9059
C1—H1	0.9300	OW6—HW6A	0.8383
C2—C3	1.387 (7)	OW6—HW6B	0.8348
C2—H2A	0.9300	OW7—HW7A	0.9227
C3—C4	1.376 (6)	OW7—HW7B	0.8391
C3—H3	0.9300	OW8—OW8'	1.663 (16)
C4—C11	1.394 (6)	OW8—HW8A	0.8407
C4—C5	1.501 (6)	OW8—HW8B	0.8376
C5—C6	1.511 (6)	OW8'—H8'	0.8260
C6—C7	1.372 (6)	OW8'—H8''	0.8296
OW2—Cd1—OW1	174.63 (14)	C7—C6—C10	118.9 (4)
OW2—Cd1—O1	93.95 (13)	C7—C6—C5	133.6 (4)
OW1—Cd1—O1	89.31 (12)	C10—C6—C5	107.4 (4)
OW2—Cd1—N2	94.20 (13)	C6—C7—C8	116.2 (4)
OW1—Cd1—N2	87.35 (11)	C6—C7—H7	121.9
O1—Cd1—N2	125.57 (12)	C8—C7—H7	121.9
OW2—Cd1—OW3	84.62 (15)	C9—C8—C7	121.0 (4)
OW1—Cd1—OW3	91.66 (12)	C9—C8—H8	119.5
O1—Cd1—OW3	81.41 (12)	C7—C8—H8	119.5
N2—Cd1—OW3	152.96 (12)	N2—C9—C8	123.2 (4)
OW2—Cd1—N1	85.60 (13)	N2—C9—H9	118.4
OW1—Cd1—N1	89.90 (11)	C8—C9—H9	118.4
O1—Cd1—N1	160.53 (12)	N2—C10—C6	126.2 (4)
N2—Cd1—N1	73.81 (12)	N2—C10—C11	123.5 (4)
OW3—Cd1—N1	79.17 (12)	C6—C10—C11	110.2 (4)
OW2—Cd1—O2	90.23 (14)	N1—C11—C4	126.6 (4)
OW1—Cd1—O2	95.13 (11)	N1—C11—C10	124.6 (4)
O1—Cd1—O2	51.81 (11)	C4—C11—C10	108.8 (4)
N2—Cd1—O2	74.44 (11)	O3—C12—O4	124.3 (4)
OW3—Cd1—O2	132.49 (11)	O3—C12—C13	118.7 (4)
N1—Cd1—O2	147.56 (11)	O4—C12—C13	117.1 (4)
C19—O1—Cd1	101.1 (3)	C14—C13—C18	118.7 (4)
Cd1—OW1—HW1A	113.1	C14—C13—C12	121.6 (4)
Cd1—OW1—HW1B	114.9	C18—C13—C12	119.7 (4)
HW1A—OW1—HW1B	107.4	C13—C14—C15	121.6 (4)
C19—O2—Cd1	85.4 (3)	C13—C14—H14	119.2
Cd1—OW2—HW2A	117.1	C15—C14—H14	119.2
Cd1—OW2—HW2B	131.0	C16—C15—C14	118.8 (4)
HW2A—OW2—HW2B	111.6	C16—C15—C19	120.0 (4)
Cd1—OW3—HW3A	117.0	C14—C15—C19	121.2 (4)
Cd1—OW3—HW3B	127.6	C17—C16—C15	121.1 (4)
HW3A—OW3—HW3B	102.0	C17—C16—H16	119.4
C11—N1—C1	114.3 (4)	C15—C16—H16	119.4
C11—N1—Cd1	107.9 (3)	C16—C17—C18	120.0 (4)
C1—N1—Cd1	137.8 (3)	C16—C17—H17	120.0
C10—N2—C9	114.5 (4)	C18—C17—H17	120.0
C10—N2—Cd1	109.7 (3)	C17—C18—C13	119.9 (4)
C9—N2—Cd1	135.7 (3)	C17—C18—H18	120.1
N1—C1—C2	123.3 (4)	C13—C18—H18	120.1
N1—C1—H1	118.3	O2—C19—O1	121.7 (4)
C2—C1—H1	118.3	O2—C19—C15	119.6 (5)
C1—C2—C3	121.0 (4)	O1—C19—C15	118.8 (4)
C1—C2—H2A	119.5	HW4A—OW4—HW4B	104.8
C3—C2—H2A	119.5	HW5A—OW5—HW5B	109.1
C4—C3—C2	116.4 (4)	HW6A—OW6—HW6B	108.2
C4—C3—H3	121.8	HW7A—OW7—HW7B	109.6
C2—C3—H3	121.8	OW8'—OW8—HW8A	163.9
C3—C4—C11	118.3 (4)	OW8'—OW8—HW8B	72.6
C3—C4—C5	133.5 (4)	HW8A—OW8—HW8B	105.4
C11—C4—C5	108.2 (4)	OW8—OW8'—H8'	106.8
O5—C5—C4	128.2 (4)	OW8—OW8'—H8''	81.8
O5—C5—C6	126.4 (4)	H8'—OW8'—H8''	126.5
C4—C5—C6	105.4 (4)
OW2—Cd1—O1—C19	86.5 (3)	C4—C5—C6—C10	−1.2 (4)
OW1—Cd1—O1—C19	−97.7 (3)	C10—C6—C7—C8	0.8 (6)
N2—Cd1—O1—C19	−11.5 (3)	C5—C6—C7—C8	−174.3 (4)
OW3—Cd1—O1—C19	170.5 (3)	C6—C7—C8—C9	−1.4 (7)
N1—Cd1—O1—C19	174.5 (3)	C10—N2—C9—C8	0.0 (6)
O2—Cd1—O1—C19	−0.7 (3)	Cd1—N2—C9—C8	−176.4 (3)
OW2—Cd1—O2—C19	−94.2 (3)	C7—C8—C9—N2	1.0 (7)
OW1—Cd1—O2—C19	85.7 (3)	C9—N2—C10—C6	−0.6 (6)
O1—Cd1—O2—C19	0.7 (3)	Cd1—N2—C10—C6	176.7 (3)
N2—Cd1—O2—C19	171.5 (3)	C9—N2—C10—C11	175.5 (4)
OW3—Cd1—O2—C19	−11.3 (3)	Cd1—N2—C10—C11	−7.2 (5)
N1—Cd1—O2—C19	−176.3 (3)	C7—C6—C10—N2	0.2 (7)
OW2—Cd1—N1—C11	−99.8 (3)	C5—C6—C10—N2	176.5 (4)
OW1—Cd1—N1—C11	83.2 (3)	C7—C6—C10—C11	−176.3 (4)
O1—Cd1—N1—C11	170.8 (3)	C5—C6—C10—C11	0.0 (5)
N2—Cd1—N1—C11	−4.1 (3)	C1—N1—C11—C4	2.4 (6)
OW3—Cd1—N1—C11	174.9 (3)	Cd1—N1—C11—C4	−179.1 (4)
O2—Cd1—N1—C11	−16.3 (4)	C1—N1—C11—C10	−176.2 (4)
OW2—Cd1—N1—C1	78.2 (4)	Cd1—N1—C11—C10	2.3 (5)
OW1—Cd1—N1—C1	−98.9 (4)	C3—C4—C11—N1	−1.3 (7)
O1—Cd1—N1—C1	−11.2 (7)	C5—C4—C11—N1	179.0 (4)
N2—Cd1—N1—C1	173.9 (5)	C3—C4—C11—C10	177.5 (4)
OW3—Cd1—N1—C1	−7.2 (4)	C5—C4—C11—C10	−2.2 (5)
O2—Cd1—N1—C1	161.7 (4)	N2—C10—C11—N1	3.6 (7)
OW2—Cd1—N2—C10	89.9 (3)	C6—C10—C11—N1	−179.7 (4)
OW1—Cd1—N2—C10	−85.0 (3)	N2—C10—C11—C4	−175.2 (4)
O1—Cd1—N2—C10	−172.2 (3)	C6—C10—C11—C4	1.4 (5)
OW3—Cd1—N2—C10	3.5 (5)	O3—C12—C13—C14	7.0 (6)
N1—Cd1—N2—C10	5.7 (3)	O4—C12—C13—C14	−172.5 (4)
O2—Cd1—N2—C10	179.0 (3)	O3—C12—C13—C18	−174.5 (4)
OW2—Cd1—N2—C9	−93.6 (4)	O4—C12—C13—C18	5.9 (6)
OW1—Cd1—N2—C9	91.6 (4)	C18—C13—C14—C15	1.0 (6)
O1—Cd1—N2—C9	4.3 (5)	C12—C13—C14—C15	179.5 (4)
OW3—Cd1—N2—C9	−180.0 (4)	C13—C14—C15—C16	−0.6 (6)
N1—Cd1—N2—C9	−177.8 (4)	C13—C14—C15—C19	180.0 (4)
O2—Cd1—N2—C9	−4.5 (4)	C14—C15—C16—C17	−0.1 (7)
C11—N1—C1—C2	−1.6 (6)	C19—C15—C16—C17	179.3 (4)
Cd1—N1—C1—C2	−179.5 (3)	C15—C16—C17—C18	0.3 (7)
N1—C1—C2—C3	−0.1 (8)	C16—C17—C18—C13	0.1 (7)
C1—C2—C3—C4	1.2 (7)	C14—C13—C18—C17	−0.8 (6)
C2—C3—C4—C11	−0.6 (6)	C12—C13—C18—C17	−179.3 (4)
C2—C3—C4—C5	178.9 (5)	Cd1—O2—C19—O1	−1.1 (4)
C3—C4—C5—O5	2.2 (8)	Cd1—O2—C19—C15	179.9 (4)
C11—C4—C5—O5	−178.2 (4)	Cd1—O1—C19—O2	1.3 (5)
C3—C4—C5—C6	−177.5 (5)	Cd1—O1—C19—C15	−179.7 (3)
C11—C4—C5—C6	2.1 (5)	C16—C15—C19—O2	14.8 (6)
O5—C5—C6—C7	−5.5 (8)	C14—C15—C19—O2	−165.8 (4)
C4—C5—C6—C7	174.2 (5)	C16—C15—C19—O1	−164.2 (4)
O5—C5—C6—C10	179.0 (4)	C14—C15—C19—O1	15.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—HW1A···O4i	0.84	1.82	2.660 (4)	177
OW1—HW1B···OW4ii	0.84	1.88	2.705 (5)	168
OW2—HW2A···O4iii	0.84	1.95	2.700 (5)	148
OW3—HW3B···OW8iv	0.84	2.11	2.945 (6)	174
OW3—HW3A···OW7	0.89	1.93	2.756 (5)	154
OW5—HW5A···OW7v	0.85	1.93	2.714 (6)	154
OW4—HW4B···O2	0.84	1.96	2.787 (5)	167
OW6—HW6A···O3vi	0.84	1.90	2.725 (5)	166
OW7—HW7B···OW6vii	0.84	1.91	2.715 (5)	159
OW8—HW8A···O3vi	0.84	1.92	2.717 (5)	158
OW8—HW8A···O4vi	0.84	2.52	3.230 (5)	143
OW8—HW8B···OW6vii	0.84	2.01	2.839 (6)	172
OW6—HW6B···OW3	0.83	2.37	3.079 (5)	144
OW6—HW6B···OW2	0.83	2.51	3.055 (6)	124
OW7—HW7A···O1	0.92	1.78	2.646 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW1—HW1A⋯O4i	0.84	1.82	2.660 (4)	177
OW1—HW1B⋯OW4ii	0.84	1.88	2.705 (5)	168
OW2—HW2A⋯O4iii	0.84	1.95	2.700 (5)	148
OW3—HW3B⋯OW8iv	0.84	2.11	2.945 (6)	174
OW3—HW3A⋯OW7	0.89	1.93	2.756 (5)	154
OW5—HW5A⋯OW7v	0.85	1.93	2.714 (6)	154
OW4—HW4B⋯O2	0.84	1.96	2.787 (5)	167
OW6—HW6A⋯O3vi	0.84	1.90	2.725 (5)	166
OW7—HW7B⋯OW6vii	0.84	1.91	2.715 (5)	159
OW8—HW8A⋯O3vi	0.84	1.92	2.717 (5)	158
OW8—HW8A⋯O4vi	0.84	2.52	3.230 (5)	143
OW8—HW8B⋯OW6vii	0.84	2.01	2.839 (6)	172
OW6—HW6B⋯OW3	0.83	2.37	3.079 (5)	144
OW6—HW6B⋯OW2	0.83	2.51	3.055 (6)	124
OW7—HW7A⋯O1	0.92	1.78	2.646 (5)	155

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