Poly[[(μ-3,4-dicarboxy-tetra-hydro-furan-2,5-dicarboxyl-ato-κO,O,O:O)(1,10-phenanthroline-κN,N')copper(II)] 0.69-hydrate].

In the crystal structure of the title compound, {[Cu(C(8)H(6)O(9))(C(12)H(8)N(2))]·0.69H(2)O}(n), the Cu(II) atom has a distorted octa-hedral geometry, coordinated by four O atoms from two 3,4-dicarboxy-tetra-hydro-furan-2,5-dicarboxyl-ate ligands and two N atoms from one 1,10-phenanthroline ligand. One of the carboxylate groups bridges the Cu(II) atoms, forming a zigzag chain running along the b axis. The chains are linked by a π-π inter-action between aromatic rings with a centroid-to-centroid distance of 3.567 (1) Å, and by hydrogen bonds between the carboxyl-ate group and the disordered water mol-ecule, forming a three-dimensional network.

Related literature

For related literature, see: Guillem et al. (1993 ▶).

Experimental

Crystal data

[Cu(C8H6O9)(C12H8N2)]·0.69H2O

M = 502.30

Monoclinic,

a = 12.9215 (7) Å

b = 8.5454 (5) Å

c = 17.597 (1) Å

β = 90.960 (3)°

V = 1942.85 (19) Å3

Z = 4

Mo Kα radiation

μ = 1.19 mm−1

T = 296 (2) K

0.20 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.797, T max = 0.910

24533 measured reflections

4444 independent reflections

3829 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.104

S = 1.06

4444 reflections

306 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.91 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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/S1600536808027918/is2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027918/is2325Isup2.hkl

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

[Cu(C8H6O9)(C12H8N2)]·0.69H2O	F(000) = 1023.6
Mr = 502.30	Dx = 1.717 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6566 reflections
a = 12.9215 (7) Å	θ = 2.6–27.5°
b = 8.5454 (5) Å	µ = 1.19 mm−1
c = 17.597 (1) Å	T = 296 K
β = 90.960 (3)°	Plate, blue
V = 1942.85 (19) Å3	0.20 × 0.16 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4444 independent reflections
Radiation source: fine-focus sealed tube	3829 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.797, Tmax = 0.910	k = −11→11
24533 measured reflections	l = −22→20

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.9393P] where P = (Fo2 + 2Fc2)/3
4444 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 0.91 e Å−3
3 restraints	Δρmin = −0.39 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)
Cu1	0.871218 (18)	0.24503 (2)	0.184653 (12)	0.02868 (10)
C1	1.01853 (16)	0.2951 (2)	0.30370 (12)	0.0349 (4)
C2	1.03192 (14)	0.1182 (2)	0.30175 (10)	0.0278 (4)
H2	1.1041	0.0927	0.2907	0.033*
C3	1.00314 (14)	0.0481 (2)	0.37973 (10)	0.0277 (4)
H3A	0.9546	0.1204	0.4036	0.033*
C4	1.09486 (16)	0.0275 (2)	0.43410 (11)	0.0345 (4)
C5	0.94334 (15)	−0.1007 (2)	0.35956 (11)	0.0295 (4)
H5	0.8924	−0.1258	0.3984	0.035*
C6	1.01493 (19)	−0.2386 (2)	0.34529 (14)	0.0381 (5)
C7	0.89004 (14)	−0.0507 (2)	0.28438 (10)	0.0270 (4)
H7	0.8764	−0.1442	0.2535	0.032*
C8	0.78735 (14)	0.0374 (2)	0.29592 (10)	0.0272 (4)
O1	0.95434 (13)	0.36239 (16)	0.26139 (9)	0.0423 (4)
O2	1.07474 (14)	0.36491 (17)	0.35212 (10)	0.0516 (4)
O3	1.15462 (14)	0.15169 (19)	0.44451 (10)	0.0527 (4)
H3	1.1322	0.2247	0.4189	0.063*
O4	1.11204 (13)	−0.09137 (19)	0.46799 (9)	0.0458 (4)
O5	1.0856 (2)	−0.2330 (2)	0.30242 (14)	0.0725 (7)
O6	0.98836 (14)	−0.36266 (18)	0.38404 (11)	0.0508 (4)
H6	1.0209	−0.4387	0.3690	0.061*
O7	0.77478 (11)	0.16687 (17)	0.26127 (8)	0.0361 (3)
O8	0.72265 (10)	−0.02515 (17)	0.33703 (8)	0.0343 (3)
O9	0.96504 (10)	0.04507 (15)	0.24653 (7)	0.0271 (3)
N1	0.80817 (13)	0.1145 (2)	0.09986 (9)	0.0353 (4)
N2	0.97214 (14)	0.2981 (2)	0.10238 (11)	0.0397 (4)
C9	0.72683 (18)	0.0188 (3)	0.10127 (15)	0.0476 (5)
H9	0.6918	0.0066	0.1466	0.057*
C10	0.6920 (2)	−0.0641 (3)	0.03716 (19)	0.0641 (8)
H10	0.6352	−0.1305	0.0405	0.077*
C11	0.7409 (3)	−0.0473 (3)	−0.02927 (18)	0.0666 (8)
H11	0.7177	−0.1016	−0.0721	0.080*
C12	0.8263 (2)	0.0516 (3)	−0.03391 (13)	0.0585 (8)
C13	0.8850 (3)	0.0778 (4)	−0.10042 (16)	0.0767 (10)
H13	0.8647	0.0298	−0.1457	0.092*
C14	0.9682 (3)	0.1693 (4)	−0.09929 (15)	0.0776 (12)
H14	1.0041	0.1835	−0.1441	0.093*
C15	1.0052 (3)	0.2479 (3)	−0.03111 (18)	0.0621 (9)
C16	1.0919 (3)	0.3406 (4)	−0.0257 (2)	0.0772 (11)
H16	1.1322	0.3564	−0.0684	0.093*
C17	1.1194 (2)	0.4099 (4)	0.0416 (2)	0.0764 (11)
H17	1.1789	0.4709	0.0452	0.092*
C18	1.05587 (19)	0.3877 (3)	0.10668 (18)	0.0587 (7)
H18	1.0735	0.4364	0.1523	0.070*
C19	0.9471 (2)	0.2285 (3)	0.03524 (13)	0.0436 (6)
C20	0.85840 (18)	0.1310 (3)	0.03349 (11)	0.0406 (5)
O10	0.2766 (4)	0.0628 (9)	0.2674 (5)	0.152 (2)	0.69
H10A	0.254 (7)	0.154 (5)	0.250 (6)	0.183*	0.69
H10B	0.252 (7)	−0.029 (4)	0.265 (6)	0.183*	0.69

	U11	U22	U33	U12	U13	U23
Cu1	0.03234 (15)	0.02857 (15)	0.02512 (15)	−0.00120 (8)	0.00022 (10)	0.00266 (8)
C1	0.0418 (11)	0.0240 (9)	0.0384 (10)	−0.0040 (8)	−0.0064 (9)	0.0026 (8)
C2	0.0296 (8)	0.0238 (8)	0.0300 (9)	−0.0004 (7)	−0.0021 (7)	−0.0006 (7)
C3	0.0336 (9)	0.0226 (8)	0.0270 (8)	0.0035 (7)	−0.0007 (7)	−0.0013 (7)
C4	0.0380 (10)	0.0323 (10)	0.0332 (10)	0.0039 (8)	−0.0037 (8)	0.0007 (8)
C5	0.0346 (9)	0.0239 (8)	0.0301 (9)	0.0016 (7)	0.0031 (7)	0.0020 (7)
C6	0.0474 (12)	0.0248 (10)	0.0420 (12)	0.0042 (8)	−0.0035 (10)	0.0000 (8)
C7	0.0331 (9)	0.0213 (8)	0.0267 (8)	−0.0034 (7)	0.0035 (7)	−0.0029 (6)
C8	0.0315 (9)	0.0275 (9)	0.0225 (8)	−0.0021 (7)	−0.0008 (7)	−0.0041 (7)
O1	0.0551 (9)	0.0250 (7)	0.0461 (8)	−0.0004 (6)	−0.0193 (7)	0.0028 (6)
O2	0.0656 (11)	0.0234 (7)	0.0646 (10)	−0.0047 (7)	−0.0331 (9)	0.0008 (7)
O3	0.0572 (10)	0.0370 (8)	0.0629 (10)	−0.0039 (7)	−0.0292 (8)	0.0070 (7)
O4	0.0514 (9)	0.0397 (8)	0.0459 (9)	0.0053 (7)	−0.0104 (7)	0.0108 (7)
O5	0.0888 (16)	0.0467 (11)	0.0834 (15)	0.0316 (10)	0.0424 (13)	0.0149 (9)
O6	0.0561 (10)	0.0223 (7)	0.0738 (12)	0.0018 (7)	−0.0037 (8)	0.0087 (7)
O7	0.0374 (7)	0.0350 (7)	0.0361 (7)	0.0080 (6)	0.0074 (6)	0.0078 (6)
O8	0.0347 (7)	0.0350 (7)	0.0334 (7)	−0.0061 (6)	0.0072 (6)	−0.0018 (6)
O9	0.0315 (6)	0.0257 (6)	0.0242 (6)	−0.0027 (5)	0.0033 (5)	−0.0019 (5)
N1	0.0404 (9)	0.0342 (9)	0.0311 (8)	0.0079 (7)	−0.0029 (7)	−0.0030 (7)
N2	0.0337 (9)	0.0369 (9)	0.0488 (10)	0.0056 (7)	0.0069 (8)	0.0160 (8)
C9	0.0450 (12)	0.0412 (12)	0.0563 (14)	0.0001 (10)	−0.0087 (10)	−0.0069 (11)
C10	0.0611 (16)	0.0495 (15)	0.081 (2)	0.0049 (12)	−0.0246 (15)	−0.0201 (14)
C11	0.081 (2)	0.0538 (16)	0.0642 (18)	0.0209 (15)	−0.0334 (16)	−0.0241 (14)
C12	0.0860 (19)	0.0555 (15)	0.0337 (11)	0.0405 (15)	−0.0073 (12)	−0.0057 (10)
C13	0.117 (3)	0.077 (2)	0.0367 (14)	0.039 (2)	0.0063 (16)	−0.0066 (14)
C14	0.122 (3)	0.077 (2)	0.0342 (13)	0.054 (2)	0.0328 (16)	0.0123 (14)
C15	0.0724 (19)	0.0581 (17)	0.0568 (16)	0.0342 (14)	0.0349 (15)	0.0264 (12)
C16	0.074 (2)	0.074 (2)	0.084 (2)	0.0359 (18)	0.0415 (18)	0.0384 (19)
C17	0.0376 (13)	0.0631 (18)	0.129 (3)	0.0090 (12)	0.0241 (16)	0.050 (2)
C18	0.0396 (12)	0.0516 (14)	0.0852 (19)	0.0005 (11)	0.0057 (12)	0.0284 (14)
C19	0.0554 (14)	0.0421 (12)	0.0337 (11)	0.0246 (10)	0.0138 (10)	0.0129 (9)
C20	0.0537 (12)	0.0383 (11)	0.0299 (10)	0.0203 (10)	−0.0003 (9)	0.0014 (8)
O10	0.075 (3)	0.173 (6)	0.211 (6)	0.005 (4)	0.054 (3)	0.054 (6)

Cu1—O7	1.9680 (14)	O6—H6	0.8200
Cu1—O1	1.9835 (15)	O8—Cu1ii	2.3363 (14)
Cu1—N2	2.0164 (18)	N1—C9	1.332 (3)
Cu1—N1	2.0235 (17)	N1—C20	1.353 (3)
Cu1—O8i	2.3363 (14)	N2—C18	1.326 (3)
Cu1—O9	2.3519 (13)	N2—C19	1.357 (3)
C1—O1	1.246 (2)	C9—C10	1.400 (4)
C1—O2	1.261 (3)	C9—H9	0.9300
C1—C2	1.522 (3)	C10—C11	1.346 (5)
C2—O9	1.433 (2)	C10—H10	0.9300
C2—C3	1.548 (2)	C11—C12	1.394 (5)
C2—H2	0.9800	C11—H11	0.9300
C3—C4	1.521 (3)	C12—C20	1.422 (3)
C3—C5	1.527 (3)	C12—C13	1.423 (4)
C3—H3A	0.9800	C13—C14	1.329 (5)
C4—O4	1.197 (3)	C13—H13	0.9300
C4—O3	1.323 (3)	C14—C15	1.449 (5)
C5—C6	1.521 (3)	C14—H14	0.9300
C5—C7	1.542 (3)	C15—C16	1.374 (5)
C5—H5	0.9800	C15—C19	1.408 (3)
C6—O5	1.195 (3)	C16—C17	1.367 (5)
C6—O6	1.309 (3)	C16—H16	0.9300
C7—O9	1.440 (2)	C17—C18	1.433 (4)
C7—C8	1.542 (3)	C17—H17	0.9300
C7—H7	0.9800	C18—H18	0.9300
C8—O8	1.236 (2)	C19—C20	1.417 (4)
C8—O7	1.272 (2)	O10—H10A	0.89 (2)
O3—H3	0.8200	O10—H10B	0.85 (2)
O7—Cu1—O1	92.69 (7)	C1—O1—Cu1	121.38 (13)
O7—Cu1—N2	173.13 (7)	C4—O3—H3	109.5
O1—Cu1—N2	91.47 (8)	C6—O6—H6	109.5
O7—Cu1—N1	93.81 (7)	C8—O7—Cu1	123.11 (12)
O1—Cu1—N1	170.96 (7)	C8—O8—Cu1ii	128.49 (12)
N2—Cu1—N1	81.48 (8)	C2—O9—C7	109.69 (13)
O7—Cu1—O8i	93.68 (5)	C2—O9—Cu1	107.31 (10)
O1—Cu1—O8i	87.70 (6)	C7—O9—Cu1	106.35 (10)
N2—Cu1—O8i	91.94 (6)	C9—N1—C20	118.0 (2)
N1—Cu1—O8i	98.13 (6)	C9—N1—Cu1	129.25 (16)
O7—Cu1—O9	76.32 (5)	C20—N1—Cu1	112.71 (15)
O1—Cu1—O9	77.47 (5)	C18—N2—C19	119.0 (2)
N2—Cu1—O9	99.28 (6)	C18—N2—Cu1	128.7 (2)
N1—Cu1—O9	97.98 (6)	C19—N2—Cu1	112.27 (16)
O8i—Cu1—O9	161.54 (5)	N1—C9—C10	122.6 (3)
O1—C1—O2	123.73 (19)	N1—C9—H9	118.7
O1—C1—C2	121.33 (18)	C10—C9—H9	118.7
O2—C1—C2	114.90 (17)	C11—C10—C9	119.8 (3)
O9—C2—C1	112.38 (15)	C11—C10—H10	120.1
O9—C2—C3	106.34 (14)	C9—C10—H10	120.1
C1—C2—C3	109.59 (15)	C10—C11—C12	120.0 (2)
O9—C2—H2	109.5	C10—C11—H11	120.0
C1—C2—H2	109.5	C12—C11—H11	120.0
C3—C2—H2	109.5	C11—C12—C20	117.4 (3)
C4—C3—C5	115.85 (15)	C11—C12—C13	125.3 (3)
C4—C3—C2	113.96 (16)	C20—C12—C13	117.3 (3)
C5—C3—C2	104.14 (14)	C14—C13—C12	121.5 (3)
C4—C3—H3A	107.5	C14—C13—H13	119.3
C5—C3—H3A	107.5	C12—C13—H13	119.3
C2—C3—H3A	107.5	C13—C14—C15	122.7 (3)
O4—C4—O3	120.58 (19)	C13—C14—H14	118.6
O4—C4—C3	123.20 (19)	C15—C14—H14	118.6
O3—C4—C3	116.18 (17)	C16—C15—C19	117.1 (3)
C6—C5—C3	112.12 (16)	C16—C15—C14	125.6 (3)
C6—C5—C7	109.70 (16)	C19—C15—C14	117.3 (3)
C3—C5—C7	100.71 (14)	C17—C16—C15	120.6 (3)
C6—C5—H5	111.3	C17—C16—H16	119.7
C3—C5—H5	111.3	C15—C16—H16	119.7
C7—C5—H5	111.3	C16—C17—C18	119.4 (3)
O5—C6—O6	124.8 (2)	C16—C17—H17	120.3
O5—C6—C5	123.10 (19)	C18—C17—H17	120.3
O6—C6—C5	112.1 (2)	N2—C18—C17	120.6 (3)
O9—C7—C5	105.07 (14)	N2—C18—H18	119.7
O9—C7—C8	111.73 (14)	C17—C18—H18	119.7
C5—C7—C8	113.30 (14)	N2—C19—C15	123.2 (3)
O9—C7—H7	108.9	N2—C19—C20	117.23 (19)
C5—C7—H7	108.9	C15—C19—C20	119.6 (3)
C8—C7—H7	108.9	N1—C20—C19	116.2 (2)
O8—C8—O7	125.07 (18)	N1—C20—C12	122.2 (2)
O8—C8—C7	117.21 (16)	C19—C20—C12	121.5 (2)
O7—C8—C7	117.70 (15)	H10A—O10—H10B	133 (6)
O1—C1—C2—O9	0.9 (3)	N1—Cu1—O9—C7	−73.04 (11)
O2—C1—C2—O9	179.11 (18)	O8i—Cu1—O9—C7	77.61 (18)
O1—C1—C2—C3	−117.1 (2)	O7—Cu1—N1—C9	2.64 (19)
O2—C1—C2—C3	61.1 (2)	O1—Cu1—N1—C9	138.5 (4)
O9—C2—C3—C4	144.82 (15)	N2—Cu1—N1—C9	177.6 (2)
C1—C2—C3—C4	−93.47 (19)	O8i—Cu1—N1—C9	−91.63 (19)
O9—C2—C3—C5	17.66 (18)	O9—Cu1—N1—C9	79.35 (19)
C1—C2—C3—C5	139.37 (16)	O7—Cu1—N1—C20	−177.48 (14)
C5—C3—C4—O4	−10.3 (3)	O1—Cu1—N1—C20	−41.6 (5)
C2—C3—C4—O4	−131.1 (2)	N2—Cu1—N1—C20	−2.51 (14)
C5—C3—C4—O3	171.93 (18)	O8i—Cu1—N1—C20	88.24 (14)
C2—C3—C4—O3	51.1 (2)	O9—Cu1—N1—C20	−100.77 (14)
C4—C3—C5—C6	−42.0 (2)	O7—Cu1—N2—C18	−130.7 (5)
C2—C3—C5—C6	83.97 (19)	O1—Cu1—N2—C18	−3.3 (2)
C4—C3—C5—C7	−158.57 (16)	N1—Cu1—N2—C18	−177.7 (2)
C2—C3—C5—C7	−32.60 (17)	O8i—Cu1—N2—C18	84.4 (2)
C3—C5—C6—O5	−51.7 (3)	O9—Cu1—N2—C18	−80.9 (2)
C7—C5—C6—O5	59.3 (3)	O7—Cu1—N2—C19	48.8 (6)
C3—C5—C6—O6	129.65 (19)	O1—Cu1—N2—C19	176.18 (14)
C7—C5—C6—O6	−119.3 (2)	N1—Cu1—N2—C19	1.86 (14)
C6—C5—C7—O9	−81.17 (18)	O8i—Cu1—N2—C19	−96.07 (14)
C3—C5—C7—O9	37.17 (17)	O9—Cu1—N2—C19	98.63 (14)
C6—C5—C7—C8	156.60 (16)	C20—N1—C9—C10	−0.1 (3)
C3—C5—C7—C8	−85.06 (17)	Cu1—N1—C9—C10	179.79 (18)
O9—C7—C8—O8	−170.15 (15)	N1—C9—C10—C11	−0.5 (4)
C5—C7—C8—O8	−51.7 (2)	C9—C10—C11—C12	0.4 (4)
O9—C7—C8—O7	11.3 (2)	C10—C11—C12—C20	0.3 (4)
C5—C7—C8—O7	129.76 (17)	C10—C11—C12—C13	179.3 (3)
O2—C1—O1—Cu1	178.38 (18)	C11—C12—C13—C14	−177.2 (3)
C2—C1—O1—Cu1	−3.6 (3)	C20—C12—C13—C14	1.8 (4)
O7—Cu1—O1—C1	78.65 (18)	C12—C13—C14—C15	0.2 (5)
N2—Cu1—O1—C1	−95.88 (18)	C13—C14—C15—C16	178.3 (3)
N1—Cu1—O1—C1	−57.3 (5)	C13—C14—C15—C19	−2.2 (4)
O8i—Cu1—O1—C1	172.23 (18)	C19—C15—C16—C17	0.1 (4)
O9—Cu1—O1—C1	3.30 (17)	C14—C15—C16—C17	179.7 (3)
O8—C8—O7—Cu1	−170.39 (14)	C15—C16—C17—C18	−1.2 (4)
C7—C8—O7—Cu1	8.0 (2)	C19—N2—C18—C17	−0.4 (3)
O1—Cu1—O7—C8	−91.67 (15)	Cu1—N2—C18—C17	179.09 (18)
N2—Cu1—O7—C8	35.6 (6)	C16—C17—C18—N2	1.4 (4)
N1—Cu1—O7—C8	82.04 (15)	C18—N2—C19—C15	−0.8 (3)
O8i—Cu1—O7—C8	−179.54 (15)	Cu1—N2—C19—C15	179.66 (17)
O9—Cu1—O7—C8	−15.26 (14)	C18—N2—C19—C20	178.61 (19)
O7—C8—O8—Cu1ii	111.36 (19)	Cu1—N2—C19—C20	−1.0 (2)
C7—C8—O8—Cu1ii	−67.1 (2)	C16—C15—C19—N2	0.9 (3)
C1—C2—O9—C7	−113.58 (17)	C14—C15—C19—N2	−178.7 (2)
C3—C2—O9—C7	6.33 (18)	C16—C15—C19—C20	−178.5 (2)
C1—C2—O9—Cu1	1.55 (17)	C14—C15—C19—C20	2.0 (3)
C3—C2—O9—Cu1	121.46 (11)	C9—N1—C20—C19	−177.37 (19)
C5—C7—O9—C2	−27.77 (17)	Cu1—N1—C20—C19	2.7 (2)
C8—C7—O9—C2	95.47 (16)	C9—N1—C20—C12	0.8 (3)
C5—C7—O9—Cu1	−143.52 (11)	Cu1—N1—C20—C12	−179.11 (16)
C8—C7—O9—Cu1	−20.27 (15)	N2—C19—C20—N1	−1.2 (3)
O7—Cu1—O9—C2	−98.38 (11)	C15—C19—C20—N1	178.19 (19)
O1—Cu1—O9—C2	−2.43 (11)	N2—C19—C20—C12	−179.37 (19)
N2—Cu1—O9—C2	87.02 (12)	C15—C19—C20—C12	0.0 (3)
N1—Cu1—O9—C2	169.62 (11)	C11—C12—C20—N1	−0.9 (3)
O8i—Cu1—O9—C2	−39.7 (2)	C13—C12—C20—N1	180.0 (2)
O7—Cu1—O9—C7	18.96 (10)	C11—C12—C20—C19	177.2 (2)
O1—Cu1—O9—C7	114.90 (11)	C13—C12—C20—C19	−2.0 (3)
N2—Cu1—O9—C7	−155.65 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O5i	0.89 (2)	2.47 (10)	2.793 (6)	102 (7)
O6—H6···O2iii	0.82	1.84	2.646 (2)	166.
O3—H3···O2	0.82	1.83	2.641 (2)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10A⋯O5i	0.89 (2)	2.47 (10)	2.793 (6)	102 (7)
O6—H6⋯O2ii	0.82	1.84	2.646 (2)	166
O3—H3⋯O2	0.82	1.83	2.641 (2)	172

Symmetry codes: (i) ; (ii) .