Poly[bis­([mu]₃-5'-carb­oxy-2,2'-bipyridine-5-carboxyl­ato-[kappa]⁴O:N,N':O')lead(II)]

The title compound, [Pb(C₁₂H₇N₂O₄)₂]_n, obtained by reaction of Pb(NO₃)₂ and 2,2'-bipyridine-5,5'-dicarboxylic acid (H₂bptc) under hydro­thermal conditions, has a structure in which the unique Pb^II cation sits on a twofold axis and is octa-coordinated by four O-atom donors from four Hbptc^- ligands and four N-atom donors from two Hbptc^- ligands in a distorted dodeca­hedral geometry. With each Pb^II cation connected to six Hbptc^- ligands and each Hbptc^- ligand bridging three Pb^II cations, a three-dimensional polymeric structure is formed. From a topological point of view, the three-dimensional net is binodal, with six-connected (the Pb^II cation) and three-connected (the Hbptc^- ligand) nodes, resulting in a distorted rutile (4².8)₂(4⁴8⁹12²) topology.

S1. Comment

The design and synthesis of high-dimensional metal–organic framework (MOF) structures is becoming an increasingly popular field of research due to their formation of interesting structures and their potentially useful ion-exchange, adsorption, catalytic, fluorescence and magnetic properties (Leininger et al., 2000; Seo et al., 2000; Swiegers & Malefetse, 2000; Wu et al., 2005; Spencer et al., 2006). The construction of coordination networks with different topological structures has attracted significant attention from chemists (Barbour, 2001). Consequently, a variety of three-dimensional MOFs have been prepared by taking certain factors into account, such as the coordination nature of the metal ion and the shape, functionality, flexibility and symmetry of the organic ligand (Reger et al., 2001; Kitaura et al., 2002, 2003). The key step in forming infinite structures with particular architectures is to select appropriate bridging ligands, with rigid multidentate ligands being particularly advantageous. Ligands derived from 2,2'-bipyridine-5,5'-dicarboxylic acid (H₂bptc) are effective in this regard in that they contain a number of N- and O-coordination sites and rich coordination modes. They have shown not only strong chelating ability, but also a bridging tendency, yielding mono- or polynuclear one-, two- or three-dimensional structures, depending on the metal ion and the coligand used (Desmartin et al., 1995; Finn & Zubieta 2000; Min et al., 2002; Tynan et al., 2003; Lee & Suh, 2004; Matthews et al., 2004; Schoknecht & Kempe, 2004; Szeto et al., 2006, 2008). Among the reported structures, only one containing neodymium is three-dimensional (Schoknecht & Kempe, 2004). The greater dimensionality can be attributed to the high coordination numbers of lanthanides, which provide more opportunities to extend in different directions. Furthermore, the published metal compounds are limited to transition and lanthanide metals, while complexes with main group metals are still absent.

The hydrothermal method has been a promising technique in preparing highly stable infinite metal–ligand frameworks (Yaghi & Li, 1995; Gutschke et al., 1996; Chui et al., 1996; Gerrard & Wood, 2000). Taking advantage of the bridging ability of H₂bptc in the chemical design of metal–organic molecular assemblies and the potentially high coordination number of Pb^II, we have synthesized the title novel three-dimensional coordination polymer, (I), under hydrothermal conditions.

Compound (I) represents a rare example of a three-dimensional framework with three- and six-connected nodes which exhibits a rutile-related (4².8)₂(4⁴ 8⁹ 12²) topology. The structure of (I) is distinctly different from the three-dimensional structure of the previously reported neodymium complex [Nd₂(bpdc)₃(H₂O)₄]_n, in which the lanthanide centres act as five-connectors and two types of ligand cross-linkers as three- and four-connectors (Schoknecht & Kempe, 2004).

The asymmetric unit of (I) contains one-half of a Pb^II cation, located on a two-fold rotation axis, and an Hbptc^- anion (Fig. 1). Thus, the carboxyl groups of H₂bptc are partly deprotonated to produce Hbptc^-, which is in agreement with the IR data in which strong absorption peaks were observed around 1700 cm^-1 for -COOH. Each Pb^II cation has a distorted dodecahedral coordination environment with four N atoms from two chelating Hbptc^- anions (N1, N2, N1^iv and N2^iv; all symmetry codes as in Fig. 1) and four O atoms from four other Hbptc^- anions (O2^v, O2ⁱⁱ, O4ⁱ and O4ⁱⁱⁱ). In total, each Pb^II cation is connected to six Hbptc^- ligands, defining a six-connected node within the structure. The C—O distances (Table 1) are close to each other and fall between the extremes of C—O single bonds (ca 1.32 Å) and C═O double bonds (ca 1.21 Å) typically observed in carboxyl groups (Zhang et al., 2005). The C—O distances involving non-coordinated O atoms are slightly longer than those involving coordinated O atoms. Obvious peaks adjacent to atoms O3 and O1 can be seen in the difference electron-density maps. All these observations suggest that the H atom is actually disordered between the non-coordinated O atoms. The Hbptc^- anion coordinates to three Pb^II centres, to Pb1 in a bidentate chelating mode and to Pb1^v and Pb1^vi in a monodentate bridging mode. Thus, each Hbptc^- ligand affords a three-connected node.

Each mononuclear Pb unit is linked to eight neighbouring mononuclear units to form a three-dimensional framework through the Hbptc^- ligands. Four neighbouring Pb^II cations are linked at two different distances through C₅H₃NCOO^- spacers (half of the Hbptc^- ligand) [Pb1–Pb1^v = 7.83990 (6) Å and Pb1–Pb1^vi = 9.4850 (8) Å], while four other Pb^II cations are linked through ^-OOC(C₅H₃N)₂COOH spacers (the whole Hbptc^- ligand) [Pb1–Pb1^vii = 15.4712 (14)Å]. The connecting mode of the mononuclear units within the ac and bc planes are shown in Figs. 2 and 3, respectively.

A better insight into the nature of this intricate framework can be achieved by the application of a topological approach, i.e. reducing multidimensional structures to simple node and connection nets. As discussed above, the structure of (I) is binodal with six- (Pb^II) and three-connected (Hbptc^-) nodes. The framework can be rationalized by considering the shortest circuits starting and ending at Pb^II and Hbptc^-, leading to the formation of a distorted rutile (4².8)₂(4⁴ 8⁹ 12²) topology (Fig. 4) (Blatov et al., 2005).

S2. Experimental

A mixture of Pb(NO₃)₂ (0.2 mmol, 66 mg), H₂bptc (0.4 mmol, 98 mg) and H₂O (18.0 ml) in a molar ratio of 1:2:5000 was sealed in a 25 ml stainless steel reactor with a Teflon liner. The reactor was directly heated to 453 K, held at that temperature for 72 h and then slowly cooled to 303 K at a rate of 4 K h^-1. Green block crystals of the title complex were collected by filtration and washed with ethanol (yield 35%).

S3. Refinement

Although evidence of possible disorder was found in the difference electron-density map, carboxyl atom H3 on O3 was included at full occupancy and treated as a riding atom, with O—H = 0.82 Å. The aromatic H atoms were placed at calculated positions, with C—H = 0.93 Å. All H atoms were assigned fixed isotropic displacement parameters, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. A view of the local coordination of the Pb^II cations in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for the sake of clarity. [Symmetry codes: (i) x - 1/2, y - 1/2, z; (ii) -x + 3/2, -y - 1/2, -z; (iii) x + 1/2, -y - 1/2, z + 1/2; (iv) -x + 5/2, y - 1/2, -z + 1/2; (v) -x + 2, y, -z + 1/2, z; (vi) x + 1/2, y + 1/2.]
	Fig. 2. The packing of (I), viewed along the b axis, showing the connection mode of the mononuclear units within the ac plane.
	Fig. 3. The packing of (I), viewed along the a axis, showing the connection mode of the mononuclear units within the bc plane.
	Fig. 4. A schematic representation of the distorted rutile (4^2.8)2(4^4 8^9 12^2) topology of (I). Pb^II cations are shown as large spheres and Hbptc^- anions as small spheres.

Poly[bis(µ₃-5'-carboxy-2,2'-bipyridine-5-carboxylato- κ⁴O:N,N':O')lead(II)]

Crystal data

[Pb(C12H7N2O4)2]	F(000) = 1328
Mr = 693.58	Dx = 2.183 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 5931 reflections
a = 15.1836 (17) Å	θ = 2.3–28.2°
b = 11.3719 (13) Å	µ = 8.06 mm^−1
c = 13.5342 (16) Å	T = 291 K
β = 115.447 (1)°	Block, green
V = 2110.2 (4) Å^3	0.20 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1977 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ϕ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.296, Tmax = 0.565	k = −13→13
7034 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.049	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0284P)^2 + 3.5386P] where P = (Fo^2 + 2Fc^2)/3
1977 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −1.44 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pb1	1.0000	−0.185023 (14)	0.2500	0.02158 (8)
O1	1.35482 (18)	0.0450 (3)	0.3027 (3)	0.0431 (7)
O2	1.33990 (19)	0.2374 (3)	0.2601 (3)	0.0427 (7)
O3	0.53033 (17)	0.0145 (2)	−0.1189 (3)	0.0393 (7)
H3	0.4765	−0.0169	−0.1437	0.059*
O4	0.5826 (2)	−0.1696 (2)	−0.0702 (3)	0.0365 (7)
N1	1.05914 (19)	−0.0069 (2)	0.1651 (2)	0.0234 (6)
N2	0.86879 (19)	−0.0556 (3)	0.0862 (2)	0.0242 (6)
C1	1.1553 (2)	0.0136 (3)	0.2098 (3)	0.0228 (7)
H1	1.1972	−0.0493	0.2416	0.027*
C2	1.1966 (2)	0.1240 (3)	0.2116 (3)	0.0214 (7)
C3	1.1322 (3)	0.2174 (3)	0.1641 (3)	0.0302 (8)
H3A	1.1560	0.2932	0.1663	0.036*
C4	1.0322 (3)	0.1960 (3)	0.1134 (4)	0.0305 (9)
H4	0.9887	0.2567	0.0792	0.037*
C5	0.9984 (2)	0.0825 (3)	0.1147 (3)	0.0212 (7)
C6	0.8921 (2)	0.0515 (3)	0.0612 (3)	0.0210 (7)
C7	0.8212 (2)	0.1262 (3)	−0.0118 (3)	0.0278 (8)
H7	0.8387	0.1984	−0.0302	0.033*
C8	0.7239 (2)	0.0916 (3)	−0.0568 (3)	0.0283 (8)
H8	0.6755	0.1413	−0.1042	0.034*
C9	0.6999 (2)	−0.0179 (3)	−0.0302 (3)	0.0231 (7)
C10	0.7750 (2)	−0.0891 (3)	0.0406 (3)	0.0243 (7)
H10	0.7595	−0.1634	0.0570	0.029*
C11	1.3063 (2)	0.1379 (3)	0.2624 (3)	0.0245 (7)
C12	0.5974 (2)	−0.0649 (3)	−0.0754 (3)	0.0255 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00992 (10)	0.01709 (11)	0.03104 (12)	0.000	0.00243 (8)	0.000
O1	0.0101 (12)	0.0383 (16)	0.067 (2)	−0.0024 (11)	0.0033 (12)	0.0076 (14)
O2	0.0171 (13)	0.0330 (15)	0.073 (2)	−0.0090 (12)	0.0150 (14)	0.0014 (15)
O3	0.0077 (11)	0.0340 (15)	0.0625 (19)	0.0009 (10)	0.0020 (12)	0.0034 (13)
O4	0.0167 (14)	0.0309 (15)	0.0467 (17)	−0.0045 (10)	−0.0007 (12)	−0.0030 (12)
N1	0.0099 (13)	0.0238 (14)	0.0317 (16)	−0.0010 (11)	0.0044 (12)	0.0013 (12)
N2	0.0100 (12)	0.0257 (15)	0.0300 (15)	−0.0010 (11)	0.0020 (11)	0.0008 (13)
C1	0.0115 (15)	0.0244 (17)	0.0286 (18)	0.0035 (13)	0.0049 (13)	0.0024 (14)
C2	0.0102 (15)	0.0261 (17)	0.0273 (18)	−0.0031 (13)	0.0074 (13)	−0.0029 (14)
C3	0.0174 (18)	0.0233 (17)	0.045 (2)	−0.0038 (14)	0.0094 (17)	0.0029 (16)
C4	0.0144 (18)	0.0255 (19)	0.046 (2)	0.0028 (13)	0.0074 (17)	0.0064 (15)
C5	0.0116 (15)	0.0229 (17)	0.0274 (17)	0.0000 (12)	0.0066 (13)	0.0005 (14)
C6	0.0113 (15)	0.0238 (17)	0.0257 (17)	0.0012 (13)	0.0057 (13)	−0.0017 (14)
C7	0.0146 (16)	0.0289 (19)	0.034 (2)	−0.0004 (14)	0.0050 (15)	0.0061 (16)
C8	0.0140 (16)	0.0296 (19)	0.0335 (19)	0.0063 (14)	0.0029 (14)	0.0046 (15)
C9	0.0109 (15)	0.0292 (18)	0.0255 (18)	−0.0001 (13)	0.0041 (13)	−0.0052 (14)
C10	0.0142 (16)	0.0232 (17)	0.0309 (19)	−0.0025 (13)	0.0055 (14)	−0.0013 (14)
C11	0.0128 (16)	0.0305 (19)	0.0275 (18)	−0.0013 (14)	0.0062 (14)	−0.0028 (15)
C12	0.0140 (16)	0.0288 (19)	0.0278 (17)	0.0006 (14)	0.0031 (13)	−0.0033 (15)

Geometric parameters (Å, º)

Pb1—O2^i	2.644 (3)	N2—C6	1.351 (4)
Pb1—O2^ii	2.644 (3)	C1—C2	1.398 (5)
Pb1—N1^iii	2.667 (3)	C1—H1	0.9300
Pb1—N1	2.667 (3)	C2—C3	1.399 (5)
Pb1—N2^iii	2.694 (3)	C2—C11	1.513 (4)
Pb1—N2	2.694 (3)	C3—C4	1.392 (5)
Pb1—O4^iv	2.758 (3)	C3—H3A	0.9300
Pb1—O4^v	2.758 (3)	C4—C5	1.392 (5)
O1—C11	1.269 (5)	C4—H4	0.9300
O2—C11	1.247 (5)	C5—C6	1.500 (4)
O2—Pb1^vi	2.644 (3)	C6—C7	1.394 (5)
O3—C12	1.298 (4)	C7—C8	1.391 (5)
O3—H3	0.8200	C7—H7	0.9300
O4—C12	1.219 (4)	C8—C9	1.387 (5)
O4—Pb1^iv	2.758 (3)	C8—H8	0.9300
N1—C1	1.339 (4)	C9—C10	1.391 (5)
N1—C5	1.345 (4)	C9—C12	1.505 (4)
N2—C10	1.341 (4)	C10—H10	0.9300
O2^i—Pb1—O2^ii	141.03 (13)	N1—C1—C2	123.8 (3)
O2^i—Pb1—N1^iii	75.17 (9)	N1—C1—H1	118.1
O2^ii—Pb1—N1^iii	139.69 (9)	C2—C1—H1	118.1
O2^i—Pb1—N1	139.69 (9)	C1—C2—C3	117.0 (3)
O2^ii—Pb1—N1	75.17 (9)	C1—C2—C11	119.9 (3)
N1^iii—Pb1—N1	81.17 (12)	C3—C2—C11	123.0 (3)
O2^i—Pb1—N2^iii	120.73 (10)	C4—C3—C2	119.5 (3)
O2^ii—Pb1—N2^iii	81.58 (9)	C4—C3—H3A	120.3
N1^iii—Pb1—N2^iii	59.82 (8)	C2—C3—H3A	120.3
N1—Pb1—N2^iii	70.89 (9)	C5—C4—C3	119.1 (3)
O2^i—Pb1—N2	81.58 (9)	C5—C4—H4	120.5
O2^ii—Pb1—N2	120.73 (10)	C3—C4—H4	120.5
N1^iii—Pb1—N2	70.89 (9)	N1—C5—C4	122.1 (3)
N1—Pb1—N2	59.82 (8)	N1—C5—C6	115.4 (3)
N2^iii—Pb1—N2	113.75 (12)	C4—C5—C6	122.5 (3)
O2^i—Pb1—O4^iv	76.46 (10)	N2—C6—C7	121.4 (3)
O2^ii—Pb1—O4^iv	80.46 (9)	N2—C6—C5	115.7 (3)
N1^iii—Pb1—O4^iv	136.50 (8)	C7—C6—C5	122.8 (3)
N1—Pb1—O4^iv	100.65 (9)	C8—C7—C6	119.3 (3)
N2^iii—Pb1—O4^iv	161.64 (9)	C8—C7—H7	120.3
N2—Pb1—O4^iv	72.90 (9)	C6—C7—H7	120.3
O2^i—Pb1—O4^v	80.46 (9)	C9—C8—C7	119.2 (3)
O2^ii—Pb1—O4^v	76.46 (10)	C9—C8—H8	120.4
N1^iii—Pb1—O4^v	100.65 (9)	C7—C8—H8	120.4
N1—Pb1—O4^v	136.50 (8)	C8—C9—C10	118.2 (3)
N2^iii—Pb1—O4^v	72.90 (9)	C8—C9—C12	123.7 (3)
N2—Pb1—O4^v	161.64 (9)	C10—C9—C12	118.1 (3)
O4^iv—Pb1—O4^v	106.36 (12)	N2—C10—C9	123.0 (3)
C11—O2—Pb1^vi	134.3 (2)	N2—C10—H10	118.5
C12—O3—H3	109.5	C9—C10—H10	118.5
C12—O4—Pb1^iv	124.0 (3)	O2—C11—O1	126.7 (3)
C1—N1—C5	118.4 (3)	O2—C11—C2	117.8 (3)
C1—N1—Pb1	116.2 (2)	O1—C11—C2	115.5 (3)
C5—N1—Pb1	120.5 (2)	O4—C12—O3	125.3 (3)
C10—N2—C6	118.8 (3)	O4—C12—C9	120.5 (3)
C10—N2—Pb1	119.1 (2)	O3—C12—C9	114.2 (3)
C6—N2—Pb1	121.2 (2)
O2^i—Pb1—N1—C1	160.3 (2)	C1—N1—C5—C4	−3.9 (5)
O2^ii—Pb1—N1—C1	−41.1 (2)	Pb1—N1—C5—C4	150.3 (3)
N1^iii—Pb1—N1—C1	106.0 (3)	C1—N1—C5—C6	176.7 (3)
N2^iii—Pb1—N1—C1	45.0 (2)	Pb1—N1—C5—C6	−29.1 (4)
N2—Pb1—N1—C1	179.0 (3)	C3—C4—C5—N1	1.3 (6)
O4^iv—Pb1—N1—C1	−118.1 (2)	C3—C4—C5—C6	−179.3 (4)
O4^v—Pb1—N1—C1	9.8 (3)	C10—N2—C6—C7	−1.0 (5)
O2^i—Pb1—N1—C5	5.6 (3)	Pb1—N2—C6—C7	−170.2 (3)
O2^ii—Pb1—N1—C5	164.2 (3)	C10—N2—C6—C5	−179.6 (3)
N1^iii—Pb1—N1—C5	−48.7 (2)	Pb1—N2—C6—C5	11.2 (4)
N2^iii—Pb1—N1—C5	−109.7 (3)	N1—C5—C6—N2	11.3 (4)
N2—Pb1—N1—C5	24.3 (2)	C4—C5—C6—N2	−168.1 (3)
O4^iv—Pb1—N1—C5	87.2 (3)	N1—C5—C6—C7	−167.2 (3)
O4^v—Pb1—N1—C5	−144.9 (2)	C4—C5—C6—C7	13.4 (5)
O2^i—Pb1—N2—C10	−18.9 (3)	N2—C6—C7—C8	2.4 (5)
O2^ii—Pb1—N2—C10	126.9 (2)	C5—C6—C7—C8	−179.1 (3)
N1^iii—Pb1—N2—C10	−96.0 (3)	C6—C7—C8—C9	−1.7 (6)
N1—Pb1—N2—C10	173.2 (3)	C7—C8—C9—C10	−0.3 (5)
N2^iii—Pb1—N2—C10	−138.8 (3)	C7—C8—C9—C12	−179.1 (3)
O4^iv—Pb1—N2—C10	59.5 (3)	C6—N2—C10—C9	−1.1 (5)
O4^v—Pb1—N2—C10	−31.0 (4)	Pb1—N2—C10—C9	168.3 (3)
O2^i—Pb1—N2—C6	150.3 (3)	C8—C9—C10—N2	1.7 (5)
O2^ii—Pb1—N2—C6	−64.0 (3)	C12—C9—C10—N2	−179.4 (3)
N1^iii—Pb1—N2—C6	73.1 (2)	Pb1^vi—O2—C11—O1	30.4 (6)
N1—Pb1—N2—C6	−17.6 (2)	Pb1^vi—O2—C11—C2	−149.1 (3)
N2^iii—Pb1—N2—C6	30.3 (2)	C1—C2—C11—O2	178.5 (3)
O4^iv—Pb1—N2—C6	−131.4 (3)	C3—C2—C11—O2	−0.9 (5)
O4^v—Pb1—N2—C6	138.1 (3)	C1—C2—C11—O1	−1.0 (5)
C5—N1—C1—C2	3.0 (5)	C3—C2—C11—O1	179.6 (4)
Pb1—N1—C1—C2	−152.3 (3)	Pb1^iv—O4—C12—O3	65.8 (5)
N1—C1—C2—C3	0.5 (5)	Pb1^iv—O4—C12—C9	−113.6 (3)
N1—C1—C2—C11	−179.0 (3)	C8—C9—C12—O4	162.9 (4)
C1—C2—C3—C4	−3.1 (6)	C10—C9—C12—O4	−15.9 (5)
C11—C2—C3—C4	176.3 (4)	C8—C9—C12—O3	−16.6 (5)
C2—C3—C4—C5	2.3 (6)	C10—C9—C12—O3	164.6 (3)

Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x+5/2, y−1/2, −z+1/2; (iii) −x+2, y, −z+1/2; (iv) −x+3/2, −y−1/2, −z; (v) x+1/2, −y−1/2, z+1/2; (vi) x+1/2, y+1/2, z.