2-(exo-Tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-endo-yl)acetaldehyde 2,4-dinitrophenylhydrazone

The six-membered ring of the norbornene moiety in the title compound, C₁₈H₁₈N₄O₄, is in a slightly distorted boat conformation, and the two five-membered rings within it adopt envelope conformations. The structure is stabilized by inter- and intramolecular N—H...O hydrogen bonds.

S1. Comment

It is known that norbornene derivatives, besides being biologically active by themselves, are used in the synthesis of other compounds possessing psychotropic, anticonvulsant and antimicrobial activities (Minoru, Morio & Hiroyuki, 1974; Minoru, Morio, Hiroyuki & Yasuo, 1974; Tasihiko & Syundzi, 1971). Norbornene derivatives are also used as efficient turn elements in the design of simple models of two-stranded parallel β sheets and hairpin cyclic peptides (Ranganathan et al., 1998, 2000). In view of these features associated with the norbornene moiety, the present structure determination of the title compound, (III), was undertaken. \sch

Another reason for undertaking a crystallographic study of (III) was to establish the configuration of the acetaldehyde chain in the rearrangement product, (II) (Scheme), since this was difficult to define from the ¹H NMR spectrum. In all the available literature, the γ C atom of the vinyl ether is disubstituted, so that one can easily find out whether the product of the rearrangement of the allyl vinyl ether moiety is due to a formal 1,3 or 3,3 shift of its structure. But in the case of (II) (Palani et al., 1998), since the γ C atom is not disubstituted and the starting material was racemic, it is difficult to find out whether the product is due to a 3,3 or a 1,3 shift. In order to estabilish the configuration of the acetaldehyde chain, the aldehyde was converted into its 2,4-dinitrophenylhydrazone derivative, the title compound, (III) (Fig. 1). The present X-ray crystal structure analysis showed that the acetaldehyde chain is in the α position.

The bond lengths and angles in (III) agree with the normal values (Allen et al., 1987). In particular, the bond lengths and angles of the norbornene moiety agree with the values in the literature (Milovac et al., 2001; Beddoes et al., 1993; Dvorkin et al., 1987). The six-membered ring, C1/C2/C6—C9, is in a slightly distorted boat conformation with two local pseudo mirrors, one along the mid-points of the C2—C6 and C8—C9 bonds, and the other along the C1—C7 direction. The ring puckering (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) for this ring, calculated using PARST97 (Nardelli, 1995), are Q_T = 0.951 (4) Å, ΔC_s(C1) = 0.016 (2)° and ΔC_s(C6—C2) = 0.008 (2)°. The C1/C2/C6/C7/C10 and C1/C9/C8/C7/C10 rings are both in an envelope conformation, with a pseudo mirror running through atom C10. The total puckering amplitute and asymmetry parameter for the C1/C2/C6/C7/C10 ring are q₂ = 0.602 (4) Å and ΔC_s(C10) = 0.012 (2)°, respectively, and the corresponding values for the C1/C9/C8/C7/C10 ring are q₂ = 0.554 (4) Å and ΔC_s(C10) = 0.008 (2)°, respectively.

The five-membered ring C is planar. The two nitro groups are nearly coplanar with the phenyl, as shown by the C15—C16—N21—O22 [3.9 (4)°] and C17—C18—N24—O25 [2.9 (5)°] torsion angles. The angles between the plane of the three-atom bridge, C1/C10/C7, and the four-atom planes (C1/C9/C8/C7 and C1/C2/C6/C7) of the six-membered ring are 53.6 (2) and 58.1 (2)°, respectively. The dihedral angle between the norbornene ring and ring C is 30.2 (1)°. The C11—C12—N13—N14, C12—N13—N14—C15 and N13—N14—C15—C16 torsion angles are all (-)antiperiplanar [-178.8 (3)°, -178.9 (3)° and -178.5 (3)°, respectively]. The torsion angles C3—C11—C12—N13 and C2—C3—C11—C12, which define the orientation of the tricycle substituent with respect to the central chain, are -111.7 (4) and 64.7 (4)°, respectively.

The packing of the molecules of (III) viewed down the a axis is shown in Fig. 2 and details of the hydrogen bonds are given in Table 1. The weak N14—H14···O22ⁱ interaction joins the molecules into centrosymmetric dimers, causing an O22···O22ⁱ contact of 2.69 (4) Å, a little shorter than the sum of the van der Waals radii (2.80 Å; Pauling, 1960).

S2. Experimental

Vinyl ether, (I) (348 mg, 0.2 mmol), was treated with 3M LPDE Please define (10 ml) and stirred at room temperature for 3 h. The reaction mixture was quenched with iced water and extracted with dichloromethane (3 × 10 ml). The combined organic extracts were washed with water, dried over anhydrous sodium sulfate and purified using flash column chromatography, to yield 0.25 g of the aldehyde. A sample of the aldehyde, (II), was treated with 2,4-dinitrophenylhydrazine in methanol, whereby the hydrazine derivative, (III), precipitated out. Crystals of (III) suitable for X-ray diffraction studies were grown by slow evaporation from ethyl acetate-hexane (2:1) solution. Spectroscopic analysis: IR (pure sample, cm^-1): 2720 (C—H aldehydic), 1710 (C═O); ¹H NMR (400 MHz, C₆D₆, δ, p.p.m.): 9.1 (t, J = 1.46 Hz, 1H), 5.7 (dd, J = 5.87 and 2.93 Hz, 1H), 5.65 (dd, J = 5.87 and 2.93 Hz, 1H), 5.15 (dt, J = 5.85 and 2.92 Hz, 1H), 5.1 (dt, J = 585 and 2.93 Hz, 1H), 2.3 (m, 2H), 2.13 (m, 2H), 1.60 (m, 2H), 1.3 (m, 2H), 1.2–1.0 (m, 1H); ¹³C NMR (100.5 MHz, C₆D₆, δ, p.p.m.): 200.43 (d), 137.97 (d), 137.72 (d), 136.53 (d), 133.60 (d), 54.53 (d), 51.03 (t), 50.41 (d), 48.20 (d), 46.11 (d), 44.36 (d), 42.62 (t).

S3. Refinement

All H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, refined using a riding model, and given an isotropic displacement parameter equal to 1.2 times the equivalent isotropic parameter of the parent C—H groups.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (III) with displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram for (III), viewed down the a axis, showing the N—H···O hydrogen bonds.

2-(exo-Tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-endo-yl)acetaldehyde 2,4-dinitrophenylhydrazone

Crystal data

C18H18N4O4	F(000) = 744
Mr = 354.36	Dx = 1.363 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 6.412 (1) Å	Cell parameters from 25 reflections
b = 14.569 (2) Å	θ = 14–30°
c = 19.144 (3) Å	µ = 0.82 mm^−1
β = 105.02 (1)°	T = 293 K
V = 1727.4 (4) Å^3	Needle, yellow
Z = 4	0.30 × 0.25 × 0.13 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1973 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 69.9°, θmin = 3.9°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.880, Tmax = 0.899	l = −7→23
3300 measured reflections	3 standard reflections every 120 min
3206 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.214	w = 1/[σ^2(Fo^2) + (0.118P)^2 + 0.5657P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3306 reflections	Δρmax = 0.36 e Å^−3
236 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (8)

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
C1	0.6104 (6)	0.4045 (2)	0.80733 (19)	0.0669 (9)
H1	0.4929	0.3768	0.7701	0.080*
C2	0.6054 (5)	0.5101 (2)	0.81235 (15)	0.0521 (8)
H2	0.6644	0.5378	0.7749	0.063*
C3	0.3893 (6)	0.5550 (2)	0.81260 (16)	0.0593 (8)
H3	0.2764	0.5079	0.8032	0.071*
C4	0.4250 (7)	0.5889 (3)	0.88937 (19)	0.0729 (10)
H4	0.3175	0.6168	0.9065	0.087*
C5	0.6173 (8)	0.5757 (3)	0.92880 (19)	0.0753 (11)
H5	0.6630	0.5941	0.9769	0.090*
C6	0.7626 (6)	0.5273 (2)	0.88977 (18)	0.0619 (9)
H6	0.8880	0.5646	0.8876	0.074*
C7	0.8262 (6)	0.4296 (2)	0.91670 (18)	0.0620 (9)
H7	0.8880	0.4228	0.9689	0.074*
C8	0.9605 (7)	0.3925 (3)	0.8689 (2)	0.0775 (11)
H8	1.1084	0.3815	0.8830	0.093*
C9	0.8331 (7)	0.3787 (3)	0.8044 (2)	0.0728 (10)
H9	0.8737	0.3568	0.7642	0.087*
C10	0.6200 (6)	0.3770 (2)	0.8851 (2)	0.0689 (10)
H10A	0.4984	0.3999	0.9014	0.083*
H10B	0.6360	0.3114	0.8932	0.083*
C11	0.3191 (6)	0.6332 (3)	0.75893 (17)	0.0676 (10)
H11A	0.1902	0.6612	0.7671	0.081*
H11B	0.4317	0.6795	0.7683	0.081*
C12	0.2736 (6)	0.6049 (2)	0.68187 (16)	0.0600 (8)
H12	0.1549	0.5680	0.6617	0.072*
N13	0.3959 (4)	0.63098 (18)	0.64402 (13)	0.0557 (7)
N14	0.3403 (4)	0.60320 (17)	0.57229 (13)	0.0533 (6)
H14	0.2264	0.5707	0.5554	0.064*
C15	0.4681 (5)	0.62800 (19)	0.52941 (16)	0.0489 (7)
C16	0.4255 (5)	0.60559 (19)	0.45516 (15)	0.0463 (7)
C17	0.5593 (5)	0.6339 (2)	0.41305 (18)	0.0542 (8)
H17	0.5265	0.6195	0.3641	0.065*
C18	0.7404 (5)	0.6834 (2)	0.44444 (19)	0.0569 (8)
C19	0.7918 (5)	0.7056 (2)	0.5171 (2)	0.0622 (9)
H19	0.9163	0.7390	0.5375	0.075*
C20	0.6591 (5)	0.6784 (2)	0.55892 (18)	0.0573 (8)
H20	0.6955	0.6934	0.6078	0.069*
N21	0.2393 (4)	0.55250 (18)	0.41859 (13)	0.0521 (6)
O22	0.1074 (4)	0.52992 (16)	0.45252 (11)	0.0609 (6)
O23	0.2178 (4)	0.52949 (19)	0.35571 (12)	0.0768 (8)
N24	0.8798 (5)	0.7136 (2)	0.3998 (2)	0.0744 (9)
O25	0.8277 (5)	0.6973 (3)	0.33548 (19)	0.1089 (11)
O26	1.0456 (5)	0.75424 (19)	0.42982 (18)	0.0915 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.073 (2)	0.060 (2)	0.064 (2)	−0.0031 (17)	0.0114 (17)	−0.0136 (16)
C2	0.066 (2)	0.0511 (17)	0.0388 (14)	0.0007 (14)	0.0125 (13)	0.0024 (12)
C3	0.063 (2)	0.0632 (19)	0.0512 (17)	0.0058 (16)	0.0139 (15)	−0.0014 (15)
C4	0.084 (3)	0.081 (3)	0.060 (2)	0.013 (2)	0.030 (2)	−0.0063 (18)
C5	0.113 (3)	0.061 (2)	0.0479 (18)	0.002 (2)	0.013 (2)	−0.0080 (15)
C6	0.065 (2)	0.0561 (19)	0.0575 (18)	−0.0121 (16)	0.0042 (15)	0.0021 (15)
C7	0.061 (2)	0.067 (2)	0.0526 (17)	−0.0045 (17)	0.0065 (15)	0.0127 (15)
C8	0.070 (2)	0.076 (2)	0.088 (3)	0.015 (2)	0.023 (2)	0.027 (2)
C9	0.082 (3)	0.065 (2)	0.077 (2)	0.0220 (19)	0.030 (2)	0.0078 (18)
C10	0.073 (2)	0.0535 (19)	0.085 (2)	−0.0070 (17)	0.0287 (19)	0.0051 (18)
C11	0.082 (3)	0.065 (2)	0.0563 (19)	0.0165 (18)	0.0192 (17)	0.0021 (16)
C12	0.063 (2)	0.061 (2)	0.0514 (17)	0.0072 (16)	0.0075 (15)	0.0077 (15)
N13	0.0627 (17)	0.0537 (15)	0.0486 (14)	0.0048 (12)	0.0108 (12)	−0.0004 (11)
N14	0.0559 (16)	0.0541 (15)	0.0485 (13)	0.0003 (12)	0.0111 (11)	−0.0005 (11)
C15	0.0494 (17)	0.0391 (15)	0.0570 (17)	0.0062 (12)	0.0120 (13)	0.0039 (12)
C16	0.0442 (16)	0.0408 (15)	0.0531 (16)	0.0007 (12)	0.0110 (13)	0.0020 (12)
C17	0.0498 (18)	0.0493 (16)	0.0653 (19)	0.0040 (14)	0.0184 (15)	0.0037 (14)
C18	0.0505 (19)	0.0454 (16)	0.080 (2)	0.0013 (13)	0.0265 (16)	0.0033 (15)
C19	0.0499 (19)	0.0461 (17)	0.089 (2)	−0.0030 (14)	0.0158 (17)	−0.0051 (16)
C20	0.0563 (19)	0.0469 (16)	0.0648 (19)	0.0013 (14)	0.0086 (15)	−0.0061 (14)
N21	0.0500 (15)	0.0536 (15)	0.0516 (14)	−0.0024 (11)	0.0110 (11)	0.0038 (11)
O22	0.0562 (13)	0.0673 (14)	0.0612 (13)	−0.0153 (11)	0.0188 (10)	0.0003 (10)
O23	0.0778 (17)	0.101 (2)	0.0517 (13)	−0.0260 (15)	0.0172 (11)	−0.0112 (13)
N24	0.0575 (19)	0.0648 (18)	0.109 (3)	−0.0027 (15)	0.0356 (18)	0.0114 (18)
O25	0.094 (2)	0.147 (3)	0.099 (2)	−0.031 (2)	0.0501 (19)	0.004 (2)
O26	0.0628 (17)	0.0729 (17)	0.144 (3)	−0.0125 (14)	0.0364 (17)	0.0116 (17)

Geometric parameters (Å, º)

C1—C9	1.492 (5)	C11—C12	1.486 (4)
C1—C10	1.527 (5)	C11—H11A	0.9700
C1—C2	1.542 (5)	C11—H11B	0.9700
C1—H1	0.9800	C12—N13	1.256 (4)
C2—C3	1.534 (4)	C12—H12	0.9300
C2—C6	1.582 (4)	N13—N14	1.387 (3)
C2—H2	0.9800	N14—C15	1.351 (4)
C3—C4	1.511 (4)	N14—H14	0.8600
C3—C11	1.522 (4)	C15—C16	1.414 (4)
C3—H3	0.9800	C15—C20	1.415 (4)
C4—C5	1.283 (5)	C16—C17	1.384 (4)
C4—H4	0.9300	C16—N21	1.442 (4)
C5—C6	1.511 (5)	C17—C18	1.367 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.533 (5)	C18—C19	1.382 (5)
C6—H6	0.9800	C18—N24	1.456 (4)
C7—C8	1.509 (5)	C19—C20	1.369 (5)
C7—C10	1.512 (5)	C19—H19	0.9300
C7—H7	0.9800	C20—H20	0.9300
C8—C9	1.309 (5)	N21—O23	1.222 (3)
C8—H8	0.9300	N21—O22	1.237 (3)
C9—H9	0.9300	N24—O25	1.212 (4)
C10—H10A	0.9700	N24—O26	1.223 (4)
C10—H10B	0.9700
C9—C1—C10	100.0 (3)	C7—C10—H10A	112.9
C9—C1—C2	106.8 (3)	C1—C10—H10A	112.9
C10—C1—C2	101.4 (3)	C7—C10—H10B	112.9
C9—C1—H1	115.6	C1—C10—H10B	112.9
C10—C1—H1	115.6	H10A—C10—H10B	110.4
C2—C1—H1	115.6	C12—C11—C3	114.2 (3)
C3—C2—C1	117.3 (3)	C12—C11—H11A	108.7
C3—C2—C6	106.6 (2)	C3—C11—H11A	108.7
C1—C2—C6	101.5 (3)	C12—C11—H11B	108.7
C3—C2—H2	110.3	C3—C11—H11B	108.7
C1—C2—H2	110.3	H11A—C11—H11B	107.6
C6—C2—H2	110.3	N13—C12—C11	119.9 (3)
C4—C3—C11	110.8 (3)	N13—C12—H12	120.1
C4—C3—C2	103.5 (3)	C11—C12—H12	120.1
C11—C3—C2	115.3 (3)	C12—N13—N14	116.4 (3)
C4—C3—H3	109.0	C15—N14—N13	118.9 (3)
C11—C3—H3	109.0	C15—N14—H14	120.5
C2—C3—H3	109.0	N13—N14—H14	120.5
C5—C4—C3	113.8 (3)	N14—C15—C16	124.0 (3)
C5—C4—H4	123.1	N14—C15—C20	119.7 (3)
C3—C4—H4	123.1	C16—C15—C20	116.3 (3)
C4—C5—C6	113.6 (3)	C17—C16—C15	122.0 (3)
C4—C5—H5	123.2	C17—C16—N21	115.9 (3)
C6—C5—H5	123.2	C15—C16—N21	122.1 (3)
C5—C6—C7	114.3 (3)	C18—C17—C16	119.0 (3)
C5—C6—C2	102.3 (3)	C18—C17—H17	120.5
C7—C6—C2	102.5 (2)	C16—C17—H17	120.5
C5—C6—H6	112.3	C17—C18—C19	121.3 (3)
C7—C6—H6	112.3	C17—C18—N24	118.8 (3)
C2—C6—H6	112.3	C19—C18—N24	119.9 (3)
C8—C7—C10	98.9 (3)	C20—C19—C18	119.9 (3)
C8—C7—C6	105.8 (3)	C20—C19—H19	120.1
C10—C7—C6	101.9 (3)	C18—C19—H19	120.1
C8—C7—H7	116.0	C19—C20—C15	121.5 (3)
C10—C7—H7	116.0	C19—C20—H20	119.3
C6—C7—H7	116.0	C15—C20—H20	119.3
C9—C8—C7	108.2 (3)	O23—N21—O22	121.7 (3)
C9—C8—H8	125.9	O23—N21—C16	119.5 (3)
C7—C8—H8	125.9	O22—N21—C16	118.7 (2)
C8—C9—C1	107.2 (3)	O25—N24—O26	123.4 (3)
C8—C9—H9	126.4	O25—N24—C18	119.2 (3)
C1—C9—H9	126.4	O26—N24—C18	117.4 (4)
C7—C10—C1	93.9 (3)
C9—C1—C2—C3	177.3 (3)	C2—C1—C10—C7	−58.3 (3)
C10—C1—C2—C3	−78.5 (3)	C4—C3—C11—C12	−178.1 (3)
C9—C1—C2—C6	−67.0 (3)	C2—C3—C11—C12	64.8 (4)
C10—C1—C2—C6	37.2 (3)	C3—C11—C12—N13	−111.6 (4)
C1—C2—C3—C4	108.9 (3)	C11—C12—N13—N14	−178.8 (3)
C6—C2—C3—C4	−3.9 (3)	C12—N13—N14—C15	−178.9 (3)
C1—C2—C3—C11	−130.0 (3)	N13—N14—C15—C16	−178.5 (3)
C6—C2—C3—C11	117.2 (3)	N13—N14—C15—C20	2.4 (4)
C11—C3—C4—C5	−120.7 (4)	N14—C15—C16—C17	178.8 (3)
C2—C3—C4—C5	3.4 (4)	C20—C15—C16—C17	−2.1 (4)
C3—C4—C5—C6	−1.2 (5)	N14—C15—C16—N21	−0.6 (4)
C4—C5—C6—C7	−111.3 (4)	C20—C15—C16—N21	178.4 (3)
C4—C5—C6—C2	−1.4 (4)	C15—C16—C17—C18	1.4 (4)
C3—C2—C6—C5	3.3 (3)	N21—C16—C17—C18	−179.1 (3)
C1—C2—C6—C5	−120.0 (3)	C16—C17—C18—C19	−0.1 (5)
C3—C2—C6—C7	121.9 (3)	C16—C17—C18—N24	−179.6 (3)
C1—C2—C6—C7	−1.4 (3)	C17—C18—C19—C20	−0.4 (5)
C5—C6—C7—C8	177.4 (3)	N24—C18—C19—C20	179.1 (3)
C2—C6—C7—C8	67.6 (3)	C18—C19—C20—C15	−0.3 (5)
C5—C6—C7—C10	74.5 (3)	N14—C15—C20—C19	−179.3 (3)
C2—C6—C7—C10	−35.3 (3)	C16—C15—C20—C19	1.5 (4)
C10—C7—C8—C9	34.7 (4)	C17—C16—N21—O23	5.6 (4)
C6—C7—C8—C9	−70.5 (4)	C15—C16—N21—O23	−174.9 (3)
C7—C8—C9—C1	−0.9 (4)	C17—C16—N21—O22	−175.8 (3)
C10—C1—C9—C8	−33.0 (4)	C15—C16—N21—O22	3.7 (4)
C2—C1—C9—C8	72.2 (4)	C17—C18—N24—O25	2.9 (5)
C8—C7—C10—C1	−50.9 (3)	C19—C18—N24—O25	−176.7 (4)
C6—C7—C10—C1	57.5 (3)	C17—C18—N24—O26	−176.8 (3)
C9—C1—C10—C7	51.2 (3)	C19—C18—N24—O26	3.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O22	0.86	2.01	2.618 (3)	127
N14—H14···O22^i	0.86	2.57	3.395 (4)	162

Symmetry code: (i) −x, −y+1, −z+1.