fac-Bromo­tri­carbonyl­[2-(2-pyridylmethyl)-2,3-di­hydro-1H-isoindol-1-one]­rhenium(I) methanol solvate

The structure of the title compound, fac-[ReBr(C₁₄H₁₂N₂O)(CO)₃]·CH₄O, consists of neutral mononuclear mol­ecular units of distorted octahedral geometry, with the three carbonyl donors in a facial orientation. The remaining coordination sites are occupied by the Br atom, the pyridine N atom and the ketone O-atom donor of the ligand. The mol­ecules pack in stacks of antiparallel tapes, with a network of classical (O—H...Br) and non-classical (C—H...O) hydrogen bonds between the methanol solvent mol­ecule and the complex mol­ecule.

S1. Comment

The ligand 2-pyridin-2-yl-methyl-2,3-dihydro-isoindol-1-one [C₁₄H₁₂N₂O, (I)] was an unexpected product from the reaction of 2-(aminomethyl) pyridine with 2-carboxybenzaldehyde, NaOH and sodium borohydride in methanol (see scheme). Following the literature procedure (Li et al., 2003; Musie et al., 2003), we attempted to prepare N-(2-methylpyridine)-2-aminomethyl benzoic acid, (III). Although one equivalent of NaOH was added to protect the carboxylic acid group, a coupling reaction between the carboxylic acid group and the primary amine group occurred, forming intermediate 1. Condensation of the carboxyaldehyde and the amine group of 1 provided Schiff base 2, which upon reduction using sodium borohydride in methanol gave the ligand (I). Complex (II) was synthesized upon refluxing a methanol solution of the common Re(I)–tricarbonyl starting material [NEt₄]₂[Re(CO)₃Br₃] (Alberto et al., 1994) with (I). The structure of complex (II) is shown in Fig. 1, and selected bond lengths and angles are given in Table 1.

The ligand adopts a bidentate coordination mode through the pyridine N atom and the ketone O atom to form an unusual seven-membered chelate ring. The formation of the seven-membered ring illustrates the flexibility of the ligand. The ligand folds at the methylene group adjacent to the pyridine ring (C9), thus providing appropriate chelate bite distances and angles. The Re—C_carbonyl bond distances [1.898 (3)–1.910 (4) Å] are consistent with those found in other Re–tricarbonyl complexes (Banerjee et al., 2002; Wei et al., 2004; Moya et al., 1994). The Re—Br [2.6409 (4) Å] and Re—N_pyridine [2.239 (3) Å] bond lengths are comparable to those of 6-coordinated Re compounds with ligands trans to carbonyl groups (Banerjee et al., 2002; Wei et al., 2004). For example, in [Re(CO)₃Br{(2-pyridylmethyl)NH₂}] and [Re(CO)₃Br{(2-pyridylmethyl)NH(2-thiophenemethyl)}], the average Re—Br and Re—N_pyridine bond distances are 2.636 (6) Å and 2.190 (4) Å, respectively (Banerjee et al., 2002). The C10=O4 bond length in (II) [1.248 (3) Å] is as expected for a C=O double bond. The Re—O bond distance [2.182 (2) Å] lies within the range of the bond lengths between Re and ketone O atoms reported previously (Creber et al., 2000; Wang et al., 2003; Jiménez et al., 2001). The cis and trans angles fall in the ranges 82.85 (6)–98.41 (12) and 172.06 (12)–177.57 (10)°, respectively, showing minor deviations from the idealized octahedral limits. The steric requirement of the CO ligands is manifested in the mean C—Re—N and C—Re—O cis angles of 94.0 (4)° and in the mean C—Re—N and C—Re—O trans angles of 174.2 (1)°.

The crystal packing consists of antiparallel stacks of (II), with a network of hydrogen bonds between the methanol solvate and adjacent fac-[Re(CO)₃Br(C₁₄H₁₂N₂O)] molecules (Table 2). This arrangement leads to the formation of a classical intramolecular O—H···Br hydrogen bond and intermolecular non-classical C—H···O hydrogen bonds (Fig. 2). The bond distances and angles of the hydrogen bonds are of the same order as those reported in other compounds containing such bonds (Bakir, 2001; Bakir, 2002; Correia et al., 2001). For example, in fac-[ReCl(C₁₇H₁₃N₅O₂)(CO)₃]·C₂H₆OS (Bakir, 2001), hydrogen bonds with O—H and O—C distances of 2.47—2.55 and 3.183 (7)–3.436 (7) Å, respectively, and C—H···O angles of 142–174° are observed.

S2. Experimental

For the preparation of ligand (I), 2-(aminomethyl)pyridine (2.88 g, 25.85 mmol) was added to a stirred solution of 2-carboxybenzaldehyde (4.00 g, 26.64 mmol) and NaOH (1.07 g, 26.64 mmol) in methanol (50 ml). The solution was refluxed at 323 K for 2 h, whereupon the solution turned yellow and was cooled in an ice-bath. Excess NaBH₄ (1.24 g, 32.72 mmol) was added to the solution, and the yellow color slowly discharged. After stirring for 30 min, excess HCl was added until the pH of the solution was 5.0. The solution was filtered and the filtrate was evaporated to dryness. The residue was purified by silica gel column chromatography using CH₃OH/CH₂Cl₂ (5:95) to give (I) (yield 4.4 g, 76%). For the preparation of (II), ligand (I) (0.07 g, 0.33 mmol) was added to a solution of [NEt₄]₂[Re(CO)₃Br₃] (0.25 g, 0.33 mmol) in methanol (30 ml), and the solution was refluxed for 2 h. After cooling to room temperature, the reaction mixture was evaporated to dryness. The residue was dissolved in a minimum amount of chloroform. Colorless crystals suitable for X-ray crystallography were obtained from the solution after 30 min (yield 0.15 g, 80%). Analysis found: C 35.6, H 2.23, N 4.76%; calculated: C 35.5, H 2.11, N 4.88%. IR (KBr, cm⁻¹): ν 2026, 1997, 1868 {ν[fac-Re(CO)₃]}.

S3. Refinement

All H atoms were located in difference Fourier maps and refined as riding on their parent atoms? (C—H = 0.93–0.77 Å), with U_iso(H) values of 1.2U_eq(parent atom). A residual peak of electron density (1.64 e Å⁻³) was located in the vicinity of the Re atom. However, the absorption correction could not be adjusted to further minimize this residual. Such residuals are not uncommon in structures containing atoms with large absorption coefficients.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-NT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2000); software used to prepare material for publication: SHELXTL-NT.

Figures

	Fig. 1. A view of the structure of complex (II), showing the atom-labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. A view showing classical and non-classical hydrogen bonds in (II). [Symmetry codes: (A) x, y, z; (B) 1/2 + x, 3/2 − y, 1/2 + z; (C) −1 − x, 2 − y, −z.]

(II)

Crystal data

[ReBr(C14H12N2O)(CO)3]·CH3OH	F(000) = 1152
Mr = 606.44	Dx = 2.165 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6164 reflections
a = 7.3195 (7) Å	θ = 1.8–31.5°
b = 15.5186 (14) Å	µ = 8.71 mm^−1
c = 16.4240 (15) Å	T = 90 K
β = 94.182 (2)°	Block, colorless
V = 1860.6 (3) Å^3	0.24 × 0.14 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD detector diffractometer	6164 independent reflections
Radiation source: fine-focus sealed tube	5404 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 512 pixels mm^-1	θmax = 31.5°, θmin = 1.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −22→22
Tmin = 0.229, Tmax = 0.421	l = −23→23
21761 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0314P)^2 + 0.1451P] where P = (Fo^2 + 2Fc^2)/3
6164 reflections	(Δ/σ)max = 0.002
246 parameters	Δρmax = 1.64 e Å^−3
0 restraints	Δρmin = −0.81 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
Re1	−0.130324 (16)	0.846209 (7)	0.092222 (7)	0.01236 (4)
Br1	−0.43226 (4)	0.75261 (2)	0.08734 (2)	0.01835 (7)
N1	−0.1569 (4)	0.82914 (16)	−0.04347 (16)	0.0138 (5)
N2	0.1569 (3)	0.68839 (16)	−0.01211 (15)	0.0127 (5)
O1	−0.1306 (4)	0.84466 (16)	0.27846 (16)	0.0289 (6)
O2	0.2191 (4)	0.95403 (17)	0.10857 (17)	0.0307 (6)
O3	−0.3282 (4)	1.01925 (16)	0.08551 (17)	0.0307 (6)
O4	0.0020 (3)	0.72027 (13)	0.10224 (13)	0.0143 (4)
O5	0.2457 (4)	0.87471 (19)	0.73288 (17)	0.0288 (6)
H5	0.2404	0.8407	0.6946	0.043*
C1	−0.1287 (5)	0.8469 (2)	0.2084 (2)	0.0182 (6)
C2	0.0900 (5)	0.9126 (2)	0.1005 (2)	0.0197 (6)
C3	−0.2567 (5)	0.9531 (2)	0.0881 (2)	0.0214 (7)
C4	−0.3217 (4)	0.8490 (2)	−0.08119 (19)	0.0158 (6)
H4	−0.4090	0.8742	−0.0504	0.019*
C5	−0.3674 (5)	0.8337 (2)	−0.1629 (2)	0.0190 (7)
H5A	−0.4834	0.8475	−0.1861	0.023*
C6	−0.2384 (5)	0.7976 (2)	−0.2095 (2)	0.0200 (7)
H6	−0.2662	0.7856	−0.2645	0.024*
C7	−0.0666 (5)	0.7795 (2)	−0.17272 (19)	0.0182 (6)
H7	0.0236	0.7563	−0.2033	0.022*
C8	−0.0289 (4)	0.79598 (19)	−0.09030 (19)	0.0139 (6)
C9	0.1560 (4)	0.77363 (19)	−0.04950 (18)	0.0129 (5)
H9A	0.2468	0.7754	−0.0896	0.015*
H9B	0.1895	0.8163	−0.0079	0.015*
C10	0.0888 (4)	0.67047 (19)	0.05949 (18)	0.0116 (5)
C11	0.1367 (4)	0.58012 (19)	0.08062 (18)	0.0132 (5)
C12	0.2299 (4)	0.54660 (19)	0.01705 (19)	0.0132 (5)
C13	0.2489 (4)	0.61458 (19)	−0.04629 (19)	0.0146 (6)
H13A	0.3766	0.6271	−0.0532	0.018*
H13B	0.1891	0.5975	−0.0984	0.018*
C14	0.1008 (4)	0.5327 (2)	0.14925 (19)	0.0161 (6)
H14	0.0377	0.5564	0.1910	0.019*
C15	0.1638 (4)	0.4480 (2)	0.1526 (2)	0.0175 (6)
H15	0.1461	0.4144	0.1983	0.021*
C16	0.2529 (4)	0.4129 (2)	0.0883 (2)	0.0180 (6)
H16	0.2914	0.3558	0.0914	0.022*
C17	0.2859 (4)	0.4610 (2)	0.0195 (2)	0.0166 (6)
H17	0.3437	0.4367	−0.0236	0.020*
C18	0.1110 (5)	0.9402 (2)	0.7179 (2)	0.0287 (8)
H18A	0.0698	0.9598	0.7689	0.043*
H18B	0.0092	0.9173	0.6846	0.043*
H18C	0.1634	0.9876	0.6901	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01328 (6)	0.01081 (6)	0.01285 (6)	0.00211 (4)	0.00001 (4)	−0.00170 (4)
Br1	0.01366 (13)	0.01971 (15)	0.02155 (15)	−0.00052 (11)	0.00033 (11)	0.00112 (12)
N1	0.0148 (12)	0.0106 (11)	0.0158 (12)	0.0008 (9)	−0.0005 (9)	0.0007 (9)
N2	0.0130 (11)	0.0106 (11)	0.0144 (12)	0.0021 (9)	0.0014 (9)	−0.0008 (9)
O1	0.0413 (16)	0.0287 (14)	0.0171 (12)	0.0037 (12)	0.0040 (11)	−0.0011 (10)
O2	0.0283 (13)	0.0245 (14)	0.0393 (16)	−0.0083 (11)	0.0020 (12)	−0.0052 (12)
O3	0.0382 (15)	0.0211 (13)	0.0320 (15)	0.0138 (12)	−0.0019 (12)	−0.0024 (11)
O4	0.0144 (10)	0.0124 (10)	0.0166 (10)	0.0037 (8)	0.0032 (8)	0.0000 (8)
O5	0.0233 (12)	0.0341 (15)	0.0285 (14)	0.0000 (11)	−0.0024 (11)	−0.0064 (12)
C1	0.0188 (15)	0.0133 (14)	0.0222 (16)	0.0037 (12)	0.0002 (12)	−0.0024 (12)
C2	0.0244 (16)	0.0159 (15)	0.0187 (16)	0.0030 (13)	0.0016 (12)	−0.0024 (12)
C3	0.0228 (16)	0.0212 (17)	0.0197 (16)	0.0051 (13)	−0.0012 (12)	−0.0037 (13)
C4	0.0152 (13)	0.0160 (15)	0.0161 (14)	0.0032 (11)	0.0001 (11)	0.0006 (11)
C5	0.0175 (14)	0.0196 (16)	0.0188 (15)	0.0007 (12)	−0.0059 (12)	0.0073 (12)
C6	0.0257 (16)	0.0211 (16)	0.0126 (14)	0.0004 (13)	−0.0036 (12)	0.0026 (12)
C7	0.0220 (15)	0.0197 (16)	0.0132 (14)	0.0016 (12)	0.0034 (11)	0.0039 (12)
C8	0.0162 (13)	0.0113 (13)	0.0144 (14)	0.0003 (11)	0.0032 (11)	0.0019 (11)
C9	0.0126 (12)	0.0127 (13)	0.0135 (13)	−0.0006 (10)	0.0022 (10)	0.0031 (11)
C10	0.0090 (12)	0.0114 (13)	0.0141 (13)	−0.0013 (10)	−0.0007 (10)	0.0000 (10)
C11	0.0100 (12)	0.0132 (13)	0.0158 (14)	0.0013 (10)	−0.0020 (10)	−0.0021 (11)
C12	0.0102 (12)	0.0107 (13)	0.0184 (14)	0.0020 (10)	−0.0009 (10)	0.0003 (11)
C13	0.0128 (13)	0.0151 (14)	0.0161 (14)	0.0024 (11)	0.0018 (11)	−0.0014 (11)
C14	0.0170 (14)	0.0152 (14)	0.0160 (14)	−0.0001 (11)	0.0005 (11)	0.0014 (11)
C15	0.0171 (14)	0.0144 (14)	0.0207 (15)	0.0002 (12)	−0.0003 (11)	0.0040 (12)
C16	0.0136 (13)	0.0123 (14)	0.0276 (17)	0.0003 (11)	−0.0009 (12)	−0.0015 (12)
C17	0.0129 (13)	0.0140 (14)	0.0226 (15)	0.0038 (11)	0.0006 (11)	−0.0033 (12)
C18	0.0308 (19)	0.0226 (18)	0.033 (2)	0.0050 (15)	0.0016 (15)	0.0023 (15)

Geometric parameters (Å, º)

Re1—C3	1.898 (3)	C7—C8	1.385 (4)
Re1—C1	1.907 (3)	C7—H7	0.9300
Re1—C2	1.910 (4)	C8—C9	1.506 (4)
Re1—O4	2.182 (2)	C9—H9A	0.9700
Re1—N1	2.239 (3)	C9—H9B	0.9700
Re1—Br1	2.6409 (4)	C10—C11	1.480 (4)
N1—C4	1.351 (4)	C11—C14	1.387 (4)
N1—C8	1.356 (4)	C11—C12	1.389 (4)
N2—C10	1.340 (4)	C12—C17	1.390 (4)
N2—C9	1.458 (4)	C12—C13	1.495 (4)
N2—C13	1.461 (4)	C13—H13A	0.9700
O1—C1	1.152 (4)	C13—H13B	0.9700
O2—C2	1.143 (4)	C14—C15	1.394 (4)
O3—C3	1.151 (4)	C14—H14	0.9300
O4—C10	1.248 (3)	C15—C16	1.392 (5)
O5—C18	1.425 (4)	C15—H15	0.9300
O5—H5	0.8200	C16—C17	1.389 (5)
C4—C5	1.380 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.377 (5)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—C7	1.384 (4)	C18—H18C	0.9600
C6—H6	0.9300
C3—Re1—C1	89.90 (14)	C7—C8—C9	120.0 (3)
C3—Re1—C2	86.44 (14)	N2—C9—C8	111.9 (2)
C1—Re1—C2	88.95 (14)	N2—C9—H9A	109.2
C3—Re1—O4	176.30 (12)	C8—C9—H9A	109.2
C1—Re1—O4	87.68 (11)	N2—C9—H9B	109.2
C2—Re1—O4	96.31 (11)	C8—C9—H9B	109.2
C3—Re1—N1	93.49 (12)	H9A—C9—H9B	107.9
C1—Re1—N1	172.06 (12)	O4—C10—N2	127.0 (3)
C2—Re1—N1	98.41 (12)	O4—C10—C11	125.2 (3)
O4—Re1—N1	88.56 (9)	N2—C10—C11	107.8 (3)
C3—Re1—Br1	94.30 (11)	C14—C11—C12	123.0 (3)
C1—Re1—Br1	88.73 (10)	C14—C11—C10	129.6 (3)
C2—Re1—Br1	177.57 (10)	C12—C11—C10	107.4 (3)
O4—Re1—Br1	82.85 (6)	C11—C12—C17	119.7 (3)
N1—Re1—Br1	83.86 (7)	C11—C12—C13	109.5 (3)
C4—N1—C8	117.2 (3)	C17—C12—C13	130.7 (3)
C4—N1—Re1	116.1 (2)	N2—C13—C12	102.5 (2)
C8—N1—Re1	126.6 (2)	N2—C13—H13A	111.3
C10—N2—C9	124.6 (3)	C12—C13—H13A	111.3
C10—N2—C13	112.7 (2)	N2—C13—H13B	111.3
C9—N2—C13	122.5 (2)	C12—C13—H13B	111.3
C10—O4—Re1	138.9 (2)	H13A—C13—H13B	109.2
C18—O5—H5	109.5	C11—C14—C15	116.8 (3)
O1—C1—Re1	177.7 (3)	C11—C14—H14	121.6
O2—C2—Re1	176.9 (3)	C15—C14—H14	121.6
O3—C3—Re1	177.8 (3)	C16—C15—C14	120.7 (3)
N1—C4—C5	123.5 (3)	C16—C15—H15	119.6
N1—C4—H4	118.2	C14—C15—H15	119.6
C5—C4—H4	118.2	C17—C16—C15	121.7 (3)
C6—C5—C4	118.9 (3)	C17—C16—H16	119.1
C6—C5—H5A	120.6	C15—C16—H16	119.1
C4—C5—H5A	120.6	C16—C17—C12	117.9 (3)
C5—C6—C7	118.5 (3)	C16—C17—H17	121.0
C5—C6—H6	120.7	C12—C17—H17	121.0
C7—C6—H6	120.7	O5—C18—H18A	109.5
C6—C7—C8	119.9 (3)	O5—C18—H18B	109.5
C6—C7—H7	120.0	H18A—C18—H18B	109.5
C8—C7—H7	120.0	O5—C18—H18C	109.5
N1—C8—C7	121.9 (3)	H18A—C18—H18C	109.5
N1—C8—C9	118.1 (3)	H18B—C18—H18C	109.5
C3—Re1—N1—C4	−42.7 (2)	C7—C8—C9—N2	−93.7 (3)
C2—Re1—N1—C4	−129.6 (2)	Re1—O4—C10—N2	11.6 (5)
O4—Re1—N1—C4	134.2 (2)	Re1—O4—C10—C11	−169.3 (2)
Br1—Re1—N1—C4	51.2 (2)	C9—N2—C10—O4	6.2 (5)
C3—Re1—N1—C8	141.8 (3)	C13—N2—C10—O4	−179.1 (3)
C2—Re1—N1—C8	54.9 (3)	C9—N2—C10—C11	−173.1 (2)
O4—Re1—N1—C8	−41.2 (2)	C13—N2—C10—C11	1.6 (3)
Br1—Re1—N1—C8	−124.2 (2)	O4—C10—C11—C14	−0.9 (5)
C1—Re1—O4—C10	−163.6 (3)	N2—C10—C11—C14	178.3 (3)
C2—Re1—O4—C10	−74.9 (3)	O4—C10—C11—C12	179.0 (3)
N1—Re1—O4—C10	23.4 (3)	N2—C10—C11—C12	−1.8 (3)
Br1—Re1—O4—C10	107.4 (3)	C14—C11—C12—C17	2.2 (4)
C8—N1—C4—C5	2.9 (5)	C10—C11—C12—C17	−177.7 (3)
Re1—N1—C4—C5	−173.0 (2)	C14—C11—C12—C13	−178.9 (3)
N1—C4—C5—C6	−1.1 (5)	C10—C11—C12—C13	1.2 (3)
C4—C5—C6—C7	−1.2 (5)	C10—N2—C13—C12	−0.9 (3)
C5—C6—C7—C8	1.4 (5)	C9—N2—C13—C12	174.0 (2)
C4—N1—C8—C7	−2.6 (4)	C11—C12—C13—N2	−0.3 (3)
Re1—N1—C8—C7	172.8 (2)	C17—C12—C13—N2	178.5 (3)
C4—N1—C8—C9	179.9 (3)	C12—C11—C14—C15	0.3 (4)
Re1—N1—C8—C9	−4.7 (4)	C10—C11—C14—C15	−179.8 (3)
C6—C7—C8—N1	0.5 (5)	C11—C14—C15—C16	−2.0 (4)
C6—C7—C8—C9	178.0 (3)	C14—C15—C16—C17	1.4 (5)
C10—N2—C9—C8	−78.5 (3)	C15—C16—C17—C12	1.1 (5)
C13—N2—C9—C8	107.3 (3)	C11—C12—C17—C16	−2.8 (4)
N1—C8—C9—N2	83.9 (3)	C13—C12—C17—C16	178.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···Br1^i	0.82	2.54	3.296 (3)	153
C4—H4···O3^ii	0.93	2.57	3.275 (4)	133
C5—H5A···O5^iii	0.93	2.34	3.263 (5)	169
C14—H14···O5^iv	0.93	2.53	3.351 (4)	147

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