1-Octylindoline-2,3-dione

Qachchachi, F.-Z.; Kandri Rodi, Y.; Essassi, E.M.; Kunz, W.; El Ammari, L.

doi:10.1107/S1600536813031383

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1801

doi:10.1107/S1600536813031383

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1-Octylindoline-2,3-dione

Fatima-Zahrae Qachchachi,^a ^* Youssef Kandri Rodi,^a El Mokhtar Essassi,^b Werner Kunz ^c and Lahcen El Ammari ^d

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat, Morocco, ^cInstitute of Physical and Theoretical Chemistry, University of Regensburg, D-93040 Regensburg, Germany, and ^dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: fatimazahrae_qachchachi@yahoo.fr

(Received 12 November 2013; accepted 15 November 2013; online 23 November 2013)

In the title compound, C₁₆H₂₁NO₂, the indoline ring and the two ketone O atoms are approximately coplanar, the largest deviation from the mean plane being 0.063 (2) Å. The mean plane through the fused ring system is nearly perpendicular to the mean plane passing through the 1-octyl chain [dihedral angle = 77.53 (17)°]. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

CCDC reference: 972266

Related literature

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010 ); Malhotra et al. (2011 ); Da Silva et al. (2001 ); Ramachandran (2011 ); Smitha et al. (2008 ). For the structure of a related compound, see: Mamari et al. (2010 ).

Experimental

Crystal data

C₁₆H₂₁NO₂
M_r = 259.34
Monoclinic, P 2₁ /c
a = 20.266 (4) Å
b = 4.6925 (1) Å
c = 15.7807 (11) Å
β = 108.941 (18)°
V = 1419.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 123 K
0.31 × 0.07 × 0.04 mm

Data collection

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012 $[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995 )] T_min = 0.899, T_max = 0.979
13541 measured reflections
2811 independent reflections
2462 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.167
S = 1.18
2811 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.49	3.156 (3)	129
C6—H6⋯O2ⁱⁱ	0.93	2.57	3.260 (3)	131
C4—H4⋯O2ⁱⁱⁱ	0.93	2.55	3.470 (3)	170
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+3, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2012 $[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 972266

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813031383/rz5095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031383/rz5095Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031383/rz5095Isup3.cml

checkCIF report

Comment top

Isatin, 1H-indole-2,3-dione, is a heterocyclic compound of significant importance in medicinal chemistry. It is a synthetically versatile molecule, a precursor for a large number of pharmacologically active compounds. Isatin and its derivatives have aroused great attention in recent years due to their wide variety of biological activities, relevant to application as insecticides and fungicides and in a broad range of drug therapies, including anticancer drugs, antibiotics and antidepressants (Bhrigu et al., 2010; Malhotra et al., 2011; Da Silva et al., 2001; Ramachandran, 2011; Smitha et al., 2008). As a continuation of our research work devoted to the development of isatin derivatives (Mamari et al., 2010), we report in this paper the synthesis of a new indoline-2,3-dione derivative by action of alkyl halides to explore other applications.

The molecule of title compound is build up from a fused five- and six-membered rings linked to a 1-octyl chain and to two ketonic oxygen atoms as shown in Fig. 1. The indoline ring and the two ketonic oxygen atoms are nearly coplanar, with the largest deviation from the mean plane of 0.063 (2) Å for atom O2. The fused ring system plan is nearly perpendicular to the mean plane passing through the 1-octyl chain as indicated by the torsion angle C1–N1–C9–C10 of -93.2 (2)°. In the crystal, the molecules are linked by C–H···O hydrogen bonds (Table 1) to build a three-dimensional network as shown in Fig. 2.

Related literature top

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010); Malhotra et al. (2011); Da Silva et al. (2001); Ramachandran (2011); Smitha et al. (2008). For the structure of a related compound, see: Mamari et al. (2010).

Experimental top

To a solution of isatin (0.5 g, 3.4 mmol) dissolved in DMF (30 ml) was added 1-bromooctane (0.7 ml, 3.4 mmol), potassium carbonate (0.61 g, 4.4 mmol) and a catalytic amount of tetra-n-butylammonium bromide (0.1 g, 0.4 mmol). The mixture was stirred for 48 h and the reaction monitored by thin layer chromatography. The mixture was filtered and the solvent removed under vacuum. The solid obtained was recrystallized from ethanol to afford the title compound as orange crystals (yield: 72%; mp = 317 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2012); cell refinement: CrysAlis PRO (Oxford Diffraction, 2012); data reduction: CrysAlis PRO (Oxford Diffraction, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular plot the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Intermolecular hydrogen interactions (dashed lines) in the title compound. Atoms labelled with suffixes a, b and c are generated by the symmetry operators 1-x, 3-y, 1-z; x, 3/2-y, 1/2+z and x, 5/2-y, 1/2+z, respectively.

1-Octylindoline-2,3-dione top

Crystal data top

C₁₆H₂₁NO₂	F(000) = 560
M_r = 259.34	D_x = 1.214 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 317 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 20.266 (4) Å	Cell parameters from 5321 reflections
b = 4.6925 (1) Å	θ = 3.0–73.5°
c = 15.7807 (11) Å	µ = 0.63 mm⁻¹
β = 108.941 (18)°	T = 123 K
V = 1419.5 (3) Å³	Plate, orange
Z = 4	0.31 × 0.07 × 0.04 mm

Data collection top

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer	2811 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2462 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 20.7092 pixels mm^-1	θ_max = 73.7°, θ_min = 4.6°
ω scans	h = −24→25
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)]	k = −5→5
T_min = 0.899, T_max = 0.979	l = −17→19
13541 measured reflections

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0633P)² + 1.1901P] where P = (F_o² + 2F_c²)/3
2811 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₂₁NO₂	V = 1419.5 (3) Å³
M_r = 259.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 20.266 (4) Å	µ = 0.63 mm⁻¹
b = 4.6925 (1) Å	T = 123 K
c = 15.7807 (11) Å	0.31 × 0.07 × 0.04 mm
β = 108.941 (18)°

Data collection top

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer	2811 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)]	2462 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.979	R_int = 0.029
13541 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.18	Δρ_max = 0.49 e Å⁻³
2811 reflections	Δρ_min = −0.22 e Å⁻³
172 parameters

Special details top

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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.33354 (9)	0.7667 (4)	0.34657 (10)	0.0397 (4)
O2	0.44511 (8)	1.1900 (4)	0.42454 (10)	0.0385 (4)
N1	0.32574 (9)	0.7836 (4)	0.48939 (11)	0.0272 (4)
C1	0.35221 (11)	0.8574 (5)	0.42319 (14)	0.0299 (5)
C2	0.40999 (10)	1.0835 (5)	0.46468 (14)	0.0288 (5)
C3	0.40798 (10)	1.1295 (4)	0.55543 (13)	0.0258 (4)
C4	0.44509 (10)	1.3124 (5)	0.62281 (15)	0.0296 (5)
H4	0.4791	1.4325	0.6148	0.036*
C5	0.43015 (11)	1.3116 (5)	0.70275 (14)	0.0308 (5)
H5	0.4540	1.4343	0.7488	0.037*
C6	0.37992 (11)	1.1290 (5)	0.71428 (13)	0.0290 (5)
H6	0.3710	1.1310	0.7685	0.035*
C7	0.34230 (10)	0.9420 (5)	0.64691 (13)	0.0272 (4)
H7	0.3089	0.8196	0.6553	0.033*
C8	0.35685 (9)	0.9471 (4)	0.56786 (13)	0.0241 (4)
C9	0.26652 (10)	0.5930 (5)	0.47581 (15)	0.0303 (5)
H9A	0.2732	0.4819	0.5298	0.036*
H9B	0.2645	0.4618	0.4275	0.036*
C10	0.19768 (10)	0.7542 (5)	0.45315 (15)	0.0300 (5)
H10A	0.1940	0.8837	0.4039	0.036*
H10B	0.1976	0.8674	0.5045	0.036*
C11	0.13437 (10)	0.5572 (5)	0.42731 (15)	0.0305 (5)
H11A	0.1382	0.4262	0.4763	0.037*
H11B	0.1341	0.4455	0.3754	0.037*
C12	0.06565 (10)	0.7207 (5)	0.40574 (15)	0.0311 (5)
H12A	0.0651	0.8230	0.4589	0.037*
H12B	0.0635	0.8605	0.3597	0.037*
C13	0.00107 (10)	0.5314 (5)	0.37394 (15)	0.0317 (5)
H13A	0.0014	0.4298	0.3205	0.038*
H13B	0.0031	0.3912	0.4199	0.038*
C14	−0.06690 (11)	0.6980 (5)	0.35310 (15)	0.0327 (5)
H14A	−0.0683	0.8412	0.3082	0.039*
H14B	−0.0675	0.7962	0.4069	0.039*
C15	−0.13189 (11)	0.5123 (5)	0.31923 (16)	0.0358 (5)
H15A	−0.1306	0.3683	0.3638	0.043*
H15B	−0.1317	0.4154	0.2650	0.043*
C16	−0.19929 (12)	0.6838 (6)	0.29952 (18)	0.0429 (6)
H16A	−0.2386	0.5578	0.2788	0.064*
H16B	−0.2015	0.8234	0.2542	0.064*
H16C	−0.2001	0.7778	0.3532	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0396 (9)	0.0494 (10)	0.0293 (8)	0.0081 (7)	0.0102 (7)	−0.0051 (7)
O2	0.0303 (8)	0.0559 (11)	0.0335 (8)	0.0040 (7)	0.0160 (7)	0.0132 (7)
N1	0.0222 (8)	0.0314 (9)	0.0271 (9)	0.0000 (7)	0.0067 (7)	−0.0028 (7)
C1	0.0265 (10)	0.0372 (12)	0.0262 (10)	0.0098 (8)	0.0087 (8)	0.0014 (8)
C2	0.0224 (9)	0.0349 (11)	0.0297 (10)	0.0088 (8)	0.0092 (8)	0.0086 (9)
C3	0.0225 (9)	0.0285 (10)	0.0275 (10)	0.0050 (7)	0.0096 (8)	0.0072 (8)
C4	0.0207 (9)	0.0307 (11)	0.0364 (11)	−0.0008 (8)	0.0078 (8)	0.0049 (9)
C5	0.0267 (10)	0.0319 (11)	0.0312 (11)	0.0000 (8)	0.0059 (8)	−0.0013 (8)
C6	0.0275 (10)	0.0353 (11)	0.0243 (10)	0.0047 (8)	0.0084 (8)	0.0026 (8)
C7	0.0240 (9)	0.0306 (11)	0.0286 (10)	0.0001 (8)	0.0107 (8)	0.0031 (8)
C8	0.0188 (9)	0.0257 (10)	0.0263 (9)	0.0040 (7)	0.0053 (7)	0.0011 (8)
C9	0.0250 (10)	0.0284 (11)	0.0350 (11)	−0.0012 (8)	0.0064 (8)	−0.0031 (8)
C10	0.0247 (10)	0.0299 (11)	0.0340 (11)	0.0014 (8)	0.0074 (8)	−0.0014 (8)
C11	0.0238 (10)	0.0311 (11)	0.0345 (11)	0.0004 (8)	0.0063 (8)	−0.0026 (9)
C12	0.0236 (10)	0.0324 (11)	0.0353 (11)	0.0011 (8)	0.0067 (8)	−0.0013 (9)
C13	0.0253 (10)	0.0337 (12)	0.0347 (11)	0.0000 (8)	0.0079 (8)	−0.0023 (9)
C14	0.0256 (11)	0.0365 (12)	0.0344 (11)	0.0004 (9)	0.0075 (9)	−0.0005 (9)
C15	0.0271 (11)	0.0404 (13)	0.0388 (12)	−0.0014 (9)	0.0092 (9)	−0.0039 (10)
C16	0.0244 (11)	0.0546 (15)	0.0462 (14)	−0.0006 (10)	0.0069 (10)	−0.0003 (12)

Geometric parameters (Å, º) top

O1—C1	1.220 (3)	C10—H10A	0.9700
O2—C2	1.204 (3)	C10—H10B	0.9700
N1—C1	1.365 (3)	C11—C12	1.528 (3)
N1—C8	1.419 (3)	C11—H11A	0.9700
N1—C9	1.456 (3)	C11—H11B	0.9700
C1—C2	1.558 (3)	C12—C13	1.526 (3)
C2—C3	1.462 (3)	C12—H12A	0.9700
C3—C4	1.383 (3)	C12—H12B	0.9700
C3—C8	1.406 (3)	C13—C14	1.524 (3)
C4—C5	1.390 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.387 (3)	C14—C15	1.524 (3)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.398 (3)	C14—H14B	0.9700
C6—H6	0.9300	C15—C16	1.528 (3)
C7—C8	1.372 (3)	C15—H15A	0.9700
C7—H7	0.9300	C15—H15B	0.9700
C9—C10	1.524 (3)	C16—H16A	0.9600
C9—H9A	0.9700	C16—H16B	0.9600
C9—H9B	0.9700	C16—H16C	0.9600
C10—C11	1.526 (3)

C1—N1—C8	110.93 (17)	H10A—C10—H10B	107.8
C1—N1—C9	123.59 (18)	C10—C11—C12	112.44 (18)
C8—N1—C9	124.91 (17)	C10—C11—H11A	109.1
O1—C1—N1	126.7 (2)	C12—C11—H11A	109.1
O1—C1—C2	127.1 (2)	C10—C11—H11B	109.1
N1—C1—C2	106.24 (17)	C12—C11—H11B	109.1
O2—C2—C3	131.6 (2)	H11A—C11—H11B	107.8
O2—C2—C1	123.6 (2)	C13—C12—C11	113.79 (18)
C3—C2—C1	104.83 (16)	C13—C12—H12A	108.8
C4—C3—C8	120.78 (18)	C11—C12—H12A	108.8
C4—C3—C2	131.56 (19)	C13—C12—H12B	108.8
C8—C3—C2	107.65 (18)	C11—C12—H12B	108.8
C3—C4—C5	118.16 (19)	H12A—C12—H12B	107.7
C3—C4—H4	120.9	C14—C13—C12	113.04 (18)
C5—C4—H4	120.9	C14—C13—H13A	109.0
C6—C5—C4	120.4 (2)	C12—C13—H13A	109.0
C6—C5—H5	119.8	C14—C13—H13B	109.0
C4—C5—H5	119.8	C12—C13—H13B	109.0
C5—C6—C7	122.01 (19)	H13A—C13—H13B	107.8
C5—C6—H6	119.0	C13—C14—C15	113.60 (19)
C7—C6—H6	119.0	C13—C14—H14A	108.8
C8—C7—C6	117.09 (19)	C15—C14—H14A	108.8
C8—C7—H7	121.5	C13—C14—H14B	108.8
C6—C7—H7	121.5	C15—C14—H14B	108.8
C7—C8—C3	121.54 (19)	H14A—C14—H14B	107.7
C7—C8—N1	128.20 (18)	C14—C15—C16	112.6 (2)
C3—C8—N1	110.25 (17)	C14—C15—H15A	109.1
N1—C9—C10	112.20 (17)	C16—C15—H15A	109.1
N1—C9—H9A	109.2	C14—C15—H15B	109.1
C10—C9—H9A	109.2	C16—C15—H15B	109.1
N1—C9—H9B	109.2	H15A—C15—H15B	107.8
C10—C9—H9B	109.2	C15—C16—H16A	109.5
H9A—C9—H9B	107.9	C15—C16—H16B	109.5
C9—C10—C11	112.85 (17)	H16A—C16—H16B	109.5
C9—C10—H10A	109.0	C15—C16—H16C	109.5
C11—C10—H10A	109.0	H16A—C16—H16C	109.5
C9—C10—H10B	109.0	H16B—C16—H16C	109.5
C11—C10—H10B	109.0

C8—N1—C1—O1	−175.8 (2)	C6—C7—C8—N1	−179.05 (19)
C9—N1—C1—O1	−4.1 (3)	C4—C3—C8—C7	−0.5 (3)
C8—N1—C1—C2	3.3 (2)	C2—C3—C8—C7	−179.61 (18)
C9—N1—C1—C2	174.96 (17)	C4—C3—C8—N1	179.39 (18)
O1—C1—C2—O2	−2.5 (3)	C2—C3—C8—N1	0.3 (2)
N1—C1—C2—O2	178.42 (19)	C1—N1—C8—C7	177.49 (19)
O1—C1—C2—C3	176.1 (2)	C9—N1—C8—C7	5.9 (3)
N1—C1—C2—C3	−3.0 (2)	C1—N1—C8—C3	−2.4 (2)
O2—C2—C3—C4	1.1 (4)	C9—N1—C8—C3	−173.93 (18)
C1—C2—C3—C4	−177.4 (2)	C1—N1—C9—C10	−93.2 (2)
O2—C2—C3—C8	−180.0 (2)	C8—N1—C9—C10	77.3 (2)
C1—C2—C3—C8	1.6 (2)	N1—C9—C10—C11	172.83 (17)
C8—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	179.35 (18)
C2—C3—C4—C5	178.5 (2)	C10—C11—C12—C13	176.35 (18)
C3—C4—C5—C6	0.8 (3)	C11—C12—C13—C14	179.79 (18)
C4—C5—C6—C7	−0.5 (3)	C12—C13—C14—C15	178.69 (18)
C5—C6—C7—C8	−0.3 (3)	C13—C14—C15—C16	179.56 (19)
C6—C7—C8—C3	0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.49	3.156 (3)	129
C6—H6···O2ⁱⁱ	0.93	2.57	3.260 (3)	131
C4—H4···O2ⁱⁱⁱ	0.93	2.55	3.470 (3)	170

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.49	3.156 (3)	129.0
C6—H6···O2ⁱⁱ	0.93	2.57	3.260 (3)	131.0
C4—H4···O2ⁱⁱⁱ	0.93	2.55	3.470 (3)	170.2

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

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Volume 69| Part 12| December 2013| Page o1801

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