1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­yl]indoline-2,3-dione

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

doi:10.1107/S1600536814008423

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o588

doi:10.1107/S1600536814008423

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1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]indoline-2,3-dione

Fatima-Zahrae Qachchachi,^a ^* Youssef Kandri Rodi,^a El Mokhtar Essassi,^b Michael Bodensteiner ^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, ^cX-Ray Structure Analysis, University of Regensburg, D-93053 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 7 April 2014; accepted 14 April 2014; online 18 April 2014)

In the title compound, C₁₈H₁₄N₄O₂, the triazole ring makes dihedral angles of 77.32 (8) and 75.56 (9)°, respectively, with the indoline residue and the terminal phenyl group. In the crystal, molecules are linked by C—H⋯N hydrogen bonds into tapes parallel to the b axis. The tapes are linked together by π–π interactions between triazole rings [inter-centroid distance = 3.4945 (9) Å].

CCDC reference: 997252

Related literature

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010 ); Da Silva et al. (2001 ); Ramachandran (2011 ); Smitha et al. (2008 ). For structures of indoline-2,3-dione derivatives, see: Qachchachi et al. (2013 , 2014 ).

Experimental

Crystal data

C₁₈H₁₄N₄O₂
M_r = 318.33
Monoclinic, P 2₁ /c
a = 11.53860 (18) Å
b = 5.38700 (9) Å
c = 23.2433 (4) Å
β = 92.1048 (16)°
V = 1443.79 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 123 K
0.20 × 0.04 × 0.02 mm

Data collection

Agilent SuperNova, Single source at offset, Atlas diffractometer
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2013 ), using expressions derived from Clark & Reid (1995 )] T_min = 0.722, T_max = 1.000
11043 measured reflections
2882 independent reflections
2480 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.123
S = 1.04
2882 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.44 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
C11—H11⋯N2ⁱ	0.93	2.50	3.383 (2)	158
C11—H11⋯N3ⁱ	0.93	2.40	3.313 (2)	167
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2013); 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: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 997252

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814008423/bt6975sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008423/bt6975Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008423/bt6975Isup3.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; 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 (Qachchachi et al., 2013, 2014), we report in this paper the synthesis of a new indoline-2,3-dione derivative.

The molecule of title compound is build up from a fused five- and six-membered rings linked to a triazole ring which is connected to a benzyl ring as shown in Fig. 1. The indoline ring and the two carbonyl oxygen atoms are nearly coplanar, with the largest deviation from the mean plane being -0.059 (2) A° at O2 atom. The triazole plane is nearly perpendicular to the mean plane passing through the fused ring system (N1, C1 to C8) and to the terminal phenyl ring (C13 to C18) as indicated by the dihedral angles between them of 77.32 (8)° and 75.56 (9)°, respectively. The indazole system makes a dihedral angle of 77.02 (8)° with the phenyl ring.

In the crystal, the molecules are linked by C11–H11···N2 and C11–H11···N3 hydrogen bonds in the way to build bands parallel to the b axis direction. Two bands are linked together by π–π interactions between triazole rings [intercentroid distance = 3.494 Å] as shown in Fig. 2 and Table 1.

Related literature top

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010); Da Silva et al. (2001); Ramachandran (2011); Smitha et al. (2008). For structures of indoline-2,3-dione derivatives, see: Qachchachi et al. (2013, 2014).

Experimental top

To a solution of 1-(prop-2-ynyl)indoline-2,3-dione (0.2 g, 2.4 mmol) dissolved in EtOH/H₂O (1,1) was added 1-(azidomethyl)benzene (0.4 g, 4.1 mmol), in presence of CuSO₄. The mixture was stirred for 24 h; the reaction was 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 yellow crystals in 81% yield.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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 the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. : Intermolecular π–π (red dashed line) and hydrogen interactions (dashed blue lines) in the title compound.

1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]indoline-2,3-dione top

Crystal data top

C₁₈H₁₄N₄O₂	F(000) = 664
M_r = 318.33	D_x = 1.464 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4927 reflections
a = 11.53860 (18) Å	θ = 3.8–73.3°
b = 5.38700 (9) Å	µ = 0.81 mm⁻¹
c = 23.2433 (4) Å	T = 123 K
β = 92.1048 (16)°	Rod, clear intense yellow
V = 1443.79 (4) Å³	0.20 × 0.04 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova, Single source at offset, Atlas diffractometer	2882 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2480 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.3546 pixels mm^-1	θ_max = 73.5°, θ_min = 3.8°
ω scans	h = −14→11
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2013), using expressions derived from Clark & Reid (1995)]	k = −6→6
T_min = 0.722, T_max = 1.000	l = −28→27
11043 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0677P)² + 0.6175P] where P = (F_o² + 2F_c²)/3
2882 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₄N₄O₂	V = 1443.79 (4) Å³
M_r = 318.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.53860 (18) Å	µ = 0.81 mm⁻¹
b = 5.38700 (9) Å	T = 123 K
c = 23.2433 (4) Å	0.20 × 0.04 × 0.02 mm
β = 92.1048 (16)°

Data collection top

Agilent SuperNova, Single source at offset, Atlas diffractometer	2882 independent reflections
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2013), using expressions derived from Clark & Reid (1995)]	2480 reflections with I > 2σ(I)
T_min = 0.722, T_max = 1.000	R_int = 0.032
11043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	Δρ_max = 0.44 e Å⁻³
2882 reflections	Δρ_min = −0.22 e Å⁻³
217 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	0.65655 (11)	−0.1406 (2)	1.29231 (5)	0.0327 (3)
O2	0.48639 (10)	−0.1470 (2)	1.19284 (6)	0.0333 (3)
N1	0.59263 (12)	0.1979 (3)	1.16704 (6)	0.0258 (3)
N3	0.66397 (12)	−0.0542 (2)	0.99818 (6)	0.0267 (3)
N4	0.67538 (12)	0.1811 (3)	0.98001 (6)	0.0255 (3)
N2	0.61294 (12)	−0.0461 (3)	1.04795 (6)	0.0264 (3)
C9	0.52982 (14)	0.2675 (3)	1.11417 (7)	0.0269 (4)
H9A	0.5179	0.4457	1.1140	0.032*
H9B	0.4541	0.1888	1.1133	0.032*
C1	0.69237 (13)	0.3209 (3)	1.18873 (7)	0.0235 (3)
C2	0.74712 (14)	0.5253 (3)	1.16601 (7)	0.0253 (3)
H2	0.7192	0.6016	1.1324	0.030*
C4	0.88894 (14)	0.5000 (3)	1.24613 (7)	0.0287 (4)
H4	0.9552	0.5625	1.2649	0.034*
C10	0.59134 (13)	0.1956 (3)	1.06114 (7)	0.0242 (3)
C18	0.94153 (15)	0.2600 (3)	0.94699 (7)	0.0287 (4)
H18	0.9284	0.4072	0.9666	0.034*
C6	0.73451 (14)	0.2077 (3)	1.23951 (7)	0.0250 (3)
C5	0.83290 (14)	0.2949 (3)	1.26844 (7)	0.0276 (4)
H5	0.8610	0.2184	1.3020	0.033*
C13	0.84837 (15)	0.1331 (3)	0.92142 (7)	0.0267 (4)
C3	0.84634 (14)	0.6118 (3)	1.19591 (7)	0.0274 (4)
H3	0.8851	0.7488	1.1817	0.033*
C7	0.65586 (14)	0.0030 (3)	1.25238 (7)	0.0264 (4)
C12	0.72714 (15)	0.2352 (3)	0.92448 (7)	0.0293 (4)
H12A	0.7291	0.4135	0.9188	0.035*
H12B	0.6789	0.1639	0.8937	0.035*
C17	1.05397 (15)	0.1708 (4)	0.94380 (8)	0.0332 (4)
H17	1.1155	0.2578	0.9611	0.040*
C16	1.07402 (17)	−0.0482 (4)	0.91471 (8)	0.0356 (4)
H16	1.1491	−0.1094	0.9125	0.043*
C11	0.63147 (13)	0.3411 (3)	1.01791 (7)	0.0258 (3)
H11	0.6289	0.5133	1.0153	0.031*
C14	0.86952 (17)	−0.0866 (3)	0.89222 (7)	0.0327 (4)
H14	0.8082	−0.1740	0.8748	0.039*
C15	0.98220 (18)	−0.1757 (4)	0.88899 (8)	0.0376 (4)
H15	0.9958	−0.3225	0.8693	0.045*
C8	0.56440 (14)	0.0017 (3)	1.20128 (7)	0.0268 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0334 (6)	0.0294 (6)	0.0359 (7)	0.0032 (5)	0.0104 (5)	0.0061 (5)
O2	0.0274 (6)	0.0285 (6)	0.0444 (7)	−0.0058 (5)	0.0064 (5)	−0.0018 (5)
N1	0.0235 (6)	0.0253 (7)	0.0286 (7)	−0.0017 (5)	0.0023 (5)	−0.0016 (5)
N3	0.0303 (7)	0.0193 (7)	0.0307 (7)	−0.0013 (5)	0.0024 (6)	0.0006 (5)
N4	0.0250 (7)	0.0215 (7)	0.0300 (7)	−0.0017 (5)	−0.0001 (5)	0.0026 (5)
N2	0.0275 (7)	0.0220 (7)	0.0299 (7)	−0.0005 (5)	0.0026 (5)	0.0003 (5)
C9	0.0239 (7)	0.0259 (8)	0.0307 (8)	0.0012 (6)	0.0000 (6)	−0.0031 (6)
C1	0.0223 (7)	0.0236 (8)	0.0250 (7)	0.0021 (6)	0.0054 (6)	−0.0039 (6)
C2	0.0269 (8)	0.0234 (8)	0.0259 (8)	0.0001 (6)	0.0040 (6)	−0.0015 (6)
C4	0.0254 (8)	0.0318 (9)	0.0288 (8)	−0.0024 (7)	0.0018 (6)	−0.0049 (7)
C10	0.0201 (7)	0.0225 (8)	0.0298 (8)	0.0008 (6)	−0.0027 (6)	−0.0019 (6)
C18	0.0337 (9)	0.0257 (8)	0.0267 (8)	−0.0003 (7)	0.0032 (7)	−0.0006 (6)
C6	0.0256 (7)	0.0242 (8)	0.0256 (8)	0.0027 (6)	0.0076 (6)	−0.0017 (6)
C5	0.0270 (8)	0.0306 (8)	0.0255 (8)	0.0032 (6)	0.0039 (6)	−0.0014 (6)
C13	0.0323 (8)	0.0242 (8)	0.0238 (7)	−0.0008 (6)	0.0033 (6)	0.0061 (6)
C3	0.0267 (8)	0.0256 (8)	0.0303 (8)	−0.0030 (6)	0.0075 (6)	−0.0025 (6)
C7	0.0267 (8)	0.0219 (8)	0.0310 (8)	0.0030 (6)	0.0090 (6)	−0.0011 (6)
C12	0.0320 (8)	0.0292 (9)	0.0268 (8)	−0.0017 (7)	0.0010 (6)	0.0056 (7)
C17	0.0304 (9)	0.0377 (10)	0.0315 (9)	−0.0009 (7)	0.0032 (7)	0.0051 (7)
C16	0.0377 (9)	0.0379 (10)	0.0318 (9)	0.0098 (8)	0.0108 (7)	0.0092 (8)
C11	0.0239 (8)	0.0190 (7)	0.0343 (9)	0.0004 (6)	−0.0029 (6)	−0.0008 (6)
C14	0.0430 (10)	0.0266 (9)	0.0284 (8)	−0.0052 (7)	0.0022 (7)	0.0005 (7)
C15	0.0555 (12)	0.0277 (9)	0.0305 (9)	0.0063 (8)	0.0130 (8)	0.0023 (7)
C8	0.0238 (8)	0.0227 (8)	0.0343 (9)	0.0001 (6)	0.0081 (6)	−0.0024 (6)

Geometric parameters (Å, º) top

O1—C7	1.208 (2)	C18—C17	1.388 (3)
O2—C8	1.216 (2)	C18—C13	1.389 (2)
N1—C8	1.370 (2)	C18—H18	0.9300
N1—C1	1.406 (2)	C6—C5	1.380 (2)
N1—C9	1.453 (2)	C6—C7	1.466 (2)
N3—N2	1.318 (2)	C5—H5	0.9300
N3—N4	1.3436 (19)	C13—C14	1.390 (2)
N4—C11	1.345 (2)	C13—C12	1.507 (2)
N4—C12	1.471 (2)	C3—H3	0.9300
N2—C10	1.362 (2)	C7—C8	1.560 (2)
C9—C10	1.496 (2)	C12—H12A	0.9700
C9—H9A	0.9700	C12—H12B	0.9700
C9—H9B	0.9700	C17—C16	1.383 (3)
C1—C2	1.384 (2)	C17—H17	0.9300
C1—C6	1.400 (2)	C16—C15	1.380 (3)
C2—C3	1.397 (2)	C16—H16	0.9300
C2—H2	0.9300	C11—H11	0.9300
C4—C3	1.387 (2)	C14—C15	1.391 (3)
C4—C5	1.390 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C10—C11	1.369 (2)

C8—N1—C1	111.37 (14)	C4—C5—H5	120.8
C8—N1—C9	124.67 (14)	C18—C13—C14	118.74 (16)
C1—N1—C9	123.94 (14)	C18—C13—C12	120.34 (16)
N2—N3—N4	107.26 (13)	C14—C13—C12	120.91 (16)
N3—N4—C11	110.80 (13)	C4—C3—C2	122.16 (16)
N3—N4—C12	120.69 (14)	C4—C3—H3	118.9
C11—N4—C12	128.48 (14)	C2—C3—H3	118.9
N3—N2—C10	108.69 (13)	O1—C7—C6	130.68 (17)
N1—C9—C10	113.14 (13)	O1—C7—C8	124.58 (15)
N1—C9—H9A	109.0	C6—C7—C8	104.74 (13)
C10—C9—H9A	109.0	N4—C12—C13	112.11 (13)
N1—C9—H9B	109.0	N4—C12—H12A	109.2
C10—C9—H9B	109.0	C13—C12—H12A	109.2
H9A—C9—H9B	107.8	N4—C12—H12B	109.2
C2—C1—C6	121.28 (15)	C13—C12—H12B	109.2
C2—C1—N1	128.14 (15)	H12A—C12—H12B	107.9
C6—C1—N1	110.58 (14)	C16—C17—C18	119.66 (18)
C1—C2—C3	116.92 (15)	C16—C17—H17	120.2
C1—C2—H2	121.5	C18—C17—H17	120.2
C3—C2—H2	121.5	C15—C16—C17	119.75 (17)
C3—C4—C5	120.24 (16)	C15—C16—H16	120.1
C3—C4—H4	119.9	C17—C16—H16	120.1
C5—C4—H4	119.9	N4—C11—C10	105.03 (14)
N2—C10—C11	108.21 (14)	N4—C11—H11	127.5
N2—C10—C9	121.95 (15)	C10—C11—H11	127.5
C11—C10—C9	129.80 (15)	C13—C14—C15	120.10 (17)
C17—C18—C13	121.12 (17)	C13—C14—H14	120.0
C17—C18—H18	119.4	C15—C14—H14	120.0
C13—C18—H18	119.4	C16—C15—C14	120.62 (17)
C5—C6—C1	121.09 (16)	C16—C15—H15	119.7
C5—C6—C7	131.36 (16)	C14—C15—H15	119.7
C1—C6—C7	107.54 (15)	O2—C8—N1	127.25 (16)
C6—C5—C4	118.32 (16)	O2—C8—C7	127.03 (16)
C6—C5—H5	120.8	N1—C8—C7	105.70 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N2ⁱ	0.93	2.50	3.383 (2)	158
C11—H11···N3ⁱ	0.93	2.40	3.313 (2)	167

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N2ⁱ	0.93	2.50	3.383 (2)	158.4
C11—H11···N3ⁱ	0.93	2.40	3.313 (2)	166.9

Symmetry code: (i) x, y+1, z.

References

Agilent, (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England. Google Scholar
Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M. S. & Ahsan, W. (2010). Int. J. Pharm. Sci. Drug Res. 2, 229–235. CAS Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Da Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273–324. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Qachchachi, F.-Z., Kandri Rodi, Y., Essassi, E. M., Bodensteiner, M. & El Ammari, L. (2014). Acta Cryst. E70, o361–o362. CSD CrossRef CAS IUCr Journals Google Scholar
Qachchachi, F.-Z., Kandri Rodi, Y., Essassi, E. M., Kunz, W. & El Ammari, L. (2013). Acta Cryst. E69, o1801. CSD CrossRef IUCr Journals Google Scholar
Ramachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289–294. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smitha, S., Pandeya, S. N., Stables, J. P. & Ganapathy, S. (2008). Sci. Pharm. 76, 621–636. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 5| May 2014| Page o588

doi:10.1107/S1600536814008423

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