1-(1-Nonyl-2-oxoindolin-3-yl­idene)thio­semicarbazide

Mamari, K.; Zerzouf, A.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S160053681001651X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1332

https://doi.org/10.1107/S160053681001651X

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1-(1-Nonyl-2-oxoindolin-3-ylidene)thiosemicarbazide

Khalil Mamari,^a Abdelfettah Zerzouf,^b Hafid Zouihri,^c El Mokhtar Essassi ^a and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bLaboratoire de Chimie Organique et Etudes Physicochimiques, ENS Rabat, Morocco, ^cCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, 0000 Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 May 2010; accepted 5 May 2010; online 15 May 2010)

In the title compound, C₁₈H₂₆N₄OS, the imine C=N bond has a Z configuration, whereas the N—N—C=S unit has an E conformation. In the crystal, molecules are connected through N—H⋯O hydrogen bonds, forming zigzag chains running along the b axis. The nonyl chain adopts an extended zigzag conformation.

Related literature

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008 ).

Experimental

Crystal data

C₁₈H₂₆N₄OS
M_r = 346.49
Monoclinic, P 2₁ /n
a = 11.5343 (2) Å
b = 10.5921 (2) Å
c = 15.6262 (3) Å
β = 95.922 (1)°
V = 1898.90 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 180 K
0.17 × 0.15 × 0.09 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.984
26603 measured reflections
5510 independent reflections
4006 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.134
S = 1.09
5510 reflections
229 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H12⋯O1ⁱ	0.86 (1)	2.22 (1)	3.002 (2)	152 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001651X/bt5264sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001651X/bt5264Isup2.hkl

checkCIF report

Comment top

N-Substituted isatins (Bouhfid et al., 2008) represent a large family of heterocyclic compounds reported to show a wide range of useful medicinal properties. These condense readily with thiosemicarbazides to form crystalline thiosemicarbazones. The title 1-nonylisatin derivative has a Z configuration around the imine C=N bond and E conformation about the C(=S)–NH₂ bond (Scheme I, Fig. 1). The molecules are connected to zigzag chains though N–H···O hydrogen bonds along the b-axis of the monoclinic unit cell (Fig. 2). The nonyl chain adopts a nearly regular zigzag conformation; however, the rigid nature gives rises to voids in the crystal.

Related literature top

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).

Experimental top

1-Nonyl-isatin (1 g ,3 mmol) and thiosemicarbazide (0.27 g ,3 mmol) were dissolved in aqueous ethanol (50 ml); a few drops of glacial acetic acid were added. The mixture was heated for 4 hours. Yellow crystals separated from the cool solution in 80% yield.

Structure description top

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C₁₈H₂₆N₄OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded helical chain motif.

1-(1-Nonyl-2-oxoindolin-3-ylidene)thiosemicarbazide top

Crystal data top

C₁₈H₂₆N₄OS	F(000) = 744
M_r = 346.49	D_x = 1.212 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6721 reflections
a = 11.5343 (2) Å	θ = 2.6–29.8°
b = 10.5921 (2) Å	µ = 0.18 mm⁻¹
c = 15.6262 (3) Å	T = 180 K
β = 95.922 (1)°	Prism, yellow
V = 1898.90 (6) Å³	0.17 × 0.15 × 0.09 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	5510 independent reflections
Radiation source: fine-focus sealed tube	4006 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 30.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.970, T_max = 0.984	k = −14→14
26603 measured reflections	l = −21→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0722P)² + 0.1904P] where P = (F_o² + 2F_c²)/3
5510 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.48 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₈H₂₆N₄OS	V = 1898.90 (6) Å³
M_r = 346.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5343 (2) Å	µ = 0.18 mm⁻¹
b = 10.5921 (2) Å	T = 180 K
c = 15.6262 (3) Å	0.17 × 0.15 × 0.09 mm
β = 95.922 (1)°

Data collection top

Bruker X8 APEXII diffractometer	5510 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4006 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.984	R_int = 0.041
26603 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.48 e Å⁻³
5510 reflections	Δρ_min = −0.51 e Å⁻³
229 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.76947 (4)	0.88269 (3)	0.65446 (2)	0.02943 (12)
O1	0.86020 (10)	0.77068 (9)	0.93146 (7)	0.0283 (2)
N1	0.73497 (14)	1.11116 (12)	0.71834 (9)	0.0314 (3)
N2	0.78603 (11)	0.95357 (11)	0.81532 (8)	0.0230 (3)
N3	0.79185 (10)	1.03853 (11)	0.88032 (7)	0.0213 (2)
N4	0.90309 (11)	0.86435 (11)	1.06470 (8)	0.0240 (3)
C1	0.76202 (13)	0.99075 (13)	0.73160 (9)	0.0221 (3)
C2	0.82742 (12)	0.99591 (12)	0.95604 (9)	0.0205 (3)
C3	0.84765 (12)	1.07018 (14)	1.03435 (9)	0.0224 (3)
C4	0.83255 (13)	1.19707 (14)	1.05261 (10)	0.0276 (3)
H4	0.8005	1.2539	1.0095	0.033*
C5	0.86590 (15)	1.23851 (16)	1.13619 (11)	0.0350 (4)
H5	0.8562	1.3248	1.1503	0.042*
C6	0.91290 (15)	1.15564 (17)	1.19886 (11)	0.0360 (4)
H6	0.9352	1.1865	1.2553	0.043*
C7	0.92842 (14)	1.02816 (16)	1.18136 (10)	0.0304 (3)
H7	0.9605	0.9716	1.2247	0.037*
C8	0.89532 (12)	0.98741 (14)	1.09875 (9)	0.0237 (3)
C9	0.86411 (12)	0.86286 (13)	0.97964 (9)	0.0221 (3)
C10	0.95911 (14)	0.75743 (14)	1.11096 (10)	0.0283 (3)
H10A	1.0326	0.7868	1.1432	0.034*
H10B	0.9797	0.6939	1.0686	0.034*
C11	0.88473 (13)	0.69389 (14)	1.17376 (10)	0.0275 (3)
H11A	0.8186	0.6493	1.1415	0.033*
H11B	0.8527	0.7585	1.2106	0.033*
C12	0.95880 (13)	0.60010 (14)	1.22971 (10)	0.0281 (3)
H12A	0.9906	0.5368	1.1918	0.034*
H12B	1.0256	0.6459	1.2601	0.034*
C13	0.89450 (13)	0.53100 (14)	1.29607 (9)	0.0260 (3)
H13A	0.8586	0.5936	1.3323	0.031*
H13B	0.8312	0.4795	1.2661	0.031*
C14	0.97559 (13)	0.44591 (14)	1.35311 (10)	0.0265 (3)
H14A	1.0372	0.4986	1.3841	0.032*
H14B	1.0140	0.3865	1.3161	0.032*
C15	0.91596 (13)	0.36994 (14)	1.41887 (10)	0.0273 (3)
H15A	0.8789	0.4290	1.4570	0.033*
H15B	0.8536	0.3179	1.3883	0.033*
C16	0.99913 (14)	0.28424 (14)	1.47370 (10)	0.0289 (3)
H16A	1.0606	0.3368	1.5050	0.035*
H16B	1.0374	0.2268	1.4353	0.035*
C17	0.94113 (16)	0.20532 (16)	1.53871 (11)	0.0360 (4)
H17A	0.8791	0.1531	1.5078	0.043*
H17B	0.9040	0.2624	1.5780	0.043*
C18	1.0270 (2)	0.11952 (18)	1.59148 (13)	0.0487 (5)
H18A	0.9857	0.0709	1.6322	0.073*
H18B	1.0877	0.1709	1.6232	0.073*
H18C	1.0628	0.0616	1.5530	0.073*
H11	0.7307 (17)	1.1607 (16)	0.7620 (9)	0.043 (5)*
H12	0.7173 (18)	1.1345 (19)	0.6657 (7)	0.050 (6)*
H2	0.8141 (15)	0.8786 (11)	0.8267 (12)	0.036 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0426 (2)	0.02504 (19)	0.02068 (19)	−0.00110 (15)	0.00317 (16)	−0.00439 (13)
O1	0.0369 (6)	0.0213 (5)	0.0260 (6)	−0.0001 (4)	0.0002 (5)	−0.0006 (4)
N1	0.0521 (9)	0.0226 (6)	0.0189 (6)	0.0049 (6)	0.0001 (6)	0.0012 (5)
N2	0.0315 (7)	0.0189 (6)	0.0177 (6)	0.0004 (5)	−0.0013 (5)	−0.0006 (4)
N3	0.0246 (6)	0.0207 (5)	0.0183 (6)	−0.0014 (4)	0.0014 (5)	−0.0005 (4)
N4	0.0269 (6)	0.0258 (6)	0.0189 (6)	0.0009 (5)	0.0005 (5)	0.0040 (4)
C1	0.0254 (7)	0.0213 (6)	0.0192 (7)	−0.0022 (5)	0.0011 (5)	0.0009 (5)
C2	0.0221 (7)	0.0205 (6)	0.0190 (7)	−0.0012 (5)	0.0023 (5)	0.0006 (5)
C3	0.0232 (7)	0.0263 (7)	0.0177 (6)	−0.0021 (5)	0.0022 (5)	−0.0004 (5)
C4	0.0314 (8)	0.0264 (7)	0.0252 (7)	−0.0015 (6)	0.0031 (6)	−0.0029 (6)
C5	0.0416 (9)	0.0334 (8)	0.0304 (9)	−0.0051 (7)	0.0060 (7)	−0.0108 (6)
C6	0.0385 (9)	0.0475 (10)	0.0217 (8)	−0.0080 (7)	0.0020 (7)	−0.0104 (7)
C7	0.0301 (8)	0.0400 (9)	0.0207 (7)	−0.0038 (6)	0.0001 (6)	0.0011 (6)
C8	0.0224 (7)	0.0283 (7)	0.0205 (7)	−0.0033 (5)	0.0026 (5)	0.0005 (5)
C9	0.0228 (7)	0.0232 (6)	0.0202 (7)	−0.0022 (5)	0.0013 (5)	0.0033 (5)
C10	0.0287 (8)	0.0303 (7)	0.0256 (8)	0.0039 (6)	0.0019 (6)	0.0090 (6)
C11	0.0277 (8)	0.0293 (7)	0.0253 (7)	0.0007 (6)	0.0016 (6)	0.0084 (6)
C12	0.0280 (8)	0.0306 (7)	0.0255 (8)	0.0026 (6)	0.0025 (6)	0.0086 (6)
C13	0.0273 (7)	0.0275 (7)	0.0234 (7)	0.0012 (6)	0.0030 (6)	0.0037 (5)
C14	0.0273 (7)	0.0276 (7)	0.0248 (7)	0.0014 (6)	0.0040 (6)	0.0055 (6)
C15	0.0288 (8)	0.0276 (7)	0.0261 (7)	−0.0001 (6)	0.0061 (6)	0.0051 (6)
C16	0.0330 (8)	0.0279 (7)	0.0263 (8)	0.0014 (6)	0.0057 (6)	0.0061 (6)
C17	0.0444 (10)	0.0335 (8)	0.0298 (8)	−0.0051 (7)	0.0029 (7)	0.0092 (7)
C18	0.0659 (13)	0.0398 (10)	0.0372 (10)	−0.0097 (9)	−0.0100 (9)	0.0145 (8)

Geometric parameters (Å, º) top

S1—C1	1.6710 (14)	C10—H10B	0.9900
O1—C9	1.2309 (17)	C11—C12	1.525 (2)
N1—C1	1.3242 (19)	C11—H11A	0.9900
N1—H11	0.866 (9)	C11—H11B	0.9900
N1—H12	0.862 (9)	C12—C13	1.523 (2)
N2—N3	1.3534 (16)	C12—H12A	0.9900
N2—C1	1.3669 (18)	C12—H12B	0.9900
N2—H2	0.869 (9)	C13—C14	1.520 (2)
N3—C2	1.2931 (17)	C13—H13A	0.9900
N4—C9	1.3585 (18)	C13—H13B	0.9900
N4—C8	1.4142 (18)	C14—C15	1.524 (2)
N4—C10	1.4582 (18)	C14—H14A	0.9900
C2—C3	1.4532 (19)	C14—H14B	0.9900
C2—C9	1.5063 (19)	C15—C16	1.519 (2)
C3—C4	1.389 (2)	C15—H15A	0.9900
C3—C8	1.403 (2)	C15—H15B	0.9900
C4—C5	1.394 (2)	C16—C17	1.523 (2)
C4—H4	0.9500	C16—H16A	0.9900
C5—C6	1.384 (3)	C16—H16B	0.9900
C5—H5	0.9500	C17—C18	1.522 (3)
C6—C7	1.393 (2)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C7—C8	1.377 (2)	C18—H18A	0.9800
C7—H7	0.9500	C18—H18B	0.9800
C10—C11	1.525 (2)	C18—H18C	0.9800
C10—H10A	0.9900

C1—N1—H11	119.5 (14)	C10—C11—H11B	109.7
C1—N1—H12	117.0 (14)	C12—C11—H11B	109.7
H11—N1—H12	123.4 (19)	H11A—C11—H11B	108.2
N3—N2—C1	121.07 (11)	C13—C12—C11	114.83 (13)
N3—N2—H2	117.7 (13)	C13—C12—H12A	108.6
C1—N2—H2	119.6 (13)	C11—C12—H12A	108.6
C2—N3—N2	116.17 (11)	C13—C12—H12B	108.6
C9—N4—C8	110.57 (11)	C11—C12—H12B	108.6
C9—N4—C10	124.13 (12)	H12A—C12—H12B	107.5
C8—N4—C10	124.85 (12)	C14—C13—C12	111.77 (13)
N1—C1—N2	116.64 (13)	C14—C13—H13A	109.3
N1—C1—S1	125.15 (11)	C12—C13—H13A	109.3
N2—C1—S1	118.21 (10)	C14—C13—H13B	109.3
N3—C2—C3	126.14 (12)	C12—C13—H13B	109.3
N3—C2—C9	127.25 (12)	H13A—C13—H13B	107.9
C3—C2—C9	106.48 (12)	C13—C14—C15	114.55 (13)
C4—C3—C8	120.37 (13)	C13—C14—H14A	108.6
C4—C3—C2	133.18 (13)	C15—C14—H14A	108.6
C8—C3—C2	106.41 (12)	C13—C14—H14B	108.6
C3—C4—C5	117.97 (15)	C15—C14—H14B	108.6
C3—C4—H4	121.0	H14A—C14—H14B	107.6
C5—C4—H4	121.0	C16—C15—C14	113.15 (13)
C6—C5—C4	120.90 (15)	C16—C15—H15A	108.9
C6—C5—H5	119.6	C14—C15—H15A	108.9
C4—C5—H5	119.5	C16—C15—H15B	108.9
C5—C6—C7	121.67 (15)	C14—C15—H15B	108.9
C5—C6—H6	119.2	H15A—C15—H15B	107.8
C7—C6—H6	119.2	C15—C16—C17	114.13 (13)
C8—C7—C6	117.33 (15)	C15—C16—H16A	108.7
C8—C7—H7	121.3	C17—C16—H16A	108.7
C6—C7—H7	121.3	C15—C16—H16B	108.7
C7—C8—C3	121.77 (14)	C17—C16—H16B	108.7
C7—C8—N4	128.26 (14)	H16A—C16—H16B	107.6
C3—C8—N4	109.97 (12)	C16—C17—C18	112.53 (15)
O1—C9—N4	126.53 (13)	C16—C17—H17A	109.1
O1—C9—C2	126.92 (13)	C18—C17—H17A	109.1
N4—C9—C2	106.55 (12)	C16—C17—H17B	109.1
N4—C10—C11	114.32 (13)	C18—C17—H17B	109.1
N4—C10—H10A	108.7	H17A—C17—H17B	107.8
C11—C10—H10A	108.7	C17—C18—H18A	109.5
N4—C10—H10B	108.7	C17—C18—H18B	109.5
C11—C10—H10B	108.7	H18A—C18—H18B	109.5
H10A—C10—H10B	107.6	C17—C18—H18C	109.5
C10—C11—C12	109.71 (13)	H18A—C18—H18C	109.5
C10—C11—H11A	109.7	H18B—C18—H18C	109.5
C12—C11—H11A	109.7

C1—N2—N3—C2	−172.75 (13)	C10—N4—C8—C7	−5.9 (2)
N3—N2—C1—N1	−5.7 (2)	C9—N4—C8—C3	1.03 (17)
N3—N2—C1—S1	173.97 (10)	C10—N4—C8—C3	173.50 (13)
N2—N3—C2—C3	175.91 (13)	C8—N4—C9—O1	179.53 (14)
N2—N3—C2—C9	0.7 (2)	C10—N4—C9—O1	7.0 (2)
N3—C2—C3—C4	2.9 (3)	C8—N4—C9—C2	−0.18 (16)
C9—C2—C3—C4	178.91 (16)	C10—N4—C9—C2	−172.71 (13)
N3—C2—C3—C8	−174.78 (14)	N3—C2—C9—O1	−4.4 (2)
C9—C2—C3—C8	1.27 (15)	C3—C2—C9—O1	179.61 (14)
C8—C3—C4—C5	−0.1 (2)	N3—C2—C9—N4	175.31 (14)
C2—C3—C4—C5	−177.47 (15)	C3—C2—C9—N4	−0.69 (15)
C3—C4—C5—C6	0.2 (2)	C9—N4—C10—C11	−108.71 (16)
C4—C5—C6—C7	−0.2 (3)	C8—N4—C10—C11	79.81 (18)
C5—C6—C7—C8	0.2 (2)	N4—C10—C11—C12	−169.81 (13)
C6—C7—C8—C3	−0.1 (2)	C10—C11—C12—C13	179.42 (13)
C6—C7—C8—N4	179.29 (15)	C11—C12—C13—C14	−176.25 (13)
C4—C3—C8—C7	0.1 (2)	C12—C13—C14—C15	−177.78 (13)
C2—C3—C8—C7	178.06 (14)	C13—C14—C15—C16	178.98 (13)
C4—C3—C8—N4	−179.43 (13)	C14—C15—C16—C17	−178.83 (13)
C2—C3—C8—N4	−1.42 (16)	C15—C16—C17—C18	179.22 (15)
C9—N4—C8—C7	−178.41 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···S1ⁱ	0.87 (1)	2.69 (1)	3.499 (1)	156 (2)
N1—H12···O1ⁱ	0.86 (1)	2.22 (1)	3.002 (2)	152 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₆N₄OS
M_r	346.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	180
a, b, c (Å)	11.5343 (2), 10.5921 (2), 15.6262 (3)
β (°)	95.922 (1)
V (Å³)	1898.90 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.17 × 0.15 × 0.09

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	26603, 5510, 4006
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.134, 1.09
No. of reflections	5510
No. of parameters	229
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.51

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O1ⁱ	0.86 (1)	2.22 (1)	3.002 (2)	152 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Acknowledgements

We thank the Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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