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

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

doi:10.1107/S1600536810016521

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1333

https://doi.org/10.1107/S1600536810016521

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1-(1-Decyl-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, 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 1-alkylisatin 3-thiosemicarbazone, C₁₉H₂₈N₄OS, 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 by N—H⋯O hydrogen bonds, forming zigzag chains running along the b axis.

Related literature

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

Experimental

Crystal data

C₁₉H₂₈N₄OS
M_r = 360.51
Monoclinic, P 2₁ /n
a = 11.8856 (2) Å
b = 11.0055 (2) Å
c = 15.1638 (3) Å
β = 99.468 (1)°
V = 1956.51 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 180 K
0.23 × 0.14 × 0.12 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.979
26304 measured reflections
5715 independent reflections
4227 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.135
S = 1.06
5715 reflections
238 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O1ⁱ	0.86 (1)	2.19 (1)	2.986 (2)	154 (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/S1600536810016521/bt5265sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016521/bt5265Isup2.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-decylisatin derivative has a Z configuration around the imine C=N bond and E configuration the C(=S)–NH₂ bond (Scheme I, Fig. 1). The molecules form zigzag chains though N–H···O hydrogen bonds along the b-axis of the monoclinic unit cell (Fig. 2). The decyl chain adopts an irregular zigzag conformation; the irregular nature lead to a compact packing and there are no voids in the crystal.

Related literature top

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

Experimental top

1-Decyl-isatin (1 g, 3.1 mmol) and thiosemicarbazide (0.31 g, 3.4 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the molecule of C₁₉H₂₈N₄OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Packinig diagram of the title compound with hydrogen bonds drawn as dashed lines.

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

Crystal data top

C₁₉H₂₈N₄OS	F(000) = 776
M_r = 360.51	D_x = 1.224 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5658 reflections
a = 11.8856 (2) Å	θ = 2.3–28.7°
b = 11.0055 (2) Å	µ = 0.18 mm⁻¹
c = 15.1638 (3) Å	T = 180 K
β = 99.468 (1)°	Prism, yellow
V = 1956.51 (6) Å³	0.23 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	5715 independent reflections
Radiation source: fine-focus sealed tube	4227 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.960, T_max = 0.979	k = −13→15
26304 measured reflections	l = −18→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0721P)² + 0.276P] where P = (F_o² + 2F_c²)/3
5715 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₂₈N₄OS	V = 1956.51 (6) Å³
M_r = 360.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8856 (2) Å	µ = 0.18 mm⁻¹
b = 11.0055 (2) Å	T = 180 K
c = 15.1638 (3) Å	0.23 × 0.14 × 0.12 mm
β = 99.468 (1)°

Data collection top

Bruker X8 APEXII diffractometer	5715 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4227 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.979	R_int = 0.043
26304 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	3 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.30 e Å⁻³
5715 reflections	Δρ_min = −0.36 e Å⁻³
238 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.80459 (3)	0.78130 (4)	0.66953 (3)	0.03232 (12)
O1	0.66844 (10)	0.67702 (9)	0.91795 (7)	0.0330 (3)
N1	0.78312 (11)	1.00870 (12)	0.72565 (9)	0.0304 (3)
N2	0.73941 (11)	0.85612 (11)	0.81634 (8)	0.0277 (3)
N3	0.71786 (10)	0.93926 (10)	0.87721 (8)	0.0241 (2)
N4	0.61721 (10)	0.76378 (10)	1.04405 (8)	0.0232 (2)
C1	0.77480 (11)	0.89065 (12)	0.73872 (9)	0.0240 (3)
C2	0.68081 (11)	0.89632 (12)	0.94641 (9)	0.0221 (3)
C3	0.65089 (11)	0.96609 (12)	1.02047 (9)	0.0214 (3)
C4	0.65109 (12)	1.08920 (12)	1.03890 (10)	0.0250 (3)
H4	0.6761	1.1465	0.9994	0.030*
C5	0.61370 (12)	1.12684 (13)	1.11687 (10)	0.0289 (3)
H5	0.6136	1.2109	1.1310	0.035*
C6	0.57670 (12)	1.04303 (14)	1.17397 (10)	0.0296 (3)
H6	0.5518	1.0710	1.2268	0.035*
C7	0.57503 (12)	0.91890 (13)	1.15612 (9)	0.0266 (3)
H7	0.5491	0.8618	1.1953	0.032*
C8	0.61282 (11)	0.88257 (11)	1.07871 (9)	0.0214 (3)
C9	0.65662 (12)	0.76577 (12)	0.96510 (9)	0.0240 (3)
C10	0.58378 (12)	0.65187 (12)	1.08470 (10)	0.0258 (3)
H10A	0.5452	0.5974	1.0372	0.031*
H10B	0.5286	0.6716	1.1249	0.031*
C11	0.68480 (13)	0.58614 (14)	1.13747 (11)	0.0329 (3)
H11A	0.7232	0.6404	1.1852	0.040*
H11B	0.7402	0.5667	1.0974	0.040*
C12	0.64970 (14)	0.46857 (13)	1.17964 (11)	0.0319 (3)
H12A	0.5931	0.4257	1.1352	0.038*
H12B	0.7175	0.4154	1.1935	0.038*
C13	0.59920 (13)	0.48675 (12)	1.26434 (11)	0.0305 (3)
H13A	0.5286	0.5355	1.2500	0.037*
H13B	0.6539	0.5334	1.3079	0.037*
C14	0.57148 (13)	0.36767 (13)	1.30730 (11)	0.0314 (3)
H14A	0.6407	0.3161	1.3168	0.038*
H14B	0.5121	0.3243	1.2655	0.038*
C15	0.52981 (13)	0.38398 (14)	1.39615 (11)	0.0321 (3)
H15A	0.5876	0.4308	1.4369	0.039*
H15B	0.4588	0.4326	1.3860	0.039*
C16	0.50680 (14)	0.26574 (14)	1.44180 (11)	0.0341 (3)
H16A	0.5792	0.2204	1.4577	0.041*
H16B	0.4540	0.2153	1.3996	0.041*
C17	0.45517 (16)	0.28689 (16)	1.52591 (13)	0.0431 (4)
H17A	0.3889	0.3420	1.5111	0.052*
H17B	0.5123	0.3286	1.5706	0.052*
C18	0.41613 (17)	0.17156 (19)	1.56828 (14)	0.0511 (5)
H18A	0.3704	0.1947	1.6146	0.061*
H18B	0.3663	0.1242	1.5219	0.061*
C19	0.5135 (2)	0.09282 (19)	1.60994 (14)	0.0567 (5)
H19A	0.4836	0.0208	1.6363	0.085*
H19B	0.5625	0.1386	1.6567	0.085*
H19C	0.5579	0.0676	1.5641	0.085*
H11	0.8010 (16)	1.0349 (19)	0.6760 (9)	0.048 (6)*
H12	0.7606 (16)	1.0593 (15)	0.7628 (11)	0.044 (5)*
H2	0.7284 (16)	0.7811 (10)	0.8277 (13)	0.044 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0421 (2)	0.0309 (2)	0.0277 (2)	0.00066 (15)	0.01700 (16)	−0.00417 (15)
O1	0.0523 (7)	0.0207 (5)	0.0300 (6)	0.0001 (4)	0.0186 (5)	−0.0034 (4)
N1	0.0425 (7)	0.0262 (6)	0.0262 (6)	0.0024 (5)	0.0164 (6)	0.0043 (5)
N2	0.0427 (7)	0.0197 (5)	0.0247 (6)	0.0004 (5)	0.0175 (5)	0.0007 (5)
N3	0.0297 (6)	0.0216 (5)	0.0227 (6)	0.0011 (4)	0.0095 (5)	0.0007 (4)
N4	0.0316 (6)	0.0180 (5)	0.0222 (6)	0.0008 (4)	0.0106 (5)	0.0025 (4)
C1	0.0247 (6)	0.0266 (6)	0.0216 (6)	0.0011 (5)	0.0069 (5)	0.0015 (5)
C2	0.0268 (6)	0.0193 (6)	0.0214 (6)	0.0013 (5)	0.0074 (5)	0.0007 (5)
C3	0.0242 (6)	0.0199 (6)	0.0207 (6)	0.0006 (5)	0.0052 (5)	0.0003 (5)
C4	0.0287 (7)	0.0208 (6)	0.0262 (7)	−0.0004 (5)	0.0062 (5)	0.0009 (5)
C5	0.0350 (7)	0.0226 (6)	0.0293 (8)	0.0010 (5)	0.0064 (6)	−0.0063 (5)
C6	0.0346 (8)	0.0320 (7)	0.0233 (7)	0.0021 (6)	0.0081 (6)	−0.0056 (6)
C7	0.0323 (7)	0.0281 (7)	0.0209 (7)	0.0007 (5)	0.0087 (5)	0.0007 (5)
C8	0.0246 (6)	0.0198 (6)	0.0202 (6)	0.0020 (5)	0.0048 (5)	0.0005 (5)
C9	0.0306 (7)	0.0204 (6)	0.0226 (6)	0.0006 (5)	0.0091 (5)	0.0015 (5)
C10	0.0313 (7)	0.0202 (6)	0.0274 (7)	−0.0029 (5)	0.0095 (6)	0.0035 (5)
C11	0.0336 (7)	0.0268 (7)	0.0400 (9)	−0.0001 (6)	0.0107 (6)	0.0105 (6)
C12	0.0383 (8)	0.0219 (6)	0.0370 (8)	0.0034 (6)	0.0104 (7)	0.0079 (6)
C13	0.0341 (7)	0.0207 (6)	0.0373 (8)	−0.0011 (5)	0.0077 (6)	0.0058 (6)
C14	0.0350 (8)	0.0240 (7)	0.0361 (8)	0.0001 (6)	0.0082 (6)	0.0077 (6)
C15	0.0345 (8)	0.0281 (7)	0.0345 (8)	−0.0001 (6)	0.0076 (6)	0.0064 (6)
C16	0.0367 (8)	0.0304 (7)	0.0366 (9)	0.0013 (6)	0.0102 (7)	0.0080 (6)
C17	0.0451 (9)	0.0427 (10)	0.0453 (10)	0.0034 (7)	0.0186 (8)	0.0095 (8)
C18	0.0539 (11)	0.0584 (12)	0.0445 (11)	−0.0115 (9)	0.0185 (9)	0.0095 (9)
C19	0.0836 (15)	0.0492 (11)	0.0392 (10)	−0.0012 (10)	0.0159 (10)	0.0104 (9)

Geometric parameters (Å, º) top

S1—C1	1.6723 (14)	C11—C12	1.531 (2)
O1—C9	1.2320 (17)	C11—H11A	0.9900
N1—C1	1.3204 (18)	C11—H11B	0.9900
N1—H11	0.864 (9)	C12—C13	1.518 (2)
N1—H12	0.865 (9)	C12—H12A	0.9900
N2—N3	1.3537 (16)	C12—H12B	0.9900
N2—C1	1.3673 (17)	C13—C14	1.5235 (19)
N2—H2	0.858 (9)	C13—H13A	0.9900
N3—C2	1.2924 (17)	C13—H13B	0.9900
N4—C9	1.3556 (17)	C14—C15	1.521 (2)
N4—C8	1.4132 (16)	C14—H14A	0.9900
N4—C10	1.4613 (17)	C14—H14B	0.9900
C2—C3	1.4521 (18)	C15—C16	1.520 (2)
C2—C9	1.5014 (18)	C15—H15A	0.9900
C3—C4	1.3833 (18)	C15—H15B	0.9900
C3—C8	1.4004 (18)	C16—C17	1.521 (2)
C4—C5	1.3928 (19)	C16—H16A	0.9900
C4—H4	0.9500	C16—H16B	0.9900
C5—C6	1.385 (2)	C17—C18	1.529 (3)
C5—H5	0.9500	C17—H17A	0.9900
C6—C7	1.392 (2)	C17—H17B	0.9900
C6—H6	0.9500	C18—C19	1.499 (3)
C7—C8	1.3831 (18)	C18—H18A	0.9900
C7—H7	0.9500	C18—H18B	0.9900
C10—C11	1.513 (2)	C19—H19A	0.9800
C10—H10A	0.9900	C19—H19B	0.9800
C10—H10B	0.9900	C19—H19C	0.9800

C1—N1—H11	119.6 (15)	C13—C12—C11	114.51 (13)
C1—N1—H12	119.8 (13)	C13—C12—H12A	108.6
H11—N1—H12	119.9 (19)	C11—C12—H12A	108.6
N3—N2—C1	121.24 (12)	C13—C12—H12B	108.6
N3—N2—H2	117.5 (13)	C11—C12—H12B	108.6
C1—N2—H2	121.3 (13)	H12A—C12—H12B	107.6
C2—N3—N2	115.75 (11)	C12—C13—C14	113.07 (12)
C9—N4—C8	110.65 (11)	C12—C13—H13A	109.0
C9—N4—C10	122.93 (11)	C14—C13—H13A	109.0
C8—N4—C10	126.41 (11)	C12—C13—H13B	109.0
N1—C1—N2	116.36 (12)	C14—C13—H13B	109.0
N1—C1—S1	125.81 (11)	H13A—C13—H13B	107.8
N2—C1—S1	117.83 (10)	C13—C14—C15	113.72 (13)
N3—C2—C3	126.45 (12)	C13—C14—H14A	108.8
N3—C2—C9	127.20 (12)	C15—C14—H14A	108.8
C3—C2—C9	106.33 (11)	C13—C14—H14B	108.8
C4—C3—C8	120.36 (12)	C15—C14—H14B	108.8
C4—C3—C2	132.97 (12)	H14A—C14—H14B	107.7
C8—C3—C2	106.64 (11)	C16—C15—C14	114.32 (13)
C3—C4—C5	118.21 (13)	C16—C15—H15A	108.7
C3—C4—H4	120.9	C14—C15—H15A	108.7
C5—C4—H4	120.9	C16—C15—H15B	108.7
C6—C5—C4	120.72 (13)	C14—C15—H15B	108.7
C6—C5—H5	119.6	H15A—C15—H15B	107.6
C4—C5—H5	119.6	C15—C16—C17	112.24 (14)
C5—C6—C7	121.85 (13)	C15—C16—H16A	109.2
C5—C6—H6	119.1	C17—C16—H16A	109.2
C7—C6—H6	119.1	C15—C16—H16B	109.2
C8—C7—C6	116.91 (13)	C17—C16—H16B	109.2
C8—C7—H7	121.5	H16A—C16—H16B	107.9
C6—C7—H7	121.5	C16—C17—C18	114.67 (16)
C7—C8—C3	121.95 (12)	C16—C17—H17A	108.6
C7—C8—N4	128.32 (12)	C18—C17—H17A	108.6
C3—C8—N4	109.70 (11)	C16—C17—H17B	108.6
O1—C9—N4	126.06 (12)	C18—C17—H17B	108.6
O1—C9—C2	127.26 (12)	H17A—C17—H17B	107.6
N4—C9—C2	106.67 (11)	C19—C18—C17	112.98 (16)
N4—C10—C11	112.26 (12)	C19—C18—H18A	109.0
N4—C10—H10A	109.2	C17—C18—H18A	109.0
C11—C10—H10A	109.2	C19—C18—H18B	109.0
N4—C10—H10B	109.2	C17—C18—H18B	109.0
C11—C10—H10B	109.2	H18A—C18—H18B	107.8
H10A—C10—H10B	107.9	C18—C19—H19A	109.5
C10—C11—C12	112.20 (12)	C18—C19—H19B	109.5
C10—C11—H11A	109.2	H19A—C19—H19B	109.5
C12—C11—H11A	109.2	C18—C19—H19C	109.5
C10—C11—H11B	109.2	H19A—C19—H19C	109.5
C12—C11—H11B	109.2	H19B—C19—H19C	109.5
H11A—C11—H11B	107.9

C1—N2—N3—C2	177.49 (13)	C10—N4—C8—C7	−1.2 (2)
N3—N2—C1—N1	−2.0 (2)	C9—N4—C8—C3	−0.06 (16)
N3—N2—C1—S1	177.49 (10)	C10—N4—C8—C3	−179.47 (12)
N2—N3—C2—C3	−179.58 (13)	C8—N4—C9—O1	−178.82 (14)
N2—N3—C2—C9	−1.7 (2)	C10—N4—C9—O1	0.6 (2)
N3—C2—C3—C4	0.7 (2)	C8—N4—C9—C2	0.34 (15)
C9—C2—C3—C4	−177.54 (15)	C10—N4—C9—C2	179.77 (12)
N3—C2—C3—C8	178.72 (13)	N3—C2—C9—O1	0.4 (2)
C9—C2—C3—C8	0.44 (14)	C3—C2—C9—O1	178.66 (14)
C8—C3—C4—C5	0.6 (2)	N3—C2—C9—N4	−178.74 (13)
C2—C3—C4—C5	178.39 (14)	C3—C2—C9—N4	−0.48 (15)
C3—C4—C5—C6	−0.4 (2)	C9—N4—C10—C11	83.30 (17)
C4—C5—C6—C7	−0.1 (2)	C8—N4—C10—C11	−97.36 (16)
C5—C6—C7—C8	0.4 (2)	N4—C10—C11—C12	−179.72 (12)
C6—C7—C8—C3	−0.2 (2)	C10—C11—C12—C13	−78.90 (18)
C6—C7—C8—N4	−178.24 (14)	C11—C12—C13—C14	−176.76 (13)
C4—C3—C8—C7	−0.4 (2)	C12—C13—C14—C15	175.33 (13)
C2—C3—C8—C7	−178.65 (12)	C13—C14—C15—C16	−177.44 (13)
C4—C3—C8—N4	178.04 (12)	C14—C15—C16—C17	−174.78 (14)
C2—C3—C8—N4	−0.25 (15)	C15—C16—C17—C18	172.62 (15)
C9—N4—C8—C7	178.21 (14)	C16—C17—C18—C19	69.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···S1ⁱ	0.87 (1)	2.81 (1)	3.628 (1)	159 (2)
N1—H11···O1ⁱ	0.86 (1)	2.19 (1)	2.986 (2)	154 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈N₄OS
M_r	360.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	180
a, b, c (Å)	11.8856 (2), 11.0055 (2), 15.1638 (3)
β (°)	99.468 (1)
V (Å³)	1956.51 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.23 × 0.14 × 0.12

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	26304, 5715, 4227
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.135, 1.06
No. of reflections	5715
No. of parameters	238
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)	0.30, −0.36

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—H11···O1ⁱ	0.86 (1)	2.19 (1)	2.986 (2)	154 (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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