3-Acetyl-5-methyl-1-(4-methyl­phen­yl)-1H-pyrazole-4-carboxamide

Abdel-Aziz, H.A.; Bari, A.; Ng, S.W.

doi:10.1107/S1600536810043928

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3010

https://doi.org/10.1107/S1600536810043928

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3-Acetyl-5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide

Hatem A. Abdel-Aziz,^a Ahmed Bari ^a and Seik Weng Ng ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 October 2010; accepted 27 October 2010; online 31 October 2010)

In the title compound, C₁₄H₁₅N₃O₂, the phenylene ring is disordered over two orientations. As a result, the almost planar pyrazole ring (r.m.s. deviation = 0.004 Å) forms dihedral angles of 59.8 (1) and −61.9 (1)° with the two orientations of the phenylene ring. The dihedral angle between the two orientations is 59.2 (1)°. In the crystal, inversion dimers lined by pairs of N—H⋯O hydrogen bonds occur; there is also an intramolecular N—H⋯O bond.

Related literature

For the synthesis of the title compound, see: Ibrahim et al. (1992 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₂
M_r = 257.29
Triclinic, $[P \overline 1]$
a = 5.0521 (6) Å
b = 10.4068 (13) Å
c = 12.6558 (16) Å
α = 103.295 (2)°
β = 95.338 (2)°
γ = 100.072 (2)°
V = 631.39 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
6045 measured reflections
2873 independent reflections
2002 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.152
S = 1.03
2873 reflections
230 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯O1	0.88 (3)	1.95 (2)	2.771 (2)	154 (3)
N3—H32⋯O2ⁱ	0.89 (3)	2.02 (1)	2.906 (3)	177 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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/S1600536810043928/bt5394sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043928/bt5394Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives have been studied in the context of its biological properties. One class of such compounds is synthesized by reaction of hydrazidolyl chlorides active methylene comounds in basic medium (Ibrahim et al., 1992). The hydrazidolyl chloride in the present study is 2-oxo-N'-(4-tolyl)propanehydrazolyl chloride; this reacts with 3-oxobutanamide to yield the title compound (Scheme I). In the title molecule, the phenylene ring adopts two orientations. One orientation has the ring aligned at about 60° and the other has the ring aligned at about -60° with respect to the pyrazoly ring. The two orientations are stagged by another 60°. Two molecules are linked by an N—H···O hydrogen bond about a center-of-inversion to form a dimer. (Fig. 1).

Related literature top

For the synthesis of the title compound, see: Ibrahim et al. (1992).

Experimental top

Sodium metal (0.023 g, 1 mmol) was dissolved in absolute ethanol (50 ml); to the solution of sodium ethoxide was added 3-oxobutanamide (0.10 g, 10 mmol). To the clear solution was added 2-oxo-N'-(4-tolyl)propanehydrazolyl chloride (0.21 g, 1 mmol). The reaction mixture was set aside for 12 h. Water was added to precipitate the product, which was collected and dried. The compound was recrystallized from ethanol to yield yellow prisms.

Structure description top

For the synthesis of the title compound, see: Ibrahim et al. (1992).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 ellipsoid plot (Barbour, 2001) of the title compound showing two molecules related by a center-of-inversion and held together by hydrogen bonds. The probability level is set at 70%; H atoms are drawn as spheres of arbitrary radius, and the disorder is not shown.

3-Acetyl-5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxamide top

Crystal data top

C₁₄H₁₅N₃O₂	Z = 2
M_r = 257.29	F(000) = 272
Triclinic, P1	D_x = 1.353 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0521 (6) Å	Cell parameters from 1604 reflections
b = 10.4068 (13) Å	θ = 3.0–27.9°
c = 12.6558 (16) Å	µ = 0.09 mm⁻¹
α = 103.295 (2)°	T = 100 K
β = 95.338 (2)°	Prism, yellow
γ = 100.072 (2)°	0.30 × 0.06 × 0.03 mm
V = 631.39 (13) Å³

Data collection top

Bruker SMART APEX diffractometer	2002 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω scans	h = −6→6
6045 measured reflections	k = −13→13
2873 independent reflections	l = −16→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0719P)² + 0.3595P] where P = (F_o² + 2F_c²)/3
2873 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.29 e Å⁻³
5 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₄H₁₅N₃O₂	γ = 100.072 (2)°
M_r = 257.29	V = 631.39 (13) Å³
Triclinic, P1	Z = 2
a = 5.0521 (6) Å	Mo Kα radiation
b = 10.4068 (13) Å	µ = 0.09 mm⁻¹
c = 12.6558 (16) Å	T = 100 K
α = 103.295 (2)°	0.30 × 0.06 × 0.03 mm
β = 95.338 (2)°

Data collection top

Bruker SMART APEX diffractometer	2002 reflections with I > 2σ(I)
6045 measured reflections	R_int = 0.030
2873 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	5 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.29 e Å⁻³
2873 reflections	Δρ_min = −0.34 e Å⁻³
230 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.1305 (3)	0.14044 (15)	0.52867 (12)	0.0268 (4)
O2	0.6699 (3)	0.4493 (2)	0.61411 (15)	0.0452 (5)
N1	0.4515 (3)	0.23144 (16)	0.84070 (13)	0.0174 (4)
N2	0.2167 (3)	0.15038 (17)	0.78625 (14)	0.0184 (4)
N3	0.2489 (4)	0.3669 (2)	0.52691 (17)	0.0345 (5)
C1	0.5330 (4)	0.23207 (19)	0.95263 (16)	0.0172 (4)
C2	0.5929 (9)	0.1193 (4)	0.9788 (3)	0.0224 (9)	0.50
H2	0.5835	0.0389	0.9235	0.027*	0.50
C3	0.6675 (9)	0.1253 (4)	1.0878 (4)	0.0255 (10)	0.50
H3	0.7061	0.0467	1.1069	0.031*	0.50
C4	0.6885 (4)	0.2436 (2)	1.17193 (17)	0.0232 (5)
C5	0.6121 (8)	0.3527 (4)	1.1393 (3)	0.0199 (8)	0.50
H5	0.6103	0.4322	1.1939	0.024*	0.50
C6	0.5386 (8)	0.3491 (4)	1.0303 (3)	0.0210 (8)	0.50
H6	0.4933	0.4257	1.0098	0.025*	0.50
C7	0.7753 (5)	0.2541 (3)	1.2913 (2)	0.0349 (6)
H7A	0.643 (6)	0.288 (4)	1.336 (3)	0.088 (13)*
H7B	0.958 (3)	0.309 (3)	1.312 (3)	0.064 (10)*
H7C	0.782 (6)	0.1647 (16)	1.302 (3)	0.058 (9)*
C8	0.8281 (4)	0.4154 (2)	0.82810 (17)	0.0206 (4)
H8A	0.9078	0.3966	0.8951	0.031*
H8B	0.7935	0.5072	0.8451	0.031*
H8C	0.9542	0.4070	0.7737	0.031*
C9	0.5672 (4)	0.31710 (19)	0.78304 (17)	0.0185 (4)
C10	0.3949 (4)	0.29140 (19)	0.68544 (16)	0.0179 (4)
C11	0.1794 (4)	0.18543 (19)	0.69107 (16)	0.0172 (4)
C12	−0.0704 (4)	0.1115 (2)	0.61502 (17)	0.0187 (4)
C13	−0.2497 (4)	0.0000 (2)	0.64740 (18)	0.0219 (5)
H13A	−0.4213	−0.0288	0.5975	0.033*
H13B	−0.2862	0.0325	0.7226	0.033*
H13C	−0.1586	−0.0764	0.6432	0.033*
C14	0.4481 (4)	0.3732 (2)	0.60424 (17)	0.0201 (4)
C2'	0.7886 (8)	0.2071 (4)	0.9862 (4)	0.0223 (9)	0.50
H2'	0.9071	0.1855	0.9337	0.027*	0.50
C3'	0.8673 (8)	0.2140 (4)	1.0949 (4)	0.0245 (9)	0.50
H3'	1.0412	0.1989	1.1178	0.029*	0.50
C5'	0.4431 (9)	0.2659 (5)	1.1399 (4)	0.0268 (10)	0.50
H5'	0.3240	0.2862	1.1923	0.032*	0.50
C6'	0.3625 (9)	0.2593 (4)	1.0304 (3)	0.0226 (9)	0.50
H6'	0.1872	0.2738	1.0088	0.027*	0.50
H31	0.093 (4)	0.311 (3)	0.522 (3)	0.059 (9)*
H32	0.280 (6)	0.422 (2)	0.484 (2)	0.051 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0255 (8)	0.0296 (8)	0.0230 (8)	−0.0029 (6)	−0.0035 (6)	0.0114 (6)
O2	0.0267 (9)	0.0648 (13)	0.0474 (12)	−0.0126 (8)	−0.0049 (8)	0.0411 (10)
N1	0.0167 (8)	0.0169 (8)	0.0174 (9)	0.0004 (6)	−0.0008 (6)	0.0054 (7)
N2	0.0151 (8)	0.0192 (8)	0.0191 (9)	0.0005 (6)	−0.0009 (7)	0.0048 (7)
N3	0.0266 (10)	0.0430 (13)	0.0344 (12)	−0.0089 (9)	−0.0065 (9)	0.0266 (10)
C1	0.0174 (9)	0.0174 (9)	0.0161 (10)	0.0000 (7)	−0.0006 (7)	0.0063 (8)
C2	0.027 (2)	0.0164 (19)	0.019 (2)	−0.0017 (16)	−0.0016 (17)	0.0004 (16)
C3	0.034 (2)	0.018 (2)	0.025 (2)	−0.0007 (17)	−0.0039 (18)	0.0129 (17)
C4	0.0245 (10)	0.0233 (11)	0.0194 (11)	−0.0038 (8)	−0.0009 (8)	0.0087 (8)
C5	0.0180 (19)	0.022 (2)	0.017 (2)	0.0020 (16)	0.0031 (15)	0.0010 (16)
C6	0.0204 (19)	0.023 (2)	0.020 (2)	0.0039 (16)	0.0012 (16)	0.0069 (16)
C7	0.0383 (14)	0.0406 (15)	0.0241 (13)	−0.0015 (11)	−0.0047 (11)	0.0154 (11)
C8	0.0189 (10)	0.0205 (10)	0.0220 (11)	0.0012 (8)	0.0013 (8)	0.0072 (8)
C9	0.0189 (10)	0.0161 (9)	0.0211 (10)	0.0039 (8)	0.0038 (8)	0.0053 (8)
C10	0.0187 (9)	0.0174 (10)	0.0175 (10)	0.0036 (8)	0.0033 (8)	0.0039 (8)
C11	0.0169 (9)	0.0164 (9)	0.0186 (10)	0.0037 (7)	0.0031 (8)	0.0043 (8)
C12	0.0175 (9)	0.0183 (10)	0.0204 (11)	0.0043 (8)	0.0032 (8)	0.0043 (8)
C13	0.0200 (10)	0.0219 (10)	0.0221 (11)	−0.0017 (8)	0.0005 (8)	0.0076 (8)
C14	0.0207 (10)	0.0190 (10)	0.0213 (11)	0.0033 (8)	0.0040 (8)	0.0067 (8)
C2'	0.0161 (19)	0.026 (2)	0.026 (2)	0.0033 (16)	0.0012 (16)	0.0100 (17)
C3'	0.0155 (19)	0.029 (2)	0.028 (2)	−0.0003 (16)	−0.0057 (17)	0.0122 (18)
C5'	0.033 (2)	0.026 (2)	0.020 (2)	0.0043 (19)	0.0007 (18)	0.0058 (18)
C6'	0.026 (2)	0.021 (2)	0.022 (2)	0.0069 (17)	−0.0035 (17)	0.0092 (17)

Geometric parameters (Å, º) top

O1—C12	1.224 (2)	C6—H6	0.9500
O2—C14	1.232 (3)	C7—H7A	0.980 (10)
N1—N2	1.351 (2)	C7—H7B	0.975 (10)
N1—C9	1.366 (3)	C7—H7C	0.977 (10)
N1—C1	1.436 (3)	C8—C9	1.493 (3)
N2—C11	1.343 (3)	C8—H8A	0.9800
N3—C14	1.319 (3)	C8—H8B	0.9800
N3—H31	0.88 (3)	C8—H8C	0.9800
N3—H32	0.89 (3)	C9—C10	1.386 (3)
C1—C2	1.365 (5)	C10—C11	1.427 (3)
C1—C6	1.372 (5)	C10—C14	1.492 (3)
C1—C6'	1.381 (5)	C11—C12	1.485 (3)
C1—C2'	1.408 (4)	C12—C13	1.502 (3)
C2—C3	1.380 (6)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.412 (5)	C13—H13C	0.9800
C3—H3	0.9500	C2'—C3'	1.379 (6)
C4—C5'	1.344 (5)	C2'—H2'	0.9500
C4—C5	1.395 (5)	C3'—H3'	0.9500
C4—C3'	1.408 (5)	C5'—C6'	1.390 (6)
C4—C7	1.507 (3)	C5'—H5'	0.9500
C5—C6	1.386 (6)	C6'—H6'	0.9500
C5—H5	0.9500

N2—N1—C9	112.79 (16)	H7B—C7—H7C	108 (3)
N2—N1—C1	119.30 (15)	C9—C8—H8A	109.5
C9—N1—C1	127.38 (16)	C9—C8—H8B	109.5
C11—N2—N1	105.11 (15)	H8A—C8—H8B	109.5
C14—N3—H31	119 (2)	C9—C8—H8C	109.5
C14—N3—H32	117 (2)	H8A—C8—H8C	109.5
H31—N3—H32	124 (3)	H8B—C8—H8C	109.5
C2—C1—C6	122.6 (3)	N1—C9—C10	106.38 (17)
C2—C1—C6'	96.6 (3)	N1—C9—C8	121.63 (18)
C6—C1—C6'	50.4 (3)	C10—C9—C8	131.98 (18)
C2—C1—C2'	51.4 (3)	C9—C10—C11	104.86 (17)
C6—C1—C2'	99.4 (3)	C9—C10—C14	121.36 (17)
C6'—C1—C2'	118.4 (3)	C11—C10—C14	133.68 (18)
C2—C1—N1	120.7 (2)	N2—C11—C10	110.85 (17)
C6—C1—N1	116.7 (2)	N2—C11—C12	116.22 (17)
C6'—C1—N1	120.4 (2)	C10—C11—C12	132.92 (18)
C2'—C1—N1	121.1 (2)	O1—C12—C11	121.39 (18)
C1—C2—C3	118.2 (4)	O1—C12—C13	120.63 (18)
C1—C2—H2	120.9	C11—C12—C13	117.98 (18)
C3—C2—H2	120.9	C12—C13—H13A	109.5
C2—C3—C4	122.5 (4)	C12—C13—H13B	109.5
C2—C3—H3	118.8	H13A—C13—H13B	109.5
C4—C3—H3	118.8	C12—C13—H13C	109.5
C5'—C4—C3'	120.3 (3)	H13A—C13—H13C	109.5
C5—C4—C3	115.9 (3)	H13B—C13—H13C	109.5
C5'—C4—C7	119.8 (3)	O2—C14—N3	121.8 (2)
C5—C4—C7	120.3 (3)	O2—C14—C10	119.67 (19)
C3'—C4—C7	119.9 (3)	N3—C14—C10	118.44 (18)
C3—C4—C7	123.7 (3)	C3'—C2'—C1	120.2 (4)
C6—C5—C4	122.4 (4)	C3'—C2'—H2'	119.9
C6—C5—H5	118.8	C1—C2'—H2'	119.9
C4—C5—H5	118.8	C2'—C3'—C4	119.6 (4)
C1—C6—C5	118.3 (4)	C2'—C3'—H3'	120.2
C1—C6—H6	120.9	C4—C3'—H3'	120.2
C5—C6—H6	120.9	C4—C5'—C6'	120.4 (4)
C4—C7—H7A	111 (2)	C4—C5'—H5'	119.8
C4—C7—H7B	108 (2)	C6'—C5'—H5'	119.8
H7A—C7—H7B	114 (3)	C1—C6'—C5'	121.1 (4)
C4—C7—H7C	109.8 (19)	C1—C6'—H6'	119.5
H7A—C7—H7C	106 (3)	C5'—C6'—H6'	119.5

C9—N1—N2—C11	−0.3 (2)	N1—C9—C10—C14	176.00 (18)
C1—N1—N2—C11	171.92 (17)	C8—C9—C10—C14	−3.1 (3)
N2—N1—C1—C2	64.4 (3)	N1—N2—C11—C10	−0.3 (2)
C9—N1—C1—C2	−124.6 (3)	N1—N2—C11—C12	−179.27 (16)
N2—N1—C1—C6	−113.7 (3)	C9—C10—C11—N2	0.7 (2)
C9—N1—C1—C6	57.3 (3)	C14—C10—C11—N2	−175.6 (2)
N2—N1—C1—C6'	−55.8 (3)	C9—C10—C11—C12	179.5 (2)
C9—N1—C1—C6'	115.2 (3)	C14—C10—C11—C12	3.2 (4)
N2—N1—C1—C2'	125.1 (3)	N2—C11—C12—O1	176.23 (19)
C9—N1—C1—C2'	−63.8 (3)	C10—C11—C12—O1	−2.5 (3)
C6—C1—C2—C3	−1.4 (5)	N2—C11—C12—C13	−3.4 (3)
C6'—C1—C2—C3	−48.0 (4)	C10—C11—C12—C13	177.8 (2)
C2'—C1—C2—C3	73.4 (4)	C9—C10—C14—O2	12.5 (3)
N1—C1—C2—C3	−179.4 (3)	C11—C10—C14—O2	−171.7 (2)
C1—C2—C3—C4	−1.2 (6)	C9—C10—C14—N3	−163.9 (2)
C2—C3—C4—C5'	50.2 (5)	C11—C10—C14—N3	12.0 (4)
C2—C3—C4—C5	4.0 (5)	C2—C1—C2'—C3'	−76.6 (4)
C2—C3—C4—C3'	−75.0 (4)	C6—C1—C2'—C3'	48.0 (4)
C2—C3—C4—C7	−178.6 (3)	C6'—C1—C2'—C3'	−1.9 (5)
C5'—C4—C5—C6	−77.4 (4)	N1—C1—C2'—C3'	177.2 (3)
C3'—C4—C5—C6	46.3 (4)	C1—C2'—C3'—C4	1.2 (6)
C3—C4—C5—C6	−4.5 (5)	C5'—C4—C3'—C2'	−0.4 (5)
C7—C4—C5—C6	178.0 (3)	C5—C4—C3'—C2'	−46.8 (4)
C2—C1—C6—C5	1.0 (5)	C3—C4—C3'—C2'	70.1 (4)
C6'—C1—C6—C5	70.3 (4)	C7—C4—C3'—C2'	−178.8 (3)
C2'—C1—C6—C5	−48.9 (4)	C5—C4—C5'—C6'	72.9 (4)
N1—C1—C6—C5	179.0 (3)	C3'—C4—C5'—C6'	0.3 (6)
C4—C5—C6—C1	2.2 (6)	C3—C4—C5'—C6'	−47.5 (4)
N2—N1—C9—C10	0.8 (2)	C7—C4—C5'—C6'	178.7 (3)
C1—N1—C9—C10	−170.69 (18)	C2—C1—C6'—C5'	51.2 (4)
N2—N1—C9—C8	−179.98 (17)	C6—C1—C6'—C5'	−76.3 (4)
C1—N1—C9—C8	8.5 (3)	C2'—C1—C6'—C5'	1.8 (5)
N1—C9—C10—C11	−0.9 (2)	N1—C1—C6'—C5'	−177.3 (3)
C8—C9—C10—C11	−180.0 (2)	C4—C5'—C6'—C1	−1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O1	0.88 (3)	1.95 (2)	2.771 (2)	154 (3)
N3—H32···O2ⁱ	0.89 (3)	2.02 (1)	2.906 (3)	177 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₂
M_r	257.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.0521 (6), 10.4068 (13), 12.6558 (16)
α, β, γ (°)	103.295 (2), 95.338 (2), 100.072 (2)
V (Å³)	631.39 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.06 × 0.03

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6045, 2873, 2002
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.152, 1.03
No. of reflections	2873
No. of parameters	230
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N3—H31···O1	0.88 (3)	1.95 (2)	2.771 (2)	154 (3)
N3—H32···O2ⁱ	0.89 (3)	2.02 (1)	2.906 (3)	177 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank King Saud University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ibrahim, M. K. A., Elghandour, A. H. H., Abou-Hadeed, K. & Abdelhafiz, I. S. (1992). J. Indian Chem. Soc. 69, 378–380. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar