organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Ibrahim, M. K. A., Elghandour, A. H. H., Abou-Hadeed, K. & Abdelhafiz, I. S. (1992). J. Indian Chem. Soc. 69, 378-380.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15N3O2

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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.

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5 times Ueq(C).

The amino H atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N—H 0.88 (1) Å.

The phenylene ring is disordered along the Cipso—Cpara axis; as the disorder refined to nearly 1:1, the ratio was then fixed as exactly 1:1. No restraints were imposed. As the two orientations differ by 60°, the H atoms of the methyl group are ordered. These were refined isotropically with a distance restraint of C—H 0.98 (1) Å.

Structure description 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).

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
[Figure 1] 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
C14H15N3O2Z = 2
Mr = 257.29F(000) = 272
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0521 (6) ÅCell parameters from 1604 reflections
b = 10.4068 (13) Åθ = 3.0–27.9°
c = 12.6558 (16) ŵ = 0.09 mm1
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 tubeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
ω scansh = 66
6045 measured reflectionsk = 1313
2873 independent reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0719P)2 + 0.3595P]
where P = (Fo2 + 2Fc2)/3
2873 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 0.29 e Å3
5 restraintsΔρmin = 0.34 e Å3
Crystal data top
C14H15N3O2γ = 100.072 (2)°
Mr = 257.29V = 631.39 (13) Å3
Triclinic, P1Z = 2
a = 5.0521 (6) ÅMo Kα radiation
b = 10.4068 (13) ŵ = 0.09 mm1
c = 12.6558 (16) ÅT = 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 reflectionsRint = 0.030
2873 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0505 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.29 e Å3
2873 reflectionsΔρmin = 0.34 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.1305 (3)0.14044 (15)0.52867 (12)0.0268 (4)
O20.6699 (3)0.4493 (2)0.61411 (15)0.0452 (5)
N10.4515 (3)0.23144 (16)0.84070 (13)0.0174 (4)
N20.2167 (3)0.15038 (17)0.78625 (14)0.0184 (4)
N30.2489 (4)0.3669 (2)0.52691 (17)0.0345 (5)
C10.5330 (4)0.23207 (19)0.95263 (16)0.0172 (4)
C20.5929 (9)0.1193 (4)0.9788 (3)0.0224 (9)0.50
H20.58350.03890.92350.027*0.50
C30.6675 (9)0.1253 (4)1.0878 (4)0.0255 (10)0.50
H30.70610.04671.10690.031*0.50
C40.6885 (4)0.2436 (2)1.17193 (17)0.0232 (5)
C50.6121 (8)0.3527 (4)1.1393 (3)0.0199 (8)0.50
H50.61030.43221.19390.024*0.50
C60.5386 (8)0.3491 (4)1.0303 (3)0.0210 (8)0.50
H60.49330.42571.00980.025*0.50
C70.7753 (5)0.2541 (3)1.2913 (2)0.0349 (6)
H7A0.643 (6)0.288 (4)1.336 (3)0.088 (13)*
H7B0.958 (3)0.309 (3)1.312 (3)0.064 (10)*
H7C0.782 (6)0.1647 (16)1.302 (3)0.058 (9)*
C80.8281 (4)0.4154 (2)0.82810 (17)0.0206 (4)
H8A0.90780.39660.89510.031*
H8B0.79350.50720.84510.031*
H8C0.95420.40700.77370.031*
C90.5672 (4)0.31710 (19)0.78304 (17)0.0185 (4)
C100.3949 (4)0.29140 (19)0.68544 (16)0.0179 (4)
C110.1794 (4)0.18543 (19)0.69107 (16)0.0172 (4)
C120.0704 (4)0.1115 (2)0.61502 (17)0.0187 (4)
C130.2497 (4)0.0000 (2)0.64740 (18)0.0219 (5)
H13A0.42130.02880.59750.033*
H13B0.28620.03250.72260.033*
H13C0.15860.07640.64320.033*
C140.4481 (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
H2'0.90710.18550.93370.027*0.50
C3'0.8673 (8)0.2140 (4)1.0949 (4)0.0245 (9)0.50
H3'1.04120.19891.11780.029*0.50
C5'0.4431 (9)0.2659 (5)1.1399 (4)0.0268 (10)0.50
H5'0.32400.28621.19230.032*0.50
C6'0.3625 (9)0.2593 (4)1.0304 (3)0.0226 (9)0.50
H6'0.18720.27381.00880.027*0.50
H310.093 (4)0.311 (3)0.522 (3)0.059 (9)*
H320.280 (6)0.422 (2)0.484 (2)0.051 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0255 (8)0.0296 (8)0.0230 (8)0.0029 (6)0.0035 (6)0.0114 (6)
O20.0267 (9)0.0648 (13)0.0474 (12)0.0126 (8)0.0049 (8)0.0411 (10)
N10.0167 (8)0.0169 (8)0.0174 (9)0.0004 (6)0.0008 (6)0.0054 (7)
N20.0151 (8)0.0192 (8)0.0191 (9)0.0005 (6)0.0009 (7)0.0048 (7)
N30.0266 (10)0.0430 (13)0.0344 (12)0.0089 (9)0.0065 (9)0.0266 (10)
C10.0174 (9)0.0174 (9)0.0161 (10)0.0000 (7)0.0006 (7)0.0063 (8)
C20.027 (2)0.0164 (19)0.019 (2)0.0017 (16)0.0016 (17)0.0004 (16)
C30.034 (2)0.018 (2)0.025 (2)0.0007 (17)0.0039 (18)0.0129 (17)
C40.0245 (10)0.0233 (11)0.0194 (11)0.0038 (8)0.0009 (8)0.0087 (8)
C50.0180 (19)0.022 (2)0.017 (2)0.0020 (16)0.0031 (15)0.0010 (16)
C60.0204 (19)0.023 (2)0.020 (2)0.0039 (16)0.0012 (16)0.0069 (16)
C70.0383 (14)0.0406 (15)0.0241 (13)0.0015 (11)0.0047 (11)0.0154 (11)
C80.0189 (10)0.0205 (10)0.0220 (11)0.0012 (8)0.0013 (8)0.0072 (8)
C90.0189 (10)0.0161 (9)0.0211 (10)0.0039 (8)0.0038 (8)0.0053 (8)
C100.0187 (9)0.0174 (10)0.0175 (10)0.0036 (8)0.0033 (8)0.0039 (8)
C110.0169 (9)0.0164 (9)0.0186 (10)0.0037 (7)0.0031 (8)0.0043 (8)
C120.0175 (9)0.0183 (10)0.0204 (11)0.0043 (8)0.0032 (8)0.0043 (8)
C130.0200 (10)0.0219 (10)0.0221 (11)0.0017 (8)0.0005 (8)0.0076 (8)
C140.0207 (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—C121.224 (2)C6—H60.9500
O2—C141.232 (3)C7—H7A0.980 (10)
N1—N21.351 (2)C7—H7B0.975 (10)
N1—C91.366 (3)C7—H7C0.977 (10)
N1—C11.436 (3)C8—C91.493 (3)
N2—C111.343 (3)C8—H8A0.9800
N3—C141.319 (3)C8—H8B0.9800
N3—H310.88 (3)C8—H8C0.9800
N3—H320.89 (3)C9—C101.386 (3)
C1—C21.365 (5)C10—C111.427 (3)
C1—C61.372 (5)C10—C141.492 (3)
C1—C6'1.381 (5)C11—C121.485 (3)
C1—C2'1.408 (4)C12—C131.502 (3)
C2—C31.380 (6)C13—H13A0.9800
C2—H20.9500C13—H13B0.9800
C3—C41.412 (5)C13—H13C0.9800
C3—H30.9500C2'—C3'1.379 (6)
C4—C5'1.344 (5)C2'—H2'0.9500
C4—C51.395 (5)C3'—H3'0.9500
C4—C3'1.408 (5)C5'—C6'1.390 (6)
C4—C71.507 (3)C5'—H5'0.9500
C5—C61.386 (6)C6'—H6'0.9500
C5—H50.9500
N2—N1—C9112.79 (16)H7B—C7—H7C108 (3)
N2—N1—C1119.30 (15)C9—C8—H8A109.5
C9—N1—C1127.38 (16)C9—C8—H8B109.5
C11—N2—N1105.11 (15)H8A—C8—H8B109.5
C14—N3—H31119 (2)C9—C8—H8C109.5
C14—N3—H32117 (2)H8A—C8—H8C109.5
H31—N3—H32124 (3)H8B—C8—H8C109.5
C2—C1—C6122.6 (3)N1—C9—C10106.38 (17)
C2—C1—C6'96.6 (3)N1—C9—C8121.63 (18)
C6—C1—C6'50.4 (3)C10—C9—C8131.98 (18)
C2—C1—C2'51.4 (3)C9—C10—C11104.86 (17)
C6—C1—C2'99.4 (3)C9—C10—C14121.36 (17)
C6'—C1—C2'118.4 (3)C11—C10—C14133.68 (18)
C2—C1—N1120.7 (2)N2—C11—C10110.85 (17)
C6—C1—N1116.7 (2)N2—C11—C12116.22 (17)
C6'—C1—N1120.4 (2)C10—C11—C12132.92 (18)
C2'—C1—N1121.1 (2)O1—C12—C11121.39 (18)
C1—C2—C3118.2 (4)O1—C12—C13120.63 (18)
C1—C2—H2120.9C11—C12—C13117.98 (18)
C3—C2—H2120.9C12—C13—H13A109.5
C2—C3—C4122.5 (4)C12—C13—H13B109.5
C2—C3—H3118.8H13A—C13—H13B109.5
C4—C3—H3118.8C12—C13—H13C109.5
C5'—C4—C3'120.3 (3)H13A—C13—H13C109.5
C5—C4—C3115.9 (3)H13B—C13—H13C109.5
C5'—C4—C7119.8 (3)O2—C14—N3121.8 (2)
C5—C4—C7120.3 (3)O2—C14—C10119.67 (19)
C3'—C4—C7119.9 (3)N3—C14—C10118.44 (18)
C3—C4—C7123.7 (3)C3'—C2'—C1120.2 (4)
C6—C5—C4122.4 (4)C3'—C2'—H2'119.9
C6—C5—H5118.8C1—C2'—H2'119.9
C4—C5—H5118.8C2'—C3'—C4119.6 (4)
C1—C6—C5118.3 (4)C2'—C3'—H3'120.2
C1—C6—H6120.9C4—C3'—H3'120.2
C5—C6—H6120.9C4—C5'—C6'120.4 (4)
C4—C7—H7A111 (2)C4—C5'—H5'119.8
C4—C7—H7B108 (2)C6'—C5'—H5'119.8
H7A—C7—H7B114 (3)C1—C6'—C5'121.1 (4)
C4—C7—H7C109.8 (19)C1—C6'—H6'119.5
H7A—C7—H7C106 (3)C5'—C6'—H6'119.5
C9—N1—N2—C110.3 (2)N1—C9—C10—C14176.00 (18)
C1—N1—N2—C11171.92 (17)C8—C9—C10—C143.1 (3)
N2—N1—C1—C264.4 (3)N1—N2—C11—C100.3 (2)
C9—N1—C1—C2124.6 (3)N1—N2—C11—C12179.27 (16)
N2—N1—C1—C6113.7 (3)C9—C10—C11—N20.7 (2)
C9—N1—C1—C657.3 (3)C14—C10—C11—N2175.6 (2)
N2—N1—C1—C6'55.8 (3)C9—C10—C11—C12179.5 (2)
C9—N1—C1—C6'115.2 (3)C14—C10—C11—C123.2 (4)
N2—N1—C1—C2'125.1 (3)N2—C11—C12—O1176.23 (19)
C9—N1—C1—C2'63.8 (3)C10—C11—C12—O12.5 (3)
C6—C1—C2—C31.4 (5)N2—C11—C12—C133.4 (3)
C6'—C1—C2—C348.0 (4)C10—C11—C12—C13177.8 (2)
C2'—C1—C2—C373.4 (4)C9—C10—C14—O212.5 (3)
N1—C1—C2—C3179.4 (3)C11—C10—C14—O2171.7 (2)
C1—C2—C3—C41.2 (6)C9—C10—C14—N3163.9 (2)
C2—C3—C4—C5'50.2 (5)C11—C10—C14—N312.0 (4)
C2—C3—C4—C54.0 (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—C7178.6 (3)C6'—C1—C2'—C3'1.9 (5)
C5'—C4—C5—C677.4 (4)N1—C1—C2'—C3'177.2 (3)
C3'—C4—C5—C646.3 (4)C1—C2'—C3'—C41.2 (6)
C3—C4—C5—C64.5 (5)C5'—C4—C3'—C2'0.4 (5)
C7—C4—C5—C6178.0 (3)C5—C4—C3'—C2'46.8 (4)
C2—C1—C6—C51.0 (5)C3—C4—C3'—C2'70.1 (4)
C6'—C1—C6—C570.3 (4)C7—C4—C3'—C2'178.8 (3)
C2'—C1—C6—C548.9 (4)C5—C4—C5'—C6'72.9 (4)
N1—C1—C6—C5179.0 (3)C3'—C4—C5'—C6'0.3 (6)
C4—C5—C6—C12.2 (6)C3—C4—C5'—C6'47.5 (4)
N2—N1—C9—C100.8 (2)C7—C4—C5'—C6'178.7 (3)
C1—N1—C9—C10170.69 (18)C2—C1—C6'—C5'51.2 (4)
N2—N1—C9—C8179.98 (17)C6—C1—C6'—C5'76.3 (4)
C1—N1—C9—C88.5 (3)C2'—C1—C6'—C5'1.8 (5)
N1—C9—C10—C110.9 (2)N1—C1—C6'—C5'177.3 (3)
C8—C9—C10—C11180.0 (2)C4—C5'—C6'—C11.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···O10.88 (3)1.95 (2)2.771 (2)154 (3)
N3—H32···O2i0.89 (3)2.02 (1)2.906 (3)177 (3)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H15N3O2
Mr257.29
Crystal system, space groupTriclinic, 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)
V3)631.39 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.06 × 0.03
Data collection
DiffractometerBruker SMART APEX
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6045, 2873, 2002
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.152, 1.03
No. of reflections2873
No. of parameters230
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N3—H31···O10.88 (3)1.95 (2)2.771 (2)154 (3)
N3—H32···O2i0.89 (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

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

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