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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 1| January 2012| Page o234
doi:10.1107/S1600536811053918

2-(4-Chloro-3,3,7-tri­methyl-2,3-di­hydro-1H-indol-2-yl­­idene)-2-cyano­acetamide

Madeleine Helliwell,a Mehdi M. Baradarani,b* Maryam Alyari,b Arash Afghanc and John A. Joulea

aThe School of Chemistry, The University of Manchester, Manchester M13 9PL, England, bDepartment of Chemistry, Faculty of Science, University of Urmia, Urmia 57153-165, Iran, and cDepartment of Chemical Engineering, University of Urmia, Urmia 57153-165, Iran
*Correspondence e-mail: mmbaradarani@yahoo.com

(Received 29 November 2011; accepted 14 December 2011; online 23 December 2011)

Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C14H14ClN3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit. The orientation of the acetamide group arises from intra­molecular hydrogen bonding between the indole N—H and carbonyl groups. In the crystal, inversion-related acetamide groups form N—H⋯O hydrogen-bonded dimers in graph-set R22(8) motifs, whilst dimers are also formed by pairs of amine–nitrile N—H⋯N hydrogen bonds in R22(12) motifs. These inter­actions together generate ribbons that propagate along the b-axis direction.

Related literature

For background information on the chemistry of related compounds, see: Baradarani et al. (2006[Baradarani, M. M., Afghan, A., Zebarjadi, F., Hasanzadeh, K. & Joule, J. A. (2006). J. Heterocycl. Chem. 43, 1591-1596.]); Rashidi et al. (2009[Rashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428-431.], 2011[Rashidi, A., Baradarani, M. M. & Joule, J. A. (2011). Arkivoc, ii, 252-259.]). For related structures, see: Helliwell et al. (2010[Helliwell, M., Afghan, A., Keshvari, F., Baradarani, M. M. & Joule, J. A. (2010). Acta Cryst. E66, o112.], 2012[Helliwell, M., Baradarani, M. M., Mohammadnejadaghdam, R., Afghan, A., & Joule, J. A. (2012). Acta Cryst. E68, o233.]). For graph-set notation, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C14H14ClN3O

  • Mr = 275.73

  • Triclinic, [P \overline 1]

  • a = 8.226 (2) Å

  • b = 9.282 (3) Å

  • c = 9.744 (3) Å

  • α = 92.124 (5)°

  • β = 104.766 (5)°

  • γ = 105.294 (4)°

  • V = 689.5 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 100 K

  • 0.58 × 0.22 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 3384 measured reflections

  • 2389 independent reflections

  • 1549 reflections with I > 2σ(I)

  • Rint = 0.065
Refinement

  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.132

  • S = 1.01

  • 2389 reflections

  • 187 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.93 (5) 1.89 (5) 2.610 (4) 132 (4)
N3—H3M⋯O1i 0.83 (5) 2.11 (5) 2.931 (5) 176 (5)
N3—H3N⋯N2ii 0.85 (4) 2.24 (4) 3.065 (5) 163 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053918/pk2373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053918/pk2373Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053918/pk2373Isup3.cml

checkCIF report


Comment top

We showed that the interaction of 2,3,3-trimethyl-3H-indoles with the Vilsmeier reagent produces (1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)propanedials (Baradarani et al., 2006). 2,3,3-Trimethyl-2H-pyrrolo[2,3-f]quinoline, 2,3,3-trimethyl-3H-pyrrolo[3,2-h]quinoline (Rashidi et al., 2009), 2,2',3,3,3',3'-hexamethyl-3H,3'H-5,5'-biindole and 2,3,3,7,8,8-hexamethyl-3H,8H-indolo[7,6-g]indole (Rashidi et al., 2011) behave analogously. The (1,3-dihydroindol-2-ylidene)propanedials were shown to react with arylhydrazines (or hydrazine) to produce 3,3-dimethyl-2-[1-aryl-1H-pyrazol-4-yl]-3H-indoles (Baradarani et al., 2006. Rashidi et al., 2009. Helliwell et al. 2010. Rashidi et al., 2011).

In anticipation that the (1,3-dihydroindol-2-ylidene)propanedials would react with hydroxylamine to produce isoxazol-4-yl-3H-indoles, 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2H-indol-2-ylidene)propanedial was treated with hydroxylamine in refluxing ethanol. The unexpected product of the reaction was 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2H-indol-2-ylidene)-2- cyanoacetamide as shown by this X-ray analysis (Fig. 1).

We interpret this transformation as involving firstly formation of the diooxime 1 which cyclizes to generate aminal 2, loss of water would then produce imine 3, proton-induced fragmentation of which (arrows on 3) would then lead to the product 4 (Fig. 2).

The sum of the angles of the bonds at the ring nitrogen in 4 is 361 (4)° showing the extensive conjugation of the nitrogen with the 2-cyanoacrylamide subunit. The geometry of the double bond linking the heterocyclic and cyanoacetamide subunits is E.

The orientation of the acetamide group arises from intramolecular H bonding between the indole N—H and the carbonyl group. The inversion related acetamide groups form N—H···O hydrogen bonded dimers in graph-set R22(8) motifs (Etter et al., 1990), while dimers are also formed by pairs of N—H(amine)···N(nitrile) functionalities in R22(12) motifs. These interactions together generate ribbons that propagate along the b axis direction (Fig. 3).

Related literature top

For background information on the chemistry of related compounds, see: Baradarani et al. (2006); Rashidi et al. (2009, 2011). For related structures, see; Helliwell et al. (2010, 2012). For graph-set notation, see: Etter et al. (1990).

Experimental top

A mixture of 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2H-indol-2-ylidene)propanedial (100 mg, 0.38 mmol) and hydroxylamine hydrochloride (52 mg, 0.76 mmol) in absolute EtOH (10 ml) was heated with stirring at reflux for 7 h. After complete conversion, the reaction mixture was cooled and concentrated, and the resulting crystals were collected by filtration and recrystallized from EtOH to give the 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2H-indol-2-ylidene)-2-cyanoacrylamide (90 mg, 86%), 522–524 K, FT—IR (KBr) νmax 3385, 3289, 3185, 2986, 2939, 2199, 1668, 1608, 1563, 1415, 1329, 909, 788 cm-1, 1H NMR (CDCl3) δ 1.84 (s, 6H, 2CH3), 2.30 (s, 3H, CH3), 5.20–6.50 (bs, 2H, NH2), 6.93 (d, J = 8.1 Hz, 1H, ArH), 7.00 (d, J = 8.1 Hz, 1H, ArH), 11.85 (bs, 1H, NH), 13C NMR (CDCl3) δ 15.9, 21.0, 51.6, 118.9, 118.9, 124.9, 127.4, 130.8, 132.5, 141.0, 169.6,177.4.

Refinement top

H atoms bonded to C were included in calculated positions using the riding method, with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and C—H distances of 0.95 Å and Uiso(H) = 1.2Ueq(C) for the aromatic H atoms. Those bonded to N were found by difference Fourier methods and refined isotropically with the N—H distances ranging from to 0.83 (5) to 0.93 (5) Å.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A plot of the title compound with ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Synthesis of 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl -2H-indol-2-ylidene)-2-cyanoacetamide
[Figure 3] Fig. 3. Packing arrangement of the title compound showing the H bonding which links the molecules into chains parallel to b. Only those H atoms that are involved in H bonding are shown for clarity.
2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2- cyanoacetamide top
Crystal data top
C14H14ClN3OZ = 2
Mr = 275.73F(000) = 288
Triclinic, P1Dx = 1.328 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.226 (2) ÅCell parameters from 735 reflections
b = 9.282 (3) Åθ = 2.7–25.8°
c = 9.744 (3) ŵ = 0.27 mm−1
α = 92.124 (5)°T = 100 K
β = 104.766 (5)°Plate, colourless
γ = 105.294 (4)°0.58 × 0.22 × 0.10 mm
V = 689.5 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		1549 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ϕ and ω scansh = −9→9
3384 measured reflectionsk = −10→11
2389 independent reflectionsl = −10→11
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0419P)2]
where P = (Fo2 + 2Fc2)/3
2389 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C14H14ClN3Oγ = 105.294 (4)°
Mr = 275.73V = 689.5 (3) Å3
Triclinic, P1Z = 2
a = 8.226 (2) ÅMo Kα radiation
b = 9.282 (3) ŵ = 0.27 mm−1
c = 9.744 (3) ÅT = 100 K
α = 92.124 (5)°0.58 × 0.22 × 0.10 mm
β = 104.766 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1549 reflections with I > 2σ(I)
3384 measured reflectionsRint = 0.065
2389 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.45 e Å−3
2389 reflectionsΔρmin = −0.38 e Å−3
187 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 > σ(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
xyzUiso*/Ueq
Cl1−0.29616 (14)0.79125 (12)0.38519 (11)0.0274 (3)
O10.3245 (3)0.4944 (3)0.0925 (3)0.0224 (7)
N10.0818 (4)0.5294 (4)0.2080 (3)0.0190 (8)
H1N0.140 (6)0.464 (6)0.181 (5)0.064 (17)*
N20.3940 (5)1.0145 (4)0.1147 (4)0.0306 (9)
N30.4858 (5)0.6920 (5)0.0127 (4)0.0225 (8)
H3N0.517 (5)0.783 (5)−0.006 (4)0.022 (12)*
H3M0.539 (7)0.637 (6)−0.013 (5)0.061 (18)*
C1−0.0620 (5)0.4992 (4)0.2658 (4)0.0182 (9)
C2−0.1558 (5)0.3606 (5)0.2912 (4)0.0207 (9)
C3−0.2983 (5)0.3602 (5)0.3433 (4)0.0244 (10)
H3−0.36930.26730.35980.029*
C4−0.3399 (5)0.4911 (5)0.3718 (4)0.0241 (10)
H4−0.43700.48780.40870.029*
C5−0.2383 (5)0.6280 (5)0.3461 (4)0.0218 (10)
C6−0.0984 (5)0.6349 (4)0.2903 (4)0.0179 (9)
C70.0298 (5)0.7621 (4)0.2452 (4)0.0174 (9)
C80.1405 (5)0.6759 (4)0.1913 (4)0.0194 (9)
C9−0.1084 (5)0.2188 (4)0.2602 (5)0.0271 (10)
H9A−0.08650.21710.16600.041*
H9B−0.20530.13120.26130.041*
H9C−0.00270.21610.33320.041*
C10−0.0645 (5)0.8363 (4)0.1230 (4)0.0233 (10)
H10A0.02180.91690.09620.035*
H10B−0.14810.87840.15460.035*
H10C−0.12740.76100.04030.035*
C110.1435 (5)0.8796 (5)0.3722 (4)0.0262 (10)
H11A0.20780.83070.44600.039*
H11B0.06810.92530.41170.039*
H11C0.22680.95770.33970.039*
C120.2765 (5)0.7319 (4)0.1318 (4)0.0183 (9)
C130.3378 (5)0.8890 (5)0.1241 (4)0.0216 (10)
C140.3650 (5)0.6315 (4)0.0777 (4)0.0174 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0283 (6)0.0262 (7)0.0351 (7)0.0153 (5)0.0142 (5)0.0008 (5)
O10.0237 (16)0.0140 (17)0.0356 (18)0.0083 (12)0.0150 (13)0.0072 (13)
N10.0193 (19)0.015 (2)0.027 (2)0.0076 (15)0.0104 (16)0.0061 (15)
N20.031 (2)0.019 (2)0.048 (2)0.0074 (18)0.0209 (19)0.0073 (19)
N30.023 (2)0.015 (2)0.035 (2)0.0071 (17)0.0143 (17)0.0068 (18)
C10.015 (2)0.024 (2)0.020 (2)0.0082 (18)0.0094 (18)0.0058 (18)
C20.020 (2)0.022 (2)0.022 (2)0.0093 (19)0.0067 (18)0.0052 (18)
C30.026 (2)0.022 (2)0.028 (2)0.0052 (19)0.012 (2)0.0083 (19)
C40.017 (2)0.033 (3)0.025 (2)0.007 (2)0.0097 (19)0.004 (2)
C50.024 (2)0.021 (2)0.024 (2)0.0132 (19)0.0052 (19)0.0006 (19)
C60.017 (2)0.020 (2)0.019 (2)0.0095 (18)0.0057 (18)0.0044 (18)
C70.014 (2)0.018 (2)0.024 (2)0.0087 (17)0.0070 (18)0.0033 (18)
C80.020 (2)0.017 (2)0.021 (2)0.0086 (18)0.0017 (18)0.0054 (18)
C90.030 (3)0.018 (2)0.037 (3)0.007 (2)0.015 (2)0.009 (2)
C100.021 (2)0.019 (2)0.032 (3)0.0074 (18)0.0093 (19)0.0061 (19)
C110.028 (3)0.026 (3)0.026 (2)0.012 (2)0.0059 (19)0.000 (2)
C120.019 (2)0.013 (2)0.026 (2)0.0092 (17)0.0069 (18)0.0057 (18)
C130.017 (2)0.022 (3)0.031 (2)0.0081 (19)0.0137 (19)0.004 (2)
C140.016 (2)0.016 (2)0.021 (2)0.0073 (17)0.0013 (18)0.0027 (18)
Geometric parameters (Å, º) top
Cl1—C51.760 (4)C5—C61.381 (5)
O1—C141.251 (4)C6—C71.523 (5)
N1—C81.349 (5)C7—C81.531 (5)
N1—C11.404 (4)C7—C111.538 (5)
N1—H1N0.93 (5)C7—C101.538 (5)
N2—C131.151 (5)C8—C121.380 (5)
N3—C141.326 (5)C9—H9A0.9800
N3—H3N0.85 (4)C9—H9B0.9800
N3—H3M0.83 (5)C9—H9C0.9800
C1—C21.381 (5)C10—H10A0.9800
C1—C61.395 (5)C10—H10B0.9800
C2—C31.391 (5)C10—H10C0.9800
C2—C91.509 (5)C11—H11A0.9800
C3—C41.383 (5)C11—H11B0.9800
C3—H30.9500C11—H11C0.9800
C4—C51.395 (5)C12—C131.424 (5)
C4—H40.9500C12—C141.481 (5)
C8—N1—C1112.7 (3)C11—C7—C10111.0 (3)
C8—N1—H1N118 (3)N1—C8—C12123.4 (3)
C1—N1—H1N130 (3)N1—C8—C7108.8 (3)
C14—N3—H3N128 (3)C12—C8—C7127.8 (4)
C14—N3—H3M118 (3)C2—C9—H9A109.5
H3N—N3—H3M114 (4)C2—C9—H9B109.5
C2—C1—C6125.2 (3)H9A—C9—H9B109.5
C2—C1—N1127.0 (3)C2—C9—H9C109.5
C6—C1—N1107.8 (3)H9A—C9—H9C109.5
C1—C2—C3115.8 (4)H9B—C9—H9C109.5
C1—C2—C9121.7 (3)C7—C10—H10A109.5
C3—C2—C9122.5 (4)C7—C10—H10B109.5
C4—C3—C2121.9 (4)H10A—C10—H10B109.5
C4—C3—H3119.0C7—C10—H10C109.5
C2—C3—H3119.0H10A—C10—H10C109.5
C3—C4—C5119.6 (3)H10B—C10—H10C109.5
C3—C4—H4120.2C7—C11—H11A109.5
C5—C4—H4120.2C7—C11—H11B109.5
C6—C5—C4121.1 (4)H11A—C11—H11B109.5
C6—C5—Cl1121.2 (3)C7—C11—H11C109.5
C4—C5—Cl1117.7 (3)H11A—C11—H11C109.5
C5—C6—C1116.4 (4)H11B—C11—H11C109.5
C5—C6—C7133.7 (4)C8—C12—C13120.4 (3)
C1—C6—C7109.9 (3)C8—C12—C14121.2 (3)
C6—C7—C8100.8 (3)C13—C12—C14118.4 (3)
C6—C7—C11111.8 (3)N2—C13—C12176.3 (4)
C8—C7—C11110.9 (3)O1—C14—N3122.0 (4)
C6—C7—C10111.6 (3)O1—C14—C12120.4 (3)
C8—C7—C10110.2 (3)N3—C14—C12117.6 (4)
C8—N1—C1—C2177.6 (4)C5—C6—C7—C1163.5 (6)
C8—N1—C1—C6−0.8 (4)C1—C6—C7—C11−117.4 (4)
C6—C1—C2—C31.0 (6)C5—C6—C7—C10−61.6 (6)
N1—C1—C2—C3−177.1 (4)C1—C6—C7—C10117.5 (4)
C6—C1—C2—C9179.4 (4)C1—N1—C8—C12−177.6 (4)
N1—C1—C2—C91.2 (6)C1—N1—C8—C71.1 (4)
C1—C2—C3—C4−1.9 (6)C6—C7—C8—N1−1.0 (4)
C9—C2—C3—C4179.7 (4)C11—C7—C8—N1117.6 (4)
C2—C3—C4—C50.9 (6)C10—C7—C8—N1−119.0 (4)
C3—C4—C5—C61.1 (6)C6—C7—C8—C12177.7 (4)
C3—C4—C5—Cl1−179.6 (3)C11—C7—C8—C12−63.7 (5)
C4—C5—C6—C1−2.0 (6)C10—C7—C8—C1259.7 (5)
Cl1—C5—C6—C1178.8 (3)N1—C8—C12—C13−176.7 (4)
C4—C5—C6—C7177.0 (4)C7—C8—C12—C134.7 (6)
Cl1—C5—C6—C7−2.2 (6)N1—C8—C12—C141.8 (6)
C2—C1—C6—C50.9 (6)C7—C8—C12—C14−176.7 (4)
N1—C1—C6—C5179.3 (3)C8—C12—C14—O1−4.2 (6)
C2—C1—C6—C7−178.3 (4)C13—C12—C14—O1174.4 (4)
N1—C1—C6—C70.1 (4)C8—C12—C14—N3175.2 (4)
C5—C6—C7—C8−178.5 (4)C13—C12—C14—N3−6.2 (6)
C1—C6—C7—C80.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.93 (5)1.89 (5)2.610 (4)132 (4)
N3—H3M···O1i0.83 (5)2.11 (5)2.931 (5)176 (5)
N3—H3N···N2ii0.85 (4)2.24 (4)3.065 (5)163 (3)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC14H14ClN3O
Mr275.73
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.226 (2), 9.282 (3), 9.744 (3)
α, β, γ (°)92.124 (5), 104.766 (5), 105.294 (4)
V (Å3)689.5 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.58 × 0.22 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		3384, 2389, 1549
Rint0.065
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.132, 1.01
No. of reflections2389
No. of parameters187
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.38

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.93 (5)1.89 (5)2.610 (4)132 (4)
N3—H3M···O1i0.83 (5)2.11 (5)2.931 (5)176 (5)
N3—H3N···N2ii0.85 (4)2.24 (4)3.065 (5)163 (3)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z.
 

Acknowledgements

The authors are grateful to the University of Urmia for financial support of this work.

References

First citationBaradarani, M. M., Afghan, A., Zebarjadi, F., Hasanzadeh, K. & Joule, J. A. (2006). J. Heterocycl. Chem. 43, 1591–1596.  CrossRef CAS Google Scholar
 First citationBruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationHelliwell, M., Afghan, A., Keshvari, F., Baradarani, M. M. & Joule, J. A. (2010). Acta Cryst. E66, o112.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHelliwell, M., Baradarani, M. M., Mohammadnejadaghdam, R., Afghan, A., & Joule, J. A. (2012). Acta Cryst. E68, o233.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428–431.  Web of Science CrossRef CAS Google Scholar
 First citationRashidi, A., Baradarani, M. M. & Joule, J. A. (2011). Arkivoc, ii, 252–259.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 1| January 2012| Page o234
doi:10.1107/S1600536811053918
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