(2E)-2-[(3E)-4-Phenyl­but-3-en-2-yl­idene]hydrazinecarboxamide

Samshuddin, S.; Butcher, R.J.; Yıldırım, S.O.; Akkurt, M.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S160053681105255X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o76-o77

doi:10.1107/S160053681105255X

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(2E)-2-[(3E)-4-Phenylbut-3-en-2-ylidene]hydrazinecarboxamide

S. Samshuddin,^a Ray J. Butcher,^b Sema Ozturk Yıldırım,^c Mehmet Akkurt,^d ^* B. Narayana ^a and H. S. Yathirajan ^e

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and, Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 5 December 2011; accepted 6 December 2011; online 10 December 2011)

In the title compound, C₁₁H₁₃N₃O, the phenyl ring is disordered over two sites, with occupancy factors in a 0.520 (17):0.480 (17) ratio. The dihedral angle between the ring planes of the major and minor components of the disordered ring is 12.9 (2)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming R₂²(8) ring motifs. C—H⋯O, C—H⋯N and C—H⋯π interactions also occur.

Related literature

For background to the biological activity of semicarbazones, see: Beraldo et al. (2002 ); Teixeira et al. (2003 ); Du et al. (2004 ); Kucukguzel et al. (2006 ); Beraldo & Gambino (2004 ). For related structures, see: Naik & Palenik (1974 ); Wang et al. (2004 ); Yathirajan et al. (2006 ); Sarojini et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₃N₃O
M_r = 203.24
Monoclinic, C 2/c
a = 15.1094 (8) Å
b = 24.4445 (11) Å
c = 7.0368 (4) Å
β = 109.908 (6)°
V = 2443.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 123 K
0.40 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.987, T_max = 1.000
12712 measured reflections
3528 independent reflections
2748 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.176
S = 1.05
3528 reflections
168 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A –C6A and C1B–C6B, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1ⁱ	0.88	2.12	2.9785 (15)	166
N3—H3B⋯O1ⁱⁱ	0.88	2.08	2.9434 (14)	168
C10—H10A⋯O1ⁱ	0.98	2.51	3.2384 (17)	131
C10—H10B⋯N1ⁱⁱⁱ	0.98	2.58	3.4566 (19)	148
C4B—H4BA⋯Cg1^iv	0.95	2.86	3.618 (5)	138
C4A—H4AA⋯Cg1^iv	0.95	2.76	3.590 (5)	146
C4A—H4AA⋯Cg2^iv	0.95	2.93	3.714 (5)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+3]$ ; (ii) $[-x+1, y, -z+{\script{7\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105255X/tk5032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105255X/tk5032Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105255X/tk5032Isup3.cml

checkCIF report

Comment top

Semicarbazones presents a wide range of biological applications such as antitumoral, anticonvulsant, anti-trypanosomal, herbicidal and biocidal activities (Beraldo & Gambino, 2004; Beraldo et al., 2002; Teixeira et al., 2003). They can also be used as important intermediates in organic synthesis, mainly for obtaining heterocycle rings, such as thiazolidones, oxadiazoles, pyrazolidones, and thiadiazoles (Du et al., 2004; Kucukguzel et al., 2006)

Crystal structures of some semicarbazone derivatives, viz., acetone semicarbazone and benzaldehyde semicarbazone (Naik & Palenik, 1974); 3,4- methylenedioxybenzaldehyde semicarbazone (Wang et al.,2004); 4-(methylsulfanyl)benzaldehyde thiosemicarbazone (Yathirajan et al., 2006) and 4-(Methylsulfanyl)benzaldehyde semicarbazone (Sarojini et al., 2007) have been reported. In view of the importance of semicarbazones, the title compound (I) was prepared and its crystal structure is reported.

Fig. 1 shows the molecular structure of the title compound (I) with the disordered phenyl ring. The dihedral angle between the major and minor disorder components of the phenyl ring is 12.9 (2)°. The C7—C8—C9—C10, C7—C8—C9—N1, C10—C9—N1—N2, C8—C9—N1—N2, N1—N2—C11—N3 and N1—N2—C11—O1 torsion angles are -2.7 (2), 178.13 (13), -1.37 (19), 179.53 (10), -1.40 (17) and 179.22 (11)°, respectively, and indicate planarity in the molecule.

In the crystal, the molecules form centrosymmetric dimers with an R₂²(8) ring motif through a pair of N—H···O hydrogen bonds. These dimers are further connected into a three-dimensional network by intermolecular C—H···O and C—H···N hydrogen bonds (Table 1, Fig. 2). Weak intermolecular C—H···π interactions further stabilize the crystal structure.

Related literature top

For background to the biological activity of semicarbazones, see: Beraldo et al. (2002); Teixeira et al. (2003); Du et al. (2004); Kucukguzel et al. (2006); Beraldo & Gambino (2004). For related structures, see: Naik & Palenik (1974); Wang et al. (2004); Yathirajan et al. (2006); Sarojini et al. (2007).

Experimental top

To a mixture of a benzylidene acetone (1.46 g, 0.01 mol) and semicarbazide hydrochloride (1.12 g, 0.01 mol) in 50 ml ethanol was added a sodium acetate solution (2 g in 5 ml water) which was then refluxed for 4 h. The resultant solution was concentrated to half of its volume and poured into 50 ml ice-cold water. The precipitate thus formed was collected by filtration and purified by recrystallization from ethanol. The single crystal was grown from its absolute alcohol solution by slow evaporation. The yield was 74%. (M.pt. 455–459 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The disordered molecule (I) showing the atom labeling scheme. Atoms of the minor disorder components are joined with dashed lines. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the N—H···O mediated dimers in (I) and their connections to other molecules by C—H···O and C—H···O hydrogen bonding.

(2E)-2-[(3E)-4-Phenylbut-3-en-2-ylidene]hydrazinecarboxamide top

Crystal data top

C₁₁H₁₃N₃O	F(000) = 864
M_r = 203.24	D_x = 1.105 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5469 reflections
a = 15.1094 (8) Å	θ = 3.0–30.9°
b = 24.4445 (11) Å	µ = 0.07 mm⁻¹
c = 7.0368 (4) Å	T = 123 K
β = 109.908 (6)°	Prism, colourless
V = 2443.7 (2) Å³	0.40 × 0.30 × 0.18 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3528 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.5081 pixels mm^-1	θ_max = 30.9°, θ_min = 3.0°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −34→26
T_min = 0.987, T_max = 1.000	l = −7→9
12712 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0981P)² + 0.6768P] where P = (F_o² + 2F_c²)/3
3528 reflections	(Δ/σ)_max < 0.001
168 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₁H₁₃N₃O	V = 2443.7 (2) Å³
M_r = 203.24	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.1094 (8) Å	µ = 0.07 mm⁻¹
b = 24.4445 (11) Å	T = 123 K
c = 7.0368 (4) Å	0.40 × 0.30 × 0.18 mm
β = 109.908 (6)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3528 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2748 reflections with I > 2σ(I)
T_min = 0.987, T_max = 1.000	R_int = 0.026
12712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
3528 reflections	Δρ_min = −0.22 e Å⁻³
168 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.36888 (6)	0.23438 (4)	1.62948 (12)	0.0323 (3)
N1	0.34428 (7)	0.30220 (5)	1.17621 (15)	0.0337 (3)
N2	0.31934 (7)	0.27704 (4)	1.32596 (14)	0.0310 (3)
N3	0.47771 (7)	0.26174 (6)	1.49376 (16)	0.0458 (4)
C1B	0.3063 (5)	0.40506 (19)	0.5724 (7)	0.0301 (9)	0.520 (17)
C2B	0.2428 (5)	0.4316 (2)	0.4074 (6)	0.0354 (10)	0.520 (17)
C3B	0.2747 (6)	0.45824 (19)	0.2685 (6)	0.0405 (13)	0.520 (17)
C4B	0.3701 (6)	0.45829 (14)	0.2947 (8)	0.0409 (13)	0.520 (17)
C5B	0.4336 (6)	0.4317 (2)	0.4598 (11)	0.0469 (14)	0.520 (17)
C6B	0.4017 (5)	0.4051 (2)	0.5986 (11)	0.0434 (11)	0.520 (17)
C7	0.25908 (11)	0.37670 (5)	0.71144 (19)	0.0393 (4)
C8	0.31231 (10)	0.35103 (5)	0.87866 (19)	0.0375 (4)
C9	0.27918 (9)	0.32596 (5)	1.03065 (18)	0.0327 (3)
C10	0.17796 (10)	0.32953 (6)	1.0129 (2)	0.0395 (4)
C11	0.38883 (8)	0.25686 (5)	1.49014 (17)	0.0304 (3)
C3A	0.2443 (5)	0.4630 (2)	0.2639 (7)	0.0458 (13)	0.480 (17)
C4A	0.3345 (6)	0.45553 (15)	0.2576 (7)	0.0378 (13)	0.480 (17)
C5A	0.3972 (6)	0.4208 (2)	0.3956 (10)	0.0408 (14)	0.480 (17)
C6A	0.3697 (5)	0.39363 (19)	0.5398 (9)	0.0337 (11)	0.480 (17)
C2A	0.2169 (4)	0.4358 (2)	0.4081 (7)	0.0402 (11)	0.480 (17)
C1A	0.2795 (4)	0.40110 (19)	0.5461 (6)	0.0276 (10)	0.480 (17)
H7A	0.19470	0.37930	0.69980	0.0470*
H3BA	0.23130	0.47640	0.15570	0.0490*	0.520 (17)
H5BA	0.49890	0.43180	0.47770	0.0560*	0.520 (17)
H6BA	0.44510	0.38700	0.71150	0.0520*	0.520 (17)
H10A	0.17330	0.33360	1.14770	0.0590*
H10B	0.14520	0.29610	0.94940	0.0590*
H10C	0.14890	0.36120	0.92980	0.0590*
H4BA	0.39200	0.47650	0.19980	0.0490*	0.520 (17)
H8A	0.37790	0.34890	0.90100	0.0450*
H2B	0.25980	0.27410	1.31570	0.0370*
H3B	0.52440	0.24890	1.59690	0.0550*
H3C	0.48940	0.27780	1.39300	0.0550*
H2BA	0.17760	0.43160	0.38950	0.0420*	0.520 (17)
H2AA	0.15520	0.44090	0.41240	0.0480*	0.480 (17)
H3AA	0.20150	0.48670	0.16960	0.0550*	0.480 (17)
H4AA	0.35330	0.47410	0.15910	0.0450*	0.480 (17)
H5AA	0.45880	0.41570	0.39130	0.0490*	0.480 (17)
H6AA	0.41250	0.36990	0.63410	0.0400*	0.480 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0234 (4)	0.0505 (6)	0.0224 (4)	0.0004 (3)	0.0069 (3)	0.0096 (3)
N1	0.0334 (5)	0.0409 (6)	0.0276 (5)	−0.0035 (4)	0.0113 (4)	0.0100 (4)
N2	0.0239 (4)	0.0438 (6)	0.0243 (5)	−0.0019 (4)	0.0069 (4)	0.0107 (4)
N3	0.0224 (5)	0.0857 (10)	0.0292 (5)	−0.0024 (5)	0.0086 (4)	0.0155 (5)
C1B	0.045 (2)	0.0227 (15)	0.0208 (13)	0.0012 (14)	0.0088 (15)	0.0032 (10)
C2B	0.045 (2)	0.0379 (17)	0.0259 (14)	0.0056 (16)	0.0156 (14)	0.0043 (11)
C3B	0.059 (3)	0.0386 (18)	0.0276 (14)	0.0065 (18)	0.0197 (17)	0.0131 (11)
C4B	0.065 (3)	0.0320 (15)	0.0343 (18)	−0.0086 (16)	0.028 (2)	0.0002 (13)
C5B	0.055 (3)	0.0457 (19)	0.050 (2)	−0.0018 (19)	0.031 (2)	0.0083 (17)
C6B	0.046 (2)	0.0458 (19)	0.041 (2)	0.0010 (18)	0.0182 (19)	0.0113 (17)
C7	0.0638 (9)	0.0303 (6)	0.0298 (6)	0.0083 (6)	0.0238 (6)	0.0061 (5)
C8	0.0488 (7)	0.0349 (6)	0.0335 (6)	0.0037 (5)	0.0202 (6)	0.0097 (5)
C9	0.0389 (6)	0.0323 (6)	0.0279 (5)	0.0005 (5)	0.0126 (5)	0.0065 (4)
C10	0.0397 (7)	0.0478 (8)	0.0320 (6)	0.0081 (5)	0.0135 (5)	0.0127 (5)
C11	0.0240 (5)	0.0424 (7)	0.0238 (5)	−0.0017 (4)	0.0067 (4)	0.0040 (4)
C3A	0.056 (3)	0.044 (2)	0.0397 (18)	0.0139 (18)	0.0194 (18)	0.0134 (14)
C4A	0.055 (3)	0.0314 (17)	0.0291 (15)	−0.0016 (18)	0.017 (2)	0.0062 (12)
C5A	0.045 (3)	0.0402 (19)	0.044 (2)	0.0033 (16)	0.024 (2)	0.0081 (16)
C6A	0.038 (2)	0.0309 (16)	0.0338 (19)	0.0064 (14)	0.0144 (18)	0.0112 (13)
C2A	0.053 (2)	0.0369 (19)	0.0353 (17)	0.0087 (17)	0.0212 (16)	0.0099 (13)
C1A	0.038 (2)	0.0219 (14)	0.0268 (15)	−0.0032 (14)	0.0161 (14)	−0.0043 (12)

Geometric parameters (Å, º) top

O1—C11	1.2472 (15)	C5A—C6A	1.389 (10)
N1—N2	1.3788 (15)	C5B—C6B	1.389 (10)
N1—C9	1.2915 (17)	C7—C8	1.3344 (18)
N2—C11	1.3618 (15)	C8—C9	1.4610 (19)
N3—C11	1.3398 (17)	C9—C10	1.494 (2)
N2—H2B	0.8800	C2A—H2AA	0.9500
N3—H3B	0.8800	C2B—H2BA	0.9500
N3—H3C	0.8800	C3A—H3AA	0.9500
C1A—C7	1.432 (5)	C3B—H3BA	0.9500
C1A—C6A	1.391 (10)	C4A—H4AA	0.9500
C1A—C2A	1.390 (7)	C4B—H4BA	0.9500
C1B—C2B	1.390 (7)	C5A—H5AA	0.9500
C1B—C6B	1.390 (11)	C5B—H5BA	0.9500
C1B—C7	1.556 (6)	C6A—H6AA	0.9500
C2A—C3A	1.389 (8)	C6B—H6BA	0.9500
C2B—C3B	1.390 (9)	C7—H7A	0.9500
C3A—C4A	1.391 (12)	C8—H8A	0.9500
C3B—C4B	1.390 (13)	C10—H10B	0.9800
C4A—C5A	1.391 (9)	C10—H10C	0.9800
C4B—C5B	1.391 (9)	C10—H10A	0.9800

N2—N1—C9	118.31 (11)	C3A—C2A—H2AA	120.00
N1—N2—C11	118.53 (11)	C1A—C2A—H2AA	120.00
N1—N2—H2B	121.00	C3B—C2B—H2BA	120.00
C11—N2—H2B	121.00	C1B—C2B—H2BA	120.00
C11—N3—H3B	120.00	C4A—C3A—H3AA	120.00
H3B—N3—H3C	120.00	C2A—C3A—H3AA	120.00
C11—N3—H3C	120.00	C4B—C3B—H3BA	120.00
C6A—C1A—C7	117.1 (4)	C2B—C3B—H3BA	120.00
C2A—C1A—C7	122.6 (5)	C5A—C4A—H4AA	120.00
C2A—C1A—C6A	119.9 (5)	C3A—C4A—H4AA	120.00
C2B—C1B—C7	113.5 (6)	C5B—C4B—H4BA	120.00
C2B—C1B—C6B	120.0 (6)	C3B—C4B—H4BA	120.00
C6B—C1B—C7	126.4 (5)	C4A—C5A—H5AA	120.00
C1A—C2A—C3A	120.1 (6)	C6A—C5A—H5AA	120.00
C1B—C2B—C3B	120.0 (7)	C4B—C5B—H5BA	120.00
C2A—C3A—C4A	120.0 (5)	C6B—C5B—H5BA	120.00
C2B—C3B—C4B	120.0 (5)	C5A—C6A—H6AA	120.00
C3A—C4A—C5A	120.0 (6)	C1A—C6A—H6AA	120.00
C3B—C4B—C5B	120.0 (6)	C5B—C6B—H6BA	120.00
C4A—C5A—C6A	120.0 (8)	C1B—C6B—H6BA	120.00
C4B—C5B—C6B	120.0 (8)	C1A—C7—H7A	114.00
C1A—C6A—C5A	120.0 (6)	C1B—C7—H7A	126.00
C1B—C6B—C5B	120.0 (6)	C8—C7—H7A	114.00
C1B—C7—C8	119.7 (3)	C9—C8—H8A	117.00
C1A—C7—C8	132.9 (3)	C7—C8—H8A	117.00
C7—C8—C9	126.08 (15)	C9—C10—H10C	110.00
N1—C9—C8	114.27 (13)	C9—C10—H10B	109.00
C8—C9—C10	120.69 (11)	H10B—C10—H10C	109.00
N1—C9—C10	125.04 (12)	H10A—C10—H10B	110.00
N2—C11—N3	117.53 (11)	H10A—C10—H10C	109.00
O1—C11—N3	122.23 (11)	C9—C10—H10A	110.00
O1—C11—N2	120.24 (12)

C9—N1—N2—C11	−173.34 (11)	C2B—C1B—C7—C8	−178.1 (3)
N2—N1—C9—C8	−179.53 (10)	C6B—C1B—C7—C8	2.8 (6)
N2—N1—C9—C10	1.37 (19)	C1B—C2B—C3B—C4B	0.0 (7)
N1—N2—C11—O1	179.22 (11)	C2B—C3B—C4B—C5B	0.0 (7)
N1—N2—C11—N3	−1.40 (17)	C3B—C4B—C5B—C6B	0.0 (8)
C6B—C1B—C2B—C3B	0.0 (7)	C4B—C5B—C6B—C1B	0.0 (8)
C7—C1B—C2B—C3B	−179.2 (4)	C1B—C7—C8—C9	175.5 (2)
C2B—C1B—C6B—C5B	0.0 (8)	C7—C8—C9—N1	178.13 (13)
C7—C1B—C6B—C5B	179.1 (4)	C7—C8—C9—C10	−2.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A –C6A and C1B–C6B, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.88	2.12	2.9785 (15)	166
N3—H3B···O1ⁱⁱ	0.88	2.08	2.9434 (14)	168
N3—H3C···N1	0.88	2.28	2.6397 (16)	104
C10—H10A···O1ⁱ	0.98	2.51	3.2384 (17)	131
C10—H10B···N1ⁱⁱⁱ	0.98	2.58	3.4566 (19)	148
C4B—H4BA···Cg1^iv	0.95	2.86	3.618 (5)	138
C4A—H4AA···Cg1^iv	0.95	2.76	3.590 (5)	146
C4A—H4AA···Cg2^iv	0.95	2.93	3.714 (5)	141

Symmetry codes: (i) −x+1/2, −y+1/2, −z+3; (ii) −x+1, y, −z+7/2; (iii) −x+1/2, −y+1/2, −z+2; (iv) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₃O
M_r	203.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	15.1094 (8), 24.4445 (11), 7.0368 (4)
β (°)	109.908 (6)
V (Å³)	2443.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.30 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.987, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12712, 3528, 2748
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.723

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.176, 1.05
No. of reflections	3528
No. of parameters	168
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A –C6A and C1B–C6B, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.88	2.12	2.9785 (15)	166
N3—H3B···O1ⁱⁱ	0.88	2.08	2.9434 (14)	168
C10—H10A···O1ⁱ	0.98	2.51	3.2384 (17)	131
C10—H10B···N1ⁱⁱⁱ	0.98	2.58	3.4566 (19)	148
C4B—H4BA···Cg1^iv	0.95	2.86	3.618 (5)	138
C4A—H4AA···Cg1^iv	0.95	2.76	3.590 (5)	146
C4A—H4AA···Cg2^iv	0.95	2.93	3.714 (5)	141

Symmetry codes: (i) −x+1/2, −y+1/2, −z+3; (ii) −x+1, y, −z+7/2; (iii) −x+1/2, −y+1/2, −z+2; (iv) x, −y+1, z−1/2.

Acknowledgements

BN thanks the UGC for financial assistance through SAP and BSR one-time grants for the purchase of chemicals. HSY thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

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Volume 68| Part 1| January 2012| Pages o76-o77

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