N′-(3-Phenyl­allyl­idene)isonicotino­hydrazide

Bao, F.-Y.

doi:10.1107/S1600536808026287

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1789

doi:10.1107/S1600536808026287

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N′-(3-Phenylallylidene)isonicotinohydrazide

Feng-Yu Bao ^a ^*

^aDepartment of Applied Chemistry, College of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: bfyu2008@yahoo.com.cn

(Received 3 July 2008; accepted 14 August 2008; online 20 August 2008)

The asymmetric unit of the title compound, C₁₅H₁₃N₃O, contains two similar molecules. Each molecule is non-planar, as indicated by the dihedral angles between the pyridine and benzene rings of 45.2 (2) and 56.6 (2)°. The crystal structure is consolidated by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Kahwa et al. (1986 ); Qian et al. (2006 ); Santos et al. (2001 ).

Experimental

Crystal data

C₁₅H₁₃N₃O
M_r = 251.28
Monoclinic, P c
a = 12.608 (8) Å
b = 11.023 (7) Å
c = 10.044 (7) Å
β = 105.94 (3)°
V = 1342.2 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.98, T_max = 0.98
11645 measured reflections
3110 independent reflections
2784 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.134
S = 1.01
3110 reflections
349 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86 (5)	2.19 (5)	3.050 (6)	174 (3)
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026287/ez2136sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026287/ez2136Isup2.hkl

checkCIF report

Comment top

Interest in the chemistry of Schiff bases has increased considerably in recent years, mainly due to their novel properties and their application in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). Structural information of Schiff base derivatives is useful in studying their coordination chemisty. As part of our research, we have synthesized the title compound (I) and report its crystal structure here.

The molecular structure is shown in Fig. 1. Each molecule is non-planar, with dihedral angles of 45.2 (2) and 56.6 (2)° between the pyridine ring and the benzene ring for the two molecules. Bond lengths and angles agree with those found for isonicotinohydrazide derivatives (Qian et al., 2006).

Intermolecular N—H···O hydrogen bonds link pairs of molecules.

Related literature top

For related literature, see: Kahwa et al. (1986); Qian et al. (2006); Santos et al. (2001).

Experimental top

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous methanol, whereafter H₂SO₄ (98%, 0.5 ml) was added and the mixture was stirred for several minutes at 351 K. A solution of cinnamaldehyde (1 mmol, 0.132 g) in methanol (8 ml) was then added dropwise and the mixture was stirred under reflux for 2 h. The product was isolated and recrystallized from dichloromethane, brown single crystals of (I) were obtained after 2 d.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP plot of (I) showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

N'-(3-Phenylallylidene)isonicotinohydrazide top

Crystal data top

C₁₅H₁₃N₃O	F(000) = 528
M_r = 251.28	D_x = 1.244 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 940 reflections
a = 12.608 (8) Å	θ = 2.5–20.5°
b = 11.023 (7) Å	µ = 0.08 mm⁻¹
c = 10.044 (7) Å	T = 291 K
β = 105.94 (3)°	Block, brown
V = 1342.2 (15) Å³	0.30 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3110 independent reflections
Radiation source: sealed tube	2784 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 27.7°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
T_min = 0.98, T_max = 0.98	k = −13→14
11645 measured reflections	l = −13→12

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.05P)² + 0.88P] where P = (F_o² + 2F_c²)/3
3110 reflections	(Δ/σ)_max < 0.001
349 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O	V = 1342.2 (15) Å³
M_r = 251.28	Z = 4
Monoclinic, Pc	Mo Kα radiation
a = 12.608 (8) Å	µ = 0.08 mm⁻¹
b = 11.023 (7) Å	T = 291 K
c = 10.044 (7) Å	0.30 × 0.26 × 0.24 mm
β = 105.94 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3110 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2784 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.98	R_int = 0.044
11645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	2 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.20 e Å⁻³
3110 reflections	Δρ_min = −0.29 e Å⁻³
349 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

	x	y	z	U_iso*/U_eq
C1	1.2011 (4)	0.4816 (5)	0.8674 (5)	0.0472 (10)
H1	1.2238	0.5562	0.8420	0.057*
C2	1.2551 (4)	0.4303 (4)	0.9917 (5)	0.0457 (10)
H2	1.3139	0.4716	1.0505	0.055*
C3	1.2239 (4)	0.3174 (4)	1.0323 (5)	0.0417 (9)
H3	1.2609	0.2838	1.1173	0.050*
C4	1.1362 (4)	0.2566 (4)	0.9422 (4)	0.0418 (10)
H4	1.1148	0.1809	0.9666	0.050*
C5	1.0805 (4)	0.3081 (5)	0.8167 (4)	0.0469 (11)
H5	1.0219	0.2672	0.7571	0.056*
C6	1.1126 (3)	0.4217 (4)	0.7798 (5)	0.0421 (9)
C7	1.0508 (3)	0.4875 (4)	0.6585 (5)	0.0426 (10)
H7	1.0694	0.5672	0.6446	0.051*
C8	0.9646 (4)	0.4321 (4)	0.5637 (5)	0.0436 (10)
H8	0.9451	0.3521	0.5747	0.052*
C9	0.9049 (4)	0.5050 (4)	0.4446 (4)	0.0435 (10)
H9	0.9175	0.5870	0.4333	0.052*
C10	0.6810 (4)	0.4686 (4)	0.1451 (4)	0.0391 (9)
C11	0.5998 (4)	0.5425 (4)	0.0516 (4)	0.0438 (10)
C12	0.5471 (3)	0.5017 (4)	−0.0823 (4)	0.0356 (8)
H12	0.5587	0.4233	−0.1093	0.043*
C13	0.4793 (4)	0.5778 (4)	−0.1716 (5)	0.0413 (9)
H13	0.4438	0.5497	−0.2599	0.050*
C14	0.5136 (4)	0.7372 (4)	−0.0082 (4)	0.0427 (9)
H14	0.5025	0.8165	0.0165	0.051*
C15	0.5845 (3)	0.6620 (4)	0.0872 (4)	0.0432 (10)
H15	0.6216	0.6914	0.1743	0.052*
C16	0.4052 (4)	0.0511 (4)	−0.2985 (4)	0.0424 (9)
H16	0.4482	−0.0181	−0.2728	0.051*
C17	0.3238 (3)	0.0544 (4)	−0.4232 (4)	0.0400 (9)
H17	0.3127	−0.0128	−0.4814	0.048*
C18	0.2588 (4)	0.1560 (4)	−0.4623 (5)	0.0455 (10)
H18	0.2039	0.1569	−0.5459	0.055*
C19	0.2761 (4)	0.2580 (4)	−0.3752 (4)	0.0417 (9)
H19	0.2328	0.3269	−0.4015	0.050*
C20	0.3577 (3)	0.2565 (4)	−0.2498 (4)	0.0356 (8)
H20	0.3689	0.3242	−0.1923	0.043*
C21	0.4226 (4)	0.1536 (4)	−0.2104 (4)	0.0462 (10)
C22	0.5026 (4)	0.1586 (4)	−0.0775 (5)	0.0462 (10)
H22	0.5019	0.2227	−0.0175	0.055*
C23	0.5807 (4)	0.0677 (4)	−0.0391 (4)	0.0433 (10)
H23	0.5931	0.0067	−0.0970	0.052*
C24	0.6411 (3)	0.0828 (4)	0.1081 (4)	0.0398 (9)
H24	0.6423	0.1533	0.1594	0.048*
C25	0.8300 (4)	−0.1108 (5)	0.3489 (5)	0.0502 (11)
C26	0.8954 (4)	−0.0909 (4)	0.4904 (5)	0.0441 (10)
C27	0.9750 (4)	−0.0014 (4)	0.5288 (5)	0.0405 (9)
H27	0.9822	0.0570	0.4650	0.049*
C28	1.0442 (4)	0.0012 (5)	0.6632 (5)	0.0505 (11)
H28	1.0965	0.0623	0.6904	0.061*
C29	0.9555 (3)	−0.1774 (4)	0.7183 (4)	0.0421 (9)
H29	0.9483	−0.2360	0.7819	0.051*
C30	0.8865 (3)	−0.1796 (3)	0.5848 (4)	0.0337 (8)
H30	0.8341	−0.2407	0.5582	0.040*
N1	0.8334 (3)	0.4414 (3)	0.3586 (4)	0.0397 (8)
N2	0.7663 (3)	0.5206 (4)	0.2548 (4)	0.0423 (9)
H2A	0.777 (4)	0.598 (5)	0.259 (5)	0.051*
N3	0.4603 (3)	0.6964 (3)	−0.1372 (3)	0.0392 (8)
N4	0.6918 (3)	−0.0162 (3)	0.1548 (4)	0.0424 (8)
N5	0.7800 (3)	−0.0023 (3)	0.2797 (3)	0.0368 (8)
H5A	0.833 (4)	0.042 (4)	0.259 (5)	0.044*
N6	1.0342 (3)	−0.0891 (4)	0.7569 (4)	0.0491 (9)
O1	0.6774 (2)	0.3578 (3)	0.1322 (3)	0.0434 (7)
O2	0.8172 (2)	−0.2090 (3)	0.2914 (3)	0.0440 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (2)	0.052 (3)	0.051 (3)	−0.006 (2)	0.019 (2)	0.004 (2)
C2	0.042 (2)	0.048 (2)	0.049 (3)	−0.0034 (19)	0.017 (2)	−0.011 (2)
C3	0.043 (2)	0.044 (2)	0.043 (2)	0.0020 (18)	0.0214 (19)	−0.0022 (18)
C4	0.048 (2)	0.042 (2)	0.042 (2)	−0.0146 (18)	0.0227 (19)	0.0100 (17)
C5	0.037 (2)	0.071 (3)	0.035 (2)	−0.014 (2)	0.0134 (17)	−0.010 (2)
C6	0.0332 (18)	0.050 (2)	0.046 (2)	0.0070 (18)	0.0149 (17)	−0.0088 (19)
C7	0.037 (2)	0.043 (2)	0.054 (3)	0.0071 (18)	0.0238 (19)	−0.014 (2)
C8	0.040 (2)	0.041 (2)	0.053 (3)	0.0142 (18)	0.0167 (19)	0.0057 (19)
C9	0.051 (2)	0.050 (2)	0.0264 (19)	0.003 (2)	0.0053 (17)	−0.0123 (18)
C10	0.044 (2)	0.036 (2)	0.040 (2)	−0.0233 (18)	0.0151 (17)	0.0063 (17)
C11	0.054 (3)	0.041 (2)	0.038 (2)	−0.006 (2)	0.0163 (19)	−0.0013 (18)
C12	0.0331 (19)	0.038 (2)	0.043 (2)	0.0074 (16)	0.0221 (16)	−0.0088 (16)
C13	0.042 (2)	0.046 (2)	0.040 (2)	−0.0041 (19)	0.0172 (18)	−0.0042 (18)
C14	0.048 (2)	0.042 (2)	0.037 (2)	−0.0053 (19)	0.0103 (18)	−0.0103 (18)
C15	0.041 (2)	0.056 (3)	0.032 (2)	−0.0076 (19)	0.0092 (17)	−0.0133 (18)
C16	0.051 (2)	0.045 (2)	0.031 (2)	−0.005 (2)	0.0121 (17)	0.0038 (17)
C17	0.036 (2)	0.046 (2)	0.036 (2)	−0.0121 (17)	0.0074 (17)	−0.0079 (17)
C18	0.047 (2)	0.047 (2)	0.043 (2)	−0.0120 (19)	0.0108 (19)	−0.013 (2)
C19	0.049 (2)	0.043 (2)	0.034 (2)	−0.0036 (19)	0.0128 (18)	−0.0051 (17)
C20	0.0386 (19)	0.036 (2)	0.037 (2)	−0.0144 (16)	0.0175 (16)	0.0037 (16)
C21	0.055 (3)	0.051 (3)	0.037 (2)	−0.004 (2)	0.0198 (19)	0.0099 (19)
C22	0.046 (2)	0.044 (2)	0.051 (3)	0.0147 (19)	0.018 (2)	−0.0061 (19)
C23	0.044 (2)	0.045 (2)	0.040 (2)	0.0018 (19)	0.0095 (18)	−0.0135 (18)
C24	0.0314 (18)	0.052 (2)	0.037 (2)	−0.0043 (17)	0.0113 (16)	−0.0110 (18)
C25	0.050 (2)	0.052 (3)	0.054 (3)	0.013 (2)	0.022 (2)	0.003 (2)
C26	0.047 (2)	0.045 (2)	0.049 (3)	0.003 (2)	0.028 (2)	0.005 (2)
C27	0.038 (2)	0.046 (2)	0.044 (2)	0.0001 (17)	0.0225 (18)	0.0012 (18)
C28	0.050 (2)	0.063 (3)	0.038 (2)	−0.011 (2)	0.0126 (19)	−0.009 (2)
C29	0.040 (2)	0.047 (2)	0.044 (2)	0.0067 (18)	0.0202 (18)	−0.0077 (18)
C30	0.0285 (16)	0.0339 (19)	0.044 (2)	0.0102 (14)	0.0190 (15)	−0.0027 (16)
N1	0.0374 (17)	0.0327 (17)	0.0451 (19)	−0.0052 (14)	0.0045 (14)	0.0001 (14)
N2	0.0305 (17)	0.045 (2)	0.0435 (19)	−0.0151 (15)	−0.0034 (14)	0.0138 (16)
N3	0.0488 (19)	0.0410 (19)	0.0321 (17)	0.0031 (16)	0.0182 (14)	0.0002 (15)
N4	0.055 (2)	0.0406 (19)	0.0303 (17)	−0.0081 (17)	0.0093 (16)	−0.0039 (15)
N5	0.0338 (17)	0.0399 (18)	0.0350 (18)	−0.0151 (14)	0.0064 (14)	−0.0011 (14)
N6	0.043 (2)	0.062 (2)	0.049 (2)	−0.0020 (18)	0.0230 (17)	−0.0041 (19)
O1	0.0396 (15)	0.0449 (17)	0.0474 (17)	−0.0096 (13)	0.0152 (13)	−0.0059 (13)
O2	0.0434 (15)	0.0455 (17)	0.0413 (16)	0.0001 (13)	0.0084 (12)	0.0034 (14)

Geometric parameters (Å, º) top

C1—C2	1.369 (7)	C16—H16	0.9300
C1—C6	1.385 (7)	C17—C18	1.379 (7)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.400 (6)	C18—C19	1.405 (6)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.394 (6)	C19—C20	1.391 (6)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.386 (6)	C20—C21	1.391 (6)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.397 (7)	C21—C22	1.437 (6)
C5—H5	0.9300	C22—C23	1.383 (6)
C6—C7	1.447 (7)	C22—H22	0.9300
C7—C8	1.375 (7)	C23—C24	1.475 (6)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.467 (6)	C24—N4	1.287 (6)
C8—H8	0.9300	C24—H24	0.9300
C9—N1	1.273 (5)	C25—O2	1.216 (6)
C9—H9	0.9300	C25—N5	1.439 (6)
C10—O1	1.228 (5)	C25—C26	1.451 (7)
C10—N2	1.432 (5)	C26—C27	1.385 (6)
C10—C11	1.437 (6)	C26—C30	1.388 (6)
C11—C15	1.393 (6)	C27—C28	1.391 (7)
C11—C12	1.400 (6)	C27—H27	0.9300
C12—C13	1.347 (6)	C28—N6	1.399 (7)
C12—H12	0.9300	C28—H28	0.9300
C13—N3	1.390 (6)	C29—N6	1.368 (6)
C13—H13	0.9300	C29—C30	1.384 (6)
C14—N3	1.362 (5)	C29—H29	0.9300
C14—C15	1.390 (7)	C30—H30	0.9300
C14—H14	0.9300	N1—N2	1.442 (5)
C15—H15	0.9300	N2—H2A	0.86 (5)
C16—C17	1.385 (6)	N4—N5	1.437 (5)
C16—C21	1.415 (7)	N5—H5A	0.90 (5)

C2—C1—C6	119.7 (5)	C16—C17—H17	119.6
C2—C1—H1	120.1	C17—C18—C19	119.6 (4)
C6—C1—H1	120.1	C17—C18—H18	120.2
C1—C2—C3	121.6 (4)	C19—C18—H18	120.2
C1—C2—H2	119.2	C20—C19—C18	120.3 (4)
C3—C2—H2	119.2	C20—C19—H19	119.9
C4—C3—C2	118.4 (4)	C18—C19—H19	119.9
C4—C3—H3	120.8	C21—C20—C19	119.9 (4)
C2—C3—H3	120.8	C21—C20—H20	120.1
C5—C4—C3	120.5 (4)	C19—C20—H20	120.1
C5—C4—H4	119.8	C20—C21—C16	119.7 (4)
C3—C4—H4	119.8	C20—C21—C22	116.2 (4)
C4—C5—C6	119.9 (4)	C16—C21—C22	124.1 (4)
C4—C5—H5	120.1	C23—C22—C21	119.7 (4)
C6—C5—H5	120.1	C23—C22—H22	120.1
C1—C6—C5	120.0 (4)	C21—C22—H22	120.1
C1—C6—C7	116.7 (5)	C22—C23—C24	109.2 (4)
C5—C6—C7	123.0 (4)	C22—C23—H23	125.4
C8—C7—C6	120.0 (4)	C24—C23—H23	125.4
C8—C7—H7	120.0	N4—C24—C23	109.7 (4)
C6—C7—H7	120.0	N4—C24—H24	125.1
C7—C8—C9	116.9 (4)	C23—C24—H24	125.1
C7—C8—H8	121.5	O2—C25—N5	121.8 (5)
C9—C8—H8	121.5	O2—C25—C26	124.4 (4)
N1—C9—C8	111.1 (4)	N5—C25—C26	113.8 (4)
N1—C9—H9	124.4	C27—C26—C30	120.0 (4)
C8—C9—H9	124.4	C27—C26—C25	123.7 (4)
O1—C10—N2	118.5 (4)	C30—C26—C25	115.6 (4)
O1—C10—C11	119.7 (4)	C26—C27—C28	119.9 (4)
N2—C10—C11	121.7 (4)	C26—C27—H27	120.1
C15—C11—C12	119.1 (4)	C28—C27—H27	120.1
C15—C11—C10	119.5 (4)	C27—C28—N6	119.3 (4)
C12—C11—C10	120.7 (4)	C27—C28—H28	120.3
C13—C12—C11	119.1 (4)	N6—C28—H28	120.3
C13—C12—H12	120.4	N6—C29—C30	120.1 (4)
C11—C12—H12	120.4	N6—C29—H29	120.0
C12—C13—N3	122.8 (4)	C30—C29—H29	120.0
C12—C13—H13	118.6	C29—C30—C26	120.2 (4)
N3—C13—H13	118.6	C29—C30—H30	119.9
N3—C14—C15	121.0 (4)	C26—C30—H30	119.9
N3—C14—H14	119.5	C9—N1—N2	108.8 (4)
C15—C14—H14	119.5	C10—N2—N1	118.8 (3)
C14—C15—C11	119.7 (4)	C10—N2—H2A	121 (3)
C14—C15—H15	120.1	N1—N2—H2A	121 (3)
C11—C15—H15	120.1	C14—N3—C13	118.2 (4)
C17—C16—C21	119.6 (4)	C24—N4—N5	114.5 (3)
C17—C16—H16	120.2	N4—N5—C25	117.7 (4)
C21—C16—H16	120.2	N4—N5—H5A	108 (3)
C18—C17—C16	120.9 (4)	C25—N5—H5A	108 (3)
C18—C17—H17	119.6	C29—N6—C28	120.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86 (5)	2.19 (5)	3.050 (6)	174 (3)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O
M_r	251.28
Crystal system, space group	Monoclinic, Pc
Temperature (K)	291
a, b, c (Å)	12.608 (8), 11.023 (7), 10.044 (7)
β (°)	105.94 (3)
V (Å³)	1342.2 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.98, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	11645, 3110, 2784
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.134, 1.01
No. of reflections	3110
No. of parameters	349
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86 (5)	2.19 (5)	3.050 (6)	174 (3)

Symmetry code: (i) x, y+1, z.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Qian, H.-Y., Yin, Z.-G., Jia, J., Liu, S.-M. & Feng, L.-Q. (2006). Acta Cryst. E62, o3623–o3624. CSD CrossRef IUCr Journals Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1789

doi:10.1107/S1600536808026287

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