N'-(3-Phenyl-allyl-idene)isonicotino-hydrazide.

The asymmetric unit of the title compound, C(15)H(13)N(3)O, contains two similar mol-ecules. Each mol-ecule 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 inter-molecular 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 = 251.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.134

S = 1.01

3110 reflections

349 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H13N3O	F000 = 528
Mr = 251.28	Dx = 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 = 2.5–20.5º
b = 11.023 (7) Å	µ = 0.08 mm−1
c = 10.044 (7) Å	T = 291 (2) K
β = 105.94 (3)º	Block, brown
V = 1342.2 (15) Å3	0.30 × 0.26 × 0.24 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3110 independent reflections
Radiation source: sealed tube	2784 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
T = 291(2) K	θmax = 27.7º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.98, Tmax = 0.98	k = −13→14
11645 measured reflections	l = −13→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.05P)2 + 0.88P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3110 reflections	Δρmax = 0.20 e Å−3
349 parameters	Δρmin = −0.29 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) .