4-{(E)-[2-(Pyridin-3-ylcarbon-yl)hydrazinyl-idene]meth-yl}phenyl acetate.

The title compound, C15H13N3O3, exists in the E conformation with respect to the azo-methane C=N double bond. The pyridyl and phenyl rings form dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the central C(=O)N2C unit. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds connect the mol-ecules into chains along the b axis. Another C-H⋯O inter-action connects mol-ecules along the c-axis direction, forming layers.

Related literature

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004 ▶); Rakha et al. (1996 ▶); Takahama (1996 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶). For related structures, see: Reshma et al. (2012 ▶).

Experimental

Crystal data

C15H13N3O3

M = 283.28

Monoclinic,

a = 16.347 (4) Å

b = 5.0859 (10) Å

c = 18.408 (5) Å

β = 115.311 (9)°

V = 1383.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.953, T max = 0.976

9585 measured reflections

3325 independent reflections

2288 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.140

S = 1.04

3325 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536813025075/fj2641sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025075/fj2641Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025075/fj2641Isup3.cml

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

C15H13N3O3	F(000) = 592
Mr = 283.28	Dx = 1.360 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2983 reflections
a = 16.347 (4) Å	θ = 2.8–26.9°
b = 5.0859 (10) Å	µ = 0.10 mm−1
c = 18.408 (5) Å	T = 296 K
β = 115.311 (9)°	Block, colorless
V = 1383.6 (6) Å3	0.50 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3325 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm-1	θmax = 28.0°, θmin = 2.2°
ω and φ scan	h = −21→19
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −6→6
Tmin = 0.953, Tmax = 0.976	l = −23→24
9585 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3098P] where P = (Fo2 + 2Fc2)/3
3325 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

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
O1	0.62319 (9)	−0.2235 (2)	−0.00860 (7)	0.0554 (4)
O2	0.64307 (10)	0.4099 (3)	0.44141 (7)	0.0639 (4)
N1	0.72016 (12)	0.3431 (3)	−0.15907 (10)	0.0597 (4)
N2	0.62677 (10)	0.2123 (3)	0.01908 (8)	0.0427 (3)
N3	0.62691 (10)	0.1739 (3)	0.09359 (8)	0.0420 (3)
C1	0.70076 (13)	0.2839 (3)	−0.09748 (10)	0.0477 (4)
H1	0.7253	0.3894	−0.0519	0.057*
C2	0.68290 (15)	0.1905 (4)	−0.22385 (11)	0.0603 (5)
H2	0.6949	0.2292	−0.2677	0.072*
C3	0.62814 (14)	−0.0194 (4)	−0.22982 (11)	0.0596 (5)
H3	0.6035	−0.1191	−0.2766	0.071*
C4	0.61008 (12)	−0.0806 (4)	−0.16510 (10)	0.0493 (4)
H4	0.5741	−0.2244	−0.1671	0.059*
C5	0.64659 (11)	0.0761 (3)	−0.09706 (9)	0.0365 (4)
C6	0.63100 (11)	0.0061 (3)	−0.02519 (10)	0.0380 (4)
C7	0.60960 (11)	0.3795 (3)	0.12422 (10)	0.0403 (4)
H7	0.5928	0.5334	0.0942	0.048*
C8	0.61583 (10)	0.3768 (3)	0.20592 (9)	0.0373 (4)
C9	0.66527 (12)	0.1856 (3)	0.26163 (10)	0.0457 (4)
H9	0.6934	0.0516	0.2464	0.055*
C10	0.67294 (12)	0.1932 (4)	0.33914 (10)	0.0510 (4)
H10	0.7064	0.0660	0.3762	0.061*
C11	0.63065 (12)	0.3906 (4)	0.36095 (10)	0.0477 (4)
C12	0.58098 (13)	0.5817 (4)	0.30759 (12)	0.0537 (5)
H12	0.5522	0.7130	0.3232	0.064*
C13	0.57459 (13)	0.5752 (3)	0.23019 (11)	0.0485 (4)
H13	0.5422	0.7056	0.1939	0.058*
C14	0.59039 (13)	0.2668 (4)	0.46456 (11)	0.0568 (5)
C15	0.61036 (14)	0.3114 (5)	0.55032 (11)	0.0647 (6)
H15A	0.6115	0.4968	0.5605	0.097*
H15B	0.6681	0.2362	0.5840	0.097*
H15C	0.5643	0.2299	0.5619	0.097*
H2'	0.6234 (12)	0.369 (2)	−0.0002 (10)	0.048 (5)*
O3	0.53569 (15)	0.1229 (5)	0.41928 (11)	0.1332 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0910 (10)	0.0271 (6)	0.0590 (8)	−0.0011 (6)	0.0423 (7)	0.0038 (5)
O2	0.0756 (9)	0.0812 (10)	0.0411 (7)	−0.0283 (8)	0.0308 (7)	−0.0160 (7)
N1	0.0870 (12)	0.0523 (9)	0.0551 (9)	−0.0080 (8)	0.0450 (9)	0.0004 (8)
N2	0.0680 (9)	0.0283 (7)	0.0422 (8)	0.0018 (6)	0.0335 (7)	0.0051 (6)
N3	0.0589 (9)	0.0354 (7)	0.0401 (7)	−0.0009 (6)	0.0292 (6)	0.0034 (6)
C1	0.0674 (11)	0.0391 (9)	0.0435 (9)	−0.0065 (8)	0.0304 (9)	−0.0046 (7)
C2	0.0835 (14)	0.0644 (12)	0.0435 (10)	0.0063 (11)	0.0373 (10)	0.0064 (9)
C3	0.0724 (13)	0.0663 (13)	0.0356 (9)	0.0018 (10)	0.0189 (9)	−0.0102 (9)
C4	0.0540 (10)	0.0445 (9)	0.0458 (10)	−0.0027 (8)	0.0180 (8)	−0.0067 (8)
C5	0.0452 (8)	0.0296 (7)	0.0353 (8)	0.0060 (6)	0.0178 (7)	0.0034 (6)
C6	0.0484 (9)	0.0280 (8)	0.0399 (8)	0.0014 (6)	0.0209 (7)	0.0037 (6)
C7	0.0502 (9)	0.0336 (8)	0.0426 (9)	−0.0010 (7)	0.0252 (7)	0.0053 (7)
C8	0.0429 (8)	0.0349 (8)	0.0403 (8)	−0.0055 (6)	0.0237 (7)	−0.0007 (6)
C9	0.0494 (9)	0.0449 (9)	0.0471 (10)	0.0039 (7)	0.0248 (8)	0.0017 (8)
C10	0.0560 (10)	0.0550 (11)	0.0404 (9)	0.0027 (8)	0.0190 (8)	0.0061 (8)
C11	0.0543 (10)	0.0549 (11)	0.0384 (9)	−0.0167 (8)	0.0240 (8)	−0.0100 (8)
C12	0.0691 (12)	0.0469 (10)	0.0570 (11)	−0.0012 (9)	0.0384 (10)	−0.0091 (9)
C13	0.0602 (11)	0.0388 (9)	0.0513 (10)	0.0034 (8)	0.0285 (8)	0.0018 (8)
C14	0.0563 (11)	0.0758 (13)	0.0406 (9)	−0.0116 (10)	0.0230 (8)	−0.0064 (9)
C15	0.0679 (13)	0.0904 (16)	0.0411 (10)	−0.0038 (11)	0.0282 (9)	−0.0026 (10)
O3	0.1493 (18)	0.203 (2)	0.0656 (11)	−0.1225 (18)	0.0636 (12)	−0.0513 (13)

O1—C6	1.2277 (18)	C7—C8	1.463 (2)
O2—C14	1.329 (2)	C7—H7	0.9300
O2—C11	1.410 (2)	C8—C13	1.389 (2)
N1—C2	1.332 (3)	C8—C9	1.394 (2)
N1—C1	1.336 (2)	C9—C10	1.378 (2)
N2—C6	1.348 (2)	C9—H9	0.9300
N2—N3	1.3844 (19)	C10—C11	1.373 (3)
N2—H2'	0.866 (9)	C10—H10	0.9300
N3—C7	1.276 (2)	C11—C12	1.374 (3)
C1—C5	1.381 (2)	C12—C13	1.384 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.367 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—O3	1.180 (2)
C3—C4	1.380 (3)	C14—C15	1.486 (3)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.386 (2)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.493 (2)
C14—O2—C11	118.47 (14)	C13—C8—C9	118.60 (16)
C2—N1—C1	116.41 (17)	C13—C8—C7	119.60 (15)
C6—N2—N3	120.70 (13)	C9—C8—C7	121.75 (15)
C6—N2—H2'	118.8 (12)	C10—C9—C8	120.64 (16)
N3—N2—H2'	120.5 (12)	C10—C9—H9	119.7
C7—N3—N2	114.55 (13)	C8—C9—H9	119.7
N1—C1—C5	124.26 (16)	C11—C10—C9	119.27 (17)
N1—C1—H1	117.9	C11—C10—H10	120.4
C5—C1—H1	117.9	C9—C10—H10	120.4
N1—C2—C3	124.06 (18)	C10—C11—C12	121.74 (16)
N1—C2—H2	118.0	C10—C11—O2	119.60 (17)
C3—C2—H2	118.0	C12—C11—O2	118.53 (17)
C2—C3—C4	118.76 (17)	C11—C12—C13	118.72 (17)
C2—C3—H3	120.6	C11—C12—H12	120.6
C4—C3—H3	120.6	C13—C12—H12	120.6
C3—C4—C5	118.82 (18)	C12—C13—C8	121.02 (17)
C3—C4—H4	120.6	C12—C13—H13	119.5
C5—C4—H4	120.6	C8—C13—H13	119.5
C1—C5—C4	117.67 (16)	O3—C14—O2	120.82 (18)
C1—C5—C6	122.69 (14)	O3—C14—C15	126.92 (19)
C4—C5—C6	119.53 (15)	O2—C14—C15	112.26 (17)
O1—C6—N2	123.50 (15)	C14—C15—H15A	109.5
O1—C6—C5	121.50 (14)	C14—C15—H15B	109.5
N2—C6—C5	115.00 (13)	H15A—C15—H15B	109.5
N3—C7—C8	121.05 (14)	C14—C15—H15C	109.5
N3—C7—H7	119.5	H15A—C15—H15C	109.5
C8—C7—H7	119.5	H15B—C15—H15C	109.5
C6—N2—N3—C7	−170.37 (15)	N3—C7—C8—C13	−163.02 (16)
C2—N1—C1—C5	0.9 (3)	N3—C7—C8—C9	19.6 (2)
C1—N1—C2—C3	−0.7 (3)	C13—C8—C9—C10	0.1 (2)
N1—C2—C3—C4	−0.4 (3)	C7—C8—C9—C10	177.51 (15)
C2—C3—C4—C5	1.3 (3)	C8—C9—C10—C11	0.5 (3)
N1—C1—C5—C4	0.0 (3)	C9—C10—C11—C12	−0.2 (3)
N1—C1—C5—C6	176.14 (16)	C9—C10—C11—O2	−175.82 (15)
C3—C4—C5—C1	−1.1 (2)	C14—O2—C11—C10	−85.1 (2)
C3—C4—C5—C6	−177.41 (16)	C14—O2—C11—C12	99.2 (2)
N3—N2—C6—O1	9.9 (3)	C10—C11—C12—C13	−0.7 (3)
N3—N2—C6—C5	−169.77 (13)	O2—C11—C12—C13	174.95 (16)
C1—C5—C6—O1	−144.25 (18)	C11—C12—C13—C8	1.3 (3)
C4—C5—C6—O1	31.8 (2)	C9—C8—C13—C12	−1.0 (3)
C1—C5—C6—N2	35.5 (2)	C7—C8—C13—C12	−178.50 (16)
C4—C5—C6—N2	−148.44 (16)	C11—O2—C14—O3	1.5 (3)
N2—N3—C7—C8	−174.03 (14)	C11—O2—C14—C15	−179.02 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O1i	0.87 (1)	2.08 (1)	2.9107 (18)	162 (2)
C7—H7···O1i	0.93	2.48	3.251 (2)	140
C15—H15C···O3ii	0.96	2.55	3.469 (4)	161
C4—H4···Cg1iii	0.93	3.13	3.821 (2)	133
C13—H13···Cg2iii	0.93	3.28	3.860 (3)	122
C15—H15A···Cg2iv	0.96	3.39	3.734 (3)	104
C15—H15B···Cg2iv	0.96	3.20	3.734 (3)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O1i	0.87 (1)	2.08 (1)	2.9107 (18)	162 (2)
C7—H7⋯O1i	0.93	2.48	3.251 (2)	140
C15—H15C⋯O3ii	0.96	2.55	3.469 (4)	161

Symmetry codes: (i) ; (ii) .