2-Cyano-N'-[(E)-1-(2-oxo-2H-chromen-3-yl)ethyl-idene]acetohydrazide.

In the title compound, C(14)H(11)N(3)O(3), the chromene ring is almost planar, with a maximum deviation of 0.065 (2) Å from the mean plane for one of the C atoms. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked by C-H⋯N and C-H⋯O inter-actions into a three-dimensional network. An aromatic π-π stacking inter-action, with a centroid-centroid distance of 3.562 (10) Å, is also observed.

Related literature

For related structures and background to coumarin, see: Yusufzai, Osman, Sulaiman et al. (2012 ▶); Yusufzai, Osman, Abdul Rahim et al. (2012 ▶).

Experimental

Crystal data

C14H11N3O3

M = 269.26

Monoclinic,

a = 10.4755 (2) Å

b = 15.8283 (3) Å

c = 8.2650 (2) Å

β = 106.982 (2)°

V = 1310.66 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.20 × 0.18 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.980, T max = 0.988

13242 measured reflections

3020 independent reflections

1987 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.120

S = 1.03

3020 reflections

225 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019915/hb6757sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019915/hb6757Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019915/hb6757Isup3.cml

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

C14H11N3O3	F(000) = 560
Mr = 269.26	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1883 reflections
a = 10.4755 (2) Å	θ = 2.9–32.3°
b = 15.8283 (3) Å	µ = 0.10 mm−1
c = 8.2650 (2) Å	T = 100 K
β = 106.982 (2)°	Block, yellow
V = 1310.66 (5) Å3	0.20 × 0.18 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3020 independent reflections
Radiation source: fine-focus sealed tube	1987 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→11
Tmin = 0.980, Tmax = 0.988	k = −20→20
13242 measured reflections	l = −10→10

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.221P] where P = (Fo2 + 2Fc2)/3
3020 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.63816 (12)	0.09170 (8)	0.75003 (16)	0.0247 (3)
O2	0.51923 (13)	0.17039 (9)	0.87086 (18)	0.0315 (4)
O3	0.00031 (13)	−0.10885 (9)	1.00205 (17)	0.0299 (4)
N1	0.26272 (15)	−0.03027 (11)	0.86808 (19)	0.0240 (4)
N2	0.14627 (15)	−0.02929 (11)	0.9143 (2)	0.0248 (4)
N3	0.05268 (18)	−0.31915 (12)	0.9689 (2)	0.0381 (5)
C1	0.52801 (19)	0.10271 (13)	0.8072 (2)	0.0244 (4)
C2	0.67126 (19)	0.01490 (12)	0.6931 (2)	0.0225 (4)
C3	0.7888 (2)	0.01131 (14)	0.6498 (2)	0.0266 (5)
C4	0.8249 (2)	−0.06527 (14)	0.5953 (2)	0.0290 (5)
C5	0.7453 (2)	−0.13655 (14)	0.5845 (2)	0.0287 (5)
C6	0.6272 (2)	−0.13152 (14)	0.6261 (2)	0.0271 (5)
C7	0.58787 (19)	−0.05499 (12)	0.6825 (2)	0.0223 (4)
C8	0.46742 (19)	−0.04304 (13)	0.7273 (2)	0.0228 (4)
C9	0.43492 (18)	0.03136 (12)	0.7863 (2)	0.0225 (4)
C10	0.31072 (18)	0.04074 (13)	0.8374 (2)	0.0220 (4)
C11	0.2471 (2)	0.12496 (14)	0.8465 (3)	0.0289 (5)
C12	0.09542 (19)	−0.10427 (13)	0.9446 (2)	0.0241 (4)
C13	0.1621 (2)	−0.18236 (13)	0.9000 (3)	0.0261 (5)
C14	0.09896 (19)	−0.25873 (14)	0.9385 (2)	0.0267 (5)
H3A	0.8460 (19)	0.0623 (14)	0.658 (2)	0.029 (6)*
H4A	0.906 (2)	−0.0682 (13)	0.564 (2)	0.031 (6)*
H6A	0.571 (2)	−0.1803 (14)	0.617 (2)	0.033 (6)*
H5A	0.7711 (19)	−0.1885 (14)	0.543 (2)	0.030 (6)*
H8A	0.4042 (19)	−0.0902 (13)	0.714 (2)	0.026 (5)*
H11A	0.153 (2)	0.1204 (14)	0.794 (3)	0.035 (6)*
H11B	0.284 (2)	0.1687 (15)	0.787 (3)	0.045 (7)*
H11C	0.257 (3)	0.1423 (17)	0.966 (4)	0.075 (9)*
H13A	0.255 (2)	−0.1847 (14)	0.962 (3)	0.040 (6)*
H13B	0.155 (2)	−0.1803 (14)	0.777 (3)	0.043 (6)*
H1N2	0.102 (2)	0.0198 (16)	0.941 (3)	0.049 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0218 (7)	0.0214 (8)	0.0357 (7)	0.0000 (6)	0.0159 (6)	−0.0019 (6)
O2	0.0266 (8)	0.0227 (8)	0.0483 (8)	0.0012 (6)	0.0160 (7)	−0.0072 (7)
O3	0.0265 (8)	0.0287 (9)	0.0423 (8)	−0.0002 (6)	0.0224 (6)	0.0001 (6)
N1	0.0211 (8)	0.0269 (10)	0.0284 (8)	−0.0005 (7)	0.0137 (7)	0.0006 (7)
N2	0.0215 (9)	0.0242 (10)	0.0340 (9)	0.0006 (8)	0.0161 (7)	0.0002 (7)
N3	0.0403 (11)	0.0299 (12)	0.0514 (11)	−0.0052 (9)	0.0246 (9)	−0.0030 (9)
C1	0.0232 (10)	0.0214 (11)	0.0302 (10)	0.0036 (8)	0.0104 (8)	0.0023 (8)
C2	0.0248 (10)	0.0186 (11)	0.0258 (9)	0.0048 (8)	0.0097 (8)	0.0000 (8)
C3	0.0241 (10)	0.0275 (13)	0.0313 (10)	−0.0003 (9)	0.0131 (8)	0.0005 (9)
C4	0.0231 (11)	0.0334 (13)	0.0348 (11)	0.0039 (9)	0.0153 (9)	−0.0005 (9)
C5	0.0317 (12)	0.0251 (12)	0.0331 (11)	0.0064 (10)	0.0152 (9)	−0.0009 (9)
C6	0.0319 (11)	0.0201 (12)	0.0329 (10)	0.0008 (9)	0.0154 (9)	0.0008 (9)
C7	0.0238 (10)	0.0199 (11)	0.0259 (9)	0.0023 (8)	0.0113 (8)	0.0015 (8)
C8	0.0252 (10)	0.0188 (11)	0.0278 (10)	−0.0016 (9)	0.0130 (8)	0.0019 (8)
C9	0.0220 (10)	0.0211 (11)	0.0272 (9)	0.0002 (8)	0.0116 (8)	0.0017 (8)
C10	0.0207 (10)	0.0241 (12)	0.0242 (9)	0.0009 (8)	0.0113 (8)	−0.0002 (8)
C11	0.0279 (12)	0.0255 (12)	0.0398 (12)	0.0032 (9)	0.0200 (10)	0.0034 (9)
C12	0.0226 (10)	0.0251 (12)	0.0277 (9)	0.0006 (9)	0.0118 (8)	−0.0004 (8)
C13	0.0252 (11)	0.0229 (12)	0.0357 (11)	−0.0032 (9)	0.0175 (9)	−0.0032 (9)
C14	0.0239 (10)	0.0265 (12)	0.0331 (10)	−0.0024 (9)	0.0137 (8)	−0.0049 (9)

O1—C1	1.379 (2)	C5—C6	1.380 (3)
O1—C2	1.384 (2)	C5—H5A	0.96 (2)
O2—C1	1.209 (2)	C6—C7	1.402 (3)
O3—C12	1.225 (2)	C6—H6A	0.96 (2)
N1—C10	1.287 (2)	C7—C8	1.428 (3)
N1—N2	1.381 (2)	C8—C9	1.356 (3)
N2—C12	1.354 (2)	C8—H8A	0.98 (2)
N2—H1N2	0.96 (2)	C9—C10	1.488 (3)
N3—C14	1.133 (3)	C10—C11	1.502 (3)
C1—C9	1.469 (3)	C11—H11A	0.95 (2)
C2—C3	1.380 (3)	C11—H11B	0.99 (2)
C2—C7	1.396 (3)	C11—H11C	1.00 (3)
C3—C4	1.384 (3)	C12—C13	1.517 (3)
C3—H3A	1.00 (2)	C13—C14	1.457 (3)
C4—C5	1.390 (3)	C13—H13A	0.96 (2)
C4—H4A	0.96 (2)	C13—H13B	1.00 (2)
C1—O1—C2	123.02 (15)	C9—C8—C7	122.84 (19)
C10—N1—N2	118.20 (17)	C9—C8—H8A	117.9 (12)
C12—N2—N1	117.93 (17)	C7—C8—H8A	119.3 (12)
C12—N2—H1N2	114.9 (14)	C8—C9—C1	118.83 (18)
N1—N2—H1N2	126.7 (14)	C8—C9—C10	121.40 (18)
O2—C1—O1	116.01 (17)	C1—C9—C10	119.72 (17)
O2—C1—C9	126.87 (18)	N1—C10—C9	113.17 (17)
O1—C1—C9	117.12 (17)	N1—C10—C11	124.11 (18)
C3—C2—O1	117.10 (18)	C9—C10—C11	122.70 (18)
C3—C2—C7	122.69 (19)	C10—C11—H11A	108.8 (13)
O1—C2—C7	120.21 (17)	C10—C11—H11B	110.5 (13)
C2—C3—C4	118.0 (2)	H11A—C11—H11B	109.1 (18)
C2—C3—H3A	120.9 (12)	C10—C11—H11C	112.0 (16)
C4—C3—H3A	121.1 (12)	H11A—C11—H11C	105 (2)
C3—C4—C5	121.1 (2)	H11B—C11—H11C	111 (2)
C3—C4—H4A	118.5 (13)	O3—C12—N2	122.15 (18)
C5—C4—H4A	120.4 (13)	O3—C12—C13	122.03 (18)
C6—C5—C4	120.1 (2)	N2—C12—C13	115.81 (17)
C6—C5—H5A	120.3 (12)	C14—C13—C12	110.63 (16)
C4—C5—H5A	119.6 (12)	C14—C13—H13A	107.8 (13)
C5—C6—C7	120.3 (2)	C12—C13—H13A	111.6 (13)
C5—C6—H6A	120.7 (12)	C14—C13—H13B	110.2 (13)
C7—C6—H6A	119.0 (12)	C12—C13—H13B	108.4 (13)
C2—C7—C6	117.80 (18)	H13A—C13—H13B	108.2 (18)
C2—C7—C8	117.57 (18)	N3—C14—C13	178.3 (2)
C6—C7—C8	124.62 (19)
C10—N1—N2—C12	179.26 (16)	C7—C8—C9—C1	−0.7 (3)
C2—O1—C1—O2	171.92 (16)	C7—C8—C9—C10	−177.89 (17)
C2—O1—C1—C9	−7.4 (2)	O2—C1—C9—C8	−173.41 (19)
C1—O1—C2—C3	−175.90 (16)	O1—C1—C9—C8	5.9 (3)
C1—O1—C2—C7	3.7 (2)	O2—C1—C9—C10	3.8 (3)
O1—C2—C3—C4	178.95 (16)	O1—C1—C9—C10	−176.90 (15)
C7—C2—C3—C4	−0.6 (3)	N2—N1—C10—C9	−179.11 (15)
C2—C3—C4—C5	−0.1 (3)	N2—N1—C10—C11	−0.8 (3)
C3—C4—C5—C6	1.0 (3)	C8—C9—C10—N1	19.6 (2)
C4—C5—C6—C7	−1.2 (3)	C1—C9—C10—N1	−157.52 (16)
C3—C2—C7—C6	0.4 (3)	C8—C9—C10—C11	−158.73 (18)
O1—C2—C7—C6	−179.18 (16)	C1—C9—C10—C11	24.1 (3)
C3—C2—C7—C8	−178.66 (17)	N1—N2—C12—O3	172.68 (16)
O1—C2—C7—C8	1.8 (3)	N1—N2—C12—C13	−8.4 (2)
C5—C6—C7—C2	0.5 (3)	O3—C12—C13—C14	−1.2 (3)
C5—C6—C7—C8	179.50 (18)	N2—C12—C13—C14	179.88 (16)
C2—C7—C8—C9	−3.2 (3)	C12—C13—C14—N3	−154 (7)
C6—C7—C8—C9	177.89 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3i	0.96 (2)	1.91 (2)	2.870 (2)	174 (2)
C3—H3A···N3ii	1.00 (2)	2.53 (2)	3.446 (3)	152.9 (12)
C4—H4A···N3iii	0.96 (2)	2.62 (2)	3.404 (3)	139.2 (16)
C6—H6A···O2iv	0.96 (2)	2.56 (2)	3.494 (3)	164.7 (17)
C13—H13A···O2v	0.96 (2)	2.38 (2)	3.328 (3)	171.7 (18)
C13—H13B···N3vi	1.00 (2)	2.46 (2)	3.409 (3)	159.3 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3i	0.96 (2)	1.91 (2)	2.870 (2)	174 (2)
C3—H3A⋯N3ii	1.00 (2)	2.53 (2)	3.446 (3)	152.9 (12)
C4—H4A⋯N3iii	0.96 (2)	2.62 (2)	3.404 (3)	139.2 (16)
C6—H6A⋯O2iv	0.96 (2)	2.56 (2)	3.494 (3)	164.7 (17)
C13—H13A⋯O2v	0.96 (2)	2.38 (2)	3.328 (3)	171.7 (18)
C13—H13B⋯N3vi	1.00 (2)	2.46 (2)	3.409 (3)	159.3 (18)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .