6-Amino-4-(4-chloro-phen-yl)-2-oxo-1,2-dihydro-pyridine-3,5-dicarbonitrile ethanol solvate.

The title compound, C(13)H(7)ClN(4)O·C(2)H(6)O, was synthesized by the reaction of 4-chloro-benzaldehyde, malononitrile and 10% sodium hydroxide solution in an aqueous medium. In the crystal structure, the crystal packing is stabilized by inter-molecular N-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Hasvold et al. (2003 ▶); Kappe (2004 ▶); Li et al. (2000 ▶); Mederski et al. (1999 ▶); Parlow et al. (2003 ▶); Varma (1999 ▶).

Experimental

Crystal data

C13H7ClN4O·C2H6O

M = 316.74

Triclinic,

a = 6.7787 (10) Å

b = 10.4318 (14) Å

c = 11.2857 (17) Å

α = 88.634 (2)°

β = 84.643 (1)°

γ = 81.700 (1)°

V = 786.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 298 (2) K

0.14 × 0.09 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.992

4165 measured reflections

2727 independent reflections

1162 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.140

S = 1.01

2727 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022551/bq2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022551/bq2082Isup2.hkl

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

C13H7ClN4O·C2H6O	Z = 2
Mr = 316.74	F000 = 328
Triclinic, P1	Dx = 1.338 Mg m−3
a = 6.7787 (10) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.4318 (14) Å	Cell parameters from 566 reflections
c = 11.2857 (17) Å	θ = 2.7–20.3º
α = 88.634 (2)º	µ = 0.26 mm−1
β = 84.6430 (10)º	T = 298 (2) K
γ = 81.7000 (10)º	Block, colorless
V = 786.2 (2) Å3	0.14 × 0.09 × 0.03 mm

Bruker SMART CCD area-detector diffractometer	2727 independent reflections
Radiation source: fine-focus sealed tube	1162 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.965, Tmax = 0.992	k = −7→12
4165 measured reflections	l = −13→11

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.0621P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2727 reflections	Δρmax = 0.31 e Å−3
199 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.3974 (2)	0.82840 (13)	−0.02206 (12)	0.0905 (6)
N1	0.5949 (5)	0.1640 (3)	0.4620 (3)	0.0420 (9)
H1	0.6264	0.0964	0.5051	0.050*
N2	0.8641 (5)	0.2447 (3)	0.5286 (3)	0.0520 (10)
H2A	0.8877	0.1748	0.5700	0.062*
H2B	0.9398	0.3040	0.5304	0.062*
N3	0.8433 (5)	0.5684 (4)	0.4171 (3)	0.0565 (11)
N4	0.0902 (6)	0.2779 (4)	0.1960 (3)	0.0705 (13)
O1	0.3337 (4)	0.0727 (3)	0.4075 (2)	0.0544 (9)
O2	−0.0003 (5)	0.0195 (3)	0.6598 (3)	0.0923 (13)
H2	−0.0927	−0.0237	0.6639	0.138*
C1	0.7115 (6)	0.2611 (4)	0.4621 (3)	0.0389 (11)
C2	0.6615 (5)	0.3715 (4)	0.3915 (3)	0.0353 (10)
C3	0.5067 (6)	0.3773 (4)	0.3158 (3)	0.0376 (10)
C4	0.3897 (6)	0.2774 (4)	0.3224 (3)	0.0389 (11)
C5	0.4310 (6)	0.1666 (4)	0.3979 (3)	0.0405 (11)
C6	0.7651 (6)	0.4800 (4)	0.4034 (3)	0.0422 (11)
C7	0.2249 (6)	0.2769 (4)	0.2514 (4)	0.0473 (12)
C8	0.4755 (6)	0.4877 (4)	0.2317 (3)	0.0389 (10)
C9	0.2890 (6)	0.5612 (4)	0.2250 (4)	0.0526 (12)
H9	0.1789	0.5406	0.2733	0.063*
C10	0.2668 (7)	0.6653 (5)	0.1464 (4)	0.0615 (14)
H10	0.1416	0.7145	0.1427	0.074*
C11	0.4283 (8)	0.6966 (4)	0.0736 (4)	0.0576 (13)
C12	0.6122 (7)	0.6221 (4)	0.0768 (4)	0.0494 (12)
H12	0.7202	0.6412	0.0259	0.059*
C13	0.6369 (6)	0.5191 (4)	0.1552 (3)	0.0425 (11)
H13	0.7622	0.4697	0.1574	0.051*
C14	0.0839 (8)	0.0126 (5)	0.7684 (4)	0.0776 (16)
H14A	0.1464	−0.0753	0.7828	0.093*
H14B	−0.0200	0.0359	0.8324	0.093*
C15	0.2369 (8)	0.1030 (5)	0.7664 (5)	0.0884 (18)
H15A	0.2941	0.0980	0.8413	0.133*
H15B	0.1743	0.1900	0.7528	0.133*
H15C	0.3404	0.0788	0.7037	0.133*

	U11	U22	U33	U12	U13	U23
Cl1	0.1212 (13)	0.0645 (10)	0.0815 (10)	−0.0005 (8)	−0.0159 (8)	0.0352 (8)
N1	0.050 (2)	0.032 (2)	0.049 (2)	−0.0153 (18)	−0.0145 (17)	0.0133 (18)
N2	0.058 (2)	0.041 (2)	0.065 (2)	−0.0234 (19)	−0.025 (2)	0.015 (2)
N3	0.064 (3)	0.056 (3)	0.057 (2)	−0.028 (2)	−0.016 (2)	0.010 (2)
N4	0.063 (3)	0.068 (3)	0.088 (3)	−0.025 (2)	−0.031 (2)	0.018 (3)
O1	0.0521 (19)	0.047 (2)	0.074 (2)	−0.0301 (16)	−0.0224 (16)	0.0188 (17)
O2	0.097 (3)	0.081 (3)	0.119 (3)	−0.050 (2)	−0.067 (2)	0.045 (2)
C1	0.043 (3)	0.036 (3)	0.041 (2)	−0.011 (2)	−0.011 (2)	0.004 (2)
C2	0.041 (3)	0.031 (3)	0.037 (2)	−0.014 (2)	−0.0074 (19)	0.004 (2)
C3	0.041 (3)	0.034 (3)	0.038 (2)	−0.011 (2)	0.000 (2)	0.004 (2)
C4	0.038 (2)	0.040 (3)	0.042 (2)	−0.014 (2)	−0.008 (2)	0.008 (2)
C5	0.038 (3)	0.040 (3)	0.045 (3)	−0.007 (2)	−0.009 (2)	0.008 (2)
C6	0.047 (3)	0.041 (3)	0.041 (3)	−0.013 (2)	−0.006 (2)	0.007 (2)
C7	0.046 (3)	0.043 (3)	0.055 (3)	−0.015 (2)	−0.008 (2)	0.013 (2)
C8	0.040 (3)	0.034 (3)	0.045 (3)	−0.014 (2)	−0.005 (2)	0.007 (2)
C9	0.052 (3)	0.040 (3)	0.065 (3)	−0.005 (2)	−0.004 (2)	0.009 (3)
C10	0.052 (3)	0.050 (3)	0.077 (4)	0.006 (3)	−0.005 (3)	0.009 (3)
C11	0.072 (4)	0.045 (3)	0.057 (3)	−0.004 (3)	−0.018 (3)	0.016 (3)
C12	0.064 (3)	0.046 (3)	0.042 (3)	−0.023 (3)	−0.010 (2)	0.012 (2)
C13	0.043 (3)	0.042 (3)	0.045 (3)	−0.012 (2)	−0.010 (2)	0.008 (2)
C14	0.103 (4)	0.058 (4)	0.078 (4)	−0.023 (3)	−0.027 (3)	0.010 (3)
C15	0.085 (4)	0.074 (4)	0.115 (5)	−0.020 (3)	−0.036 (3)	−0.014 (4)

Cl1—C11	1.728 (4)	C4—C7	1.435 (5)
N1—C1	1.372 (4)	C8—C9	1.388 (5)
N1—C5	1.377 (4)	C8—C13	1.401 (5)
N1—H1	0.8600	C9—C10	1.385 (5)
N2—C1	1.323 (4)	C9—H9	0.9300
N2—H2A	0.8600	C10—C11	1.380 (6)
N2—H2B	0.8600	C10—H10	0.9300
N3—C6	1.147 (5)	C11—C12	1.374 (6)
N4—C7	1.152 (5)	C12—C13	1.377 (5)
O1—C5	1.255 (4)	C12—H12	0.9300
O2—C14	1.396 (5)	C13—H13	0.9300
O2—H2	0.8200	C14—C15	1.497 (6)
C1—C2	1.404 (5)	C14—H14A	0.9700
C2—C3	1.407 (5)	C14—H14B	0.9700
C2—C6	1.432 (5)	C15—H15A	0.9600
C3—C4	1.395 (5)	C15—H15B	0.9600
C3—C8	1.479 (5)	C15—H15C	0.9600
C4—C5	1.429 (5)
C1—N1—C5	124.9 (3)	C10—C9—C8	120.0 (4)
C1—N1—H1	117.5	C10—C9—H9	120.0
C5—N1—H1	117.5	C8—C9—H9	120.0
C1—N2—H2A	120.0	C11—C10—C9	120.7 (4)
C1—N2—H2B	120.0	C11—C10—H10	119.6
H2A—N2—H2B	120.0	C9—C10—H10	119.6
C14—O2—H2	109.5	C12—C11—C10	119.7 (4)
N2—C1—N1	118.0 (4)	C12—C11—Cl1	120.5 (4)
N2—C1—C2	124.1 (4)	C10—C11—Cl1	119.8 (4)
N1—C1—C2	117.9 (4)	C11—C12—C13	120.2 (4)
C1—C2—C3	120.7 (4)	C11—C12—H12	119.9
C1—C2—C6	118.1 (3)	C13—C12—H12	119.9
C3—C2—C6	121.1 (4)	C12—C13—C8	120.8 (4)
C4—C3—C2	118.4 (4)	C12—C13—H13	119.6
C4—C3—C8	122.5 (3)	C8—C13—H13	119.6
C2—C3—C8	119.1 (4)	O2—C14—C15	109.8 (4)
C3—C4—C5	121.8 (4)	O2—C14—H14A	109.7
C3—C4—C7	122.4 (4)	C15—C14—H14A	109.7
C5—C4—C7	115.7 (4)	O2—C14—H14B	109.7
O1—C5—N1	118.8 (4)	C15—C14—H14B	109.7
O1—C5—C4	125.3 (4)	H14A—C14—H14B	108.2
N1—C5—C4	115.9 (4)	C14—C15—H15A	109.5
N3—C6—C2	177.2 (5)	C14—C15—H15B	109.5
N4—C7—C4	178.7 (5)	H15A—C15—H15B	109.5
C9—C8—C13	118.5 (4)	C14—C15—H15C	109.5
C9—C8—C3	121.9 (4)	H15A—C15—H15C	109.5
C13—C8—C3	119.7 (4)	H15B—C15—H15C	109.5
C5—N1—C1—N2	179.8 (4)	C7—C4—C5—O1	−1.2 (6)
C5—N1—C1—C2	−0.3 (6)	C3—C4—C5—N1	−1.0 (6)
N2—C1—C2—C3	174.8 (4)	C7—C4—C5—N1	177.1 (4)
N1—C1—C2—C3	−5.0 (6)	C4—C3—C8—C9	52.2 (6)
N2—C1—C2—C6	−8.4 (6)	C2—C3—C8—C9	−128.5 (4)
N1—C1—C2—C6	171.8 (3)	C4—C3—C8—C13	−127.0 (4)
C1—C2—C3—C4	7.1 (6)	C2—C3—C8—C13	52.4 (5)
C6—C2—C3—C4	−169.6 (4)	C13—C8—C9—C10	−1.9 (6)
C1—C2—C3—C8	−172.3 (4)	C3—C8—C9—C10	178.9 (4)
C6—C2—C3—C8	11.0 (6)	C8—C9—C10—C11	0.4 (7)
C2—C3—C4—C5	−4.0 (6)	C9—C10—C11—C12	1.6 (7)
C8—C3—C4—C5	175.4 (4)	C9—C10—C11—Cl1	−179.0 (4)
C2—C3—C4—C7	178.1 (4)	C10—C11—C12—C13	−2.2 (7)
C8—C3—C4—C7	−2.5 (6)	Cl1—C11—C12—C13	178.5 (3)
C1—N1—C5—O1	−178.4 (4)	C11—C12—C13—C8	0.7 (6)
C1—N1—C5—C4	3.3 (6)	C9—C8—C13—C12	1.3 (6)
C3—C4—C5—O1	−179.2 (4)	C3—C8—C13—C12	−179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.02	2.755 (4)	149
N2—H2B···N3ii	0.86	2.25	3.084 (5)	164
N2—H2A···O2iii	0.86	1.98	2.832 (4)	168
N1—H1···O1iv	0.86	2.00	2.849 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.02	2.755 (4)	149
N2—H2B⋯N3ii	0.86	2.25	3.084 (5)	164
N2—H2A⋯O2iii	0.86	1.98	2.832 (4)	168
N1—H1⋯O1iv	0.86	2.00	2.849 (4)	171

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