The azo–en­amino­ne 4-(E)-amino-3-[(E)-2-chloro­phenyl­diazenyl]pent-3-en-2-one

The title compound, C₁₁H₁₂ClN₃O, is composed of a planar azoen­amine skeleton, which forms a six-membered ring through an intramolecular hydrogen bond. In the solid state only the azoen­amine tautomer was observed. The molecular packing is through adjacent mol­ecules linked by N—H...O bonds, resulting in a two-dimensional sheet structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.185
• Data-to-parameter ratio = 13.3

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Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

4-(E)-amino-3-[(E)-2-chlorophenylazo]-3-penten-2-one

Crystal data

C11H12ClN3O	F(000) = 496
Mr = 237.69	Dx = 1.377 Mg m^−3
Monoclinic, P21/c	Melting point = 462–464 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 7.673 (6) Å	Cell parameters from 25 reflections
b = 12.887 (1) Å	θ = 11.6–30.0°
c = 11.598 (1) Å	µ = 2.81 mm^−1
β = 91.28 (2)°	T = 293 K
V = 1146.5 (9) Å^3	Irregular, pale yellow
Z = 4	0.35 × 0.13 × 0.12 mm

Data collection

Nonius CAD-4 diffractometer	1756 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 67.0°, θmin = 5.1°
ω–2θ scans	h = −9→8
Absorption correction: ψ scan North, Phillips & Mathews (1968)	k = 0→15
Tmin = 0.649, Tmax = 0.714	l = −1→13
2335 measured reflections	3 standard reflections every 120 min
2038 independent reflections	intensity decay: <1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.1286P)^2 + 0.3565P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2038 reflections	Δρmax = 0.50 e Å^−3
153 parameters	Δρmin = −0.49 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.76190 (10)	0.75900 (5)	0.07214 (6)	0.0604 (4)
N1	0.5838 (3)	0.59484 (17)	−0.1783 (2)	0.0528 (6)
N2	0.7365 (2)	0.44633 (15)	−0.02338 (16)	0.0410 (5)
N3	0.7441 (3)	0.54109 (15)	0.00814 (16)	0.0437 (5)
O1	0.6051 (3)	0.27355 (15)	−0.24254 (17)	0.0628 (6)
C1	0.7304 (4)	0.2404 (2)	−0.0583 (3)	0.0589 (8)
H1A	0.7211	0.1698	−0.0840	0.088*
H1B	0.6634	0.2495	0.0099	0.088*
H1C	0.8504	0.2565	−0.0412	0.088*
C2	0.6619 (3)	0.31199 (19)	−0.1518 (2)	0.0445 (6)
C3	0.6642 (3)	0.42316 (19)	−0.12936 (18)	0.0406 (6)
C4	0.5927 (3)	0.49726 (19)	−0.2081 (2)	0.0432 (6)
C5	0.5275 (4)	0.4708 (2)	−0.3268 (2)	0.0568 (7)
H5A	0.4905	0.5330	−0.3658	0.085*
H5B	0.4308	0.4238	−0.3219	0.085*
H5C	0.6192	0.4386	−0.3689	0.085*
C6	0.8233 (3)	0.55584 (19)	0.11834 (19)	0.0431 (6)
C7	0.8875 (4)	0.4765 (2)	0.1883 (2)	0.0523 (7)
H7	0.8799	0.4081	0.1633	0.063*
C8	0.9627 (4)	0.4986 (2)	0.2949 (2)	0.0587 (7)
H8	1.0067	0.4450	0.3407	0.070*
C9	0.9729 (4)	0.5993 (3)	0.3338 (2)	0.0610 (8)
H9	1.0226	0.6134	0.4060	0.073*
C10	0.9096 (4)	0.6793 (2)	0.2662 (2)	0.0578 (7)
H10	0.9158	0.7474	0.2926	0.069*
C11	0.8369 (3)	0.65778 (19)	0.1588 (2)	0.0465 (6)
H1	0.537 (4)	0.638 (2)	−0.220 (3)	0.056*
H2	0.626 (4)	0.609 (2)	−0.104 (3)	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0763 (6)	0.0392 (5)	0.0660 (5)	−0.0016 (3)	0.0057 (3)	−0.0006 (3)
N1	0.0707 (15)	0.0389 (12)	0.0485 (12)	0.0069 (10)	−0.0038 (10)	0.0043 (9)
N2	0.0441 (10)	0.0371 (11)	0.0419 (10)	−0.0001 (8)	0.0049 (8)	−0.0017 (8)
N3	0.0528 (12)	0.0352 (11)	0.0432 (11)	0.0019 (8)	0.0021 (8)	−0.0033 (8)
O1	0.0869 (15)	0.0459 (12)	0.0552 (11)	−0.0094 (9)	−0.0064 (10)	−0.0093 (8)
C1	0.0722 (19)	0.0370 (16)	0.0673 (18)	0.0036 (11)	−0.0037 (14)	0.0019 (11)
C2	0.0461 (13)	0.0399 (14)	0.0477 (13)	−0.0014 (9)	0.0050 (10)	−0.0032 (10)
C3	0.0436 (12)	0.0392 (13)	0.0391 (11)	0.0021 (9)	0.0043 (9)	−0.0010 (9)
C4	0.0437 (12)	0.0426 (14)	0.0433 (12)	0.0009 (9)	0.0054 (10)	0.0023 (9)
C5	0.0681 (17)	0.0561 (17)	0.0459 (14)	0.0046 (13)	−0.0044 (12)	0.0010 (11)
C6	0.0456 (12)	0.0419 (13)	0.0421 (12)	−0.0007 (9)	0.0060 (9)	−0.0028 (9)
C7	0.0620 (15)	0.0449 (15)	0.0497 (14)	0.0028 (11)	−0.0009 (11)	−0.0016 (11)
C8	0.0590 (16)	0.0663 (19)	0.0506 (15)	0.0035 (13)	−0.0034 (12)	0.0021 (12)
C9	0.0586 (16)	0.076 (2)	0.0483 (14)	−0.0071 (13)	−0.0039 (11)	−0.0087 (13)
C10	0.0619 (16)	0.0577 (17)	0.0540 (15)	−0.0104 (12)	0.0050 (12)	−0.0167 (12)
C11	0.0477 (13)	0.0423 (14)	0.0500 (13)	−0.0038 (10)	0.0088 (10)	−0.0047 (10)

Geometric parameters (Å, º)

Cl—C11	1.737 (3)	C4—C5	1.494 (3)
N1—C4	1.306 (3)	C5—H5A	0.9600
N1—H1	0.82 (3)	C5—H5B	0.9600
N1—H2	0.94 (3)	C5—H5C	0.9600
N2—N3	1.276 (3)	C6—C7	1.389 (4)
N2—C3	1.370 (3)	C6—C11	1.398 (3)
N3—C6	1.416 (3)	C7—C8	1.382 (4)
O1—C2	1.234 (3)	C7—H7	0.9300
C1—C2	1.509 (4)	C8—C9	1.376 (4)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.378 (4)
C1—H1C	0.9600	C9—H9	0.9300
C2—C3	1.456 (3)	C10—C11	1.381 (4)
C3—C4	1.423 (3)	C10—H10	0.9300
C4—N1—H1	121 (2)	H5A—C5—H5B	109.5
C4—N1—H2	114.4 (19)	C4—C5—H5C	109.5
H1—N1—H2	124 (3)	H5A—C5—H5C	109.5
N3—N2—C3	118.7 (2)	H5B—C5—H5C	109.5
N2—N3—C6	113.78 (19)	C7—C6—C11	118.2 (2)
C2—C1—H1A	109.5	C7—C6—N3	124.6 (2)
C2—C1—H1B	109.5	C11—C6—N3	117.2 (2)
H1A—C1—H1B	109.5	C8—C7—C6	120.5 (3)
C2—C1—H1C	109.5	C8—C7—H7	119.8
H1A—C1—H1C	109.5	C6—C7—H7	119.8
H1B—C1—H1C	109.5	C9—C8—C7	120.5 (3)
O1—C2—C3	123.4 (2)	C9—C8—H8	119.8
O1—C2—C1	118.6 (2)	C7—C8—H8	119.8
C3—C2—C1	118.0 (2)	C8—C9—C10	120.2 (2)
N2—C3—C4	124.9 (2)	C8—C9—H9	119.9
N2—C3—C2	112.2 (2)	C10—C9—H9	119.9
C4—C3—C2	122.9 (2)	C9—C10—C11	119.6 (3)
N1—C4—C3	119.9 (2)	C9—C10—H10	120.2
N1—C4—C5	116.4 (2)	C11—C10—H10	120.2
C3—C4—C5	123.7 (2)	C10—C11—C6	121.1 (2)
C4—C5—H5A	109.5	C10—C11—Cl	119.5 (2)
C4—C5—H5B	109.5	C6—C11—Cl	119.36 (19)
C3—N2—N3—C6	−179.21 (18)	N2—N3—C6—C11	179.8 (2)
N3—N2—C3—C4	−1.2 (3)	C11—C6—C7—C8	0.0 (4)
N3—N2—C3—C2	−178.9 (2)	N3—C6—C7—C8	−179.9 (2)
O1—C2—C3—N2	−179.0 (2)	C6—C7—C8—C9	0.9 (4)
C1—C2—C3—N2	2.0 (3)	C7—C8—C9—C10	−0.7 (4)
O1—C2—C3—C4	3.3 (4)	C8—C9—C10—C11	−0.4 (4)
C1—C2—C3—C4	−175.8 (2)	C9—C10—C11—C6	1.2 (4)
N2—C3—C4—N1	−4.0 (4)	C9—C10—C11—Cl	−178.5 (2)
C2—C3—C4—N1	173.5 (2)	C7—C6—C11—C10	−1.0 (4)
N2—C3—C4—C5	175.0 (2)	N3—C6—C11—C10	178.9 (2)
C2—C3—C4—C5	−7.5 (4)	C7—C6—C11—Cl	178.68 (18)
N2—N3—C6—C7	−0.3 (3)	N3—C6—C11—Cl	−1.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···N3	0.94 (3)	1.79 (3)	2.559 (3)	137 (3)
N1—H1···O1^i	0.82 (3)	2.10 (3)	2.862 (3)	155 (3)

Symmetry code: (i) −x+1, y+1/2, −z−1/2.