(E)-2-[4-(2-Chloro-phen-yl)but-3-en-2-yl-idene]malononitrile.

There are two independent but virtually identical mol-ecules in the asymmetric unit of the title compound, C(13)H(19)ClN(2). Each mol-ecular skeleton displays an approximately planar structure except for the methyl group [the r.m.s. deviations for all 16 non-H atoms are 0.039 (mol-ecule 1) and 0.056 Å (mol-ecule 2)]. An E configuration is found about each of the C=C bonds. The crystal packing is stabilized by C-H⋯N inter-actions that connect the independent mol-ecules into supra-molecular chains along the c-axis direction.

Related literature

For the use of malononitrile-containing compounds as building blocks in synthesis, see: Liu et al. (2002 ▶); Sepiol & Milart (1985 ▶); Zhang et al. (2003 ▶). For a related structure, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C13H9ClN2

M = 228.67

Triclinic,

a = 7.7177 (2) Å

b = 11.0539 (5) Å

c = 14.7236 (5) Å

α = 91.260 (3)°

β = 103.992 (3)°

γ = 106.357 (3)°

V = 1163.99 (7) Å3

Z = 4

Cu Kα radiation

μ = 2.67 mm−1

T = 291 K

0.35 × 0.32 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.455, T max = 0.502

9739 measured reflections

4135 independent reflections

3770 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.04

4135 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037159/tk2789sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037159/tk2789Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037159/tk2789Isup3.cml

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

C13H9ClN2	Z = 4
Mr = 228.67	F(000) = 472
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.7177 (2) Å	Cell parameters from 6315 reflections
b = 11.0539 (5) Å	θ = 3.1–72.1°
c = 14.7236 (5) Å	µ = 2.67 mm−1
α = 91.260 (3)°	T = 291 K
β = 103.992 (3)°	Block, yellow
γ = 106.357 (3)°	0.35 × 0.32 × 0.30 mm
V = 1163.99 (7) Å3

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4135 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3770 reflections with I > 2σ(I)
mirror	Rint = 0.027
Detector resolution: 15.9149 pixels mm-1	θmax = 67.1°, θmin = 3.1°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.455, Tmax = 0.502	l = −17→17
9739 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.290P] where P = (Fo2 + 2Fc2)/3
4135 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.20 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
C24	0.5347 (2)	0.25777 (17)	0.36952 (12)	0.0541 (4)
C9	0.6600 (2)	0.30400 (18)	0.94779 (12)	0.0536 (4)
C8	0.6947 (3)	0.43885 (18)	0.96046 (13)	0.0562 (4)
H8	0.6495	0.4786	0.9088	0.067*
C1	0.9378 (3)	0.71648 (18)	1.14140 (13)	0.0569 (4)
C23	0.5469 (3)	0.2649 (2)	0.53865 (14)	0.0670 (5)
H23A	0.4703	0.1791	0.5194	0.100*
H23C	0.4796	0.3106	0.5656	0.100*
H23B	0.6592	0.2654	0.5846	0.100*
C22	0.5964 (3)	0.32662 (18)	0.45502 (13)	0.0551 (4)
N1	0.4827 (4)	−0.0031 (2)	0.83682 (16)	0.0942 (7)
C11	0.5561 (3)	0.23861 (18)	0.86407 (13)	0.0574 (4)
C19	0.8945 (3)	0.66283 (18)	0.55896 (14)	0.0588 (5)
C6	0.8253 (2)	0.64747 (17)	1.05665 (12)	0.0524 (4)
C26	0.4247 (3)	0.1281 (2)	0.35739 (15)	0.0697 (5)
C12	0.5155 (3)	0.1042 (2)	0.84862 (15)	0.0679 (5)
C25	0.5774 (3)	0.30988 (19)	0.28661 (13)	0.0600 (5)
C14	0.9546 (3)	0.7332 (2)	0.64619 (15)	0.0651 (5)
C5	0.7504 (3)	0.71784 (19)	0.98811 (14)	0.0613 (5)
H5	0.6738	0.6759	0.9307	0.074*
C4	0.7863 (3)	0.8465 (2)	1.00278 (17)	0.0716 (6)
H4	0.7347	0.8903	0.9557	0.086*
N2	0.4120 (3)	0.3468 (2)	0.72447 (14)	0.0907 (6)
C10	0.7382 (3)	0.2352 (2)	1.02658 (14)	0.0645 (5)
H10A	0.6969	0.1460	1.0073	0.097*
H10C	0.6955	0.2506	1.0806	0.097*
H10B	0.8723	0.2650	1.0423	0.097*
C20	0.7793 (3)	0.53241 (19)	0.54577 (13)	0.0594 (5)
H20	0.7489	0.4972	0.5987	0.071*
C21	0.7120 (3)	0.45749 (18)	0.46499 (13)	0.0577 (4)
H21	0.7412	0.4915	0.4114	0.069*
C7	0.7870 (2)	0.51104 (18)	1.04108 (13)	0.0544 (4)
H7	0.8312	0.4701	1.0922	0.065*
C18	0.9567 (3)	0.7248 (2)	0.48501 (16)	0.0703 (5)
H18	0.9197	0.6815	0.4254	0.084*
C17	1.0704 (3)	0.8474 (2)	0.4987 (2)	0.0855 (7)
H17	1.1080	0.8863	0.4484	0.103*
C2	0.9749 (3)	0.8458 (2)	1.15697 (17)	0.0730 (6)
H2	1.0507	0.8888	1.2142	0.088*
C13	0.4755 (3)	0.2988 (2)	0.78642 (14)	0.0661 (5)
C15	1.0718 (3)	0.8564 (2)	0.6601 (2)	0.0844 (7)
H15	1.1119	0.9008	0.7194	0.101*
C3	0.8988 (3)	0.9107 (2)	1.08720 (19)	0.0776 (6)
H3	0.9233	0.9980	1.0971	0.093*
C16	1.1285 (4)	0.9126 (3)	0.5857 (3)	0.0941 (8)
H16	1.2068	0.9954	0.5947	0.113*
N3	0.6097 (3)	0.3519 (2)	0.22018 (13)	0.0802 (5)
N4	0.3349 (4)	0.0253 (2)	0.34942 (17)	0.1014 (8)
Cl1	1.03787 (8)	0.63948 (6)	1.23196 (4)	0.0778 (2)
Cl2	0.88209 (9)	0.66910 (6)	0.74273 (4)	0.0836 (2)

	U11	U22	U33	U12	U13	U23
C24	0.0527 (9)	0.0603 (10)	0.0449 (9)	0.0145 (8)	0.0070 (7)	0.0042 (8)
C9	0.0564 (10)	0.0620 (10)	0.0417 (9)	0.0157 (8)	0.0137 (8)	0.0040 (7)
C8	0.0603 (10)	0.0620 (11)	0.0433 (9)	0.0149 (8)	0.0113 (8)	0.0084 (8)
C1	0.0525 (9)	0.0617 (11)	0.0491 (10)	0.0086 (8)	0.0089 (8)	0.0051 (8)
C23	0.0747 (12)	0.0774 (13)	0.0473 (10)	0.0197 (10)	0.0156 (9)	0.0124 (9)
C22	0.0581 (10)	0.0639 (11)	0.0451 (9)	0.0240 (8)	0.0093 (8)	0.0088 (8)
N1	0.1175 (17)	0.0700 (13)	0.0813 (14)	0.0206 (12)	0.0100 (12)	−0.0096 (11)
C11	0.0626 (10)	0.0653 (11)	0.0435 (9)	0.0187 (9)	0.0129 (8)	0.0020 (8)
C19	0.0597 (10)	0.0621 (11)	0.0544 (11)	0.0267 (9)	0.0044 (8)	0.0055 (8)
C6	0.0483 (9)	0.0575 (10)	0.0474 (9)	0.0100 (7)	0.0115 (7)	0.0075 (7)
C26	0.0694 (12)	0.0719 (14)	0.0546 (11)	0.0062 (10)	0.0094 (10)	0.0008 (9)
C12	0.0750 (13)	0.0696 (13)	0.0526 (11)	0.0178 (10)	0.0094 (10)	−0.0039 (9)
C25	0.0649 (11)	0.0634 (11)	0.0440 (10)	0.0142 (9)	0.0062 (8)	−0.0008 (8)
C14	0.0636 (11)	0.0714 (12)	0.0598 (11)	0.0322 (10)	0.0011 (9)	0.0005 (9)
C5	0.0567 (10)	0.0682 (12)	0.0538 (11)	0.0139 (9)	0.0093 (8)	0.0133 (9)
C4	0.0713 (13)	0.0674 (13)	0.0790 (15)	0.0220 (10)	0.0216 (11)	0.0246 (11)
N2	0.1135 (16)	0.1141 (17)	0.0487 (11)	0.0514 (14)	0.0078 (10)	0.0067 (10)
C10	0.0774 (13)	0.0643 (12)	0.0482 (10)	0.0223 (10)	0.0082 (9)	0.0066 (9)
C20	0.0618 (11)	0.0675 (11)	0.0475 (10)	0.0225 (9)	0.0074 (8)	0.0068 (8)
C21	0.0598 (10)	0.0646 (11)	0.0473 (10)	0.0191 (9)	0.0102 (8)	0.0077 (8)
C7	0.0527 (9)	0.0619 (11)	0.0448 (9)	0.0133 (8)	0.0094 (7)	0.0065 (8)
C18	0.0731 (13)	0.0788 (14)	0.0644 (13)	0.0338 (11)	0.0136 (10)	0.0138 (10)
C17	0.0732 (14)	0.0788 (16)	0.110 (2)	0.0272 (12)	0.0273 (14)	0.0291 (15)
C2	0.0726 (13)	0.0618 (12)	0.0689 (13)	0.0011 (10)	0.0125 (11)	−0.0047 (10)
C13	0.0773 (13)	0.0785 (13)	0.0411 (10)	0.0257 (11)	0.0104 (9)	−0.0009 (9)
C15	0.0735 (14)	0.0753 (15)	0.0921 (18)	0.0239 (12)	−0.0022 (13)	−0.0113 (13)
C3	0.0828 (15)	0.0555 (12)	0.0920 (17)	0.0122 (10)	0.0276 (13)	0.0094 (11)
C16	0.0732 (15)	0.0717 (15)	0.127 (3)	0.0179 (12)	0.0117 (16)	0.0060 (16)
N3	0.0992 (14)	0.0858 (13)	0.0485 (10)	0.0164 (11)	0.0189 (9)	0.0050 (9)
N4	0.1103 (17)	0.0789 (14)	0.0845 (15)	−0.0136 (13)	0.0191 (13)	−0.0043 (11)
Cl1	0.0806 (4)	0.0843 (4)	0.0513 (3)	0.0177 (3)	−0.0067 (2)	0.0067 (2)
Cl2	0.0973 (4)	0.1005 (5)	0.0477 (3)	0.0347 (3)	0.0035 (3)	−0.0035 (3)

C24—C22	1.362 (3)	C25—N3	1.144 (3)
C24—C26	1.427 (3)	C14—C15	1.386 (3)
C24—C25	1.432 (3)	C14—Cl2	1.744 (2)
C9—C11	1.357 (3)	C5—C4	1.372 (3)
C9—C8	1.438 (3)	C5—H5	0.9300
C9—C10	1.499 (3)	C4—C3	1.377 (3)
C8—C7	1.335 (3)	C4—H4	0.9300
C8—H8	0.9300	N2—C13	1.143 (3)
C1—C2	1.379 (3)	C10—H10A	0.9600
C1—C6	1.398 (3)	C10—H10C	0.9600
C1—Cl1	1.738 (2)	C10—H10B	0.9600
C23—C22	1.498 (3)	C20—C21	1.336 (3)
C23—H23A	0.9600	C20—H20	0.9300
C23—H23C	0.9600	C21—H21	0.9300
C23—H23B	0.9600	C7—H7	0.9300
C22—C21	1.453 (3)	C18—C17	1.370 (3)
N1—C12	1.141 (3)	C18—H18	0.9300
C11—C12	1.430 (3)	C17—C16	1.365 (4)
C11—C13	1.435 (3)	C17—H17	0.9300
C19—C14	1.391 (3)	C2—C3	1.376 (3)
C19—C18	1.409 (3)	C2—H2	0.9300
C19—C20	1.445 (3)	C15—C16	1.372 (4)
C6—C5	1.401 (3)	C15—H15	0.9300
C6—C7	1.454 (3)	C3—H3	0.9300
C26—N4	1.139 (3)	C16—H16	0.9300
C22—C24—C26	121.80 (17)	C6—C5—H5	118.9
C22—C24—C25	122.40 (17)	C5—C4—C3	120.0 (2)
C26—C24—C25	115.80 (17)	C5—C4—H4	120.0
C11—C9—C8	119.85 (17)	C3—C4—H4	120.0
C11—C9—C10	119.80 (18)	C9—C10—H10A	109.5
C8—C9—C10	120.35 (16)	C9—C10—H10C	109.5
C7—C8—C9	124.63 (17)	H10A—C10—H10C	109.5
C7—C8—H8	117.7	C9—C10—H10B	109.5
C9—C8—H8	117.7	H10A—C10—H10B	109.5
C2—C1—C6	122.53 (19)	H10C—C10—H10B	109.5
C2—C1—Cl1	117.46 (16)	C21—C20—C19	126.43 (19)
C6—C1—Cl1	120.01 (15)	C21—C20—H20	116.8
C22—C23—H23A	109.5	C19—C20—H20	116.8
C22—C23—H23C	109.5	C20—C21—C22	124.53 (18)
H23A—C23—H23C	109.5	C20—C21—H21	117.7
C22—C23—H23B	109.5	C22—C21—H21	117.7
H23A—C23—H23B	109.5	C8—C7—C6	126.29 (17)
H23C—C23—H23B	109.5	C8—C7—H7	116.9
C24—C22—C21	120.17 (17)	C6—C7—H7	116.9
C24—C22—C23	119.18 (18)	C17—C18—C19	121.7 (2)
C21—C22—C23	120.64 (17)	C17—C18—H18	119.1
C9—C11—C12	121.86 (18)	C19—C18—H18	119.1
C9—C11—C13	122.42 (18)	C16—C17—C18	120.3 (3)
C12—C11—C13	115.70 (18)	C16—C17—H17	119.9
C14—C19—C18	116.2 (2)	C18—C17—H17	119.9
C14—C19—C20	121.75 (19)	C3—C2—C1	119.5 (2)
C18—C19—C20	122.03 (19)	C3—C2—H2	120.3
C1—C6—C5	115.78 (18)	C1—C2—H2	120.3
C1—C6—C7	122.04 (17)	N2—C13—C11	179.7 (2)
C5—C6—C7	122.18 (17)	C16—C15—C14	119.6 (3)
N4—C26—C24	178.2 (3)	C16—C15—H15	120.2
N1—C12—C11	179.5 (3)	C14—C15—H15	120.2
N3—C25—C24	179.2 (2)	C2—C3—C4	120.0 (2)
C15—C14—C19	121.9 (2)	C2—C3—H3	120.0
C15—C14—Cl2	117.28 (19)	C4—C3—H3	120.0
C19—C14—Cl2	120.77 (17)	C17—C16—C15	120.3 (2)
C4—C5—C6	122.21 (19)	C17—C16—H16	119.9
C4—C5—H5	118.9	C15—C16—H16	119.9
C11—C9—C8—C7	176.58 (19)	C1—C6—C5—C4	0.6 (3)
C10—C9—C8—C7	−3.4 (3)	C7—C6—C5—C4	179.95 (18)
C26—C24—C22—C21	178.43 (18)	C6—C5—C4—C3	−0.3 (3)
C25—C24—C22—C21	−0.8 (3)	C14—C19—C20—C21	178.88 (19)
C26—C24—C22—C23	−0.3 (3)	C18—C19—C20—C21	−2.9 (3)
C25—C24—C22—C23	−179.49 (18)	C19—C20—C21—C22	−179.99 (17)
C8—C9—C11—C12	−179.02 (18)	C24—C22—C21—C20	−179.91 (19)
C10—C9—C11—C12	1.0 (3)	C23—C22—C21—C20	−1.2 (3)
C8—C9—C11—C13	−0.8 (3)	C9—C8—C7—C6	179.82 (17)
C10—C9—C11—C13	179.17 (19)	C1—C6—C7—C8	−174.14 (19)
C2—C1—C6—C5	−0.6 (3)	C5—C6—C7—C8	6.5 (3)
Cl1—C1—C6—C5	179.76 (14)	C14—C19—C18—C17	0.2 (3)
C2—C1—C6—C7	−179.94 (18)	C20—C19—C18—C17	−178.10 (19)
Cl1—C1—C6—C7	0.4 (3)	C19—C18—C17—C16	0.8 (3)
C22—C24—C26—N4	35 (9)	C6—C1—C2—C3	0.2 (3)
C25—C24—C26—N4	−146 (9)	Cl1—C1—C2—C3	179.92 (18)
C9—C11—C12—N1	56 (43)	C9—C11—C13—N2	85 (47)
C13—C11—C12—N1	−122 (43)	C12—C11—C13—N2	−96 (47)
C22—C24—C25—N3	−90 (17)	C19—C14—C15—C16	1.2 (3)
C26—C24—C25—N3	91 (17)	Cl2—C14—C15—C16	−178.09 (19)
C18—C19—C14—C15	−1.2 (3)	C1—C2—C3—C4	0.1 (4)
C20—C19—C14—C15	177.10 (19)	C5—C4—C3—C2	−0.1 (4)
C18—C19—C14—Cl2	178.12 (14)	C18—C17—C16—C15	−0.8 (4)
C20—C19—C14—Cl2	−3.6 (3)	C14—C15—C16—C17	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N3i	0.96	2.62	3.564 (3)	166.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯N3i	0.96	2.62	3.564 (3)	166 (1)

Symmetry code: (i) .