4-Chloro-N-(3-phenyl-allyl-idene)aniline.

In the title mol-ecule, C(15)H(12)ClN, the C=N and C=C bond lengths are 1.273 (2) and 1.324 (2) Å, respectively. The two aromatic rings form a dihedral angle of 3.27 (3)°.

Related literature

For a related structure, see Pu (2008 ▶). For general background, see: Garnovskii et al. (1993 ▶); Anderson et al. (1997 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12ClN

M = 241.71

Orthorhombic,

a = 7.7333 (7) Å

b = 5.5957 (5) Å

c = 29.383 (3) Å

V = 1271.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 295 (2) K

0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.960, T max = 0.978

6043 measured reflections

2187 independent reflections

2042 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.05

2187 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1031 Friedel pairs

Flack parameter: 0.07 (5)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039391/cv2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039391/cv2477Isup2.hkl

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

C15H12ClN	F000 = 504
Mr = 241.71	Dx = 1.263 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3328 reflections
a = 7.7333 (7) Å	θ = 2.7–27.2º
b = 5.5957 (5) Å	µ = 0.28 mm−1
c = 29.383 (3) Å	T = 295 (2) K
V = 1271.5 (2) Å3	Block, yellow
Z = 4	0.15 × 0.12 × 0.08 mm

Bruker APEXII CCD area-detector diffractometer	2187 independent reflections
Radiation source: fine-focus sealed tube	2042 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 295(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.960, Tmax = 0.978	k = −6→4
6043 measured reflections	l = −32→35

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.0706P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.09 e Å−3
2187 reflections	Δρmin = −0.15 e Å−3
154 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1031 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.07 (5)

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	0.65759 (7)	0.44278 (11)	0.969692 (18)	0.08065 (18)
N1	0.87735 (18)	0.5317 (3)	0.77774 (5)	0.0522 (3)
C1	0.7249 (2)	0.4739 (3)	0.91350 (6)	0.0509 (4)
C2	0.8238 (2)	0.6663 (3)	0.90138 (5)	0.0535 (4)
H2	0.8555	0.7795	0.9230	0.064*
C3	0.8761 (2)	0.6907 (3)	0.85660 (5)	0.0503 (4)
H3	0.9443	0.8203	0.8483	0.060*
C4	0.82813 (19)	0.5241 (3)	0.82396 (6)	0.0430 (3)
C5	0.7294 (2)	0.3300 (3)	0.83740 (6)	0.0483 (4)
H5	0.6984	0.2152	0.8160	0.058*
C6	0.6762 (2)	0.3037 (3)	0.88200 (6)	0.0524 (4)
H6	0.6088	0.1737	0.8906	0.063*
C7	0.9240 (2)	0.7278 (3)	0.75959 (6)	0.0499 (4)
H7	0.9253	0.8657	0.7773	0.060*
C8	0.9747 (2)	0.7431 (3)	0.71272 (5)	0.0477 (3)
H8	0.9650	0.6067	0.6948	0.057*
C9	1.0343 (2)	0.9406 (3)	0.69352 (5)	0.0504 (4)
H9	1.0425	1.0744	0.7122	0.060*
C10	1.0884 (2)	0.9711 (3)	0.64651 (5)	0.0421 (3)
C11	1.1805 (2)	1.1742 (3)	0.63356 (5)	0.0493 (4)
H11	1.2065	1.2901	0.6552	0.059*
C12	1.2339 (2)	1.2059 (3)	0.58897 (6)	0.0541 (4)
H12	1.2960	1.3419	0.5810	0.065*
C13	1.1957 (2)	1.0385 (3)	0.55664 (6)	0.0531 (4)
H13	1.2307	1.0608	0.5267	0.064*
C14	1.1043 (2)	0.8352 (3)	0.56881 (5)	0.0505 (4)
H14	1.0791	0.7201	0.5470	0.061*
C15	1.0509 (2)	0.8028 (3)	0.61284 (5)	0.0452 (3)
H15	0.9886	0.6664	0.6204	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.0921 (4)	0.1047 (4)	0.0451 (2)	−0.0037 (3)	0.0100 (2)	0.0165 (3)
N1	0.0539 (8)	0.0588 (8)	0.0439 (8)	−0.0028 (6)	0.0035 (6)	0.0003 (6)
C1	0.0462 (9)	0.0647 (11)	0.0417 (8)	0.0070 (8)	0.0009 (7)	0.0096 (8)
C2	0.0597 (10)	0.0562 (10)	0.0448 (9)	−0.0048 (8)	−0.0048 (7)	−0.0015 (8)
C3	0.0522 (9)	0.0502 (9)	0.0487 (9)	−0.0114 (8)	−0.0012 (7)	0.0045 (8)
C4	0.0383 (7)	0.0467 (8)	0.0441 (8)	0.0020 (6)	−0.0021 (7)	0.0021 (7)
C5	0.0484 (9)	0.0431 (8)	0.0535 (9)	−0.0021 (7)	0.0010 (7)	−0.0011 (7)
C6	0.0496 (9)	0.0503 (9)	0.0573 (10)	−0.0071 (7)	0.0031 (8)	0.0092 (8)
C7	0.0480 (8)	0.0569 (9)	0.0448 (8)	0.0002 (7)	−0.0011 (7)	0.0019 (7)
C8	0.0464 (8)	0.0556 (9)	0.0412 (7)	−0.0002 (7)	−0.0005 (7)	−0.0001 (6)
C9	0.0534 (9)	0.0527 (9)	0.0450 (8)	−0.0019 (7)	−0.0028 (7)	−0.0021 (7)
C10	0.0392 (7)	0.0449 (8)	0.0423 (8)	0.0034 (6)	−0.0041 (6)	0.0052 (6)
C11	0.0499 (9)	0.0444 (8)	0.0537 (9)	−0.0028 (7)	−0.0055 (7)	0.0005 (7)
C12	0.0515 (10)	0.0483 (9)	0.0625 (11)	−0.0021 (7)	0.0037 (8)	0.0143 (8)
C13	0.0553 (10)	0.0565 (10)	0.0477 (10)	0.0064 (7)	0.0035 (7)	0.0099 (8)
C14	0.0584 (10)	0.0500 (9)	0.0432 (9)	0.0057 (7)	−0.0044 (7)	−0.0017 (7)
C15	0.0481 (8)	0.0426 (7)	0.0449 (8)	−0.0032 (7)	−0.0052 (7)	0.0041 (7)

Cl1—C1	1.7399 (17)	C8—C9	1.324 (2)
N1—C7	1.273 (2)	C8—H8	0.9300
N1—C4	1.411 (2)	C9—C10	1.454 (2)
C1—C2	1.368 (2)	C9—H9	0.9300
C1—C6	1.380 (3)	C10—C11	1.394 (2)
C2—C3	1.383 (2)	C10—C15	1.397 (2)
C2—H2	0.9300	C11—C12	1.385 (2)
C3—C4	1.388 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.367 (3)
C4—C5	1.385 (2)	C12—H12	0.9300
C5—C6	1.382 (2)	C13—C14	1.386 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.370 (2)
C7—C8	1.434 (2)	C14—H14	0.9300
C7—H7	0.9300	C15—H15	0.9300
C7—N1—C4	120.37 (14)	C9—C8—H8	118.2
C2—C1—C6	121.41 (16)	C7—C8—H8	118.2
C2—C1—Cl1	119.54 (14)	C8—C9—C10	127.14 (15)
C6—C1—Cl1	119.05 (14)	C8—C9—H9	116.4
C1—C2—C3	119.25 (16)	C10—C9—H9	116.4
C1—C2—H2	120.4	C11—C10—C15	117.55 (14)
C3—C2—H2	120.4	C11—C10—C9	120.17 (14)
C2—C3—C4	120.87 (15)	C15—C10—C9	122.27 (14)
C2—C3—H3	119.6	C12—C11—C10	121.00 (15)
C4—C3—H3	119.6	C12—C11—H11	119.5
C5—C4—C3	118.49 (15)	C10—C11—H11	119.5
C5—C4—N1	116.52 (14)	C13—C12—C11	120.35 (16)
C3—C4—N1	124.95 (14)	C13—C12—H12	119.8
C6—C5—C4	121.20 (15)	C11—C12—H12	119.8
C6—C5—H5	119.4	C12—C13—C14	119.57 (15)
C4—C5—H5	119.4	C12—C13—H13	120.2
C5—C6—C1	118.77 (15)	C14—C13—H13	120.2
C5—C6—H6	120.6	C15—C14—C13	120.39 (15)
C1—C6—H6	120.6	C15—C14—H14	119.8
N1—C7—C8	122.08 (15)	C13—C14—H14	119.8
N1—C7—H7	119.0	C14—C15—C10	121.14 (14)
C8—C7—H7	119.0	C14—C15—H15	119.4
C9—C8—C7	123.66 (15)	C10—C15—H15	119.4
C6—C1—C2—C3	0.0 (3)	N1—C7—C8—C9	−175.51 (17)
Cl1—C1—C2—C3	−179.67 (13)	C7—C8—C9—C10	179.94 (15)
C1—C2—C3—C4	0.6 (2)	C8—C9—C10—C11	−166.99 (16)
C2—C3—C4—C5	−1.3 (2)	C8—C9—C10—C15	13.3 (3)
C2—C3—C4—N1	−178.92 (16)	C15—C10—C11—C12	−0.6 (2)
C7—N1—C4—C5	160.20 (15)	C9—C10—C11—C12	179.69 (15)
C7—N1—C4—C3	−22.1 (2)	C10—C11—C12—C13	0.5 (3)
C3—C4—C5—C6	1.3 (2)	C11—C12—C13—C14	−0.6 (3)
N1—C4—C5—C6	179.18 (14)	C12—C13—C14—C15	0.7 (2)
C4—C5—C6—C1	−0.7 (2)	C13—C14—C15—C10	−0.7 (2)
C2—C1—C6—C5	0.1 (2)	C11—C10—C15—C14	0.7 (2)
Cl1—C1—C6—C5	179.73 (13)	C9—C10—C15—C14	−179.60 (15)
C4—N1—C7—C8	−179.89 (14)