(E)-1-(4-Amino-phen-yl)-3-(2-chloro-phen-yl)prop-2-en-1-one.

The title compound, C(15)H(12)ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The mol-ecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the mol-ecule is not coplanar with the chloro-phenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent mol-ecules are linked by N-H⋯O inter-actions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.

Related literature

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For bond-length data, see Allen et al. (1987 ▶). For related structures, see, for example: Patil et al. (2007a ▶,b ▶,c ▶). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Gu et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C15H12ClNO

M = 257.71

Monoclinic,

a = 22.4670 (19) Å

b = 3.9254 (3) Å

c = 14.5796 (11) Å

β = 107.944 (6)°

V = 1223.26 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 100.0 (1) K

0.28 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.935, T max = 0.985

12218 measured reflections

2509 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.190

S = 1.13

2509 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.40 e Å−3

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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030456/cs2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030456/cs2093Isup2.hkl

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

C15H12ClNO	F(000) = 536
Mr = 257.71	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2522 reflections
a = 22.4670 (19) Å	θ = 2.9–30.2°
b = 3.9254 (3) Å	µ = 0.30 mm−1
c = 14.5796 (11) Å	T = 100 K
β = 107.944 (6)°	Plate, yellow
V = 1223.26 (17) Å3	0.28 × 0.27 × 0.06 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
graphite	Rint = 0.090
φ and ω scans	θmax = 26.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→28
Tmin = 0.935, Tmax = 0.985	k = −4→4
12218 measured reflections	l = −18→18

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0752P)2 + 2.4541P] where P = (Fo2 + 2Fc2)/3
2509 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

	x	y	z	Uiso*/Ueq
Cl1	0.34916 (5)	0.9235 (3)	0.37527 (7)	0.0286 (3)
O1	0.15206 (14)	0.7004 (9)	0.45043 (19)	0.0269 (8)
N1	0.05603 (19)	0.0034 (9)	0.7731 (3)	0.0191 (8)
C1	0.3762 (2)	1.0766 (12)	0.4936 (3)	0.0209 (9)
C2	0.4360 (2)	1.2147 (12)	0.5233 (3)	0.0253 (10)
H2A	0.4594	1.2283	0.4807	0.030*
C3	0.4604 (2)	1.3321 (12)	0.6171 (3)	0.0252 (10)
H3A	0.5006	1.4230	0.6383	0.030*
C4	0.4246 (2)	1.3131 (12)	0.6790 (3)	0.0249 (10)
H4A	0.4407	1.3939	0.7417	0.030*
C5	0.3654 (2)	1.1761 (12)	0.6487 (3)	0.0224 (10)
H5A	0.3422	1.1667	0.6915	0.027*
C6	0.33907 (19)	1.0500 (11)	0.5547 (3)	0.0190 (9)
C7	0.2757 (2)	0.9108 (11)	0.5222 (3)	0.0209 (9)
H7A	0.2566	0.8946	0.4560	0.025*
C8	0.24290 (19)	0.8055 (11)	0.5784 (3)	0.0206 (10)
H8A	0.2606	0.8178	0.6450	0.025*
C9	0.1783 (2)	0.6678 (11)	0.5372 (3)	0.0199 (9)
C10	0.14809 (19)	0.4951 (11)	0.6006 (3)	0.0180 (9)
C11	0.1771 (2)	0.4548 (11)	0.7004 (3)	0.0195 (9)
H11A	0.2172	0.5414	0.7284	0.023*
C12	0.14740 (19)	0.2898 (11)	0.7572 (3)	0.0199 (9)
H12A	0.1675	0.2655	0.8229	0.024*
C13	0.08702 (19)	0.1580 (10)	0.7165 (3)	0.0169 (9)
C14	0.0572 (2)	0.2036 (11)	0.6173 (3)	0.0187 (9)
H14A	0.0168	0.1229	0.5892	0.022*
C15	0.08799 (19)	0.3678 (11)	0.5619 (3)	0.0198 (10)
H15A	0.0678	0.3944	0.4962	0.024*
H1N1	0.027 (2)	−0.133 (12)	0.745 (3)	0.010 (11)*
H2N1	0.081 (2)	−0.044 (11)	0.827 (3)	0.016 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0359 (7)	0.0389 (7)	0.0140 (5)	−0.0011 (6)	0.0120 (4)	0.0004 (5)
O1	0.0299 (17)	0.040 (2)	0.0094 (14)	−0.0045 (15)	0.0036 (12)	0.0015 (13)
N1	0.020 (2)	0.022 (2)	0.0140 (18)	−0.0022 (17)	0.0038 (16)	0.0004 (16)
C1	0.030 (2)	0.021 (2)	0.0133 (18)	0.004 (2)	0.0085 (17)	0.0038 (18)
C2	0.029 (2)	0.027 (3)	0.023 (2)	0.001 (2)	0.0129 (19)	0.0079 (19)
C3	0.022 (2)	0.024 (3)	0.027 (2)	−0.0013 (19)	0.0033 (19)	0.0067 (19)
C4	0.032 (3)	0.024 (3)	0.016 (2)	−0.002 (2)	0.0024 (18)	0.0014 (18)
C5	0.027 (2)	0.025 (3)	0.016 (2)	0.003 (2)	0.0082 (17)	0.0047 (18)
C6	0.026 (2)	0.014 (2)	0.0195 (19)	0.0019 (18)	0.0104 (17)	0.0034 (17)
C7	0.026 (2)	0.024 (2)	0.0122 (18)	0.006 (2)	0.0053 (16)	0.0012 (18)
C8	0.026 (2)	0.023 (2)	0.0130 (19)	0.0019 (19)	0.0060 (17)	0.0011 (17)
C9	0.023 (2)	0.024 (2)	0.0130 (19)	0.0029 (19)	0.0054 (17)	−0.0012 (17)
C10	0.023 (2)	0.020 (2)	0.0116 (18)	0.0030 (18)	0.0066 (16)	−0.0019 (16)
C11	0.021 (2)	0.023 (2)	0.0160 (19)	0.0023 (19)	0.0072 (16)	−0.0017 (18)
C12	0.026 (2)	0.023 (2)	0.0107 (18)	0.0020 (19)	0.0061 (17)	−0.0018 (17)
C13	0.023 (2)	0.015 (2)	0.0150 (19)	0.0039 (18)	0.0097 (16)	−0.0022 (16)
C14	0.021 (2)	0.019 (2)	0.0153 (19)	0.0000 (18)	0.0036 (16)	−0.0037 (17)
C15	0.025 (2)	0.023 (3)	0.0108 (18)	0.0059 (19)	0.0052 (16)	0.0012 (17)

Cl1—C1	1.749 (4)	C7—C8	1.325 (6)
O1—C9	1.226 (5)	C7—H7A	0.9300
N1—C13	1.374 (5)	C8—C9	1.491 (6)
N1—H1N1	0.84 (5)	C8—H8A	0.9300
N1—H2N1	0.83 (5)	C9—C10	1.471 (6)
C1—C2	1.389 (6)	C10—C15	1.386 (6)
C1—C6	1.400 (5)	C10—C11	1.408 (5)
C2—C3	1.387 (6)	C11—C12	1.376 (6)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.384 (6)	C12—C13	1.401 (6)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.375 (6)	C13—C14	1.405 (5)
C4—H4A	0.9300	C14—C15	1.375 (6)
C5—C6	1.404 (6)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.461 (6)
C13—N1—H1N1	116 (3)	C7—C8—C9	121.4 (4)
C13—N1—H2N1	111 (3)	C7—C8—H8A	119.3
H1N1—N1—H2N1	120 (4)	C9—C8—H8A	119.3
C2—C1—C6	122.7 (4)	O1—C9—C10	121.9 (4)
C2—C1—Cl1	116.8 (3)	O1—C9—C8	118.5 (4)
C6—C1—Cl1	120.6 (3)	C10—C9—C8	119.6 (3)
C3—C2—C1	119.2 (4)	C15—C10—C11	117.6 (4)
C3—C2—H2A	120.4	C15—C10—C9	119.3 (3)
C1—C2—H2A	120.4	C11—C10—C9	123.0 (4)
C4—C3—C2	119.5 (4)	C12—C11—C10	121.2 (4)
C4—C3—H3A	120.3	C12—C11—H11A	119.4
C2—C3—H3A	120.3	C10—C11—H11A	119.4
C5—C4—C3	120.7 (4)	C11—C12—C13	120.4 (4)
C5—C4—H4A	119.6	C11—C12—H12A	119.8
C3—C4—H4A	119.6	C13—C12—H12A	119.8
C4—C5—C6	121.7 (4)	N1—C13—C12	120.8 (4)
C4—C5—H5A	119.1	N1—C13—C14	120.4 (4)
C6—C5—H5A	119.1	C12—C13—C14	118.7 (4)
C1—C6—C5	116.1 (4)	C15—C14—C13	119.9 (4)
C1—C6—C7	122.2 (4)	C15—C14—H14A	120.0
C5—C6—C7	121.6 (4)	C13—C14—H14A	120.0
C8—C7—C6	126.0 (4)	C14—C15—C10	122.2 (4)
C8—C7—H7A	117.0	C14—C15—H15A	118.9
C6—C7—H7A	117.0	C10—C15—H15A	118.9
C6—C1—C2—C3	0.0 (7)	C7—C8—C9—C10	168.6 (4)
Cl1—C1—C2—C3	−178.4 (4)	O1—C9—C10—C15	−0.6 (6)
C1—C2—C3—C4	−0.7 (7)	C8—C9—C10—C15	179.9 (4)
C2—C3—C4—C5	0.7 (7)	O1—C9—C10—C11	−179.9 (4)
C3—C4—C5—C6	0.2 (7)	C8—C9—C10—C11	0.7 (6)
C2—C1—C6—C5	0.8 (6)	C15—C10—C11—C12	1.1 (6)
Cl1—C1—C6—C5	179.1 (3)	C9—C10—C11—C12	−179.6 (4)
C2—C1—C6—C7	178.7 (4)	C10—C11—C12—C13	−0.1 (6)
Cl1—C1—C6—C7	−3.0 (6)	C11—C12—C13—N1	−177.7 (4)
C4—C5—C6—C1	−0.9 (6)	C11—C12—C13—C14	−1.2 (6)
C4—C5—C6—C7	−178.8 (4)	N1—C13—C14—C15	178.0 (4)
C1—C6—C7—C8	163.8 (5)	C12—C13—C14—C15	1.5 (6)
C5—C6—C7—C8	−18.5 (7)	C13—C14—C15—C10	−0.5 (7)
C6—C7—C8—C9	179.9 (4)	C11—C10—C15—C14	−0.8 (6)
C7—C8—C9—O1	−10.9 (7)	C9—C10—C15—C14	179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N1i	0.85 (4)	2.30 (5)	3.098 (6)	158 (4)
N1—H2N1···O1ii	0.83 (4)	2.10 (4)	2.923 (5)	171 (4)
C7—H7A···Cl1	0.93	2.69	3.081 (5)	106.
C7—H7A···O1	0.93	2.45	2.775 (6)	101.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N1i	0.85 (4)	2.30 (5)	3.098 (6)	158 (4)
N1—H2N1⋯O1ii	0.83 (4)	2.10 (4)	2.923 (5)	171 (4)

Symmetry codes: (i) ; (ii) .