(2E)-1-(4-Chloro-phen-yl)-3-(4-nitro-phen-yl)prop-2-en-1-one.

In the title compound, C15H10ClNO3, a substituted chalcone, the dihedral angle between the benzene rings is 5.1 (7)°. The nitro group makes a dihedral angle of 12.5 (3)° with the benzene ring to which it is attached. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into a one-dimensional array along [010]. The crystal studied was an inversion twin, with a refined ratio for the twin components of 0.6060 (9):0.3939 (1).

Related literature

For the biochemical activity of chalcones, see: Dimmock et al. (1999 ▶). For different chalcone derivatives, see: Samshuddin et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010a ▶,b ▶); Baktır et al. (2011a ▶,b ▶). For related structures, see: Jing (2009 ▶); Jasinski et al. (2008 ▶, 2010a ▶,b ▶); Fun et al. (2011 ▶); Sarojini et al. (2007 ▶); Ma (2007 ▶).

Experimental

Crystal data

C15H10ClNO3

M = 287.69

Orthorhombic,

a = 42.9266 (17) Å

b = 5.9741 (3) Å

c = 5.0680 (2) Å

V = 1299.68 (10) Å3

Z = 4

Cu Kα radiation

μ = 2.67 mm−1

T = 173 K

0.42 × 0.08 × 0.04 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.803, T max = 1.000

12814 measured reflections

2538 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.100

S = 1.14

2538 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010854/fj2627sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010854/fj2627Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010854/fj2627Isup3.cml

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

C15H10ClNO3	Dx = 1.470 Mg m−3
Mr = 287.69	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pna21	Cell parameters from 5168 reflections
a = 42.9266 (17) Å	θ = 3.3–32.2°
b = 5.9741 (3) Å	µ = 2.67 mm−1
c = 5.0680 (2) Å	T = 173 K
V = 1299.68 (10) Å3	Rod, colorless
Z = 4	0.42 × 0.08 × 0.04 mm
F(000) = 592

Agilent Xcalibur (Eos, Gemini) diffractometer	2481 reflections with I > 2σ(I)
Detector resolution: 16.1500 pixels mm-1	Rint = 0.037
ω scans	θmax = 89.4°, θmin = 7.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −55→55
Tmin = 0.803, Tmax = 1.000	k = −7→7
12814 measured reflections	l = −4→6
2538 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0202P)2 + 1.4764P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.22 e Å−3
2538 reflections	Δρmin = −0.39 e Å−3
182 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Flack parameter: 0.39 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq
Cl1	0.25813 (2)	−0.1905 (2)	1.5999 (3)	0.0500 (3)
O1	0.36902 (7)	−0.7676 (5)	0.9840 (8)	0.0475 (9)
O2	0.49287 (6)	−0.1656 (4)	−0.2914 (6)	0.0318 (6)
O3	0.46280 (6)	0.1223 (4)	−0.2523 (6)	0.0325 (6)
N1	0.47115 (6)	−0.0656 (5)	−0.1880 (6)	0.0233 (6)
C1	0.36318 (8)	−0.5698 (6)	0.9597 (9)	0.0275 (8)
C2	0.33781 (7)	−0.4654 (6)	1.1220 (9)	0.0263 (7)
C3	0.32630 (8)	−0.2524 (6)	1.0729 (9)	0.0326 (9)
H3	0.3351	−0.1653	0.9406	0.039*
C4	0.30164 (9)	−0.1685 (7)	1.2203 (9)	0.0359 (9)
H4	0.2936	−0.0270	1.1850	0.043*
C5	0.28918 (8)	−0.2975 (7)	1.4195 (9)	0.0317 (9)
C6	0.30051 (9)	−0.5094 (7)	1.4746 (9)	0.0340 (9)
H6	0.2918	−0.5950	1.6091	0.041*
C7	0.32480 (8)	−0.5907 (7)	1.3268 (9)	0.0311 (9)
H7	0.3328	−0.7320	1.3639	0.037*
C8	0.38006 (8)	−0.4296 (6)	0.7654 (8)	0.0263 (8)
H8	0.3743	−0.2807	0.7436	0.032*
C9	0.40321 (7)	−0.5122 (6)	0.6217 (9)	0.0258 (7)
H9	0.4088	−0.6602	0.6527	0.031*
C10	0.42078 (7)	−0.3904 (5)	0.4177 (7)	0.0204 (7)
C11	0.44691 (8)	−0.4917 (5)	0.3052 (8)	0.0238 (7)
H11	0.4531	−0.6323	0.3636	0.029*
C12	0.46373 (7)	−0.3858 (5)	0.1074 (8)	0.0220 (7)
H12	0.4811	−0.4538	0.0320	0.026*
C13	0.45406 (7)	−0.1771 (5)	0.0260 (7)	0.0188 (7)
C14	0.42835 (7)	−0.0721 (5)	0.1327 (8)	0.0242 (7)
H14	0.4223	0.0688	0.0737	0.029*
C15	0.41184 (8)	−0.1789 (6)	0.3268 (8)	0.0261 (8)
H15	0.3944	−0.1097	0.3993	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.0414 (5)	0.0599 (7)	0.0487 (6)	0.0036 (5)	0.0136 (5)	−0.0095 (7)
O1	0.0412 (15)	0.0303 (14)	0.071 (2)	0.0065 (12)	0.0231 (16)	0.0156 (16)
O2	0.0357 (14)	0.0297 (13)	0.0301 (15)	0.0025 (10)	0.0093 (12)	0.0015 (12)
O3	0.0381 (14)	0.0251 (13)	0.0343 (16)	0.0044 (10)	0.0002 (12)	0.0136 (13)
N1	0.0264 (14)	0.0223 (13)	0.0213 (16)	−0.0014 (11)	−0.0021 (12)	0.0037 (12)
C1	0.0201 (16)	0.0260 (17)	0.036 (2)	−0.0017 (13)	−0.0007 (15)	0.0055 (17)
C2	0.0204 (14)	0.0298 (18)	0.0286 (19)	−0.0037 (12)	−0.0013 (16)	0.0020 (18)
C3	0.0343 (18)	0.032 (2)	0.031 (2)	−0.0026 (15)	0.0078 (18)	0.0044 (19)
C4	0.0338 (19)	0.0298 (18)	0.044 (3)	0.0037 (15)	0.0088 (19)	−0.0001 (19)
C5	0.0233 (16)	0.039 (2)	0.033 (2)	−0.0030 (15)	−0.0001 (16)	−0.0133 (18)
C6	0.0293 (18)	0.043 (2)	0.029 (2)	−0.0116 (17)	0.0002 (17)	0.005 (2)
C7	0.0252 (17)	0.0332 (19)	0.035 (2)	−0.0038 (14)	−0.0031 (16)	0.0070 (18)
C8	0.0228 (16)	0.0266 (17)	0.029 (2)	−0.0004 (13)	0.0001 (15)	0.0043 (17)
C9	0.0240 (15)	0.0263 (16)	0.0271 (19)	−0.0012 (13)	−0.0001 (16)	0.0059 (18)
C10	0.0188 (14)	0.0201 (15)	0.0223 (18)	−0.0006 (12)	−0.0033 (13)	0.0003 (14)
C11	0.0261 (16)	0.0184 (15)	0.027 (2)	0.0011 (12)	−0.0018 (14)	0.0059 (16)
C12	0.0220 (14)	0.0189 (14)	0.0252 (18)	0.0030 (12)	−0.0021 (15)	−0.0006 (16)
C13	0.0206 (14)	0.0187 (14)	0.0172 (17)	−0.0016 (12)	−0.0021 (12)	0.0017 (13)
C14	0.0256 (15)	0.0188 (15)	0.028 (2)	0.0034 (12)	−0.0015 (15)	0.0053 (16)
C15	0.0228 (16)	0.0236 (16)	0.032 (2)	0.0053 (13)	0.0019 (15)	−0.0025 (17)

Cl1—C5	1.738 (4)	C7—H7	0.9300
O1—C1	1.214 (4)	C8—C9	1.327 (5)
O2—N1	1.225 (4)	C8—H8	0.9300
O3—N1	1.222 (4)	C9—C10	1.472 (5)
N1—C13	1.469 (4)	C9—H9	0.9300
C1—C8	1.482 (5)	C10—C11	1.397 (5)
C1—C2	1.501 (5)	C10—C15	1.398 (5)
C2—C3	1.388 (5)	C11—C12	1.388 (5)
C2—C7	1.396 (5)	C11—H11	0.9300
C3—C4	1.389 (5)	C12—C13	1.377 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (6)	C13—C14	1.380 (4)
C4—H4	0.9300	C14—C15	1.370 (5)
C5—C6	1.384 (6)	C14—H14	0.9300
C6—C7	1.372 (6)	C15—H15	0.9300
C6—H6	0.9300
O3—N1—O2	123.8 (3)	C9—C8—C1	121.4 (3)
O3—N1—C13	117.8 (3)	C9—C8—H8	119.3
O2—N1—C13	118.3 (3)	C1—C8—H8	119.3
O1—C1—C8	121.1 (4)	C8—C9—C10	125.8 (3)
O1—C1—C2	119.9 (3)	C8—C9—H9	117.1
C8—C1—C2	119.0 (3)	C10—C9—H9	117.1
C3—C2—C7	118.9 (4)	C11—C10—C15	118.5 (3)
C3—C2—C1	122.7 (4)	C11—C10—C9	119.0 (3)
C7—C2—C1	118.4 (3)	C15—C10—C9	122.5 (3)
C2—C3—C4	120.4 (4)	C12—C11—C10	121.0 (3)
C2—C3—H3	119.8	C12—C11—H11	119.5
C4—C3—H3	119.8	C10—C11—H11	119.5
C5—C4—C3	119.2 (4)	C13—C12—C11	118.2 (3)
C5—C4—H4	120.4	C13—C12—H12	120.9
C3—C4—H4	120.4	C11—C12—H12	120.9
C4—C5—C6	121.5 (4)	C12—C13—C14	122.4 (3)
C4—C5—Cl1	118.5 (3)	C12—C13—N1	118.8 (3)
C6—C5—Cl1	120.0 (3)	C14—C13—N1	118.9 (3)
C7—C6—C5	118.7 (4)	C15—C14—C13	118.9 (3)
C7—C6—H6	120.6	C15—C14—H14	120.5
C5—C6—H6	120.6	C13—C14—H14	120.5
C6—C7—C2	121.3 (4)	C14—C15—C10	121.0 (3)
C6—C7—H7	119.3	C14—C15—H15	119.5
C2—C7—H7	119.3	C10—C15—H15	119.5
O1—C1—C2—C3	−168.6 (4)	C8—C9—C10—C11	172.5 (4)
C8—C1—C2—C3	9.6 (6)	C8—C9—C10—C15	−9.2 (6)
O1—C1—C2—C7	9.9 (6)	C15—C10—C11—C12	0.0 (5)
C8—C1—C2—C7	−172.0 (3)	C9—C10—C11—C12	178.3 (3)
C7—C2—C3—C4	−1.9 (6)	C10—C11—C12—C13	0.4 (5)
C1—C2—C3—C4	176.5 (4)	C11—C12—C13—C14	−0.4 (5)
C2—C3—C4—C5	1.4 (7)	C11—C12—C13—N1	−178.4 (3)
C3—C4—C5—C6	−0.5 (6)	O3—N1—C13—C12	−177.9 (3)
C3—C4—C5—Cl1	−179.5 (3)	O2—N1—C13—C12	2.1 (5)
C4—C5—C6—C7	0.3 (6)	O3—N1—C13—C14	4.1 (5)
Cl1—C5—C6—C7	179.2 (3)	O2—N1—C13—C14	−176.0 (3)
C5—C6—C7—C2	−0.9 (6)	C12—C13—C14—C15	0.1 (5)
C3—C2—C7—C6	1.7 (6)	N1—C13—C14—C15	178.1 (3)
C1—C2—C7—C6	−176.8 (4)	C13—C14—C15—C10	0.3 (6)
O1—C1—C8—C9	−3.7 (6)	C11—C10—C15—C14	−0.3 (5)
C2—C1—C8—C9	178.3 (4)	C9—C10—C15—C14	−178.6 (4)
C1—C8—C9—C10	177.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.69	3.304 (4)	125
C14—H14···O1ii	0.93	2.53	3.219 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.69	3.304 (4)	125
C14—H14⋯O1ii	0.93	2.53	3.219 (4)	131

Symmetry codes: (i) ; (ii) .