(2E)-3-[4-(Dimethyl­amino)phen­yl]-1-(3-nitro­phen­yl)prop-2-en-1-one

In the title compound, C₁₇H₁₆N₂O₃, the dihedral angle between the benzene rings is 1.56 (7)°. The nitro group is coplanar with the attached benzene ring while the dimethyl­amino group is twisted slightly away from the attached benzene ring. A weak intra­molecular C—H...O hydrogen bond is present in the mol­ecular structure. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds, forming chains along the [011] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.054
• wR factor = 0.162
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.822     0.996
            Tmin(prime) and Tmax expected:      0.945     0.996
            RR(prime) =      0.870
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Many chalcone derivatives crystallize as noncentrosymmetric structures and display significant non-linear optical (NLO) properties (Uchida et al., 1998; Patil et al., 2006; Shettigar et al., 2006). Crystals of the title compound, (I), do not exhibit second-order NLO properties, as the compound crystallizes in a centrosymmetric space group (Watson et al., 1993).

Bond lengths and angles in (I) (Fig. 1) have normal values (Allen et al., 1987). The dihedral angle between the benzene rings is 1.56 (7)°. The plane through the enone group (O1/C7—C9) makes dihedral angles of 10.47 (7) and 9.23 (7)°, respectively, with the C1—C6 and C10—C15 benzene rings. The nitro group attached at atom C2 is almost coplanar with the C1—C6 benzene ring, with torsion angles O2–N2–C2–C1 and O3–N2–C2–C3 of -2.5 (2)° and -2.1 (2)°, respectively. The dimethylamino group is twisted slightly away from the attached C10—C15 benzene ring, with torsion angles C16–N1–C13–C14 and C17–N1–C13–C12 of 10.5 (2)° and -8.3 (2)°, respectively.

An intramolecular C9—H9A···O1 interaction is observed in the molecular structure of (I), and it generates an S(5) ring motif (Bernstein et al., 1995). The molecules are linked into a chain along the [0 1 1] direction by intermolecular C17—H17C···O3ⁱ hydrogen bonds (Table 1). In addition, π-π interactions involving the C1—C6 (centroid Cg1) and C10—C15 (centroid Cg2) benzene rings is observed, with a Cg1···Cg2ⁱⁱ distance of 3.5164 (8) Å. Symmetry codes: (i) x,-1 + y,-1 + z; (ii) 1 - x, -y, 1 - z.

Related literature

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For general background and related literature, see: Uchida et al. (1998); Watson et al. (1993); Patil, Dharmaprakash et al. (2006); Shettigar et al. (2006).

S2. Experimental

N,N-dimethylaminobenzaldehyde (0.01 mol) and 3-nitroacetophenone (0.01 mol) were stirred in methanol (60 ml) at room temperature. 10% of NaOH aqueous solution (5 g) was added and the mixture was stirred for 2 h. The resulting precipitate was filtered off, washed with water and dried. The resulting crude product recrystallized from acetone. Crystals of (I) suitable for X-ray analysis were grown by slow evaporation of an acetone solution at room temperature.

S3. Refinement

All H atoms were refined using a riding model, with C—H distances in the range 0.93–0.96 Å. The U_iso(H) values were constrained to be 1.5U_eq of the carrier atom for methyl H and 1.2U_eq for the remaining H atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); 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).

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

(2E)-3-[4-(dimethylamino)phenyl]-1-(3-nitrophenyl) prop-2-en-1-one

Crystal data

C17H16N2O3	Z = 2
Mr = 296.32	F(000) = 312
Triclinic, P1	Dx = 1.377 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4326 (2) Å	Cell parameters from 2515 reflections
b = 7.1724 (2) Å	θ = 3.0–30.0°
c = 16.5000 (6) Å	µ = 0.10 mm^−1
α = 93.989 (2)°	T = 100 K
β = 96.973 (2)°	Plate, red
γ = 107.844 (2)°	0.58 × 0.25 × 0.04 mm
V = 714.68 (4) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4139 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.3°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.822, Tmax = 0.996	l = −23→22
12950 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0746P)^2 + 0.1229P] where P = (Fo^2 + 2Fc^2)/3
4139 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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

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
O1	0.20474 (19)	0.31302 (18)	0.58398 (7)	0.0307 (3)
O2	0.4006 (2)	0.58466 (19)	0.86676 (8)	0.0358 (3)
O3	0.7425 (2)	0.7068 (2)	0.92259 (7)	0.0403 (3)
N1	0.3580 (2)	−0.16780 (19)	0.12184 (8)	0.0242 (3)
N2	0.5992 (2)	0.6233 (2)	0.86426 (8)	0.0268 (3)
C1	0.5108 (3)	0.4710 (2)	0.72163 (9)	0.0208 (3)
H1A	0.3618	0.4382	0.7267	0.025*
C2	0.6705 (3)	0.5694 (2)	0.78695 (9)	0.0214 (3)
C3	0.8939 (3)	0.6208 (2)	0.78275 (10)	0.0240 (3)
H3A	0.9984	0.6875	0.8278	0.029*
C4	0.9570 (3)	0.5698 (2)	0.70954 (10)	0.0241 (3)
H4A	1.1064	0.6022	0.7051	0.029*
C5	0.8002 (3)	0.4708 (2)	0.64249 (10)	0.0219 (3)
H5A	0.8458	0.4373	0.5937	0.026*
C6	0.5761 (2)	0.4212 (2)	0.64736 (9)	0.0193 (3)
C7	0.3950 (3)	0.3212 (2)	0.57715 (9)	0.0210 (3)
C8	0.4516 (3)	0.2383 (2)	0.50196 (9)	0.0214 (3)
H8A	0.5986	0.2544	0.4973	0.026*
C9	0.2920 (3)	0.1398 (2)	0.44018 (9)	0.0215 (3)
H9A	0.1479	0.1214	0.4497	0.026*
C10	0.3166 (3)	0.0582 (2)	0.36015 (9)	0.0199 (3)
C11	0.5214 (3)	0.0810 (2)	0.33381 (9)	0.0211 (3)
H11A	0.6505	0.1461	0.3699	0.025*
C12	0.5359 (3)	0.0091 (2)	0.25577 (9)	0.0214 (3)
H12A	0.6743	0.0273	0.2401	0.026*
C13	0.3440 (3)	−0.0919 (2)	0.19893 (9)	0.0205 (3)
C14	0.1394 (3)	−0.1144 (2)	0.22557 (9)	0.0228 (3)
H14A	0.0099	−0.1794	0.1898	0.027*
C15	0.1271 (3)	−0.0417 (2)	0.30389 (9)	0.0222 (3)
H15A	−0.0110	−0.0596	0.3197	0.027*
C16	0.1605 (3)	−0.2440 (3)	0.06120 (10)	0.0302 (4)
H16A	0.0543	−0.3489	0.0816	0.045*
H16B	0.1976	−0.2932	0.0112	0.045*
H16C	0.0988	−0.1404	0.0507	0.045*
C17	0.5695 (3)	−0.1231 (3)	0.09321 (11)	0.0336 (4)
H17A	0.6665	−0.1716	0.1284	0.050*
H17B	0.6326	0.0170	0.0941	0.050*
H17C	0.5499	−0.1850	0.0381	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0225 (6)	0.0426 (7)	0.0256 (6)	0.0097 (5)	0.0054 (5)	−0.0044 (5)
O2	0.0301 (7)	0.0514 (8)	0.0276 (7)	0.0160 (6)	0.0078 (5)	−0.0043 (5)
O3	0.0400 (8)	0.0535 (8)	0.0233 (7)	0.0158 (6)	−0.0023 (6)	−0.0142 (6)
N1	0.0239 (7)	0.0293 (7)	0.0180 (7)	0.0086 (5)	0.0007 (5)	−0.0030 (5)
N2	0.0304 (8)	0.0307 (7)	0.0209 (7)	0.0136 (6)	0.0032 (6)	−0.0023 (5)
C1	0.0224 (8)	0.0197 (7)	0.0220 (8)	0.0091 (6)	0.0042 (6)	0.0016 (5)
C2	0.0273 (8)	0.0209 (7)	0.0188 (7)	0.0115 (6)	0.0056 (6)	0.0005 (5)
C3	0.0259 (8)	0.0201 (7)	0.0241 (8)	0.0069 (6)	−0.0009 (6)	−0.0006 (6)
C4	0.0198 (8)	0.0220 (7)	0.0305 (9)	0.0068 (6)	0.0047 (6)	0.0018 (6)
C5	0.0246 (8)	0.0205 (7)	0.0233 (8)	0.0097 (6)	0.0077 (6)	0.0025 (6)
C6	0.0231 (8)	0.0161 (6)	0.0199 (7)	0.0076 (6)	0.0044 (6)	0.0026 (5)
C7	0.0238 (8)	0.0200 (7)	0.0197 (7)	0.0072 (6)	0.0055 (6)	0.0013 (5)
C8	0.0228 (8)	0.0221 (7)	0.0206 (8)	0.0087 (6)	0.0049 (6)	0.0006 (5)
C9	0.0248 (8)	0.0200 (7)	0.0217 (8)	0.0090 (6)	0.0059 (6)	0.0029 (6)
C10	0.0249 (8)	0.0167 (6)	0.0186 (7)	0.0076 (6)	0.0027 (6)	0.0015 (5)
C11	0.0220 (8)	0.0196 (7)	0.0198 (7)	0.0058 (6)	0.0000 (6)	−0.0006 (5)
C12	0.0209 (7)	0.0221 (7)	0.0212 (8)	0.0071 (6)	0.0035 (6)	0.0004 (6)
C13	0.0260 (8)	0.0172 (6)	0.0185 (7)	0.0082 (6)	0.0019 (6)	0.0000 (5)
C14	0.0228 (8)	0.0211 (7)	0.0221 (8)	0.0060 (6)	−0.0016 (6)	−0.0009 (6)
C15	0.0220 (8)	0.0225 (7)	0.0230 (8)	0.0081 (6)	0.0039 (6)	0.0027 (6)
C16	0.0315 (9)	0.0332 (9)	0.0209 (8)	0.0065 (7)	−0.0012 (7)	−0.0037 (6)
C17	0.0308 (9)	0.0447 (10)	0.0243 (9)	0.0125 (8)	0.0054 (7)	−0.0061 (7)

Geometric parameters (Å, º)

O1—C7	1.2268 (18)	C8—H8A	0.93
O2—N2	1.2282 (18)	C9—C10	1.453 (2)
O3—N2	1.2253 (18)	C9—H9A	0.93
N1—C13	1.3726 (19)	C10—C15	1.400 (2)
N1—C17	1.445 (2)	C10—C11	1.403 (2)
N1—C16	1.450 (2)	C11—C12	1.378 (2)
N2—C2	1.4728 (19)	C11—H11A	0.93
C1—C2	1.377 (2)	C12—C13	1.416 (2)
C1—C6	1.401 (2)	C12—H12A	0.93
C1—H1A	0.93	C13—C14	1.404 (2)
C2—C3	1.382 (2)	C14—C15	1.380 (2)
C3—C4	1.380 (2)	C14—H14A	0.93
C3—H3A	0.93	C15—H15A	0.93
C4—C5	1.388 (2)	C16—H16A	0.96
C4—H4A	0.93	C16—H16B	0.96
C5—C6	1.389 (2)	C16—H16C	0.96
C5—H5A	0.93	C17—H17A	0.96
C6—C7	1.503 (2)	C17—H17B	0.96
C7—C8	1.471 (2)	C17—H17C	0.96
C8—C9	1.339 (2)
C13—N1—C17	120.03 (13)	C10—C9—H9A	116.0
C13—N1—C16	119.75 (13)	C15—C10—C11	117.16 (13)
C17—N1—C16	117.94 (13)	C15—C10—C9	119.05 (14)
O3—N2—O2	123.47 (14)	C11—C10—C9	123.73 (14)
O3—N2—C2	117.85 (14)	C12—C11—C10	121.55 (14)
O2—N2—C2	118.67 (13)	C12—C11—H11A	119.2
C2—C1—C6	118.98 (14)	C10—C11—H11A	119.2
C2—C1—H1A	120.5	C11—C12—C13	121.21 (14)
C6—C1—H1A	120.5	C11—C12—H12A	119.4
C1—C2—C3	122.83 (14)	C13—C12—H12A	119.4
C1—C2—N2	118.35 (14)	N1—C13—C14	121.62 (14)
C3—C2—N2	118.82 (14)	N1—C13—C12	121.33 (14)
C4—C3—C2	117.84 (15)	C14—C13—C12	117.04 (13)
C4—C3—H3A	121.1	C15—C14—C13	121.22 (14)
C2—C3—H3A	121.1	C15—C14—H14A	119.4
C3—C4—C5	120.78 (15)	C13—C14—H14A	119.4
C3—C4—H4A	119.6	C14—C15—C10	121.82 (14)
C5—C4—H4A	119.6	C14—C15—H15A	119.1
C4—C5—C6	120.80 (14)	C10—C15—H15A	119.1
C4—C5—H5A	119.6	N1—C16—H16A	109.5
C6—C5—H5A	119.6	N1—C16—H16B	109.5
C5—C6—C1	118.76 (14)	H16A—C16—H16B	109.5
C5—C6—C7	124.49 (13)	N1—C16—H16C	109.5
C1—C6—C7	116.73 (13)	H16A—C16—H16C	109.5
O1—C7—C8	122.01 (14)	H16B—C16—H16C	109.5
O1—C7—C6	118.94 (13)	N1—C17—H17A	109.5
C8—C7—C6	119.04 (13)	N1—C17—H17B	109.5
C9—C8—C7	120.16 (14)	H17A—C17—H17B	109.5
C9—C8—H8A	119.9	N1—C17—H17C	109.5
C7—C8—H8A	119.9	H17A—C17—H17C	109.5
C8—C9—C10	127.92 (15)	H17B—C17—H17C	109.5
C8—C9—H9A	116.0
C6—C1—C2—C3	−0.4 (2)	C6—C7—C8—C9	176.63 (13)
C6—C1—C2—N2	179.16 (12)	C7—C8—C9—C10	176.15 (14)
O3—N2—C2—C1	178.37 (14)	C8—C9—C10—C15	179.55 (14)
O2—N2—C2—C1	−2.5 (2)	C8—C9—C10—C11	−3.4 (2)
O3—N2—C2—C3	−2.1 (2)	C15—C10—C11—C12	0.3 (2)
O2—N2—C2—C3	177.06 (14)	C9—C10—C11—C12	−176.72 (14)
C1—C2—C3—C4	−0.1 (2)	C10—C11—C12—C13	−0.3 (2)
N2—C2—C3—C4	−179.64 (13)	C17—N1—C13—C14	173.04 (14)
C2—C3—C4—C5	0.2 (2)	C16—N1—C13—C14	10.5 (2)
C3—C4—C5—C6	0.2 (2)	C17—N1—C13—C12	−8.3 (2)
C4—C5—C6—C1	−0.7 (2)	C16—N1—C13—C12	−170.82 (13)
C4—C5—C6—C7	177.56 (13)	C11—C12—C13—N1	−178.40 (13)
C2—C1—C6—C5	0.7 (2)	C11—C12—C13—C14	0.3 (2)
C2—C1—C6—C7	−177.63 (12)	N1—C13—C14—C15	178.41 (13)
C5—C6—C7—O1	−168.19 (14)	C12—C13—C14—C15	−0.3 (2)
C1—C6—C7—O1	10.1 (2)	C13—C14—C15—C10	0.3 (2)
C5—C6—C7—C8	11.0 (2)	C11—C10—C15—C14	−0.3 (2)
C1—C6—C7—C8	−170.71 (12)	C9—C10—C15—C14	176.88 (13)
O1—C7—C8—C9	−4.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.45	2.798 (2)	102
C17—H17C···O3^i	0.96	2.59	3.430 (2)	146

Symmetry code: (i) x, y−1, z−1.