(2E)-3-(3-Nitro-phen-yl)-1-[4-(piperidin-1-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(20)H(20)N(2)O(3), the piperidine ring adopts a chair conformation and its mean plane forms dihedral angles of 19.63 (9) and 19.44 (9)°, respectively, with the benzene and the nitro-substituted benzene ring. The benzene and nitro-substituted benzene rings are almost coplanar and make a dihedral angle of 4.78 (8)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into two-dimensional networks parallel to the ab plane. The crystal packing is further stabilized by π-π inter-actions [maximum centroid-centroid distance = 3.7807 (12) Å].

Related literature

For related structures and background to chalcones, see: Fun et al. (2011a ▶,b ▶,c ▶,d ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H20N2O3

M = 336.38

Orthorhombic,

a = 7.4268 (12) Å

b = 11.3884 (18) Å

c = 39.447 (6) Å

V = 3336.4 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.22 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.973, T max = 0.990

20847 measured reflections

4870 independent reflections

3174 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.154

S = 1.04

4870 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008847/ds2176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008847/ds2176Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008847/ds2176Isup3.cml

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

C20H20N2O3	F(000) = 1424
Mr = 336.38	Dx = 1.339 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2665 reflections
a = 7.4268 (12) Å	θ = 3.1–29.6°
b = 11.3884 (18) Å	µ = 0.09 mm−1
c = 39.447 (6) Å	T = 100 K
V = 3336.4 (9) Å3	Block, orange
Z = 8	0.30 × 0.22 × 0.11 mm

Bruker APEX DUO CCD area-detector diffractometer	4870 independent reflections
Radiation source: fine-focus sealed tube	3174 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 30.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.973, Tmax = 0.990	k = −16→16
20847 measured reflections	l = −55→47

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0603P)2 + 1.4691P] where P = (Fo2 + 2Fc2)/3
4870 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.6504 (2)	0.26696 (11)	−0.01933 (3)	0.0378 (4)
O2	0.9010 (2)	0.54808 (13)	0.17630 (4)	0.0448 (4)
O3	0.8344 (2)	0.37615 (12)	0.15668 (3)	0.0388 (4)
N1	0.5842 (2)	0.49503 (12)	−0.16639 (4)	0.0282 (4)
N2	0.8685 (2)	0.48100 (13)	0.15277 (4)	0.0297 (4)
C1	0.6185 (3)	0.40300 (17)	−0.19185 (5)	0.0370 (5)
H1A	0.5738	0.3285	−0.1834	0.044*
H1B	0.7473	0.3954	−0.1953	0.044*
C2	0.5292 (3)	0.43002 (18)	−0.22548 (5)	0.0403 (5)
H2A	0.5638	0.3710	−0.2420	0.048*
H2B	0.3995	0.4266	−0.2228	0.048*
C3	0.5819 (3)	0.55016 (19)	−0.23851 (5)	0.0372 (5)
H3A	0.5138	0.5681	−0.2588	0.045*
H3B	0.7089	0.5507	−0.2443	0.045*
C4	0.5445 (3)	0.64214 (17)	−0.21165 (5)	0.0352 (5)
H4A	0.4157	0.6478	−0.2080	0.042*
H4B	0.5870	0.7179	−0.2195	0.042*
C5	0.6370 (3)	0.61159 (16)	−0.17848 (5)	0.0333 (5)
H5A	0.7664	0.6138	−0.1817	0.040*
H5B	0.6059	0.6698	−0.1615	0.040*
C6	0.6084 (2)	0.46749 (14)	−0.13234 (4)	0.0234 (4)
C7	0.5554 (3)	0.35640 (14)	−0.11964 (5)	0.0260 (4)
H7A	0.5074	0.3008	−0.1344	0.031*
C8	0.5738 (3)	0.32971 (14)	−0.08587 (4)	0.0242 (4)
H8A	0.5381	0.2560	−0.0783	0.029*
C9	0.6450 (2)	0.41027 (13)	−0.06242 (4)	0.0215 (4)
C10	0.6947 (2)	0.52043 (13)	−0.07476 (4)	0.0211 (3)
H10A	0.7399	0.5763	−0.0598	0.025*
C11	0.6784 (2)	0.54852 (14)	−0.10881 (4)	0.0229 (4)
H11A	0.7144	0.6223	−0.1163	0.027*
C12	0.6717 (3)	0.37118 (14)	−0.02707 (4)	0.0249 (4)
C13	0.7283 (3)	0.45833 (14)	−0.00107 (4)	0.0241 (4)
H13A	0.7355	0.5375	−0.0067	0.029*
C14	0.7688 (3)	0.42367 (14)	0.03032 (4)	0.0243 (4)
H14A	0.7605	0.3437	0.0348	0.029*
C15	0.8250 (2)	0.49959 (13)	0.05843 (4)	0.0213 (3)
C16	0.8867 (2)	0.61466 (14)	0.05323 (5)	0.0236 (4)
H16A	0.8917	0.6449	0.0313	0.028*
C17	0.9403 (3)	0.68375 (14)	0.08030 (5)	0.0272 (4)
H17A	0.9826	0.7594	0.0763	0.033*
C18	0.9318 (3)	0.64173 (14)	0.11314 (5)	0.0266 (4)
H18A	0.9652	0.6887	0.1314	0.032*
C19	0.8721 (2)	0.52768 (15)	0.11814 (4)	0.0236 (4)
C20	0.8195 (2)	0.45610 (14)	0.09165 (4)	0.0221 (4)
H20A	0.7809	0.3798	0.0958	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0575 (11)	0.0194 (6)	0.0366 (7)	−0.0105 (6)	−0.0024 (7)	−0.0006 (5)
O2	0.0530 (11)	0.0507 (9)	0.0308 (7)	−0.0046 (8)	−0.0067 (7)	−0.0089 (6)
O3	0.0516 (10)	0.0305 (7)	0.0342 (7)	0.0097 (7)	0.0058 (7)	0.0024 (6)
N1	0.0357 (10)	0.0217 (7)	0.0273 (7)	0.0073 (7)	−0.0075 (7)	−0.0091 (6)
N2	0.0293 (9)	0.0296 (8)	0.0301 (8)	0.0053 (7)	−0.0011 (7)	−0.0036 (6)
C1	0.0449 (14)	0.0328 (10)	0.0334 (10)	0.0072 (9)	−0.0069 (9)	−0.0158 (8)
C2	0.0478 (15)	0.0418 (11)	0.0312 (10)	0.0023 (10)	−0.0072 (9)	−0.0146 (8)
C3	0.0303 (12)	0.0533 (13)	0.0280 (9)	−0.0016 (10)	−0.0009 (8)	−0.0081 (9)
C4	0.0414 (13)	0.0365 (10)	0.0279 (9)	0.0028 (9)	−0.0026 (9)	0.0000 (8)
C5	0.0452 (14)	0.0261 (9)	0.0287 (9)	0.0047 (9)	−0.0062 (9)	−0.0064 (7)
C6	0.0218 (9)	0.0198 (7)	0.0287 (8)	0.0071 (7)	−0.0053 (7)	−0.0067 (6)
C7	0.0234 (10)	0.0200 (8)	0.0346 (9)	0.0018 (7)	−0.0059 (7)	−0.0100 (7)
C8	0.0208 (10)	0.0158 (7)	0.0361 (9)	−0.0002 (6)	−0.0011 (7)	−0.0049 (6)
C9	0.0181 (9)	0.0161 (7)	0.0303 (8)	0.0012 (6)	0.0001 (7)	−0.0048 (6)
C10	0.0195 (9)	0.0148 (7)	0.0290 (8)	0.0010 (6)	−0.0017 (7)	−0.0060 (6)
C11	0.0232 (10)	0.0159 (7)	0.0295 (8)	0.0028 (7)	−0.0013 (7)	−0.0048 (6)
C12	0.0247 (10)	0.0200 (7)	0.0300 (9)	−0.0017 (7)	0.0005 (7)	−0.0037 (6)
C13	0.0262 (10)	0.0167 (7)	0.0295 (9)	0.0003 (7)	0.0000 (7)	−0.0030 (6)
C14	0.0260 (10)	0.0159 (7)	0.0309 (9)	−0.0017 (7)	0.0006 (7)	−0.0014 (6)
C15	0.0180 (9)	0.0150 (7)	0.0307 (8)	0.0012 (6)	−0.0007 (7)	−0.0024 (6)
C16	0.0202 (9)	0.0169 (7)	0.0337 (9)	0.0009 (7)	0.0007 (7)	−0.0002 (6)
C17	0.0224 (10)	0.0157 (7)	0.0435 (10)	−0.0008 (7)	−0.0006 (8)	−0.0043 (7)
C18	0.0210 (10)	0.0215 (8)	0.0373 (10)	0.0008 (7)	−0.0036 (7)	−0.0095 (7)
C19	0.0189 (9)	0.0234 (8)	0.0285 (8)	0.0052 (7)	−0.0011 (7)	−0.0028 (6)
C20	0.0209 (9)	0.0163 (7)	0.0291 (8)	0.0022 (6)	−0.0007 (7)	−0.0017 (6)

O1—C12	1.236 (2)	C7—H7A	0.9300
O2—N2	1.226 (2)	C8—C9	1.406 (2)
O3—N2	1.230 (2)	C8—H8A	0.9300
N1—C6	1.391 (2)	C9—C10	1.395 (2)
N1—C5	1.464 (2)	C9—C12	1.477 (2)
N1—C1	1.474 (2)	C10—C11	1.386 (2)
N2—C19	1.466 (2)	C10—H10A	0.9300
C1—C2	1.515 (3)	C11—H11A	0.9300
C1—H1A	0.9700	C12—C13	1.488 (2)
C1—H1B	0.9700	C13—C14	1.334 (2)
C2—C3	1.513 (3)	C13—H13A	0.9300
C2—H2A	0.9700	C14—C15	1.467 (2)
C2—H2B	0.9700	C14—H14A	0.9300
C3—C4	1.516 (3)	C15—C20	1.401 (2)
C3—H3A	0.9700	C15—C16	1.403 (2)
C3—H3B	0.9700	C16—C17	1.385 (2)
C4—C5	1.518 (3)	C16—H16A	0.9300
C4—H4A	0.9700	C17—C18	1.382 (3)
C4—H4B	0.9700	C17—H17A	0.9300
C5—H5A	0.9700	C18—C19	1.387 (2)
C5—H5B	0.9700	C18—H18A	0.9300
C6—C11	1.408 (2)	C19—C20	1.382 (2)
C6—C7	1.417 (2)	C20—H20A	0.9300
C7—C8	1.373 (2)
C6—N1—C5	118.97 (14)	C6—C7—H7A	119.6
C6—N1—C1	118.37 (14)	C7—C8—C9	122.09 (16)
C5—N1—C1	112.13 (15)	C7—C8—H8A	119.0
O2—N2—O3	123.40 (16)	C9—C8—H8A	119.0
O2—N2—C19	118.41 (15)	C10—C9—C8	117.18 (16)
O3—N2—C19	118.19 (14)	C10—C9—C12	124.39 (15)
N1—C1—C2	112.11 (16)	C8—C9—C12	118.34 (15)
N1—C1—H1A	109.2	C11—C10—C9	121.49 (15)
C2—C1—H1A	109.2	C11—C10—H10A	119.3
N1—C1—H1B	109.2	C9—C10—H10A	119.3
C2—C1—H1B	109.2	C10—C11—C6	121.31 (15)
H1A—C1—H1B	107.9	C10—C11—H11A	119.3
C3—C2—C1	111.60 (18)	C6—C11—H11A	119.3
C3—C2—H2A	109.3	O1—C12—C9	120.37 (15)
C1—C2—H2A	109.3	O1—C12—C13	120.44 (16)
C3—C2—H2B	109.3	C9—C12—C13	119.18 (14)
C1—C2—H2B	109.3	C14—C13—C12	120.41 (15)
H2A—C2—H2B	108.0	C14—C13—H13A	119.8
C2—C3—C4	109.88 (17)	C12—C13—H13A	119.8
C2—C3—H3A	109.7	C13—C14—C15	126.26 (15)
C4—C3—H3A	109.7	C13—C14—H14A	116.9
C2—C3—H3B	109.7	C15—C14—H14A	116.9
C4—C3—H3B	109.7	C20—C15—C16	118.44 (15)
H3A—C3—H3B	108.2	C20—C15—C14	119.36 (15)
C3—C4—C5	111.17 (17)	C16—C15—C14	122.20 (15)
C3—C4—H4A	109.4	C17—C16—C15	120.77 (16)
C5—C4—H4A	109.4	C17—C16—H16A	119.6
C3—C4—H4B	109.4	C15—C16—H16A	119.6
C5—C4—H4B	109.4	C18—C17—C16	120.84 (16)
H4A—C4—H4B	108.0	C18—C17—H17A	119.6
N1—C5—C4	111.55 (16)	C16—C17—H17A	119.6
N1—C5—H5A	109.3	C17—C18—C19	118.19 (16)
C4—C5—H5A	109.3	C17—C18—H18A	120.9
N1—C5—H5B	109.3	C19—C18—H18A	120.9
C4—C5—H5B	109.3	C20—C19—C18	122.36 (16)
H5A—C5—H5B	108.0	C20—C19—N2	119.06 (15)
N1—C6—C11	122.43 (16)	C18—C19—N2	118.56 (15)
N1—C6—C7	120.46 (15)	C19—C20—C15	119.38 (15)
C11—C6—C7	117.06 (15)	C19—C20—H20A	120.3
C8—C7—C6	120.87 (15)	C15—C20—H20A	120.3
C8—C7—H7A	119.6
C6—N1—C1—C2	160.67 (19)	C8—C9—C12—O1	7.8 (3)
C5—N1—C1—C2	−54.9 (2)	C10—C9—C12—C13	10.0 (3)
N1—C1—C2—C3	54.1 (3)	C8—C9—C12—C13	−173.55 (17)
C1—C2—C3—C4	−53.8 (3)	O1—C12—C13—C14	4.7 (3)
C2—C3—C4—C5	54.8 (2)	C9—C12—C13—C14	−174.04 (18)
C6—N1—C5—C4	−159.97 (17)	C12—C13—C14—C15	−179.56 (17)
C1—N1—C5—C4	55.8 (2)	C13—C14—C15—C20	164.14 (19)
C3—C4—C5—N1	−56.2 (2)	C13—C14—C15—C16	−16.6 (3)
C5—N1—C6—C11	1.4 (3)	C20—C15—C16—C17	−0.2 (3)
C1—N1—C6—C11	143.41 (19)	C14—C15—C16—C17	−179.45 (17)
C5—N1—C6—C7	178.68 (17)	C15—C16—C17—C18	−1.0 (3)
C1—N1—C6—C7	−39.3 (3)	C16—C17—C18—C19	1.5 (3)
N1—C6—C7—C8	−178.05 (17)	C17—C18—C19—C20	−0.7 (3)
C11—C6—C7—C8	−0.6 (3)	C17—C18—C19—N2	177.91 (16)
C6—C7—C8—C9	0.1 (3)	O2—N2—C19—C20	−174.07 (18)
C7—C8—C9—C10	0.9 (3)	O3—N2—C19—C20	6.5 (3)
C7—C8—C9—C12	−175.81 (17)	O2—N2—C19—C18	7.2 (3)
C8—C9—C10—C11	−1.4 (3)	O3—N2—C19—C18	−172.18 (17)
C12—C9—C10—C11	175.06 (17)	C18—C19—C20—C15	−0.5 (3)
C9—C10—C11—C6	0.9 (3)	N2—C19—C20—C15	−179.10 (16)
N1—C6—C11—C10	177.47 (17)	C16—C15—C20—C19	0.9 (3)
C7—C6—C11—C10	0.1 (3)	C14—C15—C20—C19	−179.82 (17)
C10—C9—C12—O1	−168.65 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3i	0.93	2.55	3.441 (2)	161
C16—H16A···O1ii	0.93	2.45	3.358 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3i	0.93	2.55	3.441 (2)	161
C16—H16A⋯O1ii	0.93	2.45	3.358 (2)	164

Symmetry codes: (i) ; (ii) .