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

The piperidine ring in the title compound, C(21)H(23)NO(2), is in a slightly distorted chair conformation. The dihedral angle between the two benzene rings is 5.6 (4)°. The dihedral angles between the propenone unit and the benzene and meth-oxy-substituted benzene rings are 5.6 (7) and 10.7 (8)°, respectively. Weak inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions contribute to the stability of the crystal structure.

Related literature

For the synthesis and biological evaluation of simple meth­oxy­lated chalcones as anti­cancer, anti-inflammatory and anti­oxidant agents, see: Bandgar et al. (2010 ▶). For anti-inflammatory chalcones, see: Nowakowska (2007 ▶). For related structures, see: Ahmad et al.(2010 ▶); Arai et al.(1994 ▶); Jasinski et al. (2010 ▶); Li et al. (1992 ▶); Patil et al. (2007 ▶); Shettigar et al. (2006 ▶). For standard bond lengths, see; Allen et al. (1987 ▶).

Experimental

Crystal data

C21H23NO2

M = 321.40

Triclinic,

a = 6.0963 (11) Å

b = 10.985 (2) Å

c = 13.133 (3) Å

α = 74.188 (3)°

β = 88.674 (3)°

γ = 77.393 (3)°

V = 825.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.47 × 0.36 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.962, T max = 0.983

10674 measured reflections

4861 independent reflections

3562 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.151

S = 1.05

4861 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810026218/lh5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026218/lh5070Isup2.hkl

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

C21H23NO2	Z = 2
Mr = 321.40	F(000) = 344
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0963 (11) Å	Cell parameters from 1958 reflections
b = 10.985 (2) Å	θ = 2.2–30.9°
c = 13.133 (3) Å	µ = 0.08 mm−1
α = 74.188 (3)°	T = 100 K
β = 88.674 (3)°	Block, red
γ = 77.393 (3)°	0.47 × 0.36 × 0.21 mm
V = 825.2 (3) Å3

Bruker APEXII CCD diffractometer	4861 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 31.3°, θmin = 1.6°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −8→8
Tmin = 0.962, Tmax = 0.983	k = −15→15
10674 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.1716P] where P = (Fo2 + 2Fc2)/3
4861 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.23178 (16)	0.88147 (10)	−0.30730 (7)	0.0256 (2)
O2	1.10171 (16)	0.82032 (10)	0.20063 (7)	0.0233 (2)
N1	0.76112 (17)	0.61303 (11)	0.66686 (8)	0.0172 (2)
C1	0.8660 (2)	0.75063 (12)	0.33849 (9)	0.0166 (2)
C2	1.0241 (2)	0.74601 (13)	0.41547 (10)	0.0197 (3)
H2	1.1548	0.7748	0.3940	0.024*
C3	0.9928 (2)	0.70016 (13)	0.52239 (10)	0.0201 (3)
H3	1.1021	0.6994	0.5710	0.024*
C4	0.7989 (2)	0.65444 (12)	0.55956 (9)	0.0168 (2)
C5	0.6400 (2)	0.65849 (13)	0.48138 (10)	0.0208 (3)
H5	0.5103	0.6282	0.5022	0.025*
C6	0.6729 (2)	0.70647 (13)	0.37468 (10)	0.0199 (3)
H6	0.5630	0.7094	0.3256	0.024*
C7	0.9508 (2)	0.59163 (14)	0.74157 (10)	0.0202 (3)
H7A	1.0243	0.6641	0.7201	0.024*
H7B	1.0594	0.5139	0.7385	0.024*
C8	0.8785 (2)	0.57739 (14)	0.85498 (10)	0.0210 (3)
H8A	0.7896	0.6599	0.8606	0.025*
H8B	1.0111	0.5548	0.9015	0.025*
C9	0.7413 (2)	0.47408 (13)	0.89082 (10)	0.0204 (3)
H9A	0.8332	0.3896	0.8921	0.025*
H9B	0.6895	0.4714	0.9616	0.025*
C10	0.5413 (2)	0.50756 (13)	0.81348 (9)	0.0194 (3)
H10A	0.4555	0.4405	0.8336	0.023*
H10B	0.4440	0.5888	0.8171	0.023*
C11	0.6156 (2)	0.51976 (13)	0.70057 (10)	0.0187 (3)
H11B	0.6961	0.4354	0.6951	0.022*
H11A	0.4836	0.5471	0.6532	0.022*
C12	0.9153 (2)	0.79733 (12)	0.22544 (9)	0.0174 (2)
C13	0.7416 (2)	0.81181 (12)	0.14373 (10)	0.0182 (3)
H13	0.6061	0.7885	0.1641	0.022*
C14	0.7769 (2)	0.85811 (12)	0.04061 (10)	0.0179 (3)
H14	0.9108	0.8853	0.0243	0.021*
C15	0.6283 (2)	0.87041 (12)	−0.04869 (9)	0.0174 (2)
C16	0.4309 (2)	0.82206 (13)	−0.03711 (10)	0.0195 (3)
H16	0.3856	0.7857	0.0304	0.023*
C17	0.3037 (2)	0.82786 (13)	−0.12444 (10)	0.0202 (3)
H17	0.1744	0.7948	−0.1154	0.024*
C18	0.3679 (2)	0.88308 (13)	−0.22624 (10)	0.0198 (3)
C19	0.5590 (2)	0.93488 (13)	−0.23992 (10)	0.0210 (3)
H19	0.6008	0.9739	−0.3074	0.025*
C20	0.6865 (2)	0.92747 (12)	−0.15117 (10)	0.0190 (3)
H20	0.8146	0.9616	−0.1604	0.023*
C21	0.3004 (3)	0.93119 (15)	−0.41233 (10)	0.0265 (3)
H21A	0.3054	1.0207	−0.4238	0.040*
H21B	0.1949	0.9240	−0.4624	0.040*
H21C	0.4470	0.8823	−0.4214	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0261 (5)	0.0332 (6)	0.0188 (5)	−0.0104 (4)	−0.0024 (4)	−0.0061 (4)
O2	0.0210 (5)	0.0296 (5)	0.0216 (5)	−0.0118 (4)	0.0029 (4)	−0.0060 (4)
N1	0.0154 (5)	0.0228 (6)	0.0143 (5)	−0.0079 (4)	−0.0008 (4)	−0.0038 (4)
C1	0.0178 (6)	0.0159 (6)	0.0169 (6)	−0.0039 (4)	0.0006 (4)	−0.0054 (4)
C2	0.0153 (6)	0.0257 (7)	0.0190 (6)	−0.0080 (5)	0.0009 (4)	−0.0047 (5)
C3	0.0164 (6)	0.0268 (7)	0.0173 (6)	−0.0080 (5)	−0.0019 (5)	−0.0036 (5)
C4	0.0157 (6)	0.0182 (6)	0.0166 (6)	−0.0035 (4)	−0.0005 (4)	−0.0050 (5)
C5	0.0161 (6)	0.0295 (7)	0.0192 (6)	−0.0103 (5)	0.0014 (5)	−0.0065 (5)
C6	0.0186 (6)	0.0262 (7)	0.0168 (6)	−0.0085 (5)	−0.0009 (5)	−0.0064 (5)
C7	0.0172 (6)	0.0281 (7)	0.0171 (6)	−0.0097 (5)	−0.0012 (4)	−0.0054 (5)
C8	0.0211 (6)	0.0274 (7)	0.0167 (6)	−0.0094 (5)	−0.0003 (5)	−0.0066 (5)
C9	0.0206 (6)	0.0244 (7)	0.0154 (6)	−0.0059 (5)	0.0011 (5)	−0.0032 (5)
C10	0.0167 (6)	0.0240 (6)	0.0174 (6)	−0.0068 (5)	0.0010 (4)	−0.0034 (5)
C11	0.0166 (6)	0.0222 (6)	0.0183 (6)	−0.0072 (5)	−0.0004 (5)	−0.0048 (5)
C12	0.0201 (6)	0.0161 (6)	0.0163 (6)	−0.0044 (5)	0.0000 (5)	−0.0047 (5)
C13	0.0180 (6)	0.0190 (6)	0.0183 (6)	−0.0054 (5)	0.0003 (5)	−0.0052 (5)
C14	0.0177 (6)	0.0179 (6)	0.0185 (6)	−0.0039 (5)	0.0002 (5)	−0.0057 (5)
C15	0.0187 (6)	0.0154 (6)	0.0182 (6)	−0.0036 (4)	0.0007 (4)	−0.0048 (5)
C16	0.0201 (6)	0.0204 (6)	0.0177 (6)	−0.0057 (5)	0.0031 (5)	−0.0039 (5)
C17	0.0175 (6)	0.0213 (6)	0.0224 (6)	−0.0058 (5)	0.0015 (5)	−0.0057 (5)
C18	0.0201 (6)	0.0210 (6)	0.0182 (6)	−0.0031 (5)	−0.0016 (5)	−0.0062 (5)
C19	0.0226 (6)	0.0219 (6)	0.0177 (6)	−0.0064 (5)	0.0012 (5)	−0.0029 (5)
C20	0.0188 (6)	0.0181 (6)	0.0197 (6)	−0.0052 (5)	0.0020 (5)	−0.0038 (5)
C21	0.0305 (8)	0.0312 (8)	0.0177 (6)	−0.0068 (6)	−0.0013 (5)	−0.0063 (5)

O1—C18	1.3711 (15)	C9—H9B	0.9700
O1—C21	1.4277 (16)	C10—C11	1.5194 (17)
O2—C12	1.2346 (15)	C10—H10A	0.9700
N1—C4	1.3882 (16)	C10—H10B	0.9700
N1—C7	1.4706 (15)	C11—H11B	0.9700
N1—C11	1.4713 (16)	C11—H11A	0.9700
C1—C6	1.3942 (17)	C12—C13	1.4779 (17)
C1—C2	1.3963 (16)	C13—C14	1.3408 (17)
C1—C12	1.4797 (17)	C13—H13	0.9300
C2—C3	1.3806 (17)	C14—C15	1.4575 (17)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.4097 (17)	C15—C20	1.3948 (17)
C3—H3	0.9300	C15—C16	1.4071 (17)
C4—C5	1.4130 (16)	C16—C17	1.3785 (17)
C5—C6	1.3830 (17)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.3949 (18)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.5197 (17)	C18—C19	1.3920 (18)
C7—H7A	0.9700	C19—C20	1.3897 (17)
C7—H7B	0.9700	C19—H19	0.9300
C8—C9	1.5212 (18)	C20—H20	0.9300
C8—H8A	0.9700	C21—H21A	0.9600
C8—H8B	0.9700	C21—H21B	0.9600
C9—C10	1.5207 (17)	C21—H21C	0.9600
C9—H9A	0.9700
C18—O1—C21	116.56 (10)	C11—C10—H10B	109.3
C4—N1—C7	117.45 (10)	C9—C10—H10B	109.3
C4—N1—C11	117.85 (10)	H10A—C10—H10B	108.0
C7—N1—C11	113.84 (10)	N1—C11—C10	112.56 (10)
C6—C1—C2	116.73 (11)	N1—C11—H11B	109.1
C6—C1—C12	124.41 (11)	C10—C11—H11B	109.1
C2—C1—C12	118.84 (11)	N1—C11—H11A	109.1
C3—C2—C1	122.16 (11)	C10—C11—H11A	109.1
C3—C2—H2	118.9	H11B—C11—H11A	107.8
C1—C2—H2	118.9	O2—C12—C13	121.02 (11)
C2—C3—C4	121.43 (11)	O2—C12—C1	119.88 (11)
C2—C3—H3	119.3	C13—C12—C1	119.07 (11)
C4—C3—H3	119.3	C14—C13—C12	120.87 (12)
N1—C4—C3	121.98 (11)	C14—C13—H13	119.6
N1—C4—C5	121.74 (11)	C12—C13—H13	119.6
C3—C4—C5	116.22 (11)	C13—C14—C15	127.06 (12)
C6—C5—C4	121.47 (12)	C13—C14—H14	116.5
C6—C5—H5	119.3	C15—C14—H14	116.5
C4—C5—H5	119.3	C20—C15—C16	117.66 (11)
C5—C6—C1	121.97 (11)	C20—C15—C14	119.35 (11)
C5—C6—H6	119.0	C16—C15—C14	122.93 (11)
C1—C6—H6	119.0	C17—C16—C15	120.88 (12)
N1—C7—C8	112.76 (10)	C17—C16—H16	119.6
N1—C7—H7A	109.0	C15—C16—H16	119.6
C8—C7—H7A	109.0	C16—C17—C18	120.37 (12)
N1—C7—H7B	109.0	C16—C17—H17	119.8
C8—C7—H7B	109.0	C18—C17—H17	119.8
H7A—C7—H7B	107.8	O1—C18—C19	124.56 (12)
C7—C8—C9	112.12 (10)	O1—C18—C17	115.48 (11)
C7—C8—H8A	109.2	C19—C18—C17	119.96 (11)
C9—C8—H8A	109.2	C20—C19—C18	119.01 (12)
C7—C8—H8B	109.2	C20—C19—H19	120.5
C9—C8—H8B	109.2	C18—C19—H19	120.5
H8A—C8—H8B	107.9	C19—C20—C15	122.08 (12)
C10—C9—C8	108.32 (10)	C19—C20—H20	119.0
C10—C9—H9A	110.0	C15—C20—H20	119.0
C8—C9—H9A	110.0	O1—C21—H21A	109.5
C10—C9—H9B	110.0	O1—C21—H21B	109.5
C8—C9—H9B	110.0	H21A—C21—H21B	109.5
H9A—C9—H9B	108.4	O1—C21—H21C	109.5
C11—C10—C9	111.56 (10)	H21A—C21—H21C	109.5
C11—C10—H10A	109.3	H21B—C21—H21C	109.5
C9—C10—H10A	109.3
C6—C1—C2—C3	0.01 (19)	C6—C1—C12—O2	−171.55 (13)
C12—C1—C2—C3	−178.13 (12)	C2—C1—C12—O2	6.44 (18)
C1—C2—C3—C4	0.5 (2)	C6—C1—C12—C13	6.57 (19)
C7—N1—C4—C3	−12.83 (18)	C2—C1—C12—C13	−175.44 (11)
C11—N1—C4—C3	−154.97 (12)	O2—C12—C13—C14	−4.24 (19)
C7—N1—C4—C5	170.04 (11)	C1—C12—C13—C14	177.66 (11)
C11—N1—C4—C5	27.90 (18)	C12—C13—C14—C15	176.00 (11)
C2—C3—C4—N1	−177.33 (12)	C13—C14—C15—C20	176.56 (12)
C2—C3—C4—C5	−0.05 (19)	C13—C14—C15—C16	−6.3 (2)
N1—C4—C5—C6	176.42 (12)	C20—C15—C16—C17	1.80 (19)
C3—C4—C5—C6	−0.9 (2)	C14—C15—C16—C17	−175.43 (12)
C4—C5—C6—C1	1.4 (2)	C15—C16—C17—C18	−0.6 (2)
C2—C1—C6—C5	−0.95 (19)	C21—O1—C18—C19	3.18 (19)
C12—C1—C6—C5	177.09 (12)	C21—O1—C18—C17	−176.80 (11)
C4—N1—C7—C8	166.66 (11)	C16—C17—C18—O1	178.77 (11)
C11—N1—C7—C8	−49.73 (15)	C16—C17—C18—C19	−1.2 (2)
N1—C7—C8—C9	53.10 (15)	O1—C18—C19—C20	−178.31 (12)
C7—C8—C9—C10	−55.90 (15)	C17—C18—C19—C20	1.7 (2)
C8—C9—C10—C11	56.61 (14)	C18—C19—C20—C15	−0.4 (2)
C4—N1—C11—C10	−165.90 (11)	C16—C15—C20—C19	−1.33 (19)
C7—N1—C11—C10	50.64 (15)	C14—C15—C20—C19	176.00 (12)
C9—C10—C11—N1	−54.75 (15)

Cg2 and Cg3 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2i	0.93	2.47	3.2105 (16)	137
C8—H8A···Cg3ii	0.97	2.66	3.623 (2)	171
C21—H21A···Cg2iii	0.96	2.90	3.823 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.93	2.47	3.2105 (16)	137
C8—H8A⋯Cg3ii	0.97	2.66	3.623 (2)	171
C21—H21A⋯Cg2iii	0.96	2.90	3.823 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) .