(1E,4E)-1-(2-Nitro-phen-yl)-5-(2,6,6-trimethyl-cyclo-hex-1-en-1-yl)penta-1,4-dien-3-one.

In the title curcumin-ionone derivative, C(20)H(23)NO(3), the dihedral angle between the cyclo-hexene and benzene rings is 21.03 (8)°, with both double bonds in the inter-linking olefinic chain adopting E conformations. Two of the methyl-ene groups of the β-ionone ring are disordered over two sets of sites with occupancy ratios of 0.50:0.50 and 0.60:0.40. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into zigzag chains extending along the b axis.

Related literature

For related structures, see: Liang et al. (2007 ▶); Zhang et al. (2012 ▶). For background to the biological properties of curcumin–ionone derivatives, see: Asokkumar et al. (2012 ▶); Hsu & Cheng (2007 ▶); Kuttan et al. (1985 ▶); Zhao, Cai et al. (2010 ▶); Zhao, Yang et al. (2010 ▶).

Experimental

Crystal data

C20H23NO3

M = 325.39

Monoclinic,

a = 7.2941 (6) Å

b = 19.2984 (15) Å

c = 12.7491 (10) Å

β = 92.892 (2)°

V = 1792.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.33 × 0.25 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.533, T max = 1.000

10762 measured reflections

3512 independent reflections

2629 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.144

S = 1.06

3512 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022453/zs2210sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022453/zs2210Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022453/zs2210Isup3.cml

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

C20H23NO3	F(000) = 696
Mr = 325.39	Dx = 1.206 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2030 reflections
a = 7.2941 (6) Å	θ = 5.3–42.7°
b = 19.2984 (15) Å	µ = 0.08 mm−1
c = 12.7491 (10) Å	T = 293 K
β = 92.892 (2)°	Prismatic, green
V = 1792.3 (2) Å3	0.33 × 0.25 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.533, Tmax = 1.000	k = −23→19
10762 measured reflections	l = −15→15

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.407P] where P = (Fo2 + 2Fc2)/3
3512 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.14 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 Rfactors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating Rfactors (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	Occ. (<1)
N1	0.0393 (2)	0.29601 (10)	0.52846 (12)	0.0552 (5)
O1	0.67912 (19)	0.20268 (9)	0.48739 (10)	0.0668 (5)
O2	0.1133 (2)	0.24512 (10)	0.56699 (11)	0.0761 (5)
O3	−0.0291 (3)	0.34121 (11)	0.57997 (12)	0.0906 (6)
C1	0.6322 (2)	0.18763 (10)	0.39702 (13)	0.0458 (5)
C2	0.4555 (3)	0.21296 (11)	0.34870 (14)	0.0486 (5)
H2	0.4212	0.1990	0.2807	0.058*
C3	0.3453 (2)	0.25430 (10)	0.39799 (14)	0.0447 (4)
H3	0.3813	0.2676	0.4661	0.054*
C4	0.1692 (2)	0.28111 (9)	0.35343 (13)	0.0410 (4)
C5	0.0265 (2)	0.30303 (9)	0.41389 (13)	0.0413 (4)
C6	−0.1358 (3)	0.32970 (10)	0.37105 (15)	0.0487 (5)
H6	−0.2263	0.3451	0.4143	0.058*
C7	−0.1623 (3)	0.33330 (10)	0.26406 (15)	0.0530 (5)
H7	−0.2733	0.3493	0.2341	0.064*
C8	−0.0240 (3)	0.31316 (11)	0.20119 (15)	0.0536 (5)
H8	−0.0411	0.3161	0.1285	0.064*
C9	0.1391 (3)	0.28873 (10)	0.24514 (14)	0.0489 (5)
H9	0.2323	0.2769	0.2014	0.059*
C10	0.7434 (3)	0.14433 (10)	0.33055 (14)	0.0468 (5)
H10	0.7035	0.1366	0.2611	0.056*
C11	0.8992 (3)	0.11580 (10)	0.36674 (14)	0.0465 (5)
H11	0.9313	0.1265	0.4364	0.056*
C12	1.0294 (3)	0.07069 (10)	0.31721 (15)	0.0468 (5)
C13	1.1754 (3)	0.04690 (10)	0.37653 (17)	0.0540 (5)
C14	1.3181 (3)	0.00004 (14)	0.3345 (2)	0.0806 (8)
H14A	1.3006	−0.0464	0.3612	0.097*	0.60
H14B	1.4386	0.0158	0.3598	0.097*	0.60
H14C	1.3564	−0.0326	0.3880	0.097*	0.40
H14D	1.4220	0.0272	0.3161	0.097*	0.40
C15	1.3113 (7)	−0.0023 (4)	0.2146 (5)	0.0806 (15)	0.60
H15A	1.3534	0.0414	0.1868	0.097*	0.60
H15B	1.3898	−0.0390	0.1908	0.097*	0.60
C16	1.1135 (8)	−0.0156 (3)	0.1771 (5)	0.0617 (14)	0.50
H16A	1.0659	−0.0555	0.2130	0.074*	0.50
H16B	1.1065	−0.0249	0.1022	0.074*	0.50
C15'	1.2479 (15)	−0.0375 (4)	0.2337 (8)	0.082 (3)	0.40
H15C	1.3461	−0.0635	0.2035	0.099*	0.40
H15D	1.1491	−0.0691	0.2485	0.099*	0.40
C16'	1.1810 (10)	0.0186 (4)	0.1612 (5)	0.0762 (16)	0.50
H16C	1.1588	0.0000	0.0910	0.091*	0.50
H16D	1.2736	0.0546	0.1582	0.091*	0.50
C17	0.9974 (3)	0.05041 (11)	0.20138 (16)	0.0582 (6)
C18	1.2140 (3)	0.06430 (14)	0.49096 (18)	0.0751 (7)
H18A	1.1982	0.1132	0.5013	0.113*
H18B	1.3378	0.0515	0.5115	0.113*
H18C	1.1305	0.0393	0.5328	0.113*
C19	0.8125 (4)	0.01320 (13)	0.1825 (2)	0.0835 (8)
H19A	0.7145	0.0462	0.1855	0.125*
H19B	0.7994	−0.0214	0.2357	0.125*
H19C	0.8082	−0.0085	0.1147	0.125*
C20	1.0017 (3)	0.11384 (14)	0.13065 (17)	0.0729 (7)
H20A	0.9097	0.1462	0.1504	0.109*
H20B	0.9777	0.1001	0.0589	0.109*
H20C	1.1205	0.1352	0.1381	0.109*

	U11	U22	U33	U12	U13	U23
N1	0.0414 (9)	0.0854 (13)	0.0391 (9)	0.0153 (9)	0.0032 (7)	−0.0070 (9)
O1	0.0511 (9)	0.1112 (13)	0.0381 (8)	0.0193 (8)	0.0009 (6)	−0.0105 (8)
O2	0.0691 (11)	0.1120 (14)	0.0473 (8)	0.0321 (10)	0.0044 (7)	0.0175 (9)
O3	0.0924 (13)	0.1301 (16)	0.0492 (9)	0.0438 (12)	0.0039 (8)	−0.0284 (10)
C1	0.0395 (10)	0.0623 (12)	0.0361 (10)	0.0027 (9)	0.0070 (8)	0.0016 (8)
C2	0.0431 (10)	0.0630 (12)	0.0396 (10)	0.0048 (9)	0.0018 (8)	−0.0062 (9)
C3	0.0395 (10)	0.0578 (12)	0.0370 (9)	0.0027 (8)	0.0034 (8)	−0.0042 (8)
C4	0.0409 (10)	0.0440 (10)	0.0382 (9)	0.0021 (8)	0.0027 (8)	−0.0044 (7)
C5	0.0402 (10)	0.0475 (10)	0.0359 (9)	0.0036 (8)	0.0009 (7)	−0.0039 (8)
C6	0.0445 (11)	0.0530 (12)	0.0487 (11)	0.0098 (9)	0.0025 (9)	−0.0063 (9)
C7	0.0513 (12)	0.0538 (12)	0.0527 (11)	0.0118 (9)	−0.0086 (9)	0.0015 (9)
C8	0.0625 (13)	0.0603 (12)	0.0372 (10)	0.0070 (10)	−0.0048 (9)	0.0028 (9)
C9	0.0524 (12)	0.0562 (12)	0.0388 (10)	0.0058 (9)	0.0083 (8)	−0.0018 (8)
C10	0.0419 (11)	0.0607 (12)	0.0377 (9)	0.0065 (9)	0.0013 (8)	−0.0019 (8)
C11	0.0439 (11)	0.0551 (11)	0.0405 (9)	0.0036 (9)	0.0021 (8)	0.0018 (8)
C12	0.0426 (10)	0.0472 (10)	0.0507 (11)	0.0051 (8)	0.0030 (8)	0.0026 (8)
C13	0.0448 (11)	0.0490 (11)	0.0679 (13)	0.0027 (9)	−0.0014 (10)	0.0089 (10)
C14	0.0597 (15)	0.0751 (16)	0.106 (2)	0.0257 (13)	−0.0002 (14)	0.0025 (15)
C15	0.059 (3)	0.081 (4)	0.102 (4)	0.028 (3)	0.016 (3)	−0.010 (3)
C16	0.060 (4)	0.051 (3)	0.075 (3)	0.001 (3)	0.015 (3)	−0.012 (3)
C15'	0.086 (6)	0.048 (4)	0.115 (6)	0.025 (4)	0.027 (5)	−0.001 (4)
C16'	0.074 (5)	0.076 (4)	0.079 (4)	0.019 (4)	0.017 (3)	−0.018 (3)
C17	0.0579 (13)	0.0619 (13)	0.0546 (12)	0.0157 (11)	0.0029 (10)	−0.0105 (10)
C18	0.0665 (15)	0.0839 (17)	0.0724 (15)	0.0090 (13)	−0.0204 (12)	0.0140 (13)
C19	0.112 (2)	0.0615 (15)	0.0759 (16)	−0.0227 (15)	−0.0086 (15)	−0.0128 (12)
C20	0.0743 (16)	0.0969 (18)	0.0482 (12)	−0.0140 (14)	0.0103 (11)	0.0054 (12)

N1—O2	1.213 (2)	C14—C15'	1.539 (10)
N1—O3	1.214 (2)	C14—H14A	0.9700
N1—C5	1.465 (2)	C14—H14B	0.9700
O1—C1	1.220 (2)	C14—H14C	0.9600
C1—C10	1.464 (3)	C14—H14D	0.9600
C1—C2	1.483 (3)	C15—C16	1.519 (8)
C2—C3	1.314 (3)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.472 (3)	C16—C17	1.569 (6)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.392 (2)	C16—H16B	0.9700
C4—C9	1.395 (2)	C15'—C16'	1.490 (11)
C5—C6	1.378 (2)	C15'—H15C	0.9700
C6—C7	1.370 (3)	C15'—H15D	0.9700
C6—H6	0.9300	C16'—C17	1.582 (6)
C7—C8	1.376 (3)	C16'—H16C	0.9700
C7—H7	0.9300	C16'—H16D	0.9700
C8—C9	1.372 (3)	C17—C20	1.522 (3)
C8—H8	0.9300	C17—C19	1.536 (3)
C9—H9	0.9300	C18—H18A	0.9600
C10—C11	1.325 (3)	C18—H18B	0.9600
C10—H10	0.9300	C18—H18C	0.9600
C11—C12	1.455 (3)	C19—H19A	0.9600
C11—H11	0.9300	C19—H19B	0.9600
C12—C13	1.355 (3)	C19—H19C	0.9600
C12—C17	1.534 (3)	C20—H20A	0.9600
C13—C14	1.498 (3)	C20—H20B	0.9600
C13—C18	1.510 (3)	C20—H20C	0.9600
C14—C15	1.527 (7)
O2—N1—O3	123.32 (17)	C15'—C14—H14D	106.7
O2—N1—C5	118.91 (16)	H14C—C14—H14D	109.1
O3—N1—C5	117.74 (17)	C16—C15—C14	107.6 (4)
O1—C1—C10	123.06 (17)	C16—C15—H15A	110.2
O1—C1—C2	120.66 (17)	C14—C15—H15A	110.2
C10—C1—C2	116.28 (15)	C16—C15—H15B	110.2
C3—C2—C1	122.75 (17)	C14—C15—H15B	110.2
C3—C2—H2	118.6	H15A—C15—H15B	108.5
C1—C2—H2	118.6	C15—C16—C17	108.3 (4)
C2—C3—C4	124.85 (17)	C15—C16—H16A	110.0
C2—C3—H3	117.6	C17—C16—H16A	110.0
C4—C3—H3	117.6	C15—C16—H16B	110.0
C5—C4—C9	115.53 (16)	C17—C16—H16B	110.0
C5—C4—C3	123.75 (15)	H16A—C16—H16B	108.4
C9—C4—C3	120.67 (16)	C16'—C15'—C14	105.1 (6)
C6—C5—C4	123.06 (16)	C16'—C15'—H15C	110.7
C6—C5—N1	116.09 (16)	C14—C15'—H15C	110.7
C4—C5—N1	120.80 (15)	C16'—C15'—H15D	110.7
C7—C6—C5	119.28 (18)	C14—C15'—H15D	110.7
C7—C6—H6	120.4	H15C—C15'—H15D	108.8
C5—C6—H6	120.4	C15'—C16'—C17	109.7 (6)
C6—C7—C8	119.66 (18)	C15'—C16'—H16C	109.7
C6—C7—H7	120.2	C17—C16'—H16C	109.7
C8—C7—H7	120.2	C15'—C16'—H16D	109.7
C9—C8—C7	120.33 (17)	C17—C16'—H16D	109.7
C9—C8—H8	119.8	H16C—C16'—H16D	108.2
C7—C8—H8	119.8	C20—C17—C12	111.00 (18)
C8—C9—C4	122.04 (18)	C20—C17—C19	109.12 (19)
C8—C9—H9	119.0	C12—C17—C19	111.07 (19)
C4—C9—H9	119.0	C20—C17—C16	120.6 (3)
C11—C10—C1	121.74 (17)	C12—C17—C16	109.9 (3)
C11—C10—H10	119.1	C19—C17—C16	93.9 (3)
C1—C10—H10	119.1	C20—C17—C16'	94.4 (3)
C10—C11—C12	131.64 (18)	C12—C17—C16'	108.7 (3)
C10—C11—H11	114.2	C19—C17—C16'	121.3 (3)
C12—C11—H11	114.2	C13—C18—H18A	109.5
C13—C12—C11	118.18 (18)	C13—C18—H18B	109.5
C13—C12—C17	121.84 (18)	H18A—C18—H18B	109.5
C11—C12—C17	119.97 (16)	C13—C18—H18C	109.5
C12—C13—C14	123.1 (2)	H18A—C18—H18C	109.5
C12—C13—C18	124.52 (19)	H18B—C18—H18C	109.5
C14—C13—C18	112.42 (18)	C17—C19—H19A	109.5
C13—C14—C15	112.8 (3)	C17—C19—H19B	109.5
C13—C14—C15'	112.0 (4)	H19A—C19—H19B	109.5
C13—C14—H14A	109.0	C17—C19—H19C	109.5
C15—C14—H14A	109.0	H19A—C19—H19C	109.5
C13—C14—H14B	109.0	H19B—C19—H19C	109.5
C15—C14—H14B	109.0	C17—C20—H20A	109.5
C15'—C14—H14B	133.1	C17—C20—H20B	109.5
H14A—C14—H14B	107.8	H20A—C20—H20B	109.5
C13—C14—H14C	108.9	C17—C20—H20C	109.5
C15'—C14—H14C	110.9	H20A—C20—H20C	109.5
C13—C14—H14D	109.2	H20B—C20—H20C	109.5
O1—C1—C2—C3	2.7 (3)	C17—C12—C13—C18	−179.4 (2)
C10—C1—C2—C3	−177.46 (19)	C12—C13—C14—C15	15.3 (4)
C1—C2—C3—C4	179.70 (17)	C18—C13—C14—C15	−164.4 (3)
C2—C3—C4—C5	156.1 (2)	C12—C13—C14—C15'	−20.1 (5)
C2—C3—C4—C9	−26.6 (3)	C18—C13—C14—C15'	160.1 (4)
C9—C4—C5—C6	0.9 (3)	C13—C14—C15—C16	−49.6 (6)
C3—C4—C5—C6	178.25 (18)	C15'—C14—C15—C16	46.0 (7)
C9—C4—C5—N1	178.32 (17)	C14—C15—C16—C17	68.9 (7)
C3—C4—C5—N1	−4.3 (3)	C13—C14—C15'—C16'	54.0 (8)
O2—N1—C5—C6	140.47 (19)	C15—C14—C15'—C16'	−44.3 (6)
O3—N1—C5—C6	−37.9 (3)	C14—C15'—C16'—C17	−71.5 (9)
O2—N1—C5—C4	−37.1 (3)	C13—C12—C17—C20	−118.2 (2)
O3—N1—C5—C4	144.5 (2)	C11—C12—C17—C20	62.8 (2)
C4—C5—C6—C7	2.0 (3)	C13—C12—C17—C19	120.2 (2)
N1—C5—C6—C7	−175.55 (18)	C11—C12—C17—C19	−58.8 (3)
C5—C6—C7—C8	−2.8 (3)	C13—C12—C17—C16	17.7 (4)
C6—C7—C8—C9	0.8 (3)	C11—C12—C17—C16	−161.3 (3)
C7—C8—C9—C4	2.2 (3)	C13—C12—C17—C16'	−15.7 (4)
C5—C4—C9—C8	−3.0 (3)	C11—C12—C17—C16'	165.3 (3)
C3—C4—C9—C8	179.57 (19)	C15—C16—C17—C20	78.9 (5)
O1—C1—C10—C11	3.4 (3)	C15—C16—C17—C12	−52.1 (6)
C2—C1—C10—C11	−176.50 (18)	C15—C16—C17—C19	−166.1 (5)
C1—C10—C11—C12	178.81 (19)	C15—C16—C17—C16'	41.5 (6)
C10—C11—C12—C13	−177.1 (2)	C15'—C16'—C17—C20	165.9 (7)
C10—C11—C12—C17	1.9 (3)	C15'—C16'—C17—C12	52.0 (7)
C11—C12—C13—C14	179.8 (2)	C15'—C16'—C17—C19	−78.5 (7)
C17—C12—C13—C14	0.8 (3)	C15'—C16'—C17—C16	−45.7 (7)
C11—C12—C13—C18	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.50	3.182 (2)	131
C9—H9···O1i	0.93	2.76	3.318 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.50	3.182 (2)	131

Symmetry code: (i) .