(E)-1-(4-Amino-phen-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Mol-ecules of the title amino-chalcone, C(18)H(19)NO(4), are twisted, with a dihedral angle of 11.26 (6)° between the 4-amino-phenyl and 2,4,5-trimeth-oxy-phenyl rings. The conformations of the three meth-oxy groups with respect to the benzene ring are slightly different. Two meth-oxy groups are almost coplanar with the attached benzene ring [C-O-C-C torsion angles of -1.45 (19) and 1.5 (2)°], while the third is (-)-synclinal with the attached benzene ring [C-O-C-C = -81.36 (17)°]. In the crystal structure, mol-ecules are stacked into columns along the b axis and mol-ecules in adjacent columns are linked by N-H⋯O hydrogen bonds into V-shaped double columns. Weak π-π inter-actions are also observed, with a centroid-centroid distance of 3.7532 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶, 2010 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Batovska et al. (2007 ▶); Jung et al. (2008 ▶); Kim et al. (2010 ▶); Nielsen et al. (2004 ▶); Niu et al. (2006 ▶); Romagnoli et al. (2008 ▶); Tewtrakul et al. (2003 ▶); Won et al. (2005 ▶); Xia et al. (2000 ▶).

Experimental

Crystal data

C18H19NO4

M = 313.34

Monoclinic,

a = 13.6117 (2) Å

b = 10.3540 (2) Å

c = 22.3920 (4) Å

β = 100.879 (1)°

V = 3099.11 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.38 × 0.32 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.991

19818 measured reflections

4506 independent reflections

3581 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.131

S = 1.05

4506 reflections

219 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536810026346/fj2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026346/fj2326Isup2.hkl

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

C18H19NO4	F(000) = 1328
Mr = 313.34	Dx = 1.343 Mg m−3
Monoclinic, C2/c	Melting point = 393–394 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.6117 (2) Å	Cell parameters from 4506 reflections
b = 10.3540 (2) Å	θ = 1.9–30.0°
c = 22.3920 (4) Å	µ = 0.10 mm−1
β = 100.879 (1)°	T = 100 K
V = 3099.11 (9) Å3	Block, orange
Z = 8	0.38 × 0.32 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	4506 independent reflections
Radiation source: sealed tube	3581 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.965, Tmax = 0.991	k = −14→12
19818 measured reflections	l = −31→31

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0552P)2 + 3.4363P] where P = (Fo2 + 2Fc2)/3
4506 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.43 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 120.0 (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	0.38020 (7)	0.71239 (11)	0.65434 (5)	0.0236 (2)
O2	0.40102 (7)	0.40284 (10)	0.49618 (5)	0.0226 (2)
O3	0.10593 (7)	0.26403 (10)	0.35317 (5)	0.0237 (2)
O4	−0.00667 (7)	0.42294 (10)	0.40878 (5)	0.0230 (2)
N1	0.09228 (9)	1.16277 (13)	0.71073 (6)	0.0226 (3)
H1N1	0.0289 (15)	1.1700 (18)	0.6971 (8)	0.028 (5)*
H2N1	0.1136 (15)	1.197 (2)	0.7468 (9)	0.036 (5)*
C1	0.23640 (9)	0.84035 (13)	0.65403 (6)	0.0165 (3)
C2	0.28745 (9)	0.92608 (13)	0.69789 (6)	0.0169 (3)
H2A	0.3552	0.9129	0.7131	0.020*
C3	0.23973 (10)	1.02891 (13)	0.71892 (6)	0.0174 (3)
H3A	0.2749	1.0829	0.7486	0.021*
C4	0.13779 (10)	1.05267 (13)	0.69558 (6)	0.0171 (3)
C5	0.08494 (9)	0.96364 (14)	0.65447 (6)	0.0183 (3)
H5A	0.0166	0.9746	0.6407	0.022*
C6	0.13318 (10)	0.86001 (14)	0.63425 (6)	0.0182 (3)
H6A	0.0968	0.8020	0.6070	0.022*
C7	0.29247 (10)	0.73650 (13)	0.63014 (6)	0.0177 (3)
C8	0.24234 (10)	0.66396 (14)	0.57644 (6)	0.0201 (3)
H8A	0.1762	0.6835	0.5598	0.024*
C9	0.28853 (9)	0.57075 (13)	0.55064 (6)	0.0177 (3)
H9A	0.3553	0.5549	0.5673	0.021*
C10	0.24334 (9)	0.49221 (13)	0.49882 (6)	0.0163 (3)
C11	0.30112 (9)	0.40495 (13)	0.47178 (6)	0.0174 (3)
C12	0.25784 (10)	0.32686 (13)	0.42310 (6)	0.0185 (3)
H12A	0.2973	0.2697	0.4059	0.022*
C13	0.15546 (10)	0.33465 (13)	0.40038 (6)	0.0181 (3)
C14	0.09645 (9)	0.42119 (13)	0.42698 (6)	0.0181 (3)
C15	0.14011 (10)	0.49721 (13)	0.47490 (6)	0.0177 (3)
H15A	0.1002	0.5538	0.4921	0.021*
C16	0.46300 (10)	0.31421 (15)	0.47127 (7)	0.0227 (3)
H16A	0.5310	0.3231	0.4922	0.034*
H16B	0.4590	0.3324	0.4288	0.034*
H16C	0.4406	0.2276	0.4760	0.034*
C17	0.16178 (11)	0.17238 (15)	0.32512 (7)	0.0249 (3)
H17A	0.1189	0.1338	0.2908	0.037*
H17B	0.1877	0.1065	0.3540	0.037*
H17C	0.2162	0.2155	0.3118	0.037*
C18	−0.04143 (12)	0.49413 (19)	0.35457 (8)	0.0338 (4)
H18A	−0.1129	0.5017	0.3482	0.051*
H18B	−0.0228	0.4500	0.3207	0.051*
H18C	−0.0120	0.5787	0.3582	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0160 (5)	0.0295 (6)	0.0228 (5)	0.0039 (4)	−0.0025 (4)	−0.0032 (4)
O2	0.0130 (4)	0.0288 (6)	0.0253 (5)	0.0038 (4)	0.0019 (4)	−0.0025 (4)
O3	0.0197 (5)	0.0270 (5)	0.0244 (5)	−0.0026 (4)	0.0043 (4)	−0.0092 (4)
O4	0.0132 (4)	0.0286 (6)	0.0263 (5)	−0.0023 (4)	0.0012 (4)	−0.0023 (4)
N1	0.0168 (6)	0.0277 (7)	0.0220 (6)	0.0043 (5)	0.0001 (4)	−0.0045 (5)
C1	0.0151 (6)	0.0176 (6)	0.0160 (6)	−0.0007 (5)	0.0009 (4)	0.0023 (5)
C2	0.0126 (5)	0.0202 (6)	0.0164 (6)	−0.0009 (5)	−0.0009 (4)	0.0036 (5)
C3	0.0157 (6)	0.0201 (6)	0.0151 (6)	−0.0029 (5)	−0.0004 (4)	0.0012 (5)
C4	0.0162 (6)	0.0200 (6)	0.0152 (6)	−0.0005 (5)	0.0035 (4)	0.0034 (5)
C5	0.0116 (5)	0.0230 (7)	0.0195 (6)	−0.0014 (5)	0.0003 (4)	0.0023 (5)
C6	0.0151 (6)	0.0206 (6)	0.0176 (6)	−0.0038 (5)	−0.0002 (4)	0.0006 (5)
C7	0.0160 (6)	0.0194 (6)	0.0170 (6)	−0.0002 (5)	0.0012 (5)	0.0022 (5)
C8	0.0151 (6)	0.0225 (7)	0.0203 (6)	0.0011 (5)	−0.0024 (5)	−0.0015 (5)
C9	0.0137 (5)	0.0220 (7)	0.0170 (6)	−0.0018 (5)	0.0019 (4)	0.0029 (5)
C10	0.0145 (6)	0.0184 (6)	0.0161 (6)	−0.0008 (5)	0.0034 (4)	0.0018 (5)
C11	0.0135 (5)	0.0202 (6)	0.0186 (6)	−0.0002 (5)	0.0034 (5)	0.0035 (5)
C12	0.0178 (6)	0.0186 (6)	0.0209 (6)	0.0013 (5)	0.0080 (5)	0.0005 (5)
C13	0.0190 (6)	0.0186 (6)	0.0174 (6)	−0.0038 (5)	0.0052 (5)	−0.0006 (5)
C14	0.0129 (6)	0.0208 (7)	0.0206 (6)	−0.0023 (5)	0.0033 (5)	0.0008 (5)
C15	0.0148 (6)	0.0187 (6)	0.0200 (6)	0.0003 (5)	0.0045 (5)	−0.0005 (5)
C16	0.0166 (6)	0.0260 (7)	0.0265 (7)	0.0058 (5)	0.0071 (5)	0.0040 (6)
C17	0.0281 (7)	0.0221 (7)	0.0260 (7)	−0.0023 (6)	0.0091 (6)	−0.0064 (6)
C18	0.0208 (7)	0.0432 (10)	0.0345 (9)	0.0005 (7)	−0.0023 (6)	0.0071 (7)

O1—C7	1.2400 (16)	C8—C9	1.3407 (19)
O2—C11	1.3666 (15)	C8—H8A	0.9300
O2—C16	1.4293 (17)	C9—C10	1.4549 (18)
O3—C13	1.3557 (16)	C9—H9A	0.9300
O3—C17	1.4329 (17)	C10—C15	1.4071 (18)
O4—C14	1.3859 (15)	C10—C11	1.4076 (18)
O4—C18	1.4228 (19)	C11—C12	1.3953 (19)
N1—C4	1.3704 (18)	C12—C13	1.3927 (18)
N1—H1N1	0.862 (19)	C12—H12A	0.9300
N1—H2N1	0.88 (2)	C13—C14	1.4083 (19)
C1—C6	1.4060 (18)	C14—C15	1.3724 (19)
C1—C2	1.4064 (18)	C15—H15A	0.9300
C1—C7	1.4760 (19)	C16—H16A	0.9600
C2—C3	1.3758 (19)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.4089 (18)	C17—H17A	0.9600
C3—H3A	0.9300	C17—H17B	0.9600
C4—C5	1.4016 (19)	C17—H17C	0.9600
C5—C6	1.378 (2)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—H6A	0.9300	C18—H18C	0.9600
C7—C8	1.4718 (19)
C11—O2—C16	118.06 (11)	C11—C10—C9	121.02 (12)
C13—O3—C17	118.17 (11)	O2—C11—C12	123.00 (12)
C14—O4—C18	114.38 (11)	O2—C11—C10	115.65 (12)
C4—N1—H1N1	117.0 (13)	C12—C11—C10	121.35 (12)
C4—N1—H2N1	118.4 (13)	C13—C12—C11	119.84 (12)
H1N1—N1—H2N1	115.1 (18)	C13—C12—H12A	120.1
C6—C1—C2	117.47 (12)	C11—C12—H12A	120.1
C6—C1—C7	123.07 (12)	O3—C13—C12	124.72 (12)
C2—C1—C7	119.46 (11)	O3—C13—C14	115.69 (12)
C3—C2—C1	121.63 (12)	C12—C13—C14	119.59 (12)
C3—C2—H2A	119.2	C15—C14—O4	119.17 (12)
C1—C2—H2A	119.2	C15—C14—C13	119.88 (12)
C2—C3—C4	120.24 (12)	O4—C14—C13	120.72 (12)
C2—C3—H3A	119.9	C14—C15—C10	122.04 (12)
C4—C3—H3A	119.9	C14—C15—H15A	119.0
N1—C4—C5	120.65 (12)	C10—C15—H15A	119.0
N1—C4—C3	120.86 (12)	O2—C16—H16A	109.5
C5—C4—C3	118.44 (12)	O2—C16—H16B	109.5
C6—C5—C4	120.69 (12)	H16A—C16—H16B	109.5
C6—C5—H5A	119.7	O2—C16—H16C	109.5
C4—C5—H5A	119.7	H16A—C16—H16C	109.5
C5—C6—C1	121.26 (12)	H16B—C16—H16C	109.5
C5—C6—H6A	119.4	O3—C17—H17A	109.5
C1—C6—H6A	119.4	O3—C17—H17B	109.5
O1—C7—C8	120.93 (12)	H17A—C17—H17B	109.5
O1—C7—C1	120.63 (12)	O3—C17—H17C	109.5
C8—C7—C1	118.43 (11)	H17A—C17—H17C	109.5
C9—C8—C7	122.45 (12)	H17B—C17—H17C	109.5
C9—C8—H8A	118.8	O4—C18—H18A	109.5
C7—C8—H8A	118.8	O4—C18—H18B	109.5
C8—C9—C10	125.73 (12)	H18A—C18—H18B	109.5
C8—C9—H9A	117.1	O4—C18—H18C	109.5
C10—C9—H9A	117.1	H18A—C18—H18C	109.5
C15—C10—C11	117.31 (12)	H18B—C18—H18C	109.5
C15—C10—C9	121.64 (12)
C6—C1—C2—C3	−2.81 (19)	C15—C10—C11—O2	179.96 (11)
C7—C1—C2—C3	176.14 (12)	C9—C10—C11—O2	−1.95 (18)
C1—C2—C3—C4	−1.5 (2)	C15—C10—C11—C12	0.21 (19)
C2—C3—C4—N1	−172.31 (13)	C9—C10—C11—C12	178.30 (12)
C2—C3—C4—C5	5.09 (19)	O2—C11—C12—C13	−179.69 (12)
N1—C4—C5—C6	173.09 (13)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—C6	−4.31 (19)	C17—O3—C13—C12	1.5 (2)
C4—C5—C6—C1	−0.1 (2)	C17—O3—C13—C14	−178.72 (12)
C2—C1—C6—C5	3.6 (2)	C11—C12—C13—O3	179.60 (13)
C7—C1—C6—C5	−175.30 (13)	C11—C12—C13—C14	−0.2 (2)
C6—C1—C7—O1	−170.62 (13)	C18—O4—C14—C15	104.12 (16)
C2—C1—C7—O1	10.5 (2)	C18—O4—C14—C13	−81.36 (17)
C6—C1—C7—C8	10.37 (19)	O3—C13—C14—C15	−179.72 (12)
C2—C1—C7—C8	−168.52 (12)	C12—C13—C14—C15	0.1 (2)
O1—C7—C8—C9	−1.0 (2)	O3—C13—C14—O4	5.79 (19)
C1—C7—C8—C9	177.98 (13)	C12—C13—C14—O4	−174.38 (12)
C7—C8—C9—C10	177.99 (13)	O4—C14—C15—C10	174.73 (12)
C8—C9—C10—C15	−7.9 (2)	C13—C14—C15—C10	0.2 (2)
C8—C9—C10—C11	174.10 (14)	C11—C10—C15—C14	−0.3 (2)
C16—O2—C11—C12	−1.45 (19)	C9—C10—C15—C14	−178.39 (13)
C16—O2—C11—C10	178.80 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1···O1ii	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1⋯O1ii	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)

Symmetry codes: (i) ; (ii) .