1-(4-Amino­phenyl)-3-(3,4-di­methoxy­phenyl)­prop-2-en-1-one

In the title mol­ecule, C₁₇H₁₇NO₃, the configuration of the keto group with respect to the olefinic double bond is s-cis. The dihedral angle between the two aromatic rings is 9.5 (2)°. Both the H atoms of the amino group are involved in N—H...O hydrogen bonding to form molecular layers parallel to the (100) plane. The layers are stacked along the b axis and are interlinked by C—H...π and C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.088
• wR factor = 0.217
• Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); 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).

1-(4-Aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H17NO3	F(000) = 1200
Mr = 283.32	Dx = 1.254 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2797 reflections
a = 13.856 (2) Å	θ = 2.7–28.3°
b = 8.8243 (13) Å	µ = 0.09 mm^−1
c = 24.775 (4) Å	T = 293 K
β = 97.630 (3)°	Block, yellow
V = 3002.4 (8) Å^3	0.44 × 0.40 × 0.36 mm
Z = 8

Data collection

Siemens SMART CCD area detector diffractometer	1787 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
Detector resolution: 8.33 pixels mm^-1	h = −15→16
ω scans	k = −10→9
7214 measured reflections	l = −29→21
2644 independent 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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.217	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + 6.2455P] where P = (Fo^2 + 2Fc^2)/3
2644 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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	0.6031 (2)	0.1991 (3)	0.37057 (11)	0.0608 (9)
O2	0.6500 (2)	−0.0253 (3)	0.70317 (10)	0.0566 (8)
O3	0.6651 (2)	0.2582 (3)	0.67891 (11)	0.0560 (8)
N1	0.5904 (3)	0.8983 (4)	0.31407 (15)	0.0681 (12)
H1A	0.5882	0.9771	0.3343	0.082*
H1B	0.5899	0.9086	0.2795	0.082*
C1	0.6243 (3)	−0.0526 (5)	0.55399 (17)	0.0570 (12)
H1	0.6159	−0.1253	0.5266	0.068*
C2	0.6308 (3)	−0.0983 (5)	0.60781 (17)	0.0558 (11)
H2	0.6267	−0.2006	0.6162	0.067*
C3	0.6433 (3)	0.0073 (4)	0.64898 (15)	0.0448 (10)
C4	0.6513 (3)	0.1619 (4)	0.63576 (15)	0.0423 (9)
C5	0.6442 (3)	0.2044 (4)	0.58216 (15)	0.0434 (10)
H5	0.6489	0.3066	0.5736	0.052*
C6	0.6301 (3)	0.0979 (5)	0.54006 (15)	0.0461 (10)
C7	0.6200 (3)	0.1438 (5)	0.48270 (16)	0.0526 (11)
H7	0.6118	0.0649	0.4576	0.063*
C8	0.6208 (3)	0.2798 (5)	0.46176 (16)	0.0506 (11)
H8	0.6292	0.3627	0.4851	0.061*
C9	0.6089 (3)	0.3067 (5)	0.40249 (15)	0.0459 (10)
C10	0.6036 (3)	0.4634 (4)	0.38174 (14)	0.0424 (9)
C11	0.6006 (3)	0.5926 (5)	0.41418 (15)	0.0542 (11)
H11	0.6021	0.5813	0.4516	0.065*
C12	0.5954 (4)	0.7353 (5)	0.39220 (17)	0.0602 (12)
H12	0.5925	0.8186	0.4149	0.072*
C13	0.5945 (3)	0.7582 (5)	0.33658 (16)	0.0465 (10)
C14	0.5980 (3)	0.6293 (5)	0.30375 (15)	0.0533 (11)
H14	0.5974	0.6402	0.2664	0.064*
C15	0.6024 (3)	0.4885 (5)	0.32620 (15)	0.0514 (11)
H15	0.6047	0.4052	0.3034	0.062*
C16	0.6392 (4)	−0.1797 (5)	0.71765 (18)	0.0704 (15)
H16A	0.6411	−0.1877	0.7564	0.106*
H16B	0.6912	−0.2383	0.7062	0.106*
H16C	0.5779	−0.2172	0.7001	0.106*
C17	0.6724 (4)	0.4159 (4)	0.66698 (18)	0.0624 (13)
H17A	0.6861	0.4718	0.7004	0.094*
H17B	0.6120	0.4505	0.6473	0.094*
H17C	0.7240	0.4314	0.6452	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.090 (2)	0.0531 (18)	0.0403 (16)	−0.0064 (16)	0.0119 (14)	−0.0078 (14)
O2	0.079 (2)	0.0521 (18)	0.0380 (16)	−0.0025 (15)	0.0055 (14)	0.0062 (13)
O3	0.081 (2)	0.0455 (17)	0.0413 (16)	−0.0034 (14)	0.0088 (14)	−0.0020 (13)
N1	0.099 (3)	0.053 (2)	0.054 (2)	−0.003 (2)	0.013 (2)	0.0030 (18)
C1	0.075 (3)	0.052 (3)	0.044 (2)	−0.009 (2)	0.006 (2)	−0.008 (2)
C2	0.070 (3)	0.043 (2)	0.054 (3)	−0.005 (2)	0.008 (2)	0.006 (2)
C3	0.044 (2)	0.048 (2)	0.043 (2)	0.0007 (18)	0.0083 (17)	0.0024 (19)
C4	0.043 (2)	0.046 (2)	0.038 (2)	−0.0019 (18)	0.0070 (16)	−0.0045 (17)
C5	0.047 (2)	0.042 (2)	0.042 (2)	−0.0017 (18)	0.0074 (17)	0.0072 (17)
C6	0.046 (2)	0.052 (3)	0.040 (2)	−0.0033 (19)	0.0051 (17)	−0.0010 (18)
C7	0.057 (3)	0.060 (3)	0.040 (2)	−0.009 (2)	0.0076 (19)	−0.009 (2)
C8	0.058 (3)	0.052 (3)	0.041 (2)	−0.004 (2)	0.0056 (19)	−0.0027 (19)
C9	0.045 (2)	0.057 (3)	0.036 (2)	−0.0027 (19)	0.0059 (17)	−0.0050 (19)
C10	0.041 (2)	0.055 (2)	0.031 (2)	0.0021 (18)	0.0059 (16)	−0.0079 (17)
C11	0.073 (3)	0.063 (3)	0.027 (2)	0.008 (2)	0.0064 (18)	−0.0032 (19)
C12	0.080 (3)	0.053 (3)	0.047 (3)	0.001 (2)	0.007 (2)	−0.012 (2)
C13	0.042 (2)	0.053 (3)	0.045 (2)	0.0012 (18)	0.0058 (17)	0.0037 (19)
C14	0.064 (3)	0.065 (3)	0.032 (2)	−0.001 (2)	0.0077 (19)	0.002 (2)
C15	0.066 (3)	0.051 (3)	0.038 (2)	0.003 (2)	0.0109 (19)	−0.0100 (19)
C16	0.106 (4)	0.052 (3)	0.052 (3)	−0.011 (3)	0.003 (3)	0.015 (2)
C17	0.086 (4)	0.045 (3)	0.056 (3)	−0.008 (2)	0.012 (2)	−0.008 (2)

Geometric parameters (Å, º)

O1—C9	1.231 (4)	C8—C9	1.475 (5)
O2—C3	1.364 (4)	C8—H8	0.93
O2—C16	1.421 (5)	C9—C10	1.474 (5)
O3—C4	1.359 (4)	C10—C15	1.392 (5)
O3—C17	1.429 (5)	C10—C11	1.399 (5)
N1—C13	1.355 (5)	C11—C12	1.370 (6)
N1—H1A	0.86	C11—H11	0.93
N1—H1B	0.86	C12—C13	1.391 (6)
C1—C6	1.377 (6)	C12—H12	0.93
C1—C2	1.384 (6)	C13—C14	1.403 (6)
C1—H1	0.93	C14—C15	1.359 (5)
C2—C3	1.375 (6)	C14—H14	0.93
C2—H2	0.93	C15—H15	0.93
C3—C4	1.410 (5)	C16—H16A	0.96
C4—C5	1.371 (5)	C16—H16B	0.96
C5—C6	1.399 (5)	C16—H16C	0.96
C5—H5	0.93	C17—H17A	0.96
C6—C7	1.466 (5)	C17—H17B	0.96
C7—C8	1.308 (5)	C17—H17C	0.96
C7—H7	0.93
C3—O2—C16	117.1 (3)	C10—C9—C8	119.5 (3)
C4—O3—C17	116.9 (3)	C15—C10—C11	116.2 (4)
C13—N1—H1A	120.0	C15—C10—C9	119.2 (3)
C13—N1—H1B	120.0	C11—C10—C9	124.6 (3)
H1A—N1—H1B	120.0	C12—C11—C10	121.6 (4)
C6—C1—C2	121.6 (4)	C12—C11—H11	119.2
C6—C1—H1	119.2	C10—C11—H11	119.2
C2—C1—H1	119.2	C11—C12—C13	121.4 (4)
C3—C2—C1	120.2 (4)	C11—C12—H12	119.3
C3—C2—H2	119.9	C13—C12—H12	119.3
C1—C2—H2	119.9	N1—C13—C12	122.3 (4)
O2—C3—C2	124.9 (4)	N1—C13—C14	120.3 (4)
O2—C3—C4	115.8 (3)	C12—C13—C14	117.4 (4)
C2—C3—C4	119.3 (4)	C15—C14—C13	120.5 (4)
O3—C4—C5	125.1 (4)	C15—C14—H14	119.8
O3—C4—C3	115.4 (3)	C13—C14—H14	119.8
C5—C4—C3	119.5 (4)	C14—C15—C10	123.0 (4)
C4—C5—C6	121.5 (4)	C14—C15—H15	118.5
C4—C5—H5	119.2	C10—C15—H15	118.5
C6—C5—H5	119.2	O2—C16—H16A	109.5
C1—C6—C5	117.9 (4)	O2—C16—H16B	109.5
C1—C6—C7	120.5 (4)	H16A—C16—H16B	109.5
C5—C6—C7	121.5 (4)	O2—C16—H16C	109.5
C8—C7—C6	129.3 (4)	H16A—C16—H16C	109.5
C8—C7—H7	115.4	H16B—C16—H16C	109.5
C6—C7—H7	115.4	O3—C17—H17A	109.5
C7—C8—C9	122.5 (4)	O3—C17—H17B	109.5
C7—C8—H8	118.8	H17A—C17—H17B	109.5
C9—C8—H8	118.8	O3—C17—H17C	109.5
O1—C9—C10	120.2 (3)	H17A—C17—H17C	109.5
O1—C9—C8	120.3 (4)	H17B—C17—H17C	109.5
C6—C1—C2—C3	0.0 (7)	C5—C6—C7—C8	−0.9 (7)
C16—O2—C3—C2	−2.7 (6)	C6—C7—C8—C9	−179.6 (4)
C16—O2—C3—C4	178.1 (4)	C7—C8—C9—O1	−4.0 (6)
C1—C2—C3—O2	179.6 (4)	C7—C8—C9—C10	175.7 (4)
C1—C2—C3—C4	−1.2 (6)	O1—C9—C10—C15	−6.8 (6)
C17—O3—C4—C5	0.1 (6)	C8—C9—C10—C15	173.5 (4)
C17—O3—C4—C3	−179.3 (4)	O1—C9—C10—C11	173.9 (4)
O2—C3—C4—O3	0.3 (5)	C8—C9—C10—C11	−5.8 (6)
C2—C3—C4—O3	−179.0 (4)	C15—C10—C11—C12	0.8 (6)
O2—C3—C4—C5	−179.2 (3)	C9—C10—C11—C12	−179.8 (4)
C2—C3—C4—C5	1.5 (6)	C10—C11—C12—C13	−1.0 (7)
O3—C4—C5—C6	179.9 (4)	C11—C12—C13—N1	−179.4 (4)
C3—C4—C5—C6	−0.6 (6)	C11—C12—C13—C14	0.6 (7)
C2—C1—C6—C5	0.9 (7)	N1—C13—C14—C15	179.8 (4)
C2—C1—C6—C7	−178.1 (4)	C12—C13—C14—C15	−0.2 (6)
C4—C5—C6—C1	−0.5 (6)	C13—C14—C15—C10	0.0 (7)
C4—C5—C6—C7	178.4 (4)	C11—C10—C15—C14	−0.4 (6)
C1—C6—C7—C8	178.0 (5)	C9—C10—C15—C14	−179.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.15	2.995 (5)	166
N1—H1B···O2^ii	0.86	2.40	3.176 (5)	151
C7—H7···O1	0.93	2.45	2.799 (5)	102
C15—H15···O1	0.93	2.47	2.780 (5)	100
C14—H14···O3^ii	0.93	2.63	3.490 (5)	154
C16—H16A···O1^iii	0.96	2.95	3.891 (5)	168
C16—H16A···O3^iv	0.96	2.98	3.518 (6)	117
C16—H16C···O1^v	0.96	2.87	3.758 (6)	155
C17—H17C···O1^vi	0.96	2.73	3.513 (6)	139
C17—H17B···Cg1^vii	0.96	2.96	3.739 (6)	139

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z−1/2; (iii) x, −y, z+1/2; (iv) −x+3/2, y−1/2, −z+3/2; (v) −x+1, −y, −z+1; (vi) −x+3/2, −y+1/2, −z+1; (vii) −x+1, −y+1, −z+1.