(Z)-3-(2-Amino-anilino)-1-phenyl-but-2-en-1-one.

In the title compound, C16H16N2O, the phenyl and 2-amino-phenyl rings are almost perpendicular to one another, with a dihedral angle of 82.77 (8)°. There is an intra-molecular N-H⋯O hydrogen bond in the mol-ecule. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds forming chains along [001]. There are also C-H⋯π inter-actions present, linking the chains to form a three-dimensional structure.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Lin et al. (2002 ▶). For a related chalcone structure, see: Ranjith et al. (2010 ▶).

Experimental

Crystal data

C16H16N2O

M = 252.31

Monoclinic,

a = 15.489 (5) Å

b = 16.422 (5) Å

c = 11.684 (5) Å

β = 110.646 (5)°

V = 2781.1 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.977, T max = 0.985

18172 measured reflections

4023 independent reflections

2805 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.152

S = 1.01

4023 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301060X/su2583sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301060X/su2583Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301060X/su2583Isup3.cml

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

C16H16N2O	F(000) = 1072
Mr = 252.31	Dx = 1.205 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4023 reflections
a = 15.489 (5) Å	θ = 2.3–30.0°
b = 16.422 (5) Å	µ = 0.08 mm−1
c = 11.684 (5) Å	T = 293 K
β = 110.646 (5)°	Block, colourless
V = 2781.1 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	4023 independent reflections
Radiation source: fine-focus sealed tube	2805 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −21→21
Tmin = 0.977, Tmax = 0.985	k = −23→21
18172 measured reflections	l = −16→16

Refinement on F2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.050	Secondary atom site location: difference Fourier map
wR(F2) = 0.152	Hydrogen site location: inferred from neighbouring sites
S = 1.01	H-atom parameters constrained
4023 reflections	w = 1/[σ2(Fo2) + (0.0752P)2 + 0.9814P] where P = (Fo2 + 2Fc2)/3
173 parameters	(Δ/σ)max = 0.001

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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	0.95043 (6)	0.11163 (6)	0.08924 (9)	0.0464 (3)
N1	0.88576 (8)	0.00321 (8)	0.37211 (13)	0.0637 (5)
N2	0.81921 (7)	0.11567 (7)	0.18340 (10)	0.0392 (3)
C1	0.79279 (8)	0.01569 (8)	0.31971 (12)	0.0410 (4)
C2	0.73017 (10)	−0.02773 (9)	0.35822 (14)	0.0490 (4)
C3	0.63692 (10)	−0.01773 (9)	0.30190 (15)	0.0527 (5)
C4	0.60208 (9)	0.03447 (10)	0.20489 (15)	0.0546 (5)
C5	0.66227 (9)	0.07806 (9)	0.16509 (13)	0.0470 (4)
C6	0.75672 (8)	0.07045 (8)	0.22326 (11)	0.0375 (3)
C7	0.82154 (8)	0.19629 (8)	0.17067 (10)	0.0356 (3)
C8	0.75857 (10)	0.24833 (9)	0.21128 (14)	0.0472 (4)
C9	0.88265 (8)	0.23183 (8)	0.12356 (11)	0.0383 (4)
C10	0.94545 (8)	0.18800 (8)	0.08424 (10)	0.0362 (3)
C11	1.00769 (9)	0.23272 (8)	0.03291 (11)	0.0407 (4)
C12	1.03522 (9)	0.31218 (9)	0.06381 (13)	0.0464 (4)
C13	1.09525 (11)	0.35058 (10)	0.01689 (16)	0.0580 (5)
C14	1.12735 (13)	0.30984 (12)	−0.06213 (17)	0.0672 (7)
C15	1.10050 (14)	0.23138 (13)	−0.09387 (18)	0.0786 (8)
C16	1.04137 (12)	0.19230 (11)	−0.04670 (15)	0.0624 (6)
H1A	0.92310	0.02930	0.34570	0.0760*
H1B	0.90690	−0.03080	0.43150	0.0760*
H2	0.75230	−0.06400	0.42320	0.0590*
H2A	0.85990	0.08800	0.16560	0.0470*
H3	0.59670	−0.04670	0.32980	0.0630*
H4	0.53870	0.04040	0.16640	0.0650*
H5	0.63910	0.11290	0.09850	0.0560*
H8A	0.69690	0.24440	0.15290	0.0710*
H8B	0.77890	0.30390	0.21730	0.0710*
H8C	0.75950	0.23010	0.28970	0.0710*
H9	0.88240	0.28830	0.11740	0.0460*
H12	1.01320	0.34040	0.11690	0.0560*
H13	1.11370	0.40400	0.03910	0.0700*
H14	1.16730	0.33550	−0.09410	0.0810*
H15	1.12220	0.20390	−0.14790	0.0940*
H16	1.02410	0.13860	−0.06850	0.0750*

	U11	U22	U33	U12	U13	U23
O1	0.0449 (5)	0.0420 (5)	0.0611 (6)	0.0004 (4)	0.0298 (4)	−0.0034 (4)
N1	0.0373 (6)	0.0634 (9)	0.0840 (10)	0.0005 (5)	0.0135 (6)	0.0327 (7)
N2	0.0351 (5)	0.0400 (6)	0.0495 (6)	0.0026 (4)	0.0237 (4)	0.0041 (4)
C1	0.0375 (6)	0.0356 (7)	0.0518 (7)	−0.0017 (5)	0.0182 (5)	0.0021 (5)
C2	0.0513 (8)	0.0400 (7)	0.0604 (8)	−0.0043 (6)	0.0255 (6)	0.0080 (6)
C3	0.0473 (7)	0.0468 (8)	0.0748 (10)	−0.0095 (6)	0.0348 (7)	0.0005 (7)
C4	0.0337 (6)	0.0576 (9)	0.0748 (10)	−0.0036 (6)	0.0221 (6)	−0.0007 (7)
C5	0.0369 (6)	0.0525 (8)	0.0519 (7)	0.0013 (6)	0.0160 (6)	0.0046 (6)
C6	0.0348 (6)	0.0377 (6)	0.0448 (6)	−0.0015 (5)	0.0201 (5)	−0.0002 (5)
C7	0.0333 (5)	0.0413 (7)	0.0335 (5)	0.0019 (5)	0.0133 (4)	0.0015 (5)
C8	0.0465 (7)	0.0465 (8)	0.0581 (8)	0.0027 (6)	0.0304 (6)	−0.0030 (6)
C9	0.0404 (6)	0.0371 (7)	0.0422 (6)	0.0013 (5)	0.0207 (5)	0.0033 (5)
C10	0.0337 (5)	0.0422 (7)	0.0343 (5)	−0.0008 (5)	0.0139 (4)	0.0005 (5)
C11	0.0378 (6)	0.0504 (8)	0.0382 (6)	0.0014 (5)	0.0186 (5)	0.0048 (5)
C12	0.0467 (7)	0.0474 (8)	0.0512 (7)	0.0013 (6)	0.0250 (6)	0.0055 (6)
C13	0.0572 (9)	0.0535 (9)	0.0714 (10)	−0.0037 (7)	0.0326 (8)	0.0115 (7)
C14	0.0705 (11)	0.0736 (12)	0.0761 (11)	−0.0036 (9)	0.0490 (9)	0.0162 (9)
C15	0.0961 (14)	0.0872 (14)	0.0837 (12)	−0.0094 (11)	0.0705 (12)	−0.0065 (10)
C16	0.0758 (11)	0.0638 (10)	0.0667 (10)	−0.0100 (8)	0.0487 (9)	−0.0088 (8)

O1—C10	1.2566 (17)	C11—C12	1.381 (2)
N1—C1	1.367 (2)	C12—C13	1.386 (2)
N2—C6	1.4224 (18)	C13—C14	1.368 (3)
N2—C7	1.3342 (18)	C14—C15	1.365 (3)
N1—H1A	0.8600	C15—C16	1.382 (3)
N1—H1B	0.8600	C2—H2	0.9300
N2—H2A	0.8600	C3—H3	0.9300
C1—C2	1.400 (2)	C4—H4	0.9300
C1—C6	1.3953 (19)	C5—H5	0.9300
C2—C3	1.370 (2)	C8—H8A	0.9600
C3—C4	1.371 (2)	C8—H8B	0.9600
C4—C5	1.380 (2)	C8—H8C	0.9600
C5—C6	1.384 (2)	C9—H9	0.9300
C7—C8	1.494 (2)	C12—H12	0.9300
C7—C9	1.3809 (19)	C13—H13	0.9300
C9—C10	1.4108 (19)	C14—H14	0.9300
C10—C11	1.495 (2)	C15—H15	0.9300
C11—C16	1.386 (2)	C16—H16	0.9300
C6—N2—C7	127.08 (12)	C14—C15—C16	120.76 (19)
C1—N1—H1A	120.00	C11—C16—C15	120.30 (17)
C1—N1—H1B	120.00	C1—C2—H2	119.00
H1A—N1—H1B	120.00	C3—C2—H2	119.00
C7—N2—H2A	117.00	C2—C3—H3	120.00
C6—N2—H2A	116.00	C4—C3—H3	120.00
N1—C1—C6	121.13 (12)	C3—C4—H4	120.00
C2—C1—C6	117.54 (13)	C5—C4—H4	120.00
N1—C1—C2	121.30 (13)	C4—C5—H5	120.00
C1—C2—C3	121.15 (14)	C6—C5—H5	120.00
C2—C3—C4	120.88 (15)	C7—C8—H8A	109.00
C3—C4—C5	119.16 (14)	C7—C8—H8B	109.00
C4—C5—C6	120.69 (13)	C7—C8—H8C	109.00
N2—C6—C5	121.03 (12)	H8A—C8—H8B	110.00
C1—C6—C5	120.50 (12)	H8A—C8—H8C	109.00
N2—C6—C1	118.43 (12)	H8B—C8—H8C	109.00
N2—C7—C8	119.06 (12)	C7—C9—H9	118.00
N2—C7—C9	120.87 (12)	C10—C9—H9	118.00
C8—C7—C9	120.05 (12)	C11—C12—H12	120.00
C7—C9—C10	124.22 (12)	C13—C12—H12	119.00
C9—C10—C11	119.74 (12)	C12—C13—H13	120.00
O1—C10—C11	118.11 (12)	C14—C13—H13	120.00
O1—C10—C9	122.15 (12)	C13—C14—H14	120.00
C10—C11—C12	122.86 (12)	C15—C14—H14	120.00
C12—C11—C16	118.27 (14)	C14—C15—H15	120.00
C10—C11—C16	118.85 (13)	C16—C15—H15	120.00
C11—C12—C13	120.99 (14)	C11—C16—H16	120.00
C12—C13—C14	119.90 (16)	C15—C16—H16	120.00
C13—C14—C15	119.79 (19)
C6—N2—C7—C9	−175.89 (12)	C8—C7—C9—C10	179.21 (12)
C7—N2—C6—C1	−127.15 (14)	C7—C9—C10—O1	0.06 (19)
C7—N2—C6—C5	55.26 (18)	C7—C9—C10—C11	179.11 (11)
C6—N2—C7—C8	5.71 (19)	O1—C10—C11—C12	−154.23 (13)
C6—C1—C2—C3	1.0 (2)	O1—C10—C11—C16	24.03 (18)
N1—C1—C6—N2	−2.42 (19)	C9—C10—C11—C12	26.69 (18)
N1—C1—C6—C5	175.19 (13)	C9—C10—C11—C16	−155.06 (13)
N1—C1—C2—C3	−177.06 (14)	C10—C11—C12—C13	178.04 (14)
C2—C1—C6—N2	179.49 (12)	C16—C11—C12—C13	−0.2 (2)
C2—C1—C6—C5	−2.9 (2)	C10—C11—C16—C15	−178.72 (15)
C1—C2—C3—C4	0.8 (2)	C12—C11—C16—C15	−0.4 (2)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—C14	0.6 (2)
C3—C4—C5—C6	−1.1 (2)	C12—C13—C14—C15	−0.4 (3)
C4—C5—C6—N2	−179.49 (13)	C13—C14—C15—C16	−0.3 (3)
C4—C5—C6—C1	3.0 (2)	C14—C15—C16—C11	0.6 (3)
N2—C7—C9—C10	0.83 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.95	2.6311 (19)	135
N1—H1A···O1i	0.86	2.28	3.001 (2)	142
N1—H1B···O1ii	0.86	2.18	3.034 (2)	174
C14—H14···Cg1iii	0.93	2.96	3.773 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of ring C1–C6.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.95	2.6311 (19)	135
N1—H1A⋯O1i	0.86	2.28	3.001 (2)	142
N1—H1B⋯O1ii	0.86	2.18	3.034 (2)	174
C14—H14⋯Cg1iii	0.93	2.96	3.773 (3)	147

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