(Z)-3-[(2-Amino-benz-yl)amino]-1-phenyl-but-2-en-1-one.

In the title compound, C17H18N2O, the aromatic rings are almost normal to one another, making a dihedral angle of 89.00 (8)°. There is an intra-molecular N-H⋯O hydrogen bond in the mol-ecule enclosing an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along [010].

Related literature

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

Experimental

Crystal data

C17H18N2O

M = 266.33

Monoclinic,

a = 11.3197 (4) Å

b = 9.8341 (3) Å

c = 13.4207 (4) Å

β = 106.387 (2)°

V = 1433.29 (8) Å3

Z = 4

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 = 0.698, T max = 0.746

14860 measured reflections

3921 independent reflections

2528 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.156

S = 1.03

3921 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012070/su2735sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012070/su2735Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012070/su2735Isup3.cml

CCDC reference: 1005094

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H18N2O	F(000) = 568
Mr = 266.33	Dx = 1.234 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3921 reflections
a = 11.3197 (4) Å	θ = 1.9–29.3°
b = 9.8341 (3) Å	µ = 0.08 mm−1
c = 13.4207 (4) Å	T = 293 K
β = 106.387 (2)°	Block, colourless
V = 1433.29 (8) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3921 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 29.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.698, Tmax = 0.746	k = −13→13
14860 measured reflections	l = −10→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0715P)2 + 0.2241P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3921 reflections	Δρmax = 0.23 e Å−3
183 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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
C1	0.37143 (13)	0.36601 (14)	−0.34891 (10)	0.0447 (3)
C2	0.24361 (15)	0.37189 (17)	−0.38045 (13)	0.0588 (4)
H2	0.2035	0.4073	−0.4455	0.071*
C3	0.17631 (16)	0.3268 (2)	−0.31782 (17)	0.0701 (5)
H3	0.0908	0.3311	−0.3407	0.084*
C4	0.23319 (19)	0.27475 (19)	−0.22096 (17)	0.0724 (5)
H4	0.1867	0.2442	−0.1783	0.087*
C5	0.36069 (17)	0.26853 (18)	−0.18788 (13)	0.0601 (4)
H5	0.3995	0.2335	−0.1224	0.072*
C6	0.43142 (13)	0.31337 (15)	−0.25025 (10)	0.0445 (3)
C7	0.56975 (14)	0.3028 (2)	−0.21832 (11)	0.0602 (4)
H7A	0.5930	0.2264	−0.2545	0.072*
H7B	0.6031	0.3844	−0.2407	0.072*
C8	0.66303 (14)	0.38414 (16)	−0.03882 (11)	0.0516 (4)
C9	0.6376 (2)	0.5280 (2)	−0.07480 (15)	0.0830 (6)
H9A	0.6843	0.5498	−0.1222	0.125*
H9B	0.6607	0.5880	−0.0161	0.125*
H9C	0.5513	0.5384	−0.1092	0.125*
C10	0.72605 (14)	0.35770 (15)	0.06411 (11)	0.0492 (4)
H10	0.7488	0.4313	0.1090	0.059*
C11	0.75754 (13)	0.22683 (14)	0.10462 (10)	0.0438 (3)
C12	0.83849 (12)	0.20920 (14)	0.21386 (10)	0.0414 (3)
C13	0.88339 (15)	0.08133 (17)	0.24592 (12)	0.0559 (4)
H13	0.8632	0.0086	0.1999	0.067*
C14	0.95824 (18)	0.0598 (2)	0.34596 (13)	0.0714 (5)
H14	0.9888	−0.0267	0.3663	0.086*
C15	0.98725 (17)	0.1654 (2)	0.41484 (12)	0.0709 (5)
H15	1.0376	0.1509	0.4819	0.085*
C16	0.94187 (17)	0.2926 (2)	0.38466 (12)	0.0691 (5)
H16	0.9604	0.3641	0.4318	0.083*
C17	0.86870 (15)	0.31536 (17)	0.28458 (11)	0.0568 (4)
H17	0.8395	0.4025	0.2645	0.068*
N1	0.43740 (14)	0.41274 (17)	−0.41456 (10)	0.0704 (4)
H1A	0.3993	0.4452	−0.4745	0.084*
H1B	0.5165	0.4093	−0.3954	0.084*
N2	0.62611 (13)	0.28532 (14)	−0.10721 (9)	0.0572 (4)
H2A	0.6362	0.2033	−0.0841	0.069*
O1	0.72160 (13)	0.12117 (11)	0.05299 (8)	0.0710 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0496 (8)	0.0388 (8)	0.0424 (7)	0.0033 (6)	0.0076 (6)	−0.0008 (5)
C2	0.0501 (9)	0.0528 (9)	0.0654 (9)	0.0066 (7)	0.0031 (7)	−0.0081 (7)
C3	0.0493 (9)	0.0607 (11)	0.0986 (14)	−0.0023 (8)	0.0179 (9)	−0.0194 (10)
C4	0.0741 (12)	0.0607 (11)	0.0985 (14)	−0.0168 (9)	0.0506 (11)	−0.0133 (10)
C5	0.0728 (11)	0.0578 (10)	0.0551 (8)	−0.0043 (8)	0.0270 (8)	0.0019 (7)
C6	0.0493 (8)	0.0446 (8)	0.0381 (6)	0.0003 (6)	0.0101 (5)	0.0000 (6)
C7	0.0511 (8)	0.0879 (13)	0.0373 (7)	0.0072 (8)	0.0052 (6)	0.0062 (7)
C8	0.0517 (8)	0.0490 (9)	0.0492 (7)	0.0033 (7)	0.0065 (6)	0.0074 (6)
C9	0.1066 (16)	0.0575 (12)	0.0705 (11)	0.0052 (11)	0.0013 (11)	0.0193 (9)
C10	0.0554 (8)	0.0400 (8)	0.0446 (7)	−0.0008 (6)	0.0016 (6)	0.0002 (6)
C11	0.0445 (7)	0.0414 (8)	0.0402 (6)	−0.0044 (6)	0.0032 (5)	−0.0026 (5)
C12	0.0389 (7)	0.0425 (8)	0.0401 (6)	−0.0038 (5)	0.0069 (5)	0.0023 (5)
C13	0.0635 (10)	0.0474 (9)	0.0527 (8)	0.0000 (7)	0.0094 (7)	0.0081 (7)
C14	0.0772 (12)	0.0672 (12)	0.0623 (10)	0.0094 (9)	0.0074 (9)	0.0260 (9)
C15	0.0655 (11)	0.0922 (14)	0.0453 (8)	−0.0024 (10)	0.0001 (7)	0.0165 (9)
C16	0.0724 (11)	0.0783 (13)	0.0455 (8)	−0.0077 (10)	−0.0015 (8)	−0.0074 (8)
C17	0.0621 (9)	0.0502 (9)	0.0482 (8)	−0.0006 (7)	−0.0008 (7)	−0.0032 (7)
N1	0.0644 (9)	0.0951 (12)	0.0499 (7)	0.0127 (8)	0.0134 (6)	0.0302 (7)
N2	0.0638 (8)	0.0585 (8)	0.0395 (6)	0.0052 (6)	−0.0012 (6)	0.0044 (5)
O1	0.0959 (9)	0.0427 (7)	0.0538 (6)	−0.0044 (6)	−0.0122 (6)	−0.0065 (5)

C1—N1	1.384 (2)	C9—H9C	0.9600
C1—C2	1.389 (2)	C10—C11	1.403 (2)
C1—C6	1.4053 (18)	C10—H10	0.9300
C2—C3	1.358 (3)	C11—O1	1.2516 (16)
C2—H2	0.9300	C11—C12	1.5036 (17)
C3—C4	1.376 (3)	C12—C13	1.379 (2)
C3—H3	0.9300	C12—C17	1.387 (2)
C4—C5	1.386 (3)	C13—C14	1.387 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (2)	C14—C15	1.367 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.506 (2)	C15—C16	1.369 (3)
C7—N2	1.4571 (17)	C15—H15	0.9300
C7—H7A	0.9700	C16—C17	1.383 (2)
C7—H7B	0.9700	C16—H16	0.9300
C8—N2	1.3210 (19)	C17—H17	0.9300
C8—C10	1.3888 (19)	N1—H1A	0.8600
C8—C9	1.496 (2)	N1—H1B	0.8600
C9—H9A	0.9600	N2—H2A	0.8600
C9—H9B	0.9600
N1—C1—C2	119.65 (13)	H9B—C9—H9C	109.5
N1—C1—C6	121.19 (13)	C8—C10—C11	124.07 (13)
C2—C1—C6	119.16 (14)	C8—C10—H10	118.0
C3—C2—C1	121.04 (16)	C11—C10—H10	118.0
C3—C2—H2	119.5	O1—C11—C10	122.65 (12)
C1—C2—H2	119.5	O1—C11—C12	117.23 (12)
C2—C3—C4	120.75 (16)	C10—C11—C12	120.12 (12)
C2—C3—H3	119.6	C13—C12—C17	118.34 (13)
C4—C3—H3	119.6	C13—C12—C11	118.62 (13)
C3—C4—C5	119.09 (16)	C17—C12—C11	123.03 (13)
C3—C4—H4	120.5	C12—C13—C14	120.79 (16)
C5—C4—H4	120.5	C12—C13—H13	119.6
C6—C5—C4	121.33 (16)	C14—C13—H13	119.6
C6—C5—H5	119.3	C15—C14—C13	120.23 (17)
C4—C5—H5	119.3	C15—C14—H14	119.9
C5—C6—C1	118.63 (14)	C13—C14—H14	119.9
C5—C6—C7	122.58 (13)	C14—C15—C16	119.68 (15)
C1—C6—C7	118.75 (12)	C14—C15—H15	120.2
N2—C7—C6	114.79 (13)	C16—C15—H15	120.2
N2—C7—H7A	108.6	C15—C16—C17	120.48 (16)
C6—C7—H7A	108.6	C15—C16—H16	119.8
N2—C7—H7B	108.6	C17—C16—H16	119.8
C6—C7—H7B	108.6	C16—C17—C12	120.47 (16)
H7A—C7—H7B	107.5	C16—C17—H17	119.8
N2—C8—C10	121.76 (14)	C12—C17—H17	119.8
N2—C8—C9	118.48 (13)	C1—N1—H1A	120.0
C10—C8—C9	119.75 (15)	C1—N1—H1B	120.0
C8—C9—H9A	109.5	H1A—N1—H1B	120.0
C8—C9—H9B	109.5	C8—N2—C7	125.86 (14)
H9A—C9—H9B	109.5	C8—N2—H2A	117.1
C8—C9—H9C	109.5	C7—N2—H2A	117.1
H9A—C9—H9C	109.5
N1—C1—C2—C3	179.97 (16)	C8—C10—C11—C12	172.88 (14)
C6—C1—C2—C3	−0.5 (2)	O1—C11—C12—C13	9.5 (2)
C1—C2—C3—C4	0.4 (3)	C10—C11—C12—C13	−170.01 (14)
C2—C3—C4—C5	−0.2 (3)	O1—C11—C12—C17	−169.53 (15)
C3—C4—C5—C6	0.0 (3)	C10—C11—C12—C17	11.0 (2)
C4—C5—C6—C1	0.0 (2)	C17—C12—C13—C14	−0.9 (2)
C4—C5—C6—C7	−177.47 (16)	C11—C12—C13—C14	−179.89 (15)
N1—C1—C6—C5	179.81 (15)	C12—C13—C14—C15	0.9 (3)
C2—C1—C6—C5	0.3 (2)	C13—C14—C15—C16	0.1 (3)
N1—C1—C6—C7	−2.6 (2)	C14—C15—C16—C17	−1.1 (3)
C2—C1—C6—C7	177.83 (14)	C15—C16—C17—C12	1.1 (3)
C5—C6—C7—N2	−19.4 (2)	C13—C12—C17—C16	−0.1 (2)
C1—C6—C7—N2	163.10 (14)	C11—C12—C17—C16	178.86 (15)
N2—C8—C10—C11	0.8 (3)	C10—C8—N2—C7	−174.01 (15)
C9—C8—C10—C11	−178.05 (17)	C9—C8—N2—C7	4.9 (3)
C8—C10—C11—O1	−6.6 (3)	C6—C7—N2—C8	−90.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.99	2.6619 (17)	134
N1—H1A···O1i	0.86	2.27	3.0009 (19)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.99	2.6619 (17)	134
N1—H1A⋯O1i	0.86	2.27	3.0009 (19)	143

Symmetry code: (i) .