(E)-1-(4-Amino-phen-yl)-3-(naphthalen-2-yl)prop-2-en-1-one.

The mol-ecule of the title chalcone derivative, C(19)H(15)NO, exists in a trans configuration with respect to the C=C double bond. The mol-ecule is slightly twisted with a dihedral angle of 6.12 (12)° between the benzene ring and the naphthalene ring system. The prop-2-en-1-one bridge is nearly planar, with an r.m.s. deviation of 0.0194 (2), and makes dihedral angles of 8.05 (19) and 11.47 (18)° with the benzene ring and the naphthalene ring system, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along the b axis. Weak N-H⋯π and C-H⋯π inter-actions and a short N⋯O contact [2.974 (4) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008 ▶); Horkaew et al. (2010 ▶). For background to and applications of chalcones, see: Bandgar & Gawande (2010 ▶); Cheng et al. (2008) ▶; Gaber et al. (2008 ▶); Nerya et al. (2004 ▶); Nowakowska et al. (2008 ▶); Patil et al. (2007 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶); Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C19H15NO

M = 273.32

Orthorhombic,

a = 5.7422 (6) Å

b = 9.8022 (10) Å

c = 25.504 (3) Å

V = 1435.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.32 × 0.28 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.976, T max = 0.994

8109 measured reflections

1940 independent reflections

1633 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.119

S = 1.14

1940 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811014024/rz2579sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014024/rz2579Isup2.hkl

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

C19H15NO	Dx = 1.265 Mg m−3
Mr = 273.32	Melting point = 416–417 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1940 reflections
a = 5.7422 (6) Å	θ = 2.2–27.5°
b = 9.8022 (10) Å	µ = 0.08 mm−1
c = 25.504 (3) Å	T = 100 K
V = 1435.5 (3) Å3	Plate, yellow
Z = 4	0.32 × 0.28 × 0.07 mm
F(000) = 576

Bruker APEX DUO CCD area-detector diffractometer	1940 independent reflections
Radiation source: sealed tube	1633 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→7
Tmin = 0.976, Tmax = 0.994	k = −9→12
8109 measured reflections	l = −32→33

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0233P)2 + 1.3561P] where P = (Fo2 + 2Fc2)/3
1940 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 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 100.0 (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	1.1598 (4)	0.7032 (2)	0.85128 (9)	0.0266 (5)
N1	0.5373 (7)	1.1585 (3)	0.74175 (13)	0.0339 (8)
H2N1	0.409 (8)	1.195 (4)	0.7515 (15)	0.045 (13)*
H1N1	0.599 (7)	1.187 (4)	0.7112 (14)	0.033 (11)*
C1	0.8419 (6)	0.8481 (3)	0.83133 (11)	0.0201 (7)
C2	0.9516 (6)	0.9000 (3)	0.78648 (12)	0.0224 (7)
H2A	1.0945	0.8641	0.7763	0.027*
C3	0.8535 (6)	1.0026 (3)	0.75714 (12)	0.0230 (7)
H3A	0.9314	1.0356	0.7278	0.028*
C4	0.6354 (6)	1.0583 (3)	0.77112 (12)	0.0233 (7)
C5	0.5252 (6)	1.0072 (3)	0.81610 (12)	0.0232 (7)
H5A	0.3827	1.0434	0.8264	0.028*
C6	0.6244 (6)	0.9045 (3)	0.84519 (12)	0.0219 (7)
H6A	0.5466	0.8715	0.8746	0.026*
C7	0.9597 (6)	0.7405 (3)	0.86224 (13)	0.0222 (7)
C8	0.8373 (6)	0.6782 (3)	0.90735 (12)	0.0221 (7)
H8A	0.6818	0.7000	0.9133	0.027*
C9	0.9441 (6)	0.5920 (3)	0.93962 (11)	0.0198 (7)
H9A	1.0988	0.5718	0.9321	0.024*
C10	0.8433 (6)	0.5257 (3)	0.98562 (12)	0.0187 (7)
C11	0.9577 (6)	0.4164 (3)	1.00866 (11)	0.0204 (7)
H11A	1.1021	0.3900	0.9956	0.025*
C12	0.8612 (6)	0.3438 (3)	1.05134 (12)	0.0199 (7)
C13	0.9733 (6)	0.2294 (3)	1.07446 (12)	0.0234 (7)
H13A	1.1171	0.2010	1.0617	0.028*
C14	0.8731 (7)	0.1609 (3)	1.11511 (13)	0.0275 (8)
H14A	0.9490	0.0864	1.1299	0.033*
C15	0.6544 (7)	0.2022 (3)	1.13492 (13)	0.0276 (8)
H15A	0.5864	0.1540	1.1624	0.033*
C16	0.5423 (7)	0.3123 (3)	1.11405 (12)	0.0263 (7)
H16A	0.3998	0.3395	1.1279	0.032*
C17	0.6402 (6)	0.3855 (3)	1.07164 (11)	0.0196 (7)
C18	0.5282 (6)	0.4987 (3)	1.04803 (12)	0.0220 (7)
H18A	0.3853	0.5277	1.0611	0.026*
C19	0.6240 (6)	0.5658 (3)	1.00685 (12)	0.0211 (7)
H19A	0.5453	0.6395	0.9922	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (13)	0.0254 (11)	0.0297 (12)	0.0044 (12)	0.0068 (11)	0.0020 (10)
N1	0.0305 (19)	0.0385 (18)	0.0326 (17)	0.0104 (17)	0.0064 (16)	0.0122 (15)
C1	0.0240 (18)	0.0180 (15)	0.0185 (14)	−0.0039 (15)	−0.0014 (14)	−0.0037 (12)
C2	0.0215 (17)	0.0213 (15)	0.0244 (16)	−0.0025 (15)	0.0041 (14)	−0.0062 (13)
C3	0.0257 (18)	0.0216 (15)	0.0216 (15)	−0.0037 (17)	0.0047 (15)	−0.0005 (13)
C4	0.0236 (17)	0.0226 (15)	0.0237 (15)	−0.0024 (16)	−0.0032 (15)	−0.0039 (13)
C5	0.0183 (17)	0.0272 (16)	0.0242 (15)	0.0003 (15)	0.0017 (14)	−0.0039 (14)
C6	0.0196 (17)	0.0233 (15)	0.0229 (15)	−0.0050 (15)	0.0028 (14)	−0.0033 (13)
C7	0.0227 (17)	0.0184 (15)	0.0256 (16)	−0.0021 (15)	0.0001 (15)	−0.0051 (13)
C8	0.0242 (18)	0.0152 (14)	0.0269 (15)	−0.0016 (15)	0.0052 (15)	−0.0045 (13)
C9	0.0203 (16)	0.0113 (13)	0.0278 (16)	−0.0040 (13)	0.0037 (14)	−0.0071 (12)
C10	0.0207 (16)	0.0121 (14)	0.0234 (15)	−0.0012 (13)	−0.0001 (14)	−0.0065 (11)
C11	0.0153 (15)	0.0220 (15)	0.0240 (15)	−0.0012 (15)	0.0005 (14)	−0.0075 (13)
C12	0.0202 (17)	0.0171 (14)	0.0225 (14)	−0.0037 (15)	−0.0026 (14)	−0.0074 (12)
C13	0.0234 (17)	0.0188 (15)	0.0281 (16)	−0.0019 (15)	−0.0033 (15)	−0.0065 (13)
C14	0.035 (2)	0.0181 (15)	0.0297 (17)	0.0039 (16)	−0.0075 (17)	−0.0003 (14)
C15	0.035 (2)	0.0226 (16)	0.0255 (16)	−0.0092 (17)	0.0008 (17)	0.0016 (13)
C16	0.0245 (18)	0.0296 (17)	0.0249 (16)	−0.0078 (17)	0.0015 (15)	−0.0075 (14)
C17	0.0198 (16)	0.0196 (14)	0.0196 (14)	−0.0024 (14)	0.0009 (14)	−0.0085 (12)
C18	0.0188 (16)	0.0220 (15)	0.0251 (15)	0.0022 (15)	0.0027 (14)	−0.0069 (13)
C19	0.0221 (17)	0.0152 (14)	0.0261 (15)	0.0084 (15)	−0.0014 (14)	−0.0020 (13)

O1—C7	1.238 (4)	C9—H9A	0.9300
N1—C4	1.358 (4)	C10—C11	1.388 (4)
N1—H2N1	0.86 (4)	C10—C19	1.426 (5)
N1—H1N1	0.90 (4)	C11—C12	1.413 (4)
C1—C2	1.402 (4)	C11—H11A	0.9300
C1—C6	1.411 (5)	C12—C13	1.421 (4)
C1—C7	1.480 (4)	C12—C17	1.430 (5)
C2—C3	1.374 (4)	C13—C14	1.363 (5)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.412 (5)	C14—C15	1.413 (5)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.403 (4)	C15—C16	1.364 (5)
C5—C6	1.374 (4)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.415 (4)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C8	1.480 (4)	C17—C18	1.417 (4)
C8—C9	1.330 (4)	C18—C19	1.356 (4)
C8—H8A	0.9300	C18—H18A	0.9300
C9—C10	1.461 (4)	C19—H19A	0.9300
C4—N1—H2N1	120 (3)	C11—C10—C19	118.1 (3)
C4—N1—H1N1	123 (2)	C11—C10—C9	119.7 (3)
H2N1—N1—H1N1	117 (4)	C19—C10—C9	122.1 (3)
C2—C1—C6	117.4 (3)	C10—C11—C12	121.9 (3)
C2—C1—C7	119.2 (3)	C10—C11—H11A	119.0
C6—C1—C7	123.4 (3)	C12—C11—H11A	119.0
C3—C2—C1	121.7 (3)	C11—C12—C13	122.6 (3)
C3—C2—H2A	119.1	C11—C12—C17	118.9 (3)
C1—C2—H2A	119.1	C13—C12—C17	118.5 (3)
C2—C3—C4	120.6 (3)	C14—C13—C12	120.9 (3)
C2—C3—H3A	119.7	C14—C13—H13A	119.6
C4—C3—H3A	119.7	C12—C13—H13A	119.6
N1—C4—C5	121.5 (3)	C13—C14—C15	120.4 (3)
N1—C4—C3	120.6 (3)	C13—C14—H14A	119.8
C5—C4—C3	117.9 (3)	C15—C14—H14A	119.8
C6—C5—C4	121.1 (3)	C16—C15—C14	120.4 (3)
C6—C5—H5A	119.4	C16—C15—H15A	119.8
C4—C5—H5A	119.4	C14—C15—H15A	119.8
C5—C6—C1	121.2 (3)	C15—C16—C17	120.8 (3)
C5—C6—H6A	119.4	C15—C16—H16A	119.6
C1—C6—H6A	119.4	C17—C16—H16A	119.6
O1—C7—C8	119.6 (3)	C16—C17—C18	122.8 (3)
O1—C7—C1	121.0 (3)	C16—C17—C12	118.9 (3)
C8—C7—C1	119.4 (3)	C18—C17—C12	118.2 (3)
C9—C8—C7	121.6 (3)	C19—C18—C17	121.7 (3)
C9—C8—H8A	119.2	C19—C18—H18A	119.2
C7—C8—H8A	119.2	C17—C18—H18A	119.2
C8—C9—C10	126.7 (3)	C18—C19—C10	121.2 (3)
C8—C9—H9A	116.7	C18—C19—H19A	119.4
C10—C9—H9A	116.7	C10—C19—H19A	119.4
C6—C1—C2—C3	0.5 (4)	C9—C10—C11—C12	−176.3 (3)
C7—C1—C2—C3	−178.1 (3)	C10—C11—C12—C13	178.3 (3)
C1—C2—C3—C4	−0.7 (5)	C10—C11—C12—C17	−0.7 (4)
C2—C3—C4—N1	−179.2 (3)	C11—C12—C13—C14	−179.0 (3)
C2—C3—C4—C5	1.0 (5)	C17—C12—C13—C14	0.0 (4)
N1—C4—C5—C6	179.1 (3)	C12—C13—C14—C15	0.2 (5)
C3—C4—C5—C6	−1.0 (5)	C13—C14—C15—C16	−0.8 (5)
C4—C5—C6—C1	0.9 (5)	C14—C15—C16—C17	1.2 (5)
C2—C1—C6—C5	−0.6 (4)	C15—C16—C17—C18	178.7 (3)
C7—C1—C6—C5	178.0 (3)	C15—C16—C17—C12	−1.0 (5)
C2—C1—C7—O1	5.3 (4)	C11—C12—C17—C16	179.4 (3)
C6—C1—C7—O1	−173.3 (3)	C13—C12—C17—C16	0.4 (4)
C2—C1—C7—C8	−175.6 (3)	C11—C12—C17—C18	−0.3 (4)
C6—C1—C7—C8	5.8 (4)	C13—C12—C17—C18	−179.3 (3)
O1—C7—C8—C9	6.4 (5)	C16—C17—C18—C19	−178.9 (3)
C1—C7—C8—C9	−172.7 (3)	C12—C17—C18—C19	0.8 (4)
C7—C8—C9—C10	179.1 (3)	C17—C18—C19—C10	−0.3 (5)
C8—C9—C10—C11	165.8 (3)	C11—C10—C19—C18	−0.6 (4)
C8—C9—C10—C19	−11.5 (5)	C9—C10—C19—C18	176.8 (3)
C19—C10—C11—C12	1.1 (4)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1···Cg1ii	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A···Cg3iii	0.93	2.82	3.513 (3)	132
C11—H11A···Cg3iv	0.93	2.92	3.631 (3)	135
C13—H13A···Cg2iv	0.93	2.86	3.551 (3)	132
C16—H16A···Cg1iii	0.93	2.87	3.603 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1⋯Cg1ii	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A⋯Cg3iii	0.93	2.82	3.513 (3)	132
C11—H11A⋯Cg3iv	0.93	2.92	3.631 (3)	135
C13—H13A⋯Cg2iv	0.93	2.86	3.551 (3)	132
C16—H16A⋯Cg1iii	0.93	2.87	3.603 (4)	136

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