Crystal structure of N-[(2-hy-droxy-naphthalen-1-yl)(4-methyl-phen-yl)meth-yl]acetamide.

In the title mol-ecule, C20H19NO2, the naphthalene ring system subtends a dihedral angle of 82.50 (7)° with the benzene ring and an intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, which generate C(8) chains propagating in the [010] direction. The crystal structure also features weak π-π inter-actions [centroid-centroid separation = 3.7246 (10) Å].

Related literature

For background to N-(substituted phen­yl)acetamides, see: Schleiss et al. (2008 ▸). For further synthetic details, see: Shaterian et al. (2008 ▸). For related structures, see: Mosslemin et al. (2007 ▸); NizamMohideen et al. (2009 ▸).

Experimental

Crystal data

C20H19NO2

M = 305.36

Monoclinic,

a = 10.4324 (4) Å

b = 14.0786 (5) Å

c = 11.0356 (4) Å

β = 98.741 (2)°

V = 1602.01 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.980, T max = 0.984

12272 measured reflections

2821 independent reflections

2391 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.05

2821 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015004661/hb7375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004661/hb7375Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015004661/hb7375Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015004661/hb7375fig1.tif

The mol­ecular configuration of (I). Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015004661/hb7375fig2.tif

The packing arrangement of mol­ecules viewed down the b axis.

CCDC reference: 959797

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

C20H19NO2	F(000) = 648
Mr = 305.36	Dx = 1.266 Mg m−3Dm = 1.264 Mg m−3Dm measured by not measured
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6588 reflections
a = 10.4324 (4) Å	θ = 2.5–28.2°
b = 14.0786 (5) Å	µ = 0.08 mm−1
c = 11.0356 (4) Å	T = 296 K
β = 98.741 (2)°	Block, colourless
V = 1602.01 (10) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	2391 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.980, Tmax = 0.984	k = −15→16
12272 measured reflections	l = −13→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.5039P] where P = (Fo2 + 2Fc2)/3
2821 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.70578 (14)	0.25289 (10)	0.87937 (14)	0.0381 (3)
H1	0.6938	0.3100	0.9271	0.046*
C2	0.78237 (14)	0.18214 (10)	0.96674 (14)	0.0379 (3)
C3	0.72170 (16)	0.11312 (12)	1.02635 (16)	0.0510 (4)
H3	0.6318	0.1079	1.0110	0.061*
C4	0.79230 (18)	0.05162 (13)	1.10855 (18)	0.0598 (5)
H4	0.7488	0.0058	1.1474	0.072*
C5	0.92559 (18)	0.05652 (12)	1.13422 (16)	0.0527 (4)
C6	1.0028 (2)	−0.01018 (15)	1.2240 (2)	0.0748 (6)
H6A	1.0934	0.0045	1.2300	0.112*
H6B	0.9881	−0.0744	1.1961	0.112*
H6C	0.9761	−0.0032	1.3030	0.112*
C7	0.98531 (17)	0.12598 (14)	1.07495 (17)	0.0578 (5)
H7	1.0752	0.1312	1.0904	0.069*
C8	0.91576 (16)	0.18805 (12)	0.99343 (16)	0.0508 (4)
H8	0.9593	0.2346	0.9559	0.061*
C9	0.83298 (15)	0.36630 (11)	0.77479 (15)	0.0426 (4)
C10	0.89465 (19)	0.38493 (14)	0.66304 (18)	0.0614 (5)
H10A	0.8856	0.3298	0.6112	0.092*
H10B	0.9850	0.3988	0.6872	0.092*
H10C	0.8529	0.4381	0.6191	0.092*
C11	0.57167 (14)	0.21783 (10)	0.82499 (13)	0.0358 (3)
C12	0.56126 (15)	0.14446 (10)	0.74112 (14)	0.0393 (4)
C13	0.44045 (16)	0.10999 (11)	0.68525 (15)	0.0466 (4)
H13	0.4361	0.0611	0.6280	0.056*
C14	0.32992 (16)	0.14825 (12)	0.71506 (16)	0.0493 (4)
H14	0.2501	0.1255	0.6772	0.059*
C15	0.33371 (15)	0.22181 (12)	0.80244 (15)	0.0448 (4)
C16	0.45625 (14)	0.25743 (10)	0.85831 (13)	0.0385 (4)
C17	0.45539 (16)	0.33110 (12)	0.94630 (16)	0.0492 (4)
H17	0.5338	0.3556	0.9851	0.059*
C18	0.34242 (18)	0.36669 (15)	0.97517 (19)	0.0632 (5)
H18	0.3450	0.4150	1.0330	0.076*
C19	0.22255 (18)	0.33162 (16)	0.9191 (2)	0.0685 (6)
H19	0.1459	0.3565	0.9391	0.082*
C20	0.21922 (17)	0.26107 (14)	0.83527 (19)	0.0601 (5)
H20	0.1393	0.2378	0.7983	0.072*
N1	0.77811 (12)	0.28136 (9)	0.78136 (12)	0.0424 (3)
H1A	0.7856	0.2408	0.7246	0.051*
O1	0.67338 (11)	0.10791 (8)	0.71078 (11)	0.0497 (3)
H1B	0.6595	0.0546	0.6818	0.075*
O2	0.83171 (12)	0.42693 (8)	0.85572 (11)	0.0548 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0395 (8)	0.0307 (7)	0.0462 (8)	−0.0022 (6)	0.0133 (7)	−0.0001 (6)
C2	0.0374 (8)	0.0347 (8)	0.0420 (8)	−0.0016 (6)	0.0073 (6)	−0.0045 (6)
C3	0.0395 (9)	0.0529 (10)	0.0601 (10)	−0.0034 (7)	0.0065 (8)	0.0127 (8)
C4	0.0596 (11)	0.0546 (11)	0.0628 (12)	−0.0048 (8)	0.0017 (9)	0.0175 (9)
C5	0.0580 (11)	0.0473 (10)	0.0486 (10)	0.0063 (8)	−0.0051 (8)	−0.0065 (7)
C6	0.0827 (15)	0.0659 (13)	0.0670 (13)	0.0196 (11)	−0.0172 (11)	−0.0003 (10)
C7	0.0391 (9)	0.0678 (12)	0.0630 (11)	0.0021 (8)	−0.0038 (8)	−0.0070 (9)
C8	0.0410 (9)	0.0523 (10)	0.0587 (10)	−0.0089 (7)	0.0063 (7)	−0.0005 (8)
C9	0.0406 (8)	0.0347 (8)	0.0531 (9)	−0.0017 (6)	0.0090 (7)	0.0078 (7)
C10	0.0683 (12)	0.0529 (10)	0.0681 (12)	−0.0112 (9)	0.0271 (10)	0.0078 (9)
C11	0.0382 (8)	0.0299 (7)	0.0399 (8)	−0.0006 (6)	0.0079 (6)	0.0058 (6)
C12	0.0444 (8)	0.0305 (7)	0.0443 (8)	0.0006 (6)	0.0108 (7)	0.0051 (6)
C13	0.0550 (10)	0.0365 (8)	0.0472 (9)	−0.0065 (7)	0.0045 (7)	−0.0016 (7)
C14	0.0449 (9)	0.0481 (9)	0.0527 (10)	−0.0073 (7)	0.0004 (7)	0.0039 (7)
C15	0.0400 (9)	0.0455 (9)	0.0493 (9)	−0.0001 (7)	0.0078 (7)	0.0082 (7)
C16	0.0405 (8)	0.0361 (8)	0.0400 (8)	−0.0001 (6)	0.0090 (6)	0.0063 (6)
C17	0.0449 (9)	0.0520 (10)	0.0528 (10)	−0.0019 (7)	0.0138 (7)	−0.0055 (8)
C18	0.0571 (11)	0.0668 (12)	0.0699 (12)	0.0024 (9)	0.0240 (9)	−0.0157 (10)
C19	0.0452 (10)	0.0796 (14)	0.0850 (14)	0.0078 (9)	0.0238 (10)	−0.0075 (11)
C20	0.0389 (9)	0.0704 (12)	0.0715 (12)	−0.0007 (8)	0.0103 (8)	−0.0005 (10)
N1	0.0474 (8)	0.0336 (7)	0.0491 (8)	−0.0052 (5)	0.0166 (6)	−0.0001 (5)
O1	0.0517 (7)	0.0348 (6)	0.0656 (8)	0.0005 (5)	0.0183 (6)	−0.0076 (5)
O2	0.0699 (8)	0.0352 (6)	0.0617 (8)	−0.0099 (5)	0.0179 (6)	0.0019 (5)

C1—N1	1.4657 (19)	C10—H10B	0.9600
C1—C11	1.519 (2)	C10—H10C	0.9600
C1—C2	1.525 (2)	C11—C12	1.380 (2)
C1—H1	0.9800	C11—C16	1.425 (2)
C2—C3	1.380 (2)	C12—O1	1.3653 (18)
C2—C8	1.380 (2)	C12—C13	1.403 (2)
C3—C4	1.383 (2)	C13—C14	1.358 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.378 (3)	C14—C15	1.412 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C7	1.377 (3)	C15—C20	1.412 (2)
C5—C6	1.506 (3)	C15—C16	1.423 (2)
C6—H6A	0.9600	C16—C17	1.422 (2)
C6—H6B	0.9600	C17—C18	1.362 (2)
C6—H6C	0.9600	C17—H17	0.9300
C7—C8	1.379 (3)	C18—C19	1.398 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—H8	0.9300	C19—C20	1.354 (3)
C9—O2	1.237 (2)	C19—H19	0.9300
C9—N1	1.3325 (19)	C20—H20	0.9300
C9—C10	1.498 (2)	N1—H1A	0.8600
C10—H10A	0.9600	O1—H1B	0.8200
N1—C1—C11	110.12 (12)	H10A—C10—H10C	109.5
N1—C1—C2	111.48 (12)	H10B—C10—H10C	109.5
C11—C1—C2	113.60 (11)	C12—C11—C16	118.85 (14)
N1—C1—H1	107.1	C12—C11—C1	118.83 (13)
C11—C1—H1	107.1	C16—C11—C1	122.32 (13)
C2—C1—H1	107.1	O1—C12—C11	117.61 (13)
C3—C2—C8	117.48 (15)	O1—C12—C13	120.52 (14)
C3—C2—C1	121.80 (13)	C11—C12—C13	121.84 (14)
C8—C2—C1	120.65 (14)	C14—C13—C12	119.71 (15)
C2—C3—C4	121.09 (16)	C14—C13—H13	120.1
C2—C3—H3	119.5	C12—C13—H13	120.1
C4—C3—H3	119.5	C13—C14—C15	121.33 (15)
C5—C4—C3	121.59 (17)	C13—C14—H14	119.3
C5—C4—H4	119.2	C15—C14—H14	119.3
C3—C4—H4	119.2	C14—C15—C20	121.69 (16)
C7—C5—C4	116.94 (16)	C14—C15—C16	118.98 (15)
C7—C5—C6	121.31 (18)	C20—C15—C16	119.33 (16)
C4—C5—C6	121.74 (19)	C17—C16—C15	117.02 (14)
C5—C6—H6A	109.5	C17—C16—C11	123.71 (14)
C5—C6—H6B	109.5	C15—C16—C11	119.26 (14)
H6A—C6—H6B	109.5	C18—C17—C16	121.57 (16)
C5—C6—H6C	109.5	C18—C17—H17	119.2
H6A—C6—H6C	109.5	C16—C17—H17	119.2
H6B—C6—H6C	109.5	C17—C18—C19	120.91 (18)
C5—C7—C8	121.93 (16)	C17—C18—H18	119.5
C5—C7—H7	119.0	C19—C18—H18	119.5
C8—C7—H7	119.0	C20—C19—C18	119.33 (17)
C7—C8—C2	120.96 (16)	C20—C19—H19	120.3
C7—C8—H8	119.5	C18—C19—H19	120.3
C2—C8—H8	119.5	C19—C20—C15	121.82 (18)
O2—C9—N1	121.89 (15)	C19—C20—H20	119.1
O2—C9—C10	121.78 (14)	C15—C20—H20	119.1
N1—C9—C10	116.33 (15)	C9—N1—C1	124.00 (13)
C9—C10—H10A	109.5	C9—N1—H1A	118.0
C9—C10—H10B	109.5	C1—N1—H1A	118.0
H10A—C10—H10B	109.5	C12—O1—H1B	109.5
C9—C10—H10C	109.5
N1—C1—C2—C3	−148.79 (15)	C11—C12—C13—C14	−1.0 (2)
C11—C1—C2—C3	−23.7 (2)	C12—C13—C14—C15	−0.6 (2)
N1—C1—C2—C8	34.33 (19)	C13—C14—C15—C20	−179.08 (16)
C11—C1—C2—C8	159.45 (14)	C13—C14—C15—C16	1.2 (2)
C8—C2—C3—C4	−0.8 (3)	C14—C15—C16—C17	−179.63 (15)
C1—C2—C3—C4	−177.72 (16)	C20—C15—C16—C17	0.6 (2)
C2—C3—C4—C5	−0.1 (3)	C14—C15—C16—C11	−0.2 (2)
C3—C4—C5—C7	0.5 (3)	C20—C15—C16—C11	−179.93 (15)
C3—C4—C5—C6	179.83 (18)	C12—C11—C16—C17	178.05 (14)
C4—C5—C7—C8	−0.1 (3)	C1—C11—C16—C17	−1.4 (2)
C6—C5—C7—C8	−179.40 (18)	C12—C11—C16—C15	−1.3 (2)
C5—C7—C8—C2	−0.8 (3)	C1—C11—C16—C15	179.22 (13)
C3—C2—C8—C7	1.2 (2)	C15—C16—C17—C18	−0.6 (2)
C1—C2—C8—C7	178.18 (15)	C11—C16—C17—C18	−179.98 (16)
N1—C1—C11—C12	56.06 (17)	C16—C17—C18—C19	0.1 (3)
C2—C1—C11—C12	−69.78 (17)	C17—C18—C19—C20	0.2 (3)
N1—C1—C11—C16	−124.50 (14)	C18—C19—C20—C15	−0.2 (3)
C2—C1—C11—C16	109.65 (15)	C14—C15—C20—C19	179.99 (18)
C16—C11—C12—O1	179.95 (12)	C16—C15—C20—C19	−0.3 (3)
C1—C11—C12—O1	−0.6 (2)	O2—C9—N1—C1	3.4 (2)
C16—C11—C12—C13	2.0 (2)	C10—C9—N1—C1	−175.71 (14)
C1—C11—C12—C13	−178.56 (13)	C11—C1—N1—C9	125.81 (15)
O1—C12—C13—C14	−178.92 (14)	C2—C1—N1—C9	−107.16 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.20	2.7396 (16)	121
O1—H1B···O2i	0.82	1.85	2.6498 (15)	165

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO1	0.86	2.20	2.7396(16)	121
O1H1BO2i	0.82	1.85	2.6498(15)	165

Symmetry code: (i) .