2-(4-Chloro-phen-yl)-2-oxoethyl naphthalene-1-carboxyl-ate.

In the title compound, C19H13ClO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.16 (3)°. In the crystal, C-H⋯O contacts connect the mol-ecules into undulating sheets parallel to the bc plane.

Related literature

For general information about phenyl benzoates, see: Rather & Reid (1919 ▶). For the photolytic properties of phenyl benzoates, see: Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶). For synthetic applications of phenyl benzoates, see: Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H13ClO3

M = 324.74

Monoclinic,

a = 5.2708 (1) Å

b = 14.8465 (4) Å

c = 19.8427 (5) Å

β = 100.383 (1)°

V = 1527.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 200 K

0.37 × 0.35 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.941, T max = 1.000

14592 measured reflections

3769 independent reflections

2984 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.103

S = 1.02

3769 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006958/kq2003sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006958/kq2003Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006958/kq2003Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006958/kq2003Isup4.cml

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

C19H13ClO3	F(000) = 672
Mr = 324.74	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Melting point = 396–394 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.2708 (1) Å	Cell parameters from 6659 reflections
b = 14.8465 (4) Å	θ = 2.5–28.3°
c = 19.8427 (5) Å	µ = 0.26 mm−1
β = 100.383 (1)°	T = 200 K
V = 1527.32 (6) Å3	Block, colourless
Z = 4	0.37 × 0.35 × 0.27 mm

Bruker APEXII CCD diffractometer	3769 independent reflections
Radiation source: fine-focus sealed tube	2984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→4
Tmin = 0.941, Tmax = 1.000	k = −19→19
14592 measured reflections	l = −26→26

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3
3769 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	1.04341 (9)	0.83154 (3)	−0.08650 (2)	0.05829 (14)
O1	0.71978 (19)	0.48481 (8)	0.09291 (5)	0.0498 (3)
O2	1.04495 (18)	0.43162 (7)	0.20029 (5)	0.0401 (2)
O3	0.8225 (2)	0.53669 (7)	0.24573 (6)	0.0570 (3)
C1	0.9224 (2)	0.52533 (9)	0.10107 (6)	0.0340 (3)
C2	1.1344 (2)	0.50163 (11)	0.16112 (7)	0.0408 (3)
H2A	1.2901	0.4813	0.1440	0.049*
H2B	1.1806	0.5554	0.1903	0.049*
C3	0.8633 (3)	0.45846 (9)	0.23619 (7)	0.0370 (3)
C11	0.9666 (2)	0.59907 (9)	0.05398 (6)	0.0313 (3)
C12	1.1866 (2)	0.65299 (10)	0.06517 (7)	0.0391 (3)
H12	1.3210	0.6407	0.1028	0.047*
C13	1.2108 (3)	0.72426 (10)	0.02184 (8)	0.0430 (3)
H13	1.3601	0.7614	0.0298	0.052*
C14	1.0158 (3)	0.74075 (9)	−0.03304 (7)	0.0384 (3)
C15	0.7980 (3)	0.68741 (10)	−0.04616 (7)	0.0421 (3)
H15	0.6668	0.6989	−0.0847	0.050*
C16	0.7743 (2)	0.61712 (9)	−0.00232 (7)	0.0381 (3)
H16	0.6243	0.5804	−0.0107	0.046*
C20	0.7172 (2)	0.38165 (8)	0.25836 (6)	0.0336 (3)
C21	0.7052 (3)	0.30251 (10)	0.22178 (7)	0.0424 (3)
H21	0.8074	0.2956	0.1873	0.051*
C22	0.5434 (3)	0.23170 (10)	0.23488 (8)	0.0523 (4)
H22	0.5388	0.1771	0.2098	0.063*
C23	0.3936 (3)	0.24148 (10)	0.28341 (8)	0.0505 (4)
H23	0.2801	0.1942	0.2906	0.061*
C24	0.4034 (3)	0.32039 (10)	0.32326 (7)	0.0412 (3)
C25	0.2497 (3)	0.33038 (13)	0.37451 (9)	0.0546 (4)
H25	0.1335	0.2836	0.3811	0.066*
C26	0.2647 (3)	0.40503 (14)	0.41426 (9)	0.0597 (5)
H26	0.1594	0.4106	0.4482	0.072*
C27	0.4364 (3)	0.47393 (12)	0.40503 (8)	0.0543 (4)
H27	0.4505	0.5254	0.4339	0.065*
C28	0.5840 (3)	0.46848 (10)	0.35528 (7)	0.0425 (3)
H28	0.6973	0.5166	0.3496	0.051*
C29	0.5706 (2)	0.39209 (9)	0.31191 (7)	0.0340 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0760 (3)	0.0426 (2)	0.0591 (3)	−0.00666 (18)	0.0197 (2)	0.01078 (17)
O1	0.0353 (5)	0.0632 (7)	0.0466 (6)	−0.0177 (5)	−0.0047 (4)	0.0150 (5)
O2	0.0345 (5)	0.0452 (5)	0.0400 (5)	0.0055 (4)	0.0053 (4)	0.0087 (4)
O3	0.0793 (8)	0.0324 (5)	0.0669 (7)	−0.0031 (5)	0.0335 (6)	0.0017 (5)
C1	0.0268 (6)	0.0416 (7)	0.0324 (6)	−0.0030 (5)	0.0025 (5)	−0.0002 (5)
C2	0.0301 (6)	0.0530 (8)	0.0378 (7)	−0.0022 (6)	0.0024 (5)	0.0075 (6)
C3	0.0379 (7)	0.0374 (7)	0.0340 (6)	0.0006 (5)	0.0024 (5)	0.0033 (5)
C11	0.0265 (6)	0.0362 (6)	0.0313 (6)	−0.0016 (5)	0.0051 (4)	−0.0032 (5)
C12	0.0288 (6)	0.0494 (8)	0.0376 (7)	−0.0067 (5)	0.0018 (5)	−0.0014 (6)
C13	0.0369 (7)	0.0465 (8)	0.0464 (8)	−0.0134 (6)	0.0094 (6)	−0.0025 (6)
C14	0.0457 (7)	0.0334 (6)	0.0387 (7)	−0.0021 (6)	0.0145 (6)	−0.0007 (5)
C15	0.0402 (7)	0.0453 (8)	0.0377 (7)	−0.0023 (6)	−0.0010 (5)	0.0040 (6)
C16	0.0311 (6)	0.0412 (7)	0.0395 (7)	−0.0071 (5)	0.0000 (5)	0.0010 (5)
C20	0.0337 (6)	0.0314 (6)	0.0329 (6)	0.0026 (5)	−0.0020 (5)	0.0048 (5)
C21	0.0510 (8)	0.0368 (7)	0.0358 (7)	0.0036 (6)	−0.0021 (6)	0.0001 (5)
C22	0.0688 (10)	0.0337 (7)	0.0469 (8)	−0.0047 (7)	−0.0100 (7)	−0.0002 (6)
C23	0.0525 (9)	0.0401 (8)	0.0520 (9)	−0.0110 (7)	−0.0095 (7)	0.0150 (7)
C24	0.0335 (7)	0.0443 (7)	0.0416 (7)	0.0013 (6)	−0.0046 (5)	0.0173 (6)
C25	0.0371 (8)	0.0688 (11)	0.0573 (10)	0.0028 (7)	0.0065 (7)	0.0309 (8)
C26	0.0513 (9)	0.0785 (12)	0.0530 (9)	0.0224 (9)	0.0195 (8)	0.0224 (9)
C27	0.0618 (10)	0.0570 (10)	0.0457 (8)	0.0220 (8)	0.0138 (7)	0.0056 (7)
C28	0.0462 (8)	0.0396 (7)	0.0415 (7)	0.0073 (6)	0.0074 (6)	0.0031 (6)
C29	0.0305 (6)	0.0336 (6)	0.0349 (6)	0.0048 (5)	−0.0022 (5)	0.0078 (5)

Cl1—C14	1.7375 (14)	C16—H16	0.9500
O1—C1	1.2110 (15)	C20—C21	1.3765 (19)
O2—C3	1.3523 (17)	C20—C29	1.4305 (19)
O2—C2	1.4279 (16)	C21—C22	1.407 (2)
O3—C3	1.2023 (17)	C21—H21	0.9500
C1—C11	1.4847 (18)	C22—C23	1.358 (2)
C1—C2	1.5206 (18)	C22—H22	0.9500
C2—H2A	0.9900	C23—C24	1.409 (2)
C2—H2B	0.9900	C23—H23	0.9500
C3—C20	1.4862 (18)	C24—C25	1.418 (2)
C11—C16	1.3926 (18)	C24—C29	1.4255 (19)
C11—C12	1.3933 (17)	C25—C26	1.354 (3)
C12—C13	1.384 (2)	C25—H25	0.9500
C12—H12	0.9500	C26—C27	1.400 (3)
C13—C14	1.378 (2)	C26—H26	0.9500
C13—H13	0.9500	C27—C28	1.365 (2)
C14—C15	1.380 (2)	C27—H27	0.9500
C15—C16	1.379 (2)	C28—C29	1.4178 (19)
C15—H15	0.9500	C28—H28	0.9500
C3—O2—C2	114.00 (11)	C21—C20—C29	120.29 (12)
O1—C1—C11	121.12 (11)	C21—C20—C3	118.42 (13)
O1—C1—C2	119.71 (12)	C29—C20—C3	120.99 (12)
C11—C1—C2	119.16 (11)	C20—C21—C22	120.81 (15)
O2—C2—C1	109.09 (10)	C20—C21—H21	119.6
O2—C2—H2A	109.9	C22—C21—H21	119.6
C1—C2—H2A	109.9	C23—C22—C21	120.00 (14)
O2—C2—H2B	109.9	C23—C22—H22	120.0
C1—C2—H2B	109.9	C21—C22—H22	120.0
H2A—C2—H2B	108.3	C22—C23—C24	121.30 (14)
O3—C3—O2	122.10 (13)	C22—C23—H23	119.3
O3—C3—C20	125.28 (13)	C24—C23—H23	119.3
O2—C3—C20	112.55 (11)	C23—C24—C25	121.45 (15)
C16—C11—C12	118.80 (12)	C23—C24—C29	119.55 (14)
C16—C11—C1	118.20 (11)	C25—C24—C29	119.00 (15)
C12—C11—C1	122.94 (11)	C26—C25—C24	121.49 (15)
C13—C12—C11	120.50 (12)	C26—C25—H25	119.3
C13—C12—H12	119.7	C24—C25—H25	119.3
C11—C12—H12	119.7	C25—C26—C27	119.55 (15)
C14—C13—C12	119.20 (12)	C25—C26—H26	120.2
C14—C13—H13	120.4	C27—C26—H26	120.2
C12—C13—H13	120.4	C28—C27—C26	121.18 (17)
C13—C14—C15	121.57 (13)	C28—C27—H27	119.4
C13—C14—Cl1	119.20 (11)	C26—C27—H27	119.4
C15—C14—Cl1	119.23 (11)	C27—C28—C29	120.92 (15)
C16—C15—C14	118.84 (13)	C27—C28—H28	119.5
C16—C15—H15	120.6	C29—C28—H28	119.5
C14—C15—H15	120.6	C28—C29—C24	117.78 (13)
C15—C16—C11	121.07 (12)	C28—C29—C20	124.27 (12)
C15—C16—H16	119.5	C24—C29—C20	117.94 (12)
C11—C16—H16	119.5
C3—O2—C2—C1	−71.19 (14)	O2—C3—C20—C29	162.30 (11)
O1—C1—C2—O2	−1.16 (19)	C29—C20—C21—C22	1.9 (2)
C11—C1—C2—O2	177.87 (11)	C3—C20—C21—C22	−171.84 (13)
C2—O2—C3—O3	−14.99 (19)	C20—C21—C22—C23	1.0 (2)
C2—O2—C3—C20	162.17 (10)	C21—C22—C23—C24	−2.4 (2)
O1—C1—C11—C16	−3.7 (2)	C22—C23—C24—C25	−179.23 (14)
C2—C1—C11—C16	177.32 (12)	C22—C23—C24—C29	0.9 (2)
O1—C1—C11—C12	173.71 (14)	C23—C24—C25—C26	177.95 (14)
C2—C1—C11—C12	−5.3 (2)	C29—C24—C25—C26	−2.2 (2)
C16—C11—C12—C13	1.3 (2)	C24—C25—C26—C27	−0.3 (2)
C1—C11—C12—C13	−176.09 (13)	C25—C26—C27—C28	1.9 (2)
C11—C12—C13—C14	−0.7 (2)	C26—C27—C28—C29	−0.9 (2)
C12—C13—C14—C15	−0.6 (2)	C27—C28—C29—C24	−1.65 (19)
C12—C13—C14—Cl1	178.78 (11)	C27—C28—C29—C20	179.49 (13)
C13—C14—C15—C16	1.2 (2)	C23—C24—C29—C28	−177.01 (12)
Cl1—C14—C15—C16	−178.12 (11)	C25—C24—C29—C28	3.14 (18)
C14—C15—C16—C11	−0.6 (2)	C23—C24—C29—C20	1.92 (18)
C12—C11—C16—C15	−0.6 (2)	C25—C24—C29—C20	−177.93 (11)
C1—C11—C16—C15	176.89 (13)	C21—C20—C29—C28	175.54 (12)
O3—C3—C20—C21	153.08 (15)	C3—C20—C29—C28	−10.86 (19)
O2—C3—C20—C21	−23.97 (16)	C21—C20—C29—C24	−3.32 (17)
O3—C3—C20—C29	−20.6 (2)	C3—C20—C29—C24	170.29 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.95	2.41	3.2583 (16)	148
C23—H23···O3ii	0.95	2.48	3.2618 (19)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.95	2.41	3.2583 (16)	148
C23—H23⋯O3ii	0.95	2.48	3.2618 (19)	140

Symmetry codes: (i) ; (ii) .