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

In the title compound, C19H13BrO3, 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 77.20 (5)°. In the crystal, C-H⋯O contacts connect the mol-ecules into undulating sheets parallel (100).

Related literature

For general information about phenacyl bromide derivatives, 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

C19H13BrO3

M = 369.20

Monoclinic,

a = 5.2888 (2) Å

b = 14.9139 (6) Å

c = 20.0275 (8) Å

β = 100.867 (2)°

V = 1551.37 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.66 mm−1

T = 200 K

0.35 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.656, T max = 0.746

14937 measured reflections

3848 independent reflections

2712 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.080

S = 1.02

3848 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.56 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 ▶); 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/S160053681300843X/qk2054sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300843X/qk2054Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300843X/qk2054Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300843X/qk2054Isup4.cml

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

C19H13BrO3	F(000) = 744
Mr = 369.20	Dx = 1.581 Mg m−3
Monoclinic, P21/c	Melting point = 406–404 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.2888 (2) Å	Cell parameters from 4237 reflections
b = 14.9139 (6) Å	θ = 2.5–24.2°
c = 20.0275 (8) Å	µ = 2.66 mm−1
β = 100.867 (2)°	T = 200 K
V = 1551.37 (11) Å3	Platelet, colourless
Z = 4	0.35 × 0.16 × 0.07 mm

Bruker APEXII CCD diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	2712 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −6→7
Tmin = 0.656, Tmax = 0.746	k = −19→19
14937 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0326P)2 + 0.6176P] where P = (Fo2 + 2Fc2)/3
3848 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

	x	y	z	Uiso*/Ueq
Br1	1.05155 (5)	−0.337459 (17)	−0.082915 (14)	0.05483 (11)
O1	0.7161 (3)	0.01926 (12)	0.09358 (8)	0.0504 (4)
O2	1.0379 (3)	0.07451 (10)	0.20022 (7)	0.0383 (3)
O3	0.8211 (3)	−0.03018 (11)	0.24600 (9)	0.0561 (5)
C1	0.9200 (4)	−0.02042 (15)	0.10258 (10)	0.0324 (5)
C2	1.1300 (4)	0.00494 (16)	0.16236 (11)	0.0392 (5)
H2A	1.1784	−0.0480	0.1918	0.047*
H2B	1.2847	0.0257	0.1457	0.047*
C3	0.8587 (4)	0.04763 (15)	0.23606 (11)	0.0356 (5)
C11	0.9659 (4)	−0.09457 (14)	0.05693 (10)	0.0301 (4)
C12	0.7748 (4)	−0.11433 (15)	0.00128 (11)	0.0364 (5)
H12	0.6242	−0.0782	−0.0078	0.044*
C13	0.7996 (4)	−0.18520 (15)	−0.04088 (12)	0.0396 (5)
H13	0.6679	−0.1981	−0.0789	0.047*
C14	1.0190 (4)	−0.23729 (14)	−0.02702 (11)	0.0359 (5)
C15	1.2131 (4)	−0.21891 (16)	0.02701 (12)	0.0411 (5)
H15	1.3637	−0.2550	0.0356	0.049*
C16	1.1865 (4)	−0.14699 (15)	0.06894 (11)	0.0376 (5)
H16	1.3206	−0.1335	0.1063	0.045*
C20	0.7119 (4)	0.12388 (14)	0.25724 (10)	0.0317 (4)
C21	0.6958 (4)	0.20194 (15)	0.22036 (11)	0.0401 (5)
H21	0.7954	0.2086	0.1858	0.048*
C22	0.5341 (5)	0.27215 (16)	0.23293 (13)	0.0505 (6)
H22	0.5277	0.3263	0.2077	0.061*
C23	0.3868 (5)	0.26250 (17)	0.28116 (13)	0.0486 (6)
H23	0.2727	0.3093	0.2880	0.058*
C24	0.3998 (4)	0.18466 (16)	0.32119 (12)	0.0397 (5)
C25	0.2488 (4)	0.17481 (19)	0.37226 (14)	0.0517 (7)
H25	0.1312	0.2208	0.3785	0.062*
C26	0.2694 (5)	0.1008 (2)	0.41240 (14)	0.0572 (7)
H26	0.1656	0.0950	0.4460	0.069*
C27	0.4432 (5)	0.03358 (19)	0.40408 (13)	0.0525 (7)
H27	0.4620	−0.0169	0.4335	0.063*
C28	0.5868 (4)	0.03887 (16)	0.35440 (11)	0.0406 (5)
H28	0.7011	−0.0086	0.3491	0.049*
C29	0.5685 (4)	0.11383 (14)	0.31069 (10)	0.0316 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.0741 (2)	0.04066 (15)	0.05347 (17)	0.00681 (13)	0.02159 (13)	−0.00796 (12)
O1	0.0365 (9)	0.0641 (12)	0.0454 (10)	0.0178 (8)	−0.0056 (7)	−0.0172 (8)
O2	0.0327 (8)	0.0439 (9)	0.0381 (8)	−0.0067 (7)	0.0063 (6)	−0.0090 (7)
O3	0.0770 (12)	0.0334 (10)	0.0665 (12)	0.0033 (9)	0.0357 (10)	−0.0005 (8)
C1	0.0258 (10)	0.0375 (12)	0.0325 (11)	0.0027 (9)	0.0020 (8)	−0.0001 (9)
C2	0.0280 (11)	0.0523 (14)	0.0365 (12)	0.0004 (10)	0.0040 (9)	−0.0084 (10)
C3	0.0354 (11)	0.0387 (13)	0.0314 (11)	−0.0017 (9)	0.0029 (9)	−0.0038 (9)
C11	0.0241 (10)	0.0378 (12)	0.0280 (10)	0.0017 (8)	0.0045 (8)	0.0034 (9)
C12	0.0293 (11)	0.0410 (13)	0.0367 (12)	0.0059 (9)	0.0007 (9)	−0.0017 (9)
C13	0.0378 (12)	0.0413 (13)	0.0365 (12)	0.0011 (10)	−0.0009 (9)	−0.0036 (10)
C14	0.0439 (12)	0.0322 (12)	0.0349 (12)	0.0037 (10)	0.0156 (10)	0.0017 (9)
C15	0.0343 (11)	0.0449 (14)	0.0443 (13)	0.0134 (10)	0.0083 (10)	0.0025 (10)
C16	0.0258 (10)	0.0519 (15)	0.0333 (11)	0.0064 (9)	0.0009 (9)	0.0000 (10)
C20	0.0306 (10)	0.0303 (11)	0.0311 (11)	−0.0012 (9)	−0.0020 (8)	−0.0042 (9)
C21	0.0464 (13)	0.0365 (12)	0.0344 (12)	−0.0041 (10)	0.0002 (10)	0.0003 (10)
C22	0.0635 (16)	0.0312 (13)	0.0491 (15)	0.0058 (12)	−0.0093 (13)	0.0008 (11)
C23	0.0470 (14)	0.0399 (14)	0.0519 (15)	0.0100 (11)	−0.0082 (12)	−0.0152 (11)
C24	0.0323 (11)	0.0432 (13)	0.0390 (12)	−0.0018 (10)	−0.0046 (9)	−0.0175 (10)
C25	0.0337 (12)	0.0657 (19)	0.0556 (16)	−0.0054 (12)	0.0080 (11)	−0.0334 (14)
C26	0.0491 (15)	0.076 (2)	0.0510 (16)	−0.0235 (14)	0.0201 (12)	−0.0227 (14)
C27	0.0607 (16)	0.0560 (17)	0.0428 (14)	−0.0237 (13)	0.0147 (12)	−0.0050 (12)
C28	0.0440 (12)	0.0374 (13)	0.0404 (13)	−0.0073 (10)	0.0078 (10)	−0.0025 (10)
C29	0.0279 (10)	0.0334 (12)	0.0302 (11)	−0.0044 (9)	−0.0025 (8)	−0.0079 (8)

Br1—C14	1.894 (2)	C16—H16	0.9500
O1—C1	1.213 (2)	C20—C21	1.373 (3)
O2—C3	1.353 (3)	C20—C29	1.432 (3)
O2—C2	1.424 (2)	C21—C22	1.404 (3)
O3—C3	1.200 (3)	C21—H21	0.9500
C1—C11	1.484 (3)	C22—C23	1.358 (4)
C1—C2	1.520 (3)	C22—H22	0.9500
C2—H2A	0.9900	C23—C24	1.405 (3)
C2—H2B	0.9900	C23—H23	0.9500
C3—C20	1.483 (3)	C24—C25	1.419 (3)
C11—C16	1.387 (3)	C24—C29	1.424 (3)
C11—C12	1.388 (3)	C25—C26	1.357 (4)
C12—C13	1.374 (3)	C25—H25	0.9500
C12—H12	0.9500	C26—C27	1.392 (4)
C13—C14	1.380 (3)	C26—H26	0.9500
C13—H13	0.9500	C27—C28	1.363 (3)
C14—C15	1.371 (3)	C27—H27	0.9500
C15—C16	1.386 (3)	C28—C29	1.412 (3)
C15—H15	0.9500	C28—H28	0.9500
C3—O2—C2	114.25 (17)	C21—C20—C29	120.2 (2)
O1—C1—C11	121.08 (18)	C21—C20—C3	118.6 (2)
O1—C1—C2	119.53 (19)	C29—C20—C3	120.87 (19)
C11—C1—C2	119.38 (17)	C20—C21—C22	120.9 (2)
O2—C2—C1	109.17 (16)	C20—C21—H21	119.5
O2—C2—H2A	109.8	C22—C21—H21	119.5
C1—C2—H2A	109.8	C23—C22—C21	119.9 (2)
O2—C2—H2B	109.8	C23—C22—H22	120.0
C1—C2—H2B	109.8	C21—C22—H22	120.0
H2A—C2—H2B	108.3	C22—C23—C24	121.4 (2)
O3—C3—O2	121.9 (2)	C22—C23—H23	119.3
O3—C3—C20	125.6 (2)	C24—C23—H23	119.3
O2—C3—C20	112.42 (19)	C23—C24—C25	121.6 (2)
C16—C11—C12	118.8 (2)	C23—C24—C29	119.6 (2)
C16—C11—C1	122.91 (18)	C25—C24—C29	118.9 (2)
C12—C11—C1	118.29 (17)	C26—C25—C24	121.2 (2)
C13—C12—C11	121.14 (19)	C26—C25—H25	119.4
C13—C12—H12	119.4	C24—C25—H25	119.4
C11—C12—H12	119.4	C25—C26—C27	119.7 (2)
C12—C13—C14	118.9 (2)	C25—C26—H26	120.1
C12—C13—H13	120.6	C27—C26—H26	120.1
C14—C13—H13	120.6	C28—C27—C26	121.1 (3)
C15—C14—C13	121.5 (2)	C28—C27—H27	119.4
C15—C14—Br1	119.07 (16)	C26—C27—H27	119.4
C13—C14—Br1	119.46 (17)	C27—C28—C29	121.0 (2)
C14—C15—C16	119.11 (19)	C27—C28—H28	119.5
C14—C15—H15	120.4	C29—C28—H28	119.5
C16—C15—H15	120.4	C28—C29—C24	117.9 (2)
C15—C16—C11	120.6 (2)	C28—C29—C20	124.22 (19)
C15—C16—H16	119.7	C24—C29—C20	117.9 (2)
C11—C16—H16	119.7
C3—O2—C2—C1	71.6 (2)	O2—C3—C20—C29	−162.04 (17)
O1—C1—C2—O2	1.4 (3)	C29—C20—C21—C22	−1.7 (3)
C11—C1—C2—O2	−177.41 (18)	C3—C20—C21—C22	172.2 (2)
C2—O2—C3—O3	14.5 (3)	C20—C21—C22—C23	−1.4 (3)
C2—O2—C3—C20	−162.58 (16)	C21—C22—C23—C24	2.6 (4)
O1—C1—C11—C16	−173.9 (2)	C22—C23—C24—C25	179.1 (2)
C2—C1—C11—C16	4.9 (3)	C22—C23—C24—C29	−0.7 (3)
O1—C1—C11—C12	3.5 (3)	C23—C24—C25—C26	−177.5 (2)
C2—C1—C11—C12	−177.7 (2)	C29—C24—C25—C26	2.3 (3)
C16—C11—C12—C13	1.0 (3)	C24—C25—C26—C27	0.7 (4)
C1—C11—C12—C13	−176.5 (2)	C25—C26—C27—C28	−2.6 (4)
C11—C12—C13—C14	0.2 (3)	C26—C27—C28—C29	1.5 (4)
C12—C13—C14—C15	−1.1 (3)	C27—C28—C29—C24	1.5 (3)
C12—C13—C14—Br1	178.04 (17)	C27—C28—C29—C20	−179.7 (2)
C13—C14—C15—C16	0.7 (3)	C23—C24—C29—C28	176.54 (19)
Br1—C14—C15—C16	−178.38 (17)	C25—C24—C29—C28	−3.3 (3)
C14—C15—C16—C11	0.5 (3)	C23—C24—C29—C20	−2.4 (3)
C12—C11—C16—C15	−1.4 (3)	C25—C24—C29—C20	177.78 (19)
C1—C11—C16—C15	176.0 (2)	C21—C20—C29—C28	−175.28 (19)
O3—C3—C20—C21	−152.8 (2)	C3—C20—C29—C28	11.0 (3)
O2—C3—C20—C21	24.1 (3)	C21—C20—C29—C24	3.6 (3)
O3—C3—C20—C29	21.0 (3)	C3—C20—C29—C24	−170.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.95	2.41	3.240 (3)	146
C23—H23···O3ii	0.95	2.51	3.292 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.95	2.41	3.240 (3)	146
C23—H23⋯O3ii	0.95	2.51	3.292 (3)	140

Symmetry codes: (i) ; (ii) .