4-Bromo-2-(dieth-oxy-meth-yl)phenyl benzoate.

In the title compound, C18H19BrO4, the aromatic rings enclose a dihedral angle of 81.9 (7)°. There are no short directional contacts in the crystal structure.

Related literature

For the biological activity of ester derivatives, see: Bi et al. (2012 ▶); Bartzatt et al. (2004 ▶); Anadu et al. (2006 ▶).

Experimental

Crystal data

C18H19BrO4

M = 379.24

Triclinic,

a = 8.2662 (8) Å

b = 9.6378 (10) Å

c = 11.6224 (13) Å

α = 99.927 (5)°

β = 93.700 (5)°

γ = 101.178 (5)°

V = 890.16 (16) Å3

Z = 2

Mo Kα radiation

μ = 2.33 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T min = 0.497, T max = 0.594

16152 measured reflections

4493 independent reflections

3037 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.01

4493 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006351/bt6892sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006351/bt6892Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006351/bt6892Isup3.cml

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

C18H19BrO4	Z = 2
Mr = 379.24	F(000) = 388
Triclinic, P1	Dx = 1.415 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2662 (8) Å	Cell parameters from 8834 reflections
b = 9.6378 (10) Å	θ = 2.1–31.2°
c = 11.6224 (13) Å	µ = 2.33 mm−1
α = 99.927 (5)°	T = 293 K
β = 93.700 (5)°	Block, colourless
γ = 101.178 (5)°	0.35 × 0.30 × 0.25 mm
V = 890.16 (16) Å3

Bruker Kappa APEXII CCD diffractometer	4493 independent reflections
Radiation source: fine-focus sealed tube	3037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scan	θmax = 28.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→11
Tmin = 0.497, Tmax = 0.594	k = −12→12
16152 measured reflections	l = −14→15

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0325P)2 + 0.2669P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4493 reflections	Δρmax = 0.46 e Å−3
209 parameters	Δρmin = −0.42 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: 0.0293 (17)

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
C1	1.0177 (3)	0.1162 (2)	0.14518 (19)	0.0568 (5)
H1	1.0276	0.2024	0.1179	0.068*
C2	1.1551 (3)	0.0569 (3)	0.1588 (2)	0.0668 (6)
H2	1.2575	0.1035	0.1415	0.080*
C3	1.1409 (3)	−0.0706 (3)	0.1979 (2)	0.0686 (6)
H3	1.2335	−0.1108	0.2067	0.082*
C4	0.9906 (3)	−0.1388 (2)	0.2238 (2)	0.0657 (6)
H4	0.9814	−0.2257	0.2500	0.079*
C5	0.8522 (3)	−0.0800 (2)	0.21151 (19)	0.0560 (5)
H5	0.7504	−0.1266	0.2299	0.067*
C6	0.8660 (2)	0.0487 (2)	0.17159 (16)	0.0446 (4)
C7	0.7144 (3)	0.1076 (2)	0.16072 (17)	0.0476 (5)
C8	0.6138 (2)	0.3097 (2)	0.12700 (17)	0.0454 (4)
C9	0.4947 (3)	0.2747 (2)	0.03277 (18)	0.0530 (5)
H9	0.5006	0.2030	−0.0306	0.064*
C10	0.3663 (3)	0.3469 (2)	0.03332 (19)	0.0553 (5)
H10	0.2848	0.3249	−0.0298	0.066*
C11	0.3603 (2)	0.4517 (2)	0.12799 (18)	0.0495 (5)
C12	0.4820 (2)	0.4902 (2)	0.22060 (17)	0.0477 (5)
H12	0.4769	0.5639	0.2827	0.057*
C13	0.6130 (2)	0.4189 (2)	0.22129 (17)	0.0440 (4)
C14	0.7505 (2)	0.4552 (2)	0.32109 (18)	0.0487 (5)
H14	0.8563	0.4704	0.2868	0.058*
C15	0.8756 (3)	0.6431 (3)	0.4779 (2)	0.0728 (7)
H15A	0.9786	0.6372	0.4438	0.087*
H15B	0.8675	0.5876	0.5402	0.087*
C16	0.8736 (4)	0.7952 (3)	0.5262 (2)	0.0831 (8)
H16A	0.9657	0.8344	0.5850	0.125*
H16B	0.7720	0.8003	0.5607	0.125*
H16C	0.8819	0.8497	0.4642	0.125*
C17	0.5999 (3)	0.3033 (3)	0.4376 (2)	0.0698 (6)
H17A	0.5091	0.2600	0.3771	0.084*
H17B	0.5723	0.3875	0.4843	0.084*
C18	0.6251 (4)	0.1991 (4)	0.5128 (3)	0.1005 (10)
H18A	0.5260	0.1717	0.5494	0.151*
H18B	0.7155	0.2424	0.5721	0.151*
H18C	0.6501	0.1153	0.4657	0.151*
O1	0.57904 (18)	0.05021 (16)	0.17780 (15)	0.0657 (4)
O2	0.74639 (16)	0.23833 (14)	0.12732 (12)	0.0502 (3)
O3	0.74890 (16)	0.34407 (15)	0.38518 (12)	0.0535 (3)
O4	0.73826 (17)	0.58602 (15)	0.38984 (13)	0.0578 (4)
Br1	0.17952 (3)	0.54626 (3)	0.13035 (2)	0.07463 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0560 (12)	0.0532 (12)	0.0665 (14)	0.0203 (10)	0.0098 (10)	0.0140 (10)
C2	0.0549 (13)	0.0715 (16)	0.0812 (16)	0.0235 (12)	0.0154 (12)	0.0195 (13)
C3	0.0660 (15)	0.0711 (16)	0.0759 (16)	0.0377 (13)	0.0041 (12)	0.0085 (13)
C4	0.0794 (17)	0.0487 (12)	0.0752 (15)	0.0271 (12)	0.0037 (12)	0.0142 (11)
C5	0.0601 (13)	0.0463 (12)	0.0606 (13)	0.0147 (10)	0.0032 (10)	0.0044 (10)
C6	0.0501 (11)	0.0403 (10)	0.0418 (10)	0.0145 (8)	0.0012 (8)	−0.0010 (8)
C7	0.0491 (11)	0.0401 (10)	0.0499 (11)	0.0116 (9)	0.0018 (9)	−0.0028 (9)
C8	0.0437 (10)	0.0399 (10)	0.0541 (12)	0.0137 (8)	0.0050 (8)	0.0073 (9)
C9	0.0616 (13)	0.0442 (11)	0.0495 (12)	0.0127 (10)	−0.0018 (10)	−0.0005 (9)
C10	0.0558 (12)	0.0502 (12)	0.0557 (12)	0.0102 (10)	−0.0116 (10)	0.0062 (10)
C11	0.0440 (10)	0.0445 (11)	0.0608 (13)	0.0146 (8)	−0.0032 (9)	0.0096 (9)
C12	0.0469 (10)	0.0429 (10)	0.0517 (11)	0.0150 (8)	−0.0022 (9)	0.0007 (9)
C13	0.0402 (9)	0.0417 (10)	0.0495 (11)	0.0105 (8)	−0.0001 (8)	0.0058 (8)
C14	0.0423 (10)	0.0471 (11)	0.0551 (12)	0.0118 (8)	−0.0024 (9)	0.0052 (9)
C15	0.0678 (15)	0.0647 (15)	0.0731 (16)	0.0076 (12)	−0.0277 (12)	−0.0026 (12)
C16	0.0846 (18)	0.0742 (17)	0.0724 (17)	0.0070 (14)	−0.0140 (14)	−0.0166 (13)
C17	0.0651 (15)	0.0801 (17)	0.0676 (15)	0.0161 (13)	0.0103 (12)	0.0209 (13)
C18	0.104 (2)	0.092 (2)	0.116 (2)	0.0156 (18)	0.0205 (19)	0.0523 (19)
O1	0.0468 (8)	0.0520 (9)	0.0981 (12)	0.0104 (7)	0.0066 (8)	0.0144 (8)
O2	0.0469 (7)	0.0433 (7)	0.0639 (9)	0.0181 (6)	0.0090 (6)	0.0086 (6)
O3	0.0459 (7)	0.0551 (8)	0.0607 (8)	0.0136 (6)	−0.0023 (6)	0.0135 (7)
O4	0.0532 (8)	0.0498 (8)	0.0622 (9)	0.0137 (6)	−0.0156 (7)	−0.0073 (7)
Br1	0.05575 (16)	0.07410 (19)	0.0983 (2)	0.03299 (12)	−0.00794 (12)	0.01173 (14)

C1—C6	1.375 (3)	C11—Br1	1.8944 (19)
C1—C2	1.380 (3)	C12—C13	1.391 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.368 (3)	C13—C14	1.515 (3)
C2—H2	0.9300	C14—O4	1.397 (2)
C3—C4	1.366 (3)	C14—O3	1.405 (2)
C3—H3	0.9300	C14—H14	0.9800
C4—C5	1.382 (3)	C15—O4	1.432 (2)
C4—H4	0.9300	C15—C16	1.480 (3)
C5—C6	1.385 (3)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—C7	1.480 (3)	C16—H16A	0.9600
C7—O1	1.193 (2)	C16—H16B	0.9600
C7—O2	1.364 (2)	C16—H16C	0.9600
C8—C9	1.374 (3)	C17—O3	1.427 (3)
C8—C13	1.384 (3)	C17—C18	1.475 (4)
C8—O2	1.402 (2)	C17—H17A	0.9700
C9—C10	1.377 (3)	C17—H17B	0.9700
C9—H9	0.9300	C18—H18A	0.9600
C10—C11	1.370 (3)	C18—H18B	0.9600
C10—H10	0.9300	C18—H18C	0.9600
C11—C12	1.374 (3)
C6—C1—C2	120.4 (2)	C8—C13—C12	117.63 (17)
C6—C1—H1	119.8	C8—C13—C14	119.86 (16)
C2—C1—H1	119.8	C12—C13—C14	122.51 (17)
C3—C2—C1	120.1 (2)	O4—C14—O3	113.44 (17)
C3—C2—H2	120.0	O4—C14—C13	107.35 (15)
C1—C2—H2	120.0	O3—C14—C13	112.85 (15)
C4—C3—C2	120.0 (2)	O4—C14—H14	107.6
C4—C3—H3	120.0	O3—C14—H14	107.6
C2—C3—H3	120.0	C13—C14—H14	107.6
C3—C4—C5	120.6 (2)	O4—C15—C16	109.0 (2)
C3—C4—H4	119.7	O4—C15—H15A	109.9
C5—C4—H4	119.7	C16—C15—H15A	109.9
C4—C5—C6	119.5 (2)	O4—C15—H15B	109.9
C4—C5—H5	120.2	C16—C15—H15B	109.9
C6—C5—H5	120.2	H15A—C15—H15B	108.3
C1—C6—C5	119.40 (18)	C15—C16—H16A	109.5
C1—C6—C7	123.17 (18)	C15—C16—H16B	109.5
C5—C6—C7	117.43 (19)	H16A—C16—H16B	109.5
O1—C7—O2	122.72 (18)	C15—C16—H16C	109.5
O1—C7—C6	125.59 (19)	H16A—C16—H16C	109.5
O2—C7—C6	111.68 (17)	H16B—C16—H16C	109.5
C9—C8—C13	122.30 (17)	O3—C17—C18	108.7 (2)
C9—C8—O2	120.00 (17)	O3—C17—H17A	110.0
C13—C8—O2	117.64 (16)	C18—C17—H17A	110.0
C8—C9—C10	119.24 (18)	O3—C17—H17B	110.0
C8—C9—H9	120.4	C18—C17—H17B	110.0
C10—C9—H9	120.4	H17A—C17—H17B	108.3
C11—C10—C9	119.18 (18)	C17—C18—H18A	109.5
C11—C10—H10	120.4	C17—C18—H18B	109.5
C9—C10—H10	120.4	H18A—C18—H18B	109.5
C10—C11—C12	121.75 (18)	C17—C18—H18C	109.5
C10—C11—Br1	118.92 (14)	H18A—C18—H18C	109.5
C12—C11—Br1	119.33 (15)	H18B—C18—H18C	109.5
C11—C12—C13	119.83 (18)	C7—O2—C8	115.71 (15)
C11—C12—H12	120.1	C14—O3—C17	115.33 (16)
C13—C12—H12	120.1	C14—O4—C15	112.95 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.93	2.42	2.740 (3)	100
C12—H12···O4	0.93	2.38	2.699 (2)	100
C17—H17B···O4	0.97	2.58	2.905 (3)	100