(E)-3-(1,3-Benzodioxol-4-yl)-2-(4-bromo­phen­yl)acrylic acid

In the solid-state structure of the title compound, C₁₆H₁₁BrO₄, the configuration about the double bond is E, and the mean planes through the two aromatic rings are inclined to one another by 63.71 (12)°. In the crystal structure, symmetry-related mol­ecules are linked by O—H...O hydrogen bonds, forming centrosymmetric carboxylic acid dimers. The crystal structure is further stabilized by C—H...Br and C—H...O inter­molecular hydrogen bonds, leading to the formation of a layer-like structure, which extends in the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.039
• wR factor = 0.086
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(E)-3-(1,3-Benzodioxol-4-yl)-2-(4-bromophenyl)acrylic acid

Crystal data

C16H11BrO4	F(000) = 696
Mr = 347.16	Dx = 1.644 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12162 reflections
a = 5.6331 (6) Å	θ = 2.6–29.6°
b = 8.2283 (5) Å	µ = 2.94 mm^−1
c = 30.259 (3) Å	T = 173 K
β = 91.239 (8)°	Rod, pale yellow
V = 1402.2 (2) Å^3	0.45 × 0.15 × 0.15 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	3793 independent reflections
Radiation source: fine-focus sealed tube	2830 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 6.67 pixels mm^-1	θmax = 29.2°, θmin = 2.6°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2003)	k = −9→11
Tmin = 0.469, Tmax = 0.644	l = −41→41
17926 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.7151P] where P = (Fo^2 + 2Fc^2)/3
3793 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.55190 (5)	−0.38608 (4)	0.23898 (1)	0.0438 (1)
O1	1.2738 (4)	0.5041 (3)	0.09414 (8)	0.0604 (8)
O2	0.9722 (4)	0.4073 (3)	0.04842 (7)	0.0487 (7)
O3	0.1065 (3)	−0.0750 (2)	0.04575 (5)	0.0339 (5)
O4	0.2673 (3)	0.1274 (2)	0.00736 (5)	0.0365 (5)
C1	0.7630 (4)	0.2519 (3)	0.10504 (8)	0.0330 (7)
C2	0.7675 (5)	0.2199 (3)	0.15133 (8)	0.0369 (8)
C3	0.9451 (5)	0.2821 (4)	0.17847 (9)	0.0431 (9)
C4	1.1280 (5)	0.3785 (4)	0.16232 (10)	0.0471 (9)
C5	1.1193 (5)	0.4134 (3)	0.11840 (10)	0.0429 (9)
C6	0.9395 (5)	0.3537 (3)	0.09090 (9)	0.0364 (8)
C7	1.1700 (6)	0.5185 (4)	0.05098 (12)	0.0556 (11)
C8	0.5858 (4)	0.1906 (3)	0.07332 (8)	0.0314 (7)
C9	0.4432 (4)	0.0595 (3)	0.07677 (7)	0.0282 (7)
C10	0.4544 (4)	−0.0596 (3)	0.11388 (7)	0.0279 (7)
C11	0.2761 (4)	−0.0688 (3)	0.14472 (8)	0.0324 (7)
C12	0.3013 (4)	−0.1677 (3)	0.18163 (7)	0.0337 (7)
C13	0.5067 (4)	−0.2583 (3)	0.18690 (7)	0.0321 (7)
C14	0.6808 (4)	−0.2583 (3)	0.15554 (8)	0.0354 (8)
C15	0.6542 (4)	−0.1577 (3)	0.11912 (8)	0.0330 (7)
C16	0.2589 (4)	0.0308 (3)	0.04211 (7)	0.0283 (7)
H2	0.64640	0.15480	0.16370	0.0440*
H3	0.94300	0.25860	0.20920	0.0520*
H4	1.25250	0.41770	0.18110	0.0560*
H4O	0.15670	0.10610	−0.00970	0.0440*
H7A	1.28790	0.49080	0.02840	0.0670*
H7B	1.11480	0.63120	0.04570	0.0670*
H8	0.56850	0.25100	0.04670	0.0380*
H11	0.13520	−0.00670	0.14050	0.0390*
H12	0.17990	−0.17300	0.20290	0.0400*
H13	0.81650	−0.32610	0.15890	0.0420*
H15	0.77370	−0.15560	0.09750	0.0400*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0553 (2)	0.0449 (2)	0.0305 (1)	−0.0015 (1)	−0.0126 (1)	0.0050 (1)
O1	0.0526 (13)	0.0515 (14)	0.0766 (15)	−0.0234 (11)	−0.0095 (11)	0.0011 (12)
O2	0.0523 (12)	0.0464 (13)	0.0471 (11)	−0.0157 (10)	−0.0029 (9)	0.0045 (9)
O3	0.0322 (9)	0.0366 (11)	0.0324 (8)	−0.0067 (7)	−0.0109 (7)	0.0050 (7)
O4	0.0367 (9)	0.0387 (10)	0.0336 (8)	−0.0072 (8)	−0.0128 (7)	0.0072 (7)
C1	0.0288 (12)	0.0321 (13)	0.0379 (12)	0.0040 (10)	−0.0049 (9)	−0.0058 (10)
C2	0.0327 (13)	0.0431 (16)	0.0346 (12)	0.0026 (11)	−0.0068 (10)	−0.0079 (11)
C3	0.0416 (15)	0.0459 (17)	0.0412 (13)	0.0048 (13)	−0.0112 (11)	−0.0107 (12)
C4	0.0392 (14)	0.0435 (16)	0.0577 (16)	0.0005 (13)	−0.0189 (12)	−0.0148 (14)
C5	0.0350 (14)	0.0332 (16)	0.0602 (17)	0.0007 (11)	−0.0078 (12)	−0.0063 (12)
C6	0.0357 (13)	0.0305 (15)	0.0428 (13)	0.0019 (10)	−0.0043 (10)	−0.0059 (10)
C7	0.0538 (19)	0.0395 (18)	0.073 (2)	−0.0128 (15)	−0.0087 (16)	0.0080 (15)
C8	0.0285 (12)	0.0360 (14)	0.0295 (10)	0.0013 (10)	−0.0034 (9)	−0.0006 (9)
C9	0.0232 (11)	0.0344 (13)	0.0268 (10)	0.0026 (9)	−0.0027 (8)	−0.0042 (9)
C10	0.0244 (11)	0.0328 (13)	0.0262 (10)	−0.0005 (9)	−0.0050 (8)	−0.0028 (8)
C11	0.0247 (11)	0.0413 (15)	0.0310 (11)	0.0041 (10)	−0.0047 (9)	−0.0026 (10)
C12	0.0304 (12)	0.0440 (15)	0.0265 (10)	−0.0003 (11)	−0.0034 (9)	−0.0012 (10)
C13	0.0360 (13)	0.0328 (13)	0.0269 (10)	−0.0035 (10)	−0.0096 (9)	0.0013 (9)
C14	0.0301 (13)	0.0407 (15)	0.0350 (12)	0.0071 (11)	−0.0070 (10)	0.0010 (10)
C15	0.0263 (11)	0.0405 (15)	0.0323 (11)	0.0031 (10)	0.0000 (9)	−0.0001 (10)
C16	0.0260 (11)	0.0316 (13)	0.0272 (10)	0.0021 (9)	−0.0036 (8)	−0.0012 (9)

Geometric parameters (Å, º)

Br1—C13	1.907 (2)	C9—C16	1.479 (3)
O1—C5	1.372 (4)	C10—C15	1.391 (3)
O1—C7	1.424 (4)	C10—C11	1.388 (3)
O2—C6	1.375 (3)	C11—C12	1.387 (3)
O2—C7	1.443 (4)	C12—C13	1.383 (3)
O3—C16	1.229 (3)	C13—C14	1.379 (3)
O4—C16	1.320 (3)	C14—C15	1.384 (3)
O4—H4O	0.8200	C2—H2	0.9500
C1—C2	1.425 (3)	C3—H3	0.9500
C1—C8	1.460 (3)	C4—H4	0.9500
C1—C6	1.375 (4)	C7—H7A	0.9900
C2—C3	1.379 (4)	C7—H7B	0.9900
C3—C4	1.397 (4)	C8—H8	0.9500
C4—C5	1.360 (4)	C11—H11	0.9500
C5—C6	1.387 (4)	C12—H12	0.9500
C8—C9	1.350 (3)	C14—H13	0.9500
C9—C10	1.491 (3)	C15—H15	0.9500
Br1···C12^i	3.426 (2)	C16···C6^vii	3.548 (4)
Br1···H4^ii	2.9000	C16···O3^v	3.347 (3)
Br1···H2^i	3.1900	C16···O4^vi	3.351 (3)
O1···O2	2.309 (3)	C2···H11^iii	2.8100
O1···C8^iii	3.192 (3)	C3···H11^iii	2.8600
O2···O1	2.309 (3)	C4···H13^x	3.0000
O2···O4^iii	3.115 (3)	C5···H13^x	3.0200
O2···C7^iv	3.155 (4)	C9···H2	2.9500
O3···C16^v	3.347 (3)	C10···H2	2.5500
O3···O4^v	2.656 (2)	C11···H2	2.8300
O3···C7^ii	3.367 (4)	C12···H13^vii	3.0900
O3···C11	3.124 (3)	C13···H4^ii	3.0300
O3···O3^v	3.238 (2)	C15···H2	2.9000
O4···C9^vi	3.418 (3)	C15···H11^iii	3.0400
O4···C16^vi	3.351 (3)	C16···H11	3.0900
O4···O3^v	2.656 (2)	C16···H4O^v	2.7600
O4···O2^vii	3.115 (3)	H2···C9	2.9500
O2···H7B^iv	2.9000	H2···C10	2.5500
O2···H8	2.6100	H2···C11	2.8300
O2···H7A^iv	2.8500	H2···C15	2.9000
O3···H4O^v	1.8400	H2···Br1^ix	3.1900
O3···H15^vii	2.5600	H4···Br1^viii	2.9000
O3···H7B^ii	2.4200	H4···C13^viii	3.0300
O4···H8	2.2900	H4O···O3^v	1.8400
C1···C15	3.454 (3)	H4O···C16^v	2.7600
C2···C10	3.098 (4)	H4O···H4O^v	2.5600
C2···C15	3.314 (4)	H7A···H8^iii	2.5800
C3···C11^iii	3.597 (4)	H7A···O2^iv	2.8500
C5···C8^iii	3.505 (4)	H7B···O3^viii	2.4200
C6···C16^iii	3.548 (4)	H7B···O2^iv	2.9000
C7···O2^iv	3.155 (4)	H8···O2	2.6100
C7···O3^viii	3.367 (4)	H8···O4	2.2900
C8···O1^vii	3.192 (3)	H8···H7A^vii	2.5800
C8···C5^vii	3.505 (4)	H11···C2^vii	2.8100
C9···O4^vi	3.418 (3)	H11···C3^vii	2.8600
C10···C2	3.098 (4)	H11···C15^vii	3.0400
C11···C3^vii	3.597 (4)	H11···C16	3.0900
C11···O3	3.124 (3)	H13···C4^xi	3.0000
C12···Br1^ix	3.426 (2)	H13···C5^xi	3.0200
C15···C1	3.454 (3)	H13···C12^iii	3.0900
C15···C2	3.314 (4)	H15···O3^iii	2.5600
C5—O1—C7	106.5 (2)	Br1—C13—C14	118.97 (18)
C6—O2—C7	105.8 (2)	C13—C14—C15	118.8 (2)
C16—O4—H4O	109.00	C10—C15—C14	120.7 (2)
C2—C1—C8	125.4 (2)	O3—C16—C9	122.0 (2)
C6—C1—C8	119.6 (2)	O4—C16—C9	115.6 (2)
C2—C1—C6	114.9 (2)	O3—C16—O4	122.4 (2)
C1—C2—C3	120.9 (2)	C1—C2—H2	120.00
C2—C3—C4	122.2 (3)	C3—C2—H2	119.00
C3—C4—C5	116.8 (3)	C2—C3—H3	119.00
O1—C5—C4	128.9 (3)	C4—C3—H3	119.00
O1—C5—C6	109.6 (3)	C3—C4—H4	122.00
C4—C5—C6	121.5 (3)	C5—C4—H4	122.00
O2—C6—C5	109.7 (2)	O1—C7—H7A	110.00
C1—C6—C5	123.5 (3)	O1—C7—H7B	110.00
O2—C6—C1	126.8 (2)	O2—C7—H7A	110.00
O1—C7—O2	107.3 (3)	O2—C7—H7B	110.00
C1—C8—C9	128.7 (2)	H7A—C7—H7B	109.00
C8—C9—C10	124.6 (2)	C1—C8—H8	116.00
C10—C9—C16	116.6 (2)	C9—C8—H8	116.00
C8—C9—C16	118.9 (2)	C10—C11—H11	120.00
C9—C10—C15	119.2 (2)	C12—C11—H11	120.00
C11—C10—C15	119.2 (2)	C11—C12—H12	121.00
C9—C10—C11	121.5 (2)	C13—C12—H12	121.00
C10—C11—C12	120.7 (2)	C13—C14—H13	121.00
C11—C12—C13	118.7 (2)	C15—C14—H13	121.00
Br1—C13—C12	119.28 (16)	C10—C15—H15	120.00
C12—C13—C14	121.8 (2)	C14—C15—H15	120.00
C7—O1—C5—C4	−173.5 (3)	C4—C5—C6—C1	−2.2 (4)
C7—O1—C5—C6	7.5 (3)	C1—C8—C9—C10	−5.2 (4)
C5—O1—C7—O2	−10.8 (3)	C1—C8—C9—C16	173.7 (2)
C7—O2—C6—C1	176.5 (3)	C8—C9—C10—C11	109.9 (3)
C7—O2—C6—C5	−5.7 (3)	C8—C9—C10—C15	−66.5 (3)
C6—O2—C7—O1	10.2 (3)	C16—C9—C10—C11	−69.0 (3)
C6—C1—C2—C3	−3.0 (4)	C16—C9—C10—C15	114.5 (2)
C8—C1—C2—C3	179.1 (3)	C8—C9—C16—O3	−171.6 (2)
C2—C1—C6—O2	−178.3 (2)	C8—C9—C16—O4	7.7 (3)
C2—C1—C6—C5	4.2 (4)	C10—C9—C16—O3	7.5 (3)
C8—C1—C6—O2	−0.3 (4)	C10—C9—C16—O4	−173.3 (2)
C8—C1—C6—C5	−177.8 (2)	C9—C10—C11—C12	−173.0 (2)
C2—C1—C8—C9	−22.5 (4)	C15—C10—C11—C12	3.5 (4)
C6—C1—C8—C9	159.8 (3)	C9—C10—C15—C14	173.8 (2)
C1—C2—C3—C4	0.0 (4)	C11—C10—C15—C14	−2.8 (4)
C2—C3—C4—C5	2.1 (5)	C10—C11—C12—C13	−0.6 (4)
C3—C4—C5—O1	−180.0 (3)	C11—C12—C13—Br1	176.70 (18)
C3—C4—C5—C6	−1.1 (4)	C11—C12—C13—C14	−3.0 (4)
O1—C5—C6—O2	−1.1 (3)	Br1—C13—C14—C15	−176.03 (18)
O1—C5—C6—C1	176.9 (2)	C12—C13—C14—C15	3.7 (4)
C4—C5—C6—O2	179.8 (3)	C13—C14—C15—C10	−0.7 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y−1, z; (iii) x+1, y, z; (iv) −x+2, −y+1, −z; (v) −x, −y, −z; (vi) −x+1, −y, −z; (vii) x−1, y, z; (viii) x+1, y+1, z; (ix) −x+1, y+1/2, −z+1/2; (x) x, y+1, z; (xi) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3^v	0.82	1.84	2.656 (2)	175
C4—H4···Br1^viii	0.95	2.90	3.820 (3)	165
C7—H7B···O3^viii	0.99	2.42	3.367 (4)	160
C8—H8···O4	0.95	2.29	2.705 (3)	106
C15—H15···O3^iii	0.95	2.56	3.483 (3)	165

Symmetry codes: (iii) x+1, y, z; (v) −x, −y, −z; (viii) x+1, y+1, z.