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

In the solid-state structure of the title compound, C₁₆H₁₁NO₄, the double bond is E, and the mean planes through the two aromatic rings are inclined to one another by 64.81 (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...O and C—H...F inter­molecular hydrogen bonds, leading to the formation of a slab-like structure, two mol­ecules thick, extending in the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count < 85% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           26.14
           From the CIF: _diffrn_reflns_theta_full          26.14
           From the CIF: _reflns_number_total               2213
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2606
           Completeness (_total/calc)             84.92%

Author Response: ...see _publ_section_exptl_refinement

PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.85

Author Response: ...see _publ_section_exptl_refinement

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.85

Author Response: ...see _publ_section_exptl_refinement

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: TWIN-INTEGRATE (Stoe & Cie, 2000); 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-fluorophenyl)acrylic acid

Crystal data

C16H11FO4	Z = 2
Mr = 286.25	F(000) = 296
Triclinic, P1	Dx = 1.455 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6894 (12) Å	Cell parameters from 2432 reflections
b = 8.3041 (19) Å	θ = 2.5–25.9°
c = 13.959 (3) Å	µ = 0.11 mm^−1
α = 97.29 (3)°	T = 173 K
β = 92.52 (2)°	Plate, pale yellow
γ = 90.10 (3)°	0.30 × 0.23 × 0.08 mm
V = 653.5 (2) Å^3

Data collection

Stoe IPDS diffractometer	1219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 26.1°, θmin = 2.5°
Detector resolution: 0.81Å pixels mm^-1	h = −6→6
φ scans	k = −10→10
4576 measured reflections	l = −17→17
2213 independent 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0694P)^2] where P = (Fo^2 + 2Fc^2)/3
2213 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.19 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
F1	0.5432 (3)	−0.2869 (2)	0.47285 (10)	0.0521 (6)
O1	1.2812 (4)	0.5381 (3)	0.20678 (13)	0.0538 (8)
O2	0.9705 (4)	0.4257 (2)	0.10647 (12)	0.0490 (7)
O3	0.1146 (3)	−0.0585 (2)	0.09853 (11)	0.0393 (6)
O4	0.2633 (4)	0.1316 (2)	0.01775 (12)	0.0414 (7)
C1	0.7745 (5)	0.2920 (3)	0.22963 (16)	0.0325 (8)
C2	0.7897 (5)	0.2786 (3)	0.33027 (16)	0.0367 (9)
C3	0.9703 (5)	0.3499 (3)	0.38984 (17)	0.0401 (10)
C4	1.1497 (5)	0.4385 (3)	0.35415 (17)	0.0409 (10)
C5	1.1308 (5)	0.4567 (3)	0.25872 (18)	0.0389 (10)
C6	0.9465 (5)	0.3881 (3)	0.19940 (16)	0.0334 (9)
C7	1.1662 (6)	0.5371 (4)	0.1127 (2)	0.0566 (13)
C8	0.5924 (5)	0.2182 (3)	0.16090 (16)	0.0337 (8)
C9	0.4516 (4)	0.0900 (3)	0.16767 (15)	0.0300 (8)
C10	0.4694 (4)	−0.0152 (3)	0.24676 (15)	0.0304 (8)
C11	0.2959 (5)	−0.0143 (3)	0.31421 (16)	0.0370 (9)
C12	0.3215 (5)	−0.1047 (3)	0.39079 (16)	0.0402 (10)
C13	0.5177 (5)	−0.1971 (3)	0.39772 (16)	0.0374 (9)
C14	0.6910 (5)	−0.2061 (3)	0.33117 (17)	0.0395 (9)
C15	0.6648 (5)	−0.1134 (3)	0.25561 (17)	0.0377 (9)
C16	0.2627 (5)	0.0470 (3)	0.09198 (16)	0.0314 (8)
H2	0.67200	0.21890	0.35710	0.0440*
H3	0.97350	0.33880	0.45680	0.0480*
H4	1.27820	0.48350	0.39470	0.0490*
H4O	0.142 (4)	0.105 (4)	−0.0206 (19)	0.060 (10)*
H7A	1.11010	0.64740	0.10400	0.0680*
H7B	1.27720	0.50210	0.06160	0.0680*
H8	0.57000	0.26760	0.10340	0.0400*
H11	0.15850	0.04900	0.30760	0.0440*
H12	0.20470	−0.10240	0.43750	0.0480*
H14	0.82420	−0.27360	0.33700	0.0470*
H15	0.78220	−0.11710	0.20910	0.0450*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0566 (12)	0.0654 (11)	0.0361 (8)	−0.0083 (8)	−0.0105 (7)	0.0176 (7)
O1	0.0518 (16)	0.0597 (14)	0.0496 (11)	−0.0234 (11)	−0.0084 (9)	0.0102 (9)
O2	0.0569 (15)	0.0564 (13)	0.0345 (9)	−0.0192 (10)	−0.0036 (8)	0.0107 (8)
O3	0.0354 (12)	0.0495 (12)	0.0334 (9)	−0.0122 (9)	−0.0113 (7)	0.0112 (8)
O4	0.0412 (14)	0.0489 (12)	0.0342 (10)	−0.0111 (10)	−0.0135 (8)	0.0116 (8)
C1	0.0285 (16)	0.0351 (15)	0.0319 (13)	0.0010 (11)	−0.0035 (10)	−0.0022 (10)
C2	0.0360 (18)	0.0453 (17)	0.0272 (12)	−0.0037 (13)	−0.0006 (10)	−0.0003 (10)
C3	0.045 (2)	0.0447 (17)	0.0284 (12)	−0.0002 (13)	−0.0067 (11)	−0.0011 (11)
C4	0.0409 (19)	0.0413 (17)	0.0378 (14)	−0.0059 (13)	−0.0139 (11)	−0.0002 (11)
C5	0.0365 (19)	0.0364 (16)	0.0427 (14)	−0.0060 (12)	−0.0016 (12)	0.0015 (11)
C6	0.0349 (18)	0.0350 (15)	0.0292 (12)	−0.0010 (12)	−0.0053 (10)	0.0023 (10)
C7	0.066 (3)	0.057 (2)	0.0477 (17)	−0.0209 (17)	−0.0075 (15)	0.0141 (14)
C8	0.0304 (16)	0.0400 (15)	0.0295 (12)	0.0036 (12)	−0.0018 (10)	0.0009 (10)
C9	0.0281 (16)	0.0345 (14)	0.0259 (12)	0.0001 (12)	−0.0026 (10)	−0.0010 (10)
C10	0.0221 (16)	0.0410 (15)	0.0264 (12)	−0.0016 (11)	−0.0044 (9)	−0.0003 (10)
C11	0.0276 (17)	0.0505 (17)	0.0318 (13)	0.0038 (12)	−0.0005 (10)	0.0017 (11)
C12	0.0341 (18)	0.0579 (19)	0.0285 (13)	−0.0065 (14)	0.0020 (11)	0.0050 (12)
C13	0.0397 (19)	0.0454 (17)	0.0272 (12)	−0.0086 (13)	−0.0101 (11)	0.0092 (11)
C14	0.0320 (18)	0.0471 (17)	0.0396 (14)	0.0061 (13)	−0.0057 (11)	0.0082 (12)
C15	0.0300 (17)	0.0508 (17)	0.0317 (13)	0.0002 (13)	−0.0007 (10)	0.0041 (11)
C16	0.0282 (16)	0.0384 (15)	0.0266 (12)	0.0024 (12)	−0.0022 (10)	0.0016 (10)

Geometric parameters (Å, º)

F1—C13	1.365 (3)	C9—C16	1.484 (3)
O1—C5	1.375 (3)	C10—C15	1.390 (4)
O1—C7	1.440 (3)	C10—C11	1.393 (3)
O2—C6	1.385 (3)	C11—C12	1.385 (3)
O2—C7	1.439 (4)	C12—C13	1.363 (4)
O3—C16	1.229 (3)	C13—C14	1.380 (4)
O4—C16	1.324 (3)	C14—C15	1.386 (3)
O4—H4O	0.87 (2)	C2—H2	0.9500
C1—C2	1.422 (3)	C3—H3	0.9500
C1—C8	1.460 (4)	C4—H4	0.9500
C1—C6	1.375 (4)	C7—H7A	0.9900
C2—C3	1.377 (4)	C7—H7B	0.9900
C3—C4	1.402 (4)	C8—H8	0.9500
C4—C5	1.359 (3)	C11—H11	0.9500
C5—C6	1.383 (4)	C12—H12	0.9500
C8—C9	1.347 (4)	C14—H14	0.9500
C9—C10	1.493 (3)	C15—H15	0.9500
F1···C4^i	3.298 (3)	C15···C2	3.355 (4)
F1···H4^ii	2.5300	C15···C1	3.490 (4)
F1···H2^iii	2.7100	C16···C6^ix	3.562 (4)
F1···H4^i	2.7800	C16···O3^vii	3.354 (3)
O1···O2	2.324 (3)	C16···O4^viii	3.409 (3)
O1···C8^iv	3.207 (4)	C2···H11^iv	2.8400
O1···C14^v	3.414 (4)	C3···H11^iv	2.8500
O2···O1	2.324 (3)	C4···H14^x	3.0500
O2···O4^iv	3.115 (3)	C5···H14^x	2.9700
O2···C7^vi	3.177 (3)	C9···H2	2.9500
O3···O4^vii	2.658 (3)	C10···H2	2.5600
O3···C16^vii	3.354 (3)	C11···H2	2.8800
O3···C7^ii	3.401 (4)	C13···H4^ii	2.9700
O3···C11	3.116 (3)	C15···H2	2.9400
O4···O3^vii	2.658 (3)	C16···H11	3.0900
O4···C16^viii	3.409 (3)	C16···H4O^vii	2.71 (3)
O4···O2^ix	3.115 (3)	H2···C9	2.9500
O2···H7B^vi	2.8100	H2···C10	2.5600
O2···H8	2.6200	H2···C11	2.8800
O3···H4O^vii	1.79 (2)	H2···C15	2.9400
O3···H7A^ii	2.4500	H2···F1^iii	2.7100
O3···H15^ix	2.5800	H4···F1^v	2.5300
O4···H8	2.2800	H4···C13^v	2.9700
C1···C15	3.490 (4)	H4···F1^i	2.7800
C2···C10	3.116 (4)	H4O···O3^vii	1.79 (2)
C2···C15	3.355 (4)	H4O···C16^vii	2.71 (3)
C4···F1^i	3.298 (3)	H4O···H4O^vii	2.51 (4)
C5···C8^iv	3.512 (4)	H7A···O3^v	2.4500
C6···C16^iv	3.562 (4)	H7B···O2^vi	2.8100
C7···C7^vi	3.583 (4)	H8···O2	2.6200
C7···O2^vi	3.177 (3)	H8···O4	2.2800
C7···O3^v	3.401 (4)	H11···C2^ix	2.8400
C8···C5^ix	3.512 (4)	H11···C3^ix	2.8500
C8···O1^ix	3.207 (4)	H11···C16	3.0900
C10···C2	3.116 (4)	H14···C4^xi	3.0500
C11···O3	3.116 (3)	H14···C5^xi	2.9700
C14···O1^ii	3.414 (4)	H15···O3^iv	2.5800
C5—O1—C7	105.5 (2)	F1—C13—C14	118.3 (2)
C6—O2—C7	105.7 (2)	C13—C14—C15	117.9 (2)
C16—O4—H4O	110 (2)	C10—C15—C14	121.1 (2)
C2—C1—C8	125.5 (2)	O3—C16—C9	122.2 (2)
C6—C1—C8	120.2 (2)	O4—C16—C9	115.3 (2)
C2—C1—C6	114.3 (2)	O3—C16—O4	122.5 (2)
C1—C2—C3	121.8 (2)	C1—C2—H2	119.00
C2—C3—C4	121.6 (2)	C3—C2—H2	119.00
C3—C4—C5	116.7 (2)	C2—C3—H3	119.00
O1—C5—C4	128.0 (3)	C4—C3—H3	119.00
O1—C5—C6	110.4 (2)	C3—C4—H4	122.00
C4—C5—C6	121.6 (3)	C5—C4—H4	122.00
O2—C6—C5	109.5 (2)	O1—C7—H7A	110.00
C1—C6—C5	123.9 (2)	O1—C7—H7B	110.00
O2—C6—C1	126.6 (2)	O2—C7—H7A	110.00
O1—C7—O2	107.7 (2)	O2—C7—H7B	110.00
C1—C8—C9	129.0 (2)	H7A—C7—H7B	108.00
C8—C9—C10	124.9 (2)	C1—C8—H8	115.00
C10—C9—C16	116.1 (2)	C9—C8—H8	116.00
C8—C9—C16	119.0 (2)	C10—C11—H11	120.00
C9—C10—C15	120.0 (2)	C12—C11—H11	120.00
C11—C10—C15	118.8 (2)	C11—C12—H12	121.00
C9—C10—C11	121.3 (2)	C13—C12—H12	121.00
C10—C11—C12	120.7 (2)	C13—C14—H14	121.00
C11—C12—C13	118.6 (2)	C15—C14—H14	121.00
F1—C13—C12	118.8 (2)	C10—C15—H15	119.00
C12—C13—C14	122.9 (2)	C14—C15—H15	119.00
C7—O1—C5—C4	−173.3 (3)	C4—C5—C6—C1	−2.7 (4)
C7—O1—C5—C6	7.7 (3)	C1—C8—C9—C10	−5.8 (4)
C5—O1—C7—O2	−11.4 (3)	C1—C8—C9—C16	174.2 (3)
C7—O2—C6—C1	176.5 (3)	C8—C9—C10—C11	111.3 (3)
C7—O2—C6—C5	−6.2 (3)	C8—C9—C10—C15	−67.0 (3)
C6—O2—C7—O1	10.9 (3)	C16—C9—C10—C11	−68.7 (3)
C6—C1—C2—C3	−3.3 (4)	C16—C9—C10—C15	113.0 (3)
C8—C1—C2—C3	178.8 (3)	C8—C9—C16—O3	−173.0 (2)
C2—C1—C6—O2	−178.2 (2)	C8—C9—C16—O4	6.2 (3)
C2—C1—C6—C5	4.9 (4)	C10—C9—C16—O3	7.0 (3)
C8—C1—C6—O2	−0.1 (4)	C10—C9—C16—O4	−173.9 (2)
C8—C1—C6—C5	−177.1 (3)	C9—C10—C11—C12	−175.9 (2)
C2—C1—C8—C9	−22.1 (4)	C15—C10—C11—C12	2.4 (4)
C6—C1—C8—C9	160.1 (3)	C9—C10—C15—C14	176.8 (2)
C1—C2—C3—C4	−0.5 (4)	C11—C10—C15—C14	−1.6 (4)
C2—C3—C4—C5	2.9 (4)	C10—C11—C12—C13	−1.3 (4)
C3—C4—C5—O1	179.6 (3)	C11—C12—C13—F1	−179.7 (2)
C3—C4—C5—C6	−1.4 (4)	C11—C12—C13—C14	−0.8 (4)
O1—C5—C6—O2	−0.9 (3)	F1—C13—C14—C15	−179.4 (2)
O1—C5—C6—C1	176.5 (3)	C12—C13—C14—C15	1.6 (4)
C4—C5—C6—O2	179.9 (2)	C13—C14—C15—C10	−0.4 (4)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y−1, z; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) −x+2, −y+1, −z; (vii) −x, −y, −z; (viii) −x+1, −y, −z; (ix) x−1, y, z; (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^vii	0.87 (2)	1.79 (2)	2.658 (3)	178 (4)
C4—H4···F1^v	0.95	2.53	3.414 (3)	154
C7—H7A···O3^v	0.99	2.45	3.401 (4)	160
C8—H8···O4	0.95	2.28	2.705 (3)	106
C15—H15···O3^iv	0.95	2.58	3.508 (3)	167

Symmetry codes: (iv) x+1, y, z; (v) x+1, y+1, z; (vii) −x, −y, −z.