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organic compounds
The asymmetric unit of the title compound, C13H10O3, contains two molecules with small conformational differences. Both molecules form hydrogen-bonded inversion dimers through their carboxyl groups.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008811/hb2299sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008811/hb2299Isup2.hkl |
CCDC reference: 642999
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.121
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 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 0 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 top
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
3-(2-Furyl)-2-phenylpropenoic acid top
Crystal data top
C13H10O3 | F(000) = 896 |
Mr = 214.21 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9612 reflections |
a = 8.682 (1) Å | θ = 2.7–27.5° |
b = 23.961 (5) Å | µ = 0.09 mm−1 |
c = 10.939 (2) Å | T = 173 K |
β = 106.603 (13)° | Prism, yellow |
V = 2180.8 (7) Å3 | 0.24 × 0.20 × 0.14 mm |
Z = 8 |
Data collection top
Nonius KappaCCD area-detector diffractometer | 4988 independent reflections |
Radiation source: fine-focus sealed tube | 3286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω and φ scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −11→11 |
Tmin = 0.978, Tmax = 0.987 | k = −31→31 |
9612 measured reflections | l = −14→14 |
Refinement top
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3 |
4988 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.59849 (12) | −0.06423 (5) | 0.05840 (9) | 0.0369 (3) | |
H1 | 0.5237 | −0.0877 | 0.0370 | 0.055* | |
O2 | 0.45887 (12) | −0.03655 (5) | 0.19068 (9) | 0.0382 (3) | |
O3 | 1.09393 (12) | 0.03541 (4) | 0.14457 (9) | 0.0379 (3) | |
O4 | 0.29077 (12) | 0.39610 (5) | 0.39287 (9) | 0.0428 (3) | |
H4 | 0.2128 | 0.4181 | 0.3671 | 0.064* | |
O5 | 0.13082 (11) | 0.35961 (4) | 0.50011 (9) | 0.0343 (3) | |
O6 | 0.82164 (11) | 0.31652 (4) | 0.58469 (9) | 0.0334 (3) | |
C1 | 0.57871 (17) | −0.03296 (6) | 0.15256 (12) | 0.0283 (3) | |
C2 | 0.71054 (16) | 0.00633 (6) | 0.21021 (12) | 0.0283 (3) | |
C3 | 0.83942 (16) | 0.00890 (6) | 0.16390 (12) | 0.0304 (3) | |
H3 | 0.8340 | −0.0132 | 0.0907 | 0.036* | |
C4 | 0.98296 (17) | 0.04113 (6) | 0.21263 (13) | 0.0307 (3) | |
C5 | 1.04663 (17) | 0.07521 (6) | 0.31433 (13) | 0.0338 (4) | |
H5 | 0.9963 | 0.0862 | 0.3771 | 0.041* | |
C6 | 1.20152 (18) | 0.09125 (7) | 0.30910 (14) | 0.0366 (4) | |
H6 | 1.2751 | 0.1149 | 0.3673 | 0.044* | |
C7 | 1.22369 (18) | 0.06638 (7) | 0.20576 (14) | 0.0376 (4) | |
H7 | 1.3180 | 0.0700 | 0.1789 | 0.045* | |
C8 | 0.69181 (16) | 0.03946 (6) | 0.32043 (12) | 0.0287 (3) | |
C9 | 0.7020 (2) | 0.01383 (7) | 0.43590 (14) | 0.0464 (4) | |
H9 | 0.7199 | −0.0253 | 0.4445 | 0.056* | |
C10 | 0.6865 (3) | 0.04461 (8) | 0.53923 (15) | 0.0572 (5) | |
H10 | 0.6936 | 0.0265 | 0.6179 | 0.069* | |
C11 | 0.6607 (2) | 0.10113 (7) | 0.52785 (14) | 0.0460 (4) | |
H11 | 0.6522 | 0.1222 | 0.5991 | 0.055* | |
C12 | 0.64736 (19) | 0.12716 (7) | 0.41336 (14) | 0.0403 (4) | |
H12 | 0.6276 | 0.1662 | 0.4049 | 0.048* | |
C13 | 0.66273 (18) | 0.09642 (7) | 0.31020 (13) | 0.0347 (4) | |
H13 | 0.6532 | 0.1146 | 0.2313 | 0.042* | |
C14 | 0.25897 (17) | 0.36011 (6) | 0.47275 (12) | 0.0284 (3) | |
C15 | 0.38742 (16) | 0.32002 (6) | 0.53086 (12) | 0.0279 (3) | |
C16 | 0.53867 (17) | 0.32891 (6) | 0.52708 (12) | 0.0296 (3) | |
H16 | 0.5568 | 0.3603 | 0.4801 | 0.035* | |
C17 | 0.67572 (16) | 0.29488 (6) | 0.58824 (12) | 0.0284 (3) | |
C18 | 0.70202 (18) | 0.24557 (7) | 0.65216 (14) | 0.0367 (4) | |
H18 | 0.6225 | 0.2219 | 0.6687 | 0.044* | |
C19 | 0.86914 (18) | 0.23609 (7) | 0.68943 (14) | 0.0392 (4) | |
H19 | 0.9237 | 0.2049 | 0.7356 | 0.047* | |
C20 | 0.93609 (18) | 0.27964 (7) | 0.64721 (13) | 0.0355 (4) | |
H20 | 1.0482 | 0.2841 | 0.6593 | 0.043* | |
C21 | 0.34280 (16) | 0.27277 (6) | 0.60277 (13) | 0.0286 (3) | |
C22 | 0.37532 (18) | 0.27588 (7) | 0.73456 (13) | 0.0367 (4) | |
H22 | 0.4213 | 0.3089 | 0.7780 | 0.044* | |
C23 | 0.3414 (2) | 0.23136 (8) | 0.80309 (15) | 0.0466 (4) | |
H23 | 0.3643 | 0.2339 | 0.8932 | 0.056* | |
C24 | 0.2749 (2) | 0.18359 (8) | 0.74119 (18) | 0.0501 (5) | |
H24 | 0.2525 | 0.1529 | 0.7884 | 0.060* | |
C25 | 0.2404 (2) | 0.18015 (8) | 0.60995 (18) | 0.0503 (5) | |
H25 | 0.1936 | 0.1471 | 0.5671 | 0.060* | |
C26 | 0.27379 (19) | 0.22473 (7) | 0.54041 (15) | 0.0393 (4) | |
H26 | 0.2493 | 0.2222 | 0.4502 | 0.047* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0375 (6) | 0.0384 (7) | 0.0373 (6) | −0.0113 (5) | 0.0147 (5) | −0.0131 (5) |
O2 | 0.0347 (6) | 0.0406 (7) | 0.0418 (6) | −0.0079 (5) | 0.0151 (5) | −0.0125 (5) |
O3 | 0.0354 (6) | 0.0377 (7) | 0.0450 (6) | −0.0049 (5) | 0.0187 (5) | −0.0048 (5) |
O4 | 0.0390 (7) | 0.0471 (8) | 0.0468 (6) | 0.0148 (5) | 0.0199 (5) | 0.0213 (5) |
O5 | 0.0307 (6) | 0.0362 (7) | 0.0372 (6) | 0.0065 (5) | 0.0116 (4) | 0.0087 (5) |
O6 | 0.0283 (6) | 0.0353 (6) | 0.0381 (6) | 0.0010 (5) | 0.0121 (4) | 0.0006 (4) |
C1 | 0.0312 (8) | 0.0273 (8) | 0.0266 (7) | 0.0001 (6) | 0.0086 (6) | −0.0010 (6) |
C2 | 0.0302 (8) | 0.0259 (8) | 0.0272 (7) | −0.0017 (6) | 0.0055 (6) | 0.0015 (6) |
C3 | 0.0334 (8) | 0.0290 (9) | 0.0281 (7) | −0.0017 (6) | 0.0078 (6) | −0.0014 (6) |
C4 | 0.0301 (8) | 0.0314 (9) | 0.0325 (7) | 0.0004 (7) | 0.0118 (6) | 0.0013 (6) |
C5 | 0.0326 (8) | 0.0356 (9) | 0.0331 (8) | −0.0007 (7) | 0.0093 (6) | −0.0022 (6) |
C6 | 0.0308 (8) | 0.0344 (9) | 0.0416 (8) | −0.0031 (7) | 0.0055 (7) | 0.0012 (7) |
C7 | 0.0290 (8) | 0.0333 (9) | 0.0518 (9) | −0.0045 (7) | 0.0138 (7) | 0.0039 (7) |
C8 | 0.0290 (7) | 0.0292 (9) | 0.0266 (7) | −0.0036 (6) | 0.0057 (6) | −0.0013 (6) |
C9 | 0.0769 (13) | 0.0296 (9) | 0.0336 (8) | 0.0016 (9) | 0.0170 (8) | 0.0006 (7) |
C10 | 0.0992 (15) | 0.0428 (12) | 0.0325 (9) | 0.0032 (11) | 0.0234 (9) | 0.0031 (8) |
C11 | 0.0675 (12) | 0.0404 (11) | 0.0329 (8) | 0.0009 (9) | 0.0190 (8) | −0.0081 (7) |
C12 | 0.0506 (10) | 0.0295 (9) | 0.0420 (9) | 0.0034 (7) | 0.0154 (7) | −0.0017 (7) |
C13 | 0.0421 (9) | 0.0328 (9) | 0.0296 (7) | 0.0008 (7) | 0.0111 (6) | 0.0027 (6) |
C14 | 0.0308 (8) | 0.0301 (9) | 0.0249 (7) | 0.0014 (6) | 0.0089 (6) | 0.0008 (6) |
C15 | 0.0279 (8) | 0.0309 (8) | 0.0247 (7) | 0.0031 (6) | 0.0072 (5) | −0.0004 (6) |
C16 | 0.0342 (8) | 0.0287 (8) | 0.0275 (7) | 0.0020 (6) | 0.0115 (6) | −0.0005 (6) |
C17 | 0.0265 (8) | 0.0293 (8) | 0.0318 (7) | −0.0007 (6) | 0.0121 (6) | −0.0033 (6) |
C18 | 0.0312 (8) | 0.0342 (9) | 0.0473 (9) | 0.0034 (7) | 0.0153 (7) | 0.0043 (7) |
C19 | 0.0331 (9) | 0.0429 (10) | 0.0411 (9) | 0.0097 (7) | 0.0100 (7) | 0.0079 (7) |
C20 | 0.0269 (8) | 0.0429 (10) | 0.0354 (8) | 0.0059 (7) | 0.0070 (6) | −0.0018 (7) |
C21 | 0.0229 (7) | 0.0313 (9) | 0.0316 (7) | 0.0066 (6) | 0.0076 (6) | 0.0047 (6) |
C22 | 0.0337 (8) | 0.0440 (10) | 0.0319 (8) | 0.0023 (7) | 0.0084 (6) | 0.0031 (7) |
C23 | 0.0440 (10) | 0.0583 (13) | 0.0384 (9) | 0.0068 (9) | 0.0134 (7) | 0.0173 (8) |
C24 | 0.0463 (10) | 0.0437 (11) | 0.0658 (12) | 0.0103 (9) | 0.0249 (8) | 0.0243 (9) |
C25 | 0.0560 (11) | 0.0319 (10) | 0.0677 (12) | −0.0040 (8) | 0.0255 (9) | −0.0005 (8) |
C26 | 0.0441 (9) | 0.0344 (10) | 0.0405 (8) | −0.0011 (8) | 0.0140 (7) | −0.0035 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.3240 (16) | C11—C12 | 1.374 (2) |
O1—H1 | 0.8400 | C11—H11 | 0.9500 |
O2—C1 | 1.2295 (16) | C12—C13 | 1.386 (2) |
O3—C7 | 1.3554 (18) | C12—H12 | 0.9500 |
O3—C4 | 1.3825 (16) | C13—H13 | 0.9500 |
O4—C14 | 1.3121 (16) | C14—C15 | 1.471 (2) |
O4—H4 | 0.8400 | C15—C16 | 1.343 (2) |
O5—C14 | 1.2320 (16) | C15—C21 | 1.492 (2) |
O6—C20 | 1.3592 (17) | C16—C17 | 1.440 (2) |
O6—C17 | 1.3796 (16) | C16—H16 | 0.9500 |
C1—C2 | 1.477 (2) | C17—C18 | 1.359 (2) |
C2—C3 | 1.3552 (18) | C18—C19 | 1.409 (2) |
C2—C8 | 1.4907 (19) | C18—H18 | 0.9500 |
C3—C4 | 1.433 (2) | C19—C20 | 1.339 (2) |
C3—H3 | 0.9500 | C19—H19 | 0.9500 |
C4—C5 | 1.363 (2) | C20—H20 | 0.9500 |
C5—C6 | 1.415 (2) | C21—C26 | 1.384 (2) |
C5—H5 | 0.9500 | C21—C22 | 1.390 (2) |
C6—C7 | 1.340 (2) | C22—C23 | 1.383 (2) |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C7—H7 | 0.9500 | C23—C24 | 1.371 (3) |
C8—C9 | 1.384 (2) | C23—H23 | 0.9500 |
C8—C13 | 1.387 (2) | C24—C25 | 1.383 (3) |
C9—C10 | 1.388 (2) | C24—H24 | 0.9500 |
C9—H9 | 0.9500 | C25—C26 | 1.389 (2) |
C10—C11 | 1.372 (3) | C25—H25 | 0.9500 |
C10—H10 | 0.9500 | C26—H26 | 0.9500 |
C1—O1—H1 | 109.5 | C12—C13—H13 | 119.5 |
C7—O3—C4 | 106.77 (11) | C8—C13—H13 | 119.5 |
C14—O4—H4 | 109.5 | O5—C14—O4 | 123.00 (13) |
C20—O6—C17 | 106.67 (12) | O5—C14—C15 | 120.95 (12) |
O2—C1—O1 | 122.33 (13) | O4—C14—C15 | 116.04 (12) |
O2—C1—C2 | 121.83 (12) | C16—C15—C14 | 120.69 (13) |
O1—C1—C2 | 115.84 (12) | C16—C15—C21 | 122.71 (13) |
C3—C2—C1 | 119.42 (12) | C14—C15—C21 | 116.37 (12) |
C3—C2—C8 | 124.80 (13) | C15—C16—C17 | 125.56 (14) |
C1—C2—C8 | 115.75 (12) | C15—C16—H16 | 117.2 |
C2—C3—C4 | 127.48 (13) | C17—C16—H16 | 117.2 |
C2—C3—H3 | 116.3 | C18—C17—O6 | 108.70 (12) |
C4—C3—H3 | 116.3 | C18—C17—C16 | 136.60 (14) |
C5—C4—O3 | 108.44 (12) | O6—C17—C16 | 114.69 (12) |
C5—C4—C3 | 137.15 (14) | C17—C18—C19 | 107.27 (14) |
O3—C4—C3 | 114.33 (12) | C17—C18—H18 | 126.4 |
C4—C5—C6 | 107.34 (13) | C19—C18—H18 | 126.4 |
C4—C5—H5 | 126.3 | C20—C19—C18 | 106.69 (14) |
C6—C5—H5 | 126.3 | C20—C19—H19 | 126.7 |
C7—C6—C5 | 106.29 (14) | C18—C19—H19 | 126.7 |
C7—C6—H6 | 126.9 | C19—C20—O6 | 110.68 (13) |
C5—C6—H6 | 126.9 | C19—C20—H20 | 124.7 |
C6—C7—O3 | 111.14 (13) | O6—C20—H20 | 124.7 |
C6—C7—H7 | 124.4 | C26—C21—C22 | 119.13 (14) |
O3—C7—H7 | 124.4 | C26—C21—C15 | 120.83 (13) |
C9—C8—C13 | 118.22 (13) | C22—C21—C15 | 120.01 (14) |
C9—C8—C2 | 120.56 (14) | C23—C22—C21 | 120.63 (16) |
C13—C8—C2 | 121.22 (12) | C23—C22—H22 | 119.7 |
C8—C9—C10 | 120.77 (16) | C21—C22—H22 | 119.7 |
C8—C9—H9 | 119.6 | C24—C23—C22 | 120.08 (15) |
C10—C9—H9 | 119.6 | C24—C23—H23 | 120.0 |
C11—C10—C9 | 120.10 (15) | C22—C23—H23 | 120.0 |
C11—C10—H10 | 120.0 | C23—C24—C25 | 119.90 (16) |
C9—C10—H10 | 120.0 | C23—C24—H24 | 120.0 |
C10—C11—C12 | 119.99 (15) | C25—C24—H24 | 120.0 |
C10—C11—H11 | 120.0 | C24—C25—C26 | 120.36 (17) |
C12—C11—H11 | 120.0 | C24—C25—H25 | 119.8 |
C11—C12—C13 | 119.88 (16) | C26—C25—H25 | 119.8 |
C11—C12—H12 | 120.1 | C21—C26—C25 | 119.89 (15) |
C13—C12—H12 | 120.1 | C21—C26—H26 | 120.1 |
C12—C13—C8 | 121.01 (13) | C25—C26—H26 | 120.1 |
O2—C1—C2—C3 | −179.50 (13) | O5—C14—C15—C16 | −163.10 (13) |
O1—C1—C2—C3 | 1.05 (19) | O4—C14—C15—C16 | 16.01 (19) |
O2—C1—C2—C8 | 2.4 (2) | O5—C14—C15—C21 | 11.60 (19) |
O1—C1—C2—C8 | −177.06 (12) | O4—C14—C15—C21 | −169.29 (13) |
C1—C2—C3—C4 | −175.18 (14) | C14—C15—C16—C17 | 175.29 (13) |
C8—C2—C3—C4 | 2.8 (2) | C21—C15—C16—C17 | 0.9 (2) |
C7—O3—C4—C5 | −0.25 (16) | C20—O6—C17—C18 | 0.01 (15) |
C7—O3—C4—C3 | −177.47 (12) | C20—O6—C17—C16 | 179.40 (11) |
C2—C3—C4—C5 | 4.1 (3) | C15—C16—C17—C18 | 7.3 (3) |
C2—C3—C4—O3 | −179.74 (14) | C15—C16—C17—O6 | −171.85 (12) |
O3—C4—C5—C6 | 0.16 (16) | O6—C17—C18—C19 | −0.09 (16) |
C3—C4—C5—C6 | 176.43 (17) | C16—C17—C18—C19 | −179.29 (16) |
C4—C5—C6—C7 | −0.01 (17) | C17—C18—C19—C20 | 0.14 (18) |
C5—C6—C7—O3 | −0.15 (17) | C18—C19—C20—O6 | −0.14 (18) |
C4—O3—C7—C6 | 0.25 (17) | C17—O6—C20—C19 | 0.09 (16) |
C3—C2—C8—C9 | −108.70 (18) | C16—C15—C21—C26 | −100.31 (17) |
C1—C2—C8—C9 | 69.30 (18) | C14—C15—C21—C26 | 85.11 (17) |
C3—C2—C8—C13 | 71.74 (19) | C16—C15—C21—C22 | 77.53 (18) |
C1—C2—C8—C13 | −110.26 (16) | C14—C15—C21—C22 | −97.06 (16) |
C13—C8—C9—C10 | −1.1 (2) | C26—C21—C22—C23 | 0.9 (2) |
C2—C8—C9—C10 | 179.28 (16) | C15—C21—C22—C23 | −176.98 (13) |
C8—C9—C10—C11 | −0.1 (3) | C21—C22—C23—C24 | −0.1 (2) |
C9—C10—C11—C12 | 1.2 (3) | C22—C23—C24—C25 | −0.6 (3) |
C10—C11—C12—C13 | −1.2 (3) | C23—C24—C25—C26 | 0.4 (3) |
C11—C12—C13—C8 | −0.1 (2) | C22—C21—C26—C25 | −1.0 (2) |
C9—C8—C13—C12 | 1.2 (2) | C15—C21—C26—C25 | 176.84 (14) |
C2—C8—C13—C12 | −179.20 (13) | C24—C25—C26—C21 | 0.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5i | 0.84 | 1.80 | 2.6410 (14) | 177 |
O4—H4···O2ii | 0.84 | 1.81 | 2.6467 (15) | 178 |
C13—H13···O5iii | 0.95 | 2.56 | 3.4866 (18) | 167 |
C23—H23···O6iv | 0.95 | 2.54 | 3.3372 (19) | 142 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) x−1/2, −y+1/2, z+1/2. |
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