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The title compound, C10H7NO3, has the cyano, carboxyl­ic acid and phenol groups in a trans configuration with respect to the C=C double bond. Intramolecular O—H...N and eight-membered O—H...O hydrogen-bonding interactions form an infinite two-dimensional layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001224/ac6150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001224/ac6150Isup2.hkl
Contains datablock I

CCDC reference: 263712

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.115
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C4 .. 6.90 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Cyano-3-(4-hydroxyphenyl)propenoic acid top
Crystal data top
C10H7NO3F(000) = 392
Mr = 189.17Dx = 1.448 Mg m3
Monoclinic, P21/cMelting point = 250–252 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.839 (2) ÅCell parameters from 2966 reflections
b = 9.498 (3) Åθ = 3.4–27.5°
c = 15.663 (5) ŵ = 0.11 mm1
β = 92.76 (2)°T = 296 K
V = 867.6 (5) Å3Block, yellow
Z = 40.30 × 0.30 × 0.20 mm
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
1513 independent reflections
Radiation source: Rigaku rotating anode1415 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
Detector resolution: 14.6199 pixels mm-1θmax = 25.0°, θmin = 3.4°
φ and ω scansh = 66
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
k = 1011
Tmin = 0.969, Tmax = 0.977l = 1818
7176 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0104P)2 + 1.0945P]
where P = (Fo2 + 2Fc2)/3
1513 reflections(Δ/σ)max < 0.001
129 parametersΔρmax = 0.18 e Å3
6 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2142 (4)0.6175 (2)0.44789 (15)0.0364 (5)
C20.3832 (4)0.7070 (2)0.40645 (14)0.0344 (5)
C30.3631 (4)0.8481 (2)0.40723 (15)0.0367 (5)
H3A0.23470.87980.43440.044*
C40.5625 (4)0.6303 (2)0.36806 (15)0.0364 (5)
C50.5000 (4)0.9596 (2)0.37457 (15)0.0348 (5)
C60.4268 (4)1.0979 (2)0.38688 (15)0.0380 (6)
H60.29081.11310.41410.046*
C70.5482 (4)1.2115 (2)0.36033 (15)0.0395 (6)
H70.49491.30240.36910.047*
C80.7513 (4)1.1898 (2)0.32027 (15)0.0373 (6)
C90.8270 (4)1.0539 (2)0.30573 (16)0.0408 (6)
H90.96221.03960.27790.049*
C100.7043 (4)0.9406 (2)0.33206 (16)0.0405 (6)
H100.75660.85000.32170.049*
N10.7021 (4)0.5629 (2)0.33906 (14)0.0483 (6)
O10.2385 (3)0.48550 (17)0.44052 (12)0.0497 (5)
H1B0.13340.44510.46330.074*
O20.0579 (3)0.67546 (17)0.48836 (12)0.0493 (5)
O30.8849 (3)1.29617 (17)0.29371 (13)0.0525 (5)
H30.83041.37180.30790.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0385 (13)0.0311 (12)0.0397 (13)0.0053 (10)0.0027 (10)0.0002 (10)
C20.0340 (12)0.0321 (11)0.0375 (12)0.0055 (9)0.0069 (10)0.0001 (10)
C30.0358 (13)0.0332 (12)0.0414 (13)0.0041 (10)0.0070 (10)0.0003 (10)
C40.0396 (13)0.0306 (11)0.0394 (13)0.0114 (10)0.0044 (11)0.0049 (10)
C50.0355 (12)0.0287 (11)0.0404 (13)0.0040 (9)0.0043 (10)0.0013 (9)
C60.0353 (13)0.0365 (13)0.0430 (14)0.0001 (10)0.0090 (11)0.0028 (10)
C70.0431 (14)0.0281 (11)0.0480 (14)0.0001 (10)0.0102 (11)0.0033 (10)
C80.0426 (13)0.0298 (12)0.0399 (13)0.0086 (10)0.0059 (11)0.0017 (10)
C90.0374 (13)0.0333 (12)0.0533 (15)0.0019 (10)0.0173 (11)0.0002 (11)
C100.0394 (13)0.0290 (11)0.0541 (15)0.0010 (10)0.0115 (11)0.0008 (11)
N10.0506 (13)0.0347 (11)0.0610 (14)0.0025 (10)0.0175 (11)0.0006 (10)
O10.0472 (11)0.0325 (9)0.0710 (13)0.0102 (8)0.0207 (9)0.0045 (9)
O20.0461 (11)0.0397 (10)0.0639 (12)0.0089 (8)0.0227 (9)0.0048 (8)
O30.0597 (12)0.0303 (9)0.0698 (13)0.0099 (8)0.0262 (10)0.0009 (9)
Geometric parameters (Å, º) top
C1—O21.262 (3)C6—H60.9300
C1—O11.267 (3)C7—C81.383 (3)
C1—C21.477 (3)C7—H70.9300
C2—C31.346 (3)C8—O31.354 (3)
C2—C41.431 (3)C8—C91.387 (3)
C3—C51.435 (3)C9—C101.367 (3)
C3—H3A0.9300C9—H90.9300
C4—N11.147 (3)C10—H100.9300
C5—C61.398 (3)O1—H1B0.8200
C5—C101.406 (3)O3—H30.8200
C6—C71.367 (3)
O2—C1—O1124.3 (2)C5—C6—H6118.9
O2—C1—C2119.0 (2)C6—C7—C8119.3 (2)
O1—C1—C2116.7 (2)C6—C7—H7120.4
C3—C2—C4125.2 (2)C8—C7—H7120.4
C3—C2—C1120.6 (2)O3—C8—C7123.2 (2)
C4—C2—C1114.17 (19)O3—C8—C9116.8 (2)
C2—C3—C5132.9 (2)C7—C8—C9120.0 (2)
C2—C3—H3A113.5C10—C9—C8120.5 (2)
C5—C3—H3A113.5C10—C9—H9119.8
N1—C4—C2176.6 (2)C8—C9—H9119.8
C6—C5—C10117.2 (2)C9—C10—C5120.8 (2)
C6—C5—C3117.7 (2)C9—C10—H10119.6
C10—C5—C3125.1 (2)C5—C10—H10119.6
C7—C6—C5122.2 (2)C1—O1—H1B109.5
C7—C6—H6118.9C8—O3—H3109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.821.792.600 (2)168
O3—H3···N1ii0.822.032.853 (3)178
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z.
 

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