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The title compound, C10H7NO3, has an almost planar molecule, forming hydrogen-bonded dimers via the carboxyl groups. These dimers are further connected by hydrogen bonds between the hydroxy groups of the benzene rings and the cyano N atoms into ribbons, which are arranged in layers. The H atom of the carboxyl group is disordered over two sites.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001480/nc6017sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001480/nc6017Isup2.hkl
Contains datablock I

CCDC reference: 263717

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.032
  • wR factor = 0.093
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C21 .. 6.14 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C21 ... 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: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON.

2-Cyano-3-(4-hydroxyphenyl)acrylic acid top
Crystal data top
C10H7NO3F(000) = 392
Mr = 189.17Dx = 1.473 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 508 reflections
a = 5.8182 (5) Åθ = 3.4–20.9°
b = 9.5061 (7) ŵ = 0.11 mm1
c = 15.461 (1) ÅT = 173 K
β = 93.890 (6)°Block, yellow
V = 853.15 (11) Å30.52 × 0.48 × 0.32 mm
Z = 4
Data collection top
Siemens CCD three-circle
diffractometer
1798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.7°, θmin = 2.5°
ω scansh = 77
12012 measured reflectionsk = 1211
1986 independent reflectionsl = 2020
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1987P]
where P = (Fo2 + 2Fc2)/3
1986 reflections(Δ/σ)max = 0.001
140 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

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*/UeqOcc. (<1)
C10.36384 (16)0.34541 (11)0.40666 (6)0.0224 (2)
H10.23260.37780.43410.027*
C20.38596 (16)0.20353 (10)0.40581 (6)0.0212 (2)
C210.56447 (16)0.12633 (10)0.36770 (6)0.0220 (2)
N220.70468 (16)0.05833 (9)0.33942 (6)0.0282 (2)
C30.21527 (16)0.11533 (11)0.44786 (6)0.0215 (2)
O310.23948 (13)0.01816 (8)0.43955 (5)0.0292 (2)
H310.145 (4)0.064 (3)0.4640 (16)0.031 (9)*0.63 (5)
O320.06156 (13)0.17290 (8)0.48825 (5)0.0294 (2)
H320.037 (9)0.121 (5)0.507 (3)0.043 (17)*0.37 (5)
C110.50261 (16)0.45659 (10)0.37358 (6)0.0216 (2)
C120.42791 (16)0.59532 (10)0.38627 (6)0.0230 (2)
H120.28900.61060.41380.028*
C130.55103 (17)0.70988 (10)0.35979 (7)0.0238 (2)
H130.49680.80280.36840.029*
C140.75632 (16)0.68712 (10)0.32025 (6)0.0222 (2)
O140.89012 (13)0.79352 (8)0.29448 (5)0.0301 (2)
H140.827 (3)0.8778 (18)0.3075 (11)0.049 (4)*
C150.83189 (17)0.55013 (11)0.30525 (7)0.0247 (2)
H150.96980.53550.27690.030*
C160.70733 (17)0.43630 (10)0.33137 (7)0.0244 (2)
H160.75970.34360.32090.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0212 (4)0.0218 (5)0.0246 (5)0.0021 (3)0.0048 (4)0.0006 (4)
C20.0211 (4)0.0200 (5)0.0230 (5)0.0035 (3)0.0041 (4)0.0008 (4)
C210.0245 (4)0.0181 (5)0.0236 (5)0.0049 (3)0.0027 (4)0.0022 (4)
N220.0291 (4)0.0215 (4)0.0349 (5)0.0015 (3)0.0089 (4)0.0010 (4)
C30.0218 (4)0.0196 (5)0.0234 (5)0.0031 (3)0.0033 (3)0.0003 (4)
O310.0304 (4)0.0187 (4)0.0395 (4)0.0054 (3)0.0108 (3)0.0029 (3)
O320.0276 (4)0.0253 (4)0.0366 (4)0.0067 (3)0.0131 (3)0.0023 (3)
C110.0220 (4)0.0184 (5)0.0246 (5)0.0024 (3)0.0041 (4)0.0003 (4)
C120.0223 (4)0.0208 (5)0.0267 (5)0.0002 (4)0.0063 (4)0.0020 (4)
C130.0260 (5)0.0171 (5)0.0287 (5)0.0005 (4)0.0060 (4)0.0023 (4)
C140.0244 (5)0.0186 (5)0.0239 (5)0.0043 (3)0.0045 (4)0.0001 (4)
O140.0331 (4)0.0186 (4)0.0403 (4)0.0063 (3)0.0153 (3)0.0008 (3)
C150.0227 (4)0.0205 (5)0.0322 (5)0.0010 (4)0.0101 (4)0.0009 (4)
C160.0243 (5)0.0178 (5)0.0318 (5)0.0005 (3)0.0074 (4)0.0009 (4)
Geometric parameters (Å, º) top
C1—C21.3551 (14)C11—C161.4097 (13)
C1—C111.4445 (13)C12—C131.3807 (14)
C1—H10.9500C12—H120.9500
C2—C211.4309 (13)C13—C141.3951 (13)
C2—C31.4831 (12)C13—H130.9500
C21—N221.1503 (14)C14—O141.3527 (11)
C3—O321.2510 (12)C14—C151.3989 (14)
C3—O311.2842 (13)O14—H140.910 (17)
O31—H310.81 (3)C15—C161.3781 (13)
O32—H320.83 (6)C15—H150.9500
C11—C121.4065 (13)C16—H160.9500
C2—C1—C11131.99 (9)C13—C12—H12119.1
C2—C1—H1114.0C11—C12—H12119.1
C11—C1—H1114.0C12—C13—C14118.98 (9)
C1—C2—C21125.92 (9)C12—C13—H13120.5
C1—C2—C3119.44 (9)C14—C13—H13120.5
C21—C2—C3114.64 (8)O14—C14—C13122.69 (9)
N22—C21—C2176.49 (10)O14—C14—C15116.97 (8)
O32—C3—O31124.69 (9)C13—C14—C15120.34 (9)
O32—C3—C2119.62 (9)C14—O14—H14110.1 (10)
O31—C3—C2115.69 (8)C16—C15—C14120.33 (9)
C3—O31—H31113.5 (16)C16—C15—H15119.8
C3—O32—H32117 (3)C14—C15—H15119.8
C12—C11—C16118.14 (9)C15—C16—C11120.39 (9)
C12—C11—C1116.82 (9)C15—C16—H16119.8
C16—C11—C1125.03 (9)C11—C16—H16119.8
C13—C12—C11121.79 (9)
C11—C1—C2—C211.06 (19)C1—C11—C12—C13177.92 (9)
C11—C1—C2—C3178.44 (10)C11—C12—C13—C140.72 (16)
C1—C2—C3—O324.46 (14)C12—C13—C14—O14178.24 (9)
C21—C2—C3—O32175.10 (9)C12—C13—C14—C152.04 (16)
C1—C2—C3—O31175.75 (9)O14—C14—C15—C16178.61 (10)
C21—C2—C3—O314.70 (13)C13—C14—C15—C161.66 (16)
C2—C1—C11—C12179.77 (11)C14—C15—C16—C110.08 (16)
C2—C1—C11—C160.96 (18)C12—C11—C16—C151.37 (16)
C16—C11—C12—C130.97 (16)C1—C11—C16—C15177.43 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N22i0.910 (17)1.934 (17)2.8435 (12)177.2 (15)
O31—H31···O32ii0.81 (3)1.79 (3)2.5967 (10)176 (2)
O32—H32···O31ii0.83 (6)1.77 (6)2.5967 (10)173 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y, z+1.
 

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