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In the solid-state structure of the title compound, C16H11NO6, the configuration about the C=C double bond is E, and the two aromatic rings are inclined to one another by 67.96 (7)°. 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 inter­molecular hydrogen bonds, leading to the formation of a sheet-like structure in the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040724/bx2031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040724/bx2031Isup2.hkl
Contains datablock I

CCDC reference: 627366

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.041
  • wR factor = 0.112
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED32 (Stoe & Cie, 2005); 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.

(I) top
Crystal data top
C16H11NO6F(000) = 648
Mr = 313.26Dx = 1.488 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11122 reflections
a = 8.8747 (6) Åθ = 2.0–29.5°
b = 15.4381 (13) ŵ = 0.12 mm1
c = 10.8315 (7) ÅT = 173 K
β = 109.529 (5)°Block, yellow
V = 1398.64 (18) Å30.50 × 0.40 × 0.22 mm
Z = 4
Data collection top
STOE IPDS-2
diffractometer
3019 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 29.2°, θmin = 2.4°
Detector resolution: 6.67 pixels mm-1h = 1212
ω & φ scansk = 2121
11303 measured reflectionsl = 1414
3714 independent 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.057P)2 + 0.310P]
where P = (Fo2 + 2Fc2)/3
3714 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.31588 (13)0.47351 (7)0.73562 (11)0.0480 (3)
O20.35207 (12)0.33506 (6)0.73484 (10)0.0427 (3)
O30.97768 (13)0.47056 (7)1.15601 (12)0.0503 (4)
O40.83611 (16)0.58879 (7)1.04460 (12)0.0546 (4)
O50.45495 (11)0.10331 (6)0.97796 (11)0.0400 (3)
O60.65627 (11)0.03382 (5)0.94141 (10)0.0347 (3)
N10.39740 (13)0.40832 (7)0.77520 (11)0.0332 (3)
C10.63546 (14)0.34706 (7)0.94186 (12)0.0261 (3)
C20.78489 (15)0.36028 (8)1.04008 (13)0.0316 (3)
C30.83898 (16)0.44361 (9)1.06524 (14)0.0359 (4)
C40.75419 (18)0.51397 (8)0.99691 (14)0.0378 (4)
C50.61165 (18)0.50454 (8)0.89915 (14)0.0364 (4)
C60.55371 (15)0.41921 (7)0.87450 (12)0.0285 (3)
C70.9668 (2)0.56348 (10)1.15806 (17)0.0507 (5)
C80.56910 (14)0.25852 (7)0.93176 (12)0.0264 (3)
C90.64469 (13)0.18610 (7)0.91706 (12)0.0252 (3)
C100.78835 (14)0.18626 (7)0.87578 (12)0.0281 (3)
C110.92924 (16)0.14410 (10)0.94660 (15)0.0407 (4)
C121.06315 (18)0.15095 (12)0.9077 (2)0.0564 (6)
C131.0568 (2)0.19803 (11)0.7981 (2)0.0601 (6)
C140.9166 (2)0.23751 (9)0.72511 (19)0.0533 (6)
C150.78200 (18)0.23191 (8)0.76348 (15)0.0379 (4)
C160.57775 (14)0.10303 (7)0.94604 (12)0.0276 (3)
H20.845900.312901.087200.0380*
H50.554800.552500.850600.0440*
H60.614700.008600.966500.0520*
H7A0.947700.582801.238700.0610*
H7B1.067500.590001.156000.0610*
H8A0.464400.252400.936000.0320*
H11A0.934100.110701.021500.0490*
H12A1.159800.122900.957100.0680*
H13A1.149300.203200.773000.0720*
H14A0.911400.268700.648200.0640*
H15A0.685400.259400.712700.0450*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0505 (6)0.0406 (5)0.0471 (6)0.0140 (4)0.0086 (5)0.0126 (4)
O20.0430 (5)0.0364 (5)0.0422 (6)0.0028 (4)0.0057 (4)0.0039 (4)
O30.0445 (6)0.0430 (6)0.0565 (7)0.0137 (4)0.0076 (5)0.0154 (5)
O40.0807 (8)0.0287 (5)0.0534 (7)0.0198 (5)0.0210 (6)0.0105 (4)
O50.0349 (5)0.0251 (4)0.0689 (7)0.0023 (3)0.0293 (5)0.0038 (4)
O60.0406 (5)0.0211 (4)0.0483 (6)0.0025 (3)0.0229 (4)0.0051 (4)
N10.0392 (6)0.0314 (5)0.0297 (6)0.0039 (4)0.0125 (4)0.0035 (4)
C10.0304 (5)0.0207 (5)0.0312 (6)0.0001 (4)0.0155 (5)0.0002 (4)
C20.0320 (6)0.0259 (5)0.0374 (7)0.0010 (4)0.0123 (5)0.0008 (5)
C30.0368 (6)0.0337 (6)0.0384 (7)0.0080 (5)0.0140 (5)0.0083 (5)
C40.0552 (8)0.0226 (5)0.0402 (7)0.0090 (5)0.0222 (6)0.0059 (5)
C50.0554 (8)0.0207 (5)0.0361 (7)0.0021 (5)0.0192 (6)0.0023 (5)
C60.0366 (6)0.0234 (5)0.0280 (6)0.0008 (4)0.0140 (5)0.0006 (4)
C70.0598 (9)0.0419 (8)0.0533 (10)0.0222 (7)0.0226 (8)0.0178 (7)
C80.0267 (5)0.0228 (5)0.0312 (6)0.0016 (4)0.0116 (4)0.0028 (4)
C90.0258 (5)0.0211 (5)0.0293 (6)0.0014 (4)0.0100 (4)0.0021 (4)
C100.0291 (5)0.0223 (5)0.0364 (6)0.0049 (4)0.0158 (5)0.0057 (4)
C110.0305 (6)0.0468 (8)0.0456 (8)0.0031 (5)0.0137 (6)0.0079 (6)
C120.0302 (7)0.0656 (10)0.0776 (12)0.0031 (6)0.0236 (7)0.0297 (9)
C130.0580 (10)0.0509 (9)0.0964 (14)0.0266 (8)0.0589 (10)0.0382 (9)
C140.0818 (12)0.0317 (7)0.0720 (11)0.0172 (7)0.0597 (10)0.0138 (7)
C150.0526 (8)0.0250 (6)0.0463 (8)0.0051 (5)0.0301 (7)0.0027 (5)
C160.0274 (5)0.0220 (5)0.0337 (6)0.0011 (4)0.0108 (4)0.0026 (4)
Geometric parameters (Å, º) top
O1—N11.2299 (16)C9—C101.4854 (18)
O2—N11.2307 (14)C9—C161.4902 (16)
O3—C31.3586 (19)C10—C151.3905 (19)
O3—C71.4384 (19)C10—C111.391 (2)
O4—C41.3706 (18)C11—C121.391 (2)
O4—C71.434 (2)C12—C131.377 (3)
O5—C161.2487 (17)C13—C141.374 (3)
O6—C161.2857 (14)C14—C151.393 (3)
O6—H60.8400C2—H20.9500
N1—C61.4532 (18)C5—H50.9500
C1—C21.4103 (19)C7—H7A0.9900
C1—C81.4779 (16)C7—H7B0.9900
C1—C61.3948 (16)C8—H8A0.9500
C2—C31.3683 (19)C11—H11A0.9500
C3—C41.386 (2)C12—H12A0.9500
C4—C51.359 (2)C13—H13A0.9500
C5—C61.4069 (17)C14—H14A0.9500
C8—C91.3404 (16)C15—H15A0.9500
O1···C7i3.143 (2)C14···C7iv3.352 (2)
O1···C3i3.1876 (19)C15···C23.585 (2)
O1···C4i3.1657 (19)C15···C13.204 (2)
O1···C16ii3.3569 (17)C16···O1iii3.3569 (17)
O1···O6ii3.0260 (15)C16···O3ii3.1754 (17)
O2···C9ii3.3326 (16)C16···O5vi3.3270 (15)
O2···C16ii3.3962 (16)C16···O2iii3.3962 (16)
O2···C82.6285 (16)C1···H15A2.9900
O3···O6iii2.9660 (16)C2···H7Biv2.9500
O3···O42.3136 (17)C3···H7Biv2.8300
O3···C16iii3.1754 (17)C4···H7Biv3.0900
O3···C4iv3.331 (2)C8···H15A2.8900
O4···O32.3136 (17)C9···H22.8700
O5···C12v3.383 (2)C10···H22.9200
O5···O6vi2.6067 (13)C12···H5x3.0500
O5···C16vi3.3270 (15)C13···H5x2.7500
O6···C7ii3.325 (2)C14···H5x3.0100
O6···C112.9461 (18)C14···H7Biv2.9400
O6···O1iii3.0260 (15)C14···H7Aiv3.0000
O6···O3ii2.9660 (16)C15···H7Biv3.0500
O6···O5vi2.6067 (13)C16···H11A2.9900
O1···H52.4000C16···H6vi2.6500
O1···H6ii2.9200H2···C92.8700
O1···H7Ai2.6000H2···C102.9200
O2···H2ii2.7800H2···O2iii2.7800
O2···H8A2.4300H5···O12.4000
O2···H11Aii2.7700H5···C12xi3.0500
O2···H13Av2.8400H5···C13xi2.7500
O5···H14Avii2.8200H5···C14xi3.0100
O5···H12Av2.5700H6···O5vi1.7700
O5···H7Aviii2.9100H6···C16vi2.6500
O5···H8A2.3500H6···H6vi2.3900
O5···H6vi1.7700H6···H12Axii2.5900
O6···H11A2.6100H6···O1iii2.9200
N1···C4i3.4003 (19)H7A···O5xiii2.9100
N1···H8A2.9100H7A···O1i2.6000
N1···H11Aii2.8900H7A···C14iv3.0000
C1···C153.204 (2)H7B···C2iv2.9500
C2···C103.2283 (17)H7B···C3iv2.8300
C2···C153.585 (2)H7B···C4iv3.0900
C3···O1i3.1875 (19)H7B···C14iv2.9400
C3···C7iv3.409 (2)H7B···C15iv3.0500
C4···O1i3.1657 (19)H8A···O22.4300
C4···N1i3.4003 (19)H8A···O52.3500
C4···O3iv3.331 (2)H8A···N12.9100
C5···C6i3.458 (2)H8A···H14Avii2.5200
C5···C5i3.408 (2)H11A···O62.6100
C6···C5i3.458 (2)H11A···C162.9900
C7···C3iv3.409 (2)H11A···O2iii2.7700
C7···C14iv3.352 (2)H11A···N1iii2.8900
C7···O6iii3.325 (2)H12A···O5ix2.5700
C7···O1i3.143 (2)H12A···H6xii2.5900
C8···O22.6285 (16)H13A···O2ix2.8400
C9···O2iii3.3326 (16)H14A···O5xiv2.8200
C10···C23.2283 (17)H14A···H8Axiv2.5200
C11···O62.9461 (18)H15A···C12.9900
C12···O5ix3.383 (2)H15A···C82.8900
C3—O3—C7105.51 (12)C11—C12—C13120.55 (17)
C4—O4—C7105.58 (11)C12—C13—C14119.90 (18)
C16—O6—H6109.00C13—C14—C15120.20 (16)
O1—N1—O2122.95 (12)C10—C15—C14120.30 (14)
O1—N1—C6117.91 (11)O5—C16—C9120.11 (10)
O2—N1—C6119.15 (11)O6—C16—C9116.59 (11)
C2—C1—C8116.15 (10)O5—C16—O6123.25 (11)
C6—C1—C8125.11 (12)C1—C2—H2121.00
C2—C1—C6118.20 (11)C3—C2—H2121.00
C1—C2—C3117.72 (12)C4—C5—H5122.00
O3—C3—C2127.21 (13)C6—C5—H5122.00
C2—C3—C4122.60 (14)O3—C7—H7A110.00
O3—C3—C4110.20 (12)O3—C7—H7B110.00
O4—C4—C3109.53 (13)O4—C7—H7A110.00
C3—C4—C5121.99 (12)O4—C7—H7B110.00
O4—C4—C5128.48 (12)H7A—C7—H7B109.00
C4—C5—C6115.73 (12)C1—C8—H8A117.00
N1—C6—C1119.71 (10)C9—C8—H8A117.00
C1—C6—C5123.73 (12)C10—C11—H11A120.00
N1—C6—C5116.53 (11)C12—C11—H11A120.00
O3—C7—O4107.33 (13)C11—C12—H12A120.00
C1—C8—C9125.27 (12)C13—C12—H12A120.00
C8—C9—C16116.24 (11)C12—C13—H13A120.00
C10—C9—C16120.50 (10)C14—C13—H13A120.00
C8—C9—C10123.25 (11)C13—C14—H14A120.00
C9—C10—C11122.48 (11)C15—C14—H14A120.00
C11—C10—C15119.06 (13)C10—C15—H15A120.00
C9—C10—C15118.44 (12)C14—C15—H15A120.00
C10—C11—C12119.92 (15)
C7—O3—C3—C2171.08 (15)O3—C3—C4—O41.18 (18)
C7—O3—C3—C49.19 (17)O4—C4—C5—C6177.81 (15)
C3—O3—C7—O413.58 (17)C3—C4—C5—C61.8 (2)
C7—O4—C4—C37.40 (18)C4—C5—C6—N1176.76 (13)
C7—O4—C4—C5172.23 (17)C4—C5—C6—C11.4 (2)
C4—O4—C7—O312.88 (17)C1—C8—C9—C16163.48 (11)
O1—N1—C6—C511.76 (18)C1—C8—C9—C1015.9 (2)
O1—N1—C6—C1166.50 (12)C8—C9—C10—C11126.92 (14)
O2—N1—C6—C113.24 (19)C10—C9—C16—O64.27 (17)
O2—N1—C6—C5168.50 (13)C16—C9—C10—C15128.95 (12)
C8—C1—C6—N17.1 (2)C8—C9—C10—C1551.72 (17)
C6—C1—C2—C31.40 (19)C16—C9—C10—C1152.42 (17)
C8—C1—C2—C3170.59 (12)C10—C9—C16—O5178.46 (12)
C2—C1—C6—N1178.29 (12)C8—C9—C16—O52.16 (18)
C2—C1—C6—C50.2 (2)C8—C9—C16—O6175.11 (12)
C8—C1—C6—C5171.04 (13)C9—C10—C11—C12176.01 (14)
C2—C1—C8—C954.48 (18)C11—C10—C15—C142.0 (2)
C6—C1—C8—C9134.16 (14)C15—C10—C11—C122.6 (2)
C1—C2—C3—C41.1 (2)C9—C10—C15—C14176.65 (12)
C1—C2—C3—O3179.21 (14)C10—C11—C12—C131.1 (3)
C2—C3—C4—O4179.07 (14)C11—C12—C13—C141.1 (3)
C2—C3—C4—C50.6 (2)C12—C13—C14—C151.6 (3)
O3—C3—C4—C5179.16 (14)C13—C14—C15—C100.1 (2)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+2, y+1, z+2; (v) x1, y, z; (vi) x+1, y, z+2; (vii) x1/2, y+1/2, z+1/2; (viii) x+3/2, y1/2, z+5/2; (ix) x+1, y, z; (x) x+3/2, y1/2, z+3/2; (xi) x+3/2, y+1/2, z+3/2; (xii) x+2, y, z+2; (xiii) x+3/2, y+1/2, z+5/2; (xiv) x+1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O5vi0.841.772.6067 (13)174
C7—H7A···O1i0.992.603.143 (2)115
C8—H8A···O50.952.352.7124 (15)102
C12—H12A···O5ix0.952.573.383 (2)144
Symmetry codes: (i) x+1, y+1, z+2; (vi) x+1, y, z+2; (ix) x+1, y, z.
 

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