In the solid-state structure of the title compound, C
16H
11NO
6, 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
CCDC reference: 627366
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.041
- wR factor = 0.112
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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.
Crystal data top
C16H11NO6 | F(000) = 648 |
Mr = 313.26 | Dx = 1.488 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 11122 reflections |
a = 8.8747 (6) Å | θ = 2.0–29.5° |
b = 15.4381 (13) Å | µ = 0.12 mm−1 |
c = 10.8315 (7) Å | T = 173 K |
β = 109.529 (5)° | Block, yellow |
V = 1398.64 (18) Å3 | 0.50 × 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 tube | Rint = 0.030 |
Graphite monochromator | θmax = 29.2°, θmin = 2.4° |
Detector resolution: 6.67 pixels mm-1 | h = −12→12 |
ω & φ scans | k = −21→21 |
11303 measured reflections | l = −14→14 |
3714 independent reflections | |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.31588 (13) | 0.47351 (7) | 0.73562 (11) | 0.0480 (3) | |
O2 | 0.35207 (12) | 0.33506 (6) | 0.73484 (10) | 0.0427 (3) | |
O3 | 0.97768 (13) | 0.47056 (7) | 1.15601 (12) | 0.0503 (4) | |
O4 | 0.83611 (16) | 0.58879 (7) | 1.04460 (12) | 0.0546 (4) | |
O5 | 0.45495 (11) | 0.10331 (6) | 0.97796 (11) | 0.0400 (3) | |
O6 | 0.65627 (11) | 0.03382 (5) | 0.94141 (10) | 0.0347 (3) | |
N1 | 0.39740 (13) | 0.40832 (7) | 0.77520 (11) | 0.0332 (3) | |
C1 | 0.63546 (14) | 0.34706 (7) | 0.94186 (12) | 0.0261 (3) | |
C2 | 0.78489 (15) | 0.36028 (8) | 1.04008 (13) | 0.0316 (3) | |
C3 | 0.83898 (16) | 0.44361 (9) | 1.06524 (14) | 0.0359 (4) | |
C4 | 0.75419 (18) | 0.51397 (8) | 0.99691 (14) | 0.0378 (4) | |
C5 | 0.61165 (18) | 0.50454 (8) | 0.89915 (14) | 0.0364 (4) | |
C6 | 0.55371 (15) | 0.41921 (7) | 0.87450 (12) | 0.0285 (3) | |
C7 | 0.9668 (2) | 0.56348 (10) | 1.15806 (17) | 0.0507 (5) | |
C8 | 0.56910 (14) | 0.25852 (7) | 0.93176 (12) | 0.0264 (3) | |
C9 | 0.64469 (13) | 0.18610 (7) | 0.91706 (12) | 0.0252 (3) | |
C10 | 0.78835 (14) | 0.18626 (7) | 0.87578 (12) | 0.0281 (3) | |
C11 | 0.92924 (16) | 0.14410 (10) | 0.94660 (15) | 0.0407 (4) | |
C12 | 1.06315 (18) | 0.15095 (12) | 0.9077 (2) | 0.0564 (6) | |
C13 | 1.0568 (2) | 0.19803 (11) | 0.7981 (2) | 0.0601 (6) | |
C14 | 0.9166 (2) | 0.23751 (9) | 0.72511 (19) | 0.0533 (6) | |
C15 | 0.78200 (18) | 0.23191 (8) | 0.76348 (15) | 0.0379 (4) | |
C16 | 0.57775 (14) | 0.10303 (7) | 0.94604 (12) | 0.0276 (3) | |
H2 | 0.84590 | 0.31290 | 1.08720 | 0.0380* | |
H5 | 0.55480 | 0.55250 | 0.85060 | 0.0440* | |
H6 | 0.61470 | −0.00860 | 0.96650 | 0.0520* | |
H7A | 0.94770 | 0.58280 | 1.23870 | 0.0610* | |
H7B | 1.06750 | 0.59000 | 1.15600 | 0.0610* | |
H8A | 0.46440 | 0.25240 | 0.93600 | 0.0320* | |
H11A | 0.93410 | 0.11070 | 1.02150 | 0.0490* | |
H12A | 1.15980 | 0.12290 | 0.95710 | 0.0680* | |
H13A | 1.14930 | 0.20320 | 0.77300 | 0.0720* | |
H14A | 0.91140 | 0.26870 | 0.64820 | 0.0640* | |
H15A | 0.68540 | 0.25940 | 0.71270 | 0.0450* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0505 (6) | 0.0406 (5) | 0.0471 (6) | 0.0140 (4) | 0.0086 (5) | 0.0126 (4) |
O2 | 0.0430 (5) | 0.0364 (5) | 0.0422 (6) | −0.0028 (4) | 0.0057 (4) | −0.0039 (4) |
O3 | 0.0445 (6) | 0.0430 (6) | 0.0565 (7) | −0.0137 (4) | 0.0076 (5) | −0.0154 (5) |
O4 | 0.0807 (8) | 0.0287 (5) | 0.0534 (7) | −0.0198 (5) | 0.0210 (6) | −0.0105 (4) |
O5 | 0.0349 (5) | 0.0251 (4) | 0.0689 (7) | −0.0023 (3) | 0.0293 (5) | 0.0038 (4) |
O6 | 0.0406 (5) | 0.0211 (4) | 0.0483 (6) | 0.0025 (3) | 0.0229 (4) | 0.0051 (4) |
N1 | 0.0392 (6) | 0.0314 (5) | 0.0297 (6) | 0.0039 (4) | 0.0125 (4) | 0.0035 (4) |
C1 | 0.0304 (5) | 0.0207 (5) | 0.0312 (6) | −0.0001 (4) | 0.0155 (5) | 0.0002 (4) |
C2 | 0.0320 (6) | 0.0259 (5) | 0.0374 (7) | −0.0010 (4) | 0.0123 (5) | −0.0008 (5) |
C3 | 0.0368 (6) | 0.0337 (6) | 0.0384 (7) | −0.0080 (5) | 0.0140 (5) | −0.0083 (5) |
C4 | 0.0552 (8) | 0.0226 (5) | 0.0402 (7) | −0.0090 (5) | 0.0222 (6) | −0.0059 (5) |
C5 | 0.0554 (8) | 0.0207 (5) | 0.0361 (7) | 0.0021 (5) | 0.0192 (6) | 0.0023 (5) |
C6 | 0.0366 (6) | 0.0234 (5) | 0.0280 (6) | 0.0008 (4) | 0.0140 (5) | 0.0006 (4) |
C7 | 0.0598 (9) | 0.0419 (8) | 0.0533 (10) | −0.0222 (7) | 0.0226 (8) | −0.0178 (7) |
C8 | 0.0267 (5) | 0.0228 (5) | 0.0312 (6) | −0.0016 (4) | 0.0116 (4) | 0.0028 (4) |
C9 | 0.0258 (5) | 0.0211 (5) | 0.0293 (6) | −0.0014 (4) | 0.0100 (4) | 0.0021 (4) |
C10 | 0.0291 (5) | 0.0223 (5) | 0.0364 (6) | −0.0049 (4) | 0.0158 (5) | −0.0057 (4) |
C11 | 0.0305 (6) | 0.0468 (8) | 0.0456 (8) | 0.0031 (5) | 0.0137 (6) | −0.0079 (6) |
C12 | 0.0302 (7) | 0.0656 (10) | 0.0776 (12) | −0.0031 (6) | 0.0236 (7) | −0.0297 (9) |
C13 | 0.0580 (10) | 0.0509 (9) | 0.0964 (14) | −0.0266 (8) | 0.0589 (10) | −0.0382 (9) |
C14 | 0.0818 (12) | 0.0317 (7) | 0.0720 (11) | −0.0172 (7) | 0.0597 (10) | −0.0138 (7) |
C15 | 0.0526 (8) | 0.0250 (6) | 0.0463 (8) | −0.0051 (5) | 0.0301 (7) | −0.0027 (5) |
C16 | 0.0274 (5) | 0.0220 (5) | 0.0337 (6) | −0.0011 (4) | 0.0108 (4) | 0.0026 (4) |
Geometric parameters (Å, º) top
O1—N1 | 1.2299 (16) | C9—C10 | 1.4854 (18) |
O2—N1 | 1.2307 (14) | C9—C16 | 1.4902 (16) |
O3—C3 | 1.3586 (19) | C10—C15 | 1.3905 (19) |
O3—C7 | 1.4384 (19) | C10—C11 | 1.391 (2) |
O4—C4 | 1.3706 (18) | C11—C12 | 1.391 (2) |
O4—C7 | 1.434 (2) | C12—C13 | 1.377 (3) |
O5—C16 | 1.2487 (17) | C13—C14 | 1.374 (3) |
O6—C16 | 1.2857 (14) | C14—C15 | 1.393 (3) |
O6—H6 | 0.8400 | C2—H2 | 0.9500 |
N1—C6 | 1.4532 (18) | C5—H5 | 0.9500 |
C1—C2 | 1.4103 (19) | C7—H7A | 0.9900 |
C1—C8 | 1.4779 (16) | C7—H7B | 0.9900 |
C1—C6 | 1.3948 (16) | C8—H8A | 0.9500 |
C2—C3 | 1.3683 (19) | C11—H11A | 0.9500 |
C3—C4 | 1.386 (2) | C12—H12A | 0.9500 |
C4—C5 | 1.359 (2) | C13—H13A | 0.9500 |
C5—C6 | 1.4069 (17) | C14—H14A | 0.9500 |
C8—C9 | 1.3404 (16) | C15—H15A | 0.9500 |
| | | |
O1···C7i | 3.143 (2) | C14···C7iv | 3.352 (2) |
O1···C3i | 3.1876 (19) | C15···C2 | 3.585 (2) |
O1···C4i | 3.1657 (19) | C15···C1 | 3.204 (2) |
O1···C16ii | 3.3569 (17) | C16···O1iii | 3.3569 (17) |
O1···O6ii | 3.0260 (15) | C16···O3ii | 3.1754 (17) |
O2···C9ii | 3.3326 (16) | C16···O5vi | 3.3270 (15) |
O2···C16ii | 3.3962 (16) | C16···O2iii | 3.3962 (16) |
O2···C8 | 2.6285 (16) | C1···H15A | 2.9900 |
O3···O6iii | 2.9660 (16) | C2···H7Biv | 2.9500 |
O3···O4 | 2.3136 (17) | C3···H7Biv | 2.8300 |
O3···C16iii | 3.1754 (17) | C4···H7Biv | 3.0900 |
O3···C4iv | 3.331 (2) | C8···H15A | 2.8900 |
O4···O3 | 2.3136 (17) | C9···H2 | 2.8700 |
O5···C12v | 3.383 (2) | C10···H2 | 2.9200 |
O5···O6vi | 2.6067 (13) | C12···H5x | 3.0500 |
O5···C16vi | 3.3270 (15) | C13···H5x | 2.7500 |
O6···C7ii | 3.325 (2) | C14···H5x | 3.0100 |
O6···C11 | 2.9461 (18) | C14···H7Biv | 2.9400 |
O6···O1iii | 3.0260 (15) | C14···H7Aiv | 3.0000 |
O6···O3ii | 2.9660 (16) | C15···H7Biv | 3.0500 |
O6···O5vi | 2.6067 (13) | C16···H11A | 2.9900 |
O1···H5 | 2.4000 | C16···H6vi | 2.6500 |
O1···H6ii | 2.9200 | H2···C9 | 2.8700 |
O1···H7Ai | 2.6000 | H2···C10 | 2.9200 |
O2···H2ii | 2.7800 | H2···O2iii | 2.7800 |
O2···H8A | 2.4300 | H5···O1 | 2.4000 |
O2···H11Aii | 2.7700 | H5···C12xi | 3.0500 |
O2···H13Av | 2.8400 | H5···C13xi | 2.7500 |
O5···H14Avii | 2.8200 | H5···C14xi | 3.0100 |
O5···H12Av | 2.5700 | H6···O5vi | 1.7700 |
O5···H7Aviii | 2.9100 | H6···C16vi | 2.6500 |
O5···H8A | 2.3500 | H6···H6vi | 2.3900 |
O5···H6vi | 1.7700 | H6···H12Axii | 2.5900 |
O6···H11A | 2.6100 | H6···O1iii | 2.9200 |
N1···C4i | 3.4003 (19) | H7A···O5xiii | 2.9100 |
N1···H8A | 2.9100 | H7A···O1i | 2.6000 |
N1···H11Aii | 2.8900 | H7A···C14iv | 3.0000 |
C1···C15 | 3.204 (2) | H7B···C2iv | 2.9500 |
C2···C10 | 3.2283 (17) | H7B···C3iv | 2.8300 |
C2···C15 | 3.585 (2) | H7B···C4iv | 3.0900 |
C3···O1i | 3.1875 (19) | H7B···C14iv | 2.9400 |
C3···C7iv | 3.409 (2) | H7B···C15iv | 3.0500 |
C4···O1i | 3.1657 (19) | H8A···O2 | 2.4300 |
C4···N1i | 3.4003 (19) | H8A···O5 | 2.3500 |
C4···O3iv | 3.331 (2) | H8A···N1 | 2.9100 |
C5···C6i | 3.458 (2) | H8A···H14Avii | 2.5200 |
C5···C5i | 3.408 (2) | H11A···O6 | 2.6100 |
C6···C5i | 3.458 (2) | H11A···C16 | 2.9900 |
C7···C3iv | 3.409 (2) | H11A···O2iii | 2.7700 |
C7···C14iv | 3.352 (2) | H11A···N1iii | 2.8900 |
C7···O6iii | 3.325 (2) | H12A···O5ix | 2.5700 |
C7···O1i | 3.143 (2) | H12A···H6xii | 2.5900 |
C8···O2 | 2.6285 (16) | H13A···O2ix | 2.8400 |
C9···O2iii | 3.3326 (16) | H14A···O5xiv | 2.8200 |
C10···C2 | 3.2283 (17) | H14A···H8Axiv | 2.5200 |
C11···O6 | 2.9461 (18) | H15A···C1 | 2.9900 |
C12···O5ix | 3.383 (2) | H15A···C8 | 2.8900 |
| | | |
C3—O3—C7 | 105.51 (12) | C11—C12—C13 | 120.55 (17) |
C4—O4—C7 | 105.58 (11) | C12—C13—C14 | 119.90 (18) |
C16—O6—H6 | 109.00 | C13—C14—C15 | 120.20 (16) |
O1—N1—O2 | 122.95 (12) | C10—C15—C14 | 120.30 (14) |
O1—N1—C6 | 117.91 (11) | O5—C16—C9 | 120.11 (10) |
O2—N1—C6 | 119.15 (11) | O6—C16—C9 | 116.59 (11) |
C2—C1—C8 | 116.15 (10) | O5—C16—O6 | 123.25 (11) |
C6—C1—C8 | 125.11 (12) | C1—C2—H2 | 121.00 |
C2—C1—C6 | 118.20 (11) | C3—C2—H2 | 121.00 |
C1—C2—C3 | 117.72 (12) | C4—C5—H5 | 122.00 |
O3—C3—C2 | 127.21 (13) | C6—C5—H5 | 122.00 |
C2—C3—C4 | 122.60 (14) | O3—C7—H7A | 110.00 |
O3—C3—C4 | 110.20 (12) | O3—C7—H7B | 110.00 |
O4—C4—C3 | 109.53 (13) | O4—C7—H7A | 110.00 |
C3—C4—C5 | 121.99 (12) | O4—C7—H7B | 110.00 |
O4—C4—C5 | 128.48 (12) | H7A—C7—H7B | 109.00 |
C4—C5—C6 | 115.73 (12) | C1—C8—H8A | 117.00 |
N1—C6—C1 | 119.71 (10) | C9—C8—H8A | 117.00 |
C1—C6—C5 | 123.73 (12) | C10—C11—H11A | 120.00 |
N1—C6—C5 | 116.53 (11) | C12—C11—H11A | 120.00 |
O3—C7—O4 | 107.33 (13) | C11—C12—H12A | 120.00 |
C1—C8—C9 | 125.27 (12) | C13—C12—H12A | 120.00 |
C8—C9—C16 | 116.24 (11) | C12—C13—H13A | 120.00 |
C10—C9—C16 | 120.50 (10) | C14—C13—H13A | 120.00 |
C8—C9—C10 | 123.25 (11) | C13—C14—H14A | 120.00 |
C9—C10—C11 | 122.48 (11) | C15—C14—H14A | 120.00 |
C11—C10—C15 | 119.06 (13) | C10—C15—H15A | 120.00 |
C9—C10—C15 | 118.44 (12) | C14—C15—H15A | 120.00 |
C10—C11—C12 | 119.92 (15) | | |
| | | |
C7—O3—C3—C2 | −171.08 (15) | O3—C3—C4—O4 | −1.18 (18) |
C7—O3—C3—C4 | 9.19 (17) | O4—C4—C5—C6 | −177.81 (15) |
C3—O3—C7—O4 | −13.58 (17) | C3—C4—C5—C6 | 1.8 (2) |
C7—O4—C4—C3 | −7.40 (18) | C4—C5—C6—N1 | 176.76 (13) |
C7—O4—C4—C5 | 172.23 (17) | C4—C5—C6—C1 | −1.4 (2) |
C4—O4—C7—O3 | 12.88 (17) | C1—C8—C9—C16 | 163.48 (11) |
O1—N1—C6—C5 | −11.76 (18) | C1—C8—C9—C10 | −15.9 (2) |
O1—N1—C6—C1 | 166.50 (12) | C8—C9—C10—C11 | 126.92 (14) |
O2—N1—C6—C1 | −13.24 (19) | C10—C9—C16—O6 | 4.27 (17) |
O2—N1—C6—C5 | 168.50 (13) | C16—C9—C10—C15 | 128.95 (12) |
C8—C1—C6—N1 | −7.1 (2) | C8—C9—C10—C15 | −51.72 (17) |
C6—C1—C2—C3 | 1.40 (19) | C16—C9—C10—C11 | −52.42 (17) |
C8—C1—C2—C3 | −170.59 (12) | C10—C9—C16—O5 | −178.46 (12) |
C2—C1—C6—N1 | −178.29 (12) | C8—C9—C16—O5 | 2.16 (18) |
C2—C1—C6—C5 | −0.2 (2) | C8—C9—C16—O6 | −175.11 (12) |
C8—C1—C6—C5 | 171.04 (13) | C9—C10—C11—C12 | −176.01 (14) |
C2—C1—C8—C9 | −54.48 (18) | C11—C10—C15—C14 | −2.0 (2) |
C6—C1—C8—C9 | 134.16 (14) | C15—C10—C11—C12 | 2.6 (2) |
C1—C2—C3—C4 | −1.1 (2) | C9—C10—C15—C14 | 176.65 (12) |
C1—C2—C3—O3 | 179.21 (14) | C10—C11—C12—C13 | −1.1 (3) |
C2—C3—C4—O4 | 179.07 (14) | C11—C12—C13—C14 | −1.1 (3) |
C2—C3—C4—C5 | −0.6 (2) | C12—C13—C14—C15 | 1.6 (3) |
O3—C3—C4—C5 | 179.16 (14) | C13—C14—C15—C10 | −0.1 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z+2; (v) x−1, y, z; (vi) −x+1, −y, −z+2; (vii) x−1/2, −y+1/2, z+1/2; (viii) −x+3/2, y−1/2, −z+5/2; (ix) x+1, y, z; (x) −x+3/2, y−1/2, −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, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O5vi | 0.84 | 1.77 | 2.6067 (13) | 174 |
C7—H7A···O1i | 0.99 | 2.60 | 3.143 (2) | 115 |
C8—H8A···O5 | 0.95 | 2.35 | 2.7124 (15) | 102 |
C12—H12A···O5ix | 0.95 | 2.57 | 3.383 (2) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (vi) −x+1, −y, −z+2; (ix) x+1, y, z. |