The benzophenone derivative, methyl [2-(3-nitrobenzoyl)benzoylamino]acetate, (3), exists in equilibrium with the title compound, C
17H
14N
2O
6, (4), a tricyclic tertiary alcohol, with the position of the equilibrium lying strongly in favour of (4). The crystal structure consists of discrete molecules of (4) stabilized by O—H
O and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 227894
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.109
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N2 = 5.05 su
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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
R)-[1-Hydroxy-1-(3-nitrophenyl)-3-oxo-1,3-dihydroisoindol-2-yl] acetic
acid methyl ester
top
Crystal data top
C17H14N2O6 | F(000) = 712 |
Mr = 342.30 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Melting point: 430–432 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0330 (3) Å | Cell parameters from 18179 reflections |
b = 6.8414 (1) Å | θ = 2.9–28.3° |
c = 16.1593 (4) Å | µ = 0.11 mm−1 |
β = 111.0117 (8)° | T = 123 K |
V = 1551.42 (5) Å3 | Prismatic, colourless |
Z = 4 | 0.15 × 0.15 × 0.15 mm |
Data collection top
Nonius KappaCCD diffractometer | 2085 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.078 |
Horizonally mounted graphite crystal monochromator | θmax = 28.3°, θmin = 2.9° |
Detector resolution: 9 pixels mm-1 | h = −19→19 |
CCD rotation images, thick slices scans | k = −9→9 |
18179 measured reflections | l = −21→21 |
3764 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0474P)2 + 0.1011P] where P = (Fo2 + 2Fc2)/3 |
3764 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.18303 (12) | 0.8627 (3) | 0.02666 (11) | 0.0224 (4) | |
C2 | 0.09616 (11) | 1.1402 (3) | 0.04578 (12) | 0.0235 (4) | |
C3 | 0.09861 (11) | 1.1477 (3) | −0.04483 (11) | 0.0219 (4) | |
C4 | 0.15044 (11) | 0.9885 (3) | −0.05634 (11) | 0.0210 (4) | |
C5 | 0.16389 (12) | 0.9572 (3) | −0.13559 (11) | 0.0240 (4) | |
H5 | 0.2007 | 0.8501 | −0.1429 | 0.029* | |
C6 | 0.12158 (11) | 1.0883 (3) | −0.20416 (12) | 0.0257 (4) | |
H6 | 0.1294 | 1.0704 | −0.2595 | 0.031* | |
C7 | 0.06821 (12) | 1.2449 (3) | −0.19329 (12) | 0.0269 (5) | |
H7 | 0.0391 | 1.3308 | −0.2417 | 0.032* | |
C8 | 0.05652 (11) | 1.2788 (3) | −0.11312 (12) | 0.0248 (4) | |
H8 | 0.0210 | 1.3876 | −0.1053 | 0.030* | |
C9 | 0.28998 (11) | 0.8325 (3) | 0.06921 (11) | 0.0220 (4) | |
C10 | 0.35196 (12) | 0.9790 (3) | 0.06557 (11) | 0.0240 (4) | |
H10 | 0.3283 | 1.0971 | 0.0346 | 0.029* | |
C11 | 0.44885 (12) | 0.9506 (3) | 0.10780 (11) | 0.0268 (5) | |
C12 | 0.48671 (13) | 0.7822 (3) | 0.15411 (12) | 0.0316 (5) | |
H12 | 0.5536 | 0.7668 | 0.1828 | 0.038* | |
C13 | 0.42459 (13) | 0.6375 (3) | 0.15734 (12) | 0.0339 (5) | |
H13 | 0.4488 | 0.5201 | 0.1887 | 0.041* | |
C14 | 0.32682 (12) | 0.6608 (3) | 0.11529 (11) | 0.0291 (5) | |
H14 | 0.2849 | 0.5592 | 0.1179 | 0.035* | |
C15 | 0.16232 (12) | 0.9229 (3) | 0.17498 (11) | 0.0269 (5) | |
H15A | 0.1766 | 0.7812 | 0.1813 | 0.032* | |
H15B | 0.1027 | 0.9447 | 0.1866 | 0.032* | |
C16 | 0.24285 (12) | 1.0332 (3) | 0.24370 (11) | 0.0230 (4) | |
C17 | 0.31871 (13) | 1.0694 (3) | 0.39964 (11) | 0.0339 (5) | |
H17A | 0.3821 | 1.0169 | 0.4085 | 0.051* | |
H17B | 0.3032 | 1.0451 | 0.4527 | 0.051* | |
H17C | 0.3181 | 1.2104 | 0.3888 | 0.051* | |
N1 | 0.14762 (9) | 0.9811 (2) | 0.08559 (9) | 0.0228 (4) | |
N2 | 0.51414 (11) | 1.1062 (3) | 0.10171 (11) | 0.0350 (4) | |
O1 | 0.14058 (8) | 0.67651 (18) | 0.01312 (8) | 0.0290 (3) | |
H1 | 0.0813 | 0.6881 | −0.0117 | 0.044* | |
O2 | 0.05434 (8) | 1.25021 (19) | 0.08026 (8) | 0.0295 (3) | |
O3 | 0.24871 (8) | 0.97435 (19) | 0.32402 (8) | 0.0278 (3) | |
O4 | 0.29204 (8) | 1.1552 (2) | 0.22824 (8) | 0.0320 (3) | |
O5 | 0.48025 (10) | 1.2530 (2) | 0.05824 (10) | 0.0522 (5) | |
O6 | 0.59985 (9) | 1.0820 (2) | 0.13972 (10) | 0.0562 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0254 (9) | 0.0209 (11) | 0.0207 (9) | −0.0019 (8) | 0.0080 (8) | −0.0041 (8) |
C2 | 0.0152 (9) | 0.0264 (11) | 0.0265 (10) | −0.0052 (8) | 0.0047 (8) | −0.0077 (9) |
C3 | 0.0161 (9) | 0.0231 (11) | 0.0245 (10) | −0.0046 (8) | 0.0048 (7) | −0.0044 (8) |
C4 | 0.0175 (9) | 0.0243 (11) | 0.0188 (10) | −0.0025 (8) | 0.0036 (7) | −0.0034 (8) |
C5 | 0.0225 (9) | 0.0267 (11) | 0.0218 (10) | 0.0005 (8) | 0.0066 (8) | −0.0029 (8) |
C6 | 0.0239 (9) | 0.0320 (12) | 0.0213 (10) | −0.0057 (9) | 0.0081 (8) | −0.0011 (9) |
C7 | 0.0215 (9) | 0.0273 (12) | 0.0281 (11) | −0.0047 (8) | 0.0041 (8) | 0.0062 (9) |
C8 | 0.0180 (9) | 0.0197 (10) | 0.0341 (11) | −0.0030 (8) | 0.0061 (8) | −0.0012 (9) |
C9 | 0.0247 (9) | 0.0247 (11) | 0.0158 (9) | 0.0038 (8) | 0.0064 (8) | −0.0007 (8) |
C10 | 0.0234 (9) | 0.0274 (11) | 0.0209 (9) | 0.0052 (8) | 0.0076 (8) | 0.0015 (8) |
C11 | 0.0229 (10) | 0.0364 (12) | 0.0214 (10) | 0.0004 (9) | 0.0081 (8) | −0.0020 (9) |
C12 | 0.0252 (10) | 0.0441 (14) | 0.0235 (10) | 0.0113 (10) | 0.0062 (8) | −0.0018 (10) |
C13 | 0.0385 (12) | 0.0337 (13) | 0.0253 (10) | 0.0122 (10) | 0.0063 (9) | 0.0062 (9) |
C14 | 0.0322 (11) | 0.0319 (12) | 0.0219 (10) | 0.0014 (9) | 0.0084 (8) | 0.0001 (9) |
C15 | 0.0251 (10) | 0.0329 (12) | 0.0234 (10) | −0.0058 (9) | 0.0097 (8) | −0.0032 (9) |
C16 | 0.0202 (9) | 0.0280 (11) | 0.0224 (10) | 0.0024 (8) | 0.0095 (8) | 0.0001 (8) |
C17 | 0.0312 (10) | 0.0437 (14) | 0.0203 (10) | −0.0043 (10) | 0.0015 (9) | −0.0036 (9) |
N1 | 0.0216 (8) | 0.0279 (10) | 0.0189 (8) | 0.0001 (7) | 0.0073 (6) | −0.0027 (7) |
N2 | 0.0238 (10) | 0.0501 (12) | 0.0303 (9) | −0.0015 (8) | 0.0087 (8) | −0.0019 (9) |
O1 | 0.0281 (7) | 0.0252 (8) | 0.0304 (7) | −0.0050 (6) | 0.0064 (6) | −0.0021 (6) |
O2 | 0.0233 (7) | 0.0332 (8) | 0.0330 (7) | −0.0019 (6) | 0.0115 (6) | −0.0099 (6) |
O3 | 0.0286 (7) | 0.0329 (8) | 0.0195 (7) | −0.0043 (6) | 0.0055 (5) | 0.0004 (6) |
O4 | 0.0277 (7) | 0.0409 (9) | 0.0269 (7) | −0.0127 (6) | 0.0089 (6) | −0.0013 (6) |
O5 | 0.0323 (8) | 0.0504 (11) | 0.0627 (11) | −0.0065 (8) | 0.0035 (8) | 0.0185 (9) |
O6 | 0.0172 (8) | 0.0766 (13) | 0.0680 (11) | −0.0003 (7) | 0.0069 (7) | 0.0113 (9) |
Geometric parameters (Å, º) top
C1—O1 | 1.406 (2) | C11—C12 | 1.380 (3) |
C1—N1 | 1.487 (2) | C11—N2 | 1.475 (2) |
C1—C9 | 1.519 (2) | C12—C13 | 1.375 (3) |
C1—C4 | 1.519 (2) | C12—H12 | 0.95 |
C2—O2 | 1.234 (2) | C13—C14 | 1.390 (3) |
C2—N1 | 1.357 (2) | C13—H13 | 0.95 |
C2—C3 | 1.479 (2) | C14—H14 | 0.95 |
C3—C8 | 1.386 (2) | C15—N1 | 1.437 (2) |
C3—C4 | 1.390 (2) | C15—C16 | 1.518 (2) |
C4—C5 | 1.383 (2) | C15—H15A | 0.99 |
C5—C6 | 1.390 (2) | C15—H15B | 0.99 |
C5—H5 | 0.95 | C16—O4 | 1.199 (2) |
C6—C7 | 1.387 (2) | C16—O3 | 1.331 (2) |
C6—H6 | 0.95 | C17—O3 | 1.450 (2) |
C7—C8 | 1.388 (2) | C17—H17A | 0.98 |
C7—H7 | 0.95 | C17—H17B | 0.98 |
C8—H8 | 0.95 | C17—H17C | 0.98 |
C9—C10 | 1.384 (2) | N2—O6 | 1.2237 (19) |
C9—C14 | 1.395 (2) | N2—O5 | 1.227 (2) |
C10—C11 | 1.383 (2) | O1—H1 | 0.84 |
C10—H10 | 0.95 | | |
| | | |
O1—C1—N1 | 110.27 (14) | C12—C11—N2 | 118.93 (16) |
O1—C1—C9 | 107.16 (14) | C10—C11—N2 | 118.28 (17) |
N1—C1—C9 | 110.38 (13) | C13—C12—C11 | 117.89 (17) |
O1—C1—C4 | 113.02 (13) | C13—C12—H12 | 121.1 |
N1—C1—C4 | 100.40 (14) | C11—C12—H12 | 121.1 |
C9—C1—C4 | 115.50 (14) | C12—C13—C14 | 120.86 (19) |
O2—C2—N1 | 124.84 (17) | C12—C13—H13 | 119.6 |
O2—C2—C3 | 128.57 (17) | C14—C13—H13 | 119.6 |
N1—C2—C3 | 106.56 (15) | C13—C14—C9 | 120.35 (19) |
C8—C3—C4 | 121.21 (16) | C13—C14—H14 | 119.8 |
C8—C3—C2 | 130.13 (17) | C9—C14—H14 | 119.8 |
C4—C3—C2 | 108.63 (16) | N1—C15—C16 | 113.09 (15) |
C5—C4—C3 | 121.35 (16) | N1—C15—H15A | 109.0 |
C5—C4—C1 | 128.45 (16) | C16—C15—H15A | 109.0 |
C3—C4—C1 | 110.16 (15) | N1—C15—H15B | 109.0 |
C4—C5—C6 | 117.47 (17) | C16—C15—H15B | 109.0 |
C4—C5—H5 | 121.3 | H15A—C15—H15B | 107.8 |
C6—C5—H5 | 121.3 | O4—C16—O3 | 125.69 (16) |
C7—C6—C5 | 121.18 (17) | O4—C16—C15 | 125.69 (16) |
C7—C6—H6 | 119.4 | O3—C16—C15 | 108.61 (15) |
C5—C6—H6 | 119.4 | O3—C17—H17A | 109.5 |
C6—C7—C8 | 121.32 (17) | O3—C17—H17B | 109.5 |
C6—C7—H7 | 119.3 | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 119.3 | O3—C17—H17C | 109.5 |
C3—C8—C7 | 117.44 (17) | H17A—C17—H17C | 109.5 |
C3—C8—H8 | 121.3 | H17B—C17—H17C | 109.5 |
C7—C8—H8 | 121.3 | C2—N1—C15 | 123.72 (15) |
C10—C9—C14 | 119.21 (16) | C2—N1—C1 | 114.07 (14) |
C10—C9—C1 | 120.13 (16) | C15—N1—C1 | 122.10 (14) |
C14—C9—C1 | 120.61 (16) | O6—N2—O5 | 123.01 (17) |
C11—C10—C9 | 118.90 (17) | O6—N2—C11 | 118.34 (17) |
C11—C10—H10 | 120.6 | O5—N2—C11 | 118.65 (15) |
C9—C10—H10 | 120.6 | C1—O1—H1 | 109.5 |
C12—C11—C10 | 122.79 (18) | C16—O3—C17 | 117.41 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.99 | 2.819 (2) | 171 |
C5—H5···O3ii | 0.95 | 2.45 | 3.371 (2) | 163 |
C12—H12···O4iii | 0.95 | 2.38 | 3.301 (2) | 165 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2. |