Download citation
Download citation
link to html
The benzo­phenone derivative, methyl [2-(3-nitro­benzoyl)­benzoyl­amino]­acetate, (3), exists in equilibrium with the title compound, C17H14N2O6, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025790/ci6299sup1.cif
Contains datablocks k20_03, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025790/ci62994sup2.hkl
Contains datablock 4

CCDC reference: 227894

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](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

Computing details top

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
C17H14N2O6F(000) = 712
Mr = 342.30Dx = 1.466 Mg m3
Monoclinic, P21/cMelting point: 430–432 K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.0330 (3) ÅCell parameters from 18179 reflections
b = 6.8414 (1) Åθ = 2.9–28.3°
c = 16.1593 (4) ŵ = 0.11 mm1
β = 111.0117 (8)°T = 123 K
V = 1551.42 (5) Å3Prismatic, colourless
Z = 40.15 × 0.15 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer
2085 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Horizonally mounted graphite crystal monochromatorθmax = 28.3°, θmin = 2.9°
Detector resolution: 9 pixels mm-1h = 1919
CCD rotation images, thick slices scansk = 99
18179 measured reflectionsl = 2121
3764 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.28 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*/Ueq
C10.18303 (12)0.8627 (3)0.02666 (11)0.0224 (4)
C20.09616 (11)1.1402 (3)0.04578 (12)0.0235 (4)
C30.09861 (11)1.1477 (3)0.04483 (11)0.0219 (4)
C40.15044 (11)0.9885 (3)0.05634 (11)0.0210 (4)
C50.16389 (12)0.9572 (3)0.13559 (11)0.0240 (4)
H50.20070.85010.14290.029*
C60.12158 (11)1.0883 (3)0.20416 (12)0.0257 (4)
H60.12941.07040.25950.031*
C70.06821 (12)1.2449 (3)0.19329 (12)0.0269 (5)
H70.03911.33080.24170.032*
C80.05652 (11)1.2788 (3)0.11312 (12)0.0248 (4)
H80.02101.38760.10530.030*
C90.28998 (11)0.8325 (3)0.06921 (11)0.0220 (4)
C100.35196 (12)0.9790 (3)0.06557 (11)0.0240 (4)
H100.32831.09710.03460.029*
C110.44885 (12)0.9506 (3)0.10780 (11)0.0268 (5)
C120.48671 (13)0.7822 (3)0.15411 (12)0.0316 (5)
H120.55360.76680.18280.038*
C130.42459 (13)0.6375 (3)0.15734 (12)0.0339 (5)
H130.44880.52010.18870.041*
C140.32682 (12)0.6608 (3)0.11529 (11)0.0291 (5)
H140.28490.55920.11790.035*
C150.16232 (12)0.9229 (3)0.17498 (11)0.0269 (5)
H15A0.17660.78120.18130.032*
H15B0.10270.94470.18660.032*
C160.24285 (12)1.0332 (3)0.24370 (11)0.0230 (4)
C170.31871 (13)1.0694 (3)0.39964 (11)0.0339 (5)
H17A0.38211.01690.40850.051*
H17B0.30321.04510.45270.051*
H17C0.31811.21040.38880.051*
N10.14762 (9)0.9811 (2)0.08559 (9)0.0228 (4)
N20.51414 (11)1.1062 (3)0.10171 (11)0.0350 (4)
O10.14058 (8)0.67651 (18)0.01312 (8)0.0290 (3)
H10.08130.68810.01170.044*
O20.05434 (8)1.25021 (19)0.08026 (8)0.0295 (3)
O30.24871 (8)0.97435 (19)0.32402 (8)0.0278 (3)
O40.29204 (8)1.1552 (2)0.22824 (8)0.0320 (3)
O50.48025 (10)1.2530 (2)0.05824 (10)0.0522 (5)
O60.59985 (9)1.0820 (2)0.13972 (10)0.0562 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0254 (9)0.0209 (11)0.0207 (9)0.0019 (8)0.0080 (8)0.0041 (8)
C20.0152 (9)0.0264 (11)0.0265 (10)0.0052 (8)0.0047 (8)0.0077 (9)
C30.0161 (9)0.0231 (11)0.0245 (10)0.0046 (8)0.0048 (7)0.0044 (8)
C40.0175 (9)0.0243 (11)0.0188 (10)0.0025 (8)0.0036 (7)0.0034 (8)
C50.0225 (9)0.0267 (11)0.0218 (10)0.0005 (8)0.0066 (8)0.0029 (8)
C60.0239 (9)0.0320 (12)0.0213 (10)0.0057 (9)0.0081 (8)0.0011 (9)
C70.0215 (9)0.0273 (12)0.0281 (11)0.0047 (8)0.0041 (8)0.0062 (9)
C80.0180 (9)0.0197 (10)0.0341 (11)0.0030 (8)0.0061 (8)0.0012 (9)
C90.0247 (9)0.0247 (11)0.0158 (9)0.0038 (8)0.0064 (8)0.0007 (8)
C100.0234 (9)0.0274 (11)0.0209 (9)0.0052 (8)0.0076 (8)0.0015 (8)
C110.0229 (10)0.0364 (12)0.0214 (10)0.0004 (9)0.0081 (8)0.0020 (9)
C120.0252 (10)0.0441 (14)0.0235 (10)0.0113 (10)0.0062 (8)0.0018 (10)
C130.0385 (12)0.0337 (13)0.0253 (10)0.0122 (10)0.0063 (9)0.0062 (9)
C140.0322 (11)0.0319 (12)0.0219 (10)0.0014 (9)0.0084 (8)0.0001 (9)
C150.0251 (10)0.0329 (12)0.0234 (10)0.0058 (9)0.0097 (8)0.0032 (9)
C160.0202 (9)0.0280 (11)0.0224 (10)0.0024 (8)0.0095 (8)0.0001 (8)
C170.0312 (10)0.0437 (14)0.0203 (10)0.0043 (10)0.0015 (9)0.0036 (9)
N10.0216 (8)0.0279 (10)0.0189 (8)0.0001 (7)0.0073 (6)0.0027 (7)
N20.0238 (10)0.0501 (12)0.0303 (9)0.0015 (8)0.0087 (8)0.0019 (9)
O10.0281 (7)0.0252 (8)0.0304 (7)0.0050 (6)0.0064 (6)0.0021 (6)
O20.0233 (7)0.0332 (8)0.0330 (7)0.0019 (6)0.0115 (6)0.0099 (6)
O30.0286 (7)0.0329 (8)0.0195 (7)0.0043 (6)0.0055 (5)0.0004 (6)
O40.0277 (7)0.0409 (9)0.0269 (7)0.0127 (6)0.0089 (6)0.0013 (6)
O50.0323 (8)0.0504 (11)0.0627 (11)0.0065 (8)0.0035 (8)0.0185 (9)
O60.0172 (8)0.0766 (13)0.0680 (11)0.0003 (7)0.0069 (7)0.0113 (9)
Geometric parameters (Å, º) top
C1—O11.406 (2)C11—C121.380 (3)
C1—N11.487 (2)C11—N21.475 (2)
C1—C91.519 (2)C12—C131.375 (3)
C1—C41.519 (2)C12—H120.95
C2—O21.234 (2)C13—C141.390 (3)
C2—N11.357 (2)C13—H130.95
C2—C31.479 (2)C14—H140.95
C3—C81.386 (2)C15—N11.437 (2)
C3—C41.390 (2)C15—C161.518 (2)
C4—C51.383 (2)C15—H15A0.99
C5—C61.390 (2)C15—H15B0.99
C5—H50.95C16—O41.199 (2)
C6—C71.387 (2)C16—O31.331 (2)
C6—H60.95C17—O31.450 (2)
C7—C81.388 (2)C17—H17A0.98
C7—H70.95C17—H17B0.98
C8—H80.95C17—H17C0.98
C9—C101.384 (2)N2—O61.2237 (19)
C9—C141.395 (2)N2—O51.227 (2)
C10—C111.383 (2)O1—H10.84
C10—H100.95
O1—C1—N1110.27 (14)C12—C11—N2118.93 (16)
O1—C1—C9107.16 (14)C10—C11—N2118.28 (17)
N1—C1—C9110.38 (13)C13—C12—C11117.89 (17)
O1—C1—C4113.02 (13)C13—C12—H12121.1
N1—C1—C4100.40 (14)C11—C12—H12121.1
C9—C1—C4115.50 (14)C12—C13—C14120.86 (19)
O2—C2—N1124.84 (17)C12—C13—H13119.6
O2—C2—C3128.57 (17)C14—C13—H13119.6
N1—C2—C3106.56 (15)C13—C14—C9120.35 (19)
C8—C3—C4121.21 (16)C13—C14—H14119.8
C8—C3—C2130.13 (17)C9—C14—H14119.8
C4—C3—C2108.63 (16)N1—C15—C16113.09 (15)
C5—C4—C3121.35 (16)N1—C15—H15A109.0
C5—C4—C1128.45 (16)C16—C15—H15A109.0
C3—C4—C1110.16 (15)N1—C15—H15B109.0
C4—C5—C6117.47 (17)C16—C15—H15B109.0
C4—C5—H5121.3H15A—C15—H15B107.8
C6—C5—H5121.3O4—C16—O3125.69 (16)
C7—C6—C5121.18 (17)O4—C16—C15125.69 (16)
C7—C6—H6119.4O3—C16—C15108.61 (15)
C5—C6—H6119.4O3—C17—H17A109.5
C6—C7—C8121.32 (17)O3—C17—H17B109.5
C6—C7—H7119.3H17A—C17—H17B109.5
C8—C7—H7119.3O3—C17—H17C109.5
C3—C8—C7117.44 (17)H17A—C17—H17C109.5
C3—C8—H8121.3H17B—C17—H17C109.5
C7—C8—H8121.3C2—N1—C15123.72 (15)
C10—C9—C14119.21 (16)C2—N1—C1114.07 (14)
C10—C9—C1120.13 (16)C15—N1—C1122.10 (14)
C14—C9—C1120.61 (16)O6—N2—O5123.01 (17)
C11—C10—C9118.90 (17)O6—N2—C11118.34 (17)
C11—C10—H10120.6O5—N2—C11118.65 (15)
C9—C10—H10120.6C1—O1—H1109.5
C12—C11—C10122.79 (18)C16—O3—C17117.41 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.992.819 (2)171
C5—H5···O3ii0.952.453.371 (2)163
C12—H12···O4iii0.952.383.301 (2)165
Symmetry codes: (i) x, y+2, z; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds