Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056929/lh2558sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056929/lh2558Isup2.hkl |
CCDC reference: 672953
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.097
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check
For related literature, see: Benati et al. (2003); Berger et al. (1999); Bernstein et al. (1994); Cignarella et al. (1981); Mancilla et al. (2007).
A mixture of o-phthaldehyde (0.67 g, 200 mmol) and N-phenylurea (0.68 g, 200 mmol) in 100 ml of ethanol was refluxed for 12 hrs. The contents of flask were then left to stand for 48 hrs. at room temperature. The crystals of (I) thus formed were filtered, washed with hexane, ether and ethanol and were dried at room temperature. Crystals suitable for X-ray diffraction were grown from a solution of acetone by slow evaporation at room temperature.
H-atoms were included in the refinements at geometrically idealized positions with C—Haromatic = 0.95, CH2 = 0.99 and N—H = 0.88 Å and Uiso = 1.2 times Ueq of the atoms to which they were bonded. The final difference map was free of any chemically significant features.
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C15H12N2O2 | F(000) = 528 |
Mr = 252.27 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5034 reflections |
a = 12.905 (4) Å | θ = 2.6–27.5° |
b = 5.619 (1) Å | µ = 0.09 mm−1 |
c = 17.161 (6) Å | T = 173 K |
β = 102.228 (17)° | Needle, colorless |
V = 1216.2 (6) Å3 | 0.35 × 0.10 × 0.06 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2768 independent reflections |
Radiation source: fine-focus sealed tube | 2119 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω and ϕ scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −16→16 |
Tmin = 0.968, Tmax = 0.994 | k = −6→7 |
5034 measured reflections | l = −22→22 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.038P)2 + 0.39P] where P = (Fo2 + 2Fc2)/3 |
2768 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C15H12N2O2 | V = 1216.2 (6) Å3 |
Mr = 252.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.905 (4) Å | µ = 0.09 mm−1 |
b = 5.619 (1) Å | T = 173 K |
c = 17.161 (6) Å | 0.35 × 0.10 × 0.06 mm |
β = 102.228 (17)° |
Nonius KappaCCD diffractometer | 2768 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 2119 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.994 | Rint = 0.021 |
5034 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
2768 reflections | Δρmin = −0.16 e Å−3 |
172 parameters |
Experimental. IR spectra (nujol) showed vibrations 3425 cm-1 (N—H), 1714 and 1680 cm-1 (C=O), 1600 and 155.8 cm-1 (C=C), 1150 cm-1 (C—O). 1H-NMR (DMSO-d6); δ: 4.92 (s –CH2–), 7.10–7.93 (aromatic ring protons, 9H), 10.72 (s, NH). 13C-NMR (DMSO-d6); δ: 48.59 (–CH2–), 123.37 (C4), 124.08 (C3), 128.65 (C5), 130.94 (C6), 133.93 (C2), 141.07 (C1), 150.25 (C9), 169.44 (C8) and 120.06, 124.86, 129.03, 137.50 (N—Ph carbons). Anal. Calcd for C15H12N2O2. Required: C, 71.42; H, 4.79; N, 11.0; O, 12.68; Found: C, 71.40; H, 4.80; N, 11.07; O, 12.70. m.p. 441 K. m/z; 252. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.92562 (7) | −0.27832 (16) | 0.39885 (5) | 0.0328 (2) | |
O2 | 0.89390 (8) | 0.31349 (17) | 0.24855 (6) | 0.0406 (3) | |
N1 | 0.97796 (8) | 0.07840 (18) | 0.34984 (6) | 0.0263 (2) | |
N2 | 0.80821 (8) | −0.01677 (19) | 0.28210 (6) | 0.0297 (3) | |
H2N | 0.8169 | −0.1366 | 0.3159 | 0.036* | |
C1 | 1.09874 (10) | −0.1015 (2) | 0.44905 (7) | 0.0268 (3) | |
C2 | 1.14801 (11) | −0.2514 (2) | 0.51004 (8) | 0.0315 (3) | |
H2 | 1.1139 | −0.3908 | 0.5234 | 0.038* | |
C3 | 1.24880 (11) | −0.1894 (3) | 0.55062 (8) | 0.0356 (3) | |
H3 | 1.2846 | −0.2866 | 0.5932 | 0.043* | |
C4 | 1.29830 (11) | 0.0143 (3) | 0.52972 (8) | 0.0380 (3) | |
H4 | 1.3676 | 0.0532 | 0.5584 | 0.046* | |
C5 | 1.24877 (11) | 0.1619 (2) | 0.46793 (8) | 0.0346 (3) | |
H5 | 1.2834 | 0.2991 | 0.4535 | 0.041* | |
C6 | 1.14717 (10) | 0.1021 (2) | 0.42818 (7) | 0.0281 (3) | |
C7 | 1.07353 (10) | 0.2269 (2) | 0.36116 (8) | 0.0296 (3) | |
H7A | 1.0587 | 0.3916 | 0.3761 | 0.036* | |
H7B | 1.1030 | 0.2308 | 0.3124 | 0.036* | |
C8 | 0.99162 (10) | −0.1207 (2) | 0.39860 (7) | 0.0263 (3) | |
C9 | 0.89044 (10) | 0.1374 (2) | 0.28902 (7) | 0.0284 (3) | |
C10 | 0.71058 (10) | −0.0067 (2) | 0.22699 (8) | 0.0301 (3) | |
C11 | 0.68394 (11) | 0.1681 (3) | 0.16870 (8) | 0.0360 (3) | |
H11 | 0.7324 | 0.2927 | 0.1648 | 0.043* | |
C12 | 0.58577 (11) | 0.1588 (3) | 0.11620 (9) | 0.0419 (4) | |
H12 | 0.5675 | 0.2784 | 0.0765 | 0.050* | |
C13 | 0.51455 (12) | −0.0206 (3) | 0.12064 (9) | 0.0452 (4) | |
H13 | 0.4481 | −0.0259 | 0.0840 | 0.054* | |
C14 | 0.54067 (12) | −0.1927 (3) | 0.17890 (10) | 0.0480 (4) | |
H14 | 0.4916 | −0.3158 | 0.1828 | 0.058* | |
C15 | 0.63785 (11) | −0.1869 (3) | 0.23162 (9) | 0.0401 (3) | |
H15 | 0.6552 | −0.3067 | 0.2713 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0361 (5) | 0.0257 (5) | 0.0383 (5) | −0.0031 (4) | 0.0116 (4) | 0.0042 (4) |
O2 | 0.0453 (6) | 0.0332 (5) | 0.0402 (6) | −0.0068 (4) | 0.0016 (4) | 0.0125 (4) |
N1 | 0.0310 (6) | 0.0215 (5) | 0.0280 (5) | −0.0004 (4) | 0.0093 (4) | 0.0015 (4) |
N2 | 0.0330 (6) | 0.0276 (5) | 0.0290 (6) | −0.0025 (4) | 0.0080 (4) | 0.0037 (4) |
C1 | 0.0315 (6) | 0.0226 (6) | 0.0286 (6) | 0.0032 (5) | 0.0119 (5) | −0.0018 (5) |
C2 | 0.0375 (7) | 0.0267 (6) | 0.0328 (7) | 0.0051 (5) | 0.0131 (6) | 0.0026 (5) |
C3 | 0.0383 (7) | 0.0360 (7) | 0.0333 (7) | 0.0105 (6) | 0.0094 (6) | 0.0028 (6) |
C4 | 0.0322 (7) | 0.0410 (8) | 0.0398 (8) | 0.0035 (6) | 0.0054 (6) | −0.0033 (6) |
C5 | 0.0349 (7) | 0.0296 (7) | 0.0403 (8) | −0.0023 (6) | 0.0105 (6) | −0.0016 (6) |
C6 | 0.0330 (7) | 0.0237 (6) | 0.0296 (7) | 0.0019 (5) | 0.0113 (5) | −0.0023 (5) |
C7 | 0.0336 (7) | 0.0223 (6) | 0.0336 (7) | −0.0033 (5) | 0.0084 (5) | 0.0006 (5) |
C8 | 0.0340 (7) | 0.0200 (6) | 0.0281 (6) | 0.0025 (5) | 0.0139 (5) | −0.0004 (5) |
C9 | 0.0347 (7) | 0.0248 (6) | 0.0272 (6) | 0.0002 (5) | 0.0097 (5) | −0.0012 (5) |
C10 | 0.0314 (7) | 0.0302 (6) | 0.0302 (7) | 0.0011 (5) | 0.0100 (5) | −0.0036 (5) |
C11 | 0.0335 (7) | 0.0347 (7) | 0.0406 (8) | −0.0003 (6) | 0.0092 (6) | 0.0050 (6) |
C12 | 0.0356 (7) | 0.0448 (8) | 0.0444 (8) | 0.0033 (6) | 0.0067 (6) | 0.0085 (7) |
C13 | 0.0339 (8) | 0.0493 (9) | 0.0494 (9) | −0.0019 (7) | 0.0024 (7) | 0.0009 (7) |
C14 | 0.0407 (8) | 0.0425 (8) | 0.0583 (10) | −0.0122 (7) | 0.0048 (7) | 0.0028 (7) |
C15 | 0.0419 (8) | 0.0341 (7) | 0.0434 (8) | −0.0063 (6) | 0.0070 (7) | 0.0043 (6) |
O1—C8 | 1.2293 (15) | C5—C6 | 1.3851 (19) |
O2—C9 | 1.2148 (16) | C5—H5 | 0.9500 |
N1—C8 | 1.3859 (15) | C6—C7 | 1.5016 (18) |
N1—C9 | 1.4057 (17) | C7—H7A | 0.9900 |
N1—C7 | 1.4676 (16) | C7—H7B | 0.9900 |
N2—C9 | 1.3556 (16) | C10—C11 | 1.3921 (19) |
N2—C10 | 1.4073 (17) | C10—C15 | 1.3944 (19) |
N2—H2N | 0.8800 | C11—C12 | 1.391 (2) |
C1—C6 | 1.3865 (17) | C11—H11 | 0.9500 |
C1—C2 | 1.3883 (18) | C12—C13 | 1.377 (2) |
C1—C8 | 1.4715 (18) | C12—H12 | 0.9500 |
C2—C3 | 1.384 (2) | C13—C14 | 1.380 (2) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.394 (2) | C14—C15 | 1.383 (2) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.391 (2) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | ||
C8—N1—C9 | 128.19 (10) | N1—C7—H7B | 111.3 |
C8—N1—C7 | 112.54 (10) | C6—C7—H7B | 111.3 |
C9—N1—C7 | 118.99 (10) | H7A—C7—H7B | 109.2 |
C9—N2—C10 | 127.29 (11) | O1—C8—N1 | 125.74 (12) |
C9—N2—H2N | 116.4 | O1—C8—C1 | 128.03 (11) |
C10—N2—H2N | 116.4 | N1—C8—C1 | 106.22 (10) |
C6—C1—C2 | 122.40 (12) | O2—C9—N2 | 126.40 (12) |
C6—C1—C8 | 109.11 (11) | O2—C9—N1 | 119.71 (12) |
C2—C1—C8 | 128.47 (12) | N2—C9—N1 | 113.89 (11) |
C3—C2—C1 | 117.27 (12) | C11—C10—C15 | 119.12 (13) |
C3—C2—H2 | 121.4 | C11—C10—N2 | 124.12 (12) |
C1—C2—H2 | 121.4 | C15—C10—N2 | 116.75 (12) |
C2—C3—C4 | 120.69 (13) | C12—C11—C10 | 119.41 (13) |
C2—C3—H3 | 119.7 | C12—C11—H11 | 120.3 |
C4—C3—H3 | 119.7 | C10—C11—H11 | 120.3 |
C5—C4—C3 | 121.61 (13) | C13—C12—C11 | 121.24 (14) |
C5—C4—H4 | 119.2 | C13—C12—H12 | 119.4 |
C3—C4—H4 | 119.2 | C11—C12—H12 | 119.4 |
C6—C5—C4 | 117.71 (13) | C12—C13—C14 | 119.29 (14) |
C6—C5—H5 | 121.1 | C12—C13—H13 | 120.4 |
C4—C5—H5 | 121.1 | C14—C13—H13 | 120.4 |
C5—C6—C1 | 120.30 (12) | C13—C14—C15 | 120.41 (14) |
C5—C6—C7 | 130.05 (12) | C13—C14—H14 | 119.8 |
C1—C6—C7 | 109.66 (11) | C15—C14—H14 | 119.8 |
N1—C7—C6 | 102.34 (10) | C14—C15—C10 | 120.52 (14) |
N1—C7—H7A | 111.3 | C14—C15—H15 | 119.7 |
C6—C7—H7A | 111.3 | C10—C15—H15 | 119.7 |
C6—C1—C2—C3 | 0.42 (18) | C2—C1—C8—O1 | −2.6 (2) |
C8—C1—C2—C3 | −177.84 (12) | C6—C1—C8—N1 | −1.61 (13) |
C1—C2—C3—C4 | −0.79 (19) | C2—C1—C8—N1 | 176.84 (12) |
C2—C3—C4—C5 | 0.1 (2) | C10—N2—C9—O2 | 0.3 (2) |
C3—C4—C5—C6 | 1.0 (2) | C10—N2—C9—N1 | −179.59 (11) |
C4—C5—C6—C1 | −1.35 (19) | C8—N1—C9—O2 | −175.71 (12) |
C4—C5—C6—C7 | 178.64 (13) | C7—N1—C9—O2 | −2.24 (17) |
C2—C1—C6—C5 | 0.67 (19) | C8—N1—C9—N2 | 4.20 (17) |
C8—C1—C6—C5 | 179.23 (11) | C7—N1—C9—N2 | 177.67 (10) |
C2—C1—C6—C7 | −179.32 (11) | C9—N2—C10—C11 | 0.9 (2) |
C8—C1—C6—C7 | −0.76 (13) | C9—N2—C10—C15 | −179.93 (12) |
C8—N1—C7—C6 | −3.79 (13) | C15—C10—C11—C12 | −0.3 (2) |
C9—N1—C7—C6 | −178.24 (10) | N2—C10—C11—C12 | 178.82 (13) |
C5—C6—C7—N1 | −177.34 (13) | C10—C11—C12—C13 | −0.2 (2) |
C1—C6—C7—N1 | 2.65 (13) | C11—C12—C13—C14 | 0.8 (2) |
C9—N1—C8—O1 | −3.3 (2) | C12—C13—C14—C15 | −0.8 (3) |
C7—N1—C8—O1 | −177.10 (12) | C13—C14—C15—C10 | 0.3 (2) |
C9—N1—C8—C1 | 177.28 (11) | C11—C10—C15—C14 | 0.2 (2) |
C7—N1—C8—C1 | 3.46 (13) | N2—C10—C15—C14 | −178.95 (13) |
C6—C1—C8—O1 | 178.97 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.95 | 2.41 | 3.3105 (17) | 159 |
C7—H7B···O2ii | 0.99 | 2.57 | 3.0746 (17) | 112 |
C7—H7B···N2iii | 0.99 | 2.60 | 3.4695 (18) | 147 |
C11—H11···O2 | 0.95 | 2.27 | 2.8833 (19) | 122 |
N2—H2N···O1 | 0.88 | 1.95 | 2.6803 (15) | 140 |
Symmetry codes: (i) −x+2, −y−1, −z+1; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12N2O2 |
Mr | 252.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 12.905 (4), 5.619 (1), 17.161 (6) |
β (°) | 102.228 (17) |
V (Å3) | 1216.2 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.968, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5034, 2768, 2119 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.097, 1.02 |
No. of reflections | 2768 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.95 | 2.41 | 3.3105 (17) | 159.1 |
C7—H7B···O2ii | 0.99 | 2.57 | 3.0746 (17) | 111.5 |
C7—H7B···N2iii | 0.99 | 2.60 | 3.4695 (18) | 147.1 |
C11—H11···O2 | 0.95 | 2.27 | 2.8833 (19) | 121.5 |
N2—H2N···O1 | 0.88 | 1.95 | 2.6803 (15) | 140.0 |
Symmetry codes: (i) −x+2, −y−1, −z+1; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2. |
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Isoindole type compounds are important as intermediates for the synthesis of novel multidrugs resistance reversal agents (Berger et al., 1999). They have also shown diuretic activity (Cignarella et al., 1981). Several isoindoles have exhibited anti-inflammatory and analgesic activity (Mancilla et al., 2007). In our efforts to isolate chromagens responsible for color development in the reaction of N-phenylurea with ortho phthaldehyde (OPTA), the title compound, (I), was prepared, the crystal structure of which is presented in this article.
The structure of (I) is composed of an essentially planar molecule comprised of an isoindole ring that is briged through a carboxamide group to a phenyl ring (Fig. 1). A mean-planes calculation through all non-hydrogen atoms revealed that C12 and N1 atoms lie 0.057 (1) and 0.052 (1) Å above and below, respectively, from the plane. The angle between mean-planes of the isoindole ring and the phenyl ring is 2.62 (8)°. The structure is stabilized by two intramolecular hydrogen bonds N2—H2N···O1 and C11—H11A···O2 that result in six membered rings which may be best defined in graph set patterns S(6) (Bernstein et al., 1994); details of hydrogen bonding geometry have been provided in the Table. In addition, rather weak intermolecular interactions of two distinct types are present in the crystal (Fig. 2). The C—H···O type intermolecular H-bonding results in dimers forming ten-membered rings ···O1—C8—C1—C2—H2···O1i and ···O2—C9—N1—C7—H7b···O2ii, both representing R22(10) graph set patterns (Bernstein et al., 1994). The C—H···N type H-bonding results in chains of molecules in a pattern ···N2—C9—N1—C7—H7B···N2iii along the b-aixs. Symmetry codes as in the bydrogen bond geometry table.
The structure of 2-(bis(1-oxo-2,3-dihydroisoindol-2-yl)methyl)tetrahydrothiophene (Benati et al., 2003) which is somewhat related to the title compound has been reported.