organic compounds
The molecule of the title compound, C20H22N2O2, an N-substituted oxindole obtained unexpectedly, is composed of a heterocyclic ring, which adopts an N-envelope conformation, and an isoindole group which is essentially planar.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002097/lh2292sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002097/lh22924asup2.hkl |
CCDC reference: 636747
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.108
- Data-to-parameter ratio = 17.4
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
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: 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).
1-(3,3,5-trimethyl-2-phenyl-1,2-oxazolidin-5-yl)-1H-indol-3(2H)-one top
Crystal data top
C20H22N2O2 | F(000) = 688 |
Mr = 322.40 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6053 reflections |
a = 10.321 (3) Å | θ = 3.5–27.5° |
b = 14.446 (4) Å | µ = 0.08 mm−1 |
c = 11.378 (4) Å | T = 173 K |
β = 98.554 (12)° | Prism, colorless |
V = 1677.6 (9) Å3 | 0.28 × 0.20 × 0.16 mm |
Z = 4 |
Data collection top
Nonius KappaCCD diffractometer | 3825 independent reflections |
Radiation source: fine-focus sealed tube | 2632 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω and φ scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −11→13 |
Tmin = 0.977, Tmax = 0.987 | k = −17→18 |
6053 measured reflections | l = −14→14 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.104P] where P = (Fo2 + 2Fc2)/3 |
3825 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.32076 (8) | 0.06343 (6) | −0.02365 (7) | 0.0251 (2) | |
O2 | 0.11403 (9) | 0.04877 (7) | −0.37098 (8) | 0.0343 (3) | |
N1 | 0.20768 (9) | 0.06345 (7) | 0.04153 (9) | 0.0226 (3) | |
N2 | 0.22364 (10) | −0.01500 (8) | −0.19824 (9) | 0.0244 (3) | |
C1 | 0.26463 (12) | 0.07637 (9) | −0.14353 (11) | 0.0241 (3) | |
C2 | 0.14409 (12) | 0.13848 (10) | −0.13813 (12) | 0.0273 (3) | |
H2A | 0.1544 | 0.1989 | −0.1767 | 0.033* | |
H2B | 0.0633 | 0.1083 | −0.1782 | 0.033* | |
C3 | 0.13877 (12) | 0.15100 (9) | −0.00516 (11) | 0.0245 (3) | |
C4 | 0.37133 (12) | 0.11751 (10) | −0.20610 (12) | 0.0299 (3) | |
H4A | 0.3398 | 0.1219 | −0.2915 | 0.036* | |
H4B | 0.4491 | 0.0778 | −0.1929 | 0.036* | |
H4C | 0.3939 | 0.1794 | −0.1743 | 0.036* | |
C5 | −0.00048 (12) | 0.15053 (10) | 0.02358 (13) | 0.0323 (3) | |
H5A | −0.0502 | 0.2014 | −0.0187 | 0.039* | |
H5B | 0.0015 | 0.1585 | 0.1094 | 0.039* | |
H5C | −0.0425 | 0.0915 | −0.0014 | 0.039* | |
C6 | 0.21117 (13) | 0.23798 (10) | 0.04388 (13) | 0.0322 (3) | |
H6A | 0.1666 | 0.2927 | 0.0064 | 0.039* | |
H6B | 0.3014 | 0.2361 | 0.0267 | 0.039* | |
H6C | 0.2120 | 0.2410 | 0.1300 | 0.039* | |
C7 | 0.25868 (12) | 0.06192 (9) | 0.16572 (11) | 0.0238 (3) | |
C8 | 0.17162 (13) | 0.03570 (10) | 0.24268 (12) | 0.0300 (3) | |
H8 | 0.0845 | 0.0182 | 0.2114 | 0.036* | |
C9 | 0.21170 (15) | 0.03505 (10) | 0.36421 (13) | 0.0351 (4) | |
H9 | 0.1512 | 0.0195 | 0.4163 | 0.042* | |
C10 | 0.33994 (15) | 0.05701 (11) | 0.41012 (13) | 0.0369 (4) | |
H10 | 0.3678 | 0.0561 | 0.4935 | 0.044* | |
C11 | 0.42687 (14) | 0.08027 (10) | 0.33391 (13) | 0.0350 (4) | |
H11 | 0.5152 | 0.0941 | 0.3653 | 0.042* | |
C12 | 0.38697 (13) | 0.08371 (10) | 0.21185 (12) | 0.0298 (3) | |
H12 | 0.4473 | 0.1009 | 0.1603 | 0.036* | |
C13 | 0.15714 (12) | −0.01865 (10) | −0.31306 (12) | 0.0276 (3) | |
C14 | 0.14893 (14) | −0.11871 (10) | −0.35257 (13) | 0.0345 (3) | |
H14A | 0.0570 | −0.1405 | −0.3662 | 0.041* | |
H14B | 0.1877 | −0.1273 | −0.4264 | 0.041* | |
C15 | 0.22670 (13) | −0.16867 (10) | −0.25062 (12) | 0.0302 (3) | |
C16 | 0.25781 (14) | −0.26120 (11) | −0.23552 (14) | 0.0397 (4) | |
H16 | 0.2292 | −0.3046 | −0.2967 | 0.048* | |
C17 | 0.33152 (15) | −0.29019 (11) | −0.12971 (15) | 0.0434 (4) | |
H17 | 0.3546 | −0.3536 | −0.1187 | 0.052* | |
C18 | 0.37126 (14) | −0.22708 (11) | −0.04071 (14) | 0.0372 (4) | |
H18 | 0.4208 | −0.2481 | 0.0314 | 0.045* | |
C19 | 0.34072 (12) | −0.13343 (10) | −0.05376 (13) | 0.0302 (3) | |
H19 | 0.3680 | −0.0906 | 0.0083 | 0.036* | |
C20 | 0.26919 (11) | −0.10490 (9) | −0.16041 (11) | 0.0247 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0248 (4) | 0.0323 (6) | 0.0191 (5) | 0.0012 (4) | 0.0059 (4) | −0.0016 (4) |
O2 | 0.0445 (6) | 0.0341 (6) | 0.0233 (5) | 0.0010 (5) | 0.0021 (4) | 0.0012 (5) |
N1 | 0.0248 (5) | 0.0238 (6) | 0.0204 (6) | 0.0008 (4) | 0.0070 (4) | −0.0003 (5) |
N2 | 0.0294 (5) | 0.0240 (6) | 0.0198 (6) | 0.0002 (5) | 0.0033 (4) | −0.0009 (5) |
C1 | 0.0275 (6) | 0.0259 (8) | 0.0188 (7) | −0.0004 (5) | 0.0031 (5) | −0.0005 (5) |
C2 | 0.0301 (7) | 0.0275 (8) | 0.0242 (7) | 0.0020 (6) | 0.0039 (5) | 0.0000 (6) |
C3 | 0.0289 (6) | 0.0211 (7) | 0.0240 (7) | 0.0003 (5) | 0.0051 (5) | −0.0002 (6) |
C4 | 0.0318 (7) | 0.0318 (8) | 0.0267 (7) | −0.0029 (6) | 0.0066 (5) | 0.0006 (6) |
C5 | 0.0303 (7) | 0.0338 (8) | 0.0338 (8) | 0.0041 (6) | 0.0083 (6) | 0.0018 (7) |
C6 | 0.0398 (7) | 0.0240 (8) | 0.0327 (8) | −0.0012 (6) | 0.0052 (6) | −0.0012 (6) |
C7 | 0.0305 (7) | 0.0193 (7) | 0.0218 (7) | 0.0012 (5) | 0.0042 (5) | −0.0020 (5) |
C8 | 0.0332 (7) | 0.0308 (8) | 0.0271 (8) | −0.0001 (6) | 0.0079 (6) | 0.0017 (6) |
C9 | 0.0469 (8) | 0.0328 (9) | 0.0283 (8) | 0.0069 (7) | 0.0141 (6) | 0.0045 (7) |
C10 | 0.0537 (9) | 0.0356 (9) | 0.0208 (7) | 0.0125 (7) | 0.0033 (6) | 0.0000 (6) |
C11 | 0.0367 (7) | 0.0364 (9) | 0.0295 (8) | 0.0029 (6) | −0.0028 (6) | −0.0044 (7) |
C12 | 0.0320 (7) | 0.0318 (8) | 0.0258 (7) | −0.0004 (6) | 0.0053 (5) | −0.0016 (6) |
C13 | 0.0309 (7) | 0.0314 (8) | 0.0211 (7) | −0.0011 (6) | 0.0060 (5) | −0.0021 (6) |
C14 | 0.0426 (8) | 0.0317 (9) | 0.0290 (8) | −0.0024 (7) | 0.0042 (6) | −0.0078 (7) |
C15 | 0.0328 (7) | 0.0280 (8) | 0.0310 (8) | −0.0028 (6) | 0.0086 (6) | −0.0035 (6) |
C16 | 0.0449 (8) | 0.0285 (8) | 0.0457 (10) | −0.0030 (7) | 0.0069 (7) | −0.0067 (7) |
C17 | 0.0457 (9) | 0.0280 (9) | 0.0565 (11) | 0.0007 (7) | 0.0078 (8) | 0.0046 (8) |
C18 | 0.0360 (7) | 0.0324 (9) | 0.0422 (9) | 0.0005 (6) | 0.0025 (6) | 0.0088 (7) |
C19 | 0.0295 (7) | 0.0308 (8) | 0.0306 (8) | −0.0023 (6) | 0.0053 (6) | 0.0019 (6) |
C20 | 0.0241 (6) | 0.0230 (7) | 0.0284 (7) | −0.0012 (5) | 0.0086 (5) | 0.0019 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.4128 (15) | C7—C8 | 1.3970 (18) |
O1—N1 | 1.4730 (13) | C8—C9 | 1.383 (2) |
O2—C13 | 1.2221 (17) | C8—H8 | 0.9500 |
N1—C7 | 1.4328 (17) | C9—C10 | 1.386 (2) |
N1—C3 | 1.5083 (17) | C9—H9 | 0.9500 |
N2—C13 | 1.3834 (17) | C10—C11 | 1.379 (2) |
N2—C20 | 1.4257 (17) | C10—H10 | 0.9500 |
N2—C1 | 1.4934 (18) | C11—C12 | 1.390 (2) |
C1—C4 | 1.5186 (17) | C11—H11 | 0.9500 |
C1—C2 | 1.5426 (18) | C12—H12 | 0.9500 |
C2—C3 | 1.5328 (19) | C13—C14 | 1.512 (2) |
C2—H2A | 0.9900 | C14—C15 | 1.495 (2) |
C2—H2B | 0.9900 | C14—H14A | 0.9900 |
C3—C5 | 1.5206 (18) | C14—H14B | 0.9900 |
C3—C6 | 1.5247 (19) | C15—C16 | 1.379 (2) |
C4—H4A | 0.9800 | C15—C20 | 1.4003 (19) |
C4—H4B | 0.9800 | C16—C17 | 1.390 (2) |
C4—H4C | 0.9800 | C16—H16 | 0.9500 |
C5—H5A | 0.9800 | C17—C18 | 1.379 (2) |
C5—H5B | 0.9800 | C17—H17 | 0.9500 |
C5—H5C | 0.9800 | C18—C19 | 1.392 (2) |
C6—H6A | 0.9800 | C18—H18 | 0.9500 |
C6—H6B | 0.9800 | C19—C20 | 1.3860 (19) |
C6—H6C | 0.9800 | C19—H19 | 0.9500 |
C7—C12 | 1.3860 (19) | ||
C1—O1—N1 | 104.14 (8) | C12—C7—N1 | 124.06 (11) |
C7—N1—O1 | 107.11 (9) | C8—C7—N1 | 116.50 (11) |
C7—N1—C3 | 116.43 (10) | C9—C8—C7 | 120.26 (13) |
O1—N1—C3 | 100.97 (9) | C9—C8—H8 | 119.9 |
C13—N2—C20 | 110.21 (11) | C7—C8—H8 | 119.9 |
C13—N2—C1 | 119.82 (11) | C8—C9—C10 | 120.15 (13) |
C20—N2—C1 | 128.24 (10) | C8—C9—H9 | 119.9 |
O1—C1—N2 | 109.60 (10) | C10—C9—H9 | 119.9 |
O1—C1—C4 | 106.42 (10) | C11—C10—C9 | 119.54 (14) |
N2—C1—C4 | 109.32 (10) | C11—C10—H10 | 120.2 |
O1—C1—C2 | 104.82 (10) | C9—C10—H10 | 120.2 |
N2—C1—C2 | 110.52 (10) | C10—C11—C12 | 120.89 (14) |
C4—C1—C2 | 115.87 (11) | C10—C11—H11 | 119.6 |
C3—C2—C1 | 104.80 (10) | C12—C11—H11 | 119.6 |
C3—C2—H2A | 110.8 | C7—C12—C11 | 119.65 (12) |
C1—C2—H2A | 110.8 | C7—C12—H12 | 120.2 |
C3—C2—H2B | 110.8 | C11—C12—H12 | 120.2 |
C1—C2—H2B | 110.8 | O2—C13—N2 | 124.65 (13) |
H2A—C2—H2B | 108.9 | O2—C13—C14 | 126.98 (13) |
N1—C3—C5 | 109.37 (10) | N2—C13—C14 | 108.37 (12) |
N1—C3—C6 | 112.48 (11) | C15—C14—C13 | 103.35 (11) |
C5—C3—C6 | 110.64 (11) | C15—C14—H14A | 111.1 |
N1—C3—C2 | 99.47 (10) | C13—C14—H14A | 111.1 |
C5—C3—C2 | 112.67 (11) | C15—C14—H14B | 111.1 |
C6—C3—C2 | 111.77 (11) | C13—C14—H14B | 111.1 |
C1—C4—H4A | 109.5 | H14A—C14—H14B | 109.1 |
C1—C4—H4B | 109.5 | C16—C15—C20 | 120.30 (14) |
H4A—C4—H4B | 109.5 | C16—C15—C14 | 130.75 (14) |
C1—C4—H4C | 109.5 | C20—C15—C14 | 108.95 (13) |
H4A—C4—H4C | 109.5 | C15—C16—C17 | 119.15 (15) |
H4B—C4—H4C | 109.5 | C15—C16—H16 | 120.4 |
C3—C5—H5A | 109.5 | C17—C16—H16 | 120.4 |
C3—C5—H5B | 109.5 | C18—C17—C16 | 120.12 (15) |
H5A—C5—H5B | 109.5 | C18—C17—H17 | 119.9 |
C3—C5—H5C | 109.5 | C16—C17—H17 | 119.9 |
H5A—C5—H5C | 109.5 | C17—C18—C19 | 121.76 (15) |
H5B—C5—H5C | 109.5 | C17—C18—H18 | 119.1 |
C3—C6—H6A | 109.5 | C19—C18—H18 | 119.1 |
C3—C6—H6B | 109.5 | C20—C19—C18 | 117.71 (14) |
H6A—C6—H6B | 109.5 | C20—C19—H19 | 121.1 |
C3—C6—H6C | 109.5 | C18—C19—H19 | 121.1 |
H6A—C6—H6C | 109.5 | C19—C20—C15 | 120.94 (13) |
H6B—C6—H6C | 109.5 | C19—C20—N2 | 130.09 (12) |
C12—C7—C8 | 119.44 (13) | C15—C20—N2 | 108.95 (12) |
C1—O1—N1—C7 | −173.08 (10) | C7—C8—C9—C10 | −2.5 (2) |
C1—O1—N1—C3 | −50.81 (11) | C8—C9—C10—C11 | 0.6 (2) |
N1—O1—C1—N2 | −85.70 (10) | C9—C10—C11—C12 | 1.3 (2) |
N1—O1—C1—C4 | 156.20 (10) | C8—C7—C12—C11 | −0.8 (2) |
N1—O1—C1—C2 | 32.93 (12) | N1—C7—C12—C11 | 179.90 (13) |
C13—N2—C1—O1 | 175.20 (9) | C10—C11—C12—C7 | −1.1 (2) |
C20—N2—C1—O1 | −21.35 (15) | C20—N2—C13—O2 | −175.45 (12) |
C13—N2—C1—C4 | −68.51 (14) | C1—N2—C13—O2 | −9.25 (18) |
C20—N2—C1—C4 | 94.93 (14) | C20—N2—C13—C14 | 4.16 (13) |
C13—N2—C1—C2 | 60.16 (14) | C1—N2—C13—C14 | 170.37 (10) |
C20—N2—C1—C2 | −136.39 (12) | O2—C13—C14—C15 | 175.51 (12) |
O1—C1—C2—C3 | −3.43 (13) | N2—C13—C14—C15 | −4.10 (14) |
N2—C1—C2—C3 | 114.58 (11) | C13—C14—C15—C16 | −177.97 (14) |
C4—C1—C2—C3 | −120.39 (12) | C13—C14—C15—C20 | 2.61 (14) |
C7—N1—C3—C5 | −80.50 (13) | C20—C15—C16—C17 | 0.1 (2) |
O1—N1—C3—C5 | 163.97 (10) | C14—C15—C16—C17 | −179.23 (14) |
C7—N1—C3—C6 | 42.86 (14) | C15—C16—C17—C18 | 0.8 (2) |
O1—N1—C3—C6 | −72.67 (12) | C16—C17—C18—C19 | −0.7 (2) |
C7—N1—C3—C2 | 161.28 (10) | C17—C18—C19—C20 | −0.5 (2) |
O1—N1—C3—C2 | 45.75 (10) | C18—C19—C20—C15 | 1.46 (18) |
C1—C2—C3—N1 | −26.08 (12) | C18—C19—C20—N2 | 179.55 (12) |
C1—C2—C3—C5 | −141.81 (12) | C16—C15—C20—C19 | −1.31 (19) |
C1—C2—C3—C6 | 92.87 (13) | C14—C15—C20—C19 | 178.18 (11) |
O1—N1—C7—C12 | 16.82 (16) | C16—C15—C20—N2 | −179.76 (11) |
C3—N1—C7—C12 | −95.22 (15) | C14—C15—C20—N2 | −0.27 (14) |
O1—N1—C7—C8 | −162.54 (11) | C13—N2—C20—C19 | 179.24 (12) |
C3—N1—C7—C8 | 85.42 (14) | C1—N2—C20—C19 | 14.5 (2) |
C12—C7—C8—C9 | 2.6 (2) | C13—N2—C20—C15 | −2.49 (13) |
N1—C7—C8—C9 | −178.05 (12) | C1—N2—C20—C15 | −167.22 (11) |