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organic compounds
Two molecules of the title compound, C20H17NO3, are linked by a pair of hydroxy-amide interactions over a center of inversion, giving a hydrogen-bonded dimeric structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000384/bt2237sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000384/bt2237Isup2.hkl |
CCDC reference: 636169
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.118
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg. PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
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 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 1 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: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
2-Ethyl-4-hydroxy-3a,4,9,9a-tetrahydro-4,9-[1',2']benzeno-1H-benz[f]isoindole- 1,3(2H)-dione top
Crystal data top
C20H17NO3 | Z = 2 |
Mr = 319.35 | F(000) = 336 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.743 (2) Å | Cell parameters from 24 reflections |
b = 8.133 (2) Å | θ = 4.7–8.9° |
c = 13.718 (4) Å | µ = 0.09 mm−1 |
α = 74.57 (2)° | T = 295 K |
β = 85.06 (2)° | Block, colorless |
γ = 68.06 (2)° | 0.27 × 0.25 × 0.22 mm |
V = 772.3 (4) Å3 |
Data collection top
Enraf–Nonius CAD-4 four-circle diffractometer | Rint = 0.007 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.5° |
Graphite monochromator | h = −8→9 |
ω–2θ scans | k = −1→9 |
2710 measured reflections | l = −15→16 |
2707 independent reflections | 3 standard reflections every 300 reflections |
1756 reflections with I > 2σ(I) | intensity decay: <1% |
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) = 0.118 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3 |
2707 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.6942 (2) | 0.49190 (19) | 0.58268 (11) | 0.0412 (6) | 0.847 (4) |
H1o | 0.6991 | 0.4862 | 0.5237 | 0.062* | 0.847 (4) |
O1' | 0.9049 (16) | −0.1770 (11) | 0.8390 (7) | 0.060 (4) | 0.153 (4) |
H1' | 0.9439 | −0.2535 | 0.8058 | 0.090* | 0.153 (4) |
O2 | 0.3073 (2) | 0.4748 (2) | 0.62411 (11) | 0.0492 (4) | |
O3 | 0.4867 (2) | −0.0735 (2) | 0.85770 (12) | 0.0615 (5) | |
N1 | 0.3652 (2) | 0.2179 (2) | 0.75456 (12) | 0.0405 (4) | |
C1 | 0.7443 (3) | 0.3162 (2) | 0.64635 (13) | 0.0335 (5) | |
H1 | 0.7131 | 0.4374 | 0.5990 | 0.040* | 0.153 (4) |
C2 | 0.6060 (3) | 0.2191 (2) | 0.63749 (14) | 0.0356 (5) | |
H2 | 0.6058 | 0.2052 | 0.5687 | 0.043* | |
C3 | 0.4109 (3) | 0.3226 (3) | 0.66743 (14) | 0.0369 (5) | |
C4 | 0.1945 (3) | 0.2825 (3) | 0.81063 (17) | 0.0528 (6) | |
H4A | 0.1490 | 0.1833 | 0.8370 | 0.063* | |
H4B | 0.0999 | 0.3809 | 0.7652 | 0.063* | |
C5 | 0.2269 (4) | 0.3503 (4) | 0.89678 (18) | 0.0649 (7) | |
H5A | 0.1126 | 0.3913 | 0.9322 | 0.097* | |
H5B | 0.2695 | 0.4502 | 0.8708 | 0.097* | |
H5C | 0.3192 | 0.2526 | 0.9424 | 0.097* | |
C6 | 0.4997 (3) | 0.0439 (3) | 0.78514 (16) | 0.0424 (5) | |
C7 | 0.6626 (3) | 0.0308 (3) | 0.71462 (14) | 0.0380 (5) | |
H7 | 0.6841 | −0.0665 | 0.6804 | 0.046* | |
C8 | 0.8408 (3) | −0.0048 (3) | 0.77496 (14) | 0.0369 (5) | |
H8 | 0.8811 | −0.1241 | 0.8245 | 0.044* | 0.847 (4) |
C9 | 0.9881 (3) | 0.0115 (3) | 0.69713 (14) | 0.0374 (5) | |
C10 | 1.1587 (3) | −0.1232 (3) | 0.68973 (16) | 0.0463 (6) | |
H10 | 1.1926 | −0.2379 | 0.7352 | 0.056* | |
C11 | 1.2786 (3) | −0.0854 (3) | 0.61388 (17) | 0.0518 (6) | |
H11 | 1.3937 | −0.1755 | 0.6085 | 0.062* | |
C12 | 1.2292 (3) | 0.0841 (3) | 0.54636 (16) | 0.0494 (6) | |
H12 | 1.3119 | 0.1083 | 0.4964 | 0.059* | |
C13 | 1.0563 (3) | 0.2197 (3) | 0.55214 (15) | 0.0423 (5) | |
H13 | 1.0218 | 0.3333 | 0.5055 | 0.051* | |
C14 | 0.9371 (3) | 0.1827 (3) | 0.62821 (14) | 0.0355 (5) | |
C15 | 0.7905 (3) | 0.1526 (2) | 0.82450 (14) | 0.0325 (4) | |
C16 | 0.7861 (3) | 0.1386 (3) | 0.92730 (14) | 0.0404 (5) | |
H16 | 0.8182 | 0.0244 | 0.9733 | 0.048* | |
C17 | 0.7335 (3) | 0.2964 (3) | 0.96102 (16) | 0.0482 (6) | |
H17 | 0.7315 | 0.2878 | 1.0301 | 0.058* | |
C18 | 0.6842 (3) | 0.4655 (3) | 0.89331 (16) | 0.0474 (6) | |
H18 | 0.6500 | 0.5704 | 0.9168 | 0.057* | |
C19 | 0.6853 (3) | 0.4806 (3) | 0.78976 (15) | 0.0380 (5) | |
H19 | 0.6498 | 0.5952 | 0.7440 | 0.046* | |
C20 | 0.7395 (3) | 0.3237 (2) | 0.75579 (13) | 0.0321 (5) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0516 (11) | 0.0303 (10) | 0.0317 (9) | −0.0099 (8) | 0.0055 (8) | −0.0004 (7) |
O1' | 0.076 (8) | 0.045 (6) | 0.043 (6) | −0.010 (6) | −0.002 (5) | −0.003 (5) |
O2 | 0.0436 (9) | 0.0465 (9) | 0.0454 (9) | −0.0051 (7) | −0.0031 (7) | −0.0076 (7) |
O3 | 0.0682 (11) | 0.0554 (10) | 0.0577 (10) | −0.0325 (9) | 0.0044 (8) | 0.0039 (9) |
N1 | 0.0378 (10) | 0.0489 (11) | 0.0370 (9) | −0.0185 (9) | −0.0004 (8) | −0.0103 (8) |
C1 | 0.0378 (11) | 0.0278 (10) | 0.0296 (10) | −0.0091 (9) | 0.0011 (8) | −0.0031 (8) |
C2 | 0.0414 (12) | 0.0360 (11) | 0.0278 (10) | −0.0105 (9) | −0.0017 (8) | −0.0101 (9) |
C3 | 0.0401 (12) | 0.0400 (12) | 0.0310 (10) | −0.0125 (10) | −0.0073 (9) | −0.0101 (9) |
C4 | 0.0327 (12) | 0.0714 (16) | 0.0536 (14) | −0.0214 (11) | 0.0045 (10) | −0.0126 (12) |
C5 | 0.0602 (17) | 0.0843 (19) | 0.0615 (16) | −0.0316 (14) | 0.0181 (13) | −0.0348 (14) |
C6 | 0.0498 (14) | 0.0436 (13) | 0.0401 (12) | −0.0243 (11) | −0.0037 (10) | −0.0088 (10) |
C7 | 0.0451 (12) | 0.0338 (11) | 0.0374 (11) | −0.0148 (10) | −0.0001 (9) | −0.0116 (9) |
C8 | 0.0417 (12) | 0.0280 (10) | 0.0345 (11) | −0.0085 (9) | −0.0001 (9) | −0.0034 (8) |
C9 | 0.0390 (12) | 0.0355 (11) | 0.0365 (11) | −0.0091 (9) | 0.0004 (9) | −0.0136 (9) |
C10 | 0.0453 (13) | 0.0395 (12) | 0.0456 (12) | −0.0022 (10) | −0.0019 (10) | −0.0152 (10) |
C11 | 0.0406 (13) | 0.0582 (15) | 0.0510 (13) | −0.0025 (11) | 0.0038 (11) | −0.0280 (12) |
C12 | 0.0414 (13) | 0.0651 (15) | 0.0435 (13) | −0.0164 (11) | 0.0114 (10) | −0.0246 (12) |
C13 | 0.0448 (13) | 0.0462 (13) | 0.0371 (11) | −0.0153 (10) | 0.0042 (9) | −0.0155 (10) |
C14 | 0.0376 (11) | 0.0364 (11) | 0.0324 (10) | −0.0114 (9) | 0.0030 (9) | −0.0123 (9) |
C15 | 0.0281 (10) | 0.0340 (11) | 0.0327 (10) | −0.0090 (8) | −0.0006 (8) | −0.0072 (8) |
C16 | 0.0369 (12) | 0.0481 (13) | 0.0336 (11) | −0.0154 (10) | −0.0020 (9) | −0.0057 (10) |
C17 | 0.0457 (13) | 0.0683 (16) | 0.0362 (12) | −0.0214 (12) | 0.0045 (10) | −0.0231 (12) |
C18 | 0.0434 (13) | 0.0538 (14) | 0.0516 (13) | −0.0149 (11) | 0.0040 (10) | −0.0293 (12) |
C19 | 0.0339 (11) | 0.0344 (11) | 0.0454 (12) | −0.0099 (9) | 0.0024 (9) | −0.0137 (9) |
C20 | 0.0277 (10) | 0.0346 (11) | 0.0329 (10) | −0.0104 (8) | 0.0028 (8) | −0.0086 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.391 (2) | C7—H7 | 0.9800 |
O1—H1o | 0.8200 | C8—C9 | 1.512 (3) |
O1'—C8 | 1.371 (7) | C8—C15 | 1.516 (3) |
O1'—H1' | 0.8200 | C8—H8 | 0.9800 |
O2—C3 | 1.216 (2) | C9—C10 | 1.382 (3) |
O3—C6 | 1.209 (2) | C9—C14 | 1.394 (3) |
N1—C3 | 1.375 (3) | C10—C11 | 1.384 (3) |
N1—C6 | 1.386 (3) | C10—H10 | 0.9300 |
N1—C4 | 1.461 (3) | C11—C12 | 1.376 (3) |
C1—C20 | 1.515 (3) | C11—H11 | 0.9300 |
C1—C14 | 1.529 (3) | C12—C13 | 1.393 (3) |
C1—C2 | 1.578 (3) | C12—H12 | 0.9300 |
C1—H1 | 0.9800 | C13—C14 | 1.380 (3) |
C2—C3 | 1.512 (3) | C13—H13 | 0.9300 |
C2—C7 | 1.540 (3) | C15—C16 | 1.383 (3) |
C2—H2 | 0.9800 | C15—C20 | 1.392 (3) |
C4—C5 | 1.505 (3) | C16—C17 | 1.386 (3) |
C4—H4A | 0.9700 | C16—H16 | 0.9300 |
C4—H4B | 0.9700 | C17—C18 | 1.374 (3) |
C5—H5A | 0.9600 | C17—H17 | 0.9300 |
C5—H5B | 0.9600 | C18—C19 | 1.392 (3) |
C5—H5C | 0.9600 | C18—H18 | 0.9300 |
C6—C7 | 1.511 (3) | C19—C20 | 1.380 (3) |
C7—C8 | 1.563 (3) | C19—H19 | 0.9300 |
C1—O1—H1o | 109.5 | O1'—C8—C15 | 115.7 (5) |
C8—O1'—H1' | 109.5 | C9—C8—C15 | 108.08 (16) |
C3—N1—C6 | 112.95 (17) | O1'—C8—C7 | 112.1 (5) |
C3—N1—C4 | 124.00 (18) | C9—C8—C7 | 106.26 (16) |
C6—N1—C4 | 123.04 (18) | C15—C8—C7 | 105.65 (15) |
O1—C1—C20 | 110.22 (15) | C9—C8—H8 | 112.1 |
O1—C1—C14 | 115.17 (16) | C15—C8—H8 | 112.1 |
C20—C1—C14 | 107.35 (15) | C7—C8—H8 | 112.1 |
O1—C1—C2 | 112.55 (16) | C10—C9—C14 | 120.15 (19) |
C20—C1—C2 | 106.01 (15) | C10—C9—C8 | 126.57 (18) |
C14—C1—C2 | 104.97 (15) | C14—C9—C8 | 113.28 (17) |
C20—C1—H1 | 112.7 | C9—C10—C11 | 119.3 (2) |
C14—C1—H1 | 112.7 | C9—C10—H10 | 120.3 |
C2—C1—H1 | 112.7 | C11—C10—H10 | 120.3 |
C3—C2—C7 | 104.10 (15) | C12—C11—C10 | 120.6 (2) |
C3—C2—C1 | 111.56 (16) | C12—C11—H11 | 119.7 |
C7—C2—C1 | 109.68 (15) | C10—C11—H11 | 119.7 |
C3—C2—H2 | 110.4 | C11—C12—C13 | 120.6 (2) |
C7—C2—H2 | 110.4 | C11—C12—H12 | 119.7 |
C1—C2—H2 | 110.4 | C13—C12—H12 | 119.7 |
O2—C3—N1 | 123.64 (19) | C14—C13—C12 | 118.9 (2) |
O2—C3—C2 | 127.14 (18) | C14—C13—H13 | 120.5 |
N1—C3—C2 | 109.22 (17) | C12—C13—H13 | 120.5 |
N1—C4—C5 | 111.47 (18) | C13—C14—C9 | 120.47 (19) |
N1—C4—H4A | 109.3 | C13—C14—C1 | 125.72 (18) |
C5—C4—H4A | 109.3 | C9—C14—C1 | 113.81 (17) |
N1—C4—H4B | 109.3 | C16—C15—C20 | 120.26 (18) |
C5—C4—H4B | 109.3 | C16—C15—C8 | 126.16 (17) |
H4A—C4—H4B | 108.0 | C20—C15—C8 | 113.55 (16) |
C4—C5—H5A | 109.5 | C15—C16—C17 | 119.30 (19) |
C4—C5—H5B | 109.5 | C15—C16—H16 | 120.4 |
H5A—C5—H5B | 109.5 | C17—C16—H16 | 120.4 |
C4—C5—H5C | 109.5 | C18—C17—C16 | 120.55 (19) |
H5A—C5—H5C | 109.5 | C18—C17—H17 | 119.7 |
H5B—C5—H5C | 109.5 | C16—C17—H17 | 119.7 |
O3—C6—N1 | 124.5 (2) | C17—C18—C19 | 120.38 (19) |
O3—C6—C7 | 127.0 (2) | C17—C18—H18 | 119.8 |
N1—C6—C7 | 108.42 (17) | C19—C18—H18 | 119.8 |
C6—C7—C2 | 105.04 (16) | C20—C19—C18 | 119.28 (19) |
C6—C7—C8 | 109.92 (16) | C20—C19—H19 | 120.4 |
C2—C7—C8 | 110.08 (15) | C18—C19—H19 | 120.4 |
C6—C7—H7 | 110.6 | C19—C20—C15 | 120.22 (17) |
C2—C7—H7 | 110.6 | C19—C20—C1 | 125.96 (17) |
C8—C7—H7 | 110.6 | C15—C20—C1 | 113.79 (16) |
O1'—C8—C9 | 108.6 (5) | ||
O1—C1—C2—C3 | −61.6 (2) | C14—C9—C10—C11 | 0.6 (3) |
C20—C1—C2—C3 | 58.93 (19) | C8—C9—C10—C11 | −179.6 (2) |
C14—C1—C2—C3 | 172.37 (14) | C9—C10—C11—C12 | 0.0 (3) |
O1—C1—C2—C7 | −176.43 (15) | C10—C11—C12—C13 | −1.0 (3) |
C20—C1—C2—C7 | −55.87 (19) | C11—C12—C13—C14 | 1.5 (3) |
C14—C1—C2—C7 | 57.57 (19) | C12—C13—C14—C9 | −0.9 (3) |
C6—N1—C3—O2 | 175.12 (19) | C12—C13—C14—C1 | 179.13 (19) |
C4—N1—C3—O2 | −5.8 (3) | C10—C9—C14—C13 | −0.1 (3) |
C6—N1—C3—C2 | −5.6 (2) | C8—C9—C14—C13 | −179.90 (18) |
C4—N1—C3—C2 | 173.53 (18) | C10—C9—C14—C1 | 179.85 (18) |
C7—C2—C3—O2 | −175.98 (19) | C8—C9—C14—C1 | 0.0 (2) |
C1—C2—C3—O2 | 65.8 (2) | O1—C1—C14—C13 | −3.9 (3) |
C7—C2—C3—N1 | 4.7 (2) | C20—C1—C14—C13 | −127.0 (2) |
C1—C2—C3—N1 | −113.46 (17) | C2—C1—C14—C13 | 120.5 (2) |
C3—N1—C4—C5 | −96.3 (2) | O1—C1—C14—C9 | 176.19 (16) |
C6—N1—C4—C5 | 82.7 (3) | C20—C1—C14—C9 | 53.0 (2) |
C3—N1—C6—O3 | −177.53 (19) | C2—C1—C14—C9 | −59.4 (2) |
C4—N1—C6—O3 | 3.4 (3) | O1'—C8—C15—C16 | −6.7 (6) |
C3—N1—C6—C7 | 3.9 (2) | C9—C8—C15—C16 | −128.7 (2) |
C4—N1—C6—C7 | −175.20 (18) | C7—C8—C15—C16 | 117.9 (2) |
O3—C6—C7—C2 | −179.2 (2) | O1'—C8—C15—C20 | 175.5 (6) |
N1—C6—C7—C2 | −0.7 (2) | C9—C8—C15—C20 | 53.5 (2) |
O3—C6—C7—C8 | −60.8 (3) | C7—C8—C15—C20 | −59.9 (2) |
N1—C6—C7—C8 | 117.75 (17) | C20—C15—C16—C17 | −1.1 (3) |
C3—C2—C7—C6 | −2.39 (19) | C8—C15—C16—C17 | −178.71 (19) |
C1—C2—C7—C6 | 117.10 (17) | C15—C16—C17—C18 | 0.6 (3) |
C3—C2—C7—C8 | −120.67 (17) | C16—C17—C18—C19 | 0.5 (3) |
C1—C2—C7—C8 | −1.2 (2) | C17—C18—C19—C20 | −1.2 (3) |
C6—C7—C8—O1' | 69.5 (5) | C18—C19—C20—C15 | 0.7 (3) |
C2—C7—C8—O1' | −175.2 (5) | C18—C19—C20—C1 | 178.54 (19) |
C6—C7—C8—C9 | −172.00 (16) | C16—C15—C20—C19 | 0.4 (3) |
C2—C7—C8—C9 | −56.76 (19) | C8—C15—C20—C19 | 178.31 (17) |
C6—C7—C8—C15 | −57.3 (2) | C16—C15—C20—C1 | −177.69 (18) |
C2—C7—C8—C15 | 57.91 (19) | C8—C15—C20—C1 | 0.2 (2) |
O1'—C8—C9—C10 | 0.6 (6) | O1—C1—C20—C19 | 2.9 (3) |
C15—C8—C9—C10 | 126.8 (2) | C14—C1—C20—C19 | 129.03 (19) |
C7—C8—C9—C10 | −120.2 (2) | C2—C1—C20—C19 | −119.2 (2) |
O1'—C8—C9—C14 | −179.6 (5) | O1—C1—C20—C15 | −179.18 (16) |
C15—C8—C9—C14 | −53.4 (2) | C14—C1—C20—C15 | −53.0 (2) |
C7—C8—C9—C14 | 59.6 (2) | C2—C1—C20—C15 | 58.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O2i | 0.82 | 1.97 | 2.778 (2) | 169 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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