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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000384/bt2237sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000384/bt2237Isup2.hkl
Contains datablock I

CCDC reference: 636169

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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
C20H17NO3Z = 2
Mr = 319.35F(000) = 336
Triclinic, P1Dx = 1.373 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.743 (2) ÅCell parameters from 24 reflections
b = 8.133 (2) Åθ = 4.7–8.9°
c = 13.718 (4) ŵ = 0.09 mm1
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 tubeθmax = 25.0°, θmin = 1.5°
Graphite monochromatorh = 89
ω–2θ scansk = 19
2710 measured reflectionsl = 1516
2707 independent reflections3 standard reflections every 300 reflections
1756 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-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 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.17 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.6942 (2)0.49190 (19)0.58268 (11)0.0412 (6)0.847 (4)
H1o0.69910.48620.52370.062*0.847 (4)
O1'0.9049 (16)0.1770 (11)0.8390 (7)0.060 (4)0.153 (4)
H1'0.94390.25350.80580.090*0.153 (4)
O20.3073 (2)0.4748 (2)0.62411 (11)0.0492 (4)
O30.4867 (2)0.0735 (2)0.85770 (12)0.0615 (5)
N10.3652 (2)0.2179 (2)0.75456 (12)0.0405 (4)
C10.7443 (3)0.3162 (2)0.64635 (13)0.0335 (5)
H10.71310.43740.59900.040*0.153 (4)
C20.6060 (3)0.2191 (2)0.63749 (14)0.0356 (5)
H20.60580.20520.56870.043*
C30.4109 (3)0.3226 (3)0.66743 (14)0.0369 (5)
C40.1945 (3)0.2825 (3)0.81063 (17)0.0528 (6)
H4A0.14900.18330.83700.063*
H4B0.09990.38090.76520.063*
C50.2269 (4)0.3503 (4)0.89678 (18)0.0649 (7)
H5A0.11260.39130.93220.097*
H5B0.26950.45020.87080.097*
H5C0.31920.25260.94240.097*
C60.4997 (3)0.0439 (3)0.78514 (16)0.0424 (5)
C70.6626 (3)0.0308 (3)0.71462 (14)0.0380 (5)
H70.68410.06650.68040.046*
C80.8408 (3)0.0048 (3)0.77496 (14)0.0369 (5)
H80.88110.12410.82450.044*0.847 (4)
C90.9881 (3)0.0115 (3)0.69713 (14)0.0374 (5)
C101.1587 (3)0.1232 (3)0.68973 (16)0.0463 (6)
H101.19260.23790.73520.056*
C111.2786 (3)0.0854 (3)0.61388 (17)0.0518 (6)
H111.39370.17550.60850.062*
C121.2292 (3)0.0841 (3)0.54636 (16)0.0494 (6)
H121.31190.10830.49640.059*
C131.0563 (3)0.2197 (3)0.55214 (15)0.0423 (5)
H131.02180.33330.50550.051*
C140.9371 (3)0.1827 (3)0.62821 (14)0.0355 (5)
C150.7905 (3)0.1526 (2)0.82450 (14)0.0325 (4)
C160.7861 (3)0.1386 (3)0.92730 (14)0.0404 (5)
H160.81820.02440.97330.048*
C170.7335 (3)0.2964 (3)0.96102 (16)0.0482 (6)
H170.73150.28781.03010.058*
C180.6842 (3)0.4655 (3)0.89331 (16)0.0474 (6)
H180.65000.57040.91680.057*
C190.6853 (3)0.4806 (3)0.78976 (15)0.0380 (5)
H190.64980.59520.74400.046*
C200.7395 (3)0.3237 (2)0.75579 (13)0.0321 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0516 (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)
O20.0436 (9)0.0465 (9)0.0454 (9)0.0051 (7)0.0031 (7)0.0076 (7)
O30.0682 (11)0.0554 (10)0.0577 (10)0.0325 (9)0.0044 (8)0.0039 (9)
N10.0378 (10)0.0489 (11)0.0370 (9)0.0185 (9)0.0004 (8)0.0103 (8)
C10.0378 (11)0.0278 (10)0.0296 (10)0.0091 (9)0.0011 (8)0.0031 (8)
C20.0414 (12)0.0360 (11)0.0278 (10)0.0105 (9)0.0017 (8)0.0101 (9)
C30.0401 (12)0.0400 (12)0.0310 (10)0.0125 (10)0.0073 (9)0.0101 (9)
C40.0327 (12)0.0714 (16)0.0536 (14)0.0214 (11)0.0045 (10)0.0126 (12)
C50.0602 (17)0.0843 (19)0.0615 (16)0.0316 (14)0.0181 (13)0.0348 (14)
C60.0498 (14)0.0436 (13)0.0401 (12)0.0243 (11)0.0037 (10)0.0088 (10)
C70.0451 (12)0.0338 (11)0.0374 (11)0.0148 (10)0.0001 (9)0.0116 (9)
C80.0417 (12)0.0280 (10)0.0345 (11)0.0085 (9)0.0001 (9)0.0034 (8)
C90.0390 (12)0.0355 (11)0.0365 (11)0.0091 (9)0.0004 (9)0.0136 (9)
C100.0453 (13)0.0395 (12)0.0456 (12)0.0022 (10)0.0019 (10)0.0152 (10)
C110.0406 (13)0.0582 (15)0.0510 (13)0.0025 (11)0.0038 (11)0.0280 (12)
C120.0414 (13)0.0651 (15)0.0435 (13)0.0164 (11)0.0114 (10)0.0246 (12)
C130.0448 (13)0.0462 (13)0.0371 (11)0.0153 (10)0.0042 (9)0.0155 (10)
C140.0376 (11)0.0364 (11)0.0324 (10)0.0114 (9)0.0030 (9)0.0123 (9)
C150.0281 (10)0.0340 (11)0.0327 (10)0.0090 (8)0.0006 (8)0.0072 (8)
C160.0369 (12)0.0481 (13)0.0336 (11)0.0154 (10)0.0020 (9)0.0057 (10)
C170.0457 (13)0.0683 (16)0.0362 (12)0.0214 (12)0.0045 (10)0.0231 (12)
C180.0434 (13)0.0538 (14)0.0516 (13)0.0149 (11)0.0040 (10)0.0293 (12)
C190.0339 (11)0.0344 (11)0.0454 (12)0.0099 (9)0.0024 (9)0.0137 (9)
C200.0277 (10)0.0346 (11)0.0329 (10)0.0104 (8)0.0028 (8)0.0086 (9)
Geometric parameters (Å, º) top
O1—C11.391 (2)C7—H70.9800
O1—H1o0.8200C8—C91.512 (3)
O1'—C81.371 (7)C8—C151.516 (3)
O1'—H1'0.8200C8—H80.9800
O2—C31.216 (2)C9—C101.382 (3)
O3—C61.209 (2)C9—C141.394 (3)
N1—C31.375 (3)C10—C111.384 (3)
N1—C61.386 (3)C10—H100.9300
N1—C41.461 (3)C11—C121.376 (3)
C1—C201.515 (3)C11—H110.9300
C1—C141.529 (3)C12—C131.393 (3)
C1—C21.578 (3)C12—H120.9300
C1—H10.9800C13—C141.380 (3)
C2—C31.512 (3)C13—H130.9300
C2—C71.540 (3)C15—C161.383 (3)
C2—H20.9800C15—C201.392 (3)
C4—C51.505 (3)C16—C171.386 (3)
C4—H4A0.9700C16—H160.9300
C4—H4B0.9700C17—C181.374 (3)
C5—H5A0.9600C17—H170.9300
C5—H5B0.9600C18—C191.392 (3)
C5—H5C0.9600C18—H180.9300
C6—C71.511 (3)C19—C201.380 (3)
C7—C81.563 (3)C19—H190.9300
C1—O1—H1o109.5O1'—C8—C15115.7 (5)
C8—O1'—H1'109.5C9—C8—C15108.08 (16)
C3—N1—C6112.95 (17)O1'—C8—C7112.1 (5)
C3—N1—C4124.00 (18)C9—C8—C7106.26 (16)
C6—N1—C4123.04 (18)C15—C8—C7105.65 (15)
O1—C1—C20110.22 (15)C9—C8—H8112.1
O1—C1—C14115.17 (16)C15—C8—H8112.1
C20—C1—C14107.35 (15)C7—C8—H8112.1
O1—C1—C2112.55 (16)C10—C9—C14120.15 (19)
C20—C1—C2106.01 (15)C10—C9—C8126.57 (18)
C14—C1—C2104.97 (15)C14—C9—C8113.28 (17)
C20—C1—H1112.7C9—C10—C11119.3 (2)
C14—C1—H1112.7C9—C10—H10120.3
C2—C1—H1112.7C11—C10—H10120.3
C3—C2—C7104.10 (15)C12—C11—C10120.6 (2)
C3—C2—C1111.56 (16)C12—C11—H11119.7
C7—C2—C1109.68 (15)C10—C11—H11119.7
C3—C2—H2110.4C11—C12—C13120.6 (2)
C7—C2—H2110.4C11—C12—H12119.7
C1—C2—H2110.4C13—C12—H12119.7
O2—C3—N1123.64 (19)C14—C13—C12118.9 (2)
O2—C3—C2127.14 (18)C14—C13—H13120.5
N1—C3—C2109.22 (17)C12—C13—H13120.5
N1—C4—C5111.47 (18)C13—C14—C9120.47 (19)
N1—C4—H4A109.3C13—C14—C1125.72 (18)
C5—C4—H4A109.3C9—C14—C1113.81 (17)
N1—C4—H4B109.3C16—C15—C20120.26 (18)
C5—C4—H4B109.3C16—C15—C8126.16 (17)
H4A—C4—H4B108.0C20—C15—C8113.55 (16)
C4—C5—H5A109.5C15—C16—C17119.30 (19)
C4—C5—H5B109.5C15—C16—H16120.4
H5A—C5—H5B109.5C17—C16—H16120.4
C4—C5—H5C109.5C18—C17—C16120.55 (19)
H5A—C5—H5C109.5C18—C17—H17119.7
H5B—C5—H5C109.5C16—C17—H17119.7
O3—C6—N1124.5 (2)C17—C18—C19120.38 (19)
O3—C6—C7127.0 (2)C17—C18—H18119.8
N1—C6—C7108.42 (17)C19—C18—H18119.8
C6—C7—C2105.04 (16)C20—C19—C18119.28 (19)
C6—C7—C8109.92 (16)C20—C19—H19120.4
C2—C7—C8110.08 (15)C18—C19—H19120.4
C6—C7—H7110.6C19—C20—C15120.22 (17)
C2—C7—H7110.6C19—C20—C1125.96 (17)
C8—C7—H7110.6C15—C20—C1113.79 (16)
O1'—C8—C9108.6 (5)
O1—C1—C2—C361.6 (2)C14—C9—C10—C110.6 (3)
C20—C1—C2—C358.93 (19)C8—C9—C10—C11179.6 (2)
C14—C1—C2—C3172.37 (14)C9—C10—C11—C120.0 (3)
O1—C1—C2—C7176.43 (15)C10—C11—C12—C131.0 (3)
C20—C1—C2—C755.87 (19)C11—C12—C13—C141.5 (3)
C14—C1—C2—C757.57 (19)C12—C13—C14—C90.9 (3)
C6—N1—C3—O2175.12 (19)C12—C13—C14—C1179.13 (19)
C4—N1—C3—O25.8 (3)C10—C9—C14—C130.1 (3)
C6—N1—C3—C25.6 (2)C8—C9—C14—C13179.90 (18)
C4—N1—C3—C2173.53 (18)C10—C9—C14—C1179.85 (18)
C7—C2—C3—O2175.98 (19)C8—C9—C14—C10.0 (2)
C1—C2—C3—O265.8 (2)O1—C1—C14—C133.9 (3)
C7—C2—C3—N14.7 (2)C20—C1—C14—C13127.0 (2)
C1—C2—C3—N1113.46 (17)C2—C1—C14—C13120.5 (2)
C3—N1—C4—C596.3 (2)O1—C1—C14—C9176.19 (16)
C6—N1—C4—C582.7 (3)C20—C1—C14—C953.0 (2)
C3—N1—C6—O3177.53 (19)C2—C1—C14—C959.4 (2)
C4—N1—C6—O33.4 (3)O1'—C8—C15—C166.7 (6)
C3—N1—C6—C73.9 (2)C9—C8—C15—C16128.7 (2)
C4—N1—C6—C7175.20 (18)C7—C8—C15—C16117.9 (2)
O3—C6—C7—C2179.2 (2)O1'—C8—C15—C20175.5 (6)
N1—C6—C7—C20.7 (2)C9—C8—C15—C2053.5 (2)
O3—C6—C7—C860.8 (3)C7—C8—C15—C2059.9 (2)
N1—C6—C7—C8117.75 (17)C20—C15—C16—C171.1 (3)
C3—C2—C7—C62.39 (19)C8—C15—C16—C17178.71 (19)
C1—C2—C7—C6117.10 (17)C15—C16—C17—C180.6 (3)
C3—C2—C7—C8120.67 (17)C16—C17—C18—C190.5 (3)
C1—C2—C7—C81.2 (2)C17—C18—C19—C201.2 (3)
C6—C7—C8—O1'69.5 (5)C18—C19—C20—C150.7 (3)
C2—C7—C8—O1'175.2 (5)C18—C19—C20—C1178.54 (19)
C6—C7—C8—C9172.00 (16)C16—C15—C20—C190.4 (3)
C2—C7—C8—C956.76 (19)C8—C15—C20—C19178.31 (17)
C6—C7—C8—C1557.3 (2)C16—C15—C20—C1177.69 (18)
C2—C7—C8—C1557.91 (19)C8—C15—C20—C10.2 (2)
O1'—C8—C9—C100.6 (6)O1—C1—C20—C192.9 (3)
C15—C8—C9—C10126.8 (2)C14—C1—C20—C19129.03 (19)
C7—C8—C9—C10120.2 (2)C2—C1—C20—C19119.2 (2)
O1'—C8—C9—C14179.6 (5)O1—C1—C20—C15179.18 (16)
C15—C8—C9—C1453.4 (2)C14—C1—C20—C1553.0 (2)
C7—C8—C9—C1459.6 (2)C2—C1—C20—C1558.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.821.972.778 (2)169
Symmetry code: (i) x+1, y+1, z+1.
 

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