research papers
3,4-Diphenyl-2a,5a,6,7,8,8a,8b-heptahydro-furo[4,3,2-de]chromen-2-one (1) was prepared as part of a project aimed at the synthesis of polycyclic natural-product-like scaffolds. X-ray analysis of crystals grown from ethanol revealed an incommensurately modulated structure. Data include main and satellite reflections up to second order. The modulation vector was refined using the NADA program. The modulated character of the structure of the organic compound C22H20O3 is interpreted in terms of the intermolecular C—HO hydrogen bonds and close-contact approximation.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810600930X/og5016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810600930X/og5016sup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010876810600930X/og5016sup3.pdf |
Computing details top
Program(s) used to refine structure: (Jana2000; Petricek and Dusek, 2003); software used to prepare material for publication: (Jana2000; Petricek and Dusek, 2003).
(I) top
Crystal data top
3·4−−diphenyl−2a·5a·6·7·8·8a·8b−heptahydro−furo[4·3·2−−de]chromen−2−−one | F(000) = 704 |
Mr = 332.4 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/c(α0γ)00† | Mo Kα radiation, λ = 0.71069 Å |
q = 0.25290a* + -1.21270c* | Cell parameters from 6774 reflections |
a = 7.2527 (9) Å | θ = 1.6–25.6° |
b = 24.951 (3) Å | µ = 0.09 mm−1 |
c = 9.8959 (10) Å | T = 173 K |
β = 106.645 (8)° | Rod, colourless |
V = 1715.8 (4) Å3 | 0.50 × 0.22 × 0.20 mm |
Z = 4 |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, 1/2+x2, 1/2−x3, −x4; (3) −x1, −x2, −x3, −x4; (4) x1, 1/2−x2, 1/2+x3, x4. |
Data collection top
Stoe IPDS-II diffractometer | Rint = 0.038 |
ω scans | θmax = 51.6°, θmin = 1.7° |
12976 measured reflections | h = −8→8 |
40786 independent reflections | k = −29→29 |
12976 reflections with I > 3σ(I) | l = −11→11 |
Refinement top
Refinement on F2 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max = 0.001 |
wR(F2) = 0.087 | Δρmax = 0.13 e Å−3 |
S = 0.79 | Δρmin = −0.14 e Å−3 |
40786 reflections | Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974) |
328 parameters | Extinction coefficient: 0.78 (3) |
Crystal data top
3·4−−diphenyl−2a·5a·6·7·8·8a·8b−heptahydro−furo[4·3·2−−de]chromen−2−−one | β = 106.645 (8)° |
Mr = 332.4 | V = 1715.8 (4) Å3 |
Monoclinic, P21/c(α0γ)00† | Z = 4 |
q = 0.25290a* + -1.21270c* | Mo Kα radiation |
a = 7.2527 (9) Å | µ = 0.09 mm−1 |
b = 24.951 (3) Å | T = 173 K |
c = 9.8959 (10) Å | 0.50 × 0.22 × 0.20 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, 1/2+x2, 1/2−x3, −x4; (3) −x1, −x2, −x3, −x4; (4) x1, 1/2−x2, 1/2+x3, x4. |
Data collection top
Stoe IPDS-II diffractometer | 12976 reflections with I > 3σ(I) |
12976 measured reflections | Rint = 0.038 |
40786 independent reflections |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 328 parameters |
wR(F2) = 0.087 | Δρmax = 0.13 e Å−3 |
S = 0.79 | Δρmin = −0.14 e Å−3 |
40786 reflections |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1a | 0.06084 (10) | 0.33361 (3) | 0.34172 (7) | 0.0259 (3) | |
C2a | 0.21027 (16) | 0.33613 (5) | 0.45965 (11) | 0.0260 (3) | |
C3a | 0.30375 (16) | 0.28319 (5) | 0.50984 (11) | 0.0279 (2) | |
C4a | 0.16577 (16) | 0.23669 (5) | 0.50928 (11) | 0.0278 (2) | |
C5a | −0.03064 (16) | 0.24806 (5) | 0.40510 (11) | 0.0286 (3) | |
C6a | −0.13838 (17) | 0.19954 (5) | 0.33403 (12) | 0.0347 (3) | |
C7a | −0.01272 (16) | 0.16259 (5) | 0.27641 (12) | 0.0328 (3) | |
C8a | 0.15514 (17) | 0.14294 (5) | 0.39616 (12) | 0.0348 (3) | |
C9a | 0.27408 (17) | 0.18820 (5) | 0.47561 (12) | 0.0317 (3) | |
C10a | 0.41384 (17) | 0.26273 (5) | 0.41007 (12) | 0.0325 (3) | |
O1a | −0.01032 (15) | 0.28351 (4) | 0.29260 (10) | 0.02760 (18) | |
O2a | 0.39139 (15) | 0.20991 (5) | 0.39030 (10) | 0.0349 (2) | |
O3a | 0.50849 (15) | 0.28898 (5) | 0.35168 (11) | 0.0445 (2) | |
H3a | 0.38031 (10) | 0.29203 (3) | 0.60479 (7) | 0.0335* | |
H4a | 0.13395 (10) | 0.23071 (3) | 0.59684 (7) | 0.0334* | |
H5a | −0.10597 (10) | 0.26494 (3) | 0.45998 (7) | 0.0343* | |
H61a | −0.18874 (10) | 0.18003 (3) | 0.40051 (7) | 0.0416* | |
H62a | −0.24859 (10) | 0.21078 (3) | 0.25782 (7) | 0.0416* | |
H71a | −0.08821 (10) | 0.13218 (3) | 0.23027 (7) | 0.0394* | |
H72a | 0.03559 (10) | 0.18190 (3) | 0.20854 (7) | 0.0394* | |
H81a | 0.10721 (10) | 0.12142 (3) | 0.46047 (7) | 0.0418* | |
H82a | 0.23570 (10) | 0.11957 (3) | 0.35888 (7) | 0.0418* | |
H9a | 0.34744 (10) | 0.17155 (3) | 0.56308 (7) | 0.038* | |
C17a | −0.03780 (11) | 0.37696 (3) | 0.24786 (6) | 0.0264 (3) | |
C18a | 0.06127 (19) | 0.42215 (5) | 0.22494 (11) | 0.0314 (3) | |
C19a | −0.0330 (2) | 0.46210 (5) | 0.13544 (12) | 0.0372 (4) | |
C20a | −0.2258 (2) | 0.45736 (5) | 0.06497 (12) | 0.0407 (4) | |
C21a | −0.3240 (2) | 0.41270 (5) | 0.08547 (13) | 0.0457 (4) | |
C22a | −0.23196 (18) | 0.37255 (5) | 0.17630 (12) | 0.0370 (3) | |
H18a | 0.19775 (11) | 0.42584 (3) | 0.27194 (6) | 0.0377* | |
H19a | 0.03701 (11) | 0.49383 (3) | 0.12194 (6) | 0.0446* | |
H20a | −0.29208 (11) | 0.48531 (3) | 0.00129 (6) | 0.0489* | |
H21a | −0.45967 (11) | 0.40947 (3) | 0.03534 (6) | 0.0548* | |
H22a | −0.30379 (11) | 0.34121 (3) | 0.18986 (6) | 0.0444* | |
C11a | 0.29006 (11) | 0.38616 (3) | 0.53273 (7) | 0.0286 (3) | |
C12a | 0.48727 (19) | 0.39440 (5) | 0.57860 (12) | 0.0412 (4) | |
C13a | 0.5623 (2) | 0.44154 (6) | 0.64588 (13) | 0.0532 (4) | |
C14a | 0.4430 (2) | 0.48101 (5) | 0.66968 (13) | 0.0500 (5) | |
C15a | 0.2468 (2) | 0.47306 (5) | 0.62624 (12) | 0.0402 (4) | |
C16a | 0.1712 (2) | 0.42601 (5) | 0.55957 (12) | 0.0328 (3) | |
H12a | 0.57370 (11) | 0.36688 (3) | 0.56346 (7) | 0.0495* | |
H13a | 0.70050 (11) | 0.44700 (3) | 0.67679 (7) | 0.0639* | |
H14a | 0.49653 (11) | 0.51402 (3) | 0.71652 (7) | 0.06* | |
H15a | 0.16167 (11) | 0.50070 (3) | 0.64264 (7) | 0.0483* | |
H16a | 0.03286 (11) | 0.42089 (3) | 0.53124 (7) | 0.0393* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1a | 0.0254 (4) | 0.0259 (5) | 0.0281 (4) | −0.0009 (4) | 0.0103 (3) | −0.0030 (3) |
C2a | 0.0243 (4) | 0.0296 (5) | 0.0243 (4) | 0.0006 (4) | 0.0075 (3) | −0.0012 (3) |
C3a | 0.0269 (4) | 0.0332 (5) | 0.0220 (3) | 0.0025 (4) | 0.0044 (3) | −0.0031 (3) |
C4a | 0.0306 (4) | 0.0318 (4) | 0.0233 (3) | 0.0013 (4) | 0.0112 (3) | 0.0014 (3) |
C5a | 0.0282 (4) | 0.0323 (5) | 0.0291 (3) | 0.0002 (3) | 0.0142 (3) | 0.0021 (3) |
C6a | 0.0288 (4) | 0.0335 (5) | 0.0420 (4) | −0.0030 (4) | 0.0107 (4) | 0.0035 (4) |
C7a | 0.0316 (4) | 0.0324 (5) | 0.0334 (4) | −0.0037 (4) | 0.0075 (3) | −0.0028 (4) |
C8a | 0.0379 (5) | 0.0319 (5) | 0.0349 (4) | 0.0016 (4) | 0.0108 (4) | −0.0004 (4) |
C9a | 0.0335 (4) | 0.0336 (5) | 0.0269 (4) | 0.0039 (4) | 0.0070 (3) | 0.0043 (3) |
C10a | 0.0217 (4) | 0.0392 (6) | 0.0335 (4) | 0.0062 (4) | 0.0030 (3) | 0.0021 (4) |
O1a | 0.0287 (3) | 0.0279 (3) | 0.0250 (2) | −0.0003 (2) | 0.0057 (2) | 0.0009 (2) |
O2a | 0.0293 (3) | 0.0351 (4) | 0.0434 (3) | 0.0029 (3) | 0.0156 (2) | −0.0049 (3) |
O3a | 0.0337 (3) | 0.0492 (5) | 0.0573 (3) | 0.0016 (3) | 0.0238 (3) | 0.0041 (3) |
C17a | 0.0285 (5) | 0.0305 (5) | 0.0203 (4) | 0.0016 (4) | 0.0073 (4) | −0.0014 (3) |
C18a | 0.0276 (6) | 0.0433 (6) | 0.0229 (4) | −0.0017 (5) | 0.0064 (4) | 0.0001 (4) |
C19a | 0.0441 (7) | 0.0391 (6) | 0.0278 (5) | −0.0049 (5) | 0.0094 (5) | 0.0050 (4) |
C20a | 0.0445 (8) | 0.0407 (6) | 0.0314 (5) | 0.0058 (5) | 0.0020 (5) | 0.0085 (4) |
C21a | 0.0340 (6) | 0.0426 (6) | 0.0494 (6) | −0.0006 (5) | −0.0057 (5) | 0.0085 (5) |
C22a | 0.0309 (5) | 0.0335 (5) | 0.0403 (5) | −0.0028 (4) | 0.0004 (4) | 0.0048 (4) |
C11a | 0.0291 (5) | 0.0325 (5) | 0.0220 (4) | 0.0038 (4) | 0.0041 (4) | 0.0019 (3) |
C12a | 0.0315 (6) | 0.0365 (6) | 0.0475 (5) | 0.0042 (4) | −0.0018 (4) | −0.0082 (4) |
C13a | 0.0334 (7) | 0.0456 (6) | 0.0691 (7) | −0.0005 (5) | −0.0038 (6) | −0.0141 (5) |
C14a | 0.0536 (9) | 0.0394 (6) | 0.0477 (6) | 0.0018 (6) | −0.0003 (6) | −0.0099 (5) |
C15a | 0.0494 (8) | 0.0371 (6) | 0.0335 (5) | 0.0106 (5) | 0.0110 (6) | −0.0020 (4) |
C16a | 0.0329 (6) | 0.0378 (5) | 0.0270 (4) | 0.0021 (5) | 0.0076 (4) | −0.000055 (16) |
Experimental details
Crystal data | |
Chemical formula | 3·4−−diphenyl−2a·5a·6·7·8·8a·8b−heptahydro−furo[4·3·2−−de]chromen−2−−one |
Mr | 332.4 |
Crystal system, space group | Monoclinic, P21/c(α0γ)00† |
Temperature (K) | 173 |
Wave vectors | q = 0.25290a* + -1.21270c* |
a, b, c (Å) | 7.2527 (9), 24.951 (3), 9.8959 (10) |
β (°) | 106.645 (8) |
V (Å3) | 1715.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDS-II diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 3σ(I)] reflections | 12976, 40786, 12976 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 1.102 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.087, 0.79 |
No. of reflections | 40786 |
No. of parameters | 328 |
No. of restraints | ? |
Δρmax, Δρmin (e Å−3) | 0.13, −0.14 |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1, 1/2+x2, 1/2−x3, −x4; (3) −x1, −x2, −x3, −x4; (4) x1, 1/2−x2, 1/2+x3, x4.
Computer programs: (Jana2000; Petricek and Dusek, 2003).