The incommensurately modulated structure of a tricyclic natural-product-like compound of empirical formula C₂₂H₂₀O₃

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—H...O hydrogen bonds and close-contact approximation.

Computing details

Program(s) used to refine structure: (Jana2000; Petricek and Dusek, 2003); software used to prepare material for publication: (Jana2000; Petricek and Dusek, 2003).

Figures

(I)

Crystal data

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) Å^3	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

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

Refinement on F^2	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0004I^2)
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max = 0.001
wR(F^2) = 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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)