Literature DB >> 21201508

4-(9-Anthryl)-2-methylbutyn-2-ol.

Irena Bylińska¹, Artur Sikorski, Wiesław Wiczk.

Abstract

There are two mol-ecules in the asymmetric unit of the title compound, C(19)H(16)O. Neighbouring mol-ecules are linked through O-H⋯O hydrogen bonds into an R(4) (4)(8) ring motif. There are also C-H⋯π hydrogen and π-π inter-actions. The mol-ecules are either parallel to each other or are inclined at an angle of 12.5 (1)°.

Entities: Chemical Species

Year: 2008 PMID： 21201508 PMCID： PMC2960210 DOI： 10.1107/S1600536808001542

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For applications of this class of compounds, see: Bunz (2000 ▶); De Silva et al. (1999 ▶), Krasovitski & Bolotin (1988 ▶); O’Regan & Grätzel (1991 ▶); Schumm et al. (1994 ▶). For the use of ethynylanthracene derivatives in organic synthesis, see Wen et al. (2004 ▶); Xiao et al. (2007 ▶). For comparison bond dimensions of the anthracene skeleton, see: Cuffet et al. (2005 ▶); Elangovan et al. (2005 ▶). For the structure of 9,10-bis(3-hydroxy-3-methyl-1-butyne)anthracene, see: Dang et al. (2002 ▶).

Experimental

Crystal data

C19H16O M = 260.32 Triclinic, a = 9.995 (2) Å b = 12.738 (3) Å c = 12.905 (3) Å α = 75.70 (3)° β = 72.18 (3)° γ = 68.84 (3)° V = 1441.4 (7) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 298 (2) K 0.60 × 0.20 × 0.10 mm

Data collection

Kuma KM-4 diffractometer Absorption correction: none 5258 measured reflections 5011 independent reflections 2370 reflections with I > 2σ(I) R int = 0.019 3 standard reflections every 200 reflections intensity decay: 1.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.170 S = 0.98 5011 reflections 366 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.34 e Å−3 Data collection: KM-4 Software (Oxford Diffraction, 1995-2003 ▶); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001542/ng2418sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001542/ng2418Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₉H₁₆O	Z = 4
M_r = 260.32	F₀₀₀ = 552
Triclinic, P1	D_x = 1.200 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.995 (2) Å	Cell parameters from 50 reflections
b = 12.738 (3) Å	θ = 2.2–25.0º
c = 12.905 (3) Å	µ = 0.07 mm⁻¹
α = 75.70 (3)º	T = 298 (2) K
β = 72.18 (3)º	Block, white
γ = 68.84 (3)º	0.60 × 0.20 × 0.10 mm
V = 1441.4 (7) Å³

Kuma KM4 diffractometer	R_int = 0.019
Radiation source: fine-focus sealed tube	θ_max = 25.0º
Monochromator: graphite	θ_min = 2.2º
T = 298(2) K	h = −11→11
θ/2θ scans	k = −14→14
Absorption correction: none	l = 0→15
5258 measured reflections	3 standard reflections
5011 independent reflections	every 200 reflections
2370 reflections with I > 2σ(I)	intensity decay: 1.1%

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0961P)² + 0.1391P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.170	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.25 e Å⁻³
5011 reflections	Δρ_min = −0.34 e Å⁻³
366 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (4)
Secondary atom site location: difference Fourier map

Experimental. no

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	U_iso*/U_eq
C1	0.6439 (3)	0.6352 (3)	0.2744 (3)	0.0703 (8)
H1	0.6036	0.6730	0.3353	0.084*
C2	0.7751 (4)	0.6414 (3)	0.2076 (3)	0.0873 (10)
H2	0.8236	0.6839	0.2227	0.105*
C3	0.8389 (4)	0.5848 (3)	0.1160 (3)	0.0878 (11)
H3	0.9293	0.5897	0.0705	0.105*
C4	0.7694 (3)	0.5232 (3)	0.0939 (3)	0.0767 (9)
H4	0.8133	0.4850	0.0333	0.092*
C5	0.5568 (3)	0.4561 (2)	0.1365 (2)	0.0635 (8)
H5	0.6000	0.4182	0.0757	0.076*
C6	0.3395 (4)	0.3939 (3)	0.1734 (3)	0.0737 (9)
H6	0.3822	0.3552	0.1130	0.088*
C7	0.2042 (4)	0.3938 (3)	0.2325 (3)	0.0816 (10)
H7	0.1533	0.3565	0.2125	0.098*
C8	0.1392 (4)	0.4496 (3)	0.3240 (3)	0.0763 (9)
H8	0.0442	0.4507	0.3643	0.092*
C9	0.2129 (3)	0.5021 (2)	0.3547 (2)	0.0626 (8)
H9	0.1693	0.5364	0.4178	0.075*
C10	0.4290 (3)	0.5670 (2)	0.3197 (2)	0.0519 (7)
C11	0.5670 (3)	0.5725 (2)	0.2536 (2)	0.0549 (7)
C12	0.6313 (3)	0.5154 (2)	0.1606 (2)	0.0571 (7)
C13	0.3538 (3)	0.5062 (2)	0.2937 (2)	0.0497 (6)
C14	0.4198 (3)	0.4511 (2)	0.1999 (2)	0.0565 (7)
C15	0.3608 (3)	0.6290 (2)	0.4102 (2)	0.0528 (7)
C16	0.3033 (3)	0.6851 (2)	0.4820 (2)	0.0508 (7)
C17	0.2380 (3)	0.7569 (2)	0.5676 (2)	0.0473 (6)
O18	0.1648 (2)	0.86882 (14)	0.52019 (15)	0.0609 (5)
H18	0.1476	0.9139	0.5618	0.091*
C19	0.1281 (3)	0.7122 (3)	0.6591 (2)	0.0733 (9)
H19A	0.0470	0.7163	0.6316	0.110*
H19B	0.0921	0.7572	0.7173	0.110*
H19C	0.1748	0.6344	0.6869	0.110*
C20	0.3575 (3)	0.7670 (3)	0.6081 (3)	0.0732 (9)
H20A	0.4249	0.7962	0.5474	0.110*
H20B	0.4098	0.6932	0.6413	0.110*
H20C	0.3145	0.8178	0.6618	0.110*
C21	0.8461 (3)	0.1228 (3)	0.0840 (3)	0.0745 (9)
H21	0.8929	0.0796	0.1399	0.089*
C22	0.9110 (4)	0.1911 (3)	0.0040 (3)	0.0928 (11)
H22	1.0007	0.1960	0.0063	0.111*
C23	0.8464 (4)	0.2547 (3)	−0.0822 (3)	0.0838 (10)
H23	0.8933	0.3008	−0.1378	0.101*
C24	0.7175 (4)	0.2495 (2)	−0.0849 (2)	0.0675 (8)
H24	0.6750	0.2926	−0.1429	0.081*
C25	0.5086 (3)	0.1752 (2)	−0.0037 (2)	0.0576 (7)
H25	0.4649	0.2187	−0.0610	0.069*
C26	0.2985 (3)	0.1032 (3)	0.0763 (3)	0.0709 (9)
H26	0.2533	0.1480	0.0201	0.085*
C27	0.2306 (4)	0.0359 (3)	0.1544 (3)	0.0865 (10)
H27	0.1392	0.0347	0.1520	0.104*
C28	0.2958 (4)	−0.0326 (3)	0.2399 (3)	0.0811 (10)
H28	0.2477	−0.0790	0.2940	0.097*
C29	0.4271 (3)	−0.0314 (3)	0.2436 (2)	0.0646 (8)
H29	0.4701	−0.0785	0.3000	0.078*
C30	0.6386 (3)	0.0447 (2)	0.1664 (2)	0.0496 (6)
C31	0.7097 (3)	0.1152 (2)	0.0851 (2)	0.0527 (7)
C32	0.6432 (3)	0.1807 (2)	−0.0028 (2)	0.0533 (7)
C33	0.5030 (3)	0.0397 (2)	0.1639 (2)	0.0509 (7)
C34	0.4362 (3)	0.1077 (2)	0.0770 (2)	0.0547 (7)
C35	0.7051 (3)	−0.0211 (2)	0.2548 (2)	0.0573 (7)
C36	0.7636 (3)	−0.0706 (2)	0.3274 (2)	0.0573 (7)
C37	0.8328 (3)	−0.1305 (2)	0.4196 (2)	0.0559 (7)
O38	0.9388 (2)	−0.07847 (15)	0.41664 (16)	0.0645 (6)
H38	0.9901	−0.1179	0.4596	0.097*
C39	0.9208 (4)	−0.2512 (2)	0.4034 (3)	0.0831 (11)
H39A	0.9937	−0.2516	0.3347	0.125*
H39B	0.8560	−0.2911	0.4026	0.125*
H39C	0.9690	−0.2881	0.4626	0.125*
C40	0.7207 (4)	−0.1233 (3)	0.5257 (3)	0.0870 (11)
H40A	0.6651	−0.0449	0.5313	0.130*
H40B	0.7689	−0.1558	0.5853	0.130*
H40C	0.6552	−0.1644	0.5293	0.130*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.059 (2)	0.082 (2)	0.072 (2)	−0.0160 (16)	−0.0187 (16)	−0.0192 (17)
C2	0.063 (2)	0.114 (3)	0.092 (3)	−0.034 (2)	−0.019 (2)	−0.021 (2)
C3	0.052 (2)	0.127 (3)	0.080 (2)	−0.026 (2)	−0.0044 (18)	−0.023 (2)
C4	0.0560 (19)	0.102 (3)	0.0614 (19)	−0.0108 (17)	−0.0111 (15)	−0.0175 (17)
C5	0.066 (2)	0.0655 (18)	0.0487 (16)	−0.0035 (15)	−0.0127 (14)	−0.0175 (14)
C6	0.091 (3)	0.069 (2)	0.0673 (19)	−0.0273 (18)	−0.0207 (19)	−0.0149 (16)
C7	0.098 (3)	0.081 (2)	0.082 (2)	−0.050 (2)	−0.015 (2)	−0.0135 (19)
C8	0.082 (2)	0.074 (2)	0.075 (2)	−0.0402 (18)	−0.0072 (18)	−0.0058 (18)
C9	0.070 (2)	0.0516 (17)	0.0559 (17)	−0.0165 (14)	−0.0066 (15)	−0.0040 (13)
C10	0.0499 (16)	0.0473 (14)	0.0472 (15)	−0.0010 (12)	−0.0148 (12)	−0.0046 (12)
C11	0.0484 (17)	0.0554 (16)	0.0547 (16)	−0.0031 (13)	−0.0208 (13)	−0.0065 (13)
C12	0.0517 (17)	0.0650 (17)	0.0479 (15)	−0.0064 (13)	−0.0155 (13)	−0.0103 (13)
C13	0.0552 (16)	0.0411 (13)	0.0448 (14)	−0.0081 (12)	−0.0141 (12)	0.0000 (12)
C14	0.0618 (18)	0.0518 (16)	0.0489 (16)	−0.0089 (14)	−0.0169 (14)	−0.0038 (13)
C15	0.0551 (16)	0.0451 (15)	0.0520 (16)	−0.0062 (12)	−0.0163 (13)	−0.0066 (14)
C16	0.0510 (16)	0.0478 (15)	0.0505 (15)	−0.0094 (12)	−0.0146 (13)	−0.0081 (14)
C17	0.0502 (15)	0.0398 (14)	0.0510 (15)	−0.0076 (11)	−0.0191 (12)	−0.0064 (12)
O18	0.0694 (13)	0.0396 (10)	0.0797 (13)	−0.0064 (8)	−0.0369 (10)	−0.0116 (9)
C19	0.078 (2)	0.079 (2)	0.0551 (17)	−0.0200 (17)	−0.0087 (16)	−0.0109 (16)
C20	0.071 (2)	0.0691 (19)	0.091 (2)	−0.0075 (15)	−0.0479 (18)	−0.0183 (17)
C21	0.065 (2)	0.085 (2)	0.077 (2)	−0.0254 (17)	−0.0344 (17)	0.0080 (18)
C22	0.071 (2)	0.111 (3)	0.101 (3)	−0.044 (2)	−0.033 (2)	0.015 (2)
C23	0.080 (2)	0.090 (2)	0.078 (2)	−0.038 (2)	−0.0195 (19)	0.0091 (19)
C24	0.076 (2)	0.0655 (19)	0.0596 (18)	−0.0212 (16)	−0.0258 (16)	0.0034 (15)
C25	0.0621 (19)	0.0519 (16)	0.0553 (16)	−0.0027 (14)	−0.0327 (14)	−0.0013 (13)
C26	0.0574 (19)	0.076 (2)	0.084 (2)	−0.0115 (16)	−0.0340 (17)	−0.0128 (17)
C27	0.0499 (19)	0.112 (3)	0.100 (3)	−0.0241 (19)	−0.0234 (18)	−0.015 (2)
C28	0.066 (2)	0.105 (3)	0.077 (2)	−0.041 (2)	−0.0083 (18)	−0.0102 (19)
C29	0.070 (2)	0.0683 (19)	0.0545 (17)	−0.0186 (15)	−0.0169 (15)	−0.0090 (14)
C30	0.0517 (16)	0.0496 (15)	0.0488 (15)	−0.0073 (12)	−0.0228 (12)	−0.0087 (12)
C31	0.0480 (16)	0.0565 (16)	0.0526 (15)	−0.0089 (13)	−0.0198 (13)	−0.0078 (13)
C32	0.0556 (17)	0.0497 (15)	0.0510 (15)	−0.0077 (13)	−0.0223 (13)	−0.0028 (13)
C33	0.0509 (16)	0.0525 (15)	0.0464 (15)	−0.0076 (12)	−0.0162 (13)	−0.0096 (12)
C34	0.0497 (16)	0.0564 (16)	0.0592 (16)	−0.0061 (13)	−0.0226 (13)	−0.0148 (14)
C35	0.0625 (18)	0.0565 (16)	0.0545 (16)	−0.0120 (13)	−0.0278 (14)	−0.0033 (13)
C36	0.0665 (18)	0.0537 (16)	0.0572 (16)	−0.0168 (13)	−0.0281 (14)	−0.0043 (13)
C37	0.0611 (18)	0.0561 (17)	0.0563 (16)	−0.0114 (13)	−0.0347 (14)	−0.0032 (13)
O38	0.0616 (12)	0.0555 (11)	0.0874 (14)	−0.0091 (9)	−0.0470 (11)	−0.0072 (10)
C39	0.121 (3)	0.0475 (17)	0.088 (2)	−0.0088 (17)	−0.059 (2)	−0.0052 (16)
C40	0.089 (2)	0.103 (3)	0.061 (2)	−0.026 (2)	−0.0264 (18)	0.0053 (18)

C1—C2	1.348 (4)	C21—C22	1.341 (4)
C1—C11	1.407 (4)	C21—C31	1.397 (4)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.397 (5)	C22—C23	1.388 (4)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.343 (5)	C23—C24	1.325 (4)
C3—H3	0.9300	C23—H23	0.9300
C4—C12	1.409 (4)	C24—C32	1.404 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C12	1.373 (4)	C25—C32	1.375 (4)
C5—C14	1.378 (4)	C25—C34	1.375 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.334 (5)	C26—C27	1.336 (5)
C6—C14	1.417 (4)	C26—C34	1.401 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.391 (5)	C27—C28	1.399 (5)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.346 (4)	C28—C29	1.333 (4)
C8—H8	0.9300	C28—H28	0.9300
C9—C13	1.400 (4)	C29—C33	1.419 (4)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.398 (4)	C30—C33	1.390 (4)
C10—C13	1.407 (4)	C30—C31	1.397 (4)
C10—C15	1.426 (4)	C30—C35	1.427 (3)
C11—C12	1.416 (4)	C31—C32	1.421 (3)
C13—C14	1.411 (4)	C33—C34	1.420 (3)
C15—C16	1.185 (4)	C35—C36	1.180 (3)
C16—C17	1.453 (4)	C36—C37	1.466 (3)
C17—O18	1.425 (3)	C37—O38	1.426 (3)
C17—C20	1.498 (4)	C37—C40	1.479 (4)
C17—C19	1.500 (4)	C37—C39	1.500 (4)
O18—H18	0.8200	O38—H38	0.8200
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600

C2—C1—C11	121.2 (3)	C22—C21—C31	121.3 (3)
C2—C1—H1	119.4	C22—C21—H21	119.4
C11—C1—H1	119.4	C31—C21—H21	119.4
C1—C2—C3	120.7 (3)	C21—C22—C23	121.0 (3)
C1—C2—H2	119.7	C21—C22—H22	119.5
C3—C2—H2	119.7	C23—C22—H22	119.5
C4—C3—C2	119.9 (3)	C24—C23—C22	119.7 (3)
C4—C3—H3	120.0	C24—C23—H23	120.1
C2—C3—H3	120.0	C22—C23—H23	120.1
C3—C4—C12	121.4 (3)	C23—C24—C32	122.0 (3)
C3—C4—H4	119.3	C23—C24—H24	119.0
C12—C4—H4	119.3	C32—C24—H24	119.0
C12—C5—C14	121.9 (3)	C32—C25—C34	122.5 (2)
C12—C5—H5	119.1	C32—C25—H25	118.8
C14—C5—H5	119.1	C34—C25—H25	118.8
C7—C6—C14	121.9 (3)	C27—C26—C34	121.5 (3)
C7—C6—H6	119.1	C27—C26—H26	119.2
C14—C6—H6	119.1	C34—C26—H26	119.2
C6—C7—C8	119.9 (3)	C26—C27—C28	120.6 (3)
C6—C7—H7	120.0	C26—C27—H27	119.7
C8—C7—H7	120.0	C28—C27—H27	119.7
C9—C8—C7	120.5 (3)	C29—C28—C27	119.9 (3)
C9—C8—H8	119.7	C29—C28—H28	120.0
C7—C8—H8	119.7	C27—C28—H28	120.0
C8—C9—C13	121.4 (3)	C28—C29—C33	121.9 (3)
C8—C9—H9	119.3	C28—C29—H29	119.1
C13—C9—H9	119.3	C33—C29—H29	119.1
C11—C10—C13	120.4 (2)	C33—C30—C31	121.1 (2)
C11—C10—C15	119.5 (3)	C33—C30—C35	119.7 (3)
C13—C10—C15	120.0 (2)	C31—C30—C35	119.2 (2)
C10—C11—C1	122.4 (3)	C30—C31—C21	123.2 (2)
C10—C11—C12	119.4 (3)	C30—C31—C32	119.1 (2)
C1—C11—C12	118.2 (3)	C21—C31—C32	117.7 (3)
C5—C12—C4	121.9 (3)	C25—C32—C24	122.7 (2)
C5—C12—C11	119.5 (3)	C25—C32—C31	119.0 (3)
C4—C12—C11	118.7 (3)	C24—C32—C31	118.3 (3)
C9—C13—C10	122.5 (3)	C30—C33—C29	123.4 (2)
C9—C13—C14	118.4 (3)	C30—C33—C34	119.1 (2)
C10—C13—C14	119.0 (3)	C29—C33—C34	117.5 (3)
C5—C14—C13	119.8 (3)	C25—C34—C26	122.3 (3)
C5—C14—C6	122.4 (3)	C25—C34—C33	119.2 (2)
C13—C14—C6	117.8 (3)	C26—C34—C33	118.6 (3)
C16—C15—C10	176.9 (3)	C36—C35—C30	176.2 (3)
C15—C16—C17	177.3 (3)	C35—C36—C37	178.5 (3)
O18—C17—C16	108.37 (19)	O38—C37—C36	107.7 (2)
O18—C17—C20	106.5 (2)	O38—C37—C40	110.3 (2)
C16—C17—C20	109.6 (2)	C36—C37—C40	110.7 (2)
O18—C17—C19	109.2 (2)	O38—C37—C39	105.0 (2)
C16—C17—C19	110.9 (2)	C36—C37—C39	110.5 (2)
C20—C17—C19	112.1 (2)	C40—C37—C39	112.4 (3)
C17—O18—H18	109.5	C37—O38—H38	109.5
C17—C19—H19A	109.5	C37—C39—H39A	109.5
C17—C19—H19B	109.5	C37—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C17—C19—H19C	109.5	C37—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
C17—C20—H20A	109.5	C37—C40—H40A	109.5
C17—C20—H20B	109.5	C37—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C17—C20—H20C	109.5	C37—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5

C11—C1—C2—C3	−0.5 (5)	C31—C21—C22—C23	−1.6 (6)
C1—C2—C3—C4	0.0 (6)	C21—C22—C23—C24	1.1 (6)
C2—C3—C4—C12	0.8 (5)	C22—C23—C24—C32	−0.2 (5)
C14—C6—C7—C8	−1.0 (5)	C34—C26—C27—C28	−0.1 (5)
C6—C7—C8—C9	−1.2 (5)	C26—C27—C28—C29	−0.2 (6)
C7—C8—C9—C13	2.5 (5)	C27—C28—C29—C33	1.2 (5)
C13—C10—C11—C1	177.9 (2)	C33—C30—C31—C21	−179.8 (3)
C15—C10—C11—C1	1.6 (4)	C35—C30—C31—C21	1.7 (4)
C13—C10—C11—C12	−0.6 (4)	C33—C30—C31—C32	−1.5 (4)
C15—C10—C11—C12	−176.9 (2)	C35—C30—C31—C32	−179.9 (2)
C2—C1—C11—C10	−178.2 (3)	C22—C21—C31—C30	179.6 (3)
C2—C1—C11—C12	0.3 (4)	C22—C21—C31—C32	1.3 (5)
C14—C5—C12—C4	−178.1 (3)	C34—C25—C32—C24	−179.9 (3)
C14—C5—C12—C11	0.6 (4)	C34—C25—C32—C31	−0.6 (4)
C3—C4—C12—C5	177.6 (3)	C23—C24—C32—C25	179.3 (3)
C3—C4—C12—C11	−1.0 (4)	C23—C24—C32—C31	−0.1 (5)
C10—C11—C12—C5	0.3 (4)	C30—C31—C32—C25	1.8 (4)
C1—C11—C12—C5	−178.2 (3)	C21—C31—C32—C25	−179.8 (3)
C10—C11—C12—C4	179.0 (2)	C30—C31—C32—C24	−178.9 (2)
C1—C11—C12—C4	0.5 (4)	C21—C31—C32—C24	−0.4 (4)
C8—C9—C13—C10	175.6 (3)	C31—C30—C33—C29	179.2 (3)
C8—C9—C13—C14	−1.7 (4)	C35—C30—C33—C29	−2.4 (4)
C11—C10—C13—C9	−177.3 (2)	C31—C30—C33—C34	0.0 (4)
C15—C10—C13—C9	−1.0 (4)	C35—C30—C33—C34	178.4 (2)
C11—C10—C13—C14	0.0 (3)	C28—C29—C33—C30	178.8 (3)
C15—C10—C13—C14	176.3 (2)	C28—C29—C33—C34	−2.0 (4)
C12—C5—C14—C13	−1.2 (4)	C32—C25—C34—C26	179.4 (3)
C12—C5—C14—C6	177.5 (3)	C32—C25—C34—C33	−0.9 (4)
C9—C13—C14—C5	178.3 (2)	C27—C26—C34—C25	179.0 (3)
C10—C13—C14—C5	0.9 (3)	C27—C26—C34—C33	−0.7 (4)
C9—C13—C14—C6	−0.4 (3)	C30—C33—C34—C25	1.2 (4)
C10—C13—C14—C6	−177.8 (2)	C29—C33—C34—C25	−178.0 (3)
C7—C6—C14—C5	−177.0 (3)	C30—C33—C34—C26	−179.1 (3)
C7—C6—C14—C13	1.7 (4)	C29—C33—C34—C26	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O38ⁱ	0.82	2.01	2.726 (3)	145
O38—H38···O18ⁱⁱ	0.82	2.06	2.766 (3)	145

X	H	J	H···J	X···J	X-I···J
C19	H19C	Cg1ⁱⁱⁱ	2.87	3.810 (4)	167
C20	H20B	Cg2ⁱⁱⁱ	2.76	3.703 (4)	168
C24	H24	Cg2^iv	2.64	3.472 (3)	149
C25	H25	Cg1^iv	2.92	3.794 (3)	157

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
3	4^v	3.794 (2)	1.2	3.370 (2)	1.336 (2)
4	3^v	3.794 (2)	1.2	3.404 (2)	1.464 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O38ⁱ	0.82	2.01	2.726 (3)	145
O38—H38⋯O18ⁱⁱ	0.82	2.06	2.766 (3)	145

Symmetry codes: (i) ; (ii) .

Table 2

C—H⋯π interactions (Å,°)

Cg1 is the centroid of the C5/C10–C14 ring and Cg2 is the centroid of the C1–C4/C12/C11 ring.

X	H	J	H⋯J	X⋯J	X—I⋯J
C19	H19C	Cg1ⁱⁱⁱ	2.87	3.810 (4)	167
C20	H20B	Cg2ⁱⁱⁱ	2.76	3.703 (4)	168
C24	H24	Cg2^iv	2.64	3.472 (3)	149
C25	H25	Cg1^iv	2.92	3.794 (3)	157

Symmetry codes: (iii) , , ; (iv) , , .

Table 3

π–π interactions (Å,°)

Cg3 is the centroid of the C25/30–C34 ring and Cg4 is the centroid of the C26-C29/C33/C34 ring. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
3	4^v	3.794 (2)	1.2	3.370 (2)	1.336 (2)
4	3^v	3.794 (2)	1.2	3.404 (2)	1.464 (2)

Symmetry code: (v) , , .

4 in total

4. One step Pd(0)-catalyzed synthesis, X-ray analysis, and photophysical properties of cyclopent[hi]aceanthrylene: fullerene-like properties in a nonalternant cyclopentafused aromatic hydrocarbon.

Authors: Hung Dang; Marcia Levitus; Miguel A Garcia-Garibay
Journal: J Am Chem Soc Date: 2002-01-09 Impact factor: 15.419