6,7-Dihydrodibenzo[e,g]azulen-8(5H)-one and 12,13-dihydrobenzo[e]­napth­[2,1-g]­azulen-14(11H)-one

In the structures of the title compounds, 6,7-di­hydro­dibenzo[e,g]­azulen-8(5H)-one, C₁₈H₁₄O, (I), and 12,13-di­hydro­benzo[e]­napth­[2,1-g]­azulen-14(11H)-one, C₂₂H₁₆O, (II), the azulene group is in a boat-envelope conformation. The structures are stabilized by weak C—H...O interactions.

S1. Comment

Both the title compounds, (I) and (II), possess an azulene skeleton similar to that found in the natural products extracted from Saussurea lappa, a well known medicinal plant used in the indigenous system of medicine in India for the treatment of coughs, asthma, fever, dyspepsia and leprosy, and as a diuretic and anthelmintic. They are also extensively used in China, as powerful stimulants, carminatives and antispasmodics (Salooja et al., 1950; Kalsi et al., 1983). \sch

The structures of the two molecules are shown in Figs. 1 and 2, for (I) and (II), respectively. Selected bond lengths and angles are given in Tables 1 and 3, and the dimensions of possible hydrogen bonds are in Tables 2 and 4, for (I) and (II), respectively. Query revised text to go here. In both molecules, the cycloheptane rings are in the boat conformation and the cyclopentane rings are in the envelope conformation. The puckering parameters evaluated using PARST (Nardelli, 1995) also confirm the above results. For the seven-membered rings in (I), q₂ = 0.527 (1), q₃ = 0.082 (2) and Q_T = 0.534 (1) Å, and ϕ₂ = 179.73 (15) and ϕ₃ = 148.7 (10)°, while in (II), q₂ = 0.652 (1), q₃ = 0.149 (1) and Q_T = 0.669 (1) Å, and ϕ₂ = 171.60 (12) and ϕ₃ = −166.7 (5)°. For the five-membered rings in (I), q₂ = 0.261 (2) Å and ϕ₂ = −142.3 (4)°, while in (II), q₂ = 0.280 (2) Å and ϕ₂ = 38.6 (3)°. The superposition of the non-H atoms in the common parts of the two molecules (Fig. 3) shows that they have practically the same geometry with an r.m.s. deviation of 0.19 Å (the r.m.s. deviation is 0.08 Å when the atoms in the azulene rings alone are superimposed).

From the nature of the molecules in the two compounds it is clear that strong intermolecular hydrogen bonds are not possible, and in such cases C—H···O bonds play an important role in crystal packing (Desiraju, 1991, 1996). The significant shortening of some of the C—C bonds in the molecules [e.g. C9—C10 and C10—C11 in (I), and C3—C4 and C5—C6 in (II)] probably facilitates activation of the adjacent Csp² atoms to act as donors. In both (I) and (II), the molecules are packed in columns parallel to the c axis. In (I) (Fig. 4), the adjacent columns are interlinked through C—H···O interactions. However, in (II) (Fig. 5), C—H···O interactions are confined to molecules within the columns and the columns are held together purely by van der Waals interactions.

S2. Experimental

Compounds (I) and (II) were prepared by rearranging the vinyl carbinol with two equivalents of potassium hydride in refluxing tetrahydrofuran (Geetha et al., 1982). Crystals suitable for X-ray diffraction studies were grown by slow evaporation from hexane solution.

S3. Refinement

Please provide details of H-atom refinement.

Computing details

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids. H atoms are omitted for clarity.
	Fig. 2. The molecular structure of (II) with 30% probability displacement ellipsoids. H atoms are omitted for clarity.
	Fig. 3. Superposition of the non-H atoms of the two molecules. The black line indicates compound (I), the grey line compound (II).
	Fig. 4. The packing diagram for (I) viewed along the a axis.
	Fig. 5. The packing diagram for (II) viewed along the a axis.

(I) 6,7-Dihydrodibenz[e,g]azulen-8(5H)-one

Crystal data

C18H14O	Dx = 1.304 Mg m^−3
Mr = 246.29	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
a = 8.0547 (11) Å	θ = 14–25°
b = 17.378 (2) Å	µ = 0.62 mm^−1
c = 17.919 (3) Å	T = 273 K
V = 2508.2 (6) Å^3	Rectangular prism, colourless
Z = 8	0.40 × 0.18 × 0.05 mm
F(000) = 1040

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 77.7°, θmin = 4.9°
Graphite monochromator	h = 0→9
ω/2θ scans	k = 0→22
2449 measured reflections	l = −21→0
2449 independent reflections	3 standard reflections every 120min min
1794 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.2676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2449 reflections	Δρmax = 0.18 e Å^−3
229 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (3)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.90909 (15)	0.25092 (6)	0.32332 (6)	0.0565 (3)
C1	0.8925 (2)	−0.04182 (8)	0.42316 (10)	0.0509 (4)
C2	0.9632 (2)	−0.10516 (9)	0.39218 (12)	0.0623 (5)
C3	0.9781 (3)	−0.11203 (9)	0.31377 (12)	0.0680 (5)
C4	0.9271 (2)	−0.05389 (9)	0.26744 (10)	0.0578 (5)
C5	0.8143 (2)	0.05596 (9)	0.15673 (8)	0.0466 (4)
C6	0.7570 (2)	0.12968 (10)	0.12137 (9)	0.0513 (4)
C7	0.8143 (2)	0.18930 (9)	0.17847 (9)	0.0469 (4)
C8	0.84742 (17)	0.18801 (7)	0.32500 (8)	0.0396 (3)
C9	0.7133 (2)	0.21353 (9)	0.44720 (9)	0.0502 (4)
C10	0.6273 (2)	0.19585 (11)	0.51310 (10)	0.0593 (5)
C11	0.6032 (2)	0.12177 (12)	0.53156 (9)	0.0594 (5)
C12	0.6699 (2)	0.06669 (10)	0.48556 (8)	0.0508 (4)
C13	0.76031 (18)	0.08236 (7)	0.41822 (7)	0.0390 (3)
C14	0.77629 (17)	0.15843 (8)	0.39808 (8)	0.0389 (3)
C15	0.82399 (17)	0.14700 (7)	0.25322 (8)	0.0382 (3)
C16	0.82588 (17)	0.07240 (7)	0.24188 (7)	0.0381 (3)
C17	0.86120 (18)	0.01293 (7)	0.29717 (8)	0.0417 (3)
C18	0.83856 (17)	0.01847 (7)	0.37777 (8)	0.0404 (3)
H1	0.880 (2)	−0.0366 (8)	0.4787 (9)	0.050 (4)*
H2	1.002 (2)	−0.1453 (10)	0.4290 (10)	0.070 (5)*
H3	1.023 (2)	−0.1582 (11)	0.2890 (10)	0.080 (6)*
H4	0.938 (2)	−0.0582 (10)	0.2116 (10)	0.073 (6)*
H51	0.738 (2)	0.0144 (10)	0.1439 (10)	0.060 (5)*
H52	0.931 (2)	0.0401 (9)	0.1339 (10)	0.065 (5)*
H61	0.802 (2)	0.1390 (9)	0.0659 (10)	0.064 (5)*
H62	0.630 (3)	0.1313 (10)	0.1183 (11)	0.073 (6)*
H71	0.737 (2)	0.2313 (11)	0.1821 (9)	0.066 (6)*
H72	0.929 (2)	0.2107 (10)	0.1663 (9)	0.063 (5)*
H9	0.727 (2)	0.2652 (10)	0.4312 (8)	0.054 (5)*
H10	0.579 (2)	0.2367 (11)	0.5481 (10)	0.077 (6)*
H11	0.540 (3)	0.1060 (10)	0.5790 (10)	0.074 (6)*
H12	0.653 (2)	0.0137 (10)	0.5005 (9)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0731 (8)	0.0347 (5)	0.0618 (7)	−0.0131 (5)	−0.0059 (6)	−0.0001 (5)
C1	0.0560 (9)	0.0384 (7)	0.0582 (10)	−0.0082 (7)	−0.0107 (8)	0.0090 (7)
C2	0.0677 (11)	0.0337 (8)	0.0855 (13)	−0.0019 (7)	−0.0159 (10)	0.0103 (8)
C3	0.0803 (13)	0.0337 (7)	0.0899 (14)	0.0080 (8)	−0.0078 (11)	−0.0060 (8)
C4	0.0727 (12)	0.0373 (7)	0.0635 (11)	0.0062 (8)	−0.0014 (9)	−0.0085 (7)
C5	0.0518 (9)	0.0472 (8)	0.0408 (8)	−0.0032 (7)	0.0043 (7)	−0.0069 (6)
C6	0.0586 (10)	0.0577 (9)	0.0377 (8)	0.0007 (8)	0.0000 (8)	0.0015 (7)
C7	0.0517 (9)	0.0438 (8)	0.0452 (8)	−0.0026 (7)	0.0008 (7)	0.0055 (6)
C8	0.0406 (8)	0.0320 (6)	0.0463 (8)	0.0005 (6)	−0.0054 (6)	−0.0007 (5)
C9	0.0511 (9)	0.0493 (9)	0.0501 (9)	0.0073 (7)	−0.0056 (7)	−0.0092 (7)
C10	0.0552 (10)	0.0747 (11)	0.0481 (9)	0.0115 (9)	0.0003 (8)	−0.0145 (8)
C11	0.0543 (10)	0.0842 (13)	0.0397 (9)	0.0017 (9)	0.0050 (7)	0.0008 (8)
C12	0.0510 (9)	0.0595 (9)	0.0418 (8)	−0.0068 (8)	−0.0005 (7)	0.0056 (7)
C13	0.0372 (7)	0.0413 (7)	0.0385 (7)	−0.0044 (6)	−0.0050 (6)	0.0010 (6)
C14	0.0378 (7)	0.0388 (7)	0.0402 (7)	0.0007 (5)	−0.0050 (6)	−0.0027 (5)
C15	0.0358 (7)	0.0378 (6)	0.0411 (7)	−0.0019 (5)	0.0015 (6)	0.0011 (6)
C16	0.0360 (7)	0.0388 (6)	0.0396 (7)	−0.0026 (5)	0.0027 (6)	−0.0021 (6)
C17	0.0439 (8)	0.0320 (6)	0.0491 (8)	−0.0036 (6)	−0.0030 (6)	−0.0031 (6)
C18	0.0408 (7)	0.0325 (6)	0.0480 (8)	−0.0057 (6)	−0.0044 (6)	0.0013 (6)

Geometric parameters (Å, º)

O1—C8	1.2011 (16)	C7—H71	0.961 (19)
C1—C2	1.358 (2)	C7—H72	1.023 (18)
C1—C18	1.3959 (19)	C8—C15	1.4825 (19)
C1—H1	1.004 (16)	C8—C14	1.5191 (19)
C2—C3	1.415 (3)	C9—C14	1.3958 (19)
C2—H2	1.011 (18)	C9—C10	1.403 (2)
C3—C4	1.370 (2)	C9—H9	0.949 (16)
C3—H3	0.985 (19)	C10—C11	1.343 (3)
C4—C17	1.384 (2)	C10—H10	1.025 (19)
C4—H4	1.008 (18)	C11—C12	1.373 (2)
C5—C6	1.502 (2)	C11—H11	1.03 (2)
C5—C16	1.555 (2)	C12—C13	1.435 (2)
C5—H51	0.973 (18)	C12—H12	0.968 (17)
C5—H52	1.063 (18)	C13—C14	1.3765 (18)
C6—C7	1.527 (2)	C13—C18	1.4681 (19)
C6—H61	1.070 (17)	C15—C16	1.3123 (18)
C6—H62	1.02 (2)	C16—C17	1.4596 (19)
C7—C15	1.530 (2)	C17—C18	1.459 (2)
C2—C1—C18	120.05 (16)	C15—C8—C14	122.50 (12)
C2—C1—H1	121.3 (9)	C14—C9—C10	124.05 (16)
C18—C1—H1	118.6 (9)	C14—C9—H9	114.6 (10)
C1—C2—C3	120.65 (16)	C10—C9—H9	121.3 (10)
C1—C2—H2	115.1 (10)	C11—C10—C9	119.23 (16)
C3—C2—H2	124.3 (10)	C11—C10—H10	117.2 (10)
C4—C3—C2	120.92 (16)	C9—C10—H10	123.5 (11)
C4—C3—H3	115.9 (11)	C10—C11—C12	117.63 (16)
C2—C3—H3	123.2 (11)	C10—C11—H11	122.0 (10)
C3—C4—C17	120.03 (17)	C12—C11—H11	120.3 (11)
C3—C4—H4	121.5 (11)	C11—C12—C13	124.84 (16)
C17—C4—H4	118.5 (11)	C11—C12—H12	116.3 (10)
C6—C5—C16	106.01 (12)	C13—C12—H12	118.9 (10)
C6—C5—H51	109.9 (10)	C14—C13—C12	116.74 (13)
C16—C5—H51	114.0 (10)	C14—C13—C18	123.83 (13)
C6—C5—H52	109.3 (9)	C12—C13—C18	119.31 (12)
C16—C5—H52	111.8 (10)	C13—C14—C9	117.35 (14)
H51—C5—H52	105.9 (13)	C13—C14—C8	125.89 (12)
C5—C6—C7	101.73 (13)	C9—C14—C8	116.65 (13)
C5—C6—H61	114.7 (9)	C16—C15—C8	127.43 (13)
C7—C6—H61	114.7 (9)	C16—C15—C7	109.86 (13)
C5—C6—H62	110.7 (11)	C8—C15—C7	122.35 (11)
C7—C6—H62	108.6 (11)	C15—C16—C17	126.62 (13)
H61—C6—H62	106.4 (15)	C15—C16—C5	109.43 (12)
C6—C7—C15	106.02 (12)	C17—C16—C5	123.21 (12)
C6—C7—H71	111.4 (11)	C4—C17—C18	118.98 (13)
C15—C7—H71	109.8 (10)	C4—C17—C16	114.06 (14)
C6—C7—H72	112.2 (10)	C18—C17—C16	126.94 (12)
C15—C7—H72	108.3 (9)	C1—C18—C17	119.24 (13)
H71—C7—H72	109.0 (14)	C1—C18—C13	114.44 (14)
O1—C8—C15	117.94 (13)	C17—C18—C13	126.32 (12)
O1—C8—C14	119.04 (13)
C18—C1—C2—C3	−2.1 (3)	C6—C7—C15—C16	17.09 (18)
C1—C2—C3—C4	2.4 (3)	C6—C7—C15—C8	−169.36 (14)
C2—C3—C4—C17	0.5 (3)	C8—C15—C16—C17	−3.8 (2)
C16—C5—C6—C7	24.55 (17)	C7—C15—C16—C17	169.33 (14)
C5—C6—C7—C15	−25.26 (17)	C8—C15—C16—C5	−174.15 (14)
C14—C9—C10—C11	0.4 (3)	C7—C15—C16—C5	−1.01 (17)
C9—C10—C11—C12	2.2 (3)	C6—C5—C16—C15	−15.70 (18)
C10—C11—C12—C13	−1.6 (3)	C6—C5—C16—C17	173.56 (14)
C11—C12—C13—C14	−1.8 (2)	C3—C4—C17—C18	−3.4 (3)
C11—C12—C13—C18	174.35 (16)	C3—C4—C17—C16	174.89 (16)
C12—C13—C14—C9	4.2 (2)	C15—C16—C17—C4	−152.49 (15)
C18—C13—C14—C9	−171.75 (14)	C5—C16—C17—C4	16.6 (2)
C12—C13—C14—C8	−172.02 (13)	C15—C16—C17—C18	25.6 (2)
C18—C13—C14—C8	12.0 (2)	C5—C16—C17—C18	−165.26 (14)
C10—C9—C14—C13	−3.8 (2)	C2—C1—C18—C17	−0.9 (2)
C10—C9—C14—C8	172.81 (15)	C2—C1—C18—C13	178.35 (14)
O1—C8—C14—C13	−153.67 (14)	C4—C17—C18—C1	3.6 (2)
C15—C8—C14—C13	34.8 (2)	C16—C17—C18—C1	−174.42 (14)
O1—C8—C14—C9	30.1 (2)	C4—C17—C18—C13	−175.48 (15)
C15—C8—C14—C9	−141.46 (14)	C16—C17—C18—C13	6.5 (2)
O1—C8—C15—C16	149.69 (16)	C14—C13—C18—C1	144.32 (14)
C14—C8—C15—C16	−38.7 (2)	C12—C13—C18—C1	−31.53 (19)
O1—C8—C15—C7	−22.7 (2)	C14—C13—C18—C17	−36.5 (2)
C14—C8—C15—C7	148.98 (14)	C12—C13—C18—C17	147.61 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.949 (16)	2.438 (16)	2.799 (2)	102.3 (12)
C3—H3···O1^i	0.985 (19)	2.616 (19)	3.540 (2)	156.3 (15)
C6—H62···O1^ii	1.02 (2)	2.930 (19)	3.643 (2)	127.4 (13)
C7—H71···O1^ii	0.961 (19)	2.66 (2)	3.435 (2)	137.4 (14)
C10—H10···O1^iii	1.025 (19)	2.687 (19)	3.541 (2)	140.8 (14)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2; (iii) x−1/2, −y+1/2, −z+1.

(II) 12,13-Dihydrobenzo[e]napth[2,1-g]azulen-14(11H)-one

Crystal data

C22H16O	Dx = 1.285 Mg m^−3
Mr = 296.35	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
a = 11.8466 (12) Å	θ = 14–24°
b = 12.4890 (15) Å	µ = 0.60 mm^−1
c = 20.703 (2) Å	T = 293 K
V = 3063.0 (6) Å^3	Rectangular prism, colourless
Z = 8	0.15 × 0.08 × 0.05 mm
F(000) = 1248

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 70.9°, θmin = 4.3°
Graphite monochromator	h = 0→14
ω/2θ scans	k = 0→15
2949 measured reflections	l = 0→25
2948 independent reflections	3 standard reflections every 120min min
2160 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.2784P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2948 reflections	Δρmax = 0.19 e Å^−3
273 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (3)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	−0.12969 (9)	0.21905 (11)	0.38557 (5)	0.0606 (3)
C1	−0.00641 (14)	0.06816 (13)	0.30270 (7)	0.0490 (4)
C2	0.00515 (16)	−0.00963 (14)	0.25635 (8)	0.0581 (4)
C3	0.09235 (16)	−0.00323 (15)	0.21051 (8)	0.0597 (4)
C4	0.16637 (15)	0.07951 (15)	0.21238 (7)	0.0558 (4)
C5	0.23758 (13)	0.24400 (14)	0.26468 (7)	0.0527 (4)
C6	0.23157 (13)	0.31764 (14)	0.31247 (7)	0.0491 (4)
C7	0.18932 (14)	0.50241 (13)	0.39126 (8)	0.0546 (4)
C8	0.20884 (16)	0.58344 (14)	0.43469 (10)	0.0626 (5)
C9	0.18950 (14)	0.56651 (13)	0.49943 (9)	0.0586 (4)
C10	0.14778 (13)	0.46942 (13)	0.51957 (8)	0.0499 (4)
C11	0.07039 (15)	0.26395 (15)	0.57363 (7)	0.0515 (4)
C12	0.01631 (17)	0.15303 (16)	0.57657 (8)	0.0616 (5)
C13	−0.05923 (15)	0.14783 (14)	0.51674 (8)	0.0526 (4)
C14	−0.03145 (11)	0.22950 (11)	0.40309 (7)	0.0411 (3)
C15	−0.00086 (11)	0.22363 (11)	0.47119 (6)	0.0395 (3)
C16	0.07015 (11)	0.29004 (11)	0.50229 (6)	0.0395 (3)
C17	0.12362 (11)	0.38606 (11)	0.47623 (7)	0.0400 (3)
C18	0.14892 (11)	0.40165 (11)	0.40997 (7)	0.0411 (3)
C19	0.14428 (11)	0.31635 (11)	0.36015 (6)	0.0397 (3)
C20	0.06275 (11)	0.23692 (11)	0.35559 (6)	0.0382 (3)
C21	0.06867 (11)	0.15600 (11)	0.30612 (6)	0.0407 (3)
C22	0.15761 (12)	0.16050 (13)	0.26022 (6)	0.0460 (3)
H1	−0.0671 (14)	0.0616 (13)	0.3362 (8)	0.059 (5)*
H2	−0.0481 (16)	−0.0705 (14)	0.2563 (9)	0.064 (5)*
H3	0.1028 (16)	−0.0626 (15)	0.1779 (9)	0.072 (5)*
H4	0.2261 (16)	0.0911 (14)	0.1809 (9)	0.064 (5)*
H5	0.2969 (15)	0.2485 (14)	0.2323 (9)	0.063 (5)*
H6	0.2896 (14)	0.3731 (13)	0.3152 (8)	0.052 (4)*
H7	0.2025 (15)	0.5154 (14)	0.3456 (9)	0.061 (5)*
H8	0.2348 (17)	0.6545 (17)	0.4197 (9)	0.078 (6)*
H9	0.2034 (16)	0.6214 (15)	0.5318 (9)	0.072 (5)*
H10	0.1317 (15)	0.4579 (14)	0.5657 (9)	0.061 (5)*
H111	0.1505 (16)	0.2598 (14)	0.5937 (9)	0.066 (5)*
H211	0.0275 (16)	0.3171 (15)	0.5979 (9)	0.065 (5)*
H112	0.0824 (18)	0.0939 (17)	0.5720 (10)	0.080 (6)*
H212	−0.0247 (18)	0.1395 (16)	0.6174 (10)	0.078 (6)*
H213	−0.1360 (16)	0.1768 (14)	0.5263 (9)	0.063 (5)*
H113	−0.0650 (15)	0.0726 (15)	0.5003 (8)	0.062 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0345 (5)	0.0922 (9)	0.0550 (6)	−0.0056 (5)	−0.0033 (4)	−0.0090 (6)
C1	0.0493 (8)	0.0557 (9)	0.0421 (7)	−0.0045 (7)	−0.0031 (6)	0.0015 (6)
C2	0.0677 (10)	0.0571 (9)	0.0494 (8)	−0.0073 (8)	−0.0095 (7)	−0.0030 (8)
C3	0.0746 (11)	0.0626 (10)	0.0419 (8)	0.0080 (9)	−0.0056 (8)	−0.0069 (7)
C4	0.0606 (9)	0.0683 (11)	0.0386 (8)	0.0098 (8)	0.0006 (7)	−0.0006 (7)
C5	0.0480 (8)	0.0676 (10)	0.0424 (7)	−0.0007 (7)	0.0101 (7)	0.0055 (7)
C6	0.0441 (8)	0.0590 (9)	0.0441 (7)	−0.0073 (7)	0.0056 (6)	0.0078 (7)
C7	0.0548 (9)	0.0472 (8)	0.0617 (10)	−0.0091 (7)	0.0029 (8)	0.0086 (7)
C8	0.0586 (10)	0.0429 (9)	0.0863 (13)	−0.0105 (7)	0.0039 (9)	0.0031 (8)
C9	0.0489 (9)	0.0487 (9)	0.0781 (12)	−0.0064 (7)	−0.0007 (8)	−0.0156 (9)
C10	0.0440 (8)	0.0530 (9)	0.0528 (8)	−0.0016 (7)	−0.0018 (7)	−0.0100 (7)
C11	0.0530 (9)	0.0639 (10)	0.0376 (7)	−0.0017 (8)	0.0007 (6)	0.0020 (7)
C12	0.0705 (11)	0.0695 (12)	0.0448 (8)	−0.0083 (9)	0.0052 (8)	0.0148 (8)
C13	0.0537 (9)	0.0561 (10)	0.0480 (8)	−0.0114 (8)	0.0086 (7)	0.0052 (7)
C14	0.0353 (7)	0.0453 (8)	0.0428 (7)	−0.0025 (6)	−0.0005 (6)	−0.0013 (6)
C15	0.0361 (6)	0.0425 (7)	0.0400 (7)	−0.0012 (6)	0.0047 (5)	0.0009 (6)
C16	0.0351 (6)	0.0457 (7)	0.0378 (7)	0.0019 (6)	0.0013 (5)	0.0004 (6)
C17	0.0322 (6)	0.0431 (7)	0.0446 (7)	0.0011 (6)	−0.0017 (5)	−0.0005 (6)
C18	0.0347 (6)	0.0427 (7)	0.0460 (7)	−0.0019 (6)	−0.0006 (6)	0.0043 (6)
C19	0.0374 (7)	0.0447 (7)	0.0370 (6)	−0.0003 (6)	−0.0015 (5)	0.0078 (6)
C20	0.0349 (7)	0.0465 (7)	0.0332 (6)	0.0009 (6)	−0.0026 (5)	0.0063 (6)
C21	0.0415 (7)	0.0478 (7)	0.0330 (6)	0.0025 (6)	−0.0052 (5)	0.0049 (6)
C22	0.0478 (8)	0.0564 (8)	0.0340 (7)	0.0052 (7)	−0.0002 (6)	0.0053 (6)

Geometric parameters (Å, º)

O1—C14	1.2260 (16)	C11—C16	1.5125 (19)
C1—C2	1.372 (2)	C11—C12	1.527 (3)
C1—C21	1.414 (2)	C12—C13	1.529 (2)
C2—C3	1.405 (2)	C13—C15	1.5045 (19)
C3—C4	1.356 (3)	C14—C15	1.4575 (19)
C4—C22	1.419 (2)	C14—C20	1.4904 (18)
C5—C6	1.353 (2)	C15—C16	1.3453 (19)
C5—C22	1.412 (2)	C16—C17	1.4596 (19)
C6—C19	1.4297 (19)	C17—C18	1.4175 (19)
C7—C8	1.373 (2)	C18—C19	1.484 (2)
C7—C18	1.401 (2)	C19—C20	1.3878 (19)
C8—C9	1.376 (3)	C20—C21	1.4406 (19)
C9—C10	1.374 (2)	C21—C22	1.4200 (19)
C10—C17	1.404 (2)
C2—C1—C21	121.43 (15)	C15—C16—C11	109.61 (13)
C1—C2—C3	120.35 (17)	C17—C16—C11	122.49 (13)
C4—C3—C2	119.97 (16)	C10—C17—C18	118.26 (13)
C3—C4—C22	121.05 (16)	C10—C17—C16	117.48 (13)
C6—C5—C22	120.97 (14)	C18—C17—C16	124.22 (12)
C5—C6—C19	122.38 (15)	C7—C18—C17	117.59 (13)
C8—C7—C18	122.57 (16)	C7—C18—C19	117.74 (13)
C7—C8—C9	119.77 (16)	C17—C18—C19	124.48 (12)
C10—C9—C8	119.40 (16)	C20—C19—C6	117.67 (13)
C9—C10—C17	122.27 (16)	C20—C19—C18	125.90 (12)
C16—C11—C12	103.50 (13)	C6—C19—C18	116.43 (12)
C11—C12—C13	104.58 (13)	C19—C20—C21	121.07 (12)
C15—C13—C12	102.23 (13)	C19—C20—C14	121.38 (12)
O1—C14—C15	121.13 (13)	C21—C20—C14	117.51 (12)
O1—C14—C20	121.47 (12)	C1—C21—C22	117.64 (13)
C15—C14—C20	117.08 (11)	C1—C21—C20	123.32 (13)
C16—C15—C14	125.97 (13)	C22—C21—C20	118.95 (13)
C16—C15—C13	112.05 (12)	C5—C22—C4	121.53 (14)
C14—C15—C13	121.57 (12)	C5—C22—C21	118.91 (13)
C15—C16—C17	126.94 (13)	C4—C22—C21	119.54 (14)
C21—C1—C2—C3	−0.4 (2)	C10—C17—C18—C19	170.55 (13)
C1—C2—C3—C4	0.7 (3)	C16—C17—C18—C19	−11.7 (2)
C2—C3—C4—C22	0.1 (3)	C5—C6—C19—C20	−1.1 (2)
C22—C5—C6—C19	−0.9 (2)	C5—C6—C19—C18	179.53 (14)
C18—C7—C8—C9	0.6 (3)	C7—C18—C19—C20	−145.12 (14)
C7—C8—C9—C10	−1.8 (3)	C17—C18—C19—C20	40.0 (2)
C8—C9—C10—C17	−0.1 (3)	C7—C18—C19—C6	34.24 (19)
C16—C11—C12—C13	−26.59 (18)	C17—C18—C19—C6	−140.63 (13)
C11—C12—C13—C15	27.14 (18)	C6—C19—C20—C21	2.55 (19)
O1—C14—C15—C16	−135.85 (16)	C18—C19—C20—C21	−178.10 (12)
C20—C14—C15—C16	50.5 (2)	C6—C19—C20—C14	−179.91 (12)
O1—C14—C15—C13	36.2 (2)	C18—C19—C20—C14	−0.6 (2)
C20—C14—C15—C13	−137.42 (14)	O1—C14—C20—C19	131.77 (15)
C12—C13—C15—C16	−18.48 (18)	C15—C14—C20—C19	−54.63 (18)
C12—C13—C15—C14	168.44 (14)	O1—C14—C20—C21	−50.6 (2)
C14—C15—C16—C17	5.5 (2)	C15—C14—C20—C21	123.00 (13)
C13—C15—C16—C17	−167.24 (13)	C2—C1—C21—C22	−0.7 (2)
C14—C15—C16—C11	174.39 (14)	C2—C1—C21—C20	−177.19 (14)
C13—C15—C16—C11	1.68 (18)	C19—C20—C21—C1	174.34 (13)
C12—C11—C16—C15	15.95 (18)	C14—C20—C21—C1	−3.29 (19)
C12—C11—C16—C17	−174.53 (14)	C19—C20—C21—C22	−2.15 (19)
C9—C10—C17—C18	3.3 (2)	C14—C20—C21—C22	−179.78 (12)
C9—C10—C17—C16	−174.60 (14)	C6—C5—C22—C4	−176.62 (15)
C15—C16—C17—C10	149.85 (14)	C6—C5—C22—C21	1.3 (2)
C11—C16—C17—C10	−17.8 (2)	C3—C4—C22—C5	176.69 (15)
C15—C16—C17—C18	−27.9 (2)	C3—C4—C22—C21	−1.2 (2)
C11—C16—C17—C18	164.49 (13)	C1—C21—C22—C5	−176.50 (13)
C8—C7—C18—C17	2.5 (2)	C20—C21—C22—C5	0.2 (2)
C8—C7—C18—C19	−172.70 (15)	C1—C21—C22—C4	1.5 (2)
C10—C17—C18—C7	−4.3 (2)	C20—C21—C22—C4	178.15 (13)
C16—C17—C18—C7	173.39 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	1.002 (17)	2.338 (17)	2.937 (2)	117.4 (12)
C5—H5···O1^i	0.972 (18)	2.617 (18)	3.4993 (19)	151.0 (14)
C4—H4···O1^i	0.973 (19)	2.714 (19)	3.604 (2)	152.3 (14)
C9—H9···O1^ii	0.972 (19)	2.768 (19)	3.653 (2)	151.7 (15)
C11—H111···O1^iii	1.038 (19)	2.652 (19)	3.658 (2)	163.3 (14)

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x, −y+1, −z+1; (iii) x+1/2, −y+1/2, −z+1.