Methyl 3,5,5,6,8,8-hexa-methyl-5,6,7,8-tetra-hydro-naphthalene-2-carboxyl-ate (AHTN-COOMe).

Crystals of the title compound, C(18)H(26)O(2), were grown from ethyl acetate. Due to the racemic precursor, the title compound is also obtained as a racemate. Disorder was observed during structure refinement, originating from two possible half-chair conformations of the non-aromatic ring. The disorder was refined by introducing split positions in the cyclo-hexane ring regarding the two possible R and S-enantiomers at the chiral CH group [ratio 0.744 (3):0.256 (3)]. The crystal structure features pairs of inversion-related molecules connected by pairs of non-classical C-H⋯O hydrogen bonds.

Related literature

For the occurrence of the title compound in human breast milk and the fatty tissue of fish, see: Valdersnes et al. (2006 ▶). The title compound is the product of an esterification of 3,5,5,6,8,8-hexa­methyl-5,6,7,8-tetra­hydro­naphthalene-2-carb­oxy­lic acid (AHTN—COOH) with methanol. For the synthesis of the acid, see: Kuhlich et al. (2010 ▶); Valdersnes et al. (2006 ▶). For the crystal structures of AHTN and AHTN–COOH, see: De Ridder et al. (1990 ▶) and Kuhlich et al. (2010 ▶), respectively. For the environmental occurrence and estrogenic activity of AHTN, see: Heberer (2003 ▶); Bitsch et al. (2002 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H26O2

M = 274.39

Monoclinic,

a = 11.5049 (11) Å

b = 11.9482 (5) Å

c = 12.1078 (13) Å

β = 102.612 (5)°

V = 1624.2 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.55 mm−1

T = 193 K

0.45 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

5083 measured reflections

3062 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections every 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.03

3062 reflections

216 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002601/zl2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002601/zl2346Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H26O2	F(000) = 600
Mr = 274.39	Dx = 1.122 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.5049 (11) Å	θ = 65–69°
b = 11.9482 (5) Å	µ = 0.55 mm−1
c = 12.1078 (13) Å	T = 193 K
β = 102.612 (5)°	Block, colourless
V = 1624.2 (2) Å3	0.45 × 0.40 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.047
Radiation source: rotating anode	θmax = 69.8°, θmin = 4.8°
graphite	h = 0→14
ω/2θ scans	k = −14→14
5083 measured reflections	l = −14→14
3062 independent reflections	3 standard reflections every 60 min
2856 reflections with I > 2σ(I)	intensity decay: 3%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0889P)2 + 0.4305P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3062 reflections	Δρmax = 0.29 e Å−3
216 parameters	Δρmin = −0.26 e Å−3
10 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.34558 (10)	1.32637 (9)	−0.02324 (9)	0.0454 (3)
O2	0.44327 (15)	1.40647 (10)	0.13483 (11)	0.0711 (5)
C1	0.40482 (12)	1.32335 (11)	0.08442 (12)	0.0353 (3)
C2	0.41364 (11)	1.20805 (11)	0.13210 (10)	0.0283 (3)
C3	0.34903 (11)	1.12216 (11)	0.06975 (10)	0.0284 (3)
H23	0.2999	1.1396	−0.0020	0.034*
C4	0.35277 (10)	1.01170 (11)	0.10740 (10)	0.0267 (3)
C5	0.42442 (11)	0.98674 (11)	0.21369 (10)	0.0280 (3)
C6	0.48890 (11)	1.07419 (11)	0.27540 (10)	0.0310 (3)
H4	0.5373	1.0571	0.3476	0.037*
C7	0.48699 (11)	1.18407 (11)	0.23842 (10)	0.0297 (3)
C8	0.56520 (13)	1.26927 (13)	0.31130 (12)	0.0412 (4)
H1	0.6091	1.2331	0.3806	0.062*
H2	0.5156	1.3295	0.3310	0.062*
H3	0.6217	1.3005	0.2696	0.062*
C9	0.43809 (13)	0.86813 (12)	0.26390 (11)	0.0358 (4)
C10	0.33564 (19)	0.79143 (16)	0.19751 (16)	0.0364 (5)	0.744 (3)
H16	0.2599	0.8165	0.2176	0.044*	0.744 (3)
C11	0.32069 (18)	0.80706 (15)	0.07020 (16)	0.0352 (4)	0.744 (3)
H11	0.3979	0.7929	0.0493	0.042*	0.744 (3)
H12	0.2627	0.7515	0.0302	0.042*	0.744 (3)
C15	0.3518 (4)	0.6672 (3)	0.2281 (5)	0.0516 (9)	0.744 (3)
H13	0.2785	0.6265	0.1949	0.077*	0.744 (3)
H14	0.3692	0.6587	0.3106	0.077*	0.744 (3)
H15	0.4180	0.6368	0.1984	0.077*	0.744 (3)
C10B	0.3875 (6)	0.7792 (5)	0.1773 (5)	0.0364 (5)	0.256 (3)
H16B	0.4408	0.7776	0.1222	0.044*	0.256 (3)
C11B	0.2689 (5)	0.8159 (4)	0.1118 (5)	0.0352 (4)	0.256 (3)
H11B	0.2177	0.8350	0.1651	0.042*	0.256 (3)
H12B	0.2307	0.7532	0.0638	0.042*	0.256 (3)
C15B	0.3853 (14)	0.6606 (11)	0.2212 (16)	0.0516 (9)	0.256 (3)
H13B	0.4661	0.6383	0.2595	0.077*	0.256 (3)
H14B	0.3559	0.6098	0.1577	0.077*	0.256 (3)
H15B	0.3327	0.6569	0.2747	0.077*	0.256 (3)
C12	0.27785 (11)	0.92416 (11)	0.03173 (11)	0.0318 (3)
C13	0.1469 (4)	0.9422 (4)	0.0305 (4)	0.0414 (9)	0.744 (3)
H5	0.0990	0.8866	−0.0190	0.062*	0.744 (3)
H6	0.1232	1.0176	0.0023	0.062*	0.744 (3)
H7	0.1339	0.9342	0.1075	0.062*	0.744 (3)
C14	0.2948 (2)	0.93749 (19)	−0.09371 (18)	0.0374 (5)	0.744 (3)
H8	0.3800	0.9388	−0.0936	0.056*	0.744 (3)
H9	0.2580	1.0076	−0.1258	0.056*	0.744 (3)
H10	0.2570	0.8744	−0.1395	0.056*	0.744 (3)
C16	0.4257 (4)	0.8693 (6)	0.3874 (3)	0.0576 (11)	0.744 (3)
H17	0.4953	0.9059	0.4345	0.086*	0.744 (3)
H18	0.4202	0.7922	0.4135	0.086*	0.744 (3)
H19	0.3535	0.9104	0.3930	0.086*	0.744 (3)
C17	0.5617 (2)	0.8238 (2)	0.2576 (2)	0.0464 (6)	0.744 (3)
H20	0.5676	0.8189	0.1782	0.070*	0.744 (3)
H21	0.5734	0.7494	0.2923	0.070*	0.744 (3)
H22	0.6230	0.8749	0.2982	0.070*	0.744 (3)
C13B	0.1450 (11)	0.9619 (14)	0.0068 (14)	0.0414 (9)	0.256 (3)
H5B	0.0939	0.8991	−0.0254	0.062*	0.256 (3)
H6B	0.1334	1.0242	−0.0473	0.062*	0.256 (3)
H7B	0.1241	0.9862	0.0773	0.062*	0.256 (3)
C14B	0.3189 (7)	0.8985 (6)	−0.0673 (6)	0.0374 (5)	0.256 (3)
H8B	0.3208	0.9670	−0.1115	0.056*	0.256 (3)
H9B	0.2652	0.8441	−0.1128	0.056*	0.256 (3)
H10B	0.3993	0.8668	−0.0462	0.056*	0.256 (3)
C16B	0.3894 (15)	0.876 (2)	0.3749 (13)	0.0576 (11)	0.256 (3)
H17B	0.4310	0.9355	0.4231	0.086*	0.256 (3)
H18B	0.4029	0.8042	0.4155	0.086*	0.256 (3)
H19B	0.3038	0.8918	0.3554	0.086*	0.256 (3)
C17B	0.5738 (8)	0.8426 (8)	0.3014 (7)	0.0464 (6)	0.256 (3)
H20B	0.6116	0.8534	0.2371	0.070*	0.256 (3)
H21B	0.5851	0.7651	0.3279	0.070*	0.256 (3)
H22B	0.6101	0.8934	0.3629	0.070*	0.256 (3)
C18	0.33250 (17)	1.43507 (14)	−0.07628 (16)	0.0561 (5)
H24	0.2983	1.4873	−0.0297	0.084*
H25	0.2796	1.4293	−0.1514	0.084*
H26	0.4107	1.4624	−0.0838	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0551 (7)	0.0345 (6)	0.0423 (6)	−0.0050 (5)	0.0009 (5)	0.0096 (4)
O2	0.1106 (12)	0.0323 (6)	0.0585 (8)	−0.0166 (7)	−0.0076 (7)	0.0010 (5)
C1	0.0362 (7)	0.0302 (7)	0.0399 (7)	−0.0030 (5)	0.0091 (6)	0.0000 (5)
C2	0.0269 (6)	0.0288 (7)	0.0313 (6)	0.0003 (5)	0.0108 (5)	−0.0009 (5)
C3	0.0272 (6)	0.0312 (7)	0.0270 (6)	0.0007 (5)	0.0066 (5)	−0.0006 (5)
C4	0.0252 (6)	0.0293 (7)	0.0275 (6)	0.0000 (5)	0.0101 (5)	−0.0018 (5)
C5	0.0292 (6)	0.0312 (7)	0.0268 (6)	0.0023 (5)	0.0130 (5)	0.0012 (5)
C6	0.0320 (7)	0.0372 (7)	0.0243 (6)	0.0022 (5)	0.0072 (5)	−0.0009 (5)
C7	0.0277 (6)	0.0342 (7)	0.0289 (6)	−0.0004 (5)	0.0101 (5)	−0.0066 (5)
C8	0.0415 (8)	0.0406 (8)	0.0388 (7)	−0.0035 (6)	0.0031 (6)	−0.0098 (6)
C9	0.0452 (8)	0.0337 (7)	0.0306 (7)	0.0020 (6)	0.0132 (5)	0.0062 (5)
C10	0.0429 (12)	0.0309 (9)	0.0411 (10)	−0.0002 (9)	0.0216 (8)	0.0049 (7)
C11	0.0417 (10)	0.0276 (9)	0.0390 (10)	−0.0032 (7)	0.0149 (7)	−0.0046 (7)
C15	0.066 (3)	0.0331 (10)	0.0607 (13)	−0.0013 (14)	0.0255 (19)	0.0079 (8)
C10B	0.0429 (12)	0.0309 (9)	0.0411 (10)	−0.0002 (9)	0.0216 (8)	0.0049 (7)
C11B	0.0417 (10)	0.0276 (9)	0.0390 (10)	−0.0032 (7)	0.0149 (7)	−0.0046 (7)
C15B	0.066 (3)	0.0331 (10)	0.0607 (13)	−0.0013 (14)	0.0255 (19)	0.0079 (8)
C12	0.0322 (7)	0.0292 (7)	0.0340 (7)	−0.0025 (5)	0.0073 (5)	−0.0034 (5)
C13	0.0314 (8)	0.043 (2)	0.052 (2)	−0.0091 (10)	0.0133 (11)	−0.0071 (14)
C14	0.0466 (13)	0.0345 (13)	0.0325 (11)	−0.0042 (9)	0.0117 (9)	−0.0053 (8)
C16	0.091 (3)	0.0511 (14)	0.0374 (14)	0.006 (3)	0.029 (2)	0.0144 (12)
C17	0.0529 (12)	0.0383 (13)	0.0484 (16)	0.0109 (9)	0.0119 (13)	0.0057 (12)
C13B	0.0314 (8)	0.043 (2)	0.052 (2)	−0.0091 (10)	0.0133 (11)	−0.0071 (14)
C14B	0.0466 (13)	0.0345 (13)	0.0325 (11)	−0.0042 (9)	0.0117 (9)	−0.0053 (8)
C16B	0.091 (3)	0.0511 (14)	0.0374 (14)	0.006 (3)	0.029 (2)	0.0144 (12)
C17B	0.0529 (12)	0.0383 (13)	0.0484 (16)	0.0109 (9)	0.0119 (13)	0.0057 (12)
C18	0.0646 (11)	0.0412 (9)	0.0583 (10)	−0.0050 (8)	0.0038 (8)	0.0200 (7)

O1—C1	1.3330 (17)	C11B—H11B	0.9900
O1—C18	1.4422 (18)	C11B—H12B	0.9900
O2—C1	1.1986 (18)	C15B—H13B	0.9800
C1—C2	1.4886 (18)	C15B—H14B	0.9800
C2—C3	1.3895 (18)	C15B—H15B	0.9800
C2—C7	1.4060 (18)	C12—C14B	1.415 (7)
C3—C4	1.3939 (18)	C12—C13	1.519 (4)
C3—H23	0.9500	C12—C13B	1.559 (12)
C4—C5	1.4005 (18)	C12—C14	1.581 (2)
C4—C12	1.5270 (17)	C13—H5	0.9800
C5—C6	1.3994 (18)	C13—H6	0.9800
C5—C9	1.5365 (18)	C13—H7	0.9800
C6—C7	1.3858 (19)	C14—H8	0.9800
C6—H4	0.9500	C14—H9	0.9800
C7—C8	1.5092 (18)	C14—H10	0.9800
C8—H1	0.9800	C16—H17	0.9800
C8—H2	0.9800	C16—H18	0.9800
C8—H3	0.9800	C16—H19	0.9800
C9—C10B	1.517 (6)	C17—H20	0.9800
C9—C16	1.532 (4)	C17—H21	0.9800
C9—C17	1.535 (3)	C17—H22	0.9800
C9—C17B	1.558 (9)	C13B—H5B	0.9800
C9—C16B	1.567 (12)	C13B—H6B	0.9800
C9—C10	1.569 (2)	C13B—H7B	0.9800
C10—C11	1.525 (3)	C14B—H8B	0.9800
C10—C15	1.531 (4)	C14B—H9B	0.9800
C10—H16	1.0000	C14B—H10B	0.9800
C11—C12	1.522 (2)	C16B—H17B	0.9800
C11—H11	0.9900	C16B—H18B	0.9800
C11—H12	0.9900	C16B—H19B	0.9800
C15—H13	0.9800	C17B—H20B	0.9800
C15—H14	0.9800	C17B—H21B	0.9800
C15—H15	0.9800	C17B—H22B	0.9800
C10B—C11B	1.487 (8)	C18—H24	0.9800
C10B—C15B	1.515 (13)	C18—H25	0.9800
C10B—H16B	1.0000	C18—H26	0.9800
C11B—C12	1.633 (5)
C1—O1—C18	116.18 (12)	C12—C11B—H12B	109.1
O2—C1—O1	121.91 (13)	H11B—C11B—H12B	107.9
O2—C1—C2	125.66 (13)	C10B—C15B—H13B	109.5
O1—C1—C2	112.42 (11)	C10B—C15B—H14B	109.5
C3—C2—C7	119.33 (12)	H13B—C15B—H14B	109.5
C3—C2—C1	119.32 (11)	C10B—C15B—H15B	109.5
C7—C2—C1	121.35 (12)	H13B—C15B—H15B	109.5
C2—C3—C4	123.16 (11)	H14B—C15B—H15B	109.5
C2—C3—H23	118.4	C14B—C12—C13	122.5 (4)
C4—C3—H23	118.4	C14B—C12—C11	85.1 (3)
C3—C4—C5	118.17 (11)	C13—C12—C11	112.82 (19)
C3—C4—C12	118.64 (11)	C14B—C12—C4	114.0 (3)
C5—C4—C12	123.19 (12)	C13—C12—C4	109.7 (2)
C6—C5—C4	117.95 (12)	C11—C12—C4	110.08 (12)
C6—C5—C9	118.74 (11)	C14B—C12—C13B	113.2 (7)
C4—C5—C9	123.29 (12)	C4—C12—C13B	108.6 (7)
C7—C6—C5	124.45 (11)	C13—C12—C14	107.86 (18)
C7—C6—H4	117.8	C11—C12—C14	106.67 (13)
C5—C6—H4	117.8	C4—C12—C14	109.60 (12)
C6—C7—C2	116.93 (11)	C13B—C12—C14	96.1 (6)
C6—C7—C8	119.00 (12)	C14B—C12—C11B	114.1 (4)
C2—C7—C8	124.04 (12)	C13—C12—C11B	85.8 (2)
C7—C8—H1	109.5	C4—C12—C11B	106.7 (2)
C7—C8—H2	109.5	C13B—C12—C11B	99.1 (6)
H1—C8—H2	109.5	C14—C12—C11B	133.4 (2)
C7—C8—H3	109.5	C12—C13—H5	109.5
H1—C8—H3	109.5	C12—C13—H6	109.5
H2—C8—H3	109.5	C12—C13—H7	109.5
C10B—C9—C16	125.2 (4)	C12—C14—H8	109.5
C10B—C9—C17	86.8 (3)	C12—C14—H9	109.5
C16—C9—C17	109.67 (19)	C12—C14—H10	109.5
C10B—C9—C5	112.5 (2)	C9—C16—H17	109.5
C16—C9—C5	110.8 (3)	C9—C16—H18	109.5
C17—C9—C5	108.32 (14)	C9—C16—H19	109.5
C10B—C9—C17B	105.9 (4)	C9—C17—H20	109.5
C16—C9—C17B	91.1 (4)	C9—C17—H21	109.5
C5—C9—C17B	107.8 (4)	C9—C17—H22	109.5
C10B—C9—C16B	118.5 (10)	C12—C13B—H5B	109.5
C17—C9—C16B	124.8 (6)	C12—C13B—H6B	109.5
C5—C9—C16B	105.2 (9)	H5B—C13B—H6B	109.5
C17B—C9—C16B	106.5 (7)	C12—C13B—H7B	109.5
C17—C9—C10	111.94 (15)	H5B—C13B—H7B	109.5
C5—C9—C10	109.60 (12)	H6B—C13B—H7B	109.5
C17B—C9—C10	128.9 (4)	C12—C14B—H8B	109.5
C16B—C9—C10	95.9 (9)	C12—C14B—H9B	109.5
C11—C10—C15	110.1 (2)	H8B—C14B—H9B	109.5
C11—C10—C9	110.65 (14)	C12—C14B—H10B	109.5
C15—C10—C9	113.8 (2)	H8B—C14B—H10B	109.5
C11—C10—H16	107.3	H9B—C14B—H10B	109.5
C15—C10—H16	107.3	C9—C16B—H17B	109.5
C9—C10—H16	107.3	C9—C16B—H18B	109.5
C12—C11—C10	112.30 (14)	H17B—C16B—H18B	109.5
C12—C11—H11	109.1	C9—C16B—H19B	109.5
C10—C11—H11	109.1	H17B—C16B—H19B	109.5
C12—C11—H12	109.1	H18B—C16B—H19B	109.5
C10—C11—H12	109.1	C9—C17B—H20B	109.5
H11—C11—H12	107.9	C9—C17B—H21B	109.5
C11B—C10B—C15B	112.3 (8)	H20B—C17B—H21B	109.5
C11B—C10B—C9	109.3 (4)	C9—C17B—H22B	109.5
C15B—C10B—C9	116.5 (9)	H20B—C17B—H22B	109.5
C11B—C10B—H16B	106.0	H21B—C17B—H22B	109.5
C15B—C10B—H16B	106.0	O1—C18—H24	109.5
C9—C10B—H16B	106.0	O1—C18—H25	109.5
C10B—C11B—C12	112.4 (4)	H24—C18—H25	109.5
C10B—C11B—H11B	109.1	O1—C18—H26	109.5
C12—C11B—H11B	109.1	H24—C18—H26	109.5
C10B—C11B—H12B	109.1	H25—C18—H26	109.5
C18—O1—C1—O2	1.2 (2)	C17B—C9—C10—C15	36.1 (5)
C18—O1—C1—C2	179.86 (13)	C16B—C9—C10—C15	−80.7 (8)
O2—C1—C2—C3	169.86 (15)	C15—C10—C11—C12	167.6 (2)
O1—C1—C2—C3	−8.72 (18)	C9—C10—C11—C12	−65.6 (2)
O2—C1—C2—C7	−10.8 (2)	C16—C9—C10B—C11B	94.2 (5)
O1—C1—C2—C7	170.60 (11)	C17—C9—C10B—C11B	−153.9 (4)
C7—C2—C3—C4	0.10 (18)	C5—C9—C10B—C11B	−45.4 (5)
C1—C2—C3—C4	179.43 (11)	C17B—C9—C10B—C11B	−162.8 (5)
C2—C3—C4—C5	0.59 (18)	C16B—C9—C10B—C11B	77.8 (9)
C2—C3—C4—C12	179.94 (11)	C10—C9—C10B—C11B	43.7 (4)
C3—C4—C5—C6	−0.56 (17)	C16—C9—C10B—C15B	−34.4 (8)
C12—C4—C5—C6	−179.88 (11)	C17—C9—C10B—C15B	77.5 (7)
C3—C4—C5—C9	−178.83 (11)	C5—C9—C10B—C15B	−174.0 (6)
C12—C4—C5—C9	1.85 (18)	C17B—C9—C10B—C15B	68.5 (8)
C4—C5—C6—C7	−0.15 (19)	C16B—C9—C10B—C15B	−50.9 (10)
C9—C5—C6—C7	178.20 (11)	C10—C9—C10B—C15B	−85.0 (8)
C5—C6—C7—C2	0.83 (19)	C15B—C10B—C11B—C12	−161.7 (8)
C5—C6—C7—C8	−177.28 (12)	C9—C10B—C11B—C12	67.4 (5)
C3—C2—C7—C6	−0.78 (17)	C10—C11—C12—C14B	162.2 (4)
C1—C2—C7—C6	179.90 (11)	C10—C11—C12—C13	−74.5 (3)
C3—C2—C7—C8	177.23 (12)	C10—C11—C12—C4	48.37 (18)
C1—C2—C7—C8	−2.10 (19)	C10—C11—C12—C13B	−83.0 (8)
C6—C5—C9—C10B	−166.3 (3)	C10—C11—C12—C14	167.20 (16)
C4—C5—C9—C10B	12.0 (3)	C10—C11—C12—C11B	−41.0 (4)
C6—C5—C9—C16	48.2 (2)	C3—C4—C12—C14B	69.9 (3)
C4—C5—C9—C16	−133.5 (2)	C5—C4—C12—C14B	−110.8 (3)
C6—C5—C9—C17	−72.09 (16)	C3—C4—C12—C13	−71.72 (18)
C4—C5—C9—C17	106.17 (16)	C5—C4—C12—C13	107.60 (17)
C6—C5—C9—C17B	−50.0 (3)	C3—C4—C12—C11	163.56 (12)
C4—C5—C9—C17B	128.3 (3)	C5—C4—C12—C11	−17.12 (17)
C6—C5—C9—C16B	63.4 (8)	C3—C4—C12—C13B	−57.3 (6)
C4—C5—C9—C16B	−118.4 (8)	C5—C4—C12—C13B	122.0 (6)
C6—C5—C9—C10	165.52 (12)	C3—C4—C12—C14	46.53 (17)
C4—C5—C9—C10	−16.23 (17)	C5—C4—C12—C14	−134.15 (14)
C16—C9—C10—C11	166.1 (2)	C3—C4—C12—C11B	−163.2 (2)
C17—C9—C10—C11	−74.04 (19)	C5—C4—C12—C11B	16.1 (3)
C5—C9—C10—C11	46.17 (18)	C10B—C11B—C12—C14B	75.9 (6)
C17B—C9—C10—C11	−88.6 (5)	C10B—C11B—C12—C13	−160.2 (5)
C16B—C9—C10—C11	154.6 (7)	C10B—C11B—C12—C11	50.5 (4)
C16—C9—C10—C15	−69.3 (3)	C10B—C11B—C12—C4	−50.9 (5)
C17—C9—C10—C15	50.6 (2)	C10B—C11B—C12—C13B	−163.5 (8)
C5—C9—C10—C15	170.84 (18)	C10B—C11B—C12—C14	89.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H23···O1	0.95	2.32	2.6839 (17)	103
C18—H26···O2i	0.98	2.47	3.397 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H26⋯O2i	0.98	2.47	3.397 (2)	157

Symmetry code: (i) .