1-(Hydroxy-meth-yl)pyrene.

The asymmetric unit of the title compound, C(17)H(12)O, contains two molecules, in which the fused aromatic ring systems are almost planar [maximum deviations = 0.0529 (9) and 0.0256 (9) Å]. In the crystal, aromatic π-π stacking inter-actions (perpendicular distance of centroids of about 3.4 Å) and strong O-H⋯O hydrogen bonds result in a helical arrangement of pyrenyl dimers.

Related literature

For the solid–state structures of pyrenes, see: Robertson & White (1947 ▶); Camerman & Trotter (1965 ▶); Allmann (1970 ▶); Hazell et al. (1972 ▶); Kai et al. (1978 ▶); Frampton et al. (2000 ▶). For the synthesis and structures of pyrene derivatives, see: Steward (1960 ▶); Gruber et al. (2006 ▶, 2008 ▶, 2009 ▶). For the use of pyrenes in fluorescence sensors, see: Bren (2001 ▶).

Experimental

Crystal data

C17H12O

M = 232.27

Monoclinic,

a = 19.9182 (6) Å

b = 8.8880 (3) Å

c = 13.0882 (4) Å

β = 91.719 (2)°

V = 2316.00 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.59 × 0.29 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

29632 measured reflections

5051 independent reflections

3801 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.06

5051 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002424/rk2186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002424/rk2186Isup2.hkl

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

C17H12O	F(000) = 976
Mr = 232.27	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Melting point: 393 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 19.9182 (6) Å	Cell parameters from 8740 reflections
b = 8.8880 (3) Å	θ = 2.5–32.3°
c = 13.0882 (4) Å	µ = 0.08 mm−1
β = 91.719 (2)°	T = 153 K
V = 2316.00 (13) Å3	Plate, colourless
Z = 8	0.59 × 0.29 × 0.12 mm

Bruker APEXII CCD area-detector diffractometer	3801 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.026
graphite	θmax = 27.0°, θmin = 3.0°
φ and ω scans	h = −25→25
29632 measured reflections	k = −11→10
5051 independent reflections	l = −16→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.2704P] where P = (Fo2 + 2Fc2)/3
5051 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.53989 (4)	−0.02633 (10)	0.21742 (7)	0.0412 (2)
H1	0.5295	−0.0899	0.2617	0.062*
C1	0.65534 (6)	0.05248 (12)	0.26246 (8)	0.0262 (2)
C2	0.63001 (6)	0.15072 (13)	0.33402 (8)	0.0316 (3)
H2	0.5828	0.1582	0.3409	0.038*
C3	0.67218 (6)	0.23825 (13)	0.39567 (8)	0.0336 (3)
H3	0.6534	0.3036	0.4447	0.040*
C4	0.74142 (6)	0.23177 (12)	0.38682 (8)	0.0296 (3)
C5	0.78651 (7)	0.32180 (13)	0.44853 (9)	0.0392 (3)
H5	0.7688	0.3864	0.4989	0.047*
C6	0.85288 (7)	0.31708 (14)	0.43697 (10)	0.0444 (3)
H6	0.8812	0.3781	0.4794	0.053*
C7	0.88234 (7)	0.22197 (14)	0.36198 (10)	0.0388 (3)
C8	0.95132 (7)	0.21558 (18)	0.34778 (12)	0.0540 (4)
H8	0.9807	0.2747	0.3899	0.065*
C9	0.97759 (7)	0.1249 (2)	0.27363 (13)	0.0606 (5)
H9	1.0247	0.1236	0.2645	0.073*
C10	0.93612 (7)	0.03560 (18)	0.21215 (11)	0.0494 (4)
H10	0.9550	−0.0256	0.1609	0.059*
C11	0.86674 (6)	0.03471 (14)	0.22482 (9)	0.0334 (3)
C12	0.82208 (6)	−0.05924 (13)	0.16581 (9)	0.0334 (3)
H12	0.8400	−0.1256	0.1167	0.040*
C13	0.75524 (6)	−0.05603 (12)	0.17800 (8)	0.0282 (3)
H13	0.7272	−0.1204	0.1374	0.034*
C14	0.72512 (5)	0.04227 (11)	0.25087 (7)	0.0236 (2)
C15	0.76866 (6)	0.13372 (11)	0.31289 (8)	0.0250 (2)
C16	0.83916 (6)	0.12977 (12)	0.29987 (8)	0.0296 (3)
C17	0.60896 (6)	−0.04252 (14)	0.19512 (9)	0.0335 (3)
H17A	0.6153	−0.0146	0.1228	0.040*
H17B	0.6218	−0.1496	0.2032	0.040*
O1A	0.48228 (4)	0.26209 (9)	0.65830 (6)	0.0368 (2)
H1A	0.4998	0.3385	0.6859	0.055*
C1A	0.41705 (5)	0.19195 (13)	0.50620 (8)	0.0286 (3)
C2A	0.43258 (6)	0.08575 (14)	0.43237 (9)	0.0343 (3)
H2A	0.4781	0.0724	0.4148	0.041*
C3A	0.38356 (6)	−0.00083 (14)	0.38391 (8)	0.0337 (3)
H3A	0.3959	−0.0728	0.3342	0.040*
C4A	0.31636 (6)	0.01636 (12)	0.40716 (8)	0.0277 (2)
C5A	0.26394 (7)	−0.06959 (13)	0.35757 (8)	0.0341 (3)
H5A	0.2754	−0.1425	0.3080	0.041*
C6A	0.19914 (7)	−0.04986 (13)	0.37933 (9)	0.0360 (3)
H6A	0.1658	−0.1081	0.3442	0.043*
C7A	0.17913 (6)	0.05748 (13)	0.45456 (8)	0.0308 (3)
C8A	0.11218 (6)	0.08017 (15)	0.47954 (10)	0.0397 (3)
H8A	0.0779	0.0234	0.4455	0.048*
C9A	0.09507 (6)	0.18397 (16)	0.55308 (10)	0.0426 (3)
H9A	0.0492	0.1978	0.5688	0.051*
C10A	0.14416 (6)	0.26767 (15)	0.60382 (9)	0.0371 (3)
H10A	0.1317	0.3383	0.6543	0.045*
C11A	0.21194 (6)	0.24959 (12)	0.58179 (8)	0.0281 (3)
C12A	0.26408 (6)	0.33496 (13)	0.63165 (8)	0.0305 (3)
H12A	0.2526	0.4059	0.6826	0.037*
C13A	0.32911 (6)	0.31781 (12)	0.60855 (8)	0.0286 (3)
H13A	0.3622	0.3777	0.6429	0.034*
C14A	0.34959 (5)	0.21105 (12)	0.53313 (8)	0.0245 (2)
C15A	0.29880 (5)	0.12329 (11)	0.48278 (7)	0.0232 (2)
C16A	0.23004 (5)	0.14309 (12)	0.50639 (8)	0.0250 (2)
C17A	0.47224 (6)	0.28837 (15)	0.55113 (9)	0.0370 (3)
H17C	0.5145	0.2669	0.5159	0.044*
H17D	0.4609	0.3956	0.5397	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0302 (5)	0.0379 (5)	0.0551 (6)	−0.0008 (4)	−0.0045 (4)	0.0141 (4)
C1	0.0342 (6)	0.0209 (5)	0.0234 (5)	0.0014 (5)	−0.0018 (4)	0.0054 (4)
C2	0.0356 (6)	0.0297 (6)	0.0297 (6)	0.0062 (5)	0.0051 (5)	0.0060 (5)
C3	0.0529 (8)	0.0252 (6)	0.0231 (6)	0.0098 (5)	0.0058 (5)	−0.0004 (5)
C4	0.0489 (7)	0.0184 (6)	0.0211 (5)	0.0018 (5)	−0.0035 (5)	0.0024 (4)
C5	0.0675 (9)	0.0225 (6)	0.0269 (6)	−0.0012 (6)	−0.0102 (6)	−0.0014 (5)
C6	0.0669 (10)	0.0280 (7)	0.0369 (7)	−0.0142 (6)	−0.0201 (6)	0.0039 (5)
C7	0.0451 (7)	0.0328 (7)	0.0377 (7)	−0.0109 (6)	−0.0120 (5)	0.0143 (5)
C8	0.0460 (8)	0.0608 (10)	0.0545 (9)	−0.0216 (7)	−0.0128 (7)	0.0200 (8)
C9	0.0329 (7)	0.0859 (12)	0.0627 (10)	−0.0102 (8)	−0.0017 (7)	0.0288 (9)
C10	0.0401 (8)	0.0603 (9)	0.0481 (8)	0.0083 (7)	0.0065 (6)	0.0171 (7)
C11	0.0344 (6)	0.0344 (7)	0.0316 (6)	0.0045 (5)	0.0012 (5)	0.0120 (5)
C12	0.0445 (7)	0.0297 (6)	0.0262 (6)	0.0108 (5)	0.0044 (5)	0.0020 (5)
C13	0.0392 (7)	0.0224 (6)	0.0229 (5)	0.0024 (5)	−0.0027 (4)	−0.0003 (4)
C14	0.0342 (6)	0.0176 (5)	0.0188 (5)	0.0018 (4)	−0.0016 (4)	0.0033 (4)
C15	0.0371 (6)	0.0177 (5)	0.0202 (5)	0.0015 (4)	−0.0030 (4)	0.0050 (4)
C16	0.0374 (7)	0.0244 (6)	0.0268 (6)	−0.0026 (5)	−0.0049 (5)	0.0102 (4)
C17	0.0322 (6)	0.0327 (7)	0.0351 (6)	−0.0021 (5)	−0.0036 (5)	0.0026 (5)
O1A	0.0400 (5)	0.0354 (5)	0.0342 (5)	−0.0092 (4)	−0.0105 (3)	0.0040 (4)
C1A	0.0319 (6)	0.0281 (6)	0.0257 (6)	−0.0012 (5)	−0.0023 (4)	0.0072 (4)
C2A	0.0324 (6)	0.0411 (7)	0.0297 (6)	0.0056 (5)	0.0043 (5)	0.0065 (5)
C3A	0.0468 (7)	0.0307 (6)	0.0236 (6)	0.0090 (5)	0.0033 (5)	−0.0016 (5)
C4A	0.0420 (7)	0.0206 (5)	0.0202 (5)	0.0009 (5)	−0.0029 (4)	0.0029 (4)
C5A	0.0568 (8)	0.0233 (6)	0.0219 (6)	−0.0028 (5)	−0.0059 (5)	−0.0013 (4)
C6A	0.0508 (8)	0.0282 (6)	0.0281 (6)	−0.0129 (6)	−0.0143 (5)	0.0037 (5)
C7A	0.0358 (7)	0.0281 (6)	0.0279 (6)	−0.0056 (5)	−0.0083 (5)	0.0104 (5)
C8A	0.0346 (7)	0.0413 (7)	0.0425 (7)	−0.0083 (6)	−0.0101 (5)	0.0161 (6)
C9A	0.0292 (6)	0.0506 (8)	0.0481 (8)	0.0017 (6)	0.0014 (5)	0.0206 (7)
C10A	0.0387 (7)	0.0384 (7)	0.0345 (6)	0.0106 (5)	0.0069 (5)	0.0104 (5)
C11A	0.0341 (6)	0.0257 (6)	0.0244 (5)	0.0044 (5)	−0.0002 (4)	0.0070 (4)
C12A	0.0430 (7)	0.0244 (6)	0.0239 (5)	0.0067 (5)	−0.0017 (5)	−0.0022 (4)
C13A	0.0383 (6)	0.0214 (6)	0.0257 (6)	−0.0009 (5)	−0.0080 (4)	−0.0012 (4)
C14A	0.0315 (6)	0.0197 (5)	0.0220 (5)	0.0001 (4)	−0.0032 (4)	0.0042 (4)
C15A	0.0330 (6)	0.0174 (5)	0.0190 (5)	0.0002 (4)	−0.0033 (4)	0.0036 (4)
C16A	0.0321 (6)	0.0205 (5)	0.0221 (5)	−0.0002 (4)	−0.0043 (4)	0.0072 (4)
C17A	0.0349 (6)	0.0411 (7)	0.0349 (7)	−0.0081 (6)	−0.0028 (5)	0.0093 (5)

O1—C17	1.4222 (14)	O1A—C17A	1.4301 (14)
O1—H1	0.8400	O1A—H1A	0.8400
C1—C2	1.3865 (15)	C1A—C2A	1.3922 (17)
C1—C14	1.4056 (15)	C1A—C14A	1.4094 (15)
C1—C17	1.5146 (15)	C1A—C17A	1.5000 (16)
C2—C3	1.3860 (17)	C2A—C3A	1.3824 (17)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C4	1.3887 (17)	C3A—C4A	1.3900 (16)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C15	1.4218 (15)	C4A—C15A	1.4232 (15)
C4—C5	1.4338 (16)	C4A—C5A	1.4334 (16)
C5—C6	1.3356 (19)	C5A—C6A	1.3415 (18)
C5—H5	0.9500	C5A—H5A	0.9500
C6—C7	1.434 (2)	C6A—C7A	1.4360 (17)
C6—H6	0.9500	C6A—H6A	0.9500
C7—C8	1.393 (2)	C7A—C8A	1.3971 (17)
C7—C16	1.4247 (16)	C7A—C16A	1.4233 (15)
C8—C9	1.377 (2)	C8A—C9A	1.383 (2)
C8—H8	0.9500	C8A—H8A	0.9500
C9—C10	1.386 (2)	C9A—C10A	1.3825 (19)
C9—H9	0.9500	C9A—H9A	0.9500
C10—C11	1.3969 (18)	C10A—C11A	1.3983 (16)
C10—H10	0.9500	C10A—H10A	0.9500
C11—C16	1.4187 (17)	C11A—C16A	1.4216 (15)
C11—C12	1.4295 (17)	C11A—C12A	1.4281 (16)
C12—C13	1.3459 (16)	C12A—C13A	1.3476 (16)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.4377 (15)	C13A—C14A	1.4371 (15)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.4246 (14)	C14A—C15A	1.4235 (14)
C15—C16	1.4201 (16)	C15A—C16A	1.4241 (15)
C17—H17A	0.9900	C17A—H17C	0.9900
C17—H17B	0.9900	C17A—H17D	0.9900
C17—O1—H1	109.5	C17A—O1A—H1A	109.5
C2—C1—C14	119.64 (10)	C2A—C1A—C14A	119.25 (10)
C2—C1—C17	121.08 (10)	C2A—C1A—C17A	118.94 (11)
C14—C1—C17	119.28 (10)	C14A—C1A—C17A	121.74 (11)
C3—C2—C1	121.36 (11)	C3A—C2A—C1A	121.82 (11)
C3—C2—H2	119.3	C3A—C2A—H2A	119.1
C1—C2—H2	119.3	C1A—C2A—H2A	119.1
C2—C3—C4	120.94 (10)	C2A—C3A—C4A	120.66 (11)
C2—C3—H3	119.5	C2A—C3A—H3A	119.7
C4—C3—H3	119.5	C4A—C3A—H3A	119.7
C3—C4—C15	118.84 (10)	C3A—C4A—C15A	118.95 (10)
C3—C4—C5	122.47 (11)	C3A—C4A—C5A	122.37 (10)
C15—C4—C5	118.69 (11)	C15A—C4A—C5A	118.68 (10)
C6—C5—C4	121.60 (12)	C6A—C5A—C4A	121.78 (11)
C6—C5—H5	119.2	C6A—C5A—H5A	119.1
C4—C5—H5	119.2	C4A—C5A—H5A	119.1
C5—C6—C7	121.51 (11)	C5A—C6A—C7A	121.40 (10)
C5—C6—H6	119.2	C5A—C6A—H6A	119.3
C7—C6—H6	119.2	C7A—C6A—H6A	119.3
C8—C7—C16	118.77 (13)	C8A—C7A—C16A	118.86 (11)
C8—C7—C6	122.73 (12)	C8A—C7A—C6A	122.87 (11)
C16—C7—C6	118.50 (12)	C16A—C7A—C6A	118.27 (11)
C9—C8—C7	121.00 (13)	C9A—C8A—C7A	121.06 (12)
C9—C8—H8	119.5	C9A—C8A—H8A	119.5
C7—C8—H8	119.5	C7A—C8A—H8A	119.5
C8—C9—C10	120.81 (13)	C10A—C9A—C8A	120.51 (12)
C8—C9—H9	119.6	C10A—C9A—H9A	119.7
C10—C9—H9	119.6	C8A—C9A—H9A	119.7
C9—C10—C11	120.59 (14)	C9A—C10A—C11A	120.82 (12)
C9—C10—H10	119.7	C9A—C10A—H10A	119.6
C11—C10—H10	119.7	C11A—C10A—H10A	119.6
C10—C11—C16	118.93 (12)	C10A—C11A—C16A	119.09 (11)
C10—C11—C12	122.74 (12)	C10A—C11A—C12A	122.55 (11)
C16—C11—C12	118.32 (10)	C16A—C11A—C12A	118.36 (10)
C13—C12—C11	121.68 (11)	C13A—C12A—C11A	121.88 (10)
C13—C12—H12	119.2	C13A—C12A—H12A	119.1
C11—C12—H12	119.2	C11A—C12A—H12A	119.1
C12—C13—C14	121.70 (10)	C12A—C13A—C14A	121.56 (10)
C12—C13—H13	119.2	C12A—C13A—H13A	119.2
C14—C13—H13	119.2	C14A—C13A—H13A	119.2
C1—C14—C15	119.25 (9)	C1A—C14A—C15A	119.19 (10)
C1—C14—C13	122.99 (10)	C1A—C14A—C13A	122.93 (10)
C15—C14—C13	117.76 (10)	C15A—C14A—C13A	117.87 (10)
C16—C15—C4	119.72 (10)	C4A—C15A—C14A	120.12 (10)
C16—C15—C14	120.31 (10)	C4A—C15A—C16A	119.43 (10)
C4—C15—C14	119.95 (10)	C14A—C15A—C16A	120.44 (9)
C11—C16—C15	120.17 (10)	C11A—C16A—C7A	119.67 (10)
C11—C16—C7	119.86 (11)	C11A—C16A—C15A	119.90 (10)
C15—C16—C7	119.96 (11)	C7A—C16A—C15A	120.43 (10)
O1—C17—C1	113.64 (10)	O1A—C17A—C1A	111.75 (9)
O1—C17—H17A	108.8	O1A—C17A—H17C	109.3
C1—C17—H17A	108.8	C1A—C17A—H17C	109.3
O1—C17—H17B	108.8	O1A—C17A—H17D	109.3
C1—C17—H17B	108.8	C1A—C17A—H17D	109.3
H17A—C17—H17B	107.7	H17C—C17A—H17D	107.9
C14—C1—C2—C3	−0.83 (16)	C14A—C1A—C2A—C3A	0.59 (17)
C17—C1—C2—C3	−179.82 (10)	C17A—C1A—C2A—C3A	−176.38 (10)
C1—C2—C3—C4	0.83 (17)	C1A—C2A—C3A—C4A	0.44 (18)
C2—C3—C4—C15	0.19 (16)	C2A—C3A—C4A—C15A	−0.83 (16)
C2—C3—C4—C5	179.32 (10)	C2A—C3A—C4A—C5A	179.05 (10)
C3—C4—C5—C6	−178.12 (11)	C3A—C4A—C5A—C6A	−178.71 (11)
C15—C4—C5—C6	1.01 (17)	C15A—C4A—C5A—C6A	1.17 (16)
C4—C5—C6—C7	0.19 (18)	C4A—C5A—C6A—C7A	−0.76 (17)
C5—C6—C7—C8	179.54 (12)	C5A—C6A—C7A—C8A	−179.58 (11)
C5—C6—C7—C16	−0.77 (18)	C5A—C6A—C7A—C16A	−0.22 (16)
C16—C7—C8—C9	1.55 (19)	C16A—C7A—C8A—C9A	0.14 (17)
C6—C7—C8—C9	−178.76 (13)	C6A—C7A—C8A—C9A	179.50 (11)
C7—C8—C9—C10	−1.0 (2)	C7A—C8A—C9A—C10A	−0.13 (18)
C8—C9—C10—C11	−0.6 (2)	C8A—C9A—C10A—C11A	0.17 (18)
C9—C10—C11—C16	1.65 (19)	C9A—C10A—C11A—C16A	−0.23 (16)
C9—C10—C11—C12	−177.77 (12)	C9A—C10A—C11A—C12A	179.31 (11)
C10—C11—C12—C13	−178.69 (11)	C10A—C11A—C12A—C13A	−179.03 (10)
C16—C11—C12—C13	1.88 (16)	C16A—C11A—C12A—C13A	0.50 (16)
C11—C12—C13—C14	0.14 (17)	C11A—C12A—C13A—C14A	−0.75 (17)
C2—C1—C14—C15	−0.18 (15)	C2A—C1A—C14A—C15A	−1.18 (15)
C17—C1—C14—C15	178.83 (9)	C17A—C1A—C14A—C15A	175.69 (9)
C2—C1—C14—C13	−179.59 (10)	C2A—C1A—C14A—C13A	179.92 (10)
C17—C1—C14—C13	−0.58 (15)	C17A—C1A—C14A—C13A	−3.20 (16)
C12—C13—C14—C1	177.38 (10)	C12A—C13A—C14A—C1A	179.07 (10)
C12—C13—C14—C15	−2.04 (15)	C12A—C13A—C14A—C15A	0.15 (15)
C3—C4—C15—C16	177.55 (9)	C3A—C4A—C15A—C14A	0.21 (15)
C5—C4—C15—C16	−1.62 (15)	C5A—C4A—C15A—C14A	−179.68 (9)
C3—C4—C15—C14	−1.19 (15)	C3A—C4A—C15A—C16A	179.28 (9)
C5—C4—C15—C14	179.65 (9)	C5A—C4A—C15A—C16A	−0.60 (14)
C1—C14—C15—C16	−177.54 (9)	C1A—C14A—C15A—C4A	0.80 (15)
C13—C14—C15—C16	1.90 (14)	C13A—C14A—C15A—C4A	179.75 (9)
C1—C14—C15—C4	1.18 (14)	C1A—C14A—C15A—C16A	−178.27 (9)
C13—C14—C15—C4	−179.38 (9)	C13A—C14A—C15A—C16A	0.68 (14)
C10—C11—C16—C15	178.59 (10)	C10A—C11A—C16A—C7A	0.24 (15)
C12—C11—C16—C15	−1.96 (15)	C12A—C11A—C16A—C7A	−179.32 (9)
C10—C11—C16—C7	−1.12 (16)	C10A—C11A—C16A—C15A	179.89 (9)
C12—C11—C16—C7	178.33 (10)	C12A—C11A—C16A—C15A	0.34 (15)
C4—C15—C16—C11	−178.65 (9)	C8A—C7A—C16A—C11A	−0.19 (15)
C14—C15—C16—C11	0.08 (15)	C6A—C7A—C16A—C11A	−179.58 (9)
C4—C15—C16—C7	1.05 (15)	C8A—C7A—C16A—C15A	−179.84 (9)
C14—C15—C16—C7	179.78 (9)	C6A—C7A—C16A—C15A	0.77 (15)
C8—C7—C16—C11	−0.46 (16)	C4A—C15A—C16A—C11A	180.00 (9)
C6—C7—C16—C11	179.84 (10)	C14A—C15A—C16A—C11A	−0.92 (15)
C8—C7—C16—C15	179.83 (10)	C4A—C15A—C16A—C7A	−0.35 (15)
C6—C7—C16—C15	0.13 (16)	C14A—C15A—C16A—C7A	178.73 (9)
C2—C1—C17—O1	−3.46 (15)	C2A—C1A—C17A—O1A	−116.54 (12)
C14—C1—C17—O1	177.53 (9)	C14A—C1A—C17A—O1A	66.57 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Ai	0.84	1.87	2.6972 (12)	167
O1A—H1A···O1ii	0.84	1.89	2.7163 (12)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1Ai	0.84	1.87	2.6972 (12)	167
O1A—H1A⋯O1ii	0.84	1.89	2.7163 (12)	167

Symmetry codes: (i) ; (ii) .