12,12'-[2,2'-Oxybis(ethane-2,1-di-yl)bis-(-oxy)]bis-[(R(p))-4-bromo-[2.2]paracyclo-phane].

The title compound, C(36)H(36)Br(2)O(3), was synthesized from (R(p))-4-bromo-12-hy-droxy[2.2]paracyclo-phane and oxydiethane-2,1-diyl bis-(4-methyl-benzene-sulfonate). The crystal packing exhibits a short O⋯Br inter-action [Br⋯O = 3.185 (3) Å] and a weak inter-molecular C-H⋯O contact.

Related literature

The title compound is an important inter­mediate in the application of paracyclo­phanes, especially used as ligands in asymmetric catalysis. For the structure of [2.2]paracyclo­phane, see: Singer & Cram (1963 ▶); Gibson & Knight (2003 ▶); Rivera et al. (2011 ▶). For bis­(diphenyl­phosphino)-[2.2]paracyclo­phane, see: Pye et al. (1997 ▶). For the application of salen ligands based on [2.2]paracyclo­phane as asymmetic ligands, see: Dahmen & Bräse (2002 ▶); Bräse & Höfener (2005 ▶); Lauterwasser et al. (2006 ▶). For the synthesis of (R p)-4-bromo-12-hy­droxy[2.2]paracyclo­phane, see: Jiang & Zhao (2004 ▶).

Experimental

Crystal data

C36H36Br2O3

M = 676.47

Orthorhombic,

a = 8.850 (4) Å

b = 12.019 (5) Å

c = 28.242 (12) Å

V = 3004 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.73 mm−1

T = 273 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.718, T max = 0.772

12887 measured reflections

4331 independent reflections

3692 reflections with I > 2σ(I)

R int = 0.030

θmax = 23.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.068

S = 1.02

4331 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1839 Friedel pairs

Flack parameter: 0.008 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010051/fy2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010051/fy2003Isup2.hkl

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

C36H36Br2O3	F(000) = 1384
Mr = 676.47	Dx = 1.496 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4449 reflections
a = 8.850 (4) Å	θ = 1.8–23.3°
b = 12.019 (5) Å	µ = 2.73 mm−1
c = 28.242 (12) Å	T = 273 K
V = 3004 (2) Å3	Block, colourless
Z = 4	0.13 × 0.12 × 0.10 mm

Bruker APEXII CCD diffractometer	4331 independent reflections
Radiation source: fine-focus sealed tube	3692 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 23.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→7
Tmin = 0.718, Tmax = 0.772	k = −13→13
12887 measured reflections	l = −29→31

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0252P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4331 reflections	Δρmax = 0.39 e Å−3
370 parameters	Δρmin = −0.35 e Å−3
0 restraints	Absolute structure: Flack (1983), 1839 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.008 (8)

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.

	x	y	z	Uiso*/Ueq
C36	0.8319 (4)	0.9667 (3)	0.15546 (12)	0.0480 (10)
C37	0.7036 (5)	0.9418 (3)	0.12979 (13)	0.0504 (9)
H37	0.6686	0.8689	0.1285	0.060*
Br1	0.30618 (5)	0.68396 (4)	0.081628 (14)	0.06634 (15)
Br2	0.94686 (6)	0.84669 (4)	0.180636 (15)	0.07790 (17)
O3	0.8123 (3)	0.85002 (19)	0.03021 (8)	0.0485 (6)
O2	0.8426 (3)	0.56317 (18)	0.05928 (8)	0.0462 (6)
O1	0.6407 (3)	0.4291 (2)	0.11810 (8)	0.0476 (6)
C20	0.7812 (4)	0.6565 (3)	0.03631 (12)	0.0462 (9)
H20A	0.6803	0.6718	0.0480	0.055*
H20B	0.7758	0.6439	0.0024	0.055*
C32	0.7909 (5)	1.1572 (3)	0.14345 (13)	0.0608 (11)
H32	0.8128	1.2307	0.1511	0.073*
C1	0.3373 (4)	0.6550 (3)	0.14721 (12)	0.0445 (9)
C22	0.8814 (4)	0.9506 (3)	0.03838 (12)	0.0409 (9)
C19	0.7751 (4)	0.4601 (3)	0.04702 (14)	0.0482 (9)
H19A	0.8415	0.4003	0.0571	0.058*
H19B	0.7664	0.4560	0.0128	0.058*
C21	0.8846 (4)	0.7518 (3)	0.04703 (13)	0.0446 (9)
H21A	0.9023	0.7570	0.0809	0.054*
H21B	0.9810	0.7415	0.0313	0.054*
C5	0.2497 (5)	0.6113 (3)	0.22280 (14)	0.0529 (10)
H5	0.1702	0.6053	0.2442	0.064*
C6	0.2185 (4)	0.6201 (3)	0.17485 (13)	0.0431 (9)
C13	0.2424 (4)	0.3949 (3)	0.15319 (14)	0.0470 (10)
C27	0.7969 (5)	1.0433 (3)	0.02457 (12)	0.0493 (10)
C33	0.8887 (4)	1.0734 (3)	0.15801 (12)	0.0520 (10)
C14	0.3689 (4)	0.4055 (3)	0.12492 (13)	0.0437 (9)
H14	0.3573	0.4127	0.0923	0.052*
C15	0.5121 (4)	0.4056 (2)	0.14417 (12)	0.0377 (8)
C3	0.5171 (4)	0.6198 (3)	0.20919 (14)	0.0495 (10)
C2	0.4856 (4)	0.6531 (3)	0.16317 (13)	0.0474 (9)
H2	0.5637	0.6741	0.1431	0.057*
C31	0.6617 (5)	1.1336 (3)	0.11786 (15)	0.0604 (11)
H31	0.5979	1.1910	0.1086	0.072*
C24	1.0629 (4)	1.0686 (3)	0.07684 (14)	0.0545 (10)
C30	0.6268 (4)	1.0250 (3)	0.10591 (14)	0.0523 (10)
C10	0.5332 (4)	0.3950 (3)	0.19276 (13)	0.0463 (9)
C12	0.2648 (5)	0.3616 (3)	0.19911 (15)	0.0576 (11)
H12	0.1831	0.3380	0.2172	0.069*
C18	0.6230 (4)	0.4419 (3)	0.06822 (12)	0.0457 (9)
H18A	0.5580	0.5049	0.0615	0.055*
H18B	0.5770	0.3757	0.0548	0.055*
C26	0.8660 (5)	1.1451 (3)	0.02910 (14)	0.0617 (11)
H26	0.8225	1.2067	0.0146	0.074*
C25	0.9965 (5)	1.1587 (3)	0.05427 (15)	0.0631 (12)
H25	1.0411	1.2286	0.0563	0.076*
C23	1.0121 (4)	0.9619 (3)	0.06396 (13)	0.0447 (9)
H23	1.0669	0.8993	0.0728	0.054*
C4	0.3970 (5)	0.6113 (3)	0.23964 (14)	0.0573 (11)
H4	0.4145	0.6054	0.2720	0.069*
C34	1.0530 (5)	1.1017 (4)	0.16609 (16)	0.0777 (13)
H34A	1.0907	1.0575	0.1923	0.093*
H34B	1.0607	1.1794	0.1750	0.093*
C9	0.6714 (5)	0.4413 (3)	0.21679 (14)	0.0637 (11)
H9A	0.7605	0.4190	0.1992	0.076*
H9B	0.6792	0.4098	0.2483	0.076*
C28	0.6283 (5)	1.0321 (3)	0.01627 (15)	0.0649 (12)
H28A	0.6112	0.9766	−0.0081	0.078*
H28B	0.5893	1.1024	0.0047	0.078*
C17	0.0757 (4)	0.5687 (3)	0.15545 (15)	0.0569 (10)
H17A	0.0389	0.6144	0.1296	0.068*
H17B	−0.0007	0.5688	0.1801	0.068*
C35	1.1557 (4)	1.0805 (4)	0.12142 (17)	0.0720 (13)
H35A	1.2257	1.1420	0.1178	0.086*
H35B	1.2144	1.0132	0.1263	0.086*
C8	0.6679 (5)	0.5712 (4)	0.22061 (18)	0.0763 (13)
H8A	0.6958	0.5927	0.2525	0.092*
H8B	0.7426	0.6021	0.1992	0.092*
C11	0.4078 (5)	0.3627 (3)	0.21874 (14)	0.0540 (10)
H11	0.4202	0.3413	0.2501	0.065*
C29	0.5392 (5)	0.9983 (4)	0.06158 (16)	0.0708 (12)
H29A	0.4434	1.0376	0.0622	0.085*
H29B	0.5179	0.9192	0.0606	0.085*
C16	0.0974 (4)	0.4463 (3)	0.13707 (16)	0.0604 (11)
H16A	0.0138	0.4011	0.1481	0.073*
H16B	0.0948	0.4465	0.1027	0.073*

	U11	U22	U33	U12	U13	U23
C36	0.067 (3)	0.041 (2)	0.035 (2)	0.0044 (19)	0.0096 (19)	−0.0025 (16)
C37	0.061 (3)	0.045 (2)	0.045 (2)	−0.008 (2)	0.015 (2)	−0.0008 (18)
Br1	0.0764 (3)	0.0724 (3)	0.0503 (2)	0.0140 (2)	0.0005 (2)	0.0209 (2)
Br2	0.1185 (4)	0.0657 (3)	0.0495 (2)	0.0250 (3)	−0.0064 (2)	0.0065 (2)
O3	0.0626 (15)	0.0360 (14)	0.0469 (14)	0.0062 (13)	−0.0120 (12)	−0.0028 (11)
O2	0.0512 (15)	0.0357 (13)	0.0518 (15)	0.0001 (11)	−0.0107 (11)	0.0038 (11)
O1	0.0444 (15)	0.0576 (16)	0.0408 (15)	0.0075 (12)	−0.0015 (11)	0.0014 (12)
C20	0.050 (2)	0.041 (2)	0.047 (2)	0.0013 (18)	−0.0043 (17)	0.0023 (17)
C32	0.093 (3)	0.041 (2)	0.048 (2)	0.003 (3)	0.020 (2)	−0.0084 (19)
C1	0.057 (3)	0.0297 (19)	0.046 (2)	0.0067 (17)	0.0024 (18)	−0.0007 (16)
C22	0.062 (2)	0.032 (2)	0.0288 (19)	−0.0007 (17)	0.0063 (17)	−0.0032 (15)
C19	0.051 (2)	0.043 (2)	0.051 (2)	0.0000 (17)	0.0003 (18)	−0.0058 (17)
C21	0.055 (2)	0.036 (2)	0.043 (2)	0.0076 (17)	−0.0055 (18)	−0.0001 (16)
C5	0.064 (3)	0.053 (2)	0.042 (2)	0.0063 (18)	0.0116 (19)	−0.0043 (18)
C6	0.041 (2)	0.0379 (19)	0.051 (2)	0.0099 (16)	0.0042 (19)	−0.0009 (16)
C13	0.044 (2)	0.037 (2)	0.059 (3)	−0.0099 (16)	0.0070 (19)	−0.0029 (18)
C27	0.082 (3)	0.032 (2)	0.034 (2)	0.007 (2)	0.005 (2)	0.0003 (15)
C33	0.064 (3)	0.055 (3)	0.036 (2)	−0.002 (2)	0.0006 (18)	−0.0110 (17)
C14	0.053 (2)	0.030 (2)	0.048 (2)	−0.0042 (16)	−0.0032 (19)	−0.0041 (16)
C15	0.043 (2)	0.0244 (18)	0.046 (2)	0.0044 (15)	0.0017 (17)	0.0036 (15)
C3	0.048 (3)	0.043 (2)	0.057 (3)	−0.0039 (17)	−0.011 (2)	−0.0122 (17)
C2	0.046 (2)	0.040 (2)	0.056 (2)	−0.0076 (17)	0.0028 (18)	−0.0023 (18)
C31	0.073 (3)	0.054 (3)	0.054 (3)	0.023 (2)	0.012 (2)	−0.003 (2)
C24	0.052 (2)	0.051 (2)	0.060 (3)	−0.0082 (19)	0.018 (2)	−0.008 (2)
C30	0.050 (2)	0.051 (3)	0.056 (3)	0.0055 (19)	0.0150 (19)	−0.005 (2)
C10	0.054 (2)	0.0371 (19)	0.048 (2)	0.0125 (17)	−0.004 (2)	0.0043 (16)
C12	0.064 (3)	0.044 (2)	0.065 (3)	−0.0105 (19)	0.019 (2)	0.003 (2)
C18	0.046 (2)	0.047 (2)	0.044 (2)	−0.0029 (17)	−0.0041 (17)	−0.0017 (17)
C26	0.101 (4)	0.043 (3)	0.041 (2)	0.002 (2)	0.011 (2)	0.0051 (19)
C25	0.090 (3)	0.034 (2)	0.066 (3)	−0.019 (2)	0.031 (2)	−0.002 (2)
C23	0.048 (2)	0.040 (2)	0.046 (2)	0.0025 (16)	0.0140 (18)	−0.0039 (16)
C4	0.075 (3)	0.056 (3)	0.041 (2)	0.005 (2)	−0.008 (2)	−0.0141 (18)
C34	0.087 (3)	0.076 (3)	0.070 (3)	−0.012 (3)	−0.012 (3)	−0.023 (2)
C9	0.067 (3)	0.078 (3)	0.046 (2)	0.023 (2)	−0.015 (2)	0.004 (2)
C28	0.081 (3)	0.052 (3)	0.062 (3)	0.019 (2)	−0.023 (2)	0.001 (2)
C17	0.039 (2)	0.066 (3)	0.066 (3)	0.0039 (19)	0.0009 (19)	0.000 (2)
C35	0.052 (3)	0.072 (3)	0.091 (4)	−0.011 (2)	−0.001 (2)	−0.023 (3)
C8	0.055 (3)	0.092 (4)	0.082 (3)	−0.009 (3)	−0.028 (2)	−0.007 (3)
C11	0.080 (3)	0.036 (2)	0.046 (2)	0.007 (2)	0.003 (2)	0.0136 (17)
C29	0.057 (3)	0.075 (3)	0.080 (3)	0.015 (2)	−0.011 (2)	−0.010 (2)
C16	0.043 (2)	0.063 (3)	0.075 (3)	−0.015 (2)	0.000 (2)	−0.005 (2)

C36—C33	1.380 (5)	C3—C2	1.388 (5)
C36—C37	1.380 (5)	C3—C8	1.492 (5)
C36—Br2	1.903 (4)	C2—H2	0.9300
C37—C30	1.384 (5)	C31—C30	1.383 (5)
C37—H37	0.9300	C31—H31	0.9300
Br1—C1	1.905 (3)	C24—C25	1.387 (6)
O3—C22	1.374 (4)	C24—C23	1.407 (5)
O3—C21	1.424 (4)	C24—C35	1.510 (6)
O2—C20	1.405 (4)	C30—C29	1.507 (6)
O2—C19	1.418 (4)	C10—C11	1.386 (5)
O1—C15	1.385 (4)	C10—C9	1.506 (5)
O1—C18	1.426 (4)	C12—C11	1.381 (6)
C20—C21	1.497 (5)	C12—H12	0.9300
C20—H20A	0.9700	C18—H18A	0.9700
C20—H20B	0.9700	C18—H18B	0.9700
C32—C31	1.382 (6)	C26—C25	1.366 (6)
C32—C33	1.390 (6)	C26—H26	0.9300
C32—H32	0.9300	C25—H25	0.9300
C1—C6	1.375 (5)	C23—H23	0.9300
C1—C2	1.387 (5)	C4—H4	0.9300
C22—C23	1.370 (5)	C34—C35	1.576 (6)
C22—C27	1.397 (5)	C34—H34A	0.9700
C19—C18	1.490 (5)	C34—H34B	0.9700
C19—H19A	0.9700	C9—C8	1.565 (6)
C19—H19B	0.9700	C9—H9A	0.9700
C21—H21A	0.9700	C9—H9B	0.9700
C21—H21B	0.9700	C28—C29	1.557 (6)
C5—C6	1.386 (5)	C28—H28A	0.9700
C5—C4	1.387 (5)	C28—H28B	0.9700
C5—H5	0.9300	C17—C16	1.572 (5)
C6—C17	1.509 (5)	C17—H17A	0.9700
C13—C12	1.372 (5)	C17—H17B	0.9700
C13—C14	1.381 (5)	C35—H35A	0.9700
C13—C16	1.495 (5)	C35—H35B	0.9700
C27—C26	1.373 (5)	C8—H8A	0.9700
C27—C28	1.517 (6)	C8—H8B	0.9700
C33—C34	1.510 (6)	C11—H11	0.9300
C14—C15	1.379 (5)	C29—H29A	0.9700
C14—H14	0.9300	C29—H29B	0.9700
C15—C10	1.391 (5)	C16—H16A	0.9700
C3—C4	1.372 (5)	C16—H16B	0.9700
C33—C36—C37	121.9 (3)	C15—C10—C9	121.3 (3)
C33—C36—Br2	119.4 (3)	C13—C12—C11	120.6 (3)
C37—C36—Br2	118.2 (3)	C13—C12—H12	119.7
C36—C37—C30	120.3 (3)	C11—C12—H12	119.7
C36—C37—H37	119.9	O1—C18—C19	108.3 (3)
C30—C37—H37	119.9	O1—C18—H18A	110.0
C22—O3—C21	118.3 (3)	C19—C18—H18A	110.0
C20—O2—C19	115.0 (3)	O1—C18—H18B	110.0
C15—O1—C18	117.2 (3)	C19—C18—H18B	110.0
O2—C20—C21	106.4 (3)	H18A—C18—H18B	108.4
O2—C20—H20A	110.5	C25—C26—C27	122.1 (4)
C21—C20—H20A	110.5	C25—C26—H26	118.9
O2—C20—H20B	110.5	C27—C26—H26	118.9
C21—C20—H20B	110.5	C26—C25—C24	120.3 (4)
H20A—C20—H20B	108.6	C26—C25—H25	119.9
C31—C32—C33	121.4 (4)	C24—C25—H25	119.9
C31—C32—H32	119.3	C22—C23—C24	119.8 (4)
C33—C32—H32	119.3	C22—C23—H23	120.1
C6—C1—C2	122.2 (3)	C24—C23—H23	120.1
C6—C1—Br1	119.8 (3)	C3—C4—C5	120.9 (4)
C2—C1—Br1	117.1 (3)	C3—C4—H4	119.6
C23—C22—O3	123.4 (3)	C5—C4—H4	119.6
C23—C22—C27	121.3 (3)	C33—C34—C35	113.5 (3)
O3—C22—C27	114.6 (3)	C33—C34—H34A	108.9
O2—C19—C18	114.2 (3)	C35—C34—H34A	108.9
O2—C19—H19A	108.7	C33—C34—H34B	108.9
C18—C19—H19A	108.7	C35—C34—H34B	108.9
O2—C19—H19B	108.7	H34A—C34—H34B	107.7
C18—C19—H19B	108.7	C10—C9—C8	112.5 (3)
H19A—C19—H19B	107.6	C10—C9—H9A	109.1
O3—C21—C20	107.0 (3)	C8—C9—H9A	109.1
O3—C21—H21A	110.3	C10—C9—H9B	109.1
C20—C21—H21A	110.3	C8—C9—H9B	109.1
O3—C21—H21B	110.3	H9A—C9—H9B	107.8
C20—C21—H21B	110.3	C27—C28—C29	113.2 (3)
H21A—C21—H21B	108.6	C27—C28—H28A	108.9
C6—C5—C4	121.5 (4)	C29—C28—H28A	108.9
C6—C5—H5	119.3	C27—C28—H28B	108.9
C4—C5—H5	119.3	C29—C28—H28B	108.9
C1—C6—C5	115.2 (3)	H28A—C28—H28B	107.7
C1—C6—C17	124.0 (3)	C6—C17—C16	113.6 (3)
C5—C6—C17	119.4 (3)	C6—C17—H17A	108.8
C12—C13—C14	117.2 (4)	C16—C17—H17A	108.8
C12—C13—C16	122.2 (4)	C6—C17—H17B	108.8
C14—C13—C16	118.8 (3)	C16—C17—H17B	108.8
C26—C27—C22	116.5 (4)	H17A—C17—H17B	107.7
C26—C27—C28	122.1 (4)	C24—C35—C34	111.6 (3)
C22—C27—C28	119.9 (3)	C24—C35—H35A	109.3
C36—C33—C32	115.5 (4)	C34—C35—H35A	109.3
C36—C33—C34	124.6 (4)	C24—C35—H35B	109.3
C32—C33—C34	118.8 (4)	C34—C35—H35B	109.3
C15—C14—C13	121.1 (3)	H35A—C35—H35B	108.0
C15—C14—H14	119.4	C3—C8—C9	113.2 (3)
C13—C14—H14	119.4	C3—C8—H8A	108.9
C14—C15—O1	123.1 (3)	C9—C8—H8A	108.9
C14—C15—C10	120.8 (3)	C3—C8—H8B	108.9
O1—C15—C10	115.6 (3)	C9—C8—H8B	108.9
C4—C3—C2	116.9 (3)	H8A—C8—H8B	107.7
C4—C3—C8	121.9 (4)	C12—C11—C10	121.6 (4)
C2—C3—C8	119.7 (4)	C12—C11—H11	119.2
C1—C2—C3	120.0 (3)	C10—C11—H11	119.2
C1—C2—H2	120.0	C30—C29—C28	111.5 (3)
C3—C2—H2	120.0	C30—C29—H29A	109.3
C32—C31—C30	120.4 (4)	C28—C29—H29A	109.3
C32—C31—H31	119.8	C30—C29—H29B	109.3
C30—C31—H31	119.8	C28—C29—H29B	109.3
C25—C24—C23	117.2 (4)	H29A—C29—H29B	108.0
C25—C24—C35	122.7 (4)	C13—C16—C17	113.0 (3)
C23—C24—C35	118.4 (4)	C13—C16—H16A	109.0
C31—C30—C37	116.9 (4)	C17—C16—H16A	109.0
C31—C30—C29	121.2 (4)	C13—C16—H16B	109.0
C37—C30—C29	120.3 (4)	C17—C16—H16B	109.0
C11—C10—C15	116.1 (3)	H16A—C16—H16B	107.8
C11—C10—C9	121.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O2i	0.97	2.71	3.412 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O2i	0.97	2.71	3.412 (5)	130

Symmetry code: (i) .