2,4-Dimethyl-6-phenyl-8-oxabicyclo­[3.2.1]octan-3-one

Dockendorff, C.; Lautens, M.; Lough, A.J.

doi:10.1107/S1600536806009779

Buy article online - an online subscription or single-article purchase is required to access this article.

2,4-Dimethyl-6-phenyl-8-oxabicyclo[3.2.1]octan-3-one

C. Dockendorff, M. Lautens and A. J. Lough

The asymmetric unit of the title crystal structure, C₁₅H₁₈O₂, contains two independent molecules which have essentially the same conformation. Two independent one-dimensional chains are formed via weak C—H

O hydrogen bonds. A further single weak C—H

O interaction links the two types of chain, forming extended tapes running in the a-axis direction.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009779/bv2009sup1.cif Contains datablocks global, 2
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009779/bv20092sup2.hkl Contains datablock 2

CCDC reference: 605001

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.129
Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.743     0.988
            Tmin(prime) and Tmax expected:      0.978     0.987
            RR(prime) =      0.758
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         26

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               3223
           Count of symmetry unique reflns         3324
           Completeness (_total/calc)             96.96%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,4-Dimethyl-6-phenyl-8-oxabicyclo[3.2.1]octan-3-one top

Crystal data top

C₁₅H₁₈O₂	F(000) = 992
M_r = 230.29	D_x = 1.217 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10473 reflections
a = 5.5808 (3) Å	θ = 2.7–27.5°
b = 14.8272 (6) Å	µ = 0.08 mm⁻¹
c = 30.3806 (17) Å	T = 150 K
V = 2513.9 (2) Å³	Plate, colourless
Z = 8	0.27 × 0.20 × 0.17 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	3223 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
φ scans and ω scans with κ offsets	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −16→18
T_min = 0.743, T_max = 0.988	l = −39→39
10473 measured reflections

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
3223 reflections	(Δ/σ)_max < 0.001
311 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

Experimental. ¹H NMR (400 MHz, CDCl₃): δ 7.34–7.17 (5H, m), 4.67 (1H, dd, J = 7.0, 4.4 Hz), 4.37 (1H, d, J = 4.8 Hz), 3.01 (1H, dd, J = 9.2, 5.5 Hz), 2.90–2.81 (2H, m), 2.27 (1H, dd, J = 13.2, 9.2 Hz), 1.92 (1H, m), 1.04 (3H, d, J = 7.0 Hz), 1.00 (3H, d, J = 7.0 Hz).

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.5904 (4)	0.64320 (15)	0.42742 (6)	0.0470 (6)
O2A	0.0760 (5)	0.69376 (18)	0.33815 (7)	0.0645 (7)
C1A	0.4763 (6)	0.7302 (2)	0.42486 (10)	0.0477 (9)
H1AA	0.5824	0.7780	0.4375	0.057*
C2A	0.4209 (7)	0.7501 (2)	0.37611 (10)	0.0497 (9)
H2AA	0.5752	0.7460	0.3595	0.060*
C3A	0.2585 (6)	0.6779 (2)	0.35874 (9)	0.0451 (8)
C4A	0.3328 (7)	0.5825 (2)	0.37036 (9)	0.0460 (9)
H4AA	0.4823	0.5686	0.3535	0.055*
C5A	0.3977 (6)	0.5820 (2)	0.41987 (9)	0.0410 (8)
H5AA	0.4460	0.5198	0.4290	0.049*
C6A	0.1927 (6)	0.61609 (19)	0.44962 (9)	0.0371 (7)
H6AA	0.0367	0.6088	0.4338	0.045*
C7A	0.2530 (6)	0.7176 (2)	0.45326 (9)	0.0464 (9)
H7AA	0.1190	0.7549	0.4421	0.056*
H7AB	0.2857	0.7346	0.4842	0.056*
C8A	0.3219 (9)	0.8455 (2)	0.36950 (11)	0.0755 (13)
H8AA	0.3041	0.8576	0.3380	0.113*
H8AB	0.4330	0.8894	0.3824	0.113*
H8AC	0.1655	0.8506	0.3839	0.113*
C9A	0.1487 (9)	0.5107 (3)	0.35875 (10)	0.0771 (14)
H9AA	0.1359	0.5056	0.3267	0.116*
H9AB	−0.0073	0.5275	0.3711	0.116*
H9AC	0.1991	0.4526	0.3710	0.116*
C10A	0.1828 (5)	0.5648 (2)	0.49235 (9)	0.0366 (7)
C11A	−0.0091 (5)	0.5074 (2)	0.50117 (10)	0.0440 (8)
H11A	−0.1412	0.5057	0.4815	0.053*
C12A	−0.0104 (6)	0.4524 (2)	0.53841 (11)	0.0494 (9)
H12A	−0.1419	0.4132	0.5438	0.059*
C13A	0.1771 (7)	0.4550 (2)	0.56716 (11)	0.0482 (9)
H13A	0.1759	0.4175	0.5925	0.058*
C14A	0.3684 (6)	0.5117 (2)	0.55955 (10)	0.0471 (9)
H14A	0.4983	0.5136	0.5798	0.056*
C15A	0.3712 (6)	0.5663 (2)	0.52218 (9)	0.0404 (8)
H15A	0.5038	0.6051	0.5171	0.048*
O1B	−0.0779 (4)	0.17182 (14)	0.31513 (7)	0.0461 (6)
O2B	0.4266 (5)	0.13061 (18)	0.22345 (8)	0.0658 (7)
C1B	0.0398 (6)	0.0856 (2)	0.31013 (10)	0.0458 (9)
H1BA	−0.0623	0.0364	0.3226	0.055*
C2B	0.0879 (7)	0.0686 (2)	0.26100 (10)	0.0481 (8)
H2BA	−0.0688	0.0720	0.2451	0.058*
C3B	0.2439 (6)	0.1436 (2)	0.24430 (10)	0.0464 (8)
C4B	0.1647 (6)	0.2375 (2)	0.25749 (9)	0.0442 (8)
H4BA	0.0115	0.2511	0.2418	0.053*
C5B	0.1114 (6)	0.2348 (2)	0.30720 (9)	0.0382 (7)
H5BA	0.0640	0.2961	0.3178	0.046*
C6B	0.3271 (6)	0.1991 (2)	0.33430 (9)	0.0366 (7)
H6BA	0.4772	0.2066	0.3167	0.044*
C7B	0.2662 (6)	0.0972 (2)	0.33769 (10)	0.0462 (9)
H7BA	0.3985	0.0600	0.3258	0.055*
H7BB	0.2368	0.0797	0.3687	0.055*
C8B	0.1943 (8)	−0.0245 (2)	0.25278 (11)	0.0679 (11)
H8BA	0.2052	−0.0353	0.2210	0.102*
H8BB	0.0915	−0.0704	0.2662	0.102*
H8BC	0.3548	−0.0277	0.2658	0.102*
C9B	0.3451 (8)	0.3104 (2)	0.24558 (11)	0.0701 (12)
H9BA	0.3485	0.3183	0.2136	0.105*
H9BB	0.5045	0.2927	0.2559	0.105*
H9BC	0.2985	0.3674	0.2596	0.105*
C10B	0.3565 (5)	0.24644 (19)	0.37810 (9)	0.0354 (7)
C11B	0.5629 (6)	0.2956 (2)	0.38637 (10)	0.0435 (8)
H11B	0.6848	0.2986	0.3646	0.052*
C12B	0.5937 (7)	0.3407 (2)	0.42604 (11)	0.0528 (9)
H12B	0.7362	0.3740	0.4313	0.063*
C13B	0.4177 (7)	0.3370 (2)	0.45780 (10)	0.0467 (9)
H13B	0.4387	0.3678	0.4849	0.056*
C14B	0.2117 (7)	0.2887 (2)	0.45014 (10)	0.0465 (8)
H14B	0.0900	0.2863	0.4720	0.056*
C15B	0.1813 (6)	0.2435 (2)	0.41045 (9)	0.0420 (8)
H15B	0.0386	0.2101	0.4054	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0343 (12)	0.0633 (15)	0.0433 (12)	0.0022 (12)	−0.0034 (11)	0.0068 (11)
O2A	0.0638 (16)	0.0845 (18)	0.0453 (13)	0.0135 (16)	−0.0131 (14)	0.0077 (13)
C1A	0.057 (2)	0.047 (2)	0.0392 (17)	−0.0054 (18)	0.0003 (17)	0.0019 (16)
C2A	0.060 (2)	0.050 (2)	0.0390 (17)	0.001 (2)	0.0032 (18)	0.0056 (16)
C3A	0.049 (2)	0.058 (2)	0.0285 (15)	0.0094 (19)	0.0020 (16)	0.0032 (15)
C4A	0.060 (2)	0.047 (2)	0.0311 (15)	0.0045 (18)	−0.0006 (17)	−0.0004 (15)
C5A	0.0423 (19)	0.0429 (18)	0.0376 (16)	0.0052 (16)	0.0021 (16)	0.0018 (15)
C6A	0.0328 (17)	0.0458 (19)	0.0328 (15)	0.0027 (15)	−0.0029 (14)	0.0008 (14)
C7A	0.060 (2)	0.044 (2)	0.0347 (16)	0.0097 (18)	0.0037 (17)	0.0010 (15)
C8A	0.123 (4)	0.051 (2)	0.053 (2)	0.010 (3)	0.008 (3)	0.0117 (19)
C9A	0.119 (4)	0.070 (3)	0.042 (2)	−0.012 (3)	−0.022 (2)	−0.0060 (19)
C10A	0.0341 (17)	0.0435 (18)	0.0322 (15)	0.0041 (16)	0.0002 (14)	−0.0039 (14)
C11A	0.0370 (18)	0.053 (2)	0.0416 (17)	−0.0005 (16)	0.0012 (15)	−0.0045 (18)
C12A	0.045 (2)	0.052 (2)	0.0505 (19)	−0.0088 (17)	0.0114 (18)	−0.0002 (18)
C13A	0.055 (2)	0.048 (2)	0.0415 (17)	0.0028 (19)	0.0091 (18)	0.0081 (16)
C14A	0.047 (2)	0.056 (2)	0.0387 (17)	0.0019 (19)	−0.0054 (16)	0.0060 (17)
C15A	0.0361 (18)	0.0465 (19)	0.0387 (16)	−0.0026 (16)	−0.0014 (15)	0.0003 (15)
O1B	0.0316 (11)	0.0568 (14)	0.0499 (12)	−0.0016 (11)	0.0008 (11)	−0.0068 (11)
O2B	0.0615 (16)	0.0849 (18)	0.0509 (14)	0.0163 (16)	0.0140 (15)	−0.0077 (13)
C1B	0.044 (2)	0.047 (2)	0.0457 (18)	−0.0057 (17)	−0.0013 (17)	−0.0008 (16)
C2B	0.048 (2)	0.050 (2)	0.0466 (18)	0.0037 (19)	−0.0092 (18)	−0.0095 (17)
C3B	0.044 (2)	0.062 (2)	0.0337 (16)	0.0114 (19)	−0.0032 (17)	−0.0049 (17)
C4B	0.0488 (19)	0.0502 (19)	0.0335 (15)	0.0049 (17)	−0.0026 (16)	0.0014 (15)
C5B	0.0360 (17)	0.0441 (18)	0.0344 (15)	0.0050 (15)	−0.0005 (14)	−0.0016 (14)
C6B	0.0331 (16)	0.0397 (17)	0.0371 (16)	0.0014 (15)	−0.0008 (15)	−0.0043 (14)
C7B	0.053 (2)	0.044 (2)	0.0414 (17)	0.0066 (17)	−0.0069 (18)	−0.0019 (15)
C8B	0.092 (3)	0.056 (2)	0.057 (2)	0.011 (2)	−0.018 (2)	−0.0155 (18)
C9B	0.099 (3)	0.066 (2)	0.0459 (19)	−0.012 (2)	0.014 (2)	0.0098 (19)
C10B	0.0331 (17)	0.0396 (18)	0.0334 (15)	0.0024 (15)	−0.0025 (14)	−0.0017 (14)
C11B	0.0363 (18)	0.048 (2)	0.0458 (18)	0.0023 (17)	−0.0027 (16)	−0.0092 (16)
C12B	0.043 (2)	0.054 (2)	0.062 (2)	0.0061 (18)	−0.0077 (19)	−0.0130 (18)
C13B	0.057 (2)	0.044 (2)	0.0396 (17)	0.012 (2)	−0.0144 (19)	−0.0071 (16)
C14B	0.054 (2)	0.051 (2)	0.0339 (16)	0.0072 (19)	0.0017 (16)	0.0035 (16)
C15B	0.0428 (18)	0.0460 (19)	0.0372 (16)	0.0024 (17)	0.0007 (15)	0.0017 (15)

Geometric parameters (Å, º) top

O1A—C5A	1.426 (4)	O1B—C5B	1.430 (4)
O1A—C1A	1.440 (4)	O1B—C1B	1.446 (4)
O2A—C3A	1.218 (4)	O2B—C3B	1.216 (4)
C1A—C7A	1.527 (4)	C1B—C7B	1.525 (4)
C1A—C2A	1.542 (4)	C1B—C2B	1.537 (4)
C1A—H1AA	1.0000	C1B—H1BA	1.0000
C2A—C3A	1.498 (5)	C2B—C3B	1.501 (5)
C2A—C8A	1.532 (5)	C2B—C8B	1.524 (5)
C2A—H2AA	1.0000	C2B—H2BA	1.0000
C3A—C4A	1.516 (4)	C3B—C4B	1.515 (4)
C4A—C9A	1.521 (5)	C4B—C9B	1.521 (4)
C4A—C5A	1.547 (4)	C4B—C5B	1.540 (4)
C4A—H4AA	1.0000	C4B—H4BA	1.0000
C5A—C6A	1.543 (4)	C5B—C6B	1.552 (4)
C5A—H5AA	1.0000	C5B—H5BA	1.0000
C6A—C10A	1.506 (4)	C6B—C10B	1.513 (4)
C6A—C7A	1.547 (4)	C6B—C7B	1.552 (4)
C6A—H6AA	1.0000	C6B—H6BA	1.0000
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C10A—C15A	1.388 (4)	C10B—C11B	1.386 (4)
C10A—C11A	1.394 (4)	C10B—C15B	1.387 (4)
C11A—C12A	1.394 (4)	C11B—C12B	1.389 (4)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.364 (5)	C12B—C13B	1.378 (5)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.379 (4)	C13B—C14B	1.374 (5)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.394 (4)	C14B—C15B	1.390 (4)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500

C5A—O1A—C1A	103.2 (2)	C5B—O1B—C1B	102.9 (2)
O1A—C1A—C7A	102.8 (2)	O1B—C1B—C7B	102.6 (2)
O1A—C1A—C2A	108.2 (3)	O1B—C1B—C2B	109.0 (3)
C7A—C1A—C2A	113.7 (3)	C7B—C1B—C2B	114.0 (3)
O1A—C1A—H1AA	110.6	O1B—C1B—H1BA	110.3
C7A—C1A—H1AA	110.6	C7B—C1B—H1BA	110.3
C2A—C1A—H1AA	110.6	C2B—C1B—H1BA	110.3
C3A—C2A—C8A	113.3 (3)	C3B—C2B—C8B	113.0 (3)
C3A—C2A—C1A	108.8 (3)	C3B—C2B—C1B	108.0 (3)
C8A—C2A—C1A	112.0 (3)	C8B—C2B—C1B	112.1 (3)
C3A—C2A—H2AA	107.5	C3B—C2B—H2BA	107.9
C8A—C2A—H2AA	107.5	C8B—C2B—H2BA	107.9
C1A—C2A—H2AA	107.5	C1B—C2B—H2BA	107.9
O2A—C3A—C2A	123.2 (3)	O2B—C3B—C2B	123.0 (3)
O2A—C3A—C4A	121.9 (3)	O2B—C3B—C4B	121.9 (3)
C2A—C3A—C4A	114.8 (3)	C2B—C3B—C4B	115.0 (3)
C3A—C4A—C9A	114.5 (3)	C3B—C4B—C9B	113.4 (3)
C3A—C4A—C5A	107.1 (2)	C3B—C4B—C5B	107.0 (2)
C9A—C4A—C5A	112.4 (3)	C9B—C4B—C5B	112.3 (3)
C3A—C4A—H4AA	107.5	C3B—C4B—H4BA	108.0
C9A—C4A—H4AA	107.5	C9B—C4B—H4BA	108.0
C5A—C4A—H4AA	107.5	C5B—C4B—H4BA	108.0
O1A—C5A—C6A	104.9 (2)	O1B—C5B—C4B	109.0 (2)
O1A—C5A—C4A	109.3 (3)	O1B—C5B—C6B	105.1 (2)
C6A—C5A—C4A	113.2 (3)	C4B—C5B—C6B	112.3 (2)
O1A—C5A—H5AA	109.8	O1B—C5B—H5BA	110.1
C6A—C5A—H5AA	109.8	C4B—C5B—H5BA	110.1
C4A—C5A—H5AA	109.8	C6B—C5B—H5BA	110.1
C10A—C6A—C5A	111.5 (2)	C10B—C6B—C5B	113.1 (2)
C10A—C6A—C7A	116.0 (2)	C10B—C6B—C7B	114.6 (2)
C5A—C6A—C7A	101.5 (2)	C5B—C6B—C7B	101.4 (2)
C10A—C6A—H6AA	109.2	C10B—C6B—H6BA	109.1
C5A—C6A—H6AA	109.2	C5B—C6B—H6BA	109.1
C7A—C6A—H6AA	109.2	C7B—C6B—H6BA	109.1
C1A—C7A—C6A	104.8 (2)	C1B—C7B—C6B	104.8 (3)
C1A—C7A—H7AA	110.8	C1B—C7B—H7BA	110.8
C6A—C7A—H7AA	110.8	C6B—C7B—H7BA	110.8
C1A—C7A—H7AB	110.8	C1B—C7B—H7BB	110.8
C6A—C7A—H7AB	110.8	C6B—C7B—H7BB	110.8
H7AA—C7A—H7AB	108.9	H7BA—C7B—H7BB	108.9
C2A—C8A—H8AA	109.5	C2B—C8B—H8BA	109.5
C2A—C8A—H8AB	109.5	C2B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
C2A—C8A—H8AC	109.5	C2B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
C4A—C9A—H9AA	109.5	C4B—C9B—H9BA	109.5
C4A—C9A—H9AB	109.5	C4B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C4A—C9A—H9AC	109.5	C4B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C15A—C10A—C11A	117.8 (3)	C11B—C10B—C15B	118.3 (3)
C15A—C10A—C6A	121.8 (3)	C11B—C10B—C6B	119.6 (3)
C11A—C10A—C6A	120.1 (3)	C15B—C10B—C6B	122.1 (3)
C10A—C11A—C12A	121.1 (3)	C10B—C11B—C12B	120.9 (3)
C10A—C11A—H11A	119.4	C10B—C11B—H11B	119.6
C12A—C11A—H11A	119.4	C12B—C11B—H11B	119.6
C13A—C12A—C11A	120.0 (3)	C13B—C12B—C11B	120.0 (3)
C13A—C12A—H12A	120.0	C13B—C12B—H12B	120.0
C11A—C12A—H12A	120.0	C11B—C12B—H12B	120.0
C12A—C13A—C14A	120.3 (3)	C14B—C13B—C12B	119.9 (3)
C12A—C13A—H13A	119.9	C14B—C13B—H13B	120.0
C14A—C13A—H13A	119.9	C12B—C13B—H13B	120.0
C13A—C14A—C15A	120.0 (3)	C13B—C14B—C15B	120.0 (3)
C13A—C14A—H14A	120.0	C13B—C14B—H14B	120.0
C15A—C14A—H14A	120.0	C15B—C14B—H14B	120.0
C10A—C15A—C14A	120.9 (3)	C10B—C15B—C14B	120.9 (3)
C10A—C15A—H15A	119.6	C10B—C15B—H15B	119.6
C14A—C15A—H15A	119.6	C14B—C15B—H15B	119.6

C7A—C6A—C10A—C15A	−53.1 (4)	C7B—C6B—C10B—C15B	−53.9 (4)
C7A—C6A—C10A—C11A	132.8 (3)	C7B—C6B—C10B—C11B	127.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···O2Bⁱ	1.00	2.56	3.230 (4)	124
C6A—H6AA···O1Aⁱⁱ	1.00	2.55	3.452 (4)	150
C6B—H6BA···O1Bⁱⁱⁱ	1.00	2.54	3.395 (4)	144

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page