4-[4-(Dimethyl­amino)benzyl­idene]-2,6-dimethyl­cyclo­hexa-2,5-dienone

Hampel, N.; Richter, D.; Ofial, A.R.; Mayr, H.; Mayer, P.

doi:10.1107/S1600536809030748

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2102

doi:10.1107/S1600536809030748

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4-[4-(Dimethylamino)benzylidene]-2,6-dimethylcyclohexa-2,5-dienone

Nathalie Hampel,^a Dorothea Richter,^a Armin R. Ofial,^a Herbert Mayr ^a and Peter Mayer ^a ^*

^aLudwig-Maximilians-Universität, Department, Butenandtstrasse 5–13, 81377 München, Germany
^*Correspondence e-mail: pemay@cup.uni-muenchen.de

(Received 2 July 2009; accepted 3 August 2009; online 8 August 2009)

The title compound, C₁₇H₁₉NO, crystallized with two molecules per asymmetric unit. C—H⋯O hydrogen bonds lead to infinite chains along [100]. According to graph-set theory, the descriptor C₁¹(13)C₁¹(13) can be assigned.

Related literature

For a related structure, see: Kawai et al. (2004 ). For background to graph set analysis, see: Bernstein et al. (1995 ); Etter et al. (1990 ). For the preparation, see: Richter et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₉NO
M_r = 253.34
Monoclinic, P 2₁ /c
a = 14.5357 (3) Å
b = 7.2759 (2) Å
c = 27.5473 (5) Å
β = 104.6463 (14)°
V = 2818.74 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.24 × 0.20 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
18635 measured reflections
5725 independent reflections
3685 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.131
S = 1.02
5725 reflections
351 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O1ⁱ	0.98	2.51	3.456 (2)	163
C34—H34B⋯O2ⁱ	0.98	2.36	3.328 (2)	169
Symmetry code: (i) x+1, y, z.

Data collection: COLLECT (Hooft, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030748/fl2253sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030748/fl2253Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of (I) contains two complete molecules of the title compound. Figure 1 shows one of the two independent molecules.

A major difference between the two symmetrically independent molecules is found in the angle formed by the planes of the two C₆-rings within a molecule. This angle is found to be 35.19 (7)° between the planes in one molecule but only 20.00 (7)° between the planes in the other molecule (Fig. 2). With a bulky naphthyl substituent at the C atom linking the two rings, an angle of 43.16 (6)° is observed [Kawai et al. (2004)].

The molecular packing, which is shown in Figure 3, is dominated by two C—H···O hydrogen bonds leading to infinite chains along [100]. Each of the chains is built up by 13 atoms and contains one donor atom and one acceptor atom. According to graph set theory [Bernstein et al. (1995), Etter et al. (1990)] the descriptor C₁¹(13)C₁¹(13) can be assigned. The strands are cross-linked by very weak C—H···C contacts with H···C distances of at least 2.79 Å (Table 1).

Related literature top

For a related structure, see: Kawai et al. (2004). For background to graph set analysis, see: Bernstein et al. (1995); Etter et al. (1990). For the preparation, see: Richter et al. (2009).

Experimental top

The title compound was prepared under an atmosphere of dry N₂ from (4-hydroxy-3,5-dimethylphenyl)[4-(dimethylamino)phenyl]methanol [Richter et al. (2009)] (200 mg, 0.737 mmol) that was dissolved in dry CH₂Cl₂ (60 ml) and cooled to 0 °C. Then etheral HBF₄-solution (0.110 ml, 0.811 mmol) was added at 0 °C. After 5 min, NEt₃ (0.133 ml, 0.958 mmol) was added. The cooling bath was removed and stirring was continued for 3 h before the mixture was washed with water (3 times). The organic layer was dried (MgSO₄) and the solvent was removed under reduced pressure. Crystals were obtained by slow cooling of a warm solution of the title compound in acetonitrile. Yield: 149 mg (80%), mp 127–128 °C.

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound (one molecule out of two of the asymmetric unit), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. Schematic representation of the different orientations of the aromatic planes in the two molecules, viewed along the C–H bond of the linking group and parallel to the dienone ring planes. For clarity all atoms connected to the aromatic rings have been omitted.
	Fig. 3. The packing of the title compound, viewed along [010]. Dashed lines indicate hydrogen bonds of the type C—H···O. The solid, red bonds link the 13 atoms involved in one of the two different hydrogen bonds leading to chains along [100].

4-[4-(Dimethylamino)benzylidene]-2,6-dimethylcyclohexa-2,5-dienone top

Crystal data top

C₁₇H₁₉NO	F(000) = 1088
M_r = 253.34	D_x = 1.194 (1) Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10514 reflections
a = 14.5357 (3) Å	θ = 3.1–26.4°
b = 7.2759 (2) Å	µ = 0.07 mm⁻¹
c = 27.5473 (5) Å	T = 200 K
β = 104.6463 (14)°	Block, red
V = 2818.74 (11) Å³	0.24 × 0.20 × 0.19 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	3685 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.051
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 26.4°, θ_min = 3.2°
Detector resolution: 9 pixels mm^-1	h = −18→18
CCD; rotation images; thick slices, ϕ/ω scan	k = −9→9
18635 measured reflections	l = −33→34
5725 independent 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)² + 0.2713P] where P = (F_o² + 2F_c²)/3
5725 reflections	(Δ/σ)_max = 0.001
351 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₉NO	V = 2818.74 (11) Å³
M_r = 253.34	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5357 (3) Å	µ = 0.07 mm⁻¹
b = 7.2759 (2) Å	T = 200 K
c = 27.5473 (5) Å	0.24 × 0.20 × 0.19 mm
β = 104.6463 (14)°

Data collection top

Nonius KappaCCD diffractometer	3685 reflections with I > 2σ(I)
18635 measured reflections	R_int = 0.051
5725 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
5725 reflections	Δρ_min = −0.18 e Å⁻³
351 parameters

Special details top

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 > 2σ(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
O1	−0.31746 (8)	0.77657 (19)	0.46546 (5)	0.0626 (4)
N1	0.37909 (9)	0.7322 (2)	0.45672 (5)	0.0497 (4)
C1	−0.24976 (11)	0.7798 (2)	0.44563 (6)	0.0428 (4)
C2	−0.26523 (11)	0.7680 (2)	0.39087 (6)	0.0441 (4)
C3	−0.19006 (11)	0.7670 (2)	0.37098 (6)	0.0425 (4)
H3	−0.2014	0.7639	0.3355	0.051*
C4	−0.09286 (11)	0.7703 (2)	0.40056 (6)	0.0374 (4)
C5	−0.07886 (11)	0.7914 (2)	0.45418 (5)	0.0372 (4)
H5	−0.0157	0.7992	0.4747	0.045*
C6	−0.15154 (11)	0.8003 (2)	0.47623 (5)	0.0372 (4)
C7	−0.36678 (12)	0.7568 (3)	0.35963 (7)	0.0621 (5)
H7A	−0.3675	0.7544	0.3240	0.093*
H7B	−0.4022	0.8642	0.3664	0.093*
H7C	−0.3964	0.6446	0.3682	0.093*
C8	−0.13802 (12)	0.8369 (2)	0.53118 (6)	0.0477 (4)
H8A	−0.0699	0.8458	0.5475	0.072*
H8B	−0.1660	0.7362	0.5463	0.072*
H8C	−0.1693	0.9527	0.5357	0.072*
C9	−0.02032 (11)	0.7623 (2)	0.37695 (6)	0.0394 (4)
H9	−0.0399	0.7699	0.3414	0.047*
C10	0.08090 (10)	0.7442 (2)	0.39752 (5)	0.0350 (4)
C11	0.14350 (11)	0.8184 (2)	0.37151 (5)	0.0395 (4)
H11	0.1179	0.8716	0.3394	0.047*
C12	0.24043 (11)	0.8172 (2)	0.39054 (6)	0.0413 (4)
H12	0.2798	0.8735	0.3720	0.050*
C13	0.28220 (11)	0.7344 (2)	0.43683 (6)	0.0385 (4)
C14	0.22023 (11)	0.6473 (2)	0.46155 (5)	0.0395 (4)
H14	0.2461	0.5826	0.4919	0.047*
C15	0.12351 (11)	0.6539 (2)	0.44275 (5)	0.0370 (4)
H15	0.0840	0.5956	0.4608	0.044*
C16	0.41687 (13)	0.6822 (3)	0.50911 (7)	0.0713 (6)
H16A	0.3946	0.7704	0.5305	0.107*
H16B	0.4865	0.6838	0.5173	0.107*
H16C	0.3949	0.5586	0.5149	0.107*
C17	0.43927 (13)	0.8433 (3)	0.43384 (8)	0.0752 (6)
H17A	0.4262	0.8142	0.3980	0.113*
H17B	0.5061	0.8173	0.4500	0.113*
H17C	0.4262	0.9737	0.4380	0.113*
O2	−0.37910 (8)	0.25472 (19)	0.34392 (5)	0.0634 (4)
N2	0.33071 (9)	0.24688 (19)	0.33231 (5)	0.0443 (4)
C18	−0.30784 (12)	0.2279 (2)	0.32776 (6)	0.0444 (4)
C19	−0.31707 (11)	0.1739 (2)	0.27539 (6)	0.0410 (4)
C20	−0.23808 (10)	0.1486 (2)	0.25927 (6)	0.0386 (4)
H20	−0.2453	0.1116	0.2254	0.046*
C21	−0.14294 (10)	0.1744 (2)	0.29038 (5)	0.0348 (4)
C22	−0.13547 (11)	0.2196 (2)	0.34218 (6)	0.0387 (4)
H22	−0.0739	0.2329	0.3641	0.046*
C23	−0.21173 (11)	0.2438 (2)	0.36091 (6)	0.0404 (4)
C24	−0.41593 (11)	0.1501 (3)	0.24209 (7)	0.0547 (5)
H24A	−0.4121	0.1181	0.2081	0.082*
H24B	−0.4515	0.2651	0.2411	0.082*
H24C	−0.4485	0.0516	0.2554	0.082*
C25	−0.20350 (13)	0.2812 (3)	0.41543 (6)	0.0535 (5)
H25A	−0.1363	0.2953	0.4331	0.080*
H25B	−0.2309	0.1783	0.4300	0.080*
H25C	−0.2379	0.3944	0.4188	0.080*
C26	−0.06843 (10)	0.1560 (2)	0.26859 (5)	0.0348 (4)
H26	−0.0867	0.1124	0.2350	0.042*
C27	0.03223 (10)	0.1899 (2)	0.28665 (5)	0.0322 (4)
C28	0.09255 (10)	0.1161 (2)	0.25908 (5)	0.0344 (4)
H28	0.0648	0.0509	0.2291	0.041*
C29	0.18928 (10)	0.1334 (2)	0.27339 (5)	0.0356 (4)
H29	0.2268	0.0777	0.2538	0.043*
C30	0.23412 (10)	0.2326 (2)	0.31684 (5)	0.0337 (4)
C31	0.17424 (10)	0.3170 (2)	0.34342 (5)	0.0352 (4)
H31	0.2015	0.3904	0.3720	0.042*
C32	0.07772 (10)	0.2950 (2)	0.32885 (5)	0.0340 (4)
H32	0.0399	0.3529	0.3479	0.041*
C33	0.37588 (11)	0.3514 (3)	0.37678 (6)	0.0547 (5)
H33A	0.3545	0.4795	0.3724	0.082*
H33B	0.4451	0.3468	0.3820	0.082*
H33C	0.3586	0.2987	0.4060	0.082*
C34	0.39029 (11)	0.1576 (3)	0.30456 (7)	0.0613 (5)
H34A	0.3789	0.0247	0.3038	0.092*
H34B	0.4572	0.1823	0.3209	0.092*
H34C	0.3751	0.2051	0.2702	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0423 (7)	0.0853 (11)	0.0637 (8)	−0.0013 (7)	0.0201 (6)	0.0060 (7)
N1	0.0368 (8)	0.0599 (10)	0.0510 (9)	−0.0005 (7)	0.0087 (7)	−0.0015 (7)
C1	0.0380 (10)	0.0389 (10)	0.0521 (10)	0.0030 (7)	0.0124 (8)	0.0058 (8)
C2	0.0385 (10)	0.0414 (11)	0.0488 (10)	0.0007 (8)	0.0045 (8)	0.0039 (8)
C3	0.0431 (10)	0.0449 (11)	0.0361 (9)	0.0003 (8)	0.0036 (7)	0.0007 (7)
C4	0.0378 (9)	0.0333 (9)	0.0386 (9)	0.0011 (7)	0.0053 (7)	−0.0010 (7)
C5	0.0364 (9)	0.0357 (10)	0.0375 (9)	0.0031 (7)	0.0055 (7)	−0.0011 (7)
C6	0.0435 (10)	0.0293 (9)	0.0387 (9)	0.0022 (7)	0.0099 (7)	0.0004 (7)
C7	0.0396 (10)	0.0792 (15)	0.0615 (12)	−0.0030 (10)	0.0018 (8)	0.0074 (10)
C8	0.0514 (11)	0.0480 (11)	0.0455 (10)	0.0000 (8)	0.0158 (8)	−0.0053 (8)
C9	0.0430 (10)	0.0396 (10)	0.0343 (8)	0.0027 (7)	0.0075 (7)	−0.0001 (7)
C10	0.0376 (9)	0.0342 (9)	0.0333 (8)	0.0021 (7)	0.0093 (7)	−0.0037 (7)
C11	0.0481 (11)	0.0388 (10)	0.0329 (8)	0.0061 (8)	0.0129 (7)	0.0021 (7)
C12	0.0440 (10)	0.0403 (10)	0.0444 (9)	0.0017 (8)	0.0199 (8)	0.0006 (8)
C13	0.0370 (9)	0.0378 (10)	0.0410 (9)	0.0029 (7)	0.0108 (7)	−0.0065 (7)
C14	0.0435 (10)	0.0419 (10)	0.0330 (8)	0.0071 (8)	0.0096 (7)	0.0011 (7)
C15	0.0418 (10)	0.0361 (10)	0.0356 (8)	0.0032 (7)	0.0144 (7)	0.0003 (7)
C16	0.0454 (11)	0.1020 (18)	0.0574 (12)	0.0055 (11)	−0.0036 (9)	−0.0013 (11)
C17	0.0449 (12)	0.0843 (17)	0.0953 (16)	−0.0098 (11)	0.0155 (11)	0.0064 (13)
O2	0.0438 (7)	0.0777 (10)	0.0766 (9)	−0.0019 (6)	0.0296 (7)	−0.0172 (7)
N2	0.0300 (8)	0.0539 (10)	0.0487 (8)	−0.0022 (6)	0.0097 (6)	−0.0082 (7)
C18	0.0397 (10)	0.0411 (11)	0.0572 (11)	−0.0015 (8)	0.0210 (8)	−0.0019 (8)
C19	0.0327 (9)	0.0379 (10)	0.0519 (10)	−0.0006 (7)	0.0099 (7)	−0.0001 (8)
C20	0.0365 (9)	0.0383 (10)	0.0398 (9)	−0.0006 (7)	0.0073 (7)	−0.0029 (7)
C21	0.0339 (9)	0.0324 (9)	0.0375 (8)	0.0014 (7)	0.0081 (7)	0.0002 (7)
C22	0.0337 (9)	0.0408 (10)	0.0400 (9)	−0.0033 (7)	0.0066 (7)	0.0003 (7)
C23	0.0436 (10)	0.0369 (10)	0.0437 (9)	−0.0036 (7)	0.0165 (8)	−0.0023 (7)
C24	0.0359 (10)	0.0649 (13)	0.0630 (11)	−0.0020 (9)	0.0117 (8)	−0.0051 (9)
C25	0.0613 (12)	0.0562 (13)	0.0482 (10)	−0.0044 (9)	0.0237 (9)	−0.0043 (9)
C26	0.0331 (9)	0.0354 (9)	0.0345 (8)	0.0013 (7)	0.0060 (7)	−0.0011 (7)
C27	0.0324 (9)	0.0325 (9)	0.0314 (8)	0.0024 (7)	0.0074 (6)	0.0025 (6)
C28	0.0370 (9)	0.0363 (9)	0.0296 (8)	−0.0012 (7)	0.0080 (6)	0.0004 (6)
C29	0.0365 (9)	0.0372 (10)	0.0366 (8)	0.0007 (7)	0.0159 (7)	−0.0013 (7)
C30	0.0284 (8)	0.0368 (10)	0.0360 (8)	0.0004 (7)	0.0084 (6)	0.0042 (7)
C31	0.0357 (9)	0.0363 (10)	0.0327 (8)	−0.0024 (7)	0.0070 (7)	−0.0022 (7)
C32	0.0335 (9)	0.0352 (9)	0.0342 (8)	0.0021 (7)	0.0104 (7)	−0.0008 (7)
C33	0.0362 (10)	0.0668 (14)	0.0552 (10)	−0.0054 (9)	0.0006 (8)	−0.0090 (9)
C34	0.0337 (10)	0.0803 (15)	0.0735 (13)	−0.0009 (9)	0.0201 (9)	−0.0154 (11)

Geometric parameters (Å, º) top

O1—C1	1.2406 (18)	O2—C18	1.2418 (18)
N1—C13	1.376 (2)	N2—C30	1.3642 (18)
N1—C17	1.447 (2)	N2—C34	1.446 (2)
N1—C16	1.455 (2)	N2—C33	1.450 (2)
C1—C2	1.470 (2)	C18—C23	1.468 (2)
C1—C6	1.471 (2)	C18—C19	1.468 (2)
C2—C3	1.341 (2)	C19—C20	1.344 (2)
C2—C7	1.511 (2)	C19—C24	1.507 (2)
C3—C4	1.442 (2)	C20—C21	1.443 (2)
C3—H3	0.9500	C20—H20	0.9500
C4—C9	1.373 (2)	C21—C26	1.371 (2)
C4—C5	1.447 (2)	C21—C22	1.441 (2)
C5—C6	1.347 (2)	C22—C23	1.347 (2)
C5—H5	0.9500	C22—H22	0.9500
C6—C8	1.500 (2)	C23—C25	1.501 (2)
C7—H7A	0.9800	C24—H24A	0.9800
C7—H7B	0.9800	C24—H24B	0.9800
C7—H7C	0.9800	C24—H24C	0.9800
C8—H8A	0.9800	C25—H25A	0.9800
C8—H8B	0.9800	C25—H25B	0.9800
C8—H8C	0.9800	C25—H25C	0.9800
C9—C10	1.443 (2)	C26—C27	1.4426 (19)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.401 (2)	C27—C28	1.404 (2)
C10—C15	1.406 (2)	C27—C32	1.409 (2)
C11—C12	1.374 (2)	C28—C29	1.367 (2)
C11—H11	0.9500	C28—H28	0.9500
C12—C13	1.402 (2)	C29—C30	1.409 (2)
C12—H12	0.9500	C29—H29	0.9500
C13—C14	1.410 (2)	C30—C31	1.412 (2)
C14—C15	1.371 (2)	C31—C32	1.368 (2)
C14—H14	0.9500	C31—H31	0.9500
C15—H15	0.9500	C32—H32	0.9500
C16—H16A	0.9800	C33—H33A	0.9800
C16—H16B	0.9800	C33—H33B	0.9800
C16—H16C	0.9800	C33—H33C	0.9800
C17—H17A	0.9800	C34—H34A	0.9800
C17—H17B	0.9800	C34—H34B	0.9800
C17—H17C	0.9800	C34—H34C	0.9800

C13—N1—C17	119.38 (14)	C30—N2—C34	120.48 (13)
C13—N1—C16	119.30 (14)	C30—N2—C33	120.93 (13)
C17—N1—C16	116.99 (14)	C34—N2—C33	118.59 (13)
O1—C1—C2	121.20 (15)	O2—C18—C23	120.91 (15)
O1—C1—C6	120.85 (15)	O2—C18—C19	121.12 (15)
C2—C1—C6	117.93 (14)	C23—C18—C19	117.94 (13)
C3—C2—C1	119.39 (14)	C20—C19—C18	119.19 (14)
C3—C2—C7	123.14 (16)	C20—C19—C24	123.09 (15)
C1—C2—C7	117.47 (15)	C18—C19—C24	117.72 (14)
C2—C3—C4	123.54 (15)	C19—C20—C21	123.81 (14)
C2—C3—H3	118.2	C19—C20—H20	118.1
C4—C3—H3	118.2	C21—C20—H20	118.1
C9—C4—C3	119.46 (14)	C26—C21—C22	125.83 (13)
C9—C4—C5	124.14 (14)	C26—C21—C20	118.16 (13)
C3—C4—C5	116.32 (14)	C22—C21—C20	116.00 (13)
C6—C5—C4	122.78 (14)	C23—C22—C21	123.07 (14)
C6—C5—H5	118.6	C23—C22—H22	118.5
C4—C5—H5	118.6	C21—C22—H22	118.5
C5—C6—C1	119.69 (14)	C22—C23—C18	119.83 (14)
C5—C6—C8	123.10 (14)	C22—C23—C25	122.80 (15)
C1—C6—C8	117.18 (14)	C18—C23—C25	117.34 (14)
C2—C7—H7A	109.5	C19—C24—H24A	109.5
C2—C7—H7B	109.5	C19—C24—H24B	109.5
H7A—C7—H7B	109.5	H24A—C24—H24B	109.5
C2—C7—H7C	109.5	C19—C24—H24C	109.5
H7A—C7—H7C	109.5	H24A—C24—H24C	109.5
H7B—C7—H7C	109.5	H24B—C24—H24C	109.5
C6—C8—H8A	109.5	C23—C25—H25A	109.5
C6—C8—H8B	109.5	C23—C25—H25B	109.5
H8A—C8—H8B	109.5	H25A—C25—H25B	109.5
C6—C8—H8C	109.5	C23—C25—H25C	109.5
H8A—C8—H8C	109.5	H25A—C25—H25C	109.5
H8B—C8—H8C	109.5	H25B—C25—H25C	109.5
C4—C9—C10	130.31 (14)	C21—C26—C27	132.61 (14)
C4—C9—H9	114.8	C21—C26—H26	113.7
C10—C9—H9	114.8	C27—C26—H26	113.7
C11—C10—C15	115.83 (13)	C28—C27—C32	115.29 (13)
C11—C10—C9	119.57 (13)	C28—C27—C26	117.75 (13)
C15—C10—C9	124.60 (14)	C32—C27—C26	126.93 (13)
C12—C11—C10	122.60 (14)	C29—C28—C27	123.11 (13)
C12—C11—H11	118.7	C29—C28—H28	118.4
C10—C11—H11	118.7	C27—C28—H28	118.4
C11—C12—C13	121.08 (14)	C28—C29—C30	120.92 (13)
C11—C12—H12	119.5	C28—C29—H29	119.5
C13—C12—H12	119.5	C30—C29—H29	119.5
N1—C13—C12	122.09 (14)	N2—C30—C29	121.54 (13)
N1—C13—C14	121.14 (14)	N2—C30—C31	121.71 (13)
C12—C13—C14	116.74 (14)	C29—C30—C31	116.75 (13)
C15—C14—C13	121.43 (14)	C32—C31—C30	121.21 (13)
C15—C14—H14	119.3	C32—C31—H31	119.4
C13—C14—H14	119.3	C30—C31—H31	119.4
C14—C15—C10	122.08 (14)	C31—C32—C27	122.56 (13)
C14—C15—H15	119.0	C31—C32—H32	118.7
C10—C15—H15	119.0	C27—C32—H32	118.7
N1—C16—H16A	109.5	N2—C33—H33A	109.5
N1—C16—H16B	109.5	N2—C33—H33B	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
N1—C16—H16C	109.5	N2—C33—H33C	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
N1—C17—H17A	109.5	N2—C34—H34A	109.5
N1—C17—H17B	109.5	N2—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
N1—C17—H17C	109.5	N2—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5

O1—C1—C2—C3	−178.22 (16)	O2—C18—C19—C20	179.15 (16)
C6—C1—C2—C3	3.3 (2)	C23—C18—C19—C20	−2.7 (2)
O1—C1—C2—C7	1.5 (2)	O2—C18—C19—C24	−0.6 (2)
C6—C1—C2—C7	−176.94 (15)	C23—C18—C19—C24	177.49 (15)
C1—C2—C3—C4	2.3 (3)	C18—C19—C20—C21	−1.1 (2)
C7—C2—C3—C4	−177.45 (16)	C24—C19—C20—C21	178.72 (15)
C2—C3—C4—C9	177.69 (16)	C19—C20—C21—C26	−175.74 (15)
C2—C3—C4—C5	−5.3 (2)	C19—C20—C21—C22	3.6 (2)
C9—C4—C5—C6	179.44 (15)	C26—C21—C22—C23	176.92 (16)
C3—C4—C5—C6	2.6 (2)	C20—C21—C22—C23	−2.4 (2)
C4—C5—C6—C1	2.9 (2)	C21—C22—C23—C18	−1.3 (2)
C4—C5—C6—C8	−175.02 (15)	C21—C22—C23—C25	176.74 (16)
O1—C1—C6—C5	175.68 (15)	O2—C18—C23—C22	−178.00 (16)
C2—C1—C6—C5	−5.8 (2)	C19—C18—C23—C22	3.9 (2)
O1—C1—C6—C8	−6.3 (2)	O2—C18—C23—C25	3.9 (2)
C2—C1—C6—C8	172.17 (15)	C19—C18—C23—C25	−174.24 (15)
C3—C4—C9—C10	−172.71 (15)	C22—C21—C26—C27	−6.6 (3)
C5—C4—C9—C10	10.5 (3)	C20—C21—C26—C27	172.68 (15)
C4—C9—C10—C11	−151.45 (17)	C21—C26—C27—C28	165.06 (16)
C4—C9—C10—C15	29.2 (3)	C21—C26—C27—C32	−16.9 (3)
C15—C10—C11—C12	−5.2 (2)	C32—C27—C28—C29	4.1 (2)
C9—C10—C11—C12	175.42 (14)	C26—C27—C28—C29	−177.62 (13)
C10—C11—C12—C13	2.4 (2)	C27—C28—C29—C30	−1.7 (2)
C17—N1—C13—C12	10.3 (2)	C34—N2—C30—C29	−0.8 (2)
C16—N1—C13—C12	166.30 (17)	C33—N2—C30—C29	179.24 (15)
C17—N1—C13—C14	−171.83 (16)	C34—N2—C30—C31	179.45 (15)
C16—N1—C13—C14	−15.9 (2)	C33—N2—C30—C31	−0.5 (2)
C11—C12—C13—N1	−179.73 (15)	C28—C29—C30—N2	178.22 (14)
C11—C12—C13—C14	2.3 (2)	C28—C29—C30—C31	−2.0 (2)
N1—C13—C14—C15	177.92 (14)	N2—C30—C31—C32	−177.05 (14)
C12—C13—C14—C15	−4.1 (2)	C29—C30—C31—C32	3.2 (2)
C13—C14—C15—C10	1.3 (2)	C30—C31—C32—C27	−0.7 (2)
C11—C10—C15—C14	3.3 (2)	C28—C27—C32—C31	−2.9 (2)
C9—C10—C15—C14	−177.29 (14)	C26—C27—C32—C31	179.02 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.98	2.51	3.456 (2)	163
C34—H34B···O2ⁱ	0.98	2.36	3.328 (2)	169

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO
M_r	253.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	14.5357 (3), 7.2759 (2), 27.5473 (5)
β (°)	104.6463 (14)
V (Å³)	2818.74 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.20 × 0.19

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18635, 5725, 3685
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.131, 1.02
No. of reflections	5725
No. of parameters	351
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: COLLECT (Hooft, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.98	2.51	3.456 (2)	163
C34—H34B···O2ⁱ	0.98	2.36	3.328 (2)	169

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. W. W. (2004). COLLECT. Bruker–Nonius BV, Delft, The Netherlands. Google Scholar
Kawai, H., Nagasu, T., Takeda, T., Fujiwara, K., Tsuji, T., Ohkita, M., Nishida, J. & Suzuki, T. (2004). Tetrahedron Lett. 45, 4553–4558. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Richter, D., Hampel, N., Singer, T., Ofial, A. R. & Mayr, H. (2009). Eur. J. Org. Chem. pp. 3203–3211. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar