2-(6-Methyl-2-pyrid­yl)-1,1-diphenyl­ethanol

Gu, W.-J.; Wang, B.-X.

doi:10.1107/S1600536808025026

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1725

doi:10.1107/S1600536808025026

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2-(6-Methyl-2-pyridyl)-1,1-diphenylethanol

Wei-Jin Gu ^a ^* and Bing-Xiang Wang ^a

^aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China
^*Correspondence e-mail: llyyjz@nju.edu.cn

(Received 11 July 2008; accepted 4 August 2008; online 9 August 2008)

The title compound, C₂₀H₁₉NO, was prepared from 2,6-lutidine and benzophenone. There are two symmetry-independent molecules in the asymmetric unit. Each molecule is involved in one intramolecular O—H⋯N hydrogen bond. In the crystal structure, helical chains are formed along the b axis by weak π–π interactions between neighbouring molecules [centroid–centroid distances between the pyridyl rings of the two independent molecules = 4.041 (3) and 4.051 (3) Å].

Related literature

For related literature, see: Berg & Holm (1985 ); Dehnicke et al. (2001 ); Gibson et al. (2007 ); Koning et al. (2000 ); Yip et al. (2003 ).

Experimental

Crystal data

C₂₀H₁₉NO
M_r = 289.36
Monoclinic, P 2₁ /c
a = 13.466 (2) Å
b = 8.022 (1) Å
c = 30.220 (3) Å
β = 102.874 (3)°
V = 3182.4 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.98, T_max = 0.98
24109 measured reflections
6247 independent reflections
4901 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.116
S = 1.02
6247 reflections
405 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.96 (2)	1.89 (2)	2.724 (2)	144 (2)
O2—H2A⋯N2	0.96 (2)	1.92 (2)	2.718 (2)	139 (2)
C18—H18⋯O2ⁱ	0.93	2.70	3.518 (2)	147
C38—H38⋯O1ⁱⁱ	0.93	2.65	3.472 (2)	147
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025026/im2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025026/im2078Isup2.hkl

checkCIF report

Comment top

There is a growing interest in the chemistry of metal-nitrido complexes, particularly those of late transition metals (Dehnicke et al., 2001). 2-(6-Methyl-pyridin-2-yl)-1,1-diphenyl-ethanol has been used as a multianionic chelating (N, O) ligand and coordinated with transition metals and main group elements, such as Ru, Os, Mo, B, Si etc. (Yip et al., 2003; Gibson et al., 2007). It can be prepared from 2,6-lutidine in moderate yield (Koning et al., 2000). During our studies, we obtained single crystals of the title compound report its crystal structure herein.

The crystal structure of title compound, C₂₀H₁₉NO, shows that all the bond lengths and angles have normal values. In an asymmetric unit there are two symmetry independent molecules I and II. Each molecule has one intramolecular O—H···N hydrogen bond (O1—H1A···N1, O2—H2A···N2)(Fig. 1).

Molecule I exhibits two benzene rings A (C2—C7) and B (C8—C13) as well as a pyridine ring C (N1/C15—C19) that are not coplanar with respect to each other. The dihedral angles between rings A and B, B and C, and C and A measure to 82.02 (6)°, 47.06 (6)°, and 85.87 (5)°, respectively.

Molecule II looks pretty much the same as molecule I, but the dihedral angles are significantly different. The angles between rings D(C22—C27) and E(C28—C33), E and F(N2/C35—C39), and F and D are 83.58 (6)°, 85.44 (5)°, and 49.70 (6)°, respectively.

In the crystal packing weak π–π interactions between neighbouring molecules I and II are observed, the distance of g1-g2 being 4.041 (3) and 4.051 (3) Å (g1 is center of mass of N1/C15—C19, g2 is center of mass of N2/C35—C39). Helical chains along the b axis are formed by these interactions (Fig. 2).

The additional weak intermolecular C18—H18···O2ⁱⁱⁱ and C38—H38···O1^iv (iii: -x,1 - y,-z; iv: 1 - x,1 - y,-z) hydrogen bonds play part an important role linking the helical chains to form the three-dimensional crystal structure.

Related literature top

For related literature, see: Berg & Holm (1985); Dehnicke et al. (2001); Gibson et al. (2007); Koning et al. (2000); Yip et al. (2003).

Experimental top

2-(6-Methyl-pyridin-2-yl)-1,1-diphenyl-ethanol was prepared from 2,6-lutidine and benzophenone according to a procedure described in the literature (Berg & Holm, 1985, yield: 60%). Colorless crystals were obtained by recrystallization from light petroleum-ethyl acetate(vol. ratio: 5:1) at room temperature.

¹H-NMR (CDCl₃, 400 MHz): δ = 8.1 (1 H, s, OH), 6.8–7.5 (13 H, 2 Ph + 3H), 3.7 (2 H, s, CH₂), 2.5 (3 H, s, CH₃).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at 30% probability level. Dashed lines indicate hydrogen bonds and all H atoms except those involved in hydrogen bonding have been omitted for clarity.
	Fig. 2. A view of the helical chain-like structure along the b axis. (i: x,1 + y,z; ii:x,-1 + y,z).

2-(6-Methyl-2-pyridyl)-1,1-diphenylethanol top

Crystal data top

C₂₀H₁₉NO	F(000) = 1232
M_r = 289.36	D_x = 1.208 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9992 reflections
a = 13.466 (2) Å	θ = 2.3–27.7°
b = 8.022 (1) Å	µ = 0.07 mm⁻¹
c = 30.220 (3) Å	T = 291 K
β = 102.874 (3)°	Bloc, colourless
V = 3182.4 (7) Å³	0.30 × 0.26 × 0.24 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	6247 independent reflections
Radiation source: sealed tube	4901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
T_min = 0.98, T_max = 0.98	k = −9→9
24109 measured reflections	l = −36→37

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) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.05P)² + 0.55P] where P = (F_o² + 2F_c²)/3
6247 reflections	(Δ/σ)_max < 0.001
405 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₀H₁₉NO	V = 3182.4 (7) Å³
M_r = 289.36	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.466 (2) Å	µ = 0.07 mm⁻¹
b = 8.022 (1) Å	T = 291 K
c = 30.220 (3) Å	0.30 × 0.26 × 0.24 mm
β = 102.874 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	6247 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4901 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.98	R_int = 0.039
24109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.12 e Å⁻³
6247 reflections	Δρ_min = −0.12 e Å⁻³
405 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.9264 (0.0081) x + 2.5384 (0.0055) y + 17.9519 (0.0173) z = 7.2409 (0.0023)

* 0.0041 (0.0011) C2 * -0.0032 (0.0012) C3 * 0.0016 (0.0013) C4 * -0.0007 (0.0013) C5 * 0.0017 (0.0013) C6 * -0.0033 (0.0012) C7

Rms deviation of fitted atoms = 0.0027

8.6157 (0.0075) x - 6.1646 (0.0038) y - 4.0922 (0.0231) z = 2.4746 (0.0072)

Angle to previous plane (with approximate e.s.d.) = 82.02 (0.06)

* -0.0038 (0.0011) C8 * 0.0059 (0.0011) C9 * -0.0038 (0.0013) C10 * -0.0004 (0.0014) C11 * 0.0025 (0.0014) C12 * -0.0004 (0.0012) C13

Rms deviation of fitted atoms = 0.0034

- 0.0031 (0.0098) x + 7.0734 (0.0030) y - 13.8930 (0.0198) z = 1.4744 (0.0034)

Angle to previous plane (with approximate e.s.d.) = 47.06 (0.06)

* 0.0019 (0.0011) N1 * 0.0034 (0.0011) C15 * -0.0039 (0.0012) C16 * -0.0005 (0.0014) C17 * 0.0056 (0.0014) C18 * -0.0064 (0.0012) C19

Rms deviation of fitted atoms = 0.0041

7.9264 (0.0081) x + 2.5384 (0.0055) y + 17.9519 (0.0173) z = 7.2409 (0.0023)

Angle to previous plane (with approximate e.s.d.) = 85.87 (0.05)

* 0.0041 (0.0011) C2 * -0.0032 (0.0012) C3 * 0.0016 (0.0013) C4 * -0.0007 (0.0013) C5 * 0.0017 (0.0013) C6 * -0.0033 (0.0012) C7

Rms deviation of fitted atoms = 0.0027

8.6502 (0.0076) x + 6.1357 (0.0039) y - 2.9169 (0.0234) z = 5.1262 (0.0059)

Angle to previous plane (with approximate e.s.d.) = 49.02 (0.07)

* -0.0040 (0.0011) C22 * 0.0029 (0.0013) C23 * -0.0003 (0.0014) C24 * -0.0010 (0.0014) C25 * -0.0002 (0.0013) C26 * 0.0028 (0.0012) C27

Rms deviation of fitted atoms = 0.0024

- 8.0302 (0.0080) x + 2.4726 (0.0054) y + 25.8511 (0.0117) z = 4.4687 (0.0039)

Angle to previous plane (with approximate e.s.d.) = 83.58 (0.06)

* 0.0063 (0.0011) C28 * -0.0023 (0.0012) C29 * -0.0051 (0.0013) C30 * 0.0085 (0.0014) C31 * -0.0043 (0.0013) C32 * -0.0032 (0.0012) C33

Rms deviation of fitted atoms = 0.0053

- 0.0603 (0.0094) x + 7.0521 (0.0030) y - 14.0087 (0.0195) z = 4.9759 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 85.44 (0.05)

* -0.0024 (0.0011) N2 * 0.0054 (0.0011) C35 * -0.0025 (0.0012) C36 * -0.0031 (0.0013) C37 * 0.0060 (0.0013) C38 * -0.0034 (0.0012) C39

Rms deviation of fitted atoms = 0.0040

8.6502 (0.0076) x + 6.1357 (0.0039) y - 2.9169 (0.0234) z = 5.1262 (0.0059)

Angle to previous plane (with approximate e.s.d.) = 49.70 (0.06)

* -0.0040 (0.0011) C22 * 0.0029 (0.0013) C23 * -0.0003 (0.0014) C24 * -0.0010 (0.0014) C25 * -0.0002 (0.0013) C26 * 0.0028 (0.0012) C27

Rms deviation of fitted atoms = 0.0024

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
C1	0.55525 (11)	0.30363 (18)	0.12015 (5)	0.0333 (3)
C2	0.52945 (10)	0.15683 (18)	0.14763 (5)	0.0333 (3)
C3	0.46070 (12)	0.1698 (2)	0.17575 (5)	0.0432 (4)
H3	0.4257	0.2692	0.1767	0.052*
C4	0.44374 (14)	0.0364 (3)	0.20236 (6)	0.0552 (5)
H4	0.3981	0.0474	0.2212	0.066*
C5	0.49408 (16)	−0.1119 (3)	0.20098 (7)	0.0631 (5)
H5	0.4823	−0.2014	0.2187	0.076*
C6	0.56142 (15)	−0.1273 (2)	0.17356 (7)	0.0606 (5)
H6	0.5959	−0.2274	0.1728	0.073*
C7	0.57882 (12)	0.0055 (2)	0.14681 (6)	0.0458 (4)
H7	0.6244	−0.0072	0.1280	0.055*
C8	0.64575 (11)	0.40377 (18)	0.14754 (5)	0.0364 (3)
C9	0.67094 (12)	0.4062 (2)	0.19461 (6)	0.0428 (4)
H9	0.6339	0.3416	0.2108	0.051*
C10	0.75135 (13)	0.5046 (2)	0.21792 (7)	0.0546 (5)
H10	0.7665	0.5063	0.2495	0.065*
C11	0.80791 (14)	0.5984 (2)	0.19495 (8)	0.0640 (6)
H11	0.8616	0.6630	0.2107	0.077*
C12	0.78427 (14)	0.5961 (3)	0.14796 (9)	0.0674 (6)
H12	0.8224	0.6593	0.1320	0.081*
C13	0.70373 (13)	0.4996 (2)	0.12451 (7)	0.0517 (4)
H13	0.6885	0.4992	0.0929	0.062*
C14	0.46541 (11)	0.42749 (19)	0.10506 (5)	0.0381 (3)
H14A	0.4463	0.4708	0.1320	0.046*
H14B	0.4889	0.5207	0.0897	0.046*
C15	0.37153 (11)	0.35434 (19)	0.07395 (5)	0.0395 (3)
C16	0.27485 (13)	0.3698 (2)	0.08237 (6)	0.0511 (4)
H16	0.2649	0.4206	0.1087	0.061*
C17	0.19352 (14)	0.3071 (3)	0.05024 (8)	0.0628 (5)
H17	0.1277	0.3158	0.0548	0.075*
C18	0.20984 (15)	0.2327 (3)	0.01190 (7)	0.0642 (5)
H18	0.1552	0.1917	−0.0098	0.077*
C19	0.30793 (15)	0.2184 (2)	0.00548 (6)	0.0542 (5)
C20	0.3320 (2)	0.1393 (3)	−0.03588 (7)	0.0780 (7)
H20A	0.3601	0.2215	−0.0527	0.117*
H20B	0.2708	0.0944	−0.0546	0.117*
H20C	0.3806	0.0512	−0.0268	0.117*
C21	0.06735 (10)	0.80270 (18)	0.12103 (5)	0.0333 (3)
C22	0.00363 (11)	0.90017 (18)	0.14826 (5)	0.0356 (3)
C23	−0.07527 (13)	1.0013 (2)	0.12473 (7)	0.0519 (4)
H23	−0.0884	1.0060	0.0932	0.062*
C24	−0.13383 (15)	1.0943 (3)	0.14768 (9)	0.0668 (6)
H24	−0.1863	1.1604	0.1316	0.080*
C25	−0.11486 (15)	1.0896 (3)	0.19424 (8)	0.0659 (6)
H25	−0.1544	1.1524	0.2097	0.079*
C26	−0.03709 (15)	0.9914 (3)	0.21801 (7)	0.0578 (5)
H26	−0.0241	0.9879	0.2495	0.069*
C27	0.02182 (12)	0.8979 (2)	0.19507 (6)	0.0424 (4)
H27	0.0744	0.8326	0.2114	0.051*
C28	0.12469 (11)	0.65852 (18)	0.14885 (5)	0.0350 (3)
C29	0.07775 (13)	0.5045 (2)	0.14868 (6)	0.0471 (4)
H29	0.0135	0.4876	0.1302	0.057*
C30	0.12589 (15)	0.3745 (2)	0.17595 (7)	0.0566 (5)
H30	0.0939	0.2716	0.1754	0.068*
C31	0.22188 (17)	0.3991 (3)	0.20394 (7)	0.0643 (6)
H31	0.2533	0.3132	0.2226	0.077*
C32	0.26986 (14)	0.5481 (3)	0.20410 (6)	0.0576 (5)
H32	0.3346	0.5633	0.2224	0.069*
C33	0.22213 (12)	0.6781 (2)	0.17688 (6)	0.0453 (4)
H33	0.2555	0.7798	0.1773	0.054*
C34	0.14015 (11)	0.92662 (19)	0.10486 (5)	0.0382 (3)
H34A	0.1001	1.0187	0.0895	0.046*
H34B	0.1868	0.9716	0.1313	0.046*
C35	0.20135 (12)	0.85435 (19)	0.07364 (5)	0.0396 (3)
C36	0.30642 (13)	0.8702 (2)	0.08174 (6)	0.0502 (4)
H36	0.3428	0.9219	0.1079	0.060*
C37	0.35558 (15)	0.8070 (3)	0.04974 (7)	0.0596 (5)
H37	0.4260	0.8155	0.0542	0.072*
C38	0.29968 (16)	0.7313 (3)	0.01125 (7)	0.0600 (5)
H38	0.3320	0.6899	−0.0106	0.072*
C39	0.19560 (14)	0.7175 (2)	0.00542 (6)	0.0482 (4)
C40	0.12872 (14)	0.6369 (3)	−0.03596 (6)	0.0563 (5)
H40A	0.0893	0.5496	−0.0265	0.084*
H40B	0.1707	0.5909	−0.0548	0.084*
H40C	0.0838	0.7190	−0.0528	0.084*
N1	0.38751 (11)	0.28000 (18)	0.03621 (5)	0.0465 (3)
N2	0.14697 (11)	0.77822 (18)	0.03610 (4)	0.0443 (3)
O1	0.58575 (9)	0.24349 (15)	0.08070 (4)	0.0458 (3)
H1A	0.5263 (15)	0.224 (2)	0.0571 (7)	0.055*
O2	−0.00304 (8)	0.73711 (15)	0.08224 (4)	0.0461 (3)
H2A	0.0333 (14)	0.704 (2)	0.0597 (7)	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0323 (7)	0.0332 (8)	0.0356 (8)	0.0010 (6)	0.0103 (6)	−0.0029 (6)
C2	0.0291 (7)	0.0338 (8)	0.0351 (7)	−0.0038 (6)	0.0027 (6)	−0.0047 (6)
C3	0.0417 (8)	0.0466 (9)	0.0436 (9)	−0.0030 (7)	0.0146 (7)	−0.0015 (7)
C4	0.0530 (10)	0.0646 (12)	0.0495 (10)	−0.0135 (9)	0.0148 (8)	0.0080 (9)
C5	0.0647 (12)	0.0560 (12)	0.0610 (12)	−0.0183 (10)	−0.0023 (10)	0.0204 (9)
C6	0.0569 (11)	0.0378 (10)	0.0798 (14)	0.0043 (8)	−0.0008 (10)	0.0102 (9)
C7	0.0401 (8)	0.0391 (9)	0.0561 (10)	0.0027 (7)	0.0065 (7)	−0.0017 (8)
C8	0.0307 (7)	0.0302 (8)	0.0489 (9)	0.0009 (6)	0.0102 (6)	−0.0020 (6)
C9	0.0385 (8)	0.0392 (9)	0.0494 (9)	−0.0045 (7)	0.0068 (7)	−0.0033 (7)
C10	0.0436 (9)	0.0513 (11)	0.0611 (11)	−0.0020 (8)	−0.0049 (8)	−0.0105 (9)
C11	0.0385 (9)	0.0465 (11)	0.0987 (17)	−0.0098 (8)	−0.0023 (10)	−0.0058 (11)
C12	0.0469 (10)	0.0524 (12)	0.1050 (18)	−0.0139 (9)	0.0211 (11)	0.0117 (11)
C13	0.0443 (9)	0.0479 (10)	0.0662 (11)	−0.0051 (8)	0.0193 (8)	0.0040 (9)
C14	0.0393 (8)	0.0325 (8)	0.0418 (8)	0.0032 (6)	0.0075 (6)	−0.0001 (6)
C15	0.0403 (8)	0.0361 (8)	0.0392 (8)	0.0003 (7)	0.0028 (6)	0.0067 (7)
C16	0.0428 (9)	0.0538 (11)	0.0550 (11)	0.0043 (8)	0.0069 (8)	0.0088 (8)
C17	0.0388 (9)	0.0658 (13)	0.0780 (14)	0.0004 (9)	0.0004 (9)	0.0173 (11)
C18	0.0563 (12)	0.0600 (12)	0.0630 (13)	−0.0040 (9)	−0.0149 (10)	0.0084 (10)
C19	0.0618 (11)	0.0499 (10)	0.0410 (9)	−0.0058 (8)	−0.0094 (8)	0.0105 (8)
C20	0.0978 (17)	0.0816 (16)	0.0469 (11)	−0.0147 (13)	0.0000 (11)	−0.0097 (11)
C21	0.0297 (7)	0.0333 (8)	0.0354 (8)	−0.0033 (6)	0.0039 (6)	−0.0029 (6)
C22	0.0314 (7)	0.0322 (8)	0.0436 (8)	−0.0046 (6)	0.0089 (6)	−0.0031 (6)
C23	0.0426 (9)	0.0504 (10)	0.0614 (11)	0.0094 (8)	0.0088 (8)	0.0026 (9)
C24	0.0529 (11)	0.0522 (11)	0.0984 (17)	0.0163 (9)	0.0234 (11)	0.0044 (11)
C25	0.0562 (11)	0.0584 (12)	0.0924 (16)	0.0027 (10)	0.0364 (11)	−0.0182 (11)
C26	0.0574 (11)	0.0637 (12)	0.0583 (11)	−0.0056 (9)	0.0255 (9)	−0.0131 (10)
C27	0.0399 (8)	0.0429 (9)	0.0448 (9)	−0.0023 (7)	0.0107 (7)	−0.0035 (7)
C28	0.0368 (7)	0.0336 (8)	0.0365 (8)	0.0025 (6)	0.0126 (6)	−0.0010 (6)
C29	0.0468 (9)	0.0380 (9)	0.0607 (11)	−0.0035 (7)	0.0208 (8)	−0.0030 (8)
C30	0.0602 (11)	0.0348 (9)	0.0875 (14)	0.0008 (8)	0.0433 (11)	0.0106 (9)
C31	0.0749 (13)	0.0558 (12)	0.0683 (13)	0.0251 (10)	0.0294 (11)	0.0240 (10)
C32	0.0510 (10)	0.0640 (12)	0.0543 (11)	0.0131 (9)	0.0043 (8)	0.0124 (9)
C33	0.0422 (9)	0.0409 (9)	0.0497 (10)	0.0003 (7)	0.0039 (7)	0.0012 (7)
C34	0.0397 (8)	0.0325 (8)	0.0428 (8)	−0.0022 (6)	0.0100 (6)	0.0030 (6)
C35	0.0454 (8)	0.0351 (8)	0.0398 (8)	0.0023 (7)	0.0129 (7)	0.0083 (7)
C36	0.0449 (9)	0.0533 (10)	0.0542 (10)	−0.0025 (8)	0.0150 (8)	0.0075 (8)
C37	0.0516 (10)	0.0627 (12)	0.0719 (13)	0.0062 (9)	0.0295 (10)	0.0160 (10)
C38	0.0701 (13)	0.0600 (12)	0.0604 (12)	0.0077 (10)	0.0368 (10)	0.0079 (10)
C39	0.0636 (11)	0.0471 (10)	0.0393 (9)	0.0075 (8)	0.0228 (8)	0.0078 (7)
C40	0.0629 (11)	0.0618 (12)	0.0479 (10)	0.0086 (9)	0.0201 (9)	−0.0079 (9)
N1	0.0483 (8)	0.0476 (8)	0.0400 (8)	−0.0026 (6)	0.0021 (6)	0.0045 (6)
N2	0.0500 (8)	0.0452 (8)	0.0385 (7)	0.0026 (6)	0.0118 (6)	0.0039 (6)
O1	0.0480 (6)	0.0527 (7)	0.0404 (6)	0.0015 (5)	0.0181 (5)	−0.0076 (5)
O2	0.0388 (6)	0.0544 (7)	0.0406 (6)	−0.0086 (5)	−0.0007 (5)	−0.0098 (5)

Geometric parameters (Å, º) top

C1—O1	1.4286 (17)	C21—C22	1.529 (2)
C1—C2	1.525 (2)	C21—C28	1.533 (2)
C1—C8	1.538 (2)	C21—C34	1.550 (2)
C1—C14	1.553 (2)	C22—C27	1.381 (2)
C2—C7	1.387 (2)	C22—C23	1.399 (2)
C2—C3	1.393 (2)	C23—C24	1.379 (3)
C3—C4	1.388 (2)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.373 (3)
C4—C5	1.375 (3)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.378 (3)
C5—C6	1.363 (3)	C25—H25	0.9300
C5—H5	0.9300	C26—C27	1.385 (2)
C6—C7	1.389 (3)	C26—H26	0.9300
C6—H6	0.9300	C27—H27	0.9300
C7—H7	0.9300	C28—C29	1.387 (2)
C8—C9	1.387 (2)	C28—C33	1.403 (2)
C8—C13	1.388 (2)	C29—C30	1.396 (3)
C9—C10	1.398 (2)	C29—H29	0.9300
C9—H9	0.9300	C30—C31	1.392 (3)
C10—C11	1.365 (3)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.358 (3)
C11—C12	1.384 (3)	C31—H31	0.9300
C11—H11	0.9300	C32—C33	1.394 (2)
C12—C13	1.391 (3)	C32—H32	0.9300
C12—H12	0.9300	C33—H33	0.9300
C13—H13	0.9300	C34—C35	1.501 (2)
C14—C15	1.515 (2)	C34—H34A	0.9700
C14—H14A	0.9700	C34—H34B	0.9700
C14—H14B	0.9700	C35—N2	1.351 (2)
C15—N1	1.346 (2)	C35—C36	1.387 (2)
C15—C16	1.387 (2)	C36—C37	1.384 (3)
C16—C17	1.386 (3)	C36—H36	0.9300
C16—H16	0.9300	C37—C38	1.377 (3)
C17—C18	1.364 (3)	C37—H37	0.9300
C17—H17	0.9300	C38—C39	1.377 (3)
C18—C19	1.382 (3)	C38—H38	0.9300
C18—H18	0.9300	C39—N2	1.340 (2)
C19—N1	1.346 (2)	C39—C40	1.514 (3)
C19—C20	1.500 (3)	C40—H40A	0.9600
C20—H20A	0.9600	C40—H40B	0.9600
C20—H20B	0.9600	C40—H40C	0.9600
C20—H20C	0.9600	O1—H1A	0.96 (2)
C21—O2	1.4334 (17)	O2—H2A	0.96 (2)

O1—C1—C2	109.66 (11)	C22—C21—C28	111.41 (12)
O1—C1—C8	106.55 (11)	O2—C21—C34	109.08 (12)
C2—C1—C8	111.07 (12)	C22—C21—C34	108.18 (11)
O1—C1—C14	108.72 (12)	C28—C21—C34	112.34 (12)
C2—C1—C14	113.37 (12)	C27—C22—C23	118.02 (15)
C8—C1—C14	107.20 (12)	C27—C22—C21	123.47 (14)
C7—C2—C3	117.55 (15)	C23—C22—C21	118.48 (14)
C7—C2—C1	119.86 (13)	C24—C23—C22	120.83 (18)
C3—C2—C1	122.52 (14)	C24—C23—H23	119.6
C4—C3—C2	120.90 (16)	C22—C23—H23	119.6
C4—C3—H3	119.5	C25—C24—C23	120.24 (19)
C2—C3—H3	119.5	C25—C24—H24	119.9
C5—C4—C3	120.25 (17)	C23—C24—H24	119.9
C5—C4—H4	119.9	C24—C25—C26	119.75 (17)
C3—C4—H4	119.9	C24—C25—H25	120.1
C6—C5—C4	119.74 (17)	C26—C25—H25	120.1
C6—C5—H5	120.1	C25—C26—C27	120.15 (19)
C4—C5—H5	120.1	C25—C26—H26	119.9
C5—C6—C7	120.37 (18)	C27—C26—H26	119.9
C5—C6—H6	119.8	C22—C27—C26	121.00 (16)
C7—C6—H6	119.8	C22—C27—H27	119.5
C2—C7—C6	121.17 (16)	C26—C27—H27	119.5
C2—C7—H7	119.4	C29—C28—C33	117.78 (15)
C6—C7—H7	119.4	C29—C28—C21	119.76 (14)
C9—C8—C13	118.06 (15)	C33—C28—C21	122.37 (13)
C9—C8—C1	122.85 (13)	C28—C29—C30	120.78 (17)
C13—C8—C1	119.07 (14)	C28—C29—H29	119.6
C8—C9—C10	120.65 (16)	C30—C29—H29	119.6
C8—C9—H9	119.7	C31—C30—C29	119.95 (17)
C10—C9—H9	119.7	C31—C30—H30	120.0
C11—C10—C9	120.83 (19)	C29—C30—H30	120.0
C11—C10—H10	119.6	C32—C31—C30	120.22 (17)
C9—C10—H10	119.6	C32—C31—H31	119.9
C10—C11—C12	119.17 (17)	C30—C31—H31	119.9
C10—C11—H11	120.4	C31—C32—C33	120.01 (18)
C12—C11—H11	120.4	C31—C32—H32	120.0
C11—C12—C13	120.33 (18)	C33—C32—H32	120.0
C11—C12—H12	119.8	C32—C33—C28	121.25 (16)
C13—C12—H12	119.8	C32—C33—H33	119.4
C8—C13—C12	120.95 (18)	C28—C33—H33	119.4
C8—C13—H13	119.5	C35—C34—C21	115.16 (12)
C12—C13—H13	119.5	C35—C34—H34A	108.5
C15—C14—C1	114.95 (12)	C21—C34—H34A	108.5
C15—C14—H14A	108.5	C35—C34—H34B	108.5
C1—C14—H14A	108.5	C21—C34—H34B	108.5
C15—C14—H14B	108.5	H34A—C34—H34B	107.5
C1—C14—H14B	108.5	N2—C35—C36	122.03 (15)
H14A—C14—H14B	107.5	N2—C35—C34	115.57 (13)
N1—C15—C16	121.93 (15)	C36—C35—C34	122.35 (15)
N1—C15—C14	115.37 (13)	C37—C36—C35	118.10 (18)
C16—C15—C14	122.62 (15)	C37—C36—H36	121.0
C17—C16—C15	117.81 (18)	C35—C36—H36	121.0
C17—C16—H16	121.1	C38—C37—C36	119.67 (18)
C15—C16—H16	121.1	C38—C37—H37	120.2
C18—C17—C16	120.15 (19)	C36—C37—H37	120.2
C18—C17—H17	119.9	C37—C38—C39	119.50 (17)
C16—C17—H17	119.9	C37—C38—H38	120.2
C17—C18—C19	119.70 (18)	C39—C38—H38	120.2
C17—C18—H18	120.2	N2—C39—C38	121.49 (18)
C19—C18—H18	120.2	N2—C39—C40	115.73 (16)
N1—C19—C18	120.77 (18)	C38—C39—C40	122.77 (16)
N1—C19—C20	116.34 (18)	C39—C40—H40A	109.5
C18—C19—C20	122.87 (18)	C39—C40—H40B	109.5
C19—C20—H20A	109.5	H40A—C40—H40B	109.5
C19—C20—H20B	109.5	C39—C40—H40C	109.5
H20A—C20—H20B	109.5	H40A—C40—H40C	109.5
C19—C20—H20C	109.5	H40B—C40—H40C	109.5
H20A—C20—H20C	109.5	C19—N1—C15	119.63 (16)
H20B—C20—H20C	109.5	C39—N2—C35	119.21 (15)
O2—C21—C22	106.24 (11)	C1—O1—H1A	109.3 (11)
O2—C21—C28	109.39 (12)	C21—O2—H2A	109.5 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.96 (2)	1.89 (2)	2.724 (2)	144 (2)
O2—H2A···N2	0.96 (2)	1.92 (2)	2.718 (2)	139 (2)
C18—H18···O2ⁱ	0.93	2.70	3.518 (2)	147
C38—H38···O1ⁱⁱ	0.93	2.65	3.472 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO
M_r	289.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	13.466 (2), 8.022 (1), 30.220 (3)
β (°)	102.874 (3)
V (Å³)	3182.4 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.98, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	24109, 6247, 4901
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.116, 1.03
No. of reflections	6247
No. of parameters	405
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.96 (2)	1.89 (2)	2.724 (2)	144 (2)
O2—H2A···N2	0.96 (2)	1.92 (2)	2.718 (2)	139 (2)
C18—H18···O2ⁱ	0.93	2.70	3.518 (2)	146.5
C38—H38···O1ⁱⁱ	0.93	2.65	3.472 (2)	147.1

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

Acknowledgements

We thank the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant No. 07KJD150101) for financial support.

References

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