2-Butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Li, Y.H.; Zhao, M.M.; Zhang, Y.

doi:10.1107/S1600536808029383

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1972

doi:10.1107/S1600536808029383

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2-Butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Yong Hua Li,^a ^* Min Min Zhao ^a and Yuan Zhang ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: liyhnju@hotmail.com

(Received 20 August 2008; accepted 13 September 2008; online 20 September 2008)

In the title compound, C₂₈H₂₇NO, the oxazine ring adopts a half-chair conformation. The dihedral angles between the phenyl rings and the naphthyl ring system are 15.34 (1) and 76.51 (1)°.

Related literature

For general background on oxazine compounds, see: Barker et al. (2006 ); Ren et al. (2001 ); Petterson et al. (1990 ); Peglion et al. (1997 ). For related structures, see: Alfonsov et al. (2007 ); Ji et al. (2005 ).

Experimental

Crystal data

C₂₈H₂₇NO
M_r = 393.51
Triclinic, $[P \overline 1]$
a = 8.8959 (15) Å
b = 10.7589 (16) Å
c = 11.8401 (18) Å
α = 96.219 (1)°
β = 98.366 (2)°
γ = 97.274 (2)°
V = 1102.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.965, T_max = 0.977
10108 measured reflections
4302 independent reflections
2352 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.262
S = 1.02
4302 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029383/pv2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029383/pv2101Isup2.hkl

checkCIF report

Comment top

Continuing efforts have been made to synthesize oxazine compounds because they are widely used as antipsychotic agents (Barker et al., 2006), antimalarial agents (Ren et al., 2001) and serotonin, dopamine receptors agonists (Petterson et al., 1990; Peglion et al., 1997). We have prepared a novel compound, 2-butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine, (I), by the reaction of 2-naphthol, benzaldehyde and n-butylamine. In this paper, we present the synthesis and crystal structure of (I). The structures of some closely related compounds have been reported (Alfonsov et al., 2007; Ji et al. 2005).

In the molecule of the title compound (Fig. 1), the oxazine ring adopts a half chair conformation. An intra-molecular interaction, C17—H15···O1, is observed in the crystal structure, but no inter-molecular hydrogen bonding was present. The dihedral angle between the C16–C21 phenyl ring and naphthyl system is 15.34 (1)° and the dihedral angle between the C23–C28 phenyl ring and naphthyl system is 76.51 (1)°.

Related literature top

For general background on oxazine compounds, see: Barker et al. (2006); Ren et al. (2001); Petterson et al. (1990); Peglion et al. (1997). For related structures, see: Alfonsov et al. (2007); Ji et al. (2005).

Experimental top

The title compound was one of the products of the reaction between 2-naphthol, n-butylamine and an excess amount of benzaldehyde. Benzaldehyde (22.05 g, 0.208 mol) was added to a solution of 2-naphthol (15 g, 0.104 mol) in 20 ml 95% ethanol. n-Butylamine (7.65 g, 0.104 mol) was added dropwise with cooling to 273 K to this solution. The mixture was stirred at room temperature for 6 days and the precipitate was filtrated and washed with a small amount of 95% ethanol. The title compound was isolated using column chromatography (petroleum ether: ethyl acetate - 30:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of an ethanol solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-Butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine top

Crystal data top

C₂₈H₂₇NO	Z = 2
M_r = 393.51	F(000) = 420
Triclinic, P1	D_x = 1.185 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8959 (15) Å	Cell parameters from 2254 reflections
b = 10.7589 (16) Å	θ = 2.3–27.5°
c = 11.8401 (18) Å	µ = 0.07 mm⁻¹
α = 96.219 (1)°	T = 293 K
β = 98.366 (2)°	Prism, colourless
γ = 97.274 (2)°	0.20 × 0.18 × 0.15 mm
V = 1102.8 (3) Å³

Data collection top

Rigaku SCXmini diffractometer	4302 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scan	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.965, T_max = 0.977	l = −14→14
10108 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.262	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1501P)²] where P = (F_o² + 2F_c²)/3
4302 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₈H₂₇NO	γ = 97.274 (2)°
M_r = 393.51	V = 1102.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.8959 (15) Å	Mo Kα radiation
b = 10.7589 (16) Å	µ = 0.07 mm⁻¹
c = 11.8401 (18) Å	T = 293 K
α = 96.219 (1)°	0.20 × 0.18 × 0.15 mm
β = 98.366 (2)°

Data collection top

Rigaku SCXmini diffractometer	4302 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2352 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.977	R_int = 0.041
10108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.262	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
4302 reflections	Δρ_min = −0.34 e Å⁻³
272 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 > 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	−0.0487 (3)	0.6705 (3)	0.1444 (2)	0.0520 (7)
C10	−0.0728 (3)	0.7223 (3)	0.2512 (2)	0.0486 (7)
C16	0.3447 (3)	0.8083 (3)	0.1275 (2)	0.0489 (7)
C9	−0.2156 (3)	0.6833 (3)	0.2883 (3)	0.0551 (7)
C11	0.0504 (3)	0.8228 (3)	0.3234 (2)	0.0522 (7)
H5	−0.0016	0.8926	0.3505	0.063*
C2	−0.1621 (3)	0.5819 (3)	0.0713 (3)	0.0604 (8)
H6	−0.1439	0.5486	−0.0004	0.073*
C22	0.2099 (3)	0.7704 (3)	0.1862 (2)	0.0505 (7)
H7	0.2422	0.7124	0.2402	0.061*
C4	−0.3288 (3)	0.5932 (3)	0.2146 (3)	0.0599 (8)
C23	0.1350 (3)	0.7789 (3)	0.4296 (2)	0.0517 (7)
C12	0.1042 (3)	0.9693 (3)	0.1822 (2)	0.0571 (7)
H10A	−0.0048	0.9450	0.1546	0.069*
H10B	0.1561	0.9711	0.1156	0.069*
C21	0.4792 (3)	0.8709 (3)	0.1948 (3)	0.0621 (8)
H11	0.4811	0.8926	0.2732	0.074*
C3	−0.2976 (3)	0.5457 (3)	0.1064 (3)	0.0689 (9)
H12	−0.3719	0.4880	0.0575	0.083*
C8	−0.2484 (4)	0.7299 (3)	0.3967 (3)	0.0677 (9)
H13	−0.1762	0.7890	0.4460	0.081*
C24	0.1235 (3)	0.6555 (3)	0.4499 (2)	0.0560 (7)
H14	0.0583	0.5941	0.3977	0.067*
C17	0.3449 (4)	0.7784 (3)	0.0112 (3)	0.0641 (8)
H15	0.2562	0.7370	−0.0362	0.077*
C5	−0.4699 (3)	0.5539 (4)	0.2525 (4)	0.0777 (10)
H16	−0.5451	0.4959	0.2046	0.093*
C13	0.1311 (4)	1.1005 (3)	0.2498 (3)	0.0712 (9)
H17A	0.0864	1.0966	0.3196	0.085*
H17B	0.2408	1.1267	0.2724	0.085*
C19	0.6094 (4)	0.8710 (3)	0.0332 (3)	0.0733 (10)
H18	0.6979	0.8914	0.0018	0.088*
C18	0.4781 (4)	0.8101 (4)	−0.0357 (3)	0.0799 (10)
H19	0.4773	0.7898	−0.1141	0.096*
C7	−0.3862 (4)	0.6891 (4)	0.4304 (3)	0.0834 (11)
H20	−0.4062	0.7209	0.5021	0.100*
C20	0.6101 (4)	0.9016 (3)	0.1482 (3)	0.0717 (9)
H21	0.6991	0.9434	0.1952	0.086*
C14	0.0657 (5)	1.1976 (4)	0.1856 (3)	0.0914 (12)
H4	−0.0446	1.1733	0.1661	0.110*
H22B	0.1067	1.1986	0.1141	0.110*
C25	0.2064 (4)	0.6200 (4)	0.5459 (3)	0.0716 (9)
H23	0.1957	0.5354	0.5574	0.086*
C6	−0.4955 (4)	0.6004 (4)	0.3579 (4)	0.0896 (12)
H24	−0.5874	0.5726	0.3821	0.108*
C28	0.2381 (4)	0.8682 (3)	0.5083 (3)	0.0834 (11)
H25	0.2524	0.9524	0.4960	0.100*
C26	0.3032 (5)	0.7066 (4)	0.6236 (3)	0.0845 (11)
H26	0.3579	0.6821	0.6885	0.101*
C27	0.3192 (5)	0.8298 (4)	0.6054 (3)	0.1023 (14)
H27	0.3853	0.8896	0.6585	0.123*
C15	0.0978 (6)	1.3295 (4)	0.2499 (4)	0.1108 (15)
H3	0.0502	1.3314	0.3177	0.166*
H2	0.0570	1.3872	0.2013	0.166*
H1	0.2067	1.3539	0.2716	0.166*
N1	0.1605 (2)	0.8740 (2)	0.25219 (18)	0.0489 (6)
O1	0.0848 (2)	0.69988 (18)	0.10138 (16)	0.0578 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0460 (15)	0.0516 (17)	0.0593 (16)	0.0120 (12)	0.0086 (13)	0.0048 (13)
C10	0.0449 (14)	0.0492 (16)	0.0540 (15)	0.0082 (11)	0.0119 (12)	0.0108 (12)
C16	0.0508 (15)	0.0450 (15)	0.0544 (15)	0.0123 (11)	0.0143 (13)	0.0080 (12)
C9	0.0489 (16)	0.0567 (18)	0.0652 (18)	0.0162 (13)	0.0125 (14)	0.0187 (14)
C11	0.0547 (16)	0.0477 (16)	0.0566 (16)	0.0118 (12)	0.0161 (13)	0.0024 (12)
C2	0.0490 (17)	0.0607 (19)	0.0671 (18)	0.0078 (13)	0.0032 (14)	−0.0033 (15)
C22	0.0513 (16)	0.0473 (16)	0.0521 (15)	0.0100 (12)	0.0067 (13)	0.0010 (12)
C4	0.0422 (15)	0.0596 (19)	0.082 (2)	0.0098 (13)	0.0107 (15)	0.0226 (16)
C23	0.0565 (16)	0.0527 (17)	0.0462 (14)	0.0079 (12)	0.0123 (13)	0.0020 (12)
C12	0.0645 (17)	0.0514 (17)	0.0589 (17)	0.0157 (13)	0.0144 (14)	0.0083 (13)
C21	0.0573 (18)	0.066 (2)	0.0652 (18)	0.0055 (14)	0.0170 (15)	0.0125 (15)
C3	0.0478 (17)	0.060 (2)	0.093 (2)	0.0083 (14)	−0.0060 (17)	0.0046 (17)
C8	0.0602 (18)	0.075 (2)	0.075 (2)	0.0158 (15)	0.0238 (16)	0.0203 (17)
C24	0.0505 (16)	0.0596 (19)	0.0590 (17)	0.0018 (13)	0.0138 (13)	0.0127 (14)
C17	0.0610 (18)	0.070 (2)	0.0643 (18)	0.0091 (15)	0.0206 (15)	0.0082 (15)
C5	0.0448 (17)	0.081 (2)	0.112 (3)	0.0058 (15)	0.0152 (19)	0.033 (2)
C13	0.090 (2)	0.0544 (19)	0.073 (2)	0.0154 (16)	0.0162 (18)	0.0122 (15)
C19	0.063 (2)	0.071 (2)	0.098 (3)	0.0118 (16)	0.041 (2)	0.0249 (19)
C18	0.094 (3)	0.088 (3)	0.067 (2)	0.018 (2)	0.038 (2)	0.0108 (18)
C7	0.068 (2)	0.107 (3)	0.094 (3)	0.025 (2)	0.044 (2)	0.036 (2)
C20	0.0578 (19)	0.069 (2)	0.090 (2)	0.0049 (15)	0.0180 (18)	0.0160 (18)
C14	0.125 (3)	0.066 (2)	0.097 (3)	0.034 (2)	0.033 (3)	0.024 (2)
C25	0.070 (2)	0.082 (2)	0.069 (2)	0.0103 (17)	0.0176 (18)	0.0276 (18)
C6	0.054 (2)	0.112 (3)	0.118 (3)	0.020 (2)	0.029 (2)	0.048 (3)
C28	0.111 (3)	0.062 (2)	0.068 (2)	0.0097 (19)	−0.001 (2)	−0.0060 (17)
C26	0.101 (3)	0.098 (3)	0.057 (2)	0.021 (2)	0.008 (2)	0.021 (2)
C27	0.130 (4)	0.096 (3)	0.064 (2)	0.018 (3)	−0.024 (2)	−0.015 (2)
C15	0.165 (4)	0.064 (3)	0.117 (3)	0.037 (3)	0.050 (3)	0.012 (2)
N1	0.0543 (13)	0.0453 (13)	0.0494 (12)	0.0119 (10)	0.0120 (10)	0.0063 (10)
O1	0.0514 (11)	0.0605 (13)	0.0576 (12)	0.0002 (9)	0.0120 (9)	−0.0051 (9)

Geometric parameters (Å, º) top

C1—O1	1.373 (3)	C24—C25	1.379 (4)
C1—C10	1.383 (4)	C24—H14	0.9300
C1—C2	1.414 (4)	C17—C18	1.399 (4)
C10—C9	1.432 (4)	C17—H15	0.9300
C10—C11	1.526 (4)	C5—C6	1.355 (5)
C16—C17	1.379 (4)	C5—H16	0.9300
C16—C21	1.386 (4)	C13—C14	1.485 (5)
C16—C22	1.506 (4)	C13—H17A	0.9700
C9—C8	1.411 (4)	C13—H17B	0.9700
C9—C4	1.425 (4)	C19—C20	1.364 (5)
C11—N1	1.477 (3)	C19—C18	1.368 (5)
C11—C23	1.520 (4)	C19—H18	0.9300
C11—H5	0.9800	C18—H19	0.9300
C2—C3	1.356 (4)	C7—C6	1.392 (5)
C2—H6	0.9300	C7—H20	0.9300
C22—N1	1.443 (3)	C20—H21	0.9300
C22—O1	1.456 (3)	C14—C15	1.508 (5)
C22—H7	0.9800	C14—H4	0.9700
C4—C3	1.406 (5)	C14—H22B	0.9700
C4—C5	1.424 (4)	C25—C26	1.356 (5)
C23—C24	1.369 (4)	C25—H23	0.9300
C23—C28	1.402 (4)	C6—H24	0.9300
C12—N1	1.477 (3)	C28—C27	1.396 (5)
C12—C13	1.519 (4)	C28—H25	0.9300
C12—H10A	0.9700	C26—C27	1.358 (6)
C12—H10B	0.9700	C26—H26	0.9300
C21—C20	1.379 (4)	C27—H27	0.9300
C21—H11	0.9300	C15—H3	0.9600
C3—H12	0.9300	C15—H2	0.9600
C8—C7	1.378 (4)	C15—H1	0.9600
C8—H13	0.9300

O1—C1—C10	123.4 (2)	C18—C17—H15	119.8
O1—C1—C2	115.1 (2)	C6—C5—C4	120.4 (4)
C10—C1—C2	121.5 (3)	C6—C5—H16	119.8
C1—C10—C9	118.7 (3)	C4—C5—H16	119.8
C1—C10—C11	119.1 (2)	C14—C13—C12	114.1 (3)
C9—C10—C11	122.1 (2)	C14—C13—H17A	108.7
C17—C16—C21	117.9 (3)	C12—C13—H17A	108.7
C17—C16—C22	123.8 (3)	C14—C13—H17B	108.7
C21—C16—C22	118.3 (2)	C12—C13—H17B	108.7
C8—C9—C4	118.2 (3)	H17A—C13—H17B	107.6
C8—C9—C10	122.3 (3)	C20—C19—C18	119.7 (3)
C4—C9—C10	119.4 (3)	C20—C19—H18	120.1
N1—C11—C23	110.4 (2)	C18—C19—H18	120.1
N1—C11—C10	110.7 (2)	C19—C18—C17	120.4 (3)
C23—C11—C10	114.3 (2)	C19—C18—H19	119.8
N1—C11—H5	107.0	C17—C18—H19	119.8
C23—C11—H5	107.0	C8—C7—C6	120.3 (4)
C10—C11—H5	107.0	C8—C7—H20	119.8
C3—C2—C1	119.6 (3)	C6—C7—H20	119.8
C3—C2—H6	120.2	C19—C20—C21	120.1 (3)
C1—C2—H6	120.2	C19—C20—H21	120.0
N1—C22—O1	111.8 (2)	C21—C20—H21	120.0
N1—C22—C16	114.3 (2)	C13—C14—C15	114.6 (4)
O1—C22—C16	109.3 (2)	C13—C14—H4	108.6
N1—C22—H7	107.0	C15—C14—H4	108.6
O1—C22—H7	107.0	C13—C14—H22B	108.6
C16—C22—H7	107.0	C15—C14—H22B	108.6
C3—C4—C5	122.0 (3)	H4—C14—H22B	107.6
C3—C4—C9	118.9 (3)	C26—C25—C24	120.9 (3)
C5—C4—C9	119.2 (3)	C26—C25—H23	119.5
C24—C23—C28	117.5 (3)	C24—C25—H23	119.5
C24—C23—C11	123.8 (2)	C5—C6—C7	121.0 (3)
C28—C23—C11	118.6 (3)	C5—C6—H24	119.5
N1—C12—C13	112.2 (2)	C7—C6—H24	119.5
N1—C12—H10A	109.2	C27—C28—C23	119.6 (3)
C13—C12—H10A	109.2	C27—C28—H25	120.2
N1—C12—H10B	109.2	C23—C28—H25	120.2
C13—C12—H10B	109.2	C25—C26—C27	119.1 (3)
H10A—C12—H10B	107.9	C25—C26—H26	120.4
C20—C21—C16	121.6 (3)	C27—C26—H26	120.4
C20—C21—H11	119.2	C26—C27—C28	121.2 (4)
C16—C21—H11	119.2	C26—C27—H27	119.4
C2—C3—C4	121.8 (3)	C28—C27—H27	119.4
C2—C3—H12	119.1	C14—C15—H3	109.5
C4—C3—H12	119.1	C14—C15—H2	109.5
C7—C8—C9	120.9 (3)	H3—C15—H2	109.5
C7—C8—H13	119.6	C14—C15—H1	109.5
C9—C8—H13	119.6	H3—C15—H1	109.5
C23—C24—C25	121.6 (3)	H2—C15—H1	109.5
C23—C24—H14	119.2	C22—N1—C11	109.0 (2)
C25—C24—H14	119.2	C22—N1—C12	113.8 (2)
C16—C17—C18	120.3 (3)	C11—N1—C12	113.8 (2)
C16—C17—H15	119.8	C1—O1—C22	113.8 (2)

O1—C1—C10—C9	−179.0 (2)	C11—C23—C24—C25	178.0 (3)
C2—C1—C10—C9	0.9 (4)	C21—C16—C17—C18	0.5 (5)
O1—C1—C10—C11	3.4 (4)	C22—C16—C17—C18	−176.0 (3)
C2—C1—C10—C11	−176.7 (2)	C3—C4—C5—C6	179.2 (3)
C1—C10—C9—C8	178.9 (3)	C9—C4—C5—C6	−0.8 (5)
C11—C10—C9—C8	−3.6 (4)	N1—C12—C13—C14	−175.6 (3)
C1—C10—C9—C4	−0.3 (4)	C20—C19—C18—C17	−0.5 (5)
C11—C10—C9—C4	177.2 (2)	C16—C17—C18—C19	0.0 (5)
C1—C10—C11—N1	15.7 (3)	C9—C8—C7—C6	0.2 (5)
C9—C10—C11—N1	−161.8 (2)	C18—C19—C20—C21	0.3 (5)
C1—C10—C11—C23	−109.8 (3)	C16—C21—C20—C19	0.2 (5)
C9—C10—C11—C23	72.7 (3)	C12—C13—C14—C15	−177.4 (3)
O1—C1—C2—C3	179.4 (2)	C23—C24—C25—C26	−0.3 (5)
C10—C1—C2—C3	−0.5 (4)	C4—C5—C6—C7	1.2 (6)
C17—C16—C22—N1	−126.3 (3)	C8—C7—C6—C5	−0.9 (6)
C21—C16—C22—N1	57.3 (3)	C24—C23—C28—C27	−2.6 (5)
C17—C16—C22—O1	−0.2 (4)	C11—C23—C28—C27	−178.9 (3)
C21—C16—C22—O1	−176.6 (2)	C24—C25—C26—C27	−0.6 (6)
C8—C9—C4—C3	−179.9 (3)	C25—C26—C27—C28	−0.1 (7)
C10—C9—C4—C3	−0.6 (4)	C23—C28—C27—C26	1.8 (6)
C8—C9—C4—C5	0.1 (4)	O1—C22—N1—C11	66.5 (3)
C10—C9—C4—C5	179.4 (3)	C16—C22—N1—C11	−168.7 (2)
N1—C11—C23—C24	−114.6 (3)	O1—C22—N1—C12	−61.7 (3)
C10—C11—C23—C24	11.1 (4)	C16—C22—N1—C12	63.1 (3)
N1—C11—C23—C28	61.4 (3)	C23—C11—N1—C22	79.0 (3)
C10—C11—C23—C28	−172.9 (3)	C10—C11—N1—C22	−48.7 (3)
C17—C16—C21—C20	−0.6 (4)	C23—C11—N1—C12	−152.9 (2)
C22—C16—C21—C20	176.0 (3)	C10—C11—N1—C12	79.5 (3)
C1—C2—C3—C4	−0.5 (5)	C13—C12—N1—C22	−150.4 (3)
C5—C4—C3—C2	−179.0 (3)	C13—C12—N1—C11	84.0 (3)
C9—C4—C3—C2	1.1 (5)	C10—C1—O1—C22	11.7 (4)
C4—C9—C8—C7	0.2 (4)	C2—C1—O1—C22	−168.2 (2)
C10—C9—C8—C7	−179.1 (3)	N1—C22—O1—C1	−47.0 (3)
C28—C23—C24—C25	1.9 (4)	C16—C22—O1—C1	−174.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H15···O1	0.93	2.42	2.762 (4)	102

Experimental details

Crystal data
Chemical formula	C₂₈H₂₇NO
M_r	393.51
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8959 (15), 10.7589 (16), 11.8401 (18)
α, β, γ (°)	96.219 (1), 98.366 (2), 97.274 (2)
V (Å³)	1102.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.965, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	10108, 4302, 2352
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.262, 1.02
No. of reflections	4302
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H15···O1	0.93	2.42	2.762 (4)	102

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Yong-Hua Li.

References

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