6-Allyl-8-meth­oxy-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

Zhu, J.; Ren, Z.-D.; Liu, Y.; Zhao, L.; Wu, Y.

doi:10.1107/S1600536811027474

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2056

doi:10.1107/S1600536811027474

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6-Allyl-8-methoxy-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

Jing Zhu,^a ^* Zhi-Dong Ren,^a Yang Liu,^a Lei Zhao ^a and Yong Wu ^a

^aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: jingzhuhaut@126.com

(Received 27 June 2011; accepted 8 July 2011; online 16 July 2011)

In the title compound, C₁₈H₁₉NO₂, the allyl group is disordered over two sets of sites [occupancy ratio 0.662 (4):0.338 (4)]. The dihedral angle between the phenyl and benzene rings is 87.44 (10)°. The oxazinane ring adopts a sofa conformation.

Related literature

For similar heterocyclic compounds, see: Chen et al. (2007 ); Kiskan et al. (2007 ); Liu et al. (2007 ); Ran & Gu (2011 ); Sawaryn et al. (2010 ); Su et al. (2005 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₉NO₂
M_r = 281.34
Triclinic, $[P \overline 1]$
a = 8.4087 (5) Å
b = 9.4852 (5) Å
c = 10.7735 (7) Å
α = 99.193 (5)°
β = 98.900 (5)°
γ = 115.476 (6)°
V = 741.30 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 291 K
0.20 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur, Eos, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO . Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.659, T_max = 1.000
5471 measured reflections
2644 independent reflections
2282 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.05
2644 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027474/bx2360sup1.cif

Supporting information file. DOI: 10.1107/S1600536811027474/bx2360Isup3.cml

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027474/bx2360Isup2.hkl

checkCIF report

Comment top

Benzo[e][1,3]oxazines, which can be cured via a thermal ring opening reaction to construct an analogous phenolic structure characterized by a Mannich base bridge (–CH2—NR—CH2), are an important class of heterocycles (Su et al., 2005, Kiskan et al., 2007; Liu et al., 2007, Ran & Gu, 2011, Sawaryn et al., 2010). The title compound (I) was prepared by reaction of aniline, formaldehyde and 4-allyl-2-methoxyphenol. We report here the crystal structure of (I) .

The molecular structure of title compound (I) is showing in Fig. 1. The dihedral angle between the phenyl and benzene rings is 87.44 (10)° and this value is longer than similar compound reported by Chen et al., 2007. The allyl group was refined using a disorder model with an occupancy ratio of 0.662 (4):0.338 (4). The oxazinane ring of the benzoxazine moiety adopts the sofa conformation, with the puckering parameters q₂= 0.3505 (16) Å and ϕ = 272.3 (3)° (Cremer & Pople, 1975) .

Related literature top

For similar heterocyclic compounds, see: Chen et al. (2007); Kiskan et al. (2007); Liu et al. (2007); Ran & Gu (2011); Sawaryn et al. (2010); Su et al. (2005). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Aniline (0.05 mol), formaldehyde (0.1 mol), 4-allyl-2-methoxyphenol (0.05 mol) and 1,4-dioxine (50 ml) were introduced into a 250 ml flask, and the mixtures were stirred at 60 °C for 5 h, then condensed by rotary evaporators (35 °C), a red mucus was got and set at 15 °C for a few hour. The title compound was precipitated out in the meantime and washed by methanol. Colourless crystals suitable for X-ray diffraction analysis were obtained by recrystallization from methanol. And then the crystal of title compound was mounted in inert oil and transferred to the cold gas stream of the diffractometer.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. Molecular structure of (I), with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major occupied component is shown.

6-Allyl-8-methoxy-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine top

Crystal data top

C₁₈H₁₉NO₂	Z = 2
M_r = 281.34	F(000) = 300
Triclinic, P1	D_x = 1.260 Mg m⁻³
a = 8.4087 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 9.4852 (5) Å	Cell parameters from 3645 reflections
c = 10.7735 (7) Å	θ = 4.3–71.9°
α = 99.193 (5)°	µ = 0.65 mm⁻¹
β = 98.900 (5)°	T = 291 K
γ = 115.476 (6)°	Prismatics, colourless
V = 741.30 (9) Å³	0.20 × 0.18 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur, Eos, Gemini diffractometer	2644 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2282 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 16.2312 pixels mm^-1	θ_max = 67.1°, θ_min = 4.3°
ω scans	h = −10→10
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010)	k = −11→8
T_min = 0.659, T_max = 1.000	l = −12→11
5471 measured reflections

Refinement top

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0696P)² + 0.1724P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2644 reflections	Δρ_max = 0.48 e Å⁻³
190 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (14)

Crystal data top

C₁₈H₁₉NO₂	γ = 115.476 (6)°
M_r = 281.34	V = 741.30 (9) Å³
Triclinic, P1	Z = 2
a = 8.4087 (5) Å	Cu Kα radiation
b = 9.4852 (5) Å	µ = 0.65 mm⁻¹
c = 10.7735 (7) Å	T = 291 K
α = 99.193 (5)°	0.20 × 0.18 × 0.18 mm
β = 98.900 (5)°

Data collection top

Oxford Diffraction Xcalibur, Eos, Gemini diffractometer	2644 independent reflections
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010)	2282 reflections with I > 2σ(I)
T_min = 0.659, T_max = 1.000	R_int = 0.015
5471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.48 e Å⁻³
2644 reflections	Δρ_min = −0.50 e Å⁻³
190 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	Occ. (<1)
O1	0.42456 (15)	0.62744 (13)	0.74629 (10)	0.0489 (3)
O2	0.70231 (17)	0.91501 (15)	0.80687 (12)	0.0603 (4)
N1	0.16240 (18)	0.42342 (15)	0.79032 (13)	0.0462 (3)
C1	−0.0068 (2)	0.5813 (2)	0.80579 (17)	0.0524 (4)
H1	0.0679	0.6433	0.8878	0.063*
C2	−0.1479 (3)	0.6089 (3)	0.7517 (2)	0.0664 (5)
H2	−0.1677	0.6888	0.7980	0.080*
C3	−0.2584 (3)	0.5198 (3)	0.6308 (2)	0.0721 (6)
H3	−0.3528	0.5391	0.5950	0.087*
C4	−0.2286 (3)	0.4014 (3)	0.5626 (2)	0.0708 (6)
H4	−0.3028	0.3410	0.4801	0.085*
C5	−0.0896 (2)	0.3719 (2)	0.61587 (17)	0.0579 (5)
H5	−0.0713	0.2911	0.5693	0.070*
C6	0.0235 (2)	0.46179 (18)	0.73834 (15)	0.0439 (4)
C7	0.3052 (2)	0.45678 (19)	0.72467 (17)	0.0494 (4)
H7A	0.2516	0.4097	0.6322	0.059*
H7B	0.3766	0.4053	0.7539	0.059*
C8	0.2421 (2)	0.4814 (2)	0.93066 (16)	0.0495 (4)
H8A	0.2835	0.4084	0.9594	0.059*
H8B	0.1492	0.4807	0.9743	0.059*
C9	0.4001 (2)	0.65000 (19)	0.96899 (15)	0.0443 (4)
C10	0.4830 (2)	0.71108 (19)	0.87442 (15)	0.0433 (4)
C11	0.6315 (2)	0.86659 (19)	0.90761 (16)	0.0475 (4)
C12	0.6934 (2)	0.9570 (2)	1.03462 (18)	0.0555 (4)
H12	0.7927	1.0595	1.0567	0.067*
C13	0.6105 (3)	0.8981 (2)	1.13087 (17)	0.0566 (4)
C14	0.4646 (2)	0.7445 (2)	1.09664 (16)	0.0517 (4)
H14	0.4085	0.7035	1.1599	0.062*
C15	0.6797 (5)	1.0036 (3)	1.2695 (2)	0.0958 (6)
H15A	0.7676	1.1113	1.2695	0.115*	0.662 (4)
H15B	0.5782	1.0117	1.2961	0.115*	0.662 (4)
H15C	0.8114	1.0521	1.2917	0.115*	0.338 (4)
H15D	0.6483	1.0908	1.2695	0.115*	0.338 (4)
C16	0.7611 (5)	0.9503 (4)	1.3628 (3)	0.0737 (8)	0.662 (4)
H16	0.8657	0.9456	1.3499	0.088*	0.662 (4)
C17	0.7103 (4)	0.9065 (3)	1.4652 (2)	0.0958 (6)
H17A	0.6068	0.9083	1.4840	0.115*	0.662 (4)
H17B	0.7776	0.8736	1.5192	0.115*	0.662 (4)
H17C	0.8326	0.9343	1.4744	0.115*	0.338 (4)
H17D	0.6501	0.8585	1.5244	0.115*	0.338 (4)
C18	0.8505 (3)	1.0730 (2)	0.8341 (2)	0.0700 (6)
H18A	0.8854	1.0930	0.7554	0.105*
H18B	0.9516	1.0816	0.8959	0.105*
H18C	0.8144	1.1509	0.8692	0.105*
C16A	0.6213 (10)	0.9354 (8)	1.3672 (6)	0.0737 (8)	0.338 (4)
H16A	0.4995	0.9041	1.3648	0.088*	0.338 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0500 (6)	0.0476 (6)	0.0440 (6)	0.0192 (5)	0.0114 (5)	0.0092 (5)
O2	0.0589 (7)	0.0502 (7)	0.0648 (8)	0.0165 (6)	0.0224 (6)	0.0160 (6)
N1	0.0484 (7)	0.0398 (7)	0.0461 (7)	0.0182 (6)	0.0075 (6)	0.0107 (5)
C1	0.0509 (9)	0.0496 (9)	0.0533 (9)	0.0213 (7)	0.0117 (7)	0.0117 (7)
C2	0.0639 (11)	0.0742 (13)	0.0799 (14)	0.0418 (10)	0.0281 (10)	0.0305 (10)
C3	0.0525 (11)	0.1021 (16)	0.0756 (13)	0.0392 (11)	0.0188 (10)	0.0464 (12)
C4	0.0531 (10)	0.0885 (15)	0.0530 (10)	0.0197 (10)	0.0013 (8)	0.0223 (10)
C5	0.0553 (10)	0.0554 (10)	0.0493 (9)	0.0174 (8)	0.0063 (8)	0.0086 (8)
C6	0.0414 (8)	0.0380 (7)	0.0461 (8)	0.0119 (6)	0.0106 (6)	0.0142 (6)
C7	0.0531 (9)	0.0434 (8)	0.0519 (9)	0.0244 (7)	0.0114 (7)	0.0085 (7)
C8	0.0511 (9)	0.0496 (9)	0.0475 (9)	0.0219 (7)	0.0091 (7)	0.0192 (7)
C9	0.0443 (8)	0.0465 (8)	0.0451 (8)	0.0246 (7)	0.0063 (6)	0.0143 (6)
C10	0.0429 (8)	0.0445 (8)	0.0443 (8)	0.0238 (7)	0.0069 (6)	0.0102 (6)
C11	0.0465 (8)	0.0436 (8)	0.0556 (9)	0.0235 (7)	0.0114 (7)	0.0144 (7)
C12	0.0540 (10)	0.0418 (8)	0.0602 (10)	0.0184 (7)	0.0027 (8)	0.0086 (7)
C13	0.0676 (11)	0.0496 (9)	0.0498 (9)	0.0309 (8)	0.0024 (8)	0.0066 (7)
C14	0.0618 (10)	0.0556 (10)	0.0444 (9)	0.0331 (8)	0.0108 (7)	0.0159 (7)
C15	0.1375 (17)	0.0678 (10)	0.0570 (9)	0.0373 (11)	0.0030 (10)	0.0026 (8)
C16	0.0783 (19)	0.0780 (18)	0.0525 (14)	0.0396 (17)	−0.0006 (14)	−0.0091 (13)
C17	0.1375 (17)	0.0678 (10)	0.0570 (9)	0.0373 (11)	0.0030 (10)	0.0026 (8)
C18	0.0596 (11)	0.0532 (10)	0.0888 (15)	0.0155 (9)	0.0242 (10)	0.0226 (10)
C16A	0.0783 (19)	0.0780 (18)	0.0525 (14)	0.0396 (17)	−0.0006 (14)	−0.0091 (13)

Geometric parameters (Å, º) top

O1—C7	1.4463 (19)	C10—C11	1.404 (2)
O1—C10	1.3716 (18)	C11—C12	1.378 (2)
O2—C11	1.367 (2)	C12—H12	0.9300
O2—C18	1.423 (2)	C12—C13	1.395 (3)
N1—C6	1.427 (2)	C13—C14	1.384 (3)
N1—C7	1.432 (2)	C13—C15	1.524 (3)
N1—C8	1.463 (2)	C14—H14	0.9300
C1—H1	0.9300	C15—H15A	0.9700
C1—C2	1.384 (3)	C15—H15B	0.9700
C1—C6	1.387 (2)	C15—H15C	0.9700
C2—H2	0.9300	C15—H15D	0.9700
C2—C3	1.368 (3)	C15—C16	1.408 (4)
C3—H3	0.9300	C15—C16A	1.368 (8)
C3—C4	1.379 (3)	C16—H16	0.9300
C4—H4	0.9300	C16—C17	1.308 (4)
C4—C5	1.378 (3)	C17—H17A	0.9300
C5—H5	0.9300	C17—H17B	0.9300
C5—C6	1.388 (2)	C17—H17C	0.9300
C7—H7A	0.9700	C17—H17D	0.9300
C7—H7B	0.9700	C17—C16A	1.332 (7)
C8—H8A	0.9700	C18—H18A	0.9600
C8—H8B	0.9700	C18—H18B	0.9600
C8—C9	1.511 (2)	C18—H18C	0.9600
C9—C10	1.386 (2)	C16A—H16A	0.9300
C9—C14	1.395 (2)

C10—O1—C7	113.65 (12)	C13—C14—C9	121.22 (16)
C11—O2—C18	117.67 (15)	C13—C14—H14	119.4
C6—N1—C7	115.33 (13)	C13—C15—H15A	108.3
C6—N1—C8	117.51 (13)	C13—C15—H15B	108.3
C7—N1—C8	109.17 (13)	C13—C15—H15C	107.5
C2—C1—H1	119.9	C13—C15—H15D	107.5
C2—C1—C6	120.30 (17)	H15A—C15—H15B	107.4
C6—C1—H1	119.9	H15A—C15—H15C	51.2
C1—C2—H2	119.6	H15A—C15—H15D	57.7
C3—C2—C1	120.71 (19)	H15B—C15—H15C	142.9
C3—C2—H2	119.6	H15B—C15—H15D	52.4
C2—C3—H3	120.3	H15C—C15—H15D	107.0
C2—C3—C4	119.46 (18)	C16—C15—C13	115.9 (2)
C4—C3—H3	120.3	C16—C15—H15A	108.3
C3—C4—H4	119.8	C16—C15—H15B	108.3
C5—C4—C3	120.37 (18)	C16—C15—H15C	63.0
C5—C4—H4	119.8	C16—C15—H15D	136.5
C4—C5—H5	119.7	C16A—C15—C13	119.2 (3)
C4—C5—C6	120.62 (18)	C16A—C15—H15A	132.4
C6—C5—H5	119.7	C16A—C15—H15B	61.8
C1—C6—N1	123.14 (14)	C16A—C15—H15C	107.5
C1—C6—C5	118.54 (16)	C16A—C15—H15D	107.5
C5—C6—N1	118.30 (15)	C16A—C15—C16	48.1 (3)
O1—C7—H7A	108.9	C15—C16—H16	115.5
O1—C7—H7B	108.9	C17—C16—C15	129.1 (3)
N1—C7—O1	113.26 (13)	C17—C16—H16	115.5
N1—C7—H7A	108.9	C16—C17—H17A	120.0
N1—C7—H7B	108.9	C16—C17—H17B	120.0
H7A—C7—H7B	107.7	C16—C17—H17C	70.0
N1—C8—H8A	109.1	C16—C17—H17D	167.1
N1—C8—H8B	109.1	C16—C17—C16A	50.8 (4)
N1—C8—C9	112.41 (13)	H17A—C17—H17B	120.0
H8A—C8—H8B	107.9	H17A—C17—H17C	159.0
C9—C8—H8A	109.1	H17A—C17—H17D	53.8
C9—C8—H8B	109.1	H17B—C17—H17C	53.8
C10—C9—C8	118.78 (14)	H17B—C17—H17D	67.4
C10—C9—C14	119.50 (15)	H17C—C17—H17D	120.0
C14—C9—C8	121.72 (15)	C16A—C17—H17A	69.9
O1—C10—C9	122.98 (14)	C16A—C17—H17B	167.4
O1—C10—C11	117.02 (14)	C16A—C17—H17C	120.0
C9—C10—C11	119.99 (15)	C16A—C17—H17D	120.0
O2—C11—C10	115.13 (14)	O2—C18—H18A	109.5
O2—C11—C12	125.52 (15)	O2—C18—H18B	109.5
C12—C11—C10	119.36 (16)	O2—C18—H18C	109.5
C11—C12—H12	119.3	H18A—C18—H18B	109.5
C11—C12—C13	121.45 (16)	H18A—C18—H18C	109.5
C13—C12—H12	119.3	H18B—C18—H18C	109.5
C12—C13—C15	119.89 (19)	C15—C16A—H16A	114.7
C14—C13—C12	118.48 (16)	C17—C16A—C15	130.5 (6)
C14—C13—C15	121.63 (19)	C17—C16A—H16A	114.7
C9—C14—H14	119.4

O1—C10—C11—O2	−1.0 (2)	C8—C9—C14—C13	179.36 (15)
O1—C10—C11—C12	178.79 (14)	C9—C10—C11—O2	−179.74 (13)
O2—C11—C12—C13	179.05 (15)	C9—C10—C11—C12	0.1 (2)
N1—C8—C9—C10	−17.6 (2)	C10—O1—C7—N1	47.99 (18)
N1—C8—C9—C14	162.77 (14)	C10—C9—C14—C13	−0.3 (2)
C1—C2—C3—C4	0.1 (3)	C10—C11—C12—C13	−0.7 (3)
C2—C1—C6—N1	−177.76 (15)	C11—C12—C13—C14	0.9 (3)
C2—C1—C6—C5	0.4 (2)	C11—C12—C13—C15	−178.27 (19)
C2—C3—C4—C5	0.4 (3)	C12—C13—C14—C9	−0.4 (3)
C3—C4—C5—C6	−0.6 (3)	C12—C13—C15—C16	−113.3 (3)
C4—C5—C6—N1	178.38 (16)	C12—C13—C15—C16A	−167.9 (4)
C4—C5—C6—C1	0.2 (3)	C13—C15—C16—C17	−117.6 (3)
C6—N1—C7—O1	71.23 (17)	C13—C15—C16A—C17	110.4 (6)
C6—N1—C8—C9	−87.32 (17)	C14—C9—C10—O1	−178.21 (13)
C6—C1—C2—C3	−0.5 (3)	C14—C9—C10—C11	0.4 (2)
C7—O1—C10—C9	−16.4 (2)	C14—C13—C15—C16	67.6 (4)
C7—O1—C10—C11	164.92 (13)	C14—C13—C15—C16A	13.0 (5)
C7—N1—C6—C1	−114.38 (17)	C15—C13—C14—C9	178.77 (18)
C7—N1—C6—C5	67.48 (18)	C15—C16—C17—C16A	10.4 (4)
C7—N1—C8—C9	46.45 (17)	C16—C15—C16A—C17	10.5 (4)
C8—N1—C6—C1	16.6 (2)	C16—C17—C16A—C15	−10.9 (4)
C8—N1—C6—C5	−161.52 (14)	C18—O2—C11—C10	178.62 (15)
C8—N1—C7—O1	−63.64 (17)	C18—O2—C11—C12	−1.2 (2)
C8—C9—C10—O1	2.1 (2)	C16A—C15—C16—C17	−10.5 (4)
C8—C9—C10—C11	−179.22 (13)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₂
M_r	281.34
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.4087 (5), 9.4852 (5), 10.7735 (7)
α, β, γ (°)	99.193 (5), 98.900 (5), 115.476 (6)
V (Å³)	741.30 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur, Eos, Gemini diffractometer
Absorption correction	Multi-scan CrysAlis PRO (Oxford Diffraction, 2010)
T_min, T_max	0.659, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5471, 2644, 2282
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.05
No. of reflections	2644
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.50

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Selected geometric parameters (Å, º) top

O1—C7	1.4463 (19)	N1—C6	1.427 (2)
O1—C10	1.3716 (18)	N1—C7	1.432 (2)
O2—C11	1.367 (2)	N1—C8	1.463 (2)
O2—C18	1.423 (2)

C10—O1—C7	113.65 (12)	C6—N1—C8	117.51 (13)
C6—N1—C7	115.33 (13)	C7—N1—C8	109.17 (13)

References

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