8-Meth­oxy-3-methyl-3,4-di­hydro-2H-1,3-benzoxazine

Zhu, J.; Yang, X.-X.; Xu, L.-Y.; Ren, Z.-D.; Qu, L.-B.

doi:10.1107/S1600536813026706

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1619

doi:10.1107/S1600536813026706

Open

access

8-Methoxy-3-methyl-3,4-dihydro-2H-1,3-benzoxazine

Jing Zhu,^a ^* Xiang-Xiang Yang,^a Long-Yu Xu,^a Zhi-Dong Ren ^a and Ling-Bo Qu ^a

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

(Received 13 September 2013; accepted 28 September 2013; online 5 October 2013)

The title compound, C₁₀H₁₃NO₂, crystallizes with two crystallographically independent molecules of similar geometry in the asymmetric unit; the six-membered oxazine rings adopts a half-chair conformation. Neither hydrogen bonds nor π–π interactions are observed in the crystal structure.

CCDC reference: 963639

Related literature

For the synthesis and applications of 1,3-benzoxazines, see: Holly & Cope (1944 ); Gu et al. (1998 ); Zheng et al. (2011 ); Rimdusit & Ishida (2000 ); Stewart (2009 ); Ning & Ishida (1994 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₀H₁₃NO₂
M_r = 179.21
Monoclinic, P 2₁ /c
a = 23.4234 (14) Å
b = 5.0054 (3) Å
c = 15.9408 (10) Å
β = 97.210 (6)°
V = 1854.2 (2) Å³
Z = 8
Cu Kα radiation
μ = 0.73 mm⁻¹
T = 291 K
0.22 × 0.20 × 0.18 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.783, T_max = 1.000
6857 measured reflections
3281 independent reflections
2471 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.02
3281 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); 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

CCDC reference: 963639

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813026706/rz5083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026706/rz5083Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026706/rz5083Isup3.cml

checkCIF report

Comment top

Benzo[e][1,3]oxazines, which are synthesized by an amine, a phenolic compound and formaldehyde via Mannich reaction (Holly & Cope, 1944), are a useful class of heterocyclic compounds. They can be cured via thermal ring-opening polymerization to construct a novel class of thermosetting resins called polybenzoxazins (Ning & Ishida, 1994). Polybenzoxazines have been widely used as automobile braking materials (Gu et al., 1998), copper clad laminates (Zheng et al., 2011), electronic packaging materials (Rimdusit & Ishida, 2000), aircraft cabin sidewalls (Stewart, 2009). The title compound was prepared by reaction of 2-methoxyphenol, formaldehyde and methylamine and its crystal structure is described herein.

The asymmetric unit of the title compound consists of two crystallographically independent molecules of similar geometry (Fig. 1). In both molecules the six-membered oxazine rings adopt a half-chair conformation, with atoms N1, C1 and N1', C1' displaced on opposite sides of the C2-C4/O1 (r.m.s deviation 0.0017 Å) and C2'-C4'/O1' (r.m.s deviation 0.0024 Å) mean planes by 0.4941 (15), 0.2019 (17) Å and 0.3664 (16), 0.351 (2) Å, respectively. The puckering parameters (Cremer & Pople, 1975) are Q = 0.4664 (16) Å, θ = 129.48 (19)°, ϕ = -75.7 (2)° for ring O1/C1/N1/C2–C4, and Q = 0.4722 (17) Å, θ = 128.97 (18)°, ϕ = -89.0 (3)° for ring O1'/C1'/N1'/C2'–C4'. In the crystal structure, no hydrogen bonding or π–π stacking interactions are observed.

Related literature top

For the synthesis and applications of 1,3-benzoxazines, see: Holly & Cope (1944); Gu et al. (1998); Zheng et al. (2011); Rimdusit & Ishida (2000); Stewart (2009); Ning & Ishida (1994). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Methylamine (40 wt% in water; 3.9 g, 0.05 mol), formaldehyde (37% wt in water; 8.1 g, 0.1 mol), 4-methoxyphenol (6.2 g, 0.05 mol) and 1, 4-dioxine (50 ml) were added to a 250 ml flask equipped with a condenser. The mixture was stirred at 90 °C for 5 h. After condensed by rotary evaporator, a yellowish-brown viscous liquid was obtained and set at room temperature for a few hours. After washing several times with methanol, a yellowish powder was precipitated. Anhydrous ether was used to dissolve the powder, and colourless crystals suitable for X-ray diffraction analysis were obtained by slow evoporation of the solvent.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Dolomanov et al., 2009).

Figures top

Fig. 1. The asymmetric unit of the title complound with displacement ellipsoids drawn at the 50% probability level.

8-Methoxy-3-methyl-3,4-dihydro-2H-1,3-benzoxazine top

Crystal data top

C₁₀H₁₃NO₂	F(000) = 768
M_r = 179.21	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 2369 reflections
a = 23.4234 (14) Å	θ = 3.2–66.9°
b = 5.0054 (3) Å	µ = 0.73 mm⁻¹
c = 15.9408 (10) Å	T = 291 K
β = 97.210 (6)°	Prism, colourless
V = 1854.2 (2) Å³	0.22 × 0.20 × 0.18 mm
Z = 8

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3281 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2471 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 16.2312 pixels mm^-1	θ_max = 67.1°, θ_min = 3.8°
ω scans	h = −19→27
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −3→5
T_min = 0.783, T_max = 1.000	l = −18→19
6857 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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0524P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3281 reflections	Δρ_max = 0.15 e Å⁻³
240 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0041 (3)

Crystal data top

C₁₀H₁₃NO₂	V = 1854.2 (2) Å³
M_r = 179.21	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 23.4234 (14) Å	µ = 0.73 mm⁻¹
b = 5.0054 (3) Å	T = 291 K
c = 15.9408 (10) Å	0.22 × 0.20 × 0.18 mm
β = 97.210 (6)°

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3281 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2471 reflections with I > 2σ(I)
T_min = 0.783, T_max = 1.000	R_int = 0.030
6857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
3281 reflections	Δρ_min = −0.16 e Å⁻³
240 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
O1	0.93754 (5)	0.7027 (2)	0.81029 (8)	0.0481 (3)
O2	0.93639 (5)	1.0466 (3)	0.93130 (8)	0.0507 (3)
N1	0.89328 (8)	0.5131 (3)	0.67831 (9)	0.0538 (4)
C1	0.93598 (8)	0.4853 (3)	0.74936 (12)	0.0526 (4)
H1A	0.9734	0.4725	0.7294	0.063*
H1B	0.9293	0.3192	0.7779	0.063*
C2	0.83649 (9)	0.5122 (4)	0.70753 (12)	0.0549 (5)
H2A	0.8282	0.3343	0.7268	0.066*
H2B	0.8075	0.5574	0.6607	0.066*
C3	0.83340 (7)	0.7092 (3)	0.77871 (10)	0.0429 (4)
C4	0.88444 (7)	0.7904 (3)	0.82559 (10)	0.0384 (3)
C5	0.88378 (7)	0.9799 (3)	0.89037 (9)	0.0395 (3)
C6	0.83181 (8)	1.0838 (4)	0.90755 (11)	0.0498 (4)
H6	0.8309	1.2096	0.9503	0.060*
C7	0.78089 (8)	1.0000 (4)	0.86090 (12)	0.0566 (5)
H7	0.7460	1.0694	0.8729	0.068*
C8	0.78165 (8)	0.8159 (4)	0.79739 (12)	0.0540 (5)
H8	0.7472	0.7620	0.7665	0.065*
C9	0.90299 (11)	0.7484 (4)	0.62759 (12)	0.0672 (6)
H9A	0.8977	0.9070	0.6595	0.101*
H9B	0.8761	0.7481	0.5769	0.101*
H9C	0.9415	0.7445	0.6131	0.101*
C10	0.93882 (9)	1.2585 (4)	0.99146 (12)	0.0551 (5)
H10D	0.9778	1.2823	1.0170	0.083*
H10E	0.9150	1.2153	1.0343	0.083*
H10F	0.9253	1.4206	0.9635	0.083*
O1'	0.33443 (5)	0.5282 (3)	0.32961 (8)	0.0572 (4)
O2'	0.28466 (6)	0.1922 (3)	0.42062 (9)	0.0659 (4)
N1'	0.41648 (7)	0.7858 (3)	0.30046 (10)	0.0520 (4)
C1'	0.35547 (8)	0.7584 (4)	0.28753 (13)	0.0590 (5)
H1'A	0.3430	0.7444	0.2273	0.071*
H1'B	0.3383	0.9184	0.3078	0.071*
C2'	0.43450 (8)	0.8338 (4)	0.39037 (12)	0.0521 (4)
H2'A	0.4257	1.0171	0.4037	0.063*
H2'B	0.4759	0.8107	0.4020	0.063*
C3'	0.40554 (7)	0.6489 (3)	0.44663 (11)	0.0435 (4)
C4'	0.35742 (7)	0.5065 (3)	0.41245 (10)	0.0426 (4)
C5'	0.33050 (7)	0.3264 (4)	0.46242 (11)	0.0467 (4)
C6'	0.35111 (8)	0.2984 (4)	0.54686 (12)	0.0547 (5)
H6'	0.3334	0.1806	0.5806	0.066*
C7'	0.39836 (9)	0.4464 (4)	0.58138 (12)	0.0622 (5)
H7'	0.4118	0.4299	0.6386	0.075*
C8'	0.42559 (8)	0.6174 (4)	0.53176 (12)	0.0566 (5)
H8'	0.4577	0.7129	0.5555	0.068*
C9'	0.44587 (9)	0.5579 (4)	0.26797 (13)	0.0611 (5)
H9'A	0.4335	0.5381	0.2086	0.092*
H9'B	0.4367	0.3986	0.2971	0.092*
H9'C	0.4867	0.5870	0.2769	0.092*
C10'	0.25623 (10)	0.0001 (5)	0.46693 (16)	0.0750 (7)
H10A	0.2276	−0.0919	0.4292	0.113*
H10B	0.2381	0.0892	0.5099	0.113*
H10C	0.2839	−0.1262	0.4929	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (6)	0.0478 (7)	0.0533 (7)	0.0041 (5)	0.0126 (5)	−0.0065 (5)
O2	0.0476 (6)	0.0544 (8)	0.0491 (7)	−0.0022 (5)	0.0019 (5)	−0.0106 (5)
N1	0.0802 (11)	0.0369 (8)	0.0467 (8)	−0.0029 (7)	0.0177 (7)	−0.0041 (6)
C1	0.0652 (11)	0.0365 (9)	0.0600 (11)	0.0048 (8)	0.0233 (9)	−0.0010 (8)
C2	0.0696 (11)	0.0432 (10)	0.0512 (10)	−0.0098 (9)	0.0047 (8)	−0.0056 (8)
C3	0.0495 (9)	0.0367 (9)	0.0425 (8)	−0.0048 (7)	0.0052 (7)	0.0024 (7)
C4	0.0429 (8)	0.0342 (8)	0.0395 (8)	0.0005 (6)	0.0107 (6)	0.0052 (6)
C5	0.0440 (8)	0.0382 (8)	0.0367 (8)	−0.0009 (6)	0.0070 (6)	0.0029 (6)
C6	0.0524 (9)	0.0531 (11)	0.0462 (9)	0.0048 (8)	0.0149 (7)	−0.0062 (8)
C7	0.0420 (9)	0.0655 (13)	0.0641 (11)	0.0074 (8)	0.0137 (8)	−0.0021 (9)
C8	0.0421 (9)	0.0594 (12)	0.0592 (11)	−0.0060 (8)	0.0018 (7)	0.0027 (9)
C9	0.1094 (18)	0.0485 (11)	0.0476 (10)	−0.0042 (11)	0.0247 (11)	0.0001 (8)
C10	0.0690 (12)	0.0457 (10)	0.0487 (10)	−0.0082 (9)	0.0007 (8)	−0.0047 (8)
O1'	0.0515 (7)	0.0706 (9)	0.0478 (7)	−0.0120 (6)	−0.0001 (5)	0.0058 (6)
O2'	0.0581 (8)	0.0701 (10)	0.0703 (9)	−0.0205 (7)	0.0115 (7)	0.0027 (7)
N1'	0.0555 (9)	0.0455 (9)	0.0569 (9)	0.0002 (7)	0.0140 (7)	0.0066 (7)
C1'	0.0571 (11)	0.0656 (13)	0.0535 (10)	0.0049 (9)	0.0038 (8)	0.0141 (9)
C2'	0.0529 (10)	0.0394 (10)	0.0649 (11)	−0.0051 (8)	0.0106 (8)	−0.0029 (8)
C3'	0.0427 (8)	0.0380 (9)	0.0500 (9)	0.0045 (7)	0.0067 (7)	−0.0041 (7)
C4'	0.0410 (8)	0.0437 (9)	0.0435 (8)	0.0047 (7)	0.0065 (6)	0.0002 (7)
C5'	0.0431 (8)	0.0435 (9)	0.0552 (9)	0.0022 (7)	0.0129 (7)	0.0000 (8)
C6'	0.0588 (10)	0.0534 (11)	0.0543 (10)	0.0077 (8)	0.0162 (8)	0.0108 (8)
C7'	0.0679 (12)	0.0727 (14)	0.0452 (10)	0.0100 (10)	0.0034 (8)	0.0042 (9)
C8'	0.0542 (10)	0.0595 (12)	0.0539 (10)	−0.0021 (9)	−0.0019 (8)	−0.0070 (9)
C9'	0.0687 (12)	0.0534 (11)	0.0647 (12)	−0.0026 (10)	0.0224 (9)	−0.0002 (9)
C10'	0.0768 (14)	0.0602 (14)	0.0950 (17)	−0.0200 (11)	0.0375 (13)	−0.0054 (12)

Geometric parameters (Å, º) top

O1—C1	1.456 (2)	O1'—C1'	1.451 (2)
O1—C4	1.3695 (19)	O1'—C4'	1.366 (2)
O2—C5	1.362 (2)	O2'—C5'	1.367 (2)
O2—C10	1.426 (2)	O2'—C10'	1.427 (2)
N1—C1	1.421 (3)	N1'—C1'	1.425 (2)
N1—C2	1.464 (2)	N1'—C2'	1.462 (2)
N1—C9	1.463 (2)	N1'—C9'	1.461 (2)
C1—H1A	0.9700	C1'—H1'A	0.9700
C1—H1B	0.9700	C1'—H1'B	0.9700
C2—H2A	0.9700	C2'—H2'A	0.9700
C2—H2B	0.9700	C2'—H2'B	0.9700
C2—C3	1.512 (2)	C2'—C3'	1.508 (2)
C3—C4	1.389 (2)	C3'—C4'	1.386 (2)
C3—C8	1.391 (2)	C3'—C8'	1.388 (3)
C4—C5	1.404 (2)	C4'—C5'	1.404 (2)
C5—C6	1.382 (2)	C5'—C6'	1.379 (3)
C6—H6	0.9300	C6'—H6'	0.9300
C6—C7	1.389 (3)	C6'—C7'	1.387 (3)
C7—H7	0.9300	C7'—H7'	0.9300
C7—C8	1.370 (3)	C7'—C8'	1.375 (3)
C8—H8	0.9300	C8'—H8'	0.9300
C9—H9A	0.9600	C9'—H9'A	0.9600
C9—H9B	0.9600	C9'—H9'B	0.9600
C9—H9C	0.9600	C9'—H9'C	0.9600
C10—H10D	0.9600	C10'—H10A	0.9600
C10—H10E	0.9600	C10'—H10B	0.9600
C10—H10F	0.9600	C10'—H10C	0.9600

C4—O1—C1	114.28 (13)	C4'—O1'—C1'	113.24 (14)
C5—O2—C10	117.51 (14)	C5'—O2'—C10'	117.90 (17)
C1—N1—C2	108.85 (14)	C1'—N1'—C2'	108.58 (15)
C1—N1—C9	112.13 (16)	C1'—N1'—C9'	112.47 (16)
C9—N1—C2	112.88 (17)	C9'—N1'—C2'	112.64 (15)
O1—C1—H1A	108.6	O1'—C1'—H1'A	108.8
O1—C1—H1B	108.6	O1'—C1'—H1'B	108.8
N1—C1—O1	114.52 (14)	N1'—C1'—O1'	113.74 (15)
N1—C1—H1A	108.6	N1'—C1'—H1'A	108.8
N1—C1—H1B	108.6	N1'—C1'—H1'B	108.8
H1A—C1—H1B	107.6	H1'A—C1'—H1'B	107.7
N1—C2—H2A	109.3	N1'—C2'—H2'A	109.0
N1—C2—H2B	109.3	N1'—C2'—H2'B	109.0
N1—C2—C3	111.61 (15)	N1'—C2'—C3'	112.71 (14)
H2A—C2—H2B	108.0	H2'A—C2'—H2'B	107.8
C3—C2—H2A	109.3	C3'—C2'—H2'A	109.0
C3—C2—H2B	109.3	C3'—C2'—H2'B	109.0
C4—C3—C2	118.41 (16)	C4'—C3'—C2'	119.09 (15)
C4—C3—C8	119.13 (16)	C4'—C3'—C8'	118.99 (17)
C8—C3—C2	122.45 (16)	C8'—C3'—C2'	121.92 (16)
O1—C4—C3	123.36 (15)	O1'—C4'—C3'	122.78 (16)
O1—C4—C5	116.23 (14)	O1'—C4'—C5'	116.67 (15)
C3—C4—C5	120.36 (15)	C3'—C4'—C5'	120.54 (16)
O2—C5—C4	115.17 (14)	O2'—C5'—C4'	114.85 (16)
O2—C5—C6	125.41 (15)	O2'—C5'—C6'	125.68 (17)
C6—C5—C4	119.42 (15)	C6'—C5'—C4'	119.48 (17)
C5—C6—H6	120.0	C5'—C6'—H6'	120.1
C5—C6—C7	119.92 (16)	C5'—C6'—C7'	119.81 (18)
C7—C6—H6	120.0	C7'—C6'—H6'	120.1
C6—C7—H7	119.7	C6'—C7'—H7'	119.7
C8—C7—C6	120.57 (17)	C8'—C7'—C6'	120.59 (18)
C8—C7—H7	119.7	C8'—C7'—H7'	119.7
C3—C8—H8	119.7	C3'—C8'—H8'	119.7
C7—C8—C3	120.59 (16)	C7'—C8'—C3'	120.55 (18)
C7—C8—H8	119.7	C7'—C8'—H8'	119.7
N1—C9—H9A	109.5	N1'—C9'—H9'A	109.5
N1—C9—H9B	109.5	N1'—C9'—H9'B	109.5
N1—C9—H9C	109.5	N1'—C9'—H9'C	109.5
H9A—C9—H9B	109.5	H9'A—C9'—H9'B	109.5
H9A—C9—H9C	109.5	H9'A—C9'—H9'C	109.5
H9B—C9—H9C	109.5	H9'B—C9'—H9'C	109.5
O2—C10—H10D	109.5	O2'—C10'—H10A	109.5
O2—C10—H10E	109.5	O2'—C10'—H10B	109.5
O2—C10—H10F	109.5	O2'—C10'—H10C	109.5
H10D—C10—H10E	109.5	H10A—C10'—H10B	109.5
H10D—C10—H10F	109.5	H10A—C10'—H10C	109.5
H10E—C10—H10F	109.5	H10B—C10'—H10C	109.5

O1—C4—C5—O2	−1.7 (2)	O1'—C4'—C5'—O2'	0.8 (2)
O1—C4—C5—C6	177.98 (15)	O1'—C4'—C5'—C6'	−179.01 (16)
O2—C5—C6—C7	179.74 (17)	O2'—C5'—C6'—C7'	179.68 (18)
N1—C2—C3—C4	−21.6 (2)	N1'—C2'—C3'—C4'	−15.2 (2)
N1—C2—C3—C8	156.76 (17)	N1'—C2'—C3'—C8'	164.96 (17)
C1—O1—C4—C3	−9.1 (2)	C1'—O1'—C4'—C3'	−14.7 (2)
C1—O1—C4—C5	173.47 (14)	C1'—O1'—C4'—C5'	166.48 (16)
C1—N1—C2—C3	50.6 (2)	C1'—N1'—C2'—C3'	45.4 (2)
C2—N1—C1—O1	−62.57 (19)	C2'—N1'—C1'—O1'	−64.2 (2)
C2—C3—C4—O1	0.5 (2)	C2'—C3'—C4'—O1'	−0.7 (2)
C2—C3—C4—C5	177.80 (15)	C2'—C3'—C4'—C5'	178.01 (16)
C2—C3—C8—C7	−178.06 (18)	C2'—C3'—C8'—C7'	−179.74 (18)
C3—C4—C5—O2	−179.24 (14)	C3'—C4'—C5'—O2'	−177.96 (15)
C3—C4—C5—C6	0.5 (2)	C3'—C4'—C5'—C6'	2.2 (3)
C4—O1—C1—N1	41.2 (2)	C4'—O1'—C1'—N1'	48.5 (2)
C4—C3—C8—C7	0.3 (3)	C4'—C3'—C8'—C7'	0.4 (3)
C4—C5—C6—C7	0.1 (3)	C4'—C5'—C6'—C7'	−0.5 (3)
C5—C6—C7—C8	−0.4 (3)	C5'—C6'—C7'—C8'	−1.2 (3)
C6—C7—C8—C3	0.2 (3)	C6'—C7'—C8'—C3'	1.3 (3)
C8—C3—C4—O1	−178.00 (15)	C8'—C3'—C4'—O1'	179.13 (16)
C8—C3—C4—C5	−0.7 (2)	C8'—C3'—C4'—C5'	−2.1 (3)
C9—N1—C1—O1	63.0 (2)	C9'—N1'—C1'—O1'	61.2 (2)
C9—N1—C2—C3	−74.6 (2)	C9'—N1'—C2'—C3'	−79.85 (19)
C10—O2—C5—C4	173.49 (14)	C10'—O2'—C5'—C4'	178.22 (17)
C10—O2—C5—C6	−6.2 (2)	C10'—O2'—C5'—C6'	−1.9 (3)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₂
M_r	179.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	23.4234 (14), 5.0054 (3), 15.9408 (10)
β (°)	97.210 (6)
V (Å³)	1854.2 (2)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.783, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6857, 3281, 2471
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.02
No. of reflections	3281
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the Science and Technology Department of Henan Province of the People's Republic of China (grant No. 122102210111) and the Doctoral Scientific Fund Project of Henan University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gu, Y., Xie, M. L., Liu, X. H., Li, Y., Zhang, J. H., Ling, H., Huang, Y. & Hu, Z. (1998). Chem. Ind. Eng. Prog. pp. 43–47. Google Scholar
Holly, F. W. & Cope, A. C. (1944). J. Am. Chem. Soc. 66, 1875–1879. CrossRef CAS Google Scholar
Ning, X. & Ishida, H. (1994). J. Polym. Sci. Part A Polym. Chem. 32, 1121–1129. CrossRef CAS Web of Science Google Scholar
Rimdusit, S. & Ishida, H. (2000). Polymer, 41, 7941–7949. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stewart, R. (2009). Reinforced Plastics, 53, 28–33. CrossRef Google Scholar
Zheng, L., Zhang, C., Wang, Z., Zhao, P., Liu, X. & Gu, Y. (2011). J. Aero. Mater. 31, 62–66. CAS Google Scholar