organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 ππ inter­actions are observed in the crystal structure.

Related literature

For the synthesis and applications of 1,3-benzoxazines, see: Holly & Cope (1944[Holly, F. W. & Cope, A. C. (1944). J. Am. Chem. Soc. 66, 1875-1879.]); Gu et al. (1998[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.]); Zheng et al. (2011[Zheng, L., Zhang, C., Wang, Z., Zhao, P., Liu, X. & Gu, Y. (2011). J. Aero. Mater. 31, 62-66.]); Rimdusit & Ishida (2000[Rimdusit, S. & Ishida, H. (2000). Polymer, 41, 7941-7949.]); Stewart (2009[Stewart, R. (2009). Reinforced Plastics, 53, 28-33.]); Ning & Ishida (1994[Ning, X. & Ishida, H. (1994). J. Polym. Sci. Part A Polym. Chem. 32, 1121-1129.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NO2

  • Mr = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.783, Tmax = 1.000

  • 6857 measured reflections

  • 3281 independent reflections

  • 2471 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.02

  • 3281 reflections

  • 240 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


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 ππ 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.

Refinement top

All H atoms were refined using a riding model approximation, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

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
[Figure 1] 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
C10H13NO2F(000) = 768
Mr = 179.21Dx = 1.284 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 2369 reflections
a = 23.4234 (14) Åθ = 3.2–66.9°
b = 5.0054 (3) ŵ = 0.73 mm1
c = 15.9408 (10) ÅT = 291 K
β = 97.210 (6)°Prism, colourless
V = 1854.2 (2) Å30.22 × 0.20 × 0.18 mm
Z = 8
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
3281 independent reflections
Radiation source: Enhance (Cu) X-ray Source2471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 16.2312 pixels mm-1θmax = 67.1°, θmin = 3.8°
ω scansh = 1927
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 35
Tmin = 0.783, Tmax = 1.000l = 1819
6857 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0524P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3281 reflectionsΔρmax = 0.15 e Å3
240 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0041 (3)
Crystal data top
C10H13NO2V = 1854.2 (2) Å3
Mr = 179.21Z = 8
Monoclinic, P21/cCu Kα radiation
a = 23.4234 (14) ŵ = 0.73 mm1
b = 5.0054 (3) ÅT = 291 K
c = 15.9408 (10) Å0.22 × 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)
Tmin = 0.783, Tmax = 1.000Rint = 0.030
6857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.02Δρmax = 0.15 e Å3
3281 reflectionsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O10.93754 (5)0.7027 (2)0.81029 (8)0.0481 (3)
O20.93639 (5)1.0466 (3)0.93130 (8)0.0507 (3)
N10.89328 (8)0.5131 (3)0.67831 (9)0.0538 (4)
C10.93598 (8)0.4853 (3)0.74936 (12)0.0526 (4)
H1A0.97340.47250.72940.063*
H1B0.92930.31920.77790.063*
C20.83649 (9)0.5122 (4)0.70753 (12)0.0549 (5)
H2A0.82820.33430.72680.066*
H2B0.80750.55740.66070.066*
C30.83340 (7)0.7092 (3)0.77871 (10)0.0429 (4)
C40.88444 (7)0.7904 (3)0.82559 (10)0.0384 (3)
C50.88378 (7)0.9799 (3)0.89037 (9)0.0395 (3)
C60.83181 (8)1.0838 (4)0.90755 (11)0.0498 (4)
H60.83091.20960.95030.060*
C70.78089 (8)1.0000 (4)0.86090 (12)0.0566 (5)
H70.74601.06940.87290.068*
C80.78165 (8)0.8159 (4)0.79739 (12)0.0540 (5)
H80.74720.76200.76650.065*
C90.90299 (11)0.7484 (4)0.62759 (12)0.0672 (6)
H9A0.89770.90700.65950.101*
H9B0.87610.74810.57690.101*
H9C0.94150.74450.61310.101*
C100.93882 (9)1.2585 (4)0.99146 (12)0.0551 (5)
H10D0.97781.28231.01700.083*
H10E0.91501.21531.03430.083*
H10F0.92531.42060.96350.083*
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'A0.34300.74440.22730.071*
H1'B0.33830.91840.30780.071*
C2'0.43450 (8)0.8338 (4)0.39037 (12)0.0521 (4)
H2'A0.42571.01710.40370.063*
H2'B0.47590.81070.40200.063*
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)
H6'0.33340.18060.58060.066*
C7'0.39836 (9)0.4464 (4)0.58138 (12)0.0622 (5)
H7'0.41180.42990.63860.075*
C8'0.42559 (8)0.6174 (4)0.53176 (12)0.0566 (5)
H8'0.45770.71290.55550.068*
C9'0.44587 (9)0.5579 (4)0.26797 (13)0.0611 (5)
H9'A0.43350.53810.20860.092*
H9'B0.43670.39860.29710.092*
H9'C0.48670.58700.27690.092*
C10'0.25623 (10)0.0001 (5)0.46693 (16)0.0750 (7)
H10A0.22760.09190.42920.113*
H10B0.23810.08920.50990.113*
H10C0.28390.12620.49290.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0447 (6)0.0478 (7)0.0533 (7)0.0041 (5)0.0126 (5)0.0065 (5)
O20.0476 (6)0.0544 (8)0.0491 (7)0.0022 (5)0.0019 (5)0.0106 (5)
N10.0802 (11)0.0369 (8)0.0467 (8)0.0029 (7)0.0177 (7)0.0041 (6)
C10.0652 (11)0.0365 (9)0.0600 (11)0.0048 (8)0.0233 (9)0.0010 (8)
C20.0696 (11)0.0432 (10)0.0512 (10)0.0098 (9)0.0047 (8)0.0056 (8)
C30.0495 (9)0.0367 (9)0.0425 (8)0.0048 (7)0.0052 (7)0.0024 (7)
C40.0429 (8)0.0342 (8)0.0395 (8)0.0005 (6)0.0107 (6)0.0052 (6)
C50.0440 (8)0.0382 (8)0.0367 (8)0.0009 (6)0.0070 (6)0.0029 (6)
C60.0524 (9)0.0531 (11)0.0462 (9)0.0048 (8)0.0149 (7)0.0062 (8)
C70.0420 (9)0.0655 (13)0.0641 (11)0.0074 (8)0.0137 (8)0.0021 (9)
C80.0421 (9)0.0594 (12)0.0592 (11)0.0060 (8)0.0018 (7)0.0027 (9)
C90.1094 (18)0.0485 (11)0.0476 (10)0.0042 (11)0.0247 (11)0.0001 (8)
C100.0690 (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—C11.456 (2)O1'—C1'1.451 (2)
O1—C41.3695 (19)O1'—C4'1.366 (2)
O2—C51.362 (2)O2'—C5'1.367 (2)
O2—C101.426 (2)O2'—C10'1.427 (2)
N1—C11.421 (3)N1'—C1'1.425 (2)
N1—C21.464 (2)N1'—C2'1.462 (2)
N1—C91.463 (2)N1'—C9'1.461 (2)
C1—H1A0.9700C1'—H1'A0.9700
C1—H1B0.9700C1'—H1'B0.9700
C2—H2A0.9700C2'—H2'A0.9700
C2—H2B0.9700C2'—H2'B0.9700
C2—C31.512 (2)C2'—C3'1.508 (2)
C3—C41.389 (2)C3'—C4'1.386 (2)
C3—C81.391 (2)C3'—C8'1.388 (3)
C4—C51.404 (2)C4'—C5'1.404 (2)
C5—C61.382 (2)C5'—C6'1.379 (3)
C6—H60.9300C6'—H6'0.9300
C6—C71.389 (3)C6'—C7'1.387 (3)
C7—H70.9300C7'—H7'0.9300
C7—C81.370 (3)C7'—C8'1.375 (3)
C8—H80.9300C8'—H8'0.9300
C9—H9A0.9600C9'—H9'A0.9600
C9—H9B0.9600C9'—H9'B0.9600
C9—H9C0.9600C9'—H9'C0.9600
C10—H10D0.9600C10'—H10A0.9600
C10—H10E0.9600C10'—H10B0.9600
C10—H10F0.9600C10'—H10C0.9600
C4—O1—C1114.28 (13)C4'—O1'—C1'113.24 (14)
C5—O2—C10117.51 (14)C5'—O2'—C10'117.90 (17)
C1—N1—C2108.85 (14)C1'—N1'—C2'108.58 (15)
C1—N1—C9112.13 (16)C1'—N1'—C9'112.47 (16)
C9—N1—C2112.88 (17)C9'—N1'—C2'112.64 (15)
O1—C1—H1A108.6O1'—C1'—H1'A108.8
O1—C1—H1B108.6O1'—C1'—H1'B108.8
N1—C1—O1114.52 (14)N1'—C1'—O1'113.74 (15)
N1—C1—H1A108.6N1'—C1'—H1'A108.8
N1—C1—H1B108.6N1'—C1'—H1'B108.8
H1A—C1—H1B107.6H1'A—C1'—H1'B107.7
N1—C2—H2A109.3N1'—C2'—H2'A109.0
N1—C2—H2B109.3N1'—C2'—H2'B109.0
N1—C2—C3111.61 (15)N1'—C2'—C3'112.71 (14)
H2A—C2—H2B108.0H2'A—C2'—H2'B107.8
C3—C2—H2A109.3C3'—C2'—H2'A109.0
C3—C2—H2B109.3C3'—C2'—H2'B109.0
C4—C3—C2118.41 (16)C4'—C3'—C2'119.09 (15)
C4—C3—C8119.13 (16)C4'—C3'—C8'118.99 (17)
C8—C3—C2122.45 (16)C8'—C3'—C2'121.92 (16)
O1—C4—C3123.36 (15)O1'—C4'—C3'122.78 (16)
O1—C4—C5116.23 (14)O1'—C4'—C5'116.67 (15)
C3—C4—C5120.36 (15)C3'—C4'—C5'120.54 (16)
O2—C5—C4115.17 (14)O2'—C5'—C4'114.85 (16)
O2—C5—C6125.41 (15)O2'—C5'—C6'125.68 (17)
C6—C5—C4119.42 (15)C6'—C5'—C4'119.48 (17)
C5—C6—H6120.0C5'—C6'—H6'120.1
C5—C6—C7119.92 (16)C5'—C6'—C7'119.81 (18)
C7—C6—H6120.0C7'—C6'—H6'120.1
C6—C7—H7119.7C6'—C7'—H7'119.7
C8—C7—C6120.57 (17)C8'—C7'—C6'120.59 (18)
C8—C7—H7119.7C8'—C7'—H7'119.7
C3—C8—H8119.7C3'—C8'—H8'119.7
C7—C8—C3120.59 (16)C7'—C8'—C3'120.55 (18)
C7—C8—H8119.7C7'—C8'—H8'119.7
N1—C9—H9A109.5N1'—C9'—H9'A109.5
N1—C9—H9B109.5N1'—C9'—H9'B109.5
N1—C9—H9C109.5N1'—C9'—H9'C109.5
H9A—C9—H9B109.5H9'A—C9'—H9'B109.5
H9A—C9—H9C109.5H9'A—C9'—H9'C109.5
H9B—C9—H9C109.5H9'B—C9'—H9'C109.5
O2—C10—H10D109.5O2'—C10'—H10A109.5
O2—C10—H10E109.5O2'—C10'—H10B109.5
O2—C10—H10F109.5O2'—C10'—H10C109.5
H10D—C10—H10E109.5H10A—C10'—H10B109.5
H10D—C10—H10F109.5H10A—C10'—H10C109.5
H10E—C10—H10F109.5H10B—C10'—H10C109.5
O1—C4—C5—O21.7 (2)O1'—C4'—C5'—O2'0.8 (2)
O1—C4—C5—C6177.98 (15)O1'—C4'—C5'—C6'179.01 (16)
O2—C5—C6—C7179.74 (17)O2'—C5'—C6'—C7'179.68 (18)
N1—C2—C3—C421.6 (2)N1'—C2'—C3'—C4'15.2 (2)
N1—C2—C3—C8156.76 (17)N1'—C2'—C3'—C8'164.96 (17)
C1—O1—C4—C39.1 (2)C1'—O1'—C4'—C3'14.7 (2)
C1—O1—C4—C5173.47 (14)C1'—O1'—C4'—C5'166.48 (16)
C1—N1—C2—C350.6 (2)C1'—N1'—C2'—C3'45.4 (2)
C2—N1—C1—O162.57 (19)C2'—N1'—C1'—O1'64.2 (2)
C2—C3—C4—O10.5 (2)C2'—C3'—C4'—O1'0.7 (2)
C2—C3—C4—C5177.80 (15)C2'—C3'—C4'—C5'178.01 (16)
C2—C3—C8—C7178.06 (18)C2'—C3'—C8'—C7'179.74 (18)
C3—C4—C5—O2179.24 (14)C3'—C4'—C5'—O2'177.96 (15)
C3—C4—C5—C60.5 (2)C3'—C4'—C5'—C6'2.2 (3)
C4—O1—C1—N141.2 (2)C4'—O1'—C1'—N1'48.5 (2)
C4—C3—C8—C70.3 (3)C4'—C3'—C8'—C7'0.4 (3)
C4—C5—C6—C70.1 (3)C4'—C5'—C6'—C7'0.5 (3)
C5—C6—C7—C80.4 (3)C5'—C6'—C7'—C8'1.2 (3)
C6—C7—C8—C30.2 (3)C6'—C7'—C8'—C3'1.3 (3)
C8—C3—C4—O1178.00 (15)C8'—C3'—C4'—O1'179.13 (16)
C8—C3—C4—C50.7 (2)C8'—C3'—C4'—C5'2.1 (3)
C9—N1—C1—O163.0 (2)C9'—N1'—C1'—O1'61.2 (2)
C9—N1—C2—C374.6 (2)C9'—N1'—C2'—C3'79.85 (19)
C10—O2—C5—C4173.49 (14)C10'—O2'—C5'—C4'178.22 (17)
C10—O2—C5—C66.2 (2)C10'—O2'—C5'—C6'1.9 (3)

Experimental details

Crystal data
Chemical formulaC10H13NO2
Mr179.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)23.4234 (14), 5.0054 (3), 15.9408 (10)
β (°) 97.210 (6)
V3)1854.2 (2)
Z8
Radiation typeCu Kα
µ (mm1)0.73
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerAgilent Xcalibur (Eos, Gemini)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.783, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6857, 3281, 2471
Rint0.030
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.114, 1.02
No. of reflections3281
No. of parameters240
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

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