7-Chloro-4-phenethyl-2H-1,4-benzoxazin-3(4H)-one

Chen, M.-J.; Yang, H.; Dong, W.-L.; Zuo, H.; Zhou, J.-Z.

doi:10.1107/S1600536809007739

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o712

doi:10.1107/S1600536809007739

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7-Chloro-4-phenethyl-2H-1,4-benzoxazin-3(4H)-one

Ming-Jun Chen,^a Hao Yang,^b Wen-Liang Dong,^c Hua Zuo ^d ^* and Jia-Zhou Zhou ^d

^aCollege of Chemical and Environmental Engineering, Chongqing Three Gorges University, Chongqing 404000, People's Republic of China, ^bCollege of Horticulture and Landscape Architecture, Southwest University, Chongqing 400715, People's Republic of China, ^cSchool of Pharmaceutical Sciences, Shandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China, and ^dCollege of Pharmaceutical Sciences, Southwest University, Chongqing 400716, People's Republic of China
^*Correspondence e-mail: zuohuabest@yahoo.com

(Received 26 February 2009; accepted 3 March 2009; online 6 March 2009)

In the crystal structure of title compound, C₁₆H₁₄ClNO₂, the dihedral angle between the aromatic rings is 4.2 (2)°.

Related literature

For related structures, see: Li et al. (2008 ); Zuo et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₄ClNO₂
M_r = 287.73
Orthorhombic, I b a 2
a = 13.528 (4) Å
b = 29.616 (10) Å
c = 7.074 (2) Å
V = 2834.2 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.968, T_max = 0.984
7036 measured reflections
2171 independent reflections
1343 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.117
S = 1.00
2171 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 797 Friedel pairs
Flack parameter: 0.04 (13)

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007739/nc2136sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007739/nc2136Isup2.hkl

checkCIF report

Comment top

As part of our continuing project on the study of the interactions occurring between small molecules and proteins (Li et al., 2008; Zuo et al., 2008), we report here the synthesis and crystal structure of the title compound. In the crystal structure, the two ring systems are nearly coplanar, the diehderal angle between the aromatic rings being 4.2 (2)°.

Related literature top

For related structures, see: Li et al. (2008); Zuo et al. (2008).

Experimental top

To the solution of 2-(2,4-dichlorophenoxy)-N-phenethylacetamide (0.684 g, 2.0 mmol) in DMF (20 ml), caesium carbonate (0.787 g, 2.4 mmol) was added. The mixture was refluxed for 1.5 h. After completion of the reaction (by TLC monitoring), the DMF was removed under vacuum. Water (20 ml) was added into the residue to obtain a turbid solution and it was extracted by ethyl acetate (20 ml x 4). The combined organic layers were washed three times with 10 mL of 1 mol/L hydrochloric acid and saturated sodium chloride solution (10 ml x 3), dried over MgSO₄. And then the mixture was filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl/acetate = 1/5 as eluent (yield 75%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solutionof the solid dissolved in ethyl acetate/hexane at room temperature for 10 days.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.

7-Chloro-4-phenethyl-2H-1,4-benzoxazin-3(4H)-one top

Crystal data top

C₁₆H₁₄ClNO₂	F(000) = 1200
M_r = 287.73	D_x = 1.349 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 809 reflections
a = 13.528 (4) Å	θ = 2.6–18.3°
b = 29.616 (10) Å	µ = 0.27 mm⁻¹
c = 7.074 (2) Å	T = 298 K
V = 2834.2 (15) Å³	Block, colorless
Z = 8	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	1343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→16
T_min = 0.968, T_max = 0.984	k = −34→34
7036 measured reflections	l = −8→7

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.04P)² + 1.1309P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.15 e Å⁻³
2171 reflections	Δρ_min = −0.16 e Å⁻³
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0057 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 797 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.04 (13)

Crystal data top

C₁₆H₁₄ClNO₂	V = 2834.2 (15) Å³
M_r = 287.73	Z = 8
Orthorhombic, Iba2	Mo Kα radiation
a = 13.528 (4) Å	µ = 0.27 mm⁻¹
b = 29.616 (10) Å	T = 298 K
c = 7.074 (2) Å	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2171 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1343 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.984	R_int = 0.067
7036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.117	Δρ_max = 0.15 e Å⁻³
S = 1.00	Δρ_min = −0.16 e Å⁻³
2171 reflections	Absolute structure: Flack (1983), 797 Friedel pairs
182 parameters	Absolute structure parameter: 0.04 (13)
0 restraints

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.The absolute structure was determined on the basis of 800 Friedel pairs.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.42978 (9)	0.23193 (3)	−0.4987 (3)	0.1035 (6)
O1	0.4487 (2)	0.39965 (8)	−0.4216 (4)	0.0762 (10)
O2	0.3501 (2)	0.47560 (9)	−0.0754 (4)	0.0776 (10)
N1	0.3137 (2)	0.40207 (11)	−0.1198 (5)	0.0524 (9)
C1	0.3939 (3)	0.28154 (13)	−0.3869 (7)	0.0641 (12)
C2	0.3273 (4)	0.28028 (16)	−0.2421 (9)	0.0824 (15)
H2	0.3002	0.2530	−0.2033	0.099*
C3	0.3007 (3)	0.32009 (15)	−0.1536 (7)	0.0754 (13)
H3	0.2548	0.3193	−0.0557	0.091*
C4	0.3405 (3)	0.36100 (13)	−0.2074 (6)	0.0489 (10)
C5	0.4080 (3)	0.36097 (13)	−0.3538 (6)	0.0520 (10)
C6	0.4356 (3)	0.32152 (12)	−0.4442 (6)	0.0586 (11)
H6	0.4815	0.3221	−0.5420	0.070*
C7	0.4403 (3)	0.43887 (13)	−0.3107 (7)	0.0608 (11)
H7A	0.4279	0.4640	−0.3956	0.073*
H7B	0.5041	0.4442	−0.2523	0.073*
C8	0.3644 (3)	0.44065 (14)	−0.1590 (6)	0.0556 (11)
C9	0.2368 (3)	0.40386 (14)	0.0274 (6)	0.0640 (11)
H9A	0.1854	0.3822	−0.0027	0.077*
H9B	0.2071	0.4337	0.0278	0.077*
C10	0.2775 (3)	0.39363 (18)	0.2246 (7)	0.0811 (14)
H10A	0.3003	0.3626	0.2285	0.097*
H10B	0.3338	0.4130	0.2491	0.097*
C11	0.2016 (3)	0.40062 (16)	0.3760 (6)	0.0581 (11)
C12	0.1471 (3)	0.36580 (15)	0.4534 (7)	0.0721 (12)
H12	0.1573	0.3364	0.4120	0.087*
C13	0.0770 (3)	0.37441 (18)	0.5926 (8)	0.0776 (14)
H13	0.0415	0.3507	0.6453	0.093*
C14	0.0605 (3)	0.4166 (2)	0.6510 (7)	0.0797 (14)
H14	0.0122	0.4219	0.7419	0.096*
C15	0.1123 (4)	0.45149 (17)	0.5808 (7)	0.0819 (14)
H15	0.1010	0.4807	0.6240	0.098*
C16	0.1827 (3)	0.44326 (15)	0.4432 (7)	0.0724 (12)
H16	0.2185	0.4674	0.3946	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0963 (9)	0.0644 (7)	0.1497 (14)	−0.0060 (7)	0.0085 (10)	−0.0330 (9)
O1	0.110 (2)	0.0537 (15)	0.064 (2)	−0.0103 (15)	0.038 (2)	−0.0038 (16)
O2	0.088 (2)	0.0731 (19)	0.072 (3)	0.0146 (16)	0.0006 (19)	−0.0206 (18)
N1	0.048 (2)	0.071 (2)	0.038 (2)	0.0065 (17)	0.0033 (17)	−0.0021 (18)
C1	0.058 (2)	0.057 (2)	0.078 (3)	−0.002 (2)	−0.004 (3)	−0.009 (2)
C2	0.079 (3)	0.061 (3)	0.108 (4)	−0.015 (2)	0.015 (3)	0.005 (3)
C3	0.064 (3)	0.079 (3)	0.083 (3)	−0.010 (2)	0.022 (2)	0.005 (3)
C4	0.044 (2)	0.057 (2)	0.046 (2)	0.0034 (19)	0.000 (2)	0.005 (2)
C5	0.050 (2)	0.055 (2)	0.051 (3)	−0.0021 (19)	0.002 (2)	0.007 (2)
C6	0.054 (2)	0.060 (2)	0.062 (3)	0.000 (2)	0.009 (2)	−0.001 (2)
C7	0.064 (2)	0.058 (2)	0.061 (3)	0.006 (2)	0.003 (2)	−0.001 (2)
C8	0.054 (3)	0.064 (3)	0.049 (3)	0.011 (2)	−0.005 (2)	−0.006 (2)
C9	0.051 (2)	0.094 (3)	0.047 (3)	0.016 (2)	0.002 (2)	−0.004 (2)
C10	0.059 (2)	0.132 (4)	0.052 (3)	0.015 (3)	0.002 (2)	0.009 (3)
C11	0.048 (2)	0.087 (3)	0.039 (3)	0.006 (2)	−0.003 (2)	0.007 (2)
C12	0.083 (3)	0.074 (3)	0.059 (3)	0.000 (3)	−0.010 (3)	0.002 (3)
C13	0.071 (3)	0.097 (3)	0.065 (3)	−0.023 (3)	0.000 (3)	0.021 (3)
C14	0.063 (3)	0.127 (4)	0.049 (3)	0.001 (3)	0.006 (2)	0.000 (3)
C15	0.089 (3)	0.088 (3)	0.069 (3)	0.007 (3)	−0.001 (3)	−0.023 (3)
C16	0.070 (3)	0.082 (3)	0.066 (3)	−0.021 (2)	0.003 (3)	0.000 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.737 (4)	C7—H7B	0.9700
O1—C5	1.359 (4)	C9—C10	1.529 (6)
O1—C7	1.406 (4)	C9—H9A	0.9700
O2—C8	1.208 (4)	C9—H9B	0.9700
N1—C8	1.361 (5)	C10—C11	1.498 (6)
N1—C4	1.413 (5)	C10—H10A	0.9700
N1—C9	1.473 (5)	C10—H10B	0.9700
C1—C2	1.365 (7)	C11—C16	1.373 (5)
C1—C6	1.372 (5)	C11—C12	1.381 (6)
C2—C3	1.383 (6)	C12—C13	1.390 (6)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.380 (5)	C13—C14	1.335 (6)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.381 (5)	C14—C15	1.344 (6)
C5—C6	1.383 (5)	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.383 (6)
C7—C8	1.486 (5)	C15—H15	0.9300
C7—H7A	0.9700	C16—H16	0.9300

C5—O1—C7	117.8 (3)	N1—C9—C10	112.6 (3)
C8—N1—C4	120.2 (3)	N1—C9—H9A	109.1
C8—N1—C9	118.0 (3)	C10—C9—H9A	109.1
C4—N1—C9	121.5 (3)	N1—C9—H9B	109.1
C2—C1—C6	121.1 (4)	C10—C9—H9B	109.1
C2—C1—Cl1	120.2 (4)	H9A—C9—H9B	107.8
C6—C1—Cl1	118.7 (4)	C11—C10—C9	112.2 (3)
C1—C2—C3	119.3 (4)	C11—C10—H10A	109.2
C1—C2—H2	120.4	C9—C10—H10A	109.2
C3—C2—H2	120.4	C11—C10—H10B	109.2
C4—C3—C2	121.5 (4)	C9—C10—H10B	109.2
C4—C3—H3	119.3	H10A—C10—H10B	107.9
C2—C3—H3	119.3	C16—C11—C12	116.7 (4)
C3—C4—C5	117.7 (4)	C16—C11—C10	120.1 (4)
C3—C4—N1	122.3 (4)	C12—C11—C10	123.1 (5)
C5—C4—N1	120.0 (3)	C11—C12—C13	120.5 (4)
O1—C5—C4	122.1 (4)	C11—C12—H12	119.7
O1—C5—C6	116.1 (4)	C13—C12—H12	119.7
C4—C5—C6	121.7 (4)	C14—C13—C12	120.4 (4)
C1—C6—C5	118.8 (4)	C14—C13—H13	119.8
C1—C6—H6	120.6	C12—C13—H13	119.8
C5—C6—H6	120.6	C13—C14—C15	121.2 (5)
O1—C7—C8	119.2 (3)	C13—C14—H14	119.4
O1—C7—H7A	107.5	C15—C14—H14	119.4
C8—C7—H7A	107.5	C14—C15—C16	118.9 (5)
O1—C7—H7B	107.5	C14—C15—H15	120.5
C8—C7—H7B	107.5	C16—C15—H15	120.5
H7A—C7—H7B	107.0	C11—C16—C15	122.3 (4)
O2—C8—N1	122.6 (4)	C11—C16—H16	118.9
O2—C8—C7	119.7 (4)	C15—C16—H16	118.9
N1—C8—C7	117.8 (4)

C6—C1—C2—C3	0.8 (7)	C4—N1—C8—O2	−173.2 (4)
Cl1—C1—C2—C3	179.2 (4)	C9—N1—C8—O2	1.6 (6)
C1—C2—C3—C4	−0.6 (8)	C4—N1—C8—C7	6.6 (5)
C2—C3—C4—C5	0.3 (7)	C9—N1—C8—C7	−178.6 (3)
C2—C3—C4—N1	179.5 (4)	O1—C7—C8—O2	−172.8 (4)
C8—N1—C4—C3	171.0 (4)	O1—C7—C8—N1	7.4 (6)
C9—N1—C4—C3	−3.6 (6)	C8—N1—C9—C10	−89.3 (5)
C8—N1—C4—C5	−9.8 (5)	C4—N1—C9—C10	85.4 (5)
C9—N1—C4—C5	175.6 (3)	N1—C9—C10—C11	173.5 (4)
C7—O1—C5—C4	15.7 (5)	C9—C10—C11—C16	−81.2 (6)
C7—O1—C5—C6	−166.4 (4)	C9—C10—C11—C12	98.2 (5)
C3—C4—C5—O1	177.5 (4)	C16—C11—C12—C13	−0.1 (6)
N1—C4—C5—O1	−1.7 (5)	C10—C11—C12—C13	−179.5 (4)
C3—C4—C5—C6	−0.2 (6)	C11—C12—C13—C14	1.1 (7)
N1—C4—C5—C6	−179.5 (4)	C12—C13—C14—C15	−1.6 (8)
C2—C1—C6—C5	−0.8 (7)	C13—C14—C15—C16	1.1 (8)
Cl1—C1—C6—C5	−179.2 (3)	C12—C11—C16—C15	−0.4 (7)
O1—C5—C6—C1	−177.4 (4)	C10—C11—C16—C15	179.0 (4)
C4—C5—C6—C1	0.5 (6)	C14—C15—C16—C11	−0.1 (7)
C5—O1—C7—C8	−18.3 (5)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClNO₂
M_r	287.73
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	298
a, b, c (Å)	13.528 (4), 29.616 (10), 7.074 (2)
V (Å³)	2834.2 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.968, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7036, 2171, 1343
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.117, 1.00
No. of reflections	2171
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Absolute structure	Flack (1983), 797 Friedel pairs
Absolute structure parameter	0.04 (13)

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Acknowledgements

This study was supported by the Research Fund for the Doctoral Program of Southwest University, China (grant No. SWUB2008027).

References

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