Methyl 2-(2-hydroxy­acetamido)benzoate

Alam, S.; Saeed, S.; Fischer, A.; Khan, N.

doi:10.1107/S1600536810009451

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o913

doi:10.1107/S1600536810009451

Open

access

Methyl 2-(2-hydroxyacetamido)benzoate

Samina Alam,^a Sadaf Saeed,^a ^* Andreas Fischer ^b and Naeema Khan ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bInorganic Chemistry, School of Chemical Science and Engineering, Royal Institute of Technology (KTH), 100 44 Stockholm, Sweden
^*Correspondence e-mail: sadaf03_2000@yahoo.com

(Received 19 January 2010; accepted 12 March 2010; online 24 March 2010)

The title compound, C₁₀H₁₁NO₄, was formed from 4,1-benzoxazepine-2,5(1H,3H)-dione and ammonia gas. Intramolecular hydrogen bonding is present between the amide N—H group and the carbonyl O atom of the ester group. The crystal structure features intermolecular O—H⋯O hydrogen bonds.

Related literature

For the pharmagological activity of different quinazolinones, see: Kenichi et al. (1985 ); Lyle (1985a ,b ); Mhaske & Argade (2006 ); Xia et al. (2001 ). For details of the synthesis, see: Iacobelli et al. (1965 ); Uskokovic et al. (1964 ).

Experimental

Crystal data

C₁₀H₁₁NO₄
M_r = 209.20
Orthorhombic, P 2₁ 2₁ 2₁
a = 3.938 (2) Å
b = 8.808 (4) Å
c = 27.94 (4) Å
V = 969.1 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 299 K
0.60 × 0.13 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
7794 measured reflections
1107 independent reflections
846 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.127
S = 1.12
1107 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.90	1.95	2.669 (4)	136
O1—H1⋯O2ⁱ	0.90	1.91	2.758 (4)	157
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DIRAX (Duisenberg, 1992 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009451/om2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009451/om2318Isup2.hkl

checkCIF report

Comment top

4,1-Benzoxazepin-2,5-diones are synthetic heterocyclic compounds that can be converted to quinazolinones which have a broad range of pharmacological activities (Xia et al., 2001; Kenichi et al., 1985; Lyle, 1985a,b; Mhaske & Argade, 2006). The title compound (I) (Fig. 1) was formed in a ring-cleaving reaction of 4,1-benzoxazepin-2,5-dione and gaseous ammonia (Fig. 2), instead of the expected ring contraction product i.e.quinazolinone. The crystal packing of the title compound is stabilized by intermolecular O–H···O bonding. Additionally, intramolecular N–H···O bonds are present.

Related literature top

For the pharmagological activity of different quinazolinones, see: Kenichi et al. (1985); Lyle (1985a,b); Mhaske & Argade (2006); Xia et al. (2001). For synthetic details, see: Iacobelli et al. (1965); Uskokovic et al. (1964).

Experimental top

4,1-benzoxazepin-2,5(1H,3H)-dione was prepared from the corresponding 2-[(2-chloroethanoyl)amino]benzoic acid (Iacobelli et al., 1965). Ammonia gas was passed through the suspension of 4,1-benzoxazepin-2,5(1H,3H)-dione (3 g, 0.0169 mole) in dry methanol (400 ml) for three hours and kept at room temperature for seven days. After workup according to reported procedure (Uskokovic et al., 1964) the residue was collected and recrystallized from methanol to give the title compound (I), m.p. 161 °C, yield 31%, R_f 0.76 acetone / benzene (3:7). The undissolved part was recrystallized from hot water to give 2-(1-hydroxymethyl)-4(3H)-quinazolinone, m.p. 214 °C; yield 16%, R_f 0.35 acetone / benzene (3:7).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Ellipsoid plot.
	Fig. 2. The prepapration of the title compound.

Methyl 2-(2-hydroxyacetamido)benzoate top

Crystal data top

C₁₀H₁₁NO₄	F(000) = 440
M_r = 209.20	D_x = 1.434 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20 reflections
a = 3.938 (2) Å	θ = 5.9–19.1°
b = 8.808 (4) Å	µ = 0.11 mm⁻¹
c = 27.94 (4) Å	T = 299 K
V = 969.1 (15) Å³	Needle, colourless
Z = 4	0.60 × 0.13 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.104
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 4.6°
ϕ and ω scans	h = −4→4
7794 measured reflections	k = −10→10
1107 independent reflections	l = −33→33
846 reflections with I > 2σ(I)

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0491P)² + 0.4762P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
1107 reflections	Δρ_max = 0.18 e Å⁻³
137 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Crystal data top

C₁₀H₁₁NO₄	V = 969.1 (15) Å³
M_r = 209.20	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 3.938 (2) Å	µ = 0.11 mm⁻¹
b = 8.808 (4) Å	T = 299 K
c = 27.94 (4) Å	0.60 × 0.13 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	846 reflections with I > 2σ(I)
7794 measured reflections	R_int = 0.104
1107 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.12	Δρ_max = 0.18 e Å⁻³
1107 reflections	Δρ_min = −0.21 e Å⁻³
137 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	0.9247 (10)	0.4009 (4)	0.09627 (12)	0.0331 (9)
C2	1.0237 (11)	0.3866 (4)	0.04884 (13)	0.0425 (10)
C3	1.1821 (12)	0.5015 (5)	0.02483 (13)	0.0467 (11)
C4	1.2470 (12)	0.6356 (5)	0.04868 (14)	0.0468 (11)
C5	1.1577 (11)	0.6541 (4)	0.09563 (13)	0.0421 (10)
C6	0.9931 (9)	0.5380 (4)	0.12037 (12)	0.0338 (9)
C7	0.9656 (11)	0.6678 (4)	0.19938 (13)	0.0382 (10)
C8	0.8338 (11)	0.6424 (4)	0.24887 (13)	0.0429 (10)
C9	0.7492 (10)	0.2746 (4)	0.12057 (13)	0.0368 (9)
C10	0.5821 (14)	0.0186 (4)	0.11595 (17)	0.0627 (14)
N1	0.8981 (9)	0.5541 (3)	0.16834 (10)	0.0367 (8)
O1	0.6276 (7)	0.5119 (3)	0.25294 (8)	0.0482 (8)
O2	1.1235 (9)	0.7833 (3)	0.18947 (9)	0.0545 (9)
O3	0.6172 (9)	0.2797 (3)	0.15945 (10)	0.0546 (8)
O4	0.7495 (8)	0.1475 (3)	0.09478 (9)	0.0529 (8)
H2	0.9631	0.2943	0.0312	0.051*
H3	1.2568	0.4854	−0.0104	0.056*
H4	1.3879	0.7148	0.0317	0.056*
H5	1.2063	0.7559	0.1121	0.051*
H8A	0.6860	0.7378	0.2595	0.051*
H8B	1.0239	0.6257	0.2695	0.051*
H10A	0.7049	−0.0132	0.1439	0.075*
H10B	0.5749	−0.0631	0.0932	0.075*
H10C	0.3548	0.0462	0.1248	0.075*
H1N	0.7402	0.4862	0.1774	0.044*
H1	0.7463	0.4332	0.2647	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.0260 (18)	0.0351 (17)	0.0004 (18)	−0.0033 (18)	0.0036 (15)
C2	0.050 (3)	0.037 (2)	0.041 (2)	−0.002 (2)	−0.003 (2)	−0.0059 (17)
C3	0.055 (3)	0.049 (2)	0.0360 (18)	0.002 (2)	0.004 (2)	0.002 (2)
C4	0.052 (3)	0.043 (2)	0.045 (2)	−0.005 (2)	0.005 (2)	0.0112 (19)
C5	0.050 (3)	0.032 (2)	0.044 (2)	−0.008 (2)	0.002 (2)	0.0064 (18)
C6	0.033 (2)	0.034 (2)	0.0344 (17)	−0.0008 (18)	−0.0028 (17)	0.0025 (16)
C7	0.042 (2)	0.0298 (19)	0.043 (2)	0.002 (2)	−0.0050 (18)	−0.0055 (17)
C8	0.046 (2)	0.040 (2)	0.0422 (19)	0.005 (2)	−0.001 (2)	−0.0041 (18)
C9	0.039 (2)	0.0304 (19)	0.0405 (19)	−0.0024 (19)	−0.005 (2)	−0.0016 (17)
C10	0.075 (4)	0.030 (2)	0.083 (3)	−0.015 (3)	0.006 (3)	0.001 (2)
N1	0.0444 (19)	0.0288 (15)	0.0370 (15)	−0.0097 (17)	0.0031 (16)	−0.0025 (13)
O1	0.060 (2)	0.0346 (14)	0.0502 (14)	0.0024 (16)	0.0045 (16)	0.0060 (13)
O2	0.079 (2)	0.0317 (14)	0.0528 (15)	−0.0158 (18)	0.0039 (17)	−0.0075 (13)
O3	0.079 (2)	0.0363 (14)	0.0487 (15)	−0.0143 (18)	0.0146 (17)	−0.0024 (13)
O4	0.073 (2)	0.0281 (14)	0.0577 (16)	−0.0129 (15)	0.0110 (17)	−0.0084 (13)

Geometric parameters (Å, º) top

C1—C2	1.387 (5)	C9—O4	1.331 (4)
C1—C6	1.409 (5)	C10—O4	1.440 (5)
C1—C9	1.475 (5)	C2—H2	0.9802
C2—C3	1.365 (5)	C3—H3	1.0375
C3—C4	1.380 (6)	C4—H4	1.0097
C4—C5	1.368 (5)	C5—H5	1.0250
C5—C6	1.394 (5)	C8—H8A	1.0646
C6—N1	1.399 (5)	C8—H8B	0.9558
C7—O2	1.224 (4)	C10—H10A	0.9600
C7—N1	1.351 (5)	C10—H10B	0.9600
C7—C8	1.493 (5)	C10—H10C	0.9600
C8—O1	1.412 (5)	N1—H1N	0.8989
C9—O3	1.205 (4)	O1—H1	0.8986

C2—C1—C6	118.7 (3)	C2—C3—H3	119.7
C2—C1—C9	120.2 (3)	C4—C3—H3	121.5
C6—C1—C9	121.1 (3)	C5—C4—H4	120.6
C3—C2—C1	122.1 (4)	C3—C4—H4	117.8
C2—C3—C4	118.8 (3)	C4—C5—H5	119.0
C5—C4—C3	121.1 (4)	C6—C5—H5	120.4
C4—C5—C6	120.5 (4)	O1—C8—H8A	107.8
C5—C6—N1	121.7 (3)	C7—C8—H8A	109.4
C5—C6—C1	118.8 (3)	O1—C8—H8B	106.0
N1—C6—C1	119.5 (3)	C7—C8—H8B	108.0
O2—C7—N1	124.8 (3)	H8A—C8—H8B	112.4
O2—C7—C8	120.7 (3)	O4—C10—H10A	109.5
N1—C7—C8	114.5 (3)	O4—C10—H10B	109.5
O1—C8—C7	113.3 (3)	H10A—C10—H10B	109.5
O3—C9—O4	121.4 (3)	O4—C10—H10C	109.5
O3—C9—C1	126.0 (3)	H10A—C10—H10C	109.5
O4—C9—C1	112.6 (3)	H10B—C10—H10C	109.5
C7—N1—C6	129.6 (3)	C7—N1—H1N	116.6
C9—O4—C10	116.1 (3)	C6—N1—H1N	112.8
C3—C2—H2	118.6	C8—O1—H1	111.0
C1—C2—H2	119.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.90	1.95	2.669 (4)	136
O1—H1···O2ⁱ	0.90	1.91	2.758 (4)	157

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₄
M_r	209.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	3.938 (2), 8.808 (4), 27.94 (4)
V (Å³)	969.1 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.60 × 0.13 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7794, 1107, 846
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.127, 1.12
No. of reflections	1107
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: COLLECT (Nonius, 1999), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.90	1.95	2.669 (4)	136
O1—H1···O2ⁱ	0.90	1.91	2.758 (4)	157

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

NK is grateful to the Pakistan Science Foundation for financial assistance for the research work. The Swedish Research Council (VR) is acknowledged for providing funding for the diffractometer.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science CrossRef CAS IUCr Journals Google Scholar
Iacobelli, J., Uskokovic, M. & Wenner, W. (1965). J. Heterocycl. Chem, 2, 323–325. CrossRef CAS Google Scholar
Kenichi, O., Yoshihisa, Y., Toyonari, O., Toru, I. & Yoshio, I. (1985). J. Med. Chem. 28, 568–576. PubMed Web of Science Google Scholar
Lyle, F. R. (1985a). US Patent 5 973 257. Google Scholar
Lyle, F. R. (1985b). Chem. Abstr. 65, 2870. Google Scholar
Mhaske, S. B. & Argade, N. P. (2006). Tetrahedron, 62, 9787–9826. Web of Science CrossRef CAS Google Scholar
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uskokovic, M., Iacobelli, J., Toome, V. & Wenner, W. (1964). J. Org. Chem. 29, 582–584. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
Xia, Y., Yang, Z. Y., Hour, M. J., Kuo, S. C., Xia, P., Bastow, K. F., Nakanishi, Y., Nampoothiri, P., Hackl, T., Hamel, E. & Lee, K. H. (2001). Bioorg. Med. Chem. Lett. 11, 1193–1196. Web of Science CrossRef PubMed CAS Google Scholar