Methyl 2-(2-hydroxy-acetamido)benzoate.

The title compound, C(10)H(11)NO(4), was formed from 4,1-benzoxazepine-2,5(1H,3H)-dione and ammonia gas. Intra-molecular hydrogen bonding is present between the amide N-H group and the carbonyl O atom of the ester group. The crystal structure features inter-molecular 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 = 209.20

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.127

S = 1.12

1107 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H11NO4	F(000) = 440
Mr = 209.20	Dx = 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

Nonius KappaCCD diffractometer	Rint = 0.104
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 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 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(Fo2) + (0.0491P)2 + 0.4762P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1107 reflections	Δρmax = 0.18 e Å−3
137 parameters	Δρmin = −0.21 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .