2-(2-Eth­oxy-2-oxoacetamido)­benzoic acid

Yu, M.C.; Wang, L.L.; Wang, L.Y.; Wu, Z.Y.

doi:10.1107/S2414314620006033

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 5| May 2020| x200603

https://doi.org/10.1107/S2414314620006033

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2-(2-Ethoxy-2-oxoacetamido)benzoic acid

MingChao Yu,^a LinLin Wang,^a LingYang Wang ^a and ZhiYong Wu ^a ^*

^aSchool of Medicine and Pharmacy and College of Marine Life Science, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China
^*Correspondence e-mail: wuzy@ouc.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 1 April 2020; accepted 2 May 2020; online 6 May 2020)

The title compound, C₁₁H₁₁NO₅, has a nearly planar geometry. In the crystal, the molecules are assembled into chains parallel to the [ $[\overline{1}]$ 11] direction by O—H⋯O and C—H⋯O hydrogen bonds.

Keywords: crystal structure; oxamide derivative; hydrogen bonds.

CCDC reference: 2000864

Structure description

Oxamide derivatives are of considerable current interest because of their DNA-binding properties and cytotoxic activity (Martínez-Martínez et al., 1998 ; Li et al., 2012 ; Yue et al., 2012 ; Zheng et al., 2012 ). As part of our studies in this area, we report the structure of the title compound herein.

The asymmetric unit contains one title compound adopting the expected transoid conformation (Fig. 1). The molecule has an almost planar geometry except for the terminal methyl group; atom C11 deviates by 0.388 (3) Å from the mean plane of other atoms. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.96 (3)	1.67 (3)	2.6274 (16)	176 (2)
N1—H1A⋯O2	0.93 (2)	1.92 (2)	2.6574 (15)	135.1 (16)
C5—H5⋯O3	0.948 (19)	2.230 (18)	2.866 (2)	123.7 (14)
C5—H5⋯O3ⁱⁱ	0.948 (19)	2.36 (2)	3.1107 (19)	135.9 (14)
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y, -z+1.

Figure 1
Molecular structure of the title compound with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds (Table 1

) are indicated by dashed lines.

In crystal, pairs of molecules are linked by O—H⋯O hydrogen bonds (Table 1) into inversion dimers characterized by an R₂²(8) motif (Fig. 2). The dimers are linked by further C—H⋯O hydrogen bonds with an R₂²(12) motif, giving rise to a chain extending along the [ $[\overline{1}]$ 11] direction.

Figure 2
A one-dimensional hydrogen-bonded chain along [ $[\overline{1}]$ 11]. Hydrogen bonds (Table 1

) are indicated by dashed lines. H atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) −x, 1 − y, 2 − z; (ii) 1 − x, −y, 1 − z.

Synthesis and crystallization

The title compound was synthesized using a literature method (Matović, 2005 ). Ethyl chlorooxoacetate (10 mmol, 1.13 ml) in 10 ml of tetrahydrofuran (THF) was added dropwise to a 10 ml THF solution containing 2-aminobenzoic acid (10 mmol, 1.37 g) at 273 K. The resulting solution was stirred for 2 h. The solution was concentrated under vacuum and the compound was precipitated as a yellowish powder then washed with ether and dried under vacuum. Well-shaped yellowish single crystals were obtained by slow evaporation of an ethanol solution of the recrystallized product. Yield: 55%. Analysis calculated for C₁₁H₁₁NO₅: C, 55.70; H, 4.67; N, 5.90%. Found: C, 55.77; H, 4.64; N, 5.92%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₅
M_r	237.21
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	4.8774 (13), 9.470 (3), 12.719 (3)
α, β, γ (°)	106.784 (7), 97.222 (7), 92.444 (8)
V (Å³)	556.1 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.73 × 0.24 × 0.19

Data collection
Diffractometer	Bruker APEX area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002 )
No. of measured, independent and observed [I > 2σ(I)] reflections	8969, 2557, 2016
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 1.06
No. of reflections	2557
No. of parameters	198
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27
Computer programs: SMART and SAINT (Bruker, 2002), XP in SHELXTL and SHELXS97 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ) and publCIF (Westrip, 2010).

Structural data

CCDC reference: 2000864

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620006033/xu4040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620006033/xu4040Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620006033/xu4040Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

2-(2-Ethoxy-2-oxoacetamido)benzoic acid top

Crystal data top

C₁₁H₁₁NO₅	Z = 2
M_r = 237.21	F(000) = 248
Triclinic, P1	D_x = 1.417 Mg m⁻³
a = 4.8774 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.470 (3) Å	Cell parameters from 4983 reflections
c = 12.719 (3) Å	θ = 2.4–27.7°
α = 106.784 (7)°	µ = 0.11 mm⁻¹
β = 97.222 (7)°	T = 296 K
γ = 92.444 (8)°	Plate, light yellow
V = 556.1 (3) Å³	0.73 × 0.24 × 0.19 mm

Data collection top

Bruker APEX area detector diffractometer	2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
ω scans	θ_max = 27.7°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
	k = −12→12
8969 measured reflections	l = −16→16
2557 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	All H-atom parameters refined
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0728P)² + 0.0917P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2557 reflections	Δρ_max = 0.24 e Å⁻³
198 parameters	Δρ_min = −0.27 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were found in a difference Fourier map and refined freely.

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

	x	y	z	U_iso*/U_eq
O1	0.2576 (3)	0.38020 (16)	1.03091 (9)	0.0681 (4)
O2	0.0551 (2)	0.41447 (12)	0.87522 (8)	0.0535 (3)
O3	0.2481 (3)	0.12887 (17)	0.50560 (9)	0.0830 (5)
O4	−0.2254 (3)	0.38059 (15)	0.60001 (9)	0.0660 (4)
O5	−0.1328 (2)	0.27460 (13)	0.42790 (8)	0.0557 (3)
N1	0.1791 (2)	0.24475 (13)	0.68396 (9)	0.0422 (3)
C1	0.3864 (3)	0.23438 (16)	0.86482 (11)	0.0420 (3)
C2	0.5692 (3)	0.1711 (2)	0.92768 (13)	0.0551 (4)
C3	0.7340 (4)	0.0645 (2)	0.87854 (15)	0.0602 (4)
C4	0.7185 (3)	0.01962 (18)	0.76469 (14)	0.0533 (4)
C5	0.5376 (3)	0.07796 (17)	0.70010 (12)	0.0463 (3)
C6	0.3673 (3)	0.18576 (15)	0.74833 (10)	0.0385 (3)
C7	0.2187 (3)	0.35013 (17)	0.92252 (11)	0.0456 (3)
C8	0.1306 (3)	0.21176 (16)	0.57239 (10)	0.0451 (3)
C9	−0.1000 (3)	0.29967 (16)	0.53589 (11)	0.0446 (3)
C10	−0.3469 (4)	0.3514 (2)	0.38191 (15)	0.0622 (5)
C11	−0.3098 (6)	0.3297 (3)	0.26382 (17)	0.0828 (7)
H1	0.139 (5)	0.455 (3)	1.061 (2)	0.099 (8)*
H1A	0.065 (4)	0.311 (2)	0.7222 (17)	0.070 (6)*
H2	0.581 (4)	0.206 (2)	1.0049 (19)	0.078 (6)*
H3	0.856 (4)	0.025 (2)	0.9243 (18)	0.081 (6)*
H4	0.836 (4)	−0.0499 (19)	0.7304 (16)	0.058 (5)*
H5	0.532 (4)	0.046 (2)	0.6220 (16)	0.054 (4)*
H10A	−0.321 (4)	0.452 (2)	0.4258 (18)	0.077 (6)*
H10B	−0.517 (4)	0.307 (2)	0.3905 (17)	0.075 (6)*
H11A	−0.121 (6)	0.375 (3)	0.260 (2)	0.114 (9)*
H11B	−0.326 (5)	0.229 (3)	0.224 (2)	0.109 (9)*
H11C	−0.457 (5)	0.377 (3)	0.230 (2)	0.096 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0815 (8)	0.0954 (9)	0.0244 (5)	0.0438 (7)	0.0077 (5)	0.0081 (5)
O2	0.0659 (7)	0.0677 (7)	0.0261 (5)	0.0287 (5)	0.0102 (4)	0.0077 (4)
O3	0.1083 (10)	0.1073 (10)	0.0320 (6)	0.0657 (9)	0.0163 (6)	0.0079 (6)
O4	0.0726 (8)	0.0869 (9)	0.0377 (6)	0.0387 (6)	0.0092 (5)	0.0122 (6)
O5	0.0683 (7)	0.0699 (7)	0.0289 (5)	0.0181 (5)	0.0034 (5)	0.0144 (5)
N1	0.0479 (6)	0.0527 (7)	0.0251 (5)	0.0165 (5)	0.0087 (4)	0.0070 (5)
C1	0.0421 (7)	0.0520 (8)	0.0306 (7)	0.0093 (6)	0.0066 (5)	0.0089 (6)
C2	0.0592 (9)	0.0720 (10)	0.0338 (7)	0.0177 (7)	0.0036 (6)	0.0150 (7)
C3	0.0601 (10)	0.0710 (10)	0.0518 (9)	0.0246 (8)	0.0020 (7)	0.0218 (8)
C4	0.0539 (9)	0.0549 (9)	0.0525 (9)	0.0201 (7)	0.0124 (7)	0.0136 (7)
C5	0.0509 (8)	0.0510 (8)	0.0364 (7)	0.0127 (6)	0.0110 (6)	0.0089 (6)
C6	0.0401 (6)	0.0452 (7)	0.0299 (6)	0.0072 (5)	0.0073 (5)	0.0093 (5)
C7	0.0493 (8)	0.0588 (8)	0.0261 (6)	0.0117 (6)	0.0062 (5)	0.0072 (6)
C8	0.0543 (8)	0.0521 (8)	0.0269 (6)	0.0143 (6)	0.0090 (5)	0.0060 (5)
C9	0.0510 (8)	0.0505 (8)	0.0294 (6)	0.0078 (6)	0.0043 (5)	0.0076 (6)
C10	0.0689 (11)	0.0728 (12)	0.0470 (9)	0.0097 (9)	−0.0051 (8)	0.0260 (8)
C11	0.1075 (18)	0.0977 (17)	0.0459 (10)	0.0012 (14)	−0.0099 (10)	0.0354 (11)

Geometric parameters (Å, º) top

O1—C7	1.3116 (17)	C2—H2	0.94 (2)
O1—H1	0.96 (3)	C3—C4	1.377 (2)
O2—C7	1.2258 (17)	C3—H3	0.94 (2)
O3—C8	1.2007 (18)	C4—C5	1.371 (2)
O4—C9	1.1963 (18)	C4—H4	0.939 (18)
O5—C9	1.3122 (16)	C5—C6	1.3955 (19)
O5—C10	1.456 (2)	C5—H5	0.948 (19)
N1—C8	1.3493 (17)	C8—C9	1.532 (2)
N1—C6	1.3944 (18)	C10—C11	1.491 (3)
N1—H1A	0.93 (2)	C10—H10A	0.95 (2)
C1—C2	1.392 (2)	C10—H10B	0.95 (2)
C1—C6	1.4084 (18)	C11—H11A	1.01 (3)
C1—C7	1.474 (2)	C11—H11B	0.93 (3)
C2—C3	1.374 (2)	C11—H11C	0.98 (3)

C7—O1—H1	108.9 (15)	C5—C6—C1	118.68 (13)
C9—O5—C10	116.37 (13)	O2—C7—O1	121.64 (13)
C8—N1—C6	128.24 (12)	O2—C7—C1	124.02 (12)
C8—N1—H1A	115.5 (12)	O1—C7—C1	114.35 (12)
C6—N1—H1A	116.1 (12)	O3—C8—N1	127.84 (14)
C2—C1—C6	119.03 (13)	O3—C8—C9	121.08 (13)
C2—C1—C7	118.80 (12)	N1—C8—C9	111.06 (11)
C6—C1—C7	122.16 (12)	O4—C9—O5	126.54 (14)
C3—C2—C1	121.37 (14)	O4—C9—C8	122.79 (12)
C3—C2—H2	121.1 (13)	O5—C9—C8	110.66 (12)
C1—C2—H2	117.5 (13)	O5—C10—C11	106.64 (18)
C2—C3—C4	119.29 (15)	O5—C10—H10A	106.7 (13)
C2—C3—H3	118.4 (13)	C11—C10—H10A	113.3 (13)
C4—C3—H3	122.3 (13)	O5—C10—H10B	105.1 (12)
C5—C4—C3	120.89 (14)	C11—C10—H10B	113.6 (13)
C5—C4—H4	119.0 (11)	H10A—C10—H10B	110.7 (18)
C3—C4—H4	120.1 (11)	C10—C11—H11A	109.9 (15)
C4—C5—C6	120.72 (14)	C10—C11—H11B	111.3 (16)
C4—C5—H5	119.4 (11)	H11A—C11—H11B	109 (2)
C6—C5—H5	119.9 (11)	C10—C11—H11C	108.4 (15)
N1—C6—C5	121.55 (12)	H11A—C11—H11C	110 (2)
N1—C6—C1	119.77 (11)	H11B—C11—H11C	108 (2)

C6—C1—C2—C3	1.2 (2)	C2—C1—C7—O2	178.82 (14)
C7—C1—C2—C3	−178.93 (16)	C6—C1—C7—O2	−1.3 (2)
C1—C2—C3—C4	0.2 (3)	C2—C1—C7—O1	−1.2 (2)
C2—C3—C4—C5	−1.2 (3)	C6—C1—C7—O1	178.69 (13)
C3—C4—C5—C6	0.8 (3)	C6—N1—C8—O3	−3.3 (3)
C8—N1—C6—C5	−0.1 (2)	C6—N1—C8—C9	178.43 (13)
C8—N1—C6—C1	−179.63 (13)	C10—O5—C9—O4	−1.1 (2)
C4—C5—C6—N1	−178.99 (14)	C10—O5—C9—C8	179.88 (14)
C4—C5—C6—C1	0.5 (2)	O3—C8—C9—O4	178.26 (18)
C2—C1—C6—N1	178.03 (13)	N1—C8—C9—O4	−3.3 (2)
C7—C1—C6—N1	−1.9 (2)	O3—C8—C9—O5	−2.7 (2)
C2—C1—C6—C5	−1.5 (2)	N1—C8—C9—O5	175.70 (12)
C7—C1—C6—C5	178.62 (13)	C9—O5—C10—C11	169.35 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.96 (3)	1.67 (3)	2.6274 (16)	176 (2)
N1—H1A···O2	0.93 (2)	1.92 (2)	2.6574 (15)	135.1 (16)
C5—H5···O3	0.948 (19)	2.230 (18)	2.866 (2)	123.7 (14)
C5—H5···O3ⁱⁱ	0.948 (19)	2.36 (2)	3.1107 (19)	135.9 (14)

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y, −z+1.

Funding information

This work was supported by Shandong Province Key Research and Development Project (2018GSF118174), Qingdao People's Livelihood Science and Technology Project (18–6-1–95-nsh), and the NSFC–Shandong Joint Fund for Marine Science Research Centers (grant No. U1606403).

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