2-[2-(3-Methyl­but­oxy)-5-nitro­benz­amido]­acetic acid dimethyl sulfoxide monosolvate

Yang, Y.-X.; Ng, S.W.

doi:10.1107/S1600536812027316

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2170

https://doi.org/10.1107/S1600536812027316

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2-[2-(3-Methylbutoxy)-5-nitrobenzamido]acetic acid dimethyl sulfoxide monosolvate

Yun-Xia Yang ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Polymer Materials of Gansu Province Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2012; accepted 16 June 2012; online 23 June 2012)

In the title compound, C₁₄H₁₈N₂O₆·C₂H₆OS, the –C(O)NHCH₂CO₂H and –O(CH₂)₂CH(CH₃)₂ substitutents of the aromatic ring are positioned such that the –NH– group is hydrogen-bond donor to the ether O atom of the other substituent. The dimethyl sulfoxide solvent molecule is linked to the carboxylic acid group by an O—H⋯O hydrogen bond.

Related literature

For background to this study, see: Shaginian et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₈N₂O₆·C₂H₆OS
M_r = 388.43
Triclinic, $[P \overline 1]$
a = 7.4603 (12) Å
b = 11.2881 (18) Å
c = 11.5861 (19) Å
α = 99.229 (3)°
β = 99.802 (3)°
γ = 93.487 (3)°
V = 945.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.27 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.945, T_max = 0.963
5211 measured reflections
3644 independent reflections
2558 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.144
S = 1.01
3644 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7	0.84 (1)	1.75 (1)	2.579 (3)	170 (3)
N1—H2⋯O4	0.87 (1)	1.97 (2)	2.656 (3)	135 (2)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027316/xu5567sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027316/xu5567Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027316/xu5567Isup3.cml

checkCIF report

Comment top

The title compound is one that is similar to those identified for a study of protein-protein interactions (Shaginian et al., 2009). It crystallizes from DMSO as a monosolvate (Scheme I, Fig. 1). The –C(O)NHCH₂CO₂H and –O(CH₂)₂CH(CH₃)₂ substitutents of the aromatic ring of C₁₄H₁₈N₂O₆^.DMSO are positioned such that the –NH– group is hydrogen-bond donor to the ether O of the other substituent. The solvent molecule is linked to the carboxylic acid by an O–H···O hydrogen bond (Table 1).

Related literature top

For background to this study, see: Shaginian et al. (2009).

Experimental top

2-(Isopentyloxy)-4-nitrobenzoic acid (0.51 g, 2 mmol) was dissolved in thionyl chloride (2 ml). The synthesis is based on that reported for 2-methoxy-4-nitrobenzoic acid. The mixture was heated for half an hour. The excess reactant was evaporated and the residue dissolved in dichloromethane (10 ml) for the subsequent coupling reaction.

To a solution of methyl 2-aminoacetate hydrochloride (0.26 g, 2.1 mmol) in dichloromethane (30 ml) and triethylamine (0.5 ml) was added the above acid chloride at 273 K. The mixture was stirred at room temperature for half an hour. The solvent was removed and the residue was dissolved in methanol (50 ml) containing lithium hydroxide hydrate (0.65 g, 10 mmol) dissolved in water (2 ml). The mixture was heated for 5 h. The residue after removal of most of the solvent was acidified with 10% hydrochloric acid to a pH of 3. Filtration afforded the product as a white solid (0.41 g, 70%). Crystals were grown in DMSO.

Structure description top

For background to this study, see: Shaginian et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₈N₂O₆^.DMSO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-[2-(3-Methylbutoxy)-5-nitrobenzamido]acetic acid dimethyl sulfoxide monosolvate top

Crystal data top

C₁₄H₁₈N₂O₆·C₂H₆OS	Z = 2
M_r = 388.43	F(000) = 412
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4603 (12) Å	Cell parameters from 3644 reflections
b = 11.2881 (18) Å	θ = 1.8–26.0°
c = 11.5861 (19) Å	µ = 0.21 mm⁻¹
α = 99.229 (3)°	T = 293 K
β = 99.802 (3)°	Prism, colorless
γ = 93.487 (3)°	0.27 × 0.24 × 0.18 mm
V = 945.1 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	3644 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.945, T_max = 0.963	k = −12→13
5211 measured reflections	l = −13→14

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0647P)²] where P = (F_o² + 2F_c²)/3
3644 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₆·C₂H₆OS	γ = 93.487 (3)°
M_r = 388.43	V = 945.1 (3) Å³
Triclinic, P1	Z = 2
a = 7.4603 (12) Å	Mo Kα radiation
b = 11.2881 (18) Å	µ = 0.21 mm⁻¹
c = 11.5861 (19) Å	T = 293 K
α = 99.229 (3)°	0.27 × 0.24 × 0.18 mm
β = 99.802 (3)°

Data collection top

Bruker SMART APEX diffractometer	3644 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2558 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.963	R_int = 0.035
5211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.32 e Å⁻³
3644 reflections	Δρ_min = −0.29 e Å⁻³
243 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.28957 (10)	−0.17297 (6)	0.17669 (6)	0.0234 (2)
O1	0.2603 (3)	−0.00955 (17)	0.47071 (18)	0.0255 (5)
O2	0.2747 (3)	0.14280 (17)	0.36944 (18)	0.0370 (6)
O3	0.1140 (3)	0.36605 (17)	0.72134 (17)	0.0262 (5)
O4	0.2827 (2)	0.47573 (16)	0.42855 (15)	0.0181 (4)
O5	0.1885 (3)	0.92011 (17)	0.80371 (18)	0.0297 (5)
O6	0.0932 (3)	0.77455 (18)	0.88517 (17)	0.0295 (5)
O7	0.3687 (3)	−0.15722 (17)	0.30829 (17)	0.0271 (5)
N1	0.2100 (3)	0.3040 (2)	0.5503 (2)	0.0187 (5)
N2	0.1524 (3)	0.8122 (2)	0.8040 (2)	0.0222 (6)
C1	0.2487 (4)	0.1034 (2)	0.4564 (2)	0.0208 (6)
C2	0.1965 (4)	0.1786 (2)	0.5629 (2)	0.0194 (6)
H2A	0.0725	0.1533	0.5692	0.023*
H2B	0.2772	0.1679	0.6347	0.023*
C3	0.1688 (4)	0.3899 (2)	0.6327 (2)	0.0167 (6)
C4	0.1942 (3)	0.5189 (2)	0.6155 (2)	0.0153 (6)
C5	0.2520 (3)	0.5602 (2)	0.5177 (2)	0.0155 (6)
C6	0.2746 (4)	0.6832 (2)	0.5155 (2)	0.0191 (6)
H6	0.3113	0.7095	0.4504	0.023*
C7	0.2429 (4)	0.7664 (2)	0.6094 (2)	0.0192 (6)
H7	0.2603	0.8486	0.6089	0.023*
C8	0.1850 (4)	0.7253 (2)	0.7040 (2)	0.0181 (6)
C9	0.1608 (3)	0.6042 (2)	0.7080 (2)	0.0153 (6)
H9	0.1217	0.5794	0.7731	0.018*
C10	0.3186 (4)	0.5110 (2)	0.3185 (2)	0.0181 (6)
H10A	0.4303	0.5641	0.3334	0.022*
H10B	0.2187	0.5524	0.2832	0.022*
C11	0.3368 (4)	0.3956 (2)	0.2372 (2)	0.0182 (6)
H11A	0.2246	0.3435	0.2253	0.022*
H11B	0.4346	0.3547	0.2757	0.022*
C12	0.3764 (4)	0.4145 (3)	0.1161 (2)	0.0232 (7)
H12	0.4864	0.4705	0.1289	0.028*
C13	0.4120 (4)	0.2954 (3)	0.0449 (3)	0.0322 (8)
H13A	0.4378	0.3084	−0.0307	0.048*
H13B	0.3061	0.2391	0.0328	0.048*
H13C	0.5146	0.2637	0.0878	0.048*
C14	0.2198 (4)	0.4682 (3)	0.0460 (3)	0.0283 (7)
H14A	0.1978	0.5432	0.0912	0.043*
H14B	0.1117	0.4133	0.0307	0.043*
H14C	0.2511	0.4820	−0.0280	0.043*
C15	0.3742 (5)	−0.0420 (3)	0.1283 (3)	0.0330 (8)
H15A	0.5024	−0.0447	0.1276	0.049*
H15B	0.3552	0.0286	0.1816	0.049*
H15C	0.3105	−0.0393	0.0496	0.049*
C16	0.0586 (4)	−0.1409 (3)	0.1671 (3)	0.0285 (7)
H16A	−0.0098	−0.2046	0.1910	0.043*
H16B	0.0083	−0.1345	0.0866	0.043*
H16C	0.0520	−0.0662	0.2185	0.043*
H1	0.295 (4)	−0.051 (2)	0.4133 (19)	0.035 (10)*
H2	0.242 (4)	0.323 (2)	0.4863 (16)	0.027 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0284 (4)	0.0195 (4)	0.0233 (4)	0.0026 (3)	0.0109 (3)	0.0000 (3)
O1	0.0410 (14)	0.0135 (11)	0.0255 (12)	0.0049 (10)	0.0135 (10)	0.0049 (9)
O2	0.0716 (18)	0.0176 (12)	0.0282 (12)	0.0052 (11)	0.0252 (12)	0.0055 (9)
O3	0.0385 (13)	0.0217 (11)	0.0219 (11)	0.0012 (10)	0.0145 (10)	0.0051 (9)
O4	0.0240 (11)	0.0174 (10)	0.0149 (10)	0.0030 (8)	0.0083 (8)	0.0034 (8)
O5	0.0378 (13)	0.0145 (11)	0.0364 (13)	0.0038 (10)	0.0104 (10)	−0.0012 (9)
O6	0.0344 (13)	0.0317 (13)	0.0230 (12)	−0.0004 (10)	0.0142 (10)	−0.0013 (9)
O7	0.0350 (13)	0.0226 (12)	0.0238 (11)	0.0060 (10)	0.0064 (9)	0.0019 (9)
N1	0.0255 (14)	0.0140 (12)	0.0190 (13)	0.0003 (10)	0.0092 (11)	0.0049 (10)
N2	0.0197 (13)	0.0208 (14)	0.0245 (14)	0.0040 (11)	0.0047 (11)	−0.0023 (11)
C1	0.0210 (16)	0.0204 (16)	0.0208 (16)	−0.0004 (13)	0.0026 (12)	0.0053 (13)
C2	0.0232 (16)	0.0152 (15)	0.0209 (15)	−0.0016 (12)	0.0066 (12)	0.0053 (12)
C3	0.0160 (14)	0.0173 (15)	0.0169 (14)	0.0025 (12)	0.0028 (11)	0.0032 (12)
C4	0.0121 (14)	0.0172 (15)	0.0162 (14)	0.0019 (11)	0.0004 (11)	0.0033 (11)
C5	0.0106 (14)	0.0202 (15)	0.0145 (14)	0.0019 (11)	0.0003 (11)	0.0016 (11)
C6	0.0186 (15)	0.0209 (16)	0.0182 (15)	0.0006 (12)	0.0022 (12)	0.0066 (12)
C7	0.0216 (16)	0.0126 (14)	0.0243 (16)	0.0041 (12)	0.0038 (12)	0.0055 (12)
C8	0.0163 (15)	0.0199 (15)	0.0169 (15)	0.0025 (12)	0.0026 (11)	−0.0004 (12)
C9	0.0100 (13)	0.0210 (15)	0.0154 (14)	0.0018 (11)	0.0027 (11)	0.0046 (11)
C10	0.0210 (15)	0.0214 (15)	0.0130 (14)	0.0017 (12)	0.0055 (11)	0.0040 (11)
C11	0.0153 (15)	0.0195 (15)	0.0206 (15)	0.0020 (12)	0.0040 (11)	0.0053 (12)
C12	0.0207 (16)	0.0300 (18)	0.0195 (16)	−0.0003 (13)	0.0075 (12)	0.0029 (13)
C13	0.0303 (18)	0.045 (2)	0.0211 (16)	0.0127 (16)	0.0077 (14)	−0.0016 (14)
C14	0.0378 (19)	0.0287 (18)	0.0197 (16)	0.0055 (15)	0.0064 (14)	0.0058 (13)
C15	0.039 (2)	0.0322 (19)	0.0277 (18)	−0.0078 (16)	0.0114 (15)	0.0055 (14)
C16	0.0275 (18)	0.0353 (19)	0.0238 (16)	0.0034 (14)	0.0088 (13)	0.0041 (14)

Geometric parameters (Å, º) top

S1—O7	1.516 (2)	C7—H7	0.9300
S1—C16	1.771 (3)	C8—C9	1.378 (4)
S1—C15	1.781 (3)	C9—H9	0.9300
O1—C1	1.317 (3)	C10—C11	1.507 (4)
O1—H1	0.838 (10)	C10—H10A	0.9700
O2—C1	1.205 (3)	C10—H10B	0.9700
O3—C3	1.230 (3)	C11—C12	1.526 (4)
O4—C5	1.348 (3)	C11—H11A	0.9700
O4—C10	1.457 (3)	C11—H11B	0.9700
O5—N2	1.232 (3)	C12—C14	1.521 (4)
O6—N2	1.228 (3)	C12—C13	1.524 (4)
N1—C3	1.336 (3)	C12—H12	0.9800
N1—C2	1.445 (3)	C13—H13A	0.9600
N1—H2	0.873 (10)	C13—H13B	0.9600
N2—C8	1.457 (3)	C13—H13C	0.9600
C1—C2	1.504 (4)	C14—H14A	0.9600
C2—H2A	0.9700	C14—H14B	0.9600
C2—H2B	0.9700	C14—H14C	0.9600
C3—C4	1.505 (4)	C15—H15A	0.9600
C4—C9	1.389 (3)	C15—H15B	0.9600
C4—C5	1.414 (3)	C15—H15C	0.9600
C5—C6	1.394 (4)	C16—H16A	0.9600
C6—C7	1.381 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.379 (4)

O7—S1—C16	106.07 (13)	O4—C10—H10A	110.6
O7—S1—C15	105.75 (13)	C11—C10—H10A	110.6
C16—S1—C15	98.07 (15)	O4—C10—H10B	110.6
C1—O1—H1	112 (2)	C11—C10—H10B	110.6
C5—O4—C10	119.82 (19)	H10A—C10—H10B	108.7
C3—N1—C2	121.4 (2)	C10—C11—C12	113.6 (2)
C3—N1—H2	119.6 (19)	C10—C11—H11A	108.8
C2—N1—H2	119.0 (19)	C12—C11—H11A	108.8
O6—N2—O5	123.2 (2)	C10—C11—H11B	108.8
O6—N2—C8	118.6 (2)	C12—C11—H11B	108.8
O5—N2—C8	118.2 (2)	H11A—C11—H11B	107.7
O2—C1—O1	125.2 (3)	C14—C12—C13	109.7 (2)
O2—C1—C2	123.4 (2)	C14—C12—C11	111.6 (2)
O1—C1—C2	111.4 (2)	C13—C12—C11	110.1 (2)
N1—C2—C1	109.4 (2)	C14—C12—H12	108.4
N1—C2—H2A	109.8	C13—C12—H12	108.4
C1—C2—H2A	109.8	C11—C12—H12	108.4
N1—C2—H2B	109.8	C12—C13—H13A	109.5
C1—C2—H2B	109.8	C12—C13—H13B	109.5
H2A—C2—H2B	108.2	H13A—C13—H13B	109.5
O3—C3—N1	121.8 (2)	C12—C13—H13C	109.5
O3—C3—C4	120.2 (2)	H13A—C13—H13C	109.5
N1—C3—C4	118.1 (2)	H13B—C13—H13C	109.5
C9—C4—C5	118.1 (2)	C12—C14—H14A	109.5
C9—C4—C3	115.2 (2)	C12—C14—H14B	109.5
C5—C4—C3	126.7 (2)	H14A—C14—H14B	109.5
O4—C5—C6	122.6 (2)	C12—C14—H14C	109.5
O4—C5—C4	117.1 (2)	H14A—C14—H14C	109.5
C6—C5—C4	120.3 (2)	H14B—C14—H14C	109.5
C7—C6—C5	120.5 (2)	S1—C15—H15A	109.5
C7—C6—H6	119.7	S1—C15—H15B	109.5
C5—C6—H6	119.7	H15A—C15—H15B	109.5
C8—C7—C6	118.8 (2)	S1—C15—H15C	109.5
C8—C7—H7	120.6	H15A—C15—H15C	109.5
C6—C7—H7	120.6	H15B—C15—H15C	109.5
C9—C8—C7	121.9 (2)	S1—C16—H16A	109.5
C9—C8—N2	118.8 (2)	S1—C16—H16B	109.5
C7—C8—N2	119.3 (2)	H16A—C16—H16B	109.5
C8—C9—C4	120.4 (2)	S1—C16—H16C	109.5
C8—C9—H9	119.8	H16A—C16—H16C	109.5
C4—C9—H9	119.8	H16B—C16—H16C	109.5
O4—C10—C11	105.9 (2)

C3—N1—C2—C1	179.2 (2)	C4—C5—C6—C7	0.8 (4)
O2—C1—C2—N1	−8.4 (4)	C5—C6—C7—C8	−1.3 (4)
O1—C1—C2—N1	172.2 (2)	C6—C7—C8—C9	1.0 (4)
C2—N1—C3—O3	−1.5 (4)	C6—C7—C8—N2	179.6 (2)
C2—N1—C3—C4	177.4 (2)	O6—N2—C8—C9	−4.5 (4)
O3—C3—C4—C9	3.1 (4)	O5—N2—C8—C9	174.3 (2)
N1—C3—C4—C9	−175.9 (2)	O6—N2—C8—C7	176.8 (3)
O3—C3—C4—C5	−178.5 (3)	O5—N2—C8—C7	−4.3 (4)
N1—C3—C4—C5	2.5 (4)	C7—C8—C9—C4	−0.1 (4)
C10—O4—C5—C6	−8.0 (4)	N2—C8—C9—C4	−178.7 (2)
C10—O4—C5—C4	171.8 (2)	C5—C4—C9—C8	−0.5 (4)
C9—C4—C5—O4	−179.6 (2)	C3—C4—C9—C8	178.0 (2)
C3—C4—C5—O4	2.1 (4)	C5—O4—C10—C11	−177.2 (2)
C9—C4—C5—C6	0.2 (4)	O4—C10—C11—C12	−179.6 (2)
C3—C4—C5—C6	−178.1 (3)	C10—C11—C12—C14	−63.7 (3)
O4—C5—C6—C7	−179.5 (2)	C10—C11—C12—C13	174.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7	0.84 (1)	1.75 (1)	2.579 (3)	170 (3)
N1—H2···O4	0.87 (1)	1.97 (2)	2.656 (3)	135 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₆·C₂H₆OS
M_r	388.43
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4603 (12), 11.2881 (18), 11.5861 (19)
α, β, γ (°)	99.229 (3), 99.802 (3), 93.487 (3)
V (Å³)	945.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.27 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	5211, 3644, 2558
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.144, 1.01
No. of reflections	3644
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7	0.84 (1)	1.75 (1)	2.579 (3)	170 (3)
N1—H2···O4	0.87 (1)	1.97 (2)	2.656 (3)	135 (2)

Acknowledgements

We thank Northeast Normal University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shaginian, A., Whitby, L. R., Hong, S., Hwang, I., Farooqi, B., Searcey, M., Chen, J., Vogt, P. K. & Boger, D. L. (2009). J. Am. Chem. Soc. 131, 5564–5572. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-[2-(3-Methyl­but­­oxy)-5-nitro­benz­amido]­acetic acid di­methyl sulfoxide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[2-(3-Methylbutoxy)-5-nitrobenzamido]acetic acid dimethyl sulfoxide monosolvate