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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jun 23;68(Pt 7):o2170. doi: 10.1107/S1600536812027316

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

Yun-Xia Yang a, Seik Weng Ng b,c,*
PMCID: PMC3393976  PMID: 22798841

Abstract

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 ▶).graphic file with name e-68-o2170-scheme1.jpg

Experimental  

Crystal data  

  • C14H18N2O6·C2H6OS

  • M r = 388.43

  • Triclinic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.057

  • wR(F 2) = 0.144

  • S = 1.01

  • 3644 reflections

  • 243 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.29 e Å−3

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027316/xu5567sup1.cif

e-68-o2170-sup1.cif (18.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027316/xu5567Isup2.hkl

e-68-o2170-Isup2.hkl (178.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812027316/xu5567Isup3.cml

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

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)
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Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.20 to 1.5U(C).

The acid and amino H-atoms were located in a difference Fourier map, and were refined with distance restrainst of O–H 0.84±0.01 and N–H 0.84±0.01 Å; their temperature factors were freely refined.

Figures

Fig. 1.

Fig. 1.

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

Crystal data

C14H18N2O6·C2H6OS Z = 2
Mr = 388.43 F(000) = 412
Triclinic, P1 Dx = 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
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Data collection

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

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(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3
3644 reflections (Δ/σ)max = 0.001
243 parameters Δρmax = 0.32 e Å−3
2 restraints Δρmin = −0.29 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
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)*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Hydrogen-bond geometry (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5567).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  2. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. 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. [DOI] [PMC free article] [PubMed]
  4. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  5. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  6. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027316/xu5567sup1.cif

e-68-o2170-sup1.cif (18.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027316/xu5567Isup2.hkl

e-68-o2170-Isup2.hkl (178.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812027316/xu5567Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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