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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1940.
Published online 2010 July 7. doi:  10.1107/S1600536810026024
PMCID: PMC3007263

Propane-1,3-diyl bis­(4-amino­benzoate)

Abstract

Mol­ecules of the title compound, C17H18N2O4, lie on a twofold rotation axis that passes through the central methyl­ene C atom. The mol­ecules adopt a ‘V’ shape and the trimethyl­ene unit assumes a gauchegauche conformation. The amino N atom shows a nonplanar coordination. Adjacent mol­ecules are connected by N—H(...)O hydrogen bonds into chains running along [001]. Furthermore, N—H(...)N hydrogen bonds connect these chains into a three-dimensional network.

Related literature

For the crystal structure of 1,3-propandiyl-bis­(benzoate), see: Pérez & Brisse (1977 [triangle]).

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Object name is e-66-o1940-scheme1.jpg

Experimental

Crystal data

  • C17H18N2O4
  • M r = 314.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1940-efi1.jpg
  • a = 23.725 (5) Å
  • b = 4.5109 (9) Å
  • c = 8.2171 (17) Å
  • β = 107.173 (3)°
  • V = 840.2 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.35 × 0.35 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 3936 measured reflections
  • 1082 independent reflections
  • 788 reflections with I > 2σ(I)
  • R int = 0.090

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.109
  • S = 0.96
  • 1082 reflections
  • 113 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026024/bt5289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026024/bt5289Isup2.hkl

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

Acknowledgments

The authors thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The chemical is a commercially available chemical that should be compable of condensing with carbonyl compounds to yield Schff bases; its special feature is its trimethylene portion, which assumes a V shape. The C17H18N2O4 molecule (Scheme I) lies on a twofold rotation axis that passes through the central methylene carbon atom; this symmetry element relates one 4-aminobenzoate unit to the other. The molecule assumes a V shape and the trimethylene portion assumes a gauchegauche conformation. The amino nitrogen atom shows non-planar coordination (Fig. 1). Adjacent molecules are connected by N–H···O and N–H···N shydrogen bonds to form a three-dimensional network.

Experimental

The compound was returned unchanged but in a crystalline form in an unsuccessful condensation with o-vanillin in ethanol medium.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95–0.99 Å, U(H) 1.2U(C)] and were included in the refinement in the riding model approximation. The amino H-atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N–H 0.86±0.01 Å. 822 Friedel pairs were merged.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C17H18N2O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H18N2O4F(000) = 332
Mr = 314.33Dx = 1.242 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 915 reflections
a = 23.725 (5) Åθ = 2.6–26.8°
b = 4.5109 (9) ŵ = 0.09 mm1
c = 8.2171 (17) ÅT = 100 K
β = 107.173 (3)°Plate, yellow
V = 840.2 (3) Å30.35 × 0.35 × 0.02 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer788 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.090
graphiteθmax = 27.5°, θmin = 1.8°
ω scansh = −30→29
3936 measured reflectionsk = −5→5
1082 independent reflectionsl = −10→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 0.96w = 1/[σ2(Fo2) + (0.0523P)2] where P = (Fo2 + 2Fc2)/3
1082 reflections(Δ/σ)max = 0.001
113 parametersΔρmax = 0.24 e Å3
3 restraintsΔρmin = −0.24 e Å3

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

xyzUiso*/UeqOcc. (<1)
O10.42724 (7)0.4987 (4)0.0488 (2)0.0262 (5)
O20.35969 (8)0.7580 (5)−0.1476 (2)0.0304 (5)
N10.29701 (11)1.0783 (6)0.5367 (3)0.0298 (6)
C10.50000.1862 (10)0.00000.0279 (10)
H1A0.50950.0569−0.08570.033*0.50
H1B0.49050.05690.08570.033*0.50
C20.44676 (11)0.3705 (7)−0.0862 (3)0.0263 (7)
H2A0.45720.5279−0.15620.032*
H2B0.41530.2454−0.16090.032*
C30.38135 (11)0.6876 (7)0.0010 (3)0.0244 (7)
C40.36179 (11)0.7924 (7)0.1432 (3)0.0228 (6)
C50.31600 (11)0.9969 (7)0.1134 (3)0.0260 (7)
H50.29911.07210.00160.031*
C60.29486 (12)1.0917 (7)0.2423 (3)0.0286 (7)
H60.26311.22890.21870.034*
C70.31969 (11)0.9879 (7)0.4094 (3)0.0252 (7)
C80.36569 (11)0.7851 (8)0.4393 (3)0.0295 (7)
H80.38300.71230.55140.035*
C90.38646 (11)0.6885 (8)0.3103 (3)0.0282 (7)
H90.41790.54950.33380.034*
H110.3137 (17)1.032 (12)0.641 (2)0.098 (16)*
H120.2748 (10)1.233 (4)0.519 (3)0.025 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0204 (9)0.0351 (12)0.0206 (9)0.0041 (10)0.0021 (7)0.0031 (9)
O20.0239 (10)0.0453 (13)0.0165 (9)0.0042 (10)−0.0024 (7)0.0029 (10)
N10.0272 (14)0.0364 (17)0.0227 (13)0.0056 (12)0.0025 (11)0.0016 (12)
C10.021 (2)0.030 (3)0.029 (2)0.0000.0034 (16)0.000
C20.0205 (13)0.0329 (17)0.0243 (14)−0.0040 (13)0.0046 (11)−0.0024 (13)
C30.0172 (13)0.0302 (17)0.0224 (13)−0.0048 (13)0.0005 (11)0.0009 (13)
C40.0163 (12)0.0304 (17)0.0183 (12)−0.0025 (12)−0.0001 (10)0.0023 (11)
C50.0190 (13)0.0322 (17)0.0193 (13)−0.0007 (14)−0.0058 (11)0.0043 (13)
C60.0191 (14)0.0368 (19)0.0236 (14)0.0029 (13)−0.0031 (12)0.0038 (13)
C70.0186 (13)0.0335 (18)0.0202 (13)−0.0060 (14)0.0006 (10)0.0005 (13)
C80.0218 (14)0.043 (2)0.0179 (13)0.0039 (14)−0.0026 (11)0.0090 (14)
C90.0181 (14)0.0397 (19)0.0237 (14)0.0030 (14)0.0012 (11)0.0050 (14)

Geometric parameters (Å, °)

O1—C31.347 (3)C3—C41.457 (4)
O1—C21.444 (3)C4—C51.391 (4)
O2—C31.219 (3)C4—C91.405 (3)
N1—C71.372 (3)C5—C61.368 (4)
N1—H110.858 (10)C5—H50.9500
N1—H120.861 (10)C6—C71.405 (4)
C1—C21.503 (4)C6—H60.9500
C1—C2i1.503 (4)C7—C81.389 (4)
C1—H1A0.9900C8—C91.365 (4)
C1—H1B0.9900C8—H80.9500
C2—H2A0.9900C9—H90.9500
C2—H2B0.9900
C3—O1—C2116.39 (19)C5—C4—C9118.1 (2)
C7—N1—H11121 (3)C5—C4—C3119.4 (2)
C7—N1—H12118.1 (19)C9—C4—C3122.4 (2)
H11—N1—H12116 (4)C6—C5—C4121.1 (2)
C2—C1—C2i112.9 (4)C6—C5—H5119.4
C2—C1—H1A109.0C4—C5—H5119.4
C2i—C1—H1A109.0C5—C6—C7120.6 (3)
C2—C1—H1B109.0C5—C6—H6119.7
C2i—C1—H1B109.0C7—C6—H6119.7
H1A—C1—H1B107.8N1—C7—C8121.7 (2)
O1—C2—C1105.94 (18)N1—C7—C6120.0 (3)
O1—C2—H2A110.5C8—C7—C6118.2 (2)
C1—C2—H2A110.5C9—C8—C7121.2 (3)
O1—C2—H2B110.5C9—C8—H8119.4
C1—C2—H2B110.5C7—C8—H8119.4
H2A—C2—H2B108.7C8—C9—C4120.7 (3)
O2—C3—O1121.5 (2)C8—C9—H9119.7
O2—C3—C4125.4 (3)C4—C9—H9119.7
O1—C3—C4113.1 (2)
C3—O1—C2—C1176.5 (2)C3—C4—C5—C6177.4 (3)
C2i—C1—C2—O1−71.92 (18)C4—C5—C6—C71.1 (4)
C2—O1—C3—O2−3.8 (4)C5—C6—C7—N1−178.2 (3)
C2—O1—C3—C4176.2 (2)C5—C6—C7—C8−0.6 (4)
O2—C3—C4—C5−2.2 (4)N1—C7—C8—C9177.6 (3)
O1—C3—C4—C5177.8 (3)C6—C7—C8—C90.1 (5)
O2—C3—C4—C9176.1 (3)C7—C8—C9—C40.1 (5)
O1—C3—C4—C9−4.0 (4)C5—C4—C9—C80.3 (4)
C9—C4—C5—C6−0.9 (4)C3—C4—C9—C8−177.9 (3)

Symmetry codes: (i) −x+1, y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H11···O2ii0.86 (1)2.15 (2)2.958 (3)157 (5)
N1—H12···N1iii0.86 (1)2.25 (1)3.104 (3)169 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5289).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Pérez, S. & Brisse, F. (1977). Acta Cryst. B33, 3259–3262.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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