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Acta Cryst. (2010). E66, o1940    [ doi:10.1107/S1600536810026024 ]

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

M. Raza Shah and S. W. Ng

Abstract top

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 gauche-gauche 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.

Comment top

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 gauche–gauche 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.

Related literature top

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

Experimental top

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

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C17H18N2O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Propane-1,3-diyl bis(4-aminobenzoate) top
Crystal data top
C17H18N2O4F(000) = 332
Mr = 314.33Dx = 1.242 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		788 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 top
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 = 0.96 w = 1/[σ2(Fo2) + (0.0523P)2]
where P = (Fo2 + 2Fc2)/3
1082 reflections(Δ/σ)max = 0.001
113 parametersΔρmax = 0.24 e Å−3
3 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C17H18N2O4V = 840.2 (3) Å3
Mr = 314.33Z = 2
Monoclinic, C2Mo Kα radiation
a = 23.725 (5) ŵ = 0.09 mm−1
b = 4.5109 (9) ÅT = 100 K
c = 8.2171 (17) Å0.35 × 0.35 × 0.02 mm
β = 107.173 (3)°
Data collection top
Bruker SMART APEX
diffractometer		788 reflections with I > 2σ(I)
3936 measured reflectionsRint = 0.090
1082 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109Δρmax = 0.24 e Å−3
S = 0.96Δρmin = −0.24 e Å−3
1082 reflectionsAbsolute structure: ?
113 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.86 (1)2.15 (2)2.958 (3)157 (5)
N1—H12···N1ii0.86 (1)2.25 (1)3.104 (3)169 (2)
Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y+1/2, −z+1.
Acknowledgements top

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

references
References top

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.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.