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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1754.
Published online 2009 July 4. doi:  10.1107/S1600536809024696
PMCID: PMC2977371

Di-n-butyl 5-amino­isophthalate

Abstract

The title compound, C16H23NO4, is essentially planar except for the last two C atoms in each n-butyl group (r.m.s. deviation from the least-squares plane = 0.02 Å for 17 non-H atoms). In the crystal, inter­molecular N—H(...)O hydrogen bonds between the amine and carbonyl groups link the mol­ecules into one-dimensional chains.

Related literature

For the related structure of 5-amino­isophthalic acid hemihydrate, see: Dobson & Gerkin (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1754-scheme1.jpg

Experimental

Crystal data

  • C16H23NO4
  • M r = 293.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1754-efi1.jpg
  • a = 9.4350 (19) Å
  • b = 9.1640 (18) Å
  • c = 20.166 (4) Å
  • β = 94.67 (3)°
  • V = 1737.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.12 × 0.10 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.991, T max = 0.994
  • 8863 measured reflections
  • 3169 independent reflections
  • 1612 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.221
  • S = 1.04
  • 3169 reflections
  • 196 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024696/bi2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024696/bi2379Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Science Foundation of Maoming University.

supplementary crystallographic information

Comment

As a part of our ongoing research on the synthesis and structure of Schiff-base ligands based on 5-aminoisophthalic acid, we obtained the title compound from acid-catalysed esterification in 1-butanol.

Experimental

5-Aminoisophthalic acid (10 g) was refluxed overnight in 1-butanol with catalysis of concentrated H2SO4. The solution was poured onto ice and adjusted to pH = 7, and the obtained powder was recrystallized from ethanol. Elemental analysis calculated: C 65.45, H 7.84, N 4.77%; found: C 65.42, H 7.81, N 4.70%.

Refinement

All H atoms bound to C atoms were geometrically positioned and refined using a riding model, with C—H = 0.93 (aryl), 0.97 (methylene) or 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, methylene) or 1.5Ueq(C) (methyl). H atoms on amino N were located from difference Fourier maps and their positions were refined freely, with Uiso(H) = 1.5Ueq(N). The refined N—H distances are 0.83 (5) and 0.83 (6) Å.

Figures

Fig. 1.
Molecular structure with 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
One-dimensional hydrogen-bonded motif.

Crystal data

C16H23NO4F(000) = 632
Mr = 293.35Dx = 1.121 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3119 reflections
a = 9.4350 (19) Åθ = 2.0–25.5°
b = 9.1640 (18) ŵ = 0.08 mm1
c = 20.166 (4) ÅT = 296 K
β = 94.67 (3)°Block, colourless
V = 1737.8 (6) Å30.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer3169 independent reflections
Radiation source: fine-focus sealed tube1612 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −7→11
Tmin = 0.991, Tmax = 0.994k = −11→10
8863 measured reflectionsl = −24→23

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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.1119P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
3169 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
O10.8685 (2)0.3309 (2)0.44186 (12)0.1051 (8)
O20.6509 (2)0.3015 (2)0.39278 (11)0.0938 (7)
O30.3317 (2)0.8767 (3)0.44890 (13)0.1092 (8)
O40.29283 (19)0.6651 (2)0.39827 (11)0.0944 (7)
N10.8560 (3)0.8512 (4)0.5269 (2)0.1380 (15)
H1A0.933 (6)0.815 (7)0.540 (3)0.207*
H1B0.831 (6)0.926 (6)0.546 (3)0.207*
C10.7518 (3)0.3783 (3)0.42708 (14)0.0759 (8)
C20.7015 (2)0.5250 (3)0.44442 (12)0.0674 (7)
C30.7986 (3)0.6180 (3)0.47724 (14)0.0768 (8)
H3A0.89170.58680.48720.092*
C40.7598 (3)0.7572 (3)0.49558 (15)0.0856 (9)
C50.6193 (3)0.8002 (3)0.47979 (15)0.0808 (8)
H5A0.59050.89280.49190.097*
C60.5223 (3)0.7080 (3)0.44666 (13)0.0681 (7)
C70.5629 (3)0.5693 (3)0.42860 (12)0.0675 (7)
H7A0.49770.50680.40620.081*
C80.3749 (3)0.7609 (3)0.43193 (15)0.0784 (8)
C90.1463 (3)0.7056 (4)0.38233 (19)0.1024 (10)
H9A0.14060.79010.35330.123*
H9B0.10170.72960.42260.123*
C100.0741 (4)0.5806 (5)0.3489 (3)0.1371 (16)
H10A0.06570.50540.38220.165*
H10B−0.02180.61150.33440.165*
C110.1293 (6)0.5169 (9)0.2960 (4)0.220 (3)
H11A0.22570.48700.31010.265*
H11B0.13580.59120.26210.265*
C120.0559 (7)0.3906 (9)0.2644 (5)0.300 (6)
H12A0.10460.36020.22670.450*
H12B−0.04010.41700.24990.450*
H12C0.05530.31190.29580.450*
C130.6881 (4)0.1552 (3)0.3734 (2)0.1112 (11)
H13A0.72340.09920.41210.133*
H13B0.76140.15840.34240.133*
C140.5572 (5)0.0874 (4)0.3415 (3)0.1471 (16)
H14A0.5822−0.01000.32770.177*
H14B0.49130.07620.37570.177*
C150.4815 (6)0.1559 (6)0.2858 (3)0.175 (2)
H15A0.54470.16390.25040.210*
H15B0.45700.25420.29860.210*
C160.3471 (6)0.0794 (7)0.2586 (3)0.205 (3)
H16A0.30440.13310.22120.307*
H16B0.28170.07400.29260.307*
H16C0.3698−0.01730.24470.307*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0690 (13)0.0819 (14)0.160 (2)0.0183 (10)−0.0158 (13)−0.0206 (13)
O20.0795 (13)0.0724 (13)0.1264 (16)0.0090 (10)−0.0112 (11)−0.0208 (11)
O30.0665 (12)0.0882 (15)0.169 (2)0.0181 (11)−0.0143 (12)−0.0307 (14)
O40.0608 (11)0.0900 (14)0.1280 (17)0.0102 (10)−0.0193 (10)−0.0165 (12)
N10.0748 (18)0.093 (2)0.237 (4)0.0125 (15)−0.046 (2)−0.060 (2)
C10.0668 (17)0.0684 (17)0.0917 (19)0.0034 (14)0.0007 (14)−0.0048 (14)
C20.0591 (14)0.0654 (15)0.0775 (16)0.0036 (12)0.0031 (12)0.0013 (12)
C30.0570 (14)0.0715 (18)0.0993 (19)0.0082 (12)−0.0090 (13)−0.0062 (14)
C40.0631 (16)0.0731 (19)0.117 (2)0.0039 (14)−0.0137 (15)−0.0129 (16)
C50.0621 (16)0.0667 (16)0.111 (2)0.0084 (13)−0.0059 (14)−0.0116 (15)
C60.0563 (14)0.0651 (16)0.0821 (17)0.0020 (12)−0.0004 (12)0.0021 (13)
C70.0604 (15)0.0667 (16)0.0747 (16)0.0012 (12)0.0006 (12)0.0007 (12)
C80.0611 (15)0.0721 (19)0.100 (2)0.0036 (14)−0.0054 (14)−0.0018 (15)
C90.0600 (17)0.119 (3)0.123 (2)0.0091 (17)−0.0191 (16)−0.007 (2)
C100.080 (2)0.156 (4)0.168 (4)0.000 (2)−0.030 (2)−0.036 (3)
C110.127 (4)0.280 (8)0.248 (7)−0.001 (5)−0.022 (4)−0.138 (7)
C120.173 (6)0.301 (10)0.410 (13)−0.007 (5)−0.074 (6)−0.230 (10)
C130.114 (3)0.073 (2)0.143 (3)0.0126 (18)−0.009 (2)−0.0249 (19)
C140.155 (4)0.088 (3)0.190 (4)0.007 (2)−0.038 (3)−0.042 (3)
C150.168 (4)0.148 (4)0.197 (5)0.010 (3)−0.052 (4)−0.041 (4)
C160.140 (4)0.228 (6)0.235 (6)−0.002 (4)−0.053 (4)−0.094 (5)

Geometric parameters (Å, °)

O1—C11.198 (3)C9—H9B0.970
O2—C11.331 (3)C10—C111.357 (6)
O2—C131.448 (4)C10—H10A0.970
O3—C81.197 (3)C10—H10B0.970
O4—C81.321 (3)C11—C121.468 (8)
O4—C91.442 (3)C11—H11A0.970
N1—C41.368 (4)C11—H11B0.970
N1—H1A0.83 (5)C12—H12A0.960
N1—H1B0.83 (6)C12—H12B0.960
C1—C21.478 (4)C12—H12C0.960
C2—C31.380 (4)C13—C141.481 (5)
C2—C71.382 (3)C13—H13A0.970
C3—C41.385 (4)C13—H13B0.970
C3—H3A0.930C14—C151.426 (7)
C4—C51.395 (4)C14—H14A0.970
C5—C61.377 (4)C14—H14B0.970
C5—H5A0.930C15—C161.513 (7)
C6—C71.385 (3)C15—H15A0.970
C6—C81.480 (4)C15—H15B0.970
C7—H7A0.930C16—H16A0.960
C9—C101.468 (5)C16—H16B0.960
C9—H9A0.970C16—H16C0.960
C1—O2—C13116.8 (2)C9—C10—H10B107.3
C8—O4—C9117.0 (2)H10A—C10—H10B106.9
C4—N1—H1A116 (4)C10—C11—C12118.9 (7)
C4—N1—H1B122 (4)C10—C11—H11A107.6
H1A—N1—H1B117 (5)C12—C11—H11A107.6
O1—C1—O2122.8 (2)C10—C11—H11B107.6
O1—C1—C2125.3 (3)C12—C11—H11B107.6
O2—C1—C2112.0 (2)H11A—C11—H11B107.0
C3—C2—C7120.6 (2)C11—C12—H12A109.5
C3—C2—C1117.5 (2)C11—C12—H12B109.5
C7—C2—C1121.9 (2)H12A—C12—H12B109.5
C2—C3—C4121.1 (2)C11—C12—H12C109.5
C2—C3—H3A119.4H12A—C12—H12C109.5
C4—C3—H3A119.4H12B—C12—H12C109.5
N1—C4—C3121.5 (2)O2—C13—C14107.1 (3)
N1—C4—C5120.7 (3)O2—C13—H13A110.3
C3—C4—C5117.8 (2)C14—C13—H13A110.3
C6—C5—C4121.3 (3)O2—C13—H13B110.3
C6—C5—H5A119.4C14—C13—H13B110.3
C4—C5—H5A119.4H13A—C13—H13B108.6
C5—C6—C7120.2 (2)C15—C14—C13120.2 (5)
C5—C6—C8118.2 (2)C15—C14—H14A107.3
C7—C6—C8121.5 (2)C13—C14—H14A107.3
C2—C7—C6119.0 (2)C15—C14—H14B107.3
C2—C7—H7A120.5C13—C14—H14B107.3
C6—C7—H7A120.5H14A—C14—H14B106.9
O3—C8—O4122.5 (2)C14—C15—C16115.7 (5)
O3—C8—C6124.7 (3)C14—C15—H15A108.4
O4—C8—C6112.8 (3)C16—C15—H15A108.4
O4—C9—C10107.6 (3)C14—C15—H15B108.4
O4—C9—H9A110.2C16—C15—H15B108.4
C10—C9—H9A110.2H15A—C15—H15B107.4
O4—C9—H9B110.2C15—C16—H16A109.5
C10—C9—H9B110.2C15—C16—H16B109.5
H9A—C9—H9B108.5H16A—C16—H16B109.5
C11—C10—C9120.2 (4)C15—C16—H16C109.5
C11—C10—H10A107.3H16A—C16—H16C109.5
C9—C10—H10A107.3H16B—C16—H16C109.5
C11—C10—H10B107.3
C13—O2—C1—O1−0.1 (5)C1—C2—C7—C6179.6 (2)
C13—O2—C1—C2−179.6 (3)C5—C6—C7—C20.1 (4)
O1—C1—C2—C33.6 (4)C8—C6—C7—C2−179.1 (2)
O2—C1—C2—C3−176.9 (2)C9—O4—C8—O30.0 (4)
O1—C1—C2—C7−176.5 (3)C9—O4—C8—C6179.1 (2)
O2—C1—C2—C73.0 (4)C5—C6—C8—O3−2.9 (5)
C7—C2—C3—C40.5 (4)C7—C6—C8—O3176.4 (3)
C1—C2—C3—C4−179.6 (3)C5—C6—C8—O4178.0 (2)
C2—C3—C4—N1−178.7 (3)C7—C6—C8—O4−2.7 (4)
C2—C3—C4—C50.0 (4)C8—O4—C9—C10−176.6 (3)
N1—C4—C5—C6178.2 (3)O4—C9—C10—C11−51.7 (6)
C3—C4—C5—C6−0.4 (5)C9—C10—C11—C12179.0 (7)
C4—C5—C6—C70.4 (4)C1—O2—C13—C14175.1 (3)
C4—C5—C6—C8179.6 (3)O2—C13—C14—C1556.2 (6)
C3—C2—C7—C6−0.5 (4)C13—C14—C15—C16−178.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.83 (5)2.30 (6)3.110 (4)165 (6)
N1—H1B···O3ii0.83 (6)2.38 (6)3.120 (4)149 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2379).

References

  • Bruker (2001). SADABS and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dobson, A. J. & Gerkin, R. E. (1998). Acta Cryst. C54, 1503–1505. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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