Literature DB >> 21523071

N,N'-Bis(4-amino-benz-yl)oxalamide.

Juan Saulo Gonzalez-Gonzalez, Francisco J Martínez-Martínez, Efrén V García-Báez, Olivia M Franco-Hernández, Itzia I Padilla-Martínez.   

Abstract

In the title compound, C(16)H(18)N(4)O(2), the two carbonyl groups are in an anti-periplanar conformation with an O=C-C=O torsion angle of 173.86 (17)°. In the crystal, a pair of inter-molecular N-H⋯O hydrogen bonds, forming an R(2) (2)(10) ring motif, connect the mol-ecules into an inversion dimer. The dimers are further linked by N-H⋯N and C-H⋯π inter-actions, forming a zigzag chain along the b axis.

Entities:  

Year:  2011        PMID： 21523071      PMCID： PMC3051624          DOI： 10.1107/S1600536811000882

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Lee & Wang (2007 ▶). For background to and applications of oxalamides, see: Martínez-Martínez et al. (1998 ▶); Padilla-Martínez et al. (2001 ▶); Nguyen et al. (2001 ▶).

Experimental

Crystal data

C16H18N4O2 M = 298.34 Monoclinic, a = 10.7970 (9) Å b = 8.0930 (8) Å c = 17.9888 (7) Å β = 110.151 (10)° V = 1475.7 (2) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer 13460 measured reflections 2577 independent reflections 2041 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.141 S = 1.05 2577 reflections 199 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000882/is2647sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000882/is2647Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H18N4O2F(000) = 632
Mr = 298.34Dx = 1.343 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 600 reflections
a = 10.7970 (9) Åθ = 20–25°
b = 8.0930 (8) ŵ = 0.09 mm−1
c = 17.9888 (7) ÅT = 293 K
β = 110.151 (10)°Prism, colorless
V = 1475.7 (2) Å30.40 × 0.30 × 0.20 mm
Z = 4
Bruker APEXII area-detector diffractometer2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
graphiteθmax = 25.0°, θmin = 2.4°
φ and ω scansh = −12→12
13460 measured reflectionsk = −8→9
2577 independent reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0744P)2 + 0.3652P] where P = (Fo2 + 2Fc2)/3
2577 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > σ(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.
xyzUiso*/Ueq
O9−0.04287 (12)0.80255 (17)0.03285 (8)0.0510 (4)
O100.28644 (13)0.6703 (2)0.11061 (9)0.0636 (5)
N4−0.22384 (17)0.7608 (2)0.35278 (10)0.0581 (6)
N80.04232 (14)0.56568 (19)0.09827 (9)0.0439 (5)
N110.19920 (15)0.8886 (2)0.03145 (9)0.0478 (5)
N160.4741 (2)0.6082 (3)−0.21045 (14)0.0872 (9)
C1−0.12077 (16)0.5601 (2)0.16642 (10)0.0404 (6)
C2−0.22418 (18)0.6700 (3)0.15269 (11)0.0488 (6)
C3−0.26137 (18)0.7320 (3)0.21331 (11)0.0505 (7)
C4−0.19297 (17)0.6871 (2)0.29106 (11)0.0431 (6)
C5−0.09016 (19)0.5751 (3)0.30558 (11)0.0493 (6)
C6−0.05570 (18)0.5125 (3)0.24415 (11)0.0488 (6)
C7−0.08159 (18)0.4955 (3)0.09935 (11)0.0472 (6)
C90.05074 (17)0.7099 (2)0.06609 (10)0.0399 (6)
C100.19201 (18)0.7547 (2)0.07215 (10)0.0430 (6)
C120.3227 (2)0.9461 (3)0.02409 (13)0.0561 (7)
C130.36006 (17)0.8540 (2)−0.03788 (11)0.0453 (6)
C140.45884 (18)0.7383 (3)−0.01763 (13)0.0542 (7)
C150.4959 (2)0.6559 (3)−0.07410 (15)0.0610 (8)
C160.4330 (2)0.6865 (3)−0.15412 (13)0.0563 (7)
C170.3328 (2)0.8023 (3)−0.17473 (13)0.0667 (8)
C180.2968 (2)0.8838 (3)−0.11778 (13)0.0600 (7)
H2−0.270130.703230.101010.0586*
H3−0.332540.804160.201980.0606*
H4A−0.285230.833930.342510.0696*
H4B−0.181440.732960.401020.0696*
H5−0.044050.541850.357240.0591*
H60.012870.436450.255130.0586*
H7A−0.150960.520590.049620.0567*
H7B−0.073000.376230.103760.0567*
H80.113640.510100.119730.0527*
H110.128280.943900.008440.0574*
H12A0.314591.062730.010870.0673*
H12B0.392910.933920.074830.0673*
H14A0.502240.714380.035610.0650*
H150.563890.57895−0.058110.0732*
H16A0.436920.63146−0.259820.1046*
H16B0.536770.53665−0.195910.1046*
H170.288770.82581−0.227940.0801*
H180.228430.96034−0.133530.0720*
U11U22U33U12U13U23
O90.0456 (7)0.0494 (8)0.0576 (8)0.0014 (6)0.0173 (6)0.0056 (6)
O100.0457 (8)0.0741 (10)0.0721 (10)0.0067 (7)0.0219 (7)0.0212 (8)
N40.0659 (11)0.0607 (11)0.0553 (10)0.0091 (9)0.0308 (9)−0.0015 (8)
N80.0436 (8)0.0456 (9)0.0468 (9)0.0005 (7)0.0212 (7)0.0029 (7)
N110.0457 (9)0.0467 (9)0.0575 (9)−0.0019 (7)0.0261 (7)0.0031 (8)
N160.0781 (13)0.1039 (18)0.1004 (16)−0.0224 (13)0.0575 (12)−0.0310 (14)
C10.0394 (9)0.0395 (10)0.0437 (10)−0.0073 (7)0.0163 (8)−0.0001 (8)
C20.0422 (10)0.0619 (13)0.0405 (10)0.0012 (9)0.0119 (8)0.0086 (9)
C30.0406 (10)0.0573 (12)0.0553 (12)0.0093 (9)0.0187 (9)0.0087 (10)
C40.0428 (10)0.0425 (10)0.0489 (10)−0.0055 (8)0.0220 (8)0.0014 (8)
C50.0525 (11)0.0547 (12)0.0403 (10)0.0066 (9)0.0156 (8)0.0079 (9)
C60.0480 (10)0.0468 (11)0.0526 (11)0.0088 (9)0.0186 (9)0.0036 (9)
C70.0497 (10)0.0462 (11)0.0500 (11)−0.0096 (9)0.0226 (9)−0.0050 (9)
C90.0432 (10)0.0431 (10)0.0362 (9)−0.0010 (8)0.0173 (8)−0.0044 (8)
C100.0442 (10)0.0477 (11)0.0399 (9)−0.0013 (9)0.0179 (8)−0.0017 (8)
C120.0536 (12)0.0529 (12)0.0691 (13)−0.0151 (9)0.0305 (10)−0.0055 (10)
C130.0384 (9)0.0474 (11)0.0541 (11)−0.0074 (8)0.0210 (8)0.0058 (9)
C140.0426 (10)0.0638 (13)0.0574 (12)−0.0010 (10)0.0187 (9)0.0143 (10)
C150.0513 (12)0.0529 (13)0.0876 (16)0.0037 (10)0.0351 (11)0.0096 (12)
C160.0477 (11)0.0610 (13)0.0701 (14)−0.0178 (10)0.0329 (10)−0.0091 (11)
C170.0548 (12)0.0921 (18)0.0524 (12)−0.0055 (12)0.0174 (10)0.0059 (12)
C180.0485 (11)0.0689 (14)0.0639 (13)0.0098 (10)0.0210 (10)0.0134 (11)
O9—C91.235 (2)C9—C101.535 (3)
O10—C101.224 (2)C12—C131.507 (3)
N4—C41.398 (3)C13—C181.384 (3)
N8—C71.460 (3)C13—C141.371 (3)
N8—C91.320 (2)C14—C151.385 (3)
N11—C101.325 (2)C15—C161.386 (3)
N11—C121.461 (3)C16—C171.382 (3)
N16—C161.391 (3)C17—C181.382 (3)
N4—H4A0.8600C2—H20.9300
N4—H4B0.8600C3—H30.9300
N8—H80.8600C5—H50.9300
N11—H110.8600C6—H60.9300
N16—H16A0.8600C7—H7A0.9700
N16—H16B0.8600C7—H7B0.9700
C1—C61.386 (3)C12—H12A0.9700
C1—C71.503 (3)C12—H12B0.9700
C1—C21.382 (3)C14—H14A0.9300
C2—C31.380 (3)C15—H150.9300
C3—C41.386 (3)C17—H170.9300
C4—C51.386 (3)C18—H180.9300
C5—C61.378 (3)
O9···N112.713 (2)H2···C14xi2.9800
O9···N11i3.015 (2)H2···H7A2.3500
O9···N4ii3.196 (2)H2···H14Axi2.3300
O10···C133.382 (2)H3···H4A2.4100
O10···N82.704 (2)H3···C18i3.0400
O9···H11i2.2700H4A···H32.4100
O9···H5iii2.6900H4A···O10iii2.8500
O9···H4Bii2.3500H4A···H8iii2.2500
O9···H7A2.6300H4A···N16vii2.4800
O9···H112.3400H4A···C16vii3.0700
O10···H82.3200H4A···H16Bvii2.0900
O10···H12B2.6100H4B···H52.4500
O10···H4Aiv2.8500H4B···H8iii2.4300
O10···H16Bv2.6000H4B···O9vi2.3500
O10···H16Avi2.8300H5···H4B2.4500
O10···H17vi2.9000H5···O9iv2.6900
N4···N8iii3.085 (2)H5···C9iv3.0300
N4···O9vi3.196 (2)H6···C3iv3.0300
N4···N16vii3.240 (3)H7A···O92.6300
N8···O102.704 (2)H7A···H22.3500
N8···N4iv3.085 (2)H7A···C10ix3.0500
N11···O9i3.015 (2)H8···O102.3200
N11···O92.713 (2)H8···N4iv2.3100
N16···N4viii3.240 (3)H8···C4iv3.0300
N4···H16Bvii2.9300H8···H4Aiv2.2500
N4···H8iii2.3100H8···H4Biv2.4300
N16···H4Aviii2.4800H11···O92.3400
C3···C18i3.509 (3)H11···O9i2.2700
C7···C10ix3.536 (3)H12A···H182.5800
C7···C9ix3.523 (3)H12A···C14x2.9000
C9···C7ix3.523 (3)H12A···C15x3.0100
C10···C7ix3.536 (3)H12B···O102.6100
C12···C14x3.506 (3)H12B···H14A2.3700
C13···O103.382 (2)H14A···C2xii3.0000
C14···C15v3.547 (3)H14A···H2xii2.3300
C14···C12x3.506 (3)H14A···H12B2.3700
C15···C14v3.547 (3)H14A···C15v3.0700
C18···C3i3.509 (3)H14A···H15v2.5500
C2···H18i3.0100H15···H16B2.4200
C2···H14Axi3.0000H15···C14v2.9600
C3···H18i2.9600H15···H14Av2.5500
C3···H6iii3.0300H16A···H172.4500
C4···H8iii3.0300H16A···O10ii2.8300
C9···H5iii3.0300H16B···H152.4200
C10···H7Aix3.0500H16B···O10v2.6000
C14···H2xii2.9800H16B···N4viii2.9300
C14···H15v2.9600H16B···H4Aviii2.0900
C14···H12Ax2.9000H17···H16A2.4500
C15···H14Av3.0700H17···O10ii2.9000
C15···H12Ax3.0100H18···H12A2.5800
C16···H4Aviii3.0700H18···C2i3.0100
C18···H3i3.0400H18···C3i2.9600
C7—N8—C9123.50 (17)C13—C14—C15121.9 (2)
C10—N11—C12122.67 (17)C14—C15—C16120.9 (2)
H4A—N4—H4B120.00N16—C16—C17122.0 (2)
C4—N4—H4B120.00N16—C16—C15120.7 (2)
C4—N4—H4A120.00C15—C16—C17117.3 (2)
C7—N8—H8118.00C16—C17—C18121.3 (2)
C9—N8—H8118.00C13—C18—C17121.5 (2)
C10—N11—H11119.00C1—C2—H2119.00
C12—N11—H11119.00C3—C2—H2119.00
C16—N16—H16A120.00C2—C3—H3120.00
C16—N16—H16B120.00C4—C3—H3120.00
H16A—N16—H16B120.00C4—C5—H5120.00
C2—C1—C6117.19 (17)C6—C5—H5120.00
C6—C1—C7121.88 (17)C1—C6—H6119.00
C2—C1—C7120.93 (16)C5—C6—H6119.00
C1—C2—C3122.01 (18)N8—C7—H7A109.00
C2—C3—C4120.2 (2)N8—C7—H7B109.00
N4—C4—C5121.58 (17)C1—C7—H7A109.00
C3—C4—C5118.37 (18)C1—C7—H7B109.00
N4—C4—C3119.97 (17)H7A—C7—H7B108.00
C4—C5—C6120.60 (18)N11—C12—H12A109.00
C1—C6—C5121.6 (2)N11—C12—H12B109.00
N8—C7—C1112.83 (17)C13—C12—H12A109.00
O9—C9—N8125.51 (18)C13—C12—H12B109.00
O9—C9—C10121.24 (15)H12A—C12—H12B108.00
N8—C9—C10113.25 (15)C13—C14—H14A119.00
O10—C10—C9121.48 (16)C15—C14—H14A119.00
N11—C10—C9113.58 (16)C14—C15—H15120.00
O10—C10—N11124.94 (19)C16—C15—H15120.00
N11—C12—C13113.26 (18)C16—C17—H17119.00
C12—C13—C18121.34 (18)C18—C17—H17119.00
C12—C13—C14121.55 (18)C13—C18—H18119.00
C14—C13—C18117.10 (19)C17—C18—H18119.00
C7—N8—C9—C10−179.47 (15)C4—C5—C6—C10.8 (3)
C9—N8—C7—C1−83.4 (2)O9—C9—C10—O10173.86 (17)
C7—N8—C9—O9−0.5 (3)O9—C9—C10—N11−7.1 (2)
C12—N11—C10—O103.8 (3)N8—C9—C10—O10−7.1 (2)
C10—N11—C12—C1380.5 (2)N8—C9—C10—N11171.93 (15)
C12—N11—C10—C9−175.23 (16)N11—C12—C13—C14−105.0 (2)
C2—C1—C6—C5−1.6 (3)N11—C12—C13—C1875.6 (2)
C7—C1—C2—C3−179.5 (2)C12—C13—C14—C15−178.5 (2)
C6—C1—C7—N8−72.8 (2)C18—C13—C14—C151.0 (3)
C7—C1—C6—C5178.5 (2)C12—C13—C18—C17178.5 (2)
C6—C1—C2—C30.6 (3)C14—C13—C18—C17−0.9 (3)
C2—C1—C7—N8107.3 (2)C13—C14—C15—C16−0.6 (4)
C1—C2—C3—C41.3 (3)C14—C15—C16—N16177.4 (2)
C2—C3—C4—N4174.6 (2)C14—C15—C16—C170.2 (4)
C2—C3—C4—C5−2.1 (3)N16—C16—C17—C18−177.4 (2)
N4—C4—C5—C6−175.6 (2)C15—C16—C17—C18−0.1 (4)
C3—C4—C5—C61.1 (3)C16—C17—C18—C130.5 (4)
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N4—H4A···N16vii0.862.483.240 (3)147
N4—H4B···O9vi0.862.353.196 (2)170
N8—H8···O100.862.322.704 (2)107
N8—H8···N4iv0.862.313.085 (2)150
N11—H11···O90.862.342.713 (2)107
N11—H11···O9i0.862.273.015 (2)145
C6—H6···Cg1iv0.932.943.836 (3)162
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4—H4A⋯N16i0.862.483.240 (3)147
N4—H4B⋯O9ii0.862.353.196 (2)170
N8—H8⋯N4iii0.862.313.085 (2)150
N11—H11⋯O9iv0.862.273.015 (2)145
C6—H6⋯Cg1iii0.932.943.836 (3)162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

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