N,N′-Bis(4-amino­benz­yl)oxalamide

Gonzalez-Gonzalez, J.S.; Martínez-Martínez, F.J.; García-Báez, E.V.; Franco-Hernández, O.M.; Padilla-Martínez, I.I.

doi:10.1107/S1600536811000882

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o398

doi:10.1107/S1600536811000882

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N,N′-Bis(4-aminobenzyl)oxalamide

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

^aFacultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán-Colima, Coquimatlán Colima, Mexico 28400, and ^bUnidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Avenida Acueducto s/n, Barrio La Laguna Ticomán, México DF 07340, Mexico
^*Correspondence e-mail: fjmartin@ucol.mx

(Received 16 December 2010; accepted 6 January 2011; online 15 January 2011)

In the title compound, C₁₆H₁₈N₄O₂, the two carbonyl groups are in an antiperiplanar conformation with an O=C—C=O torsion angle of 173.86 (17)°. In the crystal, a pair of intermolecular N—H⋯O hydrogen bonds, forming an R₂²(10) ring motif, connect the molecules into an inversion dimer. The dimers are further linked by N—H⋯N and C—H⋯π interactions, forming a zigzag chain along the b axis.

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_r = 298.34
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.141
S = 1.05
2577 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N16ⁱ	0.86	2.48	3.240 (3)	147
N4—H4B⋯O9ⁱⁱ	0.86	2.35	3.196 (2)	170
N8—H8⋯N4ⁱⁱⁱ	0.86	2.31	3.085 (2)	150
N11—H11⋯O9^iv	0.86	2.27	3.015 (2)	145
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.94	3.836 (3)	162
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+2, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000882/is2647sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000882/is2647Isup2.hkl

checkCIF report

Comment top

The chemical structure of oxalamides favors the formation of intra and intermolecular hydrogen bonding interactions (Martínez-Martínez et al., 1998; Padilla-Martínez et al., 2001; Nguyen et al., 2001). Herein we present the title compound, (I), a new bis-oxalamide.

The title compound (I) forms monoclinic crystals (P2₁/c, Z = 4). Carbonyl groups are antiperiplanar, with an O9—C9—C10—O10 torsion angle of 173.86 (17)°. The oxalamide group is almost planar, with an N8—C9—C10—N11 torsion angle of 171.92 (17)°. The aminobenzyl groups are twisted by 69.43 (5)° (C1—C7/N4) and 73.78 (5)° (C13—C18/N16) out of the oxalamide group mean plane (C7/N8/C9/O9/C10/O10/N11/C12) and are almost parallel to each other with an angle between the planes of 4.56 (5)°. According to graph-set notation (Bernstein et al., 1995), two S(5) rings are formed through N8—H8···O10 and N11—H11···O9 interactions. N···O distances and N—H···O angles are in the range for strong hydrogen bonding, in agreement with similar structures (Lee and Wang, 2007). The zero dimensional array is given by pairing of two molecules through self complementary strong N11—H11···O9 hydrogen bonding, to form the R²₂(10) motif characteristic of oxalamides. The molecules are connected by N8—H8···N4 and C6—H6···Cg1 into a zigzag chain running along the b axis; Cg1 is the centroid of the C1–C6 ring. Amine N4—H4A···N16 and N4—H4B···O9 hydrogen bonding interactions give the second and third dimensions, forming C(17) and C(10) chains, respectively.

Related literature top

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 top

A mixture of diethyl oxalate (2 ml,14 mmol) and 4-aminobenzylamine (3.34 ml, 28 mmol) in ethanol (30 ml) was refluxed for 6 h. The suspension was filtered and the resulting solid was washed with cold ethyl alcohol to yield 3.25 g (73%) of a pale yellow solid (m.p. 250–252 °C).

IR (neat, cm^-1): 3415, 3346, 3202, 3038, 1651. Anal. calcd. for C₁₆H₁₈N₄O₂: C 64.41, H 6.08, N 18.78%; found: C 64.07, H 6.25, N 18.44%. ¹H NMR (300 MHz, DMSO_d-6, δ) CH₂ 4.11 (d, 2H), NH 9.03 (t, 1H), Aromatics: 6.46 (d, 2H), 6.90 (d, 2H), NH₂ 4.95 (s, 2H). ¹³C NMR (75.46 MHz, DMSO_d-6, δ) 42.7, 114.2, 126.3, 129.1, 148.3, 160.5. ESI MS = calc. m/z 298.14, found m/z 320.8 [M + Na]⁺.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed lines indicate intramolecular hydrogen bonding.
	Fig. 2. Packing diagram of the title compound, dashed lines indicate intermolecular hydrogen bonding.

N,N'-Bis(4-aminobenzyl)oxalamide top

Crystal data top

C₁₆H₁₈N₄O₂	F(000) = 632
M_r = 298.34	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 10.7970 (9) Å	θ = 20–25°
b = 8.0930 (8) Å	µ = 0.09 mm⁻¹
c = 17.9888 (7) Å	T = 293 K
β = 110.151 (10)°	Prism, colorless
V = 1475.7 (2) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
ϕ and ω scans	h = −12→12
13460 measured reflections	k = −8→9
2577 independent reflections	l = −21→21

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0744P)² + 0.3652P] where P = (F_o² + 2F_c²)/3
2577 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₈N₄O₂	V = 1475.7 (2) Å³
M_r = 298.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7970 (9) Å	µ = 0.09 mm⁻¹
b = 8.0930 (8) Å	T = 293 K
c = 17.9888 (7) Å	0.40 × 0.30 × 0.20 mm
β = 110.151 (10)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
2577 reflections	Δρ_min = −0.21 e Å⁻³
199 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O9	−0.04287 (12)	0.80255 (17)	0.03285 (8)	0.0510 (4)
O10	0.28644 (13)	0.6703 (2)	0.11061 (9)	0.0636 (5)
N4	−0.22384 (17)	0.7608 (2)	0.35278 (10)	0.0581 (6)
N8	0.04232 (14)	0.56568 (19)	0.09827 (9)	0.0439 (5)
N11	0.19920 (15)	0.8886 (2)	0.03145 (9)	0.0478 (5)
N16	0.4741 (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)
C9	0.05074 (17)	0.7099 (2)	0.06609 (10)	0.0399 (6)
C10	0.19201 (18)	0.7547 (2)	0.07215 (10)	0.0430 (6)
C12	0.3227 (2)	0.9461 (3)	0.02409 (13)	0.0561 (7)
C13	0.36006 (17)	0.8540 (2)	−0.03788 (11)	0.0453 (6)
C14	0.45884 (18)	0.7383 (3)	−0.01763 (13)	0.0542 (7)
C15	0.4959 (2)	0.6559 (3)	−0.07410 (15)	0.0610 (8)
C16	0.4330 (2)	0.6865 (3)	−0.15412 (13)	0.0563 (7)
C17	0.3328 (2)	0.8023 (3)	−0.17473 (13)	0.0667 (8)
C18	0.2968 (2)	0.8838 (3)	−0.11778 (13)	0.0600 (7)
H2	−0.27013	0.70323	0.10101	0.0586*
H3	−0.33254	0.80416	0.20198	0.0606*
H4A	−0.28523	0.83393	0.34251	0.0696*
H4B	−0.18144	0.73296	0.40102	0.0696*
H5	−0.04405	0.54185	0.35724	0.0591*
H6	0.01287	0.43645	0.25513	0.0586*
H7A	−0.15096	0.52059	0.04962	0.0567*
H7B	−0.07300	0.37623	0.10376	0.0567*
H8	0.11364	0.51010	0.11973	0.0527*
H11	0.12828	0.94390	0.00844	0.0574*
H12A	0.31459	1.06273	0.01087	0.0673*
H12B	0.39291	0.93392	0.07483	0.0673*
H14A	0.50224	0.71438	0.03561	0.0650*
H15	0.56389	0.57895	−0.05811	0.0732*
H16A	0.43692	0.63146	−0.25982	0.1046*
H16B	0.53677	0.53665	−0.19591	0.1046*
H17	0.28877	0.82581	−0.22794	0.0801*
H18	0.22843	0.96034	−0.13353	0.0720*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O9	0.0456 (7)	0.0494 (8)	0.0576 (8)	0.0014 (6)	0.0173 (6)	0.0056 (6)
O10	0.0457 (8)	0.0741 (10)	0.0721 (10)	0.0067 (7)	0.0219 (7)	0.0212 (8)
N4	0.0659 (11)	0.0607 (11)	0.0553 (10)	0.0091 (9)	0.0308 (9)	−0.0015 (8)
N8	0.0436 (8)	0.0456 (9)	0.0468 (9)	0.0005 (7)	0.0212 (7)	0.0029 (7)
N11	0.0457 (9)	0.0467 (9)	0.0575 (9)	−0.0019 (7)	0.0261 (7)	0.0031 (8)
N16	0.0781 (13)	0.1039 (18)	0.1004 (16)	−0.0224 (13)	0.0575 (12)	−0.0310 (14)
C1	0.0394 (9)	0.0395 (10)	0.0437 (10)	−0.0073 (7)	0.0163 (8)	−0.0001 (8)
C2	0.0422 (10)	0.0619 (13)	0.0405 (10)	0.0012 (9)	0.0119 (8)	0.0086 (9)
C3	0.0406 (10)	0.0573 (12)	0.0553 (12)	0.0093 (9)	0.0187 (9)	0.0087 (10)
C4	0.0428 (10)	0.0425 (10)	0.0489 (10)	−0.0055 (8)	0.0220 (8)	0.0014 (8)
C5	0.0525 (11)	0.0547 (12)	0.0403 (10)	0.0066 (9)	0.0156 (8)	0.0079 (9)
C6	0.0480 (10)	0.0468 (11)	0.0526 (11)	0.0088 (9)	0.0186 (9)	0.0036 (9)
C7	0.0497 (10)	0.0462 (11)	0.0500 (11)	−0.0096 (9)	0.0226 (9)	−0.0050 (9)
C9	0.0432 (10)	0.0431 (10)	0.0362 (9)	−0.0010 (8)	0.0173 (8)	−0.0044 (8)
C10	0.0442 (10)	0.0477 (11)	0.0399 (9)	−0.0013 (9)	0.0179 (8)	−0.0017 (8)
C12	0.0536 (12)	0.0529 (12)	0.0691 (13)	−0.0151 (9)	0.0305 (10)	−0.0055 (10)
C13	0.0384 (9)	0.0474 (11)	0.0541 (11)	−0.0074 (8)	0.0210 (8)	0.0058 (9)
C14	0.0426 (10)	0.0638 (13)	0.0574 (12)	−0.0010 (10)	0.0187 (9)	0.0143 (10)
C15	0.0513 (12)	0.0529 (13)	0.0876 (16)	0.0037 (10)	0.0351 (11)	0.0096 (12)
C16	0.0477 (11)	0.0610 (13)	0.0701 (14)	−0.0178 (10)	0.0329 (10)	−0.0091 (11)
C17	0.0548 (12)	0.0921 (18)	0.0524 (12)	−0.0055 (12)	0.0174 (10)	0.0059 (12)
C18	0.0485 (11)	0.0689 (14)	0.0639 (13)	0.0098 (10)	0.0210 (10)	0.0134 (11)

Geometric parameters (Å, º) top

O9—C9	1.235 (2)	C9—C10	1.535 (3)
O10—C10	1.224 (2)	C12—C13	1.507 (3)
N4—C4	1.398 (3)	C13—C18	1.384 (3)
N8—C7	1.460 (3)	C13—C14	1.371 (3)
N8—C9	1.320 (2)	C14—C15	1.385 (3)
N11—C10	1.325 (2)	C15—C16	1.386 (3)
N11—C12	1.461 (3)	C16—C17	1.382 (3)
N16—C16	1.391 (3)	C17—C18	1.382 (3)
N4—H4A	0.8600	C2—H2	0.9300
N4—H4B	0.8600	C3—H3	0.9300
N8—H8	0.8600	C5—H5	0.9300
N11—H11	0.8600	C6—H6	0.9300
N16—H16A	0.8600	C7—H7A	0.9700
N16—H16B	0.8600	C7—H7B	0.9700
C1—C6	1.386 (3)	C12—H12A	0.9700
C1—C7	1.503 (3)	C12—H12B	0.9700
C1—C2	1.382 (3)	C14—H14A	0.9300
C2—C3	1.380 (3)	C15—H15	0.9300
C3—C4	1.386 (3)	C17—H17	0.9300
C4—C5	1.386 (3)	C18—H18	0.9300
C5—C6	1.378 (3)

O9···N11	2.713 (2)	H2···C14^xi	2.9800
O9···N11ⁱ	3.015 (2)	H2···H7A	2.3500
O9···N4ⁱⁱ	3.196 (2)	H2···H14A^xi	2.3300
O10···C13	3.382 (2)	H3···H4A	2.4100
O10···N8	2.704 (2)	H3···C18ⁱ	3.0400
O9···H11ⁱ	2.2700	H4A···H3	2.4100
O9···H5ⁱⁱⁱ	2.6900	H4A···O10ⁱⁱⁱ	2.8500
O9···H4Bⁱⁱ	2.3500	H4A···H8ⁱⁱⁱ	2.2500
O9···H7A	2.6300	H4A···N16^vii	2.4800
O9···H11	2.3400	H4A···C16^vii	3.0700
O10···H8	2.3200	H4A···H16B^vii	2.0900
O10···H12B	2.6100	H4B···H5	2.4500
O10···H4A^iv	2.8500	H4B···H8ⁱⁱⁱ	2.4300
O10···H16B^v	2.6000	H4B···O9^vi	2.3500
O10···H16A^vi	2.8300	H5···H4B	2.4500
O10···H17^vi	2.9000	H5···O9^iv	2.6900
N4···N8ⁱⁱⁱ	3.085 (2)	H5···C9^iv	3.0300
N4···O9^vi	3.196 (2)	H6···C3^iv	3.0300
N4···N16^vii	3.240 (3)	H7A···O9	2.6300
N8···O10	2.704 (2)	H7A···H2	2.3500
N8···N4^iv	3.085 (2)	H7A···C10^ix	3.0500
N11···O9ⁱ	3.015 (2)	H8···O10	2.3200
N11···O9	2.713 (2)	H8···N4^iv	2.3100
N16···N4^viii	3.240 (3)	H8···C4^iv	3.0300
N4···H16B^vii	2.9300	H8···H4A^iv	2.2500
N4···H8ⁱⁱⁱ	2.3100	H8···H4B^iv	2.4300
N16···H4A^viii	2.4800	H11···O9	2.3400
C3···C18ⁱ	3.509 (3)	H11···O9ⁱ	2.2700
C7···C10^ix	3.536 (3)	H12A···H18	2.5800
C7···C9^ix	3.523 (3)	H12A···C14^x	2.9000
C9···C7^ix	3.523 (3)	H12A···C15^x	3.0100
C10···C7^ix	3.536 (3)	H12B···O10	2.6100
C12···C14^x	3.506 (3)	H12B···H14A	2.3700
C13···O10	3.382 (2)	H14A···C2^xii	3.0000
C14···C15^v	3.547 (3)	H14A···H2^xii	2.3300
C14···C12^x	3.506 (3)	H14A···H12B	2.3700
C15···C14^v	3.547 (3)	H14A···C15^v	3.0700
C18···C3ⁱ	3.509 (3)	H14A···H15^v	2.5500
C2···H18ⁱ	3.0100	H15···H16B	2.4200
C2···H14A^xi	3.0000	H15···C14^v	2.9600
C3···H18ⁱ	2.9600	H15···H14A^v	2.5500
C3···H6ⁱⁱⁱ	3.0300	H16A···H17	2.4500
C4···H8ⁱⁱⁱ	3.0300	H16A···O10ⁱⁱ	2.8300
C9···H5ⁱⁱⁱ	3.0300	H16B···H15	2.4200
C10···H7A^ix	3.0500	H16B···O10^v	2.6000
C14···H2^xii	2.9800	H16B···N4^viii	2.9300
C14···H15^v	2.9600	H16B···H4A^viii	2.0900
C14···H12A^x	2.9000	H17···H16A	2.4500
C15···H14A^v	3.0700	H17···O10ⁱⁱ	2.9000
C15···H12A^x	3.0100	H18···H12A	2.5800
C16···H4A^viii	3.0700	H18···C2ⁱ	3.0100
C18···H3ⁱ	3.0400	H18···C3ⁱ	2.9600

C7—N8—C9	123.50 (17)	C13—C14—C15	121.9 (2)
C10—N11—C12	122.67 (17)	C14—C15—C16	120.9 (2)
H4A—N4—H4B	120.00	N16—C16—C17	122.0 (2)
C4—N4—H4B	120.00	N16—C16—C15	120.7 (2)
C4—N4—H4A	120.00	C15—C16—C17	117.3 (2)
C7—N8—H8	118.00	C16—C17—C18	121.3 (2)
C9—N8—H8	118.00	C13—C18—C17	121.5 (2)
C10—N11—H11	119.00	C1—C2—H2	119.00
C12—N11—H11	119.00	C3—C2—H2	119.00
C16—N16—H16A	120.00	C2—C3—H3	120.00
C16—N16—H16B	120.00	C4—C3—H3	120.00
H16A—N16—H16B	120.00	C4—C5—H5	120.00
C2—C1—C6	117.19 (17)	C6—C5—H5	120.00
C6—C1—C7	121.88 (17)	C1—C6—H6	119.00
C2—C1—C7	120.93 (16)	C5—C6—H6	119.00
C1—C2—C3	122.01 (18)	N8—C7—H7A	109.00
C2—C3—C4	120.2 (2)	N8—C7—H7B	109.00
N4—C4—C5	121.58 (17)	C1—C7—H7A	109.00
C3—C4—C5	118.37 (18)	C1—C7—H7B	109.00
N4—C4—C3	119.97 (17)	H7A—C7—H7B	108.00
C4—C5—C6	120.60 (18)	N11—C12—H12A	109.00
C1—C6—C5	121.6 (2)	N11—C12—H12B	109.00
N8—C7—C1	112.83 (17)	C13—C12—H12A	109.00
O9—C9—N8	125.51 (18)	C13—C12—H12B	109.00
O9—C9—C10	121.24 (15)	H12A—C12—H12B	108.00
N8—C9—C10	113.25 (15)	C13—C14—H14A	119.00
O10—C10—C9	121.48 (16)	C15—C14—H14A	119.00
N11—C10—C9	113.58 (16)	C14—C15—H15	120.00
O10—C10—N11	124.94 (19)	C16—C15—H15	120.00
N11—C12—C13	113.26 (18)	C16—C17—H17	119.00
C12—C13—C18	121.34 (18)	C18—C17—H17	119.00
C12—C13—C14	121.55 (18)	C13—C18—H18	119.00
C14—C13—C18	117.10 (19)	C17—C18—H18	119.00

C7—N8—C9—C10	−179.47 (15)	C4—C5—C6—C1	0.8 (3)
C9—N8—C7—C1	−83.4 (2)	O9—C9—C10—O10	173.86 (17)
C7—N8—C9—O9	−0.5 (3)	O9—C9—C10—N11	−7.1 (2)
C12—N11—C10—O10	3.8 (3)	N8—C9—C10—O10	−7.1 (2)
C10—N11—C12—C13	80.5 (2)	N8—C9—C10—N11	171.93 (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—C18	75.6 (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—C15	1.0 (3)
C7—C1—C6—C5	178.5 (2)	C12—C13—C18—C17	178.5 (2)
C6—C1—C2—C3	0.6 (3)	C14—C13—C18—C17	−0.9 (3)
C2—C1—C7—N8	107.3 (2)	C13—C14—C15—C16	−0.6 (4)
C1—C2—C3—C4	1.3 (3)	C14—C15—C16—N16	177.4 (2)
C2—C3—C4—N4	174.6 (2)	C14—C15—C16—C17	0.2 (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—C6	1.1 (3)	C16—C17—C18—C13	0.5 (4)

Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2; (v) −x+1, −y+1, −z; (vi) x, −y+3/2, z+1/2; (vii) x−1, −y+3/2, z+1/2; (viii) x+1, −y+3/2, z−1/2; (ix) −x, −y+1, −z; (x) −x+1, −y+2, −z; (xi) x−1, y, z; (xii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N16^vii	0.86	2.48	3.240 (3)	147
N4—H4B···O9^vi	0.86	2.35	3.196 (2)	170
N8—H8···O10	0.86	2.32	2.704 (2)	107
N8—H8···N4^iv	0.86	2.31	3.085 (2)	150
N11—H11···O9	0.86	2.34	2.713 (2)	107
N11—H11···O9ⁱ	0.86	2.27	3.015 (2)	145
C6—H6···Cg1^iv	0.93	2.94	3.836 (3)	162

Symmetry codes: (i) −x, −y+2, −z; (iv) −x, y−1/2, −z+1/2; (vi) x, −y+3/2, z+1/2; (vii) x−1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₄O₂
M_r	298.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.7970 (9), 8.0930 (8), 17.9888 (7)
β (°)	110.151 (10)
V (Å³)	1475.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13460, 2577, 2041
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.141, 1.05
No. of reflections	2577
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N16ⁱ	0.86	2.48	3.240 (3)	147
N4—H4B···O9ⁱⁱ	0.86	2.35	3.196 (2)	170
N8—H8···O10	0.86	2.32	2.704 (2)	107
N8—H8···N4ⁱⁱⁱ	0.86	2.31	3.085 (2)	150
N11—H11···O9	0.86	2.34	2.713 (2)	107
N11—H11···O9^iv	0.86	2.27	3.015 (2)	145
C6—H6···Cg1ⁱⁱⁱ	0.93	2.94	3.836 (3)	162

Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+2, −z.

Acknowledgements

The authors gratefully acknowledge financial support from the FRABA-Universidad de Colima, CONACYT 83378 and SIP-IPN.

References

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