N′-(4-Bromo­benzyl­idene)quinoline-8-sulfonohydrazide

Oliveira, K.N. de; Nunes, R.J.; Foro, S.

doi:10.1107/S1600536809008848

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o779

doi:10.1107/S1600536809008848

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N′-(4-Bromobenzylidene)quinoline-8-sulfonohydrazide

Kely Navakoski de Oliveira,^a Ricardo José Nunes ^a and Sabine Foro ^b ^*

^aDepartamento de Química–UFSC, 88040-900 Florianópolis, SC, Brazil, and ^bClemens Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, D-64287 Darmstadt, Germany
^*Correspondence e-mail: kely_navakoski@yahoo.com.br

(Received 31 October 2008; accepted 10 March 2009; online 19 March 2009)

In the title compound, C₁₆H₁₂BrN₃O₂S, the dihedral angle between the planes of the almost planar (r.m.s. deviation = 0.0263 Å) quinoline group and the bromophenyl group is 87.4 (1)°. The torsion angle of the central S—N—N—C bridge is 144.8 (2)°. The amino group has an intramolecular contact to the quinoline N atom. The structure is stabilized by one N—H⋯O and two C—H⋯O intermolecular hydrogen bonds.

Related literature

For general background, see: Dueñas-Romero et al. (2006 ); da Silva et al. (2007 ). For related compounds, see: Oliveira & Nunes (2006 ); Silva et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₂BrN₃O₂S
M_r = 390.26
Monoclinic, C 2/c
a = 32.149 (3) Å
b = 7.011 (1) Å
c = 16.589 (2) Å
β = 117.86 (1)°
V = 3305.7 (7) Å³
Z = 8
Cu Kα radiation
μ = 4.68 mm⁻¹
T = 299 K
0.65 × 0.28 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.147, T_max = 0.626
3889 measured reflections
2942 independent reflections
2677 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.147
S = 1.05
2942 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1—H1N⋯N3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10—H10⋯O2ⁱⁱ	0.93	2.57	3.395 (4)	149
C12—H12⋯O2ⁱⁱ	0.93	2.50	3.361 (5)	154
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: CAD-4-PC (Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008848/im2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008848/im2087Isup2.hkl

checkCIF report

Comment top

In the present work, the title compound has been synthesized to investigate its biological activity. Quinoline derivatives have been shown to be active against parasites. The quinine, for example, has been used as antimalarial drug years ago (Dueñas-Romero et al., 2007). Recently, studies showed that quinoline sulfonic acid derivatives are active in assays with Leishmania spp (da Silva et al., 2007). As part of our screening programs to investigate antiparasitic activity of quinoline derivatives, we report here a X-ray crystallographic study of the title compound (I). In the molecule of (I) (Fig. 1) the torsional angle of the central bridge S1—N1—N2—C10 is 144.8 (2)° and the plane of the quinoline ring system encloses a dihedral angle of 87.4 (1)° with the plane of the bromophenyl group. The NH group shows an intermolecular hydrogen bond towards the sulfonyl oxygen atom O1 [N—H···O = 2.18 (4) Å] and an intramolecular hydrogen bond to N3 [N—H···N = 2.36 (3) Å] leading to a bifurcated hydrogen bond. C10 and C12 have an intermolecular contact towards the sulfonyloxygen atom O2 [C—H···O = 2.57 (3) Å, C—H···O = 2.50 (3) Å, respectively] (Table 1).

Related literature top

For general background, see: Dueñas-Romero et al. (2007); da Silva et al. (2007). For related compounds, see: Oliveira & Nunes (2006); Silva et al. (2002006).

Experimental top

The title compound (I) was synthesized by the reaction of p- bromobenzaldehyde (0.89 mmol, 160 mg) with quinoline-8-sulfonylhydrazide (0.89 mmol, 200 mg). The reaction was carried out in ethyl alcohol acidified with two drops of hydrochloric acid, as described for similar compounds (Oliveira et al., 2006; Silva et al., 2006). The mixture was stirred at room temperature for 4 h. After that, the solution was diluted with water and the resulting solid was filtered. The crystal used for data collection was obtained by dissolving 188 mg of (I) in 25 ml of ethyl alcohol and cooling down the solution to room temperature.

Computing details top

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC (Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonds shown as dashed lines.

N'-(4-Bromobenzylidene)quinoline-8-sulfonohydrazide top

Crystal data top

C₁₆H₁₂BrN₃O₂S	F(000) = 1568
M_r = 390.26	D_x = 1.568 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 32.149 (3) Å	θ = 3.1–20.6°
b = 7.011 (1) Å	µ = 4.68 mm⁻¹
c = 16.589 (2) Å	T = 299 K
β = 117.86 (1)°	Long plate, colorless
V = 3305.7 (7) Å³	0.65 × 0.28 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 66.9°, θ_min = 3.1°
ω/2θ scans	h = −36→38
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
T_min = 0.147, T_max = 0.626	l = −19→4
3889 measured reflections	3 standard reflections every 120 min
2942 independent reflections	intensity decay: 1.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0805P)² + 6.9219P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.007
2942 reflections	Δρ_max = 0.75 e Å⁻³
212 parameters	Δρ_min = −1.00 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00043 (7)

Crystal data top

C₁₆H₁₂BrN₃O₂S	V = 3305.7 (7) Å³
M_r = 390.26	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 32.149 (3) Å	µ = 4.68 mm⁻¹
b = 7.011 (1) Å	T = 299 K
c = 16.589 (2) Å	0.65 × 0.28 × 0.10 mm
β = 117.86 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2677 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.147, T_max = 0.626	3 standard reflections every 120 min
3889 measured reflections	intensity decay: 1.5%
2942 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.75 e Å⁻³
2942 reflections	Δρ_min = −1.00 e Å⁻³
212 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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
Br1	−0.070685 (17)	−0.11247 (10)	0.09298 (5)	0.0984 (3)
S1	0.19475 (2)	0.54754 (10)	0.16299 (5)	0.0399 (2)
O1	0.24468 (8)	0.5560 (3)	0.20074 (15)	0.0506 (6)
O2	0.16963 (9)	0.7062 (3)	0.17320 (17)	0.0550 (6)
N1	0.18486 (8)	0.3613 (4)	0.21089 (16)	0.0383 (5)
H1N	0.2045 (13)	0.269 (6)	0.214 (2)	0.046*
N2	0.13725 (8)	0.3233 (4)	0.18004 (16)	0.0401 (5)
N3	0.20861 (9)	0.1911 (4)	0.07924 (17)	0.0454 (6)
C1	0.17125 (10)	0.4981 (4)	0.04547 (19)	0.0406 (6)
C2	0.14454 (13)	0.6347 (5)	−0.0160 (2)	0.0535 (8)
H2	0.1358	0.7442	0.0039	0.064*
C3	0.13046 (15)	0.6088 (6)	−0.1090 (3)	0.0670 (11)
H3	0.1119	0.7007	−0.1508	0.080*
C4	0.14362 (15)	0.4515 (6)	−0.1386 (2)	0.0646 (11)
H4	0.1348	0.4384	−0.2003	0.077*
C5	0.17042 (12)	0.3077 (5)	−0.0775 (2)	0.0501 (8)
C6	0.18600 (15)	0.1403 (6)	−0.1035 (3)	0.0624 (10)
H6	0.1789	0.1220	−0.1641	0.075*
C7	0.21095 (14)	0.0087 (6)	−0.0407 (3)	0.0638 (10)
H7	0.2216	−0.1004	−0.0573	0.077*
C8	0.22084 (13)	0.0368 (5)	0.0498 (3)	0.0552 (8)
H8	0.2370	−0.0587	0.0918	0.066*
C9	0.18388 (10)	0.3272 (4)	0.01633 (19)	0.0405 (6)
C10	0.12657 (11)	0.1475 (5)	0.1748 (2)	0.0424 (7)
H10	0.1494	0.0554	0.1854	0.051*
C11	0.07855 (12)	0.0890 (5)	0.1521 (2)	0.0467 (7)
C12	0.06707 (15)	−0.1023 (6)	0.1405 (3)	0.0679 (11)
H12	0.0894	−0.1918	0.1449	0.082*
C13	0.02227 (16)	−0.1614 (7)	0.1221 (4)	0.0785 (12)
H13	0.0145	−0.2903	0.1142	0.094*
C14	−0.01013 (13)	−0.0307 (6)	0.1158 (3)	0.0639 (10)
C15	0.00053 (14)	0.1602 (7)	0.1269 (3)	0.0758 (12)
H15	−0.0220	0.2487	0.1224	0.091*
C16	0.04473 (13)	0.2196 (6)	0.1446 (3)	0.0657 (10)
H16	0.0519	0.3489	0.1516	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0546 (3)	0.1028 (5)	0.1379 (6)	−0.0215 (3)	0.0451 (3)	0.0083 (3)
S1	0.0378 (4)	0.0351 (4)	0.0470 (4)	−0.0033 (3)	0.0202 (3)	−0.0071 (3)
O1	0.0393 (12)	0.0493 (13)	0.0586 (12)	−0.0131 (10)	0.0189 (10)	−0.0155 (10)
O2	0.0625 (14)	0.0372 (11)	0.0706 (14)	0.0061 (11)	0.0356 (12)	−0.0071 (10)
N1	0.0326 (12)	0.0390 (13)	0.0421 (12)	0.0041 (10)	0.0164 (10)	0.0014 (10)
N2	0.0346 (12)	0.0430 (14)	0.0435 (12)	0.0001 (11)	0.0189 (10)	−0.0027 (10)
N3	0.0453 (14)	0.0429 (14)	0.0519 (14)	−0.0017 (12)	0.0259 (12)	−0.0043 (11)
C1	0.0401 (15)	0.0382 (15)	0.0444 (15)	−0.0080 (12)	0.0206 (12)	−0.0009 (12)
C2	0.0531 (19)	0.0418 (17)	0.0601 (19)	−0.0021 (15)	0.0219 (16)	0.0094 (14)
C3	0.070 (3)	0.063 (2)	0.056 (2)	−0.0072 (19)	0.0195 (18)	0.0198 (18)
C4	0.071 (2)	0.077 (3)	0.0429 (17)	−0.024 (2)	0.0244 (17)	0.0044 (17)
C5	0.0496 (17)	0.061 (2)	0.0467 (16)	−0.0209 (16)	0.0282 (14)	−0.0089 (15)
C6	0.071 (2)	0.070 (2)	0.061 (2)	−0.027 (2)	0.0441 (19)	−0.0252 (19)
C7	0.065 (2)	0.060 (2)	0.082 (3)	−0.0125 (19)	0.047 (2)	−0.026 (2)
C8	0.0527 (19)	0.0480 (19)	0.074 (2)	−0.0014 (15)	0.0368 (17)	−0.0094 (16)
C9	0.0375 (14)	0.0438 (16)	0.0446 (15)	−0.0112 (13)	0.0227 (12)	−0.0029 (12)
C10	0.0392 (15)	0.0413 (16)	0.0469 (15)	0.0020 (13)	0.0203 (13)	0.0002 (12)
C11	0.0424 (16)	0.0472 (17)	0.0517 (16)	−0.0041 (14)	0.0231 (14)	0.0008 (13)
C12	0.055 (2)	0.048 (2)	0.104 (3)	−0.0022 (16)	0.039 (2)	0.0016 (19)
C13	0.062 (2)	0.053 (2)	0.121 (4)	−0.014 (2)	0.043 (2)	−0.002 (2)
C14	0.0454 (19)	0.070 (3)	0.075 (2)	−0.0129 (18)	0.0271 (17)	0.0046 (19)
C15	0.048 (2)	0.068 (3)	0.112 (3)	0.0004 (19)	0.038 (2)	−0.003 (2)
C16	0.0480 (19)	0.049 (2)	0.098 (3)	−0.0031 (17)	0.0332 (19)	−0.004 (2)

Geometric parameters (Å, º) top

Br1—C14	1.890 (4)	C5—C6	1.420 (5)
S1—O1	1.426 (2)	C6—C7	1.342 (6)
S1—O2	1.431 (2)	C6—H6	0.9300
S1—N1	1.635 (3)	C7—C8	1.395 (5)
S1—C1	1.765 (3)	C7—H7	0.9300
N1—N2	1.394 (3)	C8—H8	0.9300
N1—H1N	0.89 (4)	C10—C11	1.467 (4)
N2—C10	1.271 (4)	C10—H10	0.9300
N3—C8	1.320 (4)	C11—C12	1.380 (5)
N3—C9	1.362 (4)	C11—C16	1.382 (5)
C1—C2	1.369 (5)	C12—C13	1.389 (6)
C1—C9	1.421 (4)	C12—H12	0.9300
C2—C3	1.403 (5)	C13—C14	1.354 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.353 (6)	C14—C15	1.373 (6)
C3—H3	0.9300	C15—C16	1.374 (5)
C4—C5	1.403 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C9	1.413 (4)

O1—S1—O2	119.85 (14)	C6—C7—H7	120.3
O1—S1—N1	104.74 (14)	C8—C7—H7	120.3
O2—S1—N1	108.35 (14)	N3—C8—C7	123.7 (4)
O1—S1—C1	107.83 (14)	N3—C8—H8	118.1
O2—S1—C1	108.02 (15)	C7—C8—H8	118.1
N1—S1—C1	107.45 (13)	N3—C9—C5	123.0 (3)
N2—N1—S1	113.80 (19)	N3—C9—C1	119.2 (3)
N2—N1—H1N	121 (2)	C5—C9—C1	117.8 (3)
S1—N1—H1N	108 (2)	N2—C10—C11	120.5 (3)
C10—N2—N1	115.2 (3)	N2—C10—H10	119.8
C8—N3—C9	117.3 (3)	C11—C10—H10	119.8
C2—C1—C9	121.1 (3)	C12—C11—C16	118.9 (3)
C2—C1—S1	118.7 (3)	C12—C11—C10	119.2 (3)
C9—C1—S1	119.9 (2)	C16—C11—C10	121.8 (3)
C1—C2—C3	119.7 (4)	C11—C12—C13	120.2 (4)
C1—C2—H2	120.1	C11—C12—H12	119.9
C3—C2—H2	120.1	C13—C12—H12	119.9
C4—C3—C2	120.6 (4)	C14—C13—C12	119.8 (4)
C4—C3—H3	119.7	C14—C13—H13	120.1
C2—C3—H3	119.7	C12—C13—H13	120.1
C3—C4—C5	121.0 (3)	C13—C14—C15	121.0 (4)
C3—C4—H4	119.5	C13—C14—Br1	119.6 (3)
C5—C4—H4	119.5	C15—C14—Br1	119.5 (3)
C4—C5—C9	119.6 (3)	C14—C15—C16	119.5 (4)
C4—C5—C6	124.0 (3)	C14—C15—H15	120.2
C9—C5—C6	116.4 (3)	C16—C15—H15	120.2
C7—C6—C5	120.0 (3)	C15—C16—C11	120.7 (4)
C7—C6—H6	120.0	C15—C16—H16	119.7
C5—C6—H6	120.0	C11—C16—H16	119.7
C6—C7—C8	119.5 (3)

O1—S1—N1—N2	−177.68 (19)	C8—N3—C9—C1	−178.1 (3)
O2—S1—N1—N2	53.3 (2)	C4—C5—C9—N3	177.9 (3)
C1—S1—N1—N2	−63.2 (2)	C6—C5—C9—N3	−2.9 (4)
S1—N1—N2—C10	144.8 (2)	C4—C5—C9—C1	−2.8 (4)
O1—S1—C1—C2	−113.8 (3)	C6—C5—C9—C1	176.4 (3)
O2—S1—C1—C2	17.1 (3)	C2—C1—C9—N3	−176.9 (3)
N1—S1—C1—C2	133.8 (3)	S1—C1—C9—N3	9.3 (4)
O1—S1—C1—C9	60.2 (3)	C2—C1—C9—C5	3.7 (4)
O2—S1—C1—C9	−168.9 (2)	S1—C1—C9—C5	−170.1 (2)
N1—S1—C1—C9	−52.2 (3)	N1—N2—C10—C11	173.8 (2)
C9—C1—C2—C3	−1.9 (5)	N2—C10—C11—C12	175.4 (3)
S1—C1—C2—C3	172.0 (3)	N2—C10—C11—C16	−6.5 (5)
C1—C2—C3—C4	−1.0 (6)	C16—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	2.0 (6)	C10—C11—C12—C13	177.7 (4)
C3—C4—C5—C9	0.0 (5)	C11—C12—C13—C14	−0.1 (7)
C3—C4—C5—C6	−179.1 (4)	C12—C13—C14—C15	0.3 (7)
C4—C5—C6—C7	−179.1 (3)	C12—C13—C14—Br1	−178.9 (4)
C9—C5—C6—C7	1.8 (5)	C13—C14—C15—C16	0.0 (7)
C5—C6—C7—C8	0.8 (6)	Br1—C14—C15—C16	179.2 (3)
C9—N3—C8—C7	1.8 (5)	C14—C15—C16—C11	−0.5 (7)
C6—C7—C8—N3	−2.8 (6)	C12—C11—C16—C15	0.8 (6)
C8—N3—C9—C5	1.2 (4)	C10—C11—C16—C15	−177.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1—H1N···N3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10—H10···O2ⁱⁱ	0.93	2.57	3.395 (4)	149
C12—H12···O2ⁱⁱ	0.93	2.50	3.361 (5)	154

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrN₃O₂S
M_r	390.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	32.149 (3), 7.011 (1), 16.589 (2)
β (°)	117.86 (1)
V (Å³)	3305.7 (7)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	4.68
Crystal size (mm)	0.65 × 0.28 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.147, 0.626
No. of measured, independent and observed [I > 2σ(I)] reflections	3889, 2942, 2677
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.147, 1.05
No. of reflections	2942
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.75, −1.00

Computer programs: CAD-4-PC (Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1—H1N···N3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10—H10···O2ⁱⁱ	0.93	2.57	3.395 (4)	148.7
C12—H12···O2ⁱⁱ	0.93	2.50	3.361 (5)	153.9

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

Acknowledgements

The authors thank Professor Dr Hartmut Fuess, FG Strukturforschung, Technische Universität Darmstadt, for diffractometer time.

References

Dueñas-Romero, A. M., Loiseau, P. M. & Saint-Pierre-Chazalet, M. (2006). Biochim. Biophys. Acta, 1768, 246–252. Web of Science PubMed Google Scholar
Nonius (1996). CAD-4-PC. Nonius GmbH, Solingen, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Oliveira, K. N. de & Nunes, R. J. (2006). Synth. Commun. 36, 3401–3409. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, L. L., de Oliveira, K. N. & Nunes, R. J. (2006). Arkivoc, xiii, 124–129. CrossRef Google Scholar
Silva, L. E. da, Joussef, A. C., Pacheco, L. K., Duarte, A. M. C., Steindel, M. & Rebelo, R. A. (2007). Bioorg. Med. Chem. 15, 7553–7560. Web of Science PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar