organic compounds
2-[(E)-2-(3,4-Dichlorobenzylidene)hydrazin-1-yl]quinoxaline
aFundação Oswaldo Cruz, Instituto de Tecnologia em, Fármacos–Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos 21041-250, Rio de Janeiro, RJ, Brazil, bChemistry Department, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
The 21 non-H atoms of the title compound, C15H10Cl2N4, are almost planar (r.m.s. deviation = 0.032 Å); the conformation about the N=C bond [1.277 (6) Å] is E. In the crystal, zigzag supramolecular chains along the c axis (glide symmetry) are formed via N—H⋯N hydrogen bonds. These associate along the b axis by π–π interactions between the fused and terminal benzene rings [intercentroid distance = 3.602 (3) Å] so that layers form in the bc plane.
CCDC reference: 980593
Related literature
For the use of quinoxaline compounds as dyestuffs and biological agents, see: Mielcke et al. (2012); Mamedov & Zhukova (2012); Rodrigues et al. (2014). For a related hydrazone structure, see: de Souza et al. (2013).
Experimental
Crystal data
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Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 980593
10.1107/S1600536814000415/hg5372sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000415/hg5372Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000415/hg5372Isup3.cml
A solution of 2-hydrazinylquinozaline (1 mmol) and 3,4-dichlorobenzaldehyde (1.05 mmol) in EtOH (10 ml) was stirred at room temperature for 24 h and rotary evaporated. The residue was washed with ice-cold EtOH (3 ×) and recrystallized from its MeOCH2CH2OH solution. Yield: 95%. M.Pt: 528–529 K. 1H NMR (400 MHz, DMSO-d6): δ 11.86 (1H, s, NH); 9.15 (1H, s, H3); 8.11 (1H, s, CH); 8.04 (1H, d, J = 2.0; H2'); 7.93 (1H, d, J = 8.2, H5); 7.77 (1H, dd, J = 8.4 and J = 2.0, H6'); 7.68 (3H, m, H5', H7 and H8); 7.51 (1H, dt, J = 8.2 and J = 2.0, H6) ppm. 13C NMR (100 MHz, DMSO-d6): δ 150.0; 140.7; 139.0; 138.0; 136.4; 135.5; 131.6; 131.1; 130.8; 130.3; 128.7; 127.8; 126.3; 126.2; 125.3 ppm. MS/ESI (M—H): 314.9. IR (cm-1, KBr): 3437 ν(N—H); 1585 ν(C═N).
Intensity data was collected at the National Crystallographic Service, England (Coles & Gale, 2012). The C–bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The N-bound H atom was located from a difference map and refined with Uiso(H) = 1.2Ueq(N).
Quinoxaline compounds have found uses, mainly as biologically active compounds, but also as dyestuffs (Mielcke et al., 2012; Mamedov & Zhukova, 2012). The biological activities of quinoxaline compounds include anti-bacterial, anti-tubercular, anti-microbial, anti-fungal, anti-malarial, anti-inflammatory, anti-leishmanial, anti-tumour, herbicidal and insecticidal (Mielcke et al., 2012; Mamedov & Zhukova, 2012). In a recent study, an evaluation of the anti-cancer activities of a series of (E)-2-(2-benzylidene)hydrazinyl)quinoxaline derivatives was reported (Rodrigues et al., 2014). As part of our continuing studies on the structures of biologically active
(de Souza et al., 2013), we now report the of the title compound, (E)-2-(2-(3,4-dichlorobenzylidene)hydrazinyl)-quinoxaline, (I).In (I), Fig. 1, the 21 non-hydorgen atoms comprising the molecule are co-planar with the r.m.s. deviation = 0.032 Å; the maximum deviations from the least-squares plane are 0.066 (5) Å for atom C5 and -0.057 (1) Å for atom Cl2. The conformation about the N1═C7 bond [1.277 (6) Å] is E.
In the crystal packing, zigzag supramoelcular chains (glide symmetry) are formed via N—H···N hydrogen bonds, Fig. 2 and Table 1. These chains along the c direction are consolidated into supramolecular layers in the bc plane by π—π interactions between the (C1–C6) and (C9–C14)i rings [inter-centroid distance = 3.602 (3) Å, inter-planar angle = 2.4 (2)° for i: 1-x, 1-y, -z] formed along the b direction, Fig. 3.
Quinoxaline compounds have found uses, mainly as biologically active compounds, but also as dyestuffs (Mielcke et al., 2012; Mamedov & Zhukova, 2012). The biological activities of quinoxaline compounds include anti-bacterial, anti-tubercular, anti-microbial, anti-fungal, anti-malarial, anti-inflammatory, anti-leishmanial, anti-tumour, herbicidal and insecticidal (Mielcke et al., 2012; Mamedov & Zhukova, 2012). In a recent study, an evaluation of the anti-cancer activities of a series of (E)-2-(2-benzylidene)hydrazinyl)quinoxaline derivatives was reported (Rodrigues et al., 2014). As part of our continuing studies on the structures of biologically active
(de Souza et al., 2013), we now report the of the title compound, (E)-2-(2-(3,4-dichlorobenzylidene)hydrazinyl)-quinoxaline, (I).In (I), Fig. 1, the 21 non-hydorgen atoms comprising the molecule are co-planar with the r.m.s. deviation = 0.032 Å; the maximum deviations from the least-squares plane are 0.066 (5) Å for atom C5 and -0.057 (1) Å for atom Cl2. The conformation about the N1═C7 bond [1.277 (6) Å] is E.
In the crystal packing, zigzag supramoelcular chains (glide symmetry) are formed via N—H···N hydrogen bonds, Fig. 2 and Table 1. These chains along the c direction are consolidated into supramolecular layers in the bc plane by π—π interactions between the (C1–C6) and (C9–C14)i rings [inter-centroid distance = 3.602 (3) Å, inter-planar angle = 2.4 (2)° for i: 1-x, 1-y, -z] formed along the b direction, Fig. 3.
For the use of quinoxaline compounds as dyestuffs and biological agents, see: Mielcke et al. (2012); Mamedov & Zhukova (2012); Rodrigues et al. (2014). For a related hydrazone structure, see: de Souza et al. (2013).
A solution of 2-hydrazinylquinozaline (1 mmol) and 3,4-dichlorobenzaldehyde (1.05 mmol) in EtOH (10 ml) was stirred at room temperature for 24 h and rotary evaporated. The residue was washed with ice-cold EtOH (3 ×) and recrystallized from its MeOCH2CH2OH solution. Yield: 95%. M.Pt: 528–529 K. 1H NMR (400 MHz, DMSO-d6): δ 11.86 (1H, s, NH); 9.15 (1H, s, H3); 8.11 (1H, s, CH); 8.04 (1H, d, J = 2.0; H2'); 7.93 (1H, d, J = 8.2, H5); 7.77 (1H, dd, J = 8.4 and J = 2.0, H6'); 7.68 (3H, m, H5', H7 and H8); 7.51 (1H, dt, J = 8.2 and J = 2.0, H6) ppm. 13C NMR (100 MHz, DMSO-d6): δ 150.0; 140.7; 139.0; 138.0; 136.4; 135.5; 131.6; 131.1; 130.8; 130.3; 128.7; 127.8; 126.3; 126.2; 125.3 ppm. MS/ESI (M—H): 314.9. IR (cm-1, KBr): 3437 ν(N—H); 1585 ν(C═N).
detailsIntensity data was collected at the National Crystallographic Service, England (Coles & Gale, 2012). The C–bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The N-bound H atom was located from a difference map and refined with Uiso(H) = 1.2Ueq(N).
Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell
CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C15H10Cl2N4 | F(000) = 648 |
Mr = 317.17 | Dx = 1.526 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5450 reflections |
a = 16.0284 (11) Å | θ = 3.2–29.1° |
b = 6.9756 (4) Å | µ = 0.47 mm−1 |
c = 12.4127 (9) Å | T = 120 K |
β = 96.043 (7)° | Prism, yellow |
V = 1380.12 (16) Å3 | 0.20 × 0.13 × 0.03 mm |
Z = 4 |
Rigaku RAXIS conversion diffractometer | 2385 independent reflections |
Radiation source: Sealed Tube | 1670 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 25.0°, θmin = 3.2° |
profile data from ω–scans | h = −19→17 |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | k = −8→7 |
Tmin = 0.654, Tmax = 1.000 | l = −14→14 |
7037 measured reflections |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.219 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | w = 1/[σ2(Fo2) + (0.1005P)2 + 2.9896P] where P = (Fo2 + 2Fc2)/3 |
2385 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
C15H10Cl2N4 | V = 1380.12 (16) Å3 |
Mr = 317.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.0284 (11) Å | µ = 0.47 mm−1 |
b = 6.9756 (4) Å | T = 120 K |
c = 12.4127 (9) Å | 0.20 × 0.13 × 0.03 mm |
β = 96.043 (7)° |
Rigaku RAXIS conversion diffractometer | 2385 independent reflections |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | 1670 reflections with I > 2σ(I) |
Tmin = 0.654, Tmax = 1.000 | Rint = 0.043 |
7037 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.219 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.76 e Å−3 |
2385 reflections | Δρmin = −0.65 e Å−3 |
193 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.92037 (8) | 0.4044 (2) | 0.39515 (10) | 0.0391 (4) | |
Cl2 | 1.01377 (8) | 0.3943 (2) | 0.18221 (11) | 0.0391 (4) | |
N1 | 0.6096 (2) | 0.6684 (6) | 0.0737 (3) | 0.0234 (9) | |
N2 | 0.5269 (2) | 0.7147 (6) | 0.0801 (3) | 0.0249 (9) | |
H2N | 0.504 (3) | 0.718 (7) | 0.145 (4) | 0.030* | |
N3 | 0.3991 (2) | 0.8161 (5) | 0.0034 (3) | 0.0206 (9) | |
N4 | 0.4593 (2) | 0.8165 (6) | −0.2031 (3) | 0.0247 (9) | |
C1 | 0.7406 (3) | 0.5710 (7) | 0.1655 (4) | 0.0256 (11) | |
C2 | 0.7839 (3) | 0.5206 (7) | 0.2653 (4) | 0.0244 (11) | |
H2 | 0.7560 | 0.5212 | 0.3291 | 0.029* | |
C3 | 0.8691 (3) | 0.4690 (7) | 0.2706 (4) | 0.0307 (12) | |
C4 | 0.9107 (3) | 0.4672 (7) | 0.1782 (4) | 0.0281 (11) | |
C5 | 0.8680 (3) | 0.5232 (7) | 0.0788 (4) | 0.0301 (12) | |
H5 | 0.8963 | 0.5262 | 0.0154 | 0.036* | |
C6 | 0.7837 (3) | 0.5744 (7) | 0.0738 (4) | 0.0291 (11) | |
H6 | 0.7549 | 0.6125 | 0.0064 | 0.035* | |
C7 | 0.6523 (3) | 0.6206 (7) | 0.1623 (4) | 0.0235 (11) | |
H7 | 0.6259 | 0.6175 | 0.2273 | 0.028* | |
C8 | 0.4770 (3) | 0.7668 (6) | −0.0107 (3) | 0.0203 (10) | |
C9 | 0.3477 (3) | 0.8652 (6) | −0.0881 (3) | 0.0215 (10) | |
C10 | 0.2636 (3) | 0.9113 (7) | −0.0786 (4) | 0.0225 (10) | |
H10 | 0.2431 | 0.9085 | −0.0095 | 0.027* | |
C11 | 0.2105 (3) | 0.9607 (7) | −0.1694 (4) | 0.0253 (11) | |
H11 | 0.1536 | 0.9921 | −0.1625 | 0.030* | |
C12 | 0.2405 (3) | 0.9648 (7) | −0.2726 (4) | 0.0272 (11) | |
H12 | 0.2038 | 0.9993 | −0.3347 | 0.033* | |
C13 | 0.3230 (3) | 0.9187 (7) | −0.2832 (3) | 0.0233 (10) | |
H13 | 0.3430 | 0.9218 | −0.3526 | 0.028* | |
C14 | 0.3777 (3) | 0.8671 (6) | −0.1917 (4) | 0.0214 (10) | |
C15 | 0.5066 (3) | 0.7679 (7) | −0.1146 (3) | 0.0222 (10) | |
H15 | 0.5631 | 0.7319 | −0.1202 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0337 (8) | 0.0532 (9) | 0.0288 (7) | 0.0025 (6) | −0.0040 (5) | 0.0098 (6) |
Cl2 | 0.0250 (7) | 0.0496 (9) | 0.0422 (8) | 0.0038 (6) | 0.0012 (6) | 0.0045 (6) |
N1 | 0.022 (2) | 0.029 (2) | 0.0190 (19) | 0.0013 (17) | 0.0001 (16) | −0.0014 (17) |
N2 | 0.025 (2) | 0.037 (2) | 0.0130 (19) | 0.0015 (19) | 0.0014 (16) | 0.0009 (17) |
N3 | 0.020 (2) | 0.026 (2) | 0.0155 (18) | −0.0015 (17) | −0.0006 (15) | −0.0013 (16) |
N4 | 0.026 (2) | 0.030 (2) | 0.0177 (19) | 0.0012 (19) | 0.0034 (16) | −0.0016 (17) |
C1 | 0.025 (3) | 0.024 (2) | 0.027 (3) | 0.003 (2) | 0.000 (2) | 0.000 (2) |
C2 | 0.024 (2) | 0.032 (3) | 0.015 (2) | 0.003 (2) | −0.0031 (18) | 0.000 (2) |
C3 | 0.033 (3) | 0.021 (2) | 0.035 (3) | −0.009 (2) | −0.007 (2) | 0.002 (2) |
C4 | 0.024 (2) | 0.030 (3) | 0.029 (3) | −0.002 (2) | 0.000 (2) | 0.001 (2) |
C5 | 0.031 (3) | 0.033 (3) | 0.027 (3) | 0.000 (2) | 0.002 (2) | 0.000 (2) |
C6 | 0.028 (3) | 0.033 (3) | 0.026 (3) | −0.005 (2) | 0.002 (2) | −0.003 (2) |
C7 | 0.027 (3) | 0.030 (3) | 0.013 (2) | 0.002 (2) | −0.0005 (18) | −0.0013 (19) |
C8 | 0.027 (2) | 0.021 (2) | 0.012 (2) | −0.001 (2) | 0.0000 (18) | −0.0011 (17) |
C9 | 0.027 (2) | 0.022 (2) | 0.015 (2) | −0.002 (2) | 0.0009 (18) | −0.0037 (18) |
C10 | 0.023 (2) | 0.029 (3) | 0.015 (2) | −0.001 (2) | 0.0025 (18) | −0.0006 (19) |
C11 | 0.023 (2) | 0.028 (3) | 0.024 (3) | 0.001 (2) | 0.0002 (19) | −0.002 (2) |
C12 | 0.035 (3) | 0.027 (3) | 0.017 (2) | −0.002 (2) | −0.009 (2) | 0.0006 (19) |
C13 | 0.027 (3) | 0.032 (3) | 0.011 (2) | 0.002 (2) | 0.0001 (18) | −0.0005 (19) |
C14 | 0.022 (2) | 0.024 (2) | 0.019 (2) | 0.001 (2) | 0.0012 (18) | −0.0025 (19) |
C15 | 0.025 (2) | 0.028 (2) | 0.014 (2) | 0.003 (2) | −0.0018 (17) | −0.0006 (19) |
Cl1—C3 | 1.733 (5) | C5—C6 | 1.393 (7) |
Cl2—C4 | 1.725 (5) | C5—H5 | 0.9500 |
N1—C7 | 1.277 (6) | C6—H6 | 0.9500 |
N1—N2 | 1.375 (5) | C7—H7 | 0.9500 |
N2—C8 | 1.361 (6) | C8—C15 | 1.421 (6) |
N2—H2N | 0.92 (5) | C9—C10 | 1.402 (6) |
N3—C8 | 1.323 (6) | C9—C14 | 1.420 (6) |
N3—C9 | 1.375 (6) | C10—C11 | 1.383 (6) |
N4—C15 | 1.312 (6) | C10—H10 | 0.9500 |
N4—C14 | 1.378 (6) | C11—C12 | 1.414 (6) |
C1—C6 | 1.392 (7) | C11—H11 | 0.9500 |
C1—C2 | 1.400 (6) | C12—C13 | 1.381 (7) |
C1—C7 | 1.453 (6) | C12—H12 | 0.9500 |
C2—C3 | 1.406 (7) | C13—C14 | 1.406 (6) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.385 (7) | C15—H15 | 0.9500 |
C4—C5 | 1.401 (7) | ||
C7—N1—N2 | 116.3 (4) | C1—C7—H7 | 119.4 |
C8—N2—N1 | 120.1 (4) | N3—C8—N2 | 116.1 (4) |
C8—N2—H2N | 118 (3) | N3—C8—C15 | 121.9 (4) |
N1—N2—H2N | 122 (3) | N2—C8—C15 | 122.0 (4) |
C8—N3—C9 | 116.6 (4) | N3—C9—C10 | 119.1 (4) |
C15—N4—C14 | 116.8 (4) | N3—C9—C14 | 121.3 (4) |
C6—C1—C2 | 119.0 (4) | C10—C9—C14 | 119.6 (4) |
C6—C1—C7 | 122.6 (4) | C11—C10—C9 | 120.2 (4) |
C2—C1—C7 | 118.3 (4) | C11—C10—H10 | 119.9 |
C1—C2—C3 | 119.6 (4) | C9—C10—H10 | 119.9 |
C1—C2—H2 | 120.2 | C10—C11—C12 | 120.3 (4) |
C3—C2—H2 | 120.2 | C10—C11—H11 | 119.9 |
C4—C3—C2 | 120.8 (4) | C12—C11—H11 | 119.9 |
C4—C3—Cl1 | 120.8 (4) | C13—C12—C11 | 120.1 (4) |
C2—C3—Cl1 | 118.4 (4) | C13—C12—H12 | 119.9 |
C3—C4—C5 | 119.5 (5) | C11—C12—H12 | 119.9 |
C3—C4—Cl2 | 121.4 (4) | C12—C13—C14 | 120.3 (4) |
C5—C4—Cl2 | 119.0 (4) | C12—C13—H13 | 119.9 |
C6—C5—C4 | 119.5 (5) | C14—C13—H13 | 119.9 |
C6—C5—H5 | 120.2 | N4—C14—C13 | 120.0 (4) |
C4—C5—H5 | 120.2 | N4—C14—C9 | 120.5 (4) |
C1—C6—C5 | 121.4 (5) | C13—C14—C9 | 119.5 (4) |
C1—C6—H6 | 119.3 | N4—C15—C8 | 122.9 (4) |
C5—C6—H6 | 119.3 | N4—C15—H15 | 118.5 |
N1—C7—C1 | 121.1 (4) | C8—C15—H15 | 118.5 |
N1—C7—H7 | 119.4 | ||
C7—N1—N2—C8 | −179.9 (4) | N1—N2—C8—C15 | 2.6 (7) |
C6—C1—C2—C3 | −1.9 (7) | C8—N3—C9—C10 | 177.5 (4) |
C7—C1—C2—C3 | 179.0 (4) | C8—N3—C9—C14 | −1.5 (6) |
C1—C2—C3—C4 | −0.1 (7) | N3—C9—C10—C11 | −179.8 (4) |
C1—C2—C3—Cl1 | −179.2 (4) | C14—C9—C10—C11 | −0.8 (7) |
C2—C3—C4—C5 | 2.0 (7) | C9—C10—C11—C12 | 0.2 (7) |
Cl1—C3—C4—C5 | −178.9 (4) | C10—C11—C12—C13 | 0.2 (7) |
C2—C3—C4—Cl2 | −177.1 (4) | C11—C12—C13—C14 | 0.1 (7) |
Cl1—C3—C4—Cl2 | 1.9 (6) | C15—N4—C14—C13 | −179.2 (4) |
C3—C4—C5—C6 | −1.9 (8) | C15—N4—C14—C9 | −0.1 (7) |
Cl2—C4—C5—C6 | 177.2 (4) | C12—C13—C14—N4 | 178.3 (4) |
C2—C1—C6—C5 | 2.0 (7) | C12—C13—C14—C9 | −0.8 (7) |
C7—C1—C6—C5 | −179.0 (5) | N3—C9—C14—N4 | 1.0 (7) |
C4—C5—C6—C1 | −0.1 (8) | C10—C9—C14—N4 | −178.0 (4) |
N2—N1—C7—C1 | −179.3 (4) | N3—C9—C14—C13 | −179.8 (4) |
C6—C1—C7—N1 | 0.7 (7) | C10—C9—C14—C13 | 1.2 (7) |
C2—C1—C7—N1 | 179.8 (4) | C14—N4—C15—C8 | −0.2 (7) |
C9—N3—C8—N2 | −178.7 (4) | N3—C8—C15—N4 | −0.3 (7) |
C9—N3—C8—C15 | 1.2 (6) | N2—C8—C15—N4 | 179.6 (4) |
N1—N2—C8—N3 | −177.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N4i | 0.92 (5) | 2.10 (5) | 3.013 (5) | 171 (4) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N4i | 0.92 (5) | 2.10 (5) | 3.013 (5) | 171 (4) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Footnotes
‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
Acknowledgements
The use of the EPSRC X-ray crystallographic service (Coles & Gale, 2012) at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Structural studies are supported by the Ministry of Higher Education (Malaysia) and the University of Malaya through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).
References
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Coles, S. J. & Gale, P. A. (2012). Chem. Sci, 3, 683–689. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mamedov, V. A. & Zhukova, N. A. (2012). Progress in Heterocyclic Chemistry, edited by G. W. Gribble & J. A. Joule, Vol. 24, ch. 2, pp. 55–88. Oxford: Elsevierd. Google Scholar
Mielcke, T. R., Mascarello, A., Fillipi-Chiela, E., Zanin, R. F., Lenz, G., Leal, P. C., Chirardia, L. D., Yunes, R. A., Nunes, R. J., Battastin, A. M. O., Marrone, F. B. & Campos, M. M. (2012). Eur. J. Med. Chem. 48, 255–264. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku (2012). CrystalClear-SM Expert. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rodrigues, F. A. R., Bomfim, I. S., Cavalcanti, B. C., Pessoa, C. O., Wardell, J. L., Wardell, S. M. S. V., Pinheiro, A. C., Kaiser, C. R., Nogueira, T. C. M., Low, J. N., Gomes, L. R. & de Souza, M. V. N. (2014). Bioorg. Med. Chem. Lett. Submitted. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Souza, M. V. N. de, Goncalves, R. S. B., Wardell, S. M. S. V. & Wardell, J. L. (2013). Z. Kristallogr. 228, 359–368. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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