organic compounds
1-Anilino-5-methyl-1H-1,2,3-triazole-4-carbaldehyde
aUniversidade Federal Fluminense, Departamento de Química Orgânica, Programa de Pós-Graduaçõ em Química, 24020-141 Niterói, RJ, Brazil, bUnidade Universitária de Farmácia, Fundaçõ Centro Universitário Estadual da Zona Oeste, 23070-200, Rio de Janeiro, RJ, Brazil, cFioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, dDepartment of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, and eCentre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my
The title compound, C10H10N4O, is twisted about the Nring—Namine bond with the dihedral angle between the 1,2,3-triazolyl and N-bound phenyl rings being 79.14 (9)°. The C-bound aldehyde group is coplanar with the triazolyl ring, with the N—C—C—O torsion angle being 3.5 (3)°. While coplanar, the aldehyde O atom is orientated in the opposite direction to the triazolyl-bound methyl group. The most prominent feature of the molecular packing is the formation of zigzag chains (glide symmetry) along the b axis and mediated by amine-N—H⋯N(triazolyl) hydrogen bonds. The chains are connected into supramolecular layers by phenyl- and methyl-C—H⋯O(aldehyde) interactions, with phenyl groups projecting to either side. Layers stack along the c axis with no directional interactions between them.
Keywords: crystal structure; 1,2,3-triazole; aldehyde; hydrogen bonding.
CCDC reference: 672061
Structure description
Interest in 1,2,3-triazoles relates, in part, to their biological activity (Dehaen & Bakulev, 2014). For example, compounds related to the title compound have been evaluated previously for activity against Cantagalo virus (Jordão et al., 2009) and for anti-tubercular activity (Jordão et al., 2011).
The title compound, Fig. 1, comprises two effectively co-planar regions. Thus, the aldehyde group connected at C1 is co-planar with the 1,2,3-triazolyl ring (r.m.s. deviation = 0.007 Å), forming a N4—C1—C10—O1 torsion angle of 3.5 (3)°. Indeed, the r.m.s. deviation of the least-squares plane through all non-hydrogen atoms in the molecule excluding those of the phenyl ring is 0.019 Å. The latter sits almost prime to the remainder of the molecule, forming a dihedral angle of 79.14 (9)° with the triazolyl ring. The aldehyde-O1 atom occupies a position anti with respect to the triazolyl-bound methyl group.
Amine-N—H⋯N(triazoyl) hydrogen bonds feature in the , and lead to supramolecular zigzag chains along the b axis. The chains thus formed are linked into a layer in the ab plane, Fig. 2, by phenyl-C—H⋯O(aldehyde) and methyl-C—H⋯O(aldehyde) interactions, indicating the aldehyde-O atom accepts two interactions. The phenyl groups lie to either side of the supramolecular layers that stack along the c axis. However, there are no directional interactions between successive layers.
Table 1
|
1,2,3-Triazole derivatives generated in the biological studies (e.g. Jordão et al., 2009) have provided crystals enabling delineation of the dependency of molecular packing patterns upon the of the substituents, i.e. N-arylamino-1,2,3-triazole (Cunha et al., 2013) and N-(arylamino)-1,2,3-triazole-4-carbohydrazides (Seth et al., 2015).
Synthesis and crystallization
To a solution of oxalyl chloride (3.00 mmol) in anhydrous CH2Cl2 (3.7 mL), maintained under nitrogen at −78°C, was added dropwise DMSO (0.42 mL, 6.0 mmol). After stirring for 15 mins, a solution of the precursor alcohol (Cunha et al., 2016; 1.00 mmol) in DMSO (2 mL), followed by anhydrous CH2Cl2 (6.0 mL), were added dropwise. The reaction mixture was maintained at −78°C for 90 mins and Me3N (1.05 mL, 1.0 mmol) was then added dropwise. After stirring for 20 mins, aqueous NaCl was added, and the organic layer was extracted and concentrated under reduced pressure. The resulting residue was column chromatographed using silica gel and ethyl acetate:hexane (3:7) as to give the pure triazole in 80% yield, as a yellow solid; m.p. 118–120°C. IR (KBr) νmax (cm−1) 3282 (N—H); 1689 (C=O). 1H NMR (300 MHz, CDCl3): δ 2.57 (s, 3H, CH3), 6.52 (dd, 2H, J = 0.9 and 8.5 Hz, H5 & H9), 7.04 (tt, 1H, J = 0.9 and 7.3 Hz, H7), 7.24–7.30 (m, 2H, H6 and H8), 7.66 (bs, 1H, N–H), 10.2 (s, 1H, CHO). 13C NMR (75 MHz, CDCl3): δ 8.3 (CH3), 113.7 (C5 & C9), 123.1 (C7), 129.5 (C6 & C8), 139.2 (C1 or C2), 142.2 (C1 or C2), 144.7 (C4), 186.0 (CHO). Anal. calcd. for C10H10N4O: C, 59.40; H, 4.98; N, 27.71. Found: C, 59.38; H, 4.95; N, 27.88.
Refinement
Crystal data, data collection and structure . Owing to poor agreement, a reflection, i.e. (2 1 2), was removed from the final cycles of refinement.
details are summarized in Table 2Structural data
CCDC reference: 672061
10.1107/S2414314616000389/zq4001sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616000389/zq4001Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616000389/zq4001Isup3.cml
Interest in 1,2,3-triazoles relates, in part, to their biological activity (Dehaen & Bakulev, 2014). For example, compounds related to the title compound have been evaluated previously for activity against Cantagalo virus (Jordão et al., 2009) and for anti-tubercular activity (Jordão et al., 2011).
The title compound, Fig. 1, comprises two effectively co-planar regions. Thus, the aldehyde group connected at C1 is co-planar with the 1,2,3-triazolyl ring (r.m.s. deviation = 0.007 Å), forming a N4—C1—C10—O1 torsion angle of 3.5 (3)°. Indeed, the r.m.s. deviation of the least-squares plane through all non-hydrogen atoms in the molecule excluding those of the phenyl ring is 0.019 Å. The latter sits almost prime to the remainder of the molecule, forming a dihedral angle of 79.14 (9)° with the triazolyl ring. The aldehyde-O1 atom occupies a position anti with respect to the triazolyl-bound methyl group.
Amine-N—H···N(triazoyl) hydrogen bonds feature in the
Table 1, and lead to zigzag chains along the b axis. The chains thus formed are linked into a layer in the ab plane, Fig. 2, by phenyl-C—H···O(aldehyde) and methyl-C—H···O(aldehyde) interactions, indicating the aldehyde-O atom accepts two interactions. The phenyl groups lie to either side of the supramolecular layers that stack along the c axis. However, there are no directional interactions between successive layers.1,2,3-Triazoles derivatives generated in the biological studies (e.g. Jordão et al., 2009) have provided crystals enabling delineation of the dependency of molecular packing patterns upon the
of the substituents, i.e. N-arylamino-1,2,3-triazole (Cunha et al., 2013) and N-(arylamino)-1,2,3-triazole-4-carbohydrazides (Seth et al., 2015).To a solution of oxalyl chloride (3.00 mmol) in anhydrous CH2Cl2 (3.7 mL), maintained under nitrogen at -78 ° C, was added drop wise DMSO (0.42 mL, 6.0 mmol). After stirring for 15 mins, a solution of the precursor alcohol (Cunha et al., 2016; 1.00 mmol) in DMSO (2 mL), followed by anhydrous CH2Cl2 (6.0 mL), were added drop wise. The reaction mixture was maintained at -78 ° C for 90 mins and Me3N (1.05 mL,1.0 mmol) was then added drop wise. After stirring for 20 mins, aqueous NaCl was added, and the organic layer was extracted and concentrated under reduced pressure. The resulting residue was column chromatographed using silica gel and ethyl acetate:hexane (3:7) as νmax (cm-1) 3282 (N—H); 1689 (C═O). 1H NMR (300 MHz, CDCl3): δ 2.57 (s, 3H, CH3), 6.52 (dd, 2H, J = 0.9 and 8.5 Hz, H5 & H9), 7.04 (tt, 1H, J = 0.9 and 7.3 Hz), 7.24-7.30 (m, 2H, H6 and H8), 7.66 (bs, 1H, N–H), 10.2 (s, 1H, CHO). 13C NMR (75 MHz, CDCl3): δ 8.3 (CH3), 113.7 (C5 & C9), 123.1 (C7), 129.5 (C6 & C8), 139.2 (C1 or C2), 142.2 (C1 or C2), 144.7 (C4), 186.0 (CHO). Anal. Calcd. for C10H10N4O: C, 59.40; H, 4.98; N, 27.71. Found: C, 59.38; H, 4.95; N, 27.88.
to give the pure triazole in 80% yield, as a yellow solid; M.pt: 118-120 °C. IR (KBr)The carbon-bound H-atoms were placed in calculated positions (C—H = 0.95–0.98 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C). The nitrogen-bound H-atom was located in a difference Fourier map but were refined with a distance restraint of N—H = 0.88±0.01 Å, and with Uiso(H) set to 1.2Uequiv(N). Owing to poor agreement, a reflection, i.e. (2 1 2), was removed from the final cycles of refinement.To a solution of oxalyl chloride (3.00 mmol) in anhydrous CH2Cl2 (3.7 mL), maintained under nitrogen at -78° C, was added dropwise DMSO (0.42 mL, 6.0 mmol). After stirring for 15 mins, a solution of the precursor alcohol (Cunha et al., 2016; 1.00 mmol) in DMSO (2 mL), followed by anhydrous CH2Cl2 (6.0 mL), were added drop wise. The reaction mixture was maintained at -78° C for 90 mins and Me3N (1.05 mL,1.0 mmol) was then added dropwise. After stirring for 20 mins, aqueous NaCl was added, and the organic layer was extracted and concentrated under reduced pressure. The resulting residue was column chromatographed using silica gel and ethyl acetate:hexane (3:7) as νmax (cm-1) 3282 (N—H); 1689 (C═O). 1H NMR (300 MHz, CDCl3): δ 2.57 (s, 3H, CH3), 6.52 (dd, 2H, J = 0.9 and 8.5 Hz, H5 & H9), 7.04 (tt, 1H, J = 0.9 and 7.3 Hz), 7.24–7.30 (m, 2H, H6 and H8), 7.66 (bs, 1H, N–H), 10.2 (s, 1H, CHO). 13C NMR (75 MHz, CDCl3): δ 8.3 (CH3), 113.7 (C5 & C9), 123.1 (C7), 129.5 (C6 & C8), 139.2 (C1 or C2), 142.2 (C1 or C2), 144.7 (C4), 186.0 (CHO). Anal. calcd. for C10H10N4O: C, 59.40; H, 4.98; N, 27.71. Found: C, 59.38; H, 4.95; N, 27.88.
to give the pure triazole in 80% yield, as a yellow solid; m.p. 118–120°C. IR (KBr)Crystal data, data collection and structure
details are summarized in Table 2. Owing to poor agreement, a reflection, i.e. (2 1 2), was removed from the final cycles of refinement.Interest in 1,2,3-triazoles relates, in part, to their biological activity (Dehaen & Bakulev, 2014). For example, compounds related to the title compound have been evaluated previously for activity against Cantagalo virus (Jordão et al., 2009) and for anti-tubercular activity (Jordão et al., 2011).
The title compound, Fig. 1, comprises two effectively co-planar regions. Thus, the aldehyde group connected at C1 is co-planar with the 1,2,3-triazolyl ring (r.m.s. deviation = 0.007 Å), forming a N4—C1—C10—O1 torsion angle of 3.5 (3)°. Indeed, the r.m.s. deviation of the least-squares plane through all non-hydrogen atoms in the molecule excluding those of the phenyl ring is 0.019 Å. The latter sits almost prime to the remainder of the molecule, forming a dihedral angle of 79.14 (9)° with the triazolyl ring. The aldehyde-O1 atom occupies a position anti with respect to the triazolyl-bound methyl group.
Amine-N—H···N(triazoyl) hydrogen bonds feature in the
Table 1, and lead to supramolecular zigzag chains along the b axis. The chains thus formed are linked into a layer in the ab plane, Fig. 2, by phenyl-C—H···O(aldehyde) and methyl-C—H···O(aldehyde) interactions, indicating the aldehyde-O atom accepts two interactions. The phenyl groups lie to either side of the supramolecular layers that stack along the c axis. However, there are no directional interactions between successive layers.1,2,3-Triazole derivatives generated in the biological studies (e.g. Jordão et al., 2009) have provided crystals enabling delineation of the dependency of molecular packing patterns upon the
of the substituents, i.e. N-arylamino-1,2,3-triazole (Cunha et al., 2013) and N-(arylamino)-1,2,3-triazole-4-carbohydrazides (Seth et al., 2015).Data collection: COLLECT (Hooft, 1998); cell
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. A view of the supramolecular later in the title compound shown in projection down the c axis. The N—H···N and C—H···O interactions are shown as blue and orange dashed lines, respectively. |
C10H10N4O | Dx = 1.336 Mg m−3 |
Mr = 202.22 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, Pbca | Cell parameters from 2601 reflections |
a = 10.2208 (5) Å | θ = 2.9–27.5° |
b = 10.8693 (6) Å | µ = 0.09 mm−1 |
c = 18.1059 (6) Å | T = 120 K |
V = 2011.44 (16) Å3 | Block, colourless |
Z = 8 | 0.42 × 0.36 × 0.14 mm |
F(000) = 848 |
Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer | 2310 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1639 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
φ & ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −14→12 |
Tmin = 0.713, Tmax = 1.000 | l = −16→23 |
15215 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.2474P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.138 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2310 reflections | Δρmin = −0.25 e Å−3 |
141 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2014), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.008 (2) |
C10H10N4O | V = 2011.44 (16) Å3 |
Mr = 202.22 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.2208 (5) Å | µ = 0.09 mm−1 |
b = 10.8693 (6) Å | T = 120 K |
c = 18.1059 (6) Å | 0.42 × 0.36 × 0.14 mm |
Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer | 2310 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1639 reflections with I > 2σ(I) |
Tmin = 0.713, Tmax = 1.000 | Rint = 0.056 |
15215 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2310 reflections | Δρmin = −0.25 e Å−3 |
141 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.79842 (12) | 0.40421 (12) | 0.54426 (7) | 0.0402 (4) | |
N1 | 0.91541 (13) | 0.88492 (13) | 0.41939 (7) | 0.0247 (3) | |
H1N | 0.8472 (13) | 0.9349 (14) | 0.4211 (10) | 0.030* | |
N2 | 0.88217 (12) | 0.76712 (12) | 0.44112 (7) | 0.0219 (3) | |
N3 | 0.81206 (12) | 0.69078 (13) | 0.39631 (7) | 0.0248 (3) | |
N4 | 0.79436 (12) | 0.58967 (13) | 0.43324 (7) | 0.0238 (3) | |
C1 | 0.85041 (15) | 0.60189 (15) | 0.50173 (8) | 0.0229 (4) | |
C2 | 0.90728 (15) | 0.71584 (15) | 0.50683 (8) | 0.0233 (4) | |
C3 | 0.98009 (17) | 0.77895 (18) | 0.56623 (9) | 0.0348 (5) | |
H3A | 1.0446 | 0.8348 | 0.5444 | 0.052* | |
H3B | 1.0250 | 0.7178 | 0.5969 | 0.052* | |
H3C | 0.9189 | 0.8261 | 0.5968 | 0.052* | |
C4 | 0.99103 (15) | 0.89324 (15) | 0.35369 (8) | 0.0227 (4) | |
C5 | 1.08721 (16) | 0.80734 (16) | 0.33814 (9) | 0.0287 (4) | |
H5 | 1.1020 | 0.7401 | 0.3706 | 0.034* | |
C6 | 1.16142 (17) | 0.82057 (18) | 0.27480 (10) | 0.0344 (5) | |
H6 | 1.2264 | 0.7611 | 0.2633 | 0.041* | |
C7 | 1.14220 (17) | 0.91920 (18) | 0.22815 (10) | 0.0347 (5) | |
H7 | 1.1929 | 0.9271 | 0.1844 | 0.042* | |
C8 | 1.04906 (16) | 1.00614 (17) | 0.24536 (9) | 0.0311 (4) | |
H8 | 1.0377 | 1.0756 | 0.2142 | 0.037* | |
C9 | 0.97184 (15) | 0.99312 (15) | 0.30771 (9) | 0.0259 (4) | |
H9 | 0.9063 | 1.0523 | 0.3188 | 0.031* | |
C10 | 0.84565 (17) | 0.50441 (17) | 0.55572 (10) | 0.0315 (4) | |
H10 | 0.8818 | 0.5199 | 0.6032 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0422 (8) | 0.0268 (8) | 0.0518 (9) | −0.0059 (6) | −0.0096 (6) | 0.0107 (6) |
N1 | 0.0283 (7) | 0.0169 (7) | 0.0289 (7) | 0.0013 (6) | 0.0038 (6) | 0.0016 (6) |
N2 | 0.0249 (7) | 0.0178 (7) | 0.0231 (7) | −0.0021 (6) | 0.0009 (5) | −0.0018 (5) |
N3 | 0.0271 (7) | 0.0229 (8) | 0.0246 (7) | −0.0037 (6) | −0.0002 (5) | −0.0033 (6) |
N4 | 0.0253 (7) | 0.0211 (8) | 0.0250 (7) | −0.0009 (6) | 0.0003 (5) | −0.0014 (6) |
C1 | 0.0209 (8) | 0.0225 (9) | 0.0251 (9) | 0.0000 (6) | −0.0016 (6) | 0.0001 (6) |
C2 | 0.0230 (8) | 0.0226 (9) | 0.0242 (8) | 0.0014 (7) | −0.0019 (6) | 0.0013 (6) |
C3 | 0.0390 (10) | 0.0330 (11) | 0.0325 (10) | −0.0082 (8) | −0.0130 (7) | 0.0001 (8) |
C4 | 0.0246 (8) | 0.0210 (9) | 0.0224 (8) | −0.0042 (7) | −0.0014 (6) | −0.0011 (6) |
C5 | 0.0274 (8) | 0.0259 (10) | 0.0328 (9) | 0.0004 (7) | 0.0014 (7) | 0.0034 (7) |
C6 | 0.0273 (9) | 0.0358 (12) | 0.0401 (11) | 0.0027 (8) | 0.0073 (7) | −0.0010 (8) |
C7 | 0.0325 (10) | 0.0409 (12) | 0.0306 (10) | −0.0068 (8) | 0.0076 (7) | 0.0025 (8) |
C8 | 0.0351 (9) | 0.0292 (10) | 0.0289 (9) | −0.0075 (7) | −0.0009 (7) | 0.0061 (7) |
C9 | 0.0274 (8) | 0.0223 (9) | 0.0282 (9) | −0.0019 (7) | −0.0018 (7) | −0.0009 (7) |
C10 | 0.0310 (9) | 0.0273 (10) | 0.0363 (10) | −0.0017 (8) | −0.0078 (7) | 0.0044 (8) |
O1—C10 | 1.209 (2) | C3—H3C | 0.9800 |
N1—N2 | 1.3818 (18) | C4—C9 | 1.382 (2) |
N1—C4 | 1.421 (2) | C4—C5 | 1.385 (2) |
N1—H1N | 0.885 (9) | C5—C6 | 1.383 (2) |
N2—C2 | 1.3387 (19) | C5—H5 | 0.9500 |
N2—N3 | 1.3639 (17) | C6—C7 | 1.379 (3) |
N3—N4 | 1.2990 (18) | C6—H6 | 0.9500 |
N4—C1 | 1.372 (2) | C7—C8 | 1.377 (3) |
C1—C2 | 1.371 (2) | C7—H7 | 0.9500 |
C1—C10 | 1.442 (2) | C8—C9 | 1.385 (2) |
C2—C3 | 1.477 (2) | C8—H8 | 0.9500 |
C3—H3A | 0.9800 | C9—H9 | 0.9500 |
C3—H3B | 0.9800 | C10—H10 | 0.9500 |
N2—N1—C4 | 115.52 (13) | C9—C4—N1 | 118.49 (14) |
N2—N1—H1N | 111.4 (12) | C5—C4—N1 | 120.88 (14) |
C4—N1—H1N | 114.8 (12) | C6—C5—C4 | 119.21 (16) |
C2—N2—N3 | 112.09 (13) | C6—C5—H5 | 120.4 |
C2—N2—N1 | 126.28 (13) | C4—C5—H5 | 120.4 |
N3—N2—N1 | 121.57 (12) | C7—C6—C5 | 120.72 (17) |
N4—N3—N2 | 106.36 (12) | C7—C6—H6 | 119.6 |
N3—N4—C1 | 108.97 (13) | C5—C6—H6 | 119.6 |
C2—C1—N4 | 108.98 (14) | C8—C7—C6 | 119.56 (16) |
C2—C1—C10 | 129.21 (15) | C8—C7—H7 | 120.2 |
N4—C1—C10 | 121.81 (15) | C6—C7—H7 | 120.2 |
N2—C2—C1 | 103.59 (13) | C7—C8—C9 | 120.55 (16) |
N2—C2—C3 | 123.40 (15) | C7—C8—H8 | 119.7 |
C1—C2—C3 | 133.01 (15) | C9—C8—H8 | 119.7 |
C2—C3—H3A | 109.5 | C4—C9—C8 | 119.38 (16) |
C2—C3—H3B | 109.5 | C4—C9—H9 | 120.3 |
H3A—C3—H3B | 109.5 | C8—C9—H9 | 120.3 |
C2—C3—H3C | 109.5 | O1—C10—C1 | 123.98 (16) |
H3A—C3—H3C | 109.5 | O1—C10—H10 | 118.0 |
H3B—C3—H3C | 109.5 | C1—C10—H10 | 118.0 |
C9—C4—C5 | 120.52 (15) | ||
C4—N1—N2—C2 | 124.41 (16) | C10—C1—C2—C3 | −0.6 (3) |
C4—N1—N2—N3 | −58.74 (18) | N2—N1—C4—C9 | 146.17 (14) |
C2—N2—N3—N4 | −1.04 (17) | N2—N1—C4—C5 | −37.6 (2) |
N1—N2—N3—N4 | −178.30 (12) | C9—C4—C5—C6 | −1.9 (2) |
N2—N3—N4—C1 | 1.16 (16) | N1—C4—C5—C6 | −178.06 (15) |
N3—N4—C1—C2 | −0.93 (17) | C4—C5—C6—C7 | 1.3 (3) |
N3—N4—C1—C10 | 179.48 (15) | C5—C6—C7—C8 | 0.8 (3) |
N3—N2—C2—C1 | 0.45 (17) | C6—C7—C8—C9 | −2.1 (3) |
N1—N2—C2—C1 | 177.56 (14) | C5—C4—C9—C8 | 0.6 (2) |
N3—N2—C2—C3 | −179.19 (15) | N1—C4—C9—C8 | 176.79 (14) |
N1—N2—C2—C3 | −2.1 (2) | C7—C8—C9—C4 | 1.5 (3) |
N4—C1—C2—N2 | 0.27 (17) | C2—C1—C10—O1 | −176.00 (18) |
C10—C1—C2—N2 | 179.83 (16) | N4—C1—C10—O1 | 3.5 (3) |
N4—C1—C2—C3 | 179.87 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N4i | 0.89 (2) | 2.23 (2) | 3.101 (2) | 168 (1) |
C3—H3C···O1i | 0.98 | 2.56 | 3.181 (2) | 121 |
C5—H5···O1ii | 0.95 | 2.42 | 3.345 (2) | 163 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N4i | 0.885 (15) | 2.230 (15) | 3.101 (2) | 167.8 (13) |
C3—H3C···O1i | 0.98 | 2.56 | 3.181 (2) | 121 |
C5—H5···O1ii | 0.95 | 2.42 | 3.345 (2) | 163 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H10N4O |
Mr | 202.22 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 120 |
a, b, c (Å) | 10.2208 (5), 10.8693 (6), 18.1059 (6) |
V (Å3) | 2011.44 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.36 × 0.14 |
Data collection | |
Diffractometer | Bruker–Nonius 95mm CCD camera on κ-goniostat |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.713, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15215, 2310, 1639 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.138, 1.05 |
No. of reflections | 2310 |
No. of parameters | 141 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.25 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Footnotes
‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
Acknowledgements
This work was supported by the Brazilian agency FAPERJ. Fellowships granted to Universidade Federal Fluminense by FAPERJ, CAPES and CNPq–PIBIC are gratefully acknowledged.
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