organic compounds
[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol
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, UK, 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
In the title compound, C10H10Cl2N4O, the hydroxy group and benzene ring are disposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral angle between the five- and six-membered rings is 87.51 (12)°, and the C—O bond of the hydroxy group lies almost normal to the plane of the 5-membered ring [N—C—C—O = −93.2 (2)°]. An intramolecular amino-N—H⋯Cl hydrogen bond is noted. In the extended structure, supramolecular layers in the ab plane are formed via hydroxy-O—H⋯N(ring) and amine-N—H⋯O(hydroxy) hydrogen bonds. The layers are connected along the c axis by π–π contacts between benzene rings [inter-centroid distance = 3.7789 (13) Å] and by C—Cl⋯π interactions.
Keywords: crystal structure; 1,2,3-triazolyl; alcohol; hydrogen bonding.
CCDC reference: 672063
Structure description
1,2,3-Triazole derivatives attract continuing interest as a result of their biological activities (Dehaen & Bakulev, 2014). Diseases that have been evaluated recently include tuberculosis (Jordão et al., 2011), and the susceptibility of Cantagalo virus to 1,2,3-triazoles has also been investigated (Jordão et al., 2009). These studies have provided a number of crystals enabling systematic studies of the influence of the of aryl-bound substituents upon crystal packing patterns (Cunha et al., 2013; Seth et al., 2015).
The central 1,2,3-triazolyl ring (r.m.s. deviation = 0.006 Å) in the title compound, Fig. 1, is flanked by C1-bound hydroxymethyl and N2-bound amino-2,5-dichlorobenzene substituents which lie to opposite sides of the ring. The C—O grouping of the hydroxyl group lies almost normal to the ring with the N4—C1—C10—O1 torsion angle being −93.2 (2)°. The dihedral angle between the triazolyl and benzene rings is 87.51 (12)°, with the latter being almost perpendicular, forming a N2—N1—C4—C5 torsion angle of −8.9 (3)°. This alignment allows for the formation of an intramolecular amino-N—H⋯Cl hydrogen bond, Table 1.
In the molecular packing, the hydroxy group is pivotal in the hydrogen-bonding scheme, forming donor hydroxy-O—H⋯N(ring) and acceptor amine-N—H⋯O(hydroxy) interactions, Table 1. The latter interactions assemble molecules into dimers and these are in turn connected into supramolecular layers in the ab plane by the former interactions. The connections between layers are afforded by inter-digitating benzene rings via π—π contacts [inter-centroid distance = 3.7789 (13) Å for 1 − x, − + y, − z] and C—Cl⋯π interactions, Table 1 and Fig. 2.
Synthesis and crystallization
A solution of the desired 4-carbethoxy-triazole (Cunha et al., 2013) (1.00 mmol) in anhydrous THF (5 ml) was added dropwise to a suspension of LiAlH4 (2 mmol) in anhydrous THF (10 ml) under a nitrogen atmosphere at 0°C. The reaction mixture was stirred at room temperature for 2 h, water (10 ml) was added, the aqueous layer acidified to pH 1 with 1 M HCl, and extracted with CH2Cl2 (3 ×). The organic extracts were combined, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was washed with hexane/dichloromethane (3:1) and dried under vacuum. 44% yield. Crystals were obtained from the slow evaporation of its methanol solution. M.p. 197°C. IR (KBr) νmax (cm−1): 3184 (N—H); 3096 (O—H). 1H NMR (300 MHz, DMSO-d6) δ: 2.18 (s, 3H, CH3), 4.55 (d, 2H, J = 5.6 Hz, CH2OH), 5.19 (t, 1H, J = 5.6 Hz, CH2OH), 5.80 (d, 1H, J = 2.4 Hz, H5), 7.00 (dd, 1H, J = 2.4 & 8.5 Hz, H7), 7.50 (d, 1H, J = 8.5 Hz, H8), 10.21 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6) δ: 6.8 (CH3), 54.8 (CH2), 112.4 (C5), 116.4 (C6), 121.5 (C7), 131.3 (C8), 132.0 (C9), 132.7 (C1or C2), 143.6 (C1 or C2), 143.7 (C4). Anal. calcd. For C10H10Cl2N4O: C, 43.98; H, 3.69; N, 20.51. Found: C, 44.01; H, 3.72; N, 20.09.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 672063
10.1107/S2414314615024475/hb4004sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314615024475/hb4004Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314615024475/hb4004Isup3.cml
1,2,3-Triazoles derivatives attract continuing interest as a result of their biological activities (Dehaen & Bakulev, 2014). Diseases that have been evaluated recently include tuberculosis (Jordão et al., 2011), and the susceptibility of Cantagalo virus to 1,2,3-triazoles has also been investigated (Jordão et al., 2009). These studies have provided a number of crystals enabling systematic studies of the influence of the
of aryl-bound substituents upon crystal packing patterns (Cunha et al., 2013; Seth et al., 2015).The central 1,2,3-triazolyl ring (r.m.s. deviation = 0.006 Å) in the title compound, Fig. 1, is flanked by C1-bound hydroxymethyl and N2-bound amino-2,5-dichlorobenzene substituents which lie to opposite sides of the ring. The hydroxyl group lie almost normal to the ring with the N4—C1—C10—O1 torsion angle being -93.2 (2)°. The dihedral angle between the triazolyl and benzene rings is 87.51 (12)°, with the latter being almost perpendicular, forming a N2—N1—C4—C5 torsion angle of -8.9 (3)°. This alignment allows for the formation of an intramolecular amino-N—H···Cl hydrogen bond, Table 1.
In the molecular packing, the hydroxy group is pivotal in the hydrogen bonding scheme, forming donor hydroxy-O—H···N(ring) and acceptor amine-N—H···O(hydroxy) interactions, Table 1. The latter interactions assemble molecules into dimers and these are in turn connected into supramolecular layers in the ab plane by the former interactions. The connections between layers are afforded by inter-digitating benzene rings via π—π contacts (inter-centroid distance = 3.7789 (13) Å for 1-x, -1/2+y, 3/2-z) and C—Cl···π interactions, Table 1 and Fig. 2.
A solution of the desired 4-carbethoxy-triazole (Cunha et al., 2013) (1.00 mmol) in anhydrous THF (5 ml) was added drop-wise to a suspension of LiAlH4 (2 mmol) in anhydrous THF (10 ml) under a nitrogen atmosphere at 0°C. The reaction mixture was stirred at room temperature for 2 h, water (10 ml) was added, the aqueous layer acidified to pH 1 with 1 M HCl, and extracted with CHCl2 (3 ×). The organic extracts were combined, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was washed with hexane/dichloromethane (3:1) and dried under vacuum. 44% yield. Crystals were obtained from the slow evaporation of its methanol solution. M.pt: 197 °C. IR (KBr) νmax (cm-1): 3184 (N—H); 3096 (O—H). 1H NMR (300 MHz, DMSO-d6) δ: 2.18 (s, 3H, CH3), 4.55 (d, 2H, J = 5.6 Hz, CH2OH), 5.19 (t, 1H, J = 5.6 Hz, CH2OH), 5.80 (d, 1H, J = 2.4 Hz, H5), 7.00 (dd, 1H, J = 2.4 & 8.5 Hz, H7), 7.50 (d, 1H, J = 8.5 Hz, H8), 10.21 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6) δ: 6.8 (CH3), 54.8 (CH2), 112.4 (C5), 116.4 (C6), 121.5 (C7), 131.3 (C8), 132.0 (C9), 132.7 (C1or C2), 143.6 (C1 or C2), 143.7 (C4). Anal. Calcd. For C10H10Cl2N4O: C, 43.98; H, 3.69; N, 20.51. Found: C, 44.01; H, 3.72; N, 20.09.
The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.98 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C). The oxygen and nitrogen-bound H-atoms were located in a difference Fourier map but were refined with a distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, and with Uiso(H) set to 1.5Uequiv(O) or 1.2Uequiv(N).A solution of the desired 4-carbethoxy-triazole (Cunha et al., 2013) (1.00 mmol) in anhydrous THF (5 ml) was added dropwise to a suspension of LiAlH4 (2 mmol) in anhydrous THF (10 ml) under a nitrogen atmosphere at 0°C. The reaction mixture was stirred at room temperature for 2 h, water (10 ml) was added, the aqueous layer acidified to pH 1 with 1 M HCl, and extracted with CHCl2 (3 ×). The organic extracts were combined, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was washed with hexane/dichloromethane (3:1) and dried under vacuum. 44% yield. Crystals were obtained from the slow evaporation of its methanol solution. M.p. 197°C. IR (KBr) νmax (cm-1): 3184 (N—H); 3096 (O—H). 1H NMR (300 MHz, DMSO-d6) δ: 2.18 (s, 3H, CH3), 4.55 (d, 2H, J = 5.6 Hz, CH2OH), 5.19 (t, 1H, J = 5.6 Hz, CH2OH), 5.80 (d, 1H, J = 2.4 Hz, H5), 7.00 (dd, 1H, J = 2.4 & 8.5 Hz, H7), 7.50 (d, 1H, J = 8.5 Hz, H8), 10.21 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6) δ: 6.8 (CH3), 54.8 (CH2), 112.4 (C5), 116.4 (C6), 121.5 (C7), 131.3 (C8), 132.0 (C9), 132.7 (C1or C2), 143.6 (C1 or C2), 143.7 (C4). Anal. calcd. For C10H10Cl2N4O: C, 43.98; H, 3.69; N, 20.51. Found: C, 44.01; H, 3.72; N, 20.09.
1,2,3-Triazoles derivatives attract continuing interest as a result of their biological activities (Dehaen & Bakulev, 2014). Diseases that have been evaluated recently include tuberculosis (Jordão et al., 2011), and the susceptibility of Cantagalo virus to 1,2,3-triazoles has also been investigated (Jordão et al., 2009). These studies have provided a number of crystals enabling systematic studies of the influence of the
of aryl-bound substituents upon crystal packing patterns (Cunha et al., 2013; Seth et al., 2015).The central 1,2,3-triazolyl ring (r.m.s. deviation = 0.006 Å) in the title compound, Fig. 1, is flanked by C1-bound hydroxymethyl and N2-bound amino-2,5-dichlorobenzene substituents which lie to opposite sides of the ring. The C—O grouping of the hydroxyl group lies almost normal to the ring with the N4—C1—C10—O1 torsion angle being -93.2 (2)°. The dihedral angle between the triazolyl and benzene rings is 87.51 (12)°, with the latter being almost perpendicular, forming a N2—N1—C4—C5 torsion angle of -8.9 (3)°. This alignment allows for the formation of an intramolecular amino-N—H···Cl hydrogen bond, Table 1.
In the molecular packing, the hydroxy group is pivotal in the hydrogen-bonding scheme, forming donor hydroxy-O—H···N(ring) and acceptor amine-N—H···O(hydroxy) interactions, Table 1. The latter interactions assemble molecules into dimers and these are in turn connected into supramolecular layers in the ab plane by the former interactions. The connections between layers are afforded by inter-digitating benzene rings via π—π contacts [inter-centroid distance = 3.7789 (13) Å for 1 - x, -1/2 + y, 3/2 - z] and C—Cl···π interactions, Table 1 and Fig. 2.
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) and 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 unit cell contents of the title compound shown in projection down the b axis. The O—H···O, N—H···O, π—π and C—Cl···π interactions are shown as orange, blue, green and brown dashed lines, respectively. |
C10H10Cl2N4O | F(000) = 560 |
Mr = 273.12 | Dx = 1.572 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 12.1802 (5) Å | Cell parameters from 2686 reflections |
b = 7.3646 (4) Å | θ = 2.9–27.5° |
c = 13.9001 (8) Å | µ = 0.55 mm−1 |
β = 112.276 (3)° | T = 120 K |
V = 1153.81 (11) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.18 × 0.16 mm |
Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer | 2645 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
φ & ω scans | h = −15→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −9→9 |
Tmin = 0.768, Tmax = 1.000 | l = −18→17 |
12461 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.5445P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.117 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.33 e Å−3 |
2645 reflections | Δρmin = −0.40 e Å−3 |
161 parameters |
C10H10Cl2N4O | V = 1153.81 (11) Å3 |
Mr = 273.12 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1802 (5) Å | µ = 0.55 mm−1 |
b = 7.3646 (4) Å | T = 120 K |
c = 13.9001 (8) Å | 0.26 × 0.18 × 0.16 mm |
β = 112.276 (3)° |
Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer | 2645 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1963 reflections with I > 2σ(I) |
Tmin = 0.768, Tmax = 1.000 | Rint = 0.062 |
12461 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 161 parameters |
wR(F2) = 0.117 | 2 restraints |
S = 1.06 | Δρmax = 0.33 e Å−3 |
2645 reflections | Δρmin = −0.40 e Å−3 |
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 | ||
Cl1 | 0.37932 (5) | 0.38765 (8) | 0.87969 (5) | 0.02943 (19) | |
Cl2 | 0.68215 (5) | 0.39438 (8) | 0.60698 (4) | 0.02549 (18) | |
O1 | 1.07381 (14) | 0.3879 (2) | 1.25648 (13) | 0.0289 (4) | |
H1O | 1.098 (2) | 0.319 (3) | 1.3086 (16) | 0.043* | |
N1 | 0.78023 (15) | 0.4396 (3) | 0.83509 (14) | 0.0188 (4) | |
H1N | 0.8125 (19) | 0.503 (3) | 0.8004 (17) | 0.023* | |
N2 | 0.82967 (15) | 0.4789 (2) | 0.94015 (13) | 0.0163 (4) | |
N3 | 0.83152 (15) | 0.6498 (2) | 0.97786 (14) | 0.0190 (4) | |
N4 | 0.87624 (15) | 0.6334 (2) | 1.07929 (14) | 0.0190 (4) | |
C1 | 0.90092 (17) | 0.4551 (3) | 1.10644 (16) | 0.0177 (5) | |
C2 | 0.87186 (17) | 0.3534 (3) | 1.01696 (17) | 0.0175 (5) | |
C3 | 0.8799 (2) | 0.1582 (3) | 0.99578 (19) | 0.0249 (5) | |
H3A | 0.8016 | 0.1136 | 0.9502 | 0.037* | |
H3B | 0.9070 | 0.0906 | 1.0614 | 0.037* | |
H3C | 0.9364 | 0.1410 | 0.9617 | 0.037* | |
C4 | 0.65537 (18) | 0.4209 (3) | 0.79153 (16) | 0.0164 (4) | |
C5 | 0.58710 (19) | 0.4161 (3) | 0.85238 (17) | 0.0190 (5) | |
H5 | 0.6234 | 0.4282 | 0.9258 | 0.023* | |
C6 | 0.46531 (19) | 0.3934 (3) | 0.80412 (18) | 0.0195 (5) | |
C7 | 0.40899 (19) | 0.3747 (3) | 0.69811 (18) | 0.0227 (5) | |
H7 | 0.3252 | 0.3615 | 0.6670 | 0.027* | |
C8 | 0.4772 (2) | 0.3757 (3) | 0.63790 (18) | 0.0231 (5) | |
H8 | 0.4404 | 0.3614 | 0.5647 | 0.028* | |
C9 | 0.59873 (19) | 0.3976 (3) | 0.68423 (17) | 0.0185 (5) | |
C10 | 0.94792 (19) | 0.3937 (3) | 1.21697 (17) | 0.0211 (5) | |
H10A | 0.9215 | 0.4782 | 1.2592 | 0.025* | |
H10B | 0.9164 | 0.2715 | 1.2216 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0241 (3) | 0.0385 (4) | 0.0300 (4) | −0.0026 (2) | 0.0151 (3) | −0.0009 (3) |
Cl2 | 0.0269 (3) | 0.0356 (4) | 0.0139 (3) | 0.0017 (2) | 0.0077 (2) | −0.0017 (2) |
O1 | 0.0178 (8) | 0.0412 (11) | 0.0218 (9) | −0.0036 (7) | 0.0011 (7) | 0.0160 (7) |
N1 | 0.0197 (9) | 0.0277 (10) | 0.0083 (9) | −0.0043 (7) | 0.0045 (7) | −0.0016 (7) |
N2 | 0.0177 (8) | 0.0190 (10) | 0.0111 (9) | −0.0001 (7) | 0.0041 (7) | −0.0008 (7) |
N3 | 0.0193 (9) | 0.0213 (10) | 0.0143 (10) | −0.0011 (7) | 0.0038 (7) | −0.0008 (7) |
N4 | 0.0195 (9) | 0.0230 (10) | 0.0128 (10) | −0.0006 (7) | 0.0043 (7) | −0.0009 (7) |
C1 | 0.0149 (10) | 0.0225 (11) | 0.0155 (11) | −0.0018 (8) | 0.0055 (8) | 0.0003 (9) |
C2 | 0.0147 (10) | 0.0228 (12) | 0.0151 (11) | −0.0004 (8) | 0.0060 (8) | 0.0020 (9) |
C3 | 0.0324 (13) | 0.0213 (12) | 0.0226 (13) | 0.0030 (9) | 0.0122 (10) | 0.0026 (10) |
C4 | 0.0161 (10) | 0.0163 (10) | 0.0142 (11) | 0.0004 (8) | 0.0030 (8) | 0.0005 (8) |
C5 | 0.0211 (11) | 0.0224 (12) | 0.0114 (11) | −0.0003 (8) | 0.0037 (9) | −0.0013 (8) |
C6 | 0.0193 (11) | 0.0182 (11) | 0.0224 (12) | −0.0003 (8) | 0.0095 (9) | −0.0004 (9) |
C7 | 0.0170 (11) | 0.0217 (12) | 0.0242 (13) | −0.0011 (8) | 0.0020 (9) | −0.0015 (9) |
C8 | 0.0248 (12) | 0.0238 (12) | 0.0143 (11) | 0.0000 (9) | 0.0002 (9) | −0.0013 (9) |
C9 | 0.0232 (11) | 0.0176 (11) | 0.0146 (11) | 0.0014 (8) | 0.0070 (9) | −0.0002 (8) |
C10 | 0.0201 (11) | 0.0281 (13) | 0.0140 (11) | −0.0008 (9) | 0.0055 (9) | 0.0014 (9) |
Cl1—C6 | 1.742 (2) | C3—H3A | 0.9800 |
Cl2—C9 | 1.736 (2) | C3—H3B | 0.9800 |
O1—C10 | 1.420 (3) | C3—H3C | 0.9800 |
O1—H1O | 0.839 (10) | C4—C5 | 1.393 (3) |
N1—N2 | 1.383 (2) | C4—C9 | 1.396 (3) |
N1—C4 | 1.414 (3) | C5—C6 | 1.387 (3) |
N1—H1N | 0.866 (10) | C5—H5 | 0.9500 |
N2—C2 | 1.357 (3) | C6—C7 | 1.376 (3) |
N2—N3 | 1.361 (3) | C7—C8 | 1.385 (3) |
N3—N4 | 1.310 (3) | C7—H7 | 0.9500 |
N4—C1 | 1.368 (3) | C8—C9 | 1.382 (3) |
C1—C2 | 1.378 (3) | C8—H8 | 0.9500 |
C1—C10 | 1.492 (3) | C10—H10A | 0.9900 |
C2—C3 | 1.478 (3) | C10—H10B | 0.9900 |
C10—O1—H1O | 109 (2) | C9—C4—N1 | 119.01 (18) |
N2—N1—C4 | 116.08 (16) | C6—C5—C4 | 119.0 (2) |
N2—N1—H1N | 111.5 (16) | C6—C5—H5 | 120.5 |
C4—N1—H1N | 117.1 (16) | C4—C5—H5 | 120.5 |
C2—N2—N3 | 112.40 (17) | C7—C6—C5 | 122.5 (2) |
C2—N2—N1 | 124.87 (18) | C7—C6—Cl1 | 118.26 (16) |
N3—N2—N1 | 122.50 (17) | C5—C6—Cl1 | 119.24 (17) |
N4—N3—N2 | 105.56 (16) | C6—C7—C8 | 118.48 (19) |
N3—N4—C1 | 110.12 (17) | C6—C7—H7 | 120.8 |
N4—C1—C2 | 108.56 (19) | C8—C7—H7 | 120.8 |
N4—C1—C10 | 122.24 (19) | C9—C8—C7 | 120.1 (2) |
C2—C1—C10 | 129.2 (2) | C9—C8—H8 | 120.0 |
N2—C2—C1 | 103.36 (18) | C7—C8—H8 | 120.0 |
N2—C2—C3 | 122.65 (19) | C8—C9—C4 | 121.3 (2) |
C1—C2—C3 | 134.0 (2) | C8—C9—Cl2 | 119.02 (17) |
C2—C3—H3A | 109.5 | C4—C9—Cl2 | 119.63 (16) |
C2—C3—H3B | 109.5 | O1—C10—C1 | 110.11 (17) |
H3A—C3—H3B | 109.5 | O1—C10—H10A | 109.6 |
C2—C3—H3C | 109.5 | C1—C10—H10A | 109.6 |
H3A—C3—H3C | 109.5 | O1—C10—H10B | 109.6 |
H3B—C3—H3C | 109.5 | C1—C10—H10B | 109.6 |
C5—C4—C9 | 118.58 (19) | H10A—C10—H10B | 108.2 |
C5—C4—N1 | 122.34 (19) | ||
C4—N1—N2—C2 | 93.4 (2) | N2—N1—C4—C9 | 174.27 (18) |
C4—N1—N2—N3 | −80.6 (2) | C9—C4—C5—C6 | −1.7 (3) |
C2—N2—N3—N4 | 0.6 (2) | N1—C4—C5—C6 | −178.6 (2) |
N1—N2—N3—N4 | 175.36 (16) | C4—C5—C6—C7 | 0.2 (3) |
N2—N3—N4—C1 | −1.0 (2) | C4—C5—C6—Cl1 | −179.89 (16) |
N3—N4—C1—C2 | 1.0 (2) | C5—C6—C7—C8 | 1.1 (3) |
N3—N4—C1—C10 | −177.30 (18) | Cl1—C6—C7—C8 | −178.78 (17) |
N3—N2—C2—C1 | 0.0 (2) | C6—C7—C8—C9 | −0.9 (3) |
N1—N2—C2—C1 | −174.61 (17) | C7—C8—C9—C4 | −0.7 (3) |
N3—N2—C2—C3 | −179.43 (18) | C7—C8—C9—Cl2 | 178.92 (17) |
N1—N2—C2—C3 | 6.0 (3) | C5—C4—C9—C8 | 2.0 (3) |
N4—C1—C2—N2 | −0.6 (2) | N1—C4—C9—C8 | 178.94 (19) |
C10—C1—C2—N2 | 177.57 (19) | C5—C4—C9—Cl2 | −177.60 (16) |
N4—C1—C2—C3 | 178.7 (2) | N1—C4—C9—Cl2 | −0.6 (3) |
C10—C1—C2—C3 | −3.1 (4) | N4—C1—C10—O1 | −93.2 (2) |
N2—N1—C4—C5 | −8.9 (3) | C2—C1—C10—O1 | 88.9 (3) |
Cg1 is the centroid of the C4–C9 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl2 | 0.87 (2) | 2.67 (2) | 2.9530 (19) | 100 (2) |
O1—H1O···N4i | 0.84 (2) | 2.01 (2) | 2.836 (2) | 169 (2) |
N1—H1N···O1ii | 0.87 (2) | 2.01 (2) | 2.848 (3) | 165 (2) |
C6—Cl1···Cg1iii | 1.74 (1) | 3.73 (1) | 5.411 (3) | 161 (1) |
Symmetry codes: (i) −x+2, y−1/2, −z+5/2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+2. |
Cg1 is the centroid of the C4–C9 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl2 | 0.87 (2) | 2.67 (2) | 2.9530 (19) | 100.2 (17) |
O1—H1O···N4i | 0.84 (2) | 2.01 (2) | 2.836 (2) | 169 (2) |
N1—H1N···O1ii | 0.87 (2) | 2.01 (2) | 2.848 (3) | 165 (2) |
C6—Cl1···Cg1iii | 1.742 (2) | 3.7326 (12) | 5.411 (3) | 161.12 (8) |
Symmetry codes: (i) −x+2, y−1/2, −z+5/2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C10H10Cl2N4O |
Mr | 273.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 12.1802 (5), 7.3646 (4), 13.9001 (8) |
β (°) | 112.276 (3) |
V (Å3) | 1153.81 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.26 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker-Nonius 95mm CCD camera on κ-goniostat |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.768, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12461, 2645, 1963 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.117, 1.06 |
No. of reflections | 2645 |
No. of parameters | 161 |
No. of restraints | 2 |
Δρmax, Δρmin (e Å−3) | 0.33, −0.40 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and 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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