research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 2| February 2015| Pages 188-191

Crystal structure of 2-(2-amino­phen­yl)-1,3-benzoxazole

aÁrea Académica de Química, Universidad Autónoma del Estado de Hidalgo, km. 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo CP 42184, Mexico, and bCentro Conjunto de Investigación en Química Sustentable, UAEM-UNAM, carretera Toluca-Atlacomulco km. 14.5, CP 50200, Toluca, Estado de México, Mexico
*Correspondence e-mail: mei_781@hotmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 November 2014; accepted 9 January 2015; online 21 January 2015)

Crystals of the title compound, C13H10N2O, were grown from a di­chloro­methane/ketone/methanol solvent mixture. It crystallizes with two mol­ecules, A and B, in the asymmetric unit with very similar almost planar conformations [dihedral angles between the ring planes = 0.74 (8) and 0.67 (6)° for mol­ecules A and B, respectively; r.m.s. overlay fit = 0.019 Å]. Each mol­ecule features an intra­molecular N—H⋯N hydrogen bond, which closes an S(6) ring and therefore establishes a syn relationship for the N atoms. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds, generating [100] chains containing alternating A and B mol­ecules. Weak aromatic ππ stacking [minimum centroid–centroid separation = 3.6212 (9) Å] links the chains into a three-dimensional network.

1. Chemical context

Benzimidazole, benzoxazole, and benzo­thia­zole derivatives are key components in many bioactive compounds of both natural and synthetic origin; many are active components of biocides such as bactericides, fungicides, insecticides and anti­carcinogens (Kumar-Samota & Seth, 2010[Kumar-Samota, M. & Seth, G. (2010). Heteroatom Chem. 21, 44-50.]). Benzoxazole derivatives have been used as building blocks for biochemical and pharmaceutical agents, as well as dyes, fluorescent brightening agents, biomarkers and biosensors (Costa et al. 2007[Costa, S. P. G., Oliveira, E., Lodeiro, C. & Raposo, M. M. M. (2007). Sensors, 7, 2096-29114.] and Tong et al. 2005[Tong, Y. P., Zheng, S. L. & Chen, X. M. (2005). Inorg. Chem. 44, 4270-4275.]).

[Scheme 1]

In this context, 2-(2-amino­phen­yl)benzoxazole has shown considerable growth inhibition with respect to fungi and gram-positive and gram-negative bacteria (Elnima et al. 1981[Elnima, E. I., Zubair, M. U. & Al-Badr, A. A. (1981). Antimicrob. Agents Chemother. 19, 29-32.]). For this reason, several methods have been described for the synthesis of these heterocyclic compounds, some of which are summarized in the Scheme, which shows the retrosynthesis for the preparation of the title compound, (I)[link]. For example, Gajare et al. (2000[Gajare, A. S., Shaikh, N. S., Jnaneshwara, G. K., Deshpande, V. H., Ravindranathan, T. & Bedekar, A. V. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 999-1001.]) described a procedure for the preparation of 2-(o-amino­phen­yl)oxazolines from isatoic anhydride and 2-amino­alcohols at reflux of PhCl mediated via a natural kaolinitic clay catalyst; a slightly modified procedure has been describe by Button & Gossage (2003[Button, K. M. & Gossage, R. A. (2003). J. Heterocycl. Chem. 40, 513-517.]) using zinc chloride as a catalyst. Qiao et al. (2011[Qiao, J. X., Wang, T. C., Hu, C., Li, J., Wexler, R. & Lam, P. Y. S. (2011). Org. Lett. 13, 1804-1807.]) described the synthesis of benzoxazole via the reaction of anionically activated tri­fluoro­methyl groups with amino nucleophiles under mild aqueous conditions. Recently, Khalafi-Nezhad & Panahi (2014[Khalafi-Nezhad, A. & Panahi, F. (2014). ACS Catal. 4, 1686-1692.]) reported an efficient approach for the preparation of benzoxazole derivatives, via acceptorless de­hydrogenative coupling of alcohols with 2-amino­phenol using an Ru catalytic system.

In the present work, as part of our ongoing studies of heterocyclic compounds (López-Ruiz et al., 2011[López-Ruiz, H., Briseño-Ortega, H., Rojas-Lima, S., Santillan, R. & Farfán, N. (2011). Tetrahedron Lett. 52, 4308-4312.], 2013[López-Ruiz, H., de la Cerda-Pedro, J. E., Rojas-Lima, S., Pérez-Pérez, I., Rodríguez-Sánchez, B. V., Santillan, R. & Coreño, O. (2013). ARKIVOC, (iii), 139-164; http://www.arkat-usa. org/get-file/47182/.]; de la Cerda-Pedro et al., 2014[Cerda-Pedro, J. E. de la , Amador-Sánchez, Y. A., Cortés-Hernández, M., Pérez-Pérez, J., Rojas-Lima, S. & López-Ruiz, H. (2014). Heterocycles, 89, 27-41.]), we report the synthesis of 2-(2-amino­phen­yl)benzoxazole, we analyse its mol­ecular structure, as well as its weak inter­molecular inter­actions in mol­ecular packing, which could be useful in the understanding of their mode of action in pharmaceutical science, as well as in the design of materials with specific functions. The title compound has been previously reported by Button & Gossage (2003[Button, K. M. & Gossage, R. A. (2003). J. Heterocycl. Chem. 40, 513-517.]) from isatoic anhydride and 2-aminophenol but its crystal structure has not been described.

2. Structural commentary

Compound (I)[link] crystallized in the monoclinic space group P21/c with two independent mol­ecules (A and B) in the asymmetric unit (Fig. 1[link]). The orientation of the amino group can be described using as a basis the carbon atom C9, this orientation is syn to the nitro­gen atom N3 and anti for the oxygen atom O1.

[Figure 1]
Figure 1
The asymmetric unit of (I)[link] with displacement ellipsoids drawn at the 50% probability level (left: mol­ecule A and right: mol­ecule B)

The skeleton of each mol­ecule is practically planar: to analyse the planarity of the mol­ecule we use the torsion angle N3—C2—C8—C9, indicating the rotation of the aromatic ring C8—C13: these angles are −1.2 (2) and 0.9 (2)° for mol­ecules A and B, respectively. The dihedral angles between the benzene ring and the fused ring system are 0.74 (8) and 0.67 (6)° for mol­ecules A and B, respectively. The two independent mol­ecules are very similar, with an r.m.s. overlay fit of 0.019 Å.

3. Supra­molecular features

In the crystal, each NH2 group forms an intra­molecular hydrogen bond of the type N2—H2B⋯N3 (Table 1[link]) with an H⋯N distance of 2.094 (18) Å in mol­ecule A and 2.146 (18) Å in mol­ecule B, and an inter­molecular N2—H2A⋯N2 hydrogen bond with a distance of 2.289 (15) Å for N2—H2A⋯N2′ and 2.522 (16) Å for N2′—H2A′⋯N2, forming zigzag chains propagating in the [100] direction and containing alternating A and B mol­ecules (Fig. 2[link]). Weak aromatic ππ stacking [minimum centroid–centroid separation = 3.6212 (9) Å] links the chains into a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯N2′i 0.92 (2) 2.29 (2) 3.202 (2) 175 (2)
N2—H2B⋯N3 0.92 (1) 2.09 (2) 2.7679 (19) 129 (2)
N2′—H2′A⋯N2ii 0.86 (2) 2.52 (2) 3.359 (2) 164 (2)
N2′—H2′B⋯N3′ 0.89 (1) 2.15 (2) 2.7913 (19) 129 (2)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 2]
Figure 2
Crystal packing for (I)[link], showing the formation of [100] chains. [Symmetry codes: (i) 2 − x, −[{1\over 2}] + y, [{1\over 2}] − z; (ii) 1 − x, −[{1\over 2}] + y, [{1\over 2}] − z; (iii) −x, −[{1\over 2}] + y, [{1\over 2}] − z; (iv) 1 + x, y, z; (v) x, y, z; (vi) 1 − x, 1 − y, 1 − z; (vii) −x, 1 − y, 1 − z; (viii) 1 + x, [{3\over 2}] − y, [{1\over 2}] + z; (ix) x, [{3\over 2}] − y, [{1\over 2}] + z; (x) −1 + x, [{3\over 2}] − y, [{1\over 2}] + z.]

4. Synthesis and crystallization

500 mg (3.00 mmol) of isatoic anhydride were dissolved in 50 mL of m-xylene then 390 mg (3.60 mmol) of o-amino­phenol were added followed by the addition of 0.30 ml (10% mol) of a solution of ZnCl2 (1 M). The mixture was then stirred and heated slowly to reflux temperature during 18 h. The crude reaction product was concentrated on a rotary evaporator with an azeotropic mixture of AcOEt/xylene to obtain a reddish brown solid which was dissolved in EtOAc and washed with 10% aq. NaCl solution. The crude reaction product was purified by column chromatography to give 356 mg (55%) of the amine (I)[link] as a white solid m.p. = 381–382 K (literature value 379–381 K; Button & Gossage, 2003[Button, K. M. & Gossage, R. A. (2003). J. Heterocycl. Chem. 40, 513-517.]); IR (film) γmax cm−1: 3408 NH2, 3051 C—H(arom), 1624 C=N; (literature value IR: 1620 cm−1; Button & Gossage, 2003[Button, K. M. & Gossage, R. A. (2003). J. Heterocycl. Chem. 40, 513-517.]); 1H NMR (CDCl3, 400 MHz): δ = 6.20 (br s, 2H, NH2), 6.79 (m, 2H), 7.29 (m, 1H), 7.33 (m, 2H), 757 (m, 1H), 7.72 (m, 1H), 8.09 (dd, J = 1.6 Hz, J = 8.2 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ = 108.7, 110.4, 116.3, 116.8, 119.4, 124.3, 124.8, 128.8, 132.5, 141.9, 147.9, 149.3, 163.2 [Literature: Button & Gossage (2003[Button, K. M. & Gossage, R. A. (2003). J. Heterocycl. Chem. 40, 513-517.]); 1H NMR δ = 6.15 (br s, 2H, –NH2), 6.74 (m, 2H, ArH), 7.28 (m, 3H, ArH), 7.51 (m, 1H, ArH), 7.67 (m, 1H, ArH), 8.03 (m, 1H, ArH). 13C{1H} NMR δ = 108.7, 110.3, 116.3, 116.8, 119.4, 124.3, 124.7, 128.8, 132.4, 141.9, 147.9, 149.3, 163.2]. Analysis calculated for C13H10N2O: C, 74.27; H, 4.79%; Found: C, 74.43; H, 5.05%.

The single crystal used in the experiment was obtained by the method of liquid–liquid diffusion by slow evaporation. The pure compound was dissolved in the minimum amount of di­chloro­methane to be added by the walls of the tube the same amount of acetone followed by methanol. The tube was sealed to leave the solution in a vibration-free environment at room temperature. After a few days, the solution had evaporated, leaving colourless blocks of the title compound.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. C-bond H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C—H = 0.93 Å (aromatic CH) and with Uiso(H) = 1.2Ueq(C). Hydrogen atoms of the amine group were found in a difference map and refined freely.

Table 2
Experimental details

Crystal data
Chemical formula C13H10N2O
Mr 210.23
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 4.81703 (10), 14.8104 (3), 29.4801 (6)
β (°) 91.3715 (18)
V3) 2102.57 (7)
Z 8
Radiation type Cu Kα
μ (mm−1) 0.69
Crystal size (mm) 0.38 × 0.14 × 0.11
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini
Absorption correction Analytical [CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])]
Tmin, Tmax 0.742, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections 21894, 4278, 3621
Rint 0.032
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.02
No. of reflections 4278
No. of parameters 301
No. of restraints 4
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.14, −0.16
Computer programs: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Chemical context top

Benzimidazole, benzoxazole, and benzo­thia­zole derivatives are key components in many bioactive compounds of both natural and synthetic origin; many are active components of biocides such as bactericides, fungicides, insecticides and anti­carcinogens (Kumar-Samota & Seth, 2010). Benzoxazole derivatives have been used as building blocks for biochemical and pharmaceutical agents, as well as dyes, fluorescent brightening agents, biomarkers and biosensors (Costa et al. 2007 and Tong et al. 2005). In this context, 2-(2-amino­phenyl)­benzoxazole has shown considerable growth inhibition with respect to fungi and gram-positive and gram-negative bacteria (Elnima et al. 1981). For this reason, several methods have been described for the synthesis of these heterocyclic compounds, some of which are summarized in the Scheme, which shows the retrosynthesis for the preparation of the title compound, (I). For example, Gajare et al. (2000) described a procedure for the preparation of 2-(o-amino­phenyl)­oxazolines from isatoic anhydride and 2-o-amino­alcohols at reflux of PhCl mediated via a natural kaolinitic clay catalyst; a slightly modified procedure has been describe by Button & Gossage (2003) using zinc chloride as a catalyst. Qiao et al. (2011) described the synthesis of benzoxazole via the reaction of anionically activated tri­fluoro­methyl groups with amino nucleophiles under mild aqueous conditions. Recently, Khalafi-Nezhad & Panahi (2014) reported an efficient approach for the preparation of benzoxazole derivatives, via acceptorless de­hydrogenative coupling of alcohols with 2-amino­phenol using an Ru catalytic system.

In the present work, as part of our ongoing studies of heterocyclic compounds (López-Ruiz et al., 2011, 2013; de la Cerda-Pedro et al., 2014), we report the synthesis of 2-(2-amino­phenyl)­benzoxazole, we analyse its molecular structure, as well as its weak inter­molecular inter­actions in molecular packing, which could be useful in the understanding of their mode of action in pharmaceutical science, as well as in the design of materials with specific functions. The title compound has been previously reported by Button & Gossage (2003) from isatoic anhydride and 2-amino alcohol but its crystal structure has not been described.

Structural commentary top

Compound (I) crystallized in the monoclinic space group P21/c with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The orientation of the amino group can be described using as a basis the carbon atom C9, this orientation is syn to the nitro­gen atom N3 and anti for the oxygen atom O1.

The skeleton of each molecule is practically planar: to analyse the planarity of the molecule we use the torsion angle N3—C2—C8—C9, indicating the rotation of the aromatic ring C8—C13: these angles are -1.2 (2) and 0.9 (2)° for molecules A and B, respectively. The dihedral angles between the benzene ring and the fused ring system are 0.74 (8) and 0.67 (6)° for molecules A and B, respectively. The two independent molecules are very similar with an r.m.s. overlay fit of 0.019 Å.

Supra­molecular features top

In the crystal, each NH2 group forms an intra­molecular hydrogen bond of the type N2—H2B···N3 (Table 1) with an H···N distance of 2.094 (18) Å in molecule A and 2.146 (18) Å in molecule B, and an inter­molecular N2—H2A···N2 hydrogen bond with a distance of 2.289 (15) Å for N2—H2A···N2' and 2.522 (16) Å for N2'—H2A'···N2, forming zigzag chains propagating in the [100] direction (Fig. 2).

Synthesis and crystallization top

500 mg (3.00 mmol) of isatoic anhydride were dissolved in 50 mL of m-xylene then 390 mg (3.60 mmol) of o-amino­phenol were added followed by the addition of 0.30 ml (10% mol) of a solution of ZnCl2 (1 M). The mixture was then stirred and heated slowly to reflux temperature during 18 h. The crude reaction product was concentrated on a rotary evaporator with an azeotropic mixture of AcOEt/xylene to obtain a reddish brown solid which was dissolved in EtOAc and washed with 10% aq. NaCl solution. The crude reaction product was purified by column chromatography to give 356 mg (55 %) of the amine (I) as a white solid m.p. = 381–382 K (literature value 379–381 K; Button & Gossage, 2003); IR (film) γmax cm-1: 3408 NH2, 3051 C—H(arom), 1624 CN; (literature value IR: 1620 cm-1; Button & Gossage, 2003); 1H NMR (CDCl3, 400 MHz): δ = 6.20 (br s, 2H, NH2), 6.79 (m, 2H), 7.29 (m, 1H), 7.33 (m, 2H), 757 (m, 1H), 7.72 (m, 1H), 8.09 (dd, J = 1.6 Hz, J = 8.2 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ = 108.7, 110.4, 116.3, 116.8, 119.4, 124.3, 124.8, 128.8, 132.5, 141.9, 147.9, 149.3, 163.2 [Literature: Button & Gossage (2003); 1H NMR δ = 6.15 (br s, 2H, -NH2), 6.74 (m, 2H, ArH), 7.28 (m, 3H, ArH), 7.51 (m, 1H, ArH), 7.67 (m, 1H, ArH), 8.03 (m, 1H, ArH). 13C{1H} NMR δ = 108.7, 110.3, 116.3, 116.8, 119.4, 124.3, 124.7, 128.8, 132.4, 141.9, 147.9, 149.3, 163.2]. Analysis calculated for C13H10N2O: C, 74.27; H, 4.79 %; Found: C, 74.43; H, 5.05%.

The single crystal used in the experiment was obtained by the method of liquid–liquid diffusion by slow evaporation. The pure compound was dissolved in the minimum amount of di­chloro­methane to be added by the walls of the tube the same amount of acetone followed by methanol. The tube was sealed to leave the solution in a vibration-free environment at room temperature. After a few days, the solution had evaporated, leaving colourless blocks of the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bond H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C—H = 0.93 Å (aromatic CH) and with Uiso(H) = 1.2Ueq(C). Hydrogen atoms of the amine group were found in a difference map and refined freely.

Related literature top

For related literature, see: Button & Gossage (2003); Costa et al. (2007); Elnima et al. (1981); Gajare et al. (2000); Khalafi-Nezhad & Panahi (2014); Kumar-Samota & Seth (2010); López-Ruiz, Briseño, Ortega, Rojas-Lima, Santillán, Farfán & Tetrahedron Lett (2011); López-Ruiz, de la Cerda-Pedro, Rojas-Lima, Pérez-Pérez, Rodríguez-Sánchez, Santillan & Coreño (2013); Qiao et al. (2011); Tong et al. (2005).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level (left: molecule A and right: molecule B)
[Figure 2] Fig. 2. Crystal packing for (I), showing the formation of [100] chains. [Symmetry codes: (i) 2 - x, -1/2 + y, 1/2 - z; (ii) 1 - x, -1/2 + y, 1/2 - z; (iii) -x, -1/2 + y, 1/2 - z; (iv) 1 + x, y, z; (v) x, y, z; (vi) 1 - x, 1 - y, 1 - z; (vii) -x, 1 - y, 1 - z; (viii) 1 + x, 3/2 - y, 1/2 + z; (ix) x, 3/2 - y, 1/2 + z; (x) -1 + x, 3/2 - y, 1/2 + z.]
2-(2-Aminophenyl)-1,3-benzoxazole top
Crystal data top
C13H10N2ODx = 1.328 Mg m3
Mr = 210.23Melting point: 381 K
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 4.81703 (10) ÅCell parameters from 7503 reflections
b = 14.8104 (3) Åθ = 3.0–74.3°
c = 29.4801 (6) ŵ = 0.69 mm1
β = 91.3715 (18)°T = 293 K
V = 2102.57 (7) Å3Block, colourless
Z = 80.38 × 0.14 × 0.11 mm
F(000) = 880
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer
4278 independent reflections
Radiation source: Enhance (Cu) X-ray Source3621 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 10.3659 pixels mm-1θmax = 74.5°, θmin = 3.0°
ω scansh = 64
Absorption correction: analytical
[CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]
k = 1818
Tmin = 0.742, Tmax = 0.887l = 3636
21894 measured reflections
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.2656P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4278 reflectionsΔρmax = 0.14 e Å3
301 parametersΔρmin = 0.16 e Å3
Crystal data top
C13H10N2OV = 2102.57 (7) Å3
Mr = 210.23Z = 8
Monoclinic, P21/cCu Kα radiation
a = 4.81703 (10) ŵ = 0.69 mm1
b = 14.8104 (3) ÅT = 293 K
c = 29.4801 (6) Å0.38 × 0.14 × 0.11 mm
β = 91.3715 (18)°
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer
4278 independent reflections
Absorption correction: analytical
[CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]
3621 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 0.887Rint = 0.032
21894 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0434 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.14 e Å3
4278 reflectionsΔρmin = 0.16 e Å3
301 parameters
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0170 (2)0.92286 (7)0.34568 (3)0.0625 (3)
O1'0.6575 (2)0.30487 (7)0.46343 (3)0.0605 (3)
N20.4198 (3)0.85716 (10)0.22601 (4)0.0678 (3)
H2A0.559 (4)0.8439 (13)0.2065 (6)0.081*
H2B0.337 (4)0.8108 (11)0.2413 (6)0.081*
N2'0.1130 (3)0.31854 (11)0.34698 (5)0.0703 (4)
H2'A0.034 (4)0.3172 (13)0.3298 (6)0.084*
H2'B0.180 (4)0.2642 (11)0.3545 (7)0.084*
N30.0403 (2)0.81678 (8)0.29206 (4)0.0575 (3)
N3'0.5227 (3)0.23223 (8)0.39963 (4)0.0576 (3)
C20.1126 (3)0.89555 (9)0.30691 (4)0.0532 (3)
C2'0.4906 (3)0.30246 (9)0.42478 (4)0.0533 (3)
C40.3081 (3)0.70682 (12)0.32430 (7)0.0735 (4)
H40.28700.66190.30260.088*
C4'0.8489 (4)0.09914 (11)0.41168 (6)0.0683 (4)
H4'0.79610.06730.38570.082*
C50.4916 (4)0.69714 (13)0.35908 (7)0.0804 (5)
H50.59760.64480.36070.096*
C3A0.1563 (3)0.78613 (10)0.32287 (5)0.0587 (3)
C3A'0.7278 (3)0.18126 (10)0.42227 (5)0.0567 (3)
C5'1.0510 (4)0.06674 (12)0.44134 (6)0.0752 (5)
H5'1.13570.01180.43520.090*
C60.5220 (4)0.76345 (16)0.39167 (7)0.0864 (6)
H60.64700.75430.41480.104*
C6'1.1316 (4)0.11380 (13)0.48016 (6)0.0763 (5)
H6'1.26950.08990.49920.092*
C70.3698 (4)0.84388 (14)0.39075 (6)0.0785 (5)
H70.38870.88900.41240.094*
C7'1.0110 (4)0.19587 (12)0.49121 (5)0.0708 (4)
H7'1.06310.22790.51720.085*
C80.3115 (3)0.95868 (9)0.28832 (4)0.0536 (3)
C7A0.1899 (3)0.85106 (11)0.35532 (5)0.0607 (3)
C7A'0.8096 (3)0.22647 (10)0.46119 (5)0.0574 (3)
C8'0.3042 (3)0.37874 (10)0.41810 (5)0.0564 (3)
C90.4607 (3)0.93665 (10)0.24915 (4)0.0553 (3)
C9'0.1199 (3)0.38352 (11)0.38020 (5)0.0590 (3)
C100.6493 (3)1.00084 (11)0.23331 (5)0.0670 (4)
H100.74790.98830.20730.080*
C10'0.0505 (4)0.46002 (13)0.37630 (6)0.0734 (4)
H10'0.17250.46520.35150.088*
C110.6923 (4)1.08145 (12)0.25509 (6)0.0734 (4)
H110.82031.12230.24390.088*
C11'0.0415 (4)0.52712 (13)0.40806 (7)0.0805 (5)
H11'0.15780.57690.40460.097*
C120.5471 (4)1.10261 (11)0.29352 (6)0.0722 (4)
H120.57651.15750.30820.087*
C12'0.1369 (4)0.52214 (13)0.44503 (7)0.0815 (5)
H12'0.14200.56810.46650.098*
C130.3603 (3)1.04212 (10)0.30963 (5)0.0634 (4)
H130.26241.05650.33550.076*
C13'0.3072 (4)0.44845 (11)0.44974 (6)0.0709 (4)
H13'0.42800.44490.47480.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0665 (6)0.0656 (6)0.0558 (5)0.0094 (5)0.0078 (4)0.0016 (4)
O1'0.0618 (6)0.0648 (6)0.0549 (5)0.0045 (5)0.0013 (4)0.0050 (4)
N20.0683 (8)0.0784 (8)0.0571 (7)0.0071 (7)0.0072 (6)0.0083 (6)
N2'0.0623 (8)0.0896 (9)0.0586 (7)0.0043 (7)0.0046 (6)0.0023 (7)
N30.0519 (7)0.0619 (6)0.0587 (6)0.0081 (5)0.0023 (5)0.0015 (5)
N3'0.0572 (7)0.0621 (6)0.0535 (6)0.0006 (5)0.0038 (5)0.0030 (5)
C20.0505 (7)0.0584 (7)0.0504 (6)0.0132 (6)0.0028 (5)0.0011 (5)
C2'0.0502 (7)0.0615 (7)0.0485 (6)0.0033 (6)0.0054 (5)0.0013 (5)
C40.0572 (9)0.0744 (10)0.0885 (11)0.0002 (7)0.0072 (8)0.0117 (8)
C4'0.0738 (10)0.0631 (8)0.0686 (9)0.0043 (7)0.0107 (8)0.0016 (7)
C50.0558 (9)0.0857 (11)0.0994 (13)0.0001 (8)0.0036 (9)0.0281 (10)
C3A0.0468 (7)0.0663 (8)0.0627 (8)0.0096 (6)0.0060 (6)0.0087 (6)
C3A'0.0555 (8)0.0593 (7)0.0558 (7)0.0024 (6)0.0100 (6)0.0028 (6)
C5'0.0793 (11)0.0663 (9)0.0807 (11)0.0137 (8)0.0157 (9)0.0109 (8)
C60.0597 (10)0.1152 (15)0.0846 (12)0.0099 (10)0.0102 (8)0.0386 (11)
C6'0.0704 (10)0.0836 (11)0.0749 (10)0.0141 (8)0.0036 (8)0.0226 (9)
C70.0724 (11)0.0958 (12)0.0676 (9)0.0158 (9)0.0120 (8)0.0119 (9)
C7'0.0714 (10)0.0821 (10)0.0587 (8)0.0035 (8)0.0009 (7)0.0056 (7)
C80.0497 (7)0.0589 (7)0.0519 (7)0.0097 (6)0.0045 (5)0.0056 (5)
C7A0.0516 (8)0.0693 (8)0.0612 (8)0.0105 (6)0.0002 (6)0.0123 (6)
C7A'0.0553 (8)0.0608 (8)0.0565 (7)0.0016 (6)0.0068 (6)0.0046 (6)
C8'0.0516 (8)0.0620 (7)0.0560 (7)0.0003 (6)0.0084 (6)0.0041 (6)
C90.0508 (8)0.0651 (7)0.0498 (6)0.0117 (6)0.0053 (5)0.0033 (6)
C9'0.0491 (8)0.0746 (9)0.0538 (7)0.0041 (6)0.0107 (6)0.0103 (6)
C100.0612 (9)0.0797 (10)0.0603 (8)0.0094 (8)0.0057 (7)0.0103 (7)
C10'0.0582 (9)0.0937 (12)0.0684 (9)0.0094 (8)0.0059 (7)0.0210 (8)
C110.0681 (10)0.0721 (9)0.0799 (10)0.0009 (8)0.0014 (8)0.0171 (8)
C11'0.0741 (11)0.0815 (11)0.0865 (12)0.0231 (9)0.0164 (9)0.0173 (9)
C120.0804 (11)0.0594 (8)0.0765 (10)0.0002 (8)0.0034 (8)0.0037 (7)
C12'0.0881 (13)0.0732 (10)0.0835 (11)0.0182 (9)0.0080 (9)0.0049 (9)
C130.0676 (9)0.0636 (8)0.0592 (8)0.0094 (7)0.0039 (7)0.0005 (6)
C13'0.0731 (11)0.0717 (9)0.0677 (9)0.0098 (8)0.0004 (8)0.0062 (7)
Geometric parameters (Å, º) top
O1—C21.3763 (16)C6—H60.9300
O1—C7A1.3842 (19)C6—C71.399 (3)
O1'—C2'1.3791 (16)C6'—H6'0.9300
O1'—C7A'1.3756 (17)C6'—C7'1.389 (2)
N2—H2A0.916 (15)C7—H70.9300
N2—H2B0.919 (14)C7—C7A1.377 (2)
N2—C91.372 (2)C7'—H7'0.9300
N2'—H2'A0.861 (15)C7'—C7A'1.374 (2)
N2'—H2'B0.894 (14)C8—C91.4129 (19)
N2'—C9'1.373 (2)C8—C131.404 (2)
N3—C21.2910 (18)C8'—C9'1.412 (2)
N3—C3A1.4033 (19)C8'—C13'1.391 (2)
N3'—C2'1.2889 (18)C9—C101.403 (2)
N3'—C3A'1.4001 (19)C9'—C10'1.402 (2)
C2—C81.455 (2)C10—H100.9300
C2'—C8'1.454 (2)C10—C111.369 (3)
C4—H40.9300C10'—H10'0.9300
C4—C51.377 (3)C10'—C11'1.365 (3)
C4—C3A1.385 (2)C11—H110.9300
C4'—H4'0.9300C11—C121.382 (3)
C4'—C3A'1.388 (2)C11'—H11'0.9300
C4'—C5'1.379 (2)C11'—C12'1.374 (3)
C5—H50.9300C12—H120.9300
C5—C61.384 (3)C12—C131.363 (2)
C3A—C7A1.369 (2)C12'—H12'0.9300
C3A'—C7A'1.378 (2)C12'—C13'1.370 (2)
C5'—H5'0.9300C13—H130.9300
C5'—C6'1.387 (3)C13'—H13'0.9300
C2—O1—C7A103.41 (11)C7A'—C7'—C6'115.48 (16)
C7A'—O1'—C2'103.83 (11)C7A'—C7'—H7'122.3
H2A—N2—H2B118.9 (17)C9—C8—C2120.78 (13)
C9—N2—H2A113.5 (12)C13—C8—C2120.11 (13)
C9—N2—H2B117.1 (12)C13—C8—C9119.10 (14)
H2'A—N2'—H2'B114.5 (19)C3A—C7A—O1108.32 (13)
C9'—N2'—H2'A116.2 (14)C3A—C7A—C7124.26 (17)
C9'—N2'—H2'B116.8 (13)C7—C7A—O1127.41 (16)
C2—N3—C3A104.68 (12)O1'—C7A'—C3A'107.95 (13)
C2'—N3'—C3A'104.70 (12)C7'—C7A'—O1'128.04 (14)
O1—C2—C8116.10 (12)C7'—C7A'—C3A'124.01 (15)
N3—C2—O1115.04 (13)C9'—C8'—C2'121.39 (13)
N3—C2—C8128.86 (13)C13'—C8'—C2'119.30 (14)
O1'—C2'—C8'115.96 (12)C13'—C8'—C9'119.31 (14)
N3'—C2'—O1'114.88 (12)N2—C9—C8122.32 (14)
N3'—C2'—C8'129.16 (13)N2—C9—C10120.15 (14)
C5—C4—H4121.3C10—C9—C8117.49 (14)
C5—C4—C3A117.38 (18)N2'—C9'—C8'122.22 (14)
C3A—C4—H4121.3N2'—C9'—C10'120.26 (15)
C3A'—C4'—H4'121.4C10'—C9'—C8'117.45 (15)
C5'—C4'—H4'121.4C9—C10—H10119.1
C5'—C4'—C3A'117.16 (16)C11—C10—C9121.80 (15)
C4—C5—H5119.2C11—C10—H10119.1
C4—C5—C6121.56 (18)C9'—C10'—H10'119.2
C6—C5—H5119.2C11'—C10'—C9'121.53 (16)
C4—C3A—N3131.24 (15)C11'—C10'—H10'119.2
C7A—C3A—N3108.55 (13)C10—C11—H11119.7
C7A—C3A—C4120.21 (15)C10—C11—C12120.57 (16)
C4'—C3A'—N3'131.37 (14)C12—C11—H11119.7
C7A'—C3A'—N3'108.64 (13)C10'—C11'—H11'119.5
C7A'—C3A'—C4'120.00 (15)C10'—C11'—C12'120.94 (17)
C4'—C5'—H5'119.1C12'—C11'—H11'119.5
C4'—C5'—C6'121.84 (16)C11—C12—H12120.4
C6'—C5'—H5'119.1C13—C12—C11119.20 (16)
C5—C6—H6119.1C13—C12—H12120.4
C5—C6—C7121.76 (17)C11'—C12'—H12'120.5
C7—C6—H6119.1C13'—C12'—C11'118.99 (18)
C5'—C6'—H6'119.2C13'—C12'—H12'120.5
C5'—C6'—C7'121.52 (16)C8—C13—H13119.1
C7'—C6'—H6'119.2C12—C13—C8121.83 (15)
C6—C7—H7122.6C12—C13—H13119.1
C7A—C7—C6114.83 (18)C8'—C13'—H13'119.1
C7A—C7—H7122.6C12'—C13'—C8'121.77 (17)
C6'—C7'—H7'122.3C12'—C13'—H13'119.1
O1—C2—C8—C9178.67 (11)C5—C4—C3A—N3178.83 (15)
O1—C2—C8—C130.43 (18)C5—C4—C3A—C7A0.4 (2)
O1'—C2'—C8'—C9'179.01 (12)C5—C6—C7—C7A0.2 (3)
O1'—C2'—C8'—C13'0.9 (2)C3A—N3—C2—O10.01 (15)
N2—C9—C10—C11178.96 (15)C3A—N3—C2—C8179.91 (13)
N2'—C9'—C10'—C11'177.83 (16)C3A—C4—C5—C60.6 (3)
N3—C2—C8—C91.2 (2)C3A'—N3'—C2'—O1'0.00 (16)
N3—C2—C8—C13179.67 (14)C3A'—N3'—C2'—C8'179.94 (13)
N3—C3A—C7A—O10.04 (15)C3A'—C4'—C5'—C6'0.1 (3)
N3—C3A—C7A—C7179.31 (14)C5'—C4'—C3A'—N3'179.39 (15)
N3'—C2'—C8'—C9'0.9 (2)C5'—C4'—C3A'—C7A'0.4 (2)
N3'—C2'—C8'—C13'179.17 (15)C5'—C6'—C7'—C7A'0.1 (3)
N3'—C3A'—C7A'—O1'0.35 (16)C6—C7—C7A—O1179.19 (14)
N3'—C3A'—C7A'—C7'179.14 (14)C6—C7—C7A—C3A0.0 (2)
C2—O1—C7A—C3A0.05 (14)C6'—C7'—C7A'—O1'179.79 (15)
C2—O1—C7A—C7179.29 (15)C6'—C7'—C7A'—C3A'0.4 (2)
C2—N3—C3A—C4179.31 (15)C8—C9—C10—C111.0 (2)
C2—N3—C3A—C7A0.02 (15)C7A—O1—C2—N30.03 (15)
C2—C8—C9—N22.2 (2)C7A—O1—C2—C8179.95 (11)
C2—C8—C9—C10179.83 (12)C7A'—O1'—C2'—N3'0.21 (15)
C2—C8—C13—C12179.28 (14)C7A'—O1'—C2'—C8'179.85 (12)
C2'—O1'—C7A'—C3A'0.33 (14)C8'—C9'—C10'—C11'0.6 (2)
C2'—O1'—C7A'—C7'179.14 (15)C9—C8—C13—C120.2 (2)
C2'—N3'—C3A'—C4'179.99 (15)C9—C10—C11—C120.7 (3)
C2'—N3'—C3A'—C7A'0.21 (16)C9'—C8'—C13'—C12'0.4 (3)
C2'—C8'—C9'—N2'2.3 (2)C9'—C10'—C11'—C12'0.3 (3)
C2'—C8'—C9'—C10'179.43 (13)C10—C11—C12—C130.1 (3)
C2'—C8'—C13'—C12'179.70 (16)C10'—C11'—C12'—C13'0.0 (3)
C4—C5—C6—C70.5 (3)C11—C12—C13—C80.2 (3)
C4—C3A—C7A—O1179.43 (13)C11'—C12'—C13'—C8'0.1 (3)
C4—C3A—C7A—C70.1 (2)C13—C8—C9—N2178.64 (13)
C4'—C3A'—C7A'—O1'179.83 (13)C13—C8—C9—C100.72 (19)
C4'—C3A'—C7A'—C7'0.7 (2)C13'—C8'—C9'—N2'177.80 (15)
C4'—C5'—C6'—C7'0.4 (3)C13'—C8'—C9'—C10'0.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N2i0.92 (2)2.29 (2)3.202 (2)175 (2)
N2—H2B···N30.92 (1)2.09 (2)2.7679 (19)129 (2)
N2—H2A···N2ii0.86 (2)2.52 (2)3.359 (2)164 (2)
N2—H2B···N30.89 (1)2.15 (2)2.7913 (19)129 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N2'i0.916 (15)2.289 (15)3.202 (2)175.0 (17)
N2—H2B···N30.919 (14)2.094 (18)2.7679 (19)129.2 (16)
N2'—H2'A···N2ii0.861 (15)2.522 (16)3.359 (2)164.0 (18)
N2'—H2'B···N3'0.894 (14)2.146 (18)2.7913 (19)128.5 (17)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H10N2O
Mr210.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)4.81703 (10), 14.8104 (3), 29.4801 (6)
β (°) 91.3715 (18)
V3)2102.57 (7)
Z8
Radiation typeCu Kα
µ (mm1)0.69
Crystal size (mm)0.38 × 0.14 × 0.11
Data collection
DiffractometerAgilent Xcalibur Atlas Gemini
diffractometer
Absorption correctionAnalytical
[CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.742, 0.887
No. of measured, independent and
observed [I > 2σ(I)] reflections
21894, 4278, 3621
Rint0.032
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.02
No. of reflections4278
No. of parameters301
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.16

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

We gratefully acknowledge financial support from CONACyT (CB-2012–01-182415, CB-2009–135172). IPP is also grateful to CONACyT for a scholarship (grant 206301) to support her studies.

References

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Volume 71| Part 2| February 2015| Pages 188-191
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