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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 133-135
doi:10.1107/S2056989016000128

Crystal structure of 1-benzyl-4-formyl-1H-pyrrole-3-carb­oxamide

CROSSMARK_Color_square_no_text.svg
Qi-Di Zhong,a Sheng-Quan Hua and Hong Yana*

aCollege of Life Science and Bio-Engineering, Beijing University of Technology, 100124 Chaoyang District, Beijing, People's Republic of China
*Correspondence e-mail: hongyan@bjut.edu.cn

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 23 December 2015; accepted 4 January 2016; online 9 January 2016)

In the title compound, C13H12N2O2 (I), the mean planes of the pyrrole and benzyl rings are approximately perpendicular, forming a dihedral angle of 87.07 (4) °. There is an intra­molecular N—H⋯O hydrogen bond forming an S(7) ring motif. In the crystal, mol­ecules are linked via a pair of N—H⋯O hydrogen bonds forming inversion dimers. C—H⋯O hydrogen bonds link the dimers into chains along direction [10-1]. The chains are further linked by weak C—H⋯π inter­actions forming layers parallel to the ac plane.

CCDC reference: 1445256

1. Chemical context

Pyrrole and its derivatives are classes of heterocyclic compounds and that have attracted much attention because of their potential pharmacological and biological properties (Davis et al., 2008[Davis, F. A., Bowen, K., Xu, H. & Velvadapu, V. (2008). Tetrahedron, 64, 4174-4182.]; Meshram et al., 2010[Meshram, H. M., Prasad, B. R. V. & Kumar, D. A. (2010). Tetrahedron Lett. 51, 3477-3480.]; Moriguchi et al., 2015[Moriguchi, T., Jalli, V., Krishnamurthy, S., Tsuge, A. & Yoza, K. (2015). Acta Cryst. E71, o1049-o1050.]). As a part of our work on the synthesis of new pyrrole derivatives with good biological activities, the title compound, (I)[link], was synthesized and its crystal structure is reported on herein.

[Scheme 1]

2. Structural commentary

The mol­ecular structure of the title compound (I)[link], is shown in Fig. 1[link]. In the amide group, the C—N bond is relatively short [C12—N2 = 1.3374 (16) Å], suggesting some degree of electronic delocalization in the mol­ecule. The dihedral angle between the pyrrole and phenyl rings is 87.07 (4)°, indicating that they are nearly perpendicular to each other. An intra­molecular hydrogen bond, N2—H2B⋯O2 (Table 1[link]), encloses an S(7) ring motif.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzyl ring C1–C6.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2B⋯O2 0.86 1.99 2.8184 (14) 160
N2—H2A⋯O1i 0.86 2.22 3.0063 (14) 151
C8—H8⋯O1ii 0.93 2.69 3.4252 (15) 136
C7—H7B⋯O1ii 0.97 2.48 3.3123 (15) 144
C7—H7A⋯O2iii 0.97 2.66 3.3268 (15) 126
C11—H11⋯Cg1iv 0.93 2.58 3.4962 (14) 167
Symmetry codes: (i) -x+1, -y+2, -z-1; (ii) -x+2, -y+2, -z; (iii) x+1, y, z+1; (iv) x-1, y, z.
[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound (I)[link], with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

3. Supra­molecular features

In the crystal of (I)[link], N2—H2A⋯O1i hydrogen bonds [symmetry code: (i) −x + 1, −y + 2, −z − 1], link pairs of mol­ecules, forming inversion dimers with an R22(8) ring motif (Table 1[link] and Fig. 2[link]). The dimers are further linked by C7—H7B⋯O1ii, C8—H8⋯O1ii and C7—H7A⋯O2iii hydrogen bonds [symmetry codes: (ii) −x + 2, −y + 2, −z; (iii) x + 1, y, z + 1] into supra­molecular chains propagating along [10[\overline{1}]]; see Table 1[link] and Fig. 3[link]). Adjacent chains are linked by weak C11—H11⋯Cg1iv contacts [Cg1 is the centroid of the C1—C6 benzyl ring; symmetry code: (iv) − 1 + x, y, z], forming layers parallel to the ac plane (Table 1[link] and Fig. 4[link]).

[Figure 2]
Figure 2
A view of the inversion dimer formed by pairs of N—H⋯O hydrogen bonds. Both the intra­molecular and inter­molecular hydrogen bonds are shown as dashed lines (see Table 1[link]).
[Figure 3]
Figure 3
A view of the one-dimensional chain structure. The dashed lines indicate the N—H⋯O and C—H⋯O hydrogen bonds (see Table 1[link]).
[Figure 4]
Figure 4
The view of the two-dimensional network structure. The C—H⋯π inter­actions and the hydrogen bonds are shown with green and purple dashed lines, respectively (see Table 1[link]).

4. Database survey

A search of the Cambridge Structural Database (Version 5.36 with three updates; Groom & Allen, 2014) for 1-benzyl-4-formyl-1H-pyrrole-3-carb­oxamide gave no hits. However, structures of substituted derivatives of 1-benzyl-1H-pyrrole were found, see for example Bonnett et al. (1985[Bonnett, R., Hursthouse, M. B., North, S. A. & Trotter, J. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 293-296.]); Choi et al. (1998[Choi, D. S., Huang, S., Huang, M., Barnard, T. S., Adams, R. D., Seminario, J. M. & Tour, J. M. (1998). J. Org. Chem. 63, 2646-2655.]); Sha et al. (1990[Sha, C. K., Liu, J. M., Chiang, R. K. & Wang, S. L. (1990). Heterocycles, 31, 603-609.]); Wang et al. (2011[Wang, Z., Li, K., Zhao, D., Lan, J. & You, J. (2011). Angew. Chem. Int. Ed. 50, 5365-5369.]). In these structures, the pyrrole and benzyl rings are also nearly perpendicular to one another.

5. Synthesis and crystallization

1-Benzyl-1H-pyrrole-3-carb­oxamide (1 mmol, 214.3 mg) was dissolved in methanol (20 ml) and irradiated with UV light at room temperature under oxygen (see Scheme). The reaction progress was monitored by thin layer chromatography (TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel, using a mixed solvent of petroleum ether and ethyl acetate (10:1 ratio, v/v), to give the pure product. Colourless single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a methanol solution of the title compound at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(N,C).

Table 2
Experimental details

Crystal data
Chemical formula C13H12N2O2
Mr 228.25
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 5.5296 (6), 23.083 (3), 9.3088 (9)
β (°) 112.940 (5)
V (Å3) 1094.2 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.25 × 0.20 × 0.18
 
Data collection
Diffractometer Bruker SMART CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections 9372, 1938, 1823
Rint 0.021
(sin θ/λ)max (Å−1) 0.596
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.123, 1.00
No. of reflections 1938
No. of parameters 154
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.26
Computer programs: APEX2 and SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1445256

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989016000128/su5268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016000128/su5268Isup2.hkl

checkCIF report


Chemical context top

Pyrrole and its derivatives are classes of heterocyclic compounds and that have attracted much attention because of their potential pharmacological and biological properties (Davis et al., 2008; Meshram et al., 2010; Moriguchi et al., 2015). As a part of our work on the synthesis of new pyrrole derivatives with good biological activities, the title compound, (I), was synthesized and its crystal structure is reported on herein.

Structural commentary top

The molecular structure of the title compound (I), is shown in Fig. 1. In the amide group, the C—N bond is relatively short, suggesting some degree of electronic delocalization in the molecule. The dihedral angle between the pyrrole and phenyl rings is 87.07 (4)°, indicating that they are nearly perpendicular to each other. An intra­molecular hydrogen bond, N2—H2B···O2 (Table 1), encloses an S(7) ring motif.

Supra­molecular features top

In the crystal of (I), N2—H2A···O1i hydrogen bonds [symmetry code: (i) −x + 1, −y + 2, −z − 1], link pairs of molecules, forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2). The dimers are further linked by C7—H7B···O1ii, C8—H8···O1ii and C7—H7A···O2iii hydrogen bonds [symmetry codes: (ii) −x + 2, −y + 2, −z; (iii) x + 1, y, z + 1] into supra­molecular chains propagating along [101]; see Table 1 and Fig. 3). Adjacent chains are linked by weak C11—H11···Cg1iv contacts [Cg1 is the centroid of the C1—C6 benzyl ring; symmetry code: (iv) − 1 + x, y, z], forming layers parallel to the ac plane (Table 1 and Fig. 4).

Database survey top

A search of the Cambridge Structural Database (Version 5.36 with three updates; Groom & Allen, 2014) for 1-benzyl-4-formyl-1H-pyrrole-3-carboxamide gave no hits. However, structures of substituted derivatives of 1-benzyl-1H-pyrrole were found, see for example Bonnett et al. (1985); Choi et al. (1998); Sha et al. (1990); Wang et al. (2011). In these structures, the pyrrole and benzyl rings are also nearly perpendicular to one another.

Synthesis and crystallization top

1-Benzyl-1H-pyrrole-3-carboxamide (1 mmol, 199.0 mg) was dissolved in methanol (20 ml) and irradiated with UV light at room temperature under oxygen (see Scheme). The reaction progress was monitored by thin layer chromatography (TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel, using a mixed solvent of petroleum ether and ethyl acetate (10:1 ratio, v/v), to give the pure product. Colourless single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a methanol solution of the title compound at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(N,C).

Structure description top

Pyrrole and its derivatives are classes of heterocyclic compounds and that have attracted much attention because of their potential pharmacological and biological properties (Davis et al., 2008; Meshram et al., 2010; Moriguchi et al., 2015). As a part of our work on the synthesis of new pyrrole derivatives with good biological activities, the title compound, (I), was synthesized and its crystal structure is reported on herein.

The molecular structure of the title compound (I), is shown in Fig. 1. In the amide group, the C—N bond is relatively short, suggesting some degree of electronic delocalization in the molecule. The dihedral angle between the pyrrole and phenyl rings is 87.07 (4)°, indicating that they are nearly perpendicular to each other. An intra­molecular hydrogen bond, N2—H2B···O2 (Table 1), encloses an S(7) ring motif.

In the crystal of (I), N2—H2A···O1i hydrogen bonds [symmetry code: (i) −x + 1, −y + 2, −z − 1], link pairs of molecules, forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2). The dimers are further linked by C7—H7B···O1ii, C8—H8···O1ii and C7—H7A···O2iii hydrogen bonds [symmetry codes: (ii) −x + 2, −y + 2, −z; (iii) x + 1, y, z + 1] into supra­molecular chains propagating along [101]; see Table 1 and Fig. 3). Adjacent chains are linked by weak C11—H11···Cg1iv contacts [Cg1 is the centroid of the C1—C6 benzyl ring; symmetry code: (iv) − 1 + x, y, z], forming layers parallel to the ac plane (Table 1 and Fig. 4).

A search of the Cambridge Structural Database (Version 5.36 with three updates; Groom & Allen, 2014) for 1-benzyl-4-formyl-1H-pyrrole-3-carboxamide gave no hits. However, structures of substituted derivatives of 1-benzyl-1H-pyrrole were found, see for example Bonnett et al. (1985); Choi et al. (1998); Sha et al. (1990); Wang et al. (2011). In these structures, the pyrrole and benzyl rings are also nearly perpendicular to one another.

Synthesis and crystallization top

1-Benzyl-1H-pyrrole-3-carboxamide (1 mmol, 199.0 mg) was dissolved in methanol (20 ml) and irradiated with UV light at room temperature under oxygen (see Scheme). The reaction progress was monitored by thin layer chromatography (TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by chromatography on silica gel, using a mixed solvent of petroleum ether and ethyl acetate (10:1 ratio, v/v), to give the pure product. Colourless single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a methanol solution of the title compound at room temperature.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(N,C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound (I), with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the inversion dimer formed by pairs of N—H···O hydrogen bonds. Both the intramolecular and intermolecular hydrogen bonds are shown as dashed lines (see Table 1).
[Figure 3] Fig. 3. A view of the one-dimensional chain structure. The dashed lines indicate the N—H···O and C—H···O hydrogen bonds (see Table 1).
[Figure 4] Fig. 4. The view of the two-dimensional network structure. The C—H···π interactions and the hydrogen bonds are shown with green and purple dashed lines, respectively (see Table 1).
1-Benzyl-4-formyl-1H-pyrrole-3-carboxamide top
Crystal data top
C13H12N2O2F(000) = 480
Mr = 228.25Dx = 1.386 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3196 reflections
a = 5.5296 (6) Åθ = 3.5–27.5°
b = 23.083 (3) ŵ = 0.10 mm−1
c = 9.3088 (9) ÅT = 293 K
β = 112.940 (5)°Block, colorless
V = 1094.2 (2) Å30.25 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		1938 independent reflections
Radiation source: fine-focus sealed tube1823 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
phi and ω scansθmax = 25.1°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −6→6
Tmin = 0.977, Tmax = 0.983k = −27→27
9372 measured reflectionsl = −11→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.2118P]
where P = (Fo2 + 2Fc2)/3
1938 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C13H12N2O2V = 1094.2 (2) Å3
Mr = 228.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.5296 (6) ŵ = 0.10 mm−1
b = 23.083 (3) ÅT = 293 K
c = 9.3088 (9) Å0.25 × 0.20 × 0.18 mm
β = 112.940 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1938 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1823 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.983Rint = 0.021
9372 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.00Δρmax = 0.19 e Å−3
1938 reflectionsΔρmin = −0.26 e Å−3
154 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0335 (2)0.84645 (5)0.26085 (13)0.0165 (3)
C20.9577 (2)0.80281 (5)0.14829 (15)0.0217 (3)
H20.79040.80350.06960.026*
C31.1293 (3)0.75831 (6)0.15255 (17)0.0267 (3)
H31.07740.72980.07600.032*
C41.3792 (3)0.75629 (6)0.27120 (17)0.0271 (3)
H41.49420.72640.27460.033*
C51.4545 (2)0.79918 (6)0.38396 (15)0.0252 (3)
H51.62040.79790.46400.030*
C61.2845 (2)0.84412 (5)0.37859 (14)0.0206 (3)
H61.33850.87300.45430.025*
C70.8542 (2)0.89645 (5)0.25832 (13)0.0167 (3)
H7A0.75950.88690.32360.020*
H7B0.96010.93050.30220.020*
C80.7226 (2)0.94298 (5)−0.00412 (13)0.0158 (3)
H80.87920.96270.01640.019*
C90.5118 (2)0.94220 (5)−0.14451 (13)0.0152 (3)
C100.3150 (2)0.90594 (5)−0.12295 (13)0.0162 (3)
C110.4214 (2)0.88767 (5)0.03064 (13)0.0171 (3)
H110.33830.86380.07790.021*
C120.5128 (2)0.97561 (5)−0.28041 (13)0.0171 (3)
C130.0602 (2)0.88460 (5)−0.22590 (14)0.0199 (3)
H13−0.02880.8620−0.17970.024*
N10.66548 (19)0.90998 (4)0.10118 (11)0.0152 (3)
N20.2915 (2)0.97471 (5)−0.40897 (12)0.0214 (3)
H2A0.28250.9936−0.49060.026*
H2B0.15810.9553−0.41000.026*
O10.71039 (17)1.00283 (4)−0.27249 (10)0.0237 (3)
O2−0.05271 (17)0.89275 (4)−0.36651 (10)0.0255 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0178 (6)0.0173 (6)0.0150 (6)−0.0021 (5)0.0072 (5)0.0043 (4)
C20.0162 (6)0.0221 (7)0.0233 (7)−0.0031 (5)0.0041 (5)−0.0016 (5)
C30.0249 (7)0.0193 (7)0.0347 (8)−0.0027 (5)0.0103 (6)−0.0052 (5)
C40.0234 (7)0.0199 (7)0.0380 (8)0.0052 (5)0.0120 (6)0.0061 (5)
C50.0181 (6)0.0284 (7)0.0244 (7)0.0026 (5)0.0033 (5)0.0086 (5)
C60.0209 (6)0.0228 (7)0.0159 (6)−0.0023 (5)0.0046 (5)0.0020 (5)
C70.0167 (6)0.0198 (6)0.0113 (6)−0.0003 (5)0.0029 (5)0.0011 (4)
C80.0156 (6)0.0153 (6)0.0163 (6)−0.0010 (4)0.0062 (5)0.0001 (4)
C90.0160 (6)0.0142 (6)0.0147 (6)0.0013 (4)0.0051 (5)−0.0014 (4)
C100.0153 (6)0.0175 (6)0.0154 (6)0.0012 (5)0.0057 (5)−0.0008 (4)
C110.0155 (6)0.0183 (6)0.0185 (6)−0.0017 (5)0.0076 (5)0.0004 (5)
C120.0200 (6)0.0144 (6)0.0162 (6)0.0009 (5)0.0064 (5)−0.0008 (4)
C130.0171 (6)0.0221 (6)0.0194 (7)−0.0005 (5)0.0059 (5)−0.0007 (5)
N10.0155 (5)0.0164 (5)0.0120 (5)0.0006 (4)0.0037 (4)0.0007 (4)
N20.0198 (6)0.0265 (6)0.0149 (5)−0.0022 (4)0.0034 (4)0.0055 (4)
O10.0233 (5)0.0275 (5)0.0177 (5)−0.0062 (4)0.0052 (4)0.0042 (3)
O20.0213 (5)0.0314 (6)0.0178 (5)−0.0034 (4)0.0009 (4)−0.0008 (4)
Geometric parameters (Å, º) top
C1—C61.3942 (17)C8—C91.3709 (16)
C1—C21.3949 (18)C8—N11.3719 (15)
C1—C71.5159 (16)C8—H80.9300
C2—C31.3886 (18)C9—C101.4476 (16)
C2—H20.9300C9—C121.4834 (16)
C3—C41.3933 (19)C10—C111.3829 (16)
C3—H30.9300C10—C131.4471 (17)
C4—C51.384 (2)C11—N11.3516 (15)
C4—H40.9300C11—H110.9300
C5—C61.3877 (18)C12—O11.2375 (15)
C5—H50.9300C12—N21.3374 (16)
C6—H60.9300C13—O21.2253 (15)
C7—N11.4616 (14)C13—H130.9300
C7—H7A0.9700N2—H2A0.8600
C7—H7B0.9700N2—H2B0.8600
C6—C1—C2118.58 (11)C9—C8—N1109.08 (10)
C6—C1—C7119.09 (11)C9—C8—H8125.5
C2—C1—C7122.33 (11)N1—C8—H8125.5
C3—C2—C1120.71 (12)C8—C9—C10106.34 (10)
C3—C2—H2119.6C8—C9—C12121.46 (11)
C1—C2—H2119.6C10—C9—C12132.19 (11)
C2—C3—C4120.19 (12)C11—C10—C13119.54 (11)
C2—C3—H3119.9C11—C10—C9106.24 (10)
C4—C3—H3119.9C13—C10—C9134.08 (11)
C5—C4—C3119.32 (12)N1—C11—C10109.15 (10)
C5—C4—H4120.3N1—C11—H11125.4
C3—C4—H4120.3C10—C11—H11125.4
C4—C5—C6120.55 (12)O1—C12—N2122.68 (11)
C4—C5—H5119.7O1—C12—C9120.65 (10)
C6—C5—H5119.7N2—C12—C9116.67 (10)
C5—C6—C1120.65 (12)O2—C13—C10127.90 (12)
C5—C6—H6119.7O2—C13—H13116.0
C1—C6—H6119.7C10—C13—H13116.0
N1—C7—C1112.69 (9)C11—N1—C8109.20 (10)
N1—C7—H7A109.1C11—N1—C7126.38 (10)
C1—C7—H7A109.1C8—N1—C7124.07 (10)
N1—C7—H7B109.1C12—N2—H2A120.0
C1—C7—H7B109.1C12—N2—H2B120.0
H7A—C7—H7B107.8H2A—N2—H2B120.0
C6—C1—C2—C3−0.61 (18)C12—C9—C10—C136.5 (2)
C7—C1—C2—C3178.65 (11)C13—C10—C11—N1176.01 (10)
C1—C2—C3—C40.9 (2)C9—C10—C11—N1−0.30 (13)
C2—C3—C4—C5−0.3 (2)C8—C9—C12—O13.69 (18)
C3—C4—C5—C6−0.6 (2)C10—C9—C12—O1−178.07 (11)
C4—C5—C6—C10.92 (19)C8—C9—C12—N2−176.06 (10)
C2—C1—C6—C5−0.30 (18)C10—C9—C12—N22.19 (19)
C7—C1—C6—C5−179.59 (11)C11—C10—C13—O2−173.94 (12)
C6—C1—C7—N1151.87 (11)C9—C10—C13—O21.1 (2)
C2—C1—C7—N1−27.39 (15)C10—C11—N1—C80.01 (13)
N1—C8—C9—C10−0.47 (13)C10—C11—N1—C7−173.30 (10)
N1—C8—C9—C12178.17 (10)C9—C8—N1—C110.30 (13)
C8—C9—C10—C110.47 (13)C9—C8—N1—C7173.80 (10)
C12—C9—C10—C11−177.97 (12)C1—C7—N1—C1190.92 (13)
C8—C9—C10—C13−175.05 (13)C1—C7—N1—C8−81.44 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the benzyl ring C1–C6.
D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.861.992.8184 (14)160
N2—H2A···O1i0.862.223.0063 (14)151
C8—H8···O1ii0.932.693.4252 (15)136
C7—H7B···O1ii0.972.483.3123 (15)144
C7—H7A···O2iii0.972.663.3268 (15)126
C11—H11···Cg1iv0.932.583.4962 (14)167
Symmetry codes: (i) −x+1, −y+2, −z−1; (ii) −x+2, −y+2, −z; (iii) x+1, y, z+1; (iv) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the benzyl ring C1–C6.
D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.861.992.8184 (14)160
N2—H2A···O1i0.862.223.0063 (14)151
C8—H8···O1ii0.932.693.4252 (15)136
C7—H7B···O1ii0.972.483.3123 (15)144
C7—H7A···O2iii0.972.663.3268 (15)126
C11—H11···Cg1iv0.932.583.4962 (14)167
Symmetry codes: (i) −x+1, −y+2, −z−1; (ii) −x+2, −y+2, −z; (iii) x+1, y, z+1; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC13H12N2O2
Mr228.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)5.5296 (6), 23.083 (3), 9.3088 (9)
β (°) 112.940 (5)
V (Å3)1094.2 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.977, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections		9372, 1938, 1823
Rint0.021
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.123, 1.00
No. of reflections1938
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) (Sheldrick, 2008), SHELXTL.

 

Acknowledgements

This work was supported financially by the Key Projects in the Beijing Municipal Natural Science Foundation (No. KZ201510005007).

References

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ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 133-135
doi:10.1107/S2056989016000128
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