research communications
H-pyrrole-3-carboxamide
of 1-benzyl-4-formyl-1aCollege 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
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 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 is reported on herein.
and that have attracted much attention because of their potential pharmacological and biological properties (Davis2. Structural commentary
The molecular structure of the title compound (I), is shown in Fig. 1. 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), encloses an S(7) ring motif.
3. Supramolecular features
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 [10]; 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).
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); 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.
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 (TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by 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 were obtained by slow evaporation of a methanol solution of the title compound at room temperature.
6. Refinement
Crystal data, data collection and structure . 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).
details are summarized in Table 2
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Supporting information
CCDC reference: 1445256
10.1107/S2056989016000128/su5268sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016000128/su5268Isup2.hkl
Pyrrole and its derivatives are classes of
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 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.
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
(TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by 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 were obtained by slow evaporation of a methanol solution of the title compound at room temperature.Pyrrole and its derivatives are classes of
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 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.
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
(TLC). After completion, the solvent was removed under reduced pressure, and the residue was purified by 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 were obtained by slow evaporation of a methanol solution of the title compound at room temperature. detailsCrystal data, data collection and structure
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).Data collection: APEX2 (Bruker, 2005); cell
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.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. | |
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). | |
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). | |
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). |
C13H12N2O2 | F(000) = 480 |
Mr = 228.25 | Dx = 1.386 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3196 reflections |
a = 5.5296 (6) Å | θ = 3.5–27.5° |
b = 23.083 (3) Å | µ = 0.10 mm−1 |
c = 9.3088 (9) Å | T = 293 K |
β = 112.940 (5)° | Block, colorless |
V = 1094.2 (2) Å3 | 0.25 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1938 independent reflections |
Radiation source: fine-focus sealed tube | 1823 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
phi and ω scans | θmax = 25.1°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −6→6 |
Tmin = 0.977, Tmax = 0.983 | k = −27→27 |
9372 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C13H12N2O2 | V = 1094.2 (2) Å3 |
Mr = 228.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.5296 (6) Å | µ = 0.10 mm−1 |
b = 23.083 (3) Å | T = 293 K |
c = 9.3088 (9) Å | 0.25 × 0.20 × 0.18 mm |
β = 112.940 (5)° |
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 = 0.983 | Rint = 0.021 |
9372 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.19 e Å−3 |
1938 reflections | Δρmin = −0.26 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0335 (2) | 0.84645 (5) | 0.26085 (13) | 0.0165 (3) | |
C2 | 0.9577 (2) | 0.80281 (5) | 0.14829 (15) | 0.0217 (3) | |
H2 | 0.7904 | 0.8035 | 0.0696 | 0.026* | |
C3 | 1.1293 (3) | 0.75831 (6) | 0.15255 (17) | 0.0267 (3) | |
H3 | 1.0774 | 0.7298 | 0.0760 | 0.032* | |
C4 | 1.3792 (3) | 0.75629 (6) | 0.27120 (17) | 0.0271 (3) | |
H4 | 1.4942 | 0.7264 | 0.2746 | 0.033* | |
C5 | 1.4545 (2) | 0.79918 (6) | 0.38396 (15) | 0.0252 (3) | |
H5 | 1.6204 | 0.7979 | 0.4640 | 0.030* | |
C6 | 1.2845 (2) | 0.84412 (5) | 0.37859 (14) | 0.0206 (3) | |
H6 | 1.3385 | 0.8730 | 0.4543 | 0.025* | |
C7 | 0.8542 (2) | 0.89645 (5) | 0.25832 (13) | 0.0167 (3) | |
H7A | 0.7595 | 0.8869 | 0.3236 | 0.020* | |
H7B | 0.9601 | 0.9305 | 0.3022 | 0.020* | |
C8 | 0.7226 (2) | 0.94298 (5) | −0.00412 (13) | 0.0158 (3) | |
H8 | 0.8792 | 0.9627 | 0.0164 | 0.019* | |
C9 | 0.5118 (2) | 0.94220 (5) | −0.14451 (13) | 0.0152 (3) | |
C10 | 0.3150 (2) | 0.90594 (5) | −0.12295 (13) | 0.0162 (3) | |
C11 | 0.4214 (2) | 0.88767 (5) | 0.03064 (13) | 0.0171 (3) | |
H11 | 0.3383 | 0.8638 | 0.0779 | 0.021* | |
C12 | 0.5128 (2) | 0.97561 (5) | −0.28041 (13) | 0.0171 (3) | |
C13 | 0.0602 (2) | 0.88460 (5) | −0.22590 (14) | 0.0199 (3) | |
H13 | −0.0288 | 0.8620 | −0.1797 | 0.024* | |
N1 | 0.66548 (19) | 0.90998 (4) | 0.10118 (11) | 0.0152 (3) | |
N2 | 0.2915 (2) | 0.97471 (5) | −0.40897 (12) | 0.0214 (3) | |
H2A | 0.2825 | 0.9936 | −0.4906 | 0.026* | |
H2B | 0.1581 | 0.9553 | −0.4100 | 0.026* | |
O1 | 0.71039 (17) | 1.00283 (4) | −0.27249 (10) | 0.0237 (3) | |
O2 | −0.05271 (17) | 0.89275 (4) | −0.36651 (10) | 0.0255 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0178 (6) | 0.0173 (6) | 0.0150 (6) | −0.0021 (5) | 0.0072 (5) | 0.0043 (4) |
C2 | 0.0162 (6) | 0.0221 (7) | 0.0233 (7) | −0.0031 (5) | 0.0041 (5) | −0.0016 (5) |
C3 | 0.0249 (7) | 0.0193 (7) | 0.0347 (8) | −0.0027 (5) | 0.0103 (6) | −0.0052 (5) |
C4 | 0.0234 (7) | 0.0199 (7) | 0.0380 (8) | 0.0052 (5) | 0.0120 (6) | 0.0061 (5) |
C5 | 0.0181 (6) | 0.0284 (7) | 0.0244 (7) | 0.0026 (5) | 0.0033 (5) | 0.0086 (5) |
C6 | 0.0209 (6) | 0.0228 (7) | 0.0159 (6) | −0.0023 (5) | 0.0046 (5) | 0.0020 (5) |
C7 | 0.0167 (6) | 0.0198 (6) | 0.0113 (6) | −0.0003 (5) | 0.0029 (5) | 0.0011 (4) |
C8 | 0.0156 (6) | 0.0153 (6) | 0.0163 (6) | −0.0010 (4) | 0.0062 (5) | 0.0001 (4) |
C9 | 0.0160 (6) | 0.0142 (6) | 0.0147 (6) | 0.0013 (4) | 0.0051 (5) | −0.0014 (4) |
C10 | 0.0153 (6) | 0.0175 (6) | 0.0154 (6) | 0.0012 (5) | 0.0057 (5) | −0.0008 (4) |
C11 | 0.0155 (6) | 0.0183 (6) | 0.0185 (6) | −0.0017 (5) | 0.0076 (5) | 0.0004 (5) |
C12 | 0.0200 (6) | 0.0144 (6) | 0.0162 (6) | 0.0009 (5) | 0.0064 (5) | −0.0008 (4) |
C13 | 0.0171 (6) | 0.0221 (6) | 0.0194 (7) | −0.0005 (5) | 0.0059 (5) | −0.0007 (5) |
N1 | 0.0155 (5) | 0.0164 (5) | 0.0120 (5) | 0.0006 (4) | 0.0037 (4) | 0.0007 (4) |
N2 | 0.0198 (6) | 0.0265 (6) | 0.0149 (5) | −0.0022 (4) | 0.0034 (4) | 0.0055 (4) |
O1 | 0.0233 (5) | 0.0275 (5) | 0.0177 (5) | −0.0062 (4) | 0.0052 (4) | 0.0042 (3) |
O2 | 0.0213 (5) | 0.0314 (6) | 0.0178 (5) | −0.0034 (4) | 0.0009 (4) | −0.0008 (4) |
C1—C6 | 1.3942 (17) | C8—C9 | 1.3709 (16) |
C1—C2 | 1.3949 (18) | C8—N1 | 1.3719 (15) |
C1—C7 | 1.5159 (16) | C8—H8 | 0.9300 |
C2—C3 | 1.3886 (18) | C9—C10 | 1.4476 (16) |
C2—H2 | 0.9300 | C9—C12 | 1.4834 (16) |
C3—C4 | 1.3933 (19) | C10—C11 | 1.3829 (16) |
C3—H3 | 0.9300 | C10—C13 | 1.4471 (17) |
C4—C5 | 1.384 (2) | C11—N1 | 1.3516 (15) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.3877 (18) | C12—O1 | 1.2375 (15) |
C5—H5 | 0.9300 | C12—N2 | 1.3374 (16) |
C6—H6 | 0.9300 | C13—O2 | 1.2253 (15) |
C7—N1 | 1.4616 (14) | C13—H13 | 0.9300 |
C7—H7A | 0.9700 | N2—H2A | 0.8600 |
C7—H7B | 0.9700 | N2—H2B | 0.8600 |
C6—C1—C2 | 118.58 (11) | C9—C8—N1 | 109.08 (10) |
C6—C1—C7 | 119.09 (11) | C9—C8—H8 | 125.5 |
C2—C1—C7 | 122.33 (11) | N1—C8—H8 | 125.5 |
C3—C2—C1 | 120.71 (12) | C8—C9—C10 | 106.34 (10) |
C3—C2—H2 | 119.6 | C8—C9—C12 | 121.46 (11) |
C1—C2—H2 | 119.6 | C10—C9—C12 | 132.19 (11) |
C2—C3—C4 | 120.19 (12) | C11—C10—C13 | 119.54 (11) |
C2—C3—H3 | 119.9 | C11—C10—C9 | 106.24 (10) |
C4—C3—H3 | 119.9 | C13—C10—C9 | 134.08 (11) |
C5—C4—C3 | 119.32 (12) | N1—C11—C10 | 109.15 (10) |
C5—C4—H4 | 120.3 | N1—C11—H11 | 125.4 |
C3—C4—H4 | 120.3 | C10—C11—H11 | 125.4 |
C4—C5—C6 | 120.55 (12) | O1—C12—N2 | 122.68 (11) |
C4—C5—H5 | 119.7 | O1—C12—C9 | 120.65 (10) |
C6—C5—H5 | 119.7 | N2—C12—C9 | 116.67 (10) |
C5—C6—C1 | 120.65 (12) | O2—C13—C10 | 127.90 (12) |
C5—C6—H6 | 119.7 | O2—C13—H13 | 116.0 |
C1—C6—H6 | 119.7 | C10—C13—H13 | 116.0 |
N1—C7—C1 | 112.69 (9) | C11—N1—C8 | 109.20 (10) |
N1—C7—H7A | 109.1 | C11—N1—C7 | 126.38 (10) |
C1—C7—H7A | 109.1 | C8—N1—C7 | 124.07 (10) |
N1—C7—H7B | 109.1 | C12—N2—H2A | 120.0 |
C1—C7—H7B | 109.1 | C12—N2—H2B | 120.0 |
H7A—C7—H7B | 107.8 | H2A—N2—H2B | 120.0 |
C6—C1—C2—C3 | −0.61 (18) | C12—C9—C10—C13 | 6.5 (2) |
C7—C1—C2—C3 | 178.65 (11) | C13—C10—C11—N1 | 176.01 (10) |
C1—C2—C3—C4 | 0.9 (2) | C9—C10—C11—N1 | −0.30 (13) |
C2—C3—C4—C5 | −0.3 (2) | C8—C9—C12—O1 | 3.69 (18) |
C3—C4—C5—C6 | −0.6 (2) | C10—C9—C12—O1 | −178.07 (11) |
C4—C5—C6—C1 | 0.92 (19) | C8—C9—C12—N2 | −176.06 (10) |
C2—C1—C6—C5 | −0.30 (18) | C10—C9—C12—N2 | 2.19 (19) |
C7—C1—C6—C5 | −179.59 (11) | C11—C10—C13—O2 | −173.94 (12) |
C6—C1—C7—N1 | 151.87 (11) | C9—C10—C13—O2 | 1.1 (2) |
C2—C1—C7—N1 | −27.39 (15) | C10—C11—N1—C8 | 0.01 (13) |
N1—C8—C9—C10 | −0.47 (13) | C10—C11—N1—C7 | −173.30 (10) |
N1—C8—C9—C12 | 178.17 (10) | C9—C8—N1—C11 | 0.30 (13) |
C8—C9—C10—C11 | 0.47 (13) | C9—C8—N1—C7 | 173.80 (10) |
C12—C9—C10—C11 | −177.97 (12) | C1—C7—N1—C11 | 90.92 (13) |
C8—C9—C10—C13 | −175.05 (13) | C1—C7—N1—C8 | −81.44 (13) |
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. |
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. |
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) |
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 (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).
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