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access(1H-1,2,3-Benzotriazol-1-yl)methyl benzoate
aDepartment of Stomatology, Nanjing Jinling Hospital, Nanjing University School of Medicine, 305, East Zhongshan Road, 210002 Nanjing, Jiangsu Province, People's Republic of China, and bDepartment of Applied Chemistry, School of Material Science and Engineering, Nanjing University of Aeronautics and Astronautics, Nanjing, Jiangsu Province 210016, People's Republic of China
*Correspondence e-mail: caogang69@163.com
In the title compound, C14H11N3O2, the dihedral angle between the phenyl ring and the benzotriazole ring system is 76.80 (19)° and the molecule has an L-shaped conformation. In the crystal, weak aromatic π–π stacking is observed, the closest centroid–centroid distance being 3.754 (2) Å.
Related literature
For related structures and the synthesis, see: Xu & Shen (2012)![[Xu, S. & Shen, Y. (2012). Acta Cryst. E68, o1066.]](../../../../../../logos/arrows/e_arr.gif "Xu, S. & Shen, Y. (2012). Acta Cryst. E68, o1066.")
; Zeng & Jian (2009). For applications of benzotriazole derivatives, see: Wan & Lv (2010).
![[Scheme 1]](hb6707scheme1.gif)
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536812015140/hb6707sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536812015140/hb6707Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812015140/hb6707Isup3.cml
The title compound synthesis method is similar to that reported by Xu & Shen (2012), but methylene chloride was replaced by benzoyl chloride
The H atoms on the CH2 group were located by difference maps and freely refined without constraints. H atoms bonded to the remaining C atoms were included in calculated positions and treated as riding with C–H =0.93Å and Uiso(H)=1.2Ueq(aromatic C).
Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hb6707fig1thm.gif) | Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. |
| C14H11N3O2 | F(000) = 528 |
| Mr = 253.26 | Dx = 1.303 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1419 reflections |
| a = 10.7181 (4) Å | θ = 2.7–21.6° |
| b = 6.4826 (2) Å | µ = 0.09 mm−1 |
| c = 18.7076 (7) Å | T = 296 K |
| β = 96.773 (3)° | Block, colorless |
| V = 1290.75 (8) Å3 | 0.20 × 0.20 × 0.18 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 2268 independent reflections |
| Radiation source: fine-focus sealed tube | 1352 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.057 |
| Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
| phi and ω scans | h = −12→12 |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | k = −7→7 |
| Tmin = 0.982, Tmax = 0.984 | l = −22→22 |
| 9412 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.4539P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 2268 reflections | Δρmax = 0.14 e Å−3 |
| 181 parameters | Δρmin = −0.17 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0073 (18) |
| C14H11N3O2 | V = 1290.75 (8) Å3 |
| Mr = 253.26 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.7181 (4) Å | µ = 0.09 mm−1 |
| b = 6.4826 (2) Å | T = 296 K |
| c = 18.7076 (7) Å | 0.20 × 0.20 × 0.18 mm |
| β = 96.773 (3)° |
| Bruker SMART CCD diffractometer | 2268 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1352 reflections with I > 2σ(I) |
| Tmin = 0.982, Tmax = 0.984 | Rint = 0.057 |
| 9412 measured reflections |
| R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
| wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | Δρmax = 0.14 e Å−3 |
| 2268 reflections | Δρmin = −0.17 e Å−3 |
| 181 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
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 > 2sigma(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 | 0.7169 (3) | 0.5849 (5) | 0.27655 (16) | 0.0599 (8) | |
| C2 | 0.8234 (3) | 0.7177 (6) | 0.30445 (18) | 0.0672 (9) | |
| C3 | 0.9100 (4) | 0.6382 (8) | 0.3586 (2) | 0.1029 (14) | |
| H3 | 0.8998 | 0.5062 | 0.3765 | 0.123* | |
| C4 | 1.0110 (5) | 0.7578 (13) | 0.3853 (3) | 0.145 (2) | |
| H4 | 1.0696 | 0.7062 | 0.4215 | 0.174* | |
| C5 | 1.0258 (6) | 0.9545 (14) | 0.3586 (4) | 0.157 (3) | |
| H5 | 1.0944 | 1.0342 | 0.3769 | 0.189* | |
| C6 | 0.9397 (5) | 1.0320 (8) | 0.3054 (3) | 0.1179 (18) | |
| H6 | 0.9497 | 1.1645 | 0.2878 | 0.141* | |
| C7 | 0.8391 (3) | 0.9146 (6) | 0.2781 (2) | 0.0814 (11) | |
| H7 | 0.7810 | 0.9671 | 0.2418 | 0.098* | |
| C8 | 0.5351 (3) | 0.5700 (6) | 0.19118 (18) | 0.0614 (9) | |
| C9 | 0.6278 (3) | 0.2459 (5) | 0.05103 (16) | 0.0564 (8) | |
| C10 | 0.6200 (3) | 0.4440 (4) | 0.07805 (14) | 0.0505 (7) | |
| C11 | 0.6600 (3) | 0.6164 (5) | 0.04401 (16) | 0.0608 (9) | |
| H11 | 0.6543 | 0.7485 | 0.0628 | 0.073* | |
| C12 | 0.7088 (3) | 0.5800 (5) | −0.01930 (17) | 0.0726 (10) | |
| H12 | 0.7380 | 0.6911 | −0.0441 | 0.087* | |
| C13 | 0.7165 (3) | 0.3815 (6) | −0.04810 (17) | 0.0724 (10) | |
| H13 | 0.7504 | 0.3649 | −0.0913 | 0.087* | |
| C14 | 0.6758 (3) | 0.2130 (5) | −0.01465 (17) | 0.0686 (9) | |
| H14 | 0.6796 | 0.0817 | −0.0343 | 0.082* | |
| H1M | 0.482 (3) | 0.679 (5) | 0.1671 (18) | 0.078 (11)* | |
| H2M | 0.491 (3) | 0.493 (5) | 0.2271 (18) | 0.087 (11)* | |
| N1 | 0.5679 (2) | 0.4166 (4) | 0.14069 (12) | 0.0571 (7) | |
| N2 | 0.5446 (3) | 0.2141 (4) | 0.15102 (14) | 0.0729 (8) | |
| N3 | 0.5796 (3) | 0.1092 (4) | 0.09718 (15) | 0.0752 (9) | |
| O1 | 0.64454 (19) | 0.6783 (3) | 0.22152 (10) | 0.0584 (6) | |
| O2 | 0.6951 (2) | 0.4154 (4) | 0.29774 (13) | 0.0830 (8) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.065 (2) | 0.067 (2) | 0.0494 (17) | 0.0088 (18) | 0.0141 (16) | 0.0005 (16) |
| C2 | 0.055 (2) | 0.090 (3) | 0.057 (2) | −0.0006 (19) | 0.0115 (17) | −0.0160 (19) |
| C3 | 0.071 (3) | 0.155 (4) | 0.080 (3) | 0.016 (3) | −0.003 (2) | −0.014 (3) |
| C4 | 0.075 (4) | 0.240 (8) | 0.114 (5) | 0.002 (5) | −0.015 (3) | −0.043 (5) |
| C5 | 0.075 (4) | 0.228 (8) | 0.170 (7) | −0.039 (5) | 0.018 (4) | −0.089 (7) |
| C6 | 0.085 (3) | 0.125 (4) | 0.152 (5) | −0.041 (3) | 0.050 (3) | −0.057 (4) |
| C7 | 0.072 (3) | 0.089 (3) | 0.088 (3) | −0.018 (2) | 0.030 (2) | −0.026 (2) |
| C8 | 0.061 (2) | 0.070 (2) | 0.0534 (19) | 0.0043 (19) | 0.0083 (18) | −0.0129 (18) |
| C9 | 0.064 (2) | 0.0560 (17) | 0.0497 (17) | 0.0003 (15) | 0.0079 (16) | −0.0034 (14) |
| C10 | 0.0551 (19) | 0.0539 (17) | 0.0423 (15) | 0.0009 (14) | 0.0045 (14) | −0.0016 (13) |
| C11 | 0.076 (2) | 0.0547 (18) | 0.0516 (17) | −0.0021 (16) | 0.0078 (17) | −0.0012 (14) |
| C12 | 0.085 (3) | 0.079 (2) | 0.0553 (19) | −0.0057 (19) | 0.0155 (19) | 0.0080 (18) |
| C13 | 0.081 (3) | 0.092 (3) | 0.0465 (18) | 0.006 (2) | 0.0182 (17) | −0.0043 (18) |
| C14 | 0.081 (2) | 0.070 (2) | 0.0552 (19) | 0.0090 (18) | 0.0105 (18) | −0.0145 (17) |
| N1 | 0.0712 (18) | 0.0564 (15) | 0.0454 (13) | 0.0007 (13) | 0.0136 (13) | −0.0026 (12) |
| N2 | 0.103 (2) | 0.0594 (17) | 0.0583 (17) | −0.0114 (15) | 0.0191 (16) | −0.0007 (14) |
| N3 | 0.110 (2) | 0.0569 (16) | 0.0611 (17) | −0.0071 (15) | 0.0225 (17) | −0.0055 (14) |
| O1 | 0.0718 (15) | 0.0583 (12) | 0.0450 (11) | −0.0001 (11) | 0.0064 (11) | −0.0033 (10) |
| O2 | 0.0905 (19) | 0.0774 (16) | 0.0804 (17) | 0.0015 (13) | 0.0077 (14) | 0.0232 (13) |
| C1—O2 | 1.200 (3) | C8—H1M | 0.98 (3) |
| C1—O1 | 1.356 (3) | C8—H2M | 1.00 (3) |
| C1—C2 | 1.476 (5) | C9—N3 | 1.379 (4) |
| C2—C7 | 1.385 (5) | C9—C10 | 1.386 (4) |
| C2—C3 | 1.389 (5) | C9—C14 | 1.404 (4) |
| C3—C4 | 1.377 (7) | C10—N1 | 1.367 (3) |
| C3—H3 | 0.9300 | C10—C11 | 1.380 (4) |
| C4—C5 | 1.385 (9) | C11—C12 | 1.371 (4) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.371 (8) | C12—C13 | 1.401 (4) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C6—C7 | 1.369 (6) | C13—C14 | 1.357 (4) |
| C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| C7—H7 | 0.9300 | C14—H14 | 0.9300 |
| C8—O1 | 1.426 (4) | N1—N2 | 1.355 (3) |
| C8—N1 | 1.443 (4) | N2—N3 | 1.306 (3) |
| O2—C1—O1 | 122.9 (3) | H1M—C8—H2M | 112 (3) |
| O2—C1—C2 | 126.1 (3) | N3—C9—C10 | 108.9 (3) |
| O1—C1—C2 | 111.0 (3) | N3—C9—C14 | 130.8 (3) |
| C7—C2—C3 | 120.2 (4) | C10—C9—C14 | 120.3 (3) |
| C7—C2—C1 | 122.2 (3) | N1—C10—C11 | 133.0 (3) |
| C3—C2—C1 | 117.6 (4) | N1—C10—C9 | 103.9 (2) |
| C4—C3—C2 | 119.0 (5) | C11—C10—C9 | 123.1 (3) |
| C4—C3—H3 | 120.5 | C12—C11—C10 | 115.5 (3) |
| C2—C3—H3 | 120.5 | C12—C11—H11 | 122.3 |
| C3—C4—C5 | 120.4 (7) | C10—C11—H11 | 122.3 |
| C3—C4—H4 | 119.8 | C11—C12—C13 | 122.4 (3) |
| C5—C4—H4 | 119.8 | C11—C12—H12 | 118.8 |
| C6—C5—C4 | 120.2 (7) | C13—C12—H12 | 118.8 |
| C6—C5—H5 | 119.9 | C14—C13—C12 | 121.7 (3) |
| C4—C5—H5 | 119.9 | C14—C13—H13 | 119.1 |
| C7—C6—C5 | 120.0 (6) | C12—C13—H13 | 119.1 |
| C7—C6—H6 | 120.0 | C13—C14—C9 | 116.9 (3) |
| C5—C6—H6 | 120.0 | C13—C14—H14 | 121.6 |
| C6—C7—C2 | 120.2 (5) | C9—C14—H14 | 121.6 |
| C6—C7—H7 | 119.9 | N2—N1—C10 | 110.4 (2) |
| C2—C7—H7 | 119.9 | N2—N1—C8 | 120.7 (3) |
| O1—C8—N1 | 110.3 (3) | C10—N1—C8 | 128.8 (3) |
| O1—C8—H1M | 103.6 (18) | N3—N2—N1 | 108.6 (2) |
| N1—C8—H1M | 111.5 (19) | N2—N3—C9 | 108.1 (2) |
| O1—C8—H2M | 114.3 (19) | C1—O1—C8 | 116.9 (3) |
| N1—C8—H2M | 105.7 (19) | ||
| O2—C1—C2—C7 | −177.9 (3) | C11—C12—C13—C14 | −0.1 (6) |
| O1—C1—C2—C7 | 3.0 (4) | C12—C13—C14—C9 | −1.2 (5) |
| O2—C1—C2—C3 | 2.5 (5) | N3—C9—C14—C13 | 179.8 (3) |
| O1—C1—C2—C3 | −176.6 (3) | C10—C9—C14—C13 | 1.9 (5) |
| C7—C2—C3—C4 | −0.1 (6) | C11—C10—N1—N2 | −180.0 (3) |
| C1—C2—C3—C4 | 179.5 (4) | C9—C10—N1—N2 | −0.4 (3) |
| C2—C3—C4—C5 | 0.1 (8) | C11—C10—N1—C8 | 1.9 (6) |
| C3—C4—C5—C6 | 0.1 (10) | C9—C10—N1—C8 | −178.5 (3) |
| C4—C5—C6—C7 | −0.4 (9) | O1—C8—N1—N2 | 119.7 (3) |
| C5—C6—C7—C2 | 0.4 (6) | O1—C8—N1—C10 | −62.3 (4) |
| C3—C2—C7—C6 | −0.1 (5) | C10—N1—N2—N3 | −0.1 (4) |
| C1—C2—C7—C6 | −179.7 (3) | C8—N1—N2—N3 | 178.3 (3) |
| N3—C9—C10—N1 | 0.7 (3) | N1—N2—N3—C9 | 0.5 (4) |
| C14—C9—C10—N1 | 179.0 (3) | C10—C9—N3—N2 | −0.8 (4) |
| N3—C9—C10—C11 | −179.7 (3) | C14—C9—N3—N2 | −178.9 (3) |
| C14—C9—C10—C11 | −1.3 (5) | O2—C1—O1—C8 | 3.2 (4) |
| N1—C10—C11—C12 | 179.6 (3) | C2—C1—O1—C8 | −177.7 (2) |
| C9—C10—C11—C12 | 0.0 (5) | N1—C8—O1—C1 | −81.1 (3) |
| C10—C11—C12—C13 | 0.7 (5) |
Experimental details
| Crystal data | |
| Chemical formula | C14H11N3O2 |
| Mr | 253.26 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 296 |
| a, b, c (Å) | 10.7181 (4), 6.4826 (2), 18.7076 (7) |
| β (°) | 96.773 (3) |
| V (Å3) | 1290.75 (8) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.20 × 0.20 × 0.18 |
| Data collection | |
| Diffractometer | Bruker SMART CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
| Tmin, Tmax | 0.982, 0.984 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 9412, 2268, 1352 |
| Rint | 0.057 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.162, 1.06 |
| No. of reflections | 2268 |
| No. of parameters | 181 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.14, −0.17 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the Surface Project Foundation of Nanjing Military Region (10MA095), the Jinling Hospital Foundation of Nanjing Province of China (2009Q021) and the Surface Project Foundation of Nanjing Military Region (11MA099).
References
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan, J. & Lv, P.-C. (2010). J. Chem. Inf. Comput. Sci. 122, 597–606. CAS Google Scholar
Xu, S. & Shen, Y. (2012). Acta Cryst. E68, o1066. CSD CrossRef IUCr Journals Google Scholar
Zeng, W.-L. & Jian, F.-F. (2009). Acta Cryst. E65, o2165. Web of Science CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Benzotriazole derivatives have been broadly researched due to their potential applications (Wan & Lv, 2010). Herein, we have synthesized a new benzotriazole derivative(Fig. 1), C12H15N3O2. Bond lengths and angles are comparable to other reported benzotriazol-1-yl intermediate derivatives (Zeng & Jian, 2009; Xu & Shen, 2012). Furthermore, the dihedral angle between the mean planes of the phenyl and benzotriazole rings is 76.80 (19)°. In the crystal, π–π stacking is observed between the inversion related phenyl rings of benzotriazolyl, the closest centroid-centroid distance being 3.754 (2)Å.