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access5-Chloro-1-phenyl-1H-tetrazole
aTianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
*Correspondence e-mail: hxxywy@mail.tjnu.edu.cn
The tetrazole and phenyl rings of the title compound, C7H5ClN4, form a dihedral angle 64.5°.
Related literature
For the ferroelectric properties of tetrazole derivatives, see: Sengupta & Mukherjee (2010![[Sengupta, O. & Mukherjee, P. S. (2010). Inorg. Chem. 49, 8583-8590.]](../../../../../../logos/arrows/e_arr.gif "Sengupta, O. & Mukherjee, P. S. (2010). Inorg. Chem. 49, 8583-8590.")
). For their magnetic properties, see: Grunert et al. (2004); Van Koningsbruggen et al. (2000). For their luminescent properties, see: Wang et al. (2005).
![[Scheme 1]](aa2009scheme1.gif)
Experimental
Crystal data
|
Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536811021210/aa2009sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811021210/aa2009Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811021210/aa2009Isup3.cml
5-Chloro-1-phenyl-1H-tetrazole (I) (54.18 mg, 0.3 mmol) was stirred for 0.5 h in H2O (5 ml) and CH3CN (5 ml). Upon slow evaporation of the filtrate at room temperatre for two weeks, well shaped colorless crystals suitable for X-ray diffraction were obtained. Yield: 90%. Elemental analysis calcd (%) for (I): C 46.55, H 2.79, N 31.02%; found: C 46.26, H 2.68, N 31.37%.
H atoms were introduced in their idealized positions and refined as riding with C—H 0.93 Å.
Data collection: SMART (Bruker, 1998); cell SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./aa2009fig1thm.gif) | Fig. 1. A view of (I), with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are drawn as circles. |
| C7H5ClN4 | F(000) = 368 |
| Mr = 180.60 | Dx = 1.519 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1689 reflections |
| a = 7.0428 (7) Å | θ = 3.0–27.2° |
| b = 6.4150 (6) Å | µ = 0.43 mm−1 |
| c = 17.5804 (18) Å | T = 296 K |
| β = 96.160 (2)° | Block, colourless |
| V = 789.69 (13) Å3 | 0.15 × 0.14 × 0.13 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 1404 independent reflections |
| Radiation source: fine-focus sealed tube | 1176 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.014 |
| ϕ and ω scans | θmax = 25.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −5→8 |
| Tmin = 0.939, Tmax = 0.947 | k = −7→7 |
| 3879 measured reflections | l = −20→20 |
| 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.092 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1635P] where P = (Fo2 + 2Fc2)/3 |
| 1404 reflections | (Δ/σ)max < 0.001 |
| 109 parameters | Δρmax = 0.12 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
| C7H5ClN4 | V = 789.69 (13) Å3 |
| Mr = 180.60 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 7.0428 (7) Å | µ = 0.43 mm−1 |
| b = 6.4150 (6) Å | T = 296 K |
| c = 17.5804 (18) Å | 0.15 × 0.14 × 0.13 mm |
| β = 96.160 (2)° |
| Bruker SMART CCD area-detector diffractometer | 1404 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 1176 reflections with I > 2σ(I) |
| Tmin = 0.939, Tmax = 0.947 | Rint = 0.014 |
| 3879 measured reflections |
| R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
| wR(F2) = 0.092 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.12 e Å−3 |
| 1404 reflections | Δρmin = −0.26 e Å−3 |
| 109 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | ||
| Cl1 | 0.15030 (6) | 0.26017 (7) | 0.03941 (3) | 0.05392 (19) | |
| N1 | 0.5232 (2) | 0.25483 (17) | 0.08796 (8) | 0.0387 (3) | |
| N2 | 0.4612 (3) | 0.24646 (19) | −0.03563 (9) | 0.0527 (4) | |
| N3 | 0.6525 (3) | 0.2414 (2) | −0.01533 (10) | 0.0558 (4) | |
| N4 | 0.6930 (2) | 0.24610 (19) | 0.05813 (10) | 0.0504 (4) | |
| C1 | 0.3852 (3) | 0.2547 (2) | 0.02910 (10) | 0.0416 (4) | |
| C2 | 0.5109 (2) | 0.2662 (2) | 0.16905 (9) | 0.0417 (4) | |
| C3 | 0.4356 (2) | 0.4431 (3) | 0.19789 (9) | 0.0505 (4) | |
| H3 | 0.3949 | 0.5534 | 0.1659 | 0.061* | |
| C4 | 0.4216 (3) | 0.4538 (4) | 0.27567 (10) | 0.0646 (6) | |
| H4 | 0.3699 | 0.5716 | 0.2963 | 0.078* | |
| C5 | 0.4836 (3) | 0.2919 (4) | 0.32218 (11) | 0.0709 (7) | |
| H5 | 0.4740 | 0.3003 | 0.3744 | 0.085* | |
| C6 | 0.5600 (3) | 0.1167 (4) | 0.29252 (11) | 0.0725 (6) | |
| H6 | 0.6029 | 0.0080 | 0.3249 | 0.087* | |
| C7 | 0.5737 (2) | 0.1004 (3) | 0.21435 (10) | 0.0570 (5) | |
| H7 | 0.6235 | −0.0183 | 0.1936 | 0.068* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0445 (3) | 0.0682 (3) | 0.0478 (3) | −0.00030 (19) | −0.0010 (2) | 0.00150 (18) |
| N1 | 0.0380 (7) | 0.0418 (7) | 0.0376 (7) | 0.0000 (5) | 0.0103 (6) | −0.0016 (5) |
| N2 | 0.0734 (11) | 0.0471 (9) | 0.0396 (8) | −0.0045 (7) | 0.0160 (8) | −0.0009 (6) |
| N3 | 0.0706 (11) | 0.0479 (9) | 0.0542 (10) | −0.0037 (7) | 0.0309 (8) | −0.0039 (6) |
| N4 | 0.0477 (8) | 0.0495 (8) | 0.0577 (10) | −0.0012 (6) | 0.0218 (7) | −0.0035 (6) |
| C1 | 0.0509 (10) | 0.0367 (8) | 0.0380 (9) | −0.0018 (6) | 0.0083 (8) | 0.0009 (6) |
| C2 | 0.0345 (8) | 0.0559 (10) | 0.0350 (8) | −0.0008 (7) | 0.0052 (7) | 0.0007 (6) |
| C3 | 0.0512 (10) | 0.0596 (11) | 0.0411 (9) | 0.0060 (8) | 0.0069 (7) | −0.0032 (8) |
| C4 | 0.0580 (12) | 0.0918 (15) | 0.0448 (10) | 0.0055 (10) | 0.0089 (9) | −0.0151 (10) |
| C5 | 0.0493 (11) | 0.128 (2) | 0.0349 (10) | −0.0011 (12) | 0.0031 (8) | 0.0015 (11) |
| C6 | 0.0518 (12) | 0.1107 (18) | 0.0532 (11) | 0.0097 (12) | −0.0020 (9) | 0.0329 (12) |
| C7 | 0.0463 (10) | 0.0684 (12) | 0.0567 (11) | 0.0117 (8) | 0.0077 (8) | 0.0134 (9) |
| Cl1—C1 | 1.6841 (18) | C3—C4 | 1.383 (2) |
| N1—C1 | 1.341 (2) | C3—H3 | 0.9300 |
| N1—N4 | 1.357 (2) | C4—C5 | 1.364 (3) |
| N1—C2 | 1.439 (2) | C4—H4 | 0.9300 |
| N2—C1 | 1.309 (2) | C5—C6 | 1.373 (3) |
| N2—N3 | 1.357 (3) | C5—H5 | 0.9300 |
| N3—N4 | 1.293 (2) | C6—C7 | 1.392 (3) |
| C2—C3 | 1.373 (2) | C6—H6 | 0.9300 |
| C2—C7 | 1.373 (2) | C7—H7 | 0.9300 |
| C1—N1—N4 | 107.28 (15) | C4—C3—H3 | 120.7 |
| C1—N1—C2 | 130.44 (14) | C5—C4—C3 | 120.20 (19) |
| N4—N1—C2 | 122.27 (14) | C5—C4—H4 | 119.9 |
| C1—N2—N3 | 105.02 (16) | C3—C4—H4 | 119.9 |
| N4—N3—N2 | 111.63 (15) | C4—C5—C6 | 120.57 (18) |
| N3—N4—N1 | 106.14 (16) | C4—C5—H5 | 119.7 |
| N2—C1—N1 | 109.93 (17) | C6—C5—H5 | 119.7 |
| N2—C1—Cl1 | 126.31 (16) | C5—C6—C7 | 120.52 (18) |
| N1—C1—Cl1 | 123.75 (14) | C5—C6—H6 | 119.7 |
| C3—C2—C7 | 122.63 (16) | C7—C6—H6 | 119.7 |
| C3—C2—N1 | 118.32 (14) | C2—C7—C6 | 117.56 (18) |
| C7—C2—N1 | 119.05 (14) | C2—C7—H7 | 121.2 |
| C2—C3—C4 | 118.51 (17) | C6—C7—H7 | 121.2 |
| C2—C3—H3 | 120.7 | ||
| C1—N2—N3—N4 | 0.03 (16) | N4—N1—C2—C3 | 115.00 (16) |
| N2—N3—N4—N1 | −0.05 (16) | C1—N1—C2—C7 | 116.21 (18) |
| C1—N1—N4—N3 | 0.04 (15) | N4—N1—C2—C7 | −65.26 (19) |
| C2—N1—N4—N3 | −178.79 (12) | C7—C2—C3—C4 | −0.4 (3) |
| N3—N2—C1—N1 | −0.01 (15) | N1—C2—C3—C4 | 179.32 (15) |
| N3—N2—C1—Cl1 | −178.96 (11) | C2—C3—C4—C5 | 0.7 (3) |
| N4—N1—C1—N2 | −0.02 (16) | C3—C4—C5—C6 | −0.1 (3) |
| C2—N1—C1—N2 | 178.68 (13) | C4—C5—C6—C7 | −0.7 (3) |
| N4—N1—C1—Cl1 | 178.96 (10) | C3—C2—C7—C6 | −0.4 (3) |
| C2—N1—C1—Cl1 | −2.3 (2) | N1—C2—C7—C6 | 179.91 (16) |
| C1—N1—C2—C3 | −63.5 (2) | C5—C6—C7—C2 | 0.9 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C7H5ClN4 |
| Mr | 180.60 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c (Å) | 7.0428 (7), 6.4150 (6), 17.5804 (18) |
| β (°) | 96.160 (2) |
| V (Å3) | 789.69 (13) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.43 |
| Crystal size (mm) | 0.15 × 0.14 × 0.13 |
| Data collection | |
| Diffractometer | Bruker SMART CCD area-detector diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
| Tmin, Tmax | 0.939, 0.947 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3879, 1404, 1176 |
| Rint | 0.014 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.092, 1.05 |
| No. of reflections | 1404 |
| No. of parameters | 109 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.12, −0.26 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported financially by Tianjin Normal University (grant No. 5RL090), the Natural Science Foundation of Tianjin (grant No. 11JCYBJC03600) and the Young Scientist Fund (grant No. 52 G10005).
References
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Sengupta, O. & Mukherjee, P. S. (2010). Inorg. Chem. 49, 8583–8590. Web of Science CrossRef CAS PubMed Google Scholar
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The design and synthesis of new tetrazole derivatives have attracted much interest owing to their ferroecletric (Sengupta & Mukherjee, 2010), luminescent (Wang et al., 2005) and magnetic properties (Grunert et al., 2004; Van Koningsbruggen et al., 2000). The crystal structure of 5-chloro-1-phenyl-1H-tetrazole (I) is shown in Fig. 1.