organic compounds
[2-(4-Chlorophenyl)-1,3-selenazol-4-yl]methanol
aShandong Provincial Key Laboratory of Chemical Energy Storage, and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: jchcui@163.com
In the title compound, C10H8ClNOSe, the dihedral angle between benzene and selenazole rings is 11.4 (3)° and the hydroxymethyl group is bent from the selenazole ring, making a dihedral angle of 63.8 (3)°. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯N hydrogen bonds. Roof-tile-like stacking of the molecules along [010] [b = 4.5707 (4) Å] is observed, with the benzene and selenazole rings separated by a face-to-face distance of 3.57 Å and a mutual slippage of 2.85 Å.
Related literature
For the synthesis of 1,3-selenazoles and their biological activity, see: Shafiee et al. (1979); Koketsu & Ishihara (2003); Geisler et al. (2004). For crystal structures of 1,3-selenazole derivatives, see: Shen et al. (2011); Shi & Zhao, (2007).
Experimental
Crystal data
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Refinement
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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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812048088/qk2047sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048088/qk2047Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048088/qk2047Isup3.cml
2-(4-Chlorophenyl)-4-chloromethyl-1,3-selenazole (0.01 mol) (Shafiee et al., 1979) was added to dilute sulfuric acid (75 ml, 3.5 mol L-1) and heated at reflux for 8 h. The solution was made alkaline with dilute sodium hydroxide and extracted with chloroform. The organic layer was dried with Na2SO4, filtered, and evaporated and the obtained solid was recrystallized from ethanol. Clear block-shaped crystals were obtained.
C-bonded H atoms were placed in calculated positions and thereafter treated as riding, C—H = 0.93 and 0.97 Å, Uiso(H) = 1.2Ueq(C). The hydroxyl H atom was refined with AFIX 147 of program SHELXL97 (Sheldrick, 2008), O—H = 0.82 Å, Uĩso(H) = 1.5Ueq(O).
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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H8ClNOSe | F(000) = 536 |
Mr = 272.58 | Dx = 1.805 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1928 reflections |
a = 14.8150 (15) Å | θ = 2.8–27.1° |
b = 4.5707 (4) Å | µ = 3.97 mm−1 |
c = 14.9123 (14) Å | T = 298 K |
β = 96.642 (1)° | Block, white |
V = 1003.01 (16) Å3 | 0.35 × 0.32 × 0.15 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 1742 independent reflections |
Radiation source: fine-focus sealed tube | 1318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
π and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −15→17 |
Tmin = 0.337, Tmax = 0.587 | k = −5→5 |
4466 measured reflections | l = −17→14 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3 |
1742 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C10H8ClNOSe | V = 1003.01 (16) Å3 |
Mr = 272.58 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.8150 (15) Å | µ = 3.97 mm−1 |
b = 4.5707 (4) Å | T = 298 K |
c = 14.9123 (14) Å | 0.35 × 0.32 × 0.15 mm |
β = 96.642 (1)° |
Bruker SMART APEX CCD diffractometer | 1742 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1318 reflections with I > 2σ(I) |
Tmin = 0.337, Tmax = 0.587 | Rint = 0.059 |
4466 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.45 e Å−3 |
1742 reflections | Δρmin = −0.45 e Å−3 |
128 parameters |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.74166 (3) | 0.13939 (10) | 0.30636 (3) | 0.0423 (2) | |
Cl1 | 0.93843 (9) | 1.0498 (3) | 0.66855 (9) | 0.0586 (4) | |
O1 | 0.4348 (2) | −0.0090 (8) | 0.3910 (2) | 0.0465 (8) | |
H1 | 0.4149 | −0.0297 | 0.4396 | 0.070* | |
N1 | 0.6330 (2) | 0.1313 (7) | 0.4388 (2) | 0.0313 (8) | |
C1 | 0.8698 (3) | 0.8234 (9) | 0.5942 (3) | 0.0394 (11) | |
C2 | 0.7838 (3) | 0.7563 (10) | 0.6124 (3) | 0.0401 (11) | |
H2 | 0.7612 | 0.8350 | 0.6628 | 0.048* | |
C3 | 0.7307 (3) | 0.5702 (9) | 0.5551 (3) | 0.0352 (10) | |
H3 | 0.6722 | 0.5232 | 0.5672 | 0.042* | |
C4 | 0.7644 (3) | 0.4523 (9) | 0.4790 (2) | 0.0308 (10) | |
C5 | 0.8507 (3) | 0.5313 (11) | 0.4624 (3) | 0.0410 (11) | |
H5 | 0.8735 | 0.4589 | 0.4112 | 0.049* | |
C6 | 0.9042 (4) | 0.7147 (11) | 0.5196 (3) | 0.0503 (13) | |
H6 | 0.9626 | 0.7637 | 0.5078 | 0.060* | |
C7 | 0.7083 (3) | 0.2511 (9) | 0.4200 (2) | 0.0285 (9) | |
C8 | 0.6372 (3) | −0.0813 (9) | 0.2973 (3) | 0.0373 (11) | |
H8 | 0.6171 | −0.1989 | 0.2481 | 0.045* | |
C9 | 0.5933 (3) | −0.0506 (9) | 0.3712 (2) | 0.0293 (9) | |
C10 | 0.5071 (3) | −0.2087 (10) | 0.3850 (3) | 0.0410 (11) | |
H10A | 0.4912 | −0.3417 | 0.3349 | 0.049* | |
H10B | 0.5167 | −0.3236 | 0.4399 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0457 (4) | 0.0490 (4) | 0.0337 (3) | −0.0017 (2) | 0.0118 (2) | −0.0033 (2) |
Cl1 | 0.0543 (9) | 0.0538 (9) | 0.0629 (8) | −0.0135 (6) | −0.0131 (6) | −0.0081 (6) |
O1 | 0.037 (2) | 0.060 (2) | 0.0427 (18) | 0.0018 (18) | 0.0058 (15) | 0.0102 (16) |
N1 | 0.034 (2) | 0.029 (2) | 0.0299 (17) | 0.0012 (16) | −0.0013 (15) | −0.0014 (14) |
C1 | 0.042 (3) | 0.031 (3) | 0.042 (2) | −0.002 (2) | −0.008 (2) | 0.0014 (19) |
C2 | 0.049 (3) | 0.037 (3) | 0.034 (2) | −0.008 (2) | 0.005 (2) | −0.0008 (19) |
C3 | 0.027 (3) | 0.041 (3) | 0.039 (2) | −0.004 (2) | 0.0053 (19) | 0.0034 (19) |
C4 | 0.035 (3) | 0.029 (2) | 0.028 (2) | 0.0021 (19) | 0.0035 (18) | 0.0047 (16) |
C5 | 0.027 (3) | 0.046 (3) | 0.052 (3) | −0.002 (2) | 0.013 (2) | −0.009 (2) |
C6 | 0.036 (3) | 0.047 (3) | 0.069 (3) | −0.004 (2) | 0.010 (3) | −0.005 (3) |
C7 | 0.030 (3) | 0.029 (2) | 0.0265 (19) | 0.0094 (19) | 0.0022 (17) | 0.0039 (17) |
C8 | 0.040 (3) | 0.039 (3) | 0.032 (2) | 0.004 (2) | −0.0018 (19) | −0.0006 (18) |
C9 | 0.027 (2) | 0.029 (2) | 0.030 (2) | 0.0053 (18) | −0.0034 (18) | 0.0012 (17) |
C10 | 0.042 (3) | 0.039 (3) | 0.039 (2) | −0.007 (2) | −0.004 (2) | −0.002 (2) |
Se1—C8 | 1.839 (5) | C3—H3 | 0.9300 |
Se1—C7 | 1.889 (4) | C4—C5 | 1.378 (6) |
Cl1—C1 | 1.753 (4) | C4—C7 | 1.463 (6) |
O1—C10 | 1.419 (6) | C5—C6 | 1.380 (6) |
O1—H1 | 0.8200 | C5—H5 | 0.9300 |
N1—C7 | 1.303 (5) | C6—H6 | 0.9300 |
N1—C9 | 1.383 (5) | C8—C9 | 1.350 (6) |
C1—C2 | 1.367 (6) | C8—H8 | 0.9300 |
C1—C6 | 1.370 (6) | C9—C10 | 1.502 (6) |
C2—C3 | 1.385 (6) | C10—H10A | 0.9700 |
C2—H2 | 0.9300 | C10—H10B | 0.9700 |
C3—C4 | 1.399 (5) | ||
C8—Se1—C7 | 84.78 (19) | C1—C6—C5 | 118.8 (5) |
C10—O1—H1 | 109.5 | C1—C6—H6 | 120.6 |
C7—N1—C9 | 113.5 (4) | C5—C6—H6 | 120.6 |
C2—C1—C6 | 121.5 (4) | N1—C7—C4 | 125.2 (4) |
C2—C1—Cl1 | 119.6 (4) | N1—C7—Se1 | 113.5 (3) |
C6—C1—Cl1 | 118.9 (4) | C4—C7—Se1 | 121.3 (3) |
C1—C2—C3 | 119.5 (4) | C9—C8—Se1 | 111.3 (3) |
C1—C2—H2 | 120.3 | C9—C8—H8 | 124.3 |
C3—C2—H2 | 120.3 | Se1—C8—H8 | 124.3 |
C2—C3—C4 | 120.4 (4) | C8—C9—N1 | 116.9 (4) |
C2—C3—H3 | 119.8 | C8—C9—C10 | 123.9 (4) |
C4—C3—H3 | 119.8 | N1—C9—C10 | 119.1 (4) |
C5—C4—C3 | 118.1 (4) | O1—C10—C9 | 111.1 (4) |
C5—C4—C7 | 122.0 (4) | O1—C10—H10A | 109.4 |
C3—C4—C7 | 119.9 (4) | C9—C10—H10A | 109.4 |
C6—C5—C4 | 121.8 (4) | O1—C10—H10B | 109.4 |
C6—C5—H5 | 119.1 | C9—C10—H10B | 109.4 |
C4—C5—H5 | 119.1 | H10A—C10—H10B | 108.0 |
C6—C1—C2—C3 | 1.1 (7) | C3—C4—C7—N1 | −11.4 (6) |
Cl1—C1—C2—C3 | −178.0 (3) | C5—C4—C7—Se1 | −11.1 (6) |
C1—C2—C3—C4 | −0.2 (7) | C3—C4—C7—Se1 | 169.0 (3) |
C2—C3—C4—C5 | −1.1 (6) | C8—Se1—C7—N1 | 0.0 (3) |
C2—C3—C4—C7 | 178.7 (4) | C8—Se1—C7—C4 | 179.7 (3) |
C3—C4—C5—C6 | 1.7 (7) | C7—Se1—C8—C9 | 0.3 (3) |
C7—C4—C5—C6 | −178.2 (5) | Se1—C8—C9—N1 | −0.6 (5) |
C2—C1—C6—C5 | −0.6 (7) | Se1—C8—C9—C10 | −178.4 (3) |
Cl1—C1—C6—C5 | 178.5 (4) | C7—N1—C9—C8 | 0.6 (5) |
C4—C5—C6—C1 | −0.8 (7) | C7—N1—C9—C10 | 178.6 (4) |
C9—N1—C7—C4 | −180.0 (4) | C8—C9—C10—O1 | −117.4 (4) |
C9—N1—C7—Se1 | −0.3 (4) | N1—C9—C10—O1 | 64.8 (5) |
C5—C4—C7—N1 | 168.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.07 | 2.891 (5) | 174 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H8ClNOSe |
Mr | 272.58 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 14.8150 (15), 4.5707 (4), 14.9123 (14) |
β (°) | 96.642 (1) |
V (Å3) | 1003.01 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.97 |
Crystal size (mm) | 0.35 × 0.32 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.337, 0.587 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4466, 1742, 1318 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.104, 1.01 |
No. of reflections | 1742 |
No. of parameters | 128 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.45 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.07 | 2.891 (5) | 173.6 |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
We acknowledge the National Natural Foundation of China (21105042), the National Basic Research Program (2010CB234601) and the Natural Science Foundation of Shandong Province (ZR2011BM007, ZR2010BQ021) for financial support.
References
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It has well been confirmed that selenium-containing heterocyclic compounds are of considerable biochemical and pharmacological relevance. Thus, derivatives of selenazole have been extensively studied not only because of their interesting reactivities but also because of their pharmaceutical applications (Koketsu & Ishihara, 2003; Geisler et al., 2004). Interested in this field, the title compound, a derivative of selenazole, was prepared and its crystal structure presented (Fig. 1). In the title compound, C10H8NOClSe, the dihedral angle between the nearly planar benzene and selenazole rings is 11.4 (3)°. The dihedral angle between the selenazole ring and the hydroxymethyl group, defined by C9—C10–O1, is 63.8 (3)°. All the bond lengths and angles are normal and correspond to those observed in the related compounds (Shen et al., 2011; Shi & Zhao, 2007). In the crystal structure, pairs of molecules are disposed about an inversion center, generating dimers linked by intermolecular O—H···N hydrogen bonds (Fig. 2 and Table 1). The aromatic parts of the molecules are stacked along [010] (b = 4.5707 (4) Å) in a roof tile-like fashion enabling slipped π-π-stacking interactions. The face-to-face distance of the aromatic parts of the molecules (Se1, N1, C1 – C9) is 3.57 Å and their slippage 2.85 Å approximately parallel to the ring-to-ring bond C4—C7 (Fig. 2). This brings Cl1 in a position above/below the ring centroid of an adjacent benzene ring (Cl···centroid (C1 – C6) = 3.68 Å).