organic compounds
1-(1,3-Benzothiazol-2-yl)-3-phenyl-2-pyrazoline
aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China
*Correspondence e-mail: hrb1018@163.com
In the title compound, C16H13N3S, the pyrazoline ring forms dihedral angles of 6.89 (14) and 4.96 (11)° with the benzene ring and the benzothiazole group, respectively. In the crystal, weak C—H⋯N interactions link the molecules into chains extending along the b-axis direction.
Related literature
For background to the title compound, see: Sano et al. (1995); Xian et al. (2008). For details of the synthesis, see: Xian et al. (2008).
Experimental
Crystal data
|
Refinement
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (MSC & Rigaku, 2002); 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: SHELXL97.
Supporting information
10.1107/S1600536812013219/gk2466sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812013219/gk2466Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812013219/gk2466Isup3.cml
The title compound was prepared according to the literature (Xian et al., 2008). Single crystals suitable for X-ray diffraction were prepared by slow evaporation method from a solution in dichloromethane/petroleum (60–90 °C) at room temperature.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 and 0.97 Å) and were included in the
in the riding model approximation with Uiso(H) = 1.2 Ueq(C).Pyrazoline derivatives have been investigated in many repects due to their blue light emission with high
accessibility. They are used as carrier transporting as well as emitting materials (Sano et al., 1995). Recently, Xian reported the synthesis and optical properties of novel pyrazoline derivatives as blue light fluorescence compounds (Xian et al., 2008). In this paper, we describe the of the title compound with blue light fluorescence.The molecular structure of title compound, C16H13N3S, is shown in Fig. 1, all bond lengths and angles are in the normal ranges. The pyrazoline ring and benzothiazole ring are nearly coplanar and make dihedral angle of 4.96 (11)°. The molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1), generating chains along the b direction.
For background to the title compound, see: Sano et al. (1995); Xian et al. (2008). For details of the synthesis, see: Xian et al. (2008).
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (MSC & Rigaku, 2002); 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: SHELXL97 (Sheldrick, 2008).Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probalility level. |
C16H13N3S | F(000) = 584 |
Mr = 279.35 | Dx = 1.340 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8759 reflections |
a = 16.946 (8) Å | θ = 3.6–27.6° |
b = 5.449 (3) Å | µ = 0.23 mm−1 |
c = 17.306 (11) Å | T = 288 K |
β = 119.96 (2)° | Block, colorless |
V = 1384.4 (14) Å3 | 0.54 × 0.30 × 0.28 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3141 independent reflections |
Radiation source: fine-focus sealed tube | 2227 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −21→21 |
Tmin = 0.887, Tmax = 0.938 | k = −7→6 |
11972 measured reflections | l = −22→22 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0607P)2 + 0.0076P] where P = (Fo2 + 2Fc2)/3 |
3141 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C16H13N3S | V = 1384.4 (14) Å3 |
Mr = 279.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.946 (8) Å | µ = 0.23 mm−1 |
b = 5.449 (3) Å | T = 288 K |
c = 17.306 (11) Å | 0.54 × 0.30 × 0.28 mm |
β = 119.96 (2)° |
Rigaku R-AXIS RAPID diffractometer | 3141 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2227 reflections with I > 2σ(I) |
Tmin = 0.887, Tmax = 0.938 | Rint = 0.028 |
11972 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.20 e Å−3 |
3141 reflections | Δρmin = −0.20 e Å−3 |
181 parameters |
Experimental. (See detailed section in the paper) |
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 | ||
S1 | 0.50225 (3) | −0.17993 (8) | 0.32651 (3) | 0.05497 (16) | |
N1 | 0.43537 (9) | 0.1902 (2) | 0.37317 (10) | 0.0552 (4) | |
N2 | 0.59086 (9) | 0.1280 (3) | 0.46547 (10) | 0.0569 (4) | |
N3 | 0.66870 (9) | 0.0055 (2) | 0.48121 (9) | 0.0541 (3) | |
C1 | 0.38592 (10) | −0.1199 (3) | 0.26333 (11) | 0.0502 (4) | |
C2 | 0.32007 (12) | −0.2465 (4) | 0.18951 (13) | 0.0617 (5) | |
H2 | 0.3354 | −0.3833 | 0.1677 | 0.074* | |
C3 | 0.23125 (12) | −0.1641 (4) | 0.14930 (13) | 0.0678 (5) | |
H3 | 0.1862 | −0.2452 | 0.0994 | 0.081* | |
C4 | 0.20868 (12) | 0.0380 (4) | 0.18261 (13) | 0.0690 (5) | |
H4 | 0.1485 | 0.0913 | 0.1544 | 0.083* | |
C5 | 0.27335 (12) | 0.1621 (3) | 0.25656 (13) | 0.0629 (5) | |
H5 | 0.2570 | 0.2966 | 0.2786 | 0.075* | |
C6 | 0.36345 (10) | 0.0836 (3) | 0.29788 (11) | 0.0509 (4) | |
C7 | 0.50936 (10) | 0.0702 (3) | 0.39398 (11) | 0.0499 (4) | |
C8 | 0.60831 (11) | 0.3438 (3) | 0.52172 (12) | 0.0554 (4) | |
H8A | 0.5770 | 0.3329 | 0.5557 | 0.066* | |
H8B | 0.5901 | 0.4934 | 0.4867 | 0.066* | |
C9 | 0.71109 (11) | 0.3312 (3) | 0.58214 (12) | 0.0568 (4) | |
H9A | 0.7402 | 0.4805 | 0.5784 | 0.068* | |
H9B | 0.7274 | 0.3038 | 0.6437 | 0.068* | |
C10 | 0.73713 (11) | 0.1147 (3) | 0.54526 (11) | 0.0493 (4) | |
C11 | 0.83120 (11) | 0.0387 (3) | 0.57541 (12) | 0.0546 (4) | |
C12 | 0.85070 (13) | −0.1548 (4) | 0.53559 (14) | 0.0704 (5) | |
H12 | 0.8037 | −0.2453 | 0.4906 | 0.085* | |
C13 | 0.94034 (15) | −0.2128 (5) | 0.56296 (17) | 0.0892 (7) | |
H13 | 0.9533 | −0.3426 | 0.5362 | 0.107* | |
C14 | 1.01079 (15) | −0.0798 (5) | 0.62958 (18) | 0.0935 (7) | |
H14 | 1.0709 | −0.1183 | 0.6471 | 0.112* | |
C15 | 0.99182 (13) | 0.1075 (5) | 0.66937 (17) | 0.0882 (7) | |
H15 | 1.0392 | 0.1961 | 0.7147 | 0.106* | |
C16 | 0.90289 (12) | 0.1677 (4) | 0.64329 (14) | 0.0725 (5) | |
H16 | 0.8909 | 0.2958 | 0.6714 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0594 (3) | 0.0536 (3) | 0.0590 (3) | 0.00083 (18) | 0.0349 (2) | −0.00678 (19) |
N1 | 0.0564 (8) | 0.0489 (8) | 0.0602 (9) | −0.0009 (6) | 0.0290 (7) | −0.0076 (6) |
N2 | 0.0519 (7) | 0.0566 (8) | 0.0600 (9) | 0.0041 (6) | 0.0262 (7) | −0.0112 (7) |
N3 | 0.0600 (8) | 0.0525 (8) | 0.0543 (8) | 0.0057 (6) | 0.0318 (7) | −0.0010 (6) |
C1 | 0.0578 (9) | 0.0483 (9) | 0.0526 (9) | −0.0047 (7) | 0.0336 (8) | −0.0014 (7) |
C2 | 0.0682 (11) | 0.0625 (10) | 0.0650 (12) | −0.0099 (8) | 0.0413 (9) | −0.0154 (9) |
C3 | 0.0627 (10) | 0.0779 (13) | 0.0625 (12) | −0.0164 (9) | 0.0311 (9) | −0.0172 (9) |
C4 | 0.0552 (10) | 0.0773 (13) | 0.0703 (13) | −0.0026 (9) | 0.0281 (9) | −0.0058 (10) |
C5 | 0.0601 (9) | 0.0554 (11) | 0.0721 (12) | 0.0015 (8) | 0.0322 (9) | −0.0074 (9) |
C6 | 0.0569 (9) | 0.0448 (9) | 0.0544 (10) | −0.0052 (7) | 0.0304 (8) | −0.0018 (7) |
C7 | 0.0570 (9) | 0.0450 (9) | 0.0533 (10) | −0.0026 (7) | 0.0317 (8) | −0.0020 (7) |
C8 | 0.0613 (9) | 0.0485 (9) | 0.0548 (10) | 0.0041 (7) | 0.0279 (8) | −0.0052 (7) |
C9 | 0.0593 (9) | 0.0516 (10) | 0.0588 (11) | 0.0004 (7) | 0.0291 (8) | −0.0049 (8) |
C10 | 0.0564 (9) | 0.0482 (9) | 0.0478 (9) | 0.0045 (7) | 0.0294 (7) | 0.0060 (7) |
C11 | 0.0592 (9) | 0.0552 (10) | 0.0550 (10) | 0.0082 (8) | 0.0327 (8) | 0.0117 (8) |
C12 | 0.0716 (11) | 0.0737 (13) | 0.0710 (13) | 0.0159 (9) | 0.0393 (10) | 0.0026 (10) |
C13 | 0.0864 (15) | 0.0968 (17) | 0.0963 (18) | 0.0324 (13) | 0.0546 (14) | 0.0062 (14) |
C14 | 0.0644 (12) | 0.118 (2) | 0.1009 (19) | 0.0243 (13) | 0.0430 (13) | 0.0210 (16) |
C15 | 0.0573 (11) | 0.0989 (16) | 0.0930 (17) | 0.0079 (11) | 0.0259 (11) | 0.0044 (14) |
C16 | 0.0586 (10) | 0.0765 (13) | 0.0736 (14) | 0.0073 (9) | 0.0264 (10) | 0.0004 (10) |
S1—C1 | 1.7424 (18) | C8—C9 | 1.521 (2) |
S1—C7 | 1.7591 (18) | C8—H8A | 0.9700 |
N1—C7 | 1.296 (2) | C8—H8B | 0.9700 |
N1—C6 | 1.391 (2) | C9—C10 | 1.508 (2) |
N2—C7 | 1.353 (2) | C9—H9A | 0.9700 |
N2—N3 | 1.3788 (18) | C9—H9B | 0.9700 |
N2—C8 | 1.459 (2) | C10—C11 | 1.468 (2) |
N3—C10 | 1.282 (2) | C11—C12 | 1.387 (3) |
C1—C2 | 1.389 (2) | C11—C16 | 1.387 (3) |
C1—C6 | 1.400 (2) | C12—C13 | 1.383 (3) |
C2—C3 | 1.380 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.380 (3) |
C3—C4 | 1.382 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.356 (4) |
C4—C5 | 1.377 (2) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.379 (3) |
C5—C6 | 1.391 (2) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C1—S1—C7 | 87.26 (8) | N2—C8—H8B | 111.4 |
C7—N1—C6 | 108.86 (14) | C9—C8—H8B | 111.4 |
C7—N2—N3 | 120.46 (14) | H8A—C8—H8B | 109.3 |
C7—N2—C8 | 124.87 (14) | C10—C9—C8 | 102.76 (13) |
N3—N2—C8 | 113.78 (13) | C10—C9—H9A | 111.2 |
C10—N3—N2 | 108.00 (14) | C8—C9—H9A | 111.2 |
C2—C1—C6 | 121.40 (15) | C10—C9—H9B | 111.2 |
C2—C1—S1 | 128.44 (14) | C8—C9—H9B | 111.2 |
C6—C1—S1 | 110.15 (12) | H9A—C9—H9B | 109.1 |
C3—C2—C1 | 118.38 (17) | N3—C10—C11 | 121.95 (15) |
C3—C2—H2 | 120.8 | N3—C10—C9 | 113.54 (13) |
C1—C2—H2 | 120.8 | C11—C10—C9 | 124.44 (15) |
C2—C3—C4 | 120.52 (17) | C12—C11—C16 | 118.72 (16) |
C2—C3—H3 | 119.7 | C12—C11—C10 | 121.59 (17) |
C4—C3—H3 | 119.7 | C16—C11—C10 | 119.65 (16) |
C5—C4—C3 | 121.41 (17) | C13—C12—C11 | 119.8 (2) |
C5—C4—H4 | 119.3 | C13—C12—H12 | 120.1 |
C3—C4—H4 | 119.3 | C11—C12—H12 | 120.1 |
C4—C5—C6 | 119.12 (16) | C14—C13—C12 | 120.7 (2) |
C4—C5—H5 | 120.4 | C14—C13—H13 | 119.7 |
C6—C5—H5 | 120.4 | C12—C13—H13 | 119.7 |
N1—C6—C5 | 125.20 (15) | C15—C14—C13 | 119.6 (2) |
N1—C6—C1 | 115.65 (14) | C15—C14—H14 | 120.2 |
C5—C6—C1 | 119.14 (15) | C13—C14—H14 | 120.2 |
N1—C7—N2 | 122.74 (15) | C14—C15—C16 | 120.7 (2) |
N1—C7—S1 | 118.07 (12) | C14—C15—H15 | 119.7 |
N2—C7—S1 | 119.18 (12) | C16—C15—H15 | 119.7 |
N2—C8—C9 | 101.73 (12) | C15—C16—C11 | 120.6 (2) |
N2—C8—H8A | 111.4 | C15—C16—H16 | 119.7 |
C9—C8—H8A | 111.4 | C11—C16—H16 | 119.7 |
C7—N2—N3—C10 | 171.82 (15) | C8—N2—C7—S1 | 173.69 (13) |
C8—N2—N3—C10 | 2.14 (19) | C1—S1—C7—N1 | −0.77 (13) |
C7—S1—C1—C2 | −178.47 (17) | C1—S1—C7—N2 | 178.58 (14) |
C7—S1—C1—C6 | 0.79 (12) | C7—N2—C8—C9 | −173.15 (16) |
C6—C1—C2—C3 | 1.2 (3) | N3—N2—C8—C9 | −4.01 (18) |
S1—C1—C2—C3 | −179.59 (14) | N2—C8—C9—C10 | 3.99 (16) |
C1—C2—C3—C4 | −0.7 (3) | N2—N3—C10—C11 | −176.45 (14) |
C2—C3—C4—C5 | −0.3 (3) | N2—N3—C10—C9 | 0.87 (19) |
C3—C4—C5—C6 | 0.7 (3) | C8—C9—C10—N3 | −3.27 (19) |
C7—N1—C6—C5 | 179.52 (15) | C8—C9—C10—C11 | 173.97 (15) |
C7—N1—C6—C1 | 0.2 (2) | N3—C10—C11—C12 | 0.4 (3) |
C4—C5—C6—N1 | −179.49 (17) | C9—C10—C11—C12 | −176.66 (16) |
C4—C5—C6—C1 | −0.2 (3) | N3—C10—C11—C16 | 178.12 (17) |
C2—C1—C6—N1 | 178.56 (15) | C9—C10—C11—C16 | 1.1 (2) |
S1—C1—C6—N1 | −0.76 (18) | C16—C11—C12—C13 | −1.0 (3) |
C2—C1—C6—C5 | −0.8 (3) | C10—C11—C12—C13 | 176.74 (18) |
S1—C1—C6—C5 | 179.88 (13) | C11—C12—C13—C14 | 0.0 (3) |
C6—N1—C7—N2 | −178.85 (15) | C12—C13—C14—C15 | 0.9 (4) |
C6—N1—C7—S1 | 0.47 (18) | C13—C14—C15—C16 | −0.6 (4) |
N3—N2—C7—N1 | −175.46 (14) | C14—C15—C16—C11 | −0.4 (4) |
C8—N2—C7—N1 | −7.0 (3) | C12—C11—C16—C15 | 1.3 (3) |
N3—N2—C7—S1 | 5.2 (2) | C10—C11—C16—C15 | −176.54 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3i | 0.93 | 2.61 | 3.340 (3) | 135 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H13N3S |
Mr | 279.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 288 |
a, b, c (Å) | 16.946 (8), 5.449 (3), 17.306 (11) |
β (°) | 119.96 (2) |
V (Å3) | 1384.4 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.54 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.887, 0.938 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11972, 3141, 2227 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.116, 1.14 |
No. of reflections | 3141 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (MSC & Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3i | 0.93 | 2.61 | 3.340 (3) | 135 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of Jilin Province (grant No. 20101548).
References
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
MSC & Rigaku (2002). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sano, T., Fuji, T., Nishio, Y., Hamada, Y., Shibata, K. & Kuroki, K. (1995). Jpn J. Appl. Phys. 34, 3124–3127. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xian, Y. F., Li, D. F. & Wang, Y. M. (2008). Spectrosc. Spect. Anal. 28, 1617–1620. CAS Google Scholar
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Pyrazoline derivatives have been investigated in many repects due to their blue light emission with high quantum yield, accessibility. They are used as carrier transporting as well as emitting materials (Sano et al., 1995). Recently, Xian reported the synthesis and optical properties of novel pyrazoline derivatives as blue light fluorescence compounds (Xian et al., 2008). In this paper, we describe the crystal structure of the title compound with blue light fluorescence.
The molecular structure of title compound, C16H13N3S, is shown in Fig. 1, all bond lengths and angles are in the normal ranges. The pyrazoline ring and benzothiazole ring are nearly coplanar and make dihedral angle of 4.96 (11)°. The molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1), generating chains along the b direction.