Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017485/at2267sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017485/at2267Isup2.hkl |
CCDC reference: 647579
The title compound was synthesized using the same procedure as in our previous paper (Köysal et al., 2007).
H atoms were located geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H, 0.97Å for CH2 and 0.96 Å for methyl H.
The structure of the title compound, (I) (Fig. 1), differs from that reported for 3-[(5-methyl-2-benzoxazolinone-3-yl)methyl] -4-allyl-1H-1,2,4-triazole-5(4H)-thione, (II) (Köysal et al., 2007).
The dihedral angle between the triazole ring and the benzoxazoline ring system is 88.20 (4)°, showing that these ring systems are almost perpendicular to each other. Both compounds (I) and (II) exhibit weak but slightly different intermolecular interactions. In (I), there is an N—H···O interaction, while in (II), the interactions are N—H···S, C—H···S and π–π.
The title compound is a similar isomorph of 3-[(5-methyl-2-benzoxazolinone-3-yl)methyl]-4-allyl-1H-1,2,4- triazole-5(4H)-thione (Köysal et al., 2007). The molecular geometry of the title compound is in agreement with values in our related structures (Köysal et al., 2003, 2007).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C17H14N4O2S | F(000) = 704 |
Mr = 338.38 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21935 reflections |
a = 12.2347 (6) Å | θ = 2.4–28.0° |
b = 12.8379 (7) Å | µ = 0.22 mm−1 |
c = 11.0797 (6) Å | T = 293 K |
β = 112.531 (4)° | Prism, colourless |
V = 1607.43 (15) Å3 | 0.54 × 0.39 × 0.24 mm |
Z = 4 |
Stoe IPDS II diffractometer | 3150 independent reflections |
Radiation source: fine-focus sealed tube | 2436 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −15→15 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.484, Tmax = 0.849 | l = −13→13 |
20943 measured reflections |
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) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.0405P] where P = (Fo2 + 2Fc2)/3 |
3150 reflections | (Δ/σ)max = 0.002 |
222 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C17H14N4O2S | V = 1607.43 (15) Å3 |
Mr = 338.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2347 (6) Å | µ = 0.22 mm−1 |
b = 12.8379 (7) Å | T = 293 K |
c = 11.0797 (6) Å | 0.54 × 0.39 × 0.24 mm |
β = 112.531 (4)° |
Stoe IPDS II diffractometer | 3150 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2436 reflections with I > 2σ(I) |
Tmin = 0.484, Tmax = 0.849 | Rint = 0.074 |
20943 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.21 e Å−3 |
3150 reflections | Δρmin = −0.27 e Å−3 |
222 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 | 0.92413 (16) | 0.44503 (12) | 0.32666 (15) | 0.0450 (4) | |
C2 | 1.02318 (16) | 0.39451 (13) | 0.40705 (17) | 0.0495 (4) | |
H2 | 1.0952 | 0.4001 | 0.3974 | 0.059* | |
C3 | 1.00960 (17) | 0.33420 (13) | 0.50425 (17) | 0.0512 (4) | |
H3 | 1.0744 | 0.2969 | 0.5601 | 0.061* | |
C4 | 0.90390 (16) | 0.32719 (13) | 0.52166 (17) | 0.0505 (4) | |
C5 | 0.80410 (16) | 0.38007 (13) | 0.43740 (16) | 0.0480 (4) | |
H5 | 0.7319 | 0.3761 | 0.4470 | 0.058* | |
C6 | 0.81727 (15) | 0.43839 (12) | 0.33947 (15) | 0.0434 (4) | |
C7 | 0.8973 (2) | 0.26370 (18) | 0.6325 (2) | 0.0726 (6) | |
H7A | 0.9207 | 0.1933 | 0.6255 | 0.109* | |
H7B | 0.8177 | 0.2643 | 0.6289 | 0.109* | |
H7C | 0.9494 | 0.2929 | 0.7141 | 0.109* | |
C8 | 0.79970 (19) | 0.54601 (15) | 0.17374 (18) | 0.0587 (5) | |
C9 | 0.61703 (16) | 0.52145 (14) | 0.21542 (17) | 0.0535 (4) | |
H9A | 0.5796 | 0.4582 | 0.2284 | 0.064* | |
H9B | 0.5767 | 0.5430 | 0.1252 | 0.064* | |
C10 | 0.60490 (15) | 0.60493 (12) | 0.30378 (16) | 0.0465 (4) | |
C11 | 0.52524 (16) | 0.71128 (12) | 0.40576 (17) | 0.0483 (4) | |
C12 | 0.39529 (16) | 0.56646 (13) | 0.27743 (16) | 0.0471 (4) | |
C13 | 0.3941 (2) | 0.46557 (14) | 0.31950 (19) | 0.0606 (5) | |
H13 | 0.4625 | 0.4353 | 0.3792 | 0.073* | |
C14 | 0.2889 (2) | 0.41019 (17) | 0.2710 (2) | 0.0742 (6) | |
H14 | 0.2868 | 0.3416 | 0.2969 | 0.089* | |
C15 | 0.1879 (2) | 0.4560 (2) | 0.1850 (2) | 0.0777 (7) | |
H15 | 0.1174 | 0.4187 | 0.1534 | 0.093* | |
C16 | 0.1908 (2) | 0.5569 (2) | 0.1453 (2) | 0.0775 (6) | |
H16 | 0.1219 | 0.5879 | 0.0875 | 0.093* | |
C17 | 0.29451 (18) | 0.61215 (16) | 0.19043 (19) | 0.0612 (5) | |
H17 | 0.2966 | 0.6801 | 0.1623 | 0.073* | |
N1 | 0.73919 (13) | 0.50064 (11) | 0.24030 (13) | 0.0497 (3) | |
N2 | 0.50386 (12) | 0.62461 (10) | 0.32577 (13) | 0.0450 (3) | |
N3 | 0.63611 (14) | 0.73594 (12) | 0.42496 (16) | 0.0541 (4) | |
N4 | 0.68742 (14) | 0.67115 (12) | 0.36309 (15) | 0.0540 (4) | |
O1 | 0.91324 (12) | 0.51094 (10) | 0.22290 (12) | 0.0577 (3) | |
O2 | 0.76463 (17) | 0.60708 (14) | 0.08433 (16) | 0.0892 (5) | |
S1 | 0.43585 (5) | 0.76920 (4) | 0.46729 (5) | 0.06125 (17) | |
H3A | 0.678 (2) | 0.7849 (18) | 0.475 (2) | 0.064 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0550 (10) | 0.0402 (8) | 0.0446 (8) | 0.0023 (7) | 0.0246 (7) | −0.0024 (6) |
C2 | 0.0462 (10) | 0.0515 (9) | 0.0545 (9) | 0.0042 (7) | 0.0234 (8) | −0.0051 (7) |
C3 | 0.0482 (10) | 0.0496 (9) | 0.0508 (9) | 0.0072 (7) | 0.0136 (7) | 0.0001 (7) |
C4 | 0.0541 (11) | 0.0461 (9) | 0.0506 (9) | 0.0016 (7) | 0.0191 (8) | 0.0031 (7) |
C5 | 0.0468 (10) | 0.0442 (8) | 0.0557 (9) | −0.0012 (7) | 0.0226 (7) | 0.0012 (7) |
C6 | 0.0473 (10) | 0.0369 (7) | 0.0441 (8) | 0.0052 (6) | 0.0156 (7) | −0.0035 (6) |
C7 | 0.0757 (15) | 0.0754 (13) | 0.0699 (13) | 0.0115 (11) | 0.0315 (11) | 0.0253 (11) |
C8 | 0.0747 (14) | 0.0557 (10) | 0.0527 (10) | 0.0202 (9) | 0.0321 (9) | 0.0085 (8) |
C9 | 0.0503 (11) | 0.0523 (10) | 0.0517 (9) | 0.0110 (8) | 0.0129 (8) | −0.0056 (8) |
C10 | 0.0450 (10) | 0.0432 (8) | 0.0491 (9) | 0.0077 (7) | 0.0156 (7) | 0.0016 (7) |
C11 | 0.0529 (11) | 0.0389 (8) | 0.0539 (9) | 0.0010 (7) | 0.0213 (8) | −0.0007 (7) |
C12 | 0.0510 (11) | 0.0435 (8) | 0.0505 (9) | −0.0031 (7) | 0.0234 (8) | −0.0043 (7) |
C13 | 0.0740 (14) | 0.0496 (10) | 0.0611 (11) | −0.0045 (9) | 0.0291 (10) | 0.0014 (8) |
C14 | 0.1024 (19) | 0.0557 (11) | 0.0797 (14) | −0.0269 (12) | 0.0518 (14) | −0.0117 (10) |
C15 | 0.0731 (16) | 0.0910 (17) | 0.0760 (14) | −0.0338 (13) | 0.0364 (12) | −0.0251 (12) |
C16 | 0.0526 (13) | 0.0966 (17) | 0.0763 (14) | −0.0113 (11) | 0.0167 (10) | −0.0112 (12) |
C17 | 0.0531 (12) | 0.0587 (11) | 0.0678 (12) | −0.0005 (9) | 0.0187 (9) | 0.0017 (9) |
N1 | 0.0524 (9) | 0.0478 (7) | 0.0493 (7) | 0.0130 (6) | 0.0201 (6) | 0.0032 (6) |
N2 | 0.0444 (8) | 0.0393 (7) | 0.0506 (7) | 0.0017 (6) | 0.0174 (6) | −0.0012 (5) |
N3 | 0.0494 (9) | 0.0474 (8) | 0.0661 (9) | −0.0049 (7) | 0.0228 (7) | −0.0132 (7) |
N4 | 0.0461 (9) | 0.0528 (8) | 0.0628 (9) | 0.0018 (6) | 0.0204 (7) | −0.0095 (7) |
O1 | 0.0681 (9) | 0.0596 (7) | 0.0556 (7) | 0.0148 (6) | 0.0352 (6) | 0.0106 (6) |
O2 | 0.1090 (14) | 0.0961 (11) | 0.0760 (10) | 0.0471 (10) | 0.0503 (9) | 0.0423 (9) |
S1 | 0.0609 (3) | 0.0541 (3) | 0.0784 (3) | −0.0008 (2) | 0.0374 (3) | −0.0130 (2) |
C1—C2 | 1.362 (2) | C9—H9B | 0.9700 |
C1—C6 | 1.371 (2) | C10—N4 | 1.290 (2) |
C1—O1 | 1.3922 (19) | C10—N2 | 1.372 (2) |
C2—C3 | 1.387 (3) | C11—N3 | 1.328 (2) |
C2—H2 | 0.9300 | C11—N2 | 1.384 (2) |
C3—C4 | 1.382 (3) | C11—S1 | 1.6689 (18) |
C3—H3 | 0.9300 | C12—C17 | 1.372 (3) |
C4—C5 | 1.396 (2) | C12—C13 | 1.379 (2) |
C4—C7 | 1.502 (3) | C12—N2 | 1.436 (2) |
C5—C6 | 1.378 (2) | C13—C14 | 1.386 (3) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—N1 | 1.398 (2) | C14—C15 | 1.371 (4) |
C7—H7A | 0.9600 | C14—H14 | 0.9300 |
C7—H7B | 0.9600 | C15—C16 | 1.371 (4) |
C7—H7C | 0.9600 | C15—H15 | 0.9300 |
C8—O2 | 1.206 (2) | C16—C17 | 1.371 (3) |
C8—O1 | 1.360 (2) | C16—H16 | 0.9300 |
C8—N1 | 1.360 (2) | C17—H17 | 0.9300 |
C9—N1 | 1.437 (2) | N3—N4 | 1.373 (2) |
C9—C10 | 1.497 (2) | N3—H3A | 0.86 (2) |
C9—H9A | 0.9700 | ||
C2—C1—C6 | 123.21 (15) | N4—C10—C9 | 123.39 (17) |
C2—C1—O1 | 127.52 (15) | N2—C10—C9 | 124.74 (15) |
C6—C1—O1 | 109.27 (14) | N3—C11—N2 | 103.01 (14) |
C1—C2—C3 | 115.61 (16) | N3—C11—S1 | 128.11 (14) |
C1—C2—H2 | 122.2 | N2—C11—S1 | 128.85 (14) |
C3—C2—H2 | 122.2 | C17—C12—C13 | 121.08 (18) |
C4—C3—C2 | 122.81 (16) | C17—C12—N2 | 119.57 (16) |
C4—C3—H3 | 118.6 | C13—C12—N2 | 119.35 (17) |
C2—C3—H3 | 118.6 | C12—C13—C14 | 118.6 (2) |
C3—C4—C5 | 120.03 (16) | C12—C13—H13 | 120.7 |
C3—C4—C7 | 119.74 (17) | C14—C13—H13 | 120.7 |
C5—C4—C7 | 120.23 (17) | C15—C14—C13 | 120.3 (2) |
C6—C5—C4 | 117.04 (16) | C15—C14—H14 | 119.8 |
C6—C5—H5 | 121.5 | C13—C14—H14 | 119.8 |
C4—C5—H5 | 121.5 | C14—C15—C16 | 120.1 (2) |
C1—C6—C5 | 121.29 (15) | C14—C15—H15 | 120.0 |
C1—C6—N1 | 105.95 (14) | C16—C15—H15 | 120.0 |
C5—C6—N1 | 132.75 (16) | C17—C16—C15 | 120.4 (2) |
C4—C7—H7A | 109.5 | C17—C16—H16 | 119.8 |
C4—C7—H7B | 109.5 | C15—C16—H16 | 119.8 |
H7A—C7—H7B | 109.5 | C16—C17—C12 | 119.5 (2) |
C4—C7—H7C | 109.5 | C16—C17—H17 | 120.3 |
H7A—C7—H7C | 109.5 | C12—C17—H17 | 120.3 |
H7B—C7—H7C | 109.5 | C8—N1—C6 | 108.72 (15) |
O2—C8—O1 | 122.11 (19) | C8—N1—C9 | 123.96 (15) |
O2—C8—N1 | 128.9 (2) | C6—N1—C9 | 127.18 (15) |
O1—C8—N1 | 109.02 (14) | C10—N2—C11 | 107.44 (14) |
N1—C9—C10 | 111.35 (15) | C10—N2—C12 | 127.27 (13) |
N1—C9—H9A | 109.4 | C11—N2—C12 | 125.28 (14) |
C10—C9—H9A | 109.4 | C11—N3—N4 | 114.19 (15) |
N1—C9—H9B | 109.4 | C11—N3—H3A | 126.6 (15) |
C10—C9—H9B | 109.4 | N4—N3—H3A | 119.1 (15) |
H9A—C9—H9B | 108.0 | C10—N4—N3 | 103.60 (15) |
N4—C10—N2 | 111.76 (14) | C8—O1—C1 | 106.97 (13) |
C6—C1—C2—C3 | 0.4 (2) | C1—C6—N1—C8 | −2.22 (18) |
O1—C1—C2—C3 | 179.27 (15) | C5—C6—N1—C8 | 176.59 (18) |
C1—C2—C3—C4 | −1.6 (3) | C1—C6—N1—C9 | −177.99 (15) |
C2—C3—C4—C5 | 1.7 (3) | C5—C6—N1—C9 | 0.8 (3) |
C2—C3—C4—C7 | −177.52 (18) | C10—C9—N1—C8 | −94.1 (2) |
C3—C4—C5—C6 | −0.4 (2) | C10—C9—N1—C6 | 81.0 (2) |
C7—C4—C5—C6 | 178.76 (17) | N4—C10—N2—C11 | 0.23 (19) |
C2—C1—C6—C5 | 0.8 (2) | C9—C10—N2—C11 | −176.15 (15) |
O1—C1—C6—C5 | −178.26 (14) | N4—C10—N2—C12 | −178.99 (15) |
C2—C1—C6—N1 | 179.81 (15) | C9—C10—N2—C12 | 4.6 (3) |
O1—C1—C6—N1 | 0.72 (17) | N3—C11—N2—C10 | −0.08 (17) |
C4—C5—C6—C1 | −0.8 (2) | S1—C11—N2—C10 | −178.44 (14) |
C4—C5—C6—N1 | −179.45 (16) | N3—C11—N2—C12 | 179.15 (15) |
N1—C9—C10—N4 | 20.4 (2) | S1—C11—N2—C12 | 0.8 (2) |
N1—C9—C10—N2 | −163.63 (15) | C17—C12—N2—C10 | −114.18 (19) |
C17—C12—C13—C14 | 0.7 (3) | C13—C12—N2—C10 | 65.9 (2) |
N2—C12—C13—C14 | −179.39 (17) | C17—C12—N2—C11 | 66.7 (2) |
C12—C13—C14—C15 | −1.3 (3) | C13—C12—N2—C11 | −113.16 (19) |
C13—C14—C15—C16 | 0.7 (3) | N2—C11—N3—N4 | −0.1 (2) |
C14—C15—C16—C17 | 0.5 (4) | S1—C11—N3—N4 | 178.30 (13) |
C15—C16—C17—C12 | −1.1 (3) | N2—C10—N4—N3 | −0.26 (19) |
C13—C12—C17—C16 | 0.5 (3) | C9—C10—N4—N3 | 176.17 (15) |
N2—C12—C17—C16 | −179.42 (18) | C11—N3—N4—C10 | 0.2 (2) |
O2—C8—N1—C6 | −177.7 (2) | O2—C8—O1—C1 | 178.11 (19) |
O1—C8—N1—C6 | 2.9 (2) | N1—C8—O1—C1 | −2.43 (19) |
O2—C8—N1—C9 | −1.7 (3) | C2—C1—O1—C8 | −178.01 (17) |
O1—C8—N1—C9 | 178.87 (14) | C6—C1—O1—C8 | 1.03 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.86 (2) | 1.88 (2) | 2.743 (2) | 178 (2) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14N4O2S |
Mr | 338.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.2347 (6), 12.8379 (7), 11.0797 (6) |
β (°) | 112.531 (4) |
V (Å3) | 1607.43 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.54 × 0.39 × 0.24 |
Data collection | |
Diffractometer | Stoe IPDS II |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.484, 0.849 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20943, 3150, 2436 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.109, 1.03 |
No. of reflections | 3150 |
No. of parameters | 222 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.27 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C8—O2 | 1.206 (2) | N3—N4 | 1.373 (2) |
C10—N4 | 1.290 (2) | ||
N1—C9—C10 | 111.35 (15) | ||
N1—C9—C10—N2 | −163.63 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.86 (2) | 1.88 (2) | 2.743 (2) | 178 (2) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
The structure of the title compound, (I) (Fig. 1), differs from that reported for 3-[(5-methyl-2-benzoxazolinone-3-yl)methyl] -4-allyl-1H-1,2,4-triazole-5(4H)-thione, (II) (Köysal et al., 2007).
The dihedral angle between the triazole ring and the benzoxazoline ring system is 88.20 (4)°, showing that these ring systems are almost perpendicular to each other. Both compounds (I) and (II) exhibit weak but slightly different intermolecular interactions. In (I), there is an N—H···O interaction, while in (II), the interactions are N—H···S, C—H···S and π–π.