5-Phenyl-1,2,4-triazolo­[3,4-b]­benzo­thia­zole

In the title compound, C₁₄H₉N₃S, the triazole and benzo­thia­zole moieties are coplanar. The dihedral angle between the fused triazole–benzo­thia­zole fragment and the phenyl ring is 39.20 (5)°. The structure is stabilized by C—H...N intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.128
• Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.796
          Tmax scaled      0.794 Tmin scaled      0.735

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995).

5-Phenyl-1,2,4-triazolo[3,4-b]benzothiazole

Crystal data

C14H9N3S	F(000) = 520
Mr = 251.30	Dx = 1.425 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 8.702 (1) Å	Cell parameters from 25 reflections
b = 15.000 (2) Å	θ = 14–30°
c = 9.799 (1) Å	µ = 2.31 mm^−1
β = 113.70 (1)°	T = 293 K
V = 1171.2 (3) Å^3	Needle, yellow
Z = 4	0.35 × 0.13 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1936 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 69.9°, θmin = 5.6°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.924, Tmax = 0.998	l = −11→10
2277 measured reflections	3 standard reflections every 120min min
2128 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0798P)^2 + 0.27P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2128 reflections	Δρmax = 0.30 e Å^−3
164 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0126 (12)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.09869 (7)	0.20267 (3)	0.06743 (6)	0.0526 (2)
N1	0.18860 (18)	0.05486 (10)	0.21887 (16)	0.0403 (4)
N2	0.0898 (2)	0.15011 (11)	0.33779 (19)	0.0507 (4)
N3	0.1418 (2)	0.07211 (11)	0.42170 (18)	0.0480 (4)
C1	0.1727 (2)	0.11284 (13)	−0.0048 (2)	0.0456 (4)
C2	0.1848 (3)	0.11050 (15)	−0.1415 (2)	0.0563 (5)
H2	0.1585	0.1605	−0.2027	0.068*
C3	0.2365 (3)	0.03250 (17)	−0.1855 (2)	0.0607 (6)
H3	0.2476	0.0304	−0.2760	0.073*
C4	0.2718 (3)	−0.04229 (16)	−0.0960 (2)	0.0576 (5)
H4	0.3045	−0.0944	−0.1283	0.069*
C5	0.2598 (3)	−0.04160 (13)	0.0410 (2)	0.0483 (5)
H5	0.2823	−0.0925	0.0999	0.058*
C6	0.2132 (2)	0.03717 (12)	0.08716 (19)	0.0411 (4)
C7	0.1218 (2)	0.13753 (12)	0.2204 (2)	0.0450 (4)
C8	0.2003 (2)	0.01621 (12)	0.3508 (2)	0.0410 (4)
C9	0.2769 (2)	−0.06983 (12)	0.4138 (2)	0.0421 (4)
C10	0.2138 (3)	−0.11635 (14)	0.5030 (2)	0.0501 (5)
H10	0.1174	−0.0965	0.5125	0.060*
C11	0.2953 (3)	−0.19259 (15)	0.5775 (3)	0.0603 (6)
H11	0.2554	−0.2226	0.6397	0.072*
C13	0.4961 (3)	−0.17932 (15)	0.4692 (3)	0.0589 (5)
H13	0.5885	−0.2016	0.4554	0.071*
C12	0.4346 (3)	−0.22384 (16)	0.5599 (3)	0.0644 (6)
H12	0.4878	−0.2753	0.6094	0.077*
C14	0.4196 (2)	−0.10105 (14)	0.3986 (2)	0.0491 (5)
H14	0.4638	−0.0695	0.3410	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0677 (4)	0.0424 (3)	0.0513 (3)	0.0047 (2)	0.0278 (3)	0.00514 (19)
N1	0.0478 (8)	0.0391 (8)	0.0390 (8)	−0.0010 (6)	0.0227 (6)	−0.0027 (6)
N2	0.0597 (10)	0.0482 (9)	0.0509 (9)	0.0053 (7)	0.0292 (8)	−0.0022 (7)
N3	0.0575 (9)	0.0478 (9)	0.0464 (9)	−0.0002 (7)	0.0287 (8)	−0.0019 (7)
C1	0.0524 (10)	0.0443 (10)	0.0420 (10)	−0.0051 (8)	0.0211 (8)	−0.0024 (8)
C2	0.0716 (13)	0.0570 (12)	0.0439 (11)	−0.0067 (10)	0.0269 (10)	0.0036 (9)
C3	0.0737 (14)	0.0738 (15)	0.0408 (10)	−0.0095 (11)	0.0297 (10)	−0.0075 (10)
C4	0.0692 (13)	0.0601 (13)	0.0487 (11)	−0.0016 (10)	0.0290 (10)	−0.0132 (9)
C5	0.0580 (11)	0.0460 (10)	0.0445 (10)	−0.0005 (8)	0.0243 (9)	−0.0048 (8)
C6	0.0458 (9)	0.0433 (9)	0.0374 (9)	−0.0055 (7)	0.0202 (7)	−0.0026 (7)
C7	0.0517 (10)	0.0393 (10)	0.0477 (10)	0.0015 (7)	0.0239 (8)	−0.0016 (8)
C8	0.0463 (9)	0.0433 (10)	0.0385 (9)	−0.0046 (7)	0.0224 (7)	−0.0016 (7)
C9	0.0454 (9)	0.0425 (10)	0.0386 (9)	−0.0055 (7)	0.0171 (7)	−0.0037 (7)
C10	0.0541 (11)	0.0499 (11)	0.0493 (11)	−0.0047 (8)	0.0240 (9)	0.0009 (8)
C11	0.0677 (14)	0.0519 (12)	0.0604 (13)	−0.0086 (10)	0.0248 (11)	0.0089 (10)
C13	0.0490 (11)	0.0567 (12)	0.0655 (14)	0.0042 (9)	0.0174 (10)	−0.0053 (10)
C12	0.0619 (13)	0.0487 (12)	0.0705 (15)	−0.0001 (10)	0.0141 (11)	0.0084 (10)
C14	0.0474 (10)	0.0532 (11)	0.0479 (10)	−0.0036 (8)	0.0204 (8)	−0.0013 (8)

Geometric parameters (Å, º)

S1—C7	1.732 (2)	C4—H4	0.93
S1—C1	1.760 (2)	C5—C6	1.383 (3)
N1—C7	1.372 (2)	C5—H5	0.93
N1—C8	1.383 (2)	C8—C9	1.470 (3)
N1—C6	1.416 (2)	C9—C14	1.390 (3)
N2—C7	1.302 (3)	C9—C10	1.392 (3)
N2—N3	1.397 (2)	C10—C11	1.389 (3)
N3—C8	1.315 (2)	C10—H10	0.93
C1—C2	1.386 (3)	C11—C12	1.374 (3)
C1—C6	1.403 (3)	C11—H11	0.93
C2—C3	1.383 (3)	C13—C12	1.380 (4)
C2—H2	0.93	C13—C14	1.389 (3)
C3—C4	1.381 (3)	C13—H13	0.93
C3—H3	0.93	C12—H12	0.93
C4—C5	1.388 (3)	C14—H14	0.93
C7—S1—C1	88.98 (9)	N2—C7—N1	112.51 (17)
C7—N1—C8	103.94 (15)	N2—C7—S1	133.75 (15)
C7—N1—C6	113.54 (15)	N1—C7—S1	113.74 (14)
C8—N1—C6	142.42 (16)	N3—C8—N1	109.16 (16)
C7—N2—N3	105.37 (15)	N3—C8—C9	122.99 (16)
C8—N3—N2	109.01 (15)	N1—C8—C9	127.68 (16)
C2—C1—C6	120.21 (18)	C14—C9—C10	119.57 (19)
C2—C1—S1	126.18 (16)	C14—C9—C8	121.66 (16)
C6—C1—S1	113.52 (14)	C10—C9—C8	118.48 (17)
C3—C2—C1	118.9 (2)	C11—C10—C9	119.7 (2)
C3—C2—H2	120.5	C11—C10—H10	120.1
C1—C2—H2	120.5	C9—C10—H10	120.1
C4—C3—C2	120.42 (19)	C12—C11—C10	120.3 (2)
C4—C3—H3	119.8	C12—C11—H11	119.8
C2—C3—H3	119.8	C10—C11—H11	119.8
C3—C4—C5	121.6 (2)	C12—C13—C14	119.8 (2)
C3—C4—H4	119.2	C12—C13—H13	120.1
C5—C4—H4	119.2	C14—C13—H13	120.1
C6—C5—C4	117.95 (19)	C11—C12—C13	120.4 (2)
C6—C5—H5	121.0	C11—C12—H12	119.8
C4—C5—H5	121.0	C13—C12—H12	119.8
C5—C6—C1	120.81 (17)	C13—C14—C9	120.07 (19)
C5—C6—N1	129.05 (17)	C13—C14—H14	120.0
C1—C6—N1	110.05 (16)	C9—C14—H14	120.0
C7—N2—N3—C8	−0.8 (2)	C8—N1—C7—S1	178.29 (12)
C7—S1—C1—C2	176.40 (19)	C6—N1—C7—S1	−4.5 (2)
C7—S1—C1—C6	−0.29 (15)	C1—S1—C7—N2	−177.5 (2)
C6—C1—C2—C3	0.3 (3)	C1—S1—C7—N1	2.71 (15)
S1—C1—C2—C3	−176.22 (17)	N2—N3—C8—N1	−0.2 (2)
C1—C2—C3—C4	1.4 (4)	N2—N3—C8—C9	175.34 (16)
C2—C3—C4—C5	−1.2 (4)	C7—N1—C8—N3	1.0 (2)
C3—C4—C5—C6	−0.9 (3)	C6—N1—C8—N3	−174.8 (2)
C4—C5—C6—C1	2.6 (3)	C7—N1—C8—C9	−174.27 (17)
C4—C5—C6—N1	178.54 (18)	C6—N1—C8—C9	10.0 (4)
C2—C1—C6—C5	−2.4 (3)	N3—C8—C9—C14	−138.90 (19)
S1—C1—C6—C5	174.56 (15)	N1—C8—C9—C14	35.7 (3)
C2—C1—C6—N1	−178.98 (17)	N3—C8—C9—C10	34.7 (3)
S1—C1—C6—N1	−2.1 (2)	N1—C8—C9—C10	−150.63 (19)
C7—N1—C6—C5	−172.12 (19)	C14—C9—C10—C11	1.0 (3)
C8—N1—C6—C5	3.4 (4)	C8—C9—C10—C11	−172.78 (18)
C7—N1—C6—C1	4.1 (2)	C9—C10—C11—C12	−2.1 (3)
C8—N1—C6—C1	179.7 (2)	C10—C11—C12—C13	0.7 (4)
N3—N2—C7—N1	1.4 (2)	C14—C13—C12—C11	1.8 (4)
N3—N2—C7—S1	−178.32 (17)	C12—C13—C14—C9	−2.9 (3)
C8—N1—C7—N2	−1.5 (2)	C10—C9—C14—C13	1.5 (3)
C6—N1—C7—N2	175.68 (16)	C8—C9—C14—C13	175.05 (18)