2-(2-Bromo-5-methoxy­phenyl)-6-phenyl-1,3-thia­zolo[3,2-b][1,2,4]triazole

The mol­ecule of the title compound, C₁₇H₁₂BrN₃OS, is essentially planar. Geometric parameters are in the normal ranges. There are two intra­molecular C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.087
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-(2-Bromo-5-methoxyphenyl)-6-phenyl-1,3-thiazolo[3,2-b][1,2,4]triazole

Crystal data

C17H12BrN3OS	F(000) = 1552
Mr = 386.27	Dx = 1.669 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8171 reflections
a = 14.9271 (13) Å	θ = 3.5–25.9°
b = 10.9247 (13) Å	µ = 2.82 mm^−1
c = 18.8582 (16) Å	T = 173 K
V = 3075.3 (5) Å^3	Plate, colourless
Z = 8	0.32 × 0.16 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer	2883 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −18→18
Tmin = 0.466, Tmax = 0.806	k = −13→11
10330 measured reflections	l = −22→19

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0505P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
2883 reflections	Δρmax = 0.55 e Å^−3
210 parameters	Δρmin = −0.80 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (4)

Special details

Experimental. Spectroscopic data: IR (KBr, ν, cm-1): 3118 and 3070 (–CH), 1475 (–C═ N–), 734 (C—Br); ¹H NMR (300 MHz, DMSO-d₆, δ, p.p.m.): 3.8 (s, 3H, –OCH₃), 7.03 (dd, J = 8.7 Hz, 1H, ArH), 7.44 (s, 1H, ArH), 7.55 (m, 3H, ArH), 7.67 (d, J = 8.7 Hz, 1H, ArH), 8.01 (s, 1H, ArH), 8.27 (d, J = 7.8 Hz, 1H, NH); ¹³C NMR (75 MHz, DMSO-d₆, δ, p.p.m.): 55.62, 111.14, 111.47, 116.96, 117.31, 126.27, 127.57, 129.00, 129.69, 131.52, 132.57, 134.66, 158.43; DEPT: 55.64, 111.16, 116.98, 117.34, 126.29, 129.04, 129.73, 134.68; FAB-MS: m/z 386 (I = 100%, M+), 387 (I = 20%, M+1), 388 (I = 95%, M+2).

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
Br1	0.51020 (2)	0.22648 (3)	0.601791 (16)	0.02619 (14)
S1	0.24276 (6)	0.65017 (9)	0.44150 (4)	0.0305 (2)
C2	0.2341 (2)	0.6757 (3)	0.53258 (17)	0.0252 (7)
H2	0.1955	0.7360	0.5522	0.030*
C3	0.28695 (19)	0.6025 (3)	0.57326 (16)	0.0189 (6)
N4	0.33621 (16)	0.5240 (2)	0.52838 (13)	0.0167 (5)
C5	0.3208 (2)	0.5366 (3)	0.45748 (16)	0.0201 (7)
N6	0.39689 (16)	0.4322 (2)	0.53952 (13)	0.0176 (5)
C7	0.41417 (19)	0.3955 (3)	0.47251 (15)	0.0160 (6)
N8	0.36851 (17)	0.4577 (3)	0.42021 (14)	0.0220 (6)
C11	0.2932 (2)	0.6004 (3)	0.65120 (16)	0.0199 (7)
C12	0.3503 (2)	0.5207 (3)	0.68784 (16)	0.0238 (7)
H12	0.3877	0.4658	0.6623	0.029*
C13	0.3523 (2)	0.5218 (3)	0.76212 (18)	0.0281 (8)
H13	0.3909	0.4672	0.7868	0.034*
C14	0.2984 (2)	0.6020 (4)	0.79987 (17)	0.0289 (8)
H14	0.3001	0.6024	0.8502	0.035*
C15	0.2420 (2)	0.6815 (4)	0.76413 (18)	0.0310 (8)
H15	0.2049	0.7362	0.7900	0.037*
C16	0.2397 (2)	0.6812 (3)	0.69055 (18)	0.0268 (7)
H16	0.2012	0.7366	0.6665	0.032*
C21	0.47465 (19)	0.2939 (3)	0.45363 (16)	0.0181 (6)
C22	0.51916 (19)	0.2133 (3)	0.50081 (17)	0.0217 (7)
C23	0.5720 (2)	0.1191 (3)	0.47531 (18)	0.0267 (8)
H23	0.6018	0.0669	0.5079	0.032*
C24	0.5824 (2)	0.0991 (3)	0.40270 (18)	0.0257 (7)
H24	0.6186	0.0336	0.3860	0.031*
C25	0.5392 (2)	0.1763 (3)	0.35519 (16)	0.0216 (7)
C26	0.4867 (2)	0.2723 (3)	0.38048 (17)	0.0199 (6)
H26	0.4580	0.3250	0.3474	0.024*
O27	0.54298 (16)	0.1662 (2)	0.28269 (11)	0.0282 (5)
C27	0.5943 (2)	0.0665 (4)	0.25456 (19)	0.0332 (8)
H27A	0.6569	0.0748	0.2695	0.050*
H27B	0.5910	0.0676	0.2027	0.050*
H27C	0.5701	−0.0111	0.2723	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0293 (2)	0.0320 (2)	0.01726 (18)	0.00602 (14)	−0.00335 (12)	0.00285 (14)
S1	0.0350 (5)	0.0379 (5)	0.0187 (4)	0.0169 (4)	0.0011 (3)	0.0059 (4)
C2	0.0290 (17)	0.0259 (19)	0.0208 (16)	0.0071 (15)	0.0039 (13)	0.0016 (14)
C3	0.0168 (14)	0.0191 (16)	0.0207 (16)	0.0027 (13)	0.0039 (11)	−0.0013 (13)
N4	0.0177 (12)	0.0192 (14)	0.0132 (12)	0.0013 (11)	0.0003 (9)	0.0012 (10)
C5	0.0206 (15)	0.0247 (18)	0.0149 (15)	0.0029 (13)	−0.0001 (12)	0.0036 (13)
N6	0.0166 (12)	0.0181 (14)	0.0182 (13)	0.0019 (11)	0.0001 (10)	−0.0002 (10)
C7	0.0158 (13)	0.0185 (16)	0.0135 (14)	−0.0032 (12)	0.0005 (10)	0.0017 (12)
N8	0.0240 (14)	0.0254 (15)	0.0166 (13)	0.0074 (12)	0.0004 (10)	0.0014 (11)
C11	0.0203 (15)	0.0224 (17)	0.0169 (15)	−0.0017 (13)	0.0027 (11)	−0.0008 (13)
C12	0.0238 (16)	0.0313 (19)	0.0162 (15)	0.0012 (14)	0.0025 (13)	−0.0030 (14)
C13	0.0228 (16)	0.040 (2)	0.0220 (16)	0.0013 (15)	−0.0022 (13)	0.0017 (16)
C14	0.0284 (17)	0.043 (2)	0.0148 (15)	−0.0074 (16)	0.0003 (13)	−0.0061 (15)
C15	0.0314 (18)	0.037 (2)	0.0243 (17)	−0.0016 (16)	0.0050 (14)	−0.0091 (15)
C16	0.0267 (17)	0.0303 (19)	0.0234 (16)	0.0022 (15)	−0.0006 (13)	−0.0034 (14)
C21	0.0164 (14)	0.0188 (17)	0.0191 (15)	−0.0023 (13)	0.0020 (11)	−0.0019 (12)
C22	0.0168 (14)	0.0277 (19)	0.0205 (15)	0.0001 (14)	−0.0011 (11)	−0.0003 (13)
C23	0.0241 (17)	0.0269 (19)	0.0292 (18)	0.0058 (15)	−0.0038 (13)	0.0033 (15)
C24	0.0254 (16)	0.0234 (17)	0.0284 (18)	0.0065 (14)	0.0007 (13)	−0.0037 (15)
C25	0.0201 (15)	0.0244 (18)	0.0203 (16)	−0.0010 (14)	0.0018 (12)	−0.0020 (13)
C26	0.0193 (14)	0.0235 (16)	0.0169 (15)	−0.0018 (14)	−0.0007 (11)	0.0020 (12)
O27	0.0329 (13)	0.0329 (14)	0.0188 (11)	0.0080 (11)	0.0043 (9)	−0.0047 (10)
C27	0.0360 (19)	0.037 (2)	0.0265 (19)	0.0076 (17)	0.0017 (15)	−0.0074 (15)

Geometric parameters (Å, º)

Br1—C22	1.915 (3)	C14—C15	1.384 (5)
S1—C5	1.728 (3)	C14—H14	0.9500
S1—C2	1.745 (3)	C15—C16	1.388 (5)
C2—C3	1.361 (5)	C15—H15	0.9500
C2—H2	0.9500	C16—H16	0.9500
C3—N4	1.412 (4)	C21—C26	1.411 (4)
C3—C11	1.473 (4)	C21—C22	1.417 (4)
N4—C5	1.364 (4)	C22—C23	1.383 (5)
N4—N6	1.367 (3)	C23—C24	1.395 (5)
C5—N8	1.320 (4)	C23—H23	0.9500
N6—C7	1.351 (4)	C24—C25	1.389 (5)
C7—N8	1.378 (4)	C24—H24	0.9500
C7—C21	1.475 (4)	C25—O27	1.373 (4)
C11—C12	1.401 (5)	C25—C26	1.394 (5)
C11—C16	1.403 (5)	C26—H26	0.9500
C12—C13	1.401 (5)	O27—C27	1.434 (4)
C12—H12	0.9500	C27—H27A	0.9800
C13—C14	1.387 (5)	C27—H27B	0.9800
C13—H13	0.9500	C27—H27C	0.9800
C5—S1—C2	89.62 (15)	C14—C15—H15	120.0
C3—C2—S1	114.7 (3)	C16—C15—H15	120.0
C3—C2—H2	122.7	C15—C16—C11	121.0 (3)
S1—C2—H2	122.7	C15—C16—H16	119.5
C2—C3—N4	108.7 (3)	C11—C16—H16	119.5
C2—C3—C11	127.5 (3)	C26—C21—C22	116.8 (3)
N4—C3—C11	123.8 (3)	C26—C21—C7	116.1 (3)
C5—N4—N6	109.7 (2)	C22—C21—C7	127.1 (3)
C5—N4—C3	116.0 (3)	C23—C22—C21	120.8 (3)
N6—N4—C3	134.3 (3)	C23—C22—Br1	116.2 (2)
N8—C5—N4	111.4 (3)	C21—C22—Br1	123.0 (2)
N8—C5—S1	137.7 (2)	C22—C23—C24	121.4 (3)
N4—C5—S1	110.9 (2)	C22—C23—H23	119.3
C7—N6—N4	101.6 (2)	C24—C23—H23	119.3
N6—C7—N8	115.4 (3)	C25—C24—C23	119.1 (3)
N6—C7—C21	124.5 (3)	C25—C24—H24	120.5
N8—C7—C21	120.1 (3)	C23—C24—H24	120.5
C5—N8—C7	102.0 (2)	O27—C25—C24	125.1 (3)
C12—C11—C16	118.5 (3)	O27—C25—C26	115.1 (3)
C12—C11—C3	122.7 (3)	C24—C25—C26	119.8 (3)
C16—C11—C3	118.8 (3)	C25—C26—C21	122.1 (3)
C11—C12—C13	120.1 (3)	C25—C26—H26	119.0
C11—C12—H12	120.0	C21—C26—H26	119.0
C13—C12—H12	120.0	C25—O27—C27	116.8 (3)
C14—C13—C12	120.4 (3)	O27—C27—H27A	109.5
C14—C13—H13	119.8	O27—C27—H27B	109.5
C12—C13—H13	119.8	H27A—C27—H27B	109.5
C15—C14—C13	120.0 (3)	O27—C27—H27C	109.5
C15—C14—H14	120.0	H27A—C27—H27C	109.5
C13—C14—H14	120.0	H27B—C27—H27C	109.5
C14—C15—C16	120.1 (3)
C5—S1—C2—C3	−0.2 (3)	C3—C11—C12—C13	−179.1 (3)
S1—C2—C3—N4	0.4 (4)	C11—C12—C13—C14	−0.4 (5)
S1—C2—C3—C11	−178.7 (3)	C12—C13—C14—C15	0.1 (5)
C2—C3—N4—C5	−0.5 (4)	C13—C14—C15—C16	−0.2 (5)
C11—C3—N4—C5	178.6 (3)	C14—C15—C16—C11	0.6 (5)
C2—C3—N4—N6	−178.6 (3)	C12—C11—C16—C15	−0.9 (5)
C11—C3—N4—N6	0.6 (5)	C3—C11—C16—C15	178.9 (3)
N6—N4—C5—N8	−0.2 (4)	N6—C7—C21—C26	−177.7 (3)
C3—N4—C5—N8	−178.7 (3)	N8—C7—C21—C26	4.4 (4)
N6—N4—C5—S1	178.9 (2)	N6—C7—C21—C22	4.7 (5)
C3—N4—C5—S1	0.4 (3)	N8—C7—C21—C22	−173.2 (3)
C2—S1—C5—N8	178.6 (4)	C26—C21—C22—C23	0.4 (4)
C2—S1—C5—N4	−0.1 (3)	C7—C21—C22—C23	177.9 (3)
C5—N4—N6—C7	0.1 (3)	C26—C21—C22—Br1	−179.4 (2)
C3—N4—N6—C7	178.3 (3)	C7—C21—C22—Br1	−1.8 (4)
N4—N6—C7—N8	−0.1 (3)	C21—C22—C23—C24	−0.8 (5)
N4—N6—C7—C21	−178.1 (3)	Br1—C22—C23—C24	178.9 (3)
N4—C5—N8—C7	0.1 (3)	C22—C23—C24—C25	0.5 (5)
S1—C5—N8—C7	−178.6 (3)	C23—C24—C25—O27	−179.3 (3)
N6—C7—N8—C5	0.0 (3)	C23—C24—C25—C26	0.3 (5)
C21—C7—N8—C5	178.1 (3)	O27—C25—C26—C21	178.9 (3)
C2—C3—C11—C12	−180.0 (3)	C24—C25—C26—C21	−0.7 (5)
N4—C3—C11—C12	1.0 (5)	C22—C21—C26—C25	0.4 (4)
C2—C3—C11—C16	0.2 (5)	C7—C21—C26—C25	−177.5 (3)
N4—C3—C11—C16	−178.8 (3)	C24—C25—O27—C27	1.3 (5)
C16—C11—C12—C13	0.7 (5)	C26—C25—O27—C27	−178.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···N8	0.95	2.40	2.788 (4)	104
C12—H12···N6	0.95	2.35	3.040 (4)	129