





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810022506/lh5067sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810022506/lh5067Isup2.hkl |
CCDC reference: 786621
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.085
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1 PLAT793_ALERT_4_G The Model has Chirality at C7 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
0.01 mol of N'-(4-bromobenzylidine)pyridine-3-carbohydrazide was reacted with 0.03 mol of mercaptoacetic acid in anhydrous benzene for 8 h using a Dean-Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The separated solid was filtered, washed with water and crystallized from methanol. White crystalline solid. Yield: 60.84%; m.p.: 446.1–450.0 K. UV (EtOH) max: 202.6, 221.2, 264.8 nm. IR (KBr) υ: 1666 (amide C=O), 1687 (thia C=O); 1H-NMR (DMSO-d6, 400 MHz): 3.80 (1H, d, J=16 Hz, H5-thia.), 3.95 (1H, dd, J=15.8, 2.8 Hz, H5-thia.), 5.92 (1H, s, H2-thia.), 7.46 (2H, d, J=8.4 Hz, 2-C6H4-(H2,6)-thia.), 7.47–7.49 (1H, m, H5-pyridine), 7.56 (1H, d, J=8.8 Hz, 2-C6H4-(H3,5)-thia.), 8.08 (1H, dt, J=8.4, 1.6, 1.6 Hz, H4-pyridine), 8.71 (1H, dd, J=4.6, 1.6 Hz, H6-pyridine), 8.87 (1H, d, J=1.6 Hz, H2-pyridine), 10.93 (1H, s, CONH); ESI+ (m/z): 380.23 ([MH+2]+, 100), 378.24([MH]+, 98.71). Analysis calculated for C15H12BrN3O2S: C 47.63, H 3.20, N 11.11%. Found: C 47.39, H 3.09, N 10.98%.
The C-bound H atoms were geometrically placed (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The N-bound H atoms were located from the Fourier synthesis and restrained to 0.86 (2) Å, and refined with Uiso(H) = 1.5Ueq(N).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H12BrN3O2S | Dx = 1.637 Mg m−3 |
Mr = 378.25 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 10912 reflections |
Hall symbol: -R 3 | θ = 1.6–28.0° |
a = 24.9588 (9) Å | µ = 2.82 mm−1 |
c = 12.8013 (5) Å | T = 296 K |
V = 6906.1 (4) Å3 | Block, colourless |
Z = 18 | 0.28 × 0.23 × 0.19 mm |
F(000) = 3420 |
Stoe IPDS 2 diffractometer | 3174 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1963 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.6° |
ω scans | h = −30→27 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −31→31 |
Tmin = 0.505, Tmax = 0.616 | l = −15→16 |
13554 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3 |
3174 reflections | (Δ/σ)max < 0.001 |
202 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.35 e Å−3 |
C15H12BrN3O2S | Z = 18 |
Mr = 378.25 | Mo Kα radiation |
Trigonal, R3 | µ = 2.82 mm−1 |
a = 24.9588 (9) Å | T = 296 K |
c = 12.8013 (5) Å | 0.28 × 0.23 × 0.19 mm |
V = 6906.1 (4) Å3 |
Stoe IPDS 2 diffractometer | 3174 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1963 reflections with I > 2σ(I) |
Tmin = 0.505, Tmax = 0.616 | Rint = 0.050 |
13554 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.22 e Å−3 |
3174 reflections | Δρmin = −0.35 e Å−3 |
202 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Br1 | 0.04324 (2) | 0.93003 (2) | 0.13333 (3) | 0.0833 (2) | |
S1 | 0.18291 (4) | 0.97254 (4) | 0.63617 (6) | 0.0594 (3) | |
O1 | 0.35556 (11) | 1.03443 (11) | 0.58153 (16) | 0.0609 (9) | |
O2 | 0.33205 (10) | 1.15286 (10) | 0.51669 (15) | 0.0561 (8) | |
N1 | 0.27161 (11) | 1.03012 (11) | 0.50268 (17) | 0.0459 (8) | |
N2 | 0.30533 (11) | 1.06767 (12) | 0.41953 (17) | 0.0456 (8) | |
N3 | 0.41259 (16) | 1.17793 (16) | 0.1703 (2) | 0.0802 (13) | |
C1 | 0.16764 (13) | 0.99737 (13) | 0.4306 (2) | 0.0403 (9) | |
C2 | 0.16483 (14) | 0.95013 (14) | 0.3696 (2) | 0.0496 (11) | |
C3 | 0.12676 (15) | 0.92888 (15) | 0.2825 (2) | 0.0533 (11) | |
C4 | 0.09162 (14) | 0.95549 (15) | 0.2568 (2) | 0.0522 (11) | |
C5 | 0.09214 (14) | 1.00079 (15) | 0.3177 (2) | 0.0534 (11) | |
C6 | 0.13042 (14) | 1.02166 (14) | 0.4045 (2) | 0.0474 (10) | |
C7 | 0.21047 (13) | 1.02331 (14) | 0.5225 (2) | 0.0444 (10) | |
C8 | 0.30194 (16) | 1.02317 (14) | 0.5850 (2) | 0.0488 (11) | |
C9 | 0.26115 (15) | 1.00121 (17) | 0.6800 (2) | 0.0610 (11) | |
C10 | 0.33513 (13) | 1.13027 (15) | 0.4341 (2) | 0.0443 (10) | |
C11 | 0.37035 (14) | 1.16854 (14) | 0.3424 (2) | 0.0451 (10) | |
C12 | 0.39270 (18) | 1.23136 (16) | 0.3450 (3) | 0.0687 (14) | |
C13 | 0.4255 (2) | 1.26670 (18) | 0.2588 (3) | 0.0816 (16) | |
C14 | 0.43328 (19) | 1.2376 (2) | 0.1757 (3) | 0.0802 (17) | |
C15 | 0.38243 (17) | 1.14490 (17) | 0.2539 (3) | 0.0653 (14) | |
H2 | 0.18870 | 0.93250 | 0.38740 | 0.0600* | |
H2A | 0.3055 (19) | 1.0477 (17) | 0.366 (2) | 0.1000* | |
H3 | 0.12500 | 0.89710 | 0.24190 | 0.0640* | |
H5 | 0.06710 | 1.01740 | 0.30110 | 0.0640* | |
H6 | 0.13100 | 1.05260 | 0.44590 | 0.0570* | |
H7 | 0.21550 | 1.06370 | 0.54110 | 0.0530* | |
H9A | 0.27310 | 1.03500 | 0.72880 | 0.0730* | |
H9B | 0.26480 | 0.96860 | 0.71470 | 0.0730* | |
H12 | 0.38610 | 1.24980 | 0.40290 | 0.0820* | |
H13 | 0.44160 | 1.30930 | 0.25830 | 0.0980* | |
H14 | 0.45490 | 1.26170 | 0.11850 | 0.0960* | |
H15 | 0.36840 | 1.10270 | 0.25250 | 0.0780* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0755 (3) | 0.1114 (4) | 0.0638 (2) | 0.0473 (3) | −0.0204 (2) | −0.0167 (2) |
S1 | 0.0544 (5) | 0.0724 (6) | 0.0463 (4) | 0.0279 (5) | 0.0077 (4) | 0.0159 (4) |
O1 | 0.0534 (15) | 0.0774 (17) | 0.0589 (13) | 0.0380 (13) | −0.0050 (11) | 0.0014 (11) |
O2 | 0.0534 (14) | 0.0621 (14) | 0.0462 (12) | 0.0240 (12) | 0.0031 (9) | −0.0101 (10) |
N1 | 0.0430 (14) | 0.0531 (16) | 0.0386 (12) | 0.0218 (13) | 0.0041 (11) | 0.0096 (11) |
N2 | 0.0462 (15) | 0.0478 (16) | 0.0370 (13) | 0.0192 (13) | 0.0057 (11) | 0.0030 (11) |
N3 | 0.095 (3) | 0.068 (2) | 0.0646 (18) | 0.031 (2) | 0.0335 (17) | 0.0100 (16) |
C1 | 0.0415 (17) | 0.0418 (17) | 0.0388 (14) | 0.0217 (14) | 0.0059 (12) | 0.0077 (12) |
C2 | 0.0474 (19) | 0.052 (2) | 0.0564 (17) | 0.0300 (16) | 0.0032 (14) | 0.0058 (14) |
C3 | 0.053 (2) | 0.052 (2) | 0.0570 (18) | 0.0278 (17) | 0.0042 (15) | −0.0056 (15) |
C4 | 0.0463 (19) | 0.058 (2) | 0.0486 (16) | 0.0233 (17) | 0.0024 (14) | 0.0021 (15) |
C5 | 0.0477 (19) | 0.056 (2) | 0.0630 (19) | 0.0309 (17) | −0.0008 (15) | 0.0061 (16) |
C6 | 0.0514 (19) | 0.0434 (18) | 0.0514 (16) | 0.0268 (16) | 0.0050 (14) | 0.0040 (13) |
C7 | 0.0421 (18) | 0.0465 (18) | 0.0456 (15) | 0.0229 (15) | 0.0027 (13) | 0.0031 (13) |
C8 | 0.058 (2) | 0.0515 (19) | 0.0404 (16) | 0.0299 (17) | −0.0024 (14) | −0.0005 (13) |
C9 | 0.064 (2) | 0.076 (2) | 0.0430 (17) | 0.035 (2) | −0.0016 (15) | 0.0114 (16) |
C10 | 0.0359 (16) | 0.053 (2) | 0.0425 (16) | 0.0212 (15) | −0.0028 (12) | −0.0033 (14) |
C11 | 0.0401 (17) | 0.0482 (19) | 0.0452 (16) | 0.0207 (15) | −0.0005 (13) | 0.0004 (13) |
C12 | 0.080 (3) | 0.056 (2) | 0.058 (2) | 0.025 (2) | 0.0008 (18) | −0.0047 (17) |
C13 | 0.098 (3) | 0.044 (2) | 0.078 (3) | 0.017 (2) | 0.006 (2) | 0.0110 (19) |
C14 | 0.078 (3) | 0.071 (3) | 0.070 (3) | 0.021 (2) | 0.021 (2) | 0.011 (2) |
C15 | 0.076 (3) | 0.057 (2) | 0.0571 (19) | 0.029 (2) | 0.0231 (17) | 0.0053 (17) |
Br1—C4 | 1.896 (3) | C5—C6 | 1.386 (4) |
S1—C7 | 1.823 (3) | C8—C9 | 1.503 (4) |
S1—C9 | 1.801 (4) | C10—C11 | 1.491 (4) |
O1—C8 | 1.223 (5) | C11—C12 | 1.377 (5) |
O2—C10 | 1.219 (3) | C11—C15 | 1.379 (5) |
N1—N2 | 1.390 (3) | C12—C13 | 1.394 (6) |
N1—C7 | 1.471 (5) | C13—C14 | 1.356 (6) |
N1—C8 | 1.358 (4) | C2—H2 | 0.9300 |
N2—C10 | 1.366 (4) | C3—H3 | 0.9300 |
N3—C14 | 1.312 (6) | C5—H5 | 0.9300 |
N3—C15 | 1.331 (5) | C6—H6 | 0.9300 |
N2—H2A | 0.85 (3) | C7—H7 | 0.9800 |
C1—C6 | 1.380 (5) | C9—H9A | 0.9700 |
C1—C7 | 1.501 (4) | C9—H9B | 0.9700 |
C1—C2 | 1.386 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.387 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.379 (5) | C14—H14 | 0.9300 |
C4—C5 | 1.368 (4) | C15—H15 | 0.9300 |
Br1···H5i | 3.1900 | C15···O1vi | 3.399 (5) |
S1···C6ii | 3.524 (4) | C1···H6ii | 2.9800 |
S1···N3iii | 3.003 (3) | C2···H7ii | 2.7800 |
S1···C14iii | 3.644 (5) | C3···H7ii | 2.9100 |
S1···H6ii | 3.0300 | C4···H14viii | 3.0000 |
O1···N2 | 2.757 (4) | C5···H5i | 3.0700 |
O1···C10 | 3.281 (4) | C5···H14viii | 2.9100 |
O1···N2iv | 2.914 (4) | C6···H14viii | 3.0100 |
O1···C2iv | 3.369 (4) | C6···H6ii | 2.9700 |
O1···C15iv | 3.399 (6) | C8···H2Aiv | 3.00 (6) |
O2···C2v | 3.415 (6) | C10···H3iv | 2.9500 |
O2···C8 | 3.062 (4) | C10···H7 | 2.9300 |
O2···N1 | 2.659 (3) | C12···H9Bv | 3.0200 |
O2···C7 | 3.140 (4) | C15···H2A | 2.64 (4) |
O2···C3iv | 3.237 (6) | H2···N1 | 2.7100 |
O1···H15iv | 2.5000 | H2···O2ii | 2.7500 |
O1···H2Aiv | 2.07 (5) | H2A···C15 | 2.64 (4) |
O2···H7 | 2.6500 | H2A···H15 | 2.0700 |
O2···H2v | 2.7500 | H2A···O1vi | 2.07 (3) |
O2···H12 | 2.5600 | H2A···C8vi | 3.00 (4) |
O2···H3iv | 2.4300 | H3···O2vi | 2.4300 |
N1···O2 | 2.659 (3) | H3···C10vi | 2.9500 |
N2···O1 | 2.757 (4) | H5···Br1ix | 3.1900 |
N2···C2 | 3.320 (4) | H5···C5ix | 3.0700 |
N2···O1vi | 2.914 (4) | H6···H7 | 2.3300 |
N3···C9vii | 3.262 (5) | H6···S1v | 3.0300 |
N3···S1vii | 3.003 (3) | H6···C1v | 2.9800 |
N1···H2 | 2.7100 | H6···C6v | 2.9700 |
N2···H15 | 2.5400 | H7···O2 | 2.6500 |
N3···H9Bvii | 2.8500 | H7···C10 | 2.9300 |
C2···N2 | 3.320 (4) | H7···H6 | 2.3300 |
C2···O2ii | 3.415 (4) | H7···C2v | 2.7800 |
C2···O1vi | 3.369 (5) | H7···C3v | 2.9100 |
C3···O2vi | 3.237 (5) | H9B···C12ii | 3.0200 |
C6···S1v | 3.524 (3) | H9B···N3iii | 2.8500 |
C7···O2 | 3.140 (4) | H12···O2 | 2.5600 |
C8···O2 | 3.062 (4) | H14···C4viii | 3.0000 |
C9···N3iii | 3.262 (5) | H14···C5viii | 2.9100 |
C10···O1 | 3.281 (4) | H14···C6viii | 3.0100 |
C14···S1vii | 3.644 (4) | H15···N2 | 2.5400 |
C14···C15viii | 3.507 (7) | H15···H2A | 2.0700 |
C15···C14viii | 3.507 (7) | H15···O1vi | 2.5000 |
C7—S1—C9 | 90.87 (15) | C10—C11—C15 | 123.9 (3) |
N2—N1—C7 | 117.0 (2) | C11—C12—C13 | 118.5 (3) |
N2—N1—C8 | 119.5 (3) | C12—C13—C14 | 118.6 (4) |
C7—N1—C8 | 117.6 (2) | N3—C14—C13 | 124.7 (4) |
N1—N2—C10 | 117.8 (2) | N3—C15—C11 | 124.9 (3) |
C14—N3—C15 | 116.1 (3) | C1—C2—H2 | 120.00 |
C10—N2—H2A | 129 (2) | C3—C2—H2 | 120.00 |
N1—N2—H2A | 114 (2) | C2—C3—H3 | 120.00 |
C2—C1—C7 | 122.0 (3) | C4—C3—H3 | 120.00 |
C2—C1—C6 | 118.6 (3) | C4—C5—H5 | 120.00 |
C6—C1—C7 | 119.4 (3) | C6—C5—H5 | 120.00 |
C1—C2—C3 | 120.8 (3) | C1—C6—H6 | 119.00 |
C2—C3—C4 | 119.1 (3) | C5—C6—H6 | 119.00 |
C3—C4—C5 | 121.1 (3) | S1—C7—H7 | 109.00 |
Br1—C4—C3 | 119.3 (2) | N1—C7—H7 | 109.00 |
Br1—C4—C5 | 119.6 (3) | C1—C7—H7 | 109.00 |
C4—C5—C6 | 119.2 (3) | S1—C9—H9A | 110.00 |
C1—C6—C5 | 121.2 (3) | S1—C9—H9B | 110.00 |
S1—C7—C1 | 112.7 (2) | C8—C9—H9A | 110.00 |
S1—C7—N1 | 103.1 (2) | C8—C9—H9B | 110.00 |
N1—C7—C1 | 112.9 (2) | H9A—C9—H9B | 109.00 |
N1—C8—C9 | 110.8 (3) | C11—C12—H12 | 121.00 |
O1—C8—C9 | 125.3 (3) | C13—C12—H12 | 121.00 |
O1—C8—N1 | 123.9 (3) | C12—C13—H13 | 121.00 |
S1—C9—C8 | 107.2 (2) | C14—C13—H13 | 121.00 |
N2—C10—C11 | 115.8 (2) | N3—C14—H14 | 118.00 |
O2—C10—N2 | 121.6 (3) | C13—C14—H14 | 118.00 |
O2—C10—C11 | 122.7 (3) | N3—C15—H15 | 118.00 |
C12—C11—C15 | 117.2 (3) | C11—C15—H15 | 118.00 |
C10—C11—C12 | 118.9 (3) | ||
C7—S1—C9—C8 | −26.5 (3) | C7—C1—C2—C3 | −177.2 (3) |
C9—S1—C7—N1 | 29.0 (2) | C6—C1—C7—S1 | 104.9 (3) |
C9—S1—C7—C1 | 151.0 (3) | C6—C1—C7—N1 | −138.8 (3) |
C7—N1—N2—C10 | 78.1 (4) | C1—C2—C3—C4 | 0.2 (5) |
C8—N1—C7—S1 | −26.4 (3) | C2—C3—C4—C5 | −2.3 (5) |
N2—N1—C7—C1 | 58.8 (3) | C2—C3—C4—Br1 | 176.3 (2) |
N2—N1—C7—S1 | −179.29 (19) | Br1—C4—C5—C6 | −176.3 (2) |
N2—N1—C8—O1 | −19.3 (4) | C3—C4—C5—C6 | 2.4 (5) |
C7—N1—C8—O1 | −171.5 (3) | C4—C5—C6—C1 | −0.3 (5) |
N2—N1—C8—C9 | 159.6 (3) | O1—C8—C9—S1 | −165.2 (3) |
C7—N1—C8—C9 | 7.4 (4) | N1—C8—C9—S1 | 16.0 (3) |
C8—N1—C7—C1 | −148.3 (3) | N2—C10—C11—C12 | 169.1 (4) |
C8—N1—N2—C10 | −74.3 (4) | O2—C10—C11—C12 | −9.9 (6) |
N1—N2—C10—O2 | −0.7 (5) | O2—C10—C11—C15 | 169.9 (4) |
N1—N2—C10—C11 | −179.7 (3) | N2—C10—C11—C15 | −11.1 (6) |
C14—N3—C15—C11 | 1.9 (7) | C15—C11—C12—C13 | 0.3 (6) |
C15—N3—C14—C13 | −0.6 (8) | C10—C11—C15—N3 | 178.5 (4) |
C6—C1—C2—C3 | 1.8 (5) | C10—C11—C12—C13 | −179.9 (4) |
C2—C1—C6—C5 | −1.7 (5) | C12—C11—C15—N3 | −1.8 (7) |
C2—C1—C7—N1 | 40.2 (4) | C11—C12—C13—C14 | 0.8 (7) |
C7—C1—C6—C5 | 177.3 (3) | C12—C13—C14—N3 | −0.7 (8) |
C2—C1—C7—S1 | −76.2 (3) |
Symmetry codes: (i) −x+y−1, −x+1, z; (ii) y−1, −x+y, −z+1; (iii) −y+4/3, x−y+5/3, z+2/3; (iv) −x+y−1/3, −x+4/3, z+1/3; (v) x−y+1, x+1, −z+1; (vi) −y+4/3, x−y+5/3, z−1/3; (vii) −x+y−1/3, −x+4/3, z−2/3; (viii) −x+2/3, −y+7/3, −z+1/3; (ix) −y+1, x−y+2, z. |
Cg3 is the centroid of the C1–C6 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1vi | 0.85 (3) | 2.07 (3) | 2.914 (4) | 172 (4) |
C3—H3···O2vi | 0.93 | 2.43 | 3.237 (5) | 146 |
C15—H15···N2 | 0.93 | 2.54 | 2.864 (5) | 101 |
C15—H15···O1vi | 0.93 | 2.50 | 3.399 (5) | 162 |
C14—H14···Cg3x | 0.93 | 2.79 | 3.692 (4) | 164 |
Symmetry codes: (vi) −y+4/3, x−y+5/3, z−1/3; (x) x+1, y, z+2. |
Experimental details
Crystal data | |
Chemical formula | C15H12BrN3O2S |
Mr | 378.25 |
Crystal system, space group | Trigonal, R3 |
Temperature (K) | 296 |
a, c (Å) | 24.9588 (9), 12.8013 (5) |
V (Å3) | 6906.1 (4) |
Z | 18 |
Radiation type | Mo Kα |
µ (mm−1) | 2.82 |
Crystal size (mm) | 0.28 × 0.23 × 0.19 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.505, 0.616 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13554, 3174, 1963 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.085, 0.95 |
No. of reflections | 3174 |
No. of parameters | 202 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.35 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
Cg3 is the centroid of the C1–C6 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.85 (3) | 2.07 (3) | 2.914 (4) | 172 (4) |
C3—H3···O2i | 0.93 | 2.43 | 3.237 (5) | 146 |
C15—H15···N2 | 0.93 | 2.54 | 2.864 (5) | 101 |
C15—H15···O1i | 0.93 | 2.50 | 3.399 (5) | 162 |
C14—H14···Cg3ii | 0.93 | 2.79 | 3.692 (4) | 164 |
Symmetry codes: (i) −y+4/3, x−y+5/3, z−1/3; (ii) x+1, y, z+2. |
Development of new active compounds for viral infections is a high priority goal. The rapid onset of resistance and hypersensitivity reactions limit the use of antiviral compounds and therefore, there is an ongoing need for novel antiviral agents. A number of diverse chemical structures have been shown to be potent RT Inhibitors. Nicotinamide is gaining attention for its cytoprotective and antiviral properties (Gaudineau et al., 2004). Antiviral effect of nicotinamide and its inhibitory effect on enterovirus induced chemokine secretion have been recently shown (Moell et al., 2009). Furthermore, 3-pyridinecarboxamide derivatives with antitumor activity have been reported (Elbaum et al., 2003). Thiazolidinones exhibit various biological activities such as antifungal (Capan et al., 1999; Ozkırımlı et al., 2009); antituberculosis (Guzel et al., 2006); RT Inhibitor (Rawal et al., 2007); antiviral (Vanderlinden et al., 2010). We combine these two moities as part of an ongoing project directed towards the design and synthesis of bioactive molecules bearing 4-thiazolidinone and pyridine-3-carboxamide scaffolds together.
In the title molecule (I) shown in Fig. 1, the bond lengths and the bond angles are in the normal ranges (Allen et al., 1987). The C2—C1—C7—N1, C2—C1—C7—S1, N1—N2—C10—O2 and N1—N2—C10—C11 torsion angles are 40.2 (4), -76.2 (3), -0.7 (5) and -179.7 (3) °, respectively. The dihedral angle between the pyridine (N3/C11–C15) and benzene (C1–C6) rings is 73.17 (19) °. The five-membered 1,3-thiazolidine ring has an envelope conformation, with atom S1 displaced by -0.196 (1) Å from the S1/N1/C7–C9 plane [the puckering parameters (Cremer & Pople, 1975) are Q2 = 0.361 (3) Å and ϕ2 = 188.0 (5) °].
The crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2) and a C—H···π interactions (Table 1). A weak π-π stacking interaction is observed between the 1,3-thiazolidine and pyridine rings [Cg2···Cg2(2/3 - x, 7/3 - y, 1/3 - z) = 3.805 (2) Å, where Cg1 and Cg2 are the centroids of the S1/N1/C7–C9 1,3-thiazolidine and N3/C11–C15 pyridine rings, respectively].