Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027388/ob6579sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027388/ob6579Isup2.hkl |
CCDC reference: 287681
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.070
- wR factor = 0.180
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was supplied by Linhai Dongdong Chemical Factory. Crystals of (I) suitable for X-ray diffraction were grown from an acetone solution by slow evaporation.
H atoms bonded to N atoms were located from difference Fourier maps and included in the refinement based on the as-found N—H bond lengths, but their Uiso paramenters were refined [should these therefore have s.u. values in CIF?]. All other H atoms were placed in calculated positions with C—H = 0.96–0.98 Å and included in the refinement as riding, with Uiso(H) = 1.2Ueq(carrier atom).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C12H13N3O2S | Z = 2 |
Mr = 263.31 | F(000) = 276.00 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 6.714 (3) Å | Cell parameters from 5401 reflections |
b = 8.630 (4) Å | θ = 2.5–27.5° |
c = 11.403 (4) Å | µ = 0.26 mm−1 |
α = 98.640 (11)° | T = 296 K |
β = 102.57 (2)° | Block, colorless |
γ = 102.911 (12)° | 0.30 × 0.25 × 0.12 mm |
V = 614.7 (4) Å3 |
Rigaku R-AXIS RAPID diffractometer | 2055 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.085 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→8 |
Tmin = 0.921, Tmax = 0.969 | k = −11→11 |
4455 measured reflections | l = −14→14 |
2766 independent reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.070 | w = 4Fo2/[0.004Fo2 + 4σ(Fo2) + 0.5] |
wR(F2) = 0.180 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.50 e Å−3 |
2055 reflections | Δρmin = −0.64 e Å−3 |
163 parameters |
C12H13N3O2S | γ = 102.911 (12)° |
Mr = 263.31 | V = 614.7 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.714 (3) Å | Mo Kα radiation |
b = 8.630 (4) Å | µ = 0.26 mm−1 |
c = 11.403 (4) Å | T = 296 K |
α = 98.640 (11)° | 0.30 × 0.25 × 0.12 mm |
β = 102.57 (2)° |
Rigaku R-AXIS RAPID diffractometer | 2766 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2055 reflections with F2 > 2σ(F2) |
Tmin = 0.921, Tmax = 0.969 | Rint = 0.085 |
4455 measured reflections |
R[F2 > 2σ(F2)] = 0.070 | 163 parameters |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.50 e Å−3 |
2055 reflections | Δρmin = −0.64 e Å−3 |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.16127 (12) | 0.25485 (9) | −0.00281 (6) | 0.0326 (2) | |
O1 | −0.0069 (4) | 0.1381 (2) | −0.0917 (2) | 0.0457 (6) | |
O2 | 0.2973 (4) | 0.3788 (2) | −0.0420 (2) | 0.0397 (6) | |
N1 | 0.3091 (5) | 0.1586 (3) | 0.0665 (2) | 0.0403 (7) | |
N2 | −0.2537 (4) | 0.3297 (3) | 0.1840 (2) | 0.0432 (8) | |
N3 | 0.3634 (5) | 0.5754 (3) | 0.1919 (2) | 0.0430 (7) | |
C1 | 0.0518 (5) | 0.3516 (3) | 0.1037 (2) | 0.0310 (7) | |
C2 | −0.1524 (5) | 0.2773 (4) | 0.1052 (3) | 0.0372 (8) | |
C3 | −0.1419 (6) | 0.4649 (4) | 0.2668 (3) | 0.0456 (10) | |
C4 | 0.0602 (5) | 0.5494 (4) | 0.2734 (3) | 0.0424 (9) | |
C5 | 0.1632 (5) | 0.4954 (3) | 0.1886 (2) | 0.0345 (8) | |
C6 | 0.4878 (5) | 0.7142 (4) | 0.2824 (2) | 0.0355 (8) | |
C7 | 0.5637 (6) | 0.8578 (4) | 0.2487 (3) | 0.0446 (9) | |
C8 | 0.6917 (7) | 0.9897 (4) | 0.3376 (4) | 0.0528 (11) | |
C9 | 0.7386 (7) | 0.9779 (4) | 0.4582 (3) | 0.0519 (10) | |
C10 | 0.6606 (6) | 0.8343 (4) | 0.4936 (3) | 0.0455 (9) | |
C11 | 0.5419 (5) | 0.7029 (4) | 0.4042 (3) | 0.0404 (9) | |
C12 | 0.7181 (8) | 0.8196 (6) | 0.6250 (3) | 0.0662 (13) | |
H2 | −0.2283 | 0.1780 | 0.0432 | 0.044* | |
H3 | −0.2102 | 0.5067 | 0.3277 | 0.056* | |
H4 | 0.1311 | 0.6482 | 0.3367 | 0.049* | |
H7 | 0.5275 | 0.8658 | 0.1622 | 0.051* | |
H8 | 0.7502 | 1.0915 | 0.3141 | 0.059* | |
H9 | 0.8263 | 1.0735 | 0.5209 | 0.056* | |
H11 | 0.4900 | 0.5990 | 0.4268 | 0.049* | |
H121 | 0.7971 | 0.9239 | 0.6755 | 0.076* | |
H122 | 0.8020 | 0.7434 | 0.6343 | 0.076* | |
H123 | 0.5907 | 0.7823 | 0.6496 | 0.076* | |
H101 | 0.4206 | 0.2060 | 0.1279 | 0.048* | |
H102 | 0.2226 | 0.0910 | 0.0929 | 0.047* | |
H301 | 0.3852 | 0.5567 | 0.1200 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0304 (4) | 0.0320 (4) | 0.0291 (4) | −0.0032 (3) | 0.0088 (3) | 0.0028 (2) |
O1 | 0.0438 (15) | 0.0454 (13) | 0.0349 (11) | −0.0067 (12) | 0.0095 (11) | −0.0013 (10) |
O2 | 0.0382 (13) | 0.0394 (12) | 0.0365 (11) | −0.0042 (10) | 0.0145 (10) | 0.0071 (9) |
N1 | 0.0386 (17) | 0.0380 (14) | 0.0415 (14) | 0.0038 (12) | 0.0129 (13) | 0.0056 (11) |
N2 | 0.0286 (15) | 0.0486 (16) | 0.0541 (17) | 0.0092 (13) | 0.0137 (13) | 0.0132 (13) |
N3 | 0.0370 (16) | 0.0442 (15) | 0.0383 (14) | −0.0025 (13) | 0.0133 (13) | −0.0052 (12) |
C1 | 0.0280 (16) | 0.0332 (15) | 0.0330 (14) | 0.0094 (13) | 0.0074 (12) | 0.0096 (12) |
C2 | 0.0256 (16) | 0.0399 (16) | 0.0441 (17) | 0.0047 (14) | 0.0077 (14) | 0.0109 (14) |
C3 | 0.039 (2) | 0.051 (2) | 0.051 (2) | 0.0155 (17) | 0.0183 (16) | 0.0059 (16) |
C4 | 0.038 (2) | 0.0406 (17) | 0.0443 (18) | 0.0100 (15) | 0.0082 (15) | 0.0004 (14) |
C5 | 0.0334 (17) | 0.0328 (15) | 0.0363 (15) | 0.0076 (13) | 0.0091 (13) | 0.0059 (12) |
C6 | 0.0272 (16) | 0.0380 (16) | 0.0355 (15) | 0.0056 (13) | 0.0050 (13) | −0.0010 (12) |
C7 | 0.043 (2) | 0.0440 (18) | 0.0411 (17) | 0.0063 (16) | 0.0063 (16) | 0.0071 (14) |
C8 | 0.047 (2) | 0.0367 (18) | 0.065 (2) | −0.0001 (17) | 0.0073 (19) | 0.0083 (17) |
C9 | 0.048 (2) | 0.0392 (18) | 0.052 (2) | 0.0006 (17) | 0.0045 (18) | −0.0110 (15) |
C10 | 0.043 (2) | 0.049 (2) | 0.0404 (17) | 0.0129 (17) | 0.0080 (16) | 0.0007 (15) |
C11 | 0.0397 (19) | 0.0380 (17) | 0.0435 (17) | 0.0102 (15) | 0.0119 (15) | 0.0069 (14) |
C12 | 0.059 (2) | 0.086 (3) | 0.044 (2) | 0.021 (2) | −0.001 (2) | 0.002 (2) |
S1—O1 | 1.416 (2) | C9—C10 | 1.388 (5) |
S1—O2 | 1.436 (2) | C10—C11 | 1.363 (4) |
S1—N1 | 1.589 (3) | C10—C12 | 1.495 (5) |
S1—C1 | 1.752 (3) | N1—H101 | 0.875 |
N2—C2 | 1.325 (5) | N1—H102 | 0.863 |
N2—C3 | 1.336 (4) | N3—H301 | 0.861 |
N3—C5 | 1.356 (4) | C2—H2 | 0.980 |
N3—C6 | 1.416 (3) | C3—H3 | 0.980 |
C1—C2 | 1.382 (4) | C4—H4 | 0.980 |
C1—C5 | 1.395 (3) | C7—H7 | 0.980 |
C3—C4 | 1.369 (5) | C8—H8 | 0.980 |
C4—C5 | 1.389 (5) | C9—H9 | 0.980 |
C6—C7 | 1.374 (5) | C11—H11 | 0.980 |
C6—C11 | 1.381 (4) | C12—H123 | 0.960 |
C7—C8 | 1.378 (4) | C12—H122 | 0.960 |
C8—C9 | 1.367 (6) | C12—H121 | 0.960 |
O1···O1i | 3.403 (3) | H3···H123xii | 3.232 |
O1···N1i | 2.985 (3) | H3···H301vi | 3.347 |
O2···O2ii | 2.902 (3) | H3···H101vi | 3.311 |
O2···N2iii | 3.223 (4) | H4···C9vii | 3.496 |
O2···N3ii | 3.124 (4) | H4···H9vii | 2.608 |
O2···C2iii | 3.451 (4) | H4···H122v | 3.561 |
O2···C3iii | 3.161 (4) | H7···S1ii | 3.288 |
O2···C4iii | 3.392 (4) | H7···O1iii | 3.403 |
O2···C6ii | 3.438 (4) | H7···O1ii | 3.489 |
O2···C7ii | 3.310 (4) | H7···O2ii | 2.943 |
N1···O1i | 2.985 (3) | H7···N1xiii | 3.393 |
N1···N2iv | 2.890 (4) | H7···N1ii | 3.039 |
N1···C2iv | 3.439 (4) | H7···C2iii | 3.362 |
N1···C12v | 3.541 (5) | H7···H2xiv | 3.446 |
N2···O2iii | 3.223 (4) | H7···H2iii | 2.648 |
N2···N1vi | 2.890 (4) | H7···H101xiii | 3.233 |
N3···O2ii | 3.124 (4) | H7···H101ii | 3.381 |
C2···O2iii | 3.451 (4) | H7···H102xiii | 3.182 |
C2···N1vi | 3.439 (4) | H8···N2xiv | 2.711 |
C3···O2iii | 3.161 (4) | H8···C2xiv | 3.166 |
C4···O2iii | 3.392 (4) | H8···C3xiv | 3.294 |
C6···O2ii | 3.438 (4) | H8···C12vii | 3.581 |
C7···O2ii | 3.310 (4) | H8···C12viii | 3.369 |
C8···C12vii | 3.575 (7) | H8···H2xiv | 3.309 |
C9···C9viii | 3.349 (6) | H8···H3xiv | 3.511 |
C9···C10vii | 3.525 (6) | H8···H123vii | 2.827 |
C10···C9vii | 3.525 (6) | H8···H122viii | 2.912 |
C12···N1v | 3.541 (5) | H8···H121viii | 3.049 |
C12···C8vii | 3.575 (7) | H8···H101xiii | 3.154 |
S1···H7ii | 3.288 | H9···C4vii | 3.535 |
S1···H102i | 3.331 | H9···C8viii | 3.486 |
O1···H2i | 3.498 | H9···C9viii | 3.016 |
O1···H7iii | 3.403 | H9···C10vii | 3.509 |
O1···H7ii | 3.489 | H9···C10viii | 3.404 |
O1···H121ix | 2.849 | H9···H4vii | 2.608 |
O1···H101i | 3.486 | H9···H9viii | 2.983 |
O1···H102i | 2.170 | H9···H122viii | 3.585 |
O2···H3iii | 3.512 | H11···C11v | 3.463 |
O2···H7ii | 2.943 | H11···C12v | 3.478 |
O2···H301ii | 2.468 | H11···H3iv | 2.720 |
N1···H2iv | 3.144 | H11···H11v | 2.568 |
N1···H2i | 2.864 | H11···H123v | 3.165 |
N1···H7x | 3.393 | H11···H122v | 3.043 |
N1···H7ii | 3.039 | H123···N1v | 3.098 |
N1···H123v | 3.098 | H123···N2xii | 3.331 |
N1···H121v | 3.314 | H123···C7vii | 3.598 |
N2···H8xi | 2.711 | H123···C8vii | 3.032 |
N2···H123xii | 3.331 | H123···C9vii | 3.508 |
N2···H122v | 3.521 | H123···H3xii | 3.232 |
N2···H301vi | 3.468 | H123···H8vii | 2.827 |
N2···H101vi | 2.115 | H123···H11v | 3.165 |
N2···H102vi | 3.496 | H123···H101v | 2.543 |
N3···H3iv | 3.170 | H123···H102v | 2.866 |
C1···H122v | 3.222 | H122···N2v | 3.521 |
C2···H7iii | 3.362 | H122···C1v | 3.222 |
C2···H8xi | 3.166 | H122···C2v | 3.420 |
C2···H122v | 3.420 | H122···C3v | 3.321 |
C2···H301iii | 3.385 | H122···C4v | 3.125 |
C2···H101vi | 2.872 | H122···C5v | 3.105 |
C2···H102i | 3.484 | H122···C8viii | 3.573 |
C3···H8xi | 3.294 | H122···H4v | 3.561 |
C3···H122v | 3.321 | H122···H8viii | 2.912 |
C3···H301vi | 3.567 | H122···H9viii | 3.585 |
C3···H101vi | 3.180 | H122···H11v | 3.043 |
C4···H9vii | 3.535 | H122···H101v | 3.388 |
C4···H122v | 3.125 | H122···H102v | 3.277 |
C5···H122v | 3.105 | H121···O1xv | 2.849 |
C6···H3iv | 3.005 | H121···N1v | 3.314 |
C7···H2iii | 3.517 | H121···C7vii | 3.553 |
C7···H123vii | 3.598 | H121···C8vii | 3.502 |
C7···H121vii | 3.553 | H121···C8viii | 3.386 |
C8···H9viii | 3.486 | H121···H8viii | 3.049 |
C8···H123vii | 3.032 | H121···H101v | 3.141 |
C8···H122viii | 3.573 | H121···H102v | 2.694 |
C8···H121vii | 3.502 | H301···O2ii | 2.468 |
C8···H121viii | 3.386 | H301···N2iv | 3.468 |
C9···H4vii | 3.496 | H301···C2iii | 3.385 |
C9···H9viii | 3.016 | H301···C3iv | 3.567 |
C9···H123vii | 3.508 | H301···H2iii | 3.366 |
C10···H3iv | 3.539 | H301···H3iv | 3.347 |
C10···H9vii | 3.509 | H301···H301ii | 3.540 |
C10···H9viii | 3.404 | H101···O1i | 3.486 |
C11···H3iv | 2.800 | H101···N2iv | 2.115 |
C11···H11v | 3.463 | H101···C2iv | 2.872 |
C12···H8vii | 3.581 | H101···C3iv | 3.180 |
C12···H8viii | 3.369 | H101···C12v | 3.177 |
C12···H11v | 3.478 | H101···H2iv | 2.779 |
C12···H101v | 3.177 | H101···H2i | 3.391 |
C12···H102v | 3.109 | H101···H3iv | 3.311 |
H2···O1i | 3.498 | H101···H7x | 3.233 |
H2···N1vi | 3.144 | H101···H7ii | 3.381 |
H2···N1i | 2.864 | H101···H8x | 3.154 |
H2···C7iii | 3.517 | H101···H123v | 2.543 |
H2···H7xi | 3.446 | H101···H122v | 3.388 |
H2···H7iii | 2.648 | H101···H121v | 3.141 |
H2···H8xi | 3.309 | H102···S1i | 3.331 |
H2···H301iii | 3.366 | H102···O1i | 2.170 |
H2···H101vi | 2.779 | H102···N2iv | 3.496 |
H2···H101i | 3.391 | H102···C2i | 3.484 |
H2···H102i | 2.604 | H102···C12v | 3.109 |
H3···O2iii | 3.512 | H102···H2i | 2.604 |
H3···N3vi | 3.170 | H102···H7x | 3.182 |
H3···C6vi | 3.005 | H102···H123v | 2.866 |
H3···C10vi | 3.539 | H102···H122v | 3.277 |
H3···C11vi | 2.800 | H102···H121v | 2.694 |
H3···H8xi | 3.511 | H102···H102i | 3.168 |
H3···H11vi | 2.720 | ||
O1—S1—O2 | 119.25 (14) | C6—C11—C10 | 121.3 (3) |
O1—S1—N1 | 107.19 (15) | S1—N1—H101 | 123.3 |
O1—S1—C1 | 107.60 (16) | S1—N1—H102 | 103.0 |
O2—S1—N1 | 106.45 (16) | H101—N1—H102 | 107.8 |
O2—S1—C1 | 107.76 (14) | C5—N3—H301 | 110.3 |
N1—S1—C1 | 108.17 (16) | C6—N3—H301 | 121.5 |
C2—N2—C3 | 114.7 (3) | N2—C2—H2 | 117.3 |
C5—N3—C6 | 124.1 (3) | C1—C2—H2 | 117.5 |
S1—C1—C2 | 117.6 (2) | N2—C3—H3 | 117.2 |
S1—C1—C5 | 123.1 (2) | C4—C3—H3 | 117.5 |
C2—C1—C5 | 119.2 (3) | C3—C4—H4 | 120.2 |
N2—C2—C1 | 125.1 (2) | C5—C4—H4 | 120.1 |
N2—C3—C4 | 125.3 (4) | C6—C7—H7 | 120.2 |
C3—C4—C5 | 119.6 (2) | C8—C7—H7 | 120.5 |
N3—C5—C1 | 122.4 (3) | C7—C8—H8 | 119.8 |
N3—C5—C4 | 121.6 (2) | C9—C8—H8 | 120.2 |
C1—C5—C4 | 116.0 (3) | C8—C9—H9 | 119.3 |
N3—C6—C7 | 120.2 (2) | C10—C9—H9 | 119.5 |
N3—C6—C11 | 119.8 (3) | C6—C11—H11 | 119.2 |
C7—C6—C11 | 119.9 (2) | C10—C11—H11 | 119.5 |
C6—C7—C8 | 119.3 (3) | C10—C12—H123 | 109.0 |
C7—C8—C9 | 120.0 (3) | C10—C12—H122 | 110.0 |
C8—C9—C10 | 121.2 (3) | C10—C12—H121 | 109.4 |
C9—C10—C11 | 118.1 (3) | H123—C12—H122 | 109.5 |
C9—C10—C12 | 121.2 (3) | H123—C12—H121 | 109.5 |
C11—C10—C12 | 120.6 (3) | H122—C12—H121 | 109.5 |
O1—S1—C1—C2 | 16.2 (3) | C2—C1—C5—C4 | 2.8 (5) |
O1—S1—C1—C5 | −166.1 (2) | C5—C1—C2—N2 | −1.6 (5) |
O2—S1—C1—C2 | 146.0 (2) | N2—C3—C4—C5 | 0.4 (6) |
O2—S1—C1—C5 | −36.3 (3) | C3—C4—C5—N3 | −179.9 (2) |
N1—S1—C1—C2 | −99.3 (2) | C3—C4—C5—C1 | −2.3 (5) |
N1—S1—C1—C5 | 78.4 (3) | N3—C6—C7—C8 | −177.3 (4) |
C2—N2—C3—C4 | 1.0 (6) | N3—C6—C11—C10 | −179.7 (4) |
C3—N2—C2—C1 | −0.4 (5) | C7—C6—C11—C10 | 3.6 (6) |
C5—N3—C6—C7 | −121.2 (4) | C11—C6—C7—C8 | −0.7 (6) |
C5—N3—C6—C11 | 62.2 (5) | C6—C7—C8—C9 | −1.3 (7) |
C6—N3—C5—C1 | −174.8 (3) | C7—C8—C9—C10 | 0.5 (7) |
C6—N3—C5—C4 | 2.6 (5) | C8—C9—C10—C11 | 2.4 (7) |
S1—C1—C2—N2 | 176.2 (3) | C8—C9—C10—C12 | 177.8 (4) |
S1—C1—C5—N3 | 2.8 (5) | C9—C10—C11—C6 | −4.4 (6) |
S1—C1—C5—C4 | −174.8 (2) | C12—C10—C11—C6 | −179.9 (3) |
C2—C1—C5—N3 | −179.6 (3) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1; (vi) x−1, y, z; (vii) −x+1, −y+2, −z+1; (viii) −x+2, −y+2, −z+1; (ix) x−1, y−1, z−1; (x) x, y−1, z; (xi) x−1, y−1, z; (xii) −x, −y+1, −z+1; (xiii) x, y+1, z; (xiv) x+1, y+1, z; (xv) x+1, y+1, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···N2iv | 0.88 | 2.12 | 2.890 (4) | 147 |
N1—H102···O1i | 0.86 | 2.17 | 2.985 (3) | 157 |
N3—H301···O2 | 0.86 | 2.10 | 2.824 (3) | 142 |
N3—H301···O2ii | 0.86 | 2.47 | 3.124 (4) | 134 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C12H13N3O2S |
Mr | 263.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.714 (3), 8.630 (4), 11.403 (4) |
α, β, γ (°) | 98.640 (11), 102.57 (2), 102.911 (12) |
V (Å3) | 614.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.30 × 0.25 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.921, 0.969 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 4455, 2766, 2055 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.180, 1.00 |
No. of reflections | 2055 |
No. of parameters | 163 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.64 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure.
S1—O1 | 1.416 (2) | S1—C1 | 1.752 (3) |
S1—O2 | 1.436 (2) | N3—C5 | 1.356 (4) |
S1—N1 | 1.589 (3) | N3—C6 | 1.416 (3) |
O1—S1—O2 | 119.25 (14) | ||
O2—S1—C1—C5 | −36.3 (3) | C5—N3—C6—C11 | 62.2 (5) |
N1—S1—C1—C5 | 78.4 (3) | C6—N3—C5—C4 | 2.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···N2i | 0.88 | 2.12 | 2.890 (4) | 147 |
N1—H102···O1ii | 0.86 | 2.17 | 2.985 (3) | 157 |
N3—H301···O2 | 0.86 | 2.10 | 2.824 (3) | 142 |
N3—H301···O2iii | 0.86 | 2.47 | 3.124 (4) | 134 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z; (iii) −x+1, −y+1, −z. |
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The title compound, (I), is an important intermediate in the preparation of torasemide, which belongs to a group of medications known as the loop diuretics (Rollinger et al., 2002; Wouters et al., 2000). The structure of (I) (Fig. 1) exhibits an elaborate hydrogen-bonding network involving N—H···O dimers and two other hydrogen-bonding motifs (Fig. 2). Selected geometric parameters are listed in Table 1, and the hydrogen-bonding geometry in Table 2. Atom N1 acts as a hydrogen-bond donor to atom O1ii [symmetry code: (ii) −x, −y, −z], so generating a centrosymmetric R22(8) graph-set (Etter, 1990) dimer. Intramolecular hydrogen-bond association from N3—H301 to O2 forms an S(6) graph-set motif. Another hydrogen-bond interaction, N1—H101···N2i [symmetry code: (i) 1 + x, y, z], links molecules into a hydrogen-bonded ribbon motif along the a axis.