Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C12H13N3O2S, the dihedral angle between the pyridine and benzene rings is 62.1 (1)°. Mol­ecules are linked via N—H...N and N—H...O hydrogen bonds, forming a ribbon motif along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027388/ob6579sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027388/ob6579Isup2.hkl
Contains datablock I

CCDC reference: 287681

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Comment top

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.

Experimental top

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.

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram for (I), showing the hydrogen-bonded (dashed lines) motif. [Symmetry codes: (i) 1 + x, y, z; (ii) −x, −y, −z.]
4-(3-Methylanilino)pyridine-3-sulfonamide top
Crystal data top
C12H13N3O2SZ = 2
Mr = 263.31F(000) = 276.00
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.714 (3) ÅCell parameters from 5401 reflections
b = 8.630 (4) Åθ = 2.5–27.5°
c = 11.403 (4) ŵ = 0.26 mm1
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
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2055 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.085
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.921, Tmax = 0.969k = 1111
4455 measured reflectionsl = 1414
2766 independent reflections
Refinement top
Refinement on F2H 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 = 1.00Δρmax = 0.50 e Å3
2055 reflectionsΔρmin = 0.64 e Å3
163 parameters
Crystal data top
C12H13N3O2Sγ = 102.911 (12)°
Mr = 263.31V = 614.7 (4) Å3
Triclinic, P1Z = 2
a = 6.714 (3) ÅMo Kα radiation
b = 8.630 (4) ŵ = 0.26 mm1
c = 11.403 (4) ÅT = 296 K
α = 98.640 (11)°0.30 × 0.25 × 0.12 mm
β = 102.57 (2)°
Data collection top
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 = 0.969Rint = 0.085
4455 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.070163 parameters
wR(F2) = 0.180H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.50 e Å3
2055 reflectionsΔρmin = 0.64 e Å3
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.16127 (12)0.25485 (9)0.00281 (6)0.0326 (2)
O10.0069 (4)0.1381 (2)0.0917 (2)0.0457 (6)
O20.2973 (4)0.3788 (2)0.0420 (2)0.0397 (6)
N10.3091 (5)0.1586 (3)0.0665 (2)0.0403 (7)
N20.2537 (4)0.3297 (3)0.1840 (2)0.0432 (8)
N30.3634 (5)0.5754 (3)0.1919 (2)0.0430 (7)
C10.0518 (5)0.3516 (3)0.1037 (2)0.0310 (7)
C20.1524 (5)0.2773 (4)0.1052 (3)0.0372 (8)
C30.1419 (6)0.4649 (4)0.2668 (3)0.0456 (10)
C40.0602 (5)0.5494 (4)0.2734 (3)0.0424 (9)
C50.1632 (5)0.4954 (3)0.1886 (2)0.0345 (8)
C60.4878 (5)0.7142 (4)0.2824 (2)0.0355 (8)
C70.5637 (6)0.8578 (4)0.2487 (3)0.0446 (9)
C80.6917 (7)0.9897 (4)0.3376 (4)0.0528 (11)
C90.7386 (7)0.9779 (4)0.4582 (3)0.0519 (10)
C100.6606 (6)0.8343 (4)0.4936 (3)0.0455 (9)
C110.5419 (5)0.7029 (4)0.4042 (3)0.0404 (9)
C120.7181 (8)0.8196 (6)0.6250 (3)0.0662 (13)
H20.22830.17800.04320.044*
H30.21020.50670.32770.056*
H40.13110.64820.33670.049*
H70.52750.86580.16220.051*
H80.75021.09150.31410.059*
H90.82631.07350.52090.056*
H110.49000.59900.42680.049*
H1210.79710.92390.67550.076*
H1220.80200.74340.63430.076*
H1230.59070.78230.64960.076*
H1010.42060.20600.12790.048*
H1020.22260.09100.09290.047*
H3010.38520.55670.12000.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0304 (4)0.0320 (4)0.0291 (4)0.0032 (3)0.0088 (3)0.0028 (2)
O10.0438 (15)0.0454 (13)0.0349 (11)0.0067 (12)0.0095 (11)0.0013 (10)
O20.0382 (13)0.0394 (12)0.0365 (11)0.0042 (10)0.0145 (10)0.0071 (9)
N10.0386 (17)0.0380 (14)0.0415 (14)0.0038 (12)0.0129 (13)0.0056 (11)
N20.0286 (15)0.0486 (16)0.0541 (17)0.0092 (13)0.0137 (13)0.0132 (13)
N30.0370 (16)0.0442 (15)0.0383 (14)0.0025 (13)0.0133 (13)0.0052 (12)
C10.0280 (16)0.0332 (15)0.0330 (14)0.0094 (13)0.0074 (12)0.0096 (12)
C20.0256 (16)0.0399 (16)0.0441 (17)0.0047 (14)0.0077 (14)0.0109 (14)
C30.039 (2)0.051 (2)0.051 (2)0.0155 (17)0.0183 (16)0.0059 (16)
C40.038 (2)0.0406 (17)0.0443 (18)0.0100 (15)0.0082 (15)0.0004 (14)
C50.0334 (17)0.0328 (15)0.0363 (15)0.0076 (13)0.0091 (13)0.0059 (12)
C60.0272 (16)0.0380 (16)0.0355 (15)0.0056 (13)0.0050 (13)0.0010 (12)
C70.043 (2)0.0440 (18)0.0411 (17)0.0063 (16)0.0063 (16)0.0071 (14)
C80.047 (2)0.0367 (18)0.065 (2)0.0001 (17)0.0073 (19)0.0083 (17)
C90.048 (2)0.0392 (18)0.052 (2)0.0006 (17)0.0045 (18)0.0110 (15)
C100.043 (2)0.049 (2)0.0404 (17)0.0129 (17)0.0080 (16)0.0007 (15)
C110.0397 (19)0.0380 (17)0.0435 (17)0.0102 (15)0.0119 (15)0.0069 (14)
C120.059 (2)0.086 (3)0.044 (2)0.021 (2)0.001 (2)0.002 (2)
Geometric parameters (Å, º) top
S1—O11.416 (2)C9—C101.388 (5)
S1—O21.436 (2)C10—C111.363 (4)
S1—N11.589 (3)C10—C121.495 (5)
S1—C11.752 (3)N1—H1010.875
N2—C21.325 (5)N1—H1020.863
N2—C31.336 (4)N3—H3010.861
N3—C51.356 (4)C2—H20.980
N3—C61.416 (3)C3—H30.980
C1—C21.382 (4)C4—H40.980
C1—C51.395 (3)C7—H70.980
C3—C41.369 (5)C8—H80.980
C4—C51.389 (5)C9—H90.980
C6—C71.374 (5)C11—H110.980
C6—C111.381 (4)C12—H1230.960
C7—C81.378 (4)C12—H1220.960
C8—C91.367 (6)C12—H1210.960
O1···O1i3.403 (3)H3···H123xii3.232
O1···N1i2.985 (3)H3···H301vi3.347
O2···O2ii2.902 (3)H3···H101vi3.311
O2···N2iii3.223 (4)H4···C9vii3.496
O2···N3ii3.124 (4)H4···H9vii2.608
O2···C2iii3.451 (4)H4···H122v3.561
O2···C3iii3.161 (4)H7···S1ii3.288
O2···C4iii3.392 (4)H7···O1iii3.403
O2···C6ii3.438 (4)H7···O1ii3.489
O2···C7ii3.310 (4)H7···O2ii2.943
N1···O1i2.985 (3)H7···N1xiii3.393
N1···N2iv2.890 (4)H7···N1ii3.039
N1···C2iv3.439 (4)H7···C2iii3.362
N1···C12v3.541 (5)H7···H2xiv3.446
N2···O2iii3.223 (4)H7···H2iii2.648
N2···N1vi2.890 (4)H7···H101xiii3.233
N3···O2ii3.124 (4)H7···H101ii3.381
C2···O2iii3.451 (4)H7···H102xiii3.182
C2···N1vi3.439 (4)H8···N2xiv2.711
C3···O2iii3.161 (4)H8···C2xiv3.166
C4···O2iii3.392 (4)H8···C3xiv3.294
C6···O2ii3.438 (4)H8···C12vii3.581
C7···O2ii3.310 (4)H8···C12viii3.369
C8···C12vii3.575 (7)H8···H2xiv3.309
C9···C9viii3.349 (6)H8···H3xiv3.511
C9···C10vii3.525 (6)H8···H123vii2.827
C10···C9vii3.525 (6)H8···H122viii2.912
C12···N1v3.541 (5)H8···H121viii3.049
C12···C8vii3.575 (7)H8···H101xiii3.154
S1···H7ii3.288H9···C4vii3.535
S1···H102i3.331H9···C8viii3.486
O1···H2i3.498H9···C9viii3.016
O1···H7iii3.403H9···C10vii3.509
O1···H7ii3.489H9···C10viii3.404
O1···H121ix2.849H9···H4vii2.608
O1···H101i3.486H9···H9viii2.983
O1···H102i2.170H9···H122viii3.585
O2···H3iii3.512H11···C11v3.463
O2···H7ii2.943H11···C12v3.478
O2···H301ii2.468H11···H3iv2.720
N1···H2iv3.144H11···H11v2.568
N1···H2i2.864H11···H123v3.165
N1···H7x3.393H11···H122v3.043
N1···H7ii3.039H123···N1v3.098
N1···H123v3.098H123···N2xii3.331
N1···H121v3.314H123···C7vii3.598
N2···H8xi2.711H123···C8vii3.032
N2···H123xii3.331H123···C9vii3.508
N2···H122v3.521H123···H3xii3.232
N2···H301vi3.468H123···H8vii2.827
N2···H101vi2.115H123···H11v3.165
N2···H102vi3.496H123···H101v2.543
N3···H3iv3.170H123···H102v2.866
C1···H122v3.222H122···N2v3.521
C2···H7iii3.362H122···C1v3.222
C2···H8xi3.166H122···C2v3.420
C2···H122v3.420H122···C3v3.321
C2···H301iii3.385H122···C4v3.125
C2···H101vi2.872H122···C5v3.105
C2···H102i3.484H122···C8viii3.573
C3···H8xi3.294H122···H4v3.561
C3···H122v3.321H122···H8viii2.912
C3···H301vi3.567H122···H9viii3.585
C3···H101vi3.180H122···H11v3.043
C4···H9vii3.535H122···H101v3.388
C4···H122v3.125H122···H102v3.277
C5···H122v3.105H121···O1xv2.849
C6···H3iv3.005H121···N1v3.314
C7···H2iii3.517H121···C7vii3.553
C7···H123vii3.598H121···C8vii3.502
C7···H121vii3.553H121···C8viii3.386
C8···H9viii3.486H121···H8viii3.049
C8···H123vii3.032H121···H101v3.141
C8···H122viii3.573H121···H102v2.694
C8···H121vii3.502H301···O2ii2.468
C8···H121viii3.386H301···N2iv3.468
C9···H4vii3.496H301···C2iii3.385
C9···H9viii3.016H301···C3iv3.567
C9···H123vii3.508H301···H2iii3.366
C10···H3iv3.539H301···H3iv3.347
C10···H9vii3.509H301···H301ii3.540
C10···H9viii3.404H101···O1i3.486
C11···H3iv2.800H101···N2iv2.115
C11···H11v3.463H101···C2iv2.872
C12···H8vii3.581H101···C3iv3.180
C12···H8viii3.369H101···C12v3.177
C12···H11v3.478H101···H2iv2.779
C12···H101v3.177H101···H2i3.391
C12···H102v3.109H101···H3iv3.311
H2···O1i3.498H101···H7x3.233
H2···N1vi3.144H101···H7ii3.381
H2···N1i2.864H101···H8x3.154
H2···C7iii3.517H101···H123v2.543
H2···H7xi3.446H101···H122v3.388
H2···H7iii2.648H101···H121v3.141
H2···H8xi3.309H102···S1i3.331
H2···H301iii3.366H102···O1i2.170
H2···H101vi2.779H102···N2iv3.496
H2···H101i3.391H102···C2i3.484
H2···H102i2.604H102···C12v3.109
H3···O2iii3.512H102···H2i2.604
H3···N3vi3.170H102···H7x3.182
H3···C6vi3.005H102···H123v2.866
H3···C10vi3.539H102···H122v3.277
H3···C11vi2.800H102···H121v2.694
H3···H8xi3.511H102···H102i3.168
H3···H11vi2.720
O1—S1—O2119.25 (14)C6—C11—C10121.3 (3)
O1—S1—N1107.19 (15)S1—N1—H101123.3
O1—S1—C1107.60 (16)S1—N1—H102103.0
O2—S1—N1106.45 (16)H101—N1—H102107.8
O2—S1—C1107.76 (14)C5—N3—H301110.3
N1—S1—C1108.17 (16)C6—N3—H301121.5
C2—N2—C3114.7 (3)N2—C2—H2117.3
C5—N3—C6124.1 (3)C1—C2—H2117.5
S1—C1—C2117.6 (2)N2—C3—H3117.2
S1—C1—C5123.1 (2)C4—C3—H3117.5
C2—C1—C5119.2 (3)C3—C4—H4120.2
N2—C2—C1125.1 (2)C5—C4—H4120.1
N2—C3—C4125.3 (4)C6—C7—H7120.2
C3—C4—C5119.6 (2)C8—C7—H7120.5
N3—C5—C1122.4 (3)C7—C8—H8119.8
N3—C5—C4121.6 (2)C9—C8—H8120.2
C1—C5—C4116.0 (3)C8—C9—H9119.3
N3—C6—C7120.2 (2)C10—C9—H9119.5
N3—C6—C11119.8 (3)C6—C11—H11119.2
C7—C6—C11119.9 (2)C10—C11—H11119.5
C6—C7—C8119.3 (3)C10—C12—H123109.0
C7—C8—C9120.0 (3)C10—C12—H122110.0
C8—C9—C10121.2 (3)C10—C12—H121109.4
C9—C10—C11118.1 (3)H123—C12—H122109.5
C9—C10—C12121.2 (3)H123—C12—H121109.5
C11—C10—C12120.6 (3)H122—C12—H121109.5
O1—S1—C1—C216.2 (3)C2—C1—C5—C42.8 (5)
O1—S1—C1—C5166.1 (2)C5—C1—C2—N21.6 (5)
O2—S1—C1—C2146.0 (2)N2—C3—C4—C50.4 (6)
O2—S1—C1—C536.3 (3)C3—C4—C5—N3179.9 (2)
N1—S1—C1—C299.3 (2)C3—C4—C5—C12.3 (5)
N1—S1—C1—C578.4 (3)N3—C6—C7—C8177.3 (4)
C2—N2—C3—C41.0 (6)N3—C6—C11—C10179.7 (4)
C3—N2—C2—C10.4 (5)C7—C6—C11—C103.6 (6)
C5—N3—C6—C7121.2 (4)C11—C6—C7—C80.7 (6)
C5—N3—C6—C1162.2 (5)C6—C7—C8—C91.3 (7)
C6—N3—C5—C1174.8 (3)C7—C8—C9—C100.5 (7)
C6—N3—C5—C42.6 (5)C8—C9—C10—C112.4 (7)
S1—C1—C2—N2176.2 (3)C8—C9—C10—C12177.8 (4)
S1—C1—C5—N32.8 (5)C9—C10—C11—C64.4 (6)
S1—C1—C5—C4174.8 (2)C12—C10—C11—C6179.9 (3)
C2—C1—C5—N3179.6 (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) x1, y, z; (vii) x+1, y+2, z+1; (viii) x+2, y+2, z+1; (ix) x1, y1, z1; (x) x, y1, z; (xi) x1, y1, 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.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···N2iv0.882.122.890 (4)147
N1—H102···O1i0.862.172.985 (3)157
N3—H301···O20.862.102.824 (3)142
N3—H301···O2ii0.862.473.124 (4)134
Symmetry codes: (i) x, y, z; (ii) x+1, y+1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC12H13N3O2S
Mr263.31
Crystal system, space groupTriclinic, 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)
V3)614.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.30 × 0.25 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.921, 0.969
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
4455, 2766, 2055
Rint0.085
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.180, 1.00
No. of reflections2055
No. of parameters163
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Selected geometric parameters (Å, º) top
S1—O11.416 (2)S1—C11.752 (3)
S1—O21.436 (2)N3—C51.356 (4)
S1—N11.589 (3)N3—C61.416 (3)
O1—S1—O2119.25 (14)
O2—S1—C1—C536.3 (3)C5—N3—C6—C1162.2 (5)
N1—S1—C1—C578.4 (3)C6—N3—C5—C42.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···N2i0.882.122.890 (4)147
N1—H102···O1ii0.862.172.985 (3)157
N3—H301···O20.862.102.824 (3)142
N3—H301···O2iii0.862.473.124 (4)134
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x+1, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds