4-(3-Methyl­anilino)pyridine-3-sulfonamide

Tang, G.-P.; Gu, J.-M.

doi:10.1107/S1600536805027388

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4-(3-Methylanilino)pyridine-3-sulfonamide

G.-P. Tang and J.-M. Gu

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027388/ob6579sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027388/ob6579Isup2.hkl Contains datablock I

CCDC reference: 287681

checkCIF report

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

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.

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

	Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.
	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

C₁₂H₁₃N₃O₂S	Z = 2
M_r = 263.31	F(000) = 276.00
Triclinic, P1	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	2055 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.085
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.921, T_max = 0.969	k = −11→11
4455 measured reflections	l = −14→14
2766 independent reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.070	w = 4F_o²/[0.004F_o² + 4σ(F_o²) + 0.5]
wR(F²) = 0.180	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.50 e Å⁻³
2055 reflections	Δρ_min = −0.64 e Å⁻³
163 parameters

Crystal data top

C₁₂H₁₃N₃O₂S	γ = 102.911 (12)°
M_r = 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)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2766 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2055 reflections with F² > 2σ(F²)
T_min = 0.921, T_max = 0.969	R_int = 0.085
4455 measured reflections

Refinement top

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	Δρ_max = 0.50 e Å⁻³
2055 reflections	Δρ_min = −0.64 e Å⁻³

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···H123^xii	3.232
O1···N1ⁱ	2.985 (3)	H3···H301^vi	3.347
O2···O2ⁱⁱ	2.902 (3)	H3···H101^vi	3.311
O2···N2ⁱⁱⁱ	3.223 (4)	H4···C9^vii	3.496
O2···N3ⁱⁱ	3.124 (4)	H4···H9^vii	2.608
O2···C2ⁱⁱⁱ	3.451 (4)	H4···H122^v	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···N1^xiii	3.393
N1···N2^iv	2.890 (4)	H7···N1ⁱⁱ	3.039
N1···C2^iv	3.439 (4)	H7···C2ⁱⁱⁱ	3.362
N1···C12^v	3.541 (5)	H7···H2^xiv	3.446
N2···O2ⁱⁱⁱ	3.223 (4)	H7···H2ⁱⁱⁱ	2.648
N2···N1^vi	2.890 (4)	H7···H101^xiii	3.233
N3···O2ⁱⁱ	3.124 (4)	H7···H101ⁱⁱ	3.381
C2···O2ⁱⁱⁱ	3.451 (4)	H7···H102^xiii	3.182
C2···N1^vi	3.439 (4)	H8···N2^xiv	2.711
C3···O2ⁱⁱⁱ	3.161 (4)	H8···C2^xiv	3.166
C4···O2ⁱⁱⁱ	3.392 (4)	H8···C3^xiv	3.294
C6···O2ⁱⁱ	3.438 (4)	H8···C12^vii	3.581
C7···O2ⁱⁱ	3.310 (4)	H8···C12^viii	3.369
C8···C12^vii	3.575 (7)	H8···H2^xiv	3.309
C9···C9^viii	3.349 (6)	H8···H3^xiv	3.511
C9···C10^vii	3.525 (6)	H8···H123^vii	2.827
C10···C9^vii	3.525 (6)	H8···H122^viii	2.912
C12···N1^v	3.541 (5)	H8···H121^viii	3.049
C12···C8^vii	3.575 (7)	H8···H101^xiii	3.154
S1···H7ⁱⁱ	3.288	H9···C4^vii	3.535
S1···H102ⁱ	3.331	H9···C8^viii	3.486
O1···H2ⁱ	3.498	H9···C9^viii	3.016
O1···H7ⁱⁱⁱ	3.403	H9···C10^vii	3.509
O1···H7ⁱⁱ	3.489	H9···C10^viii	3.404
O1···H121^ix	2.849	H9···H4^vii	2.608
O1···H101ⁱ	3.486	H9···H9^viii	2.983
O1···H102ⁱ	2.170	H9···H122^viii	3.585
O2···H3ⁱⁱⁱ	3.512	H11···C11^v	3.463
O2···H7ⁱⁱ	2.943	H11···C12^v	3.478
O2···H301ⁱⁱ	2.468	H11···H3^iv	2.720
N1···H2^iv	3.144	H11···H11^v	2.568
N1···H2ⁱ	2.864	H11···H123^v	3.165
N1···H7^x	3.393	H11···H122^v	3.043
N1···H7ⁱⁱ	3.039	H123···N1^v	3.098
N1···H123^v	3.098	H123···N2^xii	3.331
N1···H121^v	3.314	H123···C7^vii	3.598
N2···H8^xi	2.711	H123···C8^vii	3.032
N2···H123^xii	3.331	H123···C9^vii	3.508
N2···H122^v	3.521	H123···H3^xii	3.232
N2···H301^vi	3.468	H123···H8^vii	2.827
N2···H101^vi	2.115	H123···H11^v	3.165
N2···H102^vi	3.496	H123···H101^v	2.543
N3···H3^iv	3.170	H123···H102^v	2.866
C1···H122^v	3.222	H122···N2^v	3.521
C2···H7ⁱⁱⁱ	3.362	H122···C1^v	3.222
C2···H8^xi	3.166	H122···C2^v	3.420
C2···H122^v	3.420	H122···C3^v	3.321
C2···H301ⁱⁱⁱ	3.385	H122···C4^v	3.125
C2···H101^vi	2.872	H122···C5^v	3.105
C2···H102ⁱ	3.484	H122···C8^viii	3.573
C3···H8^xi	3.294	H122···H4^v	3.561
C3···H122^v	3.321	H122···H8^viii	2.912
C3···H301^vi	3.567	H122···H9^viii	3.585
C3···H101^vi	3.180	H122···H11^v	3.043
C4···H9^vii	3.535	H122···H101^v	3.388
C4···H122^v	3.125	H122···H102^v	3.277
C5···H122^v	3.105	H121···O1^xv	2.849
C6···H3^iv	3.005	H121···N1^v	3.314
C7···H2ⁱⁱⁱ	3.517	H121···C7^vii	3.553
C7···H123^vii	3.598	H121···C8^vii	3.502
C7···H121^vii	3.553	H121···C8^viii	3.386
C8···H9^viii	3.486	H121···H8^viii	3.049
C8···H123^vii	3.032	H121···H101^v	3.141
C8···H122^viii	3.573	H121···H102^v	2.694
C8···H121^vii	3.502	H301···O2ⁱⁱ	2.468
C8···H121^viii	3.386	H301···N2^iv	3.468
C9···H4^vii	3.496	H301···C2ⁱⁱⁱ	3.385
C9···H9^viii	3.016	H301···C3^iv	3.567
C9···H123^vii	3.508	H301···H2ⁱⁱⁱ	3.366
C10···H3^iv	3.539	H301···H3^iv	3.347
C10···H9^vii	3.509	H301···H301ⁱⁱ	3.540
C10···H9^viii	3.404	H101···O1ⁱ	3.486
C11···H3^iv	2.800	H101···N2^iv	2.115
C11···H11^v	3.463	H101···C2^iv	2.872
C12···H8^vii	3.581	H101···C3^iv	3.180
C12···H8^viii	3.369	H101···C12^v	3.177
C12···H11^v	3.478	H101···H2^iv	2.779
C12···H101^v	3.177	H101···H2ⁱ	3.391
C12···H102^v	3.109	H101···H3^iv	3.311
H2···O1ⁱ	3.498	H101···H7^x	3.233
H2···N1^vi	3.144	H101···H7ⁱⁱ	3.381
H2···N1ⁱ	2.864	H101···H8^x	3.154
H2···C7ⁱⁱⁱ	3.517	H101···H123^v	2.543
H2···H7^xi	3.446	H101···H122^v	3.388
H2···H7ⁱⁱⁱ	2.648	H101···H121^v	3.141
H2···H8^xi	3.309	H102···S1ⁱ	3.331
H2···H301ⁱⁱⁱ	3.366	H102···O1ⁱ	2.170
H2···H101^vi	2.779	H102···N2^iv	3.496
H2···H101ⁱ	3.391	H102···C2ⁱ	3.484
H2···H102ⁱ	2.604	H102···C12^v	3.109
H3···O2ⁱⁱⁱ	3.512	H102···H2ⁱ	2.604
H3···N3^vi	3.170	H102···H7^x	3.182
H3···C6^vi	3.005	H102···H123^v	2.866
H3···C10^vi	3.539	H102···H122^v	3.277
H3···C11^vi	2.800	H102···H121^v	2.694
H3···H8^xi	3.511	H102···H102ⁱ	3.168
H3···H11^vi	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···N2^iv	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
M_r	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)
T_min, T_max	0.921, 0.969
No. of measured, independent and observed [F² > 2σ(F²)] reflections	4455, 2766, 2055
R_int	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
Δρ_max, Δρ_min (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.

Selected geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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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