4-Methyl-N-[1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-­yl)prop­yl]benzene­sulfonamide

The structure of the title compound, C₁₂H₁₅N₃O₂S₂, incorporating oxadiazole and sulfonamide units, contains two conformers in different proportions. The heterocyclic five-membered ring is inclined at 17.6 (1)° with respect to the benzene ring. The structure is stabilized by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.117
• Data-to-parameter ratio = 21.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O3'    ..  O3'     ..       2.83 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        C3'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      10.10 Deg.
              S2'  -C6   -S2      1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-Methyl-N-[1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2- yl)propyl]benzenesulfonamide

Crystal data

C12H15N3O3S2	F(000) = 1312
Mr = 313.39	Dx = 1.425 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5916 reflections
a = 14.098 (5) Å	θ = 3.2–30.0°
b = 16.575 (8) Å	µ = 0.37 mm^−1
c = 13.695 (5) Å	T = 173 K
β = 114.05 (2)°	Block, colorless
V = 2922 (2) Å^3	0.18 × 0.16 × 0.14 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	4257 independent reflections
Radiation source: fine-focus sealed tube	3265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω and φ scans	θmax = 30.0°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −19→19
Tmin = 0.936, Tmax = 0.950	k = −23→15
5916 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 4.48P] where P = (Fo^2 + 2Fc^2)/3
4257 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.53 e Å^−3
4 restraints	Δρmin = −0.54 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.55151 (5)	0.44288 (3)	0.12394 (4)	0.04341 (16)
O1	0.68687 (10)	0.42991 (8)	0.32887 (10)	0.0297 (3)
S2	0.98905 (6)	0.35917 (4)	0.51816 (5)	0.02780 (16)	0.898 (2)
O2	1.01417 (13)	0.30440 (10)	0.60736 (12)	0.0359 (4)	0.898 (2)
O3	1.06947 (14)	0.41251 (10)	0.51767 (16)	0.0380 (4)	0.898 (2)
S2'	0.9946 (6)	0.3427 (4)	0.5300 (3)	0.02780 (16)	0.102 (2)
O2'	1.0629 (11)	0.2815 (7)	0.5962 (11)	0.0359 (4)	0.102 (2)
O3'	1.0267 (12)	0.4178 (7)	0.5002 (15)	0.0380 (4)	0.102 (2)
N1	0.61995 (12)	0.31653 (10)	0.25982 (12)	0.0289 (3)
H1	0.5828	0.2796	0.2141	0.035*
N2	0.68669 (12)	0.29961 (10)	0.36459 (12)	0.0308 (3)
N3	0.89695 (12)	0.41784 (10)	0.51639 (14)	0.0272 (4)	0.898 (2)
H3	0.9059	0.4704	0.5170	0.033*	0.898 (2)
C3	0.79995 (14)	0.38655 (12)	0.51386 (15)	0.0310 (4)
H3A	0.8158	0.3344	0.5540	0.037*	0.898 (2)
N3'	0.8897 (8)	0.3515 (9)	0.5490 (12)	0.0272 (4)	0.102 (2)
H3'	0.8955	0.3210	0.6039	0.033*	0.102 (2)
C3'	0.79995 (14)	0.38655 (12)	0.51386 (15)	0.0310 (4)	0.00
H3'1	0.8281	0.4333	0.4880	0.037*	0.102 (2)
C1	0.61794 (14)	0.39442 (12)	0.23564 (14)	0.0289 (4)
C2	0.72397 (14)	0.36881 (11)	0.40198 (14)	0.0274 (4)
C4	0.75528 (15)	0.44336 (12)	0.57119 (15)	0.0314 (4)
H4A	0.7487	0.4980	0.5398	0.038*
H4B	0.6848	0.4248	0.5599	0.038*
C5	0.82184 (19)	0.44806 (17)	0.69008 (18)	0.0522 (6)
H5A	0.7882	0.4831	0.7241	0.063*
H5B	0.8901	0.4702	0.7019	0.063*
H5C	0.8303	0.3939	0.7212	0.063*
C6	0.94094 (14)	0.30011 (12)	0.40061 (15)	0.0297 (4)
C7	0.90145 (16)	0.34027 (13)	0.30256 (17)	0.0365 (4)
H7	0.9019	0.3975	0.2999	0.044*
C8	0.86155 (17)	0.29546 (15)	0.20917 (17)	0.0419 (5)
H8	0.8337	0.3225	0.1422	0.050*
C9	0.86159 (16)	0.21148 (15)	0.21175 (18)	0.0407 (5)
C10	0.90142 (17)	0.17321 (14)	0.31084 (19)	0.0404 (5)
H10	0.9019	0.1159	0.3138	0.048*
C11	0.94046 (15)	0.21708 (12)	0.40547 (17)	0.0345 (4)
H11	0.9665	0.1902	0.4726	0.041*
C12	0.8198 (2)	0.16219 (19)	0.1102 (2)	0.0587 (7)
H12A	0.8538	0.1093	0.1237	0.070*
H12B	0.8337	0.1903	0.0545	0.070*
H12C	0.7447	0.1550	0.0866	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0523 (3)	0.0342 (3)	0.0295 (2)	−0.0070 (2)	0.0021 (2)	0.0067 (2)
O1	0.0288 (6)	0.0246 (6)	0.0297 (6)	−0.0057 (5)	0.0056 (5)	−0.0011 (5)
S2	0.0207 (2)	0.0248 (3)	0.0316 (3)	0.0032 (3)	0.00431 (19)	0.0081 (2)
O2	0.0377 (9)	0.0263 (8)	0.0321 (8)	0.0056 (7)	0.0022 (7)	0.0076 (6)
O3	0.0232 (8)	0.0277 (8)	0.0584 (11)	−0.0015 (7)	0.0117 (8)	0.0020 (7)
S2'	0.0207 (2)	0.0248 (3)	0.0316 (3)	0.0032 (3)	0.00431 (19)	0.0081 (2)
O2'	0.0377 (9)	0.0263 (8)	0.0321 (8)	0.0056 (7)	0.0022 (7)	0.0076 (6)
O3'	0.0232 (8)	0.0277 (8)	0.0584 (11)	−0.0015 (7)	0.0117 (8)	0.0020 (7)
N1	0.0276 (7)	0.0258 (8)	0.0264 (7)	−0.0037 (6)	0.0039 (6)	−0.0016 (6)
N2	0.0311 (8)	0.0264 (8)	0.0277 (7)	−0.0001 (6)	0.0048 (6)	0.0000 (6)
N3	0.0224 (7)	0.0184 (7)	0.0373 (9)	−0.0013 (6)	0.0086 (7)	0.0012 (6)
C3	0.0258 (8)	0.0307 (9)	0.0301 (9)	0.0016 (7)	0.0049 (7)	−0.0028 (7)
N3'	0.0224 (7)	0.0184 (7)	0.0373 (9)	−0.0013 (6)	0.0086 (7)	0.0012 (6)
C3'	0.0258 (8)	0.0307 (9)	0.0301 (9)	0.0016 (7)	0.0049 (7)	−0.0028 (7)
C1	0.0264 (8)	0.0283 (9)	0.0290 (9)	−0.0058 (7)	0.0082 (7)	−0.0016 (7)
C2	0.0235 (8)	0.0258 (9)	0.0300 (8)	0.0012 (7)	0.0079 (7)	0.0000 (7)
C4	0.0281 (9)	0.0330 (10)	0.0313 (9)	0.0007 (8)	0.0102 (7)	−0.0022 (8)
C5	0.0434 (12)	0.0637 (16)	0.0385 (12)	0.0074 (11)	0.0054 (10)	−0.0196 (11)
C6	0.0239 (8)	0.0305 (10)	0.0337 (9)	0.0017 (7)	0.0109 (7)	0.0052 (7)
C7	0.0368 (10)	0.0338 (10)	0.0375 (10)	0.0035 (8)	0.0136 (8)	0.0094 (8)
C8	0.0365 (11)	0.0523 (14)	0.0334 (10)	0.0013 (10)	0.0107 (9)	0.0073 (9)
C9	0.0274 (9)	0.0513 (13)	0.0423 (11)	−0.0073 (9)	0.0130 (8)	−0.0059 (10)
C10	0.0383 (11)	0.0325 (11)	0.0511 (12)	−0.0055 (9)	0.0191 (10)	−0.0020 (9)
C11	0.0325 (9)	0.0304 (10)	0.0399 (10)	0.0011 (8)	0.0140 (8)	0.0080 (8)
C12	0.0448 (13)	0.0734 (19)	0.0534 (15)	−0.0158 (13)	0.0155 (12)	−0.0210 (13)

Geometric parameters (Å, º)

S1—C1	1.642 (2)	C4—C5	1.514 (3)
O1—C2	1.369 (2)	C4—H4A	0.9900
O1—C1	1.382 (2)	C4—H4B	0.9900
S2—O3	1.440 (2)	C5—H5A	0.9800
S2—O2	1.445 (2)	C5—H5B	0.9800
S2—N3	1.615 (2)	C5—H5C	0.9800
S2—C6	1.766 (2)	C6—C11	1.378 (3)
S2'—O2'	1.439 (2)	C6—C7	1.395 (3)
S2'—O3'	1.440 (2)	C7—C8	1.385 (3)
S2'—N3'	1.610 (2)	C7—H7	0.9500
S2'—C6	1.766 (2)	C8—C9	1.392 (3)
N1—C1	1.330 (2)	C8—H8	0.9500
N1—N2	1.387 (2)	C9—C10	1.392 (3)
N1—H1	0.8800	C9—C12	1.510 (3)
N2—C2	1.279 (2)	C10—C11	1.389 (3)
N3—C3	1.450 (3)	C10—H10	0.9500
N3—H3	0.8800	C11—H11	0.9500
C3—C2	1.498 (2)	C12—H12A	0.9800
C3—C4	1.517 (3)	C12—H12B	0.9800
C3—H3A	1.0000	C12—H12C	0.9800
N3'—H3'	0.8800
C2—O1—C1	106.02 (14)	C5—C4—H4B	109.1
O3—S2—O2	117.87 (11)	C3—C4—H4B	109.1
O3—S2—N3	105.07 (11)	H4A—C4—H4B	107.8
O2—S2—N3	108.03 (11)	C4—C5—H5A	109.5
O3—S2—C6	110.29 (11)	C4—C5—H5B	109.5
O2—S2—C6	107.04 (10)	H5A—C5—H5B	109.5
N3—S2—C6	108.20 (10)	C4—C5—H5C	109.5
O2'—S2'—O3'	125.6 (11)	H5A—C5—H5C	109.5
O2'—S2'—N3'	112.6 (10)	H5B—C5—H5C	109.5
O3'—S2'—N3'	112.6 (10)	C11—C6—C7	121.00 (19)
O2'—S2'—C6	104.6 (7)	C11—C6—S2'	111.1 (3)
O3'—S2'—C6	96.7 (9)	C7—C6—S2'	127.9 (3)
N3'—S2'—C6	98.8 (7)	C11—C6—S2	121.14 (15)
C1—N1—N2	112.98 (15)	C7—C6—S2	117.85 (16)
C1—N1—H1	123.5	S2'—C6—S2	10.1 (3)
N2—N1—H1	123.5	C8—C7—C6	119.0 (2)
C2—N2—N1	103.17 (15)	C8—C7—H7	120.5
C3—N3—S2	122.00 (14)	C6—C7—H7	120.5
C3—N3—H3	119.0	C7—C8—C9	121.1 (2)
S2—N3—H3	119.0	C7—C8—H8	119.4
N3—C3—C2	111.65 (16)	C9—C8—H8	119.4
N3—C3—C4	110.61 (16)	C10—C9—C8	118.4 (2)
C2—C3—C4	112.12 (15)	C10—C9—C12	120.1 (2)
N3—C3—H3A	107.4	C8—C9—C12	121.4 (2)
C2—C3—H3A	107.4	C11—C10—C9	121.3 (2)
C4—C3—H3A	107.4	C11—C10—H10	119.3
S2'—N3'—H3'	108.3	C9—C10—H10	119.3
N1—C1—O1	104.34 (15)	C6—C11—C10	119.05 (19)
N1—C1—S1	130.77 (14)	C6—C11—H11	120.5
O1—C1—S1	124.89 (14)	C10—C11—H11	120.5
N2—C2—O1	113.49 (16)	C9—C12—H12A	109.5
N2—C2—C3	126.27 (17)	C9—C12—H12B	109.5
O1—C2—C3	120.24 (16)	H12A—C12—H12B	109.5
C5—C4—C3	112.47 (17)	C9—C12—H12C	109.5
C5—C4—H4A	109.1	H12A—C12—H12C	109.5
C3—C4—H4A	109.1	H12B—C12—H12C	109.5
C1—N1—N2—C2	0.1 (2)	N3'—S2'—C6—C7	89.0 (7)
O3—S2—N3—C3	178.56 (16)	O2'—S2'—C6—S2	−157 (2)
O2—S2—N3—C3	−54.81 (17)	O3'—S2'—C6—S2	−27.6 (16)
C6—S2—N3—C3	60.74 (18)	N3'—S2'—C6—S2	86.6 (19)
S2—N3—C3—C2	−85.42 (19)	O3—S2—C6—C11	124.39 (18)
S2—N3—C3—C4	148.98 (14)	O2—S2—C6—C11	−5.0 (2)
N2—N1—C1—O1	0.2 (2)	N3—S2—C6—C11	−121.19 (17)
N2—N1—C1—S1	−179.52 (15)	O3—S2—C6—C7	−56.87 (19)
C2—O1—C1—N1	−0.4 (2)	O2—S2—C6—C7	173.75 (16)
C2—O1—C1—S1	179.33 (15)	N3—S2—C6—C7	57.55 (18)
N1—N2—C2—O1	−0.4 (2)	O3—S2—C6—S2'	121.0 (19)
N1—N2—C2—C3	178.92 (18)	O2—S2—C6—S2'	−8.4 (18)
C1—O1—C2—N2	0.5 (2)	N3—S2—C6—S2'	−124.6 (19)
C1—O1—C2—C3	−178.81 (16)	C11—C6—C7—C8	−0.1 (3)
N3—C3—C2—N2	117.2 (2)	S2'—C6—C7—C8	−179.4 (4)
C4—C3—C2—N2	−118.1 (2)	S2—C6—C7—C8	−178.88 (17)
N3—C3—C2—O1	−63.6 (2)	C6—C7—C8—C9	−0.9 (3)
C4—C3—C2—O1	61.2 (2)	C7—C8—C9—C10	0.9 (3)
N3—C3—C4—C5	−66.6 (2)	C7—C8—C9—C12	−179.0 (2)
C2—C3—C4—C5	168.09 (19)	C8—C9—C10—C11	0.0 (3)
O2'—S2'—C6—C11	26.0 (9)	C12—C9—C10—C11	179.9 (2)
O3'—S2'—C6—C11	155.5 (8)	C7—C6—C11—C10	1.0 (3)
N3'—S2'—C6—C11	−90.3 (6)	S2'—C6—C11—C10	−179.6 (4)
O2'—S2'—C6—C7	−154.7 (8)	S2—C6—C11—C10	179.73 (16)
O3'—S2'—C6—C7	−25.2 (9)	C9—C10—C11—C6	−1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	1.96	2.840 (2)	173
N1—H1···O2′^i	0.88	1.83	2.615 (10)	148
N3—H3···O3^ii	0.88	2.06	2.920 (3)	165
N3′—H3′···N2^iii	0.88	2.44	3.141 (14)	137

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, −y+1/2, −z+1.