N-{[1-(5-Benzyl­sulfanyl)-1,3,4-oxadiazol-2-yl]eth­yl}-4-chloro­benzene­sulfonamide

The crystal structure of the title compound, C₁₇H₁₆ClN₃O₃S₂, contains hydrogen-bonded chains lying along the b axis. In the molecule, the benzene rings lie almost parallel to each other and the heterocyclic oxadiazole ring is oriented nearly perpendicular to the benzene rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.119
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.03
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

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

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL 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 (Sheldrick, 1997).

N-{[1-(5-benzylthio)-1,3,4-oxadiazol-2-yl]ethyl}chlorobenzenesulfonamide

Crystal data

C17H16ClN3O3S2	F(000) = 848
Mr = 409.90	Dx = 1.488 Mg m^−3
Monoclinic, P21/c	Melting point: 389(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.353 (3) Å	Cell parameters from 11365 reflections
b = 7.592 (3) Å	θ = 3.2–25.3°
c = 23.655 (10) Å	µ = 0.46 mm^−1
β = 100.329 (19)°	T = 173 K
V = 1829.2 (12) Å^3	Needle, colourless
Z = 4	0.25 × 0.06 × 0.03 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3314 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω and φ scans	θmax = 25.3°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.894, Tmax = 0.986	k = −9→9
11365 measured reflections	l = −28→28

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) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 1.95P] where P = (Fo^2 + 2Fc^2)/3
3314 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	0.67113 (9)	0.46812 (14)	0.51049 (4)	0.0513 (3)
S1	0.45091 (8)	0.13902 (12)	0.59500 (3)	0.0377 (2)
S2	0.87213 (8)	0.39808 (12)	0.77432 (3)	0.0359 (2)
O1	0.6294 (2)	0.1217 (3)	0.68979 (9)	0.0363 (5)
O2	0.8491 (2)	0.5587 (3)	0.80306 (10)	0.0497 (7)
O3	1.0009 (2)	0.3254 (4)	0.78179 (10)	0.0470 (6)
N1	0.4765 (2)	−0.0807 (4)	0.68867 (11)	0.0364 (7)
N2	0.5661 (3)	−0.0929 (4)	0.74139 (12)	0.0382 (7)
N3	0.7738 (2)	0.2599 (4)	0.79655 (11)	0.0347 (6)
H3A	0.7183	0.3009	0.8175	0.042*
C1	0.5174 (3)	0.0480 (4)	0.66052 (13)	0.0297 (7)
C2	0.6527 (3)	0.0268 (4)	0.73960 (13)	0.0317 (7)
C3	0.7710 (3)	0.0729 (4)	0.78421 (14)	0.0370 (8)
H3	0.8520	0.0412	0.7690	0.044*
C4	0.7688 (4)	−0.0330 (5)	0.83893 (14)	0.0467 (9)
H4A	0.8480	−0.0070	0.8672	0.056*
H4B	0.7661	−0.1591	0.8299	0.056*
H4C	0.6909	−0.0010	0.8548	0.056*
C5	0.3062 (3)	−0.0004 (5)	0.57737 (14)	0.0380 (8)
H5A	0.3331	−0.1182	0.5703	0.046*
H5B	0.2599	−0.0009	0.6091	0.046*
C6	0.2206 (3)	0.0748 (4)	0.52437 (13)	0.0312 (7)
C7	0.1138 (3)	0.1796 (5)	0.52978 (14)	0.0365 (8)
H7	0.0962	0.2064	0.5673	0.044*
C8	0.0341 (3)	0.2475 (5)	0.48123 (14)	0.0412 (8)
H8	−0.0400	0.3196	0.4851	0.049*
C9	0.0600 (3)	0.2109 (5)	0.42759 (14)	0.0418 (9)
H9	0.0045	0.2572	0.3940	0.050*
C10	0.1658 (3)	0.1065 (5)	0.42175 (14)	0.0419 (8)
H10	0.1847	0.0811	0.3843	0.050*
C11	0.2466 (3)	0.0394 (5)	0.46993 (14)	0.0378 (8)
H11	0.3202	−0.0329	0.4654	0.045*
C12	0.8194 (3)	0.4282 (4)	0.69997 (13)	0.0306 (7)
C13	0.8829 (3)	0.3372 (4)	0.66179 (13)	0.0336 (7)
H13	0.9586	0.2670	0.6764	0.040*
C14	0.8357 (3)	0.3499 (4)	0.60332 (14)	0.0351 (8)
H14	0.8783	0.2871	0.5766	0.042*
C15	0.7267 (3)	0.4525 (5)	0.58404 (13)	0.0357 (8)
C16	0.6627 (3)	0.5434 (4)	0.62153 (15)	0.0387 (8)
H16	0.5874	0.6136	0.6063	0.046*
C17	0.7092 (3)	0.5310 (4)	0.67995 (15)	0.0384 (8)
H17	0.6672	0.5924	0.7072	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0496 (6)	0.0626 (7)	0.0379 (5)	−0.0040 (4)	−0.0025 (4)	0.0097 (4)
S1	0.0337 (4)	0.0453 (5)	0.0325 (4)	−0.0093 (4)	0.0019 (3)	0.0043 (4)
S2	0.0341 (5)	0.0414 (5)	0.0316 (4)	−0.0117 (4)	0.0045 (3)	−0.0034 (4)
O1	0.0321 (12)	0.0385 (14)	0.0356 (12)	−0.0096 (10)	−0.0016 (9)	0.0043 (11)
O2	0.0587 (16)	0.0498 (16)	0.0424 (14)	−0.0093 (13)	0.0142 (12)	−0.0168 (12)
O3	0.0368 (13)	0.0649 (18)	0.0375 (13)	0.0016 (12)	0.0022 (10)	−0.0049 (12)
N1	0.0319 (15)	0.0370 (17)	0.0373 (15)	−0.0062 (12)	−0.0023 (11)	0.0039 (13)
N2	0.0348 (15)	0.0332 (16)	0.0429 (16)	−0.0049 (12)	−0.0027 (12)	0.0067 (13)
N3	0.0341 (15)	0.0367 (16)	0.0349 (14)	−0.0002 (12)	0.0105 (11)	−0.0025 (12)
C1	0.0230 (16)	0.0308 (18)	0.0344 (16)	−0.0026 (13)	0.0030 (12)	−0.0038 (14)
C2	0.0344 (18)	0.0277 (18)	0.0323 (17)	0.0014 (14)	0.0039 (13)	0.0015 (14)
C3	0.0362 (18)	0.0317 (19)	0.0398 (18)	0.0005 (14)	−0.0018 (14)	−0.0010 (15)
C4	0.049 (2)	0.041 (2)	0.044 (2)	−0.0032 (17)	−0.0086 (16)	0.0093 (17)
C5	0.0336 (18)	0.042 (2)	0.0358 (18)	−0.0070 (15)	−0.0012 (13)	0.0018 (16)
C6	0.0336 (17)	0.0294 (18)	0.0289 (16)	−0.0083 (13)	0.0010 (13)	0.0017 (13)
C7	0.0341 (18)	0.043 (2)	0.0322 (17)	−0.0054 (15)	0.0046 (14)	−0.0063 (15)
C8	0.0358 (19)	0.043 (2)	0.0431 (19)	0.0008 (16)	0.0021 (15)	−0.0001 (17)
C9	0.047 (2)	0.040 (2)	0.0340 (18)	−0.0069 (17)	−0.0040 (15)	0.0051 (16)
C10	0.054 (2)	0.043 (2)	0.0294 (17)	−0.0098 (18)	0.0079 (15)	−0.0037 (16)
C11	0.0391 (19)	0.037 (2)	0.0375 (18)	−0.0010 (15)	0.0084 (14)	−0.0050 (16)
C12	0.0312 (17)	0.0302 (18)	0.0310 (16)	−0.0071 (13)	0.0071 (13)	0.0014 (14)
C13	0.0285 (16)	0.0347 (19)	0.0370 (17)	−0.0029 (14)	0.0043 (13)	0.0007 (15)
C14	0.0339 (18)	0.037 (2)	0.0352 (17)	−0.0030 (15)	0.0090 (14)	0.0003 (15)
C15	0.0340 (18)	0.040 (2)	0.0317 (17)	−0.0069 (15)	0.0026 (13)	0.0063 (15)
C16	0.0336 (18)	0.033 (2)	0.048 (2)	0.0035 (15)	0.0056 (15)	0.0077 (16)
C17	0.0398 (19)	0.0302 (19)	0.048 (2)	−0.0001 (15)	0.0154 (15)	−0.0005 (16)

Geometric parameters (Å, º)

Cl1—C15	1.736 (3)	C5—H5B	0.9600
S1—C1	1.723 (3)	C6—C7	1.386 (4)
S1—C5	1.821 (3)	C6—C11	1.388 (4)
S2—O3	1.425 (2)	C7—C8	1.388 (5)
S2—O2	1.437 (3)	C7—H7	0.9601
S2—N3	1.614 (3)	C8—C9	1.371 (5)
S2—C12	1.760 (3)	C8—H8	0.9600
O1—C1	1.360 (3)	C9—C10	1.380 (5)
O1—C2	1.365 (4)	C9—H9	0.9602
N1—C1	1.296 (4)	C10—C11	1.384 (5)
N1—N2	1.418 (4)	C10—H10	0.9599
N2—C2	1.283 (4)	C11—H11	0.9600
N3—C3	1.449 (4)	C12—C13	1.392 (4)
N3—H3A	0.8800	C12—C17	1.393 (5)
C2—C3	1.508 (4)	C13—C14	1.385 (4)
C3—C4	1.527 (5)	C13—H13	0.9600
C3—H3	1.0000	C14—C15	1.380 (5)
C4—H4A	0.9800	C14—H14	0.9600
C4—H4B	0.9800	C15—C16	1.382 (5)
C4—H4C	0.9800	C16—C17	1.383 (5)
C5—C6	1.512 (4)	C16—H16	0.9601
C5—H5A	0.9600	C17—H17	0.9601
C1—S1—C5	98.76 (15)	C7—C6—C11	119.2 (3)
O3—S2—O2	120.08 (15)	C7—C6—C5	119.9 (3)
O3—S2—N3	109.84 (16)	C11—C6—C5	120.9 (3)
O2—S2—N3	103.25 (15)	C6—C7—C8	120.2 (3)
O3—S2—C12	106.85 (14)	C6—C7—H7	119.6
O2—S2—C12	108.33 (16)	C8—C7—H7	120.3
N3—S2—C12	108.00 (14)	C9—C8—C7	120.3 (3)
C1—O1—C2	103.0 (2)	C9—C8—H8	119.8
C1—N1—N2	106.2 (2)	C7—C8—H8	119.9
C2—N2—N1	106.0 (3)	C8—C9—C10	120.0 (3)
C3—N3—S2	124.2 (2)	C8—C9—H9	120.3
C3—N3—H3A	117.9	C10—C9—H9	119.7
S2—N3—H3A	117.9	C9—C10—C11	120.2 (3)
N1—C1—O1	112.1 (3)	C9—C10—H10	120.3
N1—C1—S1	130.5 (2)	C11—C10—H10	119.6
O1—C1—S1	117.4 (2)	C10—C11—C6	120.2 (3)
N2—C2—O1	112.7 (3)	C10—C11—H11	119.5
N2—C2—C3	128.8 (3)	C6—C11—H11	120.2
O1—C2—C3	118.5 (3)	C13—C12—C17	120.7 (3)
N3—C3—C2	110.7 (3)	C13—C12—S2	119.1 (2)
N3—C3—C4	110.4 (3)	C17—C12—S2	120.0 (2)
C2—C3—C4	109.7 (3)	C14—C13—C12	119.4 (3)
N3—C3—H3	108.7	C14—C13—H13	121.2
C2—C3—H3	108.7	C12—C13—H13	119.4
C4—C3—H3	108.7	C15—C14—C13	119.4 (3)
C3—C4—H4A	109.5	C15—C14—H14	120.6
C3—C4—H4B	109.5	C13—C14—H14	120.1
H4A—C4—H4B	109.5	C14—C15—C16	121.8 (3)
C3—C4—H4C	109.5	C14—C15—Cl1	118.3 (3)
H4A—C4—H4C	109.5	C16—C15—Cl1	119.9 (3)
H4B—C4—H4C	109.5	C15—C16—C17	119.1 (3)
C6—C5—S1	107.8 (2)	C15—C16—H16	119.1
C6—C5—H5A	110.6	C17—C16—H16	121.8
S1—C5—H5A	109.2	C16—C17—C12	119.7 (3)
C6—C5—H5B	110.4	C16—C17—H17	121.2
S1—C5—H5B	109.2	C12—C17—H17	119.1
H5A—C5—H5B	109.5
C1—N1—N2—C2	−0.9 (3)	C5—C6—C7—C8	−179.3 (3)
O3—S2—N3—C3	−43.9 (3)	C6—C7—C8—C9	0.3 (5)
O2—S2—N3—C3	−173.1 (3)	C7—C8—C9—C10	−0.1 (5)
C12—S2—N3—C3	72.3 (3)	C8—C9—C10—C11	−0.4 (5)
N2—N1—C1—O1	1.2 (3)	C9—C10—C11—C6	0.8 (5)
N2—N1—C1—S1	−177.0 (2)	C7—C6—C11—C10	−0.7 (5)
C2—O1—C1—N1	−0.9 (3)	C5—C6—C11—C10	178.8 (3)
C2—O1—C1—S1	177.5 (2)	O3—S2—C12—C13	18.6 (3)
C5—S1—C1—N1	0.0 (3)	O2—S2—C12—C13	149.3 (2)
C5—S1—C1—O1	−178.2 (2)	N3—S2—C12—C13	−99.5 (3)
N1—N2—C2—O1	0.4 (4)	O3—S2—C12—C17	−166.3 (3)
N1—N2—C2—C3	180.0 (3)	O2—S2—C12—C17	−35.6 (3)
C1—O1—C2—N2	0.3 (3)	N3—S2—C12—C17	75.5 (3)
C1—O1—C2—C3	−179.4 (3)	C17—C12—C13—C14	0.1 (5)
S2—N3—C3—C2	−105.4 (3)	S2—C12—C13—C14	175.1 (2)
S2—N3—C3—C4	133.0 (3)	C12—C13—C14—C15	0.1 (5)
N2—C2—C3—N3	−128.6 (4)	C13—C14—C15—C16	−0.1 (5)
O1—C2—C3—N3	51.0 (4)	C13—C14—C15—Cl1	179.2 (2)
N2—C2—C3—C4	−6.6 (5)	C14—C15—C16—C17	0.0 (5)
O1—C2—C3—C4	173.0 (3)	Cl1—C15—C16—C17	−179.3 (3)
C1—S1—C5—C6	171.6 (2)	C15—C16—C17—C12	0.2 (5)
S1—C5—C6—C7	−99.0 (3)	C13—C12—C17—C16	−0.2 (5)
S1—C5—C6—C11	81.5 (3)	S2—C12—C17—C16	−175.2 (3)
C11—C6—C7—C8	0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1^i	0.88	2.19	2.936 (4)	143

Symmetry code: (i) −x+1, y+1/2, −z+3/2.