Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

Within a research project aimed at the design of new sweeteners, the tetrazole moiety was introduced to arylsulfonylalkanoic acids (ASA) as a bioisostere of the carboxyl group. The crystal structures of four newly synthesized tetrazole derivatives and one intermediate product of the reaction were determined in order to explain the bitter taste of these compounds. Three chiral compounds crystallize as racemic mixtures in centrosymmetric space groups of the monoclinic system, whereas the non-chiral compound, with a higher dipole moment, crystallizes in the polar space group Cc. Intermolecular N—H...N hydrogen bonds between tetrazole moieties were observed in all four structures and are compared with the analogous interactions observed in tetrazole derivatives deposited in the Cambridge Structural Database (CSD). Specifically, the typical N1—H...N4 as well as N1—H...N3 interactions, which are less abundant in the CSD, are described. The formation of the latter interaction type can be hypothetically explained by an asymmetry of π-electron distribution in the tetrazole rings caused by the crystalline environment. Important features of the crystal architecture are the chains of molecules linked by N—H...N bonds. A possible reason for the lack of a sweet taste of the tetrazoles investigated may be the improper position of the tetrazole H atom, and the mutual orientation of the proton donor and acceptor in their molecules. This orientation does not allow the tetrazoles to interact with the sweet-taste receptor in a way similar to that of ASA. The bitter taste of the investigated compounds needs further study.

Computing details

Data collection: Collect (Nonius BV, 1997-2000) for (1), (2), (3). Cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997) for (1), (2), (3). Data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 19) for (1); HKL DENZO and SCALEPACK (Otwinowski & Minor 19 for (2); HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) for (3). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (1), (2), (2a). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for (1), (2), (2a). Software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) for (1), (2), (2a).

(1) 5-[1-(4-methylphenylsulfonyl)propyl]-1H-tetrazol

Crystal data

C11H14N4O2S	F(000) = 560
Mr = 266.32	Dx = 1.36 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P2ybc	Cell parameters from 5481 reflections
a = 10.9886 (3) Å	θ = 1–27.5°
b = 12.6952 (5) Å	µ = 0.25 mm^−1
c = 9.6299 (2) Å	T = 293 K
β = 104.535 (2)°	Block, white
V = 1300.40 (7) Å^3	0.35 × 0.15 × 0.13 mm
Z = 4

Data collection

KappaCCD diffractometer	2338 reflections with I > 2σ(I)
CCD scans	Rint = 0.033
Absorption correction: multi-scan HKL Denzo and Scalepack (Otwinowski & Minor 1997)	θmax = 27.4°, θmin = 3.9°
Tmin = 0.92, Tmax = 0.97	h = −14→13
15274 measured reflections	k = −15→16
2939 independent reflections	l = 0→12

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.4433P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max < 0.001
wR(F^2) = 0.124	Δρmax = 0.27 e Å^−3
S = 1.08	Δρmin = −0.37 e Å^−3
2939 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
168 parameters	Extinction coefficient: 0.034 (4)
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.18650 (5)	0.05048 (4)	0.36070 (5)	0.04430 (19)
N2	0.17355 (18)	−0.27513 (13)	0.17119 (16)	0.0436 (4)
O1	0.24437 (17)	−0.02346 (14)	0.46991 (15)	0.0613 (5)
O2	0.13319 (17)	0.14563 (12)	0.40064 (17)	0.0615 (5)
N3	0.14836 (17)	−0.23347 (13)	0.04469 (15)	0.0431 (4)
N1	0.14603 (16)	−0.20053 (12)	0.25747 (15)	0.0384 (4)
H1N	0.158 (2)	−0.2146 (17)	0.354 (2)	0.046*
N4	0.10555 (17)	−0.13348 (13)	0.04631 (15)	0.0419 (4)
C7	0.06046 (19)	−0.01633 (14)	0.23561 (18)	0.0365 (4)
H7	0.0287	0.0308	0.154	0.044*
C9	−0.0465 (2)	−0.03598 (16)	0.3089 (2)	0.0436 (5)
H9A	−0.0189	−0.0862	0.3864	0.052*
H9B	−0.0671	0.0294	0.35	0.052*
C8	0.10479 (17)	−0.11439 (14)	0.18042 (17)	0.0337 (4)
C1	0.2969 (2)	0.08524 (16)	0.2635 (2)	0.0427 (4)
C2	0.2703 (2)	0.16740 (18)	0.1666 (2)	0.0515 (5)
H2	0.1938	0.2026	0.1501	0.062*
C10	−0.1624 (2)	−0.0781 (2)	0.2036 (3)	0.0578 (6)
H10A	−0.2275	−0.0899	0.2522	0.087*
H10B	−0.1424	−0.1432	0.1638	0.087*
H10C	−0.1908	−0.0278	0.1279	0.087*
C3	0.3590 (2)	0.1965 (2)	0.0945 (2)	0.0581 (6)
H3	0.3411	0.2518	0.0292	0.07*
C6	0.4102 (3)	0.0344 (2)	0.2895 (3)	0.0708 (7)
H6	0.4284	−0.0204	0.3555	0.085*
C4	0.4722 (2)	0.1465 (2)	0.1164 (2)	0.0608 (6)
C5	0.4974 (3)	0.0658 (3)	0.2159 (4)	0.0845 (9)
H5	0.5748	0.0318	0.2339	0.101*
C11	0.5662 (3)	0.1790 (3)	0.0342 (3)	0.0942 (11)
H11A	0.5294	0.171	−0.0668	0.141*
H11B	0.6396	0.1353	0.0621	0.141*
H11C	0.5893	0.2513	0.0548	0.141*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0591 (3)	0.0407 (3)	0.0340 (3)	−0.0078 (2)	0.0135 (2)	−0.00587 (18)
N2	0.0653 (11)	0.0348 (8)	0.0342 (7)	0.0037 (8)	0.0189 (7)	−0.0008 (6)
O1	0.0757 (11)	0.0672 (11)	0.0348 (7)	−0.0118 (9)	0.0020 (7)	0.0072 (7)
O2	0.0804 (12)	0.0451 (9)	0.0688 (10)	−0.0142 (8)	0.0368 (9)	−0.0261 (8)
N3	0.0629 (11)	0.0394 (9)	0.0307 (7)	−0.0001 (8)	0.0190 (7)	−0.0034 (6)
N1	0.0576 (10)	0.0338 (8)	0.0265 (7)	0.0047 (7)	0.0156 (6)	0.0023 (6)
N4	0.0623 (11)	0.0383 (9)	0.0271 (7)	0.0005 (8)	0.0151 (7)	−0.0001 (6)
C7	0.0509 (11)	0.0299 (9)	0.0284 (8)	−0.0007 (8)	0.0095 (7)	−0.0003 (6)
C9	0.0545 (12)	0.0407 (11)	0.0395 (9)	0.0034 (9)	0.0189 (8)	−0.0039 (8)
C8	0.0444 (10)	0.0324 (9)	0.0252 (7)	−0.0025 (8)	0.0104 (7)	0.0011 (6)
C1	0.0478 (11)	0.0413 (10)	0.0385 (9)	−0.0020 (9)	0.0099 (8)	−0.0026 (8)
C2	0.0491 (12)	0.0525 (13)	0.0531 (11)	0.0066 (10)	0.0131 (9)	0.0091 (10)
C10	0.0544 (13)	0.0567 (14)	0.0620 (13)	−0.0029 (11)	0.0139 (10)	−0.0033 (11)
C3	0.0562 (14)	0.0657 (15)	0.0520 (12)	−0.0030 (12)	0.0125 (10)	0.0145 (11)
C6	0.0619 (15)	0.0762 (18)	0.0750 (16)	0.0211 (14)	0.0186 (13)	0.0248 (14)
C4	0.0464 (12)	0.0832 (18)	0.0525 (12)	−0.0079 (12)	0.0118 (10)	−0.0018 (12)
C5	0.0520 (15)	0.104 (2)	0.103 (2)	0.0254 (16)	0.0282 (15)	0.0254 (19)
C11	0.0635 (18)	0.137 (3)	0.091 (2)	−0.019 (2)	0.0344 (16)	0.001 (2)

Geometric parameters (Å, º)

S1—O1	1.4339 (16)	C1—C2	1.381 (3)
S1—O2	1.4364 (16)	C2—C3	1.381 (3)
S1—C1	1.764 (2)	C2—H2	0.93
S1—C7	1.8031 (19)	C10—H10A	0.96
N2—N3	1.293 (2)	C10—H10B	0.96
N2—N1	1.343 (2)	C10—H10C	0.96
N3—N4	1.355 (2)	C3—C4	1.366 (4)
N1—C8	1.335 (2)	C3—H3	0.93
N1—H1N	0.92 (2)	C6—C5	1.386 (4)
N4—C8	1.316 (2)	C6—H6	0.93
C7—C8	1.483 (2)	C4—C5	1.382 (4)
C7—C9	1.536 (3)	C4—C11	1.508 (4)
C7—H7	0.98	C5—H5	0.93
C9—C10	1.513 (3)	C11—H11A	0.96
C9—H9A	0.97	C11—H11B	0.96
C9—H9B	0.97	C11—H11C	0.96
C1—C6	1.368 (3)
O1—S1—O2	119.32 (10)	C2—C1—S1	119.38 (16)
O1—S1—C1	108.40 (10)	C1—C2—C3	119.0 (2)
O2—S1—C1	108.22 (10)	C1—C2—H2	120.5
O1—S1—C7	107.87 (9)	C3—C2—H2	120.5
O2—S1—C7	106.14 (10)	C9—C10—H10A	109.5
C1—S1—C7	106.16 (9)	C9—C10—H10B	109.5
N3—N2—N1	105.44 (15)	H10A—C10—H10B	109.5
N2—N3—N4	111.42 (14)	C9—C10—H10C	109.5
C8—N1—N2	109.35 (14)	H10A—C10—H10C	109.5
C8—N1—H1N	131.5 (14)	H10B—C10—H10C	109.5
N2—N1—H1N	119.2 (14)	C4—C3—C2	121.9 (2)
C8—N4—N3	105.76 (14)	C4—C3—H3	119
C8—C7—C9	112.73 (15)	C2—C3—H3	119
C8—C7—S1	111.59 (14)	C1—C6—C5	119.0 (2)
C9—C7—S1	108.51 (12)	C1—C6—H6	120.5
C8—C7—H7	107.9	C5—C6—H6	120.5
C9—C7—H7	107.9	C3—C4—C5	117.9 (2)
S1—C7—H7	107.9	C3—C4—C11	120.6 (3)
C10—C9—C7	111.21 (16)	C5—C4—C11	121.5 (3)
C10—C9—H9A	109.4	C4—C5—C6	121.6 (2)
C7—C9—H9A	109.4	C4—C5—H5	119.2
C10—C9—H9B	109.4	C6—C5—H5	119.2
C7—C9—H9B	109.4	C4—C11—H11A	109.5
H9A—C9—H9B	108	C4—C11—H11B	109.5
N4—C8—N1	108.03 (16)	H11A—C11—H11B	109.5
N4—C8—C7	126.14 (16)	C4—C11—H11C	109.5
N1—C8—C7	125.77 (14)	H11A—C11—H11C	109.5
C6—C1—C2	120.5 (2)	H11B—C11—H11C	109.5
C6—C1—S1	120.03 (18)
N1—N2—N3—N4	0.2 (2)	S1—C7—C8—N1	66.8 (2)
N3—N2—N1—C8	−0.2 (2)	O1—S1—C1—C6	6.6 (2)
N2—N3—N4—C8	−0.2 (2)	O2—S1—C1—C6	137.3 (2)
O1—S1—C7—C8	−53.64 (15)	C7—S1—C1—C6	−109.1 (2)
O2—S1—C7—C8	177.39 (12)	O1—S1—C1—C2	−170.24 (17)
C1—S1—C7—C8	62.38 (14)	O2—S1—C1—C2	−39.5 (2)
O1—S1—C7—C9	71.17 (16)	C7—S1—C1—C2	74.09 (19)
O2—S1—C7—C9	−57.80 (15)	C6—C1—C2—C3	1.0 (4)
C1—S1—C7—C9	−172.81 (13)	S1—C1—C2—C3	177.79 (18)
C8—C7—C9—C10	−63.8 (2)	C1—C2—C3—C4	0.0 (4)
S1—C7—C9—C10	172.07 (15)	C2—C1—C6—C5	−0.7 (4)
N3—N4—C8—N1	0.0 (2)	S1—C1—C6—C5	−177.5 (2)
N3—N4—C8—C7	−177.42 (18)	C2—C3—C4—C5	−1.2 (4)
N2—N1—C8—N4	0.1 (2)	C2—C3—C4—C11	179.0 (3)
N2—N1—C8—C7	177.58 (17)	C3—C4—C5—C6	1.5 (5)
C11—C7—C8—N4	121.3 (2)	C11—C4—C5—C6	−178.7 (3)
S1—C7—C8—N4	−116.25 (19)	C1—C6—C5—C4	−0.5 (5)
C11—C7—C8—N1	−55.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3^i	0.92 (2)	1.98 (2)	2.884 (2)	166 (2)

Symmetry code: (i) x, −y−1/2, z+1/2.

(2) 5-[1-(4-chlorphenylsulfonyl)ethyl]-1H-tetrazol

Crystal data

C9H9ClN4O2S	F(000) = 1120
Mr = 272.71	Dx = 1.526 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 5416 reflections
a = 9.7121 (2) Å	θ = 1–27.5°
b = 19.1953 (7) Å	µ = 0.49 mm^−1
c = 13.4438 (4) Å	T = 293 K
β = 108.737 (2)°	Plate, white
V = 2373.46 (12) Å^3	0.14 × 0.11 × 0.02 mm
Z = 8

Data collection

KappaCCD diffractometer	2925 reflections with I > 2σ(I)
CCD scans	Rint = 0.047
Absorption correction: multi-scan HKL Denzo and Scalepack (Otwinowski & Minor 1997)	θmax = 27.5°, θmin = 1.9°
Tmin = 0.94, Tmax = 0.99	h = −12→12
16855 measured reflections	k = −23→24
5416 independent reflections	l = −17→17

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.1761P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.054	(Δ/σ)max = 0.001
wR(F^2) = 0.136	Δρmax = 0.36 e Å^−3
S = 1.02	Δρmin = −0.37 e Å^−3
5416 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
316 parameters	Extinction coefficient: 0.0026 (7)
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cl11	1.23368 (9)	0.47041 (6)	0.41305 (7)	0.0777 (3)
S11	0.57463 (8)	0.40607 (4)	0.31104 (6)	0.0431 (2)
O11	0.5001 (2)	0.46932 (11)	0.31898 (17)	0.0584 (6)
O12	0.5559 (2)	0.34472 (11)	0.36688 (15)	0.0575 (6)
C14	1.0507 (3)	0.45300 (19)	0.3891 (2)	0.0477 (8)
C13	1.0084 (3)	0.38643 (19)	0.4036 (2)	0.0510 (8)
H13	1.0775	0.3516	0.4287	0.061*
C12	0.8626 (3)	0.37185 (17)	0.3805 (2)	0.0464 (8)
H12	0.8323	0.327	0.3894	0.056*
C11	0.7614 (3)	0.42455 (16)	0.3440 (2)	0.0398 (7)
C16	0.8051 (3)	0.49192 (16)	0.3315 (2)	0.0441 (7)
H16	0.7366	0.5271	0.308	0.053*
C15	0.9509 (3)	0.50609 (18)	0.3542 (2)	0.0506 (8)
H15	0.9818	0.551	0.3462	0.061*
C17	0.5134 (3)	0.38295 (15)	0.1726 (2)	0.0389 (7)
H17	0.4076	0.3889	0.1474	0.047*
C18	0.5418 (3)	0.30833 (15)	0.1594 (2)	0.0356 (7)
N11	0.4488 (3)	0.25661 (13)	0.15380 (19)	0.0439 (6)
H11N	0.361 (3)	0.2587 (14)	0.1592 (18)	0.041 (8)*
N12	0.5110 (3)	0.19586 (14)	0.1444 (2)	0.0528 (7)
N13	0.6406 (3)	0.21118 (15)	0.1446 (2)	0.0534 (7)
N14	0.6631 (2)	0.28096 (14)	0.15365 (18)	0.0439 (6)
C19	0.5739 (3)	0.43111 (16)	0.1066 (2)	0.0501 (8)
H19A	0.5514	0.4786	0.1179	0.075*
H19B	0.5309	0.4196	0.0336	0.075*
H19C	0.6774	0.4255	0.1266	0.075*
Cl21	−0.21840 (9)	0.59502 (7)	0.08306 (8)	0.0934 (4)
S21	0.43776 (8)	0.66151 (4)	0.18032 (5)	0.0408 (2)
O21	0.5138 (2)	0.59882 (11)	0.17306 (15)	0.0513 (6)
O22	0.4566 (2)	0.72268 (11)	0.12394 (15)	0.0553 (6)
C24	−0.0365 (3)	0.6126 (2)	0.1046 (2)	0.0532 (9)
C23	0.0618 (3)	0.55943 (19)	0.1281 (2)	0.0567 (9)
H23	0.0307	0.5137	0.1291	0.068*
C22	0.2083 (3)	0.57405 (17)	0.1504 (2)	0.0505 (8)
H22	0.2767	0.5384	0.1683	0.061*
C21	0.2517 (3)	0.64225 (16)	0.1458 (2)	0.0389 (7)
C26	0.1500 (3)	0.69601 (17)	0.1196 (2)	0.0462 (8)
H26	0.1793	0.7418	0.1161	0.055*
C25	0.0053 (3)	0.6801 (2)	0.0991 (2)	0.0520 (8)
H25	−0.0641	0.7153	0.0816	0.062*
C27	0.4936 (3)	0.68393 (15)	0.3185 (2)	0.0419 (7)
H27	0.5998	0.6803	0.3444	0.05*
C28	0.4585 (3)	0.75783 (15)	0.33175 (19)	0.0343 (7)
N21	0.5508 (3)	0.81094 (13)	0.34114 (18)	0.0409 (6)
H21N	0.646 (3)	0.8089 (16)	0.343 (2)	0.066 (10)*
N22	0.4836 (3)	0.87101 (13)	0.34909 (18)	0.0475 (6)
N23	0.3537 (3)	0.85409 (14)	0.34572 (18)	0.0475 (7)
N24	0.3341 (2)	0.78385 (14)	0.33473 (18)	0.0436 (6)
C29	0.4378 (4)	0.63338 (17)	0.3829 (2)	0.0589 (9)
H29A	0.4652	0.5868	0.3711	0.088*
H29B	0.3337	0.6365	0.3624	0.088*
H29C	0.4789	0.6447	0.456	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl11	0.0470 (5)	0.0986 (9)	0.0872 (6)	−0.0084 (5)	0.0213 (5)	−0.0056 (6)
S11	0.0482 (5)	0.0378 (5)	0.0521 (4)	−0.0013 (4)	0.0283 (4)	−0.0027 (4)
O11	0.0592 (13)	0.0436 (14)	0.0863 (15)	0.0059 (11)	0.0429 (12)	−0.0113 (12)
O12	0.0773 (16)	0.0486 (15)	0.0578 (12)	−0.0114 (12)	0.0375 (12)	0.0043 (11)
C14	0.0441 (18)	0.057 (2)	0.0425 (16)	−0.0030 (17)	0.0154 (15)	−0.0084 (16)
C13	0.048 (2)	0.054 (2)	0.0450 (17)	0.0102 (18)	0.0077 (15)	0.0035 (16)
C12	0.058 (2)	0.033 (2)	0.0479 (17)	−0.0018 (16)	0.0165 (16)	0.0004 (15)
C11	0.0458 (17)	0.038 (2)	0.0377 (15)	0.0005 (15)	0.0158 (14)	−0.0008 (14)
C16	0.0465 (18)	0.036 (2)	0.0513 (17)	0.0028 (15)	0.0172 (15)	0.0004 (15)
C15	0.056 (2)	0.043 (2)	0.0547 (19)	−0.0091 (17)	0.0212 (16)	−0.0038 (16)
C17	0.0302 (15)	0.0388 (19)	0.0468 (16)	0.0013 (13)	0.0109 (13)	0.0007 (14)
C18	0.0279 (15)	0.0363 (18)	0.0437 (15)	0.0001 (14)	0.0131 (13)	−0.0016 (14)
N11	0.0344 (14)	0.0405 (17)	0.0632 (16)	−0.0044 (13)	0.0245 (13)	−0.0051 (13)
N12	0.0508 (16)	0.0388 (18)	0.0716 (17)	−0.0014 (14)	0.0235 (14)	−0.0095 (14)
N13	0.0412 (15)	0.0487 (19)	0.0746 (17)	0.0028 (14)	0.0244 (14)	−0.0116 (15)
N14	0.0332 (13)	0.0413 (17)	0.0593 (15)	0.0009 (12)	0.0179 (12)	−0.0071 (13)
C19	0.061 (2)	0.043 (2)	0.0486 (17)	−0.0058 (17)	0.0201 (15)	0.0036 (15)
Cl21	0.0405 (5)	0.1428 (11)	0.0927 (7)	−0.0158 (6)	0.0154 (5)	0.0245 (7)
S21	0.0410 (4)	0.0381 (5)	0.0484 (4)	−0.0033 (4)	0.0217 (4)	−0.0049 (4)
O21	0.0503 (13)	0.0431 (14)	0.0696 (13)	0.0032 (11)	0.0322 (11)	−0.0110 (11)
O22	0.0685 (14)	0.0475 (14)	0.0572 (12)	−0.0121 (12)	0.0305 (11)	0.0031 (11)
C24	0.0365 (18)	0.076 (3)	0.0459 (17)	−0.0081 (19)	0.0113 (15)	0.0031 (18)
C23	0.050 (2)	0.058 (2)	0.061 (2)	−0.0142 (19)	0.0163 (17)	0.0023 (18)
C22	0.0485 (19)	0.040 (2)	0.062 (2)	0.0003 (17)	0.0175 (16)	−0.0016 (16)
C21	0.0398 (16)	0.0385 (19)	0.0398 (15)	−0.0033 (15)	0.0145 (13)	−0.0028 (14)
C26	0.0479 (19)	0.043 (2)	0.0425 (16)	0.0002 (16)	0.0074 (14)	−0.0041 (14)
C25	0.0421 (18)	0.060 (3)	0.0480 (18)	0.0111 (17)	0.0063 (15)	−0.0027 (17)
C27	0.0342 (15)	0.040 (2)	0.0513 (17)	0.0026 (14)	0.0134 (14)	−0.0033 (15)
C28	0.0291 (15)	0.0364 (19)	0.0382 (14)	−0.0021 (13)	0.0119 (12)	−0.0036 (13)
N21	0.0360 (14)	0.0367 (16)	0.0552 (15)	−0.0015 (13)	0.0218 (12)	−0.0052 (12)
N22	0.0536 (16)	0.0368 (17)	0.0580 (15)	−0.0014 (14)	0.0263 (13)	−0.0037 (13)
N23	0.0444 (15)	0.0449 (18)	0.0563 (15)	0.0043 (13)	0.0206 (13)	−0.0052 (13)
N24	0.0329 (13)	0.0447 (18)	0.0569 (15)	0.0004 (13)	0.0195 (12)	−0.0078 (13)
C29	0.077 (2)	0.050 (2)	0.0532 (18)	−0.0010 (19)	0.0262 (17)	0.0009 (17)

Geometric parameters (Å, º)

Cl11—C14	1.734 (3)	Cl21—C24	1.729 (3)
S11—O11	1.435 (2)	S21—O21	1.431 (2)
S11—O12	1.439 (2)	S21—O22	1.441 (2)
S11—C11	1.759 (3)	S21—C21	1.755 (3)
S11—C17	1.818 (3)	S21—C27	1.812 (3)
C14—C13	1.375 (4)	C24—C23	1.364 (4)
C14—C15	1.381 (4)	C24—C25	1.367 (5)
C13—C12	1.378 (4)	C23—C22	1.385 (4)
C13—H13	0.93	C23—H23	0.93
C12—C11	1.386 (4)	C22—C21	1.383 (4)
C12—H12	0.93	C22—H22	0.93
C11—C16	1.388 (4)	C21—C26	1.393 (4)
C16—C15	1.376 (4)	C26—C25	1.376 (4)
C16—H16	0.93	C26—H26	0.93
C15—H15	0.93	C25—H25	0.93
C17—C18	1.480 (4)	C27—C28	1.483 (4)
C17—C19	1.524 (3)	C27—C29	1.512 (4)
C17—H17	0.98	C27—H27	0.98
C18—N14	1.315 (3)	C28—N24	1.320 (3)
C18—N11	1.328 (3)	C28—N21	1.336 (3)
N11—N12	1.337 (3)	N21—N22	1.346 (3)
N11—H11N	0.88 (3)	N21—H21N	0.92 (3)
N12—N13	1.293 (3)	N22—N23	1.290 (3)
N13—N14	1.356 (3)	N23—N24	1.363 (3)
C19—H19A	0.96	C29—H29A	0.96
C19—H19B	0.96	C29—H29B	0.96
C19—H19C	0.96	C29—H29C	0.96
O11—S11—O12	120.16 (12)	O21—S21—O22	119.59 (12)
O11—S11—C11	108.33 (14)	O21—S21—C21	108.35 (13)
O12—S11—C11	109.04 (14)	O22—S21—C21	109.07 (14)
O11—S11—C17	106.01 (13)	O21—S21—C27	106.17 (13)
O12—S11—C17	106.25 (13)	O22—S21—C27	107.41 (13)
C11—S11—C17	106.19 (12)	C21—S21—C27	105.34 (12)
C13—C14—C15	121.6 (3)	C23—C24—C25	121.6 (3)
C13—C14—Cl11	119.2 (3)	C23—C24—Cl21	119.6 (3)
C15—C14—Cl11	119.1 (3)	C25—C24—Cl21	118.8 (3)
C14—C13—C12	119.3 (3)	C24—C23—C22	119.5 (3)
C14—C13—H13	120.4	C24—C23—H23	120.2
C12—C13—H13	120.4	C22—C23—H23	120.2
C13—C12—C11	119.5 (3)	C21—C22—C23	119.2 (3)
C13—C12—H12	120.3	C21—C22—H22	120.4
C11—C12—H12	120.3	C23—C22—H22	120.4
C12—C11—C16	120.9 (3)	C22—C21—C26	120.7 (3)
C12—C11—S11	119.9 (2)	C22—C21—S21	119.4 (2)
C16—C11—S11	119.2 (2)	C26—C21—S21	119.8 (2)
C15—C16—C11	119.4 (3)	C25—C26—C21	118.8 (3)
C15—C16—H16	120.3	C25—C26—H26	120.6
C11—C16—H16	120.3	C21—C26—H26	120.6
C16—C15—C14	119.3 (3)	C24—C25—C26	120.1 (3)
C16—C15—H15	120.3	C24—C25—H25	120
C14—C15—H15	120.3	C26—C25—H25	120
C18—C17—C19	113.3 (2)	C28—C27—C29	114.0 (2)
C18—C17—S11	110.28 (19)	C28—C27—S21	110.20 (19)
C19—C17—S11	112.8 (2)	C29—C27—S21	113.0 (2)
C18—C17—H17	106.6	C28—C27—H27	106.4
C19—C17—H17	106.6	C29—C27—H27	106.4
S11—C17—H17	106.6	S21—C27—H27	106.4
N14—C18—N11	107.7 (3)	N24—C28—N21	107.5 (3)
N14—C18—C17	126.8 (3)	N24—C28—C27	127.9 (3)
N11—C18—C17	125.5 (2)	N21—C28—C27	124.6 (2)
C18—N11—N12	109.8 (2)	C28—N21—N22	109.5 (2)
C18—N11—H11N	128.4 (18)	C28—N21—H21N	127 (2)
N12—N11—H11N	121.7 (18)	N22—N21—H21N	123 (2)
N13—N12—N11	105.7 (2)	N23—N22—N21	106.0 (2)
N12—N13—N14	110.7 (2)	N22—N23—N24	110.7 (2)
C18—N14—N13	106.2 (2)	C28—N24—N23	106.3 (2)
C17—C19—H19A	109.5	C27—C29—H29A	109.5
C17—C19—H19B	109.5	C27—C29—H29B	109.5
H19A—C19—H19B	109.5	H29A—C29—H29B	109.5
C17—C19—H19C	109.5	C27—C29—H29C	109.5
H19A—C19—H19C	109.5	H29A—C29—H29C	109.5
H19B—C19—H19C	109.5	H29B—C29—H29C	109.5
C15—C14—C13—C12	1.5 (4)	C25—C24—C23—C22	2.1 (5)
Cl11—C14—C13—C12	−177.35 (19)	Cl21—C24—C23—C22	−176.8 (2)
C14—C13—C12—C11	−0.5 (4)	C24—C23—C22—C21	−1.7 (4)
C13—C12—C11—C16	−0.7 (4)	C23—C22—C21—C26	0.4 (4)
C13—C12—C11—S11	178.4 (2)	C23—C22—C21—S21	176.9 (2)
O11—S11—C11—C12	156.0 (2)	O21—S21—C21—C22	20.3 (3)
O12—S11—C11—C12	23.6 (2)	O22—S21—C21—C22	152.0 (2)
C17—S11—C11—C12	−90.5 (2)	C27—S21—C21—C22	−93.0 (2)
O11—S11—C11—C16	−24.9 (2)	O21—S21—C21—C26	−163.2 (2)
O12—S11—C11—C16	−157.3 (2)	O22—S21—C21—C26	−31.5 (2)
C17—S11—C11—C16	88.6 (2)	C27—S21—C21—C26	83.5 (2)
C12—C11—C16—C15	1.0 (4)	C22—C21—C26—C25	0.5 (4)
S11—C11—C16—C15	−178.1 (2)	S21—C21—C26—C25	−176.03 (19)
C11—C16—C15—C14	0.0 (4)	C23—C24—C25—C26	−1.3 (5)
C13—C14—C15—C16	−1.2 (4)	Cl21—C24—C25—C26	177.7 (2)
Cl11—C14—C15—C16	177.6 (2)	C21—C26—C25—C24	0.0 (4)
O11—S11—C17—C18	−160.50 (17)	O21—S21—C27—C28	162.51 (18)
O12—S11—C17—C18	−31.6 (2)	O22—S21—C27—C28	33.5 (2)
C11—S11—C17—C18	84.4 (2)	C21—S21—C27—C28	−82.7 (2)
O11—S11—C17—C19	71.6 (2)	O21—S21—C27—C29	−68.7 (2)
O12—S11—C17—C19	−159.5 (2)	O22—S21—C27—C29	162.3 (2)
C11—S11—C17—C19	−43.4 (2)	C21—S21—C27—C29	46.1 (2)
C19—C17—C18—N14	41.7 (4)	C29—C27—C28—N24	−43.4 (4)
S11—C17—C18—N14	−85.9 (3)	S21—C27—C28—N24	84.9 (3)
C19—C17—C18—N11	−140.0 (3)	C29—C27—C28—N21	137.8 (3)
S11—C17—C18—N11	92.4 (3)	S21—C27—C28—N21	−93.9 (3)
N14—C18—N11—N12	0.0 (3)	N24—C28—N21—N22	−0.6 (3)
C17—C18—N11—N12	−178.5 (3)	C27—C28—N21—N22	178.4 (2)
C18—N11—N12—N13	0.1 (3)	C28—N21—N22—N23	0.7 (3)
N11—N12—N13—N14	−0.2 (3)	N21—N22—N23—N24	−0.5 (3)
N11—C18—N14—N13	−0.1 (3)	N21—C28—N24—N23	0.3 (3)
C17—C18—N14—N13	178.4 (3)	C27—C28—N24—N23	−178.7 (2)
N12—N13—N14—C18	0.2 (3)	N22—N23—N24—C28	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N24^i	0.88 (3)	1.98 (3)	2.849 (3)	168 (2)
N21—H21N···N14^ii	0.92 (3)	1.92 (3)	2.817 (3)	166 (3)

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

(3) 5-[1-(4-methoxophenylsulfonyl)propyl]-1H-tetrazol

Crystal data

C11H14N4O3S	F(000) = 1184
Mr = 282.32	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 6960 reflections
a = 9.8188 (2) Å	θ = 1.0–30.0°
b = 12.5801 (2) Å	µ = 0.26 mm^−1
c = 21.5687 (5) Å	T = 293 K
β = 99.339 (1)°	Plate, white
V = 2628.89 (9) Å^3	0.25 × 0.24 × 0.05 mm
Z = 8

Data collection

KappaCCD diffractometer	4077 reflections with I > 2σ(I)
CCD scans	Rint = 0.040
Absorption correction: multi-scan HKL Denzo and Scalepack (Otwinowski & Minor 1997)	θmax = 30.0°, θmin = 2.6°
Tmin = 0.94, Tmax = 0.99	h = −13→13
21761 measured reflections	k = −16→17
7607 independent reflections	l = −30→30

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.747P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.058	(Δ/σ)max < 0.001
wR(F^2) = 0.139	Δρmax = 0.21 e Å^−3
S = 1.02	Δρmin = −0.29 e Å^−3
7607 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
352 parameters	Extinction coefficient: 0.0031 (7)
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O13	0.95780 (19)	−0.1304 (2)	0.53118 (8)	0.0887 (7)
O23	0.47542 (19)	0.6583 (2)	0.53233 (9)	0.0954 (7)
C211	0.5797 (3)	0.7253 (3)	0.51917 (15)	0.0937 (11)
H21A	0.6508	0.7298	0.5553	0.112*
H21B	0.5424	0.7948	0.5089	0.112*
H21C	0.6178	0.6974	0.4842	0.112*
C111	1.0468 (3)	−0.2161 (3)	0.52395 (15)	0.1043 (12)
H11A	1.1173	−0.2207	0.5603	0.125*
H11B	1.0887	−0.2047	0.4873	0.125*
H11C	0.9949	−0.281	0.5194	0.125*
S11	0.47826 (5)	−0.03305 (4)	0.34019 (3)	0.04463 (17)
S21	−0.01692 (5)	0.56510 (5)	0.34616 (3)	0.04632 (17)
N21	0.06302 (17)	0.31198 (14)	0.32066 (8)	0.0389 (4)
H21	−0.016 (2)	0.298 (2)	0.3236 (11)	0.068 (8)*
N23	0.27298 (16)	0.28213 (14)	0.32071 (9)	0.0444 (4)
C28	0.11640 (17)	0.40033 (16)	0.30102 (9)	0.0337 (4)
N11	0.56324 (17)	0.21935 (14)	0.32029 (8)	0.0389 (4)
H11	0.484 (3)	0.232 (2)	0.3264 (11)	0.071 (8)*
N12	0.66293 (16)	0.29188 (14)	0.33413 (9)	0.0441 (4)
N22	0.16159 (16)	0.23763 (13)	0.33309 (9)	0.0437 (4)
C27	0.04039 (18)	0.49941 (16)	0.28083 (10)	0.0386 (5)
H27	0.1038	0.5474	0.2639	0.046*
N13	0.77295 (15)	0.24893 (14)	0.31909 (8)	0.0429 (4)
N14	0.74627 (15)	0.14915 (14)	0.29618 (8)	0.0425 (4)
O21	−0.09855 (15)	0.49102 (14)	0.37500 (8)	0.0625 (5)
N24	0.24906 (15)	0.38370 (14)	0.30052 (8)	0.0425 (4)
C18	0.61374 (17)	0.13206 (15)	0.29742 (9)	0.0342 (4)
O11	0.39372 (15)	0.04011 (13)	0.36838 (8)	0.0600 (5)
C17	0.53628 (18)	0.03459 (15)	0.27558 (10)	0.0372 (5)
H17	0.5992	−0.0131	0.2581	0.045*
O12	0.41945 (16)	−0.13200 (12)	0.31597 (8)	0.0608 (5)
O22	−0.07812 (15)	0.66376 (13)	0.32243 (8)	0.0632 (5)
C29	−0.08507 (19)	0.48022 (17)	0.22902 (10)	0.0446 (5)
H29A	−0.146	0.4287	0.2437	0.053*
H29B	−0.1359	0.5461	0.2204	0.053*
C21	0.1331 (2)	0.59327 (18)	0.39995 (10)	0.0447 (5)
C12	0.7148 (2)	−0.14107 (17)	0.38388 (10)	0.0446 (5)
H12	0.698	−0.1787	0.3463	0.054*
C19	0.41110 (19)	0.05498 (17)	0.22442 (10)	0.0427 (5)
H19A	0.3582	−0.0101	0.2164	0.051*
H19B	0.3521	0.108	0.2392	0.051*
C26	0.2199 (2)	0.67392 (18)	0.38801 (11)	0.0487 (6)
H26	0.2008	0.7123	0.3508	0.058*
C11	0.6265 (2)	−0.05972 (17)	0.39478 (10)	0.0432 (5)
C13	0.8277 (2)	−0.16664 (19)	0.42843 (10)	0.0488 (6)
H13	0.8872	−0.2208	0.4208	0.059*
C25	0.3360 (2)	0.6979 (2)	0.43156 (11)	0.0538 (6)
H25	0.395	0.7521	0.4235	0.065*
C110	0.4542 (2)	0.0931 (2)	0.16384 (11)	0.0582 (6)
H10A	0.3736	0.1052	0.133	0.07*
H10B	0.5111	0.0402	0.1487	0.07*
H10C	0.5053	0.1582	0.1715	0.07*
C24	0.3634 (2)	0.6409 (2)	0.48672 (12)	0.0640 (7)
C210	−0.0417 (2)	0.4400 (2)	0.16911 (11)	0.0612 (7)
H20A	−0.122	0.4289	0.138	0.073*
H20B	0.0073	0.3742	0.1773	0.073*
H20C	0.0173	0.4915	0.154	0.073*
C23	0.2734 (3)	0.5627 (3)	0.49930 (14)	0.0796 (9)
H23	0.2897	0.5267	0.5375	0.096*
C15	0.7625 (3)	−0.0297 (3)	0.49490 (13)	0.0782 (9)
H15	0.7782	0.0074	0.5327	0.094*
C16	0.6519 (3)	−0.0036 (2)	0.45024 (13)	0.0670 (7)
H16	0.5939	0.0519	0.4574	0.08*
C14	0.8514 (2)	−0.1112 (2)	0.48434 (11)	0.0594 (7)
C22	0.1603 (3)	0.5377 (2)	0.45590 (13)	0.0661 (7)
H22	0.1016	0.4833	0.4641	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0665 (12)	0.145 (2)	0.0498 (12)	0.0209 (13)	−0.0065 (9)	−0.0156 (12)
O23	0.0649 (12)	0.165 (2)	0.0537 (12)	−0.0244 (13)	0.0004 (10)	0.0165 (13)
C211	0.0677 (18)	0.139 (3)	0.071 (2)	−0.026 (2)	−0.0014 (15)	−0.013 (2)
C111	0.087 (2)	0.144 (3)	0.072 (2)	0.036 (2)	−0.0164 (17)	0.015 (2)
S11	0.0341 (3)	0.0440 (3)	0.0568 (4)	−0.0039 (2)	0.0108 (2)	0.0059 (3)
S21	0.0337 (3)	0.0447 (3)	0.0623 (4)	0.0021 (2)	0.0130 (3)	−0.0085 (3)
N21	0.0257 (8)	0.0371 (10)	0.0549 (12)	−0.0020 (7)	0.0094 (8)	0.0033 (8)
N23	0.0298 (8)	0.0429 (11)	0.0608 (12)	0.0059 (8)	0.0085 (8)	0.0029 (9)
C28	0.0256 (9)	0.0363 (11)	0.0402 (12)	−0.0002 (8)	0.0083 (8)	−0.0006 (9)
N11	0.0264 (8)	0.0354 (10)	0.0566 (12)	0.0000 (7)	0.0120 (8)	−0.0011 (8)
N12	0.0346 (9)	0.0389 (11)	0.0592 (12)	−0.0049 (8)	0.0089 (8)	−0.0018 (9)
N22	0.0333 (9)	0.0374 (10)	0.0606 (12)	0.0037 (8)	0.0086 (8)	0.0036 (9)
C27	0.0285 (9)	0.0354 (11)	0.0539 (13)	0.0005 (8)	0.0132 (9)	0.0022 (10)
N13	0.0292 (8)	0.0429 (11)	0.0567 (12)	−0.0051 (8)	0.0079 (8)	−0.0006 (9)
N14	0.0257 (8)	0.0442 (11)	0.0592 (12)	−0.0017 (7)	0.0119 (8)	−0.0037 (9)
O21	0.0469 (9)	0.0726 (12)	0.0757 (12)	−0.0131 (8)	0.0328 (8)	−0.0118 (9)
N24	0.0260 (8)	0.0429 (11)	0.0604 (12)	0.0014 (7)	0.0129 (8)	0.0026 (9)
C18	0.0252 (9)	0.0354 (11)	0.0424 (12)	0.0033 (8)	0.0071 (8)	0.0010 (9)
O11	0.0435 (8)	0.0705 (12)	0.0719 (12)	0.0094 (8)	0.0271 (8)	0.0102 (9)
C17	0.0289 (9)	0.0347 (12)	0.0501 (13)	−0.0005 (8)	0.0130 (9)	−0.0021 (9)
O12	0.0545 (9)	0.0461 (10)	0.0767 (12)	−0.0197 (8)	−0.0040 (8)	0.0120 (8)
O22	0.0531 (9)	0.0496 (10)	0.0821 (13)	0.0193 (8)	−0.0037 (8)	−0.0154 (9)
C29	0.0353 (10)	0.0449 (13)	0.0535 (14)	0.0084 (9)	0.0075 (10)	0.0056 (11)
C21	0.0395 (11)	0.0454 (13)	0.0510 (14)	0.0008 (10)	0.0131 (10)	−0.0003 (11)
C12	0.0466 (12)	0.0459 (13)	0.0420 (13)	−0.0002 (10)	0.0088 (10)	−0.0049 (10)
C19	0.0323 (10)	0.0442 (13)	0.0513 (14)	−0.0049 (9)	0.0060 (9)	−0.0018 (10)
C26	0.0448 (12)	0.0526 (15)	0.0502 (14)	−0.0022 (11)	0.0122 (10)	0.0026 (11)
C11	0.0419 (11)	0.0443 (13)	0.0443 (13)	−0.0042 (10)	0.0098 (9)	−0.0018 (10)
C13	0.0446 (12)	0.0544 (15)	0.0484 (15)	0.0067 (11)	0.0101 (10)	0.0009 (11)
C25	0.0477 (13)	0.0605 (16)	0.0564 (16)	−0.0140 (11)	0.0176 (11)	−0.0027 (12)
C110	0.0577 (14)	0.0633 (17)	0.0537 (15)	−0.0040 (12)	0.0090 (12)	0.0050 (13)
C24	0.0464 (13)	0.099 (2)	0.0472 (16)	−0.0024 (14)	0.0084 (12)	0.0038 (15)
C210	0.0623 (15)	0.0685 (17)	0.0531 (16)	0.0084 (13)	0.0102 (12)	0.0004 (13)
C23	0.0639 (17)	0.106 (2)	0.0673 (19)	−0.0070 (16)	0.0045 (14)	0.0376 (17)
C15	0.0667 (17)	0.106 (3)	0.0592 (18)	0.0127 (16)	0.0019 (14)	−0.0369 (17)
C16	0.0570 (15)	0.0723 (19)	0.0703 (19)	0.0121 (13)	0.0069 (13)	−0.0255 (15)
C14	0.0459 (13)	0.088 (2)	0.0433 (14)	−0.0002 (13)	0.0040 (11)	−0.0042 (13)
C22	0.0538 (14)	0.0677 (18)	0.0762 (19)	−0.0093 (13)	0.0083 (13)	0.0216 (15)

Geometric parameters (Å, º)

O13—C14	1.352 (3)	C17—C19	1.534 (3)
O13—C111	1.413 (4)	C17—H17	0.98
O23—C24	1.369 (3)	C29—C210	1.512 (3)
O23—C211	1.390 (3)	C29—H29A	0.97
C211—H21A	0.96	C29—H29B	0.97
C211—H21B	0.96	C21—C26	1.376 (3)
C211—H21C	0.96	C21—C22	1.382 (3)
C111—H11A	0.96	C12—C13	1.382 (3)
C111—H11B	0.96	C12—C11	1.386 (3)
C111—H11C	0.96	C12—H12	0.93
S11—O12	1.4346 (16)	C19—C110	1.515 (3)
S11—O11	1.4386 (15)	C19—H19A	0.97
S11—C11	1.750 (2)	C19—H19B	0.97
S11—C17	1.802 (2)	C26—C25	1.387 (3)
S21—O21	1.4351 (16)	C26—H26	0.93
S21—O22	1.4366 (16)	C11—C16	1.376 (3)
S21—C21	1.757 (2)	C13—C14	1.380 (3)
S21—C27	1.801 (2)	C13—H13	0.93
N21—C28	1.327 (2)	C25—C24	1.377 (3)
N21—N22	1.341 (2)	C25—H25	0.93
N21—H21	0.81 (2)	C110—H10A	0.96
N23—N22	1.295 (2)	C110—H10B	0.96
N23—N24	1.358 (2)	C110—H10C	0.96
C28—N24	1.321 (2)	C24—C23	1.379 (4)
C28—C27	1.481 (3)	C210—H20A	0.96
N11—C18	1.332 (2)	C210—H20B	0.96
N11—N12	1.336 (2)	C210—H20C	0.96
N11—H11	0.82 (2)	C23—C22	1.368 (4)
N12—N13	1.295 (2)	C23—H23	0.93
C27—C29	1.542 (3)	C15—C16	1.370 (4)
C27—H27	0.98	C15—C14	1.388 (4)
N13—N14	1.359 (2)	C15—H15	0.93
N14—C18	1.323 (2)	C16—H16	0.93
C18—C17	1.479 (3)	C22—H22	0.93
C14—O13—C111	118.1 (2)	C27—C29—H29A	109.3
C24—O23—C211	118.9 (2)	C210—C29—H29B	109.3
O23—C211—H21A	109.5	C27—C29—H29B	109.3
O23—C211—H21B	109.5	H29A—C29—H29B	108
H21A—C211—H21B	109.5	C26—C21—C22	119.9 (2)
O23—C211—H21C	109.5	C26—C21—S21	120.24 (18)
H21A—C211—H21C	109.5	C22—C21—S21	119.79 (18)
H21B—C211—H21C	109.5	C13—C12—C11	120.5 (2)
O13—C111—H11A	109.5	C13—C12—H12	119.8
O13—C111—H11B	109.5	C11—C12—H12	119.8
H11A—C111—H11B	109.5	C110—C19—C17	111.71 (16)
O13—C111—H11C	109.5	C110—C19—H19A	109.3
H11A—C111—H11C	109.5	C17—C19—H19A	109.3
H11B—C111—H11C	109.5	C110—C19—H19B	109.3
O12—S11—O11	118.90 (10)	C17—C19—H19B	109.3
O12—S11—C11	108.69 (10)	H19A—C19—H19B	107.9
O11—S11—C11	108.20 (10)	C21—C26—C25	119.9 (2)
O12—S11—C17	106.69 (10)	C21—C26—H26	120
O11—S11—C17	107.53 (9)	C25—C26—H26	120
C11—S11—C17	106.14 (9)	C16—C11—C12	119.7 (2)
O21—S21—O22	118.99 (10)	C16—C11—S11	119.99 (18)
O21—S21—C21	108.20 (11)	C12—C11—S11	120.17 (17)
O22—S21—C21	108.57 (10)	C14—C13—C12	119.5 (2)
O21—S21—C27	107.97 (10)	C14—C13—H13	120.3
O22—S21—C27	106.47 (10)	C12—C13—H13	120.3
C21—S21—C27	105.92 (9)	C24—C25—C26	119.7 (2)
C28—N21—N22	109.77 (15)	C24—C25—H25	120.1
C28—N21—H21	130.2 (18)	C26—C25—H25	120.1
N22—N21—H21	120.0 (18)	C19—C110—H10A	109.5
N22—N23—N24	111.41 (15)	C19—C110—H10B	109.5
N24—C28—N21	108.12 (17)	H10A—C110—H10B	109.5
N24—C28—C27	125.54 (17)	C19—C110—H10C	109.5
N21—C28—C27	126.31 (15)	H10A—C110—H10C	109.5
C18—N11—N12	110.03 (15)	H10B—C110—H10C	109.5
C18—N11—H11	129.1 (18)	O23—C24—C25	124.0 (2)
N12—N11—H11	120.8 (18)	O23—C24—C23	116.0 (2)
N13—N12—N11	105.65 (16)	C25—C24—C23	120.0 (2)
N23—N22—N21	105.28 (16)	C29—C210—H20A	109.5
C28—C27—C29	112.74 (17)	C29—C210—H20B	109.5
C28—C27—S21	111.26 (14)	H20A—C210—H20B	109.5
C29—C27—S21	108.94 (12)	C29—C210—H20C	109.5
C28—C27—H27	107.9	H20A—C210—H20C	109.5
C29—C27—H27	107.9	H20B—C210—H20C	109.5
S21—C27—H27	107.9	C22—C23—C24	120.3 (3)
N12—N13—N14	110.91 (15)	C22—C23—H23	119.9
C18—N14—N13	105.96 (15)	C24—C23—H23	119.9
C28—N24—N23	105.42 (15)	C16—C15—C14	120.6 (2)
N14—C18—N11	107.45 (17)	C16—C15—H15	119.7
N14—C18—C17	125.79 (17)	C14—C15—H15	119.7
N11—C18—C17	126.74 (15)	C15—C16—C11	120.0 (2)
C18—C17—C19	113.64 (17)	C15—C16—H16	120
C18—C17—S11	110.85 (14)	C11—C16—H16	120
C19—C17—S11	108.56 (12)	O13—C14—C13	124.3 (2)
C18—C17—H17	107.9	O13—C14—C15	116.1 (2)
C19—C17—H17	107.9	C13—C14—C15	119.7 (2)
S11—C17—H17	107.9	C23—C22—C21	120.1 (2)
C210—C29—C27	111.65 (16)	C23—C22—H22	119.9
C210—C29—H29A	109.3	C21—C22—H22	119.9
N22—N21—C28—N24	0.1 (2)	O22—S21—C21—C26	−39.9 (2)
N22—N21—C28—C27	178.05 (19)	C27—S21—C21—C26	74.09 (19)
C18—N11—N12—N13	0.6 (2)	O21—S21—C21—C22	6.4 (2)
N24—N23—N22—N21	0.0 (2)	O22—S21—C21—C22	136.8 (2)
C28—N21—N22—N23	−0.1 (2)	C27—S21—C21—C22	−109.2 (2)
N24—C28—C27—C29	123.8 (2)	C18—C17—C19—C110	66.6 (2)
N21—C28—C27—C29	−53.8 (3)	S11—C17—C19—C110	−169.53 (15)
N24—C28—C27—S21	−113.48 (19)	C22—C21—C26—C25	1.3 (3)
N21—C28—C27—S21	68.9 (2)	S21—C21—C26—C25	178.04 (16)
O21—S21—C27—C28	−56.02 (16)	C13—C12—C11—C16	0.3 (3)
O22—S21—C27—C28	175.13 (13)	C13—C12—C11—S11	−176.21 (16)
C21—S21—C27—C28	59.69 (16)	O12—S11—C11—C16	−137.7 (2)
O21—S21—C27—C29	68.86 (16)	O11—S11—C11—C16	−7.3 (2)
O22—S21—C27—C29	−59.98 (16)	C17—S11—C11—C16	107.9 (2)
C21—S21—C27—C29	−175.42 (14)	O12—S11—C11—C12	38.9 (2)
N11—N12—N13—N14	−0.5 (2)	O11—S11—C11—C12	169.28 (16)
N12—N13—N14—C18	0.3 (2)	C17—S11—C11—C12	−75.56 (19)
N21—C28—N24—N23	−0.1 (2)	C11—C12—C13—C14	0.6 (3)
C27—C28—N24—N23	−178.06 (19)	C21—C26—C25—C24	−0.3 (3)
N22—N23—N24—C28	0.1 (2)	C211—O23—C24—C25	−10.4 (4)
N13—N14—C18—N11	0.1 (2)	C211—O23—C24—C23	171.2 (3)
N13—N14—C18—C17	178.58 (19)	C26—C25—C24—O23	179.7 (2)
N12—N11—C18—N14	−0.5 (2)	C26—C25—C24—C23	−2.0 (4)
N12—N11—C18—C17	−178.90 (19)	O23—C24—C23—C22	−178.4 (3)
N14—C18—C17—C19	−122.5 (2)	C25—C24—C23—C22	3.2 (4)
N11—C18—C17—C19	55.7 (3)	C14—C15—C16—C11	1.3 (4)
N14—C18—C17—S11	114.9 (2)	C12—C11—C16—C15	−1.3 (4)
N11—C18—C17—S11	−66.9 (2)	S11—C11—C16—C15	175.3 (2)
O12—S11—C17—C18	−173.24 (13)	C111—O13—C14—C13	−3.3 (4)
O11—S11—C17—C18	58.17 (15)	C111—O13—C14—C15	176.7 (3)
C11—S11—C17—C18	−57.45 (15)	C12—C13—C14—O13	179.4 (2)
O12—S11—C17—C19	61.27 (16)	C12—C13—C14—C15	−0.6 (4)
O11—S11—C17—C19	−67.32 (16)	C16—C15—C14—O13	179.7 (3)
C11—S11—C17—C19	177.06 (14)	C16—C15—C14—C13	−0.3 (4)
C28—C27—C29—C210	−64.4 (2)	C24—C23—C22—C21	−2.1 (4)
S21—C27—C29—C210	171.63 (16)	C26—C21—C22—C23	−0.1 (4)
O21—S21—C21—C26	−170.35 (17)	S21—C21—C22—C23	−176.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N23	0.82 (2)	2.16 (2)	2.959 (2)	166 (2)
N21—H21···N13^i	0.81 (2)	2.15 (2)	2.951 (2)	172 (2)

Symmetry code: (i) x−1, y, z.

(4) 5-phenylsulfonyl-methylene-1H-tetrazol

Crystal data

C8H8N4O2S	F(000) = 464
Mr = 224.24	Dx = 1.468 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2yc	Cell parameters from 6531 reflections
a = 22.8887 (7) Å	θ = 1–35.0°
b = 5.0315 (2) Å	µ = 0.31 mm^−1
c = 9.1377 (3) Å	T = 293 K
β = 105.387 (2)°	Prism, yellow
V = 1014.62 (6) Å^3	0.33 × 0.25 × 0.1 mm
Z = 4

Data collection

KappaCCD diffractometer	3214 reflections with I > 2σ(I)
CCD scans	Rint = 0.031
Absorption correction: multi-scan HKL Denzo and Scalepack (Otwinowski & Minor 1997)	θmax = 34.9°, θmin = 3.7°
Tmin = 0.91, Tmax = 0.97	h = −36→36
14160 measured reflections	k = −6→8
4333 independent reflections	l = −14→14

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.3771P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max = 0.001
wR(F^2) = 0.116	Δρmax = 0.27 e Å^−3
S = 0.95	Δρmin = −0.29 e Å^−3
4333 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
139 parameters	Absolute structure parameter: −0.03 (7)
2 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.96060 (2)	0.86062 (8)	0.69897 (3)	0.03122 (10)
O1	0.97177 (7)	1.1417 (3)	0.7122 (2)	0.0433 (4)
O2	0.97208 (7)	0.7274 (3)	0.57008 (16)	0.0437 (3)
C7	1.00580 (9)	0.7050 (4)	0.8666 (2)	0.0334 (3)
H7A	1.002	0.8011	0.9557	0.04*
H7B	0.9921	0.5241	0.8731	0.04*
C8	1.06997 (9)	0.7045 (4)	0.8607 (3)	0.0366 (4)
C6	0.86002 (10)	0.9598 (5)	0.7939 (3)	0.0436 (4)
H6	0.8823	1.0968	0.8508	0.052*
C1	0.88569 (9)	0.7983 (4)	0.7044 (2)	0.0349 (4)
N1	1.10235 (9)	0.4908 (4)	0.8496 (3)	0.0529 (5)
H1N	1.0977 (14)	0.293 (6)	0.849 (4)	0.064*
C2	0.85355 (11)	0.5923 (5)	0.6187 (3)	0.0457 (5)
H2	0.8714	0.4858	0.5594	0.055*
C5	0.80076 (11)	0.9135 (6)	0.7971 (3)	0.0561 (6)
H5	0.7828	1.0191	0.8565	0.067*
N4	1.10346 (9)	0.9168 (4)	0.8585 (3)	0.0549 (5)
C4	0.76845 (11)	0.7086 (6)	0.7112 (4)	0.0578 (6)
H4	0.7285	0.6786	0.7128	0.069*
C3	0.79430 (13)	0.5484 (6)	0.6234 (4)	0.0577 (6)
H3	0.772	0.4107	0.5672	0.069*
N3	1.15797 (11)	0.8244 (5)	0.8472 (5)	0.0800 (9)
N2	1.15772 (12)	0.5681 (5)	0.8423 (5)	0.0822 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0392 (2)	0.02603 (16)	0.03223 (17)	0.00049 (19)	0.01616 (14)	0.00161 (19)
O1	0.0531 (11)	0.0240 (5)	0.0583 (10)	0.0012 (6)	0.0246 (9)	0.0063 (6)
O2	0.0540 (9)	0.0487 (8)	0.0334 (7)	0.0036 (7)	0.0201 (6)	−0.0042 (6)
C7	0.0387 (9)	0.0299 (8)	0.0349 (8)	−0.0008 (7)	0.0157 (7)	0.0025 (7)
C8	0.0374 (9)	0.0255 (7)	0.0477 (11)	−0.0010 (7)	0.0128 (8)	0.0004 (8)
C6	0.0412 (10)	0.0465 (11)	0.0463 (11)	0.0010 (9)	0.0174 (9)	−0.0046 (9)
C1	0.0376 (9)	0.0330 (9)	0.0360 (9)	0.0027 (7)	0.0127 (7)	0.0030 (7)
N1	0.0413 (10)	0.0294 (8)	0.0934 (17)	0.0008 (7)	0.0272 (10)	0.0009 (9)
C2	0.0430 (11)	0.0390 (11)	0.0548 (13)	−0.0033 (9)	0.0125 (10)	−0.0046 (10)
C5	0.0442 (12)	0.0647 (15)	0.0664 (16)	0.0038 (11)	0.0269 (11)	−0.0005 (13)
N4	0.0370 (9)	0.0329 (8)	0.0940 (16)	−0.0025 (7)	0.0161 (10)	0.0003 (10)
C4	0.0345 (11)	0.0674 (16)	0.0728 (16)	−0.0032 (10)	0.0166 (11)	0.0080 (14)
C3	0.0492 (13)	0.0479 (13)	0.0711 (17)	−0.0108 (11)	0.0074 (12)	−0.0018 (12)
N3	0.0401 (11)	0.0464 (12)	0.158 (3)	−0.0022 (9)	0.0349 (15)	0.0073 (15)
N2	0.0480 (12)	0.0462 (11)	0.163 (3)	0.0030 (11)	0.0461 (17)	0.0021 (17)

Geometric parameters (Å, º)

S1—O1	1.4367 (14)	C1—C2	1.386 (3)
S1—O2	1.4387 (14)	N1—N2	1.344 (3)
S1—C1	1.757 (2)	N1—H1N	1.00 (3)
S1—C7	1.786 (2)	C2—C3	1.386 (4)
C7—C8	1.484 (3)	C2—H2	0.93
C7—H7A	0.97	C5—C4	1.385 (4)
C7—H7B	0.97	C5—H5	0.93
C8—N4	1.318 (3)	N4—N3	1.361 (3)
C8—N1	1.325 (3)	C4—C3	1.377 (4)
C6—C5	1.384 (3)	C4—H4	0.93
C6—C1	1.390 (3)	C3—H3	0.93
C6—H6	0.93	N3—N2	1.290 (3)
O1—S1—O2	117.42 (11)	C6—C1—S1	118.71 (16)
O1—S1—C1	109.07 (9)	C8—N1—N2	108.8 (2)
O2—S1—C1	109.36 (10)	C8—N1—H1N	138.3 (18)
O1—S1—C7	108.04 (10)	N2—N1—H1N	112.8 (18)
O2—S1—C7	107.93 (9)	C3—C2—C1	118.6 (2)
C1—S1—C7	104.20 (9)	C3—C2—H2	120.7
C8—C7—S1	108.84 (13)	C1—C2—H2	120.7
C8—C7—H7A	109.9	C6—C5—C4	119.5 (2)
S1—C7—H7A	109.9	C6—C5—H5	120.3
C8—C7—H7B	109.9	C4—C5—H5	120.3
S1—C7—H7B	109.9	C8—N4—N3	105.86 (19)
H7A—C7—H7B	108.3	C3—C4—C5	121.2 (2)
N4—C8—N1	108.50 (19)	C3—C4—H4	119.4
N4—C8—C7	125.78 (18)	C5—C4—H4	119.4
N1—C8—C7	125.66 (18)	C4—C3—C2	120.0 (2)
C5—C6—C1	118.9 (2)	C4—C3—H3	120
C5—C6—H6	120.5	C2—C3—H3	120
C1—C6—H6	120.5	N2—N3—N4	110.4 (2)
C2—C1—C6	121.7 (2)	N3—N2—N1	106.4 (2)
C2—C1—S1	119.56 (16)
O1—S1—C7—C8	−73.79 (16)	N4—C8—N1—N2	0.8 (4)
O2—S1—C7—C8	54.12 (16)	C7—C8—N1—N2	178.0 (2)
C1—S1—C7—C8	170.31 (13)	C6—C1—C2—C3	0.0 (4)
S1—C7—C8—N4	62.9 (3)	S1—C1—C2—C3	−179.3 (2)
S1—C7—C8—N1	−113.8 (2)	C1—C6—C5—C4	−0.1 (4)
C5—C6—C1—C2	−0.1 (3)	N1—C8—N4—N3	−0.6 (3)
C5—C6—C1—S1	179.23 (19)	C7—C8—N4—N3	−177.8 (2)
O1—S1—C1—C2	145.58 (19)	C6—C5—C4—C3	0.5 (4)
O2—S1—C1—C2	15.9 (2)	C5—C4—C3—C2	−0.6 (4)
C7—S1—C1—C2	−99.24 (19)	C1—C2—C3—C4	0.3 (4)
O1—S1—C1—C6	−33.80 (19)	C8—N4—N3—N2	0.2 (4)
O2—S1—C1—C6	−163.44 (16)	N4—N3—N2—N1	0.3 (4)
C7—S1—C1—C6	81.38 (18)	C8—N1—N2—N3	−0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4^i	1.00 (3)	1.90 (3)	2.890 (3)	170 (3)

Symmetry code: (i) x, y−1, z.

(2a) 1-(4-chlorphenylsulfonyl)-ethyl-1-cyanide

Crystal data

C9H8ClNO2S	F(000) = 472
Mr = 229.67	Dx = 1.495 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 97 reflections
a = 7.0770 (6) Å	θ = 1–27.5°
b = 15.5895 (12) Å	µ = 0.55 mm^−1
c = 9.3409 (7) Å	T = 293 K
β = 98.114 (8)°	Prism, yellow
V = 1020.24 (14) Å^3	0.4 × 0.4 × 0.25 mm
Z = 4

Data collection

Automatic single crystal diffractometer KM4	Rint = 0.029
ω/2θ scan	θmax = 27.6°, θmin = 2.6°
5005 measured reflections	h = −9→9
2354 independent reflections	k = −20→20
2057 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters not defined?
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 0.3677P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.31 e Å^−3
2354 reflections	Δρmin = −0.22 e Å^−3
127 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.10494 (6)	0.31823 (3)	0.60158 (5)	0.04569 (15)
O1	0.0714 (2)	0.23528 (9)	0.65816 (17)	0.0604 (4)
O2	−0.0382 (2)	0.35765 (10)	0.49813 (18)	0.0674 (4)
Cl1	0.28760 (7)	0.56883 (4)	1.12078 (6)	0.06189 (18)
C4	0.2443 (2)	0.49909 (12)	0.9751 (2)	0.0441 (4)
C5	0.2643 (3)	0.41193 (12)	0.99914 (19)	0.0458 (4)
H5	0.303	0.3909	1.0918	0.055*
C6	0.2261 (2)	0.35660 (11)	0.88378 (19)	0.0424 (4)
H6	0.2401	0.2978	0.8977	0.051*
C1	0.1665 (2)	0.38919 (10)	0.74646 (18)	0.0394 (4)
C2	0.1495 (3)	0.47719 (11)	0.7235 (2)	0.0486 (4)
H2	0.1109	0.4985	0.631	0.058*
C3	0.1899 (3)	0.53235 (12)	0.8384 (2)	0.0514 (4)
H3	0.1808	0.5913	0.8243	0.062*
C7	0.3164 (3)	0.30820 (12)	0.51376 (19)	0.0475 (4)
H7	0.2877	0.2662	0.4357	0.057*
C9	0.3728 (4)	0.39135 (16)	0.4457 (3)	0.0719 (6)
H9A	0.2674	0.412	0.3785	0.086*
H9B	0.4801	0.3811	0.3957	0.086*
H9C	0.4064	0.4334	0.5199	0.086*
C8	0.4717 (3)	0.27246 (12)	0.61813 (19)	0.0467 (4)
N1	0.5880 (3)	0.24667 (15)	0.6977 (2)	0.0715 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0442 (2)	0.0395 (2)	0.0495 (3)	−0.00198 (18)	−0.00676 (18)	−0.00082 (17)
O1	0.0612 (9)	0.0422 (7)	0.0759 (10)	−0.0152 (6)	0.0030 (7)	−0.0005 (7)
O2	0.0597 (9)	0.0687 (10)	0.0650 (9)	0.0091 (7)	−0.0219 (7)	−0.0006 (8)
Cl1	0.0575 (3)	0.0658 (3)	0.0644 (3)	−0.0062 (2)	0.0156 (2)	−0.0241 (2)
C4	0.0378 (8)	0.0454 (9)	0.0506 (9)	−0.0010 (7)	0.0117 (7)	−0.0080 (8)
C5	0.0465 (9)	0.0504 (10)	0.0406 (9)	0.0023 (8)	0.0072 (7)	0.0049 (7)
C6	0.0455 (9)	0.0348 (8)	0.0470 (9)	0.0034 (7)	0.0070 (7)	0.0069 (7)
C1	0.0397 (8)	0.0351 (8)	0.0426 (8)	0.0020 (6)	0.0032 (7)	0.0014 (7)
C2	0.0581 (11)	0.0386 (9)	0.0472 (10)	0.0065 (8)	0.0011 (8)	0.0072 (7)
C3	0.0583 (11)	0.0337 (8)	0.0627 (11)	0.0051 (8)	0.0102 (9)	0.0023 (8)
C7	0.0589 (11)	0.0454 (9)	0.0360 (8)	0.0010 (8)	−0.0014 (7)	−0.0038 (7)
C9	0.0938 (18)	0.0649 (14)	0.0598 (13)	−0.0022 (13)	0.0208 (12)	0.0106 (11)
C8	0.0537 (10)	0.0471 (10)	0.0395 (9)	0.0034 (8)	0.0072 (8)	−0.0067 (7)
N1	0.0683 (12)	0.0875 (14)	0.0575 (11)	0.0171 (11)	0.0045 (9)	−0.0053 (10)

Geometric parameters (Å, º)

S1—O1	1.4293 (15)	C1—C2	1.391 (2)
S1—O2	1.4356 (14)	C2—C3	1.373 (3)
S1—C1	1.7546 (17)	C2—H2	0.93
S1—C7	1.812 (2)	C3—H3	0.93
Cl1—C4	1.7346 (18)	C7—C8	1.472 (3)
C4—C5	1.381 (3)	C7—C9	1.522 (3)
C4—C3	1.382 (3)	C7—H7	0.98
C5—C6	1.377 (2)	C9—H9A	0.96
C5—H5	0.93	C9—H9B	0.96
C6—C1	1.389 (2)	C9—H9C	0.96
C6—H6	0.93	C8—N1	1.104 (3)
O1—S1—O2	119.87 (9)	C3—C2—H2	120.2
O1—S1—C1	108.74 (9)	C1—C2—H2	120.2
O2—S1—C1	108.90 (9)	C2—C3—C4	119.17 (17)
O1—S1—C7	106.27 (9)	C2—C3—H3	120.4
O2—S1—C7	106.34 (10)	C4—C3—H3	120.4
C1—S1—C7	105.82 (8)	C8—C7—C9	112.58 (18)
C5—C4—C3	121.86 (17)	C8—C7—S1	108.66 (13)
C5—C4—Cl1	119.12 (15)	C9—C7—S1	113.44 (15)
C3—C4—Cl1	119.01 (15)	C8—C7—H7	107.3
C6—C5—C4	119.01 (16)	C9—C7—H7	107.3
C6—C5—H5	120.5	S1—C7—H7	107.3
C4—C5—H5	120.5	C7—C9—H9A	109.5
C5—C6—C1	119.61 (16)	C7—C9—H9B	109.5
C5—C6—H6	120.2	H9A—C9—H9B	109.5
C1—C6—H6	120.2	C7—C9—H9C	109.5
C6—C1—C2	120.76 (16)	H9A—C9—H9C	109.5
C6—C1—S1	119.45 (13)	H9B—C9—H9C	109.5
C2—C1—S1	119.76 (13)	N1—C8—C7	179.0 (2)
C3—C2—C1	119.55 (17)
C3—C4—C5—C6	−1.0 (3)	S1—C1—C2—C3	177.21 (15)
Cl1—C4—C5—C6	178.68 (13)	C1—C2—C3—C4	−0.9 (3)
C4—C5—C6—C1	−0.7 (3)	C5—C4—C3—C2	1.8 (3)
C5—C6—C1—C2	1.6 (3)	Cl1—C4—C3—C2	−177.88 (15)
C5—C6—C1—S1	−176.41 (14)	O1—S1—C7—C8	−54.38 (15)
O1—S1—C1—C6	17.65 (17)	O2—S1—C7—C8	176.85 (13)
O2—S1—C1—C6	149.87 (15)	C1—S1—C7—C8	61.12 (14)
C7—S1—C1—C6	−96.16 (15)	O1—S1—C7—C9	179.59 (15)
O1—S1—C1—C2	−160.38 (15)	O2—S1—C7—C9	50.83 (17)
O2—S1—C1—C2	−28.15 (19)	C1—S1—C7—C9	−64.90 (16)
C7—S1—C1—C2	85.81 (16)	C9—C7—C8—N1	65 (14)
C6—C1—C2—C3	−0.8 (3)	S1—C7—C8—N1	−61 (14)