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.
Supporting information
CCDC references: 718184; 718185; 718186; 718187; 718188
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]-1
H-tetrazol
top
Crystal data top
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) Å3 | 0.35 × 0.15 × 0.13 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4433P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.049 | (Δ/σ)max < 0.001 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
168 parameters | Extinction coefficient: 0.034 (4) |
0 restraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N3i | 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]-1
H-tetrazol
top
Crystal data top
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) Å3 | 0.14 × 0.11 × 0.02 mm |
Z = 8 | |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1761P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.054 | (Δ/σ)max = 0.001 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
316 parameters | Extinction coefficient: 0.0026 (7) |
0 restraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11N···N24i | 0.88 (3) | 1.98 (3) | 2.849 (3) | 168 (2) |
N21—H21N···N14ii | 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]-1
H-tetrazol
top
Crystal data top
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) Å3 | 0.25 × 0.24 × 0.05 mm |
Z = 8 | |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.047P)2 + 0.747P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.058 | (Δ/σ)max < 0.001 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
352 parameters | Extinction coefficient: 0.0031 (7) |
0 restraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···N13i | 0.81 (2) | 2.15 (2) | 2.951 (2) | 172 (2) |
Symmetry code: (i) x−1, y, z. |
(4) 5-phenylsulfonyl-methylene-1
H-tetrazol
top
Crystal data top
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) Å3 | 0.33 × 0.25 × 0.1 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.3771P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.045 | (Δ/σ)max = 0.001 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N4i | 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
top
Crystal data top
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) Å3 | 0.4 × 0.4 × 0.25 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters not defined? |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0469P)2 + 0.3677P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |