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In the title compound, C
13H
11NO
4S
2, the nitro group is rotated by 44.1 (1)° out of the plane of the adjacent aryl ring and the toluenethiosulfonate group is almost orthogonal to the plane of the nitrated aryl ring. There are three types of C-H
O hydrogen bond in the structure [C
O range 3.324 (3)-3.503 (3) Å; C-H
O range 160-173°] and these link the molecules into a three-dimensional framework.
Supporting information
CCDC reference: 146057
Data collection: SAINT (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
S-(2-nitrophenyl)-4-toluenethiosulfonate
top
Crystal data top
C13H11NO4S2 | F(000) = 640 |
Mr = 309.35 | Dx = 1.476 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2971 (4) Å | Cell parameters from 2444 reflections |
b = 7.0999 (4) Å | θ = 1.5–25.0° |
c = 27.0085 (15) Å | µ = 0.39 mm−1 |
β = 95.62 (1)° | T = 293 K |
V = 1392.55 (13) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.20 × 0.18 mm |
Data collection top
Bruker SMART area detector diffractometer | 2444 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1907 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Peak integration from area–detector frames (SAINT; Bruker, 1999) scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −8→8 |
Tmin = 0.865, Tmax = 0.933 | k = −8→8 |
8612 measured reflections | l = −26→32 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.00 | Calculated w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3 |
2444 reflections | (Δ/σ)max = 0.002 |
182 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.12940 (6) | 0.95061 (7) | 0.101469 (18) | 0.04962 (16) | |
O11 | 0.09066 (19) | 0.9791 (2) | 0.15172 (5) | 0.0647 (4) | |
O12 | −0.01575 (19) | 0.9573 (2) | 0.06178 (6) | 0.0735 (5) | |
S2 | 0.23278 (7) | 0.67765 (7) | 0.095716 (18) | 0.05410 (17) | |
C11 | 0.3111 (2) | 1.1000 (3) | 0.08880 (7) | 0.0438 (4) | |
C21 | 0.4349 (3) | 1.1613 (3) | 0.12751 (7) | 0.0517 (5) | |
C31 | 0.5885 (3) | 1.2604 (3) | 0.11678 (8) | 0.0553 (5) | |
C41 | 0.6213 (3) | 1.2998 (3) | 0.06807 (8) | 0.0523 (5) | |
C411 | 0.7933 (3) | 1.4025 (3) | 0.05660 (10) | 0.0739 (7) | |
C51 | 0.4922 (3) | 1.2410 (3) | 0.03043 (7) | 0.0572 (5) | |
C61 | 0.3378 (3) | 1.1401 (3) | 0.03983 (7) | 0.0525 (5) | |
C12 | 0.3979 (2) | 0.6783 (2) | 0.14820 (7) | 0.0435 (4) | |
C22 | 0.3598 (2) | 0.6260 (3) | 0.19598 (7) | 0.0464 (4) | |
N22 | 0.1748 (2) | 0.5622 (3) | 0.20599 (7) | 0.0592 (5) | |
O221 | 0.0933 (2) | 0.4512 (2) | 0.17726 (7) | 0.0785 (5) | |
O222 | 0.1153 (2) | 0.6248 (3) | 0.24346 (6) | 0.0884 (6) | |
C32 | 0.4910 (3) | 0.6312 (3) | 0.23612 (8) | 0.0603 (6) | |
C42 | 0.6671 (3) | 0.6873 (3) | 0.22917 (9) | 0.0683 (6) | |
C52 | 0.7084 (3) | 0.7405 (3) | 0.18251 (9) | 0.0654 (6) | |
C62 | 0.5761 (3) | 0.7372 (3) | 0.14286 (8) | 0.0539 (5) | |
H21 | 0.4147 | 1.1360 | 0.1603 | 0.062* | |
H31 | 0.6720 | 1.3017 | 0.1427 | 0.066* | |
H41A | 0.8871 | 1.3872 | 0.0838 | 0.111* | 0.50 |
H41B | 0.7664 | 1.5340 | 0.0519 | 0.111* | 0.50 |
H41C | 0.8358 | 1.3516 | 0.0268 | 0.111* | 0.50 |
H41D | 0.7724 | 1.4613 | 0.0245 | 0.111* | 0.50 |
H41E | 0.8932 | 1.3145 | 0.0565 | 0.111* | 0.50 |
H41F | 0.8237 | 1.4969 | 0.0815 | 0.111* | 0.50 |
H51 | 0.5100 | 1.2705 | −0.0023 | 0.069* | |
H61 | 0.2537 | 1.0999 | 0.0139 | 0.063* | |
H32 | 0.4611 | 0.5973 | 0.2676 | 0.072* | |
H42 | 0.7579 | 0.6892 | 0.2559 | 0.082* | |
H52 | 0.8273 | 0.7792 | 0.1779 | 0.078* | |
H62 | 0.6065 | 0.7751 | 0.1117 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0434 (3) | 0.0591 (3) | 0.0467 (3) | −0.0008 (2) | 0.0062 (2) | 0.0057 (2) |
O11 | 0.0653 (9) | 0.0765 (10) | 0.0566 (9) | −0.0017 (7) | 0.0271 (7) | −0.0019 (7) |
O12 | 0.0501 (8) | 0.0948 (12) | 0.0724 (11) | −0.0035 (8) | −0.0107 (7) | 0.0192 (9) |
S2 | 0.0671 (3) | 0.0489 (3) | 0.0459 (3) | −0.0117 (2) | 0.0037 (2) | −0.0026 (2) |
C11 | 0.0479 (10) | 0.0417 (10) | 0.0423 (11) | 0.0039 (8) | 0.0071 (8) | 0.0023 (8) |
C21 | 0.0684 (13) | 0.0470 (12) | 0.0402 (11) | −0.0022 (9) | 0.0072 (9) | −0.0005 (8) |
C31 | 0.0629 (12) | 0.0470 (11) | 0.0538 (12) | −0.0083 (10) | −0.0052 (10) | −0.0039 (9) |
C41 | 0.0555 (11) | 0.0394 (11) | 0.0631 (13) | 0.0012 (9) | 0.0115 (10) | 0.0023 (9) |
C411 | 0.0654 (14) | 0.0683 (15) | 0.0893 (17) | −0.0116 (12) | 0.0131 (13) | 0.0069 (13) |
C51 | 0.0668 (13) | 0.0618 (13) | 0.0446 (12) | −0.0055 (11) | 0.0143 (10) | 0.0067 (10) |
C61 | 0.0558 (12) | 0.0602 (13) | 0.0405 (11) | −0.0035 (9) | 0.0004 (9) | 0.0035 (9) |
C12 | 0.0448 (10) | 0.0391 (10) | 0.0478 (11) | 0.0024 (8) | 0.0114 (8) | 0.0008 (8) |
C22 | 0.0388 (10) | 0.0477 (11) | 0.0540 (12) | 0.0059 (8) | 0.0117 (9) | 0.0085 (9) |
N22 | 0.0447 (9) | 0.0770 (13) | 0.0571 (11) | 0.0073 (9) | 0.0120 (9) | 0.0219 (10) |
O221 | 0.0657 (10) | 0.0801 (12) | 0.0908 (13) | −0.0226 (9) | 0.0131 (9) | 0.0141 (10) |
O222 | 0.0546 (9) | 0.1543 (18) | 0.0600 (10) | 0.0140 (10) | 0.0240 (8) | 0.0116 (10) |
C32 | 0.0514 (12) | 0.0781 (16) | 0.0521 (13) | 0.0119 (10) | 0.0088 (10) | 0.0126 (11) |
C42 | 0.0464 (12) | 0.0859 (17) | 0.0706 (15) | 0.0053 (11) | −0.0034 (11) | 0.0076 (13) |
C52 | 0.0403 (11) | 0.0693 (15) | 0.0880 (17) | −0.0023 (10) | 0.0130 (11) | 0.0056 (13) |
C62 | 0.0513 (11) | 0.0514 (12) | 0.0620 (13) | −0.0007 (9) | 0.0212 (10) | 0.0062 (10) |
Geometric parameters (Å, º) top
S1—O11 | 1.4275 (15) | C411—H41F | 0.9600 |
S1—O12 | 1.4320 (14) | C51—C61 | 1.380 (3) |
S1—C11 | 1.7575 (19) | C51—H51 | 0.9300 |
S1—S2 | 2.0910 (8) | C61—H61 | 0.9300 |
S2—C12 | 1.7683 (19) | C12—C62 | 1.387 (2) |
C11—C21 | 1.383 (3) | C12—C22 | 1.397 (3) |
C11—C61 | 1.385 (3) | C22—C32 | 1.375 (3) |
C21—C31 | 1.378 (3) | C22—N22 | 1.474 (2) |
C21—H21 | 0.9300 | N22—O221 | 1.219 (2) |
C31—C41 | 1.389 (3) | N22—O222 | 1.223 (2) |
C31—H31 | 0.9300 | C32—C42 | 1.375 (3) |
C41—C51 | 1.381 (3) | C32—H32 | 0.9300 |
C41—C411 | 1.510 (3) | C42—C52 | 1.377 (3) |
C411—H41A | 0.9600 | C42—H42 | 0.9300 |
C411—H41B | 0.9600 | C52—C62 | 1.370 (3) |
C411—H41C | 0.9600 | C52—H52 | 0.9300 |
C411—H41D | 0.9600 | C62—H62 | 0.9300 |
C411—H41E | 0.9600 | | |
| | | |
O11—S1—O12 | 120.41 (10) | C41—C411—H41F | 109.5 |
O11—S1—C11 | 108.85 (9) | H41A—C411—H41F | 56.3 |
O12—S1—C11 | 110.56 (9) | H41B—C411—H41F | 56.3 |
O11—S1—S2 | 107.96 (7) | H41C—C411—H41F | 141.1 |
O12—S1—S2 | 102.75 (8) | H41D—C411—H41F | 109.5 |
C11—S1—S2 | 105.09 (6) | H41E—C411—H41F | 109.5 |
C12—S2—S1 | 99.24 (6) | C61—C51—C41 | 122.14 (18) |
C21—C11—C61 | 120.95 (18) | C61—C51—H51 | 118.9 |
C21—C11—S1 | 119.48 (14) | C41—C51—H51 | 118.9 |
C61—C11—S1 | 119.30 (15) | C51—C61—C11 | 118.44 (19) |
C31—C21—C11 | 119.09 (18) | C51—C61—H61 | 120.8 |
C31—C21—H21 | 120.5 | C11—C61—H61 | 120.8 |
C11—C21—H21 | 120.5 | C62—C12—C22 | 116.72 (18) |
C21—C31—C41 | 121.42 (19) | C62—C12—S2 | 119.31 (15) |
C21—C31—H31 | 119.3 | C22—C12—S2 | 123.95 (14) |
C41—C31—H31 | 119.3 | C32—C22—C12 | 122.35 (17) |
C51—C41—C31 | 117.92 (18) | C32—C22—N22 | 116.33 (17) |
C51—C41—C411 | 121.0 (2) | C12—C22—N22 | 121.32 (18) |
C31—C41—C411 | 121.0 (2) | O221—N22—O222 | 124.84 (19) |
C41—C411—H41A | 109.5 | O221—N22—C22 | 118.70 (18) |
C41—C411—H41B | 109.5 | O222—N22—C22 | 116.5 (2) |
H41A—C411—H41B | 109.5 | C22—C32—C42 | 119.2 (2) |
C41—C411—H41C | 109.5 | C22—C32—H32 | 120.4 |
H41A—C411—H41C | 109.5 | C42—C32—H32 | 120.4 |
H41B—C411—H41C | 109.5 | C32—C42—C52 | 119.7 (2) |
C41—C411—H41D | 109.5 | C32—C42—H42 | 120.2 |
H41A—C411—H41D | 141.1 | C52—C42—H42 | 120.2 |
H41B—C411—H41D | 56.3 | C62—C52—C42 | 120.68 (19) |
H41C—C411—H41D | 56.3 | C62—C52—H52 | 119.7 |
C41—C411—H41E | 109.5 | C42—C52—H52 | 119.7 |
H41A—C411—H41E | 56.3 | C52—C62—C12 | 121.33 (19) |
H41B—C411—H41E | 141.1 | C52—C62—H62 | 119.3 |
H41C—C411—H41E | 56.3 | C12—C62—H62 | 119.3 |
H41D—C411—H41E | 109.5 | | |
| | | |
O11—S1—S2—C12 | −47.92 (9) | S1—C11—C61—C51 | −173.24 (16) |
O12—S1—S2—C12 | −176.16 (9) | S1—S2—C12—C62 | −89.91 (15) |
C11—S1—S2—C12 | 68.13 (9) | S1—S2—C12—C22 | 88.75 (15) |
O11—S1—C11—C21 | 25.01 (18) | C62—C12—C22—C32 | −0.2 (3) |
O12—S1—C11—C21 | 159.38 (15) | S2—C12—C22—C32 | −178.88 (16) |
S2—S1—C11—C21 | −90.42 (15) | C62—C12—C22—N22 | 179.66 (18) |
O11—S1—C11—C61 | −160.94 (15) | S2—C12—C22—N22 | 1.0 (3) |
O12—S1—C11—C61 | −26.57 (19) | C12—C22—N22—O221 | 44.2 (3) |
S2—S1—C11—C61 | 83.62 (16) | C32—C22—N22—O221 | −135.9 (2) |
C61—C11—C21—C31 | −1.3 (3) | C12—C22—N22—O222 | −136.55 (19) |
S1—C11—C21—C31 | 172.65 (15) | C32—C22—N22—O222 | 43.3 (2) |
C11—C21—C31—C41 | 0.0 (3) | C12—C22—C32—C42 | −0.9 (3) |
C21—C31—C41—C51 | 1.7 (3) | N22—C22—C32—C42 | 179.2 (2) |
C21—C31—C41—C411 | −177.8 (2) | C22—C32—C42—C52 | 1.2 (3) |
C31—C41—C51—C61 | −2.4 (3) | C32—C42—C52—C62 | −0.4 (4) |
C411—C41—C51—C61 | 177.2 (2) | C42—C52—C62—C12 | −0.7 (3) |
C41—C51—C61—C11 | 1.2 (3) | C22—C12—C62—C52 | 1.0 (3) |
C21—C11—C61—C51 | 0.7 (3) | S2—C12—C62—C52 | 179.78 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32···O11i | 0.93 | 2.40 | 3.324 (3) | 173 |
C52—H52···O11ii | 0.93 | 2.54 | 3.435 (3) | 160 |
C61—H61···012iii | 0.93 | 2.58 | 3.503 (3) | 171 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, −y+2, −z. |
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