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In the title compound, C13H11NO4S2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003346/sk1372sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003346/sk1372Isup2.hkl
Contains datablock I

CCDC reference: 146057

Computing details top

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
C13H11NO4S2F(000) = 640
Mr = 309.35Dx = 1.476 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2971 (4) ÅCell parameters from 2444 reflections
b = 7.0999 (4) Åθ = 1.5–25.0°
c = 27.0085 (15) ŵ = 0.39 mm1
β = 95.62 (1)°T = 293 K
V = 1392.55 (13) Å3Block, colourless
Z = 40.38 × 0.20 × 0.18 mm
Data collection top
Bruker SMART area detector
diffractometer
2444 independent reflections
Radiation source: fine-focus sealed X-ray tube1907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Peak integration from area–detector frames (SAINT; Bruker, 1999) scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 88
Tmin = 0.865, Tmax = 0.933k = 88
8612 measured reflectionsl = 2632
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.00Calculated w = 1/[σ2(Fo2) + (0.0486P)2]
where P = (Fo2 + 2Fc2)/3
2444 reflections(Δ/σ)max = 0.002
182 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.12940 (6)0.95061 (7)0.101469 (18)0.04962 (16)
O110.09066 (19)0.9791 (2)0.15172 (5)0.0647 (4)
O120.01575 (19)0.9573 (2)0.06178 (6)0.0735 (5)
S20.23278 (7)0.67765 (7)0.095716 (18)0.05410 (17)
C110.3111 (2)1.1000 (3)0.08880 (7)0.0438 (4)
C210.4349 (3)1.1613 (3)0.12751 (7)0.0517 (5)
C310.5885 (3)1.2604 (3)0.11678 (8)0.0553 (5)
C410.6213 (3)1.2998 (3)0.06807 (8)0.0523 (5)
C4110.7933 (3)1.4025 (3)0.05660 (10)0.0739 (7)
C510.4922 (3)1.2410 (3)0.03043 (7)0.0572 (5)
C610.3378 (3)1.1401 (3)0.03983 (7)0.0525 (5)
C120.3979 (2)0.6783 (2)0.14820 (7)0.0435 (4)
C220.3598 (2)0.6260 (3)0.19598 (7)0.0464 (4)
N220.1748 (2)0.5622 (3)0.20599 (7)0.0592 (5)
O2210.0933 (2)0.4512 (2)0.17726 (7)0.0785 (5)
O2220.1153 (2)0.6248 (3)0.24346 (6)0.0884 (6)
C320.4910 (3)0.6312 (3)0.23612 (8)0.0603 (6)
C420.6671 (3)0.6873 (3)0.22917 (9)0.0683 (6)
C520.7084 (3)0.7405 (3)0.18251 (9)0.0654 (6)
C620.5761 (3)0.7372 (3)0.14286 (8)0.0539 (5)
H210.41471.13600.16030.062*
H310.67201.30170.14270.066*
H41A0.88711.38720.08380.111*0.50
H41B0.76641.53400.05190.111*0.50
H41C0.83581.35160.02680.111*0.50
H41D0.77241.46130.02450.111*0.50
H41E0.89321.31450.05650.111*0.50
H41F0.82371.49690.08150.111*0.50
H510.51001.27050.00230.069*
H610.25371.09990.01390.063*
H320.46110.59730.26760.072*
H420.75790.68920.25590.082*
H520.82730.77920.17790.078*
H620.60650.77510.11170.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0434 (3)0.0591 (3)0.0467 (3)0.0008 (2)0.0062 (2)0.0057 (2)
O110.0653 (9)0.0765 (10)0.0566 (9)0.0017 (7)0.0271 (7)0.0019 (7)
O120.0501 (8)0.0948 (12)0.0724 (11)0.0035 (8)0.0107 (7)0.0192 (9)
S20.0671 (3)0.0489 (3)0.0459 (3)0.0117 (2)0.0037 (2)0.0026 (2)
C110.0479 (10)0.0417 (10)0.0423 (11)0.0039 (8)0.0071 (8)0.0023 (8)
C210.0684 (13)0.0470 (12)0.0402 (11)0.0022 (9)0.0072 (9)0.0005 (8)
C310.0629 (12)0.0470 (11)0.0538 (12)0.0083 (10)0.0052 (10)0.0039 (9)
C410.0555 (11)0.0394 (11)0.0631 (13)0.0012 (9)0.0115 (10)0.0023 (9)
C4110.0654 (14)0.0683 (15)0.0893 (17)0.0116 (12)0.0131 (13)0.0069 (13)
C510.0668 (13)0.0618 (13)0.0446 (12)0.0055 (11)0.0143 (10)0.0067 (10)
C610.0558 (12)0.0602 (13)0.0405 (11)0.0035 (9)0.0004 (9)0.0035 (9)
C120.0448 (10)0.0391 (10)0.0478 (11)0.0024 (8)0.0114 (8)0.0008 (8)
C220.0388 (10)0.0477 (11)0.0540 (12)0.0059 (8)0.0117 (9)0.0085 (9)
N220.0447 (9)0.0770 (13)0.0571 (11)0.0073 (9)0.0120 (9)0.0219 (10)
O2210.0657 (10)0.0801 (12)0.0908 (13)0.0226 (9)0.0131 (9)0.0141 (10)
O2220.0546 (9)0.1543 (18)0.0600 (10)0.0140 (10)0.0240 (8)0.0116 (10)
C320.0514 (12)0.0781 (16)0.0521 (13)0.0119 (10)0.0088 (10)0.0126 (11)
C420.0464 (12)0.0859 (17)0.0706 (15)0.0053 (11)0.0034 (11)0.0076 (13)
C520.0403 (11)0.0693 (15)0.0880 (17)0.0023 (10)0.0130 (11)0.0056 (13)
C620.0513 (11)0.0514 (12)0.0620 (13)0.0007 (9)0.0212 (10)0.0062 (10)
Geometric parameters (Å, º) top
S1—O111.4275 (15)C411—H41F0.9600
S1—O121.4320 (14)C51—C611.380 (3)
S1—C111.7575 (19)C51—H510.9300
S1—S22.0910 (8)C61—H610.9300
S2—C121.7683 (19)C12—C621.387 (2)
C11—C211.383 (3)C12—C221.397 (3)
C11—C611.385 (3)C22—C321.375 (3)
C21—C311.378 (3)C22—N221.474 (2)
C21—H210.9300N22—O2211.219 (2)
C31—C411.389 (3)N22—O2221.223 (2)
C31—H310.9300C32—C421.375 (3)
C41—C511.381 (3)C32—H320.9300
C41—C4111.510 (3)C42—C521.377 (3)
C411—H41A0.9600C42—H420.9300
C411—H41B0.9600C52—C621.370 (3)
C411—H41C0.9600C52—H520.9300
C411—H41D0.9600C62—H620.9300
C411—H41E0.9600
O11—S1—O12120.41 (10)C41—C411—H41F109.5
O11—S1—C11108.85 (9)H41A—C411—H41F56.3
O12—S1—C11110.56 (9)H41B—C411—H41F56.3
O11—S1—S2107.96 (7)H41C—C411—H41F141.1
O12—S1—S2102.75 (8)H41D—C411—H41F109.5
C11—S1—S2105.09 (6)H41E—C411—H41F109.5
C12—S2—S199.24 (6)C61—C51—C41122.14 (18)
C21—C11—C61120.95 (18)C61—C51—H51118.9
C21—C11—S1119.48 (14)C41—C51—H51118.9
C61—C11—S1119.30 (15)C51—C61—C11118.44 (19)
C31—C21—C11119.09 (18)C51—C61—H61120.8
C31—C21—H21120.5C11—C61—H61120.8
C11—C21—H21120.5C62—C12—C22116.72 (18)
C21—C31—C41121.42 (19)C62—C12—S2119.31 (15)
C21—C31—H31119.3C22—C12—S2123.95 (14)
C41—C31—H31119.3C32—C22—C12122.35 (17)
C51—C41—C31117.92 (18)C32—C22—N22116.33 (17)
C51—C41—C411121.0 (2)C12—C22—N22121.32 (18)
C31—C41—C411121.0 (2)O221—N22—O222124.84 (19)
C41—C411—H41A109.5O221—N22—C22118.70 (18)
C41—C411—H41B109.5O222—N22—C22116.5 (2)
H41A—C411—H41B109.5C22—C32—C42119.2 (2)
C41—C411—H41C109.5C22—C32—H32120.4
H41A—C411—H41C109.5C42—C32—H32120.4
H41B—C411—H41C109.5C32—C42—C52119.7 (2)
C41—C411—H41D109.5C32—C42—H42120.2
H41A—C411—H41D141.1C52—C42—H42120.2
H41B—C411—H41D56.3C62—C52—C42120.68 (19)
H41C—C411—H41D56.3C62—C52—H52119.7
C41—C411—H41E109.5C42—C52—H52119.7
H41A—C411—H41E56.3C52—C62—C12121.33 (19)
H41B—C411—H41E141.1C52—C62—H62119.3
H41C—C411—H41E56.3C12—C62—H62119.3
H41D—C411—H41E109.5
O11—S1—S2—C1247.92 (9)S1—C11—C61—C51173.24 (16)
O12—S1—S2—C12176.16 (9)S1—S2—C12—C6289.91 (15)
C11—S1—S2—C1268.13 (9)S1—S2—C12—C2288.75 (15)
O11—S1—C11—C2125.01 (18)C62—C12—C22—C320.2 (3)
O12—S1—C11—C21159.38 (15)S2—C12—C22—C32178.88 (16)
S2—S1—C11—C2190.42 (15)C62—C12—C22—N22179.66 (18)
O11—S1—C11—C61160.94 (15)S2—C12—C22—N221.0 (3)
O12—S1—C11—C6126.57 (19)C12—C22—N22—O22144.2 (3)
S2—S1—C11—C6183.62 (16)C32—C22—N22—O221135.9 (2)
C61—C11—C21—C311.3 (3)C12—C22—N22—O222136.55 (19)
S1—C11—C21—C31172.65 (15)C32—C22—N22—O22243.3 (2)
C11—C21—C31—C410.0 (3)C12—C22—C32—C420.9 (3)
C21—C31—C41—C511.7 (3)N22—C22—C32—C42179.2 (2)
C21—C31—C41—C411177.8 (2)C22—C32—C42—C521.2 (3)
C31—C41—C51—C612.4 (3)C32—C42—C52—C620.4 (4)
C411—C41—C51—C61177.2 (2)C42—C52—C62—C120.7 (3)
C41—C51—C61—C111.2 (3)C22—C12—C62—C521.0 (3)
C21—C11—C61—C510.7 (3)S2—C12—C62—C52179.78 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32···O11i0.932.403.324 (3)173
C52—H52···O11ii0.932.543.435 (3)160
C61—H61···012iii0.932.583.503 (3)171
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x, y+2, z.
 

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