Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106021524/hj3013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106021524/hj3013Isup2.hkl |
CCDC reference: 618617
All reactions were carried out under an atmosphere of purified nitrogen. Solvents used were dried and distilled prior to use. 2,4-Dinitrophenylsulfenyl chloride and phthalimide were purchased from Aldrich. The precursor compound, C14H7N3O6S, was prepared according to the method of Wunderly (1972). A solution of 2,4-dinitrophenyl chloride (2.487 g, 0.008 mol) in dry methanol (80 ml) was added dropwise to a stirred solution of phthalimide (1.176 g, 0.008 mol) and triethylamine (1.49 ml, 0.008 mol) in dimethylformamide (5 ml) under a nitrogen atmosphere. Stirring was continued for 30 min at 298 K. Cold destilled water (100 ml) was added and stirring was continued for a further 30 min. The yellow precipitate which formed was filtered off, washed with pentane and dried at room temperature. The title compound, C10H11N3O5S, (I), was prepared according to the method of Harpp & Back (1971). Orange crystals of (I) suitable for X-ray studies were obtained by slow evaporation of a solution of the product in diethyl ether.
H atoms were positioned geometrically and refined using a riding model, with Uiso(H) = 1.2Ueq(C) (Caromatic—H = 0.93 Å and Cmethylene—H = 0.97 Å). The material was difficult to obtain in a suitable crystalline form and the best available specimen was lost late in the data collection, resulting in 97% completeness after merging equivalents.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C10H11N3O5S | F(000) = 592 |
Mr = 285.28 | Dx = 1.521 Mg m−3 |
Monoclinic, P21/c | Melting point: 196.4 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4280 (2) Å | Cell parameters from 6390 reflections |
b = 16.0850 (7) Å | θ = 2.1–27.9° |
c = 12.1500 (6) Å | µ = 0.28 mm−1 |
β = 97.4900 (16)° | T = 298 K |
V = 1245.52 (9) Å3 | Prism, orange |
Z = 4 | 0.40 × 0.25 × 0.18 mm |
Nonius KappaCCD area-detector diffractometer | 2901 independent reflections |
Radiation source: fine-focus sealed tube | 2311 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
ϕ scans, and ω scans with κ offsets | θmax = 27.9°, θmin = 2.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −8→7 |
Tmin = 0.915, Tmax = 0.950 | k = −21→19 |
7918 measured reflections | l = −16→12 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.069 | w = 1/[σ2(Fo2) + (0.1026P)2 + 0.3584P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.206 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.37 e Å−3 |
2901 reflections | Δρmin = −0.37 e Å−3 |
172 parameters |
C10H11N3O5S | V = 1245.52 (9) Å3 |
Mr = 285.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.4280 (2) Å | µ = 0.28 mm−1 |
b = 16.0850 (7) Å | T = 298 K |
c = 12.1500 (6) Å | 0.40 × 0.25 × 0.18 mm |
β = 97.4900 (16)° |
Nonius KappaCCD area-detector diffractometer | 2901 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2311 reflections with I > 2σ(I) |
Tmin = 0.915, Tmax = 0.950 | Rint = 0.086 |
7918 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.37 e Å−3 |
2901 reflections | Δρmin = −0.37 e Å−3 |
172 parameters |
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. Mean-plane data from final SHELXL refinement run: Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) −3.3714(0.0264)x + 10.5066(0.0237)y + 7.4096(0.0391)z = 5.9233(0.0055) * 0.0000 (0.0000) O2 * 0.0000 (0.0000) N2 * 0.0000 (0.0000) O3 Rms deviation of fitted atoms = 0.0000 −3.3269(0.0051)x + 11.1616(0.0103)y + 6.8502(0.0094)z = 5.8081(0.0041) A ngle to previous plane (with approximate e.s.d.) = 3.52(0.41) * −0.0095 (0.0015) C5 * 0.0036 (0.0015) C6 * 0.0056 (0.0015) C7 * −0.0089 (0.0016) C8 * 0.0025 (0.0017) C9 * 0.0067 (0.0017) C10 − 0.0424 (0.0035) N3 0.0218 (0.0035) N2 − 0.0910 (0.0030) S1 Rms deviation of fitted atoms = 0.0067 −2.8459(0.0250)x + 11.0671(0.0527)y + 7.6275(0.0228)z = 6.2840(0.0200) A ngle to previous plane (with approximate e.s.d.) = 6.06(0.45) * 0.0000 (0.0000) O5 * 0.0000 (0.0000) N3 * 0.0000 (0.0000) O4 Rms deviation of fitted atoms = 0.0000 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.28752 (10) | 0.07516 (5) | 0.57249 (6) | 0.0556 (3) | |
O1 | −0.1272 (4) | −0.06892 (13) | 0.8830 (2) | 0.0744 (7) | |
O2 | −0.4449 (4) | 0.14649 (19) | 0.3893 (2) | 0.0884 (8) | |
O3 | −0.3347 (4) | 0.24689 (18) | 0.2970 (2) | 0.0899 (8) | |
O4 | 0.5261 (3) | 0.32752 (16) | 0.5449 (2) | 0.0762 (7) | |
O5 | 0.3200 (4) | 0.37217 (15) | 0.40325 (19) | 0.0720 (6) | |
N1 | −0.1800 (3) | 0.03842 (14) | 0.69808 (18) | 0.0514 (6) | |
N2 | −0.3142 (3) | 0.19874 (16) | 0.37465 (19) | 0.0554 (6) | |
N3 | 0.3595 (3) | 0.32676 (15) | 0.4839 (2) | 0.0526 (6) | |
C1 | 0.0267 (5) | −0.0637 (2) | 0.8098 (3) | 0.0702 (9) | |
H1A | 0.0982 | −0.1167 | 0.8082 | 0.084* | |
H1B | 0.13 | −0.0221 | 0.8368 | 0.084* | |
C2 | −0.0696 (5) | −0.04138 (18) | 0.6945 (3) | 0.0597 (7) | |
H2A | 0.0388 | −0.0369 | 0.6463 | 0.072* | |
H2B | −0.1674 | −0.0843 | 0.6652 | 0.072* | |
C3 | −0.3366 (5) | 0.03413 (18) | 0.7767 (3) | 0.0617 (8) | |
H3A | −0.4447 | −0.0059 | 0.7506 | 0.074* | |
H3B | −0.4025 | 0.088 | 0.7817 | 0.074* | |
C4 | −0.2309 (6) | 0.0090 (2) | 0.8872 (3) | 0.0729 (9) | |
H4A | −0.1293 | 0.0511 | 0.9147 | 0.088* | |
H4B | −0.334 | 0.0052 | 0.9386 | 0.088* | |
C5 | −0.1028 (3) | 0.15150 (14) | 0.54972 (19) | 0.0397 (5) | |
C6 | −0.1267 (3) | 0.20323 (15) | 0.45573 (18) | 0.0407 (5) | |
C7 | 0.0213 (3) | 0.26079 (15) | 0.43413 (19) | 0.0414 (5) | |
H7 | 0.0006 | 0.2942 | 0.3712 | 0.05* | |
C8 | 0.2000 (3) | 0.26718 (15) | 0.50838 (19) | 0.0401 (5) | |
C9 | 0.2318 (3) | 0.21931 (17) | 0.60350 (19) | 0.0449 (6) | |
H9 | 0.3536 | 0.2255 | 0.6533 | 0.054* | |
C10 | 0.0820 (4) | 0.16247 (15) | 0.62395 (19) | 0.0437 (5) | |
H10 | 0.1032 | 0.1306 | 0.6883 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0488 (4) | 0.0610 (5) | 0.0569 (5) | −0.0164 (3) | 0.0064 (3) | −0.0080 (3) |
O1 | 0.0940 (16) | 0.0520 (12) | 0.0837 (16) | 0.0128 (11) | 0.0368 (13) | 0.0186 (11) |
O2 | 0.0587 (13) | 0.120 (2) | 0.0787 (16) | −0.0279 (13) | −0.0213 (11) | −0.0049 (14) |
O3 | 0.0905 (16) | 0.0885 (18) | 0.0759 (15) | 0.0047 (13) | −0.0444 (12) | 0.0135 (13) |
O4 | 0.0486 (11) | 0.0835 (15) | 0.0938 (17) | −0.0204 (10) | −0.0008 (10) | 0.0052 (13) |
O5 | 0.0788 (14) | 0.0718 (14) | 0.0684 (14) | −0.0115 (11) | 0.0206 (11) | 0.0174 (11) |
N1 | 0.0563 (12) | 0.0447 (12) | 0.0570 (13) | −0.0007 (9) | 0.0222 (10) | −0.0008 (10) |
N2 | 0.0457 (11) | 0.0656 (15) | 0.0499 (13) | 0.0062 (10) | −0.0121 (9) | −0.0143 (11) |
N3 | 0.0501 (12) | 0.0501 (12) | 0.0595 (14) | −0.0057 (9) | 0.0139 (10) | −0.0034 (11) |
C1 | 0.0680 (18) | 0.0626 (19) | 0.083 (2) | 0.0130 (14) | 0.0207 (16) | 0.0092 (16) |
C2 | 0.0597 (15) | 0.0498 (15) | 0.0739 (19) | 0.0046 (12) | 0.0250 (14) | −0.0088 (13) |
C3 | 0.0713 (17) | 0.0479 (15) | 0.0730 (19) | 0.0042 (13) | 0.0360 (15) | 0.0003 (13) |
C4 | 0.100 (2) | 0.0549 (17) | 0.071 (2) | 0.0143 (16) | 0.0378 (18) | 0.0082 (15) |
C5 | 0.0372 (11) | 0.0427 (12) | 0.0390 (12) | −0.0014 (8) | 0.0042 (8) | −0.0099 (9) |
C6 | 0.0371 (11) | 0.0456 (12) | 0.0368 (11) | 0.0056 (9) | −0.0042 (8) | −0.0090 (10) |
C7 | 0.0472 (12) | 0.0418 (12) | 0.0342 (11) | 0.0073 (9) | 0.0015 (9) | −0.0006 (9) |
C8 | 0.0389 (11) | 0.0404 (12) | 0.0409 (12) | −0.0017 (9) | 0.0053 (9) | −0.0036 (9) |
C9 | 0.0391 (11) | 0.0511 (13) | 0.0413 (12) | −0.0029 (9) | −0.0068 (9) | −0.0019 (10) |
C10 | 0.0468 (12) | 0.0465 (13) | 0.0351 (11) | −0.0032 (10) | −0.0040 (9) | 0.0009 (10) |
S1—N1 | 1.697 (2) | C2—H2B | 0.97 |
S1—C5 | 1.755 (2) | C3—C4 | 1.481 (5) |
O1—C1 | 1.417 (4) | C3—H3A | 0.97 |
O1—C4 | 1.423 (4) | C3—H3B | 0.97 |
O2—N2 | 1.218 (3) | C4—H4A | 0.97 |
O3—N2 | 1.214 (3) | C4—H4B | 0.97 |
O4—N3 | 1.220 (3) | C5—C6 | 1.405 (3) |
O5—N3 | 1.222 (3) | C5—C10 | 1.406 (3) |
N1—C2 | 1.470 (4) | C6—C7 | 1.377 (3) |
N1—C3 | 1.477 (3) | C7—C8 | 1.369 (3) |
N2—C6 | 1.456 (3) | C7—H7 | 0.93 |
N3—C8 | 1.462 (3) | C8—C9 | 1.382 (3) |
C1—C2 | 1.500 (5) | C9—C10 | 1.374 (3) |
C1—H1A | 0.97 | C9—H9 | 0.93 |
C1—H1B | 0.97 | C10—H10 | 0.93 |
C2—H2A | 0.97 | ||
N1—S1—C5 | 100.41 (11) | C4—C3—H3B | 109.8 |
C1—O1—C4 | 109.8 (2) | H3A—C3—H3B | 108.3 |
C2—N1—C3 | 110.5 (2) | O1—C4—C3 | 111.7 (3) |
C2—N1—S1 | 114.76 (19) | O1—C4—H4A | 109.3 |
C3—N1—S1 | 111.44 (19) | C3—C4—H4A | 109.3 |
O3—N2—O2 | 123.1 (2) | O1—C4—H4B | 109.3 |
O3—N2—C6 | 119.4 (2) | C3—C4—H4B | 109.3 |
O2—N2—C6 | 117.5 (2) | H4A—C4—H4B | 107.9 |
O4—N3—O5 | 123.7 (2) | C6—C5—C10 | 116.2 (2) |
O4—N3—C8 | 117.8 (2) | C6—C5—S1 | 122.54 (17) |
O5—N3—C8 | 118.5 (2) | C10—C5—S1 | 121.28 (19) |
O1—C1—C2 | 111.3 (3) | C7—C6—C5 | 123.2 (2) |
O1—C1—H1A | 109.4 | C7—C6—N2 | 115.9 (2) |
C2—C1—H1A | 109.4 | C5—C6—N2 | 120.9 (2) |
O1—C1—H1B | 109.4 | C8—C7—C6 | 117.8 (2) |
C2—C1—H1B | 109.4 | C8—C7—H7 | 121.1 |
H1A—C1—H1B | 108 | C6—C7—H7 | 121.1 |
N1—C2—C1 | 108.9 (2) | C7—C8—C9 | 122.0 (2) |
N1—C2—H2A | 109.9 | C7—C8—N3 | 117.8 (2) |
C1—C2—H2A | 109.9 | C9—C8—N3 | 120.3 (2) |
N1—C2—H2B | 109.9 | C10—C9—C8 | 119.4 (2) |
C1—C2—H2B | 109.9 | C10—C9—H9 | 120.3 |
H2A—C2—H2B | 108.3 | C8—C9—H9 | 120.3 |
N1—C3—C4 | 109.2 (3) | C9—C10—C5 | 121.4 (2) |
N1—C3—H3A | 109.8 | C9—C10—H10 | 119.3 |
C4—C3—H3A | 109.8 | C5—C10—H10 | 119.3 |
N1—C3—H3B | 109.8 | ||
C5—S1—N1—C2 | −102.4 (2) | O2—N2—C6—C7 | 177.5 (2) |
C5—S1—N1—C3 | 131.02 (18) | O3—N2—C6—C5 | 176.6 (2) |
C4—O1—C1—C2 | −59.9 (4) | O2—N2—C6—C5 | −2.7 (3) |
C3—N1—C2—C1 | −56.0 (3) | C5—C6—C7—C8 | 0.2 (3) |
S1—N1—C2—C1 | 176.94 (19) | N2—C6—C7—C8 | 179.9 (2) |
O1—C1—C2—N1 | 58.2 (3) | C6—C7—C8—C9 | −1.4 (3) |
C2—N1—C3—C4 | 56.1 (3) | C6—C7—C8—N3 | 178.42 (19) |
S1—N1—C3—C4 | −175.0 (2) | O4—N3—C8—C7 | −173.9 (2) |
C1—O1—C4—C3 | 60.1 (4) | O5—N3—C8—C7 | 5.3 (3) |
N1—C3—C4—O1 | −58.0 (4) | O4—N3—C8—C9 | 5.9 (4) |
N1—S1—C5—C6 | −177.40 (18) | O5—N3—C8—C9 | −174.9 (2) |
N1—S1—C5—C10 | 4.5 (2) | C7—C8—C9—C10 | 1.1 (4) |
C10—C5—C6—C7 | 1.2 (3) | N3—C8—C9—C10 | −178.7 (2) |
S1—C5—C6—C7 | −176.94 (17) | C8—C9—C10—C5 | 0.4 (4) |
C10—C5—C6—N2 | −178.5 (2) | C6—C5—C10—C9 | −1.5 (3) |
S1—C5—C6—N2 | 3.3 (3) | S1—C5—C10—C9 | 176.68 (19) |
O3—N2—C6—C7 | −3.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O5i | 0.97 | 2.54 | 3.224 (4) | 127 |
C9—H9···O3ii | 0.93 | 2.52 | 3.446 (4) | 174 |
C10—H10···N1 | 0.93 | 2.36 | 2.833 (3) | 111 |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H11N3O5S |
Mr | 285.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 6.4280 (2), 16.0850 (7), 12.1500 (6) |
β (°) | 97.4900 (16) |
V (Å3) | 1245.52 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.40 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.915, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7918, 2901, 2311 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.206, 1.12 |
No. of reflections | 2901 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.37 |
Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).
S1—N1 | 1.697 (2) | N2—C6 | 1.456 (3) |
S1—C5 | 1.755 (2) | N3—C8 | 1.462 (3) |
N1—S1—C5 | 100.41 (11) | C2—N1—S1 | 114.76 (19) |
C1—O1—C4 | 109.8 (2) | C3—N1—S1 | 111.44 (19) |
C2—N1—C3 | 110.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O5i | 0.97 | 2.54 | 3.224 (4) | 127 |
C9—H9···O3ii | 0.93 | 2.52 | 3.446 (4) | 174 |
C10—H10···N1 | 0.93 | 2.36 | 2.833 (3) | 111 |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z+1/2. |
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Sulfenamides are important compounds with versatile industrial applications. Bond polarization in sulfenamide derivatives, resulting from the difference in electronegativity between S and N, activates the S—N bond for attack by both nucleophiles and electrophiles and appears to be the factor primarily responsible for the chemistry of these compounds. The title compound, (I), is the result of the condensation reaction of 2,4-dinitrophenylsulfanylphalimide and morpholine. Its structure is decribed here as part of our work involving the study of the synthesis and structural characterization of divalent-sulfur compounds (Brito et al., 2004, 2005, 2006). A search of the Cambridge Structural Database (CSD, Version 5.27; Allen, 2002) for the morpholine fragment with an SII—X substituent (where X is alkyl, aryl or any adequate group) yielded only one example, viz 1,3-bis(2-methylphenyl)-2-(4-morpholino)isothiurea (CSD refcode TEHDAL; Sudha et al., 1996).
A view of the molecular structure of (I) is given in Fig. 1, and selected geometric parameters are listed in Table 1. The morpholine ring has a chair conformation [puckering amplitude QT = 0.573 (3) Å, θ = 180.0 (3)° and ϕ = 210 (25)° (Cremer & Pople, 1975)], with atoms N1 and O1 displaced by −0.659 (2) and 0.658 (2) Å, respectively, from the best plane through atoms C1, C2, C3 and C4 [maximum deviation ±0.0003 Å]. A survey of structures with morpholine rings shows wide variability, with the sum of the angles at the N atom ranging from 336 to 359° (Wong-Ng et al., 1982). In the present case, the sum of the angles at N1 is 336.7 (2)°.
The morpholine ring in (I) is oriented in such a way that the N1 lone pair can accept an intramolecular hydrogen bond from the C10—H10 group. To achieve this favourable intramolecular interaction, the N1—S1—C5—C10 torsion angle has a value of −4.5 (2)°, while the best planes of the 2,4-dinitrophenyl and morpholino groups are almost perpendicular to one another [dihedral angle 101.4 (2)°]. The average Csp3—Nsp3, Csp3—Csp3 and Csp3—Osp3 bond distances [1.474 (4), 1.449 (5) and 1.420 (4) Å, respectively] are comparable with the literature values (Allen et al., 1987).
The phenyl ring is slightly deformed, with atom C5 displaced out of the mean ring plane by 0.0095 (15) Å. The nitro groups in the ortho and para positions are rotated by 3.5 (4) and 6.1 (5)° from the aromatic ring, respectively. The C—S distance is shorter than the value of 1.777 (6) Å found in 4-[(dimethylamino)thio]-1,3-dinitrobenzene (Aupers et al.,1999) but longer than the value of 1.735 (4) Å found in 2-(2,4-dinitrophenylthioamino)-2,3,4,5-tetraphenyl-2H-pyrrole benzene solvate (Atkinson et al., 1985). The S—N distance is shorter than the normal S—N single-bond length (1.74 Å; Reference?), but is normal for this type of structure, many of which have S—N single bonds in the range 1.63–1.68 Å as a result of the π character of the S—N bond (Reference?).
The crystal structure of (I) is built up by an intramolecular C—H.·N hydrogen bond and two weak intermolecular C—H.·O hydrogen bonds. The intramolecular C10—H10···N interaction forms a five-membered closed S1/N1/C10/C5/H10 ring (Fig. 2). The molecules are linked into chains by two intermolecular C—H···O hydrogen bonds. Atoms C3 and C9 in the molecule at (x,y,z) acts as hydrogen-bond donors via atoms H3B and H9 to sulfenamide atoms O5 and O3 in the molecules at (x − 1,-y + 1/2,z + 1/2) and (x + 1,-y + 1/2, z + 1/2), so generating by translation two C(10) and C(7) (Bernstein et al., 1995) chains running parallel to the [100] direction (Fig. 3, Table 2). Such interactions involving the nitro O atoms are generally the dominant feature of the crystal structures of compounds containing nitroarenethiolate (O2NC6H4SX) fragments (Kucsman et al., 1984; Aupers et al., 1999; Low et al., 2000; Glidewell et al., 2000), as well as those of simple nitrobenzenes (Boonstra, 1963; Trotter & Williston, 1966; Choi & Abel, 1972; Herbstein & Kapon, 1990; Boese et al., 1992; Sekine et al., 1994).