Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016121/qb0136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016121/qb0136Isup2.hkl |
CCDC reference: 140866
Under an argon atmosphere, 2-nitrobenzenesulfonyl chloride (2.5 equivalents, 19.94 g, 0.09 mol) was added slowly to a stirred solution of DIEA (3 equivalents, 18.81 ml, 0.108 mol) and hydroxylamine hydrochloride (1 equivalents, 2.5 g, 0.036 mol) in dry acetonitrile (72 ml). The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo. The residue was diluted with dichloromethane, extracted with 5% NaOH, dried over MgSO4, and evaporated in vacuo. Solvent removal left a pale yellow semi-solid, which was dissolved in hot toluene and kept in a freezer overnight. The resulting pale-yellow crystals were filtered and washed with cold toluene. The yield was 22%.
H atoms were located in difference maps. For refinement, they were placed in calculated positions with C—H distance 0.95 Å and Biso = 1.3Beq for the bonded C atom, and thereafter treated as riding.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf-Nonius, 1994); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR (Burla et al., 1989); program(s) used to refine structure: LSFM in MolEN (Fair, 1990); software used to prepare material for publication: CIFGEN in MolEN (Fair, 1990).
C18H12N4O8S3 | F(000) = 1040 |
Mr = 508.51 | Dx = 1.619 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 7.670 (3) Å | θ = 10.5–18.1° |
b = 19.766 (5) Å | µ = 0.41 mm−1 |
c = 13.759 (3) Å | T = 100 K |
β = 90.63 (3)° | Prism, yellow |
V = 2085.8 (11) Å3 | 0.50 × 0.33 × 0.32 mm |
Z = 4 |
Enraf-Nonius CAD-4 (with Oxford Cryostream) diffractometer | 3426 reflections with I > 3σ(I) |
Radiation source: sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
θ/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −25→0 |
Tmin = 0.835, Tmax = 0.882 | l = −17→17 |
5118 measured reflections | 3 standard reflections every 60 min |
4775 independent reflections | intensity decay: 2.9% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.040 | w = 4Fo2/[σ2(Fo2) + 0.0004Fo4] |
S = 1.32 | (Δ/σ)max = 0.001 |
4775 reflections | Δρmax = 0.62 e Å−3 |
298 parameters | Δρmin = −0.37 e Å−3 |
C18H12N4O8S3 | V = 2085.8 (11) Å3 |
Mr = 508.51 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.670 (3) Å | µ = 0.41 mm−1 |
b = 19.766 (5) Å | T = 100 K |
c = 13.759 (3) Å | 0.50 × 0.33 × 0.32 mm |
β = 90.63 (3)° |
Enraf-Nonius CAD-4 (with Oxford Cryostream) diffractometer | 3426 reflections with I > 3σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.018 |
Tmin = 0.835, Tmax = 0.882 | 3 standard reflections every 60 min |
5118 measured reflections | intensity decay: 2.9% |
4775 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.040 | H-atom parameters constrained |
S = 1.32 | Δρmax = 0.62 e Å−3 |
4775 reflections | Δρmin = −0.37 e Å−3 |
298 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.66531 (7) | 0.29449 (3) | 0.70051 (4) | 0.0180 (2) | |
S2 | 0.54977 (7) | 0.42605 (3) | 0.77802 (4) | 0.0186 (2) | |
S3 | 0.64999 (7) | 0.40948 (3) | 0.56947 (4) | 0.0179 (2) | |
O1 | 0.8301 (2) | 0.28243 (8) | 0.6572 (1) | 0.0227 (8) | |
O2 | 0.6404 (2) | 0.28076 (8) | 0.8010 (1) | 0.0238 (8) | |
O3 | 0.2660 (2) | 0.20796 (9) | 0.8248 (1) | 0.0316 (9) | |
O4 | 0.2594 (2) | 0.31341 (8) | 0.7824 (1) | 0.0289 (9) | |
O5 | 0.5973 (2) | 0.60058 (8) | 0.9551 (1) | 0.0304 (9) | |
O6 | 0.4663 (2) | 0.51013 (8) | 0.9019 (1) | 0.0235 (8) | |
O7 | 0.5594 (2) | 0.41081 (9) | 0.2652 (1) | 0.0303 (9) | |
O8 | 0.7003 (2) | 0.44192 (8) | 0.3954 (1) | 0.0258 (8) | |
N1 | 0.6122 (2) | 0.37610 (9) | 0.6828 (1) | 0.0182 (9) | |
N2 | 0.2878 (2) | 0.2537 (1) | 0.7662 (1) | 0.0223 (9) | |
N3 | 0.5973 (2) | 0.5461 (1) | 0.9129 (1) | 0.0220 (9) | |
N4 | 0.5683 (2) | 0.41973 (9) | 0.3533 (1) | 0.0223 (9) | |
C1 | 0.5069 (3) | 0.2514 (1) | 0.6309 (1) | 0.016 (1) | |
C2 | 0.3425 (3) | 0.2349 (1) | 0.6668 (1) | 0.018 (1) | |
C3 | 0.2195 (3) | 0.2024 (1) | 0.6098 (2) | 0.020 (1) | |
C4 | 0.2586 (3) | 0.1880 (1) | 0.5139 (2) | 0.022 (1) | |
C5 | 0.4208 (3) | 0.2040 (1) | 0.4770 (1) | 0.020 (1) | |
C6 | 0.5455 (3) | 0.2349 (1) | 0.5354 (2) | 0.018 (1) | |
C7 | 0.7515 (3) | 0.4648 (1) | 0.8101 (1) | 0.018 (1) | |
C8 | 0.7571 (3) | 0.5207 (1) | 0.8719 (2) | 0.019 (1) | |
C9 | 0.9113 (3) | 0.5543 (1) | 0.8951 (2) | 0.025 (1) | |
C10 | 1.0635 (3) | 0.5324 (1) | 0.8561 (2) | 0.030 (1) | |
C11 | 1.0631 (3) | 0.4767 (1) | 0.7954 (2) | 0.028 (1) | |
C12 | 0.9106 (3) | 0.4431 (1) | 0.7724 (2) | 0.023 (1) | |
C13 | 0.4407 (3) | 0.4006 (1) | 0.5136 (2) | 0.017 (1) | |
C14 | 0.4195 (3) | 0.4045 (1) | 0.4126 (2) | 0.018 (1) | |
C15 | 0.2593 (3) | 0.3944 (1) | 0.3671 (2) | 0.026 (1) | |
C16 | 0.1151 (3) | 0.3814 (1) | 0.4217 (2) | 0.029 (1) | |
C17 | 0.1320 (3) | 0.3778 (1) | 0.5217 (2) | 0.027 (1) | |
C18 | 0.2921 (3) | 0.3873 (1) | 0.5671 (2) | 0.022 (1) | |
H3 | 0.1098 | 0.1900 | 0.6359 | 0.0267* | |
H4 | 0.1736 | 0.1671 | 0.4732 | 0.0289* | |
H5 | 0.4466 | 0.1937 | 0.4113 | 0.0268* | |
H6 | 0.6575 | 0.2447 | 0.5102 | 0.0236* | |
H9 | 0.9104 | 0.5921 | 0.9377 | 0.0331* | |
H10 | 1.1696 | 0.5552 | 0.8705 | 0.0421* | |
H11 | 1.1699 | 0.4612 | 0.7690 | 0.0401* | |
H12 | 0.9137 | 0.4048 | 0.7306 | 0.0302* | |
H15 | 0.2498 | 0.3965 | 0.2983 | 0.0340* | |
H16 | 0.0045 | 0.3750 | 0.3913 | 0.0389* | |
H17 | 0.0322 | 0.3687 | 0.5599 | 0.0362* | |
H18 | 0.3005 | 0.3846 | 0.6359 | 0.0283* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0167 (2) | 0.0188 (2) | 0.0185 (2) | −0.0015 (2) | −0.0045 (2) | 0.0007 (2) |
S2 | 0.0147 (2) | 0.0239 (3) | 0.0185 (2) | −0.0020 (2) | −0.0013 (2) | −0.0044 (2) |
S3 | 0.0159 (2) | 0.0199 (2) | 0.0180 (2) | −0.0027 (2) | −0.0013 (2) | 0.0002 (2) |
O1 | 0.0159 (7) | 0.0239 (8) | 0.0306 (8) | 0.0008 (7) | −0.0033 (6) | −0.0014 (7) |
O2 | 0.0278 (8) | 0.0264 (8) | 0.0183 (7) | −0.0038 (7) | −0.0073 (6) | 0.0027 (7) |
O3 | 0.047 (1) | 0.0309 (9) | 0.0215 (8) | −0.0100 (8) | 0.0045 (8) | 0.0072 (7) |
O4 | 0.0391 (9) | 0.0244 (8) | 0.0252 (8) | −0.0015 (8) | 0.0065 (7) | −0.0051 (7) |
O5 | 0.0319 (9) | 0.0255 (8) | 0.0345 (9) | 0.0042 (7) | −0.0008 (7) | −0.0117 (8) |
O6 | 0.0182 (7) | 0.0338 (9) | 0.0212 (7) | −0.0012 (7) | −0.0005 (6) | −0.0033 (7) |
O7 | 0.0366 (9) | 0.044 (1) | 0.0174 (7) | 0.0080 (9) | 0.0003 (7) | 0.0038 (8) |
O8 | 0.0223 (8) | 0.0288 (8) | 0.0267 (8) | −0.0049 (7) | 0.0011 (7) | 0.0049 (7) |
N1 | 0.0209 (9) | 0.0185 (9) | 0.0156 (8) | 0.0006 (8) | −0.0018 (7) | −0.0002 (7) |
N2 | 0.0206 (9) | 0.031 (1) | 0.0174 (9) | −0.0035 (9) | 0.0006 (7) | 0.0006 (8) |
N3 | 0.0211 (9) | 0.027 (1) | 0.0189 (9) | 0.0028 (8) | −0.0044 (7) | −0.0007 (8) |
N4 | 0.027 (1) | 0.0201 (9) | 0.0204 (9) | 0.0052 (8) | −0.0006 (8) | 0.0040 (8) |
C1 | 0.018 (1) | 0.0127 (9) | 0.018 (1) | −0.0006 (8) | −0.0054 (8) | 0.0021 (8) |
C2 | 0.023 (1) | 0.016 (1) | 0.0148 (9) | 0.0012 (9) | −0.0016 (8) | 0.0017 (9) |
C3 | 0.020 (1) | 0.019 (1) | 0.023 (1) | −0.0029 (9) | −0.0028 (9) | 0.0029 (9) |
C4 | 0.023 (1) | 0.021 (1) | 0.022 (1) | −0.0046 (9) | −0.0077 (9) | 0.0004 (9) |
C5 | 0.028 (1) | 0.019 (1) | 0.0144 (9) | 0.001 (1) | −0.0017 (9) | 0.0013 (9) |
C6 | 0.018 (1) | 0.015 (1) | 0.020 (1) | 0.0011 (9) | −0.0002 (9) | 0.0022 (9) |
C7 | 0.015 (1) | 0.019 (1) | 0.018 (1) | −0.0029 (9) | −0.0040 (8) | 0.0019 (9) |
C8 | 0.017 (1) | 0.020 (1) | 0.019 (1) | 0.0026 (9) | −0.0011 (8) | 0.0025 (9) |
C9 | 0.024 (1) | 0.020 (1) | 0.033 (1) | −0.001 (1) | −0.006 (1) | −0.006 (1) |
C10 | 0.019 (1) | 0.029 (1) | 0.049 (1) | −0.005 (1) | −0.006 (1) | −0.008 (1) |
C11 | 0.015 (1) | 0.033 (1) | 0.045 (1) | 0.001 (1) | 0.002 (1) | −0.008 (1) |
C12 | 0.020 (1) | 0.022 (1) | 0.027 (1) | −0.001 (1) | −0.0006 (9) | −0.007 (1) |
C13 | 0.019 (1) | 0.014 (1) | 0.019 (1) | 0.0010 (9) | −0.0036 (8) | 0.0002 (9) |
C14 | 0.020 (1) | 0.014 (1) | 0.021 (1) | 0.0028 (9) | −0.0013 (9) | 0.0013 (9) |
C15 | 0.031 (1) | 0.025 (1) | 0.022 (1) | 0.002 (1) | −0.007 (1) | 0.003 (1) |
C16 | 0.020 (1) | 0.033 (1) | 0.036 (1) | −0.001 (1) | −0.012 (1) | 0.004 (1) |
C17 | 0.017 (1) | 0.033 (1) | 0.033 (1) | 0.002 (1) | 0.001 (1) | 0.005 (1) |
C18 | 0.020 (1) | 0.025 (1) | 0.019 (1) | 0.003 (1) | −0.0005 (9) | 0.0018 (9) |
S1—O1 | 1.423 (2) | C5—C6 | 1.384 (3) |
S1—O2 | 1.424 (2) | C5—H5 | 0.95 |
S1—N1 | 1.681 (2) | C6—H6 | 0.95 |
S1—C1 | 1.758 (2) | C7—C8 | 1.395 (3) |
S2—N1 | 1.712 (2) | C7—C12 | 1.399 (3) |
S2—C7 | 1.777 (2) | C8—C9 | 1.391 (3) |
S3—N1 | 1.721 (2) | C9—C10 | 1.361 (3) |
S3—C13 | 1.781 (2) | C9—H9 | 0.95 |
O3—N2 | 1.224 (2) | C10—C11 | 1.382 (4) |
O4—N2 | 1.220 (3) | C10—H10 | 0.95 |
O5—N3 | 1.224 (2) | C11—C12 | 1.378 (3) |
O6—N3 | 1.239 (2) | C11—H11 | 0.95 |
O7—N4 | 1.225 (2) | C12—H12 | 0.95 |
O8—N4 | 1.241 (2) | C13—C14 | 1.399 (3) |
N2—C2 | 1.482 (3) | C13—C18 | 1.389 (3) |
N3—C8 | 1.445 (3) | C14—C15 | 1.387 (3) |
N4—C14 | 1.443 (3) | C15—C16 | 1.369 (3) |
C1—C2 | 1.397 (3) | C15—H15 | 0.95 |
C1—C6 | 1.389 (3) | C16—C17 | 1.382 (3) |
C2—C3 | 1.380 (3) | C16—H16 | 0.95 |
C3—C4 | 1.386 (3) | C17—C18 | 1.384 (3) |
C3—H3 | 0.95 | C17—H17 | 0.95 |
C4—C5 | 1.386 (3) | C18—H18 | 0.95 |
C4—H4 | 0.95 | ||
O1—S1—O2 | 120.26 (9) | C5—C6—H6 | 120.0 |
O1—S1—N1 | 108.37 (9) | S2—C7—C8 | 120.9 (2) |
O1—S1—C1 | 107.6 (1) | S2—C7—C12 | 122.4 (2) |
O2—S1—N1 | 106.76 (9) | C8—C7—C12 | 116.6 (2) |
O2—S1—C1 | 109.7 (1) | N3—C8—C7 | 119.6 (2) |
N1—S1—C1 | 102.74 (9) | N3—C8—C9 | 117.8 (2) |
N1—S2—C7 | 100.85 (9) | C7—C8—C9 | 122.6 (2) |
N1—S3—C13 | 101.14 (9) | C8—C9—C10 | 119.2 (2) |
S1—N1—S2 | 120.8 (1) | C8—C9—H9 | 120.4 |
S1—N1—S3 | 117.1 (1) | C10—C9—H9 | 120.4 |
S2—N1—S3 | 121.6 (1) | C9—C10—C11 | 119.7 (2) |
O3—N2—O4 | 124.6 (2) | C9—C10—H10 | 120.1 |
O3—N2—C2 | 117.7 (2) | C11—C10—H10 | 120.1 |
O4—N2—C2 | 117.6 (2) | C10—C11—C12 | 121.3 (2) |
O5—N3—O6 | 124.0 (2) | C10—C11—H11 | 119.4 |
O5—N3—C8 | 119.7 (2) | C12—C11—H11 | 119.4 |
O6—N3—C8 | 116.3 (2) | C7—C12—C11 | 120.5 (2) |
O7—N4—O8 | 123.3 (2) | C7—C12—H12 | 119.7 |
O7—N4—C14 | 119.6 (2) | C11—C12—H12 | 119.7 |
O8—N4—C14 | 117.1 (2) | S3—C13—C14 | 121.2 (2) |
S1—C1—C2 | 122.8 (2) | S3—C13—C18 | 122.1 (2) |
S1—C1—C6 | 118.4 (2) | C14—C13—C18 | 116.7 (2) |
C2—C1—C6 | 118.8 (2) | N4—C14—C13 | 119.3 (2) |
N2—C2—C1 | 122.2 (2) | N4—C14—C15 | 118.5 (2) |
N2—C2—C3 | 116.3 (2) | C13—C14—C15 | 122.2 (2) |
C1—C2—C3 | 121.5 (2) | C14—C15—C16 | 119.7 (2) |
C2—C3—C4 | 118.9 (2) | C14—C15—H15 | 120.1 |
C2—C3—H3 | 120.6 | C16—C15—H15 | 120.1 |
C4—C3—H3 | 120.6 | C15—C16—C17 | 119.3 (2) |
C3—C4—C5 | 120.4 (2) | C15—C16—H16 | 120.4 |
C3—C4—H4 | 119.8 | C17—C16—H16 | 120.4 |
C5—C4—H4 | 119.8 | C16—C17—C18 | 121.0 (2) |
C4—C5—C6 | 120.4 (2) | C16—C17—H17 | 119.5 |
C4—C5—H5 | 119.8 | C18—C17—H17 | 119.5 |
C6—C5—H5 | 119.8 | C13—C18—C17 | 121.1 (2) |
C1—C6—C5 | 120.0 (2) | C13—C18—H18 | 119.5 |
C1—C6—H6 | 120.0 | C17—C18—H18 | 119.5 |
O1—S1—N1—S2 | −128.9 (1) | S1—C1—C2—C3 | 178.6 (2) |
O1—S1—N1—S3 | 42.9 (1) | C6—C1—C2—N2 | −177.0 (2) |
O2—S1—N1—S2 | 1.9 (1) | C6—C1—C2—C3 | 0.4 (3) |
O2—S1—N1—S3 | 173.8 (1) | S1—C1—C6—C5 | −176.8 (2) |
C1—S1—N1—S2 | 117.4 (1) | C2—C1—C6—C5 | 1.5 (3) |
C1—S1—N1—S3 | −70.8 (1) | N2—C2—C3—C4 | 175.3 (2) |
O1—S1—C1—C2 | 160.1 (2) | C1—C2—C3—C4 | −2.3 (3) |
O1—S1—C1—C6 | −21.7 (2) | C2—C3—C4—C5 | 2.2 (3) |
O2—S1—C1—C2 | 27.6 (2) | C3—C4—C5—C6 | −0.4 (3) |
O2—S1—C1—C6 | −154.2 (2) | C4—C5—C6—C1 | −1.5 (3) |
N1—S1—C1—C2 | −85.6 (2) | S2—C7—C8—N3 | 2.1 (3) |
N1—S1—C1—C6 | 92.6 (2) | S2—C7—C8—C9 | −176.9 (2) |
C7—S2—N1—S1 | 94.9 (1) | C12—C7—C8—N3 | 179.6 (2) |
C7—S2—N1—S3 | −76.6 (1) | C12—C7—C8—C9 | 0.6 (3) |
N1—S2—C7—C8 | 166.4 (2) | S2—C7—C12—C11 | 176.7 (2) |
N1—S2—C7—C12 | −10.9 (2) | C8—C7—C12—C11 | −0.7 (3) |
C13—S3—N1—S1 | 96.3 (1) | N3—C8—C9—C10 | −178.8 (2) |
C13—S3—N1—S2 | −91.9 (1) | C7—C8—C9—C10 | 0.3 (3) |
N1—S3—C13—C14 | −162.7 (2) | C8—C9—C10—C11 | −0.9 (4) |
N1—S3—C13—C18 | 14.9 (2) | C9—C10—C11—C12 | 0.8 (4) |
O3—N2—C2—C1 | −112.6 (2) | C10—C11—C12—C7 | 0.1 (4) |
O3—N2—C2—C3 | 69.8 (3) | S3—C13—C14—N4 | −3.6 (3) |
O4—N2—C2—C1 | 70.9 (3) | S3—C13—C14—C15 | 176.7 (2) |
O4—N2—C2—C3 | −106.6 (2) | C18—C13—C14—N4 | 178.6 (2) |
O5—N3—C8—C7 | −169.2 (2) | C18—C13—C14—C15 | −1.0 (3) |
O5—N3—C8—C9 | 9.8 (3) | S3—C13—C18—C17 | −177.3 (2) |
O6—N3—C8—C7 | 10.4 (3) | C14—C13—C18—C17 | 0.5 (3) |
O6—N3—C8—C9 | −170.6 (2) | N4—C14—C15—C16 | −178.5 (2) |
O7—N4—C14—C13 | 166.4 (2) | C13—C14—C15—C16 | 1.2 (3) |
O7—N4—C14—C15 | −14.0 (3) | C14—C15—C16—C17 | −0.7 (4) |
O8—N4—C14—C13 | −14.0 (3) | C15—C16—C17—C18 | 0.1 (4) |
O8—N4—C14—C15 | 165.7 (2) | C16—C17—C18—C13 | −0.0 (5) |
S1—C1—C2—N2 | 1.2 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H12N4O8S3 |
Mr | 508.51 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 7.670 (3), 19.766 (5), 13.759 (3) |
β (°) | 90.63 (3) |
V (Å3) | 2085.8 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.50 × 0.33 × 0.32 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 (with Oxford Cryostream) diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.835, 0.882 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 5118, 4775, 3426 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.040, 1.32 |
No. of reflections | 4775 |
No. of parameters | 298 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.62, −0.37 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), SIR (Burla et al., 1989), LSFM in MolEN (Fair, 1990), CIFGEN in MolEN (Fair, 1990).
The aim of the study was to synthesize O,N-bis(2-nitrobenzenesulfonyl)hydroxylamine, which could deliver its protected amino group to various nucleophiles via electrophilic amination. This is important in the synthesis of α-hyrazino acids for the synthesis of hydrazino peptides. When N,N-diisopropylethylamine, (DIEA) was used as a base in the reaction, the main product was the title compound. When collidine was used in place of DIEA, the desired product was obtained without formation of the title compound·We thus believe that the DIEA is acting as a reducing agent in the formation of the title compound.
The central N atom is essentially planar, lying 0.071 (2) Å out of the plane defined by the three S atoms. Tris(thiophenyl)amine (Carruthers et al., 1981) also has a near planar central N atom. N—S distances to thiol S are 1.712 (2) and 1.721 (2) Å, while the N1—S1 distance is shorter, 1.681 (2) Å. The nitro group on phenyl ring C1 through C6 lies out of plane, with C3—C2—N2—O3 torsion angle 69.8 (3)°. The other two nitro groups are nearer coplanarity with their respective phenyl rings, with torsion angles O6—N3—C8—C7 10.4 (3) and O8—N4—C14—C13 − 14.0 (3)°.
Short intermolecular contacts exist between nitro groups of inversion-related molecules. O6 has distances of 2.772 (2) Å to O6i and 2.827 (2) Å to N3i [symmetry code: (i) 1 − x, 1 − y, 2 − z], as well as a distance of 2.785 (2) Å to O7ii [symmetry code: (ii) 1 − x, 1 − y, 1 − z]. An N3···O7ii contact of distance 2.848 (2) Å also exists.