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The title mol­ecule, C13H10N2O7S, is stabilized by weak intermolecular C—H...O interactions. The dihedral angle between the mean planes of the 4-tolyl and 2,4-di­nitro­phenyl rings is 19.26 (3)°. Both O atoms of the 4-nitro group form a `fork-like' intermolecular hydrogen-bonding motif with the C—H groups of the aromatic rings. In addition, one of the O atoms of the 2-nitro group and one of the O atoms of the sulfonyl group are also involved in weak intermolecular hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004197/lh6038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004197/lh6038Isup2.hkl
Contains datablock I

CCDC reference: 206800

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.087
  • Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

2,4-dinitrophenyl 4-toluenesulfonate top
Crystal data top
C13H10N2O7SDx = 1.634 Mg m3
Mr = 338.29Melting point = 119–121 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8997 reflections
a = 13.3935 (7) Åθ = 2.5–27.5°
b = 13.4828 (8) ŵ = 0.28 mm1
c = 15.2291 (8) ÅT = 100 K
V = 2750.1 (3) Å3Plate, colorless
Z = 80.40 × 0.30 × 0.07 mm
F(000) = 1392
Data collection top
Bruker SMART CCD area-detector
diffractometer
3170 independent reflections
Radiation source: fine-focus sealed tube2867 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)
h = 1717
Tmin = 0.897, Tmax = 0.981k = 1717
31334 measured reflectionsl = 1919
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0531P)2 + 1.1269P]
where P = (Fo2 + 2Fc2)/3
3170 reflections(Δ/σ)max = 0.001
248 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.29 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.45137 (2)0.18709 (2)0.592919 (19)0.01305 (10)
O10.50212 (7)0.17897 (7)0.67450 (6)0.0204 (2)
O20.45800 (7)0.27661 (7)0.54357 (6)0.0190 (2)
O30.49147 (6)0.09791 (6)0.53102 (6)0.01485 (19)
O40.65747 (7)0.01324 (7)0.60320 (6)0.0195 (2)
O50.77963 (7)0.11669 (9)0.58437 (6)0.0272 (2)
O60.84702 (7)0.15067 (8)0.26858 (7)0.0246 (2)
O70.72232 (9)0.17391 (9)0.18095 (6)0.0309 (3)
N10.70164 (8)0.07684 (8)0.56151 (7)0.0152 (2)
N20.75767 (9)0.15729 (8)0.25340 (7)0.0195 (2)
C10.02328 (11)0.05642 (13)0.62561 (11)0.0250 (3)
C20.12992 (9)0.09011 (9)0.61783 (8)0.0160 (3)
C30.19217 (10)0.09016 (9)0.69109 (8)0.0158 (2)
C40.29185 (9)0.11779 (9)0.68452 (8)0.0144 (2)
C50.32771 (9)0.14782 (9)0.60331 (8)0.0126 (2)
C60.26692 (9)0.15075 (9)0.52920 (8)0.0140 (2)
C70.16838 (9)0.12091 (10)0.53703 (8)0.0154 (2)
C80.55817 (9)0.11742 (9)0.46365 (8)0.0129 (2)
C90.66054 (9)0.10640 (9)0.47624 (7)0.0126 (2)
C100.72717 (9)0.12149 (9)0.40843 (8)0.0139 (2)
C110.68829 (10)0.14494 (9)0.32733 (8)0.0150 (2)
C120.58680 (10)0.15706 (9)0.31256 (8)0.0174 (3)
C130.52172 (10)0.14405 (10)0.38202 (8)0.0165 (3)
H1A0.020 (2)0.085 (2)0.5896 (17)0.069 (8)*
H1B0.0017 (18)0.0535 (18)0.6819 (16)0.058 (7)*
H1C0.0208 (16)0.0149 (18)0.6092 (14)0.050 (6)*
H30.1657 (13)0.0692 (13)0.7475 (12)0.028 (4)*
H40.3366 (13)0.1161 (13)0.7335 (12)0.026 (4)*
H60.2916 (12)0.1708 (11)0.4750 (11)0.017 (4)*
H70.1265 (12)0.1225 (12)0.4864 (11)0.020 (4)*
H100.7939 (13)0.1146 (12)0.4191 (11)0.021 (4)*
H120.5649 (12)0.1761 (12)0.2570 (12)0.020 (4)*
H130.4521 (12)0.1510 (12)0.3718 (10)0.017 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01094 (16)0.01450 (17)0.01372 (16)0.00064 (10)0.00048 (10)0.00202 (10)
O10.0157 (4)0.0275 (5)0.0179 (5)0.0011 (4)0.0040 (4)0.0048 (4)
O20.0168 (4)0.0154 (5)0.0249 (5)0.0005 (3)0.0047 (4)0.0004 (4)
O30.0144 (4)0.0139 (4)0.0163 (4)0.0007 (3)0.0055 (3)0.0008 (3)
O40.0256 (5)0.0196 (5)0.0135 (4)0.0004 (4)0.0011 (3)0.0034 (3)
O50.0181 (5)0.0433 (6)0.0201 (5)0.0064 (4)0.0072 (4)0.0017 (4)
O60.0219 (5)0.0283 (5)0.0236 (5)0.0045 (4)0.0104 (4)0.0039 (4)
O70.0414 (6)0.0391 (6)0.0123 (5)0.0063 (5)0.0068 (4)0.0045 (4)
N10.0142 (5)0.0198 (5)0.0116 (5)0.0027 (4)0.0002 (4)0.0014 (4)
N20.0278 (6)0.0154 (5)0.0154 (5)0.0016 (4)0.0076 (4)0.0018 (4)
C10.0160 (6)0.0333 (8)0.0257 (7)0.0049 (6)0.0021 (6)0.0002 (6)
C20.0140 (6)0.0150 (6)0.0190 (6)0.0013 (4)0.0019 (5)0.0020 (5)
C30.0180 (6)0.0166 (6)0.0128 (5)0.0005 (5)0.0043 (4)0.0000 (4)
C40.0159 (6)0.0151 (6)0.0121 (6)0.0018 (4)0.0013 (4)0.0006 (4)
C50.0103 (5)0.0127 (6)0.0147 (5)0.0001 (4)0.0012 (4)0.0017 (4)
C60.0160 (6)0.0145 (6)0.0115 (5)0.0015 (4)0.0018 (4)0.0004 (4)
C70.0143 (6)0.0171 (6)0.0147 (6)0.0018 (5)0.0025 (4)0.0017 (4)
C80.0135 (6)0.0124 (5)0.0128 (5)0.0014 (4)0.0023 (4)0.0010 (4)
C90.0148 (6)0.0118 (5)0.0112 (5)0.0001 (4)0.0015 (4)0.0008 (4)
C100.0125 (6)0.0131 (6)0.0160 (6)0.0007 (4)0.0016 (4)0.0023 (4)
C110.0192 (6)0.0130 (6)0.0130 (5)0.0014 (4)0.0050 (5)0.0010 (4)
C120.0221 (7)0.0168 (6)0.0132 (6)0.0006 (5)0.0032 (5)0.0013 (4)
C130.0144 (6)0.0172 (6)0.0179 (6)0.0004 (5)0.0027 (5)0.0005 (5)
Geometric parameters (Å, º) top
S—O11.4204 (10)C3—C41.3897 (18)
S—O21.4246 (10)C3—H30.972 (18)
S—O31.6195 (9)C4—C51.3871 (17)
S—C51.7460 (12)C4—H40.958 (18)
O3—C81.3855 (14)C5—C61.3922 (17)
O4—N11.2201 (14)C6—C71.3848 (18)
O5—N11.2251 (15)C6—H60.929 (16)
O6—N21.2220 (16)C7—H70.954 (16)
O7—N21.2214 (16)C8—C131.3830 (17)
N1—C91.4656 (15)C8—C91.3924 (16)
N2—C111.4693 (16)C9—C101.3800 (17)
C1—C21.5035 (18)C10—C111.3771 (17)
C1—H1A0.88 (3)C10—H100.913 (17)
C1—H1B0.90 (2)C11—C121.3875 (19)
C1—H1C0.99 (2)C12—C131.3819 (18)
C2—C31.3927 (18)C12—H120.932 (18)
C2—C71.3972 (17)C13—H130.950 (16)
O1—S—O2119.79 (6)C4—C5—C6121.91 (11)
O1—S—O3107.05 (5)C4—C5—S119.85 (9)
O2—S—O3107.54 (5)C6—C5—S118.21 (9)
O1—S—C5110.57 (6)C7—C6—C5118.64 (11)
O2—S—C5111.34 (6)C7—C6—H6120.0 (10)
O3—S—C598.17 (5)C5—C6—H6121.3 (10)
C8—O3—S120.25 (8)C6—C7—C2120.90 (11)
O4—N1—O5125.01 (11)C6—C7—H7119.0 (10)
O4—N1—C9118.04 (10)C2—C7—H7120.1 (10)
O5—N1—C9116.92 (10)C13—C8—O3119.17 (11)
O7—N2—O6124.33 (12)C13—C8—C9119.94 (11)
O7—N2—C11117.89 (12)O3—C8—C9120.84 (11)
O6—N2—C11117.78 (11)C10—C9—C8121.20 (11)
C2—C1—H1A115.9 (17)C10—C9—N1117.40 (10)
C2—C1—H1B113.0 (16)C8—C9—N1121.39 (10)
H1A—C1—H1B114 (2)C11—C10—C9117.42 (11)
C2—C1—H1C107.7 (13)C11—C10—H10123.6 (10)
H1A—C1—H1C104 (2)C9—C10—H10119.0 (10)
H1B—C1—H1C100.7 (19)C10—C11—C12122.88 (11)
C3—C2—C7118.99 (11)C10—C11—N2118.31 (11)
C3—C2—C1120.38 (12)C12—C11—N2118.81 (11)
C7—C2—C1120.63 (12)C13—C12—C11118.61 (11)
C4—C3—C2121.17 (11)C13—C12—H12122.2 (10)
C4—C3—H3119.5 (10)C11—C12—H12119.2 (10)
C2—C3—H3119.3 (11)C12—C13—C8119.90 (12)
C5—C4—C3118.36 (11)C12—C13—H13118.8 (10)
C5—C4—H4119.0 (10)C8—C13—H13121.3 (10)
C3—C4—H4122.7 (10)
O1—S—O3—C8104.44 (9)C13—C8—C9—C100.07 (19)
O2—S—O3—C825.49 (10)O3—C8—C9—C10177.14 (11)
C5—S—O3—C8141.02 (9)C13—C8—C9—N1179.09 (11)
C7—C2—C3—C41.65 (19)O3—C8—C9—N11.88 (18)
C1—C2—C3—C4177.76 (13)O4—N1—C9—C10138.89 (12)
C2—C3—C4—C51.54 (19)O5—N1—C9—C1039.39 (16)
C3—C4—C5—C60.07 (19)O4—N1—C9—C840.17 (16)
C3—C4—C5—S177.87 (9)O5—N1—C9—C8141.55 (12)
O1—S—C5—C42.05 (12)C8—C9—C10—C111.89 (18)
O2—S—C5—C4133.69 (10)N1—C9—C10—C11177.17 (11)
O3—S—C5—C4113.79 (10)C9—C10—C11—C122.29 (19)
O1—S—C5—C6179.93 (9)C9—C10—C11—N2177.53 (11)
O2—S—C5—C644.32 (11)O7—N2—C11—C10176.94 (12)
O3—S—C5—C668.20 (10)O6—N2—C11—C103.36 (17)
C4—C5—C6—C71.25 (18)O7—N2—C11—C122.88 (17)
S—C5—C6—C7179.22 (9)O6—N2—C11—C12176.82 (11)
C5—C6—C7—C21.14 (19)C10—C11—C12—C130.68 (19)
C3—C2—C7—C60.28 (19)N2—C11—C12—C13179.14 (11)
C1—C2—C7—C6179.13 (12)C11—C12—C13—C81.38 (19)
S—O3—C8—C1387.56 (13)O3—C8—C13—C12175.52 (11)
S—O3—C8—C995.21 (12)C9—C8—C13—C121.74 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O4i0.950 (16)2.683 (16)3.2107 (16)115.7 (12)
C13—H13···O6ii0.950 (16)2.560 (16)3.2777 (16)132.5 (12)
C12—H12···O1iii0.932 (18)2.470 (17)3.2549 (16)141.9 (13)
C10—H10···O2iv0.913 (17)2.703 (17)3.4612 (15)141.1 (14)
C6—H6···O7ii0.929 (16)2.551 (16)3.2706 (16)134.6 (12)
C6—H6···O4i0.929 (16)2.835 (15)3.1592 (15)101.8 (11)
C7—H7···O2v0.954 (16)2.674 (16)3.3698 (15)130.2 (12)
C7—H7···O7ii0.954 (16)2.937 (16)3.4716 (16)116.7 (11)
C3—H3···O4vi0.971 (18)2.398 (18)3.3325 (15)161.2 (14)
C3—H3···O1vi0.971 (18)2.899 (18)3.4789 (15)119.3 (12)
C3—H3···O6i0.971 (18)2.979 (17)3.3460 (16)103.8 (11)
C4—H4···O5vi0.958 (18)2.876 (17)3.5234 (15)125.8 (13)
C1—H1A···O2v0.88 (3)2.77 (3)3.531 (2)145 (2)
C1—H1B···O1vi0.90 (2)2.77 (2)3.4752 (19)136 (2)
C1—H1A···O5vii0.88 (3)2.72 (3)3.4211 (18)137 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x1/2, y, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1/2, y+1/2, z+1; (v) x1/2, y+1/2, z+1; (vi) x1/2, y, z+3/2; (vii) x1, y, z.
 

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