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The N atoms of the title compound, C18H16N2O4S2, are not preorganized for metal cation binding. The N-H groups form hydrogen bonds with symmetry-equivalent sulfonamide groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001133/lh6351sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001133/lh6351Isup2.hkl
Contains datablock I

CCDC reference: 264059

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • R factor = 0.033
  • wR factor = 0.090
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

N,N'-(o-Phenylene)dibenzenesulfonamide top
Crystal data top
C18H16N2O4S2F(000) = 808
Mr = 388.4Dx = 1.480 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.5311 (8) Åθ = 10.1–16.0°
b = 12.5662 (10) ŵ = 0.33 mm1
c = 14.9862 (12) ÅT = 200 K
β = 103.774 (7)°Prism, colorless
V = 1743.3 (3) Å30.44 × 0.34 × 0.29 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.036
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.1°
Graphite monochromatorh = 120
ω scansk = 1616
8691 measured reflectionsl = 1919
4198 independent reflections3 standard reflections every 120 min
3371 reflections with I > 2σ(I) intensity decay: 4%
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0402P)2 + 0.6951P]
where P = (Fo2 + 2Fc2)/3
4198 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.41 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S10.66159 (4)0.60337 (3)0.10487 (2)0.0217 (1)
S21.04688 (4)0.64797 (3)0.07323 (3)0.0228 (1)
O10.80779 (12)0.63132 (10)0.14659 (8)0.0279 (3)
O20.61142 (13)0.49634 (9)0.11226 (8)0.0283 (3)
O31.12350 (12)0.56226 (9)0.01979 (8)0.0271 (3)
O41.12072 (13)0.74595 (10)0.07854 (9)0.0330 (4)
N10.63487 (15)0.62474 (11)0.00570 (9)0.0234 (4)
N20.91067 (15)0.66955 (11)0.02699 (9)0.0245 (4)
C10.66442 (17)0.72736 (13)0.03928 (10)0.0241 (4)
C20.80122 (17)0.74722 (12)0.05488 (10)0.0232 (4)
C30.8259 (2)0.84392 (14)0.09395 (12)0.0315 (5)
C40.7165 (2)0.91867 (15)0.11609 (14)0.0404 (6)
C50.5823 (2)0.89981 (16)0.09964 (14)0.0406 (6)
C60.5565 (2)0.80379 (15)0.06104 (12)0.0334 (5)
C110.54795 (16)0.69011 (12)0.14763 (10)0.0222 (4)
C120.40034 (18)0.66971 (14)0.12630 (12)0.0301 (5)
C130.31151 (18)0.73612 (15)0.16140 (13)0.0333 (5)
C140.36831 (19)0.82084 (14)0.21738 (11)0.0296 (5)
C150.51551 (19)0.84185 (14)0.23657 (11)0.0296 (5)
C160.60647 (17)0.77651 (13)0.20126 (11)0.0268 (4)
C210.97546 (16)0.60210 (13)0.18574 (10)0.0244 (4)
C220.8956 (2)0.50840 (14)0.19887 (12)0.0329 (5)
C230.8440 (2)0.47056 (16)0.28737 (13)0.0398 (6)
C240.8734 (2)0.52557 (18)0.36138 (12)0.0412 (6)
C250.9516 (2)0.61843 (18)0.34747 (12)0.0405 (6)
C261.00271 (18)0.65828 (15)0.25934 (12)0.0311 (5)
H10.562 (2)0.5984 (17)0.0328 (14)0.0350*
H20.887 (2)0.6162 (15)0.0034 (14)0.0370*
H30.917900.858500.105400.0380*
H40.734200.984200.143100.0480*
H50.508500.952100.114600.0490*
H60.464400.790200.049400.0400*
H120.361400.611200.088300.0360*
H130.210300.723600.147000.0400*
H140.306500.864700.242800.0360*
H150.553900.901000.273900.0360*
H160.707200.790700.213600.0320*
H220.876800.470900.147900.0390*
H230.788500.407000.297600.0480*
H240.839100.498800.421900.0490*
H250.970800.655600.398500.0490*
H261.055600.723100.249600.0370*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0195 (2)0.0231 (2)0.0234 (2)0.0007 (1)0.0067 (1)0.0014 (1)
S20.0202 (2)0.0253 (2)0.0239 (2)0.0011 (1)0.0073 (1)0.0029 (1)
O10.0193 (5)0.0351 (6)0.0291 (6)0.0007 (5)0.0052 (4)0.0006 (5)
O20.0296 (6)0.0237 (6)0.0328 (6)0.0006 (5)0.0097 (5)0.0033 (5)
O30.0210 (5)0.0311 (6)0.0288 (6)0.0026 (5)0.0053 (4)0.0051 (5)
O40.0306 (6)0.0311 (6)0.0385 (7)0.0084 (5)0.0107 (5)0.0036 (5)
N10.0217 (6)0.0259 (7)0.0224 (6)0.0018 (5)0.0051 (5)0.0001 (5)
N20.0267 (7)0.0237 (7)0.0265 (7)0.0035 (5)0.0129 (5)0.0058 (5)
C10.0283 (8)0.0237 (7)0.0199 (7)0.0028 (6)0.0050 (6)0.0006 (6)
C20.0278 (7)0.0228 (7)0.0194 (7)0.0018 (6)0.0064 (6)0.0002 (6)
C30.0352 (9)0.0281 (9)0.0327 (8)0.0004 (7)0.0109 (7)0.0060 (7)
C40.0525 (12)0.0271 (9)0.0422 (10)0.0060 (8)0.0127 (9)0.0114 (8)
C50.0436 (11)0.0333 (9)0.0437 (10)0.0160 (9)0.0081 (8)0.0096 (8)
C60.0309 (9)0.0346 (9)0.0347 (9)0.0087 (7)0.0081 (7)0.0041 (7)
C110.0210 (7)0.0249 (7)0.0220 (7)0.0009 (6)0.0078 (6)0.0011 (6)
C120.0237 (8)0.0320 (9)0.0347 (9)0.0032 (7)0.0072 (7)0.0073 (7)
C130.0210 (7)0.0385 (10)0.0413 (9)0.0010 (7)0.0095 (7)0.0037 (8)
C140.0314 (8)0.0294 (8)0.0308 (8)0.0055 (7)0.0127 (7)0.0014 (7)
C150.0345 (9)0.0273 (8)0.0282 (8)0.0008 (7)0.0098 (7)0.0037 (6)
C160.0235 (7)0.0304 (8)0.0269 (8)0.0038 (6)0.0067 (6)0.0011 (6)
C210.0194 (7)0.0306 (8)0.0237 (7)0.0050 (6)0.0064 (6)0.0029 (6)
C220.0386 (10)0.0304 (9)0.0284 (8)0.0003 (7)0.0057 (7)0.0049 (7)
C230.0451 (11)0.0340 (9)0.0356 (10)0.0008 (8)0.0004 (8)0.0028 (8)
C240.0413 (10)0.0534 (12)0.0259 (8)0.0139 (9)0.0023 (7)0.0032 (8)
C250.0372 (10)0.0600 (13)0.0260 (8)0.0069 (9)0.0108 (7)0.0093 (8)
C260.0247 (8)0.0400 (10)0.0311 (8)0.0016 (7)0.0114 (6)0.0078 (7)
Geometric parameters (Å, º) top
S1—O11.4287 (12)C14—C151.389 (3)
S1—O21.4405 (12)C15—C161.387 (2)
S1—N11.6376 (14)C21—C261.385 (2)
S1—C111.7614 (16)C21—C221.390 (2)
S2—O31.4340 (12)C22—C231.384 (3)
S2—O41.4298 (13)C23—C241.391 (3)
S2—N21.6333 (15)C24—C251.374 (3)
S2—C211.7584 (15)C25—C261.388 (3)
N1—C11.436 (2)C3—H30.9506
N2—C21.417 (2)C4—H40.9502
N1—H10.79 (2)C5—H50.9496
N2—H20.814 (19)C6—H60.9503
C1—C21.401 (2)C12—H120.9497
C1—C61.388 (3)C13—H130.9501
C2—C31.393 (2)C14—H140.9502
C3—C41.384 (3)C15—H150.9497
C4—C51.380 (3)C16—H160.9504
C5—C61.385 (3)C22—H220.9502
C11—C161.387 (2)C23—H230.9501
C11—C121.390 (2)C24—H240.9494
C12—C131.379 (3)C25—H250.9503
C13—C141.384 (3)C26—H260.9507
S1···N23.5308 (15)C25···C2vi3.528 (2)
S1···O3i3.3759 (12)C26···C14x3.593 (3)
S1···H22.99 (2)C26···O1vi3.344 (2)
S2···H32.9087C2···H25ii2.7914
O1···N23.0288 (18)C3···H25ii2.9258
O1···C23.3393 (19)C4···H24ii3.0481
O1···C26ii3.344 (2)C13···H26ix3.0887
O1···C22i3.261 (2)C13···H23iv3.0390
O2···C15iii3.416 (2)C14···H4xi2.7709
O2···C14iii3.344 (2)C21···H16vi2.9650
O2···N1iv2.9310 (19)C24···H3xii3.0139
O3···N1i3.2485 (19)C25···H16vi2.9296
O3···C12v3.291 (2)C26···H13x3.0676
O3···S1i3.3759 (12)C26···H14x2.9024
O3···O3i3.0012 (17)C26···H16vi2.8221
O3···N2i3.0318 (18)H1···H62.5741
O4···C33.026 (2)H1···O2iv2.15 (2)
O1···H22.54 (2)H2···S12.99 (2)
O1···H162.5293H2···O12.54 (2)
O2···H122.7356H2···N12.40 (2)
O2···H15iii2.8476H2···O3i2.275 (19)
O2···H14iii2.6939H3···S22.9087
O2···H1iv2.15 (2)H3···O42.3513
O3···H12v2.5287H3···C24xiii3.0139
O3···H2i2.275 (19)H4···C14xi2.7709
O3···H22i2.5480H4···H14xi2.3900
O3···H222.8953H6···H12.5741
O4···H32.3513H12···O22.7356
O4···H262.5063H12···O3vii2.5287
N1···N22.780 (2)H13···H22iv2.5823
N1···O2iv2.9310 (19)H13···C26ix3.0676
N1···O3i3.2485 (19)H13···H26ix2.4722
N2···S13.5308 (15)H14···O2viii2.6939
N2···O3i3.0318 (18)H14···H4xi2.3900
N2···O13.0288 (18)H14···C26ix2.9024
N2···N12.780 (2)H15···O2viii2.8476
N1···H22.40 (2)H16···O12.5293
N2···H25ii2.8876H16···C21ii2.9649
C1···C15vi3.433 (2)H16···C25ii2.9296
C2···O13.3393 (19)H16···C26ii2.8221
C2···C25ii3.528 (2)H22···O32.8953
C3···O43.026 (2)H22···O3i2.5480
C6···C15vi3.484 (2)H22···H13iv2.5823
C6···C113.457 (2)H23···C13iv3.0390
C11···C63.457 (2)H24···C4vi3.0481
C12···O3vii3.291 (2)H25···N2vi2.8876
C14···O2viii3.344 (2)H25···C2vi2.7914
C14···C26ix3.593 (3)H25···C3vi2.9258
C15···C1ii3.433 (2)H26···O42.5063
C15···C6ii3.484 (2)H26···C13x3.0887
C15···O2viii3.416 (2)H26···H13x2.4722
C22···O1i3.261 (2)
O1—S1—O2120.19 (7)S2—C21—C22119.16 (12)
O1—S1—N1107.64 (7)S2—C21—C26119.56 (13)
O1—S1—C11107.99 (7)C22—C21—C26121.27 (15)
O2—S1—N1104.86 (7)C21—C22—C23118.95 (16)
O2—S1—C11107.80 (7)C22—C23—C24120.01 (18)
N1—S1—C11107.80 (7)C23—C24—C25120.42 (17)
O3—S2—O4119.07 (8)C24—C25—C26120.39 (17)
O3—S2—N2103.79 (7)C21—C26—C25118.95 (17)
O3—S2—C21108.59 (7)C2—C3—H3119.96
O4—S2—N2109.40 (7)C4—C3—H3120.05
O4—S2—C21108.19 (8)C3—C4—H4119.36
N2—S2—C21107.21 (7)C5—C4—H4119.42
S1—N1—C1120.37 (11)C4—C5—H5120.34
S2—N2—C2126.37 (11)C6—C5—H5120.41
S1—N1—H1111.0 (15)C1—C6—H6119.85
C1—N1—H1114.7 (15)C5—C6—H6119.79
C2—N2—H2115.8 (14)C11—C12—H12120.68
S2—N2—H2112.2 (14)C13—C12—H12120.62
N1—C1—C6120.49 (15)C12—C13—H13119.70
C2—C1—C6120.31 (15)C14—C13—H13119.65
N1—C1—C2119.10 (14)C13—C14—H14119.94
N2—C2—C1118.50 (14)C15—C14—H14119.93
N2—C2—C3122.60 (15)C14—C15—H15119.96
C1—C2—C3118.86 (15)C16—C15—H15119.99
C2—C3—C4120.00 (17)C11—C16—H16120.53
C3—C4—C5121.22 (18)C15—C16—H16120.59
C4—C5—C6119.25 (18)C21—C22—H22120.52
C1—C6—C5120.36 (18)C23—C22—H22120.52
S1—C11—C12118.59 (12)C22—C23—H23120.03
S1—C11—C16119.88 (12)C24—C23—H23119.95
C12—C11—C16121.54 (15)C23—C24—H24119.78
C11—C12—C13118.70 (16)C25—C24—H24119.80
C12—C13—C14120.65 (17)C24—C25—H25119.80
C13—C14—C15120.14 (16)C26—C25—H25119.82
C14—C15—C16120.05 (16)C21—C26—H26120.50
C11—C16—C15118.88 (15)C25—C26—H26120.56
O1—S1—N1—C154.90 (14)C2—C1—C6—C51.0 (3)
O2—S1—N1—C1176.02 (13)N1—C1—C6—C5175.31 (16)
C11—S1—N1—C161.36 (14)C6—C1—C2—C31.1 (2)
O1—S1—C11—C12171.64 (13)N2—C2—C3—C4177.12 (16)
O1—S1—C11—C168.40 (15)C1—C2—C3—C40.4 (2)
O2—S1—C11—C1240.37 (15)C2—C3—C4—C50.5 (3)
O2—S1—C11—C16139.67 (13)C3—C4—C5—C60.6 (3)
N1—S1—C11—C1272.33 (14)C4—C5—C6—C10.1 (3)
N1—S1—C11—C16107.63 (13)S1—C11—C12—C13178.56 (13)
O3—S2—N2—C2179.96 (12)C12—C11—C16—C152.0 (2)
O4—S2—N2—C251.87 (15)C16—C11—C12—C131.5 (2)
C21—S2—N2—C265.23 (15)S1—C11—C16—C15178.01 (12)
O3—S2—C21—C2250.77 (16)C11—C12—C13—C140.6 (3)
O3—S2—C21—C26127.61 (14)C12—C13—C14—C152.0 (3)
O4—S2—C21—C22178.68 (14)C13—C14—C15—C161.4 (3)
O4—S2—C21—C262.94 (16)C14—C15—C16—C110.6 (2)
N2—S2—C21—C2260.78 (15)C22—C21—C26—C251.4 (3)
N2—S2—C21—C26120.84 (14)S2—C21—C26—C25176.91 (14)
S1—N1—C1—C291.94 (16)S2—C21—C22—C23177.70 (14)
S1—N1—C1—C691.75 (17)C26—C21—C22—C230.7 (3)
S2—N2—C2—C1151.82 (12)C21—C22—C23—C240.6 (3)
S2—N2—C2—C330.6 (2)C22—C23—C24—C251.0 (3)
N1—C1—C2—C3175.20 (14)C23—C24—C25—C260.3 (3)
C6—C1—C2—N2176.53 (14)C24—C25—C26—C211.0 (3)
N1—C1—C2—N27.2 (2)
Symmetry codes: (i) x+2, y+1, z; (ii) x, y+3/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x+1, y+1, z; (v) x+1, y, z; (vi) x, y+3/2, z1/2; (vii) x1, y, z; (viii) x+1, y+1/2, z+1/2; (ix) x1, y+3/2, z+1/2; (x) x+1, y+3/2, z1/2; (xi) x+1, y+2, z; (xii) x+2, y1/2, z1/2; (xiii) x+2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2iv0.79 (2)2.15 (2)2.9310 (19)169 (2)
N2—H2···O10.814 (19)2.54 (2)3.0288 (18)119.6 (16)
N2—H2···N10.814 (19)2.40 (2)2.780 (2)109.7 (16)
N2—H2···O3i0.814 (19)2.275 (19)3.0318 (18)154.8 (19)
C3—H3···O40.952.353.026 (2)128
C12—H12···O3vii0.952.533.291 (2)137
C16—H16···O10.952.532.904 (2)104
C22—H22···O3i0.952.553.441 (2)157
C26—H26···O40.952.512.893 (2)104
C16—H16···Cg3ii0.952.733.573 (2)148
Symmetry codes: (i) x+2, y+1, z; (ii) x, y+3/2, z+1/2; (iv) x+1, y+1, z; (vii) x1, y, z.
 

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