PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2277.
Published online 2008 November 8. doi:  10.1107/S1600536808035526
PMCID: PMC2959804

2-Nitro-N-(4-pyridinio)benzene­sulfonamidate monohydrate

Abstract

The title compound, C11H9N3O4S·H2O, contains both an acid and a base centre and displays a zwitterionic structure. There are two independent mol­ecules and two water mol­ecules in the asymmetric unit. The dihedral angles between the benzene ring and the pyridinium ring are 109.7 (1) and 110.7 (1)°. The dihedral angles between the nitro group and the benzene ring are 116.1 (2) and 116.7 (1)°. The crystal structure is stabilized by N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds.

Related literature

For the uses of organic pyridinium salts, see: Damiano et al. (2007 [triangle]). For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007 [triangle]); Yu & Li (2007 [triangle]). For reference geometric data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2277-scheme1.jpg

Experimental

Crystal data

  • C11H9N3O4S·H2O
  • M r = 297.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2277-efi1.jpg
  • a = 8.7206 (17) Å
  • b = 11.972 (2) Å
  • c = 12.743 (3) Å
  • β = 107.65 (3)°
  • V = 1267.8 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 113 (2) K
  • 0.14 × 0.10 × 0.04 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.962, T max = 0.989
  • 10348 measured reflections
  • 4633 independent reflections
  • 3587 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.090
  • S = 1.03
  • 4633 reflections
  • 385 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.40 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1560 Friedel pairs
  • Flack parameter: 0.52 (6)

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035526/hg2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035526/hg2431Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Organic pyridinium salts have been widely used in the construction of supramolecular architectures (Damiano et al., 2007). As part of our ongoing studies of supramolecular chemistry involving the pyridinium rings (Li et al., 2007), the structure of the title compound was determined by X-ray diffraction. There are two independent molecules and two independent water molecules in the unit cell. In the cations of the title compound the short C—N distance [N2—C1 = 1.367 (3) Å and N5—C12 = 1.365 (3) Å] indicate the slight conjugation of the sulfonamide N with the pyridinium ring (Allen et al., 1987).

The dihedral angles between the benzene ring and the pyridinium ring are 109.7 (1)° and 110.7 (1)° respectively. And the dihedral angles between the nitro group and the benzene ring are 116.1 (2)° and 116.7 (1)° respectively. The crystal structure is stabilized by N—H···O hydrogen bonds.

Experimental

A solution of 2-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in CH2Cl2 (10 ml) was added dropwise to a suspension of 4-aminopyridine (0.9 g, 10 mmol) in CH2Cl2 (10 ml) at room temperature with stirring. The reaction mixture was stirred overnight. The yellow solid obtained was washed with warm water to obtain the title compound in a yield of 55.7%. A colorless single crystal suitable for X-ray analysis was obtained by slow evaporation of an NaOH (10%) solution at room temperature over a period of a week.

Refinement

The N-bound H atoms were located in a difference map and their coordinates were refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The Flack test results are ambiguous because of the presence of merohedral twin. The water O-bound H atoms were refined freely, but the O—H distances were restrained to 0.85 (1) Å, and the water HA···HB distance to 1.45 (1) Å.

Figures

Fig. 1.
View of the molecule of title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level (arbitrary spheres for the H atoms).

Crystal data

C11H9N3O4S·H2OF000 = 616
Mr = 297.29Dx = 1.557 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4439 reflections
a = 8.7206 (17) Åθ = 2.4–27.5º
b = 11.972 (2) ŵ = 0.28 mm1
c = 12.743 (3) ÅT = 113 (2) K
β = 107.65 (3)ºBlock, colourless
V = 1267.8 (4) Å30.14 × 0.10 × 0.04 mm
Z = 4

Data collection

Rigaku Saturn diffractometer4633 independent reflections
Radiation source: rotating anode3587 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.033
T = 113(2) Kθmax = 27.5º
ω scansθmin = 1.7º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)h = −11→11
Tmin = 0.962, Tmax = 0.989k = −12→15
10348 measured reflectionsl = −16→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032  w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090(Δ/σ)max = 0.002
S = 1.03Δρmax = 0.22 e Å3
4633 reflectionsΔρmin = −0.40 e Å3
385 parametersExtinction correction: none
9 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.52 (6)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
S10.54299 (7)0.49945 (5)0.75574 (5)0.01423 (14)
S21.01577 (7)0.25356 (5)0.35546 (5)0.01307 (14)
O10.36887 (19)0.49815 (17)0.72910 (14)0.0177 (4)
O20.6116 (2)0.59540 (15)0.71745 (16)0.0187 (4)
O30.4219 (3)0.29003 (18)0.87441 (18)0.0318 (5)
O40.2777 (2)0.4008 (2)0.94108 (18)0.0326 (5)
O50.9524 (2)0.15286 (15)0.38857 (15)0.0165 (4)
O61.1904 (2)0.26159 (18)0.38501 (16)0.0182 (4)
O71.1373 (3)0.46983 (18)0.24125 (19)0.0334 (5)
O81.2807 (2)0.3638 (2)0.16880 (18)0.0371 (6)
N11.0324 (3)0.2999 (2)0.67719 (19)0.0185 (5)
N20.5920 (2)0.38299 (18)0.71702 (19)0.0146 (5)
N30.4050 (3)0.3727 (2)0.9245 (2)0.0217 (5)
N40.5077 (3)0.4240 (2)0.43389 (18)0.0179 (5)
N50.9564 (2)0.36491 (18)0.39696 (18)0.0141 (5)
N61.1564 (3)0.3888 (2)0.18846 (19)0.0230 (6)
C10.7414 (3)0.3615 (2)0.7078 (2)0.0132 (5)
C20.7644 (3)0.2549 (2)0.6690 (2)0.0167 (5)
H20.68130.20290.65370.020*
C30.9100 (3)0.2265 (2)0.6532 (2)0.0188 (6)
H30.92310.15630.62590.023*
C41.0168 (3)0.4019 (2)0.7153 (2)0.0179 (6)
H41.10300.45130.73040.021*
C50.8752 (3)0.4350 (2)0.7325 (2)0.0169 (6)
H50.86720.50580.76040.020*
C60.6158 (3)0.5053 (3)0.9027 (2)0.0148 (5)
C70.7441 (3)0.5753 (2)0.9531 (2)0.0189 (6)
H70.79360.61560.91000.023*
C80.7996 (3)0.5858 (2)1.0674 (2)0.0240 (6)
H80.88570.63291.09990.029*
C90.7271 (3)0.5264 (3)1.1326 (2)0.0245 (7)
H90.76560.53251.20890.029*
C100.5978 (3)0.4582 (2)1.0843 (2)0.0208 (6)
H100.54690.41971.12770.025*
C110.5441 (3)0.4472 (2)0.9712 (2)0.0162 (6)
C120.8049 (3)0.3782 (2)0.4049 (2)0.0120 (5)
C130.7734 (3)0.4806 (2)0.4510 (2)0.0163 (6)
H130.85340.53470.47220.020*
C140.6264 (3)0.4998 (2)0.4642 (2)0.0181 (5)
H140.60780.56690.49490.022*
C150.5302 (3)0.3265 (2)0.3884 (2)0.0165 (5)
H150.44640.27520.36720.020*
C160.6767 (3)0.3014 (2)0.3725 (2)0.0136 (5)
H160.69050.23390.34050.016*
C170.9459 (3)0.2526 (2)0.2084 (2)0.0145 (5)
C180.8167 (3)0.1850 (2)0.1552 (2)0.0179 (6)
H180.76720.14230.19670.021*
C190.7603 (3)0.1799 (2)0.0417 (2)0.0229 (6)
H190.67230.13490.00800.027*
C200.8324 (3)0.2406 (3)−0.0223 (2)0.0245 (7)
H200.79330.2365−0.09870.029*
C210.9631 (3)0.3074 (2)0.0276 (2)0.0195 (6)
H211.01410.3476−0.01460.023*
C221.0173 (3)0.3137 (2)0.1415 (2)0.0157 (6)
O90.2408 (2)0.50194 (18)0.48520 (16)0.0183 (4)
O100.6923 (2)0.74683 (18)0.37557 (18)0.0203 (4)
H1A1.127 (3)0.280 (3)0.665 (3)0.054 (11)*
H4A0.411 (2)0.441 (2)0.444 (2)0.021 (8)*
H9A0.260 (3)0.500 (3)0.5558 (8)0.047 (11)*
H9B0.160 (2)0.460 (2)0.4517 (18)0.024 (9)*
H10A0.719 (4)0.751 (4)0.4468 (8)0.11 (2)*
H10B0.601 (2)0.780 (3)0.346 (2)0.034 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0127 (3)0.0152 (3)0.0156 (3)0.0016 (3)0.0055 (2)0.0026 (3)
S20.0098 (3)0.0162 (3)0.0138 (3)0.0013 (3)0.0044 (2)0.0012 (3)
O10.0119 (8)0.0220 (10)0.0201 (10)0.0049 (9)0.0064 (7)0.0009 (9)
O20.0242 (10)0.0133 (9)0.0209 (11)0.0000 (8)0.0102 (9)0.0042 (8)
O30.0376 (12)0.0285 (12)0.0288 (13)−0.0115 (10)0.0095 (10)−0.0019 (10)
O40.0157 (9)0.0515 (15)0.0329 (13)−0.0051 (10)0.0109 (9)0.0064 (12)
O50.0194 (10)0.0153 (9)0.0158 (10)0.0043 (8)0.0067 (8)0.0053 (8)
O60.0099 (8)0.0269 (11)0.0190 (10)0.0008 (9)0.0061 (7)0.0016 (9)
O70.0378 (13)0.0292 (13)0.0329 (13)−0.0111 (10)0.0101 (11)−0.0060 (10)
O80.0180 (10)0.0689 (18)0.0274 (13)−0.0077 (11)0.0114 (10)0.0055 (12)
N10.0135 (11)0.0249 (12)0.0184 (12)0.0064 (10)0.0067 (9)0.0022 (10)
N20.0116 (10)0.0147 (11)0.0196 (12)0.0000 (9)0.0078 (9)−0.0001 (9)
N30.0209 (12)0.0263 (14)0.0176 (13)−0.0040 (11)0.0057 (10)0.0071 (10)
N40.0148 (11)0.0224 (13)0.0179 (12)0.0020 (10)0.0072 (9)0.0009 (10)
N50.0108 (10)0.0177 (11)0.0144 (11)−0.0028 (9)0.0046 (9)−0.0035 (9)
N60.0193 (12)0.0354 (15)0.0146 (12)−0.0067 (11)0.0054 (10)0.0064 (11)
C10.0123 (11)0.0178 (13)0.0100 (13)0.0024 (10)0.0042 (10)0.0041 (10)
C20.0166 (11)0.0179 (12)0.0164 (13)−0.0044 (12)0.0062 (10)0.0015 (12)
C30.0177 (13)0.0173 (14)0.0217 (15)0.0033 (11)0.0062 (11)−0.0025 (11)
C40.0133 (12)0.0214 (14)0.0181 (14)−0.0009 (11)0.0035 (10)0.0014 (12)
C50.0145 (12)0.0147 (13)0.0211 (15)0.0009 (11)0.0048 (11)−0.0006 (11)
C60.0151 (12)0.0134 (13)0.0166 (13)0.0032 (12)0.0059 (10)0.0000 (12)
C70.0206 (13)0.0143 (13)0.0224 (15)−0.0036 (11)0.0075 (12)0.0006 (11)
C80.0252 (15)0.0225 (15)0.0224 (16)−0.0067 (13)0.0040 (13)−0.0035 (12)
C90.0255 (14)0.0278 (16)0.0184 (15)0.0041 (13)0.0038 (12)−0.0030 (12)
C100.0236 (14)0.0239 (15)0.0178 (15)0.0041 (12)0.0106 (12)0.0047 (12)
C110.0103 (11)0.0175 (13)0.0217 (15)0.0013 (10)0.0062 (11)0.0027 (11)
C120.0152 (12)0.0125 (12)0.0083 (12)0.0024 (10)0.0038 (10)0.0017 (10)
C130.0168 (12)0.0141 (13)0.0183 (14)−0.0048 (11)0.0060 (11)−0.0026 (11)
C140.0225 (13)0.0147 (12)0.0186 (13)−0.0018 (12)0.0087 (11)−0.0020 (12)
C150.0136 (12)0.0198 (13)0.0173 (14)0.0002 (11)0.0066 (11)−0.0031 (11)
C160.0093 (11)0.0150 (12)0.0173 (14)−0.0026 (10)0.0051 (10)−0.0032 (11)
C170.0160 (12)0.0150 (12)0.0119 (13)0.0007 (12)0.0033 (10)−0.0004 (11)
C180.0193 (13)0.0163 (14)0.0198 (15)−0.0015 (12)0.0084 (12)0.0037 (12)
C190.0262 (15)0.0190 (15)0.0202 (15)−0.0061 (13)0.0022 (12)0.0005 (12)
C200.0322 (15)0.0275 (16)0.0115 (14)0.0032 (14)0.0033 (12)−0.0006 (13)
C210.0193 (13)0.0221 (15)0.0205 (15)0.0031 (12)0.0110 (12)0.0049 (12)
C220.0118 (11)0.0181 (14)0.0172 (14)0.0001 (11)0.0045 (11)0.0019 (11)
O90.0157 (9)0.0210 (10)0.0194 (11)0.0003 (9)0.0072 (8)−0.0056 (10)
O100.0170 (9)0.0221 (10)0.0215 (11)0.0022 (9)0.0057 (8)0.0043 (10)

Geometric parameters (Å, °)

S1—O21.4464 (19)C6—C111.403 (3)
S1—O11.4521 (17)C7—C81.394 (4)
S1—N21.581 (2)C7—H70.9300
S1—C61.787 (3)C8—C91.383 (4)
S2—O51.4416 (19)C8—H80.9300
S2—O61.4568 (17)C9—C101.377 (4)
S2—N51.578 (2)C9—H90.9300
S2—C171.787 (3)C10—C111.380 (4)
O3—N31.211 (3)C10—H100.9300
O4—N31.237 (3)C12—C161.409 (3)
O7—N61.221 (3)C12—C131.421 (3)
O8—N61.221 (3)C13—C141.362 (3)
N1—C41.336 (4)C13—H130.9300
N1—C31.345 (3)C14—H140.9300
N1—H1A0.918 (10)C15—C161.385 (3)
N2—C11.367 (3)C15—H150.9300
N3—C111.478 (3)C16—H160.9300
N4—C141.342 (3)C17—C181.386 (4)
N4—C151.344 (3)C17—C221.404 (3)
N4—H4A0.913 (10)C18—C191.380 (4)
N5—C121.365 (3)C18—H180.9300
N6—C221.482 (3)C19—C201.379 (4)
C1—C21.405 (4)C19—H190.9300
C1—C51.419 (4)C20—C211.380 (4)
C2—C31.387 (3)C20—H200.9300
C2—H20.9300C21—C221.385 (4)
C3—H30.9300C21—H210.9300
C4—C51.376 (3)O9—H9A0.864 (10)
C4—H40.9300O9—H9B0.867 (10)
C5—H50.9300O10—H10A0.867 (10)
C6—C71.389 (4)O10—H10B0.870 (10)
O2—S1—O1116.08 (11)C9—C8—C7120.3 (3)
O2—S1—N2114.62 (10)C9—C8—H8119.9
O1—S1—N2106.27 (11)C7—C8—H8119.9
O2—S1—C6105.68 (13)C10—C9—C8119.8 (3)
O1—S1—C6105.03 (11)C10—C9—H9120.1
N2—S1—C6108.55 (13)C8—C9—H9120.1
O5—S2—O6116.29 (11)C9—C10—C11119.8 (3)
O5—S2—N5114.48 (10)C9—C10—H10120.1
O6—S2—N5106.33 (12)C11—C10—H10120.1
O5—S2—C17105.23 (12)C10—C11—C6121.9 (3)
O6—S2—C17105.61 (11)C10—C11—N3117.1 (2)
N5—S2—C17108.33 (12)C6—C11—N3121.0 (2)
C4—N1—C3121.3 (2)N5—C12—C16127.0 (2)
C4—N1—H1A120 (2)N5—C12—C13116.4 (2)
C3—N1—H1A119 (2)C16—C12—C13116.6 (2)
C1—N2—S1123.21 (19)C14—C13—C12120.2 (2)
O3—N3—O4124.9 (3)C14—C13—H13119.9
O3—N3—C11119.3 (2)C12—C13—H13119.9
O4—N3—C11115.9 (2)N4—C14—C13121.6 (3)
C14—N4—C15120.7 (2)N4—C14—H14119.2
C14—N4—H4A118.3 (19)C13—C14—H14119.2
C15—N4—H4A121.0 (19)N4—C15—C16120.9 (2)
C12—N5—S2123.16 (18)N4—C15—H15119.6
O7—N6—O8125.8 (3)C16—C15—H15119.6
O7—N6—C22118.2 (2)C15—C16—C12120.0 (2)
O8—N6—C22115.9 (2)C15—C16—H16120.0
N2—C1—C2116.3 (2)C12—C16—H16120.0
N2—C1—C5127.2 (2)C18—C17—C22116.9 (2)
C2—C1—C5116.5 (2)C18—C17—S2119.0 (2)
C3—C2—C1120.6 (2)C22—C17—S2124.1 (2)
C3—C2—H2119.7C19—C18—C17121.1 (2)
C1—C2—H2119.7C19—C18—H18119.4
N1—C3—C2120.3 (2)C17—C18—H18119.4
N1—C3—H3119.8C20—C19—C18121.0 (3)
C2—C3—H3119.8C20—C19—H19119.5
N1—C4—C5121.1 (3)C18—C19—H19119.5
N1—C4—H4119.5C19—C20—C21119.6 (3)
C5—C4—H4119.5C19—C20—H20120.2
C4—C5—C1120.2 (2)C21—C20—H20120.2
C4—C5—H5119.9C20—C21—C22119.1 (3)
C1—C5—H5119.9C20—C21—H21120.4
C7—C6—C11117.3 (2)C22—C21—H21120.4
C7—C6—S1119.3 (2)C21—C22—C17122.3 (2)
C11—C6—S1123.3 (2)C21—C22—N6115.7 (2)
C6—C7—C8120.9 (3)C17—C22—N6122.0 (2)
C6—C7—H7119.6H9A—O9—H9B111.6 (16)
C8—C7—H7119.6H10A—O10—H10B110.7 (16)
O2—S1—N2—C136.7 (2)O4—N3—C11—C1062.9 (3)
O1—S1—N2—C1166.3 (2)O3—N3—C11—C664.4 (4)
C6—S1—N2—C1−81.2 (2)O4—N3—C11—C6−116.0 (3)
O5—S2—N5—C12−36.0 (2)S2—N5—C12—C16−4.2 (4)
O6—S2—N5—C12−165.8 (2)S2—N5—C12—C13175.7 (2)
C17—S2—N5—C1281.0 (2)N5—C12—C13—C14−178.5 (2)
S1—N2—C1—C2−178.07 (19)C16—C12—C13—C141.4 (4)
S1—N2—C1—C51.5 (4)C15—N4—C14—C13−0.6 (4)
N2—C1—C2—C3177.8 (2)C12—C13—C14—N4−0.4 (4)
C5—C1—C2—C3−1.9 (4)C14—N4—C15—C160.6 (4)
C4—N1—C3—C2−0.8 (4)N4—C15—C16—C120.4 (4)
C1—C2—C3—N11.4 (4)N5—C12—C16—C15178.5 (2)
C3—N1—C4—C50.7 (4)C13—C12—C16—C15−1.3 (4)
N1—C4—C5—C1−1.2 (4)O5—S2—C17—C1818.6 (2)
N2—C1—C5—C4−177.8 (3)O6—S2—C17—C18142.2 (2)
C2—C1—C5—C41.8 (4)N5—S2—C17—C18−104.2 (2)
O2—S1—C6—C7−14.8 (2)O5—S2—C17—C22−159.0 (2)
O1—S1—C6—C7−138.0 (2)O6—S2—C17—C22−35.5 (3)
N2—S1—C6—C7108.6 (2)N5—S2—C17—C2278.1 (2)
O2—S1—C6—C11161.6 (2)C22—C17—C18—C19−1.0 (4)
O1—S1—C6—C1138.3 (3)S2—C17—C18—C19−178.8 (2)
N2—S1—C6—C11−75.0 (2)C17—C18—C19—C201.1 (4)
C11—C6—C7—C80.6 (4)C18—C19—C20—C210.1 (4)
S1—C6—C7—C8177.2 (2)C19—C20—C21—C22−1.2 (4)
C6—C7—C8—C9−0.1 (4)C20—C21—C22—C171.3 (4)
C7—C8—C9—C10−1.1 (4)C20—C21—C22—N6−179.0 (2)
C8—C9—C10—C111.7 (4)C18—C17—C22—C21−0.2 (4)
C9—C10—C11—C6−1.2 (4)S2—C17—C22—C21177.5 (2)
C9—C10—C11—N3180.0 (2)C18—C17—C22—N6−179.9 (2)
C7—C6—C11—C100.0 (4)S2—C17—C22—N6−2.2 (4)
S1—C6—C11—C10−176.4 (2)O7—N6—C22—C21116.6 (3)
C7—C6—C11—N3178.8 (2)O8—N6—C22—C21−62.4 (3)
S1—C6—C11—N32.4 (4)O7—N6—C22—C17−63.7 (4)
O3—N3—C11—C10−116.7 (3)O8—N6—C22—C17117.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O90.913 (10)1.868 (12)2.764 (3)167 (3)
O9—H9A···O10.864 (10)2.122 (11)2.967 (3)166 (3)
N1—H1A···O10i0.918 (10)1.843 (11)2.757 (3)174 (4)
O9—H9B···N5ii0.867 (10)2.043 (11)2.901 (3)170 (2)
O9—H9B···O6ii0.867 (10)2.56 (2)3.125 (3)123 (2)
O10—H10A···O6iii0.867 (10)2.051 (11)2.914 (3)174 (4)
O10—H10B···N2iv0.870 (10)2.042 (12)2.902 (3)170 (3)

Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2431).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem.5, 2735—2752. [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Li, J.-S., Chen, L.-G., Zhang, Y.-Y., Xu, Y.-J., Deng, Y., Zeng, T. & Huang, P.-M. (2007). J. Chem. Res. pp. 350–352.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography