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The structure of title compound, C6H16N+·C14H8N3O7S, comprises discrete ions which are inter­connected by N—H...O and N—H+...O hydrogen bonds, leading to a neutral one-dimensional network along [100]. These hydrogen bonds appear to complement the Coulombic inter­action and help to stabilize the structure further.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106050840/ln3028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106050840/ln3028Isup2.hkl
Contains datablock I

CCDC reference: 634903

Comment top

Sulfenamides are important compounds with versatile industrial applications (Kuhle, 1973). 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-dinitrophenylsulfenyl chloride and 2-carbamoyl benzoic acid. As part of our work involving the study of the synthesis and structural characterization of divalent-sulfur compounds (Brito et al., 2004, 2005; Brito, López-Rodríguez, Cárdenas & Vargas, 2006; Brito, López-Rodríguez, Vargas & León, 2006), we report here the molecular and supramolecular structure of (I). To our knowledge (Cambridge Structural Database, version 5.27; Allen, 2002), this is the first reported structure of an ionic sulfenamide.

The structure of compound (I) comprises discrete ions (Fig. 1 and Table 1). The cation in (I) has an approximate C2 symmetry and the molecular dimensions are within normal ranges (Allen et al., 1987), with mean Csp3—Csp3 = 1.508 (4) Å and mean Csp3—N = 1.504 (3) Å.

The benzene rings are slightly distorted and the nitro groups are slightly twisted with respect to the ring to which they are bonded (Table 1). The C—S and N—S bond distances [1.760 (2) and 1.6885 (18) Å, respectively] are normal for this type of compound [literature values are in the ranges C—S = 1.763–1.791 Å and S—N = 1.679–1.695 Å (Mahmoudkhani & Vargas-Baca, 2003; Glidewell et al., 2003; Lee et al., 1995; Zhang et al., 2005; Bao et al., 2003)]. The S—N distance is shorter than the normal S—N single-bond length (1.74 Å; Pauling, 1960), but is normal for this type of structure as a result of the π character of the S—N bond.

The C—O bond distances in the carboxylate group are nearly equal and lie midway between the usual single and double C—O bond lengths found in a carboxylate fragment, as a consequence of the virtually complete electron delocalization. These lengths also compare favourably with those reported [1.2593 (16)–1.259 (2) Å] by Parvez et al. (2004), as a representative example. In the anion, the C6/S1/N3 plane makes a dihedral angle of 88.4 (8)° with the H3/N3/C7 plane, in good agreement with the value of 90.0° for the torsional ground state of this type of species. The conformation of the anion is stabilized by two intramolecular hydrogen bonds involving atom C5 as a donor, C5—H5···N3 and C5—H5···O7 (Fig. 1). The crystal packing also shows a weak intramolecular C—H···π interaction between pairs of cations and anions (Fig. 1, Table 2).

Two cations in (I) bridge two anions through N+—H···O hydrogen bonds (Table 2). The ammonium atom N4 forms hydrogen bonds to a different carboxylate O atom in each of two adjacent anions, to form a centrosymmetric macroring at (0, 0, 1/2) characterized by the R44(12) motif (labelled A in Fig. 2) (Bernstein et al., 1995). Pairs of anions are then connected via hydrogen bonds involving atom N3 as the donor in one anion and atom O6 of the carboxylate group of the other anion as the acceptor, thereby generating an R22(14) centrosymmetric ring (labelled B in Fig. 2) at (1/2, 0, 1/2). These two types of rings combine alternately in an ···ABAB··· fashion to form a one-dimensional supramolecular aggregate (Fig. 2).

Experimental top

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, 2-carbamoylbenzoic acid, C8H7NO3, was prepared in situ by a hydrolysis reaction at room temperature of the phthalimide compound (see scheme). The title compound, (I), was prepared according to the method of Wunderly (1972). A methanol solution of 2,4-dinitrophenyl chloride (2.487 g, 0.010 mol) was added dropwise to a stirred solution of phthalimide (1.176 g, 0.008 mol) and diisopropylamine (1.13 ml, 0.008 mol) in dimethylformamide–H2O (5:1 v/v, Volume?) under a nitrogen atmosphere. Stirring was continued for 30 min at 298 K. The colourless crystals which formed were filtered off, washed with pentane and dried at room temperature. Colourless crystals suitable for single-crystal X-ray diffraction studies were obtained by slow evaporation of a solution of (I) in methanol [m.p. 423 K (decomposition)]. FT–IR (KBr pellet, cm−1): ν(w, C—S) 735; ν(s, CO) 1568; ν(s, N—H) 3106; ν(s, NO2) 1521; ν(s, C—O) 1307; ν(m, S—N) 967; ν(s, C—H disubstitution, Ar) 830; ν(m, N—H amine) 2942.

Refinement top

H atoms bonded to atoms N3 and N4 were located in difference density maps and refined with an isotropic model, giving N—H distances in the range 0.82 (3)–0.93 (3) Å. H atoms bonded to C were positioned geometrically and then allowed to ride on their parent atoms, with C—H distances of 0.94 Å for aromatic H atoms, 0.96 Å for methyl H atoms and 0.98 Å for methylene H atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl groups. 55 unique reflections with sinθ/λ < 0.6 were not included in the data set as they were either partially obscured by the beam stop or were eliminated during data reduction.

Computing details top

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), Mercury (Macrae et al., 2006) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme and with 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. The dashed lines denote the hydrogen-bonding interactions and the C—H···π interaction (centroid C9—C14 ring) within the asymmetric unit.
[Figure 2] Fig. 2. A view of the one-dimensional supramolecular aggregate, showing the formation of R44(12) and R22(14) rings (labelled A and B, respectively). H atoms not involved in the N—H···O interactions have been omitted. [Symmetry codes: (i) −x, −y, 1 − z; (ii) 1 − x, −y, 1 − z.]
Diisopropylammonium 2-[(2,4-dinitrophenyl)sulfanylaminocarbonyl]benzoate top
Crystal data top
C6H16N+·C14H8N3O7SF(000) = 976
Mr = 464.49Dx = 1.36 Mg m3
Monoclinic, P21/nMelting point: 422.8 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.435 (1) ÅCell parameters from 6570 reflections
b = 18.098 (8) Åθ = 2.0–26.5°
c = 13.612 (2) ŵ = 0.19 mm1
β = 102.485 (9)°T = 298 K
V = 2269.3 (11) Å3Prism, colourless
Z = 40.35 × 0.23 × 0.19 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4866 independent reflections
Radiation source: fine-focus sealed tube4116 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ scans, and ω scans with κ offsetsθmax = 27°, θmin = 1.9°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1012
Tmin = 0.951, Tmax = 0.963k = 2320
12285 measured reflectionsl = 1710
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.0801P)2 + 0.6445P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166(Δ/σ)max = 0.006
S = 1.17Δρmax = 0.41 e Å3
4866 reflectionsΔρmin = 0.36 e Å3
307 parameters
Crystal data top
C6H16N+·C14H8N3O7SV = 2269.3 (11) Å3
Mr = 464.49Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.435 (1) ŵ = 0.19 mm1
b = 18.098 (8) ÅT = 298 K
c = 13.612 (2) Å0.35 × 0.23 × 0.19 mm
β = 102.485 (9)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4866 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
4116 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.963Rint = 0.037
12285 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.41 e Å3
4866 reflectionsΔρmin = 0.36 e Å3
307 parameters
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
S10.44359 (6)0.11628 (3)0.21640 (4)0.04332 (19)
O10.0037 (3)0.13080 (11)0.05426 (14)0.0715 (6)
O20.0615 (2)0.14362 (12)0.08809 (16)0.0764 (6)
O30.3719 (3)0.03832 (13)0.08998 (14)0.0764 (6)
O40.4464 (3)0.11826 (12)0.02576 (15)0.0773 (7)
O50.2862 (2)0.19101 (11)0.35562 (13)0.0628 (5)
O60.29183 (16)0.03871 (8)0.55993 (12)0.0457 (4)
O70.18012 (16)0.04121 (9)0.44480 (11)0.0449 (4)
N10.0121 (2)0.11651 (11)0.03470 (16)0.0524 (5)
N20.3767 (2)0.06355 (12)0.00645 (15)0.0517 (5)
N30.4509 (2)0.10309 (10)0.34020 (13)0.0373 (4)
N40.0550 (2)0.13591 (10)0.44750 (13)0.0368 (4)
C10.2976 (2)0.02649 (12)0.06055 (15)0.0383 (5)
C20.2025 (2)0.02849 (12)0.01862 (16)0.0411 (5)
H20.19410.0430.04790.056 (2)*
C30.1205 (2)0.06105 (12)0.07883 (16)0.0410 (5)
C40.1334 (3)0.04063 (13)0.17770 (16)0.0435 (5)
H40.07550.06290.21640.056 (2)*
C50.2315 (2)0.01249 (12)0.21916 (15)0.0402 (5)
H50.24130.0250.28660.056 (2)*
C60.3175 (2)0.04828 (11)0.16185 (15)0.0355 (4)
C70.3781 (2)0.14691 (11)0.39419 (16)0.0379 (5)
C80.2780 (2)0.02379 (11)0.51882 (15)0.0347 (4)
C90.4302 (2)0.13935 (11)0.50707 (15)0.0354 (4)
C100.3862 (2)0.08276 (11)0.56444 (15)0.0359 (4)
C110.4381 (3)0.08354 (13)0.66844 (16)0.0458 (5)
H110.41050.04620.70740.056 (2)*
C120.5298 (3)0.13888 (15)0.71471 (19)0.0578 (7)
H120.56070.13940.78440.056 (2)*
C130.5754 (3)0.19301 (14)0.6581 (2)0.0577 (7)
H130.63870.22970.68890.056 (2)*
C140.5262 (3)0.19261 (13)0.55454 (19)0.0491 (6)
H140.55840.22890.51610.056 (2)*
C150.1145 (3)0.11360 (19)0.2671 (2)0.0703 (8)
H15A0.03640.07850.27840.096 (3)*
H15B0.12360.13550.20180.096 (3)*
H15C0.20340.0890.27060.096 (3)*
C160.0833 (2)0.17312 (14)0.34648 (15)0.0443 (5)
H160.00470.19960.33970.056 (2)*
C170.2064 (3)0.22806 (16)0.3359 (2)0.0628 (7)
H17A0.29020.20410.35050.096 (3)*
H17B0.22930.24680.26830.096 (3)*
H17C0.17770.26820.38210.096 (3)*
C180.0283 (3)0.18572 (13)0.53829 (16)0.0452 (5)
H180.1120.21870.53320.056 (2)*
C190.1054 (3)0.23224 (14)0.54382 (19)0.0531 (6)
H19A0.18930.20080.55330.096 (3)*
H19B0.11530.2660.59930.096 (3)*
H19C0.09690.25950.48240.096 (3)*
C200.0176 (5)0.1380 (2)0.6301 (2)0.0895 (12)
H20A0.06590.10650.63750.096 (3)*
H20B0.10350.10820.62290.096 (3)*
H20C0.00860.16880.68860.096 (3)*
H4A0.021 (3)0.1094 (13)0.4526 (17)0.039 (6)*
H4B0.132 (3)0.1046 (14)0.4519 (19)0.049 (7)*
H30.521 (3)0.0801 (15)0.372 (2)0.051 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0447 (3)0.0502 (3)0.0336 (3)0.0110 (2)0.0053 (2)0.0020 (2)
O10.1023 (16)0.0657 (12)0.0452 (11)0.0299 (11)0.0132 (10)0.0135 (9)
O20.0890 (15)0.0809 (14)0.0649 (13)0.0454 (12)0.0290 (11)0.0103 (11)
O30.1006 (16)0.0985 (15)0.0398 (10)0.0286 (13)0.0367 (10)0.0082 (10)
O40.0996 (16)0.0828 (14)0.0534 (12)0.0474 (13)0.0254 (11)0.0010 (10)
O50.0665 (11)0.0694 (12)0.0503 (10)0.0330 (10)0.0077 (9)0.0136 (9)
O60.0413 (8)0.0415 (8)0.0501 (10)0.0000 (7)0.0012 (7)0.0113 (7)
O70.0423 (8)0.0494 (9)0.0371 (8)0.0069 (7)0.0044 (6)0.0018 (7)
N10.0665 (13)0.0458 (11)0.0444 (12)0.0159 (10)0.0105 (10)0.0043 (9)
N20.0590 (12)0.0622 (12)0.0366 (11)0.0116 (10)0.0162 (9)0.0057 (9)
N30.0375 (9)0.0405 (9)0.0302 (9)0.0045 (8)0.0005 (7)0.0009 (7)
N40.0361 (9)0.0425 (10)0.0302 (9)0.0041 (9)0.0034 (7)0.0014 (7)
C10.0422 (11)0.0444 (11)0.0303 (10)0.0004 (9)0.0119 (8)0.0042 (8)
C20.0533 (13)0.0434 (11)0.0277 (10)0.0030 (10)0.0108 (9)0.0021 (8)
C30.0487 (12)0.0388 (11)0.0347 (11)0.0059 (9)0.0072 (9)0.0009 (9)
C40.0501 (12)0.0503 (12)0.0311 (11)0.0095 (10)0.0113 (9)0.0046 (9)
C50.0441 (11)0.0506 (12)0.0260 (10)0.0061 (10)0.0078 (8)0.0010 (9)
C60.0370 (10)0.0392 (10)0.0292 (10)0.0011 (8)0.0052 (8)0.0037 (8)
C70.0359 (10)0.0371 (10)0.0382 (11)0.0024 (9)0.0025 (8)0.0027 (9)
C80.0330 (10)0.0393 (10)0.0316 (10)0.0076 (8)0.0067 (8)0.0002 (8)
C90.0356 (10)0.0328 (10)0.0352 (11)0.0071 (8)0.0018 (8)0.0036 (8)
C100.0368 (10)0.0352 (10)0.0326 (10)0.0099 (8)0.0010 (8)0.0023 (8)
C110.0577 (14)0.0436 (12)0.0326 (11)0.0114 (11)0.0023 (10)0.0025 (9)
C120.0685 (16)0.0583 (15)0.0375 (13)0.0141 (13)0.0087 (11)0.0145 (11)
C130.0619 (15)0.0480 (13)0.0547 (15)0.0006 (12)0.0064 (12)0.0207 (12)
C140.0527 (13)0.0384 (11)0.0535 (14)0.0006 (10)0.0055 (11)0.0061 (10)
C150.0662 (17)0.107 (2)0.0353 (13)0.0155 (16)0.0067 (12)0.0129 (14)
C160.0389 (11)0.0651 (14)0.0282 (10)0.0009 (10)0.0053 (8)0.0080 (10)
C170.0643 (16)0.0630 (16)0.0523 (15)0.0136 (13)0.0070 (12)0.0094 (13)
C180.0519 (13)0.0530 (13)0.0306 (11)0.0043 (11)0.0086 (9)0.0032 (9)
C190.0551 (14)0.0481 (13)0.0535 (15)0.0001 (11)0.0057 (11)0.0119 (11)
C200.131 (3)0.101 (3)0.0317 (14)0.037 (2)0.0074 (16)0.0059 (15)
Geometric parameters (Å, º) top
S1—N31.6885 (18)C9—C141.384 (3)
S1—C61.760 (2)C9—C101.404 (3)
O1—N11.215 (3)C10—C111.394 (3)
O2—N11.212 (3)C11—C121.383 (4)
O3—N21.217 (3)C11—H110.93
O4—N21.217 (3)C12—C131.372 (4)
O5—C71.212 (3)C12—H120.93
O6—C81.256 (3)C13—C141.385 (3)
O7—C81.251 (2)C13—H130.93
N1—C31.466 (3)C14—H140.93
N2—C11.461 (3)C15—C161.509 (4)
N3—C71.363 (3)C15—H15A0.96
N3—H30.82 (3)C15—H15B0.96
N4—C161.502 (3)C15—H15C0.96
N4—C181.506 (3)C16—C171.511 (4)
N4—H4A0.85 (3)C16—H160.98
N4—H4B0.93 (3)C17—H17A0.96
C1—C21.378 (3)C17—H17B0.96
C1—C61.407 (3)C17—H17C0.96
C2—C31.375 (3)C18—C201.505 (4)
C2—H20.93C18—C191.505 (3)
C3—C41.375 (3)C18—H180.98
C4—C51.369 (3)C19—H19A0.96
C4—H40.93C19—H19B0.96
C5—C61.400 (3)C19—H19C0.96
C5—H50.93C20—H20A0.96
C7—C91.515 (3)C20—H20B0.96
C8—C101.514 (3)C20—H20C0.96
N3—S1—C6101.56 (9)C12—C11—H11119.4
O2—N1—O1123.2 (2)C10—C11—H11119.4
O2—N1—C3118.1 (2)C13—C12—C11120.2 (2)
O1—N1—C3118.6 (2)C13—C12—H12119.9
O4—N2—O3123.4 (2)C11—C12—H12119.9
O4—N2—C1117.26 (19)C12—C13—C14119.4 (2)
O3—N2—C1119.4 (2)C12—C13—H13120.3
C7—N3—S1122.62 (15)C14—C13—H13120.3
C7—N3—H3117.2 (19)C9—C14—C13121.4 (2)
S1—N3—H3116.7 (19)C9—C14—H14119.3
C16—N4—C18116.60 (18)C13—C14—H14119.3
C16—N4—H4A107.9 (16)C16—C15—H15A109.5
C18—N4—H4A106.4 (16)C16—C15—H15B109.5
C16—N4—H4B110.2 (15)H15A—C15—H15B109.5
C18—N4—H4B107.8 (16)C16—C15—H15C109.5
H4A—N4—H4B108 (2)H15A—C15—H15C109.5
C2—C1—C6123.04 (19)H15B—C15—H15C109.5
C2—C1—N2116.60 (19)N4—C16—C15107.7 (2)
C6—C1—N2120.34 (19)N4—C16—C17111.30 (19)
C3—C2—C1117.5 (2)C15—C16—C17112.0 (2)
C3—C2—H2121.2N4—C16—H16108.6
C1—C2—H2121.2C15—C16—H16108.6
C2—C3—C4121.7 (2)C17—C16—H16108.6
C2—C3—N1118.8 (2)C16—C17—H17A109.5
C4—C3—N1119.43 (19)C16—C17—H17B109.5
C5—C4—C3120.1 (2)H17A—C17—H17B109.5
C5—C4—H4120C16—C17—H17C109.5
C3—C4—H4120H17A—C17—H17C109.5
C4—C5—C6121.12 (19)H17B—C17—H17C109.5
C4—C5—H5119.4C20—C18—C19112.0 (2)
C6—C5—H5119.4C20—C18—N4107.9 (2)
C5—C6—C1116.47 (19)C19—C18—N4111.44 (19)
C5—C6—S1120.57 (16)C20—C18—H18108.5
C1—C6—S1122.96 (16)C19—C18—H18108.5
O5—C7—N3123.1 (2)N4—C18—H18108.5
O5—C7—C9122.93 (19)C18—C19—H19A109.5
N3—C7—C9113.81 (17)C18—C19—H19B109.5
O7—C8—O6125.0 (2)H19A—C19—H19B109.5
O7—C8—C10117.87 (18)C18—C19—H19C109.5
O6—C8—C10117.15 (17)H19A—C19—H19C109.5
C14—C9—C10119.40 (19)H19B—C19—H19C109.5
C14—C9—C7116.53 (19)C18—C20—H20A109.5
C10—C9—C7124.07 (18)C18—C20—H20B109.5
C11—C10—C9118.44 (19)H20A—C20—H20B109.5
C11—C10—C8118.76 (19)C18—C20—H20C109.5
C9—C10—C8122.69 (17)H20A—C20—H20C109.5
C12—C11—C10121.2 (2)H20B—C20—H20C109.5
C6—S1—N3—C7100.66 (18)S1—N3—C7—C9164.32 (14)
O4—N2—C1—C2170.7 (2)O5—C7—C9—C1477.4 (3)
O3—N2—C1—C210.3 (3)N3—C7—C9—C1498.5 (2)
O4—N2—C1—C67.9 (3)O5—C7—C9—C10102.2 (3)
O3—N2—C1—C6171.1 (2)N3—C7—C9—C1081.9 (2)
C6—C1—C2—C32.4 (3)C14—C9—C10—C111.9 (3)
N2—C1—C2—C3176.2 (2)C7—C9—C10—C11177.71 (19)
C1—C2—C3—C40.9 (3)C14—C9—C10—C8178.08 (19)
C1—C2—C3—N1176.3 (2)C7—C9—C10—C81.5 (3)
O2—N1—C3—C2178.5 (2)O7—C8—C10—C11143.9 (2)
O1—N1—C3—C21.5 (3)O6—C8—C10—C1134.5 (3)
O2—N1—C3—C41.2 (4)O7—C8—C10—C932.3 (3)
O1—N1—C3—C4175.8 (2)O6—C8—C10—C9149.25 (19)
C2—C3—C4—C51.1 (4)C9—C10—C11—C120.5 (3)
N1—C3—C4—C5178.3 (2)C8—C10—C11—C12175.9 (2)
C3—C4—C5—C61.6 (3)C10—C11—C12—C132.2 (4)
C4—C5—C6—C10.2 (3)C11—C12—C13—C141.4 (4)
C4—C5—C6—S1179.79 (17)C10—C9—C14—C132.6 (3)
C2—C1—C6—C51.9 (3)C7—C9—C14—C13176.9 (2)
N2—C1—C6—C5176.66 (19)C12—C13—C14—C91.0 (4)
C2—C1—C6—S1177.71 (17)C18—N4—C16—C15177.1 (2)
N2—C1—C6—S13.8 (3)C18—N4—C16—C1754.0 (3)
N3—S1—C6—C513.6 (2)C16—N4—C18—C20174.4 (2)
N3—S1—C6—C1165.92 (17)C16—N4—C18—C1962.3 (3)
S1—N3—C7—O511.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.82 (3)1.96 (3)2.770 (3)170 (3)
N4—H4A···O70.85 (3)1.96 (3)2.810 (3)171 (2)
N4—H4B···O6ii0.93 (3)1.90 (3)2.828 (3)172 (2)
C5—H5···O70.932.373.253 (3)160
C5—H5···N30.932.412.866 (3)110
C19—H19A···Cg10.962.923.857 (3)165
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC6H16N+·C14H8N3O7S
Mr464.49
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.435 (1), 18.098 (8), 13.612 (2)
β (°) 102.485 (9)
V3)2269.3 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.35 × 0.23 × 0.19
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.951, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
12285, 4866, 4116
Rint0.037
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.166, 1.17
No. of reflections4866
No. of parameters307
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.36

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), Mercury (Macrae et al., 2006) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
O5—C71.212 (3)O7—C81.251 (2)
O6—C81.256 (3)N3—C71.363 (3)
O3—N2—C1—C6171.1 (2)O1—N1—C3—C4175.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.82 (3)1.96 (3)2.770 (3)170 (3)
N4—H4A···O70.85 (3)1.96 (3)2.810 (3)171 (2)
N4—H4B···O6ii0.93 (3)1.90 (3)2.828 (3)172 (2)
C5—H5···O70.932.373.253 (3)160
C5—H5···N30.932.412.866 (3)110
C19—H19A···Cg10.962.923.857 (3)165
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.
 

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