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The crystal structures of three proton-transfer compounds of 5-sulfosalicylic acid (3-carboxy-4-hydroxy­benzene­sulfonic acid) with 4-X-substituted anilines (X = F, Cl and Br), namely 4-fluoro­anilinium 5-sulfosalicylate (3-carboxy-4-hydroxybenzenesulfonate) monohydrate, C6H7FN+·C7H5O6S-·H2O, (I), 4-chloro­anilinium 5-sulfosalicylate hemihydrate, C6H7ClN+·C7H5O6S-·0.5H2O, (II), and 4-bromo­anilinium 5-sulfosalicylate monohydrate, C6H7BrN+·C7H5O6S-·H2O, (III), have been determined. The asymmetric unit in (II) contains two formula units. All three compounds have three-dimensional hydrogen-bonded polymeric structures in which both the water molecule and the carboxylic acid group are involved in structure extension. With both (II) and (III), which are structurally similar, the common cyclic R_{2}^{2}(8) dimeric carboxylic acid association is present, whereas in (I), an unusual cyclic R_{3}^{3}(8) association involving all three hetero-species is found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104033451/bm1595sup1.cif
Contains datablocks global, (I), (II), (III)

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104033451/bm1595Isup2.hkl
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270104033451/bm1595IIsup3.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270104033451/bm1595IIIsup4.hkl
Contains datablock III

CCDC references: 264810; 264811; 264812

Comment top

3-Carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid, 5-SSA) has proved a particularly useful synthon for molecular assembly through hydrogen bonding, having, in addition to the primary sulfonic acid functional group, interactive carboxylic acid and phenol substituent groups. In the 5-SSA anion formed in the reaction of 5-SSA with Lewis bases, all of these substituent groups provide hydrogen-bonding donor or acceptor atoms with potential for both primary and secondary structure extension. In a previous study of the proton-transfer compounds of 5-SSA with a series of quinolines (Smith, Wermuth & White, 2004), we reviewed the structural systematics of 5-SSA compounds with Lewis bases, including those with aniline (1:1) (Bakasova et al., 1991), guanidine [both a 1:1 anhydrate (Zhang et al., 2004) and a 2:1 monohydrate (Smith, Wermuth & Healy, 2004)], theophylline (a 1:1 monohydrate) (Madarasz et al., 2002), trimethoprim (a 1:1 dihydrate) (Raj et al., 2003) and 4,4'-bipyridine (a 1:2 dihydrate) (Muthiah et al., 2003). It was observed that, with the majority of compounds, water was incorporated into the crystal structure and was involved in primary direct hydrogen-bonding interactions with the aminium groups, whereas with the anhydrous compounds, the primary interaction involved the aminium H atoms and sulfonate O-atom acceptors. In some examples, particularly those with the polycyclic heteroaromatic amines (Smith, Wermuth & White, 2004), the structures featured ππ hetero- and homomolecular interactions.

The crystal structures reported here are those of 5-SSA with the 4-halo-substituted anilines 4-fluoroaniline (FAN) [4-fluoroanilinium 5-sulfosalicylate monohydrate, C6H7FN+·C7H5O2S·H2O, (I)], 4-chloroaniline (CLAN) [4-chloroanilinium 5-sulfosalicylate hemihydrate, C6H7ClN+·C7H5O2S·0.5H2O, (II)] and 4-bromoaniline (BRAN) [4-bromoanilinium 5-sulfosalicylate monohydrate, C6H7BrN+·C7H5O2S·H2O, (III)]. Fig. 1 shows the atom-numbering scheme used for the substituted anilinium cation, the 5-sulfosalicylate anion and the water molecules of solvation in (I); the same scheme is employed for (II) and (III) and has previously been employed in 5-SSA structures reported by this group (Smith, Wermuth & Healy, 2004; Smith, Wermuth & White, 2004). Table 1 lists the selected bond distances and angles for (I)–(III). All three examples involve proton transfer from the sulfonic acid group to the amine groups of the aniline molecule, with subsequent hydrogen bonding (Tables 2a–2c) involving also the water molecule, giving in all cases three-dimensional network structures. The hydrogen bonding includes one type not encountered before in 5-SSA Lewis base compounds, namely a rare cyclic R33(8) association in (I), involving both an anilinium N+H···O(sulfonate) and an N+—H···O(water) interaction (Fig. 1). There is no occurrence of the anilinium–sulfonate R22(8) dimer interaction commonly found in the anhydrous guanidinium sulfonates (Russell et al., 1994; Zhang et al., 2004; Haynes et al., 2004) but absent in tris(guanidinium) 5-sulfosalicylate hydrate (Smith, Wermuth & Healy, 2004) and the quinolinium 5-sulfosalicylate structures (Smith, Wermuth & White, 2004). However, the common homomolecular cyclic R22(8) carboxylic acid association is found in both (II) and (III).

With the 5-SSA anion species in (I)–(III), structural and conformational features similar to those previously observed (Smith, Wermuth & White, 2004) are found. The usual intramolecular hydrogen bond is found between the phenol OH group and a carboxylate O atom (O2—H2···O72) [2.598 (3)–2.625 (2) Å], essentially giving coplanarity of the carboxylic acid group and the benzene ring [torsion angle C2—C1—C7—O71, range 176.0 (3)–178.9 (2)°]. However, in only one compound, (I), is the carboxylic acid group involved in the strong single heteromolecular OH···O(sulfonate) hydrogen-bonding interaction [2.632 (2) Å], such as is found in most 5-SSA compounds. With (II) and (III) this group participates in the equally strong but cyclic homo-intermolecular interaction, while in none of the structures is there any intermolecular phenol O-atom participation.

## AUTHOR: Please check Figure numbers in all Comment text. ## AUTHOR: Please supply symmetry codes as noted below.

Compound (I) with 4-fluoroaniline, [FAN+.5-SSA·H2O] (Fig. 1), comprises layers of cation and anion pairs which propagate along the 21 screw axis in the cell, linked by hydrogen- bonding interactions both within and between the layers (Table 2). The anilinium group is involved in three hydrogen-bonding interactions, two of which comprise direct N+H···O(sulfonate) links, [N11···O53 and N11···O51ii; symmetry code: (ii) ??????], the third being a link to the water molecule (N11···O1W). One of the water H atoms completes an unusual R33(8) cyclic association with a second sulfonate O atom (O1W···O52), while the second forms an interlayer bridge with another sulfonate O atom [O53i; symmetry code: (i) ????????]. The result is that the water molecule effectively links together the cation/anion layers that form along the a cell direction. The carboxylate group of 5-SSA also gives a link along the c cell direction [O71···O52iii; symmetry code: (iii) ??????], resulting in a three-dimensional hydrogen-bonded network structure (Fig. 2).

Although (II) is a hemihydrate, both compound (II) with 4-chloroaniline, [CLAN+.5-SSA·0.5H2O], and compound (III), with 4-bromoaniline, [BRAN+ 5-SSA·H2O], are structurally similar. This similarity may be seen in Figs. 5 and 6. In both examples, the common R22(8) hydrogen- bonded cyclic carboxylic acid dimer is found, which in the case of (III) lies across a crystallographic inversion centre [O71···O72i = 2.639 (3) Å; symmetry code: (i) ?????], while in (II) the dimer is pseudo-centrosymmetric [O71A···O72B = 2.633 (3) Å and O71B···O72A = 2.634 (3) Å]. In both compounds, the aminium H atoms form direct links to the sulfonate O-atom donors as well as to the water O atom [in (II), four for cation C, five for cation D; in (III), five in total; Tables 2b and 2c]. The water molecule also acts as a bridging donor group in structure extension via the sulfonate groups. The result in both (I) and (II) is the formation of extensive hydrogen-bonded network polymeric structures. An anomalous unexplained feature in the structure of (II) is the presence of some short non-bonding contacts between inversion-related sulfonate O atoms [O51A···O51Avii = 2.815 (3) Å, O52A···O52Aviii = 2.875 (3) Å and O51B···O51Bix = 3.071 (3) Å; symmetry codes: (vii) −x, 1 − y, −z; (viii) 1 − x, 1 − y, −z; (ix) −x, 1 − y, 1 − z].

Experimental top

The title compounds were synthesized by heating under reflux, for 10 min, 1 mmol quantities of 5-SSA and, respectively, 4-fluoroaniline (FAN), 4-chloroaniline (CLAN) and 4-bromoaniline (BRAN) in 50% ethanol/water (50 ml). After concentration to ca 30 ml, partial room-temperature evaporation of the hot-filtered solutions gave violet blocks of (I) (m.p. 517.0–518.5 K) and colourless flat prisms of (II) (m.p. 511.6–513.0 K) and (III) (m.p. 514.2–515.7 K).

Refinement top

H atoms involved in hydrogen-bonding interactions (anilinium, carboxylic, phenol and water) were located by difference methods and their positional and isotropic displacement parameters were refined. Other H atoms were included in the respective refinements at calculated positions (C—H = 0.93 Å) as riding atoms [with Uiso(H) = 1.2Ueq(C)].

Computing details top

For all compounds, data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular conformation and atom-numbering scheme for the FAN+ cation, the 5-SSA anion and the water molecule in (I), showing the cyclic R33(8) hydrogen-bonding association. Non-H atoms are shown as 30% probability displacement ellipsoids. ## Please also check all Figure captions.
[Figure 2] Fig. 2. The atom-numbering scheme for the CLAN+ cations (C and D), the 5-SSA anions (A and B) and the water molecule in (II). Non-H atoms are shown as ??% probability displacement ellipsoids.
[Figure 3] Fig. 3. The molecular conformation and atom-numbering scheme for the BRAN+ cation, the 5-SSA anion and the water molecule in (III). Non-H atoms are shown as ??% probability displacement ellipsoids.
[Figure 4] Fig. 4. Structure extension through hydrogen-bonding interactions (shown as broken lines) in (I), viewed in the unit cell down the b cell direction. H atoms not involved in hydrogen bonding have been omitted for clarity. For symmetry operations see Table 2a. ##If a views is only ## approximately along one direction this should be stated. #
[Figure 5] Fig. 5. Perspective view of the hydrogen-bonding associations in (II) in the unit cell viewed down the a cell direction. For symmetry operations, see Table 2 b.
[Figure 6] Fig. 6. Hydrogen-bonding associations in (III) in the unit cell viewed down the b axis. For symmetry operations, see Table 2c.
(I) 4-fluoroanilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top
Crystal data top
C6H7FN+·C7H5O6S·H2OF(000) = 360
Mr = 347.31Dx = 1.595 Mg m3
Monoclinic, P21Melting point: 517.0–518.5 (dec.) K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.7978 (7) ÅCell parameters from 2628 reflections
b = 12.5513 (12) Åθ = 2.9–27.5°
c = 8.5306 (8) ŵ = 0.27 mm1
β = 96.529 (2)°T = 295 K
V = 723.12 (12) Å3Block, violet
Z = 20.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2275 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ϕ and ω scansh = 87
3741 measured reflectionsk = 1414
2360 independent reflectionsl = 710
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0465P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2360 reflectionsΔρmax = 0.19 e Å3
237 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 1029 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Crystal data top
C6H7FN+·C7H5O6S·H2OV = 723.12 (12) Å3
Mr = 347.31Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.7978 (7) ŵ = 0.27 mm1
b = 12.5513 (12) ÅT = 295 K
c = 8.5306 (8) Å0.30 × 0.30 × 0.20 mm
β = 96.529 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2275 reflections with I > 2σ(I)
3741 measured reflectionsRint = 0.026
2360 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073Δρmax = 0.19 e Å3
S = 1.03Δρmin = 0.22 e Å3
2360 reflectionsAbsolute structure: Flack (1983), 1029 Friedel pairs
237 parametersAbsolute structure parameter: 0.03 (3)
1 restraint
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S50.96121 (7)0.21358 (4)0.44485 (6)0.0276 (2)
O20.8290 (3)0.13345 (14)0.0200 (2)0.0429 (6)
O511.1305 (2)0.17912 (13)0.55238 (18)0.0382 (5)
O520.7843 (2)0.22430 (15)0.52530 (16)0.0363 (5)
O531.0007 (3)0.31023 (13)0.35849 (19)0.0391 (6)
O710.8246 (3)0.18239 (13)0.1704 (2)0.0417 (6)
O720.8297 (3)0.01163 (13)0.24153 (18)0.0439 (6)
C10.8648 (3)0.05471 (17)0.0316 (3)0.0258 (7)
C20.8526 (3)0.05107 (18)0.0815 (3)0.0301 (7)
C30.8631 (3)0.07365 (19)0.2431 (3)0.0350 (8)
C40.8901 (3)0.00675 (18)0.3517 (3)0.0319 (7)
C50.9116 (3)0.11223 (17)0.3019 (3)0.0269 (7)
C60.8986 (3)0.13554 (18)0.1444 (2)0.0265 (6)
C70.8395 (3)0.08030 (18)0.1378 (3)0.0295 (7)
F410.5887 (3)0.55890 (18)0.3366 (2)0.0669 (6)
N110.7149 (3)0.48293 (18)0.3078 (2)0.0412 (7)
C110.6783 (3)0.5042 (2)0.1366 (3)0.0356 (7)
C210.6660 (3)0.4190 (2)0.0348 (3)0.0423 (9)
C310.6357 (4)0.4376 (2)0.1264 (3)0.0464 (9)
C410.6173 (4)0.5401 (2)0.1784 (3)0.0451 (9)
C510.6278 (3)0.6267 (2)0.0776 (3)0.0442 (9)
C610.6589 (3)0.6078 (2)0.0832 (3)0.0399 (8)
O1W0.4444 (4)0.3384 (2)0.3885 (4)0.0733 (10)
H20.821 (4)0.112 (3)0.109 (4)0.053 (10)*
H30.85160.14360.27670.0420*
H40.89410.00850.45870.0380*
H60.91220.20570.11200.0320*
H710.807 (5)0.196 (4)0.262 (5)0.087 (13)*
H11A0.748 (4)0.543 (4)0.359 (4)0.062 (10)*
H11B0.810 (4)0.435 (4)0.327 (4)0.060 (9)*
H11C0.604 (4)0.455 (4)0.340 (4)0.058 (10)*
H210.67790.34970.07350.0510*
H310.62800.38120.19750.0560*
H510.61430.69580.11670.0530*
H610.66650.66420.15420.0480*
H1A0.322 (6)0.333 (3)0.381 (5)0.082 (13)*
H1B0.496 (5)0.294 (4)0.445 (5)0.088 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0385 (3)0.0245 (3)0.0195 (2)0.0000 (2)0.0021 (2)0.0008 (2)
O20.0684 (13)0.0267 (9)0.0322 (11)0.0031 (8)0.0001 (9)0.0056 (8)
O510.0448 (9)0.0378 (10)0.0300 (9)0.0021 (7)0.0049 (7)0.0054 (7)
O520.0454 (9)0.0409 (9)0.0231 (7)0.0074 (8)0.0062 (6)0.0004 (8)
O530.0624 (11)0.0268 (9)0.0290 (9)0.0066 (8)0.0094 (8)0.0013 (7)
O710.0735 (12)0.0321 (10)0.0200 (9)0.0032 (8)0.0073 (8)0.0013 (7)
O720.0717 (11)0.0353 (10)0.0245 (9)0.0011 (8)0.0052 (8)0.0055 (7)
C10.0288 (11)0.0264 (12)0.0223 (11)0.0007 (8)0.0035 (8)0.0009 (9)
C20.0327 (12)0.0275 (12)0.0294 (12)0.0003 (9)0.0011 (10)0.0032 (10)
C30.0469 (14)0.0234 (12)0.0337 (13)0.0031 (10)0.0001 (11)0.0058 (9)
C40.0407 (12)0.0326 (13)0.0220 (11)0.0045 (10)0.0015 (9)0.0054 (9)
C50.0301 (11)0.0255 (12)0.0249 (12)0.0001 (9)0.0019 (9)0.0005 (9)
C60.0316 (10)0.0246 (11)0.0236 (11)0.0006 (9)0.0044 (9)0.0010 (8)
C70.0372 (12)0.0289 (13)0.0227 (11)0.0009 (9)0.0046 (9)0.0028 (9)
F410.0653 (10)0.0938 (14)0.0408 (9)0.0072 (10)0.0028 (8)0.0101 (9)
N110.0420 (12)0.0374 (12)0.0438 (12)0.0050 (9)0.0030 (9)0.0035 (10)
C110.0301 (11)0.0371 (14)0.0388 (13)0.0036 (10)0.0008 (10)0.0038 (10)
C210.0404 (13)0.0315 (14)0.0537 (17)0.0013 (11)0.0003 (12)0.0012 (11)
C310.0419 (15)0.0528 (17)0.0436 (16)0.0018 (12)0.0015 (12)0.0105 (13)
C410.0343 (13)0.0612 (18)0.0388 (15)0.0030 (12)0.0001 (11)0.0064 (13)
C510.0373 (13)0.0433 (16)0.0513 (17)0.0033 (12)0.0016 (11)0.0112 (13)
C610.0364 (12)0.0335 (14)0.0495 (16)0.0035 (10)0.0030 (11)0.0019 (11)
O1W0.0461 (13)0.0627 (17)0.111 (2)0.0001 (11)0.0080 (13)0.0397 (15)
Geometric parameters (Å, º) top
S5—O511.4535 (15)C1—C21.400 (3)
S5—O521.4571 (15)C2—C31.401 (4)
S5—O531.4599 (17)C3—C41.368 (3)
S5—C51.768 (2)C4—C51.403 (3)
F41—C411.362 (3)C5—C61.368 (3)
O2—C21.346 (3)C3—H30.9296
O71—C71.313 (3)C4—H40.9300
O72—C71.232 (3)C6—H60.9307
O2—H20.80 (3)C11—C611.379 (4)
O71—H710.80 (4)C11—C211.374 (4)
O1W—H1B0.79 (5)C21—C311.387 (4)
O1W—H1A0.83 (4)C31—C411.362 (4)
N11—C111.478 (3)C41—C511.383 (4)
N11—H11C0.90 (3)C51—C611.384 (4)
N11—H11A0.89 (5)C21—H210.9306
N11—H11B0.88 (4)C31—H310.9298
C1—C61.399 (3)C51—H510.9300
C1—C71.471 (4)C61—H610.9292
O51—S5—O52111.52 (9)O72—C7—C1122.9 (2)
O51—S5—O53112.82 (10)O71—C7—O72122.3 (2)
O51—S5—C5107.24 (10)O71—C7—C1114.8 (2)
O52—S5—O53111.71 (11)C2—C3—H3119.85
O52—S5—C5106.76 (10)C4—C3—H3119.83
O53—S5—C5106.34 (10)C3—C4—H4119.97
C2—O2—H2110 (3)C5—C4—H4119.93
C7—O71—H71115 (4)C5—C6—H6119.77
H1A—O1W—H1B111 (4)C1—C6—H6119.73
C11—N11—H11B110 (2)N11—C11—C61119.7 (2)
C11—N11—H11C109 (2)N11—C11—C21118.4 (2)
H11A—N11—H11B110 (3)C21—C11—C61121.9 (2)
H11A—N11—H11C111 (3)C11—C21—C31119.2 (2)
H11B—N11—H11C107 (4)C21—C31—C41118.7 (2)
C11—N11—H11A110 (2)F41—C41—C31118.9 (2)
C2—C1—C6119.3 (2)F41—C41—C51118.1 (2)
C2—C1—C7120.1 (2)C31—C41—C51122.9 (2)
C6—C1—C7120.59 (19)C41—C51—C61118.2 (2)
O2—C2—C1122.7 (2)C11—C61—C51119.1 (2)
O2—C2—C3117.8 (2)C11—C21—H21120.44
C1—C2—C3119.5 (2)C31—C21—H21120.41
C2—C3—C4120.3 (2)C41—C31—H31120.69
C3—C4—C5120.1 (2)C21—C31—H31120.64
C4—C5—C6120.1 (2)C41—C51—H51120.93
S5—C5—C6120.63 (17)C61—C51—H51120.86
S5—C5—C4119.23 (19)C11—C61—H61120.45
C1—C6—C5120.5 (2)C51—C61—H61120.41
O51—S5—C5—C451.89 (19)C1—C2—C3—C41.6 (3)
O52—S5—C5—C467.76 (19)C2—C3—C4—C51.3 (3)
O53—S5—C5—C4172.84 (17)C3—C4—C5—C62.3 (3)
O51—S5—C5—C6126.64 (18)C3—C4—C5—S5176.21 (16)
O52—S5—C5—C6113.71 (18)C4—C5—C6—C10.3 (3)
O53—S5—C5—C65.7 (2)S5—C5—C6—C1178.21 (16)
C6—C1—C2—C33.6 (3)N11—C11—C61—C51178.98 (19)
C7—C1—C2—O23.8 (3)C61—C11—C21—C310.8 (3)
C6—C1—C7—O72172.4 (2)N11—C11—C21—C31178.7 (2)
C7—C1—C2—C3175.55 (19)C21—C11—C61—C510.6 (3)
C2—C1—C6—C52.7 (3)C11—C21—C31—C410.6 (4)
C6—C1—C7—O718.8 (3)C21—C31—C41—F41179.6 (2)
C6—C1—C2—O2177.0 (2)C21—C31—C41—C510.1 (4)
C2—C1—C7—O71170.4 (2)C31—C41—C51—C610.2 (4)
C7—C1—C6—C5176.51 (19)F41—C41—C51—C61179.3 (2)
C2—C1—C7—O728.5 (3)C41—C51—C61—C110.1 (3)
O2—C2—C3—C4179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O720.80 (3)1.92 (4)2.625 (2)145 (4)
O1W—H1A···O53i0.83 (4)2.19 (4)3.019 (3)177 (4)
O1W—H1B···O520.79 (5)2.18 (4)2.853 (3)142 (4)
N11—H11A···O51ii0.89 (5)2.01 (5)2.882 (3)168 (3)
N11—H11B···O530.88 (4)2.03 (4)2.910 (3)172 (4)
N11—H11C···O1W0.90 (3)1.90 (4)2.726 (3)152 (4)
O71—H71···O52iii0.80 (4)1.84 (4)2.632 (2)176 (4)
Symmetry codes: (i) x1, y, z; (ii) x+2, y+1/2, z+1; (iii) x, y, z1.
(II) 4-chloroanilinium 3-carboxy-4-hydroxybenzenesulfonate hemihydrate top
Crystal data top
C6H7ClN+·C7H5O6S·0.5H2OF(000) = 1464
Mr = 354.77Dx = 1.576 Mg m3
Monoclinic, P21/cMelting point = 511.6–513.3.0 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.7107 Å
a = 7.455 (4) ÅCell parameters from 3985 reflections
b = 11.849 (7) Åθ = 2.4–27.6°
c = 33.848 (19) ŵ = 0.43 mm1
β = 90.817 (12)°T = 295 K
V = 2990 (3) Å3Block, colourless
Z = 80.45 × 0.30 × 0.15 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
4133 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ϕ and ω scansh = 88
11861 measured reflectionsk = 1410
5220 independent reflectionsl = 3940
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.21 w = 1/[σ2(Fo2) + (0.0713P)2]
where P = (Fo2 + 2Fc2)/3
5220 reflections(Δ/σ)max = 0.009
444 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
C6H7ClN+·C7H5O6S·0.5H2OV = 2990 (3) Å3
Mr = 354.77Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.455 (4) ŵ = 0.43 mm1
b = 11.849 (7) ÅT = 295 K
c = 33.848 (19) Å0.45 × 0.30 × 0.15 mm
β = 90.817 (12)°
Data collection top
Bruker SMART CCD area detector
diffractometer
4133 reflections with I > 2σ(I)
11861 measured reflectionsRint = 0.028
5220 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.21Δρmax = 0.41 e Å3
5220 reflectionsΔρmin = 0.54 e Å3
444 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S5A0.24091 (10)0.42594 (5)0.048951 (16)0.0298 (2)
O2A0.4975 (3)0.69127 (17)0.18525 (5)0.0528 (8)
O51A0.0899 (3)0.49596 (16)0.03683 (5)0.0430 (7)
O52A0.3818 (3)0.42376 (16)0.01997 (5)0.0423 (7)
O53A0.1838 (3)0.31643 (14)0.06214 (5)0.0421 (5)*
O71A0.1948 (3)0.40020 (16)0.20242 (5)0.0501 (8)
O72A0.3446 (3)0.54215 (16)0.23032 (5)0.0475 (8)
C1A0.3432 (4)0.5254 (2)0.16093 (7)0.0299 (9)
C2A0.4406 (4)0.6245 (2)0.15523 (7)0.0333 (9)
C3A0.4810 (4)0.6585 (2)0.11718 (7)0.0380 (10)
C4A0.4266 (4)0.5961 (2)0.08543 (7)0.0335 (9)
C5A0.3305 (4)0.49675 (19)0.09081 (7)0.0270 (8)
C6A0.2897 (4)0.46204 (19)0.12809 (7)0.0276 (8)
C7A0.2949 (4)0.4901 (2)0.20068 (7)0.0350 (9)
S5B0.28878 (10)0.44097 (5)0.456715 (17)0.0298 (2)
O2B0.0095 (3)0.18868 (18)0.32133 (5)0.0549 (8)
O51B0.1495 (3)0.51788 (17)0.46989 (6)0.0497 (8)
O52B0.3311 (3)0.35715 (17)0.48601 (5)0.0536 (8)
O53B0.4447 (3)0.50017 (16)0.44251 (5)0.0409 (7)
O71B0.2983 (3)0.47718 (16)0.30390 (5)0.0466 (8)
O72B0.1474 (3)0.33540 (16)0.27594 (5)0.0478 (8)
C1B0.1618 (4)0.3473 (2)0.34553 (6)0.0290 (9)
C2B0.0571 (4)0.2513 (2)0.35121 (7)0.0346 (9)
C3B0.0184 (4)0.2173 (2)0.38963 (7)0.0374 (10)
C4B0.0862 (4)0.2743 (2)0.42123 (7)0.0340 (9)
C5B0.1936 (4)0.36865 (19)0.41585 (7)0.0272 (8)
C6B0.2292 (4)0.40597 (19)0.37819 (7)0.0277 (8)
C7B0.2027 (4)0.3858 (2)0.30559 (7)0.0336 (9)
Cl4C0.18989 (18)0.46444 (10)0.73684 (2)0.0892 (5)
N1C0.1900 (3)0.41885 (18)0.56285 (6)0.0357 (8)
C1C0.1839 (4)0.4342 (2)0.60556 (7)0.0307 (9)
C2C0.0969 (4)0.3552 (2)0.62791 (8)0.0402 (10)
C3C0.0968 (5)0.3657 (2)0.66835 (8)0.0474 (12)
C4C0.1836 (5)0.4547 (3)0.68580 (8)0.0498 (13)
C5C0.2647 (5)0.5360 (3)0.66353 (9)0.0515 (11)
C6C0.2643 (4)0.5261 (2)0.62290 (8)0.0425 (10)
Cl4D0.35328 (17)0.77313 (9)0.29620 (2)0.0829 (5)
N1D0.2463 (3)0.88873 (18)0.46442 (6)0.0381 (8)
C1D0.2694 (4)0.8581 (2)0.42311 (7)0.0336 (9)
C2D0.3588 (4)0.7606 (2)0.41341 (8)0.0416 (10)
C3D0.3836 (5)0.7348 (2)0.37428 (9)0.0488 (13)
C4D0.3188 (5)0.8056 (3)0.34568 (8)0.0478 (10)
C5D0.2277 (5)0.9020 (3)0.35511 (9)0.0492 (11)
C6D0.2043 (4)0.9286 (2)0.39396 (8)0.0427 (10)
O1W0.2885 (5)0.7015 (2)0.51330 (7)0.0575 (10)
H2A0.473 (7)0.662 (4)0.2061 (16)0.079 (14)*
H3A0.54580.72450.11330.0450*
H4A0.45390.61990.06000.0400*
H6A0.22570.39550.13160.0330*
H71A0.178 (6)0.384 (4)0.2260 (15)0.075 (15)*
H2B0.016 (7)0.218 (4)0.3001 (16)0.082 (15)*
H3B0.05480.15490.39360.0450*
H4B0.06070.24990.44670.0410*
H6B0.29830.47040.37460.0330*
H71B0.302 (7)0.499 (4)0.2812 (15)0.070 (14)*
H2C0.03830.29490.61580.0480*
H3C0.03800.31260.68370.0570*
H5C0.31970.59760.67570.0620*
H6C0.31800.58110.60750.0510*
H11C0.091 (7)0.447 (4)0.5518 (16)0.053 (15)*
H12C0.196 (7)0.345 (4)0.5573 (17)0.063 (15)*
H13C0.285 (6)0.454 (4)0.5531 (16)0.057 (16)*
H2D0.40200.71260.43310.0500*
H3D0.44440.66940.36730.0590*
H5D0.18220.94890.33530.0590*
H6D0.14430.99440.40070.0510*
H11D0.333 (6)0.933 (4)0.4725 (16)0.057 (15)*
H12D0.251 (6)0.827 (4)0.4793 (17)0.061 (16)*
H13D0.140 (6)0.920 (4)0.4676 (16)0.053 (15)*
H1W0.244 (7)0.643 (4)0.4995 (13)0.077 (17)*
H2W0.414 (8)0.685 (4)0.5121 (14)0.120 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S5A0.0280 (5)0.0377 (4)0.0237 (3)0.0082 (3)0.0011 (3)0.0045 (2)
O2A0.0708 (19)0.0506 (12)0.0370 (10)0.0274 (11)0.0009 (11)0.0055 (9)
O51A0.0289 (15)0.0557 (12)0.0439 (10)0.0051 (9)0.0120 (9)0.0124 (9)
O52A0.0352 (15)0.0624 (13)0.0295 (9)0.0103 (9)0.0054 (9)0.0022 (8)
O53A0.0586 (16)0.0357 (10)0.0321 (9)0.0151 (9)0.0027 (9)0.0002 (7)
O71A0.0750 (19)0.0499 (12)0.0253 (9)0.0301 (11)0.0006 (10)0.0020 (8)
O72A0.0648 (18)0.0492 (12)0.0283 (10)0.0192 (10)0.0022 (9)0.0015 (8)
C1A0.0316 (19)0.0301 (13)0.0281 (12)0.0009 (11)0.0010 (11)0.0017 (10)
C2A0.034 (2)0.0320 (14)0.0339 (13)0.0019 (11)0.0030 (12)0.0027 (10)
C3A0.041 (2)0.0307 (14)0.0423 (15)0.0122 (12)0.0020 (13)0.0041 (11)
C4A0.032 (2)0.0366 (14)0.0319 (13)0.0037 (11)0.0011 (12)0.0071 (10)
C5A0.0225 (18)0.0293 (13)0.0291 (12)0.0013 (10)0.0041 (11)0.0029 (9)
C6A0.0254 (17)0.0283 (12)0.0289 (12)0.0022 (10)0.0019 (11)0.0026 (9)
C7A0.038 (2)0.0363 (15)0.0308 (13)0.0010 (12)0.0001 (12)0.0004 (11)
S5B0.0295 (5)0.0355 (4)0.0246 (3)0.0018 (3)0.0023 (3)0.0000 (2)
O2B0.0725 (19)0.0539 (12)0.0382 (11)0.0315 (11)0.0026 (11)0.0050 (9)
O51B0.0342 (16)0.0614 (13)0.0537 (12)0.0045 (9)0.0036 (10)0.0263 (10)
O52B0.0739 (19)0.0529 (12)0.0338 (10)0.0054 (11)0.0112 (10)0.0117 (9)
O53B0.0319 (14)0.0533 (12)0.0377 (10)0.0073 (8)0.0031 (9)0.0033 (8)
O71B0.0647 (18)0.0473 (12)0.0278 (9)0.0223 (10)0.0015 (9)0.0056 (8)
O72B0.0674 (18)0.0479 (11)0.0281 (9)0.0184 (10)0.0042 (9)0.0006 (8)
C1B0.0307 (19)0.0304 (13)0.0258 (12)0.0024 (11)0.0011 (11)0.0018 (9)
C2B0.034 (2)0.0340 (14)0.0358 (13)0.0033 (11)0.0009 (12)0.0026 (10)
C3B0.036 (2)0.0332 (14)0.0432 (15)0.0060 (11)0.0064 (13)0.0044 (11)
C4B0.034 (2)0.0359 (14)0.0322 (13)0.0009 (11)0.0070 (12)0.0070 (10)
C5B0.0242 (18)0.0306 (13)0.0270 (12)0.0046 (10)0.0024 (10)0.0002 (9)
C6B0.0261 (18)0.0264 (12)0.0307 (12)0.0021 (10)0.0003 (11)0.0015 (9)
C7B0.035 (2)0.0350 (14)0.0307 (13)0.0015 (11)0.0019 (12)0.0017 (10)
Cl4C0.1095 (11)0.1205 (9)0.0371 (4)0.0268 (7)0.0118 (5)0.0154 (5)
N1C0.0318 (17)0.0413 (13)0.0339 (11)0.0031 (10)0.0012 (10)0.0010 (9)
C1C0.0257 (19)0.0348 (14)0.0317 (13)0.0072 (11)0.0004 (11)0.0023 (10)
C2C0.046 (2)0.0323 (14)0.0424 (15)0.0022 (12)0.0053 (14)0.0051 (11)
C3C0.059 (3)0.0430 (16)0.0406 (15)0.0078 (14)0.0103 (15)0.0042 (12)
C4C0.052 (3)0.060 (2)0.0374 (15)0.0181 (16)0.0035 (15)0.0068 (14)
C5C0.043 (2)0.0545 (19)0.0569 (18)0.0020 (15)0.0053 (16)0.0240 (15)
C6C0.034 (2)0.0382 (15)0.0553 (17)0.0003 (12)0.0047 (14)0.0047 (12)
Cl4D0.1152 (11)0.0857 (7)0.0482 (5)0.0177 (6)0.0197 (5)0.0067 (4)
N1D0.0293 (17)0.0393 (13)0.0455 (13)0.0020 (10)0.0032 (11)0.0063 (10)
C1D0.0273 (19)0.0325 (14)0.0410 (14)0.0026 (11)0.0001 (12)0.0019 (10)
C2D0.041 (2)0.0353 (15)0.0486 (16)0.0033 (12)0.0006 (14)0.0045 (12)
C3D0.054 (3)0.0348 (15)0.0580 (18)0.0023 (13)0.0121 (16)0.0057 (13)
C4D0.050 (2)0.0488 (17)0.0447 (16)0.0138 (15)0.0067 (15)0.0018 (13)
C5D0.042 (2)0.0532 (18)0.0524 (18)0.0048 (14)0.0038 (15)0.0116 (14)
C6D0.036 (2)0.0359 (15)0.0563 (18)0.0047 (12)0.0001 (15)0.0044 (12)
O1W0.068 (2)0.0478 (15)0.0564 (14)0.0117 (13)0.0104 (13)0.0113 (11)
Geometric parameters (Å, º) top
Cl4C—C4C1.731 (3)C4A—C5A1.391 (4)
Cl4D—C4D1.741 (3)C5A—C6A1.366 (3)
S5A—O53A1.439 (2)C3A—H3A0.9295
S5A—C5A1.769 (3)C4A—H4A0.9310
S5A—O51A1.453 (2)C6A—H6A0.9301
S5A—O52A1.448 (2)C1B—C6B1.394 (3)
S5B—O53B1.446 (2)C1B—C2B1.394 (4)
S5B—O51B1.456 (2)C1B—C7B1.463 (3)
S5B—O52B1.435 (2)C2B—C3B1.395 (3)
S5B—C5B1.767 (3)C3B—C4B1.357 (4)
O2A—C2A1.351 (3)C4B—C5B1.389 (4)
O71A—C7A1.302 (3)C5B—C6B1.379 (3)
O72A—C7A1.230 (3)C3B—H3B0.9299
O2A—H2A0.81 (5)C4B—H4B0.9315
O71A—H71A0.83 (5)C6B—H6B0.9299
O2B—C2B1.344 (3)C1C—C6C1.371 (4)
O71B—C7B1.298 (3)C1C—C2C1.372 (4)
O72B—C7B1.234 (3)C2C—C3C1.374 (4)
O2B—H2B0.82 (5)C3C—C4C1.367 (5)
O71B—H71B0.81 (5)C4C—C5C1.369 (5)
O1W—H2W0.96 (6)C5C—C6C1.380 (4)
O1W—H1W0.90 (5)C2C—H2C0.9297
N1C—C1C1.458 (3)C3C—H3C0.9298
N1C—H11C0.89 (5)C5C—H5C0.9305
N1C—H13C0.89 (5)C6C—H6C0.9288
N1C—H12C0.90 (5)C1D—C6D1.376 (4)
N1D—C1D1.457 (3)C1D—C2D1.376 (4)
N1D—H13D0.88 (5)C2D—C3D1.374 (4)
N1D—H11D0.87 (5)C3D—C4D1.364 (4)
N1D—H12D0.89 (5)C4D—C5D1.369 (5)
C1A—C2A1.395 (4)C5D—C6D1.366 (4)
C1A—C6A1.395 (4)C2D—H2D0.9302
C1A—C7A1.459 (4)C3D—H3D0.9300
C2A—C3A1.387 (3)C5D—H5D0.9311
C3A—C4A1.361 (4)C6D—H6D0.9289
O51A—S5A—O52A112.68 (11)O2B—C2B—C1B123.2 (2)
O51A—S5A—O53A111.79 (13)C1B—C2B—C3B119.2 (2)
O51A—S5A—C5A103.74 (12)C2B—C3B—C4B120.8 (2)
O52A—S5A—O53A114.52 (12)C3B—C4B—C5B120.4 (2)
O52A—S5A—C5A106.37 (13)C4B—C5B—C6B119.9 (2)
O53A—S5A—C5A106.81 (11)S5B—C5B—C6B119.19 (19)
O51B—S5B—C5B105.25 (13)S5B—C5B—C4B120.90 (18)
O51B—S5B—O52B111.85 (12)C1B—C6B—C5B120.1 (2)
O51B—S5B—O53B112.23 (12)O71B—C7B—O72B123.0 (2)
O53B—S5B—C5B106.90 (12)O71B—C7B—C1B115.0 (2)
O52B—S5B—O53B113.30 (13)O72B—C7B—C1B121.9 (2)
O52B—S5B—C5B106.68 (11)C2B—C3B—H3B119.59
C2A—O2A—H2A109 (4)C4B—C3B—H3B119.66
C7A—O71A—H71A109 (3)C3B—C4B—H4B119.77
C2B—O2B—H2B110 (3)C5B—C4B—H4B119.80
C7B—O71B—H71B109 (3)C5B—C6B—H6B119.90
H1W—O1W—H2W100 (4)C1B—C6B—H6B120.00
H11C—N1C—H12C109 (5)N1C—C1C—C2C118.9 (2)
C1C—N1C—H12C109 (4)N1C—C1C—C6C120.3 (2)
H11C—N1C—H13C109 (5)C2C—C1C—C6C120.9 (2)
H12C—N1C—H13C110 (5)C1C—C2C—C3C119.6 (2)
C1C—N1C—H13C110 (3)C2C—C3C—C4C119.5 (3)
C1C—N1C—H11C109 (3)C3C—C4C—C5C121.0 (3)
C1D—N1D—H12D110 (3)Cl4C—C4C—C3C119.2 (2)
C1D—N1D—H11D111 (3)Cl4C—C4C—C5C119.8 (3)
H12D—N1D—H13D108 (4)C4C—C5C—C6C119.6 (3)
C1D—N1D—H13D110 (4)C1C—C6C—C5C119.3 (3)
H11D—N1D—H13D112 (4)C1C—C2C—H2C120.27
H11D—N1D—H12D107 (5)C3C—C2C—H2C120.12
C2A—C1A—C6A119.1 (2)C2C—C3C—H3C120.15
C6A—C1A—C7A120.6 (2)C4C—C3C—H3C120.31
C2A—C1A—C7A120.3 (2)C4C—C5C—H5C120.23
O2A—C2A—C3A117.3 (2)C6C—C5C—H5C120.16
O2A—C2A—C1A123.2 (2)C5C—C6C—H6C120.31
C1A—C2A—C3A119.6 (2)C1C—C6C—H6C120.42
C2A—C3A—C4A120.6 (2)N1D—C1D—C6D119.4 (2)
C3A—C4A—C5A120.3 (2)N1D—C1D—C2D120.2 (2)
S5A—C5A—C6A120.7 (2)C2D—C1D—C6D120.4 (2)
S5A—C5A—C4A119.05 (18)C1D—C2D—C3D119.3 (2)
C4A—C5A—C6A119.8 (2)C2D—C3D—C4D119.7 (3)
C1A—C6A—C5A120.6 (2)Cl4D—C4D—C3D119.4 (3)
O71A—C7A—O72A122.6 (2)Cl4D—C4D—C5D119.3 (2)
O71A—C7A—C1A115.2 (2)C3D—C4D—C5D121.3 (3)
O72A—C7A—C1A122.2 (2)C4D—C5D—C6D119.2 (3)
C2A—C3A—H3A119.73C1D—C6D—C5D120.1 (3)
C4A—C3A—H3A119.67C1D—C2D—H2D120.42
C5A—C4A—H4A119.80C3D—C2D—H2D120.30
C3A—C4A—H4A119.91C4D—C3D—H3D120.07
C1A—C6A—H6A119.73C2D—C3D—H3D120.19
C5A—C6A—H6A119.65C4D—C5D—H5D120.46
C2B—C1B—C6B119.6 (2)C6D—C5D—H5D120.36
C2B—C1B—C7B120.4 (2)C1D—C6D—H6D119.97
C6B—C1B—C7B120.0 (2)C5D—C6D—H6D119.91
O2B—C2B—C3B117.6 (2)
O51A—S5A—C5A—C4A73.8 (3)C2B—C1B—C7B—O71B178.8 (3)
O51A—S5A—C5A—C6A98.9 (2)C2B—C1B—C7B—O72B0.2 (4)
O52A—S5A—C5A—C4A45.3 (3)C6B—C1B—C7B—O71B1.9 (4)
O52A—S5A—C5A—C6A142.0 (2)C6B—C1B—C2B—O2B178.5 (3)
O53A—S5A—C5A—C4A168.0 (2)C7B—C1B—C6B—C5B178.8 (3)
O53A—S5A—C5A—C6A19.3 (3)C6B—C1B—C7B—O72B179.1 (3)
O52B—S5B—C5B—C4B35.0 (3)C1B—C2B—C3B—C4B2.2 (4)
O51B—S5B—C5B—C4B84.0 (2)O2B—C2B—C3B—C4B177.8 (3)
O51B—S5B—C5B—C6B96.9 (2)C2B—C3B—C4B—C5B0.9 (4)
O53B—S5B—C5B—C6B22.6 (3)C3B—C4B—C5B—S5B177.9 (2)
O52B—S5B—C5B—C6B144.1 (2)C3B—C4B—C5B—C6B1.1 (4)
O53B—S5B—C5B—C4B156.5 (2)C4B—C5B—C6B—C1B1.8 (4)
C6A—C1A—C2A—O2A179.8 (2)S5B—C5B—C6B—C1B177.2 (2)
C6A—C1A—C2A—C3A0.5 (4)N1C—C1C—C6C—C5C176.8 (3)
C6A—C1A—C7A—O72A177.7 (3)C2C—C1C—C6C—C5C3.1 (4)
C7A—C1A—C2A—C3A178.2 (3)C6C—C1C—C2C—C3C2.8 (4)
C7A—C1A—C2A—O2A1.1 (4)N1C—C1C—C2C—C3C177.1 (3)
C2A—C1A—C7A—O72A3.6 (4)C1C—C2C—C3C—C4C0.1 (5)
C2A—C1A—C7A—O71A176.0 (3)C2C—C3C—C4C—C5C2.6 (5)
C6A—C1A—C7A—O71A2.7 (4)C2C—C3C—C4C—Cl4C177.6 (3)
C7A—C1A—C6A—C5A178.1 (3)Cl4C—C4C—C5C—C6C178.0 (3)
C2A—C1A—C6A—C5A0.6 (4)C3C—C4C—C5C—C6C2.2 (5)
C1A—C2A—C3A—C4A0.0 (4)C4C—C5C—C6C—C1C0.6 (5)
O2A—C2A—C3A—C4A179.4 (3)N1D—C1D—C6D—C5D178.9 (3)
C2A—C3A—C4A—C5A0.4 (4)C6D—C1D—C2D—C3D0.5 (4)
C3A—C4A—C5A—C6A0.4 (4)N1D—C1D—C2D—C3D178.2 (3)
C3A—C4A—C5A—S5A173.2 (2)C2D—C1D—C6D—C5D0.2 (4)
S5A—C5A—C6A—C1A172.6 (2)C1D—C2D—C3D—C4D0.3 (5)
C4A—C5A—C6A—C1A0.1 (4)C2D—C3D—C4D—Cl4D179.2 (3)
C6B—C1B—C2B—C3B1.5 (4)C2D—C3D—C4D—C5D0.5 (5)
C7B—C1B—C2B—O2B0.8 (4)C3D—C4D—C5D—C6D1.2 (5)
C7B—C1B—C2B—C3B179.2 (3)Cl4D—C4D—C5D—C6D178.5 (3)
C2B—C1B—C6B—C5B0.5 (4)C4D—C5D—C6D—C1D1.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O71A—H71A···O72B0.83 (5)1.80 (5)2.633 (3)175 (5)
O71B—H71B···O72A0.81 (5)1.83 (5)2.634 (3)172 (5)
O1W—H1W···O51B0.90 (5)1.92 (5)2.815 (4)180 (4)
O2A—H2A···O72A0.81 (5)1.90 (5)2.607 (3)145 (5)
O2B—H2B···O72B0.82 (5)1.89 (5)2.608 (3)145 (5)
O1W—H2W···O52Bi0.96 (6)1.96 (6)2.920 (5)175 (4)
N1C—H11C···O51Bii0.89 (5)1.97 (5)2.849 (4)169 (5)
N1D—H11D···O52Aiii0.87 (5)2.14 (4)2.845 (4)137 (4)
N1D—H11D···O52Aiv0.87 (5)2.36 (5)3.072 (3)139 (4)
N1C—H12C···O53Av0.90 (5)1.92 (5)2.788 (3)162 (5)
N1D—H12D···O1W0.89 (5)1.90 (5)2.783 (4)173 (4)
N1C—H13C···O53Bi0.89 (5)2.09 (5)2.896 (4)152 (5)
N1C—H13C···O52B0.89 (5)2.57 (5)2.913 (4)104 (5)
N1D—H13D···O51Avi0.88 (5)1.94 (5)2.810 (4)168 (5)
N1D—H13D···O51Aiv0.88 (5)2.58 (5)3.052 (3)115 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+3/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x, y+1/2, z+1/2.
(III) 4-bromoanilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top
Crystal data top
C6H7BrN+·C7H5O6S·H2ODx = 1.713 Mg m3
Mr = 408.22Melting point = 514.2–515.7 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4362 reflections
a = 12.7810 (19) Åθ = 2.3–27.0°
b = 6.986 (1) ŵ = 2.76 mm1
c = 35.454 (5) ÅT = 295 K
V = 3165.6 (8) Å3Block, colourless
Z = 80.45 × 0.30 × 0.30 mm
F(000) = 1648
Data collection top
Bruker SMART CCD area-detector
diffractometer
2788 independent reflections
Radiation source: sealed tube2203 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1515
Tmin = 0.350, Tmax = 0.436k = 84
14778 measured reflectionsl = 4241
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0657P)2 + 0.9744P]
where P = (Fo2 + 2Fc2)/3
2842 reflections(Δ/σ)max = 0.003
237 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C6H7BrN+·C7H5O6S·H2OV = 3165.6 (8) Å3
Mr = 408.22Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.7810 (19) ŵ = 2.76 mm1
b = 6.986 (1) ÅT = 295 K
c = 35.454 (5) Å0.45 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2788 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2203 reflections with I > 2σ(I)
Tmin = 0.350, Tmax = 0.436Rint = 0.032
14778 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.59 e Å3
2842 reflectionsΔρmin = 0.55 e Å3
237 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S50.47157 (5)0.96199 (10)0.696416 (18)0.0337 (2)
O20.24796 (17)0.7489 (3)0.55712 (6)0.0519 (8)
O510.57779 (17)1.0167 (3)0.68714 (6)0.0519 (8)
O520.41149 (17)1.1239 (3)0.70977 (5)0.0475 (7)
O530.46616 (16)0.7984 (3)0.72161 (5)0.0455 (6)
O710.53666 (17)1.0287 (3)0.55021 (6)0.0504 (8)
O720.40158 (17)0.8994 (3)0.51939 (5)0.0490 (7)
C10.4033 (2)0.8850 (4)0.58601 (7)0.0319 (8)
C20.3054 (2)0.7953 (4)0.58797 (7)0.0340 (8)
C30.2631 (2)0.7498 (4)0.62296 (8)0.0370 (8)
C40.3146 (2)0.7966 (4)0.65550 (7)0.0357 (8)
C50.4118 (2)0.8882 (4)0.65387 (7)0.0295 (8)
C60.4561 (2)0.9302 (3)0.61935 (7)0.0306 (8)
C70.4472 (2)0.9386 (4)0.54897 (8)0.0367 (9)
Br410.86288 (4)1.03786 (7)0.534233 (11)0.0840 (2)
N110.9246 (2)0.9495 (3)0.70380 (7)0.0432 (8)
C110.9090 (2)0.9728 (4)0.66345 (8)0.0375 (8)
C210.8155 (3)1.0409 (5)0.64965 (9)0.0511 (11)
C310.8019 (3)1.0618 (5)0.61127 (10)0.0561 (11)
C410.8822 (3)1.0138 (4)0.58725 (9)0.0505 (10)
C510.9759 (3)0.9469 (4)0.60075 (10)0.0506 (11)
C610.9894 (2)0.9270 (4)0.63919 (9)0.0460 (10)
O1W0.7294 (3)0.8389 (8)0.73346 (11)0.0891 (14)
H20.283 (3)0.784 (6)0.5384 (11)0.069 (13)*
H30.19910.68680.62430.0440*
H40.28500.76730.67880.0430*
H60.52140.98880.61830.0370*
H720.555 (3)1.056 (4)0.5292 (10)0.048 (10)*
H11A0.951 (3)1.059 (4)0.7140 (10)0.068 (11)*
H11B0.970 (3)0.856 (4)0.7080 (10)0.066 (10)*
H11C0.864 (3)0.920 (4)0.7150 (10)0.064 (11)*
H210.76161.07270.66610.0610*
H310.73891.10780.60170.0670*
H511.02970.91540.58420.0610*
H611.05280.88280.64870.0550*
H1A0.708 (4)0.779 (8)0.7487 (18)0.11 (2)*
H1B0.684 (4)0.892 (7)0.7201 (17)0.10 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0443 (4)0.0357 (4)0.0211 (3)0.0017 (3)0.0037 (3)0.0004 (3)
O20.0601 (13)0.0662 (15)0.0293 (11)0.0235 (12)0.0087 (10)0.0016 (10)
O510.0463 (12)0.0726 (15)0.0367 (12)0.0118 (11)0.0091 (9)0.0033 (10)
O520.0673 (14)0.0414 (11)0.0337 (11)0.0092 (10)0.0048 (9)0.0115 (9)
O530.0682 (13)0.0455 (11)0.0228 (9)0.0081 (10)0.0026 (8)0.0069 (8)
O710.0582 (14)0.0701 (15)0.0228 (11)0.0234 (12)0.0074 (9)0.0008 (10)
O720.0586 (12)0.0678 (13)0.0206 (10)0.0136 (11)0.0016 (9)0.0035 (10)
C10.0410 (14)0.0317 (13)0.0230 (13)0.0007 (12)0.0025 (11)0.0005 (11)
C20.0429 (15)0.0325 (14)0.0266 (13)0.0034 (12)0.0042 (11)0.0030 (11)
C30.0388 (14)0.0376 (15)0.0345 (15)0.0103 (12)0.0011 (11)0.0004 (11)
C40.0452 (16)0.0348 (14)0.0271 (13)0.0028 (12)0.0069 (11)0.0029 (11)
C50.0376 (14)0.0273 (12)0.0236 (13)0.0022 (11)0.0007 (10)0.0014 (10)
C60.0356 (14)0.0284 (13)0.0279 (13)0.0002 (11)0.0010 (10)0.0012 (10)
C70.0457 (16)0.0380 (16)0.0265 (14)0.0028 (13)0.0043 (12)0.0056 (11)
Br410.1346 (5)0.0798 (4)0.0375 (3)0.0063 (3)0.0071 (2)0.0017 (2)
N110.0547 (15)0.0372 (13)0.0378 (14)0.0001 (12)0.0040 (11)0.0028 (10)
C110.0467 (16)0.0299 (13)0.0358 (15)0.0036 (13)0.0015 (12)0.0009 (12)
C210.0500 (18)0.058 (2)0.0453 (19)0.0065 (15)0.0051 (14)0.0051 (15)
C310.0553 (19)0.062 (2)0.051 (2)0.0043 (16)0.0072 (16)0.0047 (16)
C410.077 (2)0.0375 (16)0.0371 (17)0.0077 (16)0.0058 (16)0.0025 (13)
C510.062 (2)0.0412 (17)0.0487 (19)0.0014 (15)0.0146 (16)0.0010 (14)
C610.0488 (17)0.0385 (17)0.0506 (19)0.0008 (13)0.0021 (14)0.0000 (14)
O1W0.0653 (19)0.119 (3)0.083 (2)0.005 (2)0.0007 (15)0.045 (3)
Geometric parameters (Å, º) top
Br41—C411.903 (3)C1—C21.401 (4)
S5—O511.448 (2)C2—C31.390 (4)
S5—O531.452 (2)C3—C41.368 (4)
S5—C51.768 (3)C4—C51.399 (4)
S5—O521.447 (2)C5—C61.380 (4)
O2—C21.357 (3)C3—H30.9301
O71—C71.306 (3)C4—H40.9314
O72—C71.231 (3)C6—H60.9303
O2—H20.84 (4)C11—C611.378 (4)
O71—H720.80 (4)C11—C211.376 (5)
O1W—H1B0.84 (5)C21—C311.380 (5)
O1W—H1A0.74 (6)C31—C411.375 (5)
N11—C111.454 (4)C41—C511.372 (5)
N11—H11C0.89 (4)C51—C611.381 (5)
N11—H11A0.91 (3)C21—H210.9296
N11—H11B0.89 (3)C31—H310.9310
C1—C61.397 (4)C51—H510.9303
C1—C71.476 (4)C61—H610.9304
O51—S5—O52111.44 (13)O72—C7—C1121.4 (2)
O51—S5—O53113.08 (12)O71—C7—O72123.4 (3)
O51—S5—C5106.76 (12)O71—C7—C1115.2 (2)
O52—S5—O53112.87 (12)C2—C3—H3119.73
O52—S5—C5106.13 (12)C4—C3—H3119.55
O53—S5—C5105.95 (12)C3—C4—H4120.01
C2—O2—H2106 (3)C5—C4—H4119.87
C7—O71—H72110 (3)C5—C6—H6119.81
H1A—O1W—H1B114 (6)C1—C6—H6119.92
C11—N11—H11B110 (2)N11—C11—C61119.1 (2)
C11—N11—H11C110 (2)N11—C11—C21120.5 (3)
H11A—N11—H11B108 (3)C21—C11—C61120.4 (3)
H11A—N11—H11C110 (3)C11—C21—C31119.8 (3)
H11B—N11—H11C109 (3)C21—C31—C41119.4 (3)
C11—N11—H11A110 (2)Br41—C41—C31119.6 (3)
C2—C1—C6119.4 (2)Br41—C41—C51119.2 (3)
C2—C1—C7119.8 (2)C31—C41—C51121.2 (3)
C6—C1—C7120.8 (2)C41—C51—C61119.2 (3)
O2—C2—C1123.4 (2)C11—C61—C51120.0 (3)
O2—C2—C3117.0 (2)C11—C21—H21120.21
C1—C2—C3119.6 (2)C31—C21—H21120.01
C2—C3—C4120.7 (2)C41—C31—H31120.26
C3—C4—C5120.1 (2)C21—C31—H31120.33
C4—C5—C6119.9 (2)C41—C51—H51120.38
S5—C5—C6121.2 (2)C61—C51—H51120.42
S5—C5—C4118.82 (19)C11—C61—H61120.03
C1—C6—C5120.3 (2)C51—C61—H61120.00
O51—S5—C5—C4169.1 (2)C1—C2—C3—C41.9 (4)
O52—S5—C5—C471.9 (2)C2—C3—C4—C51.1 (4)
O53—S5—C5—C448.3 (3)C3—C4—C5—C60.4 (4)
O51—S5—C5—C615.0 (3)C3—C4—C5—S5175.5 (2)
O52—S5—C5—C6103.9 (2)C4—C5—C6—C11.3 (4)
O53—S5—C5—C6135.8 (2)S5—C5—C6—C1174.5 (2)
C6—C1—C2—C31.1 (4)N11—C11—C61—C51179.6 (3)
C7—C1—C2—O21.8 (4)C61—C11—C21—C310.6 (5)
C6—C1—C7—O72179.9 (2)N11—C11—C21—C31179.9 (3)
C7—C1—C2—C3178.3 (3)C21—C11—C61—C510.9 (4)
C2—C1—C6—C50.5 (4)C11—C21—C31—C410.1 (5)
C6—C1—C7—O710.0 (4)C21—C31—C41—Br41178.8 (3)
C6—C1—C2—O2179.0 (2)C21—C31—C41—C510.5 (5)
C2—C1—C7—O71177.2 (2)C31—C41—C51—C610.2 (4)
C7—C1—C6—C5176.7 (2)Br41—C41—C51—C61179.1 (2)
C2—C1—C7—O723.0 (4)C41—C51—C61—C110.5 (4)
O2—C2—C3—C4178.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O720.84 (4)1.84 (4)2.598 (3)149 (4)
O71—H72···O72i0.80 (4)1.84 (4)2.639 (3)176 (3)
O1W—H1A···O52ii0.74 (6)2.38 (6)3.090 (5)162 (5)
O1W—H1B···O510.84 (5)1.99 (5)2.827 (5)179 (6)
N11—H11A···O53iii0.91 (3)2.00 (3)2.879 (3)162 (3)
N11—H11B···O53iv0.89 (3)2.53 (4)2.897 (3)106 (3)
N11—H11B···O51v0.89 (3)2.56 (3)3.081 (3)119 (3)
N11—H11B···O52v0.89 (3)2.22 (3)3.100 (3)172 (3)
N11—H11C···O1W0.89 (4)1.93 (4)2.815 (5)173 (3)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y1/2, z+3/2; (iii) x+3/2, y+1/2, z; (iv) x+1/2, y, z+3/2; (v) x+3/2, y1/2, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC6H7FN+·C7H5O6S·H2OC6H7ClN+·C7H5O6S·0.5H2OC6H7BrN+·C7H5O6S·H2O
Mr347.31354.77408.22
Crystal system, space groupMonoclinic, P21Monoclinic, P21/cOrthorhombic, Pbca
Temperature (K)295295295
a, b, c (Å)6.7978 (7), 12.5513 (12), 8.5306 (8)7.455 (4), 11.849 (7), 33.848 (19)12.7810 (19), 6.986 (1), 35.454 (5)
α, β, γ (°)90, 96.529 (2), 9090, 90.817 (12), 9090, 90, 90
V3)723.12 (12)2990 (3)3165.6 (8)
Z288
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.270.432.76
Crystal size (mm)0.30 × 0.30 × 0.200.45 × 0.30 × 0.150.45 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.350, 0.436
No. of measured, independent and
observed [I > 2σ(I)] reflections
3741, 2360, 2275 11861, 5220, 4133 14778, 2788, 2203
Rint0.0260.0280.032
(sin θ/λ)max1)0.5950.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.073, 1.03 0.049, 0.132, 1.21 0.038, 0.112, 1.07
No. of reflections236052202842
No. of parameters237444237
No. of restraints100
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.220.41, 0.540.59, 0.55
Absolute structureFlack (1983), 1029 Friedel pairs??
Absolute structure parameter0.03 (3)??

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 1999), SHELXTL (Bruker, 1997), SHELXTL, PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O720.80 (3)1.92 (4)2.625 (2)145 (4)
O1W—H1A···O53i0.83 (4)2.19 (4)3.019 (3)177 (4)
O1W—H1B···O520.79 (5)2.18 (4)2.853 (3)142 (4)
N11—H11A···O51ii0.89 (5)2.01 (5)2.882 (3)168 (3)
N11—H11B···O530.88 (4)2.03 (4)2.910 (3)172 (4)
N11—H11C···O1W0.90 (3)1.90 (4)2.726 (3)152 (4)
O71—H71···O52iii0.80 (4)1.84 (4)2.632 (2)176 (4)
Symmetry codes: (i) x1, y, z; (ii) x+2, y+1/2, z+1; (iii) x, y, z1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O71A—H71A···O72B0.83 (5)1.80 (5)2.633 (3)175 (5)
O71B—H71B···O72A0.81 (5)1.83 (5)2.634 (3)172 (5)
O1W—H1W···O51B0.90 (5)1.92 (5)2.815 (4)180 (4)
O2A—H2A···O72A0.81 (5)1.90 (5)2.607 (3)145 (5)
O2B—H2B···O72B0.82 (5)1.89 (5)2.608 (3)145 (5)
O1W—H2W···O52Bi0.96 (6)1.96 (6)2.920 (5)175 (4)
N1C—H11C···O51Bii0.89 (5)1.97 (5)2.849 (4)169 (5)
N1D—H11D···O52Aiii0.87 (5)2.14 (4)2.845 (4)137 (4)
N1D—H11D···O52Aiv0.87 (5)2.36 (5)3.072 (3)139 (4)
N1C—H12C···O53Av0.90 (5)1.92 (5)2.788 (3)162 (5)
N1D—H12D···O1W0.89 (5)1.90 (5)2.783 (4)173 (4)
N1C—H13C···O53Bi0.89 (5)2.09 (5)2.896 (4)152 (5)
N1C—H13C···O52B0.89 (5)2.57 (5)2.913 (4)104 (5)
N1D—H13D···O51Avi0.88 (5)1.94 (5)2.810 (4)168 (5)
N1D—H13D···O51Aiv0.88 (5)2.58 (5)3.052 (3)115 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+3/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O720.84 (4)1.84 (4)2.598 (3)149 (4)
O71—H72···O72i0.80 (4)1.84 (4)2.639 (3)176 (3)
O1W—H1A···O52ii0.74 (6)2.38 (6)3.090 (5)162 (5)
O1W—H1B···O510.84 (5)1.99 (5)2.827 (5)179 (6)
N11—H11A···O53iii0.91 (3)2.00 (3)2.879 (3)162 (3)
N11—H11B···O53iv0.89 (3)2.53 (4)2.897 (3)106 (3)
N11—H11B···O51v0.89 (3)2.56 (3)3.081 (3)119 (3)
N11—H11B···O52v0.89 (3)2.22 (3)3.100 (3)172 (3)
N11—H11C···O1W0.89 (4)1.93 (4)2.815 (5)173 (3)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y1/2, z+3/2; (iii) x+3/2, y+1/2, z; (iv) x+1/2, y, z+3/2; (v) x+3/2, y1/2, z.
Selected bond lengths and angles (Å, °) for (I), (II)a and (III) top
(I)(II)A,C(II)B,DIII
S5—O511.4535 (15)1.453 (2)1.456 (2)1.448 (2)
S5—O521.4571 (15)1.448 (2)1.435 (2)1.447 (2)
S5—O531.4599 (17)1.439 (2)1.446 (2)1.452 (2)
S5—C51.768 (2)1.769 (3)1.767 (3)1.768 (3)
F41—C41b1.362 (3)1.731 (3)1.741 (3)1.903 (3)
O2—C21.346 (3)1.351 (3)1.344 (3)1.357 (3)
O71—C71.313 (3)1.302 (3)1.298 (3)1.306 (3)
O72—C71.232 (3)1.230 (3)1.234 (3)1.231 (3)
N11—C111.478 (3)1.458 (3)1.457 (3)1.454 (4)
O51—S5—O52111.52 (9)112.68 (11)111.85 (12)111.44 (13)
O51—S5—O53112.82 (10)111.79 (13)112.23 (12)113.08 (12)
O51—S5—C5107.24 (10)103.74 (12)105.25 (13)106.76 (12)
O52—S5—O53111.71 (11)114.52 (12)113.30 (13)112.87 (12)
O52—S5—C5106.76 (10)106.37 (13)106.68 (11)106.13 (12)
O53—S5—C5106.34 (10)106.81 (11)106.90 (12)105.95 (12)
O2—C2—C1122.7 (2)123.2 (2)123.2 (2)123.4 (2)
O2—C2—C3117.8 (2)117.3 (2)117.6 (2)117.0 (2)
S5—C5—C6120.63 (17)120.7 (2)119.19 (19)121.2 (2)
S5—C5—C4119.23 (19)119.05 (18)120.90 (18)118.82 (19)
O72—C7—C1122.9 (2)122.1 (2)121.9 (2)121.4 (2)
O71—C7—O72122.3 (2)122.6 (2)123.0 (2)123.4 (3)
O71—C7—C1114.8 (2)115.2 (2)115.0 (2)115.2 (2)
N11—C11—C61119.7 (2)120.3 (2)119.4 (2)119.1 (2)
N11—C11—C21118.4 (2)118.9 (2)120.2 (2)120.5 (3)
F41—C41—C31118.9 (2)119.2 (2)119.4 (3)119.6 (3)
F41—C41—C51118.1 (2)119.8 (3)119.3 (2)119.2 (3)
O51—S5—C5—C451.89 (19)-73.8 (3)-84.0 (2)169.1 (2)
O52—S5—C5—C4-67.76 (19)45.3 (3)35.0 (3)-71.9 (2)
O53—S5—C5—C4172.84 (17)168.0 (2)156.5 (2)48.3 (3)
O51—S5—C5—C6-126.64 (18)98.9 (2)96.9 (2)-15.0 (3)
O52—S5—C5—C6113.71 (18)-142.0 (2)-144.1 (2)103.9 (2)
O53—S5—C5—C6-5.7 (2)-19.3 (3)-22.6 (3)-135.8 (2)
C2—C1—C7—O71170.4 (2)176.0 (3)178.8 (3)177.2 (2)
C6—C1—C7—O71-8.8 (3)-2.7 (4)-1.9 (4)0.0 (4)
C6—C1—C7—O72172.4 (2)177.7 (3)179.1 (3)179.9 (2)
C2—C1—C7—O72-8.5 (3)-3.6 (4)-0.2 (4)-3.0 (4)
a Data for anion with atom label suffix A and cation with atom label suffix C are in column 3 and data for anion with atom label suffix B and cation with atom label suffix D are in column 4.

b For F41 read Cl4C, Cl4D and Br41 in columns 3, 4 and 5, respectively.
 

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