Potassium 4-nitro­phenyl­sulfonate monohydrate

Blatch, A.J.; Howard, J.A.K.; Probert, M.R.; Smethurst, C.A.; Whiting, A.

doi:10.1107/S1600536806007835

metal-organic compounds

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ISSN: 2056-9890

Volume 62| Part 4| April 2006| Pages m741-m743

https://doi.org/10.1107/S1600536806007835

Potassium 4-nitrophenylsulfonate monohydrate

Alexandrea J. Blatch,^a Judith A. K. Howard,^a Michael R. Probert,^a Christian A. Smethurst ^b and Andrew Whiting ^a ^*

^aDepartment of Chemistry, University of Durham, South Road, Durham DH1 3LE, England, and ^bGlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, England
^*Correspondence e-mail: a.s.batsanov@durham.ac.uk

(Received 19 February 2006; accepted 3 March 2006; online 10 March 2006)

The title compound, K⁺·C₆H₄NO₅S⁻·H₂O, forms a three-dimensional polymeric structure with an O₈ coordination environment of the K⁺ cation.

Comment

As part of a programme aimed at developing new aza-Baeyer–Villiger reactions, we have examined the use of N-alkyl-O-arylsulfonylhydroxylamines as potential nitrene equivalents (Hoffman & Buntain, 1988 ; Hoffman & Salvador, 1989a , 1991 ). Attempts have therefore been made to prepare a range of N-alkyl-O-arylsulfonylhydroxylamines p-XC₆H₄SO₂NHR by reacting RNH₂ with sulfonyl peroxides p-XC₆H₄SO₂OOSO₂C₆H₄-p-X, which in turn are accessible from sulfonyl chlorides p-XC₆H₄SO₂Cl by reaction with t-BuOOH (Hoffman & Cadena, 1977 ; Hoffman & Belfoure, 1983 ; Hoffman & Salvador, 1989b ). The title compound, (I), was isolated as a by-product during this synthesis.

Numerous esters of 4-nitrophenylsulfonic acid have been structurally characterized, as well as some salts with organic cations (Russell et al., 1994 ; Chan & Wong, 2002 ; Tamura et al., 2002 ). However, no salt or complex of any metal with this anion has been studied previously.

(I) has a three-dimensional polymeric (catena) crystal structure (Fig. 1). The asymmetric unit comprises one formula unit. The potassium cation is coordinated by eight O atoms, viz. five from the sulfonate groups of four different anions, one from a nitro group of another anion, and two μ₂-bridging water molecules. The coordination polyhedron can be described as a distorted monocapped pentagonal bipyramid. The anion links five K⁺ cations, four of them via one O atom each. There is only one case of chelation, the sulfonate atoms O1 and O2 coordinated to the same potassium ion, and even this one is highly asymmmetric. The K—O2 distance is 0.33 Å longer than K—O1 and is by far the longest in the structure.

The aqua bridge is highly asymmetric: the K—O distances differ by 0.176 Å and the stronger-bound potassium ion is practically coplanar with the H₂O plane. The weakly coordinated O2 atom and the uncoordinated O5 atom of the nitro group act as acceptors of hydrogen bonds donated by the water molecules. Notwithstanding these differences, both N—O bond lengths are equal within experimental error (mean 1.233 (3) Å), as are the three S—O bond lengths (mean 1.453 (3) Å). The benzene ring and the nitro group of the anion form a dihedral angle of 11.2 (1)°, whereas the S—O2 bond is nearly coplanar with the ring: the dihedral angle C2—C1—S—O2 is 9.0 (3)°.

Figure 1
The environment of a K⁺ cation in the structure of (I)

(50% displacement ellipsoids). [Symmetry codes: (i) 1 − x, 1 − y, 1 − z, (ii) 1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z, (iii) −x, 1 − y, 1 − z, (iv) x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z, (v) 1 − x, y − $[{1\over 2}]$ , $[{3\over 2}]$ − z.]

Experimental

4-Nitrobenzenesulfonyl peroxide p-O₂NC₆H₄SO₂OOSO₂C₆H₄NO₂-p (II) was prepared according to Dannley et al. (1970 ). To a solution of K₂CO₃ (5.10 g, 36.9 mmol) in water (76 ml), ethanol (38 ml) and hydrogen peroxide (35%, 8.75 g) at 253 K a cooled (253 K) solution of 4-nitrobenzenesulfonyl chloride (7.88 g, 35.6 mmol) in chloroform (10 ml) was added and the suspension was mixed at full power for 1 min using a Breville Classique^TM blender. Ethanol (80 ml) was added and the solution was mixed for 4 min at low power. The precipitate formed was filtered off, washed with distilled water and recrystallized from acetone to give (II) as a yellow solid (2.22 g, 31%). The filtrate was cooled at 253 K for 24 h, yielding (I) as yellow crystals (0.160 g, 1.2%), m.p. >593 K, IR, ν, cm⁻¹: 3065 (CH aromatic stretch), 1529 (NO₂), 1461 (SO₂) 819 (p-disubstituted aromatic). ¹H NMR (200 MHz, CDCl₃): 8.20 (d, 2H, CH aromatic, J 8.6 Hz), 8.49 (d, 2H, CH aromatic, J = 8.4 Hz). ¹³C NMR (100 MHz, CDCl3): 123.5 (2 × PhCNO₂), 126.0 (4 × CH aromatic), 140.0 (4 × CH aromatic), 148.0 (2 × PhCSO₂). The properties of (I) agree with those reported by Kozlov & Davydov (1965 ) or Dietze et al. (1989 ).

Crystal data

K⁺·C₆H₄NO₅S⁻·H₂O
M_r = 259.28
Monoclinic, P 2₁ /c
a = 10.794 (1) Å
b = 7.1516 (6) Å
c = 12.417 (1) Å
β = 106.15 (1)°
V = 920.70 (14) Å³
Z = 4
D_x = 1.871 Mg m⁻³
Mo Kα radiation
Cell parameters from 2733 reflections
θ = 3.3–27.5°
μ = 0.81 mm⁻¹
T = 120 (2) K
Block, yellow
0.3 × 0.2 × 0.15 mm

Data collection

Siemens SMART 1K CCD area detector diffractometer
ω scans
Absorption correction: none
9859 measured reflections
2117 independent reflections
1596 reflections with I > 2σ(I)
R_int = 0.067
θ_max = 27.5°
h = −14 → 13
k = −9 → 9
l = −16 → 15

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.095
S = 1.05
2117 reflections
144 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0364P)² + 0.9635P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

K—O1ⁱ	2.712 (2)
K—O3ⁱⁱ	2.765 (2)
K—O3	2.775 (2)
K—O6	2.779 (2)
K—O4ⁱⁱⁱ	2.802 (2)
K—O1^iv	2.819 (2)
K—O6^v	2.955 (3)
K—O2^iv	3.148 (2)

O1ⁱ—K—O3ⁱⁱ	87.93 (6)
O1ⁱ—K—O3	78.99 (6)
O3ⁱⁱ—K—O3	151.04 (3)
O1ⁱ—K—O6	66.46 (7)
O3ⁱⁱ—K—O6	81.82 (7)
O3—K—O6	115.27 (7)
O1ⁱ—K—O4ⁱⁱⁱ	128.10 (7)
O3ⁱⁱ—K—O4ⁱⁱⁱ	134.60 (7)
O3—K—O4ⁱⁱⁱ	71.80 (7)
O6—K—O4ⁱⁱⁱ	88.53 (7)
O1ⁱ—K—O1^iv	146.95 (5)
O3ⁱⁱ—K—O1^iv	91.85 (6)
O3—K—O1^iv	85.63 (6)
O6—K—O1^iv	146.11 (7)
O4ⁱⁱⁱ—K—O1^iv	72.37 (6)
O1ⁱ—K—O6^v	85.46 (7)
O3ⁱⁱ—K—O6^v	74.70 (7)
O3—K—O6^v	78.56 (7)
O6—K—O6^v	143.93 (7)
O4ⁱⁱⁱ—K—O6^v	127.38 (7)
O1^iv—K—O6^v	62.76 (7)
O1ⁱ—K—O2^iv	156.06 (6)
O3ⁱⁱ—K—O2^iv	70.29 (6)
O3—K—O2^iv	124.93 (6)
O6—K—O2^iv	99.66 (7)
O4ⁱⁱⁱ—K—O2^iv	67.84 (6)
O1^iv—K—O2^iv	47.52 (6)
O6^v—K—O2^iv	97.73 (7)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H01⋯O2^vi	0.78 (4)	2.15 (4)	2.922 (3)	172 (4)
O6—H02⋯O5^vii	0.85 (4)	2.23 (4)	3.050 (3)	161 (4)
Symmetry codes: (vi) x, y+1, z; (vii) -x, -y+2, -z+1.

Water atoms H01 and H02 were located in a difference map and refined isotropically. Benzene H atoms were treated as riding on the C atoms, C—H 0.95 Å, U_iso(H) = 1.2U_eq(C).

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806007835/kp2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806007835/kp2006Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Potassium 4-nitrophenylsulfonate monohydrate top

Crystal data top

K⁺·C₆H₄NO₅S⁻·H₂O	F(000) = 528
M_r = 259.28	D_x = 1.871 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2733 reflections
a = 10.794 (1) Å	θ = 3.3–27.5°
b = 7.1516 (6) Å	µ = 0.81 mm⁻¹
c = 12.417 (1) Å	T = 120 K
β = 106.15 (1)°	Block, colourless
V = 920.70 (14) Å³	0.3 × 0.2 × 0.15 mm
Z = 4

Data collection top

Siemens SMART 1K CCD area detector diffractometer	1596 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
Detector resolution: 8 pixels mm^-1	h = −14→13
ω scans	k = −9→9
9859 measured reflections	l = −16→15
2117 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0364P)² + 0.9635P] where P = (F_o² + 2F_c²)/3
2117 reflections	(Δ/σ)_max < 0.001
144 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Special details top

Experimental. The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering 0.3° in ω. Crystal to detector distance 4.51 cm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
K	0.43521 (6)	0.53657 (9)	0.74392 (5)	0.01343 (16)
S	0.37624 (7)	0.22064 (10)	0.46669 (6)	0.01054 (17)
O1	0.4524 (2)	0.2686 (3)	0.39107 (17)	0.0140 (5)
O2	0.3285 (2)	0.0291 (3)	0.45242 (18)	0.0159 (5)
O3	0.4386 (2)	0.2697 (3)	0.58251 (17)	0.0149 (5)
O4	−0.1962 (2)	0.6461 (3)	0.31470 (18)	0.0192 (5)
O5	−0.0704 (2)	0.8883 (3)	0.35935 (18)	0.0188 (5)
O6	0.3076 (2)	0.8669 (3)	0.6626 (2)	0.0207 (5)
H01	0.315 (4)	0.900 (5)	0.605 (3)	0.026 (11)*
H02	0.252 (4)	0.945 (6)	0.672 (3)	0.039 (12)*
N	−0.0886 (2)	0.7181 (4)	0.3463 (2)	0.0147 (5)
C1	0.2366 (3)	0.3660 (4)	0.4267 (2)	0.0108 (6)
C2	0.1131 (3)	0.2881 (4)	0.4060 (2)	0.0132 (6)
H2	0.1032	0.1568	0.4118	0.016*
C3	0.0058 (3)	0.4025 (4)	0.3772 (2)	0.0136 (6)
H3	−0.0787	0.3518	0.3622	0.016*
C4	0.0250 (3)	0.5950 (4)	0.3708 (2)	0.0122 (6)
C5	0.1463 (3)	0.6745 (4)	0.3908 (2)	0.0144 (6)
H5	0.1559	0.8060	0.3859	0.017*
C6	0.2534 (3)	0.5582 (4)	0.4183 (2)	0.0139 (6)
H6	0.3376	0.6092	0.4312	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K	0.0157 (3)	0.0116 (3)	0.0132 (3)	−0.0007 (3)	0.0043 (2)	0.0000 (2)
S	0.0110 (4)	0.0094 (3)	0.0109 (4)	0.0007 (3)	0.0023 (3)	−0.0001 (3)
O1	0.0159 (11)	0.0149 (11)	0.0126 (11)	0.0009 (8)	0.0063 (9)	0.0003 (8)
O2	0.0161 (11)	0.0095 (10)	0.0212 (12)	0.0010 (9)	0.0036 (9)	0.0014 (9)
O3	0.0169 (11)	0.0159 (11)	0.0097 (10)	0.0022 (9)	0.0000 (8)	−0.0016 (8)
O4	0.0121 (12)	0.0241 (12)	0.0207 (12)	−0.0035 (9)	0.0032 (9)	0.0018 (9)
O5	0.0191 (12)	0.0150 (11)	0.0217 (12)	0.0042 (9)	0.0046 (10)	0.0011 (9)
O6	0.0237 (14)	0.0214 (13)	0.0197 (13)	0.0069 (10)	0.0106 (11)	0.0055 (10)
N	0.0137 (14)	0.0205 (14)	0.0107 (13)	0.0018 (11)	0.0047 (10)	0.0033 (10)
C1	0.0109 (14)	0.0142 (15)	0.0061 (14)	−0.0007 (12)	0.0003 (11)	−0.0015 (11)
C2	0.0177 (16)	0.0117 (14)	0.0110 (14)	−0.0015 (12)	0.0055 (12)	−0.0023 (11)
C3	0.0127 (15)	0.0168 (15)	0.0115 (15)	−0.0049 (12)	0.0039 (12)	−0.0005 (11)
C4	0.0126 (15)	0.0154 (15)	0.0070 (14)	0.0023 (12)	0.0002 (11)	0.0002 (11)
C5	0.0175 (16)	0.0120 (14)	0.0137 (15)	0.0002 (12)	0.0045 (12)	−0.0010 (11)
C6	0.0129 (15)	0.0164 (16)	0.0128 (15)	0.0002 (12)	0.0041 (12)	0.0009 (11)

Geometric parameters (Å, º) top

K—O1ⁱ	2.712 (2)	O6—H01	0.78 (4)
K—O3ⁱⁱ	2.765 (2)	O6—H02	0.85 (4)
K—O3	2.775 (2)	N—C4	1.471 (4)
K—O6	2.779 (2)	C1—C6	1.395 (4)
K—O4ⁱⁱⁱ	2.802 (2)	C1—C2	1.401 (4)
K—O1^iv	2.819 (2)	C2—C3	1.382 (4)
K—O6^v	2.955 (3)	C2—H2	0.9500
K—O2^iv	3.148 (2)	C3—C4	1.398 (4)
S—O1	1.451 (2)	C3—H3	0.9500
S—O3	1.451 (2)	C4—C5	1.384 (4)
S—O2	1.457 (2)	C5—C6	1.388 (4)
S—C1	1.784 (3)	C5—H5	0.9500
O4—N	1.230 (3)	C6—H6	0.9500
O5—N	1.236 (3)

O1ⁱ—K—O3ⁱⁱ	87.93 (6)	S—O1—K^vi	106.82 (10)
O1ⁱ—K—O3	78.99 (6)	Kⁱ—O1—K^vi	87.55 (6)
O3ⁱⁱ—K—O3	151.04 (3)	S—O2—K^vi	92.42 (10)
O1ⁱ—K—O6	66.46 (7)	S—O3—K^v	128.22 (11)
O3ⁱⁱ—K—O6	81.82 (7)	S—O3—K	141.86 (12)
O3—K—O6	115.27 (7)	K^v—O3—K	87.38 (6)
O1ⁱ—K—O4ⁱⁱⁱ	128.10 (7)	N—O4—Kⁱⁱⁱ	175.69 (19)
O3ⁱⁱ—K—O4ⁱⁱⁱ	134.60 (7)	K—O6—Kⁱⁱ	83.67 (7)
O3—K—O4ⁱⁱⁱ	71.80 (7)	K—O6—H01	115 (3)
O6—K—O4ⁱⁱⁱ	88.53 (7)	Kⁱⁱ—O6—H01	85 (3)
O1ⁱ—K—O1^iv	146.95 (5)	K—O6—H02	144 (3)
O3ⁱⁱ—K—O1^iv	91.85 (6)	Kⁱⁱ—O6—H02	108 (3)
O3—K—O1^iv	85.63 (6)	H01—O6—H02	100 (4)
O6—K—O1^iv	146.11 (7)	O4—N—O5	123.7 (3)
O4ⁱⁱⁱ—K—O1^iv	72.37 (6)	O4—N—C4	118.3 (2)
O1ⁱ—K—O6^v	85.46 (7)	O5—N—C4	118.0 (2)
O3ⁱⁱ—K—O6^v	74.70 (7)	C6—C1—C2	121.0 (3)
O3—K—O6^v	78.56 (7)	C6—C1—S	118.5 (2)
O6—K—O6^v	143.93 (7)	C2—C1—S	120.4 (2)
O4ⁱⁱⁱ—K—O6^v	127.38 (7)	C3—C2—C1	119.9 (3)
O1^iv—K—O6^v	62.76 (7)	C3—C2—H2	120.0
O1ⁱ—K—O2^iv	156.06 (6)	C1—C2—H2	120.0
O3ⁱⁱ—K—O2^iv	70.29 (6)	C2—C3—C4	118.1 (3)
O3—K—O2^iv	124.93 (6)	C2—C3—H3	121.0
O6—K—O2^iv	99.66 (7)	C4—C3—H3	121.0
O4ⁱⁱⁱ—K—O2^iv	67.84 (6)	C5—C4—C3	122.8 (3)
O1^iv—K—O2^iv	47.52 (6)	C5—C4—N	118.9 (3)
O6^v—K—O2^iv	97.73 (7)	C3—C4—N	118.2 (3)
O1—S—O3	113.22 (12)	C4—C5—C6	118.7 (3)
O1—S—O2	112.87 (12)	C4—C5—H5	120.7
O3—S—O2	113.49 (13)	C6—C5—H5	120.7
O1—S—C1	105.61 (13)	C5—C6—C1	119.5 (3)
O3—S—C1	104.94 (12)	C5—C6—H6	120.3
O2—S—C1	105.73 (13)	C1—C6—H6	120.3
S—O1—Kⁱ	162.38 (12)

C2—C1—S—O2	9.0 (3)	C5—C4—N—O5	−9.6 (4)
C3—C4—N—O4	−11.6 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, −y+1, −z+1; (iv) x, −y+1/2, z+1/2; (v) −x+1, y−1/2, −z+3/2; (vi) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H01···O2^vii	0.78 (4)	2.15 (4)	2.922 (3)	172 (4)
O6—H02···O5^viii	0.85 (4)	2.23 (4)	3.050 (3)	161 (4)

Symmetry codes: (vii) x, y+1, z; (viii) −x, −y+2, −z+1.

Acknowledgements

We thank both the EPSRC and GlaxoSmithKline Pharmaceuticals for a CASE award (to AJB).

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