Potassium N-bromo-2-nitro­benzene­sulfonamidate monohydrate

Abstract

In the title compound, K(+)·C(6)H(4)BrN(2)O(4)S(-)·H(2)O, the K(+) ion is hepta-coordinated by two O atoms from two different water mol-ecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzene-sulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzene-sulfonamidate anions. The S-N distance of 1.576 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by inter-molecular O-H⋯N and O-H⋯Br hydrogen bonds which link the molecules into polymeric layers running parallel to the bc plane.

Full text

Potassium N-bromo-2-nitrobenzene-
sulfonamidate monohydrate
B. Thimme Gowda,
a
* Sabine Foro
b
and H. S. Spandana
a
a
Department of Chemistry, Mangalore University, Mangalagangotri 574 199,
Mangalore, India, and
b
Institute of Materials Science, Darmstadt University of
Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com
Received 4 October 2012; accepted 8 October 2012
Key indicators: single-crystal X-ray study; T= 293 K; mean (C–C) = 0.007 A
˚;
Rfactor = 0.053; wR factor = 0.145; data-to-parameter ratio = 14.7.
In the title compound, K
+
C
6
H
4
BrN
2
O
4
S

H
2
O, the K
+
ion is
hepta-coordinated by two O atoms from two different water
molecules, three sulfonyl O atoms from three N-bromo-2-
nitro-benzenesulfonamidate anions and two nitro O atoms
from two N-bromo-2-nitro-benzenesulfonamidate anions. The
S—N distance of 1.576 (4) A
˚is consistent with an S N
double bond. The crystal structure is stabilized by inter-
molecular O—HN and O—HBr hydrogen bonds which
link the molecules into polymeric layers running parallel to
the bc plane.
Related literature
For the preparation of metal salts of N-haloarylsulfonamides,
see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).
For studies on the effect of substituents and metal ions on the
structures of N-haloarylsulfonamides, see: George et al.
(2000); Gowda et al. (2011a,b); Olmstead & Power (1986). For
positioning of water H atoms, see: Nardelli (1999).
Experimental
Crystal data
K
+
C
6
H
4
BrN
2
O
4
S

H
2
OM
r
= 337.20
Monoclinic, P21=c
a= 13.034 (2) A
˚
b= 12.815 (2) A
˚
c= 6.7741 (9) A
˚
= 100.65 (1)
V= 1112.0 (3) A
˚
3
Z=4
Mo Kradiation
= 4.27 mm
1
T= 293 K
0.48 0.48 0.24 mm
Data collection
Oxford Diffraction Xcalibur
diffractometer with Sapphire
CCD detector
Absorption correction: multi-scan
(CrysAlis RED; Oxford
Diffraction, 2009)
T
min
= 0.234, T
max
= 0.428
3896 measured reflections
2236 independent reflections
1847 reflections with I>2(I)
R
int
= 0.042
Refinement
R[F
2
>2(F
2
)] = 0.053
wR(F
2
) = 0.145
S= 1.06
2236 reflections
152 parameters
3 restraints
H atoms treated by a mixture of
independent and constrained
refinement

max
= 0.79 e A
˚
3

min
=1.21 e A
˚
3
Table 1
Hydrogen-bond geometry (A
˚,).
D—HAD—H HADAD—HA
O5—H51N1
i
0.84 (2) 2.13 (3) 2.926 (5) 157 (5)
O5—H52Br1
ii
0.84 (2) 2.85 (4) 3.509 (4) 137 (4)
Symmetry codes: (i) x;y;zþ1; (ii) x;yþ1
2;zþ3
2.
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford
Diffraction, 2009); program(s) used to solve structure: SHELXS97
(Sheldrick, 2008); program(s) used to refine structure: SHELXL97
(Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); soft-
ware used to prepare material for publication: SHELXL97.
BTG thanks the University Grants Commission, Govern-
ment of India, New Delhi, for a one-time grant to Faculty/
Professors under UGC–BSR.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: ZL2509).
References
George, E., Vivekanandan, S. & Sivakumar, K. (2000). Acta Cryst. C56, 1208–
1209.
Gowda, B. T., Foro, S. & Shakuntala, K. (2011a). Acta Cryst. E67, m926.
Gowda, B. T., Foro, S. & Shakuntala, K. (2011b). Acta Cryst. E67, m1015.
Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta,30, 359–362.
Nardelli, M. (1999). J. Appl. Cryst. 32, 563–571.
Olmstead, M. M. & Power, P. P. (1986). Inorg. Chem. 25, 4057–4058.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford
Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359.
metal-organic compounds
m1358 Gowda et al. doi:10.1107/S1600536812042080 Acta Cryst. (2012). E68, m1358
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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Acta Cryst. (2012). E68, m1358
supplementary materials
Acta Cryst. (2012). E68, m1358 [doi:10.1107/S1600536812042080]
Potassium N-bromo-2-nitrobenzenesulfonamidate monohydrate
B. Thimme Gowda, Sabine Foro and H. S. Spandana
Comment
In the present work, to explore the effect of substituents on the crystal structures of metal salts of N-haloaryl-
sulfonamidates (George et al., 2000; Gowda et al., 2011a,b; Olmstead & Power, 1986), the crystal structure of potassium
N-bromo-2-nitro-benzenesulfonamidate monohydrate (I) has been determined (Fig. 1). The structure of (I) resembles
those of potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011a), potassium N-
bromo-2-methyl-benzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), and sodium N-chloro-aryl-
sulfonamidates (George et al., 2000; Olmstead & Power, 1986).
In the title compound (I), the K+ ion is hepta coordinated by two O atoms from two different water molecules, three
sulfonyl O atoms from three N-bromo-2-nitro-benzenesulfonamidate anions and two nitro O atoms from two N-bromo-2-
nitro-benzenesulfonamidate anions (Fig 2.). This is in contrast to K+ ion hepta coordination by three O atoms from water
molecules and by four sulfonyl O atoms of three N-bromo-2-chloro-benzenesulfonamide anions in (II) and three N-
bromo-2-methyl-benzenesulfonamide anions in (III).
The S—N distance of 1.576 (4) Å in (I) is consistent with an S—N double bond and is in agreement with the observed
values of 1.582 (4) Å in (II) and 1.577 (5) Å in (III).
The packing diagram consists of a two-dimensional polymeric layer running parallel to the bc plane (Fig. 2). The
molecular packing is stabilized by O5—H51···N1 and O5—H52···Br1 hydrogen bonds (Table 1).
Experimental
The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda &
Mahadevappa, 1983) and Usha & Gowda (Usha & Gowda, 2006). 2 g of 2-nitrobenzenesulfonamide was dissolved with
stirring in 40 ml of 5M KOH at room temperature. The resultant solution was cooled in ice and 4 ml of liquid bromine
was added drop wise with constant stirring. The resultant potassium salt of N-bromo-2-nitro-benzenesulfonamidate
monohydrate was filtered under suction, washed quickly with a minimum quantity of ice cold water. The purity of the
compound was checked by determining its melting point (175–177°C) and estimating, iodometrically, the amount of
active bromine present in it. It was further characterized from its infrared spectrum. The characteristic absorptions
observed are 3624.3, 3333.0, 3192.2, 2978.1, 2922.2, 2075.4, 1626.0, 1602.9, 1477.5, 1452.4, 1242.2, 1122.6, 1060.9,
937.4, 817.8, 686.7, 640.4, 578.6, 549.6, 524.6 and 470.6 cm-1.
Prism like yellow single crystals of the title compound used in the X-ray diffraction studies were obtained from its
aqueous solution at room temperature.
Refinement
H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å.
The O-bound H atoms were located in a difference map and were refined with restrained geometry (Nardelli, 1999), viz.

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Acta Cryst. (2012). E68, m1358
O—H distances were restrained to 0.85 (2) Å and the H—H distance was restrained to 1.365 Å, thus leading to the angle
of 107°. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom. The residual
electron-density features are located in the region of Br1. The highest peak and the deepest hole are 0.80 and 0.84 Å from
Br1, respectivily.
Computing details
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009);
data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick,
2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009);
software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Figure 1
Molecular structure of the title compound, showing the atom labelling scheme for the asymmetric unit and extended to
show the coordination geometry for the K+ ion. The displacement ellipsoids are drawn at the 50% probability level. The
H atoms are represented as small spheres of arbitrary radii.

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Acta Cryst. (2012). E68, m1358
Figure 2
Bridging of potassium cations, N-bromo-2-nitro-benzenesulfonamidate anions and water molecules in the structure of the
title compound.

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Acta Cryst. (2012). E68, m1358
Figure 3
Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
Potassium N-bromo-2-nitrobenzenesulfonamidate monohydrate
Crystal data
K+·C6H4BrN2O4S−·H2O
Mr = 337.20
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 13.034 (2) Å
b = 12.815 (2) Å
c = 6.7741 (9) Å
β = 100.65 (1)°
V = 1112.0 (3) Å3
Z = 4
F(000) = 664
Dx = 2.014 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2399 reflections
θ = 3.1–27.8°
µ = 4.27 mm−1
T = 293 K
Prism, yellow
0.48 × 0.48 × 0.24 mm
Data collection
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Radiation source: fine-focus sealed tube
Graphite monochromator
Rotation method data acquisition using ω scans.
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin = 0.234, Tmax = 0.428
3896 measured reflections
2236 independent reflections
1847 reflections with I > 2σ(I)

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Acta Cryst. (2012). E68, m1358
Rint = 0.042
θmax = 26.4°, θmin = 3.2°
h = −16→12
k = −16→11
l = −6→8
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.053
wR(F2) = 0.145
S = 1.06
2236 reflections
152 parameters
3 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0909P)2 + 0.1082P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002
Δρmax = 0.79 e Å−3
Δρmin = −1.21 e Å−3
Extinction correction: SHELXL97 (Sheldrick,
2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.082 (5)
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)
xy z U
iso*/Ueq
C1 0.2873 (3) −0.0123 (3) 0.3340 (6) 0.0272 (9)
C2 0.3529 (3) 0.0693 (3) 0.3079 (6) 0.0271 (8)
C3 0.4505 (3) 0.0546 (4) 0.2573 (6) 0.0346 (10)
H3 0.4930 0.1113 0.2430 0.042*
C4 0.4833 (4) −0.0463 (4) 0.2286 (7) 0.0419 (11)
H4 0.5488 −0.0583 0.1975 0.050*
C5 0.4173 (4) −0.1291 (4) 0.2469 (7) 0.0425 (11)
H5 0.4377 −0.1966 0.2221 0.051*
C6 0.3214 (4) −0.1127 (3) 0.3015 (7) 0.0368 (10)
H6 0.2791 −0.1695 0.3167 0.044*
Br1 0.24804 (4) −0.10055 (4) 0.78959 (7) 0.0470 (3)
K1 0.09562 (9) 0.13045 (8) 0.88211 (15) 0.0418 (3)
N1 0.1510 (3) −0.1035 (3) 0.5411 (6) 0.0384 (9)
N2 0.3214 (3) 0.1792 (3) 0.3257 (5) 0.0316 (8)
O1 0.1685 (3) 0.0941 (2) 0.5295 (5) 0.0395 (8)
O2 0.0840 (3) −0.0085 (2) 0.2371 (5) 0.0442 (8)
O3 0.2363 (3) 0.2061 (3) 0.2308 (5) 0.0454 (8)
O4 0.3826 (3) 0.2369 (3) 0.4304 (6) 0.0520 (9)
S1 0.16307 (8) −0.00155 (7) 0.41728 (15) 0.0294 (3)
O5 −0.0180 (3) 0.2758 (3) 0.6363 (6) 0.0494 (9)
H51 −0.066 (3) 0.240 (3) 0.566 (7) 0.059*

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Acta Cryst. (2012). E68, m1358
H52 −0.044 (4) 0.326 (3) 0.689 (8) 0.059*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.027 (2) 0.0276 (19) 0.0253 (18) 0.0017 (17) 0.0016 (16) −0.0018 (16)
C2 0.026 (2) 0.0279 (18) 0.0271 (18) 0.0015 (17) 0.0053 (16) 0.0028 (16)
C3 0.032 (2) 0.042 (2) 0.032 (2) 0.000 (2) 0.0101 (18) 0.0059 (19)
C4 0.036 (3) 0.054 (3) 0.038 (2) 0.014 (2) 0.015 (2) 0.001 (2)
C5 0.047 (3) 0.036 (2) 0.045 (3) 0.020 (2) 0.012 (2) −0.003 (2)
C6 0.041 (3) 0.030 (2) 0.040 (2) 0.0028 (19) 0.009 (2) −0.0020 (18)
Br1 0.0516 (4) 0.0461 (4) 0.0432 (4) −0.0034 (2) 0.0087 (2) 0.0096 (2)
K1 0.0378 (6) 0.0498 (6) 0.0380 (5) 0.0041 (5) 0.0076 (4) −0.0024 (5)
N1 0.036 (2) 0.034 (2) 0.047 (2) −0.0106 (16) 0.0122 (19) 0.0010 (16)
N2 0.032 (2) 0.0279 (17) 0.0369 (18) −0.0005 (15) 0.0100 (16) 0.0052 (15)
O1 0.046 (2) 0.0313 (15) 0.0463 (18) −0.0007 (13) 0.0206 (16) −0.0100 (13)
O2 0.0293 (17) 0.0527 (19) 0.0465 (18) −0.0035 (15) −0.0039 (15) −0.0014 (16)
O3 0.045 (2) 0.0325 (17) 0.0564 (19) 0.0096 (15) 0.0025 (16) 0.0113 (15)
O4 0.048 (2) 0.0379 (17) 0.070 (2) −0.0146 (16) 0.0112 (19) −0.0130 (17)
S1 0.0254 (6) 0.0274 (5) 0.0360 (5) −0.0033 (4) 0.0069 (4) −0.0032 (4)
O5 0.043 (2) 0.0443 (19) 0.063 (2) −0.0011 (16) 0.0146 (18) 0.0010 (17)
Geometric parameters (Å, º)
C1—C2 1.383 (6) K1—O2ii 2.806 (3)
C1—C6 1.391 (5) K1—O3iii 2.877 (4)
C1—S1 1.815 (4) K1—O2iii 3.018 (4)
C2—C3 1.390 (6) K1—O3i3.081 (4)
C2—N2 1.479 (5) K1—H51 3.06 (5)
C3—C4 1.386 (6) N1—S1 1.576 (4)
C3—H3 0.9300 N2—O4 1.215 (5)
C4—C5 1.385 (7) N2—O3 1.225 (5)
C4—H4 0.9300 O1—S1 1.437 (3)
C5—C6 1.384 (7) O2—S1 1.448 (3)
C5—H5 0.9300 O2—K1ii 2.806 (3)
C6—H6 0.9300 O2—K1iv 3.018 (4)
Br1—N1 1.910 (4) O3—K1iv 2.877 (4)
Br1—K1 3.6829 (12) O3—K1v3.081 (4)
K1—O5 2.743 (4) O5—K1v2.746 (4)
K1—O5i2.746 (4) O5—H51 0.844 (19)
K1—O1 2.768 (3) O5—H52 0.841 (19)
C2—C1—C6 117.1 (4) O2iii—K1—O3i141.88 (10)
C2—C1—S1 126.2 (3) O5—K1—Br1 133.65 (9)
C6—C1—S1 116.7 (3) O5i—K1—Br1 145.95 (9)
C1—C2—C3 123.0 (4) O1—K1—Br1 55.66 (7)
C1—C2—N2 121.5 (4) O2ii—K1—Br1 87.19 (8)
C3—C2—N2 115.4 (4) O3iii—K1—Br1 97.38 (7)
C4—C3—C2 118.7 (4) O2iii—K1—Br1 76.67 (7)
C4—C3—H3 120.6 O3i—K1—Br1 96.72 (7)

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Acta Cryst. (2012). E68, m1358
C2—C3—H3 120.6 O5—K1—H51 15.6 (6)
C5—C4—C3 119.3 (4) O5i—K1—H51 81.7 (9)
C5—C4—H4 120.4 O1—K1—H51 77.0 (10)
C3—C4—H4 120.4 O2ii—K1—H51 68.0 (7)
C6—C5—C4 120.9 (4) O3iii—K1—H51 132.2 (6)
C6—C5—H5 119.5 O2iii—K1—H51 134.5 (10)
C4—C5—H5 119.5 O3i—K1—H51 80.1 (8)
C5—C6—C1 120.9 (4) Br1—K1—H51 125.1 (8)
C5—C6—H6 119.5 S1—N1—Br1 109.8 (2)
C1—C6—H6 119.5 O4—N2—O3 124.7 (4)
N1—Br1—K1 82.87 (12) O4—N2—C2 117.7 (4)
O5—K1—O5i77.92 (8) O3—N2—C2 117.6 (3)
O5—K1—O1 79.82 (11) S1—O1—K1 127.53 (18)
O5i—K1—O1 157.72 (11) S1—O2—K1ii 134.68 (19)
O5—K1—O2ii 82.86 (11) S1—O2—K1iv 120.16 (18)
O5i—K1—O2ii 84.62 (11) K1ii—O2—K1iv 105.16 (10)
O1—K1—O2ii 93.37 (11) N2—O3—K1iv 135.6 (3)
O5—K1—O3iii 117.39 (11) N2—O3—K1v123.6 (3)
O5i—K1—O3iii 70.94 (11) K1iv—O3—K1v100.02 (11)
O1—K1—O3iii 119.80 (11) O1—S1—O2 117.1 (2)
O2ii—K1—O3iii 142.64 (11) O1—S1—N1 115.2 (2)
O5—K1—O2iii 141.57 (11) O2—S1—N1 105.8 (2)
O5i—K1—O2iii 69.28 (11) O1—S1—C1 105.67 (19)
O1—K1—O2iii 131.59 (10) O2—S1—C1 105.7 (2)
O2ii—K1—O2iii 74.84 (10) N1—S1—C1 106.5 (2)
O3iii—K1—O2iii 70.30 (9) K1—O5—K1v112.63 (13)
O5—K1—O3i67.90 (10) K1—O5—H51 104 (4)
O5i—K1—O3i109.52 (11) K1v—O5—H51 108 (4)
O1—K1—O3i60.50 (9) K1—O5—H52 118 (4)
O2ii—K1—O3i143.02 (10) K1v—O5—H52 104 (4)
O3iii—K1—O3i73.50 (8) H51—O5—H52 110 (3)
C6—C1—C2—C3 −1.9 (6) O4—N2—O3—K1iv 156.5 (3)
S1—C1—C2—C3 175.3 (3) C2—N2—O3—K1iv −22.1 (5)
C6—C1—C2—N2 176.0 (4) O4—N2—O3—K1v−35.7 (5)
S1—C1—C2—N2 −6.8 (6) C2—N2—O3—K1v145.7 (3)
C1—C2—C3—C4 1.0 (6) K1—O1—S1—O2 102.7 (3)
N2—C2—C3—C4 −177.0 (4) K1—O1—S1—N1 −22.6 (3)
C2—C3—C4—C5 1.3 (7) K1—O1—S1—C1 −139.9 (2)
C3—C4—C5—C6 −2.8 (7) K1ii—O2—S1—O1 −114.6 (3)
C4—C5—C6—C1 1.8 (8) K1iv—O2—S1—O1 65.8 (3)
C2—C1—C6—C5 0.5 (7) K1ii—O2—S1—N1 15.4 (3)
S1—C1—C6—C5 −177.0 (4) K1iv—O2—S1—N1 −164.3 (2)
N1—Br1—K1—O5 −28.49 (17) K1ii—O2—S1—C1 128.1 (3)
N1—Br1—K1—O5i124.97 (19) K1iv—O2—S1—C1 −51.6 (2)
N1—Br1—K1—O1 −47.15 (14) Br1—N1—S1—O1 −46.5 (3)
N1—Br1—K1—O2ii 48.87 (14) Br1—N1—S1—O2 −177.5 (2)
N1—Br1—K1—O3iii −168.38 (14) Br1—N1—S1—C1 70.3 (2)
N1—Br1—K1—O2iii 123.95 (13) C2—C1—S1—O1 −24.4 (4)

supplementary materials
sup-8
Acta Cryst. (2012). E68, m1358
N1—Br1—K1—O3i−94.22 (13) C6—C1—S1—O1 152.8 (3)
K1—Br1—N1—S1 63.0 (2) C2—C1—S1—O2 100.4 (4)
C1—C2—N2—O4 131.2 (4) C6—C1—S1—O2 −82.4 (4)
C3—C2—N2—O4 −50.8 (5) C2—C1—S1—N1 −147.4 (4)
C1—C2—N2—O3 −50.2 (5) C6—C1—S1—N1 29.8 (4)
C3—C2—N2—O3 127.9 (4) O5i—K1—O5—K1v140.66 (16)
O5—K1—O1—S1 −120.6 (3) O1—K1—O5—K1v−38.60 (13)
O5i—K1—O1—S1 −122.5 (3) O2ii—K1—O5—K1v−133.34 (15)
O2ii—K1—O1—S1 −38.5 (3) O3iii—K1—O5—K1v79.80 (16)
O3iii—K1—O1—S1 123.5 (2) O2iii—K1—O5—K1v172.23 (12)
O2iii—K1—O1—S1 34.2 (3) O3i—K1—O5—K1v23.55 (11)
O3i—K1—O1—S1 169.1 (3) Br1—K1—O5—K1v−54.17 (18)
Br1—K1—O1—S1 45.8 (2)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y, −z+1; (iii) x, y, z+1; (iv) x, y, z−1; (v) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º)
D—H···AD—H H···AD···AD—H···A
O5—H51···N1ii 0.84 (2) 2.13 (3) 2.926 (5) 157 (5)
O5—H52···Br1vi 0.84 (2) 2.85 (4) 3.509 (4) 137 (4)
Symmetry codes: (ii) −x, −y, −z+1; (vi) −x, y+1/2, −z+3/2.