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The asymmetric unit of the title salt, K+·C6H3BrCl2NO2S·1.5H2O, contains one K+ cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion, one water molecule in general position and one water molecule located on a twofold rotation axis. The K+ cation is hepta-coordinated by three water O atoms and four sulfonyl O atoms from three symmetry-related N-bromo-2,4-dichloro­benzene­sulfonamide anions. The S=N distance of 1.575 (3) Å is consistent with that of a double bond. In the crystal, the anions are linked by O—H...Br and O—H...N hydrogen bonds into layers parallel to the ac plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812042456/nc2295sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536812042456/nc2295Isup2.hkl
Contains datablock I

CCDC reference: 909731

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.093
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.438 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C12 H12 Br2 Cl4 K2 N2 O7 S2 Atom count from _chemical_formula_moiety:C6 H6 Br1 Cl2 K1 N1 O3.5 S1 PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 2 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ ? PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 8.36 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.35 Ratio PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Comment top

The present work was undertaken in order to explore the effect of replacing sodium ion by potassium ion on the solid state structures of metal salts of N-haloarylsulfonamidates (Gowda et al., 2007, 2011a,b). As part of this work, the structure of potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011a), potassium N-bromo-4-chlorobenzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), sodium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (IV) (Gowda et al., 2007) and other sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the title compound, K+ ion is hepta coordinated by three O atoms from water molecules and four sulfonyl O atoms of three different N-bromo-2,4-dichlorobenzenesulfonamide anions. The replacement of Na+ by K+ changes co-ordination from hexa to hepta in the structure (Gowda et al., 2007) and other parameters.

The S—N distance of 1.575 (3) Å is consistent with a S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II), 1.584 (6) Å in (III) and 1.590 (6) Å in (IV).

The asymmetric unit of (I) consists of one potassium cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion and one water molecule in general position and and one water molecule located on a twofold rotation axis.

In the crystal structure the anions are linked by intermolecular O—H···Br and O—H···N hydrogen bonding into layers, that are parallel to the ac plane (Fig. 2 and Table 1).

Related literature top

For preparation of N-haloarylsulfonamides, see: Gowda & Mahadevappa (1983). For studies of the effect of substituents on the structures of N-haloarylsulfonamides, see: George et al. (2000); Gowda et al. (2007, 2011a,b); Olmstead & Power (1986).

Experimental top

The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda & Mahadevappa, 1983). 2 g of 2,4-dichlorobenzenesulfonamide 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-2,4-dichlorobenzenesulfonamide 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 (203–205° C) and estimating, iodometrically, the amount of active bromine present in it. It was further characterized from its infrared spectrum.

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 top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The H atoms bound to O atoms were located in difference map and later restrained to O—H = 0.82 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom.

Computing details top

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).

Figures top
[Figure 1] Fig. 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+. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
Potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate top
Crystal data top
K+·C6H3BrCl2NO2S·1.5H2OF(000) = 1448
Mr = 740.18Dx = 1.975 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2489 reflections
a = 12.5263 (7) Åθ = 3.0–27.7°
b = 6.7638 (4) ŵ = 4.22 mm1
c = 29.703 (2) ÅT = 293 K
β = 98.352 (5)°Prism, yellow
V = 2489.9 (3) Å30.32 × 0.32 × 0.28 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
2535 independent reflections
Radiation source: fine-focus sealed tube2204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Rotation method data acquisition using ω scans.θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1513
Tmin = 0.345, Tmax = 0.384k = 85
4960 measured reflectionsl = 3722
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0429P)2 + 8.3581P]
where P = (Fo2 + 2Fc2)/3
2535 reflections(Δ/σ)max = 0.001
150 parametersΔρmax = 0.76 e Å3
3 restraintsΔρmin = 0.65 e Å3
Crystal data top
K+·C6H3BrCl2NO2S·1.5H2OV = 2489.9 (3) Å3
Mr = 740.18Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.5263 (7) ŵ = 4.22 mm1
b = 6.7638 (4) ÅT = 293 K
c = 29.703 (2) Å0.32 × 0.32 × 0.28 mm
β = 98.352 (5)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
2535 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2204 reflections with I > 2σ(I)
Tmin = 0.345, Tmax = 0.384Rint = 0.014
4960 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0373 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.76 e Å3
2535 reflectionsΔρmin = 0.65 e Å3
150 parameters
Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C10.0780 (3)0.4566 (5)0.11591 (11)0.0271 (7)
C20.1438 (3)0.3775 (5)0.08637 (12)0.0317 (7)
C30.1538 (3)0.4716 (6)0.04598 (12)0.0392 (9)
H30.19800.41920.02640.047*
C40.0974 (3)0.6446 (6)0.03496 (13)0.0426 (9)
C50.0320 (3)0.7248 (6)0.06337 (14)0.0447 (9)
H50.00560.84130.05560.054*
C60.0228 (3)0.6302 (5)0.10361 (13)0.0367 (8)
H60.02140.68410.12300.044*
Br10.11245 (3)0.10625 (6)0.130655 (14)0.04440 (14)
Cl10.21550 (9)0.15999 (15)0.09788 (4)0.0485 (3)
Cl20.10726 (10)0.7571 (2)0.01671 (4)0.0650 (4)
K10.34306 (6)0.13766 (12)0.23492 (3)0.0366 (2)
N10.0277 (2)0.1274 (4)0.16389 (10)0.0319 (6)
O10.1712 (2)0.3416 (4)0.19584 (8)0.0386 (6)
O20.0093 (2)0.4804 (4)0.18845 (8)0.0383 (6)
O30.2037 (2)0.1486 (4)0.19206 (10)0.0426 (6)
H310.234 (3)0.195 (7)0.1725 (12)0.051*
H320.155 (3)0.088 (6)0.1774 (14)0.051*
O40.50000.4277 (6)0.25000.0471 (10)
H410.490 (4)0.502 (6)0.2710 (11)0.056*
S10.06429 (7)0.34987 (12)0.16983 (3)0.02745 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0271 (16)0.0256 (16)0.0280 (16)0.0039 (13)0.0014 (12)0.0003 (13)
C20.0261 (16)0.0319 (18)0.0371 (18)0.0031 (14)0.0042 (14)0.0000 (15)
C30.0350 (19)0.048 (2)0.0364 (19)0.0108 (17)0.0109 (15)0.0008 (17)
C40.040 (2)0.048 (2)0.038 (2)0.0161 (18)0.0006 (16)0.0113 (17)
C50.047 (2)0.036 (2)0.050 (2)0.0043 (18)0.0016 (18)0.0116 (18)
C60.0359 (19)0.0322 (18)0.041 (2)0.0040 (15)0.0036 (15)0.0029 (15)
Br10.0342 (2)0.0494 (3)0.0498 (2)0.00725 (17)0.00672 (16)0.01193 (18)
Cl10.0484 (6)0.0376 (5)0.0645 (7)0.0110 (4)0.0250 (5)0.0029 (5)
Cl20.0592 (7)0.0857 (9)0.0483 (6)0.0170 (6)0.0024 (5)0.0322 (6)
K10.0312 (4)0.0354 (4)0.0423 (4)0.0051 (3)0.0021 (3)0.0034 (3)
N10.0307 (15)0.0279 (15)0.0373 (16)0.0006 (12)0.0060 (12)0.0047 (12)
O10.0373 (14)0.0399 (14)0.0353 (14)0.0026 (11)0.0064 (11)0.0010 (11)
O20.0444 (15)0.0387 (14)0.0339 (13)0.0094 (12)0.0130 (11)0.0046 (11)
O30.0475 (17)0.0380 (15)0.0434 (16)0.0052 (12)0.0099 (13)0.0004 (12)
O40.073 (3)0.031 (2)0.041 (2)0.0000.022 (2)0.000
S10.0302 (4)0.0260 (4)0.0260 (4)0.0028 (3)0.0033 (3)0.0000 (3)
Geometric parameters (Å, º) top
C1—C61.384 (5)K1—O32.788 (3)
C1—C21.395 (5)K1—O1iii2.895 (3)
C1—S11.787 (3)K1—O2iii3.045 (3)
C2—C31.380 (5)K1—S1iii3.4910 (12)
C2—Cl11.732 (4)N1—S11.575 (3)
C3—C41.381 (6)O1—S11.447 (3)
C3—H30.9300O1—K1ii2.895 (3)
C4—C51.370 (6)O2—S11.443 (3)
C4—Cl21.734 (4)O2—K1iv2.683 (2)
C5—C61.375 (5)O2—K1ii3.045 (3)
C5—H50.9300O3—K1iii2.740 (3)
C6—H60.9300O3—H310.802 (19)
Br1—N11.890 (3)O3—H320.808 (19)
K1—O12.675 (3)O4—K1v2.767 (3)
K1—O2i2.683 (2)O4—H410.820 (19)
K1—O3ii2.740 (3)S1—K1ii3.4910 (12)
K1—O42.767 (3)
C6—C1—C2118.5 (3)O3—K1—K1v130.38 (6)
C6—C1—S1118.0 (3)O1iii—K1—K1v90.06 (6)
C2—C1—S1123.4 (3)O2iii—K1—K1v43.27 (5)
C3—C2—C1120.4 (3)S1iii—K1—K1v66.97 (2)
C3—C2—Cl1117.0 (3)O1—K1—K1iii94.01 (7)
C1—C2—Cl1122.6 (3)O2i—K1—K1iii103.41 (6)
C2—C3—C4119.3 (4)O3ii—K1—K1iii93.78 (7)
C2—C3—H3120.4O4—K1—K1iii157.36 (5)
C4—C3—H3120.4O3—K1—K1iii38.92 (6)
C5—C4—C3121.4 (4)O1iii—K1—K1iii38.01 (5)
C5—C4—Cl2119.8 (3)O2iii—K1—K1iii84.35 (5)
C3—C4—Cl2118.8 (3)S1iii—K1—K1iii61.08 (2)
C4—C5—C6118.9 (4)K1v—K1—K1iii120.90 (2)
C4—C5—H5120.5O1—K1—K1ii41.78 (6)
C6—C5—H5120.5O2i—K1—K1ii149.20 (6)
C5—C6—C1121.5 (4)O3ii—K1—K1ii39.74 (6)
C5—C6—H6119.2O4—K1—K1ii78.55 (6)
C1—C6—H6119.2O3—K1—K1ii108.70 (7)
O1—K1—O2i123.54 (8)O1iii—K1—K1ii107.85 (6)
O1—K1—O3ii79.66 (9)O2iii—K1—K1ii117.01 (6)
O2i—K1—O3ii149.20 (9)S1iii—K1—K1ii113.48 (3)
O1—K1—O4102.28 (8)K1v—K1—K1ii120.90 (2)
O2i—K1—O480.66 (7)K1iii—K1—K1ii104.55 (3)
O3ii—K1—O474.11 (7)S1—N1—Br1111.33 (16)
O1—K1—O375.45 (8)S1—O1—K1151.14 (16)
O2i—K1—O385.56 (9)S1—O1—K1ii101.80 (13)
O3ii—K1—O3122.44 (5)K1—O1—K1ii100.21 (8)
O4—K1—O3161.68 (7)S1—O2—K1iv165.01 (16)
O1—K1—O1iii122.42 (5)S1—O2—K1ii95.45 (12)
O2i—K1—O1iii102.09 (8)K1iv—O2—K1ii85.68 (7)
O3ii—K1—O1iii76.13 (8)K1iii—O3—K1101.34 (10)
O4—K1—O1iii119.42 (6)K1iii—O3—H31123 (4)
O3—K1—O1iii75.21 (8)K1—O3—H31106 (4)
O1—K1—O2iii157.55 (8)K1iii—O3—H32117 (4)
O2i—K1—O2iii78.37 (9)K1—O3—H32106 (3)
O3ii—K1—O2iii78.12 (8)H31—O3—H32102 (5)
O4—K1—O2iii74.58 (7)K1—O4—K1v89.71 (12)
O3—K1—O2iii114.43 (8)K1—O4—H41112 (3)
O1iii—K1—O2iii48.19 (7)K1v—O4—H41119 (3)
O1—K1—S1iii142.27 (7)O2—S1—O1114.34 (16)
O2i—K1—S1iii91.31 (6)O2—S1—N1115.83 (16)
O3ii—K1—S1iii74.74 (7)O1—S1—N1104.73 (16)
O4—K1—S1iii96.86 (5)O2—S1—C1104.25 (15)
O3—K1—S1iii95.47 (7)O1—S1—C1107.00 (16)
O1iii—K1—S1iii23.94 (5)N1—S1—C1110.46 (16)
O2iii—K1—S1iii24.30 (5)O2—S1—K1ii60.25 (11)
O1—K1—K1v145.05 (6)O1—S1—K1ii54.26 (11)
O2i—K1—K1v51.05 (6)N1—S1—K1ii132.87 (12)
O3ii—K1—K1v98.18 (7)C1—S1—K1ii115.93 (11)
O4—K1—K1v45.15 (6)
C6—C1—C2—C30.3 (5)S1iii—K1—O3—K1iii26.89 (8)
S1—C1—C2—C3177.6 (3)K1v—K1—O3—K1iii91.14 (10)
C6—C1—C2—Cl1179.3 (3)K1ii—K1—O3—K1iii90.17 (8)
S1—C1—C2—Cl12.9 (4)O1—K1—O4—K1v165.19 (7)
C1—C2—C3—C40.3 (5)O2i—K1—O4—K1v42.70 (6)
Cl1—C2—C3—C4179.3 (3)O3ii—K1—O4—K1v119.46 (7)
C2—C3—C4—C50.1 (6)O3—K1—O4—K1v84.4 (3)
C2—C3—C4—Cl2178.0 (3)O1iii—K1—O4—K1v55.99 (7)
C3—C4—C5—C60.0 (6)O2iii—K1—O4—K1v37.71 (5)
Cl2—C4—C5—C6178.1 (3)S1iii—K1—O4—K1v47.51 (2)
C4—C5—C6—C10.1 (6)K1iii—K1—O4—K1v59.77 (14)
C2—C1—C6—C50.1 (5)K1ii—K1—O4—K1v160.16 (4)
S1—C1—C6—C5177.9 (3)K1iv—O2—S1—O189.2 (6)
O2i—K1—O1—S177.2 (4)K1ii—O2—S1—O14.50 (17)
O3ii—K1—O1—S1124.9 (3)K1iv—O2—S1—N132.8 (7)
O4—K1—O1—S1164.0 (3)K1ii—O2—S1—N1126.44 (14)
O3—K1—O1—S12.7 (3)K1iv—O2—S1—C1154.3 (6)
O1iii—K1—O1—S158.8 (3)K1ii—O2—S1—C1111.99 (12)
O2iii—K1—O1—S1116.7 (3)K1iv—O2—S1—K1ii93.7 (6)
S1iii—K1—O1—S177.2 (4)K1—O1—S1—O2134.2 (3)
K1v—K1—O1—S1145.6 (3)K1ii—O1—S1—O24.81 (18)
K1iii—K1—O1—S131.8 (3)K1—O1—S1—N16.3 (4)
K1ii—K1—O1—S1139.2 (4)K1ii—O1—S1—N1132.65 (13)
O2i—K1—O1—K1ii143.58 (9)K1—O1—S1—C1111.0 (3)
O3ii—K1—O1—K1ii14.32 (8)K1ii—O1—S1—C1110.07 (14)
O4—K1—O1—K1ii56.74 (8)K1—O1—S1—K1ii139.0 (4)
O3—K1—O1—K1ii141.96 (10)Br1—N1—S1—O252.7 (2)
O1iii—K1—O1—K1ii80.46 (13)Br1—N1—S1—O1179.61 (16)
O2iii—K1—O1—K1ii22.6 (2)Br1—N1—S1—C165.5 (2)
S1iii—K1—O1—K1ii62.01 (13)Br1—N1—S1—K1ii125.06 (12)
K1v—K1—O1—K1ii75.18 (13)C6—C1—S1—O21.3 (3)
K1iii—K1—O1—K1ii107.44 (7)C2—C1—S1—O2179.2 (3)
O1—K1—O3—K1iii115.86 (10)C6—C1—S1—O1120.2 (3)
O2i—K1—O3—K1iii117.79 (9)C2—C1—S1—O157.7 (3)
O3ii—K1—O3—K1iii48.49 (13)C6—C1—S1—N1126.4 (3)
O4—K1—O3—K1iii159.0 (2)C2—C1—S1—N155.8 (3)
O1iii—K1—O3—K1iii14.03 (8)C6—C1—S1—K1ii62.2 (3)
O2iii—K1—O3—K1iii42.71 (11)C2—C1—S1—K1ii115.6 (3)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x1/2, y+1/2, z; (v) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···Br1i0.80 (2)2.78 (2)3.550 (3)160 (4)
O3—H32···N10.81 (2)2.15 (3)2.917 (4)158 (5)
O4—H41···N1ii0.82 (2)2.16 (2)2.957 (3)165 (5)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaK+·C6H3BrCl2NO2S·1.5H2O
Mr740.18
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)12.5263 (7), 6.7638 (4), 29.703 (2)
β (°) 98.352 (5)
V3)2489.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)4.22
Crystal size (mm)0.32 × 0.32 × 0.28
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.345, 0.384
No. of measured, independent and
observed [I > 2σ(I)] reflections
4960, 2535, 2204
Rint0.014
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.093, 1.09
No. of reflections2535
No. of parameters150
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.76, 0.65

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···Br1i0.802 (19)2.78 (2)3.550 (3)160 (4)
O3—H32···N10.808 (19)2.15 (3)2.917 (4)158 (5)
O4—H41···N1ii0.820 (19)2.16 (2)2.957 (3)165 (5)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z+1/2.
 

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