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Acta Cryst. (2007). E63, o4312-o4313
https://doi.org/10.1107/S1600536807049446
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Hydrogen-bonding patterns in 4-[(5-methyl­isoxazol-3-yl)amino­sulfon­yl]anilinium chloride

A. Subashini, P. T. Muthiah, G. Bocelli and A. Cantoni
In the title compound, C10H12O3N3S+·Cl−, 4-amino-N-(5-methyl-3-isoxazol­yl)benzene­sulfonamide is protonated on the amine N atom which is connected to the benzene ring. The geometry around the S atom is considerably distorted from ideal tetra­hedral geometry. The crystal packing is stabilized by inter­molecular N—H...N, N—H...Cl, N—H...O and C—H...O hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049446/bt2536sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049446/bt2536Isup2.hkl
Contains datablock I

CCDC reference: 667353

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.071
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5


Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           29.99
           From the CIF: _reflns_number_total               2021
           Count of symmetry unique reflns         1932
           Completeness (_total/calc)            104.61%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        89
           Fraction of Friedel pairs measured     0.046
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Sulfonamides constitute an important class of antimicrobical agents. The drug, 4-amino-N-(5-methyl-3-isoxzolyl) benzene sulfonamide [Sulfamethoxazole (SMZ)] prevents the formation of dihydrofolic acid, a compound that bacteria must be able to make in order to survive. The two polymorphs of SMZ (Bettinetti et al., 1982) have already been reported in literature.

An ORTEPII (Johnson, 1976) view of the title compound (I), is shown in Fig.1. The asymmetric unit contains one 4-ammonio-N-(5-methyl-3-isoxazolyl) benzene sulfonamide cation and a chloride anion. The cation is protonated on the amine nitrogen (N4) atom. The distances around the S atom in the SMZ molecule agree well with the corresponding distances in other sulfonamides. The atoms around the sulfonamide S atom in (I) are arranged in a slightly distorted tetrahedral configuration. The largest deviation is in the angle O1—S1—O2 [120.92 (17)°], but it confirms to the non-tetrahedral nature commonly observed in sulfonamides (Chatterjee et al., 1982; Haridas et al., 1984; Ghosh et al., 1991; Kendi et al., 2000; Takasuka & Nakai, 2001; Özbey et al., 2005). The S1—C1 distance of 1.775 (3) Å (I) is a normal single-bond value and matches well with those observed in other sulfonamides (Singh et al., 1984; Abramenko & Sergienko, 2002). In the present structure the dihedral angle between the isoxazole and ammonio phenyl plane is found to be 58.0 (2)°, whereas in neutral SMZ structures the dihedral angles are 73.15° for form 1 and 79.66° for form 2 (Bettinetti et al., 1982) respectively. The two torsion angles τ1 (C—C—S—N) and τ2 (C—S—N—C) defining the conformation of the sulfonamide group are reported to lie in the range 70–120° and 60–90°, respectively (Kálmán et al., 1981). The torsion angles τ1 is 73.2 (3)° (C6—C1—S1—N7) and τ2 is -71.2 (3) Å (C1—S1—N7—C8). In the neutral forms, the torsion angles τ1 are -76.59° (Form 1) and -78.55° (Form 2). The torsion angles τ2 are -56.14° in form 1 and -61.58° in form 2. The cations and chloride anions are involved in a network of intermolecular hydrogen bonds, resulting in the formation of infinite chains propagating in the -b direction (Fig. 2). The chloride anion participates in N—H···Cl hydrogen-bond formation as a three proton acceptor, interacting with both the ammonio and amide NH groups [N—Cl = 3.093 (3)–3.177 (3) Å]. The amide N—H group also acts as a donor to the oxygen atom of isoxazole moiety, with an N—O distance of 3.204 (4) Å. The sulfonyl O atom (O1) is involved in a weak interaction with C6 of the phenyl ring through C—H···O hydrogen bonds (Fig 3).

Related literature top

For related literature, see: Abramenko & Sergienko (2002); Bettinetti et al. (1982); Chatterjee et al. (1982); Ghosh et al. (1991); Haridas et al. (1984); Johnson (1976); Kálmán et al. (1981); Kendi et al. (2000); Özbey et al. (2005); Singh et al. (1984); Takasuka & Nakai (2001).

Experimental top

2 ml of HCl (20%) was added slowly to a solution of 4-amino-N-(5-methyl-3-isoxazolyl) benzene sulfonamide in hot ethanol. After a few days, colourless crystals of the title compound (I), were appeared.

Refinement top

All H atoms were placed in idealized locations and were refined using a riding model, with C—H = 0.93 Å, N—H = 0.86–0.92 Å and Uiso(H) = 1.2Ueq (C,N).

Structure description top

Sulfonamides constitute an important class of antimicrobical agents. The drug, 4-amino-N-(5-methyl-3-isoxzolyl) benzene sulfonamide [Sulfamethoxazole (SMZ)] prevents the formation of dihydrofolic acid, a compound that bacteria must be able to make in order to survive. The two polymorphs of SMZ (Bettinetti et al., 1982) have already been reported in literature.

An ORTEPII (Johnson, 1976) view of the title compound (I), is shown in Fig.1. The asymmetric unit contains one 4-ammonio-N-(5-methyl-3-isoxazolyl) benzene sulfonamide cation and a chloride anion. The cation is protonated on the amine nitrogen (N4) atom. The distances around the S atom in the SMZ molecule agree well with the corresponding distances in other sulfonamides. The atoms around the sulfonamide S atom in (I) are arranged in a slightly distorted tetrahedral configuration. The largest deviation is in the angle O1—S1—O2 [120.92 (17)°], but it confirms to the non-tetrahedral nature commonly observed in sulfonamides (Chatterjee et al., 1982; Haridas et al., 1984; Ghosh et al., 1991; Kendi et al., 2000; Takasuka & Nakai, 2001; Özbey et al., 2005). The S1—C1 distance of 1.775 (3) Å (I) is a normal single-bond value and matches well with those observed in other sulfonamides (Singh et al., 1984; Abramenko & Sergienko, 2002). In the present structure the dihedral angle between the isoxazole and ammonio phenyl plane is found to be 58.0 (2)°, whereas in neutral SMZ structures the dihedral angles are 73.15° for form 1 and 79.66° for form 2 (Bettinetti et al., 1982) respectively. The two torsion angles τ1 (C—C—S—N) and τ2 (C—S—N—C) defining the conformation of the sulfonamide group are reported to lie in the range 70–120° and 60–90°, respectively (Kálmán et al., 1981). The torsion angles τ1 is 73.2 (3)° (C6—C1—S1—N7) and τ2 is -71.2 (3) Å (C1—S1—N7—C8). In the neutral forms, the torsion angles τ1 are -76.59° (Form 1) and -78.55° (Form 2). The torsion angles τ2 are -56.14° in form 1 and -61.58° in form 2. The cations and chloride anions are involved in a network of intermolecular hydrogen bonds, resulting in the formation of infinite chains propagating in the -b direction (Fig. 2). The chloride anion participates in N—H···Cl hydrogen-bond formation as a three proton acceptor, interacting with both the ammonio and amide NH groups [N—Cl = 3.093 (3)–3.177 (3) Å]. The amide N—H group also acts as a donor to the oxygen atom of isoxazole moiety, with an N—O distance of 3.204 (4) Å. The sulfonyl O atom (O1) is involved in a weak interaction with C6 of the phenyl ring through C—H···O hydrogen bonds (Fig 3).

For related literature, see: Abramenko & Sergienko (2002); Bettinetti et al. (1982); Chatterjee et al. (1982); Ghosh et al. (1991); Haridas et al. (1984); Johnson (1976); Kálmán et al. (1981); Kendi et al. (2000); Özbey et al. (2005); Singh et al. (1984); Takasuka & Nakai (2001).

Computing details top

Data collection: FEBO (Belletti, 1996); cell refinement: MolEN (Fair, 1990); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the asymmetric unit of (I) showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Hydrogen bonding patterns in compound (I). Symmetry codes: (i) x - 1/2,y + 1/2,z; (ii) x - 1,-y + 1,z - 1/2; (iii) x - 1,y,z.
[Figure 3] Fig. 3. A view of C—H···O interaction in compound (I). Symmetry codes: (v) x - 1/2,-y + 1/2,z - 1/2.
4-[(5-methylisoxazol-3-yl)aminosulfonyl]anilinium chloride top
Crystal data top
C10H12N3O3S+·Cl−F(000) = 600
Mr = 289.75Dx = 1.461 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 25 reflections
a = 8.677 (2) Åθ = 3.0–30.0°
b = 15.615 (3) ŵ = 0.45 mm−1
c = 10.435 (2) ÅT = 293 K
β = 111.29 (2)°Prism, colourless
V = 1317.4 (5) Å30.15 × 0.14 × 0.13 mm
Z = 4
Data collection top
Philips PW 1100
diffractometer		Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 3.4°
Graphite monochromatorh = −12→11
ω scansk = 0→21
2021 measured reflectionsl = 0→14
2021 independent reflections1 standard reflections every 100 reflections
1318 reflections with I > 2σ(I) intensity decay: none
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0282P)2],
where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max < 0.001
2021 reflectionsΔρmax = 0.19 e Å−3
167 parametersΔρmin = −0.21 e Å−3
2 restraintsAbsolute structure: Flack (1983), 89 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.05 (7)
Crystal data top
C10H12N3O3S+·Cl−V = 1317.4 (5) Å3
Mr = 289.75Z = 4
Monoclinic, CcMo Kα radiation
a = 8.677 (2) ŵ = 0.45 mm−1
b = 15.615 (3) ÅT = 293 K
c = 10.435 (2) Å0.15 × 0.14 × 0.13 mm
β = 111.29 (2)°
Data collection top
Philips PW 1100
diffractometer		Rint = 0.000
2021 measured reflections1 standard reflections every 100 reflections
2021 independent reflections intensity decay: none
1318 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.071Δρmax = 0.19 e Å−3
S = 0.90Δρmin = −0.21 e Å−3
2021 reflectionsAbsolute structure: Flack (1983), 89 Friedel pairs
167 parametersAbsolute structure parameter: −0.05 (7)
2 restraints
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

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2> σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.33023 (10)0.30198 (5)1.02704 (8)0.0452 (3)
O10.4305 (3)0.32910 (17)1.1625 (2)0.0622 (10)
O20.2677 (3)0.21625 (14)1.0016 (3)0.0592 (10)
O30.3264 (3)0.21386 (15)0.6159 (3)0.0564 (10)
N4−0.2378 (3)0.54615 (16)0.8049 (3)0.0418 (10)
N70.4442 (3)0.31761 (16)0.9346 (3)0.0436 (9)
N80.3621 (4)0.21322 (17)0.7594 (3)0.0525 (11)
C10.1613 (4)0.3740 (2)0.9626 (3)0.0384 (10)
C20.1549 (5)0.4471 (2)1.0364 (4)0.0501 (11)
C30.0266 (5)0.5039 (2)0.9840 (4)0.0514 (14)
C4−0.0967 (4)0.48678 (19)0.8594 (3)0.0370 (10)
C5−0.0929 (4)0.4144 (2)0.7853 (3)0.0438 (11)
C60.0384 (4)0.3578 (2)0.8374 (3)0.0443 (11)
C80.3984 (4)0.29307 (19)0.7974 (3)0.0351 (10)
C90.3927 (4)0.3457 (2)0.6865 (4)0.0451 (11)
C100.3460 (4)0.2944 (2)0.5764 (4)0.0459 (12)
C110.3117 (5)0.3066 (3)0.4289 (4)0.0645 (16)
Cl10.56666 (11)0.50480 (6)0.99302 (10)0.0488 (3)
H20.237600.457601.121300.0600*
H30.022900.553501.032100.0620*
H4A−0.197900.600400.800700.067 (12)*
H4B−0.301400.534200.707500.054 (10)*
H4C−0.296300.541800.856100.045 (10)*
H5−0.177300.403600.701500.0520*
H60.043500.309100.787800.0530*
H70.538200.342500.972800.0520*
H90.416500.403900.689100.0540*
H11A0.229500.350400.393600.0970*
H11B0.271800.253900.380900.0970*
H11C0.411500.323400.415900.0970*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0562 (5)0.0374 (4)0.0361 (4)−0.0009 (4)0.0098 (4)0.0115 (4)
O10.0727 (19)0.0673 (17)0.0342 (14)0.0047 (14)0.0045 (13)0.0126 (12)
O20.0734 (19)0.0353 (13)0.0663 (18)−0.0031 (12)0.0223 (16)0.0181 (12)
O30.0714 (19)0.0473 (15)0.0525 (16)−0.0147 (13)0.0248 (15)−0.0153 (12)
N40.0492 (17)0.0319 (15)0.0492 (18)−0.0021 (13)0.0236 (15)−0.0003 (13)
N70.0384 (15)0.0434 (15)0.0400 (16)−0.0101 (12)0.0036 (12)0.0025 (13)
N80.070 (2)0.0338 (15)0.054 (2)−0.0064 (14)0.0228 (17)−0.0027 (13)
C10.0472 (19)0.0312 (16)0.0365 (17)−0.0034 (14)0.0150 (15)0.0033 (14)
C20.054 (2)0.047 (2)0.0397 (19)−0.0065 (18)0.0054 (17)−0.0115 (17)
C30.061 (3)0.0392 (19)0.052 (2)−0.0047 (19)0.018 (2)−0.0172 (18)
C40.0479 (19)0.0289 (16)0.0368 (17)−0.0075 (14)0.0185 (15)−0.0002 (13)
C50.051 (2)0.0370 (18)0.0382 (18)−0.0006 (16)0.0101 (16)−0.0074 (15)
C60.058 (2)0.0350 (18)0.0340 (19)0.0021 (17)0.0098 (17)−0.0061 (15)
C80.0299 (16)0.0297 (16)0.0416 (18)−0.0035 (14)0.0082 (14)−0.0004 (14)
C90.052 (2)0.0323 (18)0.051 (2)−0.0081 (15)0.0187 (18)0.0008 (16)
C100.042 (2)0.044 (2)0.056 (2)−0.0075 (17)0.023 (2)−0.0054 (17)
C110.072 (3)0.076 (3)0.049 (2)−0.018 (2)0.026 (2)−0.006 (2)
Cl10.0622 (5)0.0392 (5)0.0495 (5)−0.0109 (4)0.0257 (4)−0.0048 (4)
Geometric parameters (Å, º) top
S1—O11.429 (2)C2—C31.372 (6)
S1—O21.433 (2)C3—C41.377 (5)
S1—N71.631 (3)C4—C51.377 (4)
S1—C11.775 (3)C5—C61.387 (5)
O3—N81.415 (4)C8—C91.406 (5)
O3—C101.353 (4)C9—C101.337 (5)
N4—C41.475 (4)C10—C111.470 (6)
N7—C81.393 (4)C2—H20.9301
N8—C81.312 (4)C3—H30.9298
N4—H4B0.9824C5—H50.9297
N4—H4C0.8629C6—H60.9299
N4—H4A0.9222C9—H90.9302
N7—H70.8597C11—H11A0.9599
C1—C21.389 (5)C11—H11B0.9602
C1—C61.377 (4)C11—H11C0.9604
Cl1···N4i3.093 (3)C5···Cl1ix3.616 (3)
Cl1···N73.094 (3)C6···C11xi3.569 (6)
Cl1···C5ii3.616 (3)C6···C83.450 (5)
Cl1···C11iii3.597 (5)C6···O1vi3.389 (4)
Cl1···N4ii3.177 (3)C8···C63.450 (5)
Cl1···H4Ci2.2412C11···O1xii3.316 (5)
Cl1···H72.5476C11···C6xiii3.569 (6)
Cl1···H11Ciii2.9783C11···Cl1xiv3.597 (5)
Cl1···H9iii3.1389C6···H11Bxi3.0598
Cl1···H5ii2.8644C8···H63.0548
Cl1···H4Bii2.1977H2···O12.5475
S1···H6iv3.1907H3···H4A2.5842
O1···C11v3.316 (5)H4A···O2x2.8655
O1···C6iv3.389 (4)H4A···O3x2.6828
O2···N82.926 (4)H4A···N8x1.9296
O3···N7vi3.204 (4)H4A···H32.5842
O1···H11Cv2.7099H4B···H52.3176
O1···H22.5475H4B···Cl1ix2.1977
O1···H6iv2.5292H4C···Cl1viii2.2412
O2···H5iv2.7126H5···Cl1ix2.8644
O2···H4Avii2.8655H5···H4B2.3176
O2···H62.7771H5···O2vi2.7126
O3···H4Avii2.6828H6···O22.7771
O3···H7vi2.5585H6···C83.0548
N4···Cl1viii3.093 (3)H6···S1vi3.1907
N4···Cl1ix3.177 (3)H6···O1vi2.5292
N4···N8x2.843 (4)H7···O3iv2.5586
N7···O3iv3.204 (4)H7···Cl12.5476
N7···Cl13.094 (3)H9···Cl1xiv3.1389
N8···N4vii2.843 (4)H11B···C6xiii3.0598
N8···O22.926 (4)H11C···O1xii2.7099
N8···H4Avii1.9296H11C···Cl1xiv2.9783
O1—S1—O2120.92 (17)C4—C5—C6119.1 (3)
O1—S1—N7104.98 (16)C1—C6—C5119.8 (3)
O1—S1—C1108.03 (15)N7—C8—C9126.6 (3)
O2—S1—N7107.48 (15)N8—C8—C9112.0 (3)
O2—S1—C1108.47 (16)N7—C8—N8121.3 (3)
N7—S1—C1106.01 (15)C8—C9—C10105.4 (3)
N8—O3—C10109.0 (3)O3—C10—C11116.1 (3)
S1—N7—C8124.0 (2)C9—C10—C11134.8 (3)
O3—N8—C8104.4 (2)O3—C10—C9109.1 (3)
H4B—N4—H4C112.95C1—C2—H2120.04
C4—N4—H4C107.71C3—C2—H2119.96
C4—N4—H4A108.80C2—C3—H3120.35
C4—N4—H4B110.81C4—C3—H3120.27
H4A—N4—H4B101.82C4—C5—H5120.39
H4A—N4—H4C114.65C6—C5—H5120.49
S1—N7—H7118.05C1—C6—H6120.09
C8—N7—H7117.99C5—C6—H6120.07
S1—C1—C2120.3 (3)C8—C9—H9127.31
S1—C1—C6119.4 (2)C10—C9—H9127.24
C2—C1—C6120.3 (3)C10—C11—H11A109.50
C1—C2—C3120.0 (4)C10—C11—H11B109.43
C2—C3—C4119.4 (3)C10—C11—H11C109.46
N4—C4—C3119.6 (3)H11A—C11—H11B109.48
N4—C4—C5119.0 (3)H11A—C11—H11C109.49
C3—C4—C5121.4 (3)H11B—C11—H11C109.46
O1—S1—N7—C8174.6 (3)O3—N8—C8—C9−1.6 (4)
O2—S1—N7—C844.7 (3)S1—C1—C6—C5−179.1 (3)
C1—S1—N7—C8−71.2 (3)S1—C1—C2—C3178.0 (3)
O1—S1—C1—C26.7 (3)C6—C1—C2—C3−0.6 (6)
O1—S1—C1—C6−174.7 (3)C2—C1—C6—C5−0.5 (5)
O2—S1—C1—C2139.4 (3)C1—C2—C3—C41.3 (6)
O2—S1—C1—C6−42.0 (3)C2—C3—C4—N4177.9 (3)
N7—S1—C1—C2−105.4 (3)C2—C3—C4—C5−0.9 (6)
N7—S1—C1—C673.2 (3)C3—C4—C5—C6−0.2 (5)
N8—O3—C10—C11−179.3 (3)N4—C4—C5—C6−179.0 (3)
C10—O3—N8—C80.9 (4)C4—C5—C6—C10.9 (5)
N8—O3—C10—C90.1 (4)N8—C8—C9—C101.8 (5)
S1—N7—C8—N8−57.2 (4)N7—C8—C9—C10178.6 (4)
S1—N7—C8—C9126.2 (3)C8—C9—C10—O3−1.1 (4)
O3—N8—C8—N7−178.7 (3)C8—C9—C10—C11178.3 (4)
Symmetry codes: (i) x+1, y, z; (ii) x+1, −y+1, z+1/2; (iii) x, −y+1, z+1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) x, y, z+1; (vi) x−1/2, −y+1/2, z−1/2; (vii) x+1/2, y−1/2, z; (viii) x−1, y, z; (ix) x−1, −y+1, z−1/2; (x) x−1/2, y+1/2, z; (xi) x−1/2, −y+1/2, z+1/2; (xii) x, y, z−1; (xiii) x+1/2, −y+1/2, z−1/2; (xiv) x, −y+1, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N8x0.921.932.843 (4)170
N4—H4B···Cl1ix0.982.203.177 (3)175
N4—H4C···Cl1viii0.862.243.093 (3)169
N7—H7···Cl10.862.553.094 (3)122
N7—H7···O3iv0.862.563.204 (4)133
C2—H2···O10.932.552.926 (5)105
C6—H6···O1vi0.932.533.389 (4)154
Symmetry codes: (iv) x+1/2, −y+1/2, z+1/2; (vi) x−1/2, −y+1/2, z−1/2; (viii) x−1, y, z; (ix) x−1, −y+1, z−1/2; (x) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC10H12N3O3S+·Cl−
Mr289.75
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)8.677 (2), 15.615 (3), 10.435 (2)
β (°) 111.29 (2)
V (Å3)1317.4 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.15 × 0.14 × 0.13
Data collection
DiffractometerPhilips PW 1100
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		2021, 2021, 1318
Rint0.000
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.071, 0.90
No. of reflections2021
No. of parameters167
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.21
Absolute structureFlack (1983), 89 Friedel pairs
Absolute structure parameter−0.05 (7)

Computer programs: FEBO (Belletti, 1996), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
S1—O11.429 (2)O3—C101.353 (4)
S1—O21.433 (2)N4—C41.475 (4)
S1—N71.631 (3)N7—C81.393 (4)
S1—C11.775 (3)N8—C81.312 (4)
O3—N81.415 (4)
O1—S1—O2120.92 (17)S1—C1—C2120.3 (3)
O1—S1—N7104.98 (16)S1—C1—C6119.4 (2)
O1—S1—C1108.03 (15)N4—C4—C3119.6 (3)
O2—S1—N7107.48 (15)N4—C4—C5119.0 (3)
O2—S1—C1108.47 (16)N7—C8—C9126.6 (3)
N7—S1—C1106.01 (15)N8—C8—C9112.0 (3)
N8—O3—C10109.0 (3)N7—C8—N8121.3 (3)
S1—N7—C8124.0 (2)O3—C10—C11116.1 (3)
O3—N8—C8104.4 (2)O3—C10—C9109.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N8i0.921.932.843 (4)170
N4—H4B···Cl1ii0.982.203.177 (3)175
N4—H4C···Cl1iii0.862.243.093 (3)169
N7—H7···Cl10.862.553.094 (3)122
N7—H7···O3iv0.862.563.204 (4)133
C2—H2···O10.932.552.926 (5)105
C6—H6···O1v0.932.533.389 (4)154
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x−1, −y+1, z−1/2; (iii) x−1, y, z; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z−1/2.
 

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