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In the crystal structure of the title compound, C11H10N3O4S+·Cl·0.5H2O, there are two formula units in the asymmetric unit. A network of N—H...Cl, N—H...O and O—H...Cl hydrogen bonds helps to establish the crystal packing. The nitro group of one of the organic cations is disordered over two positions in a 0.57 (2):0.43 (2) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038378/hb2493sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038378/hb2493Isup2.hkl
Contains datablock I

CCDC reference: 660257

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.037
  • wR factor = 0.094
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.10 Deg. O1 -N1 -O1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.90 Deg. O2' -N1 -O2 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 47
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing studies of N-sulfonated derivatives of 4-aminopyridine (Yu & Li, 2007), which contain both an acid and a base centre, we had planned to obtain the neutral zwitterionic crystal structure, but failed. Thus, the crystal structure of the semihydrated HCl title salt, (I), is reported herein.

The asymmetric unit of (I) contains two cations, two anions, and a single water molecule (Fig. 1). The short C—N distances [C7—N2 = 1.385 (2), C18—N5 = 1.382 (3) Å] and planar conformations [S1/H2A/N2/C7 0.0012, S2/H5A/N5/C18 0.0039 Å] indicate that N2 and N5 are sp2 hybridized to a large extent which can be related to tautomeric Lewis structures (Fig. 2). The benzene ring makes angles of 81.07 (12) and 74.80 (11)° with the pyridinium ring in the two asymmetric cations.

The crystal structure of (I) is stabilized by a series of intermolecular N—H···Cl, N—H···O and O—H···Cl hydrogen bonds (Table 1) with the water molecules making important contributions.

Related literature top

For related literature, see: Yu & Li (2007).

Experimental top

2-Nitro-N-(4-pyridyl)benzenesulfonamide was obtained according to the method of Yu & Li (2007). Colourless blocks of (I) were grown by natural evaporation of an aqueous HCl solution of the amide.

Refinement top

The N-bound H atoms were located in a difference map and refined with the constraint N—H = 0.90 (1) Å and their Uiso values were freely refined. The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding atoms and the O-bound H atoms refined as riding in their as-found relative positions. The constraint Uiso(H) = 1.2Ueq(C or O) was applied. O1 and O2 are disordered over two positions and their occupancy ratio 0.57 (2):0.43 (2).

Structure description top

As part of our ongoing studies of N-sulfonated derivatives of 4-aminopyridine (Yu & Li, 2007), which contain both an acid and a base centre, we had planned to obtain the neutral zwitterionic crystal structure, but failed. Thus, the crystal structure of the semihydrated HCl title salt, (I), is reported herein.

The asymmetric unit of (I) contains two cations, two anions, and a single water molecule (Fig. 1). The short C—N distances [C7—N2 = 1.385 (2), C18—N5 = 1.382 (3) Å] and planar conformations [S1/H2A/N2/C7 0.0012, S2/H5A/N5/C18 0.0039 Å] indicate that N2 and N5 are sp2 hybridized to a large extent which can be related to tautomeric Lewis structures (Fig. 2). The benzene ring makes angles of 81.07 (12) and 74.80 (11)° with the pyridinium ring in the two asymmetric cations.

The crystal structure of (I) is stabilized by a series of intermolecular N—H···Cl, N—H···O and O—H···Cl hydrogen bonds (Table 1) with the water molecules making important contributions.

For related literature, see: Yu & Li (2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (I) with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms). Only one of the two disordered components is shown. The water molecule and chloride counterions are omitted for clarity.
[Figure 2] Fig. 2. The tautomerization in the title compound.
4-(2-Nitrobenzenesulfonamido)pyridinium chloride hemihydrate top
Crystal data top
C11H10N3O4S+·Cl·0.5H2OF(000) = 1336
Mr = 324.74Dx = 1.524 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5769 reflections
a = 8.5250 (9) Åθ = 2.3–26.3°
b = 23.686 (3) ŵ = 0.44 mm1
c = 14.0227 (15) ÅT = 294 K
β = 90.533 (2)°Block, colourless
V = 2831.4 (5) Å30.18 × 0.16 × 0.16 mm
Z = 8
Data collection top
Bruker SMART 1000 CCD
diffractometer
5788 independent reflections
Radiation source: fine-focus sealed tube4324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 410
Tmin = 0.925, Tmax = 0.933k = 2929
16156 measured reflectionsl = 1717
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: difmap and geom
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0414P)2 + 0.8236P]
where P = (Fo2 + 2Fc2)/3
5788 reflections(Δ/σ)max = 0.002
405 parametersΔρmax = 0.21 e Å3
47 restraintsΔρmin = 0.42 e Å3
Crystal data top
C11H10N3O4S+·Cl·0.5H2OV = 2831.4 (5) Å3
Mr = 324.74Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.5250 (9) ŵ = 0.44 mm1
b = 23.686 (3) ÅT = 294 K
c = 14.0227 (15) Å0.18 × 0.16 × 0.16 mm
β = 90.533 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
5788 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4324 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.933Rint = 0.032
16156 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03747 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å3
5788 reflectionsΔρmin = 0.42 e Å3
405 parameters
Special details top

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*/UeqOcc. (<1)
S11.03471 (6)0.62128 (2)0.81960 (4)0.03895 (14)
S20.48816 (6)0.39225 (2)0.71431 (4)0.03662 (14)
O11.1118 (19)0.7890 (4)0.6842 (10)0.121 (3)0.57 (2)
O21.0429 (14)0.7078 (3)0.6537 (5)0.076 (2)0.57 (2)
O1'1.1554 (13)0.7854 (5)0.7061 (11)0.081 (3)0.43 (2)
O2'1.117 (2)0.7006 (3)0.6807 (11)0.084 (4)0.43 (2)
O31.19801 (18)0.62714 (8)0.80367 (14)0.0666 (5)
O40.9807 (2)0.58378 (7)0.89101 (11)0.0608 (5)
O50.3534 (3)0.22474 (9)0.78593 (15)0.0826 (6)
O60.4843 (2)0.29184 (8)0.85010 (12)0.0700 (6)
O70.33755 (17)0.38247 (7)0.75352 (12)0.0521 (4)
O80.5093 (2)0.43636 (6)0.64641 (11)0.0495 (4)
N11.0708 (3)0.74400 (11)0.71537 (18)0.0639 (6)
N20.96220 (19)0.60102 (8)0.71765 (12)0.0375 (4)
N30.5063 (2)0.56738 (8)0.63932 (14)0.0424 (4)
N40.4476 (2)0.26339 (8)0.78224 (14)0.0469 (5)
N50.6065 (2)0.40375 (7)0.80458 (12)0.0359 (4)
N61.0631 (2)0.46045 (8)0.81160 (13)0.0410 (4)
C10.9552 (2)0.68867 (9)0.85036 (15)0.0378 (5)
C20.9868 (3)0.74034 (10)0.80580 (17)0.0464 (6)
C30.9357 (3)0.79051 (11)0.8440 (2)0.0681 (8)
H30.95850.82450.81390.082*
C40.8512 (4)0.79018 (14)0.9263 (3)0.0779 (9)
H40.81770.82410.95250.093*
C50.8156 (3)0.74069 (14)0.9704 (2)0.0696 (8)
H50.75610.74101.02560.084*
C60.8679 (3)0.68969 (11)0.93307 (16)0.0512 (6)
H60.84390.65610.96390.061*
C70.8072 (2)0.58892 (8)0.69514 (13)0.0298 (4)
C80.7726 (2)0.57271 (9)0.60155 (14)0.0368 (5)
H80.85230.56910.55710.044*
C90.6209 (3)0.56218 (10)0.57608 (16)0.0433 (5)
H90.59710.55130.51390.052*
C100.5367 (2)0.58106 (9)0.72950 (16)0.0417 (5)
H100.45440.58350.77240.050*
C110.6855 (2)0.59159 (9)0.76047 (14)0.0369 (5)
H110.70560.60040.82410.044*
C120.5541 (2)0.32936 (8)0.65867 (14)0.0337 (4)
C130.5231 (2)0.27450 (9)0.69050 (14)0.0374 (5)
C140.5657 (3)0.22817 (10)0.63775 (17)0.0490 (6)
H140.54160.19200.65900.059*
C150.6440 (3)0.23546 (11)0.55351 (18)0.0565 (7)
H150.67370.20410.51810.068*
C160.6784 (3)0.28830 (12)0.52147 (17)0.0574 (7)
H160.73310.29280.46490.069*
C170.6319 (3)0.33548 (10)0.57315 (15)0.0449 (5)
H170.65330.37140.55000.054*
C180.7598 (2)0.42265 (8)0.80218 (13)0.0315 (4)
C190.8394 (3)0.42707 (9)0.88944 (14)0.0401 (5)
H190.78990.41690.94570.048*
C200.9895 (3)0.44628 (10)0.89160 (16)0.0442 (5)
H201.04180.44960.94980.053*
C210.9919 (3)0.45634 (9)0.72684 (15)0.0413 (5)
H211.04580.46630.67200.050*
C220.8408 (2)0.43766 (9)0.71951 (14)0.0373 (5)
H220.79200.43490.66010.045*
Cl10.17769 (6)0.55281 (3)0.55557 (4)0.04462 (15)
Cl20.47855 (7)0.40063 (2)1.01277 (4)0.04624 (15)
H2A1.033 (2)0.5975 (9)0.6730 (12)0.046 (6)*
H3A0.4067 (15)0.5622 (11)0.6200 (18)0.067 (8)*
H5A0.566 (3)0.3957 (10)0.8619 (10)0.051 (7)*
H6A1.1596 (16)0.4746 (10)0.8193 (16)0.054 (7)*
O90.3370 (2)0.49762 (7)0.88677 (14)0.0659 (5)
H9A0.36470.53060.90520.079*
H9B0.36060.47120.92620.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0333 (3)0.0443 (3)0.0391 (3)0.0065 (2)0.0087 (2)0.0084 (2)
S20.0367 (3)0.0363 (3)0.0368 (3)0.0019 (2)0.0038 (2)0.0046 (2)
O10.151 (7)0.092 (4)0.120 (6)0.017 (4)0.020 (5)0.040 (4)
O20.085 (5)0.082 (3)0.061 (3)0.002 (3)0.022 (3)0.007 (2)
O1'0.059 (4)0.081 (4)0.102 (6)0.036 (3)0.004 (3)0.041 (3)
O2'0.103 (7)0.073 (4)0.075 (5)0.007 (4)0.049 (5)0.002 (3)
O30.0276 (8)0.0855 (13)0.0866 (13)0.0101 (9)0.0136 (8)0.0393 (11)
O40.0938 (14)0.0483 (10)0.0400 (9)0.0097 (10)0.0093 (9)0.0078 (8)
O50.0980 (16)0.0706 (13)0.0795 (14)0.0444 (12)0.0195 (12)0.0031 (11)
O60.0959 (15)0.0742 (13)0.0398 (9)0.0324 (11)0.0064 (9)0.0037 (9)
O70.0333 (8)0.0607 (10)0.0623 (10)0.0006 (8)0.0023 (7)0.0177 (8)
O80.0672 (11)0.0386 (8)0.0426 (9)0.0057 (8)0.0135 (8)0.0036 (7)
N10.0532 (14)0.0618 (15)0.0769 (17)0.0045 (13)0.0097 (12)0.0191 (14)
N20.0243 (9)0.0565 (11)0.0318 (9)0.0019 (8)0.0041 (7)0.0112 (8)
N30.0274 (9)0.0438 (11)0.0559 (12)0.0043 (8)0.0067 (9)0.0009 (9)
N40.0528 (12)0.0417 (11)0.0463 (11)0.0074 (10)0.0006 (9)0.0040 (9)
N50.0367 (10)0.0442 (10)0.0268 (9)0.0064 (8)0.0039 (7)0.0023 (8)
N60.0338 (10)0.0394 (10)0.0498 (11)0.0044 (8)0.0013 (9)0.0022 (8)
C10.0299 (11)0.0431 (12)0.0403 (11)0.0027 (9)0.0032 (9)0.0075 (10)
C20.0359 (12)0.0466 (13)0.0568 (14)0.0003 (10)0.0005 (11)0.0015 (11)
C30.0618 (17)0.0426 (15)0.100 (2)0.0033 (13)0.0060 (17)0.0067 (15)
C40.072 (2)0.062 (2)0.099 (2)0.0185 (17)0.0040 (18)0.0375 (18)
C50.0628 (18)0.085 (2)0.0612 (17)0.0119 (16)0.0072 (14)0.0286 (16)
C60.0494 (14)0.0611 (16)0.0431 (13)0.0021 (12)0.0029 (11)0.0110 (12)
C70.0256 (10)0.0310 (10)0.0327 (10)0.0015 (8)0.0002 (8)0.0005 (8)
C80.0330 (11)0.0477 (12)0.0297 (10)0.0017 (10)0.0022 (8)0.0018 (9)
C90.0418 (12)0.0504 (13)0.0375 (12)0.0028 (11)0.0080 (10)0.0012 (10)
C100.0302 (11)0.0442 (12)0.0510 (13)0.0005 (10)0.0104 (10)0.0021 (10)
C110.0327 (11)0.0458 (12)0.0324 (10)0.0001 (9)0.0054 (9)0.0075 (9)
C120.0323 (10)0.0376 (11)0.0310 (10)0.0003 (9)0.0044 (8)0.0041 (8)
C130.0374 (11)0.0390 (12)0.0358 (11)0.0026 (9)0.0053 (9)0.0015 (9)
C140.0535 (14)0.0382 (12)0.0551 (15)0.0002 (11)0.0077 (12)0.0071 (11)
C150.0609 (16)0.0526 (15)0.0560 (15)0.0090 (13)0.0011 (13)0.0214 (12)
C160.0622 (16)0.0704 (18)0.0397 (13)0.0004 (14)0.0113 (12)0.0127 (12)
C170.0533 (14)0.0478 (13)0.0337 (11)0.0057 (11)0.0024 (10)0.0022 (10)
C180.0379 (11)0.0255 (10)0.0311 (10)0.0006 (8)0.0030 (8)0.0008 (8)
C190.0441 (12)0.0486 (13)0.0278 (10)0.0071 (11)0.0031 (9)0.0021 (9)
C200.0468 (13)0.0482 (13)0.0374 (12)0.0068 (11)0.0066 (10)0.0000 (10)
C210.0430 (12)0.0410 (12)0.0400 (12)0.0004 (10)0.0097 (10)0.0038 (10)
C220.0436 (12)0.0390 (12)0.0294 (10)0.0016 (10)0.0017 (9)0.0014 (9)
Cl10.0289 (3)0.0648 (4)0.0403 (3)0.0078 (2)0.0057 (2)0.0085 (3)
Cl20.0581 (4)0.0463 (3)0.0345 (3)0.0068 (3)0.0103 (2)0.0017 (2)
O90.0635 (11)0.0456 (10)0.0881 (14)0.0060 (9)0.0275 (10)0.0018 (9)
Geometric parameters (Å, º) top
S1—O41.4186 (18)C4—H40.9300
S1—O31.4187 (17)C5—C61.391 (4)
S1—N21.6248 (17)C5—H50.9300
S1—C11.788 (2)C6—H60.9300
S2—O71.4205 (16)C7—C111.392 (3)
S2—O81.4262 (16)C7—C81.396 (3)
S2—N51.6343 (17)C8—C91.362 (3)
S2—C121.775 (2)C8—H80.9300
O1—N11.204 (7)C9—H90.9300
O2—N11.240 (6)C10—C111.360 (3)
O1'—N11.225 (7)C10—H100.9300
O2'—N11.206 (7)C11—H110.9300
O5—N41.219 (2)C12—C171.383 (3)
O6—N41.205 (2)C12—C131.400 (3)
N1—C21.465 (3)C13—C141.374 (3)
N2—C71.385 (2)C14—C151.373 (3)
N2—H2A0.878 (10)C14—H140.9300
N3—C101.328 (3)C15—C161.363 (4)
N3—C91.331 (3)C15—H150.9300
N3—H3A0.897 (10)C16—C171.392 (3)
N4—C131.468 (3)C16—H160.9300
N5—C181.382 (3)C17—H170.9300
N5—H5A0.897 (10)C18—C191.398 (3)
N6—C211.333 (3)C18—C221.401 (3)
N6—C201.333 (3)C19—C201.358 (3)
N6—H6A0.894 (10)C19—H190.9300
C1—C61.384 (3)C20—H200.9300
C1—C21.401 (3)C21—C221.365 (3)
C2—C31.376 (3)C21—H210.9300
C3—C41.366 (4)C22—H220.9300
C3—H30.9300O9—H9A0.8562
C4—C51.361 (4)O9—H9B0.8575
O4—S1—O3119.87 (12)C1—C6—C5120.5 (3)
O4—S1—N2108.22 (10)C1—C6—H6119.8
O3—S1—N2104.84 (10)C5—C6—H6119.8
O4—S1—C1105.20 (10)N2—C7—C11123.75 (18)
O3—S1—C1108.99 (11)N2—C7—C8117.63 (18)
N2—S1—C1109.51 (10)C11—C7—C8118.62 (18)
O7—S2—O8119.89 (11)C9—C8—C7119.3 (2)
O7—S2—N5106.33 (9)C9—C8—H8120.4
O8—S2—N5108.30 (9)C7—C8—H8120.4
O7—S2—C12108.93 (10)N3—C9—C8120.6 (2)
O8—S2—C12106.19 (10)N3—C9—H9119.7
N5—S2—C12106.53 (9)C8—C9—H9119.7
O1—N1—O2'120.7 (8)N3—C10—C11121.4 (2)
O1—N1—O1'23.1 (9)N3—C10—H10119.3
O2'—N1—O1'116.4 (10)C11—C10—H10119.3
O1—N1—O2114.4 (9)C10—C11—C7118.70 (19)
O2'—N1—O235.9 (6)C10—C11—H11120.6
O1'—N1—O2126.1 (8)C7—C11—H11120.6
O1—N1—C2120.9 (7)C17—C12—C13117.85 (19)
O2'—N1—C2117.6 (5)C17—C12—S2116.70 (16)
O1'—N1—C2115.6 (8)C13—C12—S2125.25 (16)
O2—N1—C2118.1 (4)C14—C13—C12121.2 (2)
C7—N2—S1128.01 (14)C14—C13—N4116.7 (2)
C7—N2—H2A118.6 (15)C12—C13—N4122.11 (18)
S1—N2—H2A113.4 (15)C15—C14—C13119.7 (2)
C10—N3—C9121.26 (19)C15—C14—H14120.1
C10—N3—H3A119.8 (17)C13—C14—H14120.1
C9—N3—H3A118.9 (17)C16—C15—C14120.5 (2)
O6—N4—O5123.6 (2)C16—C15—H15119.8
O6—N4—C13118.63 (19)C14—C15—H15119.8
O5—N4—C13117.80 (19)C15—C16—C17120.2 (2)
C18—N5—S2127.75 (14)C15—C16—H16119.9
C18—N5—H5A117.5 (15)C17—C16—H16119.9
S2—N5—H5A114.8 (15)C12—C17—C16120.6 (2)
C21—N6—C20121.20 (19)C12—C17—H17119.7
C21—N6—H6A123.1 (15)C16—C17—H17119.7
C20—N6—H6A115.6 (15)N5—C18—C19117.04 (17)
C6—C1—C2117.7 (2)N5—C18—C22125.15 (18)
C6—C1—S1115.20 (18)C19—C18—C22117.82 (19)
C2—C1—S1126.65 (17)C20—C19—C18119.63 (19)
C3—C2—C1121.2 (2)C20—C19—H19120.2
C3—C2—N1116.4 (2)C18—C19—H19120.2
C1—C2—N1122.4 (2)N6—C20—C19121.1 (2)
C4—C3—C2119.7 (3)N6—C20—H20119.5
C4—C3—H3120.2C19—C20—H20119.5
C2—C3—H3120.2N6—C21—C22120.8 (2)
C5—C4—C3120.7 (3)N6—C21—H21119.6
C5—C4—H4119.7C22—C21—H21119.6
C3—C4—H4119.7C21—C22—C18119.47 (19)
C4—C5—C6120.2 (3)C21—C22—H22120.3
C4—C5—H5119.9C18—C22—H22120.3
C6—C5—H5119.9H9A—O9—H9B114.1
O4—S1—N2—C750.4 (2)C7—C8—C9—N30.2 (3)
O3—S1—N2—C7179.47 (19)C9—N3—C10—C111.6 (3)
C1—S1—N2—C763.7 (2)N3—C10—C11—C71.3 (3)
O7—S2—N5—C18170.52 (18)N2—C7—C11—C10177.3 (2)
O8—S2—N5—C1840.4 (2)C8—C7—C11—C103.2 (3)
C12—S2—N5—C1873.41 (19)O7—S2—C12—C17140.21 (16)
O4—S1—C1—C61.64 (19)O8—S2—C12—C179.81 (19)
O3—S1—C1—C6128.10 (18)N5—S2—C12—C17105.48 (17)
N2—S1—C1—C6117.74 (17)O7—S2—C12—C1334.6 (2)
O4—S1—C1—C2174.05 (19)O8—S2—C12—C13164.97 (17)
O3—S1—C1—C244.3 (2)N5—S2—C12—C1379.74 (19)
N2—S1—C1—C269.9 (2)C17—C12—C13—C141.2 (3)
C6—C1—C2—C31.4 (3)S2—C12—C13—C14173.48 (17)
S1—C1—C2—C3170.88 (19)C17—C12—C13—N4177.22 (19)
C6—C1—C2—N1176.7 (2)S2—C12—C13—N48.1 (3)
S1—C1—C2—N111.1 (3)O6—N4—C13—C14138.6 (2)
O1—N1—C2—C310.3 (10)O5—N4—C13—C1439.6 (3)
O2'—N1—C2—C3179.7 (13)O6—N4—C13—C1239.9 (3)
O1'—N1—C2—C335.9 (7)O5—N4—C13—C12141.8 (2)
O2—N1—C2—C3139.5 (7)C12—C13—C14—C151.8 (3)
O1—N1—C2—C1171.6 (10)N4—C13—C14—C15176.7 (2)
O2'—N1—C2—C12.2 (13)C13—C14—C15—C160.6 (4)
O1'—N1—C2—C1145.9 (7)C14—C15—C16—C171.2 (4)
O2—N1—C2—C138.6 (8)C13—C12—C17—C160.5 (3)
C1—C2—C3—C40.7 (4)S2—C12—C17—C16175.69 (18)
N1—C2—C3—C4177.5 (3)C15—C16—C17—C121.7 (4)
C2—C3—C4—C50.7 (5)S2—N5—C18—C19177.51 (16)
C3—C4—C5—C61.4 (5)S2—N5—C18—C222.6 (3)
C2—C1—C6—C50.7 (3)N5—C18—C19—C20178.9 (2)
S1—C1—C6—C5172.4 (2)C22—C18—C19—C201.0 (3)
C4—C5—C6—C10.6 (4)C21—N6—C20—C190.1 (3)
S1—N2—C7—C111.2 (3)C18—C19—C20—N60.8 (3)
S1—N2—C7—C8179.33 (16)C20—N6—C21—C220.3 (3)
N2—C7—C8—C9178.0 (2)N6—C21—C22—C180.0 (3)
C11—C7—C8—C92.5 (3)N5—C18—C22—C21179.3 (2)
C10—N3—C9—C82.3 (3)C19—C18—C22—C210.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl1i0.88 (1)2.32 (1)3.1500 (17)157 (2)
N3—H3A···Cl10.90 (1)2.16 (1)3.0472 (18)173 (2)
N5—H5A···Cl20.90 (1)2.25 (1)3.1270 (17)164 (2)
N6—H6A···O9i0.89 (1)1.86 (1)2.700 (2)156 (2)
O9—H9A···Cl2ii0.862.393.1979 (18)157
O9—H9B···Cl20.862.293.1332 (19)167
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC11H10N3O4S+·Cl·0.5H2O
Mr324.74
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)8.5250 (9), 23.686 (3), 14.0227 (15)
β (°) 90.533 (2)
V3)2831.4 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.18 × 0.16 × 0.16
Data collection
DiffractometerBruker SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.925, 0.933
No. of measured, independent and
observed [I > 2σ(I)] reflections
16156, 5788, 4324
Rint0.032
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.094, 1.04
No. of reflections5788
No. of parameters405
No. of restraints47
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.42

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl1i0.878 (10)2.321 (13)3.1500 (17)157 (2)
N3—H3A···Cl10.897 (10)2.155 (11)3.0472 (18)173 (2)
N5—H5A···Cl20.897 (10)2.253 (11)3.1270 (17)164 (2)
N6—H6A···O9i0.894 (10)1.858 (13)2.700 (2)156 (2)
O9—H9A···Cl2ii0.862.393.1979 (18)157
O9—H9B···Cl20.862.293.1332 (19)167
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+2.
 

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