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In the crystal structure of the title compound, C10H14NO2S5+·Cl, the seven-membered ring adopts a chair conformation. The crystal structure is stabilized by N—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200507X/ci6099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200507X/ci6099Isup2.hkl
Contains datablock I

CCDC reference: 183817

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.054
  • wR factor = 0.133
  • Data-to-parameter ratio = 21.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Varacinium chloride top
Crystal data top
C10H14NO2S5+·ClF(000) = 776
Mr = 375.97Dx = 1.535 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.891 (3) ÅCell parameters from 1998 reflections
b = 10.6971 (16) Åθ = 1–27.5°
c = 9.1959 (13) ŵ = 0.87 mm1
β = 101.673 (4)°T = 294 K
V = 1627.2 (4) Å3Needle, yellow
Z = 40.28 × 0.10 × 0.08 mm
Data collection top
Bruker CCD area-detector
diffractometer
3720 independent reflections
Radiation source: fine-focus sealed tube1234 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
φ and ω scansθmax = 27.6°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1621
Tmin = 0.778, Tmax = 0.928k = 1313
10836 measured reflectionsl = 1111
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133Riding
S = 0.81 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
3726 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.27 e Å3
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*/Ueq
Cl10.55850 (8)0.38522 (10)0.20629 (14)0.0622 (4)
S10.30842 (8)0.48023 (12)0.19846 (15)0.0672 (4)
S20.36804 (9)0.56438 (12)0.38780 (18)0.0755 (5)
S30.29511 (10)0.71263 (13)0.41331 (19)0.0888 (6)
S40.19983 (10)0.62576 (14)0.4793 (2)0.0986 (6)
S50.13415 (9)0.54532 (14)0.2917 (2)0.0917 (6)
O10.0458 (2)0.3212 (4)0.3376 (5)0.0961 (13)
O20.0989 (2)0.0839 (3)0.3664 (5)0.0944 (13)
C10.2493 (3)0.3626 (4)0.2621 (5)0.0535 (13)
C20.1735 (3)0.3914 (4)0.2957 (6)0.0619 (14)
C30.1253 (3)0.2944 (6)0.3267 (6)0.0735 (16)
C40.1521 (3)0.1705 (5)0.3343 (6)0.0687 (15)
C50.2270 (3)0.1453 (4)0.3051 (5)0.0611 (14)
H50.24550.06320.31040.073*
C60.2756 (3)0.2391 (4)0.2680 (5)0.0493 (12)
C70.3578 (3)0.2005 (4)0.2414 (5)0.0502 (12)
H7A0.35430.11770.19740.060*
H7B0.37490.25830.17250.060*
C80.4186 (3)0.1997 (4)0.3843 (5)0.0475 (12)
H8A0.42320.28340.42600.057*
H8B0.39990.14490.45430.057*
C90.0286 (4)0.3095 (6)0.4758 (7)0.117 (3)
H9A0.02350.34540.47600.176*
H9B0.06900.35230.54670.176*
H9C0.02820.22260.50170.176*
C100.1209 (4)0.0435 (5)0.3654 (7)0.098 (2)
H10A0.07810.09430.38780.147*
H10B0.16930.05740.43870.147*
H10C0.13030.06530.26910.147*
N10.4995 (2)0.1573 (3)0.3649 (4)0.0509 (10)
H1A0.53370.15820.45230.076*
H1B0.51750.20840.30230.076*
H1C0.49580.08000.32840.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0763 (9)0.0410 (6)0.0662 (9)0.0047 (7)0.0072 (7)0.0061 (6)
S10.0660 (10)0.0628 (8)0.0798 (10)0.0079 (8)0.0314 (8)0.0130 (8)
S20.0637 (10)0.0594 (8)0.1044 (12)0.0014 (8)0.0199 (9)0.0018 (8)
S30.0888 (12)0.0535 (8)0.1343 (14)0.0027 (8)0.0464 (11)0.0025 (9)
S40.1095 (14)0.0759 (10)0.1295 (15)0.0082 (10)0.0695 (13)0.0023 (10)
S50.0610 (10)0.0747 (10)0.1467 (16)0.0238 (9)0.0381 (11)0.0233 (10)
O10.065 (3)0.109 (3)0.115 (4)0.009 (2)0.021 (3)0.020 (3)
O20.064 (3)0.068 (3)0.154 (4)0.017 (2)0.029 (3)0.009 (3)
C10.047 (3)0.058 (3)0.059 (3)0.005 (3)0.021 (3)0.009 (3)
C20.042 (3)0.055 (3)0.091 (4)0.003 (3)0.019 (3)0.011 (3)
C30.042 (4)0.087 (4)0.094 (4)0.006 (3)0.019 (3)0.004 (4)
C40.050 (4)0.063 (4)0.092 (4)0.006 (3)0.013 (3)0.006 (3)
C50.057 (4)0.051 (3)0.074 (4)0.007 (3)0.010 (3)0.003 (3)
C60.045 (3)0.048 (3)0.056 (3)0.004 (3)0.012 (3)0.003 (2)
C70.057 (3)0.046 (3)0.049 (3)0.010 (3)0.014 (3)0.002 (2)
C80.052 (3)0.048 (3)0.048 (3)0.009 (2)0.022 (3)0.001 (2)
C90.144 (7)0.135 (6)0.087 (5)0.036 (5)0.058 (5)0.012 (4)
C100.094 (5)0.065 (4)0.136 (6)0.035 (4)0.025 (4)0.001 (4)
N10.052 (3)0.046 (2)0.057 (3)0.002 (2)0.017 (2)0.0053 (19)
Geometric parameters (Å, º) top
S1—C11.777 (4)C6—C71.515 (5)
S1—S22.036 (2)C7—C81.495 (6)
S2—S32.051 (2)C7—H7A0.97
S3—S42.054 (2)C7—H7B0.97
S4—S52.043 (3)C8—N11.484 (5)
S5—C21.773 (5)C8—H8A0.97
O1—C91.366 (6)C8—H8B0.97
O1—C31.396 (6)C9—H9A0.96
O2—C41.363 (5)C9—H9B0.96
O2—C101.413 (5)C9—H9C0.96
C1—C61.391 (6)C10—H10A0.96
C1—C21.411 (6)C10—H10B0.96
C2—C31.385 (6)C10—H10C0.96
C3—C41.398 (6)N1—H1A0.89
C4—C51.373 (6)N1—H1B0.89
C5—C61.382 (6)N1—H1C0.89
C5—H50.93
C1—S1—S2104.17 (17)C8—C7—H7B109.6
S1—S2—S3103.59 (9)C6—C7—H7B109.6
S2—S3—S4102.05 (8)H7A—C7—H7B108.1
S5—S4—S3105.36 (9)N1—C8—C7112.4 (3)
C2—S5—S4103.66 (19)N1—C8—H8A109.1
C9—O1—C3115.9 (5)C7—C8—H8A109.1
C4—O2—C10117.9 (4)N1—C8—H8B109.1
C6—C1—C2119.7 (4)C7—C8—H8B109.1
C6—C1—S1119.3 (4)H8A—C8—H8B107.9
C2—C1—S1120.8 (4)O1—C9—H9A109.5
C3—C2—C1118.6 (4)O1—C9—H9B109.5
C3—C2—S5117.8 (4)H9A—C9—H9B109.5
C1—C2—S5123.5 (4)O1—C9—H9C109.5
C2—C3—O1118.4 (5)H9A—C9—H9C109.5
C2—C3—C4121.5 (5)H9B—C9—H9C109.5
O1—C3—C4119.9 (5)O2—C10—H10A109.5
O2—C4—C5125.7 (5)O2—C10—H10B109.5
O2—C4—C3115.7 (5)H10A—C10—H10B109.5
C5—C4—C3118.6 (5)O2—C10—H10C109.5
C4—C5—C6121.6 (5)H10A—C10—H10C109.5
C4—C5—H5119.2H10B—C10—H10C109.5
C6—C5—H5119.2C8—N1—H1A109.5
C5—C6—C1119.8 (4)C8—N1—H1B109.5
C5—C6—C7116.9 (4)H1A—N1—H1B109.5
C1—C6—C7123.2 (4)C8—N1—H1C109.5
C8—C7—C6110.4 (3)H1A—N1—H1C109.5
C8—C7—H7A109.6H1B—N1—H1C109.5
C6—C7—H7A109.6
C1—S1—S2—S393.78 (17)C10—O2—C4—C52.1 (8)
S1—S2—S3—S473.00 (11)C10—O2—C4—C3175.8 (5)
S2—S3—S4—S575.16 (11)C2—C3—C4—O2179.7 (5)
S3—S4—S5—C293.11 (19)O1—C3—C4—O26.0 (8)
S2—S1—C1—C6101.5 (4)C2—C3—C4—C52.2 (9)
S2—S1—C1—C283.4 (4)O1—C3—C4—C5172.0 (5)
C6—C1—C2—C33.1 (7)O2—C4—C5—C6177.5 (5)
S1—C1—C2—C3172.0 (4)C3—C4—C5—C60.3 (8)
C6—C1—C2—S5180.0 (4)C4—C5—C6—C11.1 (7)
S1—C1—C2—S54.9 (6)C4—C5—C6—C7178.7 (4)
S4—S5—C2—C3108.5 (4)C2—C1—C6—C50.7 (7)
S4—S5—C2—C174.6 (4)S1—C1—C6—C5174.5 (3)
C1—C2—C3—O1170.4 (4)C2—C1—C6—C7176.8 (4)
S5—C2—C3—O16.6 (7)S1—C1—C6—C78.0 (6)
C1—C2—C3—C43.9 (8)C5—C6—C7—C887.2 (5)
S5—C2—C3—C4179.0 (4)C1—C6—C7—C890.4 (5)
C9—O1—C3—C2112.1 (6)C6—C7—C8—N1177.6 (3)
C9—O1—C3—C473.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···Cl10.892.263.107 (3)160
N1—H1A···Cl1i0.892.333.129 (4)149
N1—H1C···Cl1ii0.892.273.098 (3)154
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.
 

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