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In the title sulfobetaine (NDSB-195), C7H17NO3S, the three-methyl­ene spacer between the ammonium and sulfonate groups is in a fully extended conformation. Inter­actions between the charged ammonium and sulfonate groups are the most important for the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048069/gk2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048069/gk2041Isup2.hkl
Contains datablock I

CCDC reference: 629686

Key indicators

  • Single-crystal X-ray study
  • T = 106 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.034
  • wR factor = 0.092
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: HKL-3000SM (Minor et al., 2006) and SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: HKL-3000SM and SHELXL97 (Sheldrick, 1997); molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: HKL-3000SM.

ethyldimethylammoniopropane sulfonate top
Crystal data top
C7H17NO3SF(000) = 848
Mr = 195.28Dx = 1.365 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54179 Å
Hall symbol: -P 2ac 2abCell parameters from 1839 reflections
a = 12.369 (1) Åθ = 6.2–72.3°
b = 11.964 (1) ŵ = 2.82 mm1
c = 12.844 (1) ÅT = 106 K
V = 1900.7 (3) Å3Block, colorless
Z = 80.23 × 0.16 × 0.08 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1839 independent reflections
Radiation source: fine-focus sealed tube1695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 10 pixels mm-1θmax = 72.3°, θmin = 6.2°
ω scan with χ offseth = 1515
Absorption correction: multi-scan
(Otwinowski et al., 2003)
k = 1413
Tmin = 0.61, Tmax = 0.80l = 1515
3381 measured reflections
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0463P)2 + 1.4076P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1839 reflectionsΔρmax = 0.29 e Å3
110 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00085 (14)
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
S10.08225 (3)0.00207 (3)0.27742 (3)0.02018 (16)
O20.04113 (9)0.10449 (9)0.32375 (9)0.0269 (3)
O10.16302 (9)0.05369 (10)0.34126 (9)0.0298 (3)
O30.11746 (11)0.01688 (10)0.16996 (9)0.0315 (3)
C60.31850 (13)0.31409 (14)0.42197 (12)0.0253 (4)
H6A0.36860.27350.37910.038*
H6B0.28840.37490.38280.038*
H6C0.35550.34290.48190.038*
C10.02895 (13)0.09220 (14)0.27026 (11)0.0225 (4)
H1A0.00420.16230.24070.027*
H1B0.08310.06140.22380.027*
N10.22956 (10)0.23744 (11)0.45639 (10)0.0193 (3)
C30.17376 (12)0.19619 (13)0.35859 (11)0.0209 (3)
H3A0.14650.26050.32080.025*
H3B0.22720.16000.31480.025*
C20.08100 (12)0.11531 (13)0.37575 (12)0.0213 (3)
H2A0.10760.04630.40600.026*
H2B0.02840.14760.42300.026*
C70.15231 (13)0.30257 (14)0.52325 (12)0.0239 (3)
H7A0.09480.25450.54590.036*
H7B0.19000.33140.58290.036*
H7C0.12280.36350.48380.036*
C40.27470 (14)0.13824 (14)0.51561 (12)0.0258 (4)
H4A0.31980.09500.46880.031*
H4B0.21500.09090.53690.031*
C50.34045 (14)0.16784 (15)0.61085 (13)0.0307 (4)
H5A0.36580.10060.64350.046*
H5B0.40120.21290.59060.046*
H5C0.29620.20890.65890.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0231 (2)0.0171 (3)0.0203 (2)0.00097 (13)0.00163 (13)0.00102 (13)
O20.0272 (6)0.0207 (6)0.0329 (6)0.0003 (5)0.0030 (5)0.0047 (5)
O10.0252 (6)0.0256 (7)0.0387 (7)0.0001 (5)0.0049 (5)0.0071 (5)
O30.0410 (7)0.0293 (7)0.0244 (6)0.0075 (5)0.0098 (5)0.0015 (5)
C60.0235 (8)0.0272 (9)0.0251 (8)0.0075 (7)0.0002 (6)0.0028 (7)
C10.0269 (8)0.0198 (9)0.0209 (8)0.0021 (6)0.0001 (6)0.0006 (6)
N10.0216 (6)0.0167 (7)0.0196 (6)0.0006 (5)0.0007 (5)0.0005 (5)
C30.0248 (7)0.0203 (8)0.0176 (7)0.0022 (6)0.0000 (6)0.0004 (6)
C20.0241 (8)0.0191 (8)0.0207 (7)0.0014 (6)0.0003 (6)0.0000 (6)
C70.0251 (8)0.0224 (8)0.0243 (8)0.0021 (6)0.0020 (6)0.0051 (6)
C40.0329 (9)0.0184 (9)0.0260 (8)0.0032 (6)0.0037 (7)0.0016 (6)
C50.0348 (9)0.0259 (10)0.0315 (9)0.0004 (7)0.0091 (7)0.0041 (7)
Geometric parameters (Å, º) top
S1—O21.4541 (12)C3—C21.517 (2)
S1—O11.4546 (12)C3—H3A0.9700
S1—O31.4581 (12)C3—H3B0.9700
S1—C11.7811 (16)C2—H2A0.9700
C6—N11.4988 (19)C2—H2B0.9700
C6—H6A0.9600C7—H7A0.9600
C6—H6B0.9600C7—H7B0.9600
C6—H6C0.9600C7—H7C0.9600
C1—C21.525 (2)C4—C51.511 (2)
C1—H1A0.9700C4—H4A0.9700
C1—H1B0.9700C4—H4B0.9700
N1—C71.5025 (19)C5—H5A0.9600
N1—C31.5159 (19)C5—H5B0.9600
N1—C41.516 (2)C5—H5C0.9600
O2—S1—O1113.33 (7)N1—C3—H3B108.4
O2—S1—O3112.92 (7)C2—C3—H3B108.4
O1—S1—O3112.60 (8)H3A—C3—H3B107.4
O2—S1—C1106.54 (7)C3—C2—C1107.80 (12)
O1—S1—C1105.61 (7)C3—C2—H2A110.1
O3—S1—C1105.00 (7)C1—C2—H2A110.1
N1—C6—H6A109.5C3—C2—H2B110.1
N1—C6—H6B109.5C1—C2—H2B110.1
H6A—C6—H6B109.5H2A—C2—H2B108.5
N1—C6—H6C109.5N1—C7—H7A109.5
H6A—C6—H6C109.5N1—C7—H7B109.5
H6B—C6—H6C109.5H7A—C7—H7B109.5
C2—C1—S1113.26 (11)N1—C7—H7C109.5
C2—C1—H1A108.9H7A—C7—H7C109.5
S1—C1—H1A108.9H7B—C7—H7C109.5
C2—C1—H1B108.9C5—C4—N1114.89 (13)
S1—C1—H1B108.9C5—C4—H4A108.5
H1A—C1—H1B107.7N1—C4—H4A108.5
C6—N1—C7108.55 (12)C5—C4—H4B108.5
C6—N1—C3106.79 (11)N1—C4—H4B108.5
C7—N1—C3110.66 (11)H4A—C4—H4B107.5
C6—N1—C4110.89 (12)C4—C5—H5A109.5
C7—N1—C4110.70 (12)C4—C5—H5B109.5
C3—N1—C4109.18 (12)H5A—C5—H5B109.5
N1—C3—C2115.57 (12)C4—C5—H5C109.5
N1—C3—H3A108.4H5A—C5—H5C109.5
C2—C3—H3A108.4H5B—C5—H5C109.5
O2—S1—C1—C257.69 (13)N1—C3—C2—C1174.78 (13)
O1—S1—C1—C263.11 (13)S1—C1—C2—C3179.97 (11)
O3—S1—C1—C2177.69 (12)C6—N1—C4—C557.95 (17)
C6—N1—C3—C2179.22 (13)C7—N1—C4—C562.59 (18)
C7—N1—C3—C262.82 (17)C3—N1—C4—C5175.35 (13)
C4—N1—C3—C259.26 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O3i0.972.363.302 (2)164
C4—H4B···O1ii0.972.423.250 (2)143
C7—H7C···O3iii0.962.443.318 (2)152
C7—H7B···O1iv0.962.483.347 (2)150
Symmetry codes: (i) x1/2, y, z+1/2; (ii) x, y, z+1; (iii) x, y+1/2, z+1/2; (iv) x1/2, y+1/2, z+1.
 

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