Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300895X/tk6103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680300895X/tk6103Isup2.hkl |
CCDC reference: 214642
Key indicators
- Single-crystal X-ray study
- T = 295 K
- R factor = 0.031
- wR factor = 0.085
- Data-to-parameter ratio = 11.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 820 Count of symmetry unique reflns 820 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
Compound (I) was isolated from the methanol extract of the marine sponge Xestospongia pacifica from Swain Reefs, Queensland. The extract was subjected to repeated gel-permeation chromatography on Sephadex LH-20 in methanol. Crystals of (I) were obtained on slow evaporation of the methanol from the parent fraction; m.p. 520 K (with decomposition). δH (400 MHz, DMSO-d6, p.p.m.): 4.1 (2H, brs, NH2), 3.16 (3H, s, N–CH3), 3.14 (2H, t, J2,1 = 6.4 Hz, H2), 2.77 (2H, t, J1,2 = 6.4 Hz, H1), (ESMS+): 161.8 (MNa+), (ESMS–) 137.8 (M—H).
H atoms were constrained as riding atoms, fixed to their parent C atoms at a C–H distance of 0.95 Å. Uiso(H) values were set to 1.2Ueq for the parent atom.
Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN and PLATON.
C3H9NO3S | F(000) = 296 |
Mr = 139.18 | Dx = 1.557 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 9.061 (3) Å | θ = 12.9–17.3° |
b = 11.931 (3) Å | µ = 0.46 mm−1 |
c = 5.4924 (15) Å | T = 295 K |
V = 593.8 (3) Å3 | Prismatic, colorless |
Z = 4 | 0.40 × 0.40 × 0.15 mm |
Rigaku AFC-7R diffractometer | 793 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.052 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
ω–2θ scans | h = −11→5 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→15 |
Tmin = 0.836, Tmax = 0.934 | l = −3→7 |
1011 measured reflections | 3 standard reflections every 150 reflections |
820 independent reflections | intensity decay: 0.3% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.18P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.085 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.27 e Å−3 |
820 reflections | Δρmin = −0.24 e Å−3 |
74 parameters | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
0 restraints | Extinction coefficient: 0.154 (12) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.09 (13) |
C3H9NO3S | V = 593.8 (3) Å3 |
Mr = 139.18 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.061 (3) Å | µ = 0.46 mm−1 |
b = 11.931 (3) Å | T = 295 K |
c = 5.4924 (15) Å | 0.40 × 0.40 × 0.15 mm |
Rigaku AFC-7R diffractometer | 793 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.052 |
Tmin = 0.836, Tmax = 0.934 | 3 standard reflections every 150 reflections |
1011 measured reflections | intensity decay: 0.3% |
820 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.085 | Δρmax = 0.27 e Å−3 |
S = 1.06 | Δρmin = −0.24 e Å−3 |
820 reflections | Absolute structure: Flack (1983) |
74 parameters | Absolute structure parameter: −0.09 (13) |
0 restraints |
Experimental. The scan width was (1.79 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. |
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 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.43693 (6) | 0.14685 (4) | 0.65892 (11) | 0.0246 (2) | |
O1 | 0.4695 (2) | 0.02903 (14) | 0.7028 (3) | 0.0352 (5) | |
O2 | 0.4186 (2) | 0.16966 (15) | 0.3985 (3) | 0.0345 (5) | |
O3 | 0.5385 (2) | 0.22346 (18) | 0.7776 (4) | 0.0434 (6) | |
N1 | −0.0013 (2) | 0.12425 (16) | 0.8055 (4) | 0.0283 (6) | |
C1 | 0.2625 (3) | 0.17323 (19) | 0.7963 (4) | 0.0280 (6) | |
C2 | 0.1429 (2) | 0.10053 (18) | 0.6876 (4) | 0.0254 (6) | |
C3 | −0.1270 (3) | 0.0623 (2) | 0.6983 (5) | 0.0370 (8) | |
H1 | 0.26920 | 0.15830 | 0.96600 | 0.0340* | |
H2 | 0.23730 | 0.24990 | 0.77280 | 0.0340* | |
H3 | 0.16740 | 0.02380 | 0.71070 | 0.0310* | |
H4 | 0.13530 | 0.11560 | 0.51780 | 0.0310* | |
H5 | 0.00520 | 0.10670 | 0.95570 | 0.0340* | |
H6 | −0.01880 | 0.19410 | 0.79380 | 0.0340* | |
H7 | −0.21470 | 0.07870 | 0.78630 | 0.0450* | |
H8 | −0.13910 | 0.08380 | 0.53300 | 0.0450* | |
H9 | −0.10800 | −0.01610 | 0.70630 | 0.0450* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0246 (3) | 0.0251 (3) | 0.0241 (3) | −0.0024 (2) | 0.0023 (2) | −0.0027 (2) |
O1 | 0.0403 (10) | 0.0305 (8) | 0.0347 (10) | 0.0088 (7) | 0.0035 (8) | 0.0033 (7) |
O2 | 0.0455 (11) | 0.0326 (8) | 0.0253 (8) | −0.0011 (8) | 0.0048 (8) | 0.0053 (7) |
O3 | 0.0315 (9) | 0.0519 (11) | 0.0469 (11) | −0.0144 (9) | 0.0029 (9) | −0.0189 (10) |
N1 | 0.0245 (9) | 0.0322 (10) | 0.0283 (11) | 0.0004 (8) | 0.0018 (9) | −0.0025 (9) |
C1 | 0.0254 (10) | 0.0283 (10) | 0.0302 (11) | 0.0007 (9) | 0.0052 (9) | −0.0081 (9) |
C2 | 0.0242 (9) | 0.0264 (9) | 0.0256 (11) | −0.0001 (8) | 0.0023 (10) | −0.0030 (9) |
C3 | 0.0262 (11) | 0.0404 (13) | 0.0444 (16) | −0.0051 (10) | −0.0047 (12) | 0.0019 (13) |
S1—O1 | 1.4564 (18) | C1—C2 | 1.511 (3) |
S1—O2 | 1.4654 (18) | C1—H1 | 0.9509 |
S1—O3 | 1.452 (2) | C1—H2 | 0.9516 |
S1—C1 | 1.779 (3) | C2—H3 | 0.9505 |
N1—C2 | 1.485 (3) | C2—H4 | 0.9523 |
N1—C3 | 1.480 (3) | C3—H7 | 0.9505 |
N1—H5 | 0.8532 | C3—H8 | 0.9498 |
N1—H6 | 0.8508 | C3—H9 | 0.9521 |
S1···H6i | 3.1535 | C2···O1iii | 3.243 (3) |
O1···C2ii | 3.243 (3) | C2···O1ii | 3.381 (3) |
O1···N1iii | 2.862 (3) | C3···O1iii | 3.260 (3) |
O1···C2iii | 3.381 (3) | C3···O1ii | 3.302 (3) |
O1···C3iii | 3.302 (3) | C3···O2vii | 3.268 (3) |
O1···C3ii | 3.260 (3) | H1···O2ix | 2.7375 |
O2···C3i | 3.268 (3) | H1···H5 | 2.4707 |
O2···N1i | 2.798 (3) | H1···O3viii | 2.8884 |
O3···N1iv | 2.945 (3) | H2···H6 | 2.4169 |
O3···C1iv | 3.334 (3) | H3···O1 | 2.7384 |
O1···H3 | 2.7384 | H3···H9 | 2.5405 |
O1···H8ii | 2.7318 | H3···O2ii | 2.6455 |
O1···H4ii | 2.6216 | H4···O2 | 2.7267 |
O1···H5iii | 2.1253 | H4···H8 | 2.5165 |
O2···H1v | 2.7375 | H4···O1iii | 2.6216 |
O2···H9iii | 2.7233 | H4···O3vii | 2.6625 |
O2···H6i | 2.0198 | H5···H1 | 2.4707 |
O2···H4 | 2.7267 | H5···O1ii | 2.1253 |
O2···H3iii | 2.6455 | H5···O3viii | 2.5185 |
O3···H7vi | 2.8260 | H6···H2 | 2.4169 |
O3···H1iv | 2.8884 | H6···S1vii | 3.1535 |
O3···H4i | 2.6625 | H6···O2vii | 2.0198 |
O3···H5iv | 2.5185 | H6···O3viii | 2.6036 |
O3···H6iv | 2.6036 | H7···O3x | 2.8260 |
N1···O1ii | 2.862 (3) | H8···H4 | 2.5165 |
N1···O2vii | 2.798 (3) | H8···O1iii | 2.7318 |
N1···O3viii | 2.945 (3) | H9···H3 | 2.5405 |
C1···O3viii | 3.334 (3) | H9···O2ii | 2.7233 |
O1—S1—O2 | 111.33 (10) | S1—C1—H2 | 109.00 |
O1—S1—O3 | 113.89 (11) | C2—C1—H1 | 109.00 |
O1—S1—C1 | 106.29 (11) | C2—C1—H2 | 109.03 |
O2—S1—O3 | 113.15 (12) | H1—C1—H2 | 109.17 |
O2—S1—C1 | 106.28 (11) | N1—C2—H3 | 109.31 |
O3—S1—C1 | 105.15 (11) | N1—C2—H4 | 109.11 |
C2—N1—C3 | 114.10 (19) | C1—C2—H3 | 109.43 |
C2—N1—H6 | 108.52 | C1—C2—H4 | 109.29 |
C3—N1—H5 | 108.38 | H3—C2—H4 | 109.24 |
C2—N1—H5 | 108.30 | N1—C3—H7 | 109.77 |
H5—N1—H6 | 109.05 | N1—C3—H8 | 109.53 |
C3—N1—H6 | 108.41 | N1—C3—H9 | 109.46 |
S1—C1—C2 | 111.59 (15) | H7—C3—H8 | 109.51 |
N1—C2—C1 | 110.44 (18) | H7—C3—H9 | 109.27 |
S1—C1—H1 | 109.01 | H8—C3—H9 | 109.29 |
O1—S1—C1—C2 | −59.98 (18) | C3—N1—C2—C1 | 175.97 (19) |
O2—S1—C1—C2 | 58.72 (18) | S1—C1—C2—N1 | 180.00 (15) |
O3—S1—C1—C2 | 178.94 (16) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y, z+1/2; (iii) −x+1/2, −y, z−1/2; (iv) x+1/2, −y+1/2, −z+2; (v) x, y, z−1; (vi) x+1, y, z; (vii) x−1/2, −y+1/2, −z+1; (viii) x−1/2, −y+1/2, −z+2; (ix) x, y, z+1; (x) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5···O1ii | 0.85 | 2.13 | 2.862 (3) | 144 |
N1—H5···O3viii | 0.85 | 2.52 | 2.945 (3) | 112 |
N1—H6···O2vii | 0.85 | 2.02 | 2.798 (3) | 152 |
Symmetry codes: (ii) −x+1/2, −y, z+1/2; (vii) x−1/2, −y+1/2, −z+1; (viii) x−1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C3H9NO3S |
Mr | 139.18 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 9.061 (3), 11.931 (3), 5.4924 (15) |
V (Å3) | 593.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.40 × 0.40 × 0.15 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.836, 0.934 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1011, 820, 793 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.06 |
No. of reflections | 820 |
No. of parameters | 74 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.09 (13) |
Computer programs: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999), MSC/AFC7 Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1997-2001), TEXSAN and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997), TEXSAN and PLATON.
S1—O1 | 1.4564 (18) | S1—C1 | 1.779 (3) |
S1—O2 | 1.4654 (18) | N1—C2 | 1.485 (3) |
S1—O3 | 1.452 (2) | N1—C3 | 1.480 (3) |
O1—S1—O2 | 111.33 (10) | O3—S1—C1 | 105.15 (11) |
O1—S1—O3 | 113.89 (11) | C2—N1—C3 | 114.10 (19) |
O1—S1—C1 | 106.29 (11) | S1—C1—C2 | 111.59 (15) |
O2—S1—O3 | 113.15 (12) | N1—C2—C1 | 110.44 (18) |
O2—S1—C1 | 106.28 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5···O1i | 0.85 | 2.13 | 2.862 (3) | 144 |
N1—H5···O3ii | 0.85 | 2.52 | 2.945 (3) | 112 |
N1—H6···O2iii | 0.85 | 2.02 | 2.798 (3) | 152 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) x−1/2, −y+1/2, −z+2; (iii) x−1/2, −y+1/2, −z+1. |
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Molecules of 2-(methylamino)ethanesulfonic acid, (I), crystallize in the zwitterionic form with the carboxyl proton transferred to the N atom (Fig. 1 and Table 1). The bond lengths and angles of the molecules are in accord with conventional values (Allan et al., 1987) and related structures (Görbitz et al., 2000).
In the crystal structure, the molecules are linked via a number of N–H···O hydrogen bonds to form a three-dimensional network (Table 2).
In a recent study, N-methyltaurine is reported to be a major osmolyte in a specimen of the tubeworm Lamellibrachia sp. (Yin et al., 2000). Osmolytes are small organic molecules that regulate cell volume by countering osmotic pressure exerted by sea water and it seems reasonable to assume that N-methyltaurine performs a similar role in Xestospongia pacifica.