Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003231/qa0204sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003231/qa0204Isup2.hkl |
CCDC reference: 144697
The title compound was prepared by hydrogenolysis of the benzylated diol with H2 on Pd/C at room temperature in EtOH containing a few drops of aqueous HCl. The crude product was purified by ion-exchange chromatography (H+ form, DOWEXR 50WX8–400) and recrystallized from methanol/tert-butyl methyl ether (m.p. 450–452 K, [α]D20 = +30, c = 0.55, MeOH).
Data collection: Syntex P21 Software (Syntex, 1973); cell refinement: Syntex P21 Software; data reduction: XP21 (Pavelčík, 1993); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); software used to prepare material for publication: SHELXL93.
C7H16NO4+·Cl− | F(000) = 228 |
Mr = 213.66 | Dx = 1.478 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.891 (1) Å | Cell parameters from 20 reflections |
b = 7.345 (1) Å | θ = 4.5–10.2° |
c = 9.497 (2) Å | µ = 0.38 mm−1 |
β = 92.46 (3)° | T = 293 K |
V = 480.24 (14) Å3 | Rectangle shape, colourless |
Z = 2 | 0.6 × 0.5 × 0.2 mm |
Syntex P21 diffractometer | 1222 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 30.1°, θmin = 2.2° |
θ–2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.791, Tmax = 0.926 | l = −13→13 |
1663 measured reflections | 2 standard reflections every 100 reflections |
1566 independent reflections | intensity decay: 15% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 0.91 | Calculated w = 1/[σ2(Fo2) + (0.1308P)2 + 0.3128P] where P = (Fo2 + 2Fc2)/3 |
1461 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.84 e Å−3 |
1 restraint | Δρmin = −0.54 e Å−3 |
C7H16NO4+·Cl− | V = 480.24 (14) Å3 |
Mr = 213.66 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.891 (1) Å | µ = 0.38 mm−1 |
b = 7.345 (1) Å | T = 293 K |
c = 9.497 (2) Å | 0.6 × 0.5 × 0.2 mm |
β = 92.46 (3)° |
Syntex P21 diffractometer | 1222 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.048 |
Tmin = 0.791, Tmax = 0.926 | 2 standard reflections every 100 reflections |
1663 measured reflections | intensity decay: 15% |
1566 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.84 e Å−3 |
1461 reflections | Δρmin = −0.54 e Å−3 |
118 parameters |
x | y | z | Uiso*/Ueq | ||
Cl | 0.70957 (12) | 0.2450 (2) | 0.03053 (11) | 0.0380 (3) | |
O1 | 1.2925 (5) | 0.1946 (6) | −0.1045 (4) | 0.0495 (9) | |
H1 | 1.4032 | 0.2029 | −0.0699 | 0.045* | |
O2 | 0.8081 (4) | 0.2420 (6) | −0.5099 (3) | 0.0366 (6) | |
H8 | 0.7042 | 0.2767 | −0.5458 | 0.082* | |
O3 | 0.4797 (4) | 0.0073 (5) | −0.4623 (3) | 0.0347 (7) | |
H10 | 0.4859 | 0.0528 | −0.5408 | 0.055* | |
O4 | 0.5620 (4) | −0.2935 (4) | −0.2885 (3) | 0.0359 (7) | |
H12 | 0.4610 | −0.2955 | −0.2459 | 0.213* | |
N1 | 0.9569 (4) | 0.0187 (5) | −0.1771 (3) | 0.0257 (6) | |
C1 | 1.2699 (5) | 0.3142 (7) | −0.2207 (5) | 0.0361 (9) | |
H2 | 1.3164 | 0.4348 | −0.1948 | 0.050* | |
H3 | 1.3443 | 0.2702 | −0.2982 | 0.050* | |
C2 | 1.0586 (5) | 0.3198 (6) | −0.2633 (4) | 0.0299 (8) | |
H4 | 0.9874 | 0.3681 | −0.1857 | 0.050* | |
H5 | 1.0403 | 0.4028 | −0.3422 | 0.050* | |
C3 | 0.9740 (5) | 0.1356 (5) | −0.3054 (4) | 0.0235 (6) | |
H6 | 1.0615 | 0.0761 | −0.3698 | 0.050* | |
C4 | 0.7750 (5) | 0.1572 (5) | −0.3797 (4) | 0.0250 (7) | |
H7 | 0.6945 | 0.2367 | −0.3234 | 0.050* | |
C5 | 0.6711 (5) | −0.0216 (5) | −0.4039 (4) | 0.0274 (7) | |
H9 | 0.7441 | −0.0961 | −0.4689 | 0.050* | |
C6 | 0.6559 (5) | −0.1233 (5) | −0.2664 (4) | 0.0262 (7) | |
H11 | 0.5826 | −0.0498 | −0.2010 | 0.050* | |
C7 | 0.8587 (5) | −0.1576 (5) | −0.2044 (4) | 0.0293 (8) | |
H13 | 0.9323 | −0.2289 | −0.2695 | 0.050* | |
H14 | 0.8513 | −0.2259 | −0.1173 | 0.050* | |
H15 | 0.8933 | 0.0932 | −0.1214 | 0.050* | |
H16 | 1.0612 | 0.0178 | −0.1387 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0247 (4) | 0.0467 (5) | 0.0429 (5) | −0.0003 (4) | 0.0047 (3) | −0.0084 (5) |
O1 | 0.0287 (13) | 0.064 (2) | 0.055 (2) | −0.0137 (15) | −0.0130 (13) | 0.010 (2) |
O2 | 0.0258 (11) | 0.046 (2) | 0.0378 (14) | −0.0004 (14) | 0.0027 (10) | 0.016 (2) |
O3 | 0.0224 (12) | 0.046 (2) | 0.035 (2) | −0.0052 (12) | −0.0087 (11) | 0.0063 (15) |
O4 | 0.0388 (14) | 0.034 (2) | 0.0353 (13) | −0.0165 (12) | 0.0053 (11) | −0.0045 (12) |
N1 | 0.0183 (12) | 0.0296 (15) | 0.0290 (14) | −0.0031 (11) | −0.0004 (10) | −0.0005 (13) |
C1 | 0.0232 (15) | 0.044 (2) | 0.042 (2) | −0.011 (2) | 0.0018 (15) | −0.003 (2) |
C2 | 0.026 (2) | 0.026 (2) | 0.038 (2) | −0.0026 (14) | 0.0064 (15) | −0.001 (2) |
C3 | 0.0161 (12) | 0.0276 (15) | 0.027 (2) | −0.0023 (12) | 0.0015 (11) | −0.0001 (13) |
C4 | 0.0163 (12) | 0.029 (2) | 0.030 (2) | −0.0005 (12) | 0.0023 (11) | 0.0017 (14) |
C5 | 0.0216 (14) | 0.031 (2) | 0.030 (2) | −0.0009 (14) | 0.0035 (13) | 0.0008 (14) |
C6 | 0.0226 (15) | 0.026 (2) | 0.030 (2) | −0.0057 (13) | 0.0053 (13) | −0.0025 (15) |
C7 | 0.026 (2) | 0.026 (2) | 0.035 (2) | −0.0023 (14) | −0.0004 (14) | 0.0010 (14) |
O1—C1 | 1.414 (6) | C1—C2 | 1.495 (5) |
O2—C4 | 1.412 (4) | C2—C3 | 1.520 (5) |
O3—C5 | 1.425 (4) | C3—C4 | 1.523 (5) |
O4—C6 | 1.419 (5) | C4—C5 | 1.509 (5) |
N1—C7 | 1.479 (5) | C5—C6 | 1.512 (5) |
N1—C3 | 1.500 (5) | C6—C7 | 1.514 (5) |
C7—N1—C3 | 114.2 (3) | C5—C4—C3 | 113.1 (3) |
O1—C1—C2 | 107.6 (3) | O3—C5—C6 | 108.2 (3) |
C1—C2—C3 | 113.8 (3) | O3—C5—C4 | 110.8 (3) |
N1—C3—C2 | 109.8 (3) | C6—C5—C4 | 110.4 (3) |
N1—C3—C4 | 109.6 (3) | O4—C6—C5 | 110.9 (3) |
C2—C3—C4 | 110.9 (3) | O4—C6—C7 | 108.6 (3) |
O2—C4—C5 | 110.1 (3) | C5—C6—C7 | 108.8 (3) |
O2—C4—C3 | 106.0 (3) | N1—C7—C6 | 109.3 (3) |
Experimental details
Crystal data | |
Chemical formula | C7H16NO4+·Cl− |
Mr | 213.66 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 6.891 (1), 7.345 (1), 9.497 (2) |
β (°) | 92.46 (3) |
V (Å3) | 480.24 (14) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.6 × 0.5 × 0.2 |
Data collection | |
Diffractometer | Syntex P21 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.791, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1663, 1566, 1222 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.157, 0.91 |
No. of reflections | 1461 |
No. of parameters | 118 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.84, −0.54 |
Computer programs: Syntex P21 Software (Syntex, 1973), Syntex P21 Software, XP21 (Pavelčík, 1993), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), SHELXL93.
O1—C1 | 1.414 (6) | C1—C2 | 1.495 (5) |
O2—C4 | 1.412 (4) | C2—C3 | 1.520 (5) |
O3—C5 | 1.425 (4) | C3—C4 | 1.523 (5) |
O4—C6 | 1.419 (5) | C4—C5 | 1.509 (5) |
N1—C7 | 1.479 (5) | C5—C6 | 1.512 (5) |
N1—C3 | 1.500 (5) | C6—C7 | 1.514 (5) |
C7—N1—C3 | 114.2 (3) | C5—C4—C3 | 113.1 (3) |
O1—C1—C2 | 107.6 (3) | O3—C5—C6 | 108.2 (3) |
C1—C2—C3 | 113.8 (3) | O3—C5—C4 | 110.8 (3) |
N1—C3—C2 | 109.8 (3) | C6—C5—C4 | 110.4 (3) |
N1—C3—C4 | 109.6 (3) | O4—C6—C5 | 110.9 (3) |
C2—C3—C4 | 110.9 (3) | O4—C6—C7 | 108.6 (3) |
O2—C4—C5 | 110.1 (3) | C5—C6—C7 | 108.8 (3) |
O2—C4—C3 | 106.0 (3) | N1—C7—C6 | 109.3 (3) |
The title compound [(I); alternative name: 1,5,6-trideoxy-1,5-imino-D-gluco-heptitol hydrochloride] was prepared by palladium(II)-catalyzed aminocarbolation of (2S,3S,4R)-1-benzylamino-2,3-di-O-benzylhex-5-ene-2,3,4-triol with subsequent lactone-ring opening and deprotection (Szolcsányi et al., 1999).
The bond lengths are consistent with average values in the usual sources [International Tables for Crystallography (1992, Vol. C, Table 9.5.1.1)]. The Cl- anion is bonded in the structure by hydrogen bonds [Cl···H15 2.225 Å, Cli···H16 2.725 Å, Clii···H12 2.420 Å and Cliii···H1 2.300 Å; symmetry codes: (i) -x + 2, y - 1/2, -z; (ii) -x + 1, y - 1/2, -z; (iii) x + 1, y, z].