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In the crystal structure of the title compound, C10H21NO5, mol­ecules are linked by strong N—H...O and O—H...N hydrogen bonds into infinite zigzag chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045430/wn2082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045430/wn2082Isup2.hkl
Contains datablock I

CCDC reference: 630503

Key indicators

  • Single-crystal X-ray study
  • T = 88 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.065
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 1471 Count of symmetry unique reflns 1476 Completeness (_total/calc) 99.66% 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 no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1L-1-Amino-1-deoxy-2,3,4,5-tetra-O-methyl-scyllo-inositol top
Crystal data top
C10H21NO5F(000) = 512
Mr = 235.28Dx = 1.276 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1993 reflections
a = 6.7256 (14) Åθ = 2.9–21.0°
b = 12.920 (3) ŵ = 0.10 mm1
c = 14.091 (3) ÅT = 88 K
V = 1224.4 (5) Å3Needle, colourless
Z = 40.50 × 0.10 × 0.05 mm
Data collection top
Bruker–Nonius APEX2 CCD area-detector
diffractometer
1471 independent reflections
Radiation source: fine-focus sealed tube913 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.1°
φ and ω scansh = 88
Absorption correction: multi-scan
(Blessing, 1995)
k = 1616
Tmin = 0.888, Tmax = 1.0l = 1715
10832 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 0.83 w = 1/[σ2(Fo2) + (0.0338P)2]
where P = (Fo2 + 2Fc2)/3
1471 reflections(Δ/σ)max = 0.001
161 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used.

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)
O10.5884 (3)0.79701 (15)0.55668 (14)0.0230 (5)
H1O0.634 (4)0.738 (2)0.565 (2)0.042 (11)*
O20.0327 (2)1.02666 (13)0.55995 (12)0.0206 (5)
O30.0655 (2)0.95532 (13)0.75192 (13)0.0243 (5)
O40.2668 (2)0.88160 (13)0.85230 (13)0.0195 (4)
O50.4936 (2)0.73086 (12)0.74610 (14)0.0210 (4)
N10.2901 (3)0.89387 (19)0.45393 (16)0.0201 (6)
H1N0.260 (4)0.955 (2)0.4238 (18)0.030 (9)*
H2N0.417 (4)0.8732 (18)0.4342 (18)0.024 (8)*
C10.3101 (3)0.90941 (19)0.55718 (18)0.0169 (6)
H10.40120.96920.56900.020*
C20.1082 (4)0.9329 (2)0.60104 (18)0.0178 (6)
H20.01450.87470.58710.021*
C30.1251 (4)0.9470 (2)0.70797 (18)0.0167 (6)
H30.20251.01150.72120.020*
C40.2282 (4)0.85637 (18)0.75510 (19)0.0166 (6)
H40.13700.79530.75310.020*
C50.4233 (4)0.82663 (19)0.70784 (19)0.0164 (6)
H50.52410.88190.72010.020*
C60.3999 (4)0.8123 (2)0.60163 (18)0.0172 (7)
H60.31180.75150.58880.021*
C70.1342 (4)1.0133 (2)0.49823 (19)0.0306 (8)
H7A0.09350.97360.44220.046*0.79 (3)
H7B0.18381.08130.47830.046*0.79 (3)
H7C0.23970.97600.53180.046*0.79 (3)
H7D0.25121.04690.52600.046*0.21 (3)
H7E0.16080.93930.48990.046*0.21 (3)
H7F0.10501.04460.43640.046*0.21 (3)
C80.1531 (4)1.0560 (2)0.7529 (2)0.0304 (7)
H8A0.05491.10660.77490.046*
H8B0.26781.05620.79580.046*
H8C0.19671.07420.68870.046*
C90.1640 (4)0.8206 (2)0.92037 (19)0.0349 (8)
H9A0.02050.83190.91380.052*
H9B0.20640.84060.98430.052*
H9C0.19410.74730.90990.052*
C100.6464 (4)0.7407 (2)0.8146 (2)0.0375 (9)
H10A0.75460.78280.78850.056*
H10B0.69710.67200.83120.056*
H10C0.59310.77430.87160.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0244 (11)0.0199 (13)0.0247 (13)0.0049 (9)0.0085 (9)0.0011 (10)
O20.0216 (10)0.0187 (11)0.0214 (12)0.0015 (8)0.0044 (8)0.0047 (9)
O30.0272 (10)0.0208 (11)0.0248 (11)0.0083 (8)0.0110 (9)0.0045 (10)
O40.0277 (11)0.0198 (10)0.0109 (11)0.0028 (8)0.0003 (8)0.0003 (9)
O50.0261 (10)0.0162 (10)0.0208 (12)0.0026 (8)0.0066 (9)0.0029 (9)
N10.0289 (14)0.0182 (15)0.0132 (15)0.0003 (11)0.0021 (11)0.0028 (12)
C10.0209 (14)0.0159 (16)0.0140 (17)0.0055 (11)0.0000 (12)0.0016 (13)
C20.0184 (15)0.0159 (16)0.0191 (17)0.0012 (11)0.0017 (11)0.0006 (12)
C30.0218 (15)0.0118 (16)0.0166 (17)0.0033 (11)0.0013 (12)0.0003 (13)
C40.0242 (14)0.0110 (14)0.0146 (16)0.0036 (11)0.0012 (13)0.0006 (13)
C50.0195 (14)0.0133 (15)0.0163 (17)0.0022 (11)0.0002 (12)0.0024 (12)
C60.0209 (15)0.0146 (16)0.0160 (17)0.0005 (11)0.0006 (12)0.0005 (13)
C70.0283 (17)0.033 (2)0.031 (2)0.0011 (14)0.0065 (13)0.0087 (15)
C80.0387 (17)0.0262 (18)0.0264 (17)0.0170 (13)0.0090 (15)0.0018 (16)
C90.052 (2)0.0359 (19)0.0164 (19)0.0161 (15)0.0022 (15)0.0025 (15)
C100.0384 (19)0.034 (2)0.040 (2)0.0076 (15)0.0189 (15)0.0037 (15)
Geometric parameters (Å, º) top
O1—C61.431 (3)C4—C51.521 (3)
O1—H1O0.83 (3)C4—H41.0000
O2—C71.430 (3)C5—C61.516 (3)
O2—C21.436 (3)C5—H51.0000
O3—C81.428 (3)C6—H61.0000
O3—C31.428 (3)C7—H7A0.9800
O4—C91.421 (3)C7—H7B0.9800
O4—C41.432 (3)C7—H7C0.9800
O5—C101.415 (3)C7—H7D0.9800
O5—C51.430 (3)C7—H7E0.9800
N1—C11.475 (3)C7—H7F0.9800
N1—H1N0.92 (3)C8—H8A0.9800
N1—H2N0.94 (3)C8—H8B0.9800
C1—C21.523 (3)C8—H8C0.9800
C1—C61.527 (3)C9—H9A0.9800
C1—H11.0000C9—H9B0.9800
C2—C31.522 (3)C9—H9C0.9800
C2—H21.0000C10—H10A0.9800
C3—C41.515 (3)C10—H10B0.9800
C3—H31.0000C10—H10C0.9800
C6—O1—H1O113 (2)C5—C6—H6109.7
C7—O2—C2114.90 (19)C1—C6—H6109.7
C8—O3—C3116.3 (2)O2—C7—H7A109.5
C9—O4—C4115.56 (19)O2—C7—H7B109.5
C10—O5—C5114.77 (19)H7A—C7—H7B109.5
C1—N1—H1N111.0 (16)O2—C7—H7C109.5
C1—N1—H2N104.4 (15)H7A—C7—H7C109.5
H1N—N1—H2N108 (2)H7B—C7—H7C109.5
N1—C1—C2110.2 (2)O2—C7—H7D109.5
N1—C1—C6109.2 (2)H7A—C7—H7D141.1
C2—C1—C6110.5 (2)H7B—C7—H7D56.3
N1—C1—H1109.0H7C—C7—H7D56.3
C2—C1—H1109.0O2—C7—H7E109.5
C6—C1—H1109.0H7A—C7—H7E56.3
O2—C2—C3108.9 (2)H7B—C7—H7E141.1
O2—C2—C1108.7 (2)H7C—C7—H7E56.3
C3—C2—C1111.0 (2)H7D—C7—H7E109.5
O2—C2—H2109.4O2—C7—H7F109.5
C3—C2—H2109.4H7A—C7—H7F56.3
C1—C2—H2109.4H7B—C7—H7F56.3
O3—C3—C4106.2 (2)H7C—C7—H7F141.1
O3—C3—C2111.8 (2)H7D—C7—H7F109.5
C4—C3—C2112.0 (2)H7E—C7—H7F109.5
O3—C3—H3108.9O3—C8—H8A109.5
C4—C3—H3108.9O3—C8—H8B109.5
C2—C3—H3108.9H8A—C8—H8B109.5
O4—C4—C3109.0 (2)O3—C8—H8C109.5
O4—C4—C5108.66 (19)H8A—C8—H8C109.5
C3—C4—C5113.5 (2)H8B—C8—H8C109.5
O4—C4—H4108.5O4—C9—H9A109.5
C3—C4—H4108.5O4—C9—H9B109.5
C5—C4—H4108.5H9A—C9—H9B109.5
O5—C5—C6107.5 (2)O4—C9—H9C109.5
O5—C5—C4109.8 (2)H9A—C9—H9C109.5
C6—C5—C4111.9 (2)H9B—C9—H9C109.5
O5—C5—H5109.2O5—C10—H10A109.5
C6—C5—H5109.2O5—C10—H10B109.5
C4—C5—H5109.2H10A—C10—H10B109.5
O1—C6—C5111.2 (2)O5—C10—H10C109.5
O1—C6—C1106.4 (2)H10A—C10—H10C109.5
C5—C6—C1110.2 (2)H10B—C10—H10C109.5
O1—C6—H6109.7
C7—O2—C2—C3128.9 (2)C2—C3—C4—C549.8 (3)
C7—O2—C2—C1110.0 (2)C10—O5—C5—C6137.0 (2)
N1—C1—C2—O261.4 (3)C10—O5—C5—C4101.0 (3)
C6—C1—C2—O2177.8 (2)O4—C4—C5—O568.1 (2)
N1—C1—C2—C3178.9 (2)C3—C4—C5—O5170.4 (2)
C6—C1—C2—C358.1 (3)O4—C4—C5—C6172.57 (19)
C8—O3—C3—C4152.8 (2)C3—C4—C5—C651.1 (3)
C8—O3—C3—C284.8 (3)O5—C5—C6—O166.5 (3)
O2—C2—C3—O368.2 (2)C4—C5—C6—O1172.81 (19)
C1—C2—C3—O3172.2 (2)O5—C5—C6—C1175.7 (2)
O2—C2—C3—C4172.73 (19)C4—C5—C6—C155.1 (3)
C1—C2—C3—C453.1 (3)N1—C1—C6—O159.0 (3)
C9—O4—C4—C3115.0 (2)C2—C1—C6—O1179.6 (2)
C9—O4—C4—C5120.8 (2)N1—C1—C6—C5179.6 (2)
O3—C3—C4—O466.6 (2)C2—C1—C6—C559.0 (3)
C2—C3—C4—O4171.06 (19)C8—O3—C3—H336
O3—C3—C4—C5172.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.92 (3)2.35 (3)3.258 (3)171 (2)
O1—H1O···N1ii0.83 (3)2.02 (3)2.819 (3)162 (3)
C10—H10A···O3iii0.982.593.496 (3)154
Symmetry codes: (i) x+1/2, y+2, z1/2; (ii) x+1/2, y+3/2, z+1; (iii) x+1, y, z.
 

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