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The structure of N-iso­propyl-D-glycero-D-gulo-hepton­amide, C10H21NO7, shows a bent C chain conformation in the glucoheptonic acid moiety. The crystal packing comprises a two-dimensional arrangement of intermolecular hydrogen bonds involving all O atoms. A feature of the crystal packing is a hydrogen-bonded (OH)4 ring, which might be responsible for the observed conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011821/tk6166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011821/tk6166Isup2.hkl
Contains datablock I

CCDC reference: 242343

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.113
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 27.30 From the CIF: _reflns_number_total 1504 Count of symmetry unique reflns 1520 Completeness (_total/calc) 98.95% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker 2000a); cell refinement: SMART; data reduction: SAINT (Bruker 2000b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2000c); software used to prepare material for publication: SHELXTL and enCIFer v1.1 (Allen et al. 2004).

N-isopropyl-D-glycero-D-gulo-heptonamide top
Crystal data top
C10H21NO7F(000) = 288
Mr = 267.28Dx = 1.346 Mg m3
Monoclinic, P21Melting point: 534 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 4.866 (2) ÅCell parameters from 1024 reflections
b = 22.435 (9) Åθ = 3.5–27.3°
c = 6.040 (2) ŵ = 0.11 mm1
β = 90.664 (7)°T = 293 K
V = 659.3 (5) Å3Trigonal prismatic, colorless
Z = 20.40 × 0.20 × 0.05 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.3°, θmin = 1.8°
φ and ω scansh = 66
3915 measured reflectionsk = 2824
1504 independent reflectionsl = 76
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0755P)2]
where P = (Fo2 + 2Fc2)/3
1504 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.18 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
C10.1920 (6)0.37616 (12)0.1509 (4)0.0347 (6)
C20.0042 (6)0.40484 (13)0.0215 (5)0.0351 (6)
C30.1732 (6)0.44277 (13)0.1800 (4)0.0312 (6)
C40.3208 (6)0.49653 (12)0.0772 (4)0.0306 (6)
C50.1398 (5)0.53999 (11)0.0456 (4)0.0284 (5)
C60.3119 (6)0.58734 (12)0.1655 (4)0.0322 (6)
C70.1397 (6)0.63217 (13)0.2891 (5)0.0393 (7)
C80.3943 (8)0.28165 (14)0.2836 (6)0.0473 (8)
C90.4991 (11)0.2294 (2)0.1520 (7)0.0738 (13)
H9A0.63250.20790.23880.089*
H9B0.58290.24370.01890.089*
H9C0.34870.20350.11440.089*
C100.2483 (11)0.26276 (18)0.4913 (7)0.0716 (12)
H10A0.17030.29710.56140.086*
H10B0.37710.24410.59090.086*
H10C0.10470.23510.45380.086*
N10.2133 (6)0.31719 (12)0.1412 (4)0.0420 (6)
O10.3181 (6)0.40739 (10)0.2843 (3)0.0533 (6)
O20.1400 (4)0.35979 (10)0.1387 (4)0.0479 (6)
O30.3726 (4)0.40529 (10)0.2765 (3)0.0418 (5)
O40.4498 (4)0.52732 (10)0.2547 (3)0.0384 (5)
O50.0524 (4)0.56883 (8)0.1012 (3)0.0331 (4)
O60.5062 (4)0.55920 (10)0.3101 (3)0.0387 (5)
O70.0088 (4)0.60602 (10)0.4627 (3)0.0399 (5)
H20.12800.43000.04150.048*
H30.05040.45620.28440.048*
H40.46010.48440.01300.048*
H50.03290.51880.14920.048*
H60.42090.60690.04500.048*
H7A0.00930.65130.18580.048*
H7B0.25840.65740.34780.048*
H80.54410.30640.31600.048*
H1N0.13810.30180.04460.060*
H2O0.28940.37330.16740.060*
H3O0.36440.41070.39320.060*
H4O0.60340.53770.21230.060*
H5O0.01720.57670.21110.060*
H6O0.43090.54620.40590.060*
H7O0.16500.59700.42420.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0489 (16)0.0329 (14)0.0224 (12)0.0018 (12)0.0059 (10)0.0004 (10)
C20.0340 (14)0.0325 (13)0.0387 (14)0.0058 (12)0.0006 (10)0.0052 (12)
C30.0346 (14)0.0375 (13)0.0213 (12)0.0100 (11)0.0050 (9)0.0015 (10)
C40.0297 (13)0.0410 (15)0.0210 (12)0.0024 (11)0.0009 (9)0.0032 (10)
C50.0292 (13)0.0348 (13)0.0210 (12)0.0016 (11)0.0020 (9)0.0048 (10)
C60.0349 (14)0.0381 (14)0.0235 (12)0.0090 (11)0.0021 (10)0.0060 (10)
C70.0483 (18)0.0347 (14)0.0349 (15)0.0082 (13)0.0015 (12)0.0037 (12)
C80.057 (2)0.0353 (15)0.0492 (18)0.0072 (14)0.0118 (15)0.0019 (14)
C90.090 (3)0.064 (2)0.067 (3)0.035 (2)0.009 (2)0.005 (2)
C100.115 (4)0.051 (2)0.050 (2)0.012 (2)0.003 (2)0.0111 (17)
N10.0528 (15)0.0330 (12)0.0400 (13)0.0044 (12)0.0085 (11)0.0018 (11)
O10.0947 (18)0.0392 (11)0.0256 (10)0.0024 (12)0.0121 (10)0.0013 (10)
O20.0382 (12)0.0380 (11)0.0672 (16)0.0066 (9)0.0160 (10)0.0073 (10)
O30.0482 (11)0.0568 (13)0.0203 (8)0.0204 (10)0.0020 (7)0.0044 (9)
O40.0341 (10)0.0594 (13)0.0216 (9)0.0052 (9)0.0015 (7)0.0068 (8)
O50.0311 (9)0.0422 (10)0.0262 (9)0.0018 (8)0.0005 (7)0.0052 (8)
O60.0335 (10)0.0591 (12)0.0233 (10)0.0070 (9)0.0001 (7)0.0042 (8)
O70.0359 (11)0.0569 (13)0.0270 (10)0.0029 (9)0.0014 (8)0.0022 (9)
Geometric parameters (Å, º) top
C1—O11.227 (3)C7—H7A1.0434
C1—N11.328 (4)C7—H7B0.8795
C1—C21.521 (4)C8—N11.461 (4)
C2—O21.415 (3)C8—C91.508 (5)
C2—C31.528 (4)C8—C101.510 (6)
C2—H20.9393C8—H80.9348
C3—O31.414 (3)C9—H9A0.9600
C3—C41.532 (4)C9—H9B0.9600
C3—H30.9148C9—H9C0.9600
C4—O41.427 (3)C10—H10A0.9600
C4—C51.514 (4)C10—H10B0.9600
C4—H40.9061C10—H10C0.9600
C5—O51.435 (3)N1—H1N0.7671
C5—C61.530 (4)O2—H2O0.8044
C5—H50.9468O3—H3O0.7159
C6—O61.427 (3)O4—H4O0.8214
C6—C71.512 (4)O5—H5O0.7687
C6—H61.0056O6—H6O0.7471
C7—O71.408 (4)O7—H7O0.8180
O1—C1—N1124.0 (3)O7—C7—C6112.5 (2)
O1—C1—C2120.0 (2)O7—C7—H7A104.9
N1—C1—C2116.0 (2)C6—C7—H7A111.3
O2—C2—C1109.3 (2)O7—C7—H7B107.9
O2—C2—C3110.6 (2)C6—C7—H7B105.2
C1—C2—C3109.9 (2)H7A—C7—H7B115.2
O2—C2—H2107.1N1—C8—C9108.6 (3)
C1—C2—H2112.6N1—C8—C10110.9 (3)
C3—C2—H2107.2C9—C8—C10112.7 (3)
O3—C3—C2107.7 (2)N1—C8—H8105.2
O3—C3—C4108.3 (2)C9—C8—H8107.6
C2—C3—C4116.0 (2)C10—C8—H8111.5
O3—C3—H3111.0C8—C9—H9A109.5
C2—C3—H3105.3C8—C9—H9B109.5
C4—C3—H3108.6H9A—C9—H9B109.5
O4—C4—C5108.6 (2)C8—C9—H9C109.5
O4—C4—C3106.5 (2)H9A—C9—H9C109.5
C5—C4—C3115.7 (2)H9B—C9—H9C109.5
O4—C4—H4105.4C8—C10—H10A109.5
C5—C4—H4109.6C8—C10—H10B109.5
C3—C4—H4110.5H10A—C10—H10B109.5
O5—C5—C4111.5 (2)C8—C10—H10C109.5
O5—C5—C6109.2 (2)H10A—C10—H10C109.5
C4—C5—C6111.1 (2)H10B—C10—H10C109.5
O5—C5—H5106.0C1—N1—C8124.4 (3)
C4—C5—H5109.1C1—N1—H1N116.4
C6—C5—H5109.8C8—N1—H1N118.8
O6—C6—C7111.0 (2)C2—O2—H2O106.2
O6—C6—C5109.7 (2)C3—O3—H3O106.0
C7—C6—C5113.1 (2)C4—O4—H4O108.0
O6—C6—H6106.5C5—O5—H5O110.2
C7—C6—H6111.6C6—O6—H6O108.6
C5—C6—H6104.5C7—O7—H7O112.0
O1—C1—C2—O2173.6 (3)C3—C4—C5—O565.1 (3)
N1—C1—C2—O28.3 (3)O4—C4—C5—C667.5 (2)
O1—C1—C2—C364.8 (3)C3—C4—C5—C6172.9 (2)
N1—C1—C2—C3113.3 (3)O5—C5—C6—O6179.30 (19)
O2—C2—C3—O363.4 (3)C4—C5—C6—O655.9 (2)
C1—C2—C3—O357.4 (3)O5—C5—C6—C756.1 (3)
O2—C2—C3—C4175.1 (2)C4—C5—C6—C7179.5 (2)
C1—C2—C3—C464.1 (3)O6—C6—C7—O759.7 (3)
O3—C3—C4—O462.4 (2)C5—C6—C7—O764.2 (3)
C2—C3—C4—O4176.4 (2)O1—C1—N1—C81.6 (5)
O3—C3—C4—C5176.7 (2)C2—C1—N1—C8176.5 (3)
C2—C3—C4—C555.6 (3)C9—C8—N1—C1145.4 (4)
O4—C4—C5—O554.6 (3)C10—C8—N1—C190.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.772.172.581 (3)114
O5—H5O···O40.772.402.784 (3)113
O6—H6O···O70.752.552.878 (3)109
O2—H2O···O3i0.801.912.704 (3)172
O3—H3O···O1ii0.721.962.663 (3)168
O4—H4O···O5iii0.821.932.746 (3)175
O5—H5O···O7ii0.772.082.773 (3)150
O6—H6O···O4iv0.752.092.741 (3)145
O7—H7O···O6i0.821.932.734 (3)167
Symmetry codes: (i) x1, y, z; (ii) x, y, z1; (iii) x+1, y, z; (iv) x, y, z+1.
Deviations from the plane 07-06i-05ii-04iii for the atoms present in the (OH)4 ringa (Å) top
070.0324 (11)H7O0.1427 (13)C7-0.004 (4)
O6i-0.0328 (11)H6Oi0.0012 (28)C6i0.749 (4)
O5ii-0.0323 (11)H5Oii-0.1727 (18)C5ii-0.820 (4)
O4iii0.0327 (11)H4Oiii-0.0405 (28)C4iii-0.059 (4)
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1; (iii) x-1, y, z+1. Note: (a) Rms deviation of fitted atoms = 0.033.
 

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