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In the title compound, C10H22NO6+·C6H2N3O7-, the cyclo­hexane ring has a slightly distorted chair conformation. Molecules are linked into chains by hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012419/fl6157sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012419/fl6157Isup2.hkl
Contains datablock I

CCDC reference: 271876

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.103
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.84 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4
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 27.03 From the CIF: _reflns_number_total 2383 Count of symmetry unique reflns 2394 Completeness (_total/calc) 99.54% 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 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(+)-(1S,2S,3S,4R,5R)-N-(1,3-Dihydroxyprop-2-yl)-2,3,4-trihydroxy- 5-(hydroxymethyl)-1-cyclohexanaminium picrate top
Crystal data top
C10H22NO6+·C6H2N3O7F(000) = 504
Mr = 480.39Dx = 1.586 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 966 reflections
a = 8.7362 (11) Åθ = 3.2–26.8°
b = 6.8235 (8) ŵ = 0.14 mm1
c = 16.957 (2) ÅT = 293 K
β = 95.769 (2)°Block, yellow
V = 1005.7 (2) Å30.33 × 0.25 × 0.19 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD
diffractometer
2383 independent reflections
Radiation source: fine-focus sealed tube2138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1011
Tmin = 0.884, Tmax = 0.974k = 87
6583 measured reflectionsl = 2121
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2641P]
where P = (Fo2 + 2Fc2)/3
2383 reflections(Δ/σ)max = 0.006
304 parametersΔρmax = 0.41 e Å3
7 restraintsΔρmin = 0.27 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
C10.1457 (3)0.4600 (4)0.17641 (14)0.0292 (5)
H10.16770.51530.22970.035*
C20.1553 (3)0.6253 (4)0.11585 (14)0.0292 (5)
H20.25430.69260.12680.035*
C30.1422 (3)0.5455 (4)0.03067 (13)0.0266 (5)
H30.04370.47670.02090.032*
C40.2704 (3)0.3976 (4)0.02347 (14)0.0288 (5)
H40.36820.46440.03890.035*
C50.2589 (3)0.2261 (4)0.08035 (15)0.0299 (5)
H5A0.16060.15920.06640.036*
C60.2628 (3)0.2994 (5)0.16567 (14)0.0328 (6)
H6A0.24340.18990.19980.039*
H6B0.36500.34890.18240.039*
C70.0920 (3)0.3454 (5)0.24305 (14)0.0337 (6)
H70.07540.45980.27780.040*
C80.0211 (4)0.1681 (5)0.28631 (15)0.0397 (7)
H8A0.08690.19280.30210.048*
H8B0.07170.14510.33390.048*
C90.2638 (3)0.3258 (6)0.21829 (17)0.0430 (7)
H9A0.28340.20500.18880.052*
H9B0.31890.32010.26510.052*
C100.3889 (3)0.0791 (4)0.07363 (17)0.0356 (6)
H10A0.48560.14930.07500.043*
H10B0.39500.00820.11900.043*
C110.2983 (3)0.2813 (4)0.63925 (15)0.0361 (6)
C120.2020 (3)0.2824 (5)0.56480 (17)0.0437 (7)
C130.2573 (4)0.2997 (5)0.49253 (17)0.0501 (8)
H130.18960.30490.44660.060*
C140.4129 (4)0.3093 (5)0.48800 (16)0.0454 (7)
C150.5167 (4)0.3100 (5)0.55580 (16)0.0400 (6)
H150.62200.31880.55230.048*
C160.4589 (3)0.2972 (4)0.62796 (15)0.0361 (6)
O130.2480 (2)0.2740 (4)0.70600 (11)0.0459 (5)
N10.0189 (2)0.3849 (4)0.16770 (12)0.0289 (5)
H1A0.07770.47290.13910.035*
H1B0.02140.27300.13950.035*
N20.0343 (3)0.2637 (6)0.56562 (19)0.0616 (9)
N30.4723 (5)0.3204 (6)0.41135 (16)0.0643 (9)
N40.5720 (3)0.3039 (5)0.69756 (14)0.0450 (6)
O10.0346 (2)0.7629 (3)0.12117 (11)0.0404 (5)
H1C0.05420.83150.16060.061*
O20.1443 (2)0.6993 (3)0.02586 (10)0.0351 (4)
H2A0.21610.77360.01270.053*
O30.2735 (2)0.3321 (4)0.05605 (10)0.0409 (5)
H3A0.18520.32340.07730.061*
O40.3681 (2)0.0348 (3)0.00280 (12)0.0395 (5)
H4A0.35350.03840.03560.059*
O50.0362 (3)0.0001 (3)0.23740 (12)0.0437 (5)
H50.09800.07570.25420.066*
O60.3177 (3)0.4873 (4)0.17053 (12)0.0486 (6)
H6C0.33280.58100.19900.073*
O70.0172 (3)0.1647 (7)0.61563 (17)0.0829 (11)
O80.0457 (4)0.3472 (10)0.5156 (3)0.145 (2)
O90.3797 (4)0.3431 (7)0.35258 (14)0.0988 (13)
O100.6105 (4)0.3101 (7)0.40870 (16)0.0864 (10)
O110.6939 (3)0.3832 (6)0.69244 (17)0.0843 (12)
O120.5427 (3)0.2238 (6)0.75837 (14)0.0756 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0280 (12)0.0360 (14)0.0231 (10)0.0061 (11)0.0005 (9)0.0000 (11)
C20.0274 (12)0.0318 (13)0.0278 (11)0.0032 (10)0.0004 (9)0.0010 (10)
C30.0240 (11)0.0302 (12)0.0253 (11)0.0036 (9)0.0014 (8)0.0034 (10)
C40.0258 (11)0.0344 (13)0.0259 (11)0.0017 (10)0.0016 (9)0.0009 (10)
C50.0236 (11)0.0329 (14)0.0326 (12)0.0009 (10)0.0007 (9)0.0020 (11)
C60.0298 (12)0.0395 (15)0.0283 (11)0.0008 (11)0.0010 (9)0.0063 (12)
C70.0382 (13)0.0400 (15)0.0245 (11)0.0063 (12)0.0117 (10)0.0036 (11)
C80.0470 (16)0.0468 (18)0.0257 (12)0.0054 (14)0.0059 (11)0.0017 (12)
C90.0385 (15)0.0516 (18)0.0409 (14)0.0026 (14)0.0132 (11)0.0030 (15)
C100.0298 (13)0.0346 (15)0.0416 (14)0.0013 (11)0.0002 (10)0.0019 (12)
C110.0412 (14)0.0330 (14)0.0330 (12)0.0053 (12)0.0013 (10)0.0008 (12)
C120.0449 (16)0.0432 (17)0.0410 (14)0.0021 (14)0.0059 (12)0.0049 (14)
C130.066 (2)0.0474 (18)0.0334 (13)0.0081 (17)0.0107 (13)0.0079 (15)
C140.069 (2)0.0382 (16)0.0293 (12)0.0088 (15)0.0051 (12)0.0014 (13)
C150.0481 (16)0.0344 (15)0.0379 (13)0.0014 (13)0.0072 (12)0.0005 (13)
C160.0419 (14)0.0332 (14)0.0325 (12)0.0010 (12)0.0007 (10)0.0013 (12)
O130.0445 (11)0.0574 (14)0.0361 (10)0.0120 (11)0.0053 (8)0.0037 (10)
N10.0308 (10)0.0338 (12)0.0227 (9)0.0027 (9)0.0048 (7)0.0018 (9)
N20.0471 (16)0.069 (2)0.0645 (18)0.0005 (16)0.0165 (14)0.0181 (18)
N30.101 (3)0.0586 (19)0.0352 (14)0.019 (2)0.0161 (15)0.0004 (15)
N40.0401 (13)0.0552 (16)0.0384 (12)0.0028 (13)0.0020 (10)0.0021 (13)
O10.0485 (11)0.0368 (11)0.0356 (9)0.0082 (9)0.0032 (8)0.0056 (9)
O20.0364 (10)0.0383 (11)0.0298 (9)0.0017 (9)0.0013 (7)0.0090 (9)
O30.0435 (11)0.0514 (12)0.0281 (9)0.0061 (11)0.0060 (8)0.0020 (9)
O40.0371 (10)0.0376 (11)0.0447 (10)0.0031 (9)0.0082 (8)0.0006 (9)
O50.0496 (12)0.0406 (12)0.0434 (11)0.0024 (10)0.0170 (9)0.0048 (10)
O60.0463 (12)0.0588 (15)0.0412 (11)0.0114 (12)0.0072 (9)0.0007 (11)
O70.0517 (15)0.131 (3)0.0652 (16)0.0129 (19)0.0001 (12)0.019 (2)
O80.068 (2)0.195 (5)0.165 (4)0.007 (3)0.032 (2)0.108 (4)
O90.138 (3)0.125 (3)0.0306 (12)0.044 (3)0.0038 (15)0.0111 (18)
O100.105 (3)0.104 (3)0.0566 (15)0.009 (2)0.0374 (16)0.0035 (19)
O110.0512 (14)0.135 (3)0.0651 (15)0.0321 (19)0.0026 (12)0.006 (2)
O120.0600 (15)0.119 (3)0.0441 (13)0.0126 (18)0.0140 (11)0.0231 (16)
Geometric parameters (Å, º) top
C1—N11.520 (3)C10—H10A0.9700
C1—C61.523 (4)C10—H10B0.9700
C1—C21.534 (4)C11—O131.256 (3)
C1—H10.9800C11—C161.440 (4)
C2—O11.421 (3)C11—C121.445 (4)
C2—C31.537 (3)C12—C131.367 (4)
C2—H20.9800C12—N21.471 (4)
C3—O21.423 (3)C13—C141.371 (5)
C3—C41.522 (4)C13—H130.9300
C3—H30.9800C14—C151.391 (4)
C4—O31.423 (3)C14—N31.449 (4)
C4—C51.527 (4)C15—C161.372 (4)
C4—H40.9800C15—H150.9300
C5—C101.528 (4)C16—N41.461 (4)
C5—C61.528 (4)N1—H1A0.9000
C5—H5A0.9800N1—H1B0.9000
C6—H6A0.9700N2—O81.189 (4)
C6—H6B0.9700N2—O71.207 (4)
C7—N11.509 (3)N3—O101.215 (5)
C7—C81.515 (4)N3—O91.229 (4)
C7—C91.523 (4)N4—O111.205 (4)
C7—H70.9800N4—O121.217 (4)
C8—O51.413 (4)O1—H1C0.8200
C8—H8A0.9700O2—H2A0.8200
C8—H8B0.9700O3—H3A0.8200
C9—O61.420 (4)O4—H4A0.8200
C9—H9A0.9700O5—H50.8200
C9—H9B0.9700O6—H6C0.8200
C10—O41.427 (4)
N1—C1—C6112.7 (2)C7—C9—H9A109.5
N1—C1—C2107.34 (19)O6—C9—H9B109.5
C6—C1—C2111.5 (2)C7—C9—H9B109.5
N1—C1—H1108.4H9A—C9—H9B108.1
C6—C1—H1108.4O4—C10—C5112.8 (2)
C2—C1—H1108.4O4—C10—H10A109.0
O1—C2—C1110.6 (2)C5—C10—H10A109.0
O1—C2—C3107.94 (19)O4—C10—H10B109.0
C1—C2—C3111.4 (2)C5—C10—H10B109.0
O1—C2—H2108.9H10A—C10—H10B107.8
C1—C2—H2108.9O13—C11—C16123.8 (2)
C3—C2—H2108.9O13—C11—C12124.2 (3)
O2—C3—C4112.08 (19)C16—C11—C12111.9 (2)
O2—C3—C2111.5 (2)C13—C12—C11123.8 (3)
C4—C3—C2108.94 (19)C13—C12—N2117.3 (3)
O2—C3—H3108.1C11—C12—N2118.9 (3)
C4—C3—H3108.1C12—C13—C14119.8 (3)
C2—C3—H3108.1C12—C13—H13120.1
O3—C4—C3111.6 (2)C14—C13—H13120.1
O3—C4—C5111.5 (2)C13—C14—C15121.4 (3)
C3—C4—C5111.22 (19)C13—C14—N3119.9 (3)
O3—C4—H4107.4C15—C14—N3118.6 (3)
C3—C4—H4107.4C16—C15—C14118.0 (3)
C5—C4—H4107.4C16—C15—H15121.0
C4—C5—C10111.1 (2)C14—C15—H15121.0
C4—C5—C6110.5 (2)C15—C16—C11125.0 (2)
C10—C5—C6109.9 (2)C15—C16—N4116.1 (3)
C4—C5—H5A108.4C11—C16—N4118.9 (2)
C10—C5—H5A108.4C7—N1—C1117.03 (19)
C6—C5—H5A108.4C7—N1—H1A108.0
C1—C6—C5113.4 (2)C1—N1—H1A108.0
C1—C6—H6A108.9C7—N1—H1B108.0
C5—C6—H6A108.9C1—N1—H1B108.0
C1—C6—H6B108.9H1A—N1—H1B107.3
C5—C6—H6B108.9O8—N2—O7122.4 (4)
H6A—C6—H6B107.7O8—N2—C12117.8 (3)
N1—C7—C8111.5 (2)O7—N2—C12119.8 (3)
N1—C7—C9105.7 (2)O10—N3—O9123.6 (3)
C8—C7—C9114.0 (2)O10—N3—C14118.5 (3)
N1—C7—H7108.5O9—N3—C14117.9 (4)
C8—C7—H7108.5O11—N4—O12121.7 (3)
C9—C7—H7108.5O11—N4—C16119.1 (3)
O5—C8—C7110.8 (2)O12—N4—C16119.2 (3)
O5—C8—H8A109.5C2—O1—H1C109.5
C7—C8—H8A109.5C3—O2—H2A109.5
O5—C8—H8B109.5C4—O3—H3A109.5
C7—C8—H8B109.5C10—O4—H4A109.5
H8A—C8—H8B108.1C8—O5—H5109.5
O6—C9—C7110.5 (3)C9—O6—H6C109.5
O6—C9—H9A109.5
N1—C1—C2—O149.8 (3)C16—C11—C12—N2178.9 (3)
C6—C1—C2—O1173.7 (2)C11—C12—C13—C142.6 (6)
N1—C1—C2—C370.3 (2)N2—C12—C13—C14177.3 (3)
C6—C1—C2—C353.6 (3)C12—C13—C14—C152.7 (5)
O1—C2—C3—O255.8 (3)C12—C13—C14—N3177.8 (3)
C1—C2—C3—O2177.42 (19)C13—C14—C15—C161.1 (5)
O1—C2—C3—C4180.0 (2)N3—C14—C15—C16179.3 (3)
C1—C2—C3—C458.3 (3)C14—C15—C16—C110.6 (5)
O2—C3—C4—O350.5 (3)C14—C15—C16—N4178.4 (3)
C2—C3—C4—O3174.4 (2)O13—C11—C16—C15178.4 (3)
O2—C3—C4—C5175.7 (2)C12—C11—C16—C150.6 (5)
C2—C3—C4—C560.4 (3)O13—C11—C16—N40.5 (5)
O3—C4—C5—C1055.4 (3)C12—C11—C16—N4178.3 (3)
C3—C4—C5—C10179.4 (2)C8—C7—N1—C170.2 (3)
O3—C4—C5—C6177.6 (2)C9—C7—N1—C1165.4 (2)
C3—C4—C5—C657.2 (3)C6—C1—N1—C7100.1 (3)
N1—C1—C6—C570.2 (3)C2—C1—N1—C7136.8 (2)
C2—C1—C6—C550.6 (3)C13—C12—N2—O833.1 (6)
C4—C5—C6—C152.1 (3)C11—C12—N2—O8147.0 (5)
C10—C5—C6—C1175.0 (2)C13—C12—N2—O7146.3 (4)
N1—C7—C8—O558.1 (3)C11—C12—N2—O733.7 (5)
C9—C7—C8—O561.5 (3)C13—C14—N3—O10173.1 (4)
N1—C7—C9—O650.6 (3)C15—C14—N3—O107.3 (6)
C8—C7—C9—O6173.4 (2)C13—C14—N3—O98.0 (6)
C4—C5—C10—O473.6 (3)C15—C14—N3—O9171.6 (4)
C6—C5—C10—O4163.8 (2)C15—C16—N4—O1124.8 (5)
O13—C11—C12—C13176.8 (3)C11—C16—N4—O11154.2 (3)
C16—C11—C12—C131.0 (5)C15—C16—N4—O12152.8 (3)
O13—C11—C12—N23.3 (5)C11—C16—N4—O1228.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O60.902.222.707 (3)114
N1—H1A···O10.902.242.751 (3)115
N1—H1B···O2i0.902.172.839 (3)131
O1—H1C···O5ii0.821.962.671 (3)144
O2—H2A···O4ii0.821.862.676 (3)171
O3—H3A···O1i0.822.032.844 (3)171
O4—H4A···O30.822.142.790 (3)136
O4—H4A···O6i0.822.302.932 (3)134
O5—H5···O13iii0.821.842.662 (3)175
O6—H6C···O13iv0.822.152.885 (3)149
O6—H6C···O12iv0.822.262.898 (4)135
Symmetry codes: (i) x, y1/2, z; (ii) x, y+1, z; (iii) x, y1/2, z+1; (iv) x, y+1/2, z+1.
 

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