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The title compound, C6H10N2O8·2H2O, involves a cyclo­hexane with four hydroxyl and two nitro group substituents. In the crystal form reported here, the mol­ecules lie across crystallographic inversion centres. The crystal structure contains an extensive network of hydrogen bonding between the hydroxyl and nitro groups and the water mol­ecules. The water mol­ecule is involved in every hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016532/ci6245sup1.cif
Contains datablocks clc33m, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016532/ci6245Isup2.hkl
Contains datablock I

CCDC reference: 221718

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2,3,5,6-tetrahydroxy-1,4-dinitrocyclohexane dihydrate top
Crystal data top
C6H10N2O8·2H2OZ = 1
Mr = 274.19F(000) = 144
Triclinic, P1Dx = 1.674 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.7309 (5) ÅCell parameters from 1494 reflections
b = 7.8835 (9) Åθ = 2.5–28.2°
c = 8.0592 (9) ŵ = 0.16 mm1
α = 65.180 (2)°T = 93 K
β = 86.143 (2)°Prism, colorless
γ = 85.995 (2)°0.60 × 0.12 × 0.08 mm
V = 271.91 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1288 independent reflections
Radiation source: fine-focus sealed tube1075 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 28.2°, θmin = 2.8°
Absorption correction: multi-scan
(SABABS; Bruker, 2001)
h = 65
Tmin = 0.830, Tmax = 0.981k = 1010
2086 measured reflectionsl = 1010
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.061P)2 + 0.05P]
where P = (Fo2 + 2Fc2)/3
1288 reflections(Δ/σ)max < 0.001
94 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.23 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
C10.4621 (3)0.0855 (2)0.1334 (2)0.0119 (3)
H1A0.54940.12820.21810.014*
O10.1624 (2)0.10772 (17)0.14720 (16)0.0148 (3)
H1H0.121 (4)0.207 (3)0.167 (3)0.022*
C20.5768 (3)0.1966 (2)0.0627 (2)0.0120 (3)
H2A0.78870.18400.06660.014*
O20.4895 (2)0.38755 (16)0.11657 (16)0.0153 (3)
H2H0.626 (5)0.450 (3)0.146 (3)0.023*
C30.4625 (3)0.1227 (2)0.1897 (2)0.0125 (3)
H3A0.25140.14260.19030.015*
N30.5841 (3)0.22559 (19)0.38254 (18)0.0143 (3)
O3A0.8056 (2)0.30722 (17)0.40633 (16)0.0203 (3)
O3B0.4568 (2)0.21747 (18)0.50704 (16)0.0217 (3)
O1W0.0215 (2)0.41843 (17)0.21501 (18)0.0149 (3)
H1W0.128 (5)0.476 (3)0.172 (3)0.022*
H2W0.015 (4)0.391 (3)0.324 (3)0.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0107 (6)0.0133 (7)0.0137 (8)0.0024 (5)0.0010 (5)0.0075 (6)
O10.0109 (5)0.0159 (6)0.0200 (6)0.0010 (4)0.0025 (4)0.0102 (5)
C20.0108 (6)0.0111 (7)0.0150 (8)0.0022 (5)0.0020 (5)0.0064 (6)
O20.0140 (5)0.0105 (6)0.0208 (6)0.0028 (4)0.0020 (4)0.0061 (5)
C30.0123 (6)0.0140 (8)0.0101 (7)0.0019 (6)0.0021 (5)0.0042 (6)
N30.0159 (6)0.0142 (7)0.0127 (7)0.0004 (5)0.0002 (5)0.0058 (6)
O3A0.0190 (6)0.0237 (7)0.0175 (6)0.0095 (5)0.0049 (4)0.0075 (5)
O3B0.0243 (6)0.0276 (7)0.0139 (6)0.0036 (5)0.0017 (5)0.0087 (5)
O1W0.0141 (5)0.0158 (6)0.0144 (6)0.0002 (4)0.0013 (4)0.0064 (5)
Geometric parameters (Å, º) top
C1—O11.4192 (17)O2—H2H0.80 (2)
C1—C3i1.530 (2)C3—N31.5136 (19)
C1—C21.532 (2)C3—C1i1.530 (2)
C1—H1A1.00C3—H3A1.00
O1—H1H0.87 (2)N3—O3A1.2300 (17)
C2—O21.4188 (18)N3—O3B1.2303 (18)
C2—C31.517 (2)O1W—H1W0.83 (2)
C2—H2A1.00O1W—H2W0.82 (2)
O1—C1—C3i107.68 (11)C1—C2—H2A109.5
O1—C1—C2111.37 (12)C2—O2—H2H109.5 (15)
C3i—C1—C2109.11 (11)N3—C3—C2110.44 (12)
O1—C1—H1A109.6N3—C3—C1i106.86 (11)
C3i—C1—H1A109.6C2—C3—C1i112.84 (12)
C2—C1—H1A109.6N3—C3—H3A108.9
C1—O1—H1H108.3 (14)C2—C3—H3A108.9
O2—C2—C3110.27 (12)C1i—C3—H3A108.9
O2—C2—C1108.29 (11)O3A—N3—O3B123.73 (13)
C3—C2—C1109.83 (12)O3A—N3—C3119.12 (12)
O2—C2—H2A109.5O3B—N3—C3117.12 (12)
C3—C2—H2A109.5H1W—O1W—H2W99.4 (19)
O1—C1—C2—O257.59 (15)O2—C2—C3—C1i177.30 (11)
C3i—C1—C2—O2176.31 (11)C1—C2—C3—C1i58.03 (15)
O1—C1—C2—C362.89 (15)C2—C3—N3—O3A21.12 (18)
C3i—C1—C2—C355.83 (16)C1i—C3—N3—O3A101.96 (15)
O2—C2—C3—N363.18 (14)C2—C3—N3—O3B160.94 (12)
C1—C2—C3—N3177.56 (11)C1i—C3—N3—O3B75.98 (15)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1H···O1W0.87 (2)1.89 (2)2.7549 (16)178 (2)
O2—H2H···O1Wii0.80 (2)1.95 (2)2.7478 (16)175 (2)
O1W—H1W···O2iii0.83 (2)1.93 (2)2.7450 (16)169 (2)
O1W—H2W···O3Aiv0.82 (2)2.12 (2)2.9299 (17)168 (2)
Symmetry codes: (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x1, y, z+1.
 

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