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
CCDC reference: 221718
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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
C6H10N2O8·2H2O | Z = 1 |
Mr = 274.19 | F(000) = 144 |
Triclinic, P1 | Dx = 1.674 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7309 (5) Å | Cell parameters from 1494 reflections |
b = 7.8835 (9) Å | θ = 2.5–28.2° |
c = 8.0592 (9) Å | µ = 0.16 mm−1 |
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 tube | 1075 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 28.2°, θmin = 2.8° |
Absorption correction: multi-scan (SABABS; Bruker, 2001) | h = −6→5 |
Tmin = 0.830, Tmax = 0.981 | k = −10→10 |
2086 measured reflections | l = −10→10 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H 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 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4621 (3) | 0.0855 (2) | 0.1334 (2) | 0.0119 (3) | |
H1A | 0.5494 | 0.1282 | 0.2181 | 0.014* | |
O1 | 0.1624 (2) | 0.10772 (17) | 0.14720 (16) | 0.0148 (3) | |
H1H | 0.121 (4) | 0.207 (3) | 0.167 (3) | 0.022* | |
C2 | 0.5768 (3) | 0.1966 (2) | −0.0627 (2) | 0.0120 (3) | |
H2A | 0.7887 | 0.1840 | −0.0666 | 0.014* | |
O2 | 0.4895 (2) | 0.38755 (16) | −0.11657 (16) | 0.0153 (3) | |
H2H | 0.626 (5) | 0.450 (3) | −0.146 (3) | 0.023* | |
C3 | 0.4625 (3) | 0.1227 (2) | −0.1897 (2) | 0.0125 (3) | |
H3A | 0.2514 | 0.1426 | −0.1903 | 0.015* | |
N3 | 0.5841 (3) | 0.22559 (19) | −0.38254 (18) | 0.0143 (3) | |
O3A | 0.8056 (2) | 0.30722 (17) | −0.40633 (16) | 0.0203 (3) | |
O3B | 0.4568 (2) | 0.21747 (18) | −0.50704 (16) | 0.0217 (3) | |
O1W | 0.0215 (2) | 0.41843 (17) | 0.21501 (18) | 0.0149 (3) | |
H1W | −0.128 (5) | 0.476 (3) | 0.172 (3) | 0.022* | |
H2W | −0.015 (4) | 0.391 (3) | 0.324 (3) | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0107 (6) | 0.0133 (7) | 0.0137 (8) | −0.0024 (5) | 0.0010 (5) | −0.0075 (6) |
O1 | 0.0109 (5) | 0.0159 (6) | 0.0200 (6) | −0.0010 (4) | 0.0025 (4) | −0.0102 (5) |
C2 | 0.0108 (6) | 0.0111 (7) | 0.0150 (8) | −0.0022 (5) | 0.0020 (5) | −0.0064 (6) |
O2 | 0.0140 (5) | 0.0105 (6) | 0.0208 (6) | −0.0028 (4) | 0.0020 (4) | −0.0061 (5) |
C3 | 0.0123 (6) | 0.0140 (8) | 0.0101 (7) | −0.0019 (6) | 0.0021 (5) | −0.0042 (6) |
N3 | 0.0159 (6) | 0.0142 (7) | 0.0127 (7) | −0.0004 (5) | 0.0002 (5) | −0.0058 (6) |
O3A | 0.0190 (6) | 0.0237 (7) | 0.0175 (6) | −0.0095 (5) | 0.0049 (4) | −0.0075 (5) |
O3B | 0.0243 (6) | 0.0276 (7) | 0.0139 (6) | −0.0036 (5) | −0.0017 (5) | −0.0087 (5) |
O1W | 0.0141 (5) | 0.0158 (6) | 0.0144 (6) | −0.0002 (4) | 0.0013 (4) | −0.0064 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.4192 (17) | O2—H2H | 0.80 (2) |
C1—C3i | 1.530 (2) | C3—N3 | 1.5136 (19) |
C1—C2 | 1.532 (2) | C3—C1i | 1.530 (2) |
C1—H1A | 1.00 | C3—H3A | 1.00 |
O1—H1H | 0.87 (2) | N3—O3A | 1.2300 (17) |
C2—O2 | 1.4188 (18) | N3—O3B | 1.2303 (18) |
C2—C3 | 1.517 (2) | O1W—H1W | 0.83 (2) |
C2—H2A | 1.00 | O1W—H2W | 0.82 (2) |
| | | |
O1—C1—C3i | 107.68 (11) | C1—C2—H2A | 109.5 |
O1—C1—C2 | 111.37 (12) | C2—O2—H2H | 109.5 (15) |
C3i—C1—C2 | 109.11 (11) | N3—C3—C2 | 110.44 (12) |
O1—C1—H1A | 109.6 | N3—C3—C1i | 106.86 (11) |
C3i—C1—H1A | 109.6 | C2—C3—C1i | 112.84 (12) |
C2—C1—H1A | 109.6 | N3—C3—H3A | 108.9 |
C1—O1—H1H | 108.3 (14) | C2—C3—H3A | 108.9 |
O2—C2—C3 | 110.27 (12) | C1i—C3—H3A | 108.9 |
O2—C2—C1 | 108.29 (11) | O3A—N3—O3B | 123.73 (13) |
C3—C2—C1 | 109.83 (12) | O3A—N3—C3 | 119.12 (12) |
O2—C2—H2A | 109.5 | O3B—N3—C3 | 117.12 (12) |
C3—C2—H2A | 109.5 | H1W—O1W—H2W | 99.4 (19) |
| | | |
O1—C1—C2—O2 | 57.59 (15) | O2—C2—C3—C1i | −177.30 (11) |
C3i—C1—C2—O2 | 176.31 (11) | C1—C2—C3—C1i | −58.03 (15) |
O1—C1—C2—C3 | −62.89 (15) | C2—C3—N3—O3A | 21.12 (18) |
C3i—C1—C2—C3 | 55.83 (16) | C1i—C3—N3—O3A | −101.96 (15) |
O2—C2—C3—N3 | 63.18 (14) | C2—C3—N3—O3B | −160.94 (12) |
C1—C2—C3—N3 | −177.56 (11) | C1i—C3—N3—O3B | 75.98 (15) |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1H···O1W | 0.87 (2) | 1.89 (2) | 2.7549 (16) | 178 (2) |
O2—H2H···O1Wii | 0.80 (2) | 1.95 (2) | 2.7478 (16) | 175 (2) |
O1W—H1W···O2iii | 0.83 (2) | 1.93 (2) | 2.7450 (16) | 169 (2) |
O1W—H2W···O3Aiv | 0.82 (2) | 2.12 (2) | 2.9299 (17) | 168 (2) |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) x−1, y, z+1. |