2,3,5,6-Tetra­hydroxy-1,4-di­nitro­cyclo­hexane dihydrate

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.

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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.05P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

C1—O1	1.4192 (17)	O2—H2H	0.80 (2)
C1—C3^i	1.530 (2)	C3—N3	1.5136 (19)
C1—C2	1.532 (2)	C3—C1^i	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—C3^i	107.68 (11)	C1—C2—H2A	109.5
O1—C1—C2	111.37 (12)	C2—O2—H2H	109.5 (15)
C3^i—C1—C2	109.11 (11)	N3—C3—C2	110.44 (12)
O1—C1—H1A	109.6	N3—C3—C1^i	106.86 (11)
C3^i—C1—H1A	109.6	C2—C3—C1^i	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)	C1^i—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—C1^i	−177.30 (11)
C3^i—C1—C2—O2	176.31 (11)	C1—C2—C3—C1^i	−58.03 (15)
O1—C1—C2—C3	−62.89 (15)	C2—C3—N3—O3A	21.12 (18)
C3^i—C1—C2—C3	55.83 (16)	C1^i—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)	C1^i—C3—N3—O3B	75.98 (15)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

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···O1W^ii	0.80 (2)	1.95 (2)	2.7478 (16)	175 (2)
O1W—H1W···O2^iii	0.83 (2)	1.93 (2)	2.7450 (16)	169 (2)
O1W—H2W···O3A^iv	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.