Hexane-1,6-di­ammonium dipicrate dihydrate

The title salt, C₆H₁₈N₂²⁺·2C₆H₂N₃O₇⁻·2H₂O, consists of one hexane-1,6-di­ammonium cation, two picrate anions and two water mol­ecules of crystallization. The cation lies across a centre of symmetry. The O atoms of the water mol­ecules, and the phenolate group and nitro groups of the picrate anions act as acceptors to form N—H...O and O—H...O hydrogen bonds. In the crystal structure, this leads to the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.120
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

hexane-1,6-diammonium dipicrate dihydrate

Crystal data

C6H18N2^2+·2C6H2N3O7^−·2H2O	Z = 1
Mr = 610.47	F(000) = 318
Triclinic, P1	Dx = 1.589 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.165 (1) Å	Cell parameters from 900 reflections
b = 8.215 (2) Å	θ = 2.3–27.5°
c = 11.316 (2) Å	µ = 0.14 mm^−1
α = 101.36 (3)°	T = 293 K
β = 101.31 (3)°	Block, yellow
γ = 92.57 (3)°	0.48 × 0.38 × 0.30 mm
V = 637.9 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2229 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 0 pixels mm^-1	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→9
Tmin = 0.923, Tmax = 0.956	l = −13→12
3381 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 0.3169P] where P = (Fo^2 + 2Fc^2)/3
2229 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.21 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
O1W	0.3206 (3)	0.1058 (2)	0.46059 (18)	0.0608 (5)
O2	0.3115 (2)	−0.04242 (18)	1.20531 (12)	0.0521 (4)
O3	0.2807 (3)	−0.3625 (2)	1.07563 (15)	0.0716 (6)
O4	0.0878 (3)	−0.40669 (19)	0.90115 (15)	0.0675 (5)
O5	0.2836 (3)	0.3004 (2)	1.26559 (15)	0.0677 (5)
O6	0.5028 (3)	0.3857 (2)	1.18235 (15)	0.0630 (5)
O7	0.1191 (3)	−0.0084 (2)	0.64820 (13)	0.0589 (5)
O8	0.2343 (2)	0.24419 (19)	0.73023 (13)	0.0514 (4)
C3	0.0696 (3)	0.5675 (2)	0.54457 (18)	0.0414 (5)
H3A	0.1050	0.5335	0.6228	0.062*
H3B	0.0058	0.6690	0.5589	0.062*
N2	0.3689 (3)	0.2876 (2)	1.18202 (15)	0.0440 (4)
N3	0.1914 (3)	−0.3132 (2)	0.98843 (15)	0.0421 (4)
N4	0.1890 (2)	0.1021 (2)	0.73870 (15)	0.0395 (4)
C1	0.2504 (3)	0.6043 (3)	0.49928 (18)	0.0398 (5)
H1D	0.3377	0.6824	0.5642	0.048*
H1F	0.3121	0.5021	0.4823	0.048*
C2	0.2130 (3)	0.6760 (2)	0.38472 (18)	0.0386 (5)
H2A	0.1286	0.5971	0.3187	0.046*
H2B	0.1495	0.7774	0.4008	0.046*
N1	0.3936 (2)	0.7137 (2)	0.34524 (14)	0.0392 (4)
H1A	0.3673	0.7556	0.2777	0.059*
H1B	0.4511	0.6204	0.3293	0.059*
H1E	0.4704	0.7875	0.4052	0.059*
C4	0.2178 (3)	−0.1368 (2)	0.98550 (16)	0.0334 (4)
C5	0.2811 (3)	−0.0142 (2)	1.09905 (16)	0.0344 (4)
C6	0.3075 (3)	0.1505 (2)	1.07521 (16)	0.0346 (4)
C7	0.2826 (3)	0.1901 (2)	0.96242 (17)	0.0348 (4)
H7A	0.3085	0.2989	0.9544	0.042*
C8	0.2174 (3)	0.0635 (2)	0.85968 (16)	0.0331 (4)
C9	0.1833 (3)	−0.0992 (2)	0.87080 (17)	0.0347 (4)
H9A	0.1372	−0.1825	0.8010	0.042*
H1G	0.302 (4)	0.099 (4)	0.388 (3)	0.081 (10)*
H1H	0.221 (6)	0.077 (5)	0.482 (4)	0.124 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.0552 (11)	0.0827 (13)	0.0378 (10)	−0.0114 (9)	0.0048 (8)	0.0057 (8)
O2	0.0823 (12)	0.0440 (8)	0.0294 (8)	0.0090 (7)	0.0080 (7)	0.0096 (6)
O3	0.1092 (15)	0.0434 (9)	0.0527 (10)	0.0006 (9)	−0.0113 (10)	0.0173 (8)
O4	0.0925 (14)	0.0420 (9)	0.0533 (10)	−0.0191 (9)	−0.0086 (9)	0.0046 (7)
O5	0.1024 (15)	0.0568 (10)	0.0415 (9)	0.0086 (9)	0.0247 (10)	−0.0053 (7)
O6	0.0699 (11)	0.0454 (9)	0.0601 (11)	−0.0122 (8)	−0.0010 (8)	−0.0027 (7)
O7	0.0811 (12)	0.0585 (10)	0.0294 (8)	−0.0106 (8)	0.0015 (7)	0.0045 (7)
O8	0.0631 (10)	0.0485 (9)	0.0461 (9)	−0.0002 (7)	0.0107 (7)	0.0199 (7)
C3	0.0452 (12)	0.0414 (11)	0.0352 (10)	−0.0044 (9)	0.0103 (9)	0.0025 (8)
N2	0.0553 (11)	0.0354 (9)	0.0351 (9)	0.0073 (8)	−0.0012 (8)	0.0029 (7)
N3	0.0510 (10)	0.0355 (9)	0.0376 (9)	−0.0029 (8)	0.0054 (8)	0.0076 (7)
N4	0.0401 (9)	0.0456 (10)	0.0335 (9)	0.0024 (7)	0.0068 (7)	0.0111 (7)
C1	0.0379 (11)	0.0446 (11)	0.0348 (10)	−0.0032 (8)	0.0037 (8)	0.0089 (8)
C2	0.0351 (10)	0.0382 (10)	0.0421 (11)	−0.0003 (8)	0.0057 (8)	0.0109 (8)
N1	0.0415 (9)	0.0408 (9)	0.0347 (9)	−0.0026 (7)	0.0047 (7)	0.0110 (7)
C4	0.0338 (10)	0.0314 (10)	0.0335 (10)	0.0005 (7)	0.0048 (8)	0.0063 (8)
C5	0.0366 (10)	0.0370 (10)	0.0295 (10)	0.0047 (8)	0.0069 (8)	0.0064 (8)
C6	0.0371 (10)	0.0337 (10)	0.0294 (10)	0.0031 (8)	0.0034 (8)	0.0011 (8)
C7	0.0346 (10)	0.0325 (10)	0.0374 (10)	0.0021 (8)	0.0066 (8)	0.0082 (8)
C8	0.0321 (10)	0.0384 (10)	0.0289 (9)	0.0022 (8)	0.0060 (7)	0.0082 (8)
C9	0.0342 (10)	0.0370 (10)	0.0298 (9)	−0.0001 (8)	0.0046 (8)	0.0020 (8)

Geometric parameters (Å, º)

O1W—H1G	0.79 (3)	C1—H1D	0.9700
O1W—H1H	0.84 (4)	C1—H1F	0.9700
O2—C5	1.248 (2)	C2—N1	1.488 (3)
O3—N3	1.217 (2)	C2—H2A	0.9700
O4—N3	1.216 (2)	C2—H2B	0.9700
O5—N2	1.214 (2)	N1—H1A	0.8900
O6—N2	1.224 (2)	N1—H1B	0.8900
O7—N4	1.231 (2)	N1—H1E	0.8900
O8—N4	1.224 (2)	C4—C9	1.371 (3)
C3—C3^i	1.519 (4)	C4—C5	1.446 (3)
C3—C1	1.523 (3)	C5—C6	1.443 (3)
C3—H3A	0.9700	C6—C7	1.359 (3)
C3—H3B	0.9700	C7—C8	1.385 (3)
N2—C6	1.460 (2)	C7—H7A	0.9300
N3—C4	1.461 (2)	C8—C9	1.382 (3)
N4—C8	1.443 (2)	C9—H9A	0.9300
C1—C2	1.509 (3)
H1G—O1W—H1H	111 (3)	C1—C2—H2B	109.3
C3^i—C3—C1	113.7 (2)	H2A—C2—H2B	108.0
C3^i—C3—H3A	108.8	C2—N1—H1A	109.5
C1—C3—H3A	108.8	C2—N1—H1B	109.5
C3^i—C3—H3B	108.8	H1A—N1—H1B	109.5
C1—C3—H3B	108.8	C2—N1—H1E	109.5
H3A—C3—H3B	107.7	H1A—N1—H1E	109.5
O5—N2—O6	122.98 (18)	H1B—N1—H1E	109.5
O5—N2—C6	118.63 (18)	C9—C4—C5	123.91 (16)
O6—N2—C6	118.38 (18)	C9—C4—N3	115.96 (16)
O4—N3—O3	122.38 (17)	C5—C4—N3	120.11 (16)
O4—N3—C4	118.84 (17)	O2—C5—C6	122.73 (17)
O3—N3—C4	118.70 (16)	O2—C5—C4	126.09 (17)
O8—N4—O7	122.54 (17)	C6—C5—C4	111.17 (16)
O8—N4—C8	118.56 (16)	C7—C6—C5	126.07 (17)
O7—N4—C8	118.89 (16)	C7—C6—N2	116.80 (16)
C2—C1—C3	113.17 (17)	C5—C6—N2	117.13 (16)
C2—C1—H1D	108.9	C6—C7—C8	117.99 (17)
C3—C1—H1D	108.9	C6—C7—H7A	121.0
C2—C1—H1F	108.9	C8—C7—H7A	121.0
C3—C1—H1F	108.9	C9—C8—C7	121.27 (17)
H1D—C1—H1F	107.8	C9—C8—N4	119.54 (16)
N1—C2—C1	111.43 (16)	C7—C8—N4	119.18 (16)
N1—C2—H2A	109.3	C4—C9—C8	119.49 (17)
C1—C2—H2A	109.3	C4—C9—H9A	120.3
N1—C2—H2B	109.3	C8—C9—H9A	120.3

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^ii	0.89	2.01	2.803 (2)	147
N1—H1A···O3^ii	0.89	2.25	2.931 (2)	133
N1—H1B···O6^iii	0.89	2.38	3.173 (3)	149
N1—H1E···O1W^iv	0.89	1.95	2.811 (3)	164
O1W—H1G···O2^iii	0.79 (3)	2.18 (3)	2.892 (2)	150 (3)
O1W—H1G···O5^iii	0.79 (3)	2.35 (3)	2.948 (3)	133 (3)
O1W—H1H···O7^v	0.84 (4)	2.56 (4)	3.153 (3)	129 (3)
O1W—H1H···O7	0.84 (4)	2.36 (4)	3.056 (3)	141 (3)

Symmetry codes: (ii) x, y+1, z−1; (iii) x, y, z−1; (iv) −x+1, −y+1, −z+1; (v) −x, −y, −z+1.