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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023918/su6142sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023918/su6142Isup2.hkl
Contains datablock I

CCDC reference: 253037

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

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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 top
Crystal data top
C6H18N22+·2C6H2N3O7·2H2OZ = 1
Mr = 610.47F(000) = 318
Triclinic, P1Dx = 1.589 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.165 (1) ÅCell parameters from 900 reflections
b = 8.215 (2) Åθ = 2.3–27.5°
c = 11.316 (2) ŵ = 0.14 mm1
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) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2229 independent reflections
Radiation source: fine-focus sealed tube1771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 1.9°
φ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 89
Tmin = 0.923, Tmax = 0.956l = 1312
3381 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0715P)2 + 0.3169P]
where P = (Fo2 + 2Fc2)/3
2229 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.21 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
O1W0.3206 (3)0.1058 (2)0.46059 (18)0.0608 (5)
O20.3115 (2)0.04242 (18)1.20531 (12)0.0521 (4)
O30.2807 (3)0.3625 (2)1.07563 (15)0.0716 (6)
O40.0878 (3)0.40669 (19)0.90115 (15)0.0675 (5)
O50.2836 (3)0.3004 (2)1.26559 (15)0.0677 (5)
O60.5028 (3)0.3857 (2)1.18235 (15)0.0630 (5)
O70.1191 (3)0.0084 (2)0.64820 (13)0.0589 (5)
O80.2343 (2)0.24419 (19)0.73023 (13)0.0514 (4)
C30.0696 (3)0.5675 (2)0.54457 (18)0.0414 (5)
H3A0.10500.53350.62280.062*
H3B0.00580.66900.55890.062*
N20.3689 (3)0.2876 (2)1.18202 (15)0.0440 (4)
N30.1914 (3)0.3132 (2)0.98843 (15)0.0421 (4)
N40.1890 (2)0.1021 (2)0.73870 (15)0.0395 (4)
C10.2504 (3)0.6043 (3)0.49928 (18)0.0398 (5)
H1D0.33770.68240.56420.048*
H1F0.31210.50210.48230.048*
C20.2130 (3)0.6760 (2)0.38472 (18)0.0386 (5)
H2A0.12860.59710.31870.046*
H2B0.14950.77740.40080.046*
N10.3936 (2)0.7137 (2)0.34524 (14)0.0392 (4)
H1A0.36730.75560.27770.059*
H1B0.45110.62040.32930.059*
H1E0.47040.78750.40520.059*
C40.2178 (3)0.1368 (2)0.98550 (16)0.0334 (4)
C50.2811 (3)0.0142 (2)1.09905 (16)0.0344 (4)
C60.3075 (3)0.1505 (2)1.07521 (16)0.0346 (4)
C70.2826 (3)0.1901 (2)0.96242 (17)0.0348 (4)
H7A0.30850.29890.95440.042*
C80.2174 (3)0.0635 (2)0.85968 (16)0.0331 (4)
C90.1833 (3)0.0992 (2)0.87080 (17)0.0347 (4)
H9A0.13720.18250.80100.042*
H1G0.302 (4)0.099 (4)0.388 (3)0.081 (10)*
H1H0.221 (6)0.077 (5)0.482 (4)0.124 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0552 (11)0.0827 (13)0.0378 (10)0.0114 (9)0.0048 (8)0.0057 (8)
O20.0823 (12)0.0440 (8)0.0294 (8)0.0090 (7)0.0080 (7)0.0096 (6)
O30.1092 (15)0.0434 (9)0.0527 (10)0.0006 (9)0.0113 (10)0.0173 (8)
O40.0925 (14)0.0420 (9)0.0533 (10)0.0191 (9)0.0086 (9)0.0046 (7)
O50.1024 (15)0.0568 (10)0.0415 (9)0.0086 (9)0.0247 (10)0.0053 (7)
O60.0699 (11)0.0454 (9)0.0601 (11)0.0122 (8)0.0010 (8)0.0027 (7)
O70.0811 (12)0.0585 (10)0.0294 (8)0.0106 (8)0.0015 (7)0.0045 (7)
O80.0631 (10)0.0485 (9)0.0461 (9)0.0002 (7)0.0107 (7)0.0199 (7)
C30.0452 (12)0.0414 (11)0.0352 (10)0.0044 (9)0.0103 (9)0.0025 (8)
N20.0553 (11)0.0354 (9)0.0351 (9)0.0073 (8)0.0012 (8)0.0029 (7)
N30.0510 (10)0.0355 (9)0.0376 (9)0.0029 (8)0.0054 (8)0.0076 (7)
N40.0401 (9)0.0456 (10)0.0335 (9)0.0024 (7)0.0068 (7)0.0111 (7)
C10.0379 (11)0.0446 (11)0.0348 (10)0.0032 (8)0.0037 (8)0.0089 (8)
C20.0351 (10)0.0382 (10)0.0421 (11)0.0003 (8)0.0057 (8)0.0109 (8)
N10.0415 (9)0.0408 (9)0.0347 (9)0.0026 (7)0.0047 (7)0.0110 (7)
C40.0338 (10)0.0314 (10)0.0335 (10)0.0005 (7)0.0048 (8)0.0063 (8)
C50.0366 (10)0.0370 (10)0.0295 (10)0.0047 (8)0.0069 (8)0.0064 (8)
C60.0371 (10)0.0337 (10)0.0294 (10)0.0031 (8)0.0034 (8)0.0011 (8)
C70.0346 (10)0.0325 (10)0.0374 (10)0.0021 (8)0.0066 (8)0.0082 (8)
C80.0321 (10)0.0384 (10)0.0289 (9)0.0022 (8)0.0060 (7)0.0082 (8)
C90.0342 (10)0.0370 (10)0.0298 (9)0.0001 (8)0.0046 (8)0.0020 (8)
Geometric parameters (Å, º) top
O1W—H1G0.79 (3)C1—H1D0.9700
O1W—H1H0.84 (4)C1—H1F0.9700
O2—C51.248 (2)C2—N11.488 (3)
O3—N31.217 (2)C2—H2A0.9700
O4—N31.216 (2)C2—H2B0.9700
O5—N21.214 (2)N1—H1A0.8900
O6—N21.224 (2)N1—H1B0.8900
O7—N41.231 (2)N1—H1E0.8900
O8—N41.224 (2)C4—C91.371 (3)
C3—C3i1.519 (4)C4—C51.446 (3)
C3—C11.523 (3)C5—C61.443 (3)
C3—H3A0.9700C6—C71.359 (3)
C3—H3B0.9700C7—C81.385 (3)
N2—C61.460 (2)C7—H7A0.9300
N3—C41.461 (2)C8—C91.382 (3)
N4—C81.443 (2)C9—H9A0.9300
C1—C21.509 (3)
H1G—O1W—H1H111 (3)C1—C2—H2B109.3
C3i—C3—C1113.7 (2)H2A—C2—H2B108.0
C3i—C3—H3A108.8C2—N1—H1A109.5
C1—C3—H3A108.8C2—N1—H1B109.5
C3i—C3—H3B108.8H1A—N1—H1B109.5
C1—C3—H3B108.8C2—N1—H1E109.5
H3A—C3—H3B107.7H1A—N1—H1E109.5
O5—N2—O6122.98 (18)H1B—N1—H1E109.5
O5—N2—C6118.63 (18)C9—C4—C5123.91 (16)
O6—N2—C6118.38 (18)C9—C4—N3115.96 (16)
O4—N3—O3122.38 (17)C5—C4—N3120.11 (16)
O4—N3—C4118.84 (17)O2—C5—C6122.73 (17)
O3—N3—C4118.70 (16)O2—C5—C4126.09 (17)
O8—N4—O7122.54 (17)C6—C5—C4111.17 (16)
O8—N4—C8118.56 (16)C7—C6—C5126.07 (17)
O7—N4—C8118.89 (16)C7—C6—N2116.80 (16)
C2—C1—C3113.17 (17)C5—C6—N2117.13 (16)
C2—C1—H1D108.9C6—C7—C8117.99 (17)
C3—C1—H1D108.9C6—C7—H7A121.0
C2—C1—H1F108.9C8—C7—H7A121.0
C3—C1—H1F108.9C9—C8—C7121.27 (17)
H1D—C1—H1F107.8C9—C8—N4119.54 (16)
N1—C2—C1111.43 (16)C7—C8—N4119.18 (16)
N1—C2—H2A109.3C4—C9—C8119.49 (17)
C1—C2—H2A109.3C4—C9—H9A120.3
N1—C2—H2B109.3C8—C9—H9A120.3
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2ii0.892.012.803 (2)147
N1—H1A···O3ii0.892.252.931 (2)133
N1—H1B···O6iii0.892.383.173 (3)149
N1—H1E···O1Wiv0.891.952.811 (3)164
O1W—H1G···O2iii0.79 (3)2.18 (3)2.892 (2)150 (3)
O1W—H1G···O5iii0.79 (3)2.35 (3)2.948 (3)133 (3)
O1W—H1H···O7v0.84 (4)2.56 (4)3.153 (3)129 (3)
O1W—H1H···O70.84 (4)2.36 (4)3.056 (3)141 (3)
Symmetry codes: (ii) x, y+1, z1; (iii) x, y, z1; (iv) x+1, y+1, z+1; (v) x, y, z+1.
 

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