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In the crystal structure of the title salt, C6H14N+·C6H2N3O7-, picrate anions lie parallel to one another with a relative orientation of nearly 120°. The protonated N atom of the cation makes one linear and two bifurcated hydrogen bonds with three neighbouring picrate ions. The centrosymmetrically related anions and cations form hydrogen-bonded graph-set motifs of R42(8) and R44(12) alternately along the [010] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031375/hg6239sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031375/hg6239Isup2.hkl
Contains datablock I

CCDC reference: 289763

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.176
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg. PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3 PLAT353_ALERT_3_B Long N-H Bond (0.87A) N4 - H4B ... 1.12 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - N3 .. 5.47 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O1 .. 2.74 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B .. O2 .. 2.71 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Cyclohexylammonium picrate top
Crystal data top
C6H14N+·C6H2N3O7F(000) = 1376
Mr = 328.29Dx = 1.458 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 23.543 (1) Åθ = 8–20°
b = 8.7177 (10) ŵ = 0.12 mm1
c = 18.6177 (14) ÅT = 293 K
β = 128.484 (10)°Needle, yellow
V = 2991.1 (4) Å30.25 × 0.20 × 0.15 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
1489 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 027
Absorption correction: ψ scan
(North et al., 1968)
k = 100
Tmin = 0.969, Tmax = 0.998l = 2217
2686 measured reflections2 standard reflections every 100 reflections
2619 independent reflections intensity decay: 1%
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)] = 0.062Hydrogen site location: difference Fourier map
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0687P)2 + 6.4872P]
where P = (Fo2 + 2Fc2)/3
2619 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.39 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
O10.01300 (14)0.1072 (3)0.11314 (16)0.0505 (7)
O20.08156 (18)0.1469 (3)0.2131 (2)0.0744 (9)
O30.0937 (2)0.1498 (4)0.3361 (2)0.1055 (14)
O40.19891 (17)0.3031 (4)0.52475 (19)0.0744 (10)
O50.1796 (2)0.5228 (4)0.4608 (2)0.0826 (11)
O60.0015 (3)0.5624 (4)0.1377 (2)0.1238 (18)
O70.0165 (2)0.3911 (4)0.0511 (2)0.1106 (15)
N10.08656 (18)0.0815 (4)0.2749 (2)0.0557 (9)
N20.17171 (18)0.3840 (4)0.4574 (2)0.0540 (9)
N30.01044 (18)0.4347 (4)0.1262 (2)0.0500 (8)
C10.04748 (17)0.1693 (4)0.1907 (2)0.0371 (8)
C20.08688 (18)0.0863 (4)0.2762 (2)0.0378 (8)
C30.12551 (18)0.1537 (4)0.3612 (2)0.0429 (9)
H30.14950.09370.41380.052*
C40.12836 (19)0.3119 (4)0.3674 (2)0.0430 (9)
C50.09054 (18)0.4020 (4)0.2894 (2)0.0422 (9)
H50.09160.50840.29410.051*
C60.05124 (18)0.3322 (4)0.2048 (2)0.0385 (8)
N40.04160 (18)0.1747 (4)0.0154 (2)0.0454 (8)
C70.12270 (18)0.1654 (4)0.0397 (2)0.0408 (9)
H70.13390.17180.00280.049*
C80.1499 (2)0.0125 (4)0.0887 (2)0.0473 (10)
H8A0.12700.07010.04410.057*
H8B0.13720.00120.12900.057*
C90.2319 (2)0.0027 (5)0.1445 (3)0.0594 (11)
H9A0.24400.00310.10330.071*
H9B0.24910.09290.17850.071*
C100.2696 (2)0.1365 (5)0.2111 (3)0.0609 (12)
H10A0.26150.13040.25610.073*
H10B0.32150.13020.24330.073*
C110.2412 (2)0.2883 (5)0.1607 (3)0.0572 (11)
H11A0.25310.29830.11960.069*
H11B0.26440.37170.20460.069*
C120.1593 (2)0.2992 (4)0.1059 (2)0.0495 (10)
H12B0.14740.29780.14730.059*
H12C0.14180.39490.07200.059*
H4A0.034 (2)0.172 (5)0.022 (3)0.073 (16)*
H4B0.020 (3)0.072 (6)0.061 (4)0.107 (17)*
H4C0.024 (2)0.263 (5)0.048 (3)0.063 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0602 (17)0.0483 (15)0.0336 (13)0.0040 (13)0.0245 (13)0.0008 (12)
O20.086 (2)0.0547 (19)0.0546 (18)0.0137 (17)0.0297 (17)0.0019 (15)
O30.187 (4)0.057 (2)0.073 (2)0.009 (2)0.081 (3)0.0128 (18)
O40.081 (2)0.090 (2)0.0383 (15)0.0088 (18)0.0302 (16)0.0015 (16)
O50.112 (3)0.063 (2)0.065 (2)0.020 (2)0.051 (2)0.0222 (17)
O60.193 (4)0.042 (2)0.065 (2)0.019 (2)0.045 (3)0.0119 (17)
O70.174 (4)0.081 (3)0.052 (2)0.055 (3)0.058 (2)0.0224 (19)
N10.058 (2)0.050 (2)0.0406 (18)0.0015 (17)0.0212 (17)0.0024 (17)
N20.051 (2)0.067 (3)0.0433 (19)0.0060 (18)0.0291 (17)0.0097 (19)
N30.057 (2)0.042 (2)0.0428 (19)0.0068 (16)0.0267 (17)0.0061 (16)
C10.0313 (19)0.046 (2)0.0326 (19)0.0013 (17)0.0191 (16)0.0025 (16)
C20.036 (2)0.039 (2)0.0381 (19)0.0029 (16)0.0232 (17)0.0046 (16)
C30.038 (2)0.054 (2)0.0343 (18)0.0007 (18)0.0211 (17)0.0058 (18)
C40.039 (2)0.054 (2)0.0357 (19)0.0055 (18)0.0235 (17)0.0059 (17)
C50.043 (2)0.043 (2)0.046 (2)0.0031 (17)0.0307 (19)0.0033 (17)
C60.038 (2)0.043 (2)0.0340 (18)0.0031 (17)0.0224 (16)0.0074 (16)
N40.049 (2)0.043 (2)0.0338 (18)0.0053 (17)0.0205 (16)0.0061 (16)
C70.045 (2)0.047 (2)0.0344 (18)0.0019 (18)0.0263 (17)0.0002 (17)
C80.052 (2)0.043 (2)0.045 (2)0.0034 (18)0.0293 (19)0.0001 (17)
C90.054 (3)0.058 (3)0.062 (3)0.010 (2)0.034 (2)0.002 (2)
C100.042 (2)0.071 (3)0.056 (2)0.003 (2)0.023 (2)0.004 (2)
C110.051 (3)0.059 (3)0.055 (2)0.010 (2)0.030 (2)0.005 (2)
C120.055 (3)0.045 (2)0.042 (2)0.0004 (19)0.0269 (19)0.0001 (18)
Geometric parameters (Å, º) top
O1—C11.256 (4)N4—H4B1.11 (6)
O2—N11.222 (4)N4—H4C0.91 (5)
O3—N11.203 (4)C7—C81.514 (5)
O4—N21.217 (4)C7—C121.515 (5)
O5—N21.220 (4)C7—H70.9800
O6—N31.200 (4)C8—C91.522 (5)
O7—N31.182 (4)C8—H8A0.9700
N1—C21.463 (5)C8—H8B0.9700
N2—C41.455 (5)C9—C101.522 (6)
N3—C61.454 (5)C9—H9A0.9700
C1—C61.438 (5)C9—H9B0.9700
C1—C21.442 (5)C10—C111.516 (6)
C2—C31.372 (5)C10—H10A0.9700
C3—C41.382 (5)C10—H10B0.9700
C3—H30.9300C11—C121.523 (5)
C4—C51.382 (5)C11—H11A0.9700
C5—C61.376 (5)C11—H11B0.9700
C5—H50.9300C12—H12B0.9700
N4—C71.505 (5)C12—H12C0.9700
N4—H4A0.82 (5)
O3—N1—O2122.4 (4)C8—C7—C12112.0 (3)
O3—N1—C2118.9 (4)N4—C7—H7108.1
O2—N1—C2118.7 (3)C8—C7—H7108.1
O4—N2—O5123.8 (4)C12—C7—H7108.1
O4—N2—C4118.6 (4)C7—C8—C9110.0 (3)
O5—N2—C4117.6 (4)C7—C8—H8A109.7
O7—N3—O6119.8 (4)C9—C8—H8A109.7
O7—N3—C6121.7 (3)C7—C8—H8B109.7
O6—N3—C6118.1 (3)C9—C8—H8B109.7
O1—C1—C6123.9 (3)H8A—C8—H8B108.2
O1—C1—C2124.4 (3)C8—C9—C10111.3 (3)
C6—C1—C2111.7 (3)C8—C9—H9A109.4
C3—C2—C1124.6 (3)C10—C9—H9A109.4
C3—C2—N1116.1 (3)C8—C9—H9B109.4
C1—C2—N1119.3 (3)C10—C9—H9B109.4
C2—C3—C4119.1 (3)H9A—C9—H9B108.0
C2—C3—H3120.4C11—C10—C9110.8 (3)
C4—C3—H3120.4C11—C10—H10A109.5
C5—C4—C3120.9 (3)C9—C10—H10A109.5
C5—C4—N2119.7 (4)C11—C10—H10B109.5
C3—C4—N2119.4 (3)C9—C10—H10B109.5
C6—C5—C4119.0 (4)H10A—C10—H10B108.1
C6—C5—H5120.5C10—C11—C12110.9 (3)
C4—C5—H5120.5C10—C11—H11A109.5
C5—C6—C1124.6 (3)C12—C11—H11A109.5
C5—C6—N3115.7 (3)C10—C11—H11B109.5
C1—C6—N3119.7 (3)C12—C11—H11B109.5
C7—N4—H4A106 (3)H11A—C11—H11B108.0
C7—N4—H4B105 (3)C7—C12—C11109.8 (3)
H4A—N4—H4B113 (4)C7—C12—H12B109.7
C7—N4—H4C111 (3)C11—C12—H12B109.7
H4A—N4—H4C110 (4)C7—C12—H12C109.7
H4B—N4—H4C112 (3)C11—C12—H12C109.7
N4—C7—C8109.8 (3)H12B—C12—H12C108.2
N4—C7—C12110.6 (3)
O1—C1—C2—C3179.0 (3)C4—C5—C6—C11.4 (5)
C6—C1—C2—C32.2 (5)C4—C5—C6—N3177.4 (3)
O1—C1—C2—N11.3 (5)O1—C1—C6—C5178.0 (3)
C6—C1—C2—N1177.6 (3)C2—C1—C6—C53.2 (5)
O3—N1—C2—C327.9 (6)O1—C1—C6—N33.3 (5)
O2—N1—C2—C3149.6 (3)C2—C1—C6—N3175.6 (3)
O3—N1—C2—C1151.9 (4)O7—N3—C6—C5168.7 (4)
O2—N1—C2—C130.6 (5)O6—N3—C6—C518.5 (6)
C1—C2—C3—C40.6 (6)O7—N3—C6—C112.5 (6)
N1—C2—C3—C4179.7 (3)O6—N3—C6—C1160.4 (4)
C2—C3—C4—C52.7 (6)N4—C7—C8—C9180.0 (3)
C2—C3—C4—N2177.4 (3)C12—C7—C8—C956.8 (4)
O4—N2—C4—C5173.1 (4)C7—C8—C9—C1055.6 (4)
O5—N2—C4—C58.1 (6)C8—C9—C10—C1156.2 (5)
O4—N2—C4—C36.8 (5)C9—C10—C11—C1256.7 (5)
O5—N2—C4—C3172.0 (4)N4—C7—C12—C11179.8 (3)
C3—C4—C5—C61.8 (5)C8—C7—C12—C1157.3 (4)
N2—C4—C5—C6178.4 (3)C10—C11—C12—C756.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O10.82 (5)2.12 (5)2.921 (5)166 (4)
N4—H4A···O70.82 (5)2.48 (5)3.011 (5)124 (4)
N4—H4B···O1i1.11 (6)1.75 (6)2.844 (4)168 (4)
N4—H4B···O2i1.11 (6)2.40 (5)2.955 (4)109 (3)
N4—H4C···O6ii0.91 (5)2.07 (5)2.942 (5)162 (4)
C8—H8A···O1i0.972.743.462 (5)131
C7—H7···O3iii0.982.533.410 (5)150
C10—H10B···O2iv0.972.713.417 (5)130
Symmetry codes: (i) x, y, z; (ii) x, y+1, z; (iii) x, y, z1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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