Cyclo­hexyl­ammonium picrate

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.

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

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Computing details

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

Crystal data

C6H14N^+·C6H2N3O7^−	F(000) = 1376
Mr = 328.29	Dx = 1.458 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 23.543 (1) Å	θ = 8–20°
b = 8.7177 (10) Å	µ = 0.12 mm^−1
c = 18.6177 (14) Å	T = 293 K
β = 128.484 (10)°	Needle, yellow
V = 2991.1 (4) Å^3	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	1489 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–2θ scans	h = 0→27
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.969, Tmax = 0.998	l = −22→17
2686 measured reflections	2 standard reflections every 100 reflections
2619 independent reflections	intensity decay: 1%

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)] = 0.062	Hydrogen site location: difference Fourier map
wR(F^2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0687P)^2 + 6.4872P] where P = (Fo^2 + 2Fc^2)/3
2619 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.39 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
O1	0.01300 (14)	0.1072 (3)	0.11314 (16)	0.0505 (7)
O2	0.08156 (18)	−0.1469 (3)	0.2131 (2)	0.0744 (9)
O3	0.0937 (2)	−0.1498 (4)	0.3361 (2)	0.1055 (14)
O4	0.19891 (17)	0.3031 (4)	0.52475 (19)	0.0744 (10)
O5	0.1796 (2)	0.5228 (4)	0.4608 (2)	0.0826 (11)
O6	−0.0015 (3)	0.5624 (4)	0.1377 (2)	0.1238 (18)
O7	−0.0165 (2)	0.3911 (4)	0.0511 (2)	0.1106 (15)
N1	0.08656 (18)	−0.0815 (4)	0.2749 (2)	0.0557 (9)
N2	0.17171 (18)	0.3840 (4)	0.4574 (2)	0.0540 (9)
N3	0.01044 (18)	0.4347 (4)	0.1262 (2)	0.0500 (8)
C1	0.04748 (17)	0.1693 (4)	0.1907 (2)	0.0371 (8)
C2	0.08688 (18)	0.0863 (4)	0.2762 (2)	0.0378 (8)
C3	0.12551 (18)	0.1537 (4)	0.3612 (2)	0.0429 (9)
H3	0.1495	0.0937	0.4138	0.052*
C4	0.12836 (19)	0.3119 (4)	0.3674 (2)	0.0430 (9)
C5	0.09054 (18)	0.4020 (4)	0.2894 (2)	0.0422 (9)
H5	0.0916	0.5084	0.2941	0.051*
C6	0.05124 (18)	0.3322 (4)	0.2048 (2)	0.0385 (8)
N4	0.04160 (18)	0.1747 (4)	−0.0154 (2)	0.0454 (8)
C7	0.12270 (18)	0.1654 (4)	0.0397 (2)	0.0408 (9)
H7	0.1339	0.1718	−0.0028	0.049*
C8	0.1499 (2)	0.0125 (4)	0.0887 (2)	0.0473 (10)
H8A	0.1270	−0.0701	0.0441	0.057*
H8B	0.1372	0.0012	0.1290	0.057*
C9	0.2319 (2)	0.0027 (5)	0.1445 (3)	0.0594 (11)
H9A	0.2440	0.0031	0.1033	0.071*
H9B	0.2491	−0.0929	0.1785	0.071*
C10	0.2696 (2)	0.1365 (5)	0.2111 (3)	0.0609 (12)
H10A	0.2615	0.1304	0.2561	0.073*
H10B	0.3215	0.1302	0.2433	0.073*
C11	0.2412 (2)	0.2883 (5)	0.1607 (3)	0.0572 (11)
H11A	0.2531	0.2983	0.1196	0.069*
H11B	0.2644	0.3717	0.2046	0.069*
C12	0.1593 (2)	0.2992 (4)	0.1059 (2)	0.0495 (10)
H12B	0.1474	0.2978	0.1473	0.059*
H12C	0.1418	0.3949	0.0720	0.059*
H4A	0.034 (2)	0.172 (5)	0.022 (3)	0.073 (16)*
H4B	0.020 (3)	0.072 (6)	−0.061 (4)	0.107 (17)*
H4C	0.024 (2)	0.263 (5)	−0.048 (3)	0.063 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0602 (17)	0.0483 (15)	0.0336 (13)	−0.0040 (13)	0.0245 (13)	0.0008 (12)
O2	0.086 (2)	0.0547 (19)	0.0546 (18)	0.0137 (17)	0.0297 (17)	−0.0019 (15)
O3	0.187 (4)	0.057 (2)	0.073 (2)	−0.009 (2)	0.081 (3)	0.0128 (18)
O4	0.081 (2)	0.090 (2)	0.0383 (15)	−0.0088 (18)	0.0302 (16)	−0.0015 (16)
O5	0.112 (3)	0.063 (2)	0.065 (2)	−0.020 (2)	0.051 (2)	−0.0222 (17)
O6	0.193 (4)	0.042 (2)	0.065 (2)	0.019 (2)	0.045 (3)	0.0119 (17)
O7	0.174 (4)	0.081 (3)	0.052 (2)	0.055 (3)	0.058 (2)	0.0224 (19)
N1	0.058 (2)	0.050 (2)	0.0406 (18)	0.0015 (17)	0.0212 (17)	0.0024 (17)
N2	0.051 (2)	0.067 (3)	0.0433 (19)	−0.0060 (18)	0.0291 (17)	−0.0097 (19)
N3	0.057 (2)	0.042 (2)	0.0428 (19)	0.0068 (16)	0.0267 (17)	0.0061 (16)
C1	0.0313 (19)	0.046 (2)	0.0326 (19)	0.0013 (17)	0.0191 (16)	0.0025 (16)
C2	0.036 (2)	0.039 (2)	0.0381 (19)	0.0029 (16)	0.0232 (17)	0.0046 (16)
C3	0.038 (2)	0.054 (2)	0.0343 (18)	0.0007 (18)	0.0211 (17)	0.0058 (18)
C4	0.039 (2)	0.054 (2)	0.0357 (19)	−0.0055 (18)	0.0235 (17)	−0.0059 (17)
C5	0.043 (2)	0.043 (2)	0.046 (2)	−0.0031 (17)	0.0307 (19)	−0.0033 (17)
C6	0.038 (2)	0.043 (2)	0.0340 (18)	0.0031 (17)	0.0224 (16)	0.0074 (16)
N4	0.049 (2)	0.043 (2)	0.0338 (18)	0.0053 (17)	0.0205 (16)	0.0061 (16)
C7	0.045 (2)	0.047 (2)	0.0344 (18)	0.0019 (18)	0.0263 (17)	−0.0002 (17)
C8	0.052 (2)	0.043 (2)	0.045 (2)	0.0034 (18)	0.0293 (19)	0.0001 (17)
C9	0.054 (3)	0.058 (3)	0.062 (3)	0.010 (2)	0.034 (2)	0.002 (2)
C10	0.042 (2)	0.071 (3)	0.056 (2)	0.003 (2)	0.023 (2)	0.004 (2)
C11	0.051 (3)	0.059 (3)	0.055 (2)	−0.010 (2)	0.030 (2)	−0.005 (2)
C12	0.055 (3)	0.045 (2)	0.042 (2)	0.0004 (19)	0.0269 (19)	0.0001 (18)

Geometric parameters (Å, º)

O1—C1	1.256 (4)	N4—H4B	1.11 (6)
O2—N1	1.222 (4)	N4—H4C	0.91 (5)
O3—N1	1.203 (4)	C7—C8	1.514 (5)
O4—N2	1.217 (4)	C7—C12	1.515 (5)
O5—N2	1.220 (4)	C7—H7	0.9800
O6—N3	1.200 (4)	C8—C9	1.522 (5)
O7—N3	1.182 (4)	C8—H8A	0.9700
N1—C2	1.463 (5)	C8—H8B	0.9700
N2—C4	1.455 (5)	C9—C10	1.522 (6)
N3—C6	1.454 (5)	C9—H9A	0.9700
C1—C6	1.438 (5)	C9—H9B	0.9700
C1—C2	1.442 (5)	C10—C11	1.516 (6)
C2—C3	1.372 (5)	C10—H10A	0.9700
C3—C4	1.382 (5)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.523 (5)
C4—C5	1.382 (5)	C11—H11A	0.9700
C5—C6	1.376 (5)	C11—H11B	0.9700
C5—H5	0.9300	C12—H12B	0.9700
N4—C7	1.505 (5)	C12—H12C	0.9700
N4—H4A	0.82 (5)
O3—N1—O2	122.4 (4)	C8—C7—C12	112.0 (3)
O3—N1—C2	118.9 (4)	N4—C7—H7	108.1
O2—N1—C2	118.7 (3)	C8—C7—H7	108.1
O4—N2—O5	123.8 (4)	C12—C7—H7	108.1
O4—N2—C4	118.6 (4)	C7—C8—C9	110.0 (3)
O5—N2—C4	117.6 (4)	C7—C8—H8A	109.7
O7—N3—O6	119.8 (4)	C9—C8—H8A	109.7
O7—N3—C6	121.7 (3)	C7—C8—H8B	109.7
O6—N3—C6	118.1 (3)	C9—C8—H8B	109.7
O1—C1—C6	123.9 (3)	H8A—C8—H8B	108.2
O1—C1—C2	124.4 (3)	C8—C9—C10	111.3 (3)
C6—C1—C2	111.7 (3)	C8—C9—H9A	109.4
C3—C2—C1	124.6 (3)	C10—C9—H9A	109.4
C3—C2—N1	116.1 (3)	C8—C9—H9B	109.4
C1—C2—N1	119.3 (3)	C10—C9—H9B	109.4
C2—C3—C4	119.1 (3)	H9A—C9—H9B	108.0
C2—C3—H3	120.4	C11—C10—C9	110.8 (3)
C4—C3—H3	120.4	C11—C10—H10A	109.5
C5—C4—C3	120.9 (3)	C9—C10—H10A	109.5
C5—C4—N2	119.7 (4)	C11—C10—H10B	109.5
C3—C4—N2	119.4 (3)	C9—C10—H10B	109.5
C6—C5—C4	119.0 (4)	H10A—C10—H10B	108.1
C6—C5—H5	120.5	C10—C11—C12	110.9 (3)
C4—C5—H5	120.5	C10—C11—H11A	109.5
C5—C6—C1	124.6 (3)	C12—C11—H11A	109.5
C5—C6—N3	115.7 (3)	C10—C11—H11B	109.5
C1—C6—N3	119.7 (3)	C12—C11—H11B	109.5
C7—N4—H4A	106 (3)	H11A—C11—H11B	108.0
C7—N4—H4B	105 (3)	C7—C12—C11	109.8 (3)
H4A—N4—H4B	113 (4)	C7—C12—H12B	109.7
C7—N4—H4C	111 (3)	C11—C12—H12B	109.7
H4A—N4—H4C	110 (4)	C7—C12—H12C	109.7
H4B—N4—H4C	112 (3)	C11—C12—H12C	109.7
N4—C7—C8	109.8 (3)	H12B—C12—H12C	108.2
N4—C7—C12	110.6 (3)
O1—C1—C2—C3	179.0 (3)	C4—C5—C6—C1	−1.4 (5)
C6—C1—C2—C3	−2.2 (5)	C4—C5—C6—N3	177.4 (3)
O1—C1—C2—N1	−1.3 (5)	O1—C1—C6—C5	−178.0 (3)
C6—C1—C2—N1	177.6 (3)	C2—C1—C6—C5	3.2 (5)
O3—N1—C2—C3	27.9 (6)	O1—C1—C6—N3	3.3 (5)
O2—N1—C2—C3	−149.6 (3)	C2—C1—C6—N3	−175.6 (3)
O3—N1—C2—C1	−151.9 (4)	O7—N3—C6—C5	168.7 (4)
O2—N1—C2—C1	30.6 (5)	O6—N3—C6—C5	−18.5 (6)
C1—C2—C3—C4	−0.6 (6)	O7—N3—C6—C1	−12.5 (6)
N1—C2—C3—C4	179.7 (3)	O6—N3—C6—C1	160.4 (4)
C2—C3—C4—C5	2.7 (6)	N4—C7—C8—C9	180.0 (3)
C2—C3—C4—N2	−177.4 (3)	C12—C7—C8—C9	−56.8 (4)
O4—N2—C4—C5	173.1 (4)	C7—C8—C9—C10	55.6 (4)
O5—N2—C4—C5	−8.1 (6)	C8—C9—C10—C11	−56.2 (5)
O4—N2—C4—C3	−6.8 (5)	C9—C10—C11—C12	56.7 (5)
O5—N2—C4—C3	172.0 (4)	N4—C7—C12—C11	−179.8 (3)
C3—C4—C5—C6	−1.8 (5)	C8—C7—C12—C11	57.3 (4)
N2—C4—C5—C6	178.4 (3)	C10—C11—C12—C7	−56.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1	0.82 (5)	2.12 (5)	2.921 (5)	166 (4)
N4—H4A···O7	0.82 (5)	2.48 (5)	3.011 (5)	124 (4)
N4—H4B···O1^i	1.11 (6)	1.75 (6)	2.844 (4)	168 (4)
N4—H4B···O2^i	1.11 (6)	2.40 (5)	2.955 (4)	109 (3)
N4—H4C···O6^ii	0.91 (5)	2.07 (5)	2.942 (5)	162 (4)
C8—H8A···O1^i	0.97	2.74	3.462 (5)	131
C7—H7···O3^iii	0.98	2.53	3.410 (5)	150
C10—H10B···O2^iv	0.97	2.71	3.417 (5)	130

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) x, −y, z−1/2; (iv) −x+1/2, y+1/2, −z+1/2.