Piperidinium picrate

In the title compound, C₅H₁₂N⁺·C₆H₂N₃O₇⁻, the protonated N atom of the cation makes one linear and two bifucated hydrogen bonds with two neighbouring picrate anions. Centrosymmetrically related anions and cations form a hydrogen-bonded network with a graph-set motif R₄⁴(12). The picrate ions are parallel to one another and governed by π–π inter­actions; they form columns along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.121
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.96 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 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.

Piperidinium picrate

Crystal data

C5H12N^+·C6H2N3O7^−	Z = 2
Mr = 314.26	F(000) = 328
Triclinic, P1	Dx = 1.533 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8750 (15) Å	Cell parameters from 25 reflections
b = 9.3471 (17) Å	θ = 8–15°
c = 11.9198 (11) Å	µ = 0.13 mm^−1
α = 105.393 (12)°	T = 293 K
β = 91.856 (11)°	Prism, yellow
γ = 111.341 (18)°	0.54 × 0.52 × 0.38 mm
V = 680.7 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1830 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω–2θ scans	h = −2→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→10
Tmin = 0.873, Tmax = 0.961	l = −14→14
2606 measured reflections	2 standard reflections every 100 reflections
2382 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 0.2412P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2382 reflections	Δρmax = 0.43 e Å^−3
208 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (4)

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	0.2397 (3)	0.94396 (16)	0.22563 (12)	0.0587 (4)
O2	0.1961 (3)	0.67125 (18)	0.05737 (15)	0.0703 (5)
O3	0.1002 (3)	0.65672 (18)	−0.11915 (14)	0.0780 (6)
O4	0.2936 (3)	1.1182 (2)	−0.24481 (13)	0.0730 (5)
O5	0.3397 (3)	1.34806 (19)	−0.12344 (15)	0.0763 (5)
O6	0.5341 (3)	1.39507 (19)	0.30131 (14)	0.0740 (5)
O7	0.2416 (3)	1.2472 (2)	0.34014 (15)	0.0836 (6)
N1	0.1657 (3)	0.73365 (18)	−0.01645 (15)	0.0460 (4)
N2	0.3118 (3)	1.2055 (2)	−0.14520 (15)	0.0504 (4)
N3	0.3703 (3)	1.27679 (19)	0.27422 (15)	0.0493 (4)
C1	0.2578 (3)	0.9980 (2)	0.14017 (16)	0.0378 (4)
C2	0.2210 (3)	0.9060 (2)	0.01717 (16)	0.0361 (4)
C3	0.2373 (3)	0.9734 (2)	−0.07340 (16)	0.0384 (4)
H3	0.2070	0.9083	−0.1510	0.046*
C4	0.2983 (3)	1.1372 (2)	−0.04913 (15)	0.0379 (4)
C5	0.3457 (3)	1.2371 (2)	0.06573 (16)	0.0379 (4)
H5	0.3911	1.3480	0.0817	0.045*
C6	0.3241 (3)	1.1688 (2)	0.15443 (15)	0.0365 (4)
N4	0.0594 (3)	0.6685 (2)	0.29316 (15)	0.0474 (4)
H4A	0.129 (3)	0.758 (3)	0.2649 (19)	0.057 (6)*
H4B	−0.035 (4)	0.596 (3)	0.237 (2)	0.062 (7)*
C7	0.2150 (4)	0.6041 (3)	0.32664 (19)	0.0566 (6)
H7A	0.2843	0.5754	0.2596	0.068*
H7B	0.1417	0.5077	0.3488	0.068*
C8	0.3775 (4)	0.7270 (3)	0.4274 (2)	0.0594 (6)
H8A	0.4643	0.8164	0.4011	0.071*
H8B	0.4684	0.6791	0.4523	0.071*
C9	0.2784 (3)	0.7893 (3)	0.53097 (18)	0.0526 (5)
H9A	0.3874	0.8743	0.5915	0.063*
H9B	0.2056	0.7032	0.5639	0.063*
C10	0.1237 (3)	0.8534 (2)	0.49162 (18)	0.0493 (5)
H10A	0.0567	0.8894	0.5577	0.059*
H10B	0.1989	0.9451	0.4646	0.059*
C11	−0.0417 (3)	0.7264 (3)	0.39441 (19)	0.0515 (5)
H11A	−0.1225	0.6371	0.4225	0.062*
H11B	−0.1376	0.7703	0.3695	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0884 (11)	0.0402 (8)	0.0443 (8)	0.0175 (7)	0.0082 (7)	0.0180 (6)
O2	0.0997 (13)	0.0396 (8)	0.0693 (11)	0.0220 (8)	0.0124 (9)	0.0194 (8)
O3	0.1180 (15)	0.0386 (8)	0.0531 (10)	0.0173 (9)	−0.0039 (9)	−0.0050 (7)
O4	0.1092 (14)	0.0771 (11)	0.0394 (9)	0.0413 (10)	0.0112 (9)	0.0205 (8)
O5	0.1179 (15)	0.0522 (10)	0.0612 (10)	0.0294 (10)	−0.0006 (10)	0.0274 (8)
O6	0.0848 (12)	0.0457 (9)	0.0602 (10)	0.0046 (9)	−0.0138 (9)	−0.0019 (8)
O7	0.1212 (16)	0.0687 (11)	0.0554 (10)	0.0323 (11)	0.0412 (11)	0.0125 (9)
N1	0.0465 (9)	0.0339 (8)	0.0492 (10)	0.0093 (7)	0.0099 (7)	0.0076 (8)
N2	0.0569 (10)	0.0527 (10)	0.0430 (10)	0.0197 (8)	0.0025 (8)	0.0189 (8)
N3	0.0705 (12)	0.0376 (9)	0.0406 (9)	0.0229 (9)	0.0033 (8)	0.0106 (7)
C1	0.0349 (9)	0.0346 (9)	0.0416 (10)	0.0102 (7)	0.0041 (7)	0.0123 (8)
C2	0.0307 (8)	0.0297 (9)	0.0429 (10)	0.0082 (7)	0.0039 (7)	0.0078 (7)
C3	0.0321 (9)	0.0413 (10)	0.0363 (9)	0.0125 (8)	0.0022 (7)	0.0053 (8)
C4	0.0354 (9)	0.0421 (10)	0.0371 (10)	0.0143 (8)	0.0030 (7)	0.0143 (8)
C5	0.0368 (9)	0.0322 (9)	0.0437 (10)	0.0123 (7)	0.0037 (7)	0.0116 (8)
C6	0.0368 (9)	0.0341 (9)	0.0357 (9)	0.0131 (7)	0.0027 (7)	0.0067 (7)
N4	0.0623 (11)	0.0318 (8)	0.0406 (9)	0.0120 (8)	−0.0057 (8)	0.0090 (8)
C7	0.0780 (15)	0.0478 (12)	0.0519 (12)	0.0346 (11)	0.0098 (11)	0.0128 (10)
C8	0.0520 (12)	0.0671 (14)	0.0616 (13)	0.0298 (11)	0.0035 (10)	0.0143 (11)
C9	0.0560 (12)	0.0538 (12)	0.0426 (11)	0.0182 (10)	−0.0030 (9)	0.0111 (9)
C10	0.0548 (12)	0.0476 (11)	0.0454 (11)	0.0221 (9)	0.0098 (9)	0.0103 (9)
C11	0.0448 (11)	0.0549 (12)	0.0566 (12)	0.0189 (9)	0.0041 (9)	0.0205 (10)

Geometric parameters (Å, º)

O1—C1	1.242 (2)	N4—C11	1.488 (3)
O2—N1	1.228 (2)	N4—C7	1.494 (3)
O3—N1	1.216 (2)	N4—H4A	0.96 (2)
O4—N2	1.222 (2)	N4—H4B	0.86 (3)
O5—N2	1.228 (2)	C7—C8	1.502 (3)
O6—N3	1.215 (2)	C7—H7A	0.9700
O7—N3	1.208 (2)	C7—H7B	0.9700
N1—C2	1.449 (2)	C8—C9	1.513 (3)
N2—C4	1.442 (2)	C8—H8A	0.9700
N3—C6	1.460 (2)	C8—H8B	0.9700
C1—C2	1.450 (3)	C9—C10	1.513 (3)
C1—C6	1.452 (2)	C9—H9A	0.9700
C2—C3	1.376 (3)	C9—H9B	0.9700
C3—C4	1.376 (3)	C10—C11	1.499 (3)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.387 (3)	C10—H10B	0.9700
C5—C6	1.359 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
O3—N1—O2	122.07 (17)	H4A—N4—H4B	108 (2)
O3—N1—C2	118.30 (17)	N4—C7—C8	110.74 (17)
O2—N1—C2	119.52 (16)	N4—C7—H7A	109.5
O4—N2—O5	122.99 (17)	C8—C7—H7A	109.5
O4—N2—C4	118.35 (17)	N4—C7—H7B	109.5
O5—N2—C4	118.65 (17)	C8—C7—H7B	109.5
O7—N3—O6	123.29 (19)	H7A—C7—H7B	108.1
O7—N3—C6	118.69 (17)	C7—C8—C9	112.20 (19)
O6—N3—C6	117.98 (17)	C7—C8—H8A	109.2
O1—C1—C2	126.65 (16)	C9—C8—H8A	109.2
O1—C1—C6	122.04 (17)	C7—C8—H8B	109.2
C2—C1—C6	111.30 (15)	C9—C8—H8B	109.2
C3—C2—N1	116.15 (16)	H8A—C8—H8B	107.9
C3—C2—C1	123.50 (16)	C8—C9—C10	109.83 (17)
N1—C2—C1	120.35 (16)	C8—C9—H9A	109.7
C2—C3—C4	119.95 (16)	C10—C9—H9A	109.7
C2—C3—H3	120.0	C8—C9—H9B	109.7
C4—C3—H3	120.0	C10—C9—H9B	109.7
C3—C4—C5	121.18 (17)	H9A—C9—H9B	108.2
C3—C4—N2	119.14 (16)	C11—C10—C9	110.90 (17)
C5—C4—N2	119.68 (16)	C11—C10—H10A	109.5
C6—C5—C4	118.38 (16)	C9—C10—H10A	109.5
C6—C5—H5	120.8	C11—C10—H10B	109.5
C4—C5—H5	120.8	C9—C10—H10B	109.5
C5—C6—C1	125.61 (16)	H10A—C10—H10B	108.0
C5—C6—N3	117.05 (15)	N4—C11—C10	109.98 (17)
C1—C6—N3	117.34 (15)	N4—C11—H11A	109.7
C11—N4—C7	112.42 (16)	C10—C11—H11A	109.7
C11—N4—H4A	107.0 (13)	N4—C11—H11B	109.7
C7—N4—H4A	109.8 (13)	C10—C11—H11B	109.7
C11—N4—H4B	110.2 (16)	H11A—C11—H11B	108.2
C7—N4—H4B	109.8 (16)
O3—N1—C2—C3	−13.3 (3)	N2—C4—C5—C6	177.60 (16)
O2—N1—C2—C3	163.00 (17)	C4—C5—C6—C1	1.0 (3)
O3—N1—C2—C1	167.30 (18)	C4—C5—C6—N3	−178.55 (16)
O2—N1—C2—C1	−16.4 (3)	O1—C1—C6—C5	−179.32 (18)
O1—C1—C2—C3	177.71 (18)	C2—C1—C6—C5	1.4 (3)
C6—C1—C2—C3	−3.1 (2)	O1—C1—C6—N3	0.2 (3)
O1—C1—C2—N1	−2.9 (3)	C2—C1—C6—N3	−179.03 (15)
C6—C1—C2—N1	176.32 (15)	O7—N3—C6—C5	128.9 (2)
N1—C2—C3—C4	−177.11 (15)	O6—N3—C6—C5	−48.8 (2)
C1—C2—C3—C4	2.3 (3)	O7—N3—C6—C1	−50.7 (2)
C2—C3—C4—C5	0.4 (3)	O6—N3—C6—C1	131.57 (18)
C2—C3—C4—N2	−179.18 (16)	C11—N4—C7—C8	−54.9 (2)
O4—N2—C4—C3	−8.8 (3)	N4—C7—C8—C9	53.5 (3)
O5—N2—C4—C3	170.78 (18)	C7—C8—C9—C10	−54.7 (2)
O4—N2—C4—C5	171.52 (18)	C8—C9—C10—C11	56.9 (2)
O5—N2—C4—C5	−8.9 (3)	C7—N4—C11—C10	57.4 (2)
C3—C4—C5—C6	−2.0 (3)	C9—C10—C11—N4	−58.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1	0.96 (2)	1.82 (2)	2.767 (2)	171 (2)
N4—H4A···O2	0.96 (2)	2.50 (2)	2.996 (3)	112.0 (16)
N4—H4B···O3^i	0.86 (3)	2.28 (3)	2.970 (2)	138 (2)
C8—H8A···O4^ii	0.97	2.58	3.399 (3)	142
C10—H10A···O7^iii	0.97	2.53	3.290 (3)	135
C11—H11B···O4^iv	0.97	2.44	3.361 (3)	157

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