Bis(piperidinium) chloranilate

In the title crystal structure, 2C₅H₁₂N⁺·C₆Cl₂O₄²⁻, chloranilate and piperidinium ions are connected by bifurcated N—H...O hydrogen bonds, giving a centrosymmetric chloranirate–piperidinium 1:2 unit. The 1:2 units are connected to each other by N—H...O hydrogen bonds, forming a mol­ecular ladder. There is a centre of symmetry at the centre of the anion ring.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.083
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.781     0.968
            Tmin(prime) and Tmax expected:      0.889     0.968
            RR(prime) =      0.878
            Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C1     -C3_a          1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C1     -C3_a          0.16 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C3_a   ...       1.54 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C5 H12 N

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Bis(piperidinium) chloranilate

Crystal data

2C5H12N^+·C6Cl2O4^2^−	Z = 1
Mr = 379.28	F(000) = 200.00
Triclinic, P1	Dx = 1.506 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 5.1239 (3) Å	Cell parameters from 3435 reflections
b = 8.7058 (7) Å	θ = 4.0–27.1°
c = 10.4508 (7) Å	µ = 0.41 mm^−1
α = 114.412 (3)°	T = 100 K
β = 95.561 (2)°	Prism, dark red
γ = 95.070 (3)°	0.28 × 0.15 × 0.08 mm
V = 418.25 (5) Å^3

Data collection

Rigaku R-AXIS RAPID II diffractometer	1534 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.045
ω scans	θmax = 27.1°, θmin = 4.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.781, Tmax = 0.968	k = −11→11
4040 measured reflections	l = −13→13
1838 independent 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0364P)^2 + 0.1379P] where P = (Fo^2 + 2Fc^2)/3
1838 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.38 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
Cl1	0.96700 (7)	0.57847 (5)	0.75158 (4)	0.01542 (13)
O1	0.7985 (2)	0.25722 (14)	0.48983 (13)	0.0164 (3)
O2	0.5894 (2)	0.81395 (14)	0.72451 (12)	0.0145 (3)
N1	0.8960 (3)	0.01402 (17)	0.22845 (15)	0.0124 (3)
C1	0.6672 (3)	0.37303 (19)	0.49911 (17)	0.0112 (3)
C2	0.7079 (3)	0.5373 (2)	0.61515 (17)	0.0122 (3)
C3	0.5576 (3)	0.6656 (2)	0.62425 (17)	0.0123 (3)
C4	0.9625 (3)	−0.0916 (2)	0.30577 (18)	0.0146 (3)
C5	0.7119 (3)	−0.1972 (2)	0.30728 (19)	0.0152 (3)
C6	0.5820 (3)	−0.3121 (2)	0.15509 (19)	0.0165 (4)
C7	0.5266 (3)	−0.2076 (2)	0.07122 (18)	0.0154 (4)
C8	0.7743 (3)	−0.0928 (2)	0.07768 (18)	0.0135 (3)
H1	0.785 (4)	0.081 (3)	0.274 (2)	0.027 (6)*
H2	1.036 (4)	0.079 (3)	0.234 (2)	0.016 (5)*
H3	1.051 (4)	−0.015 (3)	0.397 (2)	0.017 (5)*
H4	1.093 (4)	−0.167 (3)	0.255 (2)	0.018 (5)*
H5	0.587 (4)	−0.120 (3)	0.359 (2)	0.017 (5)*
H6	0.752 (4)	−0.265 (3)	0.357 (2)	0.025 (5)*
H7	0.413 (4)	−0.377 (3)	0.153 (2)	0.027 (6)*
H8	0.704 (4)	−0.394 (3)	0.108 (2)	0.025 (5)*
H9	0.391 (4)	−0.135 (3)	0.112 (2)	0.015 (5)*
H10	0.465 (4)	−0.278 (2)	−0.027 (2)	0.009 (4)*
H11	0.737 (4)	−0.015 (2)	0.036 (2)	0.010 (4)*
H12	0.913 (4)	−0.162 (3)	0.032 (2)	0.017 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0148 (2)	0.0141 (2)	0.0141 (2)	0.00190 (14)	−0.00284 (15)	0.00393 (15)
O1	0.0181 (6)	0.0127 (5)	0.0163 (6)	0.0058 (5)	0.0010 (5)	0.0038 (5)
O2	0.0141 (5)	0.0097 (5)	0.0148 (6)	0.0010 (4)	0.0008 (5)	0.0010 (5)
N1	0.0127 (6)	0.0089 (6)	0.0133 (7)	−0.0010 (6)	0.0016 (6)	0.0030 (5)
C1	0.0116 (7)	0.0101 (7)	0.0123 (7)	0.0001 (6)	0.0028 (6)	0.0052 (6)
C2	0.0105 (7)	0.0133 (7)	0.0104 (7)	0.0002 (6)	−0.0020 (6)	0.0036 (6)
C3	0.0116 (7)	0.0096 (7)	0.0139 (8)	−0.0014 (6)	0.0029 (6)	0.0036 (6)
C4	0.0146 (8)	0.0159 (8)	0.0121 (8)	0.0015 (6)	−0.0012 (6)	0.0057 (6)
C5	0.0161 (8)	0.0152 (8)	0.0165 (8)	0.0022 (6)	0.0017 (7)	0.0090 (7)
C6	0.0156 (8)	0.0125 (7)	0.0197 (8)	−0.0005 (7)	−0.0008 (7)	0.0066 (7)
C7	0.0135 (7)	0.0141 (8)	0.0149 (8)	−0.0005 (6)	−0.0021 (7)	0.0039 (6)
C8	0.0140 (8)	0.0140 (8)	0.0126 (8)	0.0018 (6)	0.0012 (6)	0.0061 (6)

Geometric parameters (Å, º)

Cl1—C2	1.7466 (16)	C4—H4	1.01 (2)
O1—C1	1.2372 (19)	C5—C6	1.528 (2)
O2—C3	1.2662 (18)	C5—H5	1.00 (2)
N1—C4	1.493 (2)	C5—H6	0.96 (2)
N1—C8	1.494 (2)	C6—C7	1.527 (3)
N1—H1	0.88 (2)	C6—H7	0.98 (2)
N1—H2	0.86 (2)	C6—H8	0.99 (2)
C1—C2	1.423 (2)	C7—C8	1.522 (2)
C1—C3^i	1.545 (2)	C7—H9	0.99 (2)
C2—C3	1.389 (2)	C7—H10	0.958 (19)
C3—C1^i	1.545 (2)	C8—H11	0.97 (2)
C4—C5	1.517 (2)	C8—H12	1.00 (2)
C4—H3	0.95 (2)
Cl1···N1^ii	3.4702 (17)	O1···H1	2.13 (2)
Cl1···C1^ii	3.5045 (17)	O1···H2	2.93 (2)
O1···N1	2.8045 (19)	O1···H3	2.67 (2)
O1···C4	3.093 (2)	O1···H3^iii	2.93 (2)
O1···C4^iii	3.239 (2)	O1···H6^iii	2.65 (2)
O2···N1^i	2.9929 (19)	O2···H1^i	2.20 (2)
O2···N1^ii	2.8070 (19)	O2···H2^ii	1.98 (2)
O2···C4^ii	3.318 (2)	O2···H9^i	2.59 (2)
O2···C8^i	3.322 (2)	O2···H11^vi	2.95 (2)
Cl1···H2^ii	2.93 (3)	N1···H9^vii	3.08 (2)
Cl1···H6^iii	3.04 (2)	N1···H11^viii	3.49 (2)
Cl1···H7^iv	3.01 (2)	C1···H1	2.82 (2)
Cl1···H8^iii	3.09 (2)	C3···H1^i	2.86 (2)
Cl1···H10^v	3.05 (2)	C3···H2^ii	2.71 (2)
Cl1···H12^vi	2.93 (2)	C4···H3^iii	2.86 (2)
C4—N1—C8	112.14 (13)	C6—C5—H5	110.0 (12)
C4—N1—H1	107.4 (15)	C4—C5—H6	110.3 (13)
C8—N1—H1	110.0 (14)	C6—C5—H6	109.9 (13)
C4—N1—H2	108.7 (14)	H5—C5—H6	107.3 (18)
C8—N1—H2	111.7 (14)	C7—C6—C5	111.01 (14)
H1—N1—H2	106.7 (19)	C7—C6—H7	108.0 (14)
O1—C1—C2	124.61 (15)	C5—C6—H7	111.4 (13)
O1—C1—C3^i	117.11 (13)	C7—C6—H8	109.0 (14)
C2—C1—C3^i	118.28 (14)	C5—C6—H8	108.8 (12)
C3—C2—C1	123.88 (15)	H7—C6—H8	108.5 (18)
C3—C2—Cl1	118.86 (12)	C8—C7—C6	111.68 (14)
C1—C2—Cl1	117.24 (12)	C8—C7—H9	108.1 (12)
O2—C3—C2	125.90 (15)	C6—C7—H9	109.4 (12)
O2—C3—C1^i	116.26 (14)	C8—C7—H10	106.7 (11)
C2—C3—C1^i	117.84 (13)	C6—C7—H10	112.2 (12)
N1—C4—C5	109.50 (13)	H9—C7—H10	108.7 (15)
N1—C4—H3	106.5 (13)	N1—C8—C7	110.41 (14)
C5—C4—H3	114.4 (12)	N1—C8—H11	106.6 (11)
N1—C4—H4	107.7 (12)	C7—C8—H11	112.6 (11)
C5—C4—H4	111.1 (12)	N1—C8—H12	105.3 (11)
H3—C4—H4	107.3 (16)	C7—C8—H12	110.9 (11)
C4—C5—C6	109.84 (14)	H11—C8—H12	110.7 (16)
C4—C5—H5	109.5 (12)
O1—C1—C2—C3	−179.65 (16)	Cl1—C2—C3—C1^i	178.92 (11)
C3^i—C1—C2—C3	−0.1 (3)	C8—N1—C4—C5	−60.58 (17)
O1—C1—C2—Cl1	1.5 (2)	N1—C4—C5—C6	59.06 (17)
C3^i—C1—C2—Cl1	−178.94 (11)	C4—C5—C6—C7	−56.11 (18)
C1—C2—C3—O2	−179.03 (16)	C5—C6—C7—C8	53.38 (18)
Cl1—C2—C3—O2	−0.2 (2)	C4—N1—C8—C7	57.27 (17)
C1—C2—C3—C1^i	0.1 (3)	C6—C7—C8—N1	−53.13 (18)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88 (2)	2.13 (2)	2.8045 (19)	133.1 (17)
N1—H1···O2^i	0.88 (2)	2.20 (2)	2.9929 (19)	150.7 (17)
N1—H2···O2^ii	0.86 (2)	1.98 (2)	2.8070 (19)	162 (2)
C7—H9···O2^i	0.99 (2)	2.59 (2)	3.349 (2)	133.5 (17)

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