3-Methyl-1-(3-methyl­pyridinium-4-yl)pyridinium dichloride monohydrate

The asymmetric unit of the title compound, C₁₂H₁₄N₂²⁺·2Cl^-·H₂O, comprises a pyridinium dication, two independent Cl^- anions and a water mol­ecule. The three components are linked through hydrogen bonding and are packed to form a discrete halide salt structure.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.108
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.08
           From the CIF: _diffrn_reflns_theta_full          28.10
           From the CIF: _reflns_number_total               3052
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3242
           Completeness (_total/calc)             94.14%
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   2 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Version 1.4; Bruno et al., 2002).

3-Methyl-1-(3-methylpyridinium-4-yl)pyridinium dichloride monohydrate

Crystal data

C12H14N2^2+·2Cl^−·H2O	Z = 2
Mr = 275.17	F(000) = 288
Triclinic, P1	Dx = 1.372 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3062 (8) Å	Cell parameters from 2766 reflections
b = 7.9701 (8) Å	θ = 2.7–27.8°
c = 12.7134 (13) Å	µ = 0.47 mm^−1
α = 78.987 (2)°	T = 105 K
β = 74.273 (2)°	Flat needle, colourless
γ = 70.079 (2)°	0.55 × 0.26 × 0.10 mm
V = 665.97 (12) Å^3

Data collection

Bruker SMART 1000 CCD diffractometer	3052 independent reflections
Radiation source: fine-focus sealed tube	2616 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 28.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.785, Tmax = 0.950	k = −10→10
6341 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0137P)^2 + 1.3181P] where P = (Fo^2 + 2Fc^2)/3
3052 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. In a thin film of perfluoropolyether oil on a mohair fibre.

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
O20	0.6764 (3)	0.7577 (3)	0.70273 (17)	0.0264 (4)
H20	0.729 (5)	0.646 (5)	0.731 (3)	0.040*
H21	0.763 (6)	0.800 (5)	0.698 (3)	0.040*
Cl1	0.86086 (9)	0.37841 (8)	0.83333 (5)	0.01867 (15)
H50	0.140 (5)	0.097 (4)	1.117 (3)	0.028*
Cl2	0.01971 (9)	0.91059 (8)	0.71411 (5)	0.01997 (15)
N1	0.4293 (3)	0.2080 (3)	0.71955 (16)	0.0147 (4)
N2	0.1958 (3)	0.1111 (3)	1.05127 (18)	0.0197 (5)
C1	0.5714 (4)	0.2593 (3)	0.4985 (2)	0.0183 (5)
H1	0.6199	0.2771	0.4212	0.022*
C2	0.3962 (4)	0.2158 (3)	0.5395 (2)	0.0192 (5)
H2	0.3245	0.2042	0.4906	0.023*
C3	0.3250 (4)	0.1892 (3)	0.6515 (2)	0.0174 (5)
H3	0.2050	0.1583	0.6805	0.021*
C4	0.6024 (3)	0.2507 (3)	0.6816 (2)	0.0154 (5)
H4	0.6715	0.2623	0.7319	0.018*
C5	0.6784 (4)	0.2774 (3)	0.5693 (2)	0.0165 (5)
C6	0.3545 (3)	0.1762 (3)	0.83697 (19)	0.0156 (5)
C7	0.3318 (4)	0.0083 (3)	0.8776 (2)	0.0178 (5)
H7	0.3720	−0.0834	0.8305	0.021*
C8	0.2495 (4)	−0.0222 (3)	0.9879 (2)	0.0195 (5)
H8	0.2311	−0.1353	1.0185	0.023*
C9	0.2195 (3)	0.2720 (3)	1.0133 (2)	0.0169 (5)
H9	0.1806	0.3601	1.0626	0.020*
C10	0.3002 (3)	0.3137 (3)	0.9027 (2)	0.0152 (5)
C11	0.8730 (4)	0.3179 (4)	0.5288 (2)	0.0224 (5)
H11A	0.8889	0.3839	0.5816	0.034*
H11B	0.8744	0.3911	0.4574	0.034*
H11C	0.9830	0.2054	0.5208	0.034*
C12	0.3118 (4)	0.5000 (3)	0.8616 (2)	0.0203 (5)
H12A	0.4520	0.4975	0.8402	0.030*
H12B	0.2401	0.5786	0.9200	0.030*
H12C	0.2509	0.5457	0.7978	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O20	0.0259 (11)	0.0299 (11)	0.0240 (10)	−0.0080 (9)	−0.0088 (8)	−0.0005 (8)
Cl1	0.0185 (3)	0.0191 (3)	0.0205 (3)	−0.0065 (2)	−0.0056 (2)	−0.0038 (2)
Cl2	0.0226 (3)	0.0212 (3)	0.0151 (3)	−0.0087 (2)	0.0007 (2)	−0.0031 (2)
N1	0.0151 (10)	0.0165 (10)	0.0117 (9)	−0.0051 (8)	−0.0013 (8)	−0.0013 (8)
N2	0.0154 (10)	0.0292 (12)	0.0126 (10)	−0.0069 (9)	−0.0013 (8)	−0.0001 (9)
C1	0.0199 (12)	0.0201 (12)	0.0134 (11)	−0.0044 (10)	−0.0029 (9)	−0.0022 (9)
C2	0.0180 (12)	0.0240 (13)	0.0163 (12)	−0.0043 (10)	−0.0052 (10)	−0.0059 (10)
C3	0.0150 (11)	0.0220 (12)	0.0175 (12)	−0.0069 (9)	−0.0037 (9)	−0.0051 (10)
C4	0.0124 (11)	0.0167 (11)	0.0176 (11)	−0.0043 (9)	−0.0033 (9)	−0.0034 (9)
C5	0.0150 (11)	0.0157 (11)	0.0171 (12)	−0.0032 (9)	−0.0018 (9)	−0.0030 (9)
C6	0.0117 (11)	0.0222 (12)	0.0128 (11)	−0.0058 (9)	−0.0031 (9)	−0.0002 (9)
C7	0.0167 (12)	0.0185 (12)	0.0189 (12)	−0.0050 (9)	−0.0050 (9)	−0.0030 (10)
C8	0.0177 (12)	0.0206 (12)	0.0195 (12)	−0.0071 (10)	−0.0038 (10)	0.0013 (10)
C9	0.0139 (11)	0.0216 (12)	0.0153 (11)	−0.0039 (9)	−0.0030 (9)	−0.0058 (10)
C10	0.0109 (10)	0.0190 (12)	0.0166 (11)	−0.0047 (9)	−0.0046 (9)	−0.0016 (9)
C11	0.0188 (13)	0.0313 (14)	0.0187 (12)	−0.0128 (11)	−0.0003 (10)	−0.0022 (11)
C12	0.0184 (12)	0.0176 (12)	0.0240 (13)	−0.0051 (10)	−0.0017 (10)	−0.0054 (10)

Geometric parameters (Å, º)

O20—H20	0.89 (4)	C5—C11	1.498 (3)
O20—H21	0.80 (4)	C6—C7	1.388 (3)
N1—C3	1.355 (3)	C6—C10	1.389 (3)
N1—C4	1.360 (3)	C7—C8	1.378 (3)
N1—C6	1.449 (3)	C7—H7	0.9500
N2—C9	1.334 (3)	C8—H8	0.9500
N2—C8	1.342 (3)	C9—C10	1.393 (3)
N2—H50	0.83 (3)	C9—H9	0.9500
C1—C2	1.379 (4)	C10—C12	1.500 (3)
C1—C5	1.396 (3)	C11—H11A	0.9800
C1—H1	0.9500	C11—H11B	0.9800
C2—C3	1.379 (3)	C11—H11C	0.9800
C2—H2	0.9500	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.388 (3)	C12—H12C	0.9800
C4—H4	0.9500
H20—O20—H21	101 (3)	C8—C7—C6	118.3 (2)
C3—N1—C4	122.5 (2)	C8—C7—H7	120.9
C3—N1—C6	118.1 (2)	C6—C7—H7	120.9
C4—N1—C6	119.4 (2)	N2—C8—C7	118.8 (2)
C9—N2—C8	123.4 (2)	N2—C8—H8	120.6
C9—N2—H50	117 (2)	C7—C8—H8	120.6
C8—N2—H50	120 (2)	N2—C9—C10	121.3 (2)
C2—C1—C5	120.7 (2)	N2—C9—H9	119.3
C2—C1—H1	119.7	C10—C9—H9	119.3
C5—C1—H1	119.7	C6—C10—C9	115.3 (2)
C1—C2—C3	120.1 (2)	C6—C10—C12	124.9 (2)
C1—C2—H2	119.9	C9—C10—C12	119.8 (2)
C3—C2—H2	119.9	C5—C11—H11A	109.5
N1—C3—C2	118.8 (2)	C5—C11—H11B	109.5
N1—C3—H3	120.6	H11A—C11—H11B	109.5
C2—C3—H3	120.6	C5—C11—H11C	109.5
N1—C4—C5	120.1 (2)	H11A—C11—H11C	109.5
N1—C4—H4	120.0	H11B—C11—H11C	109.5
C5—C4—H4	120.0	C10—C12—H12A	109.5
C4—C5—C1	117.9 (2)	C10—C12—H12B	109.5
C4—C5—C11	119.4 (2)	H12A—C12—H12B	109.5
C1—C5—C11	122.7 (2)	C10—C12—H12C	109.5
C7—C6—C10	123.0 (2)	H12A—C12—H12C	109.5
C7—C6—N1	117.0 (2)	H12B—C12—H12C	109.5
C10—C6—N1	119.9 (2)
C10—C6—N1—C4	62.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···Cl1	0.89 (4)	2.32 (4)	3.199 (2)	170 (3)
O20—H21···Cl2^i	0.80 (4)	2.40 (4)	3.185 (2)	171 (4)
N2—H50···Cl2^ii	0.83 (3)	2.15 (3)	2.975 (2)	174 (3)

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