2,2′-(Butane-1,4-di­yl)dibenzimidazolium dichloride dihydrate

In the title compound, C₁₈H₂₄Cl₂N₄O₂, a quarternary adduct consisting of two water mol­ecules and two chloride ions binds the centrosymmetric 2,2′-(butane-1,4-di­yl)dibenzimidazolium cations into two-dimensional hydrogen-bonded layers.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.087
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED.

2,2'-(Butane-1,4-diyl)dibenzimidazolium dichloride dihydrate

Crystal data

C18H20N4^2+·2Cl^−·2H2O	Z = 1
Mr = 399.31	F(000) = 210
Triclinic, P1	Dx = 1.425 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9671 (5) Å	Cell parameters from 1899 reflections
b = 8.6567 (7) Å	θ = 3.1–27.8°
c = 8.8036 (7) Å	µ = 0.37 mm^−1
α = 69.342 (1)°	T = 100 K
β = 79.171 (1)°	Block, colourless
γ = 69.886 (1)°	0.38 × 0.30 × 0.23 mm
V = 465.18 (6) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	1939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 28.3°, θmin = 2.5°
ω scans	h = −9→8
5344 measured reflections	k = −11→11
2129 independent reflections	l = −11→11

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) = 0.087	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.1613P] where P = (Fo^2 + 2Fc^2)/3
2129 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.26 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	0.06756 (5)	0.81786 (4)	0.77709 (4)	0.01620 (12)
N1	0.38836 (18)	0.26755 (14)	0.58203 (13)	0.0123 (2)
H1	0.4601	0.1593	0.5910	0.015*
C2	0.3241 (2)	0.33368 (17)	0.70499 (16)	0.0125 (3)
N3	0.22114 (18)	0.50134 (14)	0.64659 (14)	0.0129 (2)
H3	0.1644	0.5719	0.7051	0.015*
C4	0.2177 (2)	0.54689 (17)	0.47906 (16)	0.0125 (3)
C5	0.1315 (2)	0.70325 (18)	0.36190 (17)	0.0144 (3)
H5	0.0599	0.8060	0.3897	0.017*
C6	0.1558 (2)	0.70084 (18)	0.20302 (17)	0.0155 (3)
H6	0.0991	0.8047	0.1196	0.019*
C7	0.2621 (2)	0.54892 (18)	0.16166 (17)	0.0161 (3)
H7	0.2742	0.5525	0.0512	0.019*
C8	0.3495 (2)	0.39419 (18)	0.27782 (17)	0.0154 (3)
H8	0.4228	0.2918	0.2499	0.018*
H1W	0.2287	0.9497	0.5592	0.046 (6)*
H2W	0.1885	1.0684	0.3796	0.047 (6)*
C9	0.3243 (2)	0.39651 (17)	0.43747 (16)	0.0128 (3)
C10	0.3598 (2)	0.23669 (17)	0.87950 (16)	0.0136 (3)
H10A	0.2258	0.2463	0.9437	0.016*
H10B	0.4360	0.2912	0.9187	0.016*
C11	0.4794 (2)	0.04548 (17)	0.91023 (16)	0.0148 (3)
H11B	0.6114	0.0347	0.8430	0.018*
H11A	0.4004	−0.0116	0.8772	0.018*
O1W	0.29167 (15)	1.01151 (13)	0.45762 (12)	0.0168 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0197 (2)	0.01332 (18)	0.01238 (17)	−0.00026 (13)	−0.00332 (12)	−0.00381 (12)
N1	0.0138 (6)	0.0092 (5)	0.0117 (5)	−0.0007 (4)	−0.0023 (4)	−0.0028 (4)
C2	0.0111 (6)	0.0122 (6)	0.0142 (6)	−0.0036 (5)	−0.0011 (5)	−0.0040 (5)
N3	0.0144 (6)	0.0107 (5)	0.0127 (6)	−0.0020 (5)	−0.0015 (4)	−0.0040 (4)
C4	0.0109 (6)	0.0136 (6)	0.0139 (6)	−0.0042 (5)	−0.0015 (5)	−0.0046 (5)
C5	0.0130 (6)	0.0110 (6)	0.0184 (7)	−0.0025 (5)	−0.0029 (5)	−0.0039 (5)
C6	0.0139 (7)	0.0133 (6)	0.0164 (7)	−0.0040 (5)	−0.0046 (5)	0.0005 (5)
C7	0.0167 (7)	0.0183 (7)	0.0131 (7)	−0.0057 (6)	−0.0028 (5)	−0.0033 (5)
C8	0.0165 (7)	0.0142 (7)	0.0155 (7)	−0.0034 (5)	−0.0021 (5)	−0.0055 (5)
C9	0.0112 (6)	0.0113 (6)	0.0145 (7)	−0.0028 (5)	−0.0020 (5)	−0.0023 (5)
C10	0.0154 (7)	0.0125 (6)	0.0113 (6)	−0.0027 (5)	−0.0014 (5)	−0.0031 (5)
C11	0.0181 (7)	0.0134 (7)	0.0109 (7)	−0.0027 (5)	−0.0023 (5)	−0.0029 (5)
O1W	0.0160 (5)	0.0153 (5)	0.0167 (5)	−0.0012 (4)	−0.0033 (4)	−0.0046 (4)

Geometric parameters (Å, º)

N1—C2	1.3337 (17)	C7—C8	1.3846 (19)
N1—C9	1.3905 (17)	C7—H7	0.9500
N1—H1	0.8800	C8—C9	1.3897 (19)
C2—N3	1.3346 (17)	C8—H8	0.9500
C2—C10	1.4890 (18)	C10—C11	1.5255 (18)
N3—C4	1.3885 (17)	C10—H10A	0.9900
N3—H3	0.8800	C10—H10B	0.9900
C4—C5	1.3947 (19)	C11—C11^i	1.529 (3)
C4—C9	1.3962 (19)	C11—H11B	0.9900
C5—C6	1.384 (2)	C11—H11A	0.9900
C5—H5	0.9500	O1W—H1W	0.9772
C6—C7	1.406 (2)	O1W—H2W	0.9665
C6—H6	0.9500
C2—N1—C9	109.29 (11)	C6—C7—H7	119.2
C2—N1—H1	125.4	C7—C8—C9	116.51 (13)
C9—N1—H1	125.4	C7—C8—H8	121.7
N1—C2—N3	108.97 (12)	C9—C8—H8	121.7
N1—C2—C10	125.75 (12)	C8—C9—N1	131.87 (12)
N3—C2—C10	125.28 (12)	C8—C9—C4	121.97 (13)
C2—N3—C4	109.31 (11)	N1—C9—C4	106.16 (12)
C2—N3—H3	125.3	C2—C10—C11	113.52 (11)
C4—N3—H3	125.3	C2—C10—H10A	108.9
N3—C4—C5	132.17 (13)	C11—C10—H10A	108.9
N3—C4—C9	106.25 (12)	C2—C10—H10B	108.9
C5—C4—C9	121.57 (13)	C11—C10—H10B	108.9
C6—C5—C4	116.49 (13)	H10A—C10—H10B	107.7
C6—C5—H5	121.8	C10—C11—C11^i	111.24 (14)
C4—C5—H5	121.8	C10—C11—H11B	109.4
C5—C6—C7	121.81 (13)	C11^i—C11—H11B	109.4
C5—C6—H6	119.1	C10—C11—H11A	109.4
C7—C6—H6	119.1	C11^i—C11—H11A	109.4
C8—C7—C6	121.66 (13)	H11B—C11—H11A	108.0
C8—C7—H7	119.2	H1W—O1W—H2W	107.5
C9—N1—C2—N3	−0.32 (16)	C7—C8—C9—N1	179.38 (14)
C9—N1—C2—C10	179.37 (13)	C7—C8—C9—C4	−0.4 (2)
N1—C2—N3—C4	0.03 (16)	C2—N1—C9—C8	−179.31 (15)
C10—C2—N3—C4	−179.67 (12)	C2—N1—C9—C4	0.48 (15)
C2—N3—C4—C5	179.88 (14)	N3—C4—C9—C8	179.37 (12)
C2—N3—C4—C9	0.27 (15)	C5—C4—C9—C8	−0.3 (2)
N3—C4—C5—C6	−179.02 (14)	N3—C4—C9—N1	−0.45 (15)
C9—C4—C5—C6	0.5 (2)	C5—C4—C9—N1	179.89 (12)
C4—C5—C6—C7	−0.1 (2)	N1—C2—C10—C11	−0.7 (2)
C5—C6—C7—C8	−0.6 (2)	N3—C2—C10—C11	178.92 (13)
C6—C7—C8—C9	0.8 (2)	C2—C10—C11—C11^i	177.23 (14)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1	0.88	2.28	3.1169 (13)	159
O1W—H1W···Cl1	0.98	2.18	3.1594 (11)	176
O1W—H2W···Cl1^ii	0.97	2.19	3.1563 (12)	174
N1—H1···O1W^iii	0.88	1.94	2.7433 (17)	151

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