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.
Supporting information
CCDC reference: 605078
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
top
Crystal data top
C18H20N42+·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) Å3 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0388P)2 + 0.1613P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C11i | 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—C11i | 111.24 (14) |
C4—C5—H5 | 121.8 | C10—C11—H11B | 109.4 |
C5—C6—C7 | 121.81 (13) | C11i—C11—H11B | 109.4 |
C5—C6—H6 | 119.1 | C10—C11—H11A | 109.4 |
C7—C6—H6 | 119.1 | C11i—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—C11i | 177.23 (14) |
Symmetry code: (i) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
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···Cl1ii | 0.97 | 2.19 | 3.1563 (12) | 174 |
N1—H1···O1Wiii | 0.88 | 1.94 | 2.7433 (17) | 151 |
Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1. |