3,3′-(1,4-Naphthalene­dimethyl­ene)bis­(1-methyl­imidazolium) diiodide monohydrate

In the title compound, C₂₀H₂₂N₄²⁺·2I⁻·H₂O, the two imidazolium rings are twisted away from the central naphthalene plane by 76.6 (1) and 74.5 (1)°. The crystal packing is stabilized by O—H...I, C—H...O and C—H...I hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT732_ALERT_1_C Angle   Calc      108(7), Rep      107(3) ......       2.33 su-Rat
              H1W  -O1W  -H2W     1.555   1.555   1.555

   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

   2 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: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: SHELXL97.

3,3'-(1,4-Naphthalenedimethylene)bis(1-methylimidazolium) diiodide monohydrate

Crystal data

C20H22N4^2+·2I^−·H2O	Z = 2
Mr = 590.23	F(000) = 572
Triclinic, P1	Dx = 1.758 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.563 (3) Å	Cell parameters from 18 reflections
b = 9.572 (3) Å	θ = 4.4–7.4°
c = 14.684 (6) Å	µ = 2.84 mm^−1
α = 102.97 (3)°	T = 292 K
β = 103.66 (3)°	Block, yellow
γ = 98.24 (3)°	0.25 × 0.15 × 0.08 mm
V = 1114.9 (7) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2850 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω/2θ scans	h = −10→9
Absorption correction: ψ scan (North et al., 1968)	k = −2→11
Tmin = 0.583, Tmax = 0.797	l = −17→17
3927 measured reflections	3 standard reflections every 300 reflections
3900 independent reflections	intensity decay: 2.1%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
3900 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.48 e Å^−3
3 restraints	Δρmin = −0.51 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
N1	0.4114 (4)	0.7267 (4)	0.2456 (3)	0.0378 (8)
N2	0.3266 (4)	0.6030 (4)	0.3368 (2)	0.0383 (8)
N3	0.0560 (4)	0.8516 (4)	−0.2294 (2)	0.0346 (8)
N4	0.1375 (4)	0.8710 (4)	−0.3542 (3)	0.0396 (9)
C1	0.3350 (5)	0.8589 (4)	0.1186 (3)	0.0343 (9)
C2	0.2037 (5)	0.7473 (5)	0.0667 (3)	0.0410 (10)
H2	0.1875	0.6628	0.0876	0.049*
C3	0.0922 (6)	0.7582 (5)	−0.0181 (3)	0.0435 (11)
H3	0.0037	0.6807	−0.0515	0.052*
C4	0.1106 (5)	0.8793 (5)	−0.0524 (3)	0.0379 (10)
C5	0.2700 (5)	1.1302 (4)	−0.0287 (3)	0.0385 (10)
H5	0.1974	1.1386	−0.0844	0.046*
C6	0.3968 (6)	1.2436 (5)	0.0226 (3)	0.0441 (11)
H6	0.4095	1.3283	0.0017	0.053*
C7	0.5086 (5)	1.2350 (4)	0.1064 (3)	0.0426 (11)
H7	0.5958	1.3131	0.1409	0.051*
C8	0.4886 (5)	1.1103 (4)	0.1373 (3)	0.0366 (9)
H8	0.5623	1.1055	0.1937	0.044*
C9	0.3585 (5)	0.9889 (4)	0.0855 (3)	0.0325 (9)
C10	0.2452 (5)	0.9993 (4)	0.0003 (3)	0.0331 (9)
C11	0.4573 (5)	0.8514 (4)	0.2083 (3)	0.0389 (10)
H11A	0.5619	0.8471	0.1942	0.047*
H11B	0.4729	0.9410	0.2590	0.047*
C12	0.3467 (5)	0.7321 (4)	0.3195 (3)	0.0397 (10)
H12	0.3197	0.8149	0.3539	0.048*
C13	0.3805 (6)	0.5097 (5)	0.2723 (4)	0.0503 (12)
H13	0.3803	0.4114	0.2685	0.060*
C14	0.4341 (7)	0.5857 (5)	0.2149 (4)	0.0563 (13)
H14	0.4780	0.5500	0.1643	0.068*
C15	0.2605 (7)	0.5651 (5)	0.4142 (3)	0.0538 (13)
H15A	0.1590	0.5975	0.4122	0.081*
H15B	0.3381	0.6122	0.4764	0.081*
H15C	0.2413	0.4608	0.4046	0.081*
C16	−0.0105 (5)	0.8845 (5)	−0.1442 (3)	0.0447 (11)
H16A	−0.1113	0.8138	−0.1562	0.054*
H16B	−0.0365	0.9811	−0.1356	0.054*
C17	0.0822 (5)	0.9400 (5)	−0.2834 (3)	0.0378 (10)
H17	0.0648	1.0353	−0.2735	0.045*
C18	0.1421 (6)	0.7319 (5)	−0.3460 (3)	0.0483 (12)
H18	0.1736	0.6590	−0.3870	0.058*
C19	0.0927 (5)	0.7207 (4)	−0.2677 (3)	0.0412 (10)
H19	0.0848	0.6387	−0.2437	0.049*
C20	0.1792 (7)	0.9319 (6)	−0.4308 (4)	0.0590 (14)
H20A	0.1790	1.0348	−0.4155	0.089*
H20B	0.0996	0.8831	−0.4920	0.089*
H20C	0.2863	0.9177	−0.4349	0.089*
O1W	0.8353 (9)	0.6125 (7)	0.4395 (4)	0.115 (2)
H1W	0.825 (8)	0.619 (8)	0.382 (2)	0.10 (2)*
H2W	0.763 (10)	0.651 (12)	0.460 (5)	0.22 (6)*
I1	0.65018 (4)	0.84812 (3)	0.59621 (2)	0.05244 (12)
I2	0.88424 (4)	0.64775 (4)	0.20982 (3)	0.05905 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.044 (2)	0.037 (2)	0.037 (2)	0.0122 (16)	0.0147 (17)	0.0144 (15)
N2	0.043 (2)	0.0349 (19)	0.036 (2)	0.0050 (16)	0.0079 (17)	0.0144 (16)
N3	0.0349 (19)	0.0348 (18)	0.0307 (18)	0.0086 (15)	0.0034 (15)	0.0071 (14)
N4	0.045 (2)	0.044 (2)	0.035 (2)	0.0129 (17)	0.0108 (17)	0.0176 (16)
C1	0.038 (2)	0.038 (2)	0.032 (2)	0.0093 (18)	0.0156 (19)	0.0096 (17)
C2	0.044 (3)	0.039 (2)	0.043 (3)	0.005 (2)	0.013 (2)	0.017 (2)
C3	0.040 (3)	0.045 (3)	0.042 (3)	−0.003 (2)	0.013 (2)	0.011 (2)
C4	0.035 (2)	0.044 (2)	0.038 (2)	0.0119 (19)	0.015 (2)	0.0115 (19)
C5	0.047 (3)	0.039 (2)	0.036 (2)	0.016 (2)	0.017 (2)	0.0123 (19)
C6	0.059 (3)	0.033 (2)	0.051 (3)	0.016 (2)	0.025 (2)	0.020 (2)
C7	0.042 (3)	0.032 (2)	0.050 (3)	0.0036 (19)	0.013 (2)	0.0056 (19)
C8	0.039 (2)	0.037 (2)	0.035 (2)	0.0110 (18)	0.0113 (19)	0.0090 (18)
C9	0.034 (2)	0.036 (2)	0.033 (2)	0.0119 (17)	0.0155 (19)	0.0102 (17)
C10	0.031 (2)	0.037 (2)	0.035 (2)	0.0136 (17)	0.0151 (19)	0.0093 (17)
C11	0.040 (3)	0.037 (2)	0.043 (2)	0.0078 (19)	0.014 (2)	0.0163 (19)
C12	0.049 (3)	0.033 (2)	0.038 (2)	0.0104 (19)	0.012 (2)	0.0090 (18)
C13	0.063 (3)	0.034 (2)	0.060 (3)	0.018 (2)	0.022 (3)	0.015 (2)
C14	0.073 (4)	0.049 (3)	0.063 (3)	0.025 (3)	0.036 (3)	0.021 (2)
C15	0.070 (4)	0.049 (3)	0.044 (3)	0.003 (2)	0.022 (3)	0.015 (2)
C16	0.031 (2)	0.060 (3)	0.041 (3)	0.009 (2)	0.009 (2)	0.009 (2)
C17	0.037 (2)	0.036 (2)	0.042 (2)	0.0131 (18)	0.009 (2)	0.0109 (19)
C18	0.060 (3)	0.042 (3)	0.041 (3)	0.019 (2)	0.008 (2)	0.009 (2)
C19	0.049 (3)	0.034 (2)	0.043 (3)	0.0134 (19)	0.010 (2)	0.0147 (19)
C20	0.064 (3)	0.076 (4)	0.052 (3)	0.023 (3)	0.020 (3)	0.035 (3)
O1W	0.186 (6)	0.124 (4)	0.078 (4)	0.089 (4)	0.064 (4)	0.047 (3)
I1	0.0520 (2)	0.04436 (19)	0.0577 (2)	0.01444 (15)	0.01046 (16)	0.00959 (15)
I2	0.0690 (3)	0.0455 (2)	0.0787 (3)	0.02012 (16)	0.0281 (2)	0.03534 (17)

Geometric parameters (Å, º)

N1—C12	1.324 (5)	C7—C8	1.371 (6)
N1—C14	1.381 (6)	C7—H7	0.93
N1—C11	1.462 (5)	C8—C9	1.415 (6)
N2—C12	1.313 (5)	C8—H8	0.93
N2—C13	1.361 (6)	C9—C10	1.424 (6)
N2—C15	1.475 (5)	C11—H11A	0.97
N3—C17	1.314 (5)	C11—H11B	0.97
N3—C19	1.366 (5)	C12—H12	0.93
N3—C16	1.483 (5)	C13—C14	1.345 (7)
N4—C17	1.325 (5)	C13—H13	0.93
N4—C18	1.370 (5)	C14—H14	0.93
N4—C20	1.468 (6)	C15—H15A	0.96
C1—C2	1.368 (6)	C15—H15B	0.96
C1—C9	1.439 (5)	C15—H15C	0.96
C1—C11	1.501 (6)	C16—H16A	0.97
C2—C3	1.413 (6)	C16—H16B	0.97
C2—H2	0.93	C17—H17	0.93
C3—C4	1.368 (6)	C18—C19	1.335 (6)
C3—H3	0.93	C18—H18	0.93
C4—C10	1.431 (6)	C19—H19	0.93
C4—C16	1.510 (6)	C20—H20A	0.96
C5—C6	1.354 (6)	C20—H20B	0.96
C5—C10	1.415 (5)	C20—H20C	0.96
C5—H5	0.93	O1W—H1W	0.85 (4)
C6—C7	1.396 (6)	O1W—H2W	0.85 (9)
C6—H6	0.93
C12—N1—C14	107.5 (4)	N1—C11—H11A	108.6
C12—N1—C11	125.1 (4)	C1—C11—H11A	108.6
C14—N1—C11	127.3 (4)	N1—C11—H11B	108.6
C12—N2—C13	108.4 (4)	C1—C11—H11B	108.6
C12—N2—C15	126.2 (4)	H11A—C11—H11B	107.6
C13—N2—C15	125.4 (4)	N2—C12—N1	109.7 (4)
C17—N3—C19	108.5 (4)	N2—C12—H12	125.1
C17—N3—C16	126.1 (4)	N1—C12—H12	125.1
C19—N3—C16	125.4 (4)	C14—C13—N2	107.6 (4)
C17—N4—C18	108.3 (4)	C14—C13—H13	126.2
C17—N4—C20	125.5 (4)	N2—C13—H13	126.2
C18—N4—C20	126.1 (4)	C13—C14—N1	106.9 (4)
C2—C1—C9	118.9 (4)	C13—C14—H14	126.6
C2—C1—C11	122.9 (4)	N1—C14—H14	126.6
C9—C1—C11	118.2 (4)	N2—C15—H15A	109.5
C1—C2—C3	121.1 (4)	N2—C15—H15B	109.5
C1—C2—H2	119.5	H15A—C15—H15B	109.5
C3—C2—H2	119.5	N2—C15—H15C	109.5
C4—C3—C2	122.0 (4)	H15A—C15—H15C	109.5
C4—C3—H3	119.0	H15B—C15—H15C	109.5
C2—C3—H3	119.0	N3—C16—C4	111.6 (3)
C3—C4—C10	118.8 (4)	N3—C16—H16A	109.3
C3—C4—C16	119.9 (4)	C4—C16—H16A	109.3
C10—C4—C16	121.3 (4)	N3—C16—H16B	109.3
C6—C5—C10	121.7 (4)	C4—C16—H16B	109.3
C6—C5—H5	119.2	H16A—C16—H16B	108.0
C10—C5—H5	119.2	N3—C17—N4	108.7 (4)
C5—C6—C7	120.8 (4)	N3—C17—H17	125.6
C5—C6—H6	119.6	N4—C17—H17	125.6
C7—C6—H6	119.6	C19—C18—N4	106.9 (4)
C8—C7—C6	119.4 (4)	C19—C18—H18	126.5
C8—C7—H7	120.3	N4—C18—H18	126.5
C6—C7—H7	120.3	C18—C19—N3	107.5 (4)
C7—C8—C9	121.6 (4)	C18—C19—H19	126.2
C7—C8—H8	119.2	N3—C19—H19	126.2
C9—C8—H8	119.2	N4—C20—H20A	109.5
C8—C9—C10	118.4 (4)	N4—C20—H20B	109.5
C8—C9—C1	121.9 (4)	H20A—C20—H20B	109.5
C10—C9—C1	119.7 (4)	N4—C20—H20C	109.5
C5—C10—C9	118.1 (4)	H20A—C20—H20C	109.5
C5—C10—C4	122.3 (4)	H20B—C20—H20C	109.5
C9—C10—C4	119.6 (4)	H1W—O1W—H2W	107 (3)
N1—C11—C1	114.7 (3)
C9—C1—C2—C3	0.0 (6)	C14—N1—C11—C1	83.5 (6)
C11—C1—C2—C3	−179.3 (4)	C2—C1—C11—N1	−9.7 (6)
C1—C2—C3—C4	0.4 (7)	C9—C1—C11—N1	170.9 (4)
C2—C3—C4—C10	−1.1 (7)	C13—N2—C12—N1	0.2 (5)
C2—C3—C4—C16	179.0 (4)	C15—N2—C12—N1	179.0 (4)
C10—C5—C6—C7	0.2 (6)	C14—N1—C12—N2	−0.3 (5)
C5—C6—C7—C8	−0.5 (7)	C11—N1—C12—N2	−177.3 (4)
C6—C7—C8—C9	1.0 (6)	C12—N2—C13—C14	0.0 (6)
C7—C8—C9—C10	−1.1 (6)	C15—N2—C13—C14	−178.8 (4)
C7—C8—C9—C1	−178.8 (4)	N2—C13—C14—N1	−0.2 (6)
C2—C1—C9—C8	178.0 (4)	C12—N1—C14—C13	0.3 (6)
C11—C1—C9—C8	−2.6 (6)	C11—N1—C14—C13	177.2 (4)
C2—C1—C9—C10	0.3 (6)	C17—N3—C16—C4	−118.7 (5)
C11—C1—C9—C10	179.7 (4)	C19—N3—C16—C4	64.8 (5)
C6—C5—C10—C9	−0.3 (6)	C3—C4—C16—N3	−100.6 (5)
C6—C5—C10—C4	179.1 (4)	C10—C4—C16—N3	79.6 (5)
C8—C9—C10—C5	0.7 (5)	C19—N3—C17—N4	−1.1 (5)
C1—C9—C10—C5	178.5 (4)	C16—N3—C17—N4	−178.2 (4)
C8—C9—C10—C4	−178.8 (4)	C18—N4—C17—N3	1.7 (5)
C1—C9—C10—C4	−1.0 (6)	C20—N4—C17—N3	179.1 (4)
C3—C4—C10—C5	−178.1 (4)	C17—N4—C18—C19	−1.6 (5)
C16—C4—C10—C5	1.8 (6)	C20—N4—C18—C19	−179.0 (4)
C3—C4—C10—C9	1.4 (6)	N4—C18—C19—N3	0.9 (5)
C16—C4—C10—C9	−178.8 (4)	C17—N3—C19—C18	0.2 (5)
C12—N1—C11—C1	−100.2 (5)	C16—N3—C19—C18	177.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···I2	0.85 (4)	2.76 (4)	3.578 (6)	164 (6)
O1W—H2W···I1	0.85 (9)	2.87 (9)	3.649 (7)	154 (6)
C17—H17···I2^i	0.93	2.90	3.799 (5)	162
C18—H18···O1W^ii	0.93	2.52	3.327 (8)	145
C19—H19···I2^ii	0.93	2.93	3.830 (4)	163

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