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The title compound, C22H26I2N4, (I), was synthesized by reaction of 1,4-bis­(imidazoly­methyl)­naphthalene with iodo­ethane. The X-ray structure of (I) reveals the presence of discrete hydrogen-bond interactions and π–π-stacking interactions of naphthalene rings, resulting in a three-dimensional structure. A methanol solvent mol­ecule is also found in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016933/ww6102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016933/ww6102Isup2.hkl
Contains datablock I

CCDC reference: 225704

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.068
  • wR factor = 0.184
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.41 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C2 = 5.52 su PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15 PLAT731_ALERT_1_C Bond Calc 1.52(2), Rep 1.523(9) ...... 2.22 su-Rat C1 -C2 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3,3'-(1,4-Naphthalenedimethylene)bis(1-ethylimidazolium) diiodide methanol solvate top
Crystal data top
C22H26N42+·2I·CH4OZ = 2
Mr = 632.31F(000) = 620
Triclinic, P1Dx = 1.606 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.959 (5) ÅCell parameters from 715 reflections
b = 10.770 (5) Åθ = 3.1–22.8°
c = 13.407 (7) ŵ = 2.43 mm1
α = 98.340 (11)°T = 293 K
β = 104.132 (12)°Block, yellow
γ = 105.691 (12)°0.20 × 0.18 × 0.14 mm
V = 1307.7 (11) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4417 independent reflections
Radiation source: fine-focus sealed tube2512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.608, Tmax = 0.712k = 1212
6446 measured reflectionsl = 158
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0555P)2]
where P = (Fo2 + 2Fc2)/3
4417 reflections(Δ/σ)max = 0.001
276 parametersΔρmax = 1.73 e Å3
241 restraintsΔρmin = 0.75 e Å3
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
xyzUiso*/Ueq
I10.16861 (7)0.81874 (7)0.57397 (6)0.0686 (3)
I20.62724 (10)0.49949 (8)0.84818 (7)0.0893 (3)
N10.8550 (11)0.6547 (8)1.1925 (7)0.072 (2)
N20.7439 (8)0.7999 (7)1.1957 (6)0.0537 (19)
N30.6662 (8)0.8846 (7)0.6809 (6)0.0504 (18)
N40.7472 (8)0.7349 (8)0.6179 (7)0.060 (2)
C10.849 (2)0.4420 (16)1.2211 (15)0.144 (6)
H1A0.92510.45651.28550.215*
H1B0.82400.35301.18140.215*
H1C0.76450.45541.23720.215*
C20.9020 (18)0.5389 (14)1.1561 (13)0.111 (4)
H2A1.00730.56441.17090.134*
H2B0.85630.50141.08100.134*
C30.9239 (14)0.7481 (12)1.2874 (10)0.082 (3)
H31.00430.74781.34000.099*
C40.8564 (13)0.8361 (11)1.2899 (9)0.076 (3)
H40.87930.90951.34450.092*
C50.7455 (11)0.6897 (10)1.1401 (8)0.061 (3)
H50.68010.64371.07440.073*
C60.6363 (10)0.8686 (9)1.1628 (8)0.053 (2)
H6A0.66360.95201.21320.064*
H6B0.54090.81491.16300.064*
C70.6272 (9)0.8944 (9)1.0544 (8)0.0498 (18)
C80.7456 (9)0.9917 (8)1.0357 (7)0.0461 (17)
C90.8724 (9)1.0718 (9)1.1193 (8)0.052 (2)
H90.88051.06251.18820.063*
C100.9804 (11)1.1606 (10)1.0990 (9)0.061 (2)
H101.06391.21071.15370.073*
C110.9679 (11)1.1780 (10)0.9961 (8)0.061 (2)
H111.04241.24070.98300.074*
C120.8461 (11)1.1030 (9)0.9143 (9)0.062 (2)
H120.84031.11550.84630.075*
C130.7329 (9)1.0104 (9)0.9299 (7)0.0486 (18)
C140.6028 (9)0.9339 (9)0.8482 (7)0.0503 (19)
C150.4910 (10)0.8454 (9)0.8687 (8)0.056 (2)
H150.40570.79800.81460.067*
C160.5061 (10)0.8266 (10)0.9715 (8)0.056 (2)
H160.42980.76500.98380.067*
C170.5816 (10)0.9496 (10)0.7354 (8)0.056 (2)
H17A0.47870.91190.69640.068*
H17B0.61141.04310.73550.068*
C180.7447 (11)0.9366 (11)0.6173 (9)0.069 (3)
H180.76021.02120.60470.083*
C190.7944 (11)0.8452 (11)0.5772 (9)0.068 (3)
H190.85030.85290.53070.081*
C200.6700 (10)0.7636 (9)0.6802 (8)0.054 (2)
H200.62560.70720.71740.065*
C210.7810 (13)0.6104 (11)0.5969 (10)0.079 (3)
H21A0.74570.55430.64160.094*
H21B0.88610.63000.61500.094*
C220.7126 (19)0.5368 (16)0.4828 (14)0.123 (5)
H22A0.61740.54520.45720.184*
H22B0.70400.44490.47730.184*
H22C0.77290.57340.44150.184*
C230.4375 (18)0.7814 (16)0.3996 (14)0.125 (5)
H23A0.52120.82840.38100.188*
H23B0.44910.70060.41660.188*
H23C0.42860.83540.45970.188*
O10.3075 (13)0.7512 (12)0.3115 (9)0.124 (3)
H10.31390.70300.26080.185*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0571 (4)0.0788 (5)0.0573 (4)0.0159 (3)0.0053 (3)0.0082 (3)
I20.1182 (7)0.0630 (5)0.0769 (6)0.0082 (4)0.0337 (5)0.0173 (4)
N10.096 (6)0.059 (5)0.058 (5)0.041 (5)0.002 (5)0.012 (5)
N20.063 (5)0.048 (5)0.053 (5)0.019 (4)0.017 (4)0.020 (4)
N30.048 (4)0.051 (5)0.044 (4)0.015 (4)0.002 (4)0.006 (4)
N40.051 (4)0.065 (5)0.064 (5)0.021 (4)0.017 (4)0.012 (4)
C10.158 (9)0.120 (8)0.148 (9)0.039 (7)0.042 (7)0.031 (7)
C20.127 (8)0.105 (7)0.104 (8)0.048 (6)0.021 (6)0.031 (6)
C30.092 (6)0.074 (6)0.069 (5)0.026 (5)0.001 (5)0.020 (5)
C40.087 (6)0.068 (5)0.065 (5)0.025 (5)0.006 (5)0.014 (5)
C50.074 (6)0.052 (5)0.054 (5)0.021 (4)0.010 (5)0.020 (4)
C60.056 (4)0.051 (4)0.056 (4)0.020 (4)0.021 (4)0.009 (4)
C70.045 (3)0.050 (4)0.057 (4)0.015 (3)0.021 (3)0.010 (3)
C80.045 (3)0.046 (3)0.052 (4)0.023 (3)0.015 (3)0.011 (3)
C90.049 (4)0.054 (4)0.052 (4)0.018 (3)0.008 (3)0.015 (3)
C100.051 (4)0.062 (4)0.062 (4)0.009 (4)0.014 (4)0.010 (4)
C110.052 (4)0.062 (4)0.065 (4)0.009 (4)0.015 (4)0.020 (4)
C120.062 (4)0.059 (4)0.064 (4)0.013 (4)0.018 (4)0.019 (4)
C130.043 (3)0.050 (4)0.056 (4)0.020 (3)0.015 (3)0.013 (3)
C140.046 (3)0.051 (4)0.055 (4)0.018 (3)0.013 (3)0.015 (3)
C150.042 (4)0.062 (4)0.060 (4)0.016 (3)0.010 (3)0.011 (4)
C160.045 (4)0.055 (4)0.062 (4)0.008 (3)0.014 (4)0.014 (4)
C170.049 (4)0.065 (5)0.054 (4)0.020 (4)0.014 (4)0.011 (4)
C180.065 (5)0.070 (5)0.073 (5)0.018 (4)0.021 (4)0.027 (5)
C190.066 (5)0.072 (5)0.071 (5)0.019 (4)0.029 (4)0.026 (5)
C200.050 (5)0.057 (5)0.059 (5)0.017 (4)0.017 (4)0.025 (4)
C210.082 (6)0.078 (6)0.084 (6)0.032 (5)0.029 (5)0.024 (5)
C220.132 (8)0.114 (8)0.121 (8)0.052 (6)0.026 (7)0.015 (7)
C230.132 (9)0.127 (9)0.112 (9)0.049 (7)0.017 (7)0.030 (7)
O10.132 (8)0.115 (9)0.106 (8)0.046 (7)0.002 (7)0.015 (7)
Geometric parameters (Å, º) top
N1—C51.322 (12)C9—H90.9300
N1—C31.389 (15)C10—C111.400 (14)
N1—C21.505 (16)C10—H100.9300
N2—C51.312 (12)C11—C121.375 (14)
N2—C41.391 (14)C11—H110.9300
N2—C61.478 (11)C12—C131.370 (12)
N3—C201.313 (11)C12—H120.9300
N3—C181.371 (12)C13—C141.423 (13)
N3—C171.484 (11)C14—C151.369 (12)
N4—C201.323 (12)C14—C171.517 (13)
N4—C191.393 (13)C15—C161.400 (14)
N4—C211.473 (14)C15—H150.9300
C1—C21.523 (9)C16—H160.9300
C1—H1A0.9600C17—H17A0.9700
C1—H1B0.9600C17—H17B0.9700
C1—H1C0.9600C18—C191.321 (15)
C2—H2A0.9700C18—H180.9300
C2—H2B0.9700C19—H190.9300
C3—C41.304 (16)C20—H200.9300
C3—H30.9300C21—C221.51 (2)
C4—H40.9300C21—H21A0.9700
C5—H50.9300C21—H21B0.9700
C6—C71.504 (13)C22—H22A0.9600
C6—H6A0.9700C22—H22B0.9600
C6—H6B0.9700C22—H22C0.9600
C7—C161.363 (13)C23—O11.446 (17)
C7—C81.451 (12)C23—H23A0.9600
C8—C91.427 (13)C23—H23B0.9600
C8—C131.440 (13)C23—H23C0.9600
C9—C101.344 (12)O1—H10.8200
C5—N1—C3107.3 (9)C12—C11—H11119.8
C5—N1—C2127.2 (11)C10—C11—H11119.8
C3—N1—C2125.4 (11)C13—C12—C11121.9 (10)
C5—N2—C4108.2 (8)C13—C12—H12119.1
C5—N2—C6124.7 (9)C11—C12—H12119.1
C4—N2—C6127.1 (9)C12—C13—C14123.7 (9)
C20—N3—C18108.5 (8)C12—C13—C8117.9 (9)
C20—N3—C17125.3 (8)C14—C13—C8118.3 (8)
C18—N3—C17126.1 (8)C15—C14—C13121.4 (9)
C20—N4—C19107.6 (8)C15—C14—C17117.5 (9)
C20—N4—C21126.6 (9)C13—C14—C17121.1 (8)
C19—N4—C21125.8 (9)C14—C15—C16119.5 (9)
C2—C1—H1A109.5C14—C15—H15120.2
C2—C1—H1B109.5C16—C15—H15120.2
H1A—C1—H1B109.5C7—C16—C15123.1 (9)
C2—C1—H1C109.5C7—C16—H16118.5
H1A—C1—H1C109.5C15—C16—H16118.5
H1B—C1—H1C109.5N3—C17—C14112.7 (7)
N1—C2—C1102.7 (12)N3—C17—H17A109.1
N1—C2—H2A111.2C14—C17—H17A109.1
C1—C2—H2A111.2N3—C17—H17B109.1
N1—C2—H2B111.2C14—C17—H17B109.1
C1—C2—H2B111.2H17A—C17—H17B107.8
H2A—C2—H2B109.1C19—C18—N3107.9 (9)
C4—C3—N1108.2 (11)C19—C18—H18126.1
C4—C3—H3125.9N3—C18—H18126.1
N1—C3—H3125.9C18—C19—N4107.0 (9)
C3—C4—N2107.1 (11)C18—C19—H19126.5
C3—C4—H4126.4N4—C19—H19126.5
N2—C4—H4126.4N3—C20—N4109.1 (8)
N2—C5—N1109.1 (9)N3—C20—H20125.5
N2—C5—H5125.4N4—C20—H20125.5
N1—C5—H5125.4N4—C21—C22112.1 (11)
N2—C6—C7111.8 (7)N4—C21—H21A109.2
N2—C6—H6A109.3C22—C21—H21A109.2
C7—C6—H6A109.3N4—C21—H21B109.2
N2—C6—H6B109.3C22—C21—H21B109.2
C7—C6—H6B109.3H21A—C21—H21B107.9
H6A—C6—H6B107.9C21—C22—H22A109.5
C16—C7—C8118.5 (9)C21—C22—H22B109.5
C16—C7—C6120.2 (8)H22A—C22—H22B109.5
C8—C7—C6121.2 (9)C21—C22—H22C109.5
C9—C8—C13119.1 (8)H22A—C22—H22C109.5
C9—C8—C7121.9 (8)H22B—C22—H22C109.5
C13—C8—C7119.0 (8)O1—C23—H23A109.5
C10—C9—C8120.3 (9)O1—C23—H23B109.5
C10—C9—H9119.8H23A—C23—H23B109.5
C8—C9—H9119.8O1—C23—H23C109.5
C9—C10—C11120.4 (10)H23A—C23—H23C109.5
C9—C10—H10119.8H23B—C23—H23C109.5
C11—C10—H10119.8C23—O1—H1109.5
C12—C11—C10120.4 (9)
C5—N1—C2—C1105.9 (14)C7—C8—C13—C12179.9 (8)
C3—N1—C2—C176.7 (17)C9—C8—C13—C14177.2 (8)
C5—N1—C3—C40.4 (14)C7—C8—C13—C141.2 (12)
C2—N1—C3—C4177.5 (11)C12—C13—C14—C15178.0 (9)
N1—C3—C4—N20.4 (13)C8—C13—C14—C150.6 (13)
C5—N2—C4—C31.1 (12)C12—C13—C14—C170.8 (14)
C6—N2—C4—C3179.3 (9)C8—C13—C14—C17179.4 (7)
C4—N2—C5—N11.3 (11)C13—C14—C15—C161.7 (14)
C6—N2—C5—N1179.6 (8)C17—C14—C15—C16179.4 (9)
C3—N1—C5—N21.1 (12)C8—C7—C16—C150.7 (14)
C2—N1—C5—N2176.7 (10)C6—C7—C16—C15179.6 (9)
C5—N2—C6—C753.0 (11)C14—C15—C16—C71.1 (15)
C4—N2—C6—C7129.1 (10)C20—N3—C17—C1447.9 (12)
N2—C6—C7—C16109.8 (10)C18—N3—C17—C14136.9 (9)
N2—C6—C7—C870.5 (10)C15—C14—C17—N3105.0 (9)
C16—C7—C8—C9176.5 (8)C13—C14—C17—N376.2 (11)
C6—C7—C8—C93.2 (13)C20—N3—C18—C190.7 (11)
C16—C7—C8—C131.8 (12)C17—N3—C18—C19175.1 (9)
C6—C7—C8—C13178.5 (8)N3—C18—C19—N40.7 (12)
C13—C8—C9—C102.0 (13)C20—N4—C19—C180.5 (12)
C7—C8—C9—C10179.7 (8)C21—N4—C19—C18178.1 (11)
C8—C9—C10—C111.7 (14)C18—N3—C20—N40.4 (10)
C9—C10—C11—C121.0 (16)C17—N3—C20—N4175.4 (8)
C10—C11—C12—C130.6 (16)C19—N4—C20—N30.0 (11)
C11—C12—C13—C14177.7 (9)C21—N4—C20—N3178.5 (10)
C11—C12—C13—C80.9 (14)C20—N4—C21—C22115.6 (13)
C9—C8—C13—C121.5 (12)C19—N4—C21—C2266.1 (16)
 

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