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The title compound, C16H25N3O2+·2I, was synthesized from 1-(2-morpholinoethyl)­benz­imidazole and iso­propyl iodide in tetra­hydro­furan. In the mol­ecule, the benz­imidazole ring is connected to the morpholine ring by an ethyl­ene group. The crystal structure has been determined at 150 K and exhibits intermolecular C—H...I interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026637/fl6128sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026637/fl6128Isup2.hkl
Contains datablock I

CCDC reference: 255941

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.020
  • wR factor = 0.045
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.19 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 18 PLAT432_ALERT_2_C Short Inter X...Y Contact I1 .. C13 .. 3.43 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Isopropyl-3-(2-morpholinioethyl)benzimidazolium diiodide top
Crystal data top
C16H25N3O2+·2IF(000) = 1024
Mr = 529.19Dx = 1.754 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4269 reflections
a = 12.078 (5) Åθ = 1.7–27.2°
b = 19.923 (5) ŵ = 3.14 mm1
c = 8.336 (5) ÅT = 150 K
β = 92.537 (5)°Block, colorless
V = 2003.9 (15) Å30.40 × 0.36 × 0.30 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
4269 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3736 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.032
Detector resolution: 6.67 pixels mm-1θmax = 27.1°, θmin = 2.0°
ω scansh = 1515
Absorption correction: integration
STOE X-RED32 (Stoe & Cie, 2002)
k = 2525
Tmin = 0.366, Tmax = 0.452l = 1010
14805 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.045 w = 1/[σ2(Fo2) + (0.0287P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4269 reflectionsΔρmax = 0.54 e Å3
276 parametersΔρmin = 0.77 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00223 (16)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O11.08911 (13)0.19917 (8)0.85099 (19)0.0333 (5)
N10.92509 (13)0.13198 (9)0.6492 (2)0.0223 (5)
N20.66478 (14)0.10439 (9)0.3901 (2)0.0248 (5)
N30.48874 (13)0.11091 (9)0.3202 (2)0.0260 (5)
C10.95631 (18)0.10855 (11)0.8160 (3)0.0271 (6)
C21.07479 (18)0.12842 (12)0.8591 (3)0.0302 (7)
C31.0652 (2)0.22163 (12)0.6920 (3)0.0342 (7)
C40.94679 (19)0.20618 (11)0.6364 (3)0.0294 (6)
C50.80723 (16)0.11333 (11)0.6050 (3)0.0254 (6)
C60.77788 (16)0.12709 (12)0.4295 (3)0.0264 (6)
C70.63052 (17)0.03957 (11)0.3528 (3)0.0267 (6)
C80.6884 (2)0.02078 (12)0.3553 (3)0.0319 (7)
C90.6274 (2)0.07697 (12)0.3112 (3)0.0384 (8)
C100.5142 (2)0.07342 (13)0.2667 (3)0.0385 (8)
C110.4573 (2)0.01326 (12)0.2637 (3)0.0338 (7)
C120.51859 (17)0.04349 (11)0.3085 (3)0.0274 (6)
C130.57840 (16)0.14541 (12)0.3662 (3)0.0261 (6)
C140.37708 (17)0.13890 (12)0.2775 (3)0.0314 (7)
C150.3569 (2)0.13651 (15)0.0973 (3)0.0416 (8)
C160.3669 (2)0.20879 (14)0.3457 (4)0.0447 (8)
I10.68452 (1)0.18706 (1)0.00486 (2)0.0289 (1)
I20.92209 (1)0.07790 (1)0.66984 (2)0.0293 (1)
H10.971 (2)0.1093 (14)0.577 (4)0.044 (7)*
H1A0.906 (2)0.1313 (13)0.888 (3)0.037 (7)*
H1B0.945 (2)0.0588 (14)0.817 (3)0.036 (7)*
H2A1.091 (2)0.1162 (13)0.958 (4)0.034 (7)*
H2B1.123 (2)0.1066 (13)0.787 (3)0.034 (7)*
H3A1.072 (2)0.2704 (13)0.694 (3)0.033 (6)*
H3B1.117 (2)0.2030 (14)0.616 (4)0.046 (8)*
H4A0.892 (2)0.2262 (12)0.704 (3)0.031 (6)*
H4B0.936 (2)0.2144 (12)0.528 (3)0.030 (6)*
H5A0.7634 (19)0.1407 (11)0.676 (3)0.025 (6)*
H5B0.804 (2)0.0637 (15)0.630 (4)0.049 (8)*
H6A0.7807 (18)0.1741 (11)0.405 (3)0.016 (5)*
H6B0.824 (2)0.1001 (13)0.364 (3)0.031 (6)*
H80.765 (2)0.0215 (11)0.389 (3)0.024 (6)*
H90.667 (2)0.1179 (14)0.306 (3)0.040 (7)*
H100.475 (3)0.1117 (17)0.232 (4)0.059 (9)*
H110.384 (2)0.0104 (12)0.235 (3)0.031 (6)*
H130.5779 (19)0.1871 (12)0.389 (3)0.020 (6)*
H140.327 (2)0.1093 (13)0.321 (3)0.031 (6)*
H15A0.364300.091100.060600.0620*
H15B0.410100.164500.047100.0620*
H15C0.283500.152400.069900.0620*
H16A0.380400.207400.460000.0670*
H16B0.293600.225700.321400.0670*
H16C0.420200.237700.298900.0670*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0337 (8)0.0372 (8)0.0280 (8)0.0085 (7)0.0084 (7)0.0033 (7)
N10.0170 (8)0.0284 (9)0.0214 (8)0.0010 (6)0.0008 (7)0.0012 (7)
N20.0182 (8)0.0314 (9)0.0244 (9)0.0028 (7)0.0018 (7)0.0014 (7)
N30.0166 (8)0.0364 (9)0.0249 (9)0.0031 (7)0.0011 (7)0.0018 (7)
C10.0261 (10)0.0313 (11)0.0234 (10)0.0007 (9)0.0031 (8)0.0008 (9)
C20.0267 (11)0.0377 (12)0.0255 (11)0.0001 (9)0.0065 (9)0.0003 (10)
C30.0314 (12)0.0378 (13)0.0326 (12)0.0106 (10)0.0067 (10)0.0010 (10)
C40.0275 (11)0.0269 (10)0.0332 (12)0.0030 (8)0.0068 (9)0.0027 (9)
C50.0173 (9)0.0319 (11)0.0267 (10)0.0037 (8)0.0009 (8)0.0033 (9)
C60.0156 (9)0.0376 (12)0.0257 (10)0.0034 (8)0.0022 (8)0.0010 (9)
C70.0238 (10)0.0345 (11)0.0216 (10)0.0032 (8)0.0006 (8)0.0033 (8)
C80.0284 (11)0.0393 (12)0.0278 (11)0.0006 (9)0.0007 (9)0.0037 (9)
C90.0464 (15)0.0340 (12)0.0349 (13)0.0001 (10)0.0033 (11)0.0074 (10)
C100.0454 (14)0.0393 (13)0.0307 (12)0.0135 (11)0.0013 (11)0.0094 (10)
C110.0297 (12)0.0441 (13)0.0273 (11)0.0111 (10)0.0006 (9)0.0029 (10)
C120.0225 (10)0.0354 (11)0.0240 (10)0.0044 (8)0.0008 (8)0.0010 (9)
C130.0189 (9)0.0317 (11)0.0273 (11)0.0016 (8)0.0017 (8)0.0000 (9)
C140.0139 (9)0.0451 (13)0.0348 (12)0.0024 (9)0.0026 (8)0.0046 (10)
C150.0255 (11)0.0653 (17)0.0331 (13)0.0019 (11)0.0079 (10)0.0098 (12)
C160.0267 (12)0.0520 (15)0.0547 (16)0.0092 (11)0.0062 (11)0.0001 (13)
I10.0243 (1)0.0355 (1)0.0270 (1)0.0023 (1)0.0020 (1)0.0001 (1)
I20.0219 (1)0.0375 (1)0.0288 (1)0.0015 (1)0.0046 (1)0.0006 (1)
Geometric parameters (Å, º) top
O1—C21.422 (3)C1—H1B1.00 (3)
O1—C31.416 (3)C2—H2A0.87 (3)
N1—C11.499 (3)C2—H2B0.96 (2)
N1—C41.506 (3)C3—H3A0.98 (3)
N1—C51.501 (3)C3—H3B0.98 (3)
N2—C61.462 (3)C4—H4A0.97 (2)
N2—C71.387 (3)C4—H4B0.92 (3)
N2—C131.333 (3)C5—H5A0.98 (2)
N3—C121.395 (3)C5—H5B1.01 (3)
N3—C131.325 (3)C6—H6A0.96 (2)
N3—C141.488 (3)C6—H6B0.96 (2)
N1—H10.95 (3)C8—H80.96 (2)
C1—C21.513 (3)C9—H90.95 (3)
C3—C41.515 (3)C10—H100.94 (3)
C5—C61.515 (4)C11—H110.91 (2)
C7—C81.391 (3)C13—H130.85 (2)
C7—C121.388 (3)C14—H140.93 (2)
C8—C91.381 (4)C15—H15A0.9600
C9—C101.403 (4)C15—H15B0.9600
C10—C111.381 (4)C15—H15C0.9600
C11—C121.393 (3)C16—H16A0.9600
C14—C151.512 (4)C16—H16B0.9600
C14—C161.511 (4)C16—H16C0.9600
C1—H1A0.98 (3)
I1···N23.626 (3)H1A···H4A2.44 (4)
I1···C63.857 (3)H1B···H5B2.26 (4)
I1···C133.427 (3)H1B···I23.00 (3)
I1···C13i3.740 (3)H2A···H15Cx2.5700
I2···C14ii3.856 (3)H2A···I2vii3.21 (3)
I2···N1iii3.475 (3)H2B···H12.48 (4)
I2···C6iii3.879 (3)H2B···H3B2.39 (4)
I1···H5Aiv3.08 (2)H3A···I2xii3.23 (3)
I1···H15B3.3800H3B···H2B2.39 (4)
I1···H1Aiv3.09 (2)H3B···H12.58 (4)
I1···H13i2.96 (2)H4A···H1A2.44 (4)
I1···H10v3.09 (3)H4A···H5A2.31 (3)
I1···H6Ai3.13 (2)H4B···H6A2.25 (3)
I2···H3Avi3.23 (3)H4B···C62.69 (2)
I2···H83.15 (2)H5A···H4A2.31 (3)
I2···H5B3.17 (3)H5A···H1A2.42 (3)
I2···H1B3.00 (3)H5A···I1xi3.08 (2)
I2···H1iii2.56 (3)H5B···H1B2.26 (4)
I2···H6Biii3.12 (2)H5B···I23.17 (3)
I2···H14ii3.08 (2)H5B···C73.09 (3)
I2···H2Avii3.21 (3)H6A···C42.80 (2)
O1···C3viii3.275 (4)H6A···I1viii3.13 (2)
O1···N12.872 (3)H6A···H4B2.25 (3)
O1···H16Bix2.9100H6A···H132.46 (3)
N1···O12.872 (3)H6B···I2iii3.12 (2)
N1···I2iii3.475 (3)H6B···C82.91 (3)
N2···I13.626 (3)H6B···H12.46 (4)
N2···N32.184 (3)H6B···H82.54 (3)
N3···N22.184 (3)H8···I23.15 (2)
C3···O1i3.275 (4)H8···C62.98 (2)
C6···I13.857 (3)H8···H6B2.54 (3)
C6···I2iii3.879 (3)H10···I1v3.09 (3)
C7···C11ii3.453 (4)H11···H15A2.5000
C11···C153.486 (4)H11···H142.59 (4)
C11···C7ii3.453 (4)H11···C143.00 (2)
C13···I1viii3.740 (3)H13···C162.59 (2)
C13···I13.427 (3)H13···H16A2.5200
C14···I2ii3.856 (3)H13···H16C2.2500
C15···C113.486 (4)H13···H6A2.46 (3)
C2···H15Cx3.0500H13···I1viii2.96 (2)
C4···H6A2.80 (2)H14···H112.59 (4)
C6···H4B2.69 (2)H14···I2ii3.08 (2)
C6···H82.98 (2)H14···C112.96 (3)
C7···H5B3.09 (3)H15A···C112.8800
C8···H6B2.91 (3)H15A···C122.8800
C11···H142.96 (3)H15A···H112.5000
C11···H15A2.8800H15B···C16i3.0600
C12···H15A2.8800H15B···H16C2.5500
C13···H16C2.6900H15B···I13.3800
C13···H16A2.8300H15C···H16B2.5500
C14···H113.00 (2)H15C···H2Axiii2.5700
C16···H132.59 (2)H15C···C2xiii3.0500
C16···H15Bviii3.0600H16A···C132.8300
H1···H3B2.58 (4)H16A···H132.5200
H1···H2B2.48 (4)H16B···H15C2.5500
H1···H6B2.46 (4)H16B···O1xiv2.9100
H1···I2iii2.56 (3)H16C···H15B2.5500
H1A···H5A2.42 (3)H16C···C132.6900
H1A···I1xi3.09 (2)H16C···H132.2500
C2—O1—C3109.72 (17)O1—C3—H3B112.0 (18)
C1—N1—C4109.51 (17)C4—C3—H3A106.6 (14)
C1—N1—C5110.33 (16)C4—C3—H3B110.2 (16)
C4—N1—C5113.06 (16)H3A—C3—H3B109 (2)
C6—N2—C7127.20 (18)N1—C4—H4A103.7 (14)
C6—N2—C13124.12 (19)N1—C4—H4B103.1 (15)
C7—N2—C13108.27 (17)C3—C4—H4A113.4 (15)
C12—N3—C13108.01 (17)C3—C4—H4B110.8 (15)
C12—N3—C14125.33 (17)H4A—C4—H4B115 (2)
C13—N3—C14126.54 (19)N1—C5—H5A104.3 (14)
C5—N1—H1107.5 (16)N1—C5—H5B103.7 (14)
C1—N1—H1108.0 (19)C6—C5—H5A112.0 (14)
C4—N1—H1108.3 (17)C6—C5—H5B111.5 (19)
N1—C1—C2109.59 (18)H5A—C5—H5B113 (2)
O1—C2—C1111.34 (18)N2—C6—H6A107.2 (13)
O1—C3—C4111.88 (19)N2—C6—H6B105.0 (15)
N1—C4—C3110.04 (18)C5—C6—H6A111.9 (15)
N1—C5—C6111.78 (17)C5—C6—H6B109.3 (15)
N2—C6—C5109.71 (17)H6A—C6—H6B114 (2)
C8—C7—C12122.4 (2)C7—C8—H8119.8 (13)
N2—C7—C12106.54 (18)C9—C8—H8124.4 (13)
N2—C7—C8131.1 (2)C8—C9—H9116.5 (15)
C7—C8—C9115.8 (2)C10—C9—H9121.3 (15)
C8—C9—C10122.1 (2)C9—C10—H10121 (2)
C9—C10—C11121.8 (2)C11—C10—H10117 (2)
C10—C11—C12116.2 (2)C10—C11—H11122.5 (15)
C7—C12—C11121.7 (2)C12—C11—H11121.3 (15)
N3—C12—C7106.69 (18)N2—C13—H13125.3 (16)
N3—C12—C11131.6 (2)N3—C13—H13123.8 (16)
N2—C13—N3110.5 (2)N3—C14—H14105.5 (16)
N3—C14—C15109.30 (18)C15—C14—H14106.8 (15)
N3—C14—C16110.08 (19)C16—C14—H14111.9 (16)
C15—C14—C16113.0 (2)C14—C15—H15A109.00
N1—C1—H1A106.6 (15)C14—C15—H15B109.00
N1—C1—H1B106.7 (14)C14—C15—H15C109.00
C2—C1—H1A109.8 (15)H15A—C15—H15B110.00
C2—C1—H1B112.7 (14)H15A—C15—H15C109.00
H1A—C1—H1B111 (2)H15B—C15—H15C109.00
O1—C2—H2A107.4 (17)C14—C16—H16A109.00
O1—C2—H2B109.9 (16)C14—C16—H16B109.00
C1—C2—H2A108.8 (16)C14—C16—H16C109.00
C1—C2—H2B109.1 (15)H16A—C16—H16B110.00
H2A—C2—H2B110 (2)H16A—C16—H16C109.00
O1—C3—H3A106.6 (15)H16B—C16—H16C109.00
C3—O1—C2—C161.8 (2)C13—N3—C12—C71.0 (3)
C2—O1—C3—C460.7 (2)C14—N3—C12—C112.8 (4)
C4—N1—C1—C254.3 (2)C12—N3—C13—N21.9 (3)
C1—N1—C4—C353.2 (2)C14—N3—C13—N2178.10 (19)
C5—N1—C1—C2179.39 (17)C14—N3—C12—C7177.3 (2)
C5—N1—C4—C3176.69 (19)C13—N3—C12—C11179.1 (3)
C1—N1—C5—C6171.71 (18)N1—C1—C2—O159.3 (2)
C4—N1—C5—C665.3 (2)O1—C3—C4—N157.0 (2)
C7—N2—C13—N31.9 (3)N1—C5—C6—N2176.58 (17)
C7—N2—C6—C582.3 (3)N2—C7—C12—N30.1 (3)
C6—N2—C7—C86.2 (4)C8—C7—C12—N3179.9 (2)
C6—N2—C7—C12174.1 (2)C8—C7—C12—C110.0 (4)
C13—N2—C7—C121.2 (3)C12—C7—C8—C90.2 (4)
C13—N2—C7—C8179.0 (3)N2—C7—C8—C9179.6 (2)
C6—N2—C13—N3175.07 (19)N2—C7—C12—C11179.8 (2)
C13—N2—C6—C5106.0 (2)C7—C8—C9—C100.0 (4)
C12—N3—C14—C1570.3 (3)C8—C9—C10—C110.3 (4)
C13—N3—C14—C1619.3 (3)C9—C10—C11—C120.5 (4)
C13—N3—C14—C15105.4 (3)C10—C11—C12—C70.3 (4)
C12—N3—C14—C16165.1 (2)C10—C11—C12—N3179.6 (2)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y, z+1; (iii) x+2, y, z+1; (iv) x, y, z1; (v) x+1, y, z; (vi) x+2, y1/2, z+3/2; (vii) x+2, y, z+2; (viii) x, y+1/2, z+1/2; (ix) x+1, y+1/2, z+1/2; (x) x+1, y, z+1; (xi) x, y, z+1; (xii) x+2, y+1/2, z+3/2; (xiii) x1, y, z1; (xiv) x1, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···I2iii0.95 (3)2.56 (3)3.475 (3)163 (2)
C1—H1B···I21.00 (3)3.00 (3)3.926 (3)155.2 (19)
C13—H13···I1viii0.85 (2)2.96 (2)3.740 (3)153.0 (19)
Symmetry codes: (iii) x+2, y, z+1; (viii) x, y+1/2, z+1/2.
 

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