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The title compound, C
16H
25N
3O
2+·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
CCDC reference: 255941
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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+·2I− | F(000) = 1024 |
Mr = 529.19 | Dx = 1.754 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4269 reflections |
a = 12.078 (5) Å | θ = 1.7–27.2° |
b = 19.923 (5) Å | µ = 3.14 mm−1 |
c = 8.336 (5) Å | T = 150 K |
β = 92.537 (5)° | Block, colorless |
V = 2003.9 (15) Å3 | 0.40 × 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 focus | 3736 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.032 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.1°, θmin = 2.0° |
ω scans | h = −15→15 |
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002) | k = −25→25 |
Tmin = 0.366, Tmax = 0.452 | l = −10→10 |
14805 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H 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 reflections | Δρmax = 0.54 e Å−3 |
276 parameters | Δρmin = −0.77 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 1.08911 (13) | 0.19917 (8) | 0.85099 (19) | 0.0333 (5) | |
N1 | 0.92509 (13) | 0.13198 (9) | 0.6492 (2) | 0.0223 (5) | |
N2 | 0.66478 (14) | 0.10439 (9) | 0.3901 (2) | 0.0248 (5) | |
N3 | 0.48874 (13) | 0.11091 (9) | 0.3202 (2) | 0.0260 (5) | |
C1 | 0.95631 (18) | 0.10855 (11) | 0.8160 (3) | 0.0271 (6) | |
C2 | 1.07479 (18) | 0.12842 (12) | 0.8591 (3) | 0.0302 (7) | |
C3 | 1.0652 (2) | 0.22163 (12) | 0.6920 (3) | 0.0342 (7) | |
C4 | 0.94679 (19) | 0.20618 (11) | 0.6364 (3) | 0.0294 (6) | |
C5 | 0.80723 (16) | 0.11333 (11) | 0.6050 (3) | 0.0254 (6) | |
C6 | 0.77788 (16) | 0.12709 (12) | 0.4295 (3) | 0.0264 (6) | |
C7 | 0.63052 (17) | 0.03957 (11) | 0.3528 (3) | 0.0267 (6) | |
C8 | 0.6884 (2) | −0.02078 (12) | 0.3553 (3) | 0.0319 (7) | |
C9 | 0.6274 (2) | −0.07697 (12) | 0.3112 (3) | 0.0384 (8) | |
C10 | 0.5142 (2) | −0.07342 (13) | 0.2667 (3) | 0.0385 (8) | |
C11 | 0.4573 (2) | −0.01326 (12) | 0.2637 (3) | 0.0338 (7) | |
C12 | 0.51859 (17) | 0.04349 (11) | 0.3085 (3) | 0.0274 (6) | |
C13 | 0.57840 (16) | 0.14541 (12) | 0.3662 (3) | 0.0261 (6) | |
C14 | 0.37708 (17) | 0.13890 (12) | 0.2775 (3) | 0.0314 (7) | |
C15 | 0.3569 (2) | 0.13651 (15) | 0.0973 (3) | 0.0416 (8) | |
C16 | 0.3669 (2) | 0.20879 (14) | 0.3457 (4) | 0.0447 (8) | |
I1 | 0.68452 (1) | 0.18706 (1) | 0.00486 (2) | 0.0289 (1) | |
I2 | 0.92209 (1) | −0.07790 (1) | 0.66984 (2) | 0.0293 (1) | |
H1 | 0.971 (2) | 0.1093 (14) | 0.577 (4) | 0.044 (7)* | |
H1A | 0.906 (2) | 0.1313 (13) | 0.888 (3) | 0.037 (7)* | |
H1B | 0.945 (2) | 0.0588 (14) | 0.817 (3) | 0.036 (7)* | |
H2A | 1.091 (2) | 0.1162 (13) | 0.958 (4) | 0.034 (7)* | |
H2B | 1.123 (2) | 0.1066 (13) | 0.787 (3) | 0.034 (7)* | |
H3A | 1.072 (2) | 0.2704 (13) | 0.694 (3) | 0.033 (6)* | |
H3B | 1.117 (2) | 0.2030 (14) | 0.616 (4) | 0.046 (8)* | |
H4A | 0.892 (2) | 0.2262 (12) | 0.704 (3) | 0.031 (6)* | |
H4B | 0.936 (2) | 0.2144 (12) | 0.528 (3) | 0.030 (6)* | |
H5A | 0.7634 (19) | 0.1407 (11) | 0.676 (3) | 0.025 (6)* | |
H5B | 0.804 (2) | 0.0637 (15) | 0.630 (4) | 0.049 (8)* | |
H6A | 0.7807 (18) | 0.1741 (11) | 0.405 (3) | 0.016 (5)* | |
H6B | 0.824 (2) | 0.1001 (13) | 0.364 (3) | 0.031 (6)* | |
H8 | 0.765 (2) | −0.0215 (11) | 0.389 (3) | 0.024 (6)* | |
H9 | 0.667 (2) | −0.1179 (14) | 0.306 (3) | 0.040 (7)* | |
H10 | 0.475 (3) | −0.1117 (17) | 0.232 (4) | 0.059 (9)* | |
H11 | 0.384 (2) | −0.0104 (12) | 0.235 (3) | 0.031 (6)* | |
H13 | 0.5779 (19) | 0.1871 (12) | 0.389 (3) | 0.020 (6)* | |
H14 | 0.327 (2) | 0.1093 (13) | 0.321 (3) | 0.031 (6)* | |
H15A | 0.36430 | 0.09110 | 0.06060 | 0.0620* | |
H15B | 0.41010 | 0.16450 | 0.04710 | 0.0620* | |
H15C | 0.28350 | 0.15240 | 0.06990 | 0.0620* | |
H16A | 0.38040 | 0.20740 | 0.46000 | 0.0670* | |
H16B | 0.29360 | 0.22570 | 0.32140 | 0.0670* | |
H16C | 0.42020 | 0.23770 | 0.29890 | 0.0670* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0337 (8) | 0.0372 (8) | 0.0280 (8) | −0.0085 (7) | −0.0084 (7) | −0.0033 (7) |
N1 | 0.0170 (8) | 0.0284 (9) | 0.0214 (8) | −0.0010 (6) | −0.0008 (7) | −0.0012 (7) |
N2 | 0.0182 (8) | 0.0314 (9) | 0.0244 (9) | −0.0028 (7) | −0.0018 (7) | −0.0014 (7) |
N3 | 0.0166 (8) | 0.0364 (9) | 0.0249 (9) | −0.0031 (7) | −0.0011 (7) | 0.0018 (7) |
C1 | 0.0261 (10) | 0.0313 (11) | 0.0234 (10) | −0.0007 (9) | −0.0031 (8) | 0.0008 (9) |
C2 | 0.0267 (11) | 0.0377 (12) | 0.0255 (11) | 0.0001 (9) | −0.0065 (9) | −0.0003 (10) |
C3 | 0.0314 (12) | 0.0378 (13) | 0.0326 (12) | −0.0106 (10) | −0.0067 (10) | 0.0010 (10) |
C4 | 0.0275 (11) | 0.0269 (10) | 0.0332 (12) | −0.0030 (8) | −0.0068 (9) | 0.0027 (9) |
C5 | 0.0173 (9) | 0.0319 (11) | 0.0267 (10) | −0.0037 (8) | −0.0009 (8) | −0.0033 (9) |
C6 | 0.0156 (9) | 0.0376 (12) | 0.0257 (10) | −0.0034 (8) | −0.0022 (8) | −0.0010 (9) |
C7 | 0.0238 (10) | 0.0345 (11) | 0.0216 (10) | −0.0032 (8) | 0.0006 (8) | −0.0033 (8) |
C8 | 0.0284 (11) | 0.0393 (12) | 0.0278 (11) | 0.0006 (9) | 0.0007 (9) | −0.0037 (9) |
C9 | 0.0464 (15) | 0.0340 (12) | 0.0349 (13) | −0.0001 (10) | 0.0033 (11) | −0.0074 (10) |
C10 | 0.0454 (14) | 0.0393 (13) | 0.0307 (12) | −0.0135 (11) | 0.0013 (11) | −0.0094 (10) |
C11 | 0.0297 (12) | 0.0441 (13) | 0.0273 (11) | −0.0111 (10) | −0.0006 (9) | −0.0029 (10) |
C12 | 0.0225 (10) | 0.0354 (11) | 0.0240 (10) | −0.0044 (8) | −0.0008 (8) | −0.0010 (9) |
C13 | 0.0189 (9) | 0.0317 (11) | 0.0273 (11) | −0.0016 (8) | −0.0017 (8) | 0.0000 (9) |
C14 | 0.0139 (9) | 0.0451 (13) | 0.0348 (12) | −0.0024 (9) | −0.0026 (8) | 0.0046 (10) |
C15 | 0.0255 (11) | 0.0653 (17) | 0.0331 (13) | −0.0019 (11) | −0.0079 (10) | 0.0098 (12) |
C16 | 0.0267 (12) | 0.0520 (15) | 0.0547 (16) | 0.0092 (11) | −0.0062 (11) | −0.0001 (13) |
I1 | 0.0243 (1) | 0.0355 (1) | 0.0270 (1) | −0.0023 (1) | 0.0020 (1) | −0.0001 (1) |
I2 | 0.0219 (1) | 0.0375 (1) | 0.0288 (1) | 0.0015 (1) | 0.0046 (1) | −0.0006 (1) |
Geometric parameters (Å, º) top
O1—C2 | 1.422 (3) | C1—H1B | 1.00 (3) |
O1—C3 | 1.416 (3) | C2—H2A | 0.87 (3) |
N1—C1 | 1.499 (3) | C2—H2B | 0.96 (2) |
N1—C4 | 1.506 (3) | C3—H3A | 0.98 (3) |
N1—C5 | 1.501 (3) | C3—H3B | 0.98 (3) |
N2—C6 | 1.462 (3) | C4—H4A | 0.97 (2) |
N2—C7 | 1.387 (3) | C4—H4B | 0.92 (3) |
N2—C13 | 1.333 (3) | C5—H5A | 0.98 (2) |
N3—C12 | 1.395 (3) | C5—H5B | 1.01 (3) |
N3—C13 | 1.325 (3) | C6—H6A | 0.96 (2) |
N3—C14 | 1.488 (3) | C6—H6B | 0.96 (2) |
N1—H1 | 0.95 (3) | C8—H8 | 0.96 (2) |
C1—C2 | 1.513 (3) | C9—H9 | 0.95 (3) |
C3—C4 | 1.515 (3) | C10—H10 | 0.94 (3) |
C5—C6 | 1.515 (4) | C11—H11 | 0.91 (2) |
C7—C8 | 1.391 (3) | C13—H13 | 0.85 (2) |
C7—C12 | 1.388 (3) | C14—H14 | 0.93 (2) |
C8—C9 | 1.381 (4) | C15—H15A | 0.9600 |
C9—C10 | 1.403 (4) | C15—H15B | 0.9600 |
C10—C11 | 1.381 (4) | C15—H15C | 0.9600 |
C11—C12 | 1.393 (3) | C16—H16A | 0.9600 |
C14—C15 | 1.512 (4) | C16—H16B | 0.9600 |
C14—C16 | 1.511 (4) | C16—H16C | 0.9600 |
C1—H1A | 0.98 (3) | | |
| | | |
I1···N2 | 3.626 (3) | H1A···H4A | 2.44 (4) |
I1···C6 | 3.857 (3) | H1B···H5B | 2.26 (4) |
I1···C13 | 3.427 (3) | H1B···I2 | 3.00 (3) |
I1···C13i | 3.740 (3) | H2A···H15Cx | 2.5700 |
I2···C14ii | 3.856 (3) | H2A···I2vii | 3.21 (3) |
I2···N1iii | 3.475 (3) | H2B···H1 | 2.48 (4) |
I2···C6iii | 3.879 (3) | H2B···H3B | 2.39 (4) |
I1···H5Aiv | 3.08 (2) | H3A···I2xii | 3.23 (3) |
I1···H15B | 3.3800 | H3B···H2B | 2.39 (4) |
I1···H1Aiv | 3.09 (2) | H3B···H1 | 2.58 (4) |
I1···H13i | 2.96 (2) | H4A···H1A | 2.44 (4) |
I1···H10v | 3.09 (3) | H4A···H5A | 2.31 (3) |
I1···H6Ai | 3.13 (2) | H4B···H6A | 2.25 (3) |
I2···H3Avi | 3.23 (3) | H4B···C6 | 2.69 (2) |
I2···H8 | 3.15 (2) | H5A···H4A | 2.31 (3) |
I2···H5B | 3.17 (3) | H5A···H1A | 2.42 (3) |
I2···H1B | 3.00 (3) | H5A···I1xi | 3.08 (2) |
I2···H1iii | 2.56 (3) | H5B···H1B | 2.26 (4) |
I2···H6Biii | 3.12 (2) | H5B···I2 | 3.17 (3) |
I2···H14ii | 3.08 (2) | H5B···C7 | 3.09 (3) |
I2···H2Avii | 3.21 (3) | H6A···C4 | 2.80 (2) |
O1···C3viii | 3.275 (4) | H6A···I1viii | 3.13 (2) |
O1···N1 | 2.872 (3) | H6A···H4B | 2.25 (3) |
O1···H16Bix | 2.9100 | H6A···H13 | 2.46 (3) |
N1···O1 | 2.872 (3) | H6B···I2iii | 3.12 (2) |
N1···I2iii | 3.475 (3) | H6B···C8 | 2.91 (3) |
N2···I1 | 3.626 (3) | H6B···H1 | 2.46 (4) |
N2···N3 | 2.184 (3) | H6B···H8 | 2.54 (3) |
N3···N2 | 2.184 (3) | H8···I2 | 3.15 (2) |
C3···O1i | 3.275 (4) | H8···C6 | 2.98 (2) |
C6···I1 | 3.857 (3) | H8···H6B | 2.54 (3) |
C6···I2iii | 3.879 (3) | H10···I1v | 3.09 (3) |
C7···C11ii | 3.453 (4) | H11···H15A | 2.5000 |
C11···C15 | 3.486 (4) | H11···H14 | 2.59 (4) |
C11···C7ii | 3.453 (4) | H11···C14 | 3.00 (2) |
C13···I1viii | 3.740 (3) | H13···C16 | 2.59 (2) |
C13···I1 | 3.427 (3) | H13···H16A | 2.5200 |
C14···I2ii | 3.856 (3) | H13···H16C | 2.2500 |
C15···C11 | 3.486 (4) | H13···H6A | 2.46 (3) |
C2···H15Cx | 3.0500 | H13···I1viii | 2.96 (2) |
C4···H6A | 2.80 (2) | H14···H11 | 2.59 (4) |
C6···H4B | 2.69 (2) | H14···I2ii | 3.08 (2) |
C6···H8 | 2.98 (2) | H14···C11 | 2.96 (3) |
C7···H5B | 3.09 (3) | H15A···C11 | 2.8800 |
C8···H6B | 2.91 (3) | H15A···C12 | 2.8800 |
C11···H14 | 2.96 (3) | H15A···H11 | 2.5000 |
C11···H15A | 2.8800 | H15B···C16i | 3.0600 |
C12···H15A | 2.8800 | H15B···H16C | 2.5500 |
C13···H16C | 2.6900 | H15B···I1 | 3.3800 |
C13···H16A | 2.8300 | H15C···H16B | 2.5500 |
C14···H11 | 3.00 (2) | H15C···H2Axiii | 2.5700 |
C16···H13 | 2.59 (2) | H15C···C2xiii | 3.0500 |
C16···H15Bviii | 3.0600 | H16A···C13 | 2.8300 |
H1···H3B | 2.58 (4) | H16A···H13 | 2.5200 |
H1···H2B | 2.48 (4) | H16B···H15C | 2.5500 |
H1···H6B | 2.46 (4) | H16B···O1xiv | 2.9100 |
H1···I2iii | 2.56 (3) | H16C···H15B | 2.5500 |
H1A···H5A | 2.42 (3) | H16C···C13 | 2.6900 |
H1A···I1xi | 3.09 (2) | H16C···H13 | 2.2500 |
| | | |
C2—O1—C3 | 109.72 (17) | O1—C3—H3B | 112.0 (18) |
C1—N1—C4 | 109.51 (17) | C4—C3—H3A | 106.6 (14) |
C1—N1—C5 | 110.33 (16) | C4—C3—H3B | 110.2 (16) |
C4—N1—C5 | 113.06 (16) | H3A—C3—H3B | 109 (2) |
C6—N2—C7 | 127.20 (18) | N1—C4—H4A | 103.7 (14) |
C6—N2—C13 | 124.12 (19) | N1—C4—H4B | 103.1 (15) |
C7—N2—C13 | 108.27 (17) | C3—C4—H4A | 113.4 (15) |
C12—N3—C13 | 108.01 (17) | C3—C4—H4B | 110.8 (15) |
C12—N3—C14 | 125.33 (17) | H4A—C4—H4B | 115 (2) |
C13—N3—C14 | 126.54 (19) | N1—C5—H5A | 104.3 (14) |
C5—N1—H1 | 107.5 (16) | N1—C5—H5B | 103.7 (14) |
C1—N1—H1 | 108.0 (19) | C6—C5—H5A | 112.0 (14) |
C4—N1—H1 | 108.3 (17) | C6—C5—H5B | 111.5 (19) |
N1—C1—C2 | 109.59 (18) | H5A—C5—H5B | 113 (2) |
O1—C2—C1 | 111.34 (18) | N2—C6—H6A | 107.2 (13) |
O1—C3—C4 | 111.88 (19) | N2—C6—H6B | 105.0 (15) |
N1—C4—C3 | 110.04 (18) | C5—C6—H6A | 111.9 (15) |
N1—C5—C6 | 111.78 (17) | C5—C6—H6B | 109.3 (15) |
N2—C6—C5 | 109.71 (17) | H6A—C6—H6B | 114 (2) |
C8—C7—C12 | 122.4 (2) | C7—C8—H8 | 119.8 (13) |
N2—C7—C12 | 106.54 (18) | C9—C8—H8 | 124.4 (13) |
N2—C7—C8 | 131.1 (2) | C8—C9—H9 | 116.5 (15) |
C7—C8—C9 | 115.8 (2) | C10—C9—H9 | 121.3 (15) |
C8—C9—C10 | 122.1 (2) | C9—C10—H10 | 121 (2) |
C9—C10—C11 | 121.8 (2) | C11—C10—H10 | 117 (2) |
C10—C11—C12 | 116.2 (2) | C10—C11—H11 | 122.5 (15) |
C7—C12—C11 | 121.7 (2) | C12—C11—H11 | 121.3 (15) |
N3—C12—C7 | 106.69 (18) | N2—C13—H13 | 125.3 (16) |
N3—C12—C11 | 131.6 (2) | N3—C13—H13 | 123.8 (16) |
N2—C13—N3 | 110.5 (2) | N3—C14—H14 | 105.5 (16) |
N3—C14—C15 | 109.30 (18) | C15—C14—H14 | 106.8 (15) |
N3—C14—C16 | 110.08 (19) | C16—C14—H14 | 111.9 (16) |
C15—C14—C16 | 113.0 (2) | C14—C15—H15A | 109.00 |
N1—C1—H1A | 106.6 (15) | C14—C15—H15B | 109.00 |
N1—C1—H1B | 106.7 (14) | C14—C15—H15C | 109.00 |
C2—C1—H1A | 109.8 (15) | H15A—C15—H15B | 110.00 |
C2—C1—H1B | 112.7 (14) | H15A—C15—H15C | 109.00 |
H1A—C1—H1B | 111 (2) | H15B—C15—H15C | 109.00 |
O1—C2—H2A | 107.4 (17) | C14—C16—H16A | 109.00 |
O1—C2—H2B | 109.9 (16) | C14—C16—H16B | 109.00 |
C1—C2—H2A | 108.8 (16) | C14—C16—H16C | 109.00 |
C1—C2—H2B | 109.1 (15) | H16A—C16—H16B | 110.00 |
H2A—C2—H2B | 110 (2) | H16A—C16—H16C | 109.00 |
O1—C3—H3A | 106.6 (15) | H16B—C16—H16C | 109.00 |
| | | |
C3—O1—C2—C1 | −61.8 (2) | C13—N3—C12—C7 | 1.0 (3) |
C2—O1—C3—C4 | 60.7 (2) | C14—N3—C12—C11 | −2.8 (4) |
C4—N1—C1—C2 | −54.3 (2) | C12—N3—C13—N2 | −1.9 (3) |
C1—N1—C4—C3 | 53.2 (2) | C14—N3—C13—N2 | −178.10 (19) |
C5—N1—C1—C2 | −179.39 (17) | C14—N3—C12—C7 | 177.3 (2) |
C5—N1—C4—C3 | 176.69 (19) | C13—N3—C12—C11 | −179.1 (3) |
C1—N1—C5—C6 | −171.71 (18) | N1—C1—C2—O1 | 59.3 (2) |
C4—N1—C5—C6 | 65.3 (2) | O1—C3—C4—N1 | −57.0 (2) |
C7—N2—C13—N3 | 1.9 (3) | N1—C5—C6—N2 | 176.58 (17) |
C7—N2—C6—C5 | −82.3 (3) | N2—C7—C12—N3 | 0.1 (3) |
C6—N2—C7—C8 | 6.2 (4) | C8—C7—C12—N3 | 179.9 (2) |
C6—N2—C7—C12 | −174.1 (2) | C8—C7—C12—C11 | 0.0 (4) |
C13—N2—C7—C12 | −1.2 (3) | C12—C7—C8—C9 | −0.2 (4) |
C13—N2—C7—C8 | 179.0 (3) | N2—C7—C8—C9 | 179.6 (2) |
C6—N2—C13—N3 | 175.07 (19) | N2—C7—C12—C11 | −179.8 (2) |
C13—N2—C6—C5 | 106.0 (2) | C7—C8—C9—C10 | 0.0 (4) |
C12—N3—C14—C15 | −70.3 (3) | C8—C9—C10—C11 | 0.3 (4) |
C13—N3—C14—C16 | −19.3 (3) | C9—C10—C11—C12 | −0.5 (4) |
C13—N3—C14—C15 | 105.4 (3) | C10—C11—C12—C7 | 0.3 (4) |
C12—N3—C14—C16 | 165.1 (2) | C10—C11—C12—N3 | −179.6 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+1; (iv) x, y, z−1; (v) −x+1, −y, −z; (vi) −x+2, y−1/2, −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) x−1, y, z−1; (xiv) x−1, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I2iii | 0.95 (3) | 2.56 (3) | 3.475 (3) | 163 (2) |
C1—H1B···I2 | 1.00 (3) | 3.00 (3) | 3.926 (3) | 155.2 (19) |
C13—H13···I1viii | 0.85 (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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