The title salt, C
11H
15N
2+·I
−, crystallizes with two formula units in the asymmetric unit. The two crystallographically unique cations form alternating columns along the
a axis, linked by protruding ethyl groups and interspersed with iodide counter-ions. Cations in a given column stack in centrosymmetrically related pairs with interionic C
C and C
N distances consistent with substantial π–π bonding. One of the iodide ions appears to form a weak hydrogen bond with the most acidic proton in one of the cations.
Supporting information
CCDC reference: 232136
Key indicators
- Single-crystal X-ray study
- T = 277 K
- Mean (C-C) = 0.008 Å
- R factor = 0.041
- wR factor = 0.114
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.98
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.91 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.42 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1A
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2A
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
1,3-diethylbenzimidazolium iodide
top
Crystal data top
C11H15N2+·I− | F(000) = 1184 |
Mr = 302.15 | Dx = 1.607 Mg m−3 |
Monoclinic, P21/c | Melting point: 510 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2578 (5) Å | Cell parameters from 900 reflections |
b = 14.6014 (7) Å | θ = 2.7–22.5° |
c = 15.1903 (5) Å | µ = 2.53 mm−1 |
β = 90.212 (3)° | T = 277 K |
V = 2496.96 (18) Å3 | Rod, colorless |
Z = 8 | 0.50 × 0.10 × 0.04 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4368 independent reflections |
Radiation source: fine-focus sealed tube | 3384 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −12→13 |
Tmin = 0.690, Tmax = 0.904 | k = −16→17 |
17742 measured reflections | l = −18→18 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0654P)2 + 2.1072P] where P = (Fo2 + 2Fc2)/3 |
4368 reflections | (Δ/σ)max = 0.001 |
257 parameters | Δρmax = 1.18 e Å−3 |
2 restraints | Δρmin = −0.40 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 | |
I1 | 0.22285 (4) | 0.77617 (3) | 0.22484 (2) | 0.07140 (16) | |
N21 | 0.5984 (4) | 0.4339 (3) | 0.8401 (2) | 0.0575 (10) | |
N23 | 0.5236 (4) | 0.3344 (3) | 0.9316 (3) | 0.0572 (10) | |
C2A | 0.6360 (6) | 0.4777 (5) | 0.7569 (4) | 0.0856 (18) | |
C2B | 0.5408 (8) | 0.4852 (8) | 0.6926 (5) | 0.164 (5) | |
C21 | 0.6374 (4) | 0.4591 (3) | 0.9234 (3) | 0.0532 (11) | |
C22 | 0.5334 (5) | 0.3590 (4) | 0.8478 (3) | 0.0601 (12) | |
C23 | 0.5897 (4) | 0.3951 (3) | 0.9814 (3) | 0.0533 (11) | |
C24 | 0.6102 (5) | 0.4016 (4) | 1.0713 (3) | 0.0664 (14) | |
C25 | 0.6799 (5) | 0.4736 (5) | 1.0992 (4) | 0.0792 (17) | |
C26 | 0.7256 (5) | 0.5376 (5) | 1.0417 (4) | 0.0737 (16) | |
C27 | 0.7066 (5) | 0.5324 (4) | 0.9526 (4) | 0.0645 (13) | |
C28 | 0.4537 (6) | 0.2560 (4) | 0.9634 (4) | 0.0726 (15) | |
C29 | 0.5307 (6) | 0.1757 (5) | 0.9863 (5) | 0.099 (2) | |
H2A1 | 0.6662 | 0.5384 | 0.7698 | 0.103* | |
H2A2 | 0.7003 | 0.4423 | 0.7316 | 0.103* | |
H2B1 | 0.5120 | 0.4252 | 0.6781 | 0.246* | |
H2B2 | 0.5702 | 0.5144 | 0.6404 | 0.246* | |
H2B3 | 0.4773 | 0.5210 | 0.7168 | 0.246* | |
H22 | 0.4990 | 0.3277 | 0.8008 | 0.072* | |
H24 | 0.5786 | 0.3595 | 1.1107 | 0.080* | |
H25 | 0.6967 | 0.4793 | 1.1589 | 0.095* | |
H26 | 0.7707 | 0.5857 | 1.0640 | 0.088* | |
H27 | 0.7381 | 0.5753 | 0.9138 | 0.077* | |
H28A | 0.3972 | 0.2379 | 0.9182 | 0.087* | |
H28B | 0.4092 | 0.2743 | 1.0150 | 0.087* | |
H29A | 0.5790 | 0.1599 | 0.9365 | 0.149* | |
H29B | 0.4816 | 0.1244 | 1.0016 | 0.149* | |
H29C | 0.5809 | 0.1912 | 1.0353 | 0.149* | |
I2 | 0.28172 (4) | 0.24859 (3) | 0.21393 (3) | 0.07422 (16) | |
N11 | 0.0127 (3) | 0.5644 (3) | 0.3303 (2) | 0.0544 (10) | |
N13 | 0.0819 (4) | 0.6593 (3) | 0.4283 (2) | 0.0539 (10) | |
C1A | 0.1147 (6) | 0.7462 (4) | 0.4718 (4) | 0.0809 (18) | |
C1B | 0.0183 (9) | 0.8142 (6) | 0.4711 (8) | 0.152 (4) | |
C11 | 0.0826 (4) | 0.5133 (3) | 0.3881 (3) | 0.0539 (12) | |
C12 | 0.0168 (4) | 0.6509 (4) | 0.3562 (3) | 0.0569 (12) | |
C13 | 0.1249 (4) | 0.5730 (3) | 0.4507 (3) | 0.0523 (11) | |
C14 | 0.1947 (4) | 0.5441 (4) | 0.5211 (3) | 0.0653 (14) | |
C15 | 0.2197 (5) | 0.4507 (5) | 0.5241 (5) | 0.0816 (18) | |
C16 | 0.1782 (6) | 0.3919 (5) | 0.4597 (5) | 0.086 (2) | |
C17 | 0.1086 (5) | 0.4207 (4) | 0.3915 (4) | 0.0729 (15) | |
C18 | −0.0536 (5) | 0.5316 (4) | 0.2527 (3) | 0.0682 (14) | |
C19 | 0.0257 (7) | 0.5164 (6) | 0.1759 (4) | 0.108 (3) | |
H1A1 | 0.1370 | 0.7336 | 0.5324 | 0.097* | |
H1A2 | 0.1834 | 0.7720 | 0.4425 | 0.097* | |
H1B1 | 0.0007 | 0.8313 | 0.4114 | 0.228* | |
H1B2 | 0.0426 | 0.8674 | 0.5037 | 0.228* | |
H1B3 | −0.0513 | 0.7883 | 0.4976 | 0.228* | |
H12 | −0.0209 | 0.6992 | 0.3275 | 0.068* | |
H14 | 0.2229 | 0.5846 | 0.5635 | 0.078* | |
H15 | 0.2651 | 0.4276 | 0.5702 | 0.098* | |
H16 | 0.1986 | 0.3302 | 0.4631 | 0.104* | |
H17 | 0.0799 | 0.3801 | 0.3493 | 0.087* | |
H18A | −0.1139 | 0.5763 | 0.2371 | 0.082* | |
H18B | −0.0934 | 0.4747 | 0.2672 | 0.082* | |
H19A | 0.0612 | 0.5735 | 0.1589 | 0.163* | |
H19B | −0.0198 | 0.4924 | 0.1276 | 0.163* | |
H19C | 0.0869 | 0.4736 | 0.1918 | 0.163* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0868 (3) | 0.0720 (3) | 0.0555 (2) | 0.00469 (19) | 0.00713 (18) | 0.00111 (16) |
N21 | 0.065 (3) | 0.058 (3) | 0.049 (2) | −0.001 (2) | 0.0037 (19) | 0.0050 (18) |
N23 | 0.057 (2) | 0.054 (2) | 0.060 (2) | −0.0018 (19) | 0.0070 (19) | 0.0034 (19) |
C2A | 0.111 (5) | 0.080 (4) | 0.065 (4) | −0.008 (4) | 0.016 (3) | 0.013 (3) |
C2B | 0.165 (8) | 0.258 (14) | 0.070 (5) | −0.063 (9) | −0.023 (5) | 0.073 (6) |
C21 | 0.049 (3) | 0.055 (3) | 0.056 (3) | 0.010 (2) | 0.003 (2) | 0.000 (2) |
C22 | 0.065 (3) | 0.064 (3) | 0.051 (3) | 0.000 (3) | 0.006 (2) | −0.008 (2) |
C23 | 0.047 (3) | 0.060 (3) | 0.052 (3) | 0.009 (2) | 0.005 (2) | 0.002 (2) |
C24 | 0.064 (3) | 0.083 (4) | 0.053 (3) | 0.014 (3) | 0.002 (2) | 0.006 (3) |
C25 | 0.071 (4) | 0.101 (5) | 0.066 (3) | 0.018 (3) | −0.017 (3) | −0.011 (3) |
C26 | 0.063 (4) | 0.075 (4) | 0.084 (4) | 0.003 (3) | −0.013 (3) | −0.013 (3) |
C27 | 0.055 (3) | 0.061 (3) | 0.077 (3) | 0.003 (2) | 0.002 (3) | 0.001 (3) |
C28 | 0.068 (4) | 0.070 (4) | 0.079 (4) | −0.007 (3) | 0.012 (3) | 0.009 (3) |
C29 | 0.091 (5) | 0.070 (4) | 0.137 (6) | −0.005 (3) | 0.024 (4) | 0.026 (4) |
I2 | 0.0756 (3) | 0.0661 (3) | 0.0809 (3) | −0.00430 (18) | −0.0178 (2) | −0.00358 (17) |
N11 | 0.058 (2) | 0.054 (3) | 0.052 (2) | −0.0058 (18) | −0.0009 (18) | −0.0009 (18) |
N13 | 0.065 (3) | 0.053 (2) | 0.044 (2) | −0.0064 (19) | 0.0003 (18) | 0.0007 (17) |
C1A | 0.105 (5) | 0.076 (4) | 0.062 (3) | −0.012 (3) | −0.017 (3) | −0.008 (3) |
C1B | 0.171 (9) | 0.064 (5) | 0.221 (11) | 0.035 (5) | −0.060 (8) | −0.054 (6) |
C11 | 0.047 (3) | 0.055 (3) | 0.060 (3) | 0.000 (2) | 0.013 (2) | 0.007 (2) |
C12 | 0.062 (3) | 0.055 (3) | 0.053 (3) | 0.000 (2) | 0.000 (2) | 0.001 (2) |
C13 | 0.046 (3) | 0.063 (3) | 0.048 (2) | 0.000 (2) | 0.010 (2) | 0.005 (2) |
C14 | 0.053 (3) | 0.089 (4) | 0.054 (3) | −0.001 (3) | 0.005 (2) | 0.010 (3) |
C15 | 0.063 (4) | 0.092 (5) | 0.090 (4) | 0.017 (3) | 0.006 (3) | 0.031 (4) |
C16 | 0.075 (4) | 0.065 (4) | 0.120 (5) | 0.022 (3) | 0.023 (4) | 0.026 (4) |
C17 | 0.069 (4) | 0.058 (3) | 0.092 (4) | 0.003 (3) | 0.020 (3) | −0.004 (3) |
C18 | 0.066 (3) | 0.065 (3) | 0.073 (4) | −0.009 (3) | −0.010 (3) | −0.012 (3) |
C19 | 0.102 (5) | 0.156 (8) | 0.068 (4) | −0.017 (5) | −0.007 (4) | −0.034 (4) |
Geometric parameters (Å, º) top
N11—C12 | 1.323 (6) | C2A—H2A1 | 0.9700 |
N13—C12 | 1.321 (6) | C2A—H2A2 | 0.9700 |
N11—C11 | 1.394 (6) | C14—H14 | 0.9300 |
N13—C13 | 1.392 (6) | C26—H26 | 0.9300 |
C11—C13 | 1.375 (7) | C17—H17 | 0.9300 |
C11—C17 | 1.385 (7) | C16—H16 | 0.9300 |
C13—C14 | 1.389 (7) | C28—C29 | 1.499 (9) |
C14—C15 | 1.393 (10) | C28—H28A | 0.9700 |
C15—C16 | 1.381 (10) | C28—H28B | 0.9700 |
C16—C17 | 1.364 (9) | C25—H25 | 0.9300 |
N21—C22 | 1.322 (6) | C15—H15 | 0.9300 |
N23—C22 | 1.328 (6) | C29—H29A | 0.9600 |
N21—C21 | 1.387 (6) | C29—H29B | 0.9600 |
N23—C23 | 1.382 (6) | C29—H29C | 0.9600 |
C21—C23 | 1.393 (7) | C1A—C1B | 1.470 (7) |
C21—C27 | 1.395 (7) | C1A—H1A1 | 0.9700 |
C23—C24 | 1.387 (7) | C1A—H1A2 | 0.9700 |
C24—C25 | 1.378 (9) | C18—C19 | 1.488 (8) |
C25—C26 | 1.380 (9) | C18—H18A | 0.9700 |
C26—C27 | 1.372 (8) | C18—H18B | 0.9700 |
N13—C1A | 1.477 (7) | C1B—H1B1 | 0.9600 |
N23—C28 | 1.472 (7) | C1B—H1B2 | 0.9600 |
N11—C18 | 1.473 (6) | C1B—H1B3 | 0.9600 |
N21—C2A | 1.479 (6) | C19—H19A | 0.9600 |
C22—H22 | 0.9300 | C19—H19B | 0.9600 |
C12—H12 | 0.9300 | C19—H19C | 0.9600 |
C24—H24 | 0.9300 | C2B—H2B1 | 0.9600 |
C27—H27 | 0.9300 | C2B—H2B2 | 0.9600 |
C2A—C2B | 1.451 (7) | C2B—H2B3 | 0.9600 |
| | | |
C12—N13—C13 | 108.1 (4) | C17—C16—C15 | 122.5 (6) |
C12—N13—C1A | 126.0 (4) | C17—C16—H16 | 118.7 |
C13—N13—C1A | 125.5 (4) | C15—C16—H16 | 118.7 |
C22—N23—C23 | 107.7 (4) | N23—C28—C29 | 112.0 (5) |
C22—N23—C28 | 124.8 (5) | N23—C28—H28A | 109.2 |
C23—N23—C28 | 127.4 (4) | C29—C28—H28A | 109.2 |
C12—N11—C11 | 107.7 (4) | N23—C28—H28B | 109.2 |
C12—N11—C18 | 124.4 (4) | C29—C28—H28B | 109.2 |
C11—N11—C18 | 127.8 (4) | H28A—C28—H28B | 107.9 |
C11—C13—C14 | 122.2 (5) | C24—C25—C26 | 122.3 (5) |
C11—C13—N13 | 106.6 (4) | C24—C25—H25 | 118.8 |
C14—C13—N13 | 131.2 (5) | C26—C25—H25 | 118.8 |
C22—N21—C21 | 108.2 (4) | C16—C15—C14 | 121.2 (6) |
C22—N21—C2A | 126.4 (4) | C16—C15—H15 | 119.4 |
C21—N21—C2A | 125.0 (4) | C14—C15—H15 | 119.4 |
N21—C22—N23 | 110.9 (4) | C28—C29—H29A | 109.5 |
N21—C22—H22 | 124.6 | C28—C29—H29B | 109.5 |
N23—C22—H22 | 124.6 | H29A—C29—H29B | 109.5 |
N23—C23—C24 | 132.1 (5) | C28—C29—H29C | 109.5 |
N23—C23—C21 | 107.0 (4) | H29A—C29—H29C | 109.5 |
C24—C23—C21 | 120.9 (5) | H29B—C29—H29C | 109.5 |
N21—C21—C23 | 106.1 (4) | C1B—C1A—N13 | 113.1 (6) |
N21—C21—C27 | 131.9 (5) | C1B—C1A—H1A1 | 109.0 |
C23—C21—C27 | 122.0 (5) | N13—C1A—H1A1 | 109.0 |
C13—C11—C17 | 121.5 (5) | C1B—C1A—H1A2 | 109.0 |
C13—C11—N11 | 106.8 (4) | N13—C1A—H1A2 | 109.0 |
C17—C11—N11 | 131.7 (5) | H1A1—C1A—H1A2 | 107.8 |
N13—C12—N11 | 110.7 (4) | N11—C18—C19 | 111.8 (5) |
N13—C12—H12 | 124.6 | N11—C18—H18A | 109.3 |
N11—C12—H12 | 124.6 | C19—C18—H18A | 109.3 |
C25—C24—C23 | 116.6 (5) | N11—C18—H18B | 109.3 |
C25—C24—H24 | 121.7 | C19—C18—H18B | 109.3 |
C23—C24—H24 | 121.7 | H18A—C18—H18B | 107.9 |
C26—C27—C21 | 116.1 (5) | C1A—C1B—H1B1 | 109.5 |
C26—C27—H27 | 121.9 | C1A—C1B—H1B2 | 109.5 |
C21—C27—H27 | 121.9 | H1B1—C1B—H1B2 | 109.5 |
C2B—C2A—N21 | 113.3 (5) | C1A—C1B—H1B3 | 109.5 |
C2B—C2A—H2A1 | 108.9 | H1B1—C1B—H1B3 | 109.5 |
N21—C2A—H2A1 | 108.9 | H1B2—C1B—H1B3 | 109.5 |
C2B—C2A—H2A2 | 108.9 | C18—C19—H19A | 109.5 |
N21—C2A—H2A2 | 108.9 | C18—C19—H19B | 109.5 |
H2A1—C2A—H2A2 | 107.7 | H19A—C19—H19B | 109.5 |
C13—C14—C15 | 115.9 (6) | C18—C19—H19C | 109.5 |
C13—C14—H14 | 122.1 | H19A—C19—H19C | 109.5 |
C15—C14—H14 | 122.1 | H19B—C19—H19C | 109.5 |
C27—C26—C25 | 122.0 (6) | C2A—C2B—H2B1 | 109.5 |
C27—C26—H26 | 119.0 | C2A—C2B—H2B2 | 109.5 |
C25—C26—H26 | 119.0 | H2B1—C2B—H2B2 | 109.5 |
C16—C17—C11 | 116.7 (6) | C2A—C2B—H2B3 | 109.5 |
C16—C17—H17 | 121.6 | H2B1—C2B—H2B3 | 109.5 |
C11—C17—H17 | 121.6 | H2B2—C2B—H2B3 | 109.5 |
| | | |
C12—N13—C13—C11 | 0.3 (5) | C18—N11—C11—C17 | −1.2 (8) |
C1A—N13—C13—C11 | −173.4 (5) | C13—N13—C12—N11 | 0.9 (5) |
C12—N13—C13—C14 | −178.4 (5) | C1A—N13—C12—N11 | 174.6 (5) |
C1A—N13—C13—C14 | 7.9 (8) | C11—N11—C12—N13 | −1.7 (5) |
C21—N21—C22—N23 | 1.9 (6) | C18—N11—C12—N13 | 179.2 (4) |
C2A—N21—C22—N23 | 175.2 (5) | N23—C23—C24—C25 | −178.4 (5) |
C23—N23—C22—N21 | −2.2 (6) | C21—C23—C24—C25 | −0.4 (7) |
C28—N23—C22—N21 | 177.7 (5) | N21—C21—C27—C26 | 178.3 (5) |
C22—N23—C23—C24 | 179.8 (5) | C23—C21—C27—C26 | 0.3 (7) |
C28—N23—C23—C24 | 0.0 (9) | C22—N21—C2A—C2B | 45.3 (10) |
C22—N23—C23—C21 | 1.5 (5) | C21—N21—C2A—C2B | −142.5 (8) |
C28—N23—C23—C21 | −178.3 (5) | C11—C13—C14—C15 | 0.3 (7) |
C22—N21—C21—C23 | −0.9 (5) | N13—C13—C14—C15 | 178.8 (5) |
C2A—N21—C21—C23 | −174.2 (5) | C21—C27—C26—C25 | 0.6 (8) |
C22—N21—C21—C27 | −179.2 (5) | C13—C11—C17—C16 | −0.1 (7) |
C2A—N21—C21—C27 | 7.5 (8) | N11—C11—C17—C16 | −177.9 (5) |
N23—C23—C21—N21 | −0.4 (5) | C11—C17—C16—C15 | 1.4 (9) |
C24—C23—C21—N21 | −178.9 (4) | C22—N23—C28—C29 | 102.9 (7) |
N23—C23—C21—C27 | 178.1 (4) | C23—N23—C28—C29 | −77.3 (7) |
C24—C23—C21—C27 | −0.4 (7) | C23—C24—C25—C26 | 1.3 (8) |
C14—C13—C11—C17 | −0.7 (7) | C27—C26—C25—C24 | −1.4 (9) |
N13—C13—C11—C17 | −179.5 (4) | C17—C16—C15—C14 | −1.8 (9) |
C14—C13—C11—N11 | 177.5 (4) | C13—C14—C15—C16 | 0.9 (8) |
N13—C13—C11—N11 | −1.3 (5) | C12—N13—C1A—C1B | 38.5 (9) |
C12—N11—C11—C13 | 1.9 (5) | C13—N13—C1A—C1B | −148.9 (7) |
C18—N11—C11—C13 | −179.1 (4) | C12—N11—C18—C19 | 100.9 (7) |
C12—N11—C11—C17 | 179.8 (5) | C11—N11—C18—C19 | −78.0 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···I2i | 0.93 | 2.99 | 3.820 (5) | 149 |
Symmetry code: (i) x, −y+1/2, z+1/2. |