The title compound, C
26H
24N
4, contains one pyrazole ring and two phenyl rings, which are nearly perpendicular to the benzimidazole ring system. In the structure, there is one intramolecular C—H
N hydrogen-bonding interaction.
Supporting information
CCDC reference: 282258
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.130
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - N4 .. 13.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N4 - C11 .. 13.64 su
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.120
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ?
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-Benzyl-2-[1-(5-methyl-1
H-pyrazol-3-yl)-2-phenylethyl]benzimidazole
top
Crystal data top
C26H24N4 | Z = 2 |
Mr = 392.49 | F(000) = 416 |
Triclinic, P1 | Dx = 1.219 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.244 (5) Å | Cell parameters from 21742 reflections |
b = 10.601 (5) Å | θ = 2.2–27.9° |
c = 11.404 (5) Å | µ = 0.07 mm−1 |
α = 64.499 (5)° | T = 296 K |
β = 74.587 (5)° | Prism, colourless |
γ = 89.556 (5)° | 0.62 × 0.53 × 0.47 mm |
V = 1069.5 (9) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 3537 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.120 |
Plane graphite monochromator | θmax = 27.8°, θmin = 2.5° |
Detector resolution: 6.67 pixels mm-1 | h = −13→13 |
ω scans | k = −13→13 |
17823 measured reflections | l = −14→14 |
4925 independent 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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0685P)2 + 0.0775P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4925 reflections | Δρmax = 0.24 e Å−3 |
273 parameters | Δρmin = −0.32 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: 0.020 (5) |
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 | |
N1 | 0.15104 (11) | 0.25192 (14) | 0.84680 (13) | 0.0551 (4) | |
N2 | 0.37136 (10) | 0.30826 (11) | 0.72481 (11) | 0.0433 (3) | |
N3 | 0.30782 (14) | 0.68272 (14) | 0.62471 (14) | 0.0638 (4) | |
N4 | 0.23158 (14) | 0.77030 (12) | 0.54349 (12) | 0.0589 (4) | |
C1 | 0.32488 (13) | 0.19085 (14) | 0.71697 (13) | 0.0463 (4) | |
C2 | 0.38997 (17) | 0.11345 (17) | 0.65128 (17) | 0.0626 (5) | |
C3 | 0.3108 (2) | 0.00066 (19) | 0.6651 (2) | 0.0734 (7) | |
C4 | 0.1740 (2) | −0.03397 (19) | 0.7405 (2) | 0.0735 (6) | |
C5 | 0.11044 (17) | 0.04269 (18) | 0.80536 (18) | 0.0651 (6) | |
C6 | 0.18809 (13) | 0.15788 (15) | 0.79274 (15) | 0.0498 (4) | |
C7 | 0.26220 (12) | 0.33793 (14) | 0.80472 (13) | 0.0444 (4) | |
C8 | 0.26849 (13) | 0.46503 (15) | 0.83118 (15) | 0.0507 (4) | |
C9 | 0.21949 (14) | 0.58189 (14) | 0.72643 (14) | 0.0506 (4) | |
C10 | 0.08652 (16) | 0.59911 (17) | 0.71590 (16) | 0.0603 (5) | |
C11 | 0.10042 (18) | 0.71727 (17) | 0.60033 (17) | 0.0643 (6) | |
C12 | 0.0007 (3) | 0.7942 (3) | 0.5298 (2) | 0.0941 (8) | |
C13 | 0.18329 (15) | 0.43342 (17) | 0.97635 (15) | 0.0578 (5) | |
C14 | 0.24215 (14) | 0.33442 (16) | 1.08429 (15) | 0.0535 (4) | |
C15 | 0.3237 (2) | 0.3852 (2) | 1.1379 (2) | 0.0758 (7) | |
C16 | 0.3790 (2) | 0.2947 (3) | 1.2352 (3) | 0.0957 (9) | |
C17 | 0.3560 (2) | 0.1516 (3) | 1.2810 (2) | 0.0903 (8) | |
C18 | 0.2770 (2) | 0.0997 (2) | 1.2287 (2) | 0.0818 (7) | |
C19 | 0.21962 (18) | 0.19002 (18) | 1.13281 (17) | 0.0679 (5) | |
C20 | 0.51037 (13) | 0.37901 (14) | 0.66243 (13) | 0.0476 (4) | |
C21 | 0.60646 (13) | 0.32036 (14) | 0.74780 (14) | 0.0482 (4) | |
C22 | 0.74445 (15) | 0.3639 (2) | 0.68612 (19) | 0.0658 (5) | |
C23 | 0.83745 (17) | 0.3166 (3) | 0.7591 (3) | 0.0827 (8) | |
C24 | 0.7943 (2) | 0.2264 (3) | 0.8930 (3) | 0.0899 (9) | |
C25 | 0.6587 (2) | 0.1817 (3) | 0.9557 (2) | 0.0895 (8) | |
C26 | 0.56388 (17) | 0.22785 (19) | 0.88297 (18) | 0.0687 (5) | |
H2 | 0.48150 | 0.13650 | 0.60100 | 0.0750* | |
H3 | 0.35000 | −0.05390 | 0.62260 | 0.0880* | |
H4 | 0.12430 | −0.11110 | 0.74730 | 0.0880* | |
H4A | 0.26410 | 0.84580 | 0.46920 | 0.0710* | |
H5 | 0.01900 | 0.01870 | 0.85580 | 0.0780* | |
H8 | 0.36370 | 0.49310 | 0.81960 | 0.0610* | |
H10 | 0.00630 | 0.54140 | 0.77570 | 0.0720* | |
H12A | 0.00810 | 0.88970 | 0.51720 | 0.1410* | |
H12B | −0.09010 | 0.74890 | 0.58360 | 0.1410* | |
H12C | 0.01960 | 0.79360 | 0.44290 | 0.1410* | |
H13A | 0.17600 | 0.52130 | 0.98360 | 0.0690* | |
H13B | 0.09190 | 0.39300 | 0.99240 | 0.0690* | |
H15 | 0.34100 | 0.48180 | 1.10760 | 0.0910* | |
H16 | 0.43270 | 0.33060 | 1.27060 | 0.1150* | |
H17 | 0.39390 | 0.09080 | 1.34690 | 0.1080* | |
H18 | 0.26190 | 0.00310 | 1.25790 | 0.0980* | |
H19 | 0.16410 | 0.15300 | 1.09970 | 0.0810* | |
H20A | 0.50800 | 0.47780 | 0.64150 | 0.0570* | |
H20B | 0.54690 | 0.37360 | 0.57730 | 0.0570* | |
H22 | 0.77510 | 0.42590 | 0.59420 | 0.0790* | |
H23 | 0.93000 | 0.34690 | 0.71620 | 0.0990* | |
H24 | 0.85700 | 0.19500 | 0.94210 | 0.1080* | |
H25 | 0.62920 | 0.11980 | 1.04780 | 0.1070* | |
H26 | 0.47160 | 0.19580 | 0.92630 | 0.0820* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0381 (6) | 0.0676 (7) | 0.0729 (8) | 0.0064 (5) | −0.0153 (5) | −0.0438 (6) |
N2 | 0.0369 (5) | 0.0483 (5) | 0.0487 (6) | 0.0083 (4) | −0.0125 (4) | −0.0253 (5) |
N3 | 0.0602 (8) | 0.0604 (7) | 0.0644 (8) | −0.0037 (6) | −0.0059 (6) | −0.0289 (6) |
N4 | 0.0696 (8) | 0.0442 (6) | 0.0484 (6) | 0.0000 (5) | −0.0060 (6) | −0.0138 (5) |
C1 | 0.0480 (7) | 0.0478 (7) | 0.0501 (7) | 0.0108 (5) | −0.0202 (5) | −0.0248 (6) |
C2 | 0.0628 (9) | 0.0620 (9) | 0.0688 (9) | 0.0114 (7) | −0.0120 (7) | −0.0385 (8) |
C3 | 0.0870 (13) | 0.0677 (10) | 0.0846 (12) | 0.0141 (9) | −0.0241 (10) | −0.0515 (9) |
C4 | 0.0866 (12) | 0.0649 (9) | 0.0873 (12) | 0.0017 (8) | −0.0359 (10) | −0.0440 (9) |
C5 | 0.0566 (9) | 0.0678 (9) | 0.0824 (11) | −0.0013 (7) | −0.0243 (8) | −0.0412 (9) |
C6 | 0.0445 (7) | 0.0563 (7) | 0.0592 (8) | 0.0077 (5) | −0.0217 (6) | −0.0313 (6) |
C7 | 0.0349 (6) | 0.0533 (7) | 0.0523 (7) | 0.0091 (5) | −0.0142 (5) | −0.0292 (6) |
C8 | 0.0403 (6) | 0.0584 (8) | 0.0620 (8) | 0.0049 (5) | −0.0114 (6) | −0.0366 (7) |
C9 | 0.0502 (7) | 0.0510 (7) | 0.0557 (7) | 0.0032 (6) | −0.0067 (6) | −0.0332 (6) |
C10 | 0.0530 (8) | 0.0602 (8) | 0.0608 (9) | 0.0079 (6) | −0.0089 (7) | −0.0251 (7) |
C11 | 0.0765 (11) | 0.0605 (9) | 0.0604 (9) | 0.0184 (8) | −0.0154 (8) | −0.0337 (7) |
C12 | 0.1039 (16) | 0.0928 (14) | 0.0806 (13) | 0.0416 (12) | −0.0318 (12) | −0.0317 (11) |
C13 | 0.0544 (8) | 0.0666 (9) | 0.0609 (8) | 0.0151 (7) | −0.0133 (7) | −0.0381 (7) |
C14 | 0.0468 (7) | 0.0609 (8) | 0.0565 (8) | 0.0053 (6) | −0.0082 (6) | −0.0333 (7) |
C15 | 0.0855 (12) | 0.0666 (10) | 0.0842 (12) | −0.0009 (9) | −0.0341 (10) | −0.0360 (9) |
C16 | 0.0855 (14) | 0.1117 (17) | 0.1003 (15) | 0.0003 (12) | −0.0490 (12) | −0.0435 (14) |
C17 | 0.0800 (13) | 0.0960 (15) | 0.0821 (13) | 0.0251 (11) | −0.0292 (11) | −0.0251 (11) |
C18 | 0.0971 (14) | 0.0581 (9) | 0.0706 (11) | 0.0091 (9) | −0.0102 (10) | −0.0192 (9) |
C19 | 0.0715 (10) | 0.0636 (9) | 0.0649 (9) | −0.0064 (8) | −0.0100 (8) | −0.0306 (8) |
C20 | 0.0402 (6) | 0.0502 (7) | 0.0471 (7) | 0.0049 (5) | −0.0065 (5) | −0.0204 (6) |
C21 | 0.0394 (6) | 0.0531 (7) | 0.0596 (8) | 0.0094 (5) | −0.0140 (6) | −0.0322 (6) |
C22 | 0.0443 (8) | 0.0803 (10) | 0.0783 (10) | 0.0023 (7) | −0.0113 (7) | −0.0438 (9) |
C23 | 0.0414 (8) | 0.1148 (16) | 0.1172 (17) | 0.0142 (9) | −0.0277 (9) | −0.0717 (15) |
C24 | 0.0684 (12) | 0.1205 (17) | 0.1149 (18) | 0.0389 (12) | −0.0545 (12) | −0.0674 (16) |
C25 | 0.0838 (14) | 0.1036 (15) | 0.0776 (12) | 0.0297 (11) | −0.0411 (11) | −0.0273 (11) |
C26 | 0.0504 (8) | 0.0793 (11) | 0.0628 (9) | 0.0134 (7) | −0.0176 (7) | −0.0188 (8) |
Geometric parameters (Å, º) top
N1—C6 | 1.385 (2) | C21—C26 | 1.370 (2) |
N1—C7 | 1.307 (2) | C21—C22 | 1.381 (2) |
N2—C1 | 1.383 (2) | C22—C23 | 1.381 (3) |
N2—C7 | 1.3710 (19) | C23—C24 | 1.354 (4) |
N2—C20 | 1.4543 (19) | C24—C25 | 1.362 (3) |
N3—N4 | 1.401 (2) | C25—C26 | 1.394 (3) |
N3—C9 | 1.302 (2) | C2—H2 | 0.9300 |
N4—C11 | 1.333 (2) | C3—H3 | 0.9300 |
N4—H4A | 0.8600 | C4—H4 | 0.9300 |
C1—C2 | 1.391 (3) | C5—H5 | 0.9300 |
C1—C6 | 1.392 (2) | C8—H8 | 0.9800 |
C2—C3 | 1.377 (3) | C10—H10 | 0.9300 |
C3—C4 | 1.391 (3) | C12—H12A | 0.9600 |
C4—C5 | 1.373 (3) | C12—H12B | 0.9600 |
C5—C6 | 1.396 (3) | C12—H12C | 0.9600 |
C7—C8 | 1.508 (2) | C13—H13A | 0.9700 |
C8—C9 | 1.500 (2) | C13—H13B | 0.9700 |
C8—C13 | 1.541 (2) | C15—H15 | 0.9300 |
C9—C10 | 1.403 (2) | C16—H16 | 0.9300 |
C10—C11 | 1.345 (3) | C17—H17 | 0.9300 |
C11—C12 | 1.488 (4) | C18—H18 | 0.9300 |
C13—C14 | 1.501 (2) | C19—H19 | 0.9300 |
C14—C19 | 1.382 (3) | C20—H20A | 0.9700 |
C14—C15 | 1.387 (3) | C20—H20B | 0.9700 |
C15—C16 | 1.372 (4) | C22—H22 | 0.9300 |
C16—C17 | 1.374 (5) | C23—H23 | 0.9300 |
C17—C18 | 1.364 (3) | C24—H24 | 0.9300 |
C18—C19 | 1.375 (3) | C25—H25 | 0.9300 |
C20—C21 | 1.511 (2) | C26—H26 | 0.9300 |
| | | |
N1···N2 | 2.241 (2) | H3···N3viii | 2.8200 |
N1···C19 | 3.306 (3) | H3···N4viii | 2.8000 |
N2···N1 | 2.241 (2) | H4···C11viii | 3.0000 |
N4···C22i | 3.435 (3) | H4A···C17ix | 3.0000 |
N1···H19 | 2.6500 | H4A···C18ix | 2.8700 |
N1···H13B | 2.6400 | H4A···H17ix | 2.5300 |
N1···H24ii | 2.8900 | H4A···H18ix | 2.2700 |
N2···H26 | 2.5800 | H4A···H2i | 2.5000 |
N3···H3iii | 2.8200 | H5···H19x | 2.4200 |
N3···H20Bi | 2.6900 | H8···C20 | 2.7100 |
N3···H2i | 2.8000 | H8···H20A | 2.2400 |
N4···H3iii | 2.8000 | H8···H16xi | 2.4800 |
N4···H2i | 2.9000 | H10···C23ii | 3.0600 |
C1···C26 | 3.585 (3) | H10···C13v | 3.0900 |
C7···C19 | 3.277 (3) | H12A···H12Axii | 2.2100 |
C7···C26 | 3.496 (3) | H12B···C16v | 3.0300 |
C19···C7 | 3.277 (3) | H12C···C23i | 3.0500 |
C19···N1 | 3.306 (3) | H13A···H15 | 2.4000 |
C20···C20i | 3.547 (3) | H13B···N1 | 2.6400 |
C22···N4i | 3.435 (3) | H13B···C10 | 2.9800 |
C26···C1 | 3.585 (3) | H13B···H19 | 2.5100 |
C26···C7 | 3.496 (3) | H15···H13A | 2.4000 |
C2···H20B | 2.8700 | H16···H8xi | 2.4800 |
C2···H17iv | 3.0800 | H17···H4Avi | 2.5300 |
C5···H24iv | 3.0000 | H17···C2iv | 3.0800 |
C7···H26 | 2.9200 | H18···H4Avi | 2.2700 |
C7···H19 | 2.9500 | H19···N1 | 2.6500 |
C8···H20A | 2.7700 | H19···C7 | 2.9500 |
C10···H13B | 2.9800 | H19···H13B | 2.5100 |
C11···H4iii | 3.0000 | H19···H5x | 2.4200 |
C13···H10v | 3.0900 | H20A···C8 | 2.7700 |
C16···H12Bv | 3.0300 | H20A···H8 | 2.2400 |
C17···H4Avi | 3.0000 | H20A···H20Bi | 2.5200 |
C18···H4Avi | 2.8700 | H20B···C2 | 2.8700 |
C19···H26 | 2.9800 | H20B···H2 | 2.4900 |
C20···H20Bi | 3.0600 | H20B···H22 | 2.4800 |
C20···H8 | 2.7100 | H20B···N3i | 2.6900 |
C20···H2 | 2.9800 | H20B···C20i | 3.0600 |
C23···H12Ci | 3.0500 | H20B···H20Ai | 2.5200 |
C23···H10vii | 3.0600 | H22···H20B | 2.4800 |
H2···C20 | 2.9800 | H24···N1vii | 2.8900 |
H2···H20B | 2.4900 | H24···C5iv | 3.0000 |
H2···N3i | 2.8000 | H26···N2 | 2.5800 |
H2···N4i | 2.9000 | H26···C7 | 2.9200 |
H2···H4Ai | 2.5000 | H26···C19 | 2.9800 |
| | | |
C6—N1—C7 | 104.67 (12) | C1—C2—H2 | 122.00 |
C1—N2—C7 | 105.93 (11) | C3—C2—H2 | 122.00 |
C1—N2—C20 | 125.09 (12) | C2—C3—H3 | 119.00 |
C7—N2—C20 | 128.96 (13) | C4—C3—H3 | 119.00 |
N4—N3—C9 | 105.52 (13) | C3—C4—H4 | 119.00 |
N3—N4—C11 | 108.75 (13) | C5—C4—H4 | 119.00 |
N3—N4—H4A | 126.00 | C4—C5—H5 | 121.00 |
C11—N4—H4A | 126.00 | C6—C5—H5 | 121.00 |
C2—C1—C6 | 122.79 (15) | C7—C8—H8 | 109.00 |
N2—C1—C2 | 131.71 (14) | C9—C8—H8 | 109.00 |
N2—C1—C6 | 105.50 (13) | C13—C8—H8 | 109.00 |
C1—C2—C3 | 116.03 (16) | C9—C10—H10 | 128.00 |
C2—C3—C4 | 122.0 (2) | C11—C10—H10 | 128.00 |
C3—C4—C5 | 121.7 (2) | C11—C12—H12A | 110.00 |
C4—C5—C6 | 117.57 (17) | C11—C12—H12B | 109.00 |
C1—C6—C5 | 119.93 (16) | C11—C12—H12C | 110.00 |
N1—C6—C1 | 110.28 (14) | H12A—C12—H12B | 109.00 |
N1—C6—C5 | 129.79 (14) | H12A—C12—H12C | 109.00 |
N2—C7—C8 | 122.51 (12) | H12B—C12—H12C | 109.00 |
N1—C7—C8 | 123.69 (13) | C8—C13—H13A | 109.00 |
N1—C7—N2 | 113.63 (14) | C8—C13—H13B | 109.00 |
C7—C8—C13 | 111.67 (13) | C14—C13—H13A | 109.00 |
C9—C8—C13 | 111.59 (13) | C14—C13—H13B | 109.00 |
C7—C8—C9 | 107.48 (12) | H13A—C13—H13B | 108.00 |
C8—C9—C10 | 129.23 (14) | C14—C15—H15 | 120.00 |
N3—C9—C8 | 119.42 (14) | C16—C15—H15 | 120.00 |
N3—C9—C10 | 111.30 (14) | C15—C16—H16 | 120.00 |
C9—C10—C11 | 104.88 (15) | C17—C16—H16 | 120.00 |
N4—C11—C12 | 117.71 (17) | C16—C17—H17 | 120.00 |
C10—C11—C12 | 132.74 (19) | C18—C17—H17 | 120.00 |
N4—C11—C10 | 109.55 (16) | C17—C18—H18 | 120.00 |
C8—C13—C14 | 113.53 (14) | C19—C18—H18 | 120.00 |
C13—C14—C19 | 121.86 (15) | C14—C19—H19 | 119.00 |
C13—C14—C15 | 120.85 (17) | C18—C19—H19 | 119.00 |
C15—C14—C19 | 117.28 (16) | N2—C20—H20A | 109.00 |
C14—C15—C16 | 120.8 (2) | N2—C20—H20B | 109.00 |
C15—C16—C17 | 120.8 (2) | C21—C20—H20A | 109.00 |
C16—C17—C18 | 119.2 (2) | C21—C20—H20B | 108.00 |
C17—C18—C19 | 120.1 (2) | H20A—C20—H20B | 108.00 |
C14—C19—C18 | 121.77 (18) | C21—C22—H22 | 120.00 |
N2—C20—C21 | 115.01 (11) | C23—C22—H22 | 120.00 |
C20—C21—C22 | 118.01 (13) | C22—C23—H23 | 120.00 |
C22—C21—C26 | 118.47 (15) | C24—C23—H23 | 120.00 |
C20—C21—C26 | 123.52 (13) | C23—C24—H24 | 120.00 |
C21—C22—C23 | 120.90 (19) | C25—C24—H24 | 120.00 |
C22—C23—C24 | 120.2 (2) | C24—C25—H25 | 120.00 |
C23—C24—C25 | 119.8 (2) | C26—C25—H25 | 120.00 |
C24—C25—C26 | 120.5 (2) | C21—C26—H26 | 120.00 |
C21—C26—C25 | 120.05 (17) | C25—C26—H26 | 120.00 |
| | | |
C6—N1—C7—N2 | 0.51 (16) | N1—C7—C8—C13 | 40.48 (19) |
C7—N1—C6—C1 | −0.08 (16) | N2—C7—C8—C9 | 92.64 (15) |
C7—N1—C6—C5 | 179.46 (16) | C7—C8—C13—C14 | 69.21 (17) |
C6—N1—C7—C8 | 175.79 (13) | C9—C8—C13—C14 | −170.47 (14) |
C1—N2—C7—C8 | −176.09 (12) | C7—C8—C9—N3 | −103.74 (16) |
C1—N2—C7—N1 | −0.75 (16) | C7—C8—C9—C10 | 73.2 (2) |
C20—N2—C7—N1 | −178.87 (12) | C13—C8—C9—N3 | 133.50 (16) |
C20—N2—C1—C2 | −1.2 (2) | C13—C8—C9—C10 | −49.5 (2) |
C20—N2—C7—C8 | 5.8 (2) | N3—C9—C10—C11 | 0.2 (2) |
C7—N2—C1—C2 | −179.46 (16) | C8—C9—C10—C11 | −176.95 (17) |
C7—N2—C20—C21 | 90.54 (18) | C9—C10—C11—C12 | 179.8 (2) |
C7—N2—C1—C6 | 0.64 (14) | C9—C10—C11—N4 | −0.4 (2) |
C20—N2—C1—C6 | 178.85 (12) | C8—C13—C14—C19 | −82.8 (2) |
C1—N2—C20—C21 | −87.25 (16) | C8—C13—C14—C15 | 96.2 (2) |
C9—N3—N4—C11 | −0.26 (18) | C13—C14—C15—C16 | −179.09 (19) |
N4—N3—C9—C8 | 177.50 (14) | C13—C14—C19—C18 | 177.99 (17) |
N4—N3—C9—C10 | 0.02 (19) | C15—C14—C19—C18 | −1.0 (3) |
N3—N4—C11—C12 | −179.76 (18) | C19—C14—C15—C16 | −0.1 (3) |
N3—N4—C11—C10 | 0.4 (2) | C14—C15—C16—C17 | 0.6 (4) |
C2—C1—C6—C5 | 0.1 (2) | C15—C16—C17—C18 | −0.1 (4) |
C6—C1—C2—C3 | 0.1 (2) | C16—C17—C18—C19 | −1.0 (3) |
N2—C1—C2—C3 | −179.82 (16) | C17—C18—C19—C14 | 1.6 (3) |
C2—C1—C6—N1 | 179.72 (14) | N2—C20—C21—C22 | 167.97 (16) |
N2—C1—C6—N1 | −0.36 (16) | N2—C20—C21—C26 | −12.8 (2) |
N2—C1—C6—C5 | −179.95 (14) | C20—C21—C22—C23 | 178.6 (2) |
C1—C2—C3—C4 | −0.1 (3) | C26—C21—C22—C23 | −0.7 (3) |
C2—C3—C4—C5 | 0.0 (3) | C20—C21—C26—C25 | −178.1 (2) |
C3—C4—C5—C6 | 0.2 (3) | C22—C21—C26—C25 | 1.1 (3) |
C4—C5—C6—N1 | −179.77 (17) | C21—C22—C23—C24 | −0.1 (4) |
C4—C5—C6—C1 | −0.3 (2) | C22—C23—C24—C25 | 0.3 (5) |
N2—C7—C8—C13 | −144.65 (13) | C23—C24—C25—C26 | 0.2 (5) |
N1—C7—C8—C9 | −82.23 (16) | C24—C25—C26—C21 | −0.9 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+1, −y, −z+2; (v) −x, −y+1, −z+2; (vi) x, y−1, z+1; (vii) x+1, y, z; (viii) x, y−1, z; (ix) x, y+1, z−1; (x) −x, −y, −z+2; (xi) −x+1, −y+1, −z+2; (xii) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···N2 | 0.93 | 2.58 | 2.900 (3) | 101 |