In the title compound, C28H31N3O, the benzimidazole group is close to perpendicular to the benzene ring. Molecules form pairs via π–π stacking interactions between benzimidazole groups.
Supporting information
CCDC reference: 646736
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.125
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.52 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
PLAT335_ALERT_2_C Large Benzene C-C Range ....... C1 -C6 0.16 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28B .. O1 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. N1 .. 2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H26B .. N2 .. 2.90 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C17 .. N1 .. 3.85 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C26 .. N2 .. 3.81 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 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
0 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 (Enraf–Nonius, 1989); cell refinement: CAD-4; data reduction: CAD-4; 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.
2,6-Di-
tert-butyl-4-{[2-(1-methyl-1
H-benzimidazol-2-
yl)phenyl]imino}cyclohexa-2,5-dien-1-one
top
Crystal data top
C28H31N3O | Z = 2 |
Mr = 425.56 | F(000) = 456 |
Triclinic, P1 | Dx = 1.170 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.691 (5) Å | Cell parameters from 24 reflections |
b = 11.963 (5) Å | θ = 10–11° |
c = 12.096 (6) Å | µ = 0.07 mm−1 |
α = 96.21 (3)° | T = 293 K |
β = 115.51 (3)° | Prism, yellow |
γ = 113.25 (3)° | 0.50 × 0.40 × 0.30 mm |
V = 1208.4 (11) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.3° |
Graphite monochromator | h = 0→12 |
θ/2θ scans | k = −14→13 |
4487 measured reflections | l = −14→13 |
4242 independent reflections | 2 standard reflections every 98 reflections |
2876 reflections with I > 2σ(I) | intensity decay: 3.7% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3 |
4242 reflections | (Δ/σ)max < 0.001 |
296 parameters | Δρmax = 0.16 e Å−3 |
3 restraints | Δρmin = −0.19 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 | |
O1 | −0.03326 (14) | −0.04042 (13) | −0.31542 (13) | 0.0797 (5) | |
N1 | 0.47392 (15) | 0.37193 (12) | 0.09031 (12) | 0.0473 (3) | |
N2 | 0.66042 (18) | 0.33419 (14) | 0.38105 (13) | 0.0579 (4) | |
N3 | 0.73751 (15) | 0.54512 (13) | 0.43274 (13) | 0.0545 (4) | |
C1 | 0.08295 (18) | 0.04591 (15) | −0.21627 (15) | 0.0472 (4) | |
C2 | 0.06385 (17) | 0.13289 (14) | −0.13355 (14) | 0.0422 (4) | |
C3 | 0.19644 (18) | 0.23636 (15) | −0.03537 (14) | 0.0455 (4) | |
H3 | 0.1856 | 0.2927 | 0.0144 | 0.055* | |
C4 | 0.35654 (17) | 0.26537 (14) | −0.00236 (14) | 0.0429 (4) | |
C5 | 0.37131 (18) | 0.16950 (15) | −0.07327 (14) | 0.0451 (4) | |
H5 | 0.4724 | 0.1809 | −0.0464 | 0.054* | |
C6 | 0.24603 (17) | 0.06602 (14) | −0.17514 (13) | 0.0418 (4) | |
C7 | 0.63108 (17) | 0.41106 (14) | 0.11918 (14) | 0.0449 (4) | |
C8 | 0.6721 (2) | 0.42301 (16) | 0.02439 (16) | 0.0542 (4) | |
H8 | 0.5944 | 0.4032 | −0.0610 | 0.065* | |
C9 | 0.8276 (2) | 0.46412 (17) | 0.05664 (19) | 0.0629 (5) | |
H9 | 0.8534 | 0.4692 | −0.0076 | 0.076* | |
C10 | 0.9442 (2) | 0.49740 (18) | 0.18314 (19) | 0.0658 (5) | |
H10 | 1.0485 | 0.5242 | 0.2044 | 0.079* | |
C11 | 0.90624 (19) | 0.49093 (17) | 0.27836 (17) | 0.0578 (5) | |
H11 | 0.9860 | 0.5153 | 0.3642 | 0.069* | |
C12 | 0.75056 (18) | 0.44847 (14) | 0.24819 (14) | 0.0467 (4) | |
C13 | 0.71215 (18) | 0.43862 (16) | 0.35187 (14) | 0.0475 (4) | |
C14 | 0.6491 (2) | 0.37265 (18) | 0.48740 (16) | 0.0580 (5) | |
C15 | 0.5988 (3) | 0.3016 (2) | 0.55784 (19) | 0.0746 (6) | |
H15 | 0.5658 | 0.2138 | 0.5362 | 0.090* | |
C16 | 0.5989 (3) | 0.3634 (3) | 0.6594 (2) | 0.0853 (7) | |
H16 | 0.5667 | 0.3171 | 0.7081 | 0.102* | |
C17 | 0.6458 (2) | 0.4934 (3) | 0.69134 (19) | 0.0850 (7) | |
H17 | 0.6429 | 0.5322 | 0.7605 | 0.102* | |
C18 | 0.6966 (2) | 0.5675 (2) | 0.62441 (18) | 0.0750 (6) | |
H18 | 0.7288 | 0.6551 | 0.6469 | 0.090* | |
C19 | 0.69724 (19) | 0.50397 (18) | 0.52088 (15) | 0.0559 (4) | |
C20 | −0.10417 (18) | 0.10083 (16) | −0.16569 (15) | 0.0489 (4) | |
C21 | −0.1942 (2) | 0.1146 (2) | −0.29663 (18) | 0.0716 (5) | |
H21A | −0.1345 | 0.2000 | −0.2950 | 0.107* | |
H21B | −0.2964 | 0.1003 | −0.3129 | 0.107* | |
H21C | −0.2083 | 0.0523 | −0.3642 | 0.107* | |
C22 | −0.1964 (2) | −0.0374 (2) | −0.1711 (2) | 0.0781 (6) | |
H22A | −0.1375 | −0.0479 | −0.0907 | 0.117* | |
H22B | −0.2114 | −0.0971 | −0.2415 | 0.117* | |
H22C | −0.2983 | −0.0537 | −0.1847 | 0.117* | |
C23 | −0.0969 (2) | 0.1928 (2) | −0.0623 (2) | 0.0823 (7) | |
H23A | −0.0400 | 0.1862 | 0.0211 | 0.124* | |
H23B | −0.2031 | 0.1703 | −0.0831 | 0.124* | |
H23C | −0.0432 | 0.2798 | −0.0601 | 0.124* | |
C24 | 0.26268 (19) | −0.03328 (15) | −0.25001 (15) | 0.0495 (4) | |
C25 | 0.1993 (3) | −0.03611 (19) | −0.39126 (17) | 0.0711 (5) | |
H25A | 0.2588 | 0.0478 | −0.3927 | 0.107* | |
H25B | 0.0890 | −0.0595 | −0.4318 | 0.107* | |
H25C | 0.2104 | −0.0984 | −0.4377 | 0.107* | |
C26 | 0.1739 (2) | −0.16689 (17) | −0.2444 (2) | 0.0682 (5) | |
H26A | 0.2204 | −0.1645 | −0.1557 | 0.102* | |
H26B | 0.1818 | −0.2289 | −0.2946 | 0.102* | |
H26C | 0.0640 | −0.1911 | −0.2794 | 0.102* | |
C27 | 0.4368 (2) | 0.0009 (2) | −0.19328 (19) | 0.0751 (6) | |
H27A | 0.4809 | 0.0012 | −0.1052 | 0.113* | |
H27B | 0.4961 | 0.0848 | −0.1948 | 0.113* | |
H27C | 0.4428 | −0.0620 | −0.2443 | 0.113* | |
C28 | 0.7840 (3) | 0.67167 (18) | 0.4190 (2) | 0.0816 (6) | |
H28A | 0.8882 | 0.7073 | 0.4303 | 0.122* | |
H28B | 0.7857 | 0.7273 | 0.4837 | 0.122* | |
H28C | 0.7091 | 0.6642 | 0.3340 | 0.122* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0448 (7) | 0.0809 (9) | 0.0732 (8) | 0.0281 (7) | 0.0125 (6) | −0.0200 (7) |
N1 | 0.0414 (7) | 0.0514 (8) | 0.0432 (7) | 0.0237 (6) | 0.0189 (6) | 0.0056 (6) |
N2 | 0.0696 (10) | 0.0595 (9) | 0.0554 (8) | 0.0389 (8) | 0.0349 (7) | 0.0165 (7) |
N3 | 0.0449 (8) | 0.0491 (8) | 0.0526 (8) | 0.0227 (6) | 0.0169 (7) | −0.0019 (6) |
C1 | 0.0415 (9) | 0.0509 (9) | 0.0452 (9) | 0.0248 (8) | 0.0191 (8) | 0.0091 (7) |
C2 | 0.0414 (9) | 0.0515 (9) | 0.0421 (8) | 0.0277 (8) | 0.0234 (7) | 0.0177 (7) |
C3 | 0.0456 (9) | 0.0530 (9) | 0.0451 (8) | 0.0290 (8) | 0.0261 (7) | 0.0109 (7) |
C4 | 0.0409 (8) | 0.0499 (9) | 0.0380 (8) | 0.0245 (7) | 0.0194 (7) | 0.0106 (7) |
C5 | 0.0400 (9) | 0.0517 (9) | 0.0455 (8) | 0.0253 (7) | 0.0225 (7) | 0.0108 (7) |
C6 | 0.0422 (9) | 0.0474 (9) | 0.0409 (8) | 0.0251 (7) | 0.0233 (7) | 0.0127 (7) |
C7 | 0.0411 (9) | 0.0400 (8) | 0.0493 (9) | 0.0204 (7) | 0.0217 (7) | 0.0055 (7) |
C8 | 0.0485 (10) | 0.0560 (10) | 0.0509 (9) | 0.0219 (8) | 0.0251 (8) | 0.0116 (8) |
C9 | 0.0623 (12) | 0.0612 (11) | 0.0724 (12) | 0.0256 (9) | 0.0450 (10) | 0.0209 (9) |
C10 | 0.0457 (10) | 0.0670 (12) | 0.0838 (14) | 0.0248 (9) | 0.0360 (10) | 0.0229 (10) |
C11 | 0.0400 (9) | 0.0585 (10) | 0.0598 (10) | 0.0214 (8) | 0.0184 (8) | 0.0123 (8) |
C12 | 0.0452 (9) | 0.0390 (8) | 0.0477 (9) | 0.0207 (7) | 0.0196 (7) | 0.0061 (7) |
C13 | 0.0406 (9) | 0.0491 (9) | 0.0417 (8) | 0.0239 (7) | 0.0137 (7) | 0.0034 (7) |
C14 | 0.0555 (11) | 0.0755 (12) | 0.0461 (9) | 0.0410 (9) | 0.0222 (8) | 0.0142 (9) |
C15 | 0.0790 (14) | 0.0957 (15) | 0.0647 (12) | 0.0526 (12) | 0.0392 (11) | 0.0326 (11) |
C16 | 0.0817 (15) | 0.130 (2) | 0.0574 (12) | 0.0613 (15) | 0.0381 (11) | 0.0308 (12) |
C17 | 0.0624 (13) | 0.135 (2) | 0.0447 (11) | 0.0491 (14) | 0.0233 (10) | 0.0045 (12) |
C18 | 0.0562 (11) | 0.0888 (14) | 0.0565 (11) | 0.0362 (10) | 0.0179 (9) | −0.0089 (10) |
C19 | 0.0408 (9) | 0.0726 (12) | 0.0407 (8) | 0.0304 (8) | 0.0126 (7) | 0.0007 (8) |
C20 | 0.0405 (9) | 0.0603 (10) | 0.0522 (9) | 0.0277 (8) | 0.0261 (7) | 0.0189 (8) |
C21 | 0.0591 (12) | 0.0973 (15) | 0.0753 (13) | 0.0513 (11) | 0.0334 (10) | 0.0419 (11) |
C22 | 0.0520 (11) | 0.0831 (14) | 0.1016 (16) | 0.0305 (10) | 0.0407 (11) | 0.0459 (12) |
C23 | 0.0528 (11) | 0.1053 (16) | 0.0862 (14) | 0.0363 (11) | 0.0425 (11) | 0.0047 (12) |
C24 | 0.0507 (9) | 0.0503 (9) | 0.0519 (9) | 0.0271 (8) | 0.0298 (8) | 0.0090 (7) |
C25 | 0.0855 (14) | 0.0717 (12) | 0.0551 (10) | 0.0356 (11) | 0.0408 (10) | 0.0113 (9) |
C26 | 0.0837 (14) | 0.0579 (11) | 0.0787 (13) | 0.0411 (10) | 0.0491 (11) | 0.0207 (9) |
C27 | 0.0608 (12) | 0.0881 (14) | 0.0772 (13) | 0.0441 (11) | 0.0361 (10) | 0.0000 (11) |
C28 | 0.0774 (14) | 0.0490 (11) | 0.0985 (15) | 0.0245 (10) | 0.0416 (12) | 0.0012 (10) |
Geometric parameters (Å, º) top
O1—C1 | 1.218 (2) | C16—C17 | 1.381 (3) |
N1—C4 | 1.293 (2) | C16—H16 | 0.930 |
N1—C7 | 1.415 (2) | C17—C18 | 1.375 (3) |
N2—C13 | 1.307 (2) | C17—H17 | 0.930 |
N2—C14 | 1.390 (2) | C18—C19 | 1.397 (2) |
N3—C13 | 1.372 (2) | C18—H18 | 0.930 |
N3—C19 | 1.380 (2) | C20—C21 | 1.527 (3) |
N3—C28 | 1.448 (3) | C20—C23 | 1.527 (3) |
C1—C6 | 1.497 (2) | C20—C22 | 1.531 (3) |
C1—C2 | 1.498 (2) | C21—H21A | 0.960 |
C2—C3 | 1.341 (2) | C21—H21B | 0.960 |
C2—C20 | 1.532 (2) | C21—H21C | 0.960 |
C3—C4 | 1.457 (2) | C22—H22A | 0.960 |
C3—H3 | 0.930 | C22—H22B | 0.960 |
C4—C5 | 1.457 (2) | C22—H22C | 0.960 |
C5—C6 | 1.336 (2) | C23—H23A | 0.960 |
C5—H5 | 0.930 | C23—H23B | 0.960 |
C6—C24 | 1.528 (2) | C23—H23C | 0.960 |
C7—C8 | 1.395 (2) | C24—C26 | 1.530 (3) |
C7—C12 | 1.395 (2) | C24—C27 | 1.531 (3) |
C8—C9 | 1.383 (3) | C24—C25 | 1.533 (3) |
C8—H8 | 0.930 | C25—H25A | 0.960 |
C9—C10 | 1.373 (3) | C25—H25B | 0.960 |
C9—H9 | 0.930 | C25—H25C | 0.960 |
C10—C11 | 1.376 (3) | C26—H26A | 0.960 |
C10—H10 | 0.930 | C26—H26B | 0.960 |
C11—C12 | 1.389 (2) | C26—H26C | 0.960 |
C11—H11 | 0.930 | C27—H27A | 0.960 |
C12—C13 | 1.481 (2) | C27—H27B | 0.960 |
C14—C15 | 1.389 (3) | C27—H27C | 0.960 |
C14—C19 | 1.393 (3) | C28—H28A | 0.960 |
C15—C16 | 1.363 (3) | C28—H28B | 0.960 |
C15—H15 | 0.930 | C28—H28C | 0.960 |
| | | |
C4—N1—C7 | 119.98 (13) | C19—C18—H18 | 121.8 |
C13—N2—C14 | 104.93 (15) | N3—C19—C14 | 105.60 (14) |
C13—N3—C19 | 106.25 (15) | N3—C19—C18 | 132.63 (19) |
C13—N3—C28 | 125.77 (16) | C14—C19—C18 | 121.76 (19) |
C19—N3—C28 | 127.78 (15) | C21—C20—C23 | 108.05 (16) |
O1—C1—C6 | 120.62 (14) | C21—C20—C22 | 109.12 (16) |
O1—C1—C2 | 120.17 (15) | C23—C20—C22 | 108.31 (16) |
C6—C1—C2 | 119.21 (14) | C21—C20—C2 | 110.19 (14) |
C3—C2—C1 | 117.59 (14) | C23—C20—C2 | 110.61 (14) |
C3—C2—C20 | 123.45 (14) | C22—C20—C2 | 110.50 (14) |
C1—C2—C20 | 118.95 (14) | C20—C21—H21A | 109.5 |
C2—C3—C4 | 123.63 (14) | C20—C21—H21B | 109.5 |
C2—C3—H3 | 118.2 | H21A—C21—H21B | 109.5 |
C4—C3—H3 | 118.2 | C20—C21—H21C | 109.5 |
N1—C4—C3 | 117.34 (14) | H21A—C21—H21C | 109.5 |
N1—C4—C5 | 125.42 (14) | H21B—C21—H21C | 109.5 |
C3—C4—C5 | 117.20 (14) | C20—C22—H22A | 109.5 |
C6—C5—C4 | 122.91 (14) | C20—C22—H22B | 109.5 |
C6—C5—H5 | 118.5 | H22A—C22—H22B | 109.5 |
C4—C5—H5 | 118.5 | C20—C22—H22C | 109.5 |
C5—C6—C1 | 118.55 (14) | H22A—C22—H22C | 109.5 |
C5—C6—C24 | 122.59 (14) | H22B—C22—H22C | 109.5 |
C1—C6—C24 | 118.85 (14) | C20—C23—H23A | 109.5 |
C8—C7—C12 | 119.12 (15) | C20—C23—H23B | 109.5 |
C8—C7—N1 | 121.92 (14) | H23A—C23—H23B | 109.5 |
C12—C7—N1 | 118.77 (14) | C20—C23—H23C | 109.5 |
C9—C8—C7 | 120.36 (16) | H23A—C23—H23C | 109.5 |
C9—C8—H8 | 119.8 | H23B—C23—H23C | 109.5 |
C7—C8—H8 | 119.8 | C6—C24—C26 | 110.35 (13) |
C10—C9—C8 | 120.29 (17) | C6—C24—C27 | 111.87 (14) |
C10—C9—H9 | 119.9 | C26—C24—C27 | 107.47 (16) |
C8—C9—H9 | 119.9 | C6—C24—C25 | 109.84 (14) |
C9—C10—C11 | 119.82 (17) | C26—C24—C25 | 110.78 (15) |
C9—C10—H10 | 120.1 | C27—C24—C25 | 106.46 (15) |
C11—C10—H10 | 120.1 | C24—C25—H25A | 109.5 |
C10—C11—C12 | 120.98 (17) | C24—C25—H25B | 109.5 |
C10—C11—H11 | 119.5 | H25A—C25—H25B | 109.5 |
C12—C11—H11 | 119.5 | C24—C25—H25C | 109.5 |
C11—C12—C7 | 119.33 (15) | H25A—C25—H25C | 109.5 |
C11—C12—C13 | 119.87 (14) | H25B—C25—H25C | 109.5 |
C7—C12—C13 | 120.76 (14) | C24—C26—H26A | 109.5 |
N2—C13—N3 | 113.29 (15) | C24—C26—H26B | 109.5 |
N2—C13—C12 | 125.49 (14) | H26A—C26—H26B | 109.5 |
N3—C13—C12 | 121.13 (15) | C24—C26—H26C | 109.5 |
C15—C14—N2 | 130.19 (18) | H26A—C26—H26C | 109.5 |
C15—C14—C19 | 119.88 (17) | H26B—C26—H26C | 109.5 |
N2—C14—C19 | 109.93 (17) | C24—C27—H27A | 109.5 |
C16—C15—C14 | 118.5 (2) | C24—C27—H27B | 109.5 |
C16—C15—H15 | 120.7 | H27A—C27—H27B | 109.5 |
C14—C15—H15 | 120.7 | C24—C27—H27C | 109.5 |
C15—C16—C17 | 121.2 (2) | H27A—C27—H27C | 109.5 |
C15—C16—H16 | 119.4 | H27B—C27—H27C | 109.5 |
C17—C16—H16 | 119.4 | N3—C28—H28A | 109.5 |
C18—C17—C16 | 122.2 (2) | N3—C28—H28B | 109.5 |
C18—C17—H17 | 118.9 | H28A—C28—H28B | 109.5 |
C16—C17—H17 | 118.9 | N3—C28—H28C | 109.5 |
C17—C18—C19 | 116.4 (2) | H28A—C28—H28C | 109.5 |
C17—C18—H18 | 121.8 | H28B—C28—H28C | 109.5 |
| | | |
O1—C1—C2—C3 | −171.37 (16) | C19—N3—C13—C12 | −177.06 (13) |
C6—C1—C2—C3 | 9.0 (2) | C28—N3—C13—C12 | 7.7 (2) |
O1—C1—C2—C20 | 7.9 (2) | C11—C12—C13—N2 | −94.7 (2) |
C6—C1—C2—C20 | −171.76 (13) | C7—C12—C13—N2 | 82.9 (2) |
C1—C2—C3—C4 | −2.4 (2) | C11—C12—C13—N3 | 81.6 (2) |
C20—C2—C3—C4 | 178.33 (14) | C7—C12—C13—N3 | −100.77 (18) |
C7—N1—C4—C3 | −174.42 (13) | C13—N2—C14—C15 | 179.09 (18) |
C7—N1—C4—C5 | 8.0 (2) | C13—N2—C14—C19 | −0.47 (18) |
C2—C3—C4—N1 | 176.42 (15) | N2—C14—C15—C16 | −179.91 (18) |
C2—C3—C4—C5 | −5.8 (2) | C19—C14—C15—C16 | −0.4 (3) |
N1—C4—C5—C6 | −174.47 (15) | C14—C15—C16—C17 | 0.8 (3) |
C3—C4—C5—C6 | 8.0 (2) | C15—C16—C17—C18 | −0.9 (3) |
C4—C5—C6—C1 | −1.6 (2) | C16—C17—C18—C19 | 0.5 (3) |
C4—C5—C6—C24 | 179.25 (14) | C13—N3—C19—C14 | 0.01 (16) |
O1—C1—C6—C5 | 173.31 (16) | C28—N3—C19—C14 | 175.09 (16) |
C2—C1—C6—C5 | −7.0 (2) | C13—N3—C19—C18 | −179.23 (17) |
O1—C1—C6—C24 | −7.5 (2) | C28—N3—C19—C18 | −4.1 (3) |
C2—C1—C6—C24 | 172.18 (13) | C15—C14—C19—N3 | −179.33 (15) |
C4—N1—C7—C8 | 54.4 (2) | N2—C14—C19—N3 | 0.28 (18) |
C4—N1—C7—C12 | −130.75 (16) | C15—C14—C19—C18 | 0.0 (3) |
C12—C7—C8—C9 | 3.8 (2) | N2—C14—C19—C18 | 179.62 (15) |
N1—C7—C8—C9 | 178.64 (15) | C17—C18—C19—N3 | 179.08 (17) |
C7—C8—C9—C10 | −2.0 (3) | C17—C18—C19—C14 | −0.1 (3) |
C8—C9—C10—C11 | −0.6 (3) | C3—C2—C20—C21 | 112.88 (18) |
C9—C10—C11—C12 | 1.4 (3) | C1—C2—C20—C21 | −66.33 (19) |
C10—C11—C12—C7 | 0.5 (2) | C3—C2—C20—C23 | −6.5 (2) |
C10—C11—C12—C13 | 178.12 (16) | C1—C2—C20—C23 | 174.26 (15) |
C8—C7—C12—C11 | −3.0 (2) | C3—C2—C20—C22 | −126.46 (18) |
N1—C7—C12—C11 | −178.01 (14) | C1—C2—C20—C22 | 54.33 (19) |
C8—C7—C12—C13 | 179.33 (14) | C5—C6—C24—C26 | 119.95 (18) |
N1—C7—C12—C13 | 4.3 (2) | C1—C6—C24—C26 | −59.24 (19) |
C14—N2—C13—N3 | 0.49 (18) | C5—C6—C24—C27 | 0.4 (2) |
C14—N2—C13—C12 | 177.06 (14) | C1—C6—C24—C27 | −178.83 (15) |
C19—N3—C13—N2 | −0.33 (18) | C5—C6—C24—C25 | −117.63 (18) |
C28—N3—C13—N2 | −175.54 (16) | C1—C6—C24—C25 | 63.18 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28B···O1i | 0.96 | 2.76 | 3.590 (3) | 145 |
C17—H17···N1ii | 0.93 | 2.96 | 3.851 (3) | 161 |
C26—H26B···N2iii | 0.96 | 2.90 | 3.805 (3) | 157 |
Symmetry codes: (i) x+1, y+1, z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z. |