The molecule of the title compound, C34H32N6O2, exhibits normal geometric parameters. The two terminal phenyl rings make a dihedral angle of 69.24 (2)° with each other. The crystal packing is stabilized mainly by van der Waals interactions.
Supporting information
CCDC reference: 282222
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.151
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C10 .. 5.02 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C11 .. 6.53 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 5.69 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C30 - C31 .. 5.33 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C20 -C25 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 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
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
2,6-Dibenzyl-8 b,8c-diphenyl-2,3a,4a,6,7a,8a-
hexaazaperhydrocyclopenta[def]fluorene-4,8-dione
top
Crystal data top
C34H32N6O2 | F(000) = 1176 |
Mr = 556.66 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2525 reflections |
a = 11.7235 (9) Å | θ = 2.3–20.9° |
b = 18.3780 (13) Å | µ = 0.08 mm−1 |
c = 14.1604 (10) Å | T = 292 K |
β = 109.903 (1)° | Block, colourless |
V = 2868.7 (4) Å3 | 0.20 × 0.16 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5026 independent reflections |
Radiation source: fine-focus sealed tube | 3155 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→13 |
Tmin = 0.984, Tmax = 0.992 | k = −19→21 |
16023 measured reflections | l = −16→16 |
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)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0646P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5026 reflections | Δρmax = 0.27 e Å−3 |
379 parameters | Δρmin = −0.22 e Å−3 |
Primary atom site location: structure-invariant direct methods | |
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 | |
C1 | 1.1945 (3) | 0.15328 (17) | 0.0366 (2) | 0.0760 (9) | |
H1 | 1.1107 | 0.1479 | 0.0140 | 0.091* | |
C2 | 1.2559 (4) | 0.14027 (18) | −0.0284 (3) | 0.0859 (10) | |
H2 | 1.2141 | 0.1254 | −0.0938 | 0.103* | |
C3 | 1.3803 (4) | 0.14936 (18) | 0.0036 (3) | 0.0921 (11) | |
H3 | 1.4220 | 0.1428 | −0.0411 | 0.110* | |
C4 | 1.4424 (3) | 0.16819 (19) | 0.1019 (3) | 0.0917 (11) | |
H4 | 1.5264 | 0.1728 | 0.1249 | 0.110* | |
C5 | 1.3782 (3) | 0.17997 (16) | 0.1651 (3) | 0.0774 (9) | |
H5 | 1.4205 | 0.1924 | 0.2315 | 0.093* | |
C6 | 1.2537 (3) | 0.17419 (14) | 0.1348 (2) | 0.0620 (8) | |
C7 | 1.1857 (3) | 0.19104 (16) | 0.2064 (2) | 0.0668 (8) | |
H7A | 1.1590 | 0.1458 | 0.2276 | 0.080* | |
H7B | 1.2402 | 0.2149 | 0.2657 | 0.080* | |
C8 | 1.0141 (2) | 0.24980 (15) | 0.23005 (18) | 0.0555 (7) | |
H8A | 0.9878 | 0.2035 | 0.2484 | 0.067* | |
H8B | 1.0670 | 0.2729 | 0.2908 | 0.067* | |
C9 | 1.1198 (2) | 0.30782 (14) | 0.13393 (19) | 0.0558 (7) | |
H9A | 1.1726 | 0.3317 | 0.1940 | 0.067* | |
H9B | 1.1652 | 0.3004 | 0.0889 | 0.067* | |
C10 | 0.9529 (3) | 0.34577 (14) | −0.01628 (19) | 0.0531 (7) | |
C11 | 0.7997 (2) | 0.26564 (15) | 0.12695 (17) | 0.0498 (6) | |
C12 | 0.9319 (2) | 0.36435 (13) | 0.14111 (16) | 0.0444 (6) | |
C13 | 0.9741 (2) | 0.42287 (13) | 0.22008 (16) | 0.0461 (6) | |
C14 | 1.0578 (3) | 0.47546 (15) | 0.2178 (2) | 0.0640 (8) | |
H14 | 1.0942 | 0.4728 | 0.1689 | 0.077* | |
C15 | 1.0882 (3) | 0.53175 (16) | 0.2865 (2) | 0.0734 (9) | |
H15 | 1.1461 | 0.5658 | 0.2848 | 0.088* | |
C16 | 1.0333 (3) | 0.53716 (16) | 0.3567 (2) | 0.0728 (9) | |
H16 | 1.0519 | 0.5758 | 0.4019 | 0.087* | |
C17 | 0.9511 (3) | 0.48603 (17) | 0.3609 (2) | 0.0732 (9) | |
H17 | 0.9141 | 0.4897 | 0.4093 | 0.088* | |
C18 | 0.9226 (3) | 0.42911 (15) | 0.29410 (18) | 0.0609 (7) | |
H18 | 0.8675 | 0.3941 | 0.2988 | 0.073* | |
C19 | 0.8069 (2) | 0.37926 (13) | 0.05433 (16) | 0.0454 (6) | |
C20 | 0.7486 (2) | 0.45205 (14) | 0.05885 (17) | 0.0491 (6) | |
C21 | 0.7880 (3) | 0.51377 (16) | 0.0239 (2) | 0.0681 (8) | |
H21 | 0.8441 | 0.5103 | −0.0092 | 0.082* | |
C22 | 0.7435 (3) | 0.58077 (18) | 0.0384 (3) | 0.0847 (10) | |
H22 | 0.7734 | 0.6225 | 0.0179 | 0.102* | |
C23 | 0.6576 (3) | 0.58731 (19) | 0.0815 (3) | 0.0809 (10) | |
H23 | 0.6257 | 0.6327 | 0.0875 | 0.097* | |
C24 | 0.6188 (3) | 0.52744 (19) | 0.1157 (2) | 0.0789 (9) | |
H24 | 0.5616 | 0.5318 | 0.1476 | 0.095* | |
C25 | 0.6627 (3) | 0.45908 (16) | 0.1041 (2) | 0.0665 (8) | |
H25 | 0.6338 | 0.4180 | 0.1271 | 0.080* | |
C26 | 0.7380 (3) | 0.35391 (16) | −0.12837 (18) | 0.0615 (7) | |
H26A | 0.6828 | 0.3949 | −0.1476 | 0.074* | |
H26B | 0.7701 | 0.3454 | −0.1821 | 0.074* | |
C27 | 0.6332 (2) | 0.29800 (15) | −0.03016 (18) | 0.0572 (7) | |
H27A | 0.5980 | 0.2524 | −0.0190 | 0.069* | |
H27B | 0.5707 | 0.3350 | −0.0442 | 0.069* | |
N6 | 0.6710 (2) | 0.29022 (12) | −0.11732 (14) | 0.0574 (6) | |
C28 | 0.7342 (3) | 0.22122 (15) | −0.1186 (2) | 0.0649 (8) | |
H28A | 0.7982 | 0.2145 | −0.0544 | 0.078* | |
H28B | 0.7714 | 0.2234 | −0.1701 | 0.078* | |
C29 | 0.6485 (3) | 0.15700 (17) | −0.1388 (2) | 0.0674 (8) | |
C30 | 0.5487 (3) | 0.15394 (19) | −0.2245 (2) | 0.0872 (10) | |
H30 | 0.5333 | 0.1921 | −0.2704 | 0.105* | |
C31 | 0.4706 (4) | 0.0951 (3) | −0.2440 (3) | 0.1098 (14) | |
H31 | 0.4026 | 0.0940 | −0.3020 | 0.132* | |
C32 | 0.4946 (5) | 0.0373 (2) | −0.1759 (4) | 0.1182 (14) | |
H32 | 0.4433 | −0.0028 | −0.1884 | 0.142* | |
C33 | 0.5923 (4) | 0.0403 (2) | −0.0925 (4) | 0.1064 (13) | |
H33 | 0.6091 | 0.0020 | −0.0470 | 0.128* | |
C34 | 0.6676 (3) | 0.09933 (19) | −0.0736 (3) | 0.0857 (10) | |
H34 | 0.7342 | 0.1005 | −0.0146 | 0.103* | |
N1 | 1.08072 (19) | 0.23759 (12) | 0.16046 (15) | 0.0556 (6) | |
N2 | 1.01516 (18) | 0.35360 (11) | 0.08559 (14) | 0.0487 (5) | |
N3 | 0.90936 (18) | 0.29576 (11) | 0.18321 (13) | 0.0472 (5) | |
N4 | 0.83832 (19) | 0.37264 (11) | −0.03674 (13) | 0.0515 (5) | |
N5 | 0.73270 (18) | 0.31790 (11) | 0.06218 (14) | 0.0480 (5) | |
O1 | 0.99616 (18) | 0.32234 (11) | −0.07709 (13) | 0.0706 (6) | |
O2 | 0.76526 (16) | 0.20441 (10) | 0.13734 (12) | 0.0625 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.064 (2) | 0.087 (2) | 0.076 (2) | 0.0083 (17) | 0.0220 (17) | −0.0017 (17) |
C2 | 0.087 (3) | 0.095 (3) | 0.071 (2) | 0.012 (2) | 0.021 (2) | −0.0108 (18) |
C3 | 0.103 (3) | 0.082 (2) | 0.109 (3) | 0.012 (2) | 0.060 (3) | −0.003 (2) |
C4 | 0.066 (2) | 0.103 (3) | 0.115 (3) | −0.009 (2) | 0.043 (2) | −0.015 (2) |
C5 | 0.066 (2) | 0.077 (2) | 0.084 (2) | −0.0064 (17) | 0.0181 (19) | −0.0012 (17) |
C6 | 0.0562 (19) | 0.0592 (18) | 0.0678 (18) | 0.0015 (14) | 0.0175 (15) | 0.0028 (14) |
C7 | 0.0594 (18) | 0.077 (2) | 0.0586 (16) | 0.0022 (16) | 0.0127 (15) | 0.0116 (14) |
C8 | 0.0606 (17) | 0.0610 (16) | 0.0435 (13) | −0.0070 (14) | 0.0160 (13) | 0.0082 (12) |
C9 | 0.0509 (16) | 0.0652 (18) | 0.0553 (15) | 0.0012 (14) | 0.0232 (13) | 0.0053 (13) |
C10 | 0.0629 (18) | 0.0584 (17) | 0.0455 (15) | −0.0049 (14) | 0.0280 (14) | 0.0028 (12) |
C11 | 0.0562 (17) | 0.0583 (17) | 0.0430 (14) | −0.0087 (15) | 0.0274 (13) | −0.0029 (12) |
C12 | 0.0470 (14) | 0.0524 (15) | 0.0387 (12) | −0.0007 (12) | 0.0209 (11) | 0.0050 (11) |
C13 | 0.0505 (15) | 0.0490 (15) | 0.0389 (13) | −0.0039 (13) | 0.0155 (12) | 0.0027 (11) |
C14 | 0.0728 (19) | 0.0681 (19) | 0.0581 (16) | −0.0142 (16) | 0.0316 (15) | −0.0024 (14) |
C15 | 0.086 (2) | 0.0588 (19) | 0.075 (2) | −0.0214 (17) | 0.0262 (18) | −0.0052 (16) |
C16 | 0.081 (2) | 0.066 (2) | 0.0616 (18) | −0.0069 (18) | 0.0123 (17) | −0.0179 (15) |
C17 | 0.083 (2) | 0.088 (2) | 0.0517 (16) | −0.0107 (19) | 0.0266 (16) | −0.0171 (16) |
C18 | 0.0672 (18) | 0.0716 (19) | 0.0484 (15) | −0.0162 (15) | 0.0256 (14) | −0.0076 (14) |
C19 | 0.0483 (15) | 0.0534 (15) | 0.0393 (13) | −0.0037 (12) | 0.0210 (11) | −0.0014 (11) |
C20 | 0.0495 (15) | 0.0567 (17) | 0.0402 (13) | −0.0026 (13) | 0.0140 (12) | −0.0022 (12) |
C21 | 0.073 (2) | 0.0585 (19) | 0.085 (2) | 0.0058 (16) | 0.0419 (17) | 0.0143 (15) |
C22 | 0.075 (2) | 0.064 (2) | 0.111 (3) | −0.0015 (19) | 0.027 (2) | 0.0155 (18) |
C23 | 0.062 (2) | 0.063 (2) | 0.098 (2) | 0.0054 (18) | 0.0019 (19) | −0.0166 (18) |
C24 | 0.077 (2) | 0.076 (2) | 0.097 (2) | 0.0067 (19) | 0.0469 (19) | −0.0169 (18) |
C25 | 0.0681 (19) | 0.066 (2) | 0.0749 (19) | −0.0023 (16) | 0.0372 (16) | −0.0069 (15) |
C26 | 0.0685 (19) | 0.0737 (19) | 0.0400 (14) | 0.0047 (16) | 0.0152 (13) | 0.0064 (13) |
C27 | 0.0496 (16) | 0.0662 (17) | 0.0549 (15) | 0.0007 (13) | 0.0165 (13) | −0.0079 (13) |
N6 | 0.0614 (14) | 0.0630 (15) | 0.0450 (12) | 0.0077 (12) | 0.0146 (11) | −0.0028 (10) |
C28 | 0.0669 (19) | 0.073 (2) | 0.0549 (16) | 0.0111 (16) | 0.0204 (14) | −0.0054 (14) |
C29 | 0.069 (2) | 0.070 (2) | 0.0632 (18) | 0.0161 (17) | 0.0227 (16) | −0.0096 (16) |
C30 | 0.099 (3) | 0.075 (2) | 0.073 (2) | 0.008 (2) | 0.011 (2) | −0.0196 (17) |
C31 | 0.093 (3) | 0.115 (3) | 0.104 (3) | 0.005 (3) | 0.010 (2) | −0.045 (3) |
C32 | 0.127 (4) | 0.083 (3) | 0.152 (4) | −0.007 (3) | 0.058 (4) | −0.037 (3) |
C33 | 0.125 (4) | 0.071 (3) | 0.125 (3) | 0.002 (3) | 0.045 (3) | 0.003 (2) |
C34 | 0.091 (3) | 0.075 (2) | 0.087 (2) | 0.010 (2) | 0.025 (2) | 0.0013 (19) |
N1 | 0.0557 (14) | 0.0626 (14) | 0.0516 (12) | 0.0049 (12) | 0.0225 (11) | 0.0119 (10) |
N2 | 0.0497 (12) | 0.0603 (13) | 0.0412 (11) | 0.0027 (11) | 0.0221 (10) | 0.0066 (9) |
N3 | 0.0518 (13) | 0.0524 (12) | 0.0395 (10) | −0.0046 (11) | 0.0183 (10) | 0.0057 (9) |
N4 | 0.0528 (13) | 0.0695 (14) | 0.0365 (11) | 0.0008 (11) | 0.0207 (10) | 0.0006 (9) |
N5 | 0.0474 (12) | 0.0528 (13) | 0.0458 (11) | −0.0026 (10) | 0.0183 (10) | 0.0020 (10) |
O1 | 0.0759 (13) | 0.0972 (15) | 0.0523 (11) | 0.0040 (11) | 0.0394 (10) | −0.0062 (10) |
O2 | 0.0671 (12) | 0.0615 (12) | 0.0600 (11) | −0.0154 (10) | 0.0228 (9) | 0.0042 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.368 (4) | C17—C18 | 1.374 (4) |
C1—C6 | 1.380 (4) | C17—H17 | 0.9300 |
C1—H1 | 0.9300 | C18—H18 | 0.9300 |
C2—C3 | 1.382 (5) | C19—N5 | 1.452 (3) |
C2—H2 | 0.9300 | C19—N4 | 1.462 (3) |
C3—C4 | 1.377 (5) | C19—C20 | 1.514 (3) |
C3—H3 | 0.9300 | C20—C25 | 1.372 (4) |
C4—C5 | 1.369 (4) | C20—C21 | 1.379 (3) |
C4—H4 | 0.9300 | C21—C22 | 1.380 (4) |
C5—C6 | 1.378 (4) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—C23 | 1.349 (5) |
C6—C7 | 1.521 (4) | C22—H22 | 0.9300 |
C7—N1 | 1.457 (3) | C23—C24 | 1.342 (4) |
C7—H7A | 0.9700 | C23—H23 | 0.9300 |
C7—H7B | 0.9700 | C24—C25 | 1.389 (4) |
C8—N3 | 1.452 (3) | C24—H24 | 0.9300 |
C8—N1 | 1.468 (3) | C25—H25 | 0.9300 |
C8—H8A | 0.9700 | C26—N6 | 1.448 (3) |
C8—H8B | 0.9700 | C26—N4 | 1.465 (3) |
C9—N2 | 1.452 (3) | C26—H26A | 0.9700 |
C9—N1 | 1.461 (3) | C26—H26B | 0.9700 |
C9—H9A | 0.9700 | C27—N6 | 1.453 (3) |
C9—H9B | 0.9700 | C27—N5 | 1.471 (3) |
C10—O1 | 1.217 (3) | C27—H27A | 0.9700 |
C10—N4 | 1.367 (3) | C27—H27B | 0.9700 |
C10—N2 | 1.385 (3) | N6—C28 | 1.472 (3) |
C11—O2 | 1.221 (3) | C28—C29 | 1.513 (4) |
C11—N5 | 1.375 (3) | C28—H28A | 0.9700 |
C11—N3 | 1.378 (3) | C28—H28B | 0.9700 |
C12—N3 | 1.456 (3) | C29—C30 | 1.371 (4) |
C12—N2 | 1.460 (3) | C29—C34 | 1.372 (4) |
C12—C13 | 1.508 (3) | C30—C31 | 1.383 (5) |
C12—C19 | 1.583 (3) | C30—H30 | 0.9300 |
C13—C18 | 1.381 (3) | C31—C32 | 1.397 (6) |
C13—C14 | 1.385 (3) | C31—H31 | 0.9300 |
C14—C15 | 1.382 (4) | C32—C33 | 1.338 (6) |
C14—H14 | 0.9300 | C32—H32 | 0.9300 |
C15—C16 | 1.360 (4) | C33—C34 | 1.366 (5) |
C15—H15 | 0.9300 | C33—H33 | 0.9300 |
C16—C17 | 1.362 (4) | C34—H34 | 0.9300 |
C16—H16 | 0.9300 | | |
| | | |
C2—C1—C6 | 121.8 (3) | C25—C20—C21 | 118.7 (3) |
C2—C1—H1 | 119.1 | C25—C20—C19 | 121.1 (2) |
C6—C1—H1 | 119.1 | C21—C20—C19 | 120.0 (2) |
C1—C2—C3 | 119.7 (3) | C20—C21—C22 | 119.3 (3) |
C1—C2—H2 | 120.1 | C20—C21—H21 | 120.3 |
C3—C2—H2 | 120.1 | C22—C21—H21 | 120.3 |
C4—C3—C2 | 119.8 (3) | C23—C22—C21 | 121.7 (3) |
C4—C3—H3 | 120.1 | C23—C22—H22 | 119.1 |
C2—C3—H3 | 120.1 | C21—C22—H22 | 119.1 |
C5—C4—C3 | 118.8 (3) | C24—C23—C22 | 119.1 (3) |
C5—C4—H4 | 120.6 | C24—C23—H23 | 120.4 |
C3—C4—H4 | 120.6 | C22—C23—H23 | 120.4 |
C4—C5—C6 | 122.9 (3) | C23—C24—C25 | 121.0 (3) |
C4—C5—H5 | 118.5 | C23—C24—H24 | 119.5 |
C6—C5—H5 | 118.5 | C25—C24—H24 | 119.5 |
C5—C6—C1 | 116.8 (3) | C20—C25—C24 | 120.1 (3) |
C5—C6—C7 | 121.1 (3) | C20—C25—H25 | 120.0 |
C1—C6—C7 | 122.1 (3) | C24—C25—H25 | 120.0 |
N1—C7—C6 | 112.1 (2) | N6—C26—N4 | 113.32 (19) |
N1—C7—H7A | 109.2 | N6—C26—H26A | 108.9 |
C6—C7—H7A | 109.2 | N4—C26—H26A | 108.9 |
N1—C7—H7B | 109.2 | N6—C26—H26B | 108.9 |
C6—C7—H7B | 109.2 | N4—C26—H26B | 108.9 |
H7A—C7—H7B | 107.9 | H26A—C26—H26B | 107.7 |
N3—C8—N1 | 110.05 (18) | N6—C27—N5 | 113.7 (2) |
N3—C8—H8A | 109.6 | N6—C27—H27A | 108.8 |
N1—C8—H8A | 109.6 | N5—C27—H27A | 108.8 |
N3—C8—H8B | 109.6 | N6—C27—H27B | 108.8 |
N1—C8—H8B | 109.6 | N5—C27—H27B | 108.8 |
H8A—C8—H8B | 108.2 | H27A—C27—H27B | 107.7 |
N2—C9—N1 | 110.2 (2) | C26—N6—C27 | 110.2 (2) |
N2—C9—H9A | 109.6 | C26—N6—C28 | 113.7 (2) |
N1—C9—H9A | 109.6 | C27—N6—C28 | 113.3 (2) |
N2—C9—H9B | 109.6 | N6—C28—C29 | 111.7 (2) |
N1—C9—H9B | 109.6 | N6—C28—H28A | 109.3 |
H9A—C9—H9B | 108.1 | C29—C28—H28A | 109.3 |
O1—C10—N4 | 126.4 (2) | N6—C28—H28B | 109.3 |
O1—C10—N2 | 125.1 (3) | C29—C28—H28B | 109.3 |
N4—C10—N2 | 108.3 (2) | H28A—C28—H28B | 107.9 |
O2—C11—N5 | 126.0 (2) | C30—C29—C34 | 117.3 (3) |
O2—C11—N3 | 125.6 (2) | C30—C29—C28 | 120.7 (3) |
N5—C11—N3 | 108.3 (2) | C34—C29—C28 | 122.0 (3) |
N3—C12—N2 | 110.54 (19) | C29—C30—C31 | 121.1 (4) |
N3—C12—C13 | 111.90 (18) | C29—C30—H30 | 119.5 |
N2—C12—C13 | 112.6 (2) | C31—C30—H30 | 119.5 |
N3—C12—C19 | 102.63 (18) | C30—C31—C32 | 119.5 (4) |
N2—C12—C19 | 102.54 (17) | C30—C31—H31 | 120.3 |
C13—C12—C19 | 115.82 (19) | C32—C31—H31 | 120.3 |
C18—C13—C14 | 117.1 (2) | C33—C32—C31 | 119.3 (4) |
C18—C13—C12 | 120.3 (2) | C33—C32—H32 | 120.4 |
C14—C13—C12 | 122.4 (2) | C31—C32—H32 | 120.4 |
C15—C14—C13 | 121.4 (3) | C32—C33—C34 | 120.5 (4) |
C15—C14—H14 | 119.3 | C32—C33—H33 | 119.7 |
C13—C14—H14 | 119.3 | C34—C33—H33 | 119.7 |
C16—C15—C14 | 119.8 (3) | C33—C34—C29 | 122.3 (3) |
C16—C15—H15 | 120.1 | C33—C34—H34 | 118.8 |
C14—C15—H15 | 120.1 | C29—C34—H34 | 118.8 |
C15—C16—C17 | 120.0 (3) | C7—N1—C9 | 110.0 (2) |
C15—C16—H16 | 120.0 | C7—N1—C8 | 110.54 (19) |
C17—C16—H16 | 120.0 | C9—N1—C8 | 108.8 (2) |
C16—C17—C18 | 120.4 (3) | C10—N2—C9 | 119.5 (2) |
C16—C17—H17 | 119.8 | C10—N2—C12 | 111.3 (2) |
C18—C17—H17 | 119.8 | C9—N2—C12 | 115.90 (18) |
C17—C18—C13 | 121.3 (3) | C11—N3—C8 | 120.6 (2) |
C17—C18—H18 | 119.4 | C11—N3—C12 | 112.01 (19) |
C13—C18—H18 | 119.4 | C8—N3—C12 | 116.59 (19) |
N5—C19—N4 | 109.90 (18) | C10—N4—C19 | 111.57 (19) |
N5—C19—C20 | 113.1 (2) | C10—N4—C26 | 122.5 (2) |
N4—C19—C20 | 111.34 (19) | C19—N4—C26 | 115.7 (2) |
N5—C19—C12 | 103.10 (17) | C11—N5—C19 | 111.89 (19) |
N4—C19—C12 | 103.07 (18) | C11—N5—C27 | 121.3 (2) |
C20—C19—C12 | 115.61 (19) | C19—N5—C27 | 116.07 (19) |
| | | |
C6—C1—C2—C3 | −1.2 (5) | C31—C32—C33—C34 | 0.3 (6) |
C1—C2—C3—C4 | 3.0 (5) | C32—C33—C34—C29 | −1.1 (6) |
C2—C3—C4—C5 | −2.2 (5) | C30—C29—C34—C33 | 0.8 (5) |
C3—C4—C5—C6 | −0.3 (5) | C28—C29—C34—C33 | −178.4 (3) |
C4—C5—C6—C1 | 2.1 (5) | C6—C7—N1—C9 | −62.5 (3) |
C4—C5—C6—C7 | −177.3 (3) | C6—C7—N1—C8 | 177.3 (2) |
C2—C1—C6—C5 | −1.3 (4) | N2—C9—N1—C7 | 178.4 (2) |
C2—C1—C6—C7 | 178.0 (3) | N2—C9—N1—C8 | −60.3 (2) |
C5—C6—C7—N1 | 133.2 (3) | N3—C8—N1—C7 | −179.6 (2) |
C1—C6—C7—N1 | −46.1 (4) | N3—C8—N1—C9 | 59.5 (2) |
N3—C12—C13—C18 | −40.0 (3) | O1—C10—N2—C9 | −25.5 (4) |
N2—C12—C13—C18 | −165.3 (2) | N4—C10—N2—C9 | 158.0 (2) |
C19—C12—C13—C18 | 77.2 (3) | O1—C10—N2—C12 | −164.9 (2) |
N3—C12—C13—C14 | 145.1 (2) | N4—C10—N2—C12 | 18.6 (3) |
N2—C12—C13—C14 | 19.8 (3) | N1—C9—N2—C10 | −83.4 (3) |
C19—C12—C13—C14 | −97.8 (3) | N1—C9—N2—C12 | 54.1 (3) |
C18—C13—C14—C15 | −0.1 (4) | N3—C12—N2—C10 | 96.9 (2) |
C12—C13—C14—C15 | 175.0 (3) | C13—C12—N2—C10 | −137.1 (2) |
C13—C14—C15—C16 | −1.6 (4) | C19—C12—N2—C10 | −11.9 (2) |
C14—C15—C16—C17 | 1.9 (5) | N3—C12—N2—C9 | −44.0 (3) |
C15—C16—C17—C18 | −0.5 (5) | C13—C12—N2—C9 | 82.0 (3) |
C16—C17—C18—C13 | −1.3 (4) | C19—C12—N2—C9 | −152.84 (19) |
C14—C13—C18—C17 | 1.5 (4) | O2—C11—N3—C8 | 26.8 (4) |
C12—C13—C18—C17 | −173.7 (2) | N5—C11—N3—C8 | −157.3 (2) |
N3—C12—C19—N5 | 1.2 (2) | O2—C11—N3—C12 | 169.9 (2) |
N2—C12—C19—N5 | 115.87 (19) | N5—C11—N3—C12 | −14.2 (3) |
C13—C12—C19—N5 | −121.1 (2) | N1—C8—N3—C11 | 88.7 (3) |
N3—C12—C19—N4 | −113.23 (19) | N1—C8—N3—C12 | −52.8 (3) |
N2—C12—C19—N4 | 1.5 (2) | N2—C12—N3—C11 | −101.0 (2) |
C13—C12—C19—N4 | 124.6 (2) | C13—C12—N3—C11 | 132.5 (2) |
N3—C12—C19—C20 | 125.1 (2) | C19—C12—N3—C11 | 7.7 (2) |
N2—C12—C19—C20 | −120.2 (2) | N2—C12—N3—C8 | 43.6 (2) |
C13—C12—C19—C20 | 2.9 (3) | C13—C12—N3—C8 | −82.8 (2) |
N5—C19—C20—C25 | 23.9 (3) | C19—C12—N3—C8 | 152.36 (19) |
N4—C19—C20—C25 | 148.2 (2) | O1—C10—N4—C19 | 166.0 (2) |
C12—C19—C20—C25 | −94.7 (3) | N2—C10—N4—C19 | −17.5 (3) |
N5—C19—C20—C21 | −161.1 (2) | O1—C10—N4—C26 | 22.4 (4) |
N4—C19—C20—C21 | −36.7 (3) | N2—C10—N4—C26 | −161.1 (2) |
C12—C19—C20—C21 | 80.4 (3) | N5—C19—N4—C10 | −99.9 (2) |
C25—C20—C21—C22 | 2.2 (4) | C20—C19—N4—C10 | 134.1 (2) |
C19—C20—C21—C22 | −173.0 (2) | C12—C19—N4—C10 | 9.5 (3) |
C20—C21—C22—C23 | −3.4 (5) | N5—C19—N4—C26 | 46.5 (3) |
C21—C22—C23—C24 | 3.3 (5) | C20—C19—N4—C26 | −79.6 (3) |
C22—C23—C24—C25 | −2.2 (5) | C12—C19—N4—C26 | 155.8 (2) |
C21—C20—C25—C24 | −1.2 (4) | N6—C26—N4—C10 | 90.2 (3) |
C19—C20—C25—C24 | 174.0 (2) | N6—C26—N4—C19 | −52.1 (3) |
C23—C24—C25—C20 | 1.2 (4) | O2—C11—N5—C19 | −169.1 (2) |
N4—C26—N6—C27 | 52.3 (3) | N3—C11—N5—C19 | 15.0 (3) |
N4—C26—N6—C28 | −76.1 (3) | O2—C11—N5—C27 | −26.1 (4) |
N5—C27—N6—C26 | −51.2 (3) | N3—C11—N5—C27 | 158.0 (2) |
N5—C27—N6—C28 | 77.4 (3) | N4—C19—N5—C11 | 99.6 (2) |
C26—N6—C28—C29 | −162.6 (2) | C20—C19—N5—C11 | −135.3 (2) |
C27—N6—C28—C29 | 70.6 (3) | C12—C19—N5—C11 | −9.7 (2) |
N6—C28—C29—C30 | 57.9 (3) | N4—C19—N5—C27 | −45.4 (3) |
N6—C28—C29—C34 | −123.0 (3) | C20—C19—N5—C27 | 79.7 (2) |
C34—C29—C30—C31 | 0.2 (5) | C12—C19—N5—C27 | −154.74 (19) |
C28—C29—C30—C31 | 179.4 (3) | N6—C27—N5—C11 | −91.5 (3) |
C29—C30—C31—C32 | −0.9 (6) | N6—C27—N5—C19 | 50.0 (3) |
C30—C31—C32—C33 | 0.6 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O1i | 0.97 | 2.49 | 3.107 (3) | 122 |
Symmetry code: (i) x, −y+1/2, z+1/2. |