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organic compounds
In the title compound, C42H38N4, the two independent molecules are each located on an inversion centre. The central C=N-N=C linkage is therefore planar.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047155/bh2059sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047155/bh2059Isup2.hkl |
CCDC reference: 629430
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.124
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
1,4-Bis[4-(di-p-tolylamino)benzyl]-2,3-diaza-1,3-butadiene top
Crystal data top
C42H38N4 | Z = 2 |
Mr = 598.76 | F(000) = 636 |
Triclinic, P1 | Dx = 1.161 Mg m−3 |
Hall symbol: -P 1 | Melting point: 498 K |
a = 11.142 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.562 (5) Å | Cell parameters from 1730 reflections |
c = 13.848 (5) Å | θ = 2.7–22.1° |
α = 72.191 (6)° | µ = 0.07 mm−1 |
β = 84.891 (7)° | T = 294 K |
γ = 68.143 (7)° | Block, colourless |
V = 1712.1 (10) Å3 | 0.32 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6005 independent reflections |
Radiation source: fine-focus sealed tube | 3032 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→8 |
Tmin = 0.979, Tmax = 0.992 | k = −14→10 |
8794 measured reflections | l = −16→15 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3 |
6005 reflections | (Δ/σ)max = 0.002 |
419 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.0943 (2) | 0.85304 (18) | 0.27873 (15) | 0.0624 (6) | |
N2 | −0.0085 (2) | 0.53336 (19) | 0.03447 (14) | 0.0673 (6) | |
N3 | 0.6145 (2) | 0.81483 (17) | 0.30673 (14) | 0.0598 (6) | |
N4 | 0.52487 (18) | 0.51356 (17) | 0.03813 (12) | 0.0521 (5) | |
C1 | 0.1452 (2) | 0.9463 (2) | 0.24908 (19) | 0.0574 (7) | |
C2 | 0.2256 (2) | 0.9553 (2) | 0.31406 (19) | 0.0626 (7) | |
H2 | 0.2475 | 0.8996 | 0.3780 | 0.075* | |
C3 | 0.2739 (3) | 1.0473 (3) | 0.2841 (2) | 0.0737 (8) | |
H3 | 0.3262 | 1.0528 | 0.3297 | 0.088* | |
C4 | 0.2474 (3) | 1.1305 (3) | 0.1900 (2) | 0.0728 (8) | |
C5 | 0.1674 (3) | 1.1198 (2) | 0.1264 (2) | 0.0782 (8) | |
H5 | 0.1475 | 1.1746 | 0.0620 | 0.094* | |
C6 | 0.1152 (3) | 1.0310 (2) | 0.1541 (2) | 0.0742 (8) | |
H6 | 0.0600 | 1.0280 | 0.1093 | 0.089* | |
C7 | 0.3024 (3) | 1.2292 (3) | 0.1589 (2) | 0.1127 (12) | |
H7A | 0.2655 | 1.2833 | 0.1991 | 0.169* | |
H7B | 0.2819 | 1.2723 | 0.0885 | 0.169* | |
H7C | 0.3946 | 1.1946 | 0.1695 | 0.169* | |
C8 | 0.0762 (2) | 0.8029 (2) | 0.38441 (18) | 0.0563 (7) | |
C9 | 0.1367 (3) | 0.6823 (3) | 0.4324 (2) | 0.0807 (9) | |
H9 | 0.1906 | 0.6328 | 0.3958 | 0.097* | |
C10 | 0.1186 (3) | 0.6340 (3) | 0.5335 (2) | 0.0818 (9) | |
H10 | 0.1589 | 0.5519 | 0.5636 | 0.098* | |
C11 | 0.0424 (2) | 0.7040 (3) | 0.59100 (19) | 0.0605 (7) | |
C12 | −0.0170 (3) | 0.8238 (2) | 0.5429 (2) | 0.0694 (8) | |
H12 | −0.0690 | 0.8734 | 0.5802 | 0.083* | |
C13 | −0.0023 (2) | 0.8739 (2) | 0.4407 (2) | 0.0655 (7) | |
H13 | −0.0454 | 0.9555 | 0.4102 | 0.079* | |
C14 | 0.0247 (3) | 0.6492 (3) | 0.70253 (18) | 0.0837 (9) | |
H14A | −0.0246 | 0.5989 | 0.7095 | 0.126* | |
H14B | −0.0203 | 0.7120 | 0.7329 | 0.126* | |
H14C | 0.1078 | 0.6020 | 0.7358 | 0.126* | |
C15 | 0.0870 (2) | 0.7910 (2) | 0.21166 (17) | 0.0539 (6) | |
C16 | −0.0052 (2) | 0.7374 (2) | 0.22579 (18) | 0.0598 (7) | |
H16 | −0.0630 | 0.7456 | 0.2782 | 0.072* | |
C17 | −0.0121 (2) | 0.6727 (2) | 0.16383 (17) | 0.0597 (7) | |
H17 | −0.0750 | 0.6386 | 0.1743 | 0.072* | |
C18 | 0.0744 (2) | 0.6579 (2) | 0.08533 (17) | 0.0527 (6) | |
C19 | 0.1641 (2) | 0.7129 (2) | 0.07096 (18) | 0.0625 (7) | |
H19 | 0.2216 | 0.7053 | 0.0183 | 0.075* | |
C20 | 0.1710 (2) | 0.7786 (2) | 0.13227 (18) | 0.0627 (7) | |
H20 | 0.2322 | 0.8148 | 0.1204 | 0.075* | |
C21 | 0.0724 (3) | 0.5850 (2) | 0.02217 (17) | 0.0603 (7) | |
H21 | 0.1323 | 0.5761 | −0.0288 | 0.072* | |
C22 | 0.6387 (2) | 0.9230 (2) | 0.28520 (17) | 0.0514 (6) | |
C23 | 0.6051 (2) | 0.9891 (2) | 0.35349 (19) | 0.0650 (7) | |
H23 | 0.5602 | 0.9658 | 0.4110 | 0.078* | |
C24 | 0.6372 (3) | 1.0890 (2) | 0.3377 (2) | 0.0708 (8) | |
H24 | 0.6139 | 1.1315 | 0.3852 | 0.085* | |
C25 | 0.7031 (3) | 1.1276 (2) | 0.2531 (2) | 0.0657 (7) | |
C26 | 0.7325 (2) | 1.0631 (2) | 0.18431 (19) | 0.0640 (7) | |
H26 | 0.7749 | 1.0881 | 0.1258 | 0.077* | |
C27 | 0.7015 (2) | 0.9625 (2) | 0.19887 (18) | 0.0562 (6) | |
H27 | 0.7230 | 0.9214 | 0.1505 | 0.067* | |
C28 | 0.7443 (3) | 1.2336 (3) | 0.2388 (2) | 0.1005 (11) | |
H28A | 0.8324 | 1.2136 | 0.2178 | 0.151* | |
H28B | 0.7372 | 1.2525 | 0.3017 | 0.151* | |
H28C | 0.6895 | 1.3018 | 0.1879 | 0.151* | |
C29 | 0.6196 (2) | 0.7434 (2) | 0.41003 (17) | 0.0521 (6) | |
C30 | 0.5241 (2) | 0.6978 (2) | 0.44663 (18) | 0.0599 (7) | |
H30 | 0.4561 | 0.7133 | 0.4037 | 0.072* | |
C31 | 0.5282 (3) | 0.6291 (2) | 0.54650 (19) | 0.0658 (7) | |
H31 | 0.4637 | 0.5979 | 0.5695 | 0.079* | |
C32 | 0.6269 (3) | 0.6060 (2) | 0.61299 (18) | 0.0599 (7) | |
C33 | 0.7219 (3) | 0.6511 (2) | 0.57467 (18) | 0.0676 (8) | |
H33 | 0.7900 | 0.6357 | 0.6175 | 0.081* | |
C34 | 0.7197 (2) | 0.7181 (2) | 0.47507 (18) | 0.0622 (7) | |
H34 | 0.7862 | 0.7466 | 0.4516 | 0.075* | |
C35 | 0.6297 (3) | 0.5339 (3) | 0.72280 (18) | 0.0907 (9) | |
H35A | 0.5715 | 0.5842 | 0.7601 | 0.136* | |
H35B | 0.7159 | 0.5037 | 0.7509 | 0.136* | |
H35C | 0.6035 | 0.4679 | 0.7273 | 0.136* | |
C36 | 0.5931 (2) | 0.7709 (2) | 0.22997 (16) | 0.0486 (6) | |
C37 | 0.5202 (2) | 0.8458 (2) | 0.14249 (16) | 0.0521 (6) | |
H37 | 0.4876 | 0.9285 | 0.1310 | 0.062* | |
C38 | 0.4959 (2) | 0.7977 (2) | 0.07229 (16) | 0.0505 (6) | |
H38 | 0.4479 | 0.8491 | 0.0135 | 0.061* | |
C39 | 0.5414 (2) | 0.6746 (2) | 0.08733 (16) | 0.0448 (6) | |
C40 | 0.6182 (2) | 0.6009 (2) | 0.17336 (17) | 0.0540 (6) | |
H40 | 0.6530 | 0.5184 | 0.1840 | 0.065* | |
C41 | 0.6436 (2) | 0.6480 (2) | 0.24279 (17) | 0.0578 (7) | |
H41 | 0.6956 | 0.5968 | 0.2997 | 0.069* | |
C42 | 0.5036 (2) | 0.6257 (2) | 0.01712 (16) | 0.0491 (6) | |
H42 | 0.4631 | 0.6774 | −0.0445 | 0.059* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0852 (16) | 0.0568 (14) | 0.0542 (14) | −0.0328 (12) | 0.0041 (11) | −0.0206 (12) |
N2 | 0.0872 (17) | 0.0707 (16) | 0.0602 (15) | −0.0396 (14) | 0.0089 (12) | −0.0302 (11) |
N3 | 0.1003 (17) | 0.0507 (13) | 0.0420 (12) | −0.0416 (12) | −0.0061 (10) | −0.0127 (11) |
N4 | 0.0698 (14) | 0.0549 (14) | 0.0428 (12) | −0.0310 (11) | −0.0020 (10) | −0.0185 (10) |
C1 | 0.0595 (18) | 0.0519 (17) | 0.0599 (17) | −0.0168 (13) | 0.0035 (13) | −0.0204 (14) |
C2 | 0.0577 (18) | 0.0662 (19) | 0.0619 (17) | −0.0198 (14) | 0.0036 (14) | −0.0202 (14) |
C3 | 0.0644 (19) | 0.091 (2) | 0.084 (2) | −0.0379 (17) | 0.0164 (16) | −0.0419 (19) |
C4 | 0.071 (2) | 0.067 (2) | 0.092 (2) | −0.0300 (16) | 0.0252 (17) | −0.0382 (19) |
C5 | 0.090 (2) | 0.0545 (19) | 0.079 (2) | −0.0235 (17) | 0.0061 (17) | −0.0086 (16) |
C6 | 0.087 (2) | 0.0601 (19) | 0.071 (2) | −0.0245 (16) | −0.0165 (15) | −0.0107 (16) |
C7 | 0.122 (3) | 0.104 (3) | 0.143 (3) | −0.073 (2) | 0.053 (2) | −0.052 (2) |
C8 | 0.0666 (18) | 0.0507 (17) | 0.0542 (16) | −0.0200 (14) | 0.0022 (13) | −0.0210 (14) |
C9 | 0.099 (2) | 0.061 (2) | 0.0598 (19) | 0.0009 (16) | 0.0001 (16) | −0.0237 (16) |
C10 | 0.103 (2) | 0.0576 (19) | 0.063 (2) | −0.0058 (16) | −0.0101 (16) | −0.0142 (16) |
C11 | 0.0657 (18) | 0.0653 (19) | 0.0578 (17) | −0.0313 (15) | 0.0001 (14) | −0.0187 (16) |
C12 | 0.079 (2) | 0.066 (2) | 0.073 (2) | −0.0302 (16) | 0.0215 (15) | −0.0357 (17) |
C13 | 0.0754 (19) | 0.0456 (16) | 0.0737 (19) | −0.0207 (14) | 0.0121 (15) | −0.0197 (15) |
C14 | 0.094 (2) | 0.105 (2) | 0.0655 (19) | −0.0550 (19) | 0.0041 (15) | −0.0215 (17) |
C15 | 0.0602 (17) | 0.0526 (16) | 0.0516 (16) | −0.0214 (13) | 0.0020 (13) | −0.0178 (13) |
C16 | 0.0656 (19) | 0.0612 (18) | 0.0570 (16) | −0.0259 (14) | 0.0117 (13) | −0.0227 (14) |
C17 | 0.0617 (18) | 0.0628 (18) | 0.0603 (17) | −0.0285 (14) | 0.0073 (13) | −0.0202 (14) |
C18 | 0.0601 (17) | 0.0530 (16) | 0.0451 (15) | −0.0207 (13) | 0.0018 (12) | −0.0145 (12) |
C19 | 0.0667 (18) | 0.0745 (19) | 0.0527 (16) | −0.0320 (15) | 0.0120 (13) | −0.0228 (15) |
C20 | 0.0637 (18) | 0.0746 (19) | 0.0643 (17) | −0.0373 (14) | 0.0105 (14) | −0.0280 (15) |
C21 | 0.073 (2) | 0.0610 (18) | 0.0504 (16) | −0.0273 (15) | 0.0092 (13) | −0.0204 (14) |
C22 | 0.0677 (18) | 0.0414 (15) | 0.0498 (15) | −0.0236 (13) | −0.0072 (13) | −0.0129 (13) |
C23 | 0.084 (2) | 0.0588 (18) | 0.0651 (17) | −0.0333 (15) | 0.0041 (14) | −0.0271 (15) |
C24 | 0.093 (2) | 0.0499 (17) | 0.081 (2) | −0.0274 (15) | −0.0111 (17) | −0.0283 (16) |
C25 | 0.079 (2) | 0.0457 (17) | 0.077 (2) | −0.0287 (14) | −0.0262 (16) | −0.0093 (15) |
C26 | 0.0745 (19) | 0.0544 (18) | 0.0639 (17) | −0.0317 (15) | −0.0123 (14) | −0.0042 (15) |
C27 | 0.0674 (18) | 0.0499 (16) | 0.0538 (16) | −0.0218 (13) | −0.0055 (13) | −0.0160 (13) |
C28 | 0.133 (3) | 0.070 (2) | 0.115 (3) | −0.059 (2) | −0.031 (2) | −0.0149 (19) |
C29 | 0.0722 (18) | 0.0494 (15) | 0.0442 (15) | −0.0306 (13) | −0.0018 (13) | −0.0157 (12) |
C30 | 0.0650 (18) | 0.0608 (17) | 0.0600 (17) | −0.0281 (14) | −0.0076 (13) | −0.0169 (14) |
C31 | 0.072 (2) | 0.0659 (19) | 0.0653 (19) | −0.0356 (15) | 0.0129 (15) | −0.0180 (15) |
C32 | 0.074 (2) | 0.0565 (17) | 0.0470 (16) | −0.0235 (15) | 0.0035 (14) | −0.0125 (13) |
C33 | 0.075 (2) | 0.083 (2) | 0.0514 (17) | −0.0380 (16) | −0.0082 (14) | −0.0150 (15) |
C34 | 0.075 (2) | 0.0741 (19) | 0.0492 (16) | −0.0431 (15) | −0.0004 (14) | −0.0141 (14) |
C35 | 0.115 (3) | 0.092 (2) | 0.0563 (18) | −0.0435 (19) | 0.0102 (16) | −0.0051 (17) |
C36 | 0.0644 (17) | 0.0454 (16) | 0.0438 (14) | −0.0260 (13) | −0.0034 (12) | −0.0150 (12) |
C37 | 0.0678 (17) | 0.0412 (15) | 0.0503 (15) | −0.0214 (12) | −0.0041 (12) | −0.0143 (13) |
C38 | 0.0625 (17) | 0.0491 (16) | 0.0414 (14) | −0.0230 (13) | −0.0069 (11) | −0.0098 (12) |
C39 | 0.0525 (15) | 0.0483 (15) | 0.0409 (14) | −0.0240 (12) | −0.0008 (11) | −0.0158 (12) |
C40 | 0.0668 (17) | 0.0398 (15) | 0.0588 (16) | −0.0200 (12) | −0.0073 (13) | −0.0160 (13) |
C41 | 0.0764 (18) | 0.0454 (16) | 0.0526 (15) | −0.0192 (13) | −0.0192 (12) | −0.0137 (13) |
C42 | 0.0587 (16) | 0.0514 (16) | 0.0431 (14) | −0.0260 (13) | 0.0025 (11) | −0.0151 (12) |
Geometric parameters (Å, º) top
N1—C15 | 1.408 (3) | C18—C21 | 1.453 (3) |
N1—C1 | 1.422 (3) | C19—C20 | 1.377 (3) |
N1—C8 | 1.434 (3) | C19—H19 | 0.9300 |
N2—C21 | 1.266 (3) | C20—H20 | 0.9300 |
N2—N2i | 1.410 (3) | C21—H21 | 0.9300 |
N3—C36 | 1.412 (3) | C22—C23 | 1.381 (3) |
N3—C22 | 1.421 (3) | C22—C27 | 1.383 (3) |
N3—C29 | 1.431 (3) | C23—C24 | 1.380 (3) |
N4—C42 | 1.281 (3) | C23—H23 | 0.9300 |
N4—N4ii | 1.415 (3) | C24—C25 | 1.382 (3) |
C1—C2 | 1.380 (3) | C24—H24 | 0.9300 |
C1—C6 | 1.389 (3) | C25—C26 | 1.375 (3) |
C2—C3 | 1.389 (3) | C25—C28 | 1.517 (3) |
C2—H2 | 0.9300 | C26—C27 | 1.383 (3) |
C3—C4 | 1.373 (4) | C26—H26 | 0.9300 |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.375 (3) | C28—H28A | 0.9600 |
C4—C7 | 1.513 (4) | C28—H28B | 0.9600 |
C5—C6 | 1.382 (3) | C28—H28C | 0.9600 |
C5—H5 | 0.9300 | C29—C34 | 1.377 (3) |
C6—H6 | 0.9300 | C29—C30 | 1.379 (3) |
C7—H7A | 0.9600 | C30—C31 | 1.382 (3) |
C7—H7B | 0.9600 | C30—H30 | 0.9300 |
C7—H7C | 0.9600 | C31—C32 | 1.386 (3) |
C8—C13 | 1.375 (3) | C31—H31 | 0.9300 |
C8—C9 | 1.376 (3) | C32—C33 | 1.372 (3) |
C9—C10 | 1.375 (3) | C32—C35 | 1.509 (3) |
C9—H9 | 0.9300 | C33—C34 | 1.376 (3) |
C10—C11 | 1.371 (3) | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.368 (3) | C35—H35A | 0.9600 |
C11—C14 | 1.515 (3) | C35—H35B | 0.9600 |
C12—C13 | 1.384 (3) | C35—H35C | 0.9600 |
C12—H12 | 0.9300 | C36—C37 | 1.386 (3) |
C13—H13 | 0.9300 | C36—C41 | 1.391 (3) |
C14—H14A | 0.9600 | C37—C38 | 1.382 (3) |
C14—H14B | 0.9600 | C37—H37 | 0.9300 |
C14—H14C | 0.9600 | C38—C39 | 1.390 (3) |
C15—C20 | 1.386 (3) | C38—H38 | 0.9300 |
C15—C16 | 1.394 (3) | C39—C40 | 1.388 (3) |
C16—C17 | 1.374 (3) | C39—C42 | 1.459 (3) |
C16—H16 | 0.9300 | C40—C41 | 1.370 (3) |
C17—C18 | 1.396 (3) | C40—H40 | 0.9300 |
C17—H17 | 0.9300 | C41—H41 | 0.9300 |
C18—C19 | 1.383 (3) | C42—H42 | 0.9300 |
C15—N1—C1 | 121.9 (2) | C15—C20—H20 | 119.9 |
C15—N1—C8 | 117.7 (2) | N2—C21—C18 | 122.0 (2) |
C1—N1—C8 | 119.0 (2) | N2—C21—H21 | 119.0 |
C21—N2—N2i | 112.1 (3) | C18—C21—H21 | 119.0 |
C36—N3—C22 | 122.70 (18) | C23—C22—C27 | 117.9 (2) |
C36—N3—C29 | 118.26 (18) | C23—C22—N3 | 120.2 (2) |
C22—N3—C29 | 118.92 (18) | C27—C22—N3 | 121.8 (2) |
C42—N4—N4ii | 112.4 (2) | C24—C23—C22 | 121.0 (2) |
C2—C1—C6 | 118.2 (2) | C24—C23—H23 | 119.5 |
C2—C1—N1 | 120.8 (2) | C22—C23—H23 | 119.5 |
C6—C1—N1 | 121.0 (2) | C23—C24—C25 | 121.6 (2) |
C1—C2—C3 | 120.1 (3) | C23—C24—H24 | 119.2 |
C1—C2—H2 | 119.9 | C25—C24—H24 | 119.2 |
C3—C2—H2 | 119.9 | C26—C25—C24 | 116.7 (2) |
C4—C3—C2 | 122.6 (3) | C26—C25—C28 | 121.8 (3) |
C4—C3—H3 | 118.7 | C24—C25—C28 | 121.5 (3) |
C2—C3—H3 | 118.7 | C25—C26—C27 | 122.5 (2) |
C3—C4—C5 | 116.3 (3) | C25—C26—H26 | 118.8 |
C3—C4—C7 | 121.5 (3) | C27—C26—H26 | 118.8 |
C5—C4—C7 | 122.1 (3) | C22—C27—C26 | 120.2 (2) |
C4—C5—C6 | 122.8 (3) | C22—C27—H27 | 119.9 |
C4—C5—H5 | 118.6 | C26—C27—H27 | 119.9 |
C6—C5—H5 | 118.6 | C25—C28—H28A | 109.5 |
C5—C6—C1 | 119.9 (3) | C25—C28—H28B | 109.5 |
C5—C6—H6 | 120.0 | H28A—C28—H28B | 109.5 |
C1—C6—H6 | 120.0 | C25—C28—H28C | 109.5 |
C4—C7—H7A | 109.5 | H28A—C28—H28C | 109.5 |
C4—C7—H7B | 109.5 | H28B—C28—H28C | 109.5 |
H7A—C7—H7B | 109.5 | C34—C29—C30 | 118.4 (2) |
C4—C7—H7C | 109.5 | C34—C29—N3 | 121.1 (2) |
H7A—C7—H7C | 109.5 | C30—C29—N3 | 120.4 (2) |
H7B—C7—H7C | 109.5 | C29—C30—C31 | 120.7 (2) |
C13—C8—C9 | 118.1 (2) | C29—C30—H30 | 119.7 |
C13—C8—N1 | 121.0 (2) | C31—C30—H30 | 119.7 |
C9—C8—N1 | 121.0 (2) | C30—C31—C32 | 121.1 (2) |
C10—C9—C8 | 121.0 (2) | C30—C31—H31 | 119.4 |
C10—C9—H9 | 119.5 | C32—C31—H31 | 119.4 |
C8—C9—H9 | 119.5 | C33—C32—C31 | 117.2 (2) |
C11—C10—C9 | 121.5 (3) | C33—C32—C35 | 121.6 (3) |
C11—C10—H10 | 119.2 | C31—C32—C35 | 121.2 (3) |
C9—C10—H10 | 119.2 | C32—C33—C34 | 122.2 (2) |
C12—C11—C10 | 117.1 (2) | C32—C33—H33 | 118.9 |
C12—C11—C14 | 122.2 (3) | C34—C33—H33 | 118.9 |
C10—C11—C14 | 120.7 (3) | C33—C34—C29 | 120.3 (2) |
C11—C12—C13 | 122.3 (2) | C33—C34—H34 | 119.8 |
C11—C12—H12 | 118.9 | C29—C34—H34 | 119.8 |
C13—C12—H12 | 118.9 | C32—C35—H35A | 109.5 |
C8—C13—C12 | 120.0 (2) | C32—C35—H35B | 109.5 |
C8—C13—H13 | 120.0 | H35A—C35—H35B | 109.5 |
C12—C13—H13 | 120.0 | C32—C35—H35C | 109.5 |
C11—C14—H14A | 109.5 | H35A—C35—H35C | 109.5 |
C11—C14—H14B | 109.5 | H35B—C35—H35C | 109.5 |
H14A—C14—H14B | 109.5 | C37—C36—C41 | 118.2 (2) |
C11—C14—H14C | 109.5 | C37—C36—N3 | 122.3 (2) |
H14A—C14—H14C | 109.5 | C41—C36—N3 | 119.5 (2) |
H14B—C14—H14C | 109.5 | C38—C37—C36 | 120.1 (2) |
C20—C15—C16 | 118.2 (2) | C38—C37—H37 | 119.9 |
C20—C15—N1 | 122.1 (2) | C36—C37—H37 | 119.9 |
C16—C15—N1 | 119.7 (2) | C37—C38—C39 | 121.7 (2) |
C17—C16—C15 | 121.2 (2) | C37—C38—H38 | 119.2 |
C17—C16—H16 | 119.4 | C39—C38—H38 | 119.2 |
C15—C16—H16 | 119.4 | C40—C39—C38 | 117.6 (2) |
C16—C17—C18 | 120.6 (2) | C40—C39—C42 | 121.8 (2) |
C16—C17—H17 | 119.7 | C38—C39—C42 | 120.5 (2) |
C18—C17—H17 | 119.7 | C41—C40—C39 | 121.0 (2) |
C19—C18—C17 | 117.7 (2) | C41—C40—H40 | 119.5 |
C19—C18—C21 | 121.0 (2) | C39—C40—H40 | 119.5 |
C17—C18—C21 | 121.3 (2) | C40—C41—C36 | 121.4 (2) |
C20—C19—C18 | 122.0 (2) | C40—C41—H41 | 119.3 |
C20—C19—H19 | 119.0 | C36—C41—H41 | 119.3 |
C18—C19—H19 | 119.0 | N4—C42—C39 | 121.7 (2) |
C19—C20—C15 | 120.2 (2) | N4—C42—H42 | 119.1 |
C19—C20—H20 | 119.9 | C39—C42—H42 | 119.1 |
C15—N1—C1—C2 | −138.5 (2) | C36—N3—C22—C23 | 152.2 (2) |
C8—N1—C1—C2 | 27.7 (3) | C29—N3—C22—C23 | −31.7 (3) |
C15—N1—C1—C6 | 41.7 (3) | C36—N3—C22—C27 | −31.1 (3) |
C8—N1—C1—C6 | −152.1 (2) | C29—N3—C22—C27 | 145.1 (2) |
C6—C1—C2—C3 | 0.2 (4) | C27—C22—C23—C24 | −2.2 (4) |
N1—C1—C2—C3 | −179.6 (2) | N3—C22—C23—C24 | 174.7 (2) |
C1—C2—C3—C4 | −1.5 (4) | C22—C23—C24—C25 | 0.5 (4) |
C2—C3—C4—C5 | 1.3 (4) | C23—C24—C25—C26 | 1.4 (4) |
C2—C3—C4—C7 | −179.4 (2) | C23—C24—C25—C28 | −176.7 (3) |
C3—C4—C5—C6 | 0.1 (4) | C24—C25—C26—C27 | −1.6 (4) |
C7—C4—C5—C6 | −179.2 (3) | C28—C25—C26—C27 | 176.6 (2) |
C4—C5—C6—C1 | −1.3 (4) | C23—C22—C27—C26 | 2.0 (4) |
C2—C1—C6—C5 | 1.1 (4) | N3—C22—C27—C26 | −174.9 (2) |
N1—C1—C6—C5 | −179.1 (2) | C25—C26—C27—C22 | −0.1 (4) |
C15—N1—C8—C13 | −134.6 (2) | C36—N3—C29—C34 | 130.3 (2) |
C1—N1—C8—C13 | 58.7 (3) | C22—N3—C29—C34 | −46.0 (3) |
C15—N1—C8—C9 | 45.3 (3) | C36—N3—C29—C30 | −49.5 (3) |
C1—N1—C8—C9 | −121.4 (3) | C22—N3—C29—C30 | 134.2 (2) |
C13—C8—C9—C10 | 0.4 (4) | C34—C29—C30—C31 | 0.5 (4) |
N1—C8—C9—C10 | −179.5 (2) | N3—C29—C30—C31 | −179.7 (2) |
C8—C9—C10—C11 | −1.6 (4) | C29—C30—C31—C32 | 1.2 (4) |
C9—C10—C11—C12 | 1.3 (4) | C30—C31—C32—C33 | −1.9 (4) |
C9—C10—C11—C14 | −179.4 (3) | C30—C31—C32—C35 | 178.3 (2) |
C10—C11—C12—C13 | 0.1 (4) | C31—C32—C33—C34 | 1.0 (4) |
C14—C11—C12—C13 | −179.1 (2) | C35—C32—C33—C34 | −179.2 (2) |
C9—C8—C13—C12 | 1.0 (4) | C32—C33—C34—C29 | 0.6 (4) |
N1—C8—C13—C12 | −179.1 (2) | C30—C29—C34—C33 | −1.4 (4) |
C11—C12—C13—C8 | −1.3 (4) | N3—C29—C34—C33 | 178.8 (2) |
C1—N1—C15—C20 | 26.9 (4) | C22—N3—C36—C37 | −39.8 (3) |
C8—N1—C15—C20 | −139.4 (2) | C29—N3—C36—C37 | 144.1 (2) |
C1—N1—C15—C16 | −154.5 (2) | C22—N3—C36—C41 | 142.0 (2) |
C8—N1—C15—C16 | 39.1 (3) | C29—N3—C36—C41 | −34.1 (3) |
C20—C15—C16—C17 | 0.8 (4) | C41—C36—C37—C38 | 2.0 (3) |
N1—C15—C16—C17 | −177.8 (2) | N3—C36—C37—C38 | −176.3 (2) |
C15—C16—C17—C18 | 0.7 (4) | C36—C37—C38—C39 | 0.9 (3) |
C16—C17—C18—C19 | −1.7 (4) | C37—C38—C39—C40 | −3.2 (3) |
C16—C17—C18—C21 | 177.0 (2) | C37—C38—C39—C42 | 173.9 (2) |
C17—C18—C19—C20 | 1.2 (4) | C38—C39—C40—C41 | 2.6 (3) |
C21—C18—C19—C20 | −177.5 (2) | C42—C39—C40—C41 | −174.4 (2) |
C18—C19—C20—C15 | 0.3 (4) | C39—C40—C41—C36 | 0.2 (4) |
C16—C15—C20—C19 | −1.3 (4) | C37—C36—C41—C40 | −2.6 (3) |
N1—C15—C20—C19 | 177.3 (2) | N3—C36—C41—C40 | 175.7 (2) |
N2i—N2—C21—C18 | −179.3 (2) | N4ii—N4—C42—C39 | 177.2 (2) |
C19—C18—C21—N2 | 179.6 (2) | C40—C39—C42—N4 | 9.4 (3) |
C17—C18—C21—N2 | 0.9 (4) | C38—C39—C42—N4 | −167.6 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
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