Crystals of 4′-(isoquinolin-4-yl)-4,2′:6′,4′′-terpyridine (iqtp), C24H16N4, grown from an ethanol solution, undergo a reversible first-order single-crystal to single-crystal phase transition at Tc in the range 273–275 K, from a disordered higher-temperature phase [form (I)] in the space group P21/c, with one single molecule in the asymmetric unit, to an ordered lower-temperature one [form (II)] in the space group P21/n, with two independent molecules in the asymmetric unit. There is a group–subgroup relationship linking (I)–(II), due to cell doubling and the disappearance of a number of symmetry operations. In addition to X-ray diffraction, the transition has been monitored by Raman spectroscopy and differential scanning calorimetry, the latter disclosing an enthalpy change of 0.72 (6) kJ mol−1. Variations of the unit-cell parameters with temperature between 170 and 293 K are presented. The evolution of diffraction spots in the vicinity of the transition temperature shows the coexistence of both phases, confirming the first-order character of the transition. Structural details of both phases are analyzed and intermolecular interactions compared in order to investigate the mechanism of the phase transition. A three-dimensional Hirshfeld surface analysis was performed to corroborate the significant changes in the intermolecular features.
Supporting information
CCDC references: 1430999; 1431000; 1431001; 1431002; 1431003
For all structures, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/6, PLATON (Spek, 2009).
Crystal data top
C24H16N4 | F(000) = 1504 |
Mr = 360.41 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 23.9426 (4) Å | Cell parameters from 4201 reflections |
b = 10.4477 (2) Å | θ = 4.1–27.1° |
c = 14.9833 (2) Å | µ = 0.08 mm−1 |
β = 106.145 (2)° | T = 170 K |
V = 3600.18 (11) Å3 | Plate, colourless |
Z = 8 | 0.28 × 0.20 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 7341 independent reflections |
Radiation source: fine-focus sealed tube | 5379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans, thick slices | θmax = 26.4°, θmin = 3.7° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | h = −29→29 |
| k = −13→13 |
58228 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
7341 reflections | Δρmax = 0.23 e Å−3 |
506 parameters | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.19118 (6) | −0.17282 (11) | 0.36046 (9) | 0.0324 (3) | |
N2A | 0.24027 (5) | 0.29269 (11) | 0.36531 (8) | 0.0231 (3) | |
N3A | 0.40890 (6) | 0.59136 (12) | 0.49767 (10) | 0.0367 (3) | |
N4A | 0.00802 (6) | 0.63685 (12) | 0.23642 (9) | 0.0345 (3) | |
C1A | 0.22822 (7) | 0.03669 (13) | 0.41093 (11) | 0.0285 (4) | |
H1A | 0.2549 | 0.0861 | 0.4543 | 0.034* | |
C2A | 0.22759 (7) | −0.09486 (14) | 0.42044 (11) | 0.0326 (4) | |
H2A | 0.2540 | −0.1315 | 0.4716 | 0.039* | |
C3A | 0.15263 (7) | −0.11612 (14) | 0.29038 (11) | 0.0311 (4) | |
H3A | 0.1262 | −0.1679 | 0.2485 | 0.037* | |
C4A | 0.14905 (7) | 0.01531 (13) | 0.27543 (11) | 0.0272 (4) | |
H4A | 0.1206 | 0.0495 | 0.2257 | 0.033* | |
C5A | 0.18852 (6) | 0.09460 (13) | 0.33585 (10) | 0.0229 (3) | |
C6A | 0.18945 (6) | 0.23607 (13) | 0.32374 (10) | 0.0221 (3) | |
C7A | 0.14007 (6) | 0.30409 (13) | 0.27578 (10) | 0.0234 (3) | |
H7A | 0.1055 | 0.2616 | 0.2475 | 0.028* | |
C8A | 0.14357 (6) | 0.43677 (13) | 0.27118 (10) | 0.0230 (3) | |
C9A | 0.19622 (7) | 0.49553 (13) | 0.31436 (10) | 0.0259 (3) | |
H9A | 0.1999 | 0.5840 | 0.3121 | 0.031* | |
C10A | 0.24350 (6) | 0.42070 (13) | 0.36101 (10) | 0.0221 (3) | |
C11A | 0.30045 (7) | 0.47911 (13) | 0.40994 (10) | 0.0232 (3) | |
C12A | 0.30632 (7) | 0.60995 (13) | 0.42646 (11) | 0.0309 (4) | |
H12A | 0.2741 | 0.6633 | 0.4083 | 0.037* | |
C13A | 0.36021 (7) | 0.66012 (14) | 0.46979 (12) | 0.0365 (4) | |
H13A | 0.3628 | 0.7479 | 0.4803 | 0.044* | |
C14A | 0.40254 (7) | 0.46571 (14) | 0.48189 (12) | 0.0355 (4) | |
H14A | 0.4356 | 0.4148 | 0.5002 | 0.043* | |
C15A | 0.35058 (7) | 0.40617 (14) | 0.44052 (10) | 0.0294 (4) | |
H15A | 0.3490 | 0.3177 | 0.4331 | 0.035* | |
C16A | 0.09222 (6) | 0.51741 (13) | 0.22409 (10) | 0.0237 (3) | |
C17A | 0.05433 (7) | 0.55740 (14) | 0.27160 (11) | 0.0310 (4) | |
H17A | 0.0604 | 0.5285 | 0.3323 | 0.037* | |
C18A | −0.00096 (7) | 0.67393 (14) | 0.14964 (11) | 0.0300 (4) | |
H18A | −0.0321 | 0.7286 | 0.1248 | 0.036* | |
C19A | 0.03373 (6) | 0.63591 (12) | 0.09163 (10) | 0.0237 (3) | |
C20A | 0.02065 (7) | 0.67344 (13) | −0.00263 (11) | 0.0291 (4) | |
H20A | −0.0118 | 0.7239 | −0.0285 | 0.035* | |
C21A | 0.05569 (7) | 0.63559 (15) | −0.05571 (11) | 0.0340 (4) | |
H21A | 0.0469 | 0.6598 | −0.1178 | 0.041* | |
C22A | 0.10503 (7) | 0.56010 (15) | −0.01680 (11) | 0.0343 (4) | |
H22A | 0.1290 | 0.5361 | −0.0533 | 0.041* | |
C23A | 0.11832 (7) | 0.52154 (13) | 0.07360 (11) | 0.0279 (4) | |
H23A | 0.1511 | 0.4715 | 0.0982 | 0.033* | |
C24A | 0.08259 (6) | 0.55725 (12) | 0.13005 (10) | 0.0222 (3) | |
N1B | 0.67935 (6) | −0.17406 (11) | 0.29159 (9) | 0.0336 (3) | |
N2B | 0.71735 (5) | 0.29314 (10) | 0.35154 (8) | 0.0228 (3) | |
N3B | 0.88527 (6) | 0.58794 (13) | 0.49516 (9) | 0.0355 (3) | |
N4B | 0.48503 (6) | 0.64291 (13) | 0.22817 (10) | 0.0376 (3) | |
C1B | 0.72404 (7) | 0.03268 (13) | 0.32625 (11) | 0.0287 (4) | |
H1B | 0.7580 | 0.0796 | 0.3491 | 0.034* | |
C2B | 0.72599 (7) | −0.09896 (14) | 0.32283 (11) | 0.0333 (4) | |
H2B | 0.7621 | −0.1383 | 0.3436 | 0.040* | |
C3B | 0.62890 (7) | −0.11321 (14) | 0.25990 (11) | 0.0315 (4) | |
H3B | 0.5958 | −0.1626 | 0.2361 | 0.038* | |
C4B | 0.62218 (7) | 0.01872 (13) | 0.25983 (10) | 0.0269 (3) | |
H4B | 0.5857 | 0.0556 | 0.2364 | 0.032* | |
C5B | 0.67081 (6) | 0.09482 (13) | 0.29531 (9) | 0.0224 (3) | |
C6B | 0.66796 (6) | 0.23710 (13) | 0.30180 (9) | 0.0217 (3) | |
C7B | 0.61830 (7) | 0.30677 (13) | 0.25839 (10) | 0.0242 (3) | |
H7B | 0.5846 | 0.2653 | 0.2251 | 0.029* | |
C8B | 0.62002 (6) | 0.43968 (13) | 0.26569 (10) | 0.0237 (3) | |
C9B | 0.67129 (7) | 0.49705 (13) | 0.31592 (10) | 0.0248 (3) | |
H9B | 0.6738 | 0.5857 | 0.3213 | 0.030* | |
C10B | 0.71900 (6) | 0.42108 (13) | 0.35833 (10) | 0.0226 (3) | |
C11B | 0.77586 (6) | 0.47815 (13) | 0.40912 (10) | 0.0236 (3) | |
C12B | 0.78198 (7) | 0.60753 (13) | 0.43131 (10) | 0.0290 (4) | |
H12B | 0.7495 | 0.6606 | 0.4179 | 0.035* | |
C13B | 0.83630 (7) | 0.65691 (14) | 0.47322 (11) | 0.0324 (4) | |
H13B | 0.8391 | 0.7438 | 0.4871 | 0.039* | |
C14B | 0.87866 (7) | 0.46363 (15) | 0.47484 (12) | 0.0372 (4) | |
H14B | 0.9118 | 0.4127 | 0.4896 | 0.045* | |
C15B | 0.82621 (7) | 0.40525 (14) | 0.43350 (11) | 0.0307 (4) | |
H15B | 0.8246 | 0.3177 | 0.4221 | 0.037* | |
C16B | 0.56953 (6) | 0.52272 (13) | 0.21852 (10) | 0.0241 (3) | |
C17B | 0.52975 (7) | 0.55993 (14) | 0.26350 (11) | 0.0319 (4) | |
H17B | 0.5334 | 0.5263 | 0.3223 | 0.038* | |
C18B | 0.48015 (7) | 0.68770 (14) | 0.14437 (11) | 0.0328 (4) | |
H18B | 0.4503 | 0.7456 | 0.1198 | 0.039* | |
C19B | 0.51697 (7) | 0.65428 (13) | 0.08900 (11) | 0.0264 (3) | |
C20B | 0.50847 (7) | 0.70174 (14) | −0.00231 (11) | 0.0330 (4) | |
H20B | 0.4780 | 0.7578 | −0.0275 | 0.040* | |
C21B | 0.54471 (8) | 0.66580 (15) | −0.05337 (12) | 0.0377 (4) | |
H21B | 0.5386 | 0.6965 | −0.1136 | 0.045* | |
C22B | 0.59130 (7) | 0.58237 (16) | −0.01546 (12) | 0.0372 (4) | |
H22B | 0.6158 | 0.5584 | −0.0510 | 0.045* | |
C23B | 0.60109 (7) | 0.53591 (14) | 0.07288 (11) | 0.0297 (4) | |
H23B | 0.6324 | 0.4816 | 0.0972 | 0.036* | |
C24B | 0.56375 (6) | 0.57011 (12) | 0.12740 (10) | 0.0231 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0380 (9) | 0.0185 (6) | 0.0414 (8) | 0.0011 (6) | 0.0121 (7) | 0.0000 (6) |
N2A | 0.0229 (7) | 0.0189 (6) | 0.0269 (7) | −0.0010 (5) | 0.0059 (5) | −0.0010 (5) |
N3A | 0.0295 (8) | 0.0263 (7) | 0.0473 (9) | −0.0024 (6) | −0.0011 (7) | −0.0016 (6) |
N4A | 0.0266 (8) | 0.0390 (8) | 0.0377 (8) | 0.0086 (6) | 0.0088 (6) | 0.0004 (6) |
C1A | 0.0252 (9) | 0.0217 (8) | 0.0366 (9) | 0.0007 (7) | 0.0055 (7) | −0.0013 (6) |
C2A | 0.0319 (9) | 0.0234 (8) | 0.0404 (9) | 0.0049 (7) | 0.0063 (8) | 0.0041 (7) |
C3A | 0.0364 (10) | 0.0226 (8) | 0.0346 (9) | −0.0053 (7) | 0.0103 (8) | −0.0057 (7) |
C4A | 0.0305 (9) | 0.0225 (7) | 0.0281 (8) | −0.0012 (7) | 0.0076 (7) | −0.0004 (6) |
C5A | 0.0228 (8) | 0.0184 (7) | 0.0294 (8) | 0.0000 (6) | 0.0104 (6) | −0.0010 (6) |
C6A | 0.0237 (8) | 0.0188 (7) | 0.0240 (7) | 0.0003 (6) | 0.0072 (6) | −0.0016 (6) |
C7A | 0.0206 (8) | 0.0223 (7) | 0.0268 (8) | −0.0024 (6) | 0.0059 (6) | −0.0011 (6) |
C8A | 0.0228 (8) | 0.0218 (7) | 0.0246 (8) | 0.0017 (6) | 0.0072 (6) | 0.0017 (6) |
C9A | 0.0258 (9) | 0.0172 (7) | 0.0328 (9) | −0.0015 (6) | 0.0050 (7) | 0.0020 (6) |
C10A | 0.0238 (8) | 0.0178 (7) | 0.0252 (8) | 0.0007 (6) | 0.0076 (6) | 0.0007 (6) |
C11A | 0.0248 (9) | 0.0200 (7) | 0.0242 (8) | −0.0003 (6) | 0.0060 (6) | 0.0024 (6) |
C12A | 0.0255 (9) | 0.0205 (8) | 0.0429 (10) | 0.0024 (7) | 0.0031 (7) | 0.0004 (7) |
C13A | 0.0321 (10) | 0.0195 (8) | 0.0519 (11) | −0.0032 (7) | 0.0015 (8) | −0.0022 (7) |
C14A | 0.0275 (9) | 0.0271 (8) | 0.0448 (10) | 0.0035 (7) | −0.0020 (8) | 0.0002 (7) |
C15A | 0.0307 (9) | 0.0182 (7) | 0.0347 (9) | 0.0008 (7) | 0.0015 (7) | 0.0000 (6) |
C16A | 0.0199 (8) | 0.0182 (7) | 0.0309 (8) | −0.0019 (6) | 0.0036 (6) | −0.0011 (6) |
C17A | 0.0279 (9) | 0.0351 (9) | 0.0286 (8) | 0.0063 (7) | 0.0056 (7) | 0.0045 (7) |
C18A | 0.0225 (9) | 0.0267 (8) | 0.0378 (9) | 0.0045 (7) | 0.0033 (7) | 0.0007 (7) |
C19A | 0.0201 (8) | 0.0166 (7) | 0.0316 (8) | −0.0026 (6) | 0.0027 (6) | −0.0021 (6) |
C20A | 0.0260 (9) | 0.0223 (7) | 0.0343 (9) | −0.0024 (7) | 0.0006 (7) | 0.0029 (6) |
C21A | 0.0378 (10) | 0.0332 (9) | 0.0286 (9) | −0.0048 (8) | 0.0053 (7) | 0.0022 (7) |
C22A | 0.0344 (10) | 0.0350 (9) | 0.0351 (9) | −0.0007 (8) | 0.0126 (8) | −0.0039 (7) |
C23A | 0.0258 (9) | 0.0245 (8) | 0.0326 (9) | 0.0030 (7) | 0.0067 (7) | 0.0000 (6) |
C24A | 0.0208 (8) | 0.0152 (7) | 0.0288 (8) | −0.0030 (6) | 0.0037 (6) | −0.0010 (6) |
N1B | 0.0415 (9) | 0.0196 (6) | 0.0399 (8) | −0.0002 (6) | 0.0116 (7) | 0.0010 (5) |
N2B | 0.0229 (7) | 0.0194 (6) | 0.0255 (7) | 0.0010 (5) | 0.0059 (5) | 0.0024 (5) |
N3B | 0.0278 (8) | 0.0339 (7) | 0.0395 (8) | −0.0034 (6) | 0.0002 (6) | −0.0050 (6) |
N4B | 0.0289 (8) | 0.0439 (8) | 0.0386 (8) | 0.0139 (7) | 0.0068 (6) | 0.0024 (6) |
C1B | 0.0268 (9) | 0.0228 (8) | 0.0349 (9) | 0.0009 (7) | 0.0060 (7) | 0.0020 (6) |
C2B | 0.0324 (10) | 0.0235 (8) | 0.0423 (10) | 0.0048 (7) | 0.0075 (8) | 0.0047 (7) |
C3B | 0.0351 (10) | 0.0237 (8) | 0.0356 (9) | −0.0069 (7) | 0.0097 (8) | −0.0039 (7) |
C4B | 0.0266 (9) | 0.0235 (8) | 0.0305 (8) | 0.0002 (6) | 0.0076 (7) | 0.0002 (6) |
C5B | 0.0276 (9) | 0.0188 (7) | 0.0219 (7) | −0.0002 (6) | 0.0085 (6) | 0.0016 (6) |
C6B | 0.0227 (8) | 0.0187 (7) | 0.0241 (7) | −0.0006 (6) | 0.0071 (6) | 0.0020 (6) |
C7B | 0.0215 (8) | 0.0211 (7) | 0.0285 (8) | −0.0023 (6) | 0.0046 (6) | 0.0000 (6) |
C8B | 0.0228 (8) | 0.0224 (7) | 0.0264 (8) | 0.0015 (6) | 0.0074 (6) | 0.0031 (6) |
C9B | 0.0255 (9) | 0.0170 (7) | 0.0309 (8) | 0.0018 (6) | 0.0062 (7) | 0.0013 (6) |
C10B | 0.0238 (8) | 0.0184 (7) | 0.0256 (8) | −0.0002 (6) | 0.0068 (6) | 0.0012 (6) |
C11B | 0.0251 (9) | 0.0216 (7) | 0.0227 (8) | 0.0002 (6) | 0.0044 (6) | 0.0030 (6) |
C12B | 0.0261 (9) | 0.0210 (8) | 0.0358 (9) | 0.0014 (7) | 0.0018 (7) | 0.0026 (6) |
C13B | 0.0343 (10) | 0.0241 (8) | 0.0351 (9) | −0.0037 (7) | 0.0037 (8) | −0.0002 (7) |
C14B | 0.0257 (9) | 0.0351 (9) | 0.0438 (10) | 0.0052 (8) | −0.0017 (8) | −0.0064 (7) |
C15B | 0.0279 (9) | 0.0229 (8) | 0.0364 (9) | 0.0020 (7) | 0.0009 (7) | −0.0037 (6) |
C16B | 0.0195 (8) | 0.0187 (7) | 0.0314 (8) | −0.0006 (6) | 0.0028 (7) | −0.0011 (6) |
C17B | 0.0288 (9) | 0.0350 (9) | 0.0309 (9) | 0.0084 (7) | 0.0067 (7) | 0.0048 (7) |
C18B | 0.0244 (9) | 0.0291 (8) | 0.0402 (10) | 0.0082 (7) | 0.0014 (7) | 0.0019 (7) |
C19B | 0.0224 (8) | 0.0191 (7) | 0.0337 (9) | −0.0024 (6) | 0.0012 (7) | 0.0005 (6) |
C20B | 0.0296 (10) | 0.0264 (8) | 0.0363 (9) | −0.0035 (7) | −0.0017 (7) | 0.0067 (7) |
C21B | 0.0411 (11) | 0.0363 (9) | 0.0327 (9) | −0.0114 (8) | 0.0054 (8) | 0.0076 (7) |
C22B | 0.0345 (10) | 0.0406 (9) | 0.0396 (10) | −0.0074 (8) | 0.0156 (8) | 0.0005 (8) |
C23B | 0.0250 (9) | 0.0274 (8) | 0.0361 (9) | −0.0015 (7) | 0.0071 (7) | 0.0016 (7) |
C24B | 0.0203 (8) | 0.0165 (7) | 0.0307 (8) | −0.0038 (6) | 0.0038 (6) | −0.0004 (6) |
Geometric parameters (Å, º) top
N1A—C3A | 1.329 (2) | N1B—C3B | 1.330 (2) |
N1A—C2A | 1.3399 (19) | N1B—C2B | 1.338 (2) |
N2A—C6A | 1.3404 (18) | N2B—C10B | 1.3402 (17) |
N2A—C10A | 1.3421 (17) | N2B—C6B | 1.3439 (17) |
N3A—C14A | 1.3350 (19) | N3B—C14B | 1.3334 (19) |
N3A—C13A | 1.334 (2) | N3B—C13B | 1.337 (2) |
N4A—C18A | 1.316 (2) | N4B—C18B | 1.314 (2) |
N4A—C17A | 1.3679 (19) | N4B—C17B | 1.3651 (19) |
C1A—C2A | 1.3822 (19) | C1B—C2B | 1.3776 (19) |
C1A—C5A | 1.393 (2) | C1B—C5B | 1.390 (2) |
C1A—H1A | 0.9300 | C1B—H1B | 0.9300 |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.3900 (19) | C3B—C4B | 1.388 (2) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.387 (2) | C4B—C5B | 1.388 (2) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.4901 (18) | C5B—C6B | 1.4925 (18) |
C6A—C7A | 1.3953 (19) | C6B—C7B | 1.3915 (19) |
C7A—C8A | 1.3917 (18) | C7B—C8B | 1.3925 (18) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.390 (2) | C8B—C9B | 1.385 (2) |
C8A—C16A | 1.495 (2) | C8B—C16B | 1.4960 (19) |
C9A—C10A | 1.393 (2) | C9B—C10B | 1.3911 (19) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.488 (2) | C10B—C11B | 1.487 (2) |
C11A—C12A | 1.3893 (19) | C11B—C15B | 1.386 (2) |
C11A—C15A | 1.388 (2) | C11B—C12B | 1.3900 (19) |
C12A—C13A | 1.377 (2) | C12B—C13B | 1.377 (2) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.375 (2) | C14B—C15B | 1.378 (2) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.365 (2) | C16B—C17B | 1.367 (2) |
C16A—C24A | 1.425 (2) | C16B—C24B | 1.422 (2) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—C19A | 1.416 (2) | C18B—C19B | 1.412 (2) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—C20A | 1.414 (2) | C19B—C20B | 1.416 (2) |
C19A—C24A | 1.4146 (19) | C19B—C24B | 1.415 (2) |
C20A—C21A | 1.365 (2) | C20B—C21B | 1.360 (2) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.405 (2) | C21B—C22B | 1.405 (2) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.363 (2) | C22B—C23B | 1.367 (2) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.410 (2) | C23B—C24B | 1.414 (2) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
| | | |
C3A—N1A—C2A | 115.99 (13) | C3B—N1B—C2B | 115.54 (13) |
C6A—N2A—C10A | 118.32 (12) | C10B—N2B—C6B | 118.65 (12) |
C14A—N3A—C13A | 115.30 (14) | C14B—N3B—C13B | 115.37 (14) |
C18A—N4A—C17A | 116.85 (13) | C18B—N4B—C17B | 116.63 (14) |
C2A—C1A—C5A | 119.37 (14) | C2B—C1B—C5B | 119.43 (14) |
C2A—C1A—H1A | 120.3 | C2B—C1B—H1B | 120.3 |
C5A—C1A—H1A | 120.3 | C5B—C1B—H1B | 120.3 |
N1A—C2A—C1A | 123.99 (15) | N1B—C2B—C1B | 124.39 (15) |
N1A—C2A—H2A | 118.0 | N1B—C2B—H2B | 117.8 |
C1A—C2A—H2A | 118.0 | C1B—C2B—H2B | 117.8 |
N1A—C3A—C4A | 124.45 (14) | N1B—C3B—C4B | 124.64 (15) |
N1A—C3A—H3A | 117.8 | N1B—C3B—H3B | 117.7 |
C4A—C3A—H3A | 117.8 | C4B—C3B—H3B | 117.7 |
C5A—C4A—C3A | 118.99 (14) | C5B—C4B—C3B | 118.96 (14) |
C5A—C4A—H4A | 120.5 | C5B—C4B—H4B | 120.5 |
C3A—C4A—H4A | 120.5 | C3B—C4B—H4B | 120.5 |
C4A—C5A—C1A | 117.12 (13) | C4B—C5B—C1B | 116.99 (13) |
C4A—C5A—C6A | 122.93 (13) | C4B—C5B—C6B | 123.16 (13) |
C1A—C5A—C6A | 119.95 (13) | C1B—C5B—C6B | 119.85 (13) |
N2A—C6A—C7A | 122.97 (12) | N2B—C6B—C7B | 122.47 (12) |
N2A—C6A—C5A | 115.06 (12) | N2B—C6B—C5B | 114.90 (12) |
C7A—C6A—C5A | 121.91 (13) | C7B—C6B—C5B | 122.62 (13) |
C6A—C7A—C8A | 118.60 (13) | C8B—C7B—C6B | 118.83 (13) |
C6A—C7A—H7A | 120.7 | C8B—C7B—H7B | 120.6 |
C8A—C7A—H7A | 120.7 | C6B—C7B—H7B | 120.6 |
C9A—C8A—C7A | 118.44 (13) | C9B—C8B—C7B | 118.45 (13) |
C9A—C8A—C16A | 119.42 (12) | C9B—C8B—C16B | 118.90 (12) |
C7A—C8A—C16A | 122.11 (13) | C7B—C8B—C16B | 122.61 (13) |
C8A—C9A—C10A | 119.41 (12) | C8B—C9B—C10B | 119.50 (13) |
C8A—C9A—H9A | 120.3 | C8B—C9B—H9B | 120.3 |
C10A—C9A—H9A | 120.3 | C10B—C9B—H9B | 120.3 |
N2A—C10A—C9A | 122.25 (13) | N2B—C10B—C9B | 122.08 (13) |
N2A—C10A—C11A | 116.25 (12) | N2B—C10B—C11B | 116.25 (12) |
C9A—C10A—C11A | 121.50 (12) | C9B—C10B—C11B | 121.57 (12) |
C12A—C11A—C15A | 116.49 (13) | C15B—C11B—C12B | 116.42 (13) |
C12A—C11A—C10A | 121.66 (13) | C15B—C11B—C10B | 121.32 (13) |
C15A—C11A—C10A | 121.84 (12) | C12B—C11B—C10B | 122.21 (13) |
C13A—C12A—C11A | 119.59 (14) | C13B—C12B—C11B | 119.79 (14) |
C13A—C12A—H12A | 120.2 | C13B—C12B—H12B | 120.1 |
C11A—C12A—H12A | 120.2 | C11B—C12B—H12B | 120.1 |
N3A—C13A—C12A | 124.44 (14) | N3B—C13B—C12B | 124.22 (14) |
N3A—C13A—H13A | 117.8 | N3B—C13B—H13B | 117.9 |
C12A—C13A—H13A | 117.8 | C12B—C13B—H13B | 117.9 |
N3A—C14A—C15A | 124.70 (15) | N3B—C14B—C15B | 124.69 (15) |
N3A—C14A—H14A | 117.7 | N3B—C14B—H14B | 117.7 |
C15A—C14A—H14A | 117.7 | C15B—C14B—H14B | 117.7 |
C14A—C15A—C11A | 119.44 (13) | C14B—C15B—C11B | 119.48 (14) |
C14A—C15A—H15A | 120.3 | C14B—C15B—H15B | 120.3 |
C11A—C15A—H15A | 120.3 | C11B—C15B—H15B | 120.3 |
C17A—C16A—C24A | 118.55 (13) | C17B—C16B—C24B | 118.62 (13) |
C17A—C16A—C8A | 120.31 (13) | C17B—C16B—C8B | 120.94 (14) |
C24A—C16A—C8A | 121.12 (13) | C24B—C16B—C8B | 120.36 (13) |
N4A—C17A—C16A | 124.73 (14) | N4B—C17B—C16B | 124.63 (15) |
N4A—C17A—H17A | 117.6 | N4B—C17B—H17B | 117.7 |
C16A—C17A—H17A | 117.6 | C16B—C17B—H17B | 117.7 |
N4A—C18A—C19A | 124.16 (14) | N4B—C18B—C19B | 124.69 (14) |
N4A—C18A—H18A | 117.9 | N4B—C18B—H18B | 117.7 |
C19A—C18A—H18A | 117.9 | C19B—C18B—H18B | 117.7 |
C20A—C19A—C24A | 119.72 (14) | C20B—C19B—C18B | 122.40 (14) |
C20A—C19A—C18A | 122.04 (14) | C20B—C19B—C24B | 119.71 (15) |
C24A—C19A—C18A | 118.24 (13) | C18B—C19B—C24B | 117.90 (14) |
C21A—C20A—C19A | 120.02 (15) | C21B—C20B—C19B | 120.29 (15) |
C21A—C20A—H20A | 120.0 | C21B—C20B—H20B | 119.9 |
C19A—C20A—H20A | 120.0 | C19B—C20B—H20B | 119.9 |
C20A—C21A—C22A | 120.18 (15) | C20B—C21B—C22B | 120.20 (15) |
C20A—C21A—H21A | 119.9 | C20B—C21B—H21B | 119.9 |
C22A—C21A—H21A | 119.9 | C22B—C21B—H21B | 119.9 |
C23A—C22A—C21A | 121.00 (15) | C23B—C22B—C21B | 120.97 (16) |
C23A—C22A—H22A | 119.5 | C23B—C22B—H22B | 119.5 |
C21A—C22A—H22A | 119.5 | C21B—C22B—H22B | 119.5 |
C22A—C23A—C24A | 120.33 (15) | C22B—C23B—C24B | 120.24 (15) |
C22A—C23A—H23A | 119.8 | C22B—C23B—H23B | 119.9 |
C24A—C23A—H23A | 119.8 | C24B—C23B—H23B | 119.9 |
C19A—C24A—C23A | 118.72 (13) | C23B—C24B—C19B | 118.58 (14) |
C19A—C24A—C16A | 117.40 (13) | C23B—C24B—C16B | 123.92 (13) |
C23A—C24A—C16A | 123.88 (13) | C19B—C24B—C16B | 117.48 (14) |
| | | |
C3A—N1A—C2A—C1A | −2.5 (2) | C3B—N1B—C2B—C1B | 2.0 (2) |
C5A—C1A—C2A—N1A | 1.0 (2) | C5B—C1B—C2B—N1B | −0.3 (2) |
C2A—N1A—C3A—C4A | 1.4 (2) | C2B—N1B—C3B—C4B | −1.7 (2) |
N1A—C3A—C4A—C5A | 1.1 (2) | N1B—C3B—C4B—C5B | −0.3 (2) |
C3A—C4A—C5A—C1A | −2.6 (2) | C3B—C4B—C5B—C1B | 2.0 (2) |
C3A—C4A—C5A—C6A | 177.86 (13) | C3B—C4B—C5B—C6B | −177.56 (13) |
C2A—C1A—C5A—C4A | 1.7 (2) | C2B—C1B—C5B—C4B | −1.8 (2) |
C2A—C1A—C5A—C6A | −178.83 (14) | C2B—C1B—C5B—C6B | 177.85 (13) |
C10A—N2A—C6A—C7A | 0.5 (2) | C10B—N2B—C6B—C7B | −1.0 (2) |
C10A—N2A—C6A—C5A | −176.93 (12) | C10B—N2B—C6B—C5B | 177.93 (12) |
C4A—C5A—C6A—N2A | −157.49 (14) | C4B—C5B—C6B—N2B | 169.54 (13) |
C1A—C5A—C6A—N2A | 23.03 (19) | C1B—C5B—C6B—N2B | −10.05 (19) |
C4A—C5A—C6A—C7A | 25.1 (2) | C4B—C5B—C6B—C7B | −11.5 (2) |
C1A—C5A—C6A—C7A | −154.42 (14) | C1B—C5B—C6B—C7B | 168.90 (14) |
N2A—C6A—C7A—C8A | −0.3 (2) | N2B—C6B—C7B—C8B | 0.9 (2) |
C5A—C6A—C7A—C8A | 176.94 (12) | C5B—C6B—C7B—C8B | −178.02 (13) |
C6A—C7A—C8A—C9A | 0.2 (2) | C6B—C7B—C8B—C9B | 0.1 (2) |
C6A—C7A—C8A—C16A | −177.83 (13) | C6B—C7B—C8B—C16B | 177.70 (13) |
C7A—C8A—C9A—C10A | −0.3 (2) | C7B—C8B—C9B—C10B | −0.8 (2) |
C16A—C8A—C9A—C10A | 177.77 (13) | C16B—C8B—C9B—C10B | −178.52 (13) |
C6A—N2A—C10A—C9A | −0.6 (2) | C6B—N2B—C10B—C9B | 0.2 (2) |
C6A—N2A—C10A—C11A | 178.72 (12) | C6B—N2B—C10B—C11B | −176.24 (12) |
C8A—C9A—C10A—N2A | 0.5 (2) | C8B—C9B—C10B—N2B | 0.7 (2) |
C8A—C9A—C10A—C11A | −178.76 (13) | C8B—C9B—C10B—C11B | 176.98 (13) |
N2A—C10A—C11A—C12A | −167.07 (13) | N2B—C10B—C11B—C15B | 10.8 (2) |
C9A—C10A—C11A—C12A | 12.3 (2) | C9B—C10B—C11B—C15B | −165.67 (14) |
N2A—C10A—C11A—C15A | 13.7 (2) | N2B—C10B—C11B—C12B | −171.84 (13) |
C9A—C10A—C11A—C15A | −166.96 (14) | C9B—C10B—C11B—C12B | 11.7 (2) |
C15A—C11A—C12A—C13A | 1.0 (2) | C15B—C11B—C12B—C13B | 1.5 (2) |
C10A—C11A—C12A—C13A | −178.26 (14) | C10B—C11B—C12B—C13B | −175.91 (14) |
C14A—N3A—C13A—C12A | −0.8 (3) | C14B—N3B—C13B—C12B | −0.9 (2) |
C11A—C12A—C13A—N3A | 0.4 (3) | C11B—C12B—C13B—N3B | −0.1 (2) |
C13A—N3A—C14A—C15A | −0.3 (2) | C13B—N3B—C14B—C15B | 0.5 (2) |
N3A—C14A—C15A—C11A | 1.7 (3) | N3B—C14B—C15B—C11B | 0.9 (3) |
C12A—C11A—C15A—C14A | −2.0 (2) | C12B—C11B—C15B—C14B | −1.9 (2) |
C10A—C11A—C15A—C14A | 177.29 (14) | C10B—C11B—C15B—C14B | 175.57 (14) |
C9A—C8A—C16A—C17A | −91.73 (18) | C9B—C8B—C16B—C17B | −89.56 (18) |
C7A—C8A—C16A—C17A | 86.31 (18) | C7B—C8B—C16B—C17B | 92.84 (18) |
C9A—C8A—C16A—C24A | 86.45 (17) | C9B—C8B—C16B—C24B | 87.09 (17) |
C7A—C8A—C16A—C24A | −95.52 (17) | C7B—C8B—C16B—C24B | −90.51 (18) |
C18A—N4A—C17A—C16A | 1.8 (2) | C18B—N4B—C17B—C16B | 1.0 (2) |
C24A—C16A—C17A—N4A | −1.9 (2) | C24B—C16B—C17B—N4B | −1.8 (2) |
C8A—C16A—C17A—N4A | 176.28 (14) | C8B—C16B—C17B—N4B | 174.94 (14) |
C17A—N4A—C18A—C19A | 0.6 (2) | C17B—N4B—C18B—C19B | 1.1 (2) |
N4A—C18A—C19A—C20A | 176.89 (14) | N4B—C18B—C19B—C20B | 177.59 (15) |
N4A—C18A—C19A—C24A | −2.7 (2) | N4B—C18B—C19B—C24B | −2.4 (2) |
C24A—C19A—C20A—C21A | −1.1 (2) | C18B—C19B—C20B—C21B | −179.31 (14) |
C18A—C19A—C20A—C21A | 179.32 (14) | C24B—C19B—C20B—C21B | 0.6 (2) |
C19A—C20A—C21A—C22A | −0.5 (2) | C19B—C20B—C21B—C22B | −0.7 (2) |
C20A—C21A—C22A—C23A | 1.1 (2) | C20B—C21B—C22B—C23B | 0.0 (2) |
C21A—C22A—C23A—C24A | −0.1 (2) | C21B—C22B—C23B—C24B | 0.8 (2) |
C20A—C19A—C24A—C23A | 2.1 (2) | C22B—C23B—C24B—C19B | −0.9 (2) |
C18A—C19A—C24A—C23A | −178.37 (13) | C22B—C23B—C24B—C16B | 177.71 (14) |
C20A—C19A—C24A—C16A | −177.16 (12) | C20B—C19B—C24B—C23B | 0.2 (2) |
C18A—C19A—C24A—C16A | 2.41 (19) | C18B—C19B—C24B—C23B | −179.88 (13) |
C22A—C23A—C24A—C19A | −1.4 (2) | C20B—C19B—C24B—C16B | −178.50 (13) |
C22A—C23A—C24A—C16A | 177.73 (14) | C18B—C19B—C24B—C16B | 1.44 (19) |
C17A—C16A—C24A—C19A | −0.3 (2) | C17B—C16B—C24B—C23B | −178.18 (14) |
C8A—C16A—C24A—C19A | −178.51 (12) | C8B—C16B—C24B—C23B | 5.1 (2) |
C17A—C16A—C24A—C23A | −179.48 (14) | C17B—C16B—C24B—C19B | 0.4 (2) |
C8A—C16A—C24A—C23A | 2.3 (2) | C8B—C16B—C24B—C19B | −176.29 (12) |
Crystal data top
C24H16N4 | F(000) = 1504 |
Mr = 360.41 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 24.0305 (5) Å | Cell parameters from 3944 reflections |
b = 10.4656 (2) Å | θ = 4.2–26.9° |
c = 15.0315 (4) Å | µ = 0.08 mm−1 |
β = 106.303 (2)° | T = 220 K |
V = 3628.32 (15) Å3 | Plate, colourless |
Z = 8 | 0.28 × 0.20 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 7397 independent reflections |
Radiation source: fine-focus sealed tube | 4918 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans, thick slices | θmax = 26.4°, θmin = 3.7° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | h = −29→30 |
| k = −13→13 |
43182 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
7397 reflections | Δρmax = 0.18 e Å−3 |
506 parameters | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.19058 (7) | −0.17106 (13) | 0.35852 (12) | 0.0429 (4) | |
N2A | 0.23894 (6) | 0.29403 (12) | 0.36421 (9) | 0.0294 (3) | |
N3A | 0.40719 (7) | 0.59122 (14) | 0.49758 (11) | 0.0467 (4) | |
N4A | 0.00763 (6) | 0.63769 (15) | 0.23531 (11) | 0.0447 (4) | |
C1A | 0.22783 (8) | 0.03767 (16) | 0.40821 (13) | 0.0383 (4) | |
H1A | 0.2550 | 0.0866 | 0.4509 | 0.046* | |
C2A | 0.22715 (8) | −0.09332 (16) | 0.41746 (14) | 0.0448 (5) | |
H2A | 0.2539 | −0.1299 | 0.4681 | 0.054* | |
C3A | 0.15164 (8) | −0.11402 (16) | 0.28954 (13) | 0.0406 (5) | |
H3A | 0.1250 | −0.1656 | 0.2482 | 0.049* | |
C4A | 0.14785 (8) | 0.01678 (15) | 0.27472 (13) | 0.0354 (4) | |
H4A | 0.1191 | 0.0508 | 0.2255 | 0.042* | |
C5A | 0.18755 (7) | 0.09617 (14) | 0.33437 (12) | 0.0295 (4) | |
C6A | 0.18837 (7) | 0.23729 (14) | 0.32244 (11) | 0.0276 (4) | |
C7A | 0.13944 (7) | 0.30580 (15) | 0.27498 (11) | 0.0305 (4) | |
H7A | 0.1050 | 0.2635 | 0.2466 | 0.037* | |
C8A | 0.14262 (7) | 0.43800 (15) | 0.27053 (11) | 0.0288 (4) | |
C9A | 0.19509 (7) | 0.49625 (15) | 0.31360 (12) | 0.0335 (4) | |
H9A | 0.1987 | 0.5846 | 0.3114 | 0.040* | |
C10A | 0.24219 (7) | 0.42179 (15) | 0.36002 (11) | 0.0287 (4) | |
C11A | 0.29908 (7) | 0.47982 (15) | 0.40907 (11) | 0.0293 (4) | |
C12A | 0.30520 (8) | 0.61018 (15) | 0.42528 (13) | 0.0395 (5) | |
H12A | 0.2732 | 0.6637 | 0.4066 | 0.047* | |
C13A | 0.35883 (8) | 0.65996 (17) | 0.46914 (14) | 0.0467 (5) | |
H13A | 0.3615 | 0.7476 | 0.4796 | 0.056* | |
C14A | 0.40057 (8) | 0.46605 (17) | 0.48205 (14) | 0.0463 (5) | |
H14A | 0.4334 | 0.4149 | 0.5009 | 0.056* | |
C15A | 0.34885 (7) | 0.40695 (16) | 0.44029 (12) | 0.0375 (4) | |
H15A | 0.3472 | 0.3187 | 0.4330 | 0.045* | |
C16A | 0.09154 (7) | 0.51847 (14) | 0.22335 (12) | 0.0296 (4) | |
C17A | 0.05369 (8) | 0.55825 (17) | 0.27032 (13) | 0.0410 (5) | |
H17A | 0.0597 | 0.5291 | 0.3307 | 0.049* | |
C18A | −0.00127 (8) | 0.67431 (16) | 0.14919 (13) | 0.0386 (4) | |
H18A | −0.0324 | 0.7285 | 0.1243 | 0.046* | |
C19A | 0.03327 (7) | 0.63711 (14) | 0.09128 (12) | 0.0303 (4) | |
C20A | 0.02039 (8) | 0.67514 (15) | −0.00261 (13) | 0.0368 (4) | |
H20A | −0.0118 | 0.7260 | −0.0283 | 0.044* | |
C21A | 0.05507 (8) | 0.63740 (17) | −0.05543 (13) | 0.0438 (5) | |
H21A | 0.0463 | 0.6619 | −0.1173 | 0.053* | |
C22A | 0.10423 (8) | 0.56136 (18) | −0.01666 (13) | 0.0437 (5) | |
H22A | 0.1280 | 0.5370 | −0.0530 | 0.052* | |
C23A | 0.11740 (8) | 0.52299 (15) | 0.07364 (13) | 0.0354 (4) | |
H23A | 0.1501 | 0.4730 | 0.0983 | 0.042* | |
C24A | 0.08189 (7) | 0.55832 (14) | 0.12990 (11) | 0.0281 (4) | |
N1B | 0.67950 (7) | −0.17189 (13) | 0.29290 (11) | 0.0440 (4) | |
N2B | 0.71755 (6) | 0.29450 (12) | 0.35139 (9) | 0.0288 (3) | |
N3B | 0.88503 (7) | 0.58812 (15) | 0.49548 (11) | 0.0456 (4) | |
N4B | 0.48598 (7) | 0.64329 (15) | 0.22815 (11) | 0.0478 (4) | |
C1B | 0.72375 (8) | 0.03412 (15) | 0.32744 (13) | 0.0385 (4) | |
H1B | 0.7577 | 0.0806 | 0.3507 | 0.046* | |
C2B | 0.72561 (8) | −0.09710 (16) | 0.32394 (14) | 0.0446 (5) | |
H2B | 0.7617 | −0.1363 | 0.3448 | 0.054* | |
C3B | 0.62927 (8) | −0.11098 (16) | 0.26073 (13) | 0.0405 (5) | |
H3B | 0.5962 | −0.1602 | 0.2369 | 0.049* | |
C4B | 0.62264 (8) | 0.02051 (15) | 0.26015 (12) | 0.0344 (4) | |
H4B | 0.5863 | 0.0572 | 0.2360 | 0.041* | |
C5B | 0.67095 (7) | 0.09673 (14) | 0.29607 (11) | 0.0280 (4) | |
C6B | 0.66826 (7) | 0.23839 (14) | 0.30195 (11) | 0.0272 (4) | |
C7B | 0.61870 (7) | 0.30870 (15) | 0.25863 (12) | 0.0308 (4) | |
H7B | 0.5849 | 0.2675 | 0.2256 | 0.037* | |
C8B | 0.62053 (7) | 0.44069 (15) | 0.26548 (11) | 0.0286 (4) | |
C9B | 0.67168 (7) | 0.49810 (15) | 0.31547 (12) | 0.0315 (4) | |
H9B | 0.6742 | 0.5866 | 0.3207 | 0.038* | |
C10B | 0.71926 (7) | 0.42229 (15) | 0.35780 (11) | 0.0284 (4) | |
C11B | 0.77599 (7) | 0.47908 (15) | 0.40870 (11) | 0.0292 (4) | |
C12B | 0.78235 (7) | 0.60767 (15) | 0.43040 (13) | 0.0380 (4) | |
H12B | 0.7501 | 0.6609 | 0.4165 | 0.046* | |
C13B | 0.83643 (8) | 0.65688 (17) | 0.47251 (13) | 0.0417 (5) | |
H13B | 0.8392 | 0.7438 | 0.4858 | 0.050* | |
C14B | 0.87813 (8) | 0.46408 (18) | 0.47542 (14) | 0.0494 (5) | |
H14B | 0.9111 | 0.4129 | 0.4907 | 0.059* | |
C15B | 0.82597 (8) | 0.40611 (16) | 0.43388 (13) | 0.0396 (5) | |
H15B | 0.8243 | 0.3186 | 0.4228 | 0.048* | |
C16B | 0.57023 (7) | 0.52386 (14) | 0.21842 (12) | 0.0301 (4) | |
C17B | 0.53079 (8) | 0.56071 (17) | 0.26339 (13) | 0.0420 (5) | |
H17B | 0.5347 | 0.5272 | 0.3221 | 0.050* | |
C18B | 0.48081 (8) | 0.68748 (17) | 0.14449 (14) | 0.0423 (5) | |
H18B | 0.4508 | 0.7447 | 0.1198 | 0.051* | |
C19B | 0.51731 (7) | 0.65467 (15) | 0.08922 (12) | 0.0334 (4) | |
C20B | 0.50860 (8) | 0.70135 (16) | −0.00185 (13) | 0.0426 (5) | |
H20B | 0.4781 | 0.7571 | −0.0270 | 0.051* | |
C21B | 0.54433 (9) | 0.66563 (18) | −0.05296 (14) | 0.0496 (5) | |
H21B | 0.5379 | 0.6957 | −0.1132 | 0.059* | |
C22B | 0.59106 (9) | 0.58307 (19) | −0.01482 (14) | 0.0483 (5) | |
H22B | 0.6155 | 0.5593 | −0.0502 | 0.058* | |
C23B | 0.60111 (8) | 0.53740 (16) | 0.07301 (13) | 0.0385 (4) | |
H23B | 0.6326 | 0.4837 | 0.0973 | 0.046* | |
C24B | 0.56412 (7) | 0.57090 (14) | 0.12752 (12) | 0.0299 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0471 (10) | 0.0243 (8) | 0.0568 (11) | 0.0011 (7) | 0.0136 (9) | 0.0002 (7) |
N2A | 0.0294 (8) | 0.0237 (7) | 0.0338 (8) | −0.0009 (6) | 0.0067 (6) | −0.0006 (6) |
N3A | 0.0357 (10) | 0.0331 (9) | 0.0611 (11) | −0.0050 (7) | −0.0032 (8) | −0.0023 (7) |
N4A | 0.0321 (9) | 0.0538 (10) | 0.0466 (10) | 0.0134 (7) | 0.0087 (8) | 0.0008 (8) |
C1A | 0.0334 (10) | 0.0277 (10) | 0.0500 (12) | 0.0017 (8) | 0.0052 (9) | −0.0016 (8) |
C2A | 0.0420 (12) | 0.0287 (10) | 0.0588 (13) | 0.0064 (8) | 0.0063 (10) | 0.0039 (9) |
C3A | 0.0485 (12) | 0.0286 (10) | 0.0450 (12) | −0.0074 (8) | 0.0136 (10) | −0.0059 (8) |
C4A | 0.0394 (11) | 0.0284 (9) | 0.0370 (11) | −0.0017 (8) | 0.0083 (9) | −0.0012 (8) |
C5A | 0.0274 (9) | 0.0242 (9) | 0.0385 (10) | −0.0004 (7) | 0.0119 (8) | −0.0004 (7) |
C6A | 0.0268 (9) | 0.0235 (8) | 0.0319 (9) | −0.0006 (7) | 0.0073 (7) | −0.0021 (7) |
C7A | 0.0268 (10) | 0.0281 (9) | 0.0350 (10) | −0.0036 (7) | 0.0061 (8) | −0.0025 (7) |
C8A | 0.0274 (10) | 0.0267 (9) | 0.0314 (9) | 0.0020 (7) | 0.0067 (7) | 0.0016 (7) |
C9A | 0.0324 (10) | 0.0214 (9) | 0.0441 (11) | −0.0005 (7) | 0.0066 (8) | 0.0027 (7) |
C10A | 0.0298 (10) | 0.0229 (8) | 0.0323 (10) | −0.0005 (7) | 0.0071 (8) | 0.0005 (7) |
C11A | 0.0295 (10) | 0.0252 (9) | 0.0317 (10) | −0.0010 (7) | 0.0062 (8) | 0.0015 (7) |
C12A | 0.0316 (11) | 0.0257 (9) | 0.0549 (12) | 0.0019 (7) | 0.0017 (9) | −0.0005 (8) |
C13A | 0.0407 (12) | 0.0253 (10) | 0.0652 (14) | −0.0048 (8) | 0.0000 (10) | −0.0035 (9) |
C14A | 0.0341 (11) | 0.0337 (11) | 0.0602 (14) | 0.0053 (8) | −0.0048 (10) | −0.0005 (9) |
C15A | 0.0359 (11) | 0.0235 (9) | 0.0454 (11) | 0.0011 (8) | −0.0011 (9) | 0.0011 (8) |
C16A | 0.0251 (9) | 0.0221 (8) | 0.0386 (10) | −0.0006 (7) | 0.0039 (8) | 0.0001 (7) |
C17A | 0.0365 (11) | 0.0472 (11) | 0.0382 (11) | 0.0092 (9) | 0.0088 (9) | 0.0058 (9) |
C18A | 0.0287 (10) | 0.0351 (10) | 0.0467 (12) | 0.0072 (8) | 0.0023 (9) | 0.0000 (8) |
C19A | 0.0267 (9) | 0.0207 (8) | 0.0392 (10) | −0.0020 (7) | 0.0021 (8) | −0.0005 (7) |
C20A | 0.0320 (10) | 0.0281 (9) | 0.0429 (11) | −0.0017 (7) | −0.0018 (8) | 0.0038 (8) |
C21A | 0.0502 (13) | 0.0425 (11) | 0.0345 (11) | −0.0053 (9) | 0.0048 (9) | 0.0044 (9) |
C22A | 0.0448 (12) | 0.0457 (11) | 0.0420 (12) | −0.0009 (9) | 0.0145 (10) | −0.0036 (9) |
C23A | 0.0309 (10) | 0.0316 (9) | 0.0416 (11) | 0.0032 (7) | 0.0069 (8) | −0.0001 (8) |
C24A | 0.0249 (9) | 0.0181 (8) | 0.0377 (10) | −0.0028 (6) | 0.0029 (8) | −0.0010 (7) |
N1B | 0.0496 (11) | 0.0251 (8) | 0.0561 (11) | −0.0003 (7) | 0.0129 (9) | 0.0015 (7) |
N2B | 0.0278 (8) | 0.0240 (7) | 0.0324 (8) | −0.0003 (6) | 0.0050 (6) | 0.0025 (6) |
N3B | 0.0341 (10) | 0.0445 (10) | 0.0501 (10) | −0.0050 (7) | −0.0015 (8) | −0.0064 (8) |
N4B | 0.0359 (10) | 0.0570 (10) | 0.0477 (11) | 0.0186 (8) | 0.0073 (8) | 0.0019 (8) |
C1B | 0.0337 (11) | 0.0281 (10) | 0.0502 (12) | 0.0007 (8) | 0.0058 (9) | 0.0012 (8) |
C2B | 0.0429 (12) | 0.0298 (10) | 0.0583 (13) | 0.0060 (8) | 0.0095 (10) | 0.0060 (9) |
C3B | 0.0439 (12) | 0.0292 (10) | 0.0476 (12) | −0.0086 (8) | 0.0114 (9) | −0.0045 (8) |
C4B | 0.0336 (10) | 0.0289 (9) | 0.0390 (11) | 0.0007 (7) | 0.0075 (8) | −0.0018 (8) |
C5B | 0.0325 (10) | 0.0234 (9) | 0.0277 (9) | 0.0002 (7) | 0.0079 (7) | 0.0030 (7) |
C6B | 0.0280 (9) | 0.0245 (9) | 0.0286 (9) | 0.0000 (7) | 0.0074 (7) | 0.0027 (7) |
C7B | 0.0278 (10) | 0.0257 (9) | 0.0357 (10) | −0.0023 (7) | 0.0035 (8) | 0.0014 (7) |
C8B | 0.0254 (9) | 0.0274 (9) | 0.0318 (10) | 0.0019 (7) | 0.0062 (7) | 0.0035 (7) |
C9B | 0.0313 (10) | 0.0209 (8) | 0.0397 (11) | 0.0017 (7) | 0.0057 (8) | 0.0026 (7) |
C10B | 0.0286 (10) | 0.0238 (9) | 0.0315 (9) | 0.0002 (7) | 0.0060 (7) | 0.0019 (7) |
C11B | 0.0281 (10) | 0.0264 (9) | 0.0299 (9) | −0.0009 (7) | 0.0029 (8) | 0.0024 (7) |
C12B | 0.0318 (11) | 0.0268 (10) | 0.0483 (12) | 0.0003 (7) | −0.0006 (9) | 0.0018 (8) |
C13B | 0.0410 (12) | 0.0305 (10) | 0.0471 (12) | −0.0060 (8) | 0.0017 (9) | −0.0016 (8) |
C14B | 0.0330 (11) | 0.0457 (12) | 0.0588 (14) | 0.0069 (9) | −0.0049 (10) | −0.0095 (10) |
C15B | 0.0337 (11) | 0.0296 (10) | 0.0483 (12) | 0.0015 (8) | −0.0002 (9) | −0.0057 (8) |
C16B | 0.0232 (9) | 0.0243 (9) | 0.0388 (10) | 0.0016 (7) | 0.0019 (8) | −0.0011 (7) |
C17B | 0.0366 (11) | 0.0483 (11) | 0.0393 (11) | 0.0126 (9) | 0.0079 (9) | 0.0078 (9) |
C18B | 0.0301 (11) | 0.0405 (11) | 0.0498 (13) | 0.0114 (8) | 0.0005 (9) | 0.0021 (9) |
C19B | 0.0269 (10) | 0.0242 (9) | 0.0426 (11) | −0.0016 (7) | −0.0011 (8) | 0.0016 (8) |
C20B | 0.0376 (12) | 0.0339 (10) | 0.0459 (12) | −0.0034 (8) | −0.0051 (9) | 0.0090 (9) |
C21B | 0.0511 (13) | 0.0496 (12) | 0.0419 (12) | −0.0146 (10) | 0.0031 (10) | 0.0101 (10) |
C22B | 0.0441 (13) | 0.0546 (13) | 0.0486 (13) | −0.0076 (10) | 0.0171 (10) | 0.0030 (10) |
C23B | 0.0303 (10) | 0.0367 (10) | 0.0471 (12) | −0.0005 (8) | 0.0087 (9) | 0.0007 (9) |
C24B | 0.0256 (9) | 0.0219 (8) | 0.0385 (10) | −0.0046 (7) | 0.0031 (8) | −0.0008 (7) |
Geometric parameters (Å, º) top
N1A—C3A | 1.328 (2) | N1B—C3B | 1.330 (2) |
N1A—C2A | 1.335 (2) | N1B—C2B | 1.330 (2) |
N2A—C6A | 1.3398 (19) | N2B—C10B | 1.3406 (19) |
N2A—C10A | 1.3419 (19) | N2B—C6B | 1.3439 (19) |
N3A—C14A | 1.332 (2) | N3B—C14B | 1.333 (2) |
N3A—C13A | 1.331 (2) | N3B—C13B | 1.332 (2) |
N4A—C18A | 1.309 (2) | N4B—C18B | 1.313 (2) |
N4A—C17A | 1.366 (2) | N4B—C17B | 1.366 (2) |
C1A—C2A | 1.378 (2) | C1B—C2B | 1.375 (2) |
C1A—C5A | 1.393 (2) | C1B—C5B | 1.388 (2) |
C1A—H1A | 0.9300 | C1B—H1B | 0.9300 |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.386 (2) | C3B—C4B | 1.385 (2) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.387 (2) | C4B—C5B | 1.387 (2) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.489 (2) | C5B—C6B | 1.488 (2) |
C6A—C7A | 1.391 (2) | C6B—C7B | 1.396 (2) |
C7A—C8A | 1.388 (2) | C7B—C8B | 1.385 (2) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.386 (2) | C8B—C9B | 1.385 (2) |
C8A—C16A | 1.493 (2) | C8B—C16B | 1.496 (2) |
C9A—C10A | 1.390 (2) | C9B—C10B | 1.390 (2) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.489 (2) | C10B—C11B | 1.487 (2) |
C11A—C12A | 1.386 (2) | C11B—C15B | 1.383 (2) |
C11A—C15A | 1.385 (2) | C11B—C12B | 1.383 (2) |
C12A—C13A | 1.375 (2) | C12B—C13B | 1.376 (2) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.372 (2) | C14B—C15B | 1.375 (2) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.364 (2) | C16B—C17B | 1.365 (2) |
C16A—C24A | 1.421 (2) | C16B—C24B | 1.421 (2) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—C19A | 1.416 (2) | C18B—C19B | 1.409 (2) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—C20A | 1.415 (2) | C19B—C20B | 1.413 (2) |
C19A—C24A | 1.415 (2) | C19B—C24B | 1.415 (2) |
C20A—C21A | 1.361 (2) | C20B—C21B | 1.356 (3) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.408 (3) | C21B—C22B | 1.405 (3) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.365 (2) | C22B—C23B | 1.360 (3) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.409 (2) | C23B—C24B | 1.412 (2) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
| | | |
C3A—N1A—C2A | 115.63 (15) | C3B—N1B—C2B | 115.29 (15) |
C6A—N2A—C10A | 118.47 (13) | C10B—N2B—C6B | 118.70 (13) |
C14A—N3A—C13A | 115.13 (15) | C14B—N3B—C13B | 115.04 (16) |
C18A—N4A—C17A | 116.68 (15) | C18B—N4B—C17B | 116.52 (16) |
C2A—C1A—C5A | 119.49 (17) | C2B—C1B—C5B | 119.66 (16) |
C2A—C1A—H1A | 120.3 | C2B—C1B—H1B | 120.2 |
C5A—C1A—H1A | 120.3 | C5B—C1B—H1B | 120.2 |
N1A—C2A—C1A | 124.30 (18) | N1B—C2B—C1B | 124.64 (17) |
N1A—C2A—H2A | 117.9 | N1B—C2B—H2B | 117.7 |
C1A—C2A—H2A | 117.9 | C1B—C2B—H2B | 117.7 |
N1A—C3A—C4A | 124.74 (17) | N1B—C3B—C4B | 124.71 (17) |
N1A—C3A—H3A | 117.6 | N1B—C3B—H3B | 117.6 |
C4A—C3A—H3A | 117.6 | C4B—C3B—H3B | 117.6 |
C5A—C4A—C3A | 119.04 (17) | C5B—C4B—C3B | 119.12 (16) |
C5A—C4A—H4A | 120.5 | C5B—C4B—H4B | 120.4 |
C3A—C4A—H4A | 120.5 | C3B—C4B—H4B | 120.4 |
C4A—C5A—C1A | 116.73 (15) | C4B—C5B—C1B | 116.51 (15) |
C4A—C5A—C6A | 123.11 (15) | C4B—C5B—C6B | 123.40 (15) |
C1A—C5A—C6A | 120.16 (15) | C1B—C5B—C6B | 120.09 (14) |
N2A—C6A—C7A | 122.47 (14) | N2B—C6B—C7B | 122.12 (14) |
N2A—C6A—C5A | 115.09 (14) | N2B—C6B—C5B | 114.96 (13) |
C7A—C6A—C5A | 122.37 (14) | C7B—C6B—C5B | 122.91 (14) |
C6A—C7A—C8A | 119.24 (15) | C8B—C7B—C6B | 119.08 (15) |
C6A—C7A—H7A | 120.4 | C8B—C7B—H7B | 120.5 |
C8A—C7A—H7A | 120.4 | C6B—C7B—H7B | 120.5 |
C9A—C8A—C7A | 118.09 (15) | C9B—C8B—C7B | 118.54 (15) |
C9A—C8A—C16A | 119.49 (14) | C9B—C8B—C16B | 118.70 (14) |
C7A—C8A—C16A | 122.40 (15) | C7B—C8B—C16B | 122.72 (15) |
C8A—C9A—C10A | 119.57 (14) | C8B—C9B—C10B | 119.43 (14) |
C8A—C9A—H9A | 120.2 | C8B—C9B—H9B | 120.3 |
C10A—C9A—H9A | 120.2 | C10B—C9B—H9B | 120.3 |
N2A—C10A—C9A | 122.16 (15) | N2B—C10B—C9B | 122.12 (15) |
N2A—C10A—C11A | 116.16 (14) | N2B—C10B—C11B | 116.16 (14) |
C9A—C10A—C11A | 121.68 (14) | C9B—C10B—C11B | 121.64 (14) |
C12A—C11A—C15A | 116.33 (15) | C15B—C11B—C12B | 116.28 (15) |
C12A—C11A—C10A | 121.73 (15) | C15B—C11B—C10B | 121.35 (15) |
C15A—C11A—C10A | 121.94 (14) | C12B—C11B—C10B | 122.33 (14) |
C13A—C12A—C11A | 119.75 (16) | C13B—C12B—C11B | 120.02 (16) |
C13A—C12A—H12A | 120.1 | C13B—C12B—H12B | 120.0 |
C11A—C12A—H12A | 120.1 | C11B—C12B—H12B | 120.0 |
N3A—C13A—C12A | 124.44 (16) | N3B—C13B—C12B | 124.28 (17) |
N3A—C13A—H13A | 117.8 | N3B—C13B—H13B | 117.9 |
C12A—C13A—H13A | 117.8 | C12B—C13B—H13B | 117.9 |
N3A—C14A—C15A | 124.86 (16) | N3B—C14B—C15B | 124.92 (17) |
N3A—C14A—H14A | 117.6 | N3B—C14B—H14B | 117.5 |
C15A—C14A—H14A | 117.6 | C15B—C14B—H14B | 117.5 |
C14A—C15A—C11A | 119.47 (15) | C14B—C15B—C11B | 119.44 (16) |
C14A—C15A—H15A | 120.3 | C14B—C15B—H15B | 120.3 |
C11A—C15A—H15A | 120.3 | C11B—C15B—H15B | 120.3 |
C17A—C16A—C24A | 118.35 (15) | C17B—C16B—C24B | 118.66 (15) |
C17A—C16A—C8A | 120.34 (16) | C17B—C16B—C8B | 120.74 (16) |
C24A—C16A—C8A | 121.29 (14) | C24B—C16B—C8B | 120.54 (15) |
N4A—C17A—C16A | 124.92 (17) | N4B—C17B—C16B | 124.61 (17) |
N4A—C17A—H17A | 117.5 | N4B—C17B—H17B | 117.7 |
C16A—C17A—H17A | 117.5 | C16B—C17B—H17B | 117.7 |
N4A—C18A—C19A | 124.50 (16) | N4B—C18B—C19B | 124.86 (17) |
N4A—C18A—H18A | 117.8 | N4B—C18B—H18B | 117.6 |
C19A—C18A—H18A | 117.8 | C19B—C18B—H18B | 117.6 |
C20A—C19A—C24A | 119.84 (16) | C20B—C19B—C24B | 119.55 (17) |
C20A—C19A—C18A | 122.30 (16) | C20B—C19B—C18B | 122.65 (17) |
C24A—C19A—C18A | 117.86 (16) | C24B—C19B—C18B | 117.80 (16) |
C21A—C20A—C19A | 120.14 (17) | C21B—C20B—C19B | 120.58 (18) |
C21A—C20A—H20A | 119.9 | C21B—C20B—H20B | 119.7 |
C19A—C20A—H20A | 119.9 | C19B—C20B—H20B | 119.7 |
C20A—C21A—C22A | 120.18 (18) | C20B—C21B—C22B | 119.94 (19) |
C20A—C21A—H21A | 119.9 | C20B—C21B—H21B | 120.0 |
C22A—C21A—H21A | 119.9 | C22B—C21B—H21B | 120.0 |
C23A—C22A—C21A | 120.75 (17) | C23B—C22B—C21B | 121.05 (19) |
C23A—C22A—H22A | 119.6 | C23B—C22B—H22B | 119.5 |
C21A—C22A—H22A | 119.6 | C21B—C22B—H22B | 119.5 |
C22A—C23A—C24A | 120.62 (17) | C22B—C23B—C24B | 120.45 (18) |
C22A—C23A—H23A | 119.7 | C22B—C23B—H23B | 119.8 |
C24A—C23A—H23A | 119.7 | C24B—C23B—H23B | 119.8 |
C19A—C24A—C23A | 118.44 (16) | C19B—C24B—C23B | 118.42 (16) |
C19A—C24A—C16A | 117.62 (15) | C19B—C24B—C16B | 117.51 (15) |
C23A—C24A—C16A | 123.93 (15) | C23B—C24B—C16B | 124.06 (16) |
| | | |
C3A—N1A—C2A—C1A | −2.7 (3) | C3B—N1B—C2B—C1B | 2.4 (3) |
C5A—C1A—C2A—N1A | 1.4 (3) | C5B—C1B—C2B—N1B | −0.8 (3) |
C2A—N1A—C3A—C4A | 1.5 (3) | C2B—N1B—C3B—C4B | −1.7 (3) |
N1A—C3A—C4A—C5A | 1.0 (3) | N1B—C3B—C4B—C5B | −0.7 (3) |
C3A—C4A—C5A—C1A | −2.3 (2) | C3B—C4B—C5B—C1B | 2.3 (2) |
C3A—C4A—C5A—C6A | 177.84 (15) | C3B—C4B—C5B—C6B | −177.67 (15) |
C2A—C1A—C5A—C4A | 1.2 (2) | C2B—C1B—C5B—C4B | −1.7 (2) |
C2A—C1A—C5A—C6A | −178.91 (15) | C2B—C1B—C5B—C6B | 178.32 (16) |
C10A—N2A—C6A—C7A | 0.1 (2) | C10B—N2B—C6B—C7B | −1.1 (2) |
C10A—N2A—C6A—C5A | −177.04 (13) | C10B—N2B—C6B—C5B | 178.08 (13) |
C4A—C5A—C6A—N2A | −158.43 (15) | C4B—C5B—C6B—N2B | 170.20 (15) |
C1A—C5A—C6A—N2A | 21.7 (2) | C1B—C5B—C6B—N2B | −9.8 (2) |
C4A—C5A—C6A—C7A | 24.4 (2) | C4B—C5B—C6B—C7B | −10.6 (2) |
C1A—C5A—C6A—C7A | −155.50 (16) | C1B—C5B—C6B—C7B | 169.41 (16) |
N2A—C6A—C7A—C8A | −0.2 (2) | N2B—C6B—C7B—C8B | 1.0 (2) |
C5A—C6A—C7A—C8A | 176.80 (14) | C5B—C6B—C7B—C8B | −178.12 (14) |
C6A—C7A—C8A—C9A | 0.4 (2) | C6B—C7B—C8B—C9B | −0.1 (2) |
C6A—C7A—C8A—C16A | −178.12 (15) | C6B—C7B—C8B—C16B | 177.68 (15) |
C7A—C8A—C9A—C10A | −0.5 (2) | C7B—C8B—C9B—C10B | −0.6 (2) |
C16A—C8A—C9A—C10A | 178.01 (15) | C16B—C8B—C9B—C10B | −178.49 (15) |
C6A—N2A—C10A—C9A | −0.3 (2) | C6B—N2B—C10B—C9B | 0.4 (2) |
C6A—N2A—C10A—C11A | 178.93 (14) | C6B—N2B—C10B—C11B | −176.51 (14) |
C8A—C9A—C10A—N2A | 0.5 (3) | C8B—C9B—C10B—N2B | 0.5 (2) |
C8A—C9A—C10A—C11A | −178.67 (15) | C8B—C9B—C10B—C11B | 177.20 (15) |
N2A—C10A—C11A—C12A | −167.42 (15) | N2B—C10B—C11B—C15B | 10.5 (2) |
C9A—C10A—C11A—C12A | 11.8 (3) | C9B—C10B—C11B—C15B | −166.36 (16) |
N2A—C10A—C11A—C15A | 13.1 (2) | N2B—C10B—C11B—C12B | −171.96 (15) |
C9A—C10A—C11A—C15A | −167.61 (16) | C9B—C10B—C11B—C12B | 11.1 (3) |
C15A—C11A—C12A—C13A | 0.8 (3) | C15B—C11B—C12B—C13B | 1.6 (3) |
C10A—C11A—C12A—C13A | −178.63 (17) | C10B—C11B—C12B—C13B | −175.99 (16) |
C14A—N3A—C13A—C12A | −1.0 (3) | C14B—N3B—C13B—C12B | −0.6 (3) |
C11A—C12A—C13A—N3A | 0.7 (3) | C11B—C12B—C13B—N3B | −0.4 (3) |
C13A—N3A—C14A—C15A | −0.1 (3) | C13B—N3B—C14B—C15B | 0.3 (3) |
N3A—C14A—C15A—C11A | 1.6 (3) | N3B—C14B—C15B—C11B | 1.0 (3) |
C12A—C11A—C15A—C14A | −1.9 (3) | C12B—C11B—C15B—C14B | −1.9 (3) |
C10A—C11A—C15A—C14A | 177.59 (16) | C10B—C11B—C15B—C14B | 175.74 (16) |
C9A—C8A—C16A—C17A | −92.0 (2) | C9B—C8B—C16B—C17B | −89.8 (2) |
C7A—C8A—C16A—C17A | 86.5 (2) | C7B—C8B—C16B—C17B | 92.4 (2) |
C9A—C8A—C16A—C24A | 86.3 (2) | C9B—C8B—C16B—C24B | 87.3 (2) |
C7A—C8A—C16A—C24A | −95.2 (2) | C7B—C8B—C16B—C24B | −90.6 (2) |
C18A—N4A—C17A—C16A | 2.2 (3) | C18B—N4B—C17B—C16B | 1.1 (3) |
C24A—C16A—C17A—N4A | −2.2 (3) | C24B—C16B—C17B—N4B | −1.8 (3) |
C8A—C16A—C17A—N4A | 176.15 (16) | C8B—C16B—C17B—N4B | 175.31 (16) |
C17A—N4A—C18A—C19A | 0.1 (3) | C17B—N4B—C18B—C19B | 0.8 (3) |
N4A—C18A—C19A—C20A | 177.32 (16) | N4B—C18B—C19B—C20B | 177.61 (17) |
N4A—C18A—C19A—C24A | −2.2 (3) | N4B—C18B—C19B—C24B | −2.0 (3) |
C24A—C19A—C20A—C21A | −0.8 (2) | C24B—C19B—C20B—C21B | 0.6 (3) |
C18A—C19A—C20A—C21A | 179.70 (16) | C18B—C19B—C20B—C21B | −178.99 (16) |
C19A—C20A—C21A—C22A | −0.6 (3) | C19B—C20B—C21B—C22B | −1.0 (3) |
C20A—C21A—C22A—C23A | 0.9 (3) | C20B—C21B—C22B—C23B | 0.3 (3) |
C21A—C22A—C23A—C24A | 0.2 (3) | C21B—C22B—C23B—C24B | 0.8 (3) |
C20A—C19A—C24A—C23A | 1.9 (2) | C20B—C19B—C24B—C23B | 0.5 (2) |
C18A—C19A—C24A—C23A | −178.57 (14) | C18B—C19B—C24B—C23B | −179.88 (15) |
C20A—C19A—C24A—C16A | −177.44 (14) | C20B—C19B—C24B—C16B | −178.40 (15) |
C18A—C19A—C24A—C16A | 2.1 (2) | C18B—C19B—C24B—C16B | 1.2 (2) |
C22A—C23A—C24A—C19A | −1.6 (2) | C22B—C23B—C24B—C19B | −1.2 (2) |
C22A—C23A—C24A—C16A | 177.67 (16) | C22B—C23B—C24B—C16B | 177.61 (16) |
C17A—C16A—C24A—C19A | −0.1 (2) | C17B—C16B—C24B—C19B | 0.5 (2) |
C8A—C16A—C24A—C19A | −178.41 (14) | C8B—C16B—C24B—C19B | −176.61 (14) |
C17A—C16A—C24A—C23A | −179.39 (16) | C17B—C16B—C24B—C23B | −178.32 (16) |
C8A—C16A—C24A—C23A | 2.3 (2) | C8B—C16B—C24B—C23B | 4.6 (2) |
Crystal data top
C24H16N4 | F(000) = 1504 |
Mr = 360.41 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 24.2412 (12) Å | Cell parameters from 4418 reflections |
b = 10.4907 (4) Å | θ = 4.1–27.2° |
c = 15.0278 (9) Å | µ = 0.08 mm−1 |
β = 106.656 (5)° | T = 274 K |
V = 3661.3 (3) Å3 | Plate, colourless |
Z = 8 | 0.28 × 0.20 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 7461 independent reflections |
Radiation source: fine-focus sealed tube | 4247 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ω scans, thick slices | θmax = 26.4°, θmin = 3.7° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | h = −30→27 |
| k = −12→13 |
28207 measured reflections | l = −12→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
7461 reflections | Δρmax = 0.39 e Å−3 |
506 parameters | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.18808 (10) | −0.16862 (16) | 0.35055 (17) | 0.0663 (7) | |
N2A | 0.23478 (8) | 0.29578 (14) | 0.36063 (12) | 0.0389 (5) | |
N3A | 0.40198 (9) | 0.59020 (17) | 0.49657 (15) | 0.0612 (7) | |
N4A | 0.00449 (9) | 0.63714 (19) | 0.23205 (16) | 0.0596 (6) | |
C1A | 0.22615 (11) | 0.0390 (2) | 0.3996 (2) | 0.0644 (9) | |
H1A | 0.2542 | 0.0875 | 0.4411 | 0.077* | |
C2A | 0.22606 (12) | −0.0918 (2) | 0.4083 (2) | 0.0766 (10) | |
H2A | 0.2540 | −0.1289 | 0.4572 | 0.092* | |
C3A | 0.14758 (12) | −0.1107 (2) | 0.28487 (18) | 0.0565 (7) | |
H3A | 0.1200 | −0.1615 | 0.2446 | 0.068* | |
C4A | 0.14335 (11) | 0.02014 (18) | 0.27177 (17) | 0.0495 (7) | |
H4A | 0.1133 | 0.0550 | 0.2251 | 0.059* | |
C5A | 0.18446 (10) | 0.09806 (18) | 0.32909 (16) | 0.0429 (6) | |
C6A | 0.18458 (9) | 0.23953 (17) | 0.31861 (15) | 0.0378 (6) | |
C7A | 0.13559 (9) | 0.30723 (18) | 0.27145 (15) | 0.0400 (6) | |
H7A | 0.1014 | 0.2649 | 0.2429 | 0.048* | |
C8A | 0.13878 (9) | 0.43928 (18) | 0.26791 (15) | 0.0386 (5) | |
C9A | 0.19090 (10) | 0.49708 (18) | 0.31163 (16) | 0.0423 (6) | |
H9A | 0.1943 | 0.5853 | 0.3103 | 0.051* | |
C10A | 0.23795 (9) | 0.42314 (18) | 0.35745 (14) | 0.0374 (5) | |
C11A | 0.29454 (9) | 0.48063 (17) | 0.40668 (15) | 0.0386 (6) | |
C12A | 0.30092 (10) | 0.60995 (19) | 0.42239 (18) | 0.0545 (7) | |
H12A | 0.2692 | 0.6638 | 0.4032 | 0.065* | |
C13A | 0.35438 (11) | 0.6590 (2) | 0.46657 (19) | 0.0617 (8) | |
H13A | 0.3573 | 0.7466 | 0.4761 | 0.074* | |
C14A | 0.39511 (11) | 0.4658 (2) | 0.48188 (19) | 0.0626 (8) | |
H14A | 0.4275 | 0.4141 | 0.5020 | 0.075* | |
C15A | 0.34361 (10) | 0.40810 (19) | 0.43916 (16) | 0.0509 (7) | |
H15A | 0.3418 | 0.3200 | 0.4321 | 0.061* | |
C16A | 0.08792 (9) | 0.51947 (18) | 0.22076 (16) | 0.0387 (6) | |
C17A | 0.05031 (11) | 0.5577 (2) | 0.26674 (17) | 0.0529 (7) | |
H17A | 0.0561 | 0.5274 | 0.3269 | 0.063* | |
C18A | −0.00383 (10) | 0.6753 (2) | 0.14601 (19) | 0.0522 (7) | |
H18A | −0.0348 | 0.7293 | 0.1210 | 0.063* | |
C19A | 0.03058 (9) | 0.64051 (18) | 0.08884 (16) | 0.0403 (6) | |
C20A | 0.01854 (11) | 0.6802 (2) | −0.00466 (18) | 0.0516 (7) | |
H20A | −0.0133 | 0.7313 | −0.0307 | 0.062* | |
C21A | 0.05315 (12) | 0.6440 (2) | −0.05632 (18) | 0.0592 (7) | |
H21A | 0.0448 | 0.6697 | −0.1180 | 0.071* | |
C22A | 0.10160 (12) | 0.5680 (2) | −0.01725 (18) | 0.0598 (7) | |
H22A | 0.1255 | 0.5449 | −0.0532 | 0.072* | |
C23A | 0.11426 (11) | 0.5274 (2) | 0.07208 (17) | 0.0495 (6) | |
H23A | 0.1465 | 0.4767 | 0.0966 | 0.059* | |
C24A | 0.07887 (9) | 0.56164 (17) | 0.12769 (15) | 0.0376 (6) | |
N1B | 0.68040 (10) | −0.16919 (16) | 0.29711 (16) | 0.0637 (7) | |
N2B | 0.71906 (7) | 0.29631 (14) | 0.35167 (12) | 0.0374 (5) | |
N3B | 0.88577 (9) | 0.58733 (18) | 0.49639 (15) | 0.0601 (6) | |
N4B | 0.48872 (9) | 0.64172 (19) | 0.22822 (15) | 0.0613 (6) | |
C1B | 0.72426 (11) | 0.03664 (19) | 0.33241 (19) | 0.0603 (8) | |
H1B | 0.7580 | 0.0829 | 0.3567 | 0.072* | |
C2B | 0.72577 (12) | −0.0948 (2) | 0.3292 (2) | 0.0720 (9) | |
H2B | 0.7615 | −0.1341 | 0.3512 | 0.086* | |
C3B | 0.63135 (11) | −0.1081 (2) | 0.26244 (17) | 0.0542 (7) | |
H3B | 0.5986 | −0.1569 | 0.2370 | 0.065* | |
C4B | 0.62491 (10) | 0.02313 (18) | 0.26106 (16) | 0.0457 (6) | |
H4B | 0.5890 | 0.0598 | 0.2346 | 0.055* | |
C5B | 0.67210 (10) | 0.09872 (17) | 0.29914 (15) | 0.0391 (6) | |
C6B | 0.66977 (9) | 0.24057 (17) | 0.30338 (14) | 0.0354 (5) | |
C7B | 0.62073 (9) | 0.31019 (17) | 0.25995 (15) | 0.0390 (6) | |
H7B | 0.5870 | 0.2688 | 0.2278 | 0.047* | |
C8B | 0.62261 (9) | 0.44194 (17) | 0.26501 (15) | 0.0371 (5) | |
C9B | 0.67357 (9) | 0.49909 (18) | 0.31427 (15) | 0.0403 (6) | |
H9B | 0.6762 | 0.5874 | 0.3188 | 0.048* | |
C10B | 0.72095 (9) | 0.42373 (17) | 0.35699 (14) | 0.0363 (5) | |
C11B | 0.77745 (9) | 0.48010 (17) | 0.40768 (15) | 0.0379 (5) | |
C12B | 0.78433 (10) | 0.60836 (19) | 0.42797 (17) | 0.0521 (7) | |
H12B | 0.7526 | 0.6624 | 0.4123 | 0.062* | |
C13B | 0.83822 (11) | 0.6564 (2) | 0.47151 (18) | 0.0569 (7) | |
H13B | 0.8413 | 0.7433 | 0.4843 | 0.068* | |
C14B | 0.87848 (11) | 0.4640 (2) | 0.47781 (19) | 0.0649 (8) | |
H14B | 0.9109 | 0.4121 | 0.4948 | 0.078* | |
C15B | 0.82665 (10) | 0.4070 (2) | 0.43542 (17) | 0.0524 (7) | |
H15B | 0.8247 | 0.3195 | 0.4254 | 0.063* | |
C16B | 0.57231 (9) | 0.52409 (17) | 0.21792 (16) | 0.0373 (6) | |
C17B | 0.53368 (11) | 0.5598 (2) | 0.26318 (17) | 0.0529 (7) | |
H17B | 0.5381 | 0.5263 | 0.3221 | 0.063* | |
C18B | 0.48297 (11) | 0.6853 (2) | 0.14392 (19) | 0.0548 (7) | |
H18B | 0.4529 | 0.7417 | 0.1191 | 0.066* | |
C19B | 0.51874 (9) | 0.65343 (18) | 0.08870 (17) | 0.0417 (6) | |
C20B | 0.50934 (12) | 0.7001 (2) | −0.00304 (19) | 0.0574 (8) | |
H20B | 0.4787 | 0.7549 | −0.0283 | 0.069* | |
C21B | 0.54445 (13) | 0.6656 (2) | −0.05344 (19) | 0.0646 (8) | |
H21B | 0.5378 | 0.6959 | −0.1138 | 0.078* | |
C22B | 0.59118 (12) | 0.5840 (2) | −0.01563 (19) | 0.0627 (7) | |
H22B | 0.6152 | 0.5606 | −0.0512 | 0.075* | |
C23B | 0.60167 (10) | 0.5390 (2) | 0.07253 (18) | 0.0500 (6) | |
H23B | 0.6332 | 0.4864 | 0.0970 | 0.060* | |
C24B | 0.56555 (9) | 0.57097 (17) | 0.12680 (15) | 0.0373 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0658 (16) | 0.0290 (10) | 0.1009 (19) | 0.0011 (11) | 0.0187 (14) | −0.0021 (11) |
N2A | 0.0398 (12) | 0.0271 (9) | 0.0482 (12) | 0.0016 (8) | 0.0098 (9) | −0.0017 (8) |
N3A | 0.0464 (14) | 0.0445 (11) | 0.0795 (16) | −0.0037 (10) | −0.0031 (11) | −0.0039 (11) |
N4A | 0.0459 (14) | 0.0684 (13) | 0.0625 (15) | 0.0180 (11) | 0.0123 (11) | 0.0010 (11) |
C1A | 0.0469 (16) | 0.0337 (13) | 0.100 (2) | 0.0034 (11) | 0.0004 (15) | 0.0005 (13) |
C2A | 0.0573 (19) | 0.0372 (14) | 0.122 (3) | 0.0071 (13) | 0.0037 (18) | 0.0043 (15) |
C3A | 0.0674 (19) | 0.0369 (13) | 0.0662 (18) | −0.0118 (12) | 0.0204 (15) | −0.0093 (12) |
C4A | 0.0577 (17) | 0.0305 (11) | 0.0585 (16) | −0.0021 (11) | 0.0137 (13) | −0.0002 (11) |
C5A | 0.0428 (14) | 0.0282 (11) | 0.0593 (15) | −0.0024 (10) | 0.0171 (12) | −0.0024 (10) |
C6A | 0.0399 (14) | 0.0265 (10) | 0.0466 (14) | −0.0002 (9) | 0.0120 (11) | −0.0017 (9) |
C7A | 0.0378 (14) | 0.0331 (11) | 0.0463 (14) | −0.0027 (10) | 0.0075 (11) | −0.0027 (10) |
C8A | 0.0402 (14) | 0.0324 (11) | 0.0420 (13) | 0.0031 (10) | 0.0096 (10) | 0.0017 (10) |
C9A | 0.0440 (15) | 0.0254 (10) | 0.0532 (15) | 0.0007 (9) | 0.0070 (11) | 0.0052 (10) |
C10A | 0.0388 (14) | 0.0275 (10) | 0.0441 (13) | 0.0017 (9) | 0.0092 (10) | 0.0011 (9) |
C11A | 0.0402 (14) | 0.0295 (11) | 0.0427 (14) | 0.0000 (9) | 0.0064 (11) | 0.0010 (9) |
C12A | 0.0436 (15) | 0.0286 (11) | 0.0802 (19) | 0.0015 (10) | 0.0000 (13) | 0.0014 (11) |
C13A | 0.0509 (17) | 0.0315 (12) | 0.092 (2) | −0.0033 (11) | 0.0025 (15) | −0.0034 (12) |
C14A | 0.0461 (16) | 0.0406 (13) | 0.086 (2) | 0.0070 (11) | −0.0059 (14) | −0.0032 (13) |
C15A | 0.0505 (16) | 0.0309 (11) | 0.0602 (16) | 0.0031 (10) | −0.0020 (13) | 0.0017 (11) |
C16A | 0.0340 (13) | 0.0294 (11) | 0.0496 (14) | −0.0004 (9) | 0.0067 (11) | −0.0004 (10) |
C17A | 0.0451 (16) | 0.0587 (15) | 0.0527 (16) | 0.0111 (12) | 0.0106 (13) | 0.0079 (12) |
C18A | 0.0367 (15) | 0.0469 (13) | 0.0651 (18) | 0.0105 (11) | 0.0019 (13) | 0.0012 (13) |
C19A | 0.0350 (13) | 0.0304 (11) | 0.0503 (15) | −0.0016 (9) | 0.0038 (11) | 0.0006 (10) |
C20A | 0.0442 (16) | 0.0396 (12) | 0.0605 (17) | −0.0043 (11) | −0.0020 (13) | 0.0053 (12) |
C21A | 0.066 (2) | 0.0561 (15) | 0.0487 (16) | −0.0100 (14) | 0.0049 (14) | 0.0062 (12) |
C22A | 0.066 (2) | 0.0587 (15) | 0.0575 (18) | −0.0013 (14) | 0.0216 (14) | −0.0009 (13) |
C23A | 0.0482 (16) | 0.0430 (12) | 0.0539 (16) | 0.0040 (11) | 0.0094 (13) | 0.0018 (12) |
C24A | 0.0373 (13) | 0.0248 (10) | 0.0468 (14) | −0.0036 (9) | 0.0056 (11) | −0.0025 (9) |
N1B | 0.0627 (16) | 0.0317 (10) | 0.0937 (18) | 0.0009 (10) | 0.0174 (13) | 0.0031 (11) |
N2B | 0.0348 (11) | 0.0274 (9) | 0.0459 (11) | 0.0017 (8) | 0.0051 (9) | 0.0035 (8) |
N3B | 0.0427 (13) | 0.0544 (12) | 0.0710 (15) | −0.0059 (10) | −0.0030 (11) | −0.0083 (11) |
N4B | 0.0458 (14) | 0.0716 (13) | 0.0626 (15) | 0.0235 (11) | 0.0095 (11) | 0.0021 (11) |
C1B | 0.0490 (16) | 0.0326 (12) | 0.090 (2) | 0.0034 (11) | 0.0056 (15) | 0.0058 (12) |
C2B | 0.0579 (19) | 0.0390 (14) | 0.110 (3) | 0.0068 (13) | 0.0088 (17) | 0.0105 (14) |
C3B | 0.0593 (18) | 0.0356 (12) | 0.0682 (18) | −0.0116 (12) | 0.0192 (14) | −0.0080 (12) |
C4B | 0.0439 (14) | 0.0342 (11) | 0.0557 (15) | −0.0002 (10) | 0.0092 (12) | −0.0037 (10) |
C5B | 0.0416 (14) | 0.0264 (10) | 0.0476 (14) | −0.0002 (9) | 0.0103 (11) | 0.0032 (9) |
C6B | 0.0369 (13) | 0.0258 (10) | 0.0422 (13) | 0.0008 (9) | 0.0092 (10) | 0.0023 (9) |
C7B | 0.0351 (13) | 0.0309 (11) | 0.0465 (14) | −0.0028 (9) | 0.0041 (10) | −0.0001 (9) |
C8B | 0.0344 (13) | 0.0318 (11) | 0.0428 (13) | 0.0025 (9) | 0.0073 (10) | 0.0043 (9) |
C9B | 0.0366 (13) | 0.0242 (10) | 0.0557 (15) | 0.0024 (9) | 0.0060 (11) | 0.0021 (9) |
C10B | 0.0366 (13) | 0.0252 (10) | 0.0443 (13) | 0.0013 (9) | 0.0073 (10) | 0.0036 (9) |
C11B | 0.0379 (13) | 0.0311 (11) | 0.0405 (13) | 0.0012 (9) | 0.0044 (10) | 0.0035 (9) |
C12B | 0.0419 (15) | 0.0308 (12) | 0.0716 (18) | 0.0015 (10) | −0.0029 (13) | 0.0048 (11) |
C13B | 0.0543 (17) | 0.0363 (12) | 0.0677 (18) | −0.0088 (12) | −0.0023 (14) | −0.0005 (12) |
C14B | 0.0426 (16) | 0.0547 (15) | 0.080 (2) | 0.0074 (12) | −0.0100 (14) | −0.0132 (13) |
C15B | 0.0447 (15) | 0.0350 (12) | 0.0664 (17) | 0.0051 (11) | −0.0019 (13) | −0.0071 (11) |
C16B | 0.0330 (13) | 0.0277 (10) | 0.0475 (14) | 0.0021 (9) | 0.0055 (11) | −0.0007 (10) |
C17B | 0.0463 (16) | 0.0578 (15) | 0.0507 (15) | 0.0139 (12) | 0.0077 (12) | 0.0063 (12) |
C18B | 0.0382 (15) | 0.0485 (14) | 0.0668 (19) | 0.0137 (11) | −0.0024 (13) | 0.0012 (13) |
C19B | 0.0336 (13) | 0.0302 (11) | 0.0532 (15) | −0.0009 (9) | −0.0007 (11) | 0.0009 (10) |
C20B | 0.0511 (18) | 0.0436 (14) | 0.0628 (18) | −0.0037 (12) | −0.0069 (14) | 0.0107 (12) |
C21B | 0.072 (2) | 0.0595 (16) | 0.0552 (18) | −0.0173 (15) | 0.0063 (16) | 0.0140 (14) |
C22B | 0.0610 (19) | 0.0708 (17) | 0.0585 (18) | −0.0070 (15) | 0.0207 (14) | 0.0037 (14) |
C23B | 0.0408 (15) | 0.0486 (13) | 0.0586 (17) | −0.0009 (11) | 0.0108 (13) | 0.0035 (12) |
C24B | 0.0321 (13) | 0.0266 (10) | 0.0485 (14) | −0.0035 (9) | 0.0041 (11) | −0.0006 (10) |
Geometric parameters (Å, º) top
N1A—C3A | 1.323 (3) | N1B—C3B | 1.319 (3) |
N1A—C2A | 1.339 (3) | N1B—C2B | 1.322 (3) |
N2A—C10A | 1.340 (2) | N2B—C10B | 1.339 (2) |
N2A—C6A | 1.337 (2) | N2B—C6B | 1.341 (2) |
N3A—C14A | 1.327 (3) | N3B—C14B | 1.325 (3) |
N3A—C13A | 1.326 (3) | N3B—C13B | 1.321 (3) |
N4A—C18A | 1.313 (3) | N4B—C18B | 1.316 (3) |
N4A—C17A | 1.367 (3) | N4B—C17B | 1.369 (3) |
C1A—C2A | 1.379 (3) | C1B—C2B | 1.381 (3) |
C1A—C5A | 1.384 (3) | C1B—C5B | 1.382 (3) |
C1A—H1A | 0.9300 | C1B—H1B | 0.9300 |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.387 (3) | C3B—C4B | 1.385 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.382 (3) | C4B—C5B | 1.375 (3) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.493 (2) | C5B—C6B | 1.491 (2) |
C6A—C7A | 1.391 (3) | C6B—C7B | 1.389 (3) |
C7A—C8A | 1.389 (2) | C7B—C8B | 1.384 (2) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.386 (3) | C8B—C9B | 1.382 (3) |
C8A—C16A | 1.493 (3) | C8B—C16B | 1.495 (3) |
C9A—C10A | 1.388 (3) | C9B—C10B | 1.391 (3) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.487 (3) | C10B—C11B | 1.486 (3) |
C11A—C12A | 1.378 (3) | C11B—C12B | 1.379 (3) |
C11A—C15A | 1.378 (3) | C11B—C15B | 1.378 (3) |
C12A—C13A | 1.376 (3) | C12B—C13B | 1.378 (3) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.370 (3) | C14B—C15B | 1.372 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.353 (3) | C16B—C17B | 1.358 (3) |
C16A—C24A | 1.423 (3) | C16B—C24B | 1.420 (3) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—C19A | 1.406 (3) | C18B—C19B | 1.402 (3) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—C20A | 1.413 (3) | C19B—C20B | 1.418 (3) |
C19A—C24A | 1.415 (3) | C19B—C24B | 1.411 (3) |
C20A—C21A | 1.350 (4) | C20B—C21B | 1.341 (4) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.402 (3) | C21B—C22B | 1.403 (4) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.357 (3) | C22B—C23B | 1.360 (3) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.405 (3) | C23B—C24B | 1.398 (3) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
| | | |
C3A—N1A—C2A | 115.66 (19) | C3B—N1B—C2B | 114.76 (19) |
C10A—N2A—C6A | 118.50 (17) | C10B—N2B—C6B | 118.52 (16) |
C14A—N3A—C13A | 115.1 (2) | C14B—N3B—C13B | 115.0 (2) |
C18A—N4A—C17A | 116.1 (2) | C18B—N4B—C17B | 116.1 (2) |
C2A—C1A—C5A | 119.8 (2) | C2B—C1B—C5B | 119.2 (2) |
C2A—C1A—H1A | 120.1 | C2B—C1B—H1B | 120.4 |
C5A—C1A—H1A | 120.1 | C5B—C1B—H1B | 120.4 |
N1A—C2A—C1A | 123.8 (2) | N1B—C2B—C1B | 125.1 (2) |
N1A—C2A—H2A | 118.1 | N1B—C2B—H2B | 117.5 |
C1A—C2A—H2A | 118.1 | C1B—C2B—H2B | 117.5 |
N1A—C3A—C4A | 124.7 (2) | N1B—C3B—C4B | 125.0 (2) |
N1A—C3A—H3A | 117.7 | N1B—C3B—H3B | 117.5 |
C4A—C3A—H3A | 117.7 | C4B—C3B—H3B | 117.5 |
C5A—C4A—C3A | 119.1 (2) | C3B—C4B—C5B | 119.4 (2) |
C5A—C4A—H4A | 120.5 | C3B—C4B—H4B | 120.3 |
C3A—C4A—H4A | 120.5 | C5B—C4B—H4B | 120.3 |
C4A—C5A—C1A | 116.78 (18) | C4B—C5B—C1B | 116.40 (18) |
C4A—C5A—C6A | 123.04 (19) | C4B—C5B—C6B | 123.80 (19) |
C1A—C5A—C6A | 120.17 (19) | C1B—C5B—C6B | 119.77 (19) |
N2A—C6A—C7A | 122.95 (17) | N2B—C6B—C7B | 122.34 (16) |
N2A—C6A—C5A | 114.73 (17) | N2B—C6B—C5B | 114.80 (17) |
C7A—C6A—C5A | 122.29 (18) | C7B—C6B—C5B | 122.86 (18) |
C8A—C7A—C6A | 118.68 (19) | C8B—C7B—C6B | 119.28 (18) |
C8A—C7A—H7A | 120.7 | C8B—C7B—H7B | 120.4 |
C6A—C7A—H7A | 120.7 | C6B—C7B—H7B | 120.4 |
C9A—C8A—C7A | 118.12 (18) | C9B—C8B—C7B | 118.23 (18) |
C9A—C8A—C16A | 119.68 (17) | C9B—C8B—C16B | 119.08 (16) |
C7A—C8A—C16A | 122.18 (19) | C7B—C8B—C16B | 122.68 (18) |
C8A—C9A—C10A | 119.91 (17) | C8B—C9B—C10B | 119.60 (17) |
C8A—C9A—H9A | 120.0 | C8B—C9B—H9B | 120.2 |
C10A—C9A—H9A | 120.0 | C10B—C9B—H9B | 120.2 |
N2A—C10A—C9A | 121.84 (18) | N2B—C10B—C9B | 122.03 (18) |
N2A—C10A—C11A | 116.16 (17) | N2B—C10B—C11B | 116.01 (17) |
C9A—C10A—C11A | 122.00 (17) | C9B—C10B—C11B | 121.90 (16) |
C12A—C11A—C15A | 116.10 (19) | C12B—C11B—C15B | 115.88 (19) |
C12A—C11A—C10A | 121.78 (19) | C12B—C11B—C10B | 122.47 (18) |
C15A—C11A—C10A | 122.13 (17) | C15B—C11B—C10B | 121.63 (17) |
C13A—C12A—C11A | 119.7 (2) | C13B—C12B—C11B | 120.0 (2) |
C13A—C12A—H12A | 120.2 | C13B—C12B—H12B | 120.0 |
C11A—C12A—H12A | 120.2 | C11B—C12B—H12B | 120.0 |
N3A—C13A—C12A | 124.6 (2) | N3B—C13B—C12B | 124.4 (2) |
N3A—C13A—H13A | 117.7 | N3B—C13B—H13B | 117.8 |
C12A—C13A—H13A | 117.7 | C12B—C13B—H13B | 117.8 |
N3A—C14A—C15A | 124.5 (2) | N3B—C14B—C15B | 124.9 (2) |
N3A—C14A—H14A | 117.7 | N3B—C14B—H14B | 117.6 |
C15A—C14A—H14A | 117.7 | C15B—C14B—H14B | 117.6 |
C14A—C15A—C11A | 120.02 (19) | C14B—C15B—C11B | 119.77 (19) |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 120.1 |
C11A—C15A—H15A | 120.0 | C11B—C15B—H15B | 120.1 |
C17A—C16A—C24A | 118.3 (2) | C17B—C16B—C24B | 118.8 (2) |
C17A—C16A—C8A | 120.7 (2) | C17B—C16B—C8B | 120.5 (2) |
C24A—C16A—C8A | 121.0 (2) | C24B—C16B—C8B | 120.6 (2) |
N4A—C17A—C16A | 125.4 (2) | N4B—C17B—C16B | 124.6 (2) |
N4A—C17A—H17A | 117.3 | N4B—C17B—H17B | 117.7 |
C16A—C17A—H17A | 117.3 | C16B—C17B—H17B | 117.7 |
N4A—C18A—C19A | 124.9 (2) | N4B—C18B—C19B | 125.0 (2) |
N4A—C18A—H18A | 117.5 | N4B—C18B—H18B | 117.5 |
C19A—C18A—H18A | 117.5 | C19B—C18B—H18B | 117.5 |
C20A—C19A—C24A | 119.5 (2) | C20B—C19B—C24B | 119.5 (2) |
C20A—C19A—C18A | 122.8 (2) | C20B—C19B—C18B | 122.6 (2) |
C24A—C19A—C18A | 117.7 (2) | C24B—C19B—C18B | 117.9 (2) |
C21A—C20A—C19A | 120.2 (2) | C21B—C20B—C19B | 120.3 (2) |
C21A—C20A—H20A | 119.9 | C21B—C20B—H20B | 119.8 |
C19A—C20A—H20A | 119.9 | C19B—C20B—H20B | 119.8 |
C20A—C21A—C22A | 120.2 (2) | C20B—C21B—C22B | 120.3 (3) |
C20A—C21A—H21A | 119.9 | C20B—C21B—H21B | 119.8 |
C22A—C21A—H21A | 119.9 | C22B—C21B—H21B | 119.8 |
C23A—C22A—C21A | 121.2 (3) | C23B—C22B—C21B | 120.7 (3) |
C23A—C22A—H22A | 119.4 | C23B—C22B—H22B | 119.7 |
C21A—C22A—H22A | 119.4 | C21B—C22B—H22B | 119.7 |
C22A—C23A—C24A | 120.3 (2) | C22B—C23B—C24B | 120.8 (2) |
C22A—C23A—H23A | 119.8 | C22B—C23B—H23B | 119.6 |
C24A—C23A—H23A | 119.8 | C24B—C23B—H23B | 119.6 |
C19A—C24A—C16A | 117.6 (2) | C16B—C24B—C19B | 117.4 (2) |
C19A—C24A—C23A | 118.5 (2) | C16B—C24B—C23B | 124.1 (2) |
C16A—C24A—C23A | 123.8 (2) | C19B—C24B—C23B | 118.4 (2) |
| | | |
C3A—N1A—C2A—C1A | −3.1 (5) | C3B—N1B—C2B—C1B | 3.3 (4) |
C5A—C1A—C2A—N1A | 1.5 (5) | C5B—C1B—C2B—N1B | −0.8 (5) |
C2A—N1A—C3A—C4A | 1.6 (4) | C2B—N1B—C3B—C4B | −2.4 (4) |
N1A—C3A—C4A—C5A | 1.4 (4) | N1B—C3B—C4B—C5B | −0.9 (4) |
C3A—C4A—C5A—C1A | −3.0 (4) | C3B—C4B—C5B—C1B | 3.3 (3) |
C3A—C4A—C5A—C6A | 178.1 (2) | C3B—C4B—C5B—C6B | −178.5 (2) |
C2A—C1A—C5A—C4A | 1.7 (4) | C2B—C1B—C5B—C4B | −2.6 (4) |
C2A—C1A—C5A—C6A | −179.4 (2) | C2B—C1B—C5B—C6B | 179.2 (2) |
C10A—N2A—C6A—C7A | 0.3 (3) | C10B—N2B—C6B—C7B | −0.8 (3) |
C10A—N2A—C6A—C5A | −177.61 (19) | C10B—N2B—C6B—C5B | 178.48 (18) |
C4A—C5A—C6A—N2A | −161.8 (2) | C4B—C5B—C6B—N2B | 173.4 (2) |
C1A—C5A—C6A—N2A | 19.4 (3) | C1B—C5B—C6B—N2B | −8.5 (3) |
C4A—C5A—C6A—C7A | 20.3 (4) | C4B—C5B—C6B—C7B | −7.3 (4) |
C1A—C5A—C6A—C7A | −158.5 (2) | C1B—C5B—C6B—C7B | 170.8 (2) |
N2A—C6A—C7A—C8A | −0.2 (3) | N2B—C6B—C7B—C8B | 1.1 (3) |
C5A—C6A—C7A—C8A | 177.5 (2) | C5B—C6B—C7B—C8B | −178.2 (2) |
C6A—C7A—C8A—C9A | 0.1 (3) | C6B—C7B—C8B—C9B | −0.6 (3) |
C6A—C7A—C8A—C16A | −178.5 (2) | C6B—C7B—C8B—C16B | 178.1 (2) |
C7A—C8A—C9A—C10A | −0.2 (3) | C7B—C8B—C9B—C10B | −0.1 (3) |
C16A—C8A—C9A—C10A | 178.5 (2) | C16B—C8B—C9B—C10B | −178.9 (2) |
C6A—N2A—C10A—C9A | −0.3 (3) | C6B—N2B—C10B—C9B | 0.1 (3) |
C6A—N2A—C10A—C11A | 179.0 (2) | C6B—N2B—C10B—C11B | −177.3 (2) |
C8A—C9A—C10A—N2A | 0.3 (4) | C8B—C9B—C10B—N2B | 0.4 (3) |
C8A—C9A—C10A—C11A | −179.0 (2) | C8B—C9B—C10B—C11B | 177.6 (2) |
N2A—C10A—C11A—C12A | −168.6 (2) | N2B—C10B—C11B—C12B | −172.4 (2) |
C9A—C10A—C11A—C12A | 10.7 (4) | C9B—C10B—C11B—C12B | 10.3 (4) |
N2A—C10A—C11A—C15A | 11.4 (3) | N2B—C10B—C11B—C15B | 9.2 (3) |
C9A—C10A—C11A—C15A | −169.2 (2) | C9B—C10B—C11B—C15B | −168.2 (2) |
C15A—C11A—C12A—C13A | 1.3 (4) | C15B—C11B—C12B—C13B | 1.4 (4) |
C10A—C11A—C12A—C13A | −178.7 (2) | C10B—C11B—C12B—C13B | −177.1 (2) |
C14A—N3A—C13A—C12A | −0.6 (4) | C14B—N3B—C13B—C12B | −1.0 (4) |
C11A—C12A—C13A—N3A | −0.1 (5) | C11B—C12B—C13B—N3B | 0.1 (4) |
C13A—N3A—C14A—C15A | 0.1 (4) | C13B—N3B—C14B—C15B | 0.5 (4) |
N3A—C14A—C15A—C11A | 1.1 (4) | N3B—C14B—C15B—C11B | 1.0 (5) |
C12A—C11A—C15A—C14A | −1.7 (4) | C12B—C11B—C15B—C14B | −1.9 (4) |
C10A—C11A—C15A—C14A | 178.2 (2) | C10B—C11B—C15B—C14B | 176.6 (2) |
C9A—C8A—C16A—C17A | −92.5 (3) | C9B—C8B—C16B—C17B | −90.3 (3) |
C7A—C8A—C16A—C17A | 86.1 (3) | C7B—C8B—C16B—C17B | 91.0 (3) |
C9A—C8A—C16A—C24A | 85.2 (3) | C9B—C8B—C16B—C24B | 86.7 (3) |
C7A—C8A—C16A—C24A | −96.2 (3) | C7B—C8B—C16B—C24B | −92.0 (3) |
C18A—N4A—C17A—C16A | 2.1 (4) | C18B—N4B—C17B—C16B | 1.4 (3) |
C24A—C16A—C17A—N4A | −1.8 (3) | C24B—C16B—C17B—N4B | −1.8 (3) |
C8A—C16A—C17A—N4A | 175.9 (2) | C8B—C16B—C17B—N4B | 175.26 (19) |
C17A—N4A—C18A—C19A | −0.1 (3) | C17B—N4B—C18B—C19B | 0.5 (4) |
N4A—C18A—C19A—C20A | 177.5 (2) | N4B—C18B—C19B—C20B | 177.8 (2) |
N4A—C18A—C19A—C24A | −2.0 (3) | N4B—C18B—C19B—C24B | −1.8 (3) |
C24A—C19A—C20A—C21A | −0.6 (3) | C24B—C19B—C20B—C21B | 0.4 (3) |
C18A—C19A—C20A—C21A | 179.9 (2) | C18B—C19B—C20B—C21B | −179.2 (2) |
C19A—C20A—C21A—C22A | −0.6 (4) | C19B—C20B—C21B—C22B | −0.7 (4) |
C20A—C21A—C22A—C23A | 1.1 (4) | C20B—C21B—C22B—C23B | −0.1 (4) |
C21A—C22A—C23A—C24A | −0.3 (3) | C21B—C22B—C23B—C24B | 1.2 (4) |
C20A—C19A—C24A—C16A | −177.33 (18) | C17B—C16B—C24B—C19B | 0.4 (3) |
C18A—C19A—C24A—C16A | 2.2 (3) | C8B—C16B—C24B—C19B | −176.70 (17) |
C20A—C19A—C24A—C23A | 1.4 (3) | C17B—C16B—C24B—C23B | −178.6 (2) |
C18A—C19A—C24A—C23A | −179.09 (19) | C8B—C16B—C24B—C23B | 4.3 (3) |
C17A—C16A—C24A—C19A | −0.4 (3) | C20B—C19B—C24B—C16B | −178.37 (18) |
C8A—C16A—C24A—C19A | −178.15 (17) | C18B—C19B—C24B—C16B | 1.3 (3) |
C17A—C16A—C24A—C23A | −179.1 (2) | C20B—C19B—C24B—C23B | 0.7 (3) |
C8A—C16A—C24A—C23A | 3.2 (3) | C18B—C19B—C24B—C23B | −179.68 (19) |
C22A—C23A—C24A—C19A | −0.9 (3) | C22B—C23B—C24B—C16B | 177.51 (19) |
C22A—C23A—C24A—C16A | 177.69 (19) | C22B—C23B—C24B—C19B | −1.5 (3) |
Crystal data top
C24H16N4 | F(000) = 752 |
Mr = 360.41 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2957 (2) Å | Cell parameters from 2612 reflections |
b = 10.5239 (2) Å | θ = 4.3–26.0° |
c = 14.9250 (3) Å | µ = 0.08 mm−1 |
β = 107.508 (2)° | T = 277 K |
V = 1841.81 (6) Å3 | Plate, colourless |
Z = 4 | 0.28 × 0.20 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 3773 independent reflections |
Radiation source: fine-focus sealed tube | 2653 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans, thick slices | θmax = 26.4°, θmin = 3.8° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | h = −15→15 |
| k = −13→13 |
36886 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 18 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3773 reflections | Δρmax = 0.14 e Å−3 |
272 parameters | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1A | 0.3664 (5) | −0.1673 (4) | 0.3412 (3) | 0.0621 (12) | 0.481 (3) |
C1A | 0.4425 (4) | 0.0389 (3) | 0.3916 (3) | 0.0576 (9) | 0.481 (3) |
H1A | 0.4992 | 0.0867 | 0.4333 | 0.069* | 0.481 (3) |
C2A | 0.4437 (3) | −0.0916 (3) | 0.3978 (3) | 0.0686 (10) | 0.481 (3) |
H2A | 0.5025 | −0.1293 | 0.4447 | 0.082* | 0.481 (3) |
C3A | 0.2842 (5) | −0.1094 (7) | 0.2754 (6) | 0.0566 (5) | 0.481 (3) |
H3A | 0.2290 | −0.1599 | 0.2346 | 0.068* | 0.481 (3) |
C4A | 0.2748 (5) | 0.0215 (7) | 0.2630 (7) | 0.0472 (9) | 0.481 (3) |
H4A | 0.2149 | 0.0566 | 0.2156 | 0.057* | 0.481 (3) |
C5A | 0.3562 (5) | 0.0987 (4) | 0.3225 (6) | 0.0426 (10) | 0.481 (3) |
N1B | 0.3670 (4) | −0.1684 (4) | 0.3004 (3) | 0.0621 (12) | 0.519 (3) |
C1B | 0.4547 (3) | 0.0359 (3) | 0.3372 (3) | 0.0576 (9) | 0.519 (3) |
H1B | 0.5214 | 0.0821 | 0.3623 | 0.069* | 0.519 (3) |
C2B | 0.4580 (3) | −0.0948 (3) | 0.3349 (3) | 0.0686 (10) | 0.519 (3) |
H2B | 0.5284 | −0.1342 | 0.3590 | 0.082* | 0.519 (3) |
C3B | 0.2683 (5) | −0.1081 (6) | 0.2668 (5) | 0.0566 (5) | 0.519 (3) |
H3B | 0.2032 | −0.1571 | 0.2423 | 0.068* | 0.519 (3) |
C4B | 0.2554 (5) | 0.0232 (6) | 0.2657 (6) | 0.0472 (9) | 0.519 (3) |
H4B | 0.1838 | 0.0600 | 0.2412 | 0.057* | 0.519 (3) |
C5B | 0.3511 (5) | 0.0981 (4) | 0.3016 (5) | 0.0426 (10) | 0.519 (3) |
N2 | 0.45028 (10) | 0.29605 (11) | 0.35465 (9) | 0.0430 (3) | |
N3 | 0.78273 (12) | 0.58731 (14) | 0.49553 (11) | 0.0653 (4) | |
N4 | −0.00863 (12) | 0.63571 (15) | 0.22797 (11) | 0.0649 (4) | |
C6 | 0.35109 (12) | 0.23977 (13) | 0.30950 (11) | 0.0417 (4) | |
C7 | 0.25306 (13) | 0.30837 (13) | 0.26464 (11) | 0.0437 (4) | |
H7 | 0.1852 | 0.2666 | 0.2347 | 0.052* | |
C8 | 0.25806 (12) | 0.44026 (13) | 0.26527 (10) | 0.0407 (3) | |
C9 | 0.36080 (12) | 0.49770 (13) | 0.31145 (11) | 0.0455 (4) | |
H9 | 0.3668 | 0.5858 | 0.3129 | 0.055* | |
C10 | 0.45509 (12) | 0.42313 (13) | 0.35578 (10) | 0.0415 (4) | |
C11 | 0.56778 (12) | 0.47990 (13) | 0.40572 (11) | 0.0437 (4) | |
C12 | 0.58260 (14) | 0.60842 (15) | 0.42153 (14) | 0.0647 (5) | |
H12 | 0.5204 | 0.6630 | 0.4022 | 0.078* | |
C13 | 0.68941 (15) | 0.65634 (15) | 0.46600 (14) | 0.0690 (6) | |
H13 | 0.6961 | 0.7436 | 0.4759 | 0.083* | |
C14 | 0.76740 (15) | 0.46374 (17) | 0.48061 (14) | 0.0692 (6) | |
H14 | 0.8313 | 0.4117 | 0.5006 | 0.083* | |
C15 | 0.66450 (14) | 0.40636 (15) | 0.43787 (12) | 0.0577 (5) | |
H15 | 0.6601 | 0.3185 | 0.4307 | 0.069* | |
C16 | 0.15753 (12) | 0.52069 (13) | 0.21775 (11) | 0.0414 (4) | |
C17 | 0.08138 (14) | 0.55527 (16) | 0.26321 (12) | 0.0559 (4) | |
H17 | 0.0913 | 0.5216 | 0.3228 | 0.067* | |
C18 | −0.02300 (14) | 0.67870 (16) | 0.14256 (14) | 0.0582 (5) | |
H18 | −0.0838 | 0.7337 | 0.1174 | 0.070* | |
C19 | 0.04686 (13) | 0.64761 (13) | 0.08650 (12) | 0.0470 (4) | |
C20 | 0.02520 (16) | 0.69264 (15) | −0.00635 (13) | 0.0608 (5) | |
H20 | −0.0370 | 0.7454 | −0.0322 | 0.073* | |
C21 | 0.09424 (18) | 0.65955 (17) | −0.05793 (14) | 0.0693 (6) | |
H21 | 0.0788 | 0.6887 | −0.1193 | 0.083* | |
C22 | 0.18943 (17) | 0.58104 (19) | −0.01896 (14) | 0.0683 (5) | |
H22 | 0.2370 | 0.5594 | −0.0547 | 0.082* | |
C23 | 0.21254 (14) | 0.53651 (15) | 0.07018 (12) | 0.0545 (4) | |
H23 | 0.2760 | 0.4851 | 0.0950 | 0.065* | |
C24 | 0.14154 (12) | 0.56717 (13) | 0.12552 (11) | 0.0414 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0664 (11) | 0.0295 (8) | 0.087 (4) | 0.0014 (8) | 0.018 (2) | 0.0023 (16) |
C1A | 0.0477 (13) | 0.0334 (10) | 0.081 (3) | 0.0014 (9) | 0.0025 (19) | 0.0039 (17) |
C2A | 0.0590 (15) | 0.0343 (11) | 0.102 (3) | 0.0079 (11) | 0.009 (2) | 0.0080 (19) |
C3A | 0.0576 (15) | 0.0362 (8) | 0.0758 (16) | −0.0089 (11) | 0.0199 (12) | −0.0079 (9) |
C4A | 0.0453 (17) | 0.0341 (8) | 0.0621 (11) | −0.0025 (11) | 0.0159 (15) | −0.0025 (8) |
C5A | 0.0438 (10) | 0.0287 (7) | 0.054 (3) | 0.0007 (7) | 0.0125 (12) | 0.0015 (10) |
N1B | 0.0664 (11) | 0.0295 (8) | 0.087 (4) | 0.0014 (8) | 0.018 (2) | 0.0023 (16) |
C1B | 0.0477 (13) | 0.0334 (10) | 0.081 (3) | 0.0014 (9) | 0.0025 (19) | 0.0039 (17) |
C2B | 0.0590 (15) | 0.0343 (11) | 0.102 (3) | 0.0079 (11) | 0.009 (2) | 0.0080 (19) |
C3B | 0.0576 (15) | 0.0362 (8) | 0.0758 (16) | −0.0089 (11) | 0.0199 (12) | −0.0079 (9) |
C4B | 0.0453 (17) | 0.0341 (8) | 0.0621 (11) | −0.0025 (11) | 0.0159 (15) | −0.0025 (8) |
C5B | 0.0438 (10) | 0.0287 (7) | 0.054 (3) | 0.0007 (7) | 0.0125 (12) | 0.0015 (10) |
N2 | 0.0401 (7) | 0.0293 (6) | 0.0552 (8) | 0.0018 (5) | 0.0075 (6) | 0.0032 (5) |
N3 | 0.0470 (8) | 0.0558 (9) | 0.0770 (11) | −0.0053 (7) | −0.0055 (7) | −0.0067 (8) |
N4 | 0.0464 (8) | 0.0714 (10) | 0.0703 (11) | 0.0187 (7) | 0.0078 (7) | −0.0019 (8) |
C6 | 0.0409 (8) | 0.0280 (7) | 0.0547 (9) | −0.0003 (6) | 0.0123 (7) | 0.0014 (6) |
C7 | 0.0380 (8) | 0.0335 (7) | 0.0542 (9) | −0.0020 (6) | 0.0061 (7) | −0.0022 (7) |
C8 | 0.0399 (8) | 0.0330 (7) | 0.0456 (9) | 0.0022 (6) | 0.0073 (7) | 0.0022 (6) |
C9 | 0.0450 (9) | 0.0261 (7) | 0.0577 (10) | 0.0002 (6) | 0.0035 (7) | 0.0028 (6) |
C10 | 0.0402 (8) | 0.0301 (7) | 0.0483 (9) | 0.0003 (6) | 0.0044 (7) | 0.0021 (6) |
C11 | 0.0415 (8) | 0.0329 (7) | 0.0498 (9) | 0.0007 (6) | 0.0033 (7) | 0.0031 (6) |
C12 | 0.0471 (10) | 0.0338 (8) | 0.0939 (14) | 0.0008 (7) | −0.0082 (9) | 0.0016 (8) |
C13 | 0.0570 (11) | 0.0361 (9) | 0.0944 (15) | −0.0057 (8) | −0.0066 (10) | −0.0011 (9) |
C14 | 0.0469 (10) | 0.0536 (11) | 0.0879 (14) | 0.0082 (8) | −0.0087 (9) | −0.0096 (9) |
C15 | 0.0495 (9) | 0.0372 (8) | 0.0710 (12) | 0.0050 (7) | −0.0054 (8) | −0.0040 (8) |
C16 | 0.0357 (8) | 0.0298 (7) | 0.0520 (9) | −0.0006 (6) | 0.0027 (7) | −0.0013 (6) |
C17 | 0.0480 (9) | 0.0586 (10) | 0.0560 (10) | 0.0101 (8) | 0.0079 (8) | 0.0036 (8) |
C18 | 0.0407 (9) | 0.0491 (9) | 0.0716 (13) | 0.0102 (7) | −0.0031 (9) | −0.0010 (8) |
C19 | 0.0394 (8) | 0.0317 (7) | 0.0582 (10) | −0.0040 (6) | −0.0032 (7) | 0.0008 (7) |
C20 | 0.0561 (11) | 0.0442 (9) | 0.0645 (12) | −0.0062 (8) | −0.0083 (9) | 0.0106 (8) |
C21 | 0.0808 (14) | 0.0609 (11) | 0.0543 (11) | −0.0166 (10) | 0.0023 (10) | 0.0125 (9) |
C22 | 0.0742 (13) | 0.0700 (12) | 0.0611 (12) | −0.0085 (10) | 0.0210 (10) | 0.0013 (10) |
C23 | 0.0508 (10) | 0.0473 (9) | 0.0609 (11) | 0.0003 (8) | 0.0102 (8) | 0.0021 (8) |
C24 | 0.0366 (8) | 0.0282 (7) | 0.0520 (9) | −0.0037 (6) | 0.0021 (7) | −0.0015 (6) |
Geometric parameters (Å, º) top
N1A—C3A | 1.327 (3) | C7—H7 | 0.9300 |
N1A—C2A | 1.331 (3) | C8—C9 | 1.3829 (19) |
C1A—C2A | 1.376 (3) | C8—C16 | 1.4900 (19) |
C1A—C5A | 1.388 (3) | C9—C10 | 1.3915 (19) |
C1A—H1A | 0.9300 | C9—H9 | 0.9300 |
C2A—H2A | 0.9300 | C10—C11 | 1.4870 (19) |
C3A—C4A | 1.390 (3) | C11—C12 | 1.376 (2) |
C3A—H3A | 0.9300 | C11—C15 | 1.378 (2) |
C4A—C5A | 1.384 (3) | C12—C13 | 1.377 (2) |
C4A—H4A | 0.9300 | C12—H12 | 0.9300 |
C5A—C6 | 1.496 (4) | C13—H13 | 0.9300 |
N1B—C3B | 1.327 (3) | C14—C15 | 1.374 (2) |
N1B—C2B | 1.330 (3) | C14—H14 | 0.9300 |
C1B—C2B | 1.377 (3) | C15—H15 | 0.9300 |
C1B—C5B | 1.388 (3) | C16—C17 | 1.361 (2) |
C1B—H1B | 0.9300 | C16—C24 | 1.418 (2) |
C2B—H2B | 0.9300 | C17—H17 | 0.9300 |
C3B—C4B | 1.390 (3) | C18—C19 | 1.406 (2) |
C3B—H3B | 0.9300 | C18—H18 | 0.9300 |
C4B—C5B | 1.384 (3) | C19—C20 | 1.412 (2) |
C4B—H4B | 0.9300 | C19—C24 | 1.415 (2) |
C5B—C6 | 1.495 (4) | C20—C21 | 1.352 (3) |
N2—C10 | 1.3385 (17) | C20—H20 | 0.9300 |
N2—C6 | 1.3409 (18) | C21—C22 | 1.408 (3) |
N3—C13 | 1.317 (2) | C21—H21 | 0.9300 |
N3—C14 | 1.323 (2) | C22—C23 | 1.358 (2) |
N4—C18 | 1.313 (2) | C22—H22 | 0.9300 |
N4—C17 | 1.367 (2) | C23—C24 | 1.408 (2) |
C6—C7 | 1.3917 (19) | C23—H23 | 0.9300 |
C7—C8 | 1.3893 (18) | | |
| | | |
C3A—N1A—C2A | 115.75 (19) | C8—C9—H9 | 120.1 |
C2A—C1A—C5A | 119.5 (2) | C10—C9—H9 | 120.1 |
C2A—C1A—H1A | 120.2 | N2—C10—C9 | 122.02 (13) |
C5A—C1A—H1A | 120.2 | N2—C10—C11 | 116.02 (12) |
N1A—C2A—C1A | 124.3 (2) | C9—C10—C11 | 121.95 (12) |
N1A—C2A—H2A | 117.8 | C12—C11—C15 | 115.87 (14) |
C1A—C2A—H2A | 117.8 | C12—C11—C10 | 122.44 (13) |
N1A—C3A—C4A | 124.6 (2) | C15—C11—C10 | 121.68 (13) |
N1A—C3A—H3A | 117.7 | C11—C12—C13 | 120.06 (15) |
C4A—C3A—H3A | 117.7 | C11—C12—H12 | 120.0 |
C5A—C4A—C3A | 118.7 (2) | C13—C12—H12 | 120.0 |
C5A—C4A—H4A | 120.6 | N3—C13—C12 | 124.61 (15) |
C3A—C4A—H4A | 120.6 | N3—C13—H13 | 117.7 |
C4A—C5A—C1A | 117.05 (18) | C12—C13—H13 | 117.7 |
C4A—C5A—C6 | 120.3 (4) | N3—C14—C15 | 125.09 (16) |
C1A—C5A—C6 | 122.6 (4) | N3—C14—H14 | 117.5 |
C3B—N1B—C2B | 115.78 (19) | C15—C14—H14 | 117.5 |
C2B—C1B—C5B | 119.5 (2) | C14—C15—C11 | 119.51 (15) |
C2B—C1B—H1B | 120.3 | C14—C15—H15 | 120.2 |
C5B—C1B—H1B | 120.3 | C11—C15—H15 | 120.2 |
N1B—C2B—C1B | 124.3 (2) | C17—C16—C24 | 118.47 (14) |
N1B—C2B—H2B | 117.8 | C17—C16—C8 | 120.75 (14) |
C1B—C2B—H2B | 117.8 | C24—C16—C8 | 120.73 (13) |
N1B—C3B—C4B | 124.6 (2) | C16—C17—N4 | 124.94 (16) |
N1B—C3B—H3B | 117.7 | C16—C17—H17 | 117.5 |
C4B—C3B—H3B | 117.7 | N4—C17—H17 | 117.5 |
C5B—C4B—C3B | 118.7 (2) | N4—C18—C19 | 124.70 (15) |
C5B—C4B—H4B | 120.6 | N4—C18—H18 | 117.6 |
C3B—C4B—H4B | 120.6 | C19—C18—H18 | 117.6 |
C4B—C5B—C1B | 117.06 (18) | C18—C19—C20 | 122.49 (15) |
C4B—C5B—C6 | 125.3 (4) | C18—C19—C24 | 117.94 (15) |
C1B—C5B—C6 | 117.5 (4) | C20—C19—C24 | 119.57 (16) |
C10—N2—C6 | 118.54 (12) | C21—C20—C19 | 120.47 (17) |
C13—N3—C14 | 114.84 (14) | C21—C20—H20 | 119.8 |
C18—N4—C17 | 116.34 (15) | C19—C20—H20 | 119.8 |
N2—C6—C7 | 122.54 (12) | C20—C21—C22 | 120.16 (18) |
N2—C6—C5B | 117.3 (2) | C20—C21—H21 | 119.9 |
C7—C6—C5B | 120.0 (2) | C22—C21—H21 | 119.9 |
N2—C6—C5A | 112.1 (2) | C23—C22—C21 | 120.69 (19) |
C7—C6—C5A | 125.0 (3) | C23—C22—H22 | 119.7 |
C8—C7—C6 | 119.00 (13) | C21—C22—H22 | 119.7 |
C8—C7—H7 | 120.5 | C22—C23—C24 | 120.79 (16) |
C6—C7—H7 | 120.5 | C22—C23—H23 | 119.6 |
C9—C8—C7 | 118.17 (13) | C24—C23—H23 | 119.6 |
C9—C8—C16 | 119.44 (12) | C23—C24—C19 | 118.31 (15) |
C7—C8—C16 | 122.39 (13) | C23—C24—C16 | 124.14 (14) |
C8—C9—C10 | 119.73 (13) | C19—C24—C16 | 117.54 (14) |
| | | |
C3A—N1A—C2A—C1A | 0.0 (3) | N2—C10—C11—C12 | −172.69 (16) |
C5A—C1A—C2A—N1A | 0.0 (3) | C9—C10—C11—C12 | 8.4 (3) |
C2A—N1A—C3A—C4A | −0.1 (6) | N2—C10—C11—C15 | 8.3 (2) |
N1A—C3A—C4A—C5A | 0.2 (8) | C9—C10—C11—C15 | −170.61 (16) |
C3A—C4A—C5A—C1A | −0.2 (7) | C15—C11—C12—C13 | 0.8 (3) |
C3A—C4A—C5A—C6 | 178.0 (6) | C10—C11—C12—C13 | −178.31 (17) |
C2A—C1A—C5A—C4A | 0.1 (6) | C14—N3—C13—C12 | −0.9 (3) |
C2A—C1A—C5A—C6 | −178.1 (6) | C11—C12—C13—N3 | 0.4 (3) |
C3B—N1B—C2B—C1B | −0.1 (3) | C13—N3—C14—C15 | 0.2 (3) |
C5B—C1B—C2B—N1B | −0.1 (3) | N3—C14—C15—C11 | 1.0 (3) |
C2B—N1B—C3B—C4B | 0.1 (6) | C12—C11—C15—C14 | −1.4 (3) |
N1B—C3B—C4B—C5B | 0.1 (7) | C10—C11—C15—C14 | 177.67 (16) |
C3B—C4B—C5B—C1B | −0.2 (7) | C9—C8—C16—C17 | −93.49 (19) |
C3B—C4B—C5B—C6 | −177.1 (6) | C7—C8—C16—C17 | 86.92 (19) |
C2B—C1B—C5B—C4B | 0.2 (5) | C9—C8—C16—C24 | 83.94 (18) |
C2B—C1B—C5B—C6 | 177.4 (5) | C7—C8—C16—C24 | −95.65 (18) |
C10—N2—C6—C7 | −0.6 (2) | C24—C16—C17—N4 | −2.3 (2) |
C10—N2—C6—C5B | 174.4 (4) | C8—C16—C17—N4 | 175.22 (15) |
C10—N2—C6—C5A | −174.3 (4) | C18—N4—C17—C16 | 2.1 (3) |
C4B—C5B—C6—N2 | 173.5 (4) | C17—N4—C18—C19 | 0.1 (3) |
C1B—C5B—C6—N2 | −3.3 (7) | N4—C18—C19—C20 | 177.54 (16) |
C4B—C5B—C6—C7 | −11.4 (6) | N4—C18—C19—C24 | −1.9 (2) |
C1B—C5B—C6—C7 | 171.7 (4) | C18—C19—C20—C21 | −179.53 (15) |
C4A—C5A—C6—N2 | −162.9 (4) | C24—C19—C20—C21 | −0.1 (2) |
C1A—C5A—C6—N2 | 15.2 (8) | C19—C20—C21—C22 | −0.8 (3) |
C4A—C5A—C6—C7 | 23.5 (7) | C20—C21—C22—C23 | 0.7 (3) |
C1A—C5A—C6—C7 | −158.4 (4) | C21—C22—C23—C24 | 0.4 (3) |
N2—C6—C7—C8 | 0.9 (2) | C22—C23—C24—C19 | −1.2 (2) |
C5B—C6—C7—C8 | −173.8 (4) | C22—C23—C24—C16 | 177.57 (15) |
C5A—C6—C7—C8 | 173.9 (4) | C18—C19—C24—C23 | −179.42 (14) |
C6—C7—C8—C9 | −0.5 (2) | C20—C19—C24—C23 | 1.1 (2) |
C6—C7—C8—C16 | 179.09 (14) | C18—C19—C24—C16 | 1.68 (19) |
C7—C8—C9—C10 | −0.2 (2) | C20—C19—C24—C16 | −177.80 (13) |
C16—C8—C9—C10 | −179.84 (14) | C17—C16—C24—C23 | −178.59 (14) |
C6—N2—C10—C9 | −0.2 (2) | C8—C16—C24—C23 | 3.9 (2) |
C6—N2—C10—C11 | −179.12 (13) | C17—C16—C24—C19 | 0.2 (2) |
C8—C9—C10—N2 | 0.6 (2) | C8—C16—C24—C19 | −177.25 (12) |
C8—C9—C10—C11 | 179.46 (15) | | |
Crystal data top
C24H16N4 | F(000) = 752 |
Mr = 360.41 | Dx = 1.296 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3277 (3) Å | Cell parameters from 2812 reflections |
b = 10.5211 (2) Å | θ = 4.2–26.1° |
c = 14.9441 (4) Å | µ = 0.08 mm−1 |
β = 107.638 (2)° | T = 293 K |
V = 1847.15 (8) Å3 | Plate, colourless |
Z = 4 | 0.28 × 0.20 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 3785 independent reflections |
Radiation source: fine-focus sealed tube | 2672 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans, thick slices | θmax = 26.4°, θmin = 3.8° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | h = −15→15 |
| k = −13→13 |
36721 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2691P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.134 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.16 e Å−3 |
3785 reflections | Δρmin = −0.14 e Å−3 |
273 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
19 restraints | Extinction coefficient: 0.0037 (9) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1A | 0.3653 (5) | −0.1667 (4) | 0.3411 (4) | 0.0689 (13) | 0.468 (3) |
C1A | 0.4409 (4) | 0.0396 (3) | 0.3908 (3) | 0.0638 (10) | 0.468 (3) |
H1A | 0.4978 | 0.0874 | 0.4322 | 0.077* | 0.468 (3) |
C2A | 0.4425 (4) | −0.0906 (3) | 0.3970 (4) | 0.0777 (11) | 0.468 (3) |
H2A | 0.5018 | −0.1281 | 0.4435 | 0.093* | 0.468 (3) |
C3A | 0.2827 (5) | −0.1088 (6) | 0.2761 (6) | 0.0628 (6) | 0.468 (3) |
H3A | 0.2273 | −0.1594 | 0.2357 | 0.075* | 0.468 (3) |
C4A | 0.2729 (5) | 0.0219 (6) | 0.2638 (7) | 0.0532 (8) | 0.468 (3) |
H4A | 0.2126 | 0.0568 | 0.2167 | 0.064* | 0.468 (3) |
C5A | 0.3542 (6) | 0.0993 (4) | 0.3227 (6) | 0.0464 (11) | 0.468 (3) |
N1B | 0.3670 (4) | −0.1678 (3) | 0.3012 (3) | 0.0689 (13) | 0.532 (3) |
C1B | 0.4546 (3) | 0.0360 (3) | 0.3383 (3) | 0.0638 (10) | 0.532 (3) |
H1B | 0.5213 | 0.0818 | 0.3641 | 0.077* | 0.532 (3) |
C2B | 0.4574 (3) | −0.0944 (3) | 0.3362 (3) | 0.0777 (11) | 0.532 (3) |
H2B | 0.5275 | −0.1341 | 0.3610 | 0.093* | 0.532 (3) |
C3B | 0.2691 (5) | −0.1070 (5) | 0.2666 (5) | 0.0628 (6) | 0.532 (3) |
H3B | 0.2040 | −0.1556 | 0.2414 | 0.075* | 0.532 (3) |
C4B | 0.2568 (5) | 0.0242 (6) | 0.2653 (6) | 0.0532 (8) | 0.532 (3) |
H4B | 0.1855 | 0.0612 | 0.2403 | 0.064* | 0.532 (3) |
C5B | 0.3522 (5) | 0.0988 (3) | 0.3018 (5) | 0.0464 (11) | 0.532 (3) |
N2 | 0.44956 (10) | 0.29652 (11) | 0.35423 (9) | 0.0470 (3) | |
N3 | 0.78162 (12) | 0.58724 (15) | 0.49535 (11) | 0.0712 (5) | |
N4 | −0.00844 (12) | 0.63545 (15) | 0.22770 (12) | 0.0707 (4) | |
C6 | 0.35057 (12) | 0.24028 (13) | 0.30931 (11) | 0.0454 (4) | |
C7 | 0.25286 (13) | 0.30885 (13) | 0.26450 (11) | 0.0478 (4) | |
H7 | 0.1851 | 0.2671 | 0.2346 | 0.057* | |
C8 | 0.25796 (12) | 0.44063 (13) | 0.26505 (10) | 0.0443 (4) | |
C9 | 0.36036 (12) | 0.49813 (14) | 0.31107 (11) | 0.0497 (4) | |
H9 | 0.3664 | 0.5863 | 0.3126 | 0.060* | |
C10 | 0.45456 (12) | 0.42338 (13) | 0.35510 (10) | 0.0453 (4) | |
C11 | 0.56710 (12) | 0.48021 (13) | 0.40540 (11) | 0.0478 (4) | |
C12 | 0.58213 (14) | 0.60848 (15) | 0.42105 (14) | 0.0700 (6) | |
H12 | 0.5201 | 0.6632 | 0.4015 | 0.084* | |
C13 | 0.68849 (16) | 0.65627 (16) | 0.46557 (15) | 0.0747 (6) | |
H13 | 0.6952 | 0.7436 | 0.4754 | 0.090* | |
C14 | 0.76617 (15) | 0.46407 (18) | 0.48051 (15) | 0.0757 (6) | |
H14 | 0.8298 | 0.4119 | 0.5007 | 0.091* | |
C15 | 0.66344 (14) | 0.40673 (16) | 0.43754 (13) | 0.0638 (5) | |
H15 | 0.6591 | 0.3189 | 0.4302 | 0.077* | |
C16 | 0.15736 (12) | 0.52117 (13) | 0.21745 (11) | 0.0456 (4) | |
C17 | 0.08147 (14) | 0.55557 (17) | 0.26294 (13) | 0.0610 (5) | |
H17 | 0.0917 | 0.5221 | 0.3225 | 0.073* | |
C18 | −0.02300 (14) | 0.67862 (16) | 0.14272 (14) | 0.0642 (5) | |
H18 | −0.0838 | 0.7334 | 0.1176 | 0.077* | |
C19 | 0.04658 (13) | 0.64823 (13) | 0.08658 (12) | 0.0514 (4) | |
C20 | 0.02494 (16) | 0.69315 (16) | −0.00617 (14) | 0.0662 (5) | |
H20 | −0.0372 | 0.7459 | −0.0320 | 0.079* | |
C21 | 0.0932 (2) | 0.66045 (19) | −0.05777 (15) | 0.0771 (6) | |
H21 | 0.0773 | 0.6895 | −0.1192 | 0.093* | |
C22 | 0.18862 (18) | 0.5824 (2) | −0.01892 (14) | 0.0746 (5) | |
H22 | 0.2361 | 0.5613 | −0.0546 | 0.090* | |
C23 | 0.21210 (14) | 0.53746 (16) | 0.07032 (13) | 0.0593 (4) | |
H23 | 0.2756 | 0.4862 | 0.0951 | 0.071* | |
C24 | 0.14117 (12) | 0.56782 (13) | 0.12552 (11) | 0.0455 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0742 (12) | 0.0328 (8) | 0.096 (4) | 0.0015 (8) | 0.021 (2) | 0.0026 (15) |
C1A | 0.0519 (14) | 0.0358 (10) | 0.092 (3) | 0.0034 (9) | 0.003 (2) | 0.0022 (17) |
C2A | 0.0667 (17) | 0.0382 (12) | 0.117 (3) | 0.0084 (11) | 0.011 (2) | 0.005 (2) |
C3A | 0.0653 (15) | 0.0403 (9) | 0.0813 (17) | −0.0104 (10) | 0.0199 (12) | −0.0078 (10) |
C4A | 0.0515 (15) | 0.0373 (8) | 0.0691 (12) | −0.0022 (9) | 0.0155 (14) | −0.0016 (8) |
C5A | 0.0475 (9) | 0.0321 (8) | 0.059 (3) | 0.0006 (6) | 0.0151 (13) | 0.0017 (9) |
N1B | 0.0742 (12) | 0.0328 (8) | 0.096 (4) | 0.0015 (8) | 0.021 (2) | 0.0026 (15) |
C1B | 0.0519 (14) | 0.0358 (10) | 0.092 (3) | 0.0034 (9) | 0.003 (2) | 0.0022 (17) |
C2B | 0.0667 (17) | 0.0382 (12) | 0.117 (3) | 0.0084 (11) | 0.011 (2) | 0.005 (2) |
C3B | 0.0653 (15) | 0.0403 (9) | 0.0813 (17) | −0.0104 (10) | 0.0199 (12) | −0.0078 (10) |
C4B | 0.0515 (15) | 0.0373 (8) | 0.0691 (12) | −0.0022 (9) | 0.0155 (14) | −0.0016 (8) |
C5B | 0.0475 (9) | 0.0321 (8) | 0.059 (3) | 0.0006 (6) | 0.0151 (13) | 0.0017 (9) |
N2 | 0.0432 (7) | 0.0323 (6) | 0.0602 (8) | 0.0015 (5) | 0.0075 (6) | 0.0027 (5) |
N3 | 0.0487 (9) | 0.0617 (9) | 0.0862 (11) | −0.0053 (7) | −0.0049 (8) | −0.0060 (8) |
N4 | 0.0494 (9) | 0.0792 (11) | 0.0766 (11) | 0.0209 (7) | 0.0086 (8) | −0.0020 (9) |
C6 | 0.0440 (8) | 0.0313 (7) | 0.0580 (9) | −0.0002 (6) | 0.0113 (7) | 0.0002 (6) |
C7 | 0.0404 (8) | 0.0361 (8) | 0.0613 (10) | −0.0026 (6) | 0.0069 (7) | −0.0021 (7) |
C8 | 0.0407 (8) | 0.0367 (7) | 0.0507 (9) | 0.0037 (6) | 0.0069 (7) | 0.0027 (6) |
C9 | 0.0465 (9) | 0.0305 (7) | 0.0645 (10) | 0.0016 (6) | 0.0053 (8) | 0.0033 (7) |
C10 | 0.0424 (8) | 0.0326 (7) | 0.0546 (9) | 0.0001 (6) | 0.0051 (7) | 0.0013 (6) |
C11 | 0.0430 (8) | 0.0377 (8) | 0.0551 (9) | 0.0006 (6) | 0.0033 (7) | 0.0037 (7) |
C12 | 0.0480 (10) | 0.0380 (9) | 0.1037 (15) | 0.0007 (7) | −0.0076 (9) | 0.0014 (9) |
C13 | 0.0593 (11) | 0.0418 (9) | 0.1030 (16) | −0.0074 (8) | −0.0052 (11) | −0.0018 (9) |
C14 | 0.0483 (10) | 0.0606 (11) | 0.0971 (15) | 0.0086 (8) | −0.0097 (10) | −0.0096 (10) |
C15 | 0.0513 (10) | 0.0419 (9) | 0.0812 (13) | 0.0054 (7) | −0.0052 (9) | −0.0026 (8) |
C16 | 0.0379 (8) | 0.0353 (7) | 0.0569 (9) | 0.0005 (6) | 0.0041 (7) | −0.0015 (7) |
C17 | 0.0513 (10) | 0.0644 (11) | 0.0618 (11) | 0.0112 (8) | 0.0086 (8) | 0.0040 (8) |
C18 | 0.0436 (9) | 0.0556 (10) | 0.0795 (13) | 0.0116 (7) | −0.0020 (9) | −0.0019 (9) |
C19 | 0.0433 (9) | 0.0360 (8) | 0.0617 (10) | −0.0033 (6) | −0.0040 (7) | 0.0018 (7) |
C20 | 0.0612 (11) | 0.0501 (10) | 0.0686 (12) | −0.0066 (8) | −0.0085 (10) | 0.0111 (9) |
C21 | 0.0881 (15) | 0.0691 (13) | 0.0603 (12) | −0.0190 (11) | 0.0017 (11) | 0.0143 (10) |
C22 | 0.0801 (14) | 0.0786 (13) | 0.0654 (12) | −0.0090 (11) | 0.0223 (11) | 0.0040 (10) |
C23 | 0.0546 (10) | 0.0527 (10) | 0.0667 (11) | −0.0004 (8) | 0.0122 (9) | 0.0010 (8) |
C24 | 0.0400 (8) | 0.0319 (7) | 0.0567 (9) | −0.0042 (6) | 0.0026 (7) | −0.0016 (6) |
Geometric parameters (Å, º) top
N1A—C3A | 1.324 (3) | C7—H7 | 0.9300 |
N1A—C2A | 1.327 (3) | C8—C9 | 1.381 (2) |
C1A—C2A | 1.373 (3) | C8—C16 | 1.4925 (19) |
C1A—C5A | 1.382 (3) | C9—C10 | 1.3917 (19) |
C1A—H1A | 0.9300 | C9—H9 | 0.9300 |
C2A—H2A | 0.9300 | C10—C11 | 1.4884 (19) |
C3A—C4A | 1.388 (3) | C11—C12 | 1.373 (2) |
C3A—H3A | 0.9300 | C11—C15 | 1.376 (2) |
C4A—C5A | 1.382 (3) | C12—C13 | 1.373 (2) |
C4A—H4A | 0.9300 | C12—H12 | 0.9300 |
C5A—C6 | 1.496 (4) | C13—H13 | 0.9300 |
N1B—C3B | 1.324 (3) | C14—C15 | 1.374 (2) |
N1B—C2B | 1.326 (3) | C14—H14 | 0.9300 |
C1B—C2B | 1.373 (3) | C15—H15 | 0.9300 |
C1B—C5B | 1.383 (3) | C16—C17 | 1.361 (2) |
C1B—H1B | 0.9300 | C16—C24 | 1.415 (2) |
C2B—H2B | 0.9300 | C17—H17 | 0.9300 |
C3B—C4B | 1.387 (3) | C18—C19 | 1.407 (3) |
C3B—H3B | 0.9300 | C18—H18 | 0.9300 |
C4B—C5B | 1.381 (3) | C19—C20 | 1.411 (2) |
C4B—H4B | 0.9300 | C19—C24 | 1.415 (2) |
C5B—C6 | 1.494 (4) | C20—C21 | 1.347 (3) |
N2—C10 | 1.3360 (17) | C20—H20 | 0.9300 |
N2—C6 | 1.3392 (18) | C21—C22 | 1.408 (3) |
N3—C13 | 1.317 (2) | C21—H21 | 0.9300 |
N3—C14 | 1.319 (2) | C22—C23 | 1.361 (3) |
N4—C18 | 1.309 (2) | C22—H22 | 0.9300 |
N4—C17 | 1.363 (2) | C23—C24 | 1.409 (2) |
C6—C7 | 1.390 (2) | C23—H23 | 0.9300 |
C7—C8 | 1.3879 (19) | | |
| | | |
C3A—N1A—C2A | 115.5 (2) | C8—C9—H9 | 120.2 |
C2A—C1A—C5A | 119.7 (2) | C10—C9—H9 | 120.2 |
C2A—C1A—H1A | 120.2 | N2—C10—C9 | 122.04 (13) |
C5A—C1A—H1A | 120.2 | N2—C10—C11 | 116.07 (12) |
N1A—C2A—C1A | 124.5 (2) | C9—C10—C11 | 121.89 (13) |
N1A—C2A—H2A | 117.8 | C12—C11—C15 | 115.80 (14) |
C1A—C2A—H2A | 117.8 | C12—C11—C10 | 122.55 (13) |
N1A—C3A—C4A | 124.7 (2) | C15—C11—C10 | 121.63 (13) |
N1A—C3A—H3A | 117.6 | C11—C12—C13 | 120.15 (16) |
C4A—C3A—H3A | 117.6 | C11—C12—H12 | 119.9 |
C5A—C4A—C3A | 118.8 (2) | C13—C12—H12 | 119.9 |
C5A—C4A—H4A | 120.6 | N3—C13—C12 | 124.64 (16) |
C3A—C4A—H4A | 120.6 | N3—C13—H13 | 117.7 |
C4A—C5A—C1A | 116.80 (19) | C12—C13—H13 | 117.7 |
C4A—C5A—C6 | 120.8 (4) | N3—C14—C15 | 125.16 (16) |
C1A—C5A—C6 | 122.3 (4) | N3—C14—H14 | 117.4 |
C3B—N1B—C2B | 115.49 (19) | C15—C14—H14 | 117.4 |
C2B—C1B—C5B | 119.6 (2) | C14—C15—C11 | 119.49 (15) |
C2B—C1B—H1B | 120.2 | C14—C15—H15 | 120.3 |
C5B—C1B—H1B | 120.2 | C11—C15—H15 | 120.3 |
N1B—C2B—C1B | 124.6 (2) | C17—C16—C24 | 118.46 (14) |
N1B—C2B—H2B | 117.7 | C17—C16—C8 | 120.70 (14) |
C1B—C2B—H2B | 117.7 | C24—C16—C8 | 120.80 (13) |
N1B—C3B—C4B | 124.7 (2) | C16—C17—N4 | 124.91 (17) |
N1B—C3B—H3B | 117.7 | C16—C17—H17 | 117.5 |
C4B—C3B—H3B | 117.7 | N4—C17—H17 | 117.5 |
C5B—C4B—C3B | 118.9 (2) | N4—C18—C19 | 124.80 (15) |
C5B—C4B—H4B | 120.6 | N4—C18—H18 | 117.6 |
C3B—C4B—H4B | 120.6 | C19—C18—H18 | 117.6 |
C4B—C5B—C1B | 116.82 (18) | C18—C19—C20 | 122.81 (16) |
C4B—C5B—C6 | 124.6 (4) | C18—C19—C24 | 117.78 (15) |
C1B—C5B—C6 | 118.5 (4) | C20—C19—C24 | 119.41 (16) |
C10—N2—C6 | 118.59 (12) | C21—C20—C19 | 120.78 (18) |
C13—N3—C14 | 114.74 (15) | C21—C20—H20 | 119.6 |
C18—N4—C17 | 116.44 (15) | C19—C20—H20 | 119.6 |
N2—C6—C7 | 122.51 (13) | C20—C21—C22 | 120.12 (18) |
N2—C6—C5B | 116.6 (2) | C20—C21—H21 | 119.9 |
C7—C6—C5B | 120.7 (2) | C22—C21—H21 | 119.9 |
N2—C6—C5A | 112.6 (3) | C23—C22—C21 | 120.65 (19) |
C7—C6—C5A | 124.5 (3) | C23—C22—H22 | 119.7 |
C8—C7—C6 | 118.99 (13) | C21—C22—H22 | 119.7 |
C8—C7—H7 | 120.5 | C22—C23—C24 | 120.64 (17) |
C6—C7—H7 | 120.5 | C22—C23—H23 | 119.7 |
C9—C8—C7 | 118.27 (13) | C24—C23—H23 | 119.7 |
C9—C8—C16 | 119.40 (12) | C23—C24—C16 | 124.06 (14) |
C7—C8—C16 | 122.33 (13) | C23—C24—C19 | 118.37 (15) |
C8—C9—C10 | 119.59 (13) | C16—C24—C19 | 117.57 (14) |
| | | |
C3A—N1A—C2A—C1A | 0.0 (3) | N2—C10—C11—C12 | −172.62 (17) |
C5A—C1A—C2A—N1A | 0.1 (3) | C9—C10—C11—C12 | 7.8 (3) |
C2A—N1A—C3A—C4A | −0.1 (6) | N2—C10—C11—C15 | 8.7 (2) |
N1A—C3A—C4A—C5A | 0.1 (8) | C9—C10—C11—C15 | −170.88 (16) |
C3A—C4A—C5A—C1A | 0.0 (7) | C15—C11—C12—C13 | 0.5 (3) |
C3A—C4A—C5A—C6 | 177.0 (7) | C10—C11—C12—C13 | −178.19 (17) |
C2A—C1A—C5A—C4A | −0.1 (6) | C14—N3—C13—C12 | −0.9 (3) |
C2A—C1A—C5A—C6 | −177.0 (6) | C11—C12—C13—N3 | 0.5 (3) |
C3B—N1B—C2B—C1B | 0.0 (3) | C13—N3—C14—C15 | 0.2 (3) |
C5B—C1B—C2B—N1B | −0.2 (3) | N3—C14—C15—C11 | 0.8 (3) |
C2B—N1B—C3B—C4B | −0.1 (6) | C12—C11—C15—C14 | −1.1 (3) |
N1B—C3B—C4B—C5B | 0.4 (7) | C10—C11—C15—C14 | 177.61 (17) |
C3B—C4B—C5B—C1B | −0.5 (7) | C9—C8—C16—C17 | −93.60 (19) |
C3B—C4B—C5B—C6 | −176.8 (6) | C7—C8—C16—C17 | 86.8 (2) |
C2B—C1B—C5B—C4B | 0.5 (5) | C9—C8—C16—C24 | 83.78 (18) |
C2B—C1B—C5B—C6 | 177.0 (5) | C7—C8—C16—C24 | −95.87 (18) |
C10—N2—C6—C7 | −0.7 (2) | C24—C16—C17—N4 | −2.0 (3) |
C10—N2—C6—C5B | 173.9 (4) | C8—C16—C17—N4 | 175.44 (15) |
C10—N2—C6—C5A | −173.9 (4) | C18—N4—C17—C16 | 1.8 (3) |
C4B—C5B—C6—N2 | 174.1 (4) | C17—N4—C18—C19 | 0.2 (3) |
C1B—C5B—C6—N2 | −2.1 (7) | N4—C18—C19—C20 | 177.42 (16) |
C4B—C5B—C6—C7 | −11.2 (6) | N4—C18—C19—C24 | −1.8 (3) |
C1B—C5B—C6—C7 | 172.6 (4) | C18—C19—C20—C21 | −179.26 (16) |
C4A—C5A—C6—N2 | −162.9 (5) | C24—C19—C20—C21 | −0.1 (2) |
C1A—C5A—C6—N2 | 13.8 (8) | C19—C20—C21—C22 | −1.1 (3) |
C4A—C5A—C6—C7 | 24.0 (7) | C20—C21—C22—C23 | 1.0 (3) |
C1A—C5A—C6—C7 | −159.2 (5) | C21—C22—C23—C24 | 0.2 (3) |
N2—C6—C7—C8 | 0.9 (2) | C22—C23—C24—C16 | 177.56 (16) |
C5B—C6—C7—C8 | −173.5 (4) | C22—C23—C24—C19 | −1.3 (2) |
C5A—C6—C7—C8 | 173.3 (5) | C17—C16—C24—C23 | −178.72 (15) |
C6—C7—C8—C9 | −0.5 (2) | C8—C16—C24—C23 | 3.8 (2) |
C6—C7—C8—C16 | 179.13 (14) | C17—C16—C24—C19 | 0.2 (2) |
C7—C8—C9—C10 | 0.0 (2) | C8—C16—C24—C19 | −177.23 (13) |
C16—C8—C9—C10 | −179.64 (14) | C18—C19—C24—C23 | −179.49 (14) |
C6—N2—C10—C9 | 0.1 (2) | C20—C19—C24—C23 | 1.3 (2) |
C6—N2—C10—C11 | −179.47 (13) | C18—C19—C24—C16 | 1.5 (2) |
C8—C9—C10—N2 | 0.2 (2) | C20—C19—C24—C16 | −177.72 (14) |
C8—C9—C10—C11 | 179.77 (15) | | |