A temperature-induced order–disorder phase transition in a 4-substituted 4,2′:6′,4′′-terpyridine

Granifo, J.; Westermeyer, M.; Riquelme, M.; Gaviño, R.; Suárez, S.; Halac, E.B.; Baggio, R.

doi:10.1107/S205252061501937X

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A temperature-induced order–disorder phase transition in a 4-substituted 4,2′:6′,4′′-terpyridine

J. Granifo, M. Westermeyer, M. Riquelme, R. Gaviño, S. Suárez, E. B. Halac and R. Baggio

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 T_c 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.

Keywords: phase transition; first order; ligand properties; weak interactions; order–disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061501937X/eb5043sup1.cif Contains datablocks 170, 220, 274, 277, 293, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061501937X/eb5043170sup2.hkl Contains datablock 170
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061501937X/eb5043220sup3.hkl Contains datablock 220
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061501937X/eb5043274sup4.hkl Contains datablock 274
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061501937X/eb5043277sup5.hkl Contains datablock 277
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061501937X/eb5043293sup6.hkl Contains datablock 293
	Portable Document Format (PDF) file https://doi.org/10.1107/S205252061501937X/eb5043sup7.pdf Tables of bond distances and angles

CCDC references: 1430999; 1431000; 1431001; 1431002; 1431003

Computing details top

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).

(170) top

Crystal data top

C₂₄H₁₆N₄	F(000) = 1504
M_r = 360.41	D_x = 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	R_int = 0.056
ω scans, thick slices	θ_max = 26.4°, θ_min = 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(F_o²) + (0.0685P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
7341 reflections	Δρ_max = 0.23 e Å⁻³
506 parameters	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

(220) top

Crystal data top

C₂₄H₁₆N₄	F(000) = 1504
M_r = 360.41	D_x = 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	R_int = 0.058
ω scans, thick slices	θ_max = 26.4°, θ_min = 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(F_o²) + (0.0685P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
7397 reflections	Δρ_max = 0.18 e Å⁻³
506 parameters	Δρ_min = −0.18 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

(274) top

Crystal data top

C₂₄H₁₆N₄	F(000) = 1504
M_r = 360.41	D_x = 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	R_int = 0.060
ω scans, thick slices	θ_max = 26.4°, θ_min = 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(F_o²) + (0.0685P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
7461 reflections	Δρ_max = 0.39 e Å⁻³
506 parameters	Δρ_min = −0.21 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

(277) top

Crystal data top

C₂₄H₁₆N₄	F(000) = 752
M_r = 360.41	D_x = 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	R_int = 0.048
ω scans, thick slices	θ_max = 26.4°, θ_min = 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(F_o²) + (0.0496P)² + 0.3259P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3773 reflections	Δρ_max = 0.14 e Å⁻³
272 parameters	Δρ_min = −0.15 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

(293) top

Crystal data top

C₂₄H₁₆N₄	F(000) = 752
M_r = 360.41	D_x = 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	R_int = 0.059
ω scans, thick slices	θ_max = 26.4°, θ_min = 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(F_o²) + (0.0588P)² + 0.2691P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.134	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.16 e Å⁻³
3785 reflections	Δρ_min = −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	U_iso*/U_eq	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)

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