4′-(4-Methyl­phen­yl)-2,2′:6′,2′′-terpyridine

Liu, H.-G.; Qiu, Y.-C.; Wu, J.-Z.

doi:10.1107/S1600536807060904

4′-(4-Methylphenyl)-2,2′:6′,2′′-terpyridine

There are two crystallographically independent molecules in the asymmetric unit of the title compound, C₂₂H₁₇N₃. In each molecule, the three pyridyl groups are nearly coplanar, whereas the tolyl groups are twisted out of the plane of the attached pyridyl rings by ca 28°. The molecular components are assembled through C—H

π and π–π interactions [centroid–centroid distances are 3.677 (4) and 3.707 (7) Å] into a one-dimensional chain running in the a-axis direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060904/kj2073sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060904/kj2073Isup2.hkl Contains datablock I

CCDC reference: 673065

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.048
wR factor = 0.131
Data-to-parameter ratio = 17.7

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Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Organic molecules bearing the 2,2':6',2"-terpyridine (ttp) group have a geometry favourable for accepting various metal centres, therefore such molecules are used widely in coordination chemistry (Samnes & Yahioglu, 1994; Thummel, 2004; Cargill Thompson, 1997). However, the crystal structure of the title compound has not been reported until now.

As illustrated in Fig. 1, in an asymmetric unit there are two crystallographically independent molecules, which are slightly distinct. In each molecule the three pyridyl moieties are nearly coplanar. The tolyl groups are twisted out of their connected pyridyls by 28.7 (4)° and 27.8 (9)°, respectively, which is somewhat different from the values reported for [Mn(ttp)₂](ClO₄)₂ [35.62 (4)° and 20.23 (6), Liu et al. (2007)]. In the asymmetric unit, the two terpyridyl moieties are parellel and staggered, whereas the two benzene rings make a dihedral angle of 55.6 (5)°. The crystal packing involves three short C—H···π contacts. A list, with geometric details, is given in Table 1. THe crystal packing also involves π-π stacking for some pyridyl rings: the centroid-centroid distances are 3.677 (4) Å between ring(N2, C6—C10) and ring(N4, C23—C27), and 3.707 (7) Å between ring(N3, C11—C15) and ring(N5, C28—C32)[-1 + x, y, z]. The C—H···π and π-π stacking interactions join the molecules into a one-dimensional chain, running in the a-direction (Fig. 2).

Related literature top

For related literature, see Cargill Thompson (1997); Collin et al. (1991); Liu et al. (2007); Thummel (2004); Wang et al. (2007); Samnes & Yahioglu (1994). Cg1 and Cg2 are the centroids of rings C38–C43 and C16–C21, respectively.

Experimental top

4'-(4-methylphenyl)-2,2':6',2"-terpyridine (ttp) was prepared by an improved Kröhnke condensation method (Wang et al., 2007; Collin et al., 1991). A mixture of ttp (2 mmol) and water/ethanol(10 ml, 1:1) was placed in a 25 ml of Teflon-lined stainless steel vessel and heated under autogenous pressure at 413 K for 3 days, followed by cooling to room temperature at a rate of 5 K/h. Colorless block crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTLXP (Bruker, 2004).

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing view of (I). C—H···π and π···π interactions are shown as dashed lines. H atoms not involved in close contacts are omitted for clarity.

4'-(4-Methylphenyl)-2,2':6',2''-terpyridine top

Crystal data top

C₂₂H₁₇N₃	F(000) = 1360
M_r = 323.39	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5600 reflections
a = 9.4575 (4) Å	θ = 1.4–28.0°
b = 33.8005 (15) Å	µ = 0.08 mm⁻¹
c = 11.3730 (5) Å	T = 293 K
β = 112.357 (3)°	Block, colourless
V = 3362.3 (3) Å³	0.26 × 0.23 × 0.19 mm
Z = 8

Data collection top

Bruker APEXII area-detector diffractometer	4866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 27.9°, θ_min = 2.0°
ϕ and ω scan	h = −12→12
54997 measured reflections	k = −44→43
8020 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0511P)² + 0.4806P] where P = (F_o² + 2F_c²)/3
8020 reflections	(Δ/σ)_max < 0.001
453 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₁₇N₃	V = 3362.3 (3) Å³
M_r = 323.39	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4575 (4) Å	µ = 0.08 mm⁻¹
b = 33.8005 (15) Å	T = 293 K
c = 11.3730 (5) Å	0.26 × 0.23 × 0.19 mm
β = 112.357 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	4866 reflections with I > 2σ(I)
54997 measured reflections	R_int = 0.045
8020 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
8020 reflections	Δρ_min = −0.16 e Å⁻³
453 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.7759 (2)	0.11297 (6)	0.48780 (16)	0.0696 (5)
H1	0.7122	0.0961	0.5098	0.083*
C2	0.8596 (2)	0.13996 (6)	0.57595 (16)	0.0701 (5)
H2	0.8524	0.1416	0.6551	0.084*
C3	0.9539 (3)	0.16431 (6)	0.54450 (17)	0.0816 (6)
H3	1.0143	0.1827	0.6028	0.098*
C4	0.9591 (2)	0.16147 (6)	0.42549 (16)	0.0728 (5)
H4	1.0226	0.1781	0.4023	0.087*
C5	0.86928 (18)	0.13385 (4)	0.34122 (14)	0.0497 (4)
C6	0.86531 (17)	0.13101 (4)	0.20943 (14)	0.0466 (4)
C7	0.77995 (17)	0.10220 (4)	0.12563 (14)	0.0475 (4)
H7	0.7269	0.0834	0.1525	0.057*
C8	0.77361 (16)	0.10132 (4)	0.00176 (13)	0.0449 (3)
C9	0.85548 (17)	0.13028 (4)	−0.03174 (14)	0.0495 (4)
H9	0.8538	0.1311	−0.1140	0.059*
C10	0.93975 (17)	0.15801 (4)	0.05723 (14)	0.0474 (4)
C11	1.02934 (17)	0.18938 (4)	0.02493 (14)	0.0498 (4)
C12	1.12666 (19)	0.21366 (5)	0.11818 (16)	0.0580 (4)
H12	1.1365	0.2107	0.2022	0.070*
C13	1.2091 (2)	0.24222 (5)	0.08585 (18)	0.0659 (5)
H13	1.2750	0.2589	0.1476	0.079*
C14	1.1930 (2)	0.24576 (5)	−0.03759 (18)	0.0681 (5)
H14	1.2477	0.2647	−0.0623	0.082*
C15	1.0942 (2)	0.22076 (6)	−0.12404 (18)	0.0806 (6)
H15	1.0830	0.2234	−0.2085	0.097*
C16	0.68526 (16)	0.07058 (4)	−0.08986 (13)	0.0444 (3)
C17	0.55910 (17)	0.05249 (5)	−0.07901 (14)	0.0506 (4)
H17	0.5280	0.0601	−0.0139	0.061*
C18	0.47891 (17)	0.02341 (5)	−0.16333 (14)	0.0533 (4)
H18	0.3945	0.0119	−0.1540	0.064*
C19	0.52101 (17)	0.01106 (5)	−0.26110 (14)	0.0511 (4)
C20	0.64724 (18)	0.02899 (5)	−0.27141 (14)	0.0556 (4)
H20	0.6784	0.0212	−0.3362	0.067*
C21	0.72812 (17)	0.05812 (5)	−0.18789 (14)	0.0518 (4)
H21	0.8126	0.0696	−0.1974	0.062*
C22	0.4345 (2)	−0.02102 (6)	−0.35164 (17)	0.0729 (5)
H22A	0.3543	−0.0094	−0.4231	0.109*
H22B	0.3910	−0.0389	−0.3090	0.109*
H22C	0.5030	−0.0352	−0.3806	0.109*
C23	0.5999 (2)	0.21967 (6)	−0.08254 (19)	0.0766 (6)
H23	0.5938	0.2216	−0.1659	0.092*
C24	0.6915 (2)	0.24603 (5)	0.00338 (19)	0.0700 (5)
H24	0.7459	0.2652	−0.0206	0.084*
C25	0.7009 (2)	0.24337 (5)	0.12568 (19)	0.0686 (5)
H25	0.7615	0.2609	0.1871	0.082*
C26	0.61903 (19)	0.21428 (5)	0.15698 (16)	0.0589 (4)
H26	0.6251	0.2117	0.2402	0.071*
C27	0.52811 (17)	0.18903 (4)	0.06361 (14)	0.0484 (4)
C28	0.43590 (16)	0.15754 (4)	0.09245 (14)	0.0459 (3)
C29	0.35440 (16)	0.13027 (4)	0.00119 (14)	0.0471 (4)
H29	0.3562	0.1316	−0.0799	0.057*
C30	0.26990 (16)	0.10085 (4)	0.02985 (13)	0.0439 (3)
C31	0.27262 (17)	0.10065 (4)	0.15311 (14)	0.0476 (4)
H31	0.2176	0.0817	0.1771	0.057*
C32	0.35749 (17)	0.12881 (4)	0.24004 (14)	0.0465 (4)
C33	0.36472 (18)	0.12913 (5)	0.37347 (14)	0.0510 (4)
C34	0.4341 (2)	0.15961 (5)	0.45523 (16)	0.0684 (5)
H34	0.4736	0.1812	0.4271	0.082*
C35	0.4444 (2)	0.15775 (7)	0.57910 (18)	0.0813 (6)
H35	0.4906	0.1781	0.6356	0.098*
C36	0.3861 (2)	0.12569 (7)	0.61817 (18)	0.0804 (6)
H36	0.3936	0.1234	0.7018	0.096*
C37	0.3164 (3)	0.09704 (6)	0.53035 (17)	0.0815 (6)
H37	0.2745	0.0755	0.5565	0.098*
C38	0.18624 (16)	0.07058 (4)	−0.06589 (13)	0.0430 (3)
C39	0.16367 (16)	0.03240 (4)	−0.03040 (13)	0.0478 (4)
H39	0.1968	0.0260	0.0555	0.057*
C40	0.09327 (16)	0.00391 (4)	−0.11997 (14)	0.0492 (4)
H40	0.0788	−0.0212	−0.0931	0.059*
C41	0.04346 (16)	0.01154 (4)	−0.24868 (14)	0.0481 (4)
C42	0.06321 (17)	0.04971 (5)	−0.28435 (14)	0.0520 (4)
H42	0.0287	0.0560	−0.3703	0.062*
C43	0.13286 (17)	0.07865 (5)	−0.19547 (14)	0.0508 (4)
H43	0.1443	0.1040	−0.2227	0.061*
C44	−0.0281 (2)	−0.02038 (5)	−0.34506 (16)	0.0656 (5)
H44A	−0.0878	−0.0085	−0.4254	0.098*
H44B	−0.0929	−0.0365	−0.3171	0.098*
H44C	0.0507	−0.0365	−0.3542	0.098*
N1	0.77916 (16)	0.10912 (4)	0.37216 (12)	0.0611 (4)
N2	0.94561 (14)	0.15852 (4)	0.17656 (11)	0.0497 (3)
N3	1.01214 (18)	0.19271 (4)	−0.09654 (13)	0.0711 (4)
N4	0.51837 (17)	0.19136 (4)	−0.05618 (13)	0.0663 (4)
N5	0.43839 (14)	0.15705 (4)	0.21117 (11)	0.0493 (3)
N6	0.30441 (18)	0.09797 (4)	0.40976 (13)	0.0687 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0820 (13)	0.0769 (13)	0.0565 (11)	0.0047 (10)	0.0340 (9)	0.0042 (9)
C2	0.0920 (14)	0.0748 (13)	0.0457 (9)	0.0182 (11)	0.0287 (10)	0.0024 (9)
C3	0.1102 (16)	0.0774 (14)	0.0517 (11)	−0.0114 (12)	0.0247 (11)	−0.0163 (10)
C4	0.0951 (14)	0.0686 (12)	0.0562 (11)	−0.0184 (10)	0.0304 (10)	−0.0118 (9)
C5	0.0567 (9)	0.0460 (9)	0.0464 (8)	0.0075 (7)	0.0195 (7)	0.0003 (7)
C6	0.0511 (8)	0.0433 (9)	0.0465 (8)	0.0056 (7)	0.0197 (7)	−0.0002 (7)
C7	0.0516 (9)	0.0451 (9)	0.0480 (8)	0.0020 (7)	0.0214 (7)	0.0023 (7)
C8	0.0456 (8)	0.0436 (8)	0.0460 (8)	0.0047 (7)	0.0180 (6)	0.0005 (7)
C9	0.0559 (9)	0.0502 (9)	0.0448 (8)	0.0029 (7)	0.0219 (7)	0.0006 (7)
C10	0.0494 (8)	0.0423 (8)	0.0512 (9)	0.0039 (7)	0.0199 (7)	0.0008 (7)
C11	0.0526 (9)	0.0436 (9)	0.0544 (9)	0.0054 (7)	0.0216 (7)	0.0016 (7)
C12	0.0625 (10)	0.0522 (10)	0.0599 (10)	−0.0030 (8)	0.0240 (8)	−0.0035 (8)
C13	0.0617 (11)	0.0547 (11)	0.0780 (13)	−0.0069 (8)	0.0228 (9)	−0.0062 (9)
C14	0.0708 (12)	0.0547 (11)	0.0811 (13)	−0.0083 (9)	0.0316 (10)	0.0087 (9)
C15	0.1039 (16)	0.0778 (13)	0.0638 (12)	−0.0254 (12)	0.0358 (11)	0.0056 (10)
C16	0.0449 (8)	0.0472 (9)	0.0409 (8)	0.0046 (6)	0.0161 (6)	0.0005 (6)
C17	0.0482 (9)	0.0587 (10)	0.0498 (9)	0.0031 (7)	0.0241 (7)	−0.0033 (7)
C18	0.0432 (8)	0.0615 (10)	0.0563 (9)	−0.0028 (7)	0.0201 (7)	−0.0021 (8)
C19	0.0475 (9)	0.0551 (10)	0.0451 (8)	0.0005 (7)	0.0113 (7)	−0.0018 (7)
C20	0.0586 (10)	0.0670 (11)	0.0457 (8)	−0.0008 (8)	0.0248 (7)	−0.0073 (8)
C21	0.0502 (9)	0.0605 (10)	0.0486 (9)	−0.0054 (7)	0.0230 (7)	−0.0038 (7)
C22	0.0701 (12)	0.0765 (13)	0.0655 (11)	−0.0142 (10)	0.0185 (9)	−0.0156 (10)
C23	0.1024 (15)	0.0667 (12)	0.0709 (12)	−0.0243 (11)	0.0446 (11)	−0.0012 (10)
C24	0.0744 (12)	0.0543 (11)	0.0869 (14)	−0.0122 (9)	0.0372 (11)	0.0025 (10)
C25	0.0680 (11)	0.0541 (11)	0.0800 (13)	−0.0127 (9)	0.0241 (10)	−0.0101 (9)
C26	0.0625 (10)	0.0535 (10)	0.0614 (10)	−0.0034 (8)	0.0243 (8)	−0.0040 (8)
C27	0.0513 (9)	0.0410 (8)	0.0553 (9)	0.0044 (7)	0.0229 (7)	0.0002 (7)
C28	0.0486 (8)	0.0414 (8)	0.0503 (9)	0.0058 (7)	0.0219 (7)	0.0017 (7)
C29	0.0530 (9)	0.0468 (9)	0.0450 (8)	0.0027 (7)	0.0224 (7)	0.0017 (7)
C30	0.0435 (8)	0.0435 (8)	0.0461 (8)	0.0048 (6)	0.0186 (6)	0.0025 (6)
C31	0.0502 (8)	0.0460 (9)	0.0485 (8)	0.0000 (7)	0.0210 (7)	0.0029 (7)
C32	0.0502 (8)	0.0442 (9)	0.0468 (8)	0.0066 (7)	0.0203 (7)	0.0025 (7)
C33	0.0553 (9)	0.0515 (9)	0.0479 (9)	0.0054 (7)	0.0215 (7)	0.0007 (7)
C34	0.0871 (13)	0.0642 (11)	0.0596 (11)	−0.0078 (10)	0.0344 (10)	−0.0104 (9)
C35	0.0947 (15)	0.0931 (16)	0.0575 (12)	−0.0080 (12)	0.0306 (11)	−0.0209 (11)
C36	0.0967 (15)	0.1012 (16)	0.0484 (10)	0.0077 (13)	0.0333 (10)	0.0013 (11)
C37	0.1110 (16)	0.0863 (14)	0.0567 (11)	−0.0095 (12)	0.0426 (11)	0.0037 (10)
C38	0.0425 (8)	0.0447 (8)	0.0437 (8)	0.0025 (6)	0.0185 (6)	0.0026 (6)
C39	0.0498 (8)	0.0505 (9)	0.0428 (8)	0.0032 (7)	0.0175 (7)	0.0064 (7)
C40	0.0501 (9)	0.0441 (8)	0.0538 (9)	−0.0015 (7)	0.0203 (7)	0.0030 (7)
C41	0.0435 (8)	0.0521 (9)	0.0492 (9)	0.0016 (7)	0.0180 (7)	−0.0018 (7)
C42	0.0540 (9)	0.0598 (10)	0.0410 (8)	−0.0002 (7)	0.0167 (7)	0.0033 (7)
C43	0.0544 (9)	0.0498 (9)	0.0488 (9)	−0.0014 (7)	0.0202 (7)	0.0077 (7)
C44	0.0693 (11)	0.0649 (11)	0.0597 (10)	−0.0053 (9)	0.0214 (9)	−0.0093 (8)
N1	0.0718 (9)	0.0650 (9)	0.0507 (8)	−0.0017 (7)	0.0281 (7)	−0.0004 (7)
N2	0.0554 (8)	0.0458 (7)	0.0493 (7)	0.0023 (6)	0.0212 (6)	−0.0017 (6)
N3	0.0888 (11)	0.0702 (10)	0.0556 (9)	−0.0222 (8)	0.0291 (8)	0.0002 (7)
N4	0.0849 (10)	0.0605 (9)	0.0617 (9)	−0.0195 (8)	0.0370 (8)	−0.0042 (7)
N5	0.0535 (7)	0.0459 (7)	0.0499 (7)	0.0034 (6)	0.0212 (6)	−0.0001 (6)
N6	0.0913 (11)	0.0678 (10)	0.0528 (8)	−0.0086 (8)	0.0340 (8)	0.0002 (7)

Geometric parameters (Å, º) top

C1—N1	1.334 (2)	C23—N4	1.333 (2)
C1—C2	1.364 (3)	C23—C24	1.362 (2)
C1—H1	0.9300	C23—H23	0.9300
C2—C3	1.358 (3)	C24—C25	1.363 (2)
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.376 (2)	C25—C26	1.379 (2)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.376 (2)	C26—C27	1.379 (2)
C4—H4	0.9300	C26—H26	0.9300
C5—N1	1.333 (2)	C27—N4	1.3324 (19)
C5—C6	1.488 (2)	C27—C28	1.489 (2)
C6—N2	1.3407 (18)	C28—N5	1.3415 (18)
C6—C7	1.387 (2)	C28—C29	1.383 (2)
C7—C8	1.3875 (19)	C29—C30	1.3898 (19)
C7—H7	0.9300	C29—H29	0.9300
C8—C9	1.388 (2)	C30—C31	1.3923 (19)
C8—C16	1.4835 (19)	C30—C38	1.484 (2)
C9—C10	1.387 (2)	C31—C32	1.387 (2)
C9—H9	0.9300	C31—H31	0.9300
C10—N2	1.3371 (18)	C32—N5	1.3399 (18)
C10—C11	1.488 (2)	C32—C33	1.493 (2)
C11—N3	1.3329 (19)	C33—N6	1.336 (2)
C11—C12	1.379 (2)	C33—C34	1.376 (2)
C12—C13	1.376 (2)	C34—C35	1.376 (2)
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.358 (2)	C35—C36	1.364 (3)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.362 (2)	C36—C37	1.367 (3)
C14—H14	0.9300	C36—H36	0.9300
C15—N3	1.335 (2)	C37—N6	1.333 (2)
C15—H15	0.9300	C37—H37	0.9300
C16—C17	1.387 (2)	C38—C43	1.3910 (19)
C16—C21	1.389 (2)	C38—C39	1.3925 (19)
C17—C18	1.381 (2)	C39—C40	1.376 (2)
C17—H17	0.9300	C39—H39	0.9300
C18—C19	1.381 (2)	C40—C41	1.381 (2)
C18—H18	0.9300	C40—H40	0.9300
C19—C20	1.383 (2)	C41—C42	1.386 (2)
C19—C22	1.505 (2)	C41—C44	1.503 (2)
C20—C21	1.380 (2)	C42—C43	1.381 (2)
C20—H20	0.9300	C42—H42	0.9300
C21—H21	0.9300	C43—H43	0.9300
C22—H22A	0.9600	C44—H44A	0.9600
C22—H22B	0.9600	C44—H44B	0.9600
C22—H22C	0.9600	C44—H44C	0.9600

N1—C1—C2	124.41 (18)	C23—C24—C25	117.76 (17)
N1—C1—H1	117.8	C23—C24—H24	121.1
C2—C1—H1	117.8	C25—C24—H24	121.1
C3—C2—C1	117.89 (17)	C24—C25—C26	119.05 (17)
C3—C2—H2	121.1	C24—C25—H25	120.5
C1—C2—H2	121.1	C26—C25—H25	120.5
C2—C3—C4	119.31 (18)	C27—C26—C25	119.30 (16)
C2—C3—H3	120.3	C27—C26—H26	120.4
C4—C3—H3	120.3	C25—C26—H26	120.4
C5—C4—C3	119.28 (18)	N4—C27—C26	122.10 (15)
C5—C4—H4	120.4	N4—C27—C28	116.66 (13)
C3—C4—H4	120.4	C26—C27—C28	121.24 (14)
N1—C5—C4	121.93 (15)	N5—C28—C29	122.58 (14)
N1—C5—C6	116.85 (14)	N5—C28—C27	116.29 (13)
C4—C5—C6	121.20 (15)	C29—C28—C27	121.13 (13)
N2—C6—C7	122.61 (14)	C28—C29—C30	120.46 (14)
N2—C6—C5	115.86 (13)	C28—C29—H29	119.8
C7—C6—C5	121.51 (14)	C30—C29—H29	119.8
C6—C7—C8	120.12 (14)	C29—C30—C31	116.59 (13)
C6—C7—H7	119.9	C29—C30—C38	120.98 (13)
C8—C7—H7	119.9	C31—C30—C38	122.40 (13)
C7—C8—C9	116.77 (13)	C32—C31—C30	119.89 (14)
C7—C8—C16	121.56 (13)	C32—C31—H31	120.1
C9—C8—C16	121.67 (13)	C30—C31—H31	120.1
C10—C9—C8	120.12 (14)	N5—C32—C31	122.94 (14)
C10—C9—H9	119.9	N5—C32—C33	115.74 (13)
C8—C9—H9	119.9	C31—C32—C33	121.32 (14)
N2—C10—C9	122.67 (14)	N6—C33—C34	122.12 (15)
N2—C10—C11	115.70 (13)	N6—C33—C32	116.66 (14)
C9—C10—C11	121.63 (14)	C34—C33—C32	121.20 (15)
N3—C11—C12	121.97 (15)	C33—C34—C35	119.17 (18)
N3—C11—C10	117.35 (14)	C33—C34—H34	120.4
C12—C11—C10	120.68 (14)	C35—C34—H34	120.4
C13—C12—C11	119.48 (16)	C36—C35—C34	119.33 (18)
C13—C12—H12	120.3	C36—C35—H35	120.3
C11—C12—H12	120.3	C34—C35—H35	120.3
C14—C13—C12	119.06 (17)	C35—C36—C37	117.83 (18)
C14—C13—H13	120.5	C35—C36—H36	121.1
C12—C13—H13	120.5	C37—C36—H36	121.1
C13—C14—C15	117.88 (17)	N6—C37—C36	124.31 (19)
C13—C14—H14	121.1	N6—C37—H37	117.8
C15—C14—H14	121.1	C36—C37—H37	117.8
N3—C15—C14	124.88 (18)	C43—C38—C39	117.06 (13)
N3—C15—H15	117.6	C43—C38—C30	121.29 (13)
C14—C15—H15	117.6	C39—C38—C30	121.59 (13)
C17—C16—C21	117.46 (14)	C40—C39—C38	121.22 (13)
C17—C16—C8	121.33 (13)	C40—C39—H39	119.4
C21—C16—C8	121.19 (13)	C38—C39—H39	119.4
C18—C17—C16	121.04 (14)	C39—C40—C41	121.90 (14)
C18—C17—H17	119.5	C39—C40—H40	119.1
C16—C17—H17	119.5	C41—C40—H40	119.1
C19—C18—C17	121.60 (14)	C40—C41—C42	117.02 (14)
C19—C18—H18	119.2	C40—C41—C44	121.10 (14)
C17—C18—H18	119.2	C42—C41—C44	121.88 (14)
C18—C19—C20	117.29 (14)	C43—C42—C41	121.67 (14)
C18—C19—C22	121.39 (15)	C43—C42—H42	119.2
C20—C19—C22	121.32 (15)	C41—C42—H42	119.2
C21—C20—C19	121.65 (14)	C42—C43—C38	121.10 (14)
C21—C20—H20	119.2	C42—C43—H43	119.4
C19—C20—H20	119.2	C38—C43—H43	119.4
C20—C21—C16	120.96 (14)	C41—C44—H44A	109.5
C20—C21—H21	119.5	C41—C44—H44B	109.5
C16—C21—H21	119.5	H44A—C44—H44B	109.5
C19—C22—H22A	109.5	C41—C44—H44C	109.5
C19—C22—H22B	109.5	H44A—C44—H44C	109.5
H22A—C22—H22B	109.5	H44B—C44—H44C	109.5
C19—C22—H22C	109.5	C5—N1—C1	117.14 (15)
H22A—C22—H22C	109.5	C10—N2—C6	117.70 (13)
H22B—C22—H22C	109.5	C11—N3—C15	116.73 (15)
N4—C23—C24	124.95 (18)	C27—N4—C23	116.84 (15)
N4—C23—H23	117.5	C32—N5—C28	117.55 (13)
C24—C23—H23	117.5	C37—N6—C33	117.22 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1	0.93	2.82	3.5303 (1)	134 (2)
C21—H21···Cg1ⁱ	0.93	2.87	3.5767 (1)	133 (2)
C39—H39···Cg2ⁱⁱ	0.93	2.93	3.5398 (1)	125 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃
M_r	323.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.4575 (4), 33.8005 (15), 11.3730 (5)
β (°)	112.357 (3)
V (Å³)	3362.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.23 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	54997, 8020, 4866
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.03
No. of reflections	8020
No. of parameters	453
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTLXP (Bruker, 2004).