Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060904/kj2073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060904/kj2073Isup2.hkl |
CCDC reference: 673065
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
checkCIF/PLATON results
No syntax errors found
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
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.
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.
Carbon-bound H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).
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).
C22H17N3 | F(000) = 1360 |
Mr = 323.39 | Dx = 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 |
Bruker APEXII area-detector diffractometer | 4866 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 27.9°, θmin = 2.0° |
ϕ and ω scan | h = −12→12 |
54997 measured reflections | k = −44→43 |
8020 independent reflections | l = −14→14 |
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(Fo2) + (0.0511P)2 + 0.4806P] where P = (Fo2 + 2Fc2)/3 |
8020 reflections | (Δ/σ)max < 0.001 |
453 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C22H17N3 | V = 3362.3 (3) Å3 |
Mr = 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)° |
Bruker APEXII area-detector diffractometer | 4866 reflections with I > 2σ(I) |
54997 measured reflections | Rint = 0.045 |
8020 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
8020 reflections | Δρmin = −0.16 e Å−3 |
453 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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. |
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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).