organic compounds
In the title compound, C15H10ClN3, the terpyridine unit adopts a trans,trans conformation. Molecules assemble into π-stacked columns along the b axis, with an interplanar distance of 3.51 Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019180/cf2025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019180/cf2025Isup2.hkl |
CCDC reference: 610729
Computing details top
Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.
4'-Chloro-2,2':6',2''-terpyridine top
Crystal data top
C15H10ClN3 | F(000) = 552 |
Mr = 267.72 | Dx = 1.460 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3476 reflections |
a = 29.8317 (15) Å | θ = 1–27° |
b = 3.8344 (2) Å | µ = 0.30 mm−1 |
c = 10.6476 (5) Å | T = 173 K |
V = 1217.94 (11) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.17 × 0.04 mm |
Data collection top
Nonius KappaCCD diffractometer | 1848 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.098 |
φ and ω scans | θmax = 27.6°, θmin = 1.4° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −38→38 |
Tmin = 0.95, Tmax = 0.99 | k = −4→4 |
7250 measured reflections | l = −13→12 |
2554 independent reflections |
Refinement top
Refinement on F | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(F2) + (0.02P)2] where P = [max(Fo2,0) + 2Fc2]/3 |
wR(F2) = 0.032 | (Δ/σ)max = 0.001 |
S = 0.94 | Δρmax = 0.14 e Å−3 |
1848 reflections | Δρmin = −0.18 e Å−3 |
173 parameters | Absolute structure: Flack (1983), 1130 Friedel pairs |
1 restraint | Absolute structure parameter: −0.04 (6) |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.839243 (18) | 0.64167 (15) | 1.05641 (7) | 0.0391 | |
N1 | 0.99400 (6) | 1.1265 (5) | 0.89573 (16) | 0.0304 | |
N2 | 0.89799 (5) | 1.0349 (4) | 0.69348 (16) | 0.0276 | |
N3 | 0.78951 (6) | 0.7575 (5) | 0.58118 (17) | 0.0350 | |
C1 | 1.03672 (8) | 1.2342 (7) | 0.8905 (2) | 0.0345 | |
C2 | 1.05556 (8) | 1.3886 (6) | 0.7862 (2) | 0.0342 | |
C3 | 1.02932 (8) | 1.4367 (6) | 0.6809 (2) | 0.0332 | |
C4 | 0.98525 (7) | 1.3210 (6) | 0.68374 (19) | 0.0304 | |
C5 | 0.96894 (7) | 1.1684 (5) | 0.79145 (19) | 0.0263 | |
C6 | 0.92195 (7) | 1.0365 (5) | 0.8001 (2) | 0.0262 | |
C7 | 0.90514 (7) | 0.9187 (6) | 0.9141 (2) | 0.0281 | |
C8 | 0.86177 (7) | 0.7951 (6) | 0.9158 (2) | 0.0298 | |
C9 | 0.83628 (7) | 0.7896 (6) | 0.8088 (2) | 0.0299 | |
C10 | 0.85575 (7) | 0.9135 (5) | 0.6982 (2) | 0.0275 | |
C11 | 0.83026 (6) | 0.9081 (5) | 0.5776 (2) | 0.0277 | |
C12 | 0.84819 (7) | 1.0452 (6) | 0.4684 (2) | 0.0319 | |
C13 | 0.82400 (8) | 1.0238 (6) | 0.3580 (2) | 0.0366 | |
C14 | 0.78250 (8) | 0.8660 (6) | 0.3603 (2) | 0.0375 | |
C15 | 0.76683 (8) | 0.7425 (7) | 0.4730 (2) | 0.0386 | |
H11 | 1.0552 | 1.2019 | 0.9634 | 0.0414* | |
H21 | 1.0864 | 1.4613 | 0.7868 | 0.0411* | |
H31 | 1.0413 | 1.5476 | 0.6073 | 0.0398* | |
H41 | 0.9663 | 1.3470 | 0.6114 | 0.0365* | |
H71 | 0.9231 | 0.9232 | 0.9890 | 0.0337* | |
H91 | 0.8061 | 0.7035 | 0.8098 | 0.0359* | |
H121 | 0.8771 | 1.1543 | 0.4693 | 0.0383* | |
H131 | 0.8359 | 1.1169 | 0.2812 | 0.0439* | |
H141 | 0.7650 | 0.8431 | 0.2850 | 0.0450* | |
H151 | 0.7376 | 0.6381 | 0.4743 | 0.0463* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0444 (3) | 0.0431 (3) | 0.0299 (3) | −0.0051 (3) | 0.0070 (3) | 0.0049 (3) |
N1 | 0.0289 (9) | 0.0335 (11) | 0.0287 (10) | 0.0029 (9) | −0.0015 (8) | −0.0028 (9) |
N2 | 0.0283 (9) | 0.0278 (10) | 0.0267 (10) | 0.0018 (8) | 0.0005 (8) | −0.0011 (8) |
N3 | 0.0287 (9) | 0.0368 (11) | 0.0396 (14) | 0.0001 (8) | 0.0004 (8) | −0.0052 (9) |
C1 | 0.0286 (11) | 0.0385 (14) | 0.0363 (15) | 0.0045 (11) | −0.0042 (10) | −0.0081 (12) |
C2 | 0.0286 (11) | 0.0350 (14) | 0.0390 (14) | −0.0024 (10) | 0.0019 (10) | −0.0047 (11) |
C3 | 0.0366 (12) | 0.0287 (13) | 0.0344 (14) | −0.0008 (10) | 0.0082 (10) | −0.0013 (11) |
C4 | 0.0333 (12) | 0.0305 (13) | 0.0274 (13) | 0.0005 (10) | −0.0014 (10) | −0.0014 (11) |
C5 | 0.0276 (11) | 0.0243 (11) | 0.0270 (12) | 0.0024 (10) | 0.0012 (9) | −0.0044 (10) |
C6 | 0.0300 (11) | 0.0225 (11) | 0.0260 (11) | 0.0043 (9) | −0.0017 (9) | −0.0015 (10) |
C7 | 0.0338 (11) | 0.0251 (12) | 0.0254 (12) | 0.0021 (9) | 0.0001 (10) | 0.0006 (10) |
C8 | 0.0338 (11) | 0.0304 (13) | 0.0252 (12) | 0.0016 (11) | 0.0050 (10) | 0.0031 (10) |
C9 | 0.0323 (12) | 0.0258 (12) | 0.0316 (13) | −0.0003 (10) | 0.0053 (10) | −0.0017 (10) |
C10 | 0.0270 (11) | 0.0263 (12) | 0.0292 (13) | 0.0035 (9) | 0.0010 (10) | −0.0030 (10) |
C11 | 0.0268 (10) | 0.0265 (12) | 0.0297 (15) | 0.0027 (8) | 0.0014 (9) | −0.0022 (10) |
C12 | 0.0303 (11) | 0.0338 (15) | 0.0315 (13) | 0.0038 (10) | 0.0008 (10) | 0.0000 (11) |
C13 | 0.0406 (13) | 0.0371 (14) | 0.0320 (14) | 0.0060 (12) | −0.0016 (11) | 0.0000 (12) |
C14 | 0.0352 (12) | 0.0431 (15) | 0.0343 (14) | 0.0094 (12) | −0.0089 (11) | −0.0052 (12) |
C15 | 0.0319 (12) | 0.0427 (15) | 0.0411 (14) | 0.0011 (11) | −0.0018 (11) | −0.0065 (13) |
Geometric parameters (Å, º) top
Cl1—C8 | 1.743 (2) | C6—C7 | 1.389 (3) |
N1—C1 | 1.341 (3) | C7—C8 | 1.378 (3) |
N1—C5 | 1.348 (3) | C7—H71 | 0.960 |
N2—C6 | 1.341 (3) | C8—C9 | 1.370 (3) |
N2—C10 | 1.344 (3) | C9—C10 | 1.396 (3) |
N3—C11 | 1.346 (3) | C9—H91 | 0.960 |
N3—C15 | 1.337 (3) | C10—C11 | 1.493 (3) |
C1—C2 | 1.378 (3) | C11—C12 | 1.384 (3) |
C1—H11 | 0.960 | C12—C13 | 1.382 (3) |
C2—C3 | 1.380 (3) | C12—H121 | 0.960 |
C2—H21 | 0.960 | C13—C14 | 1.378 (3) |
C3—C4 | 1.388 (3) | C13—H131 | 0.960 |
C3—H31 | 0.960 | C14—C15 | 1.373 (3) |
C4—C5 | 1.376 (3) | C14—H141 | 0.960 |
C4—H41 | 0.960 | C15—H151 | 0.960 |
C5—C6 | 1.493 (3) | ||
C1—N1—C5 | 117.12 (18) | Cl1—C8—C7 | 119.28 (18) |
C6—N2—C10 | 118.00 (18) | Cl1—C8—C9 | 119.69 (16) |
C11—N3—C15 | 116.8 (2) | C7—C8—C9 | 121.0 (2) |
N1—C1—C2 | 123.6 (2) | C8—C9—C10 | 117.7 (2) |
N1—C1—H11 | 118.2 | C8—C9—H91 | 121.1 |
C2—C1—H11 | 118.2 | C10—C9—H91 | 121.1 |
C1—C2—C3 | 118.7 (2) | C9—C10—N2 | 122.6 (2) |
C1—C2—H21 | 120.6 | C9—C10—C11 | 120.59 (18) |
C3—C2—H21 | 120.6 | N2—C10—C11 | 116.74 (19) |
C2—C3—C4 | 118.5 (2) | C10—C11—N3 | 116.20 (19) |
C2—C3—H31 | 120.8 | C10—C11—C12 | 121.39 (18) |
C4—C3—H31 | 120.8 | N3—C11—C12 | 122.4 (2) |
C3—C4—C5 | 119.3 (2) | C11—C12—C13 | 119.4 (2) |
C3—C4—H41 | 120.4 | C11—C12—H121 | 120.3 |
C5—C4—H41 | 120.4 | C13—C12—H121 | 120.3 |
C4—C5—N1 | 122.76 (18) | C12—C13—C14 | 118.7 (2) |
C4—C5—C6 | 121.81 (19) | C12—C13—H131 | 120.7 |
N1—C5—C6 | 115.43 (18) | C14—C13—H131 | 120.7 |
C5—C6—N2 | 116.74 (18) | C13—C14—C15 | 118.2 (2) |
C5—C6—C7 | 120.18 (19) | C13—C14—H141 | 120.9 |
N2—C6—C7 | 123.08 (19) | C15—C14—H141 | 120.9 |
C6—C7—C8 | 117.5 (2) | C14—C15—N3 | 124.5 (2) |
C6—C7—H71 | 121.2 | C14—C15—H151 | 117.8 |
C8—C7—H71 | 121.2 | N3—C15—H151 | 117.8 |