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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019180/cf2025sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019180/cf2025Isup2.hkl
Contains datablock I

CCDC reference: 610729

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.032
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.55 From the CIF: _reflns_number_total 2554 Count of symmetry unique reflns 1467 Completeness (_total/calc) 174.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1087 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

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
C15H10ClN3F(000) = 552
Mr = 267.72Dx = 1.460 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3476 reflections
a = 29.8317 (15) Åθ = 1–27°
b = 3.8344 (2) ŵ = 0.30 mm1
c = 10.6476 (5) ÅT = 173 K
V = 1217.94 (11) Å3Plate, colourless
Z = 40.20 × 0.17 × 0.04 mm
Data collection top
Nonius KappaCCD
diffractometer
1848 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.098
φ and ω scansθmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 3838
Tmin = 0.95, Tmax = 0.99k = 44
7250 measured reflectionsl = 1312
2554 independent reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 0.94Δρmax = 0.14 e Å3
1848 reflectionsΔρmin = 0.18 e Å3
173 parametersAbsolute structure: Flack (1983), 1130 Friedel pairs
1 restraintAbsolute 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
xyzUiso*/Ueq
Cl10.839243 (18)0.64167 (15)1.05641 (7)0.0391
N10.99400 (6)1.1265 (5)0.89573 (16)0.0304
N20.89799 (5)1.0349 (4)0.69348 (16)0.0276
N30.78951 (6)0.7575 (5)0.58118 (17)0.0350
C11.03672 (8)1.2342 (7)0.8905 (2)0.0345
C21.05556 (8)1.3886 (6)0.7862 (2)0.0342
C31.02932 (8)1.4367 (6)0.6809 (2)0.0332
C40.98525 (7)1.3210 (6)0.68374 (19)0.0304
C50.96894 (7)1.1684 (5)0.79145 (19)0.0263
C60.92195 (7)1.0365 (5)0.8001 (2)0.0262
C70.90514 (7)0.9187 (6)0.9141 (2)0.0281
C80.86177 (7)0.7951 (6)0.9158 (2)0.0298
C90.83628 (7)0.7896 (6)0.8088 (2)0.0299
C100.85575 (7)0.9135 (5)0.6982 (2)0.0275
C110.83026 (6)0.9081 (5)0.5776 (2)0.0277
C120.84819 (7)1.0452 (6)0.4684 (2)0.0319
C130.82400 (8)1.0238 (6)0.3580 (2)0.0366
C140.78250 (8)0.8660 (6)0.3603 (2)0.0375
C150.76683 (8)0.7425 (7)0.4730 (2)0.0386
H111.05521.20190.96340.0414*
H211.08641.46130.78680.0411*
H311.04131.54760.60730.0398*
H410.96631.34700.61140.0365*
H710.92310.92320.98900.0337*
H910.80610.70350.80980.0359*
H1210.87711.15430.46930.0383*
H1310.83591.11690.28120.0439*
H1410.76500.84310.28500.0450*
H1510.73760.63810.47430.0463*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0444 (3)0.0431 (3)0.0299 (3)0.0051 (3)0.0070 (3)0.0049 (3)
N10.0289 (9)0.0335 (11)0.0287 (10)0.0029 (9)0.0015 (8)0.0028 (9)
N20.0283 (9)0.0278 (10)0.0267 (10)0.0018 (8)0.0005 (8)0.0011 (8)
N30.0287 (9)0.0368 (11)0.0396 (14)0.0001 (8)0.0004 (8)0.0052 (9)
C10.0286 (11)0.0385 (14)0.0363 (15)0.0045 (11)0.0042 (10)0.0081 (12)
C20.0286 (11)0.0350 (14)0.0390 (14)0.0024 (10)0.0019 (10)0.0047 (11)
C30.0366 (12)0.0287 (13)0.0344 (14)0.0008 (10)0.0082 (10)0.0013 (11)
C40.0333 (12)0.0305 (13)0.0274 (13)0.0005 (10)0.0014 (10)0.0014 (11)
C50.0276 (11)0.0243 (11)0.0270 (12)0.0024 (10)0.0012 (9)0.0044 (10)
C60.0300 (11)0.0225 (11)0.0260 (11)0.0043 (9)0.0017 (9)0.0015 (10)
C70.0338 (11)0.0251 (12)0.0254 (12)0.0021 (9)0.0001 (10)0.0006 (10)
C80.0338 (11)0.0304 (13)0.0252 (12)0.0016 (11)0.0050 (10)0.0031 (10)
C90.0323 (12)0.0258 (12)0.0316 (13)0.0003 (10)0.0053 (10)0.0017 (10)
C100.0270 (11)0.0263 (12)0.0292 (13)0.0035 (9)0.0010 (10)0.0030 (10)
C110.0268 (10)0.0265 (12)0.0297 (15)0.0027 (8)0.0014 (9)0.0022 (10)
C120.0303 (11)0.0338 (15)0.0315 (13)0.0038 (10)0.0008 (10)0.0000 (11)
C130.0406 (13)0.0371 (14)0.0320 (14)0.0060 (12)0.0016 (11)0.0000 (12)
C140.0352 (12)0.0431 (15)0.0343 (14)0.0094 (12)0.0089 (11)0.0052 (12)
C150.0319 (12)0.0427 (15)0.0411 (14)0.0011 (11)0.0018 (11)0.0065 (13)
Geometric parameters (Å, º) top
Cl1—C81.743 (2)C6—C71.389 (3)
N1—C11.341 (3)C7—C81.378 (3)
N1—C51.348 (3)C7—H710.960
N2—C61.341 (3)C8—C91.370 (3)
N2—C101.344 (3)C9—C101.396 (3)
N3—C111.346 (3)C9—H910.960
N3—C151.337 (3)C10—C111.493 (3)
C1—C21.378 (3)C11—C121.384 (3)
C1—H110.960C12—C131.382 (3)
C2—C31.380 (3)C12—H1210.960
C2—H210.960C13—C141.378 (3)
C3—C41.388 (3)C13—H1310.960
C3—H310.960C14—C151.373 (3)
C4—C51.376 (3)C14—H1410.960
C4—H410.960C15—H1510.960
C5—C61.493 (3)
C1—N1—C5117.12 (18)Cl1—C8—C7119.28 (18)
C6—N2—C10118.00 (18)Cl1—C8—C9119.69 (16)
C11—N3—C15116.8 (2)C7—C8—C9121.0 (2)
N1—C1—C2123.6 (2)C8—C9—C10117.7 (2)
N1—C1—H11118.2C8—C9—H91121.1
C2—C1—H11118.2C10—C9—H91121.1
C1—C2—C3118.7 (2)C9—C10—N2122.6 (2)
C1—C2—H21120.6C9—C10—C11120.59 (18)
C3—C2—H21120.6N2—C10—C11116.74 (19)
C2—C3—C4118.5 (2)C10—C11—N3116.20 (19)
C2—C3—H31120.8C10—C11—C12121.39 (18)
C4—C3—H31120.8N3—C11—C12122.4 (2)
C3—C4—C5119.3 (2)C11—C12—C13119.4 (2)
C3—C4—H41120.4C11—C12—H121120.3
C5—C4—H41120.4C13—C12—H121120.3
C4—C5—N1122.76 (18)C12—C13—C14118.7 (2)
C4—C5—C6121.81 (19)C12—C13—H131120.7
N1—C5—C6115.43 (18)C14—C13—H131120.7
C5—C6—N2116.74 (18)C13—C14—C15118.2 (2)
C5—C6—C7120.18 (19)C13—C14—H141120.9
N2—C6—C7123.08 (19)C15—C14—H141120.9
C6—C7—C8117.5 (2)C14—C15—N3124.5 (2)
C6—C7—H71121.2C14—C15—H151117.8
C8—C7—H71121.2N3—C15—H151117.8
 

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