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The crystal structure of 2,6-lutidine (2,6-di­methyl­pyridine, C7H9N), has been determined at 120 (2) K following in situ crystal growth from the liquid. In the non-centrosymmetric space group Fdd2, the asymmetric unit comprises half a mol­ecule, each mol­ecule being sited on a crystallographic diad axis. Molecules are linked via linear C—H...N interactions into one-dimensional chains that align in a parallel manner, giving rise to macroscopically polar crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019869/na6108sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019869/na6108Isup2.hkl
Contains datablock I

CCDC reference: 177234

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.140
  • Data-to-parameter ratio = 8.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.39 From the CIF: _reflns_number_total 387 Count of symmetry unique reflns 399 Completeness (_total/calc) 96.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no 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.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick,1997); software used to prepare material for publication: SHELXL97.

2,6-Dimethylpyridine top
Crystal data top
C7H9NDx = 1.104 Mg m3
Mr = 107.15Melting point: 267 K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
a = 13.782 (3) ÅCell parameters from 1553 reflections
b = 14.805 (3) Åθ = 1.0–27.5°
c = 6.317 (1) ŵ = 0.07 mm1
V = 1288.9 (4) Å3T = 120 K
Z = 8Cylinder, colourless
F(000) = 4640.15 mm (radius)
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.034
Radiation source: fine-focus sealed tubeθmax = 27.4°, θmin = 3.8°
Thin–slice ω and φ scansh = 1713
1429 measured reflectionsk = 1915
387 independent reflectionsl = 78
351 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0788P)2 + 0.8716P]
where P = (Fo2 + 2Fc2)/3
387 reflections(Δ/σ)max = 0.007
46 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.18 e Å3
Special details top

Experimental. Crystal grown in situ in a 0.3 mm Lindemann tube at 260 K. Absolute structure could not be determined and Friedel pairs (288) were averaged for the refinement.

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
xyzUiso*/Ueq
N10.00000.50000.0817 (4)0.0299 (8)
C20.0155 (2)0.57658 (18)0.1892 (3)0.0325 (8)
C30.0153 (2)0.5788 (2)0.4104 (4)0.0359 (8)
H30.030 (3)0.637 (2)0.483 (6)0.050 (11)*
C40.00000.50000.5226 (7)0.0385 (11)
H40.00000.50000.665 (8)0.026 (11)*
C70.0315 (2)0.66065 (19)0.0612 (6)0.0459 (8)
H7A0.06580.64530.06980.078 (7)*
H7B0.07040.70360.14320.078 (7)*
H7C0.03130.68800.02650.078 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0301 (14)0.0398 (18)0.0198 (19)0.0056 (13)0.0000.000
C20.0310 (17)0.038 (2)0.0286 (19)0.0029 (11)0.0009 (11)0.0026 (11)
C30.0373 (19)0.042 (2)0.0280 (15)0.0042 (11)0.0016 (12)0.0053 (12)
C40.039 (2)0.053 (3)0.024 (2)0.0097 (17)0.0000.000
C70.0536 (16)0.0422 (16)0.0420 (18)0.0118 (12)0.0056 (17)0.0076 (16)
Geometric parameters (Å, º) top
N1—C21.339 (3)C4—C3i1.381 (4)
N1—C2i1.339 (3)C4—H40.90 (5)
C2—C31.397 (3)C7—H7A0.9800
C2—C71.500 (4)C7—H7B0.9800
C3—C41.381 (4)C7—H7C0.9800
C3—H31.00 (4)
C2—N1—C2i119.0 (3)C3i—C4—H4120.9 (2)
N1—C2—C3121.8 (3)C3—C4—H4120.9 (2)
N1—C2—C7116.90 (19)C2—C7—H7A109.5
C3—C2—C7121.3 (3)C2—C7—H7B109.5
C4—C3—C2119.6 (3)H7A—C7—H7B109.5
C4—C3—H3122 (2)C2—C7—H7C109.5
C2—C3—H3118 (2)H7A—C7—H7C109.5
C3i—C4—C3118.2 (4)H7B—C7—H7C109.5
C2i—N1—C2—C30.5 (3)C7—C2—C3—C4179.8 (2)
C2i—N1—C2—C7179.4 (3)C2—C3—C4—C3i0.4 (2)
N1—C2—C3—C40.9 (5)
Symmetry code: (i) x, y+1, z.
 

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