6,6′-Bis­(chloro­methyl)-2,2′-bi­pyridine

Lindoy, L.F.; McMurtrie, J.C.; Price, J.R.

doi:10.1107/S1600536804008852

6,6'-Bis(chloromethyl)-2,2'-bipyridine

L. F. Lindoy, J. C. McMurtrie and J. R. Price

In the crystalline state, the two pyridyl groups of the centrosymmetric title molecule, C₁₂H₁₀Cl₂N₂, are coplanar, with the N atoms trans to each other and with the Cl atoms of the chloromethyl groups protruding on opposite sides of the bipyridyl plane. In the crystal structure, the molecules are arranged in discrete layers propagated by edge-to-face and offset face-to-face aryl-aryl interactions. The interlayer spaces are occupied by chloromethyl groups.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008852/tk6161sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008852/tk6161Isup2.hkl Contains datablock I

CCDC reference: 239292

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.025
wR factor = 0.069
Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.11

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer (Allen et al., 2004).

6,6'-Bis(chloromethyl)-2,2'-bipyridine top

Crystal data top

C₁₂H₁₀Cl₂N₂	F(000) = 260
M_r = 253.12	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 430 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.7692 (11) Å	Cell parameters from 4044 reflections
b = 4.3678 (4) Å	θ = 2.5–28.4°
c = 10.8889 (10) Å	µ = 0.55 mm⁻¹
β = 93.588 (1)°	T = 150 K
V = 558.65 (9) Å³	Prism, colourless
Z = 2	0.54 × 0.40 × 0.30 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	1337 independent reflections
Radiation source: sealed tube	1269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −15→15
T_min = 0.755, T_max = 0.850	k = −5→5
5097 measured 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0366P)² + 0.216P] where P = (F_o² + 2F_c²)/3
1337 reflections	(Δ/σ)_max = 0.002
73 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

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	0.55441 (9)	0.4806 (2)	0.96946 (9)	0.0195 (2)
C2	0.56012 (9)	0.2944 (3)	0.86586 (10)	0.0231 (2)
H2	0.4948	0.1864	0.8337	0.028*
C3	0.66271 (10)	0.2695 (3)	0.81069 (10)	0.0256 (2)
H3	0.6689	0.1441	0.7401	0.031*
C4	0.75625 (10)	0.4310 (3)	0.86036 (10)	0.0244 (2)
H4	0.8274	0.4207	0.8239	0.029*
C5	0.74350 (9)	0.6086 (2)	0.96486 (10)	0.0218 (2)
C6	0.84136 (10)	0.7881 (3)	1.02271 (11)	0.0266 (2)
H6A	0.8128	0.9819	1.0565	0.032*
H6B	0.8951	0.8397	0.9594	0.032*
N1	0.64505 (8)	0.6337 (2)	1.01938 (8)	0.02090 (19)
Cl1	0.91510 (2)	0.57081 (7)	1.14489 (3)	0.02892 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0206 (5)	0.0201 (5)	0.0174 (5)	0.0010 (4)	−0.0015 (4)	0.0029 (4)
C2	0.0229 (5)	0.0259 (5)	0.0199 (5)	0.0006 (4)	−0.0028 (4)	−0.0015 (4)
C3	0.0272 (5)	0.0299 (6)	0.0194 (5)	0.0037 (4)	−0.0004 (4)	−0.0021 (4)
C4	0.0221 (5)	0.0295 (6)	0.0218 (5)	0.0028 (4)	0.0022 (4)	0.0034 (4)
C5	0.0216 (5)	0.0218 (5)	0.0216 (5)	−0.0001 (4)	−0.0014 (4)	0.0048 (4)
C6	0.0232 (5)	0.0254 (5)	0.0309 (6)	−0.0031 (4)	−0.0016 (4)	0.0027 (4)
N1	0.0209 (4)	0.0218 (4)	0.0197 (4)	−0.0003 (3)	−0.0013 (3)	0.0016 (3)
Cl1	0.02356 (16)	0.03444 (18)	0.02793 (17)	−0.00080 (10)	−0.00511 (11)	−0.00197 (10)

Geometric parameters (Å, º) top

C1—N1	1.3447 (14)	C4—C5	1.3929 (16)
C1—C2	1.3958 (15)	C4—H4	0.9500
C1—C1ⁱ	1.489 (2)	C5—N1	1.3390 (14)
C2—C3	1.3861 (15)	C5—C6	1.4989 (15)
C2—H2	0.9500	C6—Cl1	1.8109 (12)
C3—C4	1.3884 (16)	C6—H6A	0.9900
C3—H3	0.9500	C6—H6B	0.9900

N1—C1—C2	122.65 (10)	C5—C4—H4	120.7
N1—C1—C1ⁱ	116.45 (12)	N1—C5—C4	123.24 (10)
C2—C1—C1ⁱ	120.90 (12)	N1—C5—C6	115.74 (10)
C3—C2—C1	118.89 (10)	C4—C5—C6	121.01 (10)
C3—C2—H2	120.6	C5—C6—Cl1	110.80 (8)
C1—C2—H2	120.6	C5—C6—H6A	109.5
C2—C3—C4	118.84 (10)	Cl1—C6—H6A	109.5
C2—C3—H3	120.6	C5—C6—H6B	109.5
C4—C3—H3	120.6	Cl1—C6—H6B	109.5
C3—C4—C5	118.55 (10)	H6A—C6—H6B	108.1
C3—C4—H4	120.7	C5—N1—C1	117.82 (10)

N1—C1—C2—C3	−1.08 (16)	N1—C5—C6—Cl1	86.68 (11)
C1ⁱ—C1—C2—C3	178.82 (12)	C4—C5—C6—Cl1	−93.88 (11)
C1—C2—C3—C4	−0.07 (17)	C4—C5—N1—C1	−0.48 (16)
C2—C3—C4—C5	0.86 (16)	C6—C5—N1—C1	178.95 (9)
C3—C4—C5—N1	−0.62 (16)	C2—C1—N1—C5	1.34 (15)
C3—C4—C5—C6	179.98 (10)	C1ⁱ—C1—N1—C5	−178.57 (11)

Symmetry code: (i) −x+1, −y+1, −z+2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

6,6'-Bis­(chloro­methyl)-2,2'-bi­pyridine

Supporting information

Key indicators

checkCIF/PLATON results

6,6'-Bis(chloromethyl)-2,2'-bipyridine