Buy article online - an online subscription or single-article purchase is required to access this article.
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.
Supporting information
CCDC reference: 239292
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
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 |
Mr = 253.12 | Dx = 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 | Rint = 0.013 |
ω scans | θmax = 28.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | h = −15→15 |
Tmin = 0.755, Tmax = 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(Fo2) + (0.0366P)2 + 0.216P] where P = (Fo2 + 2Fc2)/3 |
1337 reflections | (Δ/σ)max = 0.002 |
73 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −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 | Uiso*/Ueq | |
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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.