1,4-Bis(6-chloro­pyridin-3-ylmeth­yl)piperazine

The complete mol­ecule of the title compound, C₁₆H₁₈Cl₂N₄, is generated by inversion symmetry. The piperazine ring displays a normal chair conformation. Weak C—H...N inter­actions between neighbouring pyridine rings help to stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.041
• wR factor = 0.144
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,4-Bis(6-chloropyridin-3-ylmethyl)piperazine

Crystal data

C16H18Cl2N4	Z = 1
Mr = 337.24	F(000) = 176
Triclinic, P1	Dx = 1.355 Mg m^−3
Hall symbol: -P 1	Melting point = 415–416 K
a = 5.802 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.144 (6) Å	Cell parameters from 3095 reflections
c = 12.473 (7) Å	θ = 3.3–25.0°
α = 81.72 (4)°	µ = 0.39 mm^−1
β = 83.78 (4)°	T = 295 K
γ = 70.31 (4)°	Block, colourless
V = 413.4 (6) Å^3	0.32 × 0.28 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1488 independent reflections
Radiation source: fine-focus sealed tube	1230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.00 pixels mm^-1	θmax = 25.2°, θmin = 3.3°
ω scans	h = −6→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→7
Tmin = 0.880, Tmax = 0.930	l = −14→14
3363 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0782P)^2 + 0.0716P] where P = (Fo^2 + 2Fc^2)/3
1488 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.86934 (12)	0.25073 (11)	0.06309 (6)	0.0657 (3)
N1	0.4612 (4)	0.3120 (3)	0.18259 (17)	0.0507 (5)
N2	0.0276 (3)	0.9352 (3)	0.39156 (14)	0.0388 (4)
C1	0.6139 (4)	0.4195 (4)	0.13579 (18)	0.0426 (5)
C2	0.5844 (4)	0.6497 (4)	0.1417 (2)	0.0490 (6)
H2	0.6985	0.7171	0.1074	0.059*
C3	0.3816 (4)	0.7757 (4)	0.19982 (19)	0.0484 (6)
H3	0.3564	0.9314	0.2057	0.058*
C4	0.2129 (4)	0.6715 (4)	0.25021 (17)	0.0405 (5)
C5	0.2649 (4)	0.4394 (4)	0.23894 (19)	0.0473 (6)
H5	0.1554	0.3662	0.2730	0.057*
C6	−0.0172 (4)	0.8043 (4)	0.31156 (18)	0.0462 (6)
H6A	−0.1285	0.9115	0.2603	0.055*
H6B	−0.0968	0.6960	0.3484	0.055*
C7	0.1665 (4)	0.7830 (4)	0.47861 (19)	0.0520 (6)
H7A	0.3244	0.6891	0.4489	0.062*
H7B	0.0795	0.6789	0.5132	0.062*
C8	0.2053 (4)	0.9195 (5)	0.5616 (2)	0.0567 (7)
H8A	0.2982	0.8130	0.6189	0.068*
H8B	0.3001	1.0172	0.5278	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0607 (5)	0.0620 (5)	0.0649 (5)	−0.0068 (3)	0.0132 (3)	−0.0228 (3)
N1	0.0593 (12)	0.0365 (10)	0.0570 (12)	−0.0162 (9)	0.0033 (9)	−0.0117 (8)
N2	0.0373 (9)	0.0423 (10)	0.0356 (9)	−0.0103 (7)	0.0025 (7)	−0.0104 (7)
C1	0.0461 (12)	0.0411 (12)	0.0392 (11)	−0.0099 (9)	−0.0022 (9)	−0.0104 (9)
C2	0.0517 (13)	0.0506 (14)	0.0499 (13)	−0.0250 (10)	0.0087 (10)	−0.0110 (10)
C3	0.0574 (14)	0.0382 (12)	0.0552 (14)	−0.0222 (10)	0.0048 (10)	−0.0135 (10)
C4	0.0461 (12)	0.0435 (12)	0.0348 (11)	−0.0173 (9)	−0.0019 (8)	−0.0080 (8)
C5	0.0533 (13)	0.0432 (12)	0.0501 (13)	−0.0238 (10)	0.0050 (10)	−0.0071 (10)
C6	0.0435 (12)	0.0532 (13)	0.0453 (12)	−0.0180 (10)	0.0004 (9)	−0.0130 (10)
C7	0.0541 (14)	0.0474 (13)	0.0434 (13)	0.0005 (10)	−0.0038 (10)	−0.0118 (10)
C8	0.0410 (12)	0.0722 (16)	0.0479 (13)	0.0009 (11)	−0.0056 (10)	−0.0232 (12)

Geometric parameters (Å, º)

Cl—C1	1.743 (3)	C4—C5	1.379 (3)
N1—C1	1.316 (3)	C4—C6	1.503 (3)
N1—C5	1.338 (3)	C5—H5	0.9300
N2—C6	1.462 (3)	C6—H6A	0.9700
N2—C7	1.447 (3)	C6—H6B	0.9700
N2—C8^i	1.459 (3)	C7—C8	1.501 (4)
C1—C2	1.378 (4)	C7—H7A	0.9700
C2—C3	1.369 (3)	C7—H7B	0.9700
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.391 (3)	C8—H8B	0.9700
C3—H3	0.9300
C1—N1—C5	116.3 (2)	N2—C6—C4	113.23 (18)
C7—N2—C8^i	108.46 (18)	N2—C6—H6A	108.9
C7—N2—C6	111.81 (19)	C4—C6—H6A	108.9
C8^i—N2—C6	109.96 (18)	N2—C6—H6B	108.9
N1—C1—C2	124.6 (2)	C4—C6—H6B	108.9
N1—C1—Cl	115.78 (18)	H6A—C6—H6B	107.7
C2—C1—Cl	119.62 (19)	N2—C7—C8	111.2 (2)
C3—C2—C1	117.7 (2)	N2—C7—H7A	109.4
C3—C2—H2	121.1	C8—C7—H7A	109.4
C1—C2—H2	121.1	N2—C7—H7B	109.4
C2—C3—C4	120.1 (2)	C8—C7—H7B	109.4
C2—C3—H3	119.9	H7A—C7—H7B	108.0
C4—C3—H3	119.9	N2^i—C8—C7	111.5 (2)
C5—C4—C3	116.4 (2)	N2^i—C8—H8A	109.3
C5—C4—C6	121.3 (2)	C7—C8—H8A	109.3
C3—C4—C6	122.2 (2)	N2^i—C8—H8B	109.3
N1—C5—C4	124.8 (2)	C7—C8—H8B	109.3
N1—C5—H5	117.6	H8A—C8—H8B	108.0
C4—C5—H5	117.6
C5—N1—C1—C2	0.3 (3)	C6—C4—C5—N1	177.6 (2)
C5—N1—C1—Cl	179.78 (16)	C7—N2—C6—C4	−66.1 (2)
N1—C1—C2—C3	−0.4 (4)	C8^i—N2—C6—C4	173.32 (19)
Cl—C1—C2—C3	−179.85 (17)	C5—C4—C6—N2	130.6 (2)
C1—C2—C3—C4	−0.2 (4)	C3—C4—C6—N2	−50.9 (3)
C2—C3—C4—C5	0.8 (3)	C8^i—N2—C7—C8	−57.1 (3)
C2—C3—C4—C6	−177.8 (2)	C6—N2—C7—C8	−178.5 (2)
C1—N1—C5—C4	0.4 (3)	N2—C7—C8—N2^i	58.8 (3)
C3—C4—C5—N1	−1.0 (3)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1^ii	0.93	2.58	3.452 (3)	157

Symmetry code: (ii) x, y+1, z.