N,N'-Bis(3,5-dimethyl-1H-pyrazol-1-ylmeth­yl)piperazine

The mol­ecule of the title compound, C₁₆H₂₆N₆, is located on a crystallographic centre of inversion; as a result, there is just one half-mol­ecule in the asymmetric unit. The piperazine ring adopts an ideal chair conformation. The substituents at the piperazine N atoms are in equatorial positions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.034
• wR factor = 0.100
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

N,N'-Bis(3,5-dimethyl-1H-pyrazol-1-ylmethyl)piperazine

Crystal data

C16H26N6	F(000) = 656
Mr = 302.43	Dx = 1.241 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14373 reflections
a = 9.6944 (9) Å	θ = 3.6–25.7°
b = 12.1761 (11) Å	µ = 0.08 mm^−1
c = 13.7141 (12) Å	T = 173 K
V = 1618.8 (3) Å^3	Block, colourless
Z = 4	0.28 × 0.26 × 0.23 mm

Data collection

Stoe IPDS-II two-circle diffractometer	1319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 25.8°, θmin = 3.6°
ω scans	h = −11→11
16864 measured reflections	k = −14→14
1560 independent reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.1979P] where P = (Fo^2 + 2Fc^2)/3
1560 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.19 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
N1	0.63520 (11)	0.75690 (8)	0.57756 (8)	0.0323 (3)
N2	0.53750 (11)	0.83475 (8)	0.55889 (8)	0.0336 (3)
C3	0.52427 (14)	0.89020 (10)	0.64202 (9)	0.0337 (3)
C31	0.42534 (16)	0.98411 (11)	0.64889 (11)	0.0423 (3)
H31A	0.4257	1.0252	0.5874	0.064*
H31B	0.4531	1.0328	0.7023	0.064*
H31C	0.3323	0.9559	0.6614	0.064*
C4	0.61322 (14)	0.84879 (10)	0.71357 (9)	0.0364 (3)
H4	0.6231	0.8745	0.7786	0.044*
C5	0.68335 (13)	0.76330 (10)	0.67056 (9)	0.0345 (3)
C51	0.79386 (15)	0.69068 (11)	0.71012 (11)	0.0434 (3)
H51A	0.7552	0.6181	0.7246	0.065*
H51B	0.8313	0.7229	0.7700	0.065*
H51C	0.8677	0.6832	0.6618	0.065*
C11	0.67623 (14)	0.68471 (10)	0.49670 (9)	0.0345 (3)
H11A	0.6712	0.7276	0.4355	0.041*
H11B	0.7740	0.6639	0.5064	0.041*
N11	0.59721 (11)	0.58543 (8)	0.48357 (8)	0.0311 (3)
C12	0.62058 (14)	0.50220 (10)	0.55841 (9)	0.0343 (3)
H12A	0.5834	0.5281	0.6216	0.041*
H12B	0.7208	0.4894	0.5662	0.041*
C13	0.55008 (14)	0.39611 (10)	0.52938 (10)	0.0337 (3)
H13A	0.5905	0.3684	0.4678	0.040*
H13B	0.5650	0.3400	0.5806	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0304 (6)	0.0320 (5)	0.0345 (6)	−0.0017 (4)	0.0002 (4)	0.0001 (4)
N2	0.0310 (6)	0.0328 (5)	0.0370 (6)	−0.0008 (4)	0.0002 (4)	0.0000 (4)
C3	0.0300 (7)	0.0349 (6)	0.0363 (7)	−0.0077 (5)	0.0037 (5)	−0.0016 (5)
C31	0.0374 (8)	0.0416 (7)	0.0481 (8)	−0.0009 (6)	0.0033 (6)	−0.0076 (6)
C4	0.0360 (7)	0.0417 (6)	0.0314 (6)	−0.0104 (5)	0.0018 (5)	−0.0016 (5)
C5	0.0300 (7)	0.0372 (6)	0.0362 (6)	−0.0094 (5)	−0.0018 (5)	0.0049 (5)
C51	0.0383 (8)	0.0430 (7)	0.0488 (8)	−0.0073 (6)	−0.0095 (6)	0.0076 (6)
C11	0.0325 (7)	0.0347 (6)	0.0363 (6)	−0.0017 (5)	0.0048 (5)	−0.0007 (5)
N11	0.0276 (6)	0.0300 (5)	0.0356 (6)	0.0009 (4)	−0.0002 (4)	0.0013 (4)
C12	0.0302 (7)	0.0349 (6)	0.0377 (7)	0.0025 (5)	−0.0061 (5)	0.0021 (5)
C13	0.0301 (7)	0.0314 (6)	0.0396 (7)	0.0041 (5)	−0.0035 (5)	0.0036 (5)

Geometric parameters (Å, º)

N1—C5	1.3604 (17)	C51—H51B	0.9800
N1—N2	1.3642 (15)	C51—H51C	0.9800
N1—C11	1.4698 (16)	C11—N11	1.4424 (16)
N2—C3	1.3312 (17)	C11—H11A	0.9900
C3—C4	1.4003 (19)	C11—H11B	0.9900
C3—C31	1.4954 (19)	N11—C13^i	1.4563 (17)
C31—H31A	0.9800	N11—C12	1.4601 (16)
C31—H31B	0.9800	C12—C13	1.5147 (17)
C31—H31C	0.9800	C12—H12A	0.9900
C4—C5	1.3761 (19)	C12—H12B	0.9900
C4—H4	0.9500	C13—N11^i	1.4563 (17)
C5—C51	1.4913 (19)	C13—H13A	0.9900
C51—H51A	0.9800	C13—H13B	0.9900
C5—N1—N2	111.99 (10)	H51A—C51—H51C	109.5
C5—N1—C11	130.44 (11)	H51B—C51—H51C	109.5
N2—N1—C11	117.50 (10)	N11—C11—N1	116.85 (10)
C3—N2—N1	104.99 (10)	N11—C11—H11A	108.1
N2—C3—C4	110.99 (12)	N1—C11—H11A	108.1
N2—C3—C31	120.24 (12)	N11—C11—H11B	108.1
C4—C3—C31	128.77 (12)	N1—C11—H11B	108.1
C3—C31—H31A	109.5	H11A—C11—H11B	107.3
C3—C31—H31B	109.5	C11—N11—C13^i	113.99 (10)
H31A—C31—H31B	109.5	C11—N11—C12	114.30 (10)
C3—C31—H31C	109.5	C13^i—N11—C12	110.19 (10)
H31A—C31—H31C	109.5	N11—C12—C13	109.71 (10)
H31B—C31—H31C	109.5	N11—C12—H12A	109.7
C5—C4—C3	106.03 (11)	C13—C12—H12A	109.7
C5—C4—H4	127.0	N11—C12—H12B	109.7
C3—C4—H4	127.0	C13—C12—H12B	109.7
N1—C5—C4	106.01 (11)	H12A—C12—H12B	108.2
N1—C5—C51	123.61 (12)	N11^i—C13—C12	110.05 (10)
C4—C5—C51	130.35 (12)	N11^i—C13—H13A	109.7
C5—C51—H51A	109.5	C12—C13—H13A	109.7
C5—C51—H51B	109.5	N11^i—C13—H13B	109.7
H51A—C51—H51B	109.5	C12—C13—H13B	109.7
C5—C51—H51C	109.5	H13A—C13—H13B	108.2
C5—N1—N2—C3	−0.30 (13)	C3—C4—C5—N1	0.01 (13)
C11—N1—N2—C3	−177.62 (10)	C3—C4—C5—C51	178.04 (13)
N1—N2—C3—C4	0.29 (14)	C5—N1—C11—N11	94.59 (16)
N1—N2—C3—C31	179.46 (11)	N2—N1—C11—N11	−88.67 (13)
N2—C3—C4—C5	−0.19 (14)	N1—C11—N11—C13^i	56.56 (14)
C31—C3—C4—C5	−179.27 (13)	N1—C11—N11—C12	−71.42 (14)
N2—N1—C5—C4	0.18 (14)	C11—N11—C12—C13	−171.42 (10)
C11—N1—C5—C4	177.07 (11)	C13^i—N11—C12—C13	58.69 (15)
N2—N1—C5—C51	−178.02 (11)	N11—C12—C13—N11^i	−58.61 (15)
C11—N1—C5—C51	−1.1 (2)	C12^i—C13^i—N11—C12	−58.89 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.