Bis[4-(2-methyl-2-propen­yl)piperazin-1-yl]methane

The title compound, C₁₇H₃₂N₄, contains two piperazine heterocycles, which are methyl­ene bridged. The rings have chair conformations, with all substituents equatorial.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.083
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N12    -   C16     ..       7.17 su

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C6      ..       5.72 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C9      ..       6.17 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C3      ..       5.83 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

Bis[4-(2-methyl-2-propenyl)piperazin-1-yl]methane

Crystal data

C17H32N4	Z = 2
Mr = 292.47	F(000) = 324
Triclinic, P1	Dx = 1.027 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.257 (2) Å	Cell parameters from 6881 reflections
b = 11.719 (3) Å	θ = 3.1–25.2°
c = 13.392 (5) Å	µ = 0.06 mm^−1
α = 90.450 (13)°	T = 291 K
β = 101.719 (8)°	Block, colourless
γ = 100.067 (15)°	0.20 × 0.15 × 0.15 mm
V = 945.7 (5) Å^3

Data collection

Nonius KappaCCD diffractometer	1123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 25.2°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −7→7
498 frames via ω–rotation (Δω=1°) and two times 60 s per frame (four sets at different κ–angles) scans	k = −13→14
6681 measured reflections	l = −15→15
3297 independent 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.01	w = [exp{4.20(sinθ/λ)^2}]/[σ^2(Fo^2)]
3297 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.09 e Å^−3
0 restraints	Δρmin = −0.11 e Å^−3

Special details

Experimental. ¹H NMR (500 MHz, CDCl₃): δ 1.43 (s, 9H), 1.72 (s, 3H), 2.29 (4H), 2.83 (s, 2H). 3.39 (t, 4H, J = 4.7 Hz), 4.83 (s, 2H), 4.84 (s, 2H); ¹³C NMR (125 MHz, CDCl₃): δ 20.8 (CH₃), 28.4 (CH₃), 50.7 (CH₂), 52.9 (CH₂), 65.3 (CH₂), 79.4 (Cq), 113.1 (CH₂), 142.4 (Cq), 154.8 (Cq); IR (KBr plate), ν (cm^-1): 897 (m), 1009 (m), 1122 (s), 1168 (s), 1244 (s), 1362 (m), 1419 (s), 1696 (vs), 2801 (m), 2940 (s), 2980 (m); MS (FAB+ LR), m/z (%): (M)⁺, 240.0?(65); exact mass (FAB + HR): (M)⁺, 240.1852 ?(85) (calculated for C₁₃H₂₄N₂O₂: 240.1838).

¹H NMR (500 MHz, CDCl₃): δ 1.48 (s, 1H), 1.64 (s, 3H), 2.0–2.5 (4H), 2.74 (s, 2H), 2.77 (4H), 4.74 (s, 2H), 4.77 (s, 2H); ¹³C NMR (125 MHz, CDCl₃): δ 20.7 (CH₃), 46.0 (CH₂), 54.5 (CH₂), 65.8 (CH₂), 112.6 (CH₂), 142.5 (Cq); IR (KBr plate), ν (cm^-1): 805 (m), 896 (s), 1014 (m), 1142 (s), 1370 (m), 1455 (s), 1651 (m), 2805 (s), 2940 (s), 2968 (s), 3073 (m) 3283 (w); MS (FAB+ LR), m/z (%): 141.1 (M + H⁺), (25); exact mass (FAB + HR): 141.1416 (M + H⁺), (100) (calculated for C₈H₁₇N₂: 141.1392).

¹H NMR (500 MHz, CDCl₃): δ 1.71 (s, 3H), 2.28–2.60 (16H), 2.84 (s, 4H), 2.9 (s, 2H), 4.81 (s, 2H), 4.84 (s, 2H); ¹³C NMR (125 MHz, CDCl₃): δ 20.9 (CH₃), 51.6 (CH₂), 53.2 (CH₂), 65.4 (CH₂), 81.1 (CH₂), 112.7 (CH₂), 142.8 (Cq); IR (KBr plate), ν (cm^-1): 831 (m), 899 (vs), 1012 (s), 1049 (m), 1119 (m), 1147 (vs), 1166 (s), 1282 (s), 1342 (m), 1371 (m), 1456 (s), 1647 (m), 2758 (m), 2802 (s), 2939 (s), 2964 (s), 3074 (w); MS (FAB + LR), m/z (%): 291.4 (M + H⁺), (15); exact mass (FAB + HR): 291.2563 (M - H⁺), (100) (calculated for C₁₇H₃₁N₄: 291.2548).

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	0.3971 (3)	1.20091 (14)	0.61737 (13)	0.0596 (5)
N2	0.3116 (2)	1.01685 (13)	0.75165 (13)	0.0527 (5)
N11	−0.1595 (2)	0.68818 (13)	0.90323 (13)	0.0544 (5)
N12	0.1055 (2)	0.90230 (12)	0.86038 (12)	0.0502 (5)
C1	0.7059 (4)	1.2833 (2)	0.4303 (2)	0.1042 (9)
H1A	0.8448	1.3225	0.4238	0.125*
H1B	0.6301	1.2234	0.3837	0.125*
C2	0.7310 (4)	1.40858 (19)	0.5829 (2)	0.1124 (10)
H2A	0.8735	1.4407	0.5691	0.169*
H2B	0.7499	1.3783	0.6499	0.169*
H2C	0.6423	1.4681	0.5794	0.169*
C3	0.6170 (4)	1.3126 (2)	0.5051 (2)	0.0730 (7)
C4	0.3933 (3)	1.24962 (19)	0.51690 (17)	0.0826 (8)
H4A	0.2892	1.3029	0.5061	0.099*
H4B	0.3410	1.1874	0.4648	0.099*
C5	0.1726 (3)	1.15719 (18)	0.63186 (17)	0.0749 (7)
H5A	0.0997	1.0963	0.5805	0.090*
H5B	0.0873	1.2193	0.6241	0.090*
C6	0.1820 (3)	1.11001 (17)	0.73703 (17)	0.0686 (7)
H6A	0.2484	1.1721	0.7882	0.082*
H6B	0.0325	1.0807	0.7460	0.082*
C7	0.5355 (3)	1.06116 (16)	0.73701 (16)	0.0643 (6)
H7A	0.6220	0.9995	0.7452	0.077*
H7B	0.6077	1.1226	0.7879	0.077*
C8	0.5246 (3)	1.10713 (17)	0.63196 (16)	0.0675 (7)
H8A	0.6738	1.1354	0.6222	0.081*
H8B	0.4561	1.0448	0.5813	0.081*
C9	0.3204 (3)	0.96918 (16)	0.85167 (16)	0.0608 (6)
H9A	0.3646	1.0319	0.9035	0.073*
H9B	0.4311	0.9195	0.8636	0.073*
C11	−0.6125 (4)	0.47358 (19)	0.7867 (2)	0.0988 (9)
H11A	−0.6439	0.4026	0.7504	0.119*
H11B	−0.7138	0.5239	0.7757	0.119*
C12	−0.2518 (4)	0.42637 (17)	0.87620 (18)	0.0926 (8)
H12A	−0.2998	0.3576	0.8323	0.139*
H12B	−0.2331	0.4053	0.9462	0.139*
H12C	−0.1131	0.4671	0.8640	0.139*
C13	−0.4226 (4)	0.50311 (19)	0.85455 (18)	0.0674 (7)
C14	−0.3672 (3)	0.61601 (16)	0.91652 (16)	0.0663 (6)
H14A	−0.4873	0.6589	0.8969	0.080*
H14B	−0.3556	0.5997	0.9881	0.080*
C15	−0.1805 (3)	0.72908 (16)	0.79939 (15)	0.0597 (6)
H15A	−0.2968	0.7752	0.7858	0.072*
H15B	−0.2207	0.6632	0.7508	0.072*
C16	0.0372 (3)	0.80158 (16)	0.78711 (15)	0.0585 (6)
H16A	0.1514	0.7540	0.7975	0.070*
H16B	0.0217	0.8285	0.7181	0.070*
C17	0.1222 (3)	0.86266 (15)	0.96475 (15)	0.0571 (6)
H17A	0.1584	0.9292	1.0126	0.069*
H17B	0.2401	0.8177	0.9804	0.069*
C18	−0.0957 (3)	0.78876 (16)	0.97590 (15)	0.0601 (6)
H18A	−0.0816	0.7621	1.0449	0.072*
H18B	−0.2113	0.8355	0.9645	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0492 (11)	0.0679 (12)	0.0641 (14)	0.0111 (9)	0.0162 (10)	0.0240 (10)
N2	0.0458 (11)	0.0518 (11)	0.0606 (14)	0.0063 (8)	0.0127 (9)	0.0157 (9)
N11	0.0650 (12)	0.0469 (11)	0.0523 (13)	0.0031 (9)	0.0205 (10)	0.0065 (10)
N12	0.0546 (11)	0.0454 (10)	0.0466 (12)	0.0004 (8)	0.0087 (9)	0.0033 (9)
C1	0.095 (2)	0.141 (2)	0.075 (2)	0.0075 (17)	0.0272 (17)	0.0267 (19)
C2	0.127 (2)	0.089 (2)	0.120 (3)	−0.0124 (16)	0.051 (2)	0.0069 (19)
C3	0.0695 (17)	0.0866 (19)	0.0661 (19)	0.0138 (14)	0.0203 (15)	0.0315 (15)
C4	0.0743 (18)	0.1015 (19)	0.072 (2)	0.0124 (13)	0.0161 (14)	0.0354 (15)
C5	0.0529 (15)	0.0886 (17)	0.086 (2)	0.0164 (12)	0.0175 (14)	0.0319 (14)
C6	0.0534 (14)	0.0748 (16)	0.0833 (19)	0.0140 (12)	0.0244 (13)	0.0262 (14)
C7	0.0540 (14)	0.0650 (15)	0.0788 (19)	0.0149 (11)	0.0209 (13)	0.0221 (13)
C8	0.0623 (15)	0.0684 (15)	0.0781 (19)	0.0114 (12)	0.0290 (14)	0.0152 (13)
C9	0.0549 (14)	0.0538 (13)	0.0694 (18)	0.0034 (10)	0.0083 (12)	0.0117 (12)
C11	0.092 (2)	0.0824 (18)	0.108 (2)	−0.0106 (14)	0.0114 (18)	0.0112 (16)
C12	0.115 (2)	0.0598 (16)	0.104 (2)	0.0133 (14)	0.0266 (17)	0.0098 (15)
C13	0.0734 (17)	0.0551 (15)	0.0726 (19)	−0.0044 (13)	0.0256 (15)	0.0144 (14)
C14	0.0707 (15)	0.0571 (14)	0.0740 (17)	0.0012 (11)	0.0306 (13)	0.0122 (13)
C15	0.0670 (15)	0.0541 (14)	0.0558 (16)	0.0019 (11)	0.0154 (12)	0.0049 (12)
C16	0.0667 (15)	0.0579 (14)	0.0499 (15)	0.0035 (11)	0.0165 (12)	0.0079 (12)
C17	0.0657 (15)	0.0539 (14)	0.0497 (16)	0.0080 (11)	0.0099 (12)	0.0043 (11)
C18	0.0718 (15)	0.0597 (14)	0.0522 (15)	0.0117 (11)	0.0204 (12)	0.0077 (12)

Geometric parameters (Å, º)

N1—C8	1.459 (2)	C7—C8	1.503 (3)
N1—C5	1.461 (2)	C7—H7A	0.9700
N1—C4	1.463 (2)	C7—H7B	0.9700
N2—C9	1.450 (2)	C8—H8A	0.9700
N2—C7	1.459 (2)	C8—H8B	0.9700
N2—C6	1.462 (2)	C9—H9A	0.9700
N11—C15	1.463 (2)	C9—H9B	0.9700
N11—C14	1.465 (2)	C11—C13	1.330 (3)
N11—C18	1.468 (2)	C11—H11A	0.9300
N12—C9	1.460 (2)	C11—H11B	0.9300
N12—C17	1.466 (2)	C12—C13	1.500 (3)
N12—C16	1.474 (2)	C12—H12A	0.9600
C1—C3	1.311 (3)	C12—H12B	0.9600
C1—H1A	0.9300	C12—H12C	0.9600
C1—H1B	0.9300	C13—C14	1.505 (3)
C2—C3	1.503 (3)	C14—H14A	0.9700
C2—H2A	0.9600	C14—H14B	0.9700
C2—H2B	0.9600	C15—C16	1.514 (2)
C2—H2C	0.9600	C15—H15A	0.9700
C3—C4	1.503 (3)	C15—H15B	0.9700
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—C6	1.511 (3)	C17—C18	1.518 (2)
C5—H5A	0.9700	C17—H17A	0.9700
C5—H5B	0.9700	C17—H17B	0.9700
C6—H6A	0.9700	C18—H18A	0.9700
C6—H6B	0.9700	C18—H18B	0.9700
C8—N1—C5	108.91 (16)	N1—C8—H8B	109.4
C8—N1—C4	111.63 (18)	C7—C8—H8B	109.4
C5—N1—C4	111.16 (17)	H8A—C8—H8B	108.0
C9—N2—C7	110.17 (15)	N2—C9—N12	111.33 (16)
C9—N2—C6	112.05 (17)	N2—C9—H9A	109.4
C7—N2—C6	109.13 (15)	N12—C9—H9A	109.4
C15—N11—C14	110.91 (16)	N2—C9—H9B	109.4
C15—N11—C18	109.00 (15)	N12—C9—H9B	109.4
C14—N11—C18	110.93 (16)	H9A—C9—H9B	108.0
C9—N12—C17	108.54 (16)	C13—C11—H11A	120.0
C9—N12—C16	111.43 (16)	C13—C11—H11B	120.0
C17—N12—C16	109.73 (15)	H11A—C11—H11B	120.0
C3—C1—H1A	120.0	C13—C12—H12A	109.5
C3—C1—H1B	120.0	C13—C12—H12B	109.5
H1A—C1—H1B	120.0	H12A—C12—H12B	109.5
C3—C2—H2A	109.5	C13—C12—H12C	109.5
C3—C2—H2B	109.5	H12A—C12—H12C	109.5
H2A—C2—H2B	109.5	H12B—C12—H12C	109.5
C3—C2—H2C	109.5	C11—C13—C12	122.9 (2)
H2A—C2—H2C	109.5	C11—C13—C14	121.7 (2)
H2B—C2—H2C	109.5	C12—C13—C14	115.4 (2)
C1—C3—C2	122.6 (2)	N11—C14—C13	112.95 (17)
C1—C3—C4	120.6 (3)	N11—C14—H14A	109.0
C2—C3—C4	116.8 (2)	C13—C14—H14A	109.0
N1—C4—C3	112.84 (19)	N11—C14—H14B	109.0
N1—C4—H4A	109.0	C13—C14—H14B	109.0
C3—C4—H4A	109.0	H14A—C14—H14B	107.8
N1—C4—H4B	109.0	N11—C15—C16	109.88 (17)
C3—C4—H4B	109.0	N11—C15—H15A	109.7
H4A—C4—H4B	107.8	C16—C15—H15A	109.7
N1—C5—C6	109.86 (17)	N11—C15—H15B	109.7
N1—C5—H5A	109.7	C16—C15—H15B	109.7
C6—C5—H5A	109.7	H15A—C15—H15B	108.2
N1—C5—H5B	109.7	N12—C16—C15	111.46 (17)
C6—C5—H5B	109.7	N12—C16—H16A	109.3
H5A—C5—H5B	108.2	C15—C16—H16A	109.3
N2—C6—C5	111.09 (18)	N12—C16—H16B	109.3
N2—C6—H6A	109.4	C15—C16—H16B	109.3
C5—C6—H6A	109.4	H16A—C16—H16B	108.0
N2—C6—H6B	109.4	N12—C17—C18	110.20 (17)
C5—C6—H6B	109.4	N12—C17—H17A	109.6
H6A—C6—H6B	108.0	C18—C17—H17A	109.6
N2—C7—C8	109.67 (17)	N12—C17—H17B	109.6
N2—C7—H7A	109.7	C18—C17—H17B	109.6
C8—C7—H7A	109.7	H17A—C17—H17B	108.1
N2—C7—H7B	109.7	N11—C18—C17	111.48 (16)
C8—C7—H7B	109.7	N11—C18—H18A	109.3
H7A—C7—H7B	108.2	C17—C18—H18A	109.3
N1—C8—C7	111.17 (18)	N11—C18—H18B	109.3
N1—C8—H8A	109.4	C17—C18—H18B	109.3
C7—C8—H8A	109.4	H18A—C18—H18B	108.0
C8—N1—C4—C3	−67.4 (2)	C17—N12—C9—N2	−176.62 (15)
C5—N1—C4—C3	170.77 (19)	C16—N12—C9—N2	62.4 (2)
C1—C3—C4—N1	124.0 (2)	C15—N11—C14—C13	67.0 (2)
C2—C3—C4—N1	−55.6 (3)	C18—N11—C14—C13	−171.69 (17)
C8—N1—C5—C6	57.9 (2)	C11—C13—C14—N11	−122.4 (2)
C4—N1—C5—C6	−178.73 (18)	C12—C13—C14—N11	58.7 (2)
C9—N2—C6—C5	−179.23 (16)	C14—N11—C15—C16	−179.00 (16)
C7—N2—C6—C5	58.5 (2)	C18—N11—C15—C16	58.6 (2)
N1—C5—C6—N2	−58.7 (2)	C9—N12—C16—C15	177.38 (17)
C9—N2—C7—C8	178.34 (17)	C17—N12—C16—C15	57.1 (2)
C6—N2—C7—C8	−58.2 (2)	N11—C15—C16—N12	−58.9 (2)
C5—N1—C8—C7	−59.3 (2)	C9—N12—C17—C18	−177.85 (15)
C4—N1—C8—C7	177.59 (16)	C16—N12—C17—C18	−55.9 (2)
N2—C7—C8—N1	59.9 (2)	C15—N11—C18—C17	−59.0 (2)
C7—N2—C9—N12	−167.72 (16)	C14—N11—C18—C17	178.57 (17)
C6—N2—C9—N12	70.6 (2)	N12—C17—C18—N11	58.1 (2)