2,4,6-Tripiperidino-1,3,5-triazine

In the title compound, C₁₈H₃₀N₆, the central triazine ring is planar, with C-N bond lengths 1.3415 (14)-1.3504 (13) Å, N-C-N angles 125.58 (10)-125.97 (9)° and C-N-C angles 113.82 (9)-114.33 (9)°.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.117
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C18H30N6	Z = 2
Mr = 330.48	F(000) = 360
Triclinic, P1	Dx = 1.228 Mg m^−3
a = 8.3527 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8192 (10) Å	Cell parameters from 5270 reflections
c = 12.0219 (12) Å	θ = 2–30°
α = 98.377 (3)°	µ = 0.08 mm^−1
β = 101.455 (3)°	T = 133 K
γ = 108.361 (3)°	Cut tablet, colourless
V = 893.88 (15) Å^3	0.38 × 0.22 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3407 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
Detector resolution: 8.192 pixels mm^-1	h = −11→11
ω– and φ scans	k = −13→13
12279 measured reflections	l = −16→16
4407 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	Riding
S = 1.05	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.0581P] where P = (Fo^2 + 2Fc^2)/3
4407 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.17 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
C1	0.18725 (13)	0.04736 (10)	0.21320 (8)	0.0246 (2)
C2	0.33816 (14)	0.28662 (10)	0.30150 (8)	0.0243 (2)
C3	0.06960 (14)	0.17362 (11)	0.32453 (9)	0.0259 (2)
C4	0.31516 (14)	−0.09231 (12)	0.09208 (10)	0.0300 (2)
H4A	0.3674	−0.1570	0.1299	0.036*
H4B	0.4073	0.0058	0.1071	0.036*
C5	0.24791 (16)	−0.15620 (14)	−0.03807 (10)	0.0386 (3)
H5A	0.3431	−0.1734	−0.0688	0.046*
H5B	0.2112	−0.0848	−0.0771	0.046*
C6	0.09321 (16)	−0.30125 (14)	−0.06577 (10)	0.0394 (3)
H6A	0.0453	−0.3361	−0.1512	0.047*
H6B	0.1331	−0.3769	−0.0356	0.047*
C7	−0.04821 (14)	−0.28013 (12)	−0.01067 (10)	0.0317 (3)
H7A	−0.0980	−0.2138	−0.0479	0.038*
H7B	−0.1433	−0.3762	−0.0241	0.038*
C8	0.02412 (15)	−0.21524 (11)	0.11900 (10)	0.0308 (2)
H8A	−0.0680	−0.1950	0.1518	0.037*
H8B	0.0604	−0.2870	0.1578	0.037*
C9	−0.22720 (15)	0.05333 (12)	0.34689 (10)	0.0326 (3)
H9A	−0.2224	−0.0309	0.2930	0.039*
H9B	−0.3251	0.0808	0.3086	0.039*
C10	−0.25786 (14)	0.00891 (12)	0.45900 (10)	0.0322 (3)
H10A	−0.1664	−0.0284	0.4929	0.039*
H10B	−0.3726	−0.0713	0.4418	0.039*
C11	−0.25376 (15)	0.14000 (13)	0.54648 (10)	0.0326 (3)
H11A	−0.3525	0.1711	0.5159	0.039*
H11B	−0.2668	0.1110	0.6206	0.039*
C12	−0.08223 (14)	0.26768 (12)	0.56851 (9)	0.0293 (2)
H12A	−0.0846	0.3542	0.6209	0.035*
H12B	0.0153	0.2402	0.6075	0.035*
C13	−0.05192 (16)	0.30755 (11)	0.45529 (9)	0.0317 (3)
H13A	−0.1406	0.3477	0.4215	0.038*
H13B	0.0648	0.3846	0.4708	0.038*
C14	0.47647 (14)	0.55506 (11)	0.36704 (9)	0.0282 (2)
H14A	0.5912	0.6213	0.4187	0.034*
H14B	0.3883	0.5450	0.4125	0.034*
C15	0.42725 (14)	0.62080 (11)	0.26373 (9)	0.0277 (2)
H15A	0.4275	0.7207	0.2924	0.033*
H15B	0.3079	0.5591	0.2162	0.033*
C16	0.55606 (16)	0.62956 (12)	0.18868 (10)	0.0323 (3)
H16A	0.6720	0.7022	0.2330	0.039*
H16B	0.5160	0.6638	0.1184	0.039*
C17	0.57258 (14)	0.47957 (12)	0.15190 (9)	0.0291 (2)
H17A	0.4618	0.4109	0.0971	0.035*
H17B	0.6667	0.4906	0.1114	0.035*
C18	0.61390 (13)	0.41662 (11)	0.25816 (9)	0.0279 (2)
H18A	0.6149	0.3164	0.2327	0.034*
H18B	0.7315	0.4790	0.3081	0.034*
N1	0.33687 (11)	0.16378 (9)	0.23397 (7)	0.0258 (2)
N2	0.21014 (12)	0.29855 (9)	0.34978 (7)	0.0273 (2)
N3	0.04970 (12)	0.04516 (9)	0.25566 (7)	0.0269 (2)
N4	0.17390 (12)	−0.07876 (10)	0.14146 (8)	0.0317 (2)
N5	−0.06290 (13)	0.17814 (10)	0.37227 (8)	0.0333 (2)
N6	0.48509 (12)	0.41008 (9)	0.32508 (7)	0.0270 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0302 (5)	0.0214 (5)	0.0201 (5)	0.0066 (4)	0.0067 (4)	0.0037 (4)
C2	0.0312 (5)	0.0213 (5)	0.0173 (5)	0.0067 (4)	0.0037 (4)	0.0048 (4)
C3	0.0357 (6)	0.0212 (5)	0.0190 (5)	0.0066 (4)	0.0088 (4)	0.0041 (4)
C4	0.0263 (5)	0.0260 (5)	0.0361 (6)	0.0085 (4)	0.0096 (4)	0.0023 (4)
C5	0.0380 (6)	0.0406 (6)	0.0346 (6)	0.0076 (5)	0.0191 (5)	0.0022 (5)
C6	0.0380 (7)	0.0397 (6)	0.0301 (6)	0.0037 (5)	0.0127 (5)	−0.0063 (5)
C7	0.0279 (5)	0.0300 (5)	0.0321 (6)	0.0063 (4)	0.0053 (4)	0.0038 (4)
C8	0.0338 (6)	0.0215 (5)	0.0329 (6)	0.0029 (4)	0.0156 (5)	−0.0003 (4)
C9	0.0322 (6)	0.0273 (5)	0.0329 (6)	0.0045 (4)	0.0128 (5)	−0.0025 (4)
C10	0.0272 (5)	0.0280 (5)	0.0407 (6)	0.0053 (4)	0.0157 (5)	0.0061 (5)
C11	0.0310 (6)	0.0373 (6)	0.0303 (6)	0.0101 (5)	0.0151 (4)	0.0049 (5)
C12	0.0300 (6)	0.0312 (5)	0.0264 (5)	0.0112 (4)	0.0094 (4)	0.0016 (4)
C13	0.0426 (6)	0.0222 (5)	0.0299 (6)	0.0096 (4)	0.0149 (5)	0.0012 (4)
C14	0.0361 (6)	0.0200 (5)	0.0222 (5)	0.0034 (4)	0.0075 (4)	0.0001 (4)
C15	0.0336 (6)	0.0250 (5)	0.0249 (5)	0.0119 (4)	0.0085 (4)	0.0017 (4)
C16	0.0425 (6)	0.0308 (5)	0.0311 (6)	0.0170 (5)	0.0160 (5)	0.0118 (4)
C17	0.0306 (5)	0.0318 (5)	0.0296 (6)	0.0133 (4)	0.0140 (4)	0.0073 (4)
C18	0.0240 (5)	0.0231 (5)	0.0324 (6)	0.0059 (4)	0.0035 (4)	0.0036 (4)
N1	0.0291 (5)	0.0210 (4)	0.0241 (4)	0.0060 (3)	0.0058 (4)	0.0031 (3)
N2	0.0359 (5)	0.0207 (4)	0.0215 (4)	0.0050 (4)	0.0093 (4)	0.0022 (3)
N3	0.0326 (5)	0.0215 (4)	0.0233 (4)	0.0051 (3)	0.0104 (4)	0.0014 (3)
N4	0.0317 (5)	0.0227 (4)	0.0353 (5)	0.0019 (4)	0.0166 (4)	−0.0030 (4)
N5	0.0418 (6)	0.0213 (4)	0.0325 (5)	0.0025 (4)	0.0204 (4)	−0.0019 (4)
N6	0.0328 (5)	0.0195 (4)	0.0239 (4)	0.0044 (3)	0.0066 (4)	0.0019 (3)

Geometric parameters (Å, º)

C1—N3	1.3422 (14)	C5—H5A	0.9900
C1—N1	1.3504 (13)	C5—H5B	0.9900
C1—N4	1.3614 (13)	C6—H6A	0.9900
C2—N2	1.3415 (14)	C6—H6B	0.9900
C2—N1	1.3480 (13)	C7—H7A	0.9900
C2—N6	1.3713 (13)	C7—H7B	0.9900
C3—N3	1.3465 (13)	C8—H8A	0.9900
C3—N2	1.3482 (13)	C8—H8B	0.9900
C3—N5	1.3535 (15)	C9—H9A	0.9900
C4—N4	1.4548 (14)	C9—H9B	0.9900
C4—C5	1.5166 (16)	C10—H10A	0.9900
C5—C6	1.5299 (16)	C10—H10B	0.9900
C6—C7	1.5172 (17)	C11—H11A	0.9900
C7—C8	1.5150 (15)	C11—H11B	0.9900
C8—N4	1.4622 (13)	C12—H12A	0.9900
C9—N5	1.4641 (13)	C12—H12B	0.9900
C9—C10	1.5200 (16)	C13—H13A	0.9900
C10—C11	1.5256 (15)	C13—H13B	0.9900
C11—C12	1.5217 (15)	C14—H14A	0.9900
C12—C13	1.5164 (15)	C14—H14B	0.9900
C13—N5	1.4629 (13)	C15—H15A	0.9900
C14—N6	1.4683 (13)	C15—H15B	0.9900
C14—C15	1.5253 (14)	C16—H16A	0.9900
C15—C16	1.5261 (16)	C16—H16B	0.9900
C16—C17	1.5317 (15)	C17—H17A	0.9900
C17—C18	1.5239 (15)	C17—H17B	0.9900
C18—N6	1.4575 (14)	C18—H18A	0.9900
C4—H4A	0.9900	C18—H18B	0.9900
C4—H4B	0.9900
N3—C1—N1	125.97 (9)	N4—C8—H8A	109.6
N3—C1—N4	117.03 (9)	C7—C8—H8A	109.6
N1—C1—N4	116.99 (10)	N4—C8—H8B	109.6
N2—C2—N1	125.97 (9)	C7—C8—H8B	109.6
N2—C2—N6	116.86 (9)	H8A—C8—H8B	108.1
N1—C2—N6	117.15 (10)	N5—C9—H9A	109.7
N3—C3—N2	125.58 (10)	C10—C9—H9A	109.7
N3—C3—N5	117.33 (9)	N5—C9—H9B	109.7
N2—C3—N5	117.09 (9)	C10—C9—H9B	109.7
N4—C4—C5	110.56 (9)	H9A—C9—H9B	108.2
C4—C5—C6	111.20 (10)	C9—C10—H10A	109.5
C7—C6—C5	110.27 (10)	C11—C10—H10A	109.5
C8—C7—C6	111.07 (9)	C9—C10—H10B	109.5
N4—C8—C7	110.49 (9)	C11—C10—H10B	109.5
N5—C9—C10	109.98 (9)	H10A—C10—H10B	108.1
C9—C10—C11	110.55 (9)	C12—C11—H11A	109.6
C12—C11—C10	110.27 (9)	C10—C11—H11A	109.6
C13—C12—C11	110.92 (9)	C12—C11—H11B	109.6
N5—C13—C12	110.61 (9)	C10—C11—H11B	109.6
N6—C14—C15	109.69 (8)	H11A—C11—H11B	108.1
C14—C15—C16	110.58 (9)	C13—C12—H12A	109.5
C15—C16—C17	111.25 (9)	C11—C12—H12A	109.5
C18—C17—C16	110.30 (9)	C13—C12—H12B	109.5
N6—C18—C17	111.00 (8)	C11—C12—H12B	109.5
C2—N1—C1	113.82 (9)	H12A—C12—H12B	108.0
C2—N2—C3	114.33 (9)	N5—C13—H13A	109.5
C1—N3—C3	114.27 (9)	C12—C13—H13A	109.5
C1—N4—C4	122.56 (9)	N5—C13—H13B	109.5
C1—N4—C8	122.15 (9)	C12—C13—H13B	109.5
C4—N4—C8	114.95 (8)	H13A—C13—H13B	108.1
C3—N5—C13	122.56 (9)	N6—C14—H14A	109.7
C3—N5—C9	122.85 (9)	C15—C14—H14A	109.7
C13—N5—C9	114.57 (9)	N6—C14—H14B	109.7
C2—N6—C18	120.33 (8)	C15—C14—H14B	109.7
C2—N6—C14	119.48 (9)	H14A—C14—H14B	108.2
C18—N6—C14	112.82 (8)	C14—C15—H15A	109.5
N4—C4—H4A	109.5	C16—C15—H15A	109.5
C5—C4—H4A	109.5	C14—C15—H15B	109.5
N4—C4—H4B	109.5	C16—C15—H15B	109.5
C5—C4—H4B	109.5	H15A—C15—H15B	108.1
H4A—C4—H4B	108.1	C15—C16—H16A	109.4
C4—C5—H5A	109.4	C17—C16—H16A	109.4
C6—C5—H5A	109.4	C15—C16—H16B	109.4
C4—C5—H5B	109.4	C17—C16—H16B	109.4
C6—C5—H5B	109.4	H16A—C16—H16B	108.0
H5A—C5—H5B	108.0	C18—C17—H17A	109.6
C7—C6—H6A	109.6	C16—C17—H17A	109.6
C5—C6—H6A	109.6	C18—C17—H17B	109.6
C7—C6—H6B	109.6	C16—C17—H17B	109.6
C5—C6—H6B	109.6	H17A—C17—H17B	108.1
H6A—C6—H6B	108.1	N6—C18—H18A	109.4
C8—C7—H7A	109.4	C17—C18—H18A	109.4
C6—C7—H7A	109.4	N6—C18—H18B	109.4
C8—C7—H7B	109.4	C17—C18—H18B	109.4
C6—C7—H7B	109.4	H18A—C18—H18B	108.0
H7A—C7—H7B	108.0
N4—C4—C5—C6	−53.74 (13)	N3—C1—N4—C4	−178.34 (9)
C4—C5—C6—C7	54.34 (14)	N1—C1—N4—C4	2.46 (15)
C5—C6—C7—C8	−54.75 (13)	N3—C1—N4—C8	−5.34 (15)
C6—C7—C8—N4	54.65 (12)	N1—C1—N4—C8	175.46 (9)
N5—C9—C10—C11	55.62 (12)	C5—C4—N4—C1	−130.84 (11)
C9—C10—C11—C12	−55.89 (12)	C5—C4—N4—C8	55.69 (13)
C10—C11—C12—C13	55.10 (12)	C7—C8—N4—C1	130.37 (11)
C11—C12—C13—N5	−54.20 (13)	C7—C8—N4—C4	−56.14 (13)
N6—C14—C15—C16	−56.30 (11)	N3—C3—N5—C13	175.36 (9)
C14—C15—C16—C17	53.87 (12)	N2—C3—N5—C13	−4.87 (15)
C15—C16—C17—C18	−52.59 (12)	N3—C3—N5—C9	−3.42 (16)
C16—C17—C18—N6	54.63 (11)	N2—C3—N5—C9	176.35 (9)
N2—C2—N1—C1	2.27 (14)	C12—C13—N5—C3	−122.67 (11)
N6—C2—N1—C1	−179.14 (8)	C12—C13—N5—C9	56.21 (13)
N3—C1—N1—C2	−1.86 (14)	C10—C9—N5—C3	122.00 (11)
N4—C1—N1—C2	177.27 (9)	C10—C9—N5—C13	−56.87 (13)
N1—C2—N2—C3	−0.85 (15)	N2—C2—N6—C18	−167.25 (8)
N6—C2—N2—C3	−179.45 (8)	N1—C2—N6—C18	14.03 (13)
N3—C3—N2—C2	−1.25 (15)	N2—C2—N6—C14	−19.37 (13)
N5—C3—N2—C2	179.00 (9)	N1—C2—N6—C14	161.91 (8)
N1—C1—N3—C3	0.10 (15)	C17—C18—N6—C2	90.31 (11)
N4—C1—N3—C3	−179.03 (9)	C17—C18—N6—C14	−59.55 (11)
N2—C3—N3—C1	1.60 (15)	C15—C14—N6—C2	−90.17 (11)
N5—C3—N3—C1	−178.65 (9)	C15—C14—N6—C18	59.98 (11)