Self-assembly of 4,6-dipiperidino-1,3,5-triazin-2(1H)-one

The mol­ecules in the crystal structure of the title compound, C₁₃H₂₁N₅O, are linked into centrosymmetric dimers through N—H...O=C hydrogen bonds. The piperidine substituents adopt a slightly distorted chair conformation, with an almost planar environment of the N atoms.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.081
• wR factor = 0.218
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86

Author Response: All the available reflections up to theta=67\%, using the Seifert four-circle diffractometer (see experimental) were recorded. 150 out of 2390 reflections correspond to extinctions and 2130 were independent reflections.

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           66.70
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2130
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2485
           Completeness (_total/calc)             85.71%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.86

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.05
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C8     -   C9     ...       1.43 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H142    ..       1.99 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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: XRD3000-S (Seifert, 1996); cell refinement: LSUCRE (Appleman, 1984); data reduction: reference?; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal3.6 (Hall et al., 1999); software used to prepare material for publication: reference?.

4,6-dipiperidino-1,3,5-triazin-2(1H)-one

Crystal data

C13H21N5O	F(000) = 568
Mr = 263.35	Dx = 1.249 Mg m^−3
Monoclinic, P21/n	Melting point: 477 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54180 Å
a = 11.449 (2) Å	Cell parameters from 32 reflections
b = 11.2395 (17) Å	θ = 2–45°
c = 11.918 (3) Å	µ = 0.67 mm^−1
β = 114.040 (16)°	T = 293 K
V = 1400.6 (5) Å^3	Prism, colourless
Z = 4	0.40 × 0.23 × 0.17 mm

Data collection

Four-circle diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 66.7°, θmin = 4.5°
Graphite monochromator	h = −13→12
ω/2θ scans	k = 0→12
2390 measured reflections	l = 0→13
2130 independent reflections	2 standard reflections every 100 min
1170 reflections with I > 2σ(I)	intensity decay: 5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.081	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.218	w = 1/[σ^2(Fo^2) + (0.0742P)^2 + 1.7012P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2130 reflections	Δρmax = 0.41 e Å^−3
176 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (5)

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
N3	0.2848 (3)	0.3841 (4)	0.0402 (4)	0.0616 (11)
C4	0.3901 (4)	0.4477 (5)	0.1083 (4)	0.0577 (13)
N5	0.3941 (3)	0.5598 (3)	0.1490 (3)	0.0564 (11)
C6	0.2825 (4)	0.6128 (4)	0.1193 (4)	0.0533 (12)
N1	0.1716 (3)	0.5544 (4)	0.0504 (4)	0.0588 (12)
H1	0.104 (4)	0.581 (4)	0.036 (5)	0.071*
C2	0.1732 (4)	0.4371 (5)	0.0132 (4)	0.0547 (12)
N7	0.5030 (3)	0.3921 (4)	0.1385 (4)	0.0760 (14)
C8	0.5151 (5)	0.2773 (5)	0.0860 (6)	0.0894 (19)
H81	0.4321	0.2387	0.0516	0.107*
H82	0.5421	0.2906	0.0197	0.107*
C9	0.6048 (5)	0.2004 (5)	0.1750 (6)	0.0903 (19)
H91	0.6167	0.1299	0.1339	0.108*
H92	0.5698	0.1752	0.2329	0.108*
C10	0.7336 (5)	0.2585 (5)	0.2452 (6)	0.0912 (19)
H101	0.7870	0.2064	0.3109	0.109*
H102	0.7761	0.2717	0.1904	0.109*
C11	0.7161 (5)	0.3752 (5)	0.2979 (6)	0.092 (2)
H111	0.6862	0.3600	0.3619	0.111*
H112	0.7982	0.4150	0.3354	0.111*
C12	0.6263 (4)	0.4532 (5)	0.2069 (6)	0.0876 (19)
H121	0.6621	0.4790	0.1498	0.105*
H122	0.6119	0.5232	0.2471	0.105*
N13	0.2783 (3)	0.7246 (4)	0.1549 (4)	0.0733 (13)
C14	0.1634 (5)	0.7990 (5)	0.1160 (6)	0.094 (2)
H141	0.1462	0.8201	0.1868	0.113*
H142	0.0904	0.7552	0.0588	0.113*
C15	0.1834 (6)	0.9097 (5)	0.0555 (6)	0.097 (2)
H151	0.1917	0.8882	−0.0198	0.116*
H152	0.1091	0.9608	0.0339	0.116*
C16	0.3004 (6)	0.9766 (5)	0.1376 (6)	0.0893 (18)
H161	0.2875	1.0076	0.2076	0.107*
H162	0.3141	1.0435	0.0929	0.107*
C17	0.4173 (5)	0.8972 (5)	0.1822 (6)	0.0881 (19)
H171	0.4390	0.8774	0.1138	0.106*
H172	0.4891	0.9396	0.2429	0.106*
C18	0.3939 (5)	0.7853 (5)	0.2379 (5)	0.0821 (18)
H181	0.4666	0.7325	0.2576	0.098*
H182	0.3858	0.8043	0.3138	0.098*
O19	0.0683 (3)	0.3886 (3)	−0.0442 (3)	0.0732 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N3	0.048 (2)	0.061 (3)	0.070 (3)	0.000 (2)	0.0188 (19)	−0.010 (2)
C4	0.044 (3)	0.058 (3)	0.064 (3)	−0.003 (2)	0.016 (2)	−0.006 (3)
N5	0.044 (2)	0.052 (3)	0.071 (3)	0.0021 (18)	0.0201 (18)	−0.005 (2)
C6	0.050 (3)	0.052 (3)	0.057 (3)	0.001 (2)	0.021 (2)	0.006 (2)
N1	0.038 (2)	0.063 (3)	0.071 (3)	−0.001 (2)	0.018 (2)	−0.005 (2)
C2	0.049 (3)	0.064 (3)	0.054 (3)	−0.004 (2)	0.024 (2)	−0.006 (3)
N7	0.042 (2)	0.055 (3)	0.108 (3)	0.0022 (19)	0.006 (2)	−0.020 (2)
C8	0.070 (3)	0.066 (4)	0.118 (5)	−0.002 (3)	0.024 (3)	−0.025 (4)
C9	0.086 (4)	0.056 (4)	0.114 (5)	0.009 (3)	0.025 (4)	−0.007 (3)
C10	0.067 (3)	0.071 (4)	0.111 (5)	0.015 (3)	0.011 (3)	−0.010 (4)
C11	0.063 (3)	0.072 (4)	0.108 (5)	0.005 (3)	0.001 (3)	−0.012 (4)
C12	0.054 (3)	0.061 (3)	0.126 (5)	−0.002 (3)	0.013 (3)	−0.010 (4)
N13	0.045 (2)	0.055 (3)	0.108 (4)	0.007 (2)	0.019 (2)	−0.012 (2)
C14	0.059 (3)	0.072 (4)	0.150 (6)	0.010 (3)	0.041 (4)	−0.018 (4)
C15	0.083 (4)	0.077 (4)	0.109 (5)	0.018 (3)	0.017 (4)	0.003 (4)
C16	0.110 (5)	0.063 (4)	0.088 (4)	−0.012 (4)	0.034 (4)	−0.007 (3)
C17	0.074 (4)	0.081 (4)	0.110 (5)	−0.015 (3)	0.038 (4)	−0.032 (4)
C18	0.058 (3)	0.069 (4)	0.098 (4)	0.004 (3)	0.010 (3)	−0.023 (3)
O19	0.0445 (18)	0.086 (3)	0.083 (2)	−0.0150 (18)	0.0205 (16)	−0.030 (2)

Geometric parameters (Å, º)

N3—C2	1.325 (5)	C11—C12	1.447 (7)
N3—C4	1.351 (5)	C11—H111	0.9700
C4—N5	1.345 (6)	C11—H112	0.9700
C4—N7	1.346 (5)	C12—H121	0.9700
N5—C6	1.320 (5)	C12—H122	0.9700
C6—N13	1.333 (6)	N13—C18	1.459 (6)
N1—C6	1.366 (5)	N13—C14	1.465 (6)
N1—C2	1.394 (6)	C14—C15	1.502 (8)
N1—H1	0.78 (5)	C14—H141	0.9700
C2—O19	1.240 (5)	C14—H142	0.9700
N7—C8	1.465 (6)	C15—C16	1.500 (7)
N7—C12	1.480 (6)	C15—H151	0.9700
C8—C9	1.428 (7)	C15—H152	0.9700
C8—H81	0.9700	C16—C17	1.513 (7)
C8—H82	0.9700	C16—H161	0.9700
C9—C10	1.516 (7)	C16—H162	0.9700
C9—H91	0.9700	C17—C18	1.496 (8)
C9—H92	0.9700	C17—H171	0.9700
C10—C11	1.503 (7)	C17—H172	0.9700
C10—H101	0.9700	C18—H181	0.9700
C10—H102	0.9700	C18—H182	0.9700
C2—N3—C4	116.4 (4)	H111—C11—H112	107.8
N5—C4—N7	116.8 (4)	C11—C12—N7	111.0 (5)
N5—C4—N3	127.1 (4)	C11—C12—H121	109.4
N7—C4—N3	116.1 (5)	N7—C12—H121	109.4
C6—N5—C4	116.1 (4)	C11—C12—H122	109.4
N5—C6—N13	119.7 (4)	N7—C12—H122	109.4
N5—C6—N1	120.3 (5)	H121—C12—H122	108.0
N13—C6—N1	119.9 (4)	C6—N13—C18	121.1 (4)
C6—N1—C2	121.1 (4)	C6—N13—C14	125.5 (4)
C6—N1—H1	123 (4)	C18—N13—C14	113.4 (4)
C2—N1—H1	115 (4)	N13—C14—C15	109.4 (5)
O19—C2—N3	123.9 (5)	N13—C14—H141	109.8
O19—C2—N1	117.1 (4)	C15—C14—H141	109.8
N3—C2—N1	119.0 (4)	N13—C14—H142	109.8
C4—N7—C8	122.8 (4)	C15—C14—H142	109.8
C4—N7—C12	121.9 (4)	H141—C14—H142	108.2
C8—N7—C12	114.2 (4)	C16—C15—C14	111.9 (5)
C9—C8—N7	112.3 (5)	C16—C15—H151	109.2
C9—C8—H81	109.1	C14—C15—H151	109.2
N7—C8—H81	109.1	C16—C15—H152	109.2
C9—C8—H82	109.1	C14—C15—H152	109.2
N7—C8—H82	109.1	H151—C15—H152	107.9
H81—C8—H82	107.9	C15—C16—C17	111.1 (5)
C8—C9—C10	113.1 (5)	C15—C16—H161	109.4
C8—C9—H91	109.0	C17—C16—H161	109.4
C10—C9—H91	109.0	C15—C16—H162	109.4
C8—C9—H92	109.0	C17—C16—H162	109.4
C10—C9—H92	109.0	H161—C16—H162	108.0
H91—C9—H92	107.8	C18—C17—C16	111.1 (5)
C11—C10—C9	109.9 (5)	C18—C17—H171	109.4
C11—C10—H101	109.7	C16—C17—H171	109.4
C9—C10—H101	109.7	C18—C17—H172	109.4
C11—C10—H102	109.7	C16—C17—H172	109.4
C9—C10—H102	109.7	H171—C17—H172	108.0
H101—C10—H102	108.2	N13—C18—C17	111.7 (5)
C12—C11—C10	113.0 (5)	N13—C18—H181	109.3
C12—C11—H111	109.0	C17—C18—H181	109.3
C10—C11—H111	109.0	N13—C18—H182	109.3
C12—C11—H112	109.0	C17—C18—H182	109.3
C10—C11—H112	109.0	H181—C18—H182	107.9
C2—N3—C4—N5	−1.8 (7)	N7—C8—C9—C10	−51.9 (7)
C2—N3—C4—N7	178.1 (5)	C8—C9—C10—C11	52.3 (8)
N7—C4—N5—C6	−179.5 (4)	C9—C10—C11—C12	−53.1 (8)
N3—C4—N5—C6	0.4 (7)	C10—C11—C12—N7	53.2 (7)
C4—N5—C6—N13	−179.2 (4)	C4—N7—C12—C11	139.6 (6)
C4—N5—C6—N1	−0.5 (6)	C8—N7—C12—C11	−52.2 (7)
N5—C6—N1—C2	2.1 (7)	N5—C6—N13—C18	−7.1 (7)
N13—C6—N1—C2	−179.3 (5)	N1—C6—N13—C18	174.2 (5)
C4—N3—C2—O19	−177.0 (5)	N5—C6—N13—C14	171.9 (5)
C4—N3—C2—N1	3.2 (6)	N1—C6—N13—C14	−6.7 (8)
C6—N1—C2—O19	176.7 (4)	C6—N13—C14—C15	−121.7 (6)
C6—N1—C2—N3	−3.5 (7)	C18—N13—C14—C15	57.4 (7)
N5—C4—N7—C8	−170.7 (5)	N13—C14—C15—C16	−55.8 (7)
N3—C4—N7—C8	9.4 (8)	C14—C15—C16—C17	54.2 (7)
N5—C4—N7—C12	−3.5 (7)	C15—C16—C17—C18	−52.0 (7)
N3—C4—N7—C12	176.6 (5)	C6—N13—C18—C17	122.3 (5)
C4—N7—C8—C9	−139.9 (5)	C14—N13—C18—C17	−56.8 (6)
C12—N7—C8—C9	52.0 (7)	C16—C17—C18—N13	52.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O19^i	0.78 (5)	2.04 (5)	2.792 (5)	161 (5)
C14—H142···O19^i	0.97	2.38	3.219 (6)	144

Symmetry code: (i) −x, −y+1, −z.