1,3,5-Tris(4-meth-oxy-phen-yl)-1,3,5-triazinane-2,4,6-trione.

The complete mol-ecule of the title compound, C24H21N3O6, is generated by the application of threefold rotation symmetry about an axis perpendicular to the central ring. The mol-ecule exhibits a propeller-like shape. The dihedral angle between each benzene ring and the heterocyclic ring is 74.0 (1)°. The mol-ecules pack with no specific inter-molecular inter-actions between them. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] was used to model disordered solvent mol-ecules, presumed to be acetone; the calculated unit-cell data do not take into account the presence of these.

Related literature

For general background to trimerization of aromatic iso­cyanates, see: Raders & Verkade (2010 ▶); Duong et al. (2004 ▶); Tang et al. (1994 ▶); Zhitinkina et al. (1985 ▶); Nawata et al. (1975 ▶); Nicholas & Gmitter (1965 ▶).

Experimental

Crystal data

C24H21N3O6

M = 447.44

Trigonal,

a = 13.2008 (14) Å

c = 26.695 (3) Å

V = 4028.7 (8) Å3

Z = 6

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.51 × 0.49 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.997

6995 measured reflections

1577 independent reflections

1142 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.05

1577 reflections

101 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681303482X/tk5284sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303482X/tk5284Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681303482X/tk5284Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H21N3O6	Dx = 1.107 Mg m−3
Mr = 447.44	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c	Cell parameters from 1247 reflections
Hall symbol: R 3 -2"c	θ = 2.3–20.4°
a = 13.2008 (14) Å	µ = 0.08 mm−1
c = 26.695 (3) Å	T = 200 K
V = 4028.7 (8) Å3	Block, colourless
Z = 6	0.51 × 0.49 × 0.04 mm
F(000) = 1404

Bruker SMART CCD area-detector diffractometer	1577 independent reflections
Radiation source: fine-focus sealed tube	1142 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
phi and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→15
Tmin = 0.960, Tmax = 0.997	k = −15→14
6995 measured reflections	l = −31→31

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3
1577 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.12 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.24317 (15)	0.68853 (16)	0.06336 (8)	0.0507 (6)
O1	0.37628 (17)	0.88360 (16)	0.06161 (9)	0.0710 (6)
O2	−0.1275 (2)	0.7774 (3)	0.06263 (12)	0.1146 (9)
C1	0.1470 (2)	0.7108 (2)	0.06541 (11)	0.0552 (7)
C2	0.0864 (2)	0.6942 (2)	0.10907 (12)	0.0652 (7)
H2	0.1090	0.6709	0.1387	0.078*
C3	−0.0104 (3)	0.7124 (3)	0.10944 (13)	0.0768 (9)
H3	−0.0565	0.6970	0.1388	0.092*
C4	−0.0369 (2)	0.7525 (3)	0.06691 (14)	0.0724 (8)
C5	0.0253 (3)	0.7708 (3)	0.02514 (15)	0.0878 (10)
H5	0.0050	0.7983	−0.0039	0.105*
C6	0.1168 (3)	0.7514 (3)	0.02308 (12)	0.0729 (8)
H6	0.1600	0.7654	−0.0071	0.088*
C7	0.3566 (2)	0.7838 (2)	0.06225 (11)	0.0566 (7)
C8	−0.2060 (4)	0.7446 (5)	0.1028 (2)	0.1312 (17)
H8A	−0.2414	0.6604	0.1087	0.197*
H8B	−0.2674	0.7631	0.0948	0.197*
H8C	−0.1641	0.7874	0.1329	0.197*

	U11	U22	U33	U12	U13	U23
N1	0.0390 (12)	0.0406 (12)	0.0734 (15)	0.0206 (10)	0.0029 (11)	0.0033 (11)
O1	0.0571 (12)	0.0488 (12)	0.1124 (15)	0.0306 (10)	−0.0006 (11)	−0.0036 (10)
O2	0.0943 (19)	0.158 (3)	0.127 (2)	0.0896 (19)	0.0056 (17)	0.0234 (18)
C1	0.0452 (16)	0.0456 (15)	0.0770 (18)	0.0242 (14)	0.0011 (15)	−0.0026 (14)
C2	0.0608 (17)	0.0636 (18)	0.0762 (19)	0.0350 (14)	0.0076 (14)	0.0051 (15)
C3	0.0591 (18)	0.080 (2)	0.089 (2)	0.0331 (16)	0.0207 (15)	0.0075 (17)
C4	0.0538 (16)	0.078 (2)	0.098 (2)	0.0429 (16)	−0.0027 (18)	0.0036 (17)
C5	0.071 (2)	0.111 (3)	0.093 (3)	0.054 (2)	−0.008 (2)	0.0187 (19)
C6	0.0654 (19)	0.079 (2)	0.081 (2)	0.0410 (16)	0.0038 (16)	0.0179 (16)
C7	0.0465 (16)	0.0472 (16)	0.0751 (19)	0.0227 (11)	0.0012 (14)	−0.0021 (14)
C8	0.085 (3)	0.174 (4)	0.166 (4)	0.088 (3)	0.016 (3)	−0.011 (4)

N1—C7i	1.384 (3)	C3—C4	1.370 (5)
N1—C7	1.393 (3)	C3—H3	0.9500
N1—C1	1.440 (3)	C4—C5	1.333 (4)
O1—C7	1.209 (3)	C5—C6	1.356 (4)
O2—C4	1.395 (4)	C5—H5	0.9500
O2—C8	1.400 (5)	C6—H6	0.9500
C1—C2	1.368 (4)	C7—N1ii	1.384 (3)
C1—C6	1.392 (4)	C8—H8A	0.9800
C2—C3	1.413 (4)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C7i—N1—C7	124.2 (3)	C4—C5—C6	121.7 (3)
C7i—N1—C1	117.35 (19)	C4—C5—H5	119.2
C7—N1—C1	118.43 (19)	C6—C5—H5	119.2
C4—O2—C8	117.0 (3)	C5—C6—C1	119.6 (3)
C2—C1—C6	119.7 (2)	C5—C6—H6	120.2
C2—C1—N1	120.3 (3)	C1—C6—H6	120.2
C6—C1—N1	120.0 (2)	O1—C7—N1ii	122.2 (2)
C1—C2—C3	119.1 (3)	O1—C7—N1	122.1 (2)
C1—C2—H2	120.5	N1ii—C7—N1	115.7 (3)
C3—C2—H2	120.5	O2—C8—H8A	109.5
C4—C3—C2	119.1 (3)	O2—C8—H8B	109.5
C4—C3—H3	120.4	H8A—C8—H8B	109.5
C2—C3—H3	120.4	O2—C8—H8C	109.5
C5—C4—C3	120.7 (3)	H8A—C8—H8C	109.5
C5—C4—O2	114.3 (3)	H8B—C8—H8C	109.5
C3—C4—O2	125.0 (3)