1,3,5-Tris(4-chloro­phen­yl)-1,3,5-triazinane-2,4,6-trione acetone solvate

In the title compound, C₂₁H₁₂Cl₃N₃O₃·C₄H₉O, the six-membered heterocyclic ring lies on a threefold rotation axis and adopts a planar conformation. The mol­ecule exhibits a propeller-like shape. The acetone solvent mol­ecule is disordered.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.049
• wR factor = 0.112
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         C9
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      38.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.36 Ratio

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               1261
           Count of symmetry unique reflns          916
           Completeness (_total/calc)            137.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       345
           Fraction of Friedel pairs measured     0.377
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

1,3,5-Tris(4-chlorophenyl)-1,3,5-triazinane-2,4,6-trione acetone solvate

Crystal data

C21H12Cl3N3O3·C4H9O	Dx = 1.422 Mg m^−3
Mr = 533.80	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3c	Cell parameters from 2224 reflections
Hall symbol: R 3 -2"c	θ = 2.3–22.5°
a = 12.7911 (9) Å	µ = 0.41 mm^−1
c = 26.403 (4) Å	T = 292 K
V = 3741.1 (6) Å^3	Block, colourless
Z = 6	0.30 × 0.20 × 0.10 mm
F(000) = 1650

Data collection

Bruker SMART CCD area-detector diffractometer	966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 27.0°, θmin = 3.6°
φ and ω scans	h = −15→16
4820 measured reflections	k = −16→16
1261 independent reflections	l = −19→33

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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0512P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
1261 reflections	Δρmax = 0.16 e Å^−3
112 parameters	Δρmin = −0.16 e Å^−3
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (11)

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	Occ. (<1)
C1	0.9859 (3)	1.1031 (3)	0.98324 (12)	0.0472 (6)
C2	0.7677 (3)	0.9712 (3)	0.97957 (12)	0.0479 (7)
C3	0.7272 (3)	0.9857 (3)	0.93385 (12)	0.0552 (8)
H3	0.7768	1.0062	0.9055	0.062 (9)*
C4	0.6126 (4)	0.9700 (4)	0.92961 (13)	0.0651 (9)
H4	0.5854	0.9828	0.8988	0.055 (9)*
C5	0.5404 (3)	0.9356 (4)	0.97124 (16)	0.0666 (10)
C6	0.5808 (4)	0.9210 (5)	1.01771 (13)	0.0728 (11)
H6	0.5304	0.8986	1.0459	0.089 (13)*
C7	0.6962 (3)	0.9401 (4)	1.02202 (12)	0.0604 (9)
H7	0.7253	0.9320	1.0532	0.053 (9)*
C8	0.740 (2)	0.294 (3)	0.9989 (6)	0.197 (10)*	0.70 (4)
H8A	0.7718	0.2553	0.9779	0.295*	0.70 (4)
H8B	0.6890	0.2393	1.0245	0.295*	0.70 (4)
H8C	0.8055	0.3641	1.0146	0.295*	0.70 (4)
C8'	0.634 (6)	0.221 (3)	0.9966 (16)	0.21 (2)*	0.30 (4)
H8E	0.6926	0.1962	0.9907	0.308*	0.30 (4)
H8F	0.5556	0.1570	0.9864	0.308*	0.30 (4)
H8D	0.6323	0.2370	1.0320	0.308*	0.30 (4)
C9	0.6667	0.3333	0.9663 (4)	0.118 (4)
Cl1	0.39437 (12)	0.9114 (2)	0.96640 (5)	0.1199 (7)
N1	0.8886 (2)	0.9865 (2)	0.98283 (9)	0.0466 (6)
O1	0.9734 (2)	1.1898 (2)	0.98321 (9)	0.0641 (7)
O2	0.6667	0.3333	0.9215 (3)	0.230 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0438 (18)	0.0450 (17)	0.0569 (16)	0.0253 (15)	0.0028 (13)	0.0027 (13)
C2	0.0385 (16)	0.0457 (17)	0.0592 (18)	0.0209 (14)	0.0019 (12)	0.0035 (13)
C3	0.0535 (19)	0.064 (2)	0.0508 (17)	0.0311 (18)	0.0080 (14)	0.0080 (14)
C4	0.058 (2)	0.087 (3)	0.0571 (19)	0.042 (2)	−0.0070 (16)	0.0078 (17)
C5	0.051 (2)	0.099 (3)	0.0634 (19)	0.048 (2)	0.0035 (16)	0.0112 (18)
C6	0.055 (2)	0.111 (3)	0.060 (2)	0.047 (2)	0.0126 (16)	0.016 (2)
C7	0.058 (2)	0.084 (3)	0.0492 (17)	0.043 (2)	−0.0008 (14)	0.0057 (15)
C9	0.140 (6)	0.140 (6)	0.072 (5)	0.070 (3)	0.000	0.000
Cl1	0.0724 (8)	0.227 (2)	0.0895 (8)	0.0965 (10)	0.0048 (5)	0.0206 (8)
N1	0.0365 (13)	0.0384 (15)	0.0625 (14)	0.0168 (12)	0.0023 (11)	0.0030 (11)
O1	0.0538 (15)	0.0472 (14)	0.095 (2)	0.0281 (11)	0.0056 (12)	0.0014 (11)
O2	0.309 (11)	0.309 (11)	0.071 (6)	0.155 (5)	0.000	0.000

Geometric parameters (Å, º)

C1—O1	1.198 (4)	C8—C9	1.529 (9)
C1—N1^i	1.383 (4)	C8—H8A	0.9600
C1—N1	1.385 (4)	C8—H8B	0.9600
C2—C3	1.362 (4)	C8—H8C	0.9600
C2—C7	1.374 (5)	C8'—C9	1.515 (9)
C2—N1	1.461 (4)	C8'—H8E	0.9600
C3—C4	1.381 (5)	C8'—H8F	0.9600
C3—H3	0.9300	C8'—H8D	0.9600
C4—C5	1.360 (6)	C9—O2	1.181 (13)
C4—H4	0.9300	C9—C8'^ii	1.514 (9)
C5—C6	1.379 (6)	C9—C8'^iii	1.514 (9)
C5—Cl1	1.739 (3)	C9—C8^iii	1.529 (9)
C6—C7	1.375 (5)	C9—C8^ii	1.529 (9)
C6—H6	0.9300	N1—C1^iv	1.383 (4)
C7—H7	0.9300
O1—C1—N1^i	122.8 (3)	C9—C8'—H8D	109.5
O1—C1—N1	122.2 (3)	H8E—C8'—H8D	109.5
N1^i—C1—N1	115.0 (3)	H8F—C8'—H8D	109.5
C3—C2—C7	121.3 (3)	O2—C9—C8'^ii	122 (2)
C3—C2—N1	118.9 (3)	O2—C9—C8'^iii	122.0 (19)
C7—C2—N1	119.8 (3)	C8'^ii—C9—C8'^iii	95 (3)
C2—C3—C4	120.0 (3)	O2—C9—C8'	122.0 (19)
C2—C3—H3	120.0	C8'^ii—C9—C8'	95 (3)
C4—C3—H3	120.0	C8'^iii—C9—C8'	95 (3)
C5—C4—C3	118.8 (3)	O2—C9—C8^iii	124.2 (8)
C5—C4—H4	120.6	C8'^ii—C9—C8^iii	114 (2)
C3—C4—H4	120.6	C8'^iii—C9—C8^iii	46.8 (19)
C4—C5—C6	121.6 (3)	C8'—C9—C8^iii	52.3 (18)
C4—C5—Cl1	119.6 (3)	O2—C9—C8^ii	124.2 (8)
C6—C5—Cl1	118.9 (3)	C8'^ii—C9—C8^ii	46.8 (19)
C7—C6—C5	119.4 (3)	C8'^iii—C9—C8^ii	52.3 (18)
C7—C6—H6	120.3	C8'—C9—C8^ii	114 (2)
C5—C6—H6	120.3	C8^iii—C9—C8^ii	91.4 (11)
C2—C7—C6	118.9 (3)	O2—C9—C8	124.2 (8)
C2—C7—H7	120.5	C8'^ii—C9—C8	52.3 (18)
C6—C7—H7	120.5	C8'^iii—C9—C8	114 (2)
C9—C8—H8A	109.5	C8'—C9—C8	46.8 (19)
C9—C8—H8B	109.5	C8^iii—C9—C8	91.4 (11)
C9—C8—H8C	109.5	C8^ii—C9—C8	91.4 (11)
C9—C8'—H8E	109.5	C1^iv—N1—C1	125.0 (3)
C9—C8'—H8F	109.5	C1^iv—N1—C2	117.1 (2)
H8E—C8'—H8F	109.5	C1—N1—C2	117.8 (3)

Symmetry codes: (i) −x+y+1, −x+2, z; (ii) −y+1, x−y, z; (iii) −x+y+1, −x+1, z; (iv) −y+2, x−y+1, z.