2,4,6-Tris(dimethyl­amino)-1,3,5-trimethyl­borazine

In the crystal structure of the title compound, C₉H₂₇B₃N₆, the borazine ring displays significant distortion away from a planar six-membered ring to a boat configuration. The distortion results in layered packing of the mol­ecules to accommodate the distorted borazine rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](N-B) = 0.002 Å
• R factor = 0.045
• wR factor = 0.139
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98

   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
   1 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: XSHELL (Bruker, 2000); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,4,6-Tris(dimethylamino)-1,3,5-trimethylborazine

Crystal data

C9H27B3N6	Z = 2
Mr = 251.80	F(000) = 276
Triclinic, P1	Dx = 1.116 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.998 (2) Å	Cell parameters from 100 reflections
b = 10.043 (2) Å	θ = 2.4–25.3°
c = 10.098 (2) Å	µ = 0.07 mm^−1
α = 119.045 (3)°	T = 173 K
β = 100.581 (4)°	Irregular, colorless
γ = 99.473 (3)°	0.39 × 0.35 × 0.31 mm
V = 749.2 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2664 independent reflections
Radiation source: fine-focus sealed tube	2404 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 25.3°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999)	h = −10→10
Tmin = 0.97, Tmax = 0.98	k = −12→12
5393 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0759P)^2 + 0.2627P] where P = (Fo^2 + 2Fc^2)/3
2664 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.15 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
B1	0.2311 (2)	0.6818 (2)	0.0132 (2)	0.0234 (4)
B2	0.2600 (2)	0.8299 (2)	0.3067 (2)	0.0230 (4)
B3	0.2476 (2)	0.9709 (2)	0.1605 (2)	0.0230 (4)
N1	0.28090 (15)	0.70056 (15)	0.16755 (15)	0.0235 (3)
N2	0.23464 (15)	0.96438 (15)	0.29962 (15)	0.0234 (3)
N3	0.20508 (15)	0.81796 (15)	0.00949 (15)	0.0240 (3)
N4	0.21136 (16)	0.53463 (15)	−0.13062 (15)	0.0269 (3)
N5	0.26783 (16)	0.82451 (15)	0.44699 (15)	0.0271 (3)
N6	0.29744 (16)	1.11791 (15)	0.17078 (15)	0.0273 (3)
C1	0.3793 (2)	0.6050 (2)	0.1889 (2)	0.0320 (4)
H1A	0.3113	0.5069	0.1703	0.048*
H1B	0.4522	0.6665	0.2976	0.048*
H1C	0.4401	0.5780	0.1131	0.048*
C2	0.1497 (2)	1.0631 (2)	0.3999 (2)	0.0316 (4)
H2A	0.0776	0.9989	0.4235	0.047*
H2B	0.0889	1.1030	0.3438	0.047*
H2C	0.2259	1.1533	0.4996	0.047*
C3	0.0937 (2)	0.7941 (2)	−0.13168 (19)	0.0327 (4)
H3A	0.1523	0.8065	−0.1997	0.049*
H3B	0.0354	0.8732	−0.0984	0.049*
H3C	0.0189	0.6867	−0.1910	0.049*
C4	0.2469 (2)	0.5267 (2)	−0.26813 (19)	0.0314 (4)
H4A	0.2929	0.6348	−0.2430	0.047*
H4B	0.1494	0.4742	−0.3578	0.047*
H4C	0.3226	0.4656	−0.2966	0.047*
C5	0.1609 (2)	0.37864 (19)	−0.1518 (2)	0.0320 (4)
H5A	0.2505	0.3346	−0.1539	0.048*
H5B	0.0755	0.3073	−0.2523	0.048*
H5C	0.1228	0.3888	−0.0634	0.048*
C6	0.2119 (2)	0.6779 (2)	0.4421 (2)	0.0347 (4)
H6A	0.1587	0.5904	0.3315	0.052*
H6B	0.1373	0.6901	0.5038	0.052*
H6C	0.3019	0.6539	0.4877	0.052*
C7	0.3285 (2)	0.9631 (2)	0.60775 (19)	0.0327 (4)
H7A	0.3827	1.0553	0.6064	0.049*
H7B	0.4031	0.9424	0.6741	0.049*
H7C	0.2405	0.9854	0.6513	0.049*
C8	0.3466 (2)	1.27234 (19)	0.3192 (2)	0.0332 (4)
H8A	0.2594	1.3200	0.3263	0.050*
H8B	0.4384	1.3426	0.3221	0.050*
H8C	0.3750	1.2583	0.4092	0.050*
C9	0.3178 (3)	1.1302 (2)	0.0368 (2)	0.0406 (5)
H9A	0.3302	1.0304	−0.0441	0.061*
H9B	0.4121	1.2184	0.0736	0.061*
H9C	0.2246	1.1501	−0.0091	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0224 (8)	0.0239 (9)	0.0245 (9)	0.0069 (7)	0.0082 (7)	0.0130 (7)
B2	0.0216 (8)	0.0246 (9)	0.0227 (9)	0.0052 (7)	0.0059 (7)	0.0133 (7)
B3	0.0217 (8)	0.0252 (9)	0.0256 (9)	0.0104 (7)	0.0073 (7)	0.0149 (7)
N1	0.0278 (7)	0.0216 (7)	0.0236 (7)	0.0097 (5)	0.0077 (5)	0.0131 (6)
N2	0.0276 (7)	0.0223 (7)	0.0222 (7)	0.0102 (5)	0.0106 (5)	0.0113 (5)
N3	0.0293 (7)	0.0244 (7)	0.0207 (7)	0.0101 (5)	0.0074 (5)	0.0130 (6)
N4	0.0350 (7)	0.0220 (7)	0.0237 (7)	0.0094 (6)	0.0101 (6)	0.0114 (6)
N5	0.0340 (7)	0.0249 (7)	0.0218 (7)	0.0059 (6)	0.0073 (6)	0.0132 (6)
N6	0.0364 (8)	0.0231 (7)	0.0244 (7)	0.0086 (6)	0.0092 (6)	0.0141 (6)
C1	0.0398 (9)	0.0314 (9)	0.0289 (8)	0.0182 (8)	0.0096 (7)	0.0170 (7)
C2	0.0402 (9)	0.0304 (9)	0.0316 (9)	0.0173 (7)	0.0196 (8)	0.0168 (7)
C3	0.0390 (9)	0.0307 (9)	0.0262 (8)	0.0142 (7)	0.0038 (7)	0.0144 (7)
C4	0.0353 (9)	0.0314 (9)	0.0252 (8)	0.0126 (7)	0.0116 (7)	0.0118 (7)
C5	0.0379 (9)	0.0222 (8)	0.0306 (9)	0.0084 (7)	0.0081 (7)	0.0112 (7)
C6	0.0399 (10)	0.0368 (10)	0.0338 (9)	0.0066 (8)	0.0095 (8)	0.0252 (8)
C7	0.0372 (9)	0.0356 (9)	0.0229 (8)	0.0087 (8)	0.0081 (7)	0.0147 (7)
C8	0.0405 (10)	0.0226 (8)	0.0328 (9)	0.0066 (7)	0.0085 (8)	0.0140 (7)
C9	0.0581 (12)	0.0344 (10)	0.0338 (10)	0.0082 (9)	0.0144 (9)	0.0230 (8)

Geometric parameters (Å, º)

B1—N4	1.435 (2)	C2—H2C	0.9800
B1—N3	1.442 (2)	C3—H3A	0.9800
B1—N1	1.448 (2)	C3—H3B	0.9800
B2—N5	1.433 (2)	C3—H3C	0.9800
B2—N2	1.439 (2)	C4—H4A	0.9800
B2—N1	1.450 (2)	C4—H4B	0.9800
B3—N6	1.417 (2)	C4—H4C	0.9800
B3—N2	1.462 (2)	C5—H5A	0.9800
B3—N3	1.466 (2)	C5—H5B	0.9800
N1—C1	1.471 (2)	C5—H5C	0.9800
N2—C2	1.467 (2)	C6—H6A	0.9800
N3—C3	1.469 (2)	C6—H6B	0.9800
N4—C4	1.449 (2)	C6—H6C	0.9800
N4—C5	1.453 (2)	C7—H7A	0.9800
N5—C6	1.449 (2)	C7—H7B	0.9800
N5—C7	1.450 (2)	C7—H7C	0.9800
N6—C8	1.457 (2)	C8—H8A	0.9800
N6—C9	1.458 (2)	C8—H8B	0.9800
C1—H1A	0.9800	C8—H8C	0.9800
C1—H1B	0.9800	C9—H9A	0.9800
C1—H1C	0.9800	C9—H9B	0.9800
C2—H2A	0.9800	C9—H9C	0.9800
C2—H2B	0.9800
N4—B1—N3	121.10 (14)	H3A—C3—H3B	109.5
N4—B1—N1	121.51 (14)	N3—C3—H3C	109.5
N3—B1—N1	117.38 (14)	H3A—C3—H3C	109.5
N5—B2—N2	121.54 (14)	H3B—C3—H3C	109.5
N5—B2—N1	120.85 (14)	N4—C4—H4A	109.5
N2—B2—N1	117.60 (14)	N4—C4—H4B	109.5
N6—B3—N2	121.66 (14)	H4A—C4—H4B	109.5
N6—B3—N3	121.57 (14)	N4—C4—H4C	109.5
N2—B3—N3	116.77 (14)	H4A—C4—H4C	109.5
B1—N1—B2	121.23 (13)	H4B—C4—H4C	109.5
B1—N1—C1	118.96 (13)	N4—C5—H5A	109.5
B2—N1—C1	118.90 (13)	N4—C5—H5B	109.5
B2—N2—B3	118.53 (13)	H5A—C5—H5B	109.5
B2—N2—C2	119.83 (13)	N4—C5—H5C	109.5
B3—N2—C2	118.81 (13)	H5A—C5—H5C	109.5
B1—N3—B3	118.56 (13)	H5B—C5—H5C	109.5
B1—N3—C3	119.72 (13)	N5—C6—H6A	109.5
B3—N3—C3	118.76 (13)	N5—C6—H6B	109.5
B1—N4—C4	123.26 (13)	H6A—C6—H6B	109.5
B1—N4—C5	123.93 (13)	N5—C6—H6C	109.5
C4—N4—C5	112.75 (13)	H6A—C6—H6C	109.5
B2—N5—C6	122.95 (13)	H6B—C6—H6C	109.5
B2—N5—C7	124.42 (14)	N5—C7—H7A	109.5
C6—N5—C7	112.62 (13)	N5—C7—H7B	109.5
B3—N6—C8	123.43 (14)	H7A—C7—H7B	109.5
B3—N6—C9	123.56 (14)	N5—C7—H7C	109.5
C8—N6—C9	112.81 (13)	H7A—C7—H7C	109.5
N1—C1—H1A	109.5	H7B—C7—H7C	109.5
N1—C1—H1B	109.5	N6—C8—H8A	109.5
H1A—C1—H1B	109.5	N6—C8—H8B	109.5
N1—C1—H1C	109.5	H8A—C8—H8B	109.5
H1A—C1—H1C	109.5	N6—C8—H8C	109.5
H1B—C1—H1C	109.5	H8A—C8—H8C	109.5
N2—C2—H2A	109.5	H8B—C8—H8C	109.5
N2—C2—H2B	109.5	N6—C9—H9A	109.5
H2A—C2—H2B	109.5	N6—C9—H9B	109.5
N2—C2—H2C	109.5	H9A—C9—H9B	109.5
H2A—C2—H2C	109.5	N6—C9—H9C	109.5
H2B—C2—H2C	109.5	H9A—C9—H9C	109.5
N3—C3—H3A	109.5	H9B—C9—H9C	109.5
N3—C3—H3B	109.5