1,3,5-Tris(4-fluoro­benzene­sulfonyl)-1,3,5-tri­aza­cyclo­hexane

The title compound, C₂₁H₁₈F₃N₃O₆S₃, has a chair conformation that is similar to the majority of the 1,3,5-tri­aza­cyclo­hexane rings reported in the literature. It is the product of a condensation reaction between fluoro­benzene­sulfon­amide and form­aldehyde, and its empirical and structural formula were determined by X-ray analysis. The mol­ecules are located on mirror planes in space group Pnma.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.096
• Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,3,5-tris(4-fluorobensenesulfonyl)-1,3,5-triazacyclohexane

Crystal data

C21H18F3N3O6S3	Dx = 1.591 Mg m^−3
Mr = 561.56	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 66 reflections
a = 12.2603 (12) Å	θ = 10.0–13.5°
b = 16.4739 (13) Å	µ = 0.39 mm^−1
c = 11.6085 (6) Å	T = 293 K
V = 2344.6 (3) Å^3	Block, colorless
Z = 4	0.45 × 0.43 × 0.34 mm
F(000) = 1152

Data collection

Bruker P4 diffractometer	1942 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 26.0°, θmin = 2.2°
2θ/ω scans	h = −1→15
Absorption correction: integration (Wuensch & Prewitt, 1965)	k = −20→8
Tmin = 0.855, Tmax = 0.893	l = −1→14
2707 measured reflections	3 standard reflections every 97 reflections
2390 independent reflections	intensity decay: 0.0%

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 1.0368P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2390 reflections	Δρmax = 0.41 e Å^−3
173 parameters	Δρmin = −0.31 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: 0.0043 (6)

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
N1	0.76747 (19)	0.2500	0.0933 (2)	0.0366 (6)
S1	0.76894 (6)	0.2500	−0.05061 (7)	0.0406 (2)
O1A	0.72028 (13)	0.32531 (11)	−0.08186 (14)	0.0557 (5)
C11	0.9057 (2)	0.2500	−0.0955 (2)	0.0362 (7)
C12	0.95990 (19)	0.32300 (14)	−0.10891 (19)	0.0439 (5)
H12	0.9223	0.3718	−0.1017	0.053*
C13	1.0698 (2)	0.32304 (14)	−0.1330 (2)	0.0488 (6)
H13	1.1076	0.3715	−0.1425	0.059*
C14	1.1222 (3)	0.2500	−0.1428 (3)	0.0473 (8)
F1	1.23089 (16)	0.2500	−0.1620 (2)	0.0717 (7)
C2	0.80070 (16)	0.32319 (13)	0.15346 (19)	0.0378 (5)
H2A	0.7637	0.3264	0.2272	0.045*
H2B	0.7808	0.3706	0.1085	0.045*
N3	0.92022 (13)	0.32171 (10)	0.17156 (14)	0.0329 (4)
S3	0.97596 (4)	0.40764 (3)	0.21495 (5)	0.03618 (17)
O3A	1.09081 (11)	0.39392 (10)	0.21603 (15)	0.0472 (4)
O3B	0.92995 (14)	0.46931 (10)	0.14423 (14)	0.0501 (4)
C31	0.93145 (17)	0.42054 (12)	0.35776 (19)	0.0356 (5)
C32	0.99331 (18)	0.38818 (14)	0.4467 (2)	0.0441 (5)
H32	1.0603	0.3640	0.4314	0.053*
C33	0.9546 (2)	0.39232 (15)	0.5577 (2)	0.0493 (6)
H33	0.9950	0.3715	0.6187	0.059*
C34	0.8552 (2)	0.42777 (15)	0.5763 (2)	0.0488 (6)
F3	0.81735 (14)	0.43195 (11)	0.68598 (13)	0.0720 (5)
C35	0.79260 (19)	0.46008 (15)	0.4901 (2)	0.0492 (6)
H35	0.7256	0.4840	0.5063	0.059*
C36	0.83109 (17)	0.45631 (14)	0.3793 (2)	0.0427 (5)
H36	0.7902	0.4776	0.3189	0.051*
C4	0.9539 (2)	0.2500	0.2365 (3)	0.0337 (6)
H4A	1.0324	0.2500	0.2468	0.040*
H4B	0.9198	0.2500	0.3119	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0261 (12)	0.0472 (15)	0.0364 (13)	0.000	−0.0024 (10)	0.000
S1	0.0281 (4)	0.0561 (5)	0.0377 (4)	0.000	−0.0042 (3)	0.000
O1A	0.0435 (9)	0.0757 (12)	0.0480 (9)	0.0179 (9)	−0.0049 (8)	0.0107 (9)
C11	0.0321 (15)	0.0435 (17)	0.0331 (15)	0.000	0.0010 (12)	0.000
C12	0.0438 (12)	0.0397 (12)	0.0482 (13)	0.0045 (10)	0.0043 (10)	0.0040 (10)
C13	0.0478 (13)	0.0445 (14)	0.0542 (14)	−0.0103 (11)	0.0068 (11)	0.0050 (11)
C14	0.0341 (16)	0.060 (2)	0.0481 (19)	0.000	0.0079 (14)	0.000
F1	0.0368 (11)	0.0877 (17)	0.0905 (17)	0.000	0.0144 (11)	0.000
C2	0.0253 (10)	0.0466 (13)	0.0415 (11)	0.0064 (9)	−0.0025 (8)	−0.0024 (10)
N3	0.0243 (8)	0.0370 (10)	0.0374 (9)	0.0027 (7)	−0.0024 (7)	0.0001 (7)
S3	0.0290 (3)	0.0341 (3)	0.0455 (3)	−0.0004 (2)	0.0005 (2)	0.0034 (2)
O3A	0.0277 (7)	0.0485 (9)	0.0655 (11)	−0.0041 (7)	0.0044 (7)	0.0019 (8)
O3B	0.0523 (10)	0.0409 (9)	0.0571 (10)	0.0028 (8)	−0.0008 (8)	0.0133 (8)
C31	0.0301 (10)	0.0324 (11)	0.0444 (11)	0.0005 (8)	−0.0042 (9)	−0.0041 (9)
C32	0.0343 (11)	0.0449 (12)	0.0531 (14)	0.0053 (10)	−0.0076 (10)	−0.0054 (11)
C33	0.0525 (14)	0.0514 (14)	0.0441 (13)	0.0043 (12)	−0.0125 (11)	−0.0047 (11)
C34	0.0539 (14)	0.0484 (13)	0.0441 (13)	−0.0055 (11)	0.0031 (11)	−0.0142 (11)
F3	0.0812 (12)	0.0852 (12)	0.0496 (9)	0.0033 (9)	0.0109 (8)	−0.0173 (8)
C35	0.0396 (12)	0.0487 (14)	0.0593 (15)	0.0054 (11)	0.0035 (11)	−0.0139 (12)
C36	0.0342 (11)	0.0408 (12)	0.0531 (13)	0.0054 (10)	−0.0047 (10)	−0.0054 (11)
C4	0.0287 (14)	0.0342 (15)	0.0382 (15)	0.000	−0.0038 (12)	0.000

Geometric parameters (Å, º)

N1—C2	1.452 (2)	N3—S3	1.6506 (17)
N1—C2^i	1.452 (2)	S3—O3B	1.4228 (16)
N1—S1	1.670 (3)	S3—O3A	1.4262 (15)
S1—O1A^i	1.4237 (17)	S3—C31	1.758 (2)
S1—O1A	1.4237 (17)	C31—C36	1.387 (3)
S1—C11	1.756 (3)	C31—C32	1.388 (3)
C11—C12	1.383 (3)	C32—C33	1.374 (3)
C11—C12^i	1.383 (3)	C32—H32	0.9300
C12—C13	1.376 (3)	C33—C34	1.368 (3)
C12—H12	0.9300	C33—H33	0.9300
C13—C14	1.369 (3)	C34—F3	1.357 (3)
C13—H13	0.9300	C34—C35	1.369 (4)
C14—F1	1.351 (4)	C35—C36	1.372 (3)
C14—C13^i	1.369 (3)	C35—H35	0.9300
C2—N3	1.481 (2)	C36—H36	0.9300
C2—H2A	0.9700	C4—N3^i	1.461 (2)
C2—H2B	0.9700	C4—H4A	0.9700
N3—C4	1.461 (2)	C4—H4B	0.9700
C2—N1—C2^i	112.3 (2)	O3B—S3—O3A	120.65 (10)
C2—N1—S1	118.56 (13)	O3B—S3—N3	105.80 (9)
C2^i—N1—S1	118.56 (13)	O3A—S3—N3	105.99 (9)
O1A^i—S1—O1A	121.26 (15)	O3B—S3—C31	109.55 (10)
O1A^i—S1—N1	104.49 (9)	O3A—S3—C31	108.49 (10)
O1A—S1—N1	104.49 (9)	N3—S3—C31	105.24 (9)
O1A^i—S1—C11	108.95 (8)	C36—C31—C32	120.9 (2)
O1A—S1—C11	108.95 (8)	C36—C31—S3	119.76 (17)
N1—S1—C11	107.86 (13)	C32—C31—S3	119.06 (16)
C12—C11—C12^i	120.9 (3)	C33—C32—C31	119.3 (2)
C12—C11—S1	119.49 (14)	C33—C32—H32	120.4
C12^i—C11—S1	119.49 (14)	C31—C32—H32	120.4
C13—C12—C11	119.6 (2)	C34—C33—C32	118.5 (2)
C13—C12—H12	120.2	C34—C33—H33	120.7
C11—C12—H12	120.2	C32—C33—H33	120.7
C14—C13—C12	118.4 (2)	F3—C34—C33	118.3 (2)
C14—C13—H13	120.8	F3—C34—C35	118.3 (2)
C12—C13—H13	120.8	C33—C34—C35	123.3 (2)
F1—C14—C13^i	118.45 (15)	C34—C35—C36	118.4 (2)
F1—C14—C13	118.45 (15)	C34—C35—H35	120.8
C13^i—C14—C13	123.1 (3)	C36—C35—H35	120.8
N1—C2—N3	109.41 (17)	C35—C36—C31	119.6 (2)
N1—C2—H2A	109.8	C35—C36—H36	120.2
N3—C2—H2A	109.8	C31—C36—H36	120.2
N1—C2—H2B	109.8	N3^i—C4—N3	107.9 (2)
N3—C2—H2B	109.8	N3^i—C4—H4A	110.1
H2A—C2—H2B	108.2	N3—C4—H4A	110.1
C4—N3—C2	111.49 (18)	N3^i—C4—H4B	110.1
C4—N3—S3	114.78 (13)	N3—C4—H4B	110.1
C2—N3—S3	116.03 (13)	H4A—C4—H4B	108.4
N1—C2—N3—C4	−58.0 (2)	C2—N1—S1—C11	71.01 (16)
C2—N3—C4—N3^i	59.3 (3)	C2—N3—S3—C31	70.41 (16)
N3—C4—N3^i—C2^i	−59.3 (3)	C4—N3—S3—C31	−62.00 (18)
C4—N3^i—C2^i—N1	58.0 (2)

Symmetry code: (i) x, −y+1/2, z.