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.
Supporting information
CCDC reference: 221706
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colorless |
Z = 4 | 0.45 × 0.43 × 0.34 mm |
F(000) = 1152 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0405P)2 + 1.0368P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (6) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
N1—C2 | 1.452 (2) | N3—S3 | 1.6506 (17) |
N1—C2i | 1.452 (2) | S3—O3B | 1.4228 (16) |
N1—S1 | 1.670 (3) | S3—O3A | 1.4262 (15) |
S1—O1Ai | 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—C12i | 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—C13i | 1.369 (3) | C35—H35 | 0.9300 |
C2—N3 | 1.481 (2) | C36—H36 | 0.9300 |
C2—H2A | 0.9700 | C4—N3i | 1.461 (2) |
C2—H2B | 0.9700 | C4—H4A | 0.9700 |
N3—C4 | 1.461 (2) | C4—H4B | 0.9700 |
| | | |
C2—N1—C2i | 112.3 (2) | O3B—S3—O3A | 120.65 (10) |
C2—N1—S1 | 118.56 (13) | O3B—S3—N3 | 105.80 (9) |
C2i—N1—S1 | 118.56 (13) | O3A—S3—N3 | 105.99 (9) |
O1Ai—S1—O1A | 121.26 (15) | O3B—S3—C31 | 109.55 (10) |
O1Ai—S1—N1 | 104.49 (9) | O3A—S3—C31 | 108.49 (10) |
O1A—S1—N1 | 104.49 (9) | N3—S3—C31 | 105.24 (9) |
O1Ai—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—C12i | 120.9 (3) | C33—C32—C31 | 119.3 (2) |
C12—C11—S1 | 119.49 (14) | C33—C32—H32 | 120.4 |
C12i—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—C13i | 118.45 (15) | C34—C35—C36 | 118.4 (2) |
F1—C14—C13 | 118.45 (15) | C34—C35—H35 | 120.8 |
C13i—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 | N3i—C4—N3 | 107.9 (2) |
N3—C2—H2B | 109.8 | N3i—C4—H4A | 110.1 |
H2A—C2—H2B | 108.2 | N3—C4—H4A | 110.1 |
C4—N3—C2 | 111.49 (18) | N3i—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—N3i | 59.3 (3) | C2—N3—S3—C31 | 70.41 (16) |
N3—C4—N3i—C2i | −59.3 (3) | C4—N3—S3—C31 | −62.00 (18) |
C4—N3i—C2i—N1 | 58.0 (2) | | |
Symmetry code: (i) x, −y+1/2, z. |
Comparison of torsion angles (°) in the 1,3,5-triazacyclohexane
ring in the CSD with those (I) topTorsion | Averagea | Minimum | Maximum | (I) |
N1—C2—N3—C4 | -57.193 | -62.495 | -42.857 | -58.0 (2) |
C2—N3—C4—N5 | 57.499 | 45.484 | 64.052 | 59.3 (3) |
N3—C4—N5—C6 | -56.289 | -62.231 | -46.254 | -59.3 (3) |
C4—N5—C6—N1 | 55.063 | 44.809 | 61.292 | -58.0 (2) |
N5—C6—N1—C2 | -55.192 | -61.488 | -42.518 | -59.3 (3) |
C6—N1—C2—N3 | 55.871 | 41.295 | 60.660 | 59.3 (3) |
Notes: (a) CSD (Version 5.24 of November 2002; Allen, 2002). |