Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017021/ob6275sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017021/ob6275Isup2.hkl |
CCDC reference: 222857
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.124
- Data-to-parameter ratio = 10.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.11 From the CIF: _reflns_number_total 3177 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3369 Completeness (_total/calc) 94.30% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Potassium carbonate (0.1 g, 0.27 mmol) and methallyl dichloride (0.038 g, 0.30 mmol) were added to a solution of methylene bis(4-fluorobenzenesulfonamide) (0.1 g, 0.27 mmol) in acetonitrile. The reaction mixture was heated at reflux overnight and then the resulting mixture was cooled to room temperature, filtered and concentrated to obtain a crystalline residue, which was recrystallized from a mixture of absolute ethanol and dried to obtain (1) as colorless crystals with a melting point of 457–458 K.
All of the H atoms were refined freely. The C—H bond distances are 0.86 (4)–1.03 (3) Å.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C17H16F2N2O4S2 | F(000) = 856 |
Mr = 414.44 | Dx = 1.455 Mg m−3 |
Monoclinic, P21/n | Melting point = 457–458 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54178 Å |
a = 13.8591 (2) Å | Cell parameters from 7044 reflections |
b = 10.8218 (1) Å | θ = 3.8–67.0° |
c = 13.8946 (2) Å | µ = 2.97 mm−1 |
β = 114.751 (1)° | T = 294 K |
V = 1892.48 (5) Å3 | Plate, colorless |
Z = 4 | 0.18 × 0.16 × 0.05 mm |
Bruker SMART CCD area-detector diffractometer | 3177 independent reflections |
Radiation source: fine-focus sealed tube | 2783 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ϕ and ω scans | θmax = 67.1°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→16 |
Tmin = 0.686, Tmax = 0.862 | k = −11→12 |
9044 measured reflections | l = −15→15 |
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)] = 0.045 | All H-atom parameters refined |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0828P)2 + 0.1403P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3177 reflections | Δρmax = 0.24 e Å−3 |
309 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0116 (7) |
C17H16F2N2O4S2 | V = 1892.48 (5) Å3 |
Mr = 414.44 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 13.8591 (2) Å | µ = 2.97 mm−1 |
b = 10.8218 (1) Å | T = 294 K |
c = 13.8946 (2) Å | 0.18 × 0.16 × 0.05 mm |
β = 114.751 (1)° |
Bruker SMART CCD area-detector diffractometer | 3177 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2783 reflections with I > 2σ(I) |
Tmin = 0.686, Tmax = 0.862 | Rint = 0.032 |
9044 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.24 e Å−3 |
3177 reflections | Δρmin = −0.35 e Å−3 |
309 parameters |
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 | ||
S1 | 0.38019 (4) | 0.57707 (4) | 0.10099 (4) | 0.0575 (2) | |
S2 | 0.66270 (4) | 0.83976 (5) | 0.14058 (4) | 0.0642 (2) | |
O1B | 0.38055 (12) | 0.56931 (15) | −0.00144 (12) | 0.0697 (4) | |
N1 | 0.50458 (13) | 0.56938 (15) | 0.18668 (13) | 0.0564 (4) | |
O2B | 0.59433 (12) | 0.83484 (16) | 0.02996 (12) | 0.0767 (5) | |
O1A | 0.32549 (13) | 0.48619 (14) | 0.13395 (13) | 0.0748 (4) | |
N3 | 0.60807 (13) | 0.75132 (15) | 0.19882 (13) | 0.0575 (4) | |
C15 | 0.2208 (2) | 0.8453 (3) | 0.1708 (2) | 0.0831 (7) | |
C14 | 0.2440 (2) | 0.9444 (2) | 0.1244 (2) | 0.0783 (7) | |
C2 | 0.58612 (16) | 0.62316 (19) | 0.15980 (18) | 0.0576 (5) | |
O2A | 0.68482 (14) | 0.95557 (16) | 0.19455 (15) | 0.0869 (5) | |
C6 | 0.5301 (2) | 0.5748 (2) | 0.30056 (19) | 0.0691 (6) | |
C11 | 0.32773 (15) | 0.72206 (19) | 0.11110 (15) | 0.0555 (5) | |
F14 | 0.20086 (17) | 1.05554 (16) | 0.12776 (15) | 0.1136 (6) | |
F24 | 1.05857 (14) | 0.5984 (2) | 0.1956 (2) | 0.1407 (9) | |
C21 | 0.78362 (16) | 0.7691 (2) | 0.15712 (17) | 0.0633 (5) | |
C12 | 0.35262 (17) | 0.8246 (2) | 0.06658 (17) | 0.0612 (5) | |
C16 | 0.26276 (19) | 0.7321 (3) | 0.1640 (2) | 0.0709 (6) | |
C22 | 0.7887 (2) | 0.7031 (3) | 0.0756 (2) | 0.0753 (6) | |
C13 | 0.3096 (2) | 0.9379 (2) | 0.07304 (19) | 0.0726 (6) | |
C26 | 0.87125 (19) | 0.7789 (3) | 0.2547 (2) | 0.0773 (7) | |
C5 | 0.56452 (18) | 0.7019 (2) | 0.34479 (16) | 0.0702 (6) | |
C4 | 0.6470 (2) | 0.7585 (3) | 0.31561 (18) | 0.0744 (6) | |
C25 | 0.9646 (2) | 0.7199 (3) | 0.2675 (3) | 0.0917 (9) | |
C23 | 0.8814 (2) | 0.6455 (3) | 0.0879 (3) | 0.0934 (8) | |
C24 | 0.9669 (2) | 0.6562 (3) | 0.1841 (3) | 0.0946 (9) | |
C5A | 0.5268 (3) | 0.7570 (4) | 0.4059 (3) | 0.1002 (10) | |
H4A | 0.713 (2) | 0.710 (3) | 0.348 (2) | 0.087 (8)* | |
H12 | 0.397 (2) | 0.819 (2) | 0.0300 (19) | 0.076 (7)* | |
H2A | 0.5646 (16) | 0.622 (2) | 0.0857 (18) | 0.058 (6)* | |
H4B | 0.662 (2) | 0.847 (3) | 0.342 (2) | 0.098 (9)* | |
H6A | 0.593 (2) | 0.516 (3) | 0.339 (2) | 0.092 (8)* | |
H16 | 0.248 (2) | 0.664 (3) | 0.194 (2) | 0.082 (8)* | |
H22 | 0.733 (2) | 0.699 (2) | 0.013 (2) | 0.078 (7)* | |
H6B | 0.468 (2) | 0.551 (3) | 0.304 (2) | 0.081 (8)* | |
H2B | 0.648 (2) | 0.574 (2) | 0.194 (2) | 0.077 (7)* | |
H5A | 0.476 (3) | 0.729 (3) | 0.420 (3) | 0.116 (12)* | |
H25 | 1.024 (3) | 0.726 (3) | 0.327 (3) | 0.104 (10)* | |
H5B | 0.551 (2) | 0.839 (3) | 0.428 (2) | 0.092 (9)* | |
H13 | 0.324 (2) | 1.006 (3) | 0.049 (2) | 0.083 (8)* | |
H26 | 0.865 (2) | 0.826 (3) | 0.312 (2) | 0.087 (8)* | |
H23 | 0.888 (3) | 0.593 (4) | 0.033 (3) | 0.128 (13)* | |
H15 | 0.177 (3) | 0.858 (3) | 0.211 (2) | 0.104 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0571 (3) | 0.0574 (3) | 0.0572 (3) | −0.00605 (19) | 0.0233 (2) | −0.00788 (19) |
S2 | 0.0603 (3) | 0.0622 (3) | 0.0608 (4) | −0.0069 (2) | 0.0163 (2) | 0.0040 (2) |
O1B | 0.0724 (9) | 0.0808 (10) | 0.0540 (9) | −0.0029 (7) | 0.0245 (7) | −0.0171 (7) |
N1 | 0.0596 (9) | 0.0554 (9) | 0.0539 (10) | −0.0002 (7) | 0.0237 (8) | 0.0002 (6) |
O2B | 0.0659 (9) | 0.0918 (12) | 0.0600 (10) | −0.0024 (8) | 0.0143 (7) | 0.0185 (7) |
O1A | 0.0756 (9) | 0.0660 (9) | 0.0859 (11) | −0.0168 (7) | 0.0370 (8) | −0.0069 (7) |
N3 | 0.0579 (9) | 0.0605 (10) | 0.0486 (9) | −0.0056 (7) | 0.0167 (7) | −0.0054 (7) |
C15 | 0.0921 (17) | 0.0924 (18) | 0.0793 (18) | 0.0216 (13) | 0.0503 (14) | 0.0053 (13) |
C14 | 0.0887 (16) | 0.0752 (15) | 0.0704 (15) | 0.0203 (13) | 0.0326 (12) | −0.0036 (11) |
C2 | 0.0564 (11) | 0.0580 (11) | 0.0587 (13) | 0.0015 (9) | 0.0244 (9) | −0.0021 (9) |
O2A | 0.0881 (11) | 0.0622 (10) | 0.1022 (14) | −0.0114 (8) | 0.0316 (10) | −0.0060 (8) |
C6 | 0.0734 (14) | 0.0752 (14) | 0.0568 (13) | 0.0012 (11) | 0.0255 (11) | 0.0095 (10) |
C11 | 0.0531 (10) | 0.0634 (11) | 0.0474 (10) | 0.0017 (8) | 0.0183 (8) | −0.0011 (8) |
F14 | 0.1472 (16) | 0.0877 (11) | 0.1173 (13) | 0.0434 (10) | 0.0665 (12) | 0.0034 (9) |
F24 | 0.0777 (11) | 0.162 (2) | 0.185 (2) | 0.0313 (12) | 0.0582 (12) | 0.0364 (16) |
C21 | 0.0563 (11) | 0.0649 (12) | 0.0624 (13) | −0.0136 (9) | 0.0187 (9) | 0.0031 (9) |
C12 | 0.0585 (11) | 0.0707 (13) | 0.0541 (12) | −0.0015 (9) | 0.0234 (9) | 0.0000 (9) |
C16 | 0.0751 (14) | 0.0802 (15) | 0.0675 (14) | 0.0080 (11) | 0.0398 (11) | 0.0079 (11) |
C22 | 0.0636 (13) | 0.0877 (17) | 0.0702 (16) | −0.0085 (12) | 0.0237 (12) | −0.0008 (12) |
C13 | 0.0814 (15) | 0.0664 (14) | 0.0654 (14) | 0.0034 (11) | 0.0263 (12) | 0.0054 (10) |
C26 | 0.0651 (13) | 0.0838 (16) | 0.0676 (15) | −0.0141 (11) | 0.0128 (11) | 0.0031 (12) |
C5 | 0.0717 (13) | 0.0864 (15) | 0.0456 (12) | −0.0044 (11) | 0.0176 (10) | −0.0026 (10) |
C4 | 0.0726 (14) | 0.0898 (17) | 0.0499 (13) | −0.0127 (12) | 0.0150 (10) | −0.0083 (11) |
C25 | 0.0593 (14) | 0.107 (2) | 0.087 (2) | −0.0087 (14) | 0.0090 (13) | 0.0186 (16) |
C23 | 0.0815 (18) | 0.106 (2) | 0.100 (2) | −0.0009 (15) | 0.0451 (16) | 0.0015 (17) |
C24 | 0.0600 (14) | 0.105 (2) | 0.120 (3) | 0.0056 (13) | 0.0396 (15) | 0.0253 (18) |
C5A | 0.112 (2) | 0.115 (3) | 0.084 (2) | −0.018 (2) | 0.0510 (18) | −0.0276 (17) |
S1—O1B | 1.4277 (16) | C11—C16 | 1.385 (3) |
S1—O1A | 1.4292 (16) | F24—C24 | 1.365 (3) |
S1—N1 | 1.6364 (17) | C21—C22 | 1.366 (4) |
S1—C11 | 1.760 (2) | C21—C26 | 1.395 (3) |
S2—O2A | 1.4264 (18) | C12—C13 | 1.383 (3) |
S2—O2B | 1.4296 (16) | C12—H12 | 0.95 (3) |
S2—N3 | 1.6300 (18) | C16—H16 | 0.91 (3) |
S2—C21 | 1.767 (2) | C22—C23 | 1.373 (4) |
N1—C2 | 1.452 (3) | C22—H22 | 0.89 (3) |
N1—C6 | 1.471 (3) | C13—H13 | 0.87 (3) |
N3—C2 | 1.474 (3) | C26—C25 | 1.386 (4) |
N3—C4 | 1.482 (3) | C26—H26 | 0.98 (3) |
C15—C14 | 1.358 (4) | C5—C5A | 1.312 (4) |
C15—C16 | 1.376 (4) | C5—C4 | 1.495 (3) |
C15—H15 | 1.00 (3) | C4—H4A | 0.98 (3) |
C14—F14 | 1.353 (3) | C4—H4B | 1.02 (3) |
C14—C13 | 1.372 (4) | C25—C24 | 1.360 (5) |
C2—H2A | 0.95 (2) | C25—H25 | 0.89 (3) |
C2—H2B | 0.95 (3) | C23—C24 | 1.369 (5) |
C6—C5 | 1.500 (3) | C23—H23 | 0.99 (4) |
C6—H6A | 1.03 (3) | C5A—H5A | 0.86 (4) |
C6—H6B | 0.92 (3) | C5A—H5B | 0.95 (3) |
C11—C12 | 1.383 (3) | ||
O1B—S1—O1A | 120.18 (10) | C22—C21—C26 | 121.3 (2) |
O1B—S1—N1 | 106.27 (9) | C22—C21—S2 | 119.56 (18) |
O1A—S1—N1 | 105.69 (9) | C26—C21—S2 | 119.1 (2) |
O1B—S1—C11 | 107.82 (10) | C13—C12—C11 | 119.2 (2) |
O1A—S1—C11 | 107.20 (10) | C13—C12—H12 | 119.3 (16) |
N1—S1—C11 | 109.38 (8) | C11—C12—H12 | 121.5 (16) |
O2A—S2—O2B | 119.85 (11) | C15—C16—C11 | 119.6 (2) |
O2A—S2—N3 | 107.29 (11) | C15—C16—H16 | 120.5 (17) |
O2B—S2—N3 | 105.99 (9) | C11—C16—H16 | 119.9 (17) |
O2A—S2—C21 | 109.16 (10) | C21—C22—C23 | 120.3 (3) |
O2B—S2—C21 | 106.82 (11) | C21—C22—H22 | 120.8 (17) |
N3—S2—C21 | 107.09 (9) | C23—C22—H22 | 118.9 (17) |
C2—N1—C6 | 113.48 (17) | C14—C13—C12 | 118.5 (2) |
C2—N1—S1 | 119.26 (14) | C14—C13—H13 | 118.1 (19) |
C6—N1—S1 | 119.07 (15) | C12—C13—H13 | 123.4 (19) |
C2—N3—C4 | 112.12 (18) | C25—C26—C21 | 118.4 (3) |
C2—N3—S2 | 115.92 (14) | C25—C26—H26 | 122.5 (17) |
C4—N3—S2 | 118.75 (14) | C21—C26—H26 | 119.1 (17) |
C14—C15—C16 | 118.7 (2) | C5A—C5—C4 | 123.1 (3) |
C14—C15—H15 | 118.7 (19) | C5A—C5—C6 | 122.5 (3) |
C16—C15—H15 | 122.6 (19) | C4—C5—C6 | 114.4 (2) |
F14—C14—C15 | 119.3 (2) | N3—C4—C5 | 107.86 (18) |
F14—C14—C13 | 117.5 (3) | N3—C4—H4A | 108.4 (17) |
C15—C14—C13 | 123.2 (2) | C5—C4—H4A | 109.1 (16) |
N1—C2—N3 | 110.22 (16) | N3—C4—H4B | 111.5 (16) |
N1—C2—H2A | 110.6 (13) | C5—C4—H4B | 111.1 (17) |
N3—C2—H2A | 109.4 (14) | H4A—C4—H4B | 109 (2) |
N1—C2—H2B | 106.9 (15) | C24—C25—C26 | 118.5 (3) |
N3—C2—H2B | 109.7 (15) | C24—C25—H25 | 119 (2) |
H2A—C2—H2B | 110 (2) | C26—C25—H25 | 122 (2) |
N1—C6—C5 | 111.67 (18) | C24—C23—C22 | 117.8 (3) |
N1—C6—H6A | 107.4 (15) | C24—C23—H23 | 119 (2) |
C5—C6—H6A | 107.2 (16) | C22—C23—H23 | 123 (2) |
N1—C6—H6B | 104.1 (16) | C25—C24—F24 | 119.0 (3) |
C5—C6—H6B | 112.0 (17) | C25—C24—C23 | 123.7 (3) |
H6A—C6—H6B | 114 (2) | F24—C24—C23 | 117.3 (4) |
C12—C11—C16 | 120.9 (2) | C5—C5A—H5A | 125 (2) |
C12—C11—S1 | 119.42 (15) | C5—C5A—H5B | 116.5 (19) |
C16—C11—S1 | 119.63 (18) | H5A—C5A—H5B | 118 (3) |
O1B—S1—N1—C2 | 33.61 (17) | N3—S2—C21—C22 | 100.78 (19) |
O1A—S1—N1—C2 | 162.35 (15) | O2A—S2—C21—C26 | 38.6 (2) |
C11—S1—N1—C2 | −82.54 (16) | O2B—S2—C21—C26 | 169.55 (17) |
O1B—S1—N1—C6 | −179.89 (15) | N3—S2—C21—C26 | −77.25 (19) |
O1A—S1—N1—C6 | −51.15 (17) | C16—C11—C12—C13 | −1.6 (3) |
C11—S1—N1—C6 | 63.96 (17) | S1—C11—C12—C13 | 178.80 (17) |
O2A—S2—N3—C2 | −175.59 (14) | C14—C15—C16—C11 | 0.4 (4) |
O2B—S2—N3—C2 | 55.26 (16) | C12—C11—C16—C15 | 1.2 (4) |
C21—S2—N3—C2 | −58.51 (16) | S1—C11—C16—C15 | −179.2 (2) |
O2A—S2—N3—C4 | −37.5 (2) | C26—C21—C22—C23 | −0.6 (4) |
O2B—S2—N3—C4 | −166.65 (18) | S2—C21—C22—C23 | −178.6 (2) |
C21—S2—N3—C4 | 79.59 (19) | F14—C14—C13—C12 | −178.6 (2) |
C16—C15—C14—F14 | 178.1 (2) | C15—C14—C13—C12 | 1.2 (4) |
C16—C15—C14—C13 | −1.6 (5) | C11—C12—C13—C14 | 0.5 (3) |
C6—N1—C2—N3 | −55.2 (2) | C22—C21—C26—C25 | 0.0 (4) |
S1—N1—C2—N3 | 93.03 (18) | S2—C21—C26—C25 | 178.0 (2) |
C4—N3—C2—N1 | 60.7 (2) | N1—C6—C5—C5A | 133.0 (3) |
S2—N3—C2—N1 | −158.48 (14) | N1—C6—C5—C4 | −48.4 (3) |
C2—N1—C6—C5 | 49.1 (3) | C2—N3—C4—C5 | −58.2 (3) |
S1—N1—C6—C5 | −99.2 (2) | S2—N3—C4—C5 | 162.25 (17) |
O1B—S1—C11—C12 | −37.86 (19) | C5A—C5—C4—N3 | −129.2 (3) |
O1A—S1—C11—C12 | −168.57 (16) | C6—C5—C4—N3 | 52.2 (3) |
N1—S1—C11—C12 | 77.29 (18) | C21—C26—C25—C24 | 0.7 (4) |
O1B—S1—C11—C16 | 142.56 (17) | C21—C22—C23—C24 | 0.4 (4) |
O1A—S1—C11—C16 | 11.9 (2) | C26—C25—C24—F24 | 179.5 (2) |
N1—S1—C11—C16 | −102.29 (18) | C26—C25—C24—C23 | −0.9 (5) |
O2A—S2—C21—C22 | −143.37 (19) | C22—C23—C24—C25 | 0.3 (5) |
O2B—S2—C21—C22 | −12.4 (2) | C22—C23—C24—F24 | 179.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1B | 0.95 (2) | 2.39 (2) | 2.852 (3) | 109 (2) |
C22—H22···O2B | 0.89 (3) | 2.51 (3) | 2.873 (3) | 105 (1) |
C16—H16···O1A | 0.91 (3) | 2.51 (3) | 2.884 (3) | 105 (2) |
C4—H4B···O2A | 1.02 (3) | 2.49 (3) | 2.897 (3) | 103 (2) |
C2—H2A···O2B | 0.95 (2) | 2.52 (2) | 2.947 (3) | 108 (2) |
C13—H13···O2Bi | 0.87 (3) | 2.54 (3) | 3.386 (3) | 163 (2) |
C2—H2B···O2Aii | 0.95 (3) | 2.53 (3) | 3.476 (3) | 173 (2) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H16F2N2O4S2 |
Mr | 414.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 13.8591 (2), 10.8218 (1), 13.8946 (2) |
β (°) | 114.751 (1) |
V (Å3) | 1892.48 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.97 |
Crystal size (mm) | 0.18 × 0.16 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.686, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9044, 3177, 2783 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.124, 1.07 |
No. of reflections | 3177 |
No. of parameters | 309 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.35 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1990), SHELXTL (Sheldrick, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1B | 0.95 (2) | 2.39 (2) | 2.852 (3) | 109 (2) |
C22—H22···O2B | 0.89 (3) | 2.51 (3) | 2.873 (3) | 105 (1) |
C16—H16···O1A | 0.91 (3) | 2.51 (3) | 2.884 (3) | 105 (2) |
C4—H4B···O2A | 1.02 (3) | 2.49 (3) | 2.897 (3) | 103 (2) |
C2—H2A···O2B | 0.95 (2) | 2.52 (2) | 2.947 (3) | 108 (2) |
C13—H13···O2Bi | 0.87 (3) | 2.54 (3) | 3.386 (3) | 163 (2) |
C2—H2B···O2Aii | 0.95 (3) | 2.53 (3) | 3.476 (3) | 173 (2) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y−1/2, −z+1/2. |
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Polyamine rings, or ring systems, are necessary precursors for several of the most potent energetic materials known, such as RDX, HMX, and CL20. The C—N bonds holding these molecules together are weaker than C—C bonds, and thus release more energy when they are dissociated and recombined to form gaseous products, such as N2 and CO2. The backbone rings in these molecules are first synthesized with no energetic substituents, often through fairly simple condensation reactions between amines and a reactive carbonyl compound (e.g. glyoxal or formaldehyde). However, (I) results from a more complex condensation wherein the two N atoms seen in the central ring of the product (I) are already linked together in reactant (a). This reaction produces a diazacyclohexane ring with the amino N atoms already protected or stabilized by fluorobenzenesulfonamide groups, and an exocyclic double bond. This particular `designed' product, (I), was targeted as a precursor for further synthetic addition of energetic groups to produce novel analogs of 1,3,5-trinitrotriazacyclohexane (RDX).
The structure of the molecule of (I) and its packing are not unusual in any way (Figs. 1 and 2). There are five short intramolecular C—H···O contacts (Table 1) but they are not very short and are quite bent, so they may not be even weak `hydrogen bonds' but just unavoidable contacts caused by substitution of two bulky groups on each sulfonyl group. The remaining two C—H···O intermolecular bonds shown in Table 1 are close to linear [C—H···O angles of 163 (2) and 173 (2)°], and so appear to be hydrogen bonds, but weak ones, since their H···O contact distances [2.53 (3) and 2.54 (3) Å] are very slightly less than the expected van der Waals H···O contact of 2.62 Å (Rowland & Taylor, 1996).