Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020347/bt6090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020347/bt6090Isup2.hkl |
CCDC reference: 180525
The title compound was synthesized by the reaction of p-acetanilide benzoylmethyl sulfone with 4-nitrophenyldiazonium chloride. The reactions was carried out in alkaline ethyl alcohol solution (Zakrzewski, 1996). The crystal used for data collection was obtained by vapour diffusion; the sample was dissolved in a 2:1 mixture of chloroform and isopropyl alcohol and equilibrated at room temperature against pure isopropyl alcohol for 15 d.
All H atoms were placed in calculated positions and were treated as riding on the adjacent N or C atom. They were refined with individual isotropic displacement parameters equal 1.2 times the value of the equivalent displacement parameters of the parent N or C atom.
Data collection: KM-4 User's Guide (Kuma, 1991); cell refinement: KM-4 User's Guide); data reduction: DATAPROC (Gałdecki et al., 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SYBYL (Tripos, 1996) and XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.
C22H18N4O6S | Z = 4 |
Mr = 466.46 | F(000) = 968 |
Triclinic, P1 | Dx = 1.454 Mg m−3 |
a = 7.461 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 11.663 (2) Å | Cell parameters from 50 reflections |
c = 24.621 (5) Å | θ = 5–25° |
α = 94.31 (3)° | µ = 1.78 mm−1 |
β = 90.88 (3)° | T = 293 K |
γ = 94.01 (3)° | Ellipsoid, yellow |
V = 2130.7 (6) Å3 | 0.45 × 0.35 × 0.35 mm |
Kuma KM-4 diffractometer | 2363 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 50.1°, θmin = 3.6° |
ω–2θ scans | h = −7→7 |
Absorption correction: ψ scan (XEMP; Siemens, 1989) | k = −11→11 |
Tmin = 0.463, Tmax = 0.537 | l = 0→24 |
4490 measured reflections | 3 standard reflections every 100 reflections |
4354 independent reflections | intensity decay: 46% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Geom |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.104P)2 + 0.8456P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4354 reflections | Δρmax = 0.46 e Å−3 |
596 parameters | Δρmin = −0.25 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: 0.0027 (4) |
C22H18N4O6S | γ = 94.01 (3)° |
Mr = 466.46 | V = 2130.7 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.461 (1) Å | Cu Kα radiation |
b = 11.663 (2) Å | µ = 1.78 mm−1 |
c = 24.621 (5) Å | T = 293 K |
α = 94.31 (3)° | 0.45 × 0.35 × 0.35 mm |
β = 90.88 (3)° |
Kuma KM-4 diffractometer | 2363 reflections with I > 2σ(I) |
Absorption correction: ψ scan (XEMP; Siemens, 1989) | Rint = 0.052 |
Tmin = 0.463, Tmax = 0.537 | θmax = 50.1° |
4490 measured reflections | 3 standard reflections every 100 reflections |
4354 independent reflections | intensity decay: 46% |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.180 | Geom |
S = 1.07 | Δρmax = 0.46 e Å−3 |
4354 reflections | Δρmin = −0.25 e Å−3 |
596 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 | −0.0944 (3) | 0.60069 (14) | 0.68116 (6) | 0.0575 (6) | |
O1 | −0.2827 (6) | 0.5861 (4) | 0.66654 (17) | 0.0666 (13) | |
O2 | −0.0384 (7) | 0.6916 (3) | 0.72228 (16) | 0.0742 (14) | |
O3 | −0.0914 (6) | 0.3731 (4) | 0.62354 (16) | 0.0643 (13) | |
O4 | 0.6041 (7) | 0.6300 (4) | 0.5047 (2) | 0.0820 (15) | |
O5 | 0.2459 (10) | 0.5814 (6) | 1.0414 (2) | 0.119 (2) | |
O6 | 0.3280 (9) | 0.4135 (6) | 1.0206 (2) | 0.109 (2) | |
N1 | 0.0356 (6) | 0.4633 (4) | 0.75725 (19) | 0.0456 (13) | |
N2 | 0.0577 (7) | 0.5511 (4) | 0.79382 (19) | 0.0530 (14) | |
H2 | 0.0377 | 0.6192 | 0.7852 | 0.064* | |
N3 | 0.3134 (8) | 0.6430 (4) | 0.4794 (2) | 0.0558 (15) | |
H3 | 0.2462 | 0.6503 | 0.4514 | 0.067* | |
N4 | 0.2675 (9) | 0.5019 (7) | 1.0084 (3) | 0.0795 (19) | |
C1 | −0.0260 (8) | 0.4709 (5) | 0.7074 (2) | 0.0459 (16) | |
C2 | −0.0470 (8) | 0.3650 (5) | 0.6715 (2) | 0.0486 (16) | |
C3 | −0.0097 (8) | 0.2498 (5) | 0.6899 (2) | 0.0434 (16) | |
C4 | −0.0593 (8) | 0.2134 (6) | 0.7407 (2) | 0.0508 (17) | |
H4 | −0.1106 | 0.2632 | 0.7663 | 0.061* | |
C5 | −0.0307 (9) | 0.1020 (6) | 0.7522 (3) | 0.0593 (19) | |
H5 | −0.0623 | 0.0772 | 0.7860 | 0.071* | |
C6 | 0.0425 (9) | 0.0280 (6) | 0.7152 (3) | 0.0630 (19) | |
H6 | 0.0594 | −0.0469 | 0.7237 | 0.076* | |
C7 | 0.0918 (9) | 0.0627 (6) | 0.6651 (3) | 0.0615 (19) | |
H7 | 0.1450 | 0.0124 | 0.6402 | 0.074* | |
C8 | 0.0622 (8) | 0.1717 (6) | 0.6523 (2) | 0.0507 (17) | |
H8 | 0.0905 | 0.1942 | 0.6178 | 0.061* | |
C9 | 0.0302 (9) | 0.6180 (5) | 0.6232 (2) | 0.0499 (17) | |
C10 | 0.2159 (10) | 0.6329 (6) | 0.6258 (3) | 0.068 (2) | |
H10 | 0.2750 | 0.6373 | 0.6595 | 0.082* | |
C11 | 0.3144 (10) | 0.6412 (6) | 0.5792 (3) | 0.070 (2) | |
H11 | 0.4392 | 0.6486 | 0.5813 | 0.084* | |
C12 | 0.2250 (9) | 0.6385 (5) | 0.5288 (2) | 0.0472 (16) | |
C13 | 0.0403 (9) | 0.6305 (5) | 0.5270 (2) | 0.0498 (17) | |
H13 | −0.0194 | 0.6334 | 0.4937 | 0.060* | |
C14 | −0.0581 (9) | 0.6182 (5) | 0.5731 (2) | 0.0521 (17) | |
H14 | −0.1830 | 0.6101 | 0.5708 | 0.063* | |
C15 | 0.4910 (11) | 0.6373 (6) | 0.4697 (3) | 0.0595 (19) | |
C16 | 0.5390 (10) | 0.6396 (7) | 0.4099 (3) | 0.078 (2) | |
H161 | 0.4318 | 0.6443 | 0.3884 | 0.094* | |
H162 | 0.5952 | 0.5705 | 0.3984 | 0.094* | |
H163 | 0.6203 | 0.7054 | 0.4052 | 0.094* | |
C17 | 0.1141 (8) | 0.5338 (5) | 0.8469 (2) | 0.0438 (16) | |
C18 | 0.1098 (10) | 0.6252 (6) | 0.8848 (3) | 0.069 (2) | |
H18 | 0.0714 | 0.6947 | 0.8745 | 0.083* | |
C19 | 0.1612 (10) | 0.6158 (6) | 0.9374 (3) | 0.069 (2) | |
H19 | 0.1595 | 0.6786 | 0.9630 | 0.083* | |
C20 | 0.2148 (9) | 0.5137 (6) | 0.9520 (2) | 0.0553 (18) | |
C21 | 0.2229 (9) | 0.4203 (6) | 0.9148 (3) | 0.0586 (18) | |
H21 | 0.2640 | 0.3516 | 0.9253 | 0.070* | |
C22 | 0.1685 (9) | 0.4305 (5) | 0.8612 (2) | 0.0543 (18) | |
H22 | 0.1691 | 0.3680 | 0.8355 | 0.065* | |
S2 | 0.3812 (3) | −0.12009 (15) | 0.81709 (6) | 0.0611 (6) | |
O7 | 0.1943 (6) | −0.1145 (4) | 0.82986 (17) | 0.0755 (15) | |
O8 | 0.4308 (8) | −0.2097 (4) | 0.77737 (18) | 0.0832 (16) | |
O9 | 0.4085 (6) | 0.1102 (4) | 0.87387 (17) | 0.0671 (13) | |
O10 | 1.0833 (7) | −0.1345 (4) | 0.9978 (2) | 0.0764 (14) | |
O11 | 0.8034 (11) | −0.0880 (6) | 0.4673 (2) | 0.135 (3) | |
O12 | 0.7688 (11) | 0.0883 (6) | 0.4766 (2) | 0.134 (3) | |
N5 | 0.5207 (7) | 0.0236 (4) | 0.7420 (2) | 0.0518 (14) | |
N6 | 0.5450 (7) | −0.0623 (5) | 0.7064 (2) | 0.0608 (15) | |
H61 | 0.5225 | −0.1319 | 0.7150 | 0.073* | |
N7 | 0.7917 (8) | −0.1397 (4) | 1.02280 (19) | 0.0546 (14) | |
H71 | 0.7247 | −0.1418 | 1.0509 | 0.066* | |
N8 | 0.7684 (9) | −0.0056 (7) | 0.4943 (2) | 0.0769 (19) | |
C23 | 0.4591 (8) | 0.0122 (5) | 0.7907 (2) | 0.0468 (16) | |
C24 | 0.4494 (8) | 0.1188 (6) | 0.8262 (3) | 0.0502 (17) | |
C25 | 0.4944 (8) | 0.2356 (5) | 0.8072 (2) | 0.0473 (16) | |
C26 | 0.4390 (8) | 0.2672 (6) | 0.7565 (2) | 0.0522 (17) | |
H26 | 0.3802 | 0.2134 | 0.7313 | 0.063* | |
C27 | 0.4731 (10) | 0.3798 (6) | 0.7446 (3) | 0.064 (2) | |
H27 | 0.4335 | 0.4019 | 0.7112 | 0.077* | |
C28 | 0.5634 (10) | 0.4606 (6) | 0.7802 (3) | 0.0646 (19) | |
H28 | 0.5856 | 0.5361 | 0.7710 | 0.077* | |
C29 | 0.6208 (9) | 0.4278 (6) | 0.8300 (3) | 0.0638 (19) | |
H29 | 0.6836 | 0.4812 | 0.8545 | 0.077* | |
C30 | 0.5854 (8) | 0.3171 (6) | 0.8431 (3) | 0.0545 (18) | |
H30 | 0.6230 | 0.2960 | 0.8769 | 0.065* | |
C31 | 0.5068 (10) | −0.1310 (5) | 0.8768 (2) | 0.0505 (17) | |
C32 | 0.6882 (10) | −0.1437 (6) | 0.8750 (3) | 0.066 (2) | |
H32 | 0.7447 | −0.1499 | 0.8416 | 0.079* | |
C33 | 0.7864 (9) | −0.1472 (6) | 0.9224 (3) | 0.0641 (19) | |
H33 | 0.9097 | −0.1542 | 0.9212 | 0.077* | |
C34 | 0.7019 (9) | −0.1404 (5) | 0.9721 (2) | 0.0485 (16) | |
C35 | 0.5179 (9) | −0.1324 (5) | 0.9734 (2) | 0.0503 (17) | |
H35 | 0.4598 | −0.1316 | 1.0066 | 0.060* | |
C36 | 0.4204 (9) | −0.1255 (5) | 0.9263 (2) | 0.0543 (17) | |
H36 | 0.2974 | −0.1173 | 0.9275 | 0.065* | |
C37 | 0.9733 (11) | −0.1362 (6) | 1.0328 (3) | 0.0608 (18) | |
C38 | 1.0242 (10) | −0.1338 (7) | 1.0928 (3) | 0.079 (2) | |
H381 | 0.9173 | −0.1360 | 1.1140 | 0.094* | |
H382 | 1.0974 | −0.0645 | 1.1033 | 0.094* | |
H383 | 1.0902 | −0.1995 | 1.0991 | 0.094* | |
C39 | 0.6077 (8) | −0.0420 (6) | 0.6540 (2) | 0.0509 (17) | |
C40 | 0.6573 (11) | −0.1351 (6) | 0.6228 (3) | 0.073 (2) | |
H40 | 0.6544 | −0.2069 | 0.6371 | 0.087* | |
C41 | 0.7114 (11) | −0.1235 (7) | 0.5706 (3) | 0.076 (2) | |
H41 | 0.7464 | −0.1869 | 0.5491 | 0.091* | |
C42 | 0.7132 (9) | −0.0178 (6) | 0.5504 (2) | 0.0550 (17) | |
C43 | 0.6705 (9) | 0.0763 (6) | 0.5816 (3) | 0.0638 (19) | |
H43 | 0.6789 | 0.1484 | 0.5677 | 0.077* | |
C44 | 0.6137 (9) | 0.0648 (6) | 0.6349 (3) | 0.0622 (19) | |
H44 | 0.5810 | 0.1283 | 0.6568 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0791 (14) | 0.0563 (12) | 0.0398 (10) | 0.0141 (9) | −0.0028 (9) | 0.0148 (8) |
O1 | 0.062 (3) | 0.081 (3) | 0.062 (3) | 0.018 (3) | 0.004 (2) | 0.028 (2) |
O2 | 0.136 (4) | 0.046 (3) | 0.041 (3) | 0.019 (3) | −0.012 (3) | 0.000 (2) |
O3 | 0.097 (4) | 0.063 (3) | 0.034 (3) | 0.004 (3) | −0.016 (2) | 0.009 (2) |
O4 | 0.064 (3) | 0.111 (4) | 0.072 (3) | 0.005 (3) | −0.019 (3) | 0.017 (3) |
O5 | 0.190 (7) | 0.116 (5) | 0.045 (3) | −0.003 (5) | −0.030 (4) | −0.008 (4) |
O6 | 0.164 (6) | 0.100 (5) | 0.064 (4) | −0.001 (4) | −0.043 (4) | 0.028 (3) |
N1 | 0.050 (3) | 0.049 (3) | 0.038 (3) | 0.004 (3) | 0.000 (2) | 0.004 (3) |
N2 | 0.080 (4) | 0.045 (3) | 0.035 (3) | 0.007 (3) | −0.007 (3) | 0.005 (3) |
N3 | 0.056 (4) | 0.072 (4) | 0.043 (4) | 0.001 (3) | −0.011 (3) | 0.025 (3) |
N4 | 0.108 (6) | 0.085 (5) | 0.043 (4) | −0.016 (4) | −0.017 (4) | 0.010 (4) |
C1 | 0.054 (4) | 0.054 (4) | 0.032 (4) | 0.005 (3) | 0.000 (3) | 0.015 (3) |
C2 | 0.058 (4) | 0.056 (4) | 0.032 (4) | 0.003 (3) | 0.000 (3) | 0.007 (3) |
C3 | 0.048 (4) | 0.047 (4) | 0.035 (4) | −0.002 (3) | −0.012 (3) | 0.007 (3) |
C4 | 0.068 (5) | 0.055 (5) | 0.029 (4) | −0.002 (3) | −0.002 (3) | 0.006 (3) |
C5 | 0.075 (5) | 0.062 (5) | 0.040 (4) | −0.007 (4) | −0.014 (3) | 0.014 (4) |
C6 | 0.076 (5) | 0.048 (4) | 0.065 (5) | 0.004 (4) | −0.018 (4) | 0.009 (4) |
C7 | 0.076 (5) | 0.054 (5) | 0.054 (5) | 0.009 (4) | −0.009 (4) | −0.003 (4) |
C8 | 0.058 (4) | 0.061 (5) | 0.032 (4) | 0.001 (4) | −0.003 (3) | 0.004 (3) |
C9 | 0.060 (5) | 0.055 (4) | 0.036 (4) | 0.002 (3) | −0.006 (3) | 0.013 (3) |
C10 | 0.073 (6) | 0.087 (5) | 0.042 (5) | −0.012 (4) | −0.020 (4) | 0.013 (4) |
C11 | 0.060 (5) | 0.107 (6) | 0.043 (5) | −0.010 (4) | −0.015 (4) | 0.022 (4) |
C12 | 0.056 (5) | 0.047 (4) | 0.040 (4) | 0.000 (3) | −0.010 (3) | 0.015 (3) |
C13 | 0.063 (5) | 0.052 (4) | 0.036 (4) | 0.006 (3) | −0.011 (3) | 0.013 (3) |
C14 | 0.058 (4) | 0.057 (4) | 0.043 (4) | 0.009 (3) | −0.012 (4) | 0.011 (3) |
C15 | 0.062 (6) | 0.055 (5) | 0.062 (5) | −0.002 (4) | −0.009 (4) | 0.015 (3) |
C16 | 0.069 (5) | 0.098 (6) | 0.069 (5) | 0.007 (4) | 0.000 (4) | 0.022 (4) |
C17 | 0.059 (4) | 0.045 (4) | 0.027 (4) | −0.003 (3) | 0.000 (3) | 0.007 (3) |
C18 | 0.114 (6) | 0.046 (4) | 0.047 (4) | 0.009 (4) | −0.014 (4) | 0.004 (4) |
C19 | 0.113 (6) | 0.058 (5) | 0.036 (4) | 0.000 (4) | −0.005 (4) | 0.000 (4) |
C20 | 0.068 (5) | 0.065 (5) | 0.031 (4) | −0.009 (4) | −0.008 (3) | 0.005 (4) |
C21 | 0.076 (5) | 0.052 (4) | 0.049 (4) | 0.008 (4) | −0.005 (3) | 0.014 (4) |
C22 | 0.084 (5) | 0.044 (4) | 0.035 (4) | 0.005 (4) | −0.002 (3) | 0.005 (3) |
S2 | 0.0821 (15) | 0.0628 (12) | 0.0382 (10) | −0.0079 (10) | −0.0039 (9) | 0.0164 (9) |
O7 | 0.066 (4) | 0.102 (4) | 0.058 (3) | −0.018 (3) | −0.005 (2) | 0.035 (3) |
O8 | 0.148 (5) | 0.055 (3) | 0.044 (3) | −0.010 (3) | −0.007 (3) | 0.008 (2) |
O9 | 0.096 (4) | 0.076 (3) | 0.031 (3) | 0.012 (3) | 0.013 (2) | 0.011 (2) |
O10 | 0.061 (3) | 0.101 (4) | 0.069 (3) | 0.013 (3) | 0.014 (3) | 0.010 (3) |
O11 | 0.239 (9) | 0.117 (5) | 0.052 (4) | 0.044 (5) | 0.047 (4) | −0.006 (4) |
O12 | 0.231 (8) | 0.105 (5) | 0.073 (4) | 0.015 (5) | 0.047 (4) | 0.034 (4) |
N5 | 0.057 (3) | 0.054 (4) | 0.044 (4) | 0.008 (3) | −0.011 (3) | 0.001 (3) |
N6 | 0.084 (4) | 0.044 (3) | 0.053 (4) | 0.001 (3) | −0.001 (3) | 0.006 (3) |
N7 | 0.056 (4) | 0.072 (4) | 0.039 (3) | 0.008 (3) | 0.005 (3) | 0.017 (3) |
N8 | 0.094 (5) | 0.093 (6) | 0.045 (4) | 0.012 (4) | 0.013 (3) | 0.004 (4) |
C23 | 0.058 (4) | 0.055 (4) | 0.029 (4) | 0.004 (3) | 0.001 (3) | 0.018 (3) |
C24 | 0.047 (4) | 0.065 (5) | 0.040 (4) | 0.005 (3) | 0.000 (3) | 0.005 (4) |
C25 | 0.053 (4) | 0.058 (4) | 0.033 (4) | 0.010 (3) | 0.006 (3) | 0.006 (3) |
C26 | 0.062 (4) | 0.061 (5) | 0.035 (4) | 0.008 (3) | −0.001 (3) | 0.007 (3) |
C27 | 0.089 (6) | 0.066 (5) | 0.040 (4) | 0.016 (4) | 0.005 (4) | 0.012 (4) |
C28 | 0.082 (5) | 0.057 (5) | 0.057 (5) | 0.002 (4) | 0.018 (4) | 0.017 (4) |
C29 | 0.061 (5) | 0.063 (5) | 0.064 (5) | −0.014 (4) | 0.007 (4) | −0.003 (4) |
C30 | 0.053 (4) | 0.071 (5) | 0.041 (4) | 0.006 (4) | −0.003 (3) | 0.007 (4) |
C31 | 0.064 (5) | 0.053 (4) | 0.037 (4) | 0.005 (3) | 0.001 (3) | 0.019 (3) |
C32 | 0.075 (6) | 0.093 (6) | 0.034 (4) | 0.020 (4) | 0.011 (4) | 0.017 (4) |
C33 | 0.064 (5) | 0.090 (5) | 0.042 (4) | 0.024 (4) | 0.011 (4) | 0.010 (4) |
C34 | 0.061 (5) | 0.051 (4) | 0.035 (4) | 0.007 (3) | 0.003 (3) | 0.011 (3) |
C35 | 0.064 (5) | 0.053 (4) | 0.036 (4) | 0.000 (3) | 0.009 (3) | 0.016 (3) |
C36 | 0.061 (5) | 0.065 (5) | 0.039 (4) | −0.001 (3) | 0.001 (4) | 0.020 (3) |
C37 | 0.067 (6) | 0.061 (5) | 0.057 (5) | 0.006 (4) | 0.008 (4) | 0.018 (3) |
C38 | 0.066 (5) | 0.103 (6) | 0.069 (5) | 0.003 (4) | −0.010 (4) | 0.028 (4) |
C39 | 0.064 (5) | 0.058 (5) | 0.031 (4) | −0.001 (4) | −0.005 (3) | 0.005 (4) |
C40 | 0.114 (6) | 0.051 (5) | 0.054 (5) | 0.015 (4) | 0.008 (4) | 0.001 (4) |
C41 | 0.118 (7) | 0.066 (6) | 0.046 (5) | 0.029 (5) | 0.008 (4) | −0.001 (4) |
C42 | 0.069 (5) | 0.058 (5) | 0.037 (4) | 0.010 (4) | 0.002 (3) | −0.005 (4) |
C43 | 0.089 (6) | 0.053 (5) | 0.050 (5) | 0.001 (4) | 0.014 (4) | 0.014 (4) |
C44 | 0.083 (5) | 0.050 (5) | 0.053 (5) | 0.008 (4) | 0.012 (4) | −0.003 (4) |
S1—O1 | 1.440 (5) | S2—O7 | 1.439 (5) |
S1—O2 | 1.445 (4) | S2—O8 | 1.448 (5) |
S1—C1 | 1.793 (6) | S2—C23 | 1.783 (6) |
S1—C9 | 1.732 (6) | S2—C31 | 1.749 (6) |
O3—C2 | 1.234 (6) | O9—C24 | 1.228 (7) |
N1—N2 | 1.311 (6) | N5—N6 | 1.305 (7) |
N1—C1 | 1.316 (7) | N5—C23 | 1.302 (7) |
N2—C17 | 1.400 (7) | N6—C39 | 1.411 (8) |
C1—C2 | 1.461 (8) | C23—C24 | 1.472 (8) |
C2—C3 | 1.493 (8) | C24—C25 | 1.491 (8) |
O5—N4 | 1.207 (8) | O11—N8 | 1.174 (7) |
O6—N4 | 1.211 (8) | O12—N8 | 1.208 (8) |
N4—C20 | 1.457 (8) | N8—C42 | 1.462 (8) |
N3—C12 | 1.396 (8) | N7—C34 | 1.407 (8) |
N3—C15 | 1.355 (8) | N7—C37 | 1.371 (8) |
O4—C15 | 1.209 (8) | O10—C37 | 1.200 (8) |
C15—C16 | 1.521 (9) | C37—C38 | 1.518 (9) |
C3—C8 | 1.390 (8) | C25—C30 | 1.384 (8) |
C3—C4 | 1.397 (8) | C25—C26 | 1.392 (8) |
C4—C5 | 1.381 (8) | C26—C27 | 1.374 (8) |
C5—C6 | 1.356 (9) | C27—C28 | 1.371 (9) |
C6—C7 | 1.373 (9) | C28—C29 | 1.384 (9) |
C7—C8 | 1.365 (8) | C29—C30 | 1.363 (8) |
C9—C10 | 1.384 (9) | C31—C32 | 1.373 (9) |
C9—C14 | 1.390 (8) | C31—C36 | 1.387 (8) |
C10—C11 | 1.378 (9) | C32—C33 | 1.375 (9) |
C11—C12 | 1.397 (8) | C33—C34 | 1.384 (9) |
C12—C13 | 1.374 (8) | C34—C35 | 1.383 (8) |
C13—C14 | 1.373 (8) | C35—C36 | 1.369 (8) |
C17—C18 | 1.365 (8) | C39—C40 | 1.358 (9) |
C17—C22 | 1.366 (8) | C39—C44 | 1.362 (8) |
C18—C19 | 1.361 (9) | C40—C41 | 1.368 (9) |
C19—C20 | 1.354 (9) | C41—C42 | 1.363 (9) |
C20—C21 | 1.375 (9) | C42—C43 | 1.351 (9) |
C21—C22 | 1.390 (8) | C43—C44 | 1.399 (9) |
N2—H2 | 0.86 | N6—H61 | 0.86 |
N3—H3 | 0.86 | N7—H71 | 0.86 |
C4—H4 | 0.93 | C26—H26 | 0.93 |
C5—H5 | 0.93 | C27—H27 | 0.93 |
C6—H6 | 0.93 | C28—H28 | 0.93 |
C7—H7 | 0.93 | C29—H29 | 0.93 |
C8—H8 | 0.93 | C30—H30 | 0.93 |
C10—H10 | 0.93 | C32—H32 | 0.93 |
C11—H11 | 0.93 | C33—H33 | 0.93 |
C13—H13 | 0.93 | C35—H35 | 0.93 |
C14—H14 | 0.93 | C36—H36 | 0.93 |
C16—H161 | 0.96 | C38—H381 | 0.96 |
C16—H162 | 0.96 | C38—H382 | 0.96 |
C16—H163 | 0.96 | C38—H383 | 0.96 |
C18—H18 | 0.93 | C40—H40 | 0.93 |
C19—H19 | 0.93 | C41—H41 | 0.93 |
C21—H21 | 0.93 | C43—H43 | 0.93 |
C22—H22 | 0.93 | C44—H44 | 0.93 |
S1···O3 | 2.916 (4) | S2···O9 | 2.926 (5) |
S1···N2 | 3.091 (5) | S2···N6 | 3.104 (6) |
O1···C2 | 3.230 (7) | O7···C24 | 3.218 (8) |
O2···C2 | 3.915 (7) | O8···C24 | 3.920 (8) |
O1···N2 | 4.066 (7) | O7···N6 | 4.094 (7) |
O2···N2 | 2.620 (6) | O8···N6 | 2.651 (7) |
N2···C2 | 3.619 (8) | N6···C24 | 3.606 (9) |
O1—S1—O2 | 117.4 (3) | O7—S2—O8 | 118.3 (3) |
O1—S1—C1 | 109.3 (3) | O7—S2—C23 | 108.6 (3) |
O1—S1—C9 | 109.2 (3) | O7—S2—C31 | 109.7 (3) |
O2—S1—C1 | 105.2 (3) | O8—S2—C23 | 105.3 (3) |
O2—S1—C9 | 109.2 (3) | O8—S2—C31 | 107.8 (3) |
C1—S1—C9 | 105.5 (3) | C23—S2—C31 | 106.5 (3) |
N2—N1—C1 | 123.8 (5) | N6—N5—C23 | 124.4 (5) |
N1—N2—C17 | 119.9 (5) | N5—N6—C39 | 120.7 (6) |
N1—C1—C2 | 117.6 (5) | S2—C23—N5 | 125.8 (5) |
S1—C1—N1 | 124.7 (5) | S2—C23—C24 | 117.6 (5) |
S1—C1—C2 | 117.6 (4) | N5—C23—C24 | 116.6 (5) |
O3—C2—C1 | 117.8 (5) | O9—C24—C23 | 118.1 (6) |
O3—C2—C3 | 119.4 (5) | O9—C24—C25 | 119.1 (6) |
C1—C2—C3 | 122.8 (5) | C23—C24—C25 | 122.8 (5) |
O5—N4—O6 | 122.6 (7) | O11—N8—O12 | 122.2 (7) |
O5—N4—C20 | 117.8 (8) | O11—N8—C42 | 119.0 (7) |
O6—N4—C20 | 119.5 (7) | O12—N8—C42 | 118.7 (7) |
C12—N3—C15 | 128.7 (6) | C34—N7—C37 | 127.8 (6) |
O4—C15—N3 | 124.0 (7) | O10—C37—N7 | 123.7 (7) |
O4—C15—C16 | 121.7 (7) | O10—C37—C38 | 122.5 (7) |
N3—C15—C16 | 114.3 (6) | N7—C37—C38 | 113.8 (6) |
C8—C3—C4 | 118.9 (6) | C30—C25—C26 | 119.3 (6) |
C8—C3—C2 | 117.5 (5) | C30—C25—C24 | 117.9 (6) |
C4—C3—C2 | 123.3 (6) | C26—C25—C24 | 122.7 (6) |
C5—C4—C3 | 118.8 (6) | C27—C26—C25 | 118.4 (6) |
C6—C5—C4 | 121.3 (6) | C28—C27—C26 | 122.3 (6) |
C5—C6—C7 | 120.5 (6) | C27—C28—C29 | 118.8 (6) |
C8—C7—C6 | 119.5 (6) | C30—C29—C28 | 119.9 (6) |
C7—C8—C3 | 121.0 (6) | C29—C30—C25 | 121.3 (6) |
C10—C9—C14 | 119.3 (6) | C32—C31—C36 | 120.4 (6) |
C10—C9—S1 | 121.4 (5) | C32—C31—S2 | 120.8 (5) |
C14—C9—S1 | 119.4 (5) | C36—C31—S2 | 118.9 (5) |
C11—C10—C9 | 121.0 (6) | C31—C32—C33 | 120.0 (6) |
C10—C11—C12 | 119.4 (7) | C32—C33—C34 | 120.0 (6) |
C13—C12—C11 | 119.2 (6) | C33—C34—C35 | 119.5 (6) |
C13—C12—N3 | 117.4 (5) | C33—C34—N7 | 124.1 (6) |
C11—C12—N3 | 123.4 (6) | C35—C34—N7 | 116.4 (5) |
C14—C13—C12 | 121.5 (5) | C36—C35—C34 | 120.6 (6) |
C13—C14—C9 | 119.5 (6) | C35—C36—C31 | 119.4 (6) |
C18—C17—C22 | 120.6 (6) | C40—C39—C44 | 121.6 (6) |
C18—C17—N2 | 116.8 (6) | C40—C39—N6 | 116.6 (6) |
C22—C17—N2 | 122.5 (5) | C44—C39—N6 | 121.8 (6) |
C19—C18—C17 | 120.8 (7) | C39—C40—C41 | 120.1 (7) |
C20—C19—C18 | 119.0 (6) | C42—C41—C40 | 119.0 (7) |
C19—C20—C21 | 121.8 (6) | C43—C42—C41 | 121.5 (6) |
C19—C20—N4 | 119.5 (7) | C43—C42—N8 | 119.4 (7) |
C21—C20—N4 | 118.6 (7) | C41—C42—N8 | 119.1 (6) |
C20—C21—C22 | 118.7 (6) | C42—C43—C44 | 119.7 (6) |
C17—C22—C21 | 119.1 (6) | C39—C44—C43 | 118.0 (6) |
N1—N2—H2 | 120.0 | N5—N6—H61 | 119.7 |
C17—N2—H2 | 120.0 | C39—N6—H61 | 119.7 |
C15—N3—H3 | 115.6 | C37—N7—H71 | 116.1 |
C12—N3—H3 | 115.6 | C34—N7—H71 | 116.1 |
C5—C4—H4 | 120.6 | C27—C26—H26 | 120.8 |
C3—C4—H4 | 120.6 | C25—C26—H26 | 120.8 |
C6—C5—H5 | 119.4 | C28—C27—H27 | 118.8 |
C4—C5—H5 | 119.4 | C26—C27—H27 | 118.8 |
C5—C6—H6 | 119.7 | C27—C28—H28 | 120.6 |
C7—C6—H6 | 119.7 | C29—C28—H28 | 120.6 |
C8—C7—H7 | 120.3 | C30—C29—H29 | 120.1 |
C6—C7—H7 | 120.3 | C28—C29—H29 | 120.1 |
C7—C8—H8 | 119.5 | C29—C30—H30 | 119.4 |
C3—C8—H8 | 119.5 | C25—C30—H30 | 119.4 |
C11—C10—H10 | 119.5 | C31—C32—H32 | 120.0 |
C9—C10—H10 | 119.5 | C33—C32—H32 | 120.0 |
C10—C11—H11 | 120.3 | C32—C33—H33 | 120.0 |
C12—C11—H11 | 120.3 | C34—C33—H33 | 120.0 |
C14—C13—H13 | 119.3 | C36—C35—H35 | 119.7 |
C12—C13—H13 | 119.3 | C34—C35—H35 | 119.7 |
C13—C14—H14 | 120.2 | C35—C36—H36 | 120.3 |
C9—C14—H14 | 120.2 | C31—C36—H36 | 120.3 |
C15—C16—H161 | 109.5 | C37—C38—H381 | 109.5 |
C15—C16—H162 | 109.5 | C37—C38—H382 | 109.5 |
H161—C16—H162 | 109.5 | H381—C38—H382 | 109.5 |
C15—C16—H163 | 109.5 | C37—C38—H383 | 109.5 |
H161—C16—H163 | 109.5 | H381—C38—H383 | 109.5 |
H162—C16—H163 | 109.5 | H382—C38—H383 | 109.5 |
C19—C18—H18 | 119.6 | C39—C40—H40 | 120.0 |
C17—C18—H18 | 119.6 | C41—C40—H40 | 120.0 |
C20—C19—H19 | 120.5 | C42—C41—H41 | 120.5 |
C18—C19—H19 | 120.5 | C40—C41—H41 | 120.5 |
C20—C21—H21 | 120.6 | C42—C43—H43 | 120.1 |
C22—C21—H21 | 120.6 | C44—C43—H43 | 120.1 |
C17—C22—H22 | 120.5 | C39—C44—H44 | 121.0 |
C21—C22—H22 | 120.5 | C43—C44—H44 | 121.0 |
S1—C1—C2—O3 | 7.9 (8) | S2—C23—C24—O9 | 8.4 (8) |
S1—C1—N1—N2 | −1.3 (8) | S2—C23—N5—N6 | −4.6 (9) |
O1—S1—C1—C2 | 59.9 (5) | O7—S2—C23—C24 | 60.5 (5) |
O1—S1—C1—N1 | −117.4 (5) | O7—S2—C23—N5 | −117.9 (5) |
O2—S1—C1—C2 | −173.2 (5) | O8—S2—C23—C24 | −171.8 (5) |
O2—S1—C1—N1 | 9.4 (6) | O8—S2—C23—N5 | 9.8 (6) |
S1—C1—C2—C3 | −174.7 (5) | S2—C23—C24—C25 | −174.3 (4) |
N1—C1—C2—O3 | −174.5 (5) | N5—C23—C24—O9 | −173.1 (6) |
N1—C1—C2—C3 | 2.8 (9) | N5—C23—C24—C25 | 4.4 (9) |
N2—N1—C1—C2 | −178.7 (5) | N6—N5—C23—C24 | 177.0 (5) |
C1—N1—N2—C17 | 176.2 (5) | C23—N5—N6—C39 | 178.2 (6) |
C9—S1—C1—N1 | 124.9 (5) | C31—S2—C23—N5 | 124.1 (6) |
C9—S1—C1—C2 | −57.8 (5) | C31—S2—C23—C24 | −57.5 (5) |
C12—N3—C15—O4 | −2.0 (11) | C34—N7—C37—O10 | −1.0 (11) |
C12—N3—C15—C16 | 177.4 (6) | C34—N7—C37—C38 | 178.7 (6) |
O5—N4—C20—C19 | 6.5 (10) | O11—N8—C42—C41 | 2.8 (11) |
O5—N4—C20—C21 | −174.1 (7) | O11—N8—C42—C43 | −179.2 (8) |
O6—N4—C20—C19 | −174.5 (7) | O12—N8—C42—C41 | 179.6 (8) |
O6—N4—C20—C21 | 4.8 (10) | O12—N8—C42—C43 | −2.4 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.86 | 1.92 | 2.620 (6) | 138 |
N3—H3···O3i | 0.86 | 2.15 | 2.993 (6) | 166 |
N6—H61···O8 | 0.86 | 1.95 | 2.651 (7) | 138 |
N7—H71···O9ii | 0.86 | 2.14 | 2.980 (7) | 167 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C22H18N4O6S |
Mr | 466.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.461 (1), 11.663 (2), 24.621 (5) |
α, β, γ (°) | 94.31 (3), 90.88 (3), 94.01 (3) |
V (Å3) | 2130.7 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.78 |
Crystal size (mm) | 0.45 × 0.35 × 0.35 |
Data collection | |
Diffractometer | Kuma KM-4 diffractometer |
Absorption correction | ψ scan (XEMP; Siemens, 1989) |
Tmin, Tmax | 0.463, 0.537 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4490, 4354, 2363 |
Rint | 0.052 |
θmax (°) | 50.1 |
(sin θ/λ)max (Å−1) | 0.498 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.180, 1.07 |
No. of reflections | 4354 |
No. of parameters | 596 |
H-atom treatment | GEOM |
Δρmax, Δρmin (e Å−3) | 0.46, −0.25 |
Computer programs: KM-4 User's Guide (Kuma, 1991), KM-4 User's Guide), DATAPROC (Gałdecki et al., 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SYBYL (Tripos, 1996) and XP (Siemens, 1990), SHELXL97.
S1—O1 | 1.440 (5) | S2—O7 | 1.439 (5) |
S1—O2 | 1.445 (4) | S2—O8 | 1.448 (5) |
S1—C1 | 1.793 (6) | S2—C23 | 1.783 (6) |
S1—C9 | 1.732 (6) | S2—C31 | 1.749 (6) |
O3—C2 | 1.234 (6) | O9—C24 | 1.228 (7) |
N1—N2 | 1.311 (6) | N5—N6 | 1.305 (7) |
N1—C1 | 1.316 (7) | N5—C23 | 1.302 (7) |
N2—C17 | 1.400 (7) | N6—C39 | 1.411 (8) |
C1—C2 | 1.461 (8) | C23—C24 | 1.472 (8) |
C2—C3 | 1.493 (8) | C24—C25 | 1.491 (8) |
O5—N4 | 1.207 (8) | O11—N8 | 1.174 (7) |
O6—N4 | 1.211 (8) | O12—N8 | 1.208 (8) |
N4—C20 | 1.457 (8) | N8—C42 | 1.462 (8) |
N3—C12 | 1.396 (8) | N7—C34 | 1.407 (8) |
N3—C15 | 1.355 (8) | N7—C37 | 1.371 (8) |
O4—C15 | 1.209 (8) | O10—C37 | 1.200 (8) |
C15—C16 | 1.521 (9) | C37—C38 | 1.518 (9) |
S1···O3 | 2.916 (4) | S2···O9 | 2.926 (5) |
S1···N2 | 3.091 (5) | S2···N6 | 3.104 (6) |
O1···C2 | 3.230 (7) | O7···C24 | 3.218 (8) |
O2···C2 | 3.915 (7) | O8···C24 | 3.920 (8) |
O1—S1—O2 | 117.4 (3) | O7—S2—O8 | 118.3 (3) |
O1—S1—C1 | 109.3 (3) | O7—S2—C23 | 108.6 (3) |
O1—S1—C9 | 109.2 (3) | O7—S2—C31 | 109.7 (3) |
O2—S1—C1 | 105.2 (3) | O8—S2—C23 | 105.3 (3) |
O2—S1—C9 | 109.2 (3) | O8—S2—C31 | 107.8 (3) |
C1—S1—C9 | 105.5 (3) | C23—S2—C31 | 106.5 (3) |
N2—N1—C1 | 123.8 (5) | N6—N5—C23 | 124.4 (5) |
N1—N2—C17 | 119.9 (5) | N5—N6—C39 | 120.7 (6) |
N1—C1—C2 | 117.6 (5) | S2—C23—N5 | 125.8 (5) |
S1—C1—N1 | 124.7 (5) | S2—C23—C24 | 117.6 (5) |
S1—C1—C2 | 117.6 (4) | N5—C23—C24 | 116.6 (5) |
O3—C2—C1 | 117.8 (5) | O9—C24—C23 | 118.1 (6) |
O3—C2—C3 | 119.4 (5) | O9—C24—C25 | 119.1 (6) |
C1—C2—C3 | 122.8 (5) | C23—C24—C25 | 122.8 (5) |
O5—N4—O6 | 122.6 (7) | O11—N8—O12 | 122.2 (7) |
O5—N4—C20 | 117.8 (8) | O11—N8—C42 | 119.0 (7) |
O6—N4—C20 | 119.5 (7) | O12—N8—C42 | 118.7 (7) |
C12—N3—C15 | 128.7 (6) | C34—N7—C37 | 127.8 (6) |
O4—C15—N3 | 124.0 (7) | O10—C37—N7 | 123.7 (7) |
O4—C15—C16 | 121.7 (7) | O10—C37—C38 | 122.5 (7) |
N3—C15—C16 | 114.3 (6) | N7—C37—C38 | 113.8 (6) |
S1—C1—C2—O3 | 7.9 (8) | S2—C23—C24—O9 | 8.4 (8) |
S1—C1—N1—N2 | −1.3 (8) | S2—C23—N5—N6 | −4.6 (9) |
O1—S1—C1—C2 | 59.9 (5) | O7—S2—C23—C24 | 60.5 (5) |
O1—S1—C1—N1 | −117.4 (5) | O7—S2—C23—N5 | −117.9 (5) |
O2—S1—C1—C2 | −173.2 (5) | O8—S2—C23—C24 | −171.8 (5) |
O2—S1—C1—N1 | 9.4 (6) | O8—S2—C23—N5 | 9.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.86 | 1.92 | 2.620 (6) | 138 |
N3—H3···O3i | 0.86 | 2.15 | 2.993 (6) | 166 |
N6—H61···O8 | 0.86 | 1.95 | 2.651 (7) | 138 |
N7—H71···O9ii | 0.86 | 2.14 | 2.980 (7) | 167 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+2. |
The present work is part of a project aimed at structural studies of modified β-ketosulfones. The investigated compounds have bactericidal and fungicidal activity (Zakrzewski & Kacała, 1998; Zakrzewski, 1999). In this paper, the X-ray structure of 4'-{[benzoyl(4-nitrophenylhydrazono)methyl]sulfonyl}acetanilide, (I), is reported. The title compound, (I), shows a high rate of the photodynamic decay. Freshly grown crystals decompose within approximately two weeks of being exposed to daylight.
The solid-state conformation of all five α-phenylhydrazono-β-ketosulfones reported in the scientific literature (Wolf, 1999, 2001a,b) are constrained either by strong intramolecular resonance-assisted hydrogen bonds (abbreviated hereafter RAHB) (Jeffrey, 1997) or by non-stereospecific electrostatic attraction of the oppositely charged sulfonyl S and β-carbonyl C atoms. Electron-withdrawing terminal substituents linked to the α-phenylhydrazone group restrict the electron-density transfer from the hydrazone moiety towards the positively charged S and β-carbonyl C atoms. This effect strengthens the RAHB and prompts the simultaneous intensification of the intramolecular electrostatic attraction (Wolf, 2001a, and references therein).
Compound (I) crystallizes in the triclinic space group P1. Two complete molecules are located in the asymmetric unit. A view with the atom-numbering is shown in Fig. 1. The superposition of both independent molecules clearly reveals the high similarity of their conformations (Fig. 2). The root-mean-square deviation calculated from the least-squares fit of all respective non-H atoms is 0.23 Å.
In both independent molecules, one of the sulfonyl double bonds (S1═O2 and S2═O8), the β-carbonyl groups and the phenylhydrazone moieties are approximately coplanar. According to Bertolasi et al. (Bertolasi, Gilli et al., 1994; Bertolasi, Nanni et al., 1994), their configuration may be defined as EZE. The three letters indicate, relatively to the C═N bond, the positions of the carbonyl C═O and sulfonyl S═O double bond, as well as the N—C bond bearing the phenyl ring.
Central fragments of both molecules are fixed by the strong intramolecular RAHB's. These bonds connect the hydrazone and sulfonyl groups. The six-membered RAHB rings in both asymmetric molecules are practically planar; the root-mean-square deviations from the O2/S1/C1/N1/N2/H2 and O8/S2/C23/N5/N6/H61 planes are 0.05 and 0.04 Å, respectively. The intramolecular N2···O2 and N6···O8 distances [2.620 (6) and 2.651 (7) Å, respectively] are much shorter than the sum of respective van der Waals radii, 3.07 Å (Bondi, 1964).
Large positive atomic charges are located on atoms S1, S2, C2 and C24 (1.32, 1.31, 0.51 and 0.50 e, respectively). All O atoms are negatively charged. The atomic charges of O1, O2 and O3 range between -0.53 and -0.71 e. The electrostatic potential derived atomic charges were calculated, with GAUSSIAN98 (Frisch et al., 1998) at the RHF/6–311+G(d,p) level for the X-ray determined coordinates. Grid points were selected according to the CHELPG procedure of Breneman & Wiberg (1990). Electrostatic attraction of the oppositely loaded atoms generates intramolecular contacts beetwen S···O3 and O1···C2 pairs of atoms, details are summarized in Tables 2.
The bond-length distibution in (I) is close to that observed in all related compounds (Wolf, 1999, 2000, 2001a,b). In particular, the S1—C1 and S2—C23 bonds are longer [1.793 (6) and 1.783 (6) Å, respectively] than the conventional S—Csp2 single bond, 1.751 Å (Allen et al., 1992). Similar bond elongation in all α-phenylhydrazono-β-ketosulfones was explained by the hyperconjugative (Juaristi & Cuevas, 1995; Graczyk & Mikołajczyk, 1994; Cramer, 1996) interactions involving σ(S—C1) – π*(C═O3) bonding and non-bonding atomic orbitals. Similar intramolecular interactions were also observed in α-unsubstituted β-ketosulfones and β-ketosulfoxides (Distefano et al., 1991, 1996; Dal Colle et al., 1995; Olivato et al., 1998, 2000; Wolf, 2001c).
In the crystal lattice, molecules of (I) form elongated centrosymmetric dimers, which are connected by the intermolecular hydrogen bonds involving the β-carbonyl O3 and O7 atoms, and the N3—H3 and N7—H71 bonds of the terminal acetamide moieties (Fig 3). According to Etter's graph-set terminology (Etter et al., 1990; Bernstein et al., 1995), these bond systems can be described as R22(20).