Molecules of the title compound, C
13H
15NO
3S, are linked into layers parallel to the
bc plane by C—H
O hydrogen bonds.
Supporting information
CCDC reference: 627449
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C)= 0.004 Å
- R factor = 0.060
- wR factor = 0.137
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
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No errors found in this datablock
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
N-allyl-
N-(
p-tolylsulfonyl)-acrylamide
top
Crystal data top
C13H15NO3S | F(000) = 560 |
Mr = 265.32 | Dx = 1.201 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2123 reflections |
a = 19.7925 (15) Å | θ = 2.1–24.6° |
b = 5.3686 (4) Å | µ = 0.22 mm−1 |
c = 14.5981 (11) Å | T = 291 K |
β = 108.937 (1)° | Block, colourless |
V = 1467.21 (19) Å3 | 0.30 × 0.26 × 0.24 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2879 independent reflections |
Radiation source: sealed tube | 2218 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −24→18 |
Tmin = 0.94, Tmax = 0.95 | k = −6→5 |
7569 measured reflections | l = −14→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.66P] where P = (Fo2 + 2Fc2)/3 |
2879 reflections | (Δ/σ)max = 0.001 |
164 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | |
C1 | 0.33600 (14) | 1.0015 (5) | 0.23041 (19) | 0.0369 (6) | |
C2 | 0.33661 (17) | 1.1138 (7) | 0.1449 (2) | 0.0526 (8) | |
H2 | 0.3090 | 1.2548 | 0.1220 | 0.063* | |
C3 | 0.37850 (17) | 1.0153 (6) | 0.0935 (2) | 0.0473 (7) | |
H3 | 0.3789 | 1.0904 | 0.0363 | 0.057* | |
C4 | 0.41980 (15) | 0.8046 (6) | 0.1277 (2) | 0.0433 (7) | |
C5 | 0.41919 (17) | 0.6924 (5) | 0.2133 (2) | 0.0483 (7) | |
H5 | 0.4468 | 0.5514 | 0.2361 | 0.058* | |
C6 | 0.37730 (14) | 0.7908 (6) | 0.2646 (2) | 0.0429 (7) | |
H6 | 0.3769 | 0.7157 | 0.3218 | 0.051* | |
C7 | 0.47061 (15) | 0.7100 (7) | 0.0767 (2) | 0.0503 (8) | |
H7A | 0.5086 | 0.6179 | 0.1217 | 0.076* | |
H7B | 0.4902 | 0.8488 | 0.0523 | 0.076* | |
H7C | 0.4451 | 0.6037 | 0.0240 | 0.076* | |
C8 | 0.23368 (15) | 0.7912 (6) | 0.3943 (2) | 0.0433 (7) | |
H8A | 0.2134 | 0.6273 | 0.3754 | 0.052* | |
H8B | 0.2841 | 0.7678 | 0.4293 | 0.052* | |
C9 | 0.19966 (14) | 0.8975 (5) | 0.46420 (19) | 0.0386 (6) | |
H9 | 0.2064 | 0.8282 | 0.5249 | 0.046* | |
C10 | 0.15785 (16) | 1.1049 (6) | 0.4316 (2) | 0.0513 (8) | |
H10A | 0.1524 | 1.1689 | 0.3704 | 0.062* | |
H10B | 0.1351 | 1.1811 | 0.4708 | 0.062* | |
C11 | 0.17085 (13) | 0.8684 (5) | 0.21307 (18) | 0.0344 (6) | |
C12 | 0.11192 (13) | 0.7174 (5) | 0.20909 (19) | 0.0356 (6) | |
H12 | 0.1149 | 0.5976 | 0.2563 | 0.043* | |
C13 | 0.05003 (15) | 0.7521 (6) | 0.1337 (2) | 0.0435 (7) | |
H13A | 0.0479 | 0.8727 | 0.0871 | 0.052* | |
H13B | 0.0101 | 0.6552 | 0.1291 | 0.052* | |
N1 | 0.22783 (12) | 0.9349 (5) | 0.30187 (17) | 0.0412 (6) | |
O1 | 0.33785 (11) | 1.1397 (4) | 0.39964 (15) | 0.0548 (6) | |
O2 | 0.25256 (12) | 1.3455 (5) | 0.25231 (16) | 0.0608 (6) | |
O3 | 0.17328 (9) | 0.9622 (4) | 0.13909 (14) | 0.0491 (6) | |
S1 | 0.28928 (4) | 1.12984 (14) | 0.30086 (5) | 0.0400 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0341 (13) | 0.0340 (15) | 0.0431 (14) | −0.0065 (11) | 0.0133 (11) | −0.0103 (12) |
C2 | 0.0536 (18) | 0.063 (2) | 0.0388 (15) | 0.0102 (16) | 0.0120 (13) | −0.0029 (14) |
C3 | 0.0613 (19) | 0.0419 (17) | 0.0421 (15) | −0.0020 (15) | 0.0214 (14) | 0.0022 (13) |
C4 | 0.0431 (15) | 0.0430 (17) | 0.0461 (16) | −0.0024 (13) | 0.0179 (13) | −0.0211 (13) |
C5 | 0.0570 (18) | 0.0256 (15) | 0.0610 (18) | 0.0093 (13) | 0.0175 (15) | −0.0121 (13) |
C6 | 0.0322 (13) | 0.0432 (17) | 0.0559 (17) | −0.0004 (12) | 0.0179 (12) | −0.0024 (13) |
C7 | 0.0323 (14) | 0.065 (2) | 0.0536 (17) | 0.0123 (14) | 0.0137 (13) | −0.0006 (15) |
C8 | 0.0440 (15) | 0.0427 (16) | 0.0429 (15) | 0.0148 (13) | 0.0140 (12) | 0.0036 (12) |
C9 | 0.0358 (13) | 0.0410 (16) | 0.0394 (14) | −0.0094 (12) | 0.0128 (11) | −0.0114 (12) |
C10 | 0.0550 (18) | 0.060 (2) | 0.0393 (15) | 0.0150 (16) | 0.0156 (13) | −0.0148 (14) |
C11 | 0.0315 (13) | 0.0350 (14) | 0.0407 (14) | 0.0081 (11) | 0.0171 (11) | 0.0018 (12) |
C12 | 0.0343 (13) | 0.0340 (14) | 0.0392 (14) | 0.0022 (11) | 0.0131 (11) | 0.0094 (11) |
C13 | 0.0434 (15) | 0.0433 (17) | 0.0398 (14) | 0.0108 (13) | 0.0078 (12) | −0.0119 (13) |
N1 | 0.0402 (13) | 0.0427 (14) | 0.0471 (13) | 0.0052 (10) | 0.0229 (10) | −0.0007 (10) |
O1 | 0.0505 (12) | 0.0479 (13) | 0.0554 (13) | −0.0145 (10) | 0.0026 (10) | −0.0232 (10) |
O2 | 0.0579 (13) | 0.0648 (16) | 0.0602 (14) | 0.0152 (12) | 0.0198 (11) | 0.0169 (12) |
O3 | 0.0295 (10) | 0.0640 (14) | 0.0506 (12) | −0.0103 (9) | 0.0089 (8) | 0.0194 (10) |
S1 | 0.0403 (4) | 0.0395 (4) | 0.0412 (4) | 0.0004 (3) | 0.0147 (3) | −0.0127 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.390 (4) | C8—H8A | 0.97 |
C1—C6 | 1.390 (4) | C8—H8B | 0.97 |
C1—S1 | 1.733 (3) | C9—C10 | 1.377 (4) |
C2—C3 | 1.390 (4) | C9—H9 | 0.93 |
C2—H2 | 0.93 | C10—H10A | 0.93 |
C3—C4 | 1.390 (4) | C10—H10B | 0.93 |
C3—H3 | 0.93 | C11—O3 | 1.207 (3) |
C4—C5 | 1.390 (4) | C11—C12 | 1.406 (4) |
C4—C7 | 1.520 (4) | C11—N1 | 1.460 (3) |
C5—C6 | 1.390 (4) | C12—C13 | 1.368 (4) |
C5—H5 | 0.93 | C12—H12 | 0.93 |
C6—H6 | 0.93 | C13—H13A | 0.93 |
C7—H7A | 0.96 | C13—H13B | 0.93 |
C7—H7B | 0.96 | N1—S1 | 1.608 (2) |
C7—H7C | 0.96 | O1—S1 | 1.451 (2) |
C8—C9 | 1.505 (4) | O2—S1 | 1.427 (2) |
C8—N1 | 1.526 (4) | | |
| | | |
C2—C1—C6 | 120.0 (3) | C9—C8—H8B | 107.6 |
C2—C1—S1 | 121.5 (2) | N1—C8—H8B | 107.6 |
C6—C1—S1 | 118.4 (2) | H8A—C8—H8B | 107.0 |
C1—C2—C3 | 120.0 (3) | C10—C9—C8 | 115.0 (3) |
C1—C2—H2 | 120.0 | C10—C9—H9 | 122.5 |
C3—C2—H2 | 120.0 | C8—C9—H9 | 122.5 |
C4—C3—C2 | 120.0 (3) | C9—C10—H10A | 120.0 |
C4—C3—H3 | 120.0 | C9—C10—H10B | 120.0 |
C2—C3—H3 | 120.0 | H10A—C10—H10B | 120.0 |
C3—C4—C5 | 120.0 (3) | O3—C11—C12 | 118.5 (2) |
C3—C4—C7 | 120.1 (3) | O3—C11—N1 | 116.7 (2) |
C5—C4—C7 | 119.7 (3) | C12—C11—N1 | 124.7 (2) |
C6—C5—C4 | 120.0 (3) | C13—C12—C11 | 118.0 (3) |
C6—C5—H5 | 120.0 | C13—C12—H12 | 121.0 |
C4—C5—H5 | 120.0 | C11—C12—H12 | 121.0 |
C5—C6—C1 | 120.0 (3) | C12—C13—H13A | 120.0 |
C5—C6—H6 | 120.0 | C12—C13—H13B | 120.0 |
C1—C6—H6 | 120.0 | H13A—C13—H13B | 120.0 |
C4—C7—H7A | 109.5 | C11—N1—C8 | 118.5 (2) |
C4—C7—H7B | 109.5 | C11—N1—S1 | 121.31 (18) |
H7A—C7—H7B | 109.5 | C8—N1—S1 | 119.77 (19) |
C4—C7—H7C | 109.5 | O2—S1—O1 | 122.01 (14) |
H7A—C7—H7C | 109.5 | O2—S1—N1 | 105.53 (14) |
H7B—C7—H7C | 109.5 | O1—S1—N1 | 105.89 (13) |
C9—C8—N1 | 119.1 (2) | O2—S1—C1 | 108.15 (14) |
C9—C8—H8A | 107.6 | O1—S1—C1 | 107.17 (13) |
N1—C8—H8A | 107.6 | N1—S1—C1 | 107.30 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.38 | 3.257 (4) | 156 |
C9—H9···O3ii | 0.93 | 2.52 | 3.374 (3) | 153 |
Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+3/2, z+1/2. |