The crystal structure of the title compound, C
21H
27NO
4S, confirms the presence of a monoalkylated sulfonamide group and that the propenyl group of the synthetic precursor has isomerized into the more thermodynamically favoured styrene. Analysis of the structure reveals that it is held together by a network of N—H
O, C—H
O=S and π–π interactions.
Supporting information
CCDC reference: 251738
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.135
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.33 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.74 Ratio
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C11
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A .. O3 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21 .. O4 .. 2.72 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
N-{3-Isopropoxy-4-methoxy-2-[(
E)-1-propenyl]benzyl}(phenyl)methanesulfonamide
top
Crystal data top
C21H27NO4S | F(000) = 832 |
Mr = 389.50 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 972 reflections |
a = 13.659 (2) Å | θ = 2.5–28.2° |
b = 16.160 (2) Å | µ = 0.18 mm−1 |
c = 9.5621 (14) Å | T = 173 K |
β = 102.561 (3)° | Prismic, colourless |
V = 2060.2 (5) Å3 | 0.48 × 0.32 × 0.27 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3500 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 27.0°, θmin = 1.5° |
φ and ω scans | h = −17→16 |
12803 measured reflections | k = −13→20 |
4483 independent reflections | l = −12→11 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0664P)2 + 1.128P] where P = (Fo2 + 2Fc2)/3 |
4483 reflections | (Δ/σ)max < 0.001 |
249 parameters | Δρmax = 0.81 e Å−3 |
0 restraints | Δρmin = −0.34 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 | |
S | 0.35696 (3) | −0.02424 (3) | 0.83788 (5) | 0.03037 (15) | |
N | 0.25280 (12) | −0.02030 (11) | 0.7215 (2) | 0.0353 (4) | |
H1 | 0.2248 | −0.0673 | 0.6875 | 0.042* | |
O1 | −0.15353 (10) | 0.13890 (9) | 0.49647 (14) | 0.0324 (3) | |
O2 | −0.21083 (11) | 0.04541 (11) | 0.69458 (17) | 0.0442 (4) | |
O3 | 0.35878 (11) | 0.04375 (10) | 0.93504 (16) | 0.0399 (4) | |
O4 | 0.36721 (11) | −0.10722 (10) | 0.89225 (18) | 0.0448 (4) | |
C1 | 0.09232 (14) | 0.05621 (13) | 0.6799 (2) | 0.0311 (4) | |
C2 | 0.01989 (14) | 0.10387 (12) | 0.5857 (2) | 0.0288 (4) | |
C3 | −0.08050 (14) | 0.09765 (12) | 0.5956 (2) | 0.0284 (4) | |
C4 | −0.10974 (14) | 0.04774 (14) | 0.6985 (2) | 0.0348 (5) | |
C5 | −0.03759 (16) | 0.00357 (16) | 0.7941 (2) | 0.0425 (5) | |
H5 | −0.0560 | −0.0292 | 0.8668 | 0.051* | |
C6 | 0.06206 (15) | 0.00775 (15) | 0.7821 (2) | 0.0387 (5) | |
H6 | 0.1109 | −0.0237 | 0.8463 | 0.046* | |
C7 | 0.20184 (14) | 0.05663 (13) | 0.6688 (2) | 0.0351 (5) | |
H7A | 0.2056 | 0.0648 | 0.5675 | 0.042* | |
H7B | 0.2367 | 0.1036 | 0.7249 | 0.042* | |
C8 | 0.04433 (17) | 0.16028 (15) | 0.4770 (3) | 0.0461 (6) | |
H8 | 0.0029 | 0.1581 | 0.3834 | 0.055* | |
C9 | 0.1214 (2) | 0.2150 (2) | 0.5004 (4) | 0.0710 (9) | |
H9 | 0.1664 | 0.2130 | 0.5913 | 0.085* | |
C10 | 0.1413 (3) | 0.2760 (3) | 0.4005 (5) | 0.1231 (19) | |
H10A | 0.2091 | 0.2679 | 0.3845 | 0.185* | |
H10B | 0.1358 | 0.3315 | 0.4394 | 0.185* | |
H10C | 0.0924 | 0.2701 | 0.3094 | 0.185* | |
C11 | −0.20249 (16) | 0.20851 (14) | 0.5524 (3) | 0.0398 (5) | |
H11 | −0.2104 | 0.1952 | 0.6515 | 0.048* | |
C12 | −0.1400 (2) | 0.28542 (17) | 0.5562 (4) | 0.0763 (10) | |
H12A | −0.0743 | 0.2767 | 0.6203 | 0.114* | |
H12B | −0.1739 | 0.3319 | 0.5914 | 0.114* | |
H12C | −0.1309 | 0.2978 | 0.4595 | 0.114* | |
C13 | −0.30385 (19) | 0.21659 (19) | 0.4551 (4) | 0.0706 (10) | |
H13A | −0.2963 | 0.2240 | 0.3562 | 0.106* | |
H13B | −0.3386 | 0.2646 | 0.4839 | 0.106* | |
H13C | −0.3430 | 0.1664 | 0.4613 | 0.106* | |
C14 | −0.24163 (19) | 0.0065 (2) | 0.8110 (3) | 0.0598 (8) | |
H14A | −0.2274 | −0.0529 | 0.8101 | 0.090* | |
H14B | −0.3138 | 0.0150 | 0.8021 | 0.090* | |
H14C | −0.2050 | 0.0306 | 0.9014 | 0.090* | |
C15 | 0.45748 (14) | −0.00933 (13) | 0.7478 (2) | 0.0323 (4) | |
H15A | 0.5220 | −0.0120 | 0.8189 | 0.039* | |
H15B | 0.4568 | −0.0550 | 0.6785 | 0.039* | |
C16 | 0.45144 (14) | 0.07166 (13) | 0.6695 (2) | 0.0313 (4) | |
C17 | 0.40238 (16) | 0.07679 (14) | 0.5256 (2) | 0.0376 (5) | |
H17 | 0.3760 | 0.0282 | 0.4752 | 0.045* | |
C18 | 0.39202 (18) | 0.15237 (16) | 0.4562 (3) | 0.0462 (6) | |
H18 | 0.3582 | 0.1555 | 0.3584 | 0.055* | |
C19 | 0.43051 (19) | 0.22346 (16) | 0.5281 (3) | 0.0495 (6) | |
H19 | 0.4222 | 0.2754 | 0.4805 | 0.059* | |
C20 | 0.48123 (19) | 0.21845 (15) | 0.6697 (3) | 0.0485 (6) | |
H20 | 0.5088 | 0.2671 | 0.7188 | 0.058* | |
C21 | 0.49225 (16) | 0.14291 (14) | 0.7406 (2) | 0.0394 (5) | |
H21 | 0.5276 | 0.1399 | 0.8377 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0205 (2) | 0.0378 (3) | 0.0326 (3) | −0.00169 (19) | 0.00541 (18) | 0.0007 (2) |
N | 0.0201 (8) | 0.0325 (9) | 0.0496 (11) | 0.0001 (7) | −0.0001 (7) | −0.0058 (8) |
O1 | 0.0269 (7) | 0.0362 (8) | 0.0311 (7) | 0.0115 (6) | −0.0001 (5) | −0.0049 (6) |
O2 | 0.0219 (7) | 0.0676 (11) | 0.0436 (9) | −0.0006 (7) | 0.0084 (6) | 0.0060 (8) |
O3 | 0.0342 (8) | 0.0532 (9) | 0.0336 (8) | −0.0050 (7) | 0.0101 (6) | −0.0074 (7) |
O4 | 0.0342 (8) | 0.0440 (9) | 0.0552 (10) | −0.0009 (7) | 0.0076 (7) | 0.0148 (8) |
C1 | 0.0221 (9) | 0.0336 (10) | 0.0360 (11) | 0.0015 (8) | 0.0031 (8) | −0.0017 (8) |
C2 | 0.0268 (9) | 0.0281 (10) | 0.0308 (10) | 0.0029 (7) | 0.0050 (7) | −0.0027 (8) |
C3 | 0.0238 (9) | 0.0310 (10) | 0.0284 (10) | 0.0047 (7) | 0.0011 (7) | −0.0039 (8) |
C4 | 0.0219 (9) | 0.0458 (12) | 0.0364 (11) | 0.0003 (8) | 0.0057 (8) | −0.0023 (9) |
C5 | 0.0305 (11) | 0.0563 (14) | 0.0407 (12) | −0.0009 (10) | 0.0078 (9) | 0.0148 (11) |
C6 | 0.0262 (10) | 0.0485 (13) | 0.0386 (11) | 0.0047 (9) | 0.0012 (8) | 0.0098 (10) |
C7 | 0.0238 (10) | 0.0368 (11) | 0.0442 (12) | 0.0023 (8) | 0.0064 (8) | 0.0024 (9) |
C8 | 0.0375 (12) | 0.0498 (14) | 0.0533 (14) | 0.0127 (10) | 0.0150 (10) | 0.0182 (11) |
C9 | 0.0585 (17) | 0.070 (2) | 0.090 (2) | 0.0029 (15) | 0.0283 (16) | 0.0302 (17) |
C10 | 0.092 (3) | 0.120 (4) | 0.152 (4) | −0.004 (3) | 0.016 (3) | 0.088 (3) |
C11 | 0.0339 (11) | 0.0391 (12) | 0.0448 (12) | 0.0128 (9) | 0.0051 (9) | −0.0116 (10) |
C12 | 0.0480 (16) | 0.0460 (16) | 0.130 (3) | 0.0035 (12) | 0.0085 (17) | −0.0338 (17) |
C13 | 0.0365 (13) | 0.0669 (18) | 0.097 (2) | 0.0225 (13) | −0.0108 (14) | −0.0366 (17) |
C14 | 0.0314 (12) | 0.103 (2) | 0.0468 (14) | −0.0138 (13) | 0.0123 (10) | 0.0072 (15) |
C15 | 0.0211 (9) | 0.0402 (11) | 0.0369 (11) | 0.0015 (8) | 0.0091 (8) | −0.0030 (9) |
C16 | 0.0219 (9) | 0.0405 (11) | 0.0340 (10) | −0.0021 (8) | 0.0121 (8) | −0.0041 (9) |
C17 | 0.0343 (11) | 0.0455 (13) | 0.0345 (11) | −0.0048 (9) | 0.0110 (9) | −0.0066 (9) |
C18 | 0.0452 (13) | 0.0594 (15) | 0.0349 (12) | −0.0026 (11) | 0.0108 (10) | 0.0057 (11) |
C19 | 0.0500 (14) | 0.0463 (14) | 0.0558 (15) | −0.0059 (11) | 0.0193 (12) | 0.0114 (11) |
C20 | 0.0490 (14) | 0.0440 (13) | 0.0533 (15) | −0.0142 (11) | 0.0132 (11) | −0.0033 (11) |
C21 | 0.0344 (11) | 0.0474 (13) | 0.0366 (11) | −0.0082 (9) | 0.0085 (9) | −0.0045 (10) |
Geometric parameters (Å, º) top
S—O4 | 1.4340 (16) | C10—H10C | 0.9800 |
S—O3 | 1.4356 (16) | C11—C13 | 1.497 (3) |
S—N | 1.6056 (17) | C11—C12 | 1.504 (4) |
S—C15 | 1.789 (2) | C11—H11 | 1.0000 |
N—C7 | 1.460 (3) | C12—H12A | 0.9800 |
N—H1 | 0.8800 | C12—H12B | 0.9800 |
O1—C3 | 1.388 (2) | C12—H12C | 0.9800 |
O1—C11 | 1.468 (2) | C13—H13A | 0.9800 |
O2—C4 | 1.374 (2) | C13—H13B | 0.9800 |
O2—C14 | 1.420 (3) | C13—H13C | 0.9800 |
C1—C6 | 1.384 (3) | C14—H14A | 0.9800 |
C1—C2 | 1.412 (3) | C14—H14B | 0.9800 |
C1—C7 | 1.523 (3) | C14—H14C | 0.9800 |
C2—C3 | 1.398 (3) | C15—C16 | 1.501 (3) |
C2—C8 | 1.475 (3) | C15—H15A | 0.9900 |
C3—C4 | 1.397 (3) | C15—H15B | 0.9900 |
C4—C5 | 1.387 (3) | C16—C21 | 1.391 (3) |
C5—C6 | 1.392 (3) | C16—C17 | 1.396 (3) |
C5—H5 | 0.9500 | C17—C18 | 1.383 (3) |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C7—H7A | 0.9900 | C18—C19 | 1.383 (4) |
C7—H7B | 0.9900 | C18—H18 | 0.9500 |
C8—C9 | 1.356 (4) | C19—C20 | 1.383 (4) |
C8—H8 | 0.9500 | C19—H19 | 0.9500 |
C9—C10 | 1.439 (4) | C20—C21 | 1.389 (3) |
C9—H9 | 0.9500 | C20—H20 | 0.9500 |
C10—H10A | 0.9800 | C21—H21 | 0.9500 |
C10—H10B | 0.9800 | | |
| | | |
O4—S—O3 | 119.63 (10) | O1—C11—C12 | 109.94 (19) |
O4—S—N | 106.87 (9) | C13—C11—C12 | 112.7 (2) |
O3—S—N | 107.82 (9) | O1—C11—H11 | 109.4 |
O4—S—C15 | 106.02 (10) | C13—C11—H11 | 109.4 |
O3—S—C15 | 107.56 (9) | C12—C11—H11 | 109.4 |
N—S—C15 | 108.55 (10) | C11—C12—H12A | 109.5 |
C7—N—S | 123.86 (14) | C11—C12—H12B | 109.5 |
C7—N—H1 | 118.1 | H12A—C12—H12B | 109.5 |
S—N—H1 | 118.1 | C11—C12—H12C | 109.5 |
C3—O1—C11 | 115.85 (15) | H12A—C12—H12C | 109.5 |
C4—O2—C14 | 117.26 (18) | H12B—C12—H12C | 109.5 |
C6—C1—C2 | 118.90 (18) | C11—C13—H13A | 109.5 |
C6—C1—C7 | 120.03 (18) | C11—C13—H13B | 109.5 |
C2—C1—C7 | 121.06 (18) | H13A—C13—H13B | 109.5 |
C3—C2—C1 | 118.62 (18) | C11—C13—H13C | 109.5 |
C3—C2—C8 | 117.88 (17) | H13A—C13—H13C | 109.5 |
C1—C2—C8 | 123.50 (18) | H13B—C13—H13C | 109.5 |
O1—C3—C4 | 119.04 (17) | O2—C14—H14A | 109.5 |
O1—C3—C2 | 119.29 (18) | O2—C14—H14B | 109.5 |
C4—C3—C2 | 121.60 (17) | H14A—C14—H14B | 109.5 |
O2—C4—C5 | 124.8 (2) | O2—C14—H14C | 109.5 |
O2—C4—C3 | 115.87 (18) | H14A—C14—H14C | 109.5 |
C5—C4—C3 | 119.36 (19) | H14B—C14—H14C | 109.5 |
C4—C5—C6 | 119.2 (2) | C16—C15—S | 113.14 (13) |
C4—C5—H5 | 120.4 | C16—C15—H15A | 109.0 |
C6—C5—H5 | 120.4 | S—C15—H15A | 109.0 |
C1—C6—C5 | 122.21 (19) | C16—C15—H15B | 109.0 |
C1—C6—H6 | 118.9 | S—C15—H15B | 109.0 |
C5—C6—H6 | 118.9 | H15A—C15—H15B | 107.8 |
N—C7—C1 | 111.97 (17) | C21—C16—C17 | 119.2 (2) |
N—C7—H7A | 109.2 | C21—C16—C15 | 120.35 (19) |
C1—C7—H7A | 109.2 | C17—C16—C15 | 120.40 (19) |
N—C7—H7B | 109.2 | C18—C17—C16 | 120.2 (2) |
C1—C7—H7B | 109.2 | C18—C17—H17 | 119.9 |
H7A—C7—H7B | 107.9 | C16—C17—H17 | 119.9 |
C9—C8—C2 | 125.0 (2) | C17—C18—C19 | 120.5 (2) |
C9—C8—H8 | 117.5 | C17—C18—H18 | 119.8 |
C2—C8—H8 | 117.5 | C19—C18—H18 | 119.8 |
C8—C9—C10 | 126.1 (3) | C20—C19—C18 | 119.6 (2) |
C8—C9—H9 | 117.0 | C20—C19—H19 | 120.2 |
C10—C9—H9 | 117.0 | C18—C19—H19 | 120.2 |
C9—C10—H10A | 109.5 | C19—C20—C21 | 120.5 (2) |
C9—C10—H10B | 109.5 | C19—C20—H20 | 119.7 |
H10A—C10—H10B | 109.5 | C21—C20—H20 | 119.7 |
C9—C10—H10C | 109.5 | C20—C21—C16 | 120.0 (2) |
H10A—C10—H10C | 109.5 | C20—C21—H21 | 120.0 |
H10B—C10—H10C | 109.5 | C16—C21—H21 | 120.0 |
O1—C11—C13 | 105.86 (17) | | |
| | | |
O4—S—N—C7 | 163.35 (17) | C4—C5—C6—C1 | 1.6 (4) |
O3—S—N—C7 | 33.5 (2) | S—N—C7—C1 | −128.48 (17) |
C15—S—N—C7 | −82.70 (19) | C6—C1—C7—N | 26.3 (3) |
C6—C1—C2—C3 | −2.6 (3) | C2—C1—C7—N | −152.81 (19) |
C7—C1—C2—C3 | 176.52 (18) | C3—C2—C8—C9 | 134.2 (3) |
C6—C1—C2—C8 | 177.3 (2) | C1—C2—C8—C9 | −45.7 (4) |
C7—C1—C2—C8 | −3.5 (3) | C2—C8—C9—C10 | −173.8 (3) |
C11—O1—C3—C4 | 71.6 (2) | C3—O1—C11—C13 | −153.9 (2) |
C11—O1—C3—C2 | −111.5 (2) | C3—O1—C11—C12 | 84.0 (3) |
C1—C2—C3—O1 | −174.87 (17) | O4—S—C15—C16 | 173.47 (14) |
C8—C2—C3—O1 | 5.2 (3) | O3—S—C15—C16 | −57.45 (17) |
C1—C2—C3—C4 | 2.0 (3) | N—S—C15—C16 | 58.96 (17) |
C8—C2—C3—C4 | −177.9 (2) | S—C15—C16—C21 | 86.1 (2) |
C14—O2—C4—C5 | 11.3 (3) | S—C15—C16—C17 | −92.1 (2) |
C14—O2—C4—C3 | −170.0 (2) | C21—C16—C17—C18 | −1.9 (3) |
O1—C3—C4—O2 | −1.5 (3) | C15—C16—C17—C18 | 176.31 (19) |
C2—C3—C4—O2 | −178.42 (18) | C16—C17—C18—C19 | 0.3 (3) |
O1—C3—C4—C5 | 177.28 (19) | C17—C18—C19—C20 | 1.2 (4) |
C2—C3—C4—C5 | 0.4 (3) | C18—C19—C20—C21 | −1.1 (4) |
O2—C4—C5—C6 | 176.5 (2) | C19—C20—C21—C16 | −0.5 (4) |
C3—C4—C5—C6 | −2.2 (3) | C17—C16—C21—C20 | 2.0 (3) |
C2—C1—C6—C5 | 0.9 (3) | C15—C16—C21—C20 | −176.2 (2) |
C7—C1—C6—C5 | −178.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1···O1i | 0.88 | 2.15 | 2.937 (2) | 148 |
C13—H13B···O4ii | 0.98 | 2.46 | 3.396 (4) | 160 |
C15—H15A···O3iii | 0.99 | 2.61 | 3.535 (4) | 157 |
C21—H21···O4iii | 0.95 | 2.72 | 3.662 (4) | 172 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, −y, −z+2. |