Molecules of the title compound, C
24H
19NO
6S, adopt the
Z configuration and have a distorted tetrahedral geometry around the S atom. The oxazolone, 2-phenyl and methoxyphenyl rings are approximately coplanar. The C atom between the methoxyphenyl and oxazolone rings displays a distorted trigonal bonding geometry. Pairs of molecules are linked into dimers through weak C—H
O hydrogen bonds.
Supporting information
CCDC reference: 645572
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-Methoxy-4-[(5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidene)methyl]phenyl
4-methylphenylsulfonate
top
Crystal data top
C24H19NO6S | Z = 2 |
Mr = 449.46 | F(000) = 468 |
Triclinic, P1 | Dx = 1.391 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7854 (7) Å | Cell parameters from 10980 reflections |
b = 10.2766 (11) Å | θ = 2.1–26.0° |
c = 16.0242 (15) Å | µ = 0.19 mm−1 |
α = 101.338 (8)° | T = 293 K |
β = 94.775 (8)° | Needle, orange |
γ = 99.492 (8)° | 0.48 × 0.15 × 0.05 mm |
V = 1072.82 (19) Å3 | |
Data collection top
Stoe IPDS-2 diffractometer | 4206 independent reflections |
Radiation source: fine-focus sealed tube | 2745 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
rotation method scans | h = −8→8 |
Absorption correction: integration | k = −12→12 |
Tmin = 0.913, Tmax = 0.990 | l = −19→19 |
9923 measured reflections | |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0655P)2] where P = (Fo2 + 2Fc2)/3 |
4206 reflections | (Δ/σ)max = 0.003 |
290 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.30 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 | |
S1 | 1.29957 (10) | 0.66402 (7) | 0.32696 (4) | 0.0530 (2) | |
O1 | 1.1203 (3) | 0.7162 (2) | 0.31612 (14) | 0.0707 (6) | |
O2 | 1.4398 (3) | 0.7151 (2) | 0.40157 (11) | 0.0712 (6) | |
O3 | 1.2439 (2) | 0.50631 (19) | 0.32655 (10) | 0.0510 (4) | |
O4 | 0.9025 (2) | 0.4826 (2) | 0.39867 (10) | 0.0568 (5) | |
O5 | 0.0760 (3) | −0.0186 (2) | 0.17185 (11) | 0.0604 (5) | |
O6 | 0.2011 (3) | −0.0574 (3) | 0.04480 (12) | 0.0784 (7) | |
N1 | 0.3301 (3) | 0.1362 (2) | 0.25366 (12) | 0.0530 (5) | |
C1 | 1.3347 (4) | 0.6999 (3) | 0.16492 (18) | 0.0651 (8) | |
H1 | 1.2066 | 0.7209 | 0.1646 | 0.078* | |
C2 | 1.4368 (5) | 0.7012 (4) | 0.09410 (19) | 0.0760 (9) | |
H2 | 1.3762 | 0.7239 | 0.0461 | 0.091* | |
C3 | 1.6271 (4) | 0.6696 (3) | 0.09266 (17) | 0.0645 (8) | |
C4 | 1.7129 (4) | 0.6370 (4) | 0.16481 (18) | 0.0687 (8) | |
H4 | 1.8402 | 0.6145 | 0.1650 | 0.082* | |
C5 | 1.6156 (4) | 0.6368 (3) | 0.23640 (17) | 0.0619 (7) | |
H5 | 1.6777 | 0.6165 | 0.2850 | 0.074* | |
C6 | 1.4252 (4) | 0.6670 (3) | 0.23591 (15) | 0.0479 (6) | |
C7 | 1.7383 (6) | 0.6747 (5) | 0.0155 (2) | 0.0956 (12) | |
H7A | 1.6455 | 0.6407 | −0.0358 | 0.143* | |
H7B | 1.8404 | 0.6203 | 0.0160 | 0.143* | |
H7C | 1.7998 | 0.7664 | 0.0170 | 0.143* | |
C8 | 1.0672 (4) | 0.4275 (3) | 0.27784 (14) | 0.0462 (6) | |
C9 | 1.0740 (4) | 0.3604 (3) | 0.19517 (15) | 0.0530 (6) | |
H9 | 1.1914 | 0.3746 | 0.1695 | 0.064* | |
C10 | 0.9064 (4) | 0.2724 (3) | 0.15071 (15) | 0.0556 (7) | |
H10 | 0.9103 | 0.2278 | 0.0946 | 0.067* | |
C11 | 0.7307 (4) | 0.2496 (3) | 0.18934 (14) | 0.0501 (6) | |
C12 | 0.7265 (4) | 0.3201 (3) | 0.27343 (14) | 0.0491 (6) | |
H12 | 0.6095 | 0.3060 | 0.2994 | 0.059* | |
C13 | 0.8925 (3) | 0.4095 (3) | 0.31802 (13) | 0.0460 (6) | |
C14 | 0.7296 (4) | 0.4603 (3) | 0.44316 (15) | 0.0595 (7) | |
H14A | 0.7555 | 0.5176 | 0.4994 | 0.089* | |
H14B | 0.7018 | 0.3675 | 0.4479 | 0.089* | |
H14C | 0.6157 | 0.4807 | 0.4120 | 0.089* | |
C15 | 0.5599 (4) | 0.1491 (3) | 0.14287 (15) | 0.0551 (7) | |
H15 | 0.5716 | 0.1131 | 0.0859 | 0.066* | |
C16 | 0.3884 (4) | 0.1021 (3) | 0.17160 (15) | 0.0529 (6) | |
C17 | 0.2233 (4) | 0.0023 (3) | 0.11840 (16) | 0.0576 (7) | |
C18 | 0.1535 (4) | 0.0662 (3) | 0.25011 (16) | 0.0527 (6) | |
C19 | 0.0275 (4) | 0.0699 (3) | 0.31908 (17) | 0.0572 (7) | |
C20 | −0.1704 (5) | 0.0005 (3) | 0.3049 (2) | 0.0704 (8) | |
H20 | −0.2228 | −0.0530 | 0.2513 | 0.085* | |
C21 | −0.2878 (6) | 0.0117 (4) | 0.3710 (3) | 0.0874 (11) | |
H21 | −0.4204 | −0.0343 | 0.3618 | 0.105* | |
C22 | −0.2112 (6) | 0.0901 (4) | 0.4504 (3) | 0.0902 (11) | |
H22 | −0.2921 | 0.0966 | 0.4946 | 0.108* | |
C23 | −0.0155 (6) | 0.1591 (4) | 0.4650 (2) | 0.0877 (11) | |
H23 | 0.0358 | 0.2123 | 0.5188 | 0.105* | |
C24 | 0.1038 (5) | 0.1491 (4) | 0.39950 (18) | 0.0723 (8) | |
H24 | 0.2362 | 0.1956 | 0.4092 | 0.087* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0540 (4) | 0.0539 (4) | 0.0488 (3) | 0.0038 (3) | 0.0176 (3) | 0.0061 (3) |
O1 | 0.0680 (12) | 0.0685 (15) | 0.0856 (13) | 0.0258 (11) | 0.0323 (10) | 0.0201 (11) |
O2 | 0.0737 (12) | 0.0763 (15) | 0.0490 (10) | −0.0122 (11) | 0.0109 (9) | −0.0006 (9) |
O3 | 0.0448 (9) | 0.0590 (12) | 0.0478 (9) | 0.0015 (8) | 0.0086 (7) | 0.0139 (8) |
O4 | 0.0499 (9) | 0.0715 (13) | 0.0385 (8) | −0.0067 (9) | 0.0133 (7) | −0.0016 (8) |
O5 | 0.0552 (10) | 0.0568 (12) | 0.0570 (10) | −0.0025 (9) | 0.0060 (8) | −0.0054 (9) |
O6 | 0.0743 (13) | 0.0900 (17) | 0.0509 (11) | −0.0002 (12) | 0.0024 (9) | −0.0176 (10) |
N1 | 0.0523 (12) | 0.0555 (14) | 0.0437 (10) | 0.0018 (10) | 0.0049 (9) | −0.0002 (9) |
C1 | 0.0594 (16) | 0.082 (2) | 0.0634 (16) | 0.0196 (15) | 0.0161 (13) | 0.0296 (15) |
C2 | 0.074 (2) | 0.104 (3) | 0.0573 (16) | 0.0153 (19) | 0.0113 (14) | 0.0336 (17) |
C3 | 0.0690 (18) | 0.069 (2) | 0.0535 (15) | 0.0005 (15) | 0.0226 (13) | 0.0119 (13) |
C4 | 0.0551 (16) | 0.088 (2) | 0.0681 (17) | 0.0168 (16) | 0.0226 (14) | 0.0195 (16) |
C5 | 0.0541 (15) | 0.082 (2) | 0.0565 (14) | 0.0159 (14) | 0.0149 (12) | 0.0257 (14) |
C6 | 0.0490 (13) | 0.0472 (15) | 0.0476 (12) | 0.0035 (11) | 0.0150 (10) | 0.0106 (11) |
C7 | 0.103 (3) | 0.115 (3) | 0.0697 (19) | 0.005 (2) | 0.0406 (19) | 0.022 (2) |
C8 | 0.0456 (12) | 0.0490 (15) | 0.0435 (11) | 0.0051 (11) | 0.0095 (10) | 0.0100 (10) |
C9 | 0.0506 (14) | 0.0622 (17) | 0.0458 (12) | 0.0069 (12) | 0.0175 (11) | 0.0089 (12) |
C10 | 0.0635 (15) | 0.0601 (17) | 0.0399 (11) | 0.0073 (13) | 0.0161 (11) | 0.0023 (11) |
C11 | 0.0556 (14) | 0.0511 (16) | 0.0410 (11) | 0.0072 (12) | 0.0084 (10) | 0.0046 (10) |
C12 | 0.0473 (13) | 0.0556 (16) | 0.0422 (11) | 0.0046 (11) | 0.0114 (10) | 0.0064 (11) |
C13 | 0.0477 (13) | 0.0527 (15) | 0.0359 (11) | 0.0068 (11) | 0.0094 (9) | 0.0057 (10) |
C14 | 0.0561 (15) | 0.079 (2) | 0.0391 (12) | 0.0038 (14) | 0.0179 (11) | 0.0056 (12) |
C15 | 0.0615 (15) | 0.0597 (17) | 0.0381 (11) | 0.0074 (13) | 0.0064 (11) | −0.0007 (11) |
C16 | 0.0531 (14) | 0.0555 (17) | 0.0444 (12) | 0.0077 (12) | 0.0034 (11) | 0.0004 (11) |
C17 | 0.0579 (15) | 0.0551 (17) | 0.0539 (14) | 0.0082 (13) | 0.0068 (12) | −0.0006 (12) |
C18 | 0.0558 (15) | 0.0456 (15) | 0.0526 (13) | 0.0076 (12) | 0.0045 (11) | 0.0027 (11) |
C19 | 0.0638 (16) | 0.0458 (16) | 0.0625 (15) | 0.0104 (13) | 0.0149 (12) | 0.0097 (12) |
C20 | 0.0740 (19) | 0.0544 (18) | 0.0799 (19) | 0.0028 (15) | 0.0239 (16) | 0.0084 (15) |
C21 | 0.086 (2) | 0.063 (2) | 0.113 (3) | 0.0001 (18) | 0.046 (2) | 0.014 (2) |
C22 | 0.114 (3) | 0.068 (2) | 0.097 (3) | 0.018 (2) | 0.060 (2) | 0.019 (2) |
C23 | 0.116 (3) | 0.078 (3) | 0.0648 (18) | 0.012 (2) | 0.0342 (19) | 0.0008 (16) |
C24 | 0.081 (2) | 0.068 (2) | 0.0622 (17) | 0.0048 (16) | 0.0180 (15) | 0.0027 (15) |
Geometric parameters (Å, º) top
S1—O1 | 1.419 (2) | C8—C13 | 1.398 (3) |
S1—O2 | 1.418 (2) | C9—C10 | 1.375 (4) |
S1—O3 | 1.601 (2) | C9—H9 | 0.9300 |
S1—C6 | 1.753 (2) | C10—C11 | 1.395 (4) |
O3—C8 | 1.407 (3) | C10—H10 | 0.9300 |
O4—C13 | 1.351 (3) | C11—C12 | 1.404 (3) |
O4—C14 | 1.432 (3) | C11—C15 | 1.457 (4) |
O5—C17 | 1.387 (3) | C12—C13 | 1.375 (3) |
O5—C18 | 1.385 (3) | C12—H12 | 0.9300 |
O6—C17 | 1.202 (3) | C14—H14A | 0.9600 |
N1—C16 | 1.400 (3) | C14—H14B | 0.9600 |
N1—C18 | 1.283 (3) | C14—H14C | 0.9600 |
C1—C2 | 1.379 (4) | C15—C16 | 1.339 (4) |
C1—C6 | 1.374 (4) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C17 | 1.467 (4) |
C2—C3 | 1.383 (4) | C18—C19 | 1.451 (4) |
C2—H2 | 0.9300 | C19—C24 | 1.389 (4) |
C3—C4 | 1.376 (4) | C19—C20 | 1.390 (4) |
C3—C7 | 1.507 (4) | C20—C21 | 1.376 (5) |
C4—C5 | 1.371 (4) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.374 (5) |
C5—C6 | 1.377 (4) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—C23 | 1.376 (5) |
C7—H7A | 0.9600 | C22—H22 | 0.9300 |
C7—H7B | 0.9600 | C23—C24 | 1.376 (5) |
C7—H7C | 0.9600 | C23—H23 | 0.9300 |
C8—C9 | 1.376 (3) | C24—H24 | 0.9300 |
| | | |
O1—S1—O2 | 120.99 (14) | C10—C11—C15 | 119.2 (2) |
O1—S1—O3 | 109.56 (12) | C12—C11—C15 | 121.8 (2) |
O2—S1—O3 | 103.03 (12) | C13—C12—C11 | 121.1 (2) |
O1—S1—C6 | 109.18 (13) | C13—C12—H12 | 119.5 |
O2—S1—C6 | 109.30 (12) | C11—C12—H12 | 119.5 |
O3—S1—C6 | 103.23 (11) | O4—C13—C12 | 125.4 (2) |
C8—O3—S1 | 119.98 (16) | O4—C13—C8 | 116.3 (2) |
C13—O4—C14 | 117.48 (19) | C12—C13—C8 | 118.3 (2) |
C17—O5—C18 | 105.00 (19) | O4—C14—H14A | 109.5 |
C18—N1—C16 | 105.8 (2) | O4—C14—H14B | 109.5 |
C2—C1—C6 | 119.0 (3) | H14A—C14—H14B | 109.5 |
C2—C1—H1 | 120.5 | O4—C14—H14C | 109.5 |
C6—C1—H1 | 120.5 | H14A—C14—H14C | 109.5 |
C1—C2—C3 | 121.7 (3) | H14B—C14—H14C | 109.5 |
C1—C2—H2 | 119.2 | C11—C15—C16 | 128.3 (2) |
C3—C2—H2 | 119.2 | C16—C15—H15 | 115.8 |
C2—C3—C4 | 117.7 (2) | C11—C15—H15 | 115.8 |
C2—C3—C7 | 120.9 (3) | C15—C16—N1 | 128.6 (2) |
C4—C3—C7 | 121.3 (3) | C15—C16—C17 | 123.8 (2) |
C5—C4—C3 | 121.7 (3) | N1—C16—C17 | 107.6 (2) |
C5—C4—H4 | 119.2 | O6—C17—O5 | 121.4 (3) |
C3—C4—H4 | 119.2 | O6—C17—C16 | 133.0 (3) |
C4—C5—C6 | 119.5 (3) | O5—C17—C16 | 105.6 (2) |
C4—C5—H5 | 120.2 | N1—C18—O5 | 116.0 (2) |
C6—C5—H5 | 120.2 | N1—C18—C19 | 126.3 (2) |
C1—C6—C5 | 120.4 (2) | O5—C18—C19 | 117.6 (2) |
C1—C6—S1 | 120.2 (2) | C24—C19—C20 | 119.7 (3) |
C5—C6—S1 | 119.4 (2) | C24—C19—C18 | 119.2 (3) |
C3—C7—H7A | 109.5 | C20—C19—C18 | 121.1 (3) |
C3—C7—H7B | 109.5 | C19—C20—C21 | 119.2 (3) |
H7A—C7—H7B | 109.5 | C19—C20—H20 | 120.4 |
C3—C7—H7C | 109.5 | C21—C20—H20 | 120.4 |
H7A—C7—H7C | 109.5 | C22—C21—C20 | 120.7 (3) |
H7B—C7—H7C | 109.5 | C22—C21—H21 | 119.6 |
C9—C8—C13 | 121.6 (2) | C20—C21—H21 | 119.6 |
C9—C8—O3 | 119.8 (2) | C23—C22—C21 | 120.4 (3) |
C13—C8—O3 | 118.4 (2) | C23—C22—H22 | 119.8 |
C8—C9—C10 | 119.7 (2) | C21—C22—H22 | 119.8 |
C8—C9—H9 | 120.1 | C22—C23—C24 | 119.7 (3) |
C10—C9—H9 | 120.1 | C22—C23—H23 | 120.2 |
C9—C10—C11 | 120.3 (2) | C24—C23—H23 | 120.2 |
C9—C10—H10 | 119.8 | C23—C24—C19 | 120.3 (3) |
C11—C10—H10 | 119.8 | C23—C24—H24 | 119.9 |
C10—C11—C12 | 119.0 (2) | C19—C24—H24 | 119.9 |
| | | |
O1—S1—O3—C8 | 31.07 (19) | C9—C8—C13—O4 | −178.8 (2) |
O2—S1—O3—C8 | 161.09 (16) | O3—C8—C13—O4 | 7.3 (4) |
C6—S1—O3—C8 | −85.14 (18) | C9—C8—C13—C12 | 1.4 (4) |
C6—C1—C2—C3 | 0.3 (5) | O3—C8—C13—C12 | −172.6 (2) |
C1—C2—C3—C4 | −0.3 (5) | C10—C11—C15—C16 | 172.0 (3) |
C1—C2—C3—C7 | −178.6 (4) | C12—C11—C15—C16 | −5.2 (5) |
C2—C3—C4—C5 | −0.7 (5) | C11—C15—C16—N1 | −0.7 (5) |
C7—C3—C4—C5 | 177.7 (3) | C11—C15—C16—C17 | 178.6 (3) |
C3—C4—C5—C6 | 1.5 (5) | C18—N1—C16—C15 | 179.4 (3) |
C2—C1—C6—C5 | 0.5 (5) | C18—N1—C16—C17 | 0.0 (3) |
C2—C1—C6—S1 | −179.9 (3) | C18—O5—C17—O6 | −179.9 (3) |
C4—C5—C6—C1 | −1.4 (5) | C18—O5—C17—C16 | 0.7 (3) |
C4—C5—C6—S1 | 179.0 (3) | C15—C16—C17—O6 | 0.9 (6) |
O1—S1—C6—C1 | −7.7 (3) | N1—C16—C17—O6 | −179.7 (3) |
O2—S1—C6—C1 | −142.1 (2) | C15—C16—C17—O5 | −180.0 (3) |
O3—S1—C6—C1 | 108.8 (2) | N1—C16—C17—O5 | −0.5 (3) |
O1—S1—C6—C5 | 171.9 (2) | C16—N1—C18—O5 | 0.6 (3) |
O2—S1—C6—C5 | 37.5 (3) | C16—N1—C18—C19 | −178.0 (3) |
O3—S1—C6—C5 | −71.6 (2) | C17—O5—C18—N1 | −0.9 (3) |
S1—O3—C8—C9 | 92.3 (3) | C17—O5—C18—C19 | 177.8 (3) |
S1—O3—C8—C13 | −93.6 (3) | N1—C18—C19—C24 | −4.4 (5) |
C13—C8—C9—C10 | −0.7 (4) | O5—C18—C19—C24 | 177.1 (3) |
O3—C8—C9—C10 | 173.2 (2) | N1—C18—C19—C20 | 172.7 (3) |
C8—C9—C10—C11 | −0.7 (4) | O5—C18—C19—C20 | −5.8 (4) |
C9—C10—C11—C12 | 1.4 (4) | C24—C19—C20—C21 | 0.2 (5) |
C9—C10—C11—C15 | −175.9 (3) | C18—C19—C20—C21 | −177.0 (3) |
C10—C11—C12—C13 | −0.6 (4) | C19—C20—C21—C22 | −0.2 (6) |
C15—C11—C12—C13 | 176.6 (3) | C20—C21—C22—C23 | 0.2 (6) |
C14—O4—C13—C12 | 3.4 (4) | C21—C22—C23—C24 | −0.1 (6) |
C14—O4—C13—C8 | −176.4 (2) | C22—C23—C24—C19 | 0.0 (6) |
C11—C12—C13—O4 | 179.4 (3) | C20—C19—C24—C23 | −0.1 (5) |
C11—C12—C13—C8 | −0.7 (4) | C18—C19—C24—C23 | 177.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O6i | 0.93 | 2.52 | 3.405 (3) | 158 |
C12—H12···N1 | 0.93 | 2.31 | 2.975 (4) | 128 |
Symmetry code: (i) −x+1, −y, −z. |