2-Meth­oxy-4-[(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl­idene)meth­yl]­phenyl 4-methyl­benzene­sulfonate

Mol­ecules of the title compound, C₂₄H₁₉NO₆S, 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.

Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0655P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O6^i	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.