4-{5-[3,4-Di­methyl-5-(3,4,5-tri­methoxy­phenyl)­thio­phen-2-yl]-2-methoxyphenyl}morpholine

The title compound, C₂₆H₃₁NO₅S, was synthesized by the palladium-catalyzed coupling reaction of 2-(3-bromo-4-methoxy­phenyl)-3,4-di­methyl-5-(3,4,5-tri­methoxy­phenyl)­thio­phene and morpholine. This mol­ecule is composed of four rings. Two benzene rings are linked by a thio­phene moiety which is planar. The morpholine group has a chair conform­ation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.119
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

4-{2-Methoxy-5-[3,4-dimethyl-5-(3,4,5-trimethoxyphenyl)thiophen-2- yl]phenyl}morpholine

Crystal data

C26H31NO5S	F(000) = 1000
Mr = 469.59	Dx = 1.261 Mg m^−3
Monoclinic, P21/n	Melting point: 411 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.434 (4) Å	Cell parameters from 886 reflections
b = 7.820 (3) Å	θ = 3.2–25.3°
c = 27.782 (10) Å	µ = 0.17 mm^−1
β = 95.306 (6)°	T = 293 K
V = 2473.5 (16) Å^3	Block, colorless
Z = 4	0.26 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5073 independent reflections
Radiation source: fine-focus sealed tube	3223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.926, Tmax = 0.970	k = −4→9
13795 measured reflections	l = −34→32

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) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.8247P] where P = (Fo^2 + 2Fc^2)/3
5073 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.20 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	0.08599 (5)	0.67366 (8)	0.16195 (2)	0.04534 (18)
O1	0.18254 (16)	1.3050 (2)	0.24303 (7)	0.0626 (5)
O2	−0.00141 (16)	1.3596 (2)	0.29528 (7)	0.0701 (6)
O3	−0.18621 (16)	1.1465 (2)	0.28842 (7)	0.0706 (6)
O4	0.25392 (13)	−0.0238 (2)	0.05070 (6)	0.0533 (4)
O5	0.62077 (16)	0.3183 (3)	0.05887 (10)	0.0962 (8)
N1	0.38483 (15)	0.2558 (2)	0.07660 (7)	0.0446 (5)
C1	0.0810 (2)	1.0697 (3)	0.20016 (8)	0.0451 (6)
H1	0.1430	1.0523	0.1812	0.054*
C2	0.0885 (2)	1.1984 (3)	0.23464 (9)	0.0469 (6)
C3	−0.0033 (2)	1.2242 (3)	0.26315 (9)	0.0508 (6)
C4	−0.1015 (2)	1.1175 (3)	0.25759 (9)	0.0511 (6)
C5	−0.1091 (2)	0.9899 (3)	0.22262 (9)	0.0479 (6)
H5	−0.1752	0.9202	0.2187	0.057*
C6	−0.01785 (19)	0.9667 (3)	0.19359 (8)	0.0406 (5)
C7	0.2829 (2)	1.2681 (4)	0.21764 (10)	0.0691 (8)
H7A	0.3104	1.1547	0.2256	0.104*
H7B	0.3441	1.3490	0.2268	0.104*
H7C	0.2616	1.2759	0.1835	0.104*
C8	0.0653 (3)	1.3371 (4)	0.33953 (10)	0.0805 (9)
H8A	0.0292	1.2518	0.3581	0.121*
H8B	0.0695	1.4433	0.3570	0.121*
H8C	0.1431	1.3010	0.3339	0.121*
C9	−0.2846 (3)	1.0340 (4)	0.28475 (12)	0.0843 (10)
H9A	−0.3262	1.0446	0.2533	0.126*
H9B	−0.3360	1.0633	0.3089	0.126*
H9C	−0.2580	0.9184	0.2896	0.126*
C10	−0.02287 (18)	0.8268 (3)	0.15769 (8)	0.0387 (5)
C11	−0.10453 (18)	0.7940 (3)	0.11943 (8)	0.0376 (5)
C12	−0.07683 (17)	0.6448 (3)	0.09282 (7)	0.0357 (5)
C13	0.02340 (18)	0.5647 (3)	0.11180 (7)	0.0374 (5)
C14	−0.2106 (2)	0.9035 (3)	0.10616 (9)	0.0572 (7)
H14A	−0.2802	0.8423	0.1127	0.086*
H14B	−0.2146	0.9314	0.0724	0.086*
H14C	−0.2049	1.0069	0.1249	0.086*
C15	−0.1468 (2)	0.5916 (3)	0.04656 (8)	0.0527 (6)
H15A	−0.1013	0.5135	0.0292	0.079*
H15B	−0.1656	0.6907	0.0270	0.079*
H15C	−0.2181	0.5367	0.0540	0.079*
C16	0.08131 (18)	0.4102 (3)	0.09540 (7)	0.0367 (5)
C17	0.01827 (19)	0.2635 (3)	0.08240 (8)	0.0440 (6)
H17	−0.0626	0.2622	0.0841	0.053*
C18	0.07361 (19)	0.1190 (3)	0.06700 (8)	0.0429 (6)
H18	0.0294	0.0223	0.0581	0.052*
C19	0.19379 (19)	0.1161 (3)	0.06467 (8)	0.0392 (5)
C20	0.26089 (17)	0.2628 (3)	0.07787 (7)	0.0372 (5)
C21	0.20288 (18)	0.4055 (3)	0.09279 (7)	0.0380 (5)
H21	0.2466	0.5028	0.1015	0.046*
C22	0.1879 (2)	−0.1700 (3)	0.03524 (12)	0.0672 (8)
H22A	0.1451	−0.2105	0.0611	0.101*
H22B	0.2400	−0.2581	0.0261	0.101*
H22C	0.1338	−0.1407	0.0080	0.101*
C23	0.4246 (2)	0.2382 (4)	0.02854 (10)	0.0570 (7)
H23A	0.4131	0.3451	0.0110	0.068*
H23B	0.3793	0.1503	0.0107	0.068*
C24	0.5523 (2)	0.1913 (4)	0.03305 (13)	0.0848 (10)
H24A	0.5630	0.0827	0.0497	0.102*
H24B	0.5788	0.1783	0.0011	0.102*
C25	0.5820 (2)	0.3403 (5)	0.10521 (14)	0.0879 (11)
H25A	0.6285	0.4289	0.1223	0.105*
H25B	0.5943	0.2349	0.1234	0.105*
C26	0.4534 (2)	0.3888 (4)	0.10298 (10)	0.0619 (7)
H26A	0.4293	0.3995	0.1354	0.074*
H26B	0.4407	0.4979	0.0867	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0408 (3)	0.0513 (4)	0.0425 (3)	0.0069 (3)	−0.0036 (2)	−0.0132 (3)
O1	0.0685 (11)	0.0516 (11)	0.0657 (12)	−0.0152 (9)	−0.0044 (9)	−0.0106 (9)
O2	0.0824 (13)	0.0518 (11)	0.0719 (13)	0.0165 (10)	−0.0157 (10)	−0.0268 (10)
O3	0.0604 (11)	0.0732 (13)	0.0795 (14)	0.0048 (10)	0.0142 (10)	−0.0362 (11)
O4	0.0460 (9)	0.0391 (10)	0.0760 (12)	−0.0009 (8)	0.0127 (8)	−0.0133 (9)
O5	0.0452 (11)	0.1027 (18)	0.145 (2)	−0.0199 (11)	0.0317 (13)	−0.0432 (16)
N1	0.0328 (10)	0.0458 (12)	0.0552 (13)	−0.0022 (9)	0.0041 (9)	−0.0119 (10)
C1	0.0470 (13)	0.0418 (14)	0.0455 (14)	0.0013 (11)	−0.0017 (10)	−0.0017 (11)
C2	0.0527 (14)	0.0349 (13)	0.0502 (14)	−0.0001 (11)	−0.0105 (12)	−0.0002 (11)
C3	0.0589 (16)	0.0372 (14)	0.0537 (16)	0.0099 (12)	−0.0094 (12)	−0.0125 (11)
C4	0.0513 (14)	0.0480 (15)	0.0539 (15)	0.0125 (12)	0.0050 (12)	−0.0117 (12)
C5	0.0453 (13)	0.0431 (14)	0.0552 (15)	0.0015 (11)	0.0043 (11)	−0.0113 (12)
C6	0.0422 (12)	0.0363 (13)	0.0424 (13)	0.0058 (10)	−0.0014 (10)	−0.0049 (10)
C7	0.0717 (19)	0.085 (2)	0.0495 (16)	−0.0330 (17)	0.0006 (14)	−0.0060 (15)
C8	0.105 (2)	0.078 (2)	0.0567 (19)	0.0080 (19)	−0.0057 (17)	−0.0154 (16)
C9	0.068 (2)	0.096 (2)	0.094 (2)	−0.0043 (19)	0.0309 (17)	−0.037 (2)
C10	0.0377 (12)	0.0376 (13)	0.0412 (13)	0.0004 (10)	0.0066 (10)	−0.0012 (10)
C11	0.0350 (11)	0.0386 (13)	0.0394 (12)	−0.0039 (10)	0.0047 (9)	0.0031 (10)
C12	0.0327 (11)	0.0418 (13)	0.0328 (11)	−0.0082 (10)	0.0041 (9)	0.0010 (10)
C13	0.0371 (12)	0.0425 (13)	0.0332 (12)	−0.0065 (10)	0.0064 (9)	−0.0041 (10)
C14	0.0479 (14)	0.0554 (16)	0.0664 (18)	0.0069 (12)	−0.0045 (12)	−0.0008 (14)
C15	0.0497 (14)	0.0588 (16)	0.0476 (15)	−0.0044 (12)	−0.0059 (11)	−0.0058 (13)
C16	0.0383 (12)	0.0411 (13)	0.0311 (11)	−0.0019 (10)	0.0051 (9)	−0.0046 (10)
C17	0.0361 (12)	0.0509 (15)	0.0460 (14)	−0.0052 (11)	0.0091 (10)	−0.0050 (11)
C18	0.0411 (13)	0.0394 (13)	0.0492 (14)	−0.0095 (11)	0.0089 (10)	−0.0056 (11)
C19	0.0424 (12)	0.0383 (13)	0.0377 (12)	−0.0002 (10)	0.0080 (10)	−0.0018 (10)
C20	0.0353 (12)	0.0421 (13)	0.0345 (12)	−0.0027 (10)	0.0043 (9)	−0.0033 (10)
C21	0.0389 (12)	0.0383 (13)	0.0365 (12)	−0.0050 (10)	0.0022 (9)	−0.0076 (10)
C22	0.0640 (17)	0.0378 (15)	0.103 (2)	−0.0092 (13)	0.0251 (16)	−0.0130 (15)
C23	0.0484 (14)	0.0596 (17)	0.0656 (18)	−0.0042 (13)	0.0197 (13)	−0.0134 (14)
C24	0.0462 (16)	0.088 (2)	0.124 (3)	−0.0101 (16)	0.0311 (17)	−0.041 (2)
C25	0.0432 (16)	0.094 (3)	0.124 (3)	−0.0116 (17)	−0.0045 (17)	−0.035 (2)
C26	0.0439 (14)	0.0671 (19)	0.0746 (19)	−0.0082 (13)	0.0049 (13)	−0.0212 (15)

Geometric parameters (Å, º)

S1—C10	1.723 (2)	C11—C12	1.432 (3)
S1—C13	1.731 (2)	C11—C14	1.503 (3)
O1—C2	1.364 (3)	C12—C13	1.368 (3)
O1—C7	1.431 (3)	C12—C15	1.508 (3)
O2—C3	1.384 (3)	C13—C16	1.470 (3)
O2—C8	1.397 (3)	C14—H14A	0.9600
O3—C4	1.370 (3)	C14—H14B	0.9600
O3—C9	1.425 (3)	C14—H14C	0.9600
O4—C19	1.367 (3)	C15—H15A	0.9600
O4—C22	1.415 (3)	C15—H15B	0.9600
O5—C25	1.410 (4)	C15—H15C	0.9600
O5—C24	1.418 (3)	C16—C17	1.385 (3)
N1—C20	1.422 (3)	C16—C21	1.399 (3)
N1—C23	1.457 (3)	C17—C18	1.382 (3)
N1—C26	1.459 (3)	C17—H17	0.9300
C1—C2	1.386 (3)	C18—C19	1.382 (3)
C1—C6	1.386 (3)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.410 (3)
C2—C3	1.387 (3)	C20—C21	1.382 (3)
C3—C4	1.396 (3)	C21—H21	0.9300
C4—C5	1.390 (3)	C22—H22A	0.9600
C5—C6	1.389 (3)	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—C10	1.478 (3)	C23—C24	1.500 (3)
C7—H7A	0.9600	C23—H23A	0.9700
C7—H7B	0.9600	C23—H23B	0.9700
C7—H7C	0.9600	C24—H24A	0.9700
C8—H8A	0.9600	C24—H24B	0.9700
C8—H8B	0.9600	C25—C26	1.514 (3)
C8—H8C	0.9600	C25—H25A	0.9700
C9—H9A	0.9600	C25—H25B	0.9700
C9—H9B	0.9600	C26—H26A	0.9700
C9—H9C	0.9600	C26—H26B	0.9700
C10—C11	1.372 (3)
C10—S1—C13	92.54 (11)	H14A—C14—H14B	109.5
C2—O1—C7	116.6 (2)	C11—C14—H14C	109.5
C3—O2—C8	116.5 (2)	H14A—C14—H14C	109.5
C4—O3—C9	116.9 (2)	H14B—C14—H14C	109.5
C19—O4—C22	117.69 (18)	C12—C15—H15A	109.5
C25—O5—C24	110.0 (2)	C12—C15—H15B	109.5
C20—N1—C23	115.02 (18)	H15A—C15—H15B	109.5
C20—N1—C26	116.81 (18)	C12—C15—H15C	109.5
C23—N1—C26	109.19 (19)	H15A—C15—H15C	109.5
C2—C1—C6	120.7 (2)	H15B—C15—H15C	109.5
C2—C1—H1	119.7	C17—C16—C21	117.4 (2)
C6—C1—H1	119.7	C17—C16—C13	121.54 (19)
O1—C2—C1	124.0 (2)	C21—C16—C13	121.05 (19)
O1—C2—C3	116.1 (2)	C18—C17—C16	121.1 (2)
C1—C2—C3	119.9 (2)	C18—C17—H17	119.5
O2—C3—C2	120.8 (2)	C16—C17—H17	119.5
O2—C3—C4	119.6 (2)	C19—C18—C17	120.9 (2)
C2—C3—C4	119.6 (2)	C19—C18—H18	119.5
O3—C4—C5	123.6 (2)	C17—C18—H18	119.5
O3—C4—C3	116.1 (2)	O4—C19—C18	123.7 (2)
C5—C4—C3	120.3 (2)	O4—C19—C20	116.67 (18)
C6—C5—C4	119.8 (2)	C18—C19—C20	119.6 (2)
C6—C5—H5	120.1	C21—C20—C19	118.08 (19)
C4—C5—H5	120.1	C21—C20—N1	123.06 (19)
C1—C6—C5	119.7 (2)	C19—C20—N1	118.84 (19)
C1—C6—C10	119.9 (2)	C20—C21—C16	122.9 (2)
C5—C6—C10	120.3 (2)	C20—C21—H21	118.5
O1—C7—H7A	109.5	C16—C21—H21	118.5
O1—C7—H7B	109.5	O4—C22—H22A	109.5
H7A—C7—H7B	109.5	O4—C22—H22B	109.5
O1—C7—H7C	109.5	H22A—C22—H22B	109.5
H7A—C7—H7C	109.5	O4—C22—H22C	109.5
H7B—C7—H7C	109.5	H22A—C22—H22C	109.5
O2—C8—H8A	109.5	H22B—C22—H22C	109.5
O2—C8—H8B	109.5	N1—C23—C24	109.3 (2)
H8A—C8—H8B	109.5	N1—C23—H23A	109.8
O2—C8—H8C	109.5	C24—C23—H23A	109.8
H8A—C8—H8C	109.5	N1—C23—H23B	109.8
H8B—C8—H8C	109.5	C24—C23—H23B	109.8
O3—C9—H9A	109.5	H23A—C23—H23B	108.3
O3—C9—H9B	109.5	O5—C24—C23	111.0 (2)
H9A—C9—H9B	109.5	O5—C24—H24A	109.4
O3—C9—H9C	109.5	C23—C24—H24A	109.4
H9A—C9—H9C	109.5	O5—C24—H24B	109.4
H9B—C9—H9C	109.5	C23—C24—H24B	109.4
C11—C10—C6	129.9 (2)	H24A—C24—H24B	108.0
C11—C10—S1	111.04 (16)	O5—C25—C26	112.3 (3)
C6—C10—S1	119.03 (15)	O5—C25—H25A	109.1
C10—C11—C12	112.62 (19)	C26—C25—H25A	109.1
C10—C11—C14	124.0 (2)	O5—C25—H25B	109.1
C12—C11—C14	123.3 (2)	C26—C25—H25B	109.1
C13—C12—C11	113.03 (19)	H25A—C25—H25B	107.9
C13—C12—C15	124.2 (2)	N1—C26—C25	108.5 (2)
C11—C12—C15	122.6 (2)	N1—C26—H26A	110.0
C12—C13—C16	129.94 (19)	C25—C26—H26A	110.0
C12—C13—S1	110.75 (16)	N1—C26—H26B	110.0
C16—C13—S1	119.30 (16)	C25—C26—H26B	110.0
C11—C14—H14A	109.5	H26A—C26—H26B	108.4
C11—C14—H14B	109.5
C7—O1—C2—C1	−6.5 (3)	C15—C12—C13—C16	−4.3 (4)
C7—O1—C2—C3	173.4 (2)	C11—C12—C13—S1	−1.0 (2)
C6—C1—C2—O1	−179.7 (2)	C15—C12—C13—S1	174.52 (17)
C6—C1—C2—C3	0.4 (3)	C10—S1—C13—C12	0.24 (17)
C8—O2—C3—C2	−80.6 (3)	C10—S1—C13—C16	179.22 (17)
C8—O2—C3—C4	102.6 (3)	C12—C13—C16—C17	−46.0 (3)
O1—C2—C3—O2	4.8 (3)	S1—C13—C16—C17	135.28 (19)
C1—C2—C3—O2	−175.2 (2)	C12—C13—C16—C21	134.7 (2)
O1—C2—C3—C4	−178.4 (2)	S1—C13—C16—C21	−44.1 (3)
C1—C2—C3—C4	1.5 (4)	C21—C16—C17—C18	−0.7 (3)
C9—O3—C4—C5	2.2 (4)	C13—C16—C17—C18	180.0 (2)
C9—O3—C4—C3	−177.3 (2)	C16—C17—C18—C19	0.8 (3)
O2—C3—C4—O3	−5.9 (3)	C22—O4—C19—C18	3.7 (3)
C2—C3—C4—O3	177.3 (2)	C22—O4—C19—C20	−177.2 (2)
O2—C3—C4—C5	174.6 (2)	C17—C18—C19—O4	178.6 (2)
C2—C3—C4—C5	−2.2 (4)	C17—C18—C19—C20	−0.4 (3)
O3—C4—C5—C6	−178.5 (2)	O4—C19—C20—C21	−179.14 (19)
C3—C4—C5—C6	1.0 (4)	C18—C19—C20—C21	0.0 (3)
C2—C1—C6—C5	−1.6 (3)	O4—C19—C20—N1	−0.9 (3)
C2—C1—C6—C10	−178.1 (2)	C18—C19—C20—N1	178.2 (2)
C4—C5—C6—C1	0.9 (3)	C23—N1—C20—C21	−114.9 (2)
C4—C5—C6—C10	177.4 (2)	C26—N1—C20—C21	15.1 (3)
C1—C6—C10—C11	−124.7 (3)	C23—N1—C20—C19	67.0 (3)
C5—C6—C10—C11	58.8 (3)	C26—N1—C20—C19	−163.1 (2)
C1—C6—C10—S1	56.1 (3)	C19—C20—C21—C16	0.1 (3)
C5—C6—C10—S1	−120.5 (2)	N1—C20—C21—C16	−178.0 (2)
C13—S1—C10—C11	0.56 (17)	C17—C16—C21—C20	0.2 (3)
C13—S1—C10—C6	179.92 (18)	C13—C16—C21—C20	179.6 (2)
C6—C10—C11—C12	179.5 (2)	C20—N1—C23—C24	−166.7 (2)
S1—C10—C11—C12	−1.2 (2)	C26—N1—C23—C24	59.7 (3)
C6—C10—C11—C14	0.5 (4)	C25—O5—C24—C23	58.2 (4)
S1—C10—C11—C14	179.74 (18)	N1—C23—C24—O5	−59.7 (3)
C10—C11—C12—C13	1.4 (3)	C24—O5—C25—C26	−57.8 (4)
C14—C11—C12—C13	−179.5 (2)	C20—N1—C26—C25	169.3 (2)
C10—C11—C12—C15	−174.2 (2)	C23—N1—C26—C25	−58.0 (3)
C14—C11—C12—C15	4.9 (3)	O5—C25—C26—N1	57.9 (3)
C11—C12—C13—C16	−179.8 (2)