Methyl 3-(dimethyl­amino)-2-[2-(1-{3-[4-(methyl­sulfanyl)phenyl]-1,2,4-oxadiazol-5-yl}-2-(dimethyl­amino)vinyl­oxy)phenyl]acrylate

In the title compound, C₂₅H₂₈N₄O₄S, which is a derivative of 1,2,4-oxadiazole, there are intramolecular C—H...O and intermolecular C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.211
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C22
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C25 H28 N4 O4 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

Methyl 3-(dimethylamino)-2-[2-(1-{3-[4-(methylsulfanyl)phenyl]-1,2,4-oxadiazol-5-yl}- 2-(dimethylamino)vinyloxy)phenyl]acrylate

Crystal data

C25H28N4O4S	F(000) = 1016
Mr = 480.57	Dx = 1.298 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2940 (17) Å	Cell parameters from 25 reflections
b = 12.654 (3) Å	θ = 9–13°
c = 23.601 (5) Å	µ = 0.17 mm^−1
β = 97.02 (3)°	T = 293 K
V = 2458.4 (9) Å^3	Block, colourless
Z = 4	0.4 × 0.3 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.057
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.7°
Graphite monochromator	h = 0→9
ω/2θ scans	k = 0→15
5129 measured reflections	l = −28→28
4785 independent reflections	3 standard reflections every 200 reflections
2345 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.211	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.009
4785 reflections	Δρmax = 0.25 e Å^−3
308 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (13)

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
S	0.08012 (14)	0.17354 (10)	0.04616 (5)	0.0825 (4)
O1	0.4590 (4)	−0.3252 (2)	0.22705 (12)	0.0807 (9)
O2	0.7074 (3)	−0.2165 (2)	0.34968 (10)	0.0578 (7)
O3	0.7910 (4)	−0.1166 (3)	0.51887 (11)	0.0861 (10)
O4	0.9948 (3)	−0.1811 (2)	0.47539 (11)	0.0661 (8)
N1	0.3691 (5)	−0.2671 (3)	0.18243 (16)	0.0808 (11)
N2	0.5052 (3)	−0.1568 (3)	0.24706 (12)	0.0568 (8)
N3	0.6235 (4)	0.0744 (3)	0.38594 (14)	0.0639 (9)
N4	0.7353 (4)	−0.4533 (3)	0.36462 (15)	0.0729 (10)
C1	0.1268 (5)	0.2986 (3)	0.0787 (2)	0.0854 (14)
H1B	0.0736	0.3534	0.0552	0.128*
H1C	0.2421	0.3097	0.0827	0.128*
H1D	0.0897	0.3002	0.1156	0.128*
C2	0.1838 (4)	0.0809 (3)	0.09275 (16)	0.0611 (10)
C3	0.1782 (5)	−0.0239 (3)	0.07402 (17)	0.0677 (11)
H3A	0.1243	−0.0396	0.0381	0.081*
C4	0.2488 (4)	−0.1033 (3)	0.10662 (17)	0.0642 (11)
H4A	0.2425	−0.1722	0.0928	0.077*
C5	0.3314 (4)	−0.0827 (3)	0.16097 (15)	0.0561 (10)
C6	0.3389 (5)	0.0211 (3)	0.17948 (17)	0.0641 (11)
H6A	0.3940	0.0370	0.2152	0.077*
C7	0.2666 (4)	0.1014 (3)	0.14613 (16)	0.0628 (11)
H7A	0.2736	0.1704	0.1597	0.075*
C8	0.4031 (4)	−0.1697 (3)	0.19627 (16)	0.0566 (10)
C9	0.5356 (4)	−0.2537 (3)	0.26288 (16)	0.0565 (9)
C10	0.6370 (4)	−0.2939 (3)	0.31215 (16)	0.0558 (10)
C11	0.8484 (4)	−0.1667 (3)	0.33657 (14)	0.0454 (8)
C12	0.9251 (4)	−0.1944 (3)	0.28989 (14)	0.0558 (10)
H12A	0.8840	−0.2481	0.2654	0.067*
C13	1.0640 (5)	−0.1405 (3)	0.28045 (16)	0.0633 (11)
H13A	1.1171	−0.1586	0.2493	0.076*
C14	1.1245 (5)	−0.0616 (3)	0.31570 (18)	0.0682 (11)
H14A	1.2174	−0.0253	0.3085	0.082*
C15	1.0470 (5)	−0.0352 (3)	0.36264 (16)	0.0589 (10)
H15A	1.0901	0.0182	0.3870	0.071*
C16	0.9059 (4)	−0.0870 (3)	0.37406 (14)	0.0449 (8)
C17	0.8208 (4)	−0.0611 (3)	0.42423 (14)	0.0501 (9)
C18	0.8623 (5)	−0.1193 (3)	0.47689 (15)	0.0579 (10)
C19	1.0447 (6)	−0.2425 (4)	0.52581 (18)	0.0857 (14)
H19A	1.1395	−0.2829	0.5203	0.129*
H19B	0.9585	−0.2895	0.5329	0.129*
H19C	1.0693	−0.1961	0.5579	0.129*
C20	0.6985 (4)	0.0100 (3)	0.42550 (15)	0.0522 (9)
H20A	0.6596	0.0147	0.4607	0.063*
C21	0.4973 (6)	0.1459 (4)	0.3995 (2)	0.0966 (16)
H21A	0.4802	0.1368	0.4387	0.145*
H21B	0.3984	0.1309	0.3753	0.145*
H21C	0.5298	0.2175	0.3935	0.145*
C22	0.6621 (7)	0.0818 (4)	0.32782 (19)	0.0909 (15)
H22A	0.7469	0.0325	0.3224	0.136*
H22B	0.6978	0.1523	0.3207	0.136*
H22C	0.5672	0.0656	0.3018	0.136*
C23	0.6512 (5)	−0.3983 (3)	0.32260 (17)	0.0622 (10)
H23A	0.5910	−0.4402	0.2954	0.075*
C24	0.7202 (6)	−0.5682 (3)	0.3660 (2)	0.0888 (14)
H24A	0.6527	−0.5917	0.3324	0.133*
H24B	0.6721	−0.5888	0.3993	0.133*
H24C	0.8259	−0.5997	0.3671	0.133*
C25	0.8376 (5)	−0.4064 (4)	0.41265 (17)	0.0814 (13)
H25A	0.8407	−0.3311	0.4078	0.122*
H25B	0.9456	−0.4344	0.4143	0.122*
H25C	0.7939	−0.4226	0.4475	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0732 (8)	0.0890 (9)	0.0805 (8)	−0.0152 (7)	−0.0096 (6)	0.0062 (7)
O1	0.092 (2)	0.0659 (18)	0.078 (2)	−0.0055 (17)	−0.0154 (17)	−0.0138 (16)
O2	0.0485 (15)	0.0755 (17)	0.0518 (14)	−0.0105 (13)	0.0159 (12)	−0.0137 (13)
O3	0.087 (2)	0.126 (3)	0.0500 (16)	0.0136 (19)	0.0263 (15)	0.0080 (17)
O4	0.0631 (17)	0.0824 (19)	0.0540 (15)	0.0115 (15)	0.0117 (13)	0.0182 (14)
N1	0.089 (3)	0.072 (2)	0.075 (2)	−0.004 (2)	−0.015 (2)	−0.015 (2)
N2	0.0479 (18)	0.068 (2)	0.0538 (19)	−0.0057 (16)	0.0048 (15)	−0.0137 (16)
N3	0.058 (2)	0.068 (2)	0.067 (2)	0.0140 (17)	0.0149 (16)	−0.0007 (18)
N4	0.065 (2)	0.083 (3)	0.069 (2)	0.003 (2)	0.0014 (18)	−0.001 (2)
C1	0.081 (3)	0.088 (3)	0.089 (3)	−0.001 (3)	0.016 (3)	0.002 (3)
C2	0.039 (2)	0.080 (3)	0.065 (2)	−0.013 (2)	0.0112 (18)	−0.001 (2)
C3	0.064 (3)	0.082 (3)	0.056 (2)	−0.016 (2)	−0.001 (2)	−0.013 (2)
C4	0.052 (2)	0.076 (3)	0.065 (3)	−0.013 (2)	0.010 (2)	−0.014 (2)
C5	0.039 (2)	0.077 (3)	0.055 (2)	−0.0084 (19)	0.0136 (17)	−0.011 (2)
C6	0.051 (2)	0.086 (3)	0.055 (2)	−0.004 (2)	0.0036 (18)	−0.021 (2)
C7	0.050 (2)	0.077 (3)	0.060 (2)	−0.007 (2)	0.0014 (19)	−0.013 (2)
C8	0.043 (2)	0.071 (3)	0.057 (2)	−0.005 (2)	0.0104 (17)	−0.012 (2)
C9	0.047 (2)	0.061 (2)	0.062 (2)	−0.011 (2)	0.0115 (18)	−0.016 (2)
C10	0.048 (2)	0.065 (3)	0.055 (2)	−0.0087 (19)	0.0104 (18)	−0.0124 (19)
C11	0.0396 (18)	0.054 (2)	0.0447 (18)	0.0049 (17)	0.0134 (15)	0.0035 (17)
C12	0.051 (2)	0.073 (3)	0.045 (2)	0.003 (2)	0.0095 (17)	−0.0068 (18)
C13	0.057 (2)	0.080 (3)	0.057 (2)	0.008 (2)	0.0240 (19)	0.005 (2)
C14	0.059 (3)	0.076 (3)	0.075 (3)	−0.003 (2)	0.030 (2)	0.013 (2)
C15	0.061 (2)	0.055 (2)	0.063 (2)	−0.005 (2)	0.0163 (19)	0.0043 (19)
C16	0.0434 (19)	0.0472 (19)	0.0456 (18)	0.0069 (16)	0.0109 (15)	0.0045 (16)
C17	0.047 (2)	0.057 (2)	0.048 (2)	0.0009 (18)	0.0123 (16)	−0.0063 (18)
C18	0.055 (2)	0.074 (3)	0.046 (2)	−0.003 (2)	0.0127 (18)	−0.0011 (19)
C19	0.085 (3)	0.099 (3)	0.072 (3)	0.012 (3)	0.007 (2)	0.034 (3)
C20	0.054 (2)	0.057 (2)	0.048 (2)	−0.0041 (19)	0.0150 (17)	−0.0035 (18)
C21	0.074 (3)	0.105 (4)	0.112 (4)	0.034 (3)	0.017 (3)	−0.005 (3)
C22	0.106 (4)	0.093 (3)	0.074 (3)	0.039 (3)	0.015 (3)	0.021 (3)
C23	0.053 (2)	0.071 (3)	0.064 (3)	−0.006 (2)	0.011 (2)	−0.008 (2)
C24	0.085 (3)	0.078 (3)	0.103 (4)	0.004 (3)	0.013 (3)	0.006 (3)
C25	0.068 (3)	0.109 (4)	0.065 (3)	0.001 (3)	0.001 (2)	0.004 (3)

Geometric parameters (Å, º)

S—C2	1.758 (4)	C9—C10	1.442 (5)
S—C1	1.781 (5)	C10—C23	1.347 (5)
O1—C9	1.344 (4)	C11—C12	1.383 (5)
O1—N1	1.419 (4)	C11—C16	1.387 (5)
O2—C11	1.396 (4)	C12—C13	1.380 (5)
O2—C10	1.400 (4)	C12—H12A	0.9300
O3—C18	1.215 (4)	C13—C14	1.356 (5)
O4—C18	1.352 (4)	C13—H13A	0.9300
O4—C19	1.439 (4)	C14—C15	1.388 (5)
N1—C8	1.298 (5)	C14—H14A	0.9300
N2—C9	1.297 (5)	C15—C16	1.396 (5)
N2—C8	1.390 (5)	C15—H15A	0.9300
N3—C20	1.334 (4)	C16—C17	1.487 (4)
N3—C21	1.449 (5)	C17—C20	1.358 (5)
N3—C22	1.449 (5)	C17—C18	1.450 (5)
N4—C23	1.336 (5)	C19—H19A	0.9600
N4—C25	1.457 (5)	C19—H19B	0.9600
N4—C24	1.460 (5)	C19—H19C	0.9600
C1—H1B	0.9600	C20—H20A	0.9300
C1—H1C	0.9600	C21—H21A	0.9600
C1—H1D	0.9600	C21—H21B	0.9600
C2—C7	1.384 (5)	C21—H21C	0.9600
C2—C3	1.397 (5)	C22—H22A	0.9600
C3—C4	1.355 (5)	C22—H22B	0.9600
C3—H3A	0.9300	C22—H22C	0.9600
C4—C5	1.403 (5)	C23—H23A	0.9300
C4—H4A	0.9300	C24—H24A	0.9600
C5—C6	1.383 (5)	C24—H24B	0.9600
C5—C8	1.462 (5)	C24—H24C	0.9600
C6—C7	1.377 (5)	C25—H25A	0.9600
C6—H6A	0.9300	C25—H25B	0.9600
C7—H7A	0.9300	C25—H25C	0.9600
C2—S—C1	105.0 (2)	C12—C13—H13A	119.4
C9—O1—N1	106.4 (3)	C13—C14—C15	119.6 (4)
C11—O2—C10	118.1 (3)	C13—C14—H14A	120.2
C18—O4—C19	116.3 (3)	C15—C14—H14A	120.2
C8—N1—O1	103.1 (3)	C14—C15—C16	121.5 (4)
C9—N2—C8	102.4 (3)	C14—C15—H15A	119.2
C20—N3—C21	121.0 (3)	C16—C15—H15A	119.2
C20—N3—C22	124.3 (3)	C11—C16—C15	116.7 (3)
C21—N3—C22	114.7 (4)	C11—C16—C17	120.5 (3)
C23—N4—C25	124.5 (4)	C15—C16—C17	122.8 (3)
C23—N4—C24	119.8 (4)	C20—C17—C18	114.7 (3)
C25—N4—C24	115.6 (4)	C20—C17—C16	126.2 (3)
S—C1—H1B	109.5	C18—C17—C16	119.0 (3)
S—C1—H1C	109.5	O3—C18—O4	121.1 (4)
H1B—C1—H1C	109.5	O3—C18—C17	126.6 (4)
S—C1—H1D	109.5	O4—C18—C17	112.3 (3)
H1B—C1—H1D	109.5	O4—C19—H19A	109.5
H1C—C1—H1D	109.5	O4—C19—H19B	109.5
C7—C2—C3	117.3 (4)	H19A—C19—H19B	109.5
C7—C2—S	126.6 (3)	O4—C19—H19C	109.5
C3—C2—S	116.1 (3)	H19A—C19—H19C	109.5
C4—C3—C2	122.0 (4)	H19B—C19—H19C	109.5
C4—C3—H3A	119.0	N3—C20—C17	132.4 (3)
C2—C3—H3A	119.0	N3—C20—H20A	113.8
C3—C4—C5	120.7 (4)	C17—C20—H20A	113.8
C3—C4—H4A	119.7	N3—C21—H21A	109.5
C5—C4—H4A	119.7	N3—C21—H21B	109.5
C6—C5—C4	117.6 (4)	H21A—C21—H21B	109.5
C6—C5—C8	122.4 (3)	N3—C21—H21C	109.5
C4—C5—C8	120.0 (4)	H21A—C21—H21C	109.5
C7—C6—C5	121.4 (4)	H21B—C21—H21C	109.5
C7—C6—H6A	119.3	N3—C22—H22A	109.5
C5—C6—H6A	119.3	N3—C22—H22B	109.5
C6—C7—C2	121.1 (4)	H22A—C22—H22B	109.5
C6—C7—H7A	119.5	N3—C22—H22C	109.5
C2—C7—H7A	119.5	H22A—C22—H22C	109.5
N1—C8—N2	114.8 (4)	H22B—C22—H22C	109.5
N1—C8—C5	120.7 (4)	N4—C23—C10	132.3 (4)
N2—C8—C5	124.5 (3)	N4—C23—H23A	113.8
N2—C9—O1	113.3 (4)	C10—C23—H23A	113.8
N2—C9—C10	129.8 (3)	N4—C24—H24A	109.5
O1—C9—C10	117.0 (4)	N4—C24—H24B	109.5
C23—C10—O2	123.4 (4)	H24A—C24—H24B	109.5
C23—C10—C9	121.6 (3)	N4—C24—H24C	109.5
O2—C10—C9	114.8 (3)	H24A—C24—H24C	109.5
C12—C11—C16	122.5 (3)	H24B—C24—H24C	109.5
C12—C11—O2	122.8 (3)	N4—C25—H25A	109.5
C16—C11—O2	114.8 (3)	N4—C25—H25B	109.5
C13—C12—C11	118.5 (3)	H25A—C25—H25B	109.5
C13—C12—H12A	120.7	N4—C25—H25C	109.5
C11—C12—H12A	120.7	H25A—C25—H25C	109.5
C14—C13—C12	121.2 (4)	H25B—C25—H25C	109.5
C14—C13—H13A	119.4
C9—O1—N1—C8	0.6 (4)	C10—O2—C11—C12	−3.3 (5)
C1—S—C2—C7	7.0 (4)	C10—O2—C11—C16	176.6 (3)
C1—S—C2—C3	−174.5 (3)	C16—C11—C12—C13	0.0 (5)
C7—C2—C3—C4	0.7 (6)	O2—C11—C12—C13	180.0 (3)
S—C2—C3—C4	−177.9 (3)	C11—C12—C13—C14	−0.4 (6)
C2—C3—C4—C5	−0.1 (6)	C12—C13—C14—C15	0.9 (6)
C3—C4—C5—C6	−0.6 (5)	C13—C14—C15—C16	−1.1 (6)
C3—C4—C5—C8	178.3 (3)	C12—C11—C16—C15	−0.2 (5)
C4—C5—C6—C7	0.7 (5)	O2—C11—C16—C15	179.8 (3)
C8—C5—C6—C7	−178.2 (3)	C12—C11—C16—C17	−179.0 (3)
C5—C6—C7—C2	−0.1 (6)	O2—C11—C16—C17	1.0 (4)
C3—C2—C7—C6	−0.6 (6)	C14—C15—C16—C11	0.7 (5)
S—C2—C7—C6	177.9 (3)	C14—C15—C16—C17	179.5 (3)
O1—N1—C8—N2	−1.4 (4)	C11—C16—C17—C20	−89.7 (4)
O1—N1—C8—C5	−179.1 (3)	C15—C16—C17—C20	91.6 (5)
C9—N2—C8—N1	1.7 (4)	C11—C16—C17—C18	86.8 (4)
C9—N2—C8—C5	179.3 (3)	C15—C16—C17—C18	−91.9 (4)
C6—C5—C8—N1	167.3 (4)	C19—O4—C18—O3	0.2 (6)
C4—C5—C8—N1	−11.6 (5)	C19—O4—C18—C17	−179.6 (3)
C6—C5—C8—N2	−10.2 (6)	C20—C17—C18—O3	6.4 (6)
C4—C5—C8—N2	171.0 (3)	C16—C17—C18—O3	−170.4 (4)
C8—N2—C9—O1	−1.2 (4)	C20—C17—C18—O4	−173.8 (3)
C8—N2—C9—C10	178.8 (4)	C16—C17—C18—O4	9.4 (5)
N1—O1—C9—N2	0.4 (4)	C21—N3—C20—C17	−178.1 (4)
N1—O1—C9—C10	−179.6 (3)	C22—N3—C20—C17	−0.1 (7)
C11—O2—C10—C23	103.1 (4)	C18—C17—C20—N3	−177.3 (4)
C11—O2—C10—C9	−81.8 (4)	C16—C17—C20—N3	−0.8 (6)
N2—C9—C10—C23	178.3 (4)	C25—N4—C23—C10	0.7 (7)
O1—C9—C10—C23	−1.6 (6)	C24—N4—C23—C10	177.0 (4)
N2—C9—C10—O2	3.1 (6)	O2—C10—C23—N4	−4.9 (7)
O1—C9—C10—O2	−176.8 (3)	C9—C10—C23—N4	−179.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O3	0.93	2.34	2.756 (5)	107
C23—H23A···O1	0.93	2.34	2.757 (3)	107
C25—H25A···O2	0.96	2.20	2.959 (5)	135
C25—H25B···Cg2^i	0.96	2.88	3.783 (1)	158

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.