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

The title compound, C₂₄H₂₅ClN₄O₄, was obtained from the reaction of methyl 2-{[3-(2-bromo­phen­yl)-1,2,4-oxadiazol-5-yl]meth­oxy}phenyl­acetate with N,N-dimethyl­formamide dimethyl acetal. The mol­ecules inter­act through weak C—H...O inter­molecular hydrogen bonds to form a zigzag chain parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.069
• wR factor = 0.172
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   0 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
   0 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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

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

Crystal data

C24H25BrN4O4	F(000) = 1056
Mr = 513.39	Dx = 1.450 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 15.479 (3) Å	θ = 9–12°
b = 8.5690 (17) Å	µ = 1.79 mm^−1
c = 17.919 (4) Å	T = 293 K
β = 98.37 (3)°	Block, colourless
V = 2351.5 (9) Å^3	0.40 × 0.30 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1956 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 26.0°, θmin = 1.6°
ω/2θ scans	h = 0→19
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.535, Tmax = 0.842	l = −22→21
4779 measured reflections	3 standard reflections every 200 reflections
4603 independent reflections	intensity decay: none

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0685P)^2] where P = (Fo^2 + 2Fc^2)/3
4603 reflections	(Δ/σ)max = 0.032
303 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 7.77–7.79 (m, 1H), 7.68 (s, 1H), 7.46–7.48 (m, 1H), 7.34–38 (m, 1H), 7.29–7.32 (m, 2H), 7.17–7.20 (m, 2H), 6.93–6.97 (m, 1H), 6.89–6.91 (m, 1H), 3.55 (s, 3H), 3.01 (s, 6H), 2.82 (s, 6H).

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
Br	0.94458 (5)	0.76743 (8)	0.56809 (5)	0.0919 (4)
O1	0.7163 (3)	−0.0515 (5)	0.6679 (2)	0.0713 (13)
O2	0.6984 (2)	−0.2752 (4)	0.49564 (19)	0.0445 (9)
O3	0.7908 (3)	−0.6172 (4)	0.3535 (2)	0.0605 (11)
O4	0.6514 (3)	−0.5581 (4)	0.3607 (2)	0.0614 (11)
N1	0.7546 (4)	0.0985 (6)	0.6809 (3)	0.0708 (15)
N2	0.7538 (3)	0.0257 (5)	0.5593 (2)	0.0459 (12)
C1	0.5801 (4)	−0.5530 (8)	0.6657 (3)	0.076 (2)
H1A	0.5924	−0.4911	0.7106	0.114*
H1B	0.6086	−0.6524	0.6737	0.114*
H1C	0.5182	−0.5685	0.6537	0.114*
C2	0.6107 (4)	−0.5610 (7)	0.5344 (3)	0.0651 (17)
H2A	0.5920	−0.4947	0.4919	0.098*
H2B	0.5710	−0.6471	0.5342	0.098*
H2C	0.6682	−0.5998	0.5312	0.098*
N3	0.6120 (3)	−0.4729 (6)	0.6034 (3)	0.0573 (13)
C3	0.6470 (3)	−0.3298 (7)	0.6138 (3)	0.0500 (15)
H3	0.6459	−0.2899	0.6620	0.060*
C4	0.6834 (3)	−0.2326 (6)	0.5680 (3)	0.0429 (13)
C5	0.7189 (3)	−0.0862 (7)	0.5941 (3)	0.0441 (14)
C6	0.7753 (3)	0.1360 (6)	0.6151 (3)	0.0450 (14)
C7	0.8165 (3)	0.2853 (6)	0.6030 (3)	0.0444 (14)
C8	0.8237 (4)	0.3995 (7)	0.6592 (3)	0.0553 (16)
H8	0.8028	0.3790	0.7043	0.066*
C9	0.8613 (4)	0.5417 (7)	0.6488 (4)	0.0583 (17)
H9	0.8647	0.6179	0.6860	0.070*
C10	0.8936 (4)	0.5697 (7)	0.5825 (4)	0.0567 (16)
C11	0.8863 (3)	0.4619 (7)	0.5250 (3)	0.0556 (16)
H11	0.9061	0.4844	0.4796	0.067*
C12	0.8486 (3)	0.3183 (7)	0.5367 (3)	0.0484 (15)
H12	0.8449	0.2428	0.4991	0.058*
C13	0.6453 (3)	−0.2127 (5)	0.4338 (3)	0.0372 (12)
C14	0.5728 (3)	−0.1235 (6)	0.4398 (3)	0.0453 (14)
H14	0.5572	−0.1035	0.4870	0.054*
C15	0.5233 (3)	−0.0637 (6)	0.3764 (3)	0.0522 (15)
H15	0.4745	−0.0027	0.3805	0.063*
C16	0.5465 (3)	−0.0951 (6)	0.3068 (3)	0.0505 (15)
H16	0.5134	−0.0547	0.2636	0.061*
C17	0.6187 (4)	−0.1865 (6)	0.3006 (3)	0.0516 (15)
H17	0.6332	−0.2078	0.2531	0.062*
C18	0.6701 (3)	−0.2471 (5)	0.3641 (3)	0.0357 (12)
C19	0.9558 (4)	−0.1468 (8)	0.3386 (4)	0.087 (2)
H19A	0.9888	−0.1101	0.3848	0.131*
H19B	0.9614	−0.0740	0.2989	0.131*
H19C	0.9776	−0.2468	0.3260	0.131*
C20	0.8205 (4)	−0.0161 (6)	0.3626 (3)	0.0657 (18)
H20A	0.7775	0.0086	0.3200	0.099*
H20B	0.8624	0.0669	0.3709	0.099*
H20C	0.7924	−0.0288	0.4066	0.099*
N4	0.8648 (3)	−0.1609 (5)	0.3478 (3)	0.0542 (13)
C21	0.8283 (4)	−0.3039 (6)	0.3484 (3)	0.0469 (15)
H21	0.8658	−0.3860	0.3418	0.056*
C22	0.7464 (3)	−0.3477 (6)	0.3571 (3)	0.0390 (13)
C23	0.7346 (4)	−0.5182 (7)	0.3566 (3)	0.0487 (15)
C24	0.6341 (5)	−0.7234 (6)	0.3621 (4)	0.082 (2)
H24A	0.6497	−0.7712	0.3175	0.123*
H24B	0.5731	−0.7401	0.3640	0.123*
H24C	0.6680	−0.7689	0.4059	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0854 (5)	0.0546 (5)	0.1364 (8)	−0.0135 (4)	0.0183 (5)	−0.0120 (5)
O1	0.123 (4)	0.055 (3)	0.039 (2)	−0.020 (3)	0.022 (2)	−0.002 (2)
O2	0.049 (2)	0.045 (2)	0.040 (2)	0.0147 (18)	0.0070 (18)	−0.0022 (19)
O3	0.081 (3)	0.043 (2)	0.061 (3)	0.010 (2)	0.024 (2)	−0.006 (2)
O4	0.071 (3)	0.031 (2)	0.085 (3)	−0.007 (2)	0.021 (2)	−0.002 (2)
N1	0.115 (4)	0.062 (4)	0.039 (3)	−0.021 (3)	0.023 (3)	−0.009 (3)
N2	0.056 (3)	0.043 (3)	0.039 (3)	0.003 (2)	0.008 (2)	−0.002 (2)
C1	0.091 (5)	0.071 (5)	0.069 (4)	−0.016 (4)	0.019 (4)	0.013 (4)
C2	0.068 (4)	0.055 (4)	0.071 (4)	0.006 (3)	0.007 (4)	−0.004 (4)
N3	0.064 (3)	0.055 (3)	0.054 (3)	−0.012 (3)	0.012 (3)	0.001 (3)
C3	0.055 (4)	0.055 (4)	0.041 (3)	0.005 (3)	0.009 (3)	0.005 (3)
C4	0.048 (3)	0.049 (4)	0.034 (3)	0.009 (3)	0.013 (3)	−0.002 (3)
C5	0.053 (4)	0.049 (4)	0.032 (3)	0.007 (3)	0.011 (3)	0.001 (3)
C6	0.049 (3)	0.046 (4)	0.040 (3)	0.003 (3)	0.008 (3)	0.000 (3)
C7	0.047 (3)	0.047 (3)	0.037 (3)	0.010 (3)	−0.001 (3)	−0.003 (3)
C8	0.064 (4)	0.058 (4)	0.041 (3)	0.005 (3)	0.000 (3)	−0.008 (3)
C9	0.062 (4)	0.051 (4)	0.059 (4)	0.006 (3)	−0.004 (3)	−0.021 (3)
C10	0.053 (4)	0.044 (4)	0.070 (4)	−0.005 (3)	−0.003 (3)	−0.002 (4)
C11	0.052 (4)	0.057 (4)	0.057 (4)	−0.004 (3)	0.004 (3)	0.000 (3)
C12	0.052 (4)	0.048 (4)	0.045 (4)	−0.003 (3)	0.006 (3)	−0.010 (3)
C13	0.039 (3)	0.029 (3)	0.045 (3)	−0.002 (2)	0.008 (3)	0.004 (3)
C14	0.049 (3)	0.039 (3)	0.048 (4)	0.007 (3)	0.007 (3)	−0.004 (3)
C15	0.044 (3)	0.038 (3)	0.073 (4)	0.005 (3)	0.004 (3)	0.000 (3)
C16	0.052 (4)	0.044 (3)	0.051 (4)	0.004 (3)	−0.008 (3)	0.013 (3)
C17	0.068 (4)	0.048 (4)	0.039 (3)	−0.004 (3)	0.010 (3)	0.000 (3)
C18	0.041 (3)	0.027 (3)	0.039 (3)	−0.005 (2)	0.007 (3)	0.002 (3)
C19	0.058 (4)	0.077 (5)	0.132 (7)	−0.010 (4)	0.031 (4)	−0.009 (5)
C20	0.074 (4)	0.040 (4)	0.085 (5)	−0.014 (3)	0.020 (4)	−0.012 (3)
N4	0.048 (3)	0.049 (3)	0.069 (3)	−0.002 (3)	0.018 (2)	−0.003 (3)
C21	0.056 (4)	0.034 (3)	0.053 (4)	0.008 (3)	0.016 (3)	−0.005 (3)
C22	0.050 (3)	0.036 (3)	0.034 (3)	0.002 (3)	0.013 (3)	0.000 (3)
C23	0.058 (4)	0.042 (4)	0.049 (4)	0.007 (3)	0.018 (3)	−0.007 (3)
C24	0.102 (5)	0.032 (4)	0.115 (6)	−0.019 (3)	0.029 (5)	−0.008 (4)

Geometric parameters (Å, º)

Br—C10	1.902 (6)	C10—C11	1.377 (8)
O1—C5	1.361 (6)	C11—C12	1.391 (7)
O1—N1	1.420 (6)	C11—H11	0.9300
O2—C13	1.387 (6)	C12—H12	0.9300
O2—C4	1.398 (6)	C13—C14	1.375 (6)
O3—C23	1.222 (6)	C13—C18	1.390 (7)
O4—C23	1.345 (6)	C14—C15	1.374 (7)
O4—C24	1.442 (6)	C14—H14	0.9300
N1—C6	1.306 (7)	C15—C16	1.374 (7)
N2—C5	1.304 (6)	C15—H15	0.9300
N2—C6	1.381 (6)	C16—C17	1.383 (7)
C1—N3	1.456 (7)	C16—H16	0.9300
C1—H1A	0.9600	C17—C18	1.390 (7)
C1—H1B	0.9600	C17—H17	0.9300
C1—H1C	0.9600	C18—C22	1.483 (7)
C2—N3	1.447 (7)	C19—N4	1.448 (7)
C2—H2A	0.9600	C19—H19A	0.9600
C2—H2B	0.9600	C19—H19B	0.9600
C2—H2C	0.9600	C19—H19C	0.9600
N3—C3	1.343 (7)	C20—N4	1.460 (7)
C3—C4	1.349 (7)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.421 (7)	C20—H20C	0.9600
C6—C7	1.459 (7)	N4—C21	1.349 (7)
C7—C12	1.382 (7)	C21—C22	1.353 (7)
C7—C8	1.397 (7)	C21—H21	0.9300
C8—C9	1.374 (8)	C22—C23	1.472 (7)
C8—H8	0.9300	C24—H24A	0.9600
C9—C10	1.375 (8)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C5—O1—N1	106.7 (4)	C11—C12—H12	119.3
C13—O2—C4	118.7 (4)	C14—C13—O2	123.3 (5)
C23—O4—C24	115.6 (5)	C14—C13—C18	121.5 (5)
C6—N1—O1	103.0 (4)	O2—C13—C18	115.3 (4)
C5—N2—C6	103.3 (4)	C15—C14—C13	120.5 (5)
N3—C1—H1A	109.5	C15—C14—H14	119.8
N3—C1—H1B	109.5	C13—C14—H14	119.8
H1A—C1—H1B	109.5	C16—C15—C14	119.3 (5)
N3—C1—H1C	109.5	C16—C15—H15	120.3
H1A—C1—H1C	109.5	C14—C15—H15	120.3
H1B—C1—H1C	109.5	C15—C16—C17	120.3 (5)
N3—C2—H2A	109.5	C15—C16—H16	119.9
N3—C2—H2B	109.5	C17—C16—H16	119.9
H2A—C2—H2B	109.5	C16—C17—C18	121.3 (5)
N3—C2—H2C	109.5	C16—C17—H17	119.4
H2A—C2—H2C	109.5	C18—C17—H17	119.4
H2B—C2—H2C	109.5	C17—C18—C13	117.2 (5)
C3—N3—C2	123.4 (5)	C17—C18—C22	121.0 (5)
C3—N3—C1	120.0 (5)	C13—C18—C22	121.8 (4)
C2—N3—C1	116.4 (5)	N4—C19—H19A	109.5
N3—C3—C4	132.4 (6)	N4—C19—H19B	109.5
N3—C3—H3	113.8	H19A—C19—H19B	109.5
C4—C3—H3	113.8	N4—C19—H19C	109.5
C3—C4—O2	123.0 (5)	H19A—C19—H19C	109.5
C3—C4—C5	121.3 (5)	H19B—C19—H19C	109.5
O2—C4—C5	115.3 (5)	N4—C20—H20A	109.5
N2—C5—O1	112.1 (5)	N4—C20—H20B	109.5
N2—C5—C4	131.2 (5)	H20A—C20—H20B	109.5
O1—C5—C4	116.7 (5)	N4—C20—H20C	109.5
N1—C6—N2	114.8 (5)	H20A—C20—H20C	109.5
N1—C6—C7	121.3 (5)	H20B—C20—H20C	109.5
N2—C6—C7	123.9 (5)	C21—N4—C19	119.5 (5)
C12—C7—C8	118.4 (5)	C21—N4—C20	124.2 (4)
C12—C7—C6	121.8 (5)	C19—N4—C20	116.1 (5)
C8—C7—C6	119.8 (5)	N4—C21—C22	130.7 (5)
C9—C8—C7	120.9 (6)	N4—C21—H21	114.6
C9—C8—H8	119.6	C22—C21—H21	114.6
C7—C8—H8	119.6	C21—C22—C23	113.1 (5)
C8—C9—C10	119.2 (6)	C21—C22—C18	128.3 (5)
C8—C9—H9	120.4	C23—C22—C18	118.5 (5)
C10—C9—H9	120.4	O3—C23—O4	121.3 (5)
C9—C10—C11	121.9 (6)	O3—C23—C22	127.0 (6)
C9—C10—Br	118.9 (5)	O4—C23—C22	111.8 (5)
C11—C10—Br	119.1 (5)	O4—C24—H24A	109.5
C10—C11—C12	118.1 (6)	O4—C24—H24B	109.5
C10—C11—H11	120.9	H24A—C24—H24B	109.5
C12—C11—H11	120.9	O4—C24—H24C	109.5
C7—C12—C11	121.5 (5)	H24A—C24—H24C	109.5
C7—C12—H12	119.3	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.43	3.274 (7)	152
C17—H17···O3^ii	0.93	2.51	3.327 (7)	147

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