(2E)-Methyl 2-{2-[6-(2-cyano­phen­oxy)pyrimidin-4-yl­oxy]phen­yl}-3-methoxy­acrylate

Chopra, D.; Mohan, T.P.; Rao, K.S.; Guru Row, T.N.

doi:10.1107/S1600536807052956

(2E)-Methyl 2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate

D. Chopra, T. P. Mohan, K. S. Rao and T. N. Guru Row

The title compound, C₂₂H₁₆N₃O₅, also known as azoxystrobin, possesses fungicidal properties. The dihedral angles between the cyanophenoxy and oxophenyl rings and the central pyrimidinyl ring are 80.5 (2) and 76.0 (1)°, respectively. The crystal structure is stabilized by aromatic π–π staching interactions between the pyrimide rings, the centroid–centroid distance being 3.914 (9) Å.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052956/sj2388sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052956/sj2388Isup2.hkl Contains datablock I

CCDC reference: 667485

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.079
wR factor = 0.220
Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4999

Author Response: Repeated attempts to grow a better quality crystal with improved morphology failed and hence the extent of diffraction observed is poor.

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      20.81 Deg.

Author Response: Repeated attempts to grow a better quality crystal with improved morphology failed and hence the extent of diffraction observed is poor.

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      20.81 Deg.

Author Response: Repeated attempts to grow a better quality crystal with improved morphology failed and hence the extent of diffraction observed is poor.

PLAT430_ALERT_2_A Short Inter D...A Contact  O4     ..  O4      ..       2.43 Ang.

Author Response: This short contact is generated as a consequence of disorder of the oxygen atom into two sites O4 and O4A in the ratio of 1:1. In fact, from CD studies such contacts have been proven to have bonding nature and are closed-shell interactions (Chen et al., Acta Cryst., 2007, B63, 309).

PLAT430_ALERT_2_A Short Inter D...A Contact  O4A    ..  O4A     ..       2.39 Ang.


Alert level B
REFNR01_ALERT_3_B  Ratio of reflections to parameters is < 8 for a
            centrosymmetric structure
            sine(theta)/lambda                0.4999
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.6643
PLAT088_ALERT_3_B Poor Data / Parameter Ratio ....................       7.66

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O3
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O4A
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.39 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C7     ...       1.45 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

An important aspect in the rational design of bioactive molecules involves relating chemical structure to biological activity (Lewis et al., 1991). The conformation of the molecule is found to influence the levels of biological activity. Correlation of the results obtained from X-ray crystallography with biological activity has aided in the chemical design of few active agrochemicals. The activity of a series of triazolyl ketone herbicides (Anderson et al., 1983) has been investigated along with the fungicidal activities of N-phenyl succinamides (Zenei et al., 1988).

The title compound, (I), has been shown to have fungicidal properties and its structure is reported here, Fig. 1. Bond lengths and angles observed in the structure are normal (Allen et al., 1987). The crystal structure is stabilized by aromatic stacking π···π interactions (Fig. 2) between the pyrimidyl rings, the centroid to centroid distance being 3.914 (9) Å (Symmetry Code: -x + 1/2, -y + 3 /2, -z + 1).

Related literature top

For related structures, see: Lewis et al. (1991); Anderson et al. (1983); Zenei et al. (1988).

For related literature, see: Allen et al. (1987).

Experimental top

The title compound was obtained from Rallis India, Bangalore. Single crystals of the compound were grown by the slow evaporation method from acetone at 278 K.

Structure description top

For related structures, see: Lewis et al. (1991); Anderson et al. (1983); Zenei et al. (1988).

For related literature, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), showing 50% ellipsoidal probability.
	Fig. 2. Part of the packing diagram for (I), highlighting the π···π intermolecular interactions (dotted line).

(2E)-Methyl 2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate top

Crystal data top

C₂₂H₁₆N₃O₅	F(000) = 1672
M_r = 402.38	D_x = 1.289 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 565 reflections
a = 28.946 (6) Å	θ = 1.2–19.6°
b = 10.803 (2) Å	µ = 0.09 mm⁻¹
c = 13.302 (3) Å	T = 292 K
β = 94.61 (3)°	Plate, colorless
V = 4146.1 (15) Å³	0.08 × 0.07 × 0.02 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1733 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 20.8°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a)	h = −28→28
T_min = 0.948, T_max = 0.998	k = −10→10
9000 measured reflections	l = −13→13

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.1574P)² + 9.0867P] where P = (F_o² + 2F_c²)/3
2169 reflections	(Δ/σ)_max < 0.001
283 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₂H₁₆N₃O₅	V = 4146.1 (15) Å³
M_r = 402.38	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.946 (6) Å	µ = 0.09 mm⁻¹
b = 10.803 (2) Å	T = 292 K
c = 13.302 (3) Å	0.08 × 0.07 × 0.02 mm
β = 94.61 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2169 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a)	1733 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.998	R_int = 0.055
9000 measured reflections	θ_max = 20.8°

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.14	Δρ_max = 0.31 e Å⁻³
2169 reflections	Δρ_min = −0.39 e Å⁻³
283 parameters

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	U_iso*/U_eq	Occ. (<1)
O1	0.72469 (11)	0.4309 (3)	0.3502 (2)	0.0658 (10)
O2	0.62147 (10)	0.1461 (3)	0.4936 (2)	0.0648 (9)
O3	0.51541 (13)	0.2021 (4)	0.4877 (3)	0.0971 (13)
O4	0.5153 (3)	0.4039 (9)	0.4684 (6)	0.103 (4)	0.517 (11)
O4A	0.5367 (3)	0.4936 (7)	0.2981 (7)	0.106 (4)	0.483 (11)
O5	0.58850 (14)	0.3775 (3)	0.2208 (3)	0.0872 (12)
N1	0.63577 (19)	0.6404 (5)	0.4033 (4)	0.1047 (17)
N2	0.72237 (14)	0.4148 (3)	0.5245 (3)	0.0660 (12)
N3	0.67012 (15)	0.2677 (4)	0.5918 (3)	0.0707 (12)
C1	0.7935 (2)	0.7708 (5)	0.3623 (4)	0.0715 (15)
C2	0.81804 (17)	0.6609 (5)	0.3512 (4)	0.0713 (14)
C3	0.79544 (16)	0.5464 (4)	0.3512 (3)	0.0631 (13)
C4	0.74871 (16)	0.5440 (4)	0.3622 (3)	0.0530 (12)
C5	0.72374 (15)	0.6540 (4)	0.3753 (3)	0.0575 (13)
C6	0.74707 (18)	0.7679 (5)	0.3748 (3)	0.0650 (13)
C7	0.6746 (2)	0.6477 (5)	0.3900 (4)	0.0736 (15)
C8	0.70679 (15)	0.3777 (4)	0.4317 (3)	0.0519 (12)
C9	0.7029 (2)	0.3558 (5)	0.5980 (4)	0.0783 (16)
C10	0.65564 (15)	0.2350 (4)	0.4959 (3)	0.0517 (12)
C11	0.67341 (14)	0.2847 (4)	0.4135 (3)	0.0527 (12)
C12	0.60626 (15)	0.0952 (4)	0.3966 (3)	0.0565 (12)
C13	0.62339 (17)	−0.0210 (5)	0.3743 (4)	0.0727 (14)
C14	0.60929 (19)	−0.0757 (5)	0.2829 (4)	0.0801 (16)
C15	0.57760 (18)	−0.0146 (5)	0.2143 (4)	0.0806 (16)
C16	0.56032 (16)	0.1001 (5)	0.2397 (4)	0.0687 (14)
C17	0.57395 (14)	0.1586 (4)	0.3327 (3)	0.0561 (12)
C18	0.55490 (15)	0.2839 (4)	0.3569 (4)	0.0621 (14)
C19	0.52730 (19)	0.3029 (6)	0.4364 (5)	0.0782 (16)
C20	0.4827 (3)	0.2207 (9)	0.5632 (7)	0.155 (3)
C21	0.5617 (2)	0.3891 (6)	0.2961 (5)	0.0779 (16)
C22	0.5905 (2)	0.4881 (7)	0.1568 (6)	0.123 (3)
H1	0.8088	0.8464	0.3611	0.086*
H2	0.8497	0.6639	0.3438	0.086*
H3	0.8118	0.4733	0.3439	0.076*
H6	0.7310	0.8413	0.3829	0.078*
H9	0.7136	0.3790	0.6631	0.094*
H11	0.6639	0.2584	0.3485	0.063*
H13	0.6441	−0.0614	0.4203	0.087*
H14	0.6208	−0.1530	0.2669	0.096*
H15	0.5683	−0.0506	0.1525	0.097*
H16	0.5392	0.1398	0.1943	0.082*
H20A	0.4989	0.2502	0.6244	0.233*
H20B	0.4677	0.1438	0.5760	0.233*
H20C	0.4599	0.2806	0.5392	0.233*
H22A	0.5659	0.5436	0.1705	0.185*
H22B	0.5872	0.4640	0.0871	0.185*
H22C	0.6198	0.5288	0.1711	0.185*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.076 (2)	0.063 (2)	0.056 (2)	−0.0193 (17)	−0.0109 (16)	−0.0068 (16)
O2	0.063 (2)	0.065 (2)	0.063 (2)	−0.0096 (17)	−0.0157 (16)	0.0085 (16)
O3	0.069 (2)	0.116 (3)	0.107 (3)	0.010 (2)	0.009 (2)	0.009 (3)
O4	0.092 (6)	0.115 (7)	0.102 (6)	0.036 (5)	0.000 (4)	−0.027 (5)
O4A	0.120 (7)	0.058 (6)	0.134 (8)	0.004 (5)	−0.021 (5)	−0.006 (5)
O5	0.089 (3)	0.068 (3)	0.100 (3)	0.003 (2)	−0.016 (2)	0.023 (2)
N1	0.068 (3)	0.112 (4)	0.132 (5)	0.013 (3)	−0.004 (3)	0.011 (3)
N2	0.087 (3)	0.053 (2)	0.053 (3)	−0.008 (2)	−0.028 (2)	0.000 (2)
N3	0.097 (3)	0.058 (3)	0.053 (3)	−0.007 (2)	−0.017 (2)	0.007 (2)
C1	0.085 (4)	0.061 (3)	0.067 (3)	−0.018 (3)	−0.010 (3)	0.005 (2)
C2	0.054 (3)	0.078 (4)	0.079 (3)	−0.010 (3)	−0.013 (2)	0.009 (3)
C3	0.056 (3)	0.061 (3)	0.070 (3)	0.001 (3)	−0.011 (2)	0.008 (2)
C4	0.057 (3)	0.052 (3)	0.046 (3)	−0.010 (2)	−0.019 (2)	0.001 (2)
C5	0.054 (3)	0.064 (3)	0.051 (3)	−0.002 (3)	−0.017 (2)	0.002 (2)
C6	0.072 (4)	0.059 (3)	0.062 (3)	0.004 (3)	−0.011 (2)	0.002 (2)
C7	0.072 (4)	0.071 (4)	0.075 (3)	0.009 (3)	−0.014 (3)	0.003 (3)
C8	0.056 (3)	0.046 (3)	0.050 (3)	0.008 (2)	−0.015 (2)	0.000 (2)
C9	0.118 (4)	0.061 (3)	0.050 (3)	−0.018 (3)	−0.027 (3)	0.006 (3)
C10	0.055 (3)	0.041 (3)	0.056 (3)	0.005 (2)	−0.018 (2)	0.005 (2)
C11	0.051 (3)	0.051 (3)	0.053 (3)	−0.005 (2)	−0.019 (2)	−0.005 (2)
C12	0.052 (3)	0.051 (3)	0.064 (3)	−0.004 (2)	−0.009 (2)	0.001 (2)
C13	0.069 (3)	0.065 (4)	0.082 (4)	0.002 (3)	−0.012 (3)	0.002 (3)
C14	0.079 (4)	0.058 (3)	0.101 (4)	0.004 (3)	−0.008 (3)	−0.004 (3)
C15	0.074 (4)	0.073 (4)	0.093 (4)	−0.020 (3)	−0.003 (3)	−0.019 (3)
C16	0.045 (3)	0.072 (4)	0.086 (4)	−0.004 (2)	−0.018 (2)	−0.007 (3)
C17	0.043 (3)	0.056 (3)	0.066 (3)	−0.006 (2)	−0.014 (2)	−0.001 (2)
C18	0.046 (3)	0.068 (4)	0.068 (3)	0.000 (2)	−0.020 (3)	−0.009 (3)
C19	0.057 (3)	0.085 (4)	0.089 (4)	0.005 (3)	−0.020 (3)	−0.008 (4)
C20	0.114 (6)	0.220 (10)	0.137 (7)	0.023 (6)	0.040 (6)	0.028 (6)
C21	0.067 (4)	0.079 (4)	0.084 (4)	−0.010 (3)	−0.024 (3)	−0.002 (3)
C22	0.116 (5)	0.111 (5)	0.137 (6)	−0.019 (4)	−0.030 (4)	0.033 (5)

Geometric parameters (Å, º) top

O4—C19	1.230 (9)	C18—C21	1.418 (8)
O4A—C21	1.342 (10)	C4—C3	1.372 (7)
O1—C8	1.366 (5)	C2—C1	1.398 (7)
O1—C4	1.409 (6)	C2—C3	1.399 (7)
O2—C10	1.377 (5)	C2—H2	0.9300
O2—C12	1.439 (6)	N1—C7	1.154 (7)
N2—C9	1.329 (6)	C3—H3	0.9300
N2—C8	1.342 (6)	C13—C14	1.384 (7)
O5—C21	1.321 (7)	C13—H13	0.9300
O5—C22	1.471 (8)	C6—C1	1.367 (7)
O3—C19	1.345 (7)	C6—H6	0.9300
O3—C20	1.448 (8)	C14—C15	1.406 (8)
C10—N3	1.357 (6)	C14—H14	0.9300
C10—C11	1.358 (6)	C15—C16	1.388 (7)
N3—C9	1.342 (7)	C15—H15	0.9300
C17—C12	1.392 (6)	C9—H9	0.9300
C17—C16	1.417 (7)	C16—H16	0.9300
C17—C18	1.506 (7)	C1—H1	0.9300
C8—C11	1.401 (6)	C22—H22A	0.9600
C11—H11	0.9300	C22—H22B	0.9600
C12—C13	1.390 (7)	C22—H22C	0.9600
C5—C6	1.404 (7)	C20—H20A	0.9600
C5—C4	1.409 (7)	C20—H20B	0.9600
C5—C7	1.453 (8)	C20—H20C	0.9600
C18—C19	1.391 (8)

C8—O1—C4	119.4 (3)	C12—C13—H13	120.4
C10—O2—C12	116.9 (3)	N1—C7—C5	178.3 (6)
C9—N2—C8	113.8 (4)	C1—C6—C5	119.9 (5)
C21—O5—C22	114.5 (5)	C1—C6—H6	120.0
C19—O3—C20	116.6 (6)	C5—C6—H6	120.0
N3—C10—C11	123.2 (4)	O5—C21—O4A	116.5 (6)
N3—C10—O2	111.7 (4)	O5—C21—C18	118.2 (5)
C11—C10—O2	125.2 (4)	O4A—C21—C18	124.3 (7)
C9—N3—C10	114.0 (4)	C13—C14—C15	120.0 (5)
C12—C17—C16	116.1 (4)	C13—C14—H14	120.0
C12—C17—C18	123.4 (4)	C15—C14—H14	120.0
C16—C17—C18	120.4 (4)	O4—C19—O3	116.9 (7)
N2—C8—O1	119.0 (4)	O4—C19—C18	126.0 (7)
N2—C8—C11	123.3 (4)	O3—C19—C18	116.8 (6)
O1—C8—C11	117.7 (4)	C16—C15—C14	119.4 (5)
C10—C11—C8	116.4 (4)	C16—C15—H15	120.3
C10—C11—H11	121.8	C14—C15—H15	120.3
C8—C11—H11	121.8	N2—C9—N3	129.4 (4)
C13—C12—C17	123.2 (4)	N2—C9—H9	115.3
C13—C12—O2	116.6 (4)	N3—C9—H9	115.3
C17—C12—O2	120.1 (4)	C15—C16—C17	122.0 (5)
C6—C5—C4	119.1 (4)	C15—C16—H16	119.0
C6—C5—C7	121.2 (4)	C17—C16—H16	119.0
C4—C5—C7	119.6 (4)	C6—C1—C2	120.4 (5)
C19—C18—C21	115.4 (5)	C6—C1—H1	119.8
C19—C18—C17	122.5 (5)	C2—C1—H1	119.8
C21—C18—C17	121.9 (5)	O5—C22—H22A	109.5
C3—C4—O1	119.1 (4)	O5—C22—H22B	109.5
C3—C4—C5	121.1 (4)	H22A—C22—H22B	109.5
O1—C4—C5	119.5 (4)	O5—C22—H22C	109.5
C1—C2—C3	120.6 (5)	H22A—C22—H22C	109.5
C1—C2—H2	119.7	H22B—C22—H22C	109.5
C3—C2—H2	119.7	O3—C20—H20A	109.5
C4—C3—C2	118.8 (4)	O3—C20—H20B	109.5
C4—C3—H3	120.6	H20A—C20—H20B	109.5
C2—C3—H3	120.6	O3—C20—H20C	109.5
C14—C13—C12	119.2 (5)	H20A—C20—H20C	109.5
C14—C13—H13	120.4	H20B—C20—H20C	109.5

C12—O2—C10—N3	−174.3 (3)	O1—C4—C3—C2	172.4 (4)
C12—O2—C10—C11	5.3 (6)	C5—C4—C3—C2	−1.2 (6)
C11—C10—N3—C9	1.4 (7)	C1—C2—C3—C4	0.0 (7)
O2—C10—N3—C9	−178.9 (4)	C17—C12—C13—C14	2.4 (7)
C9—N2—C8—O1	−179.3 (4)	O2—C12—C13—C14	178.8 (4)
C9—N2—C8—C11	−0.5 (6)	C4—C5—C6—C1	−0.4 (6)
C4—O1—C8—N2	−17.4 (6)	C7—C5—C6—C1	179.0 (4)
C4—O1—C8—C11	163.7 (4)	C22—O5—C21—O4A	6.3 (7)
N3—C10—C11—C8	−2.8 (6)	C22—O5—C21—C18	175.2 (5)
O2—C10—C11—C8	177.6 (4)	C19—C18—C21—O5	178.4 (4)
N2—C8—C11—C10	2.4 (6)	C17—C18—C21—O5	−5.2 (7)
O1—C8—C11—C10	−178.8 (4)	C19—C18—C21—O4A	−13.7 (8)
C16—C17—C12—C13	−2.5 (7)	C17—C18—C21—O4A	162.7 (6)
C18—C17—C12—C13	179.4 (4)	C12—C13—C14—C15	−0.7 (8)
C16—C17—C12—O2	−178.7 (4)	C20—O3—C19—O4	11.1 (9)
C18—C17—C12—O2	3.2 (6)	C20—O3—C19—C18	−173.6 (5)
C10—O2—C12—C13	101.8 (5)	C21—C18—C19—O4	−13.3 (8)
C10—O2—C12—C17	−81.7 (5)	C17—C18—C19—O4	170.4 (6)
C12—C17—C18—C19	−65.7 (6)	C21—C18—C19—O3	171.9 (4)
C16—C17—C18—C19	116.2 (5)	C17—C18—C19—O3	−4.5 (7)
C12—C17—C18—C21	118.1 (5)	C13—C14—C15—C16	−0.7 (8)
C16—C17—C18—C21	−59.9 (6)	C8—N2—C9—N3	−1.1 (8)
C8—O1—C4—C3	112.7 (4)	C10—N3—C9—N2	0.7 (8)
C8—O1—C4—C5	−73.5 (5)	C14—C15—C16—C17	0.6 (8)
C6—C5—C4—C3	1.4 (6)	C12—C17—C16—C15	1.0 (7)
C7—C5—C4—C3	−178.0 (4)	C18—C17—C16—C15	179.2 (4)
C6—C5—C4—O1	−172.2 (4)	C5—C6—C1—C2	−0.8 (7)
C7—C5—C4—O1	8.4 (6)	C3—C2—C1—C6	1.0 (7)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₃O₅
M_r	402.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	28.946 (6), 10.803 (2), 13.302 (3)
β (°)	94.61 (3)
V (Å³)	4146.1 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.08 × 0.07 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997a)
T_min, T_max	0.948, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	9000, 2169, 1733
R_int	0.055
θ_max (°)	20.8
(sin θ/λ)_max (Å⁻¹)	0.500

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.220, 1.14
No. of reflections	2169
No. of parameters	283
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997b), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

(2E)-Methyl 2-{2-[6-(2-cyano­phen­oxy)pyrimidin-4-yl­oxy]phen­yl}-3-methoxy­acrylate

Supporting information

Key indicators

checkCIF/PLATON results

(2E)-Methyl 2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate