5-{2-[3-(4-Methoxy­phenyl)-4,5-di­hydro­isoxazol-5-yl]­vinyl}-3-p-tolyl­isoxazole

The title compound, C₂₂H₂₀N₂O₃, displays a trans configuration with respect to the olefinic link. The isoxazole and benzene rings are slightly twisted towards each other.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.113
• Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.6491
            Proportion of unique data used    0.7170
            Ratio reflections to parameters   6.7090
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.71
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               2283
           Count of symmetry unique reflns         2304
           Completeness (_total/calc)             99.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku/MSC and Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C22H20N2O3	F(000) = 760.00
Mr = 360.41	Dx = 1.274 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2c -2ac	Cell parameters from 18400 reflections
a = 9.9819 (2) Å	θ = 2.2–27.4°
b = 22.3639 (4) Å	µ = 0.09 mm^−1
c = 8.4150 (1) Å	T = 296 K
V = 1878.52 (6) Å^3	Platelet, yellow
Z = 4	0.45 × 0.34 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.032
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −12→12
15501 measured reflections	k = −29→29
2283 independent reflections	l = −9→10
1257 reflections with F^2 > 2.0σ(F^2)

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[0.001Fo^2 + 0.76σ^2(Fo)]/(4Fo^2)
wR(F^2) = 0.113	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.24 e Å^−3
1637 reflections	Δρmin = −0.34 e Å^−3
244 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 1.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-fact

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9390 (2)	0.28823 (9)	0.3996 (3)	0.0821 (8)
O2	1.0014 (2)	0.4842 (1)	0.1209 (3)	0.0855 (8)
O3	0.8800 (2)	0.79107 (9)	0.5089 (3)	0.0778 (7)
N1	0.9517 (3)	0.2276 (1)	0.4441 (3)	0.0812 (9)
N2	1.0124 (2)	0.5452 (1)	0.1636 (3)	0.0751 (9)
C1	0.8815 (5)	−0.0614 (1)	0.3767 (6)	0.122 (2)
C2	0.8840 (4)	0.0061 (1)	0.3626 (4)	0.082 (1)
C3	0.9774 (4)	0.0398 (2)	0.4437 (5)	0.089 (1)
C4	0.9797 (3)	0.1014 (1)	0.4326 (4)	0.080 (1)
C5	0.8882 (3)	0.1318 (1)	0.3400 (4)	0.0636 (8)
C6	0.7941 (3)	0.0980 (2)	0.2571 (4)	0.084 (1)
C7	0.7932 (4)	0.0363 (2)	0.2716 (5)	0.096 (1)
C8	0.8903 (2)	0.1975 (1)	0.3314 (4)	0.0598 (8)
C9	0.8392 (3)	0.2361 (1)	0.2148 (4)	0.0664 (9)
C10	0.8724 (2)	0.2917 (1)	0.2608 (4)	0.0619 (9)
C11	0.8531 (3)	0.3506 (1)	0.1925 (4)	0.0666 (9)
C12	0.8990 (3)	0.4013 (1)	0.2519 (4)	0.0693 (9)
C13	0.8749 (3)	0.4604 (1)	0.1784 (4)	0.071 (1)
C14	0.8232 (2)	0.5087 (1)	0.2915 (4)	0.0678 (9)
C15	0.9164 (2)	0.5592 (1)	0.2564 (3)	0.0577 (8)
C16	0.9052 (2)	0.6193 (1)	0.3237 (3)	0.0567 (8)
C17	0.9904 (2)	0.6657 (1)	0.2760 (4)	0.0656 (9)
C18	0.9783 (3)	0.7219 (1)	0.3394 (4)	0.069 (1)
C19	0.8827 (3)	0.7335 (1)	0.4545 (4)	0.0630 (9)
C20	0.7987 (3)	0.6888 (1)	0.5044 (4)	0.0674 (9)
C21	0.8103 (3)	0.6323 (1)	0.4392 (4)	0.0690 (9)
C22	0.7923 (3)	0.8035 (1)	0.6396 (4)	0.082 (1)
H1	0.8678	−0.0717	0.4911	0.146*
H2	0.8062	−0.0781	0.3122	0.146*
H3	0.9682	−0.0787	0.3390	0.146*
H4	1.0466	0.0186	0.5087	0.107*
H5	1.0483	0.1251	0.4920	0.096*
H6	0.7270	0.1196	0.1901	0.101*
H7	0.7241	0.0124	0.2134	0.116*
H8	0.7870	0.2243	0.1184	0.080*
H9	0.8007	0.3533	0.0914	0.080*
H10	0.9538	0.3993	0.3512	0.083*
H11	0.8107	0.4560	0.0879	0.085*
H12	0.7275	0.5200	0.2733	0.081*
H13	0.8348	0.4949	0.4037	0.081*
H14	1.0600	0.6572	0.1935	0.079*
H15	1.0394	0.7546	0.3030	0.083*
H16	0.7291	0.6974	0.5868	0.081*
H17	0.7482	0.5996	0.4732	0.083*
H18	0.7978	0.8468	0.6687	0.098*
H19	0.6982	0.7935	0.6085	0.098*
H20	0.8194	0.7785	0.7327	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.103 (1)	0.071 (2)	0.072 (1)	0.005 (1)	−0.024 (1)	−0.010 (1)
O2	0.087 (1)	0.082 (2)	0.088 (2)	−0.001 (1)	0.029 (1)	−0.006 (1)
O3	0.084 (1)	0.069 (2)	0.080 (2)	0.002 (1)	0.007 (1)	0.011 (1)
N1	0.103 (2)	0.069 (2)	0.071 (2)	0.001 (1)	−0.020 (2)	−0.004 (1)
N2	0.075 (1)	0.076 (2)	0.074 (2)	0.006 (1)	0.019 (1)	0.003 (1)
C1	0.157 (4)	0.078 (3)	0.130 (4)	−0.029 (2)	0.021 (3)	−0.006 (2)
C2	0.093 (2)	0.075 (2)	0.078 (2)	−0.017 (2)	0.018 (2)	−0.003 (2)
C3	0.097 (2)	0.080 (2)	0.090 (3)	−0.008 (2)	−0.010 (2)	0.010 (2)
C4	0.084 (2)	0.070 (2)	0.086 (2)	−0.013 (2)	−0.015 (2)	−0.003 (2)
C5	0.060 (1)	0.076 (2)	0.055 (2)	−0.005 (2)	0.006 (1)	−0.005 (2)
C6	0.084 (2)	0.093 (3)	0.076 (2)	−0.014 (2)	−0.012 (2)	−0.002 (2)
C7	0.107 (3)	0.089 (3)	0.094 (3)	−0.033 (2)	−0.006 (2)	−0.015 (2)
C8	0.049 (1)	0.074 (2)	0.056 (2)	−0.003 (1)	0.005 (1)	−0.006 (2)
C9	0.059 (1)	0.080 (2)	0.060 (2)	−0.008 (1)	−0.005 (1)	−0.007 (2)
C10	0.050 (1)	0.081 (2)	0.055 (2)	0.004 (1)	−0.000 (1)	−0.005 (2)
C11	0.060 (1)	0.081 (2)	0.059 (2)	0.008 (1)	−0.000 (1)	0.004 (2)
C12	0.064 (1)	0.076 (2)	0.068 (2)	0.003 (1)	−0.013 (1)	0.003 (2)
C13	0.071 (2)	0.078 (2)	0.063 (2)	−0.000 (1)	−0.013 (2)	0.005 (2)
C14	0.057 (1)	0.073 (2)	0.073 (2)	−0.002 (1)	0.003 (1)	0.009 (2)
C15	0.049 (1)	0.075 (2)	0.049 (1)	0.008 (1)	−0.001 (1)	0.017 (1)
C16	0.048 (1)	0.072 (2)	0.050 (2)	0.009 (1)	0.000 (1)	0.016 (1)
C17	0.052 (1)	0.085 (2)	0.060 (2)	−0.000 (1)	0.010 (1)	0.013 (2)
C18	0.062 (2)	0.075 (2)	0.071 (2)	−0.008 (1)	0.010 (2)	0.017 (2)
C19	0.059 (1)	0.064 (2)	0.065 (2)	0.008 (1)	−0.001 (2)	0.016 (1)
C20	0.062 (2)	0.066 (2)	0.074 (2)	0.007 (1)	0.021 (1)	0.019 (2)
C21	0.060 (1)	0.068 (2)	0.078 (2)	0.002 (1)	0.017 (2)	0.020 (2)
C22	0.082 (2)	0.080 (2)	0.083 (2)	0.012 (2)	0.008 (2)	−0.001 (2)

Geometric parameters (Å, º)

O1—N1	1.412 (3)	C9—H8	1.000
O1—C10	1.346 (3)	C10—C11	1.450 (4)
O2—N2	1.416 (3)	C11—C12	1.321 (4)
O2—C13	1.453 (3)	C11—H9	1.000
O3—C19	1.366 (3)	C12—C13	1.478 (4)
O3—C22	1.433 (4)	C12—H10	1.000
N1—C8	1.315 (4)	C13—C14	1.530 (4)
N2—C15	1.275 (3)	C13—H11	1.000
C1—C2	1.514 (4)	C14—C15	1.493 (4)
C1—H1	1.000	C14—H12	1.000
C1—H2	1.000	C14—H13	1.000
C1—H3	1.000	C15—C16	1.463 (4)
C2—C3	1.379 (5)	C16—C17	1.400 (4)
C2—C7	1.365 (5)	C16—C21	1.388 (4)
C3—C4	1.382 (4)	C17—C18	1.372 (4)
C3—H4	1.000	C17—H14	1.000
C4—C5	1.379 (4)	C18—C19	1.384 (4)
C4—H5	1.000	C18—H15	1.000
C5—C6	1.392 (4)	C19—C20	1.370 (4)
C5—C8	1.472 (4)	C20—C21	1.384 (4)
C6—C7	1.386 (5)	C20—H16	1.000
C6—H6	1.000	C21—H17	1.000
C7—H7	1.000	C22—H18	1.000
C8—C9	1.403 (4)	C22—H19	1.000
C9—C10	1.345 (4)	C22—H20	1.000
N1—O1—C10	109.3 (2)	C11—C12—H10	117.9
N2—O2—C13	109.62 (19)	C13—C12—H10	118.6
C19—O3—C22	116.9 (2)	O2—C13—C12	109.0 (2)
O1—N1—C8	105.0 (2)	O2—C13—C14	104.0 (2)
O2—N2—C15	109.5 (2)	C12—C13—C14	115.2 (3)
C2—C1—H1	108.0	O2—C13—H11	109.9
C2—C1—H2	110.0	C12—C13—H11	109.6
H1—C1—H2	109.5	C14—C13—H11	109.1
C2—C1—H3	110.4	C13—C14—C15	101.6 (2)
H1—C1—H3	109.5	C13—C14—H12	113.9
H2—C1—H3	109.5	C15—C14—H12	112.0
C1—C2—C3	121.1 (4)	C13—C14—H13	109.3
C1—C2—C7	121.7 (3)	C15—C14—H13	110.4
C3—C2—C7	117.2 (3)	H12—C14—H13	109.5
C2—C3—C4	121.5 (4)	N2—C15—C14	113.8 (3)
C2—C3—H4	118.6	N2—C15—C16	121.3 (2)
C4—C3—H4	119.9	C14—C15—C16	124.8 (2)
C3—C4—C5	121.2 (3)	C15—C16—C17	121.5 (2)
C3—C4—H5	120.4	C15—C16—C21	121.0 (2)
C5—C4—H5	118.4	C17—C16—C21	117.5 (3)
C4—C5—C6	117.6 (3)	C16—C17—C18	120.9 (3)
C4—C5—C8	120.6 (2)	C16—C17—H14	118.7
C6—C5—C8	121.8 (3)	C18—C17—H14	120.4
C5—C6—C7	120.0 (3)	C17—C18—C19	120.3 (3)
C5—C6—H6	118.2	C17—C18—H15	119.8
C7—C6—H6	121.7	C19—C18—H15	119.9
C2—C7—C6	122.5 (3)	O3—C19—C18	115.1 (3)
C2—C7—H7	118.0	O3—C19—C20	124.9 (3)
C6—C7—H7	119.5	C18—C19—C20	120.0 (3)
N1—C8—C5	118.9 (3)	C19—C20—C21	119.6 (3)
N1—C8—C9	111.0 (3)	C19—C20—H16	119.9
C5—C8—C9	130.1 (3)	C21—C20—H16	120.5
C8—C9—C10	106.2 (3)	C16—C21—C20	121.7 (3)
C8—C9—H8	126.5	C16—C21—H17	118.1
C10—C9—H8	127.3	C20—C21—H17	120.2
O1—C10—C9	108.5 (3)	O3—C22—H18	110.0
O1—C10—C11	117.6 (3)	O3—C22—H19	109.2
C9—C10—C11	133.9 (3)	H18—C22—H19	109.5
C10—C11—C12	125.7 (3)	O3—C22—H20	109.1
C10—C11—H9	117.5	H18—C22—H20	109.5
C12—C11—H9	116.8	H19—C22—H20	109.5
C11—C12—C13	123.5 (3)
C10—O1—N1—C8	−1.0 (4)	C5—C8—C9—C10	−177.6 (4)
N1—O1—C10—C9	1.1 (4)	C8—C9—C10—O1	−0.8 (4)
N1—O1—C10—C11	−178.0 (3)	C8—C9—C10—C11	178.1 (4)
C13—O2—N2—C15	8.1 (5)	O1—C10—C11—C12	2.4 (6)
N2—O2—C13—C12	−135.4 (3)	C9—C10—C11—C12	−176.5 (4)
N2—O2—C13—C14	−12.1 (4)	C10—C11—C12—C13	−179.2 (4)
C22—O3—C19—C18	−173.7 (4)	C11—C12—C13—O2	−113.2 (4)
C22—O3—C19—C20	7.0 (6)	C11—C12—C13—C14	130.5 (4)
O1—N1—C8—C5	178.5 (3)	O2—C13—C14—C15	11.0 (4)
O1—N1—C8—C9	0.5 (4)	C12—C13—C14—C15	130.2 (4)
O2—N2—C15—C14	−0.2 (4)	C13—C14—C15—N2	−7.2 (5)
O2—N2—C15—C16	178.0 (3)	C13—C14—C15—C16	174.8 (4)
C1—C2—C3—C4	−179.4 (5)	N2—C15—C16—C17	7.0 (6)
C7—C2—C3—C4	−0.3 (8)	N2—C15—C16—C21	−172.2 (3)
C1—C2—C7—C6	−179.9 (5)	C14—C15—C16—C17	−175.1 (3)
C3—C2—C7—C6	1.1 (8)	C14—C15—C16—C21	5.7 (6)
C2—C3—C4—C5	0.1 (7)	C15—C16—C17—C18	179.6 (3)
C3—C4—C5—C6	−0.5 (7)	C21—C16—C17—C18	−1.2 (6)
C3—C4—C5—C8	179.0 (4)	C15—C16—C21—C20	179.8 (3)
C4—C5—C6—C7	1.1 (7)	C17—C16—C21—C20	0.6 (6)
C8—C5—C6—C7	−178.3 (4)	C16—C17—C18—C19	1.3 (6)
C4—C5—C8—N1	−19.5 (6)	C17—C18—C19—O3	179.9 (3)
C4—C5—C8—C9	158.1 (4)	C17—C18—C19—C20	−0.7 (6)
C6—C5—C8—N1	160.0 (4)	O3—C19—C20—C21	179.4 (3)
C6—C5—C8—C9	−22.4 (7)	C18—C19—C20—C21	0.1 (6)
C5—C6—C7—C2	−1.5 (7)	C19—C20—C21—C16	−0.0 (6)
N1—C8—C9—C10	0.2 (5)