(Z)-3-(3,4-Dimeth­oxy­phen­yl)-3-(4-fluoro­phen­yl)-1-morpholino­prop-2-en-1-one

Chai, B.; Liu, C.

doi:10.1107/S1600536811022008

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1780

doi:10.1107/S1600536811022008

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(Z)-3-(3,4-Dimethoxyphenyl)-3-(4-fluorophenyl)-1-morpholinoprop-2-en-1-one

Baoshan Chai ^a ^* and Changling Liu ^a

^aState Key Laboratory of the Discovery and Development of Novel Pesticides, Shenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
^*Correspondence e-mail: chaibaoshan@163.com

(Received 10 May 2011; accepted 7 June 2011; online 22 June 2011)

The title compound, C₂₁H₂₂FNO₄, is an isomer of flumorph (systematic name 4-[3-(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-1-oxo-2-propenyl]morpholine), which was developed by Shenyang research institute of chemical industry and used as fungicide. The molecule adopts a Z configuration about the C=C double bond. The dihedral angle between the two benzene rings is 73.45 (11)°.

Related literature

The title compound is an isomer of flumorph. For background to the use of flumorph as a fungicide, see: Liu et al. (2002 ). For the synthesis, see: Li et al. (2000 ). For the use of flumorph, see: Liu (2000 ).

Experimental

Crystal data

C₂₁H₂₂FNO₄
M_r = 371.40
Monoclinic, P 2₁ /c
a = 6.4963 (18) Å
b = 13.306 (4) Å
c = 20.890 (6) Å
β = 95.651 (4)°
V = 1797.0 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002) T_min = 0.980, T_max = 0.990
15064 measured reflections
3171 independent reflections
2713 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.115
S = 1.19
3171 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O2ⁱ	0.99	2.57	3.279 (3)	129
C11—H11⋯O2ⁱⁱ	0.95	2.58	3.478 (3)	158
C15—H15⋯O3ⁱⁱⁱ	0.95	2.38	3.216 (3)	147
C21—H21A⋯O3^iv	0.99	2.42	3.105 (3)	125
C8—H8B⋯O4^v	0.98	2.55	2.983 (3)	106
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x+1, y, z; (v) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2002).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536811022008/zk2011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022008/zk2011Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022008/zk2011Isup3.cml

checkCIF report

Comment top

Flumorph is a commercial fungicide, it was discovered in 1994. As reported (Li et al., 2000), there are two isomers in the product. In this paper, we report the crystal structure of one of the isomer. In the crystal structure of the title compound, the molecule adopts a Z configuration about the C=C double bond and The dihedral angle between the two benzene rings is 73.45 (11)°.

Related literature top

The title compound is an isomer of flumorph. For background to the use of flumorph as a fungicide, see: Liu et al. (2002). For the synthesis, see: Li et al. (2000). For the uses of flumorph, see: Liu (2000).

Experimental top

The title compound was synthesized by (3,4-dimethoxyphenyl)(4-fluorophenyl)methanone with 1-morpholinoethanone under basic condition in toluene. The crude products were purified by recrystallization from methanol and then grown from DMF to afford colorless single crystals suitable for X-ray diffraction. To a solution of sodium tert-butoxide(0.15 mol) in toluene(280 ml) and tert-butanol(30 ml) was added the (3,4-Dmethoxyphenyl)(4-fluorophenyl)methanone (26 g, 0.1 mol) at room tempreture. The reaction mixture was heated to reflux for 6 h, a solution of 1-morpholinoethanone(0.15 mol) in toluene(20 ml) was added over 1 h. The tert-butanol was distilled off at the same time, then the mixture was washed with water, the organic extracts were dried over magnesium sulfate and concentrated. Afford the tittle product compound as a white solid(31.5 g, 88%).

Anal. Calcd for C₂₁H₂₂FNO₄: C, 67.91; H, 5.97; N, 3.77. Found: C, 67.93; H, 5.94; N, 3.75. ¹H NMR(CDCl₃): 3.19 (m, 2H, morpholine-CH₂), 3.29 (m, 2H, morpholine-CH₂), 3.52 (m, 4H, morpholine-2CH₂), 3.82 (s, 3H, OCH₃), 3.90 (s, 3H, OCH₃), 6.24 (s, 1H, CH), 6.77 (s, 1H, Ph—H), 6.81 (s, 1H, Ph—H), 6.82 (s, 1H, Ph—H), 7.07 (m, 2H, Ph-2H), 7.28 (m, 2H, Ph-2H).

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2002).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.

(Z)-3-(3,4-Dimethoxyphenyl)-3-(4-fluorophenyl)-1-morpholinoprop-2-en-1-one top

Crystal data top

C₂₁H₂₂FNO₄	F(000) = 784
M_r = 371.40	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5162 reflections
a = 6.4963 (18) Å	θ = 1.8–27.9°
b = 13.306 (4) Å	µ = 0.10 mm⁻¹
c = 20.890 (6) Å	T = 113 K
β = 95.651 (4)°	Prism, colorless
V = 1797.0 (9) Å³	0.20 × 0.18 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3171 independent reflections
Radiation source: rotating anode	2713 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.066
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω and ϕ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	k = −15→15
T_min = 0.980, T_max = 0.990	l = −24→24
15064 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0358P)² + 0.3441P] where P = (F_o² + 2F_c²)/3
3171 reflections	(Δ/σ)_max = 0.004
246 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₂₂FNO₄	V = 1797.0 (9) Å³
M_r = 371.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.4963 (18) Å	µ = 0.10 mm⁻¹
b = 13.306 (4) Å	T = 113 K
c = 20.890 (6) Å	0.20 × 0.18 × 0.10 mm
β = 95.651 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3171 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	2713 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.066
15064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.19	Δρ_max = 0.18 e Å⁻³
3171 reflections	Δρ_min = −0.23 e Å⁻³
246 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
F1	0.8136 (2)	0.40799 (13)	−0.02485 (8)	0.0508 (5)
O1	0.0240 (2)	0.26719 (12)	0.34490 (8)	0.0267 (4)
O2	0.3744 (2)	0.32110 (12)	0.40261 (8)	0.0248 (4)
O3	0.4465 (2)	0.66020 (12)	0.32079 (8)	0.0283 (4)
O4	1.0853 (2)	0.61491 (12)	0.46137 (8)	0.0264 (4)
N1	0.7861 (3)	0.63993 (14)	0.35473 (9)	0.0206 (5)
C1	0.1421 (3)	0.32636 (17)	0.30920 (12)	0.0214 (5)
C2	0.3331 (3)	0.35649 (17)	0.34125 (11)	0.0194 (5)
C3	0.4633 (3)	0.41694 (16)	0.31010 (11)	0.0196 (5)
H3	0.5914	0.4374	0.3321	0.024*
C4	0.4115 (3)	0.44909 (17)	0.24662 (11)	0.0196 (5)
C5	0.2246 (3)	0.41741 (17)	0.21506 (11)	0.0219 (6)
H5	0.1879	0.4370	0.1717	0.026*
C6	0.0898 (3)	0.35698 (17)	0.24639 (11)	0.0224 (6)
H6	−0.0386	0.3368	0.2244	0.027*
C7	−0.1556 (3)	0.21977 (18)	0.31262 (12)	0.0282 (6)
H7A	−0.2509	0.2713	0.2938	0.042*
H7B	−0.2247	0.1797	0.3436	0.042*
H7C	−0.1139	0.1759	0.2785	0.042*
C8	0.5605 (3)	0.35492 (19)	0.43833 (12)	0.0263 (6)
H8A	0.6800	0.3322	0.4170	0.039*
H8B	0.5687	0.3273	0.4820	0.039*
H8C	0.5603	0.4285	0.4404	0.039*
C9	0.5592 (3)	0.51373 (17)	0.21513 (11)	0.0204 (5)
C10	0.6104 (3)	0.48695 (17)	0.14952 (12)	0.0216 (5)
C11	0.6589 (4)	0.56046 (19)	0.10521 (12)	0.0284 (6)
H11	0.6452	0.6295	0.1155	0.034*
C12	0.7261 (4)	0.5340 (2)	0.04685 (13)	0.0343 (7)
H12	0.7575	0.5842	0.0170	0.041*
C13	0.7468 (4)	0.4343 (2)	0.03280 (12)	0.0335 (7)
C14	0.6999 (4)	0.3593 (2)	0.07389 (12)	0.0296 (6)
H14	0.7154	0.2907	0.0628	0.036*
C15	0.6292 (3)	0.38614 (18)	0.13209 (12)	0.0237 (6)
H15	0.5929	0.3350	0.1606	0.028*
C16	0.6596 (3)	0.59017 (17)	0.24583 (11)	0.0206 (5)
H16	0.7663	0.6210	0.2248	0.025*
C17	0.6207 (3)	0.63187 (17)	0.31001 (12)	0.0206 (5)
C18	0.7732 (4)	0.69660 (18)	0.41400 (11)	0.0240 (6)
H18A	0.6262	0.7082	0.4205	0.029*
H18B	0.8403	0.7629	0.4104	0.029*
C19	0.8775 (3)	0.64070 (19)	0.47103 (11)	0.0253 (6)
H19A	0.8772	0.6831	0.5100	0.030*
H19B	0.7987	0.5787	0.4782	0.030*
C20	1.0895 (4)	0.55327 (19)	0.40550 (11)	0.0248 (6)
H20A	1.0116	0.4906	0.4114	0.030*
H20B	1.2344	0.5348	0.4001	0.030*
C21	0.9958 (3)	0.60684 (18)	0.34551 (12)	0.0236 (6)
H21A	1.0820	0.6656	0.3366	0.028*
H21B	0.9918	0.5608	0.3082	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0442 (10)	0.0796 (13)	0.0310 (10)	−0.0077 (9)	0.0152 (8)	−0.0142 (9)
O1	0.0226 (9)	0.0285 (10)	0.0285 (10)	−0.0089 (8)	0.0010 (8)	−0.0016 (8)
O2	0.0257 (9)	0.0275 (10)	0.0201 (10)	−0.0066 (8)	−0.0029 (7)	0.0026 (7)
O3	0.0192 (9)	0.0276 (10)	0.0380 (11)	0.0026 (8)	0.0021 (8)	−0.0069 (8)
O4	0.0256 (9)	0.0316 (10)	0.0213 (10)	0.0032 (8)	−0.0014 (7)	−0.0037 (8)
N1	0.0176 (10)	0.0233 (11)	0.0206 (11)	0.0028 (9)	−0.0003 (9)	−0.0033 (9)
C1	0.0205 (13)	0.0187 (12)	0.0256 (14)	0.0001 (10)	0.0049 (11)	−0.0027 (10)
C2	0.0230 (13)	0.0177 (12)	0.0170 (13)	0.0029 (10)	−0.0009 (10)	−0.0014 (10)
C3	0.0188 (12)	0.0163 (12)	0.0227 (14)	−0.0014 (10)	−0.0034 (10)	−0.0037 (10)
C4	0.0202 (13)	0.0180 (12)	0.0202 (13)	0.0003 (10)	0.0000 (10)	−0.0029 (10)
C5	0.0261 (14)	0.0204 (13)	0.0185 (13)	0.0011 (11)	−0.0018 (11)	−0.0009 (10)
C6	0.0184 (12)	0.0228 (13)	0.0249 (14)	−0.0011 (11)	−0.0040 (11)	−0.0037 (11)
C7	0.0211 (13)	0.0285 (15)	0.0354 (16)	−0.0043 (11)	0.0050 (12)	−0.0068 (12)
C8	0.0268 (14)	0.0300 (14)	0.0208 (14)	−0.0030 (12)	−0.0042 (11)	0.0018 (11)
C9	0.0186 (12)	0.0199 (13)	0.0217 (14)	0.0028 (10)	−0.0029 (10)	0.0010 (10)
C10	0.0174 (12)	0.0236 (13)	0.0228 (14)	−0.0013 (10)	−0.0035 (10)	0.0020 (11)
C11	0.0266 (14)	0.0302 (15)	0.0272 (15)	−0.0040 (12)	−0.0028 (12)	0.0035 (12)
C12	0.0297 (15)	0.0480 (18)	0.0247 (15)	−0.0094 (14)	0.0005 (12)	0.0066 (13)
C13	0.0254 (15)	0.0548 (19)	0.0206 (15)	−0.0055 (13)	0.0039 (11)	−0.0094 (13)
C14	0.0252 (14)	0.0347 (15)	0.0285 (15)	−0.0015 (12)	0.0008 (12)	−0.0095 (12)
C15	0.0231 (14)	0.0243 (14)	0.0229 (14)	−0.0033 (11)	−0.0022 (11)	−0.0015 (11)
C16	0.0175 (12)	0.0233 (13)	0.0205 (13)	0.0010 (11)	0.0000 (10)	0.0023 (11)
C17	0.0187 (13)	0.0148 (12)	0.0283 (15)	−0.0019 (10)	0.0020 (11)	0.0002 (10)
C18	0.0254 (14)	0.0253 (14)	0.0210 (14)	0.0034 (11)	0.0015 (11)	−0.0039 (11)
C19	0.0264 (14)	0.0306 (14)	0.0190 (14)	0.0023 (12)	0.0030 (11)	−0.0033 (11)
C20	0.0239 (13)	0.0283 (14)	0.0218 (14)	0.0044 (11)	0.0007 (11)	−0.0046 (11)
C21	0.0194 (13)	0.0289 (14)	0.0228 (14)	0.0032 (11)	0.0029 (11)	−0.0025 (11)

Geometric parameters (Å, º) top

F1—C13	1.365 (3)	C8—H8C	0.9800
O1—C1	1.370 (3)	C9—C16	1.338 (3)
O1—C7	1.435 (3)	C9—C10	1.485 (3)
O2—C2	1.367 (3)	C10—C15	1.398 (3)
O2—C8	1.430 (3)	C10—C11	1.404 (3)
O3—C17	1.235 (3)	C11—C12	1.380 (3)
O4—C19	1.427 (3)	C11—H11	0.9500
O4—C20	1.429 (3)	C12—C13	1.368 (4)
N1—C17	1.357 (3)	C12—H12	0.9500
N1—C18	1.459 (3)	C13—C14	1.370 (4)
N1—C21	1.462 (3)	C14—C15	1.388 (3)
C1—C6	1.384 (3)	C14—H14	0.9500
C1—C2	1.409 (3)	C15—H15	0.9500
C2—C3	1.376 (3)	C16—C17	1.495 (3)
C3—C4	1.402 (3)	C16—H16	0.9500
C3—H3	0.9500	C18—C19	1.508 (3)
C4—C5	1.389 (3)	C18—H18A	0.9900
C4—C9	1.489 (3)	C18—H18B	0.9900
C5—C6	1.398 (3)	C19—H19A	0.9900
C5—H5	0.9500	C19—H19B	0.9900
C6—H6	0.9500	C20—C21	1.516 (3)
C7—H7A	0.9800	C20—H20A	0.9900
C7—H7B	0.9800	C20—H20B	0.9900
C7—H7C	0.9800	C21—H21A	0.9900
C8—H8A	0.9800	C21—H21B	0.9900
C8—H8B	0.9800

C1—O1—C7	118.03 (19)	C10—C11—H11	119.5
C2—O2—C8	117.29 (17)	C13—C12—C11	118.9 (2)
C19—O4—C20	110.37 (17)	C13—C12—H12	120.6
C17—N1—C18	121.16 (18)	C11—C12—H12	120.6
C17—N1—C21	124.8 (2)	F1—C13—C12	119.0 (2)
C18—N1—C21	113.55 (18)	F1—C13—C14	118.4 (2)
O1—C1—C6	125.9 (2)	C12—C13—C14	122.6 (2)
O1—C1—C2	114.8 (2)	C13—C14—C15	118.4 (2)
C6—C1—C2	119.3 (2)	C13—C14—H14	120.8
O2—C2—C3	124.9 (2)	C15—C14—H14	120.8
O2—C2—C1	115.4 (2)	C14—C15—C10	121.3 (2)
C3—C2—C1	119.7 (2)	C14—C15—H15	119.4
C2—C3—C4	121.6 (2)	C10—C15—H15	119.4
C2—C3—H3	119.2	C9—C16—C17	126.5 (2)
C4—C3—H3	119.2	C9—C16—H16	116.8
C5—C4—C3	118.3 (2)	C17—C16—H16	116.8
C5—C4—C9	122.5 (2)	O3—C17—N1	121.9 (2)
C3—C4—C9	119.3 (2)	O3—C17—C16	121.1 (2)
C4—C5—C6	120.7 (2)	N1—C17—C16	117.03 (19)
C4—C5—H5	119.6	N1—C18—C19	110.90 (19)
C6—C5—H5	119.6	N1—C18—H18A	109.5
C1—C6—C5	120.4 (2)	C19—C18—H18A	109.5
C1—C6—H6	119.8	N1—C18—H18B	109.5
C5—C6—H6	119.8	C19—C18—H18B	109.5
O1—C7—H7A	109.5	H18A—C18—H18B	108.0
O1—C7—H7B	109.5	O4—C19—C18	111.38 (19)
H7A—C7—H7B	109.5	O4—C19—H19A	109.4
O1—C7—H7C	109.5	C18—C19—H19A	109.4
H7A—C7—H7C	109.5	O4—C19—H19B	109.4
H7B—C7—H7C	109.5	C18—C19—H19B	109.4
O2—C8—H8A	109.5	H19A—C19—H19B	108.0
O2—C8—H8B	109.5	O4—C20—C21	111.52 (19)
H8A—C8—H8B	109.5	O4—C20—H20A	109.3
O2—C8—H8C	109.5	C21—C20—H20A	109.3
H8A—C8—H8C	109.5	O4—C20—H20B	109.3
H8B—C8—H8C	109.5	C21—C20—H20B	109.3
C16—C9—C10	118.8 (2)	H20A—C20—H20B	108.0
C16—C9—C4	122.2 (2)	N1—C21—C20	109.63 (19)
C10—C9—C4	118.8 (2)	N1—C21—H21A	109.7
C15—C10—C11	117.8 (2)	C20—C21—H21A	109.7
C15—C10—C9	120.2 (2)	N1—C21—H21B	109.7
C11—C10—C9	121.8 (2)	C20—C21—H21B	109.7
C12—C11—C10	121.1 (2)	H21A—C21—H21B	108.2
C12—C11—H11	119.5

C7—O1—C1—C6	9.9 (3)	C9—C10—C11—C12	173.5 (2)
C7—O1—C1—C2	−169.79 (19)	C10—C11—C12—C13	−0.5 (4)
C8—O2—C2—C3	4.3 (3)	C11—C12—C13—F1	−179.9 (2)
C8—O2—C2—C1	−176.16 (19)	C11—C12—C13—C14	1.2 (4)
O1—C1—C2—O2	1.1 (3)	F1—C13—C14—C15	−179.1 (2)
C6—C1—C2—O2	−178.6 (2)	C12—C13—C14—C15	−0.2 (4)
O1—C1—C2—C3	−179.38 (19)	C13—C14—C15—C10	−1.5 (4)
C6—C1—C2—C3	0.9 (3)	C11—C10—C15—C14	2.1 (3)
O2—C2—C3—C4	179.0 (2)	C9—C10—C15—C14	−172.5 (2)
C1—C2—C3—C4	−0.5 (3)	C10—C9—C16—C17	176.1 (2)
C2—C3—C4—C5	−0.7 (3)	C4—C9—C16—C17	−9.4 (4)
C2—C3—C4—C9	−179.5 (2)	C18—N1—C17—O3	−9.7 (3)
C3—C4—C5—C6	1.5 (3)	C21—N1—C17—O3	179.2 (2)
C9—C4—C5—C6	−179.8 (2)	C18—N1—C17—C16	168.3 (2)
O1—C1—C6—C5	−179.8 (2)	C21—N1—C17—C16	−2.8 (3)
C2—C1—C6—C5	−0.2 (3)	C9—C16—C17—O3	−54.5 (3)
C4—C5—C6—C1	−1.0 (3)	C9—C16—C17—N1	127.5 (2)
C5—C4—C9—C16	138.5 (2)	C17—N1—C18—C19	137.0 (2)
C3—C4—C9—C16	−42.8 (3)	C21—N1—C18—C19	−51.0 (3)
C5—C4—C9—C10	−47.0 (3)	C20—O4—C19—C18	−59.3 (3)
C3—C4—C9—C10	131.7 (2)	N1—C18—C19—O4	54.2 (3)
C16—C9—C10—C15	137.8 (2)	C19—O4—C20—C21	60.3 (2)
C4—C9—C10—C15	−36.9 (3)	C17—N1—C21—C20	−137.1 (2)
C16—C9—C10—C11	−36.6 (3)	C18—N1—C21—C20	51.2 (3)
C4—C9—C10—C11	148.7 (2)	O4—C20—C21—N1	−55.5 (3)
C15—C10—C11—C12	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O2ⁱ	0.99	2.57	3.279 (3)	129
C11—H11···O2ⁱⁱ	0.95	2.58	3.478 (3)	158
C15—H15···O3ⁱⁱⁱ	0.95	2.38	3.216 (3)	147
C21—H21A···O3^iv	0.99	2.42	3.105 (3)	125
C8—H8B···O4^v	0.98	2.55	2.983 (3)	106

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂FNO₄
M_r	371.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	6.4963 (18), 13.306 (4), 20.890 (6)
β (°)	95.651 (4)
V (Å³)	1797.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2002)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	15064, 3171, 2713
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.115, 1.19
No. of reflections	3171
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2002).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O2ⁱ	0.99	2.57	3.279 (3)	128.6
C11—H11···O2ⁱⁱ	0.95	2.58	3.478 (3)	158.0
C15—H15···O3ⁱⁱⁱ	0.95	2.38	3.216 (3)	147.3
C21—H21A···O3^iv	0.99	2.42	3.105 (3)	125.4
C8—H8B···O4^v	0.98	2.55	2.983 (3)	106.4

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

Acknowledgements

This project was supported by the National Basic Research Program of China (973 Program 2010CB126105) and the National Key Technologies R&D Program (2011BAE06B05).

References

Li, Z., Liu, C. & Liu, W. (2000). US patent US6020332. Google Scholar
Liu, C. (2000). Proceedings of the Brighton Crop Protection Conference - Pests and diseases, p. 549. Alton, Hampshire, England: BCPC Publications. Google Scholar
Liu, C., Liu, W. & Li, Z. (2002). Chinese patent CN1385070. Google Scholar
Rigaku (2002). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1780

doi:10.1107/S1600536811022008

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(Z)-3-(3,4-Dimeth­­oxy­phen­yl)-3-(4-fluoro­phen­yl)-1-morpholino­prop-2-en-1-one

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Experimental

Crystal data

Data collection

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organic compounds

(Z)-3-(3,4-Dimethoxyphenyl)-3-(4-fluorophenyl)-1-morpholinoprop-2-en-1-one