Crystal structure of dimethomorph.

In the title compound, C21H22ClNO4 [systematic name: (E)-3-(4-chloro-phen-yl)-3-(3,4-di-meth-oxy-phen-yl)-1-(morpholin-4-yl)prop-2-en-1-one], which is the morpholine fungicide dimethomorph, the dihedral angles between the mean planes of the central chloro-phenyl and the terminal benzene and morpholine (r.m.s. deviation = 0.2233 Å) rings are 71.74 (6) and 63.65 (7)°, respectively. In the crystal, molecules are linked via C-H⋯O hydrogen bonds and weak Cl⋯π interactions [3.8539 (11) Å], forming a three-dimensional structure.

Related literature

For information on the fungicidal properties of the title compound, see: Xu et al. (2015 ▸). For related crystal structures, see: Chai & Liu (2011 ▸); Lu & Shi (2011 ▸).

Experimental

Crystal data

C21H22ClNO4

M = 387.84

Monoclinic,

a = 6.6238 (2) Å

b = 13.2232 (4) Å

c = 21.4810 (7) Å

β = 97.1674 (19)°

V = 1866.77 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.38 × 0.06 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.917, T max = 0.993

18090 measured reflections

4276 independent reflections

3119 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.133

S = 1.04

4276 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014735/hg5456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014735/hg5456Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015014735/hg5456fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

a . DOI: 10.1107/S2056989015014735/hg5456fig2.tif

Crystal packing viewed along the a axis. The inter­molecular inter­actions are shown as dashed lines.

CCDC reference: 1417163

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H22ClNO4	F(000) = 816
Mr = 387.84	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6238 (2) Å	Cell parameters from 3670 reflections
b = 13.2232 (4) Å	θ = 2.5–24.0°
c = 21.4810 (7) Å	µ = 0.23 mm−1
β = 97.1674 (19)°	T = 173 K
V = 1866.77 (10) Å3	Needle, colourless
Z = 4	0.38 × 0.06 × 0.03 mm

Bruker APEXII CCD diffractometer	3119 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.5°, θmin = 1.8°
Tmin = 0.917, Tmax = 0.993	h = −8→8
18090 measured reflections	k = −14→17
4276 independent reflections	l = −27→27

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.059P)2 + 0.6606P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4276 reflections	Δρmax = 0.27 e Å−3
246 parameters	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.31366 (10)	0.59912 (5)	0.47448 (3)	0.0574 (2)
O1	0.5956 (2)	0.38430 (11)	0.96279 (6)	0.0370 (4)
O2	−0.0418 (2)	0.34526 (10)	0.82830 (7)	0.0370 (4)
O3	−0.1413 (2)	0.67931 (10)	0.90317 (6)	0.0337 (3)
O4	−0.4849 (2)	0.73290 (10)	0.84142 (6)	0.0368 (4)
N1	0.2962 (2)	0.35718 (12)	0.85873 (7)	0.0281 (4)
C1	0.5023 (3)	0.38939 (15)	0.84994 (9)	0.0305 (4)
H1A	0.4969	0.4347	0.8131	0.037*
H1B	0.5855	0.3296	0.8421	0.037*
C2	0.5976 (3)	0.44402 (16)	0.90772 (9)	0.0347 (5)
H2A	0.7399	0.4617	0.9027	0.042*
H2B	0.5226	0.5078	0.9125	0.042*
C3	0.3918 (3)	0.35949 (17)	0.97178 (9)	0.0364 (5)
H3A	0.3150	0.4224	0.9772	0.044*
H3B	0.3928	0.3187	1.0104	0.044*
C4	0.2872 (3)	0.30099 (16)	0.91686 (9)	0.0335 (5)
H4A	0.3542	0.2345	0.9142	0.040*
H4B	0.1434	0.2890	0.9229	0.040*
C5	0.1286 (3)	0.37008 (13)	0.81674 (9)	0.0267 (4)
C6	0.1627 (3)	0.41177 (14)	0.75448 (9)	0.0277 (4)
H6	0.2683	0.3819	0.7346	0.033*
C7	0.0584 (3)	0.48755 (13)	0.72382 (9)	0.0263 (4)
C8	0.1046 (3)	0.51370 (14)	0.65975 (9)	0.0274 (4)
C9	0.1513 (3)	0.43952 (16)	0.61797 (9)	0.0354 (5)
H9	0.1412	0.3702	0.6289	0.043*
C10	0.2124 (3)	0.46527 (17)	0.56054 (10)	0.0411 (5)
H10	0.2424	0.4140	0.5321	0.049*
C11	0.2291 (3)	0.56604 (18)	0.54519 (10)	0.0378 (5)
C12	0.1811 (3)	0.64122 (16)	0.58492 (10)	0.0350 (5)
H12	0.1923	0.7103	0.5737	0.042*
C13	0.1159 (3)	0.61476 (15)	0.64179 (9)	0.0303 (4)
H13	0.0785	0.6664	0.6689	0.036*
C14	−0.0896 (3)	0.55131 (13)	0.75275 (9)	0.0261 (4)
C15	−0.0445 (3)	0.58425 (13)	0.81488 (8)	0.0254 (4)
H15	0.0808	0.5648	0.8382	0.030*
C16	−0.1772 (3)	0.64407 (13)	0.84292 (8)	0.0255 (4)
C17	−0.3626 (3)	0.67311 (13)	0.80926 (9)	0.0278 (4)
C18	−0.4093 (3)	0.64144 (14)	0.74781 (9)	0.0304 (4)
H18	−0.5351	0.6606	0.7247	0.037*
C19	−0.2734 (3)	0.58161 (14)	0.71962 (9)	0.0293 (4)
H19	−0.3067	0.5612	0.6772	0.035*
C20	0.0428 (3)	0.64921 (17)	0.93982 (9)	0.0369 (5)
H20A	0.0476	0.5753	0.9428	0.055*
H20B	0.0485	0.6782	0.9820	0.055*
H20C	0.1591	0.6734	0.9199	0.055*
C21	−0.6601 (3)	0.77604 (16)	0.80687 (10)	0.0388 (5)
H21A	−0.6192	0.8187	0.7733	0.058*
H21B	−0.7324	0.8172	0.8349	0.058*
H21C	−0.7499	0.7220	0.7885	0.058*

	U11	U22	U33	U12	U13	U23
Cl1	0.0525 (4)	0.0813 (5)	0.0412 (3)	0.0133 (3)	0.0173 (3)	0.0147 (3)
O1	0.0326 (8)	0.0484 (8)	0.0281 (7)	−0.0095 (7)	−0.0041 (6)	0.0043 (6)
O2	0.0226 (7)	0.0352 (7)	0.0529 (9)	−0.0019 (6)	0.0031 (6)	0.0124 (7)
O3	0.0356 (8)	0.0358 (7)	0.0283 (7)	0.0058 (6)	−0.0015 (6)	−0.0037 (6)
O4	0.0333 (8)	0.0410 (8)	0.0362 (8)	0.0113 (6)	0.0048 (6)	0.0003 (6)
N1	0.0243 (8)	0.0340 (9)	0.0255 (8)	−0.0049 (7)	0.0017 (7)	0.0040 (7)
C1	0.0235 (10)	0.0395 (11)	0.0283 (10)	−0.0039 (8)	0.0028 (8)	0.0010 (9)
C2	0.0310 (11)	0.0399 (11)	0.0325 (11)	−0.0102 (9)	0.0011 (9)	0.0024 (9)
C3	0.0363 (12)	0.0462 (12)	0.0270 (10)	−0.0058 (10)	0.0045 (9)	0.0025 (9)
C4	0.0324 (11)	0.0373 (11)	0.0309 (11)	−0.0074 (9)	0.0045 (9)	0.0065 (9)
C5	0.0241 (9)	0.0211 (9)	0.0346 (10)	0.0003 (7)	0.0028 (8)	−0.0010 (8)
C6	0.0238 (9)	0.0271 (9)	0.0313 (10)	−0.0006 (8)	−0.0001 (8)	−0.0017 (8)
C7	0.0236 (9)	0.0252 (9)	0.0285 (10)	−0.0032 (8)	−0.0027 (8)	−0.0029 (8)
C8	0.0228 (9)	0.0302 (10)	0.0279 (10)	0.0004 (8)	−0.0020 (8)	−0.0016 (8)
C9	0.0378 (12)	0.0332 (10)	0.0347 (11)	0.0031 (9)	0.0020 (9)	−0.0045 (9)
C10	0.0394 (12)	0.0484 (13)	0.0361 (12)	0.0060 (10)	0.0077 (10)	−0.0077 (10)
C11	0.0301 (11)	0.0539 (13)	0.0298 (11)	0.0056 (10)	0.0046 (9)	0.0057 (10)
C12	0.0290 (11)	0.0387 (11)	0.0360 (11)	0.0038 (9)	−0.0013 (9)	0.0073 (9)
C13	0.0279 (10)	0.0313 (10)	0.0299 (10)	0.0036 (8)	−0.0031 (8)	0.0015 (8)
C14	0.0251 (9)	0.0232 (9)	0.0291 (10)	−0.0019 (7)	−0.0003 (8)	0.0024 (8)
C15	0.0236 (9)	0.0229 (9)	0.0278 (10)	−0.0012 (7)	−0.0032 (8)	0.0029 (7)
C16	0.0270 (10)	0.0235 (9)	0.0253 (10)	−0.0024 (7)	0.0008 (8)	0.0025 (7)
C17	0.0250 (10)	0.0245 (9)	0.0343 (11)	−0.0001 (8)	0.0051 (8)	0.0042 (8)
C18	0.0224 (9)	0.0326 (10)	0.0345 (11)	0.0010 (8)	−0.0033 (8)	0.0043 (8)
C19	0.0281 (10)	0.0304 (10)	0.0279 (10)	−0.0015 (8)	−0.0024 (8)	−0.0010 (8)
C20	0.0337 (11)	0.0473 (12)	0.0275 (11)	0.0019 (10)	−0.0055 (9)	−0.0033 (9)
C21	0.0278 (10)	0.0437 (12)	0.0458 (13)	0.0082 (9)	0.0084 (9)	0.0084 (10)

Cl1—C11	1.739 (2)	C8—C9	1.390 (3)
O1—C2	1.424 (2)	C8—C13	1.395 (3)
O1—C3	1.426 (2)	C9—C10	1.388 (3)
O2—C5	1.230 (2)	C9—H9	0.9500
O3—C16	1.368 (2)	C10—C11	1.380 (3)
O3—C20	1.423 (2)	C10—H10	0.9500
O4—C17	1.378 (2)	C11—C12	1.373 (3)
O4—C21	1.417 (2)	C12—C13	1.390 (3)
N1—C5	1.351 (2)	C12—H12	0.9500
N1—C4	1.461 (2)	C13—H13	0.9500
N1—C1	1.464 (2)	C14—C19	1.390 (3)
C1—C2	1.505 (3)	C14—C15	1.400 (3)
C1—H1A	0.9900	C15—C16	1.376 (3)
C1—H1B	0.9900	C15—H15	0.9500
C2—H2A	0.9900	C16—C17	1.398 (3)
C2—H2B	0.9900	C17—C18	1.383 (3)
C3—C4	1.505 (3)	C18—C19	1.392 (3)
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C19—H19	0.9500
C4—H4A	0.9900	C20—H20A	0.9800
C4—H4B	0.9900	C20—H20B	0.9800
C5—C6	1.490 (3)	C20—H20C	0.9800
C6—C7	1.342 (3)	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—C14	1.487 (3)	C21—H21C	0.9800
C7—C8	1.487 (3)
C2—O1—C3	110.32 (15)	C8—C9—H9	119.5
C16—O3—C20	117.63 (15)	C11—C10—C9	119.3 (2)
C17—O4—C21	117.58 (15)	C11—C10—H10	120.3
C5—N1—C4	121.14 (16)	C9—C10—H10	120.3
C5—N1—C1	125.36 (16)	C12—C11—C10	121.2 (2)
C4—N1—C1	113.35 (15)	C12—C11—Cl1	119.04 (17)
N1—C1—C2	109.58 (15)	C10—C11—Cl1	119.71 (17)
N1—C1—H1A	109.8	C11—C12—C13	119.03 (19)
C2—C1—H1A	109.8	C11—C12—H12	120.5
N1—C1—H1B	109.8	C13—C12—H12	120.5
C2—C1—H1B	109.8	C12—C13—C8	121.15 (19)
H1A—C1—H1B	108.2	C12—C13—H13	119.4
O1—C2—C1	111.87 (16)	C8—C13—H13	119.4
O1—C2—H2A	109.2	C19—C14—C15	117.86 (17)
C1—C2—H2A	109.2	C19—C14—C7	122.03 (17)
O1—C2—H2B	109.2	C15—C14—C7	120.10 (17)
C1—C2—H2B	109.2	C16—C15—C14	121.60 (17)
H2A—C2—H2B	107.9	C16—C15—H15	119.2
O1—C3—C4	111.29 (16)	C14—C15—H15	119.2
O1—C3—H3A	109.4	O3—C16—C15	124.38 (17)
C4—C3—H3A	109.4	O3—C16—C17	115.68 (17)
O1—C3—H3B	109.4	C15—C16—C17	119.94 (17)
C4—C3—H3B	109.4	O4—C17—C18	125.23 (17)
H3A—C3—H3B	108.0	O4—C17—C16	115.56 (17)
N1—C4—C3	110.16 (16)	C18—C17—C16	119.21 (18)
N1—C4—H4A	109.6	C17—C18—C19	120.49 (18)
C3—C4—H4A	109.6	C17—C18—H18	119.8
N1—C4—H4B	109.6	C19—C18—H18	119.8
C3—C4—H4B	109.6	C14—C19—C18	120.89 (18)
H4A—C4—H4B	108.1	C14—C19—H19	119.6
O2—C5—N1	121.99 (18)	C18—C19—H19	119.6
O2—C5—C6	121.71 (17)	O3—C20—H20A	109.5
N1—C5—C6	116.24 (16)	O3—C20—H20B	109.5
C7—C6—C5	126.17 (17)	H20A—C20—H20B	109.5
C7—C6—H6	116.9	O3—C20—H20C	109.5
C5—C6—H6	116.9	H20A—C20—H20C	109.5
C6—C7—C14	122.97 (18)	H20B—C20—H20C	109.5
C6—C7—C8	118.35 (17)	O4—C21—H21A	109.5
C14—C7—C8	118.52 (16)	O4—C21—H21B	109.5
C9—C8—C13	118.25 (18)	H21A—C21—H21B	109.5
C9—C8—C7	121.42 (17)	O4—C21—H21C	109.5
C13—C8—C7	120.18 (17)	H21A—C21—H21C	109.5
C10—C9—C8	120.9 (2)	H21B—C21—H21C	109.5
C10—C9—H9	119.5
C5—N1—C1—C2	132.71 (19)	Cl1—C11—C12—C13	−179.22 (15)
C4—N1—C1—C2	−51.7 (2)	C11—C12—C13—C8	1.9 (3)
C3—O1—C2—C1	−60.0 (2)	C9—C8—C13—C12	−2.9 (3)
N1—C1—C2—O1	55.2 (2)	C7—C8—C13—C12	172.68 (17)
C2—O1—C3—C4	59.7 (2)	C6—C7—C14—C19	−139.6 (2)
C5—N1—C4—C3	−132.19 (19)	C8—C7—C14—C19	45.1 (2)
C1—N1—C4—C3	52.0 (2)	C6—C7—C14—C15	41.5 (3)
O1—C3—C4—N1	−55.3 (2)	C8—C7—C14—C15	−133.79 (18)
C4—N1—C5—O2	8.1 (3)	C19—C14—C15—C16	0.5 (3)
C1—N1—C5—O2	−176.63 (17)	C7—C14—C15—C16	179.42 (16)
C4—N1—C5—C6	−169.19 (17)	C20—O3—C16—C15	−2.2 (3)
C1—N1—C5—C6	6.1 (3)	C20—O3—C16—C17	178.19 (16)
O2—C5—C6—C7	50.0 (3)	C14—C15—C16—O3	−179.46 (17)
N1—C5—C6—C7	−132.7 (2)	C14—C15—C16—C17	0.2 (3)
C5—C6—C7—C14	9.2 (3)	C21—O4—C17—C18	−8.5 (3)
C5—C6—C7—C8	−175.53 (17)	C21—O4—C17—C16	171.23 (17)
C6—C7—C8—C9	37.0 (3)	O3—C16—C17—O4	−0.4 (2)
C14—C7—C8—C9	−147.52 (18)	C15—C16—C17—O4	179.97 (16)
C6—C7—C8—C13	−138.47 (19)	O3—C16—C17—C18	179.34 (16)
C14—C7—C8—C13	37.0 (2)	C15—C16—C17—C18	−0.3 (3)
C13—C8—C9—C10	1.6 (3)	O4—C17—C18—C19	179.47 (17)
C7—C8—C9—C10	−173.99 (18)	C16—C17—C18—C19	−0.2 (3)
C8—C9—C10—C11	0.8 (3)	C15—C14—C19—C18	−1.0 (3)
C9—C10—C11—C12	−1.8 (3)	C7—C14—C19—C18	−179.93 (17)
C9—C10—C11—Cl1	177.89 (16)	C17—C18—C19—C14	0.9 (3)
C10—C11—C12—C13	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.99	2.53	3.167 (2)	122
C13—H13···O2ii	0.95	2.38	3.166 (2)	140
C20—H20B···O1iii	0.98	2.64	3.010 (2)	103

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1BO2i	0.99	2.53	3.167(2)	122
C13H13O2ii	0.95	2.38	3.166(2)	140
C20H20BO1iii	0.98	2.64	3.010(2)	103

Symmetry codes: (i) ; (ii) ; (iii) .