Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Next article cross.png

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 9| September 2015| Page o654
https://doi.org/10.1107/S2056989015014735

Crystal structure of dimethomorph

CROSSMARK_Color_square_no_text.svg
Gihaeng Kang,a Jineun Kim,a* Eunjin Kwona and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by P. C. Healy, Griffith University, Australia (Received 2 August 2015; accepted 6 August 2015; online 12 August 2015)

In the title compound, C21H22ClNO4 [systematic name: (E)-3-(4-chloro­phen­yl)-3-(3,4-di­meth­oxy­phen­yl)-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 chloro­phenyl 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.

CCDC reference: 1417163

Similar articles

1. Related literature

For information on the fungicidal properties of the title compound, see: Xu et al. (2015[Xu, X., Liang, S., Meng, X., Zhang, M., Chen, Y., Zhao, D. & Li, Y. (2015). J. Chromatogr. B, 988, 182-186.]). For related crystal structures, see: Chai & Liu (2011[Chai, B. & Liu, C. (2011). Acta Cryst. E67, o1780.]); Lu & Shi (2011[Lu, B.-L. & Shi, M. (2011). Chem. Eur. J. 17, 9070-9075.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H22ClNO4

  • Mr = 387.84

  • Monoclinic, P 21 /c

  • 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

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.917, Tmax = 0.993

  • 18090 measured reflections

  • 4276 independent reflections

  • 3119 reflections with I > 2σ(I)

  • Rint = 0.047

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) x+1, y, z; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1417163

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015014735/hg5456sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014735/hg5456Isup2.hkl

checkCIF report


Comment top

Dimethomorph [systematic name: (E)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-(morpholin-4-yl)prop-2-en-1-one] is a morpholine fungicide that has been mainly applied on grapevines, apples, ginsengs, tomatoes, potatoes, cucumbers, Chinese cabbage and other crops. (Xu et al., 2015). The dihedral angles between the planes of the central chlorophenyl and the terminal benzene and mean plane [r.m.s. deviation = 0.2233] of morpholine rings are 71.74 (6) and 63.65 (7)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Chai & Liu, 2011; Lu & Shi, 2011).

In the crystal structure (Fig. 2), C—H···O hydrogen bonds (Table 1) and weak intermolecular C11—Cl1···Cg1iv (Cg1 is the centroid of the C8—C13 ring) interaction with a chlorophenyl ring are present, resulting in a three-dimensional network [for symmetry code: (iv), -x, -y + 1, -z + 1].

Related literature top

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

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3OH gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for Csp2—H and aromatic C—H.

Structure description top

Dimethomorph [systematic name: (E)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-(morpholin-4-yl)prop-2-en-1-one] is a morpholine fungicide that has been mainly applied on grapevines, apples, ginsengs, tomatoes, potatoes, cucumbers, Chinese cabbage and other crops. (Xu et al., 2015). The dihedral angles between the planes of the central chlorophenyl and the terminal benzene and mean plane [r.m.s. deviation = 0.2233] of morpholine rings are 71.74 (6) and 63.65 (7)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Chai & Liu, 2011; Lu & Shi, 2011).

In the crystal structure (Fig. 2), C—H···O hydrogen bonds (Table 1) and weak intermolecular C11—Cl1···Cg1iv (Cg1 is the centroid of the C8—C13 ring) interaction with a chlorophenyl ring are present, resulting in a three-dimensional network [for symmetry code: (iv), -x, -y + 1, -z + 1].

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

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).

Figures top
[Figure 1] Fig. 1. 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.
[Figure 2] Fig. 2. Crystal packing viewed along the a axis. The intermolecular interactions are shown as dashed lines.
(E)-3-(4-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-(morpholin-4-yl)prop-2-en-1-one top
Crystal data top
C21H22ClNO4F(000) = 816
Mr = 387.84Dx = 1.380 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.6238 (2) ÅCell parameters from 3670 reflections
b = 13.2232 (4) Åθ = 2.5–24.0°
c = 21.4810 (7) ŵ = 0.23 mm−1
β = 97.1674 (19)°T = 173 K
V = 1866.77 (10) Å3Needle, colourless
Z = 40.38 × 0.06 × 0.03 mm
Data collection top
Bruker APEXII CCD
diffractometer		3119 reflections with I > 2σ(I)
φ and ω scansRint = 0.047
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 27.5°, θmin = 1.8°
Tmin = 0.917, Tmax = 0.993h = −8→8
18090 measured reflectionsk = −14→17
4276 independent reflectionsl = −27→27
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.059P)2 + 0.6606P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4276 reflectionsΔρmax = 0.27 e Å−3
246 parametersΔρmin = −0.53 e Å−3
Crystal data top
C21H22ClNO4V = 1866.77 (10) Å3
Mr = 387.84Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.6238 (2) ŵ = 0.23 mm−1
b = 13.2232 (4) ÅT = 173 K
c = 21.4810 (7) Å0.38 × 0.06 × 0.03 mm
β = 97.1674 (19)°
Data collection top
Bruker APEXII CCD
diffractometer		4276 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		3119 reflections with I > 2σ(I)
Tmin = 0.917, Tmax = 0.993Rint = 0.047
18090 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å−3
4276 reflectionsΔρmin = −0.53 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.31366 (10)0.59912 (5)0.47448 (3)0.0574 (2)
O10.5956 (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)
N10.2962 (2)0.35718 (12)0.85873 (7)0.0281 (4)
C10.5023 (3)0.38939 (15)0.84994 (9)0.0305 (4)
H1A0.49690.43470.81310.037*
H1B0.58550.32960.84210.037*
C20.5976 (3)0.44402 (16)0.90772 (9)0.0347 (5)
H2A0.73990.46170.90270.042*
H2B0.52260.50780.91250.042*
C30.3918 (3)0.35949 (17)0.97178 (9)0.0364 (5)
H3A0.31500.42240.97720.044*
H3B0.39280.31871.01040.044*
C40.2872 (3)0.30099 (16)0.91686 (9)0.0335 (5)
H4A0.35420.23450.91420.040*
H4B0.14340.28900.92290.040*
C50.1286 (3)0.37008 (13)0.81674 (9)0.0267 (4)
C60.1627 (3)0.41177 (14)0.75448 (9)0.0277 (4)
H60.26830.38190.73460.033*
C70.0584 (3)0.48755 (13)0.72382 (9)0.0263 (4)
C80.1046 (3)0.51370 (14)0.65975 (9)0.0274 (4)
C90.1513 (3)0.43952 (16)0.61797 (9)0.0354 (5)
H90.14120.37020.62890.043*
C100.2124 (3)0.46527 (17)0.56054 (10)0.0411 (5)
H100.24240.41400.53210.049*
C110.2291 (3)0.56604 (18)0.54519 (10)0.0378 (5)
C120.1811 (3)0.64122 (16)0.58492 (10)0.0350 (5)
H120.19230.71030.57370.042*
C130.1159 (3)0.61476 (15)0.64179 (9)0.0303 (4)
H130.07850.66640.66890.036*
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)
H150.08080.56480.83820.030*
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)
H18−0.53510.66060.72470.037*
C19−0.2734 (3)0.58161 (14)0.71962 (9)0.0293 (4)
H19−0.30670.56120.67720.035*
C200.0428 (3)0.64921 (17)0.93982 (9)0.0369 (5)
H20A0.04760.57530.94280.055*
H20B0.04850.67820.98200.055*
H20C0.15910.67340.91990.055*
C21−0.6601 (3)0.77604 (16)0.80687 (10)0.0388 (5)
H21A−0.61920.81870.77330.058*
H21B−0.73240.81720.83490.058*
H21C−0.74990.72200.78850.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0525 (4)0.0813 (5)0.0412 (3)0.0133 (3)0.0173 (3)0.0147 (3)
O10.0326 (8)0.0484 (8)0.0281 (7)−0.0095 (7)−0.0041 (6)0.0043 (6)
O20.0226 (7)0.0352 (7)0.0529 (9)−0.0019 (6)0.0031 (6)0.0124 (7)
O30.0356 (8)0.0358 (7)0.0283 (7)0.0058 (6)−0.0015 (6)−0.0037 (6)
O40.0333 (8)0.0410 (8)0.0362 (8)0.0113 (6)0.0048 (6)0.0003 (6)
N10.0243 (8)0.0340 (9)0.0255 (8)−0.0049 (7)0.0017 (7)0.0040 (7)
C10.0235 (10)0.0395 (11)0.0283 (10)−0.0039 (8)0.0028 (8)0.0010 (9)
C20.0310 (11)0.0399 (11)0.0325 (11)−0.0102 (9)0.0011 (9)0.0024 (9)
C30.0363 (12)0.0462 (12)0.0270 (10)−0.0058 (10)0.0045 (9)0.0025 (9)
C40.0324 (11)0.0373 (11)0.0309 (11)−0.0074 (9)0.0045 (9)0.0065 (9)
C50.0241 (9)0.0211 (9)0.0346 (10)0.0003 (7)0.0028 (8)−0.0010 (8)
C60.0238 (9)0.0271 (9)0.0313 (10)−0.0006 (8)−0.0001 (8)−0.0017 (8)
C70.0236 (9)0.0252 (9)0.0285 (10)−0.0032 (8)−0.0027 (8)−0.0029 (8)
C80.0228 (9)0.0302 (10)0.0279 (10)0.0004 (8)−0.0020 (8)−0.0016 (8)
C90.0378 (12)0.0332 (10)0.0347 (11)0.0031 (9)0.0020 (9)−0.0045 (9)
C100.0394 (12)0.0484 (13)0.0361 (12)0.0060 (10)0.0077 (10)−0.0077 (10)
C110.0301 (11)0.0539 (13)0.0298 (11)0.0056 (10)0.0046 (9)0.0057 (10)
C120.0290 (11)0.0387 (11)0.0360 (11)0.0038 (9)−0.0013 (9)0.0073 (9)
C130.0279 (10)0.0313 (10)0.0299 (10)0.0036 (8)−0.0031 (8)0.0015 (8)
C140.0251 (9)0.0232 (9)0.0291 (10)−0.0019 (7)−0.0003 (8)0.0024 (8)
C150.0236 (9)0.0229 (9)0.0278 (10)−0.0012 (7)−0.0032 (8)0.0029 (7)
C160.0270 (10)0.0235 (9)0.0253 (10)−0.0024 (7)0.0008 (8)0.0025 (7)
C170.0250 (10)0.0245 (9)0.0343 (11)−0.0001 (8)0.0051 (8)0.0042 (8)
C180.0224 (9)0.0326 (10)0.0345 (11)0.0010 (8)−0.0033 (8)0.0043 (8)
C190.0281 (10)0.0304 (10)0.0279 (10)−0.0015 (8)−0.0024 (8)−0.0010 (8)
C200.0337 (11)0.0473 (12)0.0275 (11)0.0019 (10)−0.0055 (9)−0.0033 (9)
C210.0278 (10)0.0437 (12)0.0458 (13)0.0082 (9)0.0084 (9)0.0084 (10)
Geometric parameters (Å, º) top
Cl1—C111.739 (2)C8—C91.390 (3)
O1—C21.424 (2)C8—C131.395 (3)
O1—C31.426 (2)C9—C101.388 (3)
O2—C51.230 (2)C9—H90.9500
O3—C161.368 (2)C10—C111.380 (3)
O3—C201.423 (2)C10—H100.9500
O4—C171.378 (2)C11—C121.373 (3)
O4—C211.417 (2)C12—C131.390 (3)
N1—C51.351 (2)C12—H120.9500
N1—C41.461 (2)C13—H130.9500
N1—C11.464 (2)C14—C191.390 (3)
C1—C21.505 (3)C14—C151.400 (3)
C1—H1A0.9900C15—C161.376 (3)
C1—H1B0.9900C15—H150.9500
C2—H2A0.9900C16—C171.398 (3)
C2—H2B0.9900C17—C181.383 (3)
C3—C41.505 (3)C18—C191.392 (3)
C3—H3A0.9900C18—H180.9500
C3—H3B0.9900C19—H190.9500
C4—H4A0.9900C20—H20A0.9800
C4—H4B0.9900C20—H20B0.9800
C5—C61.490 (3)C20—H20C0.9800
C6—C71.342 (3)C21—H21A0.9800
C6—H60.9500C21—H21B0.9800
C7—C141.487 (3)C21—H21C0.9800
C7—C81.487 (3)
C2—O1—C3110.32 (15)C8—C9—H9119.5
C16—O3—C20117.63 (15)C11—C10—C9119.3 (2)
C17—O4—C21117.58 (15)C11—C10—H10120.3
C5—N1—C4121.14 (16)C9—C10—H10120.3
C5—N1—C1125.36 (16)C12—C11—C10121.2 (2)
C4—N1—C1113.35 (15)C12—C11—Cl1119.04 (17)
N1—C1—C2109.58 (15)C10—C11—Cl1119.71 (17)
N1—C1—H1A109.8C11—C12—C13119.03 (19)
C2—C1—H1A109.8C11—C12—H12120.5
N1—C1—H1B109.8C13—C12—H12120.5
C2—C1—H1B109.8C12—C13—C8121.15 (19)
H1A—C1—H1B108.2C12—C13—H13119.4
O1—C2—C1111.87 (16)C8—C13—H13119.4
O1—C2—H2A109.2C19—C14—C15117.86 (17)
C1—C2—H2A109.2C19—C14—C7122.03 (17)
O1—C2—H2B109.2C15—C14—C7120.10 (17)
C1—C2—H2B109.2C16—C15—C14121.60 (17)
H2A—C2—H2B107.9C16—C15—H15119.2
O1—C3—C4111.29 (16)C14—C15—H15119.2
O1—C3—H3A109.4O3—C16—C15124.38 (17)
C4—C3—H3A109.4O3—C16—C17115.68 (17)
O1—C3—H3B109.4C15—C16—C17119.94 (17)
C4—C3—H3B109.4O4—C17—C18125.23 (17)
H3A—C3—H3B108.0O4—C17—C16115.56 (17)
N1—C4—C3110.16 (16)C18—C17—C16119.21 (18)
N1—C4—H4A109.6C17—C18—C19120.49 (18)
C3—C4—H4A109.6C17—C18—H18119.8
N1—C4—H4B109.6C19—C18—H18119.8
C3—C4—H4B109.6C14—C19—C18120.89 (18)
H4A—C4—H4B108.1C14—C19—H19119.6
O2—C5—N1121.99 (18)C18—C19—H19119.6
O2—C5—C6121.71 (17)O3—C20—H20A109.5
N1—C5—C6116.24 (16)O3—C20—H20B109.5
C7—C6—C5126.17 (17)H20A—C20—H20B109.5
C7—C6—H6116.9O3—C20—H20C109.5
C5—C6—H6116.9H20A—C20—H20C109.5
C6—C7—C14122.97 (18)H20B—C20—H20C109.5
C6—C7—C8118.35 (17)O4—C21—H21A109.5
C14—C7—C8118.52 (16)O4—C21—H21B109.5
C9—C8—C13118.25 (18)H21A—C21—H21B109.5
C9—C8—C7121.42 (17)O4—C21—H21C109.5
C13—C8—C7120.18 (17)H21A—C21—H21C109.5
C10—C9—C8120.9 (2)H21B—C21—H21C109.5
C10—C9—H9119.5
C5—N1—C1—C2132.71 (19)Cl1—C11—C12—C13−179.22 (15)
C4—N1—C1—C2−51.7 (2)C11—C12—C13—C81.9 (3)
C3—O1—C2—C1−60.0 (2)C9—C8—C13—C12−2.9 (3)
N1—C1—C2—O155.2 (2)C7—C8—C13—C12172.68 (17)
C2—O1—C3—C459.7 (2)C6—C7—C14—C19−139.6 (2)
C5—N1—C4—C3−132.19 (19)C8—C7—C14—C1945.1 (2)
C1—N1—C4—C352.0 (2)C6—C7—C14—C1541.5 (3)
O1—C3—C4—N1−55.3 (2)C8—C7—C14—C15−133.79 (18)
C4—N1—C5—O28.1 (3)C19—C14—C15—C160.5 (3)
C1—N1—C5—O2−176.63 (17)C7—C14—C15—C16179.42 (16)
C4—N1—C5—C6−169.19 (17)C20—O3—C16—C15−2.2 (3)
C1—N1—C5—C66.1 (3)C20—O3—C16—C17178.19 (16)
O2—C5—C6—C750.0 (3)C14—C15—C16—O3−179.46 (17)
N1—C5—C6—C7−132.7 (2)C14—C15—C16—C170.2 (3)
C5—C6—C7—C149.2 (3)C21—O4—C17—C18−8.5 (3)
C5—C6—C7—C8−175.53 (17)C21—O4—C17—C16171.23 (17)
C6—C7—C8—C937.0 (3)O3—C16—C17—O4−0.4 (2)
C14—C7—C8—C9−147.52 (18)C15—C16—C17—O4179.97 (16)
C6—C7—C8—C13−138.47 (19)O3—C16—C17—C18179.34 (16)
C14—C7—C8—C1337.0 (2)C15—C16—C17—C18−0.3 (3)
C13—C8—C9—C101.6 (3)O4—C17—C18—C19179.47 (17)
C7—C8—C9—C10−173.99 (18)C16—C17—C18—C19−0.2 (3)
C8—C9—C10—C110.8 (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—Cl1177.89 (16)C17—C18—C19—C140.9 (3)
C10—C11—C12—C130.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O2i0.992.533.167 (2)122
C13—H13···O2ii0.952.383.166 (2)140
C20—H20B···O1iii0.982.643.010 (2)103
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O2i0.992.533.167 (2)121.8
C13—H13···O2ii0.952.383.166 (2)139.9
C20—H20B···O1iii0.982.643.010 (2)102.8
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

References

First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChai, B. & Liu, C. (2011). Acta Cryst. E67, o1780.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLu, B.-L. & Shi, M. (2011). Chem. Eur. J. 17, 9070–9075.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationXu, X., Liang, S., Meng, X., Zhang, M., Chen, Y., Zhao, D. & Li, Y. (2015). J. Chromatogr. B, 988, 182–186.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 9| September 2015| Page o654
https://doi.org/10.1107/S2056989015014735
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS