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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 10| October 2015| Pages o727-o728
doi:10.1107/S2056989015016643

Crystal structure of mandipropamid

CROSSMARK_Color_square_no_text.svg
Hyunjin Park,a Jineun Kim,a* Gihaeng Kanga and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 31 August 2015; accepted 7 September 2015; online 12 September 2015)

In the title compound, C23H22ClNO4 (systematic name: (RS)-2-(4-chloro­phen­yl)-N-{2-[3-meth­oxy-4-(prop-2-yn-1-yl­oxy)phen­yl]eth­yl}-2-(prop-2-yn­yloxy)acetamide), an amide fungicide, the dihedral angle between the chloro­benzene and benzene rings is 65.36 (6)°. In the crystal, N—H⋯O hydrogen bonds lead to zigzag supra­molecular chains along the c axis (glide symmetry). These are connected into layers by C—H⋯O and C—H⋯π inter­actions; the layers stack along the a axis with no specific inter­molecular inter­actions between them.

CCDC reference: 1422569

1. Related literature

For information on the fungicidal properties of the title compound, see: Zhang et al. (2014[Zhang, H., Wang, X., Wang, X., Qian, M., Xu, M., Xu, H., Qi, P., Wang, Q. & Zhuang, S. (2014). J. Sep. Sci. 37, 211-218.]). For a related crystal structure, see: Davis & Healy (2008[Davis, R. A. & Healy, P. C. (2008). Acta Cryst. E64, o1057.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C23H22ClNO4

  • Mr = 411.86

  • Monoclinic, P 21 /c

  • a = 26.3733 (17) Å

  • b = 9.4740 (6) Å

  • c = 8.4882 (5) Å

  • β = 91.013 (3)°

  • V = 2120.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 173 K

  • 0.22 × 0.15 × 0.10 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 = 0.722, Tmax = 0.746

  • 36727 measured reflections

  • 4885 independent reflections

  • 3686 reflections with I > 2σ(I)

  • Rint = 0.039

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.131

  • S = 1.04

  • 4885 reflections

  • 263 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14–C19 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.88 2.04 2.850 (2) 152
C10—H10⋯O2ii 0.95 2.35 3.218 (3) 152
C12—H12A⋯O1iii 0.99 2.53 3.232 (3) 128
C20—H20C⋯Cg2iv 0.98 2.84 3.709 (3) 148
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z-{\script{1\over 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: 1422569

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016643/tk5382sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016643/tk5382Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016643/tk5382Isup3.cml

checkCIF report


Comment top

Mandipropamid [systematic name: (RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide] is a the amide fungicide that is used on potato, tomato, pepper, grape, watermelon, and litchi. (Zhang et al., 2014). The dihedral angle between the chlorobenzene and the benzene rings is 65.36 (6)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Davis & Healy, 2008).

In the crystal structure (Fig. 2), N–H···O and C–H···O hydrogen bonds and weak C–H···π interactions (Table 1) link adjacent molecules.

Related literature top

For information on the fungicidal properties of the title compound, see: Zhang et al. (2014). For a related crystal structure, see: Davis & Healy (2008).

Experimental top

The title compound was purchased from Dr. Ehrenstorfer GmbH. Slow evaporation of its solution in CH3CN gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(N—H) = 0.88 Å, Uiso = 1.2Ueq(C) for N—H, and d(C—H) = 0.95–1.00 Å, Uiso = 1.2–1.5Ueq(C) for C—H. Owing to poor agreement, one reflection, i.e. ( 1 0 0), was omitted from the final cycles of refinement.

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 molecular structure 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 b axis. The hydrogen bonds are shown as dashed lines.
(RS)-2-(4-Chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-ynyloxy)acetamide top
Crystal data top
C23H22ClNO4F(000) = 864
Mr = 411.86Dx = 1.290 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 26.3733 (17) ÅCell parameters from 9957 reflections
b = 9.4740 (6) Åθ = 2.3–26.3°
c = 8.4882 (5) ŵ = 0.21 mm−1
β = 91.013 (3)°T = 173 K
V = 2120.5 (2) Å3Plate, colourless
Z = 40.22 × 0.15 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer		3686 reflections with I > 2σ(I)
φ and ω scansRint = 0.039
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 27.6°, θmin = 2.3°
Tmin = 0.722, Tmax = 0.746h = −33→34
36727 measured reflectionsk = −12→12
4885 independent reflectionsl = −11→10
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0444P)2 + 1.677P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4885 reflectionsΔρmax = 0.82 e Å−3
263 parametersΔρmin = −0.29 e Å−3
Crystal data top
C23H22ClNO4V = 2120.5 (2) Å3
Mr = 411.86Z = 4
Monoclinic, P21/cMo Kα radiation
a = 26.3733 (17) ŵ = 0.21 mm−1
b = 9.4740 (6) ÅT = 173 K
c = 8.4882 (5) Å0.22 × 0.15 × 0.10 mm
β = 91.013 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		4885 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		3686 reflections with I > 2σ(I)
Tmin = 0.722, Tmax = 0.746Rint = 0.039
36727 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.131H-atom parameters constrained
S = 1.04Δρmax = 0.82 e Å−3
4885 reflectionsΔρmin = −0.29 e Å−3
263 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
Cl10.45595 (2)0.22978 (7)0.12537 (9)0.0543 (2)
O10.67498 (6)0.42193 (16)−0.19373 (17)0.0376 (4)
O20.70934 (5)0.38856 (15)0.20630 (16)0.0332 (3)
O30.86165 (6)−0.36494 (16)0.1328 (2)0.0442 (4)
O40.93566 (5)−0.26941 (15)0.30322 (18)0.0383 (4)
N10.72949 (6)0.25526 (19)−0.0044 (2)0.0341 (4)
H1N0.72390.2407−0.10560.041*
C10.51676 (8)0.2878 (2)0.0816 (3)0.0355 (5)
C20.53176 (8)0.4194 (2)0.1302 (3)0.0375 (5)
H20.50940.47750.18830.045*
C30.57995 (8)0.4671 (2)0.0936 (2)0.0341 (5)
H30.59080.55760.12860.041*
C40.61212 (7)0.3842 (2)0.0069 (2)0.0298 (4)
C50.59606 (8)0.2516 (2)−0.0420 (3)0.0375 (5)
H50.61790.1942−0.10250.045*
C60.54833 (9)0.2019 (2)−0.0035 (3)0.0404 (5)
H60.53760.1103−0.03520.048*
C70.66491 (7)0.4385 (2)−0.0328 (2)0.0315 (4)
H70.66720.5409−0.00510.038*
C80.64981 (9)0.5251 (2)−0.2903 (3)0.0417 (5)
H8A0.61300.5220−0.27000.050*
H8B0.65470.5010−0.40250.050*
C90.66839 (9)0.6681 (3)−0.2614 (3)0.0446 (6)
C100.68291 (11)0.7840 (3)−0.2365 (3)0.0575 (7)
H100.69460.8773−0.21640.069*
C110.70398 (7)0.3566 (2)0.0662 (2)0.0291 (4)
C120.76667 (8)0.1662 (3)0.0785 (3)0.0380 (5)
H12A0.74920.08290.12220.046*
H12B0.78170.22000.16780.046*
C130.80847 (8)0.1170 (3)−0.0268 (3)0.0387 (5)
H13A0.79360.0687−0.12020.046*
H13B0.82800.1994−0.06390.046*
C140.84327 (8)0.0174 (2)0.0610 (2)0.0346 (5)
C150.83530 (8)−0.1280 (2)0.0534 (3)0.0355 (5)
H150.8081−0.1637−0.00960.043*
C160.86616 (8)−0.2208 (2)0.1356 (3)0.0343 (5)
C170.90637 (7)−0.1685 (2)0.2301 (2)0.0329 (5)
C180.91396 (8)−0.0250 (2)0.2401 (3)0.0376 (5)
H180.94070.01130.30460.045*
C190.88242 (8)0.0672 (2)0.1556 (3)0.0389 (5)
H190.88800.16610.16330.047*
C200.81997 (9)−0.4224 (3)0.0456 (3)0.0503 (6)
H20A0.7882−0.38640.08810.075*
H20B0.8206−0.52560.05380.075*
H20C0.8225−0.3948−0.06530.075*
C210.97493 (9)−0.2226 (3)0.4095 (3)0.0428 (5)
H21A0.9884−0.30490.46870.051*
H21B0.9603−0.15630.48640.051*
C221.01689 (8)−0.1525 (2)0.3292 (3)0.0417 (5)
C231.05017 (10)−0.0922 (3)0.2672 (4)0.0542 (7)
H231.0770−0.04350.21730.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0349 (3)0.0530 (4)0.0753 (5)−0.0051 (3)0.0082 (3)0.0229 (3)
O10.0426 (9)0.0383 (8)0.0318 (8)0.0099 (7)0.0019 (6)0.0045 (6)
O20.0363 (8)0.0359 (8)0.0272 (8)0.0032 (6)−0.0033 (6)−0.0002 (6)
O30.0406 (9)0.0346 (8)0.0572 (10)−0.0052 (7)−0.0040 (8)−0.0044 (7)
O40.0323 (8)0.0362 (8)0.0462 (9)0.0008 (6)−0.0047 (7)0.0013 (7)
N10.0321 (9)0.0464 (10)0.0238 (9)0.0094 (8)−0.0022 (7)0.0002 (8)
C10.0289 (10)0.0399 (12)0.0376 (12)−0.0010 (9)−0.0011 (9)0.0130 (10)
C20.0335 (11)0.0385 (12)0.0406 (12)0.0072 (9)0.0060 (9)0.0049 (10)
C30.0329 (11)0.0322 (11)0.0370 (12)0.0015 (9)−0.0007 (9)0.0025 (9)
C40.0278 (10)0.0342 (10)0.0272 (10)0.0023 (8)−0.0040 (8)0.0065 (8)
C50.0370 (12)0.0410 (12)0.0347 (12)0.0057 (9)0.0025 (9)−0.0018 (9)
C60.0408 (12)0.0361 (12)0.0440 (13)−0.0038 (10)−0.0043 (10)0.0021 (10)
C70.0285 (10)0.0390 (11)0.0270 (10)0.0053 (8)−0.0022 (8)−0.0002 (9)
C80.0417 (12)0.0439 (13)0.0394 (13)0.0066 (10)−0.0042 (10)0.0133 (10)
C90.0429 (13)0.0469 (14)0.0439 (14)0.0045 (11)−0.0002 (10)0.0175 (11)
C100.0650 (18)0.0500 (16)0.0574 (17)−0.0014 (13)−0.0046 (14)0.0125 (13)
C110.0238 (9)0.0344 (11)0.0290 (11)−0.0015 (8)0.0015 (8)0.0046 (8)
C120.0341 (11)0.0478 (13)0.0321 (12)0.0116 (10)0.0027 (9)0.0022 (10)
C130.0334 (11)0.0467 (13)0.0362 (12)0.0098 (10)0.0053 (9)0.0029 (10)
C140.0282 (10)0.0419 (12)0.0339 (11)0.0056 (9)0.0063 (8)−0.0003 (9)
C150.0260 (10)0.0448 (12)0.0355 (12)0.0007 (9)0.0004 (9)−0.0061 (10)
C160.0300 (10)0.0342 (11)0.0389 (12)−0.0003 (9)0.0049 (9)−0.0039 (9)
C170.0262 (10)0.0369 (11)0.0356 (11)0.0040 (8)0.0036 (8)−0.0006 (9)
C180.0273 (10)0.0384 (11)0.0471 (13)−0.0005 (9)−0.0014 (9)−0.0071 (10)
C190.0295 (11)0.0331 (11)0.0541 (14)0.0025 (9)0.0034 (10)−0.0022 (10)
C200.0419 (13)0.0477 (14)0.0611 (16)−0.0150 (11)0.0014 (12)−0.0080 (12)
C210.0380 (12)0.0478 (13)0.0426 (13)0.0008 (10)−0.0064 (10)0.0044 (11)
C220.0317 (11)0.0387 (12)0.0542 (14)0.0063 (10)−0.0086 (10)0.0004 (11)
C230.0346 (13)0.0445 (14)0.083 (2)0.0032 (11)−0.0008 (13)0.0063 (14)
Geometric parameters (Å, º) top
Cl1—C11.742 (2)C8—H8B0.9900
O1—C71.405 (2)C9—C101.181 (4)
O1—C81.432 (2)C10—H100.9500
O2—C111.232 (2)C12—C131.506 (3)
O3—C161.371 (3)C12—H12A0.9900
O3—C201.423 (3)C12—H12B0.9900
O4—C171.371 (2)C13—C141.505 (3)
O4—C211.432 (3)C13—H13A0.9900
N1—C111.323 (3)C13—H13B0.9900
N1—C121.464 (3)C14—C191.380 (3)
N1—H1N0.8800C14—C151.394 (3)
C1—C21.369 (3)C15—C161.379 (3)
C1—C61.378 (3)C15—H150.9500
C2—C31.389 (3)C16—C171.409 (3)
C2—H20.9500C17—C181.376 (3)
C3—C41.379 (3)C18—C191.396 (3)
C3—H30.9500C18—H180.9500
C4—C51.386 (3)C19—H190.9500
C4—C71.528 (3)C20—H20A0.9800
C5—C61.388 (3)C20—H20B0.9800
C5—H50.9500C20—H20C0.9800
C6—H60.9500C21—C221.469 (3)
C7—C111.529 (3)C21—H21A0.9900
C7—H71.0000C21—H21B0.9900
C8—C91.460 (4)C22—C231.179 (3)
C8—H8A0.9900C23—H230.9500
C7—O1—C8112.75 (16)C13—C12—H12A109.1
C16—O3—C20117.13 (18)N1—C12—H12B109.1
C17—O4—C21117.70 (17)C13—C12—H12B109.1
C11—N1—C12122.83 (17)H12A—C12—H12B107.8
C11—N1—H1N118.6C14—C13—C12110.27 (18)
C12—N1—H1N118.6C14—C13—H13A109.6
C2—C1—C6121.4 (2)C12—C13—H13A109.6
C2—C1—Cl1119.05 (17)C14—C13—H13B109.6
C6—C1—Cl1119.50 (18)C12—C13—H13B109.6
C1—C2—C3119.3 (2)H13A—C13—H13B108.1
C1—C2—H2120.3C19—C14—C15118.4 (2)
C3—C2—H2120.3C19—C14—C13121.1 (2)
C4—C3—C2120.5 (2)C15—C14—C13120.4 (2)
C4—C3—H3119.7C16—C15—C14121.3 (2)
C2—C3—H3119.7C16—C15—H15119.4
C3—C4—C5119.24 (19)C14—C15—H15119.4
C3—C4—C7119.81 (19)O3—C16—C15125.2 (2)
C5—C4—C7120.94 (19)O3—C16—C17115.09 (19)
C4—C5—C6120.7 (2)C15—C16—C17119.7 (2)
C4—C5—H5119.7O4—C17—C18125.51 (19)
C6—C5—H5119.7O4—C17—C16115.16 (18)
C1—C6—C5118.8 (2)C18—C17—C16119.3 (2)
C1—C6—H6120.6C17—C18—C19120.1 (2)
C5—C6—H6120.6C17—C18—H18119.9
O1—C7—C4111.42 (16)C19—C18—H18119.9
O1—C7—C11109.91 (16)C14—C19—C18121.2 (2)
C4—C7—C11108.39 (16)C14—C19—H19119.4
O1—C7—H7109.0C18—C19—H19119.4
C4—C7—H7109.0O3—C20—H20A109.5
C11—C7—H7109.0O3—C20—H20B109.5
O1—C8—C9112.75 (19)H20A—C20—H20B109.5
O1—C8—H8A109.0O3—C20—H20C109.5
C9—C8—H8A109.0H20A—C20—H20C109.5
O1—C8—H8B109.0H20B—C20—H20C109.5
C9—C8—H8B109.0O4—C21—C22112.97 (19)
H8A—C8—H8B107.8O4—C21—H21A109.0
C10—C9—C8179.0 (3)C22—C21—H21A109.0
C9—C10—H10180.0O4—C21—H21B109.0
O2—C11—N1124.40 (18)C22—C21—H21B109.0
O2—C11—C7118.06 (18)H21A—C21—H21B107.8
N1—C11—C7117.53 (17)C23—C22—C21177.8 (3)
N1—C12—C13112.59 (17)C22—C23—H23180.0
N1—C12—H12A109.1
C6—C1—C2—C3−0.3 (3)C11—N1—C12—C13−149.7 (2)
Cl1—C1—C2—C3−179.05 (17)N1—C12—C13—C14−175.73 (19)
C1—C2—C3—C41.2 (3)C12—C13—C14—C19−84.1 (3)
C2—C3—C4—C5−0.7 (3)C12—C13—C14—C1593.3 (3)
C2—C3—C4—C7179.77 (19)C19—C14—C15—C16−1.2 (3)
C3—C4—C5—C6−0.5 (3)C13—C14—C15—C16−178.71 (19)
C7—C4—C5—C6178.97 (19)C20—O3—C16—C15−3.9 (3)
C2—C1—C6—C5−0.9 (3)C20—O3—C16—C17176.77 (19)
Cl1—C1—C6—C5177.82 (17)C14—C15—C16—O3−178.8 (2)
C4—C5—C6—C11.3 (3)C14—C15—C16—C170.5 (3)
C8—O1—C7—C476.5 (2)C21—O4—C17—C185.6 (3)
C8—O1—C7—C11−163.30 (17)C21—O4—C17—C16−175.78 (18)
C3—C4—C7—O1−130.98 (19)O3—C16—C17—O41.2 (3)
C5—C4—C7—O149.5 (2)C15—C16—C17—O4−178.20 (18)
C3—C4—C7—C11108.0 (2)O3—C16—C17—C18179.9 (2)
C5—C4—C7—C11−71.5 (2)C15—C16—C17—C180.5 (3)
C7—O1—C8—C965.9 (2)O4—C17—C18—C19177.8 (2)
C12—N1—C11—O21.5 (3)C16—C17—C18—C19−0.8 (3)
C12—N1—C11—C7−177.93 (19)C15—C14—C19—C181.0 (3)
O1—C7—C11—O2161.04 (17)C13—C14—C19—C18178.4 (2)
C4—C7—C11—O2−77.0 (2)C17—C18—C19—C140.0 (3)
O1—C7—C11—N1−19.5 (3)C17—O4—C21—C22−69.6 (3)
C4—C7—C11—N1102.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C14–C19 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.882.042.850 (2)152
C10—H10···O2ii0.952.353.218 (3)152
C12—H12A···O1iii0.992.533.232 (3)128
C20—H20C···Cg2iv0.982.843.709 (3)148
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y−1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C14–C19 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.882.042.850 (2)152
C10—H10···O2ii0.952.353.218 (3)152
C12—H12A···O1iii0.992.533.232 (3)128
C20—H20C···Cg2iv0.982.843.709 (3)148
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y−1/2, z−1/2.
 

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 (grnat No. 2014R1A1A4A01009105).

References

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 First citationDavis, R. A. & Healy, P. C. (2008). Acta Cryst. E64, o1057.  Web of Science CSD CrossRef IUCr Journals 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 citationZhang, H., Wang, X., Wang, X., Qian, M., Xu, M., Xu, H., Qi, P., Wang, Q. & Zhuang, S. (2014). J. Sep. Sci. 37, 211–218.  CrossRef CAS PubMed Google Scholar

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ISSN: 2056-9890
Volume 71| Part 10| October 2015| Pages o727-o728
doi:10.1107/S2056989015016643
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