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ISSN: 2056-9890

Crystal structure of nuarimol

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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 July 2015; accepted 14 July 2015; online 22 July 2015)

The title compound [systematic name: (RS)-(2-chloro­phen­yl)(4-fluoro­phen­yl)(pyrimidin-5-yl)methanol], C17H12ClFN2O, is a pyrimidine fungicide. The asymmetric unit comprises two independent mol­ecules, A and B, in which the dihedral angles between the plane of the pyrimidine ring and those of the chloro­phenyl and fluoro­phenyl rings are 71.10 (6) and 70.04 (5)° in mol­ecule A, and 73.24 (5) and 89.30 (5)° in mol­ecule B. In the crystal, O—H⋯N hydrogen bonds link the components into [010] chains of alternating A and B mol­ecules. The chains are cross-linked by C—H⋯F hydrogen bonds and weak C—H⋯π and C—Cl⋯π [Cl⋯ring centroid = 3.7630 (8) Å] inter­actions, generating a three-dimensional network.

1. Related literature

For information on the fungicidal properties of the title compound, see: Demirci et al. (2011[Demirci, F., Muştu, M., Kaydan, M. B. & Ülgentürk, S. (2011). Phytoparasitica, 39, 353-360.]). For related crystal structures, see: Albinati et al. (1988[Albinati, A., Meille, S. V., Arnoldi, A. & Merlini, L. (1988). Acta Cryst. C44, 1782-1784.]); Caruso & Rossi (1998[Caruso, F. & Rossi, M. (1998). Acta Cryst. C54, 1668-1670.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H12ClFN2O

  • Mr = 314.74

  • Monoclinic, P 21 /n

  • a = 13.5772 (5) Å

  • b = 9.3722 (4) Å

  • c = 22.8756 (10) Å

  • β = 99.974 (2)°

  • V = 2866.9 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 173 K

  • 0.23 × 0.19 × 0.02 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 = 0.938, Tmax = 0.994

  • 49181 measured reflections

  • 6552 independent reflections

  • 5243 reflections with I > 2σ(I)

  • Rint = 0.048

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.094

  • S = 1.02

  • 6552 reflections

  • 399 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N3i 0.84 2.05 2.8876 (17) 176
O2—H2⋯N1 0.84 1.95 2.7807 (16) 169
C10—H10⋯F2ii 0.95 2.33 3.0247 (19) 130
C11—H11⋯F1iii 0.95 2.49 3.1683 (18) 128
C9—H9⋯Cg1 0.95 2.60 3.4568 (17) 149
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y+1, z.

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


Comment top

Nuarimol, (RS)-2-chloro-4'-fluoro-α-(pyrimidin-5-yl)benzhydryl alcohol, is a systemic pyrimidine fungicide, which has an effect on both conidial germination and mycelial growth (Demirci et al., 2011). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), dihedral angles between the planes of the pyrimidine ring and the chlorophenyl and fluorophenyl ring planes are 71.10 (6), 70.04 (5) in A, 73.24 (5), and 89.30 (5)° in B, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Albinati et al., 1988; Caruso et al., 1998).

In the crystal structure (Fig. 2), O–H···N and C–H···F hydrogen bonds and weak C–H···Cg1 interactions are observed (Table 1). In addition, weak intermolecular C19–Cl2···Cg1i (Cg1 is the centroid of the C18–C23 ring) interaction with a chlorophenyl ring is present [for symmetry code: (i), -x + 3/2, y + 1/2, -z + 1/2]. A three-dimensional network is formed by the hydrogen bond and these interactions.

Related literature top

For information on the fungicidal properties of the title compound, see: Demirci et al. (2011). For related crystal structures, see: Albinati et al. (1988); Caruso & Rossi (1998).

Experimental top

The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3CN gave single crystals suitable for X-ray analysis in the form of colourless blocks.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(O—H) = 0.84 Å, Uiso = 1.2Ueq(C) for O—H group and d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Structure description top

Nuarimol, (RS)-2-chloro-4'-fluoro-α-(pyrimidin-5-yl)benzhydryl alcohol, is a systemic pyrimidine fungicide, which has an effect on both conidial germination and mycelial growth (Demirci et al., 2011). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), dihedral angles between the planes of the pyrimidine ring and the chlorophenyl and fluorophenyl ring planes are 71.10 (6), 70.04 (5) in A, 73.24 (5), and 89.30 (5)° in B, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Albinati et al., 1988; Caruso et al., 1998).

In the crystal structure (Fig. 2), O–H···N and C–H···F hydrogen bonds and weak C–H···Cg1 interactions are observed (Table 1). In addition, weak intermolecular C19–Cl2···Cg1i (Cg1 is the centroid of the C18–C23 ring) interaction with a chlorophenyl ring is present [for symmetry code: (i), -x + 3/2, y + 1/2, -z + 1/2]. A three-dimensional network is formed by the hydrogen bond and these interactions.

For information on the fungicidal properties of the title compound, see: Demirci et al. (2011). For related crystal structures, see: Albinati et al. (1988); Caruso & Rossi (1998).

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 displacement ellipsoids 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.
(RS)-(2-Chlorophenyl)(4-fluorophenyl)(pyrimidin-5-yl)methanol top
Crystal data top
C17H12ClFN2OF(000) = 1296
Mr = 314.74Dx = 1.458 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.5772 (5) ÅCell parameters from 9868 reflections
b = 9.3722 (4) Åθ = 2.4–27.4°
c = 22.8756 (10) ŵ = 0.28 mm1
β = 99.974 (2)°T = 173 K
V = 2866.9 (2) Å3Block, colourless
Z = 80.23 × 0.19 × 0.02 mm
Data collection top
Bruker APEXII CCD
diffractometer
5243 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
θmax = 27.5°, θmin = 1.6°
Tmin = 0.938, Tmax = 0.994h = 1715
49181 measured reflectionsk = 1212
6552 independent reflectionsl = 2629
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0373P)2 + 1.2482P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6552 reflectionsΔρmax = 0.30 e Å3
399 parametersΔρmin = 0.33 e Å3
Crystal data top
C17H12ClFN2OV = 2866.9 (2) Å3
Mr = 314.74Z = 8
Monoclinic, P21/nMo Kα radiation
a = 13.5772 (5) ŵ = 0.28 mm1
b = 9.3722 (4) ÅT = 173 K
c = 22.8756 (10) Å0.23 × 0.19 × 0.02 mm
β = 99.974 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
6552 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
5243 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.994Rint = 0.048
49181 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å3
6552 reflectionsΔρmin = 0.33 e Å3
399 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
Cl10.63147 (3)1.08339 (5)0.58828 (2)0.03329 (11)
Cl20.76439 (3)0.87663 (5)0.24544 (2)0.04037 (12)
F10.63952 (9)0.43385 (10)0.56060 (5)0.0435 (3)
F20.10747 (8)0.85446 (14)0.18266 (6)0.0578 (3)
O10.84803 (8)0.94613 (11)0.46184 (5)0.0252 (2)
H10.86381.02270.44670.038*
O20.55752 (8)1.03372 (10)0.23794 (4)0.0252 (2)
H20.56411.04490.27480.038*
N10.59896 (11)1.09694 (14)0.35847 (6)0.0306 (3)
N20.63234 (10)1.29702 (14)0.42266 (6)0.0290 (3)
N30.59877 (10)0.71612 (15)0.08495 (6)0.0307 (3)
N40.56029 (11)0.96125 (15)0.06519 (6)0.0328 (3)
C10.81585 (11)1.04686 (15)0.55498 (6)0.0215 (3)
C20.76148 (12)1.09722 (16)0.59716 (7)0.0249 (3)
C30.80810 (14)1.16167 (18)0.64950 (7)0.0347 (4)
H30.76911.19700.67700.042*
C40.91094 (15)1.17431 (19)0.66147 (8)0.0396 (4)
H40.94291.21770.69730.048*
C50.96701 (14)1.12369 (18)0.62112 (8)0.0346 (4)
H51.03781.13120.62920.041*
C60.91950 (12)1.06180 (16)0.56867 (7)0.0273 (3)
H60.95901.02840.54110.033*
C70.77056 (11)0.97330 (15)0.49555 (6)0.0214 (3)
C80.69528 (11)1.06668 (15)0.45545 (6)0.0212 (3)
C90.64915 (12)1.01376 (17)0.40093 (7)0.0278 (3)
H90.65340.91440.39350.033*
C100.59480 (12)1.23530 (17)0.37161 (7)0.0299 (4)
H100.56141.29580.34120.036*
C110.68292 (12)1.21098 (16)0.46406 (7)0.0249 (3)
H110.71171.25120.50120.030*
C120.73077 (11)0.82590 (15)0.50925 (6)0.0218 (3)
C130.62998 (12)0.79740 (16)0.50815 (7)0.0263 (3)
H130.58190.86980.49590.032*
C140.59850 (13)0.66483 (17)0.52473 (7)0.0310 (4)
H140.52960.64550.52410.037*
C150.66972 (14)0.56261 (16)0.54209 (7)0.0303 (4)
C160.76940 (13)0.58404 (17)0.54206 (7)0.0311 (4)
H160.81650.50960.55310.037*
C170.80007 (12)0.71699 (16)0.52556 (7)0.0274 (3)
H170.86900.73410.52540.033*
C180.58321 (11)0.78920 (15)0.27131 (6)0.0223 (3)
C190.68755 (12)0.77899 (16)0.28450 (7)0.0265 (3)
C200.73552 (13)0.69367 (17)0.33029 (7)0.0322 (4)
H200.80640.68770.33780.039*
C210.68046 (14)0.61731 (17)0.36501 (7)0.0325 (4)
H210.71330.55940.39650.039*
C220.57749 (14)0.62565 (17)0.35365 (7)0.0314 (4)
H220.53910.57360.37740.038*
C230.52998 (12)0.71057 (16)0.30732 (7)0.0265 (3)
H230.45900.71520.30000.032*
C240.52929 (11)0.89043 (15)0.22322 (6)0.0212 (3)
C250.55638 (11)0.86464 (15)0.16185 (6)0.0216 (3)
C260.58502 (12)0.73512 (17)0.14135 (7)0.0272 (3)
H260.59540.65660.16800.033*
C270.58488 (13)0.83070 (19)0.05016 (7)0.0331 (4)
H270.59350.81780.01020.040*
C280.54549 (12)0.97556 (17)0.12101 (7)0.0262 (3)
H280.52651.06660.13350.031*
C290.41437 (11)0.87642 (15)0.21441 (6)0.0213 (3)
C300.36495 (12)0.75843 (17)0.18589 (7)0.0282 (3)
H300.40300.68240.17360.034*
C310.26178 (13)0.75007 (18)0.17516 (7)0.0318 (4)
H310.22860.66920.15590.038*
C320.20876 (12)0.86111 (19)0.19289 (7)0.0337 (4)
C330.25363 (13)0.97840 (19)0.22114 (8)0.0384 (4)
H330.21471.05380.23310.046*
C340.35716 (13)0.98521 (18)0.23203 (7)0.0312 (4)
H340.38941.06600.25190.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0317 (2)0.0379 (2)0.0325 (2)0.00085 (17)0.01153 (17)0.00473 (17)
Cl20.0281 (2)0.0486 (3)0.0437 (3)0.00338 (19)0.00418 (18)0.0138 (2)
F10.0620 (7)0.0226 (5)0.0485 (6)0.0083 (5)0.0167 (5)0.0002 (4)
F20.0242 (6)0.0786 (9)0.0697 (8)0.0000 (6)0.0055 (5)0.0044 (7)
O10.0256 (6)0.0270 (6)0.0240 (6)0.0028 (5)0.0070 (4)0.0001 (4)
O20.0362 (6)0.0189 (5)0.0183 (5)0.0040 (4)0.0011 (5)0.0018 (4)
N10.0362 (8)0.0295 (7)0.0226 (7)0.0029 (6)0.0042 (6)0.0005 (6)
N20.0334 (8)0.0243 (7)0.0278 (7)0.0059 (6)0.0010 (6)0.0006 (6)
N30.0335 (8)0.0334 (8)0.0267 (7)0.0027 (6)0.0089 (6)0.0052 (6)
N40.0407 (8)0.0354 (8)0.0210 (7)0.0037 (6)0.0019 (6)0.0014 (6)
C10.0261 (8)0.0173 (7)0.0203 (7)0.0007 (6)0.0013 (6)0.0026 (6)
C20.0300 (8)0.0215 (7)0.0230 (8)0.0008 (6)0.0037 (6)0.0014 (6)
C30.0491 (11)0.0319 (9)0.0230 (8)0.0022 (8)0.0064 (8)0.0061 (7)
C40.0514 (12)0.0354 (10)0.0270 (9)0.0085 (8)0.0072 (8)0.0073 (7)
C50.0325 (9)0.0314 (9)0.0353 (9)0.0058 (7)0.0067 (7)0.0004 (7)
C60.0281 (8)0.0265 (8)0.0257 (8)0.0007 (6)0.0004 (6)0.0010 (6)
C70.0216 (7)0.0227 (7)0.0192 (7)0.0027 (6)0.0021 (6)0.0012 (6)
C80.0223 (7)0.0227 (7)0.0184 (7)0.0016 (6)0.0032 (6)0.0005 (6)
C90.0341 (9)0.0221 (8)0.0251 (8)0.0023 (7)0.0005 (7)0.0013 (6)
C100.0308 (9)0.0303 (9)0.0266 (8)0.0064 (7)0.0012 (7)0.0030 (7)
C110.0283 (8)0.0240 (8)0.0216 (7)0.0017 (6)0.0025 (6)0.0018 (6)
C120.0262 (8)0.0203 (7)0.0177 (7)0.0010 (6)0.0008 (6)0.0032 (6)
C130.0267 (8)0.0245 (8)0.0272 (8)0.0019 (6)0.0030 (6)0.0026 (6)
C140.0310 (9)0.0292 (9)0.0341 (9)0.0055 (7)0.0090 (7)0.0070 (7)
C150.0459 (10)0.0188 (8)0.0269 (8)0.0057 (7)0.0087 (7)0.0043 (6)
C160.0380 (10)0.0221 (8)0.0316 (9)0.0052 (7)0.0013 (7)0.0005 (7)
C170.0273 (8)0.0248 (8)0.0287 (8)0.0025 (6)0.0005 (7)0.0017 (6)
C180.0288 (8)0.0189 (7)0.0184 (7)0.0000 (6)0.0013 (6)0.0017 (6)
C190.0300 (8)0.0230 (8)0.0259 (8)0.0008 (6)0.0031 (6)0.0015 (6)
C200.0322 (9)0.0265 (8)0.0347 (9)0.0057 (7)0.0035 (7)0.0001 (7)
C210.0441 (10)0.0227 (8)0.0273 (8)0.0053 (7)0.0033 (7)0.0036 (6)
C220.0458 (10)0.0239 (8)0.0239 (8)0.0028 (7)0.0045 (7)0.0048 (6)
C230.0303 (8)0.0253 (8)0.0231 (8)0.0022 (7)0.0023 (6)0.0000 (6)
C240.0269 (8)0.0176 (7)0.0183 (7)0.0012 (6)0.0015 (6)0.0009 (5)
C250.0207 (7)0.0235 (7)0.0194 (7)0.0028 (6)0.0006 (6)0.0014 (6)
C260.0317 (9)0.0261 (8)0.0242 (8)0.0015 (7)0.0060 (7)0.0005 (6)
C270.0374 (10)0.0417 (10)0.0210 (8)0.0070 (8)0.0076 (7)0.0043 (7)
C280.0298 (8)0.0253 (8)0.0217 (8)0.0010 (6)0.0003 (6)0.0005 (6)
C290.0267 (8)0.0213 (7)0.0154 (7)0.0012 (6)0.0023 (6)0.0027 (6)
C300.0304 (9)0.0261 (8)0.0275 (8)0.0005 (7)0.0037 (7)0.0046 (6)
C310.0309 (9)0.0358 (9)0.0272 (8)0.0071 (7)0.0010 (7)0.0041 (7)
C320.0236 (8)0.0467 (10)0.0305 (9)0.0011 (7)0.0040 (7)0.0064 (8)
C330.0355 (10)0.0344 (10)0.0483 (11)0.0073 (8)0.0155 (8)0.0017 (8)
C340.0346 (9)0.0267 (8)0.0337 (9)0.0008 (7)0.0096 (7)0.0057 (7)
Geometric parameters (Å, º) top
Cl1—C21.7464 (16)C13—C141.388 (2)
Cl2—C191.7456 (16)C13—H130.9500
F1—C151.3653 (18)C14—C151.370 (2)
F2—C321.3560 (19)C14—H140.9500
O1—C71.4307 (17)C15—C161.368 (2)
O1—H10.8400C16—C171.387 (2)
O2—C241.4209 (17)C16—H160.9500
O2—H20.8400C17—H170.9500
N1—C101.335 (2)C18—C231.397 (2)
N1—C91.337 (2)C18—C191.400 (2)
N2—C101.324 (2)C18—C241.538 (2)
N2—C111.3392 (19)C19—C201.387 (2)
N3—C271.331 (2)C20—C211.381 (2)
N3—C261.347 (2)C20—H200.9500
N4—C271.329 (2)C21—C221.379 (3)
N4—C281.333 (2)C21—H210.9500
C1—C61.395 (2)C22—C231.391 (2)
C1—C21.395 (2)C22—H220.9500
C1—C71.553 (2)C23—H230.9500
C2—C31.392 (2)C24—C251.531 (2)
C3—C41.381 (3)C24—C291.544 (2)
C3—H30.9500C25—C261.381 (2)
C4—C51.378 (3)C25—C281.388 (2)
C4—H40.9500C26—H260.9500
C5—C61.387 (2)C27—H270.9500
C5—H50.9500C28—H280.9500
C6—H60.9500C29—C341.383 (2)
C7—C81.526 (2)C29—C301.395 (2)
C7—C121.535 (2)C30—C311.382 (2)
C8—C111.381 (2)C30—H300.9500
C8—C91.387 (2)C31—C321.366 (2)
C9—H90.9500C31—H310.9500
C10—H100.9500C32—C331.364 (3)
C11—H110.9500C33—C341.386 (2)
C12—C131.390 (2)C33—H330.9500
C12—C171.395 (2)C34—H340.9500
C7—O1—H1109.5C16—C17—C12120.66 (15)
C24—O2—H2109.5C16—C17—H17119.7
C10—N1—C9116.05 (13)C12—C17—H17119.7
C10—N2—C11115.64 (13)C23—C18—C19116.40 (14)
C27—N3—C26115.93 (14)C23—C18—C24121.09 (14)
C27—N4—C28115.25 (14)C19—C18—C24122.33 (13)
C6—C1—C2116.42 (14)C20—C19—C18121.84 (15)
C6—C1—C7118.18 (13)C20—C19—Cl2116.40 (13)
C2—C1—C7125.38 (13)C18—C19—Cl2121.75 (12)
C3—C2—C1121.72 (15)C21—C20—C19120.19 (16)
C3—C2—Cl1115.60 (13)C21—C20—H20119.9
C1—C2—Cl1122.68 (12)C19—C20—H20119.9
C4—C3—C2120.09 (16)C22—C21—C20119.62 (15)
C4—C3—H3120.0C22—C21—H21120.2
C2—C3—H3120.0C20—C21—H21120.2
C5—C4—C3119.64 (15)C21—C22—C23119.81 (16)
C5—C4—H4120.2C21—C22—H22120.1
C3—C4—H4120.2C23—C22—H22120.1
C4—C5—C6119.68 (17)C22—C23—C18122.15 (15)
C4—C5—H5120.2C22—C23—H23118.9
C6—C5—H5120.2C18—C23—H23118.9
C5—C6—C1122.42 (16)O2—C24—C25105.59 (11)
C5—C6—H6118.8O2—C24—C18109.76 (11)
C1—C6—H6118.8C25—C24—C18113.46 (12)
O1—C7—C8104.86 (11)O2—C24—C29109.65 (12)
O1—C7—C12105.51 (11)C25—C24—C29105.35 (11)
C8—C7—C12114.59 (12)C18—C24—C29112.69 (12)
O1—C7—C1109.53 (12)C26—C25—C28115.66 (14)
C8—C7—C1113.22 (12)C26—C25—C24125.21 (13)
C12—C7—C1108.71 (11)C28—C25—C24118.97 (13)
C11—C8—C9115.56 (14)N3—C26—C25122.36 (14)
C11—C8—C7124.14 (13)N3—C26—H26118.8
C9—C8—C7119.13 (13)C25—C26—H26118.8
N1—C9—C8122.61 (14)N4—C27—N3127.17 (15)
N1—C9—H9118.7N4—C27—H27116.4
C8—C9—H9118.7N3—C27—H27116.4
N2—C10—N1126.77 (14)N4—C28—C25123.58 (15)
N2—C10—H10116.6N4—C28—H28118.2
N1—C10—H10116.6C25—C28—H28118.2
N2—C11—C8123.29 (14)C34—C29—C30118.14 (15)
N2—C11—H11118.4C34—C29—C24120.33 (13)
C8—C11—H11118.4C30—C29—C24121.44 (13)
C13—C12—C17118.72 (14)C31—C30—C29121.23 (15)
C13—C12—C7123.32 (13)C31—C30—H30119.4
C17—C12—C7117.92 (14)C29—C30—H30119.4
C14—C13—C12121.05 (15)C32—C31—C30118.30 (15)
C14—C13—H13119.5C32—C31—H31120.9
C12—C13—H13119.5C30—C31—H31120.9
C15—C14—C13118.02 (16)F2—C32—C33118.37 (16)
C15—C14—H14121.0F2—C32—C31118.98 (16)
C13—C14—H14121.0C33—C32—C31122.65 (16)
F1—C15—C16118.70 (15)C32—C33—C34118.56 (16)
F1—C15—C14118.23 (16)C32—C33—H33120.7
C16—C15—C14123.07 (15)C34—C33—H33120.7
C15—C16—C17118.41 (15)C29—C34—C33121.12 (15)
C15—C16—H16120.8C29—C34—H34119.4
C17—C16—H16120.8C33—C34—H34119.4
C6—C1—C2—C31.3 (2)C23—C18—C19—C201.0 (2)
C7—C1—C2—C3179.80 (14)C24—C18—C19—C20176.13 (14)
C6—C1—C2—Cl1178.40 (11)C23—C18—C19—Cl2177.32 (11)
C7—C1—C2—Cl10.1 (2)C24—C18—C19—Cl22.2 (2)
C1—C2—C3—C41.5 (2)C18—C19—C20—C211.0 (2)
Cl1—C2—C3—C4178.29 (13)Cl2—C19—C20—C21177.38 (13)
C2—C3—C4—C50.4 (3)C19—C20—C21—C220.4 (2)
C3—C4—C5—C60.6 (3)C20—C21—C22—C230.1 (2)
C4—C5—C6—C10.7 (3)C21—C22—C23—C180.1 (2)
C2—C1—C6—C50.2 (2)C19—C18—C23—C220.4 (2)
C7—C1—C6—C5178.83 (14)C24—C18—C23—C22175.65 (14)
C6—C1—C7—O15.94 (18)C23—C18—C24—O2114.19 (15)
C2—C1—C7—O1175.61 (13)C19—C18—C24—O260.75 (18)
C6—C1—C7—C8122.57 (14)C23—C18—C24—C25127.96 (15)
C2—C1—C7—C858.98 (19)C19—C18—C24—C2557.10 (18)
C6—C1—C7—C12108.87 (15)C23—C18—C24—C298.33 (19)
C2—C1—C7—C1269.58 (17)C19—C18—C24—C29176.73 (13)
O1—C7—C8—C11106.42 (16)O2—C24—C25—C26149.18 (14)
C12—C7—C8—C11138.39 (15)C18—C24—C25—C2628.9 (2)
C1—C7—C8—C1112.9 (2)C29—C24—C25—C2694.79 (17)
O1—C7—C8—C960.67 (17)O2—C24—C25—C2835.57 (18)
C12—C7—C8—C954.52 (19)C18—C24—C25—C28155.81 (13)
C1—C7—C8—C9179.99 (13)C29—C24—C25—C2880.46 (16)
C10—N1—C9—C80.5 (2)C27—N3—C26—C251.2 (2)
C11—C8—C9—N12.3 (2)C28—C25—C26—N31.8 (2)
C7—C8—C9—N1165.84 (15)C24—C25—C26—N3173.55 (14)
C11—N2—C10—N12.9 (3)C28—N4—C27—N32.1 (3)
C9—N1—C10—N22.3 (3)C26—N3—C27—N40.9 (3)
C10—N2—C11—C80.7 (2)C27—N4—C28—C251.2 (2)
C9—C8—C11—N21.7 (2)C26—C25—C28—N40.6 (2)
C7—C8—C11—N2165.81 (15)C24—C25—C28—N4175.13 (14)
O1—C7—C12—C13140.63 (14)O2—C24—C29—C3412.53 (18)
C8—C7—C12—C1325.8 (2)C25—C24—C29—C34125.73 (14)
C1—C7—C12—C13101.97 (16)C18—C24—C29—C34110.05 (15)
O1—C7—C12—C1741.66 (17)O2—C24—C29—C30164.03 (13)
C8—C7—C12—C17156.47 (13)C25—C24—C29—C3050.83 (17)
C1—C7—C12—C1775.74 (16)C18—C24—C29—C3073.39 (17)
C17—C12—C13—C142.0 (2)C34—C29—C30—C310.3 (2)
C7—C12—C13—C14175.65 (14)C24—C29—C30—C31176.34 (14)
C12—C13—C14—C150.2 (2)C29—C30—C31—C320.4 (2)
C13—C14—C15—F1177.54 (14)C30—C31—C32—F2180.00 (15)
C13—C14—C15—C162.0 (2)C30—C31—C32—C330.7 (3)
F1—C15—C16—C17177.36 (14)F2—C32—C33—C34179.58 (16)
C14—C15—C16—C172.2 (2)C31—C32—C33—C340.3 (3)
C15—C16—C17—C120.2 (2)C30—C29—C34—C330.7 (2)
C13—C12—C17—C161.9 (2)C24—C29—C34—C33175.94 (15)
C7—C12—C17—C16175.96 (14)C32—C33—C34—C290.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C18–C23 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N3i0.842.052.8876 (17)176
O2—H2···N10.841.952.7807 (16)169
C10—H10···F2ii0.952.333.0247 (19)130
C11—H11···F1iii0.952.493.1683 (18)128
C9—H9···Cg10.952.603.4568 (17)149
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C18–C23 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N3i0.842.052.8876 (17)176
O2—H2···N10.841.952.7807 (16)169
C10—H10···F2ii0.952.333.0247 (19)130
C11—H11···F1iii0.952.493.1683 (18)128
C9—H9···Cg10.952.603.4568 (17)149
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z.
 

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. 2014R1A1A4A01009105).

References

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