organic compounds
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
The title compound [systematic name: (RS)-(2-chlorophenyl)(4-fluorophenyl)(pyrimidin-5-yl)methanol], C17H12ClFN2O, is a pyrimidine fungicide. The 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.
Keywords: crystal structure; nuarimol; pyrimidine fungicide; hydrogen bonding.
CCDC reference: 1412613
1. Related literature
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).
2. Experimental
2.1. Crystal data
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2.3. Refinement
|
Data collection: APEX2 (Bruker, 2013); cell 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).
Supporting information
CCDC reference: 1412613
https://doi.org/10.1107/S2056989015013493/hb7465sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013493/hb7465Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013493/hb7465Isup3.cml
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.
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.
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 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
(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).
Data collection: APEX2 (Bruker, 2013); cell
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).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. | |
Fig. 2. Crystal packing viewed along the a axis. The intermolecular interactions are shown as dashed lines. |
C17H12ClFN2O | F(000) = 1296 |
Mr = 314.74 | Dx = 1.458 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.5772 (5) Å | Cell parameters from 9868 reflections |
b = 9.3722 (4) Å | θ = 2.4–27.4° |
c = 22.8756 (10) Å | µ = 0.28 mm−1 |
β = 99.974 (2)° | T = 173 K |
V = 2866.9 (2) Å3 | Block, colourless |
Z = 8 | 0.23 × 0.19 × 0.02 mm |
Bruker APEXII CCD diffractometer | 5243 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.048 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | θmax = 27.5°, θmin = 1.6° |
Tmin = 0.938, Tmax = 0.994 | h = −17→15 |
49181 measured reflections | k = −12→12 |
6552 independent reflections | l = −26→29 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.30 e Å−3 |
399 parameters | Δρmin = −0.33 e Å−3 |
C17H12ClFN2O | V = 2866.9 (2) Å3 |
Mr = 314.74 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.5772 (5) Å | µ = 0.28 mm−1 |
b = 9.3722 (4) Å | T = 173 K |
c = 22.8756 (10) Å | 0.23 × 0.19 × 0.02 mm |
β = 99.974 (2)° |
Bruker APEXII CCD diffractometer | 6552 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 5243 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 0.994 | Rint = 0.048 |
49181 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.30 e Å−3 |
6552 reflections | Δρmin = −0.33 e Å−3 |
399 parameters |
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 | 0.63147 (3) | 1.08339 (5) | 0.58828 (2) | 0.03329 (11) | |
Cl2 | 0.76439 (3) | 0.87663 (5) | 0.24544 (2) | 0.04037 (12) | |
F1 | 0.63952 (9) | 0.43385 (10) | 0.56060 (5) | 0.0435 (3) | |
F2 | 0.10747 (8) | 0.85446 (14) | 0.18266 (6) | 0.0578 (3) | |
O1 | 0.84803 (8) | 0.94613 (11) | 0.46184 (5) | 0.0252 (2) | |
H1 | 0.8638 | 1.0227 | 0.4467 | 0.038* | |
O2 | 0.55752 (8) | 1.03372 (10) | 0.23794 (4) | 0.0252 (2) | |
H2 | 0.5641 | 1.0449 | 0.2748 | 0.038* | |
N1 | 0.59896 (11) | 1.09694 (14) | 0.35847 (6) | 0.0306 (3) | |
N2 | 0.63234 (10) | 1.29702 (14) | 0.42266 (6) | 0.0290 (3) | |
N3 | 0.59877 (10) | 0.71612 (15) | 0.08495 (6) | 0.0307 (3) | |
N4 | 0.56029 (11) | 0.96125 (15) | 0.06519 (6) | 0.0328 (3) | |
C1 | 0.81585 (11) | 1.04686 (15) | 0.55498 (6) | 0.0215 (3) | |
C2 | 0.76148 (12) | 1.09722 (16) | 0.59716 (7) | 0.0249 (3) | |
C3 | 0.80810 (14) | 1.16167 (18) | 0.64950 (7) | 0.0347 (4) | |
H3 | 0.7691 | 1.1970 | 0.6770 | 0.042* | |
C4 | 0.91094 (15) | 1.17431 (19) | 0.66147 (8) | 0.0396 (4) | |
H4 | 0.9429 | 1.2177 | 0.6973 | 0.048* | |
C5 | 0.96701 (14) | 1.12369 (18) | 0.62112 (8) | 0.0346 (4) | |
H5 | 1.0378 | 1.1312 | 0.6292 | 0.041* | |
C6 | 0.91950 (12) | 1.06180 (16) | 0.56867 (7) | 0.0273 (3) | |
H6 | 0.9590 | 1.0284 | 0.5411 | 0.033* | |
C7 | 0.77056 (11) | 0.97330 (15) | 0.49555 (6) | 0.0214 (3) | |
C8 | 0.69528 (11) | 1.06668 (15) | 0.45545 (6) | 0.0212 (3) | |
C9 | 0.64915 (12) | 1.01376 (17) | 0.40093 (7) | 0.0278 (3) | |
H9 | 0.6534 | 0.9144 | 0.3935 | 0.033* | |
C10 | 0.59480 (12) | 1.23530 (17) | 0.37161 (7) | 0.0299 (4) | |
H10 | 0.5614 | 1.2958 | 0.3412 | 0.036* | |
C11 | 0.68292 (12) | 1.21098 (16) | 0.46406 (7) | 0.0249 (3) | |
H11 | 0.7117 | 1.2512 | 0.5012 | 0.030* | |
C12 | 0.73077 (11) | 0.82590 (15) | 0.50925 (6) | 0.0218 (3) | |
C13 | 0.62998 (12) | 0.79740 (16) | 0.50815 (7) | 0.0263 (3) | |
H13 | 0.5819 | 0.8698 | 0.4959 | 0.032* | |
C14 | 0.59850 (13) | 0.66483 (17) | 0.52473 (7) | 0.0310 (4) | |
H14 | 0.5296 | 0.6455 | 0.5241 | 0.037* | |
C15 | 0.66972 (14) | 0.56261 (16) | 0.54209 (7) | 0.0303 (4) | |
C16 | 0.76940 (13) | 0.58404 (17) | 0.54206 (7) | 0.0311 (4) | |
H16 | 0.8165 | 0.5096 | 0.5531 | 0.037* | |
C17 | 0.80007 (12) | 0.71699 (16) | 0.52556 (7) | 0.0274 (3) | |
H17 | 0.8690 | 0.7341 | 0.5254 | 0.033* | |
C18 | 0.58321 (11) | 0.78920 (15) | 0.27131 (6) | 0.0223 (3) | |
C19 | 0.68755 (12) | 0.77899 (16) | 0.28450 (7) | 0.0265 (3) | |
C20 | 0.73552 (13) | 0.69367 (17) | 0.33029 (7) | 0.0322 (4) | |
H20 | 0.8064 | 0.6877 | 0.3378 | 0.039* | |
C21 | 0.68046 (14) | 0.61731 (17) | 0.36501 (7) | 0.0325 (4) | |
H21 | 0.7133 | 0.5594 | 0.3965 | 0.039* | |
C22 | 0.57749 (14) | 0.62565 (17) | 0.35365 (7) | 0.0314 (4) | |
H22 | 0.5391 | 0.5736 | 0.3774 | 0.038* | |
C23 | 0.52998 (12) | 0.71057 (16) | 0.30732 (7) | 0.0265 (3) | |
H23 | 0.4590 | 0.7152 | 0.3000 | 0.032* | |
C24 | 0.52929 (11) | 0.89043 (15) | 0.22322 (6) | 0.0212 (3) | |
C25 | 0.55638 (11) | 0.86464 (15) | 0.16185 (6) | 0.0216 (3) | |
C26 | 0.58502 (12) | 0.73512 (17) | 0.14135 (7) | 0.0272 (3) | |
H26 | 0.5954 | 0.6566 | 0.1680 | 0.033* | |
C27 | 0.58488 (13) | 0.83070 (19) | 0.05016 (7) | 0.0331 (4) | |
H27 | 0.5935 | 0.8178 | 0.0102 | 0.040* | |
C28 | 0.54549 (12) | 0.97556 (17) | 0.12101 (7) | 0.0262 (3) | |
H28 | 0.5265 | 1.0666 | 0.1335 | 0.031* | |
C29 | 0.41437 (11) | 0.87642 (15) | 0.21441 (6) | 0.0213 (3) | |
C30 | 0.36495 (12) | 0.75843 (17) | 0.18589 (7) | 0.0282 (3) | |
H30 | 0.4030 | 0.6824 | 0.1736 | 0.034* | |
C31 | 0.26178 (13) | 0.75007 (18) | 0.17516 (7) | 0.0318 (4) | |
H31 | 0.2286 | 0.6692 | 0.1559 | 0.038* | |
C32 | 0.20876 (12) | 0.86111 (19) | 0.19289 (7) | 0.0337 (4) | |
C33 | 0.25363 (13) | 0.97840 (19) | 0.22114 (8) | 0.0384 (4) | |
H33 | 0.2147 | 1.0538 | 0.2331 | 0.046* | |
C34 | 0.35716 (13) | 0.98521 (18) | 0.23203 (7) | 0.0312 (4) | |
H34 | 0.3894 | 1.0660 | 0.2519 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0317 (2) | 0.0379 (2) | 0.0325 (2) | 0.00085 (17) | 0.01153 (17) | −0.00473 (17) |
Cl2 | 0.0281 (2) | 0.0486 (3) | 0.0437 (3) | −0.00338 (19) | 0.00418 (18) | 0.0138 (2) |
F1 | 0.0620 (7) | 0.0226 (5) | 0.0485 (6) | −0.0083 (5) | 0.0167 (5) | 0.0002 (4) |
F2 | 0.0242 (6) | 0.0786 (9) | 0.0697 (8) | 0.0000 (6) | 0.0055 (5) | −0.0044 (7) |
O1 | 0.0256 (6) | 0.0270 (6) | 0.0240 (6) | 0.0028 (5) | 0.0070 (4) | 0.0001 (4) |
O2 | 0.0362 (6) | 0.0189 (5) | 0.0183 (5) | −0.0040 (4) | −0.0011 (5) | −0.0018 (4) |
N1 | 0.0362 (8) | 0.0295 (7) | 0.0226 (7) | 0.0029 (6) | −0.0042 (6) | −0.0005 (6) |
N2 | 0.0334 (8) | 0.0243 (7) | 0.0278 (7) | 0.0059 (6) | 0.0010 (6) | 0.0006 (6) |
N3 | 0.0335 (8) | 0.0334 (8) | 0.0267 (7) | −0.0027 (6) | 0.0089 (6) | −0.0052 (6) |
N4 | 0.0407 (8) | 0.0354 (8) | 0.0210 (7) | −0.0037 (6) | 0.0019 (6) | 0.0014 (6) |
C1 | 0.0261 (8) | 0.0173 (7) | 0.0203 (7) | 0.0007 (6) | 0.0013 (6) | 0.0026 (6) |
C2 | 0.0300 (8) | 0.0215 (7) | 0.0230 (8) | −0.0008 (6) | 0.0037 (6) | 0.0014 (6) |
C3 | 0.0491 (11) | 0.0319 (9) | 0.0230 (8) | −0.0022 (8) | 0.0064 (8) | −0.0061 (7) |
C4 | 0.0514 (12) | 0.0354 (10) | 0.0270 (9) | −0.0085 (8) | −0.0072 (8) | −0.0073 (7) |
C5 | 0.0325 (9) | 0.0314 (9) | 0.0353 (9) | −0.0058 (7) | −0.0067 (7) | −0.0004 (7) |
C6 | 0.0281 (8) | 0.0265 (8) | 0.0257 (8) | −0.0007 (6) | 0.0004 (6) | 0.0010 (6) |
C7 | 0.0216 (7) | 0.0227 (7) | 0.0192 (7) | 0.0027 (6) | 0.0021 (6) | −0.0012 (6) |
C8 | 0.0223 (7) | 0.0227 (7) | 0.0184 (7) | 0.0016 (6) | 0.0032 (6) | 0.0005 (6) |
C9 | 0.0341 (9) | 0.0221 (8) | 0.0251 (8) | 0.0023 (7) | −0.0005 (7) | −0.0013 (6) |
C10 | 0.0308 (9) | 0.0303 (9) | 0.0266 (8) | 0.0064 (7) | −0.0012 (7) | 0.0030 (7) |
C11 | 0.0283 (8) | 0.0240 (8) | 0.0216 (7) | 0.0017 (6) | 0.0025 (6) | −0.0018 (6) |
C12 | 0.0262 (8) | 0.0203 (7) | 0.0177 (7) | 0.0010 (6) | 0.0008 (6) | −0.0032 (6) |
C13 | 0.0267 (8) | 0.0245 (8) | 0.0272 (8) | 0.0019 (6) | 0.0030 (6) | −0.0026 (6) |
C14 | 0.0310 (9) | 0.0292 (9) | 0.0341 (9) | −0.0055 (7) | 0.0090 (7) | −0.0070 (7) |
C15 | 0.0459 (10) | 0.0188 (8) | 0.0269 (8) | −0.0057 (7) | 0.0087 (7) | −0.0043 (6) |
C16 | 0.0380 (10) | 0.0221 (8) | 0.0316 (9) | 0.0052 (7) | 0.0013 (7) | −0.0005 (7) |
C17 | 0.0273 (8) | 0.0248 (8) | 0.0287 (8) | 0.0025 (6) | 0.0005 (7) | −0.0017 (6) |
C18 | 0.0288 (8) | 0.0189 (7) | 0.0184 (7) | 0.0000 (6) | 0.0013 (6) | −0.0017 (6) |
C19 | 0.0300 (8) | 0.0230 (8) | 0.0259 (8) | −0.0008 (6) | 0.0031 (6) | 0.0015 (6) |
C20 | 0.0322 (9) | 0.0265 (8) | 0.0347 (9) | 0.0057 (7) | −0.0035 (7) | 0.0001 (7) |
C21 | 0.0441 (10) | 0.0227 (8) | 0.0273 (8) | 0.0053 (7) | −0.0033 (7) | 0.0036 (6) |
C22 | 0.0458 (10) | 0.0239 (8) | 0.0239 (8) | −0.0028 (7) | 0.0045 (7) | 0.0048 (6) |
C23 | 0.0303 (8) | 0.0253 (8) | 0.0231 (8) | −0.0022 (7) | 0.0023 (6) | 0.0000 (6) |
C24 | 0.0269 (8) | 0.0176 (7) | 0.0183 (7) | −0.0012 (6) | 0.0015 (6) | −0.0009 (5) |
C25 | 0.0207 (7) | 0.0235 (7) | 0.0194 (7) | −0.0028 (6) | 0.0006 (6) | −0.0014 (6) |
C26 | 0.0317 (9) | 0.0261 (8) | 0.0242 (8) | −0.0015 (7) | 0.0060 (7) | −0.0005 (6) |
C27 | 0.0374 (10) | 0.0417 (10) | 0.0210 (8) | −0.0070 (8) | 0.0076 (7) | −0.0043 (7) |
C28 | 0.0298 (8) | 0.0253 (8) | 0.0217 (8) | −0.0010 (6) | −0.0003 (6) | 0.0005 (6) |
C29 | 0.0267 (8) | 0.0213 (7) | 0.0154 (7) | 0.0012 (6) | 0.0023 (6) | 0.0027 (6) |
C30 | 0.0304 (9) | 0.0261 (8) | 0.0275 (8) | −0.0005 (7) | 0.0037 (7) | −0.0046 (6) |
C31 | 0.0309 (9) | 0.0358 (9) | 0.0272 (8) | −0.0071 (7) | 0.0010 (7) | −0.0041 (7) |
C32 | 0.0236 (8) | 0.0467 (10) | 0.0305 (9) | 0.0011 (7) | 0.0040 (7) | 0.0064 (8) |
C33 | 0.0355 (10) | 0.0344 (10) | 0.0483 (11) | 0.0073 (8) | 0.0155 (8) | −0.0017 (8) |
C34 | 0.0346 (9) | 0.0267 (8) | 0.0337 (9) | −0.0008 (7) | 0.0096 (7) | −0.0057 (7) |
Cl1—C2 | 1.7464 (16) | C13—C14 | 1.388 (2) |
Cl2—C19 | 1.7456 (16) | C13—H13 | 0.9500 |
F1—C15 | 1.3653 (18) | C14—C15 | 1.370 (2) |
F2—C32 | 1.3560 (19) | C14—H14 | 0.9500 |
O1—C7 | 1.4307 (17) | C15—C16 | 1.368 (2) |
O1—H1 | 0.8400 | C16—C17 | 1.387 (2) |
O2—C24 | 1.4209 (17) | C16—H16 | 0.9500 |
O2—H2 | 0.8400 | C17—H17 | 0.9500 |
N1—C10 | 1.335 (2) | C18—C23 | 1.397 (2) |
N1—C9 | 1.337 (2) | C18—C19 | 1.400 (2) |
N2—C10 | 1.324 (2) | C18—C24 | 1.538 (2) |
N2—C11 | 1.3392 (19) | C19—C20 | 1.387 (2) |
N3—C27 | 1.331 (2) | C20—C21 | 1.381 (2) |
N3—C26 | 1.347 (2) | C20—H20 | 0.9500 |
N4—C27 | 1.329 (2) | C21—C22 | 1.379 (3) |
N4—C28 | 1.333 (2) | C21—H21 | 0.9500 |
C1—C6 | 1.395 (2) | C22—C23 | 1.391 (2) |
C1—C2 | 1.395 (2) | C22—H22 | 0.9500 |
C1—C7 | 1.553 (2) | C23—H23 | 0.9500 |
C2—C3 | 1.392 (2) | C24—C25 | 1.531 (2) |
C3—C4 | 1.381 (3) | C24—C29 | 1.544 (2) |
C3—H3 | 0.9500 | C25—C26 | 1.381 (2) |
C4—C5 | 1.378 (3) | C25—C28 | 1.388 (2) |
C4—H4 | 0.9500 | C26—H26 | 0.9500 |
C5—C6 | 1.387 (2) | C27—H27 | 0.9500 |
C5—H5 | 0.9500 | C28—H28 | 0.9500 |
C6—H6 | 0.9500 | C29—C34 | 1.383 (2) |
C7—C8 | 1.526 (2) | C29—C30 | 1.395 (2) |
C7—C12 | 1.535 (2) | C30—C31 | 1.382 (2) |
C8—C11 | 1.381 (2) | C30—H30 | 0.9500 |
C8—C9 | 1.387 (2) | C31—C32 | 1.366 (2) |
C9—H9 | 0.9500 | C31—H31 | 0.9500 |
C10—H10 | 0.9500 | C32—C33 | 1.364 (3) |
C11—H11 | 0.9500 | C33—C34 | 1.386 (2) |
C12—C13 | 1.390 (2) | C33—H33 | 0.9500 |
C12—C17 | 1.395 (2) | C34—H34 | 0.9500 |
C7—O1—H1 | 109.5 | C16—C17—C12 | 120.66 (15) |
C24—O2—H2 | 109.5 | C16—C17—H17 | 119.7 |
C10—N1—C9 | 116.05 (13) | C12—C17—H17 | 119.7 |
C10—N2—C11 | 115.64 (13) | C23—C18—C19 | 116.40 (14) |
C27—N3—C26 | 115.93 (14) | C23—C18—C24 | 121.09 (14) |
C27—N4—C28 | 115.25 (14) | C19—C18—C24 | 122.33 (13) |
C6—C1—C2 | 116.42 (14) | C20—C19—C18 | 121.84 (15) |
C6—C1—C7 | 118.18 (13) | C20—C19—Cl2 | 116.40 (13) |
C2—C1—C7 | 125.38 (13) | C18—C19—Cl2 | 121.75 (12) |
C3—C2—C1 | 121.72 (15) | C21—C20—C19 | 120.19 (16) |
C3—C2—Cl1 | 115.60 (13) | C21—C20—H20 | 119.9 |
C1—C2—Cl1 | 122.68 (12) | C19—C20—H20 | 119.9 |
C4—C3—C2 | 120.09 (16) | C22—C21—C20 | 119.62 (15) |
C4—C3—H3 | 120.0 | C22—C21—H21 | 120.2 |
C2—C3—H3 | 120.0 | C20—C21—H21 | 120.2 |
C5—C4—C3 | 119.64 (15) | C21—C22—C23 | 119.81 (16) |
C5—C4—H4 | 120.2 | C21—C22—H22 | 120.1 |
C3—C4—H4 | 120.2 | C23—C22—H22 | 120.1 |
C4—C5—C6 | 119.68 (17) | C22—C23—C18 | 122.15 (15) |
C4—C5—H5 | 120.2 | C22—C23—H23 | 118.9 |
C6—C5—H5 | 120.2 | C18—C23—H23 | 118.9 |
C5—C6—C1 | 122.42 (16) | O2—C24—C25 | 105.59 (11) |
C5—C6—H6 | 118.8 | O2—C24—C18 | 109.76 (11) |
C1—C6—H6 | 118.8 | C25—C24—C18 | 113.46 (12) |
O1—C7—C8 | 104.86 (11) | O2—C24—C29 | 109.65 (12) |
O1—C7—C12 | 105.51 (11) | C25—C24—C29 | 105.35 (11) |
C8—C7—C12 | 114.59 (12) | C18—C24—C29 | 112.69 (12) |
O1—C7—C1 | 109.53 (12) | C26—C25—C28 | 115.66 (14) |
C8—C7—C1 | 113.22 (12) | C26—C25—C24 | 125.21 (13) |
C12—C7—C1 | 108.71 (11) | C28—C25—C24 | 118.97 (13) |
C11—C8—C9 | 115.56 (14) | N3—C26—C25 | 122.36 (14) |
C11—C8—C7 | 124.14 (13) | N3—C26—H26 | 118.8 |
C9—C8—C7 | 119.13 (13) | C25—C26—H26 | 118.8 |
N1—C9—C8 | 122.61 (14) | N4—C27—N3 | 127.17 (15) |
N1—C9—H9 | 118.7 | N4—C27—H27 | 116.4 |
C8—C9—H9 | 118.7 | N3—C27—H27 | 116.4 |
N2—C10—N1 | 126.77 (14) | N4—C28—C25 | 123.58 (15) |
N2—C10—H10 | 116.6 | N4—C28—H28 | 118.2 |
N1—C10—H10 | 116.6 | C25—C28—H28 | 118.2 |
N2—C11—C8 | 123.29 (14) | C34—C29—C30 | 118.14 (15) |
N2—C11—H11 | 118.4 | C34—C29—C24 | 120.33 (13) |
C8—C11—H11 | 118.4 | C30—C29—C24 | 121.44 (13) |
C13—C12—C17 | 118.72 (14) | C31—C30—C29 | 121.23 (15) |
C13—C12—C7 | 123.32 (13) | C31—C30—H30 | 119.4 |
C17—C12—C7 | 117.92 (14) | C29—C30—H30 | 119.4 |
C14—C13—C12 | 121.05 (15) | C32—C31—C30 | 118.30 (15) |
C14—C13—H13 | 119.5 | C32—C31—H31 | 120.9 |
C12—C13—H13 | 119.5 | C30—C31—H31 | 120.9 |
C15—C14—C13 | 118.02 (16) | F2—C32—C33 | 118.37 (16) |
C15—C14—H14 | 121.0 | F2—C32—C31 | 118.98 (16) |
C13—C14—H14 | 121.0 | C33—C32—C31 | 122.65 (16) |
F1—C15—C16 | 118.70 (15) | C32—C33—C34 | 118.56 (16) |
F1—C15—C14 | 118.23 (16) | C32—C33—H33 | 120.7 |
C16—C15—C14 | 123.07 (15) | C34—C33—H33 | 120.7 |
C15—C16—C17 | 118.41 (15) | C29—C34—C33 | 121.12 (15) |
C15—C16—H16 | 120.8 | C29—C34—H34 | 119.4 |
C17—C16—H16 | 120.8 | C33—C34—H34 | 119.4 |
C6—C1—C2—C3 | 1.3 (2) | C23—C18—C19—C20 | 1.0 (2) |
C7—C1—C2—C3 | 179.80 (14) | C24—C18—C19—C20 | 176.13 (14) |
C6—C1—C2—Cl1 | −178.40 (11) | C23—C18—C19—Cl2 | −177.32 (11) |
C7—C1—C2—Cl1 | 0.1 (2) | C24—C18—C19—Cl2 | −2.2 (2) |
C1—C2—C3—C4 | −1.5 (2) | C18—C19—C20—C21 | −1.0 (2) |
Cl1—C2—C3—C4 | 178.29 (13) | Cl2—C19—C20—C21 | 177.38 (13) |
C2—C3—C4—C5 | 0.4 (3) | C19—C20—C21—C22 | 0.4 (2) |
C3—C4—C5—C6 | 0.6 (3) | C20—C21—C22—C23 | 0.1 (2) |
C4—C5—C6—C1 | −0.7 (3) | C21—C22—C23—C18 | −0.1 (2) |
C2—C1—C6—C5 | −0.2 (2) | C19—C18—C23—C22 | −0.4 (2) |
C7—C1—C6—C5 | −178.83 (14) | C24—C18—C23—C22 | −175.65 (14) |
C6—C1—C7—O1 | −5.94 (18) | C23—C18—C24—O2 | 114.19 (15) |
C2—C1—C7—O1 | 175.61 (13) | C19—C18—C24—O2 | −60.75 (18) |
C6—C1—C7—C8 | −122.57 (14) | C23—C18—C24—C25 | −127.96 (15) |
C2—C1—C7—C8 | 58.98 (19) | C19—C18—C24—C25 | 57.10 (18) |
C6—C1—C7—C12 | 108.87 (15) | C23—C18—C24—C29 | −8.33 (19) |
C2—C1—C7—C12 | −69.58 (17) | C19—C18—C24—C29 | 176.73 (13) |
O1—C7—C8—C11 | −106.42 (16) | O2—C24—C25—C26 | 149.18 (14) |
C12—C7—C8—C11 | 138.39 (15) | C18—C24—C25—C26 | 28.9 (2) |
C1—C7—C8—C11 | 12.9 (2) | C29—C24—C25—C26 | −94.79 (17) |
O1—C7—C8—C9 | 60.67 (17) | O2—C24—C25—C28 | −35.57 (18) |
C12—C7—C8—C9 | −54.52 (19) | C18—C24—C25—C28 | −155.81 (13) |
C1—C7—C8—C9 | −179.99 (13) | C29—C24—C25—C28 | 80.46 (16) |
C10—N1—C9—C8 | −0.5 (2) | C27—N3—C26—C25 | 1.2 (2) |
C11—C8—C9—N1 | 2.3 (2) | C28—C25—C26—N3 | −1.8 (2) |
C7—C8—C9—N1 | −165.84 (15) | C24—C25—C26—N3 | 173.55 (14) |
C11—N2—C10—N1 | 2.9 (3) | C28—N4—C27—N3 | −2.1 (3) |
C9—N1—C10—N2 | −2.3 (3) | C26—N3—C27—N4 | 0.9 (3) |
C10—N2—C11—C8 | −0.7 (2) | C27—N4—C28—C25 | 1.2 (2) |
C9—C8—C11—N2 | −1.7 (2) | C26—C25—C28—N4 | 0.6 (2) |
C7—C8—C11—N2 | 165.81 (15) | C24—C25—C28—N4 | −175.13 (14) |
O1—C7—C12—C13 | −140.63 (14) | O2—C24—C29—C34 | −12.53 (18) |
C8—C7—C12—C13 | −25.8 (2) | C25—C24—C29—C34 | −125.73 (14) |
C1—C7—C12—C13 | 101.97 (16) | C18—C24—C29—C34 | 110.05 (15) |
O1—C7—C12—C17 | 41.66 (17) | O2—C24—C29—C30 | 164.03 (13) |
C8—C7—C12—C17 | 156.47 (13) | C25—C24—C29—C30 | 50.83 (17) |
C1—C7—C12—C17 | −75.74 (16) | C18—C24—C29—C30 | −73.39 (17) |
C17—C12—C13—C14 | 2.0 (2) | C34—C29—C30—C31 | 0.3 (2) |
C7—C12—C13—C14 | −175.65 (14) | C24—C29—C30—C31 | −176.34 (14) |
C12—C13—C14—C15 | −0.2 (2) | C29—C30—C31—C32 | 0.4 (2) |
C13—C14—C15—F1 | 177.54 (14) | C30—C31—C32—F2 | 180.00 (15) |
C13—C14—C15—C16 | −2.0 (2) | C30—C31—C32—C33 | −0.7 (3) |
F1—C15—C16—C17 | −177.36 (14) | F2—C32—C33—C34 | 179.58 (16) |
C14—C15—C16—C17 | 2.2 (2) | C31—C32—C33—C34 | 0.3 (3) |
C15—C16—C17—C12 | −0.2 (2) | C30—C29—C34—C33 | −0.7 (2) |
C13—C12—C17—C16 | −1.9 (2) | C24—C29—C34—C33 | 175.94 (15) |
C7—C12—C17—C16 | 175.96 (14) | C32—C33—C34—C29 | 0.5 (3) |
Cg1 is the centroid of the C18–C23 ring. |
D—H···A | D—H | H···A | D···A | 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+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z. |
Cg1 is the centroid of the C18–C23 ring. |
D—H···A | D—H | H···A | D···A | 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+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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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.