organic compounds
of fenbuconazole
aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang, National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr
In the title compound, C19H17ClN4 [systematic name: (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile], which is the conazole fungicide fenbuconazole, the dihedral angles between the planes of the central benzene and the terminal chlorophenyl and triazole rings are 32.77 (5) and 32.97 (5)°, respectively. The C—C—C—C linkage between the tertiary C atom and the benzene ring has an anti orientation [torsion angle = 174.47 (12)°]. In the crystal, C—H⋯N hydrogen bonds and very weak C—Cl⋯π interactions [Cl⋯π = 3.7892 (9) Å] link adjacent molecules, forming two-dimensional networks lying parellel to the (101) plane. The planes are linked by weak π–π interactions [centroid–centroid separation = 3.8597 (9) Å], resulting in a three-dimensional architecture.
Keywords: crystal structure; fungicide; fenbuconazole; C—Cl⋯π interactions; π–π interactions.
CCDC reference: 1419334
1. Related literature
For information on the fungicidal properties of the title compound, see: Li et al. (2012). For related crystal structures, see: Rizzoli et al. (2009); Yin et al. (2014).
2. Experimental
2.1. Crystal data
|
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: 1419334
https://doi.org/10.1107/S205698901501542X/hb7481sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901501542X/hb7481Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698901501542X/hb7481Isup3.cml
The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3CN gave brown plates suitable for X-ray analysis.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group and d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.
Fenbuconazole, [systematic name: (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile], is a conazole fungicide and it has been used for the control of leaf spot, yellow and brown rust, powdery mildew, and net blotch on various agricultural and horticultural crops (Li et al., 2012). However, until now its
has not been reported. The dihedral angles between the planes of the central benzene and the terminal chlorophenyl and triazole rings are 32.77 (5) and 32.97 (5)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Rizzoli et al., 2009; Yin et al., 2014).In the π···π interaction between the terminal chlorophenyl ring systems [Cg2···Cg2v, 3.8597 (9) Å], resulting in a three-dimensional architecture. (Cg2 is the centroid of the C1–C6 ring) [for symmetry codes: (iv), -x + 1, -y + 1, -z + 2, (v), -x, -y + 1, -z + 2].
(Fig. 2), C—H··· N hydrogen bonds and weak C3–Cl1···Cg1iv (Cg1 is the centroid of the N2–N3–C18–N4–C19 ring) interaction [3.7892 (9) Å] with a chlorophenyl ring are observed (Table 1), forming two-dimensional networks parelle to (101) plane. In addition, the planes are linked by weak intermolecularFor information on the fungicidal properties of the title compound, see: Li et al. (2012). For related crystal structures, see: Rizzoli et al. (2009); Yin et al. (2014).
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. | |
Fig. 2. Crystal packing viewed along the b axis. The intermolecular interactions are shown as dashed lines. |
C19H17ClN4 | F(000) = 704 |
Mr = 336.82 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.4606 (3) Å | Cell parameters from 3787 reflections |
b = 6.7404 (2) Å | θ = 3.2–27.4° |
c = 20.5394 (5) Å | µ = 0.23 mm−1 |
β = 95.455 (2)° | T = 173 K |
V = 1717.28 (8) Å3 | Plate, brown |
Z = 4 | 0.18 × 0.07 × 0.03 mm |
Bruker APEXII CCD diffractometer | 3044 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.035 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | θmax = 27.5°, θmin = 1.8° |
Tmin = 0.959, Tmax = 0.993 | h = −15→16 |
15784 measured reflections | k = −8→8 |
3936 independent reflections | l = −26→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.043P)2 + 0.4967P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3936 reflections | Δρmax = 0.25 e Å−3 |
217 parameters | Δρmin = −0.30 e Å−3 |
C19H17ClN4 | V = 1717.28 (8) Å3 |
Mr = 336.82 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.4606 (3) Å | µ = 0.23 mm−1 |
b = 6.7404 (2) Å | T = 173 K |
c = 20.5394 (5) Å | 0.18 × 0.07 × 0.03 mm |
β = 95.455 (2)° |
Bruker APEXII CCD diffractometer | 3936 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3044 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.993 | Rint = 0.035 |
15784 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.25 e Å−3 |
3936 reflections | Δρmin = −0.30 e Å−3 |
217 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 | 0.02411 (4) | 0.19334 (10) | 1.12090 (3) | 0.0689 (2) | |
N1 | 0.42210 (11) | 1.1422 (2) | 0.92410 (6) | 0.0367 (3) | |
N2 | 0.63664 (9) | 0.7989 (2) | 0.86689 (5) | 0.0277 (3) | |
N3 | 0.66105 (11) | 0.9948 (2) | 0.87314 (6) | 0.0398 (3) | |
N4 | 0.71532 (12) | 0.8721 (2) | 0.77946 (7) | 0.0445 (4) | |
C1 | 0.17939 (13) | 0.3822 (3) | 0.97206 (8) | 0.0384 (4) | |
H1 | 0.2005 | 0.3286 | 0.9325 | 0.046* | |
C2 | 0.12369 (14) | 0.2639 (3) | 1.01229 (9) | 0.0447 (4) | |
H2 | 0.1056 | 0.1311 | 1.0003 | 0.054* | |
C3 | 0.09501 (12) | 0.3415 (3) | 1.06994 (8) | 0.0410 (4) | |
C4 | 0.12079 (14) | 0.5320 (3) | 1.08810 (8) | 0.0485 (5) | |
H4 | 0.1014 | 0.5833 | 1.1284 | 0.058* | |
C5 | 0.17565 (13) | 0.6493 (3) | 1.04672 (8) | 0.0398 (4) | |
H5 | 0.1933 | 0.7822 | 1.0589 | 0.048* | |
C6 | 0.20501 (10) | 0.5763 (2) | 0.98807 (7) | 0.0278 (3) | |
C7 | 0.26520 (11) | 0.7035 (3) | 0.94298 (7) | 0.0316 (3) | |
H7A | 0.2559 | 0.8451 | 0.9541 | 0.038* | |
H7B | 0.2341 | 0.6831 | 0.8973 | 0.038* | |
C8 | 0.38533 (11) | 0.6541 (2) | 0.94830 (6) | 0.0237 (3) | |
H8A | 0.3937 | 0.5096 | 0.9418 | 0.028* | |
H8B | 0.4171 | 0.6864 | 0.9931 | 0.028* | |
C9 | 0.44939 (10) | 0.7655 (2) | 0.89855 (6) | 0.0218 (3) | |
C10 | 0.41229 (10) | 0.7205 (2) | 0.82676 (6) | 0.0229 (3) | |
C11 | 0.38360 (12) | 0.5284 (2) | 0.80795 (7) | 0.0312 (3) | |
H11 | 0.3807 | 0.4280 | 0.8402 | 0.037* | |
C12 | 0.35906 (13) | 0.4822 (3) | 0.74246 (7) | 0.0364 (4) | |
H12 | 0.3390 | 0.3506 | 0.7301 | 0.044* | |
C13 | 0.36370 (13) | 0.6264 (3) | 0.69533 (7) | 0.0369 (4) | |
H13 | 0.3467 | 0.5943 | 0.6505 | 0.044* | |
C14 | 0.39293 (13) | 0.8170 (3) | 0.71325 (7) | 0.0361 (4) | |
H14 | 0.3968 | 0.9162 | 0.6807 | 0.043* | |
C15 | 0.41687 (12) | 0.8646 (2) | 0.77900 (6) | 0.0297 (3) | |
H15 | 0.4364 | 0.9967 | 0.7912 | 0.036* | |
C16 | 0.43710 (11) | 0.9796 (2) | 0.91178 (6) | 0.0257 (3) | |
C17 | 0.56995 (11) | 0.7062 (2) | 0.91202 (6) | 0.0255 (3) | |
H17A | 0.5963 | 0.7450 | 0.9572 | 0.031* | |
H17B | 0.5765 | 0.5603 | 0.9086 | 0.031* | |
C18 | 0.70813 (15) | 1.0295 (3) | 0.81948 (8) | 0.0472 (5) | |
H18 | 0.7352 | 1.1567 | 0.8096 | 0.057* | |
C19 | 0.66923 (13) | 0.7306 (3) | 0.81087 (7) | 0.0357 (4) | |
H19 | 0.6603 | 0.5979 | 0.7958 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0454 (3) | 0.0820 (4) | 0.0822 (4) | −0.0076 (3) | 0.0220 (2) | 0.0428 (3) |
N1 | 0.0555 (8) | 0.0248 (8) | 0.0306 (7) | 0.0036 (7) | 0.0081 (6) | 0.0001 (6) |
N2 | 0.0283 (6) | 0.0304 (7) | 0.0253 (6) | −0.0013 (5) | 0.0069 (5) | 0.0004 (5) |
N3 | 0.0489 (8) | 0.0351 (8) | 0.0384 (7) | −0.0131 (7) | 0.0195 (6) | −0.0055 (6) |
N4 | 0.0514 (8) | 0.0463 (10) | 0.0397 (7) | −0.0003 (7) | 0.0240 (6) | 0.0004 (7) |
C1 | 0.0448 (9) | 0.0389 (10) | 0.0317 (8) | −0.0065 (8) | 0.0057 (6) | −0.0035 (7) |
C2 | 0.0441 (9) | 0.0366 (10) | 0.0529 (10) | −0.0123 (8) | 0.0020 (8) | 0.0032 (8) |
C3 | 0.0275 (7) | 0.0508 (12) | 0.0455 (9) | −0.0038 (8) | 0.0086 (6) | 0.0185 (8) |
C4 | 0.0521 (10) | 0.0585 (13) | 0.0388 (9) | −0.0014 (10) | 0.0241 (8) | 0.0008 (9) |
C5 | 0.0474 (9) | 0.0360 (10) | 0.0382 (8) | −0.0064 (8) | 0.0164 (7) | −0.0052 (7) |
C6 | 0.0231 (6) | 0.0334 (9) | 0.0271 (7) | 0.0002 (6) | 0.0036 (5) | 0.0036 (6) |
C7 | 0.0317 (7) | 0.0344 (9) | 0.0297 (7) | 0.0026 (7) | 0.0084 (6) | 0.0068 (7) |
C8 | 0.0299 (7) | 0.0226 (8) | 0.0193 (6) | −0.0001 (6) | 0.0054 (5) | 0.0023 (6) |
C9 | 0.0274 (6) | 0.0185 (7) | 0.0200 (6) | 0.0006 (6) | 0.0053 (5) | 0.0021 (5) |
C10 | 0.0243 (6) | 0.0246 (8) | 0.0202 (6) | 0.0026 (6) | 0.0046 (5) | 0.0004 (6) |
C11 | 0.0427 (8) | 0.0269 (9) | 0.0245 (7) | 0.0000 (7) | 0.0055 (6) | 0.0024 (6) |
C12 | 0.0482 (9) | 0.0306 (9) | 0.0302 (8) | 0.0004 (8) | 0.0024 (6) | −0.0069 (7) |
C13 | 0.0427 (8) | 0.0468 (11) | 0.0208 (7) | 0.0091 (8) | 0.0014 (6) | −0.0042 (7) |
C14 | 0.0465 (9) | 0.0397 (10) | 0.0223 (7) | 0.0063 (8) | 0.0045 (6) | 0.0075 (7) |
C15 | 0.0385 (8) | 0.0267 (9) | 0.0242 (7) | 0.0014 (7) | 0.0036 (6) | 0.0038 (6) |
C16 | 0.0334 (7) | 0.0257 (9) | 0.0186 (6) | −0.0012 (7) | 0.0053 (5) | 0.0032 (6) |
C17 | 0.0288 (7) | 0.0262 (8) | 0.0220 (6) | 0.0010 (6) | 0.0048 (5) | 0.0036 (6) |
C18 | 0.0574 (11) | 0.0420 (11) | 0.0467 (9) | −0.0119 (9) | 0.0284 (8) | −0.0007 (8) |
C19 | 0.0392 (8) | 0.0379 (10) | 0.0322 (8) | 0.0044 (7) | 0.0142 (6) | −0.0043 (7) |
Cl1—C3 | 1.7461 (16) | C8—C9 | 1.5492 (18) |
N1—C16 | 1.1445 (19) | C8—H8A | 0.9900 |
N2—C19 | 1.3376 (18) | C8—H8B | 0.9900 |
N2—N3 | 1.3585 (18) | C9—C16 | 1.479 (2) |
N2—C17 | 1.4444 (17) | C9—C10 | 1.5332 (17) |
N3—C18 | 1.3178 (19) | C9—C17 | 1.5537 (18) |
N4—C19 | 1.314 (2) | C10—C15 | 1.386 (2) |
N4—C18 | 1.351 (2) | C10—C11 | 1.388 (2) |
C1—C6 | 1.379 (2) | C11—C12 | 1.386 (2) |
C1—C2 | 1.382 (2) | C11—H11 | 0.9500 |
C1—H1 | 0.9500 | C12—C13 | 1.377 (2) |
C2—C3 | 1.372 (2) | C12—H12 | 0.9500 |
C2—H2 | 0.9500 | C13—C14 | 1.376 (2) |
C3—C4 | 1.367 (3) | C13—H13 | 0.9500 |
C4—C5 | 1.388 (2) | C14—C15 | 1.392 (2) |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.382 (2) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C17—H17A | 0.9900 |
C6—C7 | 1.5124 (19) | C17—H17B | 0.9900 |
C7—C8 | 1.5273 (19) | C18—H18 | 0.9500 |
C7—H7A | 0.9900 | C19—H19 | 0.9500 |
C7—H7B | 0.9900 | ||
C19—N2—N3 | 109.39 (12) | C16—C9—C8 | 106.43 (11) |
C19—N2—C17 | 130.06 (14) | C10—C9—C8 | 114.28 (11) |
N3—N2—C17 | 119.81 (12) | C16—C9—C17 | 109.49 (12) |
C18—N3—N2 | 101.96 (13) | C10—C9—C17 | 108.56 (10) |
C19—N4—C18 | 102.36 (13) | C8—C9—C17 | 107.94 (10) |
C6—C1—C2 | 121.52 (15) | C15—C10—C11 | 118.93 (13) |
C6—C1—H1 | 119.2 | C15—C10—C9 | 120.87 (13) |
C2—C1—H1 | 119.2 | C11—C10—C9 | 119.90 (12) |
C3—C2—C1 | 118.87 (17) | C12—C11—C10 | 120.47 (14) |
C3—C2—H2 | 120.6 | C12—C11—H11 | 119.8 |
C1—C2—H2 | 120.6 | C10—C11—H11 | 119.8 |
C4—C3—C2 | 121.31 (15) | C13—C12—C11 | 120.22 (16) |
C4—C3—Cl1 | 119.53 (14) | C13—C12—H12 | 119.9 |
C2—C3—Cl1 | 119.16 (15) | C11—C12—H12 | 119.9 |
C3—C4—C5 | 119.02 (16) | C14—C13—C12 | 119.92 (14) |
C3—C4—H4 | 120.5 | C14—C13—H13 | 120.0 |
C5—C4—H4 | 120.5 | C12—C13—H13 | 120.0 |
C6—C5—C4 | 121.15 (17) | C13—C14—C15 | 120.11 (14) |
C6—C5—H5 | 119.4 | C13—C14—H14 | 119.9 |
C4—C5—H5 | 119.4 | C15—C14—H14 | 119.9 |
C1—C6—C5 | 118.10 (14) | C10—C15—C14 | 120.35 (15) |
C1—C6—C7 | 120.59 (13) | C10—C15—H15 | 119.8 |
C5—C6—C7 | 121.30 (15) | C14—C15—H15 | 119.8 |
C6—C7—C8 | 111.85 (12) | N1—C16—C9 | 175.67 (15) |
C6—C7—H7A | 109.2 | N2—C17—C9 | 112.33 (11) |
C8—C7—H7A | 109.2 | N2—C17—H17A | 109.1 |
C6—C7—H7B | 109.2 | C9—C17—H17A | 109.1 |
C8—C7—H7B | 109.2 | N2—C17—H17B | 109.1 |
H7A—C7—H7B | 107.9 | C9—C17—H17B | 109.1 |
C7—C8—C9 | 114.21 (11) | H17A—C17—H17B | 107.9 |
C7—C8—H8A | 108.7 | N3—C18—N4 | 115.46 (16) |
C9—C8—H8A | 108.7 | N3—C18—H18 | 122.3 |
C7—C8—H8B | 108.7 | N4—C18—H18 | 122.3 |
C9—C8—H8B | 108.7 | N4—C19—N2 | 110.83 (15) |
H8A—C8—H8B | 107.6 | N4—C19—H19 | 124.6 |
C16—C9—C10 | 110.05 (11) | N2—C19—H19 | 124.6 |
C19—N2—N3—C18 | −0.44 (17) | C16—C9—C10—C11 | −159.29 (13) |
C17—N2—N3—C18 | −171.49 (14) | C8—C9—C10—C11 | −39.62 (17) |
C6—C1—C2—C3 | −1.1 (3) | C17—C9—C10—C11 | 80.90 (15) |
C1—C2—C3—C4 | −0.2 (3) | C15—C10—C11—C12 | −0.5 (2) |
C1—C2—C3—Cl1 | 179.73 (13) | C9—C10—C11—C12 | −174.29 (13) |
C2—C3—C4—C5 | 1.0 (3) | C10—C11—C12—C13 | 0.5 (2) |
Cl1—C3—C4—C5 | −178.99 (14) | C11—C12—C13—C14 | 0.1 (2) |
C3—C4—C5—C6 | −0.4 (3) | C12—C13—C14—C15 | −0.6 (2) |
C2—C1—C6—C5 | 1.5 (2) | C11—C10—C15—C14 | 0.0 (2) |
C2—C1—C6—C7 | −179.47 (15) | C9—C10—C15—C14 | 173.75 (13) |
C4—C5—C6—C1 | −0.8 (2) | C13—C14—C15—C10 | 0.5 (2) |
C4—C5—C6—C7 | −179.76 (15) | C19—N2—C17—C9 | −94.71 (18) |
C1—C6—C7—C8 | −77.25 (17) | N3—N2—C17—C9 | 74.23 (16) |
C5—C6—C7—C8 | 101.70 (17) | C16—C9—C17—N2 | −65.98 (14) |
C6—C7—C8—C9 | 174.47 (12) | C10—C9—C17—N2 | 54.17 (16) |
C7—C8—C9—C16 | 60.28 (15) | C8—C9—C17—N2 | 178.56 (11) |
C7—C8—C9—C10 | −61.39 (16) | N2—N3—C18—N4 | 0.2 (2) |
C7—C8—C9—C17 | 177.73 (12) | C19—N4—C18—N3 | 0.0 (2) |
C16—C9—C10—C15 | 27.07 (17) | C18—N4—C19—N2 | −0.34 (19) |
C8—C9—C10—C15 | 146.73 (13) | N3—N2—C19—N4 | 0.52 (18) |
C17—C9—C10—C15 | −92.74 (15) | C17—N2—C19—N4 | 170.36 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N1i | 0.99 | 2.53 | 3.522 (2) | 178 |
C11—H11···N1i | 0.95 | 2.60 | 3.533 (2) | 166 |
C17—H17A···N1ii | 0.99 | 2.58 | 3.5101 (18) | 156 |
C18—H18···N4iii | 0.95 | 2.46 | 3.277 (2) | 144 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+2; (iii) −x+3/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N1i | 0.99 | 2.53 | 3.522 (2) | 178 |
C11—H11···N1i | 0.95 | 2.60 | 3.533 (2) | 166 |
C17—H17A···N1ii | 0.99 | 2.58 | 3.5101 (18) | 156 |
C18—H18···N4iii | 0.95 | 2.46 | 3.277 (2) | 144 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+2; (iii) −x+3/2, y+1/2, −z+3/2. |
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).
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Fenbuconazole, [systematic name: (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile], is a conazole fungicide and it has been used for the control of leaf spot, yellow and brown rust, powdery mildew, and net blotch on various agricultural and horticultural crops (Li et al., 2012). However, until now its crystal structure has not been reported. The dihedral angles between the planes of the central benzene and the terminal chlorophenyl and triazole rings are 32.77 (5) and 32.97 (5)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Rizzoli et al., 2009; Yin et al., 2014).
In the crystal structure (Fig. 2), C—H··· N hydrogen bonds and weak C3–Cl1···Cg1iv (Cg1 is the centroid of the N2–N3–C18–N4–C19 ring) interaction [3.7892 (9) Å] with a chlorophenyl ring are observed (Table 1), forming two-dimensional networks parelle to (101) plane. In addition, the planes are linked by weak intermolecular π···π interaction between the terminal chlorophenyl ring systems [Cg2···Cg2v, 3.8597 (9) Å], resulting in a three-dimensional architecture. (Cg2 is the centroid of the C1–C6 ring) [for symmetry codes: (iv), -x + 1, -y + 1, -z + 2, (v), -x, -y + 1, -z + 2].