Ethyl 4-{[1-(2,4-dichloro­benz­yl)-1H-1,2,3-triazol-4-yl]meth­oxy}-8-(trifluoro­meth­yl)quinoline-3-carboxyl­ate

Fun, H.-K.; Ooi, C.W.; Garudachari, B.; Isloor, A.M.; Rashid, S.A.

doi:10.1107/S1600536812039633

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o3017-o3018

https://doi.org/10.1107/S1600536812039633

Open

access

Ethyl 4-{[1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}-8-(trifluoromethyl)quinoline-3-carboxylate

Hoong-Kun Fun,^a,^b ^*‡ Chin Wei Ooi,^a § B. Garudachari,^c Arun M. Isloor ^c and Suraya A. Rashid ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^cMedicinal Chemistry Laboratory, Department of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Chemical and Environmental Engineering, Faculty of Engineering, Universiti Putra Malaysia, 43400 UPM SERDANG, Selangor, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 September 2012; accepted 18 September 2012; online 26 September 2012)

In the title compound, C₂₃H₁₇Cl₂F₃N₄O₃, the triazole ring makes dihedral angles of 50.27 (6) and 82.78 (7)° with the quinoline ring system and the dichloro-substituted benzene ring. The dihedral angle between the quinoline and dichloro-substituted benzene rings is 38.17 (4)°. In the crystal, molecules are linked via C—H⋯N, C—H⋯F and C—H⋯O hydrogen bonds into a three-dimensional network. The crystal is further consolidated by C—H⋯π contacts to the triazole ring and inversion-related π–π interactions between the benzene and pyridine rings of quinoline systems [centroid–centroid distance = 3.7037 (7) Å].

Related literature

For background and the biological activity of quinoline derivatives, see: Bi et al. (2004 ); He et al. (2005 ); Holla et al. (2006 ); Isloor et al. (2000 , 2009 ); Vijesh et al. (2010 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₁₇Cl₂F₃N₄O₃
M_r = 525.31
Monoclinic, P 2₁ /c
a = 10.0414 (6) Å
b = 18.3997 (11) Å
c = 15.5456 (7) Å
β = 128.559 (2)°
V = 2246.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 100 K
0.32 × 0.31 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.896, T_max = 0.942
28920 measured reflections
8173 independent reflections
6633 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.102
S = 1.03
8173 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N3ⁱ	0.93	2.62	3.3330 (14)	134
C7—H7A⋯F1ⁱⁱ	0.97	2.46	3.1712 (15)	130
C8—H8A⋯O2ⁱⁱⁱ	0.93	2.25	3.0183 (18)	139
C2—H2A⋯Cg1^iv	0.93	2.92	3.8418 (17)	173
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+2; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039633/sj5262sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039633/sj5262Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039633/sj5262Isup3.cml

checkCIF report

Comment top

Quinoline and its derivatives play an important role in medicinal chemistry research. Fluorinated quinolines, in particular CF₃ substituted quinolines, occupy a significant place in modern medicinal chemistry. Biological studies clearly indicated that the presence of trifluoromethyl group in positions 7 and 8 of the quinoline ring is responsible for the biological activity (Holla et al., 2006; He et al., 2005; Bi et al., 2004). On the other hand, heterocyclic compounds play an important role in an untiring effort aimed at developing new antimicrobial agents with a new mechanism of action. These heterocyclic compounds are well known to possess diverse pharmacological properties, viz. antibacterial, antifungal, anti-inflammatory, anticonvulsant, antiviral, antimalarial, antituberculosis, and anticancer effects (Isloor et al., 2000, 2009; Vijesh et al., 2010). In view of this biological importance, we have synthesized the title compound to study its crystal structure.

In the title compound (Fig. 1), the triazole (N1–N3/C8/C9) ring makes dihedral angles of 50.27 (6) and 82.78 (7)° with the quinoline ring system (N4/C11–C19) and the dichloro-substituted benzene ring (C1–C6) respectively. The dihedral angle between the quinoline and the dichloro-substituted benzene ring is 38.17 (4)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), the molecules linked via intermolecular C5—H5A···N3, C7—H7A···F1 and C8—H8A···O2 hydrogen bonds (Table 1) into a three dimensional network. The crystal is further consolidated by C2—H2A···Cg1 interactions (Table 1), involving the triazole ring (N1–N3/C8/C9). Weak π–π interactions are also observed with Cg2···Cg4 = 3.7037 (7) Å [symmetry code: -x, 1 - y, 2 - z], where Cg2 and Cg4 are centroids of the pyridine ring (N4/C11/C12/C17/C18/C19) and the benzene ring (C12–C17) respectively.

Related literature top

For background and the biological activity of quinoline derivatives, see: Bi et al. (2004); He et al. (2005); Holla et al. (2006); Isloor et al. (2000, 2009); Vijesh et al. (2010). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

To a stirred solution of 1-(bromomethyl)-2,4-dichlorobenzene (0.50 g, 0.0020 mol), sodium azide (0.149 g, 0.0022 mol) in aqueous polyethylene glycol (PEG 400) (10 ml, 1:1, v/v), ethyl 4-(prop-2-yn-1-yloxy)-8- (trifluoromethyl)quinoline-3-carboxylate (0.711 g, 0.0022 mol), sodium ascorbate (0.435 g, 0.0022 mol), 10 mol of copper iodide were added. The heterogeneous mixture was stirred vigorously overnight. Completion of the reaction was monitored by the TLC. The product was extracted in ethyl acetate and concentrated. The crude product was purified by column chromatography using pet ether and ethyl acetate as eluents. Crystals were grown by slow evaporation of a dilute ethanol solution at room temperature. Yield: 0.35 g, 32.11 %, M. p.: 423–425 K.

Structure description top

For background and the biological activity of quinoline derivatives, see: Bi et al. (2004); He et al. (2005); Holla et al. (2006); Isloor et al. (2000, 2009); Vijesh et al. (2010). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Ethyl 4-{[1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}-8- (trifluoromethyl)quinoline-3-carboxylate top

Crystal data top

C₂₃H₁₇Cl₂F₃N₄O₃	F(000) = 1072
M_r = 525.31	D_x = 1.554 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9559 reflections
a = 10.0414 (6) Å	θ = 2.3–32.6°
b = 18.3997 (11) Å	µ = 0.35 mm⁻¹
c = 15.5456 (7) Å	T = 100 K
β = 128.559 (2)°	Block, colourless
V = 2246.0 (2) Å³	0.32 × 0.31 × 0.17 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	8173 independent reflections
Radiation source: fine-focus sealed tube	6633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 32.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.896, T_max = 0.942	k = −26→27
28920 measured reflections	l = −23→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0562P)² + 0.415P] where P = (F_o² + 2F_c²)/3
8173 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₃H₁₇Cl₂F₃N₄O₃	V = 2246.0 (2) Å³
M_r = 525.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0414 (6) Å	µ = 0.35 mm⁻¹
b = 18.3997 (11) Å	T = 100 K
c = 15.5456 (7) Å	0.32 × 0.31 × 0.17 mm
β = 128.559 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	8173 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6633 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.942	R_int = 0.028
28920 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
8173 reflections	Δρ_min = −0.27 e Å⁻³
317 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.12680 (3)	0.821670 (15)	0.85096 (2)	0.02315 (7)
Cl2	−0.32434 (4)	0.689263 (18)	0.48063 (2)	0.02946 (7)
F1	−0.36101 (10)	0.45643 (4)	0.65715 (6)	0.02879 (16)
F2	−0.25813 (10)	0.52957 (5)	0.60326 (6)	0.03245 (17)
F3	−0.47656 (10)	0.56112 (5)	0.59016 (6)	0.03603 (19)
O1	0.32034 (9)	0.56730 (4)	1.13470 (6)	0.01678 (14)
O2	0.48813 (13)	0.39682 (6)	1.03651 (8)	0.0395 (3)
O3	0.55544 (11)	0.46603 (4)	1.17639 (7)	0.02473 (17)
N1	0.29130 (11)	0.78082 (5)	1.00429 (7)	0.01548 (15)
N2	0.30596 (12)	0.80120 (5)	1.09313 (7)	0.01942 (17)
N3	0.36803 (12)	0.74507 (5)	1.16052 (7)	0.01799 (16)
N4	0.01453 (12)	0.47968 (5)	0.81631 (7)	0.01919 (17)
C1	−0.07552 (13)	0.78849 (6)	0.77012 (8)	0.01699 (18)
C2	−0.20346 (13)	0.75504 (6)	0.67150 (9)	0.01960 (19)
H2A	−0.3127	0.7501	0.6499	0.024*
C3	−0.16378 (13)	0.72921 (6)	0.60602 (8)	0.01965 (19)
C4	−0.00095 (14)	0.73555 (6)	0.63755 (9)	0.02013 (19)
H4A	0.0239	0.7175	0.5931	0.024*
C5	0.12413 (13)	0.76941 (6)	0.73696 (8)	0.01918 (19)
H5A	0.2335	0.7739	0.7587	0.023*
C6	0.08973 (13)	0.79674 (5)	0.80482 (8)	0.01678 (17)
C7	0.22889 (13)	0.83146 (5)	0.91327 (8)	0.01838 (18)
H7A	0.3221	0.8454	0.9133	0.022*
H7B	0.1856	0.8750	0.9233	0.022*
C8	0.34385 (12)	0.71183 (5)	1.01398 (8)	0.01612 (17)
H8A	0.3464	0.6854	0.9640	0.019*
C9	0.39297 (12)	0.68906 (5)	1.11442 (8)	0.01461 (16)
C10	0.45857 (12)	0.61685 (5)	1.16863 (8)	0.01687 (18)
H10A	0.5263	0.5959	1.1500	0.020*
H10B	0.5318	0.6231	1.2478	0.020*
C11	0.22978 (12)	0.53905 (5)	1.03163 (8)	0.01451 (16)
C12	0.05997 (12)	0.56544 (5)	0.95288 (8)	0.01491 (17)
C13	−0.00764 (13)	0.62046 (5)	0.97944 (8)	0.01711 (18)
H13A	0.0597	0.6409	1.0494	0.021*
C14	−0.17216 (13)	0.64365 (5)	0.90227 (9)	0.01925 (19)
H14A	−0.2161	0.6797	0.9202	0.023*
C15	−0.27516 (14)	0.61315 (6)	0.79582 (9)	0.01969 (19)
H15A	−0.3863	0.6295	0.7439	0.024*
C16	−0.21298 (13)	0.55957 (5)	0.76808 (8)	0.01790 (18)
C17	−0.04291 (13)	0.53391 (5)	0.84626 (8)	0.01585 (17)
C18	0.17098 (14)	0.45736 (6)	0.89147 (9)	0.01910 (19)
H18A	0.2102	0.4206	0.8714	0.023*
C19	0.28671 (13)	0.48409 (5)	1.00108 (8)	0.01653 (17)
C20	0.45265 (14)	0.44489 (6)	1.07212 (9)	0.01967 (19)
C21	0.71534 (15)	0.42565 (6)	1.24926 (10)	0.0268 (2)
H21A	0.7758	0.4249	1.2192	0.032*
H21B	0.6929	0.3759	1.2575	0.032*
C22	0.81915 (19)	0.46389 (8)	1.35829 (12)	0.0428 (4)
H22A	0.9215	0.4368	1.4103	0.064*
H22B	0.7543	0.4676	1.3843	0.064*
H22C	0.8481	0.5117	1.3500	0.064*
C23	−0.32547 (15)	0.52651 (6)	0.65532 (9)	0.0236 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02094 (12)	0.02780 (13)	0.02435 (13)	0.00553 (9)	0.01591 (10)	0.00119 (9)
Cl2	0.02577 (13)	0.03967 (16)	0.02093 (13)	−0.01115 (11)	0.01358 (11)	−0.00591 (10)
F1	0.0312 (4)	0.0247 (3)	0.0217 (3)	−0.0053 (3)	0.0121 (3)	−0.0087 (3)
F2	0.0371 (4)	0.0409 (4)	0.0170 (3)	0.0021 (3)	0.0157 (3)	0.0006 (3)
F3	0.0250 (4)	0.0398 (4)	0.0187 (3)	0.0109 (3)	0.0015 (3)	−0.0020 (3)
O1	0.0178 (3)	0.0181 (3)	0.0134 (3)	−0.0053 (3)	0.0091 (3)	−0.0027 (2)
O2	0.0297 (5)	0.0477 (6)	0.0332 (5)	0.0175 (4)	0.0157 (4)	−0.0051 (4)
O3	0.0222 (4)	0.0196 (4)	0.0207 (4)	0.0056 (3)	0.0076 (3)	0.0040 (3)
N1	0.0157 (3)	0.0153 (4)	0.0159 (4)	−0.0003 (3)	0.0100 (3)	−0.0006 (3)
N2	0.0237 (4)	0.0178 (4)	0.0196 (4)	−0.0005 (3)	0.0149 (4)	−0.0022 (3)
N3	0.0205 (4)	0.0170 (4)	0.0184 (4)	−0.0016 (3)	0.0130 (3)	−0.0020 (3)
N4	0.0222 (4)	0.0165 (4)	0.0167 (4)	0.0015 (3)	0.0110 (3)	−0.0019 (3)
C1	0.0175 (4)	0.0174 (4)	0.0181 (4)	0.0041 (3)	0.0121 (4)	0.0048 (3)
C2	0.0152 (4)	0.0234 (5)	0.0197 (4)	0.0010 (3)	0.0106 (4)	0.0039 (4)
C3	0.0186 (4)	0.0213 (5)	0.0166 (4)	−0.0021 (3)	0.0098 (4)	0.0021 (3)
C4	0.0212 (5)	0.0234 (5)	0.0188 (4)	0.0014 (4)	0.0139 (4)	0.0029 (4)
C5	0.0163 (4)	0.0230 (5)	0.0193 (4)	0.0007 (3)	0.0117 (4)	0.0041 (4)
C6	0.0160 (4)	0.0161 (4)	0.0176 (4)	0.0019 (3)	0.0101 (4)	0.0042 (3)
C7	0.0185 (4)	0.0160 (4)	0.0194 (4)	−0.0003 (3)	0.0112 (4)	0.0030 (3)
C8	0.0164 (4)	0.0156 (4)	0.0160 (4)	0.0011 (3)	0.0099 (3)	−0.0009 (3)
C9	0.0129 (4)	0.0152 (4)	0.0143 (4)	−0.0024 (3)	0.0078 (3)	−0.0019 (3)
C10	0.0142 (4)	0.0165 (4)	0.0148 (4)	−0.0024 (3)	0.0066 (3)	−0.0003 (3)
C11	0.0170 (4)	0.0128 (4)	0.0134 (4)	−0.0018 (3)	0.0094 (3)	−0.0002 (3)
C12	0.0169 (4)	0.0123 (4)	0.0145 (4)	−0.0010 (3)	0.0092 (3)	−0.0005 (3)
C13	0.0191 (4)	0.0147 (4)	0.0179 (4)	−0.0025 (3)	0.0117 (4)	−0.0035 (3)
C14	0.0209 (5)	0.0145 (4)	0.0236 (5)	0.0003 (3)	0.0145 (4)	−0.0021 (3)
C15	0.0185 (4)	0.0167 (4)	0.0201 (5)	0.0019 (3)	0.0101 (4)	0.0013 (3)
C16	0.0187 (4)	0.0156 (4)	0.0142 (4)	0.0006 (3)	0.0077 (4)	−0.0001 (3)
C17	0.0185 (4)	0.0136 (4)	0.0144 (4)	−0.0001 (3)	0.0097 (3)	−0.0004 (3)
C18	0.0225 (5)	0.0159 (4)	0.0193 (4)	0.0011 (3)	0.0133 (4)	−0.0022 (3)
C19	0.0172 (4)	0.0149 (4)	0.0172 (4)	0.0006 (3)	0.0105 (4)	0.0009 (3)
C20	0.0189 (4)	0.0192 (4)	0.0215 (5)	0.0021 (3)	0.0129 (4)	0.0031 (3)
C21	0.0202 (5)	0.0219 (5)	0.0277 (5)	0.0048 (4)	0.0099 (4)	0.0102 (4)
C22	0.0331 (7)	0.0265 (6)	0.0304 (7)	0.0013 (5)	0.0009 (5)	0.0054 (5)
C23	0.0224 (5)	0.0242 (5)	0.0154 (4)	0.0035 (4)	0.0075 (4)	−0.0002 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7387 (11)	C7—H7B	0.9700
Cl2—C3	1.7383 (11)	C8—C9	1.3772 (14)
F1—C23	1.3429 (14)	C8—H8A	0.9300
F2—C23	1.3408 (15)	C9—C10	1.4891 (14)
F3—C23	1.3482 (13)	C10—H10A	0.9700
O1—C11	1.3594 (11)	C10—H10B	0.9700
O1—C10	1.4571 (12)	C11—C19	1.3833 (14)
O2—C20	1.2089 (14)	C11—C12	1.4282 (14)
O3—C20	1.3260 (14)	C12—C13	1.4161 (14)
O3—C21	1.4649 (13)	C12—C17	1.4201 (13)
N1—C8	1.3466 (13)	C13—C14	1.3711 (15)
N1—N2	1.3477 (12)	C13—H13A	0.9300
N1—C7	1.4689 (13)	C14—C15	1.4105 (15)
N2—N3	1.3186 (12)	C14—H14A	0.9300
N3—C9	1.3646 (13)	C15—C16	1.3724 (15)
N4—C18	1.3091 (14)	C15—H15A	0.9300
N4—C17	1.3710 (13)	C16—C17	1.4244 (14)
C1—C2	1.3873 (15)	C16—C23	1.5001 (15)
C1—C6	1.3970 (14)	C18—C19	1.4239 (14)
C2—C3	1.3878 (15)	C18—H18A	0.9300
C2—H2A	0.9300	C19—C20	1.4908 (14)
C3—C4	1.3886 (15)	C21—C22	1.5006 (19)
C4—C5	1.3908 (15)	C21—H21A	0.9700
C4—H4A	0.9300	C21—H21B	0.9700
C5—C6	1.3925 (15)	C22—H22A	0.9600
C5—H5A	0.9300	C22—H22B	0.9600
C6—C7	1.5054 (14)	C22—H22C	0.9600
C7—H7A	0.9700

C11—O1—C10	116.90 (8)	C19—C11—C12	118.84 (9)
C20—O3—C21	116.06 (9)	C13—C12—C17	120.01 (9)
C8—N1—N2	111.27 (8)	C13—C12—C11	121.76 (9)
C8—N1—C7	127.43 (9)	C17—C12—C11	118.21 (9)
N2—N1—C7	121.28 (8)	C14—C13—C12	120.17 (9)
N3—N2—N1	106.97 (8)	C14—C13—H13A	119.9
N2—N3—C9	108.95 (8)	C12—C13—H13A	119.9
C18—N4—C17	116.75 (9)	C13—C14—C15	120.34 (10)
C2—C1—C6	122.25 (10)	C13—C14—H14A	119.8
C2—C1—Cl1	117.85 (8)	C15—C14—H14A	119.8
C6—C1—Cl1	119.89 (8)	C16—C15—C14	120.67 (10)
C1—C2—C3	118.10 (10)	C16—C15—H15A	119.7
C1—C2—H2A	120.9	C14—C15—H15A	119.7
C3—C2—H2A	120.9	C15—C16—C17	120.55 (9)
C2—C3—C4	121.71 (10)	C15—C16—C23	119.98 (9)
C2—C3—Cl2	118.53 (8)	C17—C16—C23	119.45 (9)
C4—C3—Cl2	119.75 (9)	N4—C17—C12	122.67 (9)
C3—C4—C5	118.61 (10)	N4—C17—C16	119.07 (9)
C3—C4—H4A	120.7	C12—C17—C16	118.26 (9)
C5—C4—H4A	120.7	N4—C18—C19	126.15 (10)
C4—C5—C6	121.66 (10)	N4—C18—H18A	116.9
C4—C5—H5A	119.2	C19—C18—H18A	116.9
C6—C5—H5A	119.2	C11—C19—C18	117.37 (9)
C5—C6—C1	117.65 (9)	C11—C19—C20	127.57 (9)
C5—C6—C7	120.41 (9)	C18—C19—C20	114.90 (9)
C1—C6—C7	121.90 (10)	O2—C20—O3	123.18 (10)
N1—C7—C6	110.51 (8)	O2—C20—C19	121.81 (10)
N1—C7—H7A	109.5	O3—C20—C19	115.00 (9)
C6—C7—H7A	109.5	O3—C21—C22	106.89 (11)
N1—C7—H7B	109.5	O3—C21—H21A	110.3
C6—C7—H7B	109.5	C22—C21—H21A	110.3
H7A—C7—H7B	108.1	O3—C21—H21B	110.3
N1—C8—C9	104.60 (9)	C22—C21—H21B	110.3
N1—C8—H8A	127.7	H21A—C21—H21B	108.6
C9—C8—H8A	127.7	C21—C22—H22A	109.5
N3—C9—C8	108.21 (9)	C21—C22—H22B	109.5
N3—C9—C10	122.53 (9)	H22A—C22—H22B	109.5
C8—C9—C10	129.24 (9)	C21—C22—H22C	109.5
O1—C10—C9	111.58 (8)	H22A—C22—H22C	109.5
O1—C10—H10A	109.3	H22B—C22—H22C	109.5
C9—C10—H10A	109.3	F2—C23—F1	107.08 (9)
O1—C10—H10B	109.3	F2—C23—F3	106.34 (9)
C9—C10—H10B	109.3	F1—C23—F3	106.27 (10)
H10A—C10—H10B	108.0	F2—C23—C16	113.11 (10)
O1—C11—C19	124.63 (9)	F1—C23—C16	112.41 (9)
O1—C11—C12	116.38 (9)	F3—C23—C16	111.19 (9)

C8—N1—N2—N3	−0.11 (11)	C11—C12—C13—C14	−178.94 (10)
C7—N1—N2—N3	−178.65 (9)	C12—C13—C14—C15	−0.22 (16)
N1—N2—N3—C9	0.08 (11)	C13—C14—C15—C16	0.47 (17)
C6—C1—C2—C3	−0.03 (15)	C14—C15—C16—C17	−0.20 (17)
Cl1—C1—C2—C3	179.26 (8)	C14—C15—C16—C23	178.60 (10)
C1—C2—C3—C4	0.65 (16)	C18—N4—C17—C12	0.28 (15)
C1—C2—C3—Cl2	−178.39 (8)	C18—N4—C17—C16	−179.17 (10)
C2—C3—C4—C5	−0.66 (16)	C13—C12—C17—N4	−178.92 (10)
Cl2—C3—C4—C5	178.36 (8)	C11—C12—C17—N4	−0.22 (15)
C3—C4—C5—C6	0.05 (16)	C13—C12—C17—C16	0.53 (15)
C4—C5—C6—C1	0.53 (15)	C11—C12—C17—C16	179.23 (9)
C4—C5—C6—C7	178.48 (9)	C15—C16—C17—N4	179.18 (10)
C2—C1—C6—C5	−0.54 (15)	C23—C16—C17—N4	0.38 (15)
Cl1—C1—C6—C5	−179.82 (8)	C15—C16—C17—C12	−0.29 (15)
C2—C1—C6—C7	−178.46 (9)	C23—C16—C17—C12	−179.10 (10)
Cl1—C1—C6—C7	2.27 (13)	C17—N4—C18—C19	−0.02 (17)
C8—N1—C7—C6	51.57 (13)	O1—C11—C19—C18	175.75 (9)
N2—N1—C7—C6	−130.14 (10)	C12—C11—C19—C18	0.33 (14)
C5—C6—C7—N1	−101.78 (11)	O1—C11—C19—C20	0.67 (17)
C1—C6—C7—N1	76.08 (12)	C12—C11—C19—C20	−174.75 (10)
N2—N1—C8—C9	0.08 (11)	N4—C18—C19—C11	−0.28 (17)
C7—N1—C8—C9	178.52 (9)	N4—C18—C19—C20	175.42 (10)
N2—N3—C9—C8	−0.03 (11)	C21—O3—C20—O2	−2.25 (17)
N2—N3—C9—C10	−178.60 (9)	C21—O3—C20—C19	176.76 (9)
N1—C8—C9—N3	−0.03 (11)	C11—C19—C20—O2	179.10 (12)
N1—C8—C9—C10	178.41 (9)	C18—C19—C20—O2	3.91 (16)
C11—O1—C10—C9	74.10 (11)	C11—C19—C20—O3	0.08 (16)
N3—C9—C10—O1	91.43 (11)	C18—C19—C20—O3	−175.10 (9)
C8—C9—C10—O1	−86.82 (13)	C20—O3—C21—C22	173.46 (11)
C10—O1—C11—C19	75.83 (12)	C15—C16—C23—F2	125.51 (11)
C10—O1—C11—C12	−108.65 (10)	C17—C16—C23—F2	−55.68 (13)
O1—C11—C12—C13	2.78 (14)	C15—C16—C23—F1	−113.06 (11)
C19—C11—C12—C13	178.58 (9)	C17—C16—C23—F1	65.75 (14)
O1—C11—C12—C17	−175.90 (8)	C15—C16—C23—F3	5.93 (16)
C19—C11—C12—C17	−0.10 (14)	C17—C16—C23—F3	−175.25 (10)
C17—C12—C13—C14	−0.28 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N3ⁱ	0.93	2.62	3.3330 (14)	134
C7—H7A···F1ⁱⁱ	0.97	2.46	3.1712 (15)	130
C8—H8A···O2ⁱⁱⁱ	0.93	2.25	3.0183 (18)	139
C2—H2A···Cg1^iv	0.93	2.92	3.8418 (17)	173

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) x−1, −y+1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇Cl₂F₃N₄O₃
M_r	525.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.0414 (6), 18.3997 (11), 15.5456 (7)
β (°)	128.559 (2)
V (Å³)	2246.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.32 × 0.31 × 0.17

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.896, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	28920, 8173, 6633
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 1.03
No. of reflections	8173
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N3ⁱ	0.93	2.62	3.3330 (14)	134.3
C7—H7A···F1ⁱⁱ	0.9700	2.4600	3.1712 (15)	130.00
C8—H8A···O2ⁱⁱⁱ	0.9300	2.2500	3.0183 (18)	139.00
C2—H2A···Cg1^iv	0.9300	2.92	3.8418 (17)	173

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) x−1, −y+1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: F-8809-2012.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for a Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bi, Y., Stoy, P., Adam, L., He, B., Krupinski, J., Normandin, D., Pongrac, R., Seliger, L., Watson, A. & Macora, J. E. (2004). Bioorg. Med. Chem. Lett. 14, 1577–1580. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
He, J., Yan, L., Yang, R., Xiao, Z., Cheng, J., Zhou, W. & Zhang, Y. (2005). Bioorg. Med. Chem. Lett. 15, 2980–2985. Web of Science CrossRef PubMed CAS Google Scholar
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akbarali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040–2047. Web of Science CrossRef PubMed CAS Google Scholar
Isloor, A. M., Kalluraya, B. & Rao, M. (2000). J. Saudi Chem. Soc. 4, 265–270. CAS Google Scholar
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784–3787. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vijesh, A. M., Isloor, A. M., Prabhu, V., Ahmad, S. & Malladi, S. (2010). Eur. J. Med. Chem. 45, 5460–5464. Web of Science CrossRef CAS PubMed 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o3017-o3018

https://doi.org/10.1107/S1600536812039633

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 4-{[1-(2,4-di­chloro­benz­yl)-1H-1,2,3-triazol-4-yl]meth­­oxy}-8-(tri­fluoro­meth­yl)quinoline-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Ethyl 4-{[1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}-8-(trifluoromethyl)quinoline-3-carboxylate