{4-[(2,4-Dichloro­benzo­yloxy)meth­yl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichloro­benzoate

Ismatov, D.; Azizov, U.; Talipov, S.; Ashurov, J.

doi:10.1107/S1600536811035550

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2590

https://doi.org/10.1107/S1600536811035550

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{4-[(2,4-Dichlorobenzoyloxy)methyl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate

Dilmurot Ismatov,^a ^* Umarkhon Azizov,^b Samat Talipov ^c and Jamshid Ashurov ^c

^aTashkent Chemical Technology Institute, A. Navoyi, 11, Tashkent, Uzbekistan, ^bUzbekistan Scientific Research Pharmacological Chemistry Institute (named after A. Sultonov), Durmon yuli, 40, Uzbekistan, and ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str. 83, Tashkent, 100125 Uzbekistan
^*Correspondence e-mail: x-ray.uz@mail.ru

(Received 3 August 2011; accepted 31 August 2011; online 14 September 2011)

In the title molecule, C₂₄H₁₅Cl₄N₃O₄, the triazole ring makes dihedral angles of 72.02 (12), 81.60 (12) and 73.82 (11)°, respectively, with the adjacent phenyl ring and the two dichlorobenzene rings. In the crystal, a weak C—H⋯N interaction, a short Cl⋯Cl contact [3.307 (2) Å] and a π–π stacking interaction [centroid–centroid distance = 3.568 (4) Å] are observed. An intramolecular C—H⋯O interaction is also present.

Related literature

For the pharmacological activities of 1,2,3-triazole derivatives, see: Dzhuraev et al. (1990 ); Karimkulov et al. (1991 ); Zakirov et al. (2001 ). For a related structure, see: Jin et al. (2004 ).

Experimental

Crystal data

C₂₄H₁₅Cl₄N₃O₄
M_r = 551.19
Monoclinic, P 2₁ /n
a = 8.908 (5) Å
b = 19.567 (5) Å
c = 13.908 (5) Å
β = 104.010 (5)°
V = 2352.1 (17) Å³
Z = 4
Cu Kα radiation
μ = 4.91 mm⁻¹
T = 293 K
0.6 × 0.4 × 0.3 mm

Data collection

Oxford Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.050, T_max = 0.229
20081 measured reflections
4196 independent reflections
3370 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.02
4196 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O4	0.97	2.49	3.280 (3)	139
C9—H9⋯N2ⁱ	0.93	2.58	3.288 (3)	134
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035550/is2762sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035550/is2762Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035550/is2762Isup3.cml

checkCIF report

Comment top

In last few decades, much attention has been paid to the synthesis of 1,2,3-triazole systems mainly due to their broad spectrum of pharmacological properties. 1,2,3-Triazole derivatives possess variety of pharmacological activities such as anti inflammatory, antiviral and antibacterial (Dzhuraev et al., 1990; Karimkulov et al., 1991; Zakirov et al., 2001).

In the title compound, {4-[(2,4-dichlorobenzoyloxy)methyl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate, C₂₄H₁₅N₃O₄Cl₄, the triazole ring (N1/N2/N3/C4/C5) is ideal planar with a greatest deviation of 0.0037 (12) Å (atom N3) from the mean plane and the benzyl rings of dichlorobenzoyloxy substituents (C8–C13 and C16–C21) are tilted out of this plane at 81.60 (12) and 73.82 (11)°, respectively. The dihedral angles between these benzyl rings and corresponding carboxylic fragments (O1/C7/O2 and O3/C15/O4) are 5.9 (4) and 26.9 (3)°, respectively. The dihedral angle between the triazole and phenyl (C22–C27) rings is 72.02 (12)°. The C5—N1 and C4—N2 bond lengths in the triazole ring are 1.352 (3) and 1.361 (3) Å, respectively. The values of these distances are shorter than the pertinent single bond length of 1.443 Å and are longer than the double bond length of 1.269 Å (Jin et al., 2004).

An intermolecular Cl1···Cl1 (-x, 1 - y, 2 - z) contact and a π–π stacking interaction with a Cg1···Cg2 (x - 1/2, 1/2 - y, z + 1/2) distance of 3.568 (4) Å stabilize the crystal structure; Cg1 and Cg2 are the centroids of the C8–C13 and C16–C21 rings, respectively.

Related literature top

For the pharmacological activities of 1,2,3-triazole derivatives, see: Dzhuraev et al. (1990); Karimkulov et al. (1991); Zakirov et al. (2001). For a related structure, see: Jin et al. (2004).

Experimental top

As a result of etherification 24.6 g (0.13 mole) of 2,4-dichlorbenzoic acid with 5.54 g (0.07 mole) of 2-butendiole-1, 4 refluxing for 2 h in benzene containing sulfuric acid as catalyst was got of 1,4-bis-(2,4-dichlorbenzoyloxy)-butene-2 [yield 22.55 g (82.2%), m.p. 364–365 K]. The reaction of obtaining bis-ester with 6.8 g (0.57 mole) phenylazide in 100 ml of toluene was carrying out within 7 h. Then the reaction mixture was cooled. The precipitate [1-phenyl-4,5-bis-(dichlorobenzoyloxymethyl)-1,2,3-triazole, yield 27.84 g (96.8%)] was collected by filtration and purified by recrystallization from ethanol (m.p. 383–384 K).

Structure description top

For the pharmacological activities of 1,2,3-triazole derivatives, see: Dzhuraev et al. (1990); Karimkulov et al. (1991); Zakirov et al. (2001). For a related structure, see: Jin et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme.
	Fig. 2. A packing diagram for the title compound. Dashed lines indicated C—H···N interactions.

{4-[(2,4-Dichlorobenzoyloxy)methyl]-1-phenyl-1H- 1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate top

Crystal data top

C₂₄H₁₅Cl₄N₃O₄	F(000) = 1120
M_r = 551.19	D_x = 1.557 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6999 reflections
a = 8.908 (5) Å	θ = 3.3–67.0°
b = 19.567 (5) Å	µ = 4.91 mm⁻¹
c = 13.908 (5) Å	T = 293 K
β = 104.010 (5)°	Prismatic, colourless
V = 2352.1 (17) Å³	0.6 × 0.4 × 0.3 mm
Z = 4

Data collection top

Oxford Xcalibur Ruby diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.2576 pixels mm^-1	θ_max = 66.9°, θ_min = 4.0°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −23→23
T_min = 0.050, T_max = 0.229	l = −16→16
20081 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0642P)² + 0.6051P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4196 reflections	Δρ_max = 0.28 e Å⁻³
317 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00144 (16)

Crystal data top

C₂₄H₁₅Cl₄N₃O₄	V = 2352.1 (17) Å³
M_r = 551.19	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 8.908 (5) Å	µ = 4.91 mm⁻¹
b = 19.567 (5) Å	T = 293 K
c = 13.908 (5) Å	0.6 × 0.4 × 0.3 mm
β = 104.010 (5)°

Data collection top

Oxford Xcalibur Ruby diffractometer	4196 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3370 reflections with I > 2σ(I)
T_min = 0.050, T_max = 0.229	R_int = 0.035
20081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
4196 reflections	Δρ_min = −0.33 e Å⁻³
317 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.

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	0.10801 (9)	0.46153 (5)	0.93488 (6)	0.0854 (3)
Cl2	0.19070 (9)	0.22022 (3)	0.77880 (5)	0.0670 (2)
Cl3	1.25569 (8)	0.07713 (3)	0.26450 (5)	0.0597 (2)
Cl4	1.01206 (10)	0.09158 (3)	0.57671 (5)	0.0710 (2)
O1	0.44606 (18)	0.34288 (7)	0.59759 (11)	0.0417 (4)
O2	0.3595 (2)	0.24058 (8)	0.62934 (13)	0.0562 (4)
O3	0.98996 (17)	0.31279 (8)	0.52445 (12)	0.0459 (4)
O4	0.8516 (2)	0.22445 (9)	0.55843 (14)	0.0592 (5)
N1	0.52546 (19)	0.39978 (8)	0.40630 (12)	0.0363 (4)
N2	0.6236 (2)	0.44090 (10)	0.37294 (15)	0.0471 (5)
N3	0.7620 (2)	0.42975 (9)	0.42858 (15)	0.0470 (5)
C4	0.7548 (2)	0.38112 (10)	0.49722 (15)	0.0391 (5)
C5	0.6030 (2)	0.36183 (10)	0.48375 (14)	0.0354 (4)
C6	0.5258 (3)	0.30865 (10)	0.53193 (16)	0.0404 (5)
H6A	0.4526	0.2829	0.4820	0.048*
H6B	0.6021	0.2772	0.5692	0.048*
C7	0.3658 (2)	0.30065 (10)	0.64358 (14)	0.0342 (4)
C8	0.2928 (2)	0.33971 (10)	0.71267 (14)	0.0344 (4)
C9	0.3061 (3)	0.41067 (11)	0.71796 (17)	0.0430 (5)
H9	0.3562	0.4331	0.6757	0.052*
C10	0.2474 (3)	0.44875 (13)	0.78378 (18)	0.0523 (6)
H10	0.2567	0.4961	0.7855	0.063*
C11	0.1748 (3)	0.41542 (14)	0.84679 (17)	0.0529 (6)
C12	0.1561 (3)	0.34554 (15)	0.84364 (17)	0.0525 (6)
H12	0.1048	0.3238	0.8859	0.063*
C13	0.2148 (2)	0.30801 (12)	0.77651 (15)	0.0420 (5)
C14	0.8976 (3)	0.35859 (13)	0.56945 (18)	0.0502 (6)
H14B	0.9590	0.3983	0.5957	0.060*
H14A	0.8696	0.3354	0.6242	0.060*
C15	0.9516 (2)	0.24628 (11)	0.52285 (15)	0.0405 (5)
C16	1.0439 (2)	0.20499 (10)	0.46763 (15)	0.0364 (4)
C17	1.1026 (2)	0.23534 (11)	0.39367 (16)	0.0401 (5)
H17	1.0943	0.2824	0.3850	0.048*
C18	1.1725 (3)	0.19760 (11)	0.33304 (16)	0.0422 (5)
H18	1.2107	0.2188	0.2841	0.051*
C19	1.1847 (2)	0.12779 (11)	0.34625 (16)	0.0413 (5)
C20	1.1354 (3)	0.09624 (11)	0.42153 (17)	0.0460 (5)
H20	1.1486	0.0494	0.4316	0.055*
C21	1.0662 (3)	0.13477 (11)	0.48190 (16)	0.0421 (5)
C22	0.3629 (2)	0.40125 (10)	0.35910 (15)	0.0372 (5)
C23	0.2613 (3)	0.43117 (11)	0.40706 (18)	0.0468 (5)
H23	0.2967	0.4500	0.4699	0.056*
C24	0.1058 (3)	0.43268 (13)	0.3600 (2)	0.0605 (7)
H24	0.0357	0.4525	0.3914	0.073*
C25	0.0543 (3)	0.40524 (14)	0.2673 (3)	0.0658 (8)
H25	−0.0507	0.4062	0.2365	0.079*
C26	0.1570 (3)	0.37622 (14)	0.2194 (2)	0.0636 (7)
H26	0.1213	0.3583	0.1561	0.076*
C27	0.3123 (3)	0.37379 (12)	0.26507 (17)	0.0487 (5)
H27	0.3821	0.3540	0.2333	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0745 (5)	0.1223 (7)	0.0652 (4)	0.0175 (5)	0.0282 (4)	−0.0319 (4)
Cl2	0.0858 (5)	0.0543 (4)	0.0696 (4)	−0.0209 (3)	0.0358 (4)	0.0128 (3)
Cl3	0.0716 (4)	0.0545 (4)	0.0595 (4)	0.0131 (3)	0.0285 (3)	−0.0055 (3)
Cl4	0.1151 (6)	0.0443 (3)	0.0688 (4)	0.0069 (3)	0.0518 (4)	0.0151 (3)
O1	0.0529 (9)	0.0339 (7)	0.0469 (8)	−0.0018 (6)	0.0285 (7)	0.0012 (6)
O2	0.0788 (12)	0.0353 (8)	0.0641 (10)	−0.0067 (8)	0.0359 (9)	−0.0011 (7)
O3	0.0415 (9)	0.0389 (8)	0.0590 (9)	0.0030 (6)	0.0157 (7)	−0.0087 (7)
O4	0.0621 (11)	0.0522 (10)	0.0737 (11)	0.0043 (8)	0.0368 (10)	0.0067 (8)
N1	0.0382 (9)	0.0336 (9)	0.0429 (9)	0.0017 (7)	0.0210 (8)	0.0021 (7)
N2	0.0469 (11)	0.0420 (10)	0.0600 (12)	−0.0006 (8)	0.0275 (10)	0.0082 (9)
N3	0.0428 (11)	0.0422 (10)	0.0624 (12)	−0.0025 (8)	0.0251 (10)	0.0002 (9)
C4	0.0429 (12)	0.0335 (10)	0.0450 (11)	0.0019 (9)	0.0184 (9)	−0.0092 (9)
C5	0.0434 (12)	0.0314 (10)	0.0362 (10)	0.0045 (8)	0.0188 (9)	−0.0035 (8)
C6	0.0493 (13)	0.0344 (10)	0.0429 (11)	0.0042 (9)	0.0218 (10)	0.0024 (8)
C7	0.0343 (11)	0.0352 (11)	0.0325 (10)	−0.0021 (8)	0.0069 (8)	0.0056 (8)
C8	0.0314 (10)	0.0396 (10)	0.0319 (10)	0.0001 (8)	0.0069 (8)	0.0052 (8)
C9	0.0437 (12)	0.0412 (11)	0.0470 (12)	0.0023 (9)	0.0163 (10)	0.0047 (9)
C10	0.0534 (14)	0.0481 (13)	0.0569 (14)	0.0078 (11)	0.0165 (12)	−0.0056 (11)
C11	0.0427 (13)	0.0741 (17)	0.0420 (12)	0.0121 (12)	0.0104 (10)	−0.0107 (11)
C12	0.0432 (13)	0.0786 (18)	0.0386 (12)	0.0023 (12)	0.0157 (10)	0.0093 (11)
C13	0.0383 (12)	0.0498 (12)	0.0377 (11)	−0.0021 (10)	0.0091 (9)	0.0084 (9)
C14	0.0486 (13)	0.0458 (12)	0.0556 (13)	0.0046 (10)	0.0115 (11)	−0.0160 (10)
C15	0.0397 (12)	0.0409 (11)	0.0381 (10)	0.0043 (9)	0.0040 (9)	0.0019 (9)
C16	0.0339 (11)	0.0354 (10)	0.0382 (10)	0.0005 (8)	0.0052 (8)	−0.0002 (8)
C17	0.0420 (12)	0.0318 (10)	0.0451 (11)	0.0011 (9)	0.0080 (9)	0.0030 (8)
C18	0.0447 (12)	0.0400 (11)	0.0428 (11)	−0.0022 (9)	0.0125 (10)	0.0051 (9)
C19	0.0383 (11)	0.0419 (12)	0.0431 (11)	0.0047 (9)	0.0087 (9)	−0.0020 (9)
C20	0.0565 (14)	0.0310 (10)	0.0501 (12)	0.0049 (10)	0.0125 (11)	0.0030 (9)
C21	0.0484 (13)	0.0362 (11)	0.0421 (11)	−0.0007 (9)	0.0117 (10)	0.0044 (9)
C22	0.0417 (12)	0.0301 (10)	0.0443 (11)	0.0040 (8)	0.0195 (9)	0.0077 (8)
C23	0.0522 (14)	0.0414 (12)	0.0539 (13)	0.0083 (10)	0.0268 (11)	0.0052 (10)
C24	0.0488 (15)	0.0526 (14)	0.091 (2)	0.0154 (12)	0.0369 (15)	0.0208 (14)
C25	0.0443 (15)	0.0544 (15)	0.094 (2)	0.0035 (12)	0.0082 (14)	0.0240 (15)
C26	0.0657 (18)	0.0559 (15)	0.0608 (15)	−0.0032 (13)	−0.0010 (13)	0.0053 (12)
C27	0.0558 (14)	0.0444 (12)	0.0498 (13)	0.0041 (11)	0.0202 (11)	0.0017 (10)

Geometric parameters (Å, º) top

Cl1—C11	1.738 (2)	C11—C12	1.377 (4)
Cl2—C13	1.733 (2)	C12—C13	1.386 (3)
Cl3—C19	1.739 (2)	C12—H12	0.9300
Cl4—C21	1.730 (2)	C14—H14B	0.9700
O1—C7	1.351 (2)	C14—H14A	0.9700
O1—C6	1.449 (2)	C15—C16	1.491 (3)
O2—C7	1.191 (3)	C16—C17	1.395 (3)
O3—C15	1.344 (3)	C16—C21	1.396 (3)
O3—C14	1.457 (3)	C17—C18	1.378 (3)
O4—C15	1.198 (3)	C17—H17	0.9300
N1—N2	1.350 (2)	C18—C19	1.379 (3)
N1—C5	1.352 (3)	C18—H18	0.9300
N1—C22	1.438 (3)	C19—C20	1.376 (3)
N2—N3	1.306 (3)	C20—C21	1.380 (3)
N3—C4	1.360 (3)	C20—H20	0.9300
C4—C5	1.373 (3)	C22—C23	1.378 (3)
C4—C14	1.484 (3)	C22—C27	1.384 (3)
C5—C6	1.492 (3)	C23—C24	1.382 (4)
C6—H6A	0.9700	C23—H23	0.9300
C6—H6B	0.9700	C24—C25	1.368 (4)
C7—C8	1.494 (3)	C24—H24	0.9300
C8—C9	1.394 (3)	C25—C26	1.378 (4)
C8—C13	1.398 (3)	C25—H25	0.9300
C9—C10	1.378 (3)	C26—C27	1.376 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.373 (4)	C27—H27	0.9300
C10—H10	0.9300

C7—O1—C6	114.32 (15)	O3—C14—H14A	109.2
C15—O3—C14	115.79 (18)	C4—C14—H14A	109.2
N2—N1—C5	110.66 (17)	H14B—C14—H14A	107.9
N2—N1—C22	119.68 (17)	O4—C15—O3	123.4 (2)
C5—N1—C22	129.66 (17)	O4—C15—C16	125.3 (2)
N3—N2—N1	107.09 (17)	O3—C15—C16	111.32 (18)
N2—N3—C4	109.52 (18)	C17—C16—C21	117.27 (19)
N3—C4—C5	108.01 (19)	C17—C16—C15	120.06 (18)
N3—C4—C14	120.3 (2)	C21—C16—C15	122.52 (19)
C5—C4—C14	131.7 (2)	C18—C17—C16	121.93 (19)
N1—C5—C4	104.71 (18)	C18—C17—H17	119.0
N1—C5—C6	122.59 (19)	C16—C17—H17	119.0
C4—C5—C6	132.6 (2)	C17—C18—C19	118.8 (2)
O1—C6—C5	108.05 (16)	C17—C18—H18	120.6
O1—C6—H6A	110.1	C19—C18—H18	120.6
C5—C6—H6A	110.1	C20—C19—C18	121.1 (2)
O1—C6—H6B	110.1	C20—C19—Cl3	118.39 (17)
C5—C6—H6B	110.1	C18—C19—Cl3	120.48 (17)
H6A—C6—H6B	108.4	C19—C20—C21	119.3 (2)
O2—C7—O1	122.27 (18)	C19—C20—H20	120.3
O2—C7—C8	126.98 (18)	C21—C20—H20	120.3
O1—C7—C8	110.74 (16)	C20—C21—C16	121.4 (2)
C9—C8—C13	117.22 (19)	C20—C21—Cl4	116.42 (16)
C9—C8—C7	119.93 (18)	C16—C21—Cl4	122.19 (17)
C13—C8—C7	122.81 (19)	C23—C22—C27	121.4 (2)
C10—C9—C8	122.2 (2)	C23—C22—N1	119.6 (2)
C10—C9—H9	118.9	C27—C22—N1	119.02 (18)
C8—C9—H9	118.9	C22—C23—C24	118.7 (2)
C11—C10—C9	118.7 (2)	C22—C23—H23	120.7
C11—C10—H10	120.6	C24—C23—H23	120.7
C9—C10—H10	120.6	C25—C24—C23	120.5 (2)
C10—C11—C12	121.6 (2)	C25—C24—H24	119.8
C10—C11—Cl1	119.8 (2)	C23—C24—H24	119.8
C12—C11—Cl1	118.6 (2)	C24—C25—C26	120.4 (3)
C11—C12—C13	119.0 (2)	C24—C25—H25	119.8
C11—C12—H12	120.5	C26—C25—H25	119.8
C13—C12—H12	120.5	C27—C26—C25	120.1 (3)
C12—C13—C8	121.3 (2)	C27—C26—H26	119.9
C12—C13—Cl2	116.37 (17)	C25—C26—H26	119.9
C8—C13—Cl2	122.32 (17)	C26—C27—C22	118.9 (2)
O3—C14—C4	111.88 (18)	C26—C27—H27	120.5
O3—C14—H14B	109.2	C22—C27—H27	120.5
C4—C14—H14B	109.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O4	0.97	2.49	3.280 (3)	139
C9—H9···N2ⁱ	0.93	2.58	3.288 (3)	134

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅Cl₄N₃O₄
M_r	551.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.908 (5), 19.567 (5), 13.908 (5)
β (°)	104.010 (5)
V (Å³)	2352.1 (17)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.91
Crystal size (mm)	0.6 × 0.4 × 0.3

Data collection
Diffractometer	Oxford Xcalibur Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.050, 0.229
No. of measured, independent and observed [I > 2σ(I)] reflections	20081, 4196, 3370
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.02
No. of reflections	4196
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.33

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O4	0.97	2.49	3.280 (3)	138.8
C9—H9···N2ⁱ	0.93	2.58	3.288 (3)	133.8

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (grant No. FA-F3-T-141).

References

Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dzhuraev, A. D., Makhsumov, A. G., Zakirov, U. B., Nikbaev, A. G. & Karimkulov, K. M. (1990). Khim. Farm. Zh. 24 30–31. CAS Google Scholar
Jin, Z.-M., Li, L., Li, M.-C., Hu, M.-L. & Shen, L. (2004). Acta Cryst. C60, o642–o643. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Karimkulov, K. M., Dzhuraev, A. D., Makhsumov, A. G. & Amanov, N. (1991). Khim. Farm. Zh. 25, 40–41. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zakirov, A. U., Pulatov, Kh. Kh., Ismatov, D. N. & Azizov, U. M. (2001). Eksp. Klin. Farmakoter. 64, 50–52. CAS Google Scholar

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

{4-[(2,4-Di­chloro­benzo­yl­oxy)meth­yl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-di­chloro­benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{4-[(2,4-Dichlorobenzoyloxy)methyl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate