Ethyl 4-({1-[2-(4-bromo-phen-yl)-2-oxo-eth-yl]-1H-1,2,3-triazol-4-yl}meth-oxy)-8-(trifluoro-meth-yl)quinoline-3-carboxyl-ate.

The title compound, C24H18BrF3N4O4, is a 1,2,3-triazole derivative featuring, among others, a quinoline-derived substituent. In the crystal, C-H⋯O, C-H⋯N and C-H⋯F contacts connect the mol-ecules into a three-dimensional network. The shortest centroid-centroid distance between two aromatic systems is 3.896 (2) Å and is found between the two different six-membered rings of the quinoline scaffold in neighbouring mol-ecules.

Related literature

For background to the industrial importance of heterocyclic compounds, see: Isloor et al. (2009 ▶); Vijesh et al. (2011 ▶); Ruanwasa et al. (2010 ▶). For pharmacological properties of quinoline-derived compounds, see: Chen et al. (2004 ▶); Kaur et al. (2010 ▶); Bekhit et al. (2004 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H18BrF3N4O4

M = 563.33

Monoclinic,

a = 5.2809 (2) Å

b = 24.5131 (10) Å

c = 18.3517 (7) Å

β = 99.643 (1)°

V = 2342.08 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 200 K

0.58 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.417, T max = 0.889

22440 measured reflections

5775 independent reflections

3774 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.141

S = 1.02

5775 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.93 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046417/im2409sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046417/im2409Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046417/im2409Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046417/im2409Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H18BrF3N4O4	F(000) = 1136
Mr = 563.33	Dx = 1.598 Mg m−3
Monoclinic, P21/c	Melting point = 380–378 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.2809 (2) Å	Cell parameters from 6880 reflections
b = 24.5131 (10) Å	θ = 2.4–27.9°
c = 18.3517 (7) Å	µ = 1.82 mm−1
β = 99.643 (1)°	T = 200 K
V = 2342.08 (16) Å3	Platelet, colourless
Z = 4	0.58 × 0.16 × 0.07 mm

Bruker APEXII CCD diffractometer	5775 independent reflections
Radiation source: fine-focus sealed tube	3774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→7
Tmin = 0.417, Tmax = 0.889	k = −32→32
22440 measured reflections	l = −24→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0546P)2 + 2.6613P] where P = (Fo2 + 2Fc2)/3
5775 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.93 e Å−3

	x	y	z	Uiso*/Ueq
Br1	−0.68782 (8)	0.629887 (16)	0.22421 (3)	0.0859 (2)
F1	1.3784 (4)	0.00897 (8)	0.56325 (11)	0.0659 (6)
F2	1.3161 (4)	0.05001 (7)	0.66156 (9)	0.0494 (4)
F3	1.0047 (4)	0.00785 (7)	0.59406 (11)	0.0550 (5)
O1	0.2309 (7)	0.48213 (13)	0.44653 (15)	0.0921 (11)
O2	0.6398 (4)	0.25396 (8)	0.50057 (11)	0.0477 (5)
O3	0.3332 (5)	0.27788 (10)	0.60507 (14)	0.0658 (7)
O4	0.3675 (5)	0.22131 (9)	0.70058 (13)	0.0549 (6)
N1	0.4456 (5)	0.39894 (10)	0.38120 (14)	0.0440 (6)
N2	0.6711 (6)	0.39092 (14)	0.3594 (2)	0.0709 (10)
N3	0.8024 (6)	0.35804 (14)	0.4081 (2)	0.0763 (11)
N4	0.8633 (5)	0.11738 (9)	0.63266 (12)	0.0349 (5)
C1	0.1559 (7)	0.47765 (13)	0.38096 (18)	0.0505 (8)
C2	0.2540 (6)	0.43291 (12)	0.33647 (16)	0.0433 (7)
H2A	0.1080	0.4098	0.3139	0.052*
H2B	0.3301	0.4495	0.2959	0.052*
C3	0.4308 (6)	0.37070 (12)	0.44310 (17)	0.0442 (7)
H3	0.2901	0.3692	0.4692	0.053*
C4	0.6589 (6)	0.34487 (12)	0.46013 (18)	0.0450 (7)
C5	0.7543 (6)	0.30655 (12)	0.52164 (19)	0.0500 (8)
H5A	0.9440	0.3040	0.5290	0.060*
H5B	0.7028	0.3193	0.5682	0.060*
C6	0.7165 (6)	0.21159 (11)	0.54721 (15)	0.0370 (6)
C7	0.6172 (5)	0.20139 (10)	0.61068 (15)	0.0353 (6)
C8	0.7001 (6)	0.15307 (11)	0.65100 (15)	0.0366 (6)
H8	0.6314	0.1462	0.6948	0.044*
C9	0.4265 (6)	0.23796 (12)	0.63684 (17)	0.0417 (7)
C10	0.1823 (7)	0.25434 (14)	0.73111 (19)	0.0539 (8)
H10A	0.0194	0.2565	0.6956	0.065*
H10B	0.2496	0.2918	0.7410	0.065*
C11	0.1379 (11)	0.2287 (2)	0.7998 (2)	0.0903 (16)
H11A	0.0886	0.1905	0.7903	0.135*
H11B	−0.0002	0.2481	0.8186	0.135*
H11C	0.2956	0.2305	0.8365	0.135*
C12	1.2086 (6)	0.03989 (12)	0.59112 (16)	0.0423 (7)
C21	−0.0461 (6)	0.51471 (12)	0.34071 (16)	0.0440 (7)
C22	−0.1286 (6)	0.51169 (13)	0.26558 (16)	0.0451 (7)
H22	−0.0565	0.4853	0.2372	0.054*
C23	−0.3155 (7)	0.54683 (13)	0.23120 (18)	0.0513 (8)
H23	−0.3684	0.5453	0.1791	0.062*
C24	−0.4236 (6)	0.58361 (12)	0.2723 (2)	0.0508 (8)
C25	−0.3501 (10)	0.58660 (17)	0.3464 (2)	0.0862 (15)
H25	−0.4291	0.6121	0.3745	0.103*
C26	−0.1584 (10)	0.55214 (17)	0.3812 (2)	0.0844 (15)
H26	−0.1045	0.5544	0.4332	0.101*
C31	0.8958 (5)	0.17471 (10)	0.52570 (14)	0.0347 (6)
C32	0.9629 (5)	0.12778 (10)	0.56984 (14)	0.0311 (5)
C33	1.1420 (5)	0.09074 (11)	0.54750 (14)	0.0341 (6)
C34	1.2501 (6)	0.10091 (12)	0.48611 (15)	0.0410 (7)
H34	1.3688	0.0756	0.4718	0.049*
C35	1.1872 (7)	0.14842 (13)	0.44408 (16)	0.0470 (7)
H35	1.2669	0.1554	0.4023	0.056*
C36	1.0133 (6)	0.18436 (12)	0.46280 (16)	0.0446 (7)
H36	0.9701	0.2161	0.4337	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.0515 (3)	0.0564 (2)	0.1386 (5)	0.01219 (17)	−0.0170 (2)	0.0347 (2)
F1	0.0879 (16)	0.0592 (12)	0.0565 (12)	0.0408 (11)	0.0290 (11)	0.0074 (9)
F2	0.0566 (12)	0.0539 (10)	0.0370 (9)	0.0161 (9)	0.0060 (8)	0.0067 (8)
F3	0.0720 (13)	0.0296 (8)	0.0640 (12)	−0.0009 (8)	0.0132 (10)	0.0037 (8)
O1	0.128 (3)	0.088 (2)	0.0487 (15)	0.061 (2)	−0.0188 (16)	−0.0027 (14)
O2	0.0599 (14)	0.0324 (10)	0.0452 (11)	0.0068 (9)	−0.0078 (10)	0.0091 (8)
O3	0.0578 (16)	0.0620 (15)	0.0772 (17)	0.0317 (13)	0.0103 (13)	0.0126 (13)
O4	0.0633 (16)	0.0503 (13)	0.0544 (14)	0.0210 (11)	0.0191 (11)	−0.0004 (10)
N1	0.0368 (14)	0.0421 (13)	0.0554 (15)	0.0115 (11)	0.0148 (12)	0.0196 (11)
N2	0.0441 (18)	0.080 (2)	0.097 (2)	0.0258 (15)	0.0346 (17)	0.0470 (19)
N3	0.0405 (18)	0.084 (2)	0.109 (3)	0.0245 (16)	0.0274 (18)	0.054 (2)
N4	0.0402 (14)	0.0305 (11)	0.0347 (12)	0.0042 (10)	0.0082 (10)	0.0039 (9)
C1	0.058 (2)	0.0491 (17)	0.0420 (17)	0.0170 (15)	0.0000 (15)	0.0087 (14)
C2	0.0420 (17)	0.0461 (16)	0.0434 (16)	0.0148 (13)	0.0117 (13)	0.0167 (13)
C3	0.0329 (16)	0.0486 (17)	0.0517 (18)	0.0087 (13)	0.0091 (13)	0.0211 (14)
C4	0.0335 (16)	0.0364 (14)	0.063 (2)	0.0054 (12)	0.0030 (14)	0.0159 (14)
C5	0.0422 (18)	0.0360 (15)	0.066 (2)	0.0021 (13)	−0.0089 (15)	0.0136 (14)
C6	0.0428 (16)	0.0296 (13)	0.0345 (14)	0.0034 (11)	−0.0057 (12)	0.0043 (10)
C7	0.0338 (15)	0.0299 (13)	0.0397 (15)	0.0049 (11)	−0.0016 (12)	−0.0018 (11)
C8	0.0402 (16)	0.0346 (13)	0.0354 (14)	0.0045 (12)	0.0079 (12)	0.0028 (11)
C9	0.0343 (16)	0.0373 (14)	0.0500 (18)	0.0035 (12)	−0.0032 (13)	−0.0038 (12)
C10	0.046 (2)	0.0561 (19)	0.059 (2)	0.0090 (15)	0.0088 (15)	−0.0173 (16)
C11	0.123 (4)	0.093 (3)	0.063 (3)	0.038 (3)	0.041 (3)	−0.002 (2)
C12	0.0488 (19)	0.0375 (15)	0.0416 (16)	0.0141 (13)	0.0103 (13)	0.0011 (12)
C21	0.0514 (19)	0.0389 (15)	0.0404 (16)	0.0131 (13)	0.0038 (13)	0.0070 (12)
C22	0.0502 (19)	0.0439 (16)	0.0394 (16)	0.0094 (14)	0.0028 (13)	0.0052 (12)
C23	0.056 (2)	0.0464 (17)	0.0446 (17)	−0.0030 (15)	−0.0119 (14)	0.0093 (14)
C24	0.0431 (18)	0.0360 (15)	0.070 (2)	0.0113 (13)	−0.0011 (15)	0.0160 (15)
C25	0.116 (4)	0.070 (3)	0.070 (3)	0.061 (3)	0.009 (3)	0.001 (2)
C26	0.132 (4)	0.076 (3)	0.0401 (19)	0.063 (3)	−0.001 (2)	−0.0019 (17)
C31	0.0400 (15)	0.0307 (12)	0.0314 (13)	−0.0003 (11)	0.0002 (11)	0.0019 (10)
C32	0.0324 (14)	0.0285 (12)	0.0311 (13)	−0.0007 (10)	0.0019 (11)	0.0013 (10)
C33	0.0384 (15)	0.0325 (13)	0.0311 (13)	0.0013 (11)	0.0047 (11)	−0.0015 (10)
C34	0.0465 (18)	0.0437 (15)	0.0341 (14)	0.0009 (13)	0.0102 (13)	−0.0050 (12)
C35	0.059 (2)	0.0517 (17)	0.0318 (15)	−0.0047 (15)	0.0123 (14)	0.0011 (13)
C36	0.056 (2)	0.0419 (15)	0.0340 (15)	−0.0027 (14)	0.0031 (13)	0.0090 (12)

Br1—C24	1.897 (3)	C7—C9	1.487 (4)
F1—C12	1.339 (3)	C8—H8	0.9500
F2—C12	1.345 (3)	C10—C11	1.461 (6)
F3—C12	1.341 (4)	C10—H10A	0.9900
O1—C1	1.207 (4)	C10—H10B	0.9900
O2—C6	1.364 (3)	C11—H11A	0.9800
O2—C5	1.448 (4)	C11—H11B	0.9800
O3—C9	1.202 (4)	C11—H11C	0.9800
O4—C9	1.324 (4)	C12—C33	1.491 (4)
O4—C10	1.452 (4)	C21—C26	1.376 (5)
N1—N2	1.333 (4)	C21—C22	1.377 (4)
N1—C3	1.344 (4)	C22—C23	1.380 (4)
N1—C2	1.453 (3)	C22—H22	0.9500
N2—N3	1.311 (4)	C23—C24	1.361 (5)
N3—C4	1.354 (4)	C23—H23	0.9500
N4—C8	1.311 (4)	C24—C25	1.353 (5)
N4—C32	1.369 (4)	C25—C26	1.389 (5)
C1—C21	1.498 (4)	C25—H25	0.9500
C1—C2	1.510 (4)	C26—H26	0.9500
C2—H2A	0.9900	C31—C32	1.417 (3)
C2—H2B	0.9900	C31—C36	1.419 (4)
C3—C4	1.351 (4)	C32—C33	1.420 (4)
C3—H3	0.9500	C33—C34	1.368 (4)
C4—C5	1.490 (4)	C34—C35	1.406 (4)
C5—H5A	0.9900	C34—H34	0.9500
C5—H5B	0.9900	C35—C36	1.358 (5)
C6—C7	1.378 (4)	C35—H35	0.9500
C6—C31	1.413 (4)	C36—H36	0.9500
C7—C8	1.426 (4)
C6—O2—C5	116.3 (2)	C10—C11—H11B	109.5
C9—O4—C10	116.2 (2)	H11A—C11—H11B	109.5
N2—N1—C3	111.0 (2)	C10—C11—H11C	109.5
N2—N1—C2	119.2 (2)	H11A—C11—H11C	109.5
C3—N1—C2	129.7 (3)	H11B—C11—H11C	109.5
N3—N2—N1	106.5 (3)	F1—C12—F3	106.1 (2)
N2—N3—C4	109.4 (3)	F1—C12—F2	105.6 (2)
C8—N4—C32	117.0 (2)	F3—C12—F2	106.4 (2)
O1—C1—C21	121.6 (3)	F1—C12—C33	112.4 (2)
O1—C1—C2	121.3 (3)	F3—C12—C33	113.1 (2)
C21—C1—C2	117.0 (3)	F2—C12—C33	112.7 (2)
N1—C2—C1	112.4 (3)	C26—C21—C22	118.9 (3)
N1—C2—H2A	109.1	C26—C21—C1	118.3 (3)
C1—C2—H2A	109.1	C22—C21—C1	122.8 (3)
N1—C2—H2B	109.1	C21—C22—C23	120.4 (3)
C1—C2—H2B	109.1	C21—C22—H22	119.8
H2A—C2—H2B	107.9	C23—C22—H22	119.8
N1—C3—C4	105.1 (3)	C24—C23—C22	119.6 (3)
N1—C3—H3	127.4	C24—C23—H23	120.2
C4—C3—H3	127.4	C22—C23—H23	120.2
C3—C4—N3	107.9 (3)	C25—C24—C23	121.1 (3)
C3—C4—C5	130.3 (3)	C25—C24—Br1	120.0 (3)
N3—C4—C5	121.8 (3)	C23—C24—Br1	118.8 (3)
O2—C5—C4	106.6 (2)	C24—C25—C26	119.6 (3)
O2—C5—H5A	110.4	C24—C25—H25	120.2
C4—C5—H5A	110.4	C26—C25—H25	120.2
O2—C5—H5B	110.4	C21—C26—C25	120.3 (3)
C4—C5—H5B	110.4	C21—C26—H26	119.9
H5A—C5—H5B	108.6	C25—C26—H26	119.9
O2—C6—C7	123.6 (3)	C6—C31—C32	118.3 (2)
O2—C6—C31	117.0 (3)	C6—C31—C36	121.7 (2)
C7—C6—C31	119.2 (2)	C32—C31—C36	119.9 (3)
C6—C7—C8	117.5 (2)	N4—C32—C31	122.6 (2)
C6—C7—C9	122.5 (2)	N4—C32—C33	119.5 (2)
C8—C7—C9	119.9 (3)	C31—C32—C33	117.9 (2)
N4—C8—C7	125.4 (3)	C34—C33—C32	120.7 (2)
N4—C8—H8	117.3	C34—C33—C12	120.1 (3)
C7—C8—H8	117.3	C32—C33—C12	119.2 (2)
O3—C9—O4	122.8 (3)	C33—C34—C35	120.7 (3)
O3—C9—C7	125.4 (3)	C33—C34—H34	119.7
O4—C9—C7	111.8 (2)	C35—C34—H34	119.7
O4—C10—C11	108.0 (3)	C36—C35—C34	120.4 (3)
O4—C10—H10A	110.1	C36—C35—H35	119.8
C11—C10—H10A	110.1	C34—C35—H35	119.8
O4—C10—H10B	110.1	C35—C36—C31	120.3 (3)
C11—C10—H10B	110.1	C35—C36—H36	119.9
H10A—C10—H10B	108.4	C31—C36—H36	119.9
C10—C11—H11A	109.5
C3—N1—N2—N3	−0.8 (5)	C26—C21—C22—C23	2.0 (6)
C2—N1—N2—N3	−178.3 (3)	C1—C21—C22—C23	180.0 (3)
N1—N2—N3—C4	0.6 (5)	C21—C22—C23—C24	−1.9 (5)
N2—N1—C2—C1	−127.2 (3)	C22—C23—C24—C25	0.4 (6)
C3—N1—C2—C1	55.8 (5)	C22—C23—C24—Br1	−178.0 (3)
O1—C1—C2—N1	−1.4 (5)	C23—C24—C25—C26	1.0 (7)
C21—C1—C2—N1	−179.0 (3)	Br1—C24—C25—C26	179.3 (4)
N2—N1—C3—C4	0.7 (4)	C22—C21—C26—C25	−0.6 (7)
C2—N1—C3—C4	177.9 (3)	C1—C21—C26—C25	−178.7 (4)
N1—C3—C4—N3	−0.3 (4)	C24—C25—C26—C21	−0.8 (8)
N1—C3—C4—C5	−178.3 (3)	O2—C6—C31—C32	−174.8 (2)
N2—N3—C4—C3	−0.2 (5)	C7—C6—C31—C32	1.3 (4)
N2—N3—C4—C5	178.1 (3)	O2—C6—C31—C36	6.8 (4)
C6—O2—C5—C4	175.5 (3)	C7—C6—C31—C36	−177.1 (3)
C3—C4—C5—O2	78.5 (5)	C8—N4—C32—C31	0.0 (4)
N3—C4—C5—O2	−99.2 (4)	C8—N4—C32—C33	179.6 (3)
C5—O2—C6—C7	81.6 (4)	C6—C31—C32—N4	−0.9 (4)
C5—O2—C6—C31	−102.5 (3)	C36—C31—C32—N4	177.5 (3)
O2—C6—C7—C8	175.0 (3)	C6—C31—C32—C33	179.6 (2)
C31—C6—C7—C8	−0.9 (4)	C36—C31—C32—C33	−2.1 (4)
O2—C6—C7—C9	−3.8 (4)	N4—C32—C33—C34	−178.1 (3)
C31—C6—C7—C9	−179.6 (3)	C31—C32—C33—C34	1.4 (4)
C32—N4—C8—C7	0.5 (4)	N4—C32—C33—C12	2.8 (4)
C6—C7—C8—N4	0.0 (4)	C31—C32—C33—C12	−177.6 (3)
C9—C7—C8—N4	178.7 (3)	F1—C12—C33—C34	0.6 (4)
C10—O4—C9—O3	−0.3 (5)	F3—C12—C33—C34	−119.5 (3)
C10—O4—C9—C7	179.9 (3)	F2—C12—C33—C34	119.8 (3)
C6—C7—C9—O3	3.1 (5)	F1—C12—C33—C32	179.7 (3)
C8—C7—C9—O3	−175.6 (3)	F3—C12—C33—C32	59.6 (3)
C6—C7—C9—O4	−177.2 (3)	F2—C12—C33—C32	−61.1 (4)
C8—C7—C9—O4	4.1 (4)	C32—C33—C34—C35	0.4 (4)
C9—O4—C10—C11	178.5 (3)	C12—C33—C34—C35	179.4 (3)
O1—C1—C21—C26	−4.3 (6)	C33—C34—C35—C36	−1.6 (5)
C2—C1—C21—C26	173.3 (4)	C34—C35—C36—C31	0.9 (5)
O1—C1—C21—C22	177.7 (4)	C6—C31—C36—C35	179.3 (3)
C2—C1—C21—C22	−4.7 (5)	C32—C31—C36—C35	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N2i	0.99	2.62	3.339 (4)	129
C3—H3···N3i	0.95	2.65	3.288 (4)	125
C2—H2B···F2ii	0.99	2.45	3.308 (3)	144
C5—H5A···O3iii	0.99	2.37	3.258 (4)	149
C26—H26···O1iv	0.95	2.57	3.354 (5)	140
C34—H34···F1	0.95	2.34	2.687 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N2i	0.99	2.62	3.339 (4)	129
C3—H3⋯N3i	0.95	2.65	3.288 (4)	125
C2—H2B⋯F2ii	0.99	2.45	3.308 (3)	144
C5—H5A⋯O3iii	0.99	2.37	3.258 (4)	149
C26—H26⋯O1iv	0.95	2.57	3.354 (5)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .