Literature DB >> 21754442

8-(2,2,2-Trifluoro-ethoxy)quinolinium perchlorate-8-(2,2,2-trifluoro-ethoxy)quinoline (1/1).

Jun Wu¹, Lu-Sheng Chen, Qi-Kui Liu, Dian-Shun Guo.

Abstract

The title compound, C(11)H(9)F(3)NO(+)·ClO(4) (-)·C(11)H(8)F(3)NO or [(C(11)H(8)F(3)NO)H(C(11)H(8)F(3)NO)]ClO(4), contains two 8-(2,2,2-trifluoro-eth--oxy)quinoline molecules, one of which combines a proton from perchloric acid to form the corresponding quinolinium cation. The quinolinium and quinoline rings form a cationic unit via an inter-molecular N-H⋯N hydrogen bond. The heterocyclic units are almost perpendicular to each other [inter-planar angle 86.97 (6)°]. In the crystal, each perchlorate anion bridges two adjacent cationic units and creates a chain by a combination of C-H⋯O hydrogen bonds. Two inversion-related chains associate into a mol-ecular column by π-π stacking inter-actions between the quinolinium rings. The perpendicular and centroid-centroid distances between adjacent quinolinium rings are 3.501 (3) and 3.634 (9) Å, respectively. The molecular column is linked to its neighbors, creating a two-dimensional network via the weak π-π stacking between the quinoline rings [perpendicular and centroid-centroid separations 3.340 (4) and 4.408 (4) Å, respectively]. Finally, a three-dimensional framework is formed by a combination of intermolecular C-F⋯π contacts. One -CF(3) group is disordered over two positions of equal occupancy.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21754442 PMCID： PMC3089229 DOI： 10.1107/S1600536811013250

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to quinoline derivatives, see: Moret et al. (2006 ▶); Kalita et al. (2009 ▶). For related structures, see: Ouyang & Khoo et al. (1998 ▶); Karmakar et al. (2009 ▶); Al-Mandhary & Steel (2003 ▶); Zhang et al. (2006 ▶); Zheng et al. (2006 ▶). For π–π stacking, see: Kalita & Baruah (2010 ▶); Chen et al. (2005 ▶); Liang et al. (2002 ▶). For C—F⋯π contacts, see: Prasanna & Row (2000 ▶); Saraogi et al. (2003 ▶); Choudhury & Row (2004 ▶).

Experimental

Crystal data

C11H9F3NO+·ClO4 −·C11H8F3NO M = 554.83 Triclinic, a = 9.462 (2) Å b = 11.229 (3) Å c = 11.832 (3) Å α = 82.910 (3)° β = 77.048 (3)° γ = 74.536 (3)° V = 1178.0 (5) Å3 Z = 2 Mo Kα radiation μ = 0.25 mm−1 T = 293 K 0.50 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.884, T max = 0.940 6301 measured reflections 4364 independent reflections 3400 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.137 S = 1.02 4364 reflections 361 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013250/im2278sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013250/im2278Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₉F₃NO⁺·ClO₄⁻·C₁₁H₈F₃NO	Z = 2
M_r = 554.83	F(000) = 564
Triclinic, P1	D_x = 1.564 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.462 (2) Å	Cell parameters from 2404 reflections
b = 11.229 (3) Å	θ = 2.5–25.1°
c = 11.832 (3) Å	µ = 0.25 mm⁻¹
α = 82.910 (3)°	T = 293 K
β = 77.048 (3)°	Block, colourless
γ = 74.536 (3)°	0.50 × 0.32 × 0.25 mm
V = 1178.0 (5) Å³

Bruker SMART CCD area-detector diffractometer	4364 independent reflections
Radiation source: fine-focus sealed tube	3400 reflections with I > 2σ(I)
graphite	R_int = 0.021
phi and ω scans	θ_max = 25.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→8
T_min = 0.884, T_max = 0.940	k = −13→9
6301 measured reflections	l = −14→14

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.068P)² + 0.293P] where P = (F_o² + 2F_c²)/3
4364 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Experimental. ^1Ĥ NMR (300 MHz, CDCl~3~):δ 8.97 (dd, 1H, J = 4.04 Hz, 1.52 Hz), 8.17 (d, 1H, J = 7.52 Hz), 7.54–7.44 (m, 3H), 7.25 (d, H, J = 7.65 Hz), 4.78 (q, 2H, J = 8.33 Hz).

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.1468 (3)	0.6885 (3)	0.6473 (2)	0.0583 (6)
H1	1.1569	0.6034	0.6558	0.070*
C2	1.2727 (3)	0.7332 (3)	0.6049 (2)	0.0694 (8)
H2	1.3662	0.6791	0.5845	0.083*
C3	1.2575 (3)	0.8571 (3)	0.5937 (2)	0.0682 (8)
H3	1.3416	0.8880	0.5653	0.082*
C4	1.1164 (3)	0.9399 (2)	0.6243 (2)	0.0548 (6)
C5	0.9930 (3)	0.8878 (2)	0.66440 (18)	0.0448 (5)
C6	1.0927 (4)	1.0696 (3)	0.6165 (2)	0.0677 (8)
H6	1.1731	1.1056	0.5909	0.081*
C7	0.9530 (4)	1.1412 (3)	0.6463 (2)	0.0738 (8)
H7	0.9385	1.2268	0.6415	0.089*
C8	0.8288 (3)	1.0905 (2)	0.6843 (2)	0.0643 (7)
H8	0.7334	1.1424	0.7027	0.077*
C9	0.8474 (3)	0.9661 (2)	0.6943 (2)	0.0505 (6)
C10	0.5911 (3)	0.9754 (3)	0.7691 (3)	0.0844 (10)
H10A	0.5518	1.0228	0.7037	0.101*
H10B	0.5902	1.0325	0.8245	0.101*
C12	0.7912 (3)	0.5853 (2)	0.6481 (2)	0.0637 (7)
H12	0.8219	0.6259	0.5770	0.076*
C13	0.7078 (4)	0.4983 (3)	0.6515 (3)	0.0731 (8)
H13	0.6806	0.4839	0.5845	0.088*
C14	0.6678 (3)	0.4362 (2)	0.7528 (3)	0.0687 (8)
H14	0.6140	0.3772	0.7557	0.082*
C15	0.7062 (3)	0.4590 (2)	0.8546 (2)	0.0533 (6)
C16	0.7845 (2)	0.55191 (19)	0.8454 (2)	0.0449 (5)
C17	0.6663 (3)	0.3978 (2)	0.9643 (3)	0.0664 (7)
H17	0.6164	0.3355	0.9710	0.080*
C18	0.7003 (3)	0.4296 (2)	1.0592 (3)	0.0670 (7)
H18	0.6739	0.3884	1.1308	0.080*
C19	0.7750 (3)	0.5238 (2)	1.0520 (2)	0.0574 (6)
H19	0.7962	0.5450	1.1188	0.069*
C20	0.8163 (2)	0.5841 (2)	0.9478 (2)	0.0465 (5)
C21	0.9028 (3)	0.7245 (2)	1.0323 (2)	0.0550 (6)
H21A	0.9774	0.6653	1.0687	0.066*
H21B	0.8083	0.7397	1.0876	0.066*
C22	0.9496 (3)	0.8415 (3)	0.9960 (2)	0.0621 (7)
Cl1	0.35067 (7)	0.30823 (6)	0.64594 (5)	0.0564 (2)
F4	0.9743 (3)	0.88475 (17)	1.08657 (15)	0.0965 (6)
F5	1.07304 (19)	0.82890 (16)	0.91311 (15)	0.0783 (5)
F6	0.8460 (2)	0.92888 (15)	0.95375 (16)	0.0850 (5)
N1	1.0134 (2)	0.76298 (17)	0.67574 (16)	0.0463 (4)
H1A	0.9374	0.7321	0.7021	0.056*
N2	0.8280 (2)	0.61195 (17)	0.74111 (17)	0.0482 (5)
O1	0.73864 (18)	0.90405 (15)	0.73088 (16)	0.0613 (5)
O2	0.88758 (18)	0.67771 (15)	0.93048 (13)	0.0526 (4)
O3	0.4147 (3)	0.4098 (2)	0.6013 (2)	0.0932 (7)
O4	0.4074 (2)	0.25456 (19)	0.74758 (18)	0.0835 (6)
O5	0.3897 (3)	0.2197 (2)	0.5613 (2)	0.0979 (8)
O6	0.1932 (2)	0.3522 (2)	0.6752 (2)	0.0888 (7)
C11	0.4994 (4)	0.8884 (4)	0.8241 (4)	0.0902 (10)	0.50
F1	0.5026 (16)	0.8110 (15)	0.7456 (17)	0.177 (7)	0.50
F2	0.3618 (17)	0.9521 (18)	0.8772 (11)	0.131 (4)	0.50
F3	0.5473 (15)	0.8205 (11)	0.9134 (14)	0.118 (5)	0.50
C11W	0.4994 (4)	0.8884 (4)	0.8241 (4)	0.0902 (10)	0.50
F1W	0.5117 (10)	0.7933 (8)	0.7704 (12)	0.105 (4)	0.50
F2W	0.3555 (16)	0.9444 (18)	0.8260 (11)	0.109 (3)	0.50
F3W	0.5318 (19)	0.8454 (16)	0.9246 (13)	0.142 (6)	0.50

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0535 (15)	0.0587 (15)	0.0562 (15)	−0.0040 (12)	−0.0086 (12)	−0.0055 (12)
C2	0.0472 (15)	0.085 (2)	0.0672 (18)	−0.0088 (14)	−0.0025 (13)	−0.0029 (15)
C3	0.0540 (16)	0.094 (2)	0.0623 (17)	−0.0336 (15)	−0.0074 (13)	−0.0012 (15)
C4	0.0612 (16)	0.0688 (16)	0.0412 (13)	−0.0279 (13)	−0.0108 (11)	−0.0022 (11)
C5	0.0539 (13)	0.0484 (13)	0.0347 (11)	−0.0179 (11)	−0.0090 (10)	−0.0007 (9)
C6	0.087 (2)	0.0718 (18)	0.0563 (16)	−0.0452 (17)	−0.0110 (15)	0.0005 (13)
C7	0.116 (3)	0.0494 (15)	0.0600 (17)	−0.0323 (17)	−0.0124 (17)	−0.0016 (13)
C8	0.0779 (18)	0.0474 (14)	0.0599 (16)	−0.0087 (13)	−0.0078 (14)	−0.0004 (12)
C9	0.0564 (14)	0.0476 (13)	0.0445 (13)	−0.0114 (11)	−0.0081 (11)	0.0008 (10)
C10	0.0535 (17)	0.0661 (18)	0.111 (3)	0.0037 (14)	0.0015 (16)	0.0071 (17)
C12	0.0788 (19)	0.0615 (16)	0.0556 (16)	−0.0193 (14)	−0.0209 (14)	−0.0046 (12)
C13	0.085 (2)	0.0695 (18)	0.080 (2)	−0.0252 (16)	−0.0348 (17)	−0.0145 (16)
C14	0.0658 (18)	0.0522 (15)	0.099 (2)	−0.0214 (13)	−0.0283 (16)	−0.0109 (15)
C15	0.0451 (13)	0.0400 (12)	0.0764 (17)	−0.0112 (10)	−0.0144 (12)	−0.0041 (11)
C16	0.0404 (12)	0.0361 (11)	0.0566 (14)	−0.0069 (9)	−0.0101 (10)	−0.0027 (10)
C17	0.0574 (16)	0.0501 (15)	0.093 (2)	−0.0240 (12)	−0.0120 (15)	0.0066 (14)
C18	0.0654 (17)	0.0598 (16)	0.0700 (18)	−0.0220 (14)	−0.0037 (14)	0.0135 (13)
C19	0.0573 (15)	0.0566 (15)	0.0567 (15)	−0.0169 (12)	−0.0069 (12)	0.0003 (12)
C20	0.0437 (12)	0.0412 (12)	0.0534 (14)	−0.0109 (10)	−0.0062 (10)	−0.0035 (10)
C21	0.0618 (15)	0.0595 (15)	0.0467 (13)	−0.0199 (12)	−0.0097 (11)	−0.0066 (11)
C22	0.0790 (19)	0.0619 (16)	0.0541 (15)	−0.0259 (15)	−0.0184 (14)	−0.0094 (12)
Cl1	0.0547 (4)	0.0556 (4)	0.0571 (4)	−0.0178 (3)	−0.0036 (3)	−0.0017 (3)
F4	0.1570 (19)	0.0919 (12)	0.0696 (11)	−0.0634 (13)	−0.0396 (12)	−0.0119 (9)
F5	0.0817 (11)	0.0814 (11)	0.0788 (11)	−0.0408 (9)	−0.0069 (9)	−0.0032 (9)
F6	0.1038 (13)	0.0591 (10)	0.0926 (13)	−0.0115 (9)	−0.0315 (11)	−0.0039 (9)
N1	0.0444 (11)	0.0473 (11)	0.0459 (11)	−0.0131 (9)	−0.0054 (8)	−0.0011 (8)
N2	0.0519 (11)	0.0442 (10)	0.0500 (11)	−0.0117 (9)	−0.0124 (9)	−0.0051 (8)
O1	0.0449 (9)	0.0506 (10)	0.0792 (12)	−0.0075 (8)	−0.0004 (8)	−0.0011 (9)
O2	0.0648 (10)	0.0551 (9)	0.0453 (9)	−0.0284 (8)	−0.0091 (8)	−0.0050 (7)
O3	0.1065 (17)	0.0857 (15)	0.1007 (17)	−0.0546 (14)	−0.0250 (13)	0.0195 (12)
O4	0.0875 (15)	0.0769 (13)	0.0738 (13)	−0.0045 (11)	−0.0184 (11)	0.0110 (11)
O5	0.0924 (16)	0.1109 (18)	0.0948 (16)	−0.0381 (14)	0.0101 (13)	−0.0478 (14)
O6	0.0554 (12)	0.0968 (16)	0.1055 (17)	−0.0104 (11)	−0.0081 (11)	−0.0077 (13)
C11	0.0475 (18)	0.089 (3)	0.120 (4)	−0.0082 (17)	0.0047 (19)	−0.010 (3)
F1	0.109 (7)	0.217 (14)	0.235 (12)	−0.025 (7)	−0.069 (7)	−0.097 (10)
F2	0.054 (5)	0.124 (6)	0.179 (12)	0.000 (4)	0.034 (7)	−0.030 (9)
F3	0.084 (5)	0.082 (3)	0.155 (12)	−0.026 (3)	0.021 (5)	0.038 (5)
C11W	0.0475 (18)	0.089 (3)	0.120 (4)	−0.0082 (17)	0.0047 (19)	−0.010 (3)
F1W	0.056 (4)	0.077 (4)	0.181 (9)	−0.031 (3)	0.001 (4)	−0.023 (5)
F2W	0.045 (3)	0.128 (5)	0.143 (8)	−0.010 (3)	0.007 (5)	−0.041 (7)
F3W	0.142 (11)	0.194 (13)	0.093 (7)	−0.070 (9)	−0.007 (6)	0.002 (7)

C1—N1	1.312 (3)	C14—H14	0.9300
C1—C2	1.383 (4)	C15—C16	1.413 (3)
C1—H1	0.9300	C15—C17	1.414 (4)
C2—C3	1.352 (4)	C16—N2	1.364 (3)
C2—H2	0.9300	C16—C20	1.421 (3)
C3—C4	1.408 (4)	C17—C18	1.346 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.406 (3)	C18—C19	1.404 (4)
C4—C6	1.408 (4)	C18—H18	0.9300
C5—N1	1.357 (3)	C19—C20	1.361 (3)
C5—C9	1.418 (3)	C19—H19	0.9300
C6—C7	1.346 (4)	C20—O2	1.365 (3)
C6—H6	0.9300	C21—O2	1.422 (3)
C7—C8	1.401 (4)	C21—C22	1.480 (4)
C7—H7	0.9300	C21—H21A	0.9700
C8—C9	1.354 (3)	C21—H21B	0.9700
C8—H8	0.9300	C22—F4	1.319 (3)
C9—O1	1.357 (3)	C22—F6	1.326 (3)
C10—O1	1.416 (3)	C22—F5	1.334 (3)
C10—C11	1.474 (5)	Cl1—O6	1.415 (2)
C10—H10A	0.9700	Cl1—O5	1.418 (2)
C10—H10B	0.9700	Cl1—O3	1.423 (2)
C12—N2	1.316 (3)	Cl1—O4	1.427 (2)
C12—C13	1.402 (4)	N1—H1A	0.8600
C12—H12	0.9300	C11—F3	1.317 (15)
C13—C14	1.341 (4)	C11—F1	1.338 (17)
C13—H13	0.9300	C11—F2	1.359 (15)
C14—C15	1.403 (4)

N1—C1—C2	121.7 (3)	N2—C16—C15	121.5 (2)
N1—C1—H1	119.1	N2—C16—C20	119.7 (2)
C2—C1—H1	119.1	C15—C16—C20	118.8 (2)
C3—C2—C1	118.9 (3)	C18—C17—C15	120.2 (2)
C3—C2—H2	120.6	C18—C17—H17	119.9
C1—C2—H2	120.6	C15—C17—H17	119.9
C2—C3—C4	121.0 (3)	C17—C18—C19	121.3 (3)
C2—C3—H3	119.5	C17—C18—H18	119.4
C4—C3—H3	119.5	C19—C18—H18	119.4
C5—C4—C6	119.0 (3)	C20—C19—C18	120.3 (3)
C5—C4—C3	116.9 (2)	C20—C19—H19	119.8
C6—C4—C3	124.1 (3)	C18—C19—H19	119.8
N1—C5—C4	120.2 (2)	C19—C20—O2	125.5 (2)
N1—C5—C9	120.1 (2)	C19—C20—C16	120.1 (2)
C4—C5—C9	119.8 (2)	O2—C20—C16	114.40 (19)
C7—C6—C4	119.7 (3)	O2—C21—C22	107.24 (19)
C7—C6—H6	120.2	O2—C21—H21A	110.3
C4—C6—H6	120.2	C22—C21—H21A	110.3
C6—C7—C8	121.9 (3)	O2—C21—H21B	110.3
C6—C7—H7	119.0	C22—C21—H21B	110.3
C8—C7—H7	119.0	H21A—C21—H21B	108.5
C9—C8—C7	120.1 (3)	F4—C22—F6	107.2 (2)
C9—C8—H8	119.9	F4—C22—F5	108.3 (2)
C7—C8—H8	119.9	F6—C22—F5	105.6 (2)
C8—C9—O1	126.7 (2)	F4—C22—C21	109.5 (2)
C8—C9—C5	119.5 (2)	F6—C22—C21	112.6 (2)
O1—C9—C5	113.7 (2)	F5—C22—C21	113.3 (2)
O1—C10—C11	107.3 (2)	O6—Cl1—O5	109.93 (14)
O1—C10—H10A	110.3	O6—Cl1—O3	109.00 (14)
C11—C10—H10A	110.3	O5—Cl1—O3	109.86 (15)
O1—C10—H10B	110.3	O6—Cl1—O4	109.81 (14)
C11—C10—H10B	110.3	O5—Cl1—O4	110.33 (15)
H10A—C10—H10B	108.5	O3—Cl1—O4	107.87 (14)
N2—C12—C13	122.8 (3)	C1—N1—C5	121.2 (2)
N2—C12—H12	118.6	C1—N1—H1A	119.4
C13—C12—H12	118.6	C5—N1—H1A	119.4
C14—C13—C12	118.9 (3)	C12—N2—C16	118.9 (2)
C14—C13—H13	120.5	C9—O1—C10	117.2 (2)
C12—C13—H13	120.5	C20—O2—C21	116.17 (18)
C13—C14—C15	120.8 (3)	F3—C11—F1	107.5 (10)
C13—C14—H14	119.6	F3—C11—F2	100.6 (10)
C15—C14—H14	119.6	F1—C11—F2	116.5 (9)
C14—C15—C16	117.0 (2)	F3—C11—C10	113.4 (7)
C14—C15—C17	123.7 (2)	F1—C11—C10	108.9 (8)
C16—C15—C17	119.3 (2)	F2—C11—C10	109.9 (9)

N1—C1—C2—C3	0.6 (4)	C16—C15—C17—C18	1.2 (4)
C1—C2—C3—C4	0.0 (4)	C15—C17—C18—C19	0.3 (4)
C2—C3—C4—C5	−1.3 (4)	C17—C18—C19—C20	−0.8 (4)
C2—C3—C4—C6	179.0 (3)	C18—C19—C20—O2	179.2 (2)
C6—C4—C5—N1	−178.2 (2)	C18—C19—C20—C16	−0.2 (4)
C3—C4—C5—N1	2.1 (3)	N2—C16—C20—C19	−179.2 (2)
C6—C4—C5—C9	1.1 (3)	C15—C16—C20—C19	1.7 (3)
C3—C4—C5—C9	−178.7 (2)	N2—C16—C20—O2	1.3 (3)
C5—C4—C6—C7	−0.7 (4)	C15—C16—C20—O2	−177.81 (19)
C3—C4—C6—C7	179.0 (3)	O2—C21—C22—F4	−176.1 (2)
C4—C6—C7—C8	−0.6 (4)	O2—C21—C22—F6	64.7 (3)
C6—C7—C8—C9	1.4 (4)	O2—C21—C22—F5	−55.0 (3)
C7—C8—C9—O1	179.3 (2)	C2—C1—N1—C5	0.2 (4)
C7—C8—C9—C5	−0.9 (4)	C4—C5—N1—C1	−1.6 (3)
N1—C5—C9—C8	179.0 (2)	C9—C5—N1—C1	179.1 (2)
C4—C5—C9—C8	−0.3 (3)	C13—C12—N2—C16	0.6 (4)
N1—C5—C9—O1	−1.2 (3)	C15—C16—N2—C12	2.4 (3)
C4—C5—C9—O1	179.6 (2)	C20—C16—N2—C12	−176.7 (2)
N2—C12—C13—C14	−2.4 (4)	C8—C9—O1—C10	−3.9 (4)
C12—C13—C14—C15	1.1 (4)	C5—C9—O1—C10	176.3 (2)
C13—C14—C15—C16	1.6 (4)	C11—C10—O1—C9	−169.7 (3)
C13—C14—C15—C17	179.3 (3)	C19—C20—O2—C21	−7.9 (3)
C14—C15—C16—N2	−3.5 (3)	C16—C20—O2—C21	171.53 (19)
C17—C15—C16—N2	178.8 (2)	C22—C21—O2—C20	−167.1 (2)
C14—C15—C16—C20	175.6 (2)	O1—C10—C11—F3	59.6 (8)
C17—C15—C16—C20	−2.2 (3)	O1—C10—C11—F1	−60.0 (9)
C14—C15—C17—C18	−176.4 (3)	O1—C10—C11—F2	171.3 (6)

Cg1, Cg2 and Cg3 are the midpoints of the N1–C5, C5–C9 and C17–C18 bonds, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.86	1.87	2.684 (3)	158
C22—F5···Cg1	1.33	3.10	3.796 (3)	111
C22—F6···Cg2	1.33	3.17	3.804 (4)	109
C13—H13···O3ⁱ	0.93	2.60	3.393 (6)	144.
C21—H21B···O4ⁱⁱ	0.97	2.48	3.437 (7)	169
C22—F5···Cg3ⁱⁱⁱ	1.33	3.24	3.860 (8)	108

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the midpoints of the N1–C5, C5–C9 and C17–C18 bonds, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2	0.86	1.87	2.684 (3)	158
C22—F5⋯Cg1	1.33	3.10	3.796 (3)	111
C22—F6⋯Cg2	1.33	3.17	3.804 (4)	109
C13—H13⋯O3ⁱ	0.93	2.60	3.393 (6)	144
C21—H21B⋯O4ⁱⁱ	0.97	2.48	3.437 (7)	169
C22—F5⋯Cg3ⁱⁱⁱ	1.33	3.24	3.860 (8)	108

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and anti-HIV properties of new hydroxyquinoline-polyamine conjugates on cells infected by HIV-1 LAV and HIV-1 BaL viral strains.

Authors: Vincent Moret; Nathalie Dereudre-Bosquet; Pascal Clayette; Younes Laras; Nicolas Pietrancosta; Amandine Rolland; Clement Weck; Sylvain Marc; Jean-Louis Kraus
Journal: Bioorg Med Chem Lett Date: 2006-09-26 Impact factor: 2.823

2 in total