1-(3,5-Dimeth­oxy­phen­yl)-2-(4-fluoro­phen­yl)-4,5-dimethyl-1H-imidazole

Rosepriya, S.; Thiruvalluvar, A.; Saravanan, K.; Jayabharathi, J.; Butcher, R.J.

doi:10.1107/S1600536811055012

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o256

doi:10.1107/S1600536811055012

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1-(3,5-Dimethoxyphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole

S. Rosepriya,^a A. Thiruvalluvar,^a ^* K. Saravanan,^b J. Jayabharathi ^b and Ray J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 20 December 2011; accepted 21 December 2011; online 7 January 2012)

In the title compound, C₁₉H₁₉FN₂O₂, the imidazole ring is essentially planar [maximum deviation = 0.0030 (8) Å] and makes dihedral angles of 66.45 (7) and 29.98 (7)° with the benzene rings attached to the ring N and C atoms, respectively. The dihedral angle between the two benzene rings is 64.79 (7)°. A C—H⋯π interaction is found in the crystal structure. The two methoxy groups were found to be disordered over two sets of sites with occupancy factors of 0.803 (4) and 0.197 (4). The F atom is disordered over two sites with occupancy factors of 0.929 (4) and 0.071 (4).

Related literature

For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992 ); Jackson et al. (2000 ); Banfi et al. (2006 ). For a related structure and applications of imidazole derivatives, see: Rosepriya et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₉FN₂O₂
M_r = 326.36
Monoclinic, P 2₁ /n
a = 6.9654 (1) Å
b = 17.8520 (3) Å
c = 13.7121 (3) Å
β = 97.833 (2)°
V = 1689.14 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 295 K
0.47 × 0.38 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.558, T_max = 1.000
7744 measured reflections
3533 independent reflections
2723 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.138
S = 1.06
3533 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2/N3/C4/C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯Cg1ⁱ	0.93	2.99	3.8714 (16)	159
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055012/hg5156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055012/hg5156Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055012/hg5156Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811055012/hg5156Isup4.cml

checkCIF report

Comment top

For multidrug-resistant Tuberculosis (Dooley et al.,(1992)), antifungal and antimycobacterial activity (Banfi et al. 2006), and bactericidal effects (Jackson et al. 2000), the use of imidazole based compounds were reported. Rosepriya et al. 2011 have reported the crystal structure of 1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole. As part of our research (Rosepriya et al. 2011), we have synthesized the title compound (I) and report its crystal structure here.

In the title compound, Fig. 1, C₁₉H₁₉FN₂O₂, the imidazole ring is essentially planar [maximum deviation of 0.0030 (8) Å for C4]. The imidazole ring makes dihedral angles of 66.45 (7) and 29.98 (7)° with the benzene rings attached to nitrogen and carbon, respectively. The dihedral angle between the two benzene rings is 64.79 (7)°. A C23—H23···π interaction involving the imidazole (N1,C2,N3,C4,C5) ring is found in the crystal structure (Table 1). The two methoxy groups at C13 and C15 were found to be disordered over two positions with occupancy factors of 0.803 (4) and 0.197 (4). The F atom at C24 is disordered over two positions with occupancy factors of 0.929 (4) and 0.071 (4).

Related literature top

For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992); Jackson et al. (2000); Banfi et al. (2006). For a related structure and applications of imidazole derivatives, see: Rosepriya et al. (2011).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), 3,5-dimethoxyaniline (2.29 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-fluorobenzaldehyde (1.8 g, 15 mmol) was added over 1 hr with the temperature maintained at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using Hexane: Ethyl acetate as the eluent. Yield: 2.20 g (45%). Crystals suitable for X-ray diffraction studies were grown by slow solvent evaporation of a solution of the compound in dichloromethane.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. The minor component of methoxy and F atoms are omitted for clarity.

1-(3,5-Dimethoxyphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole top

Crystal data top

C₁₉H₁₉FN₂O₂	F(000) = 688
M_r = 326.36	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 420 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 6.9654 (1) Å	Cell parameters from 3957 reflections
b = 17.8520 (3) Å	θ = 5.0–77.4°
c = 13.7121 (3) Å	µ = 0.75 mm⁻¹
β = 97.833 (2)°	T = 295 K
V = 1689.14 (5) Å³	Plate, colourless
Z = 4	0.47 × 0.38 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3533 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2723 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.6°, θ_min = 5.0°
ω scans	h = −4→8
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010)	k = −22→21
T_min = 0.558, T_max = 1.000	l = −17→17
7744 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0917P)² + 0.0185P] where P = (F_o² + 2F_c²)/3
3533 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₉FN₂O₂	V = 1689.14 (5) Å³
M_r = 326.36	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.9654 (1) Å	µ = 0.75 mm⁻¹
b = 17.8520 (3) Å	T = 295 K
c = 13.7121 (3) Å	0.47 × 0.38 × 0.16 mm
β = 97.833 (2)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3533 independent reflections
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010)	2723 reflections with I > 2σ(I)
T_min = 0.558, T_max = 1.000	R_int = 0.024
7744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
3533 reflections	Δρ_min = −0.18 e Å⁻³
240 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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.

A damping factor (DAMP 200 15 in the final refinement cycles) was applied to avoid large displacements of the less occupied methoxy and fluorine atoms with EADP F4A F4B, EADP O13A O13B, EADP O15A O15B, EADP C17A C17B, EADP C18A C18B.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
F4A	−0.29421 (17)	0.18280 (10)	0.14002 (10)	0.0827 (4)	0.929 (4)
O13A	0.7091 (3)	0.45839 (10)	0.22912 (15)	0.0748 (6)	0.803 (4)
O15A	0.2065 (3)	0.45966 (11)	0.43181 (19)	0.0728 (6)	0.803 (4)
N1	0.55071 (14)	0.23172 (5)	0.40039 (8)	0.0452 (3)
N3	0.48548 (15)	0.11225 (6)	0.42587 (9)	0.0513 (3)
C2	0.42077 (16)	0.17418 (6)	0.38065 (9)	0.0446 (3)
C4	0.66338 (17)	0.12988 (7)	0.47766 (10)	0.0513 (3)
C5	0.70736 (16)	0.20299 (7)	0.46281 (10)	0.0493 (3)
C11	0.52171 (16)	0.30968 (6)	0.37642 (9)	0.0459 (3)
C12	0.64059 (19)	0.34342 (7)	0.31551 (11)	0.0533 (4)
C13	0.6101 (2)	0.41860 (8)	0.29299 (12)	0.0600 (4)
C14	0.4653 (2)	0.45903 (7)	0.33020 (13)	0.0643 (5)
C15	0.3491 (2)	0.42387 (7)	0.38983 (11)	0.0564 (4)
C16	0.37798 (17)	0.34825 (7)	0.41430 (10)	0.0502 (4)
C17A	0.8558 (4)	0.4227 (2)	0.1871 (3)	0.0874 (9)	0.803 (4)
C18A	0.1764 (5)	0.53712 (15)	0.4144 (3)	0.0865 (12)	0.803 (4)
C21	0.23453 (16)	0.17930 (6)	0.31576 (9)	0.0446 (3)
C22	0.2032 (2)	0.22706 (8)	0.23517 (10)	0.0562 (4)
C23	0.0262 (2)	0.22827 (9)	0.17545 (11)	0.0642 (4)
C24	−0.11786 (19)	0.18160 (8)	0.19783 (11)	0.0571 (4)
C25	−0.09381 (19)	0.13336 (7)	0.27609 (11)	0.0551 (4)
C26	0.08443 (18)	0.13216 (7)	0.33465 (10)	0.0500 (3)
C41	0.7816 (2)	0.07173 (10)	0.53699 (14)	0.0737 (5)
C51	0.8802 (2)	0.24892 (9)	0.50026 (13)	0.0651 (5)
C17B	0.898 (2)	0.4240 (10)	0.2150 (14)	0.0874 (9)	0.197 (4)
C18B	0.135 (2)	0.5285 (8)	0.3807 (13)	0.0865 (12)	0.197 (4)
O13B	0.7483 (14)	0.4621 (5)	0.2658 (7)	0.0748 (6)	0.197 (4)
O15B	0.1779 (16)	0.4481 (5)	0.4134 (10)	0.0728 (6)	0.197 (4)
F4B	−0.253 (3)	0.2120 (13)	0.1380 (16)	0.0827 (4)	0.071 (4)
H16	0.30133	0.32452	0.45545	0.0602*
H17A	0.94989	0.40279	0.23819	0.1309*	0.803 (4)
H12	0.73740	0.31646	0.29069	0.0639*
H14	0.44718	0.50951	0.31489	0.0771*
H22	0.30229	0.25856	0.22119	0.0675*
H23	0.00548	0.26006	0.12131	0.0770*
H25	−0.19419	0.10232	0.28952	0.0662*
H26	0.10444	0.09926	0.38765	0.0600*
H41A	0.86731	0.04817	0.49709	0.1106*
H41B	0.69719	0.03475	0.55904	0.1106*
H41C	0.85625	0.09493	0.59293	0.1106*
H51A	0.96450	0.22046	0.54767	0.0976*
H51B	0.83938	0.29349	0.53081	0.0976*
H51C	0.94812	0.26244	0.44646	0.0976*
H17B	0.91718	0.45800	0.14857	0.1309*	0.803 (4)
H17C	0.80126	0.38258	0.14554	0.1309*	0.803 (4)
H18A	0.29026	0.56430	0.44132	0.1298*	0.803 (4)
H18B	0.06803	0.55363	0.44518	0.1298*	0.803 (4)
H18C	0.15032	0.54600	0.34477	0.1298*	0.803 (4)
H17D	0.99679	0.40337	0.26325	0.1309*	0.197 (4)
H17E	0.95528	0.45968	0.17517	0.1309*	0.197 (4)
H17F	0.83856	0.38452	0.17401	0.1309*	0.197 (4)
H18D	0.25069	0.55810	0.39539	0.1298*	0.197 (4)
H18E	0.03553	0.54860	0.41504	0.1298*	0.197 (4)
H18F	0.09270	0.52961	0.31114	0.1298*	0.197 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F4A	0.0562 (6)	0.1013 (10)	0.0835 (6)	0.0048 (5)	−0.0161 (5)	−0.0034 (7)
O13A	0.0855 (9)	0.0547 (6)	0.0943 (13)	0.0053 (6)	0.0491 (9)	0.0201 (8)
O15A	0.0821 (9)	0.0435 (8)	0.1025 (12)	0.0134 (6)	0.0473 (8)	0.0021 (7)
N1	0.0446 (4)	0.0365 (4)	0.0546 (5)	−0.0007 (3)	0.0076 (4)	−0.0003 (4)
N3	0.0490 (5)	0.0410 (5)	0.0638 (6)	0.0016 (4)	0.0079 (4)	0.0075 (4)
C2	0.0466 (5)	0.0357 (5)	0.0523 (6)	−0.0006 (4)	0.0092 (4)	0.0016 (4)
C4	0.0472 (5)	0.0477 (6)	0.0594 (7)	0.0056 (5)	0.0090 (5)	0.0059 (5)
C5	0.0443 (5)	0.0474 (6)	0.0564 (6)	0.0030 (4)	0.0075 (4)	−0.0035 (5)
C11	0.0481 (5)	0.0349 (5)	0.0552 (6)	−0.0017 (4)	0.0086 (4)	−0.0018 (4)
C12	0.0532 (6)	0.0419 (6)	0.0685 (8)	0.0010 (5)	0.0218 (5)	−0.0016 (5)
C13	0.0636 (7)	0.0450 (6)	0.0767 (9)	−0.0020 (5)	0.0287 (6)	0.0070 (6)
C14	0.0749 (8)	0.0362 (6)	0.0872 (10)	0.0049 (5)	0.0309 (7)	0.0091 (6)
C15	0.0604 (7)	0.0421 (6)	0.0707 (8)	0.0061 (5)	0.0237 (6)	−0.0004 (5)
C16	0.0528 (6)	0.0414 (6)	0.0589 (7)	−0.0013 (5)	0.0168 (5)	0.0020 (5)
C17A	0.0810 (14)	0.0824 (12)	0.110 (2)	0.0107 (12)	0.0532 (13)	0.0286 (14)
C18A	0.0976 (16)	0.0484 (10)	0.123 (3)	0.0222 (10)	0.0493 (15)	0.0015 (12)
C21	0.0472 (5)	0.0360 (5)	0.0510 (6)	0.0010 (4)	0.0080 (4)	−0.0026 (4)
C22	0.0589 (7)	0.0536 (7)	0.0559 (7)	−0.0060 (5)	0.0070 (5)	0.0071 (6)
C23	0.0724 (8)	0.0631 (8)	0.0545 (7)	0.0051 (6)	−0.0003 (6)	0.0091 (6)
C24	0.0488 (6)	0.0609 (8)	0.0592 (7)	0.0081 (5)	−0.0011 (5)	−0.0104 (6)
C25	0.0484 (6)	0.0497 (6)	0.0677 (8)	−0.0033 (5)	0.0094 (5)	−0.0097 (6)
C26	0.0531 (6)	0.0394 (5)	0.0575 (7)	−0.0017 (5)	0.0077 (5)	0.0014 (5)
C41	0.0584 (7)	0.0687 (9)	0.0917 (11)	0.0116 (7)	0.0019 (7)	0.0249 (8)
C51	0.0499 (6)	0.0632 (8)	0.0799 (10)	−0.0034 (6)	0.0008 (6)	−0.0123 (7)
C17B	0.0810 (14)	0.0824 (12)	0.110 (2)	0.0107 (12)	0.0532 (13)	0.0286 (14)
C18B	0.0976 (16)	0.0484 (10)	0.123 (3)	0.0222 (10)	0.0493 (15)	0.0015 (12)
O13B	0.0855 (9)	0.0547 (6)	0.0943 (13)	0.0053 (6)	0.0491 (9)	0.0201 (8)
O15B	0.0821 (9)	0.0435 (8)	0.1025 (12)	0.0134 (6)	0.0473 (8)	0.0021 (7)
F4B	0.0562 (6)	0.1013 (10)	0.0835 (6)	0.0048 (5)	−0.0161 (5)	−0.0034 (7)

Geometric parameters (Å, º) top

F4A—C24	1.3683 (19)	C23—C24	1.371 (2)
F4B—C24	1.28 (2)	C24—C25	1.368 (2)
O13A—C17A	1.394 (4)	C25—C26	1.3838 (19)
O13A—C13	1.383 (3)	C12—H12	0.9300
O13B—C17B	1.494 (19)	C14—H14	0.9300
O13B—C13	1.329 (10)	C16—H16	0.9300
O15A—C15	1.372 (3)	C17A—H17A	0.9600
O15A—C18A	1.414 (3)	C17A—H17B	0.9600
O15B—C15	1.349 (11)	C17A—H17C	0.9600
O15B—C18B	1.521 (17)	C17B—H17F	0.9600
N1—C2	1.3714 (14)	C17B—H17E	0.9600
N1—C5	1.3898 (16)	C17B—H17D	0.9600
N1—C11	1.4379 (14)	C18A—H18C	0.9600
N3—C4	1.3780 (17)	C18A—H18B	0.9600
N3—C2	1.3167 (16)	C18A—H18A	0.9600
C2—C21	1.4725 (16)	C18B—H18F	0.9600
C4—C5	1.3623 (18)	C18B—H18E	0.9600
C4—C41	1.495 (2)	C18B—H18D	0.9600
C5—C51	1.4889 (19)	C22—H22	0.9300
C11—C16	1.3740 (17)	C23—H23	0.9300
C11—C12	1.3909 (18)	C25—H25	0.9300
C12—C13	1.3870 (19)	C26—H26	0.9300
C13—C14	1.392 (2)	C41—H41B	0.9600
C14—C15	1.378 (2)	C41—H41A	0.9600
C15—C16	1.3990 (18)	C41—H41C	0.9600
C21—C22	1.3892 (18)	C51—H51C	0.9600
C21—C26	1.3936 (17)	C51—H51A	0.9600
C22—C23	1.384 (2)	C51—H51B	0.9600

C13—O13A—C17A	119.0 (2)	C15—C14—H14	120.00
C13—O13B—C17B	116.3 (9)	C11—C16—H16	121.00
C15—O15A—C18A	118.9 (2)	C15—C16—H16	121.00
C15—O15B—C18B	112.1 (9)	O13A—C17A—H17A	109.00
C5—N1—C11	124.89 (10)	O13A—C17A—H17B	110.00
C2—N1—C5	106.66 (9)	O13A—C17A—H17C	109.00
C2—N1—C11	127.70 (10)	H17A—C17A—H17B	110.00
C2—N3—C4	106.08 (10)	H17A—C17A—H17C	109.00
N1—C2—C21	125.18 (10)	H17B—C17A—H17C	109.00
N3—C2—C21	123.61 (10)	H17E—C17B—H17F	109.00
N1—C2—N3	111.20 (10)	H17D—C17B—H17F	109.00
C5—C4—C41	128.92 (12)	O13B—C17B—H17E	109.00
N3—C4—C5	110.28 (11)	O13B—C17B—H17F	110.00
N3—C4—C41	120.78 (12)	O13B—C17B—H17D	109.00
C4—C5—C51	131.59 (12)	H17D—C17B—H17E	109.00
N1—C5—C51	122.63 (11)	O15A—C18A—H18C	109.00
N1—C5—C4	105.78 (10)	H18A—C18A—H18B	109.00
N1—C11—C16	119.05 (10)	O15A—C18A—H18B	109.00
C12—C11—C16	122.28 (11)	O15A—C18A—H18A	109.00
N1—C11—C12	118.67 (10)	H18A—C18A—H18C	109.00
C11—C12—C13	117.85 (12)	H18B—C18A—H18C	109.00
O13A—C13—C14	114.49 (14)	O15B—C18B—H18D	109.00
O13A—C13—C12	124.31 (14)	H18E—C18B—H18F	110.00
O13B—C13—C14	112.9 (4)	H18D—C18B—H18F	109.00
C12—C13—C14	121.10 (13)	O15B—C18B—H18E	110.00
O13B—C13—C12	122.2 (4)	O15B—C18B—H18F	110.00
C13—C14—C15	119.66 (12)	H18D—C18B—H18E	109.00
C14—C15—C16	120.34 (12)	C21—C22—H22	120.00
O15A—C15—C14	123.67 (14)	C23—C22—H22	120.00
O15A—C15—C16	115.94 (14)	C24—C23—H23	121.00
O15B—C15—C16	110.8 (4)	C22—C23—H23	121.00
O15B—C15—C14	127.3 (5)	C24—C25—H25	121.00
C11—C16—C15	118.77 (12)	C26—C25—H25	121.00
C2—C21—C26	118.14 (11)	C21—C26—H26	119.00
C2—C21—C22	123.28 (11)	C25—C26—H26	119.00
C22—C21—C26	118.55 (11)	C4—C41—H41B	109.00
C21—C22—C23	120.72 (13)	C4—C41—H41C	109.00
C22—C23—C24	118.57 (14)	H41A—C41—H41B	109.00
C23—C24—C25	122.89 (13)	C4—C41—H41A	109.00
F4B—C24—C23	95.5 (10)	H41A—C41—H41C	109.00
F4B—C24—C25	140.3 (10)	H41B—C41—H41C	109.00
F4A—C24—C25	117.94 (13)	H51B—C51—H51C	109.00
F4A—C24—C23	119.18 (14)	H51A—C51—H51B	109.00
C24—C25—C26	117.98 (12)	H51A—C51—H51C	109.00
C21—C26—C25	121.28 (12)	C5—C51—H51A	109.00
C11—C12—H12	121.00	C5—C51—H51B	109.00
C13—C12—H12	121.00	C5—C51—H51C	109.00
C13—C14—H14	120.00

C17A—O13A—C13—C14	−179.4 (2)	C41—C4—C5—N1	178.65 (14)
C17A—O13A—C13—C12	−3.0 (3)	N3—C4—C5—C51	−179.23 (14)
C18A—O15A—C15—C14	−0.6 (3)	C41—C4—C5—C51	−1.1 (3)
C18A—O15A—C15—C16	176.7 (2)	C16—C11—C12—C13	−0.2 (2)
C2—N1—C5—C4	−0.21 (14)	N1—C11—C16—C15	−179.31 (12)
C11—N1—C2—N3	−170.50 (11)	C12—C11—C16—C15	0.7 (2)
C11—N1—C2—C21	10.84 (19)	N1—C11—C12—C13	179.83 (12)
C11—N1—C5—C51	−9.77 (19)	C11—C12—C13—C14	0.1 (2)
C5—N1—C2—C21	−178.82 (11)	C11—C12—C13—O13A	−176.12 (16)
C2—N1—C11—C16	60.35 (17)	O13A—C13—C14—C15	176.05 (16)
C5—N1—C11—C12	71.66 (16)	C12—C13—C14—C15	−0.5 (2)
C5—N1—C11—C16	−108.35 (14)	C13—C14—C15—C16	1.0 (2)
C2—N1—C11—C12	−119.64 (14)	C13—C14—C15—O15A	178.23 (18)
C5—N1—C2—N3	−0.15 (14)	O15A—C15—C16—C11	−178.53 (15)
C2—N1—C5—C51	179.54 (12)	C14—C15—C16—C11	−1.1 (2)
C11—N1—C5—C4	170.48 (11)	C2—C21—C22—C23	178.55 (12)
C4—N3—C2—N1	0.45 (14)	C26—C21—C22—C23	0.6 (2)
C2—N3—C4—C41	−178.92 (13)	C2—C21—C26—C25	−179.31 (12)
C2—N3—C4—C5	−0.59 (15)	C22—C21—C26—C25	−1.22 (19)
C4—N3—C2—C21	179.14 (11)	C21—C22—C23—C24	0.3 (2)
N1—C2—C21—C26	−151.86 (12)	C22—C23—C24—F4A	179.31 (14)
N3—C2—C21—C22	−148.36 (13)	C22—C23—C24—C25	−0.6 (2)
N3—C2—C21—C26	29.64 (18)	F4A—C24—C25—C26	−179.94 (14)
N1—C2—C21—C22	30.15 (19)	C23—C24—C25—C26	0.0 (2)
N3—C4—C5—N1	0.50 (15)	C24—C25—C26—C21	0.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C2/N3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cg1ⁱ	0.93	2.99	3.8714 (16)	159

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FN₂O₂
M_r	326.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	6.9654 (1), 17.8520 (3), 13.7121 (3)
β (°)	97.833 (2)
V (Å³)	1689.14 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.47 × 0.38 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan CrysAlis PRO (Oxford Diffraction, 2010)
T_min, T_max	0.558, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7744, 3533, 2723
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.138, 1.06
No. of reflections	3533
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C2/N3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cg1ⁱ	0.93	2.99	3.8714 (16)	159

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

JJ is thankful to the Department of Science and Technology [No. SR/S1/IC-07/2007] and the University Grants Commission [F. No. 36–21/2008 (SR)] for providing funding for this research work. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Banfi, E., Scialino, G., Zampieri, D., Mamolo, M. G., Vio, L., Ferrone, M., Fermeglia, M., Paneni, M. S. & Pricl, S. (2006). J. Antimicrob. Chemother. 58, 76–84. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 68| Part 2| February 2012| Page o256

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