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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1496–o1497.
Published online 2008 July 16. doi:  10.1107/S1600536808021326
PMCID: PMC2962126

1-[2-(4-Fluoro­benz­yloxy)-2-phenyl­ethyl]-1H-benzimidazole

Abstract

The asymmetric unit of the title compound, C22H19FN2O, contains two independent mol­ecules. The planar benzimidazole ring systems are oriented with respect to the phen­yl/fluoro­benzene rings at dihedral angles of 31.10 (4)/45.17 (5) and 45.52 (5)/68.63 (5)°, respectively, for the two mol­ecules. In the crystal structure, inter­molecular C—H(...)N and inter­molecular C—H(...)N and C—H(...)F hydrogen bonds link the mol­ecules into a three-dimensional network. There are C—H(...)π contacts between the benzimidazole and fluoro­benzene rings and a π–π contact between the benzimidazole and phenyl ring systems [centroid–centroid distance = 4.575 (1) Å].

Related literature

For general background, see: Brammer & Feczko (1988 [triangle]); Özel Güven et al. (2007a [triangle],b [triangle]). For related literature, see: Song & Shin (1998 [triangle]); Freer et al. (1986 [triangle]); Peeters et al. (1979a [triangle],b [triangle], 1996 [triangle]); Caira et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1496-scheme1.jpg

Experimental

Crystal data

  • C22H19FN2O
  • M r = 346.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1496-efi1.jpg
  • a = 12.6946 (2) Å
  • b = 18.1279 (4) Å
  • c = 15.3547 (3) Å
  • β = 95.747 (1)°
  • V = 3515.76 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 120 (2) K
  • 0.55 × 0.15 × 0.14 mm

Data collection

  • Bruker–Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.953, T max = 0.988
  • 41740 measured reflections
  • 8050 independent reflections
  • 5679 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.142
  • S = 1.07
  • 8050 reflections
  • 622 parameters
  • All H-atom parameters refined
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021326/xu2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021326/xu2436Isup2.hkl

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

Acknowledgments

The authors acknowledge Zonguldak Karaelmas University Research Fund (grant No. 2004–13-02–16).

supplementary crystallographic information

Comment

In recent years, there has been increasing interest in synthesis of heterocyclic compounds having biological and commercial importances. Clotrimazole (Song & Shin, 1998), econazole (Freer et al., 1986), ketoconazole (Peeters et al., 1979a) and miconazole (Peeters et al., 1979b) are well known imidazole ring containing, while itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) are 1H-1,2,4-triazole ring containing, azole derivatives. They have been developed for clinical uses as antifungal agents (Brammer & Feczko, 1988). Lately, similar structures to miconazole and econazole have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). In these structures, benzimidazole ring has been found in place of the imidazole ring of miconazole and econazole. We report herein the crystal structure of title benzimidazole derivative.

The asymmetric unit of the title compound (Fig. 1) contains two independent molecules, in which the bond lengths and angles are generally within normal ranges. The planar benzimidazole ring systems are oriented with respect to the phenyl and fluorobenzene rings at dihedral angles of 31.10 (4)°, 45.17 (5)° and 45.52 (5)°, 68.63 (5)° for unprimed and primed molecules, respectively. Atoms C8, C9, C16 and C8', C9', C16' are -0.105 (2), 0.065 (2), -0.060 (2) and -0.163 (2), -0.088 (2), 0.009 (2) Å away from the ring planes of the corresponding benzimidazole, phenyl and fluorobenzene, respectively. So, they are nearly coplanar with the attached rings.

In the crystal structure, intramolecular C—H···N and intermolecular C—H···N and C—H···F hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The C—H···π contacts (Table 1) between the benzimidazole and the fluorobenzene rings and a π-π contact between the benzimidazole and phenyl ring systems Cg1···Cg6i[symmetry code: (i) 1 - x, 1/2 + y, 1/2 - z, where Cg1 and Cg6 are centroids of the rings (N1/N2/C1/C2/C7) and (C10'-C15'), respectively] further stabilize the structure, with centroid-centroid distance of 4.575 (1) Å.

Experimental

The title compound was synthesized by the reaction of 2-(1H-benzimidazol-1-yl) -1-phenylethanol (Özel Güven et al., 2007a) with NaH and appropriate benzyl halide. A solution of alcohol (300 mg, 1.259 mmol) in DMF (2.4 ml) was added to NaH (63 mg, 1.574 mmol) in small fractions. The appropriate benzyl halide (238 mg, 1.259 mmol) in DMF (1.2 ml) was added dropwise. The mixture was stirred at room temperature for 2 h, and the excess hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using chloroform-methanol as eluent. Crystals suitable for X-ray analysis were obtained by the recrystallization of the ether from a mixture of hexane/ethyl acetate (1:2) (yield; 364 mg, 83%).

Refinement

H atoms were located in difference syntheses and refined isotropically [C—H = 0.94 (2)–1.05 (2) Å; Uiso(H) = 0.023 (5)–0.051 (6) Å2].

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as double dashed line.
Fig. 2.
A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C22H19FN2OF000 = 1456
Mr = 346.39Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8094 reflections
a = 12.6946 (2) Åθ = 2.9–27.5º
b = 18.1279 (4) ŵ = 0.09 mm1
c = 15.3547 (3) ÅT = 120 (2) K
β = 95.747 (1)ºRod-shaped, colorless
V = 3515.76 (12) Å30.55 × 0.15 × 0.14 mm
Z = 8

Data collection

Bruker–Nonius KappaCCD diffractometer8050 independent reflections
Radiation source: fine-focus sealed tube5679 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.065
Detector resolution: 9.091 pixels mm-1θmax = 27.5º
T = 120(2) Kθmin = 3.0º
[var phi] and ω scansh = −16→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)k = −23→23
Tmin = 0.953, Tmax = 0.988l = −19→19
41740 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.055  w = 1/[σ2(Fo2) + (0.0671P)2 + 0.7368P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.43 e Å3
8050 reflectionsΔρmin = −0.43 e Å3
622 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0237 (14)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
F1.32492 (8)0.12305 (7)1.08865 (8)0.0437 (3)
O0.89904 (9)0.13207 (7)0.84616 (8)0.0271 (3)
N10.83956 (11)0.19499 (8)0.67743 (9)0.0249 (3)
N20.98761 (11)0.20522 (9)0.61001 (10)0.0288 (4)
C10.94433 (14)0.21182 (11)0.68318 (12)0.0289 (4)
H10.9829 (14)0.2262 (11)0.7390 (12)0.027 (5)*
C20.90500 (13)0.18153 (9)0.54985 (11)0.0236 (4)
C30.90444 (14)0.16519 (10)0.46108 (12)0.0280 (4)
H30.9686 (16)0.1703 (12)0.4301 (13)0.038 (6)*
C40.81070 (14)0.14160 (10)0.41732 (12)0.0292 (4)
H40.8070 (16)0.1292 (12)0.3561 (15)0.039 (6)*
C50.71803 (14)0.13502 (10)0.45929 (12)0.0283 (4)
H50.6542 (15)0.1181 (11)0.4275 (13)0.030 (5)*
C60.71679 (13)0.15155 (10)0.54705 (12)0.0255 (4)
H60.6538 (16)0.1488 (12)0.5780 (13)0.036 (5)*
C70.81188 (13)0.17443 (9)0.59110 (11)0.0227 (4)
C80.77179 (14)0.19141 (11)0.74888 (12)0.0274 (4)
H810.7859 (15)0.2378 (13)0.7864 (13)0.037 (6)*
H820.6946 (16)0.1908 (11)0.7251 (13)0.032 (5)*
C90.79393 (13)0.12350 (10)0.80559 (11)0.0257 (4)
H90.7892 (14)0.0767 (12)0.7672 (13)0.030 (5)*
C100.71281 (13)0.11680 (10)0.87108 (11)0.0239 (4)
C110.63294 (14)0.06463 (11)0.85919 (12)0.0275 (4)
H110.6307 (14)0.0317 (12)0.8102 (13)0.030 (5)*
C120.55543 (14)0.06074 (11)0.91698 (12)0.0294 (4)
H120.5013 (16)0.0250 (12)0.9071 (13)0.036 (5)*
C130.55847 (14)0.10849 (11)0.98734 (12)0.0302 (4)
H130.5027 (16)0.1064 (11)1.0291 (13)0.034 (5)*
C140.63851 (14)0.16059 (11)0.99970 (12)0.0300 (4)
H140.6394 (16)0.1942 (13)1.0485 (14)0.042 (6)*
C150.71528 (14)0.16487 (10)0.94216 (12)0.0277 (4)
H150.7732 (15)0.2003 (11)0.9511 (12)0.028 (5)*
C160.93679 (14)0.06654 (11)0.89152 (13)0.0294 (4)
H1610.9424 (17)0.0256 (14)0.8473 (15)0.048 (6)*
H1620.8831 (15)0.0495 (11)0.9330 (13)0.030 (5)*
C171.04175 (13)0.08265 (10)0.94178 (11)0.0259 (4)
C181.05046 (14)0.13885 (11)1.00380 (12)0.0301 (4)
H180.9877 (18)0.1682 (13)1.0149 (14)0.048 (6)*
C191.14550 (15)0.15275 (11)1.05316 (13)0.0323 (4)
H191.1513 (16)0.1897 (13)1.0964 (14)0.038 (6)*
C201.23161 (14)0.10960 (11)1.03963 (12)0.0297 (4)
C211.22666 (15)0.05391 (11)0.97882 (12)0.0317 (4)
H211.2875 (16)0.0263 (12)0.9714 (13)0.037 (6)*
C221.13085 (14)0.04091 (11)0.92987 (12)0.0295 (4)
H221.1258 (15)−0.0001 (12)0.8881 (14)0.036 (5)*
F'0.72117 (9)0.07392 (7)0.18637 (7)0.0422 (3)
O'0.35374 (9)0.09943 (7)0.42429 (9)0.0319 (3)
N1'0.32870 (11)0.19095 (8)0.57339 (9)0.0250 (3)
N2'0.49161 (11)0.21227 (8)0.63993 (10)0.0274 (3)
C1'0.43292 (13)0.20470 (10)0.56517 (12)0.0265 (4)
H1A0.4581 (15)0.2084 (11)0.5054 (13)0.033 (5)*
C2'0.42077 (13)0.20278 (9)0.70299 (12)0.0242 (4)
C3'0.43907 (14)0.20280 (10)0.79409 (12)0.0277 (4)
H3A0.5121 (16)0.2104 (11)0.8237 (13)0.035 (5)*
C4'0.35328 (14)0.19125 (11)0.84097 (12)0.0290 (4)
H4A0.3623 (15)0.1912 (11)0.9025 (14)0.034 (5)*
C5'0.25116 (14)0.18014 (10)0.79938 (12)0.0284 (4)
H5A0.1897 (14)0.1719 (10)0.8350 (12)0.023 (5)*
C6'0.23161 (13)0.17905 (10)0.70912 (12)0.0252 (4)
H6A0.1612 (15)0.1685 (11)0.6825 (12)0.029 (5)*
C7'0.31895 (13)0.18983 (9)0.66247 (11)0.0234 (4)
C8'0.24572 (14)0.17291 (10)0.50377 (12)0.0267 (4)
H8A0.2466 (15)0.2088 (12)0.4553 (13)0.034 (5)*
H8B0.1797 (16)0.1747 (12)0.5281 (13)0.034 (5)*
C9'0.25876 (14)0.09658 (10)0.46651 (12)0.0282 (4)
H9A0.2690 (15)0.0595 (12)0.5175 (13)0.033 (5)*
C10'0.16396 (13)0.07542 (10)0.40381 (12)0.0278 (4)
C11'0.10205 (14)0.01572 (11)0.42324 (13)0.0311 (4)
H11A0.1273 (17)−0.0142 (13)0.4771 (15)0.046 (6)*
C12'0.01201 (15)−0.00234 (12)0.36915 (13)0.0356 (5)
H12A−0.0308 (18)−0.0463 (14)0.3827 (15)0.051 (6)*
C13'−0.01693 (15)0.03929 (12)0.29548 (13)0.0367 (5)
H13A−0.0804 (18)0.0252 (13)0.2610 (14)0.045 (6)*
C14'0.04507 (16)0.09780 (12)0.27391 (13)0.0380 (5)
H14A0.0274 (17)0.1268 (13)0.2198 (15)0.046 (6)*
C15'0.13594 (16)0.11604 (12)0.32758 (13)0.0334 (4)
H15A0.1795 (16)0.1575 (13)0.3127 (14)0.042 (6)*
C16'0.38651 (15)0.02982 (11)0.39365 (14)0.0313 (4)
H16A0.3236 (17)0.0054 (12)0.3565 (14)0.041 (6)*
H16B0.4113 (16)−0.0028 (13)0.4487 (14)0.041 (6)*
C17'0.47598 (13)0.04194 (10)0.33826 (11)0.0263 (4)
C18'0.47972 (15)0.10525 (11)0.28687 (12)0.0295 (4)
H18A0.4234 (15)0.1408 (12)0.2871 (13)0.031 (5)*
C19'0.56238 (15)0.11670 (11)0.23553 (12)0.0316 (4)
H19A0.5682 (16)0.1634 (13)0.2001 (14)0.040 (6)*
C20'0.63892 (14)0.06312 (11)0.23568 (12)0.0295 (4)
C21'0.63728 (15)−0.00091 (11)0.28360 (13)0.0330 (4)
H21A0.6947 (18)−0.0365 (14)0.2804 (14)0.049 (6)*
C22'0.55530 (14)−0.01061 (11)0.33574 (12)0.0300 (4)
H22A0.5502 (16)−0.0561 (13)0.3701 (14)0.039 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F0.0279 (6)0.0494 (8)0.0519 (7)−0.0033 (5)−0.0053 (5)0.0001 (6)
O0.0248 (6)0.0294 (7)0.0266 (6)0.0005 (5)0.0007 (5)0.0048 (5)
N10.0223 (7)0.0297 (8)0.0225 (7)−0.0015 (6)0.0014 (6)0.0024 (6)
N20.0240 (7)0.0334 (9)0.0287 (8)−0.0050 (6)0.0007 (6)0.0060 (7)
C10.0260 (9)0.0331 (11)0.0269 (10)−0.0049 (7)−0.0012 (8)0.0041 (8)
C20.0214 (8)0.0222 (9)0.0272 (9)−0.0001 (7)0.0019 (7)0.0047 (7)
C30.0272 (9)0.0295 (10)0.0281 (10)0.0026 (8)0.0073 (7)0.0052 (8)
C40.0342 (10)0.0290 (10)0.0244 (9)0.0038 (8)0.0024 (7)−0.0012 (8)
C50.0266 (9)0.0277 (10)0.0295 (10)−0.0008 (7)−0.0022 (7)−0.0001 (8)
C60.0223 (8)0.0254 (9)0.0286 (9)−0.0003 (7)0.0025 (7)0.0022 (7)
C70.0248 (8)0.0220 (9)0.0212 (8)0.0021 (7)0.0017 (7)0.0027 (7)
C80.0262 (9)0.0321 (10)0.0241 (9)0.0010 (8)0.0045 (7)0.0021 (8)
C90.0237 (9)0.0295 (10)0.0235 (9)0.0007 (7)0.0013 (7)0.0003 (8)
C100.0223 (8)0.0270 (9)0.0221 (9)0.0022 (7)0.0010 (6)0.0026 (7)
C110.0292 (9)0.0285 (10)0.0242 (9)−0.0014 (7)−0.0004 (7)0.0001 (8)
C120.0238 (9)0.0318 (10)0.0318 (10)−0.0051 (8)−0.0010 (7)0.0077 (8)
C130.0271 (9)0.0342 (11)0.0297 (10)0.0036 (8)0.0054 (8)0.0082 (8)
C140.0323 (10)0.0306 (10)0.0279 (10)0.0013 (8)0.0069 (8)0.0010 (8)
C150.0285 (9)0.0269 (10)0.0277 (9)−0.0036 (8)0.0026 (7)0.0003 (8)
C160.0293 (9)0.0268 (10)0.0315 (10)0.0040 (7)0.0006 (8)0.0030 (8)
C170.0269 (9)0.0259 (9)0.0252 (9)0.0017 (7)0.0045 (7)0.0053 (7)
C180.0280 (9)0.0291 (10)0.0340 (10)0.0032 (8)0.0065 (8)−0.0001 (8)
C190.0344 (10)0.0299 (11)0.0326 (10)−0.0023 (8)0.0029 (8)−0.0018 (9)
C200.0236 (9)0.0330 (10)0.0319 (10)−0.0035 (8)−0.0003 (7)0.0071 (8)
C210.0285 (9)0.0352 (11)0.0322 (10)0.0083 (8)0.0072 (8)0.0070 (8)
C220.0343 (10)0.0318 (10)0.0224 (9)0.0069 (8)0.0039 (7)0.0034 (8)
F'0.0391 (6)0.0524 (8)0.0372 (6)0.0111 (5)0.0142 (5)0.0048 (6)
O'0.0283 (7)0.0285 (7)0.0400 (8)−0.0007 (5)0.0087 (6)−0.0077 (6)
N1'0.0237 (7)0.0277 (8)0.0237 (8)−0.0014 (6)0.0032 (6)−0.0005 (6)
N2'0.0243 (7)0.0276 (8)0.0307 (8)−0.0024 (6)0.0043 (6)−0.0004 (6)
C1'0.0255 (9)0.0256 (9)0.0289 (10)−0.0011 (7)0.0056 (7)−0.0002 (7)
C2'0.0235 (8)0.0197 (9)0.0296 (9)0.0003 (7)0.0034 (7)−0.0005 (7)
C3'0.0257 (9)0.0253 (10)0.0310 (10)0.0012 (7)−0.0018 (7)−0.0015 (8)
C4'0.0329 (10)0.0288 (10)0.0251 (10)0.0055 (8)0.0020 (8)0.0003 (8)
C5'0.0282 (9)0.0269 (10)0.0310 (10)0.0029 (7)0.0077 (8)0.0018 (8)
C6'0.0216 (8)0.0241 (9)0.0298 (10)0.0009 (7)0.0030 (7)−0.0016 (7)
C7'0.0250 (8)0.0191 (8)0.0261 (9)0.0026 (7)0.0020 (7)−0.0005 (7)
C8'0.0249 (9)0.0305 (10)0.0244 (9)−0.0005 (7)0.0007 (7)−0.0009 (8)
C9'0.0256 (9)0.0286 (10)0.0308 (10)−0.0014 (7)0.0041 (7)0.0003 (8)
C10'0.0265 (9)0.0299 (10)0.0269 (9)0.0031 (7)0.0023 (7)−0.0064 (8)
C11'0.0317 (10)0.0282 (10)0.0333 (10)0.0015 (8)0.0025 (8)−0.0043 (8)
C12'0.0332 (10)0.0344 (11)0.0399 (11)−0.0034 (9)0.0060 (8)−0.0106 (9)
C13'0.0291 (10)0.0464 (13)0.0337 (11)0.0032 (9)−0.0011 (8)−0.0144 (9)
C14'0.0444 (12)0.0448 (13)0.0241 (10)0.0092 (10)0.0001 (8)−0.0034 (9)
C15'0.0384 (11)0.0324 (11)0.0302 (10)−0.0002 (9)0.0074 (8)−0.0035 (8)
C16'0.0297 (9)0.0264 (10)0.0381 (11)0.0013 (8)0.0049 (8)−0.0026 (8)
C17'0.0263 (9)0.0253 (9)0.0265 (9)0.0006 (7)−0.0011 (7)−0.0049 (7)
C18'0.0295 (9)0.0300 (10)0.0286 (10)0.0074 (8)0.0011 (7)−0.0026 (8)
C19'0.0365 (10)0.0316 (11)0.0265 (10)0.0066 (8)0.0032 (8)0.0013 (8)
C20'0.0283 (9)0.0362 (11)0.0245 (9)0.0031 (8)0.0048 (7)−0.0029 (8)
C21'0.0323 (10)0.0306 (11)0.0359 (11)0.0080 (8)0.0028 (8)−0.0049 (8)
C22'0.0336 (10)0.0237 (10)0.0323 (10)0.0027 (8)0.0006 (8)−0.0013 (8)

Geometric parameters (Å, °)

F—C201.360 (2)F'—C20'1.364 (2)
O—C91.423 (2)O'—C9'1.426 (2)
O—C161.435 (2)O'—C16'1.423 (2)
N1—C11.359 (2)N1'—C1'1.365 (2)
N1—C71.388 (2)N1'—C7'1.386 (2)
N1—C81.462 (2)N1'—C8'1.461 (2)
N2—C11.305 (2)N2'—C1'1.312 (2)
N2—C21.394 (2)N2'—C2'1.397 (2)
C1—H10.980 (19)C1'—H1A1.00 (2)
C2—C31.394 (3)C2'—C7'1.397 (2)
C2—C71.402 (2)C3'—C2'1.395 (3)
C3—H30.99 (2)C3'—C4'1.380 (3)
C4—C31.375 (3)C3'—H3A1.00 (2)
C4—C51.402 (3)C4'—C5'1.401 (3)
C4—H40.96 (2)C4'—H4A0.94 (2)
C5—H50.95 (2)C5'—C6'1.383 (3)
C6—C51.382 (3)C5'—H5A1.008 (18)
C6—H60.97 (2)C6'—H6A0.964 (19)
C7—C61.387 (2)C7'—C6'1.393 (2)
C8—H811.03 (2)C8'—C9'1.513 (3)
C8—H821.011 (19)C8'—H8A0.99 (2)
C9—C81.518 (3)C8'—H8B0.95 (2)
C9—C101.514 (2)C9'—C10'1.513 (2)
C9—H91.03 (2)C9'—H9A1.03 (2)
C10—C151.395 (3)C10'—C11'1.387 (3)
C11—C101.385 (3)C10'—C15'1.398 (3)
C11—C121.391 (3)C11'—C12'1.383 (3)
C11—H110.96 (2)C11'—H11A1.01 (2)
C12—C131.382 (3)C12'—H12A1.00 (2)
C12—H120.95 (2)C13'—C12'1.379 (3)
C13—H131.00 (2)C13'—C14'1.381 (3)
C14—C131.386 (3)C13'—H13A0.95 (2)
C14—C151.382 (3)C14'—H14A0.99 (2)
C14—H140.97 (2)C15'—C14'1.389 (3)
C15—H150.97 (2)C15'—H15A0.97 (2)
C16—H1611.01 (2)C16'—H16A1.03 (2)
C16—H1621.03 (2)C16'—H16B1.05 (2)
C17—C161.500 (2)C17'—C16'1.502 (3)
C17—C181.391 (3)C17'—C18'1.396 (3)
C17—C221.388 (2)C17'—C22'1.389 (3)
C18—C191.382 (3)C18'—C19'1.390 (3)
C18—H180.99 (2)C18'—H18A0.96 (2)
C19—H190.94 (2)C19'—H19A1.01 (2)
C20—C191.377 (3)C20'—C19'1.374 (3)
C20—C211.372 (3)C20'—C21'1.376 (3)
C21—C221.384 (3)C21'—C22'1.386 (3)
C21—H210.94 (2)C21'—H21A0.98 (2)
C22—H220.98 (2)C22'—H22A0.98 (2)
C9—O—C16112.02 (13)C16'—O'—C9'113.99 (14)
C1—N1—C7105.96 (14)C1'—N1'—C7'106.09 (14)
C1—N1—C8127.37 (15)C1'—N1'—C8'127.44 (15)
C7—N1—C8126.37 (14)C7'—N1'—C8'126.15 (14)
C1—N2—C2104.19 (14)C1'—N2'—C2'104.19 (14)
N1—C1—H1121.1 (11)N1'—C1'—H1A119.8 (11)
N2—C1—N1114.66 (16)N2'—C1'—N1'114.16 (16)
N2—C1—H1124.2 (11)N2'—C1'—H1A126.0 (11)
N2—C2—C7109.96 (15)N2'—C2'—C7'110.07 (15)
C3—C2—N2130.02 (16)C3'—C2'—N2'129.88 (16)
C3—C2—C7120.02 (15)C3'—C2'—C7'120.03 (16)
C2—C3—H3121.8 (12)C2'—C3'—H3A120.6 (11)
C4—C3—C2117.60 (16)C4'—C3'—C2'117.52 (16)
C4—C3—H3120.6 (12)C4'—C3'—H3A121.8 (11)
C3—C4—C5121.79 (17)C3'—C4'—C5'121.77 (17)
C3—C4—H4120.3 (12)C3'—C4'—H4A120.1 (12)
C5—C4—H4117.9 (12)C5'—C4'—H4A118.2 (12)
C4—C5—H5120.1 (12)C4'—C5'—H5A120.3 (10)
C6—C5—C4121.45 (16)C6'—C5'—C4'121.58 (17)
C6—C5—H5118.5 (12)C6'—C5'—H5A118.1 (10)
C5—C6—C7116.49 (16)C5'—C6'—C7'116.17 (16)
C5—C6—H6123.8 (12)C5'—C6'—H6A119.6 (11)
C7—C6—H6119.7 (12)C7'—C6'—H6A124.2 (11)
N1—C7—C2105.22 (14)N1'—C7'—C6'131.61 (15)
C6—C7—N1132.15 (16)N1'—C7'—C2'105.49 (14)
C6—C7—C2122.63 (16)C6'—C7'—C2'122.90 (16)
N1—C8—C9112.17 (15)N1'—C8'—C9'112.54 (15)
N1—C8—H81107.6 (11)N1'—C8'—H8A110.0 (11)
N1—C8—H82110.6 (11)N1'—C8'—H8B107.7 (12)
C9—C8—H81109.3 (11)C9'—C8'—H8A107.9 (12)
C9—C8—H82108.4 (12)C9'—C8'—H8B108.2 (13)
H81—C8—H82108.7 (16)H8A—C8'—H8B110.5 (17)
O—C9—C8105.91 (14)O'—C9'—C8'105.57 (14)
O—C9—C10112.84 (14)O'—C9'—C10'112.01 (15)
O—C9—H9109.7 (10)O'—C9'—H9A108.7 (11)
C8—C9—H9110.0 (11)C8'—C9'—C10'111.24 (15)
C10—C9—C8110.29 (14)C8'—C9'—H9A108.7 (11)
C10—C9—H9108.0 (11)C10'—C9'—H9A110.4 (11)
C11—C10—C9120.31 (16)C11'—C10'—C15'119.25 (17)
C11—C10—C15119.24 (16)C11'—C10'—C9'119.50 (17)
C15—C10—C9120.40 (16)C15'—C10'—C9'121.22 (17)
C10—C11—C12120.38 (17)C10'—C11'—H11A117.0 (13)
C10—C11—H11119.5 (12)C12'—C11'—C10'120.49 (19)
C12—C11—H11120.1 (12)C12'—C11'—H11A122.5 (13)
C11—C12—H12118.8 (13)C11'—C12'—H12A119.9 (13)
C13—C12—C11120.05 (17)C13'—C12'—C11'120.0 (2)
C13—C12—H12121.2 (13)C13'—C12'—H12A120.1 (13)
C12—C13—C14119.77 (17)C12'—C13'—C14'120.38 (18)
C12—C13—H13120.6 (12)C12'—C13'—H13A116.8 (14)
C14—C13—H13119.6 (12)C14'—C13'—H13A122.8 (14)
C13—C14—H14119.2 (13)C13'—C14'—C15'120.01 (19)
C15—C14—C13120.33 (18)C13'—C14'—H14A121.5 (13)
C15—C14—H14120.5 (13)C15'—C14'—H14A118.5 (13)
C10—C15—H15118.6 (11)C10'—C15'—H15A120.0 (13)
C14—C15—C10120.22 (17)C14'—C15'—C10'119.85 (19)
C14—C15—H15121.2 (11)C14'—C15'—H15A120.1 (12)
O—C16—C17108.96 (15)O'—C16'—C17'108.67 (15)
O—C16—H161108.9 (13)O'—C16'—H16A109.1 (12)
O—C16—H162109.9 (11)O'—C16'—H16B107.8 (12)
C17—C16—H162110.5 (10)C17'—C16'—H16A109.7 (12)
C17—C16—H161111.6 (12)C17'—C16'—H16B110.8 (11)
H162—C16—H161106.9 (17)H16A—C16'—H16B110.7 (17)
C18—C17—C16120.02 (16)C18'—C17'—C16'120.72 (16)
C22—C17—C18118.64 (17)C22'—C17'—C18'118.82 (17)
C22—C17—C16121.30 (17)C22'—C17'—C16'120.45 (17)
C17—C18—H18120.2 (13)C17'—C18'—H18A118.8 (12)
C19—C18—C17120.93 (17)C19'—C18'—C17'120.91 (17)
C19—C18—H18118.8 (13)C19'—C18'—H18A120.3 (12)
C18—C19—H19121.3 (13)C18'—C19'—H19A121.9 (12)
C20—C19—C18118.45 (19)C20'—C19'—C18'117.87 (18)
C20—C19—H19120.2 (13)C20'—C19'—H19A120.2 (12)
F—C20—C19118.38 (17)F'—C20'—C19'118.57 (17)
F—C20—C21119.09 (16)F'—C20'—C21'118.13 (16)
C21—C20—C19122.53 (17)C19'—C20'—C21'123.30 (18)
C20—C21—C22118.19 (17)C20'—C21'—C22'117.92 (18)
C20—C21—H21119.6 (13)C20'—C21'—H21A118.6 (14)
C22—C21—H21122.2 (13)C22'—C21'—H21A123.5 (14)
C17—C22—H22119.9 (12)C17'—C22'—H22A118.2 (12)
C21—C22—C17121.26 (18)C21'—C22'—C17'121.14 (18)
C21—C22—H22118.8 (12)C21'—C22'—H22A120.6 (12)
C16—O—C9—C8−171.09 (14)C16'—O'—C9'—C8'172.99 (15)
C16—O—C9—C1068.15 (19)C16'—O'—C9'—C10'−65.8 (2)
C9—O—C16—C17−172.87 (14)C9'—O'—C16'—C17'170.86 (14)
C7—N1—C1—N20.7 (2)C7'—N1'—C1'—N2'0.3 (2)
C8—N1—C1—N2174.73 (17)C8'—N1'—C1'—N2'−173.60 (17)
C1—N1—C7—C2−0.70 (18)C1'—N1'—C7'—C6'179.34 (18)
C1—N1—C7—C6179.78 (19)C8'—N1'—C7'—C6'−6.7 (3)
C8—N1—C7—C2−174.84 (16)C1'—N1'—C7'—C2'−0.44 (18)
C8—N1—C7—C65.6 (3)C8'—N1'—C7'—C2'173.54 (16)
C1—N1—C8—C9−73.6 (2)C1'—N1'—C8'—C9'70.5 (2)
C7—N1—C8—C999.33 (19)C7'—N1'—C8'—C9'−102.2 (2)
C2—N2—C1—N1−0.3 (2)C2'—N2'—C1'—N1'0.0 (2)
C1—N2—C2—C3−179.88 (19)C1'—N2'—C2'—C3'177.92 (19)
C1—N2—C2—C7−0.15 (19)C1'—N2'—C2'—C7'−0.30 (19)
N2—C2—C3—C4179.03 (18)C3'—C2'—C7'—N1'−177.96 (16)
C7—C2—C3—C4−0.7 (3)N2'—C2'—C7'—N1'0.47 (19)
N2—C2—C7—N10.54 (19)C3'—C2'—C7'—C6'2.2 (3)
N2—C2—C7—C6−179.88 (16)N2'—C2'—C7'—C6'−179.33 (16)
C3—C2—C7—N1−179.70 (16)C4'—C3'—C2'—N2'−179.40 (17)
C3—C2—C7—C6−0.1 (3)C4'—C3'—C2'—C7'−1.3 (3)
C5—C4—C3—C20.9 (3)C2'—C3'—C4'—C5'−0.2 (3)
C3—C4—C5—C6−0.4 (3)C3'—C4'—C5'—C6'1.0 (3)
C7—C6—C5—C4−0.4 (3)C4'—C5'—C6'—C7'−0.2 (3)
N1—C7—C6—C5−179.90 (18)N1'—C7'—C6'—C5'178.82 (18)
C2—C7—C6—C50.6 (3)C2'—C7'—C6'—C5'−1.4 (3)
O—C9—C8—N165.00 (18)N1'—C8'—C9'—O'−66.22 (19)
C10—C9—C8—N1−172.60 (14)N1'—C8'—C9'—C10'172.07 (15)
O—C9—C10—C11−136.59 (17)O'—C9'—C10'—C11'125.14 (18)
O—C9—C10—C1545.8 (2)C8'—C9'—C10'—C11'−116.98 (19)
C8—C9—C10—C11105.18 (19)O'—C9'—C10'—C15'−56.5 (2)
C8—C9—C10—C15−72.4 (2)C8'—C9'—C10'—C15'61.4 (2)
C9—C10—C15—C14177.27 (16)C9'—C10'—C11'—C12'176.72 (17)
C11—C10—C15—C14−0.3 (3)C15'—C10'—C11'—C12'−1.7 (3)
C12—C11—C10—C9−176.91 (16)C9'—C10'—C15'—C14'−176.33 (17)
C12—C11—C10—C150.7 (3)C11'—C10'—C15'—C14'2.1 (3)
C10—C11—C12—C13−0.8 (3)C10'—C11'—C12'—C13'−0.2 (3)
C11—C12—C13—C140.5 (3)C14'—C13'—C12'—C11'1.8 (3)
C15—C14—C13—C12−0.1 (3)C12'—C13'—C14'—C15'−1.4 (3)
C13—C14—C15—C100.1 (3)C10'—C15'—C14'—C13'−0.5 (3)
C18—C17—C16—O57.8 (2)C18'—C17'—C16'—O'−33.7 (2)
C22—C17—C16—O−124.31 (18)C22'—C17'—C16'—O'147.83 (17)
C16—C17—C18—C19177.53 (17)C16'—C17'—C18'—C19'179.98 (17)
C22—C17—C18—C19−0.4 (3)C22'—C17'—C18'—C19'−1.5 (3)
C16—C17—C22—C21−177.36 (17)C18'—C17'—C22'—C21'0.2 (3)
C18—C17—C22—C210.6 (3)C16'—C17'—C22'—C21'178.70 (17)
C17—C18—C19—C20−0.1 (3)C17'—C18'—C19'—C20'1.3 (3)
F—C20—C19—C18−179.59 (16)F'—C20'—C19'—C18'−179.30 (16)
C21—C20—C19—C180.4 (3)C21'—C20'—C19'—C18'0.3 (3)
F—C20—C21—C22179.72 (16)F'—C20'—C21'—C22'178.03 (16)
C19—C20—C21—C22−0.3 (3)C19'—C20'—C21'—C22'−1.6 (3)
C20—C21—C22—C17−0.2 (3)C20'—C21'—C22'—C17'1.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···N2'0.97 (2)2.62 (2)3.498 (2)150.5 (17)
C6'—H6A···N2i0.964 (19)2.459 (19)3.345 (2)152.7 (16)
C13—H13···Fi1.00 (2)2.54 (2)3.493 (2)159.6 (16)
C19'—H19A···N2'ii1.01 (2)2.59 (2)3.509 (2)151.1 (16)
C5—H5···Cg8iii0.95 (2)2.662 (19)3.514 (2)149.0 (15)
C22'—H22A···Cg2iv0.98 (2)2.62 (9)3.518 (2)141.9 (16)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2436).

References

  • Brammer, K. W. & Feczko, J. M. (1988). In Antifungal Drugs, edited by V. St. Georgiev, pp. 561–563. New York Academy of Science.
  • Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci.93, 601–611. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350–1352.
  • Hooft, R. W. W. (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzimology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Özel Güven, Ö., Erdoğan, T., Göker, H. & Yıldız, S. (2007a). Bioorg. Med. Chem. Lett.17, 2233–2236. [PubMed]
  • Özel Güven, Ö., Erdoğan, T., Göker, H. & Yıldız, S. (2007b). J. Heterocycl. Chem.44, 731–734.
  • Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979a). Acta Cryst. B35, 2461–2464.
  • Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979b). Bull. Soc. Chim. Belg.88, 265–272.
  • Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1996). Acta Cryst. C52, 2225–2229.
  • Sheldrick, G. M. (2007). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, H. & Shin, H.-S. (1998). Acta Cryst. C54, 1675–1677. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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