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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 11| November 2013| Pages o1599-o1600

2-(2,4-Di­fluoro­phen­yl)-4,5-di­methyl-1-(4-methyl­phen­yl)-1H-imidazole monohydrate

aDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India, bDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, cDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and dLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
*Correspondence e-mail: raghema2000@yahoo.co.in

(Received 15 September 2013; accepted 24 September 2013; online 2 October 2013)

The asymmetric unit of the title compound, C18H16F2N2·H2O, contains two independent mol­ecules (A and B), and two independent water mol­ecules of crystallization. In mol­ecule A, the imidazole ring makes dihedral angles of 47.46 (7) and 60.98 (6)° with the 2,4-di­fluoro­phenyl and methyl­phenyl rings, respectively. The corresponding angles in mol­ecule B are 45.85 (7) and 62.78 (7)°, respectively. The dihedral angle between the two benzene rings is 64.98 (7)° in mol­ecule A and 65.53 (7)° in mol­ecule B. In the crystal, the two independent mol­ecules are linked by O—H⋯N and O—H⋯O hydrogen bonds, forming chains propagating along [100]. These chains are linked via C—H⋯F hydrogen bonds, forming slab-like two-dimensional networks lying parallel to (001).

Related literature

For background and the biological properties of imidazole derivatives, see: Dutta et al. (2009[Dutta, S., Mariappan, G., Roy, S. & Verma, M. (2009). Indian Drugs, 46, 50-53.]); Hori et al. (2000[Hori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60-64.]); Khabnadideh et al. (2003[Khabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863-2865.]); Mamolo et al. (2004[Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). ARKIVOC, v, 231-250.]); Quattara et al. (1987[Quattara, L., Debaert, M. & Cavier, R. (1987). Il Farmaco, 42, 449-456.]); Sengupta & Bhattacharya (1983[Sengupta, A. K. & Bhattacharya, T. (1983). J. Indian Chem. Soc. 60, 373-376.]); Ucucu et al. (2001[Ucucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285-290.]); Noilada et al. (2004[Noilada, A., Koyunoglu, S., Saygili, N., Kupeli, E., Noilada, E., Bedir, E. & Khan, I. (2004). Arch. Pharm. Pharm. Med. Chem. 337, 96-104.]). For related structures, see: Rizwana et al. (2013[Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.]); Gayathri et al. (2010[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16F2N2·H2O

  • Mr = 316.34

  • Triclinic, [P \overline 1]

  • a = 7.9424 (9) Å

  • b = 14.5238 (16) Å

  • c = 14.6561 (16) Å

  • α = 75.087 (2)°

  • β = 89.990 (2)°

  • γ = 86.012 (2)°

  • V = 1629.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 294 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 18763 measured reflections

  • 7545 independent reflections

  • 5782 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.140

  • S = 1.00

  • 7545 reflections

  • 433 parameters

  • 13 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1WA⋯N5i 0.82 (3) 2.17 (3) 2.987 (2) 177 (2)
O1W—H1WB⋯O1Wii 0.72 (2) 2.42 (2) 2.894 (3) 125 (2)
O2W—H2WA⋯N3 0.84 (3) 2.16 (3) 2.995 (2) 174 (2)
O2W—H2WB⋯O2Wiii 0.73 (2) 2.42 (2) 2.910 (2) 126 (2)
C17—H17⋯F3iv 0.93 2.46 3.253 (2) 143
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Imidazole derivatives have a wide range of biological properties, such as antifungal (Hori et al., 2000; Mamolo et al., 2004) and antibacterial (Khabnadideh et al., 2003) activities. They are well known analgesic (Ucucu et al., 2001), anti-inflammatory (Noilada et al., 2004), anthelmintic (Dutta et al., 2009), antiparasitic (Quattara et al., 1987), as well as antimicrobial (Sengupta & Bhattacharya, 1983) agents. In view of the interesting biological and pharmacological activities of Imidazole derivatives, the title compound was synthesized and its crystal structure is reported on herein.

The asymmetric unit of the title compound, Fig. 1, consists of two independent molecules (A and B) and two water molecules. In molecule A, the imidazole ring makes dihedral angles of 47.46 (7)° and 60.98 (6)° with the 2,4-difluorophenyl (C15-C20) and the methylphenyl rings (C8-C13), respectively, whereas in molecule B, the corresponding angles are 45.85 (7)° (C33-C38) and 62.78 (7)° (C26-C31). The dihedral angle between the two benzene rings is 65.52 (7)° in molecule A and 64.98 (6)° in molecule B.

In the crystal, the two independent molecules are linked by O—H···N and O—H···O hydrogen bonds forming chains propagating along [100]. These chains are linked via C—H···F hydrogen bonds forming slab-like two-dimensional networks lying parallel to the ab plane (Table 1 and Fig. 2).

Related literature top

For background and the biological properties of imidazole derivatives, see: Dutta et al. (2009); Hori et al. (2000); Khabnadideh et al. (2003); Mamolo et al. (2004); Quattara et al. (1987); Sengupta & Bhattacharya (1983); Ucucu et al. (2001); Noilada et al. (2004). For related structures, see: Rizwana et al. (2013); Gayathri et al. (2010); Rosepriya et al. (2011).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), p-toluidine (1.6 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 2,4-difluorobenzaldehyde (1.1 g, 15 mmol) were added over about 60 min while maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid that separated was purified by column chromatography using hexane:ethyl acetate (1:1 / v:v) as the eluent [Yield: 1.93 g (46%)]. Slow evaporation of a solution of the title compound in chloroform yielded prism-like colourless crystals suitable for X-ray diffraction analysis.

Refinement top

The water H atoms were located in difference Fourier maps and refined with distance restraints: O-H = 0.82 (2) Å and H···H = 1.35 (2) Å, with Uiso(H) = 1.5Ueq(O). The C bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms: C—H = 0.93 - 0.96 Å with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of title compound viewed along the axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).
2-(2,4-Difluorophenyl)-4,5-dimethyl-1-(4-methylphenyl)-1H-imidazole monohydrate top
Crystal data top
C18H16F2N2·H2OZ = 4
Mr = 316.34F(000) = 664
Triclinic, P1Dx = 1.290 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9424 (9) ÅCell parameters from 5735 reflections
b = 14.5238 (16) Åθ = 2–25°
c = 14.6561 (16) ŵ = 0.10 mm1
α = 75.087 (2)°T = 294 K
β = 89.990 (2)°Prism, colourless
γ = 86.012 (2)°0.30 × 0.25 × 0.20 mm
V = 1629.5 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5782 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 28.1°, θmin = 1.8°
ω scanh = 1010
18763 measured reflectionsk = 1818
7545 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0664P)2 + 0.427P]
where P = (Fo2 + 2Fc2)/3
7545 reflections(Δ/σ)max = 0.003
433 parametersΔρmax = 0.26 e Å3
13 restraintsΔρmin = 0.26 e Å3
Crystal data top
C18H16F2N2·H2Oγ = 86.012 (2)°
Mr = 316.34V = 1629.5 (3) Å3
Triclinic, P1Z = 4
a = 7.9424 (9) ÅMo Kα radiation
b = 14.5238 (16) ŵ = 0.10 mm1
c = 14.6561 (16) ÅT = 294 K
α = 75.087 (2)°0.30 × 0.25 × 0.20 mm
β = 89.990 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5782 reflections with I > 2σ(I)
18763 measured reflectionsRint = 0.026
7545 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04813 restraints
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.26 e Å3
7545 reflectionsΔρmin = 0.26 e Å3
433 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 esds 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 > 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
xyzUiso*/Ueq
F10.71950 (16)0.40164 (7)0.19658 (7)0.0736 (4)
F20.85905 (19)0.38610 (9)0.50961 (9)0.0903 (5)
N10.76753 (15)0.21495 (9)0.14701 (8)0.0430 (4)
N30.58511 (15)0.13746 (9)0.24705 (9)0.0466 (4)
C20.69990 (18)0.20050 (10)0.23469 (10)0.0427 (4)
C40.57872 (18)0.10945 (10)0.16402 (11)0.0461 (4)
C50.68894 (18)0.15611 (10)0.10096 (10)0.0445 (4)
C60.7308 (2)0.15112 (14)0.00357 (12)0.0594 (6)
C70.4597 (2)0.03776 (13)0.15297 (14)0.0620 (6)
C80.91789 (17)0.26239 (10)0.11653 (10)0.0418 (4)
C91.06498 (19)0.23288 (11)0.16966 (11)0.0477 (5)
C101.21032 (19)0.27847 (12)0.14079 (12)0.0530 (5)
C111.2127 (2)0.35199 (12)0.06008 (12)0.0524 (5)
C121.0649 (2)0.38001 (12)0.00716 (12)0.0548 (5)
C130.9174 (2)0.33543 (12)0.03523 (11)0.0511 (5)
C141.3728 (3)0.40089 (18)0.03046 (16)0.0807 (8)
C150.74677 (18)0.25045 (10)0.30559 (10)0.0443 (4)
C160.7547 (2)0.34818 (11)0.28531 (11)0.0519 (5)
C170.7926 (3)0.39549 (13)0.35225 (13)0.0620 (6)
C180.8220 (2)0.34102 (14)0.44250 (13)0.0616 (6)
C190.8149 (2)0.24426 (13)0.46788 (12)0.0633 (6)
C200.7775 (2)0.19936 (12)0.39909 (11)0.0539 (5)
F30.2298 (2)0.39845 (7)0.59771 (8)0.0862 (5)
F40.36352 (18)0.38368 (9)0.29162 (8)0.0829 (4)
N40.27463 (15)0.21484 (9)0.74141 (8)0.0440 (4)
N50.09244 (16)0.13610 (9)0.68227 (9)0.0480 (4)
C210.20702 (18)0.19931 (10)0.66138 (10)0.0438 (4)
C220.08604 (19)0.10927 (11)0.77972 (11)0.0472 (4)
C230.19611 (18)0.15691 (11)0.81797 (10)0.0453 (4)
C240.2371 (2)0.15352 (14)0.91762 (11)0.0597 (6)
C250.0326 (2)0.03794 (13)0.82822 (14)0.0631 (6)
C260.42484 (18)0.26301 (10)0.74711 (10)0.0436 (4)
C270.4225 (2)0.33889 (12)0.78742 (12)0.0513 (5)
C280.5694 (2)0.38378 (12)0.79244 (12)0.0563 (5)
C290.7196 (2)0.35333 (13)0.75702 (11)0.0539 (5)
C300.7183 (2)0.27746 (13)0.71679 (12)0.0567 (5)
C310.5731 (2)0.23190 (11)0.71129 (11)0.0510 (5)
C320.8800 (2)0.40155 (17)0.76255 (16)0.0783 (8)
C330.25271 (19)0.24827 (10)0.56501 (10)0.0452 (4)
C340.2631 (2)0.34591 (12)0.53533 (11)0.0556 (5)
C350.3013 (3)0.39309 (12)0.44469 (12)0.0640 (6)
C360.3268 (2)0.33864 (13)0.38162 (12)0.0587 (5)
C370.3160 (2)0.24260 (13)0.40541 (12)0.0604 (6)
C380.2789 (2)0.19759 (12)0.49714 (11)0.0527 (5)
O1W0.9309 (2)0.00201 (13)0.59088 (13)0.0898 (7)
O2W0.4297 (2)0.00074 (12)0.40813 (12)0.0872 (6)
H6A0.685400.095800.008600.0890*
H6B0.851200.146800.002800.0890*
H6C0.682900.207500.040800.0890*
H7A0.345800.065400.150200.0930*
H7B0.473000.017300.205900.0930*
H7C0.483600.019100.095800.0930*
H91.066100.183000.224200.0570*
H101.308900.258900.176800.0640*
H121.064400.429300.047900.0660*
H130.818700.354900.000800.0610*
H14A1.461000.354300.024300.1210*
H14B1.405600.432100.077300.1210*
H14C1.353800.447300.029000.1210*
H170.797900.461500.336700.0740*
H190.834900.209400.530100.0760*
H200.772700.133400.415400.0650*
H24A0.193300.098000.958600.0900*
H24B0.187100.209800.932600.0900*
H24C0.357400.150500.926200.0900*
H25A0.010500.021500.895100.0950*
H25B0.017000.018400.805400.0950*
H25C0.146700.064800.815400.0950*
H270.322700.360000.811200.0620*
H280.567400.434900.819800.0680*
H300.817800.256400.692700.0680*
H310.575000.180800.683800.0610*
H32A0.855300.457100.785600.1170*
H32B0.927500.420300.700800.1170*
H32C0.959300.358000.804700.1170*
H350.309500.458900.427000.0770*
H370.333400.207800.360600.0720*
H380.271100.131800.514000.0630*
H1WA0.974 (4)0.0404 (19)0.614 (2)0.1350*
H1WB0.9002 (18)0.012 (2)0.5427 (11)0.1350*
H2WA0.471 (4)0.0423 (18)0.3654 (17)0.1310*
H2WB0.4005 (19)0.012 (2)0.4516 (11)0.1310*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1162 (9)0.0530 (6)0.0492 (6)0.0004 (6)0.0032 (6)0.0104 (4)
F20.1257 (11)0.0887 (8)0.0712 (7)0.0075 (7)0.0156 (7)0.0475 (7)
N10.0397 (6)0.0493 (7)0.0430 (6)0.0093 (5)0.0014 (5)0.0155 (5)
N30.0430 (6)0.0493 (7)0.0487 (7)0.0082 (5)0.0039 (5)0.0138 (5)
C20.0404 (7)0.0456 (7)0.0429 (7)0.0048 (6)0.0016 (6)0.0127 (6)
C40.0415 (7)0.0480 (8)0.0512 (8)0.0057 (6)0.0010 (6)0.0167 (6)
C50.0402 (7)0.0483 (8)0.0482 (8)0.0058 (6)0.0019 (6)0.0178 (6)
C60.0597 (10)0.0740 (11)0.0536 (9)0.0172 (8)0.0050 (7)0.0296 (8)
C70.0578 (10)0.0644 (10)0.0700 (11)0.0231 (8)0.0033 (8)0.0236 (9)
C80.0384 (7)0.0455 (7)0.0449 (7)0.0083 (6)0.0039 (6)0.0167 (6)
C90.0456 (8)0.0493 (8)0.0486 (8)0.0042 (6)0.0018 (6)0.0129 (6)
C100.0393 (8)0.0667 (10)0.0581 (9)0.0061 (7)0.0033 (6)0.0246 (8)
C110.0478 (8)0.0619 (9)0.0562 (9)0.0184 (7)0.0099 (7)0.0274 (8)
C120.0591 (10)0.0555 (9)0.0494 (8)0.0146 (7)0.0057 (7)0.0099 (7)
C130.0451 (8)0.0572 (9)0.0494 (8)0.0066 (7)0.0027 (6)0.0099 (7)
C140.0623 (11)0.1094 (17)0.0801 (13)0.0417 (11)0.0171 (10)0.0329 (12)
C150.0424 (7)0.0488 (8)0.0444 (7)0.0048 (6)0.0027 (6)0.0165 (6)
C160.0622 (10)0.0497 (8)0.0444 (8)0.0031 (7)0.0029 (7)0.0133 (7)
C170.0801 (12)0.0506 (9)0.0606 (10)0.0072 (8)0.0034 (9)0.0235 (8)
C180.0678 (11)0.0704 (11)0.0566 (10)0.0033 (8)0.0039 (8)0.0348 (9)
C190.0781 (12)0.0663 (11)0.0454 (9)0.0036 (9)0.0087 (8)0.0168 (8)
C200.0630 (10)0.0507 (8)0.0480 (8)0.0011 (7)0.0011 (7)0.0135 (7)
F30.1543 (12)0.0521 (6)0.0568 (6)0.0050 (6)0.0037 (7)0.0254 (5)
F40.1083 (9)0.0851 (8)0.0496 (6)0.0118 (7)0.0139 (6)0.0059 (5)
N40.0427 (6)0.0486 (7)0.0430 (6)0.0066 (5)0.0031 (5)0.0149 (5)
N50.0468 (7)0.0501 (7)0.0503 (7)0.0052 (5)0.0013 (5)0.0181 (6)
C210.0440 (7)0.0448 (7)0.0449 (7)0.0011 (6)0.0014 (6)0.0164 (6)
C220.0424 (7)0.0486 (8)0.0512 (8)0.0038 (6)0.0041 (6)0.0136 (6)
C230.0412 (7)0.0496 (8)0.0453 (7)0.0040 (6)0.0047 (6)0.0125 (6)
C240.0602 (10)0.0737 (11)0.0455 (8)0.0151 (8)0.0042 (7)0.0134 (8)
C250.0589 (10)0.0648 (11)0.0675 (11)0.0197 (8)0.0078 (8)0.0164 (9)
C260.0408 (7)0.0478 (7)0.0419 (7)0.0058 (6)0.0016 (6)0.0103 (6)
C270.0447 (8)0.0591 (9)0.0556 (9)0.0072 (7)0.0071 (7)0.0237 (7)
C280.0571 (9)0.0599 (9)0.0569 (9)0.0135 (7)0.0013 (7)0.0216 (8)
C290.0450 (8)0.0660 (10)0.0463 (8)0.0119 (7)0.0028 (6)0.0045 (7)
C300.0404 (8)0.0686 (10)0.0569 (9)0.0010 (7)0.0054 (7)0.0100 (8)
C310.0491 (8)0.0525 (8)0.0517 (8)0.0002 (7)0.0050 (7)0.0148 (7)
C320.0528 (10)0.1039 (16)0.0762 (13)0.0268 (10)0.0046 (9)0.0139 (11)
C330.0451 (8)0.0476 (8)0.0441 (7)0.0022 (6)0.0002 (6)0.0144 (6)
C340.0728 (11)0.0499 (8)0.0474 (8)0.0005 (7)0.0043 (7)0.0196 (7)
C350.0867 (13)0.0491 (9)0.0543 (10)0.0092 (8)0.0042 (9)0.0090 (7)
C360.0619 (10)0.0673 (10)0.0435 (8)0.0055 (8)0.0041 (7)0.0081 (7)
C370.0719 (11)0.0641 (10)0.0487 (9)0.0036 (8)0.0065 (8)0.0232 (8)
C380.0609 (9)0.0492 (8)0.0504 (8)0.0018 (7)0.0034 (7)0.0179 (7)
O1W0.0968 (12)0.0877 (11)0.0974 (12)0.0125 (9)0.0135 (9)0.0449 (10)
O2W0.0945 (11)0.0827 (10)0.0774 (10)0.0101 (8)0.0206 (8)0.0070 (8)
Geometric parameters (Å, º) top
F1—C161.3500 (19)C10—H100.9300
F2—C181.357 (2)C12—H120.9300
F3—C341.349 (2)C13—H130.9300
F4—C361.355 (2)C14—H14C0.9600
O1W—H1WB0.722 (16)C14—H14A0.9600
O1W—H1WA0.82 (3)C14—H14B0.9600
O2W—H2WB0.73 (2)C17—H170.9300
O2W—H2WA0.84 (3)C19—H190.9300
N1—C51.3952 (19)C20—H200.9300
N1—C81.4340 (18)C21—C331.467 (2)
N1—C21.3640 (18)C22—C231.357 (2)
N3—C21.3164 (19)C22—C251.491 (2)
N3—C41.381 (2)C23—C241.484 (2)
N4—C231.3938 (19)C26—C271.377 (2)
N4—C261.4374 (19)C26—C311.384 (2)
N4—C211.3668 (19)C27—C281.387 (2)
N5—C211.318 (2)C28—C291.390 (2)
N5—C221.382 (2)C29—C321.508 (3)
C2—C151.473 (2)C29—C301.378 (3)
C4—C51.356 (2)C30—C311.381 (2)
C4—C71.493 (2)C33—C341.381 (2)
C5—C61.484 (2)C33—C381.389 (2)
C8—C131.376 (2)C34—C351.374 (2)
C8—C91.383 (2)C35—C361.369 (3)
C9—C101.383 (2)C36—C371.357 (3)
C10—C111.376 (2)C37—C381.377 (2)
C11—C141.509 (3)C24—H24A0.9600
C11—C121.384 (2)C24—H24B0.9600
C12—C131.389 (2)C24—H24C0.9600
C15—C161.379 (2)C25—H25C0.9600
C15—C201.393 (2)C25—H25A0.9600
C16—C171.379 (3)C25—H25B0.9600
C17—C181.366 (3)C27—H270.9300
C18—C191.363 (3)C28—H280.9300
C19—C201.377 (2)C30—H300.9300
C6—H6C0.9600C31—H310.9300
C6—H6B0.9600C32—H32A0.9600
C6—H6A0.9600C32—H32B0.9600
C7—H7C0.9600C32—H32C0.9600
C7—H7A0.9600C35—H350.9300
C7—H7B0.9600C37—H370.9300
C9—H90.9300C38—H380.9300
H1WA—O1W—H1WB125 (3)C16—C17—H17122.00
H2WA—O2W—H2WB121 (3)C18—C19—H19121.00
C5—N1—C8125.27 (12)C20—C19—H19121.00
C2—N1—C5107.05 (12)C19—C20—H20119.00
C2—N1—C8126.05 (12)C15—C20—H20119.00
C2—N3—C4105.81 (12)N5—C21—C33124.47 (13)
C23—N4—C26125.20 (12)N4—C21—C33124.54 (13)
C21—N4—C23107.14 (12)N4—C21—N5110.98 (13)
C21—N4—C26126.10 (12)C23—C22—C25129.00 (15)
C21—N5—C22105.96 (13)N5—C22—C25120.43 (14)
N3—C2—C15124.42 (13)N5—C22—C23110.56 (13)
N1—C2—N3111.20 (13)N4—C23—C22105.36 (13)
N1—C2—C15124.37 (13)N4—C23—C24123.10 (14)
N3—C4—C7120.38 (14)C22—C23—C24131.53 (14)
N3—C4—C5110.69 (13)N4—C26—C27120.98 (13)
C5—C4—C7128.92 (15)C27—C26—C31120.14 (14)
C4—C5—C6131.75 (14)N4—C26—C31118.88 (13)
N1—C5—C4105.25 (12)C26—C27—C28119.81 (15)
N1—C5—C6123.00 (13)C27—C28—C29120.84 (16)
N1—C8—C9118.94 (13)C30—C29—C32120.69 (16)
N1—C8—C13120.88 (13)C28—C29—C30118.17 (15)
C9—C8—C13120.18 (14)C28—C29—C32121.14 (17)
C8—C9—C10119.23 (15)C29—C30—C31121.73 (15)
C9—C10—C11121.64 (15)C26—C31—C30119.32 (15)
C12—C11—C14121.01 (17)C21—C33—C38120.50 (14)
C10—C11—C12118.42 (15)C34—C33—C38116.59 (14)
C10—C11—C14120.57 (16)C21—C33—C34122.82 (14)
C11—C12—C13120.81 (16)C33—C34—C35123.51 (16)
C8—C13—C12119.72 (15)F3—C34—C33118.53 (14)
C2—C15—C16123.06 (13)F3—C34—C35117.94 (16)
C16—C15—C20116.83 (14)C34—C35—C36116.79 (17)
C2—C15—C20120.04 (14)F4—C36—C37119.22 (16)
C15—C16—C17123.20 (15)C35—C36—C37122.91 (16)
F1—C16—C17117.44 (15)F4—C36—C35117.87 (17)
F1—C16—C15119.34 (14)C36—C37—C38118.70 (17)
C16—C17—C18116.94 (18)C33—C38—C37121.48 (16)
F2—C18—C19118.95 (16)C23—C24—H24A110.00
F2—C18—C17117.96 (18)H24A—C24—H24B109.00
C17—C18—C19123.10 (18)H24A—C24—H24C109.00
C18—C19—C20118.38 (16)H24B—C24—H24C110.00
C15—C20—C19121.56 (16)C23—C24—H24B109.00
C5—C6—H6A109.00C23—C24—H24C109.00
H6B—C6—H6C110.00C22—C25—H25A109.00
C5—C6—H6C109.00H25A—C25—H25B110.00
H6A—C6—H6B109.00C22—C25—H25B109.00
C5—C6—H6B109.00C22—C25—H25C109.00
H6A—C6—H6C109.00H25B—C25—H25C109.00
C4—C7—H7C110.00H25A—C25—H25C109.00
H7A—C7—H7B109.00C28—C27—H27120.00
C4—C7—H7B109.00C26—C27—H27120.00
C4—C7—H7A109.00C27—C28—H28120.00
H7A—C7—H7C110.00C29—C28—H28120.00
H7B—C7—H7C109.00C29—C30—H30119.00
C8—C9—H9120.00C31—C30—H30119.00
C10—C9—H9120.00C26—C31—H31120.00
C11—C10—H10119.00C30—C31—H31120.00
C9—C10—H10119.00C29—C32—H32B109.00
C11—C12—H12120.00C29—C32—H32A109.00
C13—C12—H12120.00H32A—C32—H32C110.00
C8—C13—H13120.00C29—C32—H32C109.00
C12—C13—H13120.00H32A—C32—H32B109.00
H14A—C14—H14B109.00H32B—C32—H32C109.00
H14A—C14—H14C109.00C36—C35—H35122.00
C11—C14—H14A109.00C34—C35—H35122.00
C11—C14—H14B109.00C36—C37—H37121.00
C11—C14—H14C109.00C38—C37—H37121.00
H14B—C14—H14C109.00C37—C38—H38119.00
C18—C17—H17121.00C33—C38—H38119.00
C5—N1—C2—N30.12 (17)C14—C11—C12—C13179.34 (18)
C5—N1—C2—C15178.94 (14)C10—C11—C12—C130.5 (3)
C8—N1—C2—N3166.06 (13)C11—C12—C13—C80.1 (3)
C8—N1—C2—C1515.1 (2)C2—C15—C16—C17177.59 (17)
C2—N1—C5—C40.17 (16)C20—C15—C16—F1177.42 (14)
C2—N1—C5—C6179.31 (14)C2—C15—C16—F10.5 (2)
C8—N1—C5—C4165.92 (13)C2—C15—C20—C19177.35 (14)
C8—N1—C5—C613.2 (2)C16—C15—C20—C190.3 (2)
C2—N1—C8—C952.4 (2)C20—C15—C16—C170.7 (2)
C2—N1—C8—C13128.40 (17)C15—C16—C17—C180.4 (3)
C5—N1—C8—C9111.13 (17)F1—C16—C17—C18177.69 (17)
C5—N1—C8—C1368.1 (2)C16—C17—C18—F2179.81 (17)
C4—N3—C2—N10.34 (17)C16—C17—C18—C190.2 (3)
C4—N3—C2—C15179.16 (14)C17—C18—C19—C200.5 (3)
C2—N3—C4—C50.45 (17)F2—C18—C19—C20179.88 (15)
C2—N3—C4—C7179.74 (14)C18—C19—C20—C150.2 (2)
C23—N4—C21—N50.03 (17)N4—C21—C33—C3447.0 (2)
C23—N4—C21—C33178.51 (14)N4—C21—C33—C38136.58 (16)
C26—N4—C21—N5166.26 (14)N5—C21—C33—C34131.35 (17)
C26—N4—C21—C3315.2 (2)N5—C21—C33—C3845.1 (2)
C21—N4—C23—C220.31 (17)N5—C22—C23—N40.49 (18)
C21—N4—C23—C24179.64 (15)N5—C22—C23—C24179.73 (16)
C26—N4—C23—C22166.13 (14)C25—C22—C23—N4179.64 (16)
C26—N4—C23—C2413.2 (2)C25—C22—C23—C241.1 (3)
C21—N4—C26—C27126.12 (17)N4—C26—C27—C28179.68 (14)
C21—N4—C26—C3153.9 (2)C31—C26—C27—C280.3 (2)
C23—N4—C26—C2770.0 (2)N4—C26—C31—C30179.73 (14)
C23—N4—C26—C31110.01 (17)C27—C26—C31—C300.3 (2)
C22—N5—C21—N40.27 (17)C26—C27—C28—C290.2 (2)
C22—N5—C21—C33178.81 (14)C27—C28—C29—C300.1 (3)
C21—N5—C22—C230.48 (18)C27—C28—C29—C32179.77 (17)
C21—N5—C22—C25179.72 (15)C28—C29—C30—C310.1 (3)
N1—C2—C15—C1648.6 (2)C32—C29—C30—C31179.72 (17)
N1—C2—C15—C20134.62 (16)C29—C30—C31—C260.1 (3)
N3—C2—C15—C16130.11 (17)C21—C33—C34—F30.0 (2)
N3—C2—C15—C2046.7 (2)C21—C33—C34—C35178.20 (17)
N3—C4—C5—N10.38 (17)C38—C33—C34—F3176.57 (15)
N3—C4—C5—C6179.41 (16)C38—C33—C34—C351.6 (3)
C7—C4—C5—N1179.59 (15)C21—C33—C38—C37177.67 (15)
C7—C4—C5—C61.4 (3)C34—C33—C38—C371.0 (2)
N1—C8—C9—C10179.85 (14)F3—C34—C35—C36177.02 (17)
C13—C8—C9—C100.9 (2)C33—C34—C35—C361.2 (3)
N1—C8—C13—C12179.83 (15)C34—C35—C36—F4179.56 (17)
C9—C8—C13—C120.6 (2)C34—C35—C36—C370.1 (3)
C8—C9—C10—C110.5 (3)F4—C36—C37—C38179.88 (15)
C9—C10—C11—C120.1 (3)C35—C36—C37—C380.5 (3)
C9—C10—C11—C14179.66 (18)C36—C37—C38—C330.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···N5i0.82 (3)2.17 (3)2.987 (2)177 (2)
O1W—H1WB···O1Wii0.72 (2)2.42 (2)2.894 (3)125 (2)
O2W—H2WA···N30.84 (3)2.16 (3)2.995 (2)174 (2)
O2W—H2WB···O2Wiii0.73 (2)2.42 (2)2.910 (2)126 (2)
C17—H17···F3iv0.932.463.253 (2)143
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z+1; (iii) x+1, y, z+1; (iv) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···N5i0.82 (3)2.17 (3)2.987 (2)177 (2)
O1W—H1WB···O1Wii0.722 (16)2.417 (17)2.894 (3)125.2 (16)
O2W—H2WA···N30.84 (3)2.16 (3)2.995 (2)174 (2)
O2W—H2WB···O2Wiii0.73 (2)2.419 (16)2.910 (2)126.1 (16)
C17—H17···F3iv0.932.463.253 (2)143
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z+1; (iii) x+1, y, z+1; (iv) x+1, y+1, z+1.
 

Acknowledgements

SR thanks the University Grants Commission for financial support of this work (grant MRP-4335/12).

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDutta, S., Mariappan, G., Roy, S. & Verma, M. (2009). Indian Drugs, 46, 50–53.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationGayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.  Web of Science CSD CrossRef IUCr Journals
First citationHori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60–64.  CrossRef PubMed CAS
First citationKhabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863–2865.  Web of Science CrossRef PubMed CAS
First citationMamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). ARKIVOC, v, 231–250.  CrossRef
First citationNoilada, A., Koyunoglu, S., Saygili, N., Kupeli, E., Noilada, E., Bedir, E. & Khan, I. (2004). Arch. Pharm. Pharm. Med. Chem. 337, 96–104.
First citationQuattara, L., Debaert, M. & Cavier, R. (1987). Il Farmaco, 42, 449–456.  CAS
First citationRizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.  CSD CrossRef IUCr Journals
First citationRosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.  Web of Science CSD CrossRef IUCr Journals
First citationSengupta, A. K. & Bhattacharya, T. (1983). J. Indian Chem. Soc. 60, 373–376.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationUcucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285–290.  PubMed CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 11| November 2013| Pages o1599-o1600
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds