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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1036

1,1′-Bis(4-fluoro­phen­yl)-3,3′-diiso­butyl-4,4′-diphen­­oxy-1H,1′H-4,4′-bi­pyrazole-5,5′(4H,4′H)-dione

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
*Correspondence e-mail: hkfun@usm.my

(Received 15 March 2011; accepted 29 March 2011; online 7 April 2011)

In the title compound, C38H36F2N4O4, the pyrazole rings form dihedral angles of 50.02 (4) and 18.05 (4)° with their attached fluorobenzene rings, and make dihedral angles of 76.08 (4) and 73.54 (5)° with the aromatic ring of the attached phen­oxy group. In the crystal, the molecules are connected by weak C—H⋯π inter­actions.

Related literature

For the synthesis and applications of pyrazole derivatives, see: Venkat Ragavan et al. (2009[Venkat Ragavan, R., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur.J. Med. Chem. 44, 3852-3857.], 2010[Venkat Ragavan, R., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur.J. Med. Chem. 45, 1173-1180.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C38H36F2N4O4

  • Mr = 650.71

  • Monoclinic, P 21

  • a = 11.3875 (5) Å

  • b = 11.4582 (5) Å

  • c = 13.4885 (6) Å

  • β = 109.752 (1)°

  • V = 1656.43 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.53 × 0.21 × 0.14 mm

Data collection
  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.987

  • 26247 measured reflections

  • 6956 independent reflections

  • 6490 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.03

  • 6956 reflections

  • 437 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2=C8 double bond. Cg3 and Cg5 are the centroids of the C1–C6 and C19–C24 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15ACg5i 0.93 2.82 3.6941 (14) 157
C20—H20ACg1 0.93 2.54 2.9632 (12) 135
C29—H29ACg3ii 0.93 2.82 3.4701 (15) 128
C36—H36ACg3i 0.98 2.91 3.7529 (15) 145
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z]; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strains has led to the development of new antimicrobial compounds. In particular pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazole is an important class of heterocyclic compound and many pyrazole derivatives are reported to have the broad spectrum of biological activities, such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling, and antiviral activities. Pyrazole derivatives also act as antiangiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists, kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new antimicrobial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Venkat Ragavan et al., 2009, 2010).

In the molecule of the title compound (Fig. 1), the pyrazole rings (N1–N2/C7–C9; N3–N4/C10–C12) form dihedral angles of 50.02 (4) and 18.05 (4)° with the attached benzene rings (C1–C6; C13–C18), and of 76.08 (4) and 73.54 (5)° with the aromatic ring of the attached phenoxy group (C19–C24; C25–C30). In the crystal structure (Fig. 2), there is no classical hydrogen bond and stabilization is provided by weak C—H···π interactions (Table 1), involving the centroids of the N2C8 double bond (centroid Cg1), C1–C6 ring (centroid Cg3) and C19–C24 ring (centroid Cg5).

Related literature top

For the synthesis and applications of pyrazole derivatives, see: Venkat Ragavan et al. (2009, 2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

1-(4-Fluorophenyl)-3-isobutyl-4-phenoxy-1H-pyrazole- 5(4H)-one was synthesized using the method reported in the literature (Venkat Ragavan et al., 2010) and was converted into the title compound under the experimental condition. Single crystals of the title compound were obtained byu slow evaporation of an ethanol / chloroform (1:1 v/v) solution. Yield: 52%. M. p. 198 °C.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93–0.97 Å and with with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating group model was applied to the methyl groups. 4666 Friedel pairs were merged in the final refinement cycles.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a axis. Hydrogen atoms are omitted for clairty.
1,1'-Bis(4-fluorophenyl)-3,3'-diisobutyl-4,4'-diphenoxy-1H,1'H-4,4'-bipyrazole-5,5'(4H,4'H)-dione top
Crystal data top
C38H36F2N4O4F(000) = 684
Mr = 650.71Dx = 1.305 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9923 reflections
a = 11.3875 (5) Åθ = 2.6–33.9°
b = 11.4582 (5) ŵ = 0.09 mm1
c = 13.4885 (6) ÅT = 100 K
β = 109.752 (1)°Block, colourless
V = 1656.43 (13) Å30.53 × 0.21 × 0.14 mm
Z = 2
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
6956 independent reflections
Radiation source: fine-focus sealed tube6490 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 34.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1717
Tmin = 0.953, Tmax = 0.987k = 1617
26247 measured reflectionsl = 2121
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0646P)2 + 0.0777P]
where P = (Fo2 + 2Fc2)/3
6956 reflections(Δ/σ)max < 0.001
437 parametersΔρmax = 0.38 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C38H36F2N4O4V = 1656.43 (13) Å3
Mr = 650.71Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.3875 (5) ŵ = 0.09 mm1
b = 11.4582 (5) ÅT = 100 K
c = 13.4885 (6) Å0.53 × 0.21 × 0.14 mm
β = 109.752 (1)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
6956 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6490 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.987Rint = 0.033
26247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.097H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
6956 reflectionsΔρmin = 0.19 e Å3
437 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.16157 (12)0.88614 (12)0.18115 (9)0.0445 (3)
F20.06578 (9)0.23698 (10)0.42001 (6)0.02846 (19)
O10.13281 (8)0.47312 (9)0.13477 (8)0.01997 (17)
O20.43391 (8)0.32469 (9)0.06204 (7)0.01912 (17)
O30.31599 (9)0.37927 (8)0.33952 (7)0.01736 (16)
O40.43323 (8)0.21142 (8)0.26514 (7)0.01669 (15)
N10.31858 (9)0.55722 (10)0.13450 (8)0.01593 (17)
N20.44800 (9)0.54499 (10)0.19062 (8)0.01617 (17)
N30.15255 (9)0.20611 (10)0.06656 (8)0.01630 (17)
N40.23161 (9)0.25123 (10)0.01456 (7)0.01599 (17)
C10.33645 (12)0.64873 (14)0.02151 (10)0.0223 (2)
H1A0.40090.59760.01880.027*
C20.29730 (14)0.73220 (16)0.10091 (11)0.0280 (3)
H2A0.33570.73840.15160.034*
C30.20009 (14)0.80572 (14)0.10295 (11)0.0273 (3)
C40.14072 (13)0.80168 (13)0.02921 (11)0.0250 (2)
H4A0.07600.85270.03270.030*
C50.18107 (12)0.71836 (12)0.05087 (10)0.0198 (2)
H5A0.14330.71350.10200.024*
C60.27778 (10)0.64274 (11)0.05391 (9)0.01593 (19)
C70.24579 (10)0.47989 (10)0.16516 (9)0.01526 (18)
C80.46309 (10)0.45898 (10)0.25547 (9)0.01485 (18)
C90.34030 (10)0.39846 (10)0.24473 (8)0.01406 (18)
C100.33402 (10)0.27539 (10)0.19366 (8)0.01360 (17)
C110.20658 (10)0.21832 (10)0.16633 (9)0.01466 (18)
C120.34409 (10)0.28881 (11)0.08242 (8)0.01450 (18)
C130.19215 (11)0.24391 (11)0.09684 (9)0.01556 (19)
C140.09432 (11)0.16901 (12)0.15010 (9)0.0179 (2)
H14A0.05810.12150.11250.022*
C150.05129 (12)0.16586 (13)0.25994 (9)0.0208 (2)
H15A0.01430.11710.29670.025*
C160.10863 (12)0.23713 (13)0.31272 (9)0.0205 (2)
C170.20826 (12)0.30842 (13)0.26164 (9)0.0212 (2)
H17A0.24670.35280.29970.025*
C180.25023 (12)0.31284 (13)0.15225 (9)0.0198 (2)
H18A0.31640.36130.11620.024*
C190.28076 (11)0.47180 (11)0.38968 (9)0.01629 (19)
C200.31030 (12)0.58837 (11)0.38105 (10)0.0196 (2)
H20A0.35300.61000.33610.024*
C210.27516 (13)0.67257 (12)0.44059 (11)0.0234 (2)
H21A0.29470.75060.43530.028*
C220.21111 (13)0.64049 (14)0.50775 (10)0.0250 (3)
H22A0.18900.69650.54810.030*
C230.18034 (13)0.52373 (14)0.51408 (10)0.0238 (2)
H23A0.13630.50240.55810.029*
C240.21458 (12)0.43851 (12)0.45541 (9)0.0200 (2)
H24A0.19370.36070.45990.024*
C250.44075 (10)0.09116 (10)0.25076 (9)0.01556 (19)
C260.47531 (12)0.02552 (12)0.34262 (10)0.0199 (2)
H26A0.48750.06130.40720.024*
C270.49152 (14)0.09463 (13)0.33716 (11)0.0251 (3)
H27A0.51490.13900.39850.030*
C280.47307 (13)0.14878 (12)0.24071 (12)0.0255 (3)
H28A0.48310.22910.23730.031*
C290.43958 (13)0.08168 (12)0.14961 (11)0.0242 (2)
H29A0.42770.11750.08510.029*
C300.42349 (13)0.03901 (12)0.15369 (10)0.0208 (2)
H30A0.40160.08370.09260.025*
C310.58776 (11)0.42088 (11)0.32904 (9)0.0178 (2)
H31A0.61640.35610.29700.021*
H31B0.57720.39220.39310.021*
C320.69001 (11)0.51488 (12)0.35900 (9)0.0180 (2)
H32A0.69270.55220.29440.022*
C330.66345 (14)0.60810 (14)0.42947 (12)0.0270 (3)
H33A0.72720.66690.44510.040*
H33B0.66270.57290.49380.040*
H33C0.58370.64310.39380.040*
C340.81648 (12)0.45735 (14)0.41513 (11)0.0240 (2)
H34A0.88080.51560.43220.036*
H34B0.83290.39980.36970.036*
H34C0.81500.42050.47860.036*
C350.14649 (11)0.18458 (11)0.24507 (9)0.0181 (2)
H35A0.10610.25310.26110.022*
H35B0.21150.16110.30950.022*
C360.04988 (12)0.08607 (12)0.21154 (10)0.0205 (2)
H36A0.00920.10410.14140.025*
C370.11105 (18)0.03154 (15)0.20684 (16)0.0352 (3)
H37A0.15480.02710.15730.053*
H37B0.04800.09090.18500.053*
H37C0.16880.05050.27530.053*
C380.02151 (14)0.08170 (16)0.28949 (12)0.0294 (3)
H38A0.08410.02190.26840.044*
H38B0.06060.15580.29020.044*
H38C0.03550.06470.35870.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0486 (6)0.0413 (6)0.0364 (5)0.0022 (5)0.0051 (4)0.0265 (5)
F20.0307 (4)0.0377 (5)0.0146 (3)0.0004 (4)0.0046 (3)0.0004 (3)
O10.0144 (3)0.0176 (4)0.0279 (4)0.0001 (3)0.0071 (3)0.0017 (4)
O20.0164 (3)0.0223 (4)0.0205 (4)0.0038 (3)0.0086 (3)0.0024 (3)
O30.0251 (4)0.0127 (3)0.0172 (3)0.0003 (3)0.0110 (3)0.0009 (3)
O40.0173 (3)0.0116 (3)0.0177 (3)0.0008 (3)0.0014 (3)0.0015 (3)
N10.0134 (4)0.0147 (4)0.0191 (4)0.0004 (3)0.0047 (3)0.0042 (3)
N20.0131 (4)0.0161 (4)0.0180 (4)0.0004 (3)0.0035 (3)0.0008 (4)
N30.0153 (4)0.0175 (4)0.0171 (4)0.0022 (4)0.0069 (3)0.0015 (4)
N40.0143 (4)0.0196 (4)0.0139 (3)0.0036 (4)0.0046 (3)0.0001 (3)
C10.0208 (5)0.0258 (6)0.0217 (5)0.0003 (5)0.0092 (4)0.0035 (5)
C20.0284 (6)0.0332 (7)0.0229 (5)0.0045 (6)0.0093 (5)0.0075 (6)
C30.0276 (6)0.0250 (6)0.0236 (5)0.0036 (5)0.0011 (5)0.0113 (5)
C40.0217 (5)0.0195 (6)0.0302 (6)0.0019 (5)0.0037 (5)0.0068 (5)
C50.0183 (5)0.0173 (5)0.0229 (5)0.0010 (4)0.0058 (4)0.0026 (4)
C60.0158 (4)0.0143 (4)0.0169 (4)0.0010 (4)0.0045 (3)0.0023 (4)
C70.0156 (4)0.0125 (4)0.0185 (4)0.0004 (4)0.0068 (3)0.0006 (4)
C80.0146 (4)0.0128 (4)0.0166 (4)0.0009 (4)0.0045 (3)0.0016 (4)
C90.0157 (4)0.0120 (4)0.0153 (4)0.0003 (4)0.0063 (3)0.0002 (4)
C100.0135 (4)0.0119 (4)0.0148 (4)0.0009 (3)0.0040 (3)0.0011 (4)
C110.0156 (4)0.0126 (4)0.0163 (4)0.0014 (4)0.0060 (3)0.0004 (4)
C120.0139 (4)0.0146 (4)0.0148 (4)0.0002 (4)0.0046 (3)0.0013 (4)
C130.0158 (4)0.0164 (5)0.0138 (4)0.0001 (4)0.0043 (3)0.0002 (4)
C140.0176 (5)0.0182 (5)0.0174 (4)0.0016 (4)0.0051 (4)0.0008 (4)
C150.0202 (5)0.0221 (6)0.0179 (4)0.0014 (5)0.0035 (4)0.0027 (4)
C160.0208 (5)0.0248 (6)0.0148 (4)0.0040 (5)0.0045 (4)0.0003 (4)
C170.0220 (5)0.0246 (6)0.0174 (4)0.0001 (5)0.0073 (4)0.0031 (5)
C180.0198 (5)0.0221 (5)0.0171 (4)0.0037 (4)0.0055 (4)0.0015 (4)
C190.0183 (4)0.0152 (4)0.0155 (4)0.0018 (4)0.0059 (3)0.0017 (4)
C200.0221 (5)0.0153 (5)0.0225 (5)0.0000 (4)0.0088 (4)0.0030 (4)
C210.0265 (6)0.0176 (5)0.0250 (5)0.0010 (5)0.0075 (4)0.0054 (5)
C220.0291 (6)0.0257 (6)0.0209 (5)0.0082 (5)0.0091 (4)0.0044 (5)
C230.0275 (6)0.0270 (6)0.0201 (5)0.0088 (5)0.0119 (4)0.0032 (5)
C240.0235 (5)0.0200 (5)0.0190 (4)0.0031 (4)0.0101 (4)0.0021 (4)
C250.0135 (4)0.0122 (4)0.0195 (4)0.0007 (4)0.0037 (3)0.0016 (4)
C260.0216 (5)0.0147 (5)0.0210 (5)0.0013 (4)0.0040 (4)0.0000 (4)
C270.0251 (6)0.0160 (5)0.0289 (6)0.0017 (5)0.0022 (5)0.0027 (5)
C280.0227 (6)0.0133 (5)0.0355 (7)0.0020 (4)0.0035 (5)0.0027 (5)
C290.0243 (6)0.0171 (5)0.0282 (6)0.0014 (5)0.0048 (5)0.0078 (5)
C300.0242 (5)0.0158 (5)0.0204 (5)0.0018 (4)0.0052 (4)0.0028 (4)
C310.0168 (5)0.0136 (4)0.0197 (4)0.0012 (4)0.0016 (4)0.0003 (4)
C320.0167 (4)0.0170 (5)0.0183 (4)0.0022 (4)0.0032 (4)0.0001 (4)
C330.0255 (6)0.0211 (6)0.0314 (6)0.0036 (5)0.0059 (5)0.0087 (5)
C340.0171 (5)0.0246 (6)0.0263 (5)0.0011 (5)0.0021 (4)0.0008 (5)
C350.0201 (5)0.0184 (5)0.0178 (4)0.0040 (4)0.0089 (4)0.0000 (4)
C360.0211 (5)0.0201 (5)0.0211 (5)0.0054 (5)0.0080 (4)0.0020 (4)
C370.0394 (8)0.0184 (6)0.0518 (9)0.0061 (6)0.0208 (7)0.0006 (7)
C380.0266 (6)0.0362 (8)0.0286 (6)0.0095 (6)0.0135 (5)0.0045 (6)
Geometric parameters (Å, º) top
F1—C31.3570 (17)C20—C211.3975 (18)
F2—C161.3620 (14)C20—H20A0.9300
O1—C71.2136 (14)C21—C221.391 (2)
O2—C121.2169 (14)C21—H21A0.9300
O3—C191.3880 (15)C22—C231.393 (2)
O3—C91.4138 (13)C22—H22A0.9300
O4—C251.3981 (15)C23—C241.3930 (19)
O4—C101.4166 (14)C23—H23A0.9300
N1—C71.3693 (15)C24—H24A0.9300
N1—N21.4179 (14)C25—C261.3879 (17)
N1—C61.4200 (15)C25—C301.3914 (16)
N2—C81.2901 (15)C26—C271.3943 (19)
N3—C111.2843 (14)C26—H26A0.9300
N3—N41.4131 (13)C27—C281.392 (2)
N4—C121.3680 (15)C27—H27A0.9300
N4—C131.4180 (14)C28—C291.389 (2)
C1—C21.392 (2)C28—H28A0.9300
C1—C61.3949 (17)C29—C301.3985 (19)
C1—H1A0.9300C29—H29A0.9300
C2—C31.384 (2)C30—H30A0.9300
C2—H2A0.9300C31—C321.5367 (17)
C3—C41.380 (2)C31—H31A0.9700
C4—C51.3977 (18)C31—H31B0.9700
C4—H4A0.9300C32—C331.5265 (19)
C5—C61.3910 (17)C32—C341.5313 (18)
C5—H5A0.9300C32—H32A0.9800
C7—C91.5492 (16)C33—H33A0.9600
C8—C311.4961 (16)C33—H33B0.9600
C8—C91.5232 (16)C33—H33C0.9600
C9—C101.5604 (16)C34—H34A0.9600
C10—C111.5192 (16)C34—H34B0.9600
C10—C121.5506 (15)C34—H34C0.9600
C11—C351.4956 (15)C35—C361.5338 (18)
C13—C141.3974 (17)C35—H35A0.9700
C13—C181.3978 (17)C35—H35B0.9700
C14—C151.3949 (16)C36—C371.528 (2)
C14—H14A0.9300C36—C381.5320 (18)
C15—C161.3836 (19)C36—H36A0.9800
C15—H15A0.9300C37—H37A0.9600
C16—C171.3787 (19)C37—H37B0.9600
C17—C181.3898 (16)C37—H37C0.9600
C17—H17A0.9300C38—H38A0.9600
C18—H18A0.9300C38—H38B0.9600
C19—C201.3918 (18)C38—H38C0.9600
C19—C241.3969 (16)
C19—O3—C9119.95 (10)C22—C21—H21A119.8
C25—O4—C10119.19 (9)C20—C21—H21A119.8
C7—N1—N2113.63 (9)C21—C22—C23119.47 (12)
C7—N1—C6127.08 (10)C21—C22—H22A120.3
N2—N1—C6119.28 (9)C23—C22—H22A120.3
C8—N2—N1108.28 (10)C22—C23—C24120.93 (12)
C11—N3—N4108.68 (9)C22—C23—H23A119.5
C12—N4—N3113.12 (9)C24—C23—H23A119.5
C12—N4—C13128.13 (10)C23—C24—C19118.93 (13)
N3—N4—C13118.52 (9)C23—C24—H24A120.5
C2—C1—C6119.15 (13)C19—C24—H24A120.5
C2—C1—H1A120.4C26—C25—C30120.97 (11)
C6—C1—H1A120.4C26—C25—O4114.99 (10)
C3—C2—C1118.66 (12)C30—C25—O4123.91 (11)
C3—C2—H2A120.7C25—C26—C27119.38 (12)
C1—C2—H2A120.7C25—C26—H26A120.3
F1—C3—C4118.35 (15)C27—C26—H26A120.3
F1—C3—C2118.36 (14)C28—C27—C26120.58 (13)
C4—C3—C2123.29 (13)C28—C27—H27A119.7
C3—C4—C5117.83 (13)C26—C27—H27A119.7
C3—C4—H4A121.1C29—C28—C27119.32 (13)
C5—C4—H4A121.1C29—C28—H28A120.3
C6—C5—C4119.90 (12)C27—C28—H28A120.3
C6—C5—H5A120.0C28—C29—C30120.86 (13)
C4—C5—H5A120.0C28—C29—H29A119.6
C5—C6—C1121.16 (11)C30—C29—H29A119.6
C5—C6—N1120.23 (10)C25—C30—C29118.88 (13)
C1—C6—N1118.61 (11)C25—C30—H30A120.6
O1—C7—N1128.33 (11)C29—C30—H30A120.6
O1—C7—C9127.19 (11)C8—C31—C32115.77 (10)
N1—C7—C9104.43 (9)C8—C31—H31A108.3
N2—C8—C31123.48 (11)C32—C31—H31A108.3
N2—C8—C9112.06 (10)C8—C31—H31B108.3
C31—C8—C9124.40 (10)C32—C31—H31B108.3
O3—C9—C8116.03 (9)H31A—C31—H31B107.4
O3—C9—C7114.68 (9)C33—C32—C34110.15 (11)
C8—C9—C7101.08 (9)C33—C32—C31111.23 (10)
O3—C9—C10105.36 (9)C34—C32—C31109.31 (11)
C8—C9—C10110.92 (9)C33—C32—H32A108.7
C7—C9—C10108.72 (9)C34—C32—H32A108.7
O4—C10—C11114.78 (9)C31—C32—H32A108.7
O4—C10—C12114.02 (9)C32—C33—H33A109.5
C11—C10—C12100.65 (9)C32—C33—H33B109.5
O4—C10—C9105.08 (8)H33A—C33—H33B109.5
C11—C10—C9113.18 (9)C32—C33—H33C109.5
C12—C10—C9109.28 (9)H33A—C33—H33C109.5
N3—C11—C35122.94 (10)H33B—C33—H33C109.5
N3—C11—C10112.42 (9)C32—C34—H34A109.5
C35—C11—C10124.59 (10)C32—C34—H34B109.5
O2—C12—N4128.57 (10)H34A—C34—H34B109.5
O2—C12—C10126.50 (10)C32—C34—H34C109.5
N4—C12—C10104.92 (9)H34A—C34—H34C109.5
C14—C13—C18120.75 (10)H34B—C34—H34C109.5
C14—C13—N4119.55 (10)C11—C35—C36115.82 (10)
C18—C13—N4119.70 (10)C11—C35—H35A108.3
C15—C14—C13119.65 (11)C36—C35—H35A108.3
C15—C14—H14A120.2C11—C35—H35B108.3
C13—C14—H14A120.2C36—C35—H35B108.3
C16—C15—C14118.28 (12)H35A—C35—H35B107.4
C16—C15—H15A120.9C37—C36—C38110.78 (13)
C14—C15—H15A120.9C37—C36—C35111.69 (11)
F2—C16—C17118.07 (12)C38—C36—C35108.41 (11)
F2—C16—C15118.95 (12)C37—C36—H36A108.6
C17—C16—C15122.98 (11)C38—C36—H36A108.6
C16—C17—C18118.80 (12)C35—C36—H36A108.6
C16—C17—H17A120.6C36—C37—H37A109.5
C18—C17—H17A120.6C36—C37—H37B109.5
C17—C18—C13119.47 (12)H37A—C37—H37B109.5
C17—C18—H18A120.3C36—C37—H37C109.5
C13—C18—H18A120.3H37A—C37—H37C109.5
O3—C19—C20125.06 (10)H37B—C37—H37C109.5
O3—C19—C24114.06 (11)C36—C38—H38A109.5
C20—C19—C24120.84 (11)C36—C38—H38B109.5
C19—C20—C21119.35 (12)H38A—C38—H38B109.5
C19—C20—H20A120.3C36—C38—H38C109.5
C21—C20—H20A120.3H38A—C38—H38C109.5
C22—C21—C20120.46 (13)H38B—C38—H38C109.5
C7—N1—N2—C82.00 (14)O4—C10—C11—C3557.29 (15)
C6—N1—N2—C8176.81 (11)C12—C10—C11—C35179.82 (11)
C11—N3—N4—C123.32 (15)C9—C10—C11—C3563.33 (15)
C11—N3—N4—C13178.24 (11)N3—N4—C12—O2174.88 (13)
C6—C1—C2—C30.8 (2)C13—N4—C12—O20.6 (2)
C1—C2—C3—F1179.36 (14)N3—N4—C12—C104.77 (13)
C1—C2—C3—C40.9 (2)C13—N4—C12—C10179.10 (11)
F1—C3—C4—C5179.90 (13)O4—C10—C12—O252.06 (16)
C2—C3—C4—C50.4 (2)C11—C10—C12—O2175.47 (12)
C3—C4—C5—C60.3 (2)C9—C10—C12—O265.18 (15)
C4—C5—C6—C10.4 (2)O4—C10—C12—N4127.61 (10)
C4—C5—C6—N1179.47 (12)C11—C10—C12—N44.19 (12)
C2—C1—C6—C50.1 (2)C9—C10—C12—N4115.16 (10)
C2—C1—C6—N1179.99 (12)C12—N4—C13—C14158.41 (13)
C7—N1—C6—C549.72 (18)N3—N4—C13—C1415.66 (17)
N2—N1—C6—C5131.64 (12)C12—N4—C13—C1822.5 (2)
C7—N1—C6—C1130.14 (13)N3—N4—C13—C18163.43 (12)
N2—N1—C6—C148.49 (16)C18—C13—C14—C152.19 (19)
N2—N1—C7—O1176.51 (12)N4—C13—C14—C15176.88 (12)
C6—N1—C7—O14.8 (2)C13—C14—C15—C160.63 (19)
N2—N1—C7—C95.82 (13)C14—C15—C16—F2178.52 (12)
C6—N1—C7—C9172.88 (11)C14—C15—C16—C171.8 (2)
N1—N2—C8—C31179.34 (10)F2—C16—C17—C18177.67 (12)
N1—N2—C8—C93.06 (13)C15—C16—C17—C182.7 (2)
C19—O3—C9—C874.67 (13)C16—C17—C18—C131.0 (2)
C19—O3—C9—C742.71 (14)C14—C13—C18—C171.3 (2)
C19—O3—C9—C10162.22 (10)N4—C13—C18—C17177.73 (12)
N2—C8—C9—O3130.90 (11)C9—O3—C19—C2025.83 (17)
C31—C8—C9—O351.53 (15)C9—O3—C19—C24156.49 (11)
N2—C8—C9—C76.20 (12)O3—C19—C20—C21176.32 (11)
C31—C8—C9—C7176.23 (10)C24—C19—C20—C211.21 (19)
N2—C8—C9—C10108.96 (11)C19—C20—C21—C220.1 (2)
C31—C8—C9—C1068.62 (13)C20—C21—C22—C231.0 (2)
O1—C7—C9—O349.90 (16)C21—C22—C23—C241.0 (2)
N1—C7—C9—O3132.39 (10)C22—C23—C24—C190.0 (2)
O1—C7—C9—C8175.51 (12)O3—C19—C24—C23176.61 (11)
N1—C7—C9—C86.79 (11)C20—C19—C24—C231.18 (18)
O1—C7—C9—C1067.71 (15)C10—O4—C25—C26139.56 (11)
N1—C7—C9—C10109.99 (10)C10—O4—C25—C3044.49 (16)
C25—O4—C10—C1144.64 (14)C30—C25—C26—C270.73 (19)
C25—O4—C10—C1270.74 (13)O4—C25—C26—C27176.81 (12)
C25—O4—C10—C9169.63 (9)C25—C26—C27—C280.2 (2)
O3—C9—C10—O463.88 (10)C26—C27—C28—C290.7 (2)
C8—C9—C10—O462.43 (11)C27—C28—C29—C300.4 (2)
C7—C9—C10—O4172.73 (9)C26—C25—C30—C291.0 (2)
O3—C9—C10—C1162.11 (11)O4—C25—C30—C29176.74 (12)
C8—C9—C10—C11171.58 (9)C28—C29—C30—C250.4 (2)
C7—C9—C10—C1161.28 (11)N2—C8—C31—C3224.85 (17)
O3—C9—C10—C12173.38 (9)C9—C8—C31—C32157.85 (11)
C8—C9—C10—C1260.31 (11)C8—C31—C32—C3369.65 (14)
C7—C9—C10—C1249.99 (11)C8—C31—C32—C34168.49 (10)
N4—N3—C11—C35177.20 (11)N3—C11—C35—C3627.87 (18)
N4—N3—C11—C100.15 (14)C10—C11—C35—C36155.11 (11)
O4—C10—C11—N3125.42 (11)C11—C35—C36—C3769.94 (15)
C12—C10—C11—N32.52 (13)C11—C35—C36—C38167.73 (12)
C9—C10—C11—N3113.96 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N2C8 double bond. Cg3 and Cg5 are the centroids of the C1–C6 and C19–C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15A···Cg5i0.932.823.6941 (14)157
C20—H20A···Cg10.932.542.9632 (12)135
C29—H29A···Cg3ii0.932.823.4701 (15)128
C36—H36A···Cg3i0.982.913.7529 (15)145
Symmetry codes: (i) x, y1/2, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC38H36F2N4O4
Mr650.71
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)11.3875 (5), 11.4582 (5), 13.4885 (6)
β (°) 109.752 (1)
V3)1656.43 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.53 × 0.21 × 0.14
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.953, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
26247, 6956, 6490
Rint0.033
(sin θ/λ)max1)0.787
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.03
No. of reflections6956
No. of parameters437
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N2C8 double bond. Cg3 and Cg5 are the centroids of the C1–C6 and C19–C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15A···Cg5i0.932.823.6941 (14)157
C20—H20A···Cg10.932.542.9632 (12)135
C29—H29A···Cg3ii0.932.823.4701 (15)128
C36—H36A···Cg3i0.982.913.7529 (15)145
Symmetry codes: (i) x, y1/2, z; (ii) x, y1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVenkat Ragavan, R., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur.J. Med. Chem. 44, 3852–3857.  CrossRef CAS Google Scholar
First citationVenkat Ragavan, R., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur.J. Med. Chem. 45, 1173–1180.  Google Scholar

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Volume 67| Part 5| May 2011| Page o1036
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