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

Fun, H.-K.; Hemamalini, M.; Venkat Ragavan, R.; Vijayakumar, V.; Venkatesh, M.

doi:10.1107/S1600536811011664

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1036

doi:10.1107/S1600536811011664

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

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a R. Venkat Ragavan,^b V. Vijayakumar ^b and M. Venkatesh ^b

^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 , 2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₃₈H₃₆F₂N₄O₄
M_r = 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 ) T_min = 0.953, T_max = 0.987
26247 measured reflections
6956 independent reflections
6490 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.38 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
C15—H15A⋯Cg5ⁱ	0.93	2.82	3.6941 (14)	157
C20—H20A⋯Cg1	0.93	2.54	2.9632 (12)	135
C29—H29A⋯Cg3ⁱⁱ	0.93	2.82	3.4701 (15)	128
C36—H36A⋯Cg3ⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011664/rz2574sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011664/rz2574Isup2.hkl

checkCIF report

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 N2═C8 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.

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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
	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

C₃₈H₃₆F₂N₄O₄	F(000) = 684
M_r = 650.71	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9923 reflections
a = 11.3875 (5) Å	θ = 2.6–33.9°
b = 11.4582 (5) Å	µ = 0.09 mm⁻¹
c = 13.4885 (6) Å	T = 100 K
β = 109.752 (1)°	Block, colourless
V = 1656.43 (13) Å³	0.53 × 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 tube	6490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 34.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.953, T_max = 0.987	k = −16→17
26247 measured reflections	l = −21→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0646P)² + 0.0777P] where P = (F_o² + 2F_c²)/3
6956 reflections	(Δ/σ)_max < 0.001
437 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₈H₃₆F₂N₄O₄	V = 1656.43 (13) Å³
M_r = 650.71	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.3875 (5) Å	µ = 0.09 mm⁻¹
b = 11.4582 (5) Å	T = 100 K
c = 13.4885 (6) Å	0.53 × 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)
T_min = 0.953, T_max = 0.987	R_int = 0.033
26247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
6956 reflections	Δρ_min = −0.19 e Å⁻³
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

	x	y	z	U_iso*/U_eq
F1	0.16157 (12)	0.88614 (12)	−0.18115 (9)	0.0445 (3)
F2	0.06578 (9)	0.23698 (10)	−0.42001 (6)	0.02846 (19)
O1	0.13281 (8)	0.47312 (9)	0.13477 (8)	0.01997 (17)
O2	0.43391 (8)	0.32469 (9)	0.06204 (7)	0.01912 (17)
O3	0.31599 (9)	0.37927 (8)	0.33952 (7)	0.01736 (16)
O4	0.43323 (8)	0.21142 (8)	0.26514 (7)	0.01669 (15)
N1	0.31858 (9)	0.55722 (10)	0.13450 (8)	0.01593 (17)
N2	0.44800 (9)	0.54499 (10)	0.19062 (8)	0.01617 (17)
N3	0.15255 (9)	0.20611 (10)	0.06656 (8)	0.01630 (17)
N4	0.23161 (9)	0.25123 (10)	0.01456 (7)	0.01599 (17)
C1	0.33645 (12)	0.64873 (14)	−0.02151 (10)	0.0223 (2)
H1A	0.4009	0.5976	−0.0188	0.027*
C2	0.29730 (14)	0.73220 (16)	−0.10091 (11)	0.0280 (3)
H2A	0.3357	0.7384	−0.1516	0.034*
C3	0.20009 (14)	0.80572 (14)	−0.10295 (11)	0.0273 (3)
C4	0.14072 (13)	0.80168 (13)	−0.02921 (11)	0.0250 (2)
H4A	0.0760	0.8527	−0.0327	0.030*
C5	0.18107 (12)	0.71836 (12)	0.05087 (10)	0.0198 (2)
H5A	0.1433	0.7135	0.1020	0.024*
C6	0.27778 (10)	0.64274 (11)	0.05391 (9)	0.01593 (19)
C7	0.24579 (10)	0.47989 (10)	0.16516 (9)	0.01526 (18)
C8	0.46309 (10)	0.45898 (10)	0.25547 (9)	0.01485 (18)
C9	0.34030 (10)	0.39846 (10)	0.24473 (8)	0.01406 (18)
C10	0.33402 (10)	0.27539 (10)	0.19366 (8)	0.01360 (17)
C11	0.20658 (10)	0.21832 (10)	0.16633 (9)	0.01466 (18)
C12	0.34409 (10)	0.28881 (11)	0.08242 (8)	0.01450 (18)
C13	0.19215 (11)	0.24391 (11)	−0.09684 (9)	0.01556 (19)
C14	0.09432 (11)	0.16901 (12)	−0.15010 (9)	0.0179 (2)
H14A	0.0581	0.1215	−0.1125	0.022*
C15	0.05129 (12)	0.16586 (13)	−0.25994 (9)	0.0208 (2)
H15A	−0.0143	0.1171	−0.2967	0.025*
C16	0.10863 (12)	0.23713 (13)	−0.31272 (9)	0.0205 (2)
C17	0.20826 (12)	0.30842 (13)	−0.26164 (9)	0.0212 (2)
H17A	0.2467	0.3528	−0.2997	0.025*
C18	0.25023 (12)	0.31284 (13)	−0.15225 (9)	0.0198 (2)
H18A	0.3164	0.3613	−0.1162	0.024*
C19	0.28076 (11)	0.47180 (11)	0.38968 (9)	0.01629 (19)
C20	0.31030 (12)	0.58837 (11)	0.38105 (10)	0.0196 (2)
H20A	0.3530	0.6100	0.3361	0.024*
C21	0.27516 (13)	0.67257 (12)	0.44059 (11)	0.0234 (2)
H21A	0.2947	0.7506	0.4353	0.028*
C22	0.21111 (13)	0.64049 (14)	0.50775 (10)	0.0250 (3)
H22A	0.1890	0.6965	0.5481	0.030*
C23	0.18034 (13)	0.52373 (14)	0.51408 (10)	0.0238 (2)
H23A	0.1363	0.5024	0.5581	0.029*
C24	0.21458 (12)	0.43851 (12)	0.45541 (9)	0.0200 (2)
H24A	0.1937	0.3607	0.4599	0.024*
C25	0.44075 (10)	0.09116 (10)	0.25076 (9)	0.01556 (19)
C26	0.47531 (12)	0.02552 (12)	0.34262 (10)	0.0199 (2)
H26A	0.4875	0.0613	0.4072	0.024*
C27	0.49152 (14)	−0.09463 (13)	0.33716 (11)	0.0251 (3)
H27A	0.5149	−0.1390	0.3985	0.030*
C28	0.47307 (13)	−0.14878 (12)	0.24071 (12)	0.0255 (3)
H28A	0.4831	−0.2291	0.2373	0.031*
C29	0.43958 (13)	−0.08168 (12)	0.14961 (11)	0.0242 (2)
H29A	0.4277	−0.1175	0.0851	0.029*
C30	0.42349 (13)	0.03901 (12)	0.15369 (10)	0.0208 (2)
H30A	0.4016	0.0837	0.0926	0.025*
C31	0.58776 (11)	0.42088 (11)	0.32904 (9)	0.0178 (2)
H31A	0.6164	0.3561	0.2970	0.021*
H31B	0.5772	0.3922	0.3931	0.021*
C32	0.69001 (11)	0.51488 (12)	0.35900 (9)	0.0180 (2)
H32A	0.6927	0.5522	0.2944	0.022*
C33	0.66345 (14)	0.60810 (14)	0.42947 (12)	0.0270 (3)
H33A	0.7272	0.6669	0.4451	0.040*
H33B	0.6627	0.5729	0.4938	0.040*
H33C	0.5837	0.6431	0.3938	0.040*
C34	0.81648 (12)	0.45735 (14)	0.41513 (11)	0.0240 (2)
H34A	0.8808	0.5156	0.4322	0.036*
H34B	0.8329	0.3998	0.3697	0.036*
H34C	0.8150	0.4205	0.4786	0.036*
C35	0.14649 (11)	0.18458 (11)	0.24507 (9)	0.0181 (2)
H35A	0.1061	0.2531	0.2611	0.022*
H35B	0.2115	0.1611	0.3095	0.022*
C36	0.04988 (12)	0.08607 (12)	0.21154 (10)	0.0205 (2)
H36A	−0.0092	0.1041	0.1414	0.025*
C37	0.11105 (18)	−0.03154 (15)	0.20684 (16)	0.0352 (3)
H37A	0.1548	−0.0271	0.1573	0.053*
H37B	0.0480	−0.0909	0.1850	0.053*
H37C	0.1688	−0.0505	0.2753	0.053*
C38	−0.02151 (14)	0.08170 (16)	0.28949 (12)	0.0294 (3)
H38A	−0.0841	0.0219	0.2684	0.044*
H38B	−0.0606	0.1558	0.2902	0.044*
H38C	0.0355	0.0647	0.3587	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0486 (6)	0.0413 (6)	0.0364 (5)	0.0022 (5)	0.0051 (4)	0.0265 (5)
F2	0.0307 (4)	0.0377 (5)	0.0146 (3)	0.0004 (4)	0.0046 (3)	0.0004 (3)
O1	0.0144 (3)	0.0176 (4)	0.0279 (4)	−0.0001 (3)	0.0071 (3)	0.0017 (4)
O2	0.0164 (3)	0.0223 (4)	0.0205 (4)	−0.0038 (3)	0.0086 (3)	−0.0024 (3)
O3	0.0251 (4)	0.0127 (3)	0.0172 (3)	−0.0003 (3)	0.0110 (3)	−0.0009 (3)
O4	0.0173 (3)	0.0116 (3)	0.0177 (3)	0.0008 (3)	0.0014 (3)	−0.0015 (3)
N1	0.0134 (4)	0.0147 (4)	0.0191 (4)	0.0004 (3)	0.0047 (3)	0.0042 (3)
N2	0.0131 (4)	0.0161 (4)	0.0180 (4)	−0.0004 (3)	0.0035 (3)	0.0008 (4)
N3	0.0153 (4)	0.0175 (4)	0.0171 (4)	−0.0022 (4)	0.0069 (3)	0.0015 (4)
N4	0.0143 (4)	0.0196 (4)	0.0139 (3)	−0.0036 (4)	0.0046 (3)	−0.0001 (3)
C1	0.0208 (5)	0.0258 (6)	0.0217 (5)	0.0003 (5)	0.0092 (4)	0.0035 (5)
C2	0.0284 (6)	0.0332 (7)	0.0229 (5)	−0.0045 (6)	0.0093 (5)	0.0075 (6)
C3	0.0276 (6)	0.0250 (6)	0.0236 (5)	−0.0036 (5)	0.0011 (5)	0.0113 (5)
C4	0.0217 (5)	0.0195 (6)	0.0302 (6)	0.0019 (5)	0.0037 (5)	0.0068 (5)
C5	0.0183 (5)	0.0173 (5)	0.0229 (5)	0.0010 (4)	0.0058 (4)	0.0026 (4)
C6	0.0158 (4)	0.0143 (4)	0.0169 (4)	−0.0010 (4)	0.0045 (3)	0.0023 (4)
C7	0.0156 (4)	0.0125 (4)	0.0185 (4)	0.0004 (4)	0.0068 (3)	0.0006 (4)
C8	0.0146 (4)	0.0128 (4)	0.0166 (4)	−0.0009 (4)	0.0045 (3)	−0.0016 (4)
C9	0.0157 (4)	0.0120 (4)	0.0153 (4)	−0.0003 (4)	0.0063 (3)	−0.0002 (4)
C10	0.0135 (4)	0.0119 (4)	0.0148 (4)	−0.0009 (3)	0.0040 (3)	−0.0011 (4)
C11	0.0156 (4)	0.0126 (4)	0.0163 (4)	−0.0014 (4)	0.0060 (3)	−0.0004 (4)
C12	0.0139 (4)	0.0146 (4)	0.0148 (4)	−0.0002 (4)	0.0046 (3)	−0.0013 (4)
C13	0.0158 (4)	0.0164 (5)	0.0138 (4)	−0.0001 (4)	0.0043 (3)	−0.0002 (4)
C14	0.0176 (5)	0.0182 (5)	0.0174 (4)	−0.0016 (4)	0.0051 (4)	−0.0008 (4)
C15	0.0202 (5)	0.0221 (6)	0.0179 (4)	−0.0014 (5)	0.0035 (4)	−0.0027 (4)
C16	0.0208 (5)	0.0248 (6)	0.0148 (4)	0.0040 (5)	0.0045 (4)	0.0003 (4)
C17	0.0220 (5)	0.0246 (6)	0.0174 (4)	0.0001 (5)	0.0073 (4)	0.0031 (5)
C18	0.0198 (5)	0.0221 (5)	0.0171 (4)	−0.0037 (4)	0.0055 (4)	0.0015 (4)
C19	0.0183 (4)	0.0152 (4)	0.0155 (4)	0.0018 (4)	0.0059 (3)	−0.0017 (4)
C20	0.0221 (5)	0.0153 (5)	0.0225 (5)	0.0000 (4)	0.0088 (4)	−0.0030 (4)
C21	0.0265 (6)	0.0176 (5)	0.0250 (5)	0.0010 (5)	0.0075 (4)	−0.0054 (5)
C22	0.0291 (6)	0.0257 (6)	0.0209 (5)	0.0082 (5)	0.0091 (4)	−0.0044 (5)
C23	0.0275 (6)	0.0270 (6)	0.0201 (5)	0.0088 (5)	0.0119 (4)	0.0032 (5)
C24	0.0235 (5)	0.0200 (5)	0.0190 (4)	0.0031 (4)	0.0101 (4)	0.0021 (4)
C25	0.0135 (4)	0.0122 (4)	0.0195 (4)	0.0007 (4)	0.0037 (3)	−0.0016 (4)
C26	0.0216 (5)	0.0147 (5)	0.0210 (5)	0.0013 (4)	0.0040 (4)	0.0000 (4)
C27	0.0251 (6)	0.0160 (5)	0.0289 (6)	0.0017 (5)	0.0022 (5)	0.0027 (5)
C28	0.0227 (6)	0.0133 (5)	0.0355 (7)	0.0020 (4)	0.0035 (5)	−0.0027 (5)
C29	0.0243 (6)	0.0171 (5)	0.0282 (6)	0.0014 (5)	0.0048 (5)	−0.0078 (5)
C30	0.0242 (5)	0.0158 (5)	0.0204 (5)	0.0018 (4)	0.0052 (4)	−0.0028 (4)
C31	0.0168 (5)	0.0136 (4)	0.0197 (4)	−0.0012 (4)	0.0016 (4)	0.0003 (4)
C32	0.0167 (4)	0.0170 (5)	0.0183 (4)	−0.0022 (4)	0.0032 (4)	−0.0001 (4)
C33	0.0255 (6)	0.0211 (6)	0.0314 (6)	−0.0036 (5)	0.0059 (5)	−0.0087 (5)
C34	0.0171 (5)	0.0246 (6)	0.0263 (5)	−0.0011 (5)	0.0021 (4)	0.0008 (5)
C35	0.0201 (5)	0.0184 (5)	0.0178 (4)	−0.0040 (4)	0.0089 (4)	0.0000 (4)
C36	0.0211 (5)	0.0201 (5)	0.0211 (5)	−0.0054 (5)	0.0080 (4)	0.0020 (4)
C37	0.0394 (8)	0.0184 (6)	0.0518 (9)	−0.0061 (6)	0.0208 (7)	−0.0006 (7)
C38	0.0266 (6)	0.0362 (8)	0.0286 (6)	−0.0095 (6)	0.0135 (5)	0.0045 (6)

Geometric parameters (Å, º) top

F1—C3	1.3570 (17)	C20—C21	1.3975 (18)
F2—C16	1.3620 (14)	C20—H20A	0.9300
O1—C7	1.2136 (14)	C21—C22	1.391 (2)
O2—C12	1.2169 (14)	C21—H21A	0.9300
O3—C19	1.3880 (15)	C22—C23	1.393 (2)
O3—C9	1.4138 (13)	C22—H22A	0.9300
O4—C25	1.3981 (15)	C23—C24	1.3930 (19)
O4—C10	1.4166 (14)	C23—H23A	0.9300
N1—C7	1.3693 (15)	C24—H24A	0.9300
N1—N2	1.4179 (14)	C25—C26	1.3879 (17)
N1—C6	1.4200 (15)	C25—C30	1.3914 (16)
N2—C8	1.2901 (15)	C26—C27	1.3943 (19)
N3—C11	1.2843 (14)	C26—H26A	0.9300
N3—N4	1.4131 (13)	C27—C28	1.392 (2)
N4—C12	1.3680 (15)	C27—H27A	0.9300
N4—C13	1.4180 (14)	C28—C29	1.389 (2)
C1—C2	1.392 (2)	C28—H28A	0.9300
C1—C6	1.3949 (17)	C29—C30	1.3985 (19)
C1—H1A	0.9300	C29—H29A	0.9300
C2—C3	1.384 (2)	C30—H30A	0.9300
C2—H2A	0.9300	C31—C32	1.5367 (17)
C3—C4	1.380 (2)	C31—H31A	0.9700
C4—C5	1.3977 (18)	C31—H31B	0.9700
C4—H4A	0.9300	C32—C33	1.5265 (19)
C5—C6	1.3910 (17)	C32—C34	1.5313 (18)
C5—H5A	0.9300	C32—H32A	0.9800
C7—C9	1.5492 (16)	C33—H33A	0.9600
C8—C31	1.4961 (16)	C33—H33B	0.9600
C8—C9	1.5232 (16)	C33—H33C	0.9600
C9—C10	1.5604 (16)	C34—H34A	0.9600
C10—C11	1.5192 (16)	C34—H34B	0.9600
C10—C12	1.5506 (15)	C34—H34C	0.9600
C11—C35	1.4956 (15)	C35—C36	1.5338 (18)
C13—C14	1.3974 (17)	C35—H35A	0.9700
C13—C18	1.3978 (17)	C35—H35B	0.9700
C14—C15	1.3949 (16)	C36—C37	1.528 (2)
C14—H14A	0.9300	C36—C38	1.5320 (18)
C15—C16	1.3836 (19)	C36—H36A	0.9800
C15—H15A	0.9300	C37—H37A	0.9600
C16—C17	1.3787 (19)	C37—H37B	0.9600
C17—C18	1.3898 (16)	C37—H37C	0.9600
C17—H17A	0.9300	C38—H38A	0.9600
C18—H18A	0.9300	C38—H38B	0.9600
C19—C20	1.3918 (18)	C38—H38C	0.9600
C19—C24	1.3969 (16)

C19—O3—C9	119.95 (10)	C22—C21—H21A	119.8
C25—O4—C10	119.19 (9)	C20—C21—H21A	119.8
C7—N1—N2	113.63 (9)	C21—C22—C23	119.47 (12)
C7—N1—C6	127.08 (10)	C21—C22—H22A	120.3
N2—N1—C6	119.28 (9)	C23—C22—H22A	120.3
C8—N2—N1	108.28 (10)	C22—C23—C24	120.93 (12)
C11—N3—N4	108.68 (9)	C22—C23—H23A	119.5
C12—N4—N3	113.12 (9)	C24—C23—H23A	119.5
C12—N4—C13	128.13 (10)	C23—C24—C19	118.93 (13)
N3—N4—C13	118.52 (9)	C23—C24—H24A	120.5
C2—C1—C6	119.15 (13)	C19—C24—H24A	120.5
C2—C1—H1A	120.4	C26—C25—C30	120.97 (11)
C6—C1—H1A	120.4	C26—C25—O4	114.99 (10)
C3—C2—C1	118.66 (12)	C30—C25—O4	123.91 (11)
C3—C2—H2A	120.7	C25—C26—C27	119.38 (12)
C1—C2—H2A	120.7	C25—C26—H26A	120.3
F1—C3—C4	118.35 (15)	C27—C26—H26A	120.3
F1—C3—C2	118.36 (14)	C28—C27—C26	120.58 (13)
C4—C3—C2	123.29 (13)	C28—C27—H27A	119.7
C3—C4—C5	117.83 (13)	C26—C27—H27A	119.7
C3—C4—H4A	121.1	C29—C28—C27	119.32 (13)
C5—C4—H4A	121.1	C29—C28—H28A	120.3
C6—C5—C4	119.90 (12)	C27—C28—H28A	120.3
C6—C5—H5A	120.0	C28—C29—C30	120.86 (13)
C4—C5—H5A	120.0	C28—C29—H29A	119.6
C5—C6—C1	121.16 (11)	C30—C29—H29A	119.6
C5—C6—N1	120.23 (10)	C25—C30—C29	118.88 (13)
C1—C6—N1	118.61 (11)	C25—C30—H30A	120.6
O1—C7—N1	128.33 (11)	C29—C30—H30A	120.6
O1—C7—C9	127.19 (11)	C8—C31—C32	115.77 (10)
N1—C7—C9	104.43 (9)	C8—C31—H31A	108.3
N2—C8—C31	123.48 (11)	C32—C31—H31A	108.3
N2—C8—C9	112.06 (10)	C8—C31—H31B	108.3
C31—C8—C9	124.40 (10)	C32—C31—H31B	108.3
O3—C9—C8	116.03 (9)	H31A—C31—H31B	107.4
O3—C9—C7	114.68 (9)	C33—C32—C34	110.15 (11)
C8—C9—C7	101.08 (9)	C33—C32—C31	111.23 (10)
O3—C9—C10	105.36 (9)	C34—C32—C31	109.31 (11)
C8—C9—C10	110.92 (9)	C33—C32—H32A	108.7
C7—C9—C10	108.72 (9)	C34—C32—H32A	108.7
O4—C10—C11	114.78 (9)	C31—C32—H32A	108.7
O4—C10—C12	114.02 (9)	C32—C33—H33A	109.5
C11—C10—C12	100.65 (9)	C32—C33—H33B	109.5
O4—C10—C9	105.08 (8)	H33A—C33—H33B	109.5
C11—C10—C9	113.18 (9)	C32—C33—H33C	109.5
C12—C10—C9	109.28 (9)	H33A—C33—H33C	109.5
N3—C11—C35	122.94 (10)	H33B—C33—H33C	109.5
N3—C11—C10	112.42 (9)	C32—C34—H34A	109.5
C35—C11—C10	124.59 (10)	C32—C34—H34B	109.5
O2—C12—N4	128.57 (10)	H34A—C34—H34B	109.5
O2—C12—C10	126.50 (10)	C32—C34—H34C	109.5
N4—C12—C10	104.92 (9)	H34A—C34—H34C	109.5
C14—C13—C18	120.75 (10)	H34B—C34—H34C	109.5
C14—C13—N4	119.55 (10)	C11—C35—C36	115.82 (10)
C18—C13—N4	119.70 (10)	C11—C35—H35A	108.3
C15—C14—C13	119.65 (11)	C36—C35—H35A	108.3
C15—C14—H14A	120.2	C11—C35—H35B	108.3
C13—C14—H14A	120.2	C36—C35—H35B	108.3
C16—C15—C14	118.28 (12)	H35A—C35—H35B	107.4
C16—C15—H15A	120.9	C37—C36—C38	110.78 (13)
C14—C15—H15A	120.9	C37—C36—C35	111.69 (11)
F2—C16—C17	118.07 (12)	C38—C36—C35	108.41 (11)
F2—C16—C15	118.95 (12)	C37—C36—H36A	108.6
C17—C16—C15	122.98 (11)	C38—C36—H36A	108.6
C16—C17—C18	118.80 (12)	C35—C36—H36A	108.6
C16—C17—H17A	120.6	C36—C37—H37A	109.5
C18—C17—H17A	120.6	C36—C37—H37B	109.5
C17—C18—C13	119.47 (12)	H37A—C37—H37B	109.5
C17—C18—H18A	120.3	C36—C37—H37C	109.5
C13—C18—H18A	120.3	H37A—C37—H37C	109.5
O3—C19—C20	125.06 (10)	H37B—C37—H37C	109.5
O3—C19—C24	114.06 (11)	C36—C38—H38A	109.5
C20—C19—C24	120.84 (11)	C36—C38—H38B	109.5
C19—C20—C21	119.35 (12)	H38A—C38—H38B	109.5
C19—C20—H20A	120.3	C36—C38—H38C	109.5
C21—C20—H20A	120.3	H38A—C38—H38C	109.5
C22—C21—C20	120.46 (13)	H38B—C38—H38C	109.5

C7—N1—N2—C8	2.00 (14)	O4—C10—C11—C35	57.29 (15)
C6—N1—N2—C8	−176.81 (11)	C12—C10—C11—C35	−179.82 (11)
C11—N3—N4—C12	3.32 (15)	C9—C10—C11—C35	−63.33 (15)
C11—N3—N4—C13	178.24 (11)	N3—N4—C12—O2	174.88 (13)
C6—C1—C2—C3	−0.8 (2)	C13—N4—C12—O2	0.6 (2)
C1—C2—C3—F1	−179.36 (14)	N3—N4—C12—C10	−4.77 (13)
C1—C2—C3—C4	0.9 (2)	C13—N4—C12—C10	−179.10 (11)
F1—C3—C4—C5	179.90 (13)	O4—C10—C12—O2	−52.06 (16)
C2—C3—C4—C5	−0.4 (2)	C11—C10—C12—O2	−175.47 (12)
C3—C4—C5—C6	−0.3 (2)	C9—C10—C12—O2	65.18 (15)
C4—C5—C6—C1	0.4 (2)	O4—C10—C12—N4	127.61 (10)
C4—C5—C6—N1	−179.47 (12)	C11—C10—C12—N4	4.19 (12)
C2—C1—C6—C5	0.1 (2)	C9—C10—C12—N4	−115.16 (10)
C2—C1—C6—N1	−179.99 (12)	C12—N4—C13—C14	158.41 (13)
C7—N1—C6—C5	49.72 (18)	N3—N4—C13—C14	−15.66 (17)
N2—N1—C6—C5	−131.64 (12)	C12—N4—C13—C18	−22.5 (2)
C7—N1—C6—C1	−130.14 (13)	N3—N4—C13—C18	163.43 (12)
N2—N1—C6—C1	48.49 (16)	C18—C13—C14—C15	−2.19 (19)
N2—N1—C7—O1	176.51 (12)	N4—C13—C14—C15	176.88 (12)
C6—N1—C7—O1	−4.8 (2)	C13—C14—C15—C16	0.63 (19)
N2—N1—C7—C9	−5.82 (13)	C14—C15—C16—F2	−178.52 (12)
C6—N1—C7—C9	172.88 (11)	C14—C15—C16—C17	1.8 (2)
N1—N2—C8—C31	−179.34 (10)	F2—C16—C17—C18	177.67 (12)
N1—N2—C8—C9	3.06 (13)	C15—C16—C17—C18	−2.7 (2)
C19—O3—C9—C8	74.67 (13)	C16—C17—C18—C13	1.0 (2)
C19—O3—C9—C7	−42.71 (14)	C14—C13—C18—C17	1.3 (2)
C19—O3—C9—C10	−162.22 (10)	N4—C13—C18—C17	−177.73 (12)
N2—C8—C9—O3	−130.90 (11)	C9—O3—C19—C20	−25.83 (17)
C31—C8—C9—O3	51.53 (15)	C9—O3—C19—C24	156.49 (11)
N2—C8—C9—C7	−6.20 (12)	O3—C19—C20—C21	−176.32 (11)
C31—C8—C9—C7	176.23 (10)	C24—C19—C20—C21	1.21 (19)
N2—C8—C9—C10	108.96 (11)	C19—C20—C21—C22	−0.1 (2)
C31—C8—C9—C10	−68.62 (13)	C20—C21—C22—C23	−1.0 (2)
O1—C7—C9—O3	−49.90 (16)	C21—C22—C23—C24	1.0 (2)
N1—C7—C9—O3	132.39 (10)	C22—C23—C24—C19	0.0 (2)
O1—C7—C9—C8	−175.51 (12)	O3—C19—C24—C23	176.61 (11)
N1—C7—C9—C8	6.79 (11)	C20—C19—C24—C23	−1.18 (18)
O1—C7—C9—C10	67.71 (15)	C10—O4—C25—C26	−139.56 (11)
N1—C7—C9—C10	−109.99 (10)	C10—O4—C25—C30	44.49 (16)
C25—O4—C10—C11	44.64 (14)	C30—C25—C26—C27	−0.73 (19)
C25—O4—C10—C12	−70.74 (13)	O4—C25—C26—C27	−176.81 (12)
C25—O4—C10—C9	169.63 (9)	C25—C26—C27—C28	−0.2 (2)
O3—C9—C10—O4	−63.88 (10)	C26—C27—C28—C29	0.7 (2)
C8—C9—C10—O4	62.43 (11)	C27—C28—C29—C30	−0.4 (2)
C7—C9—C10—O4	172.73 (9)	C26—C25—C30—C29	1.0 (2)
O3—C9—C10—C11	62.11 (11)	O4—C25—C30—C29	176.74 (12)
C8—C9—C10—C11	−171.58 (9)	C28—C29—C30—C25	−0.4 (2)
C7—C9—C10—C11	−61.28 (11)	N2—C8—C31—C32	24.85 (17)
O3—C9—C10—C12	173.38 (9)	C9—C8—C31—C32	−157.85 (11)
C8—C9—C10—C12	−60.31 (11)	C8—C31—C32—C33	69.65 (14)
C7—C9—C10—C12	49.99 (11)	C8—C31—C32—C34	−168.49 (10)
N4—N3—C11—C35	177.20 (11)	N3—C11—C35—C36	27.87 (18)
N4—N3—C11—C10	−0.15 (14)	C10—C11—C35—C36	−155.11 (11)
O4—C10—C11—N3	−125.42 (11)	C11—C35—C36—C37	69.94 (15)
C12—C10—C11—N3	−2.52 (13)	C11—C35—C36—C38	−167.73 (12)
C9—C10—C11—N3	113.96 (11)

Hydrogen-bond geometry (Å, º) top

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	D···A	D—H···A
C15—H15A···Cg5ⁱ	0.93	2.82	3.6941 (14)	157
C20—H20A···Cg1	0.93	2.54	2.9632 (12)	135
C29—H29A···Cg3ⁱⁱ	0.93	2.82	3.4701 (15)	128
C36—H36A···Cg3ⁱ	0.98	2.91	3.7529 (15)	145

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

Experimental details

Crystal data
Chemical formula	C₃₈H₃₆F₂N₄O₄
M_r	650.71
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	11.3875 (5), 11.4582 (5), 13.4885 (6)
β (°)	109.752 (1)
V (Å³)	1656.43 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.21 × 0.14

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.953, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	26247, 6956, 6490
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.787

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.03
No. of reflections	6956
No. of parameters	437
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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 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	D···A	D—H···A
C15—H15A···Cg5ⁱ	0.93	2.82	3.6941 (14)	157
C20—H20A···Cg1	0.93	2.54	2.9632 (12)	135
C29—H29A···Cg3ⁱⁱ	0.93	2.82	3.4701 (15)	128
C36—H36A···Cg3ⁱ	0.98	2.91	3.7529 (15)	145

Symmetry codes: (i) −x, y−1/2, −z; (ii) x, y−1, 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

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

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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