(3aR,6aR)-1-Phenyl-5-[(R)-1-phenyl­ethyl]-3-[4-(trifluoro­meth­yl)phen­yl]-1,6a-dihydro­pyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione

Fronczek, C.F.; Dürüst, Y.; Yildirim, M.; Fronczek, F.R.

doi:10.1107/S1600536809049319

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3196-o3197

doi:10.1107/S1600536809049319

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(3aR,6aR)-1-Phenyl-5-[(R)-1-phenylethyl]-3-[4-(trifluoromethyl)phenyl]-1,6a-dihydropyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione

Chris F. Fronczek,^a Yaşar Dürüst,^b Muhammet Yildirim ^b and Frank R. Fronczek ^a ^*

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA, and ^bDepartment of Chemistry, Abant Izzet Baysal University, TR-14280 Bolu, Turkey
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 11 November 2009; accepted 18 November 2009; online 25 November 2009)

In the title molecule, C₂₆H₂₀F₃N₃O₂, the two central five-membered rings form a dihedral angle of 62.94 (8)°. The absolute configuration was determined by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y = −0.05 (11). Notable intra- and intermolecular contacts include C—H⋯O and C—H⋯π(arene) hydrogen bonds.

Related literature

For cycloaddition reactions of chiral maleimides with dipolar compounds, see: Bienayme (1997 ); Blanarikova et al. (2001 ); Chihab-Eddine et al. (2001 ); Oishi et al. (1993 , 1999 , 2007 ); Ondrus & Fisera (1997 ); Tokioka et al. (1997 ). For the determination of the absolute configuration by Bayesian analysis of Bijvoet differences, see: Hooft et al. (2008 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For related structures, see: Hursthouse et al. (2003 ); Skof et al. (1998 ); Fronczek et al. (2009 ).

Experimental

Crystal data

C₂₆H₂₀F₃N₃O₂
M_r = 463.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7982 (15) Å
b = 9.3064 (15) Å
c = 25.992 (4) Å
V = 2128.2 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.93 mm⁻¹
T = 90 K
0.30 × 0.18 × 0.03 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.767, T_max = 0.972
20719 measured reflections
3822 independent reflections
2959 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.108
S = 1.03
3822 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1590 Friedel pairs
Flack parameter: −0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1	1.00	2.47	2.859 (4)	103
C8—H8⋯Cg1ⁱ	0.95	2.58	3.491 (3)	161
Symmetry code: (i) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of the C19–C24 ring.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049319/bx2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049319/bx2247Isup2.hkl

checkCIF report

Comment top

There are few examples of cycloaddition reactions of chiral maleimides with dipolar compounds like nitrones, nitriloxides and anthrones reported in the literature (Bienayme, 1997; Blanarikova et al., 2001; Chihab-Eddine et al., 2001; Oishi et al., 1993; 1999; 2007; Ondrus & Fisera, 1997; Tokioka et al., 1997). Apparently, the only previously-reported example of 1,3-dipolar cycloaddition of C,N-substituted nitrilimines to chiral maleimide, (R)—N-(1-phenylethyl) maleimide is our previous work (Fronczek et al., 2009). Herein, we report the synthesis, characterization and crystal structure of the diastereomer obtained from the above reaction.

The two 5-membered rings at the core of this molecule are essentially planar and form a dihedral angle of 62.94 (8)°. The mean deviation of the seven pyrrolidine-2,5-dione atoms from their least-squares plane is 0.021 Å, and the mean deviation for the 4,5-dihydro-1H-pyrazole ring is 0.013 Å. Atom N2 deviates most from the 4,5-dihydro-1H-pyrazole ring, with deviation 0.0198 (17) Å. Atom N1 deviates most from the pyrrolidine-2,5-dione ring, with deviation 0.0610 (19) Å. The core of this structure is nearly identical to that found in a recently-reported compound produced in a similar reaction (Fronczek et al., 2009), except that it was the diastereomer with N2 and C5 swapped, and p-acetate substituent on phenyl rather than CF₃. That compound had dihedral angle between the two 5-membered rings 63.66 (4)°. Similar results can also be found in compounds having refcodes CIRFEP and WIQBIH from the Cambridge Structural Database (Allen, 2002, version 5.30, Nov. 2008). In CIRFEP (Hursthouse et al., 2003), the dihedral angle between the central ring planes is 63.65 (9)°, for one of two independent molecules and 64.23 (9)° for the other. For WIQBIH, (Skof et al., 1998), the dihedral angle formed by the central ring planes 65.99 (6)°. Notable intra and intermolecular contacts include C—H···O and C—H···π(arene) hydrogen bonds, Table 1.

The absolute configuration, based on resonant scattering of the light atoms, was slightly ambiguous from of the Flack (1983) parameter, x = -0.2 (2). Analysis of the Bijvoet pairs using the method of Hooft et al. (2008) yielded a more decisive y = -0.10 (7), corresponding to a probability P2(true) = 1.000 for this structure, confirming the absolute configuration. It agrees with that of the starting materials.

Related literature top

For cycloaddition reactions of chiral maleimides with dipolar compounds, see: Bienayme (1997); Blanarikova et al. (2001); Chihab-Eddine et al. (2001); Oishi et al. (1993, 1999, 2007); Ondrus & Fisera (1997); Tokioka et al. (1997). For the determination of the absolute configuration by Bayesian analysis of Bijvoet differences, see: Hooft et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002). For related structures, see: Hursthouse et al. (2003); Skof et al. (1998); Fronczek et al. (2009). Cg1 is the centroid of the C19–C24 ring.

Experimental top

C-(4-Trifluoromethyl)-N-phenyl hydrazonyl chloride 1 (0,149 g, 0.5 mmol) and (R)—N-(1-phenylethyl) maleimide 2 (0,100 g, 0.5 mmol) were dissolved in dry acetonitrile (20 ml). Et₃N (0.404 g, 4 mmol) was added dropwise into the mixture with stirring and after addition was completed, the reaction mixture was stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC. When the starting materials disappeared, the solvent, CH₃CN was evaporated under the reduced pressure and the crude reaction mixture was taken into water (50 ml) to remove Et₃N.HCl. The crude precipitated product was filtered and washed thoroughly with water, then n-hexane and dried under vacuum. After purification on a Chromatotron (Centrifugal Thin-Layer Chromatograph) using n-hexane-ethyl acetate (2:1) as eluant and recrystallization from acetic acid yielded cycloadduct 3.

Light green needle crystals. (161 mg, 70%). [α]^21°C₅₈₉ = +12.0° (c= 0.01 g/ml, l=10 cm, acetone). M.p. 174–176°C. R_f: 0.68 (ethyl acetate-n-hexane; 1:2). IR (KBr): ν = 3452, 3064, 2941 (C—H), 1708 (Cδb O),1599 (Cδb N), 1500, 1327, 1193, 1166, 1068, 844, 750, 696 cm^{-1. 1}H NMR (400 MHz, CDCl₃): δ= 8.17 (q, J=3.8 Hz 2H), 7.70 (t, J=4.7 Hz, 2H), 7.61 (t, J=7.6 Hz, 2H), 7.47 (t, J=6.5 Hz 2H), 7.28–7.41 (m, 5H), 7.05 (t, J=7.0, 1H), 5.44 (t, J=7.0 Hz 1H), 5.08–5.20 (dd, J=35.9 11.0 Hz 1H), 4.76–4.85 (dd, J=23.2 11.0 Hz 1H), 1.82 (t, J=7.3 Hz 3H). ¹³C NMR (100 MHz,CDCl₃): δ=172.1(Cδb O), 171.4 (Cδb O),143.9 (Cδb N), 141.2, 138.6, 133.8, 130.9, 129.3, 128.6, 128.3, 127.6, 127.1, 125.5 (–CF₃), 122.6, 121.9, 114.5, 65.3 (–CH), 52.9 (–CH), 51.6 (–CH), 16.4 (–CH₃). GC—MS (70 eV): (m/z, %)= 463 (100) [M]⁺, 359 (80), 315 (30), 269 (10), 105 (40), 70 (43). Anal Calcd for C₂₆H₂₀F₃N₃O₂ C, 67.38; H, 4.35; N, 9.07; found C, 66.45; H, 4.50; N, 8.74.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level, with H atoms having arbitrary radius.
	Fig. 2. The formation of the title compound.

(3aR,6aR)-1-Phenyl-5-[(R)-1-phenylethyl]-3-[4-(trifluoromethyl)phenyl]-1,6a-dihydropyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione top

Crystal data top

C₂₆H₂₀F₃N₃O₂	F(000) = 960
M_r = 463.45	D_x = 1.446 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3807 reflections
a = 8.7982 (15) Å	θ = 3.4–65.8°
b = 9.3064 (15) Å	µ = 0.93 mm⁻¹
c = 25.992 (4) Å	T = 90 K
V = 2128.2 (6) Å³	Lath, colourless
Z = 4	0.30 × 0.18 × 0.03 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	2959 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
phi and ω scans	θ_max = 68.9°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.767, T_max = 0.972	k = −9→10
20719 measured reflections	l = −30→31

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0512P)² + 0.4052P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.31 e Å⁻³
3822 reflections	Δρ_min = −0.18 e Å⁻³
309 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0034 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1590 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.2 (2)

Crystal data top

C₂₆H₂₀F₃N₃O₂	V = 2128.2 (6) Å³
M_r = 463.45	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.7982 (15) Å	µ = 0.93 mm⁻¹
b = 9.3064 (15) Å	T = 90 K
c = 25.992 (4) Å	0.30 × 0.18 × 0.03 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3822 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2959 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.972	R_int = 0.069
20719 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.108	Δρ_max = 0.31 e Å⁻³
S = 1.03	Δρ_min = −0.18 e Å⁻³
3822 reflections	Absolute structure: Flack (1983), 1590 Friedel pairs
309 parameters	Absolute structure parameter: −0.2 (2)
0 restraints

Special details top

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) top

	x	y	z	U_iso*/U_eq
F1	0.2050 (3)	−0.3740 (2)	0.74363 (8)	0.0649 (7)
F2	0.0123 (2)	−0.2462 (3)	0.76478 (7)	0.0556 (6)
F3	0.2228 (2)	−0.2229 (2)	0.80549 (7)	0.0451 (5)
O1	0.4288 (2)	0.4051 (2)	0.67014 (8)	0.0321 (5)
O2	0.5158 (2)	0.4981 (2)	0.49986 (8)	0.0312 (5)
N1	0.4518 (3)	0.4819 (2)	0.58594 (9)	0.0251 (5)
N2	0.4312 (3)	0.1795 (2)	0.51974 (9)	0.0254 (6)
N3	0.3502 (3)	0.0970 (2)	0.55431 (9)	0.0242 (5)
C1	0.4613 (3)	0.3818 (3)	0.62588 (12)	0.0278 (6)
C2	0.5047 (3)	0.4301 (3)	0.53947 (12)	0.0278 (7)
C3	0.5441 (3)	0.2709 (3)	0.54625 (11)	0.0252 (6)
H3	0.6507	0.2485	0.5357	0.030*
C4	0.5150 (3)	0.2394 (3)	0.60326 (11)	0.0270 (6)
H4	0.6076	0.2018	0.6210	0.032*
C5	0.3890 (3)	0.1289 (3)	0.60086 (11)	0.0253 (6)
C6	0.4527 (3)	0.1235 (3)	0.46979 (11)	0.0239 (6)
C7	0.3790 (3)	−0.0028 (3)	0.45435 (11)	0.0265 (6)
H7	0.3155	−0.0533	0.4777	0.032*
C8	0.3995 (3)	−0.0536 (3)	0.40461 (11)	0.0284 (7)
H8	0.3496	−0.1392	0.3941	0.034*
C9	0.4919 (3)	0.0190 (3)	0.37010 (12)	0.0315 (7)
H9	0.5066	−0.0172	0.3363	0.038*
C10	0.5626 (4)	0.1450 (3)	0.38552 (11)	0.0310 (7)
H10	0.6254	0.1954	0.3619	0.037*
C11	0.5429 (3)	0.1988 (3)	0.43503 (11)	0.0281 (7)
H11	0.5906	0.2860	0.4450	0.034*
C12	0.3202 (4)	0.0518 (3)	0.64432 (11)	0.0274 (7)
C13	0.3844 (4)	0.0538 (3)	0.69304 (11)	0.0312 (7)
H13	0.4651	0.1185	0.7003	0.037*
C14	0.3318 (4)	−0.0378 (3)	0.73130 (11)	0.0321 (7)
H14	0.3778	−0.0376	0.7644	0.039*
C15	0.2117 (4)	−0.1294 (3)	0.72079 (11)	0.0301 (7)
C16	0.1408 (3)	−0.1260 (3)	0.67349 (11)	0.0302 (7)
H16	0.0559	−0.1865	0.6671	0.036*
C17	0.1931 (3)	−0.0344 (3)	0.63522 (11)	0.0279 (7)
H17	0.1425	−0.0304	0.6030	0.033*
C18	0.3916 (3)	0.6287 (3)	0.59575 (12)	0.0277 (7)
H18	0.3286	0.6223	0.6277	0.033*
C19	0.5216 (3)	0.7315 (3)	0.60757 (11)	0.0260 (6)
C20	0.5713 (3)	0.7462 (3)	0.65816 (12)	0.0310 (7)
H20	0.5256	0.6896	0.6843	0.037*
C21	0.6860 (4)	0.8416 (3)	0.67111 (13)	0.0355 (8)
H21	0.7179	0.8506	0.7059	0.043*
C22	0.7537 (3)	0.9240 (3)	0.63311 (13)	0.0361 (8)
H22	0.8316	0.9904	0.6418	0.043*
C23	0.7077 (4)	0.9093 (3)	0.58217 (13)	0.0338 (7)
H23	0.7553	0.9648	0.5561	0.041*
C24	0.5922 (3)	0.8135 (3)	0.56927 (12)	0.0280 (7)
H24	0.5613	0.8039	0.5344	0.034*
C25	0.2853 (4)	0.6748 (3)	0.55281 (12)	0.0313 (7)
H25A	0.3429	0.6852	0.5208	0.047*
H25B	0.2383	0.7670	0.5617	0.047*
H25C	0.2059	0.6021	0.5482	0.047*
C26	0.1630 (4)	−0.2415 (4)	0.75849 (12)	0.0402 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.110 (2)	0.0300 (11)	0.0548 (13)	0.0067 (13)	0.0139 (13)	0.0070 (10)
F2	0.0414 (13)	0.0789 (16)	0.0464 (12)	−0.0149 (12)	−0.0022 (9)	0.0186 (11)
F3	0.0419 (12)	0.0597 (13)	0.0336 (10)	0.0020 (10)	−0.0040 (8)	0.0095 (9)
O1	0.0368 (13)	0.0260 (12)	0.0335 (12)	0.0022 (10)	−0.0047 (10)	−0.0027 (9)
O2	0.0277 (11)	0.0264 (11)	0.0394 (12)	−0.0006 (9)	0.0035 (9)	0.0002 (9)
N1	0.0242 (13)	0.0189 (13)	0.0322 (13)	0.0008 (10)	−0.0027 (10)	−0.0019 (10)
N2	0.0193 (12)	0.0227 (13)	0.0343 (13)	−0.0037 (10)	0.0008 (10)	−0.0049 (10)
N3	0.0186 (13)	0.0184 (13)	0.0356 (13)	0.0004 (10)	0.0021 (10)	0.0014 (10)
C1	0.0204 (15)	0.0238 (16)	0.0391 (17)	0.0026 (13)	−0.0037 (12)	−0.0027 (13)
C2	0.0189 (16)	0.0257 (16)	0.0387 (17)	−0.0009 (13)	−0.0013 (13)	−0.0058 (13)
C3	0.0156 (14)	0.0202 (15)	0.0397 (16)	−0.0008 (12)	−0.0007 (12)	−0.0054 (12)
C4	0.0232 (16)	0.0215 (15)	0.0361 (15)	0.0047 (13)	−0.0050 (12)	−0.0026 (13)
C5	0.0184 (15)	0.0230 (15)	0.0343 (16)	0.0052 (12)	−0.0034 (12)	−0.0021 (13)
C6	0.0173 (14)	0.0202 (15)	0.0342 (15)	0.0008 (12)	0.0000 (11)	−0.0029 (12)
C7	0.0193 (15)	0.0217 (15)	0.0385 (17)	−0.0025 (13)	0.0023 (12)	0.0005 (13)
C8	0.0256 (17)	0.0212 (16)	0.0384 (17)	−0.0020 (12)	−0.0007 (13)	−0.0044 (12)
C9	0.0281 (17)	0.0299 (18)	0.0366 (16)	−0.0020 (14)	0.0015 (13)	−0.0022 (13)
C10	0.0267 (17)	0.0288 (17)	0.0376 (17)	−0.0027 (14)	0.0029 (13)	0.0025 (13)
C11	0.0215 (15)	0.0234 (16)	0.0394 (17)	−0.0035 (13)	0.0006 (13)	−0.0021 (12)
C12	0.0298 (17)	0.0199 (15)	0.0324 (16)	0.0069 (12)	−0.0015 (13)	0.0002 (12)
C13	0.0306 (17)	0.0242 (17)	0.0388 (17)	0.0004 (14)	−0.0054 (14)	−0.0065 (13)
C14	0.0349 (19)	0.0285 (17)	0.0329 (17)	0.0058 (14)	−0.0038 (14)	−0.0015 (13)
C15	0.0307 (18)	0.0284 (17)	0.0311 (15)	0.0043 (15)	−0.0005 (13)	0.0027 (14)
C16	0.0245 (16)	0.0279 (17)	0.0382 (17)	0.0013 (14)	0.0028 (13)	−0.0002 (14)
C17	0.0251 (16)	0.0282 (17)	0.0304 (16)	0.0037 (13)	0.0003 (13)	0.0002 (13)
C18	0.0256 (16)	0.0201 (15)	0.0373 (16)	0.0053 (13)	−0.0006 (13)	−0.0041 (13)
C19	0.0212 (15)	0.0159 (14)	0.0408 (16)	0.0056 (12)	−0.0040 (12)	−0.0036 (12)
C20	0.0296 (17)	0.0255 (16)	0.0380 (17)	0.0054 (14)	−0.0006 (13)	−0.0045 (13)
C21	0.0290 (18)	0.0323 (19)	0.0452 (19)	0.0071 (15)	−0.0062 (15)	−0.0105 (15)
C22	0.0233 (17)	0.0250 (17)	0.060 (2)	−0.0008 (14)	−0.0023 (15)	−0.0122 (15)
C23	0.0255 (17)	0.0242 (17)	0.052 (2)	0.0040 (14)	0.0048 (14)	−0.0017 (14)
C24	0.0233 (16)	0.0233 (16)	0.0373 (17)	0.0049 (13)	−0.0017 (13)	−0.0023 (12)
C25	0.0278 (17)	0.0238 (16)	0.0424 (18)	0.0029 (14)	−0.0029 (14)	−0.0014 (13)
C26	0.045 (2)	0.042 (2)	0.0335 (17)	−0.0040 (17)	−0.0003 (15)	0.0002 (16)

Geometric parameters (Å, º) top

F1—C26	1.344 (4)	C11—H11	0.9500
F2—C26	1.337 (4)	C12—C13	1.387 (4)
F3—C26	1.342 (4)	C12—C17	1.396 (4)
O1—C1	1.205 (3)	C13—C14	1.390 (4)
O2—C2	1.213 (4)	C13—H13	0.9500
N1—C2	1.381 (4)	C14—C15	1.385 (5)
N1—C1	1.397 (4)	C14—H14	0.9500
N1—C18	1.487 (4)	C15—C16	1.379 (4)
N2—N3	1.381 (3)	C15—C26	1.494 (4)
N2—C6	1.412 (4)	C16—C17	1.389 (4)
N2—C3	1.477 (4)	C16—H16	0.9500
N3—C5	1.292 (4)	C17—H17	0.9500
C1—C4	1.525 (4)	C18—C25	1.519 (4)
C2—C3	1.532 (4)	C18—C19	1.523 (4)
C3—C4	1.532 (4)	C18—H18	1.0000
C3—H3	1.0000	C19—C20	1.393 (4)
C4—C5	1.514 (4)	C19—C24	1.400 (4)
C4—H4	1.0000	C20—C21	1.386 (4)
C5—C12	1.469 (4)	C20—H20	0.9500
C6—C11	1.392 (4)	C21—C22	1.385 (4)
C6—C7	1.401 (4)	C21—H21	0.9500
C7—C8	1.388 (4)	C22—C23	1.391 (4)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.386 (4)	C23—C24	1.392 (4)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.386 (4)	C24—H24	0.9500
C9—H9	0.9500	C25—H25A	0.9800
C10—C11	1.391 (4)	C25—H25B	0.9800
C10—H10	0.9500	C25—H25C	0.9800

C2—N1—C1	113.4 (2)	C12—C13—H13	119.7
C2—N1—C18	126.2 (2)	C14—C13—H13	119.7
C1—N1—C18	120.4 (2)	C15—C14—C13	119.4 (3)
N3—N2—C6	117.5 (2)	C15—C14—H14	120.3
N3—N2—C3	111.3 (2)	C13—C14—H14	120.3
C6—N2—C3	123.5 (2)	C16—C15—C14	120.4 (3)
C5—N3—N2	110.2 (2)	C16—C15—C26	118.1 (3)
O1—C1—N1	125.1 (3)	C14—C15—C26	121.3 (3)
O1—C1—C4	126.7 (3)	C15—C16—C17	120.2 (3)
N1—C1—C4	108.1 (2)	C15—C16—H16	119.9
O2—C2—N1	126.0 (3)	C17—C16—H16	119.9
O2—C2—C3	125.8 (3)	C16—C17—C12	119.8 (3)
N1—C2—C3	108.3 (3)	C16—C17—H17	120.1
N2—C3—C2	110.5 (2)	C12—C17—H17	120.1
N2—C3—C4	103.2 (2)	N1—C18—C25	110.7 (2)
C2—C3—C4	105.0 (2)	N1—C18—C19	110.2 (2)
N2—C3—H3	112.5	C25—C18—C19	115.7 (2)
C2—C3—H3	112.5	N1—C18—H18	106.6
C4—C3—H3	112.5	C25—C18—H18	106.6
C5—C4—C1	112.3 (2)	C19—C18—H18	106.6
C5—C4—C3	102.2 (2)	C20—C19—C24	118.6 (3)
C1—C4—C3	105.0 (2)	C20—C19—C18	119.2 (3)
C5—C4—H4	112.2	C24—C19—C18	122.2 (3)
C1—C4—H4	112.2	C21—C20—C19	121.4 (3)
C3—C4—H4	112.2	C21—C20—H20	119.3
N3—C5—C12	119.9 (3)	C19—C20—H20	119.3
N3—C5—C4	112.9 (3)	C22—C21—C20	119.7 (3)
C12—C5—C4	127.0 (3)	C22—C21—H21	120.2
C11—C6—C7	120.0 (3)	C20—C21—H21	120.2
C11—C6—N2	119.2 (3)	C21—C22—C23	119.9 (3)
C7—C6—N2	120.8 (3)	C21—C22—H22	120.0
C8—C7—C6	119.5 (3)	C23—C22—H22	120.0
C8—C7—H7	120.2	C22—C23—C24	120.3 (3)
C6—C7—H7	120.2	C22—C23—H23	119.9
C9—C8—C7	120.8 (3)	C24—C23—H23	119.9
C9—C8—H8	119.6	C23—C24—C19	120.1 (3)
C7—C8—H8	119.6	C23—C24—H24	119.9
C8—C9—C10	119.2 (3)	C19—C24—H24	119.9
C8—C9—H9	120.4	C18—C25—H25A	109.5
C10—C9—H9	120.4	C18—C25—H25B	109.5
C9—C10—C11	121.1 (3)	H25A—C25—H25B	109.5
C9—C10—H10	119.5	C18—C25—H25C	109.5
C11—C10—H10	119.5	H25A—C25—H25C	109.5
C10—C11—C6	119.3 (3)	H25B—C25—H25C	109.5
C10—C11—H11	120.3	F2—C26—F3	106.4 (3)
C6—C11—H11	120.3	F2—C26—F1	106.1 (3)
C13—C12—C17	119.3 (3)	F3—C26—F1	105.8 (3)
C13—C12—C5	121.8 (3)	F2—C26—C15	112.8 (3)
C17—C12—C5	118.7 (3)	F3—C26—C15	113.2 (3)
C12—C13—C14	120.6 (3)	F1—C26—C15	111.9 (3)

C6—N2—N3—C5	154.5 (3)	C8—C9—C10—C11	0.4 (5)
C3—N2—N3—C5	3.9 (3)	C9—C10—C11—C6	1.0 (5)
C2—N1—C1—O1	176.3 (3)	C7—C6—C11—C10	−1.9 (4)
C18—N1—C1—O1	−2.8 (4)	N2—C6—C11—C10	−179.1 (3)
C2—N1—C1—C4	−5.3 (3)	N3—C5—C12—C13	162.7 (3)
C18—N1—C1—C4	175.6 (2)	C4—C5—C12—C13	−12.0 (5)
C1—N1—C2—O2	−175.9 (3)	N3—C5—C12—C17	−12.5 (4)
C18—N1—C2—O2	3.1 (5)	C4—C5—C12—C17	172.8 (3)
C1—N1—C2—C3	5.2 (3)	C17—C12—C13—C14	5.6 (4)
C18—N1—C2—C3	−175.8 (3)	C5—C12—C13—C14	−169.6 (3)
N3—N2—C3—C2	−115.0 (3)	C12—C13—C14—C15	−1.5 (5)
C6—N2—C3—C2	96.5 (3)	C13—C14—C15—C16	−2.5 (5)
N3—N2—C3—C4	−3.1 (3)	C13—C14—C15—C26	172.8 (3)
C6—N2—C3—C4	−151.7 (2)	C14—C15—C16—C17	2.5 (5)
O2—C2—C3—N2	−71.1 (4)	C26—C15—C16—C17	−173.0 (3)
N1—C2—C3—N2	107.8 (3)	C15—C16—C17—C12	1.6 (4)
O2—C2—C3—C4	178.2 (3)	C13—C12—C17—C16	−5.6 (4)
N1—C2—C3—C4	−2.9 (3)	C5—C12—C17—C16	169.7 (3)
O1—C1—C4—C5	71.2 (4)	C2—N1—C18—C25	43.8 (4)
N1—C1—C4—C5	−107.2 (3)	C1—N1—C18—C25	−137.3 (3)
O1—C1—C4—C3	−178.5 (3)	C2—N1—C18—C19	−85.4 (3)
N1—C1—C4—C3	3.1 (3)	C1—N1—C18—C19	93.5 (3)
N2—C3—C4—C5	1.4 (3)	N1—C18—C19—C20	−88.0 (3)
C2—C3—C4—C5	117.2 (2)	C25—C18—C19—C20	145.5 (3)
N2—C3—C4—C1	−116.0 (2)	N1—C18—C19—C24	92.7 (3)
C2—C3—C4—C1	−0.2 (3)	C25—C18—C19—C24	−33.8 (4)
N2—N3—C5—C12	−178.4 (2)	C24—C19—C20—C21	1.3 (4)
N2—N3—C5—C4	−2.9 (3)	C18—C19—C20—C21	−178.0 (3)
C1—C4—C5—N3	112.9 (3)	C19—C20—C21—C22	−0.4 (4)
C3—C4—C5—N3	0.9 (3)	C20—C21—C22—C23	−0.7 (5)
C1—C4—C5—C12	−72.1 (4)	C21—C22—C23—C24	0.9 (5)
C3—C4—C5—C12	175.9 (3)	C22—C23—C24—C19	0.1 (4)
N3—N2—C6—C11	−175.5 (3)	C20—C19—C24—C23	−1.2 (4)
C3—N2—C6—C11	−28.7 (4)	C18—C19—C24—C23	178.1 (3)
N3—N2—C6—C7	7.4 (4)	C16—C15—C26—F2	−50.1 (4)
C3—N2—C6—C7	154.2 (3)	C14—C15—C26—F2	134.5 (3)
C11—C6—C7—C8	1.4 (4)	C16—C15—C26—F3	−171.0 (3)
N2—C6—C7—C8	178.5 (3)	C14—C15—C26—F3	13.6 (5)
C6—C7—C8—C9	0.0 (4)	C16—C15—C26—F1	69.5 (4)
C7—C8—C9—C10	−0.9 (5)	C14—C15—C26—F1	−105.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1	1.00	2.47	2.859 (4)	103
C8—H8···Cg1ⁱ	0.95	2.58	3.491 (3)	161

Symmetry code: (i) −x−1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀F₃N₃O₂
M_r	463.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	90
a, b, c (Å)	8.7982 (15), 9.3064 (15), 25.992 (4)
V (Å³)	2128.2 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.30 × 0.18 × 0.03

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.767, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	20719, 3822, 2959
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.108, 1.03
No. of reflections	3822
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.18
Absolute structure	Flack (1983), 1590 Friedel pairs
Absolute structure parameter	−0.2 (2)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1	1.00	2.47	2.859 (4)	103
C8—H8···Cg1ⁱ	0.95	2.58	3.491 (3)	161

Symmetry code: (i) −x−1, y+1/2, −z+3/2.

Acknowledgements

Abant Izzet Baysal University, Directorate of Research Projects Commission (BAP grant 2007.03.03.260) and TÜBITAK (The Scientific and Technological Research Council of Turkey, grant 106 T645) are gratefully acknowledged for financial support. We also thank Rosalind Segesta for financial assistance with the open-access fee.

References

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Volume 65| Part 12| December 2009| Pages o3196-o3197

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

(3aR,6aR)-1-Phenyl-5-[(R)-1-phenyl­ethyl]-3-[4-(tri­fluoro­meth­yl)phen­yl]-1,6a-di­hydro­pyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aR,6aR)-1-Phenyl-5-[(R)-1-phenylethyl]-3-[4-(trifluoromethyl)phenyl]-1,6a-dihydropyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione