2,4-Diphenyl-6-trifluoro­methyl-2,3-dihydro-1H,5H-pyrrolo­[3,4-c]pyrrole-1,3-dione

Roberts, S.A.; Martinez-Ariza, G.; Dietrich, J.; Hulme, C.

doi:10.1107/S1600536812001675

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o496-o497

doi:10.1107/S1600536812001675

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2,4-Diphenyl-6-trifluoromethyl-2,3-dihydro-1H,5H-pyrrolo[3,4-c]pyrrole-1,3-dione

Sue A. Roberts,^a ^* Guillermo Martinez-Ariza,^b Justin Dietrich ^c and Christopher Hulme ^c

^aDepartment of Chemistry and Biochemistry, 1041 E. Lowell St, The University of Arizona, Tucson, AZ 85721, USA, ^bDepartamento de Quimica, Division de Ciencias Naturales y Exactas, Universidad de Guanajuato, Col. Noria Alta s/n C.P. 36050, Guanajuato, Gto., Mexico, and ^cSouthwest Center for Drug Discovery and Development, College of Pharmacy, BIO5 Institute, The University of Arizona, Tucson, AZ 85721, USA
^*Correspondence e-mail: suer@email.arizona.edu

(Received 22 November 2011; accepted 13 January 2012; online 21 January 2012)

The asymmetric unit of the title compound, C₁₉H₁₁F₃N₂O₂, contains two crystallographically unique molecules which differ in the rotation of a phenyl ring and a –CF₃ substituent. The dihedral angles involving the pyrrole ring and the attached phenyl ring are 62.82 (8) and 71.54 (7)° in the two molecules. The difference in the rotation of the CF₃ groups with respect to the pyrrolo rings to which they are attached is 23.5(1)°. For one molecule, there is a close contact between an H atom and the centroid of the phenyl ring of an adjacent molecule (2.572 Å). A similar contact is lacking in the second molecule. In the crystal, N—H⋯O interactions connect adjacent molecules into a chain normal to (01 $[\overline{1}]$ ). Crystallographically unique molecules alternate along the hydrogen-bonded chains.

Related literature

For background information on the biological activity of compounds with pyrrol-3,4-dicarboximide scaffolds, see: Malinka et al. (1999 , 2005 ); Shen et al. (2010 ). For a description of structurally similar lamellarins, see: Yu et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₁F₃N₂O₂
M_r = 356.30
Triclinic, $[P \overline 1]$
a = 10.4730 (4) Å
b = 12.2394 (5) Å
c = 13.4379 (5) Å
α = 67.542 (2)°
β = 82.511 (2)°
γ = 80.294 (2)°
V = 1564.98 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.86, T_max = 0.98
32220 measured reflections
6660 independent reflections
5882 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.089
S = 0.98
6660 reflections
469 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88	2.01	2.8395 (14)	156
N1—H1⋯O4	0.88	2.00	2.8757 (14)	173
Symmetry code: (i) x, y+1, z-1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).; software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001675/nk2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001675/nk2128Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001675/nk2128Isup3.cml

checkCIF report

Comment top

The biological activity of compounds with pyrrol-3,4-dicarboximide scaffolds includes analgesic, central nervous system depressive action, and antiproliferative activities (Malinka et al. 2005; Malinka et al. 1999; Shen et al. 2010). Furthermore, pyrrol-3,4-dicarboximides are very interesting compounds because of their structural similarity to lamellarins (Yu et al. 2011). The title compound was synthesized and its crystal structure is reported herein.

The asymmetric unit contains two molecules of the title compound (see Figure 1 for a view of the molecular structure). After overlapping the central fused ring of the independent molecules using OLEX2 (see Figure 2; Dolomanov et al., 2009), it is clear that the molecules differ only in rotation of the phenyl ring and CF₃ substituents. The phenyl ring planes differ by approximately a 41° rotation about the N—C bond. The CF₃ substituent is rotated by 16.5°. The r.m.s. deviation of atomic positions between the two molecules is 0.56 Å (all atoms), 0.065 Å for matched atoms. The center of one of the phenyl rings that differ in orientation (C7—C12) has a close contact (2.572 Å) to the hydrogen atom bonded to C14 on a symmetry related molecule. This contact is lacking for the other molecule.

Intermolecular hydrogen bonds connect molecules into a ribbon throughout the crystal. Figure 3 shows molecular packing and hydrogen bonds in the crystal. Hydrogen bonds exist between O1 and N3 (2.8395 Å) and O4 and N1 (2.8757 Å) and connect molecules into a chain normal to (0 1 - 1). Crystallographically unique molecules alternate along the hydrogen bonded chains. The graph set description is C2,2(12)>a>b (determined using Mercury (Macrae et al., 2008)).

Related literature top

For background information on the biological activity of compounds with pyrrol-3,4-dicarboximide scaffolds, see: Malinka et al. (1999, 2005); Shen et al. (2010). For a description of structurally similar lamellarins, see: Yu et al. (2011).

Experimental top

To a stirred solution of 4-phenyl-2-(trifluoromethyl) oxazol-5(4H)-one (0.3 g, 1.3 mmol) and 3-bromo-1-phenyl-1H-pyrrole-2,5-dione (0.33 g, 1.3 mmol) in toluene (20 mL), N,N-diisopropylethylamine (0.33 g, 0.45 ml, 2.6 mmol) was added at 298 K. The reaction mixture was stirred at room temperature for 15 minutes. Thereafter, the solvent was evaporated in vacuo and crude material purified by automated flash chromatography using a gradient from 100% Hexane to 70% Hexane/AcOEt. Crystals suitable for X-ray diffraction studies were obtained by recrystallization of the pure product from methylene chloride and hexane.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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), Mercury (Macrae et al., 2008) and OLEX2 (Dolomanov et al., 2009).; software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The two independent molecules in the asymmetric unit are shown. Anisotropically refined atoms are shown as 50% probability ellipsoids.
	Fig. 2. An overlay of the independent molecules in the asymmetric unit, one shown in a ball-and-stick representation, the other as wireframe. The only significant differences between the molecules are rotations of the phenyl and CF₃ substituents.
	Fig. 3. A view emphasizing chains of hydrogen bonded molecules. Hydrogen bonds are shown as blue dotted lines.

2,4-Diphenyl-6-trifluoromethyl-2,3-dihydro-1H,5H- pyrrolo[3,4-c]pyrrole-1,3-dione top

Crystal data top

C₁₉H₁₁F₃N₂O₂	Z = 4
M_r = 356.30	F(000) = 728
Triclinic, P1	D_x = 1.512 Mg m⁻³
a = 10.4730 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2394 (5) Å	Cell parameters from 9948 reflections
c = 13.4379 (5) Å	θ = 2.5–26.7°
α = 67.542 (2)°	µ = 0.12 mm⁻¹
β = 82.511 (2)°	T = 100 K
γ = 80.294 (2)°	Prismatic, white
V = 1564.98 (11) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6660 independent reflections
Radiation source: fine-focus sealed tube	5882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.3333 pixels mm^-1	θ_max = 26.8°, θ_min = 1.6°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −15→15
T_min = 0.86, T_max = 0.98	l = −17→16
32220 measured reflections

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) = 0.089	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0353P)² + 1.1733P] where P = (F_o² + 2F_c²)/3
6660 reflections	(Δ/σ)_max < 0.001
469 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₁₁F₃N₂O₂	γ = 80.294 (2)°
M_r = 356.30	V = 1564.98 (11) Å³
Triclinic, P1	Z = 4
a = 10.4730 (4) Å	Mo Kα radiation
b = 12.2394 (5) Å	µ = 0.12 mm⁻¹
c = 13.4379 (5) Å	T = 100 K
α = 67.542 (2)°	0.30 × 0.20 × 0.20 mm
β = 82.511 (2)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6660 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	5882 reflections with I > 2σ(I)
T_min = 0.86, T_max = 0.98	R_int = 0.024
32220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 0.98	Δρ_max = 0.38 e Å⁻³
6660 reflections	Δρ_min = −0.40 e Å⁻³
469 parameters

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
N1	0.35532 (11)	0.26068 (9)	0.56592 (9)	0.0148 (2)
H1	0.325	0.3322	0.5223	0.018*
N2	0.50857 (11)	−0.07836 (9)	0.78471 (9)	0.0160 (2)
F2	0.21712 (9)	0.35605 (8)	0.72938 (8)	0.0317 (2)
F3	0.14763 (10)	0.18726 (8)	0.81133 (8)	0.0427 (3)
F1	0.08781 (9)	0.30162 (10)	0.65371 (8)	0.0374 (2)
O1	0.34017 (9)	−0.03336 (8)	0.89917 (8)	0.0201 (2)
O2	0.65695 (9)	−0.06867 (8)	0.63809 (8)	0.0202 (2)
C12	0.63795 (13)	0.15446 (12)	0.41080 (11)	0.0177 (3)
H12	0.6364	0.0713	0.4483	0.021*
C1	0.30092 (12)	0.20234 (11)	0.66742 (10)	0.0152 (3)
C6	0.46392 (12)	0.19190 (11)	0.54172 (10)	0.0143 (2)
C3	0.39775 (12)	−0.00958 (11)	0.81056 (10)	0.0151 (3)
C2	0.37467 (12)	0.09388 (11)	0.70964 (10)	0.0148 (2)
C7	0.55052 (12)	0.23597 (11)	0.44434 (10)	0.0152 (3)
C4	0.56091 (12)	−0.02501 (11)	0.67653 (10)	0.0152 (3)
C5	0.47444 (12)	0.08653 (11)	0.63056 (10)	0.0141 (2)
C13	0.56303 (13)	−0.19193 (11)	0.85754 (11)	0.0171 (3)
C8	0.55377 (13)	0.35825 (12)	0.38800 (11)	0.0182 (3)
H8	0.4948	0.4143	0.4099	0.022*
C9	0.64284 (14)	0.39777 (13)	0.30042 (11)	0.0220 (3)
H9	0.6443	0.4809	0.2623	0.026*
C14	0.56688 (14)	−0.29193 (12)	0.83170 (12)	0.0214 (3)
H14	0.5332	−0.2851	0.767	0.026*
C11	0.72685 (14)	0.19496 (13)	0.32298 (11)	0.0218 (3)
H11	0.7857	0.1394	0.3004	0.026*
C18	0.61225 (15)	−0.20018 (13)	0.95143 (12)	0.0243 (3)
H18	0.6099	−0.1312	0.9683	0.029*
C10	0.72999 (14)	0.31659 (13)	0.26804 (11)	0.0232 (3)
H10	0.7916	0.3441	0.2085	0.028*
C15	0.62048 (15)	−0.40205 (13)	0.90134 (13)	0.0279 (3)
H15	0.6235	−0.4711	0.8844	0.034*
C16	0.66956 (16)	−0.41145 (14)	0.99549 (13)	0.0323 (4)
H16	0.7063	−0.4869	1.043	0.039*
C17	0.66517 (17)	−0.31135 (15)	1.02056 (12)	0.0326 (4)
H17	0.6985	−0.3185	1.0855	0.039*
C19	0.18769 (13)	0.26076 (12)	0.71546 (11)	0.0189 (3)
F4	0.44762 (10)	0.84161 (10)	0.14618 (8)	0.0383 (3)
F5	0.31060 (9)	0.84493 (9)	0.27591 (8)	0.0373 (2)
F6	0.44468 (11)	0.68802 (9)	0.29453 (10)	0.0485 (3)
O4	0.25551 (9)	0.48629 (8)	0.41050 (7)	0.0179 (2)
O3	−0.02763 (9)	0.49810 (8)	0.17043 (8)	0.0192 (2)
N3	0.23046 (11)	0.79102 (10)	0.08260 (9)	0.0165 (2)
H3	0.2561	0.8585	0.0371	0.02*
N4	0.10361 (11)	0.46869 (9)	0.30785 (9)	0.0154 (2)
C22	0.19988 (12)	0.52244 (11)	0.32763 (10)	0.0147 (2)
C26	0.06391 (12)	0.78966 (12)	−0.03297 (10)	0.0157 (3)
C25	0.13700 (12)	0.73589 (11)	0.06384 (10)	0.0151 (3)
C21	0.21500 (12)	0.62799 (11)	0.22789 (10)	0.0152 (3)
C23	0.05479 (12)	0.53067 (11)	0.20333 (10)	0.0151 (3)
C24	0.12802 (12)	0.63298 (11)	0.15423 (10)	0.0150 (3)
C20	0.27846 (13)	0.72673 (12)	0.18161 (11)	0.0168 (3)
C31	0.00339 (14)	0.71767 (12)	−0.06663 (11)	0.0190 (3)
H31	0.0126	0.6338	−0.0286	0.023*
C32	0.05449 (13)	0.36364 (11)	0.38542 (10)	0.0157 (3)
C28	−0.02495 (14)	0.96323 (12)	−0.17831 (11)	0.0217 (3)
H28	−0.0347	1.0471	−0.2165	0.026*
C27	0.04938 (13)	0.91299 (12)	−0.08956 (11)	0.0187 (3)
H27	0.0905	0.9625	−0.0672	0.022*
C37	0.13017 (14)	0.25396 (12)	0.40797 (11)	0.0193 (3)
H37	0.2151	0.248	0.3739	0.023*
C36	0.08002 (15)	0.15257 (12)	0.48124 (12)	0.0236 (3)
H36	0.1313	0.0768	0.4983	0.028*
C30	−0.07021 (14)	0.76880 (13)	−0.15566 (12)	0.0224 (3)
H30	−0.1108	0.7196	−0.1787	0.027*
C34	−0.11889 (14)	0.27239 (13)	0.50622 (12)	0.0242 (3)
H34	−0.2041	0.2783	0.5397	0.029*
C33	−0.06943 (14)	0.37408 (12)	0.43446 (11)	0.0206 (3)
H33	−0.1198	0.4501	0.419	0.025*
C29	−0.08508 (14)	0.89119 (13)	−0.21134 (11)	0.0222 (3)
H29	−0.1362	0.9257	−0.2719	0.027*
C38	0.37168 (14)	0.77383 (12)	0.22422 (11)	0.0199 (3)
C35	−0.04424 (15)	0.16186 (13)	0.52922 (11)	0.0245 (3)
H35	−0.0787	0.0922	0.5782	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0173 (5)	0.0114 (5)	0.0137 (5)	−0.0008 (4)	−0.0019 (4)	−0.0026 (4)
N2	0.0183 (5)	0.0130 (5)	0.0143 (5)	−0.0014 (4)	−0.0012 (4)	−0.0026 (4)
F2	0.0338 (5)	0.0266 (5)	0.0431 (6)	−0.0007 (4)	−0.0007 (4)	−0.0242 (4)
F3	0.0475 (6)	0.0241 (5)	0.0342 (5)	0.0060 (4)	0.0236 (5)	0.0010 (4)
F1	0.0219 (5)	0.0552 (6)	0.0438 (6)	0.0131 (4)	−0.0119 (4)	−0.0324 (5)
O1	0.0212 (5)	0.0188 (5)	0.0164 (5)	−0.0041 (4)	0.0026 (4)	−0.0030 (4)
O2	0.0202 (5)	0.0185 (5)	0.0189 (5)	0.0020 (4)	0.0005 (4)	−0.0061 (4)
C12	0.0195 (6)	0.0172 (6)	0.0164 (6)	−0.0021 (5)	−0.0031 (5)	−0.0055 (5)
C1	0.0164 (6)	0.0139 (6)	0.0149 (6)	−0.0025 (5)	−0.0018 (5)	−0.0044 (5)
C6	0.0151 (6)	0.0142 (6)	0.0147 (6)	−0.0015 (5)	−0.0037 (5)	−0.0058 (5)
C3	0.0160 (6)	0.0132 (6)	0.0167 (6)	−0.0043 (5)	−0.0012 (5)	−0.0053 (5)
C2	0.0158 (6)	0.0143 (6)	0.0150 (6)	−0.0035 (5)	−0.0008 (5)	−0.0057 (5)
C7	0.0157 (6)	0.0171 (6)	0.0129 (6)	−0.0035 (5)	−0.0027 (5)	−0.0047 (5)
C4	0.0172 (6)	0.0140 (6)	0.0146 (6)	−0.0032 (5)	−0.0028 (5)	−0.0045 (5)
C5	0.0148 (6)	0.0141 (6)	0.0142 (6)	−0.0024 (5)	−0.0018 (5)	−0.0058 (5)
C13	0.0170 (6)	0.0139 (6)	0.0153 (6)	−0.0010 (5)	−0.0004 (5)	−0.0003 (5)
C8	0.0195 (6)	0.0171 (6)	0.0182 (6)	−0.0026 (5)	−0.0024 (5)	−0.0063 (5)
C9	0.0243 (7)	0.0197 (7)	0.0192 (7)	−0.0074 (5)	−0.0024 (5)	−0.0022 (5)
C14	0.0233 (7)	0.0179 (7)	0.0211 (7)	−0.0019 (5)	−0.0024 (5)	−0.0052 (6)
C11	0.0193 (7)	0.0268 (7)	0.0190 (7)	−0.0002 (5)	−0.0001 (5)	−0.0096 (6)
C18	0.0283 (8)	0.0243 (7)	0.0186 (7)	−0.0010 (6)	−0.0029 (6)	−0.0067 (6)
C10	0.0207 (7)	0.0296 (8)	0.0161 (7)	−0.0070 (6)	0.0021 (5)	−0.0044 (6)
C15	0.0309 (8)	0.0157 (7)	0.0307 (8)	0.0000 (6)	0.0024 (6)	−0.0042 (6)
C16	0.0350 (9)	0.0228 (8)	0.0229 (8)	0.0068 (6)	−0.0013 (6)	0.0047 (6)
C17	0.0379 (9)	0.0355 (9)	0.0163 (7)	0.0030 (7)	−0.0077 (6)	−0.0020 (6)
C19	0.0212 (7)	0.0153 (6)	0.0180 (6)	−0.0004 (5)	−0.0002 (5)	−0.0049 (5)
F4	0.0402 (6)	0.0568 (6)	0.0266 (5)	−0.0341 (5)	0.0090 (4)	−0.0172 (5)
F5	0.0337 (5)	0.0514 (6)	0.0435 (6)	−0.0149 (4)	0.0028 (4)	−0.0339 (5)
F6	0.0552 (7)	0.0263 (5)	0.0633 (7)	−0.0056 (5)	−0.0444 (6)	−0.0029 (5)
O4	0.0207 (5)	0.0152 (4)	0.0159 (5)	−0.0006 (4)	−0.0047 (4)	−0.0032 (4)
O3	0.0220 (5)	0.0173 (5)	0.0189 (5)	−0.0057 (4)	−0.0032 (4)	−0.0056 (4)
N3	0.0199 (6)	0.0138 (5)	0.0142 (5)	−0.0054 (4)	−0.0022 (4)	−0.0018 (4)
N4	0.0181 (5)	0.0121 (5)	0.0143 (5)	−0.0025 (4)	−0.0014 (4)	−0.0027 (4)
C22	0.0156 (6)	0.0127 (6)	0.0153 (6)	0.0001 (5)	0.0002 (5)	−0.0058 (5)
C26	0.0159 (6)	0.0173 (6)	0.0121 (6)	−0.0017 (5)	0.0002 (5)	−0.0041 (5)
C25	0.0164 (6)	0.0138 (6)	0.0155 (6)	−0.0021 (5)	0.0002 (5)	−0.0062 (5)
C21	0.0158 (6)	0.0142 (6)	0.0148 (6)	−0.0009 (5)	−0.0008 (5)	−0.0048 (5)
C23	0.0168 (6)	0.0123 (6)	0.0148 (6)	0.0004 (5)	−0.0001 (5)	−0.0049 (5)
C24	0.0158 (6)	0.0141 (6)	0.0145 (6)	−0.0010 (5)	−0.0010 (5)	−0.0053 (5)
C20	0.0184 (6)	0.0161 (6)	0.0148 (6)	−0.0026 (5)	−0.0017 (5)	−0.0040 (5)
C31	0.0239 (7)	0.0163 (6)	0.0165 (6)	−0.0037 (5)	−0.0021 (5)	−0.0049 (5)
C32	0.0211 (6)	0.0129 (6)	0.0123 (6)	−0.0042 (5)	−0.0024 (5)	−0.0027 (5)
C28	0.0240 (7)	0.0166 (6)	0.0201 (7)	−0.0017 (5)	−0.0042 (5)	−0.0014 (5)
C27	0.0205 (7)	0.0176 (6)	0.0178 (6)	−0.0038 (5)	−0.0019 (5)	−0.0057 (5)
C37	0.0240 (7)	0.0159 (6)	0.0177 (6)	−0.0008 (5)	−0.0018 (5)	−0.0064 (5)
C36	0.0369 (8)	0.0127 (6)	0.0201 (7)	−0.0017 (6)	−0.0052 (6)	−0.0044 (5)
C30	0.0255 (7)	0.0239 (7)	0.0203 (7)	−0.0059 (6)	−0.0048 (6)	−0.0087 (6)
C34	0.0221 (7)	0.0286 (8)	0.0188 (7)	−0.0081 (6)	0.0004 (5)	−0.0039 (6)
C33	0.0210 (7)	0.0176 (6)	0.0193 (7)	−0.0008 (5)	−0.0018 (5)	−0.0033 (5)
C29	0.0218 (7)	0.0252 (7)	0.0174 (7)	−0.0027 (6)	−0.0062 (5)	−0.0039 (6)
C38	0.0218 (7)	0.0193 (7)	0.0173 (7)	−0.0067 (5)	−0.0031 (5)	−0.0033 (5)
C35	0.0368 (8)	0.0197 (7)	0.0160 (7)	−0.0138 (6)	−0.0029 (6)	−0.0010 (5)

Geometric parameters (Å, º) top

N1—C1	1.3731 (16)	F4—C38	1.3269 (16)
N1—C6	1.3776 (16)	F5—C38	1.3444 (17)
N1—H1	0.8800	F6—C38	1.3190 (17)
N2—C3	1.4018 (17)	O4—C22	1.2170 (16)
N2—C4	1.4240 (16)	O3—C23	1.2040 (16)
N2—C13	1.4332 (16)	N3—C20	1.3723 (17)
F2—C19	1.3391 (16)	N3—C25	1.3761 (17)
F3—C19	1.3213 (16)	N3—H3	0.8800
F1—C19	1.3288 (17)	N4—C22	1.3954 (17)
O1—C3	1.2139 (16)	N4—C23	1.4324 (16)
O2—C4	1.2076 (16)	N4—C32	1.4366 (16)
C12—C11	1.3884 (19)	C22—C21	1.4769 (17)
C12—C7	1.4018 (18)	C26—C31	1.3964 (19)
C12—H12	0.9500	C26—C27	1.3985 (18)
C1—C2	1.3689 (18)	C26—C25	1.4654 (18)
C1—C19	1.4837 (18)	C25—C24	1.3827 (18)
C6—C5	1.3823 (18)	C21—C20	1.3704 (18)
C6—C7	1.4636 (18)	C21—C24	1.4083 (18)
C3—C2	1.4735 (18)	C23—C24	1.4670 (18)
C2—C5	1.4074 (18)	C20—C38	1.4835 (18)
C7—C8	1.3996 (18)	C31—C30	1.3867 (19)
C4—C5	1.4663 (17)	C31—H31	0.9500
C13—C18	1.386 (2)	C32—C37	1.3840 (18)
C13—C14	1.3873 (19)	C32—C33	1.3858 (19)
C8—C9	1.3858 (19)	C28—C27	1.3881 (19)
C8—H8	0.9500	C28—C29	1.389 (2)
C9—C10	1.389 (2)	C28—H28	0.9500
C9—H9	0.9500	C27—H27	0.9500
C14—C15	1.388 (2)	C37—C36	1.3917 (19)
C14—H14	0.9500	C37—H37	0.9500
C11—C10	1.390 (2)	C36—C35	1.382 (2)
C11—H11	0.9500	C36—H36	0.9500
C18—C17	1.391 (2)	C30—C29	1.387 (2)
C18—H18	0.9500	C30—H30	0.9500
C10—H10	0.9500	C34—C33	1.3847 (19)
C15—C16	1.384 (2)	C34—C35	1.387 (2)
C15—H15	0.9500	C34—H34	0.9500
C16—C17	1.382 (2)	C33—H33	0.9500
C16—H16	0.9500	C29—H29	0.9500
C17—H17	0.9500	C35—H35	0.9500

C1—N1—C6	110.75 (10)	C20—N3—C25	111.02 (11)
C1—N1—H1	124.6	C20—N3—H3	124.5
C6—N1—H1	124.6	C25—N3—H3	124.5
C3—N2—C4	112.92 (10)	C22—N4—C23	113.47 (10)
C3—N2—C13	124.26 (11)	C22—N4—C32	123.71 (11)
C4—N2—C13	122.80 (11)	C23—N4—C32	122.80 (11)
C11—C12—C7	120.19 (12)	O4—C22—N4	125.38 (12)
C11—C12—H12	119.9	O4—C22—C21	130.17 (12)
C7—C12—H12	119.9	N4—C22—C21	104.44 (11)
C2—C1—N1	107.49 (11)	C31—C26—C27	119.49 (12)
C2—C1—C19	131.11 (12)	C31—C26—C25	119.70 (12)
N1—C1—C19	121.27 (11)	C27—C26—C25	120.75 (12)
N1—C6—C5	105.48 (11)	N3—C25—C24	105.57 (11)
N1—C6—C7	123.03 (11)	N3—C25—C26	122.20 (11)
C5—C6—C7	131.18 (12)	C24—C25—C26	132.11 (12)
O1—C3—N2	125.03 (12)	C20—C21—C24	107.44 (11)
O1—C3—C2	130.37 (12)	C20—C21—C22	143.29 (12)
N2—C3—C2	104.56 (10)	C24—C21—C22	109.19 (11)
C1—C2—C5	107.14 (11)	O3—C23—N4	123.71 (12)
C1—C2—C3	142.97 (12)	O3—C23—C24	132.10 (12)
C5—C2—C3	109.22 (11)	N4—C23—C24	104.19 (10)
C8—C7—C12	119.19 (12)	C25—C24—C21	108.83 (11)
C8—C7—C6	121.21 (12)	C25—C24—C23	142.33 (12)
C12—C7—C6	119.47 (12)	C21—C24—C23	108.72 (11)
O2—C4—N2	123.74 (12)	C21—C20—N3	107.14 (11)
O2—C4—C5	131.42 (12)	C21—C20—C38	131.64 (12)
N2—C4—C5	104.84 (11)	N3—C20—C38	120.92 (11)
C6—C5—C2	109.10 (11)	C30—C31—C26	119.88 (12)
C6—C5—C4	142.06 (12)	C30—C31—H31	120.1
C2—C5—C4	108.36 (11)	C26—C31—H31	120.1
C18—C13—C14	121.11 (13)	C37—C32—C33	121.29 (12)
C18—C13—N2	119.90 (12)	C37—C32—N4	119.62 (12)
C14—C13—N2	118.98 (12)	C33—C32—N4	119.07 (12)
C9—C8—C7	120.18 (13)	C27—C28—C29	120.13 (13)
C9—C8—H8	119.9	C27—C28—H28	119.9
C7—C8—H8	119.9	C29—C28—H28	119.9
C8—C9—C10	120.40 (13)	C28—C27—C26	120.12 (13)
C8—C9—H9	119.8	C28—C27—H27	119.9
C10—C9—H9	119.8	C26—C27—H27	119.9
C13—C14—C15	119.34 (14)	C32—C37—C36	118.99 (13)
C13—C14—H14	120.3	C32—C37—H37	120.5
C15—C14—H14	120.3	C36—C37—H37	120.5
C12—C11—C10	120.19 (13)	C35—C36—C37	120.13 (13)
C12—C11—H11	119.9	C35—C36—H36	119.9
C10—C11—H11	119.9	C37—C36—H36	119.9
C13—C18—C17	118.80 (14)	C31—C30—C29	120.55 (13)
C13—C18—H18	120.6	C31—C30—H30	119.7
C17—C18—H18	120.6	C29—C30—H30	119.7
C9—C10—C11	119.85 (13)	C33—C34—C35	120.09 (14)
C9—C10—H10	120.1	C33—C34—H34	120.0
C11—C10—H10	120.1	C35—C34—H34	120.0
C16—C15—C14	120.06 (15)	C34—C33—C32	119.20 (13)
C16—C15—H15	120.0	C34—C33—H33	120.4
C14—C15—H15	120.0	C32—C33—H33	120.4
C17—C16—C15	120.17 (14)	C30—C29—C28	119.82 (13)
C17—C16—H16	119.9	C30—C29—H29	120.1
C15—C16—H16	119.9	C28—C29—H29	120.1
C16—C17—C18	120.51 (15)	F6—C38—F4	109.15 (12)
C16—C17—H17	119.7	F6—C38—F5	106.22 (12)
C18—C17—H17	119.7	F4—C38—F5	104.84 (11)
F3—C19—F1	108.45 (12)	F6—C38—C20	112.20 (11)
F3—C19—F2	106.94 (12)	F4—C38—C20	112.23 (11)
F1—C19—F2	105.21 (11)	F5—C38—C20	111.78 (11)
F3—C19—C1	111.26 (11)	C36—C35—C34	120.29 (13)
F1—C19—C1	113.09 (11)	C36—C35—H35	119.9
F2—C19—C1	111.52 (11)	C34—C35—H35	119.9

C6—N1—C1—C2	−0.33 (14)	C23—N4—C22—O4	179.89 (12)
C6—N1—C1—C19	175.96 (11)	C32—N4—C22—O4	1.8 (2)
C1—N1—C6—C5	1.50 (14)	C23—N4—C22—C21	−0.01 (14)
C1—N1—C6—C7	−172.82 (11)	C32—N4—C22—C21	−178.08 (11)
C4—N2—C3—O1	−175.96 (12)	C20—N3—C25—C24	−0.67 (15)
C13—N2—C3—O1	5.5 (2)	C20—N3—C25—C26	175.96 (12)
C4—N2—C3—C2	2.17 (14)	C31—C26—C25—N3	159.02 (12)
C13—N2—C3—C2	−176.41 (11)	C27—C26—C25—N3	−23.69 (19)
N1—C1—C2—C5	−0.97 (14)	C31—C26—C25—C24	−25.4 (2)
C19—C1—C2—C5	−176.76 (13)	C27—C26—C25—C24	151.93 (14)
N1—C1—C2—C3	167.80 (16)	O4—C22—C21—C20	−3.9 (3)
C19—C1—C2—C3	−8.0 (3)	N4—C22—C21—C20	176.03 (18)
O1—C3—C2—C1	6.3 (3)	O4—C22—C21—C24	−179.59 (13)
N2—C3—C2—C1	−171.73 (17)	N4—C22—C21—C24	0.30 (14)
O1—C3—C2—C5	174.89 (13)	C22—N4—C23—O3	179.29 (12)
N2—C3—C2—C5	−3.10 (14)	C32—N4—C23—O3	−2.62 (19)
C11—C12—C7—C8	0.25 (19)	C22—N4—C23—C24	−0.26 (14)
C11—C12—C7—C6	−175.56 (12)	C32—N4—C23—C24	177.83 (11)
N1—C6—C7—C8	20.70 (19)	N3—C25—C24—C21	1.02 (14)
C5—C6—C7—C8	−152.02 (14)	C26—C25—C24—C21	−175.14 (13)
N1—C6—C7—C12	−163.58 (12)	N3—C25—C24—C23	176.03 (16)
C5—C6—C7—C12	23.7 (2)	C26—C25—C24—C23	−0.1 (3)
C3—N2—C4—O2	179.17 (12)	C20—C21—C24—C25	−1.01 (15)
C13—N2—C4—O2	−2.2 (2)	C22—C21—C24—C25	176.32 (11)
C3—N2—C4—C5	−0.48 (14)	C20—C21—C24—C23	−177.80 (11)
C13—N2—C4—C5	178.13 (11)	C22—C21—C24—C23	−0.47 (14)
N1—C6—C5—C2	−2.08 (14)	O3—C23—C24—C25	5.9 (3)
C7—C6—C5—C2	171.59 (13)	N4—C23—C24—C25	−174.58 (17)
N1—C6—C5—C4	−172.55 (16)	O3—C23—C24—C21	−179.05 (14)
C7—C6—C5—C4	1.1 (3)	N4—C23—C24—C21	0.44 (13)
C1—C2—C5—C6	1.93 (15)	C24—C21—C20—N3	0.58 (15)
C3—C2—C5—C6	−170.94 (11)	C22—C21—C20—N3	−175.20 (17)
C1—C2—C5—C4	175.77 (11)	C24—C21—C20—C38	174.17 (14)
C3—C2—C5—C4	2.91 (14)	C22—C21—C20—C38	−1.6 (3)
O2—C4—C5—C6	−10.6 (3)	C25—N3—C20—C21	0.06 (15)
N2—C4—C5—C6	168.98 (16)	C25—N3—C20—C38	−174.36 (12)
O2—C4—C5—C2	178.85 (14)	C27—C26—C31—C30	0.1 (2)
N2—C4—C5—C2	−1.54 (13)	C25—C26—C31—C30	177.41 (13)
C3—N2—C13—C18	−63.64 (18)	C22—N4—C32—C37	−73.65 (17)
C4—N2—C13—C18	117.91 (15)	C23—N4—C32—C37	108.45 (14)
C3—N2—C13—C14	117.16 (15)	C22—N4—C32—C33	107.80 (15)
C4—N2—C13—C14	−61.29 (17)	C23—N4—C32—C33	−70.09 (17)
C12—C7—C8—C9	−0.22 (19)	C29—C28—C27—C26	−0.1 (2)
C6—C7—C8—C9	175.51 (12)	C31—C26—C27—C28	0.2 (2)
C7—C8—C9—C10	−0.3 (2)	C25—C26—C27—C28	−177.12 (12)
C18—C13—C14—C15	0.3 (2)	C33—C32—C37—C36	0.1 (2)
N2—C13—C14—C15	179.44 (13)	N4—C32—C37—C36	−178.38 (12)
C7—C12—C11—C10	0.2 (2)	C32—C37—C36—C35	0.9 (2)
C14—C13—C18—C17	−0.5 (2)	C26—C31—C30—C29	−0.4 (2)
N2—C13—C18—C17	−179.69 (13)	C35—C34—C33—C32	0.7 (2)
C12—C11—C10—C9	−0.7 (2)	C37—C32—C33—C34	−0.9 (2)
C8—C9—C10—C11	0.8 (2)	N4—C32—C33—C34	177.59 (12)
C13—C14—C15—C16	0.0 (2)	C31—C30—C29—C28	0.5 (2)
C14—C15—C16—C17	0.1 (2)	C27—C28—C29—C30	−0.3 (2)
C15—C16—C17—C18	−0.4 (3)	C21—C20—C38—F6	32.2 (2)
C13—C18—C17—C16	0.6 (2)	N3—C20—C38—F6	−154.97 (13)
C2—C1—C19—F3	−7.4 (2)	C21—C20—C38—F4	155.50 (14)
N1—C1—C19—F3	177.30 (12)	N3—C20—C38—F4	−31.64 (18)
C2—C1—C19—F1	−129.75 (15)	C21—C20—C38—F5	−87.03 (18)
N1—C1—C19—F1	54.95 (17)	N3—C20—C38—F5	85.83 (15)
C2—C1—C19—F2	111.91 (16)	C37—C36—C35—C34	−1.2 (2)
N1—C1—C19—F2	−63.39 (16)	C33—C34—C35—C36	0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	2.01	2.8395 (14)	156
N1—H1···O4	0.88	2.00	2.8757 (14)	173

Symmetry code: (i) x, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₁F₃N₂O₂
M_r	356.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.4730 (4), 12.2394 (5), 13.4379 (5)
α, β, γ (°)	67.542 (2), 82.511 (2), 80.294 (2)
V (Å³)	1564.98 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.86, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	32220, 6660, 5882
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.089, 0.98
No. of reflections	6660
No. of parameters	469
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008) and OLEX2 (Dolomanov et al., 2009)., publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	2.01	2.8395 (14)	155.7
N1—H1···O4	0.88	2.00	2.8757 (14)	173.4

Symmetry code: (i) x, y+1, z−1.

Acknowledgements

The Bruker Kappa APEXII DUO was purchased with funding from NSF grant CHE-0741837.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Malinka, W., Kaczmarz, M., Redzicka, A., Filipek, B. & Sapa, J. (2005). Farmaco, 60, 15-22. CrossRef PubMed CAS Google Scholar
Malinka, W., Sieklucka-Dziuba, M., Rajtar, G., Rubaj, A. & Kleinrok, Z. (1999). Farmaco, 54, 390–401. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, Y.-M., Lv, P.-C., Chen, W., Liu, P.-G., Zhang, M.-Z. & Zhu, H.-L. (2010). Eur. J. Med. Chem. 45, 3184–3190. Web of Science CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, C., Zhang, Y., Zhang, S., Li, H. & Wang, W. (2011). Chem. Commun. 47, 1036–1038. Web of Science CrossRef CAS Google Scholar

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Volume 68| Part 2| February 2012| Pages o496-o497

doi:10.1107/S1600536812001675

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

2,4-Di­phenyl-6-tri­fluoro­methyl-2,3-di­hydro-1H,5H-pyrrolo­[3,4-c]pyrrole-1,3-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,4-Diphenyl-6-trifluoromethyl-2,3-dihydro-1H,5H-pyrrolo[3,4-c]pyrrole-1,3-dione