Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]iso­quinoline-11-carboxyl­ate–tri­fluoro­acetic acid (1/1)

Stibrany, R.T.; Potenza, J.A.

doi:10.1107/S1600536813013834

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o977-o978

doi:10.1107/S1600536813013834

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Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]isoquinoline-11-carboxylate–trifluoroacetic acid (1/1)

Robert T. Stibrany ^a ^* and Joseph A. Potenza ^a

^aDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA
^*Correspondence e-mail: dzsquared@aol.com

(Received 27 March 2013; accepted 20 May 2013; online 31 May 2013)

The structure of the title trifluoroacetic acid adduct, C₁₇H₁₂N₂O₃·C₂HF₃O₂, contains a trifluoroacetic acid molecule hydrogen bonded to the imine N atom of the imidazole ring of a nearly planar four-fused-ring system (r.m.s. deviatiation = 0.013 Å). The carboxylic acid group of the triflouroacetic acid molecule is twisted with respect to the mean plane of the four-fused-ring sytem by 75.9 (2)°. A short intramolecular C—H⋯O hydrogen bond occurs. In the crystal, the adduct molecules are arranged into stacks along the b axis via π–π interactions between imidazole rings and between imidazole and one of the benzene rings [centroid–centroid distances 3.352 (2) and 3.485 (2) Å, respectively]. Molecules are linked via C—H⋯O hydrogen bonds, forming an alternating polymeric head-to-head/tail-to-tail stepped chain approximately along the a-axis direction and tilted on an axis bisecting the b and c axes.

Related literature

For ¹⁹F NMR studies of related compounds, see: Stibrany (2003 ). For polymerization studies, see: Stibrany et al. (2003 ). For their use as agents to study electron transfer, see: Knapp et al. (1990 ). For related structures, see: Baugh et al. (2006 ); Stibrany (2003); Stibrany et al. (2002 , 2004 ); Stibrany & Potenza (2008 , 2009 ); Gorun et al. (1996 ).

Experimental

Crystal data

C₁₇H₁₂N₂O₃·C₂HF₃O₂
M_r = 406.31
Triclinic, $[P \overline 1]$
a = 7.642 (3) Å
b = 8.111 (4) Å
c = 14.043 (6) Å
α = 97.539 (8)°
β = 98.055 (8)°
γ = 92.695 (8)°
V = 852.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 100 K
0.48 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ; Blessing, 1995 ) T_min = 0.711, T_max = 1.00
7689 measured reflections
3380 independent reflections
2642 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.140
S = 1.00
3380 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯O11	0.93	2.15	2.981 (3)	148
O2—H2O⋯N13	1.03 (3)	1.58 (3)	2.597 (2)	170 (3)
C13—H13⋯O30ⁱ	0.93	2.28	3.143 (3)	154
C23—H23⋯O11ⁱⁱ	0.93	2.46	3.320 (3)	155
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013834/gk2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013834/gk2567Isup2.hkl

checkCIF report

Comment top

The title compound, Fig. 1, was isolated as part of our long-term interest in the chemistry of bis (imidazoles), bis(benzimidazoles), and their complexes with metal ions. These species have demonstrated their usefulness as proton sponges (Stibrany et al., 2002), geometrically constraining ligands (Stibrany et al., 2004), agents to study electron transfer (Knapp et al., 1990), polymerization catalysts (Stibrany et al., 2003; Baugh et al., 2006), ¹⁹F NMR polymerization catalyst probes (Stibrany, 2003), and in the formation of metal-organic copolymers (Stibrany & Potenza, 2008). Previously, we have shown that 1-methylbenzimidazole can be used in the synthesis of bis(benzimidazole)ketones, which were found to be useful ligands for the chelation of metals (Gorun et al., 1996).

Our investigation into the synthesis of acenapthoimidazoles as building blocks for higher dentate ligands led us to attempt a similar method of preparation as for phenanthroimidazoles (Stibrany & Potenza, 2009). The title compound was isolated by chromatography as a side product of that preparation. The trifluoroacetic acid adduct [C₁₈H₁₂N₂O₃][C₂HF₃O₂] contains trifluoroacetic acid molecule, hydrogen bonded to the imine nitrogen of the imidazole ring of a nearly-planar, four-fused-ring system (r.m.s. deviatiation = 0.013 Å). A carbonyl-centroid interaction is formed by C41-O11 to the centroid formed by C20, C25/C29 (-x+1, -y, -z+1) with a O11-Cg distance of 3.567 (2) Å and a C41-O11···Cg angle of 78.0 (1)°. In the space group P1 , the adduct molecules are centrosymmetrically disposed about the origin, and form π-π dimers through the imidazole rings along the b cell direction Fig 2. The first Cg-Cg interaction is the imidazole ring (N11, N13, C11/C13) paired to a symmetry related imidazole (-x+1, -y+1, -z+1) at a distance of 3.352 (2) Å. A second Cg-Cg interaction is formed by the imidazole ring and the centroid C21/C26 (-x+1, -y, 1-z) at a distance of 3.485 (2) Å. There are three short intermolecular hydrogen bonds and one short intramolecular hydrogen bond found in the structure and are listed in the hydrogen-bond Table 1. No additional electron density was located near N13 in the difference Fourier maps, likely due to the electron-withdrawing effect of the adjacent ethyl ester group.

Related literature top

For ¹⁹F NMR studies of related compounds, see: Stibrany (2003). For polymerization studies, see: Stibrany et al. (2003). For their use as agents to study electron transfer, see: Knapp et al. (1990). For related structures, see: Baugh et al. (2006); Stibrany (2003); Stibrany et al. (2002, 2004); Stibrany & Potenza (2008, 2009); Gorun et al. (1996).

Experimental top

The title compound was isolated as a minor side product in the condensation of acenaphthaquinone in place of phenanthroquinone (Stibrany & Potenza, 2009). A small yellow–orange band was isolated by chromatography on silica gel using ethyl acetate as the eluent. Two X-ray quality crystals were obtained by slow evaporation of a 10:1 v/v methanol/trifluoroacetic acid solution of the title compound.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are shown at the 40% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Packing of the π-π stacked imidazole dimers approximately along the b axis in the unit cell viewed approximately down the a axis.

Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]isoquinoline-11-carboxylate–trifluoroacetic acid (1/1) top

Crystal data top

C₁₇H₁₂N₂O₃·C₂HF₃O₂	Z = 2
M_r = 406.31	F(000) = 416
Triclinic, P1	D_x = 1.583 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.642 (3) Å	Cell parameters from 800 reflections
b = 8.111 (4) Å	θ = 2.5–26.0°
c = 14.043 (6) Å	µ = 0.14 mm⁻¹
α = 97.539 (8)°	T = 100 K
β = 98.055 (8)°	Spike, yellow
γ = 92.695 (8)°	0.48 × 0.10 × 0.07 mm
V = 852.6 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	2642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	h = −9→9
T_min = 0.711, T_max = 1.00	k = −10→10
7689 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0934P)² + 0.124P] where P = (F_o² + 2F_c²)/3
3380 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₁₂N₂O₃·C₂HF₃O₂	γ = 92.695 (8)°
M_r = 406.31	V = 852.6 (6) Å³
Triclinic, P1	Z = 2
a = 7.642 (3) Å	Mo Kα radiation
b = 8.111 (4) Å	µ = 0.14 mm⁻¹
c = 14.043 (6) Å	T = 100 K
α = 97.539 (8)°	0.48 × 0.10 × 0.07 mm
β = 98.055 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3380 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	2642 reflections with I > 2σ(I)
T_min = 0.711, T_max = 1.00	R_int = 0.032
7689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.42 e Å⁻³
3380 reflections	Δρ_min = −0.28 e Å⁻³
267 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
F1	0.25760 (19)	0.12397 (17)	0.05463 (9)	0.0435 (4)
F2	0.0782 (2)	0.27375 (17)	−0.01973 (9)	0.0460 (4)
F3	−0.0070 (2)	0.13711 (19)	0.08785 (10)	0.0550 (5)
O1	0.1872 (2)	0.51438 (18)	0.12697 (11)	0.0390 (4)
O2	0.2409 (2)	0.32127 (17)	0.22686 (10)	0.0300 (4)
O11	0.79755 (19)	0.70261 (18)	0.38002 (10)	0.0310 (4)
O12	0.60779 (18)	0.52898 (16)	0.27167 (9)	0.0242 (3)
O30	0.08434 (17)	0.69206 (16)	0.60128 (9)	0.0250 (3)
N11	0.3148 (2)	0.69116 (18)	0.51474 (11)	0.0185 (3)
N13	0.3464 (2)	0.54546 (18)	0.37627 (11)	0.0201 (4)
C1	0.1900 (3)	0.3743 (2)	0.14513 (13)	0.0242 (4)
C2	0.1289 (3)	0.2258 (3)	0.06570 (14)	0.0276 (5)
C11	0.4856 (2)	0.7380 (2)	0.49858 (13)	0.0183 (4)
C12	0.5023 (2)	0.6433 (2)	0.41081 (12)	0.0189 (4)
C13	0.2372 (2)	0.5763 (2)	0.43870 (12)	0.0199 (4)
H13	0.1230	0.5272	0.4325	0.024*
C20	0.5334 (3)	1.1120 (2)	0.80732 (13)	0.0260 (5)
H20	0.5971	1.1923	0.8543	0.031*
C21	0.5911 (2)	0.8628 (2)	0.57107 (12)	0.0185 (4)
C22	0.7608 (2)	0.9217 (2)	0.56293 (13)	0.0217 (4)
H22	0.8127	0.8794	0.5096	0.026*
C23	0.8557 (3)	1.0438 (2)	0.63361 (14)	0.0248 (4)
H23	0.9689	1.0822	0.6262	0.030*
C24	0.7837 (3)	1.1071 (2)	0.71340 (14)	0.0247 (4)
H24	0.8483	1.1877	0.7599	0.030*
C25	0.6110 (3)	1.0504 (2)	0.72550 (13)	0.0224 (4)
C26	0.5131 (2)	0.9275 (2)	0.65349 (13)	0.0193 (4)
C27	0.3396 (3)	0.8738 (2)	0.66789 (13)	0.0205 (4)
C28	0.2685 (3)	0.9367 (2)	0.74925 (13)	0.0241 (4)
H28	0.1553	0.8993	0.7573	0.029*
C29	0.3665 (3)	1.0565 (2)	0.81947 (14)	0.0281 (5)
H29	0.3188	1.0986	0.8744	0.034*
C30	0.2317 (2)	0.7487 (2)	0.59630 (13)	0.0191 (4)
C41	0.6521 (2)	0.6321 (2)	0.35499 (13)	0.0206 (4)
C42	0.7451 (3)	0.5121 (3)	0.20891 (14)	0.0274 (5)
H42A	0.8381	0.4469	0.2358	0.033*
H42B	0.7970	0.6210	0.2027	0.033*
C43	0.6566 (3)	0.4257 (3)	0.11143 (14)	0.0346 (5)
H43A	0.6112	0.3161	0.1181	0.052*
H43B	0.7413	0.4172	0.0668	0.052*
H43C	0.5610	0.4886	0.0872	0.052*
H2O	0.284 (4)	0.419 (4)	0.281 (2)	0.061 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0536 (9)	0.0426 (8)	0.0288 (7)	0.0170 (6)	−0.0016 (6)	−0.0117 (6)
F2	0.0704 (10)	0.0429 (8)	0.0192 (6)	0.0082 (7)	−0.0094 (6)	−0.0009 (5)
F3	0.0627 (10)	0.0589 (9)	0.0352 (8)	−0.0337 (8)	0.0193 (7)	−0.0232 (7)
O1	0.0595 (11)	0.0267 (8)	0.0269 (8)	0.0030 (7)	−0.0062 (7)	0.0029 (6)
O2	0.0476 (9)	0.0231 (7)	0.0164 (7)	−0.0031 (6)	−0.0007 (6)	−0.0004 (6)
O11	0.0297 (8)	0.0378 (8)	0.0236 (7)	−0.0072 (6)	0.0089 (6)	−0.0049 (6)
O12	0.0290 (7)	0.0273 (7)	0.0157 (6)	0.0000 (6)	0.0065 (5)	−0.0020 (5)
O30	0.0243 (7)	0.0270 (7)	0.0231 (7)	−0.0040 (6)	0.0063 (5)	0.0000 (5)
N11	0.0216 (8)	0.0182 (8)	0.0153 (7)	−0.0011 (6)	0.0027 (6)	0.0016 (6)
N13	0.0258 (8)	0.0189 (8)	0.0149 (7)	−0.0004 (6)	0.0013 (6)	0.0025 (6)
C1	0.0257 (10)	0.0276 (11)	0.0189 (9)	0.0026 (8)	0.0027 (7)	0.0021 (8)
C2	0.0310 (11)	0.0327 (11)	0.0188 (10)	0.0023 (9)	0.0038 (8)	0.0023 (8)
C11	0.0205 (9)	0.0189 (9)	0.0162 (9)	0.0016 (7)	0.0023 (7)	0.0049 (7)
C12	0.0228 (9)	0.0183 (9)	0.0149 (8)	0.0000 (7)	0.0002 (7)	0.0027 (7)
C13	0.0229 (9)	0.0201 (9)	0.0156 (9)	−0.0016 (7)	0.0002 (7)	0.0029 (7)
C20	0.0382 (12)	0.0202 (10)	0.0166 (9)	0.0002 (8)	−0.0010 (8)	−0.0023 (7)
C21	0.0239 (9)	0.0167 (9)	0.0140 (8)	0.0004 (7)	−0.0002 (7)	0.0027 (7)
C22	0.0254 (10)	0.0217 (9)	0.0179 (9)	0.0017 (7)	0.0024 (7)	0.0036 (7)
C23	0.0237 (10)	0.0239 (10)	0.0259 (10)	−0.0004 (8)	−0.0004 (8)	0.0054 (8)
C24	0.0291 (11)	0.0193 (9)	0.0225 (10)	−0.0035 (8)	−0.0042 (8)	0.0009 (7)
C25	0.0306 (10)	0.0183 (9)	0.0173 (9)	0.0024 (8)	−0.0009 (8)	0.0027 (7)
C26	0.0249 (10)	0.0167 (9)	0.0160 (9)	0.0012 (7)	0.0010 (7)	0.0038 (7)
C27	0.0272 (10)	0.0191 (9)	0.0156 (9)	0.0027 (8)	0.0023 (7)	0.0041 (7)
C28	0.0291 (11)	0.0244 (10)	0.0201 (9)	0.0025 (8)	0.0064 (8)	0.0045 (7)
C29	0.0398 (12)	0.0272 (11)	0.0166 (9)	0.0052 (9)	0.0053 (8)	−0.0016 (8)
C30	0.0222 (10)	0.0209 (9)	0.0153 (8)	0.0029 (7)	0.0046 (7)	0.0039 (7)
C41	0.0277 (10)	0.0185 (9)	0.0158 (9)	0.0001 (8)	0.0036 (7)	0.0027 (7)
C42	0.0315 (11)	0.0321 (11)	0.0209 (10)	0.0041 (9)	0.0109 (8)	0.0038 (8)
C43	0.0412 (13)	0.0452 (13)	0.0183 (10)	0.0076 (10)	0.0086 (9)	0.0013 (9)

Geometric parameters (Å, º) top

F1—C2	1.326 (3)	C20—H20	0.9300
F2—C2	1.322 (2)	C21—C22	1.386 (3)
F3—C2	1.332 (2)	C21—C26	1.426 (3)
O1—C1	1.197 (2)	C22—C23	1.402 (3)
O2—C1	1.294 (2)	C22—H22	0.9300
O2—H2O	1.03 (3)	C23—C24	1.368 (3)
O11—C41	1.210 (2)	C23—H23	0.9300
O12—C41	1.338 (2)	C24—C25	1.418 (3)
O12—C42	1.462 (2)	C24—H24	0.9300
O30—C30	1.211 (2)	C25—C26	1.425 (3)
N11—C13	1.368 (2)	C26—C27	1.425 (3)
N11—C11	1.399 (2)	C27—C28	1.381 (3)
N11—C30	1.423 (2)	C27—C30	1.463 (3)
N13—C13	1.302 (3)	C28—C29	1.397 (3)
N13—C12	1.390 (2)	C28—H28	0.9300
C1—C2	1.537 (3)	C29—H29	0.9300
C11—C12	1.390 (3)	C42—C43	1.506 (3)
C11—C21	1.461 (2)	C42—H42A	0.9700
C12—C41	1.475 (3)	C42—H42B	0.9700
C13—H13	0.9300	C43—H43A	0.9600
C20—C29	1.373 (3)	C43—H43B	0.9600
C20—C25	1.410 (3)	C43—H43C	0.9600

C1—O2—H2O	111.3 (16)	C23—C24—C25	120.26 (17)
C41—O12—C42	115.50 (15)	C23—C24—H24	119.9
C13—N11—C11	108.78 (15)	C25—C24—H24	119.9
C13—N11—C30	124.09 (15)	C20—C25—C24	121.70 (17)
C11—N11—C30	127.13 (15)	C20—C25—C26	118.99 (18)
C13—N13—C12	107.70 (15)	C24—C25—C26	119.30 (18)
O1—C1—O2	129.19 (18)	C25—C26—C27	117.75 (17)
O1—C1—C2	120.89 (18)	C25—C26—C21	119.44 (17)
O2—C1—C2	109.92 (17)	C27—C26—C21	122.81 (16)
F2—C2—F1	107.05 (17)	C28—C27—C26	121.52 (17)
F2—C2—F3	107.57 (17)	C28—C27—C30	118.02 (18)
F1—C2—F3	107.45 (18)	C26—C27—C30	120.46 (17)
F2—C2—C1	112.15 (17)	C27—C28—C29	120.05 (19)
F1—C2—C1	111.43 (16)	C27—C28—H28	120.0
F3—C2—C1	110.95 (16)	C29—C28—H28	120.0
C12—C11—N11	103.93 (15)	C20—C29—C28	119.86 (19)
C12—C11—C21	138.42 (17)	C20—C29—H29	120.1
N11—C11—C21	117.65 (16)	C28—C29—H29	120.1
C11—C12—N13	109.43 (16)	O30—C30—N11	119.32 (16)
C11—C12—C41	130.92 (17)	O30—C30—C27	126.38 (17)
N13—C12—C41	119.64 (16)	N11—C30—C27	114.30 (16)
N13—C13—N11	110.16 (16)	O11—C41—O12	123.27 (17)
N13—C13—H13	124.9	O11—C41—C12	125.94 (17)
N11—C13—H13	124.9	O12—C41—C12	110.78 (16)
C29—C20—C25	121.82 (17)	O12—C42—C43	106.77 (16)
C29—C20—H20	119.1	O12—C42—H42A	110.4
C25—C20—H20	119.1	C43—C42—H42A	110.4
C22—C21—C26	119.02 (16)	O12—C42—H42B	110.4
C22—C21—C11	123.35 (17)	C43—C42—H42B	110.4
C26—C21—C11	117.63 (17)	H42A—C42—H42B	108.6
C21—C22—C23	121.24 (18)	C42—C43—H43A	109.5
C21—C22—H22	119.4	C42—C43—H43B	109.5
C23—C22—H22	119.4	H43A—C43—H43B	109.5
C24—C23—C22	120.73 (19)	C42—C43—H43C	109.5
C24—C23—H23	119.6	H43A—C43—H43C	109.5
C22—C23—H23	119.6	H43B—C43—H43C	109.5

O1—C1—C2—F2	0.6 (3)	C20—C25—C26—C27	0.5 (3)
O2—C1—C2—F2	−178.97 (17)	C24—C25—C26—C27	−179.78 (16)
O1—C1—C2—F1	120.6 (2)	C20—C25—C26—C21	−179.23 (16)
O2—C1—C2—F1	−59.0 (2)	C24—C25—C26—C21	0.5 (3)
O1—C1—C2—F3	−119.7 (2)	C22—C21—C26—C25	−0.1 (3)
O2—C1—C2—F3	60.7 (2)	C11—C21—C26—C25	−179.51 (16)
C13—N11—C11—C12	−0.7 (2)	C22—C21—C26—C27	−179.83 (16)
C30—N11—C11—C12	178.48 (16)	C11—C21—C26—C27	0.8 (3)
C13—N11—C11—C21	179.02 (15)	C25—C26—C27—C28	−0.7 (3)
C30—N11—C11—C21	−1.8 (3)	C21—C26—C27—C28	178.95 (17)
N11—C11—C12—N13	0.52 (19)	C25—C26—C27—C30	179.58 (16)
C21—C11—C12—N13	−179.2 (2)	C21—C26—C27—C30	−0.7 (3)
N11—C11—C12—C41	−178.54 (17)	C26—C27—C28—C29	0.4 (3)
C21—C11—C12—C41	1.8 (4)	C30—C27—C28—C29	−179.91 (17)
C13—N13—C12—C11	−0.1 (2)	C25—C20—C29—C28	−0.5 (3)
C13—N13—C12—C41	179.07 (16)	C27—C28—C29—C20	0.2 (3)
C12—N13—C13—N11	−0.4 (2)	C13—N11—C30—O30	1.5 (3)
C11—N11—C13—N13	0.7 (2)	C11—N11—C30—O30	−177.63 (16)
C30—N11—C13—N13	−178.53 (15)	C13—N11—C30—C27	−179.09 (15)
C12—C11—C21—C22	0.7 (3)	C11—N11—C30—C27	1.8 (3)
N11—C11—C21—C22	−178.98 (16)	C28—C27—C30—O30	−0.8 (3)
C12—C11—C21—C26	180.0 (2)	C26—C27—C30—O30	178.88 (17)
N11—C11—C21—C26	0.4 (2)	C28—C27—C30—N11	179.81 (15)
C26—C21—C22—C23	−0.5 (3)	C26—C27—C30—N11	−0.5 (2)
C11—C21—C22—C23	178.86 (16)	C42—O12—C41—O11	−2.9 (3)
C21—C22—C23—C24	0.7 (3)	C42—O12—C41—C12	178.27 (15)
C22—C23—C24—C25	−0.3 (3)	C11—C12—C41—O11	3.7 (3)
C29—C20—C25—C24	−179.62 (18)	N13—C12—C41—O11	−175.24 (18)
C29—C20—C25—C26	0.1 (3)	C11—C12—C41—O12	−177.52 (18)
C23—C24—C25—C20	179.44 (17)	N13—C12—C41—O12	3.5 (2)
C23—C24—C25—C26	−0.3 (3)	C41—O12—C42—C43	−166.99 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O11	0.93	2.15	2.981 (3)	148
O2—H2O···N13	1.03 (3)	1.58 (3)	2.597 (2)	170 (3)
C13—H13···O30ⁱ	0.93	2.28	3.143 (3)	154
C23—H23···O11ⁱⁱ	0.93	2.46	3.320 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₂O₃·C₂HF₃O₂
M_r	406.31
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.642 (3), 8.111 (4), 14.043 (6)
α, β, γ (°)	97.539 (8), 98.055 (8), 92.695 (8)
V (Å³)	852.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.48 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000; Blessing, 1995)
T_min, T_max	0.711, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	7689, 3380, 2642
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.140, 1.00
No. of reflections	3380
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.28

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O11	0.93	2.15	2.981 (3)	148
O2—H2O···N13	1.03 (3)	1.58 (3)	2.597 (2)	170 (3)
C13—H13···O30ⁱ	0.93	2.28	3.143 (3)	154
C23—H23···O11ⁱⁱ	0.93	2.46	3.320 (3)	155

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

References

Baugh, L. S., Sissano, J. A., Kacker, S., Berluche, E., Stibrany, R. T., Schulz, D. N. & Rucker, S. P. (2006). J. Polym. Sci. Part A Polym. Chem. 44, 1817–1840. Web of Science CSD CrossRef CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gorun, S. M., Stibrany, R. T., Katritzky, A. R., Slawinski, J. J., Faid-Allah, H. & Brunner, F. (1996). Inorg. Chem. 35, 3–4. CSD CrossRef PubMed CAS Web of Science Google Scholar
Knapp, S., Keenan, T. P., Zhang, X., Fikar, R., Potenza, J. A. & Schugar, H. J. (1990). J. Am. Chem. Soc. 112, 3452–3464. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure ¹⁹F NMR Catalyst Probe, ACS Symp. Series 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210–221. Washington, DC: ACS Press. Google Scholar
Stibrany, R. T., Lobanov, M. V., Schugar, H. J. & Potenza, J. A. (2004). Inorg. Chem. 43, 1472–1480. Web of Science CSD CrossRef PubMed CAS Google Scholar
Stibrany, R. T. & Potenza, J. A. (2008). Acta Cryst. C64, m213–m216. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Stibrany, R. T. & Potenza, J. A. (2009). Acta Cryst. C65, o406–o409. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142–o1144. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Stibrany, R. T., Schulz, D. N., Kacker, S., Patil, A. O., Baugh, L. S., Rucker, S. P., Zushma, S., Berluche, E. & Sissano, J. A. (2003). Macromolecules, 36, 8584–8586. Web of Science CSD CrossRef CAS Google Scholar

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Volume 69| Part 6| June 2013| Pages o977-o978

doi:10.1107/S1600536813013834

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

Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]iso­quinoline-11-carboxyl­ate–tri­fluoro­acetic acid (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]isoquinoline-11-carboxylate–trifluoroacetic acid (1/1)