Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]iso-quinoline-11-carboxyl-ate-tri-fluoro-acetic acid (1/1).

The structure of the title tri-fluoro-acetic acid adduct, C17H12N2O3·C2HF3O2, contains a tri-fluoro-acetic acid mol-ecule 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 carb-oxy-lic acid group of the triflouro-acetic acid mol-ecule is twisted with respect to the mean plane of the four-fused-ring sytem by 75.9 (2)°. A short intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, the adduct mol-ecules are arranged into stacks along the b axis via π-π inter-actions 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 = 406.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.140

S = 1.00

3380 reflections

267 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013834/gk2567sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12N2O3·C2HF3O2	Z = 2
Mr = 406.31	F(000) = 416
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0934P)2 + 0.124P] where P = (Fo2 + 2Fc2)/3
3380 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .