9,10-Dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one

Chen, Y.M.; Shi, J.C.

doi:10.1107/S1600536812022921

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1886

doi:10.1107/S1600536812022921

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9,10-Dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one

Yu Mei Chen ^a ^* and Jian Chao Shi ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo, Henan 454000, People's Republic of China
^*Correspondence e-mail: chenyumei@hpu.edu.cn

(Received 24 April 2012; accepted 19 May 2012; online 26 May 2012)

In the title compound, C₁₄H₁₀N₂O, all non-H atoms are essentially coplanar (r.m.s. deviation = 0.013 Å). The crystal structure is stabilized by π–π stacking interactions [centroid–centroid distance = 3.506 (3) Å].

Related literature

For the use of rigid ligands in the formation of metal-organic coordination polymers, see: Chen et al. (2006 ); Yang et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.4949 (2) Å
b = 14.9891 (9) Å
c = 15.1357 (8) Å
V = 1019.76 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.995
8736 measured reflections
1837 independent reflections
1207 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.202
S = 1.01
1837 reflections
154 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022921/bx2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022921/bx2409Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₄H₁₀N₂O, (I) can be used as a rigid ligand to form metal-organic coordination polymers, such as [Ag(C₁₄H₁₀N₂O)(NO₃)]_n, [Ag(C₁₄H₁₀N₂O)₂(NO₃)]_n, [Ag(C₁₄H₁₀N₂O)₂ (BF₄)]_n(Yang et al., 2009) and [Cu₂(CH₃COO)₄(C₁₄H₁₀N₂O)₂]_n (Chen et al., 2006). However, the crystal structure of 9,10-dihydro-7H-benzo[de]imidazo[2,1-a]-isoquinolin-7-one have not been reported so far. We report herein the synthesize and the crystal structure of (I). In the title molecule , C₁₄H₁₀N₂O, all non-H atoms are essentially coplanar (r.m.s. 0.013 Å). The crystal structure is stabilized by π–π stacking interactions (centroid -centroid distance 3.506 (3)Å, Cg =C4/C5/C6/C7/C8/C9 ; Cgⁱ =C4/C5/C6/C7/C8/C9 ; symmetry code (i) x-1, y, z)

Related literature top

For the use of rigid ligands in the formation of metal-organic coordination polymers, see: Chen et al. (2006); Yang et al. (2009).

Experimental top

White prism-shaped single crystals of 9,10-dihydro-7H-benzo[de]imidazo[2,1-a]-isoquinolin-7-one were initially obtained from the hydrothermal reaction of Naphthalene-1,8-dicarboxylic anhydride (0.3 g), ethylenediamine (5 ml) and H₂O (10 ml) using Teflon lined bomb at 160°C for 5 days and then cooled to room temperature. A few single crystals suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

9,10-Dihydro-7H-benzo[de]imidazo[2,1-a]isoquinolin-7-one top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 464
M_r = 222.24	D_x = 1.448 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 946 reflections
a = 4.4949 (2) Å	θ = 2.7–19.8°
b = 14.9891 (9) Å	µ = 0.09 mm⁻¹
c = 15.1357 (8) Å	T = 296 K
V = 1019.76 (9) Å³	Prism, colourless
Z = 4	0.20 × 0.05 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1837 independent reflections
Radiation source: fine-focus sealed tube	1207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 83.33 pixels mm^-1	θ_max = 25.5°, θ_min = 1.9°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→16
T_min = 0.982, T_max = 0.995	l = −18→16
8736 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0818P)² + 0.9931P] where P = (F_o² + 2F_c²)/3
1837 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³
1 constraint

Crystal data top

C₁₄H₁₀N₂O	V = 1019.76 (9) Å³
M_r = 222.24	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.4949 (2) Å	µ = 0.09 mm⁻¹
b = 14.9891 (9) Å	T = 296 K
c = 15.1357 (8) Å	0.20 × 0.05 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1837 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1207 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.995	R_int = 0.046
8736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	1 restraint
wR(F²) = 0.202	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
1837 reflections	Δρ_min = −0.33 e Å⁻³
154 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	0.8099 (9)	0.5958 (3)	0.5858 (3)	0.0586 (11)
C9	0.4344 (11)	0.4484 (3)	0.5830 (3)	0.0526 (11)
C10	0.5848 (10)	0.4693 (3)	0.6615 (3)	0.0537 (11)
C12	0.6647 (12)	0.5790 (3)	0.5059 (3)	0.0614 (14)
C11	0.7765 (11)	0.5470 (3)	0.6614 (3)	0.0556 (11)
C5	0.0907 (13)	0.3543 (4)	0.4989 (4)	0.0772 (17)
H5	−0.0366	0.3055	0.4963	0.093*
C1	0.5498 (12)	0.4169 (4)	0.7347 (3)	0.0692 (14)
H1	0.6487	0.4308	0.7868	0.083*
O1	0.7130 (11)	0.6295 (2)	0.4429 (2)	0.0886 (14)
C8	0.4680 (11)	0.5014 (3)	0.5046 (3)	0.0557 (12)
C4	0.2423 (12)	0.3730 (3)	0.5796 (3)	0.0620 (13)
C7	0.3183 (12)	0.4788 (4)	0.4287 (3)	0.0673 (14)
H7	0.3457	0.5130	0.3781	0.081*
N2	0.9310 (11)	0.5775 (3)	0.7269 (3)	0.0773 (13)
C3	0.2118 (14)	0.3213 (4)	0.6554 (4)	0.0774 (16)
H3	0.0863	0.2720	0.6547	0.093*
C13	1.0057 (13)	0.6648 (3)	0.6011 (4)	0.0778 (17)
H13A	0.9115	0.7223	0.5921	0.093*
H13B	1.1794	0.6604	0.5633	0.093*
C6	0.1267 (13)	0.4058 (4)	0.4255 (4)	0.0805 (17)
H6	0.0242	0.3924	0.3738	0.097*
C2	0.3623 (14)	0.3418 (4)	0.7303 (4)	0.0825 (18)
H2	0.3413	0.3055	0.7797	0.099*
C14	1.0800 (16)	0.6516 (4)	0.6897 (5)	0.100 (2)
H14A	1.0297	0.7048	0.7230	0.120*
H14B	1.2931	0.6425	0.6945	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.061 (3)	0.056 (2)	0.060 (3)	0.003 (2)	0.006 (2)	−0.006 (2)
C9	0.052 (3)	0.054 (3)	0.051 (3)	0.013 (2)	0.011 (2)	−0.003 (2)
C10	0.050 (2)	0.061 (3)	0.051 (3)	0.012 (2)	0.006 (2)	0.002 (2)
C12	0.068 (3)	0.054 (3)	0.062 (3)	0.016 (3)	0.011 (3)	0.002 (2)
C11	0.047 (3)	0.061 (3)	0.059 (3)	0.010 (3)	0.005 (2)	−0.008 (2)
C5	0.057 (3)	0.079 (4)	0.095 (5)	−0.001 (3)	0.011 (3)	−0.028 (3)
C1	0.066 (3)	0.083 (4)	0.059 (3)	0.018 (3)	0.007 (3)	0.005 (3)
O1	0.118 (3)	0.074 (2)	0.074 (2)	0.006 (3)	0.021 (3)	0.021 (2)
C8	0.050 (3)	0.058 (2)	0.060 (3)	0.014 (2)	0.003 (2)	0.001 (2)
C4	0.051 (3)	0.060 (3)	0.075 (3)	0.009 (3)	0.011 (3)	−0.008 (3)
C7	0.067 (3)	0.081 (4)	0.054 (3)	0.015 (3)	0.000 (3)	−0.004 (3)
N2	0.077 (3)	0.081 (3)	0.074 (3)	0.003 (3)	−0.007 (3)	−0.014 (2)
C3	0.070 (4)	0.067 (3)	0.095 (4)	0.006 (3)	0.023 (3)	0.007 (3)
C13	0.068 (4)	0.059 (3)	0.106 (5)	0.011 (3)	0.019 (3)	−0.020 (3)
C6	0.072 (4)	0.098 (4)	0.072 (4)	0.005 (4)	−0.008 (3)	−0.023 (4)
C2	0.081 (4)	0.084 (4)	0.083 (4)	0.014 (3)	0.019 (3)	0.024 (3)
C14	0.083 (4)	0.097 (5)	0.120 (6)	0.010 (4)	0.015 (4)	−0.041 (4)

Geometric parameters (Å, º) top

N1—C11	1.367 (5)	C1—H1	0.9300
N1—C13	1.377 (6)	C8—C7	1.375 (7)
N1—C12	1.397 (6)	C4—C3	1.391 (7)
C9—C10	1.402 (6)	C7—C6	1.392 (7)
C9—C4	1.423 (6)	C7—H7	0.9300
C9—C8	1.436 (6)	N2—C14	1.414 (8)
C10—C1	1.367 (7)	C3—C2	1.355 (8)
C10—C11	1.448 (6)	C3—H3	0.9300
C12—O1	1.236 (5)	C13—C14	1.396 (8)
C12—C8	1.462 (7)	C13—H13A	0.9700
C11—N2	1.295 (6)	C13—H13B	0.9700
C5—C6	1.363 (8)	C6—H6	0.9300
C5—C4	1.426 (7)	C2—H2	0.9300
C5—H5	0.9300	C14—H14A	0.9700
C1—C2	1.408 (8)	C14—H14B	0.9700

C11—N1—C13	109.4 (4)	C9—C4—C5	118.5 (5)
C11—N1—C12	125.2 (4)	C8—C7—C6	121.7 (5)
C13—N1—C12	125.4 (5)	C8—C7—H7	119.2
C10—C9—C4	120.1 (4)	C6—C7—H7	119.2
C10—C9—C8	121.7 (4)	C11—N2—C14	103.1 (5)
C4—C9—C8	118.2 (4)	C2—C3—C4	121.0 (6)
C1—C10—C9	120.2 (5)	C2—C3—H3	119.5
C1—C10—C11	122.1 (5)	C4—C3—H3	119.5
C9—C10—C11	117.8 (4)	N1—C13—C14	102.0 (5)
O1—C12—N1	118.4 (5)	N1—C13—H13A	111.4
O1—C12—C8	125.7 (5)	C14—C13—H13A	111.4
N1—C12—C8	116.0 (4)	N1—C13—H13B	111.4
N2—C11—N1	113.1 (4)	C14—C13—H13B	111.4
N2—C11—C10	127.0 (5)	H13A—C13—H13B	109.2
N1—C11—C10	119.8 (4)	C5—C6—C7	119.3 (5)
C6—C5—C4	122.0 (6)	C5—C6—H6	120.3
C6—C5—H5	119.0	C7—C6—H6	120.3
C4—C5—H5	119.0	C3—C2—C1	121.3 (5)
C10—C1—C2	119.3 (5)	C3—C2—H2	119.3
C10—C1—H1	120.3	C1—C2—H2	119.3
C2—C1—H1	120.3	C13—C14—N2	112.4 (6)
C7—C8—C9	120.2 (5)	C13—C14—H14A	109.1
C7—C8—C12	120.3 (5)	N2—C14—H14A	109.1
C9—C8—C12	119.6 (4)	C13—C14—H14B	109.1
C3—C4—C9	118.1 (5)	N2—C14—H14B	109.1
C3—C4—C5	123.4 (6)	H14A—C14—H14B	107.9

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.4949 (2), 14.9891 (9), 15.1357 (8)
V (Å³)	1019.76 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.05 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	8736, 1837, 1207
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.202, 1.01
No. of reflections	1837
No. of parameters	154
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.33

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, J.-M., Sun, J.-J., Huang, W.-W., Lao, Y.-N. & Yang, S.-P. (2006). Acta Cryst. E62, m2573–m2574. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Yang, H., Lao, Y. N., Chen, J. M., Wu, H. X. & Yang, S. P. (2009). Eur. J. Inorg. Chem. pp. 2817–2824. Web of Science CSD CrossRef Google Scholar