6-Oxobenz[de]isoquinolino[2,1-a]benzimidazolium chloride monohydrate

Jian, F.-F.; Du, L.; Wang, J.

doi:10.1107/S1600536807061582

organic compounds

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Volume 64| Part 1| January 2008| Page o7

https://doi.org/10.1107/S1600536807061582

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6-Oxobenz[de]isoquinolino[2,1-a]benzimidazolium chloride monohydrate

Fang-Fang Jian,^a ^* Li Du ^a and Jing Wang ^a

^aNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: ffj2003@163169.net

(Received 16 November 2007; accepted 21 November 2007; online 6 December 2007)

The title compound, C₁₈H₁₁N₂O⁺·Cl⁻·H₂O, was prepared by the reaction of 1,8-naphthalic anhydride with o-phenylenediamine in DMF. The dihedral angle formed by the phenyl and naphthalic rings is 177.06°. The structure is stabilized by intramolecular C—H⋯O hydrogen bonds. There are N—H⋯Cl, O—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds in the structure.

Related literature

For related literature, see: Ofir (2006 ). Cederfur et al. (2003 ).

Experimental

Crystal data

C₁₈H₁₁N₂O⁺·Cl⁻·H₂O
M_r = 324.75
Triclinic, $[P \overline 1]$
a = 8.9000 (18) Å
b = 8.9440 (18) Å
c = 9.4480 (19) Å
α = 81.50 (3)°
β = 88.76 (3)°
γ = 77.61 (3)°
V = 726.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 295 (2) K
0.3 × 0.25 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8800 measured reflections
2698 independent reflections
1852 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.02
2698 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.86	2.19	3.044 (2)	175
O2—H2C⋯Cl1	0.85	2.48	3.253 (3)	153
O2—H2D⋯Cl1ⁱ	0.85	2.35	3.195 (2)	171
C5—H5A⋯O1	0.93	2.48	2.964 (3)	113
C5—H5A⋯O1ⁱⁱ	0.93	2.47	3.153 (2)	130
C9—H9A⋯Cl1	0.93	2.78	3.673 (2)	162
C15—H15A⋯O2ⁱⁱⁱ	0.93	2.58	3.313 (3)	136
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) -x, -y+2, -z+1; (iii) x+1, y, z-1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807061582/lw2048sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061582/lw2048Isup2.hkl

checkCIF report

Comment top

1,8-Naphthlimide derivatives are an important function material during the recent years and are used as optical characters. 1,8-Naphthalimides exhibit hydrogen-bonding. and cation-dependent fluorescence. The naphthyl group can be used as a good receptor(Cederfur et al., 2003).

In the title compound, the bond lengths and angles are normal in the 1,8-naphthalenedicarboximide and phenyl ring (Ofir, 2006). The dihedral angle formed by the phenyl(C1—C6) ring and naphthalic ring(N1—C18) is 177.06°.

There are π-π stacking interactions in the molecular in the structure. The distance between ring centroids Cg(1)—Cg(5)(i) are 3.578 (2); Cg(2)—Cg(2)(i) are 3.648 (2); Cg(2)—Cg(5)(i) are 3.845 (2) [symmetry code:i=-x,1 - y,1 - z].where Cg1 is the centre-of-gravity of the ring defined by atoms (N1—C6—C1—C2—C7), Cg2 is the centre-of-gravity of the ring defined by atoms (N1—C7—C8—C17—C16—C18) and Cg5 is the centre-of-gravity of the ring defined by atoms (C12—C13—C14—C15—C16—C17).

The crystal packing is stabilized by N2—H2A···Cl,O2—H2C···Cl1, C5—H5A···O1, C9—H9A···Cl1, C15—H15···O2 and O2- H2D···Cl1 hydrogen bonds. (Table 2).

Related literature top

For related literature, see: Ofir (2006). Cederfur et al. (2003)

Experimental top

The single crystals of the title compound were obtained by reaction o-phenylene diamine(0.2 mmol) with 1,8-naphthalic anhydride (0.2 mmol) in refluxing DMF(50 ml). The product (yield 87%) was stirred in the DMF. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from DMF and HCl 4:1 (v/v) solution at room temperature.

Structure description top

The crystal packing is stabilized by N2—H2A···Cl,O2—H2C···Cl1, C5—H5A···O1, C9—H9A···Cl1, C15—H15···O2 and O2- H2D···Cl1 hydrogen bonds. (Table 2).

For related literature, see: Ofir (2006). Cederfur et al. (2003)

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.

6-Oxobenz[de]isoquinolino[2,1-a]benzimidazolium chloride monohydrate top

Crystal data top

C₁₈H₁₁N₂O⁺·Cl⁻·H₂O	Z = 2
M_r = 324.75	F(000) = 336
Triclinic, P1	D_x = 1.485 Mg m⁻³
Hall symbol: -P 1	Melting point: 210 K
a = 8.9000 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9440 (18) Å	Cell parameters from 512 reflections
c = 9.4480 (19) Å	θ = 2–22°
α = 81.50 (3)°	µ = 0.28 mm⁻¹
β = 88.76 (3)°	T = 295 K
γ = 77.61 (3)°	Block, colorless
V = 726.5 (3) Å³	0.3 × 0.25 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1852 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 25.5°, θ_min = 2.2°
phi and ω scans	h = −10→10
8800 measured reflections	k = −8→10
2698 independent reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.048P)² + 0.1865P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2698 reflections	Δρ_max = 0.20 e Å⁻³
209 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Crystal data top

C₁₈H₁₁N₂O⁺·Cl⁻·H₂O	γ = 77.61 (3)°
M_r = 324.75	V = 726.5 (3) Å³
Triclinic, P1	Z = 2
a = 8.9000 (18) Å	Mo Kα radiation
b = 8.9440 (18) Å	µ = 0.28 mm⁻¹
c = 9.4480 (19) Å	T = 295 K
α = 81.50 (3)°	0.3 × 0.25 × 0.2 mm
β = 88.76 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1852 reflections with I > 2σ(I)
8800 measured reflections	R_int = 0.041
2698 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2698 reflections	Δρ_min = −0.25 e Å⁻³
209 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
O1	0.1171 (2)	0.7662 (2)	0.52217 (19)	0.0619 (5)
N1	−0.0148 (2)	0.6439 (2)	0.69142 (19)	0.0415 (5)
N2	−0.1494 (2)	0.5542 (2)	0.8640 (2)	0.0467 (5)
H2A	−0.1834	0.4913	0.9281	0.056*
C1	−0.2061 (3)	0.7127 (3)	0.8379 (2)	0.0444 (6)
C2	−0.3250 (3)	0.8054 (3)	0.8995 (3)	0.0583 (7)
H2B	−0.3835	0.7655	0.9724	0.070*
C3	−0.3523 (3)	0.9601 (3)	0.8470 (3)	0.0614 (7)
H3A	−0.4322	1.0273	0.8850	0.074*
C4	−0.2649 (3)	1.0189 (3)	0.7400 (3)	0.0570 (7)
H4A	−0.2866	1.1249	0.7089	0.068*
C5	−0.1473 (3)	0.9268 (3)	0.6777 (3)	0.0493 (6)
H5A	−0.0893	0.9670	0.6044	0.059*
C6	−0.1196 (2)	0.7714 (3)	0.7295 (2)	0.0428 (6)
C7	−0.0361 (2)	0.5140 (3)	0.7766 (2)	0.0418 (5)
C8	0.0551 (3)	0.3648 (3)	0.7634 (2)	0.0453 (6)
C9	0.0314 (3)	0.2316 (3)	0.8436 (3)	0.0570 (7)
H9A	−0.0465	0.2362	0.9112	0.068*
C10	0.1232 (3)	0.0895 (3)	0.8245 (3)	0.0666 (8)
H10A	0.1067	−0.0004	0.8799	0.080*
C11	0.2356 (3)	0.0807 (3)	0.7269 (3)	0.0650 (8)
H11A	0.2955	−0.0156	0.7155	0.078*
C12	0.2643 (3)	0.2142 (3)	0.6415 (3)	0.0548 (7)
C13	0.3794 (3)	0.2111 (4)	0.5386 (3)	0.0673 (8)
H13A	0.4432	0.1167	0.5273	0.081*
C14	0.4013 (3)	0.3414 (4)	0.4543 (3)	0.0632 (7)
H14A	0.4777	0.3354	0.3854	0.076*
C15	0.3092 (3)	0.4827 (3)	0.4716 (3)	0.0535 (6)
H15A	0.3238	0.5719	0.4136	0.064*
C16	0.1967 (3)	0.4934 (3)	0.5731 (2)	0.0453 (6)
C17	0.1714 (3)	0.3589 (3)	0.6603 (3)	0.0466 (6)
C18	0.1035 (3)	0.6455 (3)	0.5888 (2)	0.0451 (6)
Cl1	−0.26953 (7)	0.34446 (8)	1.10307 (7)	0.0603 (2)
O2	−0.5321 (2)	0.6341 (3)	1.1799 (2)	0.0821 (6)
H2C	−0.4470	0.5687	1.1836	0.098*
H2D	−0.5787	0.6295	1.1035	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0707 (11)	0.0447 (11)	0.0648 (12)	−0.0123 (9)	0.0176 (9)	0.0077 (9)
N1	0.0449 (10)	0.0346 (11)	0.0446 (11)	−0.0109 (9)	−0.0005 (8)	−0.0005 (9)
N2	0.0538 (11)	0.0415 (12)	0.0434 (11)	−0.0150 (9)	0.0040 (9)	0.0047 (9)
C1	0.0478 (13)	0.0382 (14)	0.0448 (13)	−0.0101 (11)	−0.0010 (11)	0.0030 (11)
C2	0.0559 (15)	0.0577 (18)	0.0587 (16)	−0.0110 (13)	0.0133 (13)	−0.0033 (14)
C3	0.0596 (16)	0.0516 (17)	0.0666 (18)	−0.0002 (13)	0.0115 (13)	−0.0064 (14)
C4	0.0608 (16)	0.0401 (15)	0.0655 (17)	−0.0050 (12)	0.0016 (13)	−0.0022 (13)
C5	0.0554 (14)	0.0404 (14)	0.0505 (14)	−0.0126 (12)	0.0036 (12)	0.0013 (11)
C6	0.0422 (12)	0.0393 (14)	0.0462 (14)	−0.0092 (11)	−0.0014 (10)	−0.0030 (11)
C7	0.0457 (12)	0.0367 (13)	0.0429 (13)	−0.0125 (11)	−0.0044 (11)	0.0003 (11)
C8	0.0524 (13)	0.0368 (14)	0.0467 (14)	−0.0119 (11)	−0.0074 (11)	−0.0018 (11)
C9	0.0677 (16)	0.0435 (16)	0.0590 (16)	−0.0141 (13)	−0.0031 (13)	−0.0008 (13)
C10	0.0822 (19)	0.0381 (16)	0.077 (2)	−0.0138 (14)	−0.0093 (16)	0.0011 (14)
C11	0.0748 (18)	0.0391 (16)	0.080 (2)	−0.0058 (14)	−0.0160 (16)	−0.0138 (15)
C12	0.0559 (15)	0.0441 (16)	0.0649 (17)	−0.0056 (12)	−0.0109 (13)	−0.0148 (13)
C13	0.0624 (17)	0.0588 (19)	0.082 (2)	−0.0009 (14)	−0.0076 (16)	−0.0301 (17)
C14	0.0557 (16)	0.072 (2)	0.0666 (18)	−0.0134 (15)	0.0056 (13)	−0.0271 (16)
C15	0.0512 (14)	0.0576 (17)	0.0539 (15)	−0.0125 (13)	−0.0013 (12)	−0.0139 (13)
C16	0.0453 (13)	0.0443 (15)	0.0474 (14)	−0.0105 (11)	−0.0028 (11)	−0.0083 (11)
C17	0.0481 (13)	0.0444 (15)	0.0489 (14)	−0.0100 (11)	−0.0100 (11)	−0.0100 (11)
C18	0.0454 (13)	0.0451 (15)	0.0442 (14)	−0.0112 (11)	−0.0011 (11)	−0.0027 (12)
Cl1	0.0674 (4)	0.0554 (5)	0.0554 (4)	−0.0173 (3)	−0.0016 (3)	0.0071 (3)
O2	0.0807 (13)	0.0973 (17)	0.0678 (13)	−0.0119 (12)	0.0008 (11)	−0.0218 (12)

Geometric parameters (Å, º) top

O1—C18	1.195 (3)	C8—C17	1.404 (3)
N1—C7	1.359 (3)	C9—C10	1.389 (4)
N1—C6	1.397 (3)	C9—H9A	0.9300
N1—C18	1.416 (3)	C10—C11	1.344 (4)
N2—C7	1.312 (3)	C10—H10A	0.9300
N2—C1	1.385 (3)	C11—C12	1.407 (4)
N2—H2A	0.8600	C11—H11A	0.9300
C1—C2	1.373 (3)	C12—C13	1.396 (4)
C1—C6	1.377 (3)	C12—C17	1.411 (3)
C2—C3	1.370 (4)	C13—C14	1.359 (4)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.374 (4)	C14—C15	1.381 (4)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.366 (4)	C15—C16	1.369 (3)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.375 (3)	C16—C17	1.412 (3)
C5—H5A	0.9300	C16—C18	1.459 (3)
C7—C8	1.427 (3)	O2—H2C	0.8500
C8—C9	1.369 (3)	O2—H2D	0.8500

C7—N1—C6	108.91 (18)	C8—C9—H9A	119.9
C7—N1—C18	123.8 (2)	C10—C9—H9A	119.9
C6—N1—C18	127.18 (19)	C11—C10—C9	120.7 (3)
C7—N2—C1	110.12 (19)	C11—C10—H10A	119.6
C7—N2—H2A	124.9	C9—C10—H10A	119.6
C1—N2—H2A	124.9	C10—C11—C12	121.2 (3)
C2—C1—C6	122.1 (2)	C10—C11—H11A	119.4
C2—C1—N2	130.9 (2)	C12—C11—H11A	119.4
C6—C1—N2	107.0 (2)	C13—C12—C11	123.4 (3)
C3—C2—C1	116.0 (2)	C13—C12—C17	118.2 (3)
C3—C2—H2B	122.0	C11—C12—C17	118.4 (3)
C1—C2—H2B	122.0	C14—C13—C12	122.2 (3)
C2—C3—C4	121.9 (2)	C14—C13—H13A	118.9
C2—C3—H3A	119.1	C12—C13—H13A	118.9
C4—C3—H3A	119.1	C13—C14—C15	119.5 (3)
C5—C4—C3	122.3 (2)	C13—C14—H14A	120.2
C5—C4—H4A	118.9	C15—C14—H14A	120.2
C3—C4—H4A	118.9	C16—C15—C14	120.9 (3)
C4—C5—C6	116.1 (2)	C16—C15—H15A	119.6
C4—C5—H5A	121.9	C14—C15—H15A	119.6
C6—C5—H5A	121.9	C15—C16—C17	120.2 (2)
C5—C6—C1	121.6 (2)	C15—C16—C18	119.0 (2)
C5—C6—N1	132.6 (2)	C17—C16—C18	120.8 (2)
C1—C6—N1	105.75 (19)	C8—C17—C12	119.2 (2)
N2—C7—N1	108.2 (2)	C8—C17—C16	121.9 (2)
N2—C7—C8	129.9 (2)	C12—C17—C16	118.9 (2)
N1—C7—C8	121.9 (2)	O1—C18—N1	119.1 (2)
C9—C8—C17	120.3 (2)	O1—C18—C16	126.1 (2)
C9—C8—C7	123.0 (2)	N1—C18—C16	114.8 (2)
C17—C8—C7	116.7 (2)	H2C—O2—H2D	107.7
C8—C9—C10	120.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86	2.19	3.044 (2)	175
O2—H2C···Cl1	0.85	2.48	3.253 (3)	153
O2—H2D···Cl1ⁱ	0.85	2.35	3.195 (2)	171
C5—H5A···O1	0.93	2.48	2.964 (3)	113
C5—H5A···O1ⁱⁱ	0.93	2.47	3.153 (2)	130
C9—H9A···Cl1	0.93	2.78	3.673 (2)	162
C15—H15A···O2ⁱⁱⁱ	0.93	2.58	3.313 (3)	136

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁N₂O⁺·Cl⁻·H₂O
M_r	324.75
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.9000 (18), 8.9440 (18), 9.4480 (19)
α, β, γ (°)	81.50 (3), 88.76 (3), 77.61 (3)
V (Å³)	726.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.3 × 0.25 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8800, 2698, 1852
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.02
No. of reflections	2698
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86	2.19	3.044 (2)	175
O2—H2C···Cl1	0.85	2.48	3.253 (3)	153
O2—H2D···Cl1ⁱ	0.85	2.35	3.195 (2)	171
C5—H5A···O1	0.93	2.48	2.964 (3)	113
C5—H5A···O1ⁱⁱ	0.93	2.47	3.153 (2)	130
C9—H9A···Cl1	0.93	2.78	3.673 (2)	162
C15—H15A···O2ⁱⁱⁱ	0.93	2.58	3.313 (3)	136

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

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005B04).

References

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