Literature DB >> 21200947

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

Abstract

The title compound, C(18)H(11)N(2)O(+)·Cl(-)·H(2)O, was prepared by the reaction of 1,8-naphthalic anhydride with o-phenyl-ene-diamine in DMF. The dihedral angle formed by the phenyl and naphthalic rings is 177.06°. The structure is stabilized by intra-molecular 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.

Entities: Chemical Disease Species

Year: 2007 PMID： 21200947 PMCID： PMC2914897 DOI： 10.1107/S1600536807061582

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

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

Experimental

Crystal data

C18H11N2O+·Cl−·H2O M = 324.75 Triclinic, 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[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.112 S = 1.02 2698 reflections 209 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.25 e Å−3 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061582/lw2048sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061582/lw2048Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₁N₂O⁺·Cl^–·H₂O	Z = 2
M_r = 324.75	F₀₀₀ = 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 = 2–22º
α = 81.50 (3)º	µ = 0.28 mm⁻¹
β = 88.76 (3)º	T = 295 (2) K
γ = 77.61 (3)º	Block, colorless
V = 726.5 (3) Å³	0.3 × 0.25 × 0.2 mm

Bruker SMART CCD area-detector diffractometer	1852 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Monochromator: graphite	θ_max = 25.5º
T = 295(2) K	θ_min = 2.2º
phi and ω scans	h = −10→10
Absorption correction: none	k = −8→10
8800 measured reflections	l = −11→11
2698 independent reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.048P)² + 0.1865P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.20 e Å⁻³
2698 reflections	Δρ_min = −0.25 e Å⁻³
209 parameters	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)
Secondary atom site location: difference Fourier map

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	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*

	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)

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)

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

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) ; (ii) ; (iii) .

1 in total

1. Synthesis and screening of a molecularly imprinted polymer library targeted for penicillin G.

Authors: Josefine Cederfur; Yuxin Pei; Meng Zihui; Maria Kempe
Journal: J Comb Chem Date: 2003 Jan-Feb

1 in total