3a,11b-Dihydr­oxy-2-oxo-2,3,3a,11b-tetra­hydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride

Huang, Y.; Chen, M.-H.; Zhang, Y.-Q.; Xue, S.-F.; Tao, Z.

doi:10.1107/S160053680802093X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1489

doi:10.1107/S160053680802093X

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3a,11b-Dihydroxy-2-oxo-2,3,3a,11b-tetrahydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride

Ying Huang,^a Ming-Hua Chen,^a Yun-Qian Zhang,^a Sai-Feng Xue ^a and Zhu Tao ^b ^*

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: sci.yqzhang@gzu.edu.cn

(Received 7 June 2008; accepted 7 July 2008; online 16 July 2008)

In the crystal structure of the title compound, C₁₃H₁₁N₄O₃⁺·Cl⁻, the dihedral angle between the two pyridine rings is 9.72 (9) Å. Ions are linked via N—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background, see: Zhao et al. (2004 ); Zheng et al. (2005 ).

Experimental

Crystal data

C₁₃H₁₁N₄O₃⁺·Cl⁻
M_r = 306.71
Monoclinic, P 2₁ /c
a = 7.9420 (13) Å
b = 20.352 (3) Å
c = 8.2972 (14) Å
β = 106.620 (5)°
V = 1285.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 (2) K
0.31 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.909, T_max = 0.943
13480 measured reflections
2261 independent reflections
2094 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.05
2261 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.86	2.41	3.1512 (17)	145
N3—H3A⋯O2ⁱⁱ	0.86	2.65	3.146 (2)	118
N4—H4⋯Cl1ⁱⁱⁱ	0.86	2.50	3.2490 (16)	147
O2—H2A⋯Cl1	0.82	2.28	3.0712 (15)	163
O3—H3B⋯O1^iv	0.82	1.89	2.6867 (18)	165
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802093X/at2573sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802093X/at2573Isup2.hkl

checkCIF report

Comment top

Recent year, we used different alkyl-substituted glycolurils as the building blocks to synthesize the partially alkyl substituted cucurbit[n]urils (Zhao et al., 2004; Zheng et al., 2005). In this work, we further report the crystal structure of a phenanthroline-substituted semi-glycoluril.

In the title compound (I), (Fig. 1), consists of organic cations, Cl^- anions. The dihedral angle between two pyridine rings is 9.72 (9) Å. Molecules are linked via N—H···Cl, O—H···Cl and O—H···O hydrogen bonds forming a three-dimensional framework. (Table 1).

Related literature top

For general background, see: Zhao et al.,(2004); Zheng et al.,(2005).

Experimental top

1,10-Phenanthroline-5,6-dione (3.00 g,14.29 mmol) and carbamide (15.00 g, 250 mmol) were dissolved in acetic acid glacial (120 mL) and hydrochloric acid (5 mL) at room temperature. There was a lot of deposit after the mixture were stirred 5 h. Filtrate, solid was washed by ethanol, drying, gained white powder 2.46 g [yield: 63%].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

3a,11b-Dihydroxy-2-oxo-2,3,3a,11b-tetrahydro-1H- imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride top

Crystal data top

C₁₃H₁₁N₄O₃⁺·Cl⁻	F(000) = 632
M_r = 306.71	D_x = 1.585 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2261 reflections
a = 7.9420 (13) Å	θ = 2.0–25.0°
b = 20.352 (3) Å	µ = 0.31 mm⁻¹
c = 8.2972 (14) Å	T = 293 K
β = 106.620 (5)°	Prism, colourless
V = 1285.1 (4) Å³	0.31 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2261 independent reflections
Radiation source: fine-focus sealed tube	2094 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
T_min = 0.909, T_max = 0.943	k = −24→24
13480 measured reflections	l = −9→8

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0589P)² + 0.7326P] where P = (F_o² + 2F_c²)/3
2261 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₃H₁₁N₄O₃⁺·Cl⁻	V = 1285.1 (4) Å³
M_r = 306.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9420 (13) Å	µ = 0.31 mm⁻¹
b = 20.352 (3) Å	T = 293 K
c = 8.2972 (14) Å	0.31 × 0.22 × 0.19 mm
β = 106.620 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2261 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2094 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.943	R_int = 0.022
13480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.48 e Å⁻³
2261 reflections	Δρ_min = −0.52 e Å⁻³
190 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
C1	−0.0113 (3)	0.58542 (11)	0.2547 (3)	0.0409 (5)
H1	−0.0891	0.5658	0.1616	0.049*
C2	−0.0166 (3)	0.65219 (11)	0.2779 (3)	0.0446 (5)
H2	−0.0982	0.6781	0.2015	0.054*
C3	0.1010 (2)	0.68003 (10)	0.4159 (3)	0.0376 (5)
H3	0.0960	0.7249	0.4352	0.045*
C4	0.2275 (2)	0.64158 (9)	0.5271 (2)	0.0280 (4)
C5	0.3591 (2)	0.67304 (8)	0.6779 (2)	0.0288 (4)
C6	0.6083 (2)	0.70941 (8)	0.6106 (2)	0.0286 (4)
C7	0.5217 (2)	0.62729 (8)	0.7653 (2)	0.0265 (4)
C8	0.4878 (2)	0.55393 (8)	0.7408 (2)	0.0250 (4)
C9	0.6001 (2)	0.50849 (9)	0.8421 (2)	0.0311 (4)
H9	0.6963	0.5226	0.9282	0.037*
C10	0.5678 (2)	0.44209 (9)	0.8141 (2)	0.0325 (4)
H10	0.6423	0.4111	0.8805	0.039*
C11	0.4231 (3)	0.42256 (9)	0.6860 (2)	0.0327 (4)
H11	0.4009	0.3778	0.6693	0.039*
C12	0.3479 (2)	0.52914 (8)	0.6134 (2)	0.0258 (4)
C13	0.2261 (2)	0.57459 (8)	0.5007 (2)	0.0261 (4)
N1	0.10578 (19)	0.54886 (8)	0.36612 (19)	0.0314 (4)
H1A	0.1046	0.5070	0.3516	0.038*
N2	0.3139 (2)	0.46487 (7)	0.58529 (19)	0.0315 (4)
N3	0.44790 (19)	0.72802 (7)	0.6258 (2)	0.0337 (4)
H3A	0.4054	0.7671	0.6071	0.040*
N4	0.64752 (19)	0.64940 (7)	0.68046 (18)	0.0284 (3)
H4	0.7373	0.6268	0.6752	0.034*
O1	0.70045 (17)	0.74179 (6)	0.54285 (17)	0.0374 (3)
O2	0.26989 (17)	0.69570 (7)	0.79061 (17)	0.0389 (3)
H2A	0.2216	0.6647	0.8224	0.058*
O3	0.58135 (18)	0.63742 (6)	0.93855 (15)	0.0355 (3)
H3B	0.6013	0.6766	0.9577	0.053*
Cl1	0.03122 (6)	0.58193 (2)	0.83116 (6)	0.03931 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0294 (10)	0.0529 (13)	0.0332 (10)	−0.0040 (9)	−0.0026 (8)	0.0010 (9)
C2	0.0330 (10)	0.0466 (12)	0.0450 (12)	0.0029 (9)	−0.0037 (9)	0.0121 (10)
C3	0.0304 (10)	0.0314 (10)	0.0473 (12)	0.0010 (8)	0.0053 (8)	0.0062 (8)
C4	0.0242 (9)	0.0289 (9)	0.0305 (9)	−0.0007 (7)	0.0073 (7)	0.0014 (7)
C5	0.0289 (9)	0.0228 (8)	0.0336 (10)	−0.0010 (7)	0.0071 (7)	−0.0031 (7)
C6	0.0302 (9)	0.0226 (8)	0.0285 (9)	−0.0043 (7)	0.0014 (7)	−0.0017 (7)
C7	0.0274 (9)	0.0252 (9)	0.0239 (8)	−0.0032 (7)	0.0028 (7)	−0.0008 (7)
C8	0.0270 (8)	0.0242 (9)	0.0239 (8)	−0.0019 (7)	0.0074 (7)	0.0005 (6)
C9	0.0308 (9)	0.0313 (9)	0.0282 (9)	−0.0021 (7)	0.0037 (7)	0.0017 (7)
C10	0.0357 (10)	0.0285 (9)	0.0331 (10)	0.0041 (8)	0.0099 (8)	0.0067 (8)
C11	0.0402 (10)	0.0225 (9)	0.0369 (10)	−0.0016 (7)	0.0133 (8)	0.0001 (7)
C12	0.0266 (8)	0.0247 (8)	0.0270 (9)	−0.0017 (7)	0.0092 (7)	−0.0021 (7)
C13	0.0230 (8)	0.0296 (9)	0.0255 (9)	−0.0025 (7)	0.0065 (7)	−0.0014 (7)
N1	0.0281 (8)	0.0325 (8)	0.0305 (8)	−0.0031 (6)	0.0031 (6)	−0.0043 (6)
N2	0.0337 (8)	0.0258 (8)	0.0328 (8)	−0.0031 (6)	0.0061 (6)	−0.0036 (6)
N3	0.0296 (8)	0.0197 (7)	0.0488 (10)	0.0004 (6)	0.0065 (7)	0.0035 (7)
N4	0.0258 (7)	0.0233 (7)	0.0348 (8)	0.0006 (6)	0.0064 (6)	0.0037 (6)
O1	0.0358 (7)	0.0304 (7)	0.0443 (8)	−0.0045 (6)	0.0088 (6)	0.0097 (6)
O2	0.0381 (7)	0.0349 (7)	0.0468 (8)	−0.0022 (6)	0.0172 (6)	−0.0118 (6)
O3	0.0482 (8)	0.0293 (7)	0.0239 (7)	−0.0074 (6)	0.0021 (6)	−0.0027 (5)
Cl1	0.0309 (3)	0.0414 (3)	0.0425 (3)	−0.00238 (18)	0.0053 (2)	−0.0005 (2)

Geometric parameters (Å, º) top

C1—N1	1.335 (3)	C7—C8	1.520 (2)
C1—C2	1.375 (3)	C8—C9	1.388 (2)
C1—H1	0.9300	C8—C12	1.391 (2)
C2—C3	1.376 (3)	C9—C10	1.383 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.394 (3)	C10—C11	1.382 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C13	1.380 (2)	C11—N2	1.333 (2)
C4—C5	1.523 (2)	C11—H11	0.9300
C5—O2	1.403 (2)	C12—N2	1.342 (2)
C5—N3	1.453 (2)	C12—C13	1.466 (2)
C5—C7	1.589 (2)	C13—N1	1.350 (2)
C6—O1	1.233 (2)	N1—H1A	0.8600
C6—N4	1.350 (2)	N3—H3A	0.8600
C6—N3	1.369 (2)	N4—H4	0.8600
C7—O3	1.394 (2)	O2—H2A	0.8200
C7—N4	1.449 (2)	O3—H3B	0.8200

N1—C1—C2	119.82 (18)	C12—C8—C7	122.01 (15)
N1—C1—H1	120.1	C10—C9—C8	119.56 (17)
C2—C1—H1	120.1	C10—C9—H9	120.2
C1—C2—C3	118.87 (19)	C8—C9—H9	120.2
C1—C2—H2	120.6	C11—C10—C9	118.93 (17)
C3—C2—H2	120.6	C11—C10—H10	120.5
C2—C3—C4	120.59 (19)	C9—C10—H10	120.5
C2—C3—H3	119.7	N2—C11—C10	123.04 (16)
C4—C3—H3	119.7	N2—C11—H11	118.5
C13—C4—C3	118.54 (17)	C10—C11—H11	118.5
C13—C4—C5	121.21 (16)	N2—C12—C8	124.23 (16)
C3—C4—C5	120.21 (16)	N2—C12—C13	116.16 (15)
O2—C5—N3	109.01 (14)	C8—C12—C13	119.61 (15)
O2—C5—C4	109.09 (14)	N1—C13—C4	119.09 (16)
N3—C5—C4	110.92 (15)	N1—C13—C12	117.68 (15)
O2—C5—C7	112.82 (15)	C4—C13—C12	123.23 (16)
N3—C5—C7	100.76 (13)	C1—N1—C13	122.99 (17)
C4—C5—C7	113.94 (14)	C1—N1—H1A	118.5
O1—C6—N4	125.80 (17)	C13—N1—H1A	118.5
O1—C6—N3	125.70 (16)	C11—N2—C12	117.26 (16)
N4—C6—N3	108.49 (15)	C6—N3—C5	110.99 (14)
O3—C7—N4	112.13 (14)	C6—N3—H3A	124.5
O3—C7—C8	106.15 (13)	C5—N3—H3A	124.5
N4—C7—C8	111.12 (14)	C6—N4—C7	112.54 (15)
O3—C7—C5	112.10 (14)	C6—N4—H4	123.7
N4—C7—C5	100.35 (13)	C7—N4—H4	123.7
C8—C7—C5	115.14 (14)	C5—O2—H2A	109.5
C9—C8—C12	116.98 (16)	C7—O3—H3B	109.5
C9—C8—C7	120.98 (15)

N1—C1—C2—C3	0.5 (3)	C9—C8—C12—N2	1.3 (3)
C1—C2—C3—C4	2.3 (3)	C7—C8—C12—N2	179.10 (16)
C2—C3—C4—C13	−3.4 (3)	C9—C8—C12—C13	−179.17 (16)
C2—C3—C4—C5	178.93 (18)	C7—C8—C12—C13	−1.4 (2)
C13—C4—C5—O2	−110.16 (18)	C3—C4—C13—N1	1.7 (3)
C3—C4—C5—O2	67.4 (2)	C5—C4—C13—N1	179.35 (15)
C13—C4—C5—N3	129.75 (17)	C3—C4—C13—C12	−177.36 (17)
C3—C4—C5—N3	−52.7 (2)	C5—C4—C13—C12	0.3 (3)
C13—C4—C5—C7	16.9 (2)	N2—C12—C13—N1	−8.7 (2)
C3—C4—C5—C7	−165.51 (16)	C8—C12—C13—N1	171.79 (15)
O2—C5—C7—O3	−21.6 (2)	N2—C12—C13—C4	170.44 (16)
N3—C5—C7—O3	94.51 (16)	C8—C12—C13—C4	−9.1 (3)
C4—C5—C7—O3	−146.68 (15)	C2—C1—N1—C13	−2.3 (3)
O2—C5—C7—N4	−140.73 (14)	C4—C13—N1—C1	1.1 (3)
N3—C5—C7—N4	−24.66 (16)	C12—C13—N1—C1	−179.75 (17)
C4—C5—C7—N4	94.16 (16)	C10—C11—N2—C12	−0.7 (3)
O2—C5—C7—C8	99.91 (17)	C8—C12—N2—C11	−0.6 (3)
N3—C5—C7—C8	−144.01 (14)	C13—C12—N2—C11	179.89 (16)
C4—C5—C7—C8	−25.2 (2)	O1—C6—N3—C5	167.40 (17)
O3—C7—C8—C9	−39.1 (2)	N4—C6—N3—C5	−12.0 (2)
N4—C7—C8—C9	83.02 (19)	O2—C5—N3—C6	142.10 (15)
C5—C7—C8—C9	−163.78 (16)	C4—C5—N3—C6	−97.76 (17)
O3—C7—C8—C12	143.18 (16)	C7—C5—N3—C6	23.22 (18)
N4—C7—C8—C12	−94.67 (19)	O1—C6—N4—C7	173.90 (17)
C5—C7—C8—C12	18.5 (2)	N3—C6—N4—C7	−6.7 (2)
C12—C8—C9—C10	−0.8 (3)	O3—C7—N4—C6	−98.97 (17)
C7—C8—C9—C10	−178.56 (16)	C8—C7—N4—C6	142.41 (15)
C8—C9—C10—C11	−0.4 (3)	C5—C7—N4—C6	20.17 (17)
C9—C10—C11—N2	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.86	2.41	3.1512 (17)	145
N3—H3A···O2ⁱⁱ	0.86	2.65	3.146 (2)	118
N4—H4···Cl1ⁱⁱⁱ	0.86	2.50	3.2490 (16)	147
O2—H2A···Cl1	0.82	2.28	3.0712 (15)	163
O3—H3B···O1^iv	0.82	1.89	2.6867 (18)	165

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₄O₃⁺·Cl⁻
M_r	306.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9420 (13), 20.352 (3), 8.2972 (14)
β (°)	106.620 (5)
V (Å³)	1285.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.31 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.909, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	13480, 2261, 2094
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.103, 1.05
No. of reflections	2261
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.52

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.86	2.41	3.1512 (17)	144.9
N3—H3A···O2ⁱⁱ	0.86	2.65	3.146 (2)	118.1
N4—H4···Cl1ⁱⁱⁱ	0.86	2.50	3.2490 (16)	146.7
O2—H2A···Cl1	0.82	2.28	3.0712 (15)	162.7
O3—H3B···O1^iv	0.82	1.89	2.6867 (18)	164.9

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) x, −y+3/2, z+1/2.

Acknowledgements

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.

References

Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y. J., Xue, S. F., Zhu, Q. J., Tao, Z., Zhang, J. X., Wei, Z. B., Long, L. S., Hu, M. L., Xiao, H. P. & Day, A. I. (2004). Chin. Sci. Bull. 49, 1111–1116. Web of Science CSD CrossRef CAS Google Scholar
Zheng, L. M., Zhu, J. N., Zhang, Y. Q., Tao, Z., Xue, S. F., Zhu, Q. J., Wei, Z. B. & Long, L. S. (2005). Chin. J. Inorg. Chem. 21, 1583–1588. CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1489

doi:10.1107/S160053680802093X

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

3a,11b-Dihydr­­oxy-2-oxo-2,3,3a,11b-tetra­hydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3a,11b-Dihydroxy-2-oxo-2,3,3a,11b-tetrahydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride