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

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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

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[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.]); Zheng et al. (2005[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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N4O3+·Cl

  • Mr = 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[Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.909, Tmax = 0.943

  • 13480 measured reflections

  • 2261 independent reflections

  • 2094 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.103

  • S = 1.05

  • 2261 reflections

  • 190 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O1iv 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[Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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%].

Refinement top

H atoms were placed in calculated positions with C—H = 0.93, N—H = 0.86 and O—H = 0.82 Å and refined as riding, with Uiso(H) = 1.2-1.5Ueq.

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
[Figure 1] 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+·ClF(000) = 632
Mr = 306.71Dx = 1.585 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2261 reflections
a = 7.9420 (13) Åθ = 2.0–25.0°
b = 20.352 (3) ŵ = 0.31 mm1
c = 8.2972 (14) ÅT = 293 K
β = 106.620 (5)°Prism, colourless
V = 1285.1 (4) Å30.31 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2261 independent reflections
Radiation source: fine-focus sealed tube2094 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 89
Tmin = 0.909, Tmax = 0.943k = 2424
13480 measured reflectionsl = 98
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.7326P]
where P = (Fo2 + 2Fc2)/3
2261 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C13H11N4O3+·ClV = 1285.1 (4) Å3
Mr = 306.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9420 (13) ŵ = 0.31 mm1
b = 20.352 (3) ÅT = 293 K
c = 8.2972 (14) Å0.31 × 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)
Tmin = 0.909, Tmax = 0.943Rint = 0.022
13480 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.05Δρmax = 0.48 e Å3
2261 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/Ueq
C10.0113 (3)0.58542 (11)0.2547 (3)0.0409 (5)
H10.08910.56580.16160.049*
C20.0166 (3)0.65219 (11)0.2779 (3)0.0446 (5)
H20.09820.67810.20150.054*
C30.1010 (2)0.68003 (10)0.4159 (3)0.0376 (5)
H30.09600.72490.43520.045*
C40.2275 (2)0.64158 (9)0.5271 (2)0.0280 (4)
C50.3591 (2)0.67304 (8)0.6779 (2)0.0288 (4)
C60.6083 (2)0.70941 (8)0.6106 (2)0.0286 (4)
C70.5217 (2)0.62729 (8)0.7653 (2)0.0265 (4)
C80.4878 (2)0.55393 (8)0.7408 (2)0.0250 (4)
C90.6001 (2)0.50849 (9)0.8421 (2)0.0311 (4)
H90.69630.52260.92820.037*
C100.5678 (2)0.44209 (9)0.8141 (2)0.0325 (4)
H100.64230.41110.88050.039*
C110.4231 (3)0.42256 (9)0.6860 (2)0.0327 (4)
H110.40090.37780.66930.039*
C120.3479 (2)0.52914 (8)0.6134 (2)0.0258 (4)
C130.2261 (2)0.57459 (8)0.5007 (2)0.0261 (4)
N10.10578 (19)0.54886 (8)0.36612 (19)0.0314 (4)
H1A0.10460.50700.35160.038*
N20.3139 (2)0.46487 (7)0.58529 (19)0.0315 (4)
N30.44790 (19)0.72802 (7)0.6258 (2)0.0337 (4)
H3A0.40540.76710.60710.040*
N40.64752 (19)0.64940 (7)0.68046 (18)0.0284 (3)
H40.73730.62680.67520.034*
O10.70045 (17)0.74179 (6)0.54285 (17)0.0374 (3)
O20.26989 (17)0.69570 (7)0.79061 (17)0.0389 (3)
H2A0.22160.66470.82240.058*
O30.58135 (18)0.63742 (6)0.93855 (15)0.0355 (3)
H3B0.60130.67660.95770.053*
Cl10.03122 (6)0.58193 (2)0.83116 (6)0.03931 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0294 (10)0.0529 (13)0.0332 (10)0.0040 (9)0.0026 (8)0.0010 (9)
C20.0330 (10)0.0466 (12)0.0450 (12)0.0029 (9)0.0037 (9)0.0121 (10)
C30.0304 (10)0.0314 (10)0.0473 (12)0.0010 (8)0.0053 (8)0.0062 (8)
C40.0242 (9)0.0289 (9)0.0305 (9)0.0007 (7)0.0073 (7)0.0014 (7)
C50.0289 (9)0.0228 (8)0.0336 (10)0.0010 (7)0.0071 (7)0.0031 (7)
C60.0302 (9)0.0226 (8)0.0285 (9)0.0043 (7)0.0014 (7)0.0017 (7)
C70.0274 (9)0.0252 (9)0.0239 (8)0.0032 (7)0.0028 (7)0.0008 (7)
C80.0270 (8)0.0242 (9)0.0239 (8)0.0019 (7)0.0074 (7)0.0005 (6)
C90.0308 (9)0.0313 (9)0.0282 (9)0.0021 (7)0.0037 (7)0.0017 (7)
C100.0357 (10)0.0285 (9)0.0331 (10)0.0041 (8)0.0099 (8)0.0067 (8)
C110.0402 (10)0.0225 (9)0.0369 (10)0.0016 (7)0.0133 (8)0.0001 (7)
C120.0266 (8)0.0247 (8)0.0270 (9)0.0017 (7)0.0092 (7)0.0021 (7)
C130.0230 (8)0.0296 (9)0.0255 (9)0.0025 (7)0.0065 (7)0.0014 (7)
N10.0281 (8)0.0325 (8)0.0305 (8)0.0031 (6)0.0031 (6)0.0043 (6)
N20.0337 (8)0.0258 (8)0.0328 (8)0.0031 (6)0.0061 (6)0.0036 (6)
N30.0296 (8)0.0197 (7)0.0488 (10)0.0004 (6)0.0065 (7)0.0035 (7)
N40.0258 (7)0.0233 (7)0.0348 (8)0.0006 (6)0.0064 (6)0.0037 (6)
O10.0358 (7)0.0304 (7)0.0443 (8)0.0045 (6)0.0088 (6)0.0097 (6)
O20.0381 (7)0.0349 (7)0.0468 (8)0.0022 (6)0.0172 (6)0.0118 (6)
O30.0482 (8)0.0293 (7)0.0239 (7)0.0074 (6)0.0021 (6)0.0027 (5)
Cl10.0309 (3)0.0414 (3)0.0425 (3)0.00238 (18)0.0053 (2)0.0005 (2)
Geometric parameters (Å, º) top
C1—N11.335 (3)C7—C81.520 (2)
C1—C21.375 (3)C8—C91.388 (2)
C1—H10.9300C8—C121.391 (2)
C2—C31.376 (3)C9—C101.383 (3)
C2—H20.9300C9—H90.9300
C3—C41.394 (3)C10—C111.382 (3)
C3—H30.9300C10—H100.9300
C4—C131.380 (2)C11—N21.333 (2)
C4—C51.523 (2)C11—H110.9300
C5—O21.403 (2)C12—N21.342 (2)
C5—N31.453 (2)C12—C131.466 (2)
C5—C71.589 (2)C13—N11.350 (2)
C6—O11.233 (2)N1—H1A0.8600
C6—N41.350 (2)N3—H3A0.8600
C6—N31.369 (2)N4—H40.8600
C7—O31.394 (2)O2—H2A0.8200
C7—N41.449 (2)O3—H3B0.8200
N1—C1—C2119.82 (18)C12—C8—C7122.01 (15)
N1—C1—H1120.1C10—C9—C8119.56 (17)
C2—C1—H1120.1C10—C9—H9120.2
C1—C2—C3118.87 (19)C8—C9—H9120.2
C1—C2—H2120.6C11—C10—C9118.93 (17)
C3—C2—H2120.6C11—C10—H10120.5
C2—C3—C4120.59 (19)C9—C10—H10120.5
C2—C3—H3119.7N2—C11—C10123.04 (16)
C4—C3—H3119.7N2—C11—H11118.5
C13—C4—C3118.54 (17)C10—C11—H11118.5
C13—C4—C5121.21 (16)N2—C12—C8124.23 (16)
C3—C4—C5120.21 (16)N2—C12—C13116.16 (15)
O2—C5—N3109.01 (14)C8—C12—C13119.61 (15)
O2—C5—C4109.09 (14)N1—C13—C4119.09 (16)
N3—C5—C4110.92 (15)N1—C13—C12117.68 (15)
O2—C5—C7112.82 (15)C4—C13—C12123.23 (16)
N3—C5—C7100.76 (13)C1—N1—C13122.99 (17)
C4—C5—C7113.94 (14)C1—N1—H1A118.5
O1—C6—N4125.80 (17)C13—N1—H1A118.5
O1—C6—N3125.70 (16)C11—N2—C12117.26 (16)
N4—C6—N3108.49 (15)C6—N3—C5110.99 (14)
O3—C7—N4112.13 (14)C6—N3—H3A124.5
O3—C7—C8106.15 (13)C5—N3—H3A124.5
N4—C7—C8111.12 (14)C6—N4—C7112.54 (15)
O3—C7—C5112.10 (14)C6—N4—H4123.7
N4—C7—C5100.35 (13)C7—N4—H4123.7
C8—C7—C5115.14 (14)C5—O2—H2A109.5
C9—C8—C12116.98 (16)C7—O3—H3B109.5
C9—C8—C7120.98 (15)
N1—C1—C2—C30.5 (3)C9—C8—C12—N21.3 (3)
C1—C2—C3—C42.3 (3)C7—C8—C12—N2179.10 (16)
C2—C3—C4—C133.4 (3)C9—C8—C12—C13179.17 (16)
C2—C3—C4—C5178.93 (18)C7—C8—C12—C131.4 (2)
C13—C4—C5—O2110.16 (18)C3—C4—C13—N11.7 (3)
C3—C4—C5—O267.4 (2)C5—C4—C13—N1179.35 (15)
C13—C4—C5—N3129.75 (17)C3—C4—C13—C12177.36 (17)
C3—C4—C5—N352.7 (2)C5—C4—C13—C120.3 (3)
C13—C4—C5—C716.9 (2)N2—C12—C13—N18.7 (2)
C3—C4—C5—C7165.51 (16)C8—C12—C13—N1171.79 (15)
O2—C5—C7—O321.6 (2)N2—C12—C13—C4170.44 (16)
N3—C5—C7—O394.51 (16)C8—C12—C13—C49.1 (3)
C4—C5—C7—O3146.68 (15)C2—C1—N1—C132.3 (3)
O2—C5—C7—N4140.73 (14)C4—C13—N1—C11.1 (3)
N3—C5—C7—N424.66 (16)C12—C13—N1—C1179.75 (17)
C4—C5—C7—N494.16 (16)C10—C11—N2—C120.7 (3)
O2—C5—C7—C899.91 (17)C8—C12—N2—C110.6 (3)
N3—C5—C7—C8144.01 (14)C13—C12—N2—C11179.89 (16)
C4—C5—C7—C825.2 (2)O1—C6—N3—C5167.40 (17)
O3—C7—C8—C939.1 (2)N4—C6—N3—C512.0 (2)
N4—C7—C8—C983.02 (19)O2—C5—N3—C6142.10 (15)
C5—C7—C8—C9163.78 (16)C4—C5—N3—C697.76 (17)
O3—C7—C8—C12143.18 (16)C7—C5—N3—C623.22 (18)
N4—C7—C8—C1294.67 (19)O1—C6—N4—C7173.90 (17)
C5—C7—C8—C1218.5 (2)N3—C6—N4—C76.7 (2)
C12—C8—C9—C100.8 (3)O3—C7—N4—C698.97 (17)
C7—C8—C9—C10178.56 (16)C8—C7—N4—C6142.41 (15)
C8—C9—C10—C110.4 (3)C5—C7—N4—C620.17 (17)
C9—C10—C11—N21.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.862.413.1512 (17)145
N3—H3A···O2ii0.862.653.146 (2)118
N4—H4···Cl1iii0.862.503.2490 (16)147
O2—H2A···Cl10.822.283.0712 (15)163
O3—H3B···O1iv0.821.892.6867 (18)165
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+3/2, z1/2; (iii) x+1, y, z; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H11N4O3+·Cl
Mr306.71
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.9420 (13), 20.352 (3), 8.2972 (14)
β (°) 106.620 (5)
V3)1285.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.31 × 0.22 × 0.19
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.909, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
13480, 2261, 2094
Rint0.022
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.103, 1.05
No. of reflections2261
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.862.413.1512 (17)144.9
N3—H3A···O2ii0.862.653.146 (2)118.1
N4—H4···Cl1iii0.862.503.2490 (16)146.7
O2—H2A···Cl10.822.283.0712 (15)162.7
O3—H3B···O1iv0.821.892.6867 (18)164.9
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+3/2, z1/2; (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

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