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organic compounds
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
In the 13H11N4O3+·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.
of the title compound, CExperimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2005); cell 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
10.1107/S160053680802093X/at2573sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680802093X/at2573Isup2.hkl
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%].
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.
Data collection: APEX2 (Bruker, 2005); cell
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). ![]() | Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C13H11N4O3+·Cl− | F(000) = 632 |
Mr = 306.71 | Dx = 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 |
Bruker APEXII CCD area-detector diffractometer | 2261 independent reflections |
Radiation source: fine-focus sealed tube | 2094 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→9 |
Tmin = 0.909, Tmax = 0.943 | k = −24→24 |
13480 measured reflections | l = −9→8 |
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(Fo2) + (0.0589P)2 + 0.7326P] where P = (Fo2 + 2Fc2)/3 |
2261 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C13H11N4O3+·Cl− | V = 1285.1 (4) Å3 |
Mr = 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)° |
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 = 0.943 | Rint = 0.022 |
13480 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.48 e Å−3 |
2261 reflections | Δρmin = −0.52 e Å−3 |
190 parameters |
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 | Uiso*/Ueq | ||
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) |
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) |
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) |
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···O1iv | 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− |
Mr | 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) |
Tmin, Tmax | 0.909, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13480, 2261, 2094 |
Rint | 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 |
Δρmax, Δρmin (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).
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···O1iv | 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
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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).