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The 2,8-dihydroxy-1,3,7,9-tetramethyl-6,12-dihydrodipyrido[1,2-
a:1′,2′-
d]pyrazinediylium dication possesses 2/
m symmetry and lies in the mirror plane together with a chloride anion and the water O atom. The dication also lies on an inversion centre,
i.e. C
16H
20N
2O
22+·2Cl
−·2H
2O. Due to these symmetry constrictions the dication adopts an unexpected planar conformation. Molecules are linked by O—H
O and O—H
Cl hydrogen bonds to form chains, which are cross-connected by C—H
Cl attractive interactions forming a complex three-dimensional hydrogen-bond network.
Supporting information
CCDC reference: 150854
Data collection: STADI4 (Stoe & Cie, 1996a); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2000 (Spek, 2000); software used to prepare material for publication: SHELXL97 and PARST96 (Nardelli, 1995).
6,12-Dihydro-2,8-dihydroxy-1,3,7,9-tetramethyl-dipyrido[1,2 - a:1',2'-d]
pyrazinediylium dichloride dihydrate
top
Crystal data top
C16H20N2O22+·2Cl−·2H2O | F(000) = 400 |
Mr = 379.28 | Dx = 1.407 Mg m−3 |
Monoclinic, I2/m | Mo Kα radiation, λ = 0.71073 Å |
a = 11.255 (15) Å | Cell parameters from 10 reflections |
b = 6.8650 (13) Å | θ = 6.4–14.3° |
c = 11.9530 (12) Å | µ = 0.39 mm−1 |
β = 104.15 (2)° | T = 293 K |
V = 895.5 (12) Å3 | Prism, colourless |
Z = 2 | 0.50 × 0.45 × 0.40 mm |
Data collection top
Philips PW1100 upgraded by Stoe & Cie diffractometer | 1146 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.021 |
Graphite monochromator | θmax = 30.0°, θmin = 3.0° |
ω–scan | h = −15→15 |
Absorption correction: numerical X-RED (Stoe & Cie, 1996b) | k = −9→0 |
Tmin = 0.801, Tmax = 0.888 | l = 0→16 |
2776 measured reflections | 3 standard reflections every 60 min |
1388 independent reflections | intensity decay: 1.0% |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0895P)2] where P = (Fo2 + 2Fc2)/3 |
1388 reflections | (Δ/σ)max < 0.001 |
78 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.70308 (5) | 0.0000 | 0.11959 (5) | 0.0599 (3) | |
O1W | 0.43032 (18) | 0.0000 | 0.13863 (17) | 0.0822 (9) | |
H1W | 0.4015 (12) | 0.0000 | 0.070 (3) | 0.090 (14)* | |
H2W | 0.495 (3) | 0.0000 | 0.1464 (3) | 0.086 (13)* | |
N5 | 0.01901 (14) | 0.0000 | 0.38809 (14) | 0.0343 (4) | |
O2' | 0.35773 (15) | 0.0000 | 0.32597 (15) | 0.0652 (6) | |
H2' | 0.3673 (5) | 0.0000 | 0.262 (3) | 0.060 (9)* | |
C13 | 0.11818 (16) | 0.0000 | 0.47604 (16) | 0.0344 (4) | |
C6 | −0.10741 (17) | 0.0000 | 0.40238 (17) | 0.0424 (5) | |
H6A | −0.1494 | −0.1140 | 0.3639 | 0.051* | 0.50 |
C1 | 0.23454 (18) | 0.0000 | 0.45637 (18) | 0.0429 (5) | |
C1' | 0.34721 (19) | 0.0000 | 0.5551 (2) | 0.0578 (7) | |
H1'1 | 0.4191 | 0.0000 | 0.5253 | 0.087* | |
H1'2 | 0.3472 | −0.1142 | 0.6015 | 0.087* | 0.50 |
C2 | 0.24504 (19) | 0.0000 | 0.34112 (19) | 0.0488 (6) | |
C4 | 0.02755 (19) | 0.0000 | 0.27661 (18) | 0.0426 (5) | |
H4 | −0.0436 | 0.0000 | 0.2174 | 0.051* | |
C3' | 0.1451 (2) | 0.0000 | 0.1251 (2) | 0.0682 (9) | |
H3'1 | 0.2292 | 0.0000 | 0.1209 | 0.102* | |
H3'2 | 0.1049 | 0.1142 | 0.0875 | 0.102* | 0.50 |
C3 | 0.1392 (2) | 0.0000 | 0.25002 (18) | 0.0481 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0415 (4) | 0.0965 (6) | 0.0401 (4) | 0.000 | 0.0067 (2) | 0.000 |
O1W | 0.0398 (9) | 0.174 (3) | 0.0367 (9) | 0.000 | 0.0161 (7) | 0.000 |
N5 | 0.0242 (7) | 0.0509 (9) | 0.0276 (7) | 0.000 | 0.0062 (5) | 0.000 |
O2' | 0.0291 (7) | 0.1341 (18) | 0.0354 (9) | 0.000 | 0.0134 (6) | 0.000 |
C13 | 0.0255 (8) | 0.0505 (10) | 0.0277 (8) | 0.000 | 0.0072 (6) | 0.000 |
C6 | 0.0230 (8) | 0.0761 (14) | 0.0277 (9) | 0.000 | 0.0055 (7) | 0.000 |
C1 | 0.0246 (8) | 0.0752 (14) | 0.0284 (9) | 0.000 | 0.0052 (7) | 0.000 |
C1' | 0.0238 (8) | 0.115 (2) | 0.0329 (10) | 0.000 | 0.0043 (7) | 0.000 |
C2 | 0.0270 (9) | 0.0885 (17) | 0.0318 (10) | 0.000 | 0.0091 (7) | 0.000 |
C4 | 0.0299 (8) | 0.0692 (14) | 0.0279 (8) | 0.000 | 0.0058 (7) | 0.000 |
C3' | 0.0393 (11) | 0.136 (3) | 0.0297 (10) | 0.000 | 0.0099 (9) | 0.000 |
C3 | 0.0314 (9) | 0.0851 (16) | 0.0280 (9) | 0.000 | 0.0074 (7) | 0.000 |
Geometric parameters (Å, º) top
O1W—H1W | 0.81 (3) | C1—C2 | 1.411 (3) |
O1W—H2W | 0.71 (3) | C1—C1' | 1.506 (3) |
N5—C13 | 1.333 (3) | C1'—H1'1 | 0.96 |
N5—C4 | 1.359 (3) | C1'—H1'2 | 0.96 |
N5—C6 | 1.474 (3) | C1'—H1'3 | 0.96 |
O2'—C2 | 1.324 (3) | C2—C3 | 1.403 (3) |
O2'—H2' | 0.80 (3) | C4—C3 | 1.370 (3) |
C13—C1 | 1.386 (3) | C4—H4 | 0.93 |
C13—C6i | 1.488 (3) | C3'—C3 | 1.510 (3) |
C6—C13i | 1.488 (3) | C3'—H3'1 | 0.96 |
C6—H6A | 0.97 | C3'—H3'2 | 0.96 |
C6—H6B | 0.97 | C3'—H3'3 | 0.96 |
| | | |
H1W—O1W—H2W | 106.3 | H1'1—C1'—H1'2 | 109.5 |
C13—N5—C4 | 121.8 (2) | C1—C1'—H1'3 | 109.5 |
C13—N5—C6 | 123.7 (2) | H1'1—C1'—H1'3 | 109.5 |
C4—N5—C6 | 114.5 (2) | H1'2—C1'—H1'3 | 109.5 |
C2—O2'—H2' | 119.3 | O2'—C2—C3 | 123.6 (2) |
N5—C13—C1 | 120.7 (2) | O2'—C2—C1 | 116.4 (2) |
N5—C13—C6i | 121.2 (2) | C3—C2—C1 | 120.0 (2) |
C1—C13—C6i | 118.2 (2) | N5—C4—C3 | 121.1 (2) |
N5—C6—C13i | 115.1 (2) | N5—C4—H4 | 119.5 |
N5—C6—H6A | 108.5 | C3—C4—H4 | 119.5 |
C13i—C6—H6A | 108.5 | C3—C3'—H3'1 | 109.5 |
N5—C6—H6B | 108.5 | C3—C3'—H3'2 | 109.5 |
C13i—C6—H6B | 108.5 | H3'1—C3'—H3'2 | 109.5 |
H6A—C6—H6B | 107.5 | C3—C3'—H3'3 | 109.5 |
C13—C1—C2 | 118.3 (2) | H3'1—C3'—H3'3 | 109.5 |
C13—C1—C1' | 121.1 (2) | H3'2—C3'—H3'3 | 109.5 |
C2—C1—C1' | 120.6 (2) | C4—C3—C2 | 118.2 (2) |
C1—C1'—H1'1 | 109.5 | C4—C3—C3' | 119.6 (2) |
C1—C1'—H1'2 | 109.5 | C2—C3—C3' | 122.2 (2) |
| | | |
C4—N5—C13—C1 | 0.0 | C1'—C1—C2—O2' | 0.0 |
C6—N5—C13—C1 | 180.0 | C13—C1—C2—C3 | 0.0 |
C4—N5—C13—C6i | 180.0 | C1'—C1—C2—C3 | 180.0 |
C6—N5—C13—C6i | 0.0 | C13—N5—C4—C3 | 0.0 |
C13—N5—C6—C13i | 0.0 | C6—N5—C4—C3 | 180.0 |
C4—N5—C6—C13i | 180.0 | N5—C4—C3—C2 | 0.0 |
N5—C13—C1—C2 | 0.0 | N5—C4—C3—C3' | 180.0 |
C6i—C13—C1—C2 | 180.0 | O2'—C2—C3—C4 | 180.0 |
N5—C13—C1—C1' | 180.0 | C1—C2—C3—C4 | 0.0 |
C6i—C13—C1—C1' | 0.0 | O2'—C2—C3—C3' | 0.0 |
C13—C1—C2—O2' | 180.0 | C1—C2—C3—C3' | 180.0 |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2′—H2′···O1W | 0.80 (3) | 1.79 (3) | 2.564 (4) | 165 (2) |
O1W—H2W···Cl1 | 0.71 (3) | 2.44 (3) | 3.133 (5) | 165 (4) |
O1W—H1W···Cl1ii | 0.81 (3) | 2.28 (3) | 3.085 (5) | 173 (2) |
C4—H4···Cl1iii | 0.93 | 2.81 | 3.675 (5) | 156 |
C6—H6A···Cl1iv | 0.97 | 2.74 | 3.588 (5) | 147 |
Symmetry codes: (ii) −x+1, y, −z; (iii) x−1, y, z; (iv) −x+1/2, y−1/2, −z+1/2. |
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