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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. C16H20N2O22+·2Cl·2H2O. 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008313/na1479sup1.cif
Contains datablocks NPO, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008313/na1479Isup2.hkl
Contains datablock I

CCDC reference: 150854

Computing details top

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·2H2OF(000) = 400
Mr = 379.28Dx = 1.407 Mg m3
Monoclinic, I2/mMo Kα radiation, λ = 0.71073 Å
a = 11.255 (15) ÅCell parameters from 10 reflections
b = 6.8650 (13) Åθ = 6.4–14.3°
c = 11.9530 (12) ŵ = 0.39 mm1
β = 104.15 (2)°T = 293 K
V = 895.5 (12) Å3Prism, colourless
Z = 20.50 × 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 tubeRint = 0.021
Graphite monochromatorθmax = 30.0°, θmin = 3.0°
ω–scanh = 1515
Absorption correction: numerical
X-RED (Stoe & Cie, 1996b)
k = 90
Tmin = 0.801, Tmax = 0.888l = 016
2776 measured reflections3 standard reflections every 60 min
1388 independent reflections intensity decay: 1.0%
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H 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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.33 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.70308 (5)0.00000.11959 (5)0.0599 (3)
O1W0.43032 (18)0.00000.13863 (17)0.0822 (9)
H1W0.4015 (12)0.00000.070 (3)0.090 (14)*
H2W0.495 (3)0.00000.1464 (3)0.086 (13)*
N50.01901 (14)0.00000.38809 (14)0.0343 (4)
O2'0.35773 (15)0.00000.32597 (15)0.0652 (6)
H2'0.3673 (5)0.00000.262 (3)0.060 (9)*
C130.11818 (16)0.00000.47604 (16)0.0344 (4)
C60.10741 (17)0.00000.40238 (17)0.0424 (5)
H6A0.14940.11400.36390.051*0.50
C10.23454 (18)0.00000.45637 (18)0.0429 (5)
C1'0.34721 (19)0.00000.5551 (2)0.0578 (7)
H1'10.41910.00000.52530.087*
H1'20.34720.11420.60150.087*0.50
C20.24504 (19)0.00000.34112 (19)0.0488 (6)
C40.02755 (19)0.00000.27661 (18)0.0426 (5)
H40.04360.00000.21740.051*
C3'0.1451 (2)0.00000.1251 (2)0.0682 (9)
H3'10.22920.00000.12090.102*
H3'20.10490.11420.08750.102*0.50
C30.1392 (2)0.00000.25002 (18)0.0481 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0415 (4)0.0965 (6)0.0401 (4)0.0000.0067 (2)0.000
O1W0.0398 (9)0.174 (3)0.0367 (9)0.0000.0161 (7)0.000
N50.0242 (7)0.0509 (9)0.0276 (7)0.0000.0062 (5)0.000
O2'0.0291 (7)0.1341 (18)0.0354 (9)0.0000.0134 (6)0.000
C130.0255 (8)0.0505 (10)0.0277 (8)0.0000.0072 (6)0.000
C60.0230 (8)0.0761 (14)0.0277 (9)0.0000.0055 (7)0.000
C10.0246 (8)0.0752 (14)0.0284 (9)0.0000.0052 (7)0.000
C1'0.0238 (8)0.115 (2)0.0329 (10)0.0000.0043 (7)0.000
C20.0270 (9)0.0885 (17)0.0318 (10)0.0000.0091 (7)0.000
C40.0299 (8)0.0692 (14)0.0279 (8)0.0000.0058 (7)0.000
C3'0.0393 (11)0.136 (3)0.0297 (10)0.0000.0099 (9)0.000
C30.0314 (9)0.0851 (16)0.0280 (9)0.0000.0074 (7)0.000
Geometric parameters (Å, º) top
O1W—H1W0.81 (3)C1—C21.411 (3)
O1W—H2W0.71 (3)C1—C1'1.506 (3)
N5—C131.333 (3)C1'—H1'10.96
N5—C41.359 (3)C1'—H1'20.96
N5—C61.474 (3)C1'—H1'30.96
O2'—C21.324 (3)C2—C31.403 (3)
O2'—H2'0.80 (3)C4—C31.370 (3)
C13—C11.386 (3)C4—H40.93
C13—C6i1.488 (3)C3'—C31.510 (3)
C6—C13i1.488 (3)C3'—H3'10.96
C6—H6A0.97C3'—H3'20.96
C6—H6B0.97C3'—H3'30.96
H1W—O1W—H2W106.3H1'1—C1'—H1'2109.5
C13—N5—C4121.8 (2)C1—C1'—H1'3109.5
C13—N5—C6123.7 (2)H1'1—C1'—H1'3109.5
C4—N5—C6114.5 (2)H1'2—C1'—H1'3109.5
C2—O2'—H2'119.3O2'—C2—C3123.6 (2)
N5—C13—C1120.7 (2)O2'—C2—C1116.4 (2)
N5—C13—C6i121.2 (2)C3—C2—C1120.0 (2)
C1—C13—C6i118.2 (2)N5—C4—C3121.1 (2)
N5—C6—C13i115.1 (2)N5—C4—H4119.5
N5—C6—H6A108.5C3—C4—H4119.5
C13i—C6—H6A108.5C3—C3'—H3'1109.5
N5—C6—H6B108.5C3—C3'—H3'2109.5
C13i—C6—H6B108.5H3'1—C3'—H3'2109.5
H6A—C6—H6B107.5C3—C3'—H3'3109.5
C13—C1—C2118.3 (2)H3'1—C3'—H3'3109.5
C13—C1—C1'121.1 (2)H3'2—C3'—H3'3109.5
C2—C1—C1'120.6 (2)C4—C3—C2118.2 (2)
C1—C1'—H1'1109.5C4—C3—C3'119.6 (2)
C1—C1'—H1'2109.5C2—C3—C3'122.2 (2)
C4—N5—C13—C10.0C1'—C1—C2—O2'0.0
C6—N5—C13—C1180.0C13—C1—C2—C30.0
C4—N5—C13—C6i180.0C1'—C1—C2—C3180.0
C6—N5—C13—C6i0.0C13—N5—C4—C30.0
C13—N5—C6—C13i0.0C6—N5—C4—C3180.0
C4—N5—C6—C13i180.0N5—C4—C3—C20.0
N5—C13—C1—C20.0N5—C4—C3—C3'180.0
C6i—C13—C1—C2180.0O2'—C2—C3—C4180.0
N5—C13—C1—C1'180.0C1—C2—C3—C40.0
C6i—C13—C1—C1'0.0O2'—C2—C3—C3'0.0
C13—C1—C2—O2'180.0C1—C2—C3—C3'180.0
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1W0.80 (3)1.79 (3)2.564 (4)165 (2)
O1W—H2W···Cl10.71 (3)2.44 (3)3.133 (5)165 (4)
O1W—H1W···Cl1ii0.81 (3)2.28 (3)3.085 (5)173 (2)
C4—H4···Cl1iii0.932.813.675 (5)156
C6—H6A···Cl1iv0.972.743.588 (5)147
Symmetry codes: (ii) x+1, y, z; (iii) x1, y, z; (iv) x+1/2, y1/2, z+1/2.
 

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