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The title compound is a salt, trans-1,1′-dihydr­oxy-4,4′-diazene­diyldipyridinium dichloride, C10H10N4O22+·2C l, in which the trans-4,4′-azopyridine N,N′-dioxide cation is located on an inversion centre with the pyridine N-oxide atoms protonated. The Cl anions form strong hydrogen bonds to these H atoms. Weak C—H...Cl hydrogen bonds link the cations and anions into a two-dimensional sheet.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006630/sj2220sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006630/sj2220Isup2.hkl
Contains datablock I

CCDC reference: 640494

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.051
  • wR factor = 0.126
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. CL1 .. 2.89 Ang. PLAT731_ALERT_1_C Bond Calc 0.98(4), Rep 0.975(19) ...... 2.11 su-Ra O1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.98(4), Rep 0.975(19) ...... 2.11 su-Ra O1 -H1 1.555 1.555 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.27 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.941 Tmax scaled 0.910 Tmin scaled 0.867
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXTL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXTL97; molecular graphics: SHELXTL97; software used to prepare material for publication: SHELXTL97.

trans-1,1'-Dihydroxy-4,4'-diazenediyldipyridinium dichloride top
Crystal data top
C10H10N4O22+·2ClF(000) = 296
Mr = 289.12Dx = 1.546 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6026 reflections
a = 5.2681 (8) Åθ = 2.7–27.0°
b = 12.9203 (18) ŵ = 0.52 mm1
c = 9.2022 (14) ÅT = 298 K
β = 97.520 (6)°Block, red
V = 620.96 (16) Å30.30 × 0.22 × 0.18 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1359 independent reflections
Radiation source: fine-focus sealed tube1213 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
φ and ω scansθmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.921, Tmax = 0.967k = 1616
6026 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051All H-atom parameters refined
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.3949P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1359 reflectionsΔρmax = 0.36 e Å3
113 parametersΔρmin = 0.34 e Å3
2 restraintsExtinction correction: SHELXTL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.076 (9)
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*/UeqOcc. (<1)
Cl10.53099 (13)0.38193 (5)0.17407 (7)0.0585 (3)
O10.3808 (4)0.25684 (14)0.0478 (2)0.0621 (5)
N10.2984 (3)0.31897 (13)0.15213 (18)0.0406 (4)
N20.1161 (15)0.4893 (6)0.5000 (15)0.037 (2)0.56 (4)
C10.0853 (5)0.37463 (18)0.1197 (3)0.0492 (6)
C20.0012 (5)0.4317 (2)0.2281 (3)0.0584 (7)
C30.1374 (6)0.42990 (18)0.3674 (3)0.0616 (8)
C40.3554 (6)0.37193 (18)0.3953 (3)0.0564 (7)
C50.4337 (5)0.31570 (19)0.2857 (3)0.0473 (5)
H10.443 (9)0.297 (3)0.030 (4)0.142 (18)*
H4A0.453 (5)0.364 (2)0.499 (2)0.058 (8)*
H2A0.145 (5)0.471 (2)0.202 (3)0.054 (7)*
H1A0.007 (7)0.371 (2)0.022 (4)0.073 (9)*
H5A0.596 (6)0.274 (3)0.297 (3)0.073 (9)*
N2'0.068 (3)0.4887 (11)0.445 (2)0.052 (3)0.44 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0679 (5)0.0567 (4)0.0548 (4)0.0142 (3)0.0232 (3)0.0107 (2)
O10.0915 (14)0.0495 (9)0.0513 (10)0.0046 (9)0.0317 (9)0.0043 (8)
N10.0470 (10)0.0393 (9)0.0373 (8)0.0025 (7)0.0125 (7)0.0003 (7)
N20.040 (3)0.037 (2)0.034 (4)0.0004 (15)0.008 (2)0.006 (2)
C10.0493 (13)0.0459 (12)0.0509 (13)0.0016 (9)0.0015 (10)0.0050 (9)
C20.0556 (15)0.0424 (12)0.0828 (18)0.0068 (11)0.0299 (13)0.0108 (12)
C30.101 (2)0.0365 (11)0.0569 (14)0.0122 (13)0.0461 (15)0.0041 (10)
C40.0846 (19)0.0444 (12)0.0406 (12)0.0172 (12)0.0100 (12)0.0002 (9)
C50.0468 (12)0.0491 (12)0.0460 (11)0.0079 (10)0.0058 (9)0.0064 (9)
N2'0.060 (5)0.054 (3)0.044 (6)0.001 (3)0.006 (5)0.003 (4)
Geometric parameters (Å, º) top
O1—N11.365 (2)C2—C31.390 (4)
O1—H10.975 (19)C2—H2A0.91 (3)
N1—C11.334 (3)C3—C41.367 (4)
N1—C51.338 (3)C3—N2'1.57 (3)
N2—N2'i0.658 (13)C4—C51.351 (4)
N2—N2'1.035 (6)C4—H4A1.024 (17)
N2—N2i1.25 (2)C5—H5A1.01 (3)
N2—C31.458 (16)N2'—N2i0.658 (13)
C1—C21.366 (4)N2'—N2'i1.20 (3)
C1—H1A0.94 (3)
N1—O1—H1112 (3)C1—C2—H2A116.9 (17)
C1—N1—C5123.6 (2)C3—C2—H2A124.5 (17)
C1—N1—O1119.70 (19)C4—C3—C2120.6 (2)
C5—N1—O1116.6 (2)C4—C3—N2106.6 (3)
N2'i—N2—N2'87 (3)C2—C3—N2132.4 (3)
N2'i—N2—N2i55.5 (15)C4—C3—N2'142.5 (5)
N2'i—N2—C3161.6 (13)C2—C3—N2'95.8 (5)
N2'—N2—C376 (2)C5—C4—C3119.1 (2)
N2i—N2—C3107.3 (12)C5—C4—H4A118.3 (16)
N1—C1—C2118.6 (2)C3—C4—H4A122.4 (16)
N1—C1—H1A116 (2)N1—C5—C4119.4 (2)
C2—C1—H1A125 (2)N1—C5—H5A116.9 (18)
C1—C2—C3118.6 (2)C4—C5—H5A123.6 (18)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl10.98 (2)1.83 (2)2.7979 (19)174 (5)
C2—H2A···Cl1ii0.91 (3)2.77 (3)3.671 (3)167 (2)
C1—H1A···Cl1iii0.94 (3)2.89 (4)3.712 (3)146 (3)
Symmetry codes: (ii) x, y+1, z; (iii) x1, y, z.
 

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