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The doubly protonated terpyridinium cation in the title compound, C15H13N32+·2NO3-, has a cis-cis conformation. Both H atoms attached to the N atoms of the outer rings form hydrogen bonds with the same O atom of one of the two nitrate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009931/at6002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009931/at6002Isup2.hkl
Contains datablock I

CCDC reference: 271807

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.101
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL package (Otwinowski & Minor, 1997); data reduction: HKL package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2,2':6',2''-Terpyridinium nitrate top
Crystal data top
C15H13N32+·2NO3F(000) = 744
Mr = 359.30Dx = 1.538 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7697 reflections
a = 11.9992 (4) Åθ = 1.7–26.4°
b = 7.8052 (2) ŵ = 0.12 mm1
c = 16.6679 (3) ÅT = 123 K
β = 96.158 (2)°Fragment, yellow
V = 1552.04 (7) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 26.4°, θmin = 1.7°
φ and ω scans to cover a quadrant of the reciprocal spaceh = 1414
7697 measured reflectionsk = 99
3140 independent reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.9364P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3140 reflectionsΔρmax = 0.55 e Å3
288 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (4)
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
C20.04607 (13)0.3527 (2)0.30219 (9)0.0269 (3)
H20.0671 (14)0.396 (2)0.2527 (11)0.029 (4)*
C30.04486 (13)0.2489 (2)0.30964 (9)0.0273 (3)
H30.0952 (15)0.220 (2)0.2623 (11)0.034 (5)*
C40.06354 (13)0.1931 (2)0.38589 (9)0.0275 (3)
H40.1264 (15)0.124 (2)0.3921 (10)0.032 (5)*
C50.00730 (12)0.24451 (19)0.45289 (9)0.0249 (3)
H50.0072 (15)0.209 (2)0.5056 (12)0.037 (5)*
C60.09689 (12)0.35107 (18)0.44344 (8)0.0211 (3)
C70.17546 (11)0.41757 (17)0.51096 (8)0.0205 (3)
C80.16127 (12)0.37838 (19)0.59115 (8)0.0241 (3)
H80.1023 (15)0.307 (2)0.6043 (10)0.029 (4)*
C90.23521 (13)0.4480 (2)0.65155 (9)0.0271 (3)
H90.2261 (15)0.425 (2)0.7074 (11)0.038 (5)*
C100.32131 (12)0.5515 (2)0.63134 (9)0.0250 (3)
H100.3730 (15)0.602 (2)0.6710 (11)0.027 (4)*
C110.33129 (12)0.58048 (18)0.54965 (8)0.0211 (3)
C130.42573 (12)0.68091 (18)0.52339 (8)0.0220 (3)
C140.51433 (12)0.74482 (19)0.57505 (9)0.0251 (3)
H140.5177 (15)0.728 (2)0.6315 (11)0.031 (4)*
C150.60108 (13)0.83188 (19)0.54394 (9)0.0269 (3)
H150.6603 (15)0.874 (2)0.5782 (11)0.034 (5)*
C160.59899 (13)0.85569 (19)0.46157 (9)0.0264 (3)
H160.6538 (15)0.917 (2)0.4377 (11)0.032 (5)*
C170.50987 (13)0.79050 (19)0.41170 (9)0.0263 (3)
H170.5008 (15)0.799 (2)0.3547 (11)0.030 (4)*
N10.11343 (11)0.40072 (16)0.36783 (7)0.0233 (3)
H10.1719 (16)0.471 (3)0.3622 (11)0.038 (5)*
N20.33269 (11)0.53262 (17)0.25378 (7)0.0284 (3)
N30.15422 (10)0.59074 (16)0.89273 (7)0.0253 (3)
N120.25915 (10)0.51589 (15)0.49035 (7)0.0203 (3)
N180.42728 (10)0.70595 (16)0.44321 (7)0.0234 (3)
H180.3709 (17)0.662 (3)0.4078 (12)0.043 (5)*
O10.27393 (11)0.45214 (19)0.20153 (7)0.0482 (4)
O20.43353 (10)0.5608 (2)0.24961 (8)0.0494 (4)
O30.28627 (10)0.59395 (17)0.31308 (7)0.0385 (3)
O40.19175 (11)0.50052 (18)0.84010 (7)0.0463 (4)
O50.07205 (9)0.68760 (17)0.87367 (6)0.0375 (3)
O60.19563 (9)0.58065 (16)0.96424 (6)0.0350 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0324 (8)0.0283 (8)0.0195 (7)0.0019 (6)0.0010 (6)0.0009 (6)
C30.0295 (8)0.0271 (8)0.0241 (7)0.0016 (6)0.0023 (6)0.0025 (6)
C40.0257 (8)0.0279 (8)0.0286 (8)0.0052 (6)0.0017 (6)0.0002 (6)
C50.0253 (7)0.0273 (7)0.0222 (7)0.0025 (6)0.0028 (6)0.0026 (6)
C60.0223 (7)0.0208 (7)0.0203 (7)0.0021 (6)0.0035 (5)0.0002 (5)
C70.0200 (7)0.0203 (7)0.0215 (7)0.0017 (5)0.0036 (5)0.0000 (5)
C80.0229 (7)0.0280 (8)0.0222 (7)0.0020 (6)0.0055 (5)0.0014 (6)
C90.0280 (8)0.0345 (8)0.0192 (7)0.0003 (6)0.0047 (6)0.0001 (6)
C100.0237 (7)0.0298 (8)0.0210 (7)0.0012 (6)0.0007 (6)0.0033 (6)
C110.0209 (7)0.0198 (7)0.0228 (7)0.0016 (5)0.0031 (5)0.0012 (5)
C130.0226 (7)0.0195 (7)0.0241 (7)0.0019 (5)0.0043 (5)0.0015 (5)
C140.0238 (7)0.0252 (7)0.0260 (7)0.0008 (6)0.0016 (6)0.0016 (6)
C150.0218 (7)0.0243 (7)0.0340 (8)0.0001 (6)0.0005 (6)0.0034 (6)
C160.0226 (7)0.0215 (7)0.0364 (8)0.0004 (6)0.0086 (6)0.0004 (6)
C170.0275 (8)0.0239 (7)0.0286 (8)0.0003 (6)0.0079 (6)0.0004 (6)
N10.0253 (6)0.0238 (6)0.0212 (6)0.0036 (5)0.0038 (5)0.0004 (5)
N20.0293 (7)0.0336 (7)0.0223 (6)0.0011 (6)0.0032 (5)0.0020 (5)
N30.0236 (6)0.0300 (7)0.0224 (6)0.0040 (5)0.0023 (5)0.0004 (5)
N120.0203 (6)0.0200 (6)0.0207 (6)0.0006 (5)0.0026 (4)0.0008 (4)
N180.0228 (6)0.0232 (6)0.0243 (6)0.0012 (5)0.0031 (5)0.0011 (5)
O10.0449 (7)0.0632 (9)0.0361 (7)0.0065 (7)0.0027 (6)0.0204 (6)
O20.0299 (7)0.0734 (10)0.0469 (8)0.0044 (6)0.0128 (5)0.0105 (7)
O30.0346 (6)0.0565 (8)0.0255 (6)0.0109 (6)0.0087 (5)0.0082 (5)
O40.0527 (8)0.0596 (9)0.0269 (6)0.0249 (7)0.0059 (5)0.0074 (6)
O50.0334 (6)0.0519 (8)0.0273 (6)0.0204 (6)0.0033 (5)0.0049 (5)
O60.0331 (6)0.0468 (7)0.0238 (6)0.0132 (5)0.0032 (4)0.0056 (5)
Geometric parameters (Å, º) top
C2—N11.3421 (19)C11—C131.482 (2)
C2—C31.375 (2)C13—N181.3527 (18)
C2—H20.950 (18)C13—C141.387 (2)
C3—C41.384 (2)C14—C151.389 (2)
C3—H30.966 (19)C14—H140.946 (18)
C4—C51.388 (2)C15—C161.383 (2)
C4—H40.942 (19)C15—H150.925 (19)
C5—C61.382 (2)C16—C171.379 (2)
C5—H50.955 (19)C16—H160.934 (19)
C6—N11.3533 (18)C17—N181.3437 (19)
C6—C71.4823 (19)C17—H170.947 (18)
C7—N121.3378 (18)N1—H10.90 (2)
C7—C81.3992 (19)N2—O11.2323 (18)
C8—C91.380 (2)N2—O21.2391 (18)
C8—H80.946 (19)N2—O31.2784 (17)
C9—C101.381 (2)N3—O61.2437 (16)
C9—H90.966 (19)N3—O41.2461 (17)
C10—C111.3981 (19)N3—O51.2559 (16)
C10—H100.941 (18)N18—H180.92 (2)
C11—N121.3404 (18)
N1—C2—C3120.34 (14)C10—C11—C13121.42 (13)
N1—C2—H2114.6 (11)N18—C13—C14118.07 (13)
C3—C2—H2125.0 (11)N18—C13—C11117.39 (12)
C2—C3—C4118.45 (14)C14—C13—C11124.49 (13)
C2—C3—H3119.6 (11)C13—C14—C15119.95 (14)
C4—C3—H3121.9 (11)C13—C14—H14121.1 (11)
C3—C4—C5120.15 (14)C15—C14—H14118.9 (11)
C3—C4—H4119.5 (11)C16—C15—C14120.11 (14)
C5—C4—H4120.3 (11)C16—C15—H15119.7 (11)
C6—C5—C4119.94 (13)C14—C15—H15120.2 (11)
C6—C5—H5120.1 (11)C17—C16—C15118.63 (14)
C4—C5—H5119.9 (11)C17—C16—H16117.9 (11)
N1—C6—C5118.18 (13)C15—C16—H16123.5 (11)
N1—C6—C7117.52 (12)N18—C17—C16120.14 (14)
C5—C6—C7124.30 (12)N18—C17—H17114.5 (11)
N12—C7—C8122.85 (13)C16—C17—H17125.3 (11)
N12—C7—C6116.08 (12)C2—N1—C6122.93 (13)
C8—C7—C6121.07 (13)C2—N1—H1119.5 (12)
C9—C8—C7118.43 (14)C6—N1—H1117.6 (12)
C9—C8—H8120.2 (10)O1—N2—O2122.62 (13)
C7—C8—H8121.4 (10)O1—N2—O3118.26 (13)
C8—C9—C10119.44 (13)O2—N2—O3119.07 (13)
C8—C9—H9119.9 (11)O6—N3—O4120.09 (13)
C10—C9—H9120.6 (11)O6—N3—O5120.17 (12)
C9—C10—C11118.46 (13)O4—N3—O5119.69 (13)
C9—C10—H10121.7 (10)C7—N12—C11118.00 (12)
C11—C10—H10119.8 (11)C17—N18—C13123.10 (13)
N12—C11—C10122.77 (13)C17—N18—H18117.2 (12)
N12—C11—C13115.78 (12)C13—N18—H18119.7 (12)
N1—C2—C3—C41.2 (2)N12—C11—C13—C14173.91 (13)
C2—C3—C4—C51.2 (2)C10—C11—C13—C144.1 (2)
C3—C4—C5—C60.2 (2)N18—C13—C14—C150.1 (2)
C4—C5—C6—N10.8 (2)C11—C13—C14—C15177.50 (13)
C4—C5—C6—C7178.10 (14)C13—C14—C15—C160.3 (2)
N1—C6—C7—N122.72 (19)C14—C15—C16—C170.4 (2)
C5—C6—C7—N12178.39 (13)C15—C16—C17—N180.0 (2)
N1—C6—C7—C8177.21 (13)C3—C2—N1—C60.2 (2)
C5—C6—C7—C81.7 (2)C5—C6—N1—C20.8 (2)
N12—C7—C8—C91.8 (2)C7—C6—N1—C2178.16 (13)
C6—C7—C8—C9178.16 (13)C8—C7—N12—C110.8 (2)
C7—C8—C9—C100.9 (2)C6—C7—N12—C11179.16 (12)
C8—C9—C10—C110.8 (2)C10—C11—N12—C71.1 (2)
C9—C10—C11—N121.8 (2)C13—C11—N12—C7176.93 (12)
C9—C10—C11—C13176.06 (13)C16—C17—N18—C130.4 (2)
N12—C11—C13—N183.48 (19)C14—C13—N18—C170.5 (2)
C10—C11—C13—N18178.50 (13)C11—C13—N18—C17178.07 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.90 (2)1.93 (2)2.796 (2)160 (2)
N18—H18···O30.92 (2)1.86 (2)2.747 (2)162 (2)
 

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