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In the title salt, C10H10N3+·C8H5O4, the protonated 4,4′-dipyridylamine and deprotonated isophthalic acid mol­ecules are bound together in the crystal structure through π–π stacking, O...H—N, O...H—C and N...H—O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503463X/sj6139sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503463X/sj6139Isup2.hkl
Contains datablock I

CCDC reference: 289891

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.101
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O4 .. C10 .. 2.90 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.20
0 ALERT level A = In general: serious problem 1 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: XCIF (Bruker, 2001).

4-(4-Pyridylamino)pyridinium isophthalate top
Crystal data top
C10N3H10+·C8H5O4F(000) = 704
Mr = 337.33Dx = 1.431 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 936 reflections
a = 9.3246 (18) Åθ = 2.7–27.9°
b = 15.134 (3) ŵ = 0.10 mm1
c = 11.655 (2) ÅT = 150 K
β = 107.787 (3)°Irregular polygon, light yellow
V = 1566.1 (5) Å30.34 × 0.31 × 0.25 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
3742 independent reflections
Radiation source: fine-focus sealed tube3246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick 1996)
h = 1212
Tmin = 0.900, Tmax = 0.98k = 1919
15761 measured reflectionsl = 1515
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.7162P]
where P = (Fo2 + 2Fc2)/3
3742 reflections(Δ/σ)max < 0.001
227 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Experimental. In a thin film of perfluropolyether oil on a mohair fibre

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
O10.34974 (10)0.11099 (5)0.41885 (8)0.02368 (19)
O20.19178 (10)0.10254 (6)0.52802 (8)0.0259 (2)
O30.63653 (11)0.39044 (6)0.44486 (8)0.0295 (2)
H3A0.68940.42850.42410.044*
O40.67686 (11)0.47818 (6)0.60559 (9)0.0320 (2)
N10.20141 (12)0.48577 (7)0.62266 (10)0.0246 (2)
N20.23674 (11)0.05480 (6)0.62987 (9)0.0222 (2)
H2A0.27140.00110.60960.027*
N30.08474 (11)0.30872 (6)0.72439 (9)0.0211 (2)
H3B0.12060.33130.77960.025*
C10.18105 (14)0.48763 (8)0.73191 (11)0.0247 (3)
H10.23270.53140.78780.030*
C20.08894 (14)0.42925 (8)0.76701 (11)0.0230 (2)
H2B0.07800.43320.84520.028*
C30.01176 (12)0.36414 (7)0.68646 (10)0.0196 (2)
C40.03145 (13)0.36225 (8)0.57240 (11)0.0228 (2)
H40.01950.31980.51420.027*
C50.12717 (14)0.42383 (8)0.54597 (11)0.0242 (2)
H50.14060.42170.46840.029*
C60.12665 (14)0.08682 (8)0.58937 (11)0.0234 (2)
H60.08590.05040.54070.028*
C70.07177 (13)0.17079 (8)0.61657 (10)0.0219 (2)
H70.00600.19230.58700.026*
C80.13196 (12)0.22486 (7)0.68888 (10)0.0186 (2)
C90.24476 (13)0.18829 (7)0.73203 (10)0.0198 (2)
H90.28630.22230.78270.024*
C100.29427 (13)0.10423 (8)0.70116 (10)0.0213 (2)
H100.37050.08020.73040.026*
C110.46110 (12)0.27514 (7)0.52942 (10)0.0192 (2)
H110.47800.26270.45470.023*
C120.52574 (13)0.34998 (7)0.59467 (10)0.0204 (2)
C130.50560 (13)0.36639 (8)0.70637 (11)0.0233 (2)
H130.54990.41710.75130.028*
C140.42108 (14)0.30888 (8)0.75221 (11)0.0236 (2)
H140.41010.31930.82950.028*
C150.35235 (13)0.23600 (8)0.68506 (10)0.0214 (2)
H150.29170.19780.71560.026*
C160.37188 (12)0.21845 (7)0.57293 (10)0.0184 (2)
C170.61995 (13)0.41295 (8)0.54945 (11)0.0228 (2)
C180.29773 (13)0.13812 (7)0.50157 (10)0.0185 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0317 (5)0.0182 (4)0.0260 (4)0.0050 (3)0.0160 (4)0.0032 (3)
O20.0282 (4)0.0241 (4)0.0297 (5)0.0075 (3)0.0151 (4)0.0037 (3)
O30.0371 (5)0.0242 (4)0.0317 (5)0.0125 (4)0.0172 (4)0.0036 (4)
O40.0389 (5)0.0244 (5)0.0332 (5)0.0126 (4)0.0115 (4)0.0052 (4)
N10.0248 (5)0.0197 (5)0.0305 (5)0.0016 (4)0.0104 (4)0.0026 (4)
N20.0261 (5)0.0149 (4)0.0245 (5)0.0022 (4)0.0062 (4)0.0003 (4)
N30.0257 (5)0.0169 (5)0.0247 (5)0.0021 (4)0.0138 (4)0.0029 (4)
C10.0254 (6)0.0190 (6)0.0303 (6)0.0018 (5)0.0092 (5)0.0036 (5)
C20.0258 (6)0.0201 (6)0.0250 (6)0.0002 (4)0.0107 (5)0.0025 (4)
C30.0198 (5)0.0157 (5)0.0253 (6)0.0014 (4)0.0098 (4)0.0013 (4)
C40.0260 (6)0.0196 (5)0.0231 (6)0.0016 (4)0.0079 (5)0.0007 (4)
C50.0272 (6)0.0235 (6)0.0237 (6)0.0005 (5)0.0103 (5)0.0025 (5)
C60.0275 (6)0.0193 (6)0.0251 (6)0.0013 (5)0.0105 (5)0.0019 (4)
C70.0236 (6)0.0200 (6)0.0248 (6)0.0009 (4)0.0112 (5)0.0011 (4)
C80.0190 (5)0.0164 (5)0.0199 (5)0.0007 (4)0.0051 (4)0.0011 (4)
C90.0207 (5)0.0184 (5)0.0215 (5)0.0024 (4)0.0082 (4)0.0015 (4)
C100.0202 (5)0.0205 (5)0.0234 (5)0.0003 (4)0.0071 (4)0.0043 (4)
C110.0202 (5)0.0184 (5)0.0188 (5)0.0004 (4)0.0056 (4)0.0012 (4)
C120.0193 (5)0.0181 (5)0.0225 (5)0.0003 (4)0.0044 (4)0.0018 (4)
C130.0229 (6)0.0201 (5)0.0244 (6)0.0005 (4)0.0038 (4)0.0045 (4)
C140.0253 (6)0.0255 (6)0.0202 (5)0.0022 (5)0.0074 (4)0.0024 (4)
C150.0217 (5)0.0212 (6)0.0223 (5)0.0003 (4)0.0082 (4)0.0011 (4)
C160.0184 (5)0.0158 (5)0.0204 (5)0.0010 (4)0.0051 (4)0.0004 (4)
C170.0219 (6)0.0191 (5)0.0260 (6)0.0012 (4)0.0050 (5)0.0008 (4)
C180.0206 (5)0.0156 (5)0.0194 (5)0.0003 (4)0.0061 (4)0.0022 (4)
Geometric parameters (Å, º) top
O1—C181.2724 (14)C6—C71.3705 (17)
O2—C181.2439 (14)C6—H60.9500
O3—C171.3195 (15)C7—C81.4085 (16)
O3—H3A0.8400C7—H70.9500
O4—C171.2132 (15)C8—C91.4102 (16)
N1—C51.3337 (16)C9—C101.3637 (17)
N1—C11.3438 (16)C9—H90.9500
N2—C61.3445 (16)C10—H100.9500
N2—C101.3454 (16)C11—C161.3939 (15)
N2—H2A0.8800C11—C121.3945 (16)
N3—C81.3654 (15)C11—H110.9500
N3—C31.3970 (14)C12—C131.3931 (17)
N3—H3B0.8800C12—C171.4969 (16)
C1—C21.3785 (17)C13—C141.3861 (17)
C1—H10.9500C13—H130.9500
C2—C31.3992 (16)C14—C151.3905 (17)
C2—H2B0.9500C14—H140.9500
C3—C41.3966 (16)C15—C161.3990 (16)
C4—C51.3886 (17)C15—H150.9500
C4—H40.9500C16—C181.5153 (15)
C5—H50.9500
C17—O3—H3A109.5C7—C8—C9117.53 (10)
C5—N1—C1117.08 (10)C10—C9—C8120.09 (11)
C6—N2—C10120.50 (10)C10—C9—H9120.0
C6—N2—H2A119.7C8—C9—H9120.0
C10—N2—H2A119.7N2—C10—C9121.00 (11)
C8—N3—C3129.89 (10)N2—C10—H10119.5
C8—N3—H3B115.1C9—C10—H10119.5
C3—N3—H3B115.1C16—C11—C12120.54 (11)
N1—C1—C2123.29 (11)C16—C11—H11119.7
N1—C1—H1118.4C12—C11—H11119.7
C2—C1—H1118.4C13—C12—C11119.68 (11)
C1—C2—C3119.45 (11)C13—C12—C17118.47 (10)
C1—C2—H2B120.3C11—C12—C17121.84 (11)
C3—C2—H2B120.3C14—C13—C12120.20 (11)
C4—C3—N3125.00 (11)C14—C13—H13119.9
C4—C3—C2117.57 (11)C12—C13—H13119.9
N3—C3—C2117.35 (10)C13—C14—C15119.99 (11)
C5—C4—C3118.54 (11)C13—C14—H14120.0
C5—C4—H4120.7C15—C14—H14120.0
C3—C4—H4120.7C14—C15—C16120.47 (11)
N1—C5—C4124.07 (11)C14—C15—H15119.8
N1—C5—H5118.0C16—C15—H15119.8
C4—C5—H5118.0C11—C16—C15119.05 (10)
N2—C6—C7121.62 (11)C11—C16—C18121.14 (10)
N2—C6—H6119.2C15—C16—C18119.81 (10)
C7—C6—H6119.2O4—C17—O3123.57 (11)
C6—C7—C8119.23 (11)O4—C17—C12122.35 (11)
C6—C7—H7120.4O3—C17—C12114.07 (10)
C8—C7—H7120.4O2—C18—O1124.29 (11)
N3—C8—C7124.80 (10)O2—C18—C16118.37 (10)
N3—C8—C9117.60 (10)O1—C18—C16117.33 (10)
C7—C8—C3—C432.47 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.881.842.7134 (14)174
O3—H3A···N1ii0.841.832.6720 (14)178
N3—H3B···O1iii0.881.942.7987 (13)166
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x1/2, y+1/2, z+1/2.
 

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