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The title compound, C6H10N22+·2C8H5O4, is a proton-transfer compound obtained from 1,4-phenyl­enediamine and phthalic acid. The asymmetric unit contains half of a centrosymmetric cation and an anion. A strong intra­molecular O—H...O hydrogen bond is found in the anion. The cations and anions are linked through a number of inter­molecular N—H...O hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051245/tk2101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051245/tk2101Isup2.hkl
Contains datablock I

CCDC reference: 634062

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.096
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT772_ALERT_2_A Suspect O-H Bond in CIF: O3 -H2O .. 1.34 Ang.
Author Response: This is because of intramolecular hydrogen bond. Such mode is common in hydrogen phthalate.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety N PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sieens, 1994); software used to prepare material for publication: SHELXTL.

1,4-Phenylenediammonium bis(hydrogen phthalate) top
Crystal data top
C6H10N22+·2C8H5O4Z = 1
Mr = 440.40F(000) = 230
Triclinic, P1Dx = 1.481 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0828 (6) ÅCell parameters from 4586 reflections
b = 8.2286 (7) Åθ = 3.1–27.6°
c = 9.4515 (8) ŵ = 0.11 mm1
α = 92.442 (3)°T = 153 K
β = 114.897 (2)°Prism, red
γ = 115.694 (2)°0.51 × 0.37 × 0.30 mm
V = 493.95 (7) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2078 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.013
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1010
4890 measured reflectionsk = 1010
2248 independent reflectionsl = 1012
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.061P)2 + 0.1408P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2248 reflectionsΔρmax = 0.39 e Å3
151 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (8)
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
O10.16640 (11)0.54970 (11)0.19791 (9)0.02330 (19)
O20.11306 (12)0.61895 (12)0.39501 (9)0.0268 (2)
O30.31560 (12)0.81017 (12)0.67151 (9)0.0250 (2)
O40.64278 (13)1.03252 (11)0.83848 (10)0.0285 (2)
N0.26136 (13)0.68470 (11)0.92814 (10)0.01613 (19)
H0A0.12470.60020.89550.019*
H0B0.26940.73880.84750.019*
H0C0.31370.77471.01860.019*
C10.23820 (15)0.62444 (14)0.34154 (12)0.0174 (2)
C20.47294 (14)0.71748 (13)0.45562 (11)0.0154 (2)
C30.57898 (16)0.67266 (15)0.38994 (12)0.0197 (2)
H30.50050.59100.28340.024*
C40.79407 (17)0.74292 (16)0.47457 (13)0.0235 (2)
H40.86130.70920.42690.028*
C50.91014 (16)0.86282 (16)0.62943 (14)0.0254 (2)
H51.05810.91310.68870.031*
C60.80899 (16)0.90891 (15)0.69718 (13)0.0222 (2)
H60.89010.99130.80360.027*
C70.59121 (15)0.83860 (13)0.61464 (12)0.0162 (2)
C80.51163 (16)0.90076 (14)0.71386 (12)0.0190 (2)
C90.38396 (15)0.58895 (13)0.96473 (11)0.0152 (2)
C100.59760 (15)0.69210 (13)1.01699 (12)0.0179 (2)
H100.66290.82321.02810.022*
C110.71550 (15)0.60195 (14)1.05294 (12)0.0178 (2)
H110.86210.67051.08910.021*
H2O0.201 (3)0.697 (3)0.521 (3)0.072 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0183 (4)0.0300 (4)0.0158 (4)0.0092 (3)0.0069 (3)0.0012 (3)
O20.0172 (4)0.0418 (5)0.0209 (4)0.0141 (3)0.0100 (3)0.0030 (3)
O30.0247 (4)0.0370 (4)0.0210 (4)0.0178 (3)0.0149 (3)0.0070 (3)
O40.0355 (4)0.0252 (4)0.0236 (4)0.0162 (4)0.0131 (4)0.0013 (3)
N0.0170 (4)0.0179 (4)0.0149 (4)0.0098 (3)0.0079 (3)0.0026 (3)
C10.0172 (4)0.0192 (5)0.0179 (5)0.0096 (4)0.0096 (4)0.0063 (4)
C20.0159 (4)0.0170 (4)0.0160 (5)0.0086 (4)0.0093 (4)0.0065 (4)
C30.0210 (5)0.0250 (5)0.0167 (4)0.0129 (4)0.0107 (4)0.0054 (4)
C40.0220 (5)0.0320 (6)0.0253 (5)0.0165 (4)0.0155 (4)0.0088 (4)
C50.0157 (4)0.0309 (6)0.0268 (5)0.0107 (4)0.0091 (4)0.0061 (4)
C60.0189 (5)0.0216 (5)0.0197 (5)0.0075 (4)0.0073 (4)0.0015 (4)
C70.0184 (5)0.0156 (4)0.0178 (5)0.0092 (4)0.0107 (4)0.0056 (4)
C80.0263 (5)0.0204 (5)0.0173 (5)0.0153 (4)0.0124 (4)0.0072 (4)
C90.0176 (4)0.0186 (5)0.0112 (4)0.0106 (4)0.0072 (4)0.0026 (3)
C100.0184 (5)0.0150 (4)0.0184 (5)0.0072 (4)0.0086 (4)0.0033 (4)
C110.0148 (4)0.0186 (5)0.0176 (5)0.0069 (4)0.0077 (4)0.0031 (4)
Geometric parameters (Å, º) top
O1—C11.2304 (12)C3—H30.9500
O2—C11.2935 (12)C4—C51.3834 (16)
O2—H2O1.07 (2)C4—H40.9500
O3—C81.2817 (13)C5—C61.3825 (15)
O3—H2O1.34 (2)C5—H50.9500
O4—C81.2369 (13)C6—C71.4015 (14)
N—C91.4608 (11)C6—H60.9500
N—H0A0.9100C7—C81.5189 (13)
N—H0B0.9100C9—C11i1.3825 (14)
N—H0C0.9100C9—C101.3862 (13)
C1—C21.5153 (13)C10—C111.3913 (13)
C2—C31.3995 (13)C10—H100.9500
C2—C71.4151 (13)C11—C9i1.3825 (14)
C3—C41.3837 (14)C11—H110.9500
C1—O2—H2O110.5 (12)C6—C5—H5120.3
C8—O3—H2O111.3 (9)C4—C5—H5120.3
C9—N—H0A109.5C5—C6—C7122.43 (10)
C9—N—H0B109.5C5—C6—H6118.8
H0A—N—H0B109.5C7—C6—H6118.8
C9—N—H0C109.5C6—C7—C2118.08 (9)
H0A—N—H0C109.5C6—C7—C8113.76 (9)
H0B—N—H0C109.5C2—C7—C8128.14 (9)
O1—C1—O2120.02 (9)O4—C8—O3122.49 (9)
O1—C1—C2119.45 (9)O4—C8—C7117.79 (9)
O2—C1—C2120.50 (9)O3—C8—C7119.60 (9)
C3—C2—C7118.38 (9)C11i—C9—C10121.61 (9)
C3—C2—C1113.26 (8)C11i—C9—N119.28 (8)
C7—C2—C1128.36 (8)C10—C9—N119.11 (8)
C4—C3—C2122.38 (9)C9—C10—C11119.40 (9)
C4—C3—H3118.8C9—C10—H10120.3
C2—C3—H3118.8C11—C10—H10120.3
C5—C4—C3119.29 (9)C9i—C11—C10118.99 (9)
C5—C4—H4120.4C9i—C11—H11120.5
C3—C4—H4120.4C10—C11—H11120.5
C6—C5—C4119.44 (9)
O1—C1—C2—C312.91 (13)C3—C2—C7—C60.71 (14)
O2—C1—C2—C3165.29 (9)C1—C2—C7—C6179.67 (9)
O1—C1—C2—C7167.46 (9)C3—C2—C7—C8177.23 (9)
O2—C1—C2—C714.34 (15)C1—C2—C7—C82.38 (16)
C7—C2—C3—C40.24 (15)C6—C7—C8—O414.58 (13)
C1—C2—C3—C4179.91 (9)C2—C7—C8—O4167.40 (9)
C2—C3—C4—C50.40 (16)C6—C7—C8—O3161.70 (9)
C3—C4—C5—C60.54 (17)C2—C7—C8—O316.32 (15)
C4—C5—C6—C70.05 (17)C11i—C9—C10—C110.12 (16)
C5—C6—C7—C20.59 (16)N—C9—C10—C11179.63 (8)
C5—C6—C7—C8177.65 (10)C9—C10—C11—C9i0.12 (15)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O31.07 (2)1.34 (2)2.4081 (11)174 (2)
N—H0A···O1ii0.911.862.7654 (11)170
N—H0B···O30.911.922.8032 (11)165
N—H0C···O4iii0.911.842.7278 (11)163
Symmetry codes: (ii) x, y+1, z+1; (iii) x+1, y+2, z+2.
 

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