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Acta Cryst. (2007). E63, o3303
https://doi.org/10.1107/S1600536807029856
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Bis(dicyclo­hexyl­ammonium 4-hydroxy­benzoate)

S. M. Zain and S. W. Ng
In the crystal structure of the title compound, 2C12H24N+·2C7H5O3-, the cation is linked to the single-bonded carboxylate O atom of an anion as well as to the double-bonded carbonyl O atom of another anion to form a centrosymmetric hydrogen-bonded ion pair. Adjacent ion pairs are linked through the hydr­oxy group of the anion to produce a honeycomb-like layer structure.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029856/tk2167sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029856/tk2167Isup2.hkl
Contains datablock I

CCDC reference: 655025

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.135
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.05 Ratio


Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.74
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H1<I>N<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H2<I>N<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H3<I>O<


Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         29


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   6 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

4-Hydroxybenzoic acid is an excellent counterion for the engineering of ammonium salts that exhibit second-harmonic generation, as noted from the SHG activity of (S)-ethylphenylammonium 4-hydroxybenzoate (Aakeröy et al., 1993). The anion is capable of mutiple hydrogen bonding interactions, this feature is crucial to chemical stability. We have previously used the sterically crowded dicyclohexylammonium cation in the synthesis of monocarboxylates (Ng, 1996; Ng, 1997; Ng, 1998; Ng & Hook, 1999; Ng et al., 1999, 2001; Subramanian et al., 2000) but these monocarboxylates do not have hydrogen-bond donor sites. Our studies are now extended to a study of dicyclohexylammonium 4-hydroxybenzoate, which exists as a hydrogen-bonded dimeric ion-pair that is linked across a center-of-inversion (Fig. 1). The ammonium hydrogen serves as as donor to a single-bond carboxyl oxygen atom of one anion as well as to the double-bond carbonyl oxygen atom of the symmetry-related anion. The carboxylate –CO2 unit has localized bonds: the hydrogen bond to the negatively-charged oxygen atom is significantly longer than that to the neutral oxygen atom. The hydroxy group engages in linking adjacent dimeric ion-pairs into a layer motif (Table 1, Fig. 2). The layer has a honeycomb-like topology (Fig. 3) but is buckled.

The crystal structures of polymethyleneiminium 4-hydroxybenzoates, [(CH2)nNH2] [C7H5O3] (n = 4, 5 and 6) have been reported; the hexamethyleneiminiums exists in two modifications (Moritani et al., 1987). The compounds, whose carboxylate groups are also localized, adopt chain motif instead, a motif that is also adopted by dicyclohexylammonium trifluoroacetate (Ng et al., 1999).

Related literature top

For crystal structures of dicyclohexylammonium salts of monocarboxylic acids, see Ng (1996, 1997, 1998), Ng et al. (1999, 2001), Ng & Hook (1999), Subramanian et al. (2000). For crystal structures of other ammonium salts of 4-hydroxybenzoic acid, see Moritani et al. (1987). For related literature, see: Aakeröy et al. (1993); Subramanian et al. (2000).

Experimental top

Dicyclohexylamine (0.17 g, 1 mmol) and 4-hydroxybenzoic acid (0.14 g, 1 mmol) were dissolved in ethanol (25 ml). The mixture was heated to dissolve the reactants. Colorless plates of the salt separated from the solution after several days.

Refinement top

All hydrogen atoms were located in difference Fourier maps, and were refined with distance restraints C–H = 0.95±0.01 Å and N–H = O–H = 0.85±0.01 Å. The temperature factors were refined freely.

Structure description top

4-Hydroxybenzoic acid is an excellent counterion for the engineering of ammonium salts that exhibit second-harmonic generation, as noted from the SHG activity of (S)-ethylphenylammonium 4-hydroxybenzoate (Aakeröy et al., 1993). The anion is capable of mutiple hydrogen bonding interactions, this feature is crucial to chemical stability. We have previously used the sterically crowded dicyclohexylammonium cation in the synthesis of monocarboxylates (Ng, 1996; Ng, 1997; Ng, 1998; Ng & Hook, 1999; Ng et al., 1999, 2001; Subramanian et al., 2000) but these monocarboxylates do not have hydrogen-bond donor sites. Our studies are now extended to a study of dicyclohexylammonium 4-hydroxybenzoate, which exists as a hydrogen-bonded dimeric ion-pair that is linked across a center-of-inversion (Fig. 1). The ammonium hydrogen serves as as donor to a single-bond carboxyl oxygen atom of one anion as well as to the double-bond carbonyl oxygen atom of the symmetry-related anion. The carboxylate –CO2 unit has localized bonds: the hydrogen bond to the negatively-charged oxygen atom is significantly longer than that to the neutral oxygen atom. The hydroxy group engages in linking adjacent dimeric ion-pairs into a layer motif (Table 1, Fig. 2). The layer has a honeycomb-like topology (Fig. 3) but is buckled.

The crystal structures of polymethyleneiminium 4-hydroxybenzoates, [(CH2)nNH2] [C7H5O3] (n = 4, 5 and 6) have been reported; the hexamethyleneiminiums exists in two modifications (Moritani et al., 1987). The compounds, whose carboxylate groups are also localized, adopt chain motif instead, a motif that is also adopted by dicyclohexylammonium trifluoroacetate (Ng et al., 1999).

For crystal structures of dicyclohexylammonium salts of monocarboxylic acids, see Ng (1996, 1997, 1998), Ng et al. (1999, 2001), Ng & Hook (1999), Subramanian et al. (2000). For crystal structures of other ammonium salts of 4-hydroxybenzoic acid, see Moritani et al. (1987). For related literature, see: Aakeröy et al. (1993); Subramanian et al. (2000).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the hydrogen-bonded dimer; displacement ellipsoids are drawn at the 70% probability level. The dashed lines denote hydrogen bonds. [Symmetry code i: 1 – x, 1 – y, 1 – z.]
[Figure 2] Fig. 2. Layer structure; displacement ellipsoids are drawn at the 70% probability level. The dashed lines denote hydrogen bonds, and the atoms constituting the 12-membered O–C=O···H–N–H···O–C=O···H–N–H··· ring are shown with their van der Waals surfaces.
[Figure 3] Fig. 3. OLEX depiction of the (6,3)-honeycomb topology, shown projected against the unit cell.
Bis(dicyclohexylammonium 4-hydroxybenzoate) top
Crystal data top
2C12H24N+·2C7H5O3−F(000) = 696
Mr = 638.86Dx = 1.156 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9647 reflections
a = 9.4779 (2) Åθ = 2.4–34.6°
b = 11.0650 (3) ŵ = 0.08 mm−1
c = 17.5816 (4) ÅT = 173 K
β = 95.431 (1)°Plate, colorless
V = 1835.56 (8) Å30.35 × 0.30 × 0.06 mm
Z = 2
Data collection top
Bruker APEX2 area-detector
diffractometer		4227 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 30.0°, θmin = 2.6°
φ and ω scansh = −13→13
32008 measured reflectionsk = −15→15
5346 independent reflectionsl = −24→24
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.5355P]
where P = (Fo2 + 2Fc2)/3
5346 reflections(Δ/σ)max = 0.001
324 parametersΔρmax = 0.52 e Å−3
29 restraintsΔρmin = −0.19 e Å−3
Crystal data top
2C12H24N+·2C7H5O3−V = 1835.56 (8) Å3
Mr = 638.86Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.4779 (2) ŵ = 0.08 mm−1
b = 11.0650 (3) ÅT = 173 K
c = 17.5816 (4) Å0.35 × 0.30 × 0.06 mm
β = 95.431 (1)°
Data collection top
Bruker APEX2 area-detector
diffractometer		4227 reflections with I > 2σ(I)
32008 measured reflectionsRint = 0.033
5346 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04529 restraints
wR(F2) = 0.135All H-atom parameters refined
S = 1.04Δρmax = 0.52 e Å−3
5346 reflectionsΔρmin = −0.19 e Å−3
324 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3950 (1)0.6161 (1)0.3722 (1)0.0201 (2)
O20.2552 (1)0.6278 (1)0.4673 (1)0.0238 (2)
O30.0294 (1)1.0816 (1)0.2716 (1)0.0224 (2)
N10.6664 (1)0.5639 (1)0.4429 (1)0.0159 (2)
C10.7400 (1)0.5365 (1)0.3728 (1)0.0193 (2)
C20.9009 (1)0.5378 (2)0.3891 (1)0.0312 (3)
C30.9688 (2)0.5083 (2)0.3159 (1)0.0472 (5)
C40.9177 (2)0.3876 (2)0.2818 (1)0.0439 (4)
C50.7560 (1)0.3837 (1)0.2691 (1)0.0305 (3)
C60.6884 (1)0.4135 (1)0.3423 (1)0.0224 (2)
C70.7084 (1)0.6764 (1)0.4870 (1)0.0163 (2)
C80.6200 (1)0.6816 (1)0.5551 (1)0.0185 (2)
C90.6546 (1)0.7949 (1)0.6030 (1)0.0210 (2)
C100.6305 (1)0.9076 (1)0.5536 (1)0.0222 (2)
C110.7201 (1)0.9028 (1)0.4858 (1)0.0227 (2)
C120.6889 (1)0.7891 (1)0.4374 (1)0.0201 (2)
C130.2947 (1)0.6642 (1)0.4052 (1)0.0165 (2)
C140.2207 (1)0.7721 (1)0.3683 (1)0.0152 (2)
C150.2559 (1)0.8142 (1)0.2979 (1)0.0182 (2)
C160.1924 (1)0.9166 (1)0.2646 (1)0.0194 (2)
C170.0917 (1)0.9792 (1)0.3017 (1)0.0178 (2)
C180.0528 (1)0.9369 (1)0.3717 (1)0.0190 (2)
C190.1173 (1)0.8343 (1)0.4046 (1)0.0176 (2)
H3o0.063 (2)1.096 (2)0.228 (1)0.052 (6)*
H1n0.577 (1)0.571 (1)0.428 (1)0.019 (3)*
H2n0.680 (2)0.503 (1)0.473 (1)0.036 (4)*
H10.709 (2)0.597 (1)0.337 (1)0.022 (4)*
H210.929 (2)0.481 (1)0.429 (1)0.036 (4)*
H220.933 (2)0.615 (1)0.409 (1)0.038 (5)*
H311.069 (1)0.507 (2)0.327 (1)0.061 (6)*
H320.949 (3)0.570 (2)0.278 (1)0.077 (8)*
H410.946 (2)0.323 (1)0.318 (1)0.049 (6)*
H420.959 (2)0.372 (2)0.235 (1)0.054 (6)*
H510.727 (2)0.304 (1)0.253 (1)0.044 (5)*
H520.728 (2)0.445 (1)0.232 (1)0.029 (4)*
H610.587 (1)0.414 (1)0.334 (1)0.024 (4)*
H620.713 (2)0.355 (1)0.381 (1)0.034 (4)*
H70.807 (1)0.667 (1)0.505 (1)0.020 (3)*
H810.635 (2)0.610 (1)0.585 (1)0.023 (4)*
H820.522 (1)0.685 (2)0.536 (1)0.030 (4)*
H910.753 (1)0.795 (1)0.625 (1)0.026 (4)*
H920.595 (1)0.796 (1)0.645 (1)0.024 (4)*
H1010.651 (2)0.979 (1)0.583 (1)0.028 (4)*
H1020.532 (1)0.911 (1)0.533 (1)0.022 (4)*
H1110.818 (1)0.906 (1)0.506 (1)0.026 (4)*
H1120.706 (2)0.975 (1)0.455 (1)0.028 (4)*
H1210.594 (1)0.790 (1)0.413 (1)0.024 (4)*
H1220.751 (1)0.787 (2)0.398 (1)0.028 (4)*
H150.324 (1)0.769 (1)0.272 (1)0.026 (4)*
H160.218 (2)0.947 (2)0.217 (1)0.028 (4)*
H18−0.017 (1)0.981 (1)0.395 (1)0.029 (4)*
H190.096 (2)0.807 (1)0.453 (1)0.026 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0204 (4)0.0178 (4)0.0214 (4)0.0044 (3)−0.0021 (3)−0.0041 (3)
O20.0307 (4)0.0195 (4)0.0211 (4)0.0056 (3)0.0024 (3)0.0052 (3)
O30.0265 (4)0.0160 (4)0.0247 (4)0.0036 (3)0.0019 (3)0.0053 (3)
N10.0173 (4)0.0147 (4)0.0156 (4)0.0007 (3)0.0007 (3)−0.0009 (3)
C10.0183 (5)0.0226 (5)0.0172 (5)0.0011 (4)0.0027 (4)−0.0052 (4)
C20.0187 (5)0.0415 (8)0.0334 (7)−0.0008 (5)0.0019 (5)−0.0174 (6)
C30.0210 (6)0.0725 (13)0.0499 (9)−0.0063 (7)0.0127 (6)−0.0310 (9)
C40.0272 (7)0.0609 (11)0.0439 (9)0.0101 (7)0.0050 (6)−0.0269 (8)
C50.0275 (6)0.0362 (7)0.0280 (6)0.0029 (5)0.0029 (5)−0.0136 (6)
C60.0225 (5)0.0226 (6)0.0216 (5)0.0022 (4)0.0001 (4)−0.0066 (4)
C70.0191 (5)0.0139 (5)0.0157 (5)−0.0006 (4)−0.0001 (4)−0.0019 (4)
C80.0255 (5)0.0151 (5)0.0148 (5)0.0004 (4)0.0020 (4)0.0001 (4)
C90.0287 (6)0.0180 (5)0.0163 (5)0.0008 (4)0.0014 (4)−0.0020 (4)
C100.0284 (6)0.0148 (5)0.0234 (5)0.0006 (4)0.0037 (4)−0.0017 (4)
C110.0290 (6)0.0153 (5)0.0242 (6)−0.0032 (4)0.0049 (4)0.0005 (4)
C120.0262 (5)0.0171 (5)0.0170 (5)−0.0025 (4)0.0028 (4)0.0017 (4)
C130.0177 (5)0.0127 (5)0.0182 (5)−0.0005 (4)−0.0030 (4)−0.0019 (4)
C140.0154 (4)0.0128 (5)0.0169 (5)−0.0005 (4)−0.0005 (3)−0.0002 (4)
C150.0182 (5)0.0187 (5)0.0177 (5)0.0004 (4)0.0025 (4)−0.0010 (4)
C160.0216 (5)0.0201 (5)0.0166 (5)−0.0007 (4)0.0017 (4)0.0027 (4)
C170.0187 (5)0.0136 (5)0.0204 (5)−0.0015 (4)−0.0019 (4)0.0013 (4)
C180.0188 (5)0.0160 (5)0.0227 (5)0.0018 (4)0.0045 (4)−0.0005 (4)
C190.0190 (5)0.0161 (5)0.0179 (5)−0.0007 (4)0.0035 (4)0.0013 (4)
Geometric parameters (Å, º) top
O1—C131.276 (1)C1—H10.95 (1)
O2—C131.254 (1)C2—H210.96 (1)
O3—C171.362 (1)C2—H220.96 (1)
N1—C11.503 (1)C3—H310.95 (1)
N1—C71.501 (1)C3—H320.96 (1)
C1—C21.525 (2)C4—H410.97 (1)
C1—C61.526 (2)C4—H420.96 (1)
C2—C31.528 (2)C5—H510.96 (1)
C3—C41.524 (2)C5—H520.96 (1)
C4—C51.529 (2)C6—H610.96 (1)
C5—C61.528 (2)C6—H620.95 (1)
C7—C121.523 (2)C7—H70.96 (1)
C7—C81.526 (2)C9—H910.97 (1)
C9—C101.525 (2)C9—H920.97 (1)
C9—C81.528 (2)C10—H1010.96 (1)
C10—C111.528 (2)C10—H1020.97 (1)
C11—C121.532 (2)C11—H1110.96 (1)
C13—C141.500 (2)C11—H1120.97 (1)
C14—C151.393 (2)C8—H810.95 (1)
C14—C191.399 (2)C8—H820.96 (1)
C15—C161.386 (2)C12—H1210.96 (1)
C16—C171.390 (2)C12—H1220.96 (1)
C17—C181.399 (2)C15—H150.97 (1)
C18—C191.390 (2)C16—H160.96 (1)
O3—H3o0.87 (1)C18—H180.95 (1)
N1—H1n0.87 (1)C19—H190.95 (1)
N1—H2n0.86 (1)
C1—N1—C7118.0 (1)C5—C4—H41107 (1)
N1—C1—C2112.2 (1)C3—C4—H42111 (1)
N1—C1—C6108.0 (1)C5—C4—H42111 (1)
C2—C1—C6110.9 (1)H41—C4—H42108 (2)
C1—C2—C3109.5 (1)C6—C5—H51108 (1)
C4—C3—C2112.0 (2)C4—C5—H51109 (1)
C3—C4—C5111.1 (1)C6—C5—H52108 (1)
C6—C5—C4111.4 (1)C4—C5—H52107 (1)
C1—C6—C5110.1 (1)H51—C5—H52114 (2)
N1—C7—C12111.8 (1)C1—C6—H61110 (1)
N1—C7—C8107.4 (1)C5—C6—H61111 (1)
C12—C7—C8111.9 (1)C1—C6—H62108 (1)
C10—C9—C8110.2 (1)C5—C6—H62111 (1)
C9—C10—C11110.6 (1)H61—C6—H62107 (1)
C10—C11—C12111.6 (1)N1—C7—H7106 (1)
C7—C8—C9111.0 (1)C12—C7—H7110 (1)
C7—C12—C11110.4 (1)C8—C7—H7110 (1)
O1—C13—O2124.0 (1)C10—C9—H91108 (1)
O2—C13—C14117.7 (1)C8—C9—H91111 (1)
O1—C13—C14118.3 (1)C10—C9—H92111 (1)
C15—C14—C19118.5 (1)C8—C9—H92109 (1)
C15—C14—C13120.6 (1)H91—C9—H92108 (1)
C19—C14—C13120.9 (1)C9—C10—H101111 (1)
C16—C15—C14121.2 (1)C11—C10—H101111 (1)
C15—C16—C17119.9 (1)C9—C10—H102109 (1)
O3—C17—C16121.6 (1)C11—C10—H102107 (1)
O3—C17—C18118.6 (1)H101—C10—H102108 (1)
C16—C17—C18119.7 (1)C10—C11—H111108 (1)
C19—C18—C17119.9 (1)C12—C11—H111111 (1)
C18—C19—C14120.8 (1)C10—C11—H112110 (1)
C17—O3—H3o108 (1)C12—C11—H112111 (1)
C7—N1—H1n107 (1)H111—C11—H112105 (1)
C1—N1—H1n106 (1)C7—C8—H81109 (1)
C7—N1—H2n108 (1)C9—C8—H81112 (1)
C1—N1—H2n107 (1)C7—C8—H82109 (1)
H1n—N1—H2n110 (2)C9—C8—H82108 (1)
N1—C1—H1106 (1)H81—C8—H82108 (1)
C2—C1—H1111 (1)C7—C12—H121109 (1)
C6—C1—H1109 (1)C11—C12—H121111 (1)
C1—C2—H21110 (1)C7—C12—H122111 (1)
C3—C2—H21111 (1)C11—C12—H122109 (1)
C1—C2—H22110 (1)H121—C12—H122107 (1)
C3—C2—H22110 (1)C16—C15—H15120 (1)
H21—C2—H22106 (2)C14—C15—H15119 (1)
C4—C3—H31110 (1)C15—C16—H16121 (1)
C2—C3—H31109 (1)C17—C16—H16119 (1)
C4—C3—H32108 (2)C19—C18—H18122 (1)
C2—C3—H32112 (2)C17—C18—H18118 (1)
H31—C3—H32106 (2)C18—C19—H19121 (1)
C3—C4—H41109 (1)C14—C19—H19119 (1)
C7—N1—C1—C252.8 (1)N1—C7—C12—C11175.0 (1)
C7—N1—C1—C6175.3 (1)C8—C7—C12—C1154.5 (1)
N1—C1—C2—C3179.5 (1)C10—C11—C12—C7−55.0 (1)
C6—C1—C2—C358.7 (2)O2—C13—C14—C15−177.6 (1)
C1—C2—C3—C4−56.6 (2)O1—C13—C14—C153.4 (2)
C2—C3—C4—C554.6 (2)O2—C13—C14—C193.9 (2)
C3—C4—C5—C6−54.1 (2)O1—C13—C14—C19−175.1 (1)
N1—C1—C6—C5177.8 (1)C19—C14—C15—C161.1 (2)
C2—C1—C6—C5−58.9 (1)C13—C14—C15—C16−177.4 (1)
C4—C5—C6—C156.3 (2)C14—C15—C16—C170.0 (2)
C1—N1—C7—C1257.7 (1)C15—C16—C17—O3178.5 (1)
C1—N1—C7—C8−179.2 (1)C15—C16—C17—C18−1.3 (2)
C8—C9—C10—C11−57.5 (1)O3—C17—C18—C19−178.4 (1)
C9—C10—C11—C1257.0 (1)C16—C17—C18—C191.5 (2)
N1—C7—C8—C9−179.3 (1)C17—C18—C19—C14−0.4 (2)
C12—C7—C8—C9−56.2 (1)C15—C14—C19—C18−1.0 (2)
C10—C9—C8—C757.1 (1)C13—C14—C19—C18177.6 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.87 (1)1.96 (1)2.808 (1)164 (1)
N1—H2n···O2i0.86 (1)1.85 (1)2.706 (1)169 (2)
O3—H3o···O1ii0.87 (1)1.86 (1)2.719 (1)170 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula2C12H24N+·2C7H5O3−
Mr638.86
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.4779 (2), 11.0650 (3), 17.5816 (4)
β (°) 95.431 (1)
V (Å3)1835.56 (8)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.30 × 0.06
Data collection
DiffractometerBruker APEX2 area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		32008, 5346, 4227
Rint0.033
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.135, 1.04
No. of reflections5346
No. of parameters324
No. of restraints29
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.52, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.87 (1)1.96 (1)2.808 (1)164 (1)
N1—H2n···O2i0.86 (1)1.85 (1)2.706 (1)169 (2)
O3—H3o···O1ii0.87 (1)1.86 (1)2.719 (1)170 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2.
 

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