Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The structures of the proton-transfer compounds of 4,5-di­chloro­phthalic acid (DCPA) with the aliphatic Lewis bases triethyl­amine, diethyl­amine, n-butyl­amine and piperidine, namely triethyl­aminium 2-carb­oxy-4,5-dichloro­benzoate, C6H16N+·C8H3Cl2O4, (I), diethyl­aminium 2-carb­oxy-4,5-dichloro­benzoate, C4H12N+·C8H3Cl2O4, (II), bis­(butan­aminium) 4,5-dichloro­benzene-1,2-dicarboxylate monohydrate, 2C4H12N+·C8H2Cl2O42−·H2O, (III), and bis(piperidinium) 4,5-dichloro­benzene-1,2-dicarboxylate monohydrate, 2C5H12N+·C8H2Cl2O42−·H2O, (IV), have been determined at 200 K. All compounds have hydrogen-bonding associations, giving discrete cation–anion units in (I) and linear chains in (II), while (III) and (IV) both have two-dimensional structures. In (I), a discrete cation–anion unit is formed through an asymmetric R12(4) N+—H...O2 hydrogen-bonding association, whereas in (II), chains are formed through linear N—H...O associations involving both aminium H-atom donors. In compounds (III) and (IV), the primary N—H...O-linked cation–anion units are extended into a two-dimensional sheet structure via amide–carboxyl N—H...O and amide–carbonyl N—H...O inter­actions. In the 1:1 salts (I) and (II), the hydrogen 4,5-dichloro­phthalate anions are essentially planar with short intra­molecular carbox­yl–carboxyl O—H...O hydrogen bonds [O...O = 2.4223 (14) and 2.388 (2) Å, respectively]. This work provides a further example of the uncommon zero-dimensional hydrogen-bonded DCPA–Lewis base salt and the one-dimensional chain structure type, while even with the hydrate structures of the 1:2 salts with the primary and secondary amines, the low dimensionality generally associated with 1:1 DCPA salts is also found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110022328/gd3347sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022328/gd3347IVsup5.hkl
Contains datablock IV

CCDC references: 786826; 786827; 786828; 786829

Computing details top

For all compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (II), (IV); SIR92 (Altomare et al., 1994) for (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

(I) triethylaminium 2-carboxy-4,5-dichlorobenzoate top
Crystal data top
C6H16N+·C8H3Cl2O4F(000) = 704
Mr = 336.20Dx = 1.411 Mg m3
Monoclinic, P21/cMelting point: 353 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.3206 (7) ÅCell parameters from 5117 reflections
b = 11.2201 (7) Åθ = 3.2–28.8°
c = 19.4813 (12) ŵ = 0.42 mm1
β = 98.576 (7)°T = 200 K
V = 1582.3 (2) Å3Block, colourless
Z = 40.40 × 0.40 × 0.30 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
3098 independent reflections
Radiation source: Enhance (Mo) X-ray source2638 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.3°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.96, Tmax = 0.98l = 2024
10740 measured reflections
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.1656P]
where P = (Fo2 + 2Fc2)/3
3098 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1A0.05058 (17)0.95062 (10)0.36011 (6)0.0229 (3)
C1A0.2461 (2)0.91354 (14)0.36217 (7)0.0304 (4)
C1B0.0117 (2)1.07979 (12)0.37870 (7)0.0258 (4)
C1C0.0049 (2)0.91522 (13)0.29175 (7)0.0298 (4)
C2A0.3021 (2)0.92226 (15)0.43354 (8)0.0374 (5)
C2B0.1025 (2)1.16623 (13)0.32431 (8)0.0380 (5)
C2C0.2047 (3)0.94008 (18)0.28776 (10)0.0481 (6)
Cl40.57140 (5)0.69357 (4)0.68165 (2)0.0346 (1)
Cl50.53419 (6)0.40824 (4)0.68041 (2)0.0382 (1)
O110.15312 (15)0.31238 (9)0.44967 (5)0.0364 (4)
O120.05781 (15)0.46504 (9)0.38294 (5)0.0328 (3)
O210.05047 (15)0.68027 (9)0.39185 (5)0.0349 (3)
O220.18100 (15)0.82561 (9)0.45818 (5)0.0353 (3)
C10.24055 (17)0.50253 (13)0.49736 (6)0.0205 (4)
C20.25130 (17)0.62848 (12)0.49892 (6)0.0209 (4)
C30.35682 (17)0.68325 (13)0.55642 (6)0.0231 (4)
C40.44516 (18)0.61823 (13)0.61229 (7)0.0238 (4)
C50.42972 (18)0.49501 (13)0.61168 (7)0.0242 (4)
C60.33008 (18)0.43895 (12)0.55450 (7)0.0235 (4)
C110.14444 (19)0.41945 (13)0.44043 (7)0.0252 (4)
C210.15512 (18)0.71762 (13)0.44567 (7)0.0248 (4)
H1A0.019 (2)0.9082 (14)0.3943 (8)0.0300*
H120.057 (3)0.553 (2)0.3840 (11)0.0590*
H11A0.262400.830200.345700.0370*
H11B0.123501.092900.385400.0310*
H11C0.072800.959000.254000.0360*
H12A0.329400.964400.329800.0370*
H12B0.055701.097000.423300.0310*
H12C0.019000.829000.284200.0360*
H21A0.428600.892500.431900.0450*
H21B0.074301.248100.339900.0460*
H21C0.236900.906500.244700.0580*
H22A0.296301.005600.448700.0450*
H22B0.236601.154100.317400.0460*
H22C0.282000.903600.327600.0580*
H23A0.217900.874300.466300.0450*
H23B0.055401.152400.280500.0460*
H23C0.225401.026400.288400.0580*
H30.368100.767600.557100.0280*
H60.322400.354400.554100.0280*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0293 (6)0.0191 (6)0.0185 (6)0.0008 (5)0.0022 (5)0.0005 (4)
C1A0.0313 (8)0.0307 (8)0.0272 (7)0.0049 (7)0.0021 (6)0.0022 (6)
C1B0.0321 (8)0.0196 (7)0.0238 (7)0.0011 (6)0.0019 (6)0.0029 (5)
C1C0.0405 (8)0.0257 (8)0.0226 (7)0.0003 (7)0.0025 (6)0.0042 (6)
C2A0.0417 (9)0.0357 (9)0.0359 (9)0.0040 (7)0.0094 (7)0.0008 (7)
C2B0.0562 (11)0.0200 (8)0.0330 (8)0.0028 (7)0.0090 (7)0.0008 (6)
C2C0.0459 (10)0.0582 (12)0.0430 (10)0.0003 (9)0.0157 (8)0.0085 (8)
Cl40.0363 (2)0.0381 (2)0.0258 (2)0.0023 (2)0.0076 (2)0.0071 (2)
Cl50.0447 (2)0.0362 (2)0.0302 (2)0.0083 (2)0.0055 (2)0.0104 (2)
O110.0458 (7)0.0219 (6)0.0389 (6)0.0040 (5)0.0018 (5)0.0034 (4)
O120.0449 (6)0.0271 (6)0.0237 (5)0.0006 (5)0.0036 (5)0.0044 (4)
O210.0455 (6)0.0284 (6)0.0260 (5)0.0022 (5)0.0105 (5)0.0009 (4)
O220.0458 (6)0.0211 (6)0.0344 (6)0.0010 (5)0.0091 (5)0.0030 (4)
C10.0183 (6)0.0232 (7)0.0208 (7)0.0015 (6)0.0052 (5)0.0005 (5)
C20.0209 (7)0.0222 (7)0.0197 (7)0.0015 (5)0.0037 (5)0.0002 (5)
C30.0253 (7)0.0204 (7)0.0233 (7)0.0015 (6)0.0026 (5)0.0013 (5)
C40.0212 (7)0.0286 (8)0.0208 (7)0.0026 (6)0.0009 (5)0.0040 (6)
C50.0229 (7)0.0283 (8)0.0211 (7)0.0050 (6)0.0020 (5)0.0044 (6)
C60.0245 (7)0.0203 (7)0.0265 (7)0.0019 (6)0.0061 (6)0.0017 (5)
C110.0245 (7)0.0259 (8)0.0257 (7)0.0014 (6)0.0057 (6)0.0022 (6)
C210.0266 (7)0.0239 (8)0.0234 (7)0.0034 (6)0.0026 (6)0.0018 (6)
Geometric parameters (Å, º) top
Cl4—C41.7383 (14)C2A—H21A0.9800
Cl5—C51.7378 (14)C2A—H22A0.9800
O11—C111.2150 (18)C2A—H23A0.9800
O12—C111.3063 (17)C2B—H21B0.9800
O21—C211.2737 (17)C2B—H22B0.9800
O22—C211.2448 (18)C2B—H23B0.9800
O12—H120.99 (2)C2C—H21C0.9800
N1A—C1A1.4968 (19)C2C—H22C0.9800
N1A—C1B1.5106 (18)C2C—H23C0.9800
N1A—C1C1.5025 (18)C1—C21.415 (2)
N1A—H1A0.910 (15)C1—C111.5366 (19)
C1A—C2A1.510 (2)C1—C61.4000 (18)
C1B—C2B1.515 (2)C2—C31.4040 (17)
C1C—C2C1.502 (3)C2—C211.5344 (19)
C1A—H12A0.9900C3—C41.3875 (19)
C1A—H11A0.9900C4—C51.387 (2)
C1B—H11B0.9900C5—C61.3879 (19)
C1B—H12B0.9900C3—H30.9500
C1C—H12C0.9900C6—H60.9500
C1C—H11C0.9900
C11—O12—H12112.2 (12)H21B—C2B—H23B109.00
C1A—N1A—C1C109.65 (11)H22B—C2B—H23B110.00
C1B—N1A—C1C113.58 (11)C1B—C2B—H22B109.00
C1A—N1A—C1B114.02 (11)C1C—C2C—H21C109.00
C1B—N1A—H1A105.2 (10)C1C—C2C—H23C109.00
C1C—N1A—H1A108.3 (10)H21C—C2C—H22C109.00
C1A—N1A—H1A105.6 (9)C1C—C2C—H22C109.00
N1A—C1A—C2A113.49 (12)H22C—C2C—H23C109.00
N1A—C1B—C2B113.53 (11)H21C—C2C—H23C110.00
N1A—C1C—C2C113.00 (13)C2—C1—C6118.28 (11)
N1A—C1A—H12A109.00C2—C1—C11129.73 (11)
C2A—C1A—H11A109.00C6—C1—C11111.99 (12)
C2A—C1A—H12A109.00C1—C2—C3118.45 (11)
H11A—C1A—H12A108.00C1—C2—C21128.16 (11)
N1A—C1A—H11A109.00C3—C2—C21113.36 (12)
N1A—C1B—H11B109.00C2—C3—C4122.17 (13)
N1A—C1B—H12B109.00Cl4—C4—C5121.64 (11)
C2B—C1B—H12B109.00C3—C4—C5119.31 (13)
H11B—C1B—H12B108.00Cl4—C4—C3119.05 (11)
C2B—C1B—H11B109.00Cl5—C5—C6118.86 (11)
N1A—C1C—H11C109.00C4—C5—C6119.41 (13)
N1A—C1C—H12C109.00Cl5—C5—C4121.73 (11)
C2C—C1C—H12C109.00C1—C6—C5122.34 (13)
H11C—C1C—H12C108.00O11—C11—C1118.99 (12)
C2C—C1C—H11C109.00O12—C11—C1119.52 (12)
C1A—C2A—H22A110.00O11—C11—O12121.48 (13)
C1A—C2A—H23A109.00O21—C21—C2120.07 (12)
H21A—C2A—H22A109.00O22—C21—C2117.45 (12)
H21A—C2A—H23A109.00O21—C21—O22122.46 (13)
H22A—C2A—H23A109.00C2—C3—H3119.00
C1A—C2A—H21A109.00C4—C3—H3119.00
C1B—C2B—H21B109.00C1—C6—H6119.00
C1B—C2B—H23B109.00C5—C6—H6119.00
H21B—C2B—H22B109.00
C1B—N1A—C1A—C2A63.19 (16)C6—C1—C11—O12178.56 (12)
C1C—N1A—C1A—C2A168.20 (12)C1—C2—C3—C42.12 (19)
C1A—N1A—C1B—C2B69.93 (15)C21—C2—C3—C4175.95 (12)
C1C—N1A—C1B—C2B56.65 (16)C1—C2—C21—O210.1 (2)
C1A—N1A—C1C—C2C175.17 (13)C1—C2—C21—O22178.46 (13)
C1B—N1A—C1C—C2C55.98 (16)C3—C2—C21—O21177.98 (12)
C6—C1—C2—C32.37 (18)C3—C2—C21—O220.62 (17)
C6—C1—C2—C21175.38 (12)C2—C3—C4—Cl4179.47 (10)
C11—C1—C2—C3176.80 (12)C2—C3—C4—C50.12 (19)
C11—C1—C2—C215.5 (2)Cl4—C4—C5—Cl50.45 (17)
C2—C1—C6—C50.73 (19)Cl4—C4—C5—C6178.84 (10)
C11—C1—C6—C5178.57 (12)C3—C4—C5—Cl5179.14 (10)
C2—C1—C11—O11179.64 (13)C3—C4—C5—C61.6 (2)
C2—C1—C11—O120.7 (2)Cl5—C5—C6—C1179.42 (10)
C6—C1—C11—O110.44 (18)C4—C5—C6—C11.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O210.910 (15)2.569 (16)3.1614 (15)123.3 (12)
N1A—H1A···O220.910 (15)1.837 (15)2.7433 (16)173.7 (14)
O12—H12···O210.99 (2)1.44 (2)2.4223 (14)175 (2)
C3—H3···O220.952.292.6714 (16)103
C6—H6···O110.952.272.6602 (17)104
(II) diethylaminium 2-carboxy-4,5-dichlorobenzoate top
Crystal data top
C4H12N+·C8H3Cl2O4F(000) = 640
Mr = 308.14Dx = 1.392 Mg m3
Monoclinic, P21/cMelting point: 443 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.9588 (13) ÅCell parameters from 2315 reflections
b = 9.9042 (11) Åθ = 2.9–32.4°
c = 17.062 (3) ŵ = 0.45 mm1
β = 104.580 (14)°T = 200 K
V = 1465.2 (3) Å3Plate, colourless
Z = 40.35 × 0.35 × 0.15 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
2802 independent reflections
Radiation source: Enhance (Mo) X-ray source2159 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.926, Tmax = 0.980k = 127
5638 measured reflectionsl = 1821
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) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0641P)2 + 0.1213P]
where P = (Fo2 + 2Fc2)/3
2802 reflections(Δ/σ)max = 0.002
184 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl40.43514 (6)0.20944 (6)0.30016 (3)0.0438 (2)
Cl50.45031 (7)0.32604 (6)0.47681 (4)0.0495 (2)
O110.82585 (18)0.02229 (15)0.66675 (8)0.0437 (5)
O120.9418 (2)0.12902 (18)0.60850 (10)0.0531 (6)
O210.92748 (19)0.21909 (18)0.47700 (9)0.0508 (6)
O220.7828 (2)0.20048 (17)0.35291 (9)0.0552 (6)
C10.7437 (2)0.01323 (18)0.52381 (11)0.0274 (5)
C20.7347 (2)0.04067 (19)0.44596 (11)0.0280 (6)
C30.6346 (2)0.0214 (2)0.37922 (11)0.0313 (6)
C40.5489 (2)0.1348 (2)0.38645 (11)0.0308 (6)
C50.5570 (2)0.18594 (19)0.46316 (12)0.0310 (6)
C60.6516 (2)0.12484 (19)0.52986 (11)0.0290 (6)
C110.8434 (2)0.0344 (2)0.60563 (11)0.0330 (6)
C210.8196 (2)0.1619 (2)0.42353 (12)0.0362 (7)
N1A0.9508 (2)0.41802 (18)0.32003 (10)0.0332 (5)
C1A1.1027 (3)0.3524 (3)0.32661 (17)0.0586 (9)
C1B0.9510 (3)0.5322 (2)0.37563 (14)0.0499 (8)
C2A1.2148 (3)0.4385 (4)0.30110 (18)0.0765 (13)
C2B0.7912 (4)0.5749 (4)0.3736 (2)0.0921 (14)
H30.625200.015900.326900.0380*
H60.654400.159800.582100.0350*
H120.936 (4)0.167 (3)0.554 (2)0.086*
H1A0.914 (2)0.442 (2)0.2684 (14)0.038 (6)*
H2A0.888 (3)0.349 (3)0.3314 (16)0.060 (8)*
H11A1.146200.324900.383600.0700*
H11B1.007800.609100.359900.0600*
H12A1.086600.269600.293100.0700*
H12B1.004900.505100.431400.0600*
H21A1.231800.520800.334000.0920*
H21B0.718300.506200.345700.1110*
H22A1.175200.462400.243900.0920*
H22B0.768800.661000.344800.1110*
H23A1.312500.389700.308400.0920*
H23B0.780900.585700.429100.1110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl40.0422 (3)0.0457 (3)0.0369 (3)0.0000 (2)0.0024 (2)0.0119 (2)
Cl50.0572 (4)0.0336 (3)0.0569 (4)0.0110 (2)0.0127 (3)0.0009 (2)
O110.0622 (10)0.0417 (9)0.0237 (7)0.0002 (7)0.0043 (6)0.0001 (6)
O120.0602 (11)0.0574 (10)0.0333 (8)0.0215 (9)0.0041 (7)0.0010 (8)
O210.0511 (10)0.0562 (10)0.0402 (9)0.0220 (8)0.0023 (7)0.0072 (8)
O220.0672 (11)0.0540 (10)0.0379 (9)0.0187 (9)0.0010 (8)0.0165 (8)
C10.0282 (10)0.0272 (9)0.0255 (9)0.0089 (8)0.0046 (7)0.0012 (8)
C20.0271 (10)0.0297 (10)0.0273 (9)0.0063 (8)0.0068 (8)0.0024 (8)
C30.0327 (11)0.0362 (11)0.0242 (9)0.0060 (8)0.0057 (8)0.0011 (8)
C40.0287 (10)0.0307 (10)0.0306 (10)0.0044 (8)0.0028 (8)0.0057 (8)
C50.0298 (10)0.0244 (10)0.0390 (11)0.0050 (8)0.0093 (8)0.0014 (8)
C60.0337 (11)0.0269 (10)0.0267 (10)0.0075 (8)0.0080 (8)0.0033 (8)
C110.0381 (11)0.0310 (10)0.0267 (10)0.0080 (9)0.0023 (8)0.0018 (8)
C210.0354 (12)0.0384 (11)0.0341 (11)0.0002 (9)0.0076 (9)0.0033 (9)
N1A0.0431 (10)0.0321 (9)0.0248 (9)0.0045 (8)0.0093 (7)0.0043 (7)
C1A0.0611 (17)0.0593 (16)0.0605 (16)0.0212 (13)0.0251 (13)0.0154 (13)
C1B0.0694 (17)0.0424 (13)0.0364 (12)0.0043 (12)0.0105 (11)0.0094 (10)
C2A0.0464 (16)0.119 (3)0.0653 (18)0.0012 (17)0.0161 (13)0.0123 (18)
C2B0.091 (2)0.093 (3)0.097 (2)0.037 (2)0.0325 (19)0.021 (2)
Geometric parameters (Å, º) top
Cl4—C41.731 (2)C4—C51.388 (3)
Cl5—C51.734 (2)C5—C61.376 (3)
O11—C111.229 (2)C3—H30.9500
O12—C111.279 (3)C6—H60.9500
O21—C211.282 (3)C1A—C2A1.465 (4)
O22—C211.227 (2)C1B—C2B1.485 (5)
O12—H120.99 (3)C1A—H11A0.9900
N1A—C1B1.476 (3)C1A—H12A0.9900
N1A—C1A1.487 (3)C1B—H11B0.9900
N1A—H2A0.94 (3)C1B—H12B0.9900
N1A—H1A0.89 (2)C2A—H21A0.9800
C1—C61.399 (3)C2A—H22A0.9800
C1—C21.415 (3)C2A—H23A0.9800
C1—C111.530 (3)C2B—H21B0.9800
C2—C211.521 (3)C2B—H22B0.9800
C2—C31.402 (3)C2B—H23B0.9800
C3—C41.383 (3)
C11—O12—H12111.7 (19)C4—C3—H3119.00
C1A—N1A—C1B115.69 (19)C1—C6—H6119.00
C1B—N1A—H1A111.8 (13)C5—C6—H6119.00
C1B—N1A—H2A109.3 (17)N1A—C1A—C2A114.0 (2)
H1A—N1A—H2A108 (2)N1A—C1B—C2B111.0 (2)
C1A—N1A—H1A107.2 (13)N1A—C1A—H11A109.00
C1A—N1A—H2A104.6 (18)N1A—C1A—H12A109.00
C6—C1—C11113.33 (16)C2A—C1A—H11A109.00
C2—C1—C6118.18 (17)C2A—C1A—H12A109.00
C2—C1—C11128.49 (16)H11A—C1A—H12A108.00
C1—C2—C21128.33 (17)N1A—C1B—H11B109.00
C1—C2—C3118.09 (17)N1A—C1B—H12B109.00
C3—C2—C21113.58 (16)C2B—C1B—H11B109.00
C2—C3—C4122.65 (17)C2B—C1B—H12B110.00
Cl4—C4—C5121.73 (15)H11B—C1B—H12B108.00
C3—C4—C5118.81 (17)C1A—C2A—H21A109.00
Cl4—C4—C3119.47 (14)C1A—C2A—H22A109.00
Cl5—C5—C4121.26 (15)C1A—C2A—H23A109.00
Cl5—C5—C6119.11 (15)H21A—C2A—H22A110.00
C4—C5—C6119.63 (17)H21A—C2A—H23A109.00
C1—C6—C5122.58 (17)H22A—C2A—H23A109.00
O11—C11—O12122.44 (18)C1B—C2B—H21B110.00
O11—C11—C1117.61 (17)C1B—C2B—H22B110.00
O12—C11—C1119.95 (17)C1B—C2B—H23B109.00
O21—C21—O22121.95 (19)H21B—C2B—H22B109.00
O22—C21—C2117.71 (18)H21B—C2B—H23B109.00
O21—C21—C2120.33 (17)H22B—C2B—H23B109.00
C2—C3—H3119.00
C1A—N1A—C1B—C2B170.6 (2)C1—C2—C21—O22172.41 (19)
C1B—N1A—C1A—C2A67.1 (3)C21—C2—C3—C4178.72 (17)
C6—C1—C2—C21178.71 (18)C3—C2—C21—O226.7 (3)
C6—C1—C2—C30.4 (3)C3—C2—C21—O21172.07 (18)
C2—C1—C6—C52.0 (3)C1—C2—C3—C42.1 (3)
C11—C1—C6—C5177.95 (17)C2—C3—C4—Cl4176.95 (15)
C2—C1—C11—O11175.50 (19)C2—C3—C4—C52.9 (3)
C2—C1—C11—O125.3 (3)Cl4—C4—C5—C6178.62 (15)
C6—C1—C11—O114.6 (3)C3—C4—C5—Cl5178.93 (15)
C11—C1—C2—C3179.57 (18)Cl4—C4—C5—Cl51.2 (2)
C11—C1—C2—C211.3 (3)C3—C4—C5—C61.2 (3)
C6—C1—C11—O12174.69 (18)C4—C5—C6—C11.2 (3)
C1—C2—C21—O218.8 (3)Cl5—C5—C6—C1178.64 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O11i0.89 (2)1.89 (2)2.772 (2)169.6 (19)
N1A—H2A···O220.94 (3)1.83 (3)2.765 (3)173 (3)
O12—H12···O210.99 (3)1.40 (3)2.388 (2)179 (4)
C3—H3···O220.952.282.663 (3)103
C6—H6···O110.952.282.662 (2)103
Symmetry code: (i) x, y+1/2, z1/2.
(III) bis(butanaminium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate top
Crystal data top
2C4H12N+·C8H2Cl2O42·H2OZ = 2
Mr = 399.30F(000) = 424
Triclinic, P1Dx = 1.253 Mg m3
Hall symbol: -P 1Melting point: 457 K
a = 8.1362 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3043 (11) ÅCell parameters from 6406 reflections
c = 15.406 (1) Åθ = 3.0–32.5°
α = 78.678 (7)°µ = 0.33 mm1
β = 85.846 (6)°T = 200 K
γ = 67.777 (9)°Prism, colourless
V = 1058.62 (18) Å30.55 × 0.30 × 0.20 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
4851 independent reflections
Radiation source: Enhance (Mo) X-ray source3858 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 16.077 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.865, Tmax = 0.940l = 1919
15869 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.18 w = 1/[σ2(Fo2) + (0.0837P)2 + 0.0287P]
where P = (Fo2 + 2Fc2)/3
4851 reflections(Δ/σ)max = 0.001
260 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1A0.83030 (18)0.40803 (16)0.43961 (9)0.0301 (4)
C2A0.8506 (2)0.53396 (18)0.36814 (11)0.0363 (5)
C3A0.8949 (3)0.4766 (2)0.28024 (13)0.0498 (6)
C4A0.8915 (3)0.6078 (3)0.20387 (16)0.0660 (8)
C5A0.7110 (4)0.7306 (3)0.18164 (17)0.0741 (9)
N1B0.32948 (19)0.11939 (16)0.40526 (10)0.0331 (4)
C2B0.1554 (2)0.0456 (2)0.35886 (13)0.0438 (6)
C3B0.1793 (2)0.0228 (2)0.25901 (13)0.0482 (6)
C4B0.0032 (3)0.0372 (3)0.21012 (16)0.0626 (8)
C5B0.0245 (5)0.0527 (5)0.1113 (2)0.1087 (13)
Cl40.46735 (10)0.17647 (7)0.03754 (3)0.0717 (2)
Cl50.26463 (8)0.54775 (7)0.02437 (3)0.0627 (2)
O110.45042 (17)0.59391 (14)0.35104 (9)0.0444 (4)
O120.31110 (18)0.43995 (16)0.41980 (9)0.0493 (5)
O210.68790 (15)0.18640 (13)0.41153 (7)0.0364 (4)
O220.61194 (15)0.00555 (12)0.38236 (8)0.0351 (3)
C10.42808 (18)0.40301 (16)0.27681 (10)0.0254 (4)
C20.51625 (18)0.23900 (16)0.28276 (10)0.0257 (4)
C30.5259 (2)0.17325 (18)0.20775 (11)0.0340 (5)
C40.4510 (2)0.2661 (2)0.12824 (11)0.0405 (5)
C50.3648 (2)0.4280 (2)0.12225 (11)0.0392 (5)
C60.3565 (2)0.49536 (18)0.19618 (11)0.0330 (5)
C110.39599 (18)0.48459 (16)0.35637 (10)0.0270 (4)
C210.61058 (18)0.13221 (16)0.36576 (10)0.0256 (4)
O1W0.18354 (16)0.20557 (14)0.47498 (9)0.0410 (4)
H11A0.781 (3)0.447 (2)0.4846 (15)0.048 (6)*
H12A0.936 (3)0.329 (2)0.4554 (12)0.035 (5)*
H13A0.763 (3)0.357 (2)0.4210 (13)0.041 (5)*
H21A0.946500.565000.384300.0430*
H22A0.739000.628100.362100.0430*
H31A1.014400.391800.284200.0600*
H32A0.808400.431200.268600.0600*
H41A0.969500.659500.218500.0790*
H42A0.941300.560800.150900.0790*
H51A0.719900.812500.132900.0890*
H52A0.660300.778100.233600.0890*
H53A0.634200.681700.163900.0890*
H11B0.398 (3)0.064 (2)0.3886 (14)0.046 (5)*
H12B0.315 (3)0.126 (2)0.4632 (17)0.049 (6)*
H13B0.380 (3)0.216 (3)0.3920 (13)0.043 (5)*
H21B0.088300.058000.376100.0530*
H22B0.085600.113600.377100.0530*
H31B0.257200.124600.242600.0580*
H32B0.238700.053600.240400.0580*
H41B0.058900.036300.231400.0750*
H42B0.072000.141500.224400.0750*
H51B0.090800.079000.084000.1300*
H52B0.108300.047500.096900.1300*
H53B0.069900.136600.088600.1300*
H30.585000.062500.211300.0410*
H60.300800.606600.191400.0400*
H11W0.233 (3)0.276 (3)0.4557 (14)0.051 (6)*
H12W0.242 (4)0.153 (3)0.5268 (19)0.078 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0276 (7)0.0331 (7)0.0318 (7)0.0118 (6)0.0005 (5)0.0098 (5)
C2A0.0328 (8)0.0327 (8)0.0402 (9)0.0102 (6)0.0000 (7)0.0037 (6)
C3A0.0480 (11)0.0480 (10)0.0435 (11)0.0085 (8)0.0091 (8)0.0083 (8)
C4A0.0640 (14)0.0732 (15)0.0523 (14)0.0219 (12)0.0087 (11)0.0025 (11)
C5A0.0809 (17)0.0767 (16)0.0498 (14)0.0204 (13)0.0099 (12)0.0075 (11)
N1B0.0381 (7)0.0303 (7)0.0348 (8)0.0149 (6)0.0019 (6)0.0100 (6)
C2B0.0365 (9)0.0495 (10)0.0476 (11)0.0122 (8)0.0053 (8)0.0199 (8)
C3B0.0392 (10)0.0500 (10)0.0496 (12)0.0116 (8)0.0055 (8)0.0039 (8)
C4B0.0576 (13)0.0642 (13)0.0617 (14)0.0125 (11)0.0184 (10)0.0160 (10)
C5B0.091 (2)0.148 (3)0.0578 (18)0.014 (2)0.0309 (16)0.0031 (18)
Cl40.1103 (5)0.0770 (4)0.0354 (3)0.0340 (4)0.0094 (3)0.0258 (2)
Cl50.0678 (4)0.0743 (4)0.0323 (3)0.0172 (3)0.0134 (2)0.0077 (2)
O110.0576 (8)0.0330 (6)0.0521 (8)0.0238 (6)0.0047 (6)0.0168 (5)
O120.0630 (8)0.0618 (8)0.0433 (8)0.0404 (7)0.0230 (6)0.0288 (6)
O210.0452 (7)0.0362 (6)0.0348 (6)0.0223 (5)0.0114 (5)0.0037 (4)
O220.0389 (6)0.0251 (5)0.0421 (7)0.0125 (5)0.0086 (5)0.0037 (4)
C10.0215 (6)0.0275 (7)0.0290 (8)0.0106 (5)0.0006 (5)0.0067 (5)
C20.0248 (7)0.0274 (7)0.0287 (8)0.0126 (6)0.0006 (5)0.0080 (5)
C30.0403 (9)0.0336 (8)0.0327 (9)0.0158 (7)0.0007 (7)0.0128 (6)
C40.0491 (10)0.0510 (10)0.0273 (8)0.0221 (8)0.0011 (7)0.0130 (7)
C50.0398 (9)0.0482 (10)0.0282 (9)0.0171 (7)0.0040 (7)0.0007 (7)
C60.0305 (8)0.0321 (8)0.0347 (9)0.0118 (6)0.0009 (6)0.0024 (6)
C110.0218 (6)0.0241 (7)0.0335 (8)0.0051 (5)0.0022 (6)0.0080 (5)
C210.0229 (7)0.0258 (7)0.0292 (8)0.0085 (5)0.0017 (5)0.0096 (5)
O1W0.0353 (6)0.0332 (6)0.0526 (8)0.0114 (5)0.0122 (6)0.0019 (5)
Geometric parameters (Å, º) top
Cl4—C41.7356 (18)C5A—H51A0.9800
Cl5—C51.7352 (18)C5A—H52A0.9800
O11—C111.241 (2)C5A—H53A0.9800
O12—C111.251 (2)C2B—C3B1.520 (3)
O21—C211.2613 (19)C3B—C4B1.523 (3)
O22—C211.2528 (18)C4B—C5B1.504 (4)
O1W—H11W0.89 (3)C2B—H22B0.9900
O1W—H12W0.91 (3)C2B—H21B0.9900
N1A—C2A1.492 (2)C3B—H32B0.9900
N1A—H13A0.94 (2)C3B—H31B0.9900
N1A—H12A0.91 (2)C4B—H42B0.9900
N1A—H11A0.85 (2)C4B—H41B0.9900
N1B—C2B1.486 (2)C5B—H53B0.9800
N1B—H12B0.89 (3)C5B—H52B0.9800
N1B—H13B0.89 (3)C5B—H51B0.9800
N1B—H11B0.89 (2)C1—C111.522 (2)
C2A—C3A1.522 (3)C1—C21.407 (2)
C3A—C4A1.513 (3)C1—C61.388 (2)
C4A—C5A1.493 (4)C2—C211.509 (2)
C2A—H21A0.9900C2—C31.394 (2)
C2A—H22A0.9900C3—C41.383 (2)
C3A—H32A0.9900C4—C51.388 (2)
C3A—H31A0.9900C5—C61.390 (2)
C4A—H42A0.9900C3—H30.9500
C4A—H41A0.9900C6—H60.9500
H11W—O1W—H12W103 (2)H21B—C2B—H22B108.00
H12A—N1A—H13A103.8 (18)N1B—C2B—H21B109.00
C2A—N1A—H13A112.1 (12)C2B—C3B—H31B109.00
H11A—N1A—H13A109 (2)C2B—C3B—H32B109.00
C2A—N1A—H12A111.8 (13)C4B—C3B—H32B109.00
C2A—N1A—H11A110.2 (13)H31B—C3B—H32B108.00
H11A—N1A—H12A109.8 (19)C4B—C3B—H31B109.00
C2B—N1B—H11B112.0 (14)C3B—C4B—H41B109.00
H11B—N1B—H13B111 (2)C5B—C4B—H41B109.00
H12B—N1B—H13B110.1 (17)C5B—C4B—H42B109.00
C2B—N1B—H13B106.0 (16)C3B—C4B—H42B109.00
C2B—N1B—H12B110.8 (16)H41B—C4B—H42B108.00
H11B—N1B—H12B107 (2)C4B—C5B—H52B109.00
N1A—C2A—C3A110.92 (13)C4B—C5B—H53B109.00
C2A—C3A—C4A112.32 (16)H51B—C5B—H52B109.00
C3A—C4A—C5A114.3 (2)H51B—C5B—H53B109.00
N1A—C2A—H22A109.00H52B—C5B—H53B109.00
H21A—C2A—H22A108.00C4B—C5B—H51B109.00
C3A—C2A—H21A109.00C2—C1—C6119.26 (14)
N1A—C2A—H21A109.00C2—C1—C11123.08 (13)
C3A—C2A—H22A109.00C6—C1—C11117.54 (13)
C4A—C3A—H32A109.00C1—C2—C21122.55 (13)
C2A—C3A—H31A109.00C3—C2—C21118.43 (13)
C4A—C3A—H31A109.00C1—C2—C3118.92 (14)
H31A—C3A—H32A108.00C2—C3—C4121.28 (15)
C2A—C3A—H32A109.00Cl4—C4—C3118.88 (13)
H41A—C4A—H42A108.00Cl4—C4—C5121.31 (13)
C5A—C4A—H41A109.00C3—C4—C5119.81 (15)
C3A—C4A—H41A109.00Cl5—C5—C6119.35 (13)
C3A—C4A—H42A109.00C4—C5—C6119.50 (15)
C5A—C4A—H42A109.00Cl5—C5—C4121.14 (13)
C4A—C5A—H51A109.00C1—C6—C5121.20 (15)
C4A—C5A—H52A109.00O11—C11—C1116.95 (14)
C4A—C5A—H53A109.00O12—C11—C1117.25 (14)
H51A—C5A—H52A109.00O11—C11—O12125.74 (15)
H51A—C5A—H53A110.00O21—C21—C2117.53 (13)
H52A—C5A—H53A109.00O22—C21—C2117.62 (14)
N1B—C2B—C3B111.23 (15)O21—C21—O22124.80 (14)
C2B—C3B—C4B112.19 (16)C2—C3—H3119.00
C3B—C4B—C5B113.1 (2)C4—C3—H3119.00
N1B—C2B—H22B109.00C1—C6—H6119.00
C3B—C2B—H21B109.00C5—C6—H6119.00
C3B—C2B—H22B109.00
N1A—C2A—C3A—C4A172.11 (18)C1—C2—C3—C40.1 (3)
C2A—C3A—C4A—C5A68.3 (3)C21—C2—C3—C4176.29 (15)
N1B—C2B—C3B—C4B174.22 (16)C1—C2—C21—O2135.3 (2)
C2B—C3B—C4B—C5B177.1 (2)C1—C2—C21—O22147.30 (15)
C6—C1—C2—C31.4 (2)C3—C2—C21—O21140.96 (16)
C6—C1—C2—C21174.86 (15)C3—C2—C21—O2236.4 (2)
C11—C1—C2—C3174.49 (15)C2—C3—C4—Cl4179.82 (14)
C11—C1—C2—C219.3 (2)C2—C3—C4—C50.2 (3)
C2—C1—C6—C52.4 (3)Cl4—C4—C5—Cl51.6 (2)
C11—C1—C6—C5173.73 (15)Cl4—C4—C5—C6179.23 (14)
C2—C1—C11—O11125.03 (17)C3—C4—C5—Cl5178.45 (14)
C2—C1—C11—O1257.7 (2)C3—C4—C5—C60.7 (3)
C6—C1—C11—O1159.0 (2)Cl5—C5—C6—C1177.15 (13)
C6—C1—C11—O12118.20 (17)C4—C5—C6—C12.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O12i0.85 (2)1.92 (2)2.762 (2)170 (2)
N1A—H12A···O1Wii0.91 (2)1.92 (2)2.799 (2)164 (2)
N1A—H13A···O210.94 (2)1.94 (2)2.831 (2)158.4 (17)
N1B—H11B···O220.89 (2)2.00 (3)2.847 (2)158.9 (19)
N1B—H12B···O21iii0.89 (3)1.90 (3)2.7737 (19)167.9 (17)
N1B—H13B···O11iv0.89 (3)1.86 (3)2.7481 (19)170 (2)
O1W—H11W···O120.89 (3)1.84 (3)2.723 (2)173 (2)
O1W—H12W···O22iii0.91 (3)1.87 (3)2.7648 (18)166 (3)
C2B—H21B···O1W0.992.573.289 (2)130
C2A—H22A···O110.992.513.110 (2)119
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x, y1, z.
(IV) bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate top
Crystal data top
2C5H12N+·C8H2Cl2O42·H2OF(000) = 896
Mr = 423.32Dx = 1.332 Mg m3
Monoclinic, P21/cMelting point: 405 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.8481 (10) ÅCell parameters from 6842 reflections
b = 10.5937 (8) Åθ = 3.4–28.8°
c = 14.6129 (10) ŵ = 0.34 mm1
β = 99.903 (7)°T = 200 K
V = 2111.8 (3) Å3Plate, colourless
Z = 40.35 × 0.20 × 0.18 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
4805 independent reflections
Radiation source: Enhance (Mo) X-ray source3570 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 16.077 pixels mm-1θmax = 27.5°, θmin = 3.4°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.701, Tmax = 0.980l = 1818
26626 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0644P)2]
where P = (Fo2 + 2Fc2)/3
4805 reflections(Δ/σ)max < 0.001
268 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1A0.06019 (10)0.62705 (12)0.30611 (8)0.0248 (4)
C2A0.08561 (12)0.59975 (16)0.40785 (10)0.0342 (5)
C3A0.19204 (12)0.55895 (17)0.43278 (11)0.0389 (5)
C4A0.21235 (12)0.44461 (15)0.37525 (11)0.0360 (5)
C5A0.18615 (12)0.47509 (15)0.27239 (11)0.0345 (5)
C6A0.07982 (12)0.51771 (15)0.24770 (11)0.0336 (5)
N1B0.18744 (9)0.53788 (12)0.07825 (9)0.0259 (4)
C2B0.17157 (12)0.47472 (15)0.00943 (11)0.0331 (5)
C3B0.25761 (14)0.39003 (16)0.04612 (12)0.0422 (6)
C4B0.35296 (14)0.46454 (18)0.06222 (13)0.0497 (6)
C5B0.36718 (13)0.53043 (18)0.02755 (13)0.0450 (6)
C6B0.27991 (11)0.61271 (14)0.06581 (11)0.0307 (5)
Cl40.54291 (3)1.11882 (5)0.10952 (4)0.0515 (2)
Cl50.54725 (3)0.83387 (4)0.18411 (4)0.0524 (2)
O110.18070 (8)0.83778 (9)0.29506 (7)0.0299 (3)
O120.11586 (8)0.85918 (11)0.14445 (8)0.0389 (4)
O210.13624 (7)1.13683 (10)0.22891 (7)0.0297 (3)
O220.15811 (8)1.22425 (10)0.09345 (7)0.0358 (3)
C10.27323 (10)0.94353 (13)0.19485 (9)0.0210 (4)
C20.27163 (10)1.06951 (13)0.16393 (9)0.0210 (4)
C30.35526 (11)1.12116 (14)0.13754 (10)0.0268 (4)
C40.44021 (11)1.05035 (15)0.14302 (11)0.0305 (4)
C50.44221 (11)0.92640 (15)0.17569 (11)0.0301 (4)
C60.35922 (11)0.87368 (14)0.20170 (10)0.0269 (4)
C110.18131 (10)0.87618 (13)0.21301 (10)0.0232 (4)
C210.18026 (10)1.15032 (12)0.16064 (10)0.0231 (4)
O1W0.03247 (9)0.70087 (11)0.06512 (9)0.0373 (4)
H11A0.0042 (15)0.6453 (17)0.2911 (12)0.044 (5)*
H12A0.0983 (13)0.6934 (18)0.2940 (12)0.047 (5)*
H21A0.042500.532000.424500.0410*
H22A0.074700.676300.443600.0410*
H31A0.207100.537400.499600.0470*
H32A0.235200.629600.421300.0470*
H41A0.282500.421500.390700.0430*
H42A0.173100.371800.390200.0430*
H51A0.196300.399300.235500.0410*
H52A0.229800.542700.256500.0410*
H61A0.065400.542000.181300.0400*
H62A0.036000.446800.257200.0400*
H11B0.1854 (13)0.4805 (16)0.1236 (12)0.039 (5)*
H12B0.1311 (14)0.5936 (17)0.0945 (12)0.044 (5)*
H21B0.110700.424000.002700.0400*
H22B0.163900.539400.056600.0400*
H31B0.262000.321500.001000.0510*
H32B0.247300.351000.105200.0510*
H41B0.408700.406800.083000.0600*
H42B0.351200.528200.111500.0600*
H51B0.427000.583200.015400.0540*
H52B0.376500.466100.074400.0540*
H61B0.275400.683600.022600.0370*
H62B0.289000.648600.126300.0370*
H30.354001.205700.115600.0320*
H60.361200.789500.224300.0320*
H11W0.0098 (15)0.749 (2)0.0907 (14)0.058 (6)*
H12W0.0602 (15)0.733 (2)0.0152 (15)0.062 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0213 (6)0.0236 (6)0.0299 (7)0.0011 (5)0.0052 (5)0.0039 (5)
C2A0.0371 (9)0.0404 (9)0.0275 (8)0.0061 (7)0.0125 (7)0.0033 (7)
C3A0.0399 (10)0.0512 (10)0.0245 (8)0.0100 (8)0.0024 (7)0.0046 (7)
C4A0.0330 (9)0.0295 (8)0.0462 (10)0.0073 (7)0.0091 (8)0.0095 (7)
C5A0.0378 (9)0.0297 (8)0.0379 (9)0.0027 (7)0.0117 (7)0.0075 (7)
C6A0.0375 (9)0.0314 (8)0.0307 (8)0.0028 (7)0.0025 (7)0.0055 (7)
N1B0.0287 (7)0.0250 (6)0.0233 (6)0.0024 (5)0.0022 (5)0.0025 (5)
C2B0.0396 (9)0.0299 (8)0.0311 (8)0.0024 (7)0.0102 (7)0.0005 (7)
C3B0.0607 (12)0.0288 (9)0.0369 (9)0.0078 (8)0.0078 (8)0.0084 (7)
C4B0.0457 (11)0.0503 (11)0.0469 (11)0.0139 (9)0.0094 (9)0.0086 (9)
C5B0.0278 (9)0.0525 (11)0.0531 (11)0.0037 (8)0.0021 (8)0.0069 (9)
C6B0.0323 (8)0.0286 (8)0.0302 (8)0.0032 (6)0.0026 (7)0.0034 (6)
Cl40.0308 (2)0.0537 (3)0.0743 (3)0.0102 (2)0.0215 (2)0.0062 (2)
Cl50.0289 (2)0.0503 (3)0.0797 (4)0.0127 (2)0.0138 (2)0.0071 (2)
O110.0381 (6)0.0253 (5)0.0275 (6)0.0063 (5)0.0090 (5)0.0026 (4)
O120.0322 (6)0.0507 (7)0.0315 (6)0.0181 (5)0.0007 (5)0.0057 (5)
O210.0250 (5)0.0354 (6)0.0286 (6)0.0035 (4)0.0047 (4)0.0006 (5)
O220.0364 (6)0.0337 (6)0.0352 (6)0.0048 (5)0.0001 (5)0.0126 (5)
C10.0239 (7)0.0227 (7)0.0157 (6)0.0034 (5)0.0017 (5)0.0030 (5)
C20.0216 (7)0.0237 (7)0.0164 (6)0.0028 (5)0.0001 (5)0.0020 (5)
C30.0261 (8)0.0264 (7)0.0270 (8)0.0045 (6)0.0024 (6)0.0027 (6)
C40.0228 (7)0.0349 (8)0.0347 (8)0.0079 (6)0.0074 (6)0.0007 (7)
C50.0220 (7)0.0327 (8)0.0352 (8)0.0031 (6)0.0040 (6)0.0019 (7)
C60.0281 (8)0.0232 (7)0.0283 (8)0.0003 (6)0.0014 (6)0.0004 (6)
C110.0263 (7)0.0180 (7)0.0263 (7)0.0016 (5)0.0075 (6)0.0040 (6)
C210.0222 (7)0.0209 (7)0.0240 (7)0.0040 (5)0.0019 (6)0.0029 (6)
O1W0.0325 (6)0.0351 (7)0.0400 (7)0.0093 (5)0.0061 (6)0.0099 (5)
Geometric parameters (Å, º) top
Cl4—C41.7401 (16)C5A—H52A0.9900
Cl5—C51.7408 (16)C6A—H62A0.9900
O11—C111.2675 (18)C6A—H61A0.9900
O12—C111.2431 (18)C2B—C3B1.514 (2)
O21—C211.2635 (17)C3B—C4B1.522 (3)
O22—C211.2522 (17)C4B—C5B1.528 (3)
O1W—H11W0.82 (2)C5B—C6B1.517 (2)
O1W—H12W0.84 (2)C2B—H21B0.9900
N1A—C6A1.491 (2)C2B—H22B0.9900
N1A—C2A1.4960 (19)C3B—H31B0.9900
N1A—H11A0.90 (2)C3B—H32B0.9900
N1A—H12A0.914 (19)C4B—H41B0.9900
N1B—C6B1.490 (2)C4B—H42B0.9900
N1B—C2B1.495 (2)C5B—H52B0.9900
N1B—H12B0.975 (19)C5B—H51B0.9900
N1B—H11B0.896 (17)C6B—H62B0.9900
C2A—C3A1.519 (2)C6B—H61B0.9900
C3A—C4A1.528 (2)C1—C111.522 (2)
C4A—C5A1.519 (2)C1—C21.4080 (19)
C5A—C6A1.523 (2)C1—C61.391 (2)
C2A—H22A0.9900C2—C211.522 (2)
C2A—H21A0.9900C2—C31.394 (2)
C3A—H31A0.9900C3—C41.386 (2)
C3A—H32A0.9900C4—C51.396 (2)
C4A—H41A0.9900C5—C61.388 (2)
C4A—H42A0.9900C3—H30.9500
C5A—H51A0.9900C6—H60.9500
H11W—O1W—H12W109 (2)C3B—C2B—H21B110.00
C2A—N1A—C6A112.57 (12)N1B—C2B—H21B110.00
C6A—N1A—H11A107.3 (11)H21B—C2B—H22B108.00
H11A—N1A—H12A111.6 (16)C3B—C2B—H22B110.00
C2A—N1A—H12A107.2 (11)C2B—C3B—H32B109.00
C2A—N1A—H11A109.7 (11)C4B—C3B—H31B109.00
C6A—N1A—H12A108.6 (11)C2B—C3B—H31B109.00
C2B—N1B—C6B112.55 (12)H31B—C3B—H32B108.00
C2B—N1B—H11B109.9 (11)C4B—C3B—H32B109.00
H11B—N1B—H12B108.0 (15)C3B—C4B—H41B110.00
C6B—N1B—H11B111.6 (12)C5B—C4B—H41B110.00
C6B—N1B—H12B110.0 (11)C5B—C4B—H42B110.00
C2B—N1B—H12B104.5 (11)H41B—C4B—H42B108.00
N1A—C2A—C3A110.25 (13)C3B—C4B—H42B110.00
C2A—C3A—C4A110.88 (13)C4B—C5B—H52B109.00
C3A—C4A—C5A109.92 (13)C6B—C5B—H51B109.00
C4A—C5A—C6A110.74 (13)C4B—C5B—H51B109.00
N1A—C6A—C5A111.02 (13)H51B—C5B—H52B108.00
H21A—C2A—H22A108.00C6B—C5B—H52B109.00
N1A—C2A—H21A110.00N1B—C6B—H62B110.00
C3A—C2A—H21A110.00C5B—C6B—H61B110.00
C3A—C2A—H22A110.00C5B—C6B—H62B110.00
N1A—C2A—H22A110.00H61B—C6B—H62B108.00
C2A—C3A—H32A109.00N1B—C6B—H61B110.00
C2A—C3A—H31A109.00C2—C1—C6119.57 (13)
C4A—C3A—H32A109.00C2—C1—C11122.20 (12)
C4A—C3A—H31A109.00C6—C1—C11118.00 (12)
H31A—C3A—H32A108.00C1—C2—C21120.70 (12)
H41A—C4A—H42A108.00C3—C2—C21119.76 (12)
C3A—C4A—H42A110.00C1—C2—C3119.53 (13)
C5A—C4A—H41A110.00C2—C3—C4120.59 (14)
C5A—C4A—H42A110.00Cl4—C4—C3119.00 (12)
C3A—C4A—H41A110.00Cl4—C4—C5121.28 (12)
C4A—C5A—H52A110.00C3—C4—C5119.71 (14)
C6A—C5A—H52A110.00Cl5—C5—C6118.37 (12)
H51A—C5A—H52A108.00C4—C5—C6120.23 (14)
C4A—C5A—H51A110.00Cl5—C5—C4121.41 (12)
C6A—C5A—H51A109.00C1—C6—C5120.34 (14)
N1A—C6A—H62A109.00O11—C11—C1117.21 (12)
N1A—C6A—H61A109.00O12—C11—C1116.31 (12)
C5A—C6A—H62A109.00O11—C11—O12126.39 (14)
C5A—C6A—H61A109.00O21—C21—C2115.02 (12)
H61A—C6A—H62A108.00O22—C21—C2117.83 (12)
N1B—C2B—C3B110.24 (13)O21—C21—O22127.12 (13)
C2B—C3B—C4B110.89 (14)C2—C3—H3120.00
C3B—C4B—C5B109.92 (15)C4—C3—H3120.00
C4B—C5B—C6B111.52 (15)C1—C6—H6120.00
N1B—C6B—C5B110.65 (13)C5—C6—H6120.00
N1B—C2B—H22B110.00
C6A—N1A—C2A—C3A56.24 (17)C2—C1—C11—O11118.74 (15)
C2A—N1A—C6A—C5A55.92 (17)C2—C1—C11—O1264.50 (18)
C6B—N1B—C2B—C3B57.31 (16)C6—C1—C11—O1166.86 (17)
C2B—N1B—C6B—C5B56.01 (17)C6—C1—C11—O12109.90 (15)
N1A—C2A—C3A—C4A56.58 (17)C1—C2—C3—C41.1 (2)
C2A—C3A—C4A—C5A57.19 (18)C21—C2—C3—C4177.83 (13)
C3A—C4A—C5A—C6A56.35 (17)C1—C2—C21—O2140.40 (18)
C4A—C5A—C6A—N1A55.68 (17)C1—C2—C21—O22141.41 (13)
N1B—C2B—C3B—C4B57.22 (18)C3—C2—C21—O21138.54 (13)
C2B—C3B—C4B—C5B56.38 (19)C3—C2—C21—O2239.65 (19)
C3B—C4B—C5B—C6B55.2 (2)C2—C3—C4—Cl4179.89 (11)
C4B—C5B—C6B—N1B54.75 (18)C2—C3—C4—C50.3 (2)
C6—C1—C2—C32.2 (2)Cl4—C4—C5—Cl50.3 (2)
C6—C1—C2—C21176.73 (13)Cl4—C4—C5—C6179.77 (12)
C11—C1—C2—C3172.11 (13)C3—C4—C5—Cl5179.84 (12)
C11—C1—C2—C218.95 (19)C3—C4—C5—C60.7 (2)
C2—C1—C6—C51.9 (2)Cl5—C5—C6—C1179.07 (11)
C11—C1—C6—C5172.68 (13)C4—C5—C6—C10.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O21i0.90 (2)1.80 (2)2.6820 (17)164.0 (17)
N1A—H12A···O110.914 (19)1.907 (19)2.8085 (17)168.4 (16)
N1B—H11B···O11i0.896 (17)1.917 (17)2.8054 (16)170.7 (16)
N1B—H12B···O1W0.975 (19)1.882 (19)2.7866 (18)153.1 (15)
O1W—H11W···O120.82 (2)1.93 (2)2.7490 (17)176 (2)
O1W—H12W···O22ii0.84 (2)1.96 (2)2.7639 (17)162 (2)
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+2, z.
Table 5. Comparative structural parameters (Å, °) and structural classification for the series of 'planar' 1:1 DCPA salts of the named Lewis base types top
Lewis base typestructure type**C1–C11C2–C21C1–C2–C21C2–C1–C11O12–H···O21C1–C2–C21–O22C2–C1–C11–O11
TEAa01.5366 (19)1.5344 (19)128.16 (11)129.73 (11)2.4223 (14)178.46 (13)179.64 (13)
DEAa21.531 (3)1.521 (3)128.33 (17)128.49 (16)2.388 (2)-172.41 (19)175.50 (19)
IPAb11.5189 (18)1.5297 (18)128.32 (11)128.14 (11)2.4507 (16)161.01 (13)-156.69 (13)
DIPAc11.523 (3)1.516 (3)128.5 (2)128.2 (2)2.381 (3)-170.8 (2)-176.7 (2)
HMTc11.529 (9)1.523 (8)129.3 (5)127.8 (5)2.381 (8)-173.7 (6)173.6 (5)
INIPAd11.522 (4)1.534 (4)128.8 (2)128.2 (2)2.392 (3)-174.6 (3)174.2 (3)
TMAe11.528 (3)1.529 (3)128.9 (2)128.9 (2)2.380 (3)180180
TBAf01.523 (13)1.529 (14)128.3 (9)128.9 (8)2.34 (1)173 (1)168 (1)
BRUg01.523 (3)1.535 (3)128.9 (2)128.4 (2)2.441 (3)-177.8 (2)163.9 (2)
NICAh01.531 (3)1.528 (3)127.88 (16)128.93 (16)2.410 (2)172.58 (18)-178.68 (19)
INICAh11.521 (8)1.515 (11)128.3 (5)128.0 (5)2.393 (8)-178.6 (7)173.0 (7)
AMPMh01.527 (2)1.532 (2)128.72 (14)128.90 (14)2.4037 (19)-179.70 (16)-170.16 (16)
PMPYi11.527 (5)1.531 (5)128.9 (3)128.8 (3)2.376 (4)169.9 (3)-173.2 (3)
TFMANj21.5161 (19)1.520 (2)128.35 (13)128.69 (12)2.3908 (17)-179.04 (16)179.50 (16)
8-AQk11.525 (2)1.534 (2)129.27 (14)128.36 (14)2.3922 (18)-175.88 (15)174.38 (15)
8-HQk11.527 (3)1.518 (3)127.97 (19)128.88 (19)2.389 (2)-176.6 (2)171.3 (2)
BTMAPl01.536 (2)1.534 (2)129.09 (15)129.00 (14)2.4004 (19)172.41 (15)179.32 (16)
PHENm01.538 (2)1.536 (3)128.55 (15)129.18 (16)2.4054 (19)-179.53 (16)-168.30 (16)
QACn*21.527 (7)1.527 (7)129.6 (5)128.4 (4)2.366 (7)177.0 (5)-172.4 (5)
QACn*21.522 (8)1.511 (6)128.2 (4)129.0 (4)2.377 (5)178.5 (5)-174.2 (5)
(a) this work [TEA is triethylamine, DEA is diethylamine]; (b) Smith & Wermuth (2010b) [IPA is isopropylamine]; (c) Smith & Wermuth (2010a) [DIPA is diisopropylamine, HMT is hexamethylenetetramine]; (d) Smith & Wermuth (2010e) [INIPA is isonipecotamide]; (e) Bozkurt et al. (2006) [TMA is tetramethylammonium ion]; (f) Mattes & Dorau (1986) [TBA is tetra(n-butyl)ammonium ion]; (g) Smith et al. (2007) [BRU is brucine]; (h) Smith et al. (2009a) [NICA is nicotinamide, INICA is isonicotinamide, AMPM is 2-aminopyrimidine]; (i) Smith & Wermuth (2010d) [PMPY is 4-methylpyridine]; (j) Odabaşoğlu & Büyükgüngör (2007) [TFMAN is 3-(trifluoromethyl)aniline]; (k) Smith et al. (2008b) [8-AQ is 8-aminoquinoline, 8-HQ is 8-hydroxyquinoline]; (l) Mallinson et al. (2003); Parkin et al. (2007) [BTMAP is 1,8-bis(trimethylamino)naphthalene]; (m) Smith et al. (2009c) [PHEN is 1,10-phenanthroline]; (n) Smith et al. (2009) [QAC is quinacrine]; (*) For the quinacrine salt, there are two independent DCPA anions in the asymmetric unit; (**) 0 = zero-dimensional; 1 = one-dimensional; 2 = two-dimensional.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds