Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002419/qb0184sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002419/qb0184Isup2.hkl |
CCDC reference: 143341
Dicyclohexylamine, adipic acid and bis(tributyltin) oxide in a 2:2:1 molar stoichiometry was heated in a small volume of ethanol in an attempt to synthesize dicyclohexylammonium succinatotributylstannate. The procedure had been used to prepare the tributylstannate derivatives of oxalic (Ng et al., 1990), malonic (Ng et al., 1992) and succinic (Ng & Holecek, 1998) acids, but the reaction with adipic acid gave the organic salt as a hydrate. The Cu radiation powder diffractogram of the bulk compound is identical to the diffractogram that is calculated from the atomic coordinates by POWDIS (McArdle & Cunningham, 1998).
Data collection: XSCANS (Siemens, 1990); cell refinement: XSCANS; data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
2C12H24N+·C6H8O42−·H2O | F(000) = 1168 |
Mr = 526.78 | Dx = 1.132 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.155 (3) Å | Cell parameters from 25 reflections |
b = 15.638 (5) Å | θ = 7.0–14.0° |
c = 20.102 (6) Å | µ = 0.08 mm−1 |
β = 104.56 (1)° | T = 298 K |
V = 3089.8 (16) Å3 | Parallelepiped, colorless |
Z = 4 | 0.50 × 0.50 × 0.40 mm |
Siemens R3m diffractometer | 1461 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.089 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = 0→12 |
Absorption correction: empirical (using intensity measurements) ψ scan (North et al., 1968) | k = 0→18 |
Tmin = 0.912, Tmax = 1.000 | l = −23→23 |
2879 measured reflections | 2 standard reflections every 118 reflections |
2715 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
2715 reflections | Δρmax = 0.18 e Å−3 |
181 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (1) |
2C12H24N+·C6H8O42−·H2O | V = 3089.8 (16) Å3 |
Mr = 526.78 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 10.155 (3) Å | µ = 0.08 mm−1 |
b = 15.638 (5) Å | T = 298 K |
c = 20.102 (6) Å | 0.50 × 0.50 × 0.40 mm |
β = 104.56 (1)° |
Siemens R3m diffractometer | 1461 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) ψ scan (North et al., 1968) | Rint = 0.089 |
Tmin = 0.912, Tmax = 1.000 | 2 standard reflections every 118 reflections |
2879 measured reflections | intensity decay: none |
2715 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.18 e Å−3 |
2715 reflections | Δρmin = −0.18 e Å−3 |
181 parameters |
Refinement. Riding, U(H) = 1.5Ueq(C). The N– and O-bonded H-atoms were located and refined. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4503 (2) | 0.2493 (2) | 0.3782 (1) | 0.060 (1) | |
O2 | 0.2711 (2) | 0.2268 (2) | 0.2918 (1) | 0.066 (1) | |
O3 | 0.0000 | 0.3095 (3) | 0.2500 | 0.083 (1) | |
N1 | 0.6777 (2) | 0.2361 (2) | 0.3340 (1) | 0.033 (1) | |
C1 | 0.3262 (3) | 0.2382 (2) | 0.3538 (1) | 0.036 (1) | |
C2 | 0.2333 (2) | 0.2380 (2) | 0.4022 (1) | 0.037 (1) | |
C3 | 0.2995 (2) | 0.2516 (2) | 0.4775 (1) | 0.039 (1) | |
C4 | 0.7297 (2) | 0.1542 (2) | 0.3695 (1) | 0.034 (1) | |
C5 | 0.6401 (3) | 0.0821 (2) | 0.3342 (2) | 0.050 (1) | |
C6 | 0.6864 (3) | −0.0038 (2) | 0.3674 (2) | 0.063 (1) | |
C7 | 0.8353 (4) | −0.0201 (2) | 0.3721 (2) | 0.069 (1) | |
C8 | 0.9224 (3) | 0.0538 (2) | 0.4071 (2) | 0.071 (1) | |
C9 | 0.8772 (3) | 0.1379 (2) | 0.3709 (2) | 0.052 (1) | |
C10 | 0.7601 (2) | 0.3155 (2) | 0.3564 (1) | 0.033 (1) | |
C11 | 0.7927 (3) | 0.3307 (2) | 0.4334 (1) | 0.044 (1) | |
C12 | 0.8804 (3) | 0.4107 (2) | 0.4507 (2) | 0.051 (1) | |
C13 | 0.8098 (3) | 0.4889 (2) | 0.4126 (2) | 0.062 (1) | |
C14 | 0.7664 (3) | 0.4730 (2) | 0.3359 (2) | 0.063 (1) | |
C15 | 0.6831 (3) | 0.3913 (2) | 0.3181 (2) | 0.049 (1) | |
H1a | 0.590 (3) | 0.247 (2) | 0.343 (1) | 0.055 (8)* | |
H1b | 0.674 (3) | 0.230 (2) | 0.287 (1) | 0.040 (7)* | |
H3w | 0.069 (5) | 0.268 (3) | 0.263 (3) | 0.17 (2)* | |
H2a | 0.1651 | 0.2821 | 0.3874 | 0.055* | |
H2b | 0.1862 | 0.1835 | 0.3973 | 0.055* | |
H3a | 0.3446 | 0.3068 | 0.4832 | 0.058* | |
H3b | 0.3686 | 0.2081 | 0.4928 | 0.058* | |
H4 | 0.7218 | 0.1579 | 0.4170 | 0.051* | |
H5a | 0.6414 | 0.0805 | 0.2861 | 0.075* | |
H5b | 0.5472 | 0.0926 | 0.3364 | 0.075* | |
H6a | 0.6326 | −0.0488 | 0.3403 | 0.094* | |
H6b | 0.6710 | −0.0056 | 0.4130 | 0.094* | |
H7a | 0.8634 | −0.0722 | 0.3979 | 0.103* | |
H7b | 0.8484 | −0.0279 | 0.3263 | 0.103* | |
H8a | 0.9170 | 0.0575 | 0.4545 | 0.106* | |
H8b | 1.0166 | 0.0430 | 0.4072 | 0.106* | |
H9a | 0.8880 | 0.1359 | 0.3243 | 0.079* | |
H9b | 0.9332 | 0.1840 | 0.3951 | 0.079* | |
H10 | 0.8462 | 0.3097 | 0.3432 | 0.049* | |
H11a | 0.8407 | 0.2818 | 0.4576 | 0.066* | |
H11b | 0.7091 | 0.3382 | 0.4477 | 0.066* | |
H12a | 0.9004 | 0.4209 | 0.4998 | 0.076* | |
H12b | 0.9659 | 0.4014 | 0.4386 | 0.076* | |
H13a | 0.8712 | 0.5374 | 0.4221 | 0.093* | |
H13b | 0.7303 | 0.5025 | 0.4290 | 0.093* | |
H14a | 0.7129 | 0.5212 | 0.3136 | 0.094* | |
H14b | 0.8469 | 0.4689 | 0.3184 | 0.094* | |
H15a | 0.5970 | 0.3979 | 0.3303 | 0.074* | |
H15b | 0.6639 | 0.3809 | 0.2691 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.030 (1) | 0.101 (2) | 0.057 (1) | −0.003 (1) | 0.026 (1) | −0.008 (2) |
O2 | 0.056 (1) | 0.117 (2) | 0.029 (1) | −0.004 (1) | 0.019 (1) | −0.005 (1) |
O3 | 0.056 (2) | 0.119 (4) | 0.072 (2) | 0.000 | 0.014 (2) | 0.000 |
N1 | 0.022 (1) | 0.051 (2) | 0.026 (1) | 0.000 (1) | 0.009 (1) | 0.001 (1) |
C1 | 0.036 (2) | 0.041 (2) | 0.036 (2) | 0.003 (1) | 0.017 (1) | 0.001 (1) |
C2 | 0.027 (1) | 0.055 (2) | 0.033 (1) | −0.002 (1) | 0.014 (1) | 0.002 (1) |
C3 | 0.026 (1) | 0.061 (2) | 0.030 (1) | 0.002 (1) | 0.011 (1) | 0.004 (1) |
C4 | 0.027 (1) | 0.047 (2) | 0.031 (2) | −0.001 (1) | 0.009 (1) | 0.001 (1) |
C5 | 0.036 (2) | 0.055 (2) | 0.056 (2) | −0.006 (2) | 0.008 (2) | −0.011 (2) |
C6 | 0.063 (2) | 0.047 (2) | 0.080 (2) | −0.011 (2) | 0.020 (2) | −0.007 (2) |
C7 | 0.069 (2) | 0.056 (2) | 0.083 (3) | 0.017 (2) | 0.023 (2) | 0.004 (2) |
C8 | 0.043 (2) | 0.063 (2) | 0.099 (3) | 0.012 (2) | 0.006 (2) | 0.011 (2) |
C9 | 0.026 (2) | 0.058 (2) | 0.072 (2) | 0.003 (2) | 0.010 (2) | 0.007 (2) |
C10 | 0.025 (1) | 0.046 (2) | 0.030 (1) | −0.001 (1) | 0.011 (1) | 0.003 (1) |
C11 | 0.041 (2) | 0.056 (2) | 0.035 (2) | −0.004 (2) | 0.010 (1) | −0.001 (1) |
C12 | 0.041 (2) | 0.059 (2) | 0.049 (2) | −0.011 (2) | 0.005 (2) | −0.007 (2) |
C13 | 0.046 (2) | 0.056 (2) | 0.079 (2) | −0.001 (2) | 0.006 (2) | −0.011 (2) |
C14 | 0.062 (2) | 0.048 (2) | 0.072 (2) | −0.005 (2) | 0.004 (2) | 0.014 (2) |
C15 | 0.047 (2) | 0.049 (2) | 0.047 (2) | 0.004 (2) | 0.004 (2) | 0.007 (2) |
O1—C1 | 1.244 (3) | C3—H3a | 0.9700 |
O2—C1 | 1.243 (3) | C3—H3b | 0.9700 |
N1—C4 | 1.496 (3) | C4—H4 | 0.9800 |
N1—C10 | 1.501 (3) | C5—H5a | 0.9702 |
C1—C2 | 1.515 (3) | C5—H5b | 0.9700 |
C2—C3 | 1.509 (3) | C6—H6a | 0.9700 |
C3—C3i | 1.514 (5) | C6—H6b | 0.9700 |
C4—C5 | 1.509 (4) | C7—H7a | 0.9700 |
C4—C9 | 1.513 (4) | C7—H7b | 0.9699 |
C5—C6 | 1.522 (4) | C8—H8a | 0.9701 |
C6—C7 | 1.512 (5) | C8—H8b | 0.9699 |
C7—C8 | 1.516 (4) | C9—H9a | 0.9698 |
C8—C9 | 1.518 (4) | C9—H9b | 0.9700 |
C10—C11 | 1.517 (3) | C10—H10 | 0.9800 |
C10—C15 | 1.519 (4) | C11—H11a | 0.9700 |
C11—C12 | 1.523 (4) | C11—H11b | 0.9700 |
C12—C13 | 1.524 (4) | C12—H12a | 0.9698 |
C13—C14 | 1.513 (4) | C12—H12b | 0.9701 |
C14—C15 | 1.525 (4) | C13—H13a | 0.9700 |
O3—H3w | 0.95 (4) | C13—H13b | 0.9700 |
N1—H1a | 0.97 (3) | C14—H14a | 0.9700 |
N1—H1b | 0.94 (3) | C14—H14b | 0.9701 |
C2—H2a | 0.9700 | C15—H15a | 0.9701 |
C2—H2b | 0.9700 | C15—H15b | 0.9699 |
C4—N1—C10 | 117.5 (2) | C7—C6—H6b | 109.5 |
O2—C1—O1 | 124.8 (2) | C5—C6—H6b | 109.6 |
O2—C1—C2 | 116.5 (2) | H6a—C6—H6b | 107.9 |
O1—C1—C2 | 118.6 (2) | C6—C7—H7a | 109.3 |
C3—C2—C1 | 116.8 (2) | C8—C7—H7a | 109.4 |
C2—C3—C3i | 113.6 (3) | C6—C7—H7b | 109.6 |
N1—C4—C5 | 108.5 (2) | C8—C7—H7b | 109.5 |
N1—C4—C9 | 112.5 (2) | H7a—C7—H7b | 108.0 |
C5—C4—C9 | 111.1 (2) | C7—C8—H8a | 109.4 |
C4—C5—C6 | 111.7 (2) | C9—C8—H8a | 109.5 |
C7—C6—C5 | 111.7 (3) | C7—C8—H8b | 109.2 |
C6—C7—C8 | 111.0 (3) | C9—C8—H8b | 109.3 |
C7—C8—C9 | 111.5 (3) | H8a—C8—H8b | 107.9 |
C4—C9—C8 | 109.5 (2) | C4—C9—H9a | 109.8 |
N1—C10—C11 | 113.5 (2) | C8—C9—H9a | 110.0 |
N1—C10—C15 | 108.4 (2) | C4—C9—H9b | 109.7 |
C11—C10—C15 | 110.3 (2) | C8—C9—H9b | 109.6 |
C10—C11—C12 | 109.2 (2) | H9a—C9—H9b | 108.2 |
C11—C12—C13 | 111.7 (2) | N1—C10—H10 | 108.1 |
C14—C13—C12 | 111.1 (3) | C11—C10—H10 | 108.1 |
C13—C14—C15 | 112.3 (3) | C15—C10—H10 | 108.3 |
C10—C15—C14 | 110.5 (2) | C10—C11—H11a | 109.9 |
C4—N1—H1a | 108 (2) | C12—C11—H11a | 110.0 |
C10—N1—H1a | 106 (2) | C10—C11—H11b | 109.8 |
C4—N1—H1b | 108 (2) | C12—C11—H11b | 109.7 |
C10—N1—H1b | 105 (2) | H11a—C11—H11b | 108.3 |
H1a—N1—H1b | 113 (2) | C11—C12—H12a | 109.2 |
C3—C2—H2a | 108.1 | C13—C12—H12a | 109.4 |
C1—C2—H2a | 108.3 | C11—C12—H12b | 109.2 |
C3—C2—H2b | 108.0 | C13—C12—H12b | 109.3 |
C1—C2—H2b | 108.0 | H12a—C12—H12b | 108.0 |
H2a—C2—H2b | 107.3 | C14—C13—H13a | 109.7 |
C2—C3—H3a | 108.8 | C12—C13—H13a | 109.4 |
C3i—C3—H3a | 108.9 | C14—C13—H13b | 109.2 |
C2—C3—H3b | 108.8 | C12—C13—H13b | 109.4 |
C3i—C3—H3b | 108.9 | H13a—C13—H13b | 108.0 |
H3a—C3—H3b | 107.7 | C13—C14—H14a | 109.2 |
N1—C4—H4 | 108.0 | C15—C14—H14a | 109.2 |
C5—C4—H4 | 108.4 | C13—C14—H14b | 109.0 |
C9—C4—H4 | 108.3 | C15—C14—H14b | 109.2 |
C4—C5—H5a | 109.3 | H14a—C14—H14b | 107.9 |
C6—C5—H5a | 109.5 | C10—C15—H15a | 109.7 |
C4—C5—H5b | 109.3 | C14—C15—H15a | 109.5 |
C6—C5—H5b | 109.1 | C10—C15—H15b | 109.3 |
H5a—C5—H5b | 107.9 | C14—C15—H15b | 109.7 |
C7—C6—H6a | 109.1 | H15a—C15—H15b | 108.1 |
C5—C6—H6a | 109.0 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1a···O1 | 0.97 (3) | 1.74 (3) | 2.683 (3) | 165 (2) |
N1—H1b···O2ii | 0.94 (2) | 1.81 (2) | 2.711 (3) | 160 (3) |
O3—H3w···O2 | 0.94 (5) | 2.09 (5) | 2.966 (3) | 154 (4) |
Symmetry code: (ii) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | 2C12H24N+·C6H8O42−·H2O |
Mr | 526.78 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.155 (3), 15.638 (5), 20.102 (6) |
β (°) | 104.56 (1) |
V (Å3) | 3089.8 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Siemens R3m diffractometer |
Absorption correction | Empirical (using intensity measurements) ψ scan (North et al., 1968) |
Tmin, Tmax | 0.912, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2879, 2715, 1461 |
Rint | 0.089 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.159, 0.98 |
No. of reflections | 2715 |
No. of parameters | 181 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: XSCANS (Siemens, 1990), XSCANS, SHELXTL-Plus (Sheldrick, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97.
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Dicyclohexylammonium monoalkanoates, [(cyclo-C6H11)2NH2] RCH2CO2] (R is an electron-withdrawing group), typically exist as dimeric ion pairs in which the two NH2 units link two CO2 units to form an eight-membered N···O≐C≐O···N···O≐C≐O··· ring, or as linear hydrogen-bonded chains (Ng et al., 1999). The ring architecture probably requires sterically bulky R groups; the R = (CH3)2NCS2 derivative adopts the ring architecture, but the compound has water molecules that link adjacent dimers [Owater···Ocarboxyl 2.784 (6) and 3.029 (7) Å; Ng, 1992]. In the title compound, both carboxyl ends of the centrosymmetric adipate dianion are engaged in a similar type of ring formation to give rise to a chain and adjacent chains are linked through the lattice water molecule [Owater···O 2.966 (3) Å] to form layers. The water molecule lies on a twofold axis.
A layer structure is also adopted by m-xylyleammonium adipate, which crystallizes as a monohydrate, but its N···Ocarboxyl hydrogen bonds in the chains are somewhat longer. The chains are links into layers through the lattice water molecules (Moritani & Kashino, 1991). A chain structure is also adopted by anhydrous piperazinium adipate, which displays hydrogen bonds (Vanier & Brisse, 1983) that are somewhat longer than those in the dicyclohexylammonium salt. Slightly longer hydrogen bonds are also noted in hexamethylediammonium adipate (Brown, 1966).