

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100019326/sk1439sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270100019326/sk1439Isup2.hkl |
CCDC reference: 162569
The compound was the unexpected product from the attempted condensation of dicyclohexylammonium hydrogen 3-thienylmalonate and dibutyltin oxide in ethanol. The ammonium hydrogen carboxylate was prepared by treating equimolar quantities of dicyclohexylamine and 3-thienylmalonic acid in ethanol; the reagent was heated with dibutyltin oxide (2/1 molar ratio) until the oxide dissolved completely. The title compound separated as crystals when the solution was cooled.
All hydrogen atoms, excepting the hydrogen atoms attached to the disordered portion of the molecule, are located from difference maps and isotropically refined. Those attached to the disordered portion (H5 and H5') are geometrically fixed and allowed to ride on the parent atoms with Uiso = 1.2Ueq.
The sulfur at the 3-position of the thiophene ring is disordered with respect to the carbon atom at the 4-position. The occupancy refined to almost 3:1, and this was then fixed as 3:1. Carbon-sulfur distances were restrained to be equal by an SADI 0.01 instruction in SHELXTL. The temperature factor of S1 was set to be equal to that of C5', and that of S1' to that of C5.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
![]() | Fig. 1. ORTEPII (Johnson, 1976) diagram of the dimeric title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
2C12H24N·2C6H5O2S | Z = 1 |
Mr = 646.96 | F(000) = 352 |
Triclinic, P1 | Dx = 1.158 Mg m−3 |
a = 8.8444 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7581 (2) Å | Cell parameters from 4250 reflections |
c = 11.9220 (3) Å | θ = 1.9–28.2° |
α = 112.009 (1)° | µ = 0.18 mm−1 |
β = 94.990 (1)° | T = 298 K |
γ = 99.585 (1)° | Block, colorless |
V = 927.98 (4) Å3 | 0.48 × 0.44 × 0.34 mm |
Siemens SMART CCD area detector diffractometer | 4299 independent reflections |
Radiation source: fine-focus sealed tube | 2833 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.2°, θmin = 1.9° |
ω scan | h = −11→11 |
Absorption correction: empirical SADABS (Sheldrick, 1996) | k = −12→12 |
Tmin = 0.918, Tmax = 0.941 | l = −15→7 |
6549 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0865P)2] where P = (Fo2 + 2Fc2)/3 |
4299 reflections | (Δ/σ)max = 0.001 |
317 parameters | Δρmax = 0.25 e Å−3 |
6 restraints | Δρmin = −0.33 e Å−3 |
2C12H24N·2C6H5O2S | γ = 99.585 (1)° |
Mr = 646.96 | V = 927.98 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.8444 (3) Å | Mo Kα radiation |
b = 9.7581 (2) Å | µ = 0.18 mm−1 |
c = 11.9220 (3) Å | T = 298 K |
α = 112.009 (1)° | 0.48 × 0.44 × 0.34 mm |
β = 94.990 (1)° |
Siemens SMART CCD area detector diffractometer | 4299 independent reflections |
Absorption correction: empirical SADABS (Sheldrick, 1996) | 2833 reflections with I > 2σ(I) |
Tmin = 0.918, Tmax = 0.941 | Rint = 0.047 |
6549 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 6 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.25 e Å−3 |
4299 reflections | Δρmin = −0.33 e Å−3 |
317 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analyzing the duplicate reflections, and was found to be negligible. The structure was solved by direct methods and refined by full-matrix least-squares techniques. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.3478 (1) | −0.2480 (1) | 0.1187 (1) | 0.068 (1) | 0.75 |
S1' | 0.451 (1) | −0.1818 (9) | 0.0375 (5) | 0.071 (1) | 0.25 |
O1 | 0.7118 (2) | 0.3175 (2) | 0.3948 (1) | 0.065 (1) | |
O2 | 0.5385 (2) | 0.2468 (2) | 0.4979 (1) | 0.056 (1) | |
N1 | 0.7148 (2) | 0.6196 (2) | 0.4819 (1) | 0.039 (1) | |
C1 | 0.6397 (2) | 0.2240 (2) | 0.4303 (2) | 0.041 (1) | |
C2 | 0.6764 (2) | 0.0652 (2) | 0.3851 (2) | 0.050 (1) | |
C3 | 0.5700 (2) | −0.0397 (2) | 0.2688 (2) | 0.041 (1) | |
C4 | 0.4430 (2) | −0.1461 (2) | 0.2632 (2) | 0.053 (1) | |
C5 | 0.474 (1) | −0.148 (1) | 0.0621 (8) | 0.071 (1) | 0.75 |
C5' | 0.370 (2) | −0.224 (2) | 0.149 (1) | 0.068 (1) | 0.25 |
C6 | 0.5868 (2) | −0.0438 (2) | 0.1515 (2) | 0.056 (1) | |
C7 | 0.8026 (2) | 0.6889 (2) | 0.6111 (2) | 0.042 (1) | |
C8 | 0.7032 (2) | 0.6303 (2) | 0.6897 (2) | 0.053 (1) | |
C9 | 0.7817 (3) | 0.6986 (3) | 0.8239 (2) | 0.066 (1) | |
C10 | 0.8176 (3) | 0.8704 (3) | 0.8740 (2) | 0.070 (1) | |
C11 | 0.9169 (3) | 0.9282 (3) | 0.7964 (2) | 0.068 (1) | |
C12 | 0.8399 (2) | 0.8618 (2) | 0.6620 (2) | 0.051 (1) | |
C13 | 0.7879 (2) | 0.6623 (2) | 0.3868 (2) | 0.040 (1) | |
C14 | 0.9486 (2) | 0.6249 (2) | 0.3770 (2) | 0.051 (1) | |
C15 | 1.0190 (3) | 0.6659 (3) | 0.2780 (2) | 0.065 (1) | |
C16 | 0.9121 (3) | 0.5903 (3) | 0.1555 (2) | 0.067 (1) | |
C17 | 0.7492 (3) | 0.6226 (3) | 0.1653 (2) | 0.063 (1) | |
C18 | 0.6804 (2) | 0.5803 (2) | 0.2636 (2) | 0.050 (1) | |
H1a | 0.701 (3) | 0.507 (3) | 0.457 (2) | 0.09 (1)* | |
H1b | 0.625 (2) | 0.656 (2) | 0.493 (2) | 0.06 (1)* | |
H2a | 0.663 (3) | 0.022 (3) | 0.451 (2) | 0.07 (1)* | |
H2b | 0.779 (3) | 0.070 (3) | 0.365 (2) | 0.08 (1)* | |
H4 | 0.416 (3) | −0.164 (3) | 0.332 (2) | 0.07 (1)* | |
H5 | 0.4658 | −0.1628 | −0.0201 | 0.085* | 0.75 |
H5' | 0.2797 | −0.2972 | 0.1306 | 0.082* | 0.25 |
H6 | 0.668 (3) | 0.022 (3) | 0.135 (2) | 0.09 (1)* | |
H7 | 0.898 (2) | 0.647 (2) | 0.604 (2) | 0.05 (1)* | |
H8a | 0.690 (3) | 0.523 (3) | 0.654 (2) | 0.07 (1)* | |
H8b | 0.600 (3) | 0.659 (3) | 0.678 (2) | 0.08 (1)* | |
H9a | 0.714 (3) | 0.661 (3) | 0.870 (2) | 0.08 (1)* | |
H9b | 0.878 (3) | 0.668 (3) | 0.831 (2) | 0.08 (1)* | |
H10a | 0.869 (3) | 0.920 (3) | 0.965 (3) | 0.09 (1)* | |
H10b | 0.714 (3) | 0.908 (3) | 0.875 (2) | 0.10 (1)* | |
H11a | 0.938 (3) | 1.041 (4) | 0.833 (3) | 0.11 (1)* | |
H11b | 1.019 (3) | 0.896 (3) | 0.802 (2) | 0.08 (1)* | |
H12a | 0.908 (3) | 0.900 (2) | 0.616 (2) | 0.07 (1)* | |
H12b | 0.743 (2) | 0.897 (2) | 0.656 (2) | 0.06 (1)* | |
H13 | 0.792 (2) | 0.772 (2) | 0.409 (2) | 0.05 (1)* | |
H14a | 1.018 (3) | 0.678 (3) | 0.458 (2) | 0.07 (1)* | |
H14b | 0.938 (2) | 0.518 (3) | 0.359 (2) | 0.06 (1)* | |
H15a | 1.125 (3) | 0.634 (3) | 0.269 (2) | 0.08 (1)* | |
H15b | 1.031 (3) | 0.772 (3) | 0.298 (2) | 0.08 (1)* | |
H16a | 0.950 (3) | 0.621 (3) | 0.094 (2) | 0.08 (1)* | |
H16b | 0.898 (3) | 0.471 (3) | 0.120 (2) | 0.08 (1)* | |
H17a | 0.685 (3) | 0.568 (3) | 0.085 (2) | 0.08 (1)* | |
H17b | 0.754 (3) | 0.726 (3) | 0.186 (2) | 0.08 (1)* | |
H18a | 0.582 (2) | 0.606 (2) | 0.273 (2) | 0.06 (1)* | |
H18b | 0.669 (3) | 0.470 (3) | 0.244 (2) | 0.08 (1)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.073 (1) | 0.053 (1) | 0.058 (1) | −0.002 (1) | 0.003 (1) | 0.007 (1) |
S1' | 0.094 (2) | 0.072 (3) | 0.048 (2) | 0.023 (2) | 0.018 (2) | 0.023 (2) |
O1 | 0.083 (1) | 0.042 (1) | 0.074 (1) | 0.012 (1) | 0.028 (1) | 0.024 (1) |
O2 | 0.060 (1) | 0.061 (1) | 0.056 (1) | 0.030 (1) | 0.020 (1) | 0.024 (1) |
N1 | 0.042 (1) | 0.038 (1) | 0.036 (1) | 0.011 (1) | 0.007 (1) | 0.012 (1) |
C1 | 0.046 (1) | 0.036 (1) | 0.037 (1) | 0.012 (1) | 0.001 (1) | 0.010 (1) |
C2 | 0.053 (1) | 0.042 (1) | 0.056 (1) | 0.020 (1) | 0.008 (1) | 0.017 (1) |
C3 | 0.050 (1) | 0.034 (1) | 0.047 (1) | 0.018 (1) | 0.018 (1) | 0.018 (1) |
C4 | 0.068 (1) | 0.042 (1) | 0.050 (1) | 0.007 (1) | 0.022 (1) | 0.018 (1) |
C5 | 0.094 (2) | 0.072 (3) | 0.048 (2) | 0.023 (2) | 0.018 (2) | 0.023 (2) |
C5' | 0.073 (1) | 0.053 (1) | 0.058 (1) | −0.002 (1) | 0.003 (1) | 0.007 (1) |
C6 | 0.063 (1) | 0.059 (1) | 0.054 (1) | 0.015 (1) | 0.019 (1) | 0.031 (1) |
C7 | 0.043 (1) | 0.044 (1) | 0.035 (1) | 0.012 (1) | 0.005 (1) | 0.011 (1) |
C8 | 0.065 (1) | 0.049 (1) | 0.042 (1) | 0.007 (1) | 0.007 (1) | 0.018 (1) |
C9 | 0.077 (2) | 0.079 (2) | 0.043 (1) | 0.017 (1) | 0.008 (1) | 0.026 (1) |
C10 | 0.071 (1) | 0.078 (2) | 0.038 (1) | 0.007 (1) | 0.005 (1) | 0.004 (1) |
C11 | 0.063 (1) | 0.068 (1) | 0.048 (1) | −0.005 (1) | −0.002 (1) | 0.005 (1) |
C12 | 0.052 (1) | 0.044 (1) | 0.046 (1) | 0.002 (1) | 0.005 (1) | 0.010 (1) |
C13 | 0.049 (1) | 0.035 (1) | 0.039 (1) | 0.012 (1) | 0.012 (1) | 0.014 (1) |
C14 | 0.043 (1) | 0.059 (1) | 0.051 (1) | 0.011 (1) | 0.010 (1) | 0.021 (1) |
C15 | 0.059 (1) | 0.070 (1) | 0.069 (2) | 0.012 (1) | 0.028 (1) | 0.027 (1) |
C16 | 0.082 (2) | 0.075 (2) | 0.055 (1) | 0.029 (1) | 0.034 (1) | 0.027 (1) |
C17 | 0.084 (2) | 0.073 (2) | 0.044 (1) | 0.037 (1) | 0.021 (1) | 0.026 (1) |
C18 | 0.049 (1) | 0.059 (1) | 0.042 (1) | 0.021 (1) | 0.009 (1) | 0.018 (1) |
S1—C4 | 1.689 (2) | C2—H2a | 1.02 (2) |
S1—C5 | 1.708 (8) | C2—H2b | 0.96 (3) |
S1'—C6 | 1.704 (6) | C4—H4 | 0.94 (2) |
S1'—C5' | 1.711 (8) | C5—H5 | 0.9300 |
O1—C1 | 1.249 (2) | C5'—H5' | 0.9300 |
O2—C1 | 1.248 (2) | C6—H6 | 0.97 (3) |
N1—C7 | 1.506 (2) | C7—H7 | 0.99 (2) |
N1—C13 | 1.507 (2) | C8—H8a | 0.95 (3) |
C1—C2 | 1.539 (2) | C8—H8b | 1.01 (2) |
C2—C3 | 1.498 (3) | C9—H9a | 0.97 (2) |
C3—C4 | 1.375 (2) | C9—H9b | 0.95 (3) |
C3—C6 | 1.405 (3) | C10—H10a | 1.03 (3) |
C4—C5' | 1.32 (1) | C10—H10b | 1.04 (3) |
C5—C6 | 1.352 (9) | C11—H11a | 1.00 (3) |
C7—C12 | 1.528 (2) | C11—H11b | 1.01 (2) |
C7—C8 | 1.535 (2) | C12—H12a | 0.97 (2) |
C8—C9 | 1.530 (3) | C12—H12b | 0.98 (2) |
C9—C10 | 1.519 (3) | C13—H13 | 0.99 (2) |
C10—C11 | 1.521 (3) | C14—H14a | 0.99 (2) |
C11—C12 | 1.528 (3) | C14—H14b | 0.97 (2) |
C13—C18 | 1.525 (2) | C15—H15a | 1.04 (2) |
C13—C14 | 1.528 (2) | C15—H15b | 0.95 (3) |
C14—C15 | 1.529 (3) | C16—H16a | 0.95 (3) |
C15—C16 | 1.514 (3) | C16—H16b | 1.06 (2) |
C16—C17 | 1.530 (3) | C17—H17a | 0.97 (2) |
C17—C18 | 1.522 (3) | C17—H17b | 0.94 (3) |
N1—H1a | 1.00 (3) | C18—H18a | 0.95 (2) |
N1—H1b | 0.92 (2) | C18—H18b | 0.99 (3) |
C4—S1—C5 | 91.4 (3) | C8—C7—H7 | 110 (1) |
C6—S1'—C5' | 87.5 (6) | C9—C8—H8a | 113 (1) |
C7—N1—C13 | 117.6 (1) | C7—C8—H8a | 105 (1) |
O2—C1—O1 | 125.9 (2) | C9—C8—H8b | 113 (1) |
O2—C1—C2 | 116.7 (2) | C7—C8—H8b | 105 (1) |
O1—C1—C2 | 117.4 (2) | H8a—C8—H8b | 110 (2) |
C3—C2—C1 | 110.9 (1) | C10—C9—H9a | 111 (2) |
C4—C3—C6 | 111.1 (2) | C8—C9—H9a | 108 (1) |
C4—C3—C2 | 124.0 (2) | C10—C9—H9b | 108 (2) |
C6—C3—C2 | 125.0 (2) | C8—C9—H9b | 110 (1) |
C5'—C4—C3 | 111.3 (6) | H9a—C9—H9b | 109 (2) |
C3—C4—S1 | 112.6 (2) | C9—C10—H10a | 113 (2) |
C6—C5—S1 | 111.8 (5) | C11—C10—H10a | 111 (2) |
C4—C5'—S1' | 116.6 (9) | C9—C10—H10b | 109 (2) |
C5—C6—C3 | 113.1 (4) | C11—C10—H10b | 110 (2) |
C3—C6—S1' | 113.3 (3) | H10a—C10—H10b | 103 (2) |
N1—C7—C12 | 112.1 (1) | C10—C11—H11a | 109 (2) |
N1—C7—C8 | 107.5 (1) | C12—C11—H11a | 112 (2) |
C12—C7—C8 | 111.3 (2) | C10—C11—H11b | 108 (1) |
C9—C8—C7 | 111.1 (2) | C12—C11—H11b | 109 (1) |
C10—C9—C8 | 110.9 (2) | H11a—C11—H11b | 108 (2) |
C9—C10—C11 | 111.1 (2) | C11—C12—H12a | 109 (1) |
C10—C11—C12 | 111.7 (2) | C7—C12—H12a | 112 (1) |
C11—C12—C7 | 110.6 (2) | C11—C12—H12b | 109 (1) |
N1—C13—C18 | 109.0 (1) | C7—C12—H12b | 109 (1) |
N1—C13—C14 | 111.7 (1) | H12a—C12—H12b | 108 (2) |
C18—C13—C14 | 110.6 (1) | N1—C13—H13 | 108 (1) |
C13—C14—C15 | 110.8 (2) | C18—C13—H13 | 106 (1) |
C16—C15—C14 | 111.6 (2) | C14—C13—H13 | 112 (1) |
C15—C16—C17 | 111.9 (2) | C13—C14—H14a | 110 (1) |
C18—C17—C16 | 111.4 (2) | C15—C14—H14a | 111 (1) |
C17—C18—C13 | 110.6 (2) | C13—C14—H14b | 108 (1) |
C7—N1—H1a | 105 (2) | C15—C14—H14b | 111 (1) |
C13—N1—H1a | 109 (1) | H14a—C14—H14b | 106 (2) |
C7—N1—H1b | 102 (1) | C16—C15—H15a | 110 (1) |
C13—N1—H1b | 109 (1) | C14—C15—H15a | 110 (1) |
H1a—N1—H1b | 115 (2) | C16—C15—H15b | 105 (1) |
C3—C2—H2a | 109 (1) | C14—C15—H15b | 110 (1) |
C1—C2—H2a | 110 (1) | H15a—C15—H15b | 111 (2) |
C3—C2—H2b | 105 (1) | C15—C16—H16a | 113 (2) |
C1—C2—H2b | 110 (2) | C17—C16—H16a | 108 (1) |
H2a—C2—H2b | 112 (2) | C15—C16—H16b | 112 (1) |
C5'—C4—H4 | 125 (2) | C17—C16—H16b | 106 (1) |
C3—C4—H4 | 124 (1) | H16a—C16—H16b | 106 (2) |
S1—C4—H4 | 124 (1) | C18—C17—H17a | 112 (1) |
C6—C5—H5 | 124.1 | C16—C17—H17a | 108 (1) |
S1—C5—H5 | 124.1 | C18—C17—H17b | 108 (1) |
C4—C5'—H5' | 121.7 | C16—C17—H17b | 110 (2) |
S1'—C5'—H5' | 121.7 | H17a—C17—H17b | 108 (2) |
C5—C6—H6 | 123 (2) | C17—C18—H18a | 112 (1) |
C3—C6—H6 | 124 (1) | C13—C18—H18a | 108 (1) |
S1'—C6—H6 | 122 (1) | C17—C18—H18b | 111 (1) |
N1—C7—H7 | 104 (1) | C13—C18—H18b | 106 (1) |
C12—C7—H7 | 112 (1) | H18a—C18—H18b | 109 (2) |
O2—C1—C2—C3 | 87.8 (2) | C13—N1—C7—C8 | 179.0 (1) |
O1—C1—C2—C3 | −91.3 (2) | N1—C7—C8—C9 | −178.4 (2) |
C1—C2—C3—C4 | −101.4 (2) | C12—C7—C8—C9 | −55.4 (2) |
C1—C2—C3—C6 | 79.1 (2) | C7—C8—C9—C10 | 55.7 (2) |
C6—C3—C4—C5' | 0 (1) | C8—C9—C10—C11 | −56.1 (3) |
C2—C3—C4—C5' | −180 (1) | C9—C10—C11—C12 | 56.4 (3) |
C6—C3—C4—S1 | 0.2 (2) | C10—C11—C12—C7 | −55.6 (3) |
C2—C3—C4—S1 | −179.4 (1) | N1—C7—C12—C11 | 175.4 (2) |
C5—S1—C4—C3 | −1.2 (5) | C8—C7—C12—C11 | 55.0 (2) |
C4—S1—C5—C6 | 1.9 (9) | C7—N1—C13—C18 | −179.9 (1) |
C3—C4—C5'—S1' | 3 (2) | C7—N1—C13—C14 | 57.6 (2) |
C6—S1'—C5'—C4 | −3 (2) | N1—C13—C14—C15 | 178.8 (2) |
S1—C5—C6—C3 | −2 (1) | C18—C13—C14—C15 | 57.2 (2) |
C4—C3—C6—C5 | 1.3 (7) | C13—C14—C15—C16 | −55.1 (3) |
C2—C3—C6—C5 | −179.2 (7) | C14—C15—C16—C17 | 53.5 (3) |
C4—C3—C6—S1' | −2.3 (4) | C15—C16—C17—C18 | −54.1 (3) |
C2—C3—C6—S1' | 177.3 (4) | C16—C17—C18—C13 | 56.0 (2) |
C5'—S1'—C6—C3 | 3.0 (9) | N1—C13—C18—C17 | 179.1 (1) |
C13—N1—C7—C12 | 56.5 (2) | C14—C13—C18—C17 | −57.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1a···O1 | 1.01 (3) | 1.74 (3) | 2.728 (3) | 167 (2) |
N1—H1b···O2i | 0.92 (2) | 1.85 (2) | 2.758 (3) | 169 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | 2C12H24N·2C6H5O2S |
Mr | 646.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.8444 (3), 9.7581 (2), 11.9220 (3) |
α, β, γ (°) | 112.009 (1), 94.990 (1), 99.585 (1) |
V (Å3) | 927.98 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.48 × 0.44 × 0.34 |
Data collection | |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Empirical SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.918, 0.941 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6549, 4299, 2833 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.162, 0.93 |
No. of reflections | 4299 |
No. of parameters | 317 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.33 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
S1—C4 | 1.689 (2) | O2—C1 | 1.248 (2) |
S1—C5 | 1.708 (8) | N1—C7 | 1.506 (2) |
O1—C1 | 1.249 (2) | N1—C13 | 1.507 (2) |
C7—N1—C13 | 117.6 (1) | O2—C1—O1 | 125.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1a···O1 | 1.01 (3) | 1.74 (3) | 2.728 (3) | 167 (2) |
N1—H1b···O2i | 0.92 (2) | 1.85 (2) | 2.758 (3) | 169 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
The dicyclohexylammonium salts of a number of substituted acetic acids have been structurally documented; the acids include, for example, 2,4-dichlorophenoxyacetic (Subramanian et al., 2000), various dithiocarbamylacetic acids (Ng & Hook, 1999) and trifluoroacetic acid (Ng et al., 1999). With the exceptions of the trifluoroacetate, which adopts a zigzag hydrogen-bonded chain structure and the N,N-dimethyldithocarbamylacetate, which crystallizes as a monohydrate (Ng, 1992), the dicyclohexylammonium carboxylates exists as two ion-pairs that are linked by N···O hydrogen bonds across a centre of inversion; the interactions give rise to the formation of an H—N—H···O—C—O···H—N—H···O—C—O··· ring. The short hydrogen bonds in the title compound [N···O = 2.728 (2), 2.758 (2) Å] are representative of the hydrogen bonds found in other dimeric dicyclohexylammonium carboxylates. \sch
A displacement ellipsoid plot with the numbering scheme of the dimeric title compound is shown in Fig. 1.