Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102017080/de1191sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102017080/de1191Isup2.hkl |
CCDC reference: 199440
The title compound was prepared by mixing 1,1-dimethyl-2,6-diphenyl-4,4-dimethoxycyclohexane dicarboxylate (0.01 mol), urea (0.01 mol) and methanol (10 ml), and then adding 10% of sodium methoxide (5 ml). The mixture was refluxed for 12 h, then cooled and poured onto crushed ice containing concentrated hydrochloric acid. The product thus separated was filtered and purified. Recrystallization was carried out in an ethyl acetate-hexane (2:3) mixture.
It was not possible to locate the H atoms of water molecule. Other H atoms were treated as riding, with C—H distances in the range 0.93–0.98 Å and an N—H distance of 0.86 Å. Is this added text OK?
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and ORTEP92 (Vicković, 1994); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).
C23H24N2O5·H2O | F(000) = 904 |
Mr = 426.46 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.559 (2) Å | Cell parameters from 5812 reflections |
b = 10.755 (2) Å | θ = 2.4–27.5° |
c = 15.346 (4) Å | µ = 0.09 mm−1 |
β = 114.10 (1)° | T = 293 K |
V = 2193.5 (8) Å3 | Rectangular, colourless |
Z = 4 | 0.60 × 0.55 × 0.50 mm |
Siemens SMART CCD area-detector diffractometer | 1053 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.096 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
ω scans | h = −1→15 |
5812 measured reflections | k = −1→13 |
4726 independent reflections | l = −19→18 |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 0.74 | w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3 |
4726 reflections | (Δ/σ)max = 0.024 |
282 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C23H24N2O5·H2O | V = 2193.5 (8) Å3 |
Mr = 426.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.559 (2) Å | µ = 0.09 mm−1 |
b = 10.755 (2) Å | T = 293 K |
c = 15.346 (4) Å | 0.60 × 0.55 × 0.50 mm |
β = 114.10 (1)° |
Siemens SMART CCD area-detector diffractometer | 1053 reflections with I > 2σ(I) |
5812 measured reflections | Rint = 0.096 |
4726 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 0.74 | Δρmax = 0.34 e Å−3 |
4726 reflections | Δρmin = −0.20 e Å−3 |
282 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 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating 30 initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2461 (4) | 0.1976 (5) | 0.0647 (3) | 0.0422 (13) | |
C2 | 0.2954 (4) | 0.0656 (5) | 0.0961 (3) | 0.0559 (16) | |
H2 | 0.2532 | 0.0231 | 0.1228 | 0.067* | |
C3 | 0.3967 (5) | 0.0687 (5) | 0.1740 (4) | 0.075 (2) | |
H3A | 0.4424 | 0.1063 | 0.1501 | 0.090* | |
H3B | 0.4189 | −0.0162 | 0.1920 | 0.090* | |
C4 | 0.4046 (5) | 0.1380 (5) | 0.2613 (4) | 0.0519 (16) | |
C5 | 0.3584 (4) | 0.2691 (5) | 0.2368 (4) | 0.0658 (17) | |
H5A | 0.3546 | 0.3047 | 0.2933 | 0.079* | |
H5B | 0.4028 | 0.3211 | 0.2195 | 0.079* | |
C6 | 0.2573 (4) | 0.2712 (5) | 0.1583 (3) | 0.0507 (15) | |
H6 | 0.2146 | 0.2258 | 0.1831 | 0.061* | |
C7 | 0.2111 (5) | 0.4011 (5) | 0.1355 (3) | 0.0452 (15) | |
C8 | 0.2609 (5) | 0.4980 (6) | 0.1151 (4) | 0.0629 (17) | |
H8 | 0.3252 | 0.4860 | 0.1176 | 0.076* | |
C9 | 0.2139 (5) | 0.6158 (6) | 0.0902 (4) | 0.0722 (19) | |
H9 | 0.2468 | 0.6807 | 0.0748 | 0.087* | |
C10 | 0.1220 (5) | 0.6339 (6) | 0.0886 (4) | 0.078 (2) | |
H10 | 0.0917 | 0.7116 | 0.0728 | 0.094* | |
C11 | 0.0729 (5) | 0.5380 (6) | 0.1103 (4) | 0.074 (2) | |
H11 | 0.0094 | 0.5506 | 0.1096 | 0.089* | |
C12 | 0.1171 (5) | 0.4248 (5) | 0.1328 (4) | 0.0623 (17) | |
H12 | 0.0826 | 0.3606 | 0.1469 | 0.075* | |
C13 | 0.2850 (5) | −0.0106 (5) | 0.0088 (4) | 0.0577 (16) | |
C14 | 0.2035 (5) | −0.0854 (6) | −0.0347 (4) | 0.0722 (19) | |
H14 | 0.1550 | −0.0905 | −0.0100 | 0.087* | |
C15 | 0.1912 (6) | −0.1555 (6) | −0.1169 (5) | 0.101 (3) | |
H15 | 0.1367 | −0.2092 | −0.1437 | 0.121* | |
C16 | 0.2591 (8) | −0.1444 (8) | −0.1568 (5) | 0.111 (4) | |
H16 | 0.2497 | −0.1873 | −0.2124 | 0.133* | |
C17 | 0.3403 (7) | −0.0701 (7) | −0.1143 (5) | 0.097 (3) | |
H17 | 0.3882 | −0.0646 | −0.1397 | 0.116* | |
C18 | 0.3530 (5) | −0.0023 (6) | −0.0334 (4) | 0.077 (2) | |
H18 | 0.4084 | 0.0500 | −0.0067 | 0.092* | |
C19 | 0.1364 (5) | 0.1753 (5) | 0.0061 (4) | 0.0464 (15) | |
N20 | 0.0957 (3) | 0.2099 (4) | −0.0881 (3) | 0.0492 (12) | |
H20 | 0.0347 | 0.1872 | −0.1216 | 0.059* | |
C21 | 0.1432 (4) | 0.2781 (5) | −0.1351 (4) | 0.0496 (15) | |
N22 | 0.2407 (3) | 0.3016 (4) | −0.0819 (3) | 0.0498 (12) | |
H22 | 0.2709 | 0.3438 | −0.1099 | 0.060* | |
C23 | 0.2996 (5) | 0.2683 (5) | 0.0111 (3) | 0.0509 (15) | |
O24 | 0.0823 (3) | 0.1243 (3) | 0.0394 (2) | 0.0618 (11) | |
O25 | 0.0972 (3) | 0.3105 (4) | −0.2169 (2) | 0.0706 (12) | |
O26 | 0.3874 (3) | 0.2950 (4) | 0.0469 (3) | 0.0700 (12) | |
O27 | 0.3437 (3) | 0.0797 (3) | 0.3066 (2) | 0.0606 (11) | |
C28 | 0.3688 (6) | −0.0474 (6) | 0.3371 (5) | 0.099 (2) | |
H28A | 0.3477 | −0.1008 | 0.2822 | 0.149* | |
H28B | 0.3352 | −0.0714 | 0.3769 | 0.149* | |
H28C | 0.4403 | −0.0547 | 0.3725 | 0.149* | |
O29 | 0.5036 (3) | 0.1398 (4) | 0.3236 (3) | 0.0775 (13) | |
C30 | 0.5313 (5) | 0.2085 (6) | 0.4103 (4) | 0.094 (2) | |
H30A | 0.5264 | 0.2959 | 0.3965 | 0.140* | |
H30B | 0.5993 | 0.1884 | 0.4525 | 0.140* | |
H30C | 0.4870 | 0.1873 | 0.4402 | 0.140* | |
OW | 0.0806 (3) | 0.9447 (3) | 0.1808 (2) | 0.0784 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.054 (4) | 0.030 (3) | 0.040 (3) | 0.008 (3) | 0.016 (3) | 0.006 (3) |
C2 | 0.072 (4) | 0.034 (3) | 0.054 (3) | 0.013 (3) | 0.019 (3) | 0.000 (3) |
C3 | 0.093 (5) | 0.057 (4) | 0.065 (4) | 0.033 (4) | 0.022 (4) | 0.000 (3) |
C4 | 0.064 (4) | 0.054 (4) | 0.038 (3) | 0.011 (4) | 0.021 (3) | 0.012 (3) |
C5 | 0.069 (4) | 0.057 (4) | 0.068 (4) | 0.013 (4) | 0.024 (3) | 0.003 (3) |
C6 | 0.054 (4) | 0.034 (3) | 0.054 (3) | 0.013 (3) | 0.012 (3) | 0.003 (3) |
C7 | 0.061 (4) | 0.027 (3) | 0.046 (3) | 0.010 (3) | 0.020 (3) | 0.008 (3) |
C8 | 0.057 (4) | 0.042 (4) | 0.086 (4) | 0.015 (4) | 0.024 (3) | 0.005 (3) |
C9 | 0.091 (6) | 0.034 (4) | 0.102 (5) | 0.010 (4) | 0.051 (5) | 0.008 (4) |
C10 | 0.069 (5) | 0.048 (5) | 0.109 (5) | 0.017 (4) | 0.028 (4) | 0.011 (4) |
C11 | 0.065 (5) | 0.052 (4) | 0.115 (5) | 0.016 (4) | 0.045 (4) | 0.005 (4) |
C12 | 0.071 (5) | 0.035 (4) | 0.085 (4) | 0.009 (4) | 0.035 (4) | 0.007 (3) |
C13 | 0.068 (5) | 0.037 (4) | 0.060 (4) | 0.014 (4) | 0.017 (4) | 0.001 (3) |
C14 | 0.096 (5) | 0.044 (4) | 0.072 (4) | 0.017 (4) | 0.029 (4) | 0.005 (3) |
C15 | 0.140 (8) | 0.054 (5) | 0.069 (5) | 0.007 (5) | 0.001 (5) | −0.023 (4) |
C16 | 0.183 (11) | 0.074 (6) | 0.071 (5) | 0.055 (7) | 0.047 (6) | −0.011 (5) |
C17 | 0.147 (8) | 0.076 (6) | 0.078 (5) | 0.029 (6) | 0.057 (5) | −0.003 (5) |
C18 | 0.100 (6) | 0.054 (4) | 0.078 (5) | 0.023 (4) | 0.039 (4) | 0.008 (4) |
C19 | 0.061 (4) | 0.027 (3) | 0.047 (3) | 0.010 (3) | 0.018 (3) | 0.001 (3) |
N20 | 0.043 (3) | 0.044 (3) | 0.054 (3) | 0.004 (3) | 0.013 (2) | 0.004 (2) |
C21 | 0.053 (4) | 0.045 (4) | 0.049 (3) | 0.006 (3) | 0.019 (3) | −0.002 (3) |
N22 | 0.052 (3) | 0.040 (3) | 0.057 (3) | −0.004 (3) | 0.022 (3) | 0.007 (2) |
C23 | 0.060 (4) | 0.031 (3) | 0.049 (3) | 0.006 (3) | 0.009 (3) | −0.005 (3) |
O24 | 0.075 (3) | 0.052 (3) | 0.066 (2) | −0.006 (2) | 0.036 (2) | 0.009 (2) |
O25 | 0.067 (3) | 0.088 (3) | 0.048 (2) | 0.004 (3) | 0.015 (2) | 0.019 (2) |
O26 | 0.052 (3) | 0.070 (3) | 0.076 (3) | −0.011 (3) | 0.014 (2) | 0.001 (2) |
O27 | 0.060 (3) | 0.041 (3) | 0.073 (2) | 0.014 (2) | 0.019 (2) | −0.004 (2) |
C28 | 0.130 (7) | 0.053 (5) | 0.123 (5) | 0.021 (5) | 0.061 (5) | 0.020 (4) |
O29 | 0.073 (3) | 0.081 (3) | 0.075 (3) | 0.008 (3) | 0.027 (3) | 0.015 (3) |
C30 | 0.088 (5) | 0.104 (6) | 0.076 (4) | −0.012 (5) | 0.021 (4) | −0.014 (5) |
OW | 0.085 (3) | 0.057 (3) | 0.079 (3) | −0.019 (3) | 0.018 (2) | −0.003 (2) |
C1—C19 | 1.498 (7) | C13—C14 | 1.360 (8) |
C1—C23 | 1.545 (7) | C13—C18 | 1.390 (8) |
C1—C2 | 1.575 (7) | C14—C15 | 1.416 (8) |
C1—C6 | 1.589 (6) | C14—H14 | 0.9300 |
C2—C3 | 1.471 (7) | C15—C16 | 1.364 (10) |
C2—C13 | 1.525 (7) | C15—H15 | 0.9300 |
C2—H2 | 0.9800 | C16—C17 | 1.353 (10) |
C3—C4 | 1.497 (7) | C16—H16 | 0.9300 |
C3—H3A | 0.9700 | C17—C18 | 1.385 (8) |
C3—H3B | 0.9700 | C17—H17 | 0.9300 |
C4—O29 | 1.367 (6) | C18—H18 | 0.9300 |
C4—O27 | 1.471 (6) | C19—O24 | 1.228 (6) |
C4—C5 | 1.541 (7) | C19—N20 | 1.370 (6) |
C5—C6 | 1.473 (6) | N20—C21 | 1.394 (6) |
C5—H5A | 0.9700 | N20—H20 | 0.8600 |
C5—H5B | 0.9700 | C21—O25 | 1.208 (5) |
C6—C7 | 1.529 (7) | C21—N22 | 1.341 (6) |
C6—H6 | 0.9800 | N22—C23 | 1.379 (6) |
C7—C12 | 1.375 (7) | N22—H22 | 0.8600 |
C7—C8 | 1.376 (7) | C23—O26 | 1.202 (6) |
C8—C9 | 1.416 (7) | O27—C28 | 1.443 (6) |
C8—H8 | 0.9300 | C28—H28A | 0.9600 |
C9—C10 | 1.343 (8) | C28—H28B | 0.9600 |
C9—H9 | 0.9300 | C28—H28C | 0.9600 |
C10—C11 | 1.371 (8) | O29—C30 | 1.428 (6) |
C10—H10 | 0.9300 | C30—H30A | 0.9600 |
C11—C12 | 1.355 (7) | C30—H30B | 0.9600 |
C11—H11 | 0.9300 | C30—H30C | 0.9600 |
C12—H12 | 0.9300 | ||
C19—C1—C23 | 113.9 (4) | C7—C12—C11 | 122.5 (6) |
C19—C1—C2 | 106.3 (4) | C7—C12—H12 | 118.8 |
C23—C1—C2 | 109.9 (4) | C11—C12—H12 | 118.8 |
C19—C1—C6 | 108.3 (4) | C14—C13—C18 | 117.0 (6) |
C23—C1—C6 | 110.4 (4) | C14—C13—C2 | 120.2 (6) |
C2—C1—C6 | 107.9 (4) | C18—C13—C2 | 122.7 (6) |
C3—C2—C13 | 115.6 (5) | C13—C14—C15 | 121.4 (7) |
C3—C2—C1 | 114.1 (5) | C13—C14—H14 | 119.3 |
C13—C2—C1 | 110.3 (4) | C15—C14—H14 | 119.3 |
C3—C2—H2 | 105.2 | C16—C15—C14 | 120.0 (8) |
C13—C2—H2 | 105.2 | C16—C15—H15 | 120.0 |
C1—C2—H2 | 105.2 | C14—C15—H15 | 120.0 |
C2—C3—C4 | 115.0 (5) | C15—C16—C17 | 119.1 (8) |
C2—C3—H3A | 108.5 | C15—C16—H16 | 120.4 |
C4—C3—H3A | 108.5 | C17—C16—H16 | 120.4 |
C2—C3—H3B | 108.5 | C16—C17—C18 | 120.9 (8) |
C4—C3—H3B | 108.5 | C16—C17—H17 | 119.6 |
H3A—C3—H3B | 107.5 | C18—C17—H17 | 119.6 |
O29—C4—O27 | 110.1 (4) | C13—C18—C17 | 121.6 (7) |
O29—C4—C3 | 107.9 (5) | C13—C18—H18 | 119.2 |
O27—C4—C3 | 111.7 (5) | C17—C18—H18 | 119.2 |
O29—C4—C5 | 112.8 (5) | O24—C19—N20 | 119.1 (5) |
O27—C4—C5 | 102.6 (5) | O24—C19—C1 | 121.9 (5) |
C3—C4—C5 | 111.8 (4) | N20—C19—C1 | 119.0 (5) |
C6—C5—C4 | 113.8 (5) | C19—N20—C21 | 126.6 (5) |
C6—C5—H5A | 108.8 | C19—N20—H20 | 116.7 |
C4—C5—H5A | 108.8 | C21—N20—H20 | 116.7 |
C6—C5—H5B | 108.8 | O25—C21—N22 | 125.3 (6) |
C4—C5—H5B | 108.8 | O25—C21—N20 | 120.6 (5) |
H5A—C5—H5B | 107.7 | N22—C21—N20 | 114.2 (5) |
C5—C6—C7 | 113.6 (5) | C21—N22—C23 | 129.6 (5) |
C5—C6—C1 | 115.5 (4) | C21—N22—H22 | 115.2 |
C7—C6—C1 | 112.0 (4) | C23—N22—H22 | 115.2 |
C5—C6—H6 | 104.8 | O26—C23—N22 | 120.4 (6) |
C7—C6—H6 | 104.8 | O26—C23—C1 | 123.3 (5) |
C1—C6—H6 | 104.8 | N22—C23—C1 | 116.3 (5) |
C12—C7—C8 | 117.6 (5) | C4—O27—C28 | 115.8 (5) |
C12—C7—C6 | 121.0 (5) | O27—C28—H28A | 109.5 |
C8—C7—C6 | 121.4 (5) | O27—C28—H28B | 109.5 |
C7—C8—C9 | 119.8 (6) | H28A—C28—H28B | 109.5 |
C7—C8—H8 | 120.1 | O27—C28—H28C | 109.5 |
C9—C8—H8 | 120.1 | H28A—C28—H28C | 109.5 |
C10—C9—C8 | 120.2 (7) | H28B—C28—H28C | 109.5 |
C10—C9—H9 | 119.9 | C4—O29—C30 | 118.4 (5) |
C8—C9—H9 | 119.9 | O29—C30—H30A | 109.5 |
C9—C10—C11 | 120.0 (7) | O29—C30—H30B | 109.5 |
C9—C10—H10 | 120.0 | H30A—C30—H30B | 109.5 |
C11—C10—H10 | 120.0 | O29—C30—H30C | 109.5 |
C10—C11—C12 | 119.9 (6) | H30A—C30—H30C | 109.5 |
C10—C11—H11 | 120.1 | H30B—C30—H30C | 109.5 |
C12—C11—H11 | 120.1 | ||
C19—C1—C2—C3 | −165.0 (5) | C3—C2—C13—C18 | −46.1 (8) |
C23—C1—C2—C3 | 71.4 (6) | C1—C2—C13—C18 | 85.3 (7) |
C6—C1—C2—C3 | −49.0 (6) | C18—C13—C14—C15 | 2.6 (8) |
C19—C1—C2—C13 | 62.9 (6) | C2—C13—C14—C15 | 178.9 (5) |
C23—C1—C2—C13 | −60.8 (6) | C13—C14—C15—C16 | −3.2 (10) |
C6—C1—C2—C13 | 178.8 (5) | C14—C15—C16—C17 | 3.0 (12) |
C13—C2—C3—C4 | −176.8 (5) | C15—C16—C17—C18 | −2.4 (12) |
C1—C2—C3—C4 | 53.7 (7) | C14—C13—C18—C17 | −2.1 (9) |
C2—C3—C4—O29 | −175.8 (5) | C2—C13—C18—C17 | −178.2 (5) |
C2—C3—C4—O27 | 63.2 (6) | C16—C17—C18—C13 | 2.0 (10) |
C2—C3—C4—C5 | −51.2 (7) | C23—C1—C19—O24 | −177.3 (4) |
O29—C4—C5—C6 | 170.5 (4) | C2—C1—C19—O24 | 61.5 (6) |
O27—C4—C5—C6 | −71.1 (5) | C6—C1—C19—O24 | −54.1 (6) |
C3—C4—C5—C6 | 48.7 (7) | C23—C1—C19—N20 | 4.4 (7) |
C4—C5—C6—C7 | 179.0 (5) | C2—C1—C19—N20 | −116.8 (5) |
C4—C5—C6—C1 | −49.5 (6) | C6—C1—C19—N20 | 127.6 (5) |
C19—C1—C6—C5 | 162.6 (5) | O24—C19—N20—C21 | 173.8 (5) |
C23—C1—C6—C5 | −72.1 (6) | C1—C19—N20—C21 | −7.8 (7) |
C2—C1—C6—C5 | 48.0 (6) | C19—N20—C21—O25 | −174.8 (5) |
C19—C1—C6—C7 | −65.1 (6) | C19—N20—C21—N22 | 5.5 (7) |
C23—C1—C6—C7 | 60.2 (6) | O25—C21—N22—C23 | −179.5 (5) |
C2—C1—C6—C7 | −179.7 (5) | N20—C21—N22—C23 | 0.1 (7) |
C5—C6—C7—C12 | −126.8 (5) | C21—N22—C23—O26 | 178.0 (5) |
C1—C6—C7—C12 | 100.0 (6) | C21—N22—C23—C1 | −2.7 (7) |
C5—C6—C7—C8 | 54.5 (7) | C19—C1—C23—O26 | 179.6 (5) |
C1—C6—C7—C8 | −78.7 (6) | C2—C1—C23—O26 | −61.3 (6) |
C12—C7—C8—C9 | −1.5 (8) | C6—C1—C23—O26 | 57.6 (7) |
C6—C7—C8—C9 | 177.2 (5) | C19—C1—C23—N22 | 0.3 (6) |
C7—C8—C9—C10 | 1.6 (9) | C2—C1—C23—N22 | 119.4 (5) |
C8—C9—C10—C11 | −0.6 (10) | C6—C1—C23—N22 | −121.8 (4) |
C9—C10—C11—C12 | −0.3 (10) | O29—C4—O27—C28 | −60.4 (6) |
C8—C7—C12—C11 | 0.5 (8) | C3—C4—O27—C28 | 59.4 (6) |
C6—C7—C12—C11 | −178.2 (5) | C5—C4—O27—C28 | 179.3 (5) |
C10—C11—C12—C7 | 0.4 (10) | O27—C4—O29—C30 | −62.1 (6) |
C3—C2—C13—C14 | 137.8 (6) | C3—C4—O29—C30 | 175.8 (5) |
C1—C2—C13—C14 | −90.8 (6) | C5—C4—O29—C30 | 51.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N20—H20···OWi | 0.86 | 2.10 | 2.897 (6) | 154 |
N22—H22···O27ii | 0.86 | 2.13 | 2.984 (6) | 170 |
C3—H3A···O26 | 0.97 | 2.50 | 3.087 (7) | 119 |
C30—H30C···O26iii | 0.96 | 2.60 | 3.517 (9) | 160 |
C16—H16···Cg3ii | 0.93 | 3.06 | 3.51 | 112 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H24N2O5·H2O |
Mr | 426.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.559 (2), 10.755 (2), 15.346 (4) |
β (°) | 114.10 (1) |
V (Å3) | 2193.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.60 × 0.55 × 0.50 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5812, 4726, 1053 |
Rint | 0.096 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.192, 0.74 |
No. of reflections | 4726 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.20 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and ORTEP92 (Vicković, 1994), SHELXL97 and PARST (Nardelli, 1983).
D—H···A | D—H | H···A | D···A | D—H···A |
N20—H20···OWi | 0.86 | 2.10 | 2.897 (6) | 154 |
N22—H22···O27ii | 0.86 | 2.13 | 2.984 (6) | 170 |
C3—H3A···O26 | 0.97 | 2.50 | 3.087 (7) | 119 |
C30—H30C···O26iii | 0.96 | 2.60 | 3.517 (9) | 160 |
C16—H16···Cg3ii | 0.93 | 3.06 | 3.51 | 112 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2. |
Spiro compounds are biologically important because of the diverse nature of their medicinal properties. Pyrimidine derivatives are widely used in antiviral chemotherapy. A series of spiro-pyrimidine nucleoside analogues, such as [2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino- 1'',2''-oxathiole-2'',2''-dioxide)]pyrimidine Please clarify this name (TSAO), were found to inhibit human immunodeficiency virus type 1 (HIV-1) replication at a concentration of 0.06–0.8 µM, but were not cytotoxic at a 1000- to 10000-fold higher concentration (Reference?). These derivatives were also found to be effective against various HIV-2, Simian immunodeficiency virus, Moloney murine sarcoma virus, or other RNA or DNA viruses (Reference?), and they have proved to be highly specific inhibitors of the RNA-dependent DNA-polymerase function of the HIV-1 reverse transcriptase enzyme (Balzarini et al., 1992).
The cyclohexane triones are a novel group of synthetic antibacterial agents, which are active against the gram-positive bacteria Haemophilus influenzae and Mycobacterium smegmatis. In general, these compounds behave in a manner similar to that of hexachlorophene, inhibiting the transport of low molecular weight hydrophilic substances into bacteria. They may express more than one type of antibacterial effect (Lloyd et al., 1988).
Spiro-pyrimidinetriones containing the barbituric acid moiety exhibit a broad spectrum of chemotherapeutic properties, such as hypnotic, antitumour, antiviral, anticonvulsant, analgesic and toxic properties. They possess bacteriostatic, antidiabetic, antiarrhythmic and anti-inflammatory properties, and have been found to possess antifungal activity against Staphylococcus aureus, Bacillus subtilis and Pseudomonas vulgaris (Bhasker Reddy et al., 1992). Against this background, the crystal structure of the title compound, (I), has been determined and the results are presented here. \sch
The bond lengths in (I) involving atoms C2 and C6 are a little abnormal, but a similar situation has been observed in related structures (Toupet & Messager, 1983). This may be due to steric repulsion between the cyclohexane ring and the phenyl substituents at the C2 and C6 positions. Other than this, the bond lengths and angles in (I) are normal (Allen et al., 1987).
The cyclohexane ring adopts a chair conformation, with atoms C1 and C4 deviating from the best plane by 0.632 (3) and -0.595 (3) Å, respectively. This is confirmed by the puckering amplitude QT = 0.5045 (Nardelli, 1983). The two phenyl rings (A and B) and the pyrimidine ring are planar, and the phenyl rings are oriented at an angle of 68.9 (1)° to each other. The phenyl rings A and B are oriented at 65.8 (1) and 58.9 (1)°, respectively, from the best plane of the cyclohexane ring. The pyrimidine ring and the best plane of the cyclohexane ring are approximately perpendicular to each other, which is evidenced from the orientation angle of 89.0 (1)°. This is in agreement with the theoretical conclusion for most spiro compounds (Finar, 1985). The two phenyl rings have an equatorial orientation and the corresponding torsion angles are C13—C2—C3—C4 - 176.2 (3)° and C4—C5—C6—C7 179.0 (3)°.
An interesting weak intramolecular π–π interaction occurs between the pyrimidine and phenyl rings, with a Cg···Cg distance (Cg is the ring centroid) of 3.9019 Å (α = 59.54°) for ring A and 3.7088 Å (α = 52.03°) for ring B (Jorgensen & Severance, 1990; Hunter & Sanders, 1990; Desiraju, 1989). In addition to this, one of the phenyl rings also participates in an intermolecular C—H···π interaction, between atom C16 and the terminal C30 atom (Desiraju, 1989).
The water molecule of (I) interacts with the pyrimidinetrione ring, making a strong intermolecular hydrogen bond with atom N20 and intermolecular interactions with atoms O24 and O25, the contact distance of which is less than the sum of the van der Waals radii, which stabilize the crystal packing. The other N atom (N22) of the pyrimidinetrione ring is involved in an intermolecular hydrogen bond with the carboxyl O atom (O27). In addition to this, there are some weak C—H···O-type intra- and intermolecular interactions which stabilize the structure.
The packing of the molecule of (I) viewed down the b axis is shown in Fig. 2. The molecules are packed in a discrete fashion, and are stabilized by van der Waals forces in addition to the above-mentioned interactions.