organic compounds
N,N-Diethylanilinium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate
aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
*Correspondence e-mail: kalaivbalaj@yahoo.co.in
The 10H16N+·C10H5N4O7− (trivial name: N,N-diethylanilinium 2,4-dinitrophenylbarbiturate), comprises two anion–cation units. In the anions, the dinitrophenyl ring and the mean plane of the barbiturate ring [planar to within 0.011 (2) and 0.023 (2) Å in the two anions] are inclined to one another by 41.47 (9) and 45.12 (9)°. In the crystal, the anions are linked via strong N—H⋯O hydrogen bonds, forming chains propagating along [10-1]. Within the chains, adjacent inversion-related anionic barbiturate entities are joined through R22(8) ring motifs. The cations are linked to the chains via N—H⋯O hydrogen bonds. The chains are linked via a number of C—H⋯O interactions, forming a three-dimensional structure.
of the title molecular salt, CRelated literature
For the crystal structures of related ); Buvaneswari & Kalaivani (2011a,b); Kalaivani et al. (2012); Babykala & Kalaivani (2012). For the biological activity of see: Hueso et al. (2003); Kalaivani et al. (2008); Tripathi (2009); Kalaivani & Buvaneswari (2010).
see: Kalaivani & Malarvizhi (2009Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S160053681204874X/su2535sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681204874X/su2535Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681204874X/su2535Isup3.cml
Analytical grade 1-chloro-2,4-dinitrobenzene (2.02 g, 0.01 mol) was dissolved in 20 ml of absolute alcohol. Barbituric acid (1.28 g, 0.01 mol) was also dissolved in 30 ml of absolute alcohol separately. These two solutions were then mixed well. To this mixture, ca. 4 ml of N,N-diethylaniine (0.03 mol) was added and shaken well for 5–6 hrs. The slightly turbid solution obtained was filtered and kept as such at room temperature. After a period of four weeks, dark shiny maroon red coloured crystals of the title salt crystallized out from this solution. The crystals were filtered and washed well with 30 ml of dry ether. The crystals were then powdered and washed with 5 ml of absolute alcohol to remove the unreacted reactants and finally with 25 ml of dry ether. The pure powder was then recrystallized from hot ethanol (M.p: 481 K; yield: 80%). Good quality single crystals, suitable for X-ray diffraction studies, were obtained by slow evaporation of a solution in ethanol at room temperature. The crystals obtained were non-hygroscopic and extraordinarily stable at room temperature.
The N-bound H atoms were located in a difference
and refind with a N-H distance restraint of 0.90 (2) Å. The C-bound hydrogen atoms were placed in calculated positions and refined as riding atoms: C—H = 0.93, 0.97 and 0.96 Å for CH, CH2 and CH3 H atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H atoms and = 1.2 for other H atoms.The methylene group of barbituric acid [a pyrimidine derivative] is flanked on both sides by the electron-withdrawing carbonyl groups which makes the hydrogen atoms highly acidic. These acidic H atoms have been targeted by our group in the preparation of a number of extraordinarily stable
(Kalaivani & Malarvizhi, 2009; Buvaneswari & Kalaivani, 2011a; Kalaivani et al., 2012; Babykala & Kalaivani, 2012). We have reported on the of a barbiturate related to the title molecular salt but derived from 1-chloro-2,4,6-trinitrobenzene (TNCB) and barbituric acid in the presence of N,N-diethylaniline (I) (Buvaneswari & Kalaivani, 2011b). Herein we report on the of the new title molecular salt obtained from 1-chloro-2,4-dinitrobenzene (DNCB) and barbituric acid in the presence of N,N-diethylaniline, (II).Unlike the 1.
of the related reported barbiturate (I), which comprises of only one anion and cation moieties, the of the barbiturate of the title compound (II) is composed of two cations and two anions (Fig. 1). Contrary to the barbiturate of TNCB (I), which crystallized in the monoclinic P21/c, the title compound (II) crystallized in the triclinic PIn the crystal of (II), the anions are linked via N—H···O hydrogen bonds (Table 1 and Fig. 2), forming chains along direction [1 0 -1]. This linkage and the R22(8) ring motifs formed between inversion-related barbiturate residues contributes considerably to the extraordinary stability of the title molecular salt. The cations are linked to the chains via N-H···O hydrogen bonds (Table 1 and Fig. 2). There are C-H···O interactions present (Table 1) but no π-π stacking interactions between the N,N-diethylaniline and 2,4-dinitrophenyl ring moieties.
As
are employed in the treatment of neurological disorders (Hueso et al., 2003; Kalaivani et al., 2008; Tripathi, 2009; Kalaivani & Buvaneswari, 2010), the non-bonding interactions of the present investigation may help to understand the mechanistic aspects of the physiological action of barbiturates.For the crystal structures of related
see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011a,b); Kalaivani et al. (2012); Babykala & Kalaivani (2012). For the biological activity of see: Hueso et al. (2003); Kalaivani et al. (2008); Tripathi (2009); Kalaivani & Buvaneswari (2010).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. A view of the molecular structure of the title compound, with the numbering scheme. Displacement ellipsoids are drawn at the 30% probability. | |
Fig. 2. A partial view of the crystal packing of the title compound with the N-H···O hydrogen bonds shown as dashed lines (see Table 1 for details). |
C10H16N+·C10H5N4O7− | Z = 4 |
Mr = 443.42 | F(000) = 928 |
Triclinic, P1 | Dx = 1.392 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7260 (2) Å | Cell parameters from 5648 reflections |
b = 14.2930 (3) Å | θ = 2.4–24.5° |
c = 18.1080 (5) Å | µ = 0.11 mm−1 |
α = 106.712 (1)° | T = 293 K |
β = 96.490 (1)° | Block, red |
γ = 97.667 (1)° | 0.30 × 0.30 × 0.25 mm |
V = 2116.27 (9) Å3 |
Bruker Kappa APEXII CCD diffractometer | 7482 independent reflections |
Radiation source: fine-focus sealed tube | 5563 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω and φ scan | θmax = 25.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
Tmin = 0.944, Tmax = 0.996 | k = −17→16 |
36083 measured reflections | l = −20→21 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.687P] where P = (Fo2 + 2Fc2)/3 |
7482 reflections | (Δ/σ)max < 0.001 |
601 parameters | Δρmax = 0.39 e Å−3 |
6 restraints | Δρmin = −0.21 e Å−3 |
C10H16N+·C10H5N4O7− | γ = 97.667 (1)° |
Mr = 443.42 | V = 2116.27 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.7260 (2) Å | Mo Kα radiation |
b = 14.2930 (3) Å | µ = 0.11 mm−1 |
c = 18.1080 (5) Å | T = 293 K |
α = 106.712 (1)° | 0.30 × 0.30 × 0.25 mm |
β = 96.490 (1)° |
Bruker Kappa APEXII CCD diffractometer | 7482 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5563 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.996 | Rint = 0.029 |
36083 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 6 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.39 e Å−3 |
7482 reflections | Δρmin = −0.21 e Å−3 |
601 parameters |
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 esds 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.2543 (2) | 0.83264 (13) | 0.37167 (12) | 0.0880 (8) | |
O2 | 1.2930 (2) | 0.83537 (15) | 0.25658 (14) | 0.0970 (9) | |
O3 | 0.8629 (3) | 0.96777 (15) | 0.15034 (12) | 0.0945 (8) | |
O4 | 0.6274 (2) | 0.91507 (15) | 0.16287 (13) | 0.1024 (9) | |
O5 | 0.80556 (18) | 0.67237 (12) | 0.42022 (9) | 0.0670 (6) | |
O6 | 1.19736 (17) | 0.62862 (11) | 0.26121 (8) | 0.0571 (5) | |
O7 | 1.14127 (16) | 0.46411 (10) | 0.43867 (8) | 0.0542 (5) | |
N1 | 1.2085 (2) | 0.82324 (14) | 0.30347 (14) | 0.0665 (8) | |
N2 | 0.7678 (3) | 0.91628 (15) | 0.17346 (12) | 0.0725 (8) | |
N3 | 0.97818 (18) | 0.57160 (12) | 0.42827 (9) | 0.0438 (5) | |
N4 | 1.16646 (19) | 0.54767 (11) | 0.35010 (9) | 0.0419 (5) | |
C1 | 1.0386 (2) | 0.80155 (14) | 0.27732 (11) | 0.0463 (6) | |
C2 | 0.9841 (3) | 0.86114 (15) | 0.23618 (12) | 0.0535 (7) | |
C3 | 0.8257 (3) | 0.85337 (15) | 0.21745 (12) | 0.0532 (7) | |
C4 | 0.7220 (3) | 0.78816 (16) | 0.23815 (12) | 0.0573 (8) | |
C5 | 0.7796 (2) | 0.72705 (16) | 0.27701 (12) | 0.0523 (7) | |
C6 | 0.9407 (2) | 0.73108 (14) | 0.29834 (10) | 0.0422 (6) | |
C7 | 0.9959 (2) | 0.66156 (13) | 0.33636 (10) | 0.0412 (6) | |
C8 | 0.9205 (2) | 0.63875 (14) | 0.39476 (11) | 0.0442 (6) | |
C9 | 1.0979 (2) | 0.52410 (13) | 0.40734 (10) | 0.0399 (6) | |
C10 | 1.1233 (2) | 0.61515 (13) | 0.31275 (10) | 0.0413 (6) | |
O8 | 0.8547 (2) | 0.19291 (16) | 0.43667 (11) | 0.0935 (8) | |
O9 | 0.8049 (3) | 0.06694 (16) | 0.33392 (12) | 0.1072 (9) | |
O10 | 0.37682 (18) | 0.18846 (12) | 0.11714 (9) | 0.0671 (6) | |
O11 | 0.5594 (2) | 0.10258 (12) | 0.08857 (9) | 0.0751 (6) | |
O12 | 0.64772 (16) | 0.31204 (10) | 0.07995 (8) | 0.0498 (5) | |
O13 | 0.41243 (16) | 0.57389 (10) | 0.07773 (8) | 0.0517 (5) | |
O14 | 0.43352 (18) | 0.48055 (12) | 0.29694 (8) | 0.0619 (6) | |
N5 | 0.8058 (2) | 0.15384 (18) | 0.36769 (12) | 0.0688 (8) | |
N6 | 0.5070 (2) | 0.16896 (13) | 0.13139 (10) | 0.0517 (6) | |
N7 | 0.53330 (17) | 0.44455 (11) | 0.08224 (9) | 0.0391 (5) | |
N8 | 0.42292 (18) | 0.52477 (12) | 0.18645 (9) | 0.0436 (5) | |
C11 | 0.7437 (2) | 0.21443 (16) | 0.32261 (12) | 0.0510 (7) | |
C12 | 0.6703 (2) | 0.16833 (15) | 0.24722 (12) | 0.0487 (7) | |
C13 | 0.6020 (2) | 0.22549 (14) | 0.20738 (10) | 0.0416 (6) | |
C14 | 0.6105 (2) | 0.32753 (14) | 0.23874 (10) | 0.0401 (6) | |
C15 | 0.6879 (2) | 0.36932 (16) | 0.31568 (11) | 0.0514 (7) | |
C16 | 0.7528 (2) | 0.31432 (17) | 0.35756 (12) | 0.0558 (8) | |
C17 | 0.5522 (2) | 0.39040 (13) | 0.19505 (10) | 0.0393 (6) | |
C18 | 0.58097 (19) | 0.37731 (13) | 0.11825 (10) | 0.0376 (6) | |
C19 | 0.4529 (2) | 0.51796 (13) | 0.11341 (10) | 0.0389 (6) | |
C20 | 0.4700 (2) | 0.46523 (14) | 0.23091 (10) | 0.0425 (6) | |
N9 | 0.90805 (19) | 0.23135 (12) | 0.04844 (9) | 0.0474 (5) | |
C21 | 0.9873 (2) | 0.28472 (14) | 0.00108 (11) | 0.0453 (6) | |
C22 | 1.1413 (2) | 0.27955 (18) | −0.00719 (12) | 0.0605 (8) | |
C23 | 1.2100 (3) | 0.3305 (2) | −0.05289 (14) | 0.0753 (9) | |
C24 | 1.1257 (3) | 0.38406 (19) | −0.08902 (14) | 0.0756 (10) | |
C25 | 0.9732 (3) | 0.38696 (18) | −0.08093 (14) | 0.0700 (9) | |
C26 | 0.9028 (3) | 0.33770 (16) | −0.03520 (12) | 0.0557 (7) | |
C27 | 0.9959 (3) | 0.2525 (2) | 0.12914 (14) | 0.0719 (9) | |
C28 | 1.0290 (4) | 0.3602 (2) | 0.17372 (16) | 0.0997 (13) | |
C29 | 0.8655 (3) | 0.12146 (17) | 0.00675 (17) | 0.0765 (10) | |
C30 | 0.7452 (4) | 0.0983 (2) | −0.06477 (17) | 0.1068 (14) | |
N10 | 0.3631 (2) | 0.20996 (15) | 0.50188 (11) | 0.0603 (7) | |
C31 | 0.3160 (3) | 0.17238 (16) | 0.41624 (13) | 0.0587 (8) | |
C32 | 0.3835 (4) | 0.10006 (19) | 0.37113 (17) | 0.0839 (11) | |
C33 | 0.3349 (4) | 0.0697 (2) | 0.28871 (18) | 0.0924 (13) | |
C34 | 0.2279 (5) | 0.1152 (3) | 0.2591 (2) | 0.1064 (16) | |
C35 | 0.1642 (4) | 0.1859 (3) | 0.30427 (19) | 0.1081 (14) | |
C36 | 0.2082 (3) | 0.2158 (2) | 0.38384 (15) | 0.0749 (10) | |
C37 | 0.5166 (3) | 0.2857 (2) | 0.52637 (16) | 0.0776 (10) | |
C38 | 0.5019 (3) | 0.3733 (2) | 0.49872 (17) | 0.0838 (10) | |
C39 | 0.3632 (4) | 0.1319 (2) | 0.54130 (18) | 0.0955 (14) | |
C40 | 0.2051 (5) | 0.0682 (2) | 0.5247 (2) | 0.1146 (18) | |
H2 | 1.05320 | 0.90540 | 0.22160 | 0.0640* | |
H3A | 0.932 (2) | 0.5593 (14) | 0.4664 (10) | 0.051 (5)* | |
H4 | 0.61460 | 0.78520 | 0.22620 | 0.0690* | |
H4A | 1.2469 (19) | 0.5216 (14) | 0.3346 (11) | 0.045 (5)* | |
H5 | 0.70910 | 0.68140 | 0.28960 | 0.0630* | |
H7A | 0.550 (2) | 0.4353 (14) | 0.0340 (9) | 0.045 (5)* | |
H8A | 0.361 (2) | 0.5667 (13) | 0.2072 (11) | 0.052 (6)* | |
H12 | 0.66660 | 0.10090 | 0.22360 | 0.0580* | |
H15 | 0.69560 | 0.43710 | 0.33940 | 0.0620* | |
H16 | 0.80230 | 0.34420 | 0.40890 | 0.0670* | |
H9A | 0.8194 (19) | 0.2558 (14) | 0.0571 (11) | 0.051 (6)* | |
H22 | 1.19750 | 0.24290 | 0.01730 | 0.0730* | |
H23 | 1.31390 | 0.32830 | −0.05920 | 0.0900* | |
H24 | 1.17320 | 0.41860 | −0.11920 | 0.0910* | |
H25 | 0.91630 | 0.42240 | −0.10640 | 0.0840* | |
H26 | 0.79900 | 0.34040 | −0.02900 | 0.0670* | |
H27A | 0.93530 | 0.21690 | 0.15740 | 0.0860* | |
H27B | 1.09420 | 0.22810 | 0.12550 | 0.0860* | |
H28A | 1.08570 | 0.36990 | 0.22470 | 0.1490* | |
H28B | 0.93200 | 0.38450 | 0.17870 | 0.1490* | |
H28C | 1.09050 | 0.39580 | 0.14650 | 0.1490* | |
H29A | 0.95900 | 0.09610 | −0.00800 | 0.0920* | |
H29B | 0.82530 | 0.08810 | 0.04210 | 0.0920* | |
H30A | 0.72210 | 0.02790 | −0.08970 | 0.1600* | |
H30B | 0.78490 | 0.13050 | −0.10020 | 0.1600* | |
H30C | 0.65140 | 0.12160 | −0.05020 | 0.1600* | |
H10A | 0.290 (2) | 0.2464 (16) | 0.5230 (13) | 0.074 (7)* | |
H32 | 0.45870 | 0.07160 | 0.39350 | 0.1000* | |
H33 | 0.37580 | 0.01960 | 0.25590 | 0.1110* | |
H34 | 0.19760 | 0.09640 | 0.20530 | 0.1280* | |
H35 | 0.09000 | 0.21490 | 0.28190 | 0.1300* | |
H36 | 0.16470 | 0.26560 | 0.41550 | 0.0900* | |
H37A | 0.54380 | 0.30760 | 0.58280 | 0.0930* | |
H37B | 0.60040 | 0.25420 | 0.50480 | 0.0930* | |
H38A | 0.59950 | 0.41900 | 0.51440 | 0.1260* | |
H38B | 0.42080 | 0.40560 | 0.52110 | 0.1260* | |
H38C | 0.47590 | 0.35180 | 0.44280 | 0.1260* | |
H39A | 0.39300 | 0.16300 | 0.59720 | 0.1140* | |
H39B | 0.43990 | 0.09100 | 0.52320 | 0.1140* | |
H40A | 0.20820 | 0.01830 | 0.55050 | 0.1720* | |
H40B | 0.17600 | 0.03700 | 0.46940 | 0.1720* | |
H40C | 0.12950 | 0.10850 | 0.54360 | 0.1720* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0757 (12) | 0.0802 (12) | 0.1037 (15) | 0.0067 (9) | −0.0243 (11) | 0.0390 (11) |
O2 | 0.0658 (11) | 0.1039 (14) | 0.160 (2) | 0.0252 (10) | 0.0406 (12) | 0.0874 (15) |
O3 | 0.1146 (16) | 0.0906 (13) | 0.1059 (15) | 0.0314 (12) | 0.0118 (12) | 0.0690 (12) |
O4 | 0.0853 (14) | 0.0965 (14) | 0.1368 (18) | 0.0291 (11) | −0.0221 (12) | 0.0629 (13) |
O5 | 0.0707 (10) | 0.0887 (11) | 0.0727 (10) | 0.0480 (9) | 0.0408 (8) | 0.0465 (9) |
O6 | 0.0749 (10) | 0.0678 (9) | 0.0581 (8) | 0.0416 (8) | 0.0374 (7) | 0.0418 (8) |
O7 | 0.0630 (9) | 0.0613 (9) | 0.0612 (9) | 0.0280 (7) | 0.0245 (7) | 0.0411 (7) |
N1 | 0.0558 (12) | 0.0570 (11) | 0.0991 (16) | 0.0148 (9) | 0.0068 (12) | 0.0431 (11) |
N2 | 0.0906 (16) | 0.0606 (12) | 0.0742 (13) | 0.0284 (12) | −0.0027 (12) | 0.0323 (11) |
N3 | 0.0509 (9) | 0.0515 (9) | 0.0431 (9) | 0.0198 (8) | 0.0200 (7) | 0.0266 (8) |
N4 | 0.0511 (9) | 0.0454 (9) | 0.0423 (9) | 0.0228 (8) | 0.0193 (7) | 0.0231 (7) |
C1 | 0.0506 (11) | 0.0448 (11) | 0.0501 (11) | 0.0180 (9) | 0.0094 (9) | 0.0200 (9) |
C2 | 0.0681 (14) | 0.0447 (11) | 0.0563 (12) | 0.0163 (10) | 0.0120 (10) | 0.0252 (10) |
C3 | 0.0683 (14) | 0.0487 (12) | 0.0497 (12) | 0.0265 (10) | 0.0037 (10) | 0.0212 (10) |
C4 | 0.0547 (12) | 0.0650 (14) | 0.0583 (13) | 0.0243 (11) | 0.0047 (10) | 0.0239 (11) |
C5 | 0.0523 (12) | 0.0597 (13) | 0.0541 (12) | 0.0178 (10) | 0.0119 (9) | 0.0267 (10) |
C6 | 0.0520 (11) | 0.0443 (10) | 0.0372 (10) | 0.0209 (9) | 0.0127 (8) | 0.0156 (8) |
C7 | 0.0484 (11) | 0.0434 (10) | 0.0395 (10) | 0.0183 (8) | 0.0125 (8) | 0.0182 (8) |
C8 | 0.0491 (11) | 0.0473 (11) | 0.0441 (10) | 0.0180 (9) | 0.0141 (9) | 0.0195 (9) |
C9 | 0.0467 (10) | 0.0402 (10) | 0.0368 (10) | 0.0103 (8) | 0.0089 (8) | 0.0159 (8) |
C10 | 0.0527 (11) | 0.0420 (10) | 0.0384 (10) | 0.0186 (9) | 0.0148 (8) | 0.0190 (8) |
O8 | 0.1209 (16) | 0.1173 (15) | 0.0613 (11) | 0.0487 (13) | 0.0022 (10) | 0.0489 (11) |
O9 | 0.171 (2) | 0.0839 (14) | 0.0872 (14) | 0.0622 (14) | 0.0039 (13) | 0.0465 (12) |
O10 | 0.0541 (9) | 0.0755 (10) | 0.0751 (11) | 0.0078 (8) | −0.0039 (8) | 0.0355 (9) |
O11 | 0.1078 (14) | 0.0542 (9) | 0.0626 (10) | 0.0280 (9) | 0.0105 (9) | 0.0120 (8) |
O12 | 0.0605 (8) | 0.0525 (8) | 0.0537 (8) | 0.0308 (7) | 0.0282 (7) | 0.0264 (7) |
O13 | 0.0647 (9) | 0.0573 (8) | 0.0543 (8) | 0.0329 (7) | 0.0253 (7) | 0.0340 (7) |
O14 | 0.0797 (10) | 0.0858 (11) | 0.0436 (8) | 0.0502 (9) | 0.0286 (7) | 0.0332 (8) |
N5 | 0.0785 (14) | 0.0865 (16) | 0.0638 (13) | 0.0372 (11) | 0.0154 (10) | 0.0462 (12) |
N6 | 0.0591 (11) | 0.0497 (10) | 0.0548 (10) | 0.0108 (8) | 0.0089 (9) | 0.0287 (9) |
N7 | 0.0459 (9) | 0.0447 (9) | 0.0385 (8) | 0.0187 (7) | 0.0171 (7) | 0.0221 (7) |
N8 | 0.0511 (9) | 0.0484 (9) | 0.0445 (9) | 0.0269 (8) | 0.0202 (7) | 0.0217 (7) |
C11 | 0.0501 (11) | 0.0688 (14) | 0.0513 (12) | 0.0250 (10) | 0.0127 (9) | 0.0370 (11) |
C12 | 0.0533 (12) | 0.0507 (11) | 0.0572 (12) | 0.0214 (9) | 0.0187 (10) | 0.0306 (10) |
C13 | 0.0418 (10) | 0.0513 (11) | 0.0414 (10) | 0.0145 (8) | 0.0114 (8) | 0.0245 (9) |
C14 | 0.0368 (10) | 0.0491 (11) | 0.0453 (10) | 0.0162 (8) | 0.0156 (8) | 0.0243 (9) |
C15 | 0.0572 (12) | 0.0542 (12) | 0.0485 (12) | 0.0193 (10) | 0.0077 (9) | 0.0204 (10) |
C16 | 0.0584 (13) | 0.0711 (15) | 0.0444 (11) | 0.0213 (11) | 0.0060 (9) | 0.0243 (11) |
C17 | 0.0411 (10) | 0.0439 (10) | 0.0425 (10) | 0.0155 (8) | 0.0140 (8) | 0.0216 (8) |
C18 | 0.0347 (9) | 0.0400 (10) | 0.0467 (10) | 0.0132 (8) | 0.0125 (8) | 0.0213 (8) |
C19 | 0.0392 (10) | 0.0427 (10) | 0.0433 (10) | 0.0132 (8) | 0.0141 (8) | 0.0209 (8) |
C20 | 0.0453 (10) | 0.0509 (11) | 0.0414 (10) | 0.0191 (9) | 0.0134 (8) | 0.0228 (9) |
N9 | 0.0442 (9) | 0.0537 (10) | 0.0499 (9) | 0.0174 (8) | 0.0119 (7) | 0.0191 (8) |
C21 | 0.0449 (11) | 0.0485 (11) | 0.0404 (10) | 0.0077 (9) | 0.0091 (8) | 0.0097 (9) |
C22 | 0.0441 (12) | 0.0820 (16) | 0.0523 (12) | 0.0099 (11) | 0.0069 (10) | 0.0165 (11) |
C23 | 0.0504 (13) | 0.102 (2) | 0.0544 (14) | −0.0132 (13) | 0.0140 (11) | 0.0044 (14) |
C24 | 0.091 (2) | 0.0739 (17) | 0.0516 (14) | −0.0166 (14) | 0.0174 (13) | 0.0151 (12) |
C25 | 0.0928 (19) | 0.0659 (15) | 0.0575 (14) | 0.0139 (13) | 0.0183 (13) | 0.0261 (12) |
C26 | 0.0603 (13) | 0.0615 (13) | 0.0520 (12) | 0.0188 (11) | 0.0152 (10) | 0.0220 (11) |
C27 | 0.0580 (14) | 0.112 (2) | 0.0587 (14) | 0.0186 (14) | 0.0075 (11) | 0.0452 (15) |
C28 | 0.091 (2) | 0.127 (3) | 0.0545 (16) | −0.0118 (18) | −0.0031 (14) | 0.0060 (17) |
C29 | 0.0864 (18) | 0.0517 (14) | 0.101 (2) | 0.0179 (13) | 0.0414 (16) | 0.0259 (14) |
C30 | 0.132 (3) | 0.084 (2) | 0.0719 (19) | −0.0339 (19) | 0.0237 (19) | −0.0054 (16) |
N10 | 0.0578 (11) | 0.0746 (13) | 0.0574 (11) | 0.0316 (10) | 0.0166 (9) | 0.0225 (10) |
C31 | 0.0650 (14) | 0.0558 (13) | 0.0570 (13) | 0.0094 (11) | 0.0233 (11) | 0.0153 (11) |
C32 | 0.105 (2) | 0.0655 (16) | 0.089 (2) | 0.0196 (15) | 0.0458 (17) | 0.0224 (15) |
C33 | 0.122 (3) | 0.0617 (17) | 0.081 (2) | −0.0132 (17) | 0.0552 (19) | 0.0007 (15) |
C34 | 0.110 (3) | 0.124 (3) | 0.072 (2) | −0.017 (2) | 0.0238 (19) | 0.023 (2) |
C35 | 0.103 (2) | 0.158 (3) | 0.0690 (19) | 0.021 (2) | 0.0096 (17) | 0.046 (2) |
C36 | 0.0685 (16) | 0.0980 (19) | 0.0624 (15) | 0.0187 (14) | 0.0091 (12) | 0.0300 (14) |
C37 | 0.0473 (13) | 0.105 (2) | 0.0712 (16) | 0.0150 (13) | 0.0035 (11) | 0.0143 (15) |
C38 | 0.0696 (16) | 0.0881 (19) | 0.0866 (19) | −0.0036 (14) | 0.0176 (14) | 0.0216 (16) |
C39 | 0.122 (3) | 0.106 (2) | 0.092 (2) | 0.059 (2) | 0.0330 (18) | 0.0587 (18) |
C40 | 0.175 (4) | 0.082 (2) | 0.110 (3) | 0.019 (2) | 0.051 (2) | 0.0563 (19) |
O1—N1 | 1.217 (3) | C14—C15 | 1.398 (3) |
O2—N1 | 1.219 (3) | C14—C17 | 1.460 (3) |
O3—N2 | 1.224 (3) | C15—C16 | 1.371 (3) |
O4—N2 | 1.216 (3) | C17—C20 | 1.411 (3) |
O5—C8 | 1.247 (2) | C17—C18 | 1.405 (2) |
O6—C10 | 1.238 (2) | C12—H12 | 0.9300 |
O7—C9 | 1.232 (2) | C15—H15 | 0.9300 |
O8—N5 | 1.212 (3) | C16—H16 | 0.9300 |
O9—N5 | 1.215 (3) | C21—C22 | 1.378 (3) |
O10—N6 | 1.222 (2) | C21—C26 | 1.369 (3) |
O11—N6 | 1.218 (2) | C22—C23 | 1.385 (4) |
O12—C18 | 1.247 (2) | C23—C24 | 1.373 (4) |
O13—C19 | 1.226 (2) | C24—C25 | 1.360 (4) |
O14—C20 | 1.238 (2) | C25—C26 | 1.376 (3) |
N1—C1 | 1.467 (3) | C27—C28 | 1.490 (4) |
N2—C3 | 1.463 (3) | C29—C30 | 1.497 (4) |
N3—C8 | 1.392 (3) | C22—H22 | 0.9300 |
N3—C9 | 1.352 (2) | C23—H23 | 0.9300 |
N4—C9 | 1.354 (2) | C24—H24 | 0.9300 |
N4—C10 | 1.394 (2) | C25—H25 | 0.9300 |
N3—H3A | 0.885 (18) | C26—H26 | 0.9300 |
N4—H4A | 0.874 (18) | C27—H27B | 0.9700 |
N5—C11 | 1.464 (3) | C27—H27A | 0.9700 |
N6—C13 | 1.469 (2) | C28—H28A | 0.9600 |
N7—C18 | 1.388 (2) | C28—H28B | 0.9600 |
N7—C19 | 1.363 (2) | C28—H28C | 0.9600 |
N8—C19 | 1.356 (2) | C29—H29A | 0.9700 |
N8—C20 | 1.398 (3) | C29—H29B | 0.9700 |
N7—H7A | 0.877 (16) | C30—H30B | 0.9600 |
N8—H8A | 0.892 (19) | C30—H30C | 0.9600 |
N9—C27 | 1.498 (3) | C30—H30A | 0.9600 |
N9—C29 | 1.508 (3) | C31—C32 | 1.367 (4) |
N9—C21 | 1.471 (3) | C31—C36 | 1.362 (4) |
N9—H9A | 0.902 (18) | C32—C33 | 1.425 (4) |
N10—C39 | 1.487 (4) | C33—C34 | 1.353 (5) |
N10—C31 | 1.477 (3) | C34—C35 | 1.333 (6) |
N10—C37 | 1.538 (3) | C35—C36 | 1.372 (4) |
N10—H10A | 0.92 (2) | C37—C38 | 1.491 (4) |
C1—C6 | 1.398 (3) | C39—C40 | 1.495 (5) |
C1—C2 | 1.378 (3) | C32—H32 | 0.9300 |
C2—C3 | 1.367 (4) | C33—H33 | 0.9300 |
C3—C4 | 1.371 (3) | C34—H34 | 0.9300 |
C4—C5 | 1.379 (3) | C35—H35 | 0.9300 |
C5—C6 | 1.404 (3) | C36—H36 | 0.9300 |
C6—C7 | 1.463 (3) | C37—H37A | 0.9700 |
C7—C10 | 1.414 (3) | C37—H37B | 0.9700 |
C7—C8 | 1.399 (3) | C38—H38A | 0.9600 |
C2—H2 | 0.9300 | C38—H38B | 0.9600 |
C4—H4 | 0.9300 | C38—H38C | 0.9600 |
C5—H5 | 0.9300 | C39—H39A | 0.9700 |
C11—C12 | 1.371 (3) | C39—H39B | 0.9700 |
C11—C16 | 1.373 (3) | C40—H40A | 0.9600 |
C12—C13 | 1.384 (3) | C40—H40B | 0.9600 |
C13—C14 | 1.393 (3) | C40—H40C | 0.9600 |
O1—N1—O2 | 124.8 (2) | C13—C12—H12 | 121.00 |
O1—N1—C1 | 117.30 (19) | C11—C12—H12 | 121.00 |
O2—N1—C1 | 117.8 (2) | C16—C15—H15 | 119.00 |
O3—N2—O4 | 123.8 (2) | C14—C15—H15 | 119.00 |
O3—N2—C3 | 118.5 (2) | C15—C16—H16 | 121.00 |
O4—N2—C3 | 117.7 (2) | C11—C16—H16 | 120.00 |
C8—N3—C9 | 125.43 (16) | C22—C21—C26 | 121.5 (2) |
C9—N4—C10 | 125.46 (16) | N9—C21—C26 | 118.04 (18) |
C9—N3—H3A | 117.8 (13) | N9—C21—C22 | 120.46 (18) |
C8—N3—H3A | 116.8 (13) | C21—C22—C23 | 118.2 (2) |
C9—N4—H4A | 120.5 (13) | C22—C23—C24 | 120.4 (2) |
C10—N4—H4A | 114.0 (13) | C23—C24—C25 | 120.4 (2) |
O9—N5—C11 | 118.1 (2) | C24—C25—C26 | 120.2 (2) |
O8—N5—O9 | 123.6 (2) | C21—C26—C25 | 119.3 (2) |
O8—N5—C11 | 118.3 (2) | N9—C27—C28 | 112.7 (2) |
O10—N6—C13 | 117.51 (17) | N9—C29—C30 | 112.1 (2) |
O11—N6—C13 | 118.07 (17) | C21—C22—H22 | 121.00 |
O10—N6—O11 | 124.30 (18) | C23—C22—H22 | 121.00 |
C18—N7—C19 | 125.40 (15) | C22—C23—H23 | 120.00 |
C19—N8—C20 | 125.59 (16) | C24—C23—H23 | 120.00 |
C19—N7—H7A | 118.0 (13) | C23—C24—H24 | 120.00 |
C18—N7—H7A | 116.4 (13) | C25—C24—H24 | 120.00 |
C20—N8—H8A | 115.6 (12) | C24—C25—H25 | 120.00 |
C19—N8—H8A | 118.6 (12) | C26—C25—H25 | 120.00 |
C21—N9—C29 | 111.79 (17) | C25—C26—H26 | 120.00 |
C27—N9—C29 | 111.68 (19) | C21—C26—H26 | 120.00 |
C21—N9—C27 | 113.65 (17) | C28—C27—H27B | 109.00 |
C27—N9—H9A | 103.2 (12) | N9—C27—H27A | 109.00 |
C21—N9—H9A | 107.2 (13) | N9—C27—H27B | 109.00 |
C29—N9—H9A | 108.8 (13) | C28—C27—H27A | 109.00 |
C31—N10—C37 | 112.19 (19) | H27A—C27—H27B | 108.00 |
C31—N10—C39 | 114.9 (2) | C27—C28—H28A | 110.00 |
C37—N10—C39 | 112.6 (2) | C27—C28—H28C | 110.00 |
C31—N10—H10A | 108.4 (13) | H28B—C28—H28C | 109.00 |
C37—N10—H10A | 103.6 (14) | H28A—C28—H28C | 109.00 |
C39—N10—H10A | 104.2 (14) | H28A—C28—H28B | 109.00 |
C2—C1—C6 | 123.47 (18) | C27—C28—H28B | 109.00 |
N1—C1—C6 | 121.74 (18) | N9—C29—H29B | 109.00 |
N1—C1—C2 | 114.60 (19) | C30—C29—H29B | 109.00 |
C1—C2—C3 | 118.2 (2) | H29A—C29—H29B | 108.00 |
C2—C3—C4 | 121.8 (2) | N9—C29—H29A | 109.00 |
N2—C3—C4 | 120.0 (2) | C30—C29—H29A | 109.00 |
N2—C3—C2 | 118.2 (2) | C29—C30—H30C | 109.00 |
C3—C4—C5 | 118.9 (2) | H30A—C30—H30B | 109.00 |
C4—C5—C6 | 122.5 (2) | C29—C30—H30B | 109.00 |
C5—C6—C7 | 120.33 (18) | H30A—C30—H30C | 109.00 |
C1—C6—C7 | 124.46 (16) | H30B—C30—H30C | 110.00 |
C1—C6—C5 | 115.15 (18) | C29—C30—H30A | 109.00 |
C6—C7—C8 | 120.21 (16) | N10—C31—C32 | 121.1 (2) |
C8—C7—C10 | 119.71 (17) | N10—C31—C36 | 117.4 (2) |
C6—C7—C10 | 120.06 (16) | C32—C31—C36 | 121.5 (2) |
O5—C8—N3 | 116.00 (17) | C31—C32—C33 | 117.8 (3) |
N3—C8—C7 | 117.37 (16) | C32—C33—C34 | 118.7 (3) |
O5—C8—C7 | 126.63 (19) | C33—C34—C35 | 122.4 (3) |
O7—C9—N3 | 122.01 (17) | C34—C35—C36 | 119.9 (3) |
N3—C9—N4 | 115.19 (17) | C31—C36—C35 | 119.7 (3) |
O7—C9—N4 | 122.80 (17) | N10—C37—C38 | 111.4 (2) |
O6—C10—C7 | 125.34 (18) | N10—C39—C40 | 111.0 (3) |
N4—C10—C7 | 116.81 (16) | C31—C32—H32 | 121.00 |
O6—C10—N4 | 117.84 (17) | C33—C32—H32 | 121.00 |
C1—C2—H2 | 121.00 | C32—C33—H33 | 121.00 |
C3—C2—H2 | 121.00 | C34—C33—H33 | 121.00 |
C5—C4—H4 | 121.00 | C33—C34—H34 | 119.00 |
C3—C4—H4 | 121.00 | C35—C34—H34 | 119.00 |
C4—C5—H5 | 119.00 | C34—C35—H35 | 120.00 |
C6—C5—H5 | 119.00 | C36—C35—H35 | 120.00 |
C12—C11—C16 | 121.7 (2) | C31—C36—H36 | 120.00 |
N5—C11—C12 | 118.6 (2) | C35—C36—H36 | 120.00 |
N5—C11—C16 | 119.67 (19) | N10—C37—H37A | 109.00 |
C11—C12—C13 | 117.8 (2) | N10—C37—H37B | 109.00 |
N6—C13—C14 | 121.80 (17) | C38—C37—H37A | 109.00 |
C12—C13—C14 | 123.33 (17) | C38—C37—H37B | 109.00 |
N6—C13—C12 | 114.66 (18) | H37A—C37—H37B | 108.00 |
C13—C14—C17 | 124.02 (16) | C37—C38—H38A | 110.00 |
C13—C14—C15 | 115.49 (18) | C37—C38—H38B | 110.00 |
C15—C14—C17 | 120.40 (18) | C37—C38—H38C | 109.00 |
C14—C15—C16 | 122.6 (2) | H38A—C38—H38B | 109.00 |
C11—C16—C15 | 119.02 (19) | H38A—C38—H38C | 109.00 |
C18—C17—C20 | 120.48 (17) | H38B—C38—H38C | 109.00 |
C14—C17—C18 | 119.84 (16) | N10—C39—H39A | 109.00 |
C14—C17—C20 | 119.66 (16) | N10—C39—H39B | 109.00 |
O12—C18—N7 | 117.00 (16) | C40—C39—H39A | 110.00 |
N7—C18—C17 | 116.90 (16) | C40—C39—H39B | 109.00 |
O12—C18—C17 | 126.09 (17) | H39A—C39—H39B | 108.00 |
N7—C19—N8 | 115.13 (16) | C39—C40—H40A | 109.00 |
O13—C19—N8 | 122.97 (17) | C39—C40—H40B | 109.00 |
O13—C19—N7 | 121.90 (16) | C39—C40—H40C | 109.00 |
N8—C20—C17 | 116.36 (15) | H40A—C40—H40B | 110.00 |
O14—C20—C17 | 125.60 (19) | H40A—C40—H40C | 109.00 |
O14—C20—N8 | 118.01 (17) | H40B—C40—H40C | 109.00 |
O1—N1—C1—C2 | 130.8 (2) | C2—C3—C4—C5 | −1.8 (3) |
O2—N1—C1—C2 | −45.6 (3) | C3—C4—C5—C6 | 2.0 (3) |
O1—N1—C1—C6 | −44.4 (3) | C4—C5—C6—C7 | −177.22 (19) |
O2—N1—C1—C6 | 139.1 (2) | C4—C5—C6—C1 | 0.0 (3) |
O3—N2—C3—C4 | −174.1 (2) | C1—C6—C7—C8 | 141.06 (19) |
O3—N2—C3—C2 | 5.3 (3) | C5—C6—C7—C8 | −42.0 (3) |
O4—N2—C3—C2 | −173.9 (2) | C1—C6—C7—C10 | −40.6 (3) |
O4—N2—C3—C4 | 6.8 (3) | C5—C6—C7—C10 | 136.35 (19) |
C8—N3—C9—O7 | −178.71 (18) | C10—C7—C8—N3 | 1.3 (3) |
C8—N3—C9—N4 | 1.6 (3) | C10—C7—C8—O5 | −178.59 (19) |
C9—N3—C8—C7 | −2.3 (3) | C8—C7—C10—O6 | 179.07 (18) |
C9—N3—C8—O5 | 177.59 (18) | C8—C7—C10—N4 | 0.1 (3) |
C9—N4—C10—C7 | −0.8 (3) | C6—C7—C8—N3 | 179.61 (17) |
C10—N4—C9—O7 | −179.67 (17) | C6—C7—C8—O5 | −0.2 (3) |
C10—N4—C9—N3 | 0.0 (3) | C6—C7—C10—N4 | −178.22 (16) |
C9—N4—C10—O6 | −179.84 (18) | C6—C7—C10—O6 | 0.7 (3) |
O8—N5—C11—C12 | −171.88 (19) | N5—C11—C12—C13 | 175.26 (17) |
O9—N5—C11—C12 | 7.8 (3) | N5—C11—C16—C15 | −177.10 (17) |
O9—N5—C11—C16 | −175.5 (2) | C16—C11—C12—C13 | −1.3 (3) |
O8—N5—C11—C16 | 4.8 (3) | C12—C11—C16—C15 | −0.6 (3) |
O10—N6—C13—C12 | 132.40 (19) | C11—C12—C13—C14 | 3.0 (3) |
O10—N6—C13—C14 | −42.5 (3) | C11—C12—C13—N6 | −171.77 (17) |
O11—N6—C13—C14 | 141.2 (2) | C12—C13—C14—C17 | 173.92 (18) |
O11—N6—C13—C12 | −43.9 (3) | C12—C13—C14—C15 | −2.7 (3) |
C19—N7—C18—C17 | −4.2 (3) | N6—C13—C14—C15 | 171.77 (17) |
C19—N7—C18—O12 | 176.98 (17) | N6—C13—C14—C17 | −11.6 (3) |
C18—N7—C19—N8 | 1.7 (3) | C13—C14—C15—C16 | 0.7 (3) |
C18—N7—C19—O13 | −178.88 (17) | C15—C14—C17—C18 | 133.29 (19) |
C20—N8—C19—O13 | −177.98 (18) | C13—C14—C17—C20 | 138.12 (19) |
C19—N8—C20—C17 | −1.7 (3) | C17—C14—C15—C16 | −176.07 (17) |
C19—N8—C20—O14 | 180.00 (17) | C13—C14—C17—C18 | −43.1 (3) |
C20—N8—C19—N7 | 1.4 (3) | C15—C14—C17—C20 | −45.5 (3) |
C21—N9—C27—C28 | 56.7 (3) | C14—C15—C16—C11 | 0.9 (3) |
C29—N9—C27—C28 | −175.7 (2) | C14—C17—C20—O14 | −4.1 (3) |
C27—N9—C21—C22 | 52.3 (3) | C18—C17—C20—O14 | 177.14 (19) |
C27—N9—C29—C30 | 165.7 (2) | C20—C17—C18—O12 | −177.63 (18) |
C29—N9—C21—C22 | −75.2 (2) | C18—C17—C20—N8 | −1.0 (3) |
C27—N9—C21—C26 | −128.8 (2) | C14—C17—C20—N8 | 177.70 (16) |
C29—N9—C21—C26 | 103.7 (2) | C14—C17—C18—O12 | 3.7 (3) |
C21—N9—C29—C30 | −65.7 (3) | C20—C17—C18—N7 | 3.7 (3) |
C37—N10—C31—C36 | −97.4 (3) | C14—C17—C18—N7 | −175.01 (16) |
C39—N10—C37—C38 | −168.8 (2) | C26—C21—C22—C23 | 0.6 (3) |
C31—N10—C39—C40 | −57.8 (3) | N9—C21—C26—C25 | −178.91 (19) |
C31—N10—C37—C38 | 59.8 (3) | C22—C21—C26—C25 | 0.0 (3) |
C37—N10—C31—C32 | 79.7 (3) | N9—C21—C22—C23 | 179.5 (2) |
C39—N10—C31—C36 | 132.4 (3) | C21—C22—C23—C24 | −0.3 (4) |
C39—N10—C31—C32 | −50.6 (3) | C22—C23—C24—C25 | −0.6 (4) |
C37—N10—C39—C40 | 172.2 (2) | C23—C24—C25—C26 | 1.2 (4) |
N1—C1—C6—C5 | 172.57 (19) | C24—C25—C26—C21 | −0.9 (4) |
C2—C1—C6—C5 | −2.3 (3) | N10—C31—C32—C33 | −178.3 (3) |
N1—C1—C6—C7 | −10.4 (3) | C36—C31—C32—C33 | −1.3 (4) |
C6—C1—C2—C3 | 2.5 (3) | N10—C31—C36—C35 | 177.9 (3) |
C2—C1—C6—C7 | 174.82 (19) | C32—C31—C36—C35 | 0.8 (4) |
N1—C1—C2—C3 | −172.69 (19) | C31—C32—C33—C34 | 1.6 (5) |
C1—C2—C3—N2 | −179.72 (19) | C32—C33—C34—C35 | −1.3 (6) |
C1—C2—C3—C4 | −0.3 (3) | C33—C34—C35—C36 | 0.8 (6) |
N2—C3—C4—C5 | 177.6 (2) | C34—C35—C36—C31 | −0.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O7i | 0.89 (2) | 2.00 (2) | 2.878 (2) | 172 (2) |
N4—H4A···O14ii | 0.87 (2) | 1.93 (2) | 2.802 (2) | 172 (2) |
N7—H7A···O13iii | 0.88 (2) | 2.06 (2) | 2.931 (2) | 175 (2) |
N8—H8A···O6iv | 0.89 (2) | 1.98 (2) | 2.852 (2) | 164 (2) |
N9—H9A···O12 | 0.90 (2) | 1.83 (2) | 2.726 (2) | 176 (1) |
N10—H10A···O5v | 0.92 (2) | 1.69 (2) | 2.598 (3) | 166 (2) |
C12—H12···O4vi | 0.93 | 2.52 | 3.451 (3) | 174 |
C26—H26···O12 | 0.93 | 2.59 | 3.272 (3) | 131 |
C26—H26···O13iii | 0.93 | 2.56 | 3.281 (3) | 135 |
C29—H29B···O11 | 0.97 | 2.57 | 3.215 (3) | 124 |
C38—H38A···O7i | 0.96 | 2.52 | 3.484 (3) | 177 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H16N+·C10H5N4O7− |
Mr | 443.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.7260 (2), 14.2930 (3), 18.1080 (5) |
α, β, γ (°) | 106.712 (1), 96.490 (1), 97.667 (1) |
V (Å3) | 2116.27 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.944, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36083, 7482, 5563 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.122, 1.02 |
No. of reflections | 7482 |
No. of parameters | 601 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.21 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O7i | 0.885 (18) | 2.000 (18) | 2.878 (2) | 171.8 (16) |
N4—H4A···O14ii | 0.874 (18) | 1.933 (17) | 2.802 (2) | 172 (2) |
N7—H7A···O13iii | 0.877 (16) | 2.056 (16) | 2.931 (2) | 175.1 (19) |
N8—H8A···O6iv | 0.892 (19) | 1.983 (18) | 2.852 (2) | 164.4 (18) |
N9—H9A···O12 | 0.902 (18) | 1.825 (18) | 2.726 (2) | 176.2 (14) |
N10—H10A···O5v | 0.92 (2) | 1.69 (2) | 2.598 (3) | 165.6 (19) |
C12—H12···O4vi | 0.93 | 2.52 | 3.451 (3) | 174 |
C26—H26···O12 | 0.93 | 2.59 | 3.272 (3) | 131 |
C26—H26···O13iii | 0.93 | 2.56 | 3.281 (3) | 135 |
C29—H29B···O11 | 0.97 | 2.57 | 3.215 (3) | 124 |
C38—H38A···O7i | 0.96 | 2.52 | 3.484 (3) | 177 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) x, y−1, z. |
Acknowledgements
The authors are thankful to the SAIF, IIT Madras, for the data collection.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The methylene group of barbituric acid [a pyrimidine derivative] is flanked on both sides by the electron-withdrawing carbonyl groups which makes the hydrogen atoms highly acidic. These acidic H atoms have been targeted by our group in the preparation of a number of extraordinarily stable barbiturates (Kalaivani & Malarvizhi, 2009; Buvaneswari & Kalaivani, 2011a; Kalaivani et al., 2012; Babykala & Kalaivani, 2012). We have reported on the crystal structure of a barbiturate related to the title molecular salt but derived from 1-chloro-2,4,6-trinitrobenzene (TNCB) and barbituric acid in the presence of N,N-diethylaniline (I) (Buvaneswari & Kalaivani, 2011b). Herein we report on the crystal structure of the new title molecular salt obtained from 1-chloro-2,4-dinitrobenzene (DNCB) and barbituric acid in the presence of N,N-diethylaniline, (II).
Unlike the asymmetric unit of the related reported barbiturate (I), which comprises of only one anion and cation moieties, the asymmetric unit of the barbiturate of the title compound (II) is composed of two cations and two anions (Fig. 1). Contrary to the barbiturate of TNCB (I), which crystallized in the monoclinic space group P21/c, the title compound (II) crystallized in the triclinic space group P1.
In the crystal of (II), the anions are linked via N—H···O hydrogen bonds (Table 1 and Fig. 2), forming chains along direction [1 0 -1]. This linkage and the R22(8) ring motifs formed between inversion-related barbiturate residues contributes considerably to the extraordinary stability of the title molecular salt. The cations are linked to the chains via N-H···O hydrogen bonds (Table 1 and Fig. 2). There are C-H···O interactions present (Table 1) but no π-π stacking interactions between the N,N-diethylaniline and 2,4-dinitrophenyl ring moieties.
As barbiturates are employed in the treatment of neurological disorders (Hueso et al., 2003; Kalaivani et al., 2008; Tripathi, 2009; Kalaivani & Buvaneswari, 2010), the non-bonding interactions of the present investigation may help to understand the mechanistic aspects of the physiological action of barbiturates.