organic compounds
R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate
of 2-amino-4-methylpyridin-1-ium (2aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Physics, Loyola College, Chennai-34, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
The title molecular salt, C6H9N2+·C4H5O6−·H2O, crystallized with two 2-amino-4-methylpyridin-1-ium cations, two L-(+)-tartaric acid monoanions [systematic name: (2R,3R)-3-carboxy-2,3-dihydroxypropanoate] and two water molecules in the In the crystal, the cations, anions and water molecules are linked via a number of O—H⋯O and N—H⋯O hydrogen bonds, and a C—H⋯O hydrogen bond, forming a three-dimensional structure
CCDC reference: 1019274
1. Related literature
For the biological activity of pyridinium derivatives, see: Judge & Bever (2006); Schwid et al. (1997); Strupp et al. (2004). For the of a related molecular salt involving the 2-amino-4-methylpyridin-1-ium cation, see: Hemamalini & Fun (2010).
2. Experimental
2.1. Crystal data
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2.3. 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 1019274
10.1107/S160053681401842X/su2748sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681401842X/su2748Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681401842X/su2748Isup3.cml
The title compound was prepared by mixing an equimolar ratio of 4-methylpyridin-2-amine (Aldrich) with L-(+)-tartaric acid (Spectrochem). When the tartaric acid was added to a
of 4-methylpyridin-2-amine in acetone a pale pink coloured precipitate was formed. The precipitate was collected and allowed to dry and powdered. Suitable crystals of the title salt were prepared by slow evaporation of a solution of the powder in methanol at room temperature.The water, NH and OH H atoms were located from difference Fourier maps and freely refined. The C-bound H atoms were positioned geometrically and treated as riding atoms: C—H = 0.93–0.98 Å Uiso(H)= 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details). |
C6H9N2+·C4H5O6−·H2O | Z = 2 |
Mr = 276.25 | F(000) = 292 |
Triclinic, P1 | Dx = 1.422 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.176 (3) Å | Cell parameters from 8251 reflections |
b = 9.9359 (18) Å | θ = 2.3–32.6° |
c = 10.716 (2) Å | µ = 0.12 mm−1 |
α = 117.528 (5)° | T = 293 K |
β = 104.792 (7)° | Block, colourless |
γ = 91.701 (7)° | 0.24 × 0.22 × 0.20 mm |
V = 645.3 (3) Å3 |
Bruker APEXII CCD diffractometer | 4999 independent reflections |
Radiation source: fine-focus sealed tube | 4769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.971, Tmax = 0.976 | k = −12→12 |
10211 measured reflections | l = −13→13 |
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)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.1123P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
4999 reflections | Δρmax = 0.27 e Å−3 |
410 parameters | Δρmin = −0.17 e Å−3 |
3 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.055 (5) |
C6H9N2+·C4H5O6−·H2O | γ = 91.701 (7)° |
Mr = 276.25 | V = 645.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.176 (3) Å | Mo Kα radiation |
b = 9.9359 (18) Å | µ = 0.12 mm−1 |
c = 10.716 (2) Å | T = 293 K |
α = 117.528 (5)° | 0.24 × 0.22 × 0.20 mm |
β = 104.792 (7)° |
Bruker APEXII CCD diffractometer | 4999 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4769 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.976 | Rint = 0.022 |
10211 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 3 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.27 e Å−3 |
4999 reflections | Δρmin = −0.17 e Å−3 |
410 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 | 0.74569 (19) | 0.24776 (17) | 0.32479 (15) | 0.0425 (4) | |
O2 | 0.8383 (2) | 0.48800 (17) | 0.51261 (16) | 0.0434 (4) | |
O3 | 0.4999 (2) | 0.52134 (16) | 0.54862 (17) | 0.0421 (5) | |
O4 | 0.5543 (2) | 0.25906 (18) | 0.58628 (16) | 0.0402 (4) | |
O5 | 0.09901 (19) | 0.22642 (16) | 0.33245 (15) | 0.0385 (4) | |
O6 | 0.1808 (2) | 0.2985 (2) | 0.57363 (17) | 0.0469 (5) | |
O7 | 0.73206 (18) | 0.84899 (15) | 0.69807 (16) | 0.0366 (4) | |
O8 | 0.8096 (2) | 1.08215 (17) | 0.89449 (17) | 0.0443 (4) | |
O9 | 1.1844 (2) | 1.09612 (17) | 0.92901 (15) | 0.0408 (4) | |
O10 | 1.0198 (2) | 1.08903 (18) | 0.65507 (18) | 0.0440 (5) | |
O11 | 1.3678 (3) | 1.0395 (2) | 0.6194 (3) | 0.0676 (8) | |
O12 | 1.38559 (17) | 0.86225 (14) | 0.69019 (15) | 0.0340 (4) | |
C13 | 0.7165 (2) | 0.3699 (2) | 0.42355 (19) | 0.0302 (5) | |
C14 | 0.5072 (3) | 0.3760 (2) | 0.4327 (2) | 0.0299 (5) | |
C15 | 0.4308 (2) | 0.2468 (2) | 0.4546 (2) | 0.0295 (5) | |
C16 | 0.2212 (2) | 0.25924 (19) | 0.4604 (2) | 0.0298 (5) | |
C17 | 0.8533 (2) | 0.9703 (2) | 0.80181 (19) | 0.0286 (5) | |
C18 | 1.0658 (2) | 0.9648 (2) | 0.80165 (19) | 0.0275 (5) | |
C19 | 1.0873 (2) | 0.95937 (19) | 0.66195 (19) | 0.0290 (5) | |
C20 | 1.2990 (2) | 0.9559 (2) | 0.65682 (19) | 0.0300 (5) | |
N1 | 0.0123 (3) | 0.3863 (2) | −0.09469 (18) | 0.0368 (5) | |
N2 | 0.0764 (3) | 0.3843 (2) | 0.1268 (2) | 0.0444 (6) | |
C1 | 0.0410 (3) | 0.4600 (2) | 0.0521 (2) | 0.0316 (5) | |
C2 | 0.0344 (3) | 0.6200 (2) | 0.1196 (2) | 0.0355 (5) | |
C3 | 0.0001 (3) | 0.6933 (2) | 0.0375 (2) | 0.0391 (6) | |
C4 | −0.0325 (3) | 0.6082 (3) | −0.1162 (2) | 0.0417 (7) | |
C5 | −0.0249 (3) | 0.4564 (2) | −0.1787 (2) | 0.0397 (6) | |
C6 | −0.0012 (5) | 0.8623 (3) | 0.1096 (3) | 0.0639 (9) | |
N3 | 0.4969 (3) | 0.4655 (2) | 0.8719 (2) | 0.0450 (6) | |
N4 | 0.4515 (3) | 0.6816 (3) | 0.8476 (3) | 0.0535 (8) | |
O1W | 1.1106 (3) | 0.58916 (19) | 0.42444 (17) | 0.0448 (5) | |
C7 | 0.5351 (4) | 0.3913 (3) | 0.9520 (3) | 0.0528 (8) | |
C8 | 0.5627 (4) | 0.4668 (3) | 1.0974 (3) | 0.0529 (8) | |
C9 | 0.5523 (3) | 0.6239 (3) | 1.1678 (2) | 0.0499 (8) | |
C10 | 0.5161 (3) | 0.6983 (3) | 1.0861 (2) | 0.0426 (6) | |
C11 | 0.4877 (3) | 0.6164 (2) | 0.9329 (2) | 0.0367 (6) | |
C12 | 0.5813 (6) | 0.7111 (5) | 1.3315 (3) | 0.0825 (13) | |
O2W | 1.5440 (2) | 1.04131 (19) | 1.03282 (18) | 0.0444 (5) | |
H3 | 0.613 (5) | 0.565 (4) | 0.575 (4) | 0.067 (9)* | |
H4A | 0.513 (5) | 0.170 (4) | 0.582 (3) | 0.062 (8)* | |
H5A | −0.057 (6) | 0.230 (4) | 0.344 (4) | 0.098 (12)* | |
H14 | 0.42260 | 0.36470 | 0.33960 | 0.0360* | |
H15 | 0.43150 | 0.14750 | 0.37120 | 0.0350* | |
H7A | 0.582 (5) | 0.862 (4) | 0.698 (4) | 0.082 (10)* | |
H9 | 1.300 (4) | 1.068 (3) | 0.959 (3) | 0.055 (7)* | |
H10A | 1.091 (4) | 1.116 (3) | 0.618 (3) | 0.053 (7)* | |
H18 | 1.10350 | 0.87210 | 0.80480 | 0.0330* | |
H19 | 1.00390 | 0.86590 | 0.57650 | 0.0350* | |
H2 | 0.05370 | 0.67540 | 0.22070 | 0.0430* | |
H2NA | 0.085 (3) | 0.429 (3) | 0.217 (3) | 0.029 (5)* | |
H4 | −0.05890 | 0.65630 | −0.17380 | 0.0500* | |
H2NB | 0.071 (5) | 0.290 (4) | 0.081 (3) | 0.058 (8)* | |
H5 | −0.04540 | 0.39950 | −0.27990 | 0.0480* | |
H6A | 0.09330 | 0.91180 | 0.08800 | 0.0960* | |
H6B | 0.03140 | 0.90320 | 0.21460 | 0.0960* | |
H6C | −0.12900 | 0.88070 | 0.07290 | 0.0960* | |
H29 | 0.015 (4) | 0.299 (3) | −0.138 (3) | 0.047 (7)* | |
H3N | 0.481 (4) | 0.412 (3) | 0.781 (3) | 0.048 (7)* | |
H7 | 0.54230 | 0.28690 | 0.90550 | 0.0630* | |
H4NA | 0.441 (4) | 0.624 (3) | 0.754 (3) | 0.045 (7)* | |
H8 | 0.58890 | 0.41520 | 1.15170 | 0.0630* | |
H4NB | 0.452 (5) | 0.776 (4) | 0.890 (4) | 0.068 (10)* | |
H10 | 0.51030 | 0.80290 | 1.13180 | 0.0510* | |
H12A | 0.70470 | 0.69940 | 1.38340 | 0.1240* | |
H12B | 0.47770 | 0.67110 | 1.35330 | 0.1240* | |
H12C | 0.57980 | 0.81830 | 1.36210 | 0.1240* | |
H1WA | 1.033 (4) | 0.554 (3) | 0.457 (3) | 0.052 (7)* | |
H1WB | 1.211 (5) | 0.620 (3) | 0.487 (3) | 0.055 (8)* | |
H2WA | 1.617 (5) | 1.059 (4) | 0.992 (3) | 0.062 (9)* | |
H2WB | 1.591 (4) | 1.099 (3) | 1.125 (4) | 0.051 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0253 (6) | 0.0529 (9) | 0.0359 (7) | 0.0069 (6) | 0.0113 (5) | 0.0098 (7) |
O2 | 0.0303 (7) | 0.0451 (8) | 0.0468 (8) | −0.0004 (6) | 0.0125 (6) | 0.0160 (7) |
O3 | 0.0397 (8) | 0.0312 (7) | 0.0588 (9) | 0.0085 (6) | 0.0267 (7) | 0.0185 (7) |
O4 | 0.0343 (7) | 0.0467 (8) | 0.0487 (8) | 0.0063 (6) | 0.0085 (6) | 0.0326 (7) |
O5 | 0.0257 (6) | 0.0419 (7) | 0.0344 (7) | 0.0021 (5) | 0.0100 (5) | 0.0076 (6) |
O6 | 0.0457 (8) | 0.0691 (10) | 0.0530 (9) | 0.0287 (8) | 0.0309 (7) | 0.0421 (8) |
O7 | 0.0240 (6) | 0.0291 (6) | 0.0471 (8) | 0.0044 (5) | 0.0135 (5) | 0.0095 (6) |
O8 | 0.0300 (7) | 0.0367 (7) | 0.0509 (8) | 0.0049 (6) | 0.0193 (6) | 0.0056 (6) |
O9 | 0.0262 (6) | 0.0410 (7) | 0.0380 (7) | 0.0055 (6) | 0.0055 (5) | 0.0076 (6) |
O10 | 0.0455 (8) | 0.0532 (9) | 0.0648 (9) | 0.0284 (7) | 0.0330 (8) | 0.0444 (8) |
O11 | 0.0513 (9) | 0.0784 (12) | 0.1307 (18) | 0.0294 (9) | 0.0552 (11) | 0.0819 (13) |
O12 | 0.0245 (6) | 0.0340 (7) | 0.0484 (7) | 0.0084 (5) | 0.0153 (5) | 0.0215 (6) |
C13 | 0.0263 (8) | 0.0413 (10) | 0.0292 (8) | 0.0072 (8) | 0.0106 (7) | 0.0209 (8) |
C14 | 0.0258 (8) | 0.0355 (9) | 0.0334 (9) | 0.0074 (7) | 0.0111 (7) | 0.0196 (7) |
C15 | 0.0262 (8) | 0.0291 (8) | 0.0336 (9) | 0.0057 (7) | 0.0115 (7) | 0.0142 (7) |
C16 | 0.0286 (9) | 0.0254 (8) | 0.0402 (9) | 0.0063 (7) | 0.0156 (7) | 0.0170 (7) |
C17 | 0.0255 (8) | 0.0306 (9) | 0.0342 (9) | 0.0070 (7) | 0.0123 (7) | 0.0176 (7) |
C18 | 0.0233 (8) | 0.0249 (8) | 0.0357 (9) | 0.0063 (6) | 0.0106 (7) | 0.0150 (7) |
C19 | 0.0242 (8) | 0.0291 (9) | 0.0362 (9) | 0.0073 (7) | 0.0117 (7) | 0.0164 (8) |
C20 | 0.0286 (8) | 0.0274 (8) | 0.0360 (9) | 0.0053 (7) | 0.0153 (7) | 0.0141 (7) |
N1 | 0.0436 (9) | 0.0281 (8) | 0.0353 (8) | 0.0098 (7) | 0.0149 (7) | 0.0109 (7) |
N2 | 0.0646 (12) | 0.0312 (9) | 0.0364 (10) | 0.0133 (8) | 0.0164 (8) | 0.0149 (8) |
C1 | 0.0290 (8) | 0.0311 (9) | 0.0334 (9) | 0.0063 (7) | 0.0106 (7) | 0.0140 (8) |
C2 | 0.0381 (10) | 0.0292 (9) | 0.0329 (9) | 0.0061 (7) | 0.0124 (8) | 0.0093 (8) |
C3 | 0.0349 (10) | 0.0307 (10) | 0.0507 (11) | 0.0032 (8) | 0.0128 (9) | 0.0193 (9) |
C4 | 0.0407 (11) | 0.0459 (12) | 0.0473 (11) | 0.0082 (9) | 0.0135 (9) | 0.0295 (10) |
C5 | 0.0385 (10) | 0.0480 (12) | 0.0335 (9) | 0.0073 (8) | 0.0123 (8) | 0.0198 (9) |
C6 | 0.0813 (19) | 0.0347 (12) | 0.0725 (17) | 0.0119 (12) | 0.0208 (15) | 0.0248 (12) |
N3 | 0.0541 (11) | 0.0444 (10) | 0.0342 (9) | 0.0062 (8) | 0.0122 (8) | 0.0179 (8) |
N4 | 0.0698 (14) | 0.0596 (13) | 0.0480 (12) | 0.0180 (11) | 0.0234 (10) | 0.0365 (11) |
O1W | 0.0442 (8) | 0.0447 (8) | 0.0366 (8) | −0.0045 (7) | 0.0102 (7) | 0.0143 (7) |
C7 | 0.0550 (13) | 0.0454 (12) | 0.0626 (15) | 0.0048 (10) | 0.0142 (11) | 0.0320 (12) |
C8 | 0.0500 (13) | 0.0651 (15) | 0.0577 (14) | 0.0048 (11) | 0.0122 (11) | 0.0435 (13) |
C9 | 0.0369 (11) | 0.0773 (17) | 0.0395 (11) | 0.0048 (11) | 0.0085 (9) | 0.0334 (12) |
C10 | 0.0403 (11) | 0.0472 (12) | 0.0404 (10) | 0.0109 (9) | 0.0156 (9) | 0.0194 (9) |
C11 | 0.0319 (9) | 0.0461 (11) | 0.0376 (10) | 0.0063 (8) | 0.0126 (7) | 0.0238 (9) |
C12 | 0.092 (2) | 0.108 (3) | 0.0447 (14) | 0.019 (2) | 0.0205 (15) | 0.0349 (16) |
O2W | 0.0345 (7) | 0.0524 (9) | 0.0328 (8) | 0.0026 (6) | 0.0055 (6) | 0.0125 (7) |
O1—C13 | 1.256 (2) | C2—C3 | 1.363 (3) |
O2—C13 | 1.237 (3) | N2—H2NA | 0.84 (3) |
O3—C14 | 1.418 (3) | N2—H2NB | 0.83 (4) |
O4—C15 | 1.410 (2) | C3—C4 | 1.410 (3) |
O5—C16 | 1.308 (2) | C3—C6 | 1.491 (4) |
O6—C16 | 1.207 (2) | C4—C5 | 1.348 (4) |
O3—H3 | 0.82 (4) | C2—H2 | 0.9300 |
O4—H4A | 0.90 (4) | N3—C11 | 1.342 (3) |
O5—H5A | 1.16 (4) | N3—C7 | 1.354 (4) |
O7—C17 | 1.285 (2) | N4—C11 | 1.326 (4) |
O8—C17 | 1.216 (3) | C4—H4 | 0.9300 |
O9—C18 | 1.409 (2) | C5—H5 | 0.9300 |
O10—C19 | 1.417 (3) | C6—H6A | 0.9600 |
O11—C20 | 1.216 (3) | C6—H6B | 0.9600 |
O12—C20 | 1.268 (3) | C6—H6C | 0.9600 |
C13—C14 | 1.531 (3) | N3—H3N | 0.84 (3) |
C14—C15 | 1.519 (3) | N4—H4NB | 0.83 (4) |
C15—C16 | 1.527 (2) | N4—H4NA | 0.88 (3) |
O7—H7A | 1.09 (4) | C7—C8 | 1.335 (4) |
O9—H9 | 0.91 (3) | C8—C9 | 1.399 (4) |
O10—H10A | 0.83 (3) | C9—C10 | 1.369 (4) |
C14—H14 | 0.9800 | C9—C12 | 1.506 (3) |
C15—H15 | 0.9800 | C10—C11 | 1.408 (3) |
C17—C18 | 1.528 (2) | O1W—H1WB | 0.78 (3) |
C18—C19 | 1.520 (3) | O1W—H1WA | 0.87 (3) |
C19—C20 | 1.535 (2) | C7—H7 | 0.9300 |
N1—C5 | 1.355 (3) | C8—H8 | 0.9300 |
N1—C1 | 1.347 (3) | C10—H10 | 0.9300 |
N2—C1 | 1.317 (3) | C12—H12C | 0.9600 |
C18—H18 | 0.9800 | C12—H12A | 0.9600 |
C19—H19 | 0.9800 | C12—H12B | 0.9600 |
C1—C2 | 1.418 (3) | O2W—H2WA | 0.82 (4) |
N1—H29 | 0.78 (3) | O2W—H2WB | 0.84 (4) |
C14—O3—H3 | 100 (3) | C1—N2—H2NB | 119 (2) |
C15—O4—H4A | 103.0 (19) | C1—C2—C3 | 120.58 (17) |
C16—O5—H5A | 108.0 (18) | H2NA—N2—H2NB | 121 (3) |
O1—C13—C14 | 116.99 (16) | C2—C3—C4 | 119.4 (2) |
O1—C13—O2 | 126.88 (16) | C4—C3—C6 | 120.2 (2) |
O2—C13—C14 | 116.10 (17) | C2—C3—C6 | 120.37 (19) |
O3—C14—C13 | 109.65 (16) | C3—C4—C5 | 119.3 (2) |
O3—C14—C15 | 110.52 (16) | N1—C5—C4 | 120.27 (18) |
C13—C14—C15 | 111.91 (17) | C1—C2—H2 | 120.00 |
C14—C15—C16 | 108.80 (17) | C3—C2—H2 | 120.00 |
O4—C15—C14 | 108.89 (16) | C7—N3—C11 | 122.6 (2) |
O4—C15—C16 | 111.36 (15) | C5—C4—H4 | 120.00 |
O5—C16—O6 | 126.04 (16) | C3—C4—H4 | 120.00 |
O5—C16—C15 | 112.27 (15) | N1—C5—H5 | 120.00 |
O6—C16—C15 | 121.67 (16) | C4—C5—H5 | 120.00 |
C17—O7—H7A | 111 (2) | C3—C6—H6B | 109.00 |
C18—O9—H9 | 107.2 (19) | C3—C6—H6C | 109.00 |
C19—O10—H10A | 106 (2) | C3—C6—H6A | 109.00 |
O3—C14—H14 | 108.00 | H6A—C6—H6C | 110.00 |
C13—C14—H14 | 108.00 | H6B—C6—H6C | 109.00 |
C15—C14—H14 | 108.00 | H6A—C6—H6B | 109.00 |
C16—C15—H15 | 109.00 | C11—N3—H3N | 121 (2) |
O4—C15—H15 | 109.00 | C7—N3—H3N | 116 (2) |
C14—C15—H15 | 109.00 | C11—N4—H4NA | 118 (2) |
O7—C17—C18 | 114.13 (16) | H4NA—N4—H4NB | 126 (3) |
O7—C17—O8 | 125.05 (16) | C11—N4—H4NB | 116 (3) |
O8—C17—C18 | 120.83 (17) | N3—C7—C8 | 120.5 (3) |
O9—C18—C17 | 108.17 (14) | C7—C8—C9 | 119.9 (3) |
O9—C18—C19 | 111.32 (16) | C8—C9—C12 | 120.8 (3) |
C17—C18—C19 | 109.84 (14) | C10—C9—C12 | 120.1 (3) |
C18—C19—C20 | 112.12 (14) | C8—C9—C10 | 119.2 (2) |
O10—C19—C18 | 108.04 (15) | C9—C10—C11 | 120.0 (2) |
O10—C19—C20 | 111.07 (16) | N3—C11—C10 | 117.8 (2) |
O11—C20—O12 | 125.81 (18) | N4—C11—C10 | 122.9 (2) |
O11—C20—C19 | 118.3 (2) | N3—C11—N4 | 119.2 (2) |
O12—C20—C19 | 115.93 (17) | H1WA—O1W—H1WB | 105 (3) |
C1—N1—C5 | 123.5 (2) | N3—C7—H7 | 120.00 |
C17—C18—H18 | 109.00 | C8—C7—H7 | 120.00 |
C19—C18—H18 | 109.00 | C9—C8—H8 | 120.00 |
O9—C18—H18 | 109.00 | C7—C8—H8 | 120.00 |
C18—C19—H19 | 109.00 | C9—C10—H10 | 120.00 |
C20—C19—H19 | 108.00 | C11—C10—H10 | 120.00 |
O10—C19—H19 | 109.00 | C9—C12—H12B | 109.00 |
N1—C1—N2 | 120.2 (2) | C9—C12—H12C | 109.00 |
N1—C1—C2 | 116.89 (19) | C9—C12—H12A | 109.00 |
N2—C1—C2 | 122.93 (18) | H12A—C12—H12C | 110.00 |
C5—N1—H29 | 115 (2) | H12B—C12—H12C | 109.00 |
C1—N1—H29 | 122 (2) | H12A—C12—H12B | 109.00 |
C1—N2—H2NA | 120 (2) | H2WA—O2W—H2WB | 109 (3) |
O1—C13—C14—O3 | −179.57 (18) | C18—C19—C20—O11 | −135.1 (2) |
O1—C13—C14—C15 | 57.4 (2) | C18—C19—C20—O12 | 46.2 (2) |
O2—C13—C14—O3 | −1.2 (3) | C5—N1—C1—N2 | 180.0 (2) |
O2—C13—C14—C15 | −124.3 (2) | C5—N1—C1—C2 | −1.1 (3) |
O3—C14—C15—O4 | −63.3 (2) | C1—N1—C5—C4 | 0.9 (4) |
O3—C14—C15—C16 | 58.3 (2) | N2—C1—C2—C3 | 179.0 (2) |
C13—C14—C15—O4 | 59.26 (19) | N1—C1—C2—C3 | 0.1 (3) |
C13—C14—C15—C16 | −179.20 (14) | C1—C2—C3—C4 | 1.2 (3) |
O4—C15—C16—O5 | −170.89 (18) | C1—C2—C3—C6 | −178.3 (2) |
O4—C15—C16—O6 | 10.5 (3) | C6—C3—C4—C5 | 178.0 (2) |
C14—C15—C16—O5 | 69.1 (2) | C2—C3—C4—C5 | −1.4 (3) |
C14—C15—C16—O6 | −109.5 (2) | C3—C4—C5—N1 | 0.5 (3) |
O7—C17—C18—O9 | −173.74 (17) | C11—N3—C7—C8 | 1.0 (4) |
O7—C17—C18—C19 | 64.6 (2) | C7—N3—C11—N4 | 179.3 (2) |
O8—C17—C18—O9 | 6.1 (3) | C7—N3—C11—C10 | −1.1 (4) |
O8—C17—C18—C19 | −115.6 (2) | N3—C7—C8—C9 | −0.1 (4) |
O9—C18—C19—O10 | −63.25 (18) | C7—C8—C9—C12 | 179.5 (3) |
O9—C18—C19—C20 | 59.5 (2) | C7—C8—C9—C10 | −0.8 (4) |
C17—C18—C19—O10 | 56.5 (2) | C8—C9—C10—C11 | 0.7 (3) |
C17—C18—C19—C20 | 179.23 (17) | C12—C9—C10—C11 | −179.6 (3) |
O10—C19—C20—O11 | −14.1 (3) | C9—C10—C11—N4 | 179.8 (2) |
O10—C19—C20—O12 | 167.13 (16) | C9—C10—C11—N3 | 0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2 | 0.87 (3) | 1.86 (3) | 2.725 (3) | 172 (3) |
O1W—H1WB···O3i | 0.78 (3) | 2.39 (4) | 3.012 (3) | 137 (3) |
O1W—H1WB···O12 | 0.78 (3) | 2.39 (3) | 3.006 (3) | 137 (3) |
O3—H3···O2 | 0.82 (4) | 1.95 (4) | 2.562 (2) | 131 (4) |
O3—H3···O7 | 0.82 (4) | 2.51 (4) | 3.072 (3) | 127 (3) |
N2—H2NA···O1Wii | 0.84 (3) | 2.00 (3) | 2.819 (3) | 164 (3) |
N3—H3N···O4 | 0.84 (3) | 2.15 (3) | 2.939 (3) | 157 (3) |
N3—H3N···O6 | 0.84 (3) | 2.44 (3) | 3.047 (3) | 130 (3) |
N2—H2NB···O8iii | 0.83 (4) | 2.41 (3) | 3.032 (3) | 132 (3) |
N2—H2NB···O9iii | 0.83 (4) | 2.21 (4) | 2.942 (3) | 147 (3) |
O4—H4A···O11iv | 0.90 (4) | 1.88 (4) | 2.732 (3) | 156 (3) |
O2W—H2WA···O8i | 0.82 (4) | 2.00 (4) | 2.819 (3) | 173 (4) |
O5—H5A···O1ii | 1.16 (4) | 1.41 (4) | 2.534 (2) | 163 (4) |
N4—H4NA···O3 | 0.88 (3) | 2.12 (3) | 2.968 (3) | 163 (3) |
O7—H7A···O12ii | 1.09 (4) | 1.39 (4) | 2.476 (2) | 174 (4) |
N4—H4NB···O2Wii | 0.83 (4) | 2.32 (4) | 3.128 (4) | 164 (3) |
N4—H4NB···O12ii | 0.83 (4) | 2.60 (4) | 2.955 (4) | 108 (3) |
O9—H9···O2W | 0.91 (3) | 1.81 (3) | 2.715 (3) | 172 (3) |
O10—H10A···O6v | 0.83 (3) | 2.19 (3) | 2.912 (3) | 145 (3) |
O10—H10A···O11 | 0.83 (3) | 2.15 (3) | 2.648 (3) | 119 (3) |
N1—H29···O10iii | 0.78 (3) | 2.24 (3) | 2.946 (3) | 151 (3) |
C5—H5···O6vi | 0.93 | 2.46 | 3.158 (3) | 132 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x−1, y−1, z−1; (iv) x−1, y−1, z; (v) x+1, y+1, z; (vi) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2 | 0.87 (3) | 1.86 (3) | 2.725 (3) | 172 (3) |
O1W—H1WB···O3i | 0.78 (3) | 2.39 (4) | 3.012 (3) | 137 (3) |
O1W—H1WB···O12 | 0.78 (3) | 2.39 (3) | 3.006 (3) | 137 (3) |
O3—H3···O2 | 0.82 (4) | 1.95 (4) | 2.562 (2) | 131 (4) |
O3—H3···O7 | 0.82 (4) | 2.51 (4) | 3.072 (3) | 127 (3) |
N2—H2NA···O1Wii | 0.84 (3) | 2.00 (3) | 2.819 (3) | 164 (3) |
N3—H3N···O4 | 0.84 (3) | 2.15 (3) | 2.939 (3) | 157 (3) |
N3—H3N···O6 | 0.84 (3) | 2.44 (3) | 3.047 (3) | 130 (3) |
N2—H2NB···O8iii | 0.83 (4) | 2.41 (3) | 3.032 (3) | 132 (3) |
N2—H2NB···O9iii | 0.83 (4) | 2.21 (4) | 2.942 (3) | 147 (3) |
O4—H4A···O11iv | 0.90 (4) | 1.88 (4) | 2.732 (3) | 156 (3) |
O2W—H2WA···O8i | 0.82 (4) | 2.00 (4) | 2.819 (3) | 173 (4) |
O5—H5A···O1ii | 1.16 (4) | 1.41 (4) | 2.534 (2) | 163 (4) |
N4—H4NA···O3 | 0.88 (3) | 2.12 (3) | 2.968 (3) | 163 (3) |
O7—H7A···O12ii | 1.09 (4) | 1.39 (4) | 2.476 (2) | 174 (4) |
N4—H4NB···O2Wii | 0.83 (4) | 2.32 (4) | 3.128 (4) | 164 (3) |
N4—H4NB···O12ii | 0.83 (4) | 2.60 (4) | 2.955 (4) | 108 (3) |
O9—H9···O2W | 0.91 (3) | 1.81 (3) | 2.715 (3) | 172 (3) |
O10—H10A···O6v | 0.83 (3) | 2.19 (3) | 2.912 (3) | 145 (3) |
O10—H10A···O11 | 0.83 (3) | 2.15 (3) | 2.648 (3) | 119 (3) |
N1—H29···O10iii | 0.78 (3) | 2.24 (3) | 2.946 (3) | 151 (3) |
C5—H5···O6vi | 0.93 | 2.46 | 3.158 (3) | 132 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x−1, y−1, z−1; (iv) x−1, y−1, z; (v) x+1, y+1, z; (vi) x, y, z−1. |
Acknowledgements
The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.
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