organic compounds
of 1′-ethylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione: a hydantoine derivative
aDepartment of Chemistry, School of Engineering and Technology, Jain University, Bangalore 562 112, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, eDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, Palestinian Territories, and fDepartment of Physics, Science College, An-Najah National University, PO Box 7, Nablus, Palestinian Territories
*Correspondence e-mail: muneer@najah.edu
The title compound, C13H13N2O3, a hydantoin derivative, crystallized with two molecules (A and B) in an In molecule A, the imidazolidine ring is twisted about the C—N bond involving the spiro C atom, while in molecule B this ring is flat (r.m.s. deviation = 0.010 Å). The pyran rings in both molecules have distorted half-chair conformations. The mean plane of the imidazolidine ring is inclined to the aromatic ring of the chroman unit by 79.71 (11)° in molecule A and 82.83 (12)° in molecule B. In the crystal, pairs of N—H⋯O hydrogen bonds link the individual molecules to form A–A and B–B inversion dimers. The dimers are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming sheets lying parallel to the bc plane, viz. (011). Within the sheets, the A and B molecules are linked by C—H⋯π interactions.
Keywords: crystal structure; hydantoin derivatives; imidazolidine; chroman; spiro; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1421223
1. Related literature
For related literature on hydantoin derivatives, see: Manjunath et al. (2011, 2012).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1421223
10.1107/S2056989015016175/su5194sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock n6. DOI: 10.1107/S2056989015016175/su5194Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016175/su5194Isup3.cml
Hydantoins are important precursors in the organic synthesis of natural and non-natural amino acids, via acid-, base- or enzyme-catalyzed hydrolysis. The hydantoin nucleus, containing an active urea moiety, is well known for its diverse biological activities such as lowering blood sugar levels in mammals, and anti-inflammatory and anti-microbial activity. Considerable interest has been shown towards the synthesis and characterization of hydantoin derivatives which is a novel class of
As a part of our ongoing research on hydantoins (Manjunath et al., 2011, 2012), the synthesis, characterization and the structural work of the title compound was undertaken and herein we report on its crystal structure.The title compound, Fig. 1, an hydantoin derivative, crystallized with two molecules (A and B) in an
In molecule A the imidazolidine ring is twisted about the C9A—N2A bond, while in molecule B this ring is flat (r.m.s. deviation = 0.010 Å). The pyran rings of the chroman units in both molecules have distorted half-chair conformations. The mean plane of the imidazolidine ring is inclined to the aromatic ring of the chroman unit by 79.71 (11) ° in molecule A and 82.83 (12) ° in molecule B.In the crystal, pairs of N—H···O hydrogen bonds link the individual molecules to form A–A and B–B inversion dimers (Fig. 2 and Table 1). The dimers are linked via N—H···O and C—H···O hydrogen bonds forming sheets lying parallel to the bc plane, viz. (011); see Fig. 2 and Table 1. Within the sheets the A and B molecules are linked by C—H···π interactions (Table 1).
A solution of 3-ethyl-5-(isochromon) imidazolidine-2, 4-dione (1.0 eq) in N,N-dimethyl formamide was taken, anhydrous K2CO3 (3.0 eq) was added to the solution and stirred for 10 min. 1-bromo-ethane (1–1.1eq) was added. The reaction mixture was stirred at room temperature for 8 h and the progress monitored by TLC. Upon completion, the solvent was removed under reduced pressure and the residue was taken in water and extracted with ethyl acetate. The organic was washed with water and then and dried over anhydrous sodium sulfate. The solvent was evaporated and the crude product was purified by δ: 8.9 (s, 1H, NH), δ: 6.9(m, 3H, Ar—H) δ: 7.3 (m, 1H, Ar—H) δ: 4.5(m, 2H, CH2) δ: 2.5(m, 2H, CH2) δ: 2.3(m, 2H, CH2) δ: 1.1(m, 3H, CH3).
using chloroform: methanol (9:1) as Single crystals were obtained by slow evaporation of a solution of the title compound in ethylacetate (M.p.: 572.1 K). Spectroscopic data: H1NMR (DMSO, 400 MHz)Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. A view of the molecular structure of the two independent molecules of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A viewed along the c axis of the crystal packing of the title compound (molecule A blue, molecule B red). The dashed lines represent hydrogen bonds (see Table 1; H atoms are shown as blue and red balls). |
C13H14N2O3 | Z = 4 |
Mr = 246.26 | F(000) = 520 |
Triclinic, P1 | Dx = 1.341 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 10.2314 (16) Å | Cell parameters from 3990 reflections |
b = 11.0693 (18) Å | θ = 4.0–64.6° |
c = 11.3254 (19) Å | µ = 0.80 mm−1 |
α = 91.736 (8)° | T = 296 K |
β = 98.695 (8)° | Rectangle, green |
γ = 105.345 (8)° | 0.23 × 0.22 × 0.21 mm |
V = 1219.4 (3) Å3 |
Bruker X8 Proteum diffractometer | 3990 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 3195 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.054 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.6°, θmin = 4.0° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −12→12 |
Tmin = 0.838, Tmax = 0.850 | l = −13→13 |
14480 measured reflections |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.1316P)2 + 0.1551P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3990 reflections | Δρmax = 0.36 e Å−3 |
328 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (2) |
C13H14N2O3 | γ = 105.345 (8)° |
Mr = 246.26 | V = 1219.4 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.2314 (16) Å | Cu Kα radiation |
b = 11.0693 (18) Å | µ = 0.80 mm−1 |
c = 11.3254 (19) Å | T = 296 K |
α = 91.736 (8)° | 0.23 × 0.22 × 0.21 mm |
β = 98.695 (8)° |
Bruker X8 Proteum diffractometer | 3990 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3195 reflections with I > 2σ(I) |
Tmin = 0.838, Tmax = 0.850 | Rint = 0.054 |
14480 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.36 e Å−3 |
3990 reflections | Δρmin = −0.39 e Å−3 |
328 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1B | 0.57043 (18) | 0.04669 (17) | 0.27294 (15) | 0.0534 (5) | |
N2A | 0.88853 (16) | 0.57988 (16) | 0.41739 (15) | 0.0350 (4) | |
H2A | 0.8777 | 0.5352 | 0.4778 | 0.042* | |
O3A | 1.12385 (15) | 0.62164 (16) | 0.42909 (15) | 0.0458 (4) | |
O2A | 0.80600 (17) | 0.76449 (16) | 0.18917 (14) | 0.0492 (5) | |
C9B | 0.8442 (2) | 0.1368 (2) | 0.20830 (18) | 0.0377 (5) | |
N1B | 1.06259 (18) | 0.25381 (17) | 0.18235 (17) | 0.0421 (5) | |
O3B | 1.12728 (19) | 0.1008 (2) | 0.08118 (19) | 0.0704 (6) | |
O2B | 0.9417 (2) | 0.35827 (19) | 0.2803 (2) | 0.0767 (7) | |
C2B | 0.4752 (3) | 0.1850 (2) | 0.0004 (2) | 0.0532 (6) | |
H2B | 0.3962 | 0.1978 | −0.0437 | 0.064* | |
C1B | 0.4685 (2) | 0.1271 (2) | 0.1051 (2) | 0.0461 (6) | |
H1B | 0.3851 | 0.1010 | 0.1327 | 0.055* | |
C6B | 0.5869 (2) | 0.10716 (19) | 0.17046 (19) | 0.0364 (5) | |
C5B | 0.7129 (2) | 0.14862 (18) | 0.13279 (17) | 0.0326 (5) | |
C10B | 0.9517 (2) | 0.2642 (2) | 0.2298 (2) | 0.0428 (6) | |
C12B | 1.1849 (3) | 0.3580 (3) | 0.1783 (3) | 0.0597 (7) | |
H12A | 1.2625 | 0.3246 | 0.1728 | 0.072* | |
H12B | 1.2061 | 0.4116 | 0.2519 | 0.072* | |
C13B | 1.1641 (4) | 0.4335 (3) | 0.0750 (3) | 0.0881 (11) | |
H13A | 1.1406 | 0.3802 | 0.0022 | 0.132* | |
H13B | 1.2472 | 0.4982 | 0.0729 | 0.132* | |
H13C | 1.0911 | 0.4711 | 0.0829 | 0.132* | |
C11B | 1.0424 (2) | 0.1332 (2) | 0.1297 (2) | 0.0418 (5) | |
N2B | 0.9179 (2) | 0.06477 (17) | 0.14631 (19) | 0.0458 (5) | |
H2B1 | 0.8847 | −0.0135 | 0.1229 | 0.055* | |
C7B | 0.6800 (3) | −0.0049 (3) | 0.3177 (3) | 0.0671 (8) | |
H7B1 | 0.6795 | −0.0746 | 0.2636 | 0.081* | |
H7B2 | 0.6665 | −0.0367 | 0.3951 | 0.081* | |
C8B | 0.8153 (3) | 0.0914 (3) | 0.3303 (2) | 0.0624 (8) | |
H8B1 | 0.8875 | 0.0557 | 0.3662 | 0.075* | |
H8B2 | 0.8150 | 0.1622 | 0.3829 | 0.075* | |
C3B | 0.5997 (3) | 0.2246 (2) | −0.0401 (2) | 0.0564 (7) | |
H3B | 0.6043 | 0.2632 | −0.1117 | 0.068* | |
C4B | 0.7163 (3) | 0.2068 (2) | 0.0259 (2) | 0.0472 (6) | |
H4B | 0.7996 | 0.2343 | −0.0016 | 0.057* | |
C2A | 0.4997 (3) | 0.7412 (3) | 0.5220 (3) | 0.0669 (9) | |
H2A1 | 0.4398 | 0.7705 | 0.5619 | 0.080* | |
C1A | 0.4498 (3) | 0.6678 (3) | 0.4165 (3) | 0.0624 (8) | |
H1A | 0.3566 | 0.6473 | 0.3852 | 0.075* | |
C6A | 0.5395 (2) | 0.6243 (2) | 0.3564 (2) | 0.0426 (5) | |
C5A | 0.6788 (2) | 0.65461 (17) | 0.40196 (18) | 0.0321 (5) | |
C9A | 0.77539 (19) | 0.60575 (17) | 0.33690 (17) | 0.0301 (5) | |
C10A | 0.8545 (2) | 0.70485 (19) | 0.26353 (18) | 0.0334 (5) | |
N1A | 0.98963 (18) | 0.71123 (17) | 0.29492 (16) | 0.0379 (5) | |
C12A | 1.1017 (2) | 0.7874 (2) | 0.2399 (2) | 0.0506 (6) | |
H12C | 1.0633 | 0.8149 | 0.1652 | 0.061* | |
H12D | 1.1604 | 0.7359 | 0.2214 | 0.061* | |
C13A | 1.1862 (4) | 0.8994 (3) | 0.3188 (3) | 0.0823 (10) | |
H13D | 1.1278 | 0.9484 | 0.3410 | 0.123* | |
H13E | 1.2535 | 0.9495 | 0.2768 | 0.123* | |
H13F | 1.2317 | 0.8727 | 0.3896 | 0.123* | |
C11A | 1.0107 (2) | 0.63310 (19) | 0.38692 (18) | 0.0338 (5) | |
C8A | 0.6919 (2) | 0.4888 (2) | 0.2553 (2) | 0.0440 (5) | |
H8A1 | 0.7491 | 0.4656 | 0.2027 | 0.053* | |
H8A2 | 0.6625 | 0.4191 | 0.3039 | 0.053* | |
C7A | 0.5674 (3) | 0.5145 (2) | 0.1813 (2) | 0.0536 (6) | |
H7A1 | 0.5976 | 0.5809 | 0.1295 | 0.064* | |
H7A2 | 0.5160 | 0.4396 | 0.1308 | 0.064* | |
O1A | 0.48007 (17) | 0.55034 (18) | 0.25370 (17) | 0.0615 (5) | |
C4A | 0.7264 (3) | 0.7287 (2) | 0.5093 (2) | 0.0455 (6) | |
H4A | 0.8194 | 0.7496 | 0.5413 | 0.055* | |
C3A | 0.6370 (4) | 0.7718 (3) | 0.5691 (3) | 0.0632 (8) | |
H3A | 0.6699 | 0.8212 | 0.6408 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1B | 0.0430 (10) | 0.0677 (11) | 0.0567 (10) | 0.0183 (8) | 0.0215 (8) | 0.0207 (8) |
N2A | 0.0209 (9) | 0.0421 (9) | 0.0451 (10) | 0.0126 (7) | 0.0050 (7) | 0.0174 (7) |
O3A | 0.0213 (8) | 0.0583 (9) | 0.0611 (10) | 0.0156 (7) | 0.0050 (6) | 0.0213 (8) |
O2A | 0.0424 (10) | 0.0625 (10) | 0.0488 (9) | 0.0236 (8) | 0.0055 (7) | 0.0259 (8) |
C9B | 0.0305 (12) | 0.0451 (11) | 0.0411 (11) | 0.0170 (9) | 0.0061 (9) | −0.0006 (9) |
N1B | 0.0270 (10) | 0.0398 (9) | 0.0558 (11) | 0.0071 (8) | 0.0002 (8) | −0.0040 (8) |
O3B | 0.0336 (11) | 0.0931 (14) | 0.0857 (14) | 0.0227 (10) | 0.0111 (9) | −0.0303 (11) |
O2B | 0.0564 (13) | 0.0689 (12) | 0.0997 (16) | 0.0263 (10) | −0.0094 (10) | −0.0475 (11) |
C2B | 0.0434 (15) | 0.0453 (13) | 0.0651 (16) | 0.0159 (11) | −0.0148 (11) | −0.0012 (11) |
C1B | 0.0276 (12) | 0.0452 (12) | 0.0655 (15) | 0.0129 (9) | 0.0036 (10) | −0.0038 (11) |
C6B | 0.0328 (12) | 0.0355 (10) | 0.0421 (12) | 0.0106 (8) | 0.0084 (9) | −0.0007 (8) |
C5B | 0.0298 (11) | 0.0333 (10) | 0.0357 (10) | 0.0106 (8) | 0.0058 (8) | −0.0015 (8) |
C10B | 0.0348 (13) | 0.0447 (12) | 0.0476 (12) | 0.0170 (10) | −0.0053 (9) | −0.0139 (10) |
C12B | 0.0346 (15) | 0.0528 (14) | 0.0792 (18) | −0.0012 (11) | −0.0063 (12) | 0.0069 (13) |
C13B | 0.074 (2) | 0.075 (2) | 0.094 (2) | −0.0069 (17) | −0.0054 (18) | 0.0300 (18) |
C11B | 0.0268 (12) | 0.0500 (12) | 0.0499 (12) | 0.0164 (9) | 0.0025 (9) | −0.0078 (10) |
N2B | 0.0318 (11) | 0.0342 (9) | 0.0725 (13) | 0.0116 (7) | 0.0105 (9) | −0.0106 (9) |
C7B | 0.0629 (19) | 0.0815 (19) | 0.0674 (18) | 0.0299 (16) | 0.0187 (14) | 0.0356 (15) |
C8B | 0.0511 (17) | 0.092 (2) | 0.0509 (15) | 0.0309 (15) | 0.0064 (12) | 0.0217 (14) |
C3B | 0.0576 (17) | 0.0580 (15) | 0.0461 (14) | 0.0104 (12) | −0.0067 (11) | 0.0136 (11) |
C4B | 0.0402 (14) | 0.0547 (13) | 0.0423 (12) | 0.0055 (10) | 0.0054 (10) | 0.0088 (10) |
C2A | 0.072 (2) | 0.0721 (18) | 0.080 (2) | 0.0415 (16) | 0.0448 (17) | 0.0179 (16) |
C1A | 0.0340 (15) | 0.0741 (18) | 0.092 (2) | 0.0266 (13) | 0.0259 (13) | 0.0158 (16) |
C6A | 0.0264 (12) | 0.0478 (12) | 0.0557 (13) | 0.0132 (9) | 0.0069 (9) | 0.0077 (10) |
C5A | 0.0258 (11) | 0.0324 (9) | 0.0413 (11) | 0.0114 (8) | 0.0075 (8) | 0.0094 (8) |
C9A | 0.0208 (10) | 0.0326 (9) | 0.0379 (10) | 0.0104 (8) | 0.0010 (8) | 0.0066 (8) |
C10A | 0.0288 (11) | 0.0376 (10) | 0.0374 (10) | 0.0148 (8) | 0.0056 (8) | 0.0069 (8) |
N1A | 0.0258 (10) | 0.0475 (10) | 0.0439 (10) | 0.0124 (8) | 0.0093 (7) | 0.0179 (8) |
C12A | 0.0373 (14) | 0.0639 (15) | 0.0531 (14) | 0.0111 (11) | 0.0164 (10) | 0.0229 (12) |
C13A | 0.073 (2) | 0.0676 (18) | 0.089 (2) | −0.0131 (16) | 0.0168 (18) | 0.0178 (17) |
C11A | 0.0250 (11) | 0.0387 (10) | 0.0405 (11) | 0.0130 (8) | 0.0051 (8) | 0.0103 (8) |
C8A | 0.0361 (13) | 0.0371 (11) | 0.0572 (13) | 0.0133 (9) | −0.0016 (10) | −0.0067 (10) |
C7A | 0.0405 (15) | 0.0555 (14) | 0.0571 (15) | 0.0112 (11) | −0.0091 (11) | −0.0111 (11) |
O1A | 0.0232 (9) | 0.0751 (12) | 0.0782 (13) | 0.0112 (8) | −0.0085 (8) | −0.0123 (10) |
C4A | 0.0445 (14) | 0.0475 (12) | 0.0451 (12) | 0.0148 (10) | 0.0053 (10) | 0.0031 (10) |
C3A | 0.088 (2) | 0.0586 (15) | 0.0546 (15) | 0.0319 (15) | 0.0275 (15) | 0.0039 (12) |
O1B—C6B | 1.367 (3) | C8B—H8B1 | 0.9700 |
O1B—C7B | 1.422 (3) | C8B—H8B2 | 0.9700 |
N2A—C11A | 1.335 (3) | C3B—C4B | 1.373 (4) |
N2A—C9A | 1.458 (2) | C3B—H3B | 0.9300 |
N2A—H2A | 0.8600 | C4B—H4B | 0.9300 |
O3A—C11A | 1.224 (2) | C2A—C3A | 1.373 (5) |
O2A—C10A | 1.213 (2) | C2A—C1A | 1.373 (5) |
C9B—N2B | 1.463 (3) | C2A—H2A1 | 0.9300 |
C9B—C5B | 1.518 (3) | C1A—C6A | 1.393 (3) |
C9B—C8B | 1.528 (3) | C1A—H1A | 0.9300 |
C9B—C10B | 1.528 (3) | C6A—O1A | 1.363 (3) |
N1B—C10B | 1.356 (3) | C6A—C5A | 1.387 (3) |
N1B—C11B | 1.397 (3) | C5A—C4A | 1.392 (3) |
N1B—C12B | 1.468 (3) | C5A—C9A | 1.513 (3) |
O3B—C11B | 1.217 (3) | C9A—C10A | 1.529 (3) |
O2B—C10B | 1.208 (3) | C9A—C8A | 1.537 (3) |
C2B—C1B | 1.368 (4) | C10A—N1A | 1.356 (3) |
C2B—C3B | 1.385 (4) | N1A—C11A | 1.402 (3) |
C2B—H2B | 0.9300 | N1A—C12A | 1.467 (3) |
C1B—C6B | 1.394 (3) | C12A—C13A | 1.489 (4) |
C1B—H1B | 0.9300 | C12A—H12C | 0.9700 |
C6B—C5B | 1.386 (3) | C12A—H12D | 0.9700 |
C5B—C4B | 1.389 (3) | C13A—H13D | 0.9600 |
C12B—C13B | 1.480 (4) | C13A—H13E | 0.9600 |
C12B—H12A | 0.9700 | C13A—H13F | 0.9600 |
C12B—H12B | 0.9700 | C8A—C7A | 1.512 (3) |
C13B—H13A | 0.9600 | C8A—H8A1 | 0.9700 |
C13B—H13B | 0.9600 | C8A—H8A2 | 0.9700 |
C13B—H13C | 0.9600 | C7A—O1A | 1.421 (3) |
C11B—N2B | 1.343 (3) | C7A—H7A1 | 0.9700 |
N2B—H2B1 | 0.8600 | C7A—H7A2 | 0.9700 |
C7B—C8B | 1.491 (4) | C4A—C3A | 1.386 (4) |
C7B—H7B1 | 0.9700 | C4A—H4A | 0.9300 |
C7B—H7B2 | 0.9700 | C3A—H3A | 0.9300 |
C6B—O1B—C7B | 114.36 (18) | C3B—C4B—C5B | 121.6 (2) |
C11A—N2A—C9A | 112.58 (16) | C3B—C4B—H4B | 119.2 |
C11A—N2A—H2A | 123.7 | C5B—C4B—H4B | 119.2 |
C9A—N2A—H2A | 123.7 | C3A—C2A—C1A | 120.7 (2) |
N2B—C9B—C5B | 113.58 (17) | C3A—C2A—H2A1 | 119.7 |
N2B—C9B—C8B | 114.36 (19) | C1A—C2A—H2A1 | 119.7 |
C5B—C9B—C8B | 110.01 (18) | C2A—C1A—C6A | 119.7 (3) |
N2B—C9B—C10B | 100.06 (16) | C2A—C1A—H1A | 120.2 |
C5B—C9B—C10B | 110.45 (17) | C6A—C1A—H1A | 120.2 |
C8B—C9B—C10B | 107.8 (2) | O1A—C6A—C5A | 123.96 (19) |
C10B—N1B—C11B | 111.56 (19) | O1A—C6A—C1A | 115.4 (2) |
C10B—N1B—C12B | 124.7 (2) | C5A—C6A—C1A | 120.7 (2) |
C11B—N1B—C12B | 123.6 (2) | C6A—C5A—C4A | 118.42 (19) |
C1B—C2B—C3B | 120.0 (2) | C6A—C5A—C9A | 120.34 (19) |
C1B—C2B—H2B | 120.0 | C4A—C5A—C9A | 121.23 (18) |
C3B—C2B—H2B | 120.0 | N2A—C9A—C5A | 113.19 (16) |
C2B—C1B—C6B | 119.9 (2) | N2A—C9A—C10A | 100.66 (15) |
C2B—C1B—H1B | 120.1 | C5A—C9A—C10A | 112.17 (15) |
C6B—C1B—H1B | 120.1 | N2A—C9A—C8A | 111.52 (16) |
O1B—C6B—C5B | 122.99 (19) | C5A—C9A—C8A | 108.84 (17) |
O1B—C6B—C1B | 116.03 (19) | C10A—C9A—C8A | 110.28 (17) |
C5B—C6B—C1B | 121.0 (2) | O2A—C10A—N1A | 126.28 (19) |
C6B—C5B—C4B | 117.72 (19) | O2A—C10A—C9A | 126.74 (19) |
C6B—C5B—C9B | 121.36 (18) | N1A—C10A—C9A | 106.96 (16) |
C4B—C5B—C9B | 120.86 (19) | C10A—N1A—C11A | 111.53 (16) |
O2B—C10B—N1B | 125.3 (2) | C10A—N1A—C12A | 125.46 (17) |
O2B—C10B—C9B | 126.8 (2) | C11A—N1A—C12A | 123.00 (17) |
N1B—C10B—C9B | 107.88 (17) | N1A—C12A—C13A | 112.6 (2) |
N1B—C12B—C13B | 111.7 (2) | N1A—C12A—H12C | 109.1 |
N1B—C12B—H12A | 109.3 | C13A—C12A—H12C | 109.1 |
C13B—C12B—H12A | 109.3 | N1A—C12A—H12D | 109.1 |
N1B—C12B—H12B | 109.3 | C13A—C12A—H12D | 109.1 |
C13B—C12B—H12B | 109.3 | H12C—C12A—H12D | 107.8 |
H12A—C12B—H12B | 107.9 | C12A—C13A—H13D | 109.5 |
C12B—C13B—H13A | 109.5 | C12A—C13A—H13E | 109.5 |
C12B—C13B—H13B | 109.5 | H13D—C13A—H13E | 109.5 |
H13A—C13B—H13B | 109.5 | C12A—C13A—H13F | 109.5 |
C12B—C13B—H13C | 109.5 | H13D—C13A—H13F | 109.5 |
H13A—C13B—H13C | 109.5 | H13E—C13A—H13F | 109.5 |
H13B—C13B—H13C | 109.5 | O3A—C11A—N2A | 129.04 (18) |
O3B—C11B—N2B | 128.9 (2) | O3A—C11A—N1A | 123.54 (18) |
O3B—C11B—N1B | 123.8 (2) | N2A—C11A—N1A | 107.40 (16) |
N2B—C11B—N1B | 107.23 (17) | C7A—C8A—C9A | 110.44 (17) |
C11B—N2B—C9B | 113.24 (17) | C7A—C8A—H8A1 | 109.6 |
C11B—N2B—H2B1 | 123.4 | C9A—C8A—H8A1 | 109.6 |
C9B—N2B—H2B1 | 123.4 | C7A—C8A—H8A2 | 109.6 |
O1B—C7B—C8B | 111.1 (2) | C9A—C8A—H8A2 | 109.6 |
O1B—C7B—H7B1 | 109.4 | H8A1—C8A—H8A2 | 108.1 |
C8B—C7B—H7B1 | 109.4 | O1A—C7A—C8A | 112.2 (2) |
O1B—C7B—H7B2 | 109.4 | O1A—C7A—H7A1 | 109.2 |
C8B—C7B—H7B2 | 109.4 | C8A—C7A—H7A1 | 109.2 |
H7B1—C7B—H7B2 | 108.0 | O1A—C7A—H7A2 | 109.2 |
C7B—C8B—C9B | 110.7 (2) | C8A—C7A—H7A2 | 109.2 |
C7B—C8B—H8B1 | 109.5 | H7A1—C7A—H7A2 | 107.9 |
C9B—C8B—H8B1 | 109.5 | C6A—O1A—C7A | 118.11 (17) |
C7B—C8B—H8B2 | 109.5 | C3A—C4A—C5A | 120.9 (2) |
C9B—C8B—H8B2 | 109.5 | C3A—C4A—H4A | 119.6 |
H8B1—C8B—H8B2 | 108.1 | C5A—C4A—H4A | 119.6 |
C4B—C3B—C2B | 119.8 (2) | C2A—C3A—C4A | 119.7 (3) |
C4B—C3B—H3B | 120.1 | C2A—C3A—H3A | 120.2 |
C2B—C3B—H3B | 120.1 | C4A—C3A—H3A | 120.2 |
C3B—C2B—C1B—C6B | −0.5 (3) | C3A—C2A—C1A—C6A | −0.2 (4) |
C7B—O1B—C6B—C5B | −18.6 (3) | C2A—C1A—C6A—O1A | 178.9 (2) |
C7B—O1B—C6B—C1B | 162.2 (2) | C2A—C1A—C6A—C5A | −0.2 (4) |
C2B—C1B—C6B—O1B | −178.9 (2) | O1A—C6A—C5A—C4A | −178.5 (2) |
C2B—C1B—C6B—C5B | 1.9 (3) | C1A—C6A—C5A—C4A | 0.5 (3) |
O1B—C6B—C5B—C4B | 178.82 (19) | O1A—C6A—C5A—C9A | 0.3 (3) |
C1B—C6B—C5B—C4B | −2.1 (3) | C1A—C6A—C5A—C9A | 179.3 (2) |
O1B—C6B—C5B—C9B | −4.1 (3) | C11A—N2A—C9A—C5A | −129.41 (18) |
C1B—C6B—C5B—C9B | 175.04 (18) | C11A—N2A—C9A—C10A | −9.5 (2) |
N2B—C9B—C5B—C6B | 122.3 (2) | C11A—N2A—C9A—C8A | 107.5 (2) |
C8B—C9B—C5B—C6B | −7.3 (3) | C6A—C5A—C9A—N2A | −146.34 (19) |
C10B—C9B—C5B—C6B | −126.2 (2) | C4A—C5A—C9A—N2A | 32.5 (3) |
N2B—C9B—C5B—C4B | −60.6 (3) | C6A—C5A—C9A—C10A | 100.6 (2) |
C8B—C9B—C5B—C4B | 169.7 (2) | C4A—C5A—C9A—C10A | −80.6 (2) |
C10B—C9B—C5B—C4B | 50.9 (2) | C6A—C5A—C9A—C8A | −21.7 (2) |
C11B—N1B—C10B—O2B | −179.7 (2) | C4A—C5A—C9A—C8A | 157.10 (19) |
C12B—N1B—C10B—O2B | −4.0 (4) | N2A—C9A—C10A—O2A | −173.9 (2) |
C11B—N1B—C10B—C9B | 0.5 (2) | C5A—C9A—C10A—O2A | −53.3 (3) |
C12B—N1B—C10B—C9B | 176.2 (2) | C8A—C9A—C10A—O2A | 68.2 (3) |
N2B—C9B—C10B—O2B | −179.2 (3) | N2A—C9A—C10A—N1A | 7.7 (2) |
C5B—C9B—C10B—O2B | 60.8 (3) | C5A—C9A—C10A—N1A | 128.30 (18) |
C8B—C9B—C10B—O2B | −59.4 (3) | C8A—C9A—C10A—N1A | −110.20 (19) |
N2B—C9B—C10B—N1B | 0.6 (2) | O2A—C10A—N1A—C11A | 177.8 (2) |
C5B—C9B—C10B—N1B | −119.41 (18) | C9A—C10A—N1A—C11A | −3.8 (2) |
C8B—C9B—C10B—N1B | 120.4 (2) | O2A—C10A—N1A—C12A | −3.3 (4) |
C10B—N1B—C12B—C13B | −82.7 (3) | C9A—C10A—N1A—C12A | 175.1 (2) |
C11B—N1B—C12B—C13B | 92.5 (3) | C10A—N1A—C12A—C13A | 106.5 (3) |
C10B—N1B—C11B—O3B | −179.9 (2) | C11A—N1A—C12A—C13A | −74.7 (3) |
C12B—N1B—C11B—O3B | 4.3 (4) | C9A—N2A—C11A—O3A | −173.4 (2) |
C10B—N1B—C11B—N2B | −1.4 (3) | C9A—N2A—C11A—N1A | 7.8 (2) |
C12B—N1B—C11B—N2B | −177.2 (2) | C10A—N1A—C11A—O3A | 178.9 (2) |
O3B—C11B—N2B—C9B | −179.7 (2) | C12A—N1A—C11A—O3A | −0.0 (3) |
N1B—C11B—N2B—C9B | 1.9 (3) | C10A—N1A—C11A—N2A | −2.2 (2) |
C5B—C9B—N2B—C11B | 116.2 (2) | C12A—N1A—C11A—N2A | 178.9 (2) |
C8B—C9B—N2B—C11B | −116.4 (2) | N2A—C9A—C8A—C7A | 174.55 (19) |
C10B—C9B—N2B—C11B | −1.5 (2) | C5A—C9A—C8A—C7A | 49.0 (2) |
C6B—O1B—C7B—C8B | 52.1 (3) | C10A—C9A—C8A—C7A | −74.5 (2) |
O1B—C7B—C8B—C9B | −63.2 (3) | C9A—C8A—C7A—O1A | −58.6 (3) |
N2B—C9B—C8B—C7B | −90.4 (3) | C5A—C6A—O1A—C7A | −7.9 (3) |
C5B—C9B—C8B—C7B | 38.9 (3) | C1A—C6A—O1A—C7A | 173.1 (2) |
C10B—C9B—C8B—C7B | 159.4 (2) | C8A—C7A—O1A—C6A | 37.1 (3) |
C1B—C2B—C3B—C4B | −0.7 (4) | C6A—C5A—C4A—C3A | −0.3 (3) |
C2B—C3B—C4B—C5B | 0.5 (4) | C9A—C5A—C4A—C3A | −179.2 (2) |
C6B—C5B—C4B—C3B | 0.9 (3) | C1A—C2A—C3A—C4A | 0.3 (4) |
C9B—C5B—C4B—C3B | −176.3 (2) | C5A—C4A—C3A—C2A | −0.1 (4) |
Cg is the centroid of ring C1A–C6A. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O3Ai | 0.86 | 2.06 | 2.857 (3) | 155 |
N2B—H2B1···O3Bii | 0.86 | 2.44 | 3.019 (3) | 124 |
N2B—H2B1···O2Aiii | 0.86 | 2.55 | 3.290 (3) | 145 |
C1A—H1A···O3Aiv | 0.93 | 2.45 | 3.263 (4) | 146 |
C2B—H2B···O2Av | 0.93 | 2.58 | 3.501 (4) | 173 |
C7B—H7B2···Cgiii | 0.93 | 2.99 | 3.680 (3) | 129 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y, −z; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z. |
Cg is the centroid of ring C1A–C6A. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O3Ai | 0.86 | 2.06 | 2.857 (3) | 155 |
N2B—H2B1···O3Bii | 0.86 | 2.44 | 3.019 (3) | 124 |
N2B—H2B1···O2Aiii | 0.86 | 2.55 | 3.290 (3) | 145 |
C1A—H1A···O3Aiv | 0.93 | 2.45 | 3.263 (4) | 146 |
C2B—H2B···O2Av | 0.93 | 2.58 | 3.501 (4) | 173 |
C7B—H7B2···Cgiii | 0.93 | 2.99 | 3.680 (3) | 129 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y, −z; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z. |
Acknowledgements
The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility.
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