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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 10| October 2015| Pages o705-o706

Crystal structure of 1′-ethyl­spiro[chroman-4,4′-imidazolidine]-2′,5′-dione: a hydantoine derivative

CROSSMARK_Color_square_no_text.svg

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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 August 2015; accepted 29 August 2015; online 12 September 2015)

The title compound, C13H13N2O3, a hydantoin derivative, crystallized with two mol­ecules (A and B) in an asymmetric unit. 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 AA and BB 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.

1. Related literature

For related literature on hydantoin derivatives, see: Manjunath et al. (2011[Manjunath, H. R., Naveen, S., Ananda Kumar, C. S., Benaka Prasad, S. B., Deepa Naveen, M. V., Sridhar, M. A., Shashidhara Prasad, J. & Rangappa, K. S. (2011). J. Struct. Chem. 52, 959-963.], 2012[Manjunath, H. R., Naveen, S., Ananda Kumar, C. S., Benaka Prasad, S. B., Sridhar, M. A., Shashidhara Prasad, J. & Rangappa, K. S. (2012). J. Chem. Crystallogr. 42, 504-507.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C13H14N2O3

  • Mr = 246.26

  • Triclinic, [P \overline 1]

  • a = 10.2314 (16) Å

  • b = 11.0693 (18) Å

  • c = 11.3254 (19) Å

  • α = 91.736 (8)°

  • β = 98.695 (8)°

  • γ = 105.345 (8)°

  • V = 1219.4 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.80 mm−1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

2.2. Data collection

  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.838, Tmax = 0.850

  • 14480 measured reflections

  • 3990 independent reflections

  • 3195 reflections with I > 2σ(I)

  • Rint = 0.054

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.185

  • S = 1.04

  • 3990 reflections

  • 328 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of ring C1A–C6A.

D—H⋯A D—H H⋯A DA 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.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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 heterocyclic compounds. 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 asymmetric unit. 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).

Synthesis and crystallization top

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 column chromatography using chloro­form: methanol (9:1) as eluent. 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) 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).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atoms were fixed geometrically (N—H = 0.86 Å, C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(N,C) for other H atoms.

Related literature top

For related literature on hydantoin derivatives, see: Manjunath et al. (2011, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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).
1'-Ethylspiro[chroman-4,4'-imidazolidine]-2',5'-dione top
Crystal data top
C13H14N2O3Z = 4
Mr = 246.26F(000) = 520
Triclinic, P1Dx = 1.341 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 10.2314 (16) ÅCell parameters from 3990 reflections
b = 11.0693 (18) Åθ = 4.0–64.6°
c = 11.3254 (19) ŵ = 0.80 mm1
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
Data collection top
Bruker X8 Proteum
diffractometer
3990 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode3195 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.054
Detector resolution: 18.4 pixels mm-1θmax = 64.6°, θmin = 4.0°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1212
Tmin = 0.838, Tmax = 0.850l = 1313
14480 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-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 reflectionsΔρmax = 0.36 e Å3
328 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (2)
Crystal data top
C13H14N2O3γ = 105.345 (8)°
Mr = 246.26V = 1219.4 (3) Å3
Triclinic, P1Z = 4
a = 10.2314 (16) ÅCu Kα radiation
b = 11.0693 (18) ŵ = 0.80 mm1
c = 11.3254 (19) ÅT = 296 K
α = 91.736 (8)°0.23 × 0.22 × 0.21 mm
β = 98.695 (8)°
Data collection top
Bruker X8 Proteum
diffractometer
3990 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
3195 reflections with I > 2σ(I)
Tmin = 0.838, Tmax = 0.850Rint = 0.054
14480 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.185H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å3
3990 reflectionsΔρmin = 0.39 e Å3
328 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1B0.57043 (18)0.04669 (17)0.27294 (15)0.0534 (5)
N2A0.88853 (16)0.57988 (16)0.41739 (15)0.0350 (4)
H2A0.87770.53520.47780.042*
O3A1.12385 (15)0.62164 (16)0.42909 (15)0.0458 (4)
O2A0.80600 (17)0.76449 (16)0.18917 (14)0.0492 (5)
C9B0.8442 (2)0.1368 (2)0.20830 (18)0.0377 (5)
N1B1.06259 (18)0.25381 (17)0.18235 (17)0.0421 (5)
O3B1.12728 (19)0.1008 (2)0.08118 (19)0.0704 (6)
O2B0.9417 (2)0.35827 (19)0.2803 (2)0.0767 (7)
C2B0.4752 (3)0.1850 (2)0.0004 (2)0.0532 (6)
H2B0.39620.19780.04370.064*
C1B0.4685 (2)0.1271 (2)0.1051 (2)0.0461 (6)
H1B0.38510.10100.13270.055*
C6B0.5869 (2)0.10716 (19)0.17046 (19)0.0364 (5)
C5B0.7129 (2)0.14862 (18)0.13279 (17)0.0326 (5)
C10B0.9517 (2)0.2642 (2)0.2298 (2)0.0428 (6)
C12B1.1849 (3)0.3580 (3)0.1783 (3)0.0597 (7)
H12A1.26250.32460.17280.072*
H12B1.20610.41160.25190.072*
C13B1.1641 (4)0.4335 (3)0.0750 (3)0.0881 (11)
H13A1.14060.38020.00220.132*
H13B1.24720.49820.07290.132*
H13C1.09110.47110.08290.132*
C11B1.0424 (2)0.1332 (2)0.1297 (2)0.0418 (5)
N2B0.9179 (2)0.06477 (17)0.14631 (19)0.0458 (5)
H2B10.88470.01350.12290.055*
C7B0.6800 (3)0.0049 (3)0.3177 (3)0.0671 (8)
H7B10.67950.07460.26360.081*
H7B20.66650.03670.39510.081*
C8B0.8153 (3)0.0914 (3)0.3303 (2)0.0624 (8)
H8B10.88750.05570.36620.075*
H8B20.81500.16220.38290.075*
C3B0.5997 (3)0.2246 (2)0.0401 (2)0.0564 (7)
H3B0.60430.26320.11170.068*
C4B0.7163 (3)0.2068 (2)0.0259 (2)0.0472 (6)
H4B0.79960.23430.00160.057*
C2A0.4997 (3)0.7412 (3)0.5220 (3)0.0669 (9)
H2A10.43980.77050.56190.080*
C1A0.4498 (3)0.6678 (3)0.4165 (3)0.0624 (8)
H1A0.35660.64730.38520.075*
C6A0.5395 (2)0.6243 (2)0.3564 (2)0.0426 (5)
C5A0.6788 (2)0.65461 (17)0.40196 (18)0.0321 (5)
C9A0.77539 (19)0.60575 (17)0.33690 (17)0.0301 (5)
C10A0.8545 (2)0.70485 (19)0.26353 (18)0.0334 (5)
N1A0.98963 (18)0.71123 (17)0.29492 (16)0.0379 (5)
C12A1.1017 (2)0.7874 (2)0.2399 (2)0.0506 (6)
H12C1.06330.81490.16520.061*
H12D1.16040.73590.22140.061*
C13A1.1862 (4)0.8994 (3)0.3188 (3)0.0823 (10)
H13D1.12780.94840.34100.123*
H13E1.25350.94950.27680.123*
H13F1.23170.87270.38960.123*
C11A1.0107 (2)0.63310 (19)0.38692 (18)0.0338 (5)
C8A0.6919 (2)0.4888 (2)0.2553 (2)0.0440 (5)
H8A10.74910.46560.20270.053*
H8A20.66250.41910.30390.053*
C7A0.5674 (3)0.5145 (2)0.1813 (2)0.0536 (6)
H7A10.59760.58090.12950.064*
H7A20.51600.43960.13080.064*
O1A0.48007 (17)0.55034 (18)0.25370 (17)0.0615 (5)
C4A0.7264 (3)0.7287 (2)0.5093 (2)0.0455 (6)
H4A0.81940.74960.54130.055*
C3A0.6370 (4)0.7718 (3)0.5691 (3)0.0632 (8)
H3A0.66990.82120.64080.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1B0.0430 (10)0.0677 (11)0.0567 (10)0.0183 (8)0.0215 (8)0.0207 (8)
N2A0.0209 (9)0.0421 (9)0.0451 (10)0.0126 (7)0.0050 (7)0.0174 (7)
O3A0.0213 (8)0.0583 (9)0.0611 (10)0.0156 (7)0.0050 (6)0.0213 (8)
O2A0.0424 (10)0.0625 (10)0.0488 (9)0.0236 (8)0.0055 (7)0.0259 (8)
C9B0.0305 (12)0.0451 (11)0.0411 (11)0.0170 (9)0.0061 (9)0.0006 (9)
N1B0.0270 (10)0.0398 (9)0.0558 (11)0.0071 (8)0.0002 (8)0.0040 (8)
O3B0.0336 (11)0.0931 (14)0.0857 (14)0.0227 (10)0.0111 (9)0.0303 (11)
O2B0.0564 (13)0.0689 (12)0.0997 (16)0.0263 (10)0.0094 (10)0.0475 (11)
C2B0.0434 (15)0.0453 (13)0.0651 (16)0.0159 (11)0.0148 (11)0.0012 (11)
C1B0.0276 (12)0.0452 (12)0.0655 (15)0.0129 (9)0.0036 (10)0.0038 (11)
C6B0.0328 (12)0.0355 (10)0.0421 (12)0.0106 (8)0.0084 (9)0.0007 (8)
C5B0.0298 (11)0.0333 (10)0.0357 (10)0.0106 (8)0.0058 (8)0.0015 (8)
C10B0.0348 (13)0.0447 (12)0.0476 (12)0.0170 (10)0.0053 (9)0.0139 (10)
C12B0.0346 (15)0.0528 (14)0.0792 (18)0.0012 (11)0.0063 (12)0.0069 (13)
C13B0.074 (2)0.075 (2)0.094 (2)0.0069 (17)0.0054 (18)0.0300 (18)
C11B0.0268 (12)0.0500 (12)0.0499 (12)0.0164 (9)0.0025 (9)0.0078 (10)
N2B0.0318 (11)0.0342 (9)0.0725 (13)0.0116 (7)0.0105 (9)0.0106 (9)
C7B0.0629 (19)0.0815 (19)0.0674 (18)0.0299 (16)0.0187 (14)0.0356 (15)
C8B0.0511 (17)0.092 (2)0.0509 (15)0.0309 (15)0.0064 (12)0.0217 (14)
C3B0.0576 (17)0.0580 (15)0.0461 (14)0.0104 (12)0.0067 (11)0.0136 (11)
C4B0.0402 (14)0.0547 (13)0.0423 (12)0.0055 (10)0.0054 (10)0.0088 (10)
C2A0.072 (2)0.0721 (18)0.080 (2)0.0415 (16)0.0448 (17)0.0179 (16)
C1A0.0340 (15)0.0741 (18)0.092 (2)0.0266 (13)0.0259 (13)0.0158 (16)
C6A0.0264 (12)0.0478 (12)0.0557 (13)0.0132 (9)0.0069 (9)0.0077 (10)
C5A0.0258 (11)0.0324 (9)0.0413 (11)0.0114 (8)0.0075 (8)0.0094 (8)
C9A0.0208 (10)0.0326 (9)0.0379 (10)0.0104 (8)0.0010 (8)0.0066 (8)
C10A0.0288 (11)0.0376 (10)0.0374 (10)0.0148 (8)0.0056 (8)0.0069 (8)
N1A0.0258 (10)0.0475 (10)0.0439 (10)0.0124 (8)0.0093 (7)0.0179 (8)
C12A0.0373 (14)0.0639 (15)0.0531 (14)0.0111 (11)0.0164 (10)0.0229 (12)
C13A0.073 (2)0.0676 (18)0.089 (2)0.0131 (16)0.0168 (18)0.0178 (17)
C11A0.0250 (11)0.0387 (10)0.0405 (11)0.0130 (8)0.0051 (8)0.0103 (8)
C8A0.0361 (13)0.0371 (11)0.0572 (13)0.0133 (9)0.0016 (10)0.0067 (10)
C7A0.0405 (15)0.0555 (14)0.0571 (15)0.0112 (11)0.0091 (11)0.0111 (11)
O1A0.0232 (9)0.0751 (12)0.0782 (13)0.0112 (8)0.0085 (8)0.0123 (10)
C4A0.0445 (14)0.0475 (12)0.0451 (12)0.0148 (10)0.0053 (10)0.0031 (10)
C3A0.088 (2)0.0586 (15)0.0546 (15)0.0319 (15)0.0275 (15)0.0039 (12)
Geometric parameters (Å, º) top
O1B—C6B1.367 (3)C8B—H8B10.9700
O1B—C7B1.422 (3)C8B—H8B20.9700
N2A—C11A1.335 (3)C3B—C4B1.373 (4)
N2A—C9A1.458 (2)C3B—H3B0.9300
N2A—H2A0.8600C4B—H4B0.9300
O3A—C11A1.224 (2)C2A—C3A1.373 (5)
O2A—C10A1.213 (2)C2A—C1A1.373 (5)
C9B—N2B1.463 (3)C2A—H2A10.9300
C9B—C5B1.518 (3)C1A—C6A1.393 (3)
C9B—C8B1.528 (3)C1A—H1A0.9300
C9B—C10B1.528 (3)C6A—O1A1.363 (3)
N1B—C10B1.356 (3)C6A—C5A1.387 (3)
N1B—C11B1.397 (3)C5A—C4A1.392 (3)
N1B—C12B1.468 (3)C5A—C9A1.513 (3)
O3B—C11B1.217 (3)C9A—C10A1.529 (3)
O2B—C10B1.208 (3)C9A—C8A1.537 (3)
C2B—C1B1.368 (4)C10A—N1A1.356 (3)
C2B—C3B1.385 (4)N1A—C11A1.402 (3)
C2B—H2B0.9300N1A—C12A1.467 (3)
C1B—C6B1.394 (3)C12A—C13A1.489 (4)
C1B—H1B0.9300C12A—H12C0.9700
C6B—C5B1.386 (3)C12A—H12D0.9700
C5B—C4B1.389 (3)C13A—H13D0.9600
C12B—C13B1.480 (4)C13A—H13E0.9600
C12B—H12A0.9700C13A—H13F0.9600
C12B—H12B0.9700C8A—C7A1.512 (3)
C13B—H13A0.9600C8A—H8A10.9700
C13B—H13B0.9600C8A—H8A20.9700
C13B—H13C0.9600C7A—O1A1.421 (3)
C11B—N2B1.343 (3)C7A—H7A10.9700
N2B—H2B10.8600C7A—H7A20.9700
C7B—C8B1.491 (4)C4A—C3A1.386 (4)
C7B—H7B10.9700C4A—H4A0.9300
C7B—H7B20.9700C3A—H3A0.9300
C6B—O1B—C7B114.36 (18)C3B—C4B—C5B121.6 (2)
C11A—N2A—C9A112.58 (16)C3B—C4B—H4B119.2
C11A—N2A—H2A123.7C5B—C4B—H4B119.2
C9A—N2A—H2A123.7C3A—C2A—C1A120.7 (2)
N2B—C9B—C5B113.58 (17)C3A—C2A—H2A1119.7
N2B—C9B—C8B114.36 (19)C1A—C2A—H2A1119.7
C5B—C9B—C8B110.01 (18)C2A—C1A—C6A119.7 (3)
N2B—C9B—C10B100.06 (16)C2A—C1A—H1A120.2
C5B—C9B—C10B110.45 (17)C6A—C1A—H1A120.2
C8B—C9B—C10B107.8 (2)O1A—C6A—C5A123.96 (19)
C10B—N1B—C11B111.56 (19)O1A—C6A—C1A115.4 (2)
C10B—N1B—C12B124.7 (2)C5A—C6A—C1A120.7 (2)
C11B—N1B—C12B123.6 (2)C6A—C5A—C4A118.42 (19)
C1B—C2B—C3B120.0 (2)C6A—C5A—C9A120.34 (19)
C1B—C2B—H2B120.0C4A—C5A—C9A121.23 (18)
C3B—C2B—H2B120.0N2A—C9A—C5A113.19 (16)
C2B—C1B—C6B119.9 (2)N2A—C9A—C10A100.66 (15)
C2B—C1B—H1B120.1C5A—C9A—C10A112.17 (15)
C6B—C1B—H1B120.1N2A—C9A—C8A111.52 (16)
O1B—C6B—C5B122.99 (19)C5A—C9A—C8A108.84 (17)
O1B—C6B—C1B116.03 (19)C10A—C9A—C8A110.28 (17)
C5B—C6B—C1B121.0 (2)O2A—C10A—N1A126.28 (19)
C6B—C5B—C4B117.72 (19)O2A—C10A—C9A126.74 (19)
C6B—C5B—C9B121.36 (18)N1A—C10A—C9A106.96 (16)
C4B—C5B—C9B120.86 (19)C10A—N1A—C11A111.53 (16)
O2B—C10B—N1B125.3 (2)C10A—N1A—C12A125.46 (17)
O2B—C10B—C9B126.8 (2)C11A—N1A—C12A123.00 (17)
N1B—C10B—C9B107.88 (17)N1A—C12A—C13A112.6 (2)
N1B—C12B—C13B111.7 (2)N1A—C12A—H12C109.1
N1B—C12B—H12A109.3C13A—C12A—H12C109.1
C13B—C12B—H12A109.3N1A—C12A—H12D109.1
N1B—C12B—H12B109.3C13A—C12A—H12D109.1
C13B—C12B—H12B109.3H12C—C12A—H12D107.8
H12A—C12B—H12B107.9C12A—C13A—H13D109.5
C12B—C13B—H13A109.5C12A—C13A—H13E109.5
C12B—C13B—H13B109.5H13D—C13A—H13E109.5
H13A—C13B—H13B109.5C12A—C13A—H13F109.5
C12B—C13B—H13C109.5H13D—C13A—H13F109.5
H13A—C13B—H13C109.5H13E—C13A—H13F109.5
H13B—C13B—H13C109.5O3A—C11A—N2A129.04 (18)
O3B—C11B—N2B128.9 (2)O3A—C11A—N1A123.54 (18)
O3B—C11B—N1B123.8 (2)N2A—C11A—N1A107.40 (16)
N2B—C11B—N1B107.23 (17)C7A—C8A—C9A110.44 (17)
C11B—N2B—C9B113.24 (17)C7A—C8A—H8A1109.6
C11B—N2B—H2B1123.4C9A—C8A—H8A1109.6
C9B—N2B—H2B1123.4C7A—C8A—H8A2109.6
O1B—C7B—C8B111.1 (2)C9A—C8A—H8A2109.6
O1B—C7B—H7B1109.4H8A1—C8A—H8A2108.1
C8B—C7B—H7B1109.4O1A—C7A—C8A112.2 (2)
O1B—C7B—H7B2109.4O1A—C7A—H7A1109.2
C8B—C7B—H7B2109.4C8A—C7A—H7A1109.2
H7B1—C7B—H7B2108.0O1A—C7A—H7A2109.2
C7B—C8B—C9B110.7 (2)C8A—C7A—H7A2109.2
C7B—C8B—H8B1109.5H7A1—C7A—H7A2107.9
C9B—C8B—H8B1109.5C6A—O1A—C7A118.11 (17)
C7B—C8B—H8B2109.5C3A—C4A—C5A120.9 (2)
C9B—C8B—H8B2109.5C3A—C4A—H4A119.6
H8B1—C8B—H8B2108.1C5A—C4A—H4A119.6
C4B—C3B—C2B119.8 (2)C2A—C3A—C4A119.7 (3)
C4B—C3B—H3B120.1C2A—C3A—H3A120.2
C2B—C3B—H3B120.1C4A—C3A—H3A120.2
C3B—C2B—C1B—C6B0.5 (3)C3A—C2A—C1A—C6A0.2 (4)
C7B—O1B—C6B—C5B18.6 (3)C2A—C1A—C6A—O1A178.9 (2)
C7B—O1B—C6B—C1B162.2 (2)C2A—C1A—C6A—C5A0.2 (4)
C2B—C1B—C6B—O1B178.9 (2)O1A—C6A—C5A—C4A178.5 (2)
C2B—C1B—C6B—C5B1.9 (3)C1A—C6A—C5A—C4A0.5 (3)
O1B—C6B—C5B—C4B178.82 (19)O1A—C6A—C5A—C9A0.3 (3)
C1B—C6B—C5B—C4B2.1 (3)C1A—C6A—C5A—C9A179.3 (2)
O1B—C6B—C5B—C9B4.1 (3)C11A—N2A—C9A—C5A129.41 (18)
C1B—C6B—C5B—C9B175.04 (18)C11A—N2A—C9A—C10A9.5 (2)
N2B—C9B—C5B—C6B122.3 (2)C11A—N2A—C9A—C8A107.5 (2)
C8B—C9B—C5B—C6B7.3 (3)C6A—C5A—C9A—N2A146.34 (19)
C10B—C9B—C5B—C6B126.2 (2)C4A—C5A—C9A—N2A32.5 (3)
N2B—C9B—C5B—C4B60.6 (3)C6A—C5A—C9A—C10A100.6 (2)
C8B—C9B—C5B—C4B169.7 (2)C4A—C5A—C9A—C10A80.6 (2)
C10B—C9B—C5B—C4B50.9 (2)C6A—C5A—C9A—C8A21.7 (2)
C11B—N1B—C10B—O2B179.7 (2)C4A—C5A—C9A—C8A157.10 (19)
C12B—N1B—C10B—O2B4.0 (4)N2A—C9A—C10A—O2A173.9 (2)
C11B—N1B—C10B—C9B0.5 (2)C5A—C9A—C10A—O2A53.3 (3)
C12B—N1B—C10B—C9B176.2 (2)C8A—C9A—C10A—O2A68.2 (3)
N2B—C9B—C10B—O2B179.2 (3)N2A—C9A—C10A—N1A7.7 (2)
C5B—C9B—C10B—O2B60.8 (3)C5A—C9A—C10A—N1A128.30 (18)
C8B—C9B—C10B—O2B59.4 (3)C8A—C9A—C10A—N1A110.20 (19)
N2B—C9B—C10B—N1B0.6 (2)O2A—C10A—N1A—C11A177.8 (2)
C5B—C9B—C10B—N1B119.41 (18)C9A—C10A—N1A—C11A3.8 (2)
C8B—C9B—C10B—N1B120.4 (2)O2A—C10A—N1A—C12A3.3 (4)
C10B—N1B—C12B—C13B82.7 (3)C9A—C10A—N1A—C12A175.1 (2)
C11B—N1B—C12B—C13B92.5 (3)C10A—N1A—C12A—C13A106.5 (3)
C10B—N1B—C11B—O3B179.9 (2)C11A—N1A—C12A—C13A74.7 (3)
C12B—N1B—C11B—O3B4.3 (4)C9A—N2A—C11A—O3A173.4 (2)
C10B—N1B—C11B—N2B1.4 (3)C9A—N2A—C11A—N1A7.8 (2)
C12B—N1B—C11B—N2B177.2 (2)C10A—N1A—C11A—O3A178.9 (2)
O3B—C11B—N2B—C9B179.7 (2)C12A—N1A—C11A—O3A0.0 (3)
N1B—C11B—N2B—C9B1.9 (3)C10A—N1A—C11A—N2A2.2 (2)
C5B—C9B—N2B—C11B116.2 (2)C12A—N1A—C11A—N2A178.9 (2)
C8B—C9B—N2B—C11B116.4 (2)N2A—C9A—C8A—C7A174.55 (19)
C10B—C9B—N2B—C11B1.5 (2)C5A—C9A—C8A—C7A49.0 (2)
C6B—O1B—C7B—C8B52.1 (3)C10A—C9A—C8A—C7A74.5 (2)
O1B—C7B—C8B—C9B63.2 (3)C9A—C8A—C7A—O1A58.6 (3)
N2B—C9B—C8B—C7B90.4 (3)C5A—C6A—O1A—C7A7.9 (3)
C5B—C9B—C8B—C7B38.9 (3)C1A—C6A—O1A—C7A173.1 (2)
C10B—C9B—C8B—C7B159.4 (2)C8A—C7A—O1A—C6A37.1 (3)
C1B—C2B—C3B—C4B0.7 (4)C6A—C5A—C4A—C3A0.3 (3)
C2B—C3B—C4B—C5B0.5 (4)C9A—C5A—C4A—C3A179.2 (2)
C6B—C5B—C4B—C3B0.9 (3)C1A—C2A—C3A—C4A0.3 (4)
C9B—C5B—C4B—C3B176.3 (2)C5A—C4A—C3A—C2A0.1 (4)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of ring C1A–C6A.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O3Ai0.862.062.857 (3)155
N2B—H2B1···O3Bii0.862.443.019 (3)124
N2B—H2B1···O2Aiii0.862.553.290 (3)145
C1A—H1A···O3Aiv0.932.453.263 (4)146
C2B—H2B···O2Av0.932.583.501 (4)173
C7B—H7B2···Cgiii0.932.993.680 (3)129
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y, z; (iii) x, y1, z; (iv) x1, y, z; (v) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of ring C1A–C6A.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O3Ai0.862.062.857 (3)155
N2B—H2B1···O3Bii0.862.443.019 (3)124
N2B—H2B1···O2Aiii0.862.553.290 (3)145
C1A—H1A···O3Aiv0.932.453.263 (4)146
C2B—H2B···O2Av0.932.583.501 (4)173
C7B—H7B2···Cgiii0.932.993.680 (3)129
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y, z; (iii) x, y1, z; (iv) x1, 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.

References

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Volume 71| Part 10| October 2015| Pages o705-o706
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