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ISSN: 2056-9890

A triclinic polymorph of (E)-2-(4-iso­butyl­phen­yl)-N′-[1-(4-nitro­phen­yl)ethyl­­idene]propano­hydrazide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India, bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore, 570 006, India, and cDepartment of Physics, St Philomena's College, Mysore, 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 8 June 2013; accepted 18 July 2013; online 27 July 2013)

The asymmetric unit of the triclinic polymorph of the title compound, C21H25N3O3, consists of two mol­ecules, whereas for the monoclinic polymorph Z′ = 1 [Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445.]). Acta Cryst. E65, o445]. The two mol­ecules exhibit an E configuration with respect to the C=N bond. The mol­ecules are linked into dimers by N—H⋯O and C—H⋯O hydrogen bonds forming R22(8) ring motifs. In addition, ππ inter­actions occur between nitro­phenyl groups [minimum centroid–centroid distance 3.940 (2) Å], stacking the molecules along the ac plane.

Related literature

For the structure of the monoclinic polymorph of the title compound, see: Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the pharmacological activity of hydrazones, see: Bedia et al. (2006[Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.]); Rollas et al. (2002[Rollas, S., Gulerman, N. & Erdeniz, H. (2002). Il Farmaco, 57, 171-174.]); Terzioglu & Gursoy (2003[Terzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781-786.]).

[Scheme 1]

Experimental

Crystal data
  • C21H25N3O3

  • Mr = 367.44

  • Triclinic, [P \overline 1]

  • a = 12.201 (5) Å

  • b = 13.429 (5) Å

  • c = 13.932 (5) Å

  • α = 90.470 (7)°

  • β = 110.099 (6)°

  • γ = 107.321 (6)°

  • V = 2030.9 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 300 K

  • 0.23 × 0.22 × 0.22 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 21740 measured reflections

  • 8844 independent reflections

  • 4673 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.193

  • S = 1.02

  • 8844 reflections

  • 495 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O1Bi 0.86 2.14 2.977 (3) 165
N1B—H1B⋯O1Aii 0.86 2.15 2.919 (3) 149
C15A—H15C⋯O1Bi 0.96 2.41 3.252 (4) 147
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information


Comment top

Hydrazone derivatives show divers pharmacological activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gursoy, 2003).

The asymmetric unit of the title compound consists of the A and B molecules (Fig. 1 & Fig. 2) and they show E configuration with respect to the C14=N2 bond. The molecular fragment composed of the atoms C11,C13,O1,N1,N2,C14,C15 is nearly planar, with the maximum deviation of 0.041 (3) Å for C15. It makes dihedral angles of 87.50 (14)°, 5.26 (14) ° and 42.43 (12) ° and 13.94 (12) ° with the terminal benzene rings in molecules B and A, respectively. The dihedral angle between nitrophenyl and phenyl groups are 87.64 (12)° and 74.31 ° for molecule B and A, respectively. These dihedral angles show that the two molecules differ in conformation. The bond lengths and bond angles are comparable to those in the monoclinic polymorph (Fun et al., 2009).

The molecules are connected by N—H···O and C—H···O hydrogen bonds with R22(8) ring motifs (Bernstein et al., 1995) (Table 1 and Fig. 3). An intermolecular π···π interaction (Cg2 and Cg4; Cg4 and Cg4) is observed. The distance between Cg2 and Cg4 is 3.940 (3) Å and between Cg4 and Cg4 is 3.979 (3) Å. (Cg2 is C16A/C17A/C18A/C19A/C20A/C21A centroid and Cg4 is C16B/C17B/C18B/C19B/C20B/C21B centroid). This interaction generates stacking of molecules along the ac plane.

Related literature top

For the structure of the monoclinic polymorph of the title compound, see: Fun et al. (2009). For graph-set notation, see: Bernstein et al. (1995). For the pharmacological activity of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002); Terzioglu & Gursoy (2003).

Experimental top

The title compound is prepared by heating 2-(4-isobutylphenyl)propanehydrazide (0.01 mol) with p-nitroacetophenone(0.01 mol), in the presence of catalytic amount of acetic acid, in ethanol (20 ml) at reflux temperature for 5 h. Solid compound was obtained by filtration, washed with ice cold water and dried. The title compound was crystallized by slow evaporation of ethanol and acetonitrile (m.p. 442 K).

Refinement top

All the H atoms were placed in calculated positions, with N—H = 0.86 Å, Uiso (H) = 1.2 Ueq(N) for NH, C–H = 0.93 Å, Uiso (H) = 1.2 Ueq(C) for aromatic and C–H = 0.97 Å, Uiso (H) = 1.2 Ueq(C) for CH2, Uiso (H) = 1.5 Ueq(C) for CH3 atoms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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).

Figures top
[Figure 1] Fig. 1. Molecule A of the title compound with displacement ellipsoids shown at the 50% probability level.
[Figure 2] Fig. 2. Molecule B of the title compound with displacement ellipsoids shown at the 50% probability level.
[Figure 3] Fig. 3. Packing diagram viewed along the crystallographic a axis. Dotted lines represent intermolecular N-H···O hydrogen bonding. Hydrogen atoms are not involved in the interactions were removed for clarity.
(E)-2-(4-Isobutylphenyl)-N'-[1-(4-nitrophenyl)ethylidene]propanohydrazide top
Crystal data top
C21H25N3O3Z = 4
Mr = 367.44F(000) = 784
Triclinic, P1Dx = 1.202 Mg m3
Hall symbol: -P 1Melting point: 442 K
a = 12.201 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.429 (5) ÅCell parameters from 8844 reflections
c = 13.932 (5) Åθ = 1.6–27.1°
α = 90.470 (7)°µ = 0.08 mm1
β = 110.099 (6)°T = 300 K
γ = 107.321 (6)°Block, colorless
V = 2030.9 (13) Å30.23 × 0.22 × 0.22 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
4673 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.1°, θmin = 1.6°
Detector resolution: 16.0839 pixels mm-1h = 1515
ω scansk = 1717
21740 measured reflectionsl = 1717
8844 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0752P)2 + 0.3062P]
where P = (Fo2 + 2Fc2)/3
8844 reflections(Δ/σ)max = 0.004
495 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C21H25N3O3γ = 107.321 (6)°
Mr = 367.44V = 2030.9 (13) Å3
Triclinic, P1Z = 4
a = 12.201 (5) ÅMo Kα radiation
b = 13.429 (5) ŵ = 0.08 mm1
c = 13.932 (5) ÅT = 300 K
α = 90.470 (7)°0.23 × 0.22 × 0.22 mm
β = 110.099 (6)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
4673 reflections with I > 2σ(I)
21740 measured reflectionsRint = 0.039
8844 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.193H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
8844 reflectionsΔρmin = 0.16 e Å3
495 parameters
Special details top

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1A0.84024 (16)0.14913 (15)0.55714 (13)0.0761 (7)
O2A0.7121 (2)0.3312 (2)0.70085 (17)0.1031 (10)
O3A0.6171 (2)0.44110 (17)0.63494 (17)0.0948 (9)
N1A0.71527 (17)0.05635 (16)0.48633 (14)0.0577 (7)
N2A0.67981 (18)0.03078 (15)0.49209 (14)0.0551 (7)
N3A0.6410 (2)0.3595 (2)0.6291 (2)0.0756 (10)
C1A0.6003 (4)0.1837 (3)0.9456 (3)0.1231 (18)
C2A0.6171 (4)0.0619 (4)1.0906 (3)0.134 (2)
C3A0.6444 (4)0.0725 (3)0.9916 (3)0.1029 (16)
C4A0.7774 (3)0.0140 (3)1.0121 (2)0.1044 (15)
C5A0.8123 (3)0.0023 (3)0.9175 (2)0.0768 (10)
C6A0.8563 (3)0.0728 (3)0.8837 (2)0.0910 (15)
C7A0.8846 (3)0.0651 (2)0.7957 (2)0.0797 (11)
C8A0.8700 (2)0.0160 (2)0.73670 (17)0.0563 (8)
C9A0.8267 (2)0.0874 (2)0.77044 (19)0.0639 (9)
C10A0.7972 (2)0.0782 (2)0.8581 (2)0.0729 (10)
C11A0.9017 (2)0.0263 (2)0.64037 (18)0.0592 (8)
C12A1.0355 (2)0.0331 (2)0.6613 (2)0.0848 (11)
C13A0.8170 (2)0.0664 (2)0.55925 (18)0.0572 (9)
C14A0.5906 (2)0.04170 (19)0.41559 (17)0.0530 (8)
C15A0.5237 (3)0.0325 (2)0.31726 (19)0.0773 (10)
C16A0.5552 (2)0.13587 (19)0.42770 (17)0.0524 (8)
C17A0.4665 (2)0.1624 (2)0.34890 (19)0.0698 (10)
C18A0.4373 (3)0.2526 (3)0.3600 (2)0.0838 (11)
C19A0.4939 (3)0.3181 (2)0.4514 (2)0.0733 (11)
C20A0.5797 (2)0.2901 (2)0.53021 (19)0.0600 (9)
C21A0.6115 (2)0.2023 (2)0.52082 (17)0.0561 (8)
O1B0.60116 (16)0.75492 (14)0.32931 (12)0.0678 (6)
O2B0.7193 (3)0.2616 (2)0.2322 (2)0.1500 (15)
O3B0.8201 (3)0.1626 (2)0.3011 (2)0.1580 (16)
N1B0.70320 (18)0.65361 (16)0.42081 (14)0.0575 (7)
N2B0.73709 (17)0.56469 (16)0.42424 (14)0.0544 (7)
N3B0.7882 (3)0.2379 (2)0.3055 (2)0.0912 (12)
C1B1.0431 (3)0.6854 (3)0.0762 (3)0.1043 (17)
C2B0.8173 (3)0.6347 (3)0.1156 (2)0.1057 (15)
C3B0.9435 (3)0.6789 (2)0.0323 (2)0.0760 (11)
C4B0.9575 (3)0.6178 (3)0.0603 (2)0.0843 (12)
C5B0.8631 (3)0.6109 (2)0.10965 (18)0.0642 (10)
C6B0.8514 (2)0.6997 (2)0.14981 (19)0.0661 (10)
C7B0.7625 (2)0.6943 (2)0.19134 (17)0.0601 (9)
C8B0.6818 (2)0.59888 (19)0.19621 (15)0.0515 (8)
C9B0.6943 (3)0.5099 (2)0.15785 (18)0.0674 (10)
C10B0.7823 (3)0.5158 (2)0.11506 (19)0.0727 (11)
C11B0.5795 (2)0.59323 (19)0.23640 (16)0.0552 (8)
C12B0.4704 (2)0.6125 (2)0.15221 (19)0.0760 (10)
C13B0.6271 (2)0.6736 (2)0.33137 (17)0.0544 (8)
C14B0.8072 (2)0.5478 (2)0.51048 (17)0.0560 (8)
C15B0.8537 (3)0.6172 (2)0.61121 (18)0.0788 (10)
C16B0.8429 (2)0.4523 (2)0.50529 (18)0.0587 (9)
C17B0.9217 (2)0.4223 (3)0.5904 (2)0.0757 (10)
C18B0.9561 (3)0.3350 (3)0.5827 (3)0.0888 (14)
C19B0.9135 (3)0.2737 (3)0.4908 (3)0.0844 (14)
C20B0.8343 (2)0.3021 (2)0.4058 (2)0.0683 (10)
C21B0.7998 (2)0.3889 (2)0.41132 (19)0.0616 (9)
H1A0.672100.105300.435600.0690*
H4A10.827400.050201.058700.1250*
H3A0.596300.036200.941600.1230*
H4A20.797500.055501.046800.1250*
H6A0.867600.128100.921500.1090*
H7A0.913900.115100.775600.0960*
H9A0.816800.143500.733400.0770*
H10A0.766500.127400.877700.0880*
H1A10.618700.187500.884300.1850*
H11A0.889100.090700.613000.0710*
H1A20.512900.212000.928700.1850*
H12D1.047600.031900.682300.1270*
H12E1.089500.089400.715100.1270*
H12F1.053300.046100.599800.1270*
H1A30.640700.223600.994200.1850*
H2A10.666700.092301.143500.2010*
H2A20.531600.097801.077000.2010*
H15A0.510600.007100.259700.1160*
H15B0.445600.076400.317400.1160*
H15C0.572000.075600.311900.1160*
H2A30.636200.011101.113000.2010*
H17A0.425500.118300.286900.0840*
H18A0.378800.269200.305100.1010*
H19A0.474900.378900.459800.0880*
H21A0.670300.186700.576100.0670*
H4B10.952200.547100.038800.1010*
H1B0.730300.697100.475700.0690*
H4B21.039000.650700.111700.1010*
H3B0.952900.750900.008400.0910*
H2B10.811000.677600.170800.1590*
H2B20.755400.634200.087600.1590*
H6B0.905000.765200.148800.0790*
H2B30.805400.564300.141400.1590*
H7B0.756700.756100.216600.0720*
H1B11.027600.618100.111600.1560*
H1B21.122000.705200.021200.1560*
H9B0.642300.444300.160800.0810*
H1B31.042700.737000.123500.1560*
H10B0.787400.454000.089100.0880*
H11B0.551600.522800.255900.0660*
H12A0.496300.681800.133300.1140*
H12B0.405100.606300.177700.1140*
H12C0.441500.561400.093000.1140*
H15D0.907700.684300.607200.1180*
H15E0.897700.584800.665800.1180*
H15F0.785100.626700.624700.1180*
H17B0.951800.462600.654100.0910*
H18B1.009100.317500.640900.1070*
H19B0.936800.214600.485300.1010*
H210.747400.406100.352500.0740*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0714 (12)0.0606 (12)0.0770 (12)0.0225 (10)0.0029 (9)0.0123 (9)
O2A0.0921 (16)0.131 (2)0.0766 (14)0.0391 (15)0.0172 (12)0.0294 (13)
O3A0.1093 (17)0.0687 (15)0.1118 (16)0.0122 (13)0.0610 (14)0.0153 (12)
N1A0.0541 (12)0.0579 (13)0.0511 (11)0.0133 (10)0.0112 (9)0.0054 (9)
N2A0.0577 (12)0.0543 (13)0.0531 (11)0.0167 (10)0.0210 (10)0.0019 (9)
N3A0.0684 (16)0.0825 (19)0.0784 (17)0.0090 (14)0.0431 (14)0.0097 (14)
C1A0.120 (3)0.147 (4)0.077 (2)0.010 (3)0.033 (2)0.014 (2)
C2A0.175 (4)0.166 (4)0.109 (3)0.078 (3)0.090 (3)0.040 (3)
C3A0.119 (3)0.125 (3)0.084 (2)0.053 (3)0.048 (2)0.029 (2)
C4A0.112 (3)0.131 (3)0.0567 (17)0.028 (2)0.0239 (18)0.0022 (18)
C5A0.0759 (18)0.088 (2)0.0513 (15)0.0187 (17)0.0113 (13)0.0007 (15)
C6A0.112 (3)0.094 (3)0.0698 (19)0.046 (2)0.0249 (18)0.0283 (17)
C7A0.096 (2)0.078 (2)0.0737 (18)0.0449 (18)0.0266 (16)0.0120 (16)
C8A0.0483 (13)0.0552 (16)0.0519 (13)0.0136 (12)0.0047 (11)0.0004 (11)
C9A0.0660 (16)0.0578 (17)0.0594 (15)0.0199 (13)0.0127 (13)0.0023 (12)
C10A0.0740 (18)0.074 (2)0.0630 (16)0.0249 (15)0.0150 (14)0.0074 (14)
C11A0.0554 (14)0.0537 (16)0.0571 (14)0.0101 (12)0.0132 (11)0.0036 (11)
C12A0.0590 (17)0.084 (2)0.091 (2)0.0025 (15)0.0206 (15)0.0202 (16)
C13A0.0577 (15)0.0531 (16)0.0561 (14)0.0139 (12)0.0183 (12)0.0016 (11)
C14A0.0516 (13)0.0595 (16)0.0462 (12)0.0106 (12)0.0218 (11)0.0069 (11)
C15A0.0811 (19)0.082 (2)0.0561 (15)0.0279 (16)0.0084 (13)0.0089 (13)
C16A0.0488 (13)0.0580 (15)0.0504 (13)0.0116 (11)0.0227 (11)0.0065 (11)
C17A0.0737 (17)0.074 (2)0.0569 (15)0.0262 (15)0.0158 (13)0.0056 (13)
C18A0.092 (2)0.086 (2)0.0727 (18)0.0438 (19)0.0161 (16)0.0094 (16)
C19A0.0778 (19)0.071 (2)0.0837 (19)0.0318 (16)0.0378 (16)0.0095 (15)
C20A0.0568 (15)0.0605 (17)0.0660 (15)0.0094 (13)0.0343 (13)0.0024 (12)
C21A0.0507 (13)0.0659 (17)0.0537 (13)0.0143 (12)0.0252 (11)0.0047 (12)
O1B0.0702 (11)0.0641 (12)0.0644 (10)0.0252 (10)0.0161 (9)0.0083 (9)
O2B0.205 (3)0.142 (3)0.0968 (18)0.106 (2)0.005 (2)0.0231 (17)
O3B0.201 (3)0.116 (2)0.168 (3)0.101 (2)0.038 (2)0.0118 (19)
N1B0.0633 (12)0.0630 (14)0.0426 (10)0.0180 (11)0.0169 (9)0.0075 (9)
N2B0.0570 (11)0.0577 (13)0.0471 (11)0.0141 (10)0.0210 (9)0.0034 (9)
N3B0.103 (2)0.074 (2)0.104 (2)0.0396 (17)0.0369 (18)0.0064 (17)
C1B0.135 (3)0.093 (3)0.117 (3)0.038 (2)0.083 (2)0.017 (2)
C2B0.118 (3)0.118 (3)0.0690 (19)0.022 (2)0.033 (2)0.0003 (18)
C3B0.100 (2)0.0682 (19)0.0791 (19)0.0332 (17)0.0504 (17)0.0104 (15)
C4B0.101 (2)0.094 (2)0.090 (2)0.0529 (19)0.0547 (18)0.0229 (17)
C5B0.0766 (17)0.072 (2)0.0564 (14)0.0358 (16)0.0289 (13)0.0105 (13)
C6B0.0628 (16)0.0652 (18)0.0709 (16)0.0157 (13)0.0292 (13)0.0028 (13)
C7B0.0598 (15)0.0557 (17)0.0620 (15)0.0143 (13)0.0228 (12)0.0090 (12)
C8B0.0555 (14)0.0536 (15)0.0383 (11)0.0134 (12)0.0121 (10)0.0031 (10)
C9B0.0882 (19)0.0559 (17)0.0632 (15)0.0196 (14)0.0366 (14)0.0018 (12)
C10B0.107 (2)0.065 (2)0.0667 (16)0.0440 (18)0.0423 (16)0.0071 (13)
C11B0.0551 (14)0.0557 (16)0.0476 (12)0.0094 (12)0.0174 (11)0.0043 (11)
C12B0.0565 (15)0.099 (2)0.0598 (15)0.0178 (15)0.0123 (13)0.0072 (14)
C13B0.0503 (13)0.0615 (17)0.0483 (13)0.0097 (12)0.0214 (11)0.0016 (11)
C14B0.0555 (14)0.0595 (16)0.0464 (13)0.0051 (12)0.0220 (11)0.0082 (11)
C15B0.089 (2)0.082 (2)0.0462 (13)0.0077 (16)0.0183 (13)0.0008 (13)
C16B0.0507 (13)0.0666 (18)0.0540 (14)0.0063 (12)0.0235 (11)0.0182 (12)
C17B0.0678 (18)0.088 (2)0.0623 (16)0.0152 (16)0.0208 (14)0.0247 (15)
C18B0.076 (2)0.104 (3)0.086 (2)0.034 (2)0.0236 (17)0.049 (2)
C19B0.081 (2)0.077 (2)0.111 (3)0.0325 (18)0.047 (2)0.042 (2)
C20B0.0647 (16)0.0629 (18)0.0821 (19)0.0182 (14)0.0341 (15)0.0219 (15)
C21B0.0592 (15)0.0637 (18)0.0622 (15)0.0196 (13)0.0221 (12)0.0158 (13)
Geometric parameters (Å, º) top
O1A—C13A1.228 (3)C12A—H12D0.9600
O2A—N3A1.226 (4)C15A—H15A0.9600
O3A—N3A1.224 (4)C15A—H15C0.9600
O1B—C13B1.222 (3)C15A—H15B0.9600
O2B—N3B1.194 (4)C17A—H17A0.9300
O3B—N3B1.195 (4)C18A—H18A0.9300
N1A—N2A1.374 (3)C19A—H19A0.9300
N1A—C13A1.351 (3)C21A—H21A0.9300
N2A—C14A1.282 (3)C1B—C3B1.519 (6)
N3A—C20A1.477 (4)C2B—C3B1.512 (5)
N1A—H1A0.8600C3B—C4B1.522 (4)
N1B—C13B1.359 (3)C4B—C5B1.513 (5)
N1B—N2B1.371 (3)C5B—C6B1.379 (4)
N2B—C14B1.281 (3)C5B—C10B1.383 (4)
N3B—C20B1.471 (4)C6B—C7B1.379 (4)
N1B—H1B0.8600C7B—C8B1.383 (4)
C1A—C3A1.483 (6)C8B—C11B1.517 (4)
C2A—C3A1.541 (6)C8B—C9B1.375 (4)
C3A—C4A1.500 (6)C9B—C10B1.380 (5)
C4A—C5A1.514 (4)C11B—C13B1.526 (3)
C5A—C10A1.384 (4)C11B—C12B1.534 (4)
C5A—C6A1.369 (5)C14B—C15B1.509 (3)
C6A—C7A1.380 (4)C14B—C16B1.481 (4)
C7A—C8A1.387 (4)C16B—C21B1.399 (4)
C8A—C11A1.516 (3)C16B—C17B1.396 (4)
C8A—C9A1.373 (4)C17B—C18B1.373 (5)
C9A—C10A1.384 (4)C18B—C19B1.363 (6)
C11A—C12A1.530 (4)C19B—C20B1.386 (5)
C11A—C13A1.518 (4)C20B—C21B1.362 (4)
C14A—C16A1.479 (4)C1B—H1B10.9600
C14A—C15A1.504 (3)C1B—H1B20.9600
C16A—C17A1.387 (4)C1B—H1B30.9600
C16A—C21A1.398 (3)C2B—H2B10.9600
C17A—C18A1.382 (5)C2B—H2B20.9600
C18A—C19A1.374 (4)C2B—H2B30.9600
C19A—C20A1.376 (4)C3B—H3B0.9800
C20A—C21A1.365 (4)C4B—H4B10.9700
C1A—H1A10.9600C4B—H4B20.9700
C1A—H1A30.9600C6B—H6B0.9300
C1A—H1A20.9600C7B—H7B0.9300
C2A—H2A20.9600C9B—H9B0.9300
C2A—H2A30.9600C10B—H10B0.9300
C2A—H2A10.9600C11B—H11B0.9800
C3A—H3A0.9800C12B—H12A0.9600
C4A—H4A20.9700C12B—H12B0.9600
C4A—H4A10.9700C12B—H12C0.9600
C6A—H6A0.9300C15B—H15D0.9600
C7A—H7A0.9300C15B—H15E0.9600
C9A—H9A0.9300C15B—H15F0.9600
C10A—H10A0.9300C17B—H17B0.9300
C11A—H11A0.9800C18B—H18B0.9300
C12A—H12F0.9600C19B—H19B0.9300
C12A—H12E0.9600C21B—H210.9300
N2A—N1A—C13A121.0 (2)C16A—C17A—H17A119.00
N1A—N2A—C14A118.38 (19)C19A—C18A—H18A120.00
O2A—N3A—O3A123.9 (3)C17A—C18A—H18A120.00
O2A—N3A—C20A117.8 (2)C18A—C19A—H19A121.00
O3A—N3A—C20A118.3 (2)C20A—C19A—H19A121.00
C13A—N1A—H1A119.00C20A—C21A—H21A120.00
N2A—N1A—H1A120.00C16A—C21A—H21A120.00
N2B—N1B—C13B120.56 (19)C1B—C3B—C4B112.1 (3)
N1B—N2B—C14B118.6 (2)C1B—C3B—C2B110.4 (3)
O2B—N3B—C20B119.3 (3)C2B—C3B—C4B112.2 (3)
O3B—N3B—C20B118.3 (3)C3B—C4B—C5B114.8 (3)
O2B—N3B—O3B122.5 (3)C6B—C5B—C10B116.4 (3)
C13B—N1B—H1B120.00C4B—C5B—C10B122.1 (3)
N2B—N1B—H1B120.00C4B—C5B—C6B121.6 (3)
C1A—C3A—C4A115.7 (4)C5B—C6B—C7B121.9 (3)
C1A—C3A—C2A111.7 (4)C6B—C7B—C8B121.4 (2)
C2A—C3A—C4A109.5 (3)C7B—C8B—C11B121.3 (2)
C3A—C4A—C5A115.1 (3)C7B—C8B—C9B117.0 (3)
C4A—C5A—C6A122.0 (3)C9B—C8B—C11B121.6 (2)
C6A—C5A—C10A116.2 (3)C8B—C9B—C10B121.4 (3)
C4A—C5A—C10A121.8 (3)C5B—C10B—C9B121.9 (3)
C5A—C6A—C7A122.6 (3)C8B—C11B—C12B110.17 (18)
C6A—C7A—C8A121.0 (3)C8B—C11B—C13B110.2 (2)
C7A—C8A—C9A116.7 (2)C12B—C11B—C13B110.4 (2)
C7A—C8A—C11A121.8 (2)O1B—C13B—N1B119.5 (2)
C9A—C8A—C11A121.5 (2)N1B—C13B—C11B117.8 (2)
C8A—C9A—C10A121.8 (2)O1B—C13B—C11B122.7 (2)
C5A—C10A—C9A121.7 (3)N2B—C14B—C16B114.5 (2)
C12A—C11A—C13A109.0 (2)C15B—C14B—C16B120.5 (2)
C8A—C11A—C13A110.1 (2)N2B—C14B—C15B125.0 (2)
C8A—C11A—C12A112.6 (2)C17B—C16B—C21B116.9 (3)
O1A—C13A—N1A119.5 (2)C14B—C16B—C17B123.1 (2)
N1A—C13A—C11A118.9 (2)C14B—C16B—C21B120.0 (2)
O1A—C13A—C11A121.6 (2)C16B—C17B—C18B121.8 (3)
C15A—C14A—C16A119.7 (2)C17B—C18B—C19B120.8 (3)
N2A—C14A—C15A124.7 (2)C18B—C19B—C20B118.0 (3)
N2A—C14A—C16A115.7 (2)N3B—C20B—C19B119.0 (3)
C14A—C16A—C21A120.4 (2)N3B—C20B—C21B118.7 (2)
C17A—C16A—C21A117.3 (2)C19B—C20B—C21B122.3 (3)
C14A—C16A—C17A122.3 (2)C16B—C21B—C20B120.2 (2)
C16A—C17A—C18A121.8 (2)C3B—C1B—H1B1109.00
C17A—C18A—C19A120.6 (3)C3B—C1B—H1B2109.00
C18A—C19A—C20A117.4 (3)C3B—C1B—H1B3109.00
C19A—C20A—C21A123.2 (2)H1B1—C1B—H1B2109.00
N3A—C20A—C21A118.8 (2)H1B1—C1B—H1B3110.00
N3A—C20A—C19A118.1 (2)H1B2—C1B—H1B3109.00
C16A—C21A—C20A119.7 (2)C3B—C2B—H2B1109.00
C3A—C1A—H1A1110.00C3B—C2B—H2B2109.00
C3A—C1A—H1A2109.00C3B—C2B—H2B3109.00
H1A1—C1A—H1A2109.00H2B1—C2B—H2B2109.00
H1A2—C1A—H1A3109.00H2B1—C2B—H2B3109.00
H1A1—C1A—H1A3110.00H2B2—C2B—H2B3110.00
C3A—C1A—H1A3109.00C1B—C3B—H3B107.00
H2A1—C2A—H2A3109.00C2B—C3B—H3B107.00
C3A—C2A—H2A1109.00C4B—C3B—H3B107.00
C3A—C2A—H2A2109.00C3B—C4B—H4B1108.00
C3A—C2A—H2A3109.00C3B—C4B—H4B2109.00
H2A1—C2A—H2A2110.00C5B—C4B—H4B1109.00
H2A2—C2A—H2A3109.00C5B—C4B—H4B2109.00
C4A—C3A—H3A106.00H4B1—C4B—H4B2108.00
C2A—C3A—H3A106.00C5B—C6B—H6B119.00
C1A—C3A—H3A106.00C7B—C6B—H6B119.00
C3A—C4A—H4A1108.00C6B—C7B—H7B119.00
C3A—C4A—H4A2109.00C8B—C7B—H7B119.00
C5A—C4A—H4A2109.00C8B—C9B—H9B119.00
H4A1—C4A—H4A2108.00C10B—C9B—H9B119.00
C5A—C4A—H4A1108.00C5B—C10B—H10B119.00
C5A—C6A—H6A119.00C9B—C10B—H10B119.00
C7A—C6A—H6A119.00C8B—C11B—H11B109.00
C8A—C7A—H7A119.00C12B—C11B—H11B109.00
C6A—C7A—H7A120.00C13B—C11B—H11B109.00
C10A—C9A—H9A119.00C11B—C12B—H12A109.00
C8A—C9A—H9A119.00C11B—C12B—H12B109.00
C9A—C10A—H10A119.00C11B—C12B—H12C109.00
C5A—C10A—H10A119.00H12A—C12B—H12B109.00
C13A—C11A—H11A108.00H12A—C12B—H12C110.00
C8A—C11A—H11A108.00H12B—C12B—H12C109.00
C12A—C11A—H11A108.00C14B—C15B—H15D109.00
H12D—C12A—H12F110.00C14B—C15B—H15E109.00
C11A—C12A—H12E109.00C14B—C15B—H15F109.00
H12D—C12A—H12E109.00H15D—C15B—H15E109.00
C11A—C12A—H12D109.00H15D—C15B—H15F109.00
H12E—C12A—H12F110.00H15E—C15B—H15F109.00
C11A—C12A—H12F109.00C16B—C17B—H17B119.00
H15A—C15A—H15C110.00C18B—C17B—H17B119.00
H15B—C15A—H15C109.00C17B—C18B—H18B120.00
C14A—C15A—H15B109.00C19B—C18B—H18B120.00
C14A—C15A—H15C110.00C18B—C19B—H19B121.00
C14A—C15A—H15A109.00C20B—C19B—H19B121.00
H15A—C15A—H15B109.00C16B—C21B—H21120.00
C18A—C17A—H17A119.00C20B—C21B—H21120.00
C13A—N1A—N2A—C14A172.6 (2)C21A—C16A—C17A—C18A2.2 (4)
N2A—N1A—C13A—O1A173.5 (2)C17A—C16A—C21A—C20A1.2 (4)
N2A—N1A—C13A—C11A8.1 (3)C14A—C16A—C21A—C20A178.7 (2)
N1A—N2A—C14A—C15A2.2 (4)C16A—C17A—C18A—C19A1.6 (5)
N1A—N2A—C14A—C16A178.7 (2)C17A—C18A—C19A—C20A0.0 (5)
O2A—N3A—C20A—C19A175.9 (3)C18A—C19A—C20A—N3A179.8 (3)
O2A—N3A—C20A—C21A4.8 (4)C18A—C19A—C20A—C21A1.0 (5)
O3A—N3A—C20A—C19A3.4 (4)C19A—C20A—C21A—C16A0.4 (4)
O3A—N3A—C20A—C21A175.9 (3)N3A—C20A—C21A—C16A179.6 (2)
N2B—N1B—C13B—C11B1.1 (4)C1B—C3B—C4B—C5B178.4 (3)
C13B—N1B—N2B—C14B178.8 (2)C2B—C3B—C4B—C5B56.8 (4)
N2B—N1B—C13B—O1B177.7 (2)C3B—C4B—C5B—C6B59.8 (4)
N1B—N2B—C14B—C15B1.9 (4)C3B—C4B—C5B—C10B118.8 (3)
N1B—N2B—C14B—C16B177.5 (2)C4B—C5B—C6B—C7B177.5 (2)
O2B—N3B—C20B—C21B2.0 (5)C10B—C5B—C6B—C7B1.2 (4)
O2B—N3B—C20B—C19B179.5 (4)C4B—C5B—C10B—C9B178.4 (3)
O3B—N3B—C20B—C21B179.1 (3)C6B—C5B—C10B—C9B0.3 (4)
O3B—N3B—C20B—C19B0.6 (5)C5B—C6B—C7B—C8B1.1 (4)
C2A—C3A—C4A—C5A170.2 (3)C6B—C7B—C8B—C9B0.0 (3)
C1A—C3A—C4A—C5A62.6 (4)C6B—C7B—C8B—C11B176.5 (2)
C3A—C4A—C5A—C6A92.9 (4)C7B—C8B—C9B—C10B0.9 (4)
C3A—C4A—C5A—C10A84.7 (4)C11B—C8B—C9B—C10B175.6 (2)
C4A—C5A—C6A—C7A177.8 (3)C7B—C8B—C11B—C12B80.2 (3)
C10A—C5A—C6A—C7A0.1 (5)C7B—C8B—C11B—C13B41.9 (3)
C4A—C5A—C10A—C9A178.6 (3)C9B—C8B—C11B—C12B96.2 (3)
C6A—C5A—C10A—C9A0.9 (5)C9B—C8B—C11B—C13B141.7 (2)
C5A—C6A—C7A—C8A0.3 (5)C8B—C9B—C10B—C5B0.8 (4)
C6A—C7A—C8A—C9A0.2 (4)C8B—C11B—C13B—O1B105.5 (3)
C6A—C7A—C8A—C11A179.4 (3)C8B—C11B—C13B—N1B73.2 (3)
C7A—C8A—C9A—C10A1.0 (4)C12B—C11B—C13B—O1B16.4 (3)
C7A—C8A—C11A—C13A64.8 (3)C12B—C11B—C13B—N1B164.9 (2)
C9A—C8A—C11A—C12A122.2 (3)N2B—C14B—C16B—C17B178.0 (3)
C9A—C8A—C11A—C13A115.9 (3)N2B—C14B—C16B—C21B0.3 (4)
C11A—C8A—C9A—C10A179.8 (2)C15B—C14B—C16B—C17B1.3 (4)
C7A—C8A—C11A—C12A57.0 (3)C15B—C14B—C16B—C21B179.6 (3)
C8A—C9A—C10A—C5A1.4 (4)C14B—C16B—C17B—C18B178.1 (3)
C12A—C11A—C13A—O1A37.8 (3)C21B—C16B—C17B—C18B0.3 (5)
C8A—C11A—C13A—O1A86.1 (3)C14B—C16B—C21B—C20B178.7 (2)
C8A—C11A—C13A—N1A95.5 (3)C17B—C16B—C21B—C20B0.4 (4)
C12A—C11A—C13A—N1A140.6 (2)C16B—C17B—C18B—C19B0.4 (6)
N2A—C14A—C16A—C21A4.6 (4)C17B—C18B—C19B—C20B0.2 (6)
C15A—C14A—C16A—C17A3.9 (4)C18B—C19B—C20B—N3B179.3 (3)
N2A—C14A—C16A—C17A175.3 (2)C18B—C19B—C20B—C21B0.9 (5)
C15A—C14A—C16A—C21A176.2 (3)N3B—C20B—C21B—C16B179.4 (3)
C14A—C16A—C17A—C18A177.7 (3)C19B—C20B—C21B—C16B0.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Bi0.862.142.977 (3)165
N1B—H1B···O1Aii0.862.152.919 (3)149
C11A—H11A···N2A0.982.412.803 (4)103
C15A—H15C···O1Bi0.962.413.252 (4)147
C15A—H15C···N1A0.962.412.791 (4)103
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Bi0.862.142.977 (3)165
N1B—H1B···O1Aii0.862.152.919 (3)149
C15A—H15C···O1Bi0.962.413.252 (4)147
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

Acknowledgements

SMK thanks UGC-BRS and the University of Mysore for awarding a fellowship. MPS acknowledges the University Grants Commission, New Delhi, India.

References

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