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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2013 Jul 27;69(Pt 8):o1333. doi: 10.1107/S1600536813019892

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

B C Manjunath a, S Madan Kumar a, A C Vinayaka b, S Jayasheelan c, M P Sadashiva b, N K Lokanath a,*
PMCID: PMC3793817  PMID: 24109404

Abstract

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). 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 R 2 2(8) ring motifs. In addition, π–π 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). 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).graphic file with name e-69-o1333-scheme1.jpg

Experimental  

Crystal data  

  • C21H25N3O3

  • M r = 367.44

  • Triclinic, Inline graphic

  • 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)

  • R int = 0.039

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.068

  • wR(F 2) = 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

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019892/gk2579sup1.cif

e-69-o1333-sup1.cif (45.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019892/gk2579Isup2.hkl

e-69-o1333-Isup2.hkl (432.5KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536813019892/gk2579Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O1B i 0.86 2.14 2.977 (3) 165
N1B—H1B⋯O1A ii 0.86 2.15 2.919 (3) 149
C15A—H15C⋯O1B i 0.96 2.41 3.252 (4) 147

Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

Molecule A of the title compound with displacement ellipsoids shown at the 50% probability level.

Fig. 2.

Fig. 2.

Molecule B of the title compound with displacement ellipsoids shown at the 50% probability level.

Fig. 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.

Crystal data

C21H25N3O3 Z = 4
Mr = 367.44 F(000) = 784
Triclinic, P1 Dx = 1.202 Mg m3
Hall symbol: -P 1 Melting point: 442 K
a = 12.201 (5) Å Mo Kα radiation, λ = 0.71073 Å
b = 13.429 (5) Å Cell parameters from 8844 reflections
c = 13.932 (5) Å θ = 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) Å3 0.23 × 0.22 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer 4673 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.039
Graphite monochromator θmax = 27.1°, θmin = 1.6°
Detector resolution: 16.0839 pixels mm-1 h = −15→15
ω scans k = −17→17
21740 measured reflections l = −17→17
8844 independent reflections

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193 H-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 parameters Δρmax = 0.19 e Å3
0 restraints Δρmin = −0.16 e Å3

Special details

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)

x y z Uiso*/Ueq
O1A 0.84024 (16) −0.14913 (15) 0.55714 (13) 0.0761 (7)
O2A 0.7121 (2) 0.3312 (2) 0.70085 (17) 0.1031 (10)
O3A 0.6171 (2) 0.44110 (17) 0.63494 (17) 0.0948 (9)
N1A 0.71527 (17) −0.05635 (16) 0.48633 (14) 0.0577 (7)
N2A 0.67981 (18) 0.03078 (15) 0.49209 (14) 0.0551 (7)
N3A 0.6410 (2) 0.3595 (2) 0.6291 (2) 0.0756 (10)
C1A 0.6003 (4) −0.1837 (3) 0.9456 (3) 0.1231 (18)
C2A 0.6171 (4) −0.0619 (4) 1.0906 (3) 0.134 (2)
C3A 0.6444 (4) −0.0725 (3) 0.9916 (3) 0.1029 (16)
C4A 0.7774 (3) −0.0140 (3) 1.0121 (2) 0.1044 (15)
C5A 0.8123 (3) −0.0023 (3) 0.9175 (2) 0.0768 (10)
C6A 0.8563 (3) −0.0728 (3) 0.8837 (2) 0.0910 (15)
C7A 0.8846 (3) −0.0651 (2) 0.7957 (2) 0.0797 (11)
C8A 0.8700 (2) 0.0160 (2) 0.73670 (17) 0.0563 (8)
C9A 0.8267 (2) 0.0874 (2) 0.77044 (19) 0.0639 (9)
C10A 0.7972 (2) 0.0782 (2) 0.8581 (2) 0.0729 (10)
C11A 0.9017 (2) 0.0263 (2) 0.64037 (18) 0.0592 (8)
C12A 1.0355 (2) 0.0331 (2) 0.6613 (2) 0.0848 (11)
C13A 0.8170 (2) −0.0664 (2) 0.55925 (18) 0.0572 (9)
C14A 0.5906 (2) 0.04170 (19) 0.41559 (17) 0.0530 (8)
C15A 0.5237 (3) −0.0325 (2) 0.31726 (19) 0.0773 (10)
C16A 0.5552 (2) 0.13587 (19) 0.42770 (17) 0.0524 (8)
C17A 0.4665 (2) 0.1624 (2) 0.34890 (19) 0.0698 (10)
C18A 0.4373 (3) 0.2526 (3) 0.3600 (2) 0.0838 (11)
C19A 0.4939 (3) 0.3181 (2) 0.4514 (2) 0.0733 (11)
C20A 0.5797 (2) 0.2901 (2) 0.53021 (19) 0.0600 (9)
C21A 0.6115 (2) 0.2023 (2) 0.52082 (17) 0.0561 (8)
O1B 0.60116 (16) 0.75492 (14) 0.32931 (12) 0.0678 (6)
O2B 0.7193 (3) 0.2616 (2) 0.2322 (2) 0.1500 (15)
O3B 0.8201 (3) 0.1626 (2) 0.3011 (2) 0.1580 (16)
N1B 0.70320 (18) 0.65361 (16) 0.42081 (14) 0.0575 (7)
N2B 0.73709 (17) 0.56469 (16) 0.42424 (14) 0.0544 (7)
N3B 0.7882 (3) 0.2379 (2) 0.3055 (2) 0.0912 (12)
C1B 1.0431 (3) 0.6854 (3) −0.0762 (3) 0.1043 (17)
C2B 0.8173 (3) 0.6347 (3) −0.1156 (2) 0.1057 (15)
C3B 0.9435 (3) 0.6789 (2) −0.0323 (2) 0.0760 (11)
C4B 0.9575 (3) 0.6178 (3) 0.0603 (2) 0.0843 (12)
C5B 0.8631 (3) 0.6109 (2) 0.10965 (18) 0.0642 (10)
C6B 0.8514 (2) 0.6997 (2) 0.14981 (19) 0.0661 (10)
C7B 0.7625 (2) 0.6943 (2) 0.19134 (17) 0.0601 (9)
C8B 0.6818 (2) 0.59888 (19) 0.19621 (15) 0.0515 (8)
C9B 0.6943 (3) 0.5099 (2) 0.15785 (18) 0.0674 (10)
C10B 0.7823 (3) 0.5158 (2) 0.11506 (19) 0.0727 (11)
C11B 0.5795 (2) 0.59323 (19) 0.23640 (16) 0.0552 (8)
C12B 0.4704 (2) 0.6125 (2) 0.15221 (19) 0.0760 (10)
C13B 0.6271 (2) 0.6736 (2) 0.33137 (17) 0.0544 (8)
C14B 0.8072 (2) 0.5478 (2) 0.51048 (17) 0.0560 (8)
C15B 0.8537 (3) 0.6172 (2) 0.61121 (18) 0.0788 (10)
C16B 0.8429 (2) 0.4523 (2) 0.50529 (18) 0.0587 (9)
C17B 0.9217 (2) 0.4223 (3) 0.5904 (2) 0.0757 (10)
C18B 0.9561 (3) 0.3350 (3) 0.5827 (3) 0.0888 (14)
C19B 0.9135 (3) 0.2737 (3) 0.4908 (3) 0.0844 (14)
C20B 0.8343 (2) 0.3021 (2) 0.4058 (2) 0.0683 (10)
C21B 0.7998 (2) 0.3889 (2) 0.41132 (19) 0.0616 (9)
H1A 0.67210 −0.10530 0.43560 0.0690*
H4A1 0.82740 −0.05020 1.05870 0.1250*
H3A 0.59630 −0.03620 0.94160 0.1230*
H4A2 0.79750 0.05550 1.04680 0.1250*
H6A 0.86760 −0.12810 0.92150 0.1090*
H7A 0.91390 −0.11510 0.77560 0.0960*
H9A 0.81680 0.14350 0.73340 0.0770*
H10A 0.76650 0.12740 0.87770 0.0880*
H1A1 0.61870 −0.18750 0.88430 0.1850*
H11A 0.88910 0.09070 0.61300 0.0710*
H1A2 0.51290 −0.21200 0.92870 0.1850*
H12D 1.04760 −0.03190 0.68230 0.1270*
H12E 1.08950 0.08940 0.71510 0.1270*
H12F 1.05330 0.04610 0.59980 0.1270*
H1A3 0.64070 −0.22360 0.99420 0.1850*
H2A1 0.66670 −0.09230 1.14350 0.2010*
H2A2 0.53160 −0.09780 1.07700 0.2010*
H15A 0.51060 0.00710 0.25970 0.1160*
H15B 0.44560 −0.07640 0.31740 0.1160*
H15C 0.57200 −0.07560 0.31190 0.1160*
H2A3 0.63620 0.01110 1.11300 0.2010*
H17A 0.42550 0.11830 0.28690 0.0840*
H18A 0.37880 0.26920 0.30510 0.1010*
H19A 0.47490 0.37890 0.45980 0.0880*
H21A 0.67030 0.18670 0.57610 0.0670*
H4B1 0.95220 0.54710 0.03880 0.1010*
H1B 0.73030 0.69710 0.47570 0.0690*
H4B2 1.03900 0.65070 0.11170 0.1010*
H3B 0.95290 0.75090 −0.00840 0.0910*
H2B1 0.81100 0.67760 −0.17080 0.1590*
H2B2 0.75540 0.63420 −0.08760 0.1590*
H6B 0.90500 0.76520 0.14880 0.0790*
H2B3 0.80540 0.56430 −0.14140 0.1590*
H7B 0.75670 0.75610 0.21660 0.0720*
H1B1 1.02760 0.61810 −0.11160 0.1560*
H1B2 1.12200 0.70520 −0.02120 0.1560*
H9B 0.64230 0.44430 0.16080 0.0810*
H1B3 1.04270 0.73700 −0.12350 0.1560*
H10B 0.78740 0.45400 0.08910 0.0880*
H11B 0.55160 0.52280 0.25590 0.0660*
H12A 0.49630 0.68180 0.13330 0.1140*
H12B 0.40510 0.60630 0.17770 0.1140*
H12C 0.44150 0.56140 0.09300 0.1140*
H15D 0.90770 0.68430 0.60720 0.1180*
H15E 0.89770 0.58480 0.66580 0.1180*
H15F 0.78510 0.62670 0.62470 0.1180*
H17B 0.95180 0.46260 0.65410 0.0910*
H18B 1.00910 0.31750 0.64090 0.1070*
H19B 0.93680 0.21460 0.48530 0.1010*
H21 0.74740 0.40610 0.35250 0.0740*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1A 0.0714 (12) 0.0606 (12) 0.0770 (12) 0.0225 (10) 0.0029 (9) −0.0123 (9)
O2A 0.0921 (16) 0.131 (2) 0.0766 (14) 0.0391 (15) 0.0172 (12) −0.0294 (13)
O3A 0.1093 (17) 0.0687 (15) 0.1118 (16) 0.0122 (13) 0.0610 (14) −0.0153 (12)
N1A 0.0541 (12) 0.0579 (13) 0.0511 (11) 0.0133 (10) 0.0112 (9) −0.0054 (9)
N2A 0.0577 (12) 0.0543 (13) 0.0531 (11) 0.0167 (10) 0.0210 (10) 0.0019 (9)
N3A 0.0684 (16) 0.0825 (19) 0.0784 (17) 0.0090 (14) 0.0431 (14) −0.0097 (14)
C1A 0.120 (3) 0.147 (4) 0.077 (2) 0.010 (3) 0.033 (2) 0.014 (2)
C2A 0.175 (4) 0.166 (4) 0.109 (3) 0.078 (3) 0.090 (3) 0.040 (3)
C3A 0.119 (3) 0.125 (3) 0.084 (2) 0.053 (3) 0.048 (2) 0.029 (2)
C4A 0.112 (3) 0.131 (3) 0.0567 (17) 0.028 (2) 0.0239 (18) 0.0022 (18)
C5A 0.0759 (18) 0.088 (2) 0.0513 (15) 0.0187 (17) 0.0113 (13) 0.0007 (15)
C6A 0.112 (3) 0.094 (3) 0.0698 (19) 0.046 (2) 0.0249 (18) 0.0283 (17)
C7A 0.096 (2) 0.078 (2) 0.0737 (18) 0.0449 (18) 0.0266 (16) 0.0120 (16)
C8A 0.0483 (13) 0.0552 (16) 0.0519 (13) 0.0136 (12) 0.0047 (11) −0.0004 (11)
C9A 0.0660 (16) 0.0578 (17) 0.0594 (15) 0.0199 (13) 0.0127 (13) 0.0023 (12)
C10A 0.0740 (18) 0.074 (2) 0.0630 (16) 0.0249 (15) 0.0150 (14) −0.0074 (14)
C11A 0.0554 (14) 0.0537 (16) 0.0571 (14) 0.0101 (12) 0.0132 (11) −0.0036 (11)
C12A 0.0590 (17) 0.084 (2) 0.091 (2) 0.0025 (15) 0.0206 (15) −0.0202 (16)
C13A 0.0577 (15) 0.0531 (16) 0.0561 (14) 0.0139 (12) 0.0183 (12) −0.0016 (11)
C14A 0.0516 (13) 0.0595 (16) 0.0462 (12) 0.0106 (12) 0.0218 (11) 0.0069 (11)
C15A 0.0811 (19) 0.082 (2) 0.0561 (15) 0.0279 (16) 0.0084 (13) −0.0089 (13)
C16A 0.0488 (13) 0.0580 (15) 0.0504 (13) 0.0116 (11) 0.0227 (11) 0.0065 (11)
C17A 0.0737 (17) 0.074 (2) 0.0569 (15) 0.0262 (15) 0.0158 (13) 0.0056 (13)
C18A 0.092 (2) 0.086 (2) 0.0727 (18) 0.0438 (19) 0.0161 (16) 0.0094 (16)
C19A 0.0778 (19) 0.071 (2) 0.0837 (19) 0.0318 (16) 0.0378 (16) 0.0095 (15)
C20A 0.0568 (15) 0.0605 (17) 0.0660 (15) 0.0094 (13) 0.0343 (13) −0.0024 (12)
C21A 0.0507 (13) 0.0659 (17) 0.0537 (13) 0.0143 (12) 0.0252 (11) 0.0047 (12)
O1B 0.0702 (11) 0.0641 (12) 0.0644 (10) 0.0252 (10) 0.0161 (9) −0.0083 (9)
O2B 0.205 (3) 0.142 (3) 0.0968 (18) 0.106 (2) 0.005 (2) −0.0231 (17)
O3B 0.201 (3) 0.116 (2) 0.168 (3) 0.101 (2) 0.038 (2) −0.0118 (19)
N1B 0.0633 (12) 0.0630 (14) 0.0426 (10) 0.0180 (11) 0.0169 (9) −0.0075 (9)
N2B 0.0570 (11) 0.0577 (13) 0.0471 (11) 0.0141 (10) 0.0210 (9) 0.0034 (9)
N3B 0.103 (2) 0.074 (2) 0.104 (2) 0.0396 (17) 0.0369 (18) 0.0064 (17)
C1B 0.135 (3) 0.093 (3) 0.117 (3) 0.038 (2) 0.083 (2) 0.017 (2)
C2B 0.118 (3) 0.118 (3) 0.0690 (19) 0.022 (2) 0.033 (2) 0.0003 (18)
C3B 0.100 (2) 0.0682 (19) 0.0791 (19) 0.0332 (17) 0.0504 (17) 0.0104 (15)
C4B 0.101 (2) 0.094 (2) 0.090 (2) 0.0529 (19) 0.0547 (18) 0.0229 (17)
C5B 0.0766 (17) 0.072 (2) 0.0564 (14) 0.0358 (16) 0.0289 (13) 0.0105 (13)
C6B 0.0628 (16) 0.0652 (18) 0.0709 (16) 0.0157 (13) 0.0292 (13) 0.0028 (13)
C7B 0.0598 (15) 0.0557 (17) 0.0620 (15) 0.0143 (13) 0.0228 (12) −0.0090 (12)
C8B 0.0555 (14) 0.0536 (15) 0.0383 (11) 0.0134 (12) 0.0121 (10) −0.0031 (10)
C9B 0.0882 (19) 0.0559 (17) 0.0632 (15) 0.0196 (14) 0.0366 (14) 0.0018 (12)
C10B 0.107 (2) 0.065 (2) 0.0667 (16) 0.0440 (18) 0.0423 (16) 0.0071 (13)
C11B 0.0551 (14) 0.0557 (16) 0.0476 (12) 0.0094 (12) 0.0174 (11) −0.0043 (11)
C12B 0.0565 (15) 0.099 (2) 0.0598 (15) 0.0178 (15) 0.0123 (13) −0.0072 (14)
C13B 0.0503 (13) 0.0615 (17) 0.0483 (13) 0.0097 (12) 0.0214 (11) −0.0016 (11)
C14B 0.0555 (14) 0.0595 (16) 0.0464 (13) 0.0051 (12) 0.0220 (11) 0.0082 (11)
C15B 0.089 (2) 0.082 (2) 0.0462 (13) 0.0077 (16) 0.0183 (13) 0.0008 (13)
C16B 0.0507 (13) 0.0666 (18) 0.0540 (14) 0.0063 (12) 0.0235 (11) 0.0182 (12)
C17B 0.0678 (18) 0.088 (2) 0.0623 (16) 0.0152 (16) 0.0208 (14) 0.0247 (15)
C18B 0.076 (2) 0.104 (3) 0.086 (2) 0.034 (2) 0.0236 (17) 0.049 (2)
C19B 0.081 (2) 0.077 (2) 0.111 (3) 0.0325 (18) 0.047 (2) 0.042 (2)
C20B 0.0647 (16) 0.0629 (18) 0.0821 (19) 0.0182 (14) 0.0341 (15) 0.0219 (15)
C21B 0.0592 (15) 0.0637 (18) 0.0622 (15) 0.0196 (13) 0.0221 (12) 0.0158 (13)

Geometric parameters (Å, º)

O1A—C13A 1.228 (3) C12A—H12D 0.9600
O2A—N3A 1.226 (4) C15A—H15A 0.9600
O3A—N3A 1.224 (4) C15A—H15C 0.9600
O1B—C13B 1.222 (3) C15A—H15B 0.9600
O2B—N3B 1.194 (4) C17A—H17A 0.9300
O3B—N3B 1.195 (4) C18A—H18A 0.9300
N1A—N2A 1.374 (3) C19A—H19A 0.9300
N1A—C13A 1.351 (3) C21A—H21A 0.9300
N2A—C14A 1.282 (3) C1B—C3B 1.519 (6)
N3A—C20A 1.477 (4) C2B—C3B 1.512 (5)
N1A—H1A 0.8600 C3B—C4B 1.522 (4)
N1B—C13B 1.359 (3) C4B—C5B 1.513 (5)
N1B—N2B 1.371 (3) C5B—C6B 1.379 (4)
N2B—C14B 1.281 (3) C5B—C10B 1.383 (4)
N3B—C20B 1.471 (4) C6B—C7B 1.379 (4)
N1B—H1B 0.8600 C7B—C8B 1.383 (4)
C1A—C3A 1.483 (6) C8B—C11B 1.517 (4)
C2A—C3A 1.541 (6) C8B—C9B 1.375 (4)
C3A—C4A 1.500 (6) C9B—C10B 1.380 (5)
C4A—C5A 1.514 (4) C11B—C13B 1.526 (3)
C5A—C10A 1.384 (4) C11B—C12B 1.534 (4)
C5A—C6A 1.369 (5) C14B—C15B 1.509 (3)
C6A—C7A 1.380 (4) C14B—C16B 1.481 (4)
C7A—C8A 1.387 (4) C16B—C21B 1.399 (4)
C8A—C11A 1.516 (3) C16B—C17B 1.396 (4)
C8A—C9A 1.373 (4) C17B—C18B 1.373 (5)
C9A—C10A 1.384 (4) C18B—C19B 1.363 (6)
C11A—C12A 1.530 (4) C19B—C20B 1.386 (5)
C11A—C13A 1.518 (4) C20B—C21B 1.362 (4)
C14A—C16A 1.479 (4) C1B—H1B1 0.9600
C14A—C15A 1.504 (3) C1B—H1B2 0.9600
C16A—C17A 1.387 (4) C1B—H1B3 0.9600
C16A—C21A 1.398 (3) C2B—H2B1 0.9600
C17A—C18A 1.382 (5) C2B—H2B2 0.9600
C18A—C19A 1.374 (4) C2B—H2B3 0.9600
C19A—C20A 1.376 (4) C3B—H3B 0.9800
C20A—C21A 1.365 (4) C4B—H4B1 0.9700
C1A—H1A1 0.9600 C4B—H4B2 0.9700
C1A—H1A3 0.9600 C6B—H6B 0.9300
C1A—H1A2 0.9600 C7B—H7B 0.9300
C2A—H2A2 0.9600 C9B—H9B 0.9300
C2A—H2A3 0.9600 C10B—H10B 0.9300
C2A—H2A1 0.9600 C11B—H11B 0.9800
C3A—H3A 0.9800 C12B—H12A 0.9600
C4A—H4A2 0.9700 C12B—H12B 0.9600
C4A—H4A1 0.9700 C12B—H12C 0.9600
C6A—H6A 0.9300 C15B—H15D 0.9600
C7A—H7A 0.9300 C15B—H15E 0.9600
C9A—H9A 0.9300 C15B—H15F 0.9600
C10A—H10A 0.9300 C17B—H17B 0.9300
C11A—H11A 0.9800 C18B—H18B 0.9300
C12A—H12F 0.9600 C19B—H19B 0.9300
C12A—H12E 0.9600 C21B—H21 0.9300
N2A—N1A—C13A 121.0 (2) C16A—C17A—H17A 119.00
N1A—N2A—C14A 118.38 (19) C19A—C18A—H18A 120.00
O2A—N3A—O3A 123.9 (3) C17A—C18A—H18A 120.00
O2A—N3A—C20A 117.8 (2) C18A—C19A—H19A 121.00
O3A—N3A—C20A 118.3 (2) C20A—C19A—H19A 121.00
C13A—N1A—H1A 119.00 C20A—C21A—H21A 120.00
N2A—N1A—H1A 120.00 C16A—C21A—H21A 120.00
N2B—N1B—C13B 120.56 (19) C1B—C3B—C4B 112.1 (3)
N1B—N2B—C14B 118.6 (2) C1B—C3B—C2B 110.4 (3)
O2B—N3B—C20B 119.3 (3) C2B—C3B—C4B 112.2 (3)
O3B—N3B—C20B 118.3 (3) C3B—C4B—C5B 114.8 (3)
O2B—N3B—O3B 122.5 (3) C6B—C5B—C10B 116.4 (3)
C13B—N1B—H1B 120.00 C4B—C5B—C10B 122.1 (3)
N2B—N1B—H1B 120.00 C4B—C5B—C6B 121.6 (3)
C1A—C3A—C4A 115.7 (4) C5B—C6B—C7B 121.9 (3)
C1A—C3A—C2A 111.7 (4) C6B—C7B—C8B 121.4 (2)
C2A—C3A—C4A 109.5 (3) C7B—C8B—C11B 121.3 (2)
C3A—C4A—C5A 115.1 (3) C7B—C8B—C9B 117.0 (3)
C4A—C5A—C6A 122.0 (3) C9B—C8B—C11B 121.6 (2)
C6A—C5A—C10A 116.2 (3) C8B—C9B—C10B 121.4 (3)
C4A—C5A—C10A 121.8 (3) C5B—C10B—C9B 121.9 (3)
C5A—C6A—C7A 122.6 (3) C8B—C11B—C12B 110.17 (18)
C6A—C7A—C8A 121.0 (3) C8B—C11B—C13B 110.2 (2)
C7A—C8A—C9A 116.7 (2) C12B—C11B—C13B 110.4 (2)
C7A—C8A—C11A 121.8 (2) O1B—C13B—N1B 119.5 (2)
C9A—C8A—C11A 121.5 (2) N1B—C13B—C11B 117.8 (2)
C8A—C9A—C10A 121.8 (2) O1B—C13B—C11B 122.7 (2)
C5A—C10A—C9A 121.7 (3) N2B—C14B—C16B 114.5 (2)
C12A—C11A—C13A 109.0 (2) C15B—C14B—C16B 120.5 (2)
C8A—C11A—C13A 110.1 (2) N2B—C14B—C15B 125.0 (2)
C8A—C11A—C12A 112.6 (2) C17B—C16B—C21B 116.9 (3)
O1A—C13A—N1A 119.5 (2) C14B—C16B—C17B 123.1 (2)
N1A—C13A—C11A 118.9 (2) C14B—C16B—C21B 120.0 (2)
O1A—C13A—C11A 121.6 (2) C16B—C17B—C18B 121.8 (3)
C15A—C14A—C16A 119.7 (2) C17B—C18B—C19B 120.8 (3)
N2A—C14A—C15A 124.7 (2) C18B—C19B—C20B 118.0 (3)
N2A—C14A—C16A 115.7 (2) N3B—C20B—C19B 119.0 (3)
C14A—C16A—C21A 120.4 (2) N3B—C20B—C21B 118.7 (2)
C17A—C16A—C21A 117.3 (2) C19B—C20B—C21B 122.3 (3)
C14A—C16A—C17A 122.3 (2) C16B—C21B—C20B 120.2 (2)
C16A—C17A—C18A 121.8 (2) C3B—C1B—H1B1 109.00
C17A—C18A—C19A 120.6 (3) C3B—C1B—H1B2 109.00
C18A—C19A—C20A 117.4 (3) C3B—C1B—H1B3 109.00
C19A—C20A—C21A 123.2 (2) H1B1—C1B—H1B2 109.00
N3A—C20A—C21A 118.8 (2) H1B1—C1B—H1B3 110.00
N3A—C20A—C19A 118.1 (2) H1B2—C1B—H1B3 109.00
C16A—C21A—C20A 119.7 (2) C3B—C2B—H2B1 109.00
C3A—C1A—H1A1 110.00 C3B—C2B—H2B2 109.00
C3A—C1A—H1A2 109.00 C3B—C2B—H2B3 109.00
H1A1—C1A—H1A2 109.00 H2B1—C2B—H2B2 109.00
H1A2—C1A—H1A3 109.00 H2B1—C2B—H2B3 109.00
H1A1—C1A—H1A3 110.00 H2B2—C2B—H2B3 110.00
C3A—C1A—H1A3 109.00 C1B—C3B—H3B 107.00
H2A1—C2A—H2A3 109.00 C2B—C3B—H3B 107.00
C3A—C2A—H2A1 109.00 C4B—C3B—H3B 107.00
C3A—C2A—H2A2 109.00 C3B—C4B—H4B1 108.00
C3A—C2A—H2A3 109.00 C3B—C4B—H4B2 109.00
H2A1—C2A—H2A2 110.00 C5B—C4B—H4B1 109.00
H2A2—C2A—H2A3 109.00 C5B—C4B—H4B2 109.00
C4A—C3A—H3A 106.00 H4B1—C4B—H4B2 108.00
C2A—C3A—H3A 106.00 C5B—C6B—H6B 119.00
C1A—C3A—H3A 106.00 C7B—C6B—H6B 119.00
C3A—C4A—H4A1 108.00 C6B—C7B—H7B 119.00
C3A—C4A—H4A2 109.00 C8B—C7B—H7B 119.00
C5A—C4A—H4A2 109.00 C8B—C9B—H9B 119.00
H4A1—C4A—H4A2 108.00 C10B—C9B—H9B 119.00
C5A—C4A—H4A1 108.00 C5B—C10B—H10B 119.00
C5A—C6A—H6A 119.00 C9B—C10B—H10B 119.00
C7A—C6A—H6A 119.00 C8B—C11B—H11B 109.00
C8A—C7A—H7A 119.00 C12B—C11B—H11B 109.00
C6A—C7A—H7A 120.00 C13B—C11B—H11B 109.00
C10A—C9A—H9A 119.00 C11B—C12B—H12A 109.00
C8A—C9A—H9A 119.00 C11B—C12B—H12B 109.00
C9A—C10A—H10A 119.00 C11B—C12B—H12C 109.00
C5A—C10A—H10A 119.00 H12A—C12B—H12B 109.00
C13A—C11A—H11A 108.00 H12A—C12B—H12C 110.00
C8A—C11A—H11A 108.00 H12B—C12B—H12C 109.00
C12A—C11A—H11A 108.00 C14B—C15B—H15D 109.00
H12D—C12A—H12F 110.00 C14B—C15B—H15E 109.00
C11A—C12A—H12E 109.00 C14B—C15B—H15F 109.00
H12D—C12A—H12E 109.00 H15D—C15B—H15E 109.00
C11A—C12A—H12D 109.00 H15D—C15B—H15F 109.00
H12E—C12A—H12F 110.00 H15E—C15B—H15F 109.00
C11A—C12A—H12F 109.00 C16B—C17B—H17B 119.00
H15A—C15A—H15C 110.00 C18B—C17B—H17B 119.00
H15B—C15A—H15C 109.00 C17B—C18B—H18B 120.00
C14A—C15A—H15B 109.00 C19B—C18B—H18B 120.00
C14A—C15A—H15C 110.00 C18B—C19B—H19B 121.00
C14A—C15A—H15A 109.00 C20B—C19B—H19B 121.00
H15A—C15A—H15B 109.00 C16B—C21B—H21 120.00
C18A—C17A—H17A 119.00 C20B—C21B—H21 120.00
C13A—N1A—N2A—C14A 172.6 (2) C21A—C16A—C17A—C18A 2.2 (4)
N2A—N1A—C13A—O1A 173.5 (2) C17A—C16A—C21A—C20A −1.2 (4)
N2A—N1A—C13A—C11A −8.1 (3) C14A—C16A—C21A—C20A 178.7 (2)
N1A—N2A—C14A—C15A −2.2 (4) C16A—C17A—C18A—C19A −1.6 (5)
N1A—N2A—C14A—C16A 178.7 (2) C17A—C18A—C19A—C20A 0.0 (5)
O2A—N3A—C20A—C19A 175.9 (3) C18A—C19A—C20A—N3A −179.8 (3)
O2A—N3A—C20A—C21A −4.8 (4) C18A—C19A—C20A—C21A 1.0 (5)
O3A—N3A—C20A—C19A −3.4 (4) C19A—C20A—C21A—C16A −0.4 (4)
O3A—N3A—C20A—C21A 175.9 (3) N3A—C20A—C21A—C16A −179.6 (2)
N2B—N1B—C13B—C11B 1.1 (4) C1B—C3B—C4B—C5B 178.4 (3)
C13B—N1B—N2B—C14B −178.8 (2) C2B—C3B—C4B—C5B −56.8 (4)
N2B—N1B—C13B—O1B −177.7 (2) C3B—C4B—C5B—C6B −59.8 (4)
N1B—N2B—C14B—C15B 1.9 (4) C3B—C4B—C5B—C10B 118.8 (3)
N1B—N2B—C14B—C16B −177.5 (2) C4B—C5B—C6B—C7B 177.5 (2)
O2B—N3B—C20B—C21B −2.0 (5) C10B—C5B—C6B—C7B −1.2 (4)
O2B—N3B—C20B—C19B 179.5 (4) C4B—C5B—C10B—C9B −178.4 (3)
O3B—N3B—C20B—C21B 179.1 (3) C6B—C5B—C10B—C9B 0.3 (4)
O3B—N3B—C20B—C19B 0.6 (5) C5B—C6B—C7B—C8B 1.1 (4)
C2A—C3A—C4A—C5A −170.2 (3) C6B—C7B—C8B—C9B 0.0 (3)
C1A—C3A—C4A—C5A 62.6 (4) C6B—C7B—C8B—C11B −176.5 (2)
C3A—C4A—C5A—C6A −92.9 (4) C7B—C8B—C9B—C10B −0.9 (4)
C3A—C4A—C5A—C10A 84.7 (4) C11B—C8B—C9B—C10B 175.6 (2)
C4A—C5A—C6A—C7A 177.8 (3) C7B—C8B—C11B—C12B 80.2 (3)
C10A—C5A—C6A—C7A 0.1 (5) C7B—C8B—C11B—C13B −41.9 (3)
C4A—C5A—C10A—C9A −178.6 (3) C9B—C8B—C11B—C12B −96.2 (3)
C6A—C5A—C10A—C9A −0.9 (5) C9B—C8B—C11B—C13B 141.7 (2)
C5A—C6A—C7A—C8A 0.3 (5) C8B—C9B—C10B—C5B 0.8 (4)
C6A—C7A—C8A—C9A 0.2 (4) C8B—C11B—C13B—O1B 105.5 (3)
C6A—C7A—C8A—C11A 179.4 (3) C8B—C11B—C13B—N1B −73.2 (3)
C7A—C8A—C9A—C10A −1.0 (4) C12B—C11B—C13B—O1B −16.4 (3)
C7A—C8A—C11A—C13A 64.8 (3) C12B—C11B—C13B—N1B 164.9 (2)
C9A—C8A—C11A—C12A 122.2 (3) N2B—C14B—C16B—C17B 178.0 (3)
C9A—C8A—C11A—C13A −115.9 (3) N2B—C14B—C16B—C21B −0.3 (4)
C11A—C8A—C9A—C10A 179.8 (2) C15B—C14B—C16B—C17B −1.3 (4)
C7A—C8A—C11A—C12A −57.0 (3) C15B—C14B—C16B—C21B −179.6 (3)
C8A—C9A—C10A—C5A 1.4 (4) C14B—C16B—C17B—C18B −178.1 (3)
C12A—C11A—C13A—O1A 37.8 (3) C21B—C16B—C17B—C18B 0.3 (5)
C8A—C11A—C13A—O1A −86.1 (3) C14B—C16B—C21B—C20B 178.7 (2)
C8A—C11A—C13A—N1A 95.5 (3) C17B—C16B—C21B—C20B 0.4 (4)
C12A—C11A—C13A—N1A −140.6 (2) C16B—C17B—C18B—C19B −0.4 (6)
N2A—C14A—C16A—C21A −4.6 (4) C17B—C18B—C19B—C20B −0.2 (6)
C15A—C14A—C16A—C17A −3.9 (4) C18B—C19B—C20B—N3B 179.3 (3)
N2A—C14A—C16A—C17A 175.3 (2) C18B—C19B—C20B—C21B 0.9 (5)
C15A—C14A—C16A—C21A 176.2 (3) N3B—C20B—C21B—C16B −179.4 (3)
C14A—C16A—C17A—C18A −177.7 (3) C19B—C20B—C21B—C16B −0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A 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
C11A—H11A···N2A 0.98 2.41 2.803 (4) 103
C15A—H15C···O1Bi 0.96 2.41 3.252 (4) 147
C15A—H15C···N1A 0.96 2.41 2.791 (4) 103

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2579).

References

  1. Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. [DOI] [PubMed]
  2. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  3. Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o445. [DOI] [PMC free article] [PubMed]
  4. 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.
  5. Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, Oxfordshire, England.
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  8. Terzioglu, N. & Gursoy, A. (2003). Eur. J. Med. Chem. 38, 781–786. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019892/gk2579sup1.cif

e-69-o1333-sup1.cif (45.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019892/gk2579Isup2.hkl

e-69-o1333-Isup2.hkl (432.5KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536813019892/gk2579Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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