(E)-N-(3,3-Di­phenyl­allyl­idene)naph­thal­en-1-amine

Lee, J.K.; Nam, K.D.; Cha, J.H.; Cho, Y.S.; Lee, J.K.

doi:10.1107/S1600536813014888

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1025

https://doi.org/10.1107/S1600536813014888

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(E)-N-(3,3-Diphenylallylidene)naphthalen-1-amine

Jae Kyun Lee,^a ^* Kee Dal Nam,^b Joo Hwan Cha,^c Yong Seo Cho ^a and Joon Kyun Lee ^d

^aCenter for Neuro-Medicine, Brain Science Institute, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, ^bChemical Kinomics Research Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, ^cAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and ^dKorea Institute of Industrial Technology, 143 Hanggaulro, Sangnok-gu, Ansan-si, Gyeonggi-do 426-910, Republic of Korea
^*Correspondence e-mail: j9601@kist.re.kr

(Received 9 May 2013; accepted 30 May 2013; online 8 June 2013)

The title compound, C₂₅H₁₉N, adopts an E conformation about the C=N bond. The naphthalene ring system and the phenyl rings form dihedral angles 38.1 (1), 46.9 (8) and 48.5 (1)°, respectively, with the mean plane of the central enimino fragment. The crystal packing exhibits no directional close contacts.

Related literature

For the crystal structures of related compounds studied recently by our group, see: Cha et al. (2012 ); Kang et al. (2012 ); Yu et al. (2013 ); Nam et al. (2013 ).

Experimental

Crystal data

C₂₅H₁₉N
M_r = 333.41
Orthorhombic, P b c a
a = 11.2203 (7) Å
b = 13.5658 (7) Å
c = 24.1946 (13) Å
V = 3682.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.986, T_max = 0.986
33578 measured reflections
4190 independent reflections
2080 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.197
S = 0.95
4190 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2006 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813014888/cv5411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014888/cv5411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813014888/cv5411Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2-phenylcinnamaldehyde derivatives contaning aniline (Cha et al., 2012; Kang et al., 2012; Yu et al., 2013) and naphthylamine (Nam et al., 2013), we present here the title compound.

The title compound (Fig. 1) adopts an (E) conformation about the C═N bond. The naphthalene bicycle C1–C10 and phenyl rings C14–C19 and C20–C25 form the dihedral angles 38.1 (1), 46.9 (8) and 48.5 (1)°, respectively, with the mean plane of the central N1–C11–C12 enimino fragment. The crystal packing exhibits no classical intermolecular contacts.

Related literature top

For the crystal structures of related compounds studied recently by our group, see: Cha et al. (2012); Kang et al. (2012); Yu et al. (2013); Nam et al. (2013).

Experimental top

In a solution of 1-naphthylamine (2.0 mmol) in anhydrous ethanol (50 mL) was treated with equimolar quantities of substituted 2-phenylcinnamaldehydes. The mixture was refluxed for 2 days, and the progress of reaction was monitored by TLC. After completion of reaction, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography to afford the title compound as a yellow solid in yield 92%. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.

Structure description top

For the crystal structures of related compounds studied recently by our group, see: Cha et al. (2012); Kang et al. (2012); Yu et al. (2013); Nam et al. (2013).

Computing details top

Data collection: RAPID–AUTO (Rigaku, 2006); cell refinement: RAPID–AUTO (Rigaku, 2006); data reduction: RAPID–AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoid.

(E)-N-(3,3-Diphenylallylidene)naphthalen-1-amine top

Crystal data top

C₂₅H₁₉N	Z = 8
M_r = 333.41	F(000) = 1408
Orthorhombic, Pbca	D_x = 1.203 Mg m⁻³
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71075 Å
a = 11.2203 (7) Å	µ = 0.07 mm⁻¹
b = 13.5658 (7) Å	T = 296 K
c = 24.1946 (13) Å	Block, yellow
V = 3682.7 (4) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4190 independent reflections
Radiation source: fine-focus sealed tube	2080 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −17→17
T_min = 0.986, T_max = 0.986	l = −31→30
33578 measured reflections

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.1186P)²] where P = (F_o² + 2F_c²)/3
4190 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₁₉N	V = 3682.7 (4) Å³
M_r = 333.41	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.2203 (7) Å	µ = 0.07 mm⁻¹
b = 13.5658 (7) Å	T = 296 K
c = 24.1946 (13) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4190 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2080 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.986	R_int = 0.070
33578 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 0.95	Δρ_max = 0.16 e Å⁻³
4190 reflections	Δρ_min = −0.25 e Å⁻³
235 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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.03605 (16)	0.37399 (12)	0.86987 (6)	0.0588 (5)
C1	−0.1297 (2)	0.27203 (18)	0.83686 (9)	0.0688 (6)
H1	−0.1143	0.2251	0.8640	0.083*
C2	−0.2224 (3)	0.2562 (2)	0.79886 (10)	0.0830 (8)
H2	−0.2682	0.1992	0.8013	0.100*
C3	−0.2458 (2)	0.3231 (2)	0.75873 (9)	0.0827 (8)
H3	−0.3079	0.3118	0.7341	0.099*
C4	−0.1772 (2)	0.4100 (2)	0.75384 (8)	0.0682 (7)
C5	−0.1976 (3)	0.4814 (3)	0.71211 (10)	0.0888 (9)
H5	−0.2569	0.4705	0.6860	0.107*
C6	−0.1321 (3)	0.5650 (3)	0.70969 (10)	0.0947 (10)
H6	−0.1471	0.6108	0.6819	0.114*
C7	−0.0421 (3)	0.5836 (2)	0.74842 (11)	0.0850 (8)
H7	0.0018	0.6416	0.7465	0.102*
C8	−0.0190 (2)	0.51646 (18)	0.78898 (9)	0.0690 (7)
H8	0.0406	0.5295	0.8147	0.083*
C9	−0.0839 (2)	0.42754 (17)	0.79262 (8)	0.0582 (6)
C10	−0.06209 (19)	0.35522 (16)	0.83444 (8)	0.0564 (5)
C11	0.0290 (2)	0.35090 (15)	0.92139 (8)	0.0558 (5)
H11	−0.0394	0.3213	0.9354	0.067*
C12	0.1286 (2)	0.37159 (14)	0.95689 (8)	0.0562 (5)
H12	0.1979	0.3923	0.9393	0.067*
C13	0.13445 (18)	0.36485 (14)	1.01268 (8)	0.0522 (5)
C14	0.03384 (19)	0.33393 (15)	1.04830 (8)	0.0534 (5)
C15	−0.0793 (2)	0.37540 (16)	1.04349 (9)	0.0630 (6)
H15	−0.0937	0.4227	1.0165	0.076*
C16	−0.1706 (2)	0.3467 (2)	1.07863 (10)	0.0761 (7)
H16	−0.2457	0.3750	1.0751	0.091*
C17	−0.1506 (3)	0.2765 (2)	1.11871 (10)	0.0793 (8)
H17	−0.2122	0.2571	1.1420	0.095*
C18	−0.0399 (3)	0.23538 (18)	1.12413 (9)	0.0747 (7)
H18	−0.0264	0.1881	1.1513	0.090*
C19	0.0517 (2)	0.26348 (16)	1.08965 (8)	0.0642 (6)
H19	0.1266	0.2351	1.0939	0.077*
C20	0.24624 (19)	0.39592 (14)	1.04092 (8)	0.0522 (5)
C21	0.2411 (2)	0.45116 (16)	1.08939 (8)	0.0655 (6)
H21	0.1676	0.4635	1.1058	0.079*
C22	0.3434 (3)	0.48772 (19)	1.11332 (10)	0.0760 (7)
H22	0.3385	0.5257	1.1452	0.091*
C23	0.4527 (3)	0.46821 (19)	1.09016 (10)	0.0781 (7)
H23	0.5216	0.4933	1.1062	0.094*
C24	0.4600 (2)	0.41132 (18)	1.04309 (10)	0.0702 (6)
H24	0.5340	0.3969	1.0279	0.084*
C25	0.3577 (2)	0.37575 (16)	1.01848 (8)	0.0604 (6)
H25	0.3634	0.3379	0.9865	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0562 (11)	0.0734 (12)	0.0467 (9)	0.0012 (9)	−0.0046 (8)	0.0029 (8)
C1	0.0738 (16)	0.0759 (15)	0.0568 (12)	−0.0053 (13)	−0.0020 (11)	−0.0047 (11)
C2	0.0819 (19)	0.0996 (19)	0.0675 (15)	−0.0148 (15)	−0.0064 (14)	−0.0201 (14)
C3	0.0614 (16)	0.127 (2)	0.0593 (13)	0.0046 (16)	−0.0104 (12)	−0.0266 (15)
C4	0.0574 (15)	0.1024 (18)	0.0447 (11)	0.0215 (13)	−0.0033 (10)	−0.0105 (12)
C5	0.080 (2)	0.133 (3)	0.0530 (13)	0.042 (2)	−0.0055 (13)	−0.0045 (15)
C6	0.108 (3)	0.119 (2)	0.0568 (15)	0.052 (2)	0.0038 (15)	0.0169 (16)
C7	0.087 (2)	0.0966 (18)	0.0716 (15)	0.0220 (15)	0.0105 (14)	0.0225 (14)
C8	0.0638 (15)	0.0851 (17)	0.0580 (13)	0.0107 (13)	0.0052 (11)	0.0094 (12)
C9	0.0501 (13)	0.0809 (15)	0.0436 (10)	0.0106 (11)	0.0032 (9)	−0.0022 (10)
C10	0.0531 (13)	0.0728 (14)	0.0432 (10)	0.0037 (11)	−0.0006 (9)	−0.0030 (9)
C11	0.0597 (13)	0.0604 (12)	0.0473 (10)	−0.0005 (10)	−0.0016 (9)	0.0012 (9)
C12	0.0552 (13)	0.0609 (13)	0.0524 (11)	−0.0005 (10)	−0.0043 (10)	0.0020 (9)
C13	0.0575 (13)	0.0496 (11)	0.0494 (10)	0.0035 (9)	−0.0017 (9)	−0.0002 (9)
C14	0.0587 (13)	0.0538 (11)	0.0477 (10)	0.0004 (10)	−0.0015 (9)	−0.0044 (9)
C15	0.0639 (15)	0.0627 (13)	0.0623 (12)	0.0056 (11)	0.0012 (11)	−0.0043 (10)
C16	0.0628 (16)	0.0831 (16)	0.0824 (16)	0.0050 (13)	0.0132 (13)	−0.0138 (14)
C17	0.083 (2)	0.0854 (18)	0.0691 (14)	−0.0109 (15)	0.0213 (14)	−0.0095 (13)
C18	0.0897 (19)	0.0763 (16)	0.0580 (13)	−0.0081 (14)	0.0090 (13)	0.0040 (11)
C19	0.0681 (15)	0.0682 (13)	0.0563 (12)	−0.0009 (11)	−0.0006 (11)	0.0054 (10)
C20	0.0568 (13)	0.0519 (11)	0.0480 (10)	−0.0005 (10)	−0.0030 (9)	0.0045 (8)
C21	0.0706 (15)	0.0692 (14)	0.0568 (12)	−0.0008 (12)	−0.0029 (11)	−0.0056 (10)
C22	0.089 (2)	0.0747 (16)	0.0643 (14)	−0.0092 (14)	−0.0104 (14)	−0.0122 (12)
C23	0.0777 (19)	0.0796 (16)	0.0770 (16)	−0.0184 (14)	−0.0201 (14)	0.0043 (13)
C24	0.0618 (15)	0.0793 (16)	0.0696 (14)	−0.0057 (12)	−0.0055 (12)	0.0098 (12)
C25	0.0607 (14)	0.0658 (13)	0.0547 (12)	0.0016 (11)	−0.0020 (10)	0.0003 (10)

Geometric parameters (Å, º) top

N1—C11	1.288 (2)	C13—C14	1.481 (3)
N1—C10	1.419 (3)	C13—C20	1.489 (3)
C1—C10	1.361 (3)	C14—C15	1.394 (3)
C1—C2	1.405 (3)	C14—C19	1.398 (3)
C1—H1	0.9300	C15—C16	1.387 (3)
C2—C3	1.355 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.377 (4)
C3—C4	1.412 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.368 (4)
C4—C5	1.417 (4)	C17—H17	0.9300
C4—C9	1.425 (3)	C18—C19	1.378 (3)
C5—C6	1.353 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.400 (4)	C20—C25	1.391 (3)
C6—H6	0.9300	C20—C21	1.393 (3)
C7—C8	1.364 (3)	C21—C22	1.379 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.412 (3)	C22—C23	1.373 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.430 (3)	C23—C24	1.378 (3)
C11—C12	1.437 (3)	C23—H23	0.9300
C11—H11	0.9300	C24—C25	1.380 (3)
C12—C13	1.355 (3)	C24—H24	0.9300
C12—H12	0.9300	C25—H25	0.9300

C11—N1—C10	119.57 (18)	C12—C13—C20	118.61 (19)
C10—C1—C2	120.7 (2)	C14—C13—C20	117.07 (16)
C10—C1—H1	119.6	C15—C14—C19	117.8 (2)
C2—C1—H1	119.6	C15—C14—C13	122.11 (19)
C3—C2—C1	120.7 (3)	C19—C14—C13	120.05 (19)
C3—C2—H2	119.7	C16—C15—C14	120.5 (2)
C1—C2—H2	119.7	C16—C15—H15	119.7
C2—C3—C4	120.9 (2)	C14—C15—H15	119.7
C2—C3—H3	119.6	C17—C16—C15	120.4 (2)
C4—C3—H3	119.6	C17—C16—H16	119.8
C3—C4—C5	122.8 (2)	C15—C16—H16	119.8
C3—C4—C9	119.0 (2)	C18—C17—C16	119.8 (2)
C5—C4—C9	118.2 (3)	C18—C17—H17	120.1
C6—C5—C4	121.1 (3)	C16—C17—H17	120.1
C6—C5—H5	119.5	C17—C18—C19	120.4 (2)
C4—C5—H5	119.5	C17—C18—H18	119.8
C5—C6—C7	120.9 (3)	C19—C18—H18	119.8
C5—C6—H6	119.6	C18—C19—C14	121.0 (2)
C7—C6—H6	119.6	C18—C19—H19	119.5
C8—C7—C6	119.9 (3)	C14—C19—H19	119.5
C8—C7—H7	120.0	C25—C20—C21	118.2 (2)
C6—C7—H7	120.0	C25—C20—C13	121.51 (17)
C7—C8—C9	121.1 (2)	C21—C20—C13	120.2 (2)
C7—C8—H8	119.4	C22—C21—C20	120.8 (2)
C9—C8—H8	119.4	C22—C21—H21	119.6
C8—C9—C4	118.7 (2)	C20—C21—H21	119.6
C8—C9—C10	122.8 (2)	C23—C22—C21	120.2 (2)
C4—C9—C10	118.5 (2)	C23—C22—H22	119.9
C1—C10—N1	123.73 (19)	C21—C22—H22	119.9
C1—C10—C9	120.2 (2)	C22—C23—C24	119.9 (2)
N1—C10—C9	115.94 (19)	C22—C23—H23	120.1
N1—C11—C12	118.9 (2)	C24—C23—H23	120.1
N1—C11—H11	120.6	C23—C24—C25	120.2 (2)
C12—C11—H11	120.6	C23—C24—H24	119.9
C13—C12—C11	128.3 (2)	C25—C24—H24	119.9
C13—C12—H12	115.8	C24—C25—C20	120.7 (2)
C11—C12—H12	115.8	C24—C25—H25	119.7
C12—C13—C14	124.21 (19)	C20—C25—H25	119.7

C10—C1—C2—C3	0.5 (4)	C11—C12—C13—C20	−176.53 (18)
C1—C2—C3—C4	0.5 (4)	C12—C13—C14—C15	−49.7 (3)
C2—C3—C4—C5	179.2 (2)	C20—C13—C14—C15	126.6 (2)
C2—C3—C4—C9	−1.3 (3)	C12—C13—C14—C19	132.6 (2)
C3—C4—C5—C6	178.1 (2)	C20—C13—C14—C19	−51.1 (3)
C9—C4—C5—C6	−1.4 (4)	C19—C14—C15—C16	−0.4 (3)
C4—C5—C6—C7	0.0 (4)	C13—C14—C15—C16	−178.12 (19)
C5—C6—C7—C8	0.5 (4)	C14—C15—C16—C17	−0.2 (3)
C6—C7—C8—C9	0.4 (4)	C15—C16—C17—C18	0.4 (4)
C7—C8—C9—C4	−1.7 (3)	C16—C17—C18—C19	−0.2 (4)
C7—C8—C9—C10	179.8 (2)	C17—C18—C19—C14	−0.3 (4)
C3—C4—C9—C8	−177.3 (2)	C15—C14—C19—C18	0.6 (3)
C5—C4—C9—C8	2.2 (3)	C13—C14—C19—C18	178.42 (19)
C3—C4—C9—C10	1.2 (3)	C12—C13—C20—C25	−38.9 (3)
C5—C4—C9—C10	−179.31 (19)	C14—C13—C20—C25	144.7 (2)
C2—C1—C10—N1	−177.1 (2)	C12—C13—C20—C21	137.5 (2)
C2—C1—C10—C9	−0.6 (3)	C14—C13—C20—C21	−38.9 (3)
C11—N1—C10—C1	−40.3 (3)	C25—C20—C21—C22	2.3 (3)
C11—N1—C10—C9	143.1 (2)	C13—C20—C21—C22	−174.3 (2)
C8—C9—C10—C1	178.2 (2)	C20—C21—C22—C23	−1.4 (4)
C4—C9—C10—C1	−0.2 (3)	C21—C22—C23—C24	−0.5 (4)
C8—C9—C10—N1	−5.0 (3)	C22—C23—C24—C25	1.4 (4)
C4—C9—C10—N1	176.55 (18)	C23—C24—C25—C20	−0.5 (3)
C10—N1—C11—C12	−179.19 (18)	C21—C20—C25—C24	−1.3 (3)
N1—C11—C12—C13	171.0 (2)	C13—C20—C25—C24	175.22 (19)
C11—C12—C13—C14	−0.3 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉N
M_r	333.41
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.2203 (7), 13.5658 (7), 24.1946 (13)
V (Å³)	3682.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.986, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	33578, 4190, 2080
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.197, 0.95
No. of reflections	4190
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: RAPID–AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Acknowledgements

Financial support from the Korean Institute of Science and Technology (KIST) is gratefully acknowledged.

References

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