1-(2,6-Diisopropyl­phen­oxy)-4-phenyl­phthalazine

Tong, B.; Mei, Q.

doi:10.1107/S1600536812033296

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2578

https://doi.org/10.1107/S1600536812033296

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1-(2,6-Diisopropylphenoxy)-4-phenylphthalazine

Bihai Tong ^a ^* and Qunying Mei ^b

^aCollege of Metallurgy and Resources, Anhui University of Technology, Maanshan 243002, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, School Library, Anhui University of Technology, Maanshan 243002, People's Republic of China
^*Correspondence e-mail: tongbihai@163.com

(Received 12 July 2012; accepted 23 July 2012; online 28 July 2012)

In the title molecule, C₂₆H₂₆N₂O, the phenyl and phenoxy rings form dihedral angles of 54.66 (7) and 84.83 (6)°, respectively, with the phthalazine mean plane. The crystal packing exhibits weak C—H⋯π interactions.

Related literature

For details of the synthesis, see: Tong et al. (2008 , 2012 ). For related structures, see: Dilek et al. (2004 ); Rajnikant et al. (2006 ); Sakthivel et al. (2011 ).

Experimental

Crystal data

C₂₆H₂₆N₂O
M_r = 382.49
Monoclinic, P 2₁ /c
a = 14.079 (10) Å
b = 8.369 (6) Å
c = 19.244 (13) Å
β = 109.104 (9)°
V = 2143 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 273 K
0.31 × 0.29 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.978, T_max = 0.990
9404 measured reflections
3596 independent reflections
2028 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.165
S = 0.90
3596 reflections
267 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg	0.93	2.77	3.624 (2)	154

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812033296/cv5322sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033296/cv5322Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812033296/cv5322Isup3.cml

checkCIF report

Comment top

Phthalazine is a well known heterocyclic system which is widely used in coordination chemistry and pharmaceutical chemistry. Recently, we have reported the direct synthesis of a series of highly efficient tris-cyclometalated iridium(III) complexes using phenylphthalazine derivatives as ligands (Tong et al., 2008). However, the 2, 6-dimethylphenoxyl groups of phenylphthalazine derivatives hydrolyzate easily in the coordination procedure (Tong et al., 2012). In order to suppress the hydrolyzation process, the title molecule was synthesized as the ligand of cyclometalated iridium(III) complexes.

In the title molecule (Fig. 1), the phthalazine moiety consists of a benzene and a pyridazine rings fused together and shows a planar conformation; the dihedral angle between these rings is 2.00 (6)°. A phenyl and a phenoxyl rings are substituted on the pyridazine ring and dihedral angle of these rings with the pyridazine ring are 54.66 (7) and 84.83 (6)°, respectively. The molecular dimensions in the title compound are in agreement with the corresponding molecular dimensions reported for closely related compounds (Dilek et al., 2004; Rajnikant et al., 2006; Sakthivel et al., 2011). In the crystal, the molecules are held together via the weak C—H···π interactions (Table 1).

Related literature top

For details of the synthesis, see: Tong et al. (2008, 2012). For related structures, see: Dilek et al. (2004); Rajnikant et al. (2006); Sakthivel et al. (2011).

Experimental top

The title compound was obtained in 89% yield by refluxing 1-chloro-4- phenylphthalazine (4.8 g, 20 mmol), 2,6-diisopropylphenol (2.5 g, 20 mmol) and potassium carbonate (2.8 g, 20 mmol) in N,N-dimethylformamide (50 ml) at 383 K for 5 h under nitrogen atmosphere. The crystals suitable for crystallographic study were grow from ethanol by slow evaporation at room temperature.

Structure description top

For details of the synthesis, see: Tong et al. (2008, 2012). For related structures, see: Dilek et al. (2004); Rajnikant et al. (2006); Sakthivel et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the atomic labeling and 30% probability displacement ellipsoids. H atoms omitted for clarity.

1-(2,6-Diisopropylphenoxy)-4-phenylphthalazine top

Crystal data top

C₂₆H₂₆N₂O	F(000) = 816
M_r = 382.49	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1750 reflections
a = 14.079 (10) Å	θ = 2.7–22.8°
b = 8.369 (6) Å	µ = 0.07 mm⁻¹
c = 19.244 (13) Å	T = 273 K
β = 109.104 (9)°	Block, colourless
V = 2143 (3) Å³	0.31 × 0.29 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3596 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→12
T_min = 0.978, T_max = 0.990	k = −9→9
9404 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.90	(Δ/σ)_max < 0.001
3596 reflections	Δρ_max = 0.16 e Å⁻³
267 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (16)

Crystal data top

C₂₆H₂₆N₂O	V = 2143 (3) Å³
M_r = 382.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.079 (10) Å	µ = 0.07 mm⁻¹
b = 8.369 (6) Å	T = 273 K
c = 19.244 (13) Å	0.31 × 0.29 × 0.14 mm
β = 109.104 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3596 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2028 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.990	R_int = 0.036
9404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 0.90	Δρ_max = 0.16 e Å⁻³
3596 reflections	Δρ_min = −0.15 e Å⁻³
267 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.34098 (10)	0.39831 (14)	0.11904 (7)	0.0538 (4)
N1	0.21896 (13)	0.28031 (18)	0.02336 (10)	0.0589 (5)
N2	0.13859 (13)	0.29298 (18)	−0.04103 (10)	0.0586 (5)
C1	−0.05395 (18)	0.5056 (3)	−0.26486 (13)	0.0669 (7)
H1	−0.0493	0.5583	−0.3061	0.080*
C2	0.02474 (16)	0.5119 (2)	−0.19941 (12)	0.0585 (6)
H2	0.0821	0.5702	−0.1967	0.070*
C3	0.01925 (14)	0.4318 (2)	−0.13752 (12)	0.0476 (5)
C4	−0.06648 (16)	0.3467 (3)	−0.14229 (13)	0.0598 (6)
H4	−0.0711	0.2920	−0.1015	0.072*
C5	−0.14592 (17)	0.3428 (3)	−0.20810 (15)	0.0703 (7)
H5	−0.2041	0.2866	−0.2110	0.084*
C6	−0.13891 (19)	0.4214 (3)	−0.26883 (15)	0.0707 (8)
H6	−0.1921	0.4175	−0.3129	0.085*
C7	0.11235 (17)	0.7351 (2)	−0.05706 (12)	0.0573 (6)
H7	0.0554	0.7465	−0.0982	0.069*
C8	0.16031 (18)	0.8674 (2)	−0.02080 (13)	0.0628 (7)
H8	0.1361	0.9684	−0.0379	0.075*
C9	0.24466 (17)	0.8534 (2)	0.04120 (12)	0.0605 (6)
H9	0.2776	0.9448	0.0645	0.073*
C10	0.27973 (15)	0.7063 (2)	0.06820 (12)	0.0519 (6)
H10	0.3353	0.6973	0.1106	0.062*
C11	0.23150 (14)	0.5686 (2)	0.03174 (11)	0.0443 (5)
C12	0.14875 (14)	0.5808 (2)	−0.03242 (11)	0.0452 (5)
C13	0.10543 (15)	0.4343 (2)	−0.06729 (11)	0.0480 (5)
C14	0.26126 (14)	0.4091 (2)	0.05578 (11)	0.0471 (5)
C15	0.38186 (15)	0.2456 (2)	0.14320 (11)	0.0474 (5)
C16	0.46379 (16)	0.1981 (2)	0.12297 (12)	0.0560 (6)
C17	0.50782 (17)	0.0537 (3)	0.15145 (14)	0.0668 (7)
H17	0.5622	0.0166	0.1387	0.080*
C18	0.47331 (18)	−0.0360 (3)	0.19788 (13)	0.0666 (7)
H18	0.5039	−0.1328	0.2160	0.080*
C19	0.39335 (17)	0.0175 (2)	0.21759 (12)	0.0612 (6)
H19	0.3707	−0.0437	0.2494	0.073*
C20	0.34555 (15)	0.1613 (2)	0.19098 (11)	0.0517 (6)
C21	0.5026 (2)	0.2971 (3)	0.07181 (16)	0.0760 (8)
H21	0.4835	0.4084	0.0759	0.091*
C22	0.4544 (2)	0.2473 (4)	−0.00709 (16)	0.1097 (11)
H22A	0.4731	0.1392	−0.0132	0.165*
H22B	0.4767	0.3166	−0.0384	0.165*
H22C	0.3826	0.2543	−0.0200	0.165*
C23	0.6165 (2)	0.2921 (4)	0.09240 (17)	0.1019 (10)
H23A	0.6368	0.1891	0.0804	0.153*
H23B	0.6465	0.3109	0.1442	0.153*
H23C	0.6382	0.3731	0.0656	0.153*
C24	0.25826 (17)	0.2197 (3)	0.21399 (14)	0.0654 (7)
H24	0.2486	0.3334	0.2016	0.079*
C25	0.16130 (18)	0.1335 (4)	0.17186 (16)	0.0937 (9)
H25A	0.1694	0.0209	0.1815	0.141*
H25B	0.1459	0.1524	0.1201	0.141*
H25C	0.1075	0.1729	0.1874	0.141*
C26	0.2778 (2)	0.2039 (3)	0.29605 (15)	0.0852 (8)
H26A	0.2816	0.0929	0.3092	0.128*
H26B	0.2240	0.2535	0.3085	0.128*
H26C	0.3401	0.2555	0.3224	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0598 (9)	0.0348 (7)	0.0532 (9)	0.0037 (6)	0.0002 (7)	0.0011 (6)
N1	0.0646 (11)	0.0363 (9)	0.0595 (12)	−0.0007 (8)	−0.0018 (9)	0.0003 (8)
N2	0.0653 (11)	0.0372 (9)	0.0587 (12)	−0.0017 (8)	0.0003 (9)	0.0007 (8)
C1	0.0774 (16)	0.0641 (14)	0.0521 (15)	0.0064 (13)	0.0114 (12)	−0.0010 (11)
C2	0.0643 (13)	0.0506 (12)	0.0563 (15)	−0.0018 (10)	0.0138 (11)	−0.0013 (11)
C3	0.0519 (12)	0.0370 (10)	0.0505 (14)	0.0041 (9)	0.0121 (10)	−0.0036 (9)
C4	0.0614 (14)	0.0543 (13)	0.0605 (15)	−0.0038 (11)	0.0155 (12)	−0.0015 (11)
C5	0.0563 (14)	0.0654 (15)	0.0784 (19)	−0.0089 (12)	0.0072 (13)	−0.0137 (13)
C6	0.0710 (16)	0.0656 (15)	0.0588 (17)	0.0075 (13)	−0.0016 (13)	−0.0094 (12)
C7	0.0664 (13)	0.0404 (11)	0.0563 (14)	0.0078 (10)	0.0081 (11)	0.0039 (10)
C8	0.0878 (16)	0.0348 (10)	0.0587 (15)	0.0072 (11)	0.0145 (13)	0.0019 (10)
C9	0.0790 (16)	0.0352 (11)	0.0620 (15)	−0.0052 (10)	0.0157 (13)	−0.0046 (10)
C10	0.0599 (13)	0.0419 (11)	0.0499 (13)	−0.0044 (9)	0.0127 (10)	−0.0039 (9)
C11	0.0489 (11)	0.0346 (10)	0.0489 (13)	−0.0002 (8)	0.0150 (10)	0.0007 (8)
C12	0.0499 (11)	0.0380 (10)	0.0471 (13)	0.0017 (9)	0.0151 (10)	0.0000 (8)
C13	0.0511 (11)	0.0382 (10)	0.0516 (14)	0.0016 (9)	0.0124 (10)	0.0012 (9)
C14	0.0503 (12)	0.0363 (10)	0.0499 (13)	0.0009 (9)	0.0100 (10)	0.0011 (9)
C15	0.0531 (12)	0.0356 (10)	0.0431 (12)	0.0004 (9)	0.0015 (10)	−0.0001 (8)
C16	0.0579 (13)	0.0504 (12)	0.0547 (14)	0.0041 (11)	0.0115 (11)	−0.0023 (10)
C17	0.0661 (14)	0.0667 (14)	0.0645 (16)	0.0174 (12)	0.0169 (12)	0.0064 (12)
C18	0.0709 (15)	0.0567 (13)	0.0616 (16)	0.0210 (12)	0.0072 (13)	0.0125 (11)
C19	0.0735 (15)	0.0501 (12)	0.0541 (15)	0.0063 (11)	0.0128 (12)	0.0103 (10)
C20	0.0558 (12)	0.0428 (11)	0.0486 (13)	0.0022 (9)	0.0062 (10)	−0.0012 (9)
C21	0.0927 (19)	0.0602 (14)	0.086 (2)	0.0058 (13)	0.0440 (16)	0.0081 (13)
C22	0.117 (2)	0.139 (3)	0.069 (2)	0.004 (2)	0.0252 (18)	0.0288 (19)
C23	0.095 (2)	0.127 (3)	0.095 (2)	−0.0228 (19)	0.0463 (18)	−0.0186 (19)
C24	0.0721 (15)	0.0506 (12)	0.0747 (18)	0.0056 (11)	0.0255 (13)	0.0055 (11)
C25	0.0593 (16)	0.127 (2)	0.092 (2)	0.0058 (16)	0.0200 (15)	0.0062 (18)
C26	0.0941 (19)	0.0898 (19)	0.074 (2)	−0.0024 (15)	0.0309 (16)	−0.0057 (15)

Geometric parameters (Å, º) top

O1—C14	1.362 (2)	C15—C20	1.383 (3)
O1—C15	1.416 (2)	C15—C16	1.391 (3)
N1—C14	1.289 (2)	C16—C17	1.386 (3)
N1—N2	1.382 (2)	C16—C21	1.519 (3)
N2—C13	1.311 (2)	C17—C18	1.372 (3)
C1—C6	1.369 (3)	C17—H17	0.9300
C1—C2	1.380 (3)	C18—C19	1.375 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.390 (3)	C19—C20	1.392 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.379 (3)	C20—C24	1.517 (3)
C3—C13	1.492 (3)	C21—C22	1.505 (4)
C4—C5	1.389 (3)	C21—C23	1.522 (4)
C4—H4	0.9300	C21—H21	0.9800
C5—C6	1.373 (4)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C8	1.364 (3)	C23—H23A	0.9600
C7—C12	1.412 (3)	C23—H23B	0.9600
C7—H7	0.9300	C23—H23C	0.9600
C8—C9	1.386 (3)	C24—C26	1.518 (4)
C8—H8	0.9300	C24—C25	1.522 (3)
C9—C10	1.364 (3)	C24—H24	0.9800
C9—H9	0.9300	C25—H25A	0.9600
C10—C11	1.403 (3)	C25—H25B	0.9600
C10—H10	0.9300	C25—H25C	0.9600
C11—C12	1.397 (3)	C26—H26A	0.9600
C11—C14	1.430 (3)	C26—H26B	0.9600
C12—C13	1.435 (3)	C26—H26C	0.9600

C14—O1—C15	118.74 (13)	C15—C16—C21	122.17 (19)
C14—N1—N2	118.87 (15)	C18—C17—C16	121.8 (2)
C13—N2—N1	119.92 (15)	C18—C17—H17	119.1
C6—C1—C2	119.8 (2)	C16—C17—H17	119.1
C6—C1—H1	120.1	C17—C18—C19	119.9 (2)
C2—C1—H1	120.1	C17—C18—H18	120.1
C1—C2—C3	120.7 (2)	C19—C18—H18	120.1
C1—C2—H2	119.6	C18—C19—C20	121.4 (2)
C3—C2—H2	119.6	C18—C19—H19	119.3
C4—C3—C2	119.00 (19)	C20—C19—H19	119.3
C4—C3—C13	120.14 (19)	C15—C20—C19	116.5 (2)
C2—C3—C13	120.84 (19)	C15—C20—C24	122.73 (18)
C3—C4—C5	119.9 (2)	C19—C20—C24	120.8 (2)
C3—C4—H4	120.0	C22—C21—C16	111.3 (2)
C5—C4—H4	120.0	C22—C21—C23	110.1 (2)
C6—C5—C4	120.3 (2)	C16—C21—C23	112.9 (2)
C6—C5—H5	119.9	C22—C21—H21	107.4
C4—C5—H5	119.9	C16—C21—H21	107.4
C1—C6—C5	120.3 (2)	C23—C21—H21	107.4
C1—C6—H6	119.9	C21—C22—H22A	109.5
C5—C6—H6	119.9	C21—C22—H22B	109.5
C8—C7—C12	120.4 (2)	H22A—C22—H22B	109.5
C8—C7—H7	119.8	C21—C22—H22C	109.5
C12—C7—H7	119.8	H22A—C22—H22C	109.5
C7—C8—C9	120.84 (19)	H22B—C22—H22C	109.5
C7—C8—H8	119.6	C21—C23—H23A	109.5
C9—C8—H8	119.6	C21—C23—H23B	109.5
C10—C9—C8	120.39 (18)	H23A—C23—H23B	109.5
C10—C9—H9	119.8	C21—C23—H23C	109.5
C8—C9—H9	119.8	H23A—C23—H23C	109.5
C9—C10—C11	119.66 (19)	H23B—C23—H23C	109.5
C9—C10—H10	120.2	C20—C24—C26	112.8 (2)
C11—C10—H10	120.2	C20—C24—C25	111.3 (2)
C12—C11—C10	120.60 (16)	C26—C24—C25	109.8 (2)
C12—C11—C14	115.19 (16)	C20—C24—H24	107.6
C10—C11—C14	124.21 (18)	C26—C24—H24	107.6
C11—C12—C7	118.01 (16)	C25—C24—H24	107.6
C11—C12—C13	117.06 (16)	C24—C25—H25A	109.5
C7—C12—C13	124.90 (18)	C24—C25—H25B	109.5
N2—C13—C12	123.21 (18)	H25A—C25—H25B	109.5
N2—C13—C3	114.73 (16)	C24—C25—H25C	109.5
C12—C13—C3	122.06 (16)	H25A—C25—H25C	109.5
N1—C14—O1	119.47 (16)	H25B—C25—H25C	109.5
N1—C14—C11	125.72 (18)	C24—C26—H26A	109.5
O1—C14—C11	114.81 (16)	C24—C26—H26B	109.5
C20—C15—C16	124.11 (18)	H26A—C26—H26B	109.5
C20—C15—O1	118.68 (18)	C24—C26—H26C	109.5
C16—C15—O1	116.85 (18)	H26A—C26—H26C	109.5
C17—C16—C15	116.3 (2)	H26B—C26—H26C	109.5
C17—C16—C21	121.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg	0.93	2.77	3.624 (2)	154

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₂O
M_r	382.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.079 (10), 8.369 (6), 19.244 (13)
β (°)	109.104 (9)
V (Å³)	2143 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.31 × 0.29 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.978, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9404, 3596, 2028
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.165, 0.90
No. of reflections	3596
No. of parameters	267
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg	0.93	2.77	3.624 (2)	154

Acknowledgements

The authors thank the National Natural Science Foundation of China for financial support (grant No. 50903001).

References

Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dilek, N., Gunes, B., Ide, S., Ozcan, Y. & Tezcan, H. (2004). Anal. Sci. 20, x157–x158. CAS Google Scholar
Rajnikant, Dinesh, Kamni & Deshmukh, M. B. (2006). Crystallogr. Rep. 51, 615–618. Google Scholar
Sakthivel, K., Srinivasan, K. & Natarajan, S. (2011). Acta Cryst. E67, o3497. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tong, B. H., Mei, Q. B., Wang, S. J., Meng, Y. Z. & Wang, B. (2008). J. Mater. Chem. 18, 1636–1639. Web of Science CSD CrossRef CAS Google Scholar
Tong, B. H., Qiang, J. Y., Mei, Q. B., Wang, H. S. & Zhang, Q. F. (2012). Inorg. Chem. Commun. 17, 113–115. Web of Science CSD CrossRef CAS Google Scholar

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