4-Eth­oxy-N-(4-eth­oxy­phen­yl)-N-(4-nitro­phen­yl)aniline

Kong, M.; Hao, F.-Y.; Li, D.-D.; Wu, J.-Y.

doi:10.1107/S1600536813023386

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1470

doi:10.1107/S1600536813023386

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4-Ethoxy-N-(4-ethoxyphenyl)-N-(4-nitrophenyl)aniline

Ming Kong,^a Fu-Ying Hao,^a Dan-Dan Li ^a and Jie-Ying Wu ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: jywu1957@163.com

(Received 18 August 2013; accepted 20 August 2013; online 23 August 2013)

In the title molecule, C₂₂H₂₂N₂O₄, the ethoxyphenyl rings are oriented at dihedral angles of 69.31 (13) and 75.90 (13)° to the nitrophenyl ring and are twisted to each other, making a dihedral angle of 78.55 (13)°. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π interaction link the molecules into a three-dimensional supramolecular architecture.

Related literature

For applications of triphenylamine derivatives, see: Liu et al. (2012 ). For related compounds, see: Wang et al. (2011 ); Gudeika et al. (2012 ).

Experimental

Crystal data

C₂₂H₂₂N₂O₄
M_r = 378.42
Monoclinic, P 2₁ /c
a = 10.926 (5) Å
b = 18.380 (5) Å
c = 10.345 (5) Å
β = 107.998 (5)°
V = 1975.8 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
13718 measured reflections
3456 independent reflections
1884 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.178
S = 0.98
3456 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3ⁱ	0.93	2.56	3.371 (5)	146
C14—H14B⋯O4ⁱⁱ	0.96	2.55	3.458 (4)	158
C17—H17⋯Cg2ⁱⁱⁱ	0.93	2.78	3.700 (4)	173
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536813023386/xu5734sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023386/xu5734Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023386/xu5734Isup3.cml

checkCIF report

Comment top

As optical functional materials, triphenylamine derivative have attracted considerable attention, for their fluorescent characters, photostabilities and easy modification (Liu et al., 2012). Besides, the strong ability of electron delocalization in the title compound forms conjugated system which is one of the most excellent properties in two photon absorption materials field. Recent years many research groups choose triphenylamine as molecule core to synthesize a series of compounds (Wang et al., 2011; Gudeika et al., 2012). The length of the two nitrogen oxygen bonds in the crystal structure is nearly identical comparing their bond length data of 1.232 (3) and 1.229 (3) Å. This shows that the two bonds are intervenient between nitrogen oxygen single bond and nitrogen oxygen double bond. Also, the introduction of nitro group transforms the benzene ring plane generatting a dihedral angle of 2.8 (7)° being defined by the two planes of plane1 (C1, C2, C3) and plane2 (C4, C5, C6).

Related literature top

For applications of triphenylamine derivatives, see: Liu et al. (2012). For related compounds, see: Wang et al. (2011); Gudeika et al. (2012).

Experimental top

The intermediate 1-ethoxy-4-iodobenzene was synthesized by mixing 4-iodophenol (110 g, 0.5 mol) with bromoethane (218 g, 2 mol) in methanol (250 ml) in the presence of NaOH (40 g, 1 mol). The mixture was heated to reflux for 12 h. The solution was cooled to room temperature. White solid appeared when poured into a large amount of ice water. The solid was purified by 20% NaOH solution. The target product was obtained by the mixture of 4-nitroaniline (1.97 g, 15 mmol), 1-ethoxy-4-iodobenzene (10 g, 40 mmol), K₂CO₃ (13.8 g, 100 mmol), a few of L-proline and CuI in DMSO at 100 degrees celsius for 24 h. The mixture was washed with plenty of water and extracted by dichloromethane. The combined organic layer was dried over anhydrous MgSO₄ and concentrated using a rotary evaporator. The residue was purified by column chromatography. 1H NMR: (400 Hz, DMSO-d₆), d(p.p.m.):8.10 (d, 2H), 7.32 (d, 2H), 7.02 (d, 4H), 6.71 (d, 4H), 4.03 (q, 4H), 1.35 (t, 6H)

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound (I) showing 30% probability displacement ellipsoids.

4-Ethoxy-N-(4-ethoxyphenyl)-N-(4-nitrophenyl)aniline top

Crystal data top

C₂₂H₂₂N₂O₄	F(000) = 800
M_r = 378.42	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 1657 reflections
a = 10.926 (5) Å	θ = 2.3–19.5°
b = 18.380 (5) Å	µ = 0.09 mm⁻¹
c = 10.345 (5) Å	T = 298 K
β = 107.998 (5)°	Block, red
V = 1975.8 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1884 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
phi and ω scans	h = −12→12
13718 measured reflections	k = −20→21
3456 independent reflections	l = −12→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3456 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₂₂N₂O₄	V = 1975.8 (14) Å³
M_r = 378.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.926 (5) Å	µ = 0.09 mm⁻¹
b = 18.380 (5) Å	T = 298 K
c = 10.345 (5) Å	0.30 × 0.20 × 0.20 mm
β = 107.998 (5)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1884 reflections with I > 2σ(I)
13718 measured reflections	R_int = 0.050
3456 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 0.98	Δρ_max = 0.18 e Å⁻³
3456 reflections	Δρ_min = −0.17 e Å⁻³
255 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
N2	0.91897 (19)	0.16945 (11)	0.28936 (19)	0.0673 (6)
O1	0.56239 (17)	0.18864 (10)	−0.23010 (17)	0.0785 (6)
C9	0.8292 (2)	0.17241 (14)	0.1544 (2)	0.0607 (7)
C8	0.7178 (3)	0.11519 (15)	−0.0584 (3)	0.0708 (8)
H8	0.7016	0.0741	−0.1136	0.085*
C1	0.8614 (3)	0.04099 (13)	0.5958 (2)	0.0635 (7)
C15	1.0222 (2)	0.22159 (14)	0.3220 (2)	0.0609 (7)
C7	0.8063 (3)	0.11222 (15)	0.0714 (3)	0.0704 (7)
H7	0.8504	0.0692	0.1022	0.084*
C12	0.6541 (2)	0.17944 (15)	−0.1048 (2)	0.0633 (7)
C6	0.9971 (3)	0.11691 (14)	0.5137 (2)	0.0661 (7)
H6	1.0756	0.1404	0.5282	0.079*
N1	0.8397 (3)	−0.00099 (13)	0.7052 (3)	0.0829 (7)
C5	0.9009 (2)	0.12531 (13)	0.3896 (2)	0.0585 (6)
C17	1.0181 (3)	0.28165 (15)	0.4004 (2)	0.0708 (8)
H17	0.9496	0.2878	0.4349	0.085*
C10	0.7672 (2)	0.23642 (15)	0.1048 (3)	0.0674 (7)
H10	0.7842	0.2779	0.1590	0.081*
C3	0.7654 (3)	0.04742 (14)	0.4739 (3)	0.0697 (7)
H3	0.6872	0.0239	0.4612	0.084*
C4	0.7844 (3)	0.08837 (14)	0.3707 (2)	0.0687 (7)
H4	0.7196	0.0916	0.2878	0.082*
C19	1.1156 (3)	0.33271 (15)	0.4278 (3)	0.0744 (8)
H19	1.1132	0.3731	0.4810	0.089*
C20	1.2164 (3)	0.32350 (16)	0.3758 (3)	0.0708 (8)
O4	0.7323 (3)	−0.02692 (13)	0.6884 (2)	0.1098 (8)
C2	0.9775 (3)	0.07440 (14)	0.6150 (2)	0.0709 (8)
H2	1.0433	0.0684	0.6965	0.085*
O2	1.3142 (2)	0.37328 (13)	0.3914 (2)	0.1142 (8)
C11	0.6805 (2)	0.23998 (15)	−0.0236 (3)	0.0689 (7)
H11	0.6395	0.2837	−0.0555	0.083*
O3	0.9283 (3)	−0.00806 (12)	0.8122 (2)	0.1142 (8)
C18	1.2193 (3)	0.26372 (16)	0.2976 (3)	0.0738 (8)
H18	1.2874	0.2575	0.2625	0.089*
C16	1.1235 (3)	0.21351 (15)	0.2711 (2)	0.0675 (7)
H16	1.1265	0.1732	0.2179	0.081*
C13	0.5245 (3)	0.12818 (17)	−0.3152 (3)	0.0908 (9)
H13A	0.4952	0.0896	−0.2679	0.109*
H13B	0.5966	0.1101	−0.3418	0.109*
C14	0.4178 (3)	0.15093 (18)	−0.4383 (3)	0.1043 (11)
H14A	0.3416	0.1603	−0.4134	0.157*
H14B	0.4009	0.1128	−0.5049	0.157*
H14C	0.4424	0.1943	−0.4757	0.157*
C21	1.3504 (4)	0.4187 (2)	0.5060 (5)	0.1273 (14)
H21A	1.2735	0.4357	0.5246	0.153*
H21B	1.3948	0.4609	0.4861	0.153*
C22	1.4317 (4)	0.3834 (3)	0.6241 (4)	0.1555 (19)
H22A	1.3818	0.3499	0.6583	0.233*
H22B	1.4696	0.4191	0.6925	0.233*
H22C	1.4984	0.3575	0.6012	0.233*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0709 (14)	0.0801 (15)	0.0448 (12)	−0.0157 (12)	0.0088 (11)	0.0000 (10)
O1	0.0823 (13)	0.0837 (13)	0.0582 (11)	−0.0070 (10)	0.0055 (10)	0.0034 (10)
C9	0.0660 (16)	0.0682 (17)	0.0454 (14)	−0.0081 (13)	0.0138 (12)	0.0001 (13)
C8	0.0888 (19)	0.0678 (18)	0.0499 (16)	−0.0088 (15)	0.0131 (14)	−0.0086 (13)
C1	0.089 (2)	0.0510 (15)	0.0502 (16)	0.0035 (14)	0.0212 (15)	0.0016 (12)
C15	0.0668 (16)	0.0706 (17)	0.0416 (13)	−0.0087 (14)	0.0111 (12)	0.0006 (12)
C7	0.0844 (19)	0.0645 (17)	0.0557 (17)	−0.0031 (14)	0.0122 (14)	0.0015 (13)
C12	0.0649 (16)	0.0737 (19)	0.0482 (15)	−0.0078 (14)	0.0129 (13)	0.0067 (14)
C6	0.0709 (17)	0.0708 (17)	0.0506 (16)	−0.0037 (13)	0.0100 (14)	−0.0025 (13)
N1	0.122 (2)	0.0627 (15)	0.0669 (18)	0.0024 (15)	0.0329 (18)	0.0051 (13)
C5	0.0676 (17)	0.0603 (15)	0.0456 (14)	−0.0015 (13)	0.0145 (13)	−0.0012 (12)
C17	0.0784 (18)	0.081 (2)	0.0578 (16)	−0.0091 (15)	0.0283 (14)	−0.0113 (14)
C10	0.0750 (18)	0.0654 (17)	0.0573 (17)	−0.0058 (14)	0.0140 (14)	−0.0075 (13)
C3	0.0780 (19)	0.0664 (17)	0.0628 (18)	−0.0064 (14)	0.0192 (15)	0.0030 (13)
C4	0.0759 (19)	0.0733 (18)	0.0509 (15)	−0.0048 (14)	0.0110 (13)	0.0032 (13)
C19	0.096 (2)	0.0728 (18)	0.0534 (16)	−0.0129 (16)	0.0213 (15)	−0.0118 (13)
C20	0.0671 (18)	0.081 (2)	0.0609 (17)	−0.0175 (15)	0.0143 (14)	0.0071 (15)
O4	0.149 (2)	0.0996 (17)	0.0863 (16)	−0.0303 (16)	0.0442 (16)	0.0067 (12)
C2	0.089 (2)	0.0679 (17)	0.0475 (15)	0.0074 (15)	0.0095 (14)	0.0005 (13)
O2	0.1123 (17)	0.1195 (19)	0.1136 (19)	−0.0450 (16)	0.0391 (15)	−0.0177 (15)
C11	0.0712 (17)	0.0653 (17)	0.0660 (17)	−0.0010 (14)	0.0148 (14)	0.0018 (14)
O3	0.142 (2)	0.1228 (19)	0.0680 (15)	0.0173 (16)	0.0181 (15)	0.0345 (13)
C18	0.0690 (18)	0.090 (2)	0.0643 (17)	0.0004 (16)	0.0228 (14)	−0.0049 (15)
C16	0.0748 (17)	0.0720 (18)	0.0555 (15)	−0.0003 (15)	0.0197 (14)	−0.0019 (13)
C13	0.108 (2)	0.092 (2)	0.0624 (19)	−0.0062 (19)	0.0113 (17)	−0.0076 (17)
C14	0.092 (2)	0.131 (3)	0.067 (2)	−0.009 (2)	−0.0090 (17)	−0.0045 (19)
C21	0.128 (3)	0.088 (3)	0.159 (4)	−0.029 (2)	0.035 (3)	−0.046 (3)
C22	0.112 (3)	0.218 (5)	0.118 (4)	0.022 (3)	0.008 (3)	−0.046 (4)

Geometric parameters (Å, º) top

N2—C5	1.378 (3)	C10—H10	0.9300
N2—C9	1.439 (3)	C3—C4	1.373 (3)
N2—C15	1.439 (3)	C3—H3	0.9300
O1—C12	1.382 (3)	C4—H4	0.9300
O1—C13	1.399 (3)	C19—C20	1.377 (4)
C9—C7	1.375 (3)	C19—H19	0.9300
C9—C10	1.375 (3)	C20—C18	1.370 (4)
C8—C12	1.379 (4)	C20—O2	1.378 (3)
C8—C7	1.393 (4)	C2—H2	0.9300
C8—H8	0.9300	O2—C21	1.403 (4)
C1—C2	1.368 (4)	C11—H11	0.9300
C1—C3	1.373 (3)	C18—C16	1.359 (4)
C1—N1	1.449 (3)	C18—H18	0.9300
C15—C16	1.372 (3)	C16—H16	0.9300
C15—C17	1.379 (3)	C13—C14	1.496 (4)
C7—H7	0.9300	C13—H13A	0.9700
C12—C11	1.370 (3)	C13—H13B	0.9700
C6—C2	1.376 (4)	C14—H14A	0.9600
C6—C5	1.394 (3)	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
N1—O4	1.229 (3)	C21—C22	1.426 (5)
N1—O3	1.232 (3)	C21—H21A	0.9700
C5—C4	1.402 (3)	C21—H21B	0.9700
C17—C19	1.382 (3)	C22—H22A	0.9600
C17—H17	0.9300	C22—H22B	0.9600
C10—C11	1.374 (3)	C22—H22C	0.9600

C5—N2—C9	122.7 (2)	C20—C19—C17	119.7 (3)
C5—N2—C15	119.98 (19)	C20—C19—H19	120.2
C9—N2—C15	116.93 (19)	C17—C19—H19	120.2
C12—O1—C13	118.8 (2)	C18—C20—C19	119.8 (3)
C7—C9—C10	118.8 (2)	C18—C20—O2	116.3 (3)
C7—C9—N2	120.9 (2)	C19—C20—O2	123.9 (3)
C10—C9—N2	120.3 (2)	C1—C2—C6	120.0 (2)
C12—C8—C7	119.6 (2)	C1—C2—H2	120.0
C12—C8—H8	120.2	C6—C2—H2	120.0
C7—C8—H8	120.2	C20—O2—C21	120.0 (3)
C2—C1—C3	120.3 (2)	C12—C11—C10	120.4 (3)
C2—C1—N1	119.6 (3)	C12—C11—H11	119.8
C3—C1—N1	120.0 (3)	C10—C11—H11	119.8
C16—C15—C17	119.3 (2)	C16—C18—C20	120.4 (3)
C16—C15—N2	120.3 (2)	C16—C18—H18	119.8
C17—C15—N2	120.4 (2)	C20—C18—H18	119.8
C9—C7—C8	120.6 (3)	C18—C16—C15	120.8 (3)
C9—C7—H7	119.7	C18—C16—H16	119.6
C8—C7—H7	119.7	C15—C16—H16	119.6
C11—C12—C8	119.6 (2)	O1—C13—C14	108.4 (3)
C11—C12—O1	115.5 (2)	O1—C13—H13A	110.0
C8—C12—O1	124.9 (2)	C14—C13—H13A	110.0
C2—C6—C5	120.9 (3)	O1—C13—H13B	110.0
C2—C6—H6	119.5	C14—C13—H13B	110.0
C5—C6—H6	119.5	H13A—C13—H13B	108.4
O4—N1—O3	122.5 (3)	C13—C14—H14A	109.5
O4—N1—C1	118.4 (3)	C13—C14—H14B	109.5
O3—N1—C1	119.0 (3)	H14A—C14—H14B	109.5
N2—C5—C6	121.1 (2)	C13—C14—H14C	109.5
N2—C5—C4	121.0 (2)	H14A—C14—H14C	109.5
C6—C5—C4	117.9 (2)	H14B—C14—H14C	109.5
C15—C17—C19	120.1 (3)	O2—C21—C22	113.1 (3)
C15—C17—H17	120.0	O2—C21—H21A	109.0
C19—C17—H17	120.0	C22—C21—H21A	109.0
C11—C10—C9	120.9 (2)	O2—C21—H21B	109.0
C11—C10—H10	119.5	C22—C21—H21B	109.0
C9—C10—H10	119.5	H21A—C21—H21B	107.8
C1—C3—C4	120.3 (3)	C21—C22—H22A	109.5
C1—C3—H3	119.8	C21—C22—H22B	109.5
C4—C3—H3	119.8	H22A—C22—H22B	109.5
C3—C4—C5	120.4 (2)	C21—C22—H22C	109.5
C3—C4—H4	119.8	H22A—C22—H22C	109.5
C5—C4—H4	119.8	H22B—C22—H22C	109.5

C5—N2—C9—C7	−63.6 (3)	N2—C15—C17—C19	−177.9 (2)
C15—N2—C9—C7	124.0 (3)	C7—C9—C10—C11	2.2 (4)
C5—N2—C9—C10	118.2 (3)	N2—C9—C10—C11	−179.6 (2)
C15—N2—C9—C10	−54.2 (3)	C2—C1—C3—C4	−1.0 (4)
C5—N2—C15—C16	113.0 (3)	N1—C1—C3—C4	178.7 (2)
C9—N2—C15—C16	−74.3 (3)	C1—C3—C4—C5	−1.4 (4)
C5—N2—C15—C17	−69.5 (3)	N2—C5—C4—C3	−176.8 (2)
C9—N2—C15—C17	103.2 (3)	C6—C5—C4—C3	2.2 (4)
C10—C9—C7—C8	−2.8 (4)	C15—C17—C19—C20	0.3 (4)
N2—C9—C7—C8	179.0 (2)	C17—C19—C20—C18	−0.1 (4)
C12—C8—C7—C9	1.1 (4)	C17—C19—C20—O2	176.4 (2)
C7—C8—C12—C11	1.2 (4)	C3—C1—C2—C6	2.4 (4)
C7—C8—C12—O1	−178.5 (2)	N1—C1—C2—C6	−177.2 (2)
C13—O1—C12—C11	−176.0 (2)	C5—C6—C2—C1	−1.5 (4)
C13—O1—C12—C8	3.7 (4)	C18—C20—O2—C21	−154.8 (3)
C2—C1—N1—O4	175.8 (3)	C19—C20—O2—C21	28.6 (4)
C3—C1—N1—O4	−3.9 (4)	C8—C12—C11—C10	−1.8 (4)
C2—C1—N1—O3	−2.7 (4)	O1—C12—C11—C10	177.9 (2)
C3—C1—N1—O3	177.7 (2)	C9—C10—C11—C12	0.1 (4)
C9—N2—C5—C6	171.9 (2)	C19—C20—C18—C16	0.0 (4)
C15—N2—C5—C6	−15.9 (3)	O2—C20—C18—C16	−176.8 (2)
C9—N2—C5—C4	−9.1 (4)	C20—C18—C16—C15	0.0 (4)
C15—N2—C5—C4	163.1 (2)	C17—C15—C16—C18	0.3 (4)
C2—C6—C5—N2	178.2 (2)	N2—C15—C16—C18	177.8 (2)
C2—C6—C5—C4	−0.8 (4)	C12—O1—C13—C14	175.5 (2)
C16—C15—C17—C19	−0.4 (4)	C20—O2—C21—C22	79.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	0.93	2.56	3.371 (5)	146
C14—H14B···O4ⁱⁱ	0.96	2.55	3.458 (4)	158
C17—H17···Cg2ⁱⁱⁱ	0.93	2.78	3.700 (4)	173

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z; (iii) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	0.93	2.56	3.371 (5)	146
C14—H14B···O4ⁱⁱ	0.96	2.55	3.458 (4)	158
C17—H17···Cg2ⁱⁱⁱ	0.93	2.78	3.700 (4)	173

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z; (iii) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (grant No. KJ2010A030) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

References

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