1,4-Dibut­oxy-2,5-bis­{(Z)-2-[4-(9H-carbazol-9-yl)phen­yl]ethen­yl}benzene

Fei, W.-W.; Li, R.; Wang, Z.-Y.; Wu, J.-Y.

doi:10.1107/S1600536812000414

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o321

doi:10.1107/S1600536812000414

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1,4-Dibutoxy-2,5-bis{(Z)-2-[4-(9H-carbazol-9-yl)phenyl]ethenyl}benzene

Wen-Wen Fei,^a Rui Li,^a Zhen-Yu Wang ^a and Jie-Ying Wu ^a ^*

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

(Received 19 December 2011; accepted 5 January 2012; online 11 January 2012)

The title compound, C₅₄H₄₈N₂O₂, lies about an inversion centre. The carbazole ring system makes dihedral angles of 58.43 (7) and 88.96 (7)°, respectively, with the adjacent and central benzene rings. The dihedral angle between the two benzene rings is 52.01 (8)°. In the crystal, molecules are linked by pairs of C—H⋯O interactions, forming a tape along the a axis. The methyl group is disordered over two sets of sites with occupancies of 0.63 (3) and 0.37 (3).

Related literature

For the crystal structures of related carbazole derivatives, see: Liu et al. (2007 ); Piotr (2011 ); Paital et al. (2007 ); Zhang et al. (2010 ). For applications of carbazole derivatives, see: Ravindranath (2007 ); Sun et al. (2011 ); Zhao et al. (2008 ).

Experimental

Crystal data

C₅₄H₄₈N₂O₂
M_r = 756.94
Monoclinic, P 2₁ /c
a = 8.437 (5) Å
b = 13.229 (5) Å
c = 19.165 (5) Å
β = 98.683 (5)°
V = 2114.5 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.986
8735 measured reflections
3713 independent reflections
2969 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.153
S = 1.03
3713 reflections
274 parameters
32 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24B⋯O1ⁱ	0.97	2.52	3.309 (4)	138
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000414/is5035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000414/is5035Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000414/is5035Isup3.cml

checkCIF report

Comment top

Recently, carbazole-based materials have been investigated for their high electrical and nonlinear optical properties (Ravindranath et al., 2007; Sun et al., 2011; Zhao et al., 2008). The introduction about the structure of carbazole derivatives has been reported (Paital et al., 2007; Piotr et al., 2011). In the title molecule (Fig. 1), which is centrosymmetric, there are two 9-phenyl-9H-carbazole rings and a central benzene ring. In the crystal structure, the neighboring molecules are connected through weak intermolecular C—H···O interactions.

Related literature top

For the crystal structures of related carbazole derivatives, see: Liu et al. (2007); Piotr (2011); Paital et al. (2007); Zhang et al. (2010). For applications of carbazole derivatives, see: Ravindranath (2007); Sun et al. (2011); Zhao et al. (2008).

Experimental top

4-(9H-Carbazol-9-yl)benzaldehyde (0.30 g, 1.1 mmol), 2,5-dibutoxy-1,4-bis(triphenylphosphonium)benzene dichloride (0.42 g, 0. 5 mmol) and tert-BuOK (0.34 g, 3 mmol) were added to a mortar with grinding fully. The reaction residue was extracted with 200 ml of dichloromethane, washed four times with distilled water, and dried with anhydrous MgSO₄. Then it was filtered and concentrated, purified by flash column-chromatography on silica. Elution with petroleum/ethyl acetate (50:1) gave the yellow powders (yield 69%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007; 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, showing 30% probability displacement ellipsoids.

1,4-Dibutoxy-2,5-bis{(Z)-2-[4-(9H-carbazol- 9-yl)phenyl]ethenyl}benzene top

Crystal data top

C₅₄H₄₈N₂O₂	F(000) = 804
M_r = 756.94	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3679 reflections
a = 8.437 (5) Å	θ = 2.4–27.0°
b = 13.229 (5) Å	µ = 0.07 mm⁻¹
c = 19.165 (5) Å	T = 293 K
β = 98.683 (5)°	Needle, yellow
V = 2114.5 (16) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3713 independent reflections
Radiation source: fine-focus sealed tube	2969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.979, T_max = 0.986	k = −15→15
8735 measured reflections	l = −22→18

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0789P)² + 0.6687P] where P = (F_o² + 2F_c²)/3
3713 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.44 e Å⁻³
32 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₅₄H₄₈N₂O₂	V = 2114.5 (16) Å³
M_r = 756.94	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.437 (5) Å	µ = 0.07 mm⁻¹
b = 13.229 (5) Å	T = 293 K
c = 19.165 (5) Å	0.30 × 0.20 × 0.20 mm
β = 98.683 (5)°

Data collection top

Bruker SMART APEX diffractometer	3713 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2969 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.020
8735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	32 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
3713 reflections	Δρ_min = −0.31 e Å⁻³
274 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	Occ. (<1)
C1	0.6314 (2)	0.01846 (14)	0.30709 (10)	0.0518 (5)
C2	0.5261 (3)	0.09216 (18)	0.27681 (12)	0.0650 (6)
H2	0.5617	0.1571	0.2689	0.078*
C3	0.3666 (3)	0.0660 (2)	0.25877 (14)	0.0804 (7)
H3	0.2937	0.1146	0.2390	0.096*
C4	0.3127 (3)	−0.0308 (2)	0.26946 (15)	0.0855 (8)
H4	0.2048	−0.0463	0.2562	0.103*
C5	0.4158 (3)	−0.1037 (2)	0.29922 (13)	0.0761 (7)
H5	0.3785	−0.1685	0.3063	0.091*
C6	0.5790 (3)	−0.08014 (16)	0.31913 (10)	0.0569 (5)
C7	0.7160 (3)	−0.13494 (14)	0.35341 (10)	0.0560 (5)
C8	0.7409 (4)	−0.23444 (16)	0.37736 (12)	0.0703 (7)
H8	0.6563	−0.2802	0.3724	0.084*
C9	0.8896 (4)	−0.26362 (17)	0.40789 (12)	0.0774 (8)
H9	0.9059	−0.3297	0.4239	0.093*
C10	1.0173 (4)	−0.19693 (18)	0.41564 (11)	0.0735 (7)
H10	1.1178	−0.2192	0.4367	0.088*
C11	0.9989 (3)	−0.09695 (16)	0.39257 (10)	0.0599 (5)
H11	1.0847	−0.0521	0.3976	0.072*
C12	0.8465 (3)	−0.06768 (14)	0.36177 (9)	0.0504 (5)
C13	0.8898 (2)	0.11459 (13)	0.33371 (9)	0.0459 (4)
C14	0.9683 (2)	0.15220 (14)	0.39700 (9)	0.0487 (5)
H14	0.9623	0.1178	0.4389	0.058*
C15	0.9041 (2)	0.16441 (15)	0.27167 (10)	0.0529 (5)
H15	0.8548	0.1384	0.2288	0.064*
C16	0.9915 (2)	0.25288 (14)	0.27323 (9)	0.0510 (5)
H16	1.0006	0.2857	0.2311	0.061*
C17	1.0551 (2)	0.24032 (14)	0.39810 (9)	0.0477 (5)
H17	1.1077	0.2646	0.4410	0.057*
C18	1.0662 (2)	0.29390 (13)	0.33655 (9)	0.0426 (4)
C19	1.1556 (2)	0.38949 (14)	0.33594 (9)	0.0490 (5)
H19	1.2118	0.3978	0.2982	0.059*
C20	1.1673 (2)	0.46543 (14)	0.38176 (10)	0.0497 (5)
H20	1.2394	0.5161	0.3745	0.060*
C21	1.0817 (2)	0.48059 (12)	0.44267 (9)	0.0432 (4)
C22	0.9217 (2)	0.45503 (13)	0.43986 (10)	0.0464 (4)
H22	0.8678	0.4248	0.3993	0.056*
C23	0.8406 (2)	0.47336 (14)	0.49562 (10)	0.0492 (5)
C24	0.5859 (3)	0.4184 (3)	0.43144 (16)	0.0973 (10)
H24A	0.6265	0.4481	0.3914	0.117*
H24B	0.4763	0.4411	0.4305	0.117*
C25	0.5883 (4)	0.3084 (3)	0.42550 (18)	0.1024 (10)
H25A	0.6980	0.2858	0.4264	0.123*
H25B	0.5274	0.2883	0.3806	0.123*
C26	0.5189 (4)	0.2581 (3)	0.48432 (18)	0.1114 (11)
H26A	0.4070	0.2769	0.4817	0.134*	0.63 (3)
H26B	0.5754	0.2811	0.5294	0.134*	0.63 (3)
H26C	0.4259	0.2958	0.4938	0.134*	0.37 (3)
H26D	0.5976	0.2588	0.5268	0.134*	0.37 (3)
C27A	0.533 (2)	0.1370 (7)	0.4794 (7)	0.132 (5)	0.63 (3)
H27A	0.4529	0.1121	0.4426	0.198*	0.63 (3)
H27B	0.5179	0.1073	0.5236	0.198*	0.63 (3)
H27C	0.6376	0.1193	0.4690	0.198*	0.63 (3)
C27B	0.470 (3)	0.1500 (14)	0.4664 (14)	0.153 (8)	0.37 (3)
H27D	0.4231	0.1459	0.4176	0.230*	0.37 (3)
H27E	0.3938	0.1283	0.4956	0.230*	0.37 (3)
H27F	0.5632	0.1073	0.4745	0.230*	0.37 (3)
N1	0.7950 (2)	0.02509 (11)	0.33273 (8)	0.0504 (4)
O1	0.68197 (18)	0.45206 (16)	0.49568 (9)	0.0871 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0634 (12)	0.0469 (11)	0.0456 (10)	−0.0032 (9)	0.0100 (9)	−0.0028 (8)
C2	0.0711 (14)	0.0589 (13)	0.0640 (13)	0.0009 (11)	0.0070 (11)	0.0061 (10)
C3	0.0695 (15)	0.095 (2)	0.0752 (16)	0.0056 (14)	0.0056 (12)	0.0100 (14)
C4	0.0678 (15)	0.104 (2)	0.0837 (18)	−0.0165 (15)	0.0096 (13)	0.0063 (16)
C5	0.0846 (17)	0.0732 (16)	0.0732 (15)	−0.0259 (14)	0.0210 (13)	−0.0051 (13)
C6	0.0754 (14)	0.0500 (11)	0.0478 (10)	−0.0087 (10)	0.0177 (10)	−0.0043 (9)
C7	0.0882 (15)	0.0402 (10)	0.0438 (10)	−0.0057 (10)	0.0237 (10)	−0.0032 (8)
C8	0.116 (2)	0.0428 (12)	0.0564 (13)	−0.0053 (12)	0.0281 (13)	0.0017 (10)
C9	0.143 (3)	0.0413 (12)	0.0511 (12)	0.0125 (15)	0.0259 (14)	0.0067 (10)
C10	0.115 (2)	0.0589 (14)	0.0454 (11)	0.0290 (14)	0.0092 (12)	0.0029 (10)
C11	0.0848 (15)	0.0499 (12)	0.0441 (10)	0.0105 (11)	0.0071 (10)	−0.0027 (9)
C12	0.0774 (13)	0.0363 (10)	0.0385 (9)	0.0052 (9)	0.0122 (9)	−0.0012 (7)
C13	0.0582 (11)	0.0340 (9)	0.0455 (10)	0.0024 (8)	0.0084 (8)	−0.0016 (7)
C14	0.0693 (12)	0.0390 (10)	0.0381 (9)	0.0030 (9)	0.0095 (8)	0.0023 (7)
C15	0.0740 (13)	0.0453 (11)	0.0377 (9)	−0.0055 (9)	0.0029 (9)	−0.0057 (8)
C16	0.0727 (13)	0.0464 (11)	0.0350 (9)	−0.0033 (9)	0.0116 (9)	0.0009 (8)
C17	0.0627 (11)	0.0427 (10)	0.0361 (9)	0.0013 (9)	0.0026 (8)	−0.0040 (7)
C18	0.0502 (10)	0.0392 (9)	0.0398 (9)	0.0034 (8)	0.0111 (8)	−0.0030 (7)
C19	0.0568 (11)	0.0518 (11)	0.0397 (9)	−0.0054 (9)	0.0119 (8)	0.0003 (8)
C20	0.0573 (11)	0.0424 (10)	0.0497 (10)	−0.0099 (8)	0.0092 (9)	0.0016 (8)
C21	0.0541 (10)	0.0289 (9)	0.0456 (10)	0.0017 (7)	0.0039 (8)	0.0001 (7)
C22	0.0519 (10)	0.0389 (9)	0.0461 (10)	−0.0001 (8)	−0.0001 (8)	−0.0091 (8)
C23	0.0473 (10)	0.0431 (10)	0.0564 (11)	−0.0025 (8)	0.0051 (8)	−0.0098 (8)
C24	0.0584 (14)	0.132 (3)	0.100 (2)	−0.0136 (15)	0.0099 (13)	−0.0564 (19)
C25	0.0849 (18)	0.121 (3)	0.106 (2)	−0.0070 (17)	0.0279 (16)	−0.0361 (19)
C26	0.0852 (19)	0.157 (3)	0.099 (2)	−0.029 (2)	0.0365 (17)	−0.028 (2)
C27A	0.159 (10)	0.136 (7)	0.109 (6)	−0.076 (6)	0.044 (6)	−0.010 (5)
C27B	0.104 (11)	0.203 (15)	0.153 (13)	−0.004 (10)	0.019 (9)	−0.083 (11)
N1	0.0648 (10)	0.0354 (8)	0.0499 (9)	−0.0006 (7)	0.0048 (8)	0.0012 (7)
O1	0.0524 (9)	0.1291 (16)	0.0816 (11)	−0.0258 (9)	0.0161 (8)	−0.0559 (11)

Geometric parameters (Å, º) top

C1—C2	1.386 (3)	C17—C18	1.391 (2)
C1—N1	1.396 (3)	C17—H17	0.9300
C1—C6	1.408 (3)	C18—C19	1.473 (3)
C2—C3	1.383 (3)	C19—C20	1.328 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.384 (4)	C20—C21	1.476 (3)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.365 (4)	C21—C22	1.385 (3)
C4—H4	0.9300	C21—C23ⁱ	1.402 (3)
C5—C6	1.407 (3)	C22—C23	1.374 (3)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.437 (3)	C23—O1	1.368 (2)
C7—C8	1.399 (3)	C23—C21ⁱ	1.402 (3)
C7—C12	1.406 (3)	C24—O1	1.438 (3)
C8—C9	1.358 (4)	C24—C25	1.461 (5)
C8—H8	0.9300	C24—H24A	0.9700
C9—C10	1.383 (4)	C24—H24B	0.9700
C9—H9	0.9300	C25—C26	1.502 (4)
C10—C11	1.396 (3)	C25—H25A	0.9700
C10—H10	0.9300	C25—H25B	0.9700
C11—C12	1.387 (3)	C26—C27B	1.512 (16)
C11—H11	0.9300	C26—C27A	1.611 (11)
C12—N1	1.390 (2)	C26—H26A	0.9700
C13—C15	1.380 (3)	C26—H26B	0.9700
C13—C14	1.384 (3)	C26—H26C	0.9700
C13—N1	1.427 (2)	C26—H26D	0.9700
C14—C17	1.375 (3)	C27A—H27A	0.9600
C14—H14	0.9300	C27A—H27B	0.9600
C15—C16	1.381 (3)	C27A—H27C	0.9600
C15—H15	0.9300	C27B—H27D	0.9600
C16—C18	1.390 (3)	C27B—H27E	0.9600
C16—H16	0.9300	C27B—H27F	0.9600

C2—C1—N1	129.80 (18)	C17—C18—C19	122.95 (16)
C2—C1—C6	121.6 (2)	C20—C19—C18	129.11 (17)
N1—C1—C6	108.58 (17)	C20—C19—H19	115.4
C3—C2—C1	117.8 (2)	C18—C19—H19	115.4
C3—C2—H2	121.1	C19—C20—C21	129.00 (17)
C1—C2—H2	121.1	C19—C20—H20	115.5
C2—C3—C4	121.6 (3)	C21—C20—H20	115.5
C2—C3—H3	119.2	C22—C21—C23ⁱ	117.90 (17)
C4—C3—H3	119.2	C22—C21—C20	121.78 (16)
C5—C4—C3	120.8 (2)	C23ⁱ—C21—C20	120.25 (17)
C5—C4—H4	119.6	C23—C22—C21	121.55 (17)
C3—C4—H4	119.6	C23—C22—H22	119.2
C4—C5—C6	119.5 (2)	C21—C22—H22	119.2
C4—C5—H5	120.2	O1—C23—C22	124.48 (17)
C6—C5—H5	120.2	O1—C23—C21ⁱ	114.95 (17)
C5—C6—C1	118.6 (2)	C22—C23—C21ⁱ	120.55 (17)
C5—C6—C7	134.4 (2)	O1—C24—C25	111.3 (3)
C1—C6—C7	106.96 (18)	O1—C24—H24A	109.4
C8—C7—C12	118.8 (2)	C25—C24—H24A	109.4
C8—C7—C6	134.0 (2)	O1—C24—H24B	109.4
C12—C7—C6	107.15 (17)	C25—C24—H24B	109.4
C9—C8—C7	119.5 (2)	H24A—C24—H24B	108.0
C9—C8—H8	120.3	C24—C25—C26	111.8 (3)
C7—C8—H8	120.3	C24—C25—H25A	109.3
C8—C9—C10	121.3 (2)	C26—C25—H25A	109.3
C8—C9—H9	119.4	C24—C25—H25B	109.3
C10—C9—H9	119.4	C26—C25—H25B	109.3
C9—C10—C11	121.5 (2)	H25A—C25—H25B	107.9
C9—C10—H10	119.2	C25—C26—C27B	111.8 (10)
C11—C10—H10	119.2	C25—C26—C27A	110.8 (5)
C12—C11—C10	116.8 (2)	C25—C26—H26A	109.5
C12—C11—H11	121.6	C27A—C26—H26A	109.5
C10—C11—H11	121.6	C25—C26—H26B	109.5
C11—C12—N1	129.10 (19)	C27A—C26—H26B	109.5
C11—C12—C7	122.12 (19)	H26A—C26—H26B	108.1
N1—C12—C7	108.74 (18)	C25—C26—H26C	109.3
C15—C13—C14	119.39 (17)	C27B—C26—H26C	109.3
C15—C13—N1	120.42 (16)	C25—C26—H26D	109.3
C14—C13—N1	120.19 (16)	C27B—C26—H26D	109.2
C17—C14—C13	120.11 (17)	H26C—C26—H26D	107.9
C17—C14—H14	119.9	C26—C27A—H27A	109.5
C13—C14—H14	119.9	C26—C27A—H27B	109.5
C13—C15—C16	120.11 (17)	C26—C27A—H27C	109.5
C13—C15—H15	119.9	C26—C27B—H27D	109.5
C16—C15—H15	119.9	C26—C27B—H27E	109.5
C15—C16—C18	121.32 (17)	H27D—C27B—H27E	109.5
C15—C16—H16	119.3	C26—C27B—H27F	109.5
C18—C16—H16	119.3	H27D—C27B—H27F	109.5
C14—C17—C18	121.50 (16)	H27E—C27B—H27F	109.5
C14—C17—H17	119.2	C12—N1—C1	108.55 (16)
C18—C17—H17	119.2	C12—N1—C13	125.92 (17)
C16—C18—C17	117.49 (17)	C1—N1—C13	125.37 (15)
C16—C18—C19	119.55 (16)	C23—O1—C24	119.20 (18)

N1—C1—C2—C3	−177.0 (2)	C15—C16—C18—C17	2.6 (3)
C6—C1—C2—C3	0.2 (3)	C15—C16—C18—C19	−178.79 (18)
C1—C2—C3—C4	−0.9 (4)	C14—C17—C18—C16	−2.6 (3)
C2—C3—C4—C5	0.8 (4)	C14—C17—C18—C19	178.82 (17)
C3—C4—C5—C6	−0.1 (4)	C16—C18—C19—C20	143.1 (2)
C4—C5—C6—C1	−0.5 (3)	C17—C18—C19—C20	−38.4 (3)
C4—C5—C6—C7	177.0 (2)	C18—C19—C20—C21	−6.6 (3)
C2—C1—C6—C5	0.5 (3)	C19—C20—C21—C22	−38.6 (3)
N1—C1—C6—C5	178.24 (18)	C19—C20—C21—C23ⁱ	144.7 (2)
C2—C1—C6—C7	−177.64 (18)	C23ⁱ—C21—C22—C23	−0.4 (3)
N1—C1—C6—C7	0.1 (2)	C20—C21—C22—C23	−177.11 (17)
C5—C6—C7—C8	3.4 (4)	C21—C22—C23—O1	178.50 (19)
C1—C6—C7—C8	−178.8 (2)	C21—C22—C23—C21ⁱ	0.4 (3)
C5—C6—C7—C12	−177.1 (2)	O1—C24—C25—C26	62.0 (3)
C1—C6—C7—C12	0.6 (2)	C24—C25—C26—C27B	161.1 (12)
C12—C7—C8—C9	0.0 (3)	C24—C25—C26—C27A	−176.4 (8)
C6—C7—C8—C9	179.4 (2)	C11—C12—N1—C1	179.11 (18)
C7—C8—C9—C10	−0.2 (3)	C7—C12—N1—C1	1.2 (2)
C8—C9—C10—C11	0.1 (3)	C11—C12—N1—C13	−5.4 (3)
C9—C10—C11—C12	0.2 (3)	C7—C12—N1—C13	176.77 (16)
C10—C11—C12—N1	−178.08 (18)	C2—C1—N1—C12	176.7 (2)
C10—C11—C12—C7	−0.4 (3)	C6—C1—N1—C12	−0.8 (2)
C8—C7—C12—C11	0.4 (3)	C2—C1—N1—C13	1.1 (3)
C6—C7—C12—C11	−179.21 (17)	C6—C1—N1—C13	−176.38 (16)
C8—C7—C12—N1	178.43 (17)	C15—C13—N1—C12	125.6 (2)
C6—C7—C12—N1	−1.2 (2)	C14—C13—N1—C12	−54.4 (3)
C15—C13—C14—C17	2.2 (3)	C15—C13—N1—C1	−59.6 (3)
N1—C13—C14—C17	−177.80 (17)	C14—C13—N1—C1	120.4 (2)
C14—C13—C15—C16	−2.2 (3)	C22—C23—O1—C24	−7.1 (4)
N1—C13—C15—C16	177.77 (17)	C21ⁱ—C23—O1—C24	171.1 (2)
C13—C15—C16—C18	−0.2 (3)	C25—C24—O1—C23	90.2 (3)
C13—C14—C17—C18	0.3 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24B···O1ⁱⁱ	0.97	2.52	3.309 (4)	138

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₅₄H₄₈N₂O₂
M_r	756.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.437 (5), 13.229 (5), 19.165 (5)
β (°)	98.683 (5)
V (Å³)	2114.5 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	8735, 3713, 2969
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.153, 1.03
No. of reflections	3713
No. of parameters	274
No. of restraints	32
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.31

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24B···O1ⁱ	0.97	2.52	3.309 (4)	138

Symmetry code: (i) −x+1, −y+1, −z+1.

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 Graduate Students Academic Innovation Research Project of Anhui University (grant No. yqh090020).

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