9-Ethyl-3,6-bis­(1H-imidazol-1-yl)-9H-carbazole

Zhou, H.P.; Lv, L.F.; Wang, P.; Hu, R.T.

doi:10.1107/S1600536808013937

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1075

doi:10.1107/S1600536808013937

Open

access

9-Ethyl-3,6-bis(1H-imidazol-1-yl)-9H-carbazole

Hong Ping Zhou,^a ^* Liang Fei Lv,^a Peng Wang ^a and Ren Tao Hu ^a

^aDepartment of Chemistry, Anhui University, Hefei 230039, Peoples Republic of China and, Key Laboratory of Opto-Electronic Information Acquisition and, Manipulation (Anhui University), Ministry of Education, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 28 March 2008; accepted 9 May 2008; online 14 May 2008)

In the crystal structure of the title compound, C₂₀H₁₇N₅, the two imidazole rings are twisted with respect to the carbazole plane, making dihedral angles of 55.8 (2) and 43.7 (2)°. The crystal structure is stabilized by weak C—H⋯N and C—H⋯π interactions.

Related literature

For general background, see: Mi et al. (2003 ).

Experimental

Crystal data

C₂₀H₁₇N₅
M_r = 327.39
Triclinic, $[P \overline 1]$
a = 5.625 (2) Å
b = 8.826 (3) Å
c = 17.367 (6) Å
α = 92.698 (6)°
β = 96.011 (6)°
γ = 102.567 (6)°
V = 834.8 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.46 × 0.40 × 0.16 mm

Data collection

Bruker SMART APEX area-dectector diffractometer
Absorption correction: none
6040 measured reflections
2928 independent reflections
2611 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.120
S = 1.06
2928 reflections
225 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1ⁱ	0.93	2.73	3.533 (2)	144
C2—H2⋯N1ⁱⁱ	0.93	2.63	3.452 (2)	148
C16—H16⋯N5ⁱⁱ	0.93	2.68	3.509 (2)	149
C14—H14⋯N5ⁱⁱⁱ	0.93	2.66	3.570 (2)	165
Symmetry codes: (i) -x, -y, -z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013937/xu2412sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013937/xu2412Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives exhibit good charge transfer and hole transporting properties, which are being explored for a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs) (Mi et al., 2003). The title molecule containing imidazole with electrochemical and biology properties has been prepared, its crystal structure is reported here.

The molecular structure is shown in Fig. 1, the bond lengths and angles are normal. The dihedral angles between N2-imidazole and C4-benzene rings and between N4-imidazole and C10-benzene rings are 55.8 (2) and 43.7 (2)°, respectively. In the crystal structure, the molecules are stacked through the weak C19—H19A···Cgⁱ interactions (Cg is the centroid of the N1-imidazole ring), H19A···Cgⁱ = 2.85 Å, C19···Cgⁱ = 3.640 (11) Å and C19—H19A···Cgⁱ = 139° [symmetry code: (i) -1 + x, -1 + y, z]. The weak C—H···N hydrogen bonding (Table 1) helps to stabilize the crystal structure.

Related literature top

For general background, see: Mi et al. (2003).

Experimental top

For the preparation of 3,6-diimidazolyl-9-ethylcarbazole, a mixture of CuI (0.27 g, 1.40 mmol) and 1,10-phenanthroline (0.60 g, 3.00 mmol) were heated at 393 K with DMF (3 ml) as solvent for 10 min. Then, the mixture was cooled to room temperature, potassium tert-butanol (6.05 g, 54.00 mmol), imidazole (3.65 g, 54.00 mmol), 3,6-diiodo-9-ethylcarbazole (3.00 g, 6.70 mmol) and 18-crown-6 (litter) were added and heated at 413 k for 48 h, then the reaction mixture was heated to 433 k for 12 h, and cooled to room temperature. The mixture solution was poured into water and extracted by dichloromethane. The organic layer was separated, dried with anhydrous magnesium sulfate. Then it was filtered and concentrated, the re-crystallization from ethyl acetate produced light yellow single crystals (1.50 g, Yield 70.0%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids.

9-Ethyl-3,6-bis(1H-imidazol-1-yl)-9H-carbazole top

Crystal data top

C₂₀H₁₇N₅	Z = 2
M_r = 327.39	F(000) = 344
Triclinic, P1	D_x = 1.302 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.625 (2) Å	Cell parameters from 2928 reflections
b = 8.826 (3) Å	θ = 1.2–25.0°
c = 17.367 (6) Å	µ = 0.08 mm⁻¹
α = 92.698 (6)°	T = 293 K
β = 96.011 (6)°	Prism, yellow
γ = 102.567 (6)°	0.46 × 0.40 × 0.16 mm
V = 834.8 (5) Å³

Data collection top

Bruker SMART APEX area-dectector diffractometer	2611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 25.0°, θ_min = 1.2°
ϕ and ω scans	h = −6→6
6040 measured reflections	k = −10→10
2928 independent reflections	l = −20→20

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0695P)² + 0.1471P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2928 reflections	Δρ_max = 0.23 e Å⁻³
225 parameters	Δρ_min = −0.18 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: 0.044 (6)

Crystal data top

C₂₀H₁₇N₅	γ = 102.567 (6)°
M_r = 327.39	V = 834.8 (5) Å³
Triclinic, P1	Z = 2
a = 5.625 (2) Å	Mo Kα radiation
b = 8.826 (3) Å	µ = 0.08 mm⁻¹
c = 17.367 (6) Å	T = 293 K
α = 92.698 (6)°	0.46 × 0.40 × 0.16 mm
β = 96.011 (6)°

Data collection top

Bruker SMART APEX area-dectector diffractometer	2611 reflections with I > 2σ(I)
6040 measured reflections	R_int = 0.017
2928 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
2928 reflections	Δρ_min = −0.18 e Å⁻³
225 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.

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

	x	y	z	U_iso*/U_eq
N2	0.49085 (19)	0.34017 (13)	0.10310 (6)	0.0435 (3)
N4	0.89546 (19)	0.72250 (13)	0.53896 (6)	0.0418 (3)
N5	0.6235 (2)	0.67394 (15)	0.62354 (7)	0.0553 (4)
N1	0.1184 (2)	0.19639 (15)	0.06703 (7)	0.0535 (3)
N3	1.2016 (2)	0.83688 (14)	0.24918 (7)	0.0484 (3)
C13	0.9898 (2)	0.75062 (15)	0.46637 (7)	0.0405 (3)
C5	0.8279 (3)	0.56084 (17)	0.09187 (8)	0.0485 (4)
H5	0.8010	0.5396	0.0383	0.058*
C9	0.7148 (2)	0.49327 (16)	0.21905 (7)	0.0432 (3)
H9	0.6179	0.4289	0.2500	0.052*
C12	1.1789 (2)	0.88178 (16)	0.46167 (8)	0.0459 (4)
H12	1.2463	0.9456	0.5062	0.055*
C7	1.0438 (2)	0.71535 (16)	0.20364 (8)	0.0438 (3)
C10	1.1590 (2)	0.82136 (16)	0.32594 (8)	0.0433 (3)
C11	1.2661 (2)	0.91729 (16)	0.39191 (8)	0.0476 (4)
H11	1.3933	1.0032	0.3890	0.057*
C8	0.8970 (2)	0.62019 (15)	0.25193 (7)	0.0416 (3)
C14	0.8859 (2)	0.65280 (15)	0.40123 (7)	0.0430 (3)
H14	0.7624	0.5652	0.4048	0.052*
C2	0.5129 (3)	0.22459 (17)	0.05004 (8)	0.0493 (4)
H2	0.6569	0.2093	0.0323	0.059*
C18	0.6561 (2)	0.68650 (16)	0.55011 (8)	0.0480 (4)
H18	0.5281	0.6722	0.5101	0.058*
C15	0.9703 (2)	0.68841 (15)	0.33029 (7)	0.0416 (3)
C1	0.2852 (3)	0.13828 (17)	0.02886 (8)	0.0515 (4)
H1	0.2460	0.0517	−0.0065	0.062*
C6	1.0107 (3)	0.68540 (17)	0.12343 (8)	0.0496 (4)
H6	1.1090	0.7476	0.0920	0.060*
C4	0.6822 (2)	0.46580 (16)	0.13922 (7)	0.0423 (3)
C16	1.0248 (3)	0.73427 (18)	0.61152 (8)	0.0503 (4)
H16	1.1944	0.7584	0.6235	0.060*
C19	1.3664 (3)	0.96821 (17)	0.22027 (9)	0.0535 (4)
H19A	1.3862	1.0591	0.2560	0.064*
H19B	1.2921	0.9914	0.1705	0.064*
C3	0.2492 (2)	0.31619 (17)	0.11053 (8)	0.0473 (4)
H3	0.1832	0.3784	0.1432	0.057*
C17	0.8562 (3)	0.70373 (19)	0.66187 (8)	0.0553 (4)
H17	0.8929	0.7030	0.7153	0.066*
C20	1.6114 (4)	0.9380 (3)	0.21097 (14)	0.0896 (6)
H20A	1.6872	0.9167	0.2602	0.134*
H20B	1.7120	1.0279	0.1923	0.134*
H20C	1.5936	0.8501	0.1744	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0408 (6)	0.0507 (7)	0.0374 (6)	0.0095 (5)	0.0013 (4)	−0.0020 (5)
N4	0.0403 (6)	0.0420 (6)	0.0403 (6)	0.0042 (5)	0.0040 (5)	−0.0012 (5)
N5	0.0514 (7)	0.0583 (8)	0.0555 (8)	0.0067 (6)	0.0152 (6)	0.0044 (6)
N1	0.0427 (6)	0.0611 (8)	0.0533 (7)	0.0076 (6)	0.0006 (5)	0.0001 (6)
N3	0.0488 (7)	0.0466 (7)	0.0447 (7)	−0.0022 (5)	0.0084 (5)	0.0065 (5)
C13	0.0394 (7)	0.0409 (7)	0.0390 (7)	0.0047 (5)	0.0032 (5)	0.0012 (5)
C5	0.0521 (8)	0.0574 (9)	0.0353 (7)	0.0114 (7)	0.0047 (6)	0.0030 (6)
C9	0.0449 (7)	0.0436 (7)	0.0383 (7)	0.0042 (6)	0.0046 (5)	0.0022 (5)
C12	0.0446 (7)	0.0426 (8)	0.0448 (8)	0.0011 (6)	0.0003 (6)	−0.0031 (6)
C7	0.0438 (7)	0.0449 (8)	0.0416 (7)	0.0066 (6)	0.0056 (5)	0.0053 (6)
C10	0.0418 (7)	0.0415 (7)	0.0441 (7)	0.0032 (6)	0.0052 (5)	0.0050 (6)
C11	0.0429 (7)	0.0419 (8)	0.0508 (8)	−0.0048 (6)	0.0032 (6)	0.0029 (6)
C8	0.0433 (7)	0.0413 (7)	0.0380 (7)	0.0044 (6)	0.0051 (5)	0.0040 (5)
C14	0.0431 (7)	0.0388 (7)	0.0423 (7)	−0.0003 (6)	0.0040 (6)	0.0016 (6)
C2	0.0449 (8)	0.0552 (9)	0.0468 (8)	0.0118 (6)	0.0047 (6)	−0.0083 (6)
C18	0.0394 (7)	0.0499 (8)	0.0505 (8)	0.0019 (6)	0.0051 (6)	−0.0001 (6)
C15	0.0424 (7)	0.0381 (7)	0.0407 (7)	0.0015 (6)	0.0034 (5)	0.0035 (5)
C1	0.0513 (8)	0.0511 (8)	0.0483 (8)	0.0082 (7)	−0.0004 (6)	−0.0066 (6)
C6	0.0501 (8)	0.0552 (9)	0.0423 (8)	0.0051 (7)	0.0107 (6)	0.0101 (6)
C4	0.0397 (7)	0.0461 (8)	0.0400 (7)	0.0090 (6)	0.0017 (5)	−0.0001 (6)
C16	0.0441 (7)	0.0650 (9)	0.0411 (8)	0.0121 (6)	0.0021 (6)	0.0021 (6)
C19	0.0554 (9)	0.0474 (8)	0.0565 (9)	0.0047 (7)	0.0124 (7)	0.0122 (7)
C3	0.0406 (7)	0.0574 (9)	0.0442 (7)	0.0124 (6)	0.0045 (6)	0.0001 (6)
C17	0.0595 (9)	0.0679 (10)	0.0404 (8)	0.0165 (7)	0.0082 (6)	0.0074 (7)
C20	0.0618 (11)	0.0954 (15)	0.1158 (18)	0.0141 (10)	0.0283 (11)	0.0259 (13)

Geometric parameters (Å, º) top

N2—C3	1.3501 (17)	C7—C6	1.391 (2)
N2—C2	1.3769 (18)	C7—C8	1.4142 (18)
N2—C4	1.4336 (18)	C10—C11	1.3909 (19)
N4—C18	1.3512 (18)	C10—C15	1.4116 (19)
N4—C16	1.3750 (18)	C11—H11	0.9300
N4—C13	1.4299 (17)	C8—C15	1.4428 (19)
N5—C18	1.3135 (19)	C14—C15	1.3913 (19)
N5—C17	1.370 (2)	C14—H14	0.9300
N1—C3	1.3039 (18)	C2—C1	1.344 (2)
N1—C1	1.3748 (19)	C2—H2	0.9300
N3—C7	1.3867 (18)	C18—H18	0.9300
N3—C10	1.3867 (18)	C1—H1	0.9300
N3—C19	1.4629 (18)	C6—H6	0.9300
C13—C14	1.3844 (18)	C16—C17	1.350 (2)
C13—C12	1.403 (2)	C16—H16	0.9300
C5—C6	1.378 (2)	C19—C20	1.483 (2)
C5—C4	1.400 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C9—C4	1.3820 (19)	C3—H3	0.9300
C9—C8	1.3960 (18)	C17—H17	0.9300
C9—H9	0.9300	C20—H20A	0.9600
C12—C11	1.378 (2)	C20—H20B	0.9600
C12—H12	0.9300	C20—H20C	0.9600

C3—N2—C2	105.71 (11)	C1—C2—H2	126.8
C3—N2—C4	127.00 (11)	N2—C2—H2	126.8
C2—N2—C4	127.18 (11)	N5—C18—N4	112.78 (12)
C18—N4—C16	105.83 (11)	N5—C18—H18	123.6
C18—N4—C13	126.09 (11)	N4—C18—H18	123.6
C16—N4—C13	128.00 (11)	C14—C15—C10	119.99 (12)
C18—N5—C17	104.42 (12)	C14—C15—C8	133.50 (12)
C3—N1—C1	104.81 (11)	C10—C15—C8	106.43 (12)
C7—N3—C10	108.52 (11)	C2—C1—N1	110.27 (13)
C7—N3—C19	125.61 (12)	C2—C1—H1	124.9
C10—N3—C19	125.58 (12)	N1—C1—H1	124.9
C14—C13—C12	121.06 (12)	C5—C6—C7	118.08 (13)
C14—C13—N4	119.69 (12)	C5—C6—H6	121.0
C12—C13—N4	119.18 (11)	C7—C6—H6	121.0
C6—C5—C4	120.98 (13)	C9—C4—C5	121.53 (13)
C6—C5—H5	119.5	C9—C4—N2	119.89 (12)
C4—C5—H5	119.5	C5—C4—N2	118.56 (12)
C4—C9—C8	118.25 (13)	C17—C16—N4	106.22 (13)
C4—C9—H9	120.9	C17—C16—H16	126.9
C8—C9—H9	120.9	N4—C16—H16	126.9
C11—C12—C13	120.91 (12)	N3—C19—C20	112.98 (14)
C11—C12—H12	119.5	N3—C19—H19A	109.0
C13—C12—H12	119.5	C20—C19—H19A	109.0
N3—C7—C6	129.66 (13)	N3—C19—H19B	109.0
N3—C7—C8	108.93 (12)	C20—C19—H19B	109.0
C6—C7—C8	121.33 (13)	H19A—C19—H19B	107.8
N3—C10—C11	129.53 (13)	N1—C3—N2	112.77 (12)
N3—C10—C15	109.31 (12)	N1—C3—H3	123.6
C11—C10—C15	121.11 (13)	N2—C3—H3	123.6
C12—C11—C10	118.32 (13)	C16—C17—N5	110.75 (13)
C12—C11—H11	120.8	C16—C17—H17	124.6
C10—C11—H11	120.8	N5—C17—H17	124.6
C9—C8—C7	119.82 (12)	C19—C20—H20A	109.5
C9—C8—C15	133.27 (12)	C19—C20—H20B	109.5
C7—C8—C15	106.82 (12)	H20A—C20—H20B	109.5
C13—C14—C15	118.58 (12)	C19—C20—H20C	109.5
C13—C14—H14	120.7	H20A—C20—H20C	109.5
C15—C14—H14	120.7	H20B—C20—H20C	109.5
C1—C2—N2	106.44 (12)

C18—N4—C13—C14	−44.43 (19)	C13—C14—C15—C8	−175.75 (14)
C16—N4—C13—C14	139.43 (14)	N3—C10—C15—C14	−176.74 (11)
C18—N4—C13—C12	132.48 (14)	C11—C10—C15—C14	1.0 (2)
C16—N4—C13—C12	−43.66 (19)	N3—C10—C15—C8	0.35 (15)
C14—C13—C12—C11	0.2 (2)	C11—C10—C15—C8	178.06 (12)
N4—C13—C12—C11	−176.63 (11)	C9—C8—C15—C14	−0.2 (3)
C10—N3—C7—C6	176.82 (13)	C7—C8—C15—C14	176.22 (14)
C19—N3—C7—C6	2.8 (2)	C9—C8—C15—C10	−176.67 (14)
C10—N3—C7—C8	0.07 (15)	C7—C8—C15—C10	−0.30 (15)
C19—N3—C7—C8	−173.96 (13)	N2—C2—C1—N1	0.16 (17)
C7—N3—C10—C11	−177.73 (13)	C3—N1—C1—C2	−0.17 (17)
C19—N3—C10—C11	−3.7 (2)	C4—C5—C6—C7	−0.9 (2)
C7—N3—C10—C15	−0.26 (16)	N3—C7—C6—C5	−175.61 (13)
C19—N3—C10—C15	173.77 (13)	C8—C7—C6—C5	0.8 (2)
C13—C12—C11—C10	1.1 (2)	C8—C9—C4—C5	0.6 (2)
N3—C10—C11—C12	175.49 (13)	C8—C9—C4—N2	−177.63 (11)
C15—C10—C11—C12	−1.7 (2)	C6—C5—C4—C9	0.3 (2)
C4—C9—C8—C7	−0.7 (2)	C6—C5—C4—N2	178.49 (12)
C4—C9—C8—C15	175.30 (14)	C3—N2—C4—C9	55.86 (19)
N3—C7—C8—C9	177.10 (12)	C2—N2—C4—C9	−128.49 (15)
C6—C7—C8—C9	0.0 (2)	C3—N2—C4—C5	−122.38 (15)
N3—C7—C8—C15	0.15 (15)	C2—N2—C4—C5	53.27 (19)
C6—C7—C8—C15	−176.93 (13)	C18—N4—C16—C17	0.40 (16)
C12—C13—C14—C15	−1.0 (2)	C13—N4—C16—C17	177.15 (13)
N4—C13—C14—C15	175.86 (11)	C7—N3—C19—C20	−89.67 (19)
C3—N2—C2—C1	−0.09 (16)	C10—N3—C19—C20	97.30 (19)
C4—N2—C2—C1	−176.48 (13)	C1—N1—C3—N2	0.11 (16)
C17—N5—C18—N4	0.02 (16)	C2—N2—C3—N1	−0.02 (16)
C16—N4—C18—N5	−0.26 (16)	C4—N2—C3—N1	176.39 (12)
C13—N4—C18—N5	−177.10 (12)	N4—C16—C17—N5	−0.41 (18)
C13—C14—C15—C10	0.4 (2)	C18—N5—C17—C16	0.24 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ⁱ	0.93	2.73	3.533 (2)	144
C2—H2···N1ⁱⁱ	0.93	2.63	3.452 (2)	148
C16—H16···N5ⁱⁱ	0.93	2.68	3.509 (2)	149
C14—H14···N5ⁱⁱⁱ	0.93	2.66	3.570 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₅
M_r	327.39
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.625 (2), 8.826 (3), 17.367 (6)
α, β, γ (°)	92.698 (6), 96.011 (6), 102.567 (6)
V (Å³)	834.8 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.46 × 0.40 × 0.16

Data collection
Diffractometer	Bruker SMART APEX area-dectector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6040, 2928, 2611
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.120, 1.06
No. of reflections	2928
No. of parameters	225
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ⁱ	0.93	2.73	3.533 (2)	144.4
C2—H2···N1ⁱⁱ	0.93	2.63	3.452 (2)	147.5
C16—H16···N5ⁱⁱ	0.93	2.68	3.509 (2)	149.4
C14—H14···N5ⁱⁱⁱ	0.93	2.66	3.570 (2)	165.0

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (50532030, 50703001 and 20771001), the Natural Science Foundation of Anhui Province, China (070414188), the Doctoral Program Foundation of the Ministry of Education of China, the Education Committee of Anhui Province, China (2006K J032A), the Team for Scientific Innovation Foundation of Anhui Province (2006K J007TD), the Young Teacher Foundation of Institutions of Higher Education of Anhui Province (2007jq1019), the Ministry of Education and the Persons with Ability Foundation of Anhui University, China.

References

Bruker (2002). SMART and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Mi, B. X., Wang, P. F., Liu, M. W., Kwong, H. L., Wong, N. B., Lee, C. S. & Lee, S. T. (2003). Chem. Mater. 15, 3148–3151. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar