6-Chloro-2-phenyl-3-(2-phenyl­ethyn­yl)quinoxaline

Ouyang, X.-L.; Ouyang, M.; Huang, S.-W.

doi:10.1107/S1600536812020776

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1741

doi:10.1107/S1600536812020776

Open

access

6-Chloro-2-phenyl-3-(2-phenylethynyl)quinoxaline

Xi-Lin Ouyang,^a Miao Ouyang ^b and Shi-Wen Huang ^a ^*

^aYoujiang Medical University for Nationalities, Baise, Guangxi 533000, People's Republic of China, and ^bDepartment of Chemistry and Life Science, Hechi University, Yizhou, Guangxi 546300, People's Republic of China
^*Correspondence e-mail: shi.wen.huang@163.com

(Received 18 April 2012; accepted 8 May 2012; online 16 May 2012)

In the title compound, C₂₂H₁₃ClN₂, the quinoxaline ring system is close to planar [maximum deviation = 0.061 (2) Å]. The phenyl ring at the 2-position and the phenyl ring of the phenylethynyl substituent make dihedral angles of 49.32 (7) and 11.99 (7) °, respectively, with the quinoxaline mean plane. The two phenyl rings are inclined to one another by 61.27 (9)°. In the crystal, molecules are linked by C—H⋯π and π–π interactions [centroid–centroid distances = 3.6210 (12) and 3.8091 (12) Å].

Related literature

For the biological activity of quinoxaline derivatives, see: Rodrigo et al. (2002 ); Watkins et al. (2009 ); Sashidhara et al. (2009 ). For the crystal structures of quinoxaline derivatives, see: Hegedus et al. (2003 ); Naraso et al. (2006 ); Hassan et al. (2010 ); Ammermann et al. (2008 ); Daouda et al. (2011 ); Ramli et al. (2012 ).

Experimental

Crystal data

C₂₂H₁₃ClN₂
M_r = 340.79
Triclinic, $[P \overline 1]$
a = 8.8652 (13) Å
b = 9.8591 (8) Å
c = 10.9740 (17) Å
α = 73.032 (15)°
β = 81.036 (17)°
γ = 64.374 (13)°
V = 826.68 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 223 K
0.70 × 0.45 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.649, T_max = 0.954
7504 measured reflections
3714 independent reflections
2855 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.128
S = 1.07
3714 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg2ⁱ	0.94	3.00	3.845 (2)	151
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2002 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2002); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020776/su2414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020776/su2414Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020776/su2414Isup3.cml

checkCIF report

Comment top

The design of small molecular weight compounds has aroused much interest in the past decades due to the advances in targeted therapeutics coupled with novel techniques in target identification. It is well know that quinoxalines have broad applications in the fields of medicine and pharmaceuticals. It has been shown that many quinoxaline derivatives exhibit good biological activities, such as antituberculous activities (Rodrigo et al., 2002), antioxidative properties (Watkins et al., 2009), and antidyslipidemic (Sashidhara et al., 2009). Recently, a large number of crystal structures of quinoxaline derivatives have been reported (Hegedus et al., 2003; Naraso et al., 2006; Hassan et al., 2010; Ammermann et al., 2008; Daouda et al., 2011; Ramli et al., 2012).

In the title compound (Fig. 1) the phenyl ring of the phenylethynyl substituent is twisted by 11.99 (7)° out of the mean plane of the quinoxaline fused-ring system [planar to within 0.061 (2) Å]. The phenyl ring of the substituent at the 2-position, C7, makes dihedral angles of 49.32 (7)° and 61.27 (9)°, respectively, with the quinoxaline mean plane and the phenylethynyl phenyl ring.

In the crystal (Fig. 2), molecules are linked by C—H···π interactions involving the phenylethynyl phenyl ring (Table 1), and by π–π interactions involving inversion related quinoxaline rings and the phenylethynyl phenyl ring [Cg1···Cg1ⁱ 3.6210 (12) Å, interplanar spacing of 3.3635 (7) Å, slippage of 1.341 Å; Cg1···Cg2ⁱⁱ 3.8091 (12) Å; Cg1 is the centroid of the C1-C6 ring; Cg2 is the centroid of the C17-C22 ring; symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y, -z+2].

Footnote to Table 1: Cg2 is the centroid of the C17-C22 ring.

Related literature top

For the biological activity of quinoxaline derivatives, see: Rodrigo et al. (2002); Watkins et al. (2009); Sashidhara et al. (2009). For the crystal structures of quinoxaline derivatives, see: Hegedus et al. (2003); Naraso et al. (2006); Hassan et al. (2010); Ammermann et al. (2008); Daouda et al. (2011); Ramli et al. (2012).

Experimental top

4-Chloro-1,2-diaminobenzene (2.5 mmol), CuCl (0.1 mmol), chlorobenzene (3 ml) and phenylethynylene(1 mmol) were added to a sealed tube and heated to 343 K by stirring. After the completion of the reaction (as monitored by TLC), the inorganic material salt was filtered and the reaction mixture was extracted with EtOAc. The mixture was separated after washed by saturated NaCl solution, then the oily layer was dried by anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product obtained was purified by column chromatography (eluent: 50:1 Petroleum ether–EtOAc) to give the title compound. Block-like yellow crystals were obtained by slow evaporation of the solvents.

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule showing the atom-labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis.

6-Chloro-2-phenyl-3-(2-phenylethynyl)quinoxaline top

Crystal data top

C₂₂H₁₃ClN₂	Z = 2
M_r = 340.79	F(000) = 352
Triclinic, P1	D_x = 1.369 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 8.8652 (13) Å	Cell parameters from 3874 reflections
b = 9.8591 (8) Å	θ = 3.2–27.5°
c = 10.9740 (17) Å	µ = 0.24 mm⁻¹
α = 73.032 (15)°	T = 223 K
β = 81.036 (17)°	Block, yellow
γ = 64.374 (13)°	0.70 × 0.45 × 0.20 mm
V = 826.68 (19) Å³

Data collection top

Rigaku Saturn diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −11→9
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
T_min = 0.649, T_max = 0.954	l = −14→10
7504 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0712P)²] where P = (F_o² + 2F_c²)/3
3714 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₁₃ClN₂	γ = 64.374 (13)°
M_r = 340.79	V = 826.68 (19) Å³
Triclinic, P1	Z = 2
a = 8.8652 (13) Å	Mo Kα radiation
b = 9.8591 (8) Å	µ = 0.24 mm⁻¹
c = 10.9740 (17) Å	T = 223 K
α = 73.032 (15)°	0.70 × 0.45 × 0.20 mm
β = 81.036 (17)°

Data collection top

Rigaku Saturn diffractometer	3714 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2855 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.954	R_int = 0.024
7504 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
3714 reflections	Δρ_min = −0.37 e Å⁻³
227 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
Cl1	−0.11370 (6)	0.42900 (6)	1.28280 (4)	0.05093 (18)
N1	0.47258 (16)	0.32096 (14)	0.93213 (12)	0.0299 (3)
N2	0.26481 (16)	0.16607 (15)	0.94729 (12)	0.0314 (3)
C1	0.05364 (19)	0.40009 (19)	1.17229 (15)	0.0344 (4)
C2	0.1450 (2)	0.49110 (19)	1.15630 (15)	0.0349 (4)
H2	0.1121	0.5680	1.2012	0.042*
C3	0.28190 (19)	0.46636 (18)	1.07482 (15)	0.0326 (4)
H3	0.3446	0.5255	1.0643	0.039*
C4	0.32946 (18)	0.35241 (17)	1.00641 (14)	0.0286 (3)
C5	0.22960 (19)	0.26891 (18)	1.01856 (14)	0.0298 (3)
C6	0.0918 (2)	0.29202 (19)	1.10582 (15)	0.0338 (4)
H6	0.0276	0.2339	1.1178	0.041*
C7	0.51048 (19)	0.21689 (17)	0.86690 (14)	0.0292 (3)
C8	0.40000 (18)	0.14242 (17)	0.87130 (14)	0.0288 (3)
C9	0.67530 (19)	0.17448 (17)	0.79653 (15)	0.0308 (3)
C10	0.8145 (2)	0.14816 (19)	0.85823 (17)	0.0379 (4)
H10	0.8026	0.1569	0.9426	0.045*
C11	0.9711 (2)	0.1090 (2)	0.79661 (19)	0.0456 (5)
H11	1.0649	0.0899	0.8396	0.055*
C12	0.9889 (2)	0.0981 (2)	0.6723 (2)	0.0485 (5)
H12	1.0947	0.0714	0.6305	0.058*
C13	0.8506 (2)	0.1266 (2)	0.60934 (18)	0.0459 (5)
H13	0.8628	0.1209	0.5241	0.055*
C14	0.6945 (2)	0.16343 (19)	0.67054 (16)	0.0366 (4)
H14	0.6016	0.1810	0.6274	0.044*
C15	0.43695 (19)	0.03324 (18)	0.79721 (15)	0.0322 (4)
C16	0.4708 (2)	−0.06017 (18)	0.73719 (15)	0.0339 (4)
C17	0.5261 (2)	−0.17824 (18)	0.66936 (15)	0.0324 (4)
C18	0.6633 (2)	−0.1962 (2)	0.58335 (16)	0.0397 (4)
H18	0.7119	−0.1241	0.5638	0.048*
C19	0.7275 (2)	−0.3183 (2)	0.52727 (17)	0.0434 (4)
H19	0.8201	−0.3299	0.4699	0.052*
C20	0.6561 (2)	−0.4245 (2)	0.55506 (17)	0.0420 (4)
H20	0.7017	−0.5093	0.5179	0.050*
C21	0.5186 (2)	−0.4060 (2)	0.63702 (17)	0.0399 (4)
H21	0.4698	−0.4777	0.6547	0.048*
C22	0.4516 (2)	−0.28344 (19)	0.69351 (16)	0.0364 (4)
H22	0.3562	−0.2705	0.7481	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0412 (3)	0.0698 (3)	0.0470 (3)	−0.0267 (2)	0.0169 (2)	−0.0255 (2)
N1	0.0286 (6)	0.0311 (7)	0.0339 (7)	−0.0147 (6)	0.0008 (6)	−0.0106 (6)
N2	0.0298 (7)	0.0338 (7)	0.0353 (7)	−0.0166 (6)	−0.0003 (6)	−0.0103 (6)
C1	0.0287 (8)	0.0418 (9)	0.0311 (8)	−0.0133 (7)	0.0021 (7)	−0.0102 (7)
C2	0.0334 (8)	0.0378 (9)	0.0358 (9)	−0.0136 (7)	0.0004 (7)	−0.0151 (7)
C3	0.0332 (8)	0.0334 (8)	0.0358 (8)	−0.0158 (7)	−0.0027 (7)	−0.0112 (7)
C4	0.0255 (7)	0.0310 (8)	0.0307 (8)	−0.0131 (7)	−0.0008 (6)	−0.0075 (7)
C5	0.0287 (8)	0.0306 (8)	0.0309 (8)	−0.0127 (7)	−0.0032 (6)	−0.0070 (7)
C6	0.0306 (8)	0.0387 (9)	0.0356 (8)	−0.0181 (7)	0.0014 (7)	−0.0092 (7)
C7	0.0277 (8)	0.0296 (8)	0.0308 (8)	−0.0129 (6)	−0.0011 (6)	−0.0062 (6)
C8	0.0272 (7)	0.0281 (8)	0.0325 (8)	−0.0115 (6)	−0.0018 (7)	−0.0089 (7)
C9	0.0287 (8)	0.0277 (8)	0.0386 (8)	−0.0145 (7)	0.0044 (7)	−0.0100 (7)
C10	0.0348 (9)	0.0410 (9)	0.0446 (9)	−0.0194 (8)	0.0025 (8)	−0.0164 (8)
C11	0.0289 (8)	0.0484 (11)	0.0660 (12)	−0.0191 (8)	0.0024 (9)	−0.0207 (9)
C12	0.0356 (9)	0.0501 (11)	0.0656 (12)	−0.0230 (9)	0.0192 (9)	−0.0254 (10)
C13	0.0480 (10)	0.0495 (11)	0.0443 (10)	−0.0244 (9)	0.0154 (9)	−0.0195 (9)
C14	0.0358 (9)	0.0390 (9)	0.0380 (9)	−0.0177 (8)	0.0043 (7)	−0.0130 (7)
C15	0.0297 (8)	0.0339 (8)	0.0372 (9)	−0.0161 (7)	−0.0002 (7)	−0.0105 (7)
C16	0.0333 (8)	0.0340 (9)	0.0372 (9)	−0.0165 (7)	−0.0018 (7)	−0.0082 (7)
C17	0.0331 (8)	0.0313 (8)	0.0343 (8)	−0.0132 (7)	−0.0034 (7)	−0.0096 (7)
C18	0.0445 (10)	0.0375 (9)	0.0411 (9)	−0.0212 (8)	0.0023 (8)	−0.0107 (8)
C19	0.0442 (10)	0.0480 (10)	0.0386 (9)	−0.0195 (9)	0.0078 (8)	−0.0157 (8)
C20	0.0511 (10)	0.0369 (9)	0.0404 (9)	−0.0144 (8)	−0.0025 (8)	−0.0182 (8)
C21	0.0454 (10)	0.0386 (9)	0.0447 (10)	−0.0219 (8)	−0.0052 (8)	−0.0140 (8)
C22	0.0357 (9)	0.0385 (9)	0.0406 (9)	−0.0177 (8)	−0.0005 (7)	−0.0143 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.7401 (16)	C11—C12	1.378 (3)
N1—C7	1.3168 (18)	C11—H11	0.9400
N1—C4	1.3621 (18)	C12—C13	1.383 (3)
N2—C8	1.3216 (19)	C12—H12	0.9400
N2—C5	1.3602 (19)	C13—C14	1.384 (2)
C1—C6	1.359 (2)	C13—H13	0.9400
C1—C2	1.408 (2)	C14—H14	0.9400
C2—C3	1.366 (2)	C15—C16	1.194 (2)
C2—H2	0.9400	C16—C17	1.431 (2)
C3—C4	1.410 (2)	C17—C18	1.398 (2)
C3—H3	0.9400	C17—C22	1.400 (2)
C4—C5	1.417 (2)	C18—C19	1.373 (2)
C5—C6	1.408 (2)	C18—H18	0.9400
C6—H6	0.9400	C19—C20	1.384 (2)
C7—C8	1.445 (2)	C19—H19	0.9400
C7—C9	1.488 (2)	C20—C21	1.375 (2)
C8—C15	1.432 (2)	C20—H20	0.9400
C9—C10	1.389 (2)	C21—C22	1.378 (2)
C9—C14	1.397 (2)	C21—H21	0.9400
C10—C11	1.389 (2)	C22—H22	0.9400
C10—H10	0.9400

C7—N1—C4	118.09 (11)	C12—C11—C10	119.90 (17)
C8—N2—C5	117.11 (12)	C12—C11—H11	120.1
C6—C1—C2	122.68 (14)	C10—C11—H11	120.1
C6—C1—Cl1	119.67 (12)	C11—C12—C13	119.87 (16)
C2—C1—Cl1	117.65 (12)	C11—C12—H12	120.1
C3—C2—C1	119.21 (14)	C13—C12—H12	120.1
C3—C2—H2	120.4	C12—C13—C14	120.66 (17)
C1—C2—H2	120.4	C12—C13—H13	119.7
C2—C3—C4	120.20 (13)	C14—C13—H13	119.7
C2—C3—H3	119.9	C13—C14—C9	119.90 (16)
C4—C3—H3	119.9	C13—C14—H14	120.0
N1—C4—C3	119.84 (12)	C9—C14—H14	120.0
N1—C4—C5	120.75 (13)	C16—C15—C8	178.49 (18)
C3—C4—C5	119.39 (13)	C15—C16—C17	174.90 (17)
N2—C5—C6	119.21 (12)	C18—C17—C22	118.90 (14)
N2—C5—C4	121.04 (13)	C18—C17—C16	120.00 (13)
C6—C5—C4	119.75 (13)	C22—C17—C16	120.97 (14)
C1—C6—C5	118.58 (13)	C19—C18—C17	120.41 (14)
C1—C6—H6	120.7	C19—C18—H18	119.8
C5—C6—H6	120.7	C17—C18—H18	119.8
N1—C7—C8	120.60 (12)	C18—C19—C20	120.15 (15)
N1—C7—C9	116.64 (12)	C18—C19—H19	119.9
C8—C7—C9	122.65 (12)	C20—C19—H19	119.9
N2—C8—C15	116.82 (12)	C21—C20—C19	119.98 (14)
N2—C8—C7	122.04 (12)	C21—C20—H20	120.0
C15—C8—C7	121.08 (13)	C19—C20—H20	120.0
C10—C9—C14	118.97 (14)	C20—C21—C22	120.73 (14)
C10—C9—C7	118.40 (14)	C20—C21—H21	119.6
C14—C9—C7	122.62 (15)	C22—C21—H21	119.6
C9—C10—C11	120.69 (16)	C21—C22—C17	119.76 (15)
C9—C10—H10	119.7	C21—C22—H22	120.1
C11—C10—H10	119.7	C17—C22—H22	120.1

C6—C1—C2—C3	−2.8 (3)	N1—C7—C9—C10	44.3 (2)
Cl1—C1—C2—C3	176.92 (13)	C8—C7—C9—C10	−132.03 (16)
C1—C2—C3—C4	0.9 (3)	N1—C7—C9—C14	−134.37 (16)
C7—N1—C4—C3	−178.15 (14)	C8—C7—C9—C14	49.3 (2)
C7—N1—C4—C5	3.5 (2)	C14—C9—C10—C11	−1.0 (2)
C2—C3—C4—N1	−175.48 (15)	C7—C9—C10—C11	−179.69 (14)
C2—C3—C4—C5	2.9 (2)	C9—C10—C11—C12	0.9 (3)
C8—N2—C5—C6	−176.75 (14)	C10—C11—C12—C13	0.1 (3)
C8—N2—C5—C4	3.1 (2)	C11—C12—C13—C14	−1.1 (3)
N1—C4—C5—N2	−6.4 (2)	C12—C13—C14—C9	1.0 (3)
C3—C4—C5—N2	175.30 (14)	C10—C9—C14—C13	0.0 (2)
N1—C4—C5—C6	173.49 (14)	C7—C9—C14—C13	178.65 (14)
C3—C4—C5—C6	−4.8 (2)	N2—C8—C15—C16	−108 (6)
C2—C1—C6—C5	0.8 (3)	C7—C8—C15—C16	70 (6)
Cl1—C1—C6—C5	−178.91 (12)	C8—C15—C16—C17	−23 (7)
N2—C5—C6—C1	−177.12 (15)	C15—C16—C17—C18	−56.4 (18)
C4—C5—C6—C1	3.0 (2)	C15—C16—C17—C22	119.5 (18)
C4—N1—C7—C8	2.0 (2)	C22—C17—C18—C19	−2.4 (3)
C4—N1—C7—C9	−174.41 (13)	C16—C17—C18—C19	173.60 (16)
C5—N2—C8—C15	179.58 (14)	C17—C18—C19—C20	0.3 (3)
C5—N2—C8—C7	2.5 (2)	C18—C19—C20—C21	1.3 (3)
N1—C7—C8—N2	−5.3 (2)	C19—C20—C21—C22	−0.8 (3)
C9—C7—C8—N2	170.89 (15)	C20—C21—C22—C17	−1.3 (3)
N1—C7—C8—C15	177.74 (14)	C18—C17—C22—C21	2.9 (3)
C9—C7—C8—C15	−6.1 (2)	C16—C17—C22—C21	−173.08 (15)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg2ⁱ	0.94	3.00	3.845 (2)	151

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₃ClN₂
M_r	340.79
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	8.8652 (13), 9.8591 (8), 10.9740 (17)
α, β, γ (°)	73.032 (15), 81.036 (17), 64.374 (13)
V (Å³)	826.68 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.70 × 0.45 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.649, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	7504, 3714, 2855
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.128, 1.07
No. of reflections	3714
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2002).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg2ⁱ	0.94	3.00	3.845 (2)	151

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was funded by the Project of the Education Department of Guangxi Province (No. 201106LX593) and the Youth Foundation of Hechi University (No. 2011B-N004).

References

Ammermann, S., Daniliuc, C., Jones, P. G., Mont, W.-W. du & Johannes, H.-H. (2008). Acta Cryst. E64, o1205–o1206. Web of Science CSD CrossRef IUCr Journals Google Scholar
Daouda, B., Brelot, L., Doumbia, M. L., Essassi, E. M. & Ng, S. W. (2011). Acta Cryst. E67, o1235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, N. D., Abdullah, Z., Tajuddin, H. A., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2429. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hegedus, L. S., Greenberg, M. M., Wendling, J. J. & Bullock, J. P. (2003). J. Org. Chem. 68, 4179–4188. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Naraso, Nishida, J., Kumaki, D., Tokito, S. & Yamashita, Y. (2006). J. Am. Chem. Soc. 128, 9598–9599. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ramli, Y., Zouihri, H., Essassi, E. M. & Ng, S. W. (2012). Acta Cryst. E68, o241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2002). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rodrigo, G. A., Robinshon, A. E., Hedrera, M. E., Kogan, M., Sicardi, S. M. & Fernaandez, B. M. (2002). Trends Heterocycl. Chem. 8, 137–143. CAS Google Scholar
Sashidhara, K. V., Kumar, A., Bhatia, G., Khan, M. M., Khanna, A. K. & Saxena, J. K. (2009). Eur. J. Med. Chem. 44, 1813–1818. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkins, A. J., Nicol, G. W. & Shawa, L. J. (2009). Soil Biol. Biochem. 41, 580–585. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1741

doi:10.1107/S1600536812020776

Open

access