2-[3-(2-Acetoxyphenyl)quinoxa­lin-2-yl]phenyl acetate

Shen, D.-F.; Lou, S.-J.; Xu, D.-Q.

doi:10.1107/S1600536813009161

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o764

https://doi.org/10.1107/S1600536813009161

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2-[3-(2-Acetoxyphenyl)quinoxalin-2-yl]phenyl acetate

Dan-Feng Shen,^a Shao-Jie Lou ^a and Dan-Qian Xu ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
^*Correspondence e-mail: chrc@zjut.edu.cn

(Received 25 March 2013; accepted 4 April 2013; online 20 April 2013)

The title compound, C₂₄H₁₈N₂O₄, crystallizes as a syn-conformer, with dihedral angles between the quinoxaline moiety and the acetoxy-substituted benzene rings of 53.46 (3)° and 54.78 (3)°. In the crystal, the molecules form chains along [100] via C—H⋯O interactions.

Related literature

For general background to quinoxaline derivatives, see: Brasche & Buchwald (2008 ); Do & Daugulis (2008 ); He et al. (2003 ); Kim et al. (2004 ); Lyons & Sanford (2010 ). For quinoxaline-directed C—H activation, see: Reddy et al. (2011 ). For a related structure, see: Rajnikant et al. (2006 ).

Experimental

Crystal data

C₂₄H₁₈N₂O₄
M_r = 398.40
Monoclinic, P 2₁ /c
a = 9.5723 (5) Å
b = 16.7309 (8) Å
c = 13.0555 (6) Å
β = 92.929 (2)°
V = 2088.15 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.48 × 0.46 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.959, T_max = 0.983
15632 measured reflections
3646 independent reflections
2553 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.117
S = 1.00
3646 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4ⁱ	0.93	2.43	3.329 (2)	164
Symmetry code: (i) x-1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009161/ld2099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009161/ld2099Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009161/ld2099Isup3.cml

checkCIF report

Comment top

Quinoxaline derivatives have received considerable interest from chemists because of their pharmacological properties such as antiviral, antibacterial, anti-inflammatory, and antiprotozoal activities, and as kinase inhibitors. C—H activation is a versatile approach for the direct functionalization of aromatic C—H bonds using transition metal catalysis. Palladium complexes are particularly attractive catalysts for such transformations. The molecular structure of the title compound is presented on Fig. 1. The plane of the quinoxaline moiety makes angles of 53.46 (3)°, 54.78 (3)° with the planes of phenyl rings. The torsion angle C9—C1—C8—C17 is 4.91 (3)°.

Related literature top

For general background to quinoxaline derivatives, see: Brasche & Buchwald (2008); Do & Daugulis (2008); He et al. (2003); Kim et al. (2004); Lyons & Sanford (2010). For quinoxaline-directed C—H activation, see: Reddy et al. (2011). For a related structure, see: Rajnikant et al. (2006).

Experimental top

A mixture of 2,3-diphenylquinoxaline (282 mg,1.0 mmol), phenyliodine diacetate (805 mg, 2.5 mmol), and Palladium acetate (34 mg, 0.15 mmol) in acetic acid-acetic anhydride (3.0 ml-3.0 ml) was stirred at room temperature for 10 min, then the resulting mixture was heated to 120 degrees for 4hr. After completion of reaction as indicated by TLC, the reaction mixture was filtered, diluted with water and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate salt, concentrated in vacuo, and purified by column chromatography on silica gel (eluent:petroleum ether-ethyl acetate) to afford pure product with a 90 percent yield. Suitable crystals were obtained by slow evaporation of an ethanol solution.

Structure description top

For general background to quinoxaline derivatives, see: Brasche & Buchwald (2008); Do & Daugulis (2008); He et al. (2003); Kim et al. (2004); Lyons & Sanford (2010). For quinoxaline-directed C—H activation, see: Reddy et al. (2011). For a related structure, see: Rajnikant et al. (2006).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecule of the title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.

2-[3-(2-Acetoxyphenyl)quinoxalin-2-yl]phenyl acetate top

Crystal data top

C₂₄H₁₈N₂O₄	F(000) = 832
M_r = 398.40	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11299 reflections
a = 9.5723 (5) Å	θ = 3.1–27.4°
b = 16.7309 (8) Å	µ = 0.09 mm⁻¹
c = 13.0555 (6) Å	T = 296 K
β = 92.929 (2)°	Platelet, yellow
V = 2088.15 (18) Å³	0.48 × 0.46 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	3646 independent reflections
Radiation source: rotating anode	2553 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 10.00 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
T_min = 0.959, T_max = 0.983	l = −15→15
15632 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.045P)² + 0.7545P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
3646 reflections	Δρ_max = 0.17 e Å⁻³
274 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (2)

Crystal data top

C₂₄H₁₈N₂O₄	V = 2088.15 (18) Å³
M_r = 398.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5723 (5) Å	µ = 0.09 mm⁻¹
b = 16.7309 (8) Å	T = 296 K
c = 13.0555 (6) Å	0.48 × 0.46 × 0.20 mm
β = 92.929 (2)°

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	3646 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2553 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.983	R_int = 0.043
15632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
3646 reflections	Δρ_min = −0.20 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
C1	0.57616 (19)	0.12138 (11)	0.27152 (13)	0.0401 (4)
C2	0.7311 (2)	0.02174 (11)	0.31884 (15)	0.0467 (5)
C3	0.7625 (3)	−0.04950 (13)	0.37296 (19)	0.0678 (6)
H3	0.6940	−0.0747	0.4093	0.081*
C4	0.8934 (3)	−0.08127 (15)	0.3718 (2)	0.0778 (7)
H4	0.9141	−0.1280	0.4080	0.093*
C5	0.9964 (3)	−0.04432 (15)	0.3169 (2)	0.0783 (7)
H5	1.0850	−0.0671	0.3166	0.094*
C6	0.9699 (2)	0.02435 (14)	0.2639 (2)	0.0704 (7)
H6	1.0394	0.0480	0.2270	0.085*
C7	0.8360 (2)	0.05939 (12)	0.26533 (15)	0.0494 (5)
C8	0.68513 (19)	0.16210 (11)	0.22108 (14)	0.0429 (5)
C9	0.43173 (19)	0.15473 (11)	0.27655 (14)	0.0438 (5)
C10	0.3759 (2)	0.16739 (13)	0.37183 (17)	0.0586 (6)
H10	0.4290	0.1545	0.4312	0.070*
C11	0.2436 (3)	0.19857 (15)	0.3797 (2)	0.0714 (7)
H11	0.2083	0.2068	0.4439	0.086*
C12	0.1641 (2)	0.21744 (15)	0.2926 (2)	0.0731 (7)
H12	0.0751	0.2389	0.2980	0.088*
C13	0.2152 (2)	0.20474 (14)	0.19734 (19)	0.0628 (6)
H13	0.1610	0.2171	0.1383	0.075*
C14	0.3478 (2)	0.17335 (12)	0.19050 (15)	0.0473 (5)
C15	0.3570 (3)	0.09580 (15)	0.04113 (19)	0.0727 (7)
C16	0.4121 (3)	0.09362 (19)	−0.0632 (2)	0.0940 (9)
H16A	0.3871	0.0438	−0.0956	0.141*
H16B	0.5121	0.0987	−0.0581	0.141*
H16C	0.3727	0.1369	−0.1033	0.141*
C17	0.66704 (19)	0.24376 (11)	0.17661 (15)	0.0432 (5)
C18	0.6188 (2)	0.30646 (12)	0.23494 (17)	0.0537 (5)
H18	0.5930	0.2967	0.3015	0.064*
C19	0.6084 (2)	0.38308 (13)	0.19573 (19)	0.0622 (6)
H19	0.5755	0.4244	0.2357	0.075*
C20	0.6466 (2)	0.39806 (14)	0.09761 (19)	0.0650 (6)
H20	0.6390	0.4495	0.0710	0.078*
C21	0.6961 (2)	0.33717 (13)	0.03828 (17)	0.0577 (6)
H21	0.7231	0.3475	−0.0279	0.069*
C22	0.70544 (19)	0.26088 (11)	0.07788 (15)	0.0448 (5)
C23	0.8838 (2)	0.19247 (13)	−0.00467 (16)	0.0554 (5)
C24	0.9139 (3)	0.11638 (17)	−0.0569 (2)	0.0940 (9)
H24A	1.0092	0.1164	−0.0765	0.141*
H24B	0.8524	0.1108	−0.1169	0.141*
H24C	0.8997	0.0726	−0.0111	0.141*
N1	0.59936 (17)	0.05326 (9)	0.32027 (12)	0.0467 (4)
N2	0.81105 (17)	0.13064 (10)	0.21658 (13)	0.0513 (4)
O1	0.40006 (15)	0.16132 (9)	0.09276 (10)	0.0569 (4)
O2	0.2849 (3)	0.04774 (14)	0.0780 (2)	0.1502 (12)
O3	0.74576 (14)	0.19711 (8)	0.01622 (10)	0.0536 (4)
O4	0.96565 (16)	0.24378 (10)	0.01729 (13)	0.0718 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0399 (11)	0.0407 (10)	0.0397 (9)	−0.0011 (8)	0.0016 (8)	−0.0007 (8)
C2	0.0485 (12)	0.0394 (11)	0.0519 (11)	0.0026 (9)	−0.0016 (9)	0.0003 (8)
C3	0.0670 (16)	0.0531 (13)	0.0834 (16)	0.0067 (11)	0.0054 (12)	0.0188 (12)
C4	0.0777 (19)	0.0577 (15)	0.0972 (19)	0.0184 (13)	−0.0026 (15)	0.0172 (13)
C5	0.0593 (16)	0.0675 (16)	0.108 (2)	0.0249 (13)	−0.0009 (14)	0.0111 (14)
C6	0.0494 (14)	0.0646 (15)	0.0979 (18)	0.0147 (11)	0.0098 (12)	0.0115 (13)
C7	0.0457 (12)	0.0445 (11)	0.0580 (12)	0.0051 (9)	0.0015 (9)	0.0023 (9)
C8	0.0384 (11)	0.0427 (11)	0.0477 (11)	0.0002 (8)	0.0036 (8)	0.0007 (8)
C9	0.0381 (11)	0.0445 (11)	0.0492 (11)	−0.0024 (8)	0.0060 (9)	0.0029 (8)
C10	0.0454 (13)	0.0746 (15)	0.0564 (12)	0.0038 (11)	0.0086 (10)	0.0019 (10)
C11	0.0522 (15)	0.0910 (18)	0.0725 (16)	0.0059 (13)	0.0183 (12)	−0.0046 (13)
C12	0.0405 (13)	0.0788 (17)	0.101 (2)	0.0113 (11)	0.0109 (13)	−0.0055 (14)
C13	0.0432 (13)	0.0661 (15)	0.0781 (16)	0.0040 (10)	−0.0068 (11)	0.0070 (11)
C14	0.0409 (12)	0.0490 (12)	0.0520 (11)	−0.0037 (9)	0.0017 (9)	0.0033 (9)
C15	0.0844 (18)	0.0636 (15)	0.0710 (16)	−0.0143 (14)	0.0131 (14)	−0.0085 (12)
C16	0.115 (2)	0.103 (2)	0.0653 (16)	−0.0082 (18)	0.0090 (16)	−0.0149 (15)
C17	0.0332 (10)	0.0432 (11)	0.0529 (11)	−0.0009 (8)	0.0005 (8)	0.0054 (8)
C18	0.0493 (13)	0.0485 (12)	0.0640 (13)	0.0034 (9)	0.0088 (10)	0.0036 (10)
C19	0.0546 (14)	0.0455 (13)	0.0865 (17)	0.0056 (10)	0.0044 (12)	0.0014 (11)
C20	0.0543 (14)	0.0490 (13)	0.0905 (17)	0.0007 (11)	−0.0080 (12)	0.0190 (12)
C21	0.0513 (13)	0.0609 (14)	0.0600 (13)	−0.0052 (10)	−0.0063 (10)	0.0185 (11)
C22	0.0328 (10)	0.0477 (11)	0.0531 (11)	−0.0055 (8)	−0.0048 (8)	0.0040 (9)
C23	0.0490 (13)	0.0624 (14)	0.0552 (12)	−0.0057 (11)	0.0080 (10)	0.0018 (10)
C24	0.0787 (19)	0.088 (2)	0.118 (2)	−0.0099 (15)	0.0290 (17)	−0.0343 (17)
N1	0.0458 (10)	0.0428 (9)	0.0517 (9)	−0.0007 (7)	0.0033 (7)	0.0048 (7)
N2	0.0399 (10)	0.0489 (10)	0.0656 (11)	0.0035 (7)	0.0075 (8)	0.0065 (8)
O1	0.0542 (9)	0.0661 (10)	0.0501 (8)	−0.0107 (7)	−0.0014 (7)	0.0030 (7)
O2	0.218 (3)	0.0990 (16)	0.142 (2)	−0.0865 (18)	0.092 (2)	−0.0508 (14)
O3	0.0461 (8)	0.0589 (9)	0.0562 (8)	−0.0123 (6)	0.0052 (6)	−0.0055 (6)
O4	0.0485 (10)	0.0730 (11)	0.0944 (12)	−0.0164 (8)	0.0085 (8)	−0.0079 (9)

Geometric parameters (Å, º) top

C1—N1	1.319 (2)	C13—H13	0.9300
C1—C8	1.434 (2)	C14—O1	1.409 (2)
C1—C9	1.495 (3)	C15—O2	1.178 (3)
C2—N1	1.368 (2)	C15—O1	1.341 (3)
C2—C7	1.401 (3)	C15—C16	1.486 (3)
C2—C3	1.410 (3)	C16—H16A	0.9600
C3—C4	1.362 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.393 (4)	C17—C22	1.388 (3)
C4—H4	0.9300	C17—C18	1.389 (3)
C5—C6	1.359 (3)	C18—C19	1.382 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.410 (3)	C19—C20	1.373 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—N2	1.367 (2)	C20—C21	1.379 (3)
C8—N2	1.319 (2)	C20—H20	0.9300
C8—C17	1.491 (3)	C21—C22	1.378 (3)
C9—C14	1.383 (3)	C21—H21	0.9300
C9—C10	1.395 (3)	C22—O3	1.403 (2)
C10—C11	1.378 (3)	C23—O4	1.188 (2)
C10—H10	0.9300	C23—O3	1.365 (2)
C11—C12	1.372 (4)	C23—C24	1.479 (3)
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.376 (3)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.381 (3)

N1—C1—C8	121.58 (17)	C9—C14—O1	119.04 (17)
N1—C1—C9	115.76 (16)	O2—C15—O1	121.6 (2)
C8—C1—C9	122.60 (16)	O2—C15—C16	126.9 (3)
N1—C2—C7	121.18 (17)	O1—C15—C16	111.5 (2)
N1—C2—C3	119.48 (18)	C15—C16—H16A	109.5
C7—C2—C3	119.34 (19)	C15—C16—H16B	109.5
C4—C3—C2	119.8 (2)	H16A—C16—H16B	109.5
C4—C3—H3	120.1	C15—C16—H16C	109.5
C2—C3—H3	120.1	H16A—C16—H16C	109.5
C3—C4—C5	120.6 (2)	H16B—C16—H16C	109.5
C3—C4—H4	119.7	C22—C17—C18	117.67 (18)
C5—C4—H4	119.7	C22—C17—C8	121.31 (17)
C6—C5—C4	121.2 (2)	C18—C17—C8	120.91 (17)
C6—C5—H5	119.4	C19—C18—C17	121.1 (2)
C4—C5—H5	119.4	C19—C18—H18	119.4
C5—C6—C7	119.4 (2)	C17—C18—H18	119.4
C5—C6—H6	120.3	C20—C19—C18	119.8 (2)
C7—C6—H6	120.3	C20—C19—H19	120.1
N2—C7—C2	120.79 (17)	C18—C19—H19	120.1
N2—C7—C6	119.56 (19)	C19—C20—C21	120.3 (2)
C2—C7—C6	119.63 (19)	C19—C20—H20	119.8
N2—C8—C1	121.24 (17)	C21—C20—H20	119.8
N2—C8—C17	115.87 (16)	C22—C21—C20	119.4 (2)
C1—C8—C17	122.78 (16)	C22—C21—H21	120.3
C14—C9—C10	117.21 (18)	C20—C21—H21	120.3
C14—C9—C1	123.25 (17)	C21—C22—C17	121.62 (19)
C10—C9—C1	119.53 (17)	C21—C22—O3	120.24 (18)
C11—C10—C9	121.3 (2)	C17—C22—O3	118.01 (16)
C11—C10—H10	119.4	O4—C23—O3	123.0 (2)
C9—C10—H10	119.4	O4—C23—C24	126.2 (2)
C12—C11—C10	119.9 (2)	O3—C23—C24	110.8 (2)
C12—C11—H11	120.0	C23—C24—H24A	109.5
C10—C11—H11	120.0	C23—C24—H24B	109.5
C11—C12—C13	120.3 (2)	H24A—C24—H24B	109.5
C11—C12—H12	119.8	C23—C24—H24C	109.5
C13—C12—H12	119.8	H24A—C24—H24C	109.5
C12—C13—C14	119.2 (2)	H24B—C24—H24C	109.5
C12—C13—H13	120.4	C1—N1—C2	117.34 (16)
C14—C13—H13	120.4	C8—N2—C7	117.73 (16)
C13—C14—C9	122.07 (19)	C15—O1—C14	117.26 (16)
C13—C14—O1	118.89 (18)	C23—O3—C22	117.10 (15)

N1—C2—C3—C4	179.9 (2)	C1—C8—C17—C22	−131.55 (19)
C7—C2—C3—C4	−0.7 (3)	N2—C8—C17—C18	−124.0 (2)
C2—C3—C4—C5	−0.5 (4)	C1—C8—C17—C18	52.3 (3)
C3—C4—C5—C6	0.5 (4)	C22—C17—C18—C19	0.5 (3)
C4—C5—C6—C7	0.7 (4)	C8—C17—C18—C19	176.78 (19)
N1—C2—C7—N2	2.8 (3)	C17—C18—C19—C20	−0.2 (3)
C3—C2—C7—N2	−176.6 (2)	C18—C19—C20—C21	−0.4 (3)
N1—C2—C7—C6	−178.78 (19)	C19—C20—C21—C22	0.8 (3)
C3—C2—C7—C6	1.8 (3)	C20—C21—C22—C17	−0.5 (3)
C5—C6—C7—N2	176.6 (2)	C20—C21—C22—O3	175.29 (18)
C5—C6—C7—C2	−1.9 (4)	C18—C17—C22—C21	−0.1 (3)
N1—C1—C8—N2	3.9 (3)	C8—C17—C22—C21	−176.41 (18)
C9—C1—C8—N2	−178.99 (17)	C18—C17—C22—O3	−176.01 (17)
N1—C1—C8—C17	−172.21 (17)	C8—C17—C22—O3	7.7 (3)
C9—C1—C8—C17	4.9 (3)	C8—C1—N1—C2	−1.5 (3)
N1—C1—C9—C14	−124.4 (2)	C9—C1—N1—C2	−178.85 (16)
C8—C1—C9—C14	58.4 (3)	C7—C2—N1—C1	−1.7 (3)
N1—C1—C9—C10	54.9 (2)	C3—C2—N1—C1	177.72 (19)
C8—C1—C9—C10	−122.4 (2)	C1—C8—N2—C7	−2.7 (3)
C14—C9—C10—C11	−1.2 (3)	C17—C8—N2—C7	173.69 (17)
C1—C9—C10—C11	179.5 (2)	C2—C7—N2—C8	−0.5 (3)
C9—C10—C11—C12	0.3 (4)	C6—C7—N2—C8	−178.93 (19)
C10—C11—C12—C13	0.6 (4)	O2—C15—O1—C14	−4.3 (4)
C11—C12—C13—C14	−0.5 (4)	C16—C15—O1—C14	176.0 (2)
C12—C13—C14—C9	−0.5 (3)	C13—C14—O1—C15	−79.8 (3)
C12—C13—C14—O1	−179.3 (2)	C9—C14—O1—C15	101.3 (2)
C10—C9—C14—C13	1.3 (3)	O4—C23—O3—C22	−8.4 (3)
C1—C9—C14—C13	−179.44 (19)	C24—C23—O3—C22	171.6 (2)
C10—C9—C14—O1	−179.88 (17)	C21—C22—O3—C23	74.4 (2)
C1—C9—C14—O1	−0.6 (3)	C17—C22—O3—C23	−109.70 (19)
N2—C8—C17—C22	52.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4ⁱ	0.93	2.43	3.329 (2)	164

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₂O₄
M_r	398.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.5723 (5), 16.7309 (8), 13.0555 (6)
β (°)	92.929 (2)
V (Å³)	2088.15 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.46 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID/ZJUG
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.959, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15632, 3646, 2553
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.00
No. of reflections	3646
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4ⁱ	0.93	2.43	3.329 (2)	163.5

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank Professor Jian-Ming Gu of Zhejiang University for his help.

References

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