(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyrid­yl)ethyl­idene]indolin-2-one

Fun, H.-K.; Goh, J.H.; Yu, H.; Zhang, Y.

doi:10.1107/S1600536810030874

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2232-o2233

https://doi.org/10.1107/S1600536810030874

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(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyridyl)ethylidene]indolin-2-one

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Haitao Yu ^b and Yan Zhang ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 2 August 2010; accepted 2 August 2010; online 11 August 2010)

The title compound, C₂₃H₁₆N₂O₃, exists in a Z configuration with respect to the acyclic C=C bond. The pyridine and phenyl rings are oriented at dihedral angles of 72.97 (4) and 45.05 (4)°, respectively, with respect to the almost planar indoline ring system [maximum deviation 0.080 (1) Å]. The pyridine and phenyl rings are oriented almost perpendicular to each other [dihedral angle 88.93 (5)°]. In the crystal, molecules are interconnected into a three-dimensional framework via intermolecular C—H⋯O and C—H⋯N hydrogen bonds and weak π–π interactions [centroid–centroid distance = 3.681 (1) Å].

Related literature

For general background and applications of indoline compounds, see: Aanandhi et al. (2008 ); Lawrence et al. (2008 ); Muthukumar et al. (2008 ); Wang et al. (2005 ); Xue et al. (2000 ); Yu et al. (2010 ); Zhang & Panek (2009 ); Zhang et al. (2004a ,b ). For related indoline structures, see: Fun et al. (2010a ,b ); Usman et al. (2001 ,2002 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₁₆N₂O₃
M_r = 368.38
Triclinic, $[P \overline 1]$
a = 7.9259 (19) Å
b = 9.086 (2) Å
c = 12.431 (3) Å
α = 84.804 (7)°
β = 87.064 (7)°
γ = 76.843 (6)°
V = 867.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.23 × 0.19 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.978, T_max = 0.985
19600 measured reflections
5017 independent reflections
4237 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.04
5017 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.44 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
C12—H12A⋯O3ⁱ	0.93	2.37	3.2518 (16)	158
C14—H14A⋯O2ⁱⁱ	0.93	2.53	3.2381 (16)	133
C20—H20A⋯N2ⁱⁱⁱ	0.93	2.58	3.3238 (17)	137
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030874/ci5150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030874/ci5150Isup2.hkl

checkCIF report

Comment top

Indole derivatives have a variety of biological activities and are synthetic precursors for many naturally occuring alkaloids (Aanandhi et al., 2008; Muthukumar et al., 2008; Lawrence et al., 2008). The C3 carbonyl group is the common reactive group in isatin (1H-indole-2,3-dione) for further derivation in either thermal reactions or photoreactions (Zhang et al., 2004b; 2009). Photoreactions of N-acetylisatin and alkenes or alkynes have provided a facile way to build various heterocyclic frameworks containing indole moieties (Wang et al., 2005; Zhang et al., 2004a; Xue et al., 2000). Azaaryl substituted acetylenes have been used to react with carbonyl groups which may lead to formation of various heterocyclic polycycles (Yu et al., 2010). In view of the importance of the title compound, (I), as a typical quinone methide product in photoreaction between carbonyl and acetylenes, this paper reports its crystal structure.

The title molecule exists in a cis configuration with respect to the acyclic C8═C9 bond [C8═C9 = 1.3510 (14) Å]. The indoline ring system (C1-C8/N1) is essentially planar, with a maximum deviation of 0.080 (1) Å at atom C7. The phenyl ring (C16-C21) and pyridine ring (C11-C15/N2) are almost perpendicular to each other, as indicated by the interplanar angle of 88.93 (5)° between them. These two rings form dihedral angles of 72.97 (4) and 45.05 (4)° with the indoline ring system, respectively. The bond lengths and angles are consistent to those observed in closely related indole structures (Fun et al., 2010a,b; Usman et al., 2001,2002).

In the crystal packing, intermolecular C12—H12A···O3, C14—H14A···O2 and C20—H20A···N2 hydrogen bonds (Table 1) interconnect adjacent molecules into a three-dimensional framework (Fig. 2). Weak intermolecular π-π interactions involving the pyrrolidine (C1/C6-C8/N1, centroid Cg1) and phenyl (C1-C6, centroid Cg2) rings [Cg1···Cg2^* = 3.6812 (11) Å; symmetry code: (*) 2-x, 2-y, -z] further stabilize the crystal packing.

Related literature top

For general background and applications of indoline compounds, see: Aanandhi et al. (2008); Lawrence et al. (2008); Muthukumar et al. (2008); Wang et al. (2005); Xue et al. (2000); Yu et al. (2010); Zhang & Panek (2009); Zhang et al. (2004a,b). For related indoline structures, see: Fun et al. (2010a,b); Usman et al. (2001,2002). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained in the reaction between N-acetylisatin and 3-pyridinyl phenyl acetylene under photo-irradiation with light of wavelength > 400 nm. The compound was purified by flash column chromatography with ethyl acetate-petroleum ether (1:5) as eluents. X-ray quality single crystals of (I) were obtained by slow evaporation of a acetone-petroleum ether (1:2) solution (m.p. 568–571 K).

Structure description top

For general background and applications of indoline compounds, see: Aanandhi et al. (2008); Lawrence et al. (2008); Muthukumar et al. (2008); Wang et al. (2005); Xue et al. (2000); Yu et al. (2010); Zhang & Panek (2009); Zhang et al. (2004a,b). For related indoline structures, see: Fun et al. (2010a,b); Usman et al. (2001,2002). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 50 % probability level.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis, showing a three-dimensional framework. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyridyl)ethylidene]indolin-2-one top

Crystal data top

C₂₃H₁₆N₂O₃	Z = 2
M_r = 368.38	F(000) = 384
Triclinic, P1	D_x = 1.410 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9259 (19) Å	Cell parameters from 7658 reflections
b = 9.086 (2) Å	θ = 2.3–32.1°
c = 12.431 (3) Å	µ = 0.10 mm⁻¹
α = 84.804 (7)°	T = 100 K
β = 87.064 (7)°	Block, yellow
γ = 76.843 (6)°	0.23 × 0.19 × 0.16 mm
V = 867.7 (4) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5017 independent reflections
Radiation source: fine-focus sealed tube	4237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 30.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.978, T_max = 0.985	k = −12→12
19600 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0637P)² + 0.2808P] where P = (F_o² + 2F_c²)/3
5017 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₁₆N₂O₃	γ = 76.843 (6)°
M_r = 368.38	V = 867.7 (4) Å³
Triclinic, P1	Z = 2
a = 7.9259 (19) Å	Mo Kα radiation
b = 9.086 (2) Å	µ = 0.10 mm⁻¹
c = 12.431 (3) Å	T = 100 K
α = 84.804 (7)°	0.23 × 0.19 × 0.16 mm
β = 87.064 (7)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5017 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4237 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.985	R_int = 0.028
19600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	Δρ_max = 0.44 e Å⁻³
5017 reflections	Δρ_min = −0.20 e Å⁻³
254 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.74656 (11)	0.64928 (9)	0.08150 (6)	0.01988 (17)
O2	0.94194 (10)	0.51863 (9)	0.29214 (7)	0.01842 (17)
O3	0.61891 (12)	0.98853 (10)	−0.16758 (7)	0.02319 (19)
N1	0.72823 (12)	0.89175 (10)	−0.00538 (7)	0.01472 (18)
N2	0.48355 (13)	0.38455 (11)	0.38814 (8)	0.0208 (2)
C1	0.80969 (13)	1.00838 (12)	0.13505 (8)	0.01429 (19)
C2	0.86200 (14)	1.12405 (12)	0.18121 (9)	0.0175 (2)
H2A	0.8958	1.1110	0.2526	0.021*
C3	0.86325 (15)	1.25906 (13)	0.11949 (10)	0.0200 (2)
H3A	0.8961	1.3375	0.1501	0.024*
C4	0.81564 (16)	1.27772 (13)	0.01211 (10)	0.0220 (2)
H4A	0.8160	1.3692	−0.0279	0.026*
C5	0.76744 (15)	1.16211 (13)	−0.03661 (9)	0.0199 (2)
H5A	0.7379	1.1742	−0.1088	0.024*
C6	0.76495 (13)	1.02835 (12)	0.02614 (8)	0.0149 (2)
C7	0.75826 (13)	0.77964 (12)	0.08245 (8)	0.01466 (19)
C8	0.79925 (13)	0.85485 (11)	0.17647 (8)	0.01383 (19)
C9	0.80773 (13)	0.78123 (11)	0.27615 (8)	0.01317 (19)
C10	0.80593 (13)	0.61403 (11)	0.29125 (8)	0.01361 (19)
C11	0.63598 (13)	0.57473 (11)	0.31789 (8)	0.01344 (19)
C12	0.47958 (14)	0.67902 (12)	0.29924 (9)	0.0165 (2)
H12A	0.4784	0.7776	0.2711	0.020*
C13	0.32642 (14)	0.63324 (13)	0.32333 (9)	0.0187 (2)
H13A	0.2201	0.6996	0.3104	0.022*
C14	0.33486 (14)	0.48613 (13)	0.36719 (9)	0.0192 (2)
H14A	0.2312	0.4559	0.3831	0.023*
C15	0.63067 (14)	0.42976 (12)	0.36275 (9)	0.0170 (2)
H15A	0.7352	0.3606	0.3757	0.020*
C16	0.80906 (13)	0.84819 (11)	0.38002 (8)	0.01300 (19)
C17	0.90394 (13)	0.76491 (12)	0.46632 (8)	0.0148 (2)
H17A	0.9728	0.6691	0.4568	0.018*
C18	0.89565 (14)	0.82461 (12)	0.56573 (9)	0.0164 (2)
H18A	0.9591	0.7688	0.6226	0.020*
C19	0.79292 (14)	0.96743 (12)	0.58082 (9)	0.0173 (2)
H19A	0.7894	1.0079	0.6472	0.021*
C20	0.69532 (14)	1.04977 (12)	0.49644 (9)	0.0169 (2)
H20A	0.6253	1.1448	0.5068	0.020*
C21	0.70218 (13)	0.99052 (12)	0.39705 (9)	0.0150 (2)
H21A	0.6355	1.0455	0.3412	0.018*
C22	0.66296 (14)	0.87655 (13)	−0.10556 (9)	0.0168 (2)
C23	0.65025 (17)	0.72265 (14)	−0.13229 (10)	0.0238 (2)
H23D	0.6085	0.7288	−0.2041	0.036*
H23A	0.5715	0.6849	−0.0817	0.036*
H23B	0.7626	0.6552	−0.1283	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0294 (4)	0.0142 (4)	0.0177 (4)	−0.0079 (3)	−0.0024 (3)	−0.0016 (3)
O2	0.0157 (3)	0.0153 (4)	0.0234 (4)	−0.0011 (3)	−0.0024 (3)	−0.0019 (3)
O3	0.0304 (4)	0.0212 (4)	0.0168 (4)	−0.0038 (3)	−0.0049 (3)	0.0021 (3)
N1	0.0193 (4)	0.0125 (4)	0.0125 (4)	−0.0037 (3)	−0.0008 (3)	−0.0007 (3)
N2	0.0205 (5)	0.0161 (4)	0.0260 (5)	−0.0057 (4)	−0.0015 (4)	0.0014 (4)
C1	0.0149 (4)	0.0134 (4)	0.0147 (5)	−0.0037 (4)	0.0014 (3)	−0.0010 (3)
C2	0.0196 (5)	0.0168 (5)	0.0175 (5)	−0.0067 (4)	0.0016 (4)	−0.0029 (4)
C3	0.0230 (5)	0.0148 (5)	0.0239 (6)	−0.0076 (4)	0.0035 (4)	−0.0038 (4)
C4	0.0262 (6)	0.0145 (5)	0.0250 (6)	−0.0062 (4)	0.0030 (4)	0.0016 (4)
C5	0.0248 (5)	0.0167 (5)	0.0176 (5)	−0.0048 (4)	0.0002 (4)	0.0017 (4)
C6	0.0166 (4)	0.0132 (4)	0.0147 (5)	−0.0035 (4)	0.0015 (3)	−0.0017 (4)
C7	0.0167 (4)	0.0141 (4)	0.0130 (4)	−0.0033 (4)	−0.0004 (3)	−0.0008 (4)
C8	0.0150 (4)	0.0129 (4)	0.0141 (5)	−0.0038 (3)	−0.0006 (3)	−0.0017 (3)
C9	0.0121 (4)	0.0126 (4)	0.0151 (5)	−0.0032 (3)	−0.0010 (3)	−0.0015 (3)
C10	0.0157 (4)	0.0128 (4)	0.0122 (4)	−0.0028 (4)	−0.0022 (3)	−0.0006 (3)
C11	0.0149 (4)	0.0126 (4)	0.0131 (4)	−0.0035 (4)	−0.0015 (3)	−0.0009 (3)
C12	0.0168 (5)	0.0135 (4)	0.0182 (5)	−0.0022 (4)	−0.0006 (4)	0.0017 (4)
C13	0.0142 (4)	0.0191 (5)	0.0213 (5)	−0.0015 (4)	−0.0010 (4)	0.0013 (4)
C14	0.0177 (5)	0.0207 (5)	0.0204 (5)	−0.0074 (4)	−0.0001 (4)	−0.0010 (4)
C15	0.0159 (5)	0.0129 (4)	0.0213 (5)	−0.0020 (4)	−0.0024 (4)	0.0007 (4)
C16	0.0136 (4)	0.0130 (4)	0.0130 (4)	−0.0048 (3)	−0.0002 (3)	−0.0004 (3)
C17	0.0154 (4)	0.0135 (4)	0.0154 (5)	−0.0031 (4)	−0.0007 (4)	−0.0003 (4)
C18	0.0181 (5)	0.0175 (5)	0.0138 (5)	−0.0047 (4)	−0.0028 (4)	0.0009 (4)
C19	0.0213 (5)	0.0176 (5)	0.0139 (5)	−0.0059 (4)	0.0013 (4)	−0.0028 (4)
C20	0.0194 (5)	0.0138 (4)	0.0169 (5)	−0.0026 (4)	0.0025 (4)	−0.0024 (4)
C21	0.0159 (4)	0.0139 (4)	0.0145 (5)	−0.0030 (4)	−0.0004 (3)	0.0006 (4)
C22	0.0169 (5)	0.0194 (5)	0.0136 (5)	−0.0023 (4)	0.0002 (4)	−0.0030 (4)
C23	0.0328 (6)	0.0205 (5)	0.0189 (5)	−0.0051 (5)	−0.0066 (4)	−0.0047 (4)

Geometric parameters (Å, º) top

O1—C7	1.2100 (13)	C11—C15	1.3919 (15)
O2—C10	1.2196 (13)	C11—C12	1.3940 (14)
O3—C22	1.2146 (14)	C12—C13	1.3807 (15)
N1—C22	1.4027 (14)	C12—H12A	0.93
N1—C7	1.4146 (13)	C13—C14	1.3854 (16)
N1—C6	1.4293 (14)	C13—H13A	0.93
N2—C15	1.3360 (15)	C14—H14A	0.93
N2—C14	1.3421 (15)	C15—H15A	0.93
C1—C2	1.3920 (15)	C16—C17	1.4020 (14)
C1—C6	1.4025 (15)	C16—C21	1.4026 (14)
C1—C8	1.4614 (14)	C17—C18	1.3866 (15)
C2—C3	1.3884 (16)	C17—H17A	0.93
C2—H2A	0.93	C18—C19	1.3890 (15)
C3—C4	1.3909 (17)	C18—H18A	0.93
C3—H3A	0.93	C19—C20	1.3914 (15)
C4—C5	1.3920 (17)	C19—H19A	0.93
C4—H4A	0.93	C20—C21	1.3855 (15)
C5—C6	1.3868 (15)	C20—H20A	0.93
C5—H5A	0.93	C21—H21A	0.93
C7—C8	1.4911 (14)	C22—C23	1.4925 (16)
C8—C9	1.3510 (14)	C23—H23D	0.96
C9—C16	1.4779 (14)	C23—H23A	0.96
C9—C10	1.5169 (15)	C23—H23B	0.96
C10—C11	1.4844 (15)

C22—N1—C7	126.23 (9)	C13—C12—H12A	120.6
C22—N1—C6	124.62 (9)	C11—C12—H12A	120.6
C7—N1—C6	109.05 (8)	C12—C13—C14	118.45 (10)
C15—N2—C14	116.88 (10)	C12—C13—H13A	120.8
C2—C1—C6	119.44 (10)	C14—C13—H13A	120.8
C2—C1—C8	132.38 (10)	N2—C14—C13	123.95 (10)
C6—C1—C8	108.08 (9)	N2—C14—H14A	118.0
C3—C2—C1	119.30 (10)	C13—C14—H14A	118.0
C3—C2—H2A	120.3	N2—C15—C11	123.54 (10)
C1—C2—H2A	120.3	N2—C15—H15A	118.2
C2—C3—C4	120.41 (10)	C11—C15—H15A	118.2
C2—C3—H3A	119.8	C17—C16—C21	118.84 (10)
C4—C3—H3A	119.8	C17—C16—C9	120.64 (9)
C3—C4—C5	121.29 (10)	C21—C16—C9	120.24 (9)
C3—C4—H4A	119.4	C18—C17—C16	120.34 (10)
C5—C4—H4A	119.4	C18—C17—H17A	119.8
C6—C5—C4	117.78 (11)	C16—C17—H17A	119.8
C6—C5—H5A	121.1	C17—C18—C19	120.29 (10)
C4—C5—H5A	121.1	C17—C18—H18A	119.9
C5—C6—C1	121.74 (10)	C19—C18—H18A	119.9
C5—C6—N1	128.68 (10)	C18—C19—C20	119.87 (10)
C1—C6—N1	109.51 (9)	C18—C19—H19A	120.1
O1—C7—N1	126.06 (10)	C20—C19—H19A	120.1
O1—C7—C8	127.05 (10)	C21—C20—C19	120.17 (10)
N1—C7—C8	106.84 (9)	C21—C20—H20A	119.9
C9—C8—C1	133.76 (10)	C19—C20—H20A	119.9
C9—C8—C7	119.91 (10)	C20—C21—C16	120.45 (10)
C1—C8—C7	106.16 (9)	C20—C21—H21A	119.8
C8—C9—C16	126.82 (10)	C16—C21—H21A	119.8
C8—C9—C10	120.64 (9)	O3—C22—N1	119.12 (10)
C16—C9—C10	112.44 (9)	O3—C22—C23	122.22 (10)
O2—C10—C11	122.38 (10)	N1—C22—C23	118.65 (10)
O2—C10—C9	120.09 (9)	C22—C23—H23D	109.5
C11—C10—C9	117.10 (9)	C22—C23—H23A	109.5
C15—C11—C12	118.37 (10)	H23D—C23—H23A	109.5
C15—C11—C10	119.66 (9)	C22—C23—H23B	109.5
C12—C11—C10	121.97 (9)	H23D—C23—H23B	109.5
C13—C12—C11	118.78 (10)	H23A—C23—H23B	109.5

C6—C1—C2—C3	2.16 (16)	C16—C9—C10—O2	−91.54 (12)
C8—C1—C2—C3	177.86 (11)	C8—C9—C10—C11	−95.54 (12)
C1—C2—C3—C4	−1.10 (17)	C16—C9—C10—C11	81.14 (11)
C2—C3—C4—C5	−0.66 (18)	O2—C10—C11—C15	10.99 (16)
C3—C4—C5—C6	1.30 (17)	C9—C10—C11—C15	−161.52 (10)
C4—C5—C6—C1	−0.20 (17)	O2—C10—C11—C12	−168.92 (10)
C4—C5—C6—N1	−176.92 (10)	C9—C10—C11—C12	18.58 (15)
C2—C1—C6—C5	−1.54 (16)	C15—C11—C12—C13	−1.65 (16)
C8—C1—C6—C5	−178.19 (10)	C10—C11—C12—C13	178.26 (10)
C2—C1—C6—N1	175.75 (9)	C11—C12—C13—C14	1.31 (16)
C8—C1—C6—N1	−0.91 (12)	C15—N2—C14—C13	−1.21 (18)
C22—N1—C6—C5	−9.52 (17)	C12—C13—C14—N2	0.14 (18)
C7—N1—C6—C5	173.99 (11)	C14—N2—C15—C11	0.83 (17)
C22—N1—C6—C1	173.44 (9)	C12—C11—C15—N2	0.58 (17)
C7—N1—C6—C1	−3.05 (12)	C10—C11—C15—N2	−179.33 (10)
C22—N1—C7—O1	6.86 (17)	C8—C9—C16—C17	−146.10 (11)
C6—N1—C7—O1	−176.72 (10)	C10—C9—C16—C17	37.46 (13)
C22—N1—C7—C8	−170.80 (9)	C8—C9—C16—C21	40.03 (15)
C6—N1—C7—C8	5.61 (11)	C10—C9—C16—C21	−136.40 (10)
C2—C1—C8—C9	13.1 (2)	C21—C16—C17—C18	−1.83 (15)
C6—C1—C8—C9	−170.79 (11)	C9—C16—C17—C18	−175.78 (9)
C2—C1—C8—C7	−171.80 (11)	C16—C17—C18—C19	0.13 (16)
C6—C1—C8—C7	4.26 (11)	C17—C18—C19—C20	1.24 (16)
O1—C7—C8—C9	−7.79 (17)	C18—C19—C20—C21	−0.87 (17)
N1—C7—C8—C9	169.84 (9)	C19—C20—C21—C16	−0.86 (16)
O1—C7—C8—C1	176.33 (11)	C17—C16—C21—C20	2.19 (15)
N1—C7—C8—C1	−6.04 (11)	C9—C16—C21—C20	176.17 (10)
C1—C8—C9—C16	8.63 (19)	C7—N1—C22—O3	168.91 (10)
C7—C8—C9—C16	−165.88 (9)	C6—N1—C22—O3	−6.97 (16)
C1—C8—C9—C10	−175.20 (10)	C7—N1—C22—C23	−11.15 (16)
C7—C8—C9—C10	10.28 (15)	C6—N1—C22—C23	172.96 (10)
C8—C9—C10—O2	91.78 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3ⁱ	0.93	2.37	3.2518 (16)	158
C14—H14A···O2ⁱⁱ	0.93	2.53	3.2381 (16)	133
C20—H20A···N2ⁱⁱⁱ	0.93	2.58	3.3238 (17)	137

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆N₂O₃
M_r	368.38
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9259 (19), 9.086 (2), 12.431 (3)
α, β, γ (°)	84.804 (7), 87.064 (7), 76.843 (6)
V (Å³)	867.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.978, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	19600, 5017, 4237
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.04
No. of reflections	5017
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3ⁱ	0.93	2.37	3.2518 (16)	158
C14—H14A···O2ⁱⁱ	0.93	2.53	3.2381 (16)	133
C20—H20A···N2ⁱⁱⁱ	0.93	2.58	3.3238 (17)	137

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the Ministry of Science and Technology of China on the Austria-China Cooperation project (2007DFA41590) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

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