(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyrid-yl)ethyl-idene]indolin-2-one.

The title compound, C(23)H(16)N(2)O(3), 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, mol-ecules are inter-connected into a three-dimensional framework via inter-molecular C-H⋯O and C-H⋯N hydrogen bonds and weak π-π inter-actions [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. (2004 ▶). For related indoline structures, see: Fun et al. (2010 ▶); 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 = 368.38

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.04

5017 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030874/ci5150Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H16N2O3	Z = 2
Mr = 368.38	F(000) = 384
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0637P)2 + 0.2808P] where P = (Fo2 + 2Fc2)/3
5017 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .