Hydrogen-bonding patterns in 3-alkyl-3-hydroxy­indolin-2-ones

The mol­ecules of racemic 3-benzoyl­methyl-3-hydroxy­indolin-2-one, C₁₆H₁₃NO₃, (I), are linked by a combination of N-H...O and O-H...O hydrogen bonds into a chain of centrosymmetric edge-fused R₂²(10) and R₄⁴(12) rings. Five monosubstituted analogues of (I), namely racemic 3-hydr­oxy-3-[(4-methyl­benzoyl)methyl]indolin-2-one, C₁₇H₁₅NO₃, (II), racemic 3-[(4-fluoro­benzoyl)methyl]-3-hydroxy­indolin-2-one, C₁₆H₁₂FNO₃, (III), racemic 3-[(4-chloro­benzoyl)methyl]-3-hy­droxy­indolin-2-one, C₁₆H₁₂ClNO₃, (IV), racemic 3-[(4-bromo­benzoyl)methyl]-3-hydroxy­indolin-2-one, C₁₆H₁₂BrNO₃, (V), and racemic 3-hydr­oxy-3-[(4-nitro­benzoyl)­methyl]­indolin-2-one, C₁₆H₁₂N₂O₅, (VI), are isomorphous in space group P. In each of compounds (II)-(VI), a combination of N-H...O and O-H...O hydrogen bonds generates a chain of centrosymmetric edge-fused R₂²(8) and R₂²(10) rings, and these chains are linked into sheets by an aromatic [pi]-[pi] stacking inter­action. No two of the structures of (II)-(VI) exhibit the same combination of weak hydrogen bonds of C-H...O and C-H...[pi](arene) types. The mol­ecules of racemic 3-hydr­oxy-3-(2-thienylcarbonyl­methyl)indolin-2-one, C₁₄H₁₁NO₃S, (VII), form hydrogen-bonded chains very similar to those in (II)-(VI), but here the sheet formation depends upon a weak [pi]-[pi] stacking inter­action between thienyl rings. Comparisons are drawn between the crystal structures of compounds (I)-(VII) and those of some recently reported analogues having no aromatic group in the side chain.

S1. Comment

We report here the structures of seven racemic 3-hydroxy-3-(2-aryl-2-oxoethyl)indolin-2-ones, compounds (I)–(VII) (Fig. 1), which we compare with the structures of a number of analogues, (VIII)–(XII), in the recent literature (Luppi et al., 2005, 2006; Xing et al., 2007; Chen et al., 2009). Chalcones are versatile bis-electrophilic reagents widely employed in the synthesis of fused heterocyclic systems, and compounds (I)–(VII) have been prepared as precursors for the formation of chalcones by acid-catalysed dehydration reactions.

Compounds (I)–(VII) were all prepared by reactions of isatin with methyl ketones using basic catalysis (see scheme), as were the analogues (VIII)–(XII). The compounds all contain a stereogenic centre, at atom C3 in (I)–(VII) (Fig. 1), and if an achiral base is employed as the catalytic agent, as here, the products are obtained as racemic mixtures. However, if an enantiomerically pure form of a chiral base is used, then the products are found with a significant excess of one enantiomer over the other, as in the syntheses of (IX) (Luppi et al., 2007), (XI) (Luppi et al., 2006) and (XII) (Xing et al., 2007).

As expected from the method of synthesis, (I)–(VII) all crystallize as racemic mixtures and all crystallize in centrosymmetric space groups. However, while compound (I), which contains an unsubstituted phenyl ring in the side chain (Fig. 1a) crystallizes in the space group P2₁/c, compounds (II)–(VI), which all contain a single substituent at the 4-position of this ring (Figs. 1b-1f), are all isomorphous in the space group P1. Compound (VII), which contains a 2-thienyl unit rather than an aryl ring in the side chain (Fig. 1g), also crystallizes in space group P1 and the unit-cell repeat distances a, b and c are similar to those in compounds (II)–(VI). The unit-cell angles have approximately complementary values to those in (II)–(VI) and the atom coordinates in (VII) are approximately related to those of the corresponding atoms in (II)–(VI) by the transformation (1 - x, y, 1 - z). However, comparison of the reduced-cell parameters shows that, despite these similarities, compound (VII) is not isomorphous with the series (II)–(VI).

In the crystal structure of (I), molecules related by translation are linked by an N—H···O hydrogen bond (Table 1) to form a C(5) (Bernstein et al., 1995) chain running parallel to the [010] direction. Antiparallel pairs of such chains are linked by an O—H···O hydrogen bond to generate a chain of centrosymmetric edge-fused rings, in which R₂²(10) rings centred at (1/2, n + 1/2, 1/2), where n represents an integer, alternate with R₄⁴(12) rings centred at (1/2, n, 1/2), where n again represents an integer (Fig. 2). Two chains of this type pass through each unit cell but there are no direction-specific interactions of structural significance between adjacent chains.

Although compounds (II)-(VI) are isomorphous, they are not strictly isostructural (Acosta et al., 2009), as the pattern of the weaker hydrogen bonds of C—H···O and C—H..π(arene) types differs between the members of the series, such that no two of (II)–(VI) show an identical array of such interactions. Indeed, no interactions of these types occur in the structure of (II), while some of them are present in the structures of each of (III)–(VI). It is thus convenient to describe first the actions of the N—H···O and O—H···O hydrogen bonds and the aromatic π–π stacking interactions in compound (II), which are in fact the same in each of (II)–(VI), and then briefly to note the actions of the weaker hydrogen bonds in each of (III)–(VI).

In compound (II), symmetry-related pairs of O—H···O hydrogen bonds (Table 1) link the molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) to form an R₂²(10) motif, while similar pairs of N—H···O hydrogen bonds link the molecules at (x, y, z) and (-x, 1 - y, 1 - z) to form an R₂²(8) motif. Propagation by inversion of these two motifs then generates a chain of edge-fused rings running parallel to the [100] direction, in which the R₂²(10) rings are centred at (n + 1/2, 1/2, 1/2) and the R₂²(8) rings are centred at (n, 1/2, 1/2), where in both cases n represents an integer (Fig. 3). This chain of rings differs from that formed by (I) in two important respects. Firstly, both hydrogen bonds in (II) utilize the amidic atom O2 as the acceptor, whereas in (I) the N—H···O hydrogen bond utilizes the hydroxyl atom O3 as the acceptor. Secondly, the chain in (II) is propagated solely by inversion, while a combination of translation and inversion propagates the chain in (I). However, one feature in common between these two chains is that in neither type does the ketonic atom O32 in the side chain participate in the N—H···O or O—H···O hydrogen bonds. The hydrogen-bonded chains in (II) are linked by a single aromatic π–π stacking interaction involving the C321–C326 phenyl rings in the molecules at (x, y, z) and (2 - x, 1 - y, 2 - z) (Table 2). These two molecules form parts of the hydrogen-bonded chains along (x, 1/2, 1/2) and (x, 1/2, 3/2), respectively, so that propagation of this π–π stacking interaction links the hydrogen-bonded chains into a sheet parallel to (010).

The formation of hydrogen-bonded [100] chains containing alternating R₂²(8) and R₂²(10) rings and linked by a π–π stacking interaction into sheets parallel to (010) is common to each of (II)–(VI) (Tables 1 and 2), and the sheet formation provides another point of difference between the crystal structures of (II)–(VI) on the one hand and that of (I) on the other. However, the structures of each of (III)–(VI) exhibit further weak interactions, different in each case, and thus different from the structure of (II). In each of (IV), (V) and (VI), although not in (II) or (III), there are C—H···O hydrogen bonds which reinforce, albeit weakly, the chains along [100], and in each of (III) and (IV), but not in (II), (V) or (VI), there is a C—H···π(arene) hydrogen bond which reinforces the linkage of the [100] chains into sheets. Although the structures of both (V) and (VI) contain C—H···O hydrogen bonds, the number of these interactions differs in the two structures (Table 1). In addition, it may be noted that the ketonic atom O32 is involved only in C—H···O interactions in compounds (IV), (V) and (VI), rather than in N—H···O or O—H···O hydrogen bonds. Similarly, the only interaction involving a nitro group O atom in (VI) is of C—H···O type.

In compound (VII), a chain of edge-fused R₂²(8) and R₂²(10) rings along [100] is formed (Fig. 4), similar to those in (II)–(VI), but the orientation of the hydrogen-bonded structure relative to the unit cell is different in (VII) from those in (II)–(VI) (Figs. 3 and 4). As with (IV)–(VI), the structure of (VII) contains two C—H···O contacts within the hydrogen-bonded chains; these have rather long H···O distances and only one of them involves the hydroxyl atom O3. However, the chains along [100] are again linked into sheets, this time rather weakly, by a π–π stacking interaction involving the thienyl rings of the molecules at (x, y, z) and (1 - x, 1 - y, -z). These rings are strictly parallel with an interplanar spacing of 3.368 (2) Å; the ring-centroid separation is 3.746 (2) Å, corresponding to a ring-centroid offset of 1.640 (2) Å. These two molecules are components of the hydrogen-bonded chains along (x, 1/2, 1/2) and (x, 1/2, -1/2), respectively, so that this π–π stacking interaction links the hydrogen-bonded chains into a sheet parallel to (010), similar to those in (II)–(VI).

It is of interest to compare the structures of (I)–(VII) with those of some recently reported analogues, (VIII)–(XII), several of which have been reported only briefly, usually on a simple proof-of-constitution or proof-of-configuration basis. Compounds (VIII)–(XII) differ from (I)–(VII) in several respects. Firstly, they have no aryl or heteroaryl group in the side chain, thus reducing the scope for the formation of C—H···O and C—H···π(arene) hydrogen bonds and of aromatic π–π stacking interactions. Secondly, compounds (IX), (XI) and (XII) crystallize in Sohncke space groups so that only a single enantiomer is present in a given crystal (provided that twinning is shown to be absent). Finally, compound (X) is a hemihydrate, while solvent molecules are not found in any other member of this series.

Compound (VIII) [Cambridge Structural Database (CSD; Allen, 2002) refcode MUBMAY; Chen et al., 2009] crystallizes as a racemic mixture in the space group P2₁/c, and a combination of N—H···O and O—H···O hydrogen bonds generates a chain of alternating R₂²(10) and R₄⁴(12) rings propagated by translation and inversion along the [010] direction, entirely analogous to the chain in (I).

Compounds (IX) (CSD refcode TAWDUR; Luppi et al., 2007) and (X) (CSD refcode TAWFAZ; Luppi et al., 2007) were crystallized from the same solution following reaction of 5-bromoisatin with acetone catalysed by an enantiomerically pure D-prolyl dipeptide. Compound (XI) is the pure R enantiomer crystallizing in the space group P2₁, while (X) is a hemihydrate of the racemic mixture, which crystallizes in space group C2/c. For (IX), the original report (Luppi et al., 2007) indicated the formation of a hydrogen-bonded chain of rings, although without providing any details, but the structure of (X) was not mentioned at all. Re-examination of the structure of (IX) using the deposited atomic coordinates shows that molecules related by a 2₁ screw axis along (1/2, y, 0) are linked by N—H···O and O—H···O hydrogen bonds to form a chain of edge-fused R³₃(11) rings (Fig. 5), with no direction-specific interactions between the chains.

Analysis of the structure of (X) using the deposited atomic coordinates shows that the hydrogen bonding links the molecular components into a three-dimensional framework structure, the formation of which is readily analysed in terms of the actions of the three hydrogen bonds in turn. Enantiomeric pairs of the organic component are linked by pairs of symmetry-related O—H···O hydrogen bonds, forming centrosymmetric R₂²(10) dimers, analogous to those observed in (II)–(VIII). These dimers are linked by the N—H···O hydrogen bond to form a sheet parallel to (100), containing both R₂²(10) and R⁶₆(22) rings and lying in the domain (0 < x < 1/2) (Fig. 6). The water molecule lies on a twofold rotation axis along (1/2, y, 1/4) and forms pairs of O—H···O hydrogen bonds which link adjacent (100) sheets, so linking all of the molecules into a single three-dimensional structure.

The structure of the (R)-enantiomer of (XI) (CSD refcode TEQVUH; Luppi et al., 2006) was reported as a proof of constitution and configuration, as shown by the value, -0.006 (8), of the Flack x parameter (Flack, 1983), but no description or discussion of the crystal structure was given. This single enantiomer crystallizes in the space group P2₁2₁2₁ and examination of the crystal structure using the deposited atomic coordinates shows the formation of a chain of edge-fused R₂²(9) rings built from molecules related by the 2₁ screw axis along (x, 3/4, 1) and linked by N—H···O and O—H···O hydrogen bonds (Fig. 7).

Compound (XII) (CSD refcode YIFZIX; Xing et al., 2007) also crystallizes in space group P2₁2₁2₁ and the Flack x parameter of 0.03 (8) indicates that only a single enantiomer is present in the crystal selected for data collection. However, the identity of this enantiomer is nowhere specified in the original report, although the deposited coordinates correspond to the (S)-enantiomer, consistent with the reported use of an L-prolyl amide as the catalytic base. The crystal structure was described as consisting of a chain of centrosymmetric R₂²(9) rings, but this description must be incorrect on two grounds, firstly because centrosymmetric motifs cannot contain an odd number of atoms, and secondly because centrosymmetric motifs cannot be formed in the noncentrosymmetric space group P2₁2₁2₁. The packing diagram provided by the authors does not show a chain. In fact, re-examination of this structure shows that it contains a chain of R₂²(9) rings entirely analogous to the chain in compound (XI), but built from molecules related by the 2₁ screw axis along (x, 1/4, 1/2) (Fig. 8).

Compounds (I)–(XIII) discussed here exhibit several distinct patterns formed by conventional strong hydrogen bonds of N—H···O and O—H···O types. Thus, (I) and (VIII) form entirely similar hydrogen-bonded chains, despite the differences between the steric requirements of the terminal groups in their side chains, phenyl in (I) and isopropyl in (VIII). A second pattern of chain formation is found in the isomorphous compounds (II)–(VI), as well as in (VII). A third type of chain formation is shared by the enantiomerically pure compounds (XI) and (XII). By contrast, the single enantiomer of compound (IX) forms a chain type unlike those in any of racemic compounds (I)–(VIII), or in the enantiomerically pure compounds (XI) and (XII), while in the racemic hemihydrate (X), where the organic component is the same as in (IX), the N—H···O and O—H···O hydrogen bonds between the organic molecules form a sheet structure unlike any other compound in this series.

For compounds (I)–(VII), the O···O distances in the O—H···O hydrogen bonds are all very similar (Table 1), as are the N···O distances in the N—H···O hydrogen bonds in (II)–(VII). However, wide variations occur across this series in the D···A distances of the weaker interactions, suggesting that many of these may be adventitious contacts rather than significant structure builders.

S2. Experimental

Samples of compounds (I)–(VII) were prepared following a reported general procedure using piperidine as the catalytic base (Kusanur et al., 2004). Yellow–brown crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of solutions in a mixture of ethanol and dimethylformamide (1:1, v/v).

Analysis for (I), 3-benzoylmethyl-3-hydroxyindolin-2-one, yield 40%, m.p. 423–425 K (decomposition) (literature value 442–445 K; Lindwall & Maclennan, 1932); MS (EI) m/z (% abundance) 249 (6), 222 (100), 119 (41), 105 (86).

Analysis for (II), 3-hydroxy-3-[(4-methylbenzoyl)methyl]indolin-2-one, yield 43%, m.p. 458 K (decomposition) (literature value 458–460 K; Lindwall & Maclennan, 1932); MS (EI) m/z (% abundance) 281 [M⁺] (1), 263 (3), 236 (34), 119 (100).

Analysis for (III), 3-[(4-fluorobenzoyl)methyl]-3-hydroxyindolin-2-one, yield 46%, m.p. 489–491 K (decomposition); MS (EI) m/z (% abundance) 285 [M⁺] (2), 267 (3), 240 (40), 123 (100), 119 (41).

Analysis for (IV), 3-[(4-chlorobenzoyl)methyl]-3-hydroxyindolin-2-one, yield 60%, m.p. 465–467 K (decomposition) (literature value 470–472 K; Popp & Donigan, 1979); MS (EI) m/z (% abundance) 303 [M + 2] (0.6), 301 [M⁺] (1.4), 285 (1.2), 283 (2.5), 258 (15), 256 (40), 141 (32), 139 (100), 119 (57).

Analysis for (V), 3-[(4-bromobenzoyl)methyl]-3-hydroxyindolin-2-one, yield 55%, m.p. 462–464 K (decomposition) (literature value 448–453 K; Lindwall & Maclennan, 1932); MS (EI) m/z (% abundance) 347 [M + 2] (1.1), 345 [M⁺] (1.0), 230 (1), 228 (1), 302 (31), 300 (32), 185 (100), 183 (98), 119 (95).

Analysis for (VI), 3-hydroxy-3-[(4-nitrobenzoyl)methyl]indolin-2-one, yield 45%, m.p. 449–451 K (decomposition) (literature value 458–460 K; Popp & Donigan, 1979); MS (EI) m/z (% abundance) 312 [M⁺] (1.0), 294 (5.6), 267 (6.0), 150 (100), 119 (54).

Analysis for (VII), 3-hydroxy-3-(2-thienylcarbonylmethyl)indolin-2-one, yield 39%, m.p. 476–478 K (decomposition); MS (EI) m/z (% abundance) 273 [M⁺] (1), 255 (4), 228 (34), 119 (51).

S3. Refinement

All H atoms were located in difference maps. H atoms bonded to C or N atoms were then treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (aromatic and thienyl), 0.98 (CH₃) or 0.99 Å (CH₂), and N—H = 0.88 Å, and with U_iso(H) = kU_eq(C,N), where k = 1.5 for the methyl group in compound (II), which was permitted to rotate but not to tilt, and 1.2 for all other H atoms bonded to C or N atoms. H atoms bonded to O atoms were permitted to ride at the positions deduced from difference maps, with U_iso(H) = 1.5U_eq(O), giving O—H distances in the range 0.82–0.87 Å (Table 1). Compound (IV) was treated as a non-merohedral twin. A modified .hkl file was prepared using the TwinRotMat option in PLATON (Spek, 2009) and used with the HKLF5 option in SHELXL (Sheldrick, 2008), giving twin fractions of 0.269 (2) and 0.731 (2), respectively.

Computing details

For all compounds, data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structures of compounds (I)–(VII), showing the atom-labelling schemes. (a) Compound (I), (b) compound (II), (c) compound (III), (d) compound (IV), (e) compound (V), (f) compound (VI) and (g) compound (VII). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of alternating R2^2(10) and R4^4(12) rings along [100]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted
	Fig. 3. A stereoview of part of the crystal structure of (II), showing the formation of a hydrogen-bonded chain of alternating R2^2(8) and R2^2(10) rings along [100]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 4. A stereoview of part of the crystal structure of (VII), showing the formation of a hydrogen-bonded chain of alternating R2^2(8) and R2^2(10) rings along [100]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted. Note the orientations of the unit cell and the chain relative to those in Fig. 3.
	Fig. 5. A stereoview of part of the crystal structure of (IX) (CSD refcode TAWDUR; Luppi et al., 2007), showing the formation of a hydrogen-bonded chain of edge-fused R^33(11) rings along [010]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 6. A stereoview of part of the crystal structure of (X) (CSD refcode TAWFAZ; Luppi et al., 2007), showing the formation by the organic components of a hydrogen-bonded sheet parallel to (100) and containing R2^2(10) and R^66(22) rings. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 7. A stereoview of part of the crystal structure of (XI) (CSD refcode TEQVUH; Luppi et al., 2006), showing the formation of a hydrogen-bonded chain of edge-fused R2^2(9) rings along [100]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 8. A stereoview of part of the crystal structure of (XII) (CSD refcode YIFZIX; Xing et al., 2007), showing the formation of a hydrogen-bonded chain of edge-fused R2^2(9) rings along [100]. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.

(I) 3-benzoylmethyl-3-hydroxyindolin-2-one

Crystal data

C16H13NO3	F(000) = 560
Mr = 267.27	Dx = 1.430 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2427 reflections
a = 13.876 (3) Å	θ = 2.6–26.0°
b = 5.7725 (8) Å	µ = 0.10 mm^−1
c = 16.280 (3) Å	T = 120 K
β = 107.799 (16)°	Block, yellow-brown
V = 1241.6 (4) Å^3	0.26 × 0.23 × 0.18 mm
Z = 4

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2427 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −7→7
Tmin = 0.975, Tmax = 0.982	l = −20→20
15921 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 2.5504P] where P = (Fo^2 + 2Fc^2)/3
2427 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.40791 (17)	0.3278 (4)	0.58214 (15)	0.0146 (5)
H1	0.4318	0.1855	0.5867	0.018*
C2	0.3847 (2)	0.4529 (5)	0.50900 (18)	0.0143 (6)
C3	0.3529 (2)	0.6970 (5)	0.52967 (18)	0.0142 (6)
C3a	0.3531 (2)	0.6688 (5)	0.62093 (18)	0.0132 (6)
C4	0.3283 (2)	0.8225 (5)	0.67536 (18)	0.0152 (6)
H4	0.3017	0.9708	0.6552	0.018*
C5	0.3425 (2)	0.7578 (5)	0.76054 (18)	0.0168 (6)
H5	0.3272	0.8637	0.7995	0.020*
C6	0.3789 (2)	0.5404 (5)	0.78854 (18)	0.0155 (6)
H6	0.3870	0.4977	0.8466	0.019*
C7	0.4040 (2)	0.3815 (5)	0.73413 (18)	0.0155 (6)
H7	0.4298	0.2325	0.7540	0.019*
C7a	0.3897 (2)	0.4499 (5)	0.65032 (18)	0.0138 (6)
O2	0.39414 (14)	0.3922 (3)	0.44025 (12)	0.0160 (4)
O3	0.42819 (14)	0.8585 (3)	0.52291 (12)	0.0144 (4)
H3	0.4850	0.8025	0.5421	0.022*
C31	0.2547 (2)	0.7797 (5)	0.46707 (18)	0.0146 (6)
H31A	0.2358	0.9289	0.4879	0.017*
H31B	0.2651	0.8082	0.4104	0.017*
C32	0.1690 (2)	0.6124 (5)	0.45514 (17)	0.0155 (6)
O32	0.18472 (15)	0.4188 (4)	0.48581 (14)	0.0217 (5)
C321	0.0658 (2)	0.6845 (5)	0.40225 (18)	0.0164 (6)
C322	0.0473 (2)	0.8981 (5)	0.36121 (19)	0.0207 (7)
H322	0.1003	1.0083	0.3699	0.025*
C323	−0.0485 (2)	0.9498 (6)	0.3078 (2)	0.0235 (7)
H323	−0.0610	1.0949	0.2790	0.028*
C324	−0.1259 (2)	0.7926 (6)	0.2961 (2)	0.0233 (7)
H324	−0.1915	0.8288	0.2588	0.028*
C325	−0.1088 (2)	0.5835 (6)	0.3382 (2)	0.0236 (7)
H325	−0.1628	0.4768	0.3310	0.028*
C326	−0.0134 (2)	0.5280 (5)	0.39092 (19)	0.0206 (7)
H326	−0.0017	0.3826	0.4196	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0178 (12)	0.0102 (11)	0.0158 (12)	0.0025 (10)	0.0051 (9)	0.0000 (10)
C2	0.0097 (13)	0.0150 (14)	0.0169 (14)	−0.0024 (11)	0.0021 (11)	−0.0006 (12)
C3	0.0151 (13)	0.0114 (14)	0.0164 (14)	−0.0024 (11)	0.0054 (11)	−0.0002 (11)
C3a	0.0114 (13)	0.0138 (14)	0.0145 (13)	−0.0022 (11)	0.0038 (11)	−0.0005 (11)
C4	0.0135 (13)	0.0134 (14)	0.0189 (14)	−0.0002 (11)	0.0052 (11)	−0.0002 (12)
C5	0.0156 (14)	0.0179 (15)	0.0174 (14)	−0.0014 (12)	0.0058 (11)	−0.0040 (12)
C6	0.0140 (13)	0.0200 (15)	0.0124 (13)	−0.0032 (12)	0.0039 (11)	0.0002 (12)
C7	0.0145 (13)	0.0139 (14)	0.0170 (14)	−0.0016 (11)	0.0033 (11)	0.0003 (12)
C7a	0.0101 (13)	0.0153 (14)	0.0168 (14)	−0.0011 (11)	0.0051 (11)	−0.0017 (12)
O2	0.0176 (10)	0.0165 (10)	0.0148 (10)	−0.0003 (8)	0.0065 (8)	−0.0031 (8)
O3	0.0107 (9)	0.0139 (10)	0.0191 (10)	0.0003 (8)	0.0053 (8)	0.0004 (8)
C31	0.0121 (13)	0.0163 (15)	0.0148 (13)	−0.0005 (11)	0.0035 (11)	−0.0002 (12)
C32	0.0185 (14)	0.0157 (15)	0.0127 (13)	−0.0012 (12)	0.0055 (11)	−0.0016 (12)
O32	0.0202 (11)	0.0154 (11)	0.0268 (12)	0.0001 (9)	0.0033 (9)	0.0045 (9)
C321	0.0168 (14)	0.0199 (15)	0.0125 (13)	0.0009 (12)	0.0043 (11)	−0.0029 (12)
C322	0.0193 (15)	0.0192 (16)	0.0223 (15)	0.0000 (13)	0.0044 (12)	−0.0005 (13)
C323	0.0248 (16)	0.0215 (16)	0.0216 (15)	0.0032 (13)	0.0034 (13)	0.0020 (13)
C324	0.0155 (15)	0.0314 (18)	0.0209 (16)	0.0049 (13)	0.0023 (12)	−0.0027 (14)
C325	0.0159 (14)	0.0298 (18)	0.0255 (16)	−0.0049 (13)	0.0068 (13)	−0.0038 (14)
C326	0.0209 (15)	0.0197 (16)	0.0210 (15)	−0.0008 (13)	0.0063 (12)	0.0004 (13)

Geometric parameters (Å, º)

N1—C2	1.345 (4)	O3—H3	0.8201
N1—C7a	1.402 (4)	C31—C32	1.497 (4)
N1—H1	0.8800	C31—H31A	0.9900
C2—O2	1.217 (3)	C31—H31B	0.9900
C2—C3	1.544 (4)	C32—O32	1.216 (3)
C3—O3	1.429 (3)	C32—C321	1.487 (4)
C3—C3a	1.494 (4)	C321—C322	1.388 (4)
C3—C31	1.508 (4)	C321—C326	1.391 (4)
C3a—C4	1.371 (4)	C322—C323	1.380 (4)
C3a—C7a	1.391 (4)	C322—H322	0.9500
C4—C5	1.391 (4)	C323—C324	1.374 (4)
C4—H4	0.9500	C323—H323	0.9500
C5—C6	1.377 (4)	C324—C325	1.373 (5)
C5—H5	0.9500	C324—H324	0.9500
C6—C7	1.391 (4)	C325—C326	1.377 (4)
C6—H6	0.9500	C325—H325	0.9500
C7—C7a	1.375 (4)	C326—H326	0.9500
C7—H7	0.9500
C2—N1—C7a	112.3 (2)	C3a—C7a—N1	108.6 (2)
C2—N1—H1	123.9	C3—O3—H3	110.7
C7a—N1—H1	123.9	C32—C31—C3	113.7 (2)
O2—C2—N1	126.5 (3)	C32—C31—H31A	108.8
O2—C2—C3	125.5 (3)	C3—C31—H31A	108.8
N1—C2—C3	107.7 (2)	C32—C31—H31B	108.8
O3—C3—C3a	111.6 (2)	C3—C31—H31B	108.8
O3—C3—C31	105.8 (2)	H31A—C31—H31B	107.7
C3a—C3—C31	115.7 (2)	O32—C32—C321	121.0 (3)
O3—C3—C2	108.3 (2)	O32—C32—C31	120.2 (3)
C3a—C3—C2	101.7 (2)	C321—C32—C31	118.7 (2)
C31—C3—C2	113.6 (2)	C322—C321—C326	119.4 (3)
C4—C3a—C7a	120.2 (3)	C322—C321—C32	122.1 (3)
C4—C3a—C3	130.4 (3)	C326—C321—C32	118.5 (3)
C7a—C3a—C3	109.3 (2)	C323—C322—C321	119.8 (3)
C3a—C4—C5	118.9 (3)	C323—C322—H322	120.1
C3a—C4—H4	120.5	C321—C322—H322	120.1
C5—C4—H4	120.5	C324—C323—C322	120.4 (3)
C6—C5—C4	120.1 (3)	C324—C323—H323	119.8
C6—C5—H5	120.0	C322—C323—H323	119.8
C4—C5—H5	120.0	C325—C324—C323	120.2 (3)
C5—C6—C7	121.8 (3)	C325—C324—H324	119.9
C5—C6—H6	119.1	C323—C324—H324	119.9
C7—C6—H6	119.1	C324—C325—C326	120.2 (3)
C7a—C7—C6	117.0 (3)	C324—C325—H325	119.9
C7a—C7—H7	121.5	C326—C325—H325	119.9
C6—C7—H7	121.5	C325—C326—C321	120.1 (3)
C7—C7a—C3a	121.9 (3)	C325—C326—H326	119.9
C7—C7a—N1	129.4 (3)	C321—C326—H326	119.9
C7a—N1—C2—O2	178.9 (3)	C3—C3a—C7a—C7	176.0 (2)
C7a—N1—C2—C3	4.0 (3)	C4—C3a—C7a—N1	179.3 (2)
O2—C2—C3—O3	−62.9 (3)	C3—C3a—C7a—N1	−3.4 (3)
N1—C2—C3—O3	112.1 (2)	C2—N1—C7a—C7	−179.9 (3)
O2—C2—C3—C3a	179.4 (3)	C2—N1—C7a—C3a	−0.5 (3)
N1—C2—C3—C3a	−5.6 (3)	O3—C3—C31—C32	171.3 (2)
O2—C2—C3—C31	54.4 (4)	C3a—C3—C31—C32	−64.5 (3)
N1—C2—C3—C31	−130.6 (2)	C2—C3—C31—C32	52.6 (3)
O3—C3—C3a—C4	67.0 (4)	C3—C31—C32—O32	−8.9 (4)
C31—C3—C3a—C4	−54.1 (4)	C3—C31—C32—C321	173.6 (2)
C2—C3—C3a—C4	−177.7 (3)	O32—C32—C321—C322	−175.1 (3)
O3—C3—C3a—C7a	−109.9 (3)	C31—C32—C321—C322	2.4 (4)
C31—C3—C3a—C7a	129.1 (3)	O32—C32—C321—C326	2.1 (4)
C2—C3—C3a—C7a	5.4 (3)	C31—C32—C321—C326	179.6 (3)
C7a—C3a—C4—C5	1.5 (4)	C326—C321—C322—C323	−1.9 (4)
C3—C3a—C4—C5	−175.1 (3)	C32—C321—C322—C323	175.3 (3)
C3a—C4—C5—C6	−1.5 (4)	C321—C322—C323—C324	1.0 (5)
C4—C5—C6—C7	1.2 (4)	C322—C323—C324—C325	0.7 (5)
C5—C6—C7—C7a	−0.8 (4)	C323—C324—C325—C326	−1.5 (5)
C6—C7—C7a—C3a	0.8 (4)	C324—C325—C326—C321	0.5 (5)
C6—C7—C7a—N1	−179.8 (3)	C322—C321—C326—C325	1.1 (4)
C4—C3a—C7a—C7	−1.2 (4)	C32—C321—C326—C325	−176.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.88	2.15	2.918 (3)	146
O3—H3···O2^ii	0.82	1.97	2.762 (3)	163

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

(II) 3-hydroxy-3-[(4-methylbenzoyl)methyl]indolin-2-one

Crystal data

C17H15NO3	Z = 2
Mr = 281.30	F(000) = 296
Triclinic, P1	Dx = 1.385 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.873 (2) Å	Cell parameters from 2520 reflections
b = 7.6700 (17) Å	θ = 2.7–25.5°
c = 13.394 (5) Å	µ = 0.10 mm^−1
α = 99.48 (2)°	T = 120 K
β = 101.68 (3)°	Plate, yellow-brown
γ = 96.33 (2)°	0.34 × 0.21 × 0.09 mm
V = 674.4 (4) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2520 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1783 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
Detector resolution: 9.091 pixels mm^-1	θmax = 25.5°, θmin = 2.7°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.968, Tmax = 0.992	l = −16→16
15497 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.3503P] where P = (Fo^2 + 2Fc^2)/3
2520 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0627 (3)	0.3203 (3)	0.57141 (17)	0.0215 (5)
H1	−0.0521	0.3582	0.5504	0.026*
C2	0.2392 (4)	0.4009 (3)	0.5669 (2)	0.0199 (6)
C3	0.4019 (4)	0.2903 (3)	0.6046 (2)	0.0195 (6)
C3a	0.2815 (4)	0.1467 (3)	0.6389 (2)	0.0199 (6)
C4	0.3367 (4)	0.0028 (3)	0.6808 (2)	0.0232 (6)
H4	0.4739	−0.0132	0.6973	0.028*
C5	0.1888 (4)	−0.1184 (4)	0.6983 (2)	0.0266 (7)
H5	0.2246	−0.2167	0.7292	0.032*
C6	−0.0094 (4)	−0.0972 (3)	0.6714 (2)	0.0256 (7)
H6	−0.1092	−0.1828	0.6830	0.031*
C7	−0.0681 (4)	0.0460 (3)	0.6277 (2)	0.0229 (6)
H7	−0.2055	0.0597	0.6083	0.028*
C7a	0.0811 (4)	0.1661 (3)	0.6141 (2)	0.0199 (6)
O2	0.2693 (3)	0.5361 (2)	0.52997 (14)	0.0237 (5)
O3	0.4674 (3)	0.2124 (2)	0.51594 (14)	0.0235 (5)
H3	0.5354	0.2918	0.4957	0.035*
C31	0.5790 (4)	0.4009 (3)	0.6840 (2)	0.0222 (6)
H31A	0.6779	0.3210	0.7035	0.027*
H31B	0.6435	0.4898	0.6503	0.027*
C32	0.5359 (4)	0.4987 (3)	0.7816 (2)	0.0205 (6)
O32	0.3636 (3)	0.5034 (2)	0.78916 (15)	0.0285 (5)
C321	0.7069 (4)	0.5905 (3)	0.8661 (2)	0.0216 (6)
C322	0.9024 (4)	0.6020 (3)	0.8533 (2)	0.0239 (6)
H322	0.9289	0.5461	0.7897	0.029*
C323	1.0577 (4)	0.6935 (4)	0.9317 (2)	0.0263 (7)
H323	1.1908	0.7013	0.9213	0.032*
C324	1.0251 (4)	0.7747 (3)	1.0259 (2)	0.0244 (7)
C325	0.8302 (4)	0.7590 (4)	1.0393 (2)	0.0275 (7)
H325	0.8042	0.8112	1.1038	0.033*
C326	0.6748 (4)	0.6695 (3)	0.9611 (2)	0.0263 (7)
H326	0.5419	0.6610	0.9719	0.032*
C327	1.1965 (4)	0.8748 (4)	1.1100 (2)	0.0320 (7)
H32A	1.3216	0.8330	1.0991	0.048*
H32B	1.1745	0.8543	1.1775	0.048*
H32C	1.2059	1.0028	1.1088	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0199 (12)	0.0170 (11)	0.0287 (14)	0.0077 (9)	0.0018 (10)	0.0087 (10)
C2	0.0265 (15)	0.0147 (13)	0.0184 (14)	0.0050 (11)	0.0040 (12)	0.0028 (11)
C3	0.0219 (14)	0.0163 (13)	0.0219 (15)	0.0086 (11)	0.0055 (12)	0.0037 (11)
C3a	0.0246 (14)	0.0148 (13)	0.0210 (15)	0.0053 (11)	0.0056 (12)	0.0037 (11)
C4	0.0286 (15)	0.0188 (13)	0.0231 (15)	0.0082 (11)	0.0055 (12)	0.0041 (11)
C5	0.0375 (17)	0.0183 (14)	0.0273 (16)	0.0106 (12)	0.0098 (13)	0.0060 (12)
C6	0.0339 (16)	0.0147 (13)	0.0319 (17)	0.0041 (12)	0.0137 (13)	0.0071 (12)
C7	0.0257 (15)	0.0176 (13)	0.0257 (16)	0.0060 (11)	0.0061 (12)	0.0027 (11)
C7a	0.0269 (15)	0.0141 (13)	0.0192 (14)	0.0065 (11)	0.0048 (12)	0.0027 (11)
O2	0.0279 (11)	0.0173 (10)	0.0298 (11)	0.0081 (8)	0.0078 (9)	0.0105 (8)
O3	0.0271 (10)	0.0188 (9)	0.0274 (11)	0.0070 (8)	0.0099 (9)	0.0056 (8)
C31	0.0236 (14)	0.0175 (13)	0.0281 (16)	0.0077 (11)	0.0057 (12)	0.0088 (12)
C32	0.0238 (15)	0.0138 (13)	0.0278 (16)	0.0066 (11)	0.0078 (12)	0.0100 (11)
O32	0.0253 (11)	0.0261 (11)	0.0343 (12)	0.0081 (8)	0.0073 (9)	0.0028 (9)
C321	0.0271 (15)	0.0152 (13)	0.0249 (16)	0.0059 (11)	0.0064 (12)	0.0084 (12)
C322	0.0309 (16)	0.0197 (14)	0.0224 (15)	0.0064 (12)	0.0063 (13)	0.0058 (12)
C323	0.0233 (15)	0.0245 (15)	0.0324 (17)	0.0081 (12)	0.0047 (13)	0.0089 (13)
C324	0.0310 (16)	0.0182 (14)	0.0248 (16)	0.0073 (12)	0.0029 (13)	0.0081 (12)
C325	0.0335 (17)	0.0245 (15)	0.0257 (16)	0.0084 (13)	0.0082 (13)	0.0040 (13)
C326	0.0303 (16)	0.0223 (14)	0.0302 (17)	0.0098 (12)	0.0102 (13)	0.0081 (13)
C327	0.0337 (17)	0.0277 (16)	0.0324 (18)	0.0067 (13)	0.0014 (14)	0.0055 (13)

Geometric parameters (Å, º)

N1—C2	1.317 (3)	C31—C32	1.498 (4)
N1—C7a	1.402 (3)	C31—H31A	0.9900
N1—H1	0.8800	C31—H31B	0.9900
C2—O2	1.235 (3)	C32—O32	1.212 (3)
C2—C3	1.532 (4)	C32—C321	1.475 (4)
C3—O3	1.418 (3)	C321—C322	1.384 (4)
C3—C3a	1.493 (4)	C321—C326	1.387 (4)
C3—C31	1.511 (4)	C322—C323	1.368 (4)
C3a—C4	1.374 (3)	C322—H322	0.9500
C3a—C7a	1.380 (4)	C323—C324	1.384 (4)
C4—C5	1.384 (4)	C323—H323	0.9500
C4—H4	0.9500	C324—C325	1.383 (4)
C5—C6	1.372 (4)	C324—C327	1.492 (4)
C5—H5	0.9500	C325—C326	1.363 (4)
C6—C7	1.388 (4)	C325—H325	0.9500
C6—H6	0.9500	C326—H326	0.9500
C7—C7a	1.363 (4)	C327—H32A	0.9800
C7—H7	0.9500	C327—H32B	0.9800
O3—H3	0.8400	C327—H32C	0.9800
C2—N1—C7a	111.3 (2)	C32—C31—H31A	108.1
C2—N1—H1	124.3	C3—C31—H31A	108.1
C7a—N1—H1	124.3	C32—C31—H31B	108.1
O2—C2—N1	125.9 (2)	C3—C31—H31B	108.1
O2—C2—C3	124.4 (2)	H31A—C31—H31B	107.3
N1—C2—C3	109.4 (2)	O32—C32—C321	121.6 (3)
O3—C3—C3a	108.5 (2)	O32—C32—C31	120.0 (2)
O3—C3—C31	109.6 (2)	C321—C32—C31	118.4 (2)
C3a—C3—C31	117.3 (2)	C322—C321—C326	118.1 (3)
O3—C3—C2	107.0 (2)	C322—C321—C32	121.6 (2)
C3a—C3—C2	101.0 (2)	C326—C321—C32	120.3 (2)
C31—C3—C2	112.9 (2)	C323—C322—C321	120.4 (3)
C4—C3a—C7a	119.7 (2)	C323—C322—H322	119.8
C4—C3a—C3	131.1 (2)	C321—C322—H322	119.8
C7a—C3a—C3	109.0 (2)	C322—C323—C324	121.4 (3)
C3a—C4—C5	118.7 (3)	C322—C323—H323	119.3
C3a—C4—H4	120.6	C324—C323—H323	119.3
C5—C4—H4	120.6	C325—C324—C323	118.0 (3)
C6—C5—C4	120.3 (3)	C325—C324—C327	121.5 (3)
C6—C5—H5	119.9	C323—C324—C327	120.5 (3)
C4—C5—H5	119.9	C326—C325—C324	120.7 (3)
C5—C6—C7	121.7 (3)	C326—C325—H325	119.6
C5—C6—H6	119.1	C324—C325—H325	119.6
C7—C6—H6	119.1	C325—C326—C321	121.3 (3)
C7a—C7—C6	116.7 (2)	C325—C326—H326	119.4
C7a—C7—H7	121.6	C321—C326—H326	119.4
C6—C7—H7	121.6	C324—C327—H32A	109.5
C7—C7a—C3a	122.8 (2)	C324—C327—H32B	109.5
C7—C7a—N1	128.1 (2)	H32A—C327—H32B	109.5
C3a—C7a—N1	109.1 (2)	C324—C327—H32C	109.5
C3—O3—H3	109.5	H32A—C327—H32C	109.5
C32—C31—C3	116.8 (2)	H32B—C327—H32C	109.5
C7a—N1—C2—O2	177.5 (2)	C4—C3a—C7a—N1	−179.1 (2)
C7a—N1—C2—C3	3.2 (3)	C3—C3a—C7a—N1	−3.7 (3)
O2—C2—C3—O3	−66.1 (3)	C2—N1—C7a—C7	−177.6 (3)
N1—C2—C3—O3	108.3 (2)	C2—N1—C7a—C3a	0.3 (3)
O2—C2—C3—C3a	−179.4 (2)	O3—C3—C31—C32	178.0 (2)
N1—C2—C3—C3a	−5.1 (3)	C3a—C3—C31—C32	−57.9 (3)
O2—C2—C3—C31	54.5 (3)	C2—C3—C31—C32	58.9 (3)
N1—C2—C3—C31	−131.1 (2)	C3—C31—C32—O32	−8.3 (3)
O3—C3—C3a—C4	67.6 (4)	C3—C31—C32—C321	172.9 (2)
C31—C3—C3a—C4	−57.1 (4)	O32—C32—C321—C322	−172.7 (2)
C2—C3—C3a—C4	179.8 (3)	C31—C32—C321—C322	6.1 (3)
O3—C3—C3a—C7a	−107.1 (2)	O32—C32—C321—C326	6.8 (4)
C31—C3—C3a—C7a	128.2 (2)	C31—C32—C321—C326	−174.4 (2)
C2—C3—C3a—C7a	5.2 (3)	C326—C321—C322—C323	−1.8 (4)
C7a—C3a—C4—C5	−0.9 (4)	C32—C321—C322—C323	177.7 (2)
C3—C3a—C4—C5	−175.1 (3)	C321—C322—C323—C324	0.8 (4)
C3a—C4—C5—C6	1.9 (4)	C322—C323—C324—C325	0.9 (4)
C4—C5—C6—C7	−1.1 (4)	C322—C323—C324—C327	−179.6 (2)
C5—C6—C7—C7a	−0.8 (4)	C323—C324—C325—C326	−1.5 (4)
C6—C7—C7a—C3a	1.9 (4)	C327—C324—C325—C326	179.0 (2)
C6—C7—C7a—N1	179.5 (3)	C324—C325—C326—C321	0.4 (4)
C4—C3a—C7a—C7	−1.1 (4)	C322—C321—C326—C325	1.2 (4)
C3—C3a—C7a—C7	174.3 (2)	C32—C321—C326—C325	−178.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	1.99	2.838 (3)	162
O3—H3···O2^ii	0.84	1.90	2.729 (3)	169

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

(III) 3-hydroxy-3-[(4-fluorobenzoyl)methyl]indolin-2-one

Crystal data

C16H12FNO3	Z = 2
Mr = 285.27	F(000) = 296
Triclinic, P1	Dx = 1.477 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8858 (7) Å	Cell parameters from 2528 reflections
b = 7.7074 (8) Å	θ = 2.7–26.0°
c = 12.7010 (9) Å	µ = 0.11 mm^−1
α = 98.229 (7)°	T = 120 K
β = 103.667 (7)°	Block, yellow-brown
γ = 96.034 (9)°	0.57 × 0.32 × 0.20 mm
V = 641.43 (10) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2528 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 2.7°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.939, Tmax = 0.978	l = −15→15
15674 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 0.3321P] where P = (Fo^2 + 2Fc^2)/3
2528 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0665 (3)	0.3209 (2)	0.57578 (16)	0.0224 (5)
H1	−0.0489	0.3608	0.5540	0.027*
C2	0.2446 (4)	0.4007 (3)	0.57078 (19)	0.0222 (5)
C3	0.4086 (3)	0.2876 (3)	0.61206 (19)	0.0228 (5)
C3a	0.2888 (4)	0.1426 (3)	0.64738 (19)	0.0229 (5)
C4	0.3438 (4)	−0.0031 (3)	0.6909 (2)	0.0263 (6)
H4	0.4815	−0.0205	0.7098	0.032*
C5	0.1951 (4)	−0.1246 (3)	0.7069 (2)	0.0285 (6)
H5	0.2310	−0.2254	0.7379	0.034*
C6	−0.0051 (4)	−0.1001 (3)	0.6779 (2)	0.0267 (6)
H6	−0.1050	−0.1856	0.6889	0.032*
C7	−0.0643 (4)	0.0454 (3)	0.63341 (19)	0.0246 (6)
H7	−0.2022	0.0615	0.6131	0.030*
C7a	0.0861 (4)	0.1654 (3)	0.62006 (18)	0.0219 (5)
O2	0.2742 (2)	0.5356 (2)	0.53256 (13)	0.0266 (4)
O3	0.4692 (2)	0.2111 (2)	0.51872 (13)	0.0241 (4)
H3	0.5364	0.2907	0.5008	0.036*
C31	0.5908 (3)	0.3927 (3)	0.69646 (19)	0.0231 (5)
H31A	0.6845	0.3096	0.7220	0.028*
H31B	0.6612	0.4749	0.6597	0.028*
C32	0.5497 (3)	0.4983 (3)	0.7951 (2)	0.0222 (5)
O32	0.3775 (2)	0.5030 (2)	0.80313 (14)	0.0295 (4)
C321	0.7247 (4)	0.5995 (3)	0.88164 (19)	0.0232 (5)
C322	0.9199 (4)	0.6077 (3)	0.8692 (2)	0.0251 (6)
H322	0.9440	0.5450	0.8046	0.030*
C323	1.0783 (4)	0.7057 (3)	0.9494 (2)	0.0281 (6)
H323	1.2120	0.7133	0.9407	0.034*
C324	1.0393 (4)	0.7919 (3)	1.0418 (2)	0.0296 (6)
F34	1.1973 (2)	0.8857 (2)	1.12187 (12)	0.0411 (4)
C325	0.8506 (4)	0.7859 (3)	1.0593 (2)	0.0324 (6)
H325	0.8291	0.8462	1.1253	0.039*
C326	0.6933 (4)	0.6889 (3)	0.9776 (2)	0.0291 (6)
H326	0.5601	0.6830	0.9870	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0212 (11)	0.0214 (10)	0.0256 (11)	0.0051 (8)	0.0063 (9)	0.0055 (8)
C2	0.0254 (13)	0.0216 (12)	0.0182 (12)	0.0025 (10)	0.0054 (10)	0.0000 (10)
C3	0.0235 (13)	0.0233 (13)	0.0225 (13)	0.0047 (10)	0.0072 (10)	0.0041 (10)
C3a	0.0257 (13)	0.0212 (13)	0.0221 (12)	0.0039 (10)	0.0076 (10)	0.0018 (10)
C4	0.0283 (14)	0.0248 (13)	0.0266 (13)	0.0067 (11)	0.0081 (11)	0.0027 (10)
C5	0.0376 (15)	0.0230 (13)	0.0261 (13)	0.0051 (11)	0.0091 (12)	0.0057 (11)
C6	0.0298 (14)	0.0242 (13)	0.0250 (13)	−0.0013 (11)	0.0088 (11)	0.0015 (10)
C7	0.0234 (13)	0.0263 (13)	0.0220 (13)	0.0019 (10)	0.0045 (10)	0.0010 (10)
C7a	0.0274 (13)	0.0207 (12)	0.0167 (12)	0.0022 (10)	0.0061 (10)	0.0005 (9)
O2	0.0261 (10)	0.0247 (9)	0.0309 (10)	0.0033 (7)	0.0090 (8)	0.0086 (8)
O3	0.0249 (9)	0.0239 (9)	0.0245 (9)	0.0029 (7)	0.0095 (7)	0.0022 (7)
C31	0.0211 (13)	0.0241 (13)	0.0235 (13)	0.0035 (10)	0.0041 (10)	0.0051 (10)
C32	0.0222 (13)	0.0199 (12)	0.0272 (13)	0.0040 (10)	0.0085 (10)	0.0079 (10)
O32	0.0254 (10)	0.0330 (10)	0.0287 (10)	0.0046 (8)	0.0061 (8)	0.0015 (8)
C321	0.0232 (13)	0.0223 (13)	0.0243 (13)	0.0039 (10)	0.0048 (10)	0.0064 (10)
C322	0.0255 (13)	0.0273 (13)	0.0223 (13)	0.0023 (10)	0.0058 (10)	0.0056 (10)
C323	0.0231 (13)	0.0326 (14)	0.0293 (14)	0.0022 (11)	0.0075 (11)	0.0074 (11)
C324	0.0274 (14)	0.0276 (14)	0.0273 (14)	0.0002 (11)	−0.0037 (11)	0.0040 (11)
F34	0.0312 (9)	0.0495 (10)	0.0314 (9)	−0.0054 (7)	−0.0031 (7)	−0.0028 (7)
C325	0.0334 (15)	0.0330 (15)	0.0275 (14)	0.0055 (12)	0.0048 (12)	−0.0012 (12)
C326	0.0273 (14)	0.0295 (14)	0.0312 (14)	0.0070 (11)	0.0085 (11)	0.0036 (11)

Geometric parameters (Å, º)

N1—C2	1.333 (3)	O3—H3	0.8203
N1—C7a	1.400 (3)	C31—C32	1.495 (3)
N1—H1	0.8800	C31—H31A	0.9900
C2—O2	1.227 (3)	C31—H31B	0.9900
C2—C3	1.539 (3)	C32—O32	1.217 (3)
C3—O3	1.419 (3)	C32—C321	1.483 (3)
C3—C3a	1.501 (3)	C321—C322	1.386 (3)
C3—C31	1.511 (3)	C321—C326	1.387 (3)
C3a—C4	1.371 (3)	C322—C323	1.371 (4)
C3a—C7a	1.393 (3)	C322—H322	0.9500
C4—C5	1.385 (3)	C323—C324	1.362 (4)
C4—H4	0.9500	C323—H323	0.9500
C5—C6	1.381 (4)	C324—F34	1.357 (3)
C5—H5	0.9500	C324—C325	1.366 (4)
C6—C7	1.383 (3)	C325—C326	1.373 (4)
C6—H6	0.9500	C325—H325	0.9500
C7—C7a	1.372 (3)	C326—H326	0.9500
C7—H7	0.9500
C2—N1—C7a	111.5 (2)	C3a—C7a—N1	109.4 (2)
C2—N1—H1	124.3	C3—O3—H3	107.0
C7a—N1—H1	124.3	C32—C31—C3	116.11 (19)
O2—C2—N1	126.4 (2)	C32—C31—H31A	108.3
O2—C2—C3	124.5 (2)	C3—C31—H31A	108.3
N1—C2—C3	108.9 (2)	C32—C31—H31B	108.3
O3—C3—C3a	107.67 (18)	C3—C31—H31B	108.3
O3—C3—C31	109.31 (18)	H31A—C31—H31B	107.4
C3a—C3—C31	117.5 (2)	O32—C32—C321	121.2 (2)
O3—C3—C2	106.85 (18)	O32—C32—C31	120.9 (2)
C3a—C3—C2	101.44 (18)	C321—C32—C31	118.0 (2)
C31—C3—C2	113.37 (19)	C322—C321—C326	118.8 (2)
C4—C3a—C7a	119.7 (2)	C322—C321—C32	121.7 (2)
C4—C3a—C3	131.6 (2)	C326—C321—C32	119.5 (2)
C7a—C3a—C3	108.5 (2)	C323—C322—C321	120.5 (2)
C3a—C4—C5	118.8 (2)	C323—C322—H322	119.8
C3a—C4—H4	120.6	C321—C322—H322	119.8
C5—C4—H4	120.6	C324—C323—C322	118.4 (2)
C6—C5—C4	120.4 (2)	C324—C323—H323	120.8
C6—C5—H5	119.8	C322—C323—H323	120.8
C4—C5—H5	119.8	F34—C324—C323	118.1 (2)
C5—C6—C7	121.8 (2)	F34—C324—C325	118.3 (2)
C5—C6—H6	119.1	C323—C324—C325	123.6 (2)
C7—C6—H6	119.1	C324—C325—C326	117.3 (2)
C7a—C7—C6	116.7 (2)	C324—C325—H325	121.4
C7a—C7—H7	121.6	C326—C325—H325	121.4
C6—C7—H7	121.6	C325—C326—C321	121.4 (2)
C7—C7a—C3a	122.5 (2)	C325—C326—H326	119.3
C7—C7a—N1	128.0 (2)	C321—C326—H326	119.3
C7a—N1—C2—O2	177.4 (2)	C4—C3a—C7a—N1	−179.1 (2)
C7a—N1—C2—C3	2.2 (3)	C3—C3a—C7a—N1	−3.7 (3)
O2—C2—C3—O3	−66.8 (3)	C2—N1—C7a—C7	−177.0 (2)
N1—C2—C3—O3	108.6 (2)	C2—N1—C7a—C3a	0.9 (3)
O2—C2—C3—C3a	−179.4 (2)	O3—C3—C31—C32	173.64 (18)
N1—C2—C3—C3a	−4.1 (2)	C3a—C3—C31—C32	−63.4 (3)
O2—C2—C3—C31	53.7 (3)	C2—C3—C31—C32	54.6 (3)
N1—C2—C3—C31	−131.0 (2)	C3—C31—C32—O32	−2.9 (3)
O3—C3—C3a—C4	67.2 (3)	C3—C31—C32—C321	178.3 (2)
C31—C3—C3a—C4	−56.6 (3)	O32—C32—C321—C322	−174.3 (2)
C2—C3—C3a—C4	179.2 (2)	C31—C32—C321—C322	4.6 (3)
O3—C3—C3a—C7a	−107.4 (2)	O32—C32—C321—C326	5.5 (3)
C31—C3—C3a—C7a	128.7 (2)	C31—C32—C321—C326	−175.6 (2)
C2—C3—C3a—C7a	4.6 (2)	C326—C321—C322—C323	−1.4 (4)
C7a—C3a—C4—C5	−0.1 (3)	C32—C321—C322—C323	178.5 (2)
C3—C3a—C4—C5	−174.3 (2)	C321—C322—C323—C324	1.0 (4)
C3a—C4—C5—C6	0.9 (3)	C322—C323—C324—F34	178.7 (2)
C4—C5—C6—C7	−0.6 (4)	C322—C323—C324—C325	0.2 (4)
C5—C6—C7—C7a	−0.5 (3)	F34—C324—C325—C326	−179.5 (2)
C6—C7—C7a—C3a	1.3 (3)	C323—C324—C325—C326	−0.9 (4)
C6—C7—C7a—N1	179.0 (2)	C324—C325—C326—C321	0.6 (4)
C4—C3a—C7a—C7	−1.0 (4)	C322—C321—C326—C325	0.6 (4)
C3—C3a—C7a—C7	174.4 (2)	C32—C321—C326—C325	−179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	1.99	2.842 (2)	163
O3—H3···O2^ii	0.82	1.93	2.746 (2)	172
C325—H325···Cg1^iii	0.95	2.69	3.614 (3)	164

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

(IV) 3-hydroxy-3-[(4-chlorobenzoyl)methyl]indolin-2-one

Crystal data

C16H12ClNO3	Z = 2
Mr = 301.72	F(000) = 312
Triclinic, P1	Dx = 1.513 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.987 (2) Å	Cell parameters from 2720 reflections
b = 7.689 (4) Å	θ = 3.1–26.0°
c = 12.907 (4) Å	µ = 0.30 mm^−1
α = 99.30 (3)°	T = 120 K
β = 101.82 (4)°	Plate, yellow-brown
γ = 96.33 (3)°	0.34 × 0.22 × 0.10 mm
V = 662.4 (5) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2604 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.1°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.920, Tmax = 0.971	l = −15→15
2604 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.4161P] where P = (Fo^2 + 2Fc^2)/3
2604 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0637 (3)	0.3242 (2)	0.57555 (15)	0.0198 (4)
H1	−0.0486	0.3652	0.5571	0.024*
C2	0.2389 (3)	0.4025 (3)	0.56735 (18)	0.0187 (5)
C3	0.3969 (3)	0.2882 (3)	0.60392 (18)	0.0182 (5)
C3a	0.2787 (3)	0.1435 (3)	0.63915 (18)	0.0195 (5)
C4	0.3314 (4)	−0.0039 (3)	0.67840 (18)	0.0219 (5)
H4	0.4654	−0.0236	0.6918	0.026*
C5	0.1862 (4)	−0.1234 (3)	0.69815 (19)	0.0241 (5)
H5	0.2208	−0.2246	0.7272	0.029*
C6	−0.0086 (4)	−0.0960 (3)	0.67581 (19)	0.0238 (5)
H6	−0.1066	−0.1792	0.6898	0.029*
C7	−0.0648 (3)	0.0495 (3)	0.63360 (18)	0.0218 (5)
H7	−0.1994	0.0665	0.6165	0.026*
C7a	0.0821 (3)	0.1679 (3)	0.61746 (17)	0.0191 (5)
O2	0.2681 (2)	0.5370 (2)	0.52970 (13)	0.0219 (4)
O3	0.4575 (2)	0.2122 (2)	0.51023 (12)	0.0210 (4)
H3	0.5498	0.2915	0.5020	0.032*
C31	0.5768 (3)	0.3936 (3)	0.68514 (18)	0.0201 (5)
H31A	0.6705	0.3103	0.7047	0.024*
H31B	0.6426	0.4799	0.6496	0.024*
C32	0.5399 (3)	0.4941 (3)	0.78720 (19)	0.0200 (5)
O32	0.3728 (2)	0.5017 (2)	0.79844 (13)	0.0268 (4)
C321	0.7157 (3)	0.5886 (3)	0.87034 (18)	0.0199 (5)
C322	0.9053 (4)	0.5893 (3)	0.85359 (19)	0.0223 (5)
H322	0.9243	0.5245	0.7882	0.027*
C323	1.0668 (4)	0.6823 (3)	0.9300 (2)	0.0240 (5)
H323	1.1962	0.6835	0.9175	0.029*
C324	1.0370 (4)	0.7728 (3)	1.02429 (19)	0.0228 (5)
Cl34	1.24115 (9)	0.88843 (8)	1.11917 (5)	0.03051 (19)
C325	0.8504 (4)	0.7723 (3)	1.0448 (2)	0.0258 (5)
H325	0.8327	0.8346	1.1112	0.031*
C326	0.6909 (4)	0.6798 (3)	0.96712 (19)	0.0243 (5)
H326	0.5617	0.6784	0.9801	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0132 (9)	0.0232 (10)	0.0244 (10)	0.0049 (8)	0.0046 (8)	0.0063 (8)
C2	0.0168 (11)	0.0205 (12)	0.0178 (11)	0.0033 (9)	0.0032 (9)	0.0016 (9)
C3	0.0159 (11)	0.0196 (12)	0.0209 (12)	0.0057 (9)	0.0061 (9)	0.0040 (9)
C3a	0.0169 (11)	0.0209 (12)	0.0206 (12)	0.0041 (9)	0.0052 (9)	0.0013 (9)
C4	0.0212 (12)	0.0215 (12)	0.0229 (12)	0.0073 (10)	0.0042 (10)	0.0027 (9)
C5	0.0286 (13)	0.0195 (12)	0.0264 (13)	0.0065 (10)	0.0086 (11)	0.0059 (10)
C6	0.0243 (13)	0.0215 (12)	0.0261 (13)	0.0001 (10)	0.0098 (10)	0.0029 (10)
C7	0.0185 (12)	0.0232 (12)	0.0232 (12)	0.0018 (10)	0.0064 (10)	0.0015 (10)
C7a	0.0201 (12)	0.0209 (12)	0.0162 (11)	0.0046 (9)	0.0041 (9)	0.0021 (9)
O2	0.0167 (8)	0.0229 (9)	0.0280 (9)	0.0044 (7)	0.0049 (7)	0.0094 (7)
O3	0.0168 (8)	0.0223 (8)	0.0243 (9)	0.0022 (7)	0.0082 (7)	0.0011 (7)
C31	0.0161 (11)	0.0232 (12)	0.0221 (12)	0.0057 (9)	0.0042 (9)	0.0061 (10)
C32	0.0190 (12)	0.0183 (11)	0.0248 (12)	0.0043 (9)	0.0059 (10)	0.0076 (9)
O32	0.0161 (9)	0.0337 (10)	0.0296 (10)	0.0056 (7)	0.0062 (7)	0.0007 (8)
C321	0.0181 (12)	0.0193 (12)	0.0225 (12)	0.0044 (9)	0.0028 (10)	0.0060 (9)
C322	0.0207 (12)	0.0268 (12)	0.0202 (12)	0.0057 (10)	0.0058 (10)	0.0035 (10)
C323	0.0173 (12)	0.0282 (13)	0.0284 (13)	0.0046 (10)	0.0060 (10)	0.0088 (10)
C324	0.0203 (12)	0.0217 (12)	0.0237 (12)	0.0011 (10)	−0.0010 (10)	0.0057 (10)
Cl34	0.0247 (3)	0.0338 (4)	0.0277 (3)	−0.0007 (3)	−0.0012 (3)	0.0030 (3)
C325	0.0266 (13)	0.0273 (13)	0.0228 (13)	0.0064 (11)	0.0060 (10)	0.0008 (10)
C326	0.0204 (12)	0.0270 (13)	0.0280 (13)	0.0075 (10)	0.0086 (10)	0.0053 (10)

Geometric parameters (Å, º)

N1—C2	1.336 (3)	O3—H3	0.8726
N1—C7a	1.403 (3)	C31—C32	1.501 (3)
N1—H1	0.8800	C31—H31A	0.9900
C2—O2	1.227 (3)	C31—H31B	0.9900
C2—C3	1.532 (3)	C32—O32	1.212 (3)
C3—O3	1.421 (3)	C32—C321	1.483 (3)
C3—C3a	1.497 (3)	C321—C326	1.384 (3)
C3—C31	1.516 (3)	C321—C322	1.385 (3)
C3a—C4	1.370 (3)	C322—C323	1.376 (3)
C3a—C7a	1.384 (3)	C322—H322	0.9500
C4—C5	1.384 (3)	C323—C324	1.368 (4)
C4—H4	0.9500	C323—H323	0.9500
C5—C6	1.380 (3)	C324—C325	1.382 (4)
C5—H5	0.9500	C324—Cl34	1.726 (3)
C6—C7	1.381 (3)	C325—C326	1.375 (4)
C6—H6	0.9500	C325—H325	0.9500
C7—C7a	1.367 (3)	C326—H326	0.9500
C7—H7	0.9500
C2—N1—C7a	111.1 (2)	C3a—C7a—N1	109.5 (2)
C2—N1—H1	124.4	C3—O3—H3	105.8
C7a—N1—H1	124.4	C32—C31—C3	116.39 (19)
O2—C2—N1	126.0 (2)	C32—C31—H31A	108.2
O2—C2—C3	125.0 (2)	C3—C31—H31A	108.2
N1—C2—C3	108.88 (19)	C32—C31—H31B	108.2
O3—C3—C3a	108.34 (18)	C3—C31—H31B	108.2
O3—C3—C31	108.62 (18)	H31A—C31—H31B	107.3
C3a—C3—C31	117.46 (19)	O32—C32—C321	122.2 (2)
O3—C3—C2	106.75 (18)	O32—C32—C31	120.8 (2)
C3a—C3—C2	101.63 (18)	C321—C32—C31	117.0 (2)
C31—C3—C2	113.39 (19)	C326—C321—C322	118.7 (2)
C4—C3a—C7a	119.8 (2)	C326—C321—C32	119.6 (2)
C4—C3a—C3	131.3 (2)	C322—C321—C32	121.7 (2)
C7a—C3a—C3	108.7 (2)	C323—C322—C321	121.2 (2)
C3a—C4—C5	118.9 (2)	C323—C322—H322	119.4
C3a—C4—H4	120.6	C321—C322—H322	119.4
C5—C4—H4	120.6	C324—C323—C322	118.6 (2)
C6—C5—C4	120.1 (2)	C324—C323—H323	120.7
C6—C5—H5	119.9	C322—C323—H323	120.7
C4—C5—H5	119.9	C323—C324—C325	121.9 (2)
C5—C6—C7	121.6 (2)	C323—C324—Cl34	118.0 (2)
C5—C6—H6	119.2	C325—C324—Cl34	120.2 (2)
C7—C6—H6	119.2	C326—C325—C324	118.6 (2)
C7a—C7—C6	117.0 (2)	C326—C325—H325	120.7
C7a—C7—H7	121.5	C324—C325—H325	120.7
C6—C7—H7	121.5	C325—C326—C321	121.0 (2)
C7—C7a—C3a	122.4 (2)	C325—C326—H326	119.5
C7—C7a—N1	128.0 (2)	C321—C326—H326	119.5
C7a—N1—C2—O2	177.1 (2)	C4—C3a—C7a—N1	−178.4 (2)
C7a—N1—C2—C3	1.8 (3)	C3—C3a—C7a—N1	−3.1 (3)
O2—C2—C3—O3	−65.3 (3)	C2—N1—C7a—C7	−177.4 (2)
N1—C2—C3—O3	110.0 (2)	C2—N1—C7a—C3a	0.8 (3)
O2—C2—C3—C3a	−178.7 (2)	O3—C3—C31—C32	176.17 (17)
N1—C2—C3—C3a	−3.4 (2)	C3a—C3—C31—C32	−60.5 (3)
O2—C2—C3—C31	54.3 (3)	C2—C3—C31—C32	57.7 (3)
N1—C2—C3—C31	−130.4 (2)	C3—C31—C32—O32	−6.3 (3)
O3—C3—C3a—C4	66.2 (3)	C3—C31—C32—C321	176.27 (19)
C31—C3—C3a—C4	−57.3 (3)	O32—C32—C321—C326	4.1 (3)
C2—C3—C3a—C4	178.4 (2)	C31—C32—C321—C326	−178.5 (2)
O3—C3—C3a—C7a	−108.4 (2)	O32—C32—C321—C322	−175.4 (2)
C31—C3—C3a—C7a	128.2 (2)	C31—C32—C321—C322	2.0 (3)
C2—C3—C3a—C7a	3.8 (2)	C326—C321—C322—C323	−1.6 (3)
C7a—C3a—C4—C5	−1.6 (3)	C32—C321—C322—C323	177.9 (2)
C3—C3a—C4—C5	−175.7 (2)	C321—C322—C323—C324	0.9 (4)
C3a—C4—C5—C6	1.7 (4)	C322—C323—C324—C325	0.4 (4)
C4—C5—C6—C7	0.0 (4)	C322—C323—C324—Cl34	179.96 (18)
C5—C6—C7—C7a	−1.6 (3)	C323—C324—C325—C326	−0.9 (4)
C6—C7—C7a—C3a	1.7 (3)	Cl34—C324—C325—C326	179.56 (18)
C6—C7—C7a—N1	179.7 (2)	C324—C325—C326—C321	0.1 (4)
C4—C3a—C7a—C7	−0.1 (4)	C322—C321—C326—C325	1.1 (3)
C3—C3a—C7a—C7	175.2 (2)	C32—C321—C326—C325	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	2.00	2.843 (3)	160
O3—H3···O2^ii	0.87	1.88	2.752 (3)	174
C31—H31B···O2^ii	0.99	2.50	3.276 (3)	135
C323—H323···O32^iii	0.95	2.51	3.281 (4)	138
C325—H325···Cg1^iv	0.95	2.97	3.890 (3)	164

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

(V) 3-[(4-bromobenzoyl)methyl]-3-hydroxyindolin-2-one

Crystal data

C16H12BrNO3	Z = 2
Mr = 346.18	F(000) = 348
Triclinic, P1	Dx = 1.701 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.016 (3) Å	Cell parameters from 2800 reflections
b = 7.7349 (12) Å	θ = 2.7–26.5°
c = 13.052 (6) Å	µ = 3.05 mm^−1
α = 99.69 (3)°	T = 120 K
β = 101.51 (4)°	Block, yellow-brown
γ = 96.70 (3)°	0.46 × 0.25 × 0.22 mm
V = 675.8 (4) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2800 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2215 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 9.091 pixels mm^-1	θmax = 26.5°, θmin = 2.7°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.385, Tmax = 0.553	l = −16→16
18834 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 0.5649P] where P = (Fo^2 + 2Fc^2)/3
2800 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0634 (4)	0.3254 (3)	0.5748 (2)	0.0164 (6)
H1	−0.0485	0.3656	0.5572	0.020*
C2	0.2370 (5)	0.4033 (4)	0.5659 (2)	0.0156 (7)
C3	0.3941 (5)	0.2896 (4)	0.6001 (2)	0.0156 (6)
C3a	0.2761 (5)	0.1450 (4)	0.6348 (2)	0.0162 (7)
C4	0.3294 (5)	−0.0031 (4)	0.6718 (2)	0.0175 (7)
H4	0.4619	−0.0243	0.6820	0.021*
C5	0.1851 (5)	−0.1201 (4)	0.6938 (3)	0.0204 (7)
H5	0.2196	−0.2201	0.7225	0.025*
C6	−0.0073 (5)	−0.0928 (4)	0.6743 (3)	0.0213 (7)
H6	−0.1044	−0.1755	0.6891	0.026*
C7	−0.0637 (5)	0.0520 (4)	0.6337 (2)	0.0190 (7)
H7	−0.1976	0.0691	0.6186	0.023*
C7a	0.0825 (4)	0.1698 (4)	0.6163 (2)	0.0152 (6)
O2	0.2665 (3)	0.5371 (3)	0.52888 (17)	0.0188 (5)
O3	0.4545 (3)	0.2144 (3)	0.50721 (16)	0.0172 (5)
H3	0.5298	0.2904	0.4862	0.026*
C31	0.5741 (4)	0.3945 (4)	0.6810 (2)	0.0163 (7)
H31A	0.6667	0.3113	0.6992	0.020*
H31B	0.6402	0.4810	0.6464	0.020*
C32	0.5389 (5)	0.4934 (4)	0.7827 (2)	0.0177 (7)
O32	0.3737 (3)	0.5021 (3)	0.79489 (18)	0.0242 (5)
C321	0.7157 (5)	0.5854 (4)	0.8656 (2)	0.0180 (7)
C322	0.9027 (5)	0.5873 (4)	0.8470 (3)	0.0205 (7)
H322	0.9199	0.5252	0.7811	0.025*
C323	1.0650 (5)	0.6781 (4)	0.9229 (3)	0.0204 (7)
H323	1.1935	0.6796	0.9097	0.025*
C324	1.0375 (5)	0.7661 (4)	1.0177 (3)	0.0203 (7)
Br34	1.26306 (5)	0.88941 (4)	1.11883 (3)	0.02613 (13)
C325	0.8537 (5)	0.7636 (4)	1.0397 (3)	0.0225 (7)
H325	0.8376	0.8232	1.1065	0.027*
C326	0.6939 (5)	0.6729 (4)	0.9628 (3)	0.0206 (7)
H326	0.5660	0.6704	0.9769	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0163 (14)	0.0131 (12)	0.0209 (14)	0.0047 (10)	0.0034 (11)	0.0062 (10)
C2	0.0196 (17)	0.0142 (15)	0.0131 (15)	0.0013 (12)	0.0051 (13)	0.0017 (12)
C3	0.0172 (16)	0.0142 (14)	0.0160 (16)	0.0023 (12)	0.0043 (13)	0.0040 (12)
C3a	0.0194 (17)	0.0151 (14)	0.0125 (15)	−0.0008 (12)	0.0041 (13)	−0.0003 (12)
C4	0.0207 (18)	0.0157 (15)	0.0156 (16)	0.0058 (13)	0.0021 (13)	0.0024 (12)
C5	0.0288 (19)	0.0120 (14)	0.0211 (17)	0.0035 (13)	0.0054 (14)	0.0051 (13)
C6	0.028 (2)	0.0135 (15)	0.0229 (18)	0.0005 (13)	0.0103 (15)	0.0020 (13)
C7	0.0203 (18)	0.0165 (15)	0.0198 (17)	0.0021 (13)	0.0061 (13)	0.0004 (13)
C7a	0.0184 (17)	0.0129 (14)	0.0143 (15)	0.0030 (12)	0.0031 (13)	0.0031 (12)
O2	0.0203 (12)	0.0151 (11)	0.0224 (12)	0.0034 (9)	0.0046 (9)	0.0078 (9)
O3	0.0194 (12)	0.0159 (10)	0.0173 (11)	0.0004 (9)	0.0088 (9)	0.0025 (9)
C31	0.0157 (17)	0.0155 (14)	0.0189 (16)	0.0030 (12)	0.0042 (13)	0.0066 (12)
C32	0.0230 (19)	0.0102 (14)	0.0224 (17)	0.0036 (12)	0.0070 (14)	0.0073 (12)
O32	0.0190 (13)	0.0274 (12)	0.0255 (13)	0.0050 (10)	0.0065 (10)	0.0005 (10)
C321	0.0221 (18)	0.0125 (15)	0.0223 (18)	0.0064 (13)	0.0071 (14)	0.0068 (13)
C322	0.0266 (19)	0.0168 (15)	0.0195 (17)	0.0048 (13)	0.0068 (14)	0.0044 (13)
C323	0.0208 (18)	0.0210 (16)	0.0217 (17)	0.0042 (14)	0.0065 (14)	0.0074 (13)
C324	0.0237 (19)	0.0159 (15)	0.0209 (17)	0.0022 (13)	0.0019 (14)	0.0067 (13)
Br34	0.0285 (2)	0.02281 (18)	0.02227 (19)	−0.00138 (13)	−0.00189 (13)	0.00392 (13)
C325	0.030 (2)	0.0193 (16)	0.0192 (17)	0.0059 (14)	0.0065 (15)	0.0036 (13)
C326	0.0206 (18)	0.0192 (16)	0.0234 (18)	0.0055 (13)	0.0061 (14)	0.0047 (13)

Geometric parameters (Å, º)

N1—C2	1.330 (4)	O3—H3	0.8599
N1—C7a	1.409 (4)	C31—C32	1.497 (4)
N1—H1	0.8800	C31—H31A	0.9900
C2—O2	1.227 (3)	C31—H31B	0.9900
C2—C3	1.532 (4)	C32—O32	1.209 (4)
C3—O3	1.419 (4)	C32—C321	1.488 (4)
C3—C3a	1.498 (4)	C321—C322	1.380 (5)
C3—C31	1.519 (4)	C321—C326	1.380 (4)
C3a—C7a	1.373 (4)	C322—C323	1.378 (5)
C3a—C4	1.378 (4)	C322—H322	0.9500
C4—C5	1.384 (4)	C323—C324	1.368 (5)
C4—H4	0.9500	C323—H323	0.9500
C5—C6	1.371 (5)	C324—C325	1.375 (5)
C5—H5	0.9500	C324—Br34	1.883 (3)
C6—C7	1.383 (4)	C325—C326	1.373 (5)
C6—H6	0.9500	C325—H325	0.9500
C7—C7a	1.371 (4)	C326—H326	0.9500
C7—H7	0.9500
C2—N1—C7a	110.9 (3)	C3a—C7a—N1	109.7 (3)
C2—N1—H1	124.5	C3—O3—H3	112.4
C7a—N1—H1	124.5	C32—C31—C3	116.6 (3)
O2—C2—N1	126.1 (3)	C32—C31—H31A	108.1
O2—C2—C3	124.7 (3)	C3—C31—H31A	108.1
N1—C2—C3	109.0 (2)	C32—C31—H31B	108.1
O3—C3—C3a	108.4 (2)	C3—C31—H31B	108.1
O3—C3—C31	108.5 (2)	H31A—C31—H31B	107.3
C3a—C3—C31	117.0 (3)	O32—C32—C321	121.9 (3)
O3—C3—C2	107.4 (2)	O32—C32—C31	121.1 (3)
C3a—C3—C2	101.5 (2)	C321—C32—C31	117.0 (3)
C31—C3—C2	113.4 (2)	C322—C321—C326	118.8 (3)
C7a—C3a—C4	120.0 (3)	C322—C321—C32	121.3 (3)
C7a—C3a—C3	108.8 (3)	C326—C321—C32	119.9 (3)
C4—C3a—C3	130.9 (3)	C323—C322—C321	120.9 (3)
C3a—C4—C5	118.4 (3)	C323—C322—H322	119.6
C3a—C4—H4	120.8	C321—C322—H322	119.6
C5—C4—H4	120.8	C324—C323—C322	118.7 (3)
C6—C5—C4	120.5 (3)	C324—C323—H323	120.6
C6—C5—H5	119.8	C322—C323—H323	120.6
C4—C5—H5	119.8	C323—C324—C325	121.9 (3)
C5—C6—C7	121.7 (3)	C323—C324—Br34	117.3 (3)
C5—C6—H6	119.2	C325—C324—Br34	120.8 (3)
C7—C6—H6	119.2	C326—C325—C324	118.5 (3)
C7a—C7—C6	116.9 (3)	C326—C325—H325	120.8
C7a—C7—H7	121.5	C324—C325—H325	120.8
C6—C7—H7	121.5	C325—C326—C321	121.3 (3)
C7—C7a—C3a	122.4 (3)	C325—C326—H326	119.4
C7—C7a—N1	127.9 (3)	C321—C326—H326	119.4
C7a—N1—C2—O2	177.3 (3)	C4—C3a—C7a—N1	−177.5 (3)
C7a—N1—C2—C3	2.3 (3)	C3—C3a—C7a—N1	−2.1 (3)
O2—C2—C3—O3	−64.7 (4)	C2—N1—C7a—C7	−177.9 (3)
N1—C2—C3—O3	110.4 (3)	C2—N1—C7a—C3a	−0.2 (3)
O2—C2—C3—C3a	−178.4 (3)	O3—C3—C31—C32	176.6 (2)
N1—C2—C3—C3a	−3.3 (3)	C3a—C3—C31—C32	−60.4 (4)
O2—C2—C3—C31	55.2 (4)	C2—C3—C31—C32	57.3 (3)
N1—C2—C3—C31	−129.7 (3)	C3—C31—C32—O32	−6.7 (4)
O3—C3—C3a—C7a	−109.7 (3)	C3—C31—C32—C321	175.6 (2)
C31—C3—C3a—C7a	127.2 (3)	O32—C32—C321—C322	−174.2 (3)
C2—C3—C3a—C7a	3.2 (3)	C31—C32—C321—C322	3.5 (4)
O3—C3—C3a—C4	65.1 (4)	O32—C32—C321—C326	4.9 (5)
C31—C3—C3a—C4	−58.0 (4)	C31—C32—C321—C326	−177.4 (3)
C2—C3—C3a—C4	178.0 (3)	C326—C321—C322—C323	−1.4 (4)
C7a—C3a—C4—C5	−2.7 (4)	C32—C321—C322—C323	177.7 (3)
C3—C3a—C4—C5	−177.0 (3)	C321—C322—C323—C324	0.3 (5)
C3a—C4—C5—C6	2.9 (5)	C322—C323—C324—C325	1.2 (5)
C4—C5—C6—C7	−0.7 (5)	C322—C323—C324—Br34	−179.7 (2)
C5—C6—C7—C7a	−1.6 (5)	C323—C324—C325—C326	−1.4 (5)
C6—C7—C7a—C3a	1.8 (5)	Br34—C324—C325—C326	179.5 (2)
C6—C7—C7a—N1	179.3 (3)	C324—C325—C326—C321	0.2 (5)
C4—C3a—C7a—C7	0.4 (5)	C322—C321—C326—C325	1.2 (5)
C3—C3a—C7a—C7	175.8 (3)	C32—C321—C326—C325	−178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	2.01	2.851 (4)	160
O3—H3···O2^ii	0.86	1.90	2.746 (3)	167
C31—H31B···O2^ii	0.99	2.49	3.257 (4)	134
C323—H323···O32^iii	0.95	2.49	3.271 (4)	140

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

(VI) 3-hydroxy-3-[(4-nitrobenzoyl)methyl]indolin-2-one

Crystal data

C16H12N2O5	Z = 2
Mr = 312.28	F(000) = 324
Triclinic, P1	Dx = 1.519 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.026 (1) Å	Cell parameters from 2683 reflections
b = 7.598 (3) Å	θ = 3.7–26.0°
c = 13.365 (4) Å	µ = 0.12 mm^−1
α = 97.54 (3)°	T = 120 K
β = 102.67 (2)°	Block, yellow-brown
γ = 96.46 (2)°	0.27 × 0.17 × 0.12 mm
V = 682.7 (3) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2683 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.096
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.7°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.970, Tmax = 0.986	l = −16→16
19392 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 0.3346P] where P = (Fo^2 + 2Fc^2)/3
2683 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0655 (3)	0.3211 (3)	0.57180 (18)	0.0253 (6)
H1	−0.0461	0.3633	0.5525	0.030*
C2	0.2408 (4)	0.4009 (4)	0.5653 (2)	0.0261 (7)
C3	0.3976 (4)	0.2833 (4)	0.6037 (2)	0.0237 (7)
C3a	0.2778 (4)	0.1366 (4)	0.6373 (2)	0.0251 (7)
C4	0.3303 (4)	−0.0124 (4)	0.6790 (2)	0.0293 (7)
H4	0.4642	−0.0312	0.6960	0.035*
C5	0.1825 (4)	−0.1341 (4)	0.6955 (2)	0.0307 (7)
H5	0.2153	−0.2370	0.7251	0.037*
C6	−0.0116 (4)	−0.1072 (4)	0.6695 (2)	0.0306 (7)
H6	−0.1106	−0.1931	0.6808	0.037*
C7	−0.0659 (4)	0.0408 (4)	0.6277 (2)	0.0266 (7)
H7	−0.2001	0.0585	0.6095	0.032*
C7a	0.0817 (4)	0.1612 (4)	0.6134 (2)	0.0243 (7)
O2	0.2716 (3)	0.5375 (3)	0.52828 (15)	0.0277 (5)
O3	0.4593 (3)	0.2086 (3)	0.51530 (15)	0.0272 (5)
H3	0.5378	0.2901	0.4996	0.041*
C31	0.5773 (4)	0.3853 (4)	0.6834 (2)	0.0254 (7)
H31A	0.6677	0.2986	0.7044	0.030*
H31B	0.6466	0.4714	0.6491	0.030*
C32	0.5422 (4)	0.4864 (4)	0.7794 (2)	0.0245 (7)
O32	0.3772 (3)	0.4957 (3)	0.79150 (16)	0.0317 (5)
C321	0.7201 (4)	0.5813 (4)	0.8598 (2)	0.0236 (7)
C322	0.9068 (4)	0.5751 (4)	0.8453 (2)	0.0263 (7)
H322	0.9243	0.5075	0.7838	0.032*
C323	1.0697 (4)	0.6664 (4)	0.9194 (2)	0.0284 (7)
H323	1.1991	0.6630	0.9095	0.034*
C324	1.0392 (4)	0.7618 (4)	1.0072 (2)	0.0252 (7)
C325	0.8545 (4)	0.7693 (4)	1.0248 (2)	0.0302 (7)
H325	0.8380	0.8353	1.0870	0.036*
C326	0.6945 (4)	0.6790 (4)	0.9502 (2)	0.0299 (7)
H326	0.5654	0.6833	0.9604	0.036*
N34	1.2127 (4)	0.8555 (3)	1.08607 (19)	0.0311 (6)
O33	1.3745 (3)	0.8340 (4)	1.07444 (19)	0.0526 (7)
O34	1.1852 (3)	0.9505 (4)	1.16011 (18)	0.0506 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0228 (13)	0.0272 (14)	0.0266 (14)	0.0059 (10)	0.0047 (10)	0.0068 (11)
C2	0.0305 (17)	0.0285 (17)	0.0195 (16)	0.0046 (13)	0.0084 (13)	0.0006 (13)
C3	0.0250 (16)	0.0227 (16)	0.0250 (16)	0.0058 (12)	0.0079 (12)	0.0040 (13)
C3a	0.0269 (16)	0.0238 (16)	0.0235 (16)	0.0043 (12)	0.0063 (12)	−0.0015 (13)
C4	0.0288 (17)	0.0306 (18)	0.0287 (17)	0.0083 (14)	0.0050 (13)	0.0054 (14)
C5	0.0407 (19)	0.0257 (17)	0.0283 (17)	0.0092 (14)	0.0093 (14)	0.0082 (14)
C6	0.0334 (18)	0.0301 (18)	0.0300 (18)	0.0007 (14)	0.0143 (14)	0.0031 (14)
C7	0.0248 (16)	0.0288 (17)	0.0262 (16)	0.0033 (13)	0.0079 (13)	0.0012 (13)
C7a	0.0285 (16)	0.0225 (16)	0.0220 (15)	0.0055 (12)	0.0065 (12)	0.0017 (12)
O2	0.0277 (11)	0.0257 (12)	0.0315 (12)	0.0037 (9)	0.0078 (9)	0.0101 (10)
O3	0.0273 (11)	0.0266 (11)	0.0278 (12)	0.0018 (9)	0.0102 (9)	0.0009 (9)
C31	0.0235 (15)	0.0294 (17)	0.0238 (16)	0.0056 (12)	0.0053 (12)	0.0051 (13)
C32	0.0255 (16)	0.0230 (16)	0.0264 (17)	0.0050 (12)	0.0065 (13)	0.0072 (13)
O32	0.0267 (12)	0.0350 (13)	0.0326 (13)	0.0063 (9)	0.0075 (9)	0.0002 (10)
C321	0.0221 (15)	0.0243 (16)	0.0253 (16)	0.0038 (12)	0.0057 (12)	0.0067 (13)
C322	0.0287 (17)	0.0270 (17)	0.0246 (16)	0.0061 (13)	0.0082 (13)	0.0039 (13)
C323	0.0260 (16)	0.0322 (18)	0.0290 (17)	0.0059 (13)	0.0095 (13)	0.0055 (14)
C324	0.0247 (16)	0.0257 (17)	0.0239 (16)	0.0038 (12)	0.0025 (13)	0.0046 (13)
C325	0.0304 (17)	0.0355 (18)	0.0246 (17)	0.0095 (14)	0.0064 (13)	0.0001 (14)
C326	0.0254 (16)	0.0358 (18)	0.0297 (18)	0.0090 (13)	0.0079 (13)	0.0031 (14)
N34	0.0290 (15)	0.0376 (16)	0.0254 (15)	0.0073 (12)	0.0037 (11)	0.0032 (12)
O33	0.0250 (13)	0.0722 (18)	0.0498 (16)	0.0065 (12)	0.0042 (11)	−0.0203 (13)
O34	0.0376 (14)	0.0720 (18)	0.0334 (14)	0.0064 (12)	0.0059 (11)	−0.0172 (13)

Geometric parameters (Å, º)

N1—C2	1.336 (4)	C31—C32	1.490 (4)
N1—C7a	1.406 (4)	C31—H31A	0.9900
N1—H1	0.8800	C31—H31B	0.9900
C2—O2	1.225 (3)	C32—O32	1.214 (3)
C2—C3	1.539 (4)	C32—C321	1.497 (4)
C3—O3	1.418 (3)	C321—C322	1.372 (4)
C3—C3a	1.496 (4)	C321—C326	1.390 (4)
C3—C31	1.518 (4)	C322—C323	1.385 (4)
C3a—C4	1.378 (4)	C322—H322	0.9500
C3a—C7a	1.385 (4)	C323—C324	1.367 (4)
C4—C5	1.385 (4)	C323—H323	0.9500
C4—H4	0.9500	C324—C325	1.375 (4)
C5—C6	1.377 (4)	C324—N34	1.466 (4)
C5—H5	0.9500	C325—C326	1.372 (4)
C6—C7	1.375 (4)	C325—H325	0.9500
C6—H6	0.9500	C326—H326	0.9500
C7—C7a	1.367 (4)	N34—O33	1.206 (3)
C7—H7	0.9500	N34—O34	1.211 (3)
O3—H3	0.8600
C2—N1—C7a	111.5 (2)	C32—C31—C3	117.0 (2)
C2—N1—H1	124.2	C32—C31—H31A	108.0
C7a—N1—H1	124.2	C3—C31—H31A	108.0
O2—C2—N1	126.3 (3)	C32—C31—H31B	108.0
O2—C2—C3	125.1 (3)	C3—C31—H31B	108.0
N1—C2—C3	108.4 (2)	H31A—C31—H31B	107.3
O3—C3—C3a	108.2 (2)	O32—C32—C31	121.9 (3)
O3—C3—C31	108.5 (2)	O32—C32—C321	121.0 (3)
C3a—C3—C31	117.1 (2)	C31—C32—C321	117.0 (2)
O3—C3—C2	106.7 (2)	C322—C321—C326	119.7 (3)
C3a—C3—C2	101.7 (2)	C322—C321—C32	121.2 (3)
C31—C3—C2	114.0 (2)	C326—C321—C32	119.1 (2)
C4—C3a—C7a	119.8 (3)	C321—C322—C323	120.6 (3)
C4—C3a—C3	131.1 (3)	C321—C322—H322	119.7
C7a—C3a—C3	108.9 (2)	C323—C322—H322	119.7
C3a—C4—C5	118.2 (3)	C324—C323—C322	118.2 (3)
C3a—C4—H4	120.9	C324—C323—H323	120.9
C5—C4—H4	120.9	C322—C323—H323	120.9
C6—C5—C4	120.6 (3)	C323—C324—C325	122.7 (3)
C6—C5—H5	119.7	C323—C324—N34	117.8 (3)
C4—C5—H5	119.7	C325—C324—N34	119.4 (3)
C7—C6—C5	121.8 (3)	C326—C325—C324	118.3 (3)
C7—C6—H6	119.1	C326—C325—H325	120.8
C5—C6—H6	119.1	C324—C325—H325	120.8
C7a—C7—C6	117.0 (3)	C325—C326—C321	120.4 (3)
C7a—C7—H7	121.5	C325—C326—H326	119.8
C6—C7—H7	121.5	C321—C326—H326	119.8
C7—C7a—C3a	122.6 (3)	O33—N34—O34	123.4 (3)
C7—C7a—N1	128.2 (3)	O33—N34—C324	118.8 (3)
C3a—C7a—N1	109.2 (2)	O34—N34—C324	117.7 (2)
C3—O3—H3	108.3
C7a—N1—C2—O2	176.7 (3)	C2—N1—C7a—C7	−177.2 (3)
C7a—N1—C2—C3	1.6 (3)	C2—N1—C7a—C3a	1.2 (3)
O2—C2—C3—O3	−65.4 (4)	O3—C3—C31—C32	175.4 (2)
N1—C2—C3—O3	109.8 (2)	C3a—C3—C31—C32	−61.8 (3)
O2—C2—C3—C3a	−178.7 (3)	C2—C3—C31—C32	56.7 (3)
N1—C2—C3—C3a	−3.5 (3)	C3—C31—C32—O32	−4.0 (4)
O2—C2—C3—C31	54.4 (4)	C3—C31—C32—C321	177.7 (2)
N1—C2—C3—C31	−130.4 (2)	O32—C32—C321—C322	−178.2 (3)
O3—C3—C3a—C4	67.6 (4)	C31—C32—C321—C322	0.1 (4)
C31—C3—C3a—C4	−55.3 (4)	O32—C32—C321—C326	1.0 (4)
C2—C3—C3a—C4	179.8 (3)	C31—C32—C321—C326	179.3 (3)
O3—C3—C3a—C7a	−108.0 (3)	C326—C321—C322—C323	−0.5 (4)
C31—C3—C3a—C7a	129.1 (3)	C32—C321—C322—C323	178.7 (3)
C2—C3—C3a—C7a	4.2 (3)	C321—C322—C323—C324	0.3 (4)
C7a—C3a—C4—C5	0.1 (4)	C322—C323—C324—C325	0.4 (4)
C3—C3a—C4—C5	−175.1 (3)	C322—C323—C324—N34	178.9 (2)
C3a—C4—C5—C6	0.8 (4)	C323—C324—C325—C326	−0.9 (4)
C4—C5—C6—C7	−0.7 (5)	N34—C324—C325—C326	−179.4 (3)
C5—C6—C7—C7a	−0.3 (4)	C324—C325—C326—C321	0.6 (5)
C6—C7—C7a—C3a	1.3 (4)	C322—C321—C326—C325	0.0 (4)
C6—C7—C7a—N1	179.5 (3)	C32—C321—C326—C325	−179.2 (3)
C4—C3a—C7a—C7	−1.2 (4)	C323—C324—N34—O33	−5.6 (4)
C3—C3a—C7a—C7	175.0 (3)	C325—C324—N34—O33	173.0 (3)
C4—C3a—C7a—N1	−179.8 (3)	C323—C324—N34—O34	174.6 (3)
C3—C3a—C7a—N1	−3.6 (3)	C325—C324—N34—O34	−6.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	1.99	2.848 (3)	164
O3—H3···O2^ii	0.86	1.90	2.756 (3)	175
C31—H31B···O2^ii	0.99	2.55	3.330 (4)	135
C323—H323···O32^iii	0.95	2.52	3.308 (4)	140
C326—H326···O33^iv	0.95	2.49	3.304 (4)	143

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

(VII) 3-hydroxy-3-(2-thienylcarbonylmethyl)indolin-2-one

Crystal data

C14H11NO3S	Z = 2
Mr = 273.30	F(000) = 284
Triclinic, P1	Dx = 1.508 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5958 (7) Å	Cell parameters from 2355 reflections
b = 7.9577 (14) Å	θ = 3.3–26.0°
c = 12.045 (3) Å	µ = 0.27 mm^−1
α = 78.51 (2)°	T = 120 K
β = 76.555 (13)°	Block, yellow-brown
γ = 84.559 (15)°	0.41 × 0.23 × 0.14 mm
V = 601.8 (2) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2355 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.3°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.885, Tmax = 0.963	l = −14→14
14010 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.4932P] where P = (Fo^2 + 2Fc^2)/3
2355 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	1.0025 (3)	0.3142 (2)	0.42275 (17)	0.0200 (4)
H1	1.1019	0.3477	0.4499	0.024*
C2	0.8172 (3)	0.3972 (3)	0.4230 (2)	0.0210 (5)
C3	0.6810 (3)	0.2928 (3)	0.3776 (2)	0.0193 (5)
C3a	0.8353 (3)	0.1527 (3)	0.3393 (2)	0.0193 (5)
C4	0.8135 (4)	0.0171 (3)	0.2889 (2)	0.0244 (5)
H4	0.6880	0.0061	0.2657	0.029*
C5	0.9794 (4)	−0.1041 (3)	0.2727 (2)	0.0257 (6)
H5	0.9691	−0.1970	0.2358	0.031*
C6	1.1574 (4)	−0.0898 (3)	0.3097 (2)	0.0250 (6)
H6	1.2674	−0.1753	0.2995	0.030*
C7	1.1820 (4)	0.0461 (3)	0.3616 (2)	0.0222 (5)
H7	1.3054	0.0553	0.3874	0.027*
C7a	1.0186 (3)	0.1660 (3)	0.3735 (2)	0.0196 (5)
O2	0.7576 (2)	0.5298 (2)	0.46143 (15)	0.0237 (4)
O3	0.5315 (2)	0.21687 (19)	0.47558 (14)	0.0219 (4)
H3	0.4640	0.2931	0.5071	0.033*
C31	0.5704 (3)	0.4007 (3)	0.2889 (2)	0.0210 (5)
H31A	0.4999	0.3233	0.2567	0.025*
H31B	0.4609	0.4756	0.3290	0.025*
C32	0.7085 (4)	0.5113 (3)	0.1902 (2)	0.0210 (5)
O32	0.8952 (2)	0.5129 (2)	0.18401 (15)	0.0269 (4)
S321	0.75166 (10)	0.75473 (8)	−0.00821 (6)	0.0300 (2)
C322	0.6065 (4)	0.6202 (3)	0.1052 (2)	0.0213 (5)
C323	0.3989 (4)	0.6329 (3)	0.0999 (2)	0.0227 (5)
H323	0.2941	0.5674	0.1545	0.027*
C324	0.3607 (4)	0.7549 (3)	0.0035 (2)	0.0269 (6)
H324	0.2270	0.7815	−0.0141	0.032*
C325	0.5370 (4)	0.8295 (3)	−0.0608 (2)	0.0300 (6)
H325	0.5400	0.9151	−0.1285	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0191 (10)	0.0182 (10)	0.0255 (11)	−0.0004 (8)	−0.0075 (8)	−0.0082 (8)
C2	0.0226 (12)	0.0185 (12)	0.0210 (13)	−0.0012 (9)	−0.0033 (10)	−0.0033 (10)
C3	0.0184 (11)	0.0174 (11)	0.0226 (13)	0.0007 (9)	−0.0040 (9)	−0.0060 (10)
C3a	0.0209 (11)	0.0151 (11)	0.0216 (12)	0.0001 (9)	−0.0040 (9)	−0.0040 (9)
C4	0.0257 (12)	0.0227 (12)	0.0266 (14)	−0.0027 (10)	−0.0062 (10)	−0.0073 (10)
C5	0.0308 (13)	0.0170 (12)	0.0291 (14)	−0.0013 (10)	−0.0031 (11)	−0.0077 (10)
C6	0.0268 (13)	0.0170 (12)	0.0284 (14)	0.0018 (10)	−0.0019 (11)	−0.0040 (10)
C7	0.0214 (12)	0.0200 (12)	0.0228 (13)	−0.0005 (9)	−0.0019 (10)	−0.0017 (10)
C7a	0.0222 (12)	0.0160 (11)	0.0197 (12)	−0.0019 (9)	−0.0020 (10)	−0.0041 (9)
O2	0.0232 (8)	0.0197 (8)	0.0307 (10)	0.0009 (7)	−0.0062 (7)	−0.0108 (7)
O3	0.0222 (8)	0.0186 (8)	0.0239 (9)	0.0011 (6)	−0.0024 (7)	−0.0055 (7)
C31	0.0200 (11)	0.0198 (12)	0.0242 (13)	0.0015 (9)	−0.0061 (10)	−0.0061 (10)
C32	0.0247 (13)	0.0165 (11)	0.0243 (13)	0.0015 (9)	−0.0065 (10)	−0.0097 (10)
O32	0.0220 (9)	0.0252 (9)	0.0335 (10)	−0.0008 (7)	−0.0063 (7)	−0.0049 (8)
S321	0.0298 (4)	0.0278 (4)	0.0303 (4)	−0.0033 (3)	−0.0051 (3)	−0.0014 (3)
C322	0.0242 (12)	0.0176 (11)	0.0222 (13)	−0.0005 (9)	−0.0025 (10)	−0.0073 (10)
C323	0.0270 (12)	0.0197 (12)	0.0228 (13)	0.0016 (10)	−0.0061 (10)	−0.0081 (10)
C324	0.0318 (14)	0.0236 (13)	0.0282 (14)	0.0032 (10)	−0.0103 (11)	−0.0094 (11)
C325	0.0399 (15)	0.0245 (13)	0.0268 (14)	0.0024 (11)	−0.0119 (12)	−0.0041 (11)

Geometric parameters (Å, º)

N1—C2	1.333 (3)	C7—C7a	1.371 (3)
N1—C7a	1.407 (3)	C7—H7	0.9500
N1—H1	0.8800	O3—H3	0.8202
C2—O2	1.230 (3)	C31—C32	1.500 (3)
C2—C3	1.533 (3)	C31—H31A	0.9900
C3—O3	1.420 (3)	C31—H31B	0.9900
C3—C3a	1.504 (3)	C32—O32	1.218 (3)
C3—C31	1.514 (3)	C32—C322	1.452 (3)
C3a—C4	1.372 (3)	S321—C325	1.693 (3)
C3a—C7a	1.385 (3)	S321—C322	1.713 (2)
C4—C5	1.393 (3)	C322—C323	1.379 (3)
C4—H4	0.9500	C323—C324	1.412 (3)
C5—C6	1.371 (3)	C323—H323	0.9500
C5—H5	0.9500	C324—C325	1.354 (4)
C6—C7	1.392 (3)	C324—H324	0.9500
C6—H6	0.9500	C325—H325	0.9500
C2—N1—C7a	111.20 (19)	C7—C7a—C3a	122.7 (2)
C2—N1—H1	124.4	C7—C7a—N1	128.1 (2)
C7a—N1—H1	124.4	C3a—C7a—N1	109.22 (19)
O2—C2—N1	126.0 (2)	C3—O3—H3	108.9
O2—C2—C3	124.7 (2)	C32—C31—C3	115.01 (18)
N1—C2—C3	109.14 (19)	C32—C31—H31A	108.5
O3—C3—C3a	107.73 (17)	C3—C31—H31A	108.5
O3—C3—C31	109.67 (17)	C32—C31—H31B	108.5
C3a—C3—C31	117.8 (2)	C3—C31—H31B	108.5
O3—C3—C2	106.60 (18)	H31A—C31—H31B	107.5
C3a—C3—C2	101.11 (17)	O32—C32—C322	122.1 (2)
C31—C3—C2	113.09 (18)	O32—C32—C31	121.5 (2)
C4—C3a—C7a	120.0 (2)	C322—C32—C31	116.4 (2)
C4—C3a—C3	131.0 (2)	C325—S321—C322	91.38 (12)
C7a—C3a—C3	108.8 (2)	C323—C322—C32	129.0 (2)
C3a—C4—C5	118.6 (2)	C323—C322—S321	111.50 (18)
C3a—C4—H4	120.7	C32—C322—S321	119.49 (17)
C5—C4—H4	120.7	C322—C323—C324	111.9 (2)
C6—C5—C4	120.2 (2)	C322—C323—H323	124.0
C6—C5—H5	119.9	C324—C323—H323	124.0
C4—C5—H5	119.9	C325—C324—C323	112.2 (2)
C5—C6—C7	122.0 (2)	C325—C324—H324	123.9
C5—C6—H6	119.0	C323—C324—H324	123.9
C7—C6—H6	119.0	C324—C325—S321	113.1 (2)
C7a—C7—C6	116.5 (2)	C324—C325—H325	123.5
C7a—C7—H7	121.8	S321—C325—H325	123.5
C6—C7—H7	121.8
C7a—N1—C2—O2	179.3 (2)	C3—C3a—C7a—C7	173.2 (2)
C7a—N1—C2—C3	4.4 (3)	C4—C3a—C7a—N1	−179.7 (2)
O2—C2—C3—O3	−69.5 (3)	C3—C3a—C7a—N1	−5.1 (3)
N1—C2—C3—O3	105.6 (2)	C2—N1—C7a—C7	−177.8 (2)
O2—C2—C3—C3a	178.1 (2)	C2—N1—C7a—C3a	0.4 (3)
N1—C2—C3—C3a	−6.9 (2)	O3—C3—C31—C32	170.28 (18)
O2—C2—C3—C31	51.1 (3)	C3a—C3—C31—C32	−66.1 (3)
N1—C2—C3—C31	−133.8 (2)	C2—C3—C31—C32	51.5 (3)
O3—C3—C3a—C4	69.3 (3)	C3—C31—C32—O32	−0.5 (3)
C31—C3—C3a—C4	−55.3 (3)	C3—C31—C32—C322	−178.3 (2)
C2—C3—C3a—C4	−179.1 (2)	O32—C32—C322—C323	179.8 (2)
O3—C3—C3a—C7a	−104.5 (2)	C31—C32—C322—C323	−2.4 (4)
C31—C3—C3a—C7a	130.8 (2)	O32—C32—C322—S321	0.5 (3)
C2—C3—C3a—C7a	7.1 (2)	C31—C32—C322—S321	178.26 (16)
C7a—C3a—C4—C5	−0.5 (3)	C325—S321—C322—C323	0.89 (19)
C3—C3a—C4—C5	−173.8 (2)	C325—S321—C322—C32	−179.7 (2)
C3a—C4—C5—C6	1.9 (4)	C32—C322—C323—C324	179.8 (2)
C4—C5—C6—C7	−1.6 (4)	S321—C322—C323—C324	−0.8 (3)
C5—C6—C7—C7a	−0.3 (3)	C322—C323—C324—C325	0.3 (3)
C6—C7—C7a—C3a	1.8 (3)	C323—C324—C325—S321	0.4 (3)
C6—C7—C7a—N1	179.8 (2)	C322—S321—C325—C324	−0.7 (2)
C4—C3a—C7a—C7	−1.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	2.00	2.843 (3)	160
O3—H3···O2^ii	0.82	1.96	2.736 (2)	158
C7—H7···O3^iii	0.95	2.58	3.443 (3)	151
C31—H31B···O2^ii	0.99	2.59	3.382 (3)	137

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