3-Hy­droxy-3-(2-oxo-2,3-di­hydro-1H-indol-3-yl)-2,3-di­hydro-1H-indol-2-one

The conformation of the title mol­ecule, C₁₆H₁₂N₂O₃, is partly determined by an intra­molecular C=O...π inter­action between one carbonyl group and the five-membered ring of the other indolinone moiety. The crystal packing consists of layers parallel to (001) formed by a combination of N—H...O and O—H...O hydrogen bonds and π–π stacking inter­actions. Both the N—H...O and O—H...O hydrogen bonds generate inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.101
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         37 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

Crystal data

C16H12N2O3	Z = 2
Mr = 280.28	F(000) = 292
Triclinic, P1	Dx = 1.451 Mg m^−3
a = 7.7193 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.6977 (3) Å	Cell parameters from 6334 reflections
c = 9.5907 (4) Å	θ = 4.6–72.4°
α = 90.457 (2)°	µ = 0.84 mm^−1
β = 95.070 (2)°	T = 150 K
γ = 90.627 (2)°	Column, dark yellow-orange
V = 641.34 (4) Å^3	0.14 × 0.07 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2487 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2137 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.4°, θmin = 4.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
Tmin = 0.89, Tmax = 0.96	l = −11→11
8464 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)] = 0.039	Hydrogen site location: mixed
wR(F^2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.3252P] where P = (Fo^2 + 2Fc^2)/3
2487 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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. The hydroxyl hydrogen did not refine satisfactorily although definitely located in a difference map, possibly due to unresolved disorder. Consequently it was placed in a calculated position (SHELXL HFIX 147 instruction) and included as a riding contribution.

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

	x	y	z	Uiso*/Ueq
O1	0.78629 (14)	1.05555 (13)	0.52109 (12)	0.0311 (3)
O2	0.94772 (15)	0.94251 (13)	0.26711 (13)	0.0311 (3)
H2A	1.0265	0.9586	0.3319	0.047*
O3	0.58356 (14)	0.70275 (12)	0.52877 (12)	0.0272 (3)
N1	0.56106 (17)	1.03152 (15)	0.34911 (14)	0.0252 (3)
H1	0.491 (3)	1.105 (3)	0.388 (2)	0.052 (6)*
N2	0.69437 (18)	0.50298 (15)	0.40763 (14)	0.0248 (3)
H2B	0.613 (3)	0.433 (3)	0.423 (2)	0.051 (6)*
C1	0.5182 (2)	0.93711 (17)	0.23090 (16)	0.0243 (3)
C2	0.3649 (2)	0.9328 (2)	0.14575 (18)	0.0306 (4)
H2	0.266 (3)	1.000 (2)	0.162 (2)	0.033 (5)*
C3	0.3529 (2)	0.8279 (2)	0.03503 (19)	0.0341 (4)
H3	0.246 (3)	0.824 (2)	−0.025 (2)	0.042 (6)*
C4	0.4899 (2)	0.7319 (2)	0.01088 (18)	0.0334 (4)
H4	0.474 (3)	0.656 (2)	−0.070 (2)	0.037 (5)*
C5	0.6447 (2)	0.73867 (19)	0.09783 (17)	0.0281 (4)
H5	0.743 (3)	0.672 (2)	0.084 (2)	0.033 (5)*
C6	0.6578 (2)	0.84201 (17)	0.20856 (16)	0.0230 (3)
C7	0.80112 (19)	0.87379 (17)	0.32288 (16)	0.0224 (3)
C8	0.71796 (19)	0.99649 (17)	0.41294 (17)	0.0239 (3)
C9	0.85503 (19)	0.73274 (17)	0.41305 (16)	0.0225 (3)
H9	0.928 (2)	0.7736 (19)	0.5023 (18)	0.022 (4)*
C10	0.69513 (19)	0.64824 (17)	0.45866 (16)	0.0222 (3)
C11	0.8409 (2)	0.47612 (17)	0.33341 (16)	0.0233 (3)
C12	0.8850 (2)	0.34313 (19)	0.26664 (18)	0.0289 (4)
H12	0.812 (3)	0.251 (2)	0.267 (2)	0.033 (5)*
C13	1.0385 (2)	0.3456 (2)	0.20033 (19)	0.0326 (4)
H13	1.073 (3)	0.257 (2)	0.153 (2)	0.039 (5)*
C14	1.1432 (2)	0.4764 (2)	0.20282 (19)	0.0336 (4)
H14	1.251 (3)	0.476 (2)	0.159 (2)	0.039 (5)*
C15	1.0967 (2)	0.6096 (2)	0.27092 (18)	0.0288 (4)
H15	1.169 (2)	0.701 (2)	0.273 (2)	0.031 (5)*
C16	0.94318 (19)	0.60941 (17)	0.33510 (16)	0.0229 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0273 (6)	0.0304 (6)	0.0357 (7)	−0.0045 (5)	0.0043 (5)	−0.0121 (5)
O2	0.0265 (6)	0.0299 (6)	0.0382 (7)	−0.0054 (5)	0.0111 (5)	−0.0011 (5)
O3	0.0281 (6)	0.0223 (5)	0.0331 (6)	0.0003 (4)	0.0133 (5)	−0.0023 (4)
N1	0.0236 (6)	0.0220 (6)	0.0306 (7)	0.0002 (5)	0.0065 (5)	−0.0039 (5)
N2	0.0262 (7)	0.0193 (6)	0.0302 (7)	−0.0027 (5)	0.0102 (5)	−0.0015 (5)
C1	0.0257 (8)	0.0217 (7)	0.0265 (8)	−0.0028 (6)	0.0076 (6)	−0.0003 (6)
C2	0.0259 (8)	0.0344 (9)	0.0321 (9)	0.0018 (7)	0.0057 (7)	0.0022 (7)
C3	0.0291 (8)	0.0430 (10)	0.0297 (9)	−0.0039 (7)	−0.0001 (7)	0.0009 (7)
C4	0.0391 (9)	0.0346 (9)	0.0263 (9)	−0.0015 (7)	0.0021 (7)	−0.0041 (7)
C5	0.0326 (8)	0.0258 (8)	0.0265 (8)	0.0017 (7)	0.0058 (6)	−0.0016 (6)
C6	0.0235 (7)	0.0203 (7)	0.0258 (8)	−0.0031 (6)	0.0058 (6)	0.0016 (6)
C7	0.0202 (7)	0.0195 (7)	0.0283 (8)	−0.0042 (6)	0.0075 (6)	−0.0019 (6)
C8	0.0229 (7)	0.0187 (7)	0.0310 (8)	−0.0052 (6)	0.0086 (6)	−0.0018 (6)
C9	0.0203 (7)	0.0214 (7)	0.0263 (8)	−0.0015 (6)	0.0050 (6)	−0.0033 (6)
C10	0.0233 (7)	0.0203 (7)	0.0235 (7)	−0.0001 (6)	0.0043 (6)	0.0001 (6)
C11	0.0247 (7)	0.0222 (7)	0.0236 (8)	0.0018 (6)	0.0053 (6)	0.0004 (6)
C12	0.0358 (9)	0.0218 (8)	0.0298 (8)	0.0012 (7)	0.0074 (7)	−0.0013 (6)
C13	0.0384 (9)	0.0281 (9)	0.0327 (9)	0.0070 (7)	0.0100 (7)	−0.0042 (7)
C14	0.0296 (9)	0.0364 (9)	0.0367 (9)	0.0052 (7)	0.0127 (7)	−0.0032 (7)
C15	0.0237 (8)	0.0287 (8)	0.0347 (9)	−0.0005 (7)	0.0067 (6)	−0.0019 (7)
C16	0.0226 (7)	0.0213 (7)	0.0250 (7)	0.0010 (6)	0.0030 (6)	−0.0014 (6)

Geometric parameters (Å, º)

O1—C8	1.2275 (19)	C5—C6	1.382 (2)
O2—C7	1.4217 (18)	C5—H5	0.97 (2)
O2—H2A	0.8400	C6—C7	1.509 (2)
O3—C10	1.2348 (18)	C7—C9	1.546 (2)
N1—C8	1.347 (2)	C7—C8	1.548 (2)
N1—C1	1.408 (2)	C9—C16	1.505 (2)
N1—H1	0.94 (2)	C9—C10	1.528 (2)
N2—C10	1.3510 (19)	C9—H9	1.039 (17)
N2—C11	1.4091 (19)	C11—C12	1.378 (2)
N2—H2B	0.90 (3)	C11—C16	1.395 (2)
C1—C2	1.378 (2)	C12—C13	1.394 (2)
C1—C6	1.396 (2)	C12—H12	0.97 (2)
C2—C3	1.391 (3)	C13—C14	1.387 (3)
C2—H2	0.99 (2)	C13—H13	0.95 (2)
C3—C4	1.388 (3)	C14—C15	1.392 (2)
C3—H3	0.97 (2)	C14—H14	0.97 (2)
C4—C5	1.396 (2)	C15—C16	1.383 (2)
C4—H4	1.02 (2)	C15—H15	0.96 (2)
C7—O2—H2A	109.5	O1—C8—N1	126.03 (14)
C8—N1—C1	111.47 (13)	O1—C8—C7	125.72 (14)
C8—N1—H1	120.7 (14)	N1—C8—C7	108.20 (13)
C1—N1—H1	127.6 (14)	C16—C9—C10	102.45 (12)
C10—N2—C11	111.35 (13)	C16—C9—C7	113.88 (13)
C10—N2—H2B	123.3 (14)	C10—C9—C7	110.84 (12)
C11—N2—H2B	125.3 (14)	C16—C9—H9	114.1 (9)
C2—C1—C6	122.38 (15)	C10—C9—H9	108.2 (10)
C2—C1—N1	127.82 (14)	C7—C9—H9	107.2 (9)
C6—C1—N1	109.80 (14)	O3—C10—N2	125.26 (14)
C1—C2—C3	117.15 (16)	O3—C10—C9	126.29 (14)
C1—C2—H2	122.0 (11)	N2—C10—C9	108.44 (13)
C3—C2—H2	120.9 (11)	C12—C11—C16	122.28 (15)
C4—C3—C2	121.50 (16)	C12—C11—N2	128.31 (15)
C4—C3—H3	120.7 (12)	C16—C11—N2	109.41 (13)
C2—C3—H3	117.8 (12)	C11—C12—C13	117.30 (16)
C3—C4—C5	120.50 (16)	C11—C12—H12	120.7 (11)
C3—C4—H4	118.5 (11)	C13—C12—H12	121.9 (11)
C5—C4—H4	121.0 (11)	C14—C13—C12	121.20 (15)
C6—C5—C4	118.51 (15)	C14—C13—H13	118.8 (13)
C6—C5—H5	119.3 (11)	C12—C13—H13	119.9 (13)
C4—C5—H5	122.2 (11)	C13—C14—C15	120.69 (16)
C5—C6—C1	119.95 (15)	C13—C14—H14	120.5 (12)
C5—C6—C7	131.78 (14)	C15—C14—H14	118.8 (12)
C1—C6—C7	108.24 (13)	C16—C15—C14	118.65 (16)
O2—C7—C6	110.72 (12)	C16—C15—H15	120.3 (11)
O2—C7—C9	111.02 (12)	C14—C15—H15	121.0 (11)
C6—C7—C9	114.49 (12)	C15—C16—C11	119.85 (14)
O2—C7—C8	107.89 (12)	C15—C16—C9	131.84 (14)
C6—C7—C8	102.04 (12)	C11—C16—C9	108.31 (13)
C9—C7—C8	110.15 (12)
C8—N1—C1—C2	175.44 (16)	C6—C7—C9—C16	67.76 (16)
C8—N1—C1—C6	−4.44 (19)	C8—C7—C9—C16	−177.95 (12)
C6—C1—C2—C3	0.4 (2)	O2—C7—C9—C10	−173.39 (12)
N1—C1—C2—C3	−179.48 (16)	C6—C7—C9—C10	−47.12 (17)
C1—C2—C3—C4	−0.3 (3)	C8—C7—C9—C10	67.17 (15)
C2—C3—C4—C5	−0.2 (3)	C11—N2—C10—O3	−179.33 (14)
C3—C4—C5—C6	0.4 (3)	C11—N2—C10—C9	1.48 (17)
C4—C5—C6—C1	−0.3 (2)	C16—C9—C10—O3	178.65 (15)
C4—C5—C6—C7	177.50 (16)	C7—C9—C10—O3	−59.5 (2)
C2—C1—C6—C5	−0.1 (2)	C16—C9—C10—N2	−2.16 (16)
N1—C1—C6—C5	179.79 (14)	C7—C9—C10—N2	119.69 (14)
C2—C1—C6—C7	−178.38 (15)	C10—N2—C11—C12	−179.90 (16)
N1—C1—C6—C7	1.50 (17)	C10—N2—C11—C16	−0.08 (18)
C5—C6—C7—O2	68.9 (2)	C16—C11—C12—C13	0.4 (2)
C1—C6—C7—O2	−113.13 (14)	N2—C11—C12—C13	−179.79 (16)
C5—C6—C7—C9	−57.6 (2)	C11—C12—C13—C14	0.6 (3)
C1—C6—C7—C9	120.45 (14)	C12—C13—C14—C15	−0.6 (3)
C5—C6—C7—C8	−176.54 (17)	C13—C14—C15—C16	−0.5 (3)
C1—C6—C7—C8	1.48 (15)	C14—C15—C16—C11	1.5 (2)
C1—N1—C8—O1	−177.15 (15)	C14—C15—C16—C9	−178.43 (16)
C1—N1—C8—C7	5.31 (17)	C12—C11—C16—C15	−1.5 (2)
O2—C7—C8—O1	−65.0 (2)	N2—C11—C16—C15	178.67 (14)
C6—C7—C8—O1	178.37 (15)	C12—C11—C16—C9	178.46 (15)
C9—C7—C8—O1	56.38 (19)	N2—C11—C16—C9	−1.37 (17)
O2—C7—C8—N1	112.59 (14)	C10—C9—C16—C15	−177.95 (17)
C6—C7—C8—N1	−4.09 (15)	C7—C9—C16—C15	62.3 (2)
C9—C7—C8—N1	−126.08 (13)	C10—C9—C16—C11	2.10 (16)
O2—C7—C9—C16	−58.50 (16)	C7—C9—C16—C11	−117.65 (14)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1,C6,C7,C8,N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	0.84	1.93	2.7575 (17)	167
N1—H1···O3^ii	0.94 (2)	1.96 (2)	2.8644 (17)	161 (2)
N2—H2B···O3^iii	0.90 (3)	2.00 (3)	2.8882 (18)	173 (2)
C10—O3···Cg1	1.24 (1)	2.92 (1)	3.0414 (13)	73 (1)

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