6-Chloro-3-hydr­oxy-3-(2-oxoprop­yl)indolin-2-one

In the crystal structure of the title compound, C₁₁H₁₀ClNO₃, an indole derivative, weak inter­molecular hydrogen bonds cause the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.102
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C8      ..       5.11 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O3      ..       3.26 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               2391
           Count of symmetry unique reflns         1413
           Completeness (_total/calc)            169.21%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       978
           Fraction of Friedel pairs measured     0.692
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

6-chloro-3-hydroxy-3-(2-oxopropyl)indolin-2-one

Crystal data

C11H10ClNO3	F(000) = 496
Mr = 239.03	Dx = 1.451 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4278 reflections
a = 6.5958 (6) Å	θ = 2.8–28.3°
b = 7.8459 (8) Å	µ = 0.34 mm^−1
c = 21.202 (2) Å	T = 298 K
V = 1097.19 (18) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer	2277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −8→8
6687 measured reflections	k = −8→10
2391 independent reflections	l = −15→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.1036P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
2391 reflections	Δρmax = 0.24 e Å^−3
147 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.1455 (3)	0.4145 (3)	0.24001 (9)	0.0463 (4)
C2	0.3309 (3)	0.4916 (3)	0.23110 (9)	0.0506 (5)
H2	0.3652	0.5368	0.1920	0.061*
C3	0.4660 (3)	0.5011 (3)	0.28126 (8)	0.0441 (4)
H3	0.5919	0.5526	0.2760	0.053*
C4	0.4118 (3)	0.4338 (2)	0.33866 (8)	0.0334 (3)
C5	0.2202 (3)	0.3612 (2)	0.34619 (8)	0.0350 (4)
C6	0.0830 (3)	0.3482 (3)	0.29766 (9)	0.0425 (4)
H6	−0.0437	0.2982	0.3030	0.051*
C7	0.5239 (2)	0.4247 (2)	0.40058 (7)	0.0322 (3)
C8	0.3605 (3)	0.3475 (2)	0.44421 (8)	0.0330 (3)
C9	0.6055 (3)	0.5942 (2)	0.42433 (9)	0.0430 (4)
H9A	0.6725	0.5755	0.4645	0.052*
H9B	0.7069	0.6350	0.3948	0.052*
C10	0.4475 (3)	0.7301 (2)	0.43270 (9)	0.0457 (5)
C11	0.5196 (5)	0.9100 (3)	0.44026 (13)	0.0713 (7)
H11A	0.4271	0.9858	0.4194	0.107*
H11B	0.6520	0.9214	0.4219	0.107*
H11C	0.5260	0.9379	0.4843	0.107*
Cl1	−0.01856 (10)	0.39308 (10)	0.17596 (3)	0.0687 (2)
N1	0.1981 (2)	0.3078 (2)	0.40939 (7)	0.0376 (3)
H1A	0.0929	0.2583	0.4240	0.045*
O1	0.68321 (18)	0.30239 (18)	0.39526 (6)	0.0405 (3)
H1	0.7337	0.2860	0.4301	0.061*
O2	0.38586 (19)	0.31770 (17)	0.50041 (6)	0.0396 (3)
O3	0.2694 (3)	0.6960 (2)	0.43441 (8)	0.0632 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0537 (10)	0.0481 (10)	0.0371 (9)	0.0043 (9)	−0.0117 (8)	−0.0043 (8)
C2	0.0592 (11)	0.0589 (12)	0.0336 (9)	−0.0019 (11)	−0.0002 (8)	0.0075 (9)
C3	0.0469 (10)	0.0475 (10)	0.0379 (9)	−0.0062 (9)	0.0036 (8)	0.0057 (8)
C4	0.0354 (8)	0.0310 (8)	0.0339 (8)	−0.0014 (7)	−0.0011 (6)	0.0005 (6)
C5	0.0378 (8)	0.0324 (8)	0.0347 (8)	−0.0018 (7)	0.0011 (7)	−0.0012 (6)
C6	0.0392 (8)	0.0438 (10)	0.0446 (9)	−0.0033 (8)	−0.0048 (7)	−0.0020 (7)
C7	0.0320 (7)	0.0319 (7)	0.0325 (7)	−0.0015 (7)	0.0010 (6)	0.0032 (6)
C8	0.0350 (8)	0.0278 (7)	0.0363 (8)	0.0027 (7)	0.0031 (7)	0.0003 (6)
C9	0.0449 (9)	0.0380 (9)	0.0461 (9)	−0.0106 (8)	−0.0045 (7)	0.0007 (8)
C10	0.0668 (13)	0.0350 (9)	0.0353 (9)	−0.0045 (9)	−0.0037 (8)	0.0009 (7)
C11	0.103 (2)	0.0352 (10)	0.0758 (15)	−0.0071 (14)	0.0056 (16)	−0.0032 (10)
Cl1	0.0722 (4)	0.0868 (4)	0.0470 (3)	−0.0011 (3)	−0.0238 (3)	−0.0041 (3)
N1	0.0344 (7)	0.0412 (8)	0.0370 (7)	−0.0075 (6)	0.0023 (6)	0.0050 (7)
O1	0.0378 (6)	0.0469 (7)	0.0367 (6)	0.0076 (6)	0.0044 (5)	0.0042 (6)
O2	0.0409 (6)	0.0457 (7)	0.0322 (6)	0.0030 (6)	0.0022 (5)	0.0050 (5)
O3	0.0609 (10)	0.0462 (8)	0.0827 (11)	0.0075 (8)	−0.0039 (9)	−0.0082 (8)

Geometric parameters (Å, º)

C1—C2	1.377 (3)	C7—C8	1.544 (2)
C1—C6	1.391 (3)	C8—O2	1.226 (2)
C1—Cl1	1.7445 (19)	C8—N1	1.338 (2)
C2—C3	1.389 (3)	C9—C10	1.502 (3)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.374 (2)	C9—H9B	0.9700
C3—H3	0.9300	C10—O3	1.205 (3)
C4—C5	1.395 (2)	C10—C11	1.498 (3)
C4—C7	1.508 (2)	C11—H11A	0.9600
C5—C6	1.374 (3)	C11—H11B	0.9600
C5—N1	1.412 (2)	C11—H11C	0.9600
C6—H6	0.9300	N1—H1A	0.8531
C7—O1	1.428 (2)	O1—H1	0.8200
C7—C9	1.520 (2)
C2—C1—C6	123.23 (17)	C9—C7—C8	113.08 (14)
C2—C1—Cl1	119.08 (15)	O2—C8—N1	126.98 (16)
C6—C1—Cl1	117.67 (16)	O2—C8—C7	124.17 (15)
C1—C2—C3	119.22 (18)	N1—C8—C7	108.65 (14)
C1—C2—H2	120.4	C10—C9—C7	114.48 (15)
C3—C2—H2	120.4	C10—C9—H9A	108.6
C4—C3—C2	119.36 (18)	C7—C9—H9A	108.6
C4—C3—H3	120.3	C10—C9—H9B	108.6
C2—C3—H3	120.3	C7—C9—H9B	108.6
C3—C4—C5	119.60 (16)	H9A—C9—H9B	107.6
C3—C4—C7	131.42 (16)	O3—C10—C11	121.0 (2)
C5—C4—C7	108.97 (14)	O3—C10—C9	121.48 (18)
C6—C5—C4	122.77 (17)	C11—C10—C9	117.5 (2)
C6—C5—N1	128.35 (16)	C10—C11—H11A	109.5
C4—C5—N1	108.88 (15)	C10—C11—H11B	109.5
C5—C6—C1	115.78 (17)	H11A—C11—H11B	109.5
C5—C6—H6	122.1	C10—C11—H11C	109.5
C1—C6—H6	122.1	H11A—C11—H11C	109.5
O1—C7—C4	108.88 (13)	H11B—C11—H11C	109.5
O1—C7—C9	110.69 (13)	C8—N1—C5	111.82 (14)
C4—C7—C9	114.88 (14)	C8—N1—H1A	123.8
O1—C7—C8	107.31 (13)	C5—N1—H1A	124.4
C4—C7—C8	101.41 (13)	C7—O1—H1	109.5
C6—C1—C2—C3	1.6 (3)	C3—C4—C7—C8	174.9 (2)
Cl1—C1—C2—C3	−176.77 (18)	C5—C4—C7—C8	−3.61 (17)
C1—C2—C3—C4	−0.1 (3)	O1—C7—C8—O2	66.2 (2)
C2—C3—C4—C5	−1.8 (3)	C4—C7—C8—O2	−179.70 (16)
C2—C3—C4—C7	179.90 (19)	C9—C7—C8—O2	−56.2 (2)
C3—C4—C5—C6	2.3 (3)	O1—C7—C8—N1	−108.97 (15)
C7—C4—C5—C6	−178.99 (16)	C4—C7—C8—N1	5.15 (17)
C3—C4—C5—N1	−177.66 (17)	C9—C7—C8—N1	128.68 (15)
C7—C4—C5—N1	1.02 (19)	O1—C7—C9—C10	−178.81 (14)
C4—C5—C6—C1	−0.9 (3)	C4—C7—C9—C10	57.4 (2)
N1—C5—C6—C1	179.11 (18)	C8—C7—C9—C10	−58.38 (19)
C2—C1—C6—C5	−1.1 (3)	C7—C9—C10—O3	16.1 (3)
Cl1—C1—C6—C5	177.31 (14)	C7—C9—C10—C11	−165.21 (19)
C3—C4—C7—O1	−72.2 (2)	O2—C8—N1—C5	−179.94 (17)
C5—C4—C7—O1	109.33 (15)	C7—C8—N1—C5	−5.0 (2)
C3—C4—C7—C9	52.6 (3)	C6—C5—N1—C8	−177.40 (17)
C5—C4—C7—C9	−125.91 (16)	C4—C5—N1—C8	2.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.96	2.7510 (18)	162
N1—H1A···O2^ii	0.85	2.19	2.9776 (19)	154
C11—H11C···O3^iii	0.96	2.58	3.235 (3)	126

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+3/2, −z+1.