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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020739/bq2011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020739/bq2011Isup2.hkl
Contains datablock I

CCDC reference: 651481

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

Computing details top

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 top
Crystal data top
C11H10ClNO3F(000) = 496
Mr = 239.03Dx = 1.451 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4278 reflections
a = 6.5958 (6) Åθ = 2.8–28.3°
b = 7.8459 (8) ŵ = 0.34 mm1
c = 21.202 (2) ÅT = 298 K
V = 1097.19 (18) Å3Block, colorless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 27.0°, θmin = 1.9°
φ and ω scansh = 88
6687 measured reflectionsk = 810
2391 independent reflectionsl = 1527
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.06P)2 + 0.1036P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
2391 reflectionsΔρmax = 0.24 e Å3
147 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (8)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.1455 (3)0.4145 (3)0.24001 (9)0.0463 (4)
C20.3309 (3)0.4916 (3)0.23110 (9)0.0506 (5)
H20.36520.53680.19200.061*
C30.4660 (3)0.5011 (3)0.28126 (8)0.0441 (4)
H30.59190.55260.27600.053*
C40.4118 (3)0.4338 (2)0.33866 (8)0.0334 (3)
C50.2202 (3)0.3612 (2)0.34619 (8)0.0350 (4)
C60.0830 (3)0.3482 (3)0.29766 (9)0.0425 (4)
H60.04370.29820.30300.051*
C70.5239 (2)0.4247 (2)0.40058 (7)0.0322 (3)
C80.3605 (3)0.3475 (2)0.44421 (8)0.0330 (3)
C90.6055 (3)0.5942 (2)0.42433 (9)0.0430 (4)
H9A0.67250.57550.46450.052*
H9B0.70690.63500.39480.052*
C100.4475 (3)0.7301 (2)0.43270 (9)0.0457 (5)
C110.5196 (5)0.9100 (3)0.44026 (13)0.0713 (7)
H11A0.42710.98580.41940.107*
H11B0.65200.92140.42190.107*
H11C0.52600.93790.48430.107*
Cl10.01856 (10)0.39308 (10)0.17596 (3)0.0687 (2)
N10.1981 (2)0.3078 (2)0.40939 (7)0.0376 (3)
H1A0.09290.25830.42400.045*
O10.68321 (18)0.30239 (18)0.39526 (6)0.0405 (3)
H10.73370.28600.43010.061*
O20.38586 (19)0.31770 (17)0.50041 (6)0.0396 (3)
O30.2694 (3)0.6960 (2)0.43441 (8)0.0632 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0537 (10)0.0481 (10)0.0371 (9)0.0043 (9)0.0117 (8)0.0043 (8)
C20.0592 (11)0.0589 (12)0.0336 (9)0.0019 (11)0.0002 (8)0.0075 (9)
C30.0469 (10)0.0475 (10)0.0379 (9)0.0062 (9)0.0036 (8)0.0057 (8)
C40.0354 (8)0.0310 (8)0.0339 (8)0.0014 (7)0.0011 (6)0.0005 (6)
C50.0378 (8)0.0324 (8)0.0347 (8)0.0018 (7)0.0011 (7)0.0012 (6)
C60.0392 (8)0.0438 (10)0.0446 (9)0.0033 (8)0.0048 (7)0.0020 (7)
C70.0320 (7)0.0319 (7)0.0325 (7)0.0015 (7)0.0010 (6)0.0032 (6)
C80.0350 (8)0.0278 (7)0.0363 (8)0.0027 (7)0.0031 (7)0.0003 (6)
C90.0449 (9)0.0380 (9)0.0461 (9)0.0106 (8)0.0045 (7)0.0007 (8)
C100.0668 (13)0.0350 (9)0.0353 (9)0.0045 (9)0.0037 (8)0.0009 (7)
C110.103 (2)0.0352 (10)0.0758 (15)0.0071 (14)0.0056 (16)0.0032 (10)
Cl10.0722 (4)0.0868 (4)0.0470 (3)0.0011 (3)0.0238 (3)0.0041 (3)
N10.0344 (7)0.0412 (8)0.0370 (7)0.0075 (6)0.0023 (6)0.0050 (7)
O10.0378 (6)0.0469 (7)0.0367 (6)0.0076 (6)0.0044 (5)0.0042 (6)
O20.0409 (6)0.0457 (7)0.0322 (6)0.0030 (6)0.0022 (5)0.0050 (5)
O30.0609 (10)0.0462 (8)0.0827 (11)0.0075 (8)0.0039 (9)0.0082 (8)
Geometric parameters (Å, º) top
C1—C21.377 (3)C7—C81.544 (2)
C1—C61.391 (3)C8—O21.226 (2)
C1—Cl11.7445 (19)C8—N11.338 (2)
C2—C31.389 (3)C9—C101.502 (3)
C2—H20.9300C9—H9A0.9700
C3—C41.374 (2)C9—H9B0.9700
C3—H30.9300C10—O31.205 (3)
C4—C51.395 (2)C10—C111.498 (3)
C4—C71.508 (2)C11—H11A0.9600
C5—C61.374 (3)C11—H11B0.9600
C5—N11.412 (2)C11—H11C0.9600
C6—H60.9300N1—H1A0.8531
C7—O11.428 (2)O1—H10.8200
C7—C91.520 (2)
C2—C1—C6123.23 (17)C9—C7—C8113.08 (14)
C2—C1—Cl1119.08 (15)O2—C8—N1126.98 (16)
C6—C1—Cl1117.67 (16)O2—C8—C7124.17 (15)
C1—C2—C3119.22 (18)N1—C8—C7108.65 (14)
C1—C2—H2120.4C10—C9—C7114.48 (15)
C3—C2—H2120.4C10—C9—H9A108.6
C4—C3—C2119.36 (18)C7—C9—H9A108.6
C4—C3—H3120.3C10—C9—H9B108.6
C2—C3—H3120.3C7—C9—H9B108.6
C3—C4—C5119.60 (16)H9A—C9—H9B107.6
C3—C4—C7131.42 (16)O3—C10—C11121.0 (2)
C5—C4—C7108.97 (14)O3—C10—C9121.48 (18)
C6—C5—C4122.77 (17)C11—C10—C9117.5 (2)
C6—C5—N1128.35 (16)C10—C11—H11A109.5
C4—C5—N1108.88 (15)C10—C11—H11B109.5
C5—C6—C1115.78 (17)H11A—C11—H11B109.5
C5—C6—H6122.1C10—C11—H11C109.5
C1—C6—H6122.1H11A—C11—H11C109.5
O1—C7—C4108.88 (13)H11B—C11—H11C109.5
O1—C7—C9110.69 (13)C8—N1—C5111.82 (14)
C4—C7—C9114.88 (14)C8—N1—H1A123.8
O1—C7—C8107.31 (13)C5—N1—H1A124.4
C4—C7—C8101.41 (13)C7—O1—H1109.5
C6—C1—C2—C31.6 (3)C3—C4—C7—C8174.9 (2)
Cl1—C1—C2—C3176.77 (18)C5—C4—C7—C83.61 (17)
C1—C2—C3—C40.1 (3)O1—C7—C8—O266.2 (2)
C2—C3—C4—C51.8 (3)C4—C7—C8—O2179.70 (16)
C2—C3—C4—C7179.90 (19)C9—C7—C8—O256.2 (2)
C3—C4—C5—C62.3 (3)O1—C7—C8—N1108.97 (15)
C7—C4—C5—C6178.99 (16)C4—C7—C8—N15.15 (17)
C3—C4—C5—N1177.66 (17)C9—C7—C8—N1128.68 (15)
C7—C4—C5—N11.02 (19)O1—C7—C9—C10178.81 (14)
C4—C5—C6—C10.9 (3)C4—C7—C9—C1057.4 (2)
N1—C5—C6—C1179.11 (18)C8—C7—C9—C1058.38 (19)
C2—C1—C6—C51.1 (3)C7—C9—C10—O316.1 (3)
Cl1—C1—C6—C5177.31 (14)C7—C9—C10—C11165.21 (19)
C3—C4—C7—O172.2 (2)O2—C8—N1—C5179.94 (17)
C5—C4—C7—O1109.33 (15)C7—C8—N1—C55.0 (2)
C3—C4—C7—C952.6 (3)C6—C5—N1—C8177.40 (17)
C5—C4—C7—C9125.91 (16)C4—C5—N1—C82.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.962.7510 (18)162
N1—H1A···O2ii0.852.192.9776 (19)154
C11—H11C···O3iii0.962.583.235 (3)126
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z+1; (iii) x+1/2, y+3/2, z+1.
 

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