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
CCDC reference: 651481
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
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) Å3 | Block, colorless |
Z = 4 | 0.30 × 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 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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.96 | 2.7510 (18) | 162 |
N1—H1A···O2ii | 0.85 | 2.19 | 2.9776 (19) | 154 |
C11—H11C···O3iii | 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. |