1-(2,6-Dichlorophenyl)indolin-2-one
01 Mar 2009-Acta Crystallographica Section E-structure Reports Online (International Union of Crystallography)-Vol. 65, Iss: 3
TL;DR: In the molecule of the title compound, C14H9Cl2NO, the planar indole ring system is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring and a weak C—H⋯O hydrogen bonds link the molecules.
Abstract: In the molecule of the title compound, C14H9Cl2NO, the planar indole ring system [with a maximum deviation of 0.020 (2) A for the N atom] is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules. A weak C—H⋯π interaction may further stabilize the structure.
Citations
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TL;DR: Three 1-phenylindolin-2-one derivatives have been synthesized and their structures determined and density functional theory (DFT) calculations show that the molecular dipole moment gradually decreases in the order (I) > (II)> (III).
Abstract: Three 1-phenylindolin-2-one derivatives, namely 1-phenylindolin-2-one, C14H11NO, (I), 5-bromo-1-phenylindolin-2-one, C14H10BrNO, (II), and 5-iodo-1-phenylindolin-2-one, C14H10INO, (III), have been synthesized and their structures determined. Compounds (I) and (II) crystallized in the centrosymmetric space groups Pbca and P21/c, respectively, while compound (III) crystallized in the polar space group Aea2. Density functional theory (DFT) calculations show that the molecular dipole moment gradually decreases in the order (I) > (II) > (III). The relatively smaller dipole moment of (III) and the larger non-electrostatic intermolecular interactions may be the main reasons for the noncentrosymmetric and polar structure of (III).
4 citations
Cites background from "1-(2,6-Dichlorophenyl)indolin-2-o..."
...A larger angle of 72.2 (1) was found in 1-(2,6-dichlorophenyl)indolin-2-one (Hanif et al., 2009)....
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TL;DR: In this article, an effective and straightforward synthesis of 3-seleno functionalized indolinone (5) involving Vilsmeier reagent is presented, and a procedure to achieve lactamization of diclofenac with excellent yields by using hydrides is also ascertained.
Abstract: An effective and straightforward synthesis of 3-seleno functionalized indolinone (5) involving Vilsmeier reagent is presented. Likewise, a procedure to achieve lactamization of diclofenac with excellent yields by using hydrides is also ascertained. Compound 5 exhibited impressive growth inhibition in most of the cell lines in an NCI-60 panel, particularly towards resistant breast cancer cells.
1 citations
TL;DR: Density functional theory (DFT) calculations revealed a low oscillation barrier of the phenyl ring of molecule A and the phase transition from the P21/c structure to the P-1 structure can be interpreted in terms of the freezing out of the two conformations at low temperature.
Abstract: Three 1-phenylindolin-2-one derivatives, namely 6-chloro-1-phenylindolin-2-one (A), 4-chloro-1-phenylindolin-2-one (B) and 1-(3-chlorophenyl)indolin-2-one (C), all C14H10ClNO, have been synthesized and the structures of these compounds at room temperature (ART, BRT and CRT) and low temperature (ALT, BLT and CLT) have been determined. Crystal A at 295 K (ART) crystallized in the monoclinic space group P21/c and the phenyl ring of the unique molecule exhibits disorder over two positions. At low temperature, the disorder disappeared and crystal A at 90 K (ALT) crystallized in the triclinic space group P\overline{1} with a doubled unit-cell volume and four molecules in the asymmetric unit. Density functional theory (DFT) calculations revealed a low oscillation barrier (0.24 kcal mol−1) of the phenyl ring of molecule A and the phase transition from the P21/c structure to the P\overline{1} structure can be interpreted in terms of the freezing out of the two conformations at low temperature. Crystal B retains space group P21/c in the temperature range from 100 to 297 K. A kind of obtuse-cell to acute-cell change can be recognized; if the unit cell of BLT at 100 K is set to be a standard obtuse cell [β = 90.341 (2)°] and the cell is kept untransformed in the course of temperature changing, the cell of BRT at 297 K was found to be acute [β = 89.288 (2)°]. The molecules in structure C are packed in layers, with C—H⋯O hydrogen bonds between neighbouring layers.
References
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TL;DR: This paper could serve as a general literature citation when one or more of the open-source SH ELX programs (and the Bruker AXS version SHELXTL) are employed in the course of a crystal-structure determination.
Abstract: An account is given of the development of the SHELX system of computer programs from SHELX-76 to the present day. In addition to identifying useful innovations that have come into general use through their implementation in SHELX, a critical analysis is presented of the less-successful features, missed opportunities and desirable improvements for future releases of the software. An attempt is made to understand how a program originally designed for photographic intensity data, punched cards and computers over 10000 times slower than an average modern personal computer has managed to survive for so long. SHELXL is the most widely used program for small-molecule refinement and SHELXS and SHELXD are often employed for structure solution despite the availability of objectively superior programs. SHELXL also finds a niche for the refinement of macromolecules against high-resolution or twinned data; SHELXPRO acts as an interface for macromolecular applications. SHELXC, SHELXD and SHELXE are proving useful for the experimental phasing of macromolecules, especially because they are fast and robust and so are often employed in pipelines for high-throughput phasing. This paper could serve as a general literature citation when one or more of the open-source SHELX programs (and the Bruker AXS version SHELXTL) are employed in the course of a crystal-structure determination.
81,116 citations
TL;DR: L Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known.
Abstract: Computer Program Abstracts The category Computer Program Abstracts provides a rapid means of communicating up-to-date information concerning both new programs or systems and significant updates to existing ones. Following normal submission, a Computer Program Abstract will be reviewed by one or two members of the IUCr Commission on Crystallographic Computing. It should not exceed 500 words in length and should follow the standard format given on page 189 of the June 1985 issue of the Journal [J. Appl. CrysL (1985). 18, 189190] and on the World Wide Web at http://www.iucr. ac. uk/journals/jac/software/. Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known. J. App/. CrysL (1997). 30, 565 ORTEP-3 for Windows a version of ORTEP-III with a Graphical User Interface (GUI)
19,468 citations
TL;DR: This paper reports on the current status of structure validation in chemical crystallography and describes the current state of research in this area.
Abstract: Automated structure validation was introduced in chemical crystallography about 12 years ago as a tool to assist practitioners with the exponential growth in crystal structure analyses. Validation has since evolved into an easy-to-use checkCIF/PLATON web-based IUCr service. The result of a crystal structure determination has to be supplied as a CIF-formatted computer-readable file. The checking software tests the data in the CIF for completeness, quality and consistency. In addition, the reported structure is checked for incomplete analysis, errors in the analysis and relevant issues to be verified. A validation report is generated in the form of a list of ALERTS on the issues to be corrected, checked or commented on. Structure validation has largely eliminated obvious problems with structure reports published in IUCr journals, such as refinement in a space group of too low symmetry. This paper reports on the current status of structure validation and possible future extensions.
13,163 citations
TL;DR: In this article, the behaviour of the Rogers's η parameter for enantiomorph-polarity estimation is examined theoretically and experimentally on simulated intensity data for seven well-assorted compounds.
Abstract: The behaviour of Rogers's η parameter for enantiomorph-polarity estimation is examined theoretically and experimentally on simulated intensity data for seven well-assorted compounds. An alternative parameter x, based on incoherent scattering from twin components related by a centre of symmetry, is also considered. It is found that both parameters are very well adapted to implementation in a least-squares program and converge well. The η parameter can give false and over-precise indications of chirality-polarity for structures which are nearly centrosymmetric, whereas the x parameter does not have this fault and converges more rapidly than η.
9,932 citations
"1-(2,6-Dichlorophenyl)indolin-2-o..." refers background in this paper
...Refinement on F2 Hydrogen site location: inferred from neighbouring sites Least-squares matrix: full H-atom parameters constrained R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.0681P] where P = (Fo2 + 2Fc2)/3 wR(F2) = 0.060 (Δ/σ)max 0.001 S = 1.06 Δρmax = 0.19 e Å−3 2328 reflections Δρmin = −0.16 e Å−3 163 parameters Extinction correction: none 1 restraint Absolute structure: Flack (1983), 705 Friedel pairs Primary atom site location: structure-invariant direct methods Flack parameter: −0.02 (4) Secondary atom site location: difference Fourier map...
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...…(Δ/σ)max 0.001 S = 1.06 Δρmax = 0.19 e Å−3 2328 reflections Δρmin = −0.16 e Å−3 163 parameters Extinction correction: none 1 restraint Absolute structure: Flack (1983), 705 Friedel pairs Primary atom site location: structure-invariant direct methods Flack parameter: −0.02 (4) Secondary atom…...
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...R[F 2 > 2 (F 2)] = 0.021 wR(F 2) = 0.060 S = 1.06 2328 reflections 163 parameters 1 restraint H-atom parameters constrained max = 0.19 e Å 3 min = 0.16 e Å 3 Absolute structure: Flack (1983), 705 Friedel pairs Flack parameter: 0.02 (4)...
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TL;DR: The average lengths of bonds involving the elements H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, and l in organic compounds are reported in this article.
Abstract: The average lengths of bonds involving the elements H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, and l in organic compounds are reported.
6,649 citations
"1-(2,6-Dichlorophenyl)indolin-2-o..." refers background in this paper
...1), the bond lengths (Allen et al., 1987) and angles are within normal ranges....
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