Diethyl 2,2′-[({2-chloro-5-[(2-ethoxy-2-oxoethyl)(2-methylindolin-1-yl)carbamoyl]phenyl}sulfonyl)azanediyl]diacetate

The majority of the title molecule is disordered over two closely spaced locations; the conformation is approximately U-shaped. In the crystal, chains of molecules extending along the a-axis direction are formed by C—H⋯O and C—H⋯Cl hydrogen bonds and are connected into a corrugated layer structure parallel to the ab plane by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions.

The majority of the title molecule, C 28 H 34 ClN 3 O 9 S, is disordered over two closely spaced sets of sites; the site occupancy of the major component = 0.542 (3).The conformation of each component is approximately U-shaped with the chlorobenzene ring forming the base and the indolinyl and sulfamoyl groups the sides; an intramolecular C-H� � �Cl hydrogen bond possibly contributes to the stabilization of the conformation.In the crystal, a corrugated layer structure parallel to the ab plane is formed by C-H� � �O and C-H� � �Cl hydrogen bonds together with C-H� � ��(ring) interactions.

Structure description
Indapamide, is a dihydro-indole-based thiazide-like diuretic used to manage heart failure and treat hypertension.Various activities are associated with indole derivatives, including antiviral (Kadam & Wilson, 2016).As a continuation of our work in this area (e.g.Missioui et al., 2022), the title compound was synthesized and its crystal structure is reported here (Fig. 1) The molecule adopts an approximate U-shaped conformation (Fig. 1) with the chlorophenyl ring forming the base and the indolinyl and sulfamoyl groups the sides.The intramolecular C24-H24A� � �Cl1 hydrogen bond (Table 1) may help to stabilize this conformation.A puckering analysis (Cremer & Pople, 1975) of the two components of the five-membered ring gave the parameters Q(2) = 0.247 (8) A ˚and '(2) = 327 (2) � for the major component and Q(2) = 0.399 (9) A ˚and '(2) = 329.6 (16) � for the other.The dihedral angle between the mean planes of the C1-C6 and C15-C20 rings is 86.2 (4) � while that between the two disordered components of the C1-C6 ring is 3.8 (5) � and that between the two disordered components of the C15-C20 ring is 5.68 (6) � .
Cg4 is the centroid of the major orientation of the C15-C20 benzene ring.

Figure 2
View of a portion of one chain seen along the b-axis direction with intermolecular C-H� � �O and C-H� � �Cl hydrogen bonds depicted, respectively, by black and green dashed lines.Non-interacting hydrogen atoms are omitted.

Figure 3
Packing viewed along the c-axis direction with hydrogen bonds depicted as in Fig. 2. C-H� � ��(ring) interactions are depicted by light-purple dashed lines and non-interacting hydrogen atoms are omitted.

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids.
(10 mL), to which was added ethyl 2-bromoacetate (0.69 g, 4.5 mmol).Under reflux, the reaction was stirred for 3 h at 80 � C. When the starting reagents had reacted completely, distilled water (100 ml) was added.The product precipitated in solid form, was filtered, dried and recrystallized from ethanol solution to afford colorless blocks.

Refinement
Crystal data, data collection and structure refinement details are summarized in

Special details
Experimental.The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, collected at phi = 0.00, 90.00 and 180.00 deg.and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00and 210.00 deg.The scan time was 25 sec/frame.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 F 2 against ALL reflections.The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 .The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement.R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -1.00 Å).All were included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms.The ethyl 4chlorobenzyl-N-(2-methylindolin-1-yl)glycinate portion of the molecule is disordered over two partially resolved sites in a 0.542 (3):0.458(3) ratio.Also, the C23-C24 ethyl group is disordered over two sites in a 0.526 (12):0.474(12) ratio.The two components of each disorder were refined with restraints that their geometries be comparable.

Table 2
Experimental details.