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Three isatin derivatives, namely, 1-allyl-3-hy­droxy-3-(6-oxo­cyclo­hex-1-en-1-yl)indolin-2-one, C17H17NO3, 1-ethyl-3-hy­droxy-3-(6-oxo­cyclo­hex-1-en-1-yl)indolin-2-one, C16H17NO3, and 5-bromo-3-hy­droxy-1-methyl-3-(6-oxo­cyclo­hex-1-en-1-yl)indolin-2-one, C15H14BrNO3, were synthesized, crystallized by the slow-evaporation technique, characterized by 1H and 13C NMR spectroscopy, and analysed by the single-crystal X-ray diffraction (XRD) method. Quantum chemical parameters, such as the energy of the highest occupied mol­ecular orbital, energy of the lowest unoccupied mol­ecular orbital, energy gap, electronic energy, ionization potential, chemical potential, global hardness, global softness and electrophilicity index, were calculated. The druglikeness and bioactivity scores of the com­pounds were calculated. The activities of these isatin derivatives against bacterial strains, such as Eschericia coli, Proteus vulgaris, Shigella flexneri, Staphylococcus aureus and Micrococcus luteus, and the fungal strain Aspergillus niger, were determined using the well-diffusion assay method. Mol­ecular docking studies were carried out to predict the binding mode of the isatin com­pounds with the penicillin binding protein enzyme and to identify the inter­actions between the enzyme and the ligands under study.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621004940/ef3014sup1.cif
Contains datablocks I_shelx, II_shelx, III_shelx, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014I_shelxsup2.hkl
Contains datablock I_shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014II_shelxsup3.hkl
Contains datablock II_shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004940/ef3014III_shelxsup4.hkl
Contains datablock III_shelx

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014I_shelxsup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014II_shelxsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621004940/ef3014III_shelxsup7.cml
Supplementary material

CCDC references: 1828486; 1828014; 1828286

Computing details top

For all structures, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

3-Hydroxy-3-(6-oxocyclohex-1-en-1-yl)-1-(prop-2-en-1-yl)indol-2-one (I_shelx) top
Crystal data top
C17H17NO3F(000) = 600
Mr = 283.31Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.6750 (7) ÅCell parameters from 2006 reflections
b = 8.6138 (5) Åθ = 2.9–25.0°
c = 14.1504 (8) ŵ = 0.09 mm1
β = 90.075 (2)°T = 296 K
V = 1423.05 (14) Å3Block, colourless
Z = 40.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2006 reflections with I > 2σ(I)
ω and φ scanRint = 0.038
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 25.0°, θmin = 2.9°
Tmin = 0.547, Tmax = 0.746h = 1313
25650 measured reflectionsk = 1010
2492 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0497P)2 + 1.0412P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
2492 reflectionsΔρmax = 0.34 e Å3
200 parametersΔρmin = 0.35 e Å3
0 restraints
Special details top

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. IS1

Alert level G

PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report

The H atom on the O2 hydroxy group was fixed at the calculated position and refined using a riding model with respect to its parent atom, with Uiso(H) = 1.5Ueq(O).

The terminal carbon atom (C17)of the allyl group was disordered over two positions with an occupancy ratio of 77:23.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C170.4443 (3)0.3678 (5)0.1214 (3)0.0569 (13)0.774 (9)
H17A0.3832990.3363570.1589630.068*0.774 (9)
H17B0.4589600.3172570.0645660.068*0.774 (9)
C17'0.5389 (15)0.3786 (16)0.0988 (11)0.073 (5)0.226 (9)
H17C0.5996960.3169620.1187230.088*0.226 (9)
H17D0.5055720.3616130.0399530.088*0.226 (9)
O20.29807 (13)0.57697 (18)0.50335 (10)0.0396 (4)
H20.3337070.5288970.5438550.059*
O10.25038 (14)0.24387 (19)0.28918 (10)0.0433 (4)
O30.48480 (12)0.39949 (18)0.40727 (11)0.0410 (4)
N10.40062 (15)0.5493 (2)0.29226 (12)0.0350 (4)
C80.21765 (18)0.5725 (2)0.34877 (14)0.0324 (5)
C70.28373 (17)0.4819 (2)0.42217 (13)0.0295 (4)
C10.21858 (17)0.2127 (2)0.36904 (14)0.0316 (5)
C60.23232 (16)0.3253 (2)0.44683 (13)0.0300 (5)
C140.40240 (17)0.4671 (2)0.37351 (14)0.0308 (5)
C130.29131 (19)0.6134 (2)0.27556 (15)0.0349 (5)
C50.19747 (19)0.2887 (3)0.53363 (15)0.0398 (5)
H50.2044740.3636480.5805990.048*
C20.1618 (2)0.0607 (3)0.39103 (16)0.0464 (6)
H2A0.1911530.0182130.3485550.056*
H2B0.0801230.0702440.3797310.056*
C30.1811 (2)0.0089 (3)0.49190 (16)0.0461 (6)
H3A0.1359710.0834480.5043650.055*
H3B0.2611890.0172720.5007830.055*
C90.1052 (2)0.6184 (3)0.34597 (17)0.0425 (6)
H90.0547790.5904290.3938230.051*
C110.1425 (3)0.7494 (3)0.19900 (18)0.0556 (7)
H110.1160180.8101110.1492020.067*
C40.1478 (2)0.1349 (3)0.56037 (17)0.0470 (6)
H4A0.0649950.1431260.5623000.056*
H4B0.1741630.1069510.6231540.056*
C120.2561 (2)0.7025 (3)0.20011 (16)0.0473 (6)
H120.3062860.7300210.1519860.057*
C100.0683 (2)0.7082 (3)0.26962 (19)0.0530 (7)
H100.0076510.7404870.2666940.064*
C150.5000 (2)0.5719 (3)0.23170 (18)0.0519 (7)
H15A0.5683640.5523880.2688970.062*
H15B0.5020130.6798590.2123720.062*
C160.5051 (3)0.4749 (4)0.1465 (2)0.0753 (9)
H160.5642300.4992860.1051360.090*0.774 (9)
H16'0.4462380.5163680.1100730.090*0.226 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.052 (3)0.070 (3)0.049 (2)0.0023 (19)0.0018 (17)0.0017 (18)
C17'0.089 (13)0.060 (9)0.071 (9)0.001 (7)0.040 (8)0.012 (7)
O20.0435 (9)0.0422 (9)0.0332 (8)0.0048 (7)0.0038 (6)0.0122 (6)
O10.0539 (10)0.0439 (9)0.0323 (8)0.0099 (7)0.0047 (7)0.0038 (7)
O30.0318 (8)0.0457 (9)0.0456 (9)0.0038 (7)0.0053 (7)0.0086 (7)
N10.0324 (10)0.0364 (10)0.0363 (9)0.0081 (8)0.0043 (7)0.0011 (8)
C80.0362 (11)0.0270 (10)0.0340 (11)0.0015 (9)0.0025 (9)0.0062 (8)
C70.0308 (10)0.0298 (10)0.0278 (10)0.0005 (8)0.0006 (8)0.0056 (8)
C10.0279 (11)0.0351 (11)0.0318 (11)0.0024 (8)0.0022 (8)0.0003 (9)
C60.0246 (10)0.0347 (11)0.0306 (10)0.0018 (8)0.0003 (8)0.0004 (8)
C140.0306 (11)0.0294 (10)0.0324 (10)0.0046 (8)0.0031 (8)0.0090 (8)
C130.0413 (12)0.0265 (10)0.0368 (11)0.0044 (9)0.0046 (9)0.0034 (9)
C50.0409 (13)0.0444 (13)0.0341 (11)0.0010 (10)0.0053 (9)0.0015 (10)
C20.0543 (15)0.0410 (13)0.0440 (13)0.0158 (11)0.0064 (11)0.0028 (10)
C30.0512 (14)0.0400 (13)0.0471 (13)0.0094 (11)0.0014 (11)0.0092 (11)
C90.0378 (12)0.0436 (13)0.0460 (13)0.0064 (10)0.0054 (10)0.0104 (10)
C110.086 (2)0.0381 (13)0.0432 (13)0.0128 (13)0.0223 (14)0.0030 (11)
C40.0470 (14)0.0533 (15)0.0407 (12)0.0036 (11)0.0091 (10)0.0093 (11)
C120.0692 (17)0.0344 (12)0.0383 (12)0.0035 (11)0.0054 (11)0.0024 (10)
C100.0520 (15)0.0499 (15)0.0571 (15)0.0181 (12)0.0228 (12)0.0150 (12)
C150.0468 (14)0.0571 (16)0.0519 (15)0.0126 (12)0.0172 (11)0.0011 (12)
C160.089 (2)0.084 (2)0.0539 (17)0.001 (2)0.0196 (16)0.0069 (17)
Geometric parameters (Å, º) top
C17—C161.217 (5)C5—C41.495 (3)
C17—H17A0.9300C5—H50.9300
C17—H17B0.9300C2—C31.512 (3)
C17'—C161.141 (13)C2—H2A0.9700
C17'—H17C0.9300C2—H2B0.9700
C17'—H17D0.9300C3—C41.506 (3)
O2—C71.420 (2)C3—H3A0.9700
O2—H20.8200C3—H3B0.9700
O1—C11.220 (2)C9—C101.397 (3)
O3—C141.221 (3)C9—H90.9300
N1—C141.350 (3)C11—C101.370 (4)
N1—C131.410 (3)C11—C121.387 (4)
N1—C151.456 (3)C11—H110.9300
C8—C91.371 (3)C4—H4A0.9700
C8—C131.392 (3)C4—H4B0.9700
C8—C71.510 (3)C12—H120.9300
C7—C61.517 (3)C10—H100.9300
C7—C141.553 (3)C15—C161.467 (4)
C1—C61.476 (3)C15—H15A0.9700
C1—C21.501 (3)C15—H15B0.9700
C6—C51.332 (3)C16—H160.9300
C13—C121.378 (3)C16—H16'0.9300
C16—C17—H17A120.0C3—C2—H2B109.0
C16—C17—H17B120.0H2A—C2—H2B107.8
H17A—C17—H17B120.0C4—C3—C2110.9 (2)
C16—C17'—H17C120.0C4—C3—H3A109.5
C16—C17'—H17D120.0C2—C3—H3A109.5
H17C—C17'—H17D120.0C4—C3—H3B109.5
C7—O2—H2109.5C2—C3—H3B109.5
C14—N1—C13111.15 (17)H3A—C3—H3B108.1
C14—N1—C15124.0 (2)C8—C9—C10118.5 (2)
C13—N1—C15124.81 (19)C8—C9—H9120.8
C9—C8—C13119.8 (2)C10—C9—H9120.8
C9—C8—C7131.1 (2)C10—C11—C12121.5 (2)
C13—C8—C7109.08 (18)C10—C11—H11119.3
O2—C7—C8108.55 (16)C12—C11—H11119.3
O2—C7—C6111.89 (16)C5—C4—C3112.05 (18)
C8—C7—C6114.55 (16)C5—C4—H4A109.2
O2—C7—C14107.55 (15)C3—C4—H4A109.2
C8—C7—C14101.10 (16)C5—C4—H4B109.2
C6—C7—C14112.49 (16)C3—C4—H4B109.2
O1—C1—C6120.88 (19)H4A—C4—H4B107.9
O1—C1—C2121.29 (19)C13—C12—C11117.1 (2)
C6—C1—C2117.81 (18)C13—C12—H12121.4
C5—C6—C1119.9 (2)C11—C12—H12121.4
C5—C6—C7122.94 (19)C11—C10—C9120.8 (2)
C1—C6—C7117.10 (16)C11—C10—H10119.6
O3—C14—N1126.47 (19)C9—C10—H10119.6
O3—C14—C7124.63 (18)N1—C15—C16116.1 (2)
N1—C14—C7108.77 (17)N1—C15—H15A108.3
C12—C13—C8122.2 (2)C16—C15—H15A108.3
C12—C13—N1128.1 (2)N1—C15—H15B108.3
C8—C13—N1109.64 (18)C16—C15—H15B108.3
C6—C5—C4124.2 (2)H15A—C15—H15B107.4
C6—C5—H5117.9C17'—C16—C15156.2 (10)
C4—C5—H5117.9C17—C16—C15130.4 (3)
C1—C2—C3112.82 (18)C17—C16—H16114.8
C1—C2—H2A109.0C15—C16—H16114.8
C3—C2—H2A109.0C17'—C16—H16'101.9
C1—C2—H2B109.0C15—C16—H16'101.9
C9—C8—C7—O270.4 (3)C9—C8—C13—C121.5 (3)
C13—C8—C7—O2108.18 (18)C7—C8—C13—C12177.25 (19)
C9—C8—C7—C655.5 (3)C9—C8—C13—N1178.09 (18)
C13—C8—C7—C6125.98 (18)C7—C8—C13—N13.2 (2)
C9—C8—C7—C14176.7 (2)C14—N1—C13—C12179.4 (2)
C13—C8—C7—C144.8 (2)C15—N1—C13—C122.3 (3)
O1—C1—C6—C5179.7 (2)C14—N1—C13—C80.2 (2)
C2—C1—C6—C51.7 (3)C15—N1—C13—C8178.17 (19)
O1—C1—C6—C71.9 (3)C1—C6—C5—C42.5 (3)
C2—C1—C6—C7176.61 (18)C7—C6—C5—C4179.2 (2)
O2—C7—C6—C54.7 (3)O1—C1—C2—C3151.6 (2)
C8—C7—C6—C5119.3 (2)C6—C1—C2—C329.9 (3)
C14—C7—C6—C5125.9 (2)C1—C2—C3—C452.9 (3)
O2—C7—C6—C1176.97 (16)C13—C8—C9—C101.1 (3)
C8—C7—C6—C158.9 (2)C7—C8—C9—C10177.3 (2)
C14—C7—C6—C155.8 (2)C6—C5—C4—C321.6 (3)
C13—N1—C14—O3179.25 (19)C2—C3—C4—C548.2 (3)
C15—N1—C14—O30.9 (3)C8—C13—C12—C110.7 (3)
C13—N1—C14—C73.4 (2)N1—C13—C12—C11178.7 (2)
C15—N1—C14—C7175.00 (19)C10—C11—C12—C130.3 (4)
O2—C7—C14—O367.2 (2)C12—C11—C10—C90.6 (4)
C8—C7—C14—O3179.13 (19)C8—C9—C10—C110.1 (4)
C6—C7—C14—O356.5 (3)C14—N1—C15—C16101.9 (3)
O2—C7—C14—N1108.81 (18)C13—N1—C15—C1679.9 (3)
C8—C7—C14—N14.9 (2)N1—C15—C16—C17'110.1 (19)
C6—C7—C14—N1127.54 (17)N1—C15—C16—C177.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.822.312.839 (2)123
C15—H15B···O3ii0.972.543.444 (3)155
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1/2, z+1/2.
1-Ethyl-3-hydroxy-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one (II_shelx) top
Crystal data top
C16H17NO3F(000) = 576
Mr = 271.30Dx = 1.248 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.9227 (6) ÅCell parameters from 1892 reflections
b = 12.8741 (6) Åθ = 2.3–26.3°
c = 12.5994 (8) ŵ = 0.09 mm1
β = 93.897 (3)°T = 296 K
V = 1443.97 (15) Å3Block, colourless
Z = 40.35 × 0.30 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
1892 reflections with I > 2σ(I)
ω and φ scanRint = 0.036
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 26.0°, θmin = 2.3°
Tmin = 0.716, Tmax = 0.746h = 119
19991 measured reflectionsk = 1515
2837 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0455P)2 + 0.4767P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2837 reflectionsΔρmax = 0.16 e Å3
210 parametersΔρmin = 0.15 e Å3
77 restraints
Special details top

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. IS2

Alert level G

1. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 Note

Atoms C2, C3, C4 of cyclohexenone moiety are disordered over two positions. The disordered positions were located from difference electron density peaks and refined with a target C-C distance of 1.52 Å using DFIX instruction.

2. PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ··· 6 Report

The thermal parameters of atoms in the disordered group are restrained with an effective standard deviation of 0.02 Å2 to have the same Uij components.

3. PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report

The hydrogen on hydroxy group was fixed at calculated position and refined as a riding model with respect to its parent atom with Uiso(H) = 1.5Ueq(O).

4. PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report

The atoms C2, C3, C4 of cyclohexenone moiety is disordered over two positions. The disordered positions were located from difference electron density peaks and refined with a target C—C distance of 1.52 Å using DFIX instruction.

5. PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 2 Report

The components of the anisotropic displacement parameters in the direction of the bond of disordered atoms are restrained to be equal within an effective standard deviation of 0.01 using DELU instruction.

6. PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report

The atoms (C2, C3, C4) in the disordered group are restrained with an effective standard deviation of 0.02 Å2 to have the same Uij components using the SIMU instruction.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.7567 (2)0.33711 (16)0.19077 (15)0.0503 (5)
C20.9239 (5)0.3497 (6)0.2123 (7)0.083 (2)0.720 (9)
H2A0.97450.28800.18860.100*0.720 (9)
H2B0.94740.35710.28820.100*0.720 (9)
C30.9802 (5)0.4439 (3)0.1552 (6)0.0914 (16)0.720 (9)
H3A0.95870.43630.07900.110*0.720 (9)
H3B1.08810.45030.16900.110*0.720 (9)
C40.9024 (6)0.5410 (6)0.1944 (10)0.088 (2)0.720 (9)
H4A0.93900.55590.26710.105*0.720 (9)
H4B0.92560.59990.15050.105*0.720 (9)
C2'0.9248 (12)0.3438 (17)0.181 (2)0.084 (4)0.280 (9)
H2'10.97310.28300.21280.101*0.280 (9)
H2'20.94480.34460.10580.101*0.280 (9)
C3'0.9899 (11)0.4406 (8)0.2338 (15)0.086 (3)0.280 (9)
H3'11.09620.44590.22300.103*0.280 (9)
H3'20.97760.43820.30970.103*0.280 (9)
C4'0.9059 (10)0.5334 (16)0.184 (2)0.079 (4)0.280 (9)
H4'10.94080.59620.22050.094*0.280 (9)
H4'20.92900.53940.11020.094*0.280 (9)
C50.7371 (2)0.52491 (16)0.18965 (16)0.0573 (5)
H50.67670.58380.18860.069*
C60.66896 (19)0.43340 (13)0.18680 (13)0.0389 (4)
C70.49995 (19)0.42239 (12)0.17933 (13)0.0373 (4)
C80.43427 (19)0.37039 (13)0.27260 (14)0.0413 (4)
C90.4432 (2)0.39694 (16)0.37818 (16)0.0556 (5)
H90.50060.45340.40270.067*
C100.3646 (3)0.33750 (19)0.44785 (18)0.0682 (6)
H100.36790.35470.51970.082*
C110.2823 (3)0.25373 (19)0.41093 (19)0.0698 (7)
H110.23120.21440.45880.084*
C120.2727 (2)0.22584 (16)0.30507 (18)0.0594 (6)
H120.21710.16840.28090.071*
C130.3485 (2)0.28613 (14)0.23678 (15)0.0445 (5)
C140.4437 (2)0.34990 (13)0.08747 (15)0.0416 (4)
C150.2720 (3)0.20116 (17)0.05734 (19)0.0673 (6)
H15A0.24400.23330.01080.081*
H15B0.18020.18170.08940.081*
C160.3601 (4)0.1063 (2)0.0393 (3)0.1041 (10)
H16A0.30130.05960.00600.156*
H16B0.45010.12460.00600.156*
H16C0.38620.07300.10620.156*
N10.35269 (17)0.27687 (11)0.12560 (13)0.0478 (4)
O10.69642 (17)0.25271 (11)0.18388 (13)0.0672 (4)
O20.42546 (14)0.51902 (9)0.16291 (10)0.0500 (4)
H20.45450.54700.10950.075*
O30.46968 (16)0.35971 (10)0.00586 (10)0.0545 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0423 (12)0.0531 (12)0.0557 (12)0.0060 (10)0.0062 (9)0.0013 (9)
C20.042 (3)0.092 (4)0.114 (5)0.018 (3)0.004 (2)0.020 (3)
C30.0365 (19)0.119 (3)0.120 (4)0.015 (2)0.014 (2)0.021 (3)
C40.056 (4)0.083 (4)0.124 (5)0.019 (3)0.006 (4)0.020 (4)
C2'0.041 (6)0.095 (7)0.115 (10)0.010 (6)0.002 (6)0.046 (7)
C3'0.038 (4)0.095 (6)0.122 (7)0.001 (4)0.007 (5)0.026 (6)
C4'0.040 (8)0.090 (7)0.105 (9)0.032 (7)0.001 (7)0.006 (8)
C50.0492 (13)0.0518 (12)0.0709 (14)0.0060 (10)0.0031 (10)0.0075 (10)
C60.0371 (10)0.0406 (10)0.0397 (9)0.0001 (8)0.0069 (7)0.0012 (7)
C70.0355 (10)0.0321 (9)0.0453 (10)0.0043 (7)0.0089 (7)0.0051 (7)
C80.0355 (10)0.0419 (10)0.0477 (11)0.0061 (8)0.0112 (8)0.0071 (8)
C90.0560 (13)0.0595 (12)0.0525 (12)0.0012 (10)0.0129 (10)0.0027 (9)
C100.0683 (16)0.0865 (17)0.0523 (12)0.0039 (14)0.0222 (11)0.0136 (12)
C110.0559 (14)0.0845 (17)0.0720 (16)0.0013 (13)0.0255 (12)0.0310 (13)
C120.0425 (12)0.0590 (13)0.0779 (16)0.0075 (10)0.0119 (10)0.0185 (11)
C130.0311 (10)0.0468 (11)0.0563 (12)0.0021 (8)0.0080 (8)0.0106 (9)
C140.0362 (10)0.0399 (10)0.0490 (11)0.0050 (8)0.0044 (8)0.0067 (8)
C150.0561 (14)0.0667 (14)0.0781 (15)0.0177 (11)0.0031 (11)0.0031 (12)
C160.111 (2)0.0780 (18)0.120 (2)0.0010 (17)0.0182 (19)0.0309 (17)
N10.0410 (9)0.0469 (9)0.0556 (10)0.0095 (7)0.0028 (7)0.0026 (7)
O10.0585 (10)0.0445 (8)0.0994 (12)0.0102 (7)0.0112 (8)0.0072 (7)
O20.0493 (8)0.0395 (7)0.0630 (9)0.0117 (6)0.0170 (6)0.0098 (6)
O30.0646 (9)0.0544 (8)0.0447 (8)0.0034 (7)0.0062 (7)0.0047 (6)
Geometric parameters (Å, º) top
C1—O11.213 (2)C7—O21.4190 (19)
C1—C61.465 (3)C7—C81.505 (2)
C1—C21.507 (5)C7—C141.544 (2)
C1—C2'1.516 (10)C8—C91.370 (3)
C2—C31.514 (7)C8—C131.385 (3)
C2—H2A0.9700C9—C101.390 (3)
C2—H2B0.9700C9—H90.9300
C3—C41.528 (8)C10—C111.368 (3)
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700C11—C121.378 (3)
C4—C51.486 (6)C11—H110.9300
C4—H4A0.9700C12—C131.371 (3)
C4—H4B0.9700C12—H120.9300
C2'—C3'1.512 (10)C13—N11.409 (2)
C2'—H2'10.9700C14—O31.220 (2)
C2'—H2'20.9700C14—N11.352 (2)
C3'—C4'1.523 (10)C15—N11.457 (3)
C3'—H3'10.9700C15—C161.478 (3)
C3'—H3'20.9700C15—H15A0.9700
C4'—C51.516 (9)C15—H15B0.9700
C4'—H4'10.9700C16—H16A0.9600
C4'—H4'20.9700C16—H16B0.9600
C5—C61.325 (3)C16—H16C0.9600
C5—H50.9300O2—H20.8200
C6—C71.511 (2)
O1—C1—C6121.48 (17)C5—C6—C7122.64 (16)
O1—C1—C2122.5 (4)C1—C6—C7116.83 (15)
C6—C1—C2115.8 (3)O2—C7—C8107.48 (13)
O1—C1—C2'118.8 (8)O2—C7—C6112.48 (13)
C6—C1—C2'118.5 (9)C8—C7—C6115.65 (14)
C1—C2—C3110.9 (5)O2—C7—C14107.18 (13)
C1—C2—H2A109.5C8—C7—C14101.09 (14)
C3—C2—H2A109.5C6—C7—C14112.06 (13)
C1—C2—H2B109.5C9—C8—C13120.38 (17)
C3—C2—H2B109.5C9—C8—C7130.30 (17)
H2A—C2—H2B108.0C13—C8—C7109.25 (15)
C2—C3—C4109.2 (7)C8—C9—C10118.5 (2)
C2—C3—H3A109.8C8—C9—H9120.7
C4—C3—H3A109.8C10—C9—H9120.7
C2—C3—H3B109.8C11—C10—C9120.1 (2)
C4—C3—H3B109.8C11—C10—H10119.9
H3A—C3—H3B108.3C9—C10—H10119.9
C5—C4—C3110.2 (5)C10—C11—C12122.05 (19)
C5—C4—H4A109.6C10—C11—H11119.0
C3—C4—H4A109.6C12—C11—H11119.0
C5—C4—H4B109.6C13—C12—C11117.3 (2)
C3—C4—H4B109.6C13—C12—H12121.3
H4A—C4—H4B108.1C11—C12—H12121.3
C3'—C2'—C1111.2 (10)C12—C13—C8121.61 (19)
C3'—C2'—H2'1109.4C12—C13—N1128.59 (18)
C1—C2'—H2'1109.4C8—C13—N1109.79 (15)
C3'—C2'—H2'2109.4O3—C14—N1124.92 (17)
C1—C2'—H2'2109.4O3—C14—C7125.90 (16)
H2'1—C2'—H2'2108.0N1—C14—C7109.06 (15)
C2'—C3'—C4'107.5 (19)N1—C15—C16113.4 (2)
C2'—C3'—H3'1110.2N1—C15—H15A108.9
C4'—C3'—H3'1110.2C16—C15—H15A108.9
C2'—C3'—H3'2110.2N1—C15—H15B108.9
C4'—C3'—H3'2110.2C16—C15—H15B108.9
H3'1—C3'—H3'2108.5H15A—C15—H15B107.7
C5—C4'—C3'112.7 (10)C15—C16—H16A109.5
C5—C4'—H4'1109.0C15—C16—H16B109.5
C3'—C4'—H4'1109.0H16A—C16—H16B109.5
C5—C4'—H4'2109.0C15—C16—H16C109.5
C3'—C4'—H4'2109.0H16A—C16—H16C109.5
H4'1—C4'—H4'2107.8H16B—C16—H16C109.5
C6—C5—C4125.3 (3)C14—N1—C13110.60 (15)
C6—C5—C4'121.2 (8)C14—N1—C15122.69 (17)
C6—C5—H5117.4C13—N1—C15126.72 (16)
C4—C5—H5117.4C7—O2—H2109.5
C5—C6—C1120.52 (17)
O1—C1—C2—C3145.9 (5)C6—C7—C8—C13124.16 (16)
C6—C1—C2—C338.7 (7)C14—C7—C8—C132.91 (17)
C1—C2—C3—C460.3 (9)C13—C8—C9—C100.0 (3)
C2—C3—C4—C550.3 (10)C7—C8—C9—C10176.75 (18)
O1—C1—C2'—C3'156.7 (15)C8—C9—C10—C110.9 (3)
C6—C1—C2'—C3'36 (2)C9—C10—C11—C120.7 (4)
C1—C2'—C3'—C4'57 (3)C10—C11—C12—C130.5 (3)
C2'—C3'—C4'—C555 (3)C11—C12—C13—C81.5 (3)
C3—C4—C5—C620.8 (10)C11—C12—C13—N1177.50 (19)
C3'—C4'—C5—C631 (3)C9—C8—C13—C121.2 (3)
C4—C5—C6—C11.4 (6)C7—C8—C13—C12178.59 (16)
C4'—C5—C6—C17.2 (13)C9—C8—C13—N1177.89 (17)
C4—C5—C6—C7178.5 (6)C7—C8—C13—N10.55 (19)
C4'—C5—C6—C7172.7 (13)O2—C7—C14—O368.3 (2)
O1—C1—C6—C5176.95 (19)C8—C7—C14—O3179.34 (17)
C2—C1—C6—C57.6 (4)C6—C7—C14—O355.6 (2)
C2'—C1—C6—C59.6 (11)O2—C7—C14—N1107.96 (15)
O1—C1—C6—C73.0 (3)C8—C7—C14—N14.44 (17)
C2—C1—C6—C7172.5 (4)C6—C7—C14—N1128.19 (15)
C2'—C1—C6—C7170.4 (10)O3—C14—N1—C13179.29 (17)
C5—C6—C7—O27.2 (2)C7—C14—N1—C134.45 (19)
C1—C6—C7—O2172.80 (14)O3—C14—N1—C151.0 (3)
C5—C6—C7—C8116.86 (19)C7—C14—N1—C15175.25 (16)
C1—C6—C7—C863.2 (2)C12—C13—N1—C14178.41 (18)
C5—C6—C7—C14127.99 (18)C8—C13—N1—C142.5 (2)
C1—C6—C7—C1452.0 (2)C12—C13—N1—C151.9 (3)
O2—C7—C8—C967.7 (2)C8—C13—N1—C15177.15 (18)
C6—C7—C8—C958.8 (2)C16—C15—N1—C1487.6 (3)
C14—C7—C8—C9179.91 (19)C16—C15—N1—C1392.8 (3)
O2—C7—C8—C13109.26 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.932.7350 (18)167
C11—H11···O3ii0.932.593.378 (3)143
C12—H12···O2iii0.932.443.237 (2)144
Symmetry codes: (i) x+1, y+1, z; (ii) x1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2.
5-Bromo-3-hydroxy-1-methyl-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one (III_shelx) top
Crystal data top
C15H14BrNO3Dx = 1.580 Mg m3
Mr = 336.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2203 reflections
a = 7.8960 (3) Åθ = 3.3–25.0°
b = 19.6458 (8) ŵ = 2.92 mm1
c = 9.1088 (3) ÅT = 296 K
V = 1412.99 (9) Å3Block, colourless
Z = 40.20 × 0.20 × 0.15 mm
F(000) = 680
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2203 reflections with I > 2σ(I)
ω and φ scanRint = 0.035
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 25.0°, θmin = 3.3°
Tmin = 0.550, Tmax = 0.746h = 99
25065 measured reflectionsk = 2323
2365 independent reflectionsl = 1010
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0653P)2 + 0.434P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.31 e Å3
2365 reflectionsΔρmin = 0.78 e Å3
182 parametersAbsolute structure: Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.027 (4)
Primary atom site location: structure-invariant direct methods
Special details top

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. IS3

Alert level C

1. PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 1 Check

This low-angle reflection is affected by the beam stop. Hence its I(obs) is much smaller than I(calc)

2. PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 1 Check

This low angle reflection is affected by the beam stop. Hence its I(obs) is much smaller than I(calc)

Alert level G

3. PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ············.. 1 Report

The hydroxy H atom was fixed at the calculated position and refined using a riding model with respect to its parent atom, with Uiso(H) = 1.5Ueq(O)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.31672 (8)0.32391 (3)0.11497 (10)0.0624 (3)
O10.2107 (6)0.3645 (2)0.7638 (7)0.0660 (13)
O30.6023 (4)0.43342 (18)0.8846 (4)0.0376 (7)
O20.5834 (3)0.49520 (14)0.5940 (4)0.0314 (7)
H20.5494530.5112270.5162150.047*
N10.6094 (5)0.3447 (2)0.7237 (5)0.0364 (9)
C30.0437 (9)0.5236 (5)0.8846 (10)0.083 (3)
H3A0.1116230.5205760.9731260.100*
H3B0.0661270.5417670.9116060.100*
C40.1279 (8)0.5717 (4)0.7790 (8)0.0615 (18)
H4A0.0466560.5854470.7048340.074*
H4B0.1637720.6121340.8314520.074*
C50.2784 (6)0.5400 (3)0.7055 (6)0.0365 (11)
H50.3573280.5685680.6614990.044*
C60.3050 (5)0.4732 (2)0.6997 (5)0.0256 (9)
C70.4709 (5)0.44369 (18)0.6413 (4)0.0231 (9)
C80.4589 (5)0.3868 (2)0.5291 (5)0.0278 (9)
C90.3891 (6)0.3861 (2)0.3893 (5)0.0316 (9)
H90.3319080.4235820.3516700.038*
C100.4086 (7)0.3264 (3)0.3078 (6)0.0397 (12)
C110.4935 (8)0.2698 (3)0.3627 (7)0.0498 (14)
H110.5032460.2306940.3057290.060*
C20.0215 (9)0.4557 (5)0.8241 (10)0.079 (2)
H2A0.0631380.4575600.7470370.095*
H2B0.0209630.4259030.9005920.095*
C10.1816 (6)0.4257 (3)0.7623 (7)0.0423 (12)
C140.5661 (5)0.4075 (2)0.7672 (5)0.0291 (9)
C130.5457 (6)0.3304 (2)0.5830 (6)0.0340 (12)
C120.5632 (7)0.2715 (2)0.5013 (7)0.0460 (13)
H120.6205110.2339940.5389610.055*
C150.7016 (8)0.2968 (3)0.8157 (9)0.0565 (16)
H15A0.7416540.3197120.9020750.085*
H15B0.7961800.2788500.7620070.085*
H15C0.6277310.2602160.8437540.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0783 (4)0.0760 (4)0.0329 (4)0.0279 (3)0.0028 (3)0.0196 (3)
O10.069 (3)0.047 (2)0.081 (4)0.0148 (19)0.030 (2)0.005 (2)
O30.0407 (17)0.0458 (18)0.0261 (18)0.0064 (15)0.0042 (14)0.0053 (15)
O20.0303 (13)0.0297 (13)0.034 (2)0.0053 (11)0.0053 (14)0.0026 (14)
N10.044 (2)0.0304 (18)0.035 (2)0.0091 (18)0.0023 (19)0.0006 (19)
C30.059 (4)0.127 (7)0.063 (5)0.037 (4)0.020 (4)0.015 (5)
C40.053 (3)0.072 (4)0.060 (4)0.034 (3)0.002 (3)0.019 (3)
C50.037 (2)0.037 (2)0.035 (3)0.0113 (19)0.000 (2)0.003 (2)
C60.0235 (18)0.030 (2)0.023 (2)0.0021 (15)0.0022 (15)0.0045 (18)
C70.0256 (17)0.0225 (17)0.021 (2)0.0011 (14)0.0039 (15)0.0038 (15)
C80.030 (2)0.028 (2)0.024 (2)0.0008 (16)0.0084 (17)0.0049 (18)
C90.032 (2)0.035 (2)0.028 (2)0.0068 (18)0.0033 (18)0.0074 (19)
C100.046 (3)0.041 (3)0.032 (3)0.016 (2)0.007 (2)0.013 (2)
C110.056 (3)0.037 (3)0.057 (4)0.006 (2)0.011 (3)0.025 (2)
C20.045 (3)0.120 (7)0.072 (5)0.000 (4)0.026 (3)0.008 (5)
C10.033 (2)0.053 (3)0.041 (3)0.007 (2)0.005 (2)0.000 (3)
C140.0254 (19)0.032 (2)0.030 (2)0.0037 (16)0.0052 (17)0.0012 (18)
C130.040 (2)0.026 (2)0.036 (4)0.0070 (16)0.004 (2)0.0038 (17)
C120.057 (3)0.026 (2)0.055 (4)0.009 (2)0.005 (3)0.011 (2)
C150.069 (4)0.039 (3)0.061 (4)0.019 (3)0.017 (3)0.008 (3)
Geometric parameters (Å, º) top
Br1—C101.902 (6)C6—C71.528 (5)
O1—C11.226 (8)C7—C81.518 (5)
O3—C141.219 (6)C7—C141.544 (6)
O2—C71.414 (5)C8—C91.388 (7)
O2—H20.8200C8—C131.392 (6)
N1—C141.340 (6)C9—C101.395 (7)
N1—C131.406 (7)C9—H90.9300
N1—C151.456 (7)C10—C111.392 (9)
C3—C21.453 (12)C11—C121.377 (9)
C3—C41.503 (12)C11—H110.9300
C3—H3A0.9700C2—C11.504 (9)
C3—H3B0.9700C2—H2A0.9700
C4—C51.499 (7)C2—H2B0.9700
C4—H4A0.9700C13—C121.382 (7)
C4—H4B0.9700C12—H120.9300
C5—C61.330 (7)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C11.464 (7)C15—H15C0.9600
C7—O2—H2109.5C8—C9—H9121.5
C14—N1—C13111.3 (4)C10—C9—H9121.5
C14—N1—C15123.6 (5)C11—C10—C9122.2 (5)
C13—N1—C15125.1 (5)C11—C10—Br1119.6 (4)
C2—C3—C4112.8 (6)C9—C10—Br1118.1 (4)
C2—C3—H3A109.0C12—C11—C10120.1 (4)
C4—C3—H3A109.0C12—C11—H11119.9
C2—C3—H3B109.0C10—C11—H11119.9
C4—C3—H3B109.0C3—C2—C1113.6 (6)
H3A—C3—H3B107.8C3—C2—H2A108.9
C5—C4—C3112.0 (5)C1—C2—H2A108.9
C5—C4—H4A109.2C3—C2—H2B108.9
C3—C4—H4A109.2C1—C2—H2B108.9
C5—C4—H4B109.2H2A—C2—H2B107.7
C3—C4—H4B109.2O1—C1—C6120.4 (5)
H4A—C4—H4B107.9O1—C1—C2122.5 (6)
C6—C5—C4123.6 (5)C6—C1—C2117.1 (5)
C6—C5—H5118.2O3—C14—N1125.7 (4)
C4—C5—H5118.2O3—C14—C7125.0 (4)
C5—C6—C1120.5 (4)N1—C14—C7109.2 (4)
C5—C6—C7121.6 (4)C12—C13—C8121.7 (5)
C1—C6—C7117.7 (4)C12—C13—N1128.5 (4)
O2—C7—C8111.2 (3)C8—C13—N1109.7 (4)
O2—C7—C6111.9 (3)C11—C12—C13118.3 (5)
C8—C7—C6117.4 (3)C11—C12—H12120.9
O2—C7—C14104.5 (3)C13—C12—H12120.9
C8—C7—C14101.0 (3)N1—C15—H15A109.5
C6—C7—C14109.5 (3)N1—C15—H15B109.5
C9—C8—C13120.7 (4)H15A—C15—H15B109.5
C9—C8—C7130.5 (4)N1—C15—H15C109.5
C13—C8—C7108.6 (4)H15A—C15—H15C109.5
C8—C9—C10116.9 (5)H15B—C15—H15C109.5
C2—C3—C4—C545.4 (9)C5—C6—C1—C23.5 (8)
C3—C4—C5—C618.6 (9)C7—C6—C1—C2177.9 (6)
C4—C5—C6—C12.3 (8)C3—C2—C1—O1148.5 (8)
C4—C5—C6—C7171.9 (5)C3—C2—C1—C631.0 (10)
C5—C6—C7—O21.3 (6)C13—N1—C14—O3179.3 (4)
C1—C6—C7—O2175.7 (4)C15—N1—C14—O32.8 (8)
C5—C6—C7—C8131.6 (5)C13—N1—C14—C73.8 (5)
C1—C6—C7—C854.0 (6)C15—N1—C14—C7179.7 (5)
C5—C6—C7—C14114.1 (5)O2—C7—C14—O366.0 (5)
C1—C6—C7—C1460.3 (5)C8—C7—C14—O3178.5 (4)
O2—C7—C8—C968.7 (5)C6—C7—C14—O354.0 (5)
C6—C7—C8—C962.0 (6)O2—C7—C14—N1110.9 (4)
C14—C7—C8—C9179.1 (4)C8—C7—C14—N14.6 (4)
O2—C7—C8—C13106.6 (4)C6—C7—C14—N1129.1 (4)
C6—C7—C8—C13122.7 (4)C9—C8—C13—C121.1 (7)
C14—C7—C8—C133.8 (4)C7—C8—C13—C12177.0 (4)
C13—C8—C9—C100.7 (6)C9—C8—C13—N1177.7 (4)
C7—C8—C9—C10175.5 (4)C7—C8—C13—N11.9 (5)
C8—C9—C10—C110.1 (7)C14—N1—C13—C12180.0 (5)
C8—C9—C10—Br1179.3 (3)C15—N1—C13—C123.5 (8)
C9—C10—C11—C120.6 (8)C14—N1—C13—C81.3 (5)
Br1—C10—C11—C12178.9 (4)C15—N1—C13—C8177.7 (5)
C4—C3—C2—C152.1 (10)C10—C11—C12—C130.2 (8)
C5—C6—C1—O1176.1 (6)C8—C13—C12—C110.6 (8)
C7—C6—C1—O11.6 (8)N1—C13—C12—C11178.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.932.543.115 (7)120
O2—H2···O3i0.822.012.785 (5)156
Symmetry code: (i) x+1, y+1, z1/2.
Experimental (X-ray crystallography) and optimized (PM7) bond lengths (Å) involving the non-H atoms of IS1 top
ParametersOptimizedExperimental
C17—C161.2401.217 (5)
O1—C11.2181.220 (2)
O3—C141.2311.221 (3)
O2—C71.3941.420 (2)
N1—C141.3441.350 (3)
N1—C131.3831.410 (3)
N1—C151.4211.456 (3)
C8—C71.5061.510 (3)
C8—C131.3491.392 (3)
C8—C91.3781.371 (3)
C7—C61.5161.517 (3)
C7—C141.5201.553 (3)
C1—C61.4461.476 (3)
C6—C51.3371.332 (3)
C13—C121.3751.378 (3)
C5—C41.4711.495 (3)
C2—C31.4821.512 (3)
C3—C41.4681.506 (3)
C9—C101.3721.397 (3)
C11—C121.3671.387 (4)
C11—C101.3571.370 (4)
C15—C161.3591.467 (4)
Experimental (X-ray crystallography) and optimized (PM7) bond lengths (Å) involving the non-H atoms of IS2 top
ParametersOptimizedExperimental
C1—O11.2291.213 (2)
C1—C21.5151.507 (5)
C1—C61.4991.465 (3)
C2—C31.5181.514 (7)
C3—C41.5211.528 (8)
C4—C51.4991.486 (6)
C5—C61.3511.325 (3)
C6—C71.5111.511 (2)
C7—C81.5061.505 (2)
C7—C141.5671.544 (2)
C7—O21.4371.4190 (19)
C8—C91.3881.370 (3)
C8—C131.4011.385 (3)
C9—C101.3951.390 (3)
C10—C111.4051.368 (3)
C11—C121.3991.378 (3)
C12—C131.3831.371 (3)
C13—N11.4031.409 (2)
C14—N11.4001.352 (2)
C14—O31.2261.220 (2)
C15—C161.5191.478 (3)
C15—N11.4431.457 (3)
Experimental (X-ray crystallography) and optimized (PM7) bond lengths (Å) involving the non-H atoms of IS3 (Å) top
ParametersOptimizedExperimental
Br1—C101.8931.902 (6)
O1—C11.2281.226 (8)
O3—C141.2311.219 (6)
O2—C71.4341.414 (5)
N1—C141.3921.340 (6)
N1—C131.3951.406 (7)
N1—C151.4341.456 (7)
C3—C41.5211.503 (12)
C3—C21.5151.453 (12)
C4—C51.4901.499 (7)
C5—C61.3491.330 (7)
C6—C71.5051.528 (5)
C6—C11.4941.464 (7)
C7—C81.5101.518 (5)
C7—C141.5501.544 (6)
C8—C91.3881.388 (7)
C8—C131.4031.392 (6)
C9—C101.3991.395 (7)
C10—C111.4051.392 (9)
C2—C11.5131.504 (9)
C11—C121.3821.377 (9)
C13—C121.3811.382 (7)
Experimental (X-ray crystallography) and optimized (PM7) bond angles (°) involving the non-H atoms of IS1 top
ParametersOptimizedExperimental
O2—C7—C6114.98111.89 (16)
O2—C7—C14109.32107.55 (15)
O1—C1—C6120.84120.88 (19)
O3—C14—N1124.02126.47 (19)
C14—N1—C15125.01124.0 (2)
N1—C13—C12128.41128.1 (2)
C7—C8—C13110.24109.08 (18)
C8—C7—C6113.58114.55 (16)
C8—C7—C1498.94101.10 (16)
C13—C8—C9119.77119.8 (2)
C12—C11—C10120.42121.5 (2)
O2—C7—C8106.07108.55 (16)
O1—C1—C2120.67121.29 (19)
O3—C14—C7125.14124.63 (18)
C8—C13—C12121.03122.2 (2)
C9—C10—C11120.33120.8 (2)
Experimental (X-ray crystallography) and optimized (PM7) bond angles (°) involving the non-H atoms of IS2 top
ParametersOptimizedExperimental
C6—C1—O1121.10121.48 (17)
C7—C8—C13109.68109.25 (15)
C7—C14—O3125.22125.90 (16)
C8—C9—C10118.21118.5 (2)
C8—C13—C12121.20121.61 (19)
C9—C10—C11120.62120.1 (2)
C11—C12—C13118.04117.3 (2)
C12—C13—N1128.74128.59 (18)
C13—N1—C14111.04110.60 (15)
C13—N1—C15125.44126.72 (16)
C16—C15—N1112.50113.4 (2)
C14—N1—C15123.51122.69 (17)
N1—C14—O3127.35124.92 (17)
Experimental (X-ray crystallography) and optimized (PM7) bond angles (°) involving the non-H atoms of IS3 top
ParametersOptimizedExperimental
O1—C1—C6120.97120.4 (5)
Br1—C10—C9121.81118.1 (4)
O3—C14—C7127.76125.0 (4)
O2—C7—C6112111.9 (3)
N1—C13—C12128.48128.5 (4)
C7—C8—C9132.04130.5 (4)
C8—C7—C14103.09101.0 (3)
C8—C9—C10121.49116.9 (5)
C8—C13—C12120.89121.7 (5)
C9—C10—C11117.34122.2 (5)
C10—C11—C12121.62120.1 (4)
N1—C14—C7105.49109.2 (4)
C11—C12—C13119.35118.3 (5)
Br1—C10—C11119.05119.6 (4)
O3—C14—N1126.55125.7 (4)
Mulliken atomic charges of IS1 top
NoAtomChargeNoAtomCharge
1C17-0.374512C11-0.1224
2O2-0.544613C4-0.3959
3O1-0.481014C12-0.2986
4O3-0.497615C10-0.2727
5N1-0.611316C15-0.1100
6C8-0.158317C16-0.2432
7C6-0.256918C10.5185
8C5-0.059319C140.6083
9C2-0.469720C130.2769
10C3-0.335121C70.2383
11C9-0.0997
Mulliken atomic charges of IS2 top
NoAtomChargeNoAtomCharge
1C2-0.471711C15-0.0829
2C3-0.333312C16-0.6165
3C4-0.395213N1-0.6074
4C5-0.060014O1-0.4818
5C6-0.260115O2-0.5427
6C8-0.161916O3-0.4887
7C9-0.100017C10.5162
8C10-0.273718C70.2314
9C11-0.122319C130.2721
10C12-0.301320C140.6103
Mulliken atomic charges of IS3 top
NoAtomChargeNoAtomCharge
1C2-0.471212C16-0.6165
2C3-0.333413N1-0.6063
3C4-0.401014O1-0.4820
4C5-0.030715O2-0.5471
5C6-0.251516O3-0.4462
6C8-0.218417C10.5151
7C9-0.134018C70.2608
8C10-0.516819C130.2896
9C11-0.150920C140.5952
10C12-0.297721Br0.4344
11C15-0.3149
Quantum chemical parameters of IS1, IS2 and IS3 top
ParametersUnitsIS1IS2IS3
EHOMOeV-8.661-8.584-8.706
ELUMOeV-0.355-0.324-0.463
Energy gap (ELUMOEHOMO)eV8.3068.2608.243
Electronic energyeV-25238.3454-24210.9893-23758.9724
Chemical potential (µ)eV-4.508-4.454-4.585
Global hardness (η)eV4.1534.1304.121
Global softness (S)eV-10.11180.1210.121
Electrophilicity index (ω)eV2.2522.4022.550
Electronegativity (χ)eV4.5084.4544.584
Dipole (µ)Debye4.3033.7711.450
Static second-order hyperpolarizability (γ)10–35 esu1.88890.92131.2904
Druglikeness of IS1, IS2 and IS3 top
Compoundslog PTPSAMWVolumenONnOH-NHnrotbNo. violations
IS11.9957.61283.33259.994130
IS21.7257.61271.32248.824120
IS32.1357.61336.19249.901110
Bioactive scores for IS1, IS2 and IS3. The column headings are defined as: G protein-coupled receptors (GPCR) ligand activity, ion channel modulation (ICM), kinase inhibition activity (KI), nuclear receptor ligand activity (NR), protease inhibitor (PI) and enzyme inhibitor (EI). top
CompoundsGPCRICMKINRPIEI
IS1-0.29-0.52-1.04-0.22-0.59-0.31
IS2-0.29-0.60-1.02-0.24-0.63-0.30
IS3-0.46-0.64-1.05-0.40-0.69-0.33
Diameter of the inhibition zone (mm) of compounds IS1, IS2 and IS3 towards Eschericia coli, Proteus Vulgaris, Shigella flexneri, staphylococcus aureus and Micrococcus luteus. top
CompoundsE. coliP. vulgarisS. flexneriS. aureusM. luteus
IS11010101213
IS21311121314
IS31413141515
Diameter of the inhibition zone (mm) of compounds IS1, IS2 and IS3 towards Aspergillus niger top
CompoundAspergillus nigerCompoundAspergillus niger
IS116IS318
IS217
Molecular docking interactions of IS1, IS2 and IS3 against PBP2a top
InhibitorBinding energy (K cal mol-1)Distance (Å)Inhibition constant (µM)Binding site of proteinBinding site of ligand
IS1-6.112.94,2.8433.27OH (Thr600), COOH (Glu447)Aliphatic CHCO
IS2-7.372.43,2.79,2.69,2.853.95COOH (Glu447), COOH (Gln521), NH2 (Gln521), NH2(Gln521)OH, CO, CO, α,β-unsaturated ketone
IS3-7.232.86,3.24,2.89,3.09,3.3514.69NH2 (Ser400), COOH (Thr399), COOH (Glu602), NH2 (Lys604), NH2 (Asn632)OH, Ar-CH, N-CH3, N-CH3, Br
 

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