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A four-stage reaction sequence has been designed and developed for the synthesis of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds of potential pharmaceutical value. The sequence starts with simple commercially available indoles and proceeds via 3-(indol-3-yl)-3-oxo­propane­nitriles, which react with 2-bromo­benzaldehyde to form the corresponding chalcones; these are readily reduced to di­hydro­chalcones, which are in turn acyl­ated to form the enolate esters. The com­pounds in this sequence have been characterized by IR and 1H and 13C NMR spectroscopy, by mass spectrometry and by elemental analysis. The mol­ecular and supra­molecular structures are reported for representative examples, namely (E)-3-(2-bromo­phen­yl)-2-(1-methyl-1H-indole-3-carbon­yl)acrylo­nitrile, C19H13BrN2O, (Ib), (2RS)-2-(2-bromo­benz­yl)-3-(1-methyl-1H-in­dol-3-yl)-3-oxo­propane­nitrile, C19H15BrN2O, (IIb), and (2RS)-3-(1-benzyl-1H-indol-3-yl)-2-(2-bromo­benz­yl)-3-oxo­propane­nitrile, C25H19BrN2O, (IIc), the latter two of which crystallize with Z′ = 2, and (E)-1-(1-acetyl-1H-indol-3-yl)-3-(2-bromo­phen­yl)-2-cyano­prop-1-en-1-yl acetate, C22H17BrN2O, (III), and (E)-1-(1-benzyl-1H-indol-3-yl)-3-(2-bromo­phen­yl)-2-cyano­prop-1-en-1-yl ben­zoate, C32H23BrN2O, (IV). The structure of the related chalcone (E)-2-benzoyl-3-(2-bromo­phen­yl)prop-2-ene­nitrile, (V), has been redetermined at 100 K, where it is monoclinic, as opposed to the triclinic form reported at ambient temperature.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617015789/yf3130sup1.cif
Contains datablocks global, Ib, IIb, IIc, III, IV, V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130Ibsup2.hkl
Contains datablock Ib

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130IIbsup3.hkl
Contains datablock IIb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130IIcsup4.hkl
Contains datablock IIc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130IIIsup5.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130IVsup6.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015789/yf3130Vsup7.hkl
Contains datablock V

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130Ibsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130IIbsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130IIcsup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130IIIsup11.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130IVsup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617015789/yf3130Vsup13.cml
Supplementary material

CCDC references: 1582887; 1582886; 1582885; 1582884; 1582883; 1582882

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-3-(2-Bromophenyl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile (Ib) top
Crystal data top
C19H13BrN2OZ = 2
Mr = 365.22F(000) = 368
Triclinic, P1Dx = 1.628 Mg m3
a = 9.188 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.308 (5) ÅCell parameters from 3467 reflections
c = 10.887 (5) Åθ = 2.5–27.7°
α = 113.56 (2)°µ = 2.76 mm1
β = 90.782 (18)°T = 100 K
γ = 116.173 (16)°Block, yellow
V = 745.3 (7) Å30.33 × 0.21 × 0.19 mm
Data collection top
Bruker D8 Venture
diffractometer
3467 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3296 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.040
φ and ω scansθmax = 27.7°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1111
Tmin = 0.446, Tmax = 0.591k = 1212
46632 measured reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.049 w = 1/[σ2(Fo2) + (0.0202P)2 + 0.6373P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3467 reflectionsΔρmax = 0.40 e Å3
209 parametersΔρmin = 0.39 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.29057 (17)0.14946 (19)0.81720 (15)0.0189 (3)
C10.41876 (18)0.2564 (2)0.82078 (15)0.0119 (3)
C20.57679 (18)0.39150 (19)0.82260 (14)0.0100 (3)
C30.72260 (18)0.40212 (19)0.86046 (14)0.0098 (3)
H30.81790.49240.85130.012*
C280.58375 (18)0.52896 (19)0.77826 (14)0.0098 (3)
O280.71080 (13)0.67527 (14)0.82765 (11)0.0150 (2)
N210.21687 (15)0.33281 (16)0.50736 (12)0.0101 (2)
C220.31281 (17)0.31821 (19)0.59208 (14)0.0100 (3)
H220.29160.20880.59230.012*
C230.44624 (17)0.48493 (18)0.67852 (14)0.0087 (3)
C23A0.43162 (17)0.61089 (19)0.64119 (14)0.0090 (3)
C240.52727 (18)0.79570 (19)0.68562 (14)0.0105 (3)
H240.62620.86600.75650.013*
C250.47404 (19)0.87307 (19)0.62369 (15)0.0126 (3)
H250.53860.99820.65190.015*
C260.32693 (19)0.7718 (2)0.51994 (15)0.0131 (3)
H260.29340.83020.48070.016*
C270.22994 (18)0.5887 (2)0.47382 (15)0.0120 (3)
H270.13030.51940.40370.014*
C27A0.28581 (17)0.51137 (19)0.53536 (14)0.0094 (3)
C2110.07277 (18)0.1855 (2)0.39592 (16)0.0150 (3)
H21A0.04970.07160.39490.022*
H21B0.09630.18290.30770.022*
H21C0.02440.20290.41030.022*
C310.75642 (17)0.29564 (18)0.91350 (14)0.0091 (3)
C320.88829 (17)0.25981 (18)0.88333 (14)0.0092 (3)
Br321.00583 (2)0.32293 (2)0.75519 (2)0.01222 (5)
C330.93663 (18)0.17583 (19)0.94167 (15)0.0114 (3)
H331.02700.15420.91950.014*
C340.85086 (18)0.1236 (2)1.03316 (15)0.0127 (3)
H340.88310.06691.07510.015*
C350.71789 (19)0.1542 (2)1.06365 (15)0.0130 (3)
H350.65850.11671.12550.016*
C360.67111 (18)0.2388 (2)1.00457 (15)0.0116 (3)
H360.57970.25861.02630.014*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0142 (6)0.0248 (7)0.0258 (7)0.0094 (6)0.0057 (5)0.0187 (6)
C10.0131 (7)0.0160 (7)0.0128 (7)0.0096 (6)0.0042 (5)0.0092 (6)
C20.0114 (7)0.0103 (6)0.0092 (6)0.0055 (6)0.0033 (5)0.0050 (5)
C30.0109 (6)0.0092 (6)0.0086 (6)0.0044 (5)0.0021 (5)0.0039 (5)
C280.0111 (6)0.0108 (6)0.0096 (6)0.0068 (5)0.0041 (5)0.0048 (5)
O280.0135 (5)0.0108 (5)0.0181 (5)0.0036 (4)0.0017 (4)0.0067 (4)
N210.0087 (5)0.0106 (6)0.0105 (6)0.0039 (5)0.0019 (5)0.0053 (5)
C220.0115 (6)0.0121 (7)0.0105 (6)0.0073 (6)0.0051 (5)0.0070 (6)
C230.0092 (6)0.0099 (6)0.0097 (6)0.0059 (5)0.0045 (5)0.0055 (5)
C23A0.0097 (6)0.0120 (7)0.0086 (6)0.0068 (5)0.0046 (5)0.0058 (5)
C240.0107 (6)0.0105 (7)0.0088 (6)0.0050 (6)0.0026 (5)0.0031 (5)
C250.0154 (7)0.0097 (6)0.0125 (7)0.0066 (6)0.0050 (6)0.0043 (6)
C260.0175 (7)0.0170 (7)0.0133 (7)0.0125 (6)0.0061 (6)0.0098 (6)
C270.0116 (7)0.0153 (7)0.0108 (7)0.0075 (6)0.0025 (5)0.0064 (6)
C27A0.0105 (6)0.0110 (6)0.0093 (6)0.0063 (5)0.0051 (5)0.0056 (5)
C2110.0111 (7)0.0123 (7)0.0134 (7)0.0015 (6)0.0020 (6)0.0035 (6)
C310.0082 (6)0.0079 (6)0.0086 (6)0.0027 (5)0.0002 (5)0.0030 (5)
C320.0078 (6)0.0090 (6)0.0082 (6)0.0019 (5)0.0010 (5)0.0039 (5)
Br320.01107 (7)0.01656 (8)0.01307 (8)0.00725 (6)0.00570 (5)0.00963 (6)
C330.0092 (6)0.0110 (7)0.0129 (7)0.0048 (5)0.0012 (5)0.0047 (6)
C340.0134 (7)0.0117 (7)0.0134 (7)0.0050 (6)0.0003 (5)0.0074 (6)
C350.0137 (7)0.0140 (7)0.0123 (7)0.0055 (6)0.0038 (5)0.0082 (6)
C360.0099 (6)0.0140 (7)0.0115 (7)0.0062 (6)0.0027 (5)0.0059 (6)
Geometric parameters (Å, º) top
N1—C11.146 (2)C25—H250.9500
C1—C21.435 (2)C26—C271.384 (2)
C2—C31.345 (2)C26—H260.9500
C2—C281.516 (2)C27—C27A1.390 (2)
C3—C311.462 (2)C27—H270.9500
C3—H30.9500C211—H21A0.9800
C28—O281.2253 (19)C211—H21B0.9800
C28—C231.447 (2)C211—H21C0.9800
N21—C221.3528 (19)C31—C361.397 (2)
N21—C27A1.385 (2)C31—C321.402 (2)
N21—C2111.459 (2)C32—C331.381 (2)
C22—C231.385 (2)C32—Br321.8959 (15)
C22—H220.9500C33—C341.385 (2)
C23—C23A1.441 (2)C33—H330.9500
C23A—C241.398 (2)C34—C351.388 (2)
C23A—C27A1.411 (2)C34—H340.9500
C24—C251.379 (2)C35—C361.384 (2)
C24—H240.9500C35—H350.9500
C25—C261.405 (2)C36—H360.9500
N1—C1—C2178.21 (16)C26—C27—C27A116.53 (14)
C3—C2—C1123.11 (14)C26—C27—H27121.7
C3—C2—C28117.10 (13)C27A—C27—H27121.7
C1—C2—C28119.78 (13)N21—C27A—C27128.84 (14)
C2—C3—C31129.71 (13)N21—C27A—C23A108.03 (12)
C2—C3—H3115.1C27—C27A—C23A123.12 (14)
C31—C3—H3115.1N21—C211—H21A109.5
O28—C28—C23122.07 (13)N21—C211—H21B109.5
O28—C28—C2117.42 (13)H21A—C211—H21B109.5
C23—C28—C2120.49 (13)N21—C211—H21C109.5
C22—N21—C27A108.76 (12)H21A—C211—H21C109.5
C22—N21—C211126.51 (13)H21B—C211—H21C109.5
C27A—N21—C211124.52 (12)C36—C31—C32116.99 (13)
N21—C22—C23110.62 (13)C36—C31—C3122.58 (13)
N21—C22—H22124.7C32—C31—C3120.20 (13)
C23—C22—H22124.7C33—C32—C31122.72 (13)
C22—C23—C23A105.98 (13)C33—C32—Br32117.14 (11)
C22—C23—C28128.88 (13)C31—C32—Br32120.13 (11)
C23A—C23—C28124.91 (13)C32—C33—C34118.77 (14)
C24—C23A—C27A119.08 (13)C32—C33—H33120.6
C24—C23A—C23134.34 (14)C34—C33—H33120.6
C27A—C23A—C23106.58 (13)C33—C34—C35120.09 (13)
C25—C24—C23A118.17 (14)C33—C34—H34120.0
C25—C24—H24120.9C35—C34—H34120.0
C23A—C24—H24120.9C36—C35—C34120.46 (14)
C24—C25—C26121.77 (14)C36—C35—H35119.8
C24—C25—H25119.1C34—C35—H35119.8
C26—C25—H25119.1C35—C36—C31120.95 (14)
C27—C26—C25121.31 (14)C35—C36—H36119.5
C27—C26—H26119.3C31—C36—H36119.5
C25—C26—H26119.3
C1—C2—C3—C314.1 (2)C22—N21—C27A—C27179.90 (14)
C28—C2—C3—C31176.84 (13)C211—N21—C27A—C274.9 (2)
C3—C2—C28—O2828.16 (19)C22—N21—C27A—C23A0.57 (15)
C1—C2—C28—O28152.77 (14)C211—N21—C27A—C23A174.47 (13)
C3—C2—C28—C23150.23 (14)C26—C27—C27A—N21178.17 (14)
C1—C2—C28—C2328.8 (2)C26—C27—C27A—C23A1.1 (2)
C27A—N21—C22—C230.38 (16)C24—C23A—C27A—N21178.21 (12)
C211—N21—C22—C23175.30 (13)C23—C23A—C27A—N211.26 (15)
N21—C22—C23—C23A1.15 (16)C24—C23A—C27A—C271.2 (2)
N21—C22—C23—C28175.81 (13)C23—C23A—C27A—C27179.37 (13)
O28—C28—C23—C22164.56 (14)C2—C3—C31—C3638.0 (2)
C2—C28—C23—C2213.7 (2)C2—C3—C31—C32147.66 (16)
O28—C28—C23—C23A9.2 (2)C36—C31—C32—C331.3 (2)
C2—C28—C23—C23A172.51 (13)C3—C31—C32—C33173.30 (13)
C22—C23—C23A—C24177.89 (15)C36—C31—C32—Br32177.45 (10)
C28—C23—C23A—C243.0 (2)C3—C31—C32—Br327.92 (18)
C22—C23—C23A—C27A1.45 (15)C31—C32—C33—C340.4 (2)
C28—C23—C23A—C27A176.39 (13)Br32—C32—C33—C34178.40 (11)
C27A—C23A—C24—C250.2 (2)C32—C33—C34—C350.7 (2)
C23—C23A—C24—C25179.45 (15)C33—C34—C35—C360.8 (2)
C23A—C24—C25—C260.9 (2)C34—C35—C36—C310.1 (2)
C24—C25—C26—C271.0 (2)C32—C31—C36—C351.2 (2)
C25—C26—C27—C27A0.0 (2)C3—C31—C36—C35173.32 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24···Cg1i0.952.773.544 (3)139
Symmetry code: (i) x, y+1, z.
(2RS)-2-(2-Bromobenzyl)-3-(1-methyl-1H-indol-3-yl)-\ 3-oxopropanenitrile (IIb) top
Crystal data top
C19H15BrN2OF(000) = 1488
Mr = 367.24Dx = 1.539 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.728 (6) ÅCell parameters from 7297 reflections
b = 14.901 (6) Åθ = 2.4–27.6°
c = 15.507 (6) ŵ = 2.60 mm1
β = 92.165 (19)°T = 100 K
V = 3170 (2) Å3Plate, yellow-brown
Z = 80.40 × 0.30 × 0.10 mm
Data collection top
Bruker D8 Venture
diffractometer
7297 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube5456 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.090
φ and ω scansθmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1717
Tmin = 0.489, Tmax = 0.771k = 1819
79963 measured reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0217P)2 + 3.7392P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
7297 reflectionsΔρmax = 0.54 e Å3
417 parametersΔρmin = 0.76 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.18232 (18)0.42519 (15)0.29826 (14)0.0248 (5)
C110.2371 (2)0.47754 (16)0.27615 (16)0.0168 (5)
C120.30553 (18)0.54607 (16)0.24554 (15)0.0133 (5)
H120.27250.60590.24380.016*
C130.33425 (18)0.51972 (15)0.15332 (15)0.0133 (5)
O130.34791 (14)0.44049 (11)0.13777 (11)0.0198 (4)
C1270.39870 (19)0.55156 (16)0.30549 (15)0.0146 (5)
H12A0.43370.49360.30350.018*
H12B0.44230.59850.28340.018*
C1210.37709 (18)0.57268 (16)0.39815 (16)0.0134 (5)
C1220.35456 (18)0.65859 (16)0.42667 (16)0.0131 (5)
Br120.34405 (2)0.75572 (2)0.34672 (2)0.01692 (7)
C1230.33681 (19)0.67677 (17)0.51225 (16)0.0153 (5)
H1230.32230.73610.53000.018*
C1240.34047 (19)0.60709 (17)0.57167 (16)0.0186 (6)
H1240.32840.61880.63050.022*
C1250.3616 (2)0.52069 (17)0.54579 (17)0.0194 (6)
H1250.36360.47300.58650.023*
C1260.37979 (19)0.50432 (17)0.45965 (16)0.0181 (5)
H1260.39450.44490.44220.022*
N1310.33943 (15)0.72482 (13)0.02457 (13)0.0130 (4)
C1320.32742 (18)0.68181 (16)0.10035 (15)0.0129 (5)
H1320.31000.71000.15250.016*
C1330.34426 (18)0.59041 (16)0.09058 (15)0.0132 (5)
C13A0.36750 (18)0.57742 (16)0.00110 (15)0.0126 (5)
C1340.38778 (18)0.50255 (17)0.04959 (15)0.0156 (5)
H1340.39060.44420.02500.019*
C1350.40367 (19)0.51530 (18)0.13629 (17)0.0196 (6)
H1350.41650.46490.17160.024*
C1360.40119 (19)0.60133 (18)0.17306 (16)0.0196 (6)
H1360.41340.60810.23260.023*
C1370.38127 (19)0.67663 (17)0.12446 (16)0.0163 (5)
H1370.37980.73500.14920.020*
C17A0.36354 (18)0.66288 (16)0.03762 (15)0.0132 (5)
C1310.3262 (2)0.82032 (16)0.00842 (17)0.0190 (6)
H13A0.30950.85040.06210.029*
H13B0.27340.82910.03510.029*
H13C0.38670.84570.01260.029*
N210.22989 (19)0.33176 (16)0.79585 (15)0.0273 (6)
C210.2823 (2)0.27789 (16)0.77344 (16)0.0164 (5)
C220.34802 (18)0.20737 (16)0.74254 (15)0.0126 (5)
H220.31330.14840.74230.015*
C230.37571 (18)0.23082 (15)0.64954 (15)0.0137 (5)
O230.39429 (14)0.30937 (11)0.63232 (11)0.0198 (4)
C2270.44284 (18)0.20000 (16)0.79972 (15)0.0140 (5)
H22A0.48480.15270.77600.017*
H22B0.47870.25750.79730.017*
C2210.42413 (18)0.17826 (16)0.89260 (15)0.0130 (5)
C2220.40507 (18)0.09155 (16)0.92183 (15)0.0138 (5)
Br220.39344 (2)0.00513 (2)0.84159 (2)0.01913 (7)
C2230.39041 (19)0.07332 (17)1.00809 (16)0.0166 (5)
H2230.37970.01351.02660.020*
C2240.39156 (19)0.14326 (17)1.06685 (16)0.0177 (5)
H2240.38110.13131.12600.021*
C2250.40795 (19)0.23065 (17)1.04010 (16)0.0177 (5)
H2250.40740.27871.08040.021*
C2260.42517 (18)0.24722 (16)0.95389 (16)0.0159 (5)
H2260.43800.30690.93600.019*
N2310.36915 (16)0.02132 (13)0.52880 (13)0.0140 (4)
C2320.35817 (18)0.06868 (16)0.60173 (15)0.0136 (5)
H2320.33810.04420.65480.016*
C2330.38029 (18)0.15829 (15)0.58849 (15)0.0126 (5)
C23A0.40570 (18)0.16573 (16)0.49902 (15)0.0133 (5)
C2340.43411 (19)0.23648 (17)0.44611 (16)0.0180 (5)
H2340.44020.29580.46820.022*
C2350.4530 (2)0.21792 (19)0.36101 (17)0.0231 (6)
H2350.47080.26550.32400.028*
C2360.4466 (2)0.13043 (19)0.32817 (17)0.0237 (6)
H2360.46150.11980.26970.028*
C2370.41896 (19)0.05918 (18)0.37893 (16)0.0190 (6)
H2370.41440.00020.35680.023*
C27A0.39814 (18)0.07874 (16)0.46411 (15)0.0143 (5)
C2310.3488 (2)0.07415 (16)0.51695 (17)0.0177 (5)
H23A0.33220.10070.57230.027*
H23B0.40650.10410.49530.027*
H23C0.29390.08170.47530.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0269 (14)0.0297 (12)0.0177 (12)0.0120 (11)0.0031 (10)0.0050 (10)
C110.0179 (15)0.0211 (13)0.0111 (12)0.0018 (11)0.0050 (10)0.0003 (10)
C120.0141 (14)0.0124 (11)0.0133 (12)0.0004 (9)0.0005 (10)0.0006 (9)
C130.0116 (13)0.0140 (12)0.0142 (12)0.0020 (9)0.0007 (10)0.0007 (9)
O130.0268 (11)0.0137 (9)0.0189 (9)0.0008 (8)0.0017 (8)0.0017 (7)
C1270.0138 (14)0.0134 (11)0.0166 (12)0.0003 (10)0.0009 (10)0.0030 (9)
C1210.0084 (13)0.0160 (12)0.0157 (12)0.0027 (10)0.0020 (10)0.0021 (9)
C1220.0092 (13)0.0160 (12)0.0139 (12)0.0031 (9)0.0021 (10)0.0011 (9)
Br120.02524 (15)0.01184 (11)0.01379 (12)0.00209 (10)0.00211 (10)0.00004 (9)
C1230.0123 (14)0.0182 (12)0.0152 (13)0.0036 (10)0.0026 (10)0.0023 (10)
C1240.0149 (14)0.0287 (14)0.0119 (12)0.0048 (11)0.0021 (10)0.0005 (10)
C1250.0158 (14)0.0234 (13)0.0186 (13)0.0012 (11)0.0044 (11)0.0083 (10)
C1260.0164 (14)0.0149 (12)0.0225 (13)0.0012 (10)0.0049 (10)0.0013 (10)
N1310.0130 (11)0.0134 (10)0.0125 (10)0.0015 (8)0.0028 (8)0.0008 (8)
C1320.0106 (13)0.0164 (12)0.0116 (12)0.0013 (9)0.0032 (10)0.0013 (9)
C1330.0116 (13)0.0150 (12)0.0127 (12)0.0009 (9)0.0010 (10)0.0001 (9)
C13A0.0085 (13)0.0163 (12)0.0128 (12)0.0021 (9)0.0022 (10)0.0002 (9)
C1340.0123 (13)0.0176 (12)0.0170 (12)0.0009 (10)0.0004 (10)0.0021 (10)
C1350.0133 (14)0.0265 (14)0.0191 (13)0.0007 (11)0.0019 (11)0.0081 (11)
C1360.0143 (14)0.0343 (15)0.0099 (12)0.0018 (11)0.0011 (10)0.0010 (10)
C1370.0116 (14)0.0231 (13)0.0138 (12)0.0025 (10)0.0032 (10)0.0032 (10)
C17A0.0074 (13)0.0164 (12)0.0155 (12)0.0020 (9)0.0042 (10)0.0014 (9)
C1310.0241 (16)0.0135 (12)0.0191 (13)0.0009 (11)0.0026 (11)0.0026 (10)
N210.0259 (15)0.0317 (13)0.0243 (13)0.0088 (11)0.0008 (11)0.0055 (10)
C210.0172 (14)0.0205 (12)0.0111 (12)0.0001 (11)0.0023 (10)0.0016 (10)
C220.0133 (13)0.0122 (11)0.0122 (12)0.0009 (9)0.0000 (10)0.0005 (9)
C230.0118 (13)0.0157 (12)0.0133 (12)0.0026 (10)0.0029 (10)0.0006 (9)
O230.0284 (12)0.0114 (8)0.0197 (10)0.0007 (7)0.0013 (8)0.0009 (7)
C2270.0127 (14)0.0147 (11)0.0145 (12)0.0006 (10)0.0017 (10)0.0005 (9)
C2210.0081 (13)0.0168 (12)0.0140 (12)0.0021 (9)0.0009 (10)0.0008 (9)
C2220.0126 (13)0.0155 (12)0.0130 (12)0.0032 (10)0.0037 (10)0.0019 (9)
Br220.03058 (16)0.01197 (12)0.01466 (12)0.00296 (11)0.00141 (10)0.00100 (9)
C2230.0155 (14)0.0176 (12)0.0165 (13)0.0019 (10)0.0025 (10)0.0039 (10)
C2240.0140 (14)0.0280 (13)0.0110 (12)0.0004 (11)0.0033 (10)0.0019 (10)
C2250.0135 (14)0.0226 (13)0.0168 (13)0.0003 (10)0.0040 (10)0.0066 (10)
C2260.0130 (13)0.0155 (11)0.0189 (12)0.0002 (10)0.0028 (10)0.0002 (10)
N2310.0160 (12)0.0124 (10)0.0135 (10)0.0012 (8)0.0028 (9)0.0027 (8)
C2320.0138 (14)0.0157 (11)0.0111 (12)0.0050 (10)0.0028 (10)0.0005 (9)
C2330.0094 (13)0.0158 (11)0.0124 (12)0.0033 (9)0.0028 (10)0.0009 (9)
C23A0.0091 (13)0.0183 (12)0.0123 (12)0.0039 (10)0.0022 (10)0.0002 (9)
C2340.0157 (14)0.0196 (13)0.0188 (13)0.0020 (10)0.0009 (10)0.0042 (10)
C2350.0196 (15)0.0330 (15)0.0169 (13)0.0001 (12)0.0021 (11)0.0058 (11)
C2360.0188 (16)0.0404 (16)0.0117 (13)0.0026 (12)0.0005 (11)0.0025 (11)
C2370.0122 (14)0.0295 (14)0.0149 (13)0.0022 (11)0.0044 (11)0.0086 (11)
C27A0.0094 (13)0.0200 (12)0.0132 (12)0.0025 (10)0.0044 (10)0.0007 (9)
C2310.0190 (15)0.0135 (12)0.0205 (13)0.0011 (10)0.0032 (11)0.0034 (10)
Geometric parameters (Å, º) top
N11—C111.145 (3)N21—C211.141 (3)
C11—C121.478 (3)C21—C221.476 (3)
C12—C131.548 (3)C22—C231.545 (3)
C12—C1271.555 (3)C22—C2271.551 (3)
C12—H121.0000C22—H221.0000
C13—O131.221 (3)C23—O231.229 (3)
C13—C1331.444 (3)C23—C2331.440 (3)
C127—C1211.511 (3)C227—C2211.508 (3)
C127—H12A0.9900C227—H22A0.9900
C127—H12B0.9900C227—H22B0.9900
C121—C1221.393 (3)C221—C2221.397 (3)
C121—C1261.395 (3)C221—C2261.399 (3)
C122—C1231.385 (3)C222—C2231.387 (3)
C122—Br121.908 (2)C222—Br221.906 (2)
C123—C1241.388 (3)C223—C2241.384 (4)
C123—H1230.9500C223—H2230.9500
C124—C1251.383 (4)C224—C2251.388 (4)
C124—H1240.9500C224—H2240.9500
C125—C1261.390 (4)C225—C2261.389 (3)
C125—H1250.9500C225—H2250.9500
C126—H1260.9500C226—H2260.9500
N131—C1321.354 (3)N231—C2321.346 (3)
N131—C17A1.384 (3)N231—C27A1.388 (3)
N131—C1311.455 (3)N231—C2311.460 (3)
C132—C1331.391 (3)C232—C2331.386 (3)
C132—H1320.9500C232—H2320.9500
C133—C13A1.449 (3)C233—C23A1.448 (3)
C13A—C1341.399 (3)C23A—C2341.400 (3)
C13A—C17A1.408 (3)C23A—C27A1.407 (3)
C134—C1351.383 (4)C234—C2351.382 (4)
C134—H1340.9500C234—H2340.9500
C135—C1361.403 (4)C235—C2361.401 (4)
C135—H1350.9500C235—H2350.9500
C136—C1371.385 (4)C236—C2371.383 (4)
C136—H1360.9500C236—H2360.9500
C137—C17A1.393 (3)C237—C27A1.393 (3)
C137—H1370.9500C237—H2370.9500
C131—H13A0.9800C231—H23A0.9800
C131—H13B0.9800C231—H23B0.9800
C131—H13C0.9800C231—H23C0.9800
N11—C11—C12178.2 (3)N21—C21—C22178.4 (3)
C11—C12—C13107.97 (19)C21—C22—C23108.47 (19)
C11—C12—C127111.3 (2)C21—C22—C227112.0 (2)
C13—C12—C127109.5 (2)C23—C22—C227108.6 (2)
C11—C12—H12109.4C21—C22—H22109.2
C13—C12—H12109.4C23—C22—H22109.2
C127—C12—H12109.4C227—C22—H22109.2
O13—C13—C133123.6 (2)O23—C23—C233123.9 (2)
O13—C13—C12118.3 (2)O23—C23—C22118.6 (2)
C133—C13—C12118.1 (2)C233—C23—C22117.5 (2)
C121—C127—C12113.1 (2)C221—C227—C22113.1 (2)
C121—C127—H12A109.0C221—C227—H22A109.0
C12—C127—H12A109.0C22—C227—H22A109.0
C121—C127—H12B109.0C221—C227—H22B109.0
C12—C127—H12B109.0C22—C227—H22B109.0
H12A—C127—H12B107.8H22A—C227—H22B107.8
C122—C121—C126117.0 (2)C222—C221—C226117.1 (2)
C122—C121—C127123.2 (2)C222—C221—C227123.3 (2)
C126—C121—C127119.8 (2)C226—C221—C227119.6 (2)
C123—C122—C121122.2 (2)C223—C222—C221122.0 (2)
C123—C122—Br12117.56 (18)C223—C222—Br22118.02 (18)
C121—C122—Br12120.21 (18)C221—C222—Br22119.95 (18)
C122—C123—C124119.1 (2)C224—C223—C222119.3 (2)
C122—C123—H123120.4C224—C223—H223120.4
C124—C123—H123120.4C222—C223—H223120.4
C125—C124—C123120.4 (2)C223—C224—C225120.5 (2)
C125—C124—H124119.8C223—C224—H224119.7
C123—C124—H124119.8C225—C224—H224119.7
C124—C125—C126119.3 (2)C224—C225—C226119.4 (2)
C124—C125—H125120.3C224—C225—H225120.3
C126—C125—H125120.3C226—C225—H225120.3
C125—C126—C121121.9 (2)C225—C226—C221121.7 (2)
C125—C126—H126119.1C225—C226—H226119.1
C121—C126—H126119.1C221—C226—H226119.1
C132—N131—C17A109.22 (19)C232—N231—C27A109.2 (2)
C132—N131—C131126.4 (2)C232—N231—C231126.1 (2)
C17A—N131—C131124.3 (2)C27A—N231—C231124.6 (2)
N131—C132—C133110.0 (2)N231—C232—C233110.4 (2)
N131—C132—H132125.0N231—C232—H232124.8
C133—C132—H132125.0C233—C232—H232124.8
C132—C133—C13128.4 (2)C232—C233—C23127.6 (2)
C132—C133—C13A106.2 (2)C232—C233—C23A106.1 (2)
C13—C133—C13A125.3 (2)C23—C233—C23A126.2 (2)
C134—C13A—C17A119.1 (2)C234—C23A—C27A119.1 (2)
C134—C13A—C133134.5 (2)C234—C23A—C233134.6 (2)
C17A—C13A—C133106.3 (2)C27A—C23A—C233106.3 (2)
C135—C134—C13A118.6 (2)C235—C234—C23A118.4 (2)
C135—C134—H134120.7C235—C234—H234120.8
C13A—C134—H134120.7C23A—C234—H234120.8
C134—C135—C136121.2 (2)C234—C235—C236121.4 (3)
C134—C135—H135119.4C234—C235—H235119.3
C136—C135—H135119.4C236—C235—H235119.3
C137—C136—C135121.4 (2)C237—C236—C235121.5 (2)
C137—C136—H136119.3C237—C236—H236119.3
C135—C136—H136119.3C235—C236—H236119.3
C136—C137—C17A116.9 (2)C236—C237—C27A116.7 (2)
C136—C137—H137121.5C236—C237—H237121.6
C17A—C137—H137121.5C27A—C237—H237121.6
N131—C17A—C137129.1 (2)N231—C27A—C237129.1 (2)
N131—C17A—C13A108.2 (2)N231—C27A—C23A108.0 (2)
C137—C17A—C13A122.7 (2)C237—C27A—C23A122.9 (2)
N131—C131—H13A109.5N231—C231—H23A109.5
N131—C131—H13B109.5N231—C231—H23B109.5
H13A—C131—H13B109.5H23A—C231—H23B109.5
N131—C131—H13C109.5N231—C231—H23C109.5
H13A—C131—H13C109.5H23A—C231—H23C109.5
H13B—C131—H13C109.5H23B—C231—H23C109.5
C11—C12—C13—O1339.4 (3)C21—C22—C23—O2341.5 (3)
C127—C12—C13—O1381.8 (3)C227—C22—C23—O2380.5 (3)
C11—C12—C13—C133141.1 (2)C21—C22—C23—C233139.9 (2)
C127—C12—C13—C13397.6 (3)C227—C22—C23—C23398.1 (3)
C11—C12—C127—C12158.0 (3)C21—C22—C227—C22159.6 (3)
C13—C12—C127—C121177.27 (19)C23—C22—C227—C221179.33 (19)
C12—C127—C121—C12277.7 (3)C22—C227—C221—C22280.5 (3)
C12—C127—C121—C126102.7 (3)C22—C227—C221—C22699.3 (3)
C126—C121—C122—C1230.9 (4)C226—C221—C222—C2231.8 (4)
C127—C121—C122—C123178.7 (2)C227—C221—C222—C223178.4 (2)
C126—C121—C122—Br12177.55 (19)C226—C221—C222—Br22175.73 (18)
C127—C121—C122—Br122.8 (3)C227—C221—C222—Br224.1 (3)
C121—C122—C123—C1240.7 (4)C221—C222—C223—C2242.1 (4)
Br12—C122—C123—C124177.78 (19)Br22—C222—C223—C224175.5 (2)
C122—C123—C124—C1250.0 (4)C222—C223—C224—C2250.5 (4)
C123—C124—C125—C1260.4 (4)C223—C224—C225—C2261.3 (4)
C124—C125—C126—C1210.2 (4)C224—C225—C226—C2211.6 (4)
C122—C121—C126—C1250.4 (4)C222—C221—C226—C2250.1 (4)
C127—C121—C126—C125179.2 (2)C227—C221—C226—C225179.7 (2)
C17A—N131—C132—C1330.6 (3)C27A—N231—C232—C2330.6 (3)
C131—N131—C132—C133178.6 (2)C231—N231—C232—C233177.4 (2)
N131—C132—C133—C13176.3 (2)N231—C232—C233—C23178.6 (2)
N131—C132—C133—C13A0.5 (3)N231—C232—C233—C23A0.8 (3)
O13—C13—C133—C132177.6 (3)O23—C23—C233—C232178.1 (3)
C12—C13—C133—C1322.9 (4)C22—C23—C233—C2323.3 (4)
O13—C13—C133—C13A2.6 (4)O23—C23—C233—C23A0.7 (4)
C12—C13—C133—C13A177.9 (2)C22—C23—C233—C23A179.3 (2)
C132—C133—C13A—C134177.3 (3)C232—C233—C23A—C234179.7 (3)
C13—C133—C13A—C1341.4 (5)C23—C233—C23A—C2341.9 (5)
C132—C133—C13A—C17A0.3 (3)C232—C233—C23A—C27A0.6 (3)
C13—C133—C13A—C17A176.2 (2)C23—C233—C23A—C27A178.5 (2)
C17A—C13A—C134—C1350.3 (4)C27A—C23A—C234—C2350.5 (4)
C133—C13A—C134—C135177.5 (3)C233—C23A—C234—C235180.0 (3)
C13A—C134—C135—C1361.0 (4)C23A—C234—C235—C2361.6 (4)
C134—C135—C136—C1371.0 (4)C234—C235—C236—C2371.4 (4)
C135—C136—C137—C17A0.2 (4)C235—C236—C237—C27A0.1 (4)
C132—N131—C17A—C137179.1 (3)C232—N231—C27A—C237179.3 (3)
C131—N131—C17A—C1371.1 (4)C231—N231—C27A—C2374.0 (4)
C132—N131—C17A—C13A0.4 (3)C232—N231—C27A—C23A0.2 (3)
C131—N131—C17A—C13A178.5 (2)C231—N231—C27A—C23A177.0 (2)
C136—C137—C17A—N131178.0 (2)C236—C237—C27A—N231180.0 (3)
C136—C137—C17A—C13A1.5 (4)C236—C237—C27A—C23A1.0 (4)
C134—C13A—C17A—N131178.1 (2)C234—C23A—C27A—N231180.0 (2)
C133—C13A—C17A—N1310.1 (3)C233—C23A—C27A—N2310.3 (3)
C134—C13A—C17A—C1371.5 (4)C234—C23A—C27A—C2370.9 (4)
C133—C13A—C17A—C137179.5 (2)C233—C23A—C27A—C237178.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C125—H125···O230.952.573.446 (3)153
(2RS)-3-(1-benzyl-1H-indol-3-yl)-\ 2-(2-bromobenzyl)-3-oxopropanenitrile (IIc) top
Crystal data top
C25H19BrN2OZ = 4
Mr = 443.32F(000) = 904
Triclinic, P1Dx = 1.468 Mg m3
a = 10.912 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.544 (8) ÅCell parameters from 9244 reflections
c = 15.583 (7) Åθ = 2.2–27.6°
α = 89.23 (4)°µ = 2.07 mm1
β = 79.49 (3)°T = 100 K
γ = 73.20 (3)°Plate, colourless
V = 2006.0 (18) Å30.22 × 0.21 × 0.10 mm
Data collection top
Bruker D8 Venture
diffractometer
9244 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube6872 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.112
φ and ω scansθmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1414
Tmin = 0.737, Tmax = 0.813k = 1616
96931 measured reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.025P)2 + 2.2423P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
9244 reflectionsΔρmax = 0.40 e Å3
523 parametersΔρmin = 0.57 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.5097 (2)0.73044 (17)0.58025 (14)0.0195 (5)
C110.5794 (2)0.64664 (19)0.59130 (15)0.0131 (5)
C120.6656 (2)0.53736 (18)0.60712 (15)0.0120 (5)
H120.71830.54640.65120.014*
C130.7577 (2)0.48592 (19)0.52103 (15)0.0135 (5)
O130.71866 (16)0.50668 (14)0.45193 (11)0.0195 (4)
C1270.5832 (2)0.45808 (19)0.64171 (15)0.0143 (5)
H12A0.53110.44990.59780.017*
H12B0.64270.38360.64880.017*
C1210.4926 (2)0.49869 (19)0.72782 (15)0.0142 (5)
C1220.5251 (2)0.4672 (2)0.80876 (16)0.0183 (5)
Br120.69435 (3)0.37370 (2)0.81581 (2)0.02901 (8)
C1230.4382 (3)0.5025 (2)0.88675 (17)0.0260 (6)
H1230.46200.47660.94070.031*
C1240.3165 (3)0.5757 (2)0.88513 (18)0.0265 (6)
H1240.25690.60200.93820.032*
C1250.2820 (2)0.6105 (2)0.80614 (17)0.0222 (6)
H1250.19890.66140.80490.027*
C1260.3682 (2)0.5712 (2)0.72888 (16)0.0157 (5)
H1260.34210.59430.67500.019*
N1311.05957 (19)0.31755 (16)0.58068 (13)0.0148 (4)
C1320.9391 (2)0.39054 (19)0.60079 (15)0.0154 (5)
H1320.89860.42300.65740.019*
C1330.8832 (2)0.41133 (19)0.52668 (15)0.0133 (5)
C13A0.9782 (2)0.34516 (19)0.45581 (15)0.0133 (5)
C1340.9828 (2)0.3297 (2)0.36647 (16)0.0170 (5)
H1340.91010.36580.34050.020*
C1351.0950 (2)0.2608 (2)0.31686 (17)0.0217 (6)
H1351.09970.25090.25590.026*
C1361.2021 (2)0.2051 (2)0.35422 (17)0.0224 (6)
H1361.27800.15860.31810.027*
C1371.1995 (2)0.2166 (2)0.44269 (16)0.0174 (5)
H1371.27120.17750.46860.021*
C17A1.0870 (2)0.28790 (19)0.49215 (15)0.0129 (5)
C1311.1538 (2)0.2766 (2)0.63886 (16)0.0218 (6)
H13A1.23250.30070.61780.026*
H13B1.18050.19410.63670.026*
C1411.0984 (2)0.3190 (2)0.73197 (16)0.0149 (5)
C1421.1034 (2)0.4222 (2)0.75954 (17)0.0202 (5)
H1421.14460.46510.71990.024*
C1431.0485 (2)0.4633 (2)0.84465 (17)0.0214 (6)
H1431.05010.53490.86260.026*
C1440.9916 (2)0.3996 (2)0.90330 (16)0.0179 (5)
H1440.95460.42730.96160.022*
C1450.9885 (2)0.2956 (2)0.87698 (16)0.0184 (5)
H1450.95070.25140.91740.022*
C1461.0409 (2)0.2560 (2)0.79148 (17)0.0182 (5)
H1461.03730.18510.77340.022*
N210.0140 (2)0.75831 (17)0.92059 (14)0.0192 (5)
C210.0827 (2)0.84265 (19)0.90939 (15)0.0127 (5)
C220.1675 (2)0.95153 (18)0.89134 (15)0.0119 (5)
H220.22170.94110.84860.014*
C230.2577 (2)1.00946 (18)0.97633 (15)0.0121 (5)
O230.21598 (16)0.99589 (14)1.04483 (11)0.0193 (4)
C2270.0836 (2)1.02767 (19)0.85264 (15)0.0140 (5)
H22A0.14191.10080.84090.017*
H22B0.03341.04050.89640.017*
C2210.0100 (2)0.97895 (19)0.76913 (15)0.0134 (5)
C2220.0218 (2)0.9938 (2)0.68648 (16)0.0192 (5)
Br220.19115 (3)1.08181 (2)0.67357 (2)0.03007 (8)
C2230.0658 (3)0.9457 (2)0.61163 (17)0.0278 (6)
H2230.04070.95650.55620.033*
C2240.1898 (3)0.8817 (2)0.61815 (17)0.0234 (6)
H2240.25080.84890.56710.028*
C2250.2247 (2)0.8658 (2)0.69909 (16)0.0180 (5)
H2250.30990.82170.70380.022*
C2260.1361 (2)0.9140 (2)0.77368 (16)0.0151 (5)
H2260.16170.90250.82900.018*
N2310.55993 (18)1.17202 (16)0.91369 (13)0.0137 (4)
C2320.4425 (2)1.09431 (19)0.89647 (15)0.0137 (5)
H2320.40591.05310.84260.016*
C2330.3829 (2)1.08334 (19)0.96888 (15)0.0124 (5)
C23A0.4724 (2)1.16068 (18)1.03560 (15)0.0111 (4)
C2340.4707 (2)1.1906 (2)1.12156 (15)0.0159 (5)
H2340.39781.15661.14790.019*
C2350.5773 (2)1.2708 (2)1.16723 (16)0.0191 (5)
H2350.57751.29101.22580.023*
C2360.6849 (2)1.3230 (2)1.12889 (16)0.0198 (5)
H2360.75651.37791.16190.024*
C2370.6888 (2)1.2960 (2)1.04415 (16)0.0166 (5)
H2370.76131.33161.01780.020*
C27A0.5817 (2)1.21439 (19)0.99891 (15)0.0123 (5)
C2310.6569 (2)1.2033 (2)0.85626 (16)0.0191 (5)
H23B0.69321.28540.85830.023*
H23A0.72941.17140.87790.023*
C2410.5981 (2)1.16213 (19)0.76315 (15)0.0145 (5)
C2420.5973 (2)1.0580 (2)0.73402 (17)0.0194 (5)
H2420.63641.01290.77270.023*
C2430.5399 (2)1.0189 (2)0.64900 (17)0.0204 (5)
H2430.53840.94680.63000.025*
C2440.4846 (2)1.0852 (2)0.59180 (16)0.0178 (5)
H2440.44511.05860.53360.021*
C2450.4871 (2)1.1902 (2)0.61982 (16)0.0187 (5)
H2450.45061.23630.58050.022*
C2460.5431 (2)1.22815 (19)0.70545 (16)0.0156 (5)
H2460.54371.29990.72460.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0183 (11)0.0179 (11)0.0181 (11)0.0017 (9)0.0017 (9)0.0006 (9)
C110.0118 (11)0.0158 (12)0.0105 (11)0.0041 (9)0.0015 (9)0.0027 (9)
C120.0126 (11)0.0112 (11)0.0105 (11)0.0006 (9)0.0023 (9)0.0011 (9)
C130.0137 (11)0.0124 (12)0.0145 (12)0.0041 (9)0.0025 (9)0.0017 (9)
O130.0193 (9)0.0243 (10)0.0112 (9)0.0016 (7)0.0062 (7)0.0024 (7)
C1270.0161 (12)0.0106 (11)0.0156 (12)0.0036 (9)0.0021 (9)0.0017 (9)
C1210.0170 (12)0.0143 (12)0.0141 (12)0.0093 (9)0.0020 (9)0.0003 (9)
C1220.0203 (13)0.0197 (13)0.0178 (13)0.0092 (10)0.0053 (10)0.0017 (10)
Br120.02806 (16)0.03083 (16)0.02740 (16)0.00258 (12)0.01353 (12)0.00779 (12)
C1230.0300 (15)0.0390 (17)0.0155 (13)0.0199 (13)0.0049 (11)0.0026 (12)
C1240.0236 (14)0.0372 (16)0.0196 (14)0.0165 (12)0.0068 (11)0.0091 (12)
C1250.0154 (12)0.0234 (14)0.0268 (15)0.0077 (10)0.0024 (11)0.0029 (11)
C1260.0152 (12)0.0183 (13)0.0167 (12)0.0096 (10)0.0030 (10)0.0013 (10)
N1310.0139 (10)0.0157 (10)0.0128 (10)0.0001 (8)0.0045 (8)0.0008 (8)
C1320.0157 (12)0.0165 (12)0.0116 (12)0.0011 (9)0.0015 (9)0.0021 (9)
C1330.0139 (11)0.0140 (12)0.0121 (12)0.0034 (9)0.0035 (9)0.0011 (9)
C13A0.0141 (11)0.0120 (11)0.0136 (12)0.0040 (9)0.0014 (9)0.0009 (9)
C1340.0183 (12)0.0171 (12)0.0157 (12)0.0046 (10)0.0046 (10)0.0000 (10)
C1350.0236 (13)0.0268 (14)0.0124 (12)0.0052 (11)0.0007 (10)0.0071 (10)
C1360.0175 (13)0.0242 (14)0.0207 (14)0.0023 (10)0.0035 (10)0.0080 (11)
C1370.0125 (12)0.0172 (13)0.0197 (13)0.0015 (9)0.0004 (10)0.0019 (10)
C17A0.0144 (11)0.0107 (11)0.0136 (12)0.0043 (9)0.0016 (9)0.0011 (9)
C1310.0140 (12)0.0283 (15)0.0174 (13)0.0042 (10)0.0056 (10)0.0003 (11)
C1410.0114 (11)0.0170 (12)0.0147 (12)0.0007 (9)0.0063 (9)0.0015 (9)
C1420.0191 (13)0.0200 (13)0.0237 (14)0.0076 (10)0.0075 (11)0.0099 (11)
C1430.0244 (14)0.0154 (13)0.0259 (15)0.0064 (10)0.0074 (11)0.0007 (10)
C1440.0182 (12)0.0206 (13)0.0152 (13)0.0043 (10)0.0056 (10)0.0014 (10)
C1450.0215 (13)0.0219 (13)0.0154 (13)0.0104 (10)0.0067 (10)0.0060 (10)
C1460.0212 (13)0.0141 (12)0.0223 (14)0.0059 (10)0.0106 (10)0.0011 (10)
N210.0190 (11)0.0189 (11)0.0163 (11)0.0018 (9)0.0010 (9)0.0026 (9)
C210.0127 (11)0.0154 (12)0.0094 (11)0.0040 (9)0.0001 (9)0.0024 (9)
C220.0125 (11)0.0125 (11)0.0094 (11)0.0007 (9)0.0033 (9)0.0003 (9)
C230.0152 (11)0.0117 (11)0.0096 (11)0.0040 (9)0.0028 (9)0.0002 (9)
O230.0185 (9)0.0236 (10)0.0123 (9)0.0013 (7)0.0062 (7)0.0025 (7)
C2270.0144 (11)0.0115 (11)0.0148 (12)0.0017 (9)0.0029 (9)0.0005 (9)
C2210.0145 (11)0.0119 (11)0.0146 (12)0.0064 (9)0.0010 (9)0.0010 (9)
C2220.0164 (12)0.0184 (13)0.0192 (13)0.0010 (10)0.0044 (10)0.0031 (10)
Br220.02352 (15)0.03471 (17)0.02276 (16)0.00809 (11)0.00826 (11)0.00540 (12)
C2230.0295 (15)0.0362 (16)0.0118 (13)0.0010 (12)0.0029 (11)0.0038 (11)
C2240.0208 (13)0.0263 (14)0.0171 (13)0.0025 (11)0.0048 (10)0.0002 (11)
C2250.0122 (11)0.0198 (13)0.0209 (13)0.0043 (9)0.0008 (10)0.0015 (10)
C2260.0147 (12)0.0179 (12)0.0149 (12)0.0078 (9)0.0034 (9)0.0019 (9)
N2310.0111 (9)0.0161 (10)0.0120 (10)0.0002 (8)0.0030 (8)0.0018 (8)
C2320.0132 (11)0.0141 (12)0.0117 (12)0.0006 (9)0.0026 (9)0.0015 (9)
C2330.0146 (11)0.0112 (11)0.0107 (11)0.0027 (9)0.0023 (9)0.0008 (9)
C23A0.0128 (11)0.0100 (11)0.0101 (11)0.0037 (9)0.0007 (9)0.0000 (9)
C2340.0155 (12)0.0175 (12)0.0147 (12)0.0042 (9)0.0038 (9)0.0001 (10)
C2350.0233 (13)0.0222 (13)0.0115 (12)0.0079 (10)0.0002 (10)0.0059 (10)
C2360.0178 (12)0.0191 (13)0.0187 (13)0.0027 (10)0.0023 (10)0.0043 (10)
C2370.0123 (11)0.0162 (12)0.0200 (13)0.0032 (9)0.0015 (10)0.0007 (10)
C27A0.0136 (11)0.0124 (11)0.0108 (11)0.0050 (9)0.0000 (9)0.0008 (9)
C2310.0156 (12)0.0252 (14)0.0145 (13)0.0000 (10)0.0073 (10)0.0006 (10)
C2410.0135 (12)0.0164 (12)0.0133 (12)0.0011 (9)0.0070 (9)0.0022 (9)
C2420.0223 (13)0.0186 (13)0.0195 (13)0.0067 (10)0.0085 (11)0.0076 (10)
C2430.0253 (14)0.0148 (12)0.0247 (14)0.0073 (10)0.0107 (11)0.0007 (10)
C2440.0188 (12)0.0197 (13)0.0150 (12)0.0042 (10)0.0058 (10)0.0023 (10)
C2450.0225 (13)0.0194 (13)0.0174 (13)0.0096 (10)0.0066 (10)0.0028 (10)
C2460.0213 (12)0.0109 (11)0.0166 (13)0.0043 (9)0.0091 (10)0.0008 (9)
Geometric parameters (Å, º) top
N11—C111.137 (3)N21—C211.139 (3)
C11—C121.468 (3)C21—C221.468 (3)
C12—C131.544 (3)C22—C231.545 (3)
C12—C1271.554 (3)C22—C2271.551 (3)
C12—H121.0000C22—H221.0000
C13—O131.227 (3)C23—O231.226 (3)
C13—C1331.435 (3)C23—C2331.436 (3)
C127—C1211.510 (3)C227—C2211.511 (3)
C127—H12A0.9900C227—H22A0.9900
C127—H12B0.9900C227—H22B0.9900
C121—C1221.393 (3)C221—C2221.391 (3)
C121—C1261.396 (3)C221—C2261.396 (3)
C122—C1231.387 (4)C222—C2231.385 (4)
C122—Br121.902 (3)C222—Br221.903 (2)
C123—C1241.384 (4)C223—C2241.381 (4)
C123—H1230.9500C223—H2230.9500
C124—C1251.381 (4)C224—C2251.378 (4)
C124—H1240.9500C224—H2240.9500
C125—C1261.383 (3)C225—C2261.387 (3)
C125—H1250.9500C225—H2250.9500
C126—H1260.9500C226—H2260.9500
N131—C1321.351 (3)N231—C2321.351 (3)
N131—C17A1.389 (3)N231—C27A1.390 (3)
N131—C1311.472 (3)N231—C2311.473 (3)
C132—C1331.390 (3)C232—C2331.388 (3)
C132—H1320.9500C232—H2320.9500
C133—C13A1.447 (3)C233—C23A1.444 (3)
C13A—C1341.398 (3)C23A—C2341.401 (3)
C13A—C17A1.409 (3)C23A—C27A1.406 (3)
C134—C1351.381 (3)C234—C2351.382 (3)
C134—H1340.9500C234—H2340.9500
C135—C1361.398 (4)C235—C2361.402 (4)
C135—H1350.9500C235—H2350.9500
C136—C1371.382 (4)C236—C2371.379 (3)
C136—H1360.9500C236—H2360.9500
C137—C17A1.393 (3)C237—C27A1.392 (3)
C137—H1370.9500C237—H2370.9500
C131—C1411.506 (3)C231—C2411.507 (3)
C131—H13A0.9900C231—H23B0.9900
C131—H13B0.9900C231—H23A0.9900
C141—C1421.389 (4)C241—C2421.385 (3)
C141—C1461.390 (4)C241—C2461.388 (3)
C142—C1431.391 (4)C242—C2431.388 (4)
C142—H1420.9500C242—H2420.9500
C143—C1441.385 (4)C243—C2441.387 (4)
C143—H1430.9500C243—H2430.9500
C144—C1451.384 (4)C244—C2451.384 (3)
C144—H1440.9500C244—H2440.9500
C145—C1461.387 (4)C245—C2461.390 (3)
C145—H1450.9500C245—H2450.9500
C146—H1460.9500C246—H2460.9500
N11—C11—C12178.1 (3)N21—C21—C22177.5 (3)
C11—C12—C13109.69 (19)C21—C22—C23110.56 (19)
C11—C12—C127109.87 (19)C21—C22—C227109.81 (19)
C13—C12—C127108.84 (18)C23—C22—C227108.10 (19)
C11—C12—H12109.5C21—C22—H22109.4
C13—C12—H12109.5C23—C22—H22109.4
C127—C12—H12109.5C227—C22—H22109.4
O13—C13—C133123.3 (2)O23—C23—C233123.7 (2)
O13—C13—C12118.9 (2)O23—C23—C22118.8 (2)
C133—C13—C12117.8 (2)C233—C23—C22117.35 (19)
C121—C127—C12113.25 (19)C221—C227—C22112.96 (19)
C121—C127—H12A108.9C221—C227—H22A109.0
C12—C127—H12A108.9C22—C227—H22A109.0
C121—C127—H12B108.9C221—C227—H22B109.0
C12—C127—H12B108.9C22—C227—H22B109.0
H12A—C127—H12B107.7H22A—C227—H22B107.8
C122—C121—C126116.5 (2)C222—C221—C226116.9 (2)
C122—C121—C127123.7 (2)C222—C221—C227124.0 (2)
C126—C121—C127119.8 (2)C226—C221—C227119.1 (2)
C123—C122—C121122.5 (2)C223—C222—C221122.2 (2)
C123—C122—Br12117.2 (2)C223—C222—Br22117.78 (19)
C121—C122—Br12120.30 (19)C221—C222—Br22120.00 (18)
C124—C123—C122119.3 (3)C224—C223—C222119.6 (2)
C124—C123—H123120.4C224—C223—H223120.2
C122—C123—H123120.4C222—C223—H223120.2
C125—C124—C123119.8 (2)C225—C224—C223119.7 (2)
C125—C124—H124120.1C225—C224—H224120.2
C123—C124—H124120.1C223—C224—H224120.2
C124—C125—C126120.1 (2)C224—C225—C226120.3 (2)
C124—C125—H125119.9C224—C225—H225119.8
C126—C125—H125119.9C226—C225—H225119.8
C125—C126—C121121.8 (2)C225—C226—C221121.3 (2)
C125—C126—H126119.1C225—C226—H226119.3
C121—C126—H126119.1C221—C226—H226119.3
C132—N131—C17A109.16 (19)C232—N231—C27A109.04 (19)
C132—N131—C131127.8 (2)C232—N231—C231127.2 (2)
C17A—N131—C131122.94 (19)C27A—N231—C231123.64 (19)
N131—C132—C133110.2 (2)N231—C232—C233110.2 (2)
N131—C132—H132124.9N231—C232—H232124.9
C133—C132—H132124.9C233—C232—H232124.9
C132—C133—C13126.9 (2)C232—C233—C23127.0 (2)
C132—C133—C13A106.3 (2)C232—C233—C23A106.3 (2)
C13—C133—C13A126.8 (2)C23—C233—C23A126.8 (2)
C134—C13A—C17A118.9 (2)C234—C23A—C27A118.7 (2)
C134—C13A—C133134.8 (2)C234—C23A—C233134.8 (2)
C17A—C13A—C133106.4 (2)C27A—C23A—C233106.5 (2)
C135—C134—C13A118.6 (2)C235—C234—C23A118.7 (2)
C135—C134—H134120.7C235—C234—H234120.7
C13A—C134—H134120.7C23A—C234—H234120.7
C134—C135—C136121.6 (2)C234—C235—C236121.4 (2)
C134—C135—H135119.2C234—C235—H235119.3
C136—C135—H135119.2C236—C235—H235119.3
C137—C136—C135121.2 (2)C237—C236—C235121.3 (2)
C137—C136—H136119.4C237—C236—H236119.4
C135—C136—H136119.4C235—C236—H236119.4
C136—C137—C17A116.9 (2)C236—C237—C27A117.0 (2)
C136—C137—H137121.5C236—C237—H237121.5
C17A—C137—H137121.5C27A—C237—H237121.5
N131—C17A—C137129.2 (2)N231—C27A—C237129.0 (2)
N131—C17A—C13A108.0 (2)N231—C27A—C23A107.97 (19)
C137—C17A—C13A122.8 (2)C237—C27A—C23A123.0 (2)
N131—C131—C141112.18 (19)N231—C231—C241111.72 (19)
N131—C131—H13A109.2N231—C231—H23B109.3
C141—C131—H13A109.2C241—C231—H23B109.3
N131—C131—H13B109.2N231—C231—H23A109.3
C141—C131—H13B109.2C241—C231—H23A109.3
H13A—C131—H13B107.9H23B—C231—H23A107.9
C142—C141—C146118.9 (2)C242—C241—C246119.0 (2)
C142—C141—C131120.3 (2)C242—C241—C231120.8 (2)
C146—C141—C131120.7 (2)C246—C241—C231120.2 (2)
C141—C142—C143120.5 (2)C241—C242—C243120.7 (2)
C141—C142—H142119.7C241—C242—H242119.6
C143—C142—H142119.7C243—C242—H242119.6
C144—C143—C142119.9 (2)C244—C243—C242119.9 (2)
C144—C143—H143120.1C244—C243—H243120.1
C142—C143—H143120.1C242—C243—H243120.1
C145—C144—C143120.0 (2)C245—C244—C243119.8 (2)
C145—C144—H144120.0C245—C244—H244120.1
C143—C144—H144120.0C243—C244—H244120.1
C144—C145—C146119.9 (2)C244—C245—C246120.0 (2)
C144—C145—H145120.1C244—C245—H245120.0
C146—C145—H145120.1C246—C245—H245120.0
C145—C146—C141120.7 (2)C241—C246—C245120.5 (2)
C145—C146—H146119.6C241—C246—H246119.7
C141—C146—H146119.6C245—C246—H246119.7
C11—C12—C13—O1331.9 (3)C21—C22—C23—O2334.5 (3)
C127—C12—C13—O1388.3 (3)C227—C22—C23—O2385.7 (3)
C11—C12—C13—C133151.1 (2)C21—C22—C23—C233150.1 (2)
C127—C12—C13—C13388.6 (2)C227—C22—C23—C23389.7 (2)
C11—C12—C127—C12161.9 (3)C21—C22—C227—C22158.8 (3)
C13—C12—C127—C121177.96 (19)C23—C22—C227—C221179.53 (18)
C12—C127—C121—C12293.1 (3)C22—C227—C221—C22287.4 (3)
C12—C127—C121—C12687.4 (3)C22—C227—C221—C22692.0 (3)
C126—C121—C122—C1232.0 (4)C226—C221—C222—C2230.9 (4)
C127—C121—C122—C123177.5 (2)C227—C221—C222—C223178.5 (2)
C126—C121—C122—Br12177.34 (17)C226—C221—C222—Br22179.65 (18)
C127—C121—C122—Br123.1 (3)C227—C221—C222—Br220.9 (3)
C121—C122—C123—C1243.0 (4)C221—C222—C223—C2240.9 (4)
Br12—C122—C123—C124176.3 (2)Br22—C222—C223—C224179.7 (2)
C122—C123—C124—C1251.6 (4)C222—C223—C224—C2250.5 (4)
C123—C124—C125—C1260.7 (4)C223—C224—C225—C2260.2 (4)
C124—C125—C126—C1211.8 (4)C224—C225—C226—C2210.2 (4)
C122—C121—C126—C1250.4 (3)C222—C221—C226—C2250.6 (3)
C127—C121—C126—C125179.9 (2)C227—C221—C226—C225178.9 (2)
C17A—N131—C132—C1330.1 (3)C27A—N231—C232—C2330.4 (3)
C131—N131—C132—C133177.4 (2)C231—N231—C232—C233175.8 (2)
N131—C132—C133—C13178.4 (2)N231—C232—C233—C23180.0 (2)
N131—C132—C133—C13A0.1 (3)N231—C232—C233—C23A0.3 (3)
O13—C13—C133—C132174.1 (2)O23—C23—C233—C232172.6 (2)
C12—C13—C133—C1329.1 (4)C22—C23—C233—C23212.3 (4)
O13—C13—C133—C13A3.9 (4)O23—C23—C233—C23A7.0 (4)
C12—C13—C133—C13A172.9 (2)C22—C23—C233—C23A168.1 (2)
C132—C133—C13A—C134179.2 (3)C232—C233—C23A—C234179.3 (3)
C13—C133—C13A—C1340.9 (4)C23—C233—C23A—C2341.1 (4)
C132—C133—C13A—C17A0.0 (3)C232—C233—C23A—C27A0.1 (3)
C13—C133—C13A—C17A178.4 (2)C23—C233—C23A—C27A179.8 (2)
C17A—C13A—C134—C1351.5 (4)C27A—C23A—C234—C2350.8 (3)
C133—C13A—C134—C135177.7 (3)C233—C23A—C234—C235179.9 (3)
C13A—C134—C135—C1361.3 (4)C23A—C234—C235—C2360.8 (4)
C134—C135—C136—C1370.3 (4)C234—C235—C236—C2370.2 (4)
C135—C136—C137—C17A1.5 (4)C235—C236—C237—C27A0.5 (4)
C132—N131—C17A—C137179.0 (2)C232—N231—C27A—C237179.6 (2)
C131—N131—C17A—C1371.5 (4)C231—N231—C27A—C2374.8 (4)
C132—N131—C17A—C13A0.1 (3)C232—N231—C27A—C23A0.3 (3)
C131—N131—C17A—C13A177.6 (2)C231—N231—C27A—C23A176.0 (2)
C136—C137—C17A—N131177.7 (2)C236—C237—C27A—N231179.7 (2)
C136—C137—C17A—C13A1.2 (4)C236—C237—C27A—C23A0.5 (4)
C134—C13A—C17A—N131179.4 (2)C234—C23A—C27A—N231179.2 (2)
C133—C13A—C17A—N1310.1 (3)C233—C23A—C27A—N2310.1 (3)
C134—C13A—C17A—C1370.3 (4)C234—C23A—C27A—C2370.1 (4)
C133—C13A—C17A—C137179.1 (2)C233—C23A—C27A—C237179.4 (2)
C132—N131—C131—C1414.5 (4)C232—N231—C231—C24116.2 (3)
C17A—N131—C131—C141178.5 (2)C27A—N231—C231—C241169.0 (2)
N131—C131—C141—C14285.5 (3)N231—C231—C241—C24289.9 (3)
N131—C131—C141—C14694.2 (3)N231—C231—C241—C24689.6 (3)
C146—C141—C142—C1431.8 (3)C246—C241—C242—C2431.4 (3)
C131—C141—C142—C143177.9 (2)C231—C241—C242—C243178.2 (2)
C141—C142—C143—C1441.8 (4)C241—C242—C243—C2441.1 (4)
C142—C143—C144—C1450.4 (4)C242—C243—C244—C2450.1 (4)
C143—C144—C145—C1461.0 (4)C243—C244—C245—C2461.0 (4)
C144—C145—C146—C1411.0 (4)C242—C241—C246—C2450.4 (3)
C142—C141—C146—C1450.4 (3)C231—C241—C246—C245179.1 (2)
C131—C141—C146—C145179.3 (2)C244—C245—C246—C2410.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C225—H225···N110.952.623.304 (4)129
C231—H23A···O23i0.992.573.415 (4)143
Symmetry code: (i) x1, y+2, z+2.
(E)-1-(1-Acetyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl acetate (III) top
Crystal data top
C22H17BrN2O3F(000) = 1776
Mr = 437.28Dx = 1.523 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.406 (9) ÅCell parameters from 4412 reflections
b = 8.773 (4) Åθ = 2.5–27.6°
c = 23.028 (9) ŵ = 2.18 mm1
β = 103.318 (15)°T = 173 K
V = 3815 (3) Å3Block, colourless
Z = 80.42 × 0.32 × 0.24 mm
Data collection top
Bruker D8 Venture
diffractometer
4379 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3435 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.057
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2525
Tmin = 0.420, Tmax = 0.594k = 1111
49228 measured reflectionsl = 2929
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.136 w = 1/[σ2(Fo2) + (0.0427P)2 + 18.903P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4379 reflectionsΔρmax = 0.80 e Å3
255 parametersΔρmin = 1.89 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.62414 (17)0.3935 (4)0.29701 (16)0.0337 (8)
C20.62775 (17)0.4887 (4)0.34346 (16)0.0379 (8)
C30.65936 (19)0.4495 (5)0.40750 (16)0.0428 (10)
H3A0.66660.33780.41070.051*
H3B0.62500.47710.43160.051*
O110.64160 (14)0.2417 (3)0.31041 (10)0.0376 (6)
C110.6943 (2)0.1770 (4)0.28804 (15)0.0372 (8)
O120.73268 (15)0.2507 (3)0.26607 (14)0.0533 (8)
C1110.6960 (3)0.0090 (4)0.29636 (17)0.0619 (14)
H11A0.71450.03920.26470.093*
H11B0.64800.02840.29460.093*
H11C0.72660.01630.33530.093*
N110.57308 (15)0.5602 (3)0.14756 (14)0.0386 (7)
C120.60600 (18)0.5633 (4)0.20784 (16)0.0374 (8)
H120.63100.64830.22800.045*
C130.59756 (16)0.4290 (4)0.23388 (16)0.0325 (7)
C13A0.55771 (16)0.3298 (4)0.18758 (16)0.0359 (8)
C140.53385 (19)0.1801 (5)0.18688 (18)0.0452 (10)
H140.54390.11970.22210.054*
C150.4948 (2)0.1214 (5)0.1331 (2)0.0531 (12)
H150.47660.02060.13210.064*
C160.48178 (18)0.2070 (5)0.08106 (19)0.0474 (11)
H160.45620.16210.04490.057*
C170.50493 (16)0.3554 (5)0.08029 (18)0.0408 (9)
H170.49580.41400.04460.049*
C17A0.54247 (16)0.4151 (4)0.13455 (17)0.0373 (8)
C180.5663 (2)0.6840 (4)0.10827 (19)0.0518 (11)
O180.52769 (17)0.6757 (3)0.05891 (13)0.0612 (9)
C190.6093 (3)0.8218 (5)0.1310 (2)0.083 (2)
H19A0.60470.89700.09880.125*
H19B0.65920.79270.14490.125*
H19C0.59230.86620.16420.125*
C210.59703 (18)0.6371 (5)0.33325 (19)0.0472 (10)
N210.57241 (18)0.7561 (5)0.32946 (19)0.0635 (12)
C310.72899 (17)0.5274 (4)0.43386 (15)0.0318 (7)
C320.75899 (19)0.5183 (4)0.49450 (16)0.0363 (8)
Br320.71124 (3)0.40569 (5)0.54420 (2)0.06003 (18)
C330.82242 (19)0.5875 (4)0.52081 (19)0.0450 (9)
H330.84130.57910.56260.054*
C340.85800 (19)0.6691 (5)0.4856 (2)0.0520 (12)
H340.90160.71770.50300.062*
C350.82997 (19)0.6798 (5)0.4250 (2)0.0478 (11)
H350.85470.73530.40070.057*
C360.76622 (17)0.6105 (4)0.39925 (17)0.0357 (8)
H360.74750.61940.35750.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0289 (16)0.0368 (18)0.0431 (18)0.0134 (14)0.0244 (14)0.0193 (15)
C20.0262 (16)0.046 (2)0.049 (2)0.0179 (15)0.0247 (15)0.0261 (17)
C30.042 (2)0.054 (2)0.0413 (19)0.0323 (17)0.0287 (16)0.0278 (17)
O110.0553 (15)0.0328 (12)0.0344 (12)0.0188 (11)0.0304 (11)0.0129 (10)
C110.063 (2)0.0254 (16)0.0305 (16)0.0017 (15)0.0254 (16)0.0015 (13)
O120.0598 (17)0.0359 (14)0.080 (2)0.0198 (13)0.0487 (16)0.0268 (14)
C1110.135 (5)0.0218 (17)0.0329 (19)0.010 (2)0.028 (2)0.0060 (14)
N110.0341 (15)0.0296 (14)0.0467 (17)0.0119 (12)0.0017 (13)0.0189 (13)
C120.0333 (17)0.0328 (17)0.0437 (19)0.0079 (14)0.0034 (15)0.0211 (15)
C130.0243 (15)0.0335 (17)0.0435 (18)0.0025 (13)0.0158 (14)0.0209 (14)
C13A0.0199 (15)0.0441 (19)0.049 (2)0.0058 (13)0.0203 (14)0.0261 (16)
C140.0328 (18)0.056 (2)0.056 (2)0.0243 (17)0.0307 (17)0.0271 (19)
C150.038 (2)0.064 (3)0.067 (3)0.0304 (19)0.033 (2)0.036 (2)
C160.0216 (16)0.065 (3)0.060 (2)0.0111 (16)0.0176 (16)0.036 (2)
C170.0166 (14)0.050 (2)0.055 (2)0.0042 (14)0.0073 (14)0.0285 (18)
C17A0.0171 (14)0.0426 (19)0.053 (2)0.0052 (13)0.0102 (14)0.0257 (17)
C180.061 (3)0.0333 (19)0.050 (2)0.0215 (18)0.010 (2)0.0204 (17)
O180.070 (2)0.0474 (17)0.0525 (17)0.0266 (15)0.0145 (15)0.0224 (14)
C190.134 (5)0.0234 (19)0.064 (3)0.011 (2)0.035 (3)0.0124 (19)
C210.0237 (16)0.061 (2)0.061 (2)0.0117 (17)0.0190 (16)0.042 (2)
N210.0372 (18)0.066 (2)0.090 (3)0.0017 (17)0.0200 (18)0.051 (2)
C310.0292 (16)0.0276 (15)0.0457 (19)0.0128 (13)0.0235 (14)0.0206 (14)
C320.0383 (18)0.0296 (17)0.047 (2)0.0078 (14)0.0212 (16)0.0194 (15)
Br320.0965 (4)0.0472 (3)0.0470 (2)0.0271 (2)0.0384 (2)0.01872 (18)
C330.0353 (19)0.046 (2)0.055 (2)0.0015 (16)0.0134 (17)0.0282 (18)
C340.0247 (17)0.060 (3)0.076 (3)0.0150 (17)0.0211 (18)0.042 (2)
C350.0351 (19)0.048 (2)0.072 (3)0.0234 (16)0.0369 (19)0.031 (2)
C360.0312 (17)0.0341 (17)0.050 (2)0.0160 (14)0.0267 (15)0.0218 (15)
Geometric parameters (Å, º) top
C1—C21.346 (4)C15—C161.388 (7)
C1—O111.391 (4)C15—H150.9500
C1—C131.460 (5)C16—C171.378 (6)
C2—C211.429 (6)C16—H160.9500
C2—C31.501 (6)C17—C17A1.395 (5)
C3—C311.511 (4)C17—H170.9500
C3—H3A0.9900C18—O181.211 (5)
C3—H3B0.9900C18—C191.494 (6)
O11—C111.369 (4)C19—H19A0.9800
C11—O121.185 (4)C19—H19B0.9800
C11—C1111.486 (5)C19—H19C0.9800
C111—H11A0.9800C21—N211.143 (6)
C111—H11B0.9800C31—C321.386 (5)
C111—H11C0.9800C31—C361.398 (4)
N11—C121.388 (5)C32—C331.381 (5)
N11—C181.400 (5)C32—Br321.906 (4)
N11—C17A1.407 (4)C33—C341.381 (6)
C12—C131.349 (5)C33—H330.9500
C12—H120.9500C34—C351.378 (6)
C13—C13A1.453 (4)C34—H340.9500
C13A—C141.392 (5)C35—C361.383 (5)
C13A—C17A1.404 (6)C35—H350.9500
C14—C151.393 (5)C36—H360.9500
C14—H140.9500
C2—C1—O11116.9 (3)C14—C15—H15119.3
C2—C1—C13126.9 (3)C17—C16—C15121.8 (4)
O11—C1—C13115.9 (3)C17—C16—H16119.1
C1—C2—C21119.4 (4)C15—C16—H16119.1
C1—C2—C3125.0 (4)C16—C17—C17A116.6 (4)
C21—C2—C3115.5 (3)C16—C17—H17121.7
C2—C3—C31114.6 (3)C17A—C17—H17121.7
C2—C3—H3A108.6C17—C17A—C13A122.7 (4)
C31—C3—H3A108.6C17—C17A—N11129.6 (4)
C2—C3—H3B108.6C13A—C17A—N11107.6 (3)
C31—C3—H3B108.6O18—C18—N11120.4 (4)
H3A—C3—H3B107.6O18—C18—C19123.5 (4)
C11—O11—C1118.6 (2)N11—C18—C19116.1 (3)
O12—C11—O11122.1 (3)C18—C19—H19A109.5
O12—C11—C111126.8 (4)C18—C19—H19B109.5
O11—C11—C111111.1 (3)H19A—C19—H19B109.5
C11—C111—H11A109.5C18—C19—H19C109.5
C11—C111—H11B109.5H19A—C19—H19C109.5
H11A—C111—H11B109.5H19B—C19—H19C109.5
C11—C111—H11C109.5N21—C21—C2174.9 (5)
H11A—C111—H11C109.5C32—C31—C36116.9 (3)
H11B—C111—H11C109.5C32—C31—C3120.5 (3)
C12—N11—C18125.7 (3)C36—C31—C3122.6 (3)
C12—N11—C17A107.8 (3)C33—C32—C31122.8 (3)
C18—N11—C17A126.3 (3)C33—C32—Br32118.1 (3)
C13—C12—N11110.6 (3)C31—C32—Br32119.0 (2)
C13—C12—H12124.7C32—C33—C34119.1 (4)
N11—C12—H12124.7C32—C33—H33120.5
C12—C13—C13A107.2 (3)C34—C33—H33120.5
C12—C13—C1125.3 (3)C35—C34—C33119.7 (3)
C13A—C13—C1127.5 (3)C35—C34—H34120.1
C14—C13A—C17A119.3 (3)C33—C34—H34120.1
C14—C13A—C13133.9 (4)C34—C35—C36120.6 (4)
C17A—C13A—C13106.8 (3)C34—C35—H35119.7
C13A—C14—C15118.1 (4)C36—C35—H35119.7
C13A—C14—H14121.0C35—C36—C31120.9 (4)
C15—C14—H14121.0C35—C36—H36119.6
C16—C15—C14121.4 (4)C31—C36—H36119.6
C16—C15—H15119.3
O11—C1—C2—C21167.3 (3)C16—C17—C17A—C13A1.2 (4)
C13—C1—C2—C216.6 (5)C16—C17—C17A—N11179.2 (3)
O11—C1—C2—C39.8 (5)C14—C13A—C17A—C171.0 (5)
C13—C1—C2—C3176.3 (3)C13—C13A—C17A—C17179.5 (3)
C1—C2—C3—C31108.7 (4)C14—C13A—C17A—N11179.4 (3)
C21—C2—C3—C3174.1 (4)C13—C13A—C17A—N111.2 (3)
C2—C1—O11—C11123.6 (3)C12—N11—C17A—C17178.7 (3)
C13—C1—O11—C1161.9 (4)C18—N11—C17A—C176.6 (6)
C1—O11—C11—O1212.3 (5)C12—N11—C17A—C13A0.5 (3)
C1—O11—C11—C111168.6 (3)C18—N11—C17A—C13A175.2 (3)
C18—N11—C12—C13174.3 (3)C12—N11—C18—O18168.9 (4)
C17A—N11—C12—C130.5 (4)C17A—N11—C18—O184.9 (6)
N11—C12—C13—C13A1.2 (4)C12—N11—C18—C1911.6 (6)
N11—C12—C13—C1178.8 (3)C17A—N11—C18—C19174.6 (4)
C2—C1—C13—C1236.4 (5)C2—C3—C31—C32171.0 (3)
O11—C1—C13—C12149.7 (3)C2—C3—C31—C369.3 (5)
C2—C1—C13—C13A143.5 (3)C36—C31—C32—C330.3 (5)
O11—C1—C13—C13A30.3 (4)C3—C31—C32—C33179.9 (3)
C12—C13—C13A—C14179.2 (3)C36—C31—C32—Br32179.6 (2)
C1—C13—C13A—C140.8 (6)C3—C31—C32—Br320.2 (4)
C12—C13—C13A—C17A1.4 (3)C31—C32—C33—C340.2 (5)
C1—C13—C13A—C17A178.5 (3)Br32—C32—C33—C34179.7 (3)
C17A—C13A—C14—C150.7 (5)C32—C33—C34—C350.2 (6)
C13—C13A—C14—C15178.6 (3)C33—C34—C35—C360.5 (6)
C13A—C14—C15—C162.2 (5)C34—C35—C36—C310.4 (6)
C14—C15—C16—C172.0 (6)C32—C31—C36—C350.0 (5)
C15—C16—C17—C17A0.3 (5)C3—C31—C36—C35179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O180.952.382.904 (5)114
C17—H17···O18i0.952.453.133 (5)129
C35—H35···Cg2ii0.952.763.582 (5)146
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y+1/2, z+1/2.
(E)-1-(1-Benzyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl benzoate (IV) top
Crystal data top
C32H23BrN2O2F(000) = 1120
Mr = 547.42Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.886 (4) ÅCell parameters from 7902 reflections
b = 8.129 (3) Åθ = 2.7–31.7°
c = 21.432 (6) ŵ = 1.67 mm1
β = 104.638 (12)°T = 100 K
V = 2509.3 (14) Å3Block, colourless
Z = 40.21 × 0.12 × 0.12 mm
Data collection top
Bruker D8 Venture
diffractometer
6999 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube5828 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.074
φ and ω scansθmax = 29.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2020
Tmin = 0.676, Tmax = 0.818k = 1011
87392 measured reflectionsl = 2929
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0363P)2 + 2.1078P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
6999 reflectionsΔρmax = 0.46 e Å3
334 parametersΔρmin = 0.94 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.25289 (10)0.82801 (18)0.47696 (7)0.0105 (3)
C20.27542 (10)0.93568 (19)0.52616 (7)0.0106 (3)
C30.20854 (11)1.04297 (19)0.55102 (7)0.0124 (3)
H3A0.22651.15990.54940.015*
H3B0.14501.02940.52290.015*
O110.15866 (7)0.80355 (14)0.44880 (5)0.0130 (2)
C110.13009 (11)0.83794 (18)0.38406 (7)0.0127 (3)
O120.17813 (8)0.91169 (15)0.35614 (6)0.0191 (2)
C1110.03599 (11)0.7745 (2)0.35434 (8)0.0142 (3)
C1120.00318 (12)0.8198 (2)0.29061 (8)0.0183 (3)
H1120.02850.89390.26930.022*
C1130.08877 (12)0.7562 (2)0.25838 (9)0.0239 (4)
H1130.11550.78560.21470.029*
C1140.13509 (12)0.6503 (2)0.28971 (10)0.0272 (4)
H1140.19340.60610.26730.033*
C1150.09723 (12)0.6078 (2)0.35362 (10)0.0258 (4)
H1150.13000.53600.37500.031*
C1160.01135 (11)0.6703 (2)0.38637 (9)0.0190 (3)
H1160.01470.64200.43020.023*
N110.44244 (9)0.61866 (17)0.42862 (6)0.0104 (2)
C120.40480 (10)0.75381 (19)0.45008 (7)0.0114 (3)
H120.43570.85600.46100.014*
C130.31527 (10)0.72040 (19)0.45362 (7)0.0105 (3)
C13A0.29651 (10)0.55208 (19)0.43271 (7)0.0098 (3)
C140.22226 (10)0.4437 (2)0.42943 (7)0.0127 (3)
H140.16650.48050.43880.015*
C150.23190 (11)0.2821 (2)0.41223 (8)0.0147 (3)
H150.18200.20760.40990.018*
C160.31388 (11)0.2253 (2)0.39810 (7)0.0147 (3)
H160.31830.11340.38650.018*
C170.38813 (11)0.32977 (19)0.40090 (7)0.0128 (3)
H170.44370.29210.39160.015*
C17A0.37781 (10)0.49289 (19)0.41803 (7)0.0100 (3)
C210.37140 (11)0.95045 (19)0.55964 (7)0.0116 (3)
N210.44759 (9)0.96982 (18)0.58749 (7)0.0165 (3)
C310.20907 (11)0.99745 (19)0.61958 (7)0.0127 (3)
C320.14347 (11)0.8950 (2)0.63576 (8)0.0159 (3)
Br320.03898 (2)0.81786 (2)0.57128 (2)0.02400 (6)
C330.14907 (13)0.8471 (2)0.69864 (9)0.0223 (4)
H330.10340.77630.70800.027*
C340.22217 (14)0.9037 (2)0.74773 (8)0.0253 (4)
H340.22750.87030.79100.030*
C350.28693 (13)1.0083 (2)0.73362 (8)0.0225 (4)
H350.33641.04850.76730.027*
C360.28043 (11)1.0552 (2)0.67051 (8)0.0179 (3)
H360.32541.12830.66160.022*
C180.54006 (10)0.5994 (2)0.42926 (7)0.0119 (3)
H18A0.56520.50350.45650.014*
H18B0.57430.69800.44960.014*
C1810.55868 (10)0.57590 (19)0.36390 (7)0.0105 (3)
C1820.63057 (11)0.4722 (2)0.35846 (8)0.0160 (3)
H1820.66510.41420.39520.019*
C1830.65196 (12)0.4533 (2)0.29938 (9)0.0217 (4)
H1830.70110.38220.29580.026*
C1840.60197 (13)0.5376 (2)0.24594 (8)0.0216 (4)
H1840.61690.52490.20560.026*
C1850.53023 (12)0.6405 (2)0.25104 (8)0.0207 (3)
H1850.49570.69800.21420.025*
C1860.50856 (11)0.6599 (2)0.30995 (8)0.0154 (3)
H1860.45930.73090.31330.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0080 (6)0.0117 (7)0.0113 (6)0.0008 (5)0.0017 (5)0.0019 (5)
C20.0106 (6)0.0112 (7)0.0101 (6)0.0008 (5)0.0028 (5)0.0012 (5)
C30.0134 (7)0.0125 (7)0.0116 (7)0.0021 (6)0.0036 (5)0.0000 (5)
O110.0076 (5)0.0175 (6)0.0133 (5)0.0005 (4)0.0012 (4)0.0021 (4)
C110.0131 (7)0.0091 (7)0.0139 (7)0.0009 (5)0.0005 (5)0.0016 (5)
O120.0185 (6)0.0183 (6)0.0176 (6)0.0046 (5)0.0007 (5)0.0040 (5)
C1110.0104 (7)0.0122 (7)0.0180 (7)0.0022 (5)0.0004 (6)0.0049 (6)
C1120.0153 (7)0.0199 (8)0.0175 (8)0.0036 (6)0.0002 (6)0.0054 (6)
C1130.0159 (8)0.0299 (10)0.0214 (8)0.0049 (7)0.0037 (6)0.0098 (7)
C1140.0110 (8)0.0288 (10)0.0365 (11)0.0003 (7)0.0034 (7)0.0127 (8)
C1150.0132 (8)0.0226 (9)0.0398 (11)0.0030 (7)0.0032 (7)0.0025 (8)
C1160.0119 (7)0.0182 (8)0.0253 (8)0.0008 (6)0.0019 (6)0.0012 (7)
N110.0086 (6)0.0133 (6)0.0100 (6)0.0008 (5)0.0034 (4)0.0013 (5)
C120.0125 (7)0.0117 (7)0.0108 (6)0.0008 (5)0.0043 (5)0.0004 (5)
C130.0095 (6)0.0124 (7)0.0095 (6)0.0010 (5)0.0020 (5)0.0003 (5)
C13A0.0111 (6)0.0116 (7)0.0061 (6)0.0005 (5)0.0009 (5)0.0003 (5)
C140.0109 (7)0.0157 (7)0.0113 (6)0.0009 (6)0.0027 (5)0.0000 (6)
C150.0160 (7)0.0139 (7)0.0142 (7)0.0038 (6)0.0037 (6)0.0003 (6)
C160.0200 (8)0.0114 (7)0.0129 (7)0.0010 (6)0.0043 (6)0.0012 (6)
C170.0151 (7)0.0135 (7)0.0103 (6)0.0024 (6)0.0040 (5)0.0005 (5)
C17A0.0116 (6)0.0126 (7)0.0056 (6)0.0003 (5)0.0019 (5)0.0007 (5)
C210.0144 (7)0.0098 (7)0.0116 (7)0.0004 (5)0.0053 (5)0.0012 (5)
N210.0135 (6)0.0194 (7)0.0164 (6)0.0005 (5)0.0031 (5)0.0039 (5)
C310.0124 (7)0.0136 (7)0.0126 (7)0.0041 (6)0.0041 (5)0.0010 (6)
C320.0151 (7)0.0165 (8)0.0172 (7)0.0029 (6)0.0059 (6)0.0003 (6)
Br320.01663 (9)0.02752 (10)0.02782 (10)0.00654 (7)0.00557 (7)0.00047 (7)
C330.0272 (9)0.0222 (9)0.0222 (8)0.0060 (7)0.0152 (7)0.0040 (7)
C340.0354 (10)0.0293 (10)0.0134 (8)0.0150 (8)0.0105 (7)0.0036 (7)
C350.0233 (9)0.0296 (10)0.0132 (7)0.0114 (7)0.0019 (6)0.0042 (7)
C360.0145 (7)0.0227 (8)0.0165 (7)0.0037 (6)0.0035 (6)0.0051 (6)
C180.0083 (6)0.0179 (8)0.0094 (6)0.0009 (5)0.0020 (5)0.0005 (5)
C1810.0090 (6)0.0123 (7)0.0104 (6)0.0024 (5)0.0029 (5)0.0014 (5)
C1820.0136 (7)0.0167 (8)0.0187 (7)0.0022 (6)0.0061 (6)0.0018 (6)
C1830.0200 (8)0.0218 (9)0.0283 (9)0.0004 (7)0.0154 (7)0.0041 (7)
C1840.0249 (9)0.0283 (9)0.0158 (7)0.0097 (7)0.0129 (7)0.0066 (7)
C1850.0201 (8)0.0305 (9)0.0116 (7)0.0042 (7)0.0041 (6)0.0027 (7)
C1860.0122 (7)0.0212 (8)0.0128 (7)0.0016 (6)0.0032 (6)0.0018 (6)
Geometric parameters (Å, º) top
C1—C21.346 (2)C15—C161.408 (2)
C1—O111.3942 (18)C15—H150.9500
C1—C131.453 (2)C16—C171.383 (2)
C2—C211.433 (2)C16—H160.9500
C2—C31.518 (2)C17—C17A1.395 (2)
C3—C311.513 (2)C17—H170.9500
C3—H3A0.9900C21—N211.151 (2)
C3—H3B0.9900C31—C321.392 (2)
O11—C111.3734 (19)C31—C361.398 (2)
C11—O121.202 (2)C32—C331.385 (2)
C11—C1111.477 (2)C32—Br321.9068 (17)
C111—C1161.389 (2)C33—C341.387 (3)
C111—C1121.393 (2)C33—H330.9500
C112—C1131.387 (2)C34—C351.375 (3)
C112—H1120.9500C34—H340.9500
C113—C1141.379 (3)C35—C361.385 (2)
C113—H1130.9500C35—H350.9500
C114—C1151.387 (3)C36—H360.9500
C114—H1140.9500C18—C1811.507 (2)
C115—C1161.390 (2)C18—H18A0.9900
C115—H1150.9500C18—H18B0.9900
C116—H1160.9500C181—C1861.387 (2)
N11—C121.365 (2)C181—C1821.390 (2)
N11—C17A1.383 (2)C182—C1831.390 (2)
N11—C181.4581 (19)C182—H1820.9500
C12—C131.381 (2)C183—C1841.380 (3)
C12—H120.9500C183—H1830.9500
C13—C13A1.445 (2)C184—C1851.382 (3)
C13A—C141.401 (2)C184—H1840.9500
C13A—C17A1.410 (2)C185—C1861.389 (2)
C14—C151.381 (2)C185—H1850.9500
C14—H140.9500C186—H1860.9500
C2—C1—O11117.13 (13)C17—C16—C15121.04 (15)
C2—C1—C13127.35 (14)C17—C16—H16119.5
O11—C1—C13115.19 (13)C15—C16—H16119.5
C1—C2—C21117.79 (14)C16—C17—C17A117.09 (14)
C1—C2—C3126.37 (14)C16—C17—H17121.5
C21—C2—C3115.83 (13)C17A—C17—H17121.5
C31—C3—C2110.94 (12)N11—C17A—C17128.89 (14)
C31—C3—H3A109.5N11—C17A—C13A108.18 (13)
C2—C3—H3A109.5C17—C17A—C13A122.75 (14)
C31—C3—H3B109.5N21—C21—C2176.67 (17)
C2—C3—H3B109.5C32—C31—C36116.67 (15)
H3A—C3—H3B108.0C32—C31—C3123.79 (14)
C11—O11—C1115.40 (12)C36—C31—C3119.50 (15)
O12—C11—O11122.22 (14)C33—C32—C31122.49 (16)
O12—C11—C111125.31 (15)C33—C32—Br32116.75 (13)
O11—C11—C111112.47 (14)C31—C32—Br32120.75 (12)
C116—C111—C112120.47 (15)C32—C33—C34119.17 (17)
C116—C111—C11122.96 (15)C32—C33—H33120.4
C112—C111—C11116.54 (15)C34—C33—H33120.4
C113—C112—C111119.61 (18)C35—C34—C33119.83 (16)
C113—C112—H112120.2C35—C34—H34120.1
C111—C112—H112120.2C33—C34—H34120.1
C114—C113—C112119.99 (18)C34—C35—C36120.35 (17)
C114—C113—H113120.0C34—C35—H35119.8
C112—C113—H113120.0C36—C35—H35119.8
C113—C114—C115120.54 (17)C35—C36—C31121.45 (17)
C113—C114—H114119.7C35—C36—H36119.3
C115—C114—H114119.7C31—C36—H36119.3
C114—C115—C116120.01 (18)N11—C18—C181114.95 (12)
C114—C115—H115120.0N11—C18—H18A108.5
C116—C115—H115120.0C181—C18—H18A108.5
C111—C116—C115119.35 (17)N11—C18—H18B108.5
C111—C116—H116120.3C181—C18—H18B108.5
C115—C116—H116120.3H18A—C18—H18B107.5
C12—N11—C17A108.82 (12)C186—C181—C182119.47 (14)
C12—N11—C18125.19 (13)C186—C181—C18121.72 (14)
C17A—N11—C18124.93 (13)C182—C181—C18118.76 (14)
N11—C12—C13110.14 (14)C181—C182—C183120.12 (15)
N11—C12—H12124.9C181—C182—H182119.9
C13—C12—H12124.9C183—C182—H182119.9
C12—C13—C13A106.43 (13)C184—C183—C182120.09 (16)
C12—C13—C1127.59 (14)C184—C183—H183120.0
C13A—C13—C1125.90 (13)C182—C183—H183120.0
C14—C13A—C17A119.00 (14)C183—C184—C185120.01 (15)
C14—C13A—C13134.36 (14)C183—C184—H184120.0
C17A—C13A—C13106.43 (13)C185—C184—H184120.0
C15—C14—C13A118.52 (14)C184—C185—C186120.15 (16)
C15—C14—H14120.7C184—C185—H185119.9
C13A—C14—H14120.7C186—C185—H185119.9
C14—C15—C16121.59 (15)C181—C186—C185120.15 (15)
C14—C15—H15119.2C181—C186—H186119.9
C16—C15—H15119.2C185—C186—H186119.9
O11—C1—C2—C21174.10 (13)C14—C15—C16—C170.1 (2)
C13—C1—C2—C211.0 (2)C15—C16—C17—C17A0.2 (2)
O11—C1—C2—C34.8 (2)C12—N11—C17A—C17174.54 (14)
C13—C1—C2—C3177.92 (14)C18—N11—C17A—C175.8 (2)
C1—C2—C3—C31115.94 (17)C12—N11—C17A—C13A0.67 (16)
C21—C2—C3—C3163.03 (17)C18—N11—C17A—C13A169.37 (13)
C2—C1—O11—C11121.15 (15)C16—C17—C17A—N11175.16 (15)
C13—C1—O11—C1164.94 (17)C16—C17—C17A—C13A0.6 (2)
C1—O11—C11—O1213.0 (2)C14—C13A—C17A—N11176.22 (13)
C1—O11—C11—C111166.92 (12)C13—C13A—C17A—N110.69 (16)
O12—C11—C111—C116170.58 (16)C14—C13A—C17A—C170.7 (2)
O11—C11—C111—C1169.4 (2)C13—C13A—C17A—C17174.88 (14)
O12—C11—C111—C1127.3 (2)C2—C3—C31—C3298.04 (18)
O11—C11—C111—C112172.79 (14)C2—C3—C31—C3679.71 (18)
C116—C111—C112—C1132.0 (2)C36—C31—C32—C332.0 (2)
C11—C111—C112—C113175.86 (15)C3—C31—C32—C33175.78 (15)
C111—C112—C113—C1140.8 (3)C36—C31—C32—Br32176.51 (12)
C112—C113—C114—C1150.6 (3)C3—C31—C32—Br325.7 (2)
C113—C114—C115—C1160.9 (3)C31—C32—C33—C340.5 (3)
C112—C111—C116—C1151.8 (2)Br32—C32—C33—C34178.09 (13)
C11—C111—C116—C115175.96 (16)C32—C33—C34—C351.1 (3)
C114—C115—C116—C1110.4 (3)C33—C34—C35—C361.1 (3)
C17A—N11—C12—C130.38 (17)C34—C35—C36—C310.5 (3)
C18—N11—C12—C13169.05 (13)C32—C31—C36—C352.0 (2)
N11—C12—C13—C13A0.05 (17)C3—C31—C36—C35175.87 (15)
N11—C12—C13—C1176.84 (14)C12—N11—C18—C181119.05 (16)
C2—C1—C13—C1236.3 (3)C17A—N11—C18—C18174.06 (19)
O11—C1—C13—C12150.51 (15)N11—C18—C181—C18638.1 (2)
C2—C1—C13—C13A140.01 (16)N11—C18—C181—C182144.58 (15)
O11—C1—C13—C13A33.2 (2)C186—C181—C182—C1830.1 (2)
C12—C13—C13A—C14174.99 (16)C18—C181—C182—C183177.33 (15)
C1—C13—C13A—C142.0 (3)C181—C182—C183—C1840.1 (3)
C12—C13—C13A—C17A0.45 (16)C182—C183—C184—C1850.3 (3)
C1—C13—C13A—C17A176.50 (14)C183—C184—C185—C1860.3 (3)
C17A—C13A—C14—C150.4 (2)C182—C181—C186—C1850.1 (2)
C13—C13A—C14—C15173.65 (16)C18—C181—C186—C185177.27 (15)
C13A—C14—C15—C160.0 (2)C184—C185—C186—C1810.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C36—H36···Cg3i0.952.923.739 (2)145
C183—H183···Cg1ii0.952.973.807 (2)148
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+1.
2-Benzoyl-3-(2-bromophenyl)acrylonitrile (V) top
Crystal data top
C16H10BrNOF(000) = 624
Mr = 312.15Dx = 1.604 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.986 (4) ÅCell parameters from 2986 reflections
b = 8.977 (4) Åθ = 2.3–27.6°
c = 13.209 (5) ŵ = 3.17 mm1
β = 97.140 (17)°T = 100 K
V = 1292.6 (9) Å3Block, orange
Z = 40.27 × 0.26 × 0.23 mm
Data collection top
Bruker D8 Venture
diffractometer
2985 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube2754 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.036
φ and ω scansθmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1414
Tmin = 0.366, Tmax = 0.482k = 1111
30048 measured reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.023P)2 + 0.9733P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
2985 reflectionsΔρmax = 0.34 e Å3
172 parametersΔρmin = 0.52 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.52114 (14)0.09372 (17)0.66805 (12)0.0114 (3)
N10.46836 (14)0.03411 (16)0.72541 (11)0.0179 (3)
C20.59444 (13)0.16873 (17)0.60003 (11)0.0092 (3)
C30.58208 (13)0.31481 (17)0.57997 (11)0.0087 (3)
H30.63620.35690.53690.010*
C270.67937 (14)0.06881 (17)0.55029 (11)0.0096 (3)
O270.65240 (11)0.06180 (13)0.53670 (9)0.0158 (2)
C210.79280 (14)0.13384 (16)0.51742 (11)0.0098 (3)
C220.83791 (15)0.07181 (18)0.43254 (12)0.0132 (3)
H220.79560.00830.39670.016*
C230.94443 (16)0.1274 (2)0.40076 (13)0.0176 (3)
H230.97460.08620.34250.021*
C241.00734 (15)0.2433 (2)0.45368 (13)0.0190 (3)
H241.08040.28110.43160.023*
C250.96375 (15)0.30402 (19)0.53877 (13)0.0158 (3)
H251.00720.38280.57510.019*
C260.85669 (14)0.24971 (17)0.57080 (11)0.0115 (3)
H260.82680.29140.62910.014*
C310.49311 (14)0.41605 (16)0.61805 (11)0.0091 (3)
C320.53014 (14)0.55567 (17)0.65733 (11)0.0102 (3)
Br320.69900 (2)0.60654 (2)0.67042 (2)0.01496 (6)
C330.44831 (15)0.65635 (18)0.69096 (12)0.0140 (3)
H330.47560.75100.71680.017*
C340.32568 (15)0.61617 (19)0.68605 (12)0.0155 (3)
H340.26840.68360.70910.019*
C350.28618 (14)0.47790 (19)0.64766 (12)0.0152 (3)
H350.20220.45100.64500.018*
C360.36892 (14)0.37893 (17)0.61324 (12)0.0122 (3)
H360.34100.28520.58620.015*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0104 (7)0.0090 (7)0.0152 (7)0.0003 (5)0.0025 (6)0.0013 (6)
N10.0202 (7)0.0143 (7)0.0210 (7)0.0010 (6)0.0093 (6)0.0022 (6)
C20.0079 (6)0.0104 (7)0.0095 (6)0.0018 (5)0.0017 (5)0.0012 (5)
C30.0077 (6)0.0113 (7)0.0071 (6)0.0017 (5)0.0014 (5)0.0019 (5)
C270.0108 (7)0.0103 (7)0.0076 (6)0.0010 (5)0.0001 (5)0.0002 (5)
O270.0186 (6)0.0097 (5)0.0197 (6)0.0017 (4)0.0047 (5)0.0031 (4)
C210.0091 (7)0.0105 (7)0.0097 (7)0.0024 (5)0.0015 (5)0.0017 (5)
C220.0152 (7)0.0135 (7)0.0111 (7)0.0037 (6)0.0024 (6)0.0001 (6)
C230.0183 (8)0.0240 (9)0.0121 (7)0.0060 (7)0.0073 (6)0.0017 (6)
C240.0121 (7)0.0270 (9)0.0192 (8)0.0003 (7)0.0068 (6)0.0063 (7)
C250.0118 (7)0.0181 (8)0.0174 (8)0.0028 (6)0.0012 (6)0.0005 (6)
C260.0115 (7)0.0128 (7)0.0103 (7)0.0011 (6)0.0019 (5)0.0005 (6)
C310.0106 (7)0.0099 (7)0.0069 (6)0.0013 (5)0.0019 (5)0.0013 (5)
C320.0111 (7)0.0115 (7)0.0081 (6)0.0004 (5)0.0010 (5)0.0014 (5)
Br320.01375 (9)0.01610 (9)0.01532 (9)0.00647 (6)0.00294 (6)0.00398 (6)
C330.0215 (8)0.0103 (7)0.0105 (7)0.0024 (6)0.0028 (6)0.0003 (6)
C340.0172 (8)0.0185 (8)0.0113 (7)0.0102 (6)0.0038 (6)0.0021 (6)
C350.0097 (7)0.0224 (8)0.0139 (7)0.0025 (6)0.0023 (6)0.0018 (6)
C360.0113 (7)0.0141 (7)0.0113 (7)0.0007 (6)0.0016 (6)0.0004 (6)
Geometric parameters (Å, º) top
C1—N11.143 (2)C24—H240.9500
C1—C21.445 (2)C25—C261.387 (2)
C2—C31.341 (2)C25—H250.9500
C2—C271.503 (2)C26—H260.9500
C3—C311.469 (2)C31—C321.398 (2)
C3—H30.9500C31—C361.398 (2)
C27—O271.217 (2)C32—C331.386 (2)
C27—C211.489 (2)C32—Br321.8973 (17)
C21—C261.396 (2)C33—C341.388 (2)
C21—C221.397 (2)C33—H330.9500
C22—C231.385 (2)C34—C351.390 (2)
C22—H220.9500C34—H340.9500
C23—C241.389 (3)C35—C361.387 (2)
C23—H230.9500C35—H350.9500
C24—C251.387 (2)C36—H360.9500
N1—C1—C2176.52 (17)C24—C25—H25120.0
C3—C2—C1121.85 (14)C26—C25—H25120.0
C3—C2—C27123.38 (13)C25—C26—C21120.01 (15)
C1—C2—C27114.70 (13)C25—C26—H26120.0
C2—C3—C31126.35 (14)C21—C26—H26120.0
C2—C3—H3116.8C32—C31—C36117.91 (14)
C31—C3—H3116.8C32—C31—C3120.45 (14)
O27—C27—C21122.14 (14)C36—C31—C3121.61 (14)
O27—C27—C2119.10 (14)C33—C32—C31122.22 (15)
C21—C27—C2118.75 (13)C33—C32—Br32118.65 (12)
C26—C21—C22119.75 (14)C31—C32—Br32119.07 (11)
C26—C21—C27122.10 (14)C32—C33—C34118.67 (15)
C22—C21—C27118.10 (14)C32—C33—H33120.7
C23—C22—C21119.81 (15)C34—C33—H33120.7
C23—C22—H22120.1C33—C34—C35120.42 (15)
C21—C22—H22120.1C33—C34—H34119.8
C22—C23—C24120.27 (15)C35—C34—H34119.8
C22—C23—H23119.9C36—C35—C34120.26 (15)
C24—C23—H23119.9C36—C35—H35119.9
C25—C24—C23120.14 (15)C34—C35—H35119.9
C25—C24—H24119.9C35—C36—C31120.52 (15)
C23—C24—H24119.9C35—C36—H36119.7
C24—C25—C26120.02 (16)C31—C36—H36119.7
C1—C2—C3—C312.8 (2)C22—C21—C26—C250.8 (2)
C27—C2—C3—C31173.86 (14)C27—C21—C26—C25178.30 (14)
C3—C2—C27—O27149.43 (15)C2—C3—C31—C32134.36 (16)
C1—C2—C27—O2727.4 (2)C2—C3—C31—C3647.8 (2)
C3—C2—C27—C2129.4 (2)C36—C31—C32—C330.0 (2)
C1—C2—C27—C21153.71 (14)C3—C31—C32—C33177.87 (14)
O27—C27—C21—C26147.87 (15)C36—C31—C32—Br32177.34 (11)
C2—C27—C21—C2633.3 (2)C3—C31—C32—Br324.77 (19)
O27—C27—C21—C2229.7 (2)C31—C32—C33—C340.5 (2)
C2—C27—C21—C22149.12 (14)Br32—C32—C33—C34176.85 (11)
C26—C21—C22—C231.2 (2)C32—C33—C34—C350.3 (2)
C27—C21—C22—C23178.82 (14)C33—C34—C35—C360.4 (2)
C21—C22—C23—C240.8 (2)C34—C35—C36—C310.9 (2)
C22—C23—C24—C250.0 (3)C32—C31—C36—C350.7 (2)
C23—C24—C25—C260.4 (3)C3—C31—C36—C35178.56 (14)
C24—C25—C26—C210.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···N1i0.952.553.425 (3)154
C36—H36···O27ii0.952.593.459 (2)153
C3—H3···Cg1iii0.952.733.431 (2)131
C23—H23···Cg1iv0.952.693.506 (2)144
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1; (iii) x+1, y+1, z+1; (iv) x+1/2, y+1/2, z1/2.
Selected torsion angles (°) top
(Indolyl)C—C—C—C(N)aO—C—C—C(N)b(NC)C—C—C—C(Br)c
(Ib)-29.8 (2)152.77 (14)147.66 (16)
(IIb), x = 1141.1 (2)-39.4 (3)-77.7 (3)
(IIb), x = 2-139.9 (2)41.5 (3)50.5 (3)
(IIc), x = 1151.1 (2)-31.9 (3)-93.1 (3)
(IIc), x = 2-150.1 (2)34.5 (3)97.4 (3)
(III)6.6 (5)-167.3 (3)171.0 (3)
(IV)1.0 (2)174.10 (13)-98.04 (10)
(V)-153.71 (14)27.4 (2)134.3 (16)
Notes: (a) In (Ib), C23—C28—C2—C1; in (IIb) and (IIc), Cx33Cx34—Cx2—Cx1 (x = 1 or 2); in (III) and (IV), C13—C1—C2—C21; in (V), C21—C27—C2—C1. (b) In (Ib), O28—C28—C2—C1; in (IIb) and (IIc), Ox23—Cx3—Cx2—Cx1 (x = 1 or 2); in (III) and (IV), O11—C1—C2—C21; in (V), O27—C27—C2—C1. (b) In (Ib) and (V), C2—C3—C31—C32; in (IIb) and (IIc), Cx2—Cx27—Cx21—Cx22 (x = 1 or 2); in (III) and (IV), C2—C3—C31—C32.
Hydrogen bonds and short intra- and intermolecular contacts (Å, °) top
CompoundD—H···AD—HH···AD···AD—H···A
(Ib)C24—H24···Cg1i0.952.773.544 (3)139
(IIb)C125—H125···O230.952.573.446 (3)153
(IIc)C225—H225···N110.952.623.304 (4)129
C231—H23A···O23ii0.952.573.415 (4)143
(III)C17—H17···O18iii0.952.453.133 (5)129
C35—H35···Cg2iv0.952.763.582 (5)146
(IV)C36—H36···Cg3v0.952.923.739 (2)146
C183—H183···Cg1vi0.952.972.807 (2)148
(V)C33—H33···N1i0.952.553.425 (3)154
C36—H36···O27vii0.952.593.459 (2)153
C3—H3···Cg1vi0.952.733.431 (2)131
C23—H23···Cg1viii0.952.693.506 (2)144
Cg1, Cg2 and Cg3 represent the centroids of the C31–C36, C13A/C14–C17/C17A and C181–C196 rings, respectively.

Symmetry codes: (i) x, y+1, z; (ii) -x-1, -y+2, -z+2; (iii) -x+1, -y+1, -z; (iv) -x+3/2, y+1/2, -z+1/2; (v) -x+1, -y+2, -z+1; (vi) -x+1, -y+1, -z+1; (vii) -x+1, -y, -z+1; (viii) x+1/2, -y+1/2, z-1/2.
 

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