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The reactions of two 3-(2-allyl­anilino)-3-phenyl­acrylate esters with acetic anhydride and with strong acids has revealed a richly diverse reactivity pro­viding a number of unexpected products. Thus, acetyl­ation of ethyl 3-(2-allyl­anilino)-3-phenyl­acrylate, (Ia), or ethyl 3-(2-allyl-4-methyl­anilino)-3-phenyl­acrylate, (Ib), with acetic anhydride yields not only the expected acetyl­ated esters, (II), as the major products but also the unexpected polysubstituted quinolines 3-acetyl-8-allyl-2-phenyl­quinolin-4-yl acetate, (IIIa), and 3-acetyl-8-allyl-6-methyl-2-phenyl­quinolin-4-yl acetate, (IIIb), as minor products. Subsequent reaction of the major product ethyl 2-[(2-allyl-4-methyl­anilino)(phen­yl)methyl­idene]-3-oxo­butano­ate, (IIb), with concentrated sulfuric acid did not provide the expected 3-acetyl­quinoline derivative, but instead two unexpected products, namely ethyl 4-ethyl-2-phenyl-1,4-di­hydro­quinoline-3-carboxyl­ate, (IV), and ethyl 3-acetyl-4-ethyl-2-phenyl-3,4-di­hydro­quinoline-3-carboxyl­ate, (V), in yields of 39 and 22%, respectively. The reaction of (Ib) with Eaton's reagent gave both the quinoline (Z)-6-methyl-2-phenyl-8-(prop-1-en-1-yl)quino­lin-4(1H)-one, (VI), and the unexpected tricyclic product (2RS)-2,8-dimethyl-4-phenyl-1,2-di­hydro-6H-pyrrolo­[3,2,1-ij]quinolin-6-one, (VII), in yields of 71 and 12%, respectively. The products (II)-(VII) have all been fully characterized spectroscopically and the crystal structures of two of the unexpected products, i.e. (IIIb) (C23H21NO3) and (VII) (C19H17NO), are reported here. The formation of compounds (IV), (V) and (VII) all require an isomerization of the initial allyl substituent, with migration of the C=C double bond from the terminal site to the inter­nal site. In (IIIb), the two acetyl substituents are oriented such that the intra­molecular distance between the two carbonyl O atoms is only 3.243 (2) Å, and in (VII), the five-membered ring adopts a twisted half-chair conformation. The mol­ecules of compound (IIIb) are linked by two independent hydrogen bonds to form sheets built from R43(20) rings and the sheets are linked by a [pi]-[pi] stacking inter­action to form a three-dimensional framework structure. The mol­ecules of compound (VII) are linked by a single type of C-H...O hydrogen bond to form centrosymmetric R22(14) dimers. The mol­ecules of compound (V), which crystallizes with Z' = 2, are linked by two N-H...O and two C-H...O hydrogen bonds, forming a chain of rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616011062/yf3108sup1.cif
Contains datablocks global, IIIb, VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011062/yf3108IIIbsup2.hkl
Contains datablock IIIb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011062/yf3108VIIsup3.hkl
Contains datablock VII

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616011062/yf3108IIIbsup4.cml
Supplementary material

CCDC references: 1491446; 1491445

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

(IIIb) 3-Acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate top
Crystal data top
C23H21NO3F(000) = 760
Mr = 359.41Dx = 1.290 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.0386 (9) ÅCell parameters from 4245 reflections
b = 8.2036 (8) Åθ = 3.0–27.5°
c = 25.119 (3) ŵ = 0.09 mm1
β = 96.385 (10)°T = 120 K
V = 1851.0 (3) Å3Plate, colourless
Z = 40.25 × 0.20 × 0.12 mm
Data collection top
Bruker D8 Venture
diffractometer
4239 independent reflections
Radiation source: high brilliance microfocus sealed tube2459 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.085
φ and ω scansθmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1111
Tmin = 0.816, Tmax = 0.990k = 1010
27579 measured reflectionsl = 3231
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.9869P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4239 reflectionsΔρmax = 0.22 e Å3
247 parametersΔρmin = 0.23 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
N10.19551 (18)0.4041 (2)0.43813 (7)0.0192 (4)
C20.1631 (2)0.4066 (3)0.38799 (8)0.0186 (5)
C30.0312 (2)0.3342 (3)0.37123 (8)0.0198 (5)
C40.0654 (2)0.2610 (3)0.41013 (8)0.0195 (5)
C4A0.0340 (2)0.2511 (3)0.46368 (8)0.0199 (5)
C50.1278 (2)0.1716 (3)0.50443 (8)0.0214 (5)
H50.21620.12020.49580.026*
C60.0936 (2)0.1676 (3)0.55606 (8)0.0207 (5)
C70.0385 (2)0.2466 (3)0.56815 (9)0.0217 (5)
H70.06150.24540.60410.026*
C80.1348 (2)0.3247 (3)0.53011 (8)0.0195 (5)
C8A0.0998 (2)0.3271 (3)0.47597 (8)0.0183 (5)
C210.2708 (2)0.4959 (3)0.34951 (8)0.0209 (5)
C220.2245 (2)0.6021 (3)0.31125 (8)0.0232 (5)
H220.12110.61620.30890.028*
C230.3268 (2)0.6871 (3)0.27672 (9)0.0280 (5)
H230.29340.75990.25120.034*
C240.4772 (3)0.6664 (3)0.27935 (9)0.0309 (6)
H240.54730.72360.25530.037*
C250.5261 (2)0.5617 (3)0.31717 (9)0.0301 (6)
H250.62970.54760.31900.036*
C260.4241 (2)0.4778 (3)0.35234 (9)0.0244 (5)
H260.45820.40760.37850.029*
C310.0016 (2)0.3358 (3)0.31348 (8)0.0228 (5)
O310.11676 (17)0.3967 (2)0.30221 (6)0.0297 (4)
C320.1067 (3)0.2543 (3)0.27240 (9)0.0287 (5)
H32A0.11310.31610.23880.043*
H32B0.20500.25040.28530.043*
H32C0.07290.14320.26620.043*
O410.20487 (15)0.20056 (19)0.40043 (6)0.0235 (4)
C410.2151 (3)0.0768 (3)0.36407 (8)0.0229 (5)
O420.10873 (17)0.01788 (19)0.33862 (6)0.0287 (4)
C420.3742 (2)0.0296 (3)0.36258 (9)0.0317 (6)
H42A0.40900.03180.39510.048*
H42B0.43490.12800.36070.048*
H42C0.38310.03840.33100.048*
C610.1954 (2)0.0834 (3)0.59909 (9)0.0266 (5)
H61A0.22510.02280.58590.040*
H61B0.14320.06780.63090.040*
H61C0.28420.15060.60850.040*
C810.2728 (2)0.4104 (3)0.54514 (8)0.0224 (5)
H81A0.26170.42580.58450.027*
H81B0.27720.52010.52860.027*
C820.4189 (2)0.3262 (3)0.52922 (8)0.0249 (5)
H820.50410.37020.54300.030*
C830.4399 (3)0.1981 (3)0.49821 (10)0.0325 (6)
H83A0.35810.14970.48350.039*
H83B0.53690.15360.49050.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0185 (9)0.0177 (9)0.0215 (9)0.0021 (8)0.0026 (7)0.0019 (8)
C20.0156 (10)0.0172 (11)0.0234 (11)0.0051 (9)0.0043 (9)0.0009 (9)
C30.0180 (11)0.0199 (11)0.0221 (11)0.0025 (9)0.0049 (9)0.0033 (10)
C40.0147 (10)0.0201 (11)0.0240 (11)0.0008 (9)0.0030 (9)0.0049 (9)
C4A0.0200 (11)0.0171 (11)0.0227 (11)0.0034 (9)0.0024 (9)0.0036 (9)
C50.0154 (10)0.0211 (12)0.0279 (12)0.0023 (9)0.0029 (9)0.0027 (10)
C60.0187 (11)0.0202 (12)0.0225 (11)0.0030 (9)0.0015 (9)0.0011 (10)
C70.0228 (11)0.0202 (11)0.0224 (11)0.0057 (10)0.0041 (9)0.0011 (9)
C80.0170 (10)0.0191 (11)0.0226 (11)0.0039 (9)0.0029 (9)0.0031 (9)
C8A0.0181 (10)0.0153 (11)0.0211 (11)0.0039 (9)0.0009 (9)0.0025 (9)
C210.0195 (10)0.0237 (12)0.0200 (11)0.0001 (10)0.0039 (9)0.0056 (10)
C220.0186 (11)0.0273 (13)0.0240 (11)0.0000 (10)0.0041 (9)0.0020 (10)
C230.0294 (13)0.0318 (13)0.0237 (12)0.0042 (11)0.0066 (10)0.0030 (11)
C240.0268 (12)0.0413 (15)0.0235 (12)0.0085 (11)0.0017 (10)0.0001 (11)
C250.0164 (11)0.0424 (15)0.0311 (13)0.0013 (10)0.0010 (10)0.0046 (12)
C260.0223 (11)0.0269 (13)0.0244 (12)0.0014 (10)0.0047 (9)0.0025 (10)
C310.0213 (11)0.0220 (12)0.0259 (12)0.0071 (10)0.0057 (9)0.0007 (10)
O310.0231 (8)0.0351 (10)0.0325 (9)0.0014 (8)0.0097 (7)0.0044 (8)
C320.0309 (13)0.0324 (14)0.0226 (12)0.0041 (11)0.0027 (10)0.0026 (10)
O410.0174 (7)0.0270 (9)0.0267 (8)0.0034 (7)0.0045 (6)0.0046 (7)
C410.0290 (12)0.0222 (12)0.0181 (11)0.0042 (10)0.0052 (10)0.0026 (10)
O420.0316 (9)0.0264 (9)0.0278 (8)0.0002 (8)0.0026 (7)0.0034 (7)
C420.0303 (13)0.0363 (15)0.0300 (13)0.0085 (12)0.0097 (10)0.0008 (11)
C610.0247 (12)0.0283 (13)0.0265 (12)0.0012 (10)0.0008 (10)0.0016 (10)
C810.0222 (11)0.0253 (12)0.0202 (11)0.0002 (10)0.0046 (9)0.0007 (10)
C820.0205 (11)0.0282 (13)0.0267 (12)0.0001 (10)0.0063 (9)0.0047 (11)
C830.0223 (12)0.0307 (14)0.0455 (15)0.0050 (11)0.0081 (11)0.0006 (12)
Geometric parameters (Å, º) top
N1—C21.325 (3)C24—H240.9500
N1—C8A1.366 (3)C25—C261.387 (3)
C2—C31.437 (3)C25—H250.9500
C2—C211.487 (3)C26—H260.9500
C3—C41.374 (3)C31—O311.216 (2)
C3—C311.512 (3)C31—C321.498 (3)
C4—O411.401 (2)C32—H32A0.9800
C4—C4A1.408 (3)C32—H32B0.9800
C4A—C51.414 (3)C32—H32C0.9800
C4A—C8A1.425 (3)O41—C411.376 (3)
C5—C61.367 (3)C41—O421.195 (3)
C5—H50.9500C41—C421.494 (3)
C6—C71.421 (3)C42—H42A0.9800
C6—C611.507 (3)C42—H42B0.9800
C7—C81.377 (3)C42—H42C0.9800
C7—H70.9500C61—H61A0.9800
C8—C8A1.430 (3)C61—H61B0.9800
C8—C811.516 (3)C61—H61C0.9800
C21—C221.395 (3)C81—C821.504 (3)
C21—C261.403 (3)C81—H81A0.9900
C22—C231.384 (3)C81—H81B0.9900
C22—H220.9500C82—C831.309 (3)
C23—C241.379 (3)C82—H820.9500
C23—H230.9500C83—H83A0.9500
C24—C251.389 (3)C83—H83B0.9500
C2—N1—C8A118.61 (18)C24—C25—H25119.9
N1—C2—C3123.42 (19)C25—C26—C21120.3 (2)
N1—C2—C21115.32 (18)C25—C26—H26119.8
C3—C2—C21121.22 (18)C21—C26—H26119.8
C4—C3—C2117.03 (18)O31—C31—C32122.26 (19)
C4—C3—C31120.64 (18)O31—C31—C3119.4 (2)
C2—C3—C31122.33 (19)C32—C31—C3118.30 (18)
C3—C4—O41122.93 (18)C31—C32—H32A109.5
C3—C4—C4A121.71 (19)C31—C32—H32B109.5
O41—C4—C4A115.24 (18)H32A—C32—H32B109.5
C4—C4A—C5123.39 (19)C31—C32—H32C109.5
C4—C4A—C8A116.59 (19)H32A—C32—H32C109.5
C5—C4A—C8A120.02 (18)H32B—C32—H32C109.5
C6—C5—C4A121.2 (2)C41—O41—C4120.30 (16)
C6—C5—H5119.4O42—C41—O41122.97 (19)
C4A—C5—H5119.4O42—C41—C42126.9 (2)
C5—C6—C7118.4 (2)O41—C41—C42110.09 (19)
C5—C6—C61120.50 (19)C41—C42—H42A109.5
C7—C6—C61121.08 (19)C41—C42—H42B109.5
C8—C7—C6123.0 (2)H42A—C42—H42B109.5
C8—C7—H7118.5C41—C42—H42C109.5
C6—C7—H7118.5H42A—C42—H42C109.5
C7—C8—C8A118.48 (19)H42B—C42—H42C109.5
C7—C8—C81121.14 (18)C6—C61—H61A109.5
C8A—C8—C81120.37 (18)C6—C61—H61B109.5
N1—C8A—C4A122.58 (18)H61A—C61—H61B109.5
N1—C8A—C8118.57 (18)C6—C61—H61C109.5
C4A—C8A—C8118.85 (19)H61A—C61—H61C109.5
C22—C21—C26118.4 (2)H61B—C61—H61C109.5
C22—C21—C2122.01 (18)C82—C81—C8116.28 (18)
C26—C21—C2119.60 (19)C82—C81—H81A108.2
C23—C22—C21121.0 (2)C8—C81—H81A108.2
C23—C22—H22119.5C82—C81—H81B108.2
C21—C22—H22119.5C8—C81—H81B108.2
C24—C23—C22120.1 (2)H81A—C81—H81B107.4
C24—C23—H23120.0C83—C82—C81126.3 (2)
C22—C23—H23120.0C83—C82—H82116.8
C23—C24—C25120.0 (2)C81—C82—H82116.8
C23—C24—H24120.0C82—C83—H83A120.0
C25—C24—H24120.0C82—C83—H83B120.0
C26—C25—C24120.2 (2)H83A—C83—H83B120.0
C26—C25—H25119.9
C8A—N1—C2—C30.8 (3)C7—C8—C8A—N1179.77 (19)
C8A—N1—C2—C21178.65 (18)C81—C8—C8A—N11.9 (3)
N1—C2—C3—C40.8 (3)C7—C8—C8A—C4A1.0 (3)
C21—C2—C3—C4176.93 (19)C81—C8—C8A—C4A177.41 (19)
N1—C2—C3—C31178.7 (2)N1—C2—C21—C22136.2 (2)
C21—C2—C3—C313.5 (3)C3—C2—C21—C2241.7 (3)
C2—C3—C4—O41173.28 (18)N1—C2—C21—C2641.9 (3)
C31—C3—C4—O417.2 (3)C3—C2—C21—C26140.2 (2)
C2—C3—C4—C4A2.6 (3)C26—C21—C22—C230.2 (3)
C31—C3—C4—C4A176.9 (2)C2—C21—C22—C23178.3 (2)
C3—C4—C4A—C5177.6 (2)C21—C22—C23—C240.7 (3)
O41—C4—C4A—C56.2 (3)C22—C23—C24—C250.9 (4)
C3—C4—C4A—C8A2.7 (3)C23—C24—C25—C260.0 (4)
O41—C4—C4A—C8A173.49 (18)C24—C25—C26—C211.0 (3)
C4—C4A—C5—C6178.9 (2)C22—C21—C26—C251.1 (3)
C8A—C4A—C5—C60.7 (3)C2—C21—C26—C25179.2 (2)
C4A—C5—C6—C70.5 (3)C4—C3—C31—O3158.0 (3)
C4A—C5—C6—C61179.6 (2)C2—C3—C31—O31122.5 (2)
C5—C6—C7—C81.0 (3)C4—C3—C31—C32119.1 (2)
C61—C6—C7—C8179.9 (2)C2—C3—C31—C3260.4 (3)
C6—C7—C8—C8A0.3 (3)C3—C4—O41—C4162.0 (3)
C6—C7—C8—C81178.66 (19)C4A—C4—O41—C41121.8 (2)
C2—N1—C8A—C4A0.7 (3)C4—O41—C41—O421.6 (3)
C2—N1—C8A—C8179.89 (19)C4—O41—C41—C42177.67 (18)
C4—C4A—C8A—N11.0 (3)C7—C8—C81—C82105.9 (2)
C5—C4A—C8A—N1179.28 (19)C8A—C8—C81—C8275.8 (3)
C4—C4A—C8A—C8178.22 (19)C8—C81—C82—C839.1 (3)
C5—C4A—C8A—C81.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O31i0.952.473.366 (3)158
C25—H25···O31ii0.952.603.482 (3)155
C32—H32A···O42i0.982.563.527 (3)170
C61—H61B···O42iii0.982.583.414 (3)143
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y, z; (iii) x, y, z+1.
(VII) (2RS)-2,8-Dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one top
Crystal data top
C19H17NOF(000) = 1168
Mr = 275.33Dx = 1.306 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.756 (5) ÅCell parameters from 3212 reflections
b = 10.364 (3) Åθ = 3.4–27.5°
c = 15.232 (4) ŵ = 0.08 mm1
β = 92.774 (8)°T = 120 K
V = 2799.7 (14) Å3Block, colourless
Z = 80.32 × 0.25 × 0.16 mm
Data collection top
Bruker D8 Venture
diffractometer
3211 independent reflections
Radiation source: high brilliance microfocus sealed tube2042 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.076
φ and ω scansθmax = 27.5°, θmin = 3.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2223
Tmin = 0.912, Tmax = 0.987k = 1313
16087 measured reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0374P)2 + 3.8913P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3211 reflectionsΔρmax = 0.35 e Å3
192 parametersΔρmin = 0.27 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
C10.35524 (12)0.4701 (2)0.09788 (14)0.0234 (5)
H1A0.30960.42070.07890.028*
H1B0.39590.45020.05780.028*
C20.33840 (12)0.6179 (2)0.09894 (13)0.0199 (4)
H20.36310.66220.04960.024*
N30.37332 (9)0.66015 (16)0.18562 (11)0.0182 (4)
C3A0.39097 (10)0.5546 (2)0.23759 (13)0.0171 (4)
C40.37897 (11)0.7807 (2)0.22030 (13)0.0181 (4)
C50.40447 (12)0.7960 (2)0.30645 (13)0.0216 (4)
H50.40730.88110.32960.026*
C60.42726 (11)0.6906 (2)0.36393 (13)0.0200 (4)
O60.45365 (9)0.70669 (15)0.44093 (9)0.0275 (4)
C6A0.41745 (10)0.5624 (2)0.32476 (12)0.0174 (4)
C70.43394 (11)0.4444 (2)0.36742 (13)0.0189 (4)
H70.45280.44520.42690.023*
C80.42334 (11)0.3272 (2)0.32467 (13)0.0194 (4)
C90.39523 (11)0.3250 (2)0.23566 (13)0.0195 (4)
H90.38730.24490.20640.023*
C9A0.37961 (11)0.4384 (2)0.19205 (13)0.0188 (4)
C210.25443 (12)0.6450 (2)0.09482 (15)0.0264 (5)
H21A0.23100.60030.14320.040*
H21B0.23200.61410.03860.040*
H21C0.24600.73810.09990.040*
C410.36044 (11)0.8936 (2)0.16205 (13)0.0186 (4)
C420.29734 (12)0.9699 (2)0.17538 (15)0.0237 (5)
H420.26480.94900.22090.028*
C430.28190 (12)1.0771 (2)0.12198 (15)0.0266 (5)
H430.23841.12810.13060.032*
C440.33008 (12)1.1088 (2)0.05644 (14)0.0234 (5)
H440.32011.18250.02060.028*
C450.39300 (11)1.0327 (2)0.04308 (13)0.0209 (4)
H450.42601.05470.00190.025*
C460.40787 (11)0.9251 (2)0.09485 (13)0.0195 (4)
H460.45040.87260.08460.023*
C810.44411 (12)0.2013 (2)0.36924 (14)0.0242 (5)
H81A0.47480.21860.42310.036*
H81B0.47290.14810.32960.036*
H81C0.39810.15560.38400.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0271 (11)0.0223 (11)0.0204 (10)0.0002 (9)0.0027 (8)0.0046 (9)
C20.0253 (10)0.0210 (10)0.0132 (9)0.0037 (8)0.0026 (8)0.0016 (8)
N30.0189 (8)0.0207 (9)0.0150 (8)0.0020 (7)0.0002 (6)0.0025 (7)
C3A0.0135 (9)0.0210 (10)0.0170 (9)0.0005 (8)0.0020 (7)0.0004 (8)
C40.0162 (9)0.0192 (10)0.0191 (10)0.0041 (8)0.0034 (7)0.0013 (8)
C50.0250 (11)0.0193 (10)0.0207 (10)0.0057 (8)0.0038 (8)0.0048 (8)
C60.0204 (10)0.0231 (11)0.0167 (10)0.0064 (8)0.0028 (8)0.0023 (8)
O60.0385 (9)0.0271 (8)0.0164 (7)0.0073 (7)0.0036 (6)0.0038 (6)
C6A0.0143 (9)0.0218 (10)0.0162 (9)0.0025 (8)0.0022 (7)0.0023 (8)
C70.0143 (9)0.0273 (11)0.0153 (9)0.0018 (8)0.0007 (7)0.0016 (9)
C80.0150 (9)0.0220 (11)0.0213 (10)0.0009 (8)0.0022 (8)0.0022 (8)
C90.0179 (10)0.0199 (10)0.0207 (10)0.0000 (8)0.0001 (8)0.0059 (8)
C9A0.0163 (9)0.0234 (10)0.0167 (9)0.0004 (8)0.0002 (7)0.0037 (8)
C210.0256 (11)0.0232 (11)0.0295 (12)0.0013 (9)0.0081 (9)0.0009 (9)
C410.0188 (10)0.0185 (10)0.0184 (10)0.0042 (8)0.0009 (8)0.0025 (8)
C420.0224 (11)0.0229 (11)0.0263 (11)0.0032 (8)0.0066 (8)0.0040 (9)
C430.0210 (10)0.0229 (12)0.0357 (12)0.0026 (8)0.0004 (9)0.0071 (10)
C440.0247 (10)0.0169 (10)0.0280 (11)0.0024 (8)0.0061 (8)0.0023 (9)
C450.0209 (10)0.0223 (11)0.0195 (10)0.0060 (8)0.0001 (8)0.0019 (8)
C460.0170 (9)0.0215 (11)0.0199 (10)0.0024 (8)0.0013 (8)0.0026 (8)
C810.0245 (11)0.0239 (11)0.0240 (11)0.0004 (9)0.0018 (9)0.0013 (9)
Geometric parameters (Å, º) top
C1—C9A1.514 (3)C8—C811.508 (3)
C1—C21.561 (3)C9—C9A1.372 (3)
C1—H1A0.9900C9—H90.9500
C1—H1B0.9900C21—H21A0.9800
C2—N31.497 (2)C21—H21B0.9800
C2—C211.515 (3)C21—H21C0.9800
C2—H21.0000C41—C421.394 (3)
N3—C41.358 (3)C41—C461.395 (3)
N3—C3A1.377 (3)C42—C431.396 (3)
C3A—C6A1.389 (3)C42—H420.9500
C3A—C9A1.399 (3)C43—C441.385 (3)
C4—C51.376 (3)C43—H430.9500
C4—C411.496 (3)C44—C451.391 (3)
C5—C61.446 (3)C44—H440.9500
C5—H50.9500C45—C461.384 (3)
C6—O61.253 (2)C45—H450.9500
C6—C6A1.463 (3)C46—H460.9500
C6A—C71.409 (3)C81—H81A0.9800
C7—C81.387 (3)C81—H81B0.9800
C7—H70.9500C81—H81C0.9800
C8—C91.422 (3)
C9A—C1—C2104.42 (16)C9A—C9—C8120.09 (19)
C9A—C1—H1A110.9C9A—C9—H9120.0
C2—C1—H1A110.9C8—C9—H9120.0
C9A—C1—H1B110.9C9—C9A—C3A118.44 (18)
C2—C1—H1B110.9C9—C9A—C1133.33 (19)
H1A—C1—H1B108.9C3A—C9A—C1108.12 (18)
N3—C2—C21110.32 (17)C2—C21—H21A109.5
N3—C2—C1102.98 (16)C2—C21—H21B109.5
C21—C2—C1111.70 (17)H21A—C21—H21B109.5
N3—C2—H2110.5C2—C21—H21C109.5
C21—C2—H2110.5H21A—C21—H21C109.5
C1—C2—H2110.5H21B—C21—H21C109.5
C4—N3—C3A119.76 (17)C42—C41—C46119.5 (2)
C4—N3—C2129.18 (17)C42—C41—C4120.85 (18)
C3A—N3—C2110.36 (16)C46—C41—C4119.65 (18)
N3—C3A—C6A124.07 (19)C41—C42—C43120.2 (2)
N3—C3A—C9A112.03 (17)C41—C42—H42119.9
C6A—C3A—C9A123.9 (2)C43—C42—H42119.9
N3—C4—C5119.45 (19)C44—C43—C42119.9 (2)
N3—C4—C41118.63 (18)C44—C43—H43120.1
C5—C4—C41121.86 (19)C42—C43—H43120.1
C4—C5—C6124.03 (19)C43—C44—C45120.0 (2)
C4—C5—H5118.0C43—C44—H44120.0
C6—C5—H5118.0C45—C44—H44120.0
O6—C6—C5123.16 (19)C46—C45—C44120.40 (19)
O6—C6—C6A122.3 (2)C46—C45—H45119.8
C5—C6—C6A114.52 (18)C44—C45—H45119.8
C3A—C6A—C7116.33 (19)C45—C46—C41120.08 (19)
C3A—C6A—C6118.07 (19)C45—C46—H46120.0
C7—C6A—C6125.58 (18)C41—C46—H46120.0
C8—C7—C6A121.55 (18)C8—C81—H81A109.5
C8—C7—H7119.2C8—C81—H81B109.5
C6A—C7—H7119.2H81A—C81—H81B109.5
C7—C8—C9119.67 (19)C8—C81—H81C109.5
C7—C8—C81121.44 (19)H81A—C81—H81C109.5
C9—C8—C81118.83 (19)H81B—C81—H81C109.5
C9A—C1—C2—N314.0 (2)C3A—C6A—C7—C80.7 (3)
C9A—C1—C2—C21104.33 (19)C6—C6A—C7—C8179.5 (2)
C21—C2—N3—C463.9 (3)C6A—C7—C8—C90.0 (3)
C1—C2—N3—C4176.72 (19)C6A—C7—C8—C81177.38 (19)
C21—C2—N3—C3A106.25 (19)C7—C8—C9—C9A0.8 (3)
C1—C2—N3—C3A13.1 (2)C81—C8—C9—C9A176.60 (19)
C4—N3—C3A—C6A2.4 (3)C8—C9—C9A—C3A0.9 (3)
C2—N3—C3A—C6A173.63 (18)C8—C9—C9A—C1174.8 (2)
C4—N3—C3A—C9A178.04 (18)N3—C3A—C9A—C9179.74 (18)
C2—N3—C3A—C9A6.8 (2)C6A—C3A—C9A—C90.2 (3)
C3A—N3—C4—C51.9 (3)N3—C3A—C9A—C13.0 (2)
C2—N3—C4—C5171.31 (19)C6A—C3A—C9A—C1176.54 (18)
C3A—N3—C4—C41179.19 (17)C2—C1—C9A—C9173.1 (2)
C2—N3—C4—C4111.4 (3)C2—C1—C9A—C3A10.9 (2)
N3—C4—C5—C60.9 (3)N3—C4—C41—C42112.5 (2)
C41—C4—C5—C6176.29 (19)C5—C4—C41—C4270.3 (3)
C4—C5—C6—O6176.6 (2)N3—C4—C41—C4669.1 (2)
C4—C5—C6—C6A3.1 (3)C5—C4—C41—C46108.1 (2)
N3—C3A—C6A—C7178.87 (18)C46—C41—C42—C430.1 (3)
C9A—C3A—C6A—C70.6 (3)C4—C41—C42—C43178.28 (19)
N3—C3A—C6A—C60.0 (3)C41—C42—C43—C441.0 (3)
C9A—C3A—C6A—C6179.51 (18)C42—C43—C44—C451.0 (3)
O6—C6—C6A—C3A177.11 (19)C43—C44—C45—C460.1 (3)
C5—C6—C6A—C3A2.6 (3)C44—C45—C46—C411.2 (3)
O6—C6—C6A—C71.6 (3)C42—C41—C46—C451.2 (3)
C5—C6—C6A—C7178.69 (19)C4—C41—C46—C45177.19 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C46—H46···O6i0.952.463.405 (3)171
Symmetry code: (i) x+1, y, z+1/2.
 

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