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Two spiro­[indoline-3,3′-pyrrolizine] derivatives have been synthesized in good yield with high regio- and stereospecificity using one-pot reactions between readily available starting materials, namely L-proline, substituted 1H-indole-2,3-diones and electron-deficient alkenes. The products have been fully characterized by elemental analysis, IR and NMR spectroscopy, mass spectrometry and crystal structure analysis. In (1′RS,2′RS,3SR,7a′SR)-2′-benzoyl-1-hexyl-2-oxo-1′,2′,5′,6′,7′,7a′-hexa­hydro­spiro­[indoline-3,3′-pyrrolizine]-1′-carb­oxy­lic acid, C28H32N2O4, (I), the unsubstituted pyrrole ring and the reduced spiro-fused pyrrole ring adopt half-chair and envelope conformations, respectively, while in (1′RS,2′RS,3SR,7a′SR)-1′,2′-bis­(4-chloro­benzo­yl)-5,7-di­chloro-2-oxo-1′,2′,5′,6′,7′,7a′-hexa­hydro­spiro­[indoline-3,3′-pyrrolizine], which crystallizes as a partial di­chloro­methane solvate, C28H20Cl4N2O3·0.981CH2Cl2, (II), where the solvent component is disordered over three sets of atomic sites, these two rings adopt envelope and half-chair conformations, respectively. Mol­ecules of (I) are linked by an O—H...·O hydrogen bond to form cyclic R66(48) hexa­mers of \overline{3} (S6) symmetry, which are further linked by two C—H...O hydrogen bonds to form a three-dimensional framework structure. In compound (II), inversion-related pairs of N—H...O hydrogen bonds link the spiro­[indoline-3,3′-pyrrolizine] mol­ecules into simple R22(8) dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617016072/sk3676sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676IIsup3.hkl
Contains datablock II

CCDC references: 1584355; 1584354

Computing details top

Data collection: APEX3 Bruker, 2016) for (I); APEX3 (Bruker, 2016) for (II). For both structures, cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS86 (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).

(1'RS,2'RS,3SR,7a'SR)-2'-Benzoyl-1-hexyl-2-oxo-\ 1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-1'-carboxylic acid (I) top
Crystal data top
C28H32N2O4Dx = 1.312 Mg m3
Mr = 460.56Mo Kα radiation, λ = 0.71073 Å
Rhombohedral, R3:RCell parameters from 5197 reflections
a = 19.9182 (9) Åθ = 2.4–27.2°
α = 116.980 (2)°µ = 0.09 mm1
V = 3496.4 (11) Å3T = 100 K
Z = 6Plate, colourless
F(000) = 14760.27 × 0.21 × 0.13 mm
Data collection top
Bruker D8 Venture
diffractometer
5194 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3672 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.067
φ and ω scansθmax = 27.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2524
Tmin = 0.959, Tmax = 0.989k = 2125
35458 measured reflectionsl = 2525
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.046P)2 + 2.8884P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5194 reflectionsΔρmax = 0.59 e Å3
311 parametersΔρmin = 0.35 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
N110.28565 (15)0.30066 (15)0.64134 (15)0.0136 (3)
C120.18369 (18)0.17781 (18)0.50967 (18)0.0127 (4)
O120.06331 (12)0.08598 (13)0.42607 (12)0.0160 (3)
C130.24343 (18)0.17338 (18)0.48159 (18)0.0123 (4)
C13A0.39408 (18)0.30705 (18)0.62340 (18)0.0128 (4)
C140.50565 (19)0.36345 (19)0.67287 (19)0.0161 (4)
H140.49480.31440.61440.019*
C150.63468 (19)0.49387 (19)0.81038 (19)0.0188 (4)
H150.71210.53290.84620.023*
C160.65064 (19)0.56663 (19)0.89490 (19)0.0177 (4)
H160.73920.65640.98740.021*
C170.53910 (19)0.51055 (19)0.84676 (19)0.0164 (4)
H170.54970.56010.90450.020*
C17A0.41287 (18)0.38007 (18)0.71179 (18)0.0126 (4)
C210.17448 (18)0.00668 (18)0.31007 (18)0.0133 (4)
H210.26520.06470.36160.016*
C220.18358 (18)0.04304 (18)0.40260 (18)0.0124 (4)
H220.08980.03050.34510.015*
N240.19334 (16)0.15696 (16)0.38496 (15)0.0150 (3)
C250.2857 (2)0.2729 (2)0.4332 (2)0.0210 (5)
H25A0.36930.35790.53330.025*
H25B0.24180.28180.39830.025*
C260.3174 (2)0.2422 (2)0.3787 (2)0.0235 (5)
H26A0.38970.26700.43670.028*
H26B0.34450.29000.37040.028*
C270.1820 (2)0.0895 (2)0.2404 (2)0.0225 (5)
H27B0.19410.04890.20740.027*
H27C0.11910.06680.17320.027*
C27A0.1301 (2)0.04066 (19)0.26696 (19)0.0160 (4)
H27A0.02940.03820.18640.019*
C1110.26698 (19)0.3384 (2)0.70535 (19)0.0174 (4)
H11A0.16910.26680.63450.021*
H11B0.31080.42310.75190.021*
C1120.3266 (2)0.3588 (2)0.8082 (2)0.0227 (5)
H11C0.34840.32280.79660.027*
H11D0.41240.45700.90050.027*
C1130.2346 (2)0.2917 (2)0.7967 (2)0.0296 (5)
H11E0.15360.19260.70800.035*
H11F0.28270.31170.86740.035*
C1140.1875 (2)0.3315 (2)0.8094 (2)0.0308 (5)
H11G0.12780.29960.73120.037*
H11H0.13290.28470.80510.037*
C1150.2999 (2)0.4808 (2)0.9372 (2)0.0336 (6)
H11I0.34430.52680.93450.040*
H11J0.36830.51651.01560.040*
C1160.2467 (3)0.5124 (3)0.9559 (3)0.0396 (6)
H11K0.17560.47300.87630.059*
H11L0.32110.61051.03660.059*
H11M0.20970.47350.96650.059*
C2110.07168 (19)0.14083 (19)0.18908 (18)0.0151 (4)
O2110.03088 (14)0.22926 (13)0.13510 (14)0.0254 (4)
O2120.10475 (14)0.16276 (14)0.14691 (14)0.0220 (3)
H2120.041 (2)0.249 (2)0.076 (2)0.026*
C2270.26501 (18)0.06015 (17)0.49367 (18)0.0131 (4)
O2270.33092 (13)0.06284 (13)0.50208 (13)0.0186 (3)
C2210.26486 (19)0.07644 (18)0.57438 (19)0.0153 (4)
C2220.1553 (2)0.01930 (19)0.5305 (2)0.0187 (4)
H2220.07910.02850.44860.022*
C2230.1567 (2)0.0318 (2)0.6057 (2)0.0240 (5)
H2230.08070.00930.57430.029*
C2240.2691 (2)0.1044 (2)0.7267 (2)0.0279 (5)
H2240.27080.11430.77900.033*
C2250.3787 (2)0.1625 (2)0.7715 (2)0.0279 (5)
H2250.45600.21320.85520.033*
C2260.3765 (2)0.1474 (2)0.6954 (2)0.0217 (5)
H2260.45120.18550.72550.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0124 (8)0.0151 (8)0.0121 (8)0.0113 (7)0.0104 (7)0.0109 (7)
C120.0154 (9)0.0153 (9)0.0126 (9)0.0132 (9)0.0116 (9)0.0127 (9)
O120.0112 (6)0.0163 (7)0.0120 (6)0.0107 (6)0.0090 (6)0.0108 (6)
C130.0136 (9)0.0141 (9)0.0126 (9)0.0118 (8)0.0111 (8)0.0115 (8)
C13A0.0153 (9)0.0123 (9)0.0138 (9)0.0115 (8)0.0122 (8)0.0114 (8)
C140.0174 (10)0.0150 (9)0.0184 (10)0.0138 (9)0.0155 (9)0.0136 (9)
C150.0143 (9)0.0167 (10)0.0200 (10)0.0123 (9)0.0140 (9)0.0147 (9)
C160.0127 (9)0.0116 (9)0.0144 (9)0.0087 (9)0.0098 (9)0.0097 (9)
C170.0177 (10)0.0143 (9)0.0149 (9)0.0132 (9)0.0134 (9)0.0117 (9)
C17A0.0128 (9)0.0144 (9)0.0148 (9)0.0116 (8)0.0114 (8)0.0129 (8)
C210.0120 (9)0.0124 (9)0.0110 (9)0.0096 (8)0.0096 (8)0.0090 (8)
C220.0102 (9)0.0090 (8)0.0099 (9)0.0071 (8)0.0078 (8)0.0070 (8)
N240.0203 (8)0.0173 (8)0.0146 (8)0.0162 (8)0.0151 (8)0.0141 (7)
C250.0319 (11)0.0234 (10)0.0246 (11)0.0244 (10)0.0248 (10)0.0217 (10)
C260.0353 (12)0.0276 (11)0.0328 (12)0.0276 (11)0.0309 (11)0.0278 (11)
C270.0357 (12)0.0288 (11)0.0243 (11)0.0286 (11)0.0271 (11)0.0239 (10)
C27A0.0178 (9)0.0170 (9)0.0130 (9)0.0146 (9)0.0126 (9)0.0125 (9)
C1110.0164 (9)0.0185 (10)0.0152 (9)0.0149 (9)0.0134 (9)0.0128 (9)
C1120.0263 (11)0.0272 (11)0.0237 (11)0.0228 (10)0.0221 (10)0.0217 (10)
C1130.0258 (12)0.0280 (12)0.0225 (11)0.0203 (11)0.0202 (11)0.0197 (11)
C1140.0310 (12)0.0347 (13)0.0313 (12)0.0267 (12)0.0272 (11)0.0279 (12)
C1150.0288 (12)0.0330 (13)0.0324 (13)0.0243 (12)0.0244 (12)0.0278 (12)
C1160.0353 (14)0.0413 (14)0.0438 (15)0.0325 (13)0.0336 (13)0.0343 (14)
C2110.0154 (9)0.0147 (9)0.0125 (9)0.0122 (9)0.0113 (8)0.0110 (8)
O2110.0171 (7)0.0137 (7)0.0214 (7)0.0102 (7)0.0157 (7)0.0109 (7)
O2120.0192 (7)0.0111 (7)0.0173 (7)0.0104 (6)0.0156 (7)0.0086 (6)
C2270.0108 (9)0.0073 (8)0.0100 (9)0.0064 (8)0.0075 (8)0.0063 (8)
O2270.0200 (7)0.0210 (7)0.0205 (7)0.0178 (7)0.0173 (7)0.0174 (7)
C2210.0171 (9)0.0124 (9)0.0155 (9)0.0119 (9)0.0133 (9)0.0119 (9)
C2220.0181 (10)0.0168 (10)0.0191 (10)0.0138 (9)0.0153 (9)0.0151 (9)
C2230.0269 (11)0.0244 (11)0.0303 (11)0.0211 (10)0.0256 (11)0.0236 (10)
C2240.0358 (12)0.0290 (12)0.0269 (11)0.0257 (11)0.0278 (11)0.0247 (11)
C2250.0272 (12)0.0308 (12)0.0203 (11)0.0228 (11)0.0190 (10)0.0217 (11)
C2260.0208 (10)0.0241 (11)0.0190 (10)0.0185 (10)0.0164 (10)0.0179 (10)
Geometric parameters (Å, º) top
N11—C121.351 (2)C27A—H27A1.0000
N11—C17A1.419 (2)C111—C1121.540 (3)
N11—C1111.464 (2)C111—H11A0.9900
C12—O121.225 (2)C111—H11B0.9900
C12—C131.546 (3)C112—C1131.521 (3)
C13—N241.482 (2)C112—H11C0.9900
C13—C13A1.519 (3)C112—H11D0.9900
C13—C221.556 (3)C113—C1141.511 (3)
C13A—C141.384 (3)C113—H11E0.9900
C13A—C17A1.393 (3)C113—H11F0.9900
C14—C151.398 (3)C114—C1151.502 (3)
C14—H140.9500C114—H11G0.9900
C15—C161.385 (3)C114—H11H0.9900
C15—H150.9500C115—C1161.551 (3)
C16—C171.395 (3)C115—H11I0.9900
C16—H160.9500C115—H11J0.9900
C17—C17A1.379 (3)C116—H11K0.9800
C17—H170.9500C116—H11L0.9800
C21—C2111.507 (3)C116—H11M0.9800
C21—C221.524 (3)C211—O2111.206 (2)
C21—C27A1.536 (3)C211—O2121.327 (2)
C21—H211.0000O212—H2120.87 (2)
C22—C2271.518 (3)C227—O2271.218 (2)
C22—H221.0000C227—C2211.490 (3)
N24—C251.472 (3)C221—C2221.392 (3)
N24—C27A1.484 (2)C221—C2261.395 (3)
C25—C261.525 (3)C222—C2231.387 (3)
C25—H25A0.9900C222—H2220.9500
C25—H25B0.9900C223—C2241.385 (3)
C26—C271.526 (3)C223—H2230.9500
C26—H26A0.9900C224—C2251.378 (3)
C26—H26B0.9900C224—H2240.9500
C27—C27A1.532 (3)C225—C2261.382 (3)
C27—H27B0.9900C225—H2250.9500
C27—H27C0.9900C226—H2260.9500
C12—N11—C17A110.72 (15)C27—C27A—C21115.22 (16)
C12—N11—C111124.01 (16)N24—C27A—H27A110.2
C17A—N11—C111124.73 (15)C27—C27A—H27A110.2
O12—C12—N11125.14 (18)C21—C27A—H27A110.2
O12—C12—C13125.83 (17)N11—C111—C112112.56 (16)
N11—C12—C13109.01 (15)N11—C111—H11A109.1
N24—C13—C13A116.59 (15)C112—C111—H11A109.1
N24—C13—C12107.28 (14)N11—C111—H11B109.1
C13A—C13—C12101.39 (14)C112—C111—H11B109.1
N24—C13—C22103.51 (14)H11A—C111—H11B107.8
C13A—C13—C22116.71 (15)C113—C112—C111114.72 (18)
C12—C13—C22111.19 (15)C113—C112—H11C108.6
C14—C13A—C17A119.41 (17)C111—C112—H11C108.6
C14—C13A—C13132.13 (17)C113—C112—H11D108.6
C17A—C13A—C13108.44 (16)C111—C112—H11D108.6
C13A—C14—C15118.81 (18)H11C—C112—H11D107.6
C13A—C14—H14120.6C114—C113—C112117.0 (2)
C15—C14—H14120.6C114—C113—H11E108.1
C16—C15—C14120.59 (18)C112—C113—H11E108.1
C16—C15—H15119.7C114—C113—H11F108.1
C14—C15—H15119.7C112—C113—H11F108.1
C15—C16—C17121.21 (18)H11E—C113—H11F107.3
C15—C16—H16119.4C115—C114—C113114.2 (2)
C17—C16—H16119.4C115—C114—H11G108.7
C17A—C17—C16117.12 (18)C113—C114—H11G108.7
C17A—C17—H17121.4C115—C114—H11H108.7
C16—C17—H17121.4C113—C114—H11H108.7
C17—C17A—C13A122.75 (17)H11G—C114—H11H107.6
C17—C17A—N11127.36 (17)C114—C115—C116111.5 (2)
C13A—C17A—N11109.89 (16)C114—C115—H11I109.3
C211—C21—C22112.18 (15)C116—C115—H11I109.3
C211—C21—C27A110.95 (15)C114—C115—H11J109.3
C22—C21—C27A102.12 (15)C116—C115—H11J109.3
C211—C21—H21110.4H11I—C115—H11J108.0
C22—C21—H21110.4C115—C116—H11K109.5
C27A—C21—H21110.4C115—C116—H11L109.5
C227—C22—C21113.89 (15)H11K—C116—H11L109.5
C227—C22—C13113.48 (15)C115—C116—H11M109.5
C21—C22—C13104.09 (14)H11K—C116—H11M109.5
C227—C22—H22108.4H11L—C116—H11M109.5
C21—C22—H22108.4O211—C211—O212123.90 (18)
C13—C22—H22108.4O211—C211—C21123.33 (17)
C25—N24—C13119.60 (15)O212—C211—C21112.75 (16)
C25—N24—C27A108.43 (15)C211—O212—H212109.3 (15)
C13—N24—C27A110.41 (14)O227—C227—C221120.88 (17)
N24—C25—C26105.22 (15)O227—C227—C22120.39 (17)
N24—C25—H25A110.7C221—C227—C22118.72 (16)
C26—C25—H25A110.7C222—C221—C226119.25 (18)
N24—C25—H25B110.7C222—C221—C227122.06 (17)
C26—C25—H25B110.7C226—C221—C227118.65 (18)
H25A—C25—H25B108.8C223—C222—C221120.28 (19)
C25—C26—C27101.68 (17)C223—C222—H222119.9
C25—C26—H26A111.4C221—C222—H222119.9
C27—C26—H26A111.4C224—C223—C222119.8 (2)
C25—C26—H26B111.4C224—C223—H223120.1
C27—C26—H26B111.4C222—C223—H223120.1
H26A—C26—H26B109.3C225—C224—C223120.2 (2)
C26—C27—C27A103.40 (16)C225—C224—H224119.9
C26—C27—H27B111.1C223—C224—H224119.9
C27A—C27—H27B111.1C224—C225—C226120.3 (2)
C26—C27—H27C111.1C224—C225—H225119.8
C27A—C27—H27C111.1C226—C225—H225119.8
H27B—C27—H27C109.0C225—C226—C221120.1 (2)
N24—C27A—C27105.61 (15)C225—C226—H226120.0
N24—C27A—C21105.07 (14)C221—C226—H226120.0
C17A—N11—C12—O12176.43 (17)C13A—C13—N24—C27A119.76 (17)
C111—N11—C12—O124.5 (3)C12—C13—N24—C27A127.47 (16)
C17A—N11—C12—C134.7 (2)C22—C13—N24—C27A9.83 (18)
C111—N11—C12—C13176.63 (16)C13—N24—C25—C26106.85 (19)
O12—C12—C13—N2463.1 (2)C27A—N24—C25—C2620.9 (2)
N11—C12—C13—N24115.74 (16)N24—C25—C26—C2736.7 (2)
O12—C12—C13—C13A174.14 (18)C25—C26—C27—C27A38.3 (2)
N11—C12—C13—C13A7.00 (19)C25—N24—C27A—C273.6 (2)
O12—C12—C13—C2249.4 (2)C13—N24—C27A—C27136.37 (16)
N11—C12—C13—C22131.74 (16)C25—N24—C27A—C21118.67 (16)
N24—C13—C13A—C1469.0 (3)C13—N24—C27A—C2114.13 (19)
C12—C13—C13A—C14174.9 (2)C26—C27—C27A—N2426.4 (2)
C22—C13—C13A—C1453.9 (3)C26—C27—C27A—C2189.02 (19)
N24—C13—C13A—C17A109.22 (18)C211—C21—C27A—N24152.19 (15)
C12—C13—C13A—C17A6.86 (19)C22—C21—C27A—N2432.47 (18)
C22—C13—C13A—C17A127.80 (17)C211—C21—C27A—C2792.03 (19)
C17A—C13A—C14—C151.3 (3)C22—C21—C27A—C27148.25 (16)
C13—C13A—C14—C15176.82 (19)C12—N11—C111—C112111.4 (2)
C13A—C14—C15—C161.6 (3)C17A—N11—C111—C11259.4 (2)
C14—C15—C16—C172.3 (3)N11—C111—C112—C113134.04 (19)
C15—C16—C17—C17A0.1 (3)C111—C112—C113—C11457.4 (3)
C16—C17—C17A—C13A2.9 (3)C112—C113—C114—C11555.4 (3)
C16—C17—C17A—N11177.67 (18)C113—C114—C115—C116170.0 (2)
C14—C13A—C17A—C173.7 (3)C22—C21—C211—O21133.0 (3)
C13—C13A—C17A—C17174.86 (17)C27A—C21—C211—O21180.5 (2)
C14—C13A—C17A—N11176.84 (16)C22—C21—C211—O212148.45 (16)
C13—C13A—C17A—N114.6 (2)C27A—C21—C211—O21298.03 (19)
C12—N11—C17A—C17179.56 (18)C21—C22—C227—O2279.8 (2)
C111—N11—C17A—C178.6 (3)C13—C22—C227—O227109.04 (19)
C12—N11—C17A—C13A0.1 (2)C21—C22—C227—C221171.46 (15)
C111—N11—C17A—C13A171.94 (17)C13—C22—C227—C22169.7 (2)
C211—C21—C22—C22778.58 (19)O227—C227—C221—C222151.83 (18)
C27A—C21—C22—C227162.57 (15)C22—C227—C221—C22229.5 (3)
C211—C21—C22—C13157.34 (15)O227—C227—C221—C22626.0 (3)
C27A—C21—C22—C1338.49 (17)C22—C227—C221—C226152.74 (17)
N24—C13—C22—C227154.56 (15)C226—C221—C222—C2230.6 (3)
C13A—C13—C22—C22725.0 (2)C227—C221—C222—C223177.16 (18)
C12—C13—C22—C22790.56 (18)C221—C222—C223—C2241.7 (3)
N24—C13—C22—C2130.21 (17)C222—C223—C224—C2251.0 (3)
C13A—C13—C22—C2199.30 (17)C223—C224—C225—C2260.8 (3)
C12—C13—C22—C21145.09 (15)C224—C225—C226—C2211.8 (3)
C13A—C13—N24—C257.1 (2)C222—C221—C226—C2251.1 (3)
C12—C13—N24—C25105.71 (18)C227—C221—C226—C225178.98 (19)
C22—C13—N24—C25136.64 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O212—H212···O12i0.87 (3)1.79 (3)2.652 (3)176 (4)
C111—H11B···O227ii0.992.463.392 (4)157
C223—H223···O12iii0.952.563.452 (6)156
Symmetry codes: (i) y, z, x; (ii) z+1, x+1, y+1; (iii) x, y, z+1.
(1'RS,2'RS,3SR,7a'SR)-1',2'-Bis(4-chlorobenzoyl)-5,7-dichloro-2-oxo-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine] dichloromethane 0.981-solvate (II) top
Crystal data top
C28H20Cl4N2O3·0.981CH2Cl2F(000) = 1340.8
Mr = 657.57Dx = 1.483 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.800 (4) ÅCell parameters from 6780 reflections
b = 12.511 (5) Åθ = 2.2–27.5°
c = 18.638 (5) ŵ = 0.62 mm1
β = 99.325 (12)°T = 100 K
V = 2945.3 (17) Å3Plate, colourless
Z = 40.38 × 0.35 × 0.16 mm
Data collection top
Bruker D8 Venture
diffractometer
6778 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube6162 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.031
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1616
Tmin = 0.889, Tmax = 0.910k = 1616
92566 measured reflectionsl = 2424
Refinement top
Refinement on F29 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0299P)2 + 2.0129P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6778 reflectionsΔρmax = 0.48 e Å3
397 parametersΔρmin = 0.55 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*/UeqOcc. (<1)
N110.43284 (8)0.61892 (8)0.46172 (5)0.0123 (2)
H110.4751 (12)0.6057 (13)0.5009 (9)0.015*
C120.39675 (9)0.54291 (9)0.41183 (6)0.0114 (2)
O120.41299 (7)0.44655 (7)0.41841 (5)0.01519 (18)
C130.33169 (9)0.59797 (9)0.34400 (6)0.0107 (2)
C13A0.34080 (9)0.71562 (9)0.36652 (6)0.0113 (2)
C140.30039 (10)0.80815 (10)0.33166 (6)0.0136 (2)
H140.25930.80560.28440.016*
C150.32191 (10)0.90520 (10)0.36805 (7)0.0144 (2)
Cl150.27105 (3)1.02188 (2)0.32509 (2)0.02081 (8)
C160.38010 (10)0.91148 (10)0.43773 (7)0.0150 (2)
H160.39280.97860.46140.018*
C170.41944 (10)0.81773 (10)0.47228 (6)0.0139 (2)
Cl170.48725 (3)0.81961 (3)0.56084 (2)0.02249 (8)
C17A0.40057 (9)0.72119 (9)0.43617 (6)0.0114 (2)
C210.28396 (9)0.59190 (9)0.21334 (6)0.0118 (2)
H210.27720.67020.20300.014*
C220.37775 (9)0.57028 (9)0.27360 (6)0.0113 (2)
H220.39440.49220.27400.014*
N240.22596 (8)0.55076 (8)0.32714 (5)0.0118 (2)
C250.14005 (10)0.59019 (11)0.36463 (7)0.0164 (2)
H25A0.15390.66450.38190.020*
H25B0.13210.54410.40660.020*
C260.04113 (10)0.58455 (11)0.30572 (7)0.0180 (3)
H26A0.01370.63580.31570.022*
H26B0.01070.51160.30180.022*
C270.08530 (10)0.61535 (11)0.23659 (7)0.0166 (2)
H27B0.03710.59310.19210.020*
H27C0.09860.69320.23450.020*
C27A0.18843 (9)0.55161 (10)0.24688 (6)0.0123 (2)
H27A0.17220.47650.23030.015*
C2170.29062 (10)0.53006 (10)0.14365 (6)0.0136 (2)
O2170.35076 (8)0.45461 (8)0.14349 (5)0.0233 (2)
C2110.21473 (9)0.55919 (10)0.07655 (6)0.0125 (2)
C2120.17137 (10)0.66137 (10)0.06474 (7)0.0162 (2)
H2120.18740.71460.10120.019*
C2130.10482 (11)0.68601 (10)0.00000 (7)0.0179 (3)
H2130.07700.75610.00850.021*
C2140.08003 (10)0.60648 (11)0.05172 (7)0.0158 (2)
Cl140.00203 (3)0.63716 (3)0.13326 (2)0.02432 (8)
C2150.11886 (10)0.50323 (11)0.04051 (7)0.0167 (2)
H2150.09890.44910.07590.020*
C2160.18744 (10)0.48039 (10)0.02338 (7)0.0154 (2)
H2160.21620.41050.03110.018*
C2270.47804 (10)0.63247 (10)0.26712 (6)0.0132 (2)
O2270.47487 (7)0.71308 (7)0.23002 (5)0.01870 (19)
C2210.57943 (10)0.59336 (10)0.31058 (7)0.0149 (2)
C2220.59639 (11)0.48510 (11)0.32730 (8)0.0197 (3)
H2220.54190.43460.31210.024*
C2230.69288 (11)0.45120 (12)0.36608 (8)0.0240 (3)
H2230.70480.37770.37730.029*
C2240.77115 (11)0.52611 (13)0.38809 (7)0.0237 (3)
Cl240.89258 (3)0.48244 (4)0.43545 (2)0.03470 (10)
C2250.75602 (11)0.63409 (13)0.37267 (8)0.0243 (3)
H2250.81060.68430.38860.029*
C2260.65967 (10)0.66774 (11)0.33350 (7)0.0196 (3)
H2260.64830.74130.32230.023*
C310.2138 (3)0.2919 (10)0.37798 (18)0.0210 (5)0.615 (7)
H31A0.24490.36460.38160.025*0.615 (7)
H31B0.27000.24060.39770.025*0.615 (7)
Cl310.1104 (2)0.28576 (13)0.42976 (12)0.0433 (5)0.615 (7)
Cl320.1673 (2)0.2616 (2)0.28628 (10)0.0365 (5)0.615 (7)
C410.2280 (10)0.293 (3)0.3719 (6)0.0210 (5)0.187 (5)
H41A0.26520.36170.36870.025*0.187 (5)
H41B0.28220.23600.38180.025*0.187 (5)
Cl410.1552 (11)0.2985 (3)0.4443 (2)0.0498 (9)0.187 (5)
Cl420.1467 (14)0.2669 (17)0.2883 (4)0.042 (2)0.187 (5)
C510.2471 (8)0.2952 (10)0.3618 (3)0.0210 (5)0.179 (2)
H51A0.26760.36870.35010.025*0.179 (2)
H51B0.30610.24690.35530.025*0.179 (2)
Cl510.2272 (4)0.2903 (2)0.45308 (15)0.0498 (9)0.179 (2)
Cl520.1333 (12)0.2577 (16)0.3010 (4)0.042 (2)0.179 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0166 (5)0.0099 (5)0.0081 (4)0.0017 (4)0.0045 (4)0.0000 (4)
C120.0133 (5)0.0118 (5)0.0083 (5)0.0001 (4)0.0011 (4)0.0004 (4)
O120.0208 (4)0.0095 (4)0.0128 (4)0.0015 (3)0.0048 (3)0.0008 (3)
C130.0136 (5)0.0090 (5)0.0082 (5)0.0010 (4)0.0021 (4)0.0008 (4)
C13A0.0143 (5)0.0101 (5)0.0092 (5)0.0007 (4)0.0014 (4)0.0007 (4)
C140.0185 (6)0.0120 (6)0.0099 (5)0.0018 (4)0.0010 (4)0.0010 (4)
C150.0198 (6)0.0094 (5)0.0149 (6)0.0027 (4)0.0058 (5)0.0029 (4)
Cl150.03592 (18)0.00971 (13)0.01741 (15)0.00627 (12)0.00616 (13)0.00424 (11)
C160.0188 (6)0.0100 (5)0.0166 (6)0.0008 (4)0.0038 (5)0.0026 (4)
C170.0157 (6)0.0137 (6)0.0114 (5)0.0006 (4)0.0008 (4)0.0024 (4)
Cl170.03090 (17)0.01686 (15)0.01538 (15)0.00224 (12)0.00924 (12)0.00640 (11)
C17A0.0135 (5)0.0100 (5)0.0104 (5)0.0008 (4)0.0013 (4)0.0004 (4)
C210.0152 (5)0.0108 (5)0.0080 (5)0.0015 (4)0.0017 (4)0.0004 (4)
C220.0147 (5)0.0106 (5)0.0075 (5)0.0016 (4)0.0016 (4)0.0009 (4)
N240.0133 (5)0.0133 (5)0.0077 (4)0.0004 (4)0.0015 (4)0.0000 (4)
C250.0167 (6)0.0202 (6)0.0125 (5)0.0001 (5)0.0030 (5)0.0003 (5)
C260.0152 (6)0.0213 (6)0.0171 (6)0.0007 (5)0.0010 (5)0.0014 (5)
C270.0150 (6)0.0207 (6)0.0126 (5)0.0027 (5)0.0020 (4)0.0018 (5)
C27A0.0150 (5)0.0122 (5)0.0080 (5)0.0003 (4)0.0030 (4)0.0006 (4)
C2170.0170 (6)0.0136 (6)0.0094 (5)0.0002 (4)0.0001 (4)0.0008 (4)
O2170.0293 (5)0.0226 (5)0.0159 (4)0.0116 (4)0.0029 (4)0.0053 (4)
C2110.0143 (5)0.0152 (6)0.0077 (5)0.0018 (4)0.0011 (4)0.0001 (4)
C2120.0212 (6)0.0158 (6)0.0105 (5)0.0012 (5)0.0012 (5)0.0012 (4)
C2130.0222 (6)0.0162 (6)0.0138 (6)0.0004 (5)0.0017 (5)0.0028 (5)
C2140.0149 (6)0.0215 (6)0.0096 (5)0.0053 (5)0.0023 (4)0.0037 (5)
Cl140.02718 (17)0.02621 (17)0.01487 (14)0.00592 (13)0.01070 (12)0.00483 (12)
C2150.0192 (6)0.0194 (6)0.0105 (5)0.0054 (5)0.0001 (5)0.0025 (5)
C2160.0191 (6)0.0157 (6)0.0110 (5)0.0008 (5)0.0011 (5)0.0007 (4)
C2270.0161 (6)0.0137 (6)0.0093 (5)0.0020 (4)0.0007 (4)0.0026 (4)
O2270.0211 (5)0.0178 (4)0.0163 (4)0.0004 (4)0.0004 (4)0.0044 (4)
C2210.0143 (6)0.0186 (6)0.0119 (5)0.0027 (5)0.0022 (4)0.0004 (5)
C2220.0166 (6)0.0197 (6)0.0233 (6)0.0039 (5)0.0044 (5)0.0027 (5)
C2230.0188 (6)0.0264 (7)0.0280 (7)0.0088 (5)0.0072 (6)0.0108 (6)
C2240.0133 (6)0.0401 (8)0.0179 (6)0.0075 (6)0.0029 (5)0.0109 (6)
Cl240.01454 (15)0.0578 (3)0.03092 (19)0.00889 (16)0.00122 (13)0.02106 (18)
C2250.0160 (6)0.0341 (8)0.0217 (7)0.0030 (6)0.0003 (5)0.0035 (6)
C2260.0180 (6)0.0218 (7)0.0184 (6)0.0004 (5)0.0013 (5)0.0015 (5)
C310.0174 (14)0.0201 (8)0.0238 (11)0.004 (2)0.0020 (8)0.0029 (14)
Cl310.0493 (9)0.0322 (5)0.0562 (6)0.0023 (5)0.0317 (6)0.0035 (5)
Cl320.0686 (15)0.0170 (5)0.0189 (5)0.0106 (8)0.0073 (6)0.0005 (3)
C410.0174 (14)0.0201 (8)0.0238 (11)0.004 (2)0.0020 (8)0.0029 (14)
Cl410.078 (3)0.0434 (11)0.0296 (10)0.0187 (17)0.0146 (16)0.0091 (7)
Cl420.041 (3)0.022 (3)0.048 (3)0.014 (2)0.032 (3)0.008 (3)
C510.0174 (14)0.0201 (8)0.0238 (11)0.004 (2)0.0020 (8)0.0029 (14)
Cl510.078 (3)0.0434 (11)0.0296 (10)0.0187 (17)0.0146 (16)0.0091 (7)
Cl520.041 (3)0.022 (3)0.048 (3)0.014 (2)0.032 (3)0.008 (3)
Geometric parameters (Å, º) top
N11—C121.3577 (15)C217—C2111.4988 (16)
N11—C17A1.4039 (16)C211—C2121.3969 (18)
N11—H110.852 (17)C211—C2161.4015 (17)
C12—O121.2261 (15)C212—C2131.3941 (17)
C12—C131.5572 (16)C212—H2120.9500
C13—N241.4633 (15)C213—C2141.3859 (18)
C13—C13A1.5298 (17)C213—H2130.9500
C13—C221.5622 (16)C214—C2151.3877 (19)
C13A—C141.3858 (17)C214—Cl141.7445 (13)
C13A—C17A1.3977 (16)C215—C2161.3896 (17)
C14—C151.3963 (17)C215—H2150.9500
C14—H140.9500C216—H2160.9500
C15—C161.3907 (18)C227—O2271.2197 (16)
C15—Cl151.7398 (13)C227—C2211.4964 (17)
C16—C171.3923 (18)C221—C2221.3989 (19)
C16—H160.9500C221—C2261.4003 (19)
C17—C17A1.3847 (17)C222—C2231.3922 (19)
C17—Cl171.7361 (13)C222—H2220.9500
C21—C2171.5260 (16)C223—C2241.385 (2)
C21—C221.5293 (16)C223—H2230.9500
C21—C27A1.5453 (17)C224—C2251.388 (2)
C21—H211.0000C224—Cl241.7462 (14)
C22—C2271.5225 (17)C225—C2261.3926 (19)
C22—H221.0000C225—H2250.9500
N24—C251.4797 (16)C226—H2260.9500
N24—C27A1.4951 (15)C31—Cl321.758 (2)
C25—C261.5372 (17)C31—Cl311.761 (3)
C25—H25A0.9900C31—H31A0.9900
C25—H25B0.9900C31—H31B0.9900
C26—C271.5377 (18)C41—Cl421.758 (4)
C26—H26A0.9900C41—Cl411.761 (5)
C26—H26B0.9900C41—H41B0.9900
C27—C27A1.5276 (17)C41—H41A0.9900
C27—H27B0.9900C51—Cl521.758 (4)
C27—H27C0.9900C51—Cl511.763 (5)
C27A—H27A1.0000C51—H51B0.9900
C217—O2171.2185 (16)C51—H51A0.9900
C12—N11—C17A110.93 (10)C27—C27A—C21120.22 (10)
C12—N11—H11123.3 (11)N24—C27A—H27A108.6
C17A—N11—H11125.4 (11)C27—C27A—H27A108.6
O12—C12—N11125.93 (11)C21—C27A—H27A108.6
O12—C12—C13125.17 (10)O217—C217—C211120.71 (11)
N11—C12—C13108.90 (10)O217—C217—C21121.15 (11)
N24—C13—C13A118.30 (10)C211—C217—C21117.96 (10)
N24—C13—C12110.49 (9)C212—C211—C216119.03 (11)
C13A—C13—C12101.30 (9)C212—C211—C217122.77 (11)
N24—C13—C22101.06 (9)C216—C211—C217118.20 (11)
C13A—C13—C22114.92 (10)C213—C212—C211120.68 (12)
C12—C13—C22111.02 (9)C213—C212—H212119.7
C14—C13A—C17A120.02 (11)C211—C212—H212119.7
C14—C13A—C13131.99 (11)C214—C213—C212118.82 (12)
C17A—C13A—C13107.98 (10)C214—C213—H213120.6
C13A—C14—C15118.00 (11)C212—C213—H213120.6
C13A—C14—H14121.0C213—C214—C215121.84 (11)
C15—C14—H14121.0C213—C214—Cl14119.05 (10)
C16—C15—C14122.43 (11)C215—C214—Cl14119.11 (10)
C16—C15—Cl15119.10 (10)C214—C215—C216118.78 (12)
C14—C15—Cl15118.46 (10)C214—C215—H215120.6
C15—C16—C17118.89 (11)C216—C215—H215120.6
C15—C16—H16120.6C215—C216—C211120.78 (12)
C17—C16—H16120.6C215—C216—H216119.6
C17A—C17—C16119.24 (11)C211—C216—H216119.6
C17A—C17—Cl17119.66 (9)O227—C227—C221121.57 (12)
C16—C17—Cl17121.06 (9)O227—C227—C22121.09 (11)
C17—C17A—C13A121.40 (11)C221—C227—C22117.28 (10)
C17—C17A—N11127.70 (11)C222—C221—C226119.72 (12)
C13A—C17A—N11110.88 (10)C222—C221—C227121.79 (12)
C217—C21—C22112.96 (10)C226—C221—C227118.47 (12)
C217—C21—C27A109.63 (10)C223—C222—C221120.21 (13)
C22—C21—C27A102.92 (9)C223—C222—H222119.9
C217—C21—H21110.4C221—C222—H222119.9
C22—C21—H21110.4C224—C223—C222119.08 (13)
C27A—C21—H21110.4C224—C223—H223120.5
C227—C22—C21115.02 (10)C222—C223—H223120.5
C227—C22—C13113.03 (9)C223—C224—C225121.83 (13)
C21—C22—C13102.68 (9)C223—C224—Cl24118.69 (12)
C227—C22—H22108.6C225—C224—Cl24119.47 (12)
C21—C22—H22108.6C224—C225—C226118.99 (13)
C13—C22—H22108.6C224—C225—H225120.5
C13—N24—C25119.75 (10)C226—C225—H225120.5
C13—N24—C27A110.37 (9)C225—C226—C221120.16 (13)
C25—N24—C27A109.10 (9)C225—C226—H226119.9
N24—C25—C26103.69 (10)C221—C226—H226119.9
N24—C25—H25A111.0Cl32—C31—Cl31110.93 (18)
C26—C25—H25A111.0Cl32—C31—H31A109.5
N24—C25—H25B111.0Cl31—C31—H31A109.5
C26—C25—H25B111.0Cl32—C31—H31B109.5
H25A—C25—H25B109.0Cl31—C31—H31B109.5
C25—C26—C27102.41 (10)H31A—C31—H31B108.0
C25—C26—H26A111.3Cl42—C41—Cl41112.0 (5)
C27—C26—H26A111.3Cl42—C41—H41B109.2
C25—C26—H26B111.3Cl41—C41—H41B109.2
C27—C26—H26B111.3Cl42—C41—H41A109.2
H26A—C26—H26B109.2Cl41—C41—H41A109.2
C27A—C27—C26101.04 (10)H41B—C41—H41A107.9
C27A—C27—H27B111.6Cl52—C51—Cl51112.2 (4)
C26—C27—H27B111.6Cl52—C51—H51B109.2
C27A—C27—H27C111.6Cl51—C51—H51B109.2
C26—C27—H27C111.6Cl52—C51—H51A109.2
H27B—C27—H27C109.4Cl51—C51—H51A109.2
N24—C27A—C27105.09 (10)H51B—C51—H51A107.9
N24—C27A—C21105.08 (9)
C17A—N11—C12—O12179.26 (12)C27A—N24—C25—C2615.32 (13)
C17A—N11—C12—C130.25 (14)N24—C25—C26—C2736.26 (12)
O12—C12—C13—N2454.83 (16)C25—C26—C27—C27A42.92 (12)
N11—C12—C13—N24125.66 (11)C13—N24—C27A—C27121.73 (11)
O12—C12—C13—C13A178.96 (12)C25—N24—C27A—C2711.79 (12)
N11—C12—C13—C13A0.56 (12)C13—N24—C27A—C216.05 (12)
O12—C12—C13—C2256.46 (16)C25—N24—C27A—C21139.57 (10)
N11—C12—C13—C22123.05 (11)C26—C27—C27A—N2433.76 (12)
N24—C13—C13A—C1458.43 (18)C26—C27—C27A—C21151.72 (10)
C12—C13—C13A—C14179.30 (13)C217—C21—C27A—N24141.06 (10)
C22—C13—C13A—C1460.94 (17)C22—C21—C27A—N2420.61 (11)
N24—C13—C13A—C17A120.20 (11)C217—C21—C27A—C27100.97 (12)
C12—C13—C13A—C17A0.67 (12)C22—C21—C27A—C27138.58 (11)
C22—C13—C13A—C17A120.43 (11)C22—C21—C217—O21715.85 (17)
C17A—C13A—C14—C150.36 (18)C27A—C21—C217—O21798.29 (14)
C13—C13A—C14—C15178.86 (12)C22—C21—C217—C211168.99 (10)
C13A—C14—C15—C161.24 (19)C27A—C21—C217—C21176.86 (13)
C13A—C14—C15—Cl15179.66 (9)O217—C217—C211—C212157.38 (13)
C14—C15—C16—C170.74 (19)C21—C217—C211—C21227.44 (17)
Cl15—C15—C16—C17179.15 (10)O217—C217—C211—C21621.93 (18)
C15—C16—C17—C17A0.65 (18)C21—C217—C211—C216153.25 (11)
C15—C16—C17—Cl17176.92 (10)C216—C211—C212—C2132.22 (19)
C16—C17—C17A—C13A1.53 (18)C217—C211—C212—C213177.08 (12)
Cl17—C17—C17A—C13A176.08 (9)C211—C212—C213—C2141.8 (2)
C16—C17—C17A—N11179.64 (12)C212—C213—C214—C2150.5 (2)
Cl17—C17—C17A—N112.02 (18)C212—C213—C214—Cl14179.30 (10)
C14—C13A—C17A—C171.01 (18)C213—C214—C215—C2162.29 (19)
C13—C13A—C17A—C17177.81 (11)Cl14—C214—C215—C216177.56 (10)
C14—C13A—C17A—N11179.41 (11)C214—C215—C216—C2111.78 (19)
C13—C13A—C17A—N110.59 (14)C212—C211—C216—C2150.43 (19)
C12—N11—C17A—C17178.06 (12)C217—C211—C216—C215178.90 (11)
C12—N11—C17A—C13A0.22 (14)C21—C22—C227—O22719.59 (16)
C217—C21—C22—C22780.51 (13)C13—C22—C227—O22797.90 (13)
C27A—C21—C22—C227161.35 (10)C21—C22—C227—C221163.02 (10)
C217—C21—C22—C13156.29 (10)C13—C22—C227—C22179.49 (13)
C27A—C21—C22—C1338.15 (11)O227—C227—C221—C222152.22 (13)
N24—C13—C22—C227166.02 (9)C22—C227—C221—C22230.40 (17)
C13A—C13—C22—C22737.45 (13)O227—C227—C221—C22626.43 (18)
C12—C13—C22—C22776.76 (12)C22—C227—C221—C226150.95 (11)
N24—C13—C22—C2141.50 (11)C226—C221—C222—C2230.5 (2)
C13A—C13—C22—C2187.07 (11)C227—C221—C222—C223178.15 (12)
C12—C13—C22—C21158.72 (9)C221—C222—C223—C2240.4 (2)
C13A—C13—N24—C2530.89 (15)C222—C223—C224—C2250.1 (2)
C12—C13—N24—C2585.14 (13)C222—C223—C224—Cl24179.01 (11)
C22—C13—N24—C25157.26 (10)C223—C224—C225—C2260.5 (2)
C13A—C13—N24—C27A96.99 (12)Cl24—C224—C225—C226178.63 (11)
C12—C13—N24—C27A146.98 (10)C224—C225—C226—C2210.4 (2)
C22—C13—N24—C27A29.38 (11)C222—C221—C226—C2250.1 (2)
C13—N24—C25—C26143.79 (10)C227—C221—C226—C225178.57 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O12i0.852 (16)2.011 (16)2.8509 (17)168.8 (16)
C31—H31A···O120.992.383.192 (8)139
C31—H31A···N240.992.543.385 (12)144
C41—H41A···O120.992.243.06 (3)140
C41—H41A···N240.992.513.33 (4)140
C51—H51A···O120.992.292.912 (11)119
C51—H51A···N240.992.363.265 (12)151
Symmetry code: (i) x+1, y+1, z+1.
Selected geometric parameters (Å, °) top
(a) Ring-puckering parameters
Q2φ2
(I), ring 20.379 (4)92.8 (6)
(I), ring 30.388 (4)77.8 (6)
(II), ring 20.4160 (12)65.69 (17)
(II), ring 30.4257 (14)267.55 (17)
Ideal envelope36k
Ideal half-chair(36k + 18)
(b) Torsion angles
(I)(II)
H22—C22—C13—C13A145158
H21—C21—C22—H22-166-165
H21—C21—C27A—H27A156147
In both compounds, ring 1 (atoms N11/C12/C13/C13A/C17A) is planar. The puckering parameters are calculated for the atoms sequences N24–C13–C22–C21–C27A and N24–C25–C26–C27–C27A for rings 2 and 3, respectively. In the ideal values, k represents an integer.
Hydrogen bonds and short intermolecular contacts (Å, °) top
D—H···AD—HH···AD···AD—H···A
Compound (I)
O212—H212···O12i0.87 (3)1.79 (3)2.652 (3)176 (4)
C111—H11B···O227ii0.992.463.392 (4)157
C223—H223···O12iii0.952.563.452 (6)156
Compound (I)
N11—H11···O12ii0.852 (16)2.011 (16)2.8509 (17)168.8 (16)
C31—H31A···O120.992.383.192 (8)139
C31—H31A···N240.992.543.385 (12)144
C41—H41A···O120.992.243.06 (3)140
C41—H41A···N240.992.513.33 (4)140
C51—H51A···O120.992.292.912 (11)119
C51—H51A···N240.992.363.265 (12)151
Symmetry codes: (i) -y, -z, -x; (ii) -z+1, -x+1, -y+1; (iii) -x, -y, -z+1.
 

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