Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617016072/sk3676sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676IIsup3.hkl |
CCDC references: 1584355; 1584354
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).
C28H32N2O4 | Dx = 1.312 Mg m−3 |
Mr = 460.56 | Mo Kα radiation, λ = 0.71073 Å |
Rhombohedral, R3:R | Cell parameters from 5197 reflections |
a = 19.9182 (9) Å | θ = 2.4–27.2° |
α = 116.980 (2)° | µ = 0.09 mm−1 |
V = 3496.4 (11) Å3 | T = 100 K |
Z = 6 | Plate, colourless |
F(000) = 1476 | 0.27 × 0.21 × 0.13 mm |
Bruker D8 Venture diffractometer | 5194 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 3672 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.067 |
φ and ω scans | θmax = 27.2°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −25→24 |
Tmin = 0.959, Tmax = 0.989 | k = −21→25 |
35458 measured reflections | l = −25→25 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H 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 reflections | Δρmax = 0.59 e Å−3 |
311 parameters | Δρmin = −0.35 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
N11 | 0.28565 (15) | 0.30066 (15) | 0.64134 (15) | 0.0136 (3) | |
C12 | 0.18369 (18) | 0.17781 (18) | 0.50967 (18) | 0.0127 (4) | |
O12 | 0.06331 (12) | 0.08598 (13) | 0.42607 (12) | 0.0160 (3) | |
C13 | 0.24343 (18) | 0.17338 (18) | 0.48159 (18) | 0.0123 (4) | |
C13A | 0.39408 (18) | 0.30705 (18) | 0.62340 (18) | 0.0128 (4) | |
C14 | 0.50565 (19) | 0.36345 (19) | 0.67287 (19) | 0.0161 (4) | |
H14 | 0.4948 | 0.3144 | 0.6144 | 0.019* | |
C15 | 0.63468 (19) | 0.49387 (19) | 0.81038 (19) | 0.0188 (4) | |
H15 | 0.7121 | 0.5329 | 0.8462 | 0.023* | |
C16 | 0.65064 (19) | 0.56663 (19) | 0.89490 (19) | 0.0177 (4) | |
H16 | 0.7392 | 0.6564 | 0.9874 | 0.021* | |
C17 | 0.53910 (19) | 0.51055 (19) | 0.84676 (19) | 0.0164 (4) | |
H17 | 0.5497 | 0.5601 | 0.9045 | 0.020* | |
C17A | 0.41287 (18) | 0.38007 (18) | 0.71179 (18) | 0.0126 (4) | |
C21 | 0.17448 (18) | 0.00668 (18) | 0.31007 (18) | 0.0133 (4) | |
H21 | 0.2652 | 0.0647 | 0.3616 | 0.016* | |
C22 | 0.18358 (18) | 0.04304 (18) | 0.40260 (18) | 0.0124 (4) | |
H22 | 0.0898 | −0.0305 | 0.3451 | 0.015* | |
N24 | 0.19334 (16) | 0.15696 (16) | 0.38496 (15) | 0.0150 (3) | |
C25 | 0.2857 (2) | 0.2729 (2) | 0.4332 (2) | 0.0210 (5) | |
H25A | 0.3693 | 0.3579 | 0.5333 | 0.025* | |
H25B | 0.2418 | 0.2818 | 0.3983 | 0.025* | |
C26 | 0.3174 (2) | 0.2422 (2) | 0.3787 (2) | 0.0235 (5) | |
H26A | 0.3897 | 0.2670 | 0.4367 | 0.028* | |
H26B | 0.3445 | 0.2900 | 0.3704 | 0.028* | |
C27 | 0.1820 (2) | 0.0895 (2) | 0.2404 (2) | 0.0225 (5) | |
H27B | 0.1941 | 0.0489 | 0.2074 | 0.027* | |
H27C | 0.1191 | 0.0668 | 0.1732 | 0.027* | |
C27A | 0.1301 (2) | 0.04066 (19) | 0.26696 (19) | 0.0160 (4) | |
H27A | 0.0294 | −0.0382 | 0.1864 | 0.019* | |
C111 | 0.26698 (19) | 0.3384 (2) | 0.70535 (19) | 0.0174 (4) | |
H11A | 0.1691 | 0.2668 | 0.6345 | 0.021* | |
H11B | 0.3108 | 0.4231 | 0.7519 | 0.021* | |
C112 | 0.3266 (2) | 0.3588 (2) | 0.8082 (2) | 0.0227 (5) | |
H11C | 0.3484 | 0.3228 | 0.7966 | 0.027* | |
H11D | 0.4124 | 0.4570 | 0.9005 | 0.027* | |
C113 | 0.2346 (2) | 0.2917 (2) | 0.7967 (2) | 0.0296 (5) | |
H11E | 0.1536 | 0.1926 | 0.7080 | 0.035* | |
H11F | 0.2827 | 0.3117 | 0.8674 | 0.035* | |
C114 | 0.1875 (2) | 0.3315 (2) | 0.8094 (2) | 0.0308 (5) | |
H11G | 0.1278 | 0.2996 | 0.7312 | 0.037* | |
H11H | 0.1329 | 0.2847 | 0.8051 | 0.037* | |
C115 | 0.2999 (2) | 0.4808 (2) | 0.9372 (2) | 0.0336 (6) | |
H11I | 0.3443 | 0.5268 | 0.9345 | 0.040* | |
H11J | 0.3683 | 0.5165 | 1.0156 | 0.040* | |
C116 | 0.2467 (3) | 0.5124 (3) | 0.9559 (3) | 0.0396 (6) | |
H11K | 0.1756 | 0.4730 | 0.8763 | 0.059* | |
H11L | 0.3211 | 0.6105 | 1.0366 | 0.059* | |
H11M | 0.2097 | 0.4735 | 0.9665 | 0.059* | |
C211 | 0.07168 (19) | −0.14083 (19) | 0.18908 (18) | 0.0151 (4) | |
O211 | −0.03088 (14) | −0.22926 (13) | 0.13510 (14) | 0.0254 (4) | |
O212 | 0.10475 (14) | −0.16276 (14) | 0.14691 (14) | 0.0220 (3) | |
H212 | 0.041 (2) | −0.249 (2) | 0.076 (2) | 0.026* | |
C227 | 0.26501 (18) | 0.06015 (17) | 0.49367 (18) | 0.0131 (4) | |
O227 | 0.33092 (13) | 0.06284 (13) | 0.50208 (13) | 0.0186 (3) | |
C221 | 0.26486 (19) | 0.07644 (18) | 0.57438 (19) | 0.0153 (4) | |
C222 | 0.1553 (2) | 0.01930 (19) | 0.5305 (2) | 0.0187 (4) | |
H222 | 0.0791 | −0.0285 | 0.4486 | 0.022* | |
C223 | 0.1567 (2) | 0.0318 (2) | 0.6057 (2) | 0.0240 (5) | |
H223 | 0.0807 | −0.0093 | 0.5743 | 0.029* | |
C224 | 0.2691 (2) | 0.1044 (2) | 0.7267 (2) | 0.0279 (5) | |
H224 | 0.2708 | 0.1143 | 0.7790 | 0.033* | |
C225 | 0.3787 (2) | 0.1625 (2) | 0.7715 (2) | 0.0279 (5) | |
H225 | 0.4560 | 0.2132 | 0.8552 | 0.033* | |
C226 | 0.3765 (2) | 0.1474 (2) | 0.6954 (2) | 0.0217 (5) | |
H226 | 0.4512 | 0.1855 | 0.7255 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0124 (8) | 0.0151 (8) | 0.0121 (8) | 0.0113 (7) | 0.0104 (7) | 0.0109 (7) |
C12 | 0.0154 (9) | 0.0153 (9) | 0.0126 (9) | 0.0132 (9) | 0.0116 (9) | 0.0127 (9) |
O12 | 0.0112 (6) | 0.0163 (7) | 0.0120 (6) | 0.0107 (6) | 0.0090 (6) | 0.0108 (6) |
C13 | 0.0136 (9) | 0.0141 (9) | 0.0126 (9) | 0.0118 (8) | 0.0111 (8) | 0.0115 (8) |
C13A | 0.0153 (9) | 0.0123 (9) | 0.0138 (9) | 0.0115 (8) | 0.0122 (8) | 0.0114 (8) |
C14 | 0.0174 (10) | 0.0150 (9) | 0.0184 (10) | 0.0138 (9) | 0.0155 (9) | 0.0136 (9) |
C15 | 0.0143 (9) | 0.0167 (10) | 0.0200 (10) | 0.0123 (9) | 0.0140 (9) | 0.0147 (9) |
C16 | 0.0127 (9) | 0.0116 (9) | 0.0144 (9) | 0.0087 (9) | 0.0098 (9) | 0.0097 (9) |
C17 | 0.0177 (10) | 0.0143 (9) | 0.0149 (9) | 0.0132 (9) | 0.0134 (9) | 0.0117 (9) |
C17A | 0.0128 (9) | 0.0144 (9) | 0.0148 (9) | 0.0116 (8) | 0.0114 (8) | 0.0129 (8) |
C21 | 0.0120 (9) | 0.0124 (9) | 0.0110 (9) | 0.0096 (8) | 0.0096 (8) | 0.0090 (8) |
C22 | 0.0102 (9) | 0.0090 (8) | 0.0099 (9) | 0.0071 (8) | 0.0078 (8) | 0.0070 (8) |
N24 | 0.0203 (8) | 0.0173 (8) | 0.0146 (8) | 0.0162 (8) | 0.0151 (8) | 0.0141 (7) |
C25 | 0.0319 (11) | 0.0234 (10) | 0.0246 (11) | 0.0244 (10) | 0.0248 (10) | 0.0217 (10) |
C26 | 0.0353 (12) | 0.0276 (11) | 0.0328 (12) | 0.0276 (11) | 0.0309 (11) | 0.0278 (11) |
C27 | 0.0357 (12) | 0.0288 (11) | 0.0243 (11) | 0.0286 (11) | 0.0271 (11) | 0.0239 (10) |
C27A | 0.0178 (9) | 0.0170 (9) | 0.0130 (9) | 0.0146 (9) | 0.0126 (9) | 0.0125 (9) |
C111 | 0.0164 (9) | 0.0185 (10) | 0.0152 (9) | 0.0149 (9) | 0.0134 (9) | 0.0128 (9) |
C112 | 0.0263 (11) | 0.0272 (11) | 0.0237 (11) | 0.0228 (10) | 0.0221 (10) | 0.0217 (10) |
C113 | 0.0258 (12) | 0.0280 (12) | 0.0225 (11) | 0.0203 (11) | 0.0202 (11) | 0.0197 (11) |
C114 | 0.0310 (12) | 0.0347 (13) | 0.0313 (12) | 0.0267 (12) | 0.0272 (11) | 0.0279 (12) |
C115 | 0.0288 (12) | 0.0330 (13) | 0.0324 (13) | 0.0243 (12) | 0.0244 (12) | 0.0278 (12) |
C116 | 0.0353 (14) | 0.0413 (14) | 0.0438 (15) | 0.0325 (13) | 0.0336 (13) | 0.0343 (14) |
C211 | 0.0154 (9) | 0.0147 (9) | 0.0125 (9) | 0.0122 (9) | 0.0113 (8) | 0.0110 (8) |
O211 | 0.0171 (7) | 0.0137 (7) | 0.0214 (7) | 0.0102 (7) | 0.0157 (7) | 0.0109 (7) |
O212 | 0.0192 (7) | 0.0111 (7) | 0.0173 (7) | 0.0104 (6) | 0.0156 (7) | 0.0086 (6) |
C227 | 0.0108 (9) | 0.0073 (8) | 0.0100 (9) | 0.0064 (8) | 0.0075 (8) | 0.0063 (8) |
O227 | 0.0200 (7) | 0.0210 (7) | 0.0205 (7) | 0.0178 (7) | 0.0173 (7) | 0.0174 (7) |
C221 | 0.0171 (9) | 0.0124 (9) | 0.0155 (9) | 0.0119 (9) | 0.0133 (9) | 0.0119 (9) |
C222 | 0.0181 (10) | 0.0168 (10) | 0.0191 (10) | 0.0138 (9) | 0.0153 (9) | 0.0151 (9) |
C223 | 0.0269 (11) | 0.0244 (11) | 0.0303 (11) | 0.0211 (10) | 0.0256 (11) | 0.0236 (10) |
C224 | 0.0358 (12) | 0.0290 (12) | 0.0269 (11) | 0.0257 (11) | 0.0278 (11) | 0.0247 (11) |
C225 | 0.0272 (12) | 0.0308 (12) | 0.0203 (11) | 0.0228 (11) | 0.0190 (10) | 0.0217 (11) |
C226 | 0.0208 (10) | 0.0241 (11) | 0.0190 (10) | 0.0185 (10) | 0.0164 (10) | 0.0179 (10) |
N11—C12 | 1.351 (2) | C27A—H27A | 1.0000 |
N11—C17A | 1.419 (2) | C111—C112 | 1.540 (3) |
N11—C111 | 1.464 (2) | C111—H11A | 0.9900 |
C12—O12 | 1.225 (2) | C111—H11B | 0.9900 |
C12—C13 | 1.546 (3) | C112—C113 | 1.521 (3) |
C13—N24 | 1.482 (2) | C112—H11C | 0.9900 |
C13—C13A | 1.519 (3) | C112—H11D | 0.9900 |
C13—C22 | 1.556 (3) | C113—C114 | 1.511 (3) |
C13A—C14 | 1.384 (3) | C113—H11E | 0.9900 |
C13A—C17A | 1.393 (3) | C113—H11F | 0.9900 |
C14—C15 | 1.398 (3) | C114—C115 | 1.502 (3) |
C14—H14 | 0.9500 | C114—H11G | 0.9900 |
C15—C16 | 1.385 (3) | C114—H11H | 0.9900 |
C15—H15 | 0.9500 | C115—C116 | 1.551 (3) |
C16—C17 | 1.395 (3) | C115—H11I | 0.9900 |
C16—H16 | 0.9500 | C115—H11J | 0.9900 |
C17—C17A | 1.379 (3) | C116—H11K | 0.9800 |
C17—H17 | 0.9500 | C116—H11L | 0.9800 |
C21—C211 | 1.507 (3) | C116—H11M | 0.9800 |
C21—C22 | 1.524 (3) | C211—O211 | 1.206 (2) |
C21—C27A | 1.536 (3) | C211—O212 | 1.327 (2) |
C21—H21 | 1.0000 | O212—H212 | 0.87 (2) |
C22—C227 | 1.518 (3) | C227—O227 | 1.218 (2) |
C22—H22 | 1.0000 | C227—C221 | 1.490 (3) |
N24—C25 | 1.472 (3) | C221—C222 | 1.392 (3) |
N24—C27A | 1.484 (2) | C221—C226 | 1.395 (3) |
C25—C26 | 1.525 (3) | C222—C223 | 1.387 (3) |
C25—H25A | 0.9900 | C222—H222 | 0.9500 |
C25—H25B | 0.9900 | C223—C224 | 1.385 (3) |
C26—C27 | 1.526 (3) | C223—H223 | 0.9500 |
C26—H26A | 0.9900 | C224—C225 | 1.378 (3) |
C26—H26B | 0.9900 | C224—H224 | 0.9500 |
C27—C27A | 1.532 (3) | C225—C226 | 1.382 (3) |
C27—H27B | 0.9900 | C225—H225 | 0.9500 |
C27—H27C | 0.9900 | C226—H226 | 0.9500 |
C12—N11—C17A | 110.72 (15) | C27—C27A—C21 | 115.22 (16) |
C12—N11—C111 | 124.01 (16) | N24—C27A—H27A | 110.2 |
C17A—N11—C111 | 124.73 (15) | C27—C27A—H27A | 110.2 |
O12—C12—N11 | 125.14 (18) | C21—C27A—H27A | 110.2 |
O12—C12—C13 | 125.83 (17) | N11—C111—C112 | 112.56 (16) |
N11—C12—C13 | 109.01 (15) | N11—C111—H11A | 109.1 |
N24—C13—C13A | 116.59 (15) | C112—C111—H11A | 109.1 |
N24—C13—C12 | 107.28 (14) | N11—C111—H11B | 109.1 |
C13A—C13—C12 | 101.39 (14) | C112—C111—H11B | 109.1 |
N24—C13—C22 | 103.51 (14) | H11A—C111—H11B | 107.8 |
C13A—C13—C22 | 116.71 (15) | C113—C112—C111 | 114.72 (18) |
C12—C13—C22 | 111.19 (15) | C113—C112—H11C | 108.6 |
C14—C13A—C17A | 119.41 (17) | C111—C112—H11C | 108.6 |
C14—C13A—C13 | 132.13 (17) | C113—C112—H11D | 108.6 |
C17A—C13A—C13 | 108.44 (16) | C111—C112—H11D | 108.6 |
C13A—C14—C15 | 118.81 (18) | H11C—C112—H11D | 107.6 |
C13A—C14—H14 | 120.6 | C114—C113—C112 | 117.0 (2) |
C15—C14—H14 | 120.6 | C114—C113—H11E | 108.1 |
C16—C15—C14 | 120.59 (18) | C112—C113—H11E | 108.1 |
C16—C15—H15 | 119.7 | C114—C113—H11F | 108.1 |
C14—C15—H15 | 119.7 | C112—C113—H11F | 108.1 |
C15—C16—C17 | 121.21 (18) | H11E—C113—H11F | 107.3 |
C15—C16—H16 | 119.4 | C115—C114—C113 | 114.2 (2) |
C17—C16—H16 | 119.4 | C115—C114—H11G | 108.7 |
C17A—C17—C16 | 117.12 (18) | C113—C114—H11G | 108.7 |
C17A—C17—H17 | 121.4 | C115—C114—H11H | 108.7 |
C16—C17—H17 | 121.4 | C113—C114—H11H | 108.7 |
C17—C17A—C13A | 122.75 (17) | H11G—C114—H11H | 107.6 |
C17—C17A—N11 | 127.36 (17) | C114—C115—C116 | 111.5 (2) |
C13A—C17A—N11 | 109.89 (16) | C114—C115—H11I | 109.3 |
C211—C21—C22 | 112.18 (15) | C116—C115—H11I | 109.3 |
C211—C21—C27A | 110.95 (15) | C114—C115—H11J | 109.3 |
C22—C21—C27A | 102.12 (15) | C116—C115—H11J | 109.3 |
C211—C21—H21 | 110.4 | H11I—C115—H11J | 108.0 |
C22—C21—H21 | 110.4 | C115—C116—H11K | 109.5 |
C27A—C21—H21 | 110.4 | C115—C116—H11L | 109.5 |
C227—C22—C21 | 113.89 (15) | H11K—C116—H11L | 109.5 |
C227—C22—C13 | 113.48 (15) | C115—C116—H11M | 109.5 |
C21—C22—C13 | 104.09 (14) | H11K—C116—H11M | 109.5 |
C227—C22—H22 | 108.4 | H11L—C116—H11M | 109.5 |
C21—C22—H22 | 108.4 | O211—C211—O212 | 123.90 (18) |
C13—C22—H22 | 108.4 | O211—C211—C21 | 123.33 (17) |
C25—N24—C13 | 119.60 (15) | O212—C211—C21 | 112.75 (16) |
C25—N24—C27A | 108.43 (15) | C211—O212—H212 | 109.3 (15) |
C13—N24—C27A | 110.41 (14) | O227—C227—C221 | 120.88 (17) |
N24—C25—C26 | 105.22 (15) | O227—C227—C22 | 120.39 (17) |
N24—C25—H25A | 110.7 | C221—C227—C22 | 118.72 (16) |
C26—C25—H25A | 110.7 | C222—C221—C226 | 119.25 (18) |
N24—C25—H25B | 110.7 | C222—C221—C227 | 122.06 (17) |
C26—C25—H25B | 110.7 | C226—C221—C227 | 118.65 (18) |
H25A—C25—H25B | 108.8 | C223—C222—C221 | 120.28 (19) |
C25—C26—C27 | 101.68 (17) | C223—C222—H222 | 119.9 |
C25—C26—H26A | 111.4 | C221—C222—H222 | 119.9 |
C27—C26—H26A | 111.4 | C224—C223—C222 | 119.8 (2) |
C25—C26—H26B | 111.4 | C224—C223—H223 | 120.1 |
C27—C26—H26B | 111.4 | C222—C223—H223 | 120.1 |
H26A—C26—H26B | 109.3 | C225—C224—C223 | 120.2 (2) |
C26—C27—C27A | 103.40 (16) | C225—C224—H224 | 119.9 |
C26—C27—H27B | 111.1 | C223—C224—H224 | 119.9 |
C27A—C27—H27B | 111.1 | C224—C225—C226 | 120.3 (2) |
C26—C27—H27C | 111.1 | C224—C225—H225 | 119.8 |
C27A—C27—H27C | 111.1 | C226—C225—H225 | 119.8 |
H27B—C27—H27C | 109.0 | C225—C226—C221 | 120.1 (2) |
N24—C27A—C27 | 105.61 (15) | C225—C226—H226 | 120.0 |
N24—C27A—C21 | 105.07 (14) | C221—C226—H226 | 120.0 |
C17A—N11—C12—O12 | 176.43 (17) | C13A—C13—N24—C27A | 119.76 (17) |
C111—N11—C12—O12 | 4.5 (3) | C12—C13—N24—C27A | −127.47 (16) |
C17A—N11—C12—C13 | −4.7 (2) | C22—C13—N24—C27A | −9.83 (18) |
C111—N11—C12—C13 | −176.63 (16) | C13—N24—C25—C26 | 106.85 (19) |
O12—C12—C13—N24 | 63.1 (2) | C27A—N24—C25—C26 | −20.9 (2) |
N11—C12—C13—N24 | −115.74 (16) | N24—C25—C26—C27 | 36.7 (2) |
O12—C12—C13—C13A | −174.14 (18) | C25—C26—C27—C27A | −38.3 (2) |
N11—C12—C13—C13A | 7.00 (19) | C25—N24—C27A—C27 | −3.6 (2) |
O12—C12—C13—C22 | −49.4 (2) | C13—N24—C27A—C27 | −136.37 (16) |
N11—C12—C13—C22 | 131.74 (16) | C25—N24—C27A—C21 | 118.67 (16) |
N24—C13—C13A—C14 | −69.0 (3) | C13—N24—C27A—C21 | −14.13 (19) |
C12—C13—C13A—C14 | 174.9 (2) | C26—C27—C27A—N24 | 26.4 (2) |
C22—C13—C13A—C14 | 53.9 (3) | C26—C27—C27A—C21 | −89.02 (19) |
N24—C13—C13A—C17A | 109.22 (18) | C211—C21—C27A—N24 | 152.19 (15) |
C12—C13—C13A—C17A | −6.86 (19) | C22—C21—C27A—N24 | 32.47 (18) |
C22—C13—C13A—C17A | −127.80 (17) | C211—C21—C27A—C27 | −92.03 (19) |
C17A—C13A—C14—C15 | −1.3 (3) | C22—C21—C27A—C27 | 148.25 (16) |
C13—C13A—C14—C15 | 176.82 (19) | C12—N11—C111—C112 | 111.4 (2) |
C13A—C14—C15—C16 | −1.6 (3) | C17A—N11—C111—C112 | −59.4 (2) |
C14—C15—C16—C17 | 2.3 (3) | N11—C111—C112—C113 | −134.04 (19) |
C15—C16—C17—C17A | −0.1 (3) | C111—C112—C113—C114 | −57.4 (3) |
C16—C17—C17A—C13A | −2.9 (3) | C112—C113—C114—C115 | −55.4 (3) |
C16—C17—C17A—N11 | 177.67 (18) | C113—C114—C115—C116 | −170.0 (2) |
C14—C13A—C17A—C17 | 3.7 (3) | C22—C21—C211—O211 | 33.0 (3) |
C13—C13A—C17A—C17 | −174.86 (17) | C27A—C21—C211—O211 | −80.5 (2) |
C14—C13A—C17A—N11 | −176.84 (16) | C22—C21—C211—O212 | −148.45 (16) |
C13—C13A—C17A—N11 | 4.6 (2) | C27A—C21—C211—O212 | 98.03 (19) |
C12—N11—C17A—C17 | 179.56 (18) | C21—C22—C227—O227 | 9.8 (2) |
C111—N11—C17A—C17 | −8.6 (3) | C13—C22—C227—O227 | −109.04 (19) |
C12—N11—C17A—C13A | 0.1 (2) | C21—C22—C227—C221 | −171.46 (15) |
C111—N11—C17A—C13A | 171.94 (17) | C13—C22—C227—C221 | 69.7 (2) |
C211—C21—C22—C227 | 78.58 (19) | O227—C227—C221—C222 | −151.83 (18) |
C27A—C21—C22—C227 | −162.57 (15) | C22—C227—C221—C222 | 29.5 (3) |
C211—C21—C22—C13 | −157.34 (15) | O227—C227—C221—C226 | 26.0 (3) |
C27A—C21—C22—C13 | −38.49 (17) | C22—C227—C221—C226 | −152.74 (17) |
N24—C13—C22—C227 | 154.56 (15) | C226—C221—C222—C223 | −0.6 (3) |
C13A—C13—C22—C227 | 25.0 (2) | C227—C221—C222—C223 | 177.16 (18) |
C12—C13—C22—C227 | −90.56 (18) | C221—C222—C223—C224 | 1.7 (3) |
N24—C13—C22—C21 | 30.21 (17) | C222—C223—C224—C225 | −1.0 (3) |
C13A—C13—C22—C21 | −99.30 (17) | C223—C224—C225—C226 | −0.8 (3) |
C12—C13—C22—C21 | 145.09 (15) | C224—C225—C226—C221 | 1.8 (3) |
C13A—C13—N24—C25 | −7.1 (2) | C222—C221—C226—C225 | −1.1 (3) |
C12—C13—N24—C25 | 105.71 (18) | C227—C221—C226—C225 | −178.98 (19) |
C22—C13—N24—C25 | −136.64 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O212—H212···O12i | 0.87 (3) | 1.79 (3) | 2.652 (3) | 176 (4) |
C111—H11B···O227ii | 0.99 | 2.46 | 3.392 (4) | 157 |
C223—H223···O12iii | 0.95 | 2.56 | 3.452 (6) | 156 |
Symmetry codes: (i) −y, −z, −x; (ii) −z+1, −x+1, −y+1; (iii) −x, −y, −z+1. |
C28H20Cl4N2O3·0.981CH2Cl2 | F(000) = 1340.8 |
Mr = 657.57 | Dx = 1.483 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.800 (4) Å | Cell parameters from 6780 reflections |
b = 12.511 (5) Å | θ = 2.2–27.5° |
c = 18.638 (5) Å | µ = 0.62 mm−1 |
β = 99.325 (12)° | T = 100 K |
V = 2945.3 (17) Å3 | Plate, colourless |
Z = 4 | 0.38 × 0.35 × 0.16 mm |
Bruker D8 Venture diffractometer | 6778 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 6162 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.031 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −16→16 |
Tmin = 0.889, Tmax = 0.910 | k = −16→16 |
92566 measured reflections | l = −24→24 |
Refinement on F2 | 9 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H 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 reflections | Δρmax = 0.48 e Å−3 |
397 parameters | Δρmin = −0.55 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N11 | 0.43284 (8) | 0.61892 (8) | 0.46172 (5) | 0.0123 (2) | |
H11 | 0.4751 (12) | 0.6057 (13) | 0.5009 (9) | 0.015* | |
C12 | 0.39675 (9) | 0.54291 (9) | 0.41183 (6) | 0.0114 (2) | |
O12 | 0.41299 (7) | 0.44655 (7) | 0.41841 (5) | 0.01519 (18) | |
C13 | 0.33169 (9) | 0.59797 (9) | 0.34400 (6) | 0.0107 (2) | |
C13A | 0.34080 (9) | 0.71562 (9) | 0.36652 (6) | 0.0113 (2) | |
C14 | 0.30039 (10) | 0.80815 (10) | 0.33166 (6) | 0.0136 (2) | |
H14 | 0.2593 | 0.8056 | 0.2844 | 0.016* | |
C15 | 0.32191 (10) | 0.90520 (10) | 0.36805 (7) | 0.0144 (2) | |
Cl15 | 0.27105 (3) | 1.02188 (2) | 0.32509 (2) | 0.02081 (8) | |
C16 | 0.38010 (10) | 0.91148 (10) | 0.43773 (7) | 0.0150 (2) | |
H16 | 0.3928 | 0.9786 | 0.4614 | 0.018* | |
C17 | 0.41944 (10) | 0.81773 (10) | 0.47228 (6) | 0.0139 (2) | |
Cl17 | 0.48725 (3) | 0.81961 (3) | 0.56084 (2) | 0.02249 (8) | |
C17A | 0.40057 (9) | 0.72119 (9) | 0.43617 (6) | 0.0114 (2) | |
C21 | 0.28396 (9) | 0.59190 (9) | 0.21334 (6) | 0.0118 (2) | |
H21 | 0.2772 | 0.6702 | 0.2030 | 0.014* | |
C22 | 0.37775 (9) | 0.57028 (9) | 0.27360 (6) | 0.0113 (2) | |
H22 | 0.3944 | 0.4922 | 0.2740 | 0.014* | |
N24 | 0.22596 (8) | 0.55076 (8) | 0.32714 (5) | 0.0118 (2) | |
C25 | 0.14005 (10) | 0.59019 (11) | 0.36463 (7) | 0.0164 (2) | |
H25A | 0.1539 | 0.6645 | 0.3819 | 0.020* | |
H25B | 0.1321 | 0.5441 | 0.4066 | 0.020* | |
C26 | 0.04113 (10) | 0.58455 (11) | 0.30572 (7) | 0.0180 (3) | |
H26A | −0.0137 | 0.6358 | 0.3157 | 0.022* | |
H26B | 0.0107 | 0.5116 | 0.3018 | 0.022* | |
C27 | 0.08530 (10) | 0.61535 (11) | 0.23659 (7) | 0.0166 (2) | |
H27B | 0.0371 | 0.5931 | 0.1921 | 0.020* | |
H27C | 0.0986 | 0.6932 | 0.2345 | 0.020* | |
C27A | 0.18843 (9) | 0.55161 (10) | 0.24688 (6) | 0.0123 (2) | |
H27A | 0.1722 | 0.4765 | 0.2303 | 0.015* | |
C217 | 0.29062 (10) | 0.53006 (10) | 0.14365 (6) | 0.0136 (2) | |
O217 | 0.35076 (8) | 0.45461 (8) | 0.14349 (5) | 0.0233 (2) | |
C211 | 0.21473 (9) | 0.55919 (10) | 0.07655 (6) | 0.0125 (2) | |
C212 | 0.17137 (10) | 0.66137 (10) | 0.06474 (7) | 0.0162 (2) | |
H212 | 0.1874 | 0.7146 | 0.1012 | 0.019* | |
C213 | 0.10482 (11) | 0.68601 (10) | 0.00000 (7) | 0.0179 (3) | |
H213 | 0.0770 | 0.7561 | −0.0085 | 0.021* | |
C214 | 0.08003 (10) | 0.60648 (11) | −0.05172 (7) | 0.0158 (2) | |
Cl14 | −0.00203 (3) | 0.63716 (3) | −0.13326 (2) | 0.02432 (8) | |
C215 | 0.11886 (10) | 0.50323 (11) | −0.04051 (7) | 0.0167 (2) | |
H215 | 0.0989 | 0.4491 | −0.0759 | 0.020* | |
C216 | 0.18744 (10) | 0.48039 (10) | 0.02338 (7) | 0.0154 (2) | |
H216 | 0.2162 | 0.4105 | 0.0311 | 0.018* | |
C227 | 0.47804 (10) | 0.63247 (10) | 0.26712 (6) | 0.0132 (2) | |
O227 | 0.47487 (7) | 0.71308 (7) | 0.23002 (5) | 0.01870 (19) | |
C221 | 0.57943 (10) | 0.59336 (10) | 0.31058 (7) | 0.0149 (2) | |
C222 | 0.59639 (11) | 0.48510 (11) | 0.32730 (8) | 0.0197 (3) | |
H222 | 0.5419 | 0.4346 | 0.3121 | 0.024* | |
C223 | 0.69288 (11) | 0.45120 (12) | 0.36608 (8) | 0.0240 (3) | |
H223 | 0.7048 | 0.3777 | 0.3773 | 0.029* | |
C224 | 0.77115 (11) | 0.52611 (13) | 0.38809 (7) | 0.0237 (3) | |
Cl24 | 0.89258 (3) | 0.48244 (4) | 0.43545 (2) | 0.03470 (10) | |
C225 | 0.75602 (11) | 0.63409 (13) | 0.37267 (8) | 0.0243 (3) | |
H225 | 0.8106 | 0.6843 | 0.3886 | 0.029* | |
C226 | 0.65967 (10) | 0.66774 (11) | 0.33350 (7) | 0.0196 (3) | |
H226 | 0.6483 | 0.7413 | 0.3223 | 0.023* | |
C31 | 0.2138 (3) | 0.2919 (10) | 0.37798 (18) | 0.0210 (5) | 0.615 (7) |
H31A | 0.2449 | 0.3646 | 0.3816 | 0.025* | 0.615 (7) |
H31B | 0.2700 | 0.2406 | 0.3977 | 0.025* | 0.615 (7) |
Cl31 | 0.1104 (2) | 0.28576 (13) | 0.42976 (12) | 0.0433 (5) | 0.615 (7) |
Cl32 | 0.1673 (2) | 0.2616 (2) | 0.28628 (10) | 0.0365 (5) | 0.615 (7) |
C41 | 0.2280 (10) | 0.293 (3) | 0.3719 (6) | 0.0210 (5) | 0.187 (5) |
H41A | 0.2652 | 0.3617 | 0.3687 | 0.025* | 0.187 (5) |
H41B | 0.2822 | 0.2360 | 0.3818 | 0.025* | 0.187 (5) |
Cl41 | 0.1552 (11) | 0.2985 (3) | 0.4443 (2) | 0.0498 (9) | 0.187 (5) |
Cl42 | 0.1467 (14) | 0.2669 (17) | 0.2883 (4) | 0.042 (2) | 0.187 (5) |
C51 | 0.2471 (8) | 0.2952 (10) | 0.3618 (3) | 0.0210 (5) | 0.179 (2) |
H51A | 0.2676 | 0.3687 | 0.3501 | 0.025* | 0.179 (2) |
H51B | 0.3061 | 0.2469 | 0.3553 | 0.025* | 0.179 (2) |
Cl51 | 0.2272 (4) | 0.2903 (2) | 0.45308 (15) | 0.0498 (9) | 0.179 (2) |
Cl52 | 0.1333 (12) | 0.2577 (16) | 0.3010 (4) | 0.042 (2) | 0.179 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0166 (5) | 0.0099 (5) | 0.0081 (4) | 0.0017 (4) | −0.0045 (4) | 0.0000 (4) |
C12 | 0.0133 (5) | 0.0118 (5) | 0.0083 (5) | 0.0001 (4) | −0.0011 (4) | 0.0004 (4) |
O12 | 0.0208 (4) | 0.0095 (4) | 0.0128 (4) | 0.0015 (3) | −0.0048 (3) | 0.0008 (3) |
C13 | 0.0136 (5) | 0.0090 (5) | 0.0082 (5) | 0.0010 (4) | −0.0021 (4) | 0.0008 (4) |
C13A | 0.0143 (5) | 0.0101 (5) | 0.0092 (5) | 0.0007 (4) | 0.0014 (4) | −0.0007 (4) |
C14 | 0.0185 (6) | 0.0120 (6) | 0.0099 (5) | 0.0018 (4) | 0.0010 (4) | 0.0010 (4) |
C15 | 0.0198 (6) | 0.0094 (5) | 0.0149 (6) | 0.0027 (4) | 0.0058 (5) | 0.0029 (4) |
Cl15 | 0.03592 (18) | 0.00971 (13) | 0.01741 (15) | 0.00627 (12) | 0.00616 (13) | 0.00424 (11) |
C16 | 0.0188 (6) | 0.0100 (5) | 0.0166 (6) | −0.0008 (4) | 0.0038 (5) | −0.0026 (4) |
C17 | 0.0157 (6) | 0.0137 (6) | 0.0114 (5) | −0.0006 (4) | −0.0008 (4) | −0.0024 (4) |
Cl17 | 0.03090 (17) | 0.01686 (15) | 0.01538 (15) | 0.00224 (12) | −0.00924 (12) | −0.00640 (11) |
C17A | 0.0135 (5) | 0.0100 (5) | 0.0104 (5) | 0.0008 (4) | 0.0013 (4) | 0.0004 (4) |
C21 | 0.0152 (5) | 0.0108 (5) | 0.0080 (5) | 0.0015 (4) | −0.0017 (4) | −0.0004 (4) |
C22 | 0.0147 (5) | 0.0106 (5) | 0.0075 (5) | 0.0016 (4) | −0.0016 (4) | −0.0009 (4) |
N24 | 0.0133 (5) | 0.0133 (5) | 0.0077 (4) | −0.0004 (4) | −0.0015 (4) | 0.0000 (4) |
C25 | 0.0167 (6) | 0.0202 (6) | 0.0125 (5) | 0.0001 (5) | 0.0030 (5) | 0.0003 (5) |
C26 | 0.0152 (6) | 0.0213 (6) | 0.0171 (6) | 0.0007 (5) | 0.0010 (5) | 0.0014 (5) |
C27 | 0.0150 (6) | 0.0207 (6) | 0.0126 (5) | 0.0027 (5) | −0.0020 (4) | 0.0018 (5) |
C27A | 0.0150 (5) | 0.0122 (5) | 0.0080 (5) | 0.0003 (4) | −0.0030 (4) | −0.0006 (4) |
C217 | 0.0170 (6) | 0.0136 (6) | 0.0094 (5) | −0.0002 (4) | −0.0001 (4) | −0.0008 (4) |
O217 | 0.0293 (5) | 0.0226 (5) | 0.0159 (4) | 0.0116 (4) | −0.0029 (4) | −0.0053 (4) |
C211 | 0.0143 (5) | 0.0152 (6) | 0.0077 (5) | −0.0018 (4) | 0.0011 (4) | 0.0001 (4) |
C212 | 0.0212 (6) | 0.0158 (6) | 0.0105 (5) | −0.0012 (5) | −0.0012 (5) | −0.0012 (4) |
C213 | 0.0222 (6) | 0.0162 (6) | 0.0138 (6) | 0.0004 (5) | −0.0017 (5) | 0.0028 (5) |
C214 | 0.0149 (6) | 0.0215 (6) | 0.0096 (5) | −0.0053 (5) | −0.0023 (4) | 0.0037 (5) |
Cl14 | 0.02718 (17) | 0.02621 (17) | 0.01487 (14) | −0.00592 (13) | −0.01070 (12) | 0.00483 (12) |
C215 | 0.0192 (6) | 0.0194 (6) | 0.0105 (5) | −0.0054 (5) | −0.0001 (5) | −0.0025 (5) |
C216 | 0.0191 (6) | 0.0157 (6) | 0.0110 (5) | −0.0008 (5) | 0.0011 (5) | −0.0007 (4) |
C227 | 0.0161 (6) | 0.0137 (6) | 0.0093 (5) | 0.0020 (4) | 0.0007 (4) | −0.0026 (4) |
O227 | 0.0211 (5) | 0.0178 (4) | 0.0163 (4) | −0.0004 (4) | 0.0004 (4) | 0.0044 (4) |
C221 | 0.0143 (6) | 0.0186 (6) | 0.0119 (5) | 0.0027 (5) | 0.0022 (4) | 0.0004 (5) |
C222 | 0.0166 (6) | 0.0197 (6) | 0.0233 (6) | 0.0039 (5) | 0.0044 (5) | 0.0027 (5) |
C223 | 0.0188 (6) | 0.0264 (7) | 0.0280 (7) | 0.0088 (5) | 0.0072 (6) | 0.0108 (6) |
C224 | 0.0133 (6) | 0.0401 (8) | 0.0179 (6) | 0.0075 (6) | 0.0029 (5) | 0.0109 (6) |
Cl24 | 0.01454 (15) | 0.0578 (3) | 0.03092 (19) | 0.00889 (16) | 0.00122 (13) | 0.02106 (18) |
C225 | 0.0160 (6) | 0.0341 (8) | 0.0217 (7) | −0.0030 (6) | −0.0003 (5) | 0.0035 (6) |
C226 | 0.0180 (6) | 0.0218 (7) | 0.0184 (6) | −0.0004 (5) | 0.0013 (5) | 0.0015 (5) |
C31 | 0.0174 (14) | 0.0201 (8) | 0.0238 (11) | −0.004 (2) | −0.0020 (8) | −0.0029 (14) |
Cl31 | 0.0493 (9) | 0.0322 (5) | 0.0562 (6) | 0.0023 (5) | 0.0317 (6) | 0.0035 (5) |
Cl32 | 0.0686 (15) | 0.0170 (5) | 0.0189 (5) | 0.0106 (8) | −0.0073 (6) | 0.0005 (3) |
C41 | 0.0174 (14) | 0.0201 (8) | 0.0238 (11) | −0.004 (2) | −0.0020 (8) | −0.0029 (14) |
Cl41 | 0.078 (3) | 0.0434 (11) | 0.0296 (10) | −0.0187 (17) | 0.0146 (16) | 0.0091 (7) |
Cl42 | 0.041 (3) | 0.022 (3) | 0.048 (3) | −0.014 (2) | −0.032 (3) | 0.008 (3) |
C51 | 0.0174 (14) | 0.0201 (8) | 0.0238 (11) | −0.004 (2) | −0.0020 (8) | −0.0029 (14) |
Cl51 | 0.078 (3) | 0.0434 (11) | 0.0296 (10) | −0.0187 (17) | 0.0146 (16) | 0.0091 (7) |
Cl52 | 0.041 (3) | 0.022 (3) | 0.048 (3) | −0.014 (2) | −0.032 (3) | 0.008 (3) |
N11—C12 | 1.3577 (15) | C217—C211 | 1.4988 (16) |
N11—C17A | 1.4039 (16) | C211—C212 | 1.3969 (18) |
N11—H11 | 0.852 (17) | C211—C216 | 1.4015 (17) |
C12—O12 | 1.2261 (15) | C212—C213 | 1.3941 (17) |
C12—C13 | 1.5572 (16) | C212—H212 | 0.9500 |
C13—N24 | 1.4633 (15) | C213—C214 | 1.3859 (18) |
C13—C13A | 1.5298 (17) | C213—H213 | 0.9500 |
C13—C22 | 1.5622 (16) | C214—C215 | 1.3877 (19) |
C13A—C14 | 1.3858 (17) | C214—Cl14 | 1.7445 (13) |
C13A—C17A | 1.3977 (16) | C215—C216 | 1.3896 (17) |
C14—C15 | 1.3963 (17) | C215—H215 | 0.9500 |
C14—H14 | 0.9500 | C216—H216 | 0.9500 |
C15—C16 | 1.3907 (18) | C227—O227 | 1.2197 (16) |
C15—Cl15 | 1.7398 (13) | C227—C221 | 1.4964 (17) |
C16—C17 | 1.3923 (18) | C221—C222 | 1.3989 (19) |
C16—H16 | 0.9500 | C221—C226 | 1.4003 (19) |
C17—C17A | 1.3847 (17) | C222—C223 | 1.3922 (19) |
C17—Cl17 | 1.7361 (13) | C222—H222 | 0.9500 |
C21—C217 | 1.5260 (16) | C223—C224 | 1.385 (2) |
C21—C22 | 1.5293 (16) | C223—H223 | 0.9500 |
C21—C27A | 1.5453 (17) | C224—C225 | 1.388 (2) |
C21—H21 | 1.0000 | C224—Cl24 | 1.7462 (14) |
C22—C227 | 1.5225 (17) | C225—C226 | 1.3926 (19) |
C22—H22 | 1.0000 | C225—H225 | 0.9500 |
N24—C25 | 1.4797 (16) | C226—H226 | 0.9500 |
N24—C27A | 1.4951 (15) | C31—Cl32 | 1.758 (2) |
C25—C26 | 1.5372 (17) | C31—Cl31 | 1.761 (3) |
C25—H25A | 0.9900 | C31—H31A | 0.9900 |
C25—H25B | 0.9900 | C31—H31B | 0.9900 |
C26—C27 | 1.5377 (18) | C41—Cl42 | 1.758 (4) |
C26—H26A | 0.9900 | C41—Cl41 | 1.761 (5) |
C26—H26B | 0.9900 | C41—H41B | 0.9900 |
C27—C27A | 1.5276 (17) | C41—H41A | 0.9900 |
C27—H27B | 0.9900 | C51—Cl52 | 1.758 (4) |
C27—H27C | 0.9900 | C51—Cl51 | 1.763 (5) |
C27A—H27A | 1.0000 | C51—H51B | 0.9900 |
C217—O217 | 1.2185 (16) | C51—H51A | 0.9900 |
C12—N11—C17A | 110.93 (10) | C27—C27A—C21 | 120.22 (10) |
C12—N11—H11 | 123.3 (11) | N24—C27A—H27A | 108.6 |
C17A—N11—H11 | 125.4 (11) | C27—C27A—H27A | 108.6 |
O12—C12—N11 | 125.93 (11) | C21—C27A—H27A | 108.6 |
O12—C12—C13 | 125.17 (10) | O217—C217—C211 | 120.71 (11) |
N11—C12—C13 | 108.90 (10) | O217—C217—C21 | 121.15 (11) |
N24—C13—C13A | 118.30 (10) | C211—C217—C21 | 117.96 (10) |
N24—C13—C12 | 110.49 (9) | C212—C211—C216 | 119.03 (11) |
C13A—C13—C12 | 101.30 (9) | C212—C211—C217 | 122.77 (11) |
N24—C13—C22 | 101.06 (9) | C216—C211—C217 | 118.20 (11) |
C13A—C13—C22 | 114.92 (10) | C213—C212—C211 | 120.68 (12) |
C12—C13—C22 | 111.02 (9) | C213—C212—H212 | 119.7 |
C14—C13A—C17A | 120.02 (11) | C211—C212—H212 | 119.7 |
C14—C13A—C13 | 131.99 (11) | C214—C213—C212 | 118.82 (12) |
C17A—C13A—C13 | 107.98 (10) | C214—C213—H213 | 120.6 |
C13A—C14—C15 | 118.00 (11) | C212—C213—H213 | 120.6 |
C13A—C14—H14 | 121.0 | C213—C214—C215 | 121.84 (11) |
C15—C14—H14 | 121.0 | C213—C214—Cl14 | 119.05 (10) |
C16—C15—C14 | 122.43 (11) | C215—C214—Cl14 | 119.11 (10) |
C16—C15—Cl15 | 119.10 (10) | C214—C215—C216 | 118.78 (12) |
C14—C15—Cl15 | 118.46 (10) | C214—C215—H215 | 120.6 |
C15—C16—C17 | 118.89 (11) | C216—C215—H215 | 120.6 |
C15—C16—H16 | 120.6 | C215—C216—C211 | 120.78 (12) |
C17—C16—H16 | 120.6 | C215—C216—H216 | 119.6 |
C17A—C17—C16 | 119.24 (11) | C211—C216—H216 | 119.6 |
C17A—C17—Cl17 | 119.66 (9) | O227—C227—C221 | 121.57 (12) |
C16—C17—Cl17 | 121.06 (9) | O227—C227—C22 | 121.09 (11) |
C17—C17A—C13A | 121.40 (11) | C221—C227—C22 | 117.28 (10) |
C17—C17A—N11 | 127.70 (11) | C222—C221—C226 | 119.72 (12) |
C13A—C17A—N11 | 110.88 (10) | C222—C221—C227 | 121.79 (12) |
C217—C21—C22 | 112.96 (10) | C226—C221—C227 | 118.47 (12) |
C217—C21—C27A | 109.63 (10) | C223—C222—C221 | 120.21 (13) |
C22—C21—C27A | 102.92 (9) | C223—C222—H222 | 119.9 |
C217—C21—H21 | 110.4 | C221—C222—H222 | 119.9 |
C22—C21—H21 | 110.4 | C224—C223—C222 | 119.08 (13) |
C27A—C21—H21 | 110.4 | C224—C223—H223 | 120.5 |
C227—C22—C21 | 115.02 (10) | C222—C223—H223 | 120.5 |
C227—C22—C13 | 113.03 (9) | C223—C224—C225 | 121.83 (13) |
C21—C22—C13 | 102.68 (9) | C223—C224—Cl24 | 118.69 (12) |
C227—C22—H22 | 108.6 | C225—C224—Cl24 | 119.47 (12) |
C21—C22—H22 | 108.6 | C224—C225—C226 | 118.99 (13) |
C13—C22—H22 | 108.6 | C224—C225—H225 | 120.5 |
C13—N24—C25 | 119.75 (10) | C226—C225—H225 | 120.5 |
C13—N24—C27A | 110.37 (9) | C225—C226—C221 | 120.16 (13) |
C25—N24—C27A | 109.10 (9) | C225—C226—H226 | 119.9 |
N24—C25—C26 | 103.69 (10) | C221—C226—H226 | 119.9 |
N24—C25—H25A | 111.0 | Cl32—C31—Cl31 | 110.93 (18) |
C26—C25—H25A | 111.0 | Cl32—C31—H31A | 109.5 |
N24—C25—H25B | 111.0 | Cl31—C31—H31A | 109.5 |
C26—C25—H25B | 111.0 | Cl32—C31—H31B | 109.5 |
H25A—C25—H25B | 109.0 | Cl31—C31—H31B | 109.5 |
C25—C26—C27 | 102.41 (10) | H31A—C31—H31B | 108.0 |
C25—C26—H26A | 111.3 | Cl42—C41—Cl41 | 112.0 (5) |
C27—C26—H26A | 111.3 | Cl42—C41—H41B | 109.2 |
C25—C26—H26B | 111.3 | Cl41—C41—H41B | 109.2 |
C27—C26—H26B | 111.3 | Cl42—C41—H41A | 109.2 |
H26A—C26—H26B | 109.2 | Cl41—C41—H41A | 109.2 |
C27A—C27—C26 | 101.04 (10) | H41B—C41—H41A | 107.9 |
C27A—C27—H27B | 111.6 | Cl52—C51—Cl51 | 112.2 (4) |
C26—C27—H27B | 111.6 | Cl52—C51—H51B | 109.2 |
C27A—C27—H27C | 111.6 | Cl51—C51—H51B | 109.2 |
C26—C27—H27C | 111.6 | Cl52—C51—H51A | 109.2 |
H27B—C27—H27C | 109.4 | Cl51—C51—H51A | 109.2 |
N24—C27A—C27 | 105.09 (10) | H51B—C51—H51A | 107.9 |
N24—C27A—C21 | 105.08 (9) | ||
C17A—N11—C12—O12 | 179.26 (12) | C27A—N24—C25—C26 | 15.32 (13) |
C17A—N11—C12—C13 | −0.25 (14) | N24—C25—C26—C27 | −36.26 (12) |
O12—C12—C13—N24 | 54.83 (16) | C25—C26—C27—C27A | 42.92 (12) |
N11—C12—C13—N24 | −125.66 (11) | C13—N24—C27A—C27 | −121.73 (11) |
O12—C12—C13—C13A | −178.96 (12) | C25—N24—C27A—C27 | 11.79 (12) |
N11—C12—C13—C13A | 0.56 (12) | C13—N24—C27A—C21 | 6.05 (12) |
O12—C12—C13—C22 | −56.46 (16) | C25—N24—C27A—C21 | 139.57 (10) |
N11—C12—C13—C22 | 123.05 (11) | C26—C27—C27A—N24 | −33.76 (12) |
N24—C13—C13A—C14 | −58.43 (18) | C26—C27—C27A—C21 | −151.72 (10) |
C12—C13—C13A—C14 | −179.30 (13) | C217—C21—C27A—N24 | 141.06 (10) |
C22—C13—C13A—C14 | 60.94 (17) | C22—C21—C27A—N24 | 20.61 (11) |
N24—C13—C13A—C17A | 120.20 (11) | C217—C21—C27A—C27 | −100.97 (12) |
C12—C13—C13A—C17A | −0.67 (12) | C22—C21—C27A—C27 | 138.58 (11) |
C22—C13—C13A—C17A | −120.43 (11) | C22—C21—C217—O217 | 15.85 (17) |
C17A—C13A—C14—C15 | 0.36 (18) | C27A—C21—C217—O217 | −98.29 (14) |
C13—C13A—C14—C15 | 178.86 (12) | C22—C21—C217—C211 | −168.99 (10) |
C13A—C14—C15—C16 | −1.24 (19) | C27A—C21—C217—C211 | 76.86 (13) |
C13A—C14—C15—Cl15 | −179.66 (9) | O217—C217—C211—C212 | −157.38 (13) |
C14—C15—C16—C17 | 0.74 (19) | C21—C217—C211—C212 | 27.44 (17) |
Cl15—C15—C16—C17 | 179.15 (10) | O217—C217—C211—C216 | 21.93 (18) |
C15—C16—C17—C17A | 0.65 (18) | C21—C217—C211—C216 | −153.25 (11) |
C15—C16—C17—Cl17 | −176.92 (10) | C216—C211—C212—C213 | −2.22 (19) |
C16—C17—C17A—C13A | −1.53 (18) | C217—C211—C212—C213 | 177.08 (12) |
Cl17—C17—C17A—C13A | 176.08 (9) | C211—C212—C213—C214 | 1.8 (2) |
C16—C17—C17A—N11 | −179.64 (12) | C212—C213—C214—C215 | 0.5 (2) |
Cl17—C17—C17A—N11 | −2.02 (18) | C212—C213—C214—Cl14 | −179.30 (10) |
C14—C13A—C17A—C17 | 1.01 (18) | C213—C214—C215—C216 | −2.29 (19) |
C13—C13A—C17A—C17 | −177.81 (11) | Cl14—C214—C215—C216 | 177.56 (10) |
C14—C13A—C17A—N11 | 179.41 (11) | C214—C215—C216—C211 | 1.78 (19) |
C13—C13A—C17A—N11 | 0.59 (14) | C212—C211—C216—C215 | 0.43 (19) |
C12—N11—C17A—C17 | 178.06 (12) | C217—C211—C216—C215 | −178.90 (11) |
C12—N11—C17A—C13A | −0.22 (14) | C21—C22—C227—O227 | 19.59 (16) |
C217—C21—C22—C227 | 80.51 (13) | C13—C22—C227—O227 | −97.90 (13) |
C27A—C21—C22—C227 | −161.35 (10) | C21—C22—C227—C221 | −163.02 (10) |
C217—C21—C22—C13 | −156.29 (10) | C13—C22—C227—C221 | 79.49 (13) |
C27A—C21—C22—C13 | −38.15 (11) | O227—C227—C221—C222 | −152.22 (13) |
N24—C13—C22—C227 | 166.02 (9) | C22—C227—C221—C222 | 30.40 (17) |
C13A—C13—C22—C227 | 37.45 (13) | O227—C227—C221—C226 | 26.43 (18) |
C12—C13—C22—C227 | −76.76 (12) | C22—C227—C221—C226 | −150.95 (11) |
N24—C13—C22—C21 | 41.50 (11) | C226—C221—C222—C223 | −0.5 (2) |
C13A—C13—C22—C21 | −87.07 (11) | C227—C221—C222—C223 | 178.15 (12) |
C12—C13—C22—C21 | 158.72 (9) | C221—C222—C223—C224 | 0.4 (2) |
C13A—C13—N24—C25 | −30.89 (15) | C222—C223—C224—C225 | 0.1 (2) |
C12—C13—N24—C25 | 85.14 (13) | C222—C223—C224—Cl24 | −179.01 (11) |
C22—C13—N24—C25 | −157.26 (10) | C223—C224—C225—C226 | −0.5 (2) |
C13A—C13—N24—C27A | 96.99 (12) | Cl24—C224—C225—C226 | 178.63 (11) |
C12—C13—N24—C27A | −146.98 (10) | C224—C225—C226—C221 | 0.4 (2) |
C22—C13—N24—C27A | −29.38 (11) | C222—C221—C226—C225 | 0.1 (2) |
C13—N24—C25—C26 | 143.79 (10) | C227—C221—C226—C225 | −178.57 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O12i | 0.852 (16) | 2.011 (16) | 2.8509 (17) | 168.8 (16) |
C31—H31A···O12 | 0.99 | 2.38 | 3.192 (8) | 139 |
C31—H31A···N24 | 0.99 | 2.54 | 3.385 (12) | 144 |
C41—H41A···O12 | 0.99 | 2.24 | 3.06 (3) | 140 |
C41—H41A···N24 | 0.99 | 2.51 | 3.33 (4) | 140 |
C51—H51A···O12 | 0.99 | 2.29 | 2.912 (11) | 119 |
C51—H51A···N24 | 0.99 | 2.36 | 3.265 (12) | 151 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
(a) Ring-puckering parameters | ||
Q2 | φ2 | |
(I), ring 2 | 0.379 (4) | 92.8 (6) |
(I), ring 3 | 0.388 (4) | 77.8 (6) |
(II), ring 2 | 0.4160 (12) | 65.69 (17) |
(II), ring 3 | 0.4257 (14) | 267.55 (17) |
Ideal envelope | 36k | |
Ideal half-chair | (36k + 18) | |
(b) Torsion angles | ||
(I) | (II) | |
H22—C22—C13—C13A | 145 | 158 |
H21—C21—C22—H22 | -166 | -165 |
H21—C21—C27A—H27A | 156 | 147 |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
Compound (I) | ||||
O212—H212···O12i | 0.87 (3) | 1.79 (3) | 2.652 (3) | 176 (4) |
C111—H11B···O227ii | 0.99 | 2.46 | 3.392 (4) | 157 |
C223—H223···O12iii | 0.95 | 2.56 | 3.452 (6) | 156 |
Compound (I) | ||||
N11—H11···O12ii | 0.852 (16) | 2.011 (16) | 2.8509 (17) | 168.8 (16) |
C31—H31A···O12 | 0.99 | 2.38 | 3.192 (8) | 139 |
C31—H31A···N24 | 0.99 | 2.54 | 3.385 (12) | 144 |
C41—H41A···O12 | 0.99 | 2.24 | 3.06 (3) | 140 |
C41—H41A···N24 | 0.99 | 2.51 | 3.33 (4) | 140 |
C51—H51A···O12 | 0.99 | 2.29 | 2.912 (11) | 119 |
C51—H51A···N24 | 0.99 | 2.36 | 3.265 (12) | 151 |
Symmetry codes: (i) -y, -z, -x; (ii) -z+1, -x+1, -y+1; (iii) -x, -y, -z+1. |
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