Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034921/cv2112sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034921/cv2112Isup2.hkl |
CCDC reference: 624188
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C19H22ClNO | F(000) = 1344 |
Mr = 315.83 | Dx = 1.218 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4258 reflections |
a = 9.8140 (16) Å | θ = 2.3–23.6° |
b = 32.640 (5) Å | µ = 0.22 mm−1 |
c = 10.7522 (18) Å | T = 120 K |
β = 91.276 (4)° | Prism, colourless |
V = 3443.3 (10) Å3 | 0.42 × 0.39 × 0.28 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 7885 independent reflections |
Radiation source: sealed tube | 4890 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.127 |
φ and ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −12→12 |
Tmin = 0.922, Tmax = 0.943 | k = −42→40 |
32978 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.091 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.256 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1172P)2 + 1.5681P] where P = (Fo2 + 2Fc2)/3 |
7885 reflections | (Δ/σ)max < 0.001 |
397 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.74 e Å−3 |
Experimental. IR (KBr) cm-1: 3251, 1667, 1610. 1H NMR (CDCl3) δ: 93 (6H, d, (CH3)2CH, J=6.6 Hz), 1.58 (3H, d, (ArCHCH3, J=7.2 Hz), 1.84–1.90 (1H, p, (ArCH3CH, J=6.9 Hz), 2.49 (2H, d, (CH3)2CHCH2Ar, J=7.2 Hz), 3.66–3.73 (1H, q, (CH3)2CH, J=6.9 Hz), 7.1–7.29 (5H, m, arom.), 7.74 (1H, s, arom.), 7.6 1H, s, arom.), 7.8 (2H, s, broad, NH). EIMS m/e: 295, 126, 119, 91, 64.9. Anal. Calcd. for C20H25NO C, 81.31; H, 8.53; N, 4.74; found C, 81.51; H, 8.47; N, 4.70 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.51744 (12) | 0.68426 (4) | −0.17248 (10) | 0.0426 (3) | |
O1 | 0.5965 (3) | 0.66863 (9) | 0.2863 (3) | 0.0324 (7) | |
N1 | 0.8137 (3) | 0.67556 (9) | 0.2246 (3) | 0.0228 (7) | |
H1A | 0.8997 | 0.6714 | 0.2461 | 0.027* | |
C101 | 0.7880 (4) | 0.69269 (11) | 0.1068 (3) | 0.0211 (8) | |
C102 | 0.6742 (4) | 0.68176 (11) | 0.0345 (3) | 0.0245 (8) | |
H10A | 0.6090 | 0.6630 | 0.0651 | 0.029* | |
C103 | 0.6581 (4) | 0.69870 (12) | −0.0821 (4) | 0.0271 (9) | |
C104 | 0.7493 (5) | 0.72636 (12) | −0.1293 (4) | 0.0342 (10) | |
H10B | 0.7346 | 0.7382 | −0.2092 | 0.041* | |
C105 | 0.8635 (4) | 0.73657 (12) | −0.0569 (4) | 0.0328 (10) | |
H10C | 0.9291 | 0.7550 | −0.0883 | 0.039* | |
C106 | 0.8819 (4) | 0.72003 (12) | 0.0599 (4) | 0.0281 (9) | |
H10H | 0.9598 | 0.7274 | 0.1090 | 0.034* | |
C107 | 0.7193 (4) | 0.66477 (11) | 0.3086 (3) | 0.0226 (8) | |
C108 | 0.7745 (4) | 0.64795 (12) | 0.4300 (3) | 0.0262 (8) | |
H10G | 0.8719 | 0.6567 | 0.4391 | 0.031* | |
C109 | 0.6970 (4) | 0.66582 (13) | 0.5391 (4) | 0.0323 (9) | |
H10D | 0.7027 | 0.6958 | 0.5370 | 0.048* | |
H10E | 0.7374 | 0.6557 | 0.6175 | 0.048* | |
H10F | 0.6013 | 0.6574 | 0.5329 | 0.048* | |
C110 | 0.7714 (4) | 0.60152 (12) | 0.4263 (3) | 0.0255 (8) | |
C111 | 0.8892 (4) | 0.57917 (13) | 0.4105 (4) | 0.0318 (9) | |
H11A | 0.9734 | 0.5931 | 0.4011 | 0.038* | |
C112 | 0.8862 (4) | 0.53704 (13) | 0.4084 (4) | 0.0346 (10) | |
H11B | 0.9688 | 0.5225 | 0.3969 | 0.041* | |
C113 | 0.7663 (4) | 0.51508 (12) | 0.4224 (4) | 0.0296 (9) | |
C114 | 0.6474 (4) | 0.53827 (13) | 0.4360 (4) | 0.0339 (10) | |
H11C | 0.5627 | 0.5246 | 0.4447 | 0.041* | |
C115 | 0.6501 (4) | 0.58013 (12) | 0.4370 (4) | 0.0309 (9) | |
H11D | 0.5674 | 0.5949 | 0.4453 | 0.037* | |
C116 | 0.7635 (5) | 0.46933 (13) | 0.4217 (4) | 0.0392 (10) | |
H11E | 0.7226 | 0.4598 | 0.4999 | 0.047* | |
H11F | 0.8585 | 0.4591 | 0.4209 | 0.047* | |
C117 | 0.6851 (5) | 0.45053 (13) | 0.3132 (5) | 0.0426 (11) | |
H11G | 0.5898 | 0.4613 | 0.3151 | 0.051* | |
C118 | 0.6780 (6) | 0.40378 (14) | 0.3256 (6) | 0.0610 (15) | |
H11H | 0.6273 | 0.3924 | 0.2541 | 0.092* | |
H11I | 0.6317 | 0.3966 | 0.4024 | 0.092* | |
H11J | 0.7705 | 0.3925 | 0.3282 | 0.092* | |
C119 | 0.7429 (7) | 0.46219 (16) | 0.1903 (5) | 0.0674 (17) | |
H11K | 0.7457 | 0.4921 | 0.1832 | 0.101* | |
H11L | 0.6855 | 0.4509 | 0.1229 | 0.101* | |
H11M | 0.8355 | 0.4512 | 0.1844 | 0.101* | |
Cl2 | 0.03076 (12) | 0.68778 (4) | 0.71905 (10) | 0.0420 (3) | |
O2 | 0.0979 (3) | 0.66789 (9) | 0.2629 (2) | 0.0319 (7) | |
N2 | 0.3169 (3) | 0.67405 (9) | 0.3301 (3) | 0.0233 (7) | |
H2A | 0.4023 | 0.6688 | 0.3124 | 0.028* | |
C201 | 0.2918 (4) | 0.69408 (11) | 0.4444 (3) | 0.0219 (8) | |
C202 | 0.1824 (4) | 0.68323 (11) | 0.5160 (3) | 0.0243 (8) | |
H20A | 0.1197 | 0.6628 | 0.4882 | 0.029* | |
C203 | 0.1663 (4) | 0.70243 (12) | 0.6278 (3) | 0.0272 (9) | |
C204 | 0.2535 (4) | 0.73258 (12) | 0.6707 (4) | 0.0324 (9) | |
H20B | 0.2384 | 0.7460 | 0.7476 | 0.039* | |
C205 | 0.3631 (4) | 0.74280 (12) | 0.5994 (4) | 0.0326 (9) | |
H20C | 0.4257 | 0.7631 | 0.6282 | 0.039* | |
C206 | 0.3831 (4) | 0.72382 (11) | 0.4856 (4) | 0.0269 (8) | |
H20H | 0.4586 | 0.7311 | 0.4365 | 0.032* | |
C207 | 0.2204 (4) | 0.66249 (11) | 0.2466 (3) | 0.0226 (8) | |
C208 | 0.2722 (4) | 0.64094 (12) | 0.1316 (4) | 0.0271 (9) | |
H20G | 0.3712 | 0.6475 | 0.1238 | 0.033* | |
C209 | 0.1976 (4) | 0.65616 (13) | 0.0147 (4) | 0.0357 (10) | |
H20D | 0.2328 | 0.6419 | −0.0582 | 0.054* | |
H20E | 0.2121 | 0.6857 | 0.0058 | 0.054* | |
H20F | 0.0999 | 0.6506 | 0.0213 | 0.054* | |
C210 | 0.2587 (4) | 0.59510 (12) | 0.1515 (3) | 0.0279 (9) | |
C211 | 0.3716 (4) | 0.57134 (14) | 0.1811 (4) | 0.0393 (11) | |
H21A | 0.4588 | 0.5839 | 0.1872 | 0.047* | |
C212 | 0.3605 (5) | 0.52975 (14) | 0.2021 (4) | 0.0426 (11) | |
H21B | 0.4399 | 0.5142 | 0.2222 | 0.051* | |
C213 | 0.2345 (5) | 0.51032 (13) | 0.1941 (4) | 0.0360 (10) | |
C214 | 0.1226 (4) | 0.53383 (13) | 0.1631 (4) | 0.0372 (10) | |
H21C | 0.0357 | 0.5211 | 0.1555 | 0.045* | |
C215 | 0.1336 (4) | 0.57533 (13) | 0.1428 (4) | 0.0358 (10) | |
H21D | 0.0540 | 0.5907 | 0.1224 | 0.043* | |
C216 | 0.2182 (6) | 0.46505 (14) | 0.2177 (4) | 0.0468 (12) | |
H21E | 0.1435 | 0.4611 | 0.2770 | 0.056* | |
H21F | 0.3031 | 0.4547 | 0.2580 | 0.056* | |
C217 | 0.1876 (5) | 0.43945 (13) | 0.1023 (4) | 0.0407 (11) | |
H21G | 0.1102 | 0.4527 | 0.0555 | 0.049* | |
C218 | 0.1438 (5) | 0.39659 (14) | 0.1371 (5) | 0.0549 (14) | |
H21H | 0.0649 | 0.3981 | 0.1911 | 0.082* | |
H21I | 0.2191 | 0.3827 | 0.1812 | 0.082* | |
H21J | 0.1193 | 0.3813 | 0.0615 | 0.082* | |
C219 | 0.3091 (7) | 0.43800 (17) | 0.0174 (6) | 0.0671 (17) | |
H21K | 0.3364 | 0.4660 | −0.0039 | 0.101* | |
H21L | 0.2842 | 0.4230 | −0.0588 | 0.101* | |
H21M | 0.3852 | 0.4241 | 0.0601 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0376 (6) | 0.0546 (7) | 0.0352 (6) | 0.0080 (5) | −0.0113 (5) | −0.0044 (5) |
O1 | 0.0115 (13) | 0.0497 (18) | 0.0361 (15) | 0.0007 (12) | 0.0022 (11) | 0.0067 (13) |
N1 | 0.0117 (15) | 0.0291 (18) | 0.0275 (16) | 0.0006 (13) | 0.0005 (12) | −0.0003 (13) |
C101 | 0.0168 (18) | 0.0187 (19) | 0.0278 (18) | 0.0050 (15) | 0.0015 (14) | −0.0016 (14) |
C102 | 0.0170 (18) | 0.024 (2) | 0.033 (2) | 0.0011 (15) | 0.0012 (15) | −0.0039 (15) |
C103 | 0.025 (2) | 0.027 (2) | 0.0294 (19) | 0.0111 (17) | −0.0026 (16) | −0.0053 (16) |
C104 | 0.045 (3) | 0.024 (2) | 0.034 (2) | 0.0094 (19) | 0.0035 (19) | 0.0051 (17) |
C105 | 0.039 (2) | 0.020 (2) | 0.040 (2) | −0.0009 (18) | 0.0112 (19) | 0.0005 (17) |
C106 | 0.020 (2) | 0.027 (2) | 0.037 (2) | 0.0003 (16) | 0.0053 (16) | −0.0042 (17) |
C107 | 0.0138 (18) | 0.0219 (19) | 0.0320 (19) | −0.0013 (15) | −0.0020 (15) | −0.0014 (15) |
C108 | 0.0171 (19) | 0.030 (2) | 0.032 (2) | −0.0010 (16) | −0.0037 (15) | 0.0015 (16) |
C109 | 0.038 (2) | 0.028 (2) | 0.031 (2) | −0.0028 (19) | 0.0018 (18) | 0.0024 (17) |
C110 | 0.023 (2) | 0.027 (2) | 0.0268 (19) | −0.0021 (16) | −0.0037 (15) | 0.0043 (15) |
C111 | 0.022 (2) | 0.033 (2) | 0.040 (2) | −0.0023 (18) | −0.0015 (17) | 0.0008 (18) |
C112 | 0.025 (2) | 0.037 (3) | 0.041 (2) | 0.0078 (19) | −0.0032 (18) | 0.0009 (19) |
C113 | 0.033 (2) | 0.027 (2) | 0.029 (2) | 0.0040 (18) | −0.0063 (17) | 0.0012 (16) |
C114 | 0.026 (2) | 0.030 (2) | 0.046 (2) | −0.0029 (18) | 0.0032 (18) | 0.0016 (18) |
C115 | 0.022 (2) | 0.025 (2) | 0.045 (2) | 0.0044 (17) | 0.0047 (17) | 0.0012 (17) |
C116 | 0.048 (3) | 0.028 (2) | 0.042 (2) | 0.007 (2) | −0.004 (2) | 0.0058 (18) |
C117 | 0.034 (3) | 0.029 (2) | 0.064 (3) | 0.007 (2) | −0.009 (2) | −0.008 (2) |
C118 | 0.067 (4) | 0.028 (3) | 0.088 (4) | −0.002 (3) | 0.003 (3) | −0.007 (3) |
C119 | 0.120 (5) | 0.041 (3) | 0.041 (3) | 0.002 (3) | −0.016 (3) | −0.003 (2) |
Cl2 | 0.0396 (6) | 0.0514 (7) | 0.0355 (6) | 0.0040 (5) | 0.0124 (5) | 0.0020 (5) |
O2 | 0.0136 (13) | 0.0449 (18) | 0.0371 (15) | 0.0014 (12) | −0.0030 (11) | −0.0086 (13) |
N2 | 0.0117 (15) | 0.0285 (17) | 0.0298 (16) | 0.0007 (13) | 0.0006 (12) | −0.0031 (13) |
C201 | 0.0169 (18) | 0.0186 (19) | 0.0298 (19) | 0.0047 (15) | −0.0039 (15) | −0.0002 (15) |
C202 | 0.0183 (19) | 0.023 (2) | 0.031 (2) | 0.0038 (15) | −0.0035 (15) | 0.0029 (15) |
C203 | 0.026 (2) | 0.028 (2) | 0.0277 (19) | 0.0104 (17) | 0.0011 (16) | 0.0052 (16) |
C204 | 0.039 (2) | 0.029 (2) | 0.028 (2) | 0.0111 (19) | −0.0076 (18) | −0.0055 (17) |
C205 | 0.033 (2) | 0.022 (2) | 0.042 (2) | −0.0004 (18) | −0.0144 (18) | −0.0021 (17) |
C206 | 0.0205 (19) | 0.022 (2) | 0.038 (2) | −0.0011 (16) | −0.0067 (16) | 0.0068 (16) |
C207 | 0.0136 (18) | 0.0196 (19) | 0.035 (2) | −0.0021 (15) | −0.0008 (15) | −0.0018 (15) |
C208 | 0.0161 (18) | 0.032 (2) | 0.033 (2) | −0.0044 (16) | 0.0044 (15) | −0.0061 (16) |
C209 | 0.037 (2) | 0.034 (2) | 0.035 (2) | −0.004 (2) | −0.0012 (19) | −0.0005 (18) |
C210 | 0.025 (2) | 0.031 (2) | 0.0269 (19) | −0.0023 (17) | 0.0021 (16) | −0.0056 (16) |
C211 | 0.024 (2) | 0.037 (3) | 0.056 (3) | 0.0004 (19) | −0.012 (2) | −0.006 (2) |
C212 | 0.038 (3) | 0.032 (3) | 0.057 (3) | 0.009 (2) | −0.020 (2) | −0.003 (2) |
C213 | 0.044 (3) | 0.032 (2) | 0.031 (2) | 0.000 (2) | −0.0034 (19) | −0.0034 (17) |
C214 | 0.032 (2) | 0.032 (2) | 0.048 (3) | −0.006 (2) | 0.0000 (19) | −0.0036 (19) |
C215 | 0.025 (2) | 0.030 (2) | 0.053 (3) | 0.0008 (18) | 0.0006 (19) | −0.0023 (19) |
C216 | 0.065 (3) | 0.035 (3) | 0.040 (2) | 0.004 (2) | −0.008 (2) | 0.002 (2) |
C217 | 0.039 (3) | 0.032 (2) | 0.050 (3) | 0.007 (2) | −0.010 (2) | 0.000 (2) |
C218 | 0.055 (3) | 0.027 (3) | 0.082 (4) | 0.002 (2) | −0.004 (3) | −0.007 (2) |
C219 | 0.093 (5) | 0.042 (3) | 0.067 (4) | 0.006 (3) | 0.025 (3) | 0.002 (3) |
Cl1—C103 | 1.735 (4) | Cl2—C203 | 1.738 (4) |
O1—C107 | 1.229 (4) | O2—C207 | 1.232 (4) |
N1—C107 | 1.355 (5) | N2—C207 | 1.344 (5) |
N1—C101 | 1.402 (5) | N2—C201 | 1.419 (5) |
N1—H1A | 0.8800 | N2—H2A | 0.8800 |
C101—C106 | 1.386 (5) | C201—C202 | 1.381 (5) |
C101—C102 | 1.393 (5) | C201—C206 | 1.387 (5) |
C102—C103 | 1.377 (5) | C202—C203 | 1.367 (5) |
C102—H10A | 0.9500 | C202—H20A | 0.9500 |
C103—C104 | 1.376 (6) | C203—C204 | 1.377 (6) |
C104—C105 | 1.390 (6) | C204—C205 | 1.375 (6) |
C104—H10B | 0.9500 | C204—H20B | 0.9500 |
C105—C106 | 1.376 (6) | C205—C206 | 1.389 (6) |
C105—H10C | 0.9500 | C205—H20C | 0.9500 |
C106—H10H | 0.9500 | C206—H20H | 0.9500 |
C107—C108 | 1.506 (5) | C207—C208 | 1.520 (5) |
C108—C110 | 1.517 (5) | C208—C210 | 1.518 (5) |
C108—C109 | 1.529 (5) | C208—C209 | 1.524 (6) |
C108—H10G | 1.0000 | C208—H20G | 1.0000 |
C109—H10D | 0.9800 | C209—H20D | 0.9800 |
C109—H10E | 0.9800 | C209—H20E | 0.9800 |
C109—H10F | 0.9800 | C209—H20F | 0.9800 |
C110—C111 | 1.380 (5) | C210—C211 | 1.385 (6) |
C110—C115 | 1.387 (5) | C210—C215 | 1.388 (6) |
C111—C112 | 1.376 (6) | C211—C212 | 1.381 (6) |
C111—H11A | 0.9500 | C211—H21A | 0.9500 |
C112—C113 | 1.389 (6) | C212—C213 | 1.391 (6) |
C112—H11B | 0.9500 | C212—H21B | 0.9500 |
C113—C114 | 1.401 (6) | C213—C214 | 1.375 (6) |
C113—C116 | 1.494 (6) | C213—C216 | 1.508 (6) |
C114—C115 | 1.367 (6) | C214—C215 | 1.376 (6) |
C114—H11C | 0.9500 | C214—H21C | 0.9500 |
C115—H11D | 0.9500 | C215—H21D | 0.9500 |
C116—C117 | 1.514 (6) | C216—C217 | 1.520 (6) |
C116—H11E | 0.9900 | C216—H21E | 0.9900 |
C116—H11F | 0.9900 | C216—H21F | 0.9900 |
C117—C119 | 1.498 (7) | C217—C218 | 1.513 (6) |
C117—C118 | 1.533 (6) | C217—C219 | 1.519 (7) |
C117—H11G | 1.0000 | C217—H21G | 1.0000 |
C118—H11H | 0.9800 | C218—H21H | 0.9800 |
C118—H11I | 0.9800 | C218—H21I | 0.9800 |
C118—H11J | 0.9800 | C218—H21J | 0.9800 |
C119—H11K | 0.9800 | C219—H21K | 0.9800 |
C119—H11L | 0.9800 | C219—H21L | 0.9800 |
C119—H11M | 0.9800 | C219—H21M | 0.9800 |
C107—N1—C101 | 126.4 (3) | C207—N2—C201 | 125.1 (3) |
C107—N1—H1A | 116.8 | C207—N2—H2A | 117.5 |
C101—N1—H1A | 116.8 | C201—N2—H2A | 117.5 |
C106—C101—C102 | 119.6 (3) | C202—C201—C206 | 120.4 (3) |
C106—C101—N1 | 118.5 (3) | C202—C201—N2 | 121.1 (3) |
C102—C101—N1 | 121.8 (3) | C206—C201—N2 | 118.4 (3) |
C103—C102—C101 | 118.7 (4) | C203—C202—C201 | 118.6 (4) |
C103—C102—H10A | 120.7 | C203—C202—H20A | 120.7 |
C101—C102—H10A | 120.7 | C201—C202—H20A | 120.7 |
C104—C103—C102 | 122.4 (4) | C202—C203—C204 | 122.6 (4) |
C104—C103—Cl1 | 119.2 (3) | C202—C203—Cl2 | 118.4 (3) |
C102—C103—Cl1 | 118.4 (3) | C204—C203—Cl2 | 119.0 (3) |
C103—C104—C105 | 118.3 (4) | C205—C204—C203 | 118.3 (4) |
C103—C104—H10B | 120.8 | C205—C204—H20B | 120.8 |
C105—C104—H10B | 120.8 | C203—C204—H20B | 120.8 |
C106—C105—C104 | 120.3 (4) | C204—C205—C206 | 120.7 (4) |
C106—C105—H10C | 119.8 | C204—C205—H20C | 119.7 |
C104—C105—H10C | 119.8 | C206—C205—H20C | 119.7 |
C105—C106—C101 | 120.6 (4) | C201—C206—C205 | 119.4 (4) |
C105—C106—H10H | 119.7 | C201—C206—H20H | 120.3 |
C101—C106—H10H | 119.7 | C205—C206—H20H | 120.3 |
O1—C107—N1 | 121.7 (3) | O2—C207—N2 | 122.7 (3) |
O1—C107—C108 | 122.6 (3) | O2—C207—C208 | 121.8 (3) |
N1—C107—C108 | 115.7 (3) | N2—C207—C208 | 115.5 (3) |
C107—C108—C110 | 109.6 (3) | C210—C208—C207 | 108.0 (3) |
C107—C108—C109 | 110.5 (3) | C210—C208—C209 | 113.3 (3) |
C110—C108—C109 | 113.0 (3) | C207—C208—C209 | 110.9 (3) |
C107—C108—H10G | 107.8 | C210—C208—H20G | 108.2 |
C110—C108—H10G | 107.8 | C207—C208—H20G | 108.1 |
C109—C108—H10G | 107.8 | C209—C208—H20G | 108.2 |
C108—C109—H10D | 109.5 | C208—C209—H20D | 109.5 |
C108—C109—H10E | 109.5 | C208—C209—H20E | 109.5 |
H10D—C109—H10E | 109.5 | H20D—C209—H20E | 109.5 |
C108—C109—H10F | 109.5 | C208—C209—H20F | 109.5 |
H10D—C109—H10F | 109.5 | H20D—C209—H20F | 109.5 |
H10E—C109—H10F | 109.5 | H20E—C209—H20F | 109.5 |
C111—C110—C115 | 117.8 (4) | C211—C210—C215 | 117.2 (4) |
C111—C110—C108 | 121.0 (3) | C211—C210—C208 | 120.8 (4) |
C115—C110—C108 | 121.2 (3) | C215—C210—C208 | 121.9 (4) |
C112—C111—C110 | 120.8 (4) | C212—C211—C210 | 121.5 (4) |
C112—C111—H11A | 119.6 | C212—C211—H21A | 119.2 |
C110—C111—H11A | 119.6 | C210—C211—H21A | 119.3 |
C111—C112—C113 | 122.1 (4) | C211—C212—C213 | 120.8 (4) |
C111—C112—H11B | 118.9 | C211—C212—H21B | 119.6 |
C113—C112—H11B | 118.9 | C213—C212—H21B | 119.6 |
C112—C113—C114 | 116.3 (4) | C214—C213—C212 | 117.7 (4) |
C112—C113—C116 | 122.1 (4) | C214—C213—C216 | 120.1 (4) |
C114—C113—C116 | 121.7 (4) | C212—C213—C216 | 122.2 (4) |
C115—C114—C113 | 121.6 (4) | C213—C214—C215 | 121.5 (4) |
C115—C114—H11C | 119.2 | C213—C214—H21C | 119.2 |
C113—C114—H11C | 119.2 | C215—C214—H21C | 119.2 |
C114—C115—C110 | 121.3 (4) | C214—C215—C210 | 121.3 (4) |
C114—C115—H11D | 119.3 | C214—C215—H21D | 119.4 |
C110—C115—H11D | 119.3 | C210—C215—H21D | 119.4 |
C113—C116—C117 | 114.7 (4) | C213—C216—C217 | 114.9 (4) |
C113—C116—H11E | 108.6 | C213—C216—H21E | 108.5 |
C117—C116—H11E | 108.6 | C217—C216—H21E | 108.5 |
C113—C116—H11F | 108.6 | C213—C216—H21F | 108.5 |
C117—C116—H11F | 108.6 | C217—C216—H21F | 108.5 |
H11E—C116—H11F | 107.6 | H21E—C216—H21F | 107.5 |
C119—C117—C116 | 112.4 (4) | C218—C217—C219 | 110.5 (4) |
C119—C117—C118 | 110.4 (4) | C218—C217—C216 | 111.0 (4) |
C116—C117—C118 | 111.1 (4) | C219—C217—C216 | 111.3 (4) |
C119—C117—H11G | 107.6 | C218—C217—H21G | 107.9 |
C116—C117—H11G | 107.6 | C219—C217—H21G | 107.9 |
C118—C117—H11G | 107.6 | C216—C217—H21G | 107.9 |
C117—C118—H11H | 109.5 | C217—C218—H21H | 109.5 |
C117—C118—H11I | 109.5 | C217—C218—H21I | 109.5 |
H11H—C118—H11I | 109.5 | H21H—C218—H21I | 109.5 |
C117—C118—H11J | 109.5 | C217—C218—H21J | 109.5 |
H11H—C118—H11J | 109.5 | H21H—C218—H21J | 109.5 |
H11I—C118—H11J | 109.5 | H21I—C218—H21J | 109.5 |
C117—C119—H11K | 109.5 | C217—C219—H21K | 109.5 |
C117—C119—H11L | 109.5 | C217—C219—H21L | 109.5 |
H11K—C119—H11L | 109.5 | H21K—C219—H21L | 109.5 |
C117—C119—H11M | 109.5 | C217—C219—H21M | 109.5 |
H11K—C119—H11M | 109.5 | H21K—C219—H21M | 109.5 |
H11L—C119—H11M | 109.5 | H21L—C219—H21M | 109.5 |
C107—N1—C101—C106 | 147.6 (4) | C207—N2—C201—C202 | 39.4 (5) |
C107—N1—C101—C102 | −35.0 (5) | C207—N2—C201—C206 | −143.2 (4) |
C106—C101—C102—C103 | −0.2 (5) | C206—C201—C202—C203 | 0.1 (5) |
N1—C101—C102—C103 | −177.6 (3) | N2—C201—C202—C203 | 177.4 (3) |
C101—C102—C103—C104 | −0.8 (6) | C201—C202—C203—C204 | 1.1 (6) |
C101—C102—C103—Cl1 | 179.0 (3) | C201—C202—C203—Cl2 | −178.5 (3) |
C102—C103—C104—C105 | 1.7 (6) | C202—C203—C204—C205 | −1.9 (6) |
Cl1—C103—C104—C105 | −178.0 (3) | Cl2—C203—C204—C205 | 177.7 (3) |
C103—C104—C105—C106 | −1.6 (6) | C203—C204—C205—C206 | 1.5 (6) |
C104—C105—C106—C101 | 0.7 (6) | C202—C201—C206—C205 | −0.4 (5) |
C102—C101—C106—C105 | 0.3 (5) | N2—C201—C206—C205 | −177.8 (3) |
N1—C101—C106—C105 | 177.8 (3) | C204—C205—C206—C201 | −0.4 (6) |
C101—N1—C107—O1 | 1.4 (6) | C201—N2—C207—O2 | −1.0 (6) |
C101—N1—C107—C108 | −178.5 (3) | C201—N2—C207—C208 | −179.2 (3) |
O1—C107—C108—C110 | 82.6 (4) | O2—C207—C208—C210 | −80.6 (4) |
N1—C107—C108—C110 | −97.5 (4) | N2—C207—C208—C210 | 97.5 (4) |
O1—C107—C108—C109 | −42.6 (5) | O2—C207—C208—C209 | 44.1 (5) |
N1—C107—C108—C109 | 137.3 (3) | N2—C207—C208—C209 | −137.8 (3) |
C107—C108—C110—C111 | 104.3 (4) | C207—C208—C210—C211 | −103.7 (4) |
C109—C108—C110—C111 | −131.9 (4) | C209—C208—C210—C211 | 133.0 (4) |
C107—C108—C110—C115 | −74.8 (4) | C207—C208—C210—C215 | 75.3 (5) |
C109—C108—C110—C115 | 48.9 (5) | C209—C208—C210—C215 | −48.0 (5) |
C115—C110—C111—C112 | −1.4 (6) | C215—C210—C211—C212 | −0.5 (6) |
C108—C110—C111—C112 | 179.4 (4) | C208—C210—C211—C212 | 178.6 (4) |
C110—C111—C112—C113 | −0.4 (6) | C210—C211—C212—C213 | −0.1 (7) |
C111—C112—C113—C114 | 1.5 (6) | C211—C212—C213—C214 | 0.9 (7) |
C111—C112—C113—C116 | −179.2 (4) | C211—C212—C213—C216 | −179.4 (4) |
C112—C113—C114—C115 | −0.9 (6) | C212—C213—C214—C215 | −1.2 (7) |
C116—C113—C114—C115 | 179.8 (4) | C216—C213—C214—C215 | 179.0 (4) |
C113—C114—C115—C110 | −0.9 (6) | C213—C214—C215—C210 | 0.7 (7) |
C111—C110—C115—C114 | 2.0 (6) | C211—C210—C215—C214 | 0.1 (6) |
C108—C110—C115—C114 | −178.8 (4) | C208—C210—C215—C214 | −178.9 (4) |
C112—C113—C116—C117 | −114.6 (5) | C214—C213—C216—C217 | 71.8 (6) |
C114—C113—C116—C117 | 64.7 (5) | C212—C213—C216—C217 | −107.9 (5) |
C113—C116—C117—C119 | 60.3 (5) | C213—C216—C217—C218 | −168.0 (4) |
C113—C116—C117—C118 | −175.5 (4) | C213—C216—C217—C219 | 68.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 1.95 | 2.821 (4) | 169 |
N2—H2A···O1 | 0.88 | 1.93 | 2.800 (4) | 168 |
Symmetry code: (i) x+1, y, z. |