Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021817/cf2036sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021817/cf2036Isup2.hkl |
CCDC reference: 613630
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
C36H36N3O3+·Cl−·2CH4O | F(000) = 1400 |
Mr = 658.21 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/c | Melting point: 479 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.014 (2) Å | Cell parameters from 2624 reflections |
b = 17.131 (4) Å | θ = 2.2–22.6° |
c = 19.055 (4) Å | µ = 0.15 mm−1 |
β = 100.498 (7)° | T = 173 K |
V = 3535.3 (12) Å3 | Block, colourless |
Z = 4 | 0.45 × 0.32 × 0.27 mm |
Bruker SMART 1000 CCD diffractometer | 3117 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.095 |
Graphite monochromator | θmax = 23.3°, θmin = 1.6° |
thin–slice ω scans | h = −12→12 |
26495 measured reflections | k = −19→18 |
4996 independent reflections | l = −21→21 |
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)] = 0.067 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.231 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1544P)2] where P = (Fo2 + 2Fc2)/3 |
4996 reflections | (Δ/σ)max < 0.001 |
434 parameters | Δρmax = 0.52 e Å−3 |
2 restraints | Δρmin = −0.56 e Å−3 |
Experimental. Additional analytical data for (I) 1H NMR (CDCl3, 600 MHz, p.p.m.): 1.82 (d, 1H, J=13.2 Hz), 2.05 (m, 2H), 2.15 (qd, 1H, J1=3 Hz, J2=12.6 Hz), 2.40 (s, 2H), 2.99 (m, 2H), 3.17 (s, 4H), 3.32 (dd, 1H, J1=5.4 Hz, J2=14.4 Hz), 3.41 (m, 3H), 3.55 (br.m, 2H), 4.83 (tt, 1H, J1=3 Hz, J2=12 Hz), 4.97 (dd, 1H, J1=5.4 Hz, J2=10.2 Hz), 6.89 (d, 2H, J=7.2 Hz), 6.96 (d, 1H, J=7.8 Hz), 7.08 (m, 5H), 7.21 (m, 3H), 7.28 (m, 3H), 7.42 (t, 1H, J=7.2 Hz), 7.64 (br.s, 4H).13 C NMR (CDCl3, 600 MHz, p.p.m.): 27.2, 27.6, 30.2, 34.9, 50.3, 51.4, 51.9, 52.1, 53.6, 58.1, 123.2, 126.6, 127.2, 128.3, 128.7, 128.8, 128.9, 129.2, 129.3, 129.8, 130.2, 131.3, 134.1, 136.1, 136.3, 136.8, 166.9, 168.4. |
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. Despite containing a stereogenic centre this compound was crystallized as a racemic mixture and did not resolve into two enantiomers upon crystallization. The space group is P21/c. The c-glide plane was clearly identified by systematic absence data and so the correctness of the space group was verified by refining models in space groups with m point group symmetry. In all cases the refinement resulted in many highly correlated parameters and we are confident that the centrosymmetric P21/c is the correct space group. |
x | y | z | Uiso*/Ueq | ||
Cl | 0.99764 (12) | 0.33004 (6) | 0.46571 (8) | 0.0719 (5) | |
O1 | 0.6649 (3) | 0.22725 (15) | 0.78818 (14) | 0.0462 (8) | |
O2 | 0.4742 (3) | 0.46303 (15) | 0.73538 (13) | 0.0434 (7) | |
O3 | 0.4286 (3) | 0.38800 (15) | 0.57316 (14) | 0.0450 (8) | |
O4 | 0.4271 (4) | 0.1701 (3) | 0.5509 (2) | 0.0944 (13) | |
H4O | 0.356 (3) | 0.164 (4) | 0.528 (3) | 0.113* | |
O5 | 0.1745 (3) | 0.19250 (19) | 0.51494 (17) | 0.0630 (9) | |
H5O | 0.151 (5) | 0.2351 (15) | 0.499 (3) | 0.076* | |
N1 | 0.5575 (3) | 0.33861 (16) | 0.74457 (15) | 0.0314 (8) | |
N2 | 0.6336 (3) | 0.36983 (16) | 0.60648 (14) | 0.0337 (8) | |
N3 | 0.7897 (3) | 0.44783 (17) | 0.42702 (15) | 0.0350 (8) | |
H3N | 0.851 (4) | 0.406 (2) | 0.4350 (19) | 0.042* | |
C1 | 0.6398 (4) | 0.2954 (2) | 0.7950 (2) | 0.0376 (10) | |
C2 | 0.6833 (4) | 0.3504 (2) | 0.85489 (19) | 0.0365 (10) | |
C3 | 0.7695 (4) | 0.3390 (3) | 0.9172 (2) | 0.0497 (12) | |
H3 | 0.8129 | 0.2912 | 0.9272 | 0.060* | |
C4 | 0.7879 (5) | 0.4024 (3) | 0.9641 (2) | 0.0576 (13) | |
H4 | 0.8454 | 0.3974 | 1.0076 | 0.069* | |
C5 | 0.7251 (5) | 0.4721 (3) | 0.9494 (2) | 0.0553 (12) | |
H5 | 0.7403 | 0.5138 | 0.9827 | 0.066* | |
C6 | 0.6402 (4) | 0.4822 (2) | 0.8866 (2) | 0.0483 (11) | |
H6 | 0.5965 | 0.5299 | 0.8763 | 0.058* | |
C7 | 0.6222 (4) | 0.4201 (2) | 0.84000 (19) | 0.0367 (10) | |
C8 | 0.5402 (4) | 0.4139 (2) | 0.76863 (19) | 0.0358 (10) | |
C9 | 0.4932 (4) | 0.3066 (2) | 0.67645 (19) | 0.0377 (10) | |
H9 | 0.5309 | 0.2546 | 0.6701 | 0.045* | |
C10 | 0.3572 (4) | 0.2932 (2) | 0.6757 (2) | 0.0451 (11) | |
H10A | 0.3205 | 0.2669 | 0.6306 | 0.054* | |
H10B | 0.3159 | 0.3445 | 0.6767 | 0.054* | |
C11 | 0.3318 (4) | 0.2443 (2) | 0.7381 (2) | 0.0393 (10) | |
C12 | 0.3735 (4) | 0.1678 (2) | 0.7488 (2) | 0.0519 (12) | |
H12 | 0.4195 | 0.1451 | 0.7164 | 0.062* | |
C13 | 0.3490 (4) | 0.1238 (3) | 0.8063 (3) | 0.0569 (13) | |
H13 | 0.3778 | 0.0716 | 0.8130 | 0.068* | |
C14 | 0.2826 (5) | 0.1572 (3) | 0.8531 (3) | 0.0613 (14) | |
H14 | 0.2659 | 0.1281 | 0.8927 | 0.074* | |
C15 | 0.2407 (5) | 0.2321 (3) | 0.8426 (3) | 0.0662 (15) | |
H15 | 0.1937 | 0.2548 | 0.8745 | 0.079* | |
C16 | 0.2665 (5) | 0.2748 (2) | 0.7861 (2) | 0.0520 (12) | |
H16 | 0.2380 | 0.3272 | 0.7802 | 0.062* | |
C17 | 0.5144 (4) | 0.3585 (2) | 0.61410 (19) | 0.0342 (9) | |
C18 | 0.7350 (4) | 0.3229 (2) | 0.64281 (19) | 0.0334 (9) | |
C19 | 0.7504 (4) | 0.2458 (2) | 0.62211 (19) | 0.0377 (10) | |
H19 | 0.6931 | 0.2235 | 0.5841 | 0.045* | |
C20 | 0.8471 (4) | 0.2027 (2) | 0.6563 (2) | 0.0419 (11) | |
H20 | 0.8550 | 0.1497 | 0.6430 | 0.050* | |
C21 | 0.9333 (4) | 0.2347 (2) | 0.7096 (2) | 0.0452 (11) | |
H21 | 1.0017 | 0.2045 | 0.7321 | 0.054* | |
C22 | 0.9202 (4) | 0.3116 (2) | 0.7305 (2) | 0.0433 (11) | |
H22 | 0.9793 | 0.3341 | 0.7675 | 0.052* | |
C23 | 0.8206 (4) | 0.3549 (2) | 0.69712 (19) | 0.0370 (10) | |
H23 | 0.8109 | 0.4072 | 0.7117 | 0.044* | |
C24 | 0.6568 (4) | 0.4168 (2) | 0.54395 (17) | 0.0342 (10) | |
H24 | 0.5945 | 0.4599 | 0.5361 | 0.041* | |
C25 | 0.7831 (4) | 0.4536 (2) | 0.55617 (19) | 0.0350 (10) | |
H25A | 0.8467 | 0.4123 | 0.5666 | 0.042* | |
H25B | 0.7921 | 0.4886 | 0.5981 | 0.042* | |
C26 | 0.8038 (4) | 0.5001 (2) | 0.49120 (18) | 0.0344 (10) | |
H26A | 0.7432 | 0.5432 | 0.4821 | 0.041* | |
H26B | 0.8877 | 0.5231 | 0.5004 | 0.041* | |
C27 | 0.6620 (4) | 0.4137 (2) | 0.41223 (19) | 0.0371 (10) | |
H27A | 0.6531 | 0.3793 | 0.3699 | 0.045* | |
H27B | 0.6004 | 0.4562 | 0.4017 | 0.045* | |
C28 | 0.6376 (4) | 0.3668 (2) | 0.47646 (18) | 0.0376 (10) | |
H28A | 0.5519 | 0.3469 | 0.4667 | 0.045* | |
H28B | 0.6941 | 0.3214 | 0.4840 | 0.045* | |
C29 | 0.8217 (4) | 0.4900 (2) | 0.36378 (19) | 0.0384 (10) | |
H29A | 0.9007 | 0.5183 | 0.3785 | 0.046* | |
H29B | 0.7568 | 0.5290 | 0.3465 | 0.046* | |
C30 | 0.8336 (6) | 0.4345 (3) | 0.3040 (3) | 0.081 (2) | |
H30A | 0.8916 | 0.3922 | 0.3229 | 0.097* | |
H30B | 0.7521 | 0.4104 | 0.2861 | 0.097* | |
C31 | 0.8783 (5) | 0.4732 (2) | 0.2432 (2) | 0.0452 (11) | |
C32 | 0.7991 (4) | 0.5133 (2) | 0.1908 (2) | 0.0517 (12) | |
H32 | 0.7145 | 0.5172 | 0.1946 | 0.062* | |
C33 | 0.8373 (7) | 0.5476 (3) | 0.1341 (2) | 0.0657 (15) | |
H33 | 0.7804 | 0.5758 | 0.0999 | 0.079* | |
C34 | 0.9543 (8) | 0.5413 (3) | 0.1270 (3) | 0.0780 (19) | |
H34 | 0.9804 | 0.5643 | 0.0869 | 0.094* | |
C35 | 1.0382 (5) | 0.5020 (3) | 0.1764 (3) | 0.0685 (16) | |
H35 | 1.1218 | 0.4975 | 0.1706 | 0.082* | |
C36 | 0.9996 (5) | 0.4685 (2) | 0.2357 (3) | 0.0559 (14) | |
H36 | 1.0577 | 0.4425 | 0.2710 | 0.067* | |
C37 | 0.4719 (6) | 0.1469 (4) | 0.4906 (4) | 0.114 (3) | |
H37A | 0.5168 | 0.1903 | 0.4736 | 0.171* | |
H37B | 0.4027 | 0.1317 | 0.4531 | 0.171* | |
H37C | 0.5278 | 0.1024 | 0.5025 | 0.171* | |
C38 | 0.1162 (5) | 0.1637 (3) | 0.5696 (3) | 0.0685 (14) | |
H38A | 0.0573 | 0.1228 | 0.5504 | 0.103* | |
H38B | 0.0723 | 0.2064 | 0.5885 | 0.103* | |
H38C | 0.1785 | 0.1420 | 0.6080 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0544 (9) | 0.0395 (7) | 0.1177 (12) | 0.0071 (5) | 0.0049 (8) | −0.0024 (6) |
O1 | 0.054 (2) | 0.0361 (16) | 0.0494 (17) | 0.0103 (13) | 0.0103 (15) | 0.0088 (13) |
O2 | 0.0472 (18) | 0.0371 (15) | 0.0435 (16) | 0.0084 (13) | 0.0021 (14) | 0.0049 (13) |
O3 | 0.0438 (19) | 0.0494 (16) | 0.0392 (16) | 0.0073 (14) | 0.0005 (14) | 0.0114 (13) |
O4 | 0.082 (3) | 0.117 (3) | 0.084 (3) | 0.023 (3) | 0.016 (2) | −0.019 (2) |
O5 | 0.068 (2) | 0.067 (2) | 0.057 (2) | 0.0201 (19) | 0.0184 (18) | 0.0108 (17) |
N1 | 0.0322 (19) | 0.0327 (17) | 0.0287 (16) | 0.0021 (14) | 0.0032 (14) | 0.0039 (13) |
N2 | 0.044 (2) | 0.0316 (17) | 0.0247 (17) | 0.0000 (15) | 0.0040 (15) | 0.0031 (13) |
N3 | 0.044 (2) | 0.0268 (16) | 0.0336 (18) | −0.0004 (15) | 0.0048 (15) | 0.0002 (14) |
C1 | 0.037 (3) | 0.042 (2) | 0.035 (2) | 0.0010 (19) | 0.0089 (19) | 0.0110 (18) |
C2 | 0.034 (2) | 0.046 (2) | 0.031 (2) | −0.0071 (19) | 0.0067 (18) | 0.0089 (18) |
C3 | 0.054 (3) | 0.057 (3) | 0.039 (2) | −0.003 (2) | 0.008 (2) | 0.015 (2) |
C4 | 0.058 (3) | 0.083 (3) | 0.028 (2) | −0.013 (3) | −0.004 (2) | 0.002 (2) |
C5 | 0.061 (3) | 0.063 (3) | 0.040 (3) | −0.006 (3) | 0.006 (2) | −0.009 (2) |
C6 | 0.059 (3) | 0.046 (2) | 0.040 (2) | −0.006 (2) | 0.010 (2) | −0.004 (2) |
C7 | 0.039 (2) | 0.040 (2) | 0.031 (2) | −0.0053 (19) | 0.0077 (18) | 0.0024 (18) |
C8 | 0.039 (3) | 0.034 (2) | 0.035 (2) | 0.0003 (19) | 0.0091 (19) | 0.0063 (18) |
C9 | 0.040 (3) | 0.040 (2) | 0.031 (2) | −0.0025 (19) | 0.0025 (19) | −0.0004 (17) |
C10 | 0.050 (3) | 0.042 (2) | 0.041 (2) | −0.006 (2) | 0.003 (2) | −0.0010 (19) |
C11 | 0.045 (3) | 0.034 (2) | 0.037 (2) | −0.0091 (19) | 0.001 (2) | −0.0023 (18) |
C12 | 0.056 (3) | 0.049 (3) | 0.052 (3) | −0.002 (2) | 0.015 (2) | −0.008 (2) |
C13 | 0.057 (3) | 0.039 (2) | 0.071 (3) | −0.006 (2) | 0.002 (3) | 0.010 (2) |
C14 | 0.077 (4) | 0.057 (3) | 0.051 (3) | −0.015 (3) | 0.016 (3) | 0.009 (2) |
C15 | 0.087 (4) | 0.055 (3) | 0.065 (3) | −0.008 (3) | 0.036 (3) | −0.005 (2) |
C16 | 0.064 (3) | 0.037 (2) | 0.057 (3) | 0.001 (2) | 0.018 (3) | 0.000 (2) |
C17 | 0.038 (3) | 0.031 (2) | 0.032 (2) | −0.0026 (19) | 0.003 (2) | −0.0014 (17) |
C18 | 0.037 (2) | 0.032 (2) | 0.030 (2) | 0.0023 (17) | 0.0042 (18) | 0.0025 (16) |
C19 | 0.050 (3) | 0.035 (2) | 0.027 (2) | −0.0006 (19) | 0.0048 (19) | 0.0019 (17) |
C20 | 0.051 (3) | 0.037 (2) | 0.037 (2) | 0.006 (2) | 0.007 (2) | 0.0000 (18) |
C21 | 0.040 (3) | 0.047 (2) | 0.048 (3) | 0.011 (2) | 0.007 (2) | 0.007 (2) |
C22 | 0.041 (3) | 0.049 (2) | 0.037 (2) | −0.004 (2) | −0.002 (2) | 0.0010 (19) |
C23 | 0.040 (2) | 0.035 (2) | 0.034 (2) | 0.0001 (19) | 0.0020 (19) | −0.0012 (17) |
C24 | 0.047 (3) | 0.0292 (19) | 0.025 (2) | −0.0008 (18) | 0.0044 (18) | 0.0014 (15) |
C25 | 0.042 (3) | 0.0302 (19) | 0.031 (2) | 0.0020 (17) | 0.0012 (18) | −0.0008 (16) |
C26 | 0.037 (2) | 0.0285 (19) | 0.036 (2) | −0.0056 (17) | 0.0009 (18) | −0.0028 (17) |
C27 | 0.050 (3) | 0.032 (2) | 0.029 (2) | −0.0053 (19) | 0.0040 (19) | −0.0035 (16) |
C28 | 0.048 (3) | 0.032 (2) | 0.031 (2) | −0.0080 (18) | 0.0033 (19) | −0.0011 (16) |
C29 | 0.054 (3) | 0.0266 (19) | 0.035 (2) | −0.0041 (18) | 0.0097 (19) | 0.0055 (17) |
C30 | 0.162 (6) | 0.037 (2) | 0.061 (3) | −0.021 (3) | 0.065 (4) | −0.006 (2) |
C31 | 0.066 (3) | 0.029 (2) | 0.043 (3) | −0.003 (2) | 0.015 (2) | −0.0077 (18) |
C32 | 0.049 (3) | 0.047 (2) | 0.059 (3) | 0.001 (2) | 0.010 (2) | −0.017 (2) |
C33 | 0.099 (5) | 0.059 (3) | 0.037 (3) | 0.006 (3) | 0.005 (3) | −0.003 (2) |
C34 | 0.134 (6) | 0.060 (3) | 0.047 (3) | −0.026 (4) | 0.034 (4) | −0.009 (3) |
C35 | 0.062 (4) | 0.070 (3) | 0.085 (4) | −0.027 (3) | 0.043 (3) | −0.039 (3) |
C36 | 0.064 (4) | 0.042 (2) | 0.055 (3) | 0.000 (2) | −0.006 (3) | −0.015 (2) |
C37 | 0.075 (5) | 0.145 (6) | 0.130 (6) | −0.018 (4) | 0.043 (4) | −0.077 (5) |
C38 | 0.061 (4) | 0.076 (3) | 0.069 (3) | −0.006 (3) | 0.012 (3) | 0.012 (3) |
O1—C1 | 1.212 (4) | C18—C23 | 1.380 (5) |
O2—C8 | 1.212 (4) | C19—H19 | 0.950 |
O3—C17 | 1.220 (4) | C19—C20 | 1.361 (6) |
O4—H4O | 0.83 (19) | C20—H20 | 0.950 |
O4—C37 | 1.390 (7) | C20—C21 | 1.373 (6) |
O5—H5O | 0.82 (19) | C21—H21 | 0.950 |
O5—C38 | 1.409 (6) | C21—C22 | 1.390 (5) |
N1—C1 | 1.406 (5) | C22—H22 | 0.950 |
N1—C8 | 1.394 (5) | C22—C23 | 1.380 (5) |
N1—C9 | 1.467 (5) | C23—H23 | 0.950 |
N2—C17 | 1.360 (5) | C24—H24 | 1.000 |
N2—C18 | 1.447 (5) | C24—C25 | 1.507 (5) |
N2—C24 | 1.498 (4) | C24—C28 | 1.527 (5) |
N3—H3N | 0.98 (4) | C25—H25A | 0.990 |
N3—C26 | 1.501 (4) | C25—H25B | 0.990 |
N3—C27 | 1.502 (5) | C25—C26 | 1.524 (5) |
N3—C29 | 1.502 (5) | C26—H26A | 0.990 |
C1—C2 | 1.490 (5) | C26—H26B | 0.990 |
C2—C3 | 1.392 (6) | C27—H27A | 0.990 |
C2—C7 | 1.375 (5) | C27—H27B | 0.990 |
C3—H3 | 0.950 | C27—C28 | 1.528 (5) |
C3—C4 | 1.399 (6) | C28—H28A | 0.990 |
C4—H4 | 0.950 | C28—H28B | 0.990 |
C4—C5 | 1.384 (6) | C29—H29A | 0.990 |
C5—H5 | 0.950 | C29—H29B | 0.990 |
C5—C6 | 1.388 (6) | C29—C30 | 1.509 (5) |
C6—H6 | 0.950 | C30—H30A | 0.990 |
C6—C7 | 1.377 (5) | C30—H30B | 0.990 |
C7—C8 | 1.493 (5) | C30—C31 | 1.494 (6) |
C9—H9 | 1.000 | C31—C32 | 1.383 (6) |
C9—C10 | 1.513 (6) | C31—C36 | 1.371 (6) |
C9—C17 | 1.535 (5) | C32—H32 | 0.950 |
C10—H10A | 0.990 | C32—C33 | 1.362 (7) |
C10—H10B | 0.990 | C33—H33 | 0.950 |
C10—C11 | 1.521 (6) | C33—C34 | 1.324 (8) |
C11—C12 | 1.391 (5) | C34—H34 | 0.950 |
C11—C16 | 1.367 (6) | C34—C35 | 1.370 (8) |
C12—H12 | 0.950 | C35—H35 | 0.950 |
C12—C13 | 1.396 (6) | C35—C36 | 1.401 (7) |
C13—H13 | 0.950 | C36—H36 | 0.950 |
C13—C14 | 1.377 (7) | C37—H37A | 0.980 |
C14—H14 | 0.950 | C37—H37B | 0.980 |
C14—C15 | 1.367 (7) | C37—H37C | 0.980 |
C15—H15 | 0.950 | C38—H38A | 0.980 |
C15—C16 | 1.372 (6) | C38—H38B | 0.980 |
C16—H16 | 0.950 | C38—H38C | 0.980 |
C18—C19 | 1.397 (5) | ||
H4O—O4—C37 | 88 (5) | C20—C21—C22 | 119.8 (4) |
H5O—O5—C38 | 116 (4) | H21—C21—C22 | 120.1 |
C1—N1—C8 | 111.8 (3) | C21—C22—H22 | 120.2 |
C1—N1—C9 | 123.7 (3) | C21—C22—C23 | 119.5 (4) |
C8—N1—C9 | 124.3 (3) | H22—C22—C23 | 120.2 |
C17—N2—C18 | 123.1 (3) | C18—C23—C22 | 120.6 (4) |
C17—N2—C24 | 118.0 (3) | C18—C23—H23 | 119.7 |
C18—N2—C24 | 116.8 (3) | C22—C23—H23 | 119.7 |
H3N—N3—C26 | 110 (2) | N2—C24—H24 | 107.6 |
H3N—N3—C27 | 110 (2) | N2—C24—C25 | 112.9 (3) |
H3N—N3—C29 | 103 (2) | N2—C24—C28 | 110.6 (3) |
C26—N3—C27 | 109.9 (3) | H24—C24—C25 | 107.6 |
C26—N3—C29 | 111.2 (3) | H24—C24—C28 | 107.6 |
C27—N3—C29 | 112.7 (3) | C25—C24—C28 | 110.3 (3) |
O1—C1—N1 | 124.4 (4) | C24—C25—H25A | 109.4 |
O1—C1—C2 | 130.1 (4) | C24—C25—H25B | 109.4 |
N1—C1—C2 | 105.5 (3) | C24—C25—C26 | 111.3 (3) |
C1—C2—C3 | 129.7 (4) | H25A—C25—H25B | 108.0 |
C1—C2—C7 | 108.3 (3) | H25A—C25—C26 | 109.4 |
C3—C2—C7 | 122.0 (4) | H25B—C25—C26 | 109.4 |
C2—C3—H3 | 122.2 | N3—C26—C25 | 110.0 (3) |
C2—C3—C4 | 115.7 (4) | N3—C26—H26A | 109.7 |
H3—C3—C4 | 122.2 | N3—C26—H26B | 109.7 |
C3—C4—H4 | 118.9 | C25—C26—H26A | 109.7 |
C3—C4—C5 | 122.1 (4) | C25—C26—H26B | 109.7 |
H4—C4—C5 | 118.9 | H26A—C26—H26B | 108.2 |
C4—C5—H5 | 119.5 | N3—C27—H27A | 109.6 |
C4—C5—C6 | 121.1 (4) | N3—C27—H27B | 109.6 |
H5—C5—C6 | 119.5 | N3—C27—C28 | 110.4 (3) |
C5—C6—H6 | 121.5 | H27A—C27—H27B | 108.1 |
C5—C6—C7 | 117.0 (4) | H27A—C27—C28 | 109.6 |
H6—C6—C7 | 121.5 | H27B—C27—C28 | 109.6 |
C2—C7—C6 | 122.0 (4) | C24—C28—C27 | 111.2 (3) |
C2—C7—C8 | 108.6 (3) | C24—C28—H28A | 109.4 |
C6—C7—C8 | 129.4 (4) | C24—C28—H28B | 109.4 |
O2—C8—N1 | 125.1 (3) | C27—C28—H28A | 109.4 |
O2—C8—C7 | 129.2 (3) | C27—C28—H28B | 109.4 |
N1—C8—C7 | 105.6 (3) | H28A—C28—H28B | 108.0 |
N1—C9—H9 | 107.2 | N3—C29—H29A | 109.3 |
N1—C9—C10 | 112.4 (3) | N3—C29—H29B | 109.3 |
N1—C9—C17 | 110.6 (3) | N3—C29—C30 | 111.6 (3) |
H9—C9—C10 | 107.2 | H29A—C29—H29B | 108.0 |
H9—C9—C17 | 107.2 | H29A—C29—C30 | 109.3 |
C10—C9—C17 | 111.8 (3) | H29B—C29—C30 | 109.3 |
C9—C10—H10A | 108.9 | C29—C30—H30A | 109.0 |
C9—C10—H10B | 108.9 | C29—C30—H30B | 109.0 |
C9—C10—C11 | 113.5 (3) | C29—C30—C31 | 113.1 (3) |
H10A—C10—H10B | 107.7 | H30A—C30—H30B | 107.8 |
H10A—C10—C11 | 108.9 | H30A—C30—C31 | 109.0 |
H10B—C10—C11 | 108.9 | H30B—C30—C31 | 109.0 |
C10—C11—C12 | 122.1 (4) | C30—C31—C32 | 121.7 (5) |
C10—C11—C16 | 120.4 (4) | C30—C31—C36 | 121.3 (5) |
C12—C11—C16 | 117.5 (4) | C32—C31—C36 | 117.0 (4) |
C11—C12—H12 | 119.4 | C31—C32—H32 | 118.6 |
C11—C12—C13 | 121.2 (4) | C31—C32—C33 | 122.8 (5) |
H12—C12—C13 | 119.4 | H32—C32—C33 | 118.6 |
C12—C13—H13 | 120.5 | C32—C33—H33 | 120.2 |
C12—C13—C14 | 119.1 (4) | C32—C33—C34 | 119.5 (5) |
H13—C13—C14 | 120.5 | H33—C33—C34 | 120.2 |
C13—C14—H14 | 120.0 | C33—C34—H34 | 119.4 |
C13—C14—C15 | 120.0 (4) | C33—C34—C35 | 121.1 (5) |
H14—C14—C15 | 120.0 | H34—C34—C35 | 119.4 |
C14—C15—H15 | 119.9 | C34—C35—H35 | 120.3 |
C14—C15—C16 | 120.2 (5) | C34—C35—C36 | 119.3 (5) |
H15—C15—C16 | 119.9 | H35—C35—C36 | 120.3 |
C11—C16—C15 | 122.0 (4) | C31—C36—C35 | 120.3 (5) |
C11—C16—H16 | 119.0 | C31—C36—H36 | 119.9 |
C15—C16—H16 | 119.0 | C35—C36—H36 | 119.9 |
O3—C17—N2 | 121.5 (3) | O4—C37—H37A | 109.5 |
O3—C17—C9 | 121.7 (4) | O4—C37—H37B | 109.5 |
N2—C17—C9 | 116.8 (3) | O4—C37—H37C | 109.5 |
N2—C18—C19 | 120.8 (3) | H37A—C37—H37B | 109.5 |
N2—C18—C23 | 120.1 (3) | H37A—C37—H37C | 109.5 |
C19—C18—C23 | 119.1 (4) | H37B—C37—H37C | 109.5 |
C18—C19—H19 | 119.9 | O5—C38—H38A | 109.5 |
C18—C19—C20 | 120.2 (4) | O5—C38—H38B | 109.5 |
H19—C19—C20 | 119.9 | O5—C38—H38C | 109.5 |
C19—C20—H20 | 119.6 | H38A—C38—H38B | 109.5 |
C19—C20—C21 | 120.8 (4) | H38A—C38—H38C | 109.5 |
H20—C20—C21 | 119.6 | H38B—C38—H38C | 109.5 |
C20—C21—H21 | 120.1 | ||
C8—N1—C1—O1 | 176.0 (4) | C24—N2—C17—O3 | −2.8 (5) |
C8—N1—C1—C2 | −3.2 (4) | C24—N2—C17—C9 | 176.9 (3) |
C9—N1—C1—O1 | −1.2 (6) | N1—C9—C17—O3 | −121.7 (4) |
C9—N1—C1—C2 | 179.6 (3) | N1—C9—C17—N2 | 58.5 (4) |
O1—C1—C2—C3 | 3.9 (7) | C10—C9—C17—O3 | 4.4 (5) |
O1—C1—C2—C7 | −175.9 (4) | C10—C9—C17—N2 | −175.4 (3) |
N1—C1—C2—C3 | −177.1 (4) | C17—N2—C18—C19 | 72.5 (5) |
N1—C1—C2—C7 | 3.2 (4) | C17—N2—C18—C23 | −109.6 (4) |
C1—C2—C3—C4 | −178.5 (4) | C24—N2—C18—C19 | −90.4 (4) |
C7—C2—C3—C4 | 1.2 (6) | C24—N2—C18—C23 | 87.5 (4) |
C2—C3—C4—C5 | −0.4 (7) | N2—C18—C19—C20 | 179.3 (4) |
C3—C4—C5—C6 | 0.0 (7) | C23—C18—C19—C20 | 1.4 (6) |
C4—C5—C6—C7 | −0.3 (7) | C18—C19—C20—C21 | −2.4 (6) |
C1—C2—C7—C6 | 178.2 (4) | C19—C20—C21—C22 | 1.8 (6) |
C1—C2—C7—C8 | −2.1 (4) | C20—C21—C22—C23 | −0.2 (6) |
C3—C2—C7—C6 | −1.6 (6) | C21—C22—C23—C18 | −0.7 (6) |
C3—C2—C7—C8 | 178.1 (4) | N2—C18—C23—C22 | −177.7 (4) |
C5—C6—C7—C2 | 1.1 (6) | C19—C18—C23—C22 | 0.2 (6) |
C5—C6—C7—C8 | −178.6 (4) | C17—N2—C24—C25 | 155.9 (3) |
C1—N1—C8—O2 | 179.8 (4) | C17—N2—C24—C28 | −80.1 (4) |
C1—N1—C8—C7 | 1.9 (4) | C18—N2—C24—C25 | −40.3 (4) |
C9—N1—C8—O2 | −3.0 (6) | C18—N2—C24—C28 | 83.8 (4) |
C9—N1—C8—C7 | 179.1 (3) | N2—C24—C25—C26 | 179.4 (3) |
C2—C7—C8—O2 | −177.5 (4) | C28—C24—C25—C26 | 55.2 (4) |
C2—C7—C8—N1 | 0.2 (4) | C27—N3—C26—C25 | 60.1 (4) |
C6—C7—C8—O2 | 2.2 (7) | C29—N3—C26—C25 | −174.4 (3) |
C6—C7—C8—N1 | 179.9 (4) | C24—C25—C26—N3 | −58.7 (4) |
C1—N1—C9—C10 | 107.3 (4) | C26—N3—C27—C28 | −59.2 (4) |
C1—N1—C9—C17 | −127.0 (4) | C29—N3—C27—C28 | 176.1 (3) |
C8—N1—C9—C10 | −69.6 (4) | N2—C24—C28—C27 | −179.5 (3) |
C8—N1—C9—C17 | 56.2 (5) | C25—C24—C28—C27 | −54.0 (4) |
N1—C9—C10—C11 | −53.0 (4) | N3—C27—C28—C24 | 56.4 (4) |
C17—C9—C10—C11 | −178.1 (3) | C26—N3—C29—C30 | 168.2 (4) |
C9—C10—C11—C12 | −61.5 (5) | C27—N3—C29—C30 | −67.9 (5) |
C9—C10—C11—C16 | 118.3 (4) | N3—C29—C30—C31 | −174.0 (4) |
C10—C11—C12—C13 | −179.9 (4) | C29—C30—C31—C32 | −82.3 (6) |
C16—C11—C12—C13 | 0.3 (6) | C29—C30—C31—C36 | 99.6 (5) |
C11—C12—C13—C14 | −0.2 (7) | C30—C31—C32—C33 | −178.5 (4) |
C12—C13—C14—C15 | 0.6 (7) | C36—C31—C32—C33 | −0.3 (6) |
C13—C14—C15—C16 | −1.1 (8) | C31—C32—C33—C34 | 1.6 (7) |
C10—C11—C16—C15 | 179.3 (4) | C32—C33—C34—C35 | −1.2 (7) |
C12—C11—C16—C15 | −0.9 (7) | C33—C34—C35—C36 | −0.5 (7) |
C14—C15—C16—C11 | 1.3 (8) | C30—C31—C36—C35 | 176.8 (4) |
C18—N2—C17—O3 | −165.6 (3) | C32—C31—C36—C35 | −1.4 (6) |
C18—N2—C17—C9 | 14.2 (5) | C34—C35—C36—C31 | 1.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O5 | 0.83 (1) | 2.03 (4) | 2.769 (6) | 148 (7) |
O5—H5O···Cli | 0.82 (1) | 2.34 (3) | 3.092 (3) | 152 (5) |
N3—H3N···Cl | 0.98 (4) | 2.07 (4) | 3.041 (4) | 170 (3) |
Symmetry code: (i) x−1, y, z. |