Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601110X/ac2010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601110X/ac2010Isup2.hkl |
CCDC reference: 604947
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C22H19N3O2 | Dx = 1.239 Mg m−3 |
Mr = 357.40 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 2824 reflections |
a = 11.713 (1) Å | θ = 2.3–24.9° |
b = 14.951 (1) Å | µ = 0.08 mm−1 |
c = 21.877 (2) Å | T = 298 K |
V = 3831.1 (5) Å3 | Block, yellow |
Z = 8 | 0.30 × 0.17 × 0.10 mm |
F(000) = 1504 |
Bruker SMART CCD area-detector diffractometer | 7941 independent reflections |
Radiation source: fine-focus sealed tube | 4828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 26.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.976, Tmax = 0.992 | k = −18→18 |
29274 measured reflections | l = −27→27 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.0909P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
7941 reflections | Δρmax = 0.32 e Å−3 |
492 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (2) |
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 | ||
O1 | 0.4986 (3) | 0.4407 (2) | 0.39088 (17) | 0.0716 (10) | |
H1 | 0.5623 | 0.4411 | 0.4065 | 0.107* | |
O2 | 0.8274 (3) | 0.24940 (15) | 0.52372 (16) | 0.0581 (10) | |
O3 | 0.7437 (3) | 0.0598 (2) | 0.17357 (17) | 0.0733 (10) | |
H3 | 0.7990 | 0.0582 | 0.1506 | 0.110* | |
O4 | 1.0713 (3) | 0.25090 (15) | 0.04195 (17) | 0.0623 (10) | |
N1 | 0.6663 (2) | 0.3787 (2) | 0.44958 (14) | 0.0484 (7) | |
N2 | 0.8834 (3) | 0.47425 (17) | 0.54214 (14) | 0.0522 (8) | |
N3 | 0.9123 (3) | 0.38358 (18) | 0.54892 (15) | 0.0529 (8) | |
N4 | 0.9098 (3) | 0.1211 (2) | 0.11165 (15) | 0.0507 (8) | |
N5 | 1.1240 (3) | 0.02692 (18) | 0.01714 (15) | 0.0537 (8) | |
N6 | 1.1531 (3) | 0.11739 (19) | 0.01070 (16) | 0.0555 (9) | |
C1 | 0.5324 (3) | 0.2843 (3) | 0.39861 (18) | 0.0432 (9) | |
C2 | 0.4672 (3) | 0.3559 (3) | 0.37953 (17) | 0.0522 (10) | |
C3 | 0.3658 (4) | 0.3422 (4) | 0.3478 (2) | 0.0626 (12) | |
H3A | 0.3220 | 0.3912 | 0.3361 | 0.075* | |
C4 | 0.3300 (4) | 0.2591 (3) | 0.3338 (2) | 0.0604 (14) | |
H4 | 0.2621 | 0.2520 | 0.3123 | 0.072* | |
C5 | 0.3925 (3) | 0.1827 (3) | 0.35072 (18) | 0.0510 (11) | |
C6 | 0.3585 (4) | 0.0967 (3) | 0.33524 (19) | 0.0653 (12) | |
H6 | 0.2897 | 0.0891 | 0.3147 | 0.078* | |
C7 | 0.4221 (4) | 0.0229 (3) | 0.3490 (2) | 0.0713 (13) | |
H7 | 0.3984 | −0.0339 | 0.3373 | 0.086* | |
C8 | 0.5239 (4) | 0.0355 (3) | 0.3812 (2) | 0.0724 (14) | |
H8 | 0.5679 | −0.0143 | 0.3911 | 0.087* | |
C9 | 0.5605 (3) | 0.1167 (3) | 0.3983 (2) | 0.0563 (10) | |
H9 | 0.6282 | 0.1217 | 0.4203 | 0.068* | |
C10 | 0.4974 (3) | 0.1959 (3) | 0.38331 (19) | 0.0490 (10) | |
C11 | 0.6342 (3) | 0.2981 (2) | 0.43532 (17) | 0.0447 (9) | |
H11 | 0.6764 | 0.2492 | 0.4487 | 0.054* | |
C12 | 0.7611 (3) | 0.3958 (2) | 0.48612 (16) | 0.0448 (9) | |
C13 | 0.7976 (3) | 0.4771 (3) | 0.50101 (19) | 0.0450 (10) | |
C14 | 0.7563 (4) | 0.5674 (3) | 0.4780 (2) | 0.0674 (12) | |
H14A | 0.8192 | 0.6085 | 0.4767 | 0.101* | |
H14B | 0.6985 | 0.5900 | 0.5050 | 0.101* | |
H14C | 0.7251 | 0.5607 | 0.4377 | 0.101* | |
C15 | 0.9715 (4) | 0.5396 (3) | 0.5513 (3) | 0.0743 (15) | |
H15A | 1.0219 | 0.5396 | 0.5167 | 0.111* | |
H15B | 1.0138 | 0.5251 | 0.5875 | 0.111* | |
H15C | 0.9376 | 0.5977 | 0.5557 | 0.111* | |
C16 | 0.8316 (3) | 0.3310 (2) | 0.51801 (18) | 0.0485 (9) | |
C17 | 0.9718 (3) | 0.3562 (2) | 0.60279 (19) | 0.0504 (9) | |
C18 | 0.9366 (4) | 0.3844 (3) | 0.6594 (2) | 0.0681 (12) | |
H18 | 0.8728 | 0.4210 | 0.6632 | 0.082* | |
C19 | 0.9954 (5) | 0.3585 (4) | 0.7103 (3) | 0.0945 (17) | |
H19 | 0.9731 | 0.3787 | 0.7487 | 0.113* | |
C20 | 1.0888 (6) | 0.3019 (4) | 0.7044 (3) | 0.102 (2) | |
H20 | 1.1263 | 0.2808 | 0.7390 | 0.123* | |
C21 | 1.1255 (5) | 0.2770 (4) | 0.6467 (4) | 0.100 (2) | |
H21 | 1.1914 | 0.2429 | 0.6425 | 0.120* | |
C22 | 1.0658 (4) | 0.3022 (3) | 0.5962 (2) | 0.0702 (13) | |
H22 | 1.0885 | 0.2830 | 0.5576 | 0.084* | |
C23 | 0.7772 (3) | 0.2179 (3) | 0.16267 (18) | 0.0461 (10) | |
C24 | 0.7135 (4) | 0.1471 (3) | 0.1838 (2) | 0.0579 (11) | |
C25 | 0.6123 (4) | 0.1616 (3) | 0.2169 (2) | 0.0643 (13) | |
H25 | 0.5708 | 0.1128 | 0.2310 | 0.077* | |
C26 | 0.5744 (4) | 0.2450 (3) | 0.2286 (2) | 0.0595 (15) | |
H26 | 0.5056 | 0.2525 | 0.2492 | 0.071* | |
C27 | 0.6374 (4) | 0.3218 (3) | 0.2100 (2) | 0.0545 (11) | |
C28 | 0.6025 (4) | 0.4086 (3) | 0.22507 (19) | 0.0630 (12) | |
H28 | 0.5360 | 0.4172 | 0.2475 | 0.076* | |
C29 | 0.6645 (4) | 0.4800 (3) | 0.2072 (2) | 0.0715 (13) | |
H29 | 0.6402 | 0.5376 | 0.2167 | 0.086* | |
C30 | 0.7643 (4) | 0.4671 (3) | 0.1749 (2) | 0.0623 (12) | |
H30 | 0.8070 | 0.5166 | 0.1630 | 0.075* | |
C31 | 0.8020 (4) | 0.3833 (3) | 0.1597 (2) | 0.0594 (11) | |
H31 | 0.8697 | 0.3769 | 0.1378 | 0.071* | |
C32 | 0.7408 (3) | 0.3079 (3) | 0.17648 (19) | 0.0448 (9) | |
C33 | 0.8790 (3) | 0.2011 (3) | 0.12645 (16) | 0.0469 (9) | |
H33 | 0.9231 | 0.2493 | 0.1136 | 0.056* | |
C34 | 1.0042 (3) | 0.1058 (2) | 0.07410 (17) | 0.0453 (9) | |
C35 | 1.0389 (3) | 0.0210 (3) | 0.05805 (19) | 0.0482 (10) | |
C36 | 0.9970 (4) | −0.0664 (3) | 0.0808 (2) | 0.0627 (12) | |
H36A | 1.0008 | −0.1098 | 0.0485 | 0.094* | |
H36B | 0.9193 | −0.0603 | 0.0942 | 0.094* | |
H36C | 1.0436 | −0.0857 | 0.1144 | 0.094* | |
C37 | 1.2108 (4) | −0.0400 (3) | 0.0045 (3) | 0.0666 (14) | |
H37A | 1.2741 | −0.0317 | 0.0317 | 0.100* | |
H37B | 1.2364 | −0.0339 | −0.0370 | 0.100* | |
H37C | 1.1792 | −0.0986 | 0.0103 | 0.100* | |
C38 | 1.0738 (3) | 0.1693 (2) | 0.04304 (18) | 0.0486 (9) | |
C39 | 1.2126 (3) | 0.1467 (2) | −0.04194 (18) | 0.0493 (9) | |
C40 | 1.1767 (4) | 0.1229 (3) | −0.0991 (2) | 0.0759 (13) | |
H40 | 1.1131 | 0.0865 | −0.1042 | 0.091* | |
C41 | 1.2375 (6) | 0.1542 (4) | −0.1496 (3) | 0.1062 (19) | |
H41 | 1.2158 | 0.1378 | −0.1889 | 0.127* | |
C42 | 1.3302 (6) | 0.2097 (4) | −0.1407 (3) | 0.111 (2) | |
H42 | 1.3696 | 0.2314 | −0.1745 | 0.133* | |
C43 | 1.3639 (6) | 0.2327 (4) | −0.0853 (4) | 0.102 (2) | |
H43 | 1.4255 | 0.2714 | −0.0805 | 0.122* | |
C44 | 1.3079 (4) | 0.1993 (3) | −0.0344 (2) | 0.0716 (13) | |
H44 | 1.3346 | 0.2123 | 0.0047 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.069 (2) | 0.0581 (19) | 0.087 (3) | 0.0147 (15) | −0.0120 (19) | −0.0064 (18) |
O2 | 0.075 (2) | 0.0323 (19) | 0.067 (2) | −0.0052 (11) | −0.0225 (19) | −0.0010 (12) |
O3 | 0.072 (2) | 0.063 (2) | 0.086 (3) | −0.0239 (16) | 0.0155 (18) | −0.0013 (18) |
O4 | 0.080 (2) | 0.0324 (19) | 0.075 (3) | 0.0040 (12) | 0.021 (2) | −0.0039 (12) |
N1 | 0.0505 (18) | 0.0481 (18) | 0.0467 (18) | 0.0005 (14) | 0.0020 (16) | −0.0024 (14) |
N2 | 0.062 (2) | 0.0295 (17) | 0.065 (2) | 0.0007 (15) | −0.0068 (18) | −0.0054 (16) |
N3 | 0.068 (2) | 0.0321 (16) | 0.059 (2) | −0.0025 (15) | −0.0155 (18) | 0.0008 (14) |
N4 | 0.0487 (19) | 0.0477 (19) | 0.056 (2) | −0.0047 (15) | 0.0012 (17) | −0.0063 (15) |
N5 | 0.064 (2) | 0.0345 (18) | 0.063 (2) | 0.0026 (16) | 0.0088 (18) | −0.0091 (16) |
N6 | 0.064 (2) | 0.0346 (17) | 0.068 (2) | −0.0005 (15) | 0.0140 (19) | −0.0071 (15) |
C1 | 0.042 (2) | 0.049 (2) | 0.039 (2) | −0.0014 (18) | 0.0046 (18) | 0.0028 (19) |
C2 | 0.050 (2) | 0.062 (3) | 0.044 (2) | 0.007 (2) | 0.0034 (19) | 0.001 (2) |
C3 | 0.043 (2) | 0.096 (4) | 0.049 (3) | 0.014 (2) | 0.000 (2) | −0.002 (3) |
C4 | 0.044 (3) | 0.100 (4) | 0.038 (3) | 0.006 (2) | −0.004 (2) | −0.001 (2) |
C5 | 0.042 (2) | 0.077 (3) | 0.033 (2) | −0.011 (2) | 0.0058 (19) | −0.007 (2) |
C6 | 0.049 (2) | 0.096 (4) | 0.051 (3) | −0.018 (3) | −0.002 (2) | −0.012 (3) |
C7 | 0.081 (3) | 0.070 (3) | 0.062 (3) | −0.022 (3) | 0.001 (3) | −0.018 (2) |
C8 | 0.070 (3) | 0.058 (3) | 0.089 (4) | −0.002 (2) | 0.000 (3) | −0.008 (3) |
C9 | 0.054 (2) | 0.055 (2) | 0.060 (2) | −0.0033 (19) | −0.013 (2) | −0.002 (2) |
C10 | 0.040 (2) | 0.063 (3) | 0.044 (2) | −0.0003 (19) | 0.0040 (18) | 0.004 (2) |
C11 | 0.0363 (19) | 0.046 (2) | 0.052 (2) | −0.0021 (16) | 0.0000 (17) | 0.0024 (17) |
C12 | 0.049 (2) | 0.044 (2) | 0.042 (2) | 0.0039 (17) | −0.0014 (17) | −0.0065 (16) |
C13 | 0.046 (2) | 0.040 (2) | 0.048 (2) | 0.0071 (17) | 0.0008 (19) | 0.0077 (18) |
C14 | 0.077 (3) | 0.043 (2) | 0.082 (3) | 0.009 (2) | −0.003 (2) | 0.002 (2) |
C15 | 0.078 (3) | 0.045 (3) | 0.100 (4) | −0.010 (2) | −0.017 (3) | −0.017 (3) |
C16 | 0.051 (2) | 0.040 (2) | 0.054 (2) | −0.0052 (17) | −0.0019 (19) | −0.0020 (18) |
C17 | 0.052 (2) | 0.040 (2) | 0.060 (3) | −0.0020 (17) | −0.008 (2) | 0.0024 (19) |
C18 | 0.073 (3) | 0.067 (3) | 0.064 (3) | 0.002 (2) | 0.006 (3) | −0.008 (2) |
C19 | 0.129 (5) | 0.097 (4) | 0.057 (3) | −0.001 (4) | −0.014 (3) | 0.007 (3) |
C20 | 0.135 (5) | 0.079 (4) | 0.093 (4) | 0.001 (4) | −0.053 (4) | 0.018 (3) |
C21 | 0.099 (5) | 0.074 (3) | 0.127 (6) | 0.016 (3) | −0.041 (4) | 0.004 (4) |
C22 | 0.072 (3) | 0.056 (3) | 0.083 (3) | 0.013 (2) | −0.011 (3) | −0.011 (2) |
C23 | 0.033 (2) | 0.068 (3) | 0.037 (2) | −0.008 (2) | −0.0051 (17) | −0.007 (2) |
C24 | 0.049 (2) | 0.068 (3) | 0.057 (3) | −0.011 (2) | −0.006 (2) | −0.007 (2) |
C25 | 0.054 (3) | 0.080 (3) | 0.059 (3) | −0.024 (2) | 0.001 (2) | 0.016 (3) |
C26 | 0.030 (3) | 0.095 (4) | 0.053 (3) | −0.002 (2) | −0.001 (2) | 0.007 (2) |
C27 | 0.044 (2) | 0.080 (3) | 0.040 (2) | 0.002 (2) | 0.000 (2) | 0.010 (2) |
C28 | 0.053 (3) | 0.085 (3) | 0.050 (3) | 0.017 (2) | −0.003 (2) | −0.005 (2) |
C29 | 0.075 (3) | 0.071 (3) | 0.069 (3) | 0.021 (3) | −0.009 (3) | −0.008 (3) |
C30 | 0.073 (3) | 0.056 (3) | 0.058 (3) | 0.016 (2) | 0.007 (2) | 0.004 (2) |
C31 | 0.054 (3) | 0.064 (3) | 0.060 (3) | 0.001 (2) | 0.006 (2) | −0.003 (2) |
C32 | 0.042 (2) | 0.057 (2) | 0.035 (2) | −0.0032 (19) | −0.0047 (18) | 0.0028 (19) |
C33 | 0.048 (2) | 0.051 (3) | 0.041 (2) | −0.0070 (18) | −0.0027 (17) | −0.0046 (17) |
C34 | 0.050 (2) | 0.035 (2) | 0.051 (2) | −0.0013 (17) | −0.0034 (18) | −0.0015 (16) |
C35 | 0.053 (2) | 0.042 (2) | 0.050 (3) | −0.0052 (18) | −0.010 (2) | −0.0118 (18) |
C36 | 0.072 (3) | 0.040 (2) | 0.077 (3) | −0.0121 (19) | −0.010 (2) | 0.0049 (19) |
C37 | 0.069 (3) | 0.040 (2) | 0.090 (4) | 0.008 (2) | 0.014 (3) | −0.002 (2) |
C38 | 0.053 (2) | 0.037 (2) | 0.056 (2) | 0.0028 (17) | 0.0045 (19) | −0.0048 (18) |
C39 | 0.054 (2) | 0.038 (2) | 0.055 (3) | 0.0039 (17) | 0.011 (2) | −0.0080 (18) |
C40 | 0.077 (3) | 0.083 (3) | 0.068 (3) | −0.005 (2) | 0.005 (3) | 0.005 (3) |
C41 | 0.155 (6) | 0.101 (4) | 0.063 (3) | 0.007 (4) | 0.008 (4) | 0.003 (3) |
C42 | 0.149 (6) | 0.081 (4) | 0.102 (5) | −0.013 (4) | 0.065 (5) | 0.010 (4) |
C43 | 0.112 (5) | 0.068 (3) | 0.126 (6) | −0.030 (3) | 0.058 (4) | −0.022 (4) |
C44 | 0.076 (3) | 0.056 (3) | 0.083 (3) | −0.013 (2) | 0.015 (3) | −0.011 (2) |
O1—C2 | 1.343 (5) | C17—C22 | 1.373 (6) |
O1—H1 | 0.8200 | C18—C19 | 1.364 (7) |
O2—C16 | 1.228 (4) | C18—H18 | 0.9300 |
O3—C24 | 1.371 (5) | C19—C20 | 1.389 (8) |
O3—H3 | 0.8200 | C19—H19 | 0.9300 |
O4—C38 | 1.220 (4) | C20—C21 | 1.383 (9) |
N1—C11 | 1.300 (4) | C20—H20 | 0.9300 |
N1—C12 | 1.392 (5) | C21—C22 | 1.361 (8) |
N2—C13 | 1.350 (5) | C21—H21 | 0.9300 |
N2—N3 | 1.405 (4) | C22—H22 | 0.9300 |
N2—C15 | 1.434 (5) | C23—C24 | 1.375 (6) |
N3—C16 | 1.403 (5) | C23—C32 | 1.444 (6) |
N3—C17 | 1.429 (5) | C23—C33 | 1.453 (5) |
N4—C33 | 1.290 (4) | C24—C25 | 1.405 (6) |
N4—C34 | 1.396 (5) | C25—C26 | 1.348 (6) |
N5—C35 | 1.343 (5) | C25—H25 | 0.9300 |
N5—N6 | 1.402 (4) | C26—C27 | 1.424 (6) |
N5—C37 | 1.452 (5) | C26—H26 | 0.9300 |
N6—C38 | 1.402 (5) | C27—C28 | 1.400 (6) |
N6—C39 | 1.416 (5) | C27—C32 | 1.432 (6) |
C1—C2 | 1.380 (5) | C28—C29 | 1.349 (6) |
C1—C10 | 1.423 (5) | C28—H28 | 0.9300 |
C1—C11 | 1.452 (5) | C29—C30 | 1.380 (6) |
C2—C3 | 1.390 (6) | C29—H29 | 0.9300 |
C3—C4 | 1.347 (6) | C30—C31 | 1.369 (6) |
C3—H3A | 0.9300 | C30—H30 | 0.9300 |
C4—C5 | 1.406 (6) | C31—C32 | 1.386 (5) |
C4—H4 | 0.9300 | C31—H31 | 0.9300 |
C5—C6 | 1.388 (6) | C33—H33 | 0.9300 |
C5—C10 | 1.434 (6) | C34—C35 | 1.378 (5) |
C6—C7 | 1.365 (6) | C34—C38 | 1.425 (5) |
C6—H6 | 0.9300 | C35—C36 | 1.482 (5) |
C7—C8 | 1.398 (6) | C36—H36A | 0.9600 |
C7—H7 | 0.9300 | C36—H36B | 0.9600 |
C8—C9 | 1.341 (6) | C36—H36C | 0.9600 |
C8—H8 | 0.9300 | C37—H37A | 0.9600 |
C9—C10 | 1.435 (5) | C37—H37B | 0.9600 |
C9—H9 | 0.9300 | C37—H37C | 0.9600 |
C11—H11 | 0.9300 | C39—C40 | 1.366 (6) |
C12—C13 | 1.329 (5) | C39—C44 | 1.376 (6) |
C12—C16 | 1.452 (5) | C40—C41 | 1.396 (7) |
C13—C14 | 1.519 (5) | C40—H40 | 0.9300 |
C14—H14A | 0.9600 | C41—C42 | 1.380 (8) |
C14—H14B | 0.9600 | C41—H41 | 0.9300 |
C14—H14C | 0.9600 | C42—C43 | 1.320 (9) |
C15—H15A | 0.9600 | C42—H42 | 0.9300 |
C15—H15B | 0.9600 | C43—C44 | 1.387 (8) |
C15—H15C | 0.9600 | C43—H43 | 0.9300 |
C17—C18 | 1.372 (6) | C44—H44 | 0.9300 |
C2—O1—H1 | 109.5 | C21—C20—H20 | 120.3 |
C24—O3—H3 | 109.5 | C19—C20—H20 | 120.3 |
C11—N1—C12 | 122.7 (3) | C22—C21—C20 | 120.5 (5) |
C13—N2—N3 | 106.3 (3) | C22—C21—H21 | 119.7 |
C13—N2—C15 | 127.3 (4) | C20—C21—H21 | 119.7 |
N3—N2—C15 | 118.0 (3) | C21—C22—C17 | 119.3 (5) |
C16—N3—N2 | 109.1 (3) | C21—C22—H22 | 120.4 |
C16—N3—C17 | 124.5 (3) | C17—C22—H22 | 120.4 |
N2—N3—C17 | 118.7 (3) | C24—C23—C32 | 119.1 (4) |
C33—N4—C34 | 121.4 (3) | C24—C23—C33 | 119.8 (4) |
C35—N5—N6 | 108.1 (3) | C32—C23—C33 | 121.2 (4) |
C35—N5—C37 | 126.9 (4) | O3—C24—C23 | 122.5 (4) |
N6—N5—C37 | 118.4 (3) | O3—C24—C25 | 116.7 (4) |
N5—N6—C38 | 108.9 (3) | C23—C24—C25 | 120.9 (4) |
N5—N6—C39 | 120.0 (3) | C26—C25—C24 | 121.2 (4) |
C38—N6—C39 | 124.4 (3) | C26—C25—H25 | 119.4 |
C2—C1—C10 | 119.3 (4) | C24—C25—H25 | 119.4 |
C2—C1—C11 | 120.8 (3) | C25—C26—C27 | 121.4 (4) |
C10—C1—C11 | 119.9 (4) | C25—C26—H26 | 119.3 |
O1—C2—C1 | 121.6 (4) | C27—C26—H26 | 119.3 |
O1—C2—C3 | 117.7 (4) | C28—C27—C26 | 122.0 (4) |
C1—C2—C3 | 120.6 (4) | C28—C27—C32 | 120.2 (4) |
C4—C3—C2 | 121.0 (5) | C26—C27—C32 | 117.8 (4) |
C4—C3—H3A | 119.5 | C29—C28—C27 | 120.5 (4) |
C2—C3—H3A | 119.5 | C29—C28—H28 | 119.7 |
C3—C4—C5 | 121.8 (4) | C27—C28—H28 | 119.7 |
C3—C4—H4 | 119.1 | C28—C29—C30 | 119.6 (4) |
C5—C4—H4 | 119.1 | C28—C29—H29 | 120.2 |
C6—C5—C4 | 122.6 (4) | C30—C29—H29 | 120.2 |
C6—C5—C10 | 119.6 (4) | C31—C30—C29 | 121.8 (5) |
C4—C5—C10 | 117.7 (4) | C31—C30—H30 | 119.1 |
C7—C6—C5 | 122.6 (4) | C29—C30—H30 | 119.1 |
C7—C6—H6 | 118.7 | C30—C31—C32 | 120.9 (4) |
C5—C6—H6 | 118.7 | C30—C31—H31 | 119.6 |
C6—C7—C8 | 117.9 (4) | C32—C31—H31 | 119.6 |
C6—C7—H7 | 121.0 | C31—C32—C27 | 117.1 (4) |
C8—C7—H7 | 121.0 | C31—C32—C23 | 123.4 (4) |
C9—C8—C7 | 122.3 (5) | C27—C32—C23 | 119.6 (4) |
C9—C8—H8 | 118.8 | N4—C33—C23 | 121.8 (4) |
C7—C8—H8 | 118.8 | N4—C33—H33 | 119.1 |
C8—C9—C10 | 121.3 (4) | C23—C33—H33 | 119.1 |
C8—C9—H9 | 119.4 | C35—C34—N4 | 122.3 (3) |
C10—C9—H9 | 119.4 | C35—C34—C38 | 108.8 (3) |
C1—C10—C5 | 119.4 (4) | N4—C34—C38 | 128.7 (3) |
C1—C10—C9 | 124.3 (4) | N5—C35—C34 | 109.2 (4) |
C5—C10—C9 | 116.2 (4) | N5—C35—C36 | 121.9 (4) |
N1—C11—C1 | 120.1 (3) | C34—C35—C36 | 128.9 (4) |
N1—C11—H11 | 119.9 | C35—C36—H36A | 109.5 |
C1—C11—H11 | 119.9 | C35—C36—H36B | 109.5 |
C13—C12—N1 | 124.5 (3) | H36A—C36—H36B | 109.5 |
C13—C12—C16 | 108.0 (3) | C35—C36—H36C | 109.5 |
N1—C12—C16 | 127.3 (3) | H36A—C36—H36C | 109.5 |
C12—C13—N2 | 111.9 (3) | H36B—C36—H36C | 109.5 |
C12—C13—C14 | 128.9 (4) | N5—C37—H37A | 109.5 |
N2—C13—C14 | 119.1 (4) | N5—C37—H37B | 109.5 |
C13—C14—H14A | 109.5 | H37A—C37—H37B | 109.5 |
C13—C14—H14B | 109.5 | N5—C37—H37C | 109.5 |
H14A—C14—H14B | 109.5 | H37A—C37—H37C | 109.5 |
C13—C14—H14C | 109.5 | H37B—C37—H37C | 109.5 |
H14A—C14—H14C | 109.5 | O4—C38—N6 | 124.0 (4) |
H14B—C14—H14C | 109.5 | O4—C38—C34 | 131.4 (4) |
N2—C15—H15A | 109.5 | N6—C38—C34 | 104.5 (3) |
N2—C15—H15B | 109.5 | C40—C39—C44 | 120.6 (4) |
H15A—C15—H15B | 109.5 | C40—C39—N6 | 120.8 (4) |
N2—C15—H15C | 109.5 | C44—C39—N6 | 118.6 (4) |
H15A—C15—H15C | 109.5 | C39—C40—C41 | 118.7 (5) |
H15B—C15—H15C | 109.5 | C39—C40—H40 | 120.6 |
O2—C16—N3 | 122.3 (4) | C41—C40—H40 | 120.6 |
O2—C16—C12 | 133.6 (4) | C42—C41—C40 | 119.5 (6) |
N3—C16—C12 | 104.0 (3) | C42—C41—H41 | 120.3 |
C18—C17—C22 | 121.1 (4) | C40—C41—H41 | 120.3 |
C18—C17—N3 | 120.7 (4) | C43—C42—C41 | 121.4 (5) |
C22—C17—N3 | 118.2 (4) | C43—C42—H42 | 119.3 |
C19—C18—C17 | 119.8 (4) | C41—C42—H42 | 119.3 |
C19—C18—H18 | 120.1 | C42—C43—C44 | 120.2 (5) |
C17—C18—H18 | 120.1 | C42—C43—H43 | 119.9 |
C18—C19—C20 | 119.7 (5) | C44—C43—H43 | 119.9 |
C18—C19—H19 | 120.1 | C39—C44—C43 | 119.5 (5) |
C20—C19—H19 | 120.1 | C39—C44—H44 | 120.2 |
C21—C20—C19 | 119.5 (5) | C43—C44—H44 | 120.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N4 | 0.82 | 1.82 | 2.541 (4) | 147 |
O1—H1···N1 | 0.82 | 1.80 | 2.523 (4) | 146 |