Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028089/is6011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028089/is6011Isup2.hkl |
CCDC reference: 259556
Data collection: RAPID-AUTO (Rigaku/MSC, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.
C17H32N2O5 | F(000) = 752.00 |
Mr = 344.45 | Dx = 1.111 Mg m−3 |
Monoclinic, P21 | Melting point = 408–409 K |
Hall symbol: P 2yb | Cu Kα radiation, λ = 1.54180 Å |
a = 6.359 (2) Å | Cell parameters from 2607 reflections |
b = 21.158 (5) Å | θ = 3.6–67.6° |
c = 15.374 (5) Å | µ = 0.67 mm−1 |
β = 95.43 (2)° | T = 173 K |
V = 2059.2 (11) Å3 | Needle, colorless |
Z = 4 | 0.40 × 0.05 × 0.05 mm |
Rigaku R-AXIS RAPID diffractometer | 1729 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.053 |
ω scans | θmax = 68.1° |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983) | h = −7→7 |
Tmin = 0.810, Tmax = 0.967 | k = −25→24 |
18832 measured reflections | l = −18→17 |
3748 independent reflections |
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[0.0003Fo2 + 1.5σ(Fo2)]/(4Fo2) |
wR(F2) = 0.116 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.59 e Å−3 |
3748 reflections | Δρmin = −0.39 e Å−3 |
377 parameters |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O111 | 0.2677 (7) | 0.2749 (2) | −0.0882 (3) | 0.035 (1) | |
O112 | 0.4182 (7) | 0.2547 (2) | −0.2141 (3) | 0.035 (1) | |
O121 | 0.7652 (8) | 0.2074 (2) | 0.0252 (3) | 0.053 (2) | |
O131 | 0.9664 (9) | 0.1869 (4) | 0.2665 (3) | 0.116 (3) | |
O132 | 0.6793 (7) | 0.2052 (3) | 0.3267 (3) | 0.055 (2) | |
O211 | 0.3316 (7) | 0.0709 (2) | 0.3385 (3) | 0.054 (2) | |
O212 | 0.3916 (7) | 0.0619 (2) | 0.4865 (3) | 0.039 (2) | |
O221 | −0.1823 (7) | 0.1484 (2) | 0.4748 (3) | 0.039 (2) | |
O231 | −0.2976 (8) | 0.1165 (2) | 0.7816 (3) | 0.054 (2) | |
O232 | −0.3642 (6) | 0.1897 (2) | 0.6770 (3) | 0.035 (1) | |
N121 | 0.4465 (8) | 0.1859 (3) | −0.1001 (3) | 0.036 (2) | |
N131 | 0.5484 (8) | 0.2144 (3) | 0.1333 (3) | 0.031 (2) | |
N221 | 0.2313 (8) | 0.1485 (3) | 0.4212 (3) | 0.035 (2) | |
N231 | −0.0231 (8) | 0.1233 (3) | 0.6086 (3) | 0.026 (2) | |
C111 | 0.117 (1) | 0.3226 (4) | −0.1241 (4) | 0.041 (2)* | |
C112 | 0.013 (1) | 0.3458 (3) | −0.0446 (4) | 0.054 (2)* | |
C113 | 0.235 (1) | 0.3765 (4) | −0.1612 (4) | 0.064 (2)* | |
C114 | −0.042 (1) | 0.2928 (4) | −0.1901 (4) | 0.055 (2)* | |
C115 | 0.381 (1) | 0.2393 (3) | −0.1387 (5) | 0.031 (2) | |
C121 | 0.413 (1) | 0.1694 (3) | −0.0110 (4) | 0.036 (2) | |
C122 | 0.593 (1) | 0.1985 (3) | 0.0508 (4) | 0.037 (2) | |
C123 | 0.399 (1) | 0.0972 (3) | 0.0004 (4) | 0.043 (2)* | |
C124 | 0.607 (1) | 0.0632 (4) | −0.0059 (5) | 0.067 (2)* | |
C125 | 0.215 (1) | 0.0722 (4) | −0.0632 (5) | 0.071 (3)* | |
C126 | 0.141 (1) | 0.0055 (4) | −0.0419 (6) | 0.093 (3)* | |
C131 | 0.709 (1) | 0.2507 (4) | 0.1875 (4) | 0.035 (2) | |
C132 | 0.801 (1) | 0.2102 (4) | 0.2657 (4) | 0.042 (2) | |
C133 | 0.628 (1) | 0.3159 (3) | 0.2142 (4) | 0.045 (2)* | |
C134 | 0.541 (1) | 0.3522 (4) | 0.1326 (4) | 0.065 (2)* | |
C135 | 0.810 (1) | 0.3532 (4) | 0.2647 (5) | 0.078 (3)* | |
C136 | 0.3454 (9) | 0.2043 (3) | 0.1678 (4) | 0.040 (2)* | |
C211 | 0.444 (1) | 0.0110 (4) | 0.3178 (5) | 0.054 (2)* | |
C212 | 0.383 (1) | 0.0067 (4) | 0.2201 (6) | 0.098 (3)* | |
C213 | 0.676 (1) | 0.0200 (4) | 0.3382 (5) | 0.065 (2)* | |
C214 | 0.351 (1) | −0.0440 (4) | 0.3624 (5) | 0.089 (3)* | |
C215 | 0.324 (1) | 0.0910 (4) | 0.4221 (4) | 0.032 (2) | |
C221 | 0.186 (1) | 0.1787 (3) | 0.5013 (4) | 0.025 (2) | |
C222 | −0.022 (1) | 0.1490 (3) | 0.5272 (4) | 0.032 (2) | |
C223 | 0.157 (1) | 0.2500 (3) | 0.4900 (4) | 0.036 (2)* | |
C224 | 0.366 (1) | 0.2786 (4) | 0.4626 (5) | 0.070 (3)* | |
C225 | 0.092 (1) | 0.2789 (4) | 0.5738 (4) | 0.051 (2)* | |
C226 | 0.040 (1) | 0.3496 (4) | 0.5647 (5) | 0.080 (3)* | |
C231 | −0.213 (1) | 0.0940 (3) | 0.6356 (4) | 0.028 (2) | |
C232 | −0.298 (1) | 0.1333 (4) | 0.7062 (4) | 0.032 (2) | |
C233 | −0.177 (1) | 0.0233 (3) | 0.6623 (4) | 0.038 (2)* | |
C234 | −0.073 (1) | −0.0119 (3) | 0.5914 (4) | 0.048 (2)* | |
C235 | −0.385 (1) | −0.0091 (3) | 0.6773 (5) | 0.052 (2)* | |
C236 | 0.1591 (9) | 0.1245 (3) | 0.6755 (4) | 0.039 (2)* | |
H3 | −0.1117 | 0.3199 | −0.0373 | 0.065* | |
H4 | −0.0288 | 0.3900 | −0.0532 | 0.065* | |
H5 | 0.1135 | 0.3421 | 0.0076 | 0.065* | |
H6 | 0.2697 | 0.4083 | −0.1158 | 0.077* | |
H7 | 0.1470 | 0.3956 | −0.2099 | 0.077* | |
H8 | 0.3660 | 0.3605 | −0.1823 | 0.077* | |
H9 | 0.0089 | 0.2948 | −0.2482 | 0.066* | |
H10 | −0.1769 | 0.3154 | −0.1910 | 0.066* | |
H11 | −0.0630 | 0.2485 | −0.1742 | 0.066* | |
H12 | 0.2792 | 0.1883 | 0.0028 | 0.044* | |
H13 | 0.3586 | 0.0897 | 0.0596 | 0.052* | |
H14 | 0.6192 | 0.0513 | −0.0668 | 0.080* | |
H15 | 0.6118 | 0.0251 | 0.0305 | 0.080* | |
H16 | 0.7239 | 0.0911 | 0.0146 | 0.080* | |
H17 | 0.0954 | 0.1011 | −0.0619 | 0.085* | |
H18 | 0.2626 | 0.0716 | −0.1221 | 0.085* | |
H19 | 0.2217 | −0.0257 | −0.0720 | 0.112* | |
H20 | −0.0097 | 0.0012 | −0.0614 | 0.112* | |
H21 | 0.1629 | −0.0015 | 0.0213 | 0.112* | |
H22 | 0.8254 | 0.2586 | 0.1513 | 0.042* | |
H23 | 0.5146 | 0.3100 | 0.2522 | 0.053* | |
H24 | 0.6554 | 0.3769 | 0.1105 | 0.078* | |
H25 | 0.4286 | 0.3807 | 0.1474 | 0.078* | |
H26 | 0.4849 | 0.3222 | 0.0877 | 0.078* | |
H27 | 0.8120 | 0.3442 | 0.3273 | 0.093* | |
H28 | 0.7881 | 0.3986 | 0.2548 | 0.093* | |
H29 | 0.9446 | 0.3403 | 0.2441 | 0.093* | |
H30 | 0.2557 | 0.2415 | 0.1557 | 0.048* | |
H31 | 0.3679 | 0.1975 | 0.2311 | 0.048* | |
H32 | 0.2764 | 0.1671 | 0.1399 | 0.048* | |
H33 | 0.2517 | −0.0174 | 0.2095 | 0.117* | |
H34 | 0.4955 | −0.0146 | 0.1917 | 0.118* | |
H35 | 0.3624 | 0.0494 | 0.1960 | 0.117* | |
H36 | 0.7369 | 0.0363 | 0.2864 | 0.078* | |
H37 | 0.7422 | −0.0204 | 0.3555 | 0.078* | |
H38 | 0.7010 | 0.0504 | 0.3862 | 0.078* | |
H39 | 0.4253 | −0.0498 | 0.4205 | 0.106* | |
H40 | 0.3642 | −0.0824 | 0.3276 | 0.107* | |
H41 | 0.2009 | −0.0357 | 0.3680 | 0.106* | |
H42 | 0.3003 | 0.1702 | 0.5470 | 0.030* | |
H43 | 0.0447 | 0.2576 | 0.4431 | 0.043* | |
H44 | 0.4575 | 0.2905 | 0.5149 | 0.084* | |
H45 | 0.3341 | 0.3161 | 0.4264 | 0.084* | |
H46 | 0.4379 | 0.2472 | 0.4291 | 0.084* | |
H47 | −0.0332 | 0.2567 | 0.5902 | 0.061* | |
H48 | 0.2083 | 0.2734 | 0.6199 | 0.061* | |
H49 | 0.1689 | 0.3742 | 0.5803 | 0.096* | |
H50 | −0.0668 | 0.3607 | 0.6040 | 0.096* | |
H51 | −0.0141 | 0.3591 | 0.5044 | 0.096* | |
H52 | −0.3190 | 0.0946 | 0.5849 | 0.034* | |
H53 | −0.0830 | 0.0216 | 0.7166 | 0.045* | |
H54 | −0.1820 | −0.0295 | 0.5488 | 0.057* | |
H55 | 0.0145 | −0.0462 | 0.6178 | 0.058* | |
H56 | 0.0159 | 0.0175 | 0.5617 | 0.057* | |
H57 | −0.4108 | −0.0045 | 0.7388 | 0.062* | |
H58 | −0.3763 | −0.0540 | 0.6627 | 0.062* | |
H59 | −0.5008 | 0.0106 | 0.6403 | 0.062* | |
H60 | 0.2453 | 0.0867 | 0.6696 | 0.047* | |
H61 | 0.1087 | 0.1253 | 0.7338 | 0.047* | |
H62 | 0.2445 | 0.1623 | 0.6675 | 0.047* | |
H121 | 0.5224 | 0.1557 | −0.1339 | 0.043* | |
H132 | 0.7513 | 0.1904 | 0.3657 | 0.066* | |
H221 | 0.1940 | 0.1699 | 0.3653 | 0.043* | |
H232 | −0.4315 | 0.2109 | 0.7094 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O111 | 0.049 (3) | 0.031 (3) | 0.026 (3) | 0.012 (3) | 0.013 (2) | −0.003 (2) |
O112 | 0.045 (3) | 0.043 (3) | 0.018 (2) | 0.003 (3) | 0.011 (2) | 0.001 (2) |
O121 | 0.051 (3) | 0.077 (4) | 0.035 (3) | −0.014 (3) | 0.019 (3) | −0.007 (3) |
O131 | 0.081 (5) | 0.215 (9) | 0.057 (4) | 0.090 (6) | 0.037 (4) | 0.065 (5) |
O132 | 0.038 (3) | 0.095 (5) | 0.033 (3) | 0.014 (3) | 0.011 (3) | 0.030 (3) |
O211 | 0.067 (4) | 0.068 (4) | 0.024 (3) | 0.042 (3) | −0.002 (3) | −0.011 (3) |
O212 | 0.047 (3) | 0.045 (3) | 0.025 (3) | 0.003 (3) | 0.000 (2) | 0.004 (2) |
O221 | 0.031 (3) | 0.062 (4) | 0.023 (3) | −0.006 (3) | −0.004 (2) | 0.010 (3) |
O231 | 0.081 (4) | 0.065 (4) | 0.018 (3) | 0.028 (3) | 0.012 (3) | 0.010 (3) |
O232 | 0.044 (3) | 0.031 (3) | 0.031 (3) | 0.004 (3) | 0.009 (2) | 0.000 (2) |
N121 | 0.049 (4) | 0.032 (4) | 0.027 (3) | 0.004 (3) | 0.012 (3) | −0.004 (3) |
N131 | 0.035 (4) | 0.039 (4) | 0.020 (3) | −0.004 (3) | 0.010 (3) | −0.006 (3) |
N221 | 0.049 (4) | 0.039 (4) | 0.019 (3) | 0.015 (3) | 0.014 (3) | 0.008 (3) |
N231 | 0.023 (3) | 0.033 (4) | 0.024 (3) | −0.000 (3) | 0.004 (3) | 0.001 (3) |
C115 | 0.018 (4) | 0.032 (5) | 0.042 (5) | −0.000 (4) | −0.001 (4) | −0.003 (4) |
C121 | 0.057 (5) | 0.036 (5) | 0.017 (4) | 0.002 (4) | 0.017 (4) | −0.005 (3) |
C122 | 0.054 (5) | 0.028 (5) | 0.030 (4) | 0.002 (4) | 0.011 (4) | 0.005 (4) |
C131 | 0.025 (4) | 0.063 (6) | 0.019 (4) | 0.003 (4) | 0.005 (3) | 0.003 (4) |
C132 | 0.041 (5) | 0.051 (6) | 0.034 (4) | 0.008 (5) | 0.012 (4) | 0.011 (4) |
C215 | 0.029 (4) | 0.043 (5) | 0.027 (4) | −0.007 (4) | 0.015 (4) | −0.004 (4) |
C221 | 0.030 (4) | 0.026 (4) | 0.020 (4) | −0.001 (4) | 0.012 (3) | −0.004 (3) |
C222 | 0.055 (5) | 0.021 (4) | 0.024 (4) | 0.012 (4) | 0.023 (4) | −0.001 (3) |
C231 | 0.032 (4) | 0.030 (4) | 0.023 (4) | 0.002 (4) | 0.004 (3) | −0.001 (3) |
C232 | 0.018 (4) | 0.047 (6) | 0.031 (4) | −0.004 (4) | 0.002 (3) | 0.003 (4) |
O111—C111 | 1.465 (8) | C113—H8 | 0.9800 |
O111—C115 | 1.338 (8) | C114—H9 | 0.9800 |
O112—C115 | 1.249 (8) | C114—H10 | 0.9800 |
O121—C122 | 1.212 (9) | C114—H11 | 0.9800 |
O131—C132 | 1.160 (10) | C121—H12 | 0.9800 |
O132—C132 | 1.275 (9) | C123—H13 | 0.9800 |
O211—C211 | 1.505 (9) | C124—H14 | 0.9801 |
O211—C215 | 1.359 (8) | C124—H15 | 0.9800 |
O212—C215 | 1.210 (8) | C124—H16 | 0.9800 |
O221—C222 | 1.236 (8) | C125—H17 | 0.9799 |
O231—C232 | 1.211 (8) | C125—H18 | 0.9800 |
O232—C232 | 1.329 (9) | C126—H19 | 0.9800 |
N121—C115 | 1.325 (9) | C126—H20 | 0.9800 |
N121—C121 | 1.449 (8) | C126—H21 | 0.9800 |
N131—C122 | 1.367 (8) | C131—H22 | 0.9800 |
N131—C131 | 1.473 (8) | C133—H23 | 0.9800 |
N131—C136 | 1.458 (8) | C134—H24 | 0.9801 |
N221—C215 | 1.352 (9) | C134—H25 | 0.9801 |
N221—C221 | 1.441 (8) | C134—H26 | 0.9801 |
N231—C222 | 1.366 (8) | C135—H27 | 0.9799 |
N231—C231 | 1.454 (8) | C135—H28 | 0.9801 |
N231—C236 | 1.475 (7) | C135—H29 | 0.9800 |
C111—C112 | 1.526 (9) | C136—H30 | 0.9801 |
C111—C113 | 1.507 (11) | C136—H31 | 0.9800 |
C111—C114 | 1.503 (9) | C136—H32 | 0.9800 |
C121—C122 | 1.545 (9) | C212—H33 | 0.9800 |
C121—C123 | 1.541 (9) | C212—H34 | 0.9801 |
C123—C124 | 1.522 (9) | C212—H35 | 0.9800 |
C123—C125 | 1.545 (10) | C213—H36 | 0.9800 |
C125—C126 | 1.533 (12) | C213—H37 | 0.9800 |
C131—C132 | 1.545 (9) | C213—H38 | 0.9800 |
C131—C133 | 1.544 (10) | C214—H39 | 0.9800 |
C133—C134 | 1.530 (9) | C214—H40 | 0.9801 |
C133—C135 | 1.547 (10) | C214—H41 | 0.9800 |
C211—C212 | 1.519 (12) | C221—H42 | 0.9799 |
C211—C213 | 1.493 (9) | C223—H43 | 0.9800 |
C211—C214 | 1.496 (11) | C224—H44 | 0.9800 |
C221—C222 | 1.550 (9) | C224—H45 | 0.9800 |
C221—C223 | 1.526 (9) | C224—H46 | 0.9800 |
C223—C221 | 1.526 (9) | C225—H47 | 0.9800 |
C223—C224 | 1.555 (9) | C225—H48 | 0.9800 |
C223—C225 | 1.517 (9) | C226—H49 | 0.9800 |
C224—C223 | 1.555 (9) | C226—H50 | 0.9801 |
C225—C223 | 1.517 (9) | C226—H51 | 0.9800 |
C225—C226 | 1.535 (12) | C231—H52 | 0.9800 |
C231—C232 | 1.508 (9) | C233—H53 | 0.9800 |
C231—C233 | 1.562 (9) | C234—H54 | 0.9801 |
C233—C234 | 1.523 (9) | C234—H55 | 0.9799 |
C233—C235 | 1.526 (9) | C234—H56 | 0.9801 |
C234—C233 | 1.523 (9) | C235—H57 | 0.9800 |
O132—H132 | 0.7834 | C235—H58 | 0.9800 |
O232—H232 | 0.8200 | C235—H59 | 0.9800 |
N121—H121 | 0.9800 | C236—H60 | 0.9799 |
N221—H221 | 0.9799 | C236—H61 | 0.9800 |
C112—H3 | 0.9800 | C236—H62 | 0.9800 |
C112—H4 | 0.9799 | H43—C223 | 0.9800 |
C112—H5 | 0.9800 | H54—C234 | 0.9801 |
C113—H6 | 0.9800 | H55—C234 | 0.9799 |
C113—H7 | 0.9801 | H56—C234 | 0.9801 |
O111—C111—C112 | 103.7 (5) | H12—C121—C123 | 108.4328 |
O111—C111—C113 | 109.3 (5) | C121—C123—H13 | 106.7967 |
O111—C111—C114 | 109.9 (6) | C123—C124—H16 | 109.6197 |
C115—O111—C111 | 122.6 (5) | H13—C123—C124 | 106.6687 |
O111—C115—O112 | 123.5 (6) | C123—C124—H14 | 109.4726 |
O111—C115—N121 | 112.6 (6) | C123—C124—H15 | 109.6063 |
O112—C115—N121 | 124.0 (6) | C123—C125—H17 | 108.3821 |
O121—C122—C121 | 120.2 (6) | C123—C125—H18 | 108.1667 |
O121—C122—N131 | 122.3 (6) | H13—C123—C125 | 106.7237 |
O131—C132—C131 | 121.2 (7) | H16—C124—H14 | 109.4753 |
O131—C132—O132 | 124.7 (7) | H15—C124—H14 | 109.4085 |
O132—C132—C131 | 114.1 (6) | H16—C124—H15 | 109.2446 |
O211—C211—C212 | 100.2 (6) | H17—C125—C126 | 108.1736 |
O211—C211—C213 | 109.3 (6) | H18—C125—C126 | 108.3687 |
O211—C211—C214 | 109.8 (6) | C125—C126—H21 | 109.4795 |
C215—O211—C211 | 121.5 (5) | C125—C126—H19 | 109.3856 |
O211—C215—O212 | 125.0 (7) | C125—C126—H20 | 109.5073 |
O211—C215—N221 | 109.0 (6) | H18—C125—H17 | 109.4652 |
O212—C215—N221 | 125.9 (6) | H21—C126—H19 | 109.4753 |
O221—C222—C221 | 120.5 (5) | H20—C126—H19 | 109.4574 |
O221—C222—N231 | 121.3 (6) | H21—C126—H20 | 109.5221 |
O231—C232—C231 | 123.9 (6) | H22—C131—C132 | 106.7520 |
O231—C232—O232 | 124.0 (6) | H22—C131—C133 | 106.7218 |
O232—C232—C231 | 112.0 (5) | C131—C133—H23 | 109.1061 |
C121—N121—C115 | 124.1 (6) | H23—C133—C134 | 108.8573 |
N121—C121—C122 | 108.5 (5) | C133—C134—H26 | 109.4161 |
N121—C121—C123 | 111.2 (5) | C133—C134—H24 | 109.2460 |
N131—C122—C121 | 117.4 (6) | C133—C134—H25 | 109.5920 |
C131—N131—C122 | 117.3 (5) | H23—C133—C135 | 108.9184 |
C136—N131—C122 | 124.8 (5) | C133—C135—H27 | 109.5346 |
N131—C131—C132 | 110.0 (6) | C133—C135—H29 | 109.2093 |
N131—C131—C133 | 112.6 (5) | C133—C135—H28 | 109.4751 |
C136—N131—C131 | 117.5 (5) | H26—C134—H24 | 109.4733 |
C221—N221—C215 | 120.9 (5) | H25—C134—H24 | 109.5218 |
N221—C221—C222 | 106.5 (5) | H26—C134—H25 | 109.5776 |
N221—C221—C223 | 111.9 (5) | H29—C135—H27 | 109.4748 |
N231—C222—C221 | 118.3 (5) | H28—C135—H27 | 109.4735 |
C231—N231—C222 | 120.4 (5) | H29—C135—H28 | 109.6598 |
C236—N231—C222 | 124.2 (5) | H31—C136—H30 | 109.5050 |
N231—C231—C232 | 109.6 (5) | H32—C136—H30 | 109.4780 |
N231—C231—C233 | 112.1 (5) | H32—C136—H31 | 109.5131 |
C236—N231—C231 | 115.4 (5) | C211—C212—H33 | 109.2703 |
C113—C111—C112 | 109.3 (6) | C211—C212—H35 | 109.3605 |
C114—C111—C112 | 111.2 (6) | C211—C212—H34 | 109.7826 |
C114—C111—C113 | 113.0 (5) | C211—C213—H36 | 109.5048 |
C123—C121—C122 | 111.9 (5) | C211—C213—H38 | 109.2669 |
C121—C123—C125 | 108.5 (5) | C211—C213—H37 | 109.7014 |
C121—C123—C124 | 113.6 (6) | C211—C214—H39 | 109.5477 |
C125—C123—C124 | 114.0 (6) | C211—C214—H41 | 109.3646 |
C123—C125—C126 | 114.2 (6) | C211—C214—H40 | 109.5189 |
C133—C131—C132 | 113.6 (5) | H35—C212—H33 | 109.4745 |
C131—C133—C134 | 109.6 (5) | H34—C212—H33 | 109.4892 |
C131—C133—C135 | 109.7 (6) | H35—C212—H34 | 109.4497 |
C135—C133—C134 | 110.6 (6) | H38—C213—H36 | 109.4735 |
C213—C211—C212 | 111.8 (7) | H37—C213—H36 | 109.5459 |
C214—C211—C212 | 109.2 (6) | H38—C213—H37 | 109.3342 |
C214—C211—C213 | 115.5 (6) | H41—C214—H39 | 109.4702 |
C223—C221—C222 | 109.5 (5) | H40—C214—H39 | 109.4500 |
C221—C223—C224 | 108.6 (6) | H41—C214—H40 | 109.4759 |
C221—C223—C225 | 109.9 (5) | H42—C221—C222 | 109.6144 |
C225—C223—C224 | 112.4 (6) | H42—C221—C223 | 109.5952 |
C223—C225—C226 | 112.9 (6) | C221—C223—H43 | 108.4718 |
C233—C231—C232 | 113.1 (5) | C223—C224—H46 | 109.4399 |
C231—C233—C234 | 110.1 (5) | H43—C223—C224 | 108.5887 |
C231—C233—C235 | 111.2 (5) | C223—C224—H44 | 109.5769 |
C235—C233—C234 | 109.3 (5) | C223—C224—H45 | 109.5491 |
H132—O132—C132 | 104.2114 | H43—C223—C225 | 108.7077 |
H232—O232—C232 | 116.7971 | C223—C225—H47 | 108.5442 |
H121—N121—C115 | 118.0068 | C223—C225—H48 | 108.6487 |
N121—C121—H12 | 108.3786 | H46—C224—H44 | 109.4698 |
H121—N121—C121 | 117.9162 | H45—C224—H44 | 109.4162 |
N131—C131—H22 | 106.6753 | H46—C224—H45 | 109.3753 |
N131—C136—H31 | 109.4108 | H47—C225—C226 | 108.4536 |
N131—C136—H30 | 109.4029 | H48—C225—C226 | 108.7486 |
N131—C136—H32 | 109.5174 | C225—C226—H49 | 109.0712 |
H221—N221—C215 | 119.5022 | C225—C226—H51 | 109.8485 |
H221—N221—C221 | 119.5899 | C225—C226—H50 | 109.5193 |
N221—C221—H42 | 109.6533 | H48—C225—H47 | 109.4551 |
N231—C231—H52 | 107.1065 | H51—C226—H49 | 109.4735 |
N231—C236—H61 | 109.5250 | H50—C226—H49 | 109.5866 |
N231—C236—H60 | 109.2712 | H51—C226—H50 | 109.3284 |
N231—C236—H62 | 109.5820 | H52—C231—C232 | 107.4437 |
C111—C112—H3 | 109.2695 | H52—C231—C233 | 107.1467 |
C111—C112—H5 | 109.5519 | C231—C233—H53 | 108.7817 |
C111—C112—H4 | 109.4369 | C233—C234—H56 | 109.3953 |
C111—C113—H6 | 109.6080 | H53—C233—C234 | 108.6683 |
C111—C113—H8 | 109.5476 | C233—C234—H54 | 109.5880 |
C111—C113—H7 | 109.2860 | C233—C234—H55 | 109.5211 |
C111—C114—H9 | 109.6206 | H53—C233—C235 | 108.7831 |
C111—C114—H11 | 109.2778 | C233—C235—H57 | 109.1681 |
C111—C114—H10 | 109.5624 | C233—C235—H59 | 109.6322 |
H5—C112—H3 | 109.4694 | C233—C235—H58 | 109.4549 |
H4—C112—H3 | 109.6067 | H56—C234—H54 | 109.4678 |
H5—C112—H4 | 109.4927 | H55—C234—H54 | 109.4366 |
H8—C113—H6 | 109.4724 | H56—C234—H55 | 109.4184 |
H7—C113—H6 | 109.4615 | H59—C235—H57 | 109.4720 |
H8—C113—H7 | 109.4515 | H58—C235—H57 | 109.5736 |
H11—C114—H9 | 109.4836 | H59—C235—H58 | 109.5261 |
H10—C114—H9 | 109.3743 | H61—C236—H60 | 109.4880 |
H11—C114—H10 | 109.5087 | H62—C236—H60 | 109.4706 |
H12—C121—C122 | 108.2631 | H62—C236—H61 | 109.4903 |
C115—O111—C111—C112 | 174.7 (5) | N121—C121—C122—N131 | 150.6 (6) |
C115—O111—C111—C113 | −68.8 (7) | C123—C121—C122—O121 | 94.9 (7) |
C115—O111—C111—C114 | 55.7 (7) | C123—C121—C122—N131 | −86.3 (7) |
C111—O111—C115—O112 | 22.1 (9) | N121—C121—C123—C124 | 69.5 (7) |
C111—O111—C115—N121 | −157.2 (5) | N121—C121—C123—C125 | −58.5 (7) |
C215—O211—C211—C212 | 173.6 (5) | C122—C121—C123—C124 | −52.1 (7) |
C215—O211—C211—C213 | −68.8 (7) | C122—C121—C123—C125 | 179.9 (4) |
C215—O211—C211—C214 | 58.8 (7) | C121—C123—C125—C126 | −163.3 (6) |
C211—O211—C215—O212 | −5.2 (10) | C124—C123—C125—C126 | 68.9 (8) |
C211—O211—C215—N221 | 174.2 (5) | N131—C131—C132—O131 | 103.6 (8) |
C121—N121—C115—O111 | −4.0 (8) | N131—C131—C132—O132 | −76.3 (8) |
C121—N121—C115—O112 | 176.6 (6) | C133—C131—C132—O131 | −129.1 (8) |
C115—N121—C121—C122 | −85.7 (7) | C133—C131—C132—O132 | 51.0 (8) |
C115—N121—C121—C123 | 150.8 (6) | N131—C131—C133—C134 | −54.1 (7) |
C131—N131—C122—O121 | 7.8 (9) | N131—C131—C133—C135 | −175.7 (6) |
C131—N131—C122—C121 | −171.1 (5) | C132—C131—C133—C134 | −180.0 (5) |
C136—N131—C122—O121 | −179.3 (6) | C132—C131—C133—C135 | 58.4 (7) |
C136—N131—C122—C121 | 1.8 (9) | N221—C221—C222—O221 | −54.0 (8) |
C122—N131—C131—C132 | −113.4 (6) | N221—C221—C222—N231 | 125.6 (6) |
C122—N131—C131—C133 | 118.7 (6) | C223—C221—C222—O221 | 67.1 (7) |
C136—N131—C131—C132 | 73.1 (7) | C223—C221—C222—N231 | −113.3 (6) |
C136—N131—C131—C133 | −54.7 (7) | N221—C221—C223—C224 | −61.2 (6) |
C221—N221—C215—O211 | 174.5 (5) | N221—C221—C223—C225 | 175.5 (5) |
C221—N221—C215—O212 | −5.6 (10) | C222—C221—C223—C224 | −179.0 (5) |
C215—N221—C221—C222 | −80.9 (6) | C222—C221—C223—C225 | 57.6 (6) |
C215—N221—C221—C223 | 159.5 (5) | C221—C223—C225—C226 | −174.6 (6) |
C231—N231—C222—O221 | 0.5 (8) | C224—C223—C225—C226 | 64.2 (7) |
C231—N231—C222—C221 | −179.1 (5) | N231—C231—C232—O231 | −111.2 (7) |
C236—N231—C222—O221 | −177.5 (6) | N231—C231—C232—O232 | 65.6 (6) |
C236—N231—C222—C221 | 2.9 (9) | C233—C231—C232—O231 | 14.7 (9) |
C222—N231—C231—C232 | −112.0 (6) | C233—C231—C232—O232 | −168.5 (5) |
C222—N231—C231—C233 | 121.5 (6) | N231—C231—C233—C234 | −50.4 (7) |
C236—N231—C231—C232 | 66.1 (6) | N231—C231—C233—C235 | −171.6 (5) |
C236—N231—C231—C233 | −60.3 (6) | C232—C231—C233—C234 | −174.9 (5) |
N121—C121—C122—O121 | −28.2 (9) | C232—C231—C233—C235 | 63.8 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N221—H221···O131i | 0.98 | 2.03 | 2.897 (7) | 147 |
O132—H132···O221ii | 0.78 | 1.91 | 2.650 (6) | 157 |
N121—H121···O231iii | 0.98 | 1.99 | 2.946 (7) | 164 |
O232—H232···O112iv | 0.82 | 1.84 | 2.656 (6) | 177 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y, z−1; (iv) x−1, y, z+1. |