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
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.010 Å
- R factor = 0.058
- wR factor = 0.116
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 24
Author Response: Because of the limited numbers of observed reflections. Even at the low temperature condition (173 K), diffractions from the crystal of (I) were too weak to collect enough numbers. Therefore only main-cain atoms were refefined anisotropically. |
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.92 Ratio
Author Response: It is due to the difference of thermal mobility. The chain end atoms often shows higer U(eq) compared with the atoms located inside of the chain. |
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
Author Response: Because of the weak reflections. Even at the low temperature condition (173 K), diffractions from the crystal of (I) were too weak to obtain enough intensities. |
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio
Author Response: It is due to the difference of thermal mobility. The chain end atoms often shows higer U(eq) compared with the atoms located inside of the chain. |
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.34 Ratio
Author Response: It is due to the difference of thermal mobility. The chain end atoms often shows higer U(eq) compared with the atoms located inside of the chain. |
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.93 Ratio
Author Response: It is due to the difference of thermal mobility. The chain end atoms often show higer U(eq) compared with the atoms located inside of the chain. |
PLAT230_ALERT_2_C Hirshfeld Test Diff for O221 - C222 .. 6.97 su
Author Response: This is due to a thermal vibration of the O=C group. For example, an out of plane motion of O=C away from the N-methyl amide plane can be expected. |
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C132
Author Response: It is due to the low mobility of C atoms which are located relatively inside of the chain. |
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C211
Author Response: It is due to the low mobility of C atoms which are located relatively inside of the chain. |
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.85
Author Response: It is due to the thermal mobility of C(141) and O(141). Atoms in the chain-end group often show higer U(eq) and larger U3/U1 ratio compared with the atoms located inside of the chain. |
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21
Author Response: It is due to the thermal mobility of C(141) and O(141). Atoms in the chain-end group often show higer U(eq) and larger U3/U1 ratio compared with the atoms located inside of the chain. |
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Author Response: It is due to the thermal mobility. A chain end atom often shows a lower bond precision compared with that of the inside of the chain. |
PLAT432_ALERT_2_C Short Inter X...Y Contact O131 .. C136 .. 2.99 Ang.
Author Response: An interaction, such as hydrogen bond, is expected between N-methyl N-CH3 and carbonyl O=C. |
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 68.12 From the CIF: _reflns_number_total 3748 Count of symmetry unique reflns 3880 Completeness (_total/calc) 96.60% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
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. |