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Crystals of the title compound, C
16H
30N
2O
5, were successfully grown from an ethyl acetate solution. There are two independent molecules in the asymmetric unit. One molecule has a
cis and the other a
trans conformation at the urethane linkage, –O—CO—NH–. Independent molecules are linked into chains by NH
O=C and OH
O=C hydrogen bonds along the
c axis.
Supporting information
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.
tert-butoxycarbonyl-
L-
allo-isoleucyl-N-
α-methyl-
L-valine
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
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