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Crystals of the title compound, C16H30N2O5, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028089/is6011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028089/is6011Isup2.hkl
Contains datablock I

CCDC reference: 259556

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C17H32N2O5F(000) = 752.00
Mr = 344.45Dx = 1.111 Mg m3
Monoclinic, P21Melting point = 408–409 K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54180 Å
a = 6.359 (2) ÅCell parameters from 2607 reflections
b = 21.158 (5) Åθ = 3.6–67.6°
c = 15.374 (5) ŵ = 0.67 mm1
β = 95.43 (2)°T = 173 K
V = 2059.2 (11) Å3Needle, colorless
Z = 40.40 × 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-1Rint = 0.053
ω scansθmax = 68.1°
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
h = 77
Tmin = 0.810, Tmax = 0.967k = 2524
18832 measured reflectionsl = 1817
3748 independent reflections
Refinement top
Refinement on F2All 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 = 1.02Δρmax = 0.59 e Å3
3748 reflectionsΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
O1110.2677 (7)0.2749 (2)0.0882 (3)0.035 (1)
O1120.4182 (7)0.2547 (2)0.2141 (3)0.035 (1)
O1210.7652 (8)0.2074 (2)0.0252 (3)0.053 (2)
O1310.9664 (9)0.1869 (4)0.2665 (3)0.116 (3)
O1320.6793 (7)0.2052 (3)0.3267 (3)0.055 (2)
O2110.3316 (7)0.0709 (2)0.3385 (3)0.054 (2)
O2120.3916 (7)0.0619 (2)0.4865 (3)0.039 (2)
O2210.1823 (7)0.1484 (2)0.4748 (3)0.039 (2)
O2310.2976 (8)0.1165 (2)0.7816 (3)0.054 (2)
O2320.3642 (6)0.1897 (2)0.6770 (3)0.035 (1)
N1210.4465 (8)0.1859 (3)0.1001 (3)0.036 (2)
N1310.5484 (8)0.2144 (3)0.1333 (3)0.031 (2)
N2210.2313 (8)0.1485 (3)0.4212 (3)0.035 (2)
N2310.0231 (8)0.1233 (3)0.6086 (3)0.026 (2)
C1110.117 (1)0.3226 (4)0.1241 (4)0.041 (2)*
C1120.013 (1)0.3458 (3)0.0446 (4)0.054 (2)*
C1130.235 (1)0.3765 (4)0.1612 (4)0.064 (2)*
C1140.042 (1)0.2928 (4)0.1901 (4)0.055 (2)*
C1150.381 (1)0.2393 (3)0.1387 (5)0.031 (2)
C1210.413 (1)0.1694 (3)0.0110 (4)0.036 (2)
C1220.593 (1)0.1985 (3)0.0508 (4)0.037 (2)
C1230.399 (1)0.0972 (3)0.0004 (4)0.043 (2)*
C1240.607 (1)0.0632 (4)0.0059 (5)0.067 (2)*
C1250.215 (1)0.0722 (4)0.0632 (5)0.071 (3)*
C1260.141 (1)0.0055 (4)0.0419 (6)0.093 (3)*
C1310.709 (1)0.2507 (4)0.1875 (4)0.035 (2)
C1320.801 (1)0.2102 (4)0.2657 (4)0.042 (2)
C1330.628 (1)0.3159 (3)0.2142 (4)0.045 (2)*
C1340.541 (1)0.3522 (4)0.1326 (4)0.065 (2)*
C1350.810 (1)0.3532 (4)0.2647 (5)0.078 (3)*
C1360.3454 (9)0.2043 (3)0.1678 (4)0.040 (2)*
C2110.444 (1)0.0110 (4)0.3178 (5)0.054 (2)*
C2120.383 (1)0.0067 (4)0.2201 (6)0.098 (3)*
C2130.676 (1)0.0200 (4)0.3382 (5)0.065 (2)*
C2140.351 (1)0.0440 (4)0.3624 (5)0.089 (3)*
C2150.324 (1)0.0910 (4)0.4221 (4)0.032 (2)
C2210.186 (1)0.1787 (3)0.5013 (4)0.025 (2)
C2220.022 (1)0.1490 (3)0.5272 (4)0.032 (2)
C2230.157 (1)0.2500 (3)0.4900 (4)0.036 (2)*
C2240.366 (1)0.2786 (4)0.4626 (5)0.070 (3)*
C2250.092 (1)0.2789 (4)0.5738 (4)0.051 (2)*
C2260.040 (1)0.3496 (4)0.5647 (5)0.080 (3)*
C2310.213 (1)0.0940 (3)0.6356 (4)0.028 (2)
C2320.298 (1)0.1333 (4)0.7062 (4)0.032 (2)
C2330.177 (1)0.0233 (3)0.6623 (4)0.038 (2)*
C2340.073 (1)0.0119 (3)0.5914 (4)0.048 (2)*
C2350.385 (1)0.0091 (3)0.6773 (5)0.052 (2)*
C2360.1591 (9)0.1245 (3)0.6755 (4)0.039 (2)*
H30.11170.31990.03730.065*
H40.02880.39000.05320.065*
H50.11350.34210.00760.065*
H60.26970.40830.11580.077*
H70.14700.39560.20990.077*
H80.36600.36050.18230.077*
H90.00890.29480.24820.066*
H100.17690.31540.19100.066*
H110.06300.24850.17420.066*
H120.27920.18830.00280.044*
H130.35860.08970.05960.052*
H140.61920.05130.06680.080*
H150.61180.02510.03050.080*
H160.72390.09110.01460.080*
H170.09540.10110.06190.085*
H180.26260.07160.12210.085*
H190.22170.02570.07200.112*
H200.00970.00120.06140.112*
H210.16290.00150.02130.112*
H220.82540.25860.15130.042*
H230.51460.31000.25220.053*
H240.65540.37690.11050.078*
H250.42860.38070.14740.078*
H260.48490.32220.08770.078*
H270.81200.34420.32730.093*
H280.78810.39860.25480.093*
H290.94460.34030.24410.093*
H300.25570.24150.15570.048*
H310.36790.19750.23110.048*
H320.27640.16710.13990.048*
H330.25170.01740.20950.117*
H340.49550.01460.19170.118*
H350.36240.04940.19600.117*
H360.73690.03630.28640.078*
H370.74220.02040.35550.078*
H380.70100.05040.38620.078*
H390.42530.04980.42050.106*
H400.36420.08240.32760.107*
H410.20090.03570.36800.106*
H420.30030.17020.54700.030*
H430.04470.25760.44310.043*
H440.45750.29050.51490.084*
H450.33410.31610.42640.084*
H460.43790.24720.42910.084*
H470.03320.25670.59020.061*
H480.20830.27340.61990.061*
H490.16890.37420.58030.096*
H500.06680.36070.60400.096*
H510.01410.35910.50440.096*
H520.31900.09460.58490.034*
H530.08300.02160.71660.045*
H540.18200.02950.54880.057*
H550.01450.04620.61780.058*
H560.01590.01750.56170.057*
H570.41080.00450.73880.062*
H580.37630.05400.66270.062*
H590.50080.01060.64030.062*
H600.24530.08670.66960.047*
H610.10870.12530.73380.047*
H620.24450.16230.66750.047*
H1210.52240.15570.13390.043*
H1320.75130.19040.36570.066*
H2210.19400.16990.36530.043*
H2320.43150.21090.70940.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1110.049 (3)0.031 (3)0.026 (3)0.012 (3)0.013 (2)0.003 (2)
O1120.045 (3)0.043 (3)0.018 (2)0.003 (3)0.011 (2)0.001 (2)
O1210.051 (3)0.077 (4)0.035 (3)0.014 (3)0.019 (3)0.007 (3)
O1310.081 (5)0.215 (9)0.057 (4)0.090 (6)0.037 (4)0.065 (5)
O1320.038 (3)0.095 (5)0.033 (3)0.014 (3)0.011 (3)0.030 (3)
O2110.067 (4)0.068 (4)0.024 (3)0.042 (3)0.002 (3)0.011 (3)
O2120.047 (3)0.045 (3)0.025 (3)0.003 (3)0.000 (2)0.004 (2)
O2210.031 (3)0.062 (4)0.023 (3)0.006 (3)0.004 (2)0.010 (3)
O2310.081 (4)0.065 (4)0.018 (3)0.028 (3)0.012 (3)0.010 (3)
O2320.044 (3)0.031 (3)0.031 (3)0.004 (3)0.009 (2)0.000 (2)
N1210.049 (4)0.032 (4)0.027 (3)0.004 (3)0.012 (3)0.004 (3)
N1310.035 (4)0.039 (4)0.020 (3)0.004 (3)0.010 (3)0.006 (3)
N2210.049 (4)0.039 (4)0.019 (3)0.015 (3)0.014 (3)0.008 (3)
N2310.023 (3)0.033 (4)0.024 (3)0.000 (3)0.004 (3)0.001 (3)
C1150.018 (4)0.032 (5)0.042 (5)0.000 (4)0.001 (4)0.003 (4)
C1210.057 (5)0.036 (5)0.017 (4)0.002 (4)0.017 (4)0.005 (3)
C1220.054 (5)0.028 (5)0.030 (4)0.002 (4)0.011 (4)0.005 (4)
C1310.025 (4)0.063 (6)0.019 (4)0.003 (4)0.005 (3)0.003 (4)
C1320.041 (5)0.051 (6)0.034 (4)0.008 (5)0.012 (4)0.011 (4)
C2150.029 (4)0.043 (5)0.027 (4)0.007 (4)0.015 (4)0.004 (4)
C2210.030 (4)0.026 (4)0.020 (4)0.001 (4)0.012 (3)0.004 (3)
C2220.055 (5)0.021 (4)0.024 (4)0.012 (4)0.023 (4)0.001 (3)
C2310.032 (4)0.030 (4)0.023 (4)0.002 (4)0.004 (3)0.001 (3)
C2320.018 (4)0.047 (6)0.031 (4)0.004 (4)0.002 (3)0.003 (4)
Geometric parameters (Å, º) top
O111—C1111.465 (8)C113—H80.9800
O111—C1151.338 (8)C114—H90.9800
O112—C1151.249 (8)C114—H100.9800
O121—C1221.212 (9)C114—H110.9800
O131—C1321.160 (10)C121—H120.9800
O132—C1321.275 (9)C123—H130.9800
O211—C2111.505 (9)C124—H140.9801
O211—C2151.359 (8)C124—H150.9800
O212—C2151.210 (8)C124—H160.9800
O221—C2221.236 (8)C125—H170.9799
O231—C2321.211 (8)C125—H180.9800
O232—C2321.329 (9)C126—H190.9800
N121—C1151.325 (9)C126—H200.9800
N121—C1211.449 (8)C126—H210.9800
N131—C1221.367 (8)C131—H220.9800
N131—C1311.473 (8)C133—H230.9800
N131—C1361.458 (8)C134—H240.9801
N221—C2151.352 (9)C134—H250.9801
N221—C2211.441 (8)C134—H260.9801
N231—C2221.366 (8)C135—H270.9799
N231—C2311.454 (8)C135—H280.9801
N231—C2361.475 (7)C135—H290.9800
C111—C1121.526 (9)C136—H300.9801
C111—C1131.507 (11)C136—H310.9800
C111—C1141.503 (9)C136—H320.9800
C121—C1221.545 (9)C212—H330.9800
C121—C1231.541 (9)C212—H340.9801
C123—C1241.522 (9)C212—H350.9800
C123—C1251.545 (10)C213—H360.9800
C125—C1261.533 (12)C213—H370.9800
C131—C1321.545 (9)C213—H380.9800
C131—C1331.544 (10)C214—H390.9800
C133—C1341.530 (9)C214—H400.9801
C133—C1351.547 (10)C214—H410.9800
C211—C2121.519 (12)C221—H420.9799
C211—C2131.493 (9)C223—H430.9800
C211—C2141.496 (11)C224—H440.9800
C221—C2221.550 (9)C224—H450.9800
C221—C2231.526 (9)C224—H460.9800
C223—C2211.526 (9)C225—H470.9800
C223—C2241.555 (9)C225—H480.9800
C223—C2251.517 (9)C226—H490.9800
C224—C2231.555 (9)C226—H500.9801
C225—C2231.517 (9)C226—H510.9800
C225—C2261.535 (12)C231—H520.9800
C231—C2321.508 (9)C233—H530.9800
C231—C2331.562 (9)C234—H540.9801
C233—C2341.523 (9)C234—H550.9799
C233—C2351.526 (9)C234—H560.9801
C234—C2331.523 (9)C235—H570.9800
O132—H1320.7834C235—H580.9800
O232—H2320.8200C235—H590.9800
N121—H1210.9800C236—H600.9799
N221—H2210.9799C236—H610.9800
C112—H30.9800C236—H620.9800
C112—H40.9799H43—C2230.9800
C112—H50.9800H54—C2340.9801
C113—H60.9800H55—C2340.9799
C113—H70.9801H56—C2340.9801
O111—C111—C112103.7 (5)H12—C121—C123108.4328
O111—C111—C113109.3 (5)C121—C123—H13106.7967
O111—C111—C114109.9 (6)C123—C124—H16109.6197
C115—O111—C111122.6 (5)H13—C123—C124106.6687
O111—C115—O112123.5 (6)C123—C124—H14109.4726
O111—C115—N121112.6 (6)C123—C124—H15109.6063
O112—C115—N121124.0 (6)C123—C125—H17108.3821
O121—C122—C121120.2 (6)C123—C125—H18108.1667
O121—C122—N131122.3 (6)H13—C123—C125106.7237
O131—C132—C131121.2 (7)H16—C124—H14109.4753
O131—C132—O132124.7 (7)H15—C124—H14109.4085
O132—C132—C131114.1 (6)H16—C124—H15109.2446
O211—C211—C212100.2 (6)H17—C125—C126108.1736
O211—C211—C213109.3 (6)H18—C125—C126108.3687
O211—C211—C214109.8 (6)C125—C126—H21109.4795
C215—O211—C211121.5 (5)C125—C126—H19109.3856
O211—C215—O212125.0 (7)C125—C126—H20109.5073
O211—C215—N221109.0 (6)H18—C125—H17109.4652
O212—C215—N221125.9 (6)H21—C126—H19109.4753
O221—C222—C221120.5 (5)H20—C126—H19109.4574
O221—C222—N231121.3 (6)H21—C126—H20109.5221
O231—C232—C231123.9 (6)H22—C131—C132106.7520
O231—C232—O232124.0 (6)H22—C131—C133106.7218
O232—C232—C231112.0 (5)C131—C133—H23109.1061
C121—N121—C115124.1 (6)H23—C133—C134108.8573
N121—C121—C122108.5 (5)C133—C134—H26109.4161
N121—C121—C123111.2 (5)C133—C134—H24109.2460
N131—C122—C121117.4 (6)C133—C134—H25109.5920
C131—N131—C122117.3 (5)H23—C133—C135108.9184
C136—N131—C122124.8 (5)C133—C135—H27109.5346
N131—C131—C132110.0 (6)C133—C135—H29109.2093
N131—C131—C133112.6 (5)C133—C135—H28109.4751
C136—N131—C131117.5 (5)H26—C134—H24109.4733
C221—N221—C215120.9 (5)H25—C134—H24109.5218
N221—C221—C222106.5 (5)H26—C134—H25109.5776
N221—C221—C223111.9 (5)H29—C135—H27109.4748
N231—C222—C221118.3 (5)H28—C135—H27109.4735
C231—N231—C222120.4 (5)H29—C135—H28109.6598
C236—N231—C222124.2 (5)H31—C136—H30109.5050
N231—C231—C232109.6 (5)H32—C136—H30109.4780
N231—C231—C233112.1 (5)H32—C136—H31109.5131
C236—N231—C231115.4 (5)C211—C212—H33109.2703
C113—C111—C112109.3 (6)C211—C212—H35109.3605
C114—C111—C112111.2 (6)C211—C212—H34109.7826
C114—C111—C113113.0 (5)C211—C213—H36109.5048
C123—C121—C122111.9 (5)C211—C213—H38109.2669
C121—C123—C125108.5 (5)C211—C213—H37109.7014
C121—C123—C124113.6 (6)C211—C214—H39109.5477
C125—C123—C124114.0 (6)C211—C214—H41109.3646
C123—C125—C126114.2 (6)C211—C214—H40109.5189
C133—C131—C132113.6 (5)H35—C212—H33109.4745
C131—C133—C134109.6 (5)H34—C212—H33109.4892
C131—C133—C135109.7 (6)H35—C212—H34109.4497
C135—C133—C134110.6 (6)H38—C213—H36109.4735
C213—C211—C212111.8 (7)H37—C213—H36109.5459
C214—C211—C212109.2 (6)H38—C213—H37109.3342
C214—C211—C213115.5 (6)H41—C214—H39109.4702
C223—C221—C222109.5 (5)H40—C214—H39109.4500
C221—C223—C224108.6 (6)H41—C214—H40109.4759
C221—C223—C225109.9 (5)H42—C221—C222109.6144
C225—C223—C224112.4 (6)H42—C221—C223109.5952
C223—C225—C226112.9 (6)C221—C223—H43108.4718
C233—C231—C232113.1 (5)C223—C224—H46109.4399
C231—C233—C234110.1 (5)H43—C223—C224108.5887
C231—C233—C235111.2 (5)C223—C224—H44109.5769
C235—C233—C234109.3 (5)C223—C224—H45109.5491
H132—O132—C132104.2114H43—C223—C225108.7077
H232—O232—C232116.7971C223—C225—H47108.5442
H121—N121—C115118.0068C223—C225—H48108.6487
N121—C121—H12108.3786H46—C224—H44109.4698
H121—N121—C121117.9162H45—C224—H44109.4162
N131—C131—H22106.6753H46—C224—H45109.3753
N131—C136—H31109.4108H47—C225—C226108.4536
N131—C136—H30109.4029H48—C225—C226108.7486
N131—C136—H32109.5174C225—C226—H49109.0712
H221—N221—C215119.5022C225—C226—H51109.8485
H221—N221—C221119.5899C225—C226—H50109.5193
N221—C221—H42109.6533H48—C225—H47109.4551
N231—C231—H52107.1065H51—C226—H49109.4735
N231—C236—H61109.5250H50—C226—H49109.5866
N231—C236—H60109.2712H51—C226—H50109.3284
N231—C236—H62109.5820H52—C231—C232107.4437
C111—C112—H3109.2695H52—C231—C233107.1467
C111—C112—H5109.5519C231—C233—H53108.7817
C111—C112—H4109.4369C233—C234—H56109.3953
C111—C113—H6109.6080H53—C233—C234108.6683
C111—C113—H8109.5476C233—C234—H54109.5880
C111—C113—H7109.2860C233—C234—H55109.5211
C111—C114—H9109.6206H53—C233—C235108.7831
C111—C114—H11109.2778C233—C235—H57109.1681
C111—C114—H10109.5624C233—C235—H59109.6322
H5—C112—H3109.4694C233—C235—H58109.4549
H4—C112—H3109.6067H56—C234—H54109.4678
H5—C112—H4109.4927H55—C234—H54109.4366
H8—C113—H6109.4724H56—C234—H55109.4184
H7—C113—H6109.4615H59—C235—H57109.4720
H8—C113—H7109.4515H58—C235—H57109.5736
H11—C114—H9109.4836H59—C235—H58109.5261
H10—C114—H9109.3743H61—C236—H60109.4880
H11—C114—H10109.5087H62—C236—H60109.4706
H12—C121—C122108.2631H62—C236—H61109.4903
C115—O111—C111—C112174.7 (5)N121—C121—C122—N131150.6 (6)
C115—O111—C111—C11368.8 (7)C123—C121—C122—O12194.9 (7)
C115—O111—C111—C11455.7 (7)C123—C121—C122—N13186.3 (7)
C111—O111—C115—O11222.1 (9)N121—C121—C123—C12469.5 (7)
C111—O111—C115—N121157.2 (5)N121—C121—C123—C12558.5 (7)
C215—O211—C211—C212173.6 (5)C122—C121—C123—C12452.1 (7)
C215—O211—C211—C21368.8 (7)C122—C121—C123—C125179.9 (4)
C215—O211—C211—C21458.8 (7)C121—C123—C125—C126163.3 (6)
C211—O211—C215—O2125.2 (10)C124—C123—C125—C12668.9 (8)
C211—O211—C215—N221174.2 (5)N131—C131—C132—O131103.6 (8)
C121—N121—C115—O1114.0 (8)N131—C131—C132—O13276.3 (8)
C121—N121—C115—O112176.6 (6)C133—C131—C132—O131129.1 (8)
C115—N121—C121—C12285.7 (7)C133—C131—C132—O13251.0 (8)
C115—N121—C121—C123150.8 (6)N131—C131—C133—C13454.1 (7)
C131—N131—C122—O1217.8 (9)N131—C131—C133—C135175.7 (6)
C131—N131—C122—C121171.1 (5)C132—C131—C133—C134180.0 (5)
C136—N131—C122—O121179.3 (6)C132—C131—C133—C13558.4 (7)
C136—N131—C122—C1211.8 (9)N221—C221—C222—O22154.0 (8)
C122—N131—C131—C132113.4 (6)N221—C221—C222—N231125.6 (6)
C122—N131—C131—C133118.7 (6)C223—C221—C222—O22167.1 (7)
C136—N131—C131—C13273.1 (7)C223—C221—C222—N231113.3 (6)
C136—N131—C131—C13354.7 (7)N221—C221—C223—C22461.2 (6)
C221—N221—C215—O211174.5 (5)N221—C221—C223—C225175.5 (5)
C221—N221—C215—O2125.6 (10)C222—C221—C223—C224179.0 (5)
C215—N221—C221—C22280.9 (6)C222—C221—C223—C22557.6 (6)
C215—N221—C221—C223159.5 (5)C221—C223—C225—C226174.6 (6)
C231—N231—C222—O2210.5 (8)C224—C223—C225—C22664.2 (7)
C231—N231—C222—C221179.1 (5)N231—C231—C232—O231111.2 (7)
C236—N231—C222—O221177.5 (6)N231—C231—C232—O23265.6 (6)
C236—N231—C222—C2212.9 (9)C233—C231—C232—O23114.7 (9)
C222—N231—C231—C232112.0 (6)C233—C231—C232—O232168.5 (5)
C222—N231—C231—C233121.5 (6)N231—C231—C233—C23450.4 (7)
C236—N231—C231—C23266.1 (6)N231—C231—C233—C235171.6 (5)
C236—N231—C231—C23360.3 (6)C232—C231—C233—C234174.9 (5)
N121—C121—C122—O12128.2 (9)C232—C231—C233—C23563.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N221—H221···O131i0.982.032.897 (7)147
O132—H132···O221ii0.781.912.650 (6)157
N121—H121···O231iii0.981.992.946 (7)164
O232—H232···O112iv0.821.842.656 (6)177
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z1; (iv) x1, y, z+1.
 

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