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The title pentapeptide, Boc
0—Gly
1–Δ
ZPhe
2—Gly
3–Δ
EPhe
4—Gly
5—OMe, C
30H
35N
5O
8·2H
2O, adopts the type I β-turn conformation for the Δ
ZPhe
2—Gly
3 residues. It is stabilized by a
intramolecular hydrogen bond between the Δ
EPhe
4 NH and Gly
1 CO groups. All the amino acid residues in the pentapeptide sequence are linked
trans to each other. The crystal structure is stabilized by intra- and intermolecular hydrogen bonds.
Supporting information
CCDC reference: 298540
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.012 Å
- R factor = 0.072
- wR factor = 0.114
- Data-to-parameter ratio = 9.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.63 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 116.00 A 3
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.146
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT213_ALERT_2_C Atom C1 has ADP max/min Ratio ............. 3.30 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.65 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.96 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23
PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
PLAT741_ALERT_1_C Bond Calc 0.86(6), Rep 0.86000 ...... Missing su
O9 -H9A 1.555 1.555
PLAT741_ALERT_1_C Bond Calc 0.87(5), Rep 0.86000 ...... Missing su
O9 -H9B 1.555 1.555
PLAT741_ALERT_1_C Bond Calc 0.86(5), Rep 0.86000 ...... Missing su
O10 -H10A 1.555 1.555
PLAT741_ALERT_1_C Bond Calc 0.87(3), Rep 0.86000 ...... Missing su
O10 -H10B 1.555 1.555
PLAT742_ALERT_1_C Angle Calc 105(7), Rep 105.00 ...... Missing su
H9A -O9 -H9B 1.555 1.555 1.555
PLAT742_ALERT_1_C Angle Calc 91(8), Rep 91.00 ...... Missing su
H10A -O10 -H10B 1.555 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.86(6), Rep 0.86000 ...... Missing su
O9 -H9A 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.87(5), Rep 0.86000 ...... Missing su
O9 -H9B 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.86(5), Rep 0.86000 ...... Missing su
O10 -H10A 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.87(3), Rep 0.86000 ...... Missing su
O10 -H10B 1.555 1.555
PLAT746_ALERT_1_C H...A Calc 2.09(7), Rep 2.09000 ...... Missing su
H9A -O4 1.555 1.555
PLAT746_ALERT_1_C H...A Calc 2.07(7), Rep 2.07000 ...... Missing su
H9B -O10 1.555 1.554
PLAT746_ALERT_1_C H...A Calc 2.16(6), Rep 2.16000 ...... Missing su
H10A -O7 1.555 1.556
PLAT746_ALERT_1_C H...A Calc 2.08(2), Rep 2.09000 ...... Missing su
H10B -O5 1.555 1.555
PLAT748_ALERT_1_C D-H..A Calc 143(7), Rep 143.00 ...... Missing su
O9 -H9A -O4 1.555 1.555 1.555
PLAT748_ALERT_1_C D-H..A Calc 177(9), Rep 177.00 ...... Missing su
O10 -H10B -O5 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C30 H35 N5 O8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
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 76.73
From the CIF: _reflns_number_total 3775
Count of symmetry unique reflns 3912
Completeness (_total/calc) 96.50%
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
3 ALERT level B = Potentially serious problem
29 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
18 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
7 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
N-[
tert-Butoxycarbonylglycyl-(
Z)-
α,
β-dehydrophenylalanylglycyl- (E)-
α,
β-dehydrophenylalanyl]glycine methyl ester
dihydrate
top
Crystal data top
C30H35N5O8·2H2O | F(000) = 1336 |
Mr = 629.66 | Dx = 1.274 Mg m−3 |
Orthorhombic, P 21 21 2 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2 2ab | Cell parameters from 5475 reflections |
a = 15.371 (4) Å | θ = 3–73° |
b = 23.889 (6) Å | µ = 0.81 mm−1 |
c = 8.940 (3) Å | T = 100 K |
V = 3282.7 (16) Å3 | Needle, colourless |
Z = 4 | 0.04 × 0.03 × 0.01 mm |
Data collection top
Xcalibur PX κ-geometry diffractometer CCD detector | 3775 independent reflections |
Radiation source: fine-focus sealed tube | 1835 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.146 |
ω and φ scans | θmax = 76.7°, θmin = 3.4° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003) | h = −19→15 |
Tmin = 0.910, Tmax = 0.983 | k = −30→22 |
22419 measured reflections | l = −9→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/σ2(Fo2) |
3775 reflections | (Δ/σ)max = 0.001 |
417 parameters | Δρmax = 0.40 e Å−3 |
4 restraints | Δρmin = −0.32 e Å−3 |
Special details top
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 accuracy 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.7579 (6) | 0.5031 (3) | −0.1559 (13) | 0.048 (3) | |
C2 | 0.8257 (5) | 0.5432 (3) | −0.2195 (12) | 0.058 (3) | |
H2A | 0.8223 | 0.5430 | −0.3290 | 0.086* | |
H2B | 0.8839 | 0.5313 | −0.1880 | 0.086* | |
H2C | 0.8143 | 0.5811 | −0.1824 | 0.086* | |
C3 | 0.7576 (8) | 0.5008 (4) | 0.0126 (10) | 0.069 (4) | |
H3A | 0.7125 | 0.4747 | 0.0463 | 0.103* | |
H3B | 0.7456 | 0.5381 | 0.0527 | 0.103* | |
H3C | 0.8146 | 0.4880 | 0.0482 | 0.103* | |
C4A | 0.6559 (11) | 0.5097 (7) | −0.1864 (19) | 0.029 (4)* | 0.50 |
H4A1 | 0.5969 | 0.4953 | −0.2023 | 0.043* | 0.50 |
H4A2 | 0.6534 | 0.5430 | −0.1223 | 0.043* | 0.50 |
H4A3 | 0.6914 | 0.4809 | −0.1380 | 0.043* | 0.50 |
C4B | 0.6757 (11) | 0.5174 (7) | −0.260 (2) | 0.039 (5)* | 0.50 |
H4B1 | 0.6635 | 0.4878 | −0.3335 | 0.058* | 0.50 |
H4B2 | 0.7388 | 0.5216 | −0.2489 | 0.058* | 0.50 |
H4B3 | 0.6508 | 0.5528 | −0.2956 | 0.058* | 0.50 |
O1 | 0.7760 (4) | 0.4441 (2) | −0.2208 (7) | 0.0435 (19) | |
O2 | 0.9111 (4) | 0.4382 (2) | −0.1193 (9) | 0.061 (2) | |
C5 | 0.8520 (6) | 0.4201 (3) | −0.1951 (12) | 0.033 (2) | |
O3 | 0.8417 (3) | 0.2565 (2) | −0.2510 (7) | 0.0256 (14) | |
N1 | 0.8562 (4) | 0.3704 (2) | −0.2660 (9) | 0.034 (2) | |
H1 | 0.8104 | 0.3579 | −0.3150 | 0.041* | |
C6 | 0.9355 (5) | 0.3370 (3) | −0.2624 (10) | 0.029 (2) | |
H6A | 0.9747 | 0.3514 | −0.1834 | 0.035* | |
H6B | 0.9660 | 0.3402 | −0.3596 | 0.035* | |
C7 | 0.9140 (5) | 0.2758 (3) | −0.2316 (10) | 0.027 (2) | |
N2 | 0.9834 (4) | 0.2460 (2) | −0.1819 (7) | 0.0236 (16) | |
H2 | 1.0340 | 0.2631 | −0.1752 | 0.028* | |
C8 | 0.9786 (5) | 0.1881 (3) | −0.1395 (9) | 0.0219 (18) | |
C16 | 0.8990 (5) | 0.1711 (3) | −0.0568 (10) | 0.026 (2) | |
O4 | 0.8645 (3) | 0.1247 (2) | −0.0785 (7) | 0.0321 (15) | |
C9 | 1.0444 (5) | 0.1527 (3) | −0.1501 (9) | 0.0213 (19) | |
H9 | 1.0344 | 0.1161 | −0.1122 | 0.026* | |
C10 | 1.1311 (5) | 0.1631 (3) | −0.2132 (10) | 0.028 (2) | |
C11 | 1.1445 (5) | 0.1909 (3) | −0.3478 (9) | 0.026 (2) | |
H11A | 1.0956 | 0.2064 | −0.3978 | 0.032* | |
C12 | 1.2269 (5) | 0.1972 (3) | −0.4136 (10) | 0.031 (2) | |
H12A | 1.2340 | 0.2147 | −0.5084 | 0.037* | |
C13 | 1.2970 (5) | 0.1770 (3) | −0.3343 (11) | 0.036 (2) | |
H13A | 1.3535 | 0.1812 | −0.3758 | 0.043* | |
C14 | 1.2889 (5) | 0.1512 (3) | −0.1985 (10) | 0.030 (2) | |
H14A | 1.3388 | 0.1393 | −0.1443 | 0.036* | |
C15 | 1.2039 (5) | 0.1424 (3) | −0.1406 (10) | 0.033 (2) | |
H15A | 1.1969 | 0.1220 | −0.0502 | 0.040* | |
N3 | 0.8699 (4) | 0.2065 (2) | 0.0507 (7) | 0.0213 (16) | |
H3 | 0.8958 | 0.2390 | 0.0628 | 0.026* | |
O5 | 0.6422 (3) | 0.1902 (2) | 0.1579 (6) | 0.0230 (13) | |
C17 | 0.7966 (4) | 0.1918 (3) | 0.1470 (9) | 0.0228 (19) | |
H17A | 0.8004 | 0.2145 | 0.2393 | 0.027* | |
H17B | 0.8027 | 0.1520 | 0.1764 | 0.027* | |
C18 | 0.7077 (5) | 0.1997 (3) | 0.0806 (9) | 0.0187 (18) | |
O6 | 0.4788 (3) | 0.1952 (2) | −0.1176 (6) | 0.0273 (14) | |
N4 | 0.7044 (4) | 0.2190 (3) | −0.0583 (8) | 0.0244 (17) | |
H4 | 0.7536 | 0.2241 | −0.1066 | 0.029* | |
C19 | 0.6249 (5) | 0.2322 (3) | −0.1338 (10) | 0.0220 (19) | |
C27 | 0.5574 (5) | 0.1871 (4) | −0.1370 (10) | 0.031 (2) | |
C20 | 0.6194 (5) | 0.2833 (3) | −0.1921 (9) | 0.025 (2) | |
H20 | 0.6660 | 0.3073 | −0.1643 | 0.030* | |
C21 | 0.5544 (5) | 0.3102 (4) | −0.2921 (10) | 0.029 (2) | |
C22 | 0.5621 (5) | 0.3682 (3) | −0.3053 (11) | 0.034 (2) | |
H22A | 0.6066 | 0.3870 | −0.2514 | 0.041* | |
C23 | 0.5048 (6) | 0.4000 (4) | −0.3978 (12) | 0.056 (3) | |
H23A | 0.5117 | 0.4393 | −0.4080 | 0.067* | |
C24 | 0.4382 (6) | 0.3717 (4) | −0.4732 (11) | 0.042 (3) | |
H24A | 0.3998 | 0.3918 | −0.5367 | 0.051* | |
C25 | 0.4282 (5) | 0.3146 (4) | −0.4556 (9) | 0.029 (2) | |
H25A | 0.3811 | 0.2958 | −0.5030 | 0.035* | |
C26 | 0.4868 (5) | 0.2846 (3) | −0.3686 (10) | 0.028 (2) | |
H26A | 0.4803 | 0.2452 | −0.3613 | 0.033* | |
O7 | 0.4980 (4) | 0.1059 (2) | −0.4190 (7) | 0.0357 (16) | |
C29 | 0.4849 (5) | 0.0808 (4) | −0.3049 (11) | 0.030 (2) | |
C28 | 0.5317 (5) | 0.0863 (3) | −0.1573 (10) | 0.033 (2) | |
H28A | 0.4886 | 0.0905 | −0.0756 | 0.040* | |
H28B | 0.5660 | 0.0520 | −0.1379 | 0.040* | |
N5 | 0.5894 (4) | 0.1349 (2) | −0.1591 (8) | 0.0248 (17) | |
H5 | 0.6454 | 0.1302 | −0.1747 | 0.030* | |
O8 | 0.4222 (3) | 0.0411 (2) | −0.2882 (7) | 0.0339 (16) | |
C30 | 0.3726 (5) | 0.0289 (3) | −0.4235 (10) | 0.041 (3) | |
H30A | 0.3293 | −0.0001 | −0.4020 | 0.061* | |
H30B | 0.4122 | 0.0156 | −0.5018 | 0.061* | |
H30C | 0.3432 | 0.0630 | −0.4577 | 0.061* | |
O9 | 0.7442 (4) | 0.1008 (3) | −0.3096 (8) | 0.0365 (17) | |
H9A | 0.787 (3) | 0.119 (3) | −0.270 (9) | 0.044* | |
H9B | 0.738 (5) | 0.115 (3) | −0.398 (4) | 0.044* | |
O10 | 0.6561 (4) | 0.1664 (3) | 0.4805 (8) | 0.0417 (18) | |
H10A | 0.609 (3) | 0.147 (3) | 0.481 (10) | 0.050* | |
H10B | 0.650 (6) | 0.173 (3) | 0.386 (2) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.048 (7) | 0.011 (4) | 0.084 (9) | 0.003 (4) | −0.014 (7) | −0.014 (6) |
C2 | 0.077 (8) | 0.020 (5) | 0.075 (9) | 0.001 (5) | 0.022 (7) | 0.003 (6) |
C3 | 0.115 (12) | 0.029 (6) | 0.063 (9) | 0.010 (7) | 0.010 (8) | −0.007 (7) |
O1 | 0.027 (4) | 0.029 (3) | 0.074 (6) | 0.013 (3) | −0.021 (4) | −0.015 (4) |
O2 | 0.055 (5) | 0.041 (4) | 0.088 (7) | 0.019 (4) | −0.042 (5) | −0.026 (4) |
C5 | 0.030 (5) | 0.019 (4) | 0.051 (7) | 0.005 (4) | −0.006 (5) | −0.007 (4) |
O3 | 0.015 (3) | 0.029 (3) | 0.032 (4) | −0.001 (3) | −0.002 (3) | 0.006 (3) |
N1 | 0.020 (4) | 0.026 (4) | 0.055 (6) | 0.011 (3) | −0.019 (4) | −0.010 (4) |
C6 | 0.023 (4) | 0.020 (4) | 0.045 (6) | 0.006 (4) | 0.006 (4) | 0.006 (4) |
C7 | 0.026 (5) | 0.028 (4) | 0.026 (6) | 0.007 (4) | 0.007 (4) | 0.007 (4) |
N2 | 0.009 (3) | 0.027 (4) | 0.034 (5) | 0.002 (3) | −0.006 (3) | 0.004 (3) |
C8 | 0.022 (4) | 0.023 (4) | 0.020 (5) | 0.000 (4) | 0.003 (4) | −0.003 (4) |
C16 | 0.023 (4) | 0.029 (5) | 0.025 (6) | −0.004 (4) | −0.008 (4) | −0.001 (4) |
O4 | 0.021 (3) | 0.030 (3) | 0.045 (4) | −0.006 (3) | 0.001 (3) | 0.003 (3) |
C9 | 0.019 (4) | 0.015 (4) | 0.030 (5) | 0.003 (3) | 0.003 (4) | 0.004 (4) |
C10 | 0.015 (4) | 0.033 (5) | 0.035 (6) | 0.007 (4) | 0.000 (4) | −0.005 (4) |
C11 | 0.029 (5) | 0.033 (5) | 0.017 (5) | −0.001 (4) | −0.006 (4) | −0.010 (4) |
C12 | 0.028 (5) | 0.039 (5) | 0.026 (6) | −0.005 (4) | 0.003 (4) | 0.001 (4) |
C13 | 0.023 (5) | 0.040 (5) | 0.046 (7) | 0.004 (4) | 0.008 (5) | −0.010 (5) |
C14 | 0.020 (4) | 0.031 (5) | 0.039 (6) | 0.006 (4) | 0.003 (4) | −0.009 (5) |
C15 | 0.026 (5) | 0.030 (5) | 0.042 (6) | 0.004 (4) | 0.000 (5) | −0.007 (5) |
N3 | 0.014 (3) | 0.024 (4) | 0.025 (4) | −0.002 (3) | 0.001 (3) | −0.002 (3) |
O5 | 0.012 (3) | 0.024 (3) | 0.033 (4) | 0.005 (2) | 0.003 (3) | −0.001 (3) |
C17 | 0.014 (4) | 0.024 (4) | 0.031 (5) | −0.001 (4) | −0.002 (4) | −0.001 (4) |
C18 | 0.023 (4) | 0.015 (4) | 0.018 (5) | 0.003 (4) | −0.007 (4) | −0.005 (3) |
O6 | 0.011 (3) | 0.031 (3) | 0.040 (4) | 0.005 (3) | 0.004 (3) | 0.001 (3) |
N4 | 0.008 (3) | 0.032 (4) | 0.034 (5) | 0.002 (3) | 0.000 (3) | −0.001 (4) |
C19 | 0.010 (4) | 0.028 (4) | 0.028 (5) | −0.003 (3) | −0.004 (4) | −0.007 (4) |
C27 | 0.016 (4) | 0.036 (5) | 0.040 (6) | 0.005 (4) | 0.001 (4) | −0.002 (5) |
C20 | 0.021 (4) | 0.037 (5) | 0.018 (5) | 0.005 (4) | −0.003 (4) | −0.003 (4) |
C21 | 0.018 (4) | 0.038 (5) | 0.030 (6) | 0.003 (4) | 0.000 (4) | 0.003 (5) |
C22 | 0.033 (5) | 0.025 (5) | 0.044 (6) | 0.007 (4) | −0.016 (5) | −0.007 (5) |
C23 | 0.047 (7) | 0.044 (6) | 0.076 (10) | 0.023 (5) | −0.027 (7) | −0.004 (6) |
C24 | 0.026 (5) | 0.054 (7) | 0.047 (7) | 0.021 (5) | 0.001 (5) | −0.001 (6) |
C25 | 0.017 (4) | 0.048 (6) | 0.021 (5) | −0.007 (4) | 0.000 (4) | −0.010 (5) |
C26 | 0.009 (4) | 0.038 (5) | 0.037 (6) | −0.001 (4) | −0.006 (4) | −0.001 (4) |
O7 | 0.031 (4) | 0.044 (4) | 0.033 (4) | −0.008 (3) | −0.001 (3) | −0.004 (3) |
C29 | 0.014 (4) | 0.035 (5) | 0.040 (6) | 0.003 (4) | −0.004 (4) | 0.007 (5) |
C28 | 0.028 (5) | 0.035 (5) | 0.037 (6) | −0.010 (4) | −0.010 (4) | 0.002 (5) |
N5 | 0.019 (4) | 0.021 (3) | 0.035 (5) | −0.003 (3) | −0.003 (3) | 0.000 (3) |
O8 | 0.024 (3) | 0.038 (4) | 0.040 (4) | −0.006 (3) | −0.010 (3) | 0.006 (3) |
C30 | 0.047 (6) | 0.033 (5) | 0.042 (7) | −0.004 (5) | −0.016 (6) | −0.009 (5) |
O9 | 0.023 (3) | 0.049 (4) | 0.038 (5) | −0.007 (3) | 0.005 (3) | 0.001 (4) |
O10 | 0.033 (4) | 0.050 (4) | 0.042 (5) | −0.013 (3) | −0.004 (4) | 0.013 (4) |
Geometric parameters (Å, º) top
C1—C3 | 1.507 (14) | C14—H14A | 0.9500 |
C1—C2 | 1.526 (11) | C15—H15A | 0.9500 |
C1—O1 | 1.549 (9) | N3—C17 | 1.461 (8) |
C1—C4A | 1.600 (18) | N3—H3 | 0.88 |
C1—C4B | 1.61 (2) | O5—C18 | 1.242 (9) |
C2—H2A | 0.98 | C17—C18 | 1.501 (9) |
C2—H2B | 0.98 | C17—H17A | 0.9900 |
C2—H2C | 0.98 | C17—H17B | 0.9900 |
C3—H3A | 0.98 | C18—N4 | 1.326 (10) |
C3—H3B | 0.98 | O6—C27 | 1.236 (8) |
C3—H3C | 0.98 | N4—C19 | 1.430 (9) |
C4A—H4A1 | 0.98 | N4—H4 | 0.88 |
C4A—H4A2 | 0.98 | C19—C20 | 1.332 (10) |
C4A—H4A3 | 0.98 | C19—C27 | 1.495 (10) |
C4B—H4B1 | 0.98 | C27—N5 | 1.357 (9) |
C4B—H4B2 | 0.98 | C20—C21 | 1.486 (10) |
C4B—H4B3 | 0.98 | C20—H20 | 0.9500 |
O1—C5 | 1.321 (9) | C21—C26 | 1.386 (10) |
O2—C5 | 1.214 (10) | C21—C22 | 1.396 (10) |
C5—N1 | 1.347 (9) | C22—C23 | 1.426 (11) |
O3—C7 | 1.216 (8) | C22—H22A | 0.9500 |
N1—C6 | 1.457 (8) | C23—C24 | 1.399 (12) |
N1—H1 | 0.88 | C23—H23A | 0.9500 |
C6—C7 | 1.525 (9) | C24—C25 | 1.382 (11) |
C6—H6A | 0.99 | C24—H24A | 0.9500 |
C6—H6B | 0.9900 | C25—C26 | 1.389 (10) |
C7—N2 | 1.357 (9) | C25—H25A | 0.9500 |
N2—C8 | 1.437 (8) | C26—H26A | 0.9500 |
N2—H2 | 0.88 | O7—C29 | 1.199 (10) |
C8—C9 | 1.321 (9) | C29—O8 | 1.361 (9) |
C8—C16 | 1.486 (10) | C29—C28 | 1.509 (11) |
C16—O4 | 1.243 (8) | C28—N5 | 1.460 (8) |
C16—N3 | 1.357 (10) | C28—H28A | 0.9900 |
C9—C10 | 1.468 (9) | C28—H28B | 0.9900 |
C9—H9 | 0.9500 | N5—H5 | 0.88 |
C10—C15 | 1.385 (10) | O8—C30 | 1.459 (10) |
C10—C11 | 1.391 (11) | C30—H30A | 0.9800 |
C11—C12 | 1.405 (10) | C30—H30B | 0.9800 |
C11—H11A | 0.9500 | C30—H30C | 0.9800 |
C12—C13 | 1.377 (10) | O9—H9A | 0.86 |
C12—H12A | 0.9500 | O9—H9B | 0.86 |
C13—C14 | 1.367 (11) | O10—H10A | 0.86 |
C13—H13A | 0.9500 | O10—H10B | 0.86 |
C14—C15 | 1.420 (10) | | |
| | | |
C3—C1—C2 | 113.4 (9) | C12—C13—H13A | 118.5 |
C3—C1—O1 | 110.0 (8) | C13—C14—C15 | 118.2 (9) |
C2—C1—O1 | 108.0 (8) | C13—C14—H14A | 120.9 |
C3—C1—C4A | 99.8 (11) | C15—C14—H14A | 120.9 |
C2—C1—C4A | 122.9 (10) | C10—C15—C14 | 121.4 (9) |
O1—C1—C4A | 101.7 (8) | C10—C15—H15A | 119.3 |
C3—C1—C4B | 125.9 (12) | C14—C15—H15A | 119.3 |
C2—C1—C4B | 100.7 (10) | C16—N3—C17 | 121.4 (7) |
O1—C1—C4B | 96.7 (9) | C16—N3—H3 | 119.3 |
C1—C2—H2A | 109.5 | C17—N3—H3 | 119.3 |
C1—C2—H2B | 109.5 | N3—C17—C18 | 116.0 (7) |
H2A—C2—H2B | 109.5 | N3—C17—H17A | 108.3 |
C1—C2—H2C | 109.5 | C18—C17—H17A | 108.3 |
H2A—C2—H2C | 109.5 | N3—C17—H17B | 108.3 |
H2B—C2—H2C | 109.5 | C18—C17—H17B | 108.3 |
C1—C3—H3A | 109.5 | H17A—C17—H17B | 107.4 |
C1—C3—H3B | 109.5 | O5—C18—N4 | 123.6 (7) |
H3A—C3—H3B | 109.5 | O5—C18—C17 | 119.7 (7) |
C1—C3—H3C | 109.5 | N4—C18—C17 | 116.7 (7) |
H3A—C3—H3C | 109.5 | C18—N4—C19 | 123.5 (7) |
H3B—C3—H3C | 109.5 | C18—N4—H4 | 118.3 |
C1—C4A—H4A1 | 153.7 | C19—N4—H4 | 118.3 |
C1—C4A—H4A2 | 91.1 | C20—C19—N4 | 116.1 (7) |
H4A1—C4A—H4A2 | 109.5 | C20—C19—C27 | 127.5 (8) |
C1—C4A—H4A3 | 46.2 | N4—C19—C27 | 116.4 (7) |
H4A1—C4A—H4A3 | 109.5 | O6—C27—N5 | 121.2 (8) |
H4A2—C4A—H4A3 | 109.5 | O6—C27—C19 | 124.3 (8) |
C1—C4B—H4B1 | 112.6 | N5—C27—C19 | 114.4 (7) |
H4B1—C4B—H4B2 | 109.5 | C19—C20—C21 | 132.4 (8) |
C1—C4B—H4B3 | 132.6 | C19—C20—H20 | 113.8 |
H4B1—C4B—H4B3 | 109.5 | C21—C20—H20 | 113.8 |
H4B2—C4B—H4B3 | 109.5 | C26—C21—C22 | 117.3 (8) |
C5—O1—C1 | 119.3 (7) | C26—C21—C20 | 127.6 (8) |
O2—C5—O1 | 127.1 (8) | C22—C21—C20 | 115.0 (8) |
O2—C5—N1 | 122.8 (8) | C21—C22—C23 | 121.7 (8) |
O1—C5—N1 | 110.1 (8) | C21—C22—H22A | 119.2 |
C5—N1—C6 | 120.8 (7) | C23—C22—H22A | 119.2 |
C5—N1—H1 | 119.6 | C24—C23—C22 | 118.3 (9) |
C6—N1—H1 | 119.6 | C24—C23—H23A | 120.9 |
N1—C6—C7 | 110.3 (6) | C22—C23—H23A | 120.9 |
N1—C6—H6A | 109.6 | C25—C24—C23 | 120.3 (9) |
C7—C6—H6A | 109.6 | C25—C24—H24A | 119.9 |
N1—C6—H6B | 109.6 | C23—C24—H24A | 119.9 |
C7—C6—H6B | 109.6 | C24—C25—C26 | 120.0 (8) |
H6A—C6—H6B | 108.1 | C24—C25—H25A | 120.0 |
O3—C7—N2 | 124.6 (8) | C26—C25—H25A | 120.0 |
O3—C7—C6 | 122.4 (7) | C21—C26—C25 | 122.4 (8) |
N2—C7—C6 | 113.1 (7) | C21—C26—H26A | 118.8 |
C7—N2—C8 | 123.4 (7) | C25—C26—H26A | 118.8 |
C7—N2—H2 | 118.3 | O7—C29—O8 | 124.1 (8) |
C8—N2—H2 | 118.3 | O7—C29—C28 | 128.4 (8) |
C9—C8—N2 | 123.8 (7) | O8—C29—C28 | 107.6 (8) |
C9—C8—C16 | 119.4 (7) | N5—C28—C29 | 110.4 (7) |
N2—C8—C16 | 115.9 (7) | N5—C28—H28A | 109.6 |
O4—C16—N3 | 121.7 (8) | C29—C28—H28A | 109.6 |
O4—C16—C8 | 121.1 (8) | N5—C28—H28B | 109.6 |
N3—C16—C8 | 117.0 (7) | C29—C28—H28B | 109.6 |
C8—C9—C10 | 128.0 (7) | H28A—C28—H28B | 108.1 |
C8—C9—H9 | 116.0 | C27—N5—C28 | 120.6 (7) |
C10—C9—H9 | 116.0 | C27—N5—H5 | 119.7 |
C15—C10—C11 | 117.1 (8) | C28—N5—H5 | 119.7 |
C15—C10—C9 | 119.6 (8) | C29—O8—C30 | 114.7 (7) |
C11—C10—C9 | 123.2 (7) | O8—C30—H30A | 109.5 |
C10—C11—C12 | 123.2 (8) | O8—C30—H30B | 109.5 |
C10—C11—H11A | 118.4 | H30A—C30—H30B | 109.5 |
C12—C11—H11A | 118.4 | O8—C30—H30C | 109.5 |
C13—C12—C11 | 116.8 (8) | H30A—C30—H30C | 109.5 |
C13—C12—H12A | 121.6 | H30B—C30—H30C | 109.5 |
C11—C12—H12A | 121.6 | H9A—O9—H9B | 105 |
C14—C13—C12 | 123.0 (9) | H10A—O10—H10B | 91 |
C14—C13—H13A | 118.5 | | |
| | | |
C3—C1—O1—C5 | −64.4 (12) | C8—C16—N3—C17 | −174.9 (7) |
C2—C1—O1—C5 | 59.9 (12) | C16—N3—C17—C18 | −80.2 (9) |
C4A—C1—O1—C5 | −169.5 (10) | N3—C17—C18—O5 | −177.2 (7) |
C4B—C1—O1—C5 | 163.5 (10) | N3—C17—C18—N4 | 0.2 (10) |
C1—O1—C5—O2 | 2.8 (16) | O5—C18—N4—C19 | 1.3 (12) |
C1—O1—C5—N1 | −177.4 (8) | C17—C18—N4—C19 | −176.0 (6) |
O2—C5—N1—C6 | −3.9 (15) | C18—N4—C19—C20 | 126.5 (9) |
O1—C5—N1—C6 | 176.3 (8) | C18—N4—C19—C27 | −52.9 (11) |
C5—N1—C6—C7 | 135.2 (9) | C20—C19—C27—O6 | −41.1 (15) |
N1—C6—C7—O3 | 19.3 (13) | N4—C19—C27—O6 | 138.3 (9) |
N1—C6—C7—N2 | −161.0 (7) | C20—C19—C27—N5 | 140.8 (9) |
O3—C7—N2—C8 | −2.9 (14) | N4—C19—C27—N5 | −39.9 (11) |
C6—C7—N2—C8 | 177.4 (7) | N4—C19—C20—C21 | 171.5 (8) |
C7—N2—C8—C9 | 151.1 (9) | C27—C19—C20—C21 | −9.2 (16) |
C7—N2—C8—C16 | −39.2 (11) | C19—C20—C21—C26 | −10.1 (16) |
C9—C8—C16—O4 | −47.0 (12) | C19—C20—C21—C22 | 167.9 (9) |
N2—C8—C16—O4 | 142.8 (8) | C26—C21—C22—C23 | −2.1 (14) |
C9—C8—C16—N3 | 128.1 (8) | C20—C21—C22—C23 | 179.7 (8) |
N2—C8—C16—N3 | −42.1 (10) | C21—C22—C23—C24 | 1.7 (15) |
N2—C8—C9—C10 | −4.2 (14) | C22—C23—C24—C25 | 1.0 (15) |
C16—C8—C9—C10 | −173.5 (8) | C23—C24—C25—C26 | −3.1 (15) |
C8—C9—C10—C15 | 138.0 (9) | C22—C21—C26—C25 | 0.0 (14) |
C8—C9—C10—C11 | −44.9 (13) | C20—C21—C26—C25 | 177.9 (8) |
C15—C10—C11—C12 | 1.9 (12) | C24—C25—C26—C21 | 2.7 (14) |
C9—C10—C11—C12 | −175.2 (7) | O7—C29—C28—N5 | 9.9 (14) |
C10—C11—C12—C13 | −3.5 (12) | O8—C29—C28—N5 | −170.1 (6) |
C11—C12—C13—C14 | 0.8 (13) | O6—C27—N5—C28 | −1.4 (14) |
C12—C13—C14—C15 | 3.2 (13) | C19—C27—N5—C28 | 176.8 (7) |
C11—C10—C15—C14 | 2.3 (12) | C29—C28—N5—C27 | 79.8 (10) |
C9—C10—C15—C14 | 179.5 (7) | O7—C29—O8—C30 | 2.4 (12) |
C13—C14—C15—C10 | −4.8 (12) | C28—C29—O8—C30 | −177.7 (7) |
O4—C16—N3—C17 | 0.2 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O3 | 0.88 | 2.03 | 2.869 (8) | 160 |
N3—H3···O6i | 0.88 | 2.08 | 2.944 (8) | 166 |
N2—H2···O5i | 0.88 | 2.01 | 2.885 (7) | 174 |
N5—H5···O9 | 0.88 | 2.06 | 2.853 (9) | 149 |
O9—H9A···O4 | 0.86 | 2.09 | 2.831 (9) | 143 |
O9—H9B···O10ii | 0.86 | 2.07 | 2.794 (9) | 141 |
O10—H10A···O7iii | 0.86 | 2.16 | 2.967 (9) | 156 |
O10—H10B···O5 | 0.86 | 2.09 | 2.947 (9) | 177 |
C2—H2B···O2 | 0.98 | 2.35 | 2.970 (10) | 121 |
C3—H3C···O2 | 0.98 | 2.42 | 3.031 (12) | 120 |
C6—H6A···O2 | 0.99 | 2.36 | 2.761 (9) | 103 |
N4—H4···N3 | 0.88 | 2.31 | 2.741 (8) | 110 |
N5—H5···N4 | 0.88 | 2.53 | 2.825 (8) | 100 |
C26—H26A···O6 | 0.95 | 2.48 | 3.101 (10) | 122 |
C28—H28A···O2iv | 0.99 | 2.22 | 3.145 (11) | 155 |
C28—H28B···O8v | 0.99 | 2.60 | 3.337 (10) | 131 |
C28—H28A···O2iv | 0.99 | 2.22 | 3.145 (11) | 155 |
C26—H26A···O6 | 0.95 | 2.48 | 3.101 (10) | 122 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x−1/2, −y+1/2, −z; (v) −x+1, −y, z. |
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